Crosslinkable fluorinated elastomer composition and crosslinked product thereof

Patent metadata

Field	Value
Publication number	US-2016137809-A1
Application number	US-201615007690-A
Country	US
Kind code	A1
Filing date	Jan 27, 2016
Priority date	Aug 7, 2013
Publication date	May 19, 2016
Grant date	—

Abstract

To provide a crosslinkable fluorinated elastomer composition which is excellent in crosslinking reactivity and of which a crosslinked product is excellent in heat resistance and chemical resistance. The crosslinkable fluorinated elastomer composition comprises a fluorinated elastomer (e.g. a tetrafluoroethylene/perfluoro(alkyl vinyl ether) copolymer) and an aromatic compound having at least two crosslinkable unsaturated double bonds (e.g. a compound represented by the formula (A-1)), and the crosslinked product is one obtained by crosslinking the crosslinkable fluorinated elastomer composition.

First claim

What is claimed is:

1 . A crosslinkable fluorinated elastomer composition, characterized by comprising a fluorinated elastomer and an aromatic compound having at least two crosslinkable unsaturated double bonds.

2 . The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the aromatic compound having at least two crosslinkable unsaturated double bonds, has at least two vinyl groups or allyl groups bonded to an aromatic ring.

3 . The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the aromatic compound having at least two crosslinkable unsaturated double bonds, comprises either one or both of a fluorinated aromatic compound having at least two of group (1) represented by the following formula (1) and an aromatic hydrocarbon having at least two vinyl groups bonded to an aromatic ring:

wherein s is 0 or 1, and each of R 1 , R 2 , R 3 and R 4 which are independent of one another, is a hydrogen atom or a fluorine atom.

4 . The crosslinkable fluorinated elastomer composition according to claim 3 , wherein the fluorinated aromatic compound comprises a fluorinated aromatic compound having at least two of said group (1), and the fluorinated aromatic compound having at least two of said group (1) comprises either one or both a fluorinated aromatic compound (A) represented by the following formula (A) and a fluorinated aromatic compound (B) having said group (1) and an ether bond, obtained by subjecting a fluorinated aromatic compound (x) represented by the following formula (x), either one or both of an aromatic compound (y1) having said group (1) and a phenolic hydroxy group and an aromatic compound (y2) having said group (1) and a fluorine atom substituting an aromatic ring, and an aromatic compound (z) having at least three phenolic hydroxy groups, to a condensation reaction in the presence of a HF elimination agent:

wherein, n is an integer of from 0 to 6, a is an integer from 0 to 5, b is an integer of from 0 to 4, c is an integer of from 0 to 4, a+c+n is from 2 to 6, a+b is from 2 to 9, Z is a single bond, —O—, —S—, —CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —SO— or —SO 2 —, Rf 1 is a C 1-8 fluoroalkyl group, each of Y 1 and Y 2 which are independent of each other, is said group (1), and F in the aromatic ring represents that hydrogen atoms of the aromatic ring are all substituted by fluorine atoms,

wherein N is an integer of from 0 to 3, each of d and e which are independent of each other, is an integer of from 0 to 3, each of Rf 2 and Rf 3 which are independent of each other, is a C 1-8 fluoroalkyl group, and F in the aromatic ring represents that hydrogen atoms of the aromatic ring are all substituted by fluorine atoms.

5 . The crosslinkable fluorinated elastomer composition according to claim 4 , wherein the fluorinated aromatic compound (x) is at least one member selected from the group consisting of perfluorobenzene, perfluorotoluene, perfluoroxylene, perfluorobiphenyl, perfluoroterphenyl, a perfluorotriphenyl benzene, a perfluorotetraphenyl benzene, a perfluoropentaphenyl benzene and a perfluorohexaphenylbenzene.

6 . The crosslinkable fluorinated elastomer composition according to claim 4 , wherein the aromatic compound (z) is at least one member selected from the group consisting of trihydroxybenzene, trihydroxybiphenyl, trihydroxynaphthalene, 1,1,1-tris(4-hydroxyphenyl)ethane, tris(4-hydroxyphenyl)benzene, tetrahydroxybenzene, tetrahydroxybiphenyl, tetrahydroxybinaphthyl and a tetrahydroxyspiroindane.

7 . The crosslinkable fluorinated elastomer composition according to claim 4 , wherein the fluorinated aromatic compound (A) is one which satisfies both conditions
that each of R 1 , R 2 , R 3 and R 4 in Y 1 and Y 2 in the formula (A) is a hydrogen atom, and that in the formula (A), c is 0, or c is an integer of from 1 to 4 and Rf 1 is a 01-8 perfluoroalkyl group.

8 . The crosslinkable fluorinated elastomer composition according to claim 7 , wherein the fluorinated aromatic compound (A) is a compound represented by the following formula (A-1) or (A-2):

9 . The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the content of the aromatic compound having at least two crosslinkable unsaturated double bonds, is from 0.1 to 15 mass % based on the mass of the fluorinated elastomer.

10 . The crosslinkable fluorinated elastomer composition according to claim 1 , which further contains an organic peroxide, and wherein the content of the organic peroxide is from 0.1 to 5 mass % based on the mass of the fluorinated elastomer.

11 . The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the fluorinated elastomer contains iodine and/or bromine atoms.

12 . The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the fluorinated elastomer is a perfluoroelastomer.

13 . The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the fluorinated elastomer is a tetrafluoroethylene/perfluoro(alkyl vinyl ether) copolymer having an iodine atom at a polymer chain terminal.

14 . The crosslinkable fluorinated elastomer composition according to claim 1 , which further contains a crosslinking aid other than the aromatic compound having at least two crosslinkable unsaturated double bonds, and wherein the content of the crosslinking aid is from 0.1 to 3 mass % based on the mass of the fluorinated elastomer.

15 . The crosslinkable fluorinated elastomer composition according to claim 14 , wherein the mass ratio of the aromatic compound having at least two crosslinkable unsaturated double bonds/the crosslinking aid other than the aromatic compound is from 1/30 to 150/1.

16 . The crosslinkable fluorinated elastomer composition according to claim 14 , wherein the crosslinking aid other than the aromatic compound having at least two crosslinkable unsaturated double bonds is triallyl isocyanurate.

17 . A crosslinked product obtained by crosslinking the crosslinkable fluorinated elastomer composition as defined in claim 1 .

Assignees

• Asahi Glass Co Ltd

Inventors

• Kunimoto Akinobu
• Yamamoto Hiromasa
• Sugiyama Norihide
• Yamada Takeshi

Classifications

• C08K5/06 Primary

  Ethers; Acetals; Ketals; Ortho-esters · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title