Curative compositions, fluoropolymer compositions, and methods

Patent metadata

Field	Value
Publication number	US-2016115294-A1
Application number	US-201414897155-A
Country	US
Kind code	A1
Filing date	Jun 11, 2014
Priority date	Jun 13, 2013
Publication date	Apr 28, 2016
Grant date	—

Abstract

A curative composition includes a tetraalkylphosphonium or tetraalkylammonium cation and an anion represented by Formula (Rf) 3 CO − , wherein each Rf is independently perfluoroalkyl having up to 12 carbon atoms. A fluoropolymer composition includes the curative composition and a fluoropolymer. The fluoropolymer can be an amorphous, curable fluoropolymer with nitrogen-containing cure sites. Shaped articles including the fluoropolymer, a method of making a fluoroelastomer article, and a method of making the curative composition are also described.

First claim

1 . A curative composition comprising a tetraalkylphosphonium or tetraalkylammonium cation and an anion represented by Formula

wherein each Rf is independently perfluoroalkyl having up to 12 carbon atoms.

2 . The curative composition of claim 1 , wherein each Rf is independently perfluoroalkyl having up to 4 carbon atoms.

3 . The curative composition of claim 1 , wherein each Rf is perfluoromethyl.

4 . The curative composition of claim 1 , wherein the tetraalkylphosphonium cation is tetrabutylphosphonium, and wherein the tetraalkylammonium cation is tetramethylammonium.

5 . The curative composition of claim 1 , wherein the curative composition comprises tetrabutylphosphonium perfluoro-tert-butoxide.

6 . The curative composition of claim 1 , wherein the curative composition is essentially free of hydrocarbon alcohol.

7 . A fluoropolymer composition comprising the curative composition of claim 1 and a fluoropolymer.

8 . The fluoropolymer composition of claim 7 , wherein the fluoropolymer is an amorphous, curable fluoropolymer with nitrogen-containing cure sites.

9 . The fluoropolymer composition of claim 8 , wherein the nitrogen-containing cure sites are nitrile-containing cure sites.

10 . The fluoropolymer composition of claim 7 , wherein the fluoropolymer comprises interpolymerized units of tetrafluoroethylene and at least one of a different perfluorinated olefin, a partially fluorinated olefin, a non-fluorinated olefin, a perfluoroalkylvinylether, or a perfluoroalkoxyalkylvinylether.

11 . The fluoropolymer composition of claim 10 , wherein the interpolymerized units further comprise at least one of perfluoro(8-cyano-5-methyl-3,6-dioxa-1-octene), CF 2 ═CFO(CF 2 ) L CN, CF 2 ═CFO(CF 2 ) u OCF(CF 3 )CN, CF 2 ═CFO[CF 2 CF(CF 3 )] q (CF 2 O) y CF(CF 3 )CN, or CF 2 ═CF[OCF 2 CF(CF 3 )] r O(CF 2 )CN, wherein L is in a range from 2 to 12; u is in a range from 2 to 6; q is in a range from 0 to 4; y is in a range from 0 to 6; r is in a range from 1 to 2; and t is in a range from 1 to 4.

12 . The fluoropolymer composition of claim 7 , further comprising at least one of a fluoropolymer filler, carbon black, or silica.

13 . The fluoropolymer composition of claim 7 , further comprising at least one of an ammonia-generating compound, a substituted triazine derivative, an unsubstituted triazine derivative, a peroxide, a bis-aminophenol, a bis-amidooxime, an organotin compound, or an amidine, bis-amidine, tris-amidine, tetra-amidine, or a salt thereof.

14 . A shaped article comprising the fluoropolymer composition of claim 7 .

15 . A method of making a fluoroelastomer article comprising:
providing the fluoropolymer composition of claim 7 , shaping the fluoropolymer composition; and crosslinking the fluoropolymer composition to form the fluoroelastomer article.

16 . A method of making the curative composition of claim 1 , the method comprising making the cation and the anion by
combining an alcohol represented by formula (Rf) 3 COH and a tetraalkyl phosphonium hydroxide or a tetraalkylammonium hydroxide; or combining an alcohol represented by formula (Rf) 3 COH, a base, and a tetraalkylphosphonium halide or a tetraalkylammonium halide.

17 . The method of claim 18 , wherein either the alcohol represented by formula (Rf) 3 COH and the tetraalkyl phosphonium or tetraalkylammonium hydroxide or a fluorinated alkoxide generated from the alcohol represented by formula (Rf) 3 COH and the base and the tetraalkylphosphonium or tetraalkylammonium halide are combined in a composition comprising a fluoropolymer.

18 . The method of claim 18 , wherein combining an alcohol represented by formula (Rf) 3 COH and a tetraalkylphosphonium or tetraalkylammonium hydroxide or combining an alcohol represented by formula (Rf) 3 COH, a base, and a tetraalkylphosphonium or tetraalkylammonium halide is carried out in a reaction medium that is essentially free of a hydrocarbon alcohol.

19 . The curative composition of claim 1 , wherein each alkyl independently has up to four carbon atoms.

20 . The curative composition of claim 1 , wherein the curative composition comprises tetramethylammonium perfluoro-tert-butoxide.

Assignees

• 3M Innovative Properties Co

Inventors

• Grootaert Werner M A

Classifications

• C08K5/50

  Phosphorus bound to carbon only · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title

• C08K5/0025 Primary

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08K5/19

  Quaternary ammonium compounds · CPC title

• C08J7/12

  Chemical modification · CPC title