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 .
Response to Amendments and Arguments
Applicant’s amendments and arguments, filed October 7, 2025, with respect to the rejection(s) under 35 U.S.C. 103 have been fully considered and are persuasive. Applicant has amended the claims to change the scope of the claims outside the scope of the previous prior art. Specifically, Applicant has amended claim 1 to require wherein the alcohol compound (B) is at least one selected from the group consisting of compounds (B-2) or (B-3). Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Hori et al. (cited in the previous Office Action) in view of Ramon-Giminez et al. (US20170174819, hereinafter referred to as “Ramon”) and Panther (US20110262755, hereinafter referred to as “Panther”).
Applicant’s arguments and amendments have been considered and are fully addressed in the new grounds of rejection below.
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 1 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Hori et al. (JP2007277309, English translation provided for citations, hereinafter referred to as “Hori”) in view of Ramon-Giminez et al. (US20170174819, hereinafter referred to as “Ramon”) and further in view of Panther (US20110262755, hereinafter referred to as “Panther”).
As to Claim 1: Hori teaches an exemplary urethane allyl compound having a urethane bond and an allyloxy group ([0076]-[0077]):
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which is derived from a polymerizable compound having a hydroxyl group which may be ethylene glycol monoallyl ether (i.e., an allyloxy group) and a diisocyanate which is hexamethylene diisocyanate ([0055] and [0076]).
Hori contemplates a variety of exemplary diisocyanate compounds “and the like” capable of undergoing reaction with allyl-bound alcohols to afford the urethane allyl compound having a urethane bond and an allyloxy group, but does not explicitly teach wherein said diisocyanate is a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate or a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane.
Giminez teaches a related acrylate-terminated urethane compound based on the reaction product of at least one diisocyanate and at least one olefinic compound having at least one (meth)acrylate group or vinyl group and one -OH group ([0030]-[0033]). Giminez further teaches that the at least one diisocyanate may be chosen from, inter alia, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and mixtures thereof ([0039]). Giminez also teaches that the diisocyanate may be a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane ([0040]). Hori and Giminez are considered analogous art because they are directed towards the same field of endeavor, namely, urethane/olefin adducts having unsaturated bonds suitable for addition polymerization. It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to substitute the isocyanate component of the urethane allyl compound of Hori with either a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate or a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane based on the finding that Giminez teaches that these compounds are known alternatives to diisocyanate compounds taught by Hori (e.g., hexamethylene diisocyanate) and are suitable for the same purpose of undergoing reaction with -OH moieties on olefin-containing reactants to form olefin-urethane adducts (e.g., urethane acrylates). Substituting equivalents known for the same purpose is prima facie obvious, see MPEP 2144.06 II.
Hori teaches wherein the urethane allyl compound having a urethane bond and an allyloxy may be derived from an allyloxy compound that is ethylene glycol monoallyl ether, but is silent towards wherein the polymerizable compound having a hydroxyl group which may be an allyloxy compound has the structure of the claimed (B-2) or (B-3).
Panther teaches a urethane resin based on the reaction product of an isocyanate component having two or more isocyanate groups and ethylenically unsaturated components that may be allyl components having at least one functional group that is reactive with an isocyanate group and at least one allyl group (Abstract). Panther further teaches wherein said allyl component may have the structure ethylene glycol monoallyl ether or trimethylol propane diallyl ether, shown respectively below ([0059]-[0062]):
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Hori and Panther are considered analogous art because they are directed towards the same field of endeavor, namely, polymerizable urethane allyl compounds. It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to alternatively select trimethylol propane diallyl ether as the allyloxy compound of Hori (i.e., ethylene glycol monoallyl ether) based on the teaching of Panther than both structures are recognized as suitable reaction components for the intended purpose of installing ethylenic unsaturation to urethane/isocyanate compounds such that the compound may be cured.
As to Claim 8: Hori and Giminez the urethane allyl compound of claim 1 (supra).
Hori teaches an exemplary urethane allyl compound having a urethane bond and an allyloxy group ([0076]-[0077]):
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which is derived from a polymerizable compound having a hydroxyl group which may be ethylene glycol monoallyl ether (i.e., an allyloxy group) and a diisocyanate which is hexamethylene diisocyanate ([0055] and [0076]).
Hori contemplates a variety of exemplary diisocyanate compounds “and the like” capable of undergoing reaction with allyl-bound alcohols to afford the urethane allyl compound having a urethane bond and an allyloxy group, but does not explicitly teach wherein said diisocyanate is a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate or a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane.
Giminez teaches a related acrylate-terminated urethane compound based on the reaction product of at least one diisocyanate and at least one olefinic compound having at least one (meth)acrylate group or vinyl group and one -OH group ([0030]-[0033]). Giminez further teaches that the at least one diisocyanate may be chosen from, inter alia, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and mixtures thereof ([0039]). Giminez also teaches that the diisocyanate may be a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane ([0040]). Hori and Giminez are considered analogous art because they are directed towards the same field of endeavor, namely, urethane/olefin adducts having unsaturated bonds suitable for addition polymerization. It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to substitute the isocyanate component of the urethane allyl compound of Hori with either a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate or a mixture of 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)bicyclo[2.2.1]heptane based on the finding that Giminez teaches that these compounds are known alternatives to diisocyanate compounds taught by Hori (e.g., hexamethylene diisocyanate) and are suitable for the same purpose of undergoing reaction with -OH moieties on olefin-containing reactants to form olefin-urethane adducts (e.g., urethane acrylates). Substituting equivalents known for the same purpose is prima facie obvious, see MPEP 2144.06 II.
From the reaction framework taught by Hori with the alternative allyl alcohol of Panther and alternative diisocyanate taught by Giminez, such as a mixture of 2,2,4-trimethylhexamethylene diisocyanate and 2,4,4-trimethylhexamethylene diisocyanate would result in the formula below (and its structural isomer) which has a molecular weight of about 638 g/mol:
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Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Panther (US20110262755, hereinafter referred to as “Panther”).
As to Claim 15: Panther teaches a urethane resin based on the reaction product of an isocyanate component having two or more isocyanate groups and ethylenically unsaturated components comprising (i) an acrylate component having at least one functional group that is reactive with an isocyanate group and at least one acrylate group; and (ii) an allyl components having at least one functional group that is reactive with an isocyanate group and at least one allyl group (Abstract). Panther teaches that the isocyanate compound may be, inter alia, hexamethylene diisocyanate ([0033]). Panther further teaches wherein said acrylate component may have the general formula ([0048]):
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Panther further teaches wherein said allyl component may have the structure ethylene glycol monoallyl ether or trimethylol propane diallyl ether, shown respectively below ([0059]-[0062]):
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The reaction product of the structures above disclosed by Panther read on the claimed formula (Y1).
Conclusion
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.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CULLEN L. G. DAVIDSON IV whose telephone number is (703)756-1073. The examiner can normally be reached M-F 9:30-6:00.
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/C.L.G.D./ Examiner, Art Unit 1767
/MARK EASHOO/Supervisory Patent Examiner, Art Unit 1767
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