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 .
Applicant's election with traverse of Group I and (A1) + ((B1) as species in the reply filed on 6/3/26 is acknowledged. The traversal is on the ground(s) that the previous action provided no examples or explanation why the two groups and various species are mutually exclusive – simply stating a conclusion. This is not found persuasive because the restriction requirement certainly did provide such an explanation. To reiterate:
The reactions of (I) and (II) each use different starting materials. Group I is the reaction of fluorinated compounds having a second reactive halogen with either boronic compounds or zinc compounds. On the other hand, Group II starts with a zinc containing fluoro-compound and reacts with a reactive halogen compound. A search for the claimed reaction scheme would require a search for the starting materials. A search for fluorinated compounds having a second reactive halogen is a different search than a search for zinc containing fluoro-compounds. A search for boronic and zinc compounds is different from a search for halogen compounds.
The species are independent or distinct because fluorinated compounds having one or two further reactive halogens is a different compound from a fluorinated compound having a zinc group. Zinc compounds B1 are different from boronic compounds B2 which are different from halogen compounds B3. In addition, these species are not obvious variants of each other based on the current record.
The requirement is still deemed proper and is therefore made FINAL.
Claims 2,4,6,8,10,12 and 14-16 withdrawn from further consideration pursuant to 37 CFR 1.142(b).
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 3 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
The claim’s (CR7R8-R9R10) is chemically impossible as the carbon has only four available bonding sites. This structure could not bond to the remainder of the compound.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1,7,9,11 and 13 rejected under 35 U.S.C. 102(a)(1) as being anticipated by JP2006316113.
The reference exemplifies (#1 paragraph 226) reacting octafluoropentyl iodide with allylzinc bromide in the presence of a Pd catalyst. This can be depicted as:
HCF2CF2CF2CF2CH2-I + BrZnCH2CH=CH2
↓
HCF2CF2CF2CF2CH2-CH2CH=CH2
The iodide reactant qualifies as applicant’s (A1) with G1 being a fluoroalkyl; L1 being a bond and R1=R2= hydrogen.
The allylzinc bromide qualifies as applicant’s (B1) with R11 being -CH2CH=CH2 and R12 being Br.
The final structure qualifies as applicant’s (C1).
In regards as applicant’s dependent claims:
The -CH2CH=CH2 qualifies as applicant’s R11 of applicant’s claim 7 with R21 and R23 being a bond; R22 being hydrogen and “a” being one.
X1 is iodide in the cited example – meeting applicant’s claim 9.
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.
Claim 5 rejected under 35 U.S.C. 103 as being unpatentable over JP2006316113.
JP2006316113 applies as explained above.
The cited example’s HCF2CF2CF2CF2CH2-I has -CH2- in applicant’s -L1-CR1R2- position.
However, the reference (paragraph 196) more generally teaches the iodide starting compound may be F(CF2)3-10CH2CH2-I which has a -CH2CH2- in applicant’s -L1-CR1R2- position.
The structure resulting from substituting F(CF2)3-10CH2CH2-I in place of the iodide compound in the cited example would have been obvious structure from the reference’s clear teachings.
Claims 1,5,7,9,11 and 13 rejected under 35 U.S.C. 103 as being unpatentable over Sakoh 2015/0148509 in view of Chapter 9.28 of Comprehensive Inorganic Chemistry II in further view of JP2006316113.
Sakoh exemplifies (#1) reacting a fluorinated polyether iodide with allyltributyltin. This can be depicted as: C F3O-(CF2O)p-(C2 F4O)q - CF2CH2-I + (CH3CH2CH2CH2)3SnCH2CH=CH2
↓
C F3O-(CF2O)p-(C2 F4O)q - CF2CH2-CH2CH=CH2
The iodide reactant qualifies as applicant’s (A1) with G1 being a polyoxyfluoroalkylene; L1 being a bond and R1=R2= hydrogen.
The final structure qualifies as applicant’s (C1) with R11 being -CH2CH=CH2.
Despite the allyltributyltin supplying the -CH2CH=CH2 to make the identical final product as applicant’s final product, allyltributyltin does not qualify as applicant’s (B1).
Sakoh’s reaction is known as a “Stille coupling reaction” (see page 780-783 of the Comprehensive Inorganic Chemistry text).
The “Negishi coupling reaction” (see page 783-785) is a known alternative to the “Stille coupling reaction”. Instead of the R2-Sn(R)3 reacting with the organic halide R1-X, to form R1-R2, the Negishi reaction employs R2-Zn-Y which also results in the R1-R2 compound.
The Negishi reaction use of organozincs is said to be more tolerant of functional groups (page 783 right column) and is highly reactive (top page 784).
It would be been obvious to produce Sakoh’s allyl terminated fluorpolyether through a “Negishi” reaction – ie by utilizing an allylzinc halide in place of allyltributyltin as the same final product results and the Negishi and Still reactions are recognized as alternatives to one another. Additionally, the Negishi route has some recognized advantages.
JP2006316113 (example 1) is cited to show allylzinc bromide exists.
In regards as applicant’s dependent claims:
Sakoh’s cited example’s iodide has -CH2- in applicant’s -L1-CR1R2- position.
However, Sakoh (paragraph 22 when “n”=2) more generally teaches the iodide starting compound may have -CH2CH2- in applicant’s -L1-CR1R2- position which meets applicant’s claim 5.
The -CH2CH=CH2 qualifies as applicant’s R11 of applicant’s claim 7 with R21 and R23 being a bond; R22 being hydrogen and “a” being one.
X1 is iodide in Sakoh’s example – meeting applicant’s claim 9.
Comprehensive Inorganic Chemistry II (page 783 left column) recognizes suitable catalysts are Ni or Pd based – meeting applicant’s claims 11 and 13.
Claims 1,5,7,9,11 and 13 rejected under 35 U.S.C. 103 as being unpatentable over Valsecchi 2021/0317305 in view of JP2006316113.
Valsecchi exemplifies (paragraph 128-130) reacting a fluorinated polyether bromide with allylmagnesium bromide. This can be depicted as: C F3O-(CF2F2O)p-(CF2O)q - CF2CH2-Br + BrMgCH2CH=CH2
↓
C F3O-(CF2F2O)p-(C F2O)q - CF2CH2-CH2CH=CH2
The fluorinated bromide reactant qualifies as applicant’s (A1) with G1 being a polyoxyfluoroalkylene; L1 being a bond and R1=R2= hydrogen.
The final structure qualifies as applicant’s (C1) with R11 being -CH2CH=CH2.
Despite the allylmagnesium bromide supplying the -CH2CH=CH2 to make the identical final product as applicant’s final product, allylmagnesium bromide does not qualify as applicant’s zinc containing (B1).
The reaction of fluorinated organohalides with allylmetallic halides to form unsaturated fluorinated compounds is also taught by JP2006316113. J’113 exemplifies (#1) reacting octafluoropentyl iodide with allylzinc bromide in the presence of a Pd catalyst to form HCF2CF2CF2CF2CH2-CH2CH=CH2. J’113 (paragraph 94) recognizes CH2=CHZnBr and CH2=CHMgBr as equivalents for reactions with fluorinated organohalides to form unsaturated fluorinated compounds.
It would have been obvious to substitute CH2=CHCH2ZnBr for Valsecchi’s CH2=CHCH2MgBr as the two are expected to result in the same final product. Simple substitution of one known element for another to obtain predictable results is a suitable rationale for prima facie obviousness (MPEP 2143 I.).
In regards as applicant’s dependent claims:
Valsecchi’s cited example’s flourinated polyether bromide has -CH2- in applicant’s -L1-CR1R2- position. However, Valsecchi (claim 21 when “n”=2) more generally teaches the bromide starting compound may have -CH2CH2- in applicant’s -L1-CR1R2- position which meets applicant’s claim 5.
The -CH2CH=CH2 qualifies as applicant’s R11 of applicant’s claim 7 with R21 and R23 being a bond; R22 being hydrogen and “a” being one.
X1 is bromine in Valsecchi’s example. However, any halogen (paragraph 55) may be used – suggesting the iodine of applicant’s claim 9.
JP2006316113’s example 1 utilizes a Pd based catalyst – meeting applicant’s claims 11 and 13.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID J BUTTNER whose telephone number is (571)272-1084. The examiner can normally be reached M-F 9-3pm.
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/DAVID J BUTTNER/Primary Examiner, Art Unit 1765 6/23/26
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