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US4174337A
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Hydroxy-functional esters of substituted imidazolidinediones and compositions containing same
Assignee: PPG Industries Inc
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Filing: 1978-10-10
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Granted: 1979-11-13
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Expires: 1998-10-10
Abstract
Abstract Hydroxy-functional esters of substituted imidazolidinediones have the formula: ##STR1## where X is hydrogen, ##STR2## provided both X's are not hydrogen, where R and R' are independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR3## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms. The novel compounds are especially useful when formulated with a crosslinking agent and used in low organic solvent-containing coating compositions.
Inventors
- 👤 William J. Birkmeyer
- 👤 J. Alden Erikson
- 👤 Ronald J. Lewarchik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 08:27
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/72; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3842; C08G18/3848
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
70 words
A hydroxy-functional ester of a substituted imidazolidinedione having the formula: ##STR12## where X is hydrogen, ##STR13## provided both X's are not hydrogen, with R and R' being independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR14## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
Claim 2
Dependent Claim
70 words
A hydroxy-functional ester of a substituted imidazolidinedione having the formula: ##STR12## where X is hydrogen, ##STR13## provided both X's are not hydrogen, with R and R' being independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR14## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
Claim 3
Dependent Claim
11 words
The ester of claim 1 wherein R and R' are hydrogens.
Claim 4
Dependent Claim
12 words
The ester of claim 1 wherein R and R' are alkyl groups.
Claim 5
Dependent Claim
16 words
The ester of claim 3 wherein the alkyl groups have from 1 to 5 carbon atoms.
Claim 6
Dependent Claim
16 words
The ester of claim 4 wherein R and R' are joined to form a cycloalkyl group.
Claim 7
Dependent Claim
15 words
The ester of claim 1 wherein R is hydrogen and R' is an alkyl group.
Claim 8
Dependent Claim
15 words
The ester of claims 2, 3 or 6 wherein the R" groups are alkyl groups.
Claim 9
Dependent Claim
17 words
The ester of claim 7 wherein the R" alkyl groups have from 7 to 17 carbon atoms.
Claim 10
Dependent Claim
15 words
The ester of claims 2, 3 or 6 wherein the R" groups are alkenyl groups.
Claim 11
Dependent Claim
24 words
The ester of claims 2, 3 or 6 wherein the R" groups are aryl or alkylaryl groups having from 6 to 10 carbon atoms.
Claim 12
Dependent Claim
13 words
The ester of claims 2, 3 or 6 wherein neither X is hydrogen.
Claim 13
Dependent Claim
141 words
A process for making a hydroxy-functional ester of a substituted imidazolidinedione comprising the steps of (a) reacting a 1,3-diglycidyl-2,4-imidazolidinedione having the formula: ##STR15## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms with a 2,4-imidazolidinedione of the formula: ##STR16## wherein R and R' are as defined previously; and (b) reacting the compound of step (a) with a carboxylic acid having from 2 to 18 carbon atoms to obtain the ester having the formula: ##STR17## where X is hydrogen, ##STR18## provided both X's are not hydrogen, where R and R' are independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR19## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
Claim 14
Dependent Claim
141 words
A process for making a hydroxy-functional ester of a substituted imidazolidinedione comprising the steps of (a) reacting a 1,3-diglycidyl-2,4-imidazolidinedione having the formula: ##STR15## wherein R and R' are independently hydrogen or hydrocarbon groups having from 1 to 8 carbon atoms with a 2,4-imidazolidinedione of the formula: ##STR16## wherein R and R' are as defined previously; and (b) reacting the compound of step (a) with a carboxylic acid having from 2 to 18 carbon atoms to obtain the ester having the formula: ##STR17## where X is hydrogen, ##STR18## provided both X's are not hydrogen, where R and R' are independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR19## where the R" groups are independently hydrocarbon groups having from 1 to 17 carbon atoms.
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
19 words
The process of claim 14 wherein the R and R' alkyl groups have from 1 to 5 carbon atoms.
Claim 18
Dependent Claim
19 words
The process of claim 15 wherein the R and R' groups are joined together 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 having from 7 to 17 carbon atoms.
Claim 21
Dependent Claim
10 words
The process of claim 18 wherein neither X is hydrogen.
Claim 22
Dependent Claim
122 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 hydroxy-functional ester of a substituted imidazolidinedione of the formula: ##STR20## where X is hydrogen, ##STR21## provided both X's are not hydrogen, where R and R' are independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR22## 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
122 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 hydroxy-functional ester of a substituted imidazolidinedione of the formula: ##STR20## where X is hydrogen, ##STR21## provided both X's are not hydrogen, where R and R' are independently hydrogen or hydrocarbon groups having 1 to 8 carbon atoms, with one Y being hydrogen, one Z being hydrogen and the other Y and Z being ##STR22## 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 24
Dependent Claim
12 words
The coating composition of claim 20 wherein R and R' are hydrogens.
Claim 25
Dependent Claim
13 words
The coating composition of claim 20 wherein R and R' are alkyl groups.
Claim 26
Dependent Claim
17 words
The coating composition of claim 22 wherein the alkyl groups have from 1 to 5 carbon atoms.
Claim 27
Dependent Claim
17 words
The coating composition of claim 23 wherein R and R' are joined to form a cycloalkyl group.
Claim 28
Dependent Claim
16 words
The coating composition of claim 20 wherein R is hydrogen and R' is an alkyl group.
Claim 29
Dependent Claim
16 words
The coating composition of claims 21, 22 or 25 wherein the R" groups are alkyl groups.
Claim 30
Dependent Claim
18 words
The coating composition of claim 26 wherein the R" alkyl groups have from 7 to 17 carbon atoms.
Claim 31
Dependent Claim
16 words
The coating composition of claims 21, 22 or 25 wherein the R" groups are alkenyl groups.
Claim 32
Dependent Claim
25 words
The coating 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
14 words
The coating composition of claims 21, 22 or 25 wherein neither X is hydrogen.
Claim 34
Dependent Claim
13 words
The coating composition of claim 30 wherein the crosslinking agent is an aminoplast.
Claim 35
Dependent Claim
14 words
The coating composition of claim 30 wherein the crosslinking agent is a blocked isocyanate.
Claim 36
Dependent Claim
21 words
The coating composition of claim 31 wherein the level of organic solvent in the composition is less than about 30 percent.
Claim 37
Dependent Claim
36 words
The coating composition of claim 33 wherein the composition consists essentially of from about 10 percent to about 50 percent of the ester and from about 20 percent to about 60 percent of the crosslinking agent.
References Cited (Backward Citations)
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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) | 1982-11-12 | 1983-05-14 | 1983-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-12 | 1987-05-14 | 1987-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-12 | 1991-05-14 | 1991-11-13 | $7700.00 | Window Closed / Lapsed |