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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 11/11/2025 has been entered.
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 1-2, 5-6, 8-10 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Muzanek et al. US 2007/0004856 A1 (provided on IDS dated 01/11/2022).
Regarding claims 1, 5 and 9-10, Muzanek teaches a process to create an aqueous polyurethane dispersion (para [0096]) in Example 16. Muzanek discloses the creation of a blocked polyisocyanate derived from Desmodur VL R 20, which is an aromatic polyisocyanate based on diphenylmethane diisocyanate (para [0070]) and butanone oxime. Muzanek notes that the blocking reaction is carried out until free NCO groups were no longer detected by IR spectroscopy, which indicates a fully blocked polyisocyanate.
Muzanek teaches a process to create a prepolymer where the 28.77 g (28.77g /134.131 gmol-1 = 0.214 mol) of dimethylolpropionic acid was reacted with 107.25 g (107.25g /250 gmol-1 = 0.429 mol) of 4,4’ diisocyanatodiphenylmethane which leads to the required isocyanate groups (0.429/0.214) =2, and molar ratio of NCO:OH of 2:1 (instant claim 5). The dimethylolpropionic acid consists a COOH group. The prepolymer is generated in the presence of a fully blocked polyisocyanate, and meets the requirement of mixture A and corresponds to step a.
Muzanek further teaches the creation of a polyurethane where a polyester polyol derived from adipic acid, isophthalic acid, trimethylolpropane, neopentyl glycol and propylene glycol (instant claims 9 and 10), is reacted with the polyisocyanate (Desmodur VL R 20) in the presence of mixture A, leading to formation of required mixture B (and corresponds to step b). The reaction product is further neutralized by dimethylethanolamine before dilution with deionized water and results in a slightly basic pH which implies 100% neutralization of the acid groups in mixture B.
The invention as claimed is fully anticipated by Muzanek as disclosing each limitation of the rejected claims as per discussion above.
Regarding claims 2 and 20, as discussed when addressing claim 1, Muzanek’s Example 16 (para [0096]) utilizes 4,4’ diisocyanatodiphenylmethane for the creation of prepolymer, where R1 is an aromatic residue. The diol used for the generation of prepolymer of step a is dimethylolpropionic acid, where R2 is aliphatic and contains a COOH group, thus both the diisocyanate and the diol meet the claimed requirements.
Regarding claim 6, the prepolymer of Muzanek’s example 16 (para [0096]) derived from 4,4’ diisocyanatodiphenylmethane and dimethylolpropionic acid, would inherently meet the structural requirement of formula (4).
Regarding claim 8, Muzanek teaches in example 16 (para [0096]) the theoretically possible consumption of isocyanate groups of the 4,4’ diisocyanatodiphenylmethane, corresponding to formula (1) which is calculated to be (100-9.31) = 90.69 mol%, meeting the claimed requirement.
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 3-4 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Muzanek et al. US 2007/0004856 A1.
Regarding claim 3, as discussed when addressing claim 2, Muzanek’s Example 16 (para [0096]) utilizes 4,4’ diisocyanatodiphenylmethane and dimethylolpropionic acid for the creation of prepolymer. The diol’s R2 contains a COOH group. Muzanek teaches (reference claims 1 and 3) that the prepolymer can be generated using hexamethylene diisocyanate (HDI), which meets the R1 with C6 aliphatic carbon atoms. Obvious embodiment of Muzanek’s example 16, would be where 4,4’ diisocyanatodiphenylmethane is substituted with HDI.
Regarding claim 4, Muzanek teaches (reference claims 6 and 7), hydroxyl component 1, 4-butanediol, which meets the requirement of formula (3). Obvious embodiment of Muzanek’s example 16 would be where both diols 1,4- butanediol and dimethylolpropionic acid are utilized for the creation of prepolymer.
Regarding claim 7, Muzanek’s example 16 (para [0096]) teaches the creation of a blocked polyisocyanate derived from Desmodur VL R 20, which is an aromatic polyisocyanate based on diphenylmethane diisocyanate (para [0070]). It is unclear how many NCO groups are present in Desmodur VL R 20. Muzanek however discloses (para [0073]) Desmodur Z 4470 which is an aliphatic polyisocyanate trimer prepared from isophorone diisocyanate which meets the requirement of R4 with m=3. Obvious embodiment of Muzanek’s example 16 would be where Desmodur VL R 20 is substituted with Desmodur Z 4470 for the creation of fully blocked polyisocyanate.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Muzanek et al. US 2007/0004856 A1, as applied to claims 1 and 10, and further in view of Salatin et al US 4,791,168 with evidentiary support reference Vedanayagam et al. (Polymer 1992, 33 (16), 3495-3499).
Regarding claim 11, as discussed when addressing claims 1 and 10, Muzanek teaches the generation of polyester polyols, however Muzanek is silent on the use of a dicarboxylic acid or dicarboxylic acid anhydride conforming to formula (6) or formula (6’) respectively. Muzanek highlights the use of inventive polyurethane-based dispersions for automotive coatings (paras [0004] and [0024]). A skilled artisan would look to analogous art comprising polyester polyols-based polyurethanes utilized for similar coating applications to further optimize the composition.
Reference Salatin also teaches the use of water-borne polyurethanes for automotive coatings (col 2, lines 1-5). Salatin recommends the incorporation of C36 dicarboxylic acid product known as dimer fatty acid which is commercially available as Empol 1010 (col 4, lines 10-16) for the creation of a polyester intermediate. Advantageously, Salatin provides the motivation for incorporating the dimer acid as it provides low flash and quick-drying characteristics to the coating composition due to increased hydrophobicity offered by the dimer acid fraction (col 3, lines 30-36). As evidenced by Vedanayagam C36 dimer acid Empol 1010 meets the structural requirement of R5 corresponding to formula (6), where n linker is C18 and R5 is C34 (Figure 1, page 3497).
It would have been obvious to one of ordinary skilled in the art before the effective filing date of the invention to have incorporated a dimer fatty acid (such as Empol 1010) in the polyester polyol of Muzanek as taught by Salatin for the same application of creating polyurethane coating with low flash and quick-drying characteristics.
Response to Arguments
Applicant's arguments filed on 11/11/2025 have been fully considered, please see the responses below:
Applicant has provided calculations to demonstrate that functionality of the prepolymer of Muzanek’s Example 16 is 1.5 and not 2, and is therefore outside the claimed range.
Applicant has incorporated the blocked polyisocyanate MEKO-MDI adduct as part of the calculations. Applicant’s own specification page 11, last past para, highlights that the blocked polyisocyanates employed in step a do not participate in the reaction forming the prepolymer. Applicant seem to be calculating the NCO content of the whole mixture A, and not the prepolymer which is present in the mixture. Additionally, Page 8, para 6 of the applicant’s remarks indicate that the prepolymer with 2NCO termini are indeed present in the mixture: “Diisocyanates, prepolymers with 2 NCO termini and diisocyanate-DMPA adducts can be present here”. Applicant’s overall calculations are unclear and difficult to understand.
As discussed in the rejection over Muzanek the NCO:OH ratio of 2:1 is expected to produce the prepolymer with an NCO at each end. Thus, applicant’s arguments (and calculations) that Muzanek does not teach the required NCO functionality of the prepolymer are not convincing, and thus the rejection of the claims over Muzanek is maintained.
Conclusion
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/S.M.D./
Examiner
Art Unit 1765
/DAVID J BUTTNER/Primary Examiner, Art Unit 1765 11/19/25