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 .
DETAILED ACTION
This Office action is responsive to Applicant's Remarks and Amendment after Non-Final Rejection, filed June 22, 2026. As filed, Claims 1-16 are pending are pending of which claims 1-13 are amended. Claims 14-16 are newly added.
Response to Remarks
Applicant’s amendments have been fully considered and are entered. The status for each rejection and/or objection in the previous Office Action is set out below.
1.The rejection of claims 10-20 under 35 U.S.C. § 112 second paragraph is withdrawn in view of claim amendments to remove parenthesis.
2.The rejection of claims 1-13 under 35 U.S.C. § 103 over JP2019014667, 2019, by Nomura is maintained. Applicant's arguments filed 6/22/2026 have been fully considered but they are not persuasive.
Applicant’s argument that” silica glass used in Example 2 of Nomura '667 does
not satisfy the claim limitation requiring that the specific surface area of the oxide before the heat treatment is at least 1.0 m2/g”(Remarks page 7) and further that “the silica glass used in Example 2 of Nomura '667 publication has a diameter of 150
μm and a density of 1.28 g/cm3, the specific surface area of the silica glass is calculated to be 0.03125 m2/g. Thus, the silica glass used in Example 2 of Nomura '667 does not satisfy the specific feature” of instant claims (Remarks page 8) has been carefully considered, and was not found persuasive.
Per MPEP 716.02 guidance:” Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).”
In the instant case, the prior art by ‘667 publication teaches a method for producing fluorovinyl ether compound as claimed by the same steps which entails reacting acyl fluoro substrate mediated by silicate glass containing sodium oxide- same oxide containing at least an alkaline metal as claimed, and teaches that the oxide which undergoes heat treatment and that the center particle size 150 μm, specific gravity 1.28 g / mL.
Regarding the specific surface area of the oxide before the heat treatment is at least 1.0 m2/g or 1-700m2/g of instant claims, it is noted that 1) the chemical structure of claimed oxide is not recited by instant claims; 2) the prior art specifically teaches that the oxide undergoes heat treatment optimize the particle size of the catalyst and correlation with catalytic activity.
MPEP § 2144.05 II (A) states: “‘[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.’ In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).” Therefore, it would be a matter of routine experimentation for one with ordinary skill in the art to vary the size of oxide for obtaining sizes optimal for catalytic activity, because doing so would be no more than combining known prior art elements and methods to achieve predictable results, namely an optimal size of oxide particles to be subject to heat for obtaining optimal size particle.
The Applicant has not shown evidence of substantially improved and unexpected results or properties between the instantly claimed method for producing fluorovinyl ether compound by the same steps: reacting acyl fluoro substrate mediated oxide- containing at least an alkaline metal as claimed, and oxide which undergoes heat treatment for particle size adjustment. The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages.
As stated in MPEP 716.02 (d) regarding unexpected results commensurate in scope with claimed invention “To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960).”
In reviewing the instant disclosure, the preparative example 1-1 to 6-6 on [0215] -[0290] in which glass beads 1 with specific surface area: 0.5 m2/g, crystallinity: none, aluminosilicate containing sodium); 4.1 m2/g, crystallinity; Na2SiO3
“(specific surface area: 2.5 m2/g, crystallinity: yes)”; alumina
adsorbent 2 containing Na (selexsorb COS manufactured by
BASF, specific surface area: 150 m2/g, crystallinity: yes); Zeolum A-3, Type 585, 20-32 mesh" manufactured by TOSOH CORPORATION, specific surface area: 28 m2/g,
crystallinity: yes, aluminosilicate containing potassium), glass beads
6 (specific surface area: 12.3 m2/g, crystallinity: none etc.
There are no examples or data of the instant disclosure outside of claimed range of specific surface area of oxide before treatment of at least 1 m2/g to 700 m2/g, showing criticality of instantly claimed surface area size.
The Applicant has not shown evidence of substantially improved and unexpected results or properties between the instantly claimed process for producing fluorovinyl ether compound by the same steps and the prior art process for producing the same compound from same starting materials and reagents by same steps.
Please note that if Applicant intends to rely on unexpected or unforeseen results, attention is invited to MPEP 716.02. Absent clear, convincing, side-by-side data demonstrating unobviousness vis-a-vis the prior art commensurate with the scope of protection sought and showing that the claimed process and process disclosed by prior art are distinct, the claims are considered prima facie obvious.
This rejection is still deemed proper, and is therefore maintained.
3.The objection to claims has been addressed by claim amendments. .
The following are maintained/modified of rejections to address newly added claims 14-16 necessitated by Applicants’ amendment, filed on 6/22/2026.
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 1-16 are rejected under 35 U.S.C. 103 as being unpatentable over JP2019014667, 2019, by Nomura (“the ‘667 publication”; cited by Applicants in IDS; translation provided in the PTO-892 mailed 3/25/2026).
Instant claims are drawn to method for producing a fluorovinyl ether compound, which comprises heat-treating a compound having a group represented by formula (1) in the presence of an oxide containing at !east one element selected from the group consisting of alkali metal elements and alkaline earth metal elements, to obtain a fluorovinyl ether compound having a group represented by formula (2), wherein the specific surface area of the oxide before the heat treatment is at least 1.0 m2/g:
F-C(=O)-CF(X)-(CF2)n-O- Formula (1)
Formula (2) is CF2=CF-O-; in the formula (1 ), n is O or 1, and when n is 0, Xis CF3 and when n is 1, X is F.
The ‘667 publication teaches a method for producing perfluoro (polyoxyalkylene alkyl vinyl ether) and a perfluoro (polyoxyethylene alkyl vinyl ether of formula RF (OQF) nOCF = CF2 – which corresponds to claimed formula (I) in which method substrate of formula RF (OQF) nOCF (CF2X) COF- which corresponds to claimed formula (2) is thermally decomposed in the presence of silicate glass (the claimed oxide) and in a gas phase. The ‘667 publication teaches that silicate glass is silicate glass containing sodium oxide or potassium oxide- which corresponds to the claimed oxide containing at !east one element selected from the group consisting of alkali metal elements and alkaline earth metal elements and (instant claims 1, 2, 4, 5) and another element (instant claim 3) (page 3 of translation).
Regarding claim 8, the ‘667 publication teaches producing perfluoro (polyoxyalkylene alkyl vinyl ether) from a specific compound having a perfluoro (polyoxyalkylene) group and an acid fluoride group (page 2 of translation).
Regarding instant claims 9-12, the ‘’667 publication teaches vinyl ethers of formula RF1 (OCF2CF2) n1OCF = CF2 in which formula, RF is a perfluoroalkyl group having 1 to 4 carbon atoms, QF is a perfluoroalkylene group having 1 to 4 carbon atoms, X is a halogen atom, and n is an integer of 1 to 9, RF1 is -CF3, -CF2CF3 or -CF2CF2CF3, and n1 indicates an integer of 3 to 6. Example 1 of page 7, shows reaction of CF 3 CF 2 (OCF 2 CF 2 ) 3 OCF (CF 3 ) COF (Compound 1 1 ) which corresponds to claimed formula 1A or 1A-1 in which variable Rf is a perfluorinated group substituted by etheric oxygen atom, in an autoclave, CH 3 CH 2 (OCH 2 CH 2 ) 2 OCH 2 CH 2 OH (45 0.000 g) was added and stirred while bubbling with nitrogen gas. Next, the internal temperature of the autoclave was kept at 25 to 31 ° C., and F (CF 2 ) 3 OCF (CF 3 ) CF 2 OCF (CF 3 ) COF (175.17 g) was added dropwise over 40 minutes. The autoclave was stirred at 25 ° C for 24 hours while bubbling with nitrogen gas, and CH 3 CH 2 (OCH 2 CH 2 ) 2 OCH 2 CH 2 OC (O) CF (CF 3 ) OCF 2 CF (CF 3 ) O reaction solution (210.03 g) containing (CF 2 ) 3 F was obtained which corresponds to claimed formula 2A or 2A-1 in which variable Rf is a perfluorinated group substituted by etheric oxygen atom.
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Example 2 shows preparation of fluorovinyl ether CF 3 CF 2 (OCF 2 CF 2 ) 3 OCF═CF 2 (Compound 2 1 ) in a fluidized bed tubular reactor filled with glass beads (silicate glass containing sodium oxide, center particle size 150 μm, specific gravity 1.28 g / mL), It was immersed in a salt bath at 325 ° C. nitrogen gas (24.61 L / h) was introduced into the tubular reactor, to initiate a thermal decomposition reaction. After 1 hour, a liquid (13.09 g) distilled in a liquid nitrogen trap was recovered to give f Compound 2 1 95.4% yield. By-product of hydrogen fluoride adduct (page 8 of translation).
Regarding instant claim 13, the ‘667 publication teaches the thermal decomposition reaction, as a continuous reaction using a fluidized bed for production efficiency. The continuous reaction, the compound 1 is vaporized, and then the vaporized compound 1 is passed through a fluidized bed filled with silicate glass heated to the reaction temperature to obtain a gas containing the product ( page 5 of translation).
The differences between the prior art and the claims at issue is that the prior art by the ‘667 publication does not teach specific surface area of the oxide before the heat treatment is at least 1.0 m2/g or 1-700m2/g as recited by instant claims.
However, the ‘667 publication teaches a method to produce the fluorovinyl ether compound as claimed by the same steps which entails reacting acyl fluoro substrate mediated by silicate glass containing sodium oxide- same oxide containing at least an alkaline metal as claimed, and teaches that the oxide which undergoes heat treatment and that the center particle size 150 μm, specific gravity 1.28 g / mL ( example 2 page 8).
The office does not have the facilities and resources to provide the factual evidence needed in order to establish that the silicate glass containing sodium oxide of the prior art does not possess the same material, structural and functional characteristics – specific surface area of the oxide before the heat treatment of at least 1.0 m2/g – as the claimed oxide comprising the same structural elements. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed oxide is of different specific surface area from the silicate glass containing sodium oxide of the prior art taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to produce the fluorovinyl ether compound as claimed by the method taught by the ‘667 publication, because the prior art teaches preparing such compound by the same steps and utilizing same catalyst - silicate glass containing sodium oxide.
In conclusion, the prior art as a whole as taught by the ‘667 publication teaches the reaction of acyl fluorinated substrate to afford the corresponding fluorovinyl ether product in the presence of an oxide containing alkaline metal disclosed by the ‘667 publication; therefore, the prior art teaches the elements of the claimed method producing fluorovinyl ether with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill.
"Exemplary rationales that may support a conclusion of obviousness include: (A) Combining prior art elements according to known methods to yield predictable results ". See MPEP § 2143 .
Consequently, absent a showing of unexpected results, the instant claims are obvious over the prior art.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
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.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
The examiner can normally be reached Monday - Friday (9:00AM - 5:30PM).
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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