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 Objections
Claims 7, 13 – 15, and 18 are objected to because of the following informalities:
Claim 7 should be amended to recite “1,4-butanediol”;
units for molecular weight should be inserted in Claims 13 – 15; and
2,6 should appear in superscript in each instance in Claim 18.
Applicant is additionally advised that should Claim 4 be found allowable, Claim 6 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 19 and 20 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
New Claims 19 and 20 set forth the dicarboxylic acid component (A) comprise no more than respectively 10.0% and 5.0% mass percent of a further dicarboxylic acid. However, it is unclear how the dicarboxylic acid component (A) could comprise a further dicarboxylic acid at an upper limit of either 10.0% or 5.0% mass percent. Claim 1 sets forth dicarboxylic acid (a1) is present at a minimum of 97.0 mass% and dicarboxylic acid (a2) is present at a minimum of 0.02 mass%. Thus, a further dicarboxylic acid could only possibly be present in an amount of up to 2.98 mass%. For the purposes of further examination, Claims 19 and 20 will then be interpreted as requiring further dicarboxylic acid could only possibly present in an amount of less than 2.98 mass% dicarboxylic acid component (A).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1 – 9, 13 – 17, 19, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over JPS6026018 to Matsumoto et al. (hereinafter Matsumoto) in view of US 2004/0116619 to Moad et al. (hereinafter Moad). For the purposes of examination, citations for Matsumoto are taken from a machine translation of the document obtained from the European Patent Office in March 2026.
Regarding Claims 1, 3, 8, 9, 19, and 20. Matsumoto teaches a polyester polyol obtained by reacting a dicarboxylic acid mixture and a glycol/diol component (see Lines 16 – 19 of Page 1 of the machine translation).
The dicarboxylic acid mixture comprises 3-methylpentanedioc acid (see Lines 19 – 22 of Page 1 of the machine translation), which is alternatively known in the art as 3-methylglutaric acid. As detailed in the instant specification, 3-methylglutaric acid corresponds to a dicarboxylic acid of general formula (I) in which R1 and R2 are each a methylene/linear group and R3 is a methyl group (see [0027] of the PG-PUB of the instant application), i.e. a monovalent hydrocarbon group having one carbon atom.
Matsumoto teaches the dicarboxylic acid mixture comprises more particularly at least 40% by weight or more of the 3-methylpentanedioc acid (see Lines 10 – 12 of Page 1 of the machine translation). The remainder of the dicarboxylic acid mixture, greater than 0 to less than 60% by weight thereof, would thus correspond to a dicarboxylic acid other than 3-methylpentanedioc acid. While this range is not identical to the instantly claimed range for the dicarboxylic acid (a2) of 0.02 to 3.00% by mass in 100% by mass of the total amount of the dicarboxylic acid component, it does overlap. It has been held that 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, 191 USPG 90 (CCPA 1976) (MPEP 2144.05)
Matsumoto does not expressly teach the dicarboxylic acid other than 3-methylpentanedioc acid corresponds to a compound which may be represented by instantly claimed general formula (II). However, Moad teaches the concept of providing the dicarboxylic acid, 3-hydroxy-3-methyl glutaric acid, in the preparation of a polyester polyol [0036]. As detailed in the instant specification, 3-hydroxy-3-methyl glutaric acid corresponds to a dicarboxylic acid of general formula (II) in which R4 and R5 are each a methylene group and R6 is a methyl group (see [0036] of the PG-PUB of the instant application). Matsumoto and Moad are analogous art as they are from the same field of endeavor, namely polyester polyols obtained by reacting dicarboxylic acid and diol components. Before the effective filing date of the instantly claimed invention, it would have been obvious to a person of ordinary skill in the art to provide 3-hydroxy-3-methyl glutaric acid as the dicarboxylic acid other than 3-methylpentanedioc acid in Matsumoto. The dicarboxylic acid component would then consist of 3-methylpentanedioc acid and 3-hydroxy-3-methyl glutaric acid and comprise 0 mass% of a further dicarboxylic acid. The motivation would have been that Moad teaches that 3-hydroxy-3-methyl glutaric acid will introduce branching in the polyester polyol [0036]. Branching in the polyester polyol would be provide benefits, such as increasing the cross-linking density and improving the mechanical properties of the products prepared therefrom.
Regarding Claim 2. Matsumoto teaches a polyester polyol of Claim 1. As detailed in the rejection of Claim 1 above, Matsumoto teaches the dicarboxylic acid mixture comprises more particularly at least 40% by weight or more of the 3-methylpentanedioc acid (see Lines 10 – 12 of Page 1 of the machine translation). The remainder of the dicarboxylic acid mixture, greater than 0 to less than 60% by weight, would thus correspond to a dicarboxylic acid other than 3-methylpentanedioc acid.
This amount can be alternatively expressed as a content of dicarboxylic acid component (a2) of greater than 0 to 150 parts by mass with respect to 100 parts by mass of the dicarboxylic acid component (a1). While this range is not identical to the instantly claimed range for the dicarboxylic acid (a2) of 3.00 parts by mass or less with respect to 100 parts by mass of the dicarboxylic acid component (a1), it does overlap. It has been held that 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, 191 USPG 90 (CCPA 1976) (MPEP 2144.05)
Regarding Claims 4 and 6. Matsumoto teaches a urethane prepolymer obtained by reacting the polyester polyol of Claim 1 with a polyisocyanate compound (see final two lines of Page 2 – first four lines of Page 3 of the machine translation).
Regarding Claim 5. Matsumoto teaches a polyurethane made from the polyester polyol of Claim 1 (see Lines 16 – 20 of Page 1 of the machine translation).
Regarding Claim 7. Matsumoto teaches the polyester polyol of Claim 1, wherein the glycol/diol component may comprise ethylene glycol or propylene glycol (see Line 27 of Page 1 of the machine translation).
Regarding Claims 13 – 15. Matsumoto teaches the polyester polyol of Claim 1 having a molecular weight of 300 to 10,000 (see Lines 16 – 18 of Page 1 of the machine translation).
Regarding Claims 16 and 17. Matsumoto teaches the polyester polyol of Claim 1 is prepared from a glycol initiator (see Lines 16 – 19 of Page 1 of the machine translation), i.e. an initiator having two hydroxyl groups. The obtained polyester polyol would then be reasonably expected to also have two hydroxyl groups per molecule.
Claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over JPS6026018 to Matsumoto et al. (hereinafter Matsumoto) in view of US 2004/0116619 to Moad et al. (hereinafter Moad), as applied to Claim 1 above, and further in view of US 2009/0253858 to Argyropoulos et al. (hereinafter Argyropoulos). For the purposes of examination, citations for Matsumoto are taken from a machine translation of the document obtained from the European Patent Office in March 2026.
Regarding Claim 18. Matsumoto teaches the polyester polyol of Claim 1, but does not expressly teach the glycol/diol component comprises one of the instantly claimed compounds. However, Argyropoulos teaches the concept of providing a mixture of cyclohexanedimethanol isomers as the diol component in the preparation of a polyester polyol [0013]. Matsumoto and Argyropoulos are analogous art as they are from the same field of endeavor, namely polyester polyols and polyurethanes prepared therefrom. Before the effective filing date of the instantly claimed invention, it would have been obvious to provide a mixture of cyclohexanedimethanol isomers as taught by Argyropoulos as the diol component in the preparation of the polyester polyol of Matsumoto. The motivation would have been that Argyropoulos teaches that the use of this mixture provides polyurethane polymers having good hydrolytic and acid resistance [0013].
Allowable Subject Matter
Claims 10 – 12 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: the prior art does not teach or suggest a polyester polyol comprising all of the instantly claimed ingredients in the claimed amounts including a dicarboxylic acid (a1) of instantly claimed formula (I) in which R1 and/or R2 are branched; comprise a halogen atom as a substituent; or comprise a hydroxy group as a substituent.
JPS6026018 to Matsumoto et al. corresponds to the closest prior art. Matsumoto teaches a polyester polyol obtained by reacting a dicarboxylic acid mixture and a glycol/diol component (see Lines 16 – 19 of Page 1 of the machine translation).
The dicarboxylic acid mixture comprises 3-methylpentanedioc acid (see Lines 19 – 22 of Page 1 of the machine translation), which is alternatively known in the art as 3-methylglutaric acid. As detailed in the instant specification, 3-methylglutaric acid corresponds to a dicarboxylic acid of general formula (I) in which R1 and R2 are each a methylene/linear group (see [0027] of the PG-PUB of the instant application), i.e. a monovalent hydrocarbon group having one carbon atom. Thus, the groups corresponding to R1 and R2 in the dicarboxylic acid of Matsumoto are not branched hydrocarbons and are free of both halogen and hydroxyl group substituents. Additionally, no other prior art reference provides any teaching or guidance which would lead a person of ordinary skill in the art to modify the groups corresponding to R1 and R2 in the manner necessary to arrive at the instantly claimed formula set forth in Claims 10, 11, and 12.
Response to Arguments
Applicant's arguments filed June 18, 2026 have been fully considered but they are not persuasive.
Applicant argues that the present application proves that a particular, small amount of 0.02 to 3.00 mass% of 3-hydroxyl-3-methylglutaric acid can reduce the viscosity of a urethane prepolymer while maintaining hydrolysis resistance. Applicant cites [0039] of the PG-PUB of the instant application, which provides a discussion of the reason for selecting a content of dicarboxylic acid (a2) in the aforementioned range. Applicant additionally cites Table 2 of the instant application as demonstrating criticality of the claimed amount of dicarboxylic acid (a2).
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980) The Office respectfully submits that the provided evidence is not commensurate in scope with the instant claims, as it tests only one species each of dicarboxylic acid (a1) (MGA) and dicarboxylic acid (a2) (HMGA). On the other hand, instantly claimed dicarboxylic acids (a1) and (a2) may each correspond to a sizeable number of compounds and an even greater number of possible combinations thereof.
Furthermore, to establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960). The Office respectfully submits that Table 2 of the instant specification does not compare a sufficient number of tests inside and outside the claimed range of 0.02 to 3.00 mass% of dicarboxylic acid (a2). The inventive examples inside the claimed range only test amounts of dicarboxylic acid (a2) of 0.15 to 1.28 weight percent, whereas the comparative examples outside the claimed range only test amounts of dicarboxylic acid (a2) of 0.01 weight percent. The data provided is then insufficient to show the criticality of the claimed range of dicarboxylic acid (a2).
In response to applicant’s argument that Moad merely lists 3-hydroxyl-3-methylglutaric acid among numerous other compounds, the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See also In re Leshin, 277 F.2d 197, 125 USPQ 416 (CCPA 1960) (selection of a known plastic to make a container of a type made of plastics prior to the invention was held to be obvious). In the instant case, Moad shows that 3-hydroxyl-3-methylglutaric acid is known in the art as a suitable dicarboxylic acid for the preparation of polyesters, thus providing obviousness in the selection thereof.
In response to applicant's argument that Moad does not recognize the viscosity-reducing effect of 3-hydroxy-3-methyglutaric acid or that its incorporation would have maintained the color quality of Matsumoto, the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). Primary reference Matsumoto allows for the incorporation of dicarboxylic acids other than 3-methylpentanedioc acid in an amounts of roughly up to 60 weight percent and places no particular limitation on the additional dicarboxylic acids which may be provided. Further, Moad shows that 3-hydroxyl-3-methylglutaric acid is known in the art as a suitable dicarboxylic acid for the preparation of polyesters. As such, the Office maintains that there is a reasonable expectation of success in the proposed combination of Matsumoto with Moad and therefore the advantages observed by applicant would flow naturally from said combination of references.
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.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MELISSA RIOJA whose telephone number is (571)270-3305. The examiner can normally be reached Monday - Friday 10:00 am - 6:30 pm EST.
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/MELISSA A RIOJA/ Primary Examiner, Art Unit 1764
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