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.
Status of Claims
The examiner acknowledges the addition of claim 16. Claims 1-16 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 § 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 and 16 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, 4, and 16,
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. Further, while Rosenberg does not teach a range of between 6 and 10 mg KOH/g as in claim 16, as stated above, Rosenberg only provides a typical range and does not place an explicit ceiling on the molecular weight, and by extension, the hydroxyl number of the polyol in contrast to a specific teaching regarding low molecular weight polyols (those below 400 molecular weight) and when they may be included (Paragraph 58). One of ordinary skill in the art would recognize that the chain length of the polyol will have effects on polymer properties such as flexibility and strength and would be motivated to adjust the chain length in order to meet strength and flexibility requirements in the final composition. As such, it would have been obvious prior to the effective filing date of the instant application to have selected any molecular weight above 400 and thus any hydroxyl value which corresponds to this.
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 5/5/2026 have been fully considered but they are not persuasive for at least the following reasons.
On pages 6 and 7, the applicant states that polymers are not pure substances and that therefore the lack of solvent gives the polymer patentable weight. The examiner disagrees. In this case, the applicant is arguing that conducting a polymerization reaction in a substantially similar manner to that of Rosenberg and differing merely in the lack of solvent used to remove remaining monomeric diisocyanate results in a different polymer. While this may result in a difference in impurities found in the polymer, the polymer itself, which is the invention of the independent claim, is itself not different based upon this alteration of the process. Additionally, the examiner notes that Rosenberg demonstrates that reduction in monomeric diisocyanate can be accomplished without using solvent in comparative example B, which in spite of the applicant’s argument on page 8 that it represents an unpreferred alternative, does not remove the fact that Rosenberg teaches this method is viable, though not as efficient or even preferred. The examiner is bound by the totality of the teachings, and not simply the preferred embodiments. All the disclosures in a reference must be evaluated for what they fairly teach one of ordinary skill in the art even though the art teachings relied upon are phrased in terms of a non-preferred embodiment or even as being unsatisfactory for the intended purpose, In re Boe, 148 USPQ 507 (CCPA 1966); In re Smith, 65 USPQ 167 (CCPA 1945); In re Nehrenberg, 126 USPQ 383 (CCPA 1960); In re Watanabe, 137 USPQ 350 (CCPA 1963). Finally, while the applicant alleges that minor amounts of solvent present in the polymer as an impurity would alter its properties, the burden is on the applicant to demonstrate this through disclosure of data that supports this position. Because the applicant does not present such data, the burden to demonstrate a difference remains with the applicant. "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.I.
On page 7, the applicant states that solvent can migrate out of the composition after curing and that further, the presence of solvent does not allow for the direct reuse of this diisocyanate. In response to the applicant's argument, it is noted that the features upon which applicant relies (i.e., the migration of solvent as well as the reuse of the diisocyanate) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
Finally, on page 9 the applicant states that Rosenberg fails to teach the use of low hydroxyl number polyols. While the examiner agrees that Rosenberg does not explicitly teach such compounds, as noted in the rejection Rosenberg merely points to a typical range of molecular weight for the polyol, and by extension the hydroxyl number and not a direct teaching of a range. Further, Rosenberg does explicitly teach away the use of low molecular weight polyol except in certain circumstances (Paragraph 58). One of ordinary skill in the art would reasonably view this as teaching away from the use of low molecular weight polyol while explicitly not placing an upper bound on the polyol weight since no analogous guidance is provided on the higher molecular weight, and by extension, low hydroxyl number polyol.
In summary, while the applicant argues that the polymer taught by Rosenberg is not the same as that of the instant application, the applicant has not demonstrated this to be the case. Additionally, while the applicant argues that Rosenberg does not teach polyols of the correct hydroxyl number, the examiner disagrees as Rosenberg provides no hard and fast range for the size of this polymer and further, while Rosenberg does explicitly limit low molecular weight, Rosenberg provides no similar limitations on the high end. As a result, the rejection is maintained.
Conclusion
THIS ACTION IS MADE FINAL. 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 ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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, Heidi Kelley can be reached at 571-270-1831. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
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