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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 March 3, 2026 has been entered.
Claims 1-12 are pending as amended on March 3, 2026. Support for amended claim 1 is found in original claim 6 and Table 1 (examples 3-4 and 7).
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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 March 3, 2026, with respect to the rejections of claims 1-12 over Kato (US 2019/0055351 A1) in view of Reuter (WO 2019/043060 A1) under 35 U.S.C. 103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. Amended claim 1 requires 3-30 wt.% oligomer, but Kato limits the oligomer content to no more than 2.5 wt.% in order to achieve high thermal stability (Kato, [0036]). However, upon further consideration, a new ground(s) of rejection is made in view of Kato Mariko (JP-2020075980-A) in view of Watanabe (JP-2017014402-A) and Kato Mariko (JP-2020075980-A) in view of Kawaskai (JP-2013231115-A). Kato continues to be relied upon for the thermoplastic resin molecular weight, but this teaching has not been specifically challenged.
Claim Objections
Claim 9 is objected to because of the following informalities:
In claim 9, the phase “Rc and Rd are independently selected from” should be inserted at the beginning of line 3 to specify the subject of the limitation. The suggested wording is consistent with the claims as amended on 9/25/2025.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
Claims 1-2 and 4-12 are rejected under 35 U.S.C. 103 as being unpatentable over Kato Mariko (JP-2020075980-A, English translation provided) in view of Watanabe (JP-2017014402-A, English translation provided).
Regarding claims 1-2, 5-8, and 10-12, Kato Mariko teaches a resin composition that can be used in an optical film or an optical lens (claims 10-12) (Kato Mariko, [0214-0216]). The resin composition comprises a polyester resin and an additive such as a flow control agent (Kato Mariko, [0175]). Kato Mariko’s polyester resin reads on the instant thermoplastic resin is polyester (claim 8).
The polyester is derived from a dicarboxylic acid and a diol (Kato Mariko, [0045]). The diol component can comprise a “third diol” that is preferably 2,2’-bis(2-hydroxyethoxy)-1,1’-binaphthalene (BNE) (Kato Mariko, [0148]). A structural unit derived from BNE reads on a thermoplastic resin containing a structural unit derived from a compound represented by formula (a’). The polyester has a preferred polystyrene-equivalent molecular weight (Mw) of 50,000-60,000 (claim 7) (Kato Mariko, [0173]).
Kato Mariko does not teach a compounding agent having a fluorene structure.
However, Watanabe teaches polycarbonate-based fluorene oligomers that improve the fluidity and reduce the photoelastic constant of resins (Watanabe, [0007]). Like Kato Mariko, Watanabe’s resins are used in optical applications, such as films and lenses (Watanabe, [0108]). Watanabe uses 2-15 parts by weight of the fluorene oligomer with respect to 100 parts of resin (Watanabe, [0106]). The resins include polyester resins (Watanabe, [0104]). The Mw of the fluorene oligomer is 4,000-10,000 (Watanabe, [0085]). The fluorene oligomer is derived from a diol ingredient (Watanabe, [0007-0008]). Preferable diol ingredients include 9,9-bis(hydroxyalkoxyphenyl) fluorenes, such as the one shown below (Watanabe, [0052-0053]):
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.
The compound above is referred to as BPEF (Watanabe, [0110]).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have substituted the flow control agent of Kato Mariko for the polycarbonate-based fluorene oligomer of Watanabe in order to improve the fluidity and reduce the photoelastic constant of the resin. When substituting the flow control agent of Kato Mariko for the oligomer of Watanabe, it would have been obvious to have selected any oligomer taught by Watanabe, including one derived from BPEF with a molecular weight of 4,000-10,000 (claim 5) and to have used it in an amount of 2-15 parts by weight with respect to 100 parts of the polyester resin, as taught by Watanabe, in order to achieve the desired fluidity and photoelastic constant improvements. .
A polycarbonate oligomer (claim 2) derived from BPEF reads on a compounding agent having a fluorene structure containing a compound containing a structure unit represented by general formula (3) where Re and Rf are hydrogen, X is a saturated carbon group with 2 carbon atoms, and e and f are 1. It is noted that while Kato Mariko and Watanabe do not explicitly teach that the oligomer is a compounding agent, the oligomer has the same structure as the instantly claimed compounding agent and would therefore be expected to function as a compounding agent. Case law holds that a recitation of the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967) and In re Otto, 136 USPQ 458, 459 (CCPA 1963).
Modified Kato Mariko teaches 2-15 parts by weight of the compounding agent with respect to 100 parts of the polyester resin. This converts to about 2-13 wt.% compounding agent and a mass ratio of the thermoplastic resin to the compounding agent is thermoplastic resin:compounding agent is about 98:2 to 87:13.
Modified Kato Mariko does not teach a thermoplastic resin:compounding agent ratio of 97:3 to 70:30.
However, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any thermoplastic resin:compounding agent ratio in the range of 98:2 to 87:13 because modified Kato Mariko teaches this range. A range of 98:2 to 87:13 overlaps with the claimed ranges of 97:3 to 70:30 and 96:4 to 70:30 (claim 6). 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 4, modified Kato Mariko teaches the composition of claim 1.
Modified Kato Mariko does not teach the 5% thermal mass reduction onset temperature of the compounding agent.
However, modified Kato Mariko teaches a compounding agent derived BPEF. The instant specification reports the thermal weight reduction onset temperatures of several monomeric and oligomeric compounding agents (Table 1). The closest monomer used in the instant examples is BNEF. Like BPEF, this monomer has a fluorene structure and ethoxy groups. The monomer BNEF has a thermal weight reduction onset temperature of 320 °C (example 2). While the thermal weight reduction onset temperatures of oligomers derived from BPEF are not reported, the oligomerization of BNE to BNE-3PC increased the thermal weight reduction onset temperature from 260 °C to >320 °C (example 4 and example 7). None of the instant examples use compounding agents with thermal weight reduction onset temperatures below 260 °C. Therefore, it is reasonable to expect that the oligomers derived from the BPEF of modified Kato Mariko to necessarily have thermal weight reduction onset temperatures within the claimed range of 260 °C or higher.
Regarding claim 9, modified Kato Mariko teaches the composition of claim 1. Claim 1 contains the limitation that the thermoplastic resin contains a structural unit derived from a compound represented by general formula (a) or formula (a’). Kato Mariko teaches a species without general formula (a) (species where the compound is represented by general formula (a’)). Further limitations of general formula (a), as claimed in claim 4, are made obvious by the rejection over Kato Mariko because neither of claim 1 or claim 4 require a general formula (a).
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Kato Mariko (JP-2020075980-A, English translation provided) in view of Kawaskai (JP-2013231115-A, English translation provided).
Regarding claims 1-2, 5, 7-8, and 10-12, Kato Mariko teaches a resin composition that can be used in an optical film or an optical lens (claims 10-12) (Kato Mariko, [0214-0216]). The resin composition comprises a polyester resin and an additive such as a flow control agent (Kato Mariko, [0175]). Kato Mariko’s polyester resin reads on the instant thermoplastic resin is polyester (claim 8).
The polyester is derived from a dicarboxylic acid and a diol (Kato Mariko, [0045]). The diol component can comprise a “third diol” that is preferably 2,2’-bis(2-hydroxyethoxy)-1,1’-binaphthalene (BNE) (Kato Mariko, [0148]). A structural unit derived from BNE reads on a thermoplastic resin containing a structural unit derived from a compound represented by formula (a’). The polyester has a polystyrene-equivalent molecular weight (Mw) of 50,000-60,000 (claim 7) (Kato Mariko, [0173]).
Kato Mariko does not teach a compounding agent having a fluorene structure.
However, Kawaskai teaches fluorene compounds that have excellent compatibility with thermoplastic resins and improve the fluidity and rigidity of resins (Kawaskai, [0013]). Kawaskai’s thermoplastic resins include polyester resins (Kawaskai, [0012]). Specific examples of Kawaskai’s fluorene compounds include 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene (BPEF) (Kawaskai, [0030] and [0055]). Kawaskai’s thermoplastic resin to fluorene compound ratio is preferably 80:20 to 97:3 (Kawaskai, [0044]). Based on the disclosure of Kawaskai, one of ordinary skill would have understood that the fluorene compounds of Kawaskai, such as BPEF, can be used to modify the fluidity and rigidity of polyester resins.
Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have substituted the flow control agent of Kato Mariko for the fluorene compound of Kawaskai in order to improve the fluidity and rigidity of the resin. When substituting the flow control agent of Kato Mariko for the fluorene compound of Kawaskai, it would have been obvious to have selected any fluorene compound taught by Kawaskai, including BPEF, and to have used it in the amount taught by Kawaskai in order to achieve the desired fluidity and rigidity improvements.
BPEF reads on a compounding agent having a fluorene structure containing a compound containing a structure unit represented by general formula (3) where Re and Rf are hydrogen, X is a saturated carbon group with 2 carbon atoms, and e and f are 1. BPEF has a molecular weight of about 349 g/mol (claim 5) and is a diol monomer with a structural unit represented by general formula (3) (claim 2). A thermoplastic resin:compounding agent ratio in the range of 97:3 to 80:20 falls within the claimed range of 97:3 to 70:30. It is noted that while Kato Mariko and Kawaskai do not explicitly teach that the oligomer is a compounding agent, the oligomer has the same structure as the instantly claimed compounding agent and would therefore be expected to function as a compounding agent. Case law holds that a recitation of the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967) and In re Otto, 136 USPQ 458, 459 (CCPA 1963).
Regarding claim 3, modified Kato Mariko teaches the composition of claim 2. Claim 2 contains the limitation that the compounding agent is a diol monomer or a polycarbonate oligomer. Kato Mariko teaches a species without a polycarbonate oligomer (species where the compounding agent is a diol monomer). Further limitations of the polycarbonate oligomer, as claimed in claim 3, are made obvious by the rejection over Kato Mariko because neither of claim 2 or claim 3 require a polycarbonate oligomer.
Regarding claim 4, modified Kato Mariko teaches the composition of claim 1.
Modified Kato Mariko does not teach the 5% thermal mass reduction onset temperature of the compounding agent.
However, modified Kato Mariko teaches BPEF as the compounding agent and this compound would necessarily exhibit the claimed 5% thermal mass reduction onset temperature. The instant specification reports the thermal weight reduction onset temperatures of several monomeric and oligomeric compounding agents (Table 1). The closest monomer used in the instant examples is BNEF. Like BPEF, this monomer has a fluorene structure and ethoxy groups. BNEF has a thermal weight reduction onset temperature of 320 °C (example 2). None of the instant examples use compounding agents with thermal weight reduction onset temperatures below 260 °C. Therefore, it is reasonable to expect the BPEF of modified Kato Mariko to necessarily have a thermal weight reduction onset temperature within the claimed range of 260 °C or higher.
Regarding claim 6, modified Kato Mariko teaches the composition of claim 1 where the thermoplastic resin to compounding agent ratio is 97:3 to 80:20.
Modified Kato Mariko does not teach a thermoplastic resin to compounding agent ratio of 96:4 to 70:30.
However, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any thermoplastic resin:compounding agent ratio in the range of 97:3 to 80:20 because modified Kato Mariko teaches this range. A range of 97:3 to 80:20 overlaps with the claimed range of 96:4 to 70:30. 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 9, modified Kato Mariko teaches the composition of claim 1. Claim 1 contains the limitation that the thermoplastic resin contains a structural unit derived from a compound represented by general formula (a) or formula (a’). Kato Mariko teaches a species without general formula (a) (species where the compound is represented by general formula (a’)). Further limitations of general formula (a), as claimed in claim 4, are made obvious by the rejection over Kato Mariko because neither of claim 1 or claim 4 require a general formula (a).
Double Patenting
Claims 1, 4, and 6-9 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 4 of U.S. Patent No. 9,982,129 (reference patent) in view of Kato (US 2019/0055351 A1, citation “A” on 3/20/2023 IDS).
Regarding claims 1 and 6-8, reference claim 4 depends from reference claim 1 and teaches a resin composition comprising a polycarbonate resin (A) having the structure
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where X is an alkylene group with 1-4 carbon atoms and a polycarbonate resin (B) having the structure
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(ref claim 1). R1 and R2 are each a hydrogen atom, an alkyl group with a carbon number of 1-20, an alkoxy group with a carbon number of 1-20, a cycloalkyl group with a carbon number of 5-20, a cycloalkyloxyl group with a carbon number of 5-20, an aryl group with a carbon number of 6-20, an aryl group with a carbon number of 6-20, or an aryloxy group with a carbon number of 6-20 (ref claim 1). Y represents an alkylene group with a carbon number of 1-4 (ref claim 1).
The polycarbonate resin (A) reads on the instant thermoplastic resin contains a structural unit derived from a compound represented by general formula (a’) and is a polycarbonate resin (claim 8).
The polycarbonate resin (B) reads on a compounding agent having a fluorene structure containing a compound containing a structure unit represented by general formula (3) where Re and Rf are hydrogen, X is a saturated carbon group with 1-4 carbon atoms, and e and f are 1. It is noted that while reference claim 4 does not explicitly teach that polycarbonate resin (B) is a compounding agent, polycarbonate resin (B) has the same structure as the instantly claimed compounding agent and would therefore be expected to function as a compounding agent.
Reference claim 4 teaches that the mass ratio of the polycarbonate resin (A) to the polycarbonate resin (B) is 25:75-90:10 (reference claim 4). This corresponds to a thermoplastic resin:compounding agent ratio is 25:75-90:10.
Reference claim 4 does not teach a thermoplastic resin:compounding agent ratio of 97:3 to 70:30.
However, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any thermoplastic resin:compounding agent ratio in the range of 25:75-90:10 because reference claim 4 teaches this range. A range of 25:75-90:10 overlaps with the claimed ranges of 97:3 to 70:30 and 96:4 to 70:30 (claim 6). 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.
Reference claim 4 is silent as to the thermoplastic resin molecular weight.
However, Kato teaches polycarbonate resins for optical applications (Kato, [0006]). Kato teaches that a molecular weight range of 20,000-60,000 is favorable for the thermoplastic resin (Kato, [0049-0050]). Below this range, the molded article becomes brittle while above this range, the melt viscosity is increased and thus removal of the resin from a mold becomes difficult (Kato, [0050]). Given the disclosure of Kato, it would have been obvious to one of ordinary skill to have selected a molecular weight of 20,000-60,000 g/mol in order to balance brittleness and mold removal (claim 1 and 7).
Regarding claim 4, modified reference claim 4 teaches the composition of claim 1, but does not teach the 5% thermal mass reduction onset temperature of the compounding agent.
However, modified reference claim 4 teaches a compounding agent derived BPEF. The instant specification reports the thermal weight reduction onset temperatures of several monomeric and oligomeric compounding agents (Table 1). The closest monomer used in the instant examples is BNEF. Like BPEF, this monomer has a fluorene structure and ethoxy groups. The monomer BNEF has a thermal weight reduction onset temperature of 320 °C (example 2). While the thermal weight reduction onset temperatures of oligomers derived from BPEF are not reported, the oligomerization of BNE to BNE-3PC increased the thermal weight reduction onset temperature from 260 °C to >320 °C (examples 4 and 7). None of the instant examples use compounding agents with thermal weight reduction onset temperatures below 260 °C. It would therefore be reasonable to expect that polycarbonates derived from BPEF would also have a thermal weight reduction onset temperature that is at least as high as the BPEF monomer. Therefore, it is reasonable to expect that oligomers derived from the BPEF of modified reference claim 4 necessarily have thermal weight reduction onset temperatures within the claimed range of 260 °C or higher.
Regarding claim 9, reference claim 4 teaches the composition of claim 1. Claim 1 contains the limitation that the thermoplastic resin contains a structural unit derived from a compound represented by general formula (a) or formula (a’). Reference claim 4 teaches a species without general formula (a) (species where the compound is represented by general formula (a’)). Further limitations of general formula (a), as claimed in claim 9, are made obvious by the rejection over reference claim 4 because neither of claim 1 or claim 9 require a general formula (a).
Claims 1-2 and 5-9 provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 30 of copending Application No. 19/132,577 in view of Kato (US 2019/0055351 A1, citation “A” on 3/20/2023 IDS).
Reference claim 30 depends from claim 23 and claim 23 depends from claim 19. Claim 19 claims a thermoplastic resin comprising a structural unit comprising the naphthalene structure shown below (ref claim 1):
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where R1 and R2 can be independently halogens, C1-C4 alkyls, phenyl, or naphthyl and p and q are 0, 1, or 2 (variable definitions are in ref claim 2). Reference claim 23 specifies that the resin is a copolycarbonate, copolyestercarbonate or copolyester resin (ref claim 23, lines 2-3). Reference claim 30 specifies that the resin comprises 9% by weight or less of low molecular weight compounds having molecular weight of less than 1000 based on the total weight of the thermoplastic resin.
The resin of reference claim 30 reads on a resin composition comprising a thermoplastic resin (portion of resin with molecular weight above 1,000) and a compounding agent (portion of resin with molecular weight below 1,000) having a naphthalene structure. The compounding agent having a naphthalene structure contains a compound containing a structural unit represented General formulae (2) where c and d are 0 and Rc and Rd are independently halogen atoms, an alkyl group with 1-4 carbon atoms (C1-C4 alkyl) or an aryl group with 6 or 10 carbon atoms (phenyl or naphthyl). The thermoplastic resin contains a structural unit derived from a compound represented by general formula (a) where c and d are 0 and Rc and Rd are independently halogen atoms, an alkyl group with 1-4 carbon atoms or an aryl group with 6 or 10 carbon atoms (claim 9). When the resin is a copolycarbonate resin (claim 8), the low molecular weight component will be a polycarbonate oligomer (claim 2). The low molecular weight component has a molecular weight of less than 1,000 (claim 5).
It is noted that while reference claim 30 does not explicitly teach that the low molecular weight component is a compounding agent, low molecular weight component has the same structure as the instantly claimed compounding agent and would therefore be expected to function as a compounding agent.
Reference claim 30 does not anticipate a thermoplastic resin:compounding agent ratio of 97:3 to 70:30.
However, reference claim 30 teaches a thermoplastic resin:compounding agent ratio of about 100:0 to 91:9 (9% by weight or less of low molecular weight compounds).
It would have been obvious to one of ordinary skill in the art to have selected any thermoplastic resin:compounding agent ratio in the range of about 100:0 to 91:9 because reference claim 30 teaches this range. A range of 100:0 to 91:9 overlaps with the claimed ranges of 97:3 to 70:30 and 96:4 to 70:30 (claim 6). 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.
Reference claim 30 is silent as to the thermoplastic resin molecular weight.
However, Kato teaches polycarbonate resins for optical applications (Kato, [0006]). Kato teaches that a molecular weight range of 20,000-60,000 is favorable for the thermoplastic resin (Kato, [0049-0050]). Below this range, the molded article becomes brittle while above this range, the melt viscosity is increased and thus removal of the resin from a mold becomes difficult (Kato, [0050]). Given the disclosure of Kato, it would have been obvious to one of ordinary skill to have selected a molecular weight of 20,000-60,000 g/mol in order to balance brittleness and mold removal (claim 1 and 7).
This is a provisional nonstatutory double patenting rejection.
Conclusion
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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