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 .
Claim Objections
Claim 1 and the claims dependent therefrom are objected to because Applicant mislabels reactant (A) as an alkenyl ether whereas the Examiner submits that it is instead an alkenyl ester.
The article “a” following the word “provide” in the thrd-to-last line of claim 1 should be deleted.
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.
Claims are rejected under 35 U.S.C. 103 as being unpatentable over Noda et al., JP 09-316085 in view of Kimae et al., U.S. Patent # 5,750.753.
Applicant is referred to Example 1 where allyl methacrylate is reacted with 1,1,1,3,5,5,5-heptamethyltrisiloxane in the presence of chloroplatinic acid wherein the calculated ratio of organohydrogensiloxane to allyl methacrylate is 0.78:1. There is admittedly no mention of using a phosphine promoter of the structure delineated at the end of claim 1.
Kimae et al. observes that the hydrosilylation of allyl (meth)acrylate does not exhibit high chemo/regioselectivity (column 1, lines 29-50). They, therefore, propose the incorporation of an organic phosphorus compound to enhance the regioselectivity of which there are about 15 exemplifications in column 2. Whereas it is appreciated that among the named phosphorus promoters are 1,2-bis(diphenylphosphino)ethane and bis(diphenylphosphino)propane, the structural homologue where the phosphorus atoms are separated by a single methylene group is not expressly named. On the other hand, formula (III) at the top of column 3 embraces bis-phosphine compounds where X is CH2 and m =1 thus it is the Examiner’s assertion that one of ordinary skill would also find the employment of bis(diphenylphosphino)methane (claim 10) to be prima facie obvious. Not only this but, among the triorganophosphines contemplated is tricyclohexylphoshine and the same hydrocarbon substituents mentioned in prior art formula II are also found in formula III hence another embodiment where cyclohexyl groups replace the phenyl groups in bis(diphenylphosphino)methane would also be recognized by a skilled artisan as having utility in augmenting the selectivity of a hydrosilylation reaction involving allyl (meth)acrylate and an organosilicon compound featuring silicon-bound hydrogen atoms.
Applicant is encouraged to review Table 1 of the reference where the results of hydrosilylation reactions of allyl acrylate involving the two aforementioned bisphosphines, embodiments 3 and 4, are compared with that in reference example 1 where chloroplatinic acid was used to the exclusion of a phosphine promoter according to that invention. It will be noted that the selectivity for the desired product is approximately halved. Given the structural similarities of bis(diphenylphosphino)methane to the compounds identified in embodiments 3 and 4, and a skilled artisan’s understanding that the promoters act by coordinating the platinum metal center to create the proper electronic/steric environment for enhanced selectivity, there is certainly a reasonable expectation that it too will substantially improve the selectivity relative to results documented in reference example 1.
As for claim 8, the catalyst and phosphorus compound are combined prior to the introduction of the organohydrogensiloxane in the description under the heading “EMBODIMENT 1”. See also column 5, lines 15-19. The materials are mixed in the presence of toluene thus satisfying claim 9.
Regarding claims 10 and 13, it is reiterated that the skilled artisan recognizes the phosphorus promoter as being a compound that ligates the platinum metal center and so a mol ratio of 1:1 in each of these would be obvious. (The Examiner appreciates that two equivalents of a phosphine compound are often observed in the preparation of platinum compounds but the bidentate ones occupy more of the coordination sphere and, therefore, it would at least be obvious to try systems involving a single equivalent of bis(diphenylphosphino)methane per mol of platinum.) As an aside, this same amount would be that necessary to realize the same degree of selectivity and conversion as are mandated in claim 1.
As for claim 14, EMBODIMENT 1 discloses the use of BHT as an acrylate polymerization inhibitor. Finally, the isolation of a target product, where feasible as is usually the case with small molecules, is ubiquitously practiced in the prior art and, therefore, claim 15 is likewise unpatentable.
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Noda et al., JP 09-316085 in view of Kimae et al., U.S. Patent # 5,750.753 as applied to claims 1, 3-6, and 8-15 above, and further in view of Karstedt, U.S. Patent # 3,715,334.
Both Noda in Example 1 and Kimae in embodiment 1 utilize chloroplatinic acid (also known as Speier’s catalyst). Karstedt developed as an improvement on Speier’s technology the compound mentioned in claim 7, which was superior for its substantially higher activity, thus enabling the use of considerably less of the platinum compound to facilitate the reaction of ethylenically-unsaurated compounds with SiH-bearing compounds. See the discussion in column 1. Not only this but Karstedt’s catalyst is devoid of chlorine ion content, which can contribute the side-product formation. It is for these reasons that one of ordinary skill would be motivated to replace chloroplatinic acid with the complex cited in claim 7. See also Example 1.
Allowable Subject Matter
Claim 2 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The focus of Noda is entirely on the introduction of (meth)acryl groups and select other functional groups. Allyl acetate is not a reactant of interest nor is it clear why one of ordinary skill would be motivated to use it as a starting material.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MARC S ZIMMER whose telephone number is (571)272-1096. The examiner can normally be reached M-F 8:30-5:00.
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August 17, 2026
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765
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