IP Library Granted Patent US 10,066,077
Granted Patent B2
US 10,066,077 · App. 15/007,690 · Granted Sep 4, 2018

Crosslinkable fluorinated elastomer composition and crosslinked product thereof

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Quick Facts
Patent No.
US 10,066,077
App. No.
15/007,690
Granted
Sep 4, 2018
Kind
B2
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.

Claims (23)

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

wherein the aromatic compound having at least two crosslinkable unsaturated double bonds, comprises a fluorinated aromatic compound having at least two of group (1) represented by the following formula (1):

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,

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,

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.

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 further comprises an aromatic hydrocarbon having at least two vinyl groups bonded to an aromatic ring.

4. The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the fluorinated aromatic compound (x) is at least one selected from the group consisting of perfluorobenzene, perfluorotoluene, perfluoroxylene, perfluorobiphenyl, perfluoroterphenyl, a perfluorotriphenyl benzene, a perfluorotetraphenyl benzene, a perfluoropentaphenyl benzene and a perfluorohexaphenylbenzene.

5. The crosslinkable fluorinated elastomer composition according to claim 1 , wherein the aromatic compound (z) is at least one 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.

6. The crosslinkable fluorinated elastomer composition according to claim 1 , 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 C 1-8 perfluoroalkyl group.

7. The crosslinkable fluorinated elastomer composition according to claim 6 , wherein the fluorinated aromatic compound (A) is a compound represented by the following formula (A-1) or (A-2):

8. The crosslinkable fluorinated elastomer composition according to claim 1 , further comprising 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.

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

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

11. 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.

12. The crosslinkable fluorinated elastomer composition according to claim 1 , further comprising 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.

13. The crosslinkable fluorinated elastomer composition according to claim 12 , 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.

14. The crosslinkable fluorinated elastomer composition according to claim 12 , wherein the crosslinking aid other than the aromatic compound having at least two crosslinkable unsaturated double bonds is triallyl isocyanurate.

15. A crosslinked product obtained by crosslinking the crosslinkable fluorinated elastomer composition according to claim 1 .

Assignments (2)
CHANGE OF NAME Recorded Aug 7, 2018
From: ASAHI GLASS COMPANY, LIMITED
To: AGC INC.
Reel/Frame 046730/0786 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2016
From: KUNIMOTO, AKINOBU; YAMAMOTO, HIROMASA; SUGIYAMA, NORIHIDE; YAMADA, TAKESHI
To: ASAHI GLASS COMPANY, LIMITED
Reel/Frame 037597/0814 →