US5075378A
Expired / Lapsed
US
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Coating of an epoxy resin, fluorocarbon polymer fluorinated curing agent
Assignee: Standard Oil Co
•
Filing: 1987-06-24
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Granted: 1991-12-24
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Expires: 2007-06-24
Abstract
Abstract A multifunctional coating composition comprising a fluorocarbon polymer, an epoxy resin and a fluorinated curing agent resulting in a fluorinated epoxy resin network with improved properties of corrosion resistance and hydrophobicity.
Inventors
- 👤 Richard C. Smierciak
- 👤 Paul J. Giordano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 03:47
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C09; C09D; C09D163/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
195 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids, and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent selected from the group consisting 4-aminobenzotrifluoride, 4,4'-diaminooctafluorobiphenyl, 3-5-Bis(trifluoromethyl)aniline, 2,2,3,3,4,4-hexafluoro-1,5-pentanediol, decafluoropropionic anhydride, heptaflluorobutyric anhydride, tetrafluororesorcinol, 4,4'-dihydroxyoctafluoro biphenyl and mixtures thereof which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 2
Dependent Claim
195 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids, and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent selected from the group consisting 4-aminobenzotrifluoride, 4,4'-diaminooctafluorobiphenyl, 3-5-Bis(trifluoromethyl)aniline, 2,2,3,3,4,4-hexafluoro-1,5-pentanediol, decafluoropropionic anhydride, heptaflluorobutyric anhydride, tetrafluororesorcinol, 4,4'-dihydroxyoctafluoro biphenyl and mixtures thereof which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 3
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 4-aminobenzotrifluoride which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 4
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 4-aminobenzotrifluoride which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 5
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 4,4'-diaminooctafluorobiphenyl which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 6
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 4,4'-diaminooctafluorobiphenyl which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 7
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of bis(trifluoromethyl)aniline which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 8
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of bis(trifluoromethyl)aniline which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 9
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 10
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 2,2,3,3,4,4-hexafluoro-1,5-pentanediol which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 11
Dependent Claim
179 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of decafluoropropionic anhydride which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 12
Dependent Claim
179 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of decafluoropropionic anhydride which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 13
Dependent Claim
179 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of heptaflluorobutyric anhydride which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 14
Dependent Claim
179 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of heptaflluorobutyric anhydride which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 15
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of tetrafluororesorcinol which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 16
Dependent Claim
178 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of tetrafluororesorcinol which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 17
Dependent Claim
179 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 4,4'-dihydroxyoctafluoro biphenyl which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
Claim 18
Dependent Claim
179 words
A liquid, solvent free epoxy fluorocarbon coating composition curable at temperatures of from about 80° C. to 150° C. comprising about 5 percent to about 24 percent of a fluorocarbon polymer wherein said fluorocarbon polymer is selected from the group consisting of polytetrafluoroethylene, fluorinated ethylene propylene, tetrafluoroethylene, perfluoroalkyloxy resin and combinations thereof, about 25 percent to about 95 percent of an epoxy resin epoxide material or reactive diluent, wherein said epoxy resin is selected from the group consisting of a diglycidyl ether of bisphenol A and a novolak said epoxide material is selected from the group consisting of epoxy resin, cyclohexene oxide, epoxidized cycloalkene, glycidyl esters of acrylic acid, glycidyl alkyl ethers, glycidyl aryl ethers, esters of epoxidized cyclic alcohols and esters of epoxidized cycloalkanecarboxylic acids and said reactive diluent is 1,2-epoxy dodecane and combinations thereof, and about 10 percent to about 70 percent of a fluorinated curing agent of 4,4'-dihydroxyoctafluoro biphenyl which physically integrates fluorine into the backbone of said epoxy resin, epoxide material or reactive diluent, thereby increasing the weight percent of fluorine in said coating composition.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1994-12-23 | 1995-06-24 | 1995-12-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-12-23 | 1999-06-24 | 1999-12-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-12-23 | 2003-06-24 | 2003-12-24 | $7700.00 | Window Closed / Lapsed |