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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 11/19/2025 has been entered.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Status of Claims
The examiner acknowledges the amendments made to claims 1 and 4. Claims 1-15 are pending.
Claim Interpretation
Claim 1 is being examined as a product-by process claim because the claim language is directed toward a linear polymer that places conditions upon its preparation. As such, the patentability is determined solely upon the product and does not depend upon the method of manufacture. See MPEP 2113.I.
Claim Rejections - 35 USC § 112
The applicant has amended claim 4. As a result, the previous 112(d) rejection of this claim is withdrawn.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-11 are rejected under 35 U.S.C. 103 as being unpatentable over Rosenberg (US 20030065124) as evidenced by Rosenberg (US 5,703,193).
Regarding Claims 1 and 4,
Rosenberg (‘124) teaches a polyurethane prepolymer with a molar ratio of NCO:OH in a range of 3:1 to 20:1, but more preferably 5:1 to 10:1 (Paragraph 59) in which the excess isocyanate is removed by distillation such that the residual MDI content is below 0.3% (Paragraph 66). While Rosenberg requires solvent for the distillation, as the claim is a product-by-process claim, because the product obtained would be the same and because in product-by-process claims the product determines patentability, the requirements of the instant claim are met. Rosenberg also teaches the use of MDI monomer (Paragraph 57). Rosenberg teaches that polyether polyols are typically in the molecular weight range of 250 to 6000 Da (Paragraph 58), but does not teach polyols that would have molecular weights that would result in hydroxyl numbers between 6 and 14 mg KOH/g. However, Rosenberg (‘124) does not teach away from the use of such polyols and further references Rosenberg (‘193) (Paragraph 66) which teaches a similar method of monomeric isocyanate removal in which the polyols may be as high as 10,000 molecular weight (Column 4, Lines 56-65) and with a preferred hydroxyl functionality of 2 to 2.5 (Column 5, Lines 7-9). One of ordinary skill in the art would recognize that because both Rosenberg references teach similar polymers using similar methods, that the higher molecular weight polyol would be useable in the composition taught by Rosenberg (‘124) and it would therefore have been obvious to one of ordinary skill in the art to use polyols up to 10,000 molecular weight. A 10,000 Da polymer that is a diol would have an OH number of 11, which meets the requirements of the instant claim.
Rosenberg also does not explicitly teach a prepolymer with isocyanate content of 0.3 to 1.5% by weight, however Rosenberg does state that ratios of isocyanate to hydroxyl group within the preferred range primarily comprises prepolymer that consists of MDI-polyol-MDI. From this, based upon the use of a diol with MW of 6000, a molecular weight of the prepolymer containing two MDI units would be 6500, resulting in an isocyanate content of 1.3%, which when using the appropriate molecular weight polyol falls within the range of the instant claim.
Regarding Claim 2,
Rosenberg teaches the use of monomeric diphenylmethane 4,4’-diisocyanate to generate polyurethane prepolymers (Abstract).
Regarding Claim 3,
Rosenberg teaches the use of polypropylene glycol polyol (Paragraph 75).
Regarding Claim 5,
Rosenberg describes the use of multiple distillations to remove excess MDI from the prepolymer (Paragraph 27), noting that often only a single distillation is required to obtain 0.3% by weight monomeric isocyanate in the prepolymer.
Regarding Claim 6,
Rosenberg teaches obtaining residual monomeric diisocyanate content of less than 0.3% by weight through distillation (Paragraph 24). With regard to the isocyanate content, this is addressed above in regard to claim 1.
Regarding Claim 7,
Rosenberg demonstrates isocyanate content of 93% of theoretical (Example 13, Paragraph 109). While this was demonstrated using a lower molecular weight polyol, the reactivity of macromolecular polyols would be expected to be broadly similar according to Flory’s principle of equal reactivity. As noted above in regard to claim 1, a large excess of isocyanate leads primarily to the formation of isocyanate-polyol-isocyanate compounds, and as such, the excess of isocyanate is driving the reaction to higher theoretical conversion and it necessarily follows to higher theoretical incorporation of isocyanate into the prepolymer. As such, it would have been obvious to have set the isocyanate incorporation to a high level.
Regarding Claim 8,
Rosenberg demonstrates monomeric diisocyanate levels below 0.1% in several examples of Table 1. Additionally, Rosenberg teaches that water may be used as a chain extender (Paragraph 67). Because of this disclosure, while Rosenberg does not explicitly state that the composition is moisture curable, a curing reaction using water can occur, rendering the composition moisture curable.
Regarding Claims 9 and 10,
Rosenberg teaches that polyurethane elastomers can be made by methods known in the art (Paragraph 71), which would include prepolymer incorporation percentages in the disclosed range. Additionally, in the absence of a demonstration of the criticality of this parameter, it would have been obvious to have made a composition that contained prepolymer in the range of the instant claim. See MPEP 2144.5.II.
Regarding Claim 11,
Rosenberg teaches that polyurethane elastomers can be made by methods known in the art (Paragraph 71). The use of higher order isocyanates is common in the art to increase cross-linking in the resulting cured material. One of ordinary skill in the art would be motivated to increase the cross-linking density to improve material strength and durability. It would therefore have been obvious to one of ordinary skill in the art to have used higher order isocyanates.
Claims 12-15 are rejected under 35 U.S.C. 103 as being unpatentable over Rosenberg (US 20030065124) as evidenced by Rosenberg (US 5,703,193) as applied to claims 1-11 above, and further in view of Kislig (US 20150353797).
Regarding Claims 12-15,
Rosenberg teaches that water may be used as a chain extender (Paragraph 67). While Rosenberg does not explicitly state that the composition is moisture curable, the curing process in chemical terms means that the available isocyanate functionality of the polyurethane polymer is reacted and can no longer engage in any further chemical reaction. As such, chain extenders function not only to lengthen the polymer chain, but also to render the isocyanate functionality unreactive, thus curing the composition. Therefore, disclosing water as a chain extender would, by necessity, mean that the composition is curable when exposed to moisture. One of ordinary skill in the art, seeking to avoid adding additional components to the composition for ease of manufacture and lowering cost, would look to use moisture to cure the composition. It would therefore have been obvious to have made the composition as disclosed by Rosenberg a moisture curing polyurethane composition.
While Rosenberg teaches a moisture curable polyurethane composition, Rosenberg does not teach the use of the composition on plastic substrates. Kislig teaches a one-component moisture curable polyurethane that is useful as a waterproofing membrane (Abstract) that can be coated onto a variety of substrates, including plastics such as ABS, PVC, EPM, EPDM, PMMA, SAN, and others (Paragraph 146). One of ordinary skill in the art, seeking to expand the use cases for a polyurethane composition, would test the material for compatibility with a variety of substrates. Additionally, the compositions of Rosenberg and Kislig both utilize propylene diol-based polyols and MDI as a diisocyanate. It would therefore have been obvious prior to the effective filing date of the instant application to have used the composition of Rosenberg as a moisture curable polyurethane for application to plastic substrates with a reasonable expectation of success.
Response to Arguments
Applicant's arguments filed 11/19/2025 have been fully considered but they are not persuasive for the following reasons.
On pages 5 and 6, the applicant argues that Rosenberg requires the use of solvent in order to remove the MDI, thus differentiating the instant application from the prior art. The examiner notes that claim 1 is constructed as a product-by-process claim, since the language of the claim is directed towards a linear polymer and then placing limitations upon the manufacture of the polymer. As a product-by-process claim, the patentability is determined solely on the basis of the product (See MPEP 2113.I). The applicant must show that the difference in manufacturing method results in a nonobvious difference in the final product (See MPEP 2113.II). Further, Rosenberg discloses in a comparative example (Comparative Example B ‘124 and Comparative Example C in ‘193) that multiple distillations may be used without solvent in order to remove MDI from the prepolymer. In this example, the amount of free MDI in the prepolymer is reduced below the 0.5 weight percent requirement of claim 1 and because the amount is reduced with each subsequent distillation, the ordinarily skilled artisan would recognize that even in the event that the presence of solvent taught by the exemplary examples of Rosenberg would generate a difference in the prepolymer, Rosenberg teaches that distillation without solvent can be conducted and that multiple distillations can be used to reduce the amount of free isocyanate in the composition. As the amount of free isocyanate decreases with each distillation (57% initially, and 21%, 3%, and 0.7% after the first, second, and third distillations respectively), it would have been obvious that additional distillations would further decrease this value and arrive at the invention disclosed in the instant application.
Also on page 5, the applicant argues that Rosenberg does not explicitly teach the hydroxyl number of the polyol. The examiner agrees that Rosenberg does not mention this number explicitly. However, this number is correlated to the number of hydroxyl groups present in the polyol and the molecular weight of the polyol through a standard equation. Rosenberg teaches a preference for polyols with average hydroxyl functionality of 2 to 2.5 (Column 5, Lines 7-9) and that molecular weights of polyol up to 10,000 may be used (Column 4, Lines 62-64). Based upon these parameters, Rosenberg discloses the use of polyols that would meet the hydroxyl number requirement.
On page 6, the applicant states that there would not have been motivation to combine the teachings of Rosenberg with the teachings of Kislig to generate the prepolymer. The rejection has been modified to render this argument moot.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765