US4554188A
Expired / Lapsed
US
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Chain-extendable crosslinkable urethane modified polyhydroxy oligomers and coating composition comprising same
Assignee: EIDP Inc
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Filing: 1983-01-05
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Granted: 1985-11-19
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Expires: 2003-01-05
Abstract
Abstract High solids, solvent-based resin composition comprises novel chain-extendable, crosslinkable urethane modified polyhydroxy oligomers, crosslinking agent and, preferably, catalyst(s). The composition cures at elevated temperature to provide a coating on a substrate, such as steel, which is highly resistant to corrosion, humidity and solvents and provides corrosion protection for the substrate. The novel oligomers can be the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises three or more hydroxy, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with approximately one molar equivalent of a monofunctional blocking agent.
Inventors
- 👤 Joseph W. Holubka
- 👤 Ray A. Dickie
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 02:34
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/80; C08G18/8061; C08G18/28; C08G18/40; C08G18/48; C08G18/487; C08G18/4875; C08G18/4879; C08G18/50; C08G18/5021; C08G18/5054; C08G18/506; C08G18/64; C08G18/6407; C09; C09D; C09D175/00; C09D175/04; C09D175/08
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
93 words
A solvent-based resin composition comprising: A. chain-extendable crosslinkable urethane modified polyhydroxy oligomer containing no ester linkages and bearing three or more hydroxyl groups and a single blocked isocyanate group, comprising the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises the reaction product of a diepoxide with a diol and bears four or more hydroxyl groups, and said half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with monofunctional blocking agent; B. crosslinking agent reactive with hydroxy functionality and substantially unreactive with isocyanate functionality; and C. organic solvent.
Claim 2
Dependent Claim
93 words
A solvent-based resin composition comprising: A. chain-extendable crosslinkable urethane modified polyhydroxy oligomer containing no ester linkages and bearing three or more hydroxyl groups and a single blocked isocyanate group, comprising the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol comprises the reaction product of a diepoxide with a diol and bears four or more hydroxyl groups, and said half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with monofunctional blocking agent; B. crosslinking agent reactive with hydroxy functionality and substantially unreactive with isocyanate functionality; and C. organic solvent.
Claim 3
Dependent Claim
13 words
The composition of claim 1 wherein said diepoxide bears two terminal epoxide groups.
Claim 4
Dependent Claim
46 words
The composition of claim 1 wherein said diepoxide has a molecular weight between about 100 and about 1000 and is selected from the group consisting of Bisphenol A epichlorohydrin epoxy resin, hydantoin epoxy resin, cyclic or acyclic aliphatic diepoxide and a mixture of any of them.
Claim 5
Dependent Claim
19 words
The composition of claim 1 wherein said diol has a molecular weight of between about 60 and about 500.
Claim 6
Dependent Claim
30 words
The composition of claim 4 wherein said diol is selected from the group consisting of alkyl substituted or unsubstituted propanediol, butanediol, pentanediol, hexanediol and a mixture of any of them.
Claim 7
Dependent Claim
12 words
The composition of claim 5 wherein said diol bears terminal hydroxy functionality.
Claim 8
Dependent Claim
44 words
The composition of claim 1 wherein said diol comprises aromatic diol, wherein each hydroxy is substituted on the same benzene ring or different benzene rings linked through a covalent bond or through one or more carbons of a one to seven carbon aliphatic moiety.
Claim 9
Dependent Claim
27 words
The composition of claim 7 wherein said diol is selected from the group consisting of Bisphenol A, Bisphenol B, catechol and a mixture of any of them.
Claim 10
Dependent Claim
201 words
A solvent-based resin composition comprising: A. a urethane modified polyhydroxy oligomer of molecular weight about 300 to 1100 containing no ester linkages and bearing three or more hydroxyl groups and a single blocked isocyanate group, comprising the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol bears four or more hydroxy groups and comprises the reaction product of an epoxy resin having molecular weight of about 100 to 600 and bearing two epoxy functionality, with alkanediol of two to twenty carbons bearing two terminal hydroxyl groups, and wherein said half-blocked diisocyanate comprises the reaction product of organic diisocyanate selected from the group consisting of toluene diisocyanate, isophorone diisocyanate and a mixture of them, with monofunctional blocking agent selected from the group consisting of alcohol, amide, phenol and a mixture of any of them, said oligomer having an unblocking temperature between about 100° C. and about 190° C.; B. crosslinking agent reactive with hydroxy functionality of said oligomer and substantially unreactive with free isocyanate functionality, selected from the group consisting of polyalkyl ethers of polymethylol melamines, said crosslinking agent and said oligomer being present in a weight ratio of about 1:1 to about 1:5, respectively; and C. organic solvent.
Claim 11
Dependent Claim
201 words
A solvent-based resin composition comprising: A. a urethane modified polyhydroxy oligomer of molecular weight about 300 to 1100 containing no ester linkages and bearing three or more hydroxyl groups and a single blocked isocyanate group, comprising the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol bears four or more hydroxy groups and comprises the reaction product of an epoxy resin having molecular weight of about 100 to 600 and bearing two epoxy functionality, with alkanediol of two to twenty carbons bearing two terminal hydroxyl groups, and wherein said half-blocked diisocyanate comprises the reaction product of organic diisocyanate selected from the group consisting of toluene diisocyanate, isophorone diisocyanate and a mixture of them, with monofunctional blocking agent selected from the group consisting of alcohol, amide, phenol and a mixture of any of them, said oligomer having an unblocking temperature between about 100° C. and about 190° C.; B. crosslinking agent reactive with hydroxy functionality of said oligomer and substantially unreactive with free isocyanate functionality, selected from the group consisting of polyalkyl ethers of polymethylol melamines, said crosslinking agent and said oligomer being present in a weight ratio of about 1:1 to about 1:5, respectively; and C. organic solvent.
Claim 12
Dependent Claim
24 words
The resin composition of claim 9 wherein said blocking agent is selected from the group consisting of butanol, 2-ethylhexanol, and a mixture of them.
Claim 13
Dependent Claim
12 words
The resin composition of claim 9 wherein said crosslinking agent is hexamethoxymethylmelamine.
Claim 14
Dependent Claim
20 words
The resin composition of claim 9 further comprising from about 0.1% to about 1% by weight catalyst comprising paratoluenesulfonic acid.
Claim 15
Dependent Claim
21 words
The resin composition of claim 9 further comprising from about 0.1% to about 1% by weight catalyst comprising dibutyl tin dilaurate.
Claim 16
Dependent Claim
11 words
The resin composition of claim 9 wherein said alkanediol is 2-ethyl-1,3-hexanediol.
Claim 17
Dependent Claim
11 words
The resin composition of claim 9 wherein said alkanediol is 1,5-pentanediol.
Claim 18
Dependent Claim
16 words
The resin composition of claim 9 wherein said epoxy resin is Bisphenol A epichlorohydrin epoxy resin.
Claim 19
Dependent Claim
14 words
The resin composition of claim 9 wherein said epoxy resin is cycloaliphatic diepoxy resin.
Claim 20
Independent Claim
147 words
A method of making a corrosion, humidity and solvent resistant coating on a substrate, which method comprises applying to said substrate a solvent-based thermosetting coating composition comprising: A. a chain-extendable, crosslinkable urethane modified polyhydroxy oligomer containing no ester linkages and bearing three or more hydroxyl groups and a single blocked isocyanate group, comprising the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol bears four or more hydroxyl groups, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with monofunctional blocking agent, wherein said monofunctional blocking agent has a de-blocking temperature of between about 100° C. and about 190° C.; B. crosslinking agent reactive with said hydroxy functionality of said oligomer and substantially unreactive with said isocyanate functionality; and C. organic solvent; and heating said composition to at least about 100° C. for a period of sufficient to cure said composition.
Claim 21
Independent Claim
147 words
A method of making a corrosion, humidity and solvent resistant coating on a substrate, which method comprises applying to said substrate a solvent-based thermosetting coating composition comprising: A. a chain-extendable, crosslinkable urethane modified polyhydroxy oligomer containing no ester linkages and bearing three or more hydroxyl groups and a single blocked isocyanate group, comprising the reaction product of a polyol with a half-blocked diisocyanate, wherein said polyol bears four or more hydroxyl groups, and the half-blocked diisocyanate comprises the reaction product of an organic diisocyanate with monofunctional blocking agent, wherein said monofunctional blocking agent has a de-blocking temperature of between about 100° C. and about 190° C.; B. crosslinking agent reactive with said hydroxy functionality of said oligomer and substantially unreactive with said isocyanate functionality; and C. organic solvent; and heating said composition to at least about 100° C. for a period of sufficient to cure said composition.
Claim 22
Dependent Claim
21 words
A corrosion, humidity and solvent resistant coating on a substrate, which coating is made according to the method of claim 18.
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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) | 1988-11-18 | 1989-05-20 | 1989-11-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-11-18 | 1993-05-20 | 1993-11-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-11-18 | 1997-05-20 | 1997-11-19 | $7700.00 | Window Closed / Lapsed |