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 Status
Claims 1-15 were filed 6/29/2023 and are pending.
Priority
The instant application was filed 6/29/2023 and claims the benefit of priority to:
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See filing receipt dated 6/20/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 1 is objected to because of the following informalities: in line 2, the indefinite article –an—should be inserted before the word “amine”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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.
Claim 8 is 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 8 recites “the method of claim 1, wherein the distillation column in the low boiling material-removing step is provided with an internal baffle to prevent the overheated inert gas from mixing into the bottom of the distillation column”. This limitation is indefinite because claim 1, from which claim 8 depends explicitly recites that “overheated inert gas is supplied to the bottom of the distillation column through the reboiler”. So, though an internal baffle is definite, it is not clear how it is required to be oriented with respect to the bottom of the column and the inlet for the overheated inert gas at the bottom of the column.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
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.
Claim(s) 1-11 and 13-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yamasaki (US 2019/0292304, published on 6/26/2019) in view of Osamu (US 3549504, published on 12/22/1970).
Applicant claims a method for preparing an isocyanate compound comprising
A reaction step of reacting a salt of an amine compound with phosgene in the presence of a solvent to obtain a reaction product containing an isocyanate compound;
A degassing step of removing a gas phase from the reaction product;
A desolvation step of removing a solvent from the reaction product from which the gas phase has been removed;
A low boiling material-removing step of removing low boiling materials from the reaction product from which the solvent has been removed, and
A high boiling material-removing step of removing high boiling materials from the reaction product from which the low boiling materials have been removed;
Wherein the low boiling material-removing step is progressed in a distillation column to which a reboiler is connected to the bottom of the column and overheated inert gas is supplied to the bottom of the distillation column through the reboiler.
Yamasaki teaches a process for producing xylylene diisocyanate comprising reacting an aliphatic xylylenediamine (XDA, o, m, and/or p-see claims 9-11 and 13) hydrochloride salt (HCl, claim 14) with phosgene (carbonyl chloride) in an inert solvent, including aromatic hydrocarbons and esters (claim 15) to produce the corresponding xylylene isocyanates. See [0052-0084-steps a and b] and the following Fig. 1:
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Thus, step A of Yamasaki corresponds to the formation of the XDA·HCl salt and step B corresponds to the instantly claimed “reaction” step. Yamasaki then teaches a step C comprising a degassing step (41) to remove a gas phase (45) from the product and a desolvation step (51) to remove the solvent (55) from the reaction product from which the gas phase has been removed (42). See [0085-0090]. Yamasaki teaches that the degassed and desolvated reaction mixture (52) is fed to a tar-removal unit (61) and then passed via line (63) to a low-boiling removal tower (71) to remove low boiling impurities (74) to produce reaction stream (76) from the bottom of the column in a step d. See [0091-0101]. Bottoms stream (76) is fed to rectification column (81), wherein high boiling impurities are removed vial line (86) from the bottom of the column and providing purified xylylene diisocyanate (XDI) distillate product from the top of the column via line (84). See [0102-0109]. Figure 1 is fully defined with respect to the process in [0110-0173]. Therefore, Yamasaki teaches all of the steps recited in instant claim 1. Yamasaki further teaches that the temperature of the mixture at any point in the process should not exceed 190°C to prevent by-product formation and optimal conversion, and preferably falls within the range of 110-180°C (claim 5). See [0071, 0096-0097, 0104-0105].
Further regarding the low boiling material-removing step in column (71), Yamasaki teaches that the column is equipped with a reboiler (78) to heat and re-circulate a portion of the bottoms product (76) back to the bottom of the column (71) via line (77). Yamasaki teaches that the reboiler (78) regulates the internal temperature of the low-boiling removal tower (71) and can use the “above-described” heat exchanger. See [0160-0162 and heat exchanger in 0139]. Yamasaki teaches that column (71) preferably has a column bottom temperature between 130 to 200°C, a column top temperature between 90-160°C and a column-top pressure between 0.05 – 3 kPa (0.375 – 22.5 torr). See [0096-0098].
Yamasaki does not explicitly teach that overheated (see p. 17, first paragraph of the specification as filed) inert gas is supplied to the bottom of the distillation column through the reboiler.
Osamu teaches a method for the purification of organic polyisocyanates, including xylylenediisocyanate, by fractional distillation in the presence of an inert gas or superheated vapor of an organic solvent. See abstract. In col. 1, lines 38-53, Osamu teaches: “An organic polyisocyanate, when produced by reacting the corresponding amine with phosgene, inevitably contains various byproducts having relatively low boiling points. This makes it necessary to submit the product mixture to a further purification process. Organic polyisocyanates, as is well known, have relatively high boiling points and are very unstable when heated. Heretofore, for the purpose of purifying the materials having high boiling point and which are susceptible to deterioration upon heating, a vacuum distillation method has usually been employed. However, in this method, the material to be purified is eventually subjected to a comparatively high temperature due to a remarkable rising of temperature necessarily caused around the bottom of distillation column by pressure drop. Therefore, organic polyisocyanates cannot be safely purified by this method.”
Osamu overcomes the issue by subjecting a mixture of an organic polyisocyanate and light (boiling) impurities to fractionation (distillation) by allowing the crude organic polyisocyanate to contact an inert gas in a fractionation column under such conditions that the pressure at the top of the fractionation column is lower than 200 mm Hg (torr) and the feed rate (C) of the inert gas satisfies equation (I). See col. 2, line 3 to col. 3, line 64. Figure 1 teaches an embodiment wherein an inert gas is used as the inert feed and Figure 2 teaches an embodiment wherein a superheated vapor of an organic solvent is used as the inert feed. See col. 2, lines 53-57.
Osamu teaches that the crude organic polyisocyanates may be treated by the present method in the form of the phosgenation products without any preparatory treatment, though removal of the high-boiling constituents is preferred. See col. 3, lines 15-21. The purification of XDI is exemplified in example 3 (Fig. 1) and in col. 8-14 (Fig. 2). Osamu teaches that the superheated solvent can comprise aliphatic hydrocarbons having 2 to 11 carbon atoms (claim 3). See col. 10, lines 18-40 and example D, including Table in col. 13-14. Osamu also teaches that the inert gas can be methane (CH4, a C1 hydrocarbon). See col. 3, lines 22-27. Osamu teaches that the superheated solvent/inert gas is heated to a temperature of between 100 to 210°C, depending on the polyisocyanate, with a temperature in the range of 100-170°C for XDI (claims 4-6). See claim 8; example D in col. 13-14; col. 3, lines 50-60; and col. 10, lines 48-53 including xylylenediisocyanate. The pressure of the bottom of the column (PB) is within the range of 5 to 200 mm Hg (torr), preferably 50 to 200 mmHg (torr), wherein both ranges overlap with the range of claim 6. See col. 2, lines 3-4 and col. 3, lines 65-67. Also see MPEP 2144.05. Osamu teaches that the reboiler is a jacked vessel type reboiler equipped with a gas feed (sparger) ring which is fed from a heater (claims 2 and 7). See example 1 (Fig. 1) and example A in col. 11 (Fig. 2). Osamu teaches that the fractionating (distillation) apparatus can include columns with internal trays (baffles) (claim 8). See col. 3, lines 28-35.
It would have been prima facie obvious to combine the teachings of Yamasaki and Osamu to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to feed an overheated inert gas stream to the reboiler in the process of Yamasaki because Osamu teaches that such a modification is known to prevent pressure drop during the distillation of the same polyisocyanate system (XDI) at similar temperatures and pressures. Therefore, including the overheated inert gas of Osamu in the process of Yamasaki will predictably increase the efficiency of the XDI production process by eliminating deleterious pressure drop in the low-boiling point removal distillation step. Also see MPEP 2143(I)(A).
Claim(s) 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yamasaki (US 20190292304, published on 6/26/2019) in view of Osamu (US 3549504, published on 12/22/1970), as applied to claims 1-11 and 13-15 above and further in view of Wang (“Facile Synthesis of Reductively Degradable Biopolymers Using Cystamine Diisocyanate as a Coupling Agent” Biomacromolecules, 2016, 17, p. 882).
The Applicant claims a method wherein the amine compound is a sulfur-containing aliphatic amine selected from those among claim 12. Neither Yamasaki nor Osamu explicitly teach or suggest the use of the claimed amines.
Wang is directed toward the synthesis of biopolymers using cystamine diisocyanate (CDI) as a coupling agent. See abstract. Wang teaches that CDI is obtained from the corresponding amine hydrochloride (CDH) with triphosgene (BTC):
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. See p. 885. CDH corresponds to the HCl salt of “bis(aminoethyl)disulfide”. Wang teaches that CDI provides facile access to reductively degradable biopolymers via condensation polymerization with various diols. See abstract.
It would have been prima facie obvious to combine the teachings of Yamasaki, Osamu, and Wang to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to employ bis(aminoethyl)disulfide as a reactant in the process of Yamasaki and Osamu because Wang teaches that the isocyanate derived therefrom (CDI) has utility in biopolymer formation and can be made by an analogous process. Therefore, replacing one known amine with another known amine that can produce a valuable polymerization intermediate in a known and predictable process is prima facie obvious. Also see MPEP 2143(I)(B).
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-11 and 13-15 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of co-pending U.S. App. No. 18/259792 (‘792) in view of Osamu (US 3549504, published on 12/22/1970).
The claims of ‘792 are directed toward the same process as that claimed, but does not teach that the low boiling material-removing step is progressed in a distillation column to which reboiler is connected to the bottom of the column, and overheated inert gas is supplied to the bottom of the distillation column through the reboiler.
The teachings of Osamu were discussed in detail in the above rejections and is incorporated by reference herein.
It would have been prima facie obvious to combine the teachings of the claims of ‘792 and Osamu to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to feed an overheated inert gas stream to the reboiler in the process of ‘792 because Osamu teaches that such a modification is known to prevent pressure drop during the distillation of the same polyisocyanate system (XDI) at similar temperatures and pressures. Therefore, including the overheated inert gas of Osamu in the process of ‘792 will predictably increase the efficiency of the XDI production process by eliminating deleterious pressure drop in the low-boiling point removal distillation step. Also see MPEP 2143(I)(A).
Claims 12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of co-pending U.S. App. No. 18/259792 (‘792) in view of Osamu (US 3549504, published on 12/22/1970), as applied to claims 1-11 and 13-15,and further in view of Wang (“Facile Synthesis of Reductively Degradable Biopolymers Using Cystamine Diisocyanate as a Coupling Agent” Biomacromolecules, 2016, 17, p. 882).
The claims of ‘792 and Osamu are silent regarding the use of a sulfur-containing aliphatic amine selected from those among claim 12. The teachings of Wang were discussed in detail in the above rejections and is incorporated by reference herein.
It would have been prima facie obvious to combine the teachings of the claims of ‘792, Osamu, and Wang to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to employ bis(aminoethyl)disulfide as a reactant in the process of ‘792 and Osamu because Wang teaches that the isocyanate derived therefrom (CDI) has utility in biopolymer formation and can be made by an analogous process. Therefore, replacing one known amine with another known amine that can produce a valuable polymerization intermediate in a known and predictable process is prima facie obvious. Also see MPEP 2143(I)(B).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692