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 .
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 5-6, 8 and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Cohen et al. WO2017/085158 (provided on IDS).
Cohen teaches polyester polyol based on a carboxylic acid component (A) which comprises at least one carboxylic acid having 2 carboxyl groups and an alcohol component (B) which comprises at least [5-(hydroxymethyl)tetrahydrofuran-2 yl]methanol and processes for preparing such polyester polyols (Abstract).
Regarding claims 1, 5 and 8, Cohen discloses inventive example 5 (page 17, lines 5-11, and reference claim 11), where the dihydroxy monomer is: [5-(hydroxymethyl)tetrahydrofuran-2-yl]methanol (tetrahydrofuran dimethanol), with structure as presented below, which meets the requirement of Chemical Formula 3 (instant claim 8), where A11 and A12 are C1 aliphatic groups and n12 =0:
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Cohen utilizes adipic acid as the aliphatic dicarboxylic acid which is represented by the formula as shown below and corresponds to applicant’s Chemical Formula 4 (instant claim 8), where A13 is C4 linear aliphatic groups and both X31 and X32 are hydroxyl groups.
The polycondensation reaction results in the formation of the final polyester with the repeat unit structure as depicted below, which meets the requirement of Chemical Formula 1,with n11 >1(instant claims 1 and 8).
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Since Cohen’s inventive example 5 polyester is derived from only two monomers adipic acid and [5-(hydroxymethyl)tetrahydrofuran-2-yl]methanol, 100 mol% of the repeat units would be represented by formula corresponding to Chemical Formula 1 (instant claim 5).
The invention as claimed is fully anticipated by Cohen as disclosing each limitation of the rejected claims as per discussion above.
Regarding claims 6 and 11, as discussed when addressing claims 1 and 8, Cohen’s inventive example 5 is derived from adipic acid and tetrahydrofuran dimethanol (THFDM). Cohen’s teaches inventive example 6 (page 17, lines 19-27), where along with adipic acid and THFDM, additional aromatic dicarboxylic acid: furandicarboxylic acid is introduced for the formation of the polyester (instant claims 6 and 11). Cohen’s inventive example 6 utilizes moles of adipic acid =(202.9g ÷146.142 g/mol) = 1.39 mol and moles of furandicarboxylic acid = (72.2g÷156.09 g/mol) =0.463 mol. The mol% of repeat unit corresponding to chemical formula 1 derived from adipic acid and THFDM is determined by the mol % of the adipic acid in the total acid monomers = 1.39 ÷ (1.39+0.463) = 75 mol%, and meets the claimed requirement (as required by claim 5).
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 7, 12 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Cohen et al. WO2017/085158.
Regarding claim 7, Cohen’s notes that the number-average molecular weight (Mn) of the polyester is in the range of 200 to 8000 g/mol (page 7, line 3). Since condensation polymers have typical Mw/Mn ≈ 2, the weight average molecular weight (Mw) range can be determined to be 400 to 16,000 g/mol, which overlap the claimed requirement.
As discussed, when addressing claim 1, Cohen teaches polyester of the inventive example 5 (page 17, lines 5-11), derived from adipic acid and tetrahydrofuran dimethanol, but does not provide its Tg or the molecular weight data. However, Cohen’s polyester is derived from identical monomers as discussed in the specification (adipic acid, specification page 13, line 10; tetrahydrofuran dimethanol, page 17, line 4; page 24, line 10) and generated under similar high temperature polycondensation as the instant specification and therefore would be expected to meet both the claimed Tg and weight average molecular weight.
Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977).
Regarding claims 12 and 15, as discussed when addressing claim 8, Cohen teaches a process where monomers tetrahydrofuran dimethanol (THFDM) and adipic acid, corresponding to Chemical Formula 3 and 4 respectively are reacted together to generate the esterification reaction product (page 17, inventive example 5). Cohen further teaches polycondensation catalysts which can be selected to be titanium based compounds, thus making the claimed requirement obvious (page 5, preparation process, line 40).
Claims 2-4 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Cohen, as applied to claims 1 and 8 above, and further in view of Gao et al. CN 102604052 A.
Regarding claims 2-4 and 9-10, Cohen highlights in the general description of the suitable dicarboxylic acids to be both linear or branched aliphatic dicarboxylic acids having 2 to 20 carbon atoms (page 2, Component A, line 30). Cohen additionally notes succinic acid (page 3, line 1) as an example of an aliphatic dicarboxylic acid. Cohen fails to mention a specific permutation of a suitable branched aliphatic carboxylic acid, thus one of ordinary skill would take guidance from related disclosures to ascertain what might be used in that capacity.
Analogous reference Gao teaches bio-based aliphatic polyesters (para [0008]), which is derived from butanediol and 2-methyl succinic acid (para [0011]). Gao recommends the utilization of branched 2-methylsuccinic acid as a comonomer to prepare the polyester since it provides reduced regularity to the polymer main chain due to the presence of methyl groups, which changes the crystallization properties of the polymer and further regulates its biodegradability (para [0017]). 2-methyl succinic acid meets the claimed requirement, where A13 is C2 aliphatic, with C1 branch (instant claim 2); and -CH2CHR’-, R’ is an alkyl group (of instant claim 3) and where R12 is C1 alkyl group in Chemical Formula 2 (instant claim 4, and instant claims 9-10).
It would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have utilized 2-methyl succinic acid as a suitable branched aliphatic dicarboxylic acid in Cohen’s polyester as taught by Gao for the same application of creating polyester with improved biodegradability.
Claims 1-3 and 7-15 are rejected under 35 U.S.C. 103 as being unpatentable over Jeol WO2016102361A1.
Jeol teaches polyester and the process of preparing the polyester with repeat units derived from polycondensation reaction of 2,5-bis(hydroxymethyl)tetrahydrofuran (tetrahydrofuran dimethanol, THFDM) and at least one compound chosen from aromatic dicarboxylic acids (para [0004]).
Regarding claims 1-3 and 8-12 and 15, Jeol discloses polyester with the repeat unit of general formula (I) as shown below, where R1 is a C6-C24 divalent aromatic group, derived from a dicarboxylic acid which can be chosen to be terephthalic acid (see abstract, and para [0123]).
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Jeol provides the structure of the diol monomer 2,5-bis(hydroxymethyl)tetrahydrofuran (tetrahydrofuran dimethanol, THFDM), as presented below (original, page 5, line 15), which corresponds to applicant’s Chemical Formula 3 (instant claim 8).
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Jeol further discloses (paras [0128]-[0129]) that aliphatic dicarboxylic acids such as 2-methylglutaric acid (instant claims 9-10) can also be utilized as an additional monomer, which meets the claimed requirement of Chemical Formula 4 (instant claim 8), where A13 is branched divalent hydrocarbon, as depicted below.
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An obvious polyester of Jeol would be where both terephthalic acid (aromatic dicarboxylic acid, instant claim 11) and 2-methylglutaric acid are utilized as the dicarboxylic acid monomers along with tetrahydrofuran dimethanol, such a polyester would have portion of repeat units which correspond to the required Chemical Formula 1, with n11>1 and where A13 is a divalent branched aliphatic group -CH2CH2CHR’-(instant claims 1-3).
Jeol teaches the method (instant claim 8) of producing the polyester (paras [0138]-[0139]) where esterification reaction is carried out with 2,5-bis(hydroxymethyl)tetrahydrofuran and one or more dicarboxylic acids, followed by condensation polymerization in the presence of a catalyst such as titanium tetrabutoxide (para [0142]), thus making the claimed requirements obvious (instant claims 12 and 15).
Regarding claim 7, Jeol teaches the polyester glass transition temperature of 50 to 120 oC, overlapping the claimed requirement (para [0052]). Jeol further notes that the number-average molar mass (Mn) is in the range of 5000 to 30,000 g/mol(para [0054]). Since condensation polymers have typical Mw/Mn ≈ 2, the Mw range can be determined to be 10,000 to 60,000g/mol, which overlap the claimed requirement. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claim 13, Jeol teaches (para [0144]), that the esterification is carried out under the pressure range of 1.03-8.16 kg/cm2 (atmospheric pressure to 8 bars) in the temperature range of 200 and 240 oC, meeting the claimed requirements.
Regarding claim 14, Jeol teaches (para [0145]) that polycondensation is carried out under vacuum at a pressure of less than or equal to 1 mbar (0.75mmHg), at a temperature range of 200-260oC, for at least 30 min, which overlap and meet the claimed requirements. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Surbhi M Du whose telephone number is (571)272-9960. The examiner can normally be reached M-F 9:00 am to 5:00pm.
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/S.M.D./
Examiner
Art Unit 1765
/HEIDI R KELLEY/ Supervisory Patent Examiner, Art Unit 1765