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 .
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, 2, 13, 14, 15, 18, 21, 28, 30, 33-46 are rejected 35 U.S.C. 103 as being unpatentable over Koenig (US5112932, herein Koenig).
Regarding Claims 1, 2, 14, 21, 28, 33, 34, 35, 36, 38, 39, Koenig teaches isocyanate modified epoxy resins (epoxy-terminated polyoxazolidones), which Koenig further notifies oxazolidone (commonly referred to in the past as "2-oxazolidinone") [C1; L6-14], wherein, the polyoxazolidinone is generally synonymous with poly-2-oxazolidinone, and Poly-2-oxazolidones consist of recurring 2-oxazolidinone units. Koenig further teaches the epoxy-terminated polyoxazolidone is formed by the preparation process comprises reacting a polyepoxide compound with a polyisocyanate compound in the presence of a catalyst [C4; L60-65], which indicates the copolymerization via polyepoxide compound react with a polyisocyanate compound, and forms epoxy-terminated polyoxazolidones.
Koenig teaches suitable polyisocyanates include 4,4'-methylene bis(phenylisocyanate) (MDI) [C6; L67] reads on the polyisocyanate compound with two isocyanate groups.
Koenig teaches polyepoxides having the following general formula [C6; L40-45]
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wherein R is substituted or unsubstituted aliphatic group and n has an average value of from greater than about 1 to less than about 5. [C6; L45-50], overlaps the claimed epoxy group number, and collectively read on both polyepoxide compound B and B-1.
It would have been obvious to someone of ordinary skill in the art before the effective filing date of the claimed invention to utilize the formula [C6; L40-45] as the polyepoxide selection guidance, with the R is substituted or unsubstituted aliphatic group and n has an average value of from greater than about 1 to less than about 5. [C6; L45-50], and apply these specific polyepoxides with the a) R is substituted or unsubstituted aliphatic group and b) n values as taught by Koenig, and apply into the process of preparing the isocyanate modified epoxy resins (epoxy-terminated polyoxazolidones). Doing so would further allow the copolymerization within specific range of from about 110° C. to about 200° C [C5; L15] which affect the higher conversion of the isocyanate groups to oxazolidone rings (up to about 100 percent conversion) is achieved [C5; L24-26]; which further lead to the excellent physical and mechanical properties; desired glass transition temperature; chemical resistivity [C10; L31-40], as taught by Koenig.
Koenig teaches tetraphenylphosphonium bromide as catalyst [C25; L40], abbreviated as Ph4PBr, Koenig teaches 1.89 of tetraphenylphosphonium bromide react with 532 g of Epoxy Resin A; 64.7 g of Isocyanate A [C15; L5], wherein, the Epoxy Resin A stands for a diglycidyl ether of bisphenol A [C12; L44]; Isocyanate A stands for MDI [C13; L3], hence, the molar ratio between tetraphenylphosphonium bromide and diglycidyl ether of bisphenol A is (1.89/419.29) : (532/340.419)=0.0045/1.56=0.288 mole%, lies in the claimed range. In addition, the molar ratio between diglycidyl ether of bisphenol A and Isocyanate A (MDI) is (532/340.419): (64.7/250.25)=1.56/0.26=6:1, lies in the claimed ranges.
Koenig explicitly teaches the reaction of the polyepoxide compound and the polyisocyanate compound according to the process of the present invention is conducted neat, that is, in the absence of a solvent [C8; L13], which indicates the exclusion of solvent (D-1), additionally, the instant claim 2 further does not require the D-1, which is an optional ingredient used in the process.
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). See MPEP § 2144.05.
Regarding Claim 13, Koenig teaches the process for producing an epoxy-group terminated polyoxazolidinone as set forth in claim 1 above. Koenig teaches Epoxy Resin A, while stirring, the flask was heated to 90° C., 1.89 of tetraphenylphosphonium bromide was added to the flask and the resultant mixture heated to about 150° C. [C15; L5-10], indicates the mixing the polyepoxide compound (B) and at least part of the catalyst (C) forming a mixture hence match the step alpha); Koenig further teaches then, 64.7 g of Isocyanate A was placed in the addition funnel and added dropwise to the flask. The temperature of the reaction mixture was raised by exothermic reaction to about 195° C [C15; L10-14]; and after the end of addition of Isocyanate A, a sample was taken and analyzed [C15; L14-16], collectively indicate the addition of the polyisocyanate compound (A) to the mixture (alpha) at copolymerization conditions matches the step beta).
Regarding Claims 15, 30, 37, 40, Koenig teaches the process for producing an epoxy-group terminated polyoxazolidinone as set forth in claims 14, 28, 36, 39 above. Koenig teaches this product has an EEW (epoxy equivalent weights) of 234 [C15; L19], lies in the claimed range.
Claims 41-46 are rejected 35 U.S.C. 103 as being unpatentable over Koenig (US5112932, herein Koenig) as set forth in claim 1 above, in the view of Kaufman (EP0113575, herein Kaufman).
Regarding Claim 41, Koenig teaches the process for producing an epoxy-group terminated polyoxazolidinone as set forth in claim 1 above. Koenig does not explicitly teach the molar ratio of epoxy groups of the polyepoxide compound (B) to the isocyanate groups of the polyisocyanate compound (A) is from 2.6:1 to 5:1. However, Kaufman teaches diepoxide and diisocyanate reactants which provide a ratio of epoxide equivalents to isocyanate equivalents from 10:1 to 1.1:1 [0009], overlaps the claimed range. Koenig and Kaufman are both considered to be analogous to the claimed invention because they are reasonably pertinent to the problem faced by the inventor, that of the formation of epoxy-terminated polyoxazolidone via copolymerization process optimization. Therefore, it would have been obvious to someone of ordinary skill in the art before the effective filing date of the claimed invention to utilize the ratio of epoxide equivalents to isocyanate equivalents from 10:1 to 1.1:1 [0009] as taught by Kaufman, to optimize the amounts of polyepoxide compound and the polyisocyanate compound, and further apply into the copolymerization process. Doing so can optimize the copolymerization process by enable the reaction temperature from within 100°C to 180°C [0012] lead to such polyoxazolidone resins exhibit desirably higher glass transition temperatures with acceptably low melt viscosities [0013], and further lead to desired molecular weight and epoxy equivalent weight [0009].
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). See MPEP § 2144.05.
Regarding Claim 42, Koenig teaches isocyanate modified epoxy resins (epoxy-terminated polyoxazolidones), which Koenig further notifies oxazolidone (commonly referred to in the past as "2-oxazolidinone") [C1; L6-14], formed by the preparation process comprises reacting a polyepoxide compound with a polyisocyanate compound in the presence of a catalyst [C4; L60-65], which indicates the copolymerization via polyepoxide compound react with a polyisocyanate compound, and forms epoxy-terminated polyoxazolidones.
Regarding Claim 43, Koenig teaches this product has an EEW (epoxy equivalent weights) of 234 [C15; L19], lies in the claimed range.
Regarding Claim 44, Koenig teaches tetraphenylphosphonium bromide as catalyst [C25; L40], abbreviated as Ph4PBr.
Regarding Claim 45, Koenig teaches isocyanate modified epoxy resins (epoxy-terminated polyoxazolidones), which Koenig further notifies oxazolidone (commonly referred to in the past as "2-oxazolidinone") [C1; L6-14], formed by the preparation process comprises reacting a polyepoxide compound with a polyisocyanate compound in the presence of a catalyst [C4; L60-65], which indicates the copolymerization via polyepoxide compound react with a polyisocyanate compound, and forms epoxy-terminated polyoxazolidones.
Regarding Claim 46, Koenig teaches this product has an EEW (epoxy equivalent weights) of 234 [C15; L19], lies in the claimed range.
Response to Arguments
Applicant’s arguments with respect to claim(s) 1 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
The applicant's argument that “unexpected results” which also within the declaration under 37 CFR 1.132 filed 1/27/2026, are further not commensurate in scope with the claim 1, hence, insufficient to establish non-obviousness.
In this case, first, the newly cited reference_ Koenig explicitly teaches polyepoxides having the following general formula [C6; L40-45].
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wherein R is substituted or unsubstituted aliphatic group and n has an average value of from greater than about 1 to less than about 5. [C6; L45-50], indicates the selection of the aliphatic polyepoxide compound. Furthermore, Koenig explicitly teaches the tetraphenylphosphonium bromide as catalyst [C25; L40], abbreviated as Ph4PBr, collectively meet both the instant application and the declaration under 37 CFR 1.132 filed 1/27/2026.
Second, the claim 1 is open to optionally a solvent (D-1) with a boiling point higher than 170 0C at 1 bar absolute, which indicates the using of solvent (D-1) is not excluded. However, Examples 1, 3, 9, 12, 18, and Comp. examples 11, 13, 15-17, all use 0% solvent (D-1) as single value. Therefore, these examples are not commensurate in scope with the claims and cannot be relied upon to establish non-obviousness.
Furthermore, the claim 1 is open to wherein the molar ratio of the epoxy groups of the polyepoxide compound (B) to the isocyanate groups of the polyisocyanate compound (A) is from 2.6:1 to 7:1. However, Examples 1, 3, 9, 12, and Comp. examples 4, 7, 8, 11, 13-17 all use wherein the molar ratio of the epoxy groups of the polyepoxide compound (B) to the isocyanate groups of the polyisocyanate compound (A) 3.3:1 as single ratio value. Therefore, these examples are not commensurate in scope with the claims and cannot be relied upon to establish non-obviousness.
In addition, the claim 1 is open to polyisocyanate compound (A) with two or more isocyanate groups. However, Examples 1, 2, 3, 9, 18, and Comp. examples 4-8, 10, 11, 14-17 all use MDI (4,4′-Methylenebis(phenyl isocyanate)) with a single value of two isocyanate groups. Therefore, these examples are not commensurate in scope with the claims and cannot be relied upon to establish non-obviousness.
Whether unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. See MPEP 716.02(d).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any extension fee pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Zhen Liu whose telephone number is (703)756-4782. The examiner can normally be reached Monday-Friday 9:00 am - 5:00 pm.
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/Z.L./
Examiner, Art Unit 1767
/MARK EASHOO/Supervisory Patent Examiner, Art Unit 1767
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