US4507445A
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US
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Heat-curable epoxide resin compositions
Assignee: Novartis Corp
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Filing: 1983-09-30
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Granted: 1985-03-26
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Expires: 2003-09-30
Abstract
Abstract Epoxide resins are cured by heating with a hydroxyphenylurea of formula ##STR1## where R 2 denotes --NH 2 , --NO 2 , --Cl, --Br, or alkyl, p denotes zero, x and y each denote zero or 1, and the sum of x+y is 1. Such hydroxyphenylureas may be used alone, as accelerators for heat-curing with other agents such as dicyandiamide, melamine, and carboxylic acid hydrazides, or may be used as the primary curing agent with promoters such as dicyandiamide, melamine, and carboxylic hydrazides.
Inventors
- 👤 Christopher M. Andrews
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 08:43
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4021; C08G59/62; C08G59/621; C08G59/623; C08G59/68; C08G59/686
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
60 words
A heat-curable composition comprising (a) an epoxide resin and (b) an effective amount of a urea of formula ##STR7## where R 2 denotes --NH 2 , --NO 2 , --Cl, --Br, or alkyl of 1 to 10 carbon atoms, p denotes zero, 1, or 2, x and y each denote zero or 1, and the sum of x+y is 1.
Claim 2
Dependent Claim
60 words
A heat-curable composition comprising (a) an epoxide resin and (b) an effective amount of a urea of formula ##STR7## where R 2 denotes --NH 2 , --NO 2 , --Cl, --Br, or alkyl of 1 to 10 carbon atoms, p denotes zero, 1, or 2, x and y each denote zero or 1, and the sum of x+y is 1.
Claim 3
Dependent Claim
37 words
A composition according to claim 1, in which p is zero, or 1 with R 2 denoting --NO 2 , --Cl, or --CH 3 , or in which p is 2 with each R 2 denoting --Cl.
Claim 4
Dependent Claim
17 words
A composition according to claim 1, in which (b) is N-(3-hydroxyphenyl)-N',N'-dimethylurea, N-(4,6-dichloro-3-hydroxyphenyl)-N',N'-dimethylurea, N-(4-hydroxyphenyl)-N',N'-dimethylurea, N-(4-hydroxy-2-methylphenyl)-N',N'-dimethylurea, N-(4-hydroxy-3-nitrophenyl)-N',N'-dimethylurea or N-(3,5-dichloro-4-hydroxyphenyl)-N',N'-dimethylurea.
Claim 5
Dependent Claim
12 words
A composition according to claim 1, containing a heat-curing amount of (b).
Claim 6
Dependent Claim
23 words
A composition according to claim 4, containing from 3 to 25 parts by weight of (b) per 100 parts by weight of (a).
Claim 7
Dependent Claim
63 words
A composition according to claim 1, which further contains (c) a minor amount by weight, calculated on the weight of (b), of an accelerator for the heat-curing, selected from the group consisting of dicyandiamide, carboxylic acid hydrazides, succinimide, cyanoacetamide, 1-cyano-3-(lower alkyl)guanidines wherein the lower alkyl group or groups contain up to 3 carbon atoms, imidazoles, and salts of carboxylic acids with tertiary amines.
Claim 8
Dependent Claim
23 words
A composition according to claim 6, containing from 10 to 50 parts by weight of (c) per 100 parts by weight of (b).
Claim 9
Dependent Claim
25 words
A composition according to claim 6, in which the carboxylic acid hydrazide is stearic hydrazide, oxalic acid dihydrazide, adipic acid dihydrazide, or isophthalic acid dihydrazide.
Claim 10
Dependent Claim
15 words
A composition according to claim 6, in which the imidazole is 2-phenylimidazole, N-methylimidazole, or 2-ethyl-4-methylimidazole.
Claim 11
Dependent Claim
61 words
A composition according to claim 1, which further contains (d) a major amount by weight, calculated on the weight of (b), of a heat-curing agent selected from the group consisting of dicyandiamide, carboxylic acid hydrazides, succinimide, cyanoacetamide, 1-cyano-3-(lower alkyl)guanidines wherein the lower alkyl group or groups contain up to 3 carbon atoms, imidazoles, and salts of carboxylic acids with tertiary amines.
Claim 12
Dependent Claim
23 words
A composition according to claim 10, containing from 25 to 75 parts by weight of (b) per 100 parts by weight of (d).
Claim 13
Dependent Claim
25 words
A composition according to claim 10, in which the carboxylic acid hydrazide is stearic hydrazide, oxalic acid dihydrazide, adipic acid dihydrazide or isophthalic acid dihydrazide.
Claim 14
Dependent Claim
15 words
A composition according to claim 10, in which the imidazole is 2-phenylimidazole, N-methylimidazole, or 2-ethyl-4-methylimidazole.
Claim 15
Dependent Claim
76 words
A composition according to claim 1, in which (a) contains at least two groups of formula ##STR8## directly attached to an atom or atoms of oxygen, nitrogen or sulphur, where either R 3 and R 5 each represent a hydrogen atom, in which case R 4 represents a hydrogen atom or a methyl group, or R 3 and R 5 together represent --CH 2 CH 2 --, in which case R 4 denotes a hydrogen atom.
Claim 16
Dependent Claim
26 words
A composition according to claim 14, in which (a) is a polyglycidyl ether, a polyglycidyl ester, an N,N'-diglycidylhydantoin, or a poly(N-glycidyl) derivative of an aromatic amine.
Claim 17
Dependent Claim
66 words
A composition according to claim 15, in which (a) is a polyglycidyl ether of 2,2-bis(4-hydroxyphenyl)propane, of bis(4-hydroxyphenyl)methane, or of a novolak formed from formaldehyde and phenol, or phenol substituted in the ring by one chlorine atom or by one alkyl hydrocarbon group containing from one to nine carbon atoms, and having a 1,2-epoxide content of at least 0.5 equivalent per kilogram, bis(4-(diglycidylamino)phenyl)methane, or p-(diglycidylamino)phenyl glycidyl ether.
Claim 18
Dependent Claim
28 words
A process for curing an epoxide resin, comprising (i) forming a composition as claimed in claim 1 and (ii) heating the composition until the epoxide resin is cured.
Claim 19
Dependent Claim
18 words
A process according to claim 17, in which the composition is heated at from 100° to 180° C.
Claim 20
Dependent Claim
18 words
A process according to claim 17, in which the composition is heated for from 30 to 120 minutes.
Claim 21
Dependent Claim
12 words
A cured product obtained by a process as claimed in claim 17.
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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) | 1988-03-25 | 1988-09-24 | 1989-03-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-25 | 1992-09-24 | 1993-03-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-25 | 1996-09-24 | 1997-03-26 | $7700.00 | Window Closed / Lapsed |