DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
REQUIREMENT FOR UNITY OF INVENTION
As provided in 37 CFR 1.475(a), a national stage application shall relate to one invention only or to a group of inventions so linked as to form a single general inventive concept (“requirement of unity of invention”). Where a group of inventions is claimed in a national stage application, the requirement of unity of invention shall be fulfilled only when there is a technical relationship among those inventions involving one or more of the same or corresponding special technical features. The expression “special technical features” shall mean those technical features that define a contribution which each of the claimed inventions, considered as a whole, makes over the prior art.
The determination whether a group of inventions is so linked as to form a single general inventive concept shall be made without regard to whether the inventions are claimed in separate claims or as alternatives within a single claim. See 37 CFR 1.475(e).
When Claims Are Directed to Multiple Categories of Inventions:
As provided in 37 CFR 1.475 (b), a national stage application containing claims to different categories of invention will be considered to have unity of invention if the claims are drawn only to one of the following combinations of categories:
(1) A product and a process specially adapted for the manufacture of said product; or
(2) A product and a process of use of said product; or
(3) A product, a process specially adapted for the manufacture of the said product, and a use of the said product; or
(4) A process and an apparatus or means specifically designed for carrying out the said process; or
(5) A product, a process specially adapted for the manufacture of the said product, and an apparatus or means specifically designed for carrying out the said process.
Otherwise, unity of invention might not be present. See 37 CFR 1.475 (c).
Restriction is required under 35 U.S.C. 121 and 372.
This application contains the following inventions or groups of inventions which are not so linked as to form a single general inventive concept under PCT Rule 13.1.
In accordance with 37 CFR 1.499, applicant is required, in reply to this action, to elect a single invention to which the claims must be restricted.
Group I, claim(s) 1-11 and 16-20, drawn to a process for producing an isocyanate-group terminated polyoxazolidinone composition.
Group II, claim(s) 12, drawn to an isocyanate-group terminated polyoxazolidinone composition produced according to the method of claim 1.
Group III, claim(s) 13 and 14, drawn to a process for producing an isocyanate-group terminated polyoxazolidinone from the isocyanate-group terminated pplyoxazolidinone composition of claim 1.
Group IV, claim(s) 15, drawn to an isocyanate-group terminated polyoxazolidinone produced with the process according to claim 14.
The groups of inventions listed above do not relate to a single general inventive concept under PCT Rule 13.1 because, under PCT Rule 13.2, they lack the same or corresponding special technical features for the following reasons:
Groups I-IV lack unity of invention because even though the inventions of these groups require the technical feature of an isocyanate-group terminated polyoxazolidinone produced by copolymerizing a polyisocyanate compound (A) with a polyepoxide compound (B) in the presence of a catalyst (C), wherein the polyisocyanate compound (A) comprises two or more isocyanate groups and the polyepoxide compound (B) comprises two or more epoxy groups, wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1, and wherein the catalyst (C) is represented by the formula (I), this technical feature is not a special technical feature as it does not make a contribution over the prior art in view of Muller et al. (US 2017/0081462 A1, cited in IDS). Muller teaches production of polymeric oxazolidinone compounds by reacting an isocyanate compound with an epoxide compound in the presence of a catalyst system [0009], wherein the catalyst is represented by the general formula
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wherein M is phosphorus or antimony, (R1), (R2), (R3), (R4) are independently of one another selected from the group comprising linear or branched alkyl groups containing 1 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents, cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents, C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents and aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms and/or heteroatom containing substituents and/or heteroatoms, Y is a halide, carbonate, nitrate, sulphate, or phosphate anion, and n is an integer of 1, 2, or 3 [0012], where in one embodiment the method is performed in the presence of a solvent [0044], where in another embodiment of the method, the reaction is conducted in the absence of a solvent [0045], wherein the isocyanate compound is an isocyanate compound with two or more NCO groups per molecule, and the epoxide compound is an epoxide compound with two or more epoxy groups per molecule [0050, 0055], wherein the oligomeric or polymeric oxazolidinone compound is obtained using an isocyanate compound with at least two NCO groups per molecule, and an epoxide compound with at least two epoxy groups per molecule [0055], wherein the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], wherein an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], wherein this oligomeric or polymeric oxazolidinone compound comprises at least two terminal isocyanate groups [0059], which reads on an isocyanate-group terminated polyoxazolidinone produced by copolymerizing a polyisocyanate compound (A) with a polyepoxide compound (B) in the presence of a catalyst (C), wherein the polyisocyanate compound (A) comprises two or more isocyanate groups and the polyepoxide compound (B) comprises two or more epoxy groups, wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger or equal to 1:1, and wherein the catalyst (C) is represented by the formula (I) wherein M is phosphorous or antimony, wherein (R1), (R2), (R3), and (R4) are each, independently of one another, a linear or branched alkyl groups containing 1 to 22 carbon atoms, optionally substituted with one or more heteroatoms, heteroatom containing substituents, or a combination thereof, a cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with one or more heteroatoms, heteroatom containing substituents, or a combination thereof, a C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with one or more heteroatoms, heteroatom containing substituents, or a combination thereof, or an aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms, heteroatom containing substituents, one or more heteroatoms, or a combination thereof, wherein Y is a halide, carbonate, nitrate, sulfate, or phosphate, and wherein n is an integer of 1, 2, or 3, and wherein the process is conducted in the absence of a solvent (E) with a boiling point higher than 200 °C at 1 bar (absolute).
Muller does not teach a specific embodiment wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the ratio between Muller’s diisocyanate compound and Muller’s diepoxide compound to be from 2 to 25 moles of Muller’s diisocyanate compound to 1 mole of Muller diisocyanate compound. The proposed modification would read on wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing obtainment of an isocyanate terminated oligomer, and for optimizing the desired chain length of Muller’s polyoxazolidinone compounds because Muller teaches that the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], and that this oligomeric or polymeric oxazolidinone compound comprises at least two terminal isocyanate groups [0059], which means that the ratio between Muller’s diisocyanate compound and Muller’s diepoxide compound in moles of Muller’s diisocyanate compound to mole of Muller diisocyanate compound would have affected obtainment of an isocyanate terminated oligomer and the desired chain length of Muller’s polyoxazolidinone compounds.
During a telephone conversation with Robert J. Sovesky on 05/29/2026 a provisional election was made without traverse to prosecute the invention of Group I, claims 1-11 and 16-20. Affirmation of this election must be made by applicant in replying to this Office action. Claims 12-15 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention.
Applicant is reminded that upon the cancelation of claims to a non-elected invention, the inventorship must be corrected in compliance with 37 CFR 1.48(a) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. A request to correct inventorship under 37 CFR 1.48(a) must be accompanied by an application data sheet in accordance with 37 CFR 1.76 that identifies each inventor by his or her legal name and by the processing fee required under 37 CFR 1.17(i).
The examiner has required restriction between product or apparatus claims and process claims. Where applicant elects claims directed to the product/apparatus, and all product/apparatus claims are subsequently found allowable, withdrawn process claims that include all the limitations of the allowable product/apparatus claims should be considered for rejoinder. All claims directed to a nonelected process invention must include all the limitations of an allowable product/apparatus claim for that process invention to be rejoined.
In the event of rejoinder, the requirement for restriction between the product/apparatus claims and the rejoined process claims will be withdrawn, and the rejoined process claims will be fully examined for patentability in accordance with 37 CFR 1.104. Thus, to be allowable, the rejoined claims must meet all criteria for patentability including the requirements of 35 U.S.C. 101, 102, 103 and 112. Until all claims to the elected product/apparatus are found allowable, an otherwise proper restriction requirement between product/apparatus claims and process claims may be maintained. Withdrawn process claims that are not commensurate in scope with an allowable product/apparatus claim will not be rejoined. See MPEP § 821.04. Additionally, in order for rejoinder to occur, applicant is advised that the process claims should be amended during prosecution to require the limitations of the product/apparatus claims. Failure to do so may result in no rejoinder. Further, note that the prohibition against double patenting rejections of 35 U.S.C. 121 does not apply where the restriction requirement is withdrawn by the examiner before the patent issues. See MPEP § 804.01.
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-11 and 16-20 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites the limitation “a linear or branched alkyl groups” in lines 13-14, which is indefinite because the terms “a” and “groups” make the number of “linear or branched alkyl groups” unclear because “a” is a word referring to one of something, and “groups” means more than one group. For further examination of the claims, this limitation is interpreted as “a linear or branched alkyl group”.
Claim 1 recites the limitation “a cycloaliphatic groups” in lines 15-16, which is indefinite because the terms “a” and “groups” make the number of “cycloaliphatic groups” unclear because “a” is a word referring to one of something, and “groups” means more than one group. For further examination of the claims, this limitation is interpreted as “a cycloaliphatic group”.
Claim 1 recites the limitation “a C1 to C3 alkyl-bridge cycloaliphatic groups” in lines 17-18, which is indefinite because the terms “a” and “groups” make the number of “C1 to C3 alkyl-bridge cycloaliphatic groups” unclear because “a” is a word referring to one of something, and “groups” means more than one group. For further examination of the claims, this limitation is interpreted as “a C1 to C3 alkyl-bridge cycloaliphatic group”.
Claim 1 recites the limitation “an aryl groups” in line 20, which is indefinite because the terms “a” and “groups” make the number of “aryl groups” unclear because “a” is a word referring to one of something, and “groups” means more than one group. For further examination of the claims, this limitation is interpreted as “an aryl group”.
Claim 1 recites the limitation “one or more alkyl groups containing 1 to 10 carbon atoms one or more heteroatom containing substituents one or more heteroatoms, or a combination thereof” in lines 21-22, which is indefinite because there are no commas separating each item in the list of items before the “or a combination thereof”, which makes each item in the list of items unclear. For further examination of the claims, this limitation is interpreted as limitation “one or more alkyl groups containing 1 to 10 carbon atoms, one or more heteroatom containing substituents, one or more heteroatoms, or a combination thereof”.
Claim 7 recites the limitation “butanediole diglycidyl ether” in line 3, which is indefinite because it is not a compound known to one of ordinary skill in the art. For further examination of the claims, this limitation is interpreted as “butanediol diglycidyl ether”.
Claim 10 recites the limitation "the solvent (D) and the solvent (D)" in line 2. There is insufficient antecedent basis for the first recitation of “the solvent (D)” in the claim because claims 1 and 10 do not recite “a solvent (D)”. For further examination of the claims, this limitation is interpreted as “a solvent (D) and the solvent (D)”.
Claim 11 recites the limitation “the reactor” in line 2. There is insufficient antecedent basis for this limitation in the claim because claims 1, 10, and 11 do not recite “a reactor”. For further examination of the claims, this limitation is interpreted as “a reactor”.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-7, 10, 11, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Muller et al. (US 2017/0081462 A1, cited in IDS).
Regarding claim 1, Muller teaches production of polymeric oxazolidinone compounds by reacting an isocyanate compound with an epoxide compound in the presence of a catalyst system [0009], wherein the catalyst is represented by the general formula
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wherein M is phosphorous or antimony, (R1), (R2), (R3), (R4) are independently of one another selected from the group comprising linear or branched alkyl groups containing 1 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents, cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents, C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents and aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms and/or heteroatom containing substituents and/or heteroatoms, whereas (R4) is different from (R1), (R2), and (R3) and is selected from the group comprising branched alkyl groups containing 3 to 22 carbon atoms, C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, and aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms, and/or heteroatom containing substituents and/or heteroatoms, whereas (R1), (R2) are aryl groups containing 6 to 18 carbon atoms, Y is a halide, carbonate, nitrate, sulphate, or phosphate anion, and n is an integer of 1, 2, or 3 [0012], where in one embodiment the method is performed in the presence of a solvent [0044], where in another embodiment of the method, the reaction is conducted in the absence of a solvent [0045], wherein the isocyanate compound is an isocyanate compound with two NCO groups per molecule, and the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], wherein the polymeric oxazolidinone compound is obtained using an isocyanate compound with two NCO groups per molecule, and an epoxide compound with two epoxy groups per molecule, and comprises at least one unit derived from the epoxide compound and at least two units derived from the isocyanate compound [0055], wherein the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], wherein an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], wherein this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], wherein the average chain length of the polyoxazolidinones is adjusted by the relative molar ratio of the diisocyanate and diepoxide used in the particular reaction [0086], wherein when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], wherein the average chain length in the polymeric produced is calculated based on the molar ratios of diisocyanate and diepoxide compound employed [0088], which reads on a process for producing an isocyanate-group terminated polyoxazolidinone composition, the process comprising copolymerizing of a polyisocyanate compound (A) with a polyepoxide compound (B) in the presence of a catalyst (C), wherein the polyisocyanate compound (A) comprises two isocyanate groups and the polyepoxide compound (B) comprises two epoxy groups, wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) Is larger than 1:1, and wherein the catalyst (C) is represented by the formula (I) wherein M is phosphorous or antimony, wherein (R1), (R2), (R3), and (R4) are each, independently of one another, a linear or branched alkyl groups containing 1 to 22 carbon atoms, optionally substituted with one or more heteroatoms, heteroatom containing substituents, or a combination thereof, a cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with one or more heteroatoms, heteroatom containing substituents, or a combination thereof, a C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with one or more heteroatoms, heteroatom containing substituents, or a combination thereof, or an aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms, one or more heteroatom containing substituents, one or more heteroatoms, or a combination thereof, wherein Y is a halide, carbonate, nitrate, sulfate, or phosphate anion, and wherein n is an integer of 1, 2, or 3, and wherein the process is optionally conducted in the absence of a solvent (E) with a boiling point higher than 200 °C at 1 bar (absolute).
Muller does not teach a specific embodiment wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the molar ratio of Muller’s diisocyanate to Muller’s diepoxide that are reacted in production of Muller’s polymeric oxazolidinone compounds to be larger than 2:1 and less than 25:1. The proposed modification would read on wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing obtainment of an isocyanate terminated polyoxazolidinone and for optimizing a desired average chain length of Muller’s polyoxazolidinones because Muller teaches that the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], that this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], that the average chain length of the polyoxazolidinones is adjusted by the relative molar ratio of the diisocyanate and diepoxide used in the particular reaction [0086], that when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], and that the average chain length in the polymeric produced is calculated based on the molar ratios of diisocyanate and diepoxide compound employed [0088], which means that the molar ratio of Muller’s diisocyanate to Muller’s diepoxide that are reacted in production of Muller’s polymeric oxazolidinone compounds would have affected obtainment of an isocyanate terminated polyoxazolidinone and an average chain length of Muller’s polyoxazolidinones.
Muller does not teach a specific embodiment wherein the process is conducted in the absence of a solvent (E) with a boiling point higher than 200 °C at 1 bar (absolute). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to conduct Muller’s reaction in the absence of a solvent. The proposed modification would read on wherein the process is conducted in the absence of a solvent (E) with a boiling point higher than 200 °C at 1 bar (absolute) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for a savings in material costs for Muller’s production of polymeric oxazolidinone compounds by not using a solvent because Muller teaches that in one embodiment the method is performed in the presence of a solvent [0044], that in another embodiment of the method, the reaction is conducted in the absence of a solvent [0045], and that preferably, the reaction mixture contains only the epoxide compound, the isocyanate compound, and the onium salt as well as the oxazolidinone compound formed during the reaction [0045], which means that a solvent is not necessary for Muller’s production of polymeric oxazolidinone compounds.
Regarding claim 2, Muller teaches that the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], that this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], that the average chain length of the polyoxazolidinones is adjusted by the relative molar ratio of the diisocyanate and diepoxide used in the particular reaction [0086], that when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], and that the average chain length in the polymeric produced is calculated based on the molar ratios of diisocyanate and diepoxide compound employed [0088], which reads on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 1:1.
Muller does not teach a specific embodiment wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.6:1 to 7.0:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the molar ratio of Muller’s diisocyanate to Muller’s diepoxide that are reacted in production of Muller’s polymeric oxazolidinone compounds to be from 2.6:1 to 7.0:1. The proposed modification would read on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.6:1 to 7.0:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing obtainment of an isocyanate terminated polyoxazolidinone and for optimizing a desired average chain length of Muller’s polyoxazolidinones because Muller teaches that the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], that this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], that the average chain length of the polyoxazolidinones is adjusted by the relative molar ratio of the diisocyanate and diepoxide used in the particular reaction [0086], that when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], and that the average chain length in the polymeric produced is calculated based on the molar ratios of diisocyanate and diepoxide compound employed [0088], which means that the molar ratio of Muller’s diisocyanate to Muller’s diepoxide that are reacted in production of Muller’s polymeric oxazolidinone compounds would have affected obtainment of an isocyanate terminated polyoxazolidinone and an average chain length of Muller’s polyoxazolidinones.
Regarding claim 3, Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that the diisocyanate is tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, tolylene-α,4-diisocyanate, 2,4,6-trimethyl-1,3-phenylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, 1,3-bis(1-isocyanato-1-methylethyl)benzene, 3,3′-dimethyl-4,4′-biphenylene diisocyanate, naphthalene-1,5-diisocyanate, 1,3-phenylene diisocyanate, 1,4-diisocyanatobenzene, 2,4- or 2,5- or 2,6-diisocyanatotoluene (TDI) or mixtures of these isomers, 4,4′-, 2,4′- or 2,2′-diisocyanatodiphenylmethane (MDI) or mixtures of these isomers, 4,4′-, 2,4′- or 2,2′-diisocyanato-2,2-diphenylpropane-p-xylene diisocyanate and α,α,α′,α′-tetramethyl-m- or -p-xylene diisocyanate (TMXDI), mixtures thereof [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022], which reads on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) and/or an aromatic polyisocyanate compound (A-2) as claimed.
Regarding claim 4, Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that the diepoxide compound is butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether, 1,2-dihydroxybenzene diglycidyl ether, resorcinol diglycidyl ether, 1,4-dihydroxybenzene diglycidyl ether, bisphenol-A diglycidyl ether, diglycidyl ethers of polybutadiene bisphenol-A-block-copolymers, diglycidyl o-phthalate, diglycidyl isophthalate, diglycidyl terephthalate [0026], or a mixture of two or more of the aforementioned diepoxides [0028], which reads on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) and/or aromatic polyepoxide compound (B-2) as claimed.
Regarding claim 5, Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that optionally the diisocyanate is tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, mixtures thereof [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022], which optionally reads on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed. Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that optionally the diepoxide compound is butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether [0026], or a mixture of two or more of the aforementioned diepoxides [0028], which optionally reads on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed.
Muller does not teach a specific embodiment wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, mixtures thereof, or a mixture of two or more of the aforementioned polyisocyanates as Muller’s diisocyanate. The proposed modification would read on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Muller’s polymeric oxazolidinone compounds due to Muller’s diisocyanate being aliphatic instead of aromatic, because aliphatic compounds are more flexible than aromatic compounds, because aromatic compounds are more rigid than aliphatic compounds, and because Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that optionally the diisocyanate is tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, mixtures thereof [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diisocyanate that is suitable for Muller’s production of polymeric oxazolidinone compounds and/or because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Muller does not teach a specific embodiment wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether, or a mixture of two or more of the aforementioned diepoxides as Muller’s diepoxide compound. The proposed modification would read on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Muller’s polymeric oxazolidinone compounds due to Muller’s diepoxide compound being aliphatic instead of aromatic, because aliphatic compounds are more flexible than aromatic compounds, because aromatic compounds are more rigid than aliphatic compounds, and because Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that optionally the diepoxide compound is butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether [0026], or a mixture of two or more of the aforementioned diepoxides [0028]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diepoxide compound that is suitable for Muller’s production of polymeric oxazolidinone compounds and/or because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 6, Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that optionally the diisocyanate is hexamethylene diisocyanate, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI) [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022], which optionally reads on wherein the aliphatic polyisocyanate compound (A-1) is one or more compounds selected from 1,6-diisocyanatohexane, and 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane as claimed.
Muller does not teach a specific embodiment wherein the aliphatic polyisocyanate compound (A-1) is one or more compound selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s hexamethylene diisocyanate, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), or a mixture of two or more of the aforementioned polyisocyanates as Muller’s diisocyanate. The proposed modification would read on wherein the aliphatic polyisocyanate compound (A-1) is one or more compounds selected from 1,6-diisocyanatohexane, and 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Muller’s polymeric oxazolidinone compounds due to Muller’s hexamethylene diisocyanate, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), or a mixture of two or more of the aforementioned polyisocyanates being aliphatic instead of aromatic, because aliphatic compounds are more flexible than aromatic compounds, because aromatic compounds are more rigid than aliphatic compounds, and because Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that optionally the diisocyanate is hexamethylene diisocyanate, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI) [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diisocyanate that is suitable for Muller’s production of polymeric oxazolidinone compounds and/or because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 7, Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that optionally the diepoxide compound is ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether [0026], or a mixture of two or more of the aforementioned diepoxides [0028], which optionally reads on wherein the aliphatic polyepoxide compound (B-1) is one or more compounds selected from ethanediol diglycidyl ether, and hexane diol diglycidyl ether as claimed.
Muller does not teach a specific embodiment wherein the aliphatic polyepoxide compound (B-1) is one or more compounds selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, or a mixture of two or more of the aforementioned diepoxides as Muller’s diepoxide compound. The proposed modification would read on wherein the aliphatic polyepoxide compound (B-1) is one or more compounds selected from ethanediol diglycidyl ether, and hexane diol diglycidyl ether as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Muller’s polymeric oxazolidinone compounds due to Muller’s diepoxide compound being aliphatic instead of aromatic, because aliphatic compounds are more flexible than aromatic compounds, because aromatic compounds are more rigid than aliphatic compounds, and because Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that optionally the diepoxide compound is ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether [0026], or a mixture of two or more of the aforementioned diepoxides [0028]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diepoxide compound that is suitable for Muller’s production of polymeric oxazolidinone compounds and/or because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 10, Muller teaches that in one embodiment the method is performed in the presence of a solvent [0044], and that suitable solvents are chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, or mixtures of one or more of the aforementioned solvents among each other [0044], which optionally reads on wherein the copolymerization is in the solvent (D) and the solvent (D) is one or more compounds selected from chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, and N,N-dimethylacetamide as claimed.
Muller does not teach that the copolymerization is in the solvent (D) and the solvent (D) is one or more compounds selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to conduct Muller’s reaction in the presence of a solvent and to select Muller’s chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, or mixtures of one or more of the aforementioned solvents among each other as Muller’s solvent. The proposed modification would read on wherein the copolymerization is in the solvent (D) and the solvent (D) is one or more compounds selected from chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, and N,N-dimethylacetamide as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for improving processability of Muller’s production of polymeric oxazolidinone compounds and for providing a species of solvent that is suitable for Muller’s production of polymeric oxazolidinone compounds because Muller teaches that in one embodiment the method is performed in the presence of a solvent [0044], and that suitable solvents are chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, or mixtures of one or more of the aforementioned solvents among each other [0044].
Regarding claim 11, Muller teaches production of polymeric oxazolidinone compounds by reacting an isocyanate compound with an epoxide compound in the presence of a catalyst system [0009], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], that this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], that a pressurized reactor is used in the synthesis of polyoxazolidinones [0070], that when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], that in one embodiment the method is performed in the presence of a solvent [0044], that suitable solvents are chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, or mixtures of one or more of the aforementioned solvents among each other [0044], that preferably, the isocyanate compound is added to the reaction mixture consisting of epoxide compound, isocyanate compound, onium salt, and oxazolidinone compound, but not considering solvent, if present, with an addition rate [0048], that in an example the reactor was charged with diepoxide and catalyst, that dry solvent NMP was added, that the reactor was sealed and the mixture was heated, that a solution of diisocyanate in dry solvent NMP was added, that after an overall reaction time starting with the addition of diisocyanate, and that the reaction mixture was cooled [0143], which suggests the process according to claim 10 comprising a) placing the solvent (D) and the catalyst (C) in the reactor to provide a mixture (a), (b) placing the polyisocyanate compound (A) and the polyepoxide compound (B) is a second vessel to provide a mixture (b), and c) adding the mixture (b) to the mixture (a) to form an isocyanate-group terminated polyoxazolidinone composition (c) as claimed.
Muller does not teach that the process comprises a) placing the solvent (D) and the catalyst (C) in the reactor to provide a mixture (a), (b) placing the polyisocyanate compound (A) and the polyepoxide compound (B) is a second vessel to provide a mixture (b), and c) adding the mixture (b) to the mixture (a) to form an isocyanate-group terminated polyoxazolidinone composition (c). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to conduct Muller’s reaction in the presence of a solvent and to select Muller’s chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, or mixtures of one or more of the aforementioned solvents among each other as Muller’s solvent, by placing Muller’s solvent and Muller’s catalyst system in a first of Muller’s reactor to provide a mixture, placing Muller’s isocyanate compound and Muller’s epoxide compound in a second of Muller’s reactor to provide a mixture, and adding the mixture of Muller’s isocyanate compound and Muller’s epoxide compound to the mixture of Muller’s solvent and Muller’s catalyst system, and reacting Muller’s isocyanate compound with Muller’s epoxide compound in the presence of Muller’s catalyst system to produce Muller’s polymeric oxazolidinone compound comprising two terminal isocyanate groups. The proposed modification would read on the process according to claim 10 comprising a) placing the solvent (D) and the catalyst (C) in the reactor to provide a mixture (a), (b) placing the polyisocyanate compound (A) and the polyepoxide compound (B) is a second vessel to provide a mixture (b), and c) adding the mixture (b) to the mixture (a) to form an isocyanate-group terminated polyoxazolidinone composition (c) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for improving processability of Muller’s production of polymeric oxazolidinone compounds, and for providing a species of solvent that is suitable for Muller’s production of polymeric oxazolidinone compounds because Muller teaches that in one embodiment the method is performed in the presence of a solvent [0044], that suitable solvents are chlorobenzene, the different isomers of dichlorobenzene, dimethylformamide, N,N-dimethylacetamide, or mixtures of one or more of the aforementioned solvents among each other [0044], that preferably, the isocyanate compound is added to the reaction mixture consisting of epoxide compound, isocyanate compound, onium salt, and oxazolidinone compound, but not considering solvent, if present, with an addition rate [0048], that in an example the reactor was charged with diepoxide and catalyst, that dry solvent NMP was added, that the reactor was sealed and the mixture was heated, that a solution of diisocyanate in dry solvent NMP was added, that after an overall reaction time starting with the addition of diisocyanate, and that the reaction mixture was cooled [0143], which means that the proposed modification also would have been beneficial for modifying processability of Muller’s production of polymeric oxazolidinone compounds.
Regarding claim 16, Muller teaches that M is optionally phosphorus [0012], which optionally reads on wherein M is phosphorous as claimed.
Muller does not teach a specific embodiment wherein M is phosphorous. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s M to be phosphorous. The proposed modification would read on wherein M is phosphorous as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying catalyzing properties of Muller’s production of polymeric oxazolidinone compounds because Muller teaches that the catalyst is represented by the general formula
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wherein M is optionally phosphorous [0012]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 17, Muller teaches that Y is a halide or carbonate [0012], which optionally reads on wherein Y is a halide or a carbonate as claimed.
Muller does not teach a specific embodiment wherein Y is a halide or a carbonate. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s Y to be a halide or carbonate. The proposed modification would read on wherein Y is a halide or a carbonate as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying catalyzing properties of Muller’s production of polymeric oxazolidinone compounds because Muller teaches that the catalyst is represented by the general formula
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wherein Y is a halide or carbonate [0012]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 18, Muller teaches that the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], that this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], that the average chain length of the polyoxazolidinones is adjusted by the relative molar ratio of the diisocyanate and diepoxide used in the particular reaction [0086], that when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], and that the average chain length in the polymeric produced is calculated based on the molar ratios of diisocyanate and diepoxide compound employed [0088], which reads on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 1:1.
Muller does not teach a specific embodiment wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.8:1 to 5.5:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the molar ratio of Muller’s diisocyanate to Muller’s diepoxide that are reacted in production of Muller’s polymeric oxazolidinone compounds to be from 2.8:1 to 5.5:1. The proposed modification would read on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.8:1 to 5.5:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing obtainment of an isocyanate terminated polyoxazolidinone and for optimizing a desired average chain length of Muller’s polyoxazolidinones because Muller teaches that the chain length of the polyoxazolidinone compounds can be controlled by adjusting the ratio between the diisocyanate and the diepoxide compound [0056], that an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0056], that this polymeric oxazolidinone compound comprises two terminal isocyanate groups [0059], that the average chain length of the polyoxazolidinones is adjusted by the relative molar ratio of the diisocyanate and diepoxide used in the particular reaction [0086], that when an isocyanate terminated polyoxazolidinone is desired, the diisocyanate is used in excess [0088], and that the average chain length in the polymeric produced is calculated based on the molar ratios of diisocyanate and diepoxide compound employed [0088], which means that the molar ratio of Muller’s diisocyanate to Muller’s diepoxide that are reacted in production of Muller’s polymeric oxazolidinone compounds would have affected obtainment of an isocyanate terminated polyoxazolidinone and an average chain length of Muller’s polyoxazolidinones.
Regarding claim 19, Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that optionally the diisocyanate is tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, mixtures thereof [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022], which optionally reads on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed.
Muller does not teach a specific embodiment wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, mixtures thereof, or a mixture of two or more of the aforementioned polyisocyanates as Muller’s diisocyanate. The proposed modification would read on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Muller’s polymeric oxazolidinone compounds due to Muller’s diisocyanate being aliphatic instead of aromatic, because aliphatic compounds are more flexible than aromatic compounds, because aromatic compounds are more rigid than aliphatic compounds, and because Muller teaches that the isocyanate compound is an isocyanate compound with two NCO groups per molecule [0050, 0055], and that optionally the diisocyanate is tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), 2-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate (THDI), dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,3,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI), 4,4′-diisocyanatodicyclohexylmethane (H12-MDI), 4,4′-diisocyanato-3,3′-dimethyldicyclohexylmethane, 4,4′-diisocyanato-2,2-dicyclohexylpropane, poly(hexamethylene diisocyanate), octamethylene diisocyanate, 1,4-diisocyanatobutane, 1,8-diisocyanatooctane, mixtures thereof [0020], or a mixture of two or more of the aforementioned polyisocyanates [0022]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diisocyanate that is suitable for Muller’s production of polymeric oxazolidinone compounds and/or because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 20, Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that optionally the diepoxide compound is butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether [0026], or a mixture of two or more of the aforementioned diepoxides [0028], which optionally reads on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed.
Muller does not teach a specific embodiment wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Muller’s butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether, or a mixture of two or more of the aforementioned diepoxides as Muller’s diepoxide compound. The proposed modification would read on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Muller’s polymeric oxazolidinone compounds due to Muller’s diepoxide compound being aliphatic instead of aromatic, because aliphatic compounds are more flexible than aromatic compounds, because aromatic compounds are more rigid than aliphatic compounds, and because Muller teaches that the epoxide compound is an epoxide compound with two epoxy groups per molecule [0050, 0055], and that optionally the diepoxide compound is butadiene diepoxide, vinylcyclohexene diepoxide, limonene diepoxide, the diepoxides of double unsaturated fatty acid C1-C18 alkyl esters, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, polybutadiene diglycidyl ether, 1,6-hexanediol diglycidyl ether, hydrogenated bisphenol-A diglycidyl ether [0026], or a mixture of two or more of the aforementioned diepoxides [0028]. Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of diepoxide compound that is suitable for Muller’s production of polymeric oxazolidinone compounds and/or because it would have been obvious to try with a reasonable expectation of success based on Muller’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Claims 1-6, 8, 10, 11, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Clarke (US 3,687,897).
Regarding claims 1 and 16, Clarke teaches a process for the preparation of oxazolidinones which comprises reacting a vicinal epoxide containing compound with an organic isocyanate compound in the presence of a phosphonium catalyst (1:7-18), wherein the product contains multiple oxazolidinone groups and unreacted isocyanate groups, and a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:66-5:5), wherein in some instances, it is often advantageous to conduct the reaction in the presence of an inert solvent (5:23-29), wherein suitable inert solvents include o-dichlorobenzene, or dimethylformamide (5:29-30), wherein suitable phosphonium catalysts include methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, methyltrioctylphosphonium dimethylphosphate, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59), which reads on a process for producing an isocyanate-group terminated polyoxazolidinone composition, the process comprising copolymerizing of a polyisocyanate compound (A) with a polyepoxide compound (B) in the presence of a catalyst (C), wherein the polyisocyanate compound (A) comprises two or more isocyanate groups and the polyepoxide compound (B) comprises two or more epoxy groups, wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 1:1, and wherein the catalyst (C) is optionally represented by the formula (I), wherein M is phosphorous, wherein (R1), (R2), (R3), and (R4) are each, independently of one another, a linear alkyl groups containing 1 to 4 or 8 carbon atoms, a cycloaliphatic groups containing 6 carbon atoms, or an aryl group containing 6 carbon atoms, wherein Y is a halide, or phosphate anion, and wherein n is 1, wherein M is phosphorous, wherein Y is a halide.
Clarke does not teach a specific embodiment wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize Clarke’s NCO:epoxide ratio in Clarke’s process to be larger than 2:1 and less than 25:1. The proposed modification would read on wherein a molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 2:1 and less than 25:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the yield of a product containing multiple oxazolidinone groups and unreacted isocyanate groups from Clarke’s process because Clarke teaches that the product contains multiple oxazolidinone groups and unreacted isocyanate groups, and that a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:65-5:5), which means that Clarke’s NCO:epoxide ratio in Clarke’s process would have affected yield of a product containing multiple oxazolidinone groups and unreacted isocyanate groups from Clarke’s process.
Clarke does not teach a specific embodiment wherein the catalyst (C) is represented by the formula (I). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, methyltrioctylphosphonium dimethylphosphate, or tetra(3,3-dimethylbutyl)phosphonium chloride as Clarke’s phosphonium catalyst. The proposed modification would read on wherein the catalyst (C) is represented by the formula (I), wherein M is phosphorous, wherein (R1), (R2), (R3), and (R4) are each, independently of one another, a linear alkyl groups containing 1 to 4 or 8 carbon atoms, a cycloaliphatic groups containing 6 carbon atoms, or an aryl group containing 6 carbon atoms, wherein Y is a halide, or phosphate anion, and wherein n is 1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying catalyzing properties in Clarke’s process because Clarke teaches that the suitable phosphonium catalysts include methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, methyltrioctylphosphonium dimethylphosphate, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of catalyst that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 2, Clarke teaches that the product contains multiple oxazolidinone groups and unreacted isocyanate groups, and that a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:66-5:5), which reads on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 1:1.
Clarke does not teach a specific embodiment wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.6:1 to 7.0:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize Clarke’s NCO:epoxide ratio in Clarke’s process to be from 2.6:1 to 7.0:1. The proposed modification would read on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.6:1 to 7.0:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the yield of a product containing multiple oxazolidinone groups and unreacted isocyanate groups from Clarke’s process because Clarke teaches that the product contains multiple oxazolidinone groups and unreacted isocyanate groups, and that a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:65-5:5), which means that Clarke’s NCO:epoxide ratio in Clarke’s process would have affected yield of a product containing multiple oxazolidinone groups and unreacted isocyanate groups from Clarke’s process.
Regarding claim 3, Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are the aliphatic and aromatic isocyanates (3:40-41), which reads on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) and/or an aromatic polyisocyanate compound (A-2) as claimed.
Regarding claim 4, Clarke teaches that the vicinal epoxide containing compound (1:7-8) is a compound or a mixture of compounds having a plurality of vicinal epoxide groups (5:1-3) and that suitable epoxide containing compounds include polyepoxides, such as the polyglycidyl ethers of polyhydric compounds such as, for example, polyhydric phenols, bisphenols, and polyhydric aliphatic compounds (1:46-54), which reads on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) and/or aromatic polyepoxide compound (B-2) as claimed.
Regarding claim 5, Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are the aliphatic isocyanates (3:40-41), which optionally reads on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed. Clarke teaches that the vicinal epoxide containing compound (1:7-8) is a compound or a mixture of compounds having a plurality of vicinal epoxide groups (5:1-3) and that suitable epoxide containing compounds include polyepoxides, such as the polyglycidyl ethers of polyhydric compounds such as, for example, polyhydric aliphatic compounds (1:46-54), which optionally reads on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed.
Clarke does not teach a specific embodiment wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s organic isocyanate compound that is a compound or mixture of compounds having a plurality of isocyanate groups to be aliphatic isocyanates. The proposed modification would read on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Clarke’s oxazolidinones because aliphatic isocyanates are more flexible than aromatic isocyanates, because aromatic isocyanates are more rigid than aliphatic isocyanates, and because Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are the aliphatic isocyanates (3:40-41). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of organic isocyanate compound that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Clarke does not teach a specific embodiment wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s vicinal epoxide containing compound that is a compound or a mixture of compounds having a plurality of vicinal epoxide groups to be polyglycidyl ethers of polyhydric aliphatic compounds. The proposed modification would read on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Clarke’s oxazolidinones because polyglycidyl ethers of polyhydric aliphatic compounds are more flexible than polyglycidyl ethers of polyhydric phenols or bisphenols, because polyglycidyl ethers of polyhydric phenols or bisphenols are more rigid than polyglycidyl ethers of polyhydric aliphatic compounds, and because Clarke teaches that the vicinal epoxide containing compound (1:7-8) is a compound or a mixture of compounds having a plurality of vicinal epoxide groups (5:1-3) and that suitable epoxide containing compounds include polyepoxides, such as the polyglycidyl ethers of polyhydric compounds such as, for example, polyhydric aliphatic compounds (1:46-54). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of vicinal epoxide that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 6, Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are hexamethylene diisocyanate (3:40-42, 51), which optionally reads on wherein the aliphatic polyisocyanate compound (A-1) is one compound selected from 1,6-diisocyanatohexane as claimed.
Clarke does not teach a specific embodiment wherein the aliphatic polyisocyanate compound (A-1) is one or more compounds selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s organic isocyanate compound that is a compound or mixture of compounds having a plurality of isocyanate groups to be hexamethylene diisocyanate. The proposed modification would read on wherein the aliphatic polyisocyanate compound (A-1) is one compound selected from 1,6-diisocyanatohexane as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Clarke’s oxazolidinones because hexamethylene diisocyanate is more flexible than aromatic isocyanates, because aromatic isocyanates are more rigid than hexamethylene diisocyanate, and because Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are hexamethylene diisocyanate (3:40-42, 51). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of organic isocyanate compound that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 8, Clarke teaches that Clarke teaches that suitable phosphonium catalysts include tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59), which optionally reads on wherein the catalyst (C) comprises a tetraalkylphosphonium halogenide as claimed.
Clarke does not teach a specific embodiment wherein the catalyst (C) comprises a tetraalkylphosphonium halogenide, a tetracycloalkylphosphonium halogenide, a tetraarylphosphonium halogenide, or a combination thereof. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, or tetra(3,3-dimethylbutyl)phosphonium chloride as Clarke’s phosphonium catalyst. The proposed modification would read on wherein the catalyst (C) comprises a tetraalkylphosphonium halogenide as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying catalyzing properties in Clarke’s process because Clarke teaches that the suitable phosphonium catalysts include tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of catalyst that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 10, Clarke teaches that in some instances, it is often advantageous to conduct the reaction in the presence of an inert solvent (5:23-29), and that suitable inert solvents include o-dichlorobenzene, or dimethylformamide (5:29-30), which optionally reads on wherein the copolymerization is in the solvent (D) and the solvent (D) is one or more compound selected from the different isomers of dichlorobenzene, and dimethylformamide as claimed.
Clarke does not teach a specific embodiment wherein the copolymerization is in the solvent (D) and the solvent (D) is one or more compounds selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to conduct Clarke’s reaction in the presence of Clarke’s inert solvent that is o-dichlorobenzene or dimethylformamide. The proposed modification would read on wherein the copolymerization is in the solvent (D) and the solvent (D) is one or more compound selected from the different isomers of dichlorobenzene, and dimethylformamide as claimed. One of ordinary skill in art would have been motivated to do so because Clarke teaches that in some instances, it is often advantageous to conduct the reaction in the presence of an inert solvent (5:23-29), and that suitable inert solvents include o-dichlorobenzene, or dimethylformamide (5:29-30), which would have been beneficial for improving processability of Clarke’s process.
Regarding claim 11, Clarke teaches that the process for the preparation of oxazolidinones comprises reacting a vicinal epoxide containing compound with an organic isocyanate compound in the presence of a phosphonium catalyst (1:7-18), that the product contains multiple oxazolidinone groups and unreacted isocyanate groups, that a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:66-5:5), that in some instances, it is often advantageous to conduct the reaction in the presence of an inert solvent (5:23-29), that suitable inert solvents include o-dichlorobenzene, or dimethylformamide (5:29-30), that in an example, anhydrous methanol was added to a reaction vessel, that dimethylformamide solvent plus toluene diisocyanate was added to this, that diglycidyl ether of 4,4’-isopropylidene diphenol was added to keep in solution the carbamate product being formed, that after addition of the toluene diisocyanate, the mixture was heated after which reaction was essentially complete, that the remainder of the diglycidyl ether of 4,4’-isopropylidine diphenol plus tetrabutyl phosphonium bromide catalyst was added, that the reaction mixture was heated, that the methanol that was released was allowed to distil out of the system, that at the end of this reaction period, dimethylformamide solvent was added, and that the reaction mixture cooled (11:50-12:10), which suggests the process according to claim 10 comprising a) placing the solvent (D) and the catalyst (C) in the reactor to provide a mixture (a), (b) placing the polyisocyanate compound (A) and the polyepoxide compound (B) is a second vessel to provide a mixture (b), and c) adding the mixture (b) to the mixture (a) to form an isocyanate-group terminated polyoxazolidinone composition (c) as claimed.
Clarke does not teach that the process comprises a) placing the solvent (D) and the catalyst (C) in the reactor to provide a mixture (a), (b) placing the polyisocyanate compound (A) and the polyepoxide compound (B) is a second vessel to provide a mixture (b), and c) adding the mixture (b) to the mixture (a) to form an isocyanate-group terminated polyoxazolidinone composition (c). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to conduct Clarke’s reaction in the presence of Clarke’s inert solvent that is o-dichlorobenzene or dimethylformamide by placing Clarke’s inert solvent and Clarke’s phosphonium catalyst in a first of Clarke’s reaction vessel to provide a mixture, placing Clarke’s organic isocyanate compound and Clarke’s vicinal epoxide containing compound in a second of Clarke’s reaction vessel to provide a mixture, adding the mixture of Clarke’s organic isocyanate compound and Clarke’s vicinal epoxide containing compound to the mixture of Clarke’s inert solvent and Clarke’s phosphonium catalyst, and conducting Clarke’s reaction such that the product contains multiple oxazolidinone groups and unreacted isocyanate groups. The proposed modification would read on the process according to claim 10 comprising a) placing the solvent (D) and the catalyst (C) in the reactor to provide a mixture (a), (b) placing the polyisocyanate compound (A) and the polyepoxide compound (B) is a second vessel to provide a mixture (b), and c) adding the mixture (b) to the mixture (a) to form an isocyanate-group terminated polyoxazolidinone composition (c) as claimed. One of ordinary skill in art would have been motivated to do so because Clarke teaches that in some instances, it is often advantageous to conduct the reaction in the presence of an inert solvent (5:23-29), that suitable inert solvents include o-dichlorobenzene, or dimethylformamide (5:29-30), that in an example, anhydrous methanol was added to a reaction vessel, that dimethylformamide solvent plus toluene diisocyanate was added to this, that diglycidyl ether of 4,4’-isopropylidene diphenol was added to keep in solution the carbamate product being formed, that after addition of the toluene diisocyanate, the mixture was heated after which reaction was essentially complete, that the remainder of the diglycidyl ether of 4,4’-isopropylidine diphenol plus tetrabutyl phosphonium bromide catalyst was added, that the reaction mixture was heated, that the methanol that was released was allowed to distil out of the system, that at the end of this reaction period, dimethylformamide solvent was added, and that the reaction mixture cooled (11:50-12:10), which would have been beneficial for improving processability of Clarke’s process, and which means that the proposed modification would have been beneficial for modifying processability of Clarke’s process.
Regarding claim 17, Clarke teaches that suitable phosphonium catalysts include methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59), which optionally reads on wherein Y is a halide as claimed.
Clarke does not teach a specific embodiment wherein Y is a halide or a carbonate. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, or tetra(3,3-dimethylbutyl)phosphonium chloride as Clarke’s phosphonium catalyst. The proposed modification would read on wherein Y is a halide as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying catalyzing properties in Clarke’s process because Clarke teaches that the suitable phosphonium catalysts include methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of catalyst that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 18, Clarke teaches that the product contains multiple oxazolidinone groups and unreacted isocyanate groups, and that a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:66-5:5), which reads on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is larger than 1:1.
Clarke does not teach a specific embodiment wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.8:1 to 5.5:1. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize Clarke’s NCO:epoxide ratio in Clarke’s process to be from 2.8:1 to 5.5:1. The proposed modification would read on wherein the molar ratio of the isocyanate groups of the polyisocyanate compound (A) to the epoxy groups of the polyepoxide compound (B) is from 2.8:1 to 5.5:1 as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the yield of a product containing multiple oxazolidinone groups and unreacted isocyanate groups from Clarke’s process because Clarke teaches that the product contains multiple oxazolidinone groups and unreacted isocyanate groups, and that a compound or mixture of compounds having a plurality of isocyanate groups are reacted with a compound or mixture of compounds having a plurality of vicinal epoxide groups by the process in proportions such that the NCO:epoxide ratio is greater than 1:1 (4:65-5:5), which means that Clarke’s NCO:epoxide ratio in Clarke’s process would have affected yield of a product containing multiple oxazolidinone groups and unreacted isocyanate groups from Clarke’s process.
Regarding claim 19, Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are the aliphatic isocyanates (3:40-41), which optionally reads on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed.
Clarke does not teach a specific embodiment wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s organic isocyanate compound that is a compound or mixture of compounds having a plurality of isocyanate groups to be aliphatic isocyanates. The proposed modification would read on wherein the polyisocyanate compound (A) is an aliphatic polyisocyanate compound (A-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Clarke’s oxazolidinones because aliphatic isocyanates are more flexible than aromatic isocyanates, because aromatic isocyanates are more rigid than aliphatic isocyanates, and because Clarke teaches that the organic isocyanate compound (1:8-17) is a compound or mixture of compounds having a plurality of isocyanate groups (4:68-5:1) and that suitable organic isocyanate compounds are the aliphatic isocyanates (3:40-41). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of organic isocyanate compound that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 20, Clarke teaches that the vicinal epoxide containing compound (1:7-8) is a compound or a mixture of compounds having a plurality of vicinal epoxide groups (5:1-3) and that suitable epoxide containing compounds include polyepoxides, such as the polyglycidyl ethers of polyhydric compounds such as, for example, polyhydric aliphatic compounds (1:46-54), which optionally reads on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed.
Clarke does not teach a specific embodiment wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Clarke’s vicinal epoxide containing compound that is a compound or a mixture of compounds having a plurality of vicinal epoxide groups to be polyglycidyl ethers of polyhydric aliphatic compounds. The proposed modification would read on wherein the polyepoxide compound (B) is an aliphatic polyepoxide compound (B-1) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying mechanical properties of Clarke’s oxazolidinones because polyglycidyl ethers of polyhydric aliphatic compounds are more flexible than polyglycidyl ethers of polyhydric phenols or bisphenols, because polyglycidyl ethers of polyhydric phenols or bisphenols are more rigid than polyglycidyl ethers of polyhydric aliphatic compounds, and because Clarke teaches that the vicinal epoxide containing compound (1:7-8) is a compound or a mixture of compounds having a plurality of vicinal epoxide groups (5:1-3) and that suitable epoxide containing compounds include polyepoxides, such as the polyglycidyl ethers of polyhydric compounds such as, for example, polyhydric aliphatic compounds (1:46-54). Alternatively, one of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of vicinal epoxide that is suitable for Clarke’s process and/or because it would have been obvious to try with a reasonable expectation of success based on Clarke’s teachings that are recited above. Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Muller et al. (US 2017/0081462 A1, cited in IDS) as applied to claim 1, and further in view of Muller et al. (US 2017/0081459 A1).
Regarding claim 9, Muller 2017/0081462 A1 renders obvious the process according to claim 1 as explained above.
Muller 2017/0081462 A1 does not teach that the catalyst (C) is at least one compound selected from the claimed group. However, Muller 2017/0081459 A1 teaches a catalyst for the reaction of diisocyanates with diepoxides comprising at least one anionic moiety selected from CO32- and NO3- and at least one cationic moiety of formula [0082]
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[0072], wherein M is phosphorous, and (R1), (R2), (R3), and (R4) are all phenyl [0082], wherein the reaction optionally produces polyoxazolidinone compounds [0010], wherein an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0108], wherein the oligomeric or polymeric oxazolidinone compound optionally comprises at least two terminal isocyanate groups [0113]. Muller 2017/0081462 A1 and Muller 2017/0081459 A1 are analogous art because both references are in the same field of endeavor of a process for producing an optionally isocyanate-terminated polyoxazolidinone composition. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Muller 2017/0081459 A1’s catalyst comprising at least one anionic moiety selected from CO32- and NO3- and at least one cationic moiety of formula
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, wherein M is phosphorous, and (R1), (R2), (R3), and (R4) are all phenyl, to substitute for at least a fraction of Muller 2017/0081462 A1’s catalyst in Muller 2017/0081462 A1’s production of polymeric oxazolidinone compounds. The proposed modification would read on wherein the catalyst (C) is at least one compound selected from tetraphenylphosphonium nitrate, and tetraphenylphosphonium carbonate as claimed. One of ordinary skill in the art would have been motivated to do so because Muller 2017/0081459 A1 teaches that the catalyst comprising at least one anionic moiety selected from CO32- and NO3- and at least one cationic moiety of formula [0082]
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[0072], wherein M is phosphorous, and (R1), (R2), (R3), and (R4) are all phenyl, is beneficial for being a catalyst for the reaction of diisocyanates with diepoxides [0082], which would have been desirable for the catalyst in Muller 2017/0081462 A1’s production of polymeric oxazolidinone compounds, and which would have been beneficial for modifying catalysis properties in Muller 2017/0081462 A1’s production of polymeric oxazolidinone compounds because Muller 2017/0081462 A1 teaches that the catalyst is for production of polymeric oxazolidinone compounds by reacting an isocyanate compound with an epoxide compound in the presence of the catalyst system [0009], and that the catalyst is represented by the general formula
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wherein M is phosphorous or antimony, (R1), (R2), (R3), (R4) are independently of one another selected from the group comprising linear or branched alkyl groups containing 1 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents, cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents, C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, optionally substituted with heteroatoms and/or heteroatom containing substituents and aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms and/or heteroatom containing substituents and/or heteroatoms, whereas (R4) is different from (R1), (R2), and (R3) and is selected from the group comprising branched alkyl groups containing 3 to 22 carbon atoms, C1 to C3 alkyl-bridged cycloaliphatic groups containing 3 to 22 carbon atoms, and aryl groups containing 6 to 18 carbon atoms, optionally substituted with one or more alkyl groups containing 1 to 10 carbon atoms, and/or heteroatom containing substituents and/or heteroatoms, whereas (R1), (R2) are aryl groups containing 6 to 18 carbon atoms, Y is a halide, carbonate, nitrate, sulphate, or phosphate anion, and n is an integer of 1, 2, or 3 [0012].
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Clarke (US 3,687,897) as applied to claim 1, and further in view of Muller et al. (US 2017/0081459 A1).
Regarding claim 9, Clarke renders obvious the process according to claim 1 as explained above.
Clarke does not teach that the catalyst (C) is at least one compound selected from the claimed group. However, Muller 2017/0081459 A1 teaches a catalyst for the reaction of diisocyanates with diepoxides comprising at least one anionic moiety selected from CO32- and NO3- and at least one cationic moiety of formula [0082]
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[0072], wherein M is phosphorous, and (R1), (R2), (R3), and (R4) are all phenyl [0082], wherein the reaction optionally produces polyoxazolidinone compounds [0010], wherein an isocyanate terminated oligomer is obtained when the diisocyanate is employed in excess [0108], wherein the oligomeric or polymeric oxazolidinone compound optionally comprises at least two terminal isocyanate groups [0113]. Clarke and Muller are analogous art because both references are in the same field of endeavor of a process for producing an optionally isocyanate-terminated polyoxazolidinone composition. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Muller’s catalyst comprising at least one anionic moiety selected from CO32- and NO3- and at least one cationic moiety of formula
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, wherein M is phosphorous, and (R1), (R2), (R3), and (R4) are all phenyl, to substitute for at least a fraction of Clarke’s phosphonium catalyst in Clarke’s process for the preparation of oxazolidinones. The proposed modification would read on wherein the catalyst (C) is at least one compound selected from tetraphenylphosphonium nitrate, and tetraphenylphosphonium carbonate as claimed. One of ordinary skill in the art would have been motivated to do so because Muller teaches that the catalyst comprising at least one anionic moiety selected from CO32- and NO3- and at least one cationic moiety of formula [0082]
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[0072], wherein M is phosphorous, and (R1), (R2), (R3), and (R4) are all phenyl, is beneficial for being a catalyst for the reaction of diisocyanates with diepoxides [0082], which would have been desirable for the phosphonium catalyst in Clarke’s process for the preparation of oxazolidinones, and which would have been beneficial for modifying catalysis properties in Clarke’s process for the preparation of oxazolidinones because Clarke teaches that the phosphonium catalyst is for a process for the preparation of oxazolidinones which comprises reacting a vicinal epoxide containing compound with an organic isocyanate compound in the presence of the phosphonium catalyst (1:7-18), wherein suitable phosphonium catalysts include methyl tributyl phosphonium iodide, ethyltributyl phosphonium iodide, propyl tributyl phosphonium iodide, tetrabutyl phosphonium bromide, tetrabutyl phosphonium iodide, tetrabutyl phosphonium chloride, tetramethyl phosphonium bromide, tetramethyl phosphonium iodide, tetramethyl phosphonium chloride, ethyltricyclohexylphosphonium bromide, phenyltributylphosphonium iodide, methyltrioctylphosphonium dimethylphosphate, and tetra(3,3-dimethylbutyl)phosphonium chloride (5:47-59).
Correspondence
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/DAVID T KARST/ Primary Examiner, Art Unit 1767
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