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 March 28, 2026. Support for amended claim 1 is found in original claim 6 and specification, page 10, lines 6-8. Claim 6 is canceled.
The new grounds of rejection set forth below were necessitated by the amendment to claim 1 narrowing the dicarboxylic acid component and tetracyclobutane-based diol component content. 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Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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 9, filed March 28, 2026, with respect to the rejections under 35 U.S.C. 102(a)(1) over Hoppens (Aliphatic-aromatic copolyesters derived from 2,2,4,4-tetramethyl-1,3-cyclobutanediol, Journal of Polymer Science: Part A: Polymer Chemistry, 2004, Vol. 42, 3473-3478) have been fully considered and are persuasive. Hoppens does not teach a combination of terephthalic acid or dimethyl terephthalate and isophthalic acid or dimethyl isophthalate. The rejections of claims 1-4 and 6-7 over Hoppens have been withdrawn. Upon further consideration, a new ground(s) of rejection is made in view of Kanke (JP-2012007154-A, English translation provided) in view of Furuya (JP-2013049784-A, English translation provided).
Applicant’s arguments with respect to claims 1-4 and 7-10 over Sato (WO 2020/122122 A1) have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument. Sato continues to be relied upon for the combination of cis-tetra-cyclobutane diol and trans-tetra-cyclobutane diol of claim 7, but this teaching has not been specifically challenged.
Claim Rejections - 35 USC § 103
Claims 1-5 and 8-10 are rejected under 35 U.S.C. 103 as being unpatentable over Kanke (JP-2012007154-A, English translation provided) in view of Furuya (JP-2013049784-A, English translation provided).
Regarding claims 1 and 4-5, Kanke teaches a polyester-based resin composition formed from a composition comprising a polyol component and a carboxylic acid component (Kanke, [0019]).
The polyol component comprises a fluorene-based compound (Kanke, [0020]). The fluorene-based compound is preferably bisphenoxyethanol fluorene (BPEF) (Kanke, [0021], the chemical structure in [0018] shows the oxyethanol position), reading on 9,9-bis[4-(2-hydroxy ethoxy)phenyl]fluorene (claim 5) and a bisphenyl fluorene-based diol component represented by Chemical Formula I where R1 is a hydroxyalkyl group having 2 carbon atoms and R2, R3, R4, and R5 are hydrogen (claim 1).
The polyol component further comprises an additional diol that can be 2,2,4,4-tetramethyl-1,3-cyclobutanediol (Kanke, [0022]). The compound 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) reads on claim 4 and a tetracyclobutane-based diol component represented by Chemical Formula II where two of R1 to R8 are hydroxyl groups, two of R1 to R8 are hydrogen atoms, and four of R1 to R8 are alkyl groups having one carbon atom (claim 1).
The fluorene-based compound is present in an amount of 50 mol% of more (Kanke, [0020]). Therefore, it would have been obvious to one of ordinary skill to have included up to about 50 mol% of the additional diol.
Kanke does not anticipate the claimed contents of the bisphenyl fluorene-based diol and tetracyclobutane-based diol components.
However, it would have been obvious to one of ordinary skill to have selected the BPEF content in the range of 50 mol% or more and any TMCD content in the range of up to about 50 mol% because Kanke teaches these ranges. A range of 50 mol% or more of BPEF overlaps with the claimed range of 20-90 mol% bisphenyl fluorene-based diol component. A range of up to about 50 mol% TMCD overlaps with the claimed range of 10-50 mol% of tetracyclobutane-based diol component. 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.
As the carboxylic acid component, Kanke teaches that dicarboxylic acids can be used alone, or in combination of two or more (Kanke, [0024]). The preferred dicarboxylic acids include terephthalic acid and isophthalic acid and esters thereof (Kanke, [0024]). It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any combination of dicarboxylic acids taught by Kanke, including a combination comprising isophthalic acid and terephthalic acid.
Kanke does not teach the relative amounts of each dicarboxylic acid.
However, Furuya teaches suitable monomer ratios in copolyester resins with excellent heat resistance and high refractive index for use in optical applications (Furuya, [0001]). Furuya teaches that the molar ratio of terephthalic and isophthalic acid components is 20:80-70:30 (Furuya, [0016]). Furuya teaches that when the molar ratio of terephthalic acid is 70 mol% or more, birefringence is remarkably exhibited, which is not desirable as an optical resin material and that when the ratio of isophthalic acid is 80 mol% or more, birefringence is reduced but the glass transition temperature (Tg) and heat resistance are lowered which is not preferable (Furuya, [0016]). Based on the disclosure of Furuya, one of ordinary skill would have understood that a molar ratio of terephthalic and isophthalic acid components of 20:80-70:30 is suitable for achieving a suitable balance of birefringence, heat stability, and Tg for optical 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 unspecified terephthalic acid to isophthalic acid ratio of Kanke with the molar ratio of 20:80-70:30 taught by Furuya in order to achieve a suitable balance of birefringence, heat stability, and Tg for optical resins.
Kanke teaches that the Tg is 80-175 °C (Kanke, [0039]).
Kanke does not anticipate the claimed Tg range.
However, it would have been obvious to one of ordinary skill to select any Tg in the range of 80-175 °C because Kanke teaches this range. A range of 80-175 °C overlaps with the claimed range of at least 100 °C. 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 claims 2-3, modified Kanke teaches the polyester-based resin composition of claim 1. Kanke teaches that the dicarboxylic acids can be used alone, or in combination of two or more (Kanke, [0024]). The specific dicarboxylic acids taught by Kanke include terephthalic acid, isophthalic acid and 2,6-napthelenedicarboxylic dimethyl (Kanke, [0024]). Given that Kanke teaches using dicarboxylic acids in a combination of two or more, it would have been obvious to one of ordinary skill to select any three dicarboxylic acids taught by Kanke.
Kanke does not anticipate a combination of terephthalic acid, isophthalic acid and 2,6-napthelenedicarboxylic acid.
However, Furuya teaches that polyamide derived from a combination of terephthalic acid, isophthalic acid and 2,6-napthelenedicarboxylic with a suitable balance of birefringence, heat stability, and Tg. Furuya teaches copolyester resins with excellent heat resistance and high refractive index that are suitable for optical applications (Furuya, [0001]). Furuya teaches a dicarboxylic acid component in which the total amount of terephthalic acid and isophthalic acid is preferably 80 mol% or more and 2,6-napthelenedicarboxylic acid is present in an amount of less than 20 mol% (Furuya, [0015]). Furuya teaches that a 2,6-napthelenedicarboxylic acid content less than 20 mol% is preferable for avoiding significant birefringence (Furuya, [0015]). Furuya teaches a molar ratio of terephthalic and isophthalic acid components of 20:80-70:30 (Furuya, [0016]). Furuya teaches that when the molar ratio of terephthalic acid is 70 mol% or more, birefringence is remarkably exhibited, which is not desirable as an optical resin material and that when the ratio of isophthalic acid is 80 mol% or more, birefringence is reduced but the Tg and heat resistance are lowered which is not preferable (Furuya, [0016]).
Based on the disclosure of Furuya, one of ordinary skill would have understood that a dicarboxylic acid component comprising 80 mol% or more of a combination of terephthalic acid and isophthalic acid and less than 20 mol% 2,6-napthelenedicarboxylic acid is suitable for avoiding excessive birefringence. One would have further understood that a molar ratio of terephthalic and isophthalic acid components of 20:80-70:30 is suitable for achieving a suitable balance of birefringence, heat stability, and Tg for optical 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 dicarboxylic acid of Kanke with a combination of less than 20 mol% 2,6-napthelenedicarboxylic and 80 mol% or more of a combination of terephthalic acid and isophthalic acid with a terephthalic acid to isophthalic acid molar ratio of 20:80-70:30 as taught by Furuya. One would have been motivated to make this substitution in order to achieve a suitable balance of birefringence, heat stability, and Tg for optical resins. One would have had a reasonable expectation of success because Kanke teaches that more than two dicarboxylic acids can be used and Kanke’s example dicarboxylic acids include terephthalic acid, isophthalic acid and 2,6-napthelenedicarboxylic dimethyl (Kanke, [0024]).
Regarding claims 8-10, modified Kanke teaches the polyester-based resin composition of claim 1. Kanke further teaches that two or more polyols compounds may be used in combination as the additional polyol component (Kanke, [0022]). Therefore, it would have been obvious to one of ordinary skill to have used any combination of dihydroxy compounds from those taught for the additional diol of Kanke, including a combination of TMCD and 1,3-propanediol or 1,4-cyclohexanedimethanol (Kanke, [0022]). Including 1,3-propanediol (claim 9) in the additional diol component reads on further including an aliphatic diol component having 3 carbon atoms (claim 8). Including 1,4-cyclohexanedimethanol (claim 10) in the additional diol component reads on further including an alicyclic diol component having 8 carbon atoms (claim 8).
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Kanke (JP-2012007154-A, English translation provided) in view of Furuya (JP-2013049784-A, English translation provided), as applied to claim 1 above and further in view of Sato (WO 2020/122122 A1, Cite No. 1 on 6/13/2023 IDS, references are made to the English translation provided on 1/09/2026).
Modified Kanke teaches the polyester-based resin composition of claim 1.
Kanke is silent as to the cis-trans isomerization of the TMCD.
However, Sato teaches polyester resins used in optical applications (thermoplastic resin for lenses… polyester, Sato, [31]) where the diol component comprises BPEF and TMCD (Sato, [64] and [95]). Sato further teaches that TMCD (dihydroxy represented by Sato formula (1)) is preferably a cis-trans isomer mixture with 30-90 mol% of the cis isomer and that when the cis isomer is in such a range, the moldability of the polymer tends to be good (Sato, [65]). 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 substituted the TMCD of Kanke with a cis-trans isomer mixture of TMCD comprising 30-90 mol% of cis-isomer in order to improve moldability of the polymer.
A cis-trans isomer mixture of TMCD reads on wherein the tetracyclobutane-based diol component represented by Chemical Formula II is a cis-tetra-cyclobutane-based diol and a trans-tetra-cyclobutane diol.
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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