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 .
Specification
The abstract of the disclosure is objected to because the abstract exceeds 150 words in length. The abstract should be in narrative form and generally limited to a single paragraph within the range of 50 to 150 words in length. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b) for guidelines for the preparation of patent abstracts.
Claim Rejections - 35 USC § 103
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.
Claims 1-5 and 7-8 are rejected under 35 U.S.C. 103 as being unpatentable over Schure (US 4,093,675; AA on 4/13/2023 IDS).
Regarding claims 1-5, Schure teaches a carboxylated poly(ester/ether) block copolymer that is useful as an adhesive upon being crosslinked with epoxy resins (Schure, col. 5, lines 4-7).
The carboxylated poly(ester/ether) block copolymer of Schure has the formula below (Schure, col. 2, lines 23-35):
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where -O--O- is the residue of a linear hydroxy-terminated poly(ester/ether) block copolymer, R is an alkyl, cycloalkyl, or aryl, and n is 1-2. The COOH groups in the formula above read on carboxy groups on a side chain. The linear hydroxy-terminated poly(ester/ether) block copolymer (-O--O- in the formula above) has “hard” (on left below) and “soft” (on right below) segments, such as those shown below (Schure, end of col. 3 to beginning of col. 4):
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The hard and soft segments pictured above comprise aromatic groups. The carboxylated poly(ester/ether) block copolymer of Schure therefore reads on an aromatic polyester resin (A) having a carboxy group on a side chain.
Schure further teaches that the polyester is synthesized in the presence of an ester interchange catalyst (Schure, col. 6, lines 26-27). An ester interchange catalyst reads on the instantly claimed transesterification catalyst (D). Because Schure does not teach removing the catalyst, one of ordinary skill would expect the catalyst to be present during the subsequent crosslinking step and in the resulting crosslinked polyester resin.
Schure teaches an acid value of about 5 to about 60 (Schure, col. 4, lines 40-44). The acid value of Schure reads on wherein the aromatic polyester resin (A) has an acid value of 5 mg KOH/g to 60 mg KOH/g (claim 2).
Schure further teaches a molecular weight of 6,000 to 50,000 (Schure, col. 2, lines 49-55). Schure does not explicitly state that the molecular weight is a number average molecular weight (Mn). However, Schure determines molecular weight by end group analysis, suggesting that the molecular weight is a Mn. In addition, even if the molecular weight range taught by Schure were a weight average molecular weight (Mw), there would most likely be overlap with the claimed range because polydispersity index values up to about 6 correspond to Mn above 8,000 when Mw is 50,000. The range of 6,000-50,000 taught by Schure overlaps with the claimed range of wherein the aromatic polyester resin (A) has a number average molecular weight of not lower than 8000 (claim 3). 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.
The polyester of Schure is reacted with approximately stoichiometric amounts of an epoxy resin to accomplish crosslinking (Schure, col. 8, lines 63-66). This corresponds to wherein a molar ratio of the carboxy group of the aromatic polyester resin (A) to an epoxy group of the epoxy compound (B) is about 100:100 (claim 4).
Schure teaches that suitable epoxy compounds include those based on bisphenol A and epichlorohydrin that have average molecular weights from about 175-4000 (Schure, col. 5, lines 13-16). A range of 175-4000 overlaps with the claimed range of wherein the epoxy compound (B) has a number average molecular weight of not lower than 100 and not higher than 500 (claim 5). 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.
Instant claim 1 specifies that the A3200-3600 infrared spectroscopy peak is derived from a hydroxyl group, the A1730 peak is derived from ester bonds, and the ratio between them (A3200-3600/A1730) is not lower than 0.005 and not higher than 0.038. Schure is silent as to the A3200-3600/A1730 ratio of the crosslinked composition as measured by infrared spectroscopy.
However, Schure teaches a crosslinked aromatic polyester resin that would be expected to produce a A3200-3600/A1730 ratio within the claimed range. Schure teaches a polyester with an acid number within the range of claim 2 and a molecular weight range that overlaps with claim 3. Furthermore, the carboxy group: epoxy group ratio used in the crosslinking is approximately 100:100, satisfying claim 4. In addition, the polyester of Schure, such as the structures shown above, is derived from similar monomers as those in the instant specification. Specifically, the instant specification teaches aliphatic glycols such as 1,4-butanediol ([0020]), ether-bond containing glycols such as polytetramethylene glycol ([0024]), and terephthalic acid as a carboxylic acid component ([0018]). Because the polyester of Schure has the same concentration of COOH groups (acid number) as the instant invention and there is enough epoxy for those COOH groups to react to produce the OH groups corresponding to an A3200-3600 peak, it is reasonable to expect that Schure would have an A3200-3600 peak of a similar magnitude to the instant invention. Similarly, because the polyester is derived from the same monomers and has the same molecular weight as the instant invention, it is reasonable to expect that the relative number of OH bonds to ester bonds would lead to an A3200-3600/A1730 ratio within the range of 0.005 to 0.038.
Therefore, Schure teaches a crosslinked aromatic polyester resin composition, comprising a crosslinked aromatic polyester resin (C) (carboxylated poly(ester/ether) block copolymer crosslinked with epoxy resins) and a transesterification catalyst (D) (ester interchange catalyst), wherein the crosslinked aromatic polyester resin (C) is a reaction product of an aromatic polyester resin (A) having a carboxy group on a side chain and an epoxy compound (B) and an A3200-3600/A1730 ratio within the range of 0.005 to 0.038 (claim 1).
Regarding claim 7, Schure teaches a crosslinked aromatic polyester resin composition derived from an aromatic polyester resin (A) having a carboxy group on a side chain and having an acid value of not lower than 5 mg KOH/g and not higher than 60 mg KOH/g and an epoxy compound (B), as discussed above for claims 1 and 2. Furthermore, Schure further teaches that the polyester is synthesized in the presence of an ester interchange catalyst (Schure, col. 6, lines 26-27). An ester interchange catalyst reads on the instantly claimed transesterification catalyst (D). Because Schure does not teach removing the catalyst, one of ordinary skill would expect the catalyst to be present during the subsequent crosslinking step and in the resulting crosslinked polyester resin.
Schure further teaches that the crosslinking reaction is carried out in a temperature range of 150-235 °C (Schure, end of col. 8 to beginning of col. 9), reading on heating. While Schure does not explicitly teach mixing the polyester resin, epoxy compound, and transesterification catalysts, one of ordinary skill would recognize that for the polyester resin and the epoxy compound to form a crosslinked network, the components of the reaction would necessarily require some degree of mixing for the epoxy and polyester compounds to come into contact. Schure therefore teaches a method for preparing a crosslinked aromatic polyester resin composition, the method comprising mixing and heating an aromatic polyester resin (A) having a carboxy group on a side chain and having an acid value of not lower than 5 mg KOH/g and not higher than 60 mg KOH/g, an epoxy compound (B), and a transesterification catalyst (D) to perform crosslinking.
Regarding claim 8, Schure teaches the crosslinked aromatic polyester resin composition according to claim 1. Schure 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 Schure (US 4,093,675; AA on 4/13/2023 IDS) 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, referred to as Hayashi 2020).
Schure teaches the crosslinked aromatic polyester resin composition according to claim 1. Schure teaches that the composition is useful as an adhesive (Schure, col. 5, lines 4-7), 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 2020. Hayashi 2020 teaches a cross-linked polyester resin film exhibiting self-adhesiveness, re-moldability, and wound repairability (Hayashi 2020, [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 2020 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 2020, [11]). Given the disclosure of Hayashi 2020, one of ordinary skill in the art would have understood that a cross-linked polyester resin containing a transesterification catalyst and a cross-linked polyester derived from a polyester resin containing carboxylic acid groups with a diepoxy crosslinking 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 according to claim 1 in a self-adhesive agent (claim 8), self-repairing material (claim 9), or molding material (claim 10).
Claims 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Schure (US 4,093,675; AA on 4/13/2023 IDS) as applied to claim 1 above, and further in view of Hayashi (Synthesis of amorphous low Tg polyesters with multiple COOH side groups and their utilization for elastomeric vitrimers based on post-polymerization cross-linking, Polymer Chemistry, 2019, 10, 2047-2056).
Schure teaches the crosslinked aromatic polyester resin composition according to claims 1-5 made by the method of claim 7, as described above. Schure is silent as to the amount of transesterification catalyst in the composition.
However, Hayashi teaches a polyester (Hayashi, title) with COOH functional groups that is cross-linked using an epoxy, as illustrated in Hayashi figure 1 (Hayashi, page 2048, figure 1):
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In addition to the polyester and epoxy components, the composition comprises a transesterification catalyst (Zn(OAc)2). During the crosslinking, the catalyst is used in an amount of 20 mol% based on the COOH groups (Hayashi, page 2049, right column, last paragraph). This corresponds to a carboxy group:transesterification catalyst of 100:20. Hayashi also teaches that the crosslinked network heals when heated and have self-adhesion properties (Hayashi, page 2053, figure 5 and page 2054, col. 1, lines 2-6). Based on the disclosure of Hayashi, one of ordinary skill would have recognized that including a transesterification catalyst in the amount taught by Hayashi is suitable for enabling the composition to crosslink and further heal when heated.
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 included 20 mol% based on the COOH groups of a transesterification catalyst as taught by Hayashi when crosslinking the polyester of Schure (claim 6). One would have been motivated to use this amount of catalyst in order to utilize a catalyst amount that has been demonstrated to be suitable for enabling polyester and epoxy crosslinking and subsequent healing when heated. Using the catalyst content taught by Hayashi in the composition of Hayashi represents the use of a suitable range of catalyst content in a similar adhesive application. "The combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results." KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 416-21 (2007). See MPEP 2141.
Including a transesterification catalyst in an amount of 20 mol% based on the COOH groups would be expected to produce a crosslinked aromatic polyester resin with a A3200-3600/A1730 ratio within the range of claim 1. As discussed above, Schure teaches a polyester with an acid number within the range of claim 2 and a molecular weight range that overlaps with claim 3. Furthermore, the carboxy group: epoxy group ratio used in the crosslinking is approximately 100:100, satisfying claim 4. The molecular weight range of the epoxy of Schure overlaps with that of claim 5. In addition, the polyester of Schure, such as the structures shown above, is derived from similar monomers as those in the instant specification. Specifically, the instant specification teaches aliphatic glycols such as 1,4-butanediol ([0020]), ether-bond containing glycols such as polytetramethylene glycol ([0024]), and terephthalic acid as a carboxylic acid component ([0018]). Because the polyester of Schure has the same concentration of COOH groups (acid number) as the instant invention, there is enough epoxy for those COOH groups to react to produce the OH groups corresponding to an A3200-3600 peak, and the catalyst to COOH group ratio is within the range of claim 6, it is reasonable to expect that Schure would have an A3200-3600 peak of a similar magnitude to the instant invention. Similarly, because the polyester is derived from the same monomers and has the same molecular weight as the instant invention, it is reasonable to expect that the relative number of OH bonds to ester bonds would lead to an A3200-3600/A1730 ratio within the range of 0.005 to 0.038 (claim 1).
The crosslinked aromatic polyester resin composition of modified Schure satisfies claims 1-6 and is made by the method of claim 7.
The composition has an amount of transesterification catalyst that has been shown by Hayashi to support self-healing and self-adhesion (Hayashi, page 2053, figure 5 and page 2054, col. 1, lines 2-6). Given the disclosure of Hayashi, one of ordinary skill in the art would have understood that a cross-linked polyester resin containing a transesterification catalyst and a cross-linked polyester derived from a polyester resin containing carboxylic acid groups with a diepoxy crosslinking would be useful as a material with self-adhesiveness and wound repairability. 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 according to claim 1 in a self-adhesive agent (claim 8) or self-repairing material (claim 9).
Hayashi further teaches preparing samples using a mold (Hayashi, page 2054, column 1, lines 16-18). Given the disclosure of Hayashi, one of ordinary skill in the art would have understood that a cross-linked polyester resin containing a transesterification catalyst and a cross-linked polyester derived from a polyester resin containing carboxylic acid groups with a diepoxy crosslinking is moldable. 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 according to claim 1 in molding material (claim 10).
Conclusion
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