Functionalized triazine compounds, compositions comprising such compounds and cured fluoropolymer articles

Patent metadata

Field	Value
Publication number	US-12168647-B2
Application number	US-202017615155-A
Country	US
Kind code	B2
Filing date	Jun 22, 2020
Priority date	Jun 28, 2019
Publication date	Dec 17, 2024
Grant date	Dec 17, 2024

Abstract

Described herein are compounds according to Formula (I) wherein Rf is a perfluorinated divalent group comprising 2 to 12 carbon atoms; and Z is selected from —CH═CH 2 , and —CH 2 CH═CH. A method of making the compound from a functionalized vinyl ether and ammonia is disclosed. In one embodiment, the functionalized triazine-containing compound is used in the polymerization of a fluoropolymer. In another embodiment, the functionalized triazine-containing compound is used in a curable fluoropolymer composition and cured to form articles.

First claim

What is claimed is:

1. A curable composition comprising (a) a fluorinated elastomeric gum comprising a fluoropolymer, wherein the fluoropolymer comprises a —I cure site, a —Br cure site, a —CN cure site, or combinations thereof; (b) a peroxide; and (c) a compound of Formula (I)

wherein Rf is a perfluorinated divalent group comprising 2 to 12 carbon atoms, and Z is —CH═CH 2 , or —CH 2 CH═CH 2 .

2. The curable composition of claim 1 , wherein the molecular weight of the compound of Formula (I) is less than 1500 grams/mole.

3. The curable composition of claim 1 , wherein Rf is a —(CF 2 ) n —, where n is an integer from 2 to 8.

4. The curable composition of claim 1 , wherein Rf comprises —(CF 2 ) p —O—(CF 2 ) q —, —(OCF 2 CF 2 ) q —, —(OCF 2 CF(CF 3 )) p — —(CF 2 CF(CF 3 )) p —O—(CF 2 ) q —, or combinations thereof, wherein p is an integer of 2 to 11 and q is an integer from 2 to 11, such that the sum of p+q is 2 to 12.

5. The curable composition of claim 1 , wherein the compound according to Formula (I) is at least one of the following: [Br—(CF 2 ) 4 OCFH] 3 —C 3 N 3 , [I—(CF 2 ) 4 OCFH] 3 —C 3 N 3 , [CH 2 ═CH—(CF 2 ) 4 OCFH] 3 —C 3 N 3 , [CH 2 ═CHCH 2 —(CF 2 ) 4 OCFH] 3 —C 3 N 3 , [CH 2 ═CH—(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH] 3 —C 3 N 3 , [CH 2 ═CHCH 2 —(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH] 3 —C 3 N 3 , [Br—(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH] 3 —C 3 N 3 , and [I—(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH] 3 —C 3 N 3 , where C 3 N 3 represents the triazine ring.

6. The curable composition of claim 1 , comprising at least 0.05 part by weight of the compound of Formula (I) to 100 parts by weight of the fluoropolymer.

7. The curable composition of claim 1 , wherein the peroxide comprises 2,5-dimethyl-2,5-di(t-butylperoxy)hexane; dicumyl peroxide; di(2-t-butylperoxyisopropyl)benzene; dialkyl peroxide; bis (dialkyl peroxide); 2,5-dimethyl-2,5-di(tertiarybutylperoxy) 3 -hexyne; dibenzoyl peroxide; 2,4-dichlorobenzoyl peroxide; tertiarybutyl perbenzoate; α,α′-bis(t-butylperoxy-diisopropylbenzene); t-butyl peroxy isopropylcarbonate, t-butyl peroxy 2-ethylhexyl carbonate, t-amyl peroxy 2-ethylhexyl carbonate, t-hexylperoxy isopropyl carbonate, di[1,3-dimethyl-3-(t-butylperoxy)butyl] carbonate, carbonoperoxoic acid, O,O′-1,3-propanediyl OO,OO′-bis(1,1-dimethylethyl) ester, or combination thereof.

8. The curable composition of claim 1 , wherein the fluoropolymer comprises: (i) a copolymer comprising tetrafluoroethylene, vinylidene fluoride, and hexafluoropropylene monomeric units; (ii) a copolymer comprising tetrafluoroethylene, and propylene monomeric units; (iii) a copolymer comprising tetrafluoroethylene, vinylidene fluoride, and propylene monomeric units; and (iv) a copolymer comprising vinylidene fluoride, perfluoro (methyl vinyl) ether, and hexafluoropropylene monomeric units; (v) a copolymer comprising tetrafluoroethylene, vinyl fluoride, and hexafluoropropylene monomeric units; (vi) a copolymer comprising vinyl fluoride, perfluoro (methyl vinyl) ether, and hexafluoropropylene monomeric units; (vii) a copolymer of tetrafluoroethylene with perfluorovinyl ether, (viii) a copolymer of tetrafluoroethylene with perfluoroallyl ether, or combinations thereof.

9. The curable composition of claim 1 , comprising at least 0.05 parts by weight of the peroxide per 100 parts of the fluoropolymer.

10. A cured article derived from the curable composition of claim 1 .

11. The cured article of claim 10 , wherein the article is an o-ring, a seal, a gasket, a hose or a sheet.

12. A compound according to Formula (I):

wherein Rf is a perfluorinated divalent group comprising 2 to 12 carbon atoms; and Z is —I, —Br, —CH═CH 2 , or —CH 2 CH═CH 2 .

13. The compound of claim 12 , wherein Rf is —(CF 2 ) m —, where m is an integer from 2 to 8.

14. The compound of claim 12 , wherein Rf comprises at least one catenated oxygen or nitrogen atom.

15. The compound of claim 12 , wherein Formula (I) is: (Br(CF 2 ) 4 OCFH) 3 —C 3 N 3 , (I(CF 2 ) 4 OCFH) 3 —C 3 N 3 , (CH 2 ═CH(CF 2 ) 4 OCFH) 3 —C 3 N 3 , (CH 2 ═CHCH 2 (CF 2 ) 4 OCFH) 3 —C 3 N 3 , (CH 2 ═CHC(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH) 3 —C 3 N 3 , (CH 2 ═CHCH 2 (CF 2 ) 2 OCF(CF 3 )CF 2 OCFH) 3 —C 3 N 3 , (Br(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH) 3 —C 3 N 3 , (I(CF 2 ) 2 OCF(CF 3 )CF 2 OCFH) 3 —C 3 N 3 , or combinations thereof, where C 3 N 3 represents the triazine ring.

16. A fluoropolymer derived from (a) a fluorinated monomer, and (b) a compound of Formula (I)

wherein Rf is a perfluorinated divalent group comprising 2 to 12 carbon atom; and Z is —Br, —CH═CH 2 , or —CH 2 CH═CH 2 .

17. The fluoropolymer of claim 16 , further derived from a bisolefin monomer.

18. The fluoropolymer of claim 16 , wherein Z is —CH═CH 2 , or —CH 2 CH═CH 2 and the polymer is derived from less than 1.0 moles of the compound according to Formula (I).

Assignees

• 3M Innovative Properties Company

Inventors

• Mitchell Michael H
• Fukushi Tatsuo
• Guerra Miguel A
• Qiu Zai-Ming
• Roop Justin T

Classifications

• C08K5/3492

  Triazines · CPC title

• C08K5/14

  Peroxides · CPC title

• C07D251/24 Primary

  to three ring carbon atoms · CPC title

• C08L27/20

  Homopolymers or copolymers of hexafluoropropene · CPC title

• C08L29/10 Primary

  Homopolymers or copolymers of unsaturated ethers (C08L35/08 takes precedence) · CPC title