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 .
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on January 22, 2026 has been entered.
Claims 1-12 are pending as amended on January 22, 2026. Support for amended claim 1 is found in original claim 1. Claims 2-10 stand withdrawn from consideration. Claim 12 is withdrawn from consideration because it has been amended from a product to a method and now belongs with the method group (claims 2-10).
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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.
Claim Rejections - 35 USC § 103
Claims 1 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Fuller (US 2448585, cited with 10/23/2025 Office action) in view of Yu (Competition and miscibility of isodimorphism and their effects on band spherulites and mechanical properties of poly(butylene succinate-co-cis-butene succinate) unsaturated aliphatic copolyesters, Polymer, 2018, 150, 52-63; cited with 10/23/2025 Office action) and evidenced by Nishiwaki (High-molecular-weight poly(1,2-propylene succinate): a soft biobased polyester applicable as an effective modifier of poly(L-lactide), Polymer Chemistry, 2018, 56, 1795-1805; cited with 10/23/2025 Office action).
Fuller teaches partially unsaturated polyesters (Fuller, col. 4, line 14). The polyesters are capable of being cured to synthetic rubbers (Fuller, col. 1, lines 1-3).
Fuller teaches that good rubbers can only be obtained from polyesters which are essentially non-crystalline at room temperatures (Fuller, col. 6, lines 44-46) and teaches that certain ingredients lead to polyesters which are incapable of crystallization (Fuller, col. 6, lines 73-74). Therefore, it would have been obvious to one of ordinary skill to select ingredients that produce a polyester incapable of crystallization and reading on a polyester without crystallization and melting. Fuller further teaches that isopropylene glycol forms non-crystalline polyesters with polymethylene di-carboxylic acids between succinic acid and sebacic acid (Fuller, col. 7, lines 35-40). Because Fuller teaches that crystallization tendencies increase as the length of the polymethylene chain increases (Fuller, col. 7, lines 24-28), one would be motivated to select succinic acid in order to decrease crystallization tendencies.
Fuller teaches that unsaturation can be introduced by unsaturated dicarboxylic acids, such as maleic and fumaric acids, and that unsaturated glycols are more difficult to obtain (Fuller, col. 4, lines 16-23). Fuller does not teach introducing unsaturation with butenediol.
However, Yu teaches that unsaturated diacids, including fumaric acid and maleic acid, have disadvantages (Yu, page 52, right col.). Yu teaches that uncrosslinked and linear unsaturated polyester is hard to obtain under conventional polycondensation conditions due to the highly reactive conjugated double bond (Yu, page 52, right col.). Yu further teaches that cis-2-butene-1,4-diol can be incorporated into copolyesters without isomerization or crosslinking due to the high chemical stability of the unconjugated cis-double bond (Yu, abstract). In addition, Yu teaches that cis-2-butene-1,4-diol is a rather inexpensive commercial unsaturated diol widely used in the biomedical fields (Yu, page 53, left col., lines 6-8).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have introduced unsaturation into the polyester of Fuller using the cis-2-butene-1,4-diol of Yu instead of the unsaturated dicarboxylic acid of Yu in order to reduce crosslinking during polyester synthesis and because Yu teaches that cis-2-butene-1,4-diol is inexpensive and widely available.
A polyester derived from cis-2-butene-1,4-diol, isopropylene glycol, and succinic acid reads on the following general formula,
PNG
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383
541
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Greyscale
wherein structural units derived from isopropylene glycol and succinic acid correspond to the “a” structural units and structural units derived from cis-2-butene-1,4-diol and succinic acid correspond to the “e” structural units. All other structural units have a degree of polymerization of 0.
In the structural formula above, Rm1 is a branched chain alkyl group wherein m1 represents the number of carbon atoms and m1=3 (residue derived from isopropylene glycol). Rn1 is an unbranched chain alkyl wherein n1 represents the number of carbon atoms and n1=2 (residue derived from succinic acid). Because structural units derived from isopropylene glycol and succinic acid correspond to the “a” structural unit, a, c, m and o are not 0 at the same time. Similarly, because structural units derived from cis-2-butene-1,4-diol and succinic acid correspond to the “e” structural units, e and k are not 0 at the same time.
While Fuller does not explicitly teach a glass transition temperature, Fuller describes the polyesters as non-crystalline, plastic gums at room temperature (Fuller, col. 1, lines 8-12) that are extremely viscous liquids at room temperature and have a consistency somewhat similar to that of milled crepe rubber (Fuller, col. 1, lines 39-43). Based on this description, the glass transition of the polyester would necessarily be lower than room temperature.
Nishiwaki provides evidentiary support of this position. Nishiwaki teaches poly(1,2-propylene succinate) referred to by Nishiwaki as PPS (Nishiwaki, abstract). Nishiwaki teaches that the PPS polymers can be applicable as elastomeric or flexible plastic modifiers (Nishiwaki, Abstract). The PPS samples prepared by Nishiwaki showed glass transitions in the range of -8 to -5 °C without crystallization behavior because of the complete amorphous nature (Nishiwaki, page 1802, lines 13-15). Nishiwaki therefore demonstrates a copolyester of isopropylene glycol and succinic acid exhibiting a glass transition temperature less than the room temperature without crystallization and melting.
Nishiwaki differs from modified Fuller in that the copolyester of modified Fuller comprises residues derived from cis-2-butene-1,4-diol. However, Fuller teaches that the greater the number of glycols and the greater the number of dicarboxylic acids used in preparing the polyester, the less will be the tendency to crystallize (Fuller, col. 8, lines 1-5) because the degree of order influences crystallinity (Fuller, col. 7, lines 70-73). Fuller also teaches that unsaturated monomers are used in such small concentrations that their effect on crystallinity is not great (Fuller, col. 7, 48-54). Therefore, one would not expect the addition of a small amount of cis-2-butene-1,4-diol to cause a copolyester of isopropylene glycol and succinic acid to crystallize. It is therefore reasonable to expect the copolyester isopropylene glycol, succinic acid, and cis-2-butene-1,4-diol to exhibit a glass transition temperature less than the room temperature without crystallization and melting.
While not explicitly an elastomer, the butenediol-based polyester of modified Fuller contains all of the claimed elements and would be expected to be capable of functioning as an elastomer.
Response to Arguments
Applicant’s arguments filed January 22, 2026 have been fully considered.
Applicant argues (pages 8-9) that modified Fuller does not teach or suggest a polyester where m1 and m2 are different and Rm1 and Rm2 are different to each other. In particular, Applicant argues that Fuller teaches away from m1 and m3 are different because Fuller discloses that partially replacing isopropylene glycol with other glycol excessively changes the crystallization behavior or the polyester. Applicant points to col. 7, lines 35-47 where Fuller teaches that with isopropylene sebacate, no more than about 30% of ethylene glycol can be substituted for the isopropylene glycol without inducing excessive crystallization. Fuller further teaches that isopropylene succinate does not become excessively crystalline when as much as 50-60% of the isopropylene glycol is replaced by ethylene glycol. This suggests that addition of ethylene glycol changes the crystallization behavior at lower contents when the diacid is sebacic acid (n1=10) than when the diacid is succinic acid (n1=2). It is noted that the features upon which applicant relies (i.e., m1 and m2 are different and Rm1 and Rm2 are different where both are present in the polyester) is not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). In this case, claim 1 as amended does not require repeating units derived from both m1 and m2 because up to 3 of a, c, m, and o can be 0 and either of e and k can be 0. In addition, Fuller does not teach away from all combinations of diols. Fuller teaches that the greater the number of glycols and the greater the number of dicaboxylic acids used the less will be the tendency to crystallize (col. 8, lines 1-5). Fuller also teaches that when the molecular structure departs from straight chain polymethylene arrangements, such as through the introduction of side chain substituents, hetero-atoms, or unsaturated carbon-to-carbon bonds, the polyesters become less crystalline (col. 7, lines 11-15). These statements are more general than the specific examples of copolymers of ethylene glycol, isopropylene glycol, and sebacic or succinic acid pointed to by Applicant and provide direction to one of ordinary skill of means to reduce or avoid crystallinity while utilizing multiple diols. In particular, the teaching that the greater the numbers of glycols used the less will be the tendency to crystallize does not teach away from including multiple diols of different number of carbon atoms (col. 8, lines 1-8).
Applicant further argues (pages 9-10) that none of the cited references disclose the range of 2≤m1≤14, 2≤m2≤14 and 2≤n1≤12, 2≤n2≤12 as recited in claim 1. Applicant can rebut a presumption of obviousness based on a claimed invention that falls within a prior art range by showing "(1) [t]hat the prior art taught away from the claimed invention...or (2) that there are new and unexpected results relative to the prior art." Iron Grip Barbell Co., Inc. v. USA Sports, Inc., 392 F.3d 1317, 1322, 73 USPQ2d 1225, 1228 (Fed. Cir. 2004). See MPEP 2144.III.B. As evidence, Applicant points to Fuller’s teaching of crystallizing examples based on decamethylene glycol or sebacic acid. This argument is not persuasive because the rejection relies upon a copolymer of isopropylene glycol, succinic acid, and cis-2-butene-1,4-diol rather than a copolymer comprising either or both of decamethylene glycol and sebacic acid and Fuller teaches differences in crystallinity for polyesters derived from these monomers. Decamethylene glycol (m1=10) and sebacic acid (n1=10) have longer polymethylene chains than isopropylene glycol (m1=3) and succinic acid (n1=2) and Fuller teaches that the crystallizing tendencies of the polyester increase as the length of the polymethylene chain increases (col. 7, lines 25-28). Fuller also teaches that isopropylene glycol forms non-crystalline polymers with succinic acid (col. 7, lines 35-39) and that unsaturated monomers are used in such small concentrations that their effect on crystallinity is not great (Fuller, col. 7, 48-54). Therefore, one would not expect the addition of a small amount of cis-2-butene-1,4-diol to cause a copolyester of isopropylene glycol and succinic acid to crystallize. Applicant’s argument would be persuasive if m1 or n1 were limited to 10 or greater because the examples pointed to by Applicant demonstrate crystallization in these cases.
Applicant argues (pages 10-11) that one of ordinary skill would not have been motivated to combined Fuller and Yu because one would not have had a reasonable expectation of introducing unsaturation into the polyester of Fuller using cis-2-butene-1,4-diol without changing the crystal structure and thermal behavior of the polyester of Fuller in view of Yu’s teachings. Evidence showing there was no reasonable expectation of success may support a conclusion of nonobviousness. In re Rinehart, 531 F.2d 1048, 189 USPQ 143 (CCPA 1976). See MPEP 2143.02.II. As evidence, Applicant points to Yu's teachings that molecular conformation and polymer chain packing of unsaturated copolyesters are poorly understood (Yu, page 53, col. 1, lines 11-24). This teaching is summarized from references other than Yu in the introduction of Yu and Applicant has not given enough information to know if this teaching is relevant to Fuller's polyesters. The rejection above relies on Yu to motivate modifying Fuller by using cis-2-butene-1,4-diol instead of an unsaturated dicarboxylic acid in order to reduce crosslinking during polyester synthesis. The resulting copolyester is a copolymer of cis-2-butene-1,4-diol, isopropylene glycol, and succinic acid whereas the copolyester of Yu is a copolymer of cis-2-butene-1,4-diol,1,4-butanediol, and succinic acid (Yu, Scheme 1). Because the copolyester of Yu is based on a different combination of monomers than modified Fuller, Yu's teachings on crystallinity would not be expected to be representative of modified Fuller. It is noted that the advisory action sentence quoted by Applicant contained a typographical error. The phrase “Fuller's teachings on crystallinity would not be expected to be representative of modified Fuller” was intended to read “Yu's teachings on crystallinity would not be expected to be representative of modified Fuller.” In addition, Fuller teaches that unsaturated monomers are used in such small concentrations that their effect on crystallinity is not great (Fuller, col. 7, 48-54). Based on the teachings of Fuller one would have had a reasonable expectation of successfully producing polyesters that are incapable of crystallization, as desired by Fuller (Fuller, col. 6, lines 44-46 and col. 6, lines 73-74).
Conclusion
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766