US4804727A
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US
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Process to produce novel fluorocarbon vinyl ethers and resulting polymers
Assignee: Dow Chemical Co
•
Filing: 1987-05-05
•
Granted: 1989-02-14
•
Expires: 2007-05-05
Abstract
Abstract Novel vinyl ethers are prepared in decarboxylation reactions of novel acid fluoride compounds according to the following reaction: ##STR1## 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; R f and R f ' are independently selected from the group consisting of F, Cl, perfluoroalkyl or fluorochloroalkyl; X=F, Cl, Br or mixtures thereof when n>1 X'=Cl or Br; D is an acid group or an acid derivative easily convertible to an acid group; Z=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 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 R. Ezzell
- 👤 William P. Carl
- 👤 William A. Mod
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 02:01
CPC Classifications
C; C08; C08F; C08F216/00; C08F216/12; C08F216/14; C07; C07C; C07C309/00; 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: 34
Claim 1
Independent Claim
147 words
A polymerization method which comprises reacting, in the presence of an initiator, one or more compounds of the general formula ##STR38## for a time and at a temperature sufficient to cause polymerization; wherein n=one to six; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR39## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoro alkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0.
Claim 2
Dependent Claim
147 words
A polymerization method which comprises reacting, in the presence of an initiator, one or more compounds of the general formula ##STR38## for a time and at a temperature sufficient to cause polymerization; wherein n=one to six; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR39## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' are independently selected from the group consisting of F, Cl, a perfluoroalkyl radical and a chlorofluoro alkyl radical; a=0 or an integer greater than 0; b=0 or an integer greater than 0.
Claim 3
Dependent Claim
11 words
The method of claim 1 where D is ZSO 2 .
Claim 4
Dependent Claim
9 words
The method of claim 2 where Z is F.
Claim 5
Dependent Claim
7 words
The method of claim 1 where D=COZ.
Claim 6
Dependent Claim
20 words
The method of claim 1 where a=0-3; b=0-3; n=1-6; R f =F or Cl and R f '=F or Cl.
Claim 7
Dependent Claim
9 words
The method of claim 1 where n=1 and x=Cl.
Claim 8
Dependent Claim
7 words
The method of claim 2 where X=Cl.
Claim 9
Dependent Claim
7 words
The method of claim 2 where n=1.
Claim 10
Dependent Claim
9 words
The product produced by the method of claim 1.
Claim 11
Dependent Claim
197 words
A polymerization method comprising reacting in the presence of an initiator, at least two different types of monomers for a time and at a temperature sufficient to cause polymerization: wherein at least one monomer is selected from a first group of compounds represented by the formula ##STR40## where n=1 to 6; X is Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR41## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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, 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.
Claim 12
Dependent Claim
197 words
A polymerization method comprising reacting in the presence of an initiator, at least two different types of monomers for a time and at a temperature sufficient to cause polymerization: wherein at least one monomer is selected from a first group of compounds represented by the formula ##STR40## where n=1 to 6; X is Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR41## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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, 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.
Claim 13
Dependent Claim
25 words
The method of claim 10 where only one monomer is selected from the first group and only one monomer is selected from the second group.
Claim 14
Dependent Claim
19 words
The method of claim 10 where the monomer(s) selected from the second group is tetrafluoroethylene, chlorotrifluoroethylene or mixtures thereof.
Claim 15
Dependent Claim
11 words
The method of claim 12 where D is ZSO 2 .
Claim 16
Dependent Claim
7 words
The method of claim 12 where D=COZ.
Claim 17
Dependent Claim
20 words
The method of claim 10 where a=0-3; b=0-3; n=1-6; R f =F or Cl and R f '=F or Cl.
Claim 18
Dependent Claim
11 words
The method of claim 10 or 12 where n=1 and X=Cl.
Claim 19
Dependent Claim
9 words
The method of claim 13 where n=1 and X=Cl.
Claim 20
Dependent Claim
9 words
The product produced by the method of claim 16.
Claim 21
Dependent Claim
9 words
The product produced by the method of claim 10.
Claim 22
Dependent Claim
135 words
As a composition of matter, polymers formed by the polymerization of one or more compounds represented by the general formula ##STR42## wherein n=1 to 6; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR43## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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 23
Dependent Claim
135 words
As a composition of matter, polymers formed by the polymerization of one or more compounds represented by the general formula ##STR42## wherein n=1 to 6; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR43## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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 24
Dependent Claim
125 words
As a composition of matter, polymers having pendant groups comprising ##STR44## where n=1 to 6; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR45## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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 25
Dependent Claim
125 words
As a composition of matter, polymers having pendant groups comprising ##STR44## where n=1 to 6; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR45## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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 26
Dependent Claim
178 words
As a composition of matter, polymers formed by the polymerization of at least two different types of monomers, wherein at least one monomer is represented by the general formula ##STR46## wherein n=1 to 6; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR47## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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, 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.
Claim 27
Dependent Claim
178 words
As a composition of matter, polymers formed by the polymerization of at least two different types of monomers, wherein at least one monomer is represented by the general formula ##STR46## wherein n=1 to 6; X=Cl, Br or mixtures thereof when n>1; D is selected from the group consisting of ZSO 2 , ##STR47## or C.tbd.N, where Z is selected from the group consisting of F, Cl, Br, OH, NRR', and 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 R f ' 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, 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.
Claim 28
Dependent Claim
9 words
The polymers of claim 22 where D=ZSO 2 .
Claim 29
Dependent Claim
7 words
The polymers of claim 4 where Z=F.
Claim 30
Dependent Claim
21 words
The polymers of claim 2 where the monomer(s) selected from the second group of compounds is tetrafluoroethylene, chlorotrifluoroethylene or mixtures thereof.
Claim 31
Dependent Claim
7 words
The polymers of claim 22 where D=COZ.
Claim 32
Dependent Claim
23 words
The polymers of claims 20, 21 or 22 where a=0-3; b=0-3; n=1-6; R f =F or Cl and R f '=F or Cl.
Claim 33
Dependent Claim
20 words
The polymers of claim 6 where a=0-3; b=0-3; n=1-6; R f =F or Cl and R f '=F or Cl.
Claim 34
Dependent Claim
16 words
As a composition of matter of any one of claims 20, 21, or 22, where n=1.
References Cited (Backward Citations)
US3114778A
Cited
US2393967A
Cited
US2559752A
Cited
US2593583A
Cited
US3041317A
Cited
US3242218A
Cited
US3214478A
Cited
FR1341087A
Cited
US3250806A
Cited
US3450684A
Cited
US3301893A
Cited
FR1410444A
Cited
DE1238458B
Cited
FR1422147A
Cited
US3282875A
Cited
US3351619A
Cited
US3536733A
Cited
US3560568A
Cited
US3784399A
Cited
GB1406673A
Cited
US4025405A
Cited
US4192725A
Cited
US4035255A
Cited
US4035254A
Cited
US4085071A
Cited
US3969285A
Cited
GB1497748A
Cited
GB1497749A
Cited
US3909378A
Cited
US4151053A
Cited
GB1518387A
Cited
US4065366A
Cited
US4065366B1
Cited
US4126588A
Cited
JPS52118597A
Cited
GB1550874A
Cited
US4153804A
Cited
US4138426A
Cited
US4197179A
Cited
GB2029827A
Cited
US4209635A
Cited
US4337137A
Cited
US4470889A
Cited
US4358412A
Cited
US4358545A
Cited
US4417969A
Cited
US4330654A
Cited
US4462877A
Cited
US4337211A
Cited
US4478695A
Cited
US4687821A
Cited
US4515989A
Cited
US4578512A
Cited
US4554112A
Cited
US4487903A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-02-14 | 1992-08-15 | 1993-02-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-02-14 | 1996-08-15 | 1997-02-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-02-14 | 2000-08-15 | 2001-02-14 | $7700.00 | Window Closed / Lapsed |