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 1-5 and 7-10 are pending as amended on May 8, 2026. Support for amended claims 1 and 7 is found in original claim 6 and [0015] of the specification. Claim 6 has been cancelled.
The new grounds of rejection set forth below were necessitated by the amendments to claims 1 and 7 incorporating claim 6 and limiting the glass transition temperature of the aromatic polyester resin. 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Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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, see page 8, filed May 8, 2026, with respect to the rejections of claims 1-5 and 7-10 and under 35 U.S.C. 103 have been fully considered and are persuasive. Claims 1 and 7 have been amended to limit the glass transition temperature of the aromatic polyester resin (A). Schure (US 4,093,675) does not teach or suggest a glass transition temperature in the range of -10 to 100 °C. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Sonoda (WO-2018179707-A1).
Claim Rejections - 35 USC § 103
Claims 1-5 and 7-8 are rejected under 35 U.S.C. 103 as being unpatentable over Sonoda (WO-2018179707-A1, English translation provided).
Regarding claims 1-5 and 7, Sonoda teaches crosslinking an epoxy resin and a polyester resin having a carboxy group ([0035]). It would have been obvious to select any carboxylic acid group-containing polyester resins taught by Sonoda, including Example A-11 ([0085]-[0086] and Table 2, English translations of Tables 1-2 are included on page 26 of the translation). Example A-11 is substantially identical to instant polyester resin A-1 (instant Tables 1-2). Both resins are derived from the same monomers in the same ratios and have number average molecular weights (Mn) of 16,000, acid values of 17 mg KOH/g, and glass transition temperatures (Tg’s) of 15 °C. The methods of producing the polyesters are the same (see Sonoda [0077-0079] for the synthesis of A1-4 and A2-1 and [0085-0086] for the synthesis of A-11; see instant [0070-0071] for the synthesis of A1-1 and A1-2 and [0076] for the synthesis of A-1). Sonoda’s A-11 and the A1-4 and A2-1 polyesters from which A-11 is derived are indicated in the translations of Sonoda’s tables below. A-11 corresponds to instant A-1, A1-4 corresponds to instant A1-1, and A2-1 corresponds to instant A1-2.
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Example A-11 reads on the claimed aromatic polyester resin having a carboxy group on a side chain (A). Example A-11 is a polyester derived from aromatic monomers (terephthalic acid and isophthalic acid). While the carboxy groups are not explicitly on a side chain, there is reasonable basis to conclude that Example A-11 has carboxy groups on a side chain because Example A-11 is substantially similar to instant A-1 and prepared in a substantially similar method. Example A-11 has a Tg of 15 °C (claim 1), an acid value of 17 mg KOH/g (claim 2), and a Mn of 16,000 (claim 3).
It would have been obvious to use any epoxy resin taught by Sonoda, including bisphenol-A diglycidyl ether ([0037]). Bisphenol-A diglycidyl ether has a molecular weight of about 340 g/mol (claim 5).
Sonoda does not anticipate the molar ratio of the carboxy group of the aromatic polyester resin to the epoxy group of the epoxy compound recited in claim 4.
However, the molar ratio resulting from the epoxy content taught by Sonoda overlaps with the claimed molar ratio and Sonoda provides motivation to optimize the epoxy content. Sonoda teaches using 2-50 parts by mass of epoxy resin per 100 parts by mass of the carboxylic acid group-containing polyester resin ([0038]). Sonoda teaches that too little epoxy leads to insufficient curing and decreased adhesiveness and moist heat resistance, but too much epoxy leads to uncrosslinked epoxy and decreased soldering resistance ([0038]). Using a 1 mole of polyester resin basis (16,000 g), Sonoda’s epoxy content corresponds to about 320-8000 g of epoxy. Bisphenol-A diglycidyl ether has a molecular weight of about 340 g/mol and two epoxy groups per molecule. Sonoda therefore teaches about 2-47 moles of epoxy groups (2*8000/340=47.06). Because example A-11 is the same as instant A-1, it is reasonable to use the number of carboxy groups per molecular chain reported in instant Table 2 for comparing the catalyst content taught by Sonoda to the molar ratio recited in claim 4. Each polyester chain has about 4.8 carboxy groups, so Sonoda’s epoxy content corresponds to a molar ratio of the carboxy group of the aromatic polyester resin to epoxy groups of the epoxy compound of about 100:42 to 100:980 (47/4.8=9.79).
It would have been obvious to one of ordinary skill to have selected any molar ratio in the range of 100:42 to 100:980 because Sonoda teaches this range. A range of 100:42 to 100:980 overlaps with the claimed range of 100:50 to 100:150 (claim 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. Furthermore, based on the teachings of Sonoda, one of ordinary skill in the art would have understood that too little epoxy leads to insufficient curing and decreased adhesiveness and moist heat resistance, but that too much epoxy leads to uncrosslinked epoxy and decreased soldering resistance ([0038]). Therefore, it would have been obvious to one of ordinary skill to have optimized the molar ratio of the carboxy group of the aromatic polyester resin to epoxy groups of the epoxy compound of Sonoda into the claimed range of 100:50 to 100:150 (claim 4) in order to balance the degree of curing, adhesiveness, moist heat resistance, and soldering resistance. The discovery of an optimum value of a known result effective variable, without producing any new or unexpected results, is within the ambit of a person of ordinary skill in the art. See In re Boesch, 205 USPQ 215 (CCPA 1980) (see MPEP § 2144.05, II.).
Sonoda further teaches that a curing catalyst can be used to enhance the reaction between the polyester resin and the epoxy resin and provide strong adhesion performance ([0039]). It would have been obvious to use any curing catalyst taught by Sonoda, including 1,8-diazabicyclo(5,4,0)-undecene-7 ([0039]). This catalyst reads on a transesterification catalyst (see [0051] of the instant specification).
Sonoda does not anticipate the claimed molar ratio of the carboxy group of the aromatic polyester resin to the transesterification catalyst.
However, the molar ratio resulting from the catalyst content taught by Sonoda overlaps with the claimed molar ratio. Sonoda teaches using the catalyst in an amount of 0.01 to 10 parts by weight per 100 parts by weight of the carboxylic acid group-containing polyester resin ([0039]). Using a 1 mole of polyester resin basis (16,000 g), a catalyst content of Sonoda corresponds to about 1.6-160 g of catalyst. The catalyst (1,8-diazabicyclo(5,4,0)-undecene-7) has a molecular weight of about 152 g/mol, so Sonoda teaches about 0.01-1 moles of catalyst (160/152=1.05). Each polyester chain has about 4.8 carboxy groups. Sonoda’s catalyst content therefore corresponds to a molar ratio of the carboxy group of the aromatic polyester resin to the transesterification catalyst of about 100:0.2 to 100:20 (1/4.8=0.208). It would have been obvious to one of ordinary skill to have selected any molar ratio in the range of 100:0.2 to 100:20 because Sonoda teaches this range. A range of 100:0.2 to 100:20 overlaps with the claimed range of 100:10 to 100:40. 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.
Sonoda further teaches preparing an adhesive sheet (reading on crosslinked aromatic polyester resin composition) by curing the adhesive composition ([0049]). Sonoda teaches curing by heat treatment ([0089], [0093]), reading on heating. The adhesive composition comprises the polyester resin, epoxy compound, and transesterification catalyst ([0039-0040]). While Sonoda does not explicitly teach mixing the components, one of ordinary skill would recognize that for the polyester resin and the epoxy compound to form a network, the components of the reaction would necessarily require some degree of mixing for the epoxy and polyester compounds to come into contact. Sonoda therefore teaches a method for preparing a crosslinked aromatic polyester resin composition comprising mixing and heating the aromatic polyester resin, epoxy compound, and transesterification catalyst (claim 7).
Sonoda does not explicitly teach a A3200-3600/A1730 ratio.
However, Sonoda teaches a substantially similar crosslinked polyester prepared in a substantially similar method as the instant application and provides motivation to optimize the epoxy content. Sonoda teaches crosslinking an aromatic polyester resin having a carboxy group on a side chain (resin of example A-11) with an epoxy resin in the presence of a transesterification catalyst. Like the instant application, Sonoda obtains the crosslinked resin by mixing and heating the polyester, epoxy compound, and transesterification catalyst (instant specification, [0008]). As discussed above, Sonoda teaches the same polyester as instant example A-1. Instant Table 4 shows the composition of several crosslinked polyesters prepared from the A-1 resin. Instant Examples 1,2, 5, and 6 all have A3200-3600/A1730 ratios within the claimed range. These examples are derived from a composition comprising 10-20 parts transesterification catalyst and 25-50 parts epoxy compound per 100 parts of the carboxy group of the A-1 polyester resin. Even Comparative examples 3-5 where the transesterification catalyst is not included have A3200-3600/A1730 ratios within the claimed range. None of the examples derived from resin A-1 in Table 4 have A3200-3600/A1730 ratios outside of the claimed range. Sonoda teaches an epoxy content that encompasses the epoxy contents used in the examples and recited in claim 4 and also provides motivation to optimize the epoxy content. Therefore, it would have been obvious to one of ordinary skill to have selected an epoxy content that would necessarily produce a A3200-3600/A1730 ratio within the claimed range of 0.005-0.038 in order to balance the degree of curing, adhesiveness, moist heat resistance, and soldering resistance.
Regarding claim 8, Sonoda teaches the crosslinked aromatic polyester resin composition of claim 1. Sonoda further teaches that the resin composition is useful as an adhesive (Schure, col. 5, lines 4-7), reading on a self-adhesive agent.
Claims 8-10 are rejected under 35 U.S.C. 103 as being unpatentable over Sonoda (WO-2018179707-A1, English translation provided) as applied to claim 1 above, and further in view of Hayashi (WO-2020045439-A1, Cite No. BA on 4/13/2023, English translation provided with 2/10/2026 Office action).
Sonoda teaches the crosslinked aromatic polyester resin composition according to claim 1. Sonoda teaches that the composition is useful as an adhesive ([0001]), but is silent as to the use of the composition in a self-repairing material or a molding material.
However, prior to the effective filing date, crosslinked polyester resin compositions were known as components in self-adhesive agents, self-repairing materials, and in molding materials, as evidenced by Hayashi. Hayashi teaches a cross-linked polyester resin film exhibiting self-adhesiveness, re-moldability, and wound repairability (Hayashi, [1]). A self-adhesive material reads on a self-adhesive agent, a re-moldable material reads on a molding material and a wound-repairing material reads on a self-healing material. The cross-linked polyester resin film of Hayashi is obtained by mixing a polyester resin raw material containing an ester bond and a carboxylic acid group at multiple points, a diepoxy crosslinking agent, and the transesterification catalyst, and heating and crosslinking (Hayashi, [11]). Given the disclosure of Hayashi, one of ordinary skill in the art would have understood that a cross-linked polyester resin derived from a polyester resin containing carboxylic acid groups with a diepoxy crosslinking and containing a transesterification catalyst would be useful in materials with self-adhesive, re-moldability, and wound repairability properties.
Therefore, it would have been obvious to one of ordinary skill prior to the effective filing date of the claimed invention to have used the crosslinked aromatic polyester resin composition of Sonoda in a self-adhesive agent (claim 8), self-repairing material (claim 9), or molding material (claim 10).
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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