Superacid functional compounds

Patent metadata

Field	Value
Publication number	US-9708254-B2
Application number	US-201113813510-A
Country	US
Kind code	B2
Filing date	Aug 1, 2011
Priority date	Aug 6, 2010
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

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.

First claim

What is claimed is:

1. A vinylic monomer for free-radical polymerization having the following formula:

where:
D=a bond,
R 3 =R 3 =C 2-32 vinylic, C 2-32 alkenyl, C 2-32 alkynyl, C 2-32 aryl and fluoro or perfluoro analogues of said C 2-32 vinylic, aryl, alkenyl, or alkynyl groups, capable of forming a polymer using a free-radical initiator,
R 2 =a group selected from the group consisting of sulfonate, sulfinate, sulfonyl halide, and carboxylate, and has a counterion, M + , associated with it which is an alkali, alkaline earth, transition metal cation, or organic counterion.

2. The vinylic monomer of claim 1 having the following formula:

where:
R 1 =independently is hydrogen, aliphatic, aromatic, or alicyclic hydrocarbon radical, alkenyl, alkynyl or aryl group wherein said alkenyl, alkynyl or aryl group is of C 1 to C 16 , and the fluoro or perfluoro analogues of said C 1 to C 16 aryl, alkenyl or alkynyl groups, and wherein at least one of the R 1 groups is vinylic.

3. The vinylic monomer of claim 2 where one of the groups, R 1 , is vinylic, and the other groups R 1 are hydrogen.

4. The vinylic monomer of claim 1 where R 2 is chosen from: sulfonyl halide, sulfonate, or sulfinate.

5. The vinylic monomer of claim 2 where one of the groups, R 1 , is vinylic, the other groups R 1 are hydrogen, and R 2 is sulfonyl halide or sulfonate.

Assignees

• Goldbach James T
• Wan Xiaobo
• Mountz David A
• Arkema Inc

Inventors

• Goldbach James T
• Wan Xiaobo
• Mountz David A

Classifications

• C08F216/36

  by a ketonic radical · CPC title

• C08F12/24

  Phenols or alcohols · CPC title

• C07F9/3808

  Acyclic saturated acids which can have further substituents on alkyl · CPC title

• C07C323/22 Primary

  containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• C07C309/84

  of a carbon skeleton substituted by carboxyl groups · CPC title