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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 October 7, 2025 has been entered.
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. 102(a)(1) 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 removed “m-xylylene diisocyanate” from the group of iso(thio)cyanate moieties recited in claim 1. Therefore, the rejection has been withdrawn.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”).
Applicant’s arguments and amendments are considered fully responded to within the rejections 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, 4-6, 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”).
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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647
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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.
As to Claim 4: Hori and Giminez the urethane allyl compound of claim 1 (supra).
Hori as modified by Giminez meets the structural limitations of the claimed formula (X1) (see rejection of claim 1 above). It is noted that claim 4 and claim 1, from which claim 4 depends, do not select or require a formula (Y1) or compound (A). Accordingly, the structure (above) reads on the alternative formula (X1) recited in claim 1.
As to Claim 5: Hori and Giminez the urethane allyl compound of claim 1 (supra).
Hori further teaches that the polymerizable compound having a hydroxyl group may be ethylene glycol monoallyl ether ([0076]), which reads on the claimed compound (B-1).
As to Claim 6: Hori and Giminez the urethane allyl compound of claim 3 (supra).
Hori also teaches the reaction of an isocyanate and a polymerizable compound having a hydroxyl group may comprise a methacrylate having a hydroxyl group such as 2-hydroxyethyl (meth)acrylate ([0059]).
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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88
647
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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.
Forming the exemplary allyl alcohol of Hori with the 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 414 g/mol:
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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