DETAILED ACTION
Notice of Pre-AIA or AIA Status
Claim(s) 1-6, 8-16, 18-19, 24, 28 is/are pending.
Claim(s) 1-6, 8-16, 18-19, 24, 28 is/are rejected.
Claim(s) 7, 17, 20-23, 25-27, 29-31 is/are cancelled by Applicant.
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 .
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 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.
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.
The rejections under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, in the previous Office Action mailed 09/10/2025 have been withdrawn in view of the Claim Amendments filed 12/10/2025.
Claim Rejections - 35 USC § 103 (AIA )
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.
Claim(s) 1-6, 9-16, 18-19, 24, 28 is/are rejected under 35 U.S.C. 103 as being unpatentable over:
• WAMPRECHT ET AL (US 6,423,816),
and in view of MARKUSCH ET AL (US 4,788,262).
WAMPRECHT ET AL ‘816 discloses polyester polyols having:
(1) hydroxyl numbers of from 60-400 mg KOH/g;
(2) acid numbers of 0.5-80 mg KOH/g;
(3) number average molecular weights of 500-10,000;
wherein a preferred embodiment of the polyester polyols is a reaction product of:
(a) 53.5-65.8 equivalent % (wherein (a)+(b) add up to 100%) with an alcohol component comprising:
(a1) 30-100 mol% of aliphatic alcohol having at least 3 hydroxyl groups (e.g., glycerol (containing 3 OH groups), trimethylolpropane (containing 3 OH groups), pentaerythritol (containing 4 OH groups), sorbitol (containing 6 OH groups), etc., and mixtures thereof, etc.) (corresponding to the recited component “(i) a polyol comprising 3 or more hydroxyl groups”);
(a2) optional aliphatic or cycloaliphatic alcohols having two hydroxyl groups, wherein component (a2) is not required (corresponding to the recited “essentially free of a diol”);
(a3) optional aliphatic or cycloaliphatic alcohols having one hydroxyl group, wherein component (a3) is not required;
(b) 34.2 to 46.5 equivalent % (wherein (a)+(b) add up to 100%) of a carboxylic acid component comprising:
(b1) 10-90 mol% of unsaturated dicarboxylic acids (e.g., fumaric acid, maleic acid, itaconic acid, and/or anhydrides thereof, and mixtures thereof) (additionally or alternatively corresponding to the recited component “(ii) a dicarboxylic acid or an anhydride thereof that comprises 3 carbon atoms or fewer between the carboxylic acid groups or the anhydride thereof”);
(b2) up to 80 mol% of aliphatic or cycloaliphatic, saturated or unsaturated dicarboxylic acids having at least 2 carbon atoms and/or their anhydrides different from component (b1) (e.g., oxalic acid, malonic acid, dimethyl malonic acid, succinic acid, glutaric acid, hexahydrophthalic acid, tetrahydrophthalic acid, etc., and/or anhydrides thereof, and mixtures thereof) (additionally or alternatively corresponding to the recited component “(ii) a dicarboxylic acid or an anhydride thereof that comprises 3 carbon atoms or fewer between the carboxylic acid groups or the anhydride thereof”);
(b3) 10-50 mol% of aliphatic or cycloaliphatic, saturated or unsaturated monocarboxylic acids having 1 to 18 carbon atoms (e.g., formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, 2-methylbutanoic acid, 3-methylbutanoic acid, 2,2-dimethylpropionic acid, 2-ethylbutanoic acid, 2-ethylhexanoic acid, octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, etc., and/or anhydrides thereof, and mixtures thereof) (corresponding to the recited component “(iii) a monocarboxylic acid or an anhydride thereof”);
wherein the polyester polyols are useful in curable two-component (2K) polyurethane-type coating composition comprising:
(I) a polyhydroxyl component comprising:
• the disclosed polyester polyols;
• optionally other organic polyhydroxy1 compounds (corresponding to the recited “second hydroxyl functional polymer”) (e.g., other polyester polyols, polyether polyols, polyacrylate polyols, etc.), wherein the other polyhydroxy compounds can comprise up to 90 hydroxyl equivalent %, based on the total weight of the polyhydroxyl component in the coating composition;
(II) a polyisocyanate component (corresponding to the recited “crosslinkers”),
(III) optionally other additives -- for example:
• up to 70 wt% (preferably 50 wt%) of organic solvents;
• other additives (e.g., plasticizers, pigments, fillers, catalysts, stabilizers, etc.);
wherein the curable coating compositions can be applied to various conventional coating substrates (e.g., metal, wood, etc.). (entire document, e.g., line 8-18, col. 1; line 60, col. 1 to line 50, col. 4; line 3-19, col. 5; line 42-50, col. 5; line 62, col. 5 to line 54, col. 6; line 60, col. 6 to line 21, col. 7; line 32-39, col. 7; line 30-37, col. 8; etc.) However the reference does not specifically explicitly disclose molar ratios between polyols (i) + diols (iv) and dicarboxylic acids (ii) + (v) or molar ratios between polyols (i) + diols (iv) and monocarboxylic acid (iii).
MARKUSCH ET AL ‘262 discloses that it is well known in the art to utilize monocarboxylic acids in production of polyester polyols used in curable polyurethane coatings in order to regulate the OH functionality / molecule, which allows the production of polyester polyols with a predetermined functionality value (e.g., 5-15, etc.). The reference further discloses that it is well known in the art in the production of polyester polyols, that the ratio of hydroxyl (OH) groups to carboxylic acid (COOH) groups is typically 4:1 to 1:1. (line 1-59, col. 4; line 4-44, col. 4; etc.)
Regarding claims 1-6, 9-16, 18-19, 24, 28, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to utilize known polyester polyols derived from a combination of polyols, dicarboxylic acids, and monocarboxylic acids as disclosed in WAMPRECHT ET AL ‘816 known coating compositions.
Further regarding claim 1, since WAMPRECHT ET AL ‘816 discloses a polyester polyol derived from: (a) 53.5-65.8 equivalent % of a polyol component comprising up to 30-100 mol% of a polyol (a1) having at least 3 hydroxyl groups; and (b) 34.2 to 46.5 equivalent % comprising 50-90 mol% combined dicarboxylic acid component(s) (b1)+(b2) and 10-50 mol% monocarboxylic acid component; the polyester polyols of WAMPRECHT ET AL ‘816 have polyol (a1) : dicarboxylic acid (b1+b2) molar ratios and polyol (a1) : (iii) monocarboxylic acid (b3) ratios which at least partially read on the claimed “(i) to (ii) + (iv) ranges from 1.08:1 to 1.75:1” and “(i) + (iv) to (iii) ranges from 1.25:1 to 4:1”. For example, but not limited to: for a polyester polyol derived from:
(i) 3 moles of polyol (a1) x (3 OH eq/mole) = 9 OH molar eq
(ii) 2 moles of dicarboxylic acid (b1)+(b2) x (2 COOH eq/mole) = 4 COOH molar eq
(iii) 1 mole of monocarboxylic acid (b3) x (1 COOH eq/mole) = 1 COOH molar eq
(i) to (ii) molar ratio of 1.5:1 (3:2)
(i) to (iii) molar ratio of 3:1
equivalent% (a) = 64.3% [100 mol% (a1)]
equivalent% (b) = 35.7% [67 mol% (b1+b2) + 33 mol% (b3)]
Further regarding claim 1, it would have been obvious to one of ordinary skill in the art to utilize select the ratio of polyols to monocarboxylic acids to produce the polyester polyols of WAMPRECHT ET AL ‘816 in order to form polyester polyols suitable for forming curable coating compositions with tailored hydroxy functionality values typically used in curable coating compositions (as suggested in MARKUSCH ET AL ‘262).
Regarding claims 2-3, trimethylolpropane, which can be used as component (a) of WAMPRECHT ET AL ‘816, has three OH groups and a molecular weight of about 134 g/mol.
Regarding claim 4, hexahydrophthalic acid and phthalic acid, which can be used as a portion of component (b) of WAMPRECHT ET AL ‘816, contain aromatic structures (corresponding to the recited “cyclic content”).
Regarding claim 10, one of ordinary skill in the art would have selected the molecular weight (as represented by the intrinsic viscosity) of the polyester polyols of WAMPRECHT ET AL ‘816 in order to adjust the viscosity of coating compositions containing said polyester polyols and/or to optimize the physical properties (e.g., hardness, flexibility, etc.) of the resulting cured compositions for specific applications.
Regarding claims 11-12, one of ordinary skill in the art would have selected the amount of branching points (and thereby the number of OH terminal group per molecule) in the polyester polyols of WAMPRECHT ET AL ‘816 in order to control the crosslinking density of the resulting cured coating derived from said polyester polyols.
Regarding claims 16, 18, since WAMPRECHT ET AL ‘816 discloses that the polyhydroxyl component of curable coating compositions can comprising: (1) at least 10 hydroxyl equivalent % of the disclosed polyester polyols; and (2) up to 90 hydroxyl equivalent % of other organic polyhydroxy1 compounds (corresponding to the recited “second hydroxyl functional polymer”) (e.g., other polyester polyols, polyether polyols, polyacrylate polyols, etc.); curable coating compositions in accordance with WAMPRECHT ET AL ‘816 can contain weight ratios of the polyester polyol and the other polyhydroxyl compound which at least partially read on the recited weight ratio range recited in claim 18. For example, for an additional polyhydroxyl compound with the same OH equivalents/mole and substantially similar molecular weights, curable compositions in accordance with WAMPRECHT ET AL ‘816 can contain weight ratios of WAMPRECHT ET AL ‘816 polyester polyol to additional polyhydroxyl compound of about 10:0 to 1:9.
Additionally and/or alternatively, regarding claim 18, one of ordinary skill in the art would have selected the weight ratio of polyester polyols in accordance with WAMPRECHT ET AL ‘816 to other optional polyhydroxyl compounds in the coating compositions of WAMPRECHT ET AL ‘816 in order to obtain the desired curing characteristics and physical properties in the resulting cured coating.
Regarding claim 19, since WAMPRECHT ET AL ‘816 discloses coating compositions containing at most 70 wt% (preferably, at most 50 wt%) solvent, the reference discloses coating compositions containing 30 wt% or more (preferably 50 wt% or more) of solids.
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over:
• WAMPRECHT ET AL (US 6,423,816), and in view of MARKUSCH ET AL (US 4,788,262),
as applied to claim 1 above,
and further in view of RAMESH (US 2002/0026015).
RAMESH ‘015 discloses that it is well known in the art to incorporate carbamate functional groups in polyester polyols in order to enhance the formation of urethane structures in polyurethane-type curable coatings. (paragraph 0034, 0057-0064, etc.)
Regarding claim 8, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to incorporate carbamate functional groups as suggested in RAMESH ‘015 in the polyester polyols of WAMPRECHT ET AL ‘816 in order to aid the formation of polyurethane-type coatings.
Claim(s) 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over:
• WAMPRECHT ET AL (US 6,423,816), and in view of MARKUSCH ET AL (US 4,788,262),
as applied to claim 1 above,
and further in view of SRINIVAS ET AL (US 2013/0331542). SRINIVAS ET AL ‘542 discloses that it is well known in the art to produce polyester polyols with relatively low viscosities (e.g., 0.02-0.1 dL/g or 2-10 mL/g) in order to facilitate the formation of lower viscosity coating compositions. (paragraph 0021, etc.)
Regarding claim 10, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use known methods to produce the polyester polyols of WAMPRECHT ET AL ‘816 with relatively low viscosity (e.g., 8 mL/g) as suggested in SRINIVAS ET AL ‘542 in order to facilitate the production of lower viscosity coating compositions which can be more readily applied by known coating methods and avoid undesirable gelling.
* * *
The rejections under 35 U.S.C. 103 based on HABERECHT ET AL (US 2011/0257329) in the previous Office Action mailed 09/10/2025 have been withdrawn in view of the new grounds of rejection necessitated by the Claim Amendments filed 12/10/2025.
Response to Arguments
Applicant’s arguments filed 12/10/2025 with respect to the rejections under 35 U.S.C. 103 based on DOS SANTOS (US 6,184,332) or HABERECHT ET AL (US 2011/0257329) in the previous Office Action mailed 09/10/2025 have been considered but are moot because the new grounds of rejection necessitated by the Claim Amendments filed 12/10/2025.
(A) The Examiner notes that the newly added phrase “all of the components are used in the reaction to form the polyester polyol” in present claim 1 does not exclude the use of a multi-step or multi-stage reaction to produce the recited polyester polyol, and therefore present claim 1 does not preclude components (i)-(iv) from being used in different steps or stages of a multi-step or multi-stage reaction used to produce the polyester polyol.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
ALTOUNIAN (US 6,525,162) disclose polyester polyols for coatings.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Vivian Chen (Vivian.chen@uspto.gov) whose telephone number is (571) 272-1506. The examiner can normally be reached on Monday through Thursday from 8:30 AM to 6 PM. The examiner can also be reached on alternate Fridays.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Callie Shosho, can be reached on (571) 272-1123. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300.
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March 25, 2026
/Vivian Chen/
Primary Examiner, Art Unit 1787
Prosecution Insights