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 1-15 are pending as amended on June 30, 2026. Claims 2-10 and 12 stand withdrawn from consideration. Support for amended claim 1 is found in original claim 1 and [0047]. New claims 13-15 are supported by [0051], [0069], and [0075].
The new grounds of rejection set forth below were necessitated by new claims 13-15 and the amendment to claim 1 requiring that at least one of a, c, and e is greater than 0, at least one of k, m, and o is greater than 0, and n1 and n2 are different. 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Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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.
Claim Rejections - 35 USC § 103
Claims 1, 11, and 13-15 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).
Regarding claim 1, Fuller teaches partially unsaturated polyesters (col. 4, line 14) capable of being cured to synthetic rubbers (col. 1, lines 1-3). Fuller teaches that good rubbers can only be obtained from polyesters which are essentially non-crystalline at room temperatures (col. 6, lines 44-46) and that certain ingredients lead to polyesters that are incapable of crystallization (col. 6, lines 73-74). Fuller further describes the polyesters as non-crystalline plastic gums and extremely viscous liquids at room temperature (col. 1, lines 8-12 and 39-43). Based on this description, Fuller’s copolyester is amorphous and has a glass transition temperature (Tg) lower than room temperature without crystallization and melting. Therefore, it would have been obvious to one of ordinary skill to select ingredients that produce a polyester with an amorphous structure and a Tg lower than room temperature without crystallization and melting.
Fuller teaches that isopropylene glycol forms non-crystalline polyesters with polymethylene dicarboxylic acids between succinic acid and sebacic acid (col. 7, lines 35-40). Fuller teaches that crystallization tendencies increase as the length of the polymethylene chain increases (col. 7, lines 24-28) and that the greater the number of dicarboxylic acids used in preparing the polyester, the less will be the tendency to crystallize (col. 8, lines 1-5). Fuller also teaches that isopropylene glycol forms a non-crystalline polyester with polymethylene dicarboxylic acids between succinic acid and sebacic acid (col. 7, lines 35-40), but that substituting some isopropylene glycol for ethylene glycol impacts crystallinity. In particular, when the dicarboxylic acid is succinic acid (n2=2), 50-60% of the isopropylene glycol can be replaced with ethylene glycol without excessive crystallization, but when the dicarboxylic acid is sebacic acid (n2=10), only up to 30% of the isopropylene glycol can be replaced with ethylene glycol without excessive crystallization (col. 7, lines 40-47). Based on these teachings, one of ordinary skill would have understood that using multiple dicarboxylic acids and shorter dicarboxylic acids decreases the tendency to crystallize and that the relative amounts each monomer influence crystallinity.
Therefore, it would have been obvious to one of ordinary skill to use isopropylene glycol as the diol component because Fuller demonstrates non-crystalline polyesters derived from isopropylene glycol. It would have further been obvious to include succinic acid in the dicarboxylic acid component in order to avoid crystallization because succinic acid is the shortest dicarboxylic acid taught by Fuller. Because Fuller teaches that using multiple dicarboxylic acids decreases the tendency to crystallize, it would have been obvious to include a second polymethylene dicarboxylic acid between glutaric acid and sebacic acid (glutaric acid has one more methylene group than succinic acid) in an amount that avoids crystallinity. Taken together, it would have been obvious to one of ordinary skill to have selected a combination of isopropylene glycol, succinic acid, and a polymethylene dicarboxylic acid between glutaric acid and sebacic acid in order to obtain a copolyester that does not crystallize.
Fuller teaches introducing unsaturation with unsaturated dicarboxylic acids, such as maleic and fumaric acids, and that unsaturated glycols are more difficult to obtain (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 polyesters are 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 Fuller 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, succinic acid, and a polymethylene dicarboxylic acid between glutaric acid and sebacic acid (second dicarboxylic acid) reads on the following general formula:
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where structural units derived from isopropylene glycol and succinic acid correspond to “a” units, structural units derived from isopropylene glycol and the second dicarboxylic acid correspond to “o” units, structural units derived from cis-2-butene-1,4-diol and succinic acid correspond to “e” units, and structural units derived from cis-2-butene-1,4-diol and the second dicarboxylic acid correspond to “k” units. This corresponds to the polymerization degrees “a,” “o,” “e,” and “k” are greater than 0. All other structural units have a degree of polymerization of 0. The limitations that at least one of a, c, m, and o is greater than 0; at least one of e and k is greater than 0; at least one of a, c, and e is greater than 0; and at least one of k, m, and o is greater than 0 are satisfied. Rm1 is a branched chain alkyl group wherein m1=3 (residue derived from isopropylene glycol). Rn1 is an unbranched chain alkyl wherein n1=2 (residue derived from succinic acid). Rn2 is an unbranched chain alkyl wherein 3≤n2≤10 (residue derived from a second polymethylene dicarboxylic acid between glutaric acid and sebacic acid). It is noted that claim 1 does not require a repeating unit with a Rm2 residue (i.e. there is no requirement that at least one of c and m is greater than 0).
As discussed above, one of ordinary skill would have selected the identity and quantity of each ingredient in order to obtain an amorphous copolyester with a Tg below room temperature without crystallization and melting. Nishiwaki provides evidentiary support of the position that the copolyester of modified Fuller would be amorphous and have a Tg below room temperature without crystallization and melting.
Nishiwaki teaches poly(1,2-propylene succinate) referred to by Nishiwaki as PPS (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 an amorphous copolyester of isopropylene glycol and succinic acid exhibiting a Tg 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 and a second dicarboxylic acid. However, Fuller teaches that the greater the number of glycols and dicarboxylic acids used in preparing the polyester, the less will be the tendency to crystallize (Fuller, col. 8, lines 1-5). Therefore, one would not expect the addition of a second dicarboxylic acid in an amount selected to avoid crystallization to cause a copolyester of isopropylene glycol and succinic acid to crystallize. 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 a small amount of cis-2-butene-1,4-diol to cause crystallization. Nishiwak therefore supports the position that a copolyester derived from isopropylene glycol, succinic acid, some amount of a second dicarboxylic acid between glutaric acid and sebacic acid, and cis-2-butene-1,4-diol would be amorphous and exhibit a Tg lower than the room temperature without crystallization and melting.
While not explicitly an elastomer, modified Fuller’s copolyester contains all of the claimed elements and would be expected to be capable of functioning as an elastomer.
Regarding claims 11, 13, and 15, Fuller teaches the butenediol-based elastomer according to claim 1 where m1 is 3, n1 is 2, and 3≤n2≤10. Claims 11, 13, and 15 do not require a repeating unit with a Rm2 residue.
Fuller does not anticipate the n2 values recited in claims 11, 13, and 15.
However, Fuller teaches second dicarboxylic acids corresponding to 3≤n2≤10. 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 selected any n2 in the range of 3≤n2≤10 because Fuller teaches this range. A range of 3≤n2≤10 overlaps with the claimed ranges of 2≤n2≤8 (claim 11), n2 is 8 (claim 13), and n2 is 10 (claim 15). 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 claim 14, Fuller teaches the butenediol-based elastomer according to claim 1 where n1 is 2 and 3≤n2≤10. Claim 14 does not require a Rm2 residue.
Fuller does not anticipate the n2 is 4.
However, Fuller teaches second dicarboxylic acids corresponding to 3≤n2≤10. 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 selected any n2 in the range of 3≤n2≤10, including and n2 of 4, because Fuller teaches this range. A range of 3≤n2≤10 overlaps with n2 is 4. 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.
Fuller teaches substituting a portion of the isopropylene glycol with ethylene glycol without excessive crystallization (col. 7, lines 35-47). It would have been obvious to one of ordinary skill in the art prior to the effective filing date to substitute a portion of the isopropylene glycol (m1=3) with ethylene glycol (m1=2) because Fuller teaches it.
In determining the amount of isopropylene glycol to substitute with ethylene glycol, one would have considered Fuller’s teachings about the impact of ethylene glycol content on crystallinity (col. 7, lines 35-47). Fuller teaches that isopropylene glycol forms a non-crystalline polyester with polymethylene dicarboxylic acids between succinic acid and sebacic acid. When succinic acid (n2=2) is used as the dicarboxylic acid, 50-60% of the isopropylene glycol can be replaced with ethylene glycol without excessive crystallization. When sebacic acid (n2=10) is used as the dicarboxylic acid, up to 30% of the isopropylene glycol can be replaced with ethylene glycol without excessive crystallization. Therefore, one of ordinary skill would have recognized that increasing the amount of ethylene glycol increases the tendency to crystallize. Therefore, one of ordinary skill would have selected an ethylene glycol amount that is low enough to avoid crystallization, as desired by Fuller (col. 6, lines 4-46 and 73-74).
A residue derived from ethylene glycol reads on m1=2. In this case, isopropylene glycol corresponds to another diol that is included in the
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portion of the general formula shown in claim 1 rather than m1.
Response to Arguments
Applicant’s arguments filed June 30, 2026 have been fully considered.
Applicant argues (end of page 9) that modified Fuller (US 2448585) requires each of m, o, and k to be 0 whereas amended claim 1 requires that at least one of k, m, and o is greater than 0. MPEP 2123, subsection II states "[t]he prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed…." In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004). This argument is not persuasive because Fuller teaches the use of multiple dicarboxylic acids, as discussed above in the rejection of claim 1. In particular, Fuller teaches that the greater the number of dicarboxylic acids, the less will be the tendency to crystallize (col. 8, lines 1-5). A copolyester with residues from a second dicarboxylic acid corresponds to at least one of m, o, and k is greater than 0.
Applicant argues (page 10) that Fuller teaches away from an elastomer where n1 and n2 are different from one another and both present in the polyester that has an amorphous structure and exhibits a glass transition temperature (Tg) less than room temperature without crystallization and melting. Applicant points to Fuller’s teaching that substituting a portion of the isopropylene diol with ethylene glycol leads to crystallization behavior at lower contents when the diacid is sebacic acid than when the diacid is succinic acid (col. 7, lines 35-47). Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). See MPEP 2123, subsection II. Applicant further argues that one would not have a reasonable expectation of success in attaining a polyester with an amorphous structure and a Tg less than room temperature without crystallization and melting when substituting the diacid residue. 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. In this case, the two examples pointed to by Applicant are derived from only one type of diacid. These examples do not teach away from or discredit using two diacids. Rather, these examples support Fuller’s broader statements that introduction of sidechain substituents (ethylene glycol vs. isopropylene glycol) and decreasing the polymethylene chain lengths (sebacic acid vs. succinic acid) reduces crystallinity (col. 7, lines 10-16 and 24-28). Fuller goes on to teach that the greater the number of dicarboxylic acids, the less will be the tendency to crystallize (col. 8, lines 1-5). Based on this teaching, one would expect that a combination of two diacids can be used in a copolyester that does not crystallize.
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
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