Novel fluorovinyl ether cure site monomers and fluoroelastomer copolymer compositions thereof
AssigneeDuPont Dow Elastomers L.L.C.
InventorsMing-Hong Hung, Walter W. Schmiegel
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Abstract
Disclosed herein is a novel class of fluorovinyl ether monomers which are useful as cure site monomers in fluoroelastomers, a process for the preparation of these fluorovinyl ether monomers, and fluoroelastomer copolymer compositions that contain copolymerized units of these fluorovinyl ether monomers.
Claims28
A fluorovinyl ether monomer having the formula CF3CHFCF2—(O)n—(CH2)m—(CF2)p—RfOCF═CF2, wherein Rf is a C1-C8 perfluoroalkyl group or a C1-C8 perfluoroalkoxy group, n is 0 or 1, m is an integer from 1 to 3, and p is an integer from 1 to 4.
A process for the preparation of a fluorovinyl ether monomer having the formula CF3CHFCF2—(O)n—(CH2)m—(CF2)p—RfOCF═CF2, wherein Rf is a C1-C8 perfluoroalkyl group or a C1-C8 perfluoroalkoxy group, n is 0 or 1, m is an integer from 1 to 3, and p is an integer from 1 to 4;
- said process comprising the steps of:
- A. chlorinating an hydroxy vinyl ether compound of the formula HO—(CH2)m—(CF2)p—RfOCF═CF2 to produce a chlorinated hydroxy ether of the formula HO—(CH2)m—(CF2)p—RfOCFCl—CF2Cl;
- B. condensing said chlorinated hydroxy ether with hexafluoropropene to produce a chlorinated ether of the formula CF3CHFCF2—(O)n—(CH2)m—(CF2)p—RfOCFCl—CF2Cl;
- and
- C. dechlorinating said chlorinated ether to produce a fluorinated vinyl ether of the formula CF3CHFCF2—(O)n—(CH2)m—(CF2)p—Rf—OCF═CF2.
A fluoroelastomer copolymer comprising:
- A. copolymerized units of a first monomer, said first monomer being a fluoroolefin selected from the group consisting of vinylidene fluoride and tetrafluoroethylene;
- B. copolymerized units of a second monomer, different from said first monomer, said second monomer selected from the group consisting of i) fluoroolefins, ii) hydrocarbon olefins, iii) perfluoro(alkyl vinyl)ethers and iv) perfluoro(alkoxy vinyl) ethers;
- and
- C. copolymerized units of a fluorinated vinyl ether cure site monomer of the formula CF3CHFCF2—(O)n—(CH2)m—(CF2)p—RfOCF═CF2, wherein Rf is a C1-C8 perfluoroalkyl group or a C1-C8 perfluoroalkoxy group, n is 0 or 1, m is an integer from 1 to 3, and p is an integer from 1 to 4.
A curable composition comprising:
- A. a fluoroelastomer comprising copolymerized units of a first monomer, said first monomer being a fluoroolefin selected from the group consisting of vinylidene fluoride and tetrafluoroethylene;
- copolymerized units of a second monomer, different from said first monomer, said second monomer selected from the group consisting of i) fluoroolefins, ii) hydrocarbon olefins, iii) perfluoro(alkyl vinyl)ethers and iv) perfluoro(alkoxy vinyl) ethers;
- and copolymerized units of a fluorinated vinyl ether cure site monomer of the formula CF3CHFCF2—(O)n—(CH2)m—(CF2)p—Rf—OCF═CF2, wherein Rf is a C1-C8 perfluoroalkyl group or a C1-C8 perfluoroalkoxy group, n is 0 or 1, m is an integer from 1 to 3, and p is an integer from 1 to 4;
- B. a polyhydroxy crosslinking agent;
- C. a cure accelerator;
- and
- D. a metal oxide or metal hydroxide.
Dependencies are inferred from the claim text.