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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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 19-26, and 29 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jeol, S. WO2016102361A1.
Regarding claims 19, 21-24, Jeol teaches a polyester polymer that is derived from the reaction of the diol 2,5-bis(hydroxymethyl)tetrahydrofuran with dimethyl terephthalate, see example 3 ¶[0244] and example 4 ¶[0250]. The 2,5-BHMTHF reads on B2a and B2a1 of claims 19, 21-22; and the DMT, which is a diester derivative of terephthalic acid, reads on component A1 of claim 19.
A polyalcohol with at least three OH groups and no COOH groups can also be included with the diols, ¶[0135], which reads on optional B1 of claims 19 and 23-24. Jeol further teaches that an additional diol with no COOH groups can be included with the 2,5-BHMTHF, ¶[0130], which reads on the optional B3 of claim 19.
Jeol’s polyester reads on the claimed polyester polyol insofar as it is a polyester formed from the polycondensation reaction of the claimed OH and COOH functional components and with an excess of diol, which is preferable ¶[0254], and is characteristic of polyester polyols with OH end groups.
Regarding claim 20, Jeol teaches that the dicarboxylic acid or diester thereof can further include aliphatic dicarboxylic acids, ¶¶[0128-0129].
Regarding claim 25, Jeol teaches the diols and polyalcohols that read on applicant’s B1, B2, and B3. The ratio of the OH groups with all three present would be 3/(3+2+2) = 3/7 = 42.86%, where B1 is a triol, which falls within the claimed range. Additionally, because B3 is optional, the ratio without B3 would be 3/5= 60%, where B1 is a triol, which also falls within the range.
Regarding claim 26, Jeol reacts the diol with the diester in a ratio of 57.4 mmol to 51.0 mmol for examples 3 ¶[0244] and 48.4 mmol to 48.2 mmol for example 4 ¶[0250]. The diester can be replaced by the dicarboxylic acid version of it ¶[0004], in which case the ratio of OH/COOH would be 57.4/51 = 1.12 for example 3 and 48.4/48.2 = 1.07, both of which fall within the claimed range.
Regarding claim 29, Jeol teaches the number average molecular weight for the polyester of example 4 is 3,870 g/mol, ¶[0253], which is within the claimed range.
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.
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 19-32, 34-36 are rejected under 35 U.S.C. 103 as being unpatentable over Cohen et al, WO2016071245A1.
Regarding claims 19-24, Cohen teaches a polyester polyol that is derived from at least one polyhydric alcohol A and at least one dicarboxylic acid D, ¶[0002]. The dicarboxylic acid is selected from sebacic acid, azelaic acid, dodecanedioic acid and succinic acid, ¶[0028], which are all aliphatic dicarboxylic acids with two COOH groups, and satisfy the component A and A1 of claims 19 and 20.
The polyhydric alcohol A is obtained from renewable raw materials and can be selected as tetrahydrofurandimethanol, ¶[0023], which is another name for 2,5-bis(hydroxymethyl)tetrahydrofuran, and reads on the compound of formula B2a and B2a1 of claims 19, 21, and 22. It would be obvious to select the 2,5-BHMTHF because it is a diol obtained from renewable raw materials and is suitable for use in forming a polyester polyol to be used in a polyurethane dispersion, as taught by Cohen.
The polyester polyol can comprise a mixture of polyhydric alcohols which can further include tri-functional alcohols, such as glycerin and trimethylolpropane, ¶[0026], which reads on the optional compound with three OH groups and no COOH groups, B1, of claims 19 and 23-24. Cohen further teaches that oligomeric or polymeric products with at least two hydroxy groups can also be included in the polyhydric alcohol component, these include polytetrahydrofuran and polyetherols, ¶[0026], which read on the optional compound with two OH groups and no COOH groups, B2, of claim 19.
The fact that Cohen discloses numerous types of polyhydric alcohols which can be suitably selected to form a polyester polyol does not render any particular combination of dicarboxylic acid with the disclosed polyhydric alcohols any less obvious. A reference is available for all that it teaches to a person of ordinary skill in the art. Merck & Co., Inc. v. Biocraft Laboratories, Inc. 874 F.2d 804, 807 (Fed. Cir. 1989).
Regarding claim 25, Cohen teaches the addition of the trifunctional polyalcohols, listed above, which read on applicant’s B1, the 2,5-BHMTHF, which reads on applicant’s B2a1, and the polymeric diols that read on applicant’s B3, ¶¶[0023,0026]. The molar ratio of hydroxyl groups of B1 to the sum of the OH groups in B1, B2, and B3 is 3/(3+2+2) = 3/7 = 42.86%, which falls within the claimed range. Additionally, the component B3 is optional according to claim 19, therefore if only the trifunctional B1 and the difunctional B2 are present, the ratio would then be 3/(3+2) = 3/5 = 60%, which also falls within the claimed range.
Regarding claim 26, Cohen teaches the polyester polyol requires at least one dicarboxylic acid and at least one polyhydric alcohol, ¶[0002], the polyhydric alcohol is preferably a diol, ¶[0019]. The only required components of claim 19 are one dicarboxylic acid, A1, and the diol B2, which Cohen teaches as the 2,5-BHMTHF ¶[0023]. Therefore the minimum ratio of the OH groups of the diol to the COOH groups of the dicarboxylic acids is 2/2 = 1/1. With the presence of a trifunctional alcohol, applicant’s B1, the total OH/COOH ratio is 5/2 = 2.5/1 which falls within the claimed range. Furthermore, Cohen teaches that the dicarboxylic acid component is preferably a mixture of two, ¶[0027], which would put the ratio with polyalcohols B1 and B2 at 5/(2+2) = 5/4 = 1.25/1, which also falls within the claimed range. Also, if the additional polymer diol is present in the polyester polyol, applicant’s B3, then the ratio is 7/2 = 3.5/1 for one dicarboxylic acid (outside of the claimed range) and 7/4 = 1.75/1 for two dicarboxylic acids, which falls within the claimed range.
Therefore, Cohen’s ratio of OH groups to COOH groups for the polyester polyol encompasses the claimed range. 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. 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, 191 USPQ 90 (CCPA 1976).
Regarding claim 27, Cohen teaches the hydroxyl number for the polyester polyol is in the range of 25-230 mg/KOH/g, ¶[0018], which overlaps with the claimed range.
Regarding claim 28, Cohen teaches the claimed polyester polyol with a hydroxyl number that overlaps with the claimed range, and a molecular weight that overlaps with the claimed range. One of ordinary skill in the art is reasonably suggested that the polyester polyol must inherently have an acid number as claimed.
Regarding claims 29-30, Cohen teaches that the molecular weight of the polyester polyol is in the range of 500-4,000 g/mol, ¶[0017], which overlaps with both the claimed Mn and Mw range.
Regarding claim 31, Cohen teaches the polyester polyol is used in a polyurethane dispersion which comprises up to 30 wt.% organic solvent, ¶¶[0074, 0148-0149].
Regarding claim 32, Cohen teaches a coating composition, in example 1, comprising the polyester polyol and an additional diol, which are mixed in a solvent, acetone, and with a catalyst, ¶[0158]. Then the mixture of isophorone diisocyanate and dicyclohexylmethane diisocyanate are added, with more acetone following the mixing, ¶0158]. The resulting mixture is then dispersed in water, ¶[0160]. Cohen does not explicitly teach that the coating composition is a two-component system, but it would be obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to separate the coating composition into two parts, the first part (i) comprising the polyester polyol, additional diol, catalyst, and solvent and the second part (ii) comprising the diisocyanate mixture, with the motivation of preventing premature polymerization or crosslinking of the components until such time as they are ready to be used.
Regarding claim 34, Cohen teaches that the coating composition comprises organic solvent, ¶¶[0074, 0148-0149], catalysts ¶[0137], pigments and other auxiliary ingredients, ¶[0068].
Regarding claims 35-36, Cohen teaches that the PUD composition comprising the polyester polyol is for coating substrates such as wood, paper, cardboard, textiles, and plastics, among others, ¶[0150]. Cohen exemplifies using the PUD of the examples in a coating for leather, ¶[0170].
Claims 19-28, 30-36 are rejected under 35 U.S.C. 103 as being unpatentable over Persson et al, WO2012005647A1.
Regarding claims 19-24, Persson teaches a branched polyester obtained from the reaction of a dicarboxylic acid comprising at least one furandicarboxylic acid A, a diol B, and a branching component having at least three reactive groups C, abstract. Persson teaches the polyester is for use in polyurethane coatings, pg. 1 first para. Then also explains the polyurethane polymers comprise hydroxyfunctional polyesters such as the polyester of the disclosure, pg. 2 second para. This suggests the branched polyester of Persson is in fact a polyester polyol, to be used in a reaction for forming polyurethanes in coatings, which reads on the polyester polyol of claim 19.
Persson further teaches the dicarboxylic acid component A comprises furandicarboxylic acid, bottom pg. 2 to top pg. 3, which reads on the component A of claims 19 and 20. Persson’s component A can further comprise aliphatic or other cycloaliphatic dicarboxylic acids, pg. 3 third para.
The diol component B can be selected as di(hydroxymethyltetrahydrofuran), pg. 3 fourth para., and is listed among the preferred diols in the bottom half of the fourth para. This reads on component B2a and B2a1 of claims 19, 21-22. It would be obvious to the skilled artisan to select the claimed di(hydroxymethyltetrahydrofuran) because it is a preferred diol as taught by Persson.
Also listed in the fourth para. are additional diols such as ethylene glycol and polyether diols, among others, which reads on the optional diol B3 with no COOH groups of claim 19.
Persson further teaches a branching agent, C, that is a triol or polyol that can be selected from polyols that are a 2-hydroxyalkyl-1,3-propanediol, such as specifically trimethylolpropanediol, among others, listed in the fifth para. of pg. 3 to first para. of pg. 4, the trifunctional branching agent reads on the optional component B1 of claims 19, 23-24.
The fact that Persson discloses numerous types of diols which can be suitably selected to form the branched polyester does not render any particular combination of diol with dicarboxylic acid any less obvious. A reference is available for all that it teaches to a person of ordinary skill in the art. Merck & Co., Inc. v. Biocraft Laboratories, Inc. 874 F.2d 804, 807 (Fed. Cir. 1989).
Regarding claim 25, Persson teaches claimed di(hydroxymethyltetrahydrofuran) (BHMTHF) as B2, the optional triol for B1, and optional additional diol for B3, therefore the molar ratio of OH groups is 3/7 = 42.85% which falls within the claimed range. Additionally, if only the B2 diol is present and the optional B3 is not, then the ratio would be 3/5 = 60%, which is also within the range.
Regarding claim 26, Persson teaches the branched polyester must have at least one dicarboxylic acid, one diol, and one triol (or higher) as the branching agent, abstract. Therefore the ratio of OH/COOH groups would be 5/2 = 2.5/1, which falls within the claimed range.
Regarding claims 27, 28 and 30, Persson teaches example 3 has a hydroxyl number of 145 mg KOH/g, an acid value 1.8 mg KOH/g and the weight average molecular weight, Mw, is 2,200 g/mol, pg. 7, which fall within the claimed ranges.
Example 3 does not use the claimed diol of BHMTHF as component B2, but it would be obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to substitute the neopentyl glycol for the claimed BHMTHF diol and obtain the hydroxyl numbers of 145 mgKOH/g an acid value of 1.8 mg KOH/g, and obtain a molecular weight of 2,200 g/mol with the motivation of obtaining another permutation of a branched polyester for use in polyurethane coatings.
Regarding claim 31, Persson teaches in example 3, pg. 7, that the solvent butyl acetate is added to the branched polyester.
Regarding claims 32-36, Persson teaches the branched polyester is useful in 2-K polyurethane coatings, pg. 5 fourth paragraph, and uses the branched polyester of example 3 in a two-component coating formulation on page 8. The formulation has the branched polyester of example 3 milled with pigment and BYK additives (component i), and then the isocyanate HDT is added last (component ii) before being coated on glass and steel panels and thermally cured. The coating on glass and steel reads on the coating layer and substrate of claims 35 and 36.
The example 3 polyester was dispersed in butyl acetate at 55% solids, first para. of pg. 7, so it already has solvent in it when it is used in the 2-K coating formulation. It also has titanium dioxide pigment, BYK additives, Aerosil 200 fumed silica, and while the example does not have additional catalysts, it is disclosed on pg. 2 second para. that additives such as catalysts are used in the polyurethane polymers, all of which read on the additives of claim 34.
Persson does not include an additional polymer with more than one OH group, claimed component D, in the example, but discloses that the branched polyester can be mixed other polymer materials, such as acrylics, in the coating formulations, pg. 2 first para. and third para., which renders obvious the addition of a (meth)acrylic polymer with more than one OH group to the 2-K coating of claim 33.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to VIRGINIA L STONEHOCKER whose telephone number is (571)272-3431. The examiner can normally be reached Monday-Friday 7:00AM-4:00PM EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/V.L.S./Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766