US5162468A
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Perfluorovinyl compounds
Assignee: Dow Chemical Co
•
Filing: 1991-03-12
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Granted: 1992-11-10
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Expires: 2011-03-12
Abstract
Abstract Compounds have a structure represented by Formula I: CF.sub.2 ═CF--X--R--(X--CF═CF.sub.2).sub.m wherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF═CF 2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of: (a) forming a salt having anion corresponding to a compound of Formula II: HX--R--(XH.sub.m); wherein X, R and m are as defined for Formula I: (b) reacting the salt with a 1,2-dihalo-1,1,2,2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III: Z--CF.sub.2 CF.sub.2 --X--R--(X--CF.sub.2 CF.sub.2 --Z).sub.m wherein X, R and m are as defined for Formula I and each Z is independently iodine or bromine; (c) eliminating the halogen atoms represented by Z to form the perfluorovinyl compound represented by Formula I.
Inventors
- 👤 David A. Babb
- 👤 Katherine S. Clement
- 👤 Bobby R. Ezzell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:16
CPC Classifications
C; C07; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/17; C07C22/00; C07C22/02; C07C22/04; C07C22/08; C07C43/20; C07C43/225; C07C65/00; C07C65/21; C07C69/00; C07C69/76; C07C69/84; C07C69/92; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/18
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
63 words
A polymer prepared by thermally forming perfluorocyclobutane rings from compounds having a structure represented by Formula I: CF.sub.2 ═CF--X--R--(X--CF═CF.sub.2).sub.m wherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF═CF 2 ; and m is an integer of from 1 to about 3.
Claim 2
Dependent Claim
63 words
A polymer prepared by thermally forming perfluorocyclobutane rings from compounds having a structure represented by Formula I: CF.sub.2 ═CF--X--R--(X--CF═CF.sub.2).sub.m wherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF═CF 2 ; and m is an integer of from 1 to about 3.
Claim 3
Dependent Claim
57 words
The polymer of claim 1 prepared by thermally forming perfluorocyclobutane rings from a compound of Formula I wherein X is selected from the group consisting of an oxygen atom, carboxylic and thiocarboxylic ester groups, phosphines, carbonyl and thio carbonyl groups; seleno; telluro; nitrido; silanediyl, trisilanediyl tetrasilanetetrayl, siloxanediyl, disiloxanediyl, trisiloxyl, trisilazanyl, or silylthio groups; boranediyl or methylboranediyl groups.
Claim 4
Dependent Claim
37 words
The polymer of claim 1 prepared by thermally forming perfluorocyclobutane rings from a compound of Formula I wherein X is selected from the group consisting of oxygen atoms, sulfur atoms, sulfoxide, sulfone, carbonyl, thiocarbonyl and silanediyl groups.
Claim 5
Dependent Claim
22 words
The polymer if claim 3 prepared by thermally forming perfluorocyclobutane rings from a compound of Formula I wherein the X's are oxygen.
Claim 6
Dependent Claim
46 words
The polymer of claim 1 prepared by thermally forming perfluorocyclobutane rings from a compound of Formula I wherein each X is independently an oxygen atom, a sulfur atom, a sulfoxide group, or a sulfone group; and wherein R is an unsubstituted or inertly substituted aromatic group.
Claim 7
Dependent Claim
41 words
The polymer of claim 5 prepared by thermally forming perfluorocyclobutane rings from a compound of Formula I wherein the aromatic group is selected from the group consisting of biphenylene; phenylene; 9,9'-diphenylfluorene, oxydiphenylene; thiodiphenylene; 2,2-diphenylene propane; 2,2-diphenylene, 1,1,1,3,3,3-hexafluoropropane; 1,1-diphenylene-1-phenylethane; naphthalene; and anthracene.
Claim 8
Independent Claim
151 words
A method of preparing compounds of Formula I: CF.sub.2 ═CF--X--R--(X--CF═CF.sub.2).sub.m wherein each X is independently --O--, --S--, --SO-- or --SO 2 --; m is from 1 to about 3; and R is a hydrocarbyl group which group is substituted or inertly substituted, by a process comprising the steps of: (a) forming a salt having anion corresponding to a compound of Formula II: HX--R--(XH).sub.m ; wherein X, R and m are as defined for Formula I; (b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III: Z--CF.sub.2 CF.sub. --X--R--(X--CF.sub.2 CF.sub.2 --Z).sub.m wherein X, R and m are as defined for Formula I and each Z is independently iodine or bromine; (c) eliminating the halogen atoms represented by Z to form the perfluorovinyl compound represented by Formula I.
Claim 9
Independent Claim
151 words
A method of preparing compounds of Formula I: CF.sub.2 ═CF--X--R--(X--CF═CF.sub.2).sub.m wherein each X is independently --O--, --S--, --SO-- or --SO 2 --; m is from 1 to about 3; and R is a hydrocarbyl group which group is substituted or inertly substituted, by a process comprising the steps of: (a) forming a salt having anion corresponding to a compound of Formula II: HX--R--(XH).sub.m ; wherein X, R and m are as defined for Formula I; (b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III: Z--CF.sub.2 CF.sub. --X--R--(X--CF.sub.2 CF.sub.2 --Z).sub.m wherein X, R and m are as defined for Formula I and each Z is independently iodine or bromine; (c) eliminating the halogen atoms represented by Z to form the perfluorovinyl compound represented by Formula I.
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