Mixture of polyfluoroalkene carboxylic acids or salts thereof and process for producing the same

Patent metadata

Field	Value
Publication number	US-9873654-B2
Application number	US-201515329192-A
Country	US
Kind code	B2
Filing date	Jul 28, 2015
Priority date	Aug 8, 2014
Publication date	Jan 23, 2018
Grant date	Jan 23, 2018

Abstract

A mixture of polyfluoroalkene carboxylic acids or salts thereof represented by the general formulas:

C n F 2n+1 CH═CF(CF 2 CF 2 ) m CF 2 COOM

and

C n−1 F 2n−1 CF═CHCF 2 (CF 2 CF 2 ) m CF 2 COOM

wherein M is a hydrogen atom, an ammonium salt, an organic amine salt or an alkali metal, n is an integer of 1 to 6 and m is an integer of 0 to 2. The mixture of polyfluoroalkene carboxylic acids or salts thereof is produced by subjecting a polyfluoroalkane carboxylic acids represented by the general formula:

C n F 2n+1 (CH 2 CF 2 )(CF 2 CF 2 ) m CF 2 COOH

to a dehydrofluorination reaction in the presence of a nitrogen-containing heterocyclic compound catalyst, and has a lower critical micelle concentration and less surface tension at that time, therefore, the mixture of polyfluoroalkene carboxylic acids or salts thereof can be effectively used as a surfactant in the polymerization of fluorine-containing monomers.

First claim

The invention claimed is:

1. A mixture of polyfluoroalkene carboxylic acids or salts thereof corresponding to the general formulas:
C n F 2n+1 CH═CF(CF 2 CF 2 ) m CF 2 COOM

and
C n−1 F 2n−1 CF═CHCF 2 (CF 2 CF 2 ) m CF 2 COOM

wherein M is a hydrogen atom, an ammonium salt, an organic amine salt or an alkali metal, n is an integer of 1 to 6 and m is an integer of 0 to 2.

2. A process for producing a mixture of polyfluoroalkene carboxylic acids corresponding to the general formulas:
C n F 2n+1 CH═CF(CF 2 CF 2 ) m CF 2 COOH

and
C n−1 F 2n−1 CF═CHCF 2 (CF 2 CF 2 ) m CF 2 COOH

wherein n is an integer of 1 to 6 and m is an integer of 0 to 2,
which comprises subjecting a polyfluoroalkane carboxylic acids corresponding to the general formula:
C n F 2n+1 (CH 2 CF 2 )(CF 2 CF 2 ) m CF 2 COOH

wherein n is an integer of 1 to 6 and m is an integer of 0 to 2, to a dehydrofluorination reaction in the presence of a nitrogen-containing heterocyclic compound catalyst,
wherein the nitrogen-containing heterocyclic compound used as a catalyst is 1,8-diazabicyclo[5.4.0]undec-7-ene or 1,5-diazabicyclo[4.3.0]non-5-ene.

3. A process for producing a mixture of polyfluoroalkene carboxylic acid salts, which comprises reacting a mixture of polyfluoroalkene carboxylic acids obtained by the production process according to claim 2 with an ammonia, an organic amine or an alkali metal hydroxide.

4. In a process for conducting a polymerization reaction of fluorine-containing monomer the improvement comprising contacting a mixture of polyfluoroalkene carboxylic acids or salts thereof according to claim 1 , as an emulsifying agent, with a polymerization mixture.

5. In a process for conducting a polymerization reaction of fluorine-containing monomer the improvement comprising contacting a mixture of polyfluoroalkene carboxylic acids or salts thereof according to claim 1 , as an emulsifying agent and/or a dispersing agent, with a polymerization mixture.

Assignees

• Unimatec Co Ltd

Inventors

• Oda Yuichiro
• Negishi Ryota

Classifications

• C07C51/377 Primary

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} · CPC title

• C07C57/52 Primary

  containing halogen · CPC title

• C08F2/18

  Suspension polymerisation · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title

• C07C51/412

  by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part · CPC title