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US 2013/0131201 A1Published application
Superacid functional compounds
AssigneeArkema Inc.
InventorsJames T. Goldbach, Xiaobo Wan, David A. Mountz
Life of this patent
Estimating the term…
Abstract
The invention relates to a novel synthesis method for forming superacid functional molecules that include monomers, as well as new polymers and copolymers formed from the monomers, and uses for these superacid molecules, polymers, and copolymers. The superacid molecules have an alpha,alpha-difluorosulfonic acid functionality that can be obtained by a reaction between various Grignard reagents and an alkyl(2-fluorosulfonyl)-1,1-difluoroacetate, such as methyl(2-fluorosulfonyl-1,1-difluoroacetate. The molecules, polymers and copolymers would be expected to have enhanced ion conductivity, and would be useful in a variety of applications, including as ion-conductive materials, surfactants, and ion exchange resins.
Claims22
A composition having the following formula:
- where:
- D=a bond, aryl, substituted aryl, alkyl, alkeneyl, alkynyl, fluoro or perfluoro analogues thereof of C1 to C32,
- R3=hydrogen, vinylic, alkyl, alkeneyl, alkynyl, fluoro or perfluoro analogues thereof of C1 to C32,
- R2=a group selected from the group consisting of sulfonate, sulfinate, sulfonyl halide, phosphonate, phosphinate, and carboxylate, and has a counterion, M+, associated with it which is an alkali, alkaline earth, transition metal cation, or organic counterion.
1 more element
A composition having the formula:
- where:
- R4=alkyl, alkeneyl, alkynyl, aryl, fluoro or perfluoro analogues thereof of C1 to C32,
- R2—a group selected from the group consisting of sulfonate, sulfinate, sulfonyl halide, phosphonate, phosphinate, and carboxylate, and has a counterion, M+, associated with it which is an alkali, alkaline earth, transition metal cation, or organic counterion.
A homopolymer or copolymer composition having the formula:
- where:
- D=a bond, aryl, substituted aryl, alkyl, alkeneyl, alkynyl, fluoro or perfluoro analogues thereof of C1 to C32
- R2=a group selected from the group consisting of sulfonate, sulfinate, sulfonyl phosphonate, phosphinate, and carboxylate, and has a counterion, M+, associated with it which is an alkali, alkaline earth, transition metal cation, or organic counterion.
- A=a group capable of promoting cross-linking including alkene, alkylketone, aryl, alkyl or aryl ester, alkyl or aryl amide, hydroxyl, amine, epoxide, aldehyde, isocyanate, carboxylic, acid, fluoro or perfluoro, or multifunctional analogues thereof,
- m=0 to 19,998,
- n=2 to 20,000,
- the ratio of n to m=from 1 to 99%, and the value of n+m=2 to 20,000
4 more elements
A process for forming a super acid, as illustrated below,
- comprising the step of reacting an organometallic component (1) with a reagent hearing at least one functional group chosen from:
- sulfonyl halide, sulfonic acid, sulfonate salt, and at least one functional group chosen from:
- carboxylic acid, carboxylate ester, carboxylic;
- salt (2);
- to produce as the primary product a compound (3) bearing an organic fragment from reagent (1), a ketone functionality, an organic fragment from reagent (2), and at least one functional group chosen from:
- sulfonyl halide, sulfonic acid, or sulfonate salt;
- where:
- R5=a proton, an alkali metal cation, and alkali earth metal cation, a transition metal cation, and organic cation or an aliphatic, aromatic-aliphatic, or alicyclic hydrocarbon radical, alkenyl, alkynyl or aryl group (or fluoro or perfluoro analogue thereof) of C1 to C32.
- R6=R5 or a different aliphatic, aromatic-aliphatic, or alicyclic hydrocarbon radical, alkenyl, alkynyl or aryl group (or fluoro or perfluoro analogue thereof) of C1 to C32.
- X1=alkaline earth or transition metal, alone or bound or coordinated to a halide (F, Cl, Br, I) or other appropriate counterion.
- R2=a group selected from the group consisting of sulfonate, sulfinate, sulfonyl halide, phosphonate, phosphinate, and carboxylate, and has a counterion, M+, associated with it which is a proton, alkali, alkaline earth, transition metal cation, or organic counterion.
8 more elements
A reaction process, as illustrated below,
- comprising reacting an organometallic, or inorganic or organic reducing agent component (1) with a reagent bearing at least one functional group chosen from:
- sulfonyl halide, sulfonic acid, and sulfonate salt, and at least one functional group chosen from:
- carboxylic acid, carboxylate ester, and carboxylic salt (2), to form as the primary product a compound (3) bearing an acetal functionality, a difluoromethyl fragment from reagent (2), and at least one functional group chosen from:
- sulfonyl halide, sulfonic acid, or sulfonate salt.
- where:
- R5=a proton, an alkali metal cation, and alkali earth metal cation, a transition metal cation, and organic cation or an aliphatic, aromatic-aliphatic, or alicyclic hydrocarbon radical, alkenyl, alkynyl or aryl group (or fluoro or perfluoro analogue thereof) of C1 to C32,
- R2=a group chosen from sulfonate, sulfinate, sulfonyl halide, phosphonate, phosphinate, or carboxylate, and has a counterion, M+, associated with it which is an alkali, alkaline earth, transition metal cation, or organic counterion,
- R6=R5 or a proton, an alkali metal cation, and alkali earth metal cation, a transition metal cation, and organic cation or an aliphatic, aromatic-aliphatic, or alicyclic hydrocarbon radical, alkenyl, alkynyl or aryl group (or fluoro or perfluoro analogue thereof) of C1 to C32,
- X2=an inorganic or organic reducing agent.
6 more elements
Dependencies are inferred from the claim text.