US5198513A
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US
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Reactive compounds containing perfluorovinyl groups
Assignee: Dow Chemical Co
•
Filing: 1991-03-12
•
Granted: 1993-03-30
•
Expires: 2011-03-12
Abstract
Abstract A compound having at least one perfluorovinyl group and at least one functional group is suitable for reacting with and/or forming polymers. The compound is preferably of Formula I: (G)n-R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF═CF 2 ) groups; and G represents any reactive functional group or a group convertible into a reactive functional groups. A process for preparing a compound of Formula I comprises the steps of: (a) preparing a 2-halotetrafluoro compound of the Formula III: (Q--CF.sub.2 --CF.sub.2 -X).sub.m -R-(G").sub.n wherein R, X, m and n are as described for Formula I and Q is bromine, chlorine or iodine; and G" is a functional group, or a functional group suitable for conversion into G; (b) chemically modifying group G" to produce functional group G; and (c) dehalogenating the 2-halotetrafluoro compound to form the corresponding trifluorovinyl compound.
Inventors
- 👤 Katherine S. Clement
- 👤 David A. Babb
- 👤 Bobby R. Ezzell
- 👤 W. Frank Richey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:59
CPC Classifications
C; C07; C07C; C07C47/00; C07C47/52; C07C47/575; C07C205/00; C07C205/27; C07C205/35; C07C205/36; C07C205/37; C07C217/00; C07C217/78; C07C217/80; C07C217/82; C07C217/84; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C07C45/00; C07C45/61; C07C45/65; C07C45/67; C07C45/68; C07C45/70; C07C45/72; C07C49/00; C07C49/76; C07C49/84; C07C65/00; C07C65/21; C07C69/00; C07C69/017; C07C69/76; C07C69/84; C07C69/92; C08; C08G; C08G64/00; C08G64/04; C08G64/06; C08G64/08; C08G64/10; C08G64/14
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
85 words
A reaction product of a compound having a structure represented by Formula I: (G).sub.n -R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of --(XCF═CF 2 ) groups, and G represents any reactive functional group or a group convertible into a reactive functional group and a polymer wherein the reaction between the compound and the polymer takes place at G on the compound.
Claim 2
Dependent Claim
85 words
A reaction product of a compound having a structure represented by Formula I: (G).sub.n -R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of --(XCF═CF 2 ) groups, and G represents any reactive functional group or a group convertible into a reactive functional group and a polymer wherein the reaction between the compound and the polymer takes place at G on the compound.
Claim 3
Dependent Claim
12 words
The reaction product of claim 1 wherein the polymer is an oligomer.
Claim 4
Dependent Claim
97 words
A reaction product of a compound having a structure represented by Formula I: (G).sub.n -R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is a number of --(XCF═CF 2 ) groups, and G represents any reactive functional group or a group convertible into a reactive functional group and a di- or polyfunctional compound wherein the reaction between the compound of Formula I and the di- or polyfunctional compound takes place at G on the compound of Formula I.
Claim 5
Dependent Claim
97 words
A reaction product of a compound having a structure represented by Formula I: (G).sub.n -R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is a number of --(XCF═CF 2 ) groups, and G represents any reactive functional group or a group convertible into a reactive functional group and a di- or polyfunctional compound wherein the reaction between the compound of Formula I and the di- or polyfunctional compound takes place at G on the compound of Formula I.
Claim 6
Dependent Claim
92 words
The reaction product of claim 1 wherein R is an aromatic or aliphatic group which is unsubstituted or inertly substituted; and X is independently an oxygen atom, a sulfur atom, a carboxylic or thiocarboxylic ester group, a sulfone, a sulfoxide, perfluoroalkylene, perfluoroalkylene ether, alkylene, acetylene, a phosphine, a carbonyl or thio carbonyl group; seleno; telluro; nitrido; a silanediyl, trisilanediyl tetrasilanetetrayl, siloxanediyl, disiloxanediyl, trisiloxyl, trisilazanyl, or silythio group; a boranediyl or methylboranediyl group; or a combination thereof; R is an aromatic group; and wherein m and n are each independently 1 or 2.
Claim 7
Dependent Claim
12 words
The reaction product of claim 4 wherein the polymer is an oligomer.
Claim 8
Dependent Claim
92 words
The reaction product of claim 3 wherein R is an aromatic or aliphatic group which is unsubstituted or inertly substituted; and X is independently an oxygen atom, a sulfur atom, a carboxylic or thiocarboxylic ester group, a sulfone, a sulfoxide, perfluoroalkylene, perfluoroalkylene ether, alkylene, acetylene, a phosphine, a carbonyl or thio carbonyl group; seleno; telluro; nitrido; a silanediyl, trisilanediyl tetrasilanetetrayl, siloxanediyl, disiloxanediyl, trisiloxyl, trisilazanyl, or silylthio group a boranediyl or methylboranediyl group; or a combination thereof; R is an aromatic group; and wherein m and n are each independently 1 or 2.
Claim 9
Dependent Claim
133 words
A process for preparing a compound of Formula I: (G.sub.n)-R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF═CF 2 ) groups; and G represents any reactive functional group or a group convertible into a reactive functional groups comprising steps of: (a) preparing a 2-halotetrafluoro compound of the Formula III: (Q--CF.sub.2 --CF.sub.2 -X)m-R(G").sub.n wherein X, G, m and n are as defined for Formula I and Q is bromine, chlorine or iodine: and G" is a functional group G, or a functional group suitable for conversion into G; (b) chemically modifying group G" to produce functional group G; and (c) dehalogenating the 2-halotetrafluoro compound to form the corresponding trifluorovinyl compound.
Claim 10
Dependent Claim
133 words
A process for preparing a compound of Formula I: (G.sub.n)-R-(X--CF═CF.sub.2).sub.m wherein R represents an optionally substituted hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of (XCF═CF 2 ) groups; and G represents any reactive functional group or a group convertible into a reactive functional groups comprising steps of: (a) preparing a 2-halotetrafluoro compound of the Formula III: (Q--CF.sub.2 --CF.sub.2 -X)m-R(G").sub.n wherein X, G, m and n are as defined for Formula I and Q is bromine, chlorine or iodine: and G" is a functional group G, or a functional group suitable for conversion into G; (b) chemically modifying group G" to produce functional group G; and (c) dehalogenating the 2-halotetrafluoro compound to form the corresponding trifluorovinyl compound.
Claim 11
Dependent Claim
54 words
The process of claim 7 wherein step (a) comprises the steps of: (1) forming a salt having an anion represented by Formula IV: -X-R-G' (2) reacting the salt with a 1,2-dihalo-1,1,2,2-tetrafluoroethane having as the halo groups, halogens which are bromine, iodine or chlorine or mixtures thereof, which halo groups include at least one bromine.
Claim 12
Dependent Claim
12 words
The reaction product of claim 1 wherein R is an aromatic group.
Claim 13
Dependent Claim
59 words
The reaction product of claim 9 wherein X is independently an oxygen atom, a sulfur atom, a carboxylic or thiocarboxylic ester group, a sulfone, a sulfoxide, alkylene, acetylene, a phosphine, a carbonyl or thio carbonyl group; seleno; telluro; nitrido; a silanediyl, trisilanediyl tetrasilanetetrayl, siloxanediyl, disiloxanediyl, trisiloxyl, trisilazanyl, or silythio group; a boranediyl or methylboranediyl group; or a combination thereof.
Claim 14
Dependent Claim
17 words
The reaction product of claim 9 wherein X is bonded to an aromatic carbon atom of R.
Claim 15
Dependent Claim
17 words
The reaction product of claim 11 wherein R has from about 6 to about 25 carbon atoms.
Claim 16
Dependent Claim
14 words
The reaction product of claim 12 wherein X is oxygen, sulfur, sulfoxide or sulfone.
Claim 17
Dependent Claim
35 words
The reaction product of claim 13 wherein G is selected from hydroxyl, carboxylic or thiocarboxylic acid ester groups, carboxylic acid groups, acyl chlorides, alkyl groups when R is aromatic, isocyanates and primary or secondary amines.
Claim 18
Dependent Claim
19 words
The reaction product of claim 9 wherein R has a molecular weight of from about 14 to about 20,000.
Claim 19
Dependent Claim
12 words
The reaction product of claim 3 wherein R is an aromatic group.
Claim 20
Dependent Claim
78 words
The reaction product claim 9 wherein G is selected from hydroxyl groups (both alcoholic and phenolic), carboxylic acid groups, acyl halides, isocyanates, acyl azides, acetyl groups, primary or secondary amines, sulfide groups, sulfonic acid groups, sulfonamide groups, ketones, aldehydes, epoxy groups, primary or secondary amides; alkyl groups when R is aromatic, vinyl, allyl, acetylene groups, halo groups, nitro groups, cyano groups, anhydrides, imides, cyanate groups, trihalomethyl, alkyl or alkoxy when R is aromatic, carboxylic or thiocarboxylic acid esters.
Claim 21
Dependent Claim
12 words
The reaction product of claim 17 wherein the polymer is an oligomer.
Claim 22
Dependent Claim
78 words
The reaction product claim 16 wherein G is selected from hydroxyl groups (both alcoholic and phenolic), carboxylic acid groups, acyl halides, isocyanates, acyl azides, acetyl groups, primary or secondary amines, sulfide groups, sulfonic acid groups, sulfonamide groups, ketones, aldehydes, epoxy groups, primary or secondary amides; alkyl groups when R is aromatic, vinyl, allyl, acetylene groups, halo groups, nitro groups, cyano groups, anhydrides, imides, cyanate groups, trihalomethyl, alkyl or alkoxy when R is aromatic, carboxylic or thiocarboxylic acid esters.
Claim 23
Dependent Claim
59 words
The reaction product of claim 16 wherein X is independently an oxygen atom, a sulfur atom, a carboxylic or thiocarboxylic ester group, a sulfone, a sulfoxide, alkylene, acetylene, a phosphine, a carbonyl or thio carbonyl group; seleno; telluro; nitrido; a silanediyl, trisilanediyl tetrasilanetetrayl, siloxanediyl, disiloxanediyl, trisiloxyl, trisilazanyl, or silylthio group; a boranediyl or methylboranediyl group; or a combination thereof.
Claim 24
Dependent Claim
17 words
The reaction product of claim 16 wherein X is bonded to an aromatic carbon atom of R.
Claim 25
Dependent Claim
17 words
The reaction product of claim 21 wherein R has from about 6 to about 25 carbon atoms.
Claim 26
Dependent Claim
14 words
The reaction product of claim 22 wherein X is oxygen, sulfur, sulfoxide or sulfone.
Claim 27
Dependent Claim
35 words
The reaction product of claim 23 wherein G is selected from hydroxyl, carboxylic or thiocarboxylic acid ester groups, carboxylic acid groups, acyl chlorides, alkyl groups when R is aromatic, isocyanates and primary or secondary amines.
Claim 28
Dependent Claim
19 words
The reaction product of claim 16 wherein R has a molecular weight of from about 14 to about 20,000.
Claim 29
Dependent Claim
70 words
The reaction product of claim 1 wherein G is selected from phenolic --OH, acyl halides, isocyanates, acyl azides, acetyl groups, primary or secondary amines, sulfide groups, sulfonic acid groups, sulfonamide groups, ketones, aldehydes, primary or secondary amides; alkyl groups when R is aromatic, vinyl, allyl, acetylene groups, halo groups, nitro groups, cyano groups, anhydrides, imides, cyanate groups, trihalomethyl, alkyl or alkoxy when R is aromatic, carboxylic or thiocarboxylic acid esters.
Claim 30
Dependent Claim
70 words
The reaction product of claim 3 wherein G is selected from phenolic --OH, acyl halides, isocyanates, acyl azides, acetyl groups, primary or secondary amines, sulfide groups, sulfonic acid groups, sulfonamide groups, ketones, aldehydes, primary or secondary amides; alkyl groups when R is aromatic, vinyl, allyl, acetylene groups, halo groups, nitro groups, cyano groups, anhydrides, imides, cyanate groups, trihalomethyl, alkyl or alkoxy when R is aromatic, carboxylic or thiocarboxylic acid esters.
Claim 31
Dependent Claim
58 words
The reaction product of claim 1 wherein R represents an optionally substituted aromatic hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of --(XCF═CF 2 ) groups, and G represents at least one phenolic hydroxyl group, acyl halide, carboxylic acid or amine group.
Claim 32
Dependent Claim
58 words
The reaction product of claim 3 wherein R represents an optionally substituted aromatic hydrocarbyl group, X represents any group which links R and a perfluorovinyl group; n is the number of G groups, m is the number of --(XCF═CF 2 ) groups, and G represents at least one phenolic hydroxyl group, acyl halide, carboxylic acid or amine group.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-03-29 | 1996-09-28 | 1997-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-03-29 | 2000-09-28 | 2001-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-03-29 | 2004-09-28 | 2005-03-30 | $7700.00 | Window Closed / Lapsed |