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 .
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-12, in the reply filed on 05/06/2026 is acknowledged.
Claim 13 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 05/06/2026.
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claims 6 and 11 are objected to because of the following informalities: Claim 6 recites ”reaction solvent replaced by workup solvent” in lines 2-3, which is grammatically incorrect. The Office suggests that Applicant change this to “reaction solvent is replaced by workup solvent”. Claim 11 recites “ .),” in line 7, which includes a period that is before the end of the claim and that is not used with an abbreviation or reference character, which includes a closed parenthesis and a comma that are not needed. The Office suggests that Applicant delete the “ .),”. Appropriate correction is required.
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.
Claims 1-12 are 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.
Claim 1 recites the limitation “A process for modifying an aromatic polyether backbone, in particular for modifying an aromatic moiety of the aromatic polyether backbone” in lines 1-2, which is indefinite because the phrase “in particular” makes it unclear if “for modifying an aromatic moiety of the aromatic polyether backbone” is a required limitation or an optional limitation. For further examination of the claims, this limitation is interpreted as “A process for modifying an aromatic polyether backbone or for modifying an aromatic moiety of the aromatic polyether backbone”.
Claim 7 recites the limitation “
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” in lines 4-7, which is indefinite because the claim does not define “n”. For further examination of the claims, the Office interprets “n is 1 or greater”.
Claim 9 recites the limitation “ethers (dimethyl ether, diethyl ether, di-n-butyl ether, tetrahydrofuran, dioxane, etc.)” in lines 3-4, which is indefinite because it is unclear if “dimethyl ether, diethyl ether, di-n-butyl ether, tetrahydrofuran, dioxane, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “ethers, dimethyl ether, diethyl ether, di-n-butyl ether, tetrahydrofuran, dioxane”.
Claim 9 recites the limitation “esters (ethyl acetate, isopropyl acetate, methyl benzoate, ethyl benzoate, dimethyl succinate, methyl p-toluate, etc.)” in lines 4-5, which is indefinite because it is unclear if “ethyl acetate, isopropyl acetate, methyl benzoate, ethyl benzoate, dimethyl succinate, methyl p-toluate, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “esters, ethyl acetate, isopropyl acetate, methyl benzoate, ethyl benzoate, dimethyl succinate, methyl p-toluate,”.
Claim 9 recites the limitation “alcohols (methanol, ethanol, n-butanol, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoro-2-propanol, etc.)” in lines 5-6, which is indefinite because it is unclear if “methanol, ethanol, n-butanol, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoro-2-propanol, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “alcohols, methanol, ethanol, n-butanol, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoro-2-propanol,”.
Claim 9 recites the limitation “chloroalkanes (dichloromethane, 1,2-dichloroethane, etc.)” in lines 6-7, which is indefinite because it is unclear if “dichloromethane, 1,2-dichloroethane, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “chloroalkanes, dichloromethane, 1,2-dichloroethane,”.
Claim 9 recites the limitation “nitroalkanes (nitromethane, nitroethane, 1-nitropropane, etc.)” in line 7, which is indefinite because it is unclear if “nitromethane, nitroethane, 1-nitropropane, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “nitroalkanes, nitromethane, nitroethane, 1-nitropropane,”.
Claim 9 recites the limitation “haloaromatics (chlorobenzene, chlorotoluene, bromobenzene, fluorobenzene, 1,2-difluorobenene, hexafluorobenzene, alpha,alpha,alpha-trifluorotoluene, etc.)” in lines 8-9, which is indefinite because it is unclear if “chlorobenzene, chlorotoluene, bromobenzene, fluorobenzene, 1,2-difluorobenene, hexafluorobenzene, alpha,alpha,alpha-trifluorotoluene, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “haloaromatics, chlorobenzene, chlorotoluene, bromobenzene, fluorobenzene, 1,2-difluorobenene, hexafluorobenzene, alpha,alpha,alpha-trifluorotoluene,”.
Claim 9 recites the limitation “nitroaromatics (nitrobenzene, nitrotoluene, etc.)” in lines 9-10, which is indefinite because it is unclear if “nitrobenzene, nitrotoluene, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “nitroaromatics, nitrobenzene, nitrotoluene,”.
Claim 9 recites the limitation “nitriles (acetonitrile, propionitrile, isobutyronitrile, benzonitrile, etc.)” in line 10, which is indefinite because it is unclear if “acetonitrile, propionitrile, isobutyronitrile, benzonitrile, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “nitriles, acetonitrile, propionitrile, isobutyronitrile, benzonitrile,”.
Claim 9 recites the limitation “carboxylic acids (acetic acid, propionic acid, pivalic acid, benzoic acid, malonic acid, succinic acid, etc.)” in lines 11-12, which is indefinite because it is unclear if “acetic acid, propionic acid, pivalic acid, benzoic acid, malonic acid, succinic acid, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “carboxylic acids, acetic acid, propionic acid, pivalic acid, benzoic acid, malonic acid, succinic acid,”.
Claim 9 recites the limitation “sulfonic acids (methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, etc.)” in lines 12-13, which is indefinite because it is unclear if “methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “sulfonic acids, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid,”.
Claim 9 recites the limitation “water (monohydrate, dihydrate)” in line 13, which is indefinite because it is unclear if “monohydrate, dihydrate” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. For further examination of the claims, this limitation is interpreted as “water, monohydrate, dihydrate”.
Claim 9 recites the limitation “sulfones (tetramethylene sulfone, dimethyl sulfone, diethyl sulfone, etc.)” in lines 13-14, which is indefinite because it is unclear if “tetramethylene sulfone, dimethyl sulfone, diethyl sulfone, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “sulfones, tetramethylene sulfone, dimethyl sulfone, diethyl sulfone,”.
Claim 9 recites the limitation “sulfoxides (dimethyl sulfoxide, diethyl sulfoxide, etc.)” in lines 14-15, which is indefinite because it is unclear if “dimethyl sulfoxide, diethyl sulfoxide, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “sulfoxides, dimethyl sulfoxide, diethyl sulfoxide,”.
Claim 9 recites the limitation “thioethers (methyl sulfide, ethyl sulfide, propyl sulfide, isopropyl sulfide, tetrahydrothiophene)” in lines 15-16, which is indefinite because it is unclear if “methyl sulfide, ethyl sulfide, propyl sulfide, isopropyl sulfide, tetrahydrothiophene” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “thioethers, methyl sulfide, ethyl sulfide, propyl sulfide, isopropyl sulfide, tetrahydrothiophene”.
Claim 9 recites the limitation “mineral acids (phosphoric acid, sulfuric acid, etc.)” in line 16, which is indefinite because it is unclear if “phosphoric acid, sulfuric acid, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “mineral acids, phosphoric acid, sulfuric acid,”.
Claim 10 recites the limitation "the catalyst quencher" in line 2. There is insufficient antecedent basis for this limitation in the claim because claim 10 depends directly from claim 1, and claim 1 does not recite the limitation “a catalyst quencher”. Since claim 3 is the previous claim that recites the limitation “at least one catalyst quencher” in lines 2-3, for further examination of the claims, it is interpreted that claim 10 depends from claim 3.
Claim 10 recites the limitation “alkyl phosphates (trimethyl phosphate, triethyl phosphate, tributyl phosphate, etc.)” in lines 3-4, which is indefinite because it is unclear if “trimethyl phosphate, triethyl phosphate, tributyl phosphate, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “alkyl phosphates, trimethyl phosphate, triethyl phosphate, tributyl phosphate,”.
Claim 10 recites the limitation “carboxylic acid amides, (dimethyl formamide, dimethyl acetamide, N-methyl pyrrolidone, N-butyl pyrrolidone, etc.)” in lines 4-5, which is indefinite because it is unclear if “dimethyl formamide, dimethyl acetamide, N-methyl pyrrolidone, N-butyl pyrrolidone, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “carboxylic acid amides, dimethyl formamide, dimethyl acetamide, N-methyl pyrrolidone, N-butyl pyrrolidone,”.
Claim 10 recites the limitation “ureas (dimethylethylene urea, tetramethyl urea, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, etc.)” in lines 5-6, which is indefinite because it is unclear if “dimethylethylene urea, tetramethyl urea, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “ureas, dimethylethylene urea, tetramethyl urea, 1,3-dimethyl-2-imidazolidinone, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone,”.
Claim 11 recites the limitation “the scavenger” in line 2. There is insufficient antecedent basis for this limitation in the claim because claim 11 depends directly from claim 1, and claim 1 does not recite the limitation “a scavenger”. Since claim 4 recites the limitation “at least one catalyst scavenger” in line 2, for further examination of the claims, it is interpreted that claim 11 depends from claim 4.
Claim 11 recites the limitation “hydrofluoric acid salts (ammonium fluoride, lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, rubidium fluoride, magnesium fluoride, calcium fluoride, strontium fluoride, barium fluoride, etc.)” in lines 3-5, which is indefinite because it is unclear if “ammonium fluoride, lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, rubidium fluoride, magnesium fluoride, calcium fluoride, strontium fluoride, barium fluoride, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “hydrofluoric acid salts, ammonium fluoride, lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, rubidium fluoride, magnesium fluoride, calcium fluoride, strontium fluoride, barium fluoride,”.
Claim 11 recites the limitation “sulfuric acid salts (sodium sulfate, potassium sulfate, etc.)” in lines 5-6, which is indefinite because it is unclear if “sodium sulfate, potassium sulfate, etc.)” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “sulfuric acid salts, sodium sulfate, potassium sulfate,”.
Claim 11 recites the limitation “phosphoric acid salts (trisodium phosphate, tripotassium phosphate, etc.)” in line 6, which is indefinite because it is unclear if “trisodium phosphate, tripotassium phosphate, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “phosphoric acid salts, trisodium phosphate, tripotassium phosphate,”.
Claim 11 recites the limitation “pyrophosphoric acid salts (sodium pyrophosphate, potassium pyrophosphate, etc.) .)” in lines 6-7, which is indefinite because it is unclear if “sodium pyrophosphate, potassium pyrophosphate, etc.” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. Also, the scope of “etc.” is unclear. For further examination of the claims, this limitation is interpreted as “pyrophosphoric acid salts, sodium pyrophosphate, potassium pyrophosphate,”.
Claim 12 recites the limitation “(R111 selected from hydrogen or the group consisting of lower alkyl (C1 – C10), -O- (oxygen), or direct bond” in lines 34-35, which is indefinite because it is unclear if “R111 selected from hydrogen or the group consisting of lower alkyl (C1 – C10), -O- (oxygen), or direct bond” is a limitation, abbreviation, or reference character since it is followed by a parenthesis, and it is unclear if “C1 – C10” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. For further examination of the claims, this limitation is interpreted as “wherein R111 is selected from hydrogen or the group consisting of C1 – C10 alkyl, -O- (oxygen), or direct bond”.
Claim 12 recites the limitation “R11 – comprises (selected from)” in line 36, which is indefinite because it is unclear if “selected from” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. For further examination of the claims, this limitation is interpreted as “R11 – is selected from”
Claim 12 recites the limitation “lower alkyl (C1 – C10)” in line 38, which is indefinite because it is unclear if “C1 – C10” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. For further examination of the claims, this limitation is interpreted as “C1 – C10 alkyl”.
Claim 12 recites the limitation “methylene group (optionally substituted)” in line 39, which is indefinite because it is unclear if “optionally substituted” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. For further examination of the claims, this limitation is interpreted as “methyl group that is optionally substituted”.
Claim 12 recites the limitation “lower alkyl (C1 – C10)” in line 42, which is indefinite because it is unclear if “C1 – C10” is a limitation, abbreviation, or reference character since it is enclosed in parentheses. For further examination of the claims, this limitation is interpreted as “C1 – C10 alkyl”.
Claim Rejections - 35 USC § 102
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 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, 2, 6, 8, and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Colquhoun et al. (US 2011/0040045 A1, cited in IDS).
Regarding claim 1, Calquhoun teaches a method comprising dissolving PAEK in a mixture of a suitable solvent and an acid, intermixing boron trifluoride-diethyl etherate and excess thiol with the PAEK mixture, using these materials in excess to promote compete reaction, allowing the reaction to proceed for a selected time period to ensure substantially complete conversion of the PAEK to a poly (aryl ether thioacetal), and removing the poly (aryl ether thioacetal) from the solution by precipitation [0042], wherein the PAEK is poly(aryl ether ketone) [0002], wherein the solvent comprises diethylether, tetrahydrofuran, dioxin, a chlorinated solvent, dichloromethane, trichloromethane, dichloroethane, or dichlorobenzene [0052], which reads on a process for modifying an aromatic polyether backbone, in particular for modifying an aromatic moiety of the aromatic polyether backbone, for obtaining a modified polyether comprising the steps of: a) providing at least one aromatic polyether to be modified in dissolved state in an inert organic solvent, b) adding at least one modification reagent, c) adding at least one catalyst, wherein the at least one catalyst is a boron trifluoride complex, d) carrying out the process until a desired degree of functionalization of said aromatic polyether backbone is reached, e) recovery of the modified aromatic polyether as claimed.
Regarding claim 2, Calquhoun teaches that the method comprises, intermixing boron trifluoride-diethyl etherate and excess thiol with the PAEK mixture, using these materials in excess to promote compete reaction, allowing the reaction to proceed for a selected time period to ensure substantially complete conversion of the PAEK to a poly (aryl ether thioacetal) [0042], and further reacting with solvent, N-bromosuccinimide (NBS), and an alcohol to form a substantially soluble poly (aryl ether acetal) [0014, 0046, 0040], which reads on wherein after step b) at least one second modification reagent is added as claimed.
Regarding claim 6, Calquhoun teaches that the method comprises allowing the reaction to proceed for a selected time period to ensure substantially complete conversion of the PAEK to a poly (aryl ether thioacetal), and removing the poly (aryl ether thioacetal) from the solution by precipitation, wherein precipitation is conducted in cold methanol [0042], which reads on wherein prior to step e) the reaction solvent replaced by workup solvent as claimed.
Regarding claim 8, Calquhoun teaches that the solvent comprises dichloromethane, trichloromethane, dichloroethane, or dichlorobenzene [0052], which reads on wherein the inert organic solvent is selected from halogenated hydrocarbons, or halogenated aromatics as claimed.
Regarding claim 9, Calquhoun teaches that the method comprises intermixing boron trifluoride-diethyl etherate and excess thiol with the PAEK mixture [0042], which reads on wherein the catalyst is selected from complexes of boron trifluoride with: ethers (diethyl ether) as claimed.
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.
Claims 1-3, 6-10, and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Klebe et al. (US 3,733,302 A, cited in IDS) in view of Colquhoun et al. (US 2011/0040045 A1, cited in IDS).
Regarding claims 1, 6, 8, 9, and 12, Klebe teaches passing boron trifluoride into a solution of a poly(2,6-diphenyl phenylene oxide) in chloroform and N-hydroxymethyl trimellitimide in a solvent mixture of chloroform and nitrobenzene, saturating the mixture with boron trifluoride, agitating the mixture, pouring the mixture into excess methanol, and recovering a product in quantitative yield, wherein the product is a poly(2,6-diphenyl phenylene oxide) polymer having about 5 mole percent of chemically combined trimellitimido methyl substituted diphenyl phenylene oxide units (5:67-75; 6:1-4), which reads on a process for modifying an aromatic polymer backbone, in particular for modifying an aromatic moiety of the aromatic polyether backbone, for obtaining a modified polyether comprising the steps of: a) providing at least one aromatic polyether to be modified in dissolved state in an inert organic solvent, b) adding at least one modification reagent, c) adding at least one catalyst, wherein the at least one catalyst is a boron trifluoride, d) carrying out the process until a desired degree of functionalization of said aromatic polyether backbone is reached, e) recovery of the modified aromatic polymer, wherein prior to stop e) the reaction solvent replaced by workout solvent, wherein said aromatic polyether comprises at least one of the following repeating units:
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wherein Ra and Rb represent substituents on the benzene ring and each independently comprises -arylene, wherein the inert organic solvent is selected from halogenated hydrocarbons, wherein the at least one modifying reagent is selected from compounds of the general structure 1 (GS1), wherein Fn is a functional moiety selected from structures of General formula 4 (GF4) wherein Sp is spacing moiety selected from structure of General formula 6 (GF6) wherein Lg is a leaving group moiety selected from structures of General formula 9 (GF9) in which R12 – comprises hydrogen, R13 and R14 independently each other comprises hydrogen, R21 – represents a substituent on the benzene ring and each independently comprises carboxyl group, and m represents an integer of 1.
Klebe does not teach that the at least one catalyst is a boron trifluoride complex and that the catalyst is selected from the claimed group. However, Colquhoun teaches intermixing boron trifluoride-diethyl etherate and excess thiol with a PAEK mixture that is obtained by dissolving PAEK in a mixture of a suitable solvent and an acid, using these materials in excess to promote compete reaction, allowing the reaction to proceed for a selected time period to ensure substantially complete conversion of the PAEK to a poly (aryl ether thioacetal), and removing the poly (aryl ether thioacetal) from the solution by precipitation [0042], wherein the PAEK is poly(aryl ether ketone) [0002], wherein the solvent comprises diethylether, tetrahydrofuran, dioxin, a chlorinated solvent, dichloromethane, trichloromethane, dichloroethane, or dichlorobenzene [0052]. Klebe and Colquhoun are analogous art because both references are in the same field of endeavor of a process for modifying an aromatic polyether backbone, in particular for modifying an aromatic moiety of the aromatic polyether backbone, for obtaining a modified polyether. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Colquhoun’s boron trifluoride-diethyl etherate to substitute for at least a fraction of Klebe’s boron trifluoride in Klebe’s method. The proposed modification would read on wherein the at least one catalyst is a boron trifluoride complex as claimed, wherein the catalyst is selected from complexes of boron trifluoride with ethers (diethyl ether) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying catalysis properties of Klebe’s method because Colquhoun teaches that the boron trifluoride-diethyl etherate is beneficial for being useful for intermixing it and excess thiol with a PAEK mixture that is obtained by dissolving PAEK in a mixture of a suitable solvent and an acid, using these materials in excess to promote compete reaction, allowing the reaction to proceed for a selected time period to ensure substantially complete conversion of the PAEK to a poly (aryl ether thioacetal), and removing the poly (aryl ether thioacetal) from the solution by precipitation [0042], wherein the PAEK is poly(aryl ether ketone) [0002], wherein the solvent comprises diethylether, tetrahydrofuran, dioxin, a chlorinated solvent, dichloromethane, trichloromethane, dichloroethane, or dichlorobenzene [0052], and because Klebe teaches that the boron trifluoride is a catalyst (1:19-20) that is used in a method comprising passing boron trifluoride into a solution of a poly(2,6-diphenyl phenylene oxide) in chloroform and N-hydroxymethyl trimellitimide in a solvent mixture of chloroform and nitrobenzene, saturating the mixture with boron trifluoride, agitating the mixture, pouring the mixture into excess methanol, and recovering a product in quantitative yield, wherein the product is a poly(2,6-diphenyl phenylene oxide) polymer having about 5 mole percent of chemically combined trimellitimido methyl substituted diphenyl phenylene oxide units (5:67-75; 6:1-4).
Regarding claim 2, Klebe teaches that the polymer having about 5 mole percent of chemically combined trimellitimide methyl substituted diphenyl phenylene oxide units is a polyimide, and that a solution of the polyimide in N-methyl pyrrolidone is diluted with water and neutralized with ammonium hydroxide solution (6:1-9), which reads on wherein after step b) at least one second modification reagent is added as claimed.
Regarding claims 3 and 10, Klebe teaches that the polymer having about 5 mole percent of chemically combined trimellitimide methyl substituted diphenyl phenylene oxide units is a polyimide, that a solution of 2 % of the polyimide in N-methyl-pyrrolidone is diluted with 25% of water, neutralized with 1 normal ammonium hydroxide solution, and that the polymer is electrodeposited on a copper electrode as described in another example (6:1-11), where in the other example, the polymer is electrodeposited on a copper electrode using a current, wherein the electrode is dried in order to remove all solvents, wherein the electrode is found to have a coating amount to the deposited polymer (5:16-22), which reads on wherein prior to step e) at least one catalyst quencher is added as claimed, wherein the catalyst quencher is selected from carboxylic acid amides, (N-methyl pyrrolidone) as claimed.
Claims 4, 5, and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Klebe et al. (US 3,733,302 A, cited in IDS) in view of Colquhoun et al. (US 2011/0040045 A1, cited in IDS) as applied to claim 1, and further in view of Ichinose et al. (JP 2020-037672 A, machine translation in English used for citation).
Regarding claims 4 and 11, Klebe in view of Colquhoun renders obvious the process according to claim 1 as explained above.
Klebe does not teach that at least one catalyst scavenger is added prior to step e) and that the scavenger is selected from the claimed group. However, Ichinose teaches sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride that is a catalyst that has the effect of accelerating a thermal polymerization reaction of a cyclic polyphenylene ether ether ketone composition [0083]. Ichinose teaches that a solid is obtained that is a compound consisting of phenylene ether ketone units and that is a cyclic polyphenylene ether ketone [0107], that boron trifluoride diethyl ether complex and 1,2-ethanedithiol are added to a mixture of the dry solid, dichloromethane, and trifluoroacetic acid, that the mixture is stirred at room temperature for approximately 18 hours, that the reaction mixture is dispersed in methanol, that the resulting solid is collected by filtration, and that a thiol-modified compound of polyphenylene ether ether ketone is obtained [0108]. Klebe and Ichinose are analogous art because both references are in the same field of endeavor of a process for modifying an aromatic polyether backbone in particular for modifying an aromatic moiety of the aromatic polyether backbone, for obtaining a modified polyether. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to synthesize Klebe’s poly(2,6-diphenyl phenylene oxide) in the presence of Ichinose’s catalyst that is sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride, and to use Ichinose’s catalyst that is sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride to modify Klebe’s solution of a poly(2,6-diphenyl phenylene oxide) in chloroform and N-hydroxymethyl trimellitimide. The proposed modification would read on wherein at least one catalyst scavenger is added prior to step e) as claimed, wherein the scavenger is selected from hydrofluoric acid salts (lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride) as claimed. One of ordinary skill in the art would have been motivated to do so because Ichinose teaches that the sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride is a catalyst that is beneficial for the effect of accelerating a thermal polymerization reaction of a cyclic polyphenylene ether ether ketone composition [0083], that a solid that is the compound consisting of phenylene ether ketone units and that is the cyclic polyphenylene ether ketone [0107] is beneficial for use in a method of adding boron trifluoride diethyl ether complex and 1,2-ethanedithiol to a mixture of the dry solid, dichloromethane, and trifluoroacetic acid, stirring the mixture at room temperature for approximately 18 hours, dispersing the reaction mixture in methanol, collected the resulting solid by filtration, and obtaining a thiol-modified compound of polyphenylene ether ether ketone [0108], which means that the proposed modification would have been beneficial for accelerating synthesis of Klebe’s poly(2,6-diphenyl phenylene oxide) and for improving yield of Klebe’s poly(2,6-diphenyl phenylene oxide).
Regarding claim 5, Klebe in view of Colquhoun renders obvious the process according to claim 1 as explained above. Klebe teaches that the polymer having about 5 mole percent of chemically combined trimellitimide methyl substituted diphenyl phenylene oxide units is a polyimide, that a solution of 2 % of the polyimide in N-methyl-pyrrolidone is diluted with 25% of water, neutralized with 1 normal ammonium hydroxide solution, and that the polymer is electrodeposited on a copper electrode as described in another example (6:1-11), where in the other example, the polymer is electrodeposited on a copper electrode using a current, wherein the electrode is dried in order to remove all solvents, wherein the electrode is found to have a coating amount to the deposited polymer (5:16-22), which reads on wherein prior to step e) catalyst quencher is added as claimed/
Klebe does not teach that prior to step e) catalyst scavenger is added. However, Ichinose teaches sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride that is a catalyst that has the effect of accelerating a thermal polymerization reaction of a cyclic polyphenylene ether ether ketone composition [0083]. Ichinose teaches that a solid is obtained that is a compound consisting of phenylene ether ketone units and that is a cyclic polyphenylene ether ketone [0107], that boron trifluoride diethyl ether complex and 1,2-ethanedithiol are added to a mixture of the dry solid, dichloromethane, and trifluoroacetic acid, that the mixture is stirred at room temperature for approximately 18 hours, that the reaction mixture is dispersed in methanol, that the resulting solid is collected by filtration, and that a thiol-modified compound of polyphenylene ether ether ketone is obtained [0108]. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to synthesize Klebe’s poly(2,6-diphenyl phenylene oxide) in the presence of Ichinose’s catalyst that is sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride, and to use Ichinose’s catalyst that is sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride to modify Klebe’s solution of a poly(2,6-diphenyl phenylene oxide) in chloroform and N-hydroxymethyl trimellitimide. The proposed modification would read on wherein prior to step e) catalyst scavenger is added, which therefore reads on wherein prior to step e) both catalyst quencher and catalyst scavenger are added as claimed. One of ordinary skill in the art would have been motivated to do so because Ichinose teaches that the sodium fluoride, potassium fluoride, cesium fluoride, or lithium chloride is a catalyst that is beneficial for the effect of accelerating a thermal polymerization reaction of a cyclic polyphenylene ether ether ketone composition [0083], that a solid that is the compound consisting of phenylene ether ketone units and that is the cyclic polyphenylene ether ketone [0107] is beneficial for use in a method of adding boron trifluoride diethyl ether complex and 1,2-ethanedithiol to a mixture of the dry solid, dichloromethane, and trifluoroacetic acid, stirring the mixture at room temperature for approximately 18 hours, dispersing the reaction mixture in methanol, collected the resulting solid by filtration, and obtaining a thiol-modified compound of polyphenylene ether ether ketone [0108], which means that the proposed modification would have been beneficial for accelerating synthesis of Klebe’s poly(2,6-diphenyl phenylene oxide) and for improving yield of Klebe’s poly(2,6-diphenyl phenylene oxide).
Correspondence
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/DAVID T KARST/Primary Examiner, Art Unit 1767
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