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 .
Status of the Claims
The preliminary amendment filed on 07/24/2023 has been entered. Claims 1-6 have been amended and claims 7-10 have been newly added. Thus claims 1-10 are currently pending and are under examination.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2010/0249465A1 (US’465; cited in IDS 07/24/2023).
Regarding claims 1-2 and 6, US’465 teaches a method for producing high-purity vinyl ether which comprises:
a first step; a vinyl ether synthesis step of subjecting an alcohol (I) represented by the general formula (1)
R—O—H (1)
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group), to a vinyl ether formation reaction in the presence of a catalyst to synthesize a vinyl ether (II) represented by the general formula (2)
R—O—CH═CH2 (2)
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group),
wherein the vinyl ether formation reaction is an addition reaction of an alcohol to acetylene;
a second step; a catalyst removal step of removing the catalyst from the reaction mixture obtained in the first step to obtain a crude vinyl ether containing the vinyl ether (II) and the unreacted raw material alcohol (I);
a third step; an acetal formation step of reacting the unreacted raw material alcohol (I) in the crude vinyl ether, with the vinyl ether (II) in the presence of an acid catalyst, to convert the alcohol (I) and vinyl ether (II) into an acetal (III) represented by the general formula (3)
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(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group); and
a fourth step; a distillation and purification step of subjecting a crude vinyl ether containing the acetal (III) to distillation to obtain a high-purity vinyl ether ([0014]-[0020] and [0023]).
As specific examples of the aliphatic hydrocarbon group, there can be mentioned straight chain or branched chain alkyl groups such as ethyl group, n-propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, 2-ethylhexyl group and the like; alkyl groups having cycloalkyl substituent, such as cyclohexylmethyl group, tricyclodecanylmethyl group, 1-adamantylmethyl group and the like; and straight chain or branched chain alkenyl groups such as allyl group, isopropenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, and octenyl group ([0036]).
Regarding claims 2-3, the reference further teaches neutralizing the acid catalyst by the addition of a basic compound ([0075]).
Regarding claim 4, US’465 teaches the first step is conducted in the presence of an alkali metal alcoholate catalyst ([0057]-[0058]).
Regarding claim 5, the distillation of the fourth step is conducted at a pressure of 0.1 to 13.3 kPa ([0080]). The claimed pressure range of 40 kPaA to atmospheric pressure (101.32 kPa) is merely close to that of US’465. According to MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close absent any showing of unexpected results or criticality. In this instance, the current specification describes that the process produces a high-purity IBVE having a purity of 99 mass% or more (pg. 22). Similarly, US’465 teaches a high-purity vinyl ether of 99 mass % or higher in purity can be obtained efficiently ([0079]). As such, due to the absence of evidence indicating that conducting the distillation step at a pressure of 40 kPaA to atmospheric pressure is critical over that of the prior art, the difference in pressure does not support the patentability of subject matter encompassed by the prior art.
Regarding claim 7, the reaction of the first step is conducted in the presence of an organic solvent such as amide solvents, sulfur-containing solvents and glycol dialkyl ether solvents ([0059]).
Regarding claims 8-9, the reaction of the first step in US’465 is conducted at a reaction temperature is ordinarily 80 to 200° C and at a reaction pressure of 0.3 MPa or lower ([0060]).
Regarding claim 10, US’465 teaches that the acid catalyst is selected from inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid, phosphoric acid and the like; organic acids such as carboxylic acid, organic sulfonic acid and the like; and solid acid catalysts such as acidic zeolite, heteropoly-acid, and strongly acidic ion exchange resin ([0067]).
Regarding claims 1-2 and 6, the difference between US’465 and the instant claim is that the instant claim is drawn to a method for producing isobutyl vinyl ether using isobutyl alcohol whereas US’465 teaches a method for producing vinyl ether using alcohol comprising an aliphatic hydrocarbon group selected from a number of straight chain or branched chain alkyl groups, including the instantly claimed isobutyl alcohol group.
Therefore, a skilled artisan would have had reason to try the alcohol of US’465 with the limited number of aliphatic hydrocarbon groups, including the isobutyl group as instantly claimed, with a reasonable expectation of success in obtaining vinyl ether that also includes isobutyl vinyl ether.
MPEP § 2143 states that the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp and that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at 421, 82 USPQ2d at 1397. Therefore, choosing from a finite number of identified, predictable solutions, is likely to be obvious when it does no more than predictable results and with a reasonable expectation of success.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for producing isobutyl vinyl ether as instantly claimed because US’465 teaches a method for producing a number of vinyl ether that also includes isobutyl vinyl ether.
Conclusion
Claims 1-10 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692