US4423171A
Expired / Lapsed
US
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Tertiary alcohol-diblocked diisocyanate diurea oligomers and coating compositions comprising same
Assignee: EIDP Inc
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Filing: 1981-12-28
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Granted: 1983-12-27
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Expires: 2001-12-28
Abstract
Abstract This invention provides polymer forming resin systems and high solids solvent based chain-extendable, crosslinkable coating compositions comprising same. The invention comprises a polyepoxide, preferably a diepoxide, of molecular weight between about 100 and about 1000 used generally in amounts from about 10% to about 50% by weight of total resin, and novel diblocked diisocyanate diurea oligomers of molecular weight between about 300 and about 5000. The resin components provide chain-extension polymerization during cure at elevated temperature, in situ, on the surface of a substrate. The resin system is self-crosslinking. That is, no additional crosslinking component is required. The cured coatings of the invention provide greatly improved physical properties, in particular greatly improved corrosion resistance.
Inventors
- 👤 Joseph W. Holubka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 05:40
CPC Classifications
C; C09; C09D; C09D163/00; C07; C07C; C07C275/00; C07C275/26; C07C275/28; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/58; C08G18/70; C08G18/72; C08G18/80; C08G18/8003; C08G18/8006; C08G18/8038; C08G18/8061; C08G18/8064; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4028
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
92 words
A chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of number average molecular weight about 300 to about 5000 comprising the reaction product of diamine of molecular weight about 50 to about 700, with half-blocked organic diisocyanate of molecular weight about 120 to about 2000 in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of an alcohol blocking agent bearing a tertiary hydroxyl group, with organic diisocyanate in molar ratio of about 1:1, said oligomer having a de-blocking temperature of about 80° C. to about 220° C.
Claim 2
Dependent Claim
92 words
A chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of number average molecular weight about 300 to about 5000 comprising the reaction product of diamine of molecular weight about 50 to about 700, with half-blocked organic diisocyanate of molecular weight about 120 to about 2000 in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of an alcohol blocking agent bearing a tertiary hydroxyl group, with organic diisocyanate in molar ratio of about 1:1, said oligomer having a de-blocking temperature of about 80° C. to about 220° C.
Claim 3
Dependent Claim
26 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said oligomer has a number average molecular weight of about 300 to about 1500.
Claim 4
Dependent Claim
26 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said oligomer has a deblocking temperature of about 110° C. to about 180° C.
Claim 5
Dependent Claim
33 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said diamine comprises alkylenediamine wherein the alkylene moiety is straight or branched chain and has about 2 to about 20 carbons.
Claim 6
Dependent Claim
19 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 4 wherein said diamine bears two terminal amine group.
Claim 7
Dependent Claim
25 words
The oligomer of claim 5 wherein said diamine is selected from the group consisting of 1,6-hexanediamine, 1,5-pentanediamine, 1,4-butanediamine and a mixture of any of them.
Claim 8
Dependent Claim
29 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said diamine comprises cycloaliphatic diamines of about 4 to about 20 carbons or a mixture of them.
Claim 9
Dependent Claim
17 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 7 wherein said diamine is isophorone diamine.
Claim 10
Dependent Claim
51 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said diamine comprises aromatic diamine wherein each amine is substituted on the same benzene ring or on different benezene rings linked through a covalent bond or through one or more carbons of a one to seven carbon aliphatic moiety.
Claim 11
Dependent Claim
29 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 9 wherein said diamine is selected from the group consisting of toluene diamine, 4,4'methylenedianiline and a mixture of them.
Claim 12
Dependent Claim
18 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 10 wherein said diamine consists of toluene diamine.
Claim 13
Dependent Claim
34 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said tertiary alcohol is selected from the group consisting of t-butanol, 2-methyl-2-hydroxybutane, 2-methyl-2-hydroxypentane, 2-methyl-2-hydroxyhexane, 1-methylcyclohexanol and a mixture of any of them.
Claim 14
Dependent Claim
22 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said tertiary alcohol has about four to about 20 carbons.
Claim 15
Dependent Claim
43 words
The chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of claim 1 wherein said organic diisocyanate is selected from phenylene diisocyanate, toluene diisocyanate, isophorone diisocyanate, diisocyanatoalkane wherein the alkylene moiety has about 3 to about 10 carbons and a mixture of any of them.
Claim 16
Dependent Claim
138 words
A solvent based resin composition comprising: A. a chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of number average molecular weight about 300 to about 5000 comprising the reaction product of diamine of molecular weight of about 50 to about 700, with half-blocked organic diisocyanate of molecular weight about 120 to about 2000 in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of an alcohol of 4 to 20 carbons bearing a tertiary hydroxyl group, with organic diisocyanate in molar ratio of about 1:1, said oligomer having de-blocking temperature of about 80° C. to about 220° C.; B. polyepoxide having 2 to about 10 epoxide groups and having a molecular weight of about 100 to about 1000, in weight ratio to said oligomer of about 1:1 to about 1:10; and C. organic solvent.
Claim 17
Dependent Claim
138 words
A solvent based resin composition comprising: A. a chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of number average molecular weight about 300 to about 5000 comprising the reaction product of diamine of molecular weight of about 50 to about 700, with half-blocked organic diisocyanate of molecular weight about 120 to about 2000 in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of an alcohol of 4 to 20 carbons bearing a tertiary hydroxyl group, with organic diisocyanate in molar ratio of about 1:1, said oligomer having de-blocking temperature of about 80° C. to about 220° C.; B. polyepoxide having 2 to about 10 epoxide groups and having a molecular weight of about 100 to about 1000, in weight ratio to said oligomer of about 1:1 to about 1:10; and C. organic solvent.
Claim 18
Dependent Claim
21 words
The resin composition of claim 15 wherein said oligomer has a number average molecular weight of about 300 to about 1500.
Claim 19
Dependent Claim
21 words
The resin composition of claim 15 wherein said oligomer has a deblocking temperature of about 110° C. to about 180° C.
Claim 20
Dependent Claim
28 words
The resin composition of claim 15 wherein said diamine comprises alkylenediamine wherein the alkylene moiety is straight or branched chain and has about 2 to about 20 carbons.
Claim 21
Dependent Claim
14 words
The resin composition of claim 18 wherein said diamine bears two terminal amine group.
Claim 22
Dependent Claim
26 words
The resin composition of claim 19 wherein said diamine is selected from the group consisting of 1,6-hexanediamine, 1,5-pentanediamine, 1,4-butanediamine and a mixture of any of them.
Claim 23
Dependent Claim
24 words
The resin composition of claim 15 wherein said diamine comprises cycloaliphatic diamines of about 4 to about 20 carbons or a mixture of them.
Claim 24
Dependent Claim
12 words
The resin composition of claim 21 wherein said diamine is isophorone diamine.
Claim 25
Dependent Claim
46 words
The resin composition of claim 15 wherein said diamine comprises aromatic diamine wherein each amine is substituted on the same benzene ring or on different benezene rings linked through a covalent bond or through one or more carbons of a one to seven carbon aliphatic moiety.
Claim 26
Dependent Claim
24 words
The resin composition of claim 23 wherein said diamine is selected from the group consisting of toluene diamine, 4,4'methylenedianiline and a mixture of them.
Claim 27
Dependent Claim
29 words
The resin composition of claim 15 wherein said tertiary alcohol is selected from the group consisting of t-butanol, 2-methyl-2-hydroxybutane, 2-methyl-2-hydroxypentane, 2-methyl-2-hydroxyhexane, 1-methylcyclohexanol and a mixture of any of them.
Claim 28
Dependent Claim
17 words
The resin composition of claim 15 wherein said tertiary alcohol has about four to about 20 carbons.
Claim 29
Dependent Claim
38 words
The resin composition of claim 15 wherein said organic diisocyanate is selected from phenylene diisocyanate, toluene diisocyanate, isophorone diisocyanate, diisocyanatoalkane wherein the alkylene moiety has about 3 to about 10 carbons and a mixture of any of them.
Claim 30
Dependent Claim
16 words
The resin composition of claim 15 wherein said polyepoxide has 2 to about 4 epoxide groups.
Claim 31
Dependent Claim
14 words
The resin composition of claim 15 wherein said polyepoxide bears two terminal epoxide groups.
Claim 32
Dependent Claim
11 words
The resin composition of claim 15 wherein said polyepoxide comprises diepoxide.
Claim 33
Dependent Claim
41 words
The resin composition of claim 30 wherein said diepoxide is selected from the group consisting of 1,4-butanediol diglycidyl ether, 4-vinylcyclohexenedioxide, Bisphenol A epichlorohydrin epoxy resin, cycloaliphatic diepoxy resin, hydantoin epoxy resin, epoxy novalak resin and a mixture of any of them.
Claim 34
Dependent Claim
24 words
The resin composition of claim 15 wherein said oligomer and said polyepoxide are present in molar equivalent ratio of about 1:1 to about 2:1.
Claim 35
Dependent Claim
31 words
The resin composition of claim 15 wherein said organic solvent is selected from the group consisting of butanol, methyl ethyl ketone, methyl amyl ketone and a mixture of any of them.
Claim 36
Dependent Claim
142 words
A solvent based resin composition comprising: A. the reaction product of diamine selected from the group consisting of 1,6-hexanediamine, 1,5-pentanediamine, 1,4-butanediamine, isophorone diamine, toluene diamine, methylenedianiline and a mixture of any of them, with half-blocked organic diisocyanate in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of tertiary butanol with an approximately equal molar amount of organic diisocyanate of molecular weight less than about 250, said oligomer having a number average molecular weight of about 300 to about 1500 and de-blocking temperature of about 110° C. to about 180° C.; B. polyepoxide of molecular weight about 300 to about 700, in weight ratio to said oligomer of about 1:1 to about 1:2, respectively; and C. organic solvent in such amount that said resin composition has a volatile organic content (calculated) of less than about 400 g/l.
Claim 37
Dependent Claim
142 words
A solvent based resin composition comprising: A. the reaction product of diamine selected from the group consisting of 1,6-hexanediamine, 1,5-pentanediamine, 1,4-butanediamine, isophorone diamine, toluene diamine, methylenedianiline and a mixture of any of them, with half-blocked organic diisocyanate in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of tertiary butanol with an approximately equal molar amount of organic diisocyanate of molecular weight less than about 250, said oligomer having a number average molecular weight of about 300 to about 1500 and de-blocking temperature of about 110° C. to about 180° C.; B. polyepoxide of molecular weight about 300 to about 700, in weight ratio to said oligomer of about 1:1 to about 1:2, respectively; and C. organic solvent in such amount that said resin composition has a volatile organic content (calculated) of less than about 400 g/l.
Claim 38
Dependent Claim
42 words
The resin composition of claim 34 wherein said organic diisocyanate is selected from the group consisting of toluene diisocyanate, phenylene diisocyanate, isophorone diisocyanates, diisocyanatoalkane wherein the alkylene moiety has about 3 to about 10 carbons and a mixture of any of them.
Claim 39
Independent Claim
182 words
A method of making a corrosion, humidity and solvent resistant coating in situ, on the surface of a substrate, which method comprises applying to said surface a solvent based resin composition comprising: A. a chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of number average molecular weight of about 300 to about 5000 comprising the reaction product of diamine of molecular weight about 50 to about 700, with half-blocked organic diisocyanate of molecular weight about 120 to about 2000 in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of an alcohol blocking agent bearing a tertiary hydroxyl group, with organic diisocyanate in molar ratio of about 1:1, said oligomer having de-blocking temperature of about 80° C. to about 220° C.; B. polyepoxide having about 2 to about 10 epoxide groups and having a molecular weight of about 100 to about 1000, in weight ratio to said oligomer of about 1:1 to about 1:10; and C. organic solvent; and heating said composition at about 80° C. to about 220° C. for a time sufficient to cure said composition.
Claim 40
Independent Claim
182 words
A method of making a corrosion, humidity and solvent resistant coating in situ, on the surface of a substrate, which method comprises applying to said surface a solvent based resin composition comprising: A. a chain-extendable, crosslinkable tertiary alcohol-diblocked diisocyanate diurea oligomer of number average molecular weight of about 300 to about 5000 comprising the reaction product of diamine of molecular weight about 50 to about 700, with half-blocked organic diisocyanate of molecular weight about 120 to about 2000 in molar ratio of about 1:2, respectively, said half-blocked organic diisocyanate comprising the reaction product of an alcohol blocking agent bearing a tertiary hydroxyl group, with organic diisocyanate in molar ratio of about 1:1, said oligomer having de-blocking temperature of about 80° C. to about 220° C.; B. polyepoxide having about 2 to about 10 epoxide groups and having a molecular weight of about 100 to about 1000, in weight ratio to said oligomer of about 1:1 to about 1:10; and C. organic solvent; and heating said composition at about 80° C. to about 220° C. for a time sufficient to cure said composition.
Claim 41
Dependent Claim
23 words
A corrosion, humidity and solvent resistant coating made, in situ, on the surface of a substrate according to the method of claim 36.
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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) | 1986-12-26 | 1987-06-27 | 1987-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-26 | 1991-06-27 | 1991-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-26 | 1995-06-27 | 1995-12-27 | $7700.00 | Window Closed / Lapsed |