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 .
Claims 1, 3-4, and 6-9 are pending as amended on December 12, 2025. Support for amended claim 1 is found in claim 2. Claims 2 and 10-16 are cancelled.
The new grounds of rejection set forth below were solely modified to reflect the incorporation of claim 2 into amended claim 1. Therefore, this action is properly made final.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in the action can be found in a prior Office action.
Response to Arguments
Applicant’s arguments filed December 12, 2025 have been fully considered.
Applicant’s arguments, see page 5, with respect to the rejection under 35 U.S.C. 102 over Rehor (A new living emulsion polymerization mechanism: episulfide anionic polymerization, Macromolecules, 2002 (35) 8688-8693) are persuasive. Claim 1 has been amended to require that the polymerization is performed in an absence of a solvent. Rehor utilizes a solvent and does not suggest that the polymerization could be performed without a solvent. The rejections of claims 1, 4, and 6-9 over Rehor have been withdrawn.
Applicant’s arguments, see pages 5-7, with respect to the rejection under 35 U.S.C. 103 over Oswald (US 4,163,832) in view of Wragg (GB 1,193,335) and PubChem (1,1,3,3-Tetramethylguanidine. https://pubchem.ncbi.nlm.nih.gov/compound/66460. Accessed 4 Aug. 2025) are not persuasive for the reasons described below.
Applicant argues (page 7-8) that Oswald does not teach that a base whose conjugated acid has a dissociation constant (pKa) of 12 or greater would result in a process with improved features and therefore one would not be motivated to choose an amine compound that is not disclosed by Oswald and has a higher pKa than those listed by Oswald. The MPEP section 2144, subsection IV states, “The reason or motivation to modify the reference may often suggest what the inventor has done, but for a different purpose or to solve a different problem. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by applicant. See, e.g., In re Kahn, 441 F.3d 977, 987, 78 USPQ2d 1329, 1336 (Fed. Cir. 2006).” Oswald does not need to suggest the same motivation for modifying the catalyst as the instant application for the modification to be obvious. In this case, Oswald teaches amine catalysts such as tetramethylethylenediamine and pentamethyldiethylenetriamine. Like Oswald, Wragg teaches tetramethylethylenediamine and pentamethyldiethylenetriamine as catalysts for the polymerization of an alicyclic episulfide (cyclohexadiene diepisulphide). Wragg also teaches using tetramethyl guanidine as a catalyst for the same polymerization. Therefore, one of ordinary skill would have recognized that tetramethyl guanidine could be used as an alternative to the tetramethylethylenediamine and pentamethyldiethylenetriamine catalysts taught by Oswald. Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR International Co. v. Teleflex Inc., 550 U.S. 398 (2007). MPEP § 2143, rationale (B). Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have substituted the tertiary amine, such as tetramethylethylenediamine and pentamethyldiethylenetriamine, of Oswald for the tetramethyl guanidine of Wragg. One would have had a reasonable expectation of successfully polymerizing cyclohexene sulfide because Wragg teaches tetramethyl guanidine as a catalyst for the polymerization of an alicyclic episulfide, tetramethyl guanidine is a tertiary amine, as required by Oswald, and the tertiary amines taught by Oswald include tertiary amines that read on the polyamine taught by Wragg (tetramethylethylenediamine and pentamethyldiethylenetriamine).
Applicant argues (page 8, paragraph 2) that one would not have selected tetramethylethylenediamine or pentamethyldiethylenetriamine from the polyamines taught by Oswald without hindsight reconstruction because Oswald teaches that trimethylamine is most favorable. It must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). In addition, all disclosures “including unpreferred embodiments” must be considered. In re Lamberti 192 USPQ 278, 280 (CCPA 1976) citing In re Mills 176 USPQ 196 (CCPA 1972). Because Oswald teaches tetramethylethylenediamine and pentamethyldiethylenetriamine as amine catalysts (col. 10, lines 1-17), one of ordinary skill would have expected these catalysts to be sufficient for catalyzing the polymerization even though Oswald exemplifies trimethylamine. Therefore, one of ordinary skill could have selected tetramethylethylenediamine or pentamethyldiethylenetriamine based solely on the teaching of Oswald and without hindsight reconstruction.
Applicant argues (page 8, paragraph 3) that the present invention does not involve simple substitution of equivalent chemicals. The rejection is not based on equivalent chemicals. Rather, the rejection is based on substituting one known tertiary amine catalyst for another known tertiary amine catalyst to obtain the predictable result of catalyzing the polymerization of an alicyclic episulfide. Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR International Co. v. Teleflex Inc., 550 U.S. 398 (2007). MPEP § 2143, rationale (B).
Applicant argues (page 8, paragraph 3) that the present invention produces unexpected results. To the extent that this argument may be construed as an allegation of unexpected results, the evidence pointed to by Applicant does not demonstrate the alleged unexpected result in a manner that is commensurate in scope with the claimed invention. MPEP 716.02(b) states that appellants have the burden of explaining the data in any declaration they proffer as evidence of non-obviousness. Ex parte Ishizaka, 24 USPQ2d 1621, 1624 (Bd. Pat. App. & Inter. 1992). Applicant has not sufficiently explained the data in examples 1-16 and comparative examples 1-2 at least because Applicant has not described how the data demonstrates unexpected results and Applicant has not compared the data to the closest prior art. Additionally, evidence of nonobviousness must be commensurate in scope with the claims for which the evidence is offered to support. See MPEP 716.02(d). For example, claim 1 encompasses alicyclic episulfide compounds and bases not utilized in the instant examples.
Claim Rejections - 35 USC § 103
Claims 1, 3-4 and 6-9 are rejected under 35 U.S.C. 103 as being unpatentable over Oswald (US 4,163,832, Cite No. 1 on 4/17/2024 IDS) in view of Wragg (GB 1,193,335, Cite No. 2 on 4/17/2024 IDS) and PubChem (1,1,3,3-Tetramethylguanidine. https://pubchem.ncbi.nlm.nih.gov/compound/66460. Accessed 4 Aug. 2025.).
Regarding claims 1, 4, and 9, Oswald teaches a method for producing a polythioether compound, the method comprising performing a ring-opening polymerization of an episulfide compound in a presence of a base (a selective anionic ring opening process which comprises reacting episulfides with thiols in the presence of tertiary amines, Oswald, column 3, lines 24-26). Oswald further teaches wherein the ring-opening polymerization is performed in an absence of a solvent (solvents are not necessary for the reactions, Oswald, column 12, lines 27-28).
As an episulfide compound, Oswald teaches cyclohexene sulfide (Oswald, column 4, lines 30-33), reading on an alicyclic episulfide (claim 1) including a compound represented by Formula (I) where ring A represents an alicyclic ring having 6 carbons and r represents a natural number (0), as recited in claim 9.
Oswald teaches that the polythioether compounds have 3 to 20,000 recurring alkylene sulfide groups (Oswald, claim 1), corresponding to a degree of polymerization of about 3 to 20,000. Cyclohexene sulfide has a molecular weight of 114 g/mol, so a degree of polymerization of 3 to 20,000 corresponds to a molecular weight range of approximately 342 g/mol to 2,280,000 g/mol. This range overlaps with the range of wherein a number average molecular weight of the polythioether compound is from 500 to 50000 recited in claim 1. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Oswald teaches the use of tertiary amines (Oswald, column 3, lines 24-35), but does not teach wherein the base is a base whose conjugated acid has an acid dissociation constant (pKa) of 12 or greater.
However, prior to the effective filing date of the claimed invention, bases whose conjugated acid has a pKa greater than 12 were known to be useful in polythioether synthesis, as evidenced by Wragg. Wragg teaches the polymerization of episulphides, including cyclohexadiene diepisulphide (Wragg, column 2, lines 33-44). Wragg teaches that the polymerization is performed in the presence of a polyamine (Wragg, column 1, lines 12-15). Suitable polyamines have the formula
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Wherein R1, R2, R4, R6, R7, and R9 each represents a hydrogen atom or an alkyl, cycloalkyl, aralkyl, or aryl group, or wherein R1 and R8 bridge together to form a hydrocarbon bridge and/or R2 and R9 together form a hydrocarbon bridge, provided that at least one of R1, R2, R4, R6, R8, and R9 is not a hydrogen atom and wherein R3, R5, and R7 each represents a divalent organic radical selected from acyclic and cyclic aliphatic hydrocarbon, aromatic hydrocarbon, and aliphatic/aromatic hydrocarbon groups and substituted hydrocarbon groups in which the substituents do not reduce the basicity of the amino groups and wherein x, y, and n each represents zero or an integer (Wragg, column 1 line 64 to column 2 line 6). One exemplified polyamine taught by Wragg is tetramethyl guanidine (Wragg, column 2, line 15). Polyamines taught by Oswald that also read on the formula of Wragg include tetramethylethylenediamine (n=0; R7 = ethyl, and R1, R2, R8, and R9=methyl) and pentamethyldiethylenetriamine (n and x=1; R7 and R3=ethyl; y=1 and R1, R2, R8, and R9=methyl) (Oswald, column 10, lines 1-17). Given the disclosure of Wragg, one of ordinary skill in the art would have recognized that tetramethyl guanidine was known in the art as an alternative tertiary amine to tetramethylethylenediamine and pentamethyldiethylenetriamine in the production of polythioether compounds derived from alicyclic episulfides.
Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR International Co. v. Teleflex Inc., 550 U.S. 398 (2007). MPEP § 2143, rationale (B). Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have substituted the tertiary amine of Oswald for the tetramethyl guanidine of Wragg. One would have had a reasonable expectation of successfully polymerizing cyclohexene sulfide because Wragg teaches tetramethyl guanidine as a catalyst for the polymerization of an alicyclic episulfide (cyclohexadiene diepisulphide). In addition, tetramethyl guanidine is a tertiary amine, as required by Oswald, and the tertiary amines taught by Oswald include tertiary amines that read on the polyamine taught by Wragg (tetramethylethylenediamine and pentamethyldiethylenetriamine).
Tetramethyl guanidine as the tertiary amine component reads on wherein the base in an amine compound (claim 4) and wherein the base is a base whose conjugated acid has an acid dissociation constant (pKa) of about 13.6 (PubChem, page 9, section 3.2.4), falling with the range of 12 or greater recited in claim 1.
Regarding claim 3, Oswald teaches the method for producing a polythioether compound according to claim 1 and further teaches that a preferable reaction temperature for the ring opening polymerization is in the range of 25° C to 40° C (Oswald, column 12, lines 9-16). A range of 25° C to 40° C overlaps with the claimed range of wherein the ring-opening polymerization is performed at a reaction temperature of 30°C or higher. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Regarding claims 6-8, Oswald teaches the method for producing a polythioether compound according to claim 1 and further teaches wherein the ring-opening polymerization further proceeds in a presence of a thiol compound (Oswald, column 3, lines 24-27), as recited in claim 6. Oswald further teaches wherein the thiol compound has two or more thiol groups in a molecule, as recited in claim 8 (aliphatic polythiols, e.g. dithiols are the preferred polythiols of this invention, Oswald, column 5, lines 12-13). Oswald teaches that the amine catalyst is used in an amount of about 0.1 to about 1 mole per mole of thiol reactant (Oswald, column 11, lines 56-60). For a thiol reactant that is a dithiol, this corresponds to the base being used in a proportion of about 0.05 to 0.5 equivalent per equivalent of thiol group in the thiol compound. This range falls within the range of 0.001 equivalent or greater and less than 1 equivalent per equivalent of thiol group contained in the thiol compound recited in claim 7.
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 nonprovisional extension fee (37 CFR 1.17(a)) 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.
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766