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 .
This Office action is in response to the amendment filed 9/2/2026. Claims 1-3 and 6-11 are amended; claims 5, 12 and 14-15 are cancelled; and claims 17-18 are withdrawn from consideration as being drawn to non-elected invention. Accordingly, claims 1-4, 6-11, 13 and 16-18 are currently pending in the application.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 1-4, 6-10, 13 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Gallio (JP 2001-517680 A).
It is noted that JP 2001-517680 A is in Japanese. A copy of the machine translation into English is provided with Office action mailed 6/2/2026. All line/paragraph citations in the body of rejection below are to the English translation unless explicitly stated.
Regarding claims 1-3 and 7-8, Gallio discloses a composition for inhibiting radical polymerization of monomers having ethylenically unsaturated bonds, characterized in that it comprises at least one catechol (i.e., reads on polymerization inhibitor in present claim 1) and at least one aromatic ether (overview). The monomer containing unsaturated bond of ethylenic type is a vinyl monomer (paragraph 0052) such as methyl methacrylate (paragraph 0053) which reads on methyl methacrylate in present claim 1. The aromatic ether is represented by formula:
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wherein R5 are methyl, ethyl, n-propyl, isopropyl (i.e., reads on aryl alkyl ether in present claims wherein R6 and R7 = hydrogen), sec-butyl and tert-butyl (paragraphs 0034-0036) which reads on aryl alkyl ether in present claims wherein R6 = hydrogen and R7 = C1-alkyl. Suitable aromatic ethers include anisole and phenetole (paragraph 0038). It is noted that anisole and phenetole are aromatic ethers wherein Y = hydrogen atom, and R5 is methyl (anisole) and ethyl (phenetole).
Gallio are silent with respect to concentration of methyl methcrylate; concentration of polymerization inhibitor (i.e., component B) and aryl alkyl ether (i.e., component A).
However, Gallio teaches that there is no advantage to adding a large amount of polymerization inhibitor. The optimal amount that can be added depends on nature of the monomer to be stabilized containing an unsaturated bond of ethylenic type. Therefore, the ideal amount of inhibitor must be estimated on a case by case basis. Generally the composition is added in amount such that the concentration of catechol derivative is in the range of 10 ppm to 300 ppm (paragraphs 0049-0051). A preferred composition comprises from 30 to 60% by weight of catechol derivative and 40% to 70% by weight of aromatic ether (paragraph 0041). Therefore, it would have been obvious to one skilled in art prior to the filing of present application to include aromatic ether and catechol in equal amounts such as 150 ppm (i.e., 0.015%) and consequently methyl methacrylate in amounts of 99.97% by weight (i.e., reads on the amount of methyl methacrylate in present claim 1), absent evidence to the contrary.
Regarding concentration of polymerization inhibitor (i.e., component B) and aryl alkyl ether (i.e., component A), Gallio teaches that there is no advantage to adding a large amount of polymerization inhibitor. The optimal amount that can be added depends on nature of the monomer to be stabilized containing an unsaturated bond of ethylenic type. Therefore, the ideal amount of inhibitor must be estimated on a case by case basis. Generally the composition is added in amount such that the concnetration of catechol derivative is in the range of 10 ppm to 300 ppm (paragraphs 0049-0051). A preferred composition comprises from 30 to 60% by weight of catechol derivative and 40% to 70% by weight of aromatic ether (paragraph 0041). Therefore, given that composition inhibits polymerization of vinyl monomers such as methyl methacrylate, composition may be added in small amounts and estimated on a case by case basis, it is the Office’s posiiton that it is within the scope of one skilled in art prior to the filing of present application to optimize the amount of aromatic ether to any concentration (such as 10 to 5,000 μmol/L as in present claim 1; 50 to 3,000 μmol/L as in present claim 2; and 50 to 1,000 μmol/L as in present claim 3); and catechol (i.e., a polymerization inhibitor) to any concentration (such as 10 to 5,000 μmol/L as in present claim 1; 40 to 3,000 μmol/L as in present claim 2; 40 to 1,000 μmol/L as in present claim 3; 40 to 3,000 μmol/L as in present claim 7; and 40 to 1,000 μmol/L as in present claim 8), absent evidence to the contrary.
Regarding claim 4, it is noted that when R5 = isopropyl, the aromatic ether has a molecular weight of 120 g/mol.
Regarding claim 6, Gallio teaches that there is no advantage to adding a large amount of polymerization inhobitor. The optimal amount that can be added depends on the nature of the monomer to be stabilized containing an unsaturated bond of ethylenic type. Therefore, the ideal amount of inhibitor must be estimated on a case by case basis. Generally the composition is added in an amount such that the concentration of catechol derivative is in the range of 10 ppm to 300 ppm (paragraphs 0049-0051). A preferred composition comprises from 30 to 60% by weight of catechol derivative and 40% to 70% by weight of aromatic ether (paragraph 0041) which overlaps with the ratio in present claim 6.
Regarding claims 9-10, Gallio teach that composition comprises catechol (overview) which reads on the polymerization inhibitor is a phenol compound in present claims 9 and 10.
Regarding claim 13, it is noted that the composition does not include diacetyl (i.e., reads on conentration of 55 μmol/L or less which incldues zero).
Regarding claim 16, it is noted that when R5 = isopropyl, the aromatic ether of formula:
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reads on component A of formula I in present claim 16 wherein R1 to R7 = hydrogen atom.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Gallio (JP 2001-517680 A) in view of Martan et al (US 2004/0236143 A1).
The discussion with respect to Gallio in paragraph 8 above is incorporated herein by reference.
Gallio is silent with respect to species of inhibitor.
However, Martan in the same field of endeavor teach a method for producing methacrylic acid ester in the presence of at least one polymerization inhibitor (abstract). Examples of inhibitors include 6-tert-butyl-2,4-dimethylphenol, 2,6-di-tert-butyl-4-methyl phenol, N,N-diphenylamine, and triphenyl phosphite (paragraph 0088). Case law holds that selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). Therefore, in light of the teachings in Martan et al and case law, it would have been obvious to one skilled in art prior to the filing of present application to include the polymerization inhibitor, of Martan et al, in the methyl methacrylate composition of Gallio, absent evidence to the contrary.
Response to Arguments
The rejections under 35 U.S.C. 103 as set forth in paragraphs 17-19, of Office action mailed 6/2/2206, are withdrawn in view of amendments and/or applicant arguments and/or new grounds of rejection set forth in this Office action, necessitated by amendment.
While the grounds of rejection are changed, it was still deemed appropriate to address some of the arguments which would be pertinent to new grounds of rejection in this office action (See paragraph 11 below).
Applicant's arguments filed 9/2/2206 have been fully considered but they are not persuasive. Specifically, general thrust of applicant argument is that Gallio does not disclose a composition containing 99.8 to 99.99% by mass methyl methacrylate, component A having the specifically recited substituents R¹- R⁷, and polymerization inhibitor component B, wherein both MA and MB are each 10 to 5,000 µmol/L, for suppressing generation of methyl methacrylate dimers and methyl pyruvate during storage. Although Gallio teaches that the amount of its polymerization-inhibiting composition may be selected depending upon the monomer to be stabilized, those general teachings do not disclose or suggest the particular combination of concentration ranges and high methyl methacrylate concentration to suppress formation of methyl methacrylate dimers and methyl pyruvate.
In response, present claims require a composition comprising methyl methacrylate, polymerization inhibitor and aryl alkyl ether compound in specific amounts. Gallio teaches a composition for inhibiting radical polymerization of monomers having ethylenically unsaturated bonds including methyl methacrylate. The composition includes both a polymerization inhibitor such as catechol and an aryl alkyl ether. The composition is added such that catechol derivative is present in amounts of 10 to 300 ppm. A preferred composition comprises 30 to 60% by weight of catechol derivative and 40 to 70% by weight of aromatic ether. The ideal amount of inhibitor must be estimated on a case-by-case basis. Therefore, it is the Office’s position that concentrations of each of these components is optimizable by one of ordinary skill in art prior to the filing of present claims.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KARUNA P REDDY whose telephone number is (571)272-6566. The examiner can normally be reached 8:30 AM to 5:00 PM M-F.
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, Arrie (Lanee) Reuther can be reached at 571-270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KARUNA P REDDY/Primary Examiner, Art Unit 1764
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