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EP0041737B1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process to produce novel fluorocarbon vinyl ethers and resulting polymers

Assignee: Dow Chemical Co
•
Filing: 1981-06-10
•
Granted: 1984-08-29
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Expires: 2001-06-10
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Abstract

Abstract Novel vinyl ethers are prepared in decarboxylation reactions of novel acid fluoride compounds according to the following reaction: <CHEM> wherein a is 0 or an integer greater than 0; b is 0 or an integer greater than 0; n = 1 or an integer greater than 1; Rf and R<1> are independently selected from the group consisting of F, Cl, perfluoroalkyl or fluorochloroalkyl; X = F, Cl, Br or mixtures thereof when n > 1 X min = Cl or Br; Y is an acid group or an acid derivative easily convertible to an acid group; Z = F, Cl, Br, OH, NRR min or OA; R and R min are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atoms, and aryl; and A = alkali metal, quaternary nitrogen, or R. These vinyl ethers may be homopolymerized with themselves or copolymerized with other vinyl ethers.

Inventors

  • 👤 Bobby Ray Ezzell
  • 👤 William Paul Carl
  • 👤 William August Mod

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-06 06:15
CPC Classifications
C; C07; C07C; C07C59/00; C07C59/235; C07C59/305; C07C59/315; C08; C08F; C08F216/00; C08F216/12; C08F216/14; C07C309/00; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/15; C07C43/16; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C08F16/00; C08F16/12; C08F16/14

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 122 words
As a composition of matter, compounds represented by the formula where n = 1 or an integer greater than 1; X = Cl, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 , and C=N where Z' is F, Cl, Br, OH, NRR' or OA, R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, A is an alkali metal, quaternary nitrogen radical, or R; R f and Rf are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0.
Claim 2
Dependent Claim 122 words
As a composition of matter, compounds represented by the formula where n = 1 or an integer greater than 1; X = Cl, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 , and C=N where Z' is F, Cl, Br, OH, NRR' or OA, R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, A is an alkali metal, quaternary nitrogen radical, or R; R f and Rf are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0.
Claim 3
Dependent Claim 29 words
The compounds of Claim 1 wherein a = 0-3; b = 0-3; n = 1 to 6; R f = F or CI and Rf = F or CI.
Claim 4
Dependent Claim 15 words
The compounds of Claim 1 or 2 wherein n = 1 and X = CI.
Claim 5
Independent Claim 169 words
A method of producing the compounds represented by the formula where n = 1 or an integer greater than 1; X = F, Cl, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 , and C≡N where Z' is F, Cl, Br, OH, NRR' or OA, R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, A is an alkali metal, quaternary nitrogen radical, or R; R f and Rf are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0, which comprises decarboxylating compounds of the formula: at a temperature and for a time sufficient to form said compound; wherein X' = Cl or Br; Z is F, Cl, Br, OH, NRR' or OA; and the other meanings are the same as in the end product.
Claim 6
Independent Claim 169 words
A method of producing the compounds represented by the formula where n = 1 or an integer greater than 1; X = F, Cl, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 , and C≡N where Z' is F, Cl, Br, OH, NRR' or OA, R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, A is an alkali metal, quaternary nitrogen radical, or R; R f and Rf are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0, which comprises decarboxylating compounds of the formula: at a temperature and for a time sufficient to form said compound; wherein X' = Cl or Br; Z is F, Cl, Br, OH, NRR' or OA; and the other meanings are the same as in the end product.
Claim 7
Dependent Claim 26 words
The method of Claim 4 wherein a = 0―3; b = 0―3; R f = F or Cl; = F or Cl and n = 1―6.
Claim 8
Dependent Claim 20 words
The method of Claim 4 or 5 wherein n = 1; X' = Cl and Y = Z'SO 2 .
Claim 9
Independent Claim 21 words
The method of any one of Claims 4 to 6 wherein n = 1; X = CI and X' = Cl.
Claim 10
Dependent Claim 22 words
The method of Claim 4 wherein the method is carried out in the presence of Na 2 CO 3 as an activator.
Claim 11
Dependent Claim 199 words
A polymerization method comprising reacting in the presence of an initiator, at least two different types of monomers for a time and a temperature sufficient to cause polymerization: wherein at least one monomer is selected from a first group of compounds represented by the formula where n = 1 or an integer greater than 1; X is Cl, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 , or C=N where Z' is selected from the group consisting of F, Cl, Br, OH, NRR' or OA; where R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, and A is an alkali metal, a quaternary nitrogen radical, or R; R f and are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0; and at least one monomer is selected from a second group of compounds consisting of tetrafluoroethylene, trifluoromonochloroethylene, trifluoroethylene, vinylidine fluoride, 1,1,-difluoro-2,2-dichloroethylene, 1,1-diftuoro-2-chloroethylene, hexafluoropropylene, 1,1,1,3,3-pentafluoropropylene, octafluoroisobutylene, ethylene, vinyl chloride, trifluoronitrosomethane, perfluoronitrosoethane, and alkyl vinyl ethers.
Claim 12
Dependent Claim 199 words
A polymerization method comprising reacting in the presence of an initiator, at least two different types of monomers for a time and a temperature sufficient to cause polymerization: wherein at least one monomer is selected from a first group of compounds represented by the formula where n = 1 or an integer greater than 1; X is Cl, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 , or C=N where Z' is selected from the group consisting of F, Cl, Br, OH, NRR' or OA; where R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, and A is an alkali metal, a quaternary nitrogen radical, or R; R f and are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0; and at least one monomer is selected from a second group of compounds consisting of tetrafluoroethylene, trifluoromonochloroethylene, trifluoroethylene, vinylidine fluoride, 1,1,-difluoro-2,2-dichloroethylene, 1,1-diftuoro-2-chloroethylene, hexafluoropropylene, 1,1,1,3,3-pentafluoropropylene, octafluoroisobutylene, ethylene, vinyl chloride, trifluoronitrosomethane, perfluoronitrosoethane, and alkyl vinyl ethers.
Claim 13
Dependent Claim 26 words
The method of Claim 9 wherein a = 0-3; b = 0-3; n = 1-6; R f = F or CI and Rf= F or Cl.
Claim 14
Dependent Claim 15 words
The method of Claim 9 or 10, wherein n = 1 and X = Cl.
Claim 15
Dependent Claim 119 words
A polymeric composition having pendant groups comprising where n = 1 or an integer greater than 1; X = CI, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 ,. and C-N where Z' is F, Cl, Br, OH, NRR' or OA, R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, A is an alkali metal, quaternary nitrogen radical, or R; R f and Rlf are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0.
Claim 16
Dependent Claim 119 words
A polymeric composition having pendant groups comprising where n = 1 or an integer greater than 1; X = CI, Br or mixtures thereof when n > 1; Y is selected from the group consisting of Z'SO 2 ,. and C-N where Z' is F, Cl, Br, OH, NRR' or OA, R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more carbon atoms and an aryl, A is an alkali metal, quaternary nitrogen radical, or R; R f and Rlf are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoroalkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0.
Claim 17
Dependent Claim 72 words
Use of a compound according to any of Claims 1 to 3 in a polymerization reaction, characterized by reacting at least one of these compounds in the presence of an initiator and at a temperature sufficient to cause polymerization together with at least one monomer selected from the group of compounds consisting of tetrafluoroethylene, trifluoromonochloroethylene, trifluoroethylene, vinylidene fluoride, 1,1-difluoro-2,2-dichloroethylene, 1,1-difluoro-2-chloroethylene, hexafluoropropylene, 1,1,1,3,3-pentafluoropropylene, octafluoroisobutylene, ethylene, vinyl chloride, trifluoronitrosomethane, perfluoronitrosoethane, and alkyl vinyl ethers.

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