US5912286A
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Silicone-containing fluoropolymers for controlled release of organic leachants
Assignee: NAVY United States, AS REPRESENDTED BY SECRETARY OF
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Filing: 1997-08-29
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Granted: 1999-06-15
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Expires: 2017-08-29
Abstract
Abstract A composition comprises a leachable organic compound distributed throughout a polymer matrix formed by reacting a fluoroepoxy compound of the formula: ##STR1## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR2## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater. The leaching rate of the leachable organic compound is controlled by selecting the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent. The composition may be used as a coating for protecting underwater substrates from fouling by marine organisms.
Inventors
- 👤 James R. Griffith
- 👤 Stephen L. Snyder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 02:07
CPC Classifications
C; C09; C09D; C09D5/00; C09D5/16; C09D5/1656; C09D5/1662; A; A01; A01N; A01N25/00; A01N25/24; A01N43/00; A01N43/72; A01N43/80; C08; C08G; C08G59/00; C08G59/18; C08G59/20; C08G59/22; C08G59/30; C08G59/40; C08G59/50; C08G59/504; C09D5/1606; C09D5/1612; C09D5/1625
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
72 words
A composition comprising a polymer matrix and a leachable organic compound distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR7## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR8## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater.
Claim 2
Dependent Claim
72 words
A composition comprising a polymer matrix and a leachable organic compound distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR7## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR8## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater.
Claim 3
Dependent Claim
22 words
The composition of claim 1, wherein the leachable organic compound comprises from about 0.5 to about 25% by weight of the composition.
Claim 4
Dependent Claim
22 words
The composition of claim 1, wherein the leachable organic compound comprises from about 1 to about 20% by weight of the composition.
Claim 5
Dependent Claim
13 words
The composition of claim 1, wherein the leachable organic compound is a biocide.
Claim 6
Dependent Claim
14 words
The composition of claim 1, wherein the leachable organic compound is a 3-isothiazolone compound.
Claim 7
Dependent Claim
33 words
The composition of claim 1, wherein the leachable organic compound is selected from the group consisting of 4,5-dichloro-2-cyclohexyl-3-isothiazolone, 4,5-dichloro-2-n-hexyl-3-isothiazolone, 4,5-dichloro-2-n-octyl-3-isothiazolone, 4,5-dichloro-2-n-vinyl-3-isothiazolone, 4,5-dichloro-2-(4'-chlorobenzyl)-3-isothiazolone, 4-methyl-5-chloro-2-(4'-chlorophenyl)-3-isothiazolone, 5-chloro-2-(4'-chlorobenzyl)-3-isothiazolone, 5-chloro- 2-(2'-phenylethyl)- 3-isothiazolone, 4,5-dichloro-2-(2'-phenylethyl)-3-isothiozolone, 4-methyl-5-chloro-2-(3', 4'-diethylbenzyl)-3-isothiazolone, and mixtures thereof.
Claim 8
Dependent Claim
12 words
The composition of claim 1, wherein the leachable organic compound is 4,5-dichloro-2-n-octyl-3-isothiazolone.
Claim 9
Independent Claim
168 words
A method of making a composition comprising a polymer matrix and a leachable organic compound distributed throughout the polymer matrix, the composition having the property that when the composition is placed in a liquid medium, the leachable organic compound leaches from the polymer matrix at a predetermined selectable rate, the method comprising the steps of, combining a leachable organic compound with a fluoroepoxy compound of the formula: ##STR9## wherein x is an integer from 0 to 12, and a silicone amine curing agent of the formula: ##STR10## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater, allowing the fluoroepoxy compound to react with the silicone amine curing agent to form a polymer matrix having the leachable organic compound distributed throughout the polymer matrix, wherein the predetermined selectable rate of leaching of the leachable organic compound is controlled by selecting the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent.
Claim 10
Independent Claim
168 words
A method of making a composition comprising a polymer matrix and a leachable organic compound distributed throughout the polymer matrix, the composition having the property that when the composition is placed in a liquid medium, the leachable organic compound leaches from the polymer matrix at a predetermined selectable rate, the method comprising the steps of, combining a leachable organic compound with a fluoroepoxy compound of the formula: ##STR9## wherein x is an integer from 0 to 12, and a silicone amine curing agent of the formula: ##STR10## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater, allowing the fluoroepoxy compound to react with the silicone amine curing agent to form a polymer matrix having the leachable organic compound distributed throughout the polymer matrix, wherein the predetermined selectable rate of leaching of the leachable organic compound is controlled by selecting the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent.
Claim 11
Dependent Claim
142 words
A coating composition for protecting a substrate in an underwater medium from fouling by organisms comprising a polymer matrix and a leachable biocide distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR11## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR12## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater, wherein the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent are selected to provide a polymer matrix that allows an effective amount of the leachable biocide for protecting a substrate in an underwater medium from fouling by organisms to leach from the polymer matrix into the underwater medium.
Claim 12
Dependent Claim
142 words
A coating composition for protecting a substrate in an underwater medium from fouling by organisms comprising a polymer matrix and a leachable biocide distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR11## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR12## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater, wherein the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent are selected to provide a polymer matrix that allows an effective amount of the leachable biocide for protecting a substrate in an underwater medium from fouling by organisms to leach from the polymer matrix into the underwater medium.
Claim 13
Dependent Claim
21 words
The composition of claim 9 wherein the leachable biocide comprises from about 0.5 to about 25% by weight of the composition.
Claim 14
Dependent Claim
21 words
The composition of claim 9 wherein the leachable biocide comprises from about 1 to about 20% by weight of the composition.
Claim 15
Dependent Claim
13 words
The composition of claim 9 wherein the leachable biocide is a 3-isothiazolone compound.
Claim 16
Dependent Claim
31 words
The composition of claim 9 wherein the leachable biocide is selected from the group consisting of 4,5-dichloro-2-cyclohexyl-3-isothiazolone, 4,5-dichloro-2-n-hexyl-3-isothiazolone, 4,5-dichloro-2-n-octyl-3-isothiazolone, 4,5-dichloro-2-n-vinyl-3-isothiazolone, 4,5-dichloro-2-(4'-chlorobenzyl)-3-isothiazolone, 4-methyl-5-chloro-2-(4'-chlorophenyl)-3-isothiazolone, 5-chloro-2-(4'-chlorobenzyl)-3-isothiazolone, 5-chloro-2-(2'-phenylethyl)-3-isothiazolone, 4,5-dichloro-2-(2 '-phenylethyl)-3-isothiozolone, 4-methyl-5-chloro-2-(3', 4'-diethylbenzyl)-3-isothiazolone, and mixtures thereof.
Claim 17
Dependent Claim
11 words
The composition of claim 9 wherein the leachable biocide is 4,5-dichloro-2-n-octyl-3-isothiazolone.
Claim 18
Dependent Claim
97 words
A coating composition for protecting a substrate in an underwater medium from fouling by organisms comprising a polymer matrix and a leachable biocide distributed throughout the polymer matrix, wherein the leachable biocide is 4,5-dichloro-2-n-octyl-3-isothiazolone and comprises about 1 to about 20% of the coating composition by weight, and the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR13## wherein x is 7, with a silicone amine curing agent of the formula: ##STR14## where n is the average degree of polymerization of the silicone amine curing agent and is about 11.
Claim 19
Dependent Claim
97 words
A coating composition for protecting a substrate in an underwater medium from fouling by organisms comprising a polymer matrix and a leachable biocide distributed throughout the polymer matrix, wherein the leachable biocide is 4,5-dichloro-2-n-octyl-3-isothiazolone and comprises about 1 to about 20% of the coating composition by weight, and the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR13## wherein x is 7, with a silicone amine curing agent of the formula: ##STR14## where n is the average degree of polymerization of the silicone amine curing agent and is about 11.
Claim 20
Dependent Claim
86 words
An article comprising a substrate and a coating composition disposed on the substrate, the coating composition comprising a polymer matrix and a leachable organic compound distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR15## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR16## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater.
Claim 21
Dependent Claim
86 words
An article comprising a substrate and a coating composition disposed on the substrate, the coating composition comprising a polymer matrix and a leachable organic compound distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR15## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR16## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater.
Claim 22
Independent Claim
155 words
A method of protecting a substrate in an underwater medium from fouling by organisms comprising the step of forming on the surface of the substrate a coating composition comprising a polymer matrix and a leachable biocide distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR17## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR18## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater, wherein the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent are selected to provide a polymer matrix that allows an effective amount of the leachable biocide for protecting a substrate in an underwater medium from fouling by organisms to leach from the polymer matrix into the underwater medium.
Claim 23
Independent Claim
155 words
A method of protecting a substrate in an underwater medium from fouling by organisms comprising the step of forming on the surface of the substrate a coating composition comprising a polymer matrix and a leachable biocide distributed throughout the polymer matrix, wherein the polymer matrix comprises the reaction product formed by reacting a fluoroepoxy compound of the formula: ##STR17## wherein x is an integer from 0 to 12, with a silicone amine curing agent of the formula: ##STR18## where n is the average degree of polymerization of the silicone amine curing agent and is 1 or greater, wherein the value of x in the fluoroepoxy compound and the value of n in the silicone amine curing agent are selected to provide a polymer matrix that allows an effective amount of the leachable biocide for protecting a substrate in an underwater medium from fouling by organisms to leach from the polymer matrix into the underwater medium.
Claim 24
Dependent Claim
21 words
The method of claim 17 wherein the leachable biocide comprises from about 0.5 to about 25% by weight of the composition.
Claim 25
Dependent Claim
21 words
The method of claim 17 wherein the leachable biocide comprises from about 1 to about 25% by weight of the composition.
Claim 26
Dependent Claim
13 words
The method of claim 17 wherein the leachable biocide is a 3-isothiazolone compound.
Claim 27
Dependent Claim
32 words
The method of claim 17 wherein the leachable biocide is selected from the group consisting of 4,5-dichloro-2-cyclohexyl-3-isothiazolone, 4,5-dichloro-2-n-hexyl-3-isothiazolone, 4,5-dichloro-2-n-octyl-3-isothiazolone, 4,5-dichloro-2-n-vinyl-3-isothiazolone, 4,5-dichloro-2-(4'-chlorobenzyl)-3 -isothiazolone, 4-methyl-5-chloro-2-(4'-chlorophenyl)-3-isothiazolone, 5-chloro-2-(4'- chlorobenzyl)-3-isothiazolone, 5-chloro-2-(2'-phenylethyl)-3-isothiazolone, 4,5-dichloro-2-(2'-phenylethyl)-3-isothiozolone, 4-methyl-5-chloro-2-(3', 4'-diethylbenzyl)-3-isothiazolone, and mixtures thereof.
Claim 28
Dependent Claim
11 words
The method of claim 17 wherein the leachable biocide is 4,5-dichloro-2-n-octyl-3-isothiazolone.
References Cited (Backward Citations)
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