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US4206104A
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N,N-'-Dihydroxyalkyl ester substituted imidazolidinediones and coating compositions containing same
Assignee: PPG Industries Inc
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Filing: 1978-10-10
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Granted: 1980-06-03
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Expires: 1998-10-10
Abstract
Abstract Resin mixtures of N,N'-dihydroxyalkyl ester substituted imidazolidinediones are especially useful in coating compositions having a low organic solvent content. The substituted imidazolidinediones have the formula ##STR1## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms, X is ##STR2## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
Inventors
- 👤 Rostyslaw Dowbenko
- 👤 Ronald J. Lewarchik
- 👤 William J. Birkmeyer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 14:08
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C07D233/76; C07D233/78; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3842; C08G18/3848; C09; C09D; C09D161/00; C09D161/04; C09D161/06; C09D161/20; Y; Y10; Y10S; Y10S525/00; Y10S525/908; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31688
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
47 words
A resin mixture of N,N'-dihydroxyalkyl ester substituted imidazolidinediones having the formula: ##STR9## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms, X is ##STR10## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
Claim 2
Dependent Claim
47 words
A resin mixture of N,N'-dihydroxyalkyl ester substituted imidazolidinediones having the formula: ##STR9## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms, X is ##STR10## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
Claim 3
Dependent Claim
12 words
The resin mixture of claim 1, wherein R and R' are hydrogens.
Claim 4
Dependent Claim
13 words
The resin mixture of claim 1, wherein R and R' are alkyl groups.
Claim 5
Dependent Claim
17 words
The resin mixture of claim 3, wherein the alkyl groups have from 1 to 5 carbon atoms.
Claim 6
Dependent Claim
17 words
The resin mixture of claim 4, wherein the alkyl groups are joined to form a cycloalkyl group.
Claim 7
Dependent Claim
16 words
The resin mixture of claim 1, wherein R is hydrogen and R' is an alkyl group.
Claim 8
Dependent Claim
16 words
The resin mixture of claims 2, 3 or 6, wherein the R" groups are alkyl groups.
Claim 9
Dependent Claim
18 words
The resin mixture of claim 7, wherein the R" alkyl groups have from 7 to 17 carbon atoms.
Claim 10
Dependent Claim
15 words
The resin mixture of claim 8, wherein the R" alkyl groups are tertiary alkyl groups.
Claim 11
Dependent Claim
16 words
The resin mixture of claims 2, 3 or 6, wherein the R" groups are alkenyl groups.
Claim 12
Dependent Claim
25 words
The resin mixture of claims 2, 3 or 6, wherein the R" groups are aryl or alkylaryl groups having from 6 to 10 carbon atoms.
Claim 13
Dependent Claim
106 words
A process for making a resin mixture of N,N'-dihydroxyalkyl ester substituted imidazolidinediones comprising the step of reacting (1) an imidazolidinedione of the formula: ##STR11## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms; with (2) a glycidyl ester of the formula: ##STR12## wherein R" is a hydrocarbon group having from 1 to 17 carbon atoms at a temperature of from about 50° C. to about 200° C. in the presence of a catalyst so as to obtain a mixture of compounds having the formula: ##STR13## where X is ##STR14## with R, R' and R" being as defined above.
Claim 14
Dependent Claim
106 words
A process for making a resin mixture of N,N'-dihydroxyalkyl ester substituted imidazolidinediones comprising the step of reacting (1) an imidazolidinedione of the formula: ##STR11## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms; with (2) a glycidyl ester of the formula: ##STR12## wherein R" is a hydrocarbon group having from 1 to 17 carbon atoms at a temperature of from about 50° C. to about 200° C. in the presence of a catalyst so as to obtain a mixture of compounds having the formula: ##STR13## where X is ##STR14## with R, R' and R" being as defined above.
Claim 15
Dependent Claim
11 words
The process of claim 12, wherein R and R' are hydrogens.
Claim 16
Dependent Claim
12 words
The process of claim 12, wherein R and R' are alkyl groups.
Claim 17
Dependent Claim
18 words
The process of claim 14, wherein the R and R' groups have from 1 to 5 carbon atoms.
Claim 18
Dependent Claim
19 words
The process of claim 15, wherein the R and R' alkyl groups are joined to form a cycloalkyl group.
Claim 19
Dependent Claim
15 words
The process of claim 12, wherein R is hydrogen and R' is an alkyl group.
Claim 20
Dependent Claim
22 words
The process of claims 13, 14, or 17, wherein the R" groups are alkyl groups have from 7 to 17 carbon atoms.
Claim 21
Dependent Claim
99 words
A coating composition containing less than about 40 percent organic solvent, consisting essentially of: (a) from about 5 percent to about 90 percent of a resin mixture of N,N'-dihydroxyalkyl ester substituted imidazolidinediones having the formula: ##STR15## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms, X is ##STR16## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms; and (b) from about 5 percent to about 80 percent of a crosslinking agent selected from the group consisting of aminoplasts, isocyanates, blocked isocyanates, phenoplasts and mixtures thereof.
Claim 22
Dependent Claim
99 words
A coating composition containing less than about 40 percent organic solvent, consisting essentially of: (a) from about 5 percent to about 90 percent of a resin mixture of N,N'-dihydroxyalkyl ester substituted imidazolidinediones having the formula: ##STR15## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms, X is ##STR16## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms; and (b) from about 5 percent to about 80 percent of a crosslinking agent selected from the group consisting of aminoplasts, isocyanates, blocked isocyanates, phenoplasts and mixtures thereof.
Claim 23
Dependent Claim
16 words
The composition of claim 19, wherein the composition contains less than about 30 percent organic solvent.
Claim 24
Dependent Claim
11 words
The composition of claim 19, wherein R and R' are hydrogens.
Claim 25
Dependent Claim
12 words
The composition of claim 19, wherein R and R' are alkyl groups.
Claim 26
Dependent Claim
16 words
The composition of claim 22, wherein the alkyl groups have from 1 to 5 carbon atoms.
Claim 27
Dependent Claim
16 words
The composition of claim 23, wherein the alkyl groups are joined to form a cycloalkyl group.
Claim 28
Dependent Claim
15 words
The composition of claim 19, wherein R is hydrogen and R' is an alkyl group.
Claim 29
Dependent Claim
15 words
The composition of claims 21, 22, or 25, wherein the R" groups are alkyl groups.
Claim 30
Dependent Claim
17 words
The composition of claim 26, wherein the R" alkyl groups have from 7 to 17 carbon atoms.
Claim 31
Dependent Claim
15 words
The composition of claims 21, 22 or 25, wherein the R" groups are alkenyl groups.
Claim 32
Dependent Claim
24 words
The composition of claims 21, 22, or 25, wherein the R" groups are aryl or alkylaryl groups having from 6 to 10 carbon atoms.
Claim 33
Dependent Claim
12 words
The composition of claim 19, wherein the crosslinking agent is an aminoplast.
Claim 34
Dependent Claim
13 words
The composition of claim 19, wherein the crosslinking agent is a blocked isocyanate.
Claim 35
Dependent Claim
38 words
The composition of claims 19, 30 or 31, wherein the substituted imidazolidinediones represent from about 10 percent to 50 percent of the composition and the crosslinking agent from about 20 percent to about 60 percent of the composition.
Claim 36
Dependent Claim
24 words
The process of claim 12 wherein the catalyst is a tertiary amine, quaternary phosphonium salt, quaternary ammonium salt, butyl stannoic acid or para-toluenesulfonic acid.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-06-03 | 1983-12-03 | 1984-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-03 | 1987-12-03 | 1988-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-03 | 1991-12-03 | 1992-06-03 | $7700.00 | Window Closed / Lapsed |