US4168364A
Expired / Lapsed
US
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Cyanamides of organic primary amines as epoxy curing agents
Assignee: BASF Corp
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Filing: 1978-08-15
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Granted: 1979-09-18
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Expires: 1998-08-15
Abstract
Abstract Curable compositions are prepared comprising an epoxide compound or a mixture of epoxide compounds having an average of at least two epoxide groups per molecule, and as a curing agent, a cyanamide of an organic primary amine or a mixture of cyanamides of organic primary amines having an average of more than one cyanamide moiety per molecule. Such compositions are useful in molding, casting, laminating and coating applications.
Inventors
- 👤 Raymond Seltzer
- 👤 Joseph F. DiPrima
- 👤 William S. Durrell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 11:27
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
68 words
A heat curable composition comprising: (a) a 1,2-epoxide compound or a mixture of epoxide compounds having an average of at least two epoxide groups per molecule; and (b) a cyanamide of organic primary amine or mixture of cyanamides of organic primary amines having an average of more than one cyanamide moiety per molecule; wherein one mole of cyanamide is employed to cure 0.1 to 4.0 moles of epoxide.
Claim 2
Dependent Claim
68 words
A heat curable composition comprising: (a) a 1,2-epoxide compound or a mixture of epoxide compounds having an average of at least two epoxide groups per molecule; and (b) a cyanamide of organic primary amine or mixture of cyanamides of organic primary amines having an average of more than one cyanamide moiety per molecule; wherein one mole of cyanamide is employed to cure 0.1 to 4.0 moles of epoxide.
Claim 3
Dependent Claim
118 words
A composition of claim 1 wherein the 1,2 epoxide compound is selected from the group consisting of compounds of the formula ##STR6## where R 4 and R 5 independently are alkyl groups containing 1 to 8 carbon atoms, or together form a 5 or 6 member cycloaliphatic group; compounds of the formula ##STR7## where R 6 and R 7 independently are alkyl groups containing 1 to 8 carbon atoms or together form a 5 or 6 membered cycloaliphatic group, and R 8 is a hydrogen atom or a methyl group; glycidyl ethers of polynuclear phenols, and of novolaks formed from formaldehyde and phenol or cresol; cycloaliphatic epoxides containing non-terminal epoxide groups; and glycidyl amines of polynuclear aromatic amines.
Claim 4
Dependent Claim
86 words
A composition according to claim 1 wherein the cyanamide of an organic primary amine is of the following formula R.sup.3 (NHCN).sub.n wherein n is an integer of the group 1 to 10 and R 3 is an n-valent organic radical from the series of aliphatic of 2 to 12 carbon atoms, cycloaliphatic of 4 to 6 carbon atoms, aromatic of 6 to 30 carbon atoms, or a 5 or 6 membered heterocyclic containing carbon atoms and heteroatoms of the group consisting of oxygen, sulfur, and nitrogen.
Claim 5
Dependent Claim
18 words
A composition of claim 3 wherein R 3 is alkylene containing 6 carbon atoms and n is two.
Claim 6
Dependent Claim
14 words
A composition of claim 3 wherein R 3 is m-xylylene and n is two.
Claim 7
Dependent Claim
14 words
A composition of claim 3 wherein R 3 is 4,4'-methylenebis(phenyl) and n is two.
Claim 8
Dependent Claim
15 words
A composition of claim 3 wherein ##STR8## where m averages one and n averages three.
Claim 9
Dependent Claim
32 words
A composition of claims 6 or 7 wherein the 1,2 epoxide compound is selected from the group consisting of 1,3-diglycidyl-5-sec-amyl-5-ethylhydantoin, a mixture of 1,3-diglycidyl-5,5-dimethylhydantoin and 1-glycidyl-3-(2-glycidyloxypropyl)-5,5-dimethylhydantoin, diglycidylether of 2,2-bis(4-hydroxyphenyl)propane, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate and tetraglycidyl-bis(4-aminophenyl)methane.
Claim 10
Dependent Claim
26 words
A composition of claim 3 wherein R 3 is ##STR9## n is two and X is hydrogen, alkyl, aryl, dialkylamino, diacylamino group, or the group --NHCN.
Claim 11
Dependent Claim
50 words
A composition of claim 9 wherein X is hydrogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 12 carbon atoms, diloweralkylamino, diarylamino wherein said lower alkyl group contains 1 to 6 carbon atoms and said aryl group contains 6 to 12 carbon atoms or the group --NHCN.
Claim 12
Dependent Claim
11 words
A composition of claim 10 wherein X is phenyl or diphenylamino.
Claim 13
Dependent Claim
22 words
A composition of claim 1 which further comprises an epoxide curing agent selected from the group of aromatic amines or phenolic hardeners.
Claim 14
Dependent Claim
31 words
A composition of claims 1 or 12 which further comprises from 0.1 to 10 percent by weight of the combined weights of epoxide resin and curing agent of a curing accelerator.
Claim 15
Dependent Claim
21 words
A composition according to claim 1 wherein one mole of cyanamide is employed to cure 1.0 to 2.0 moles of epoxide.
Claim 16
Dependent Claim
13 words
A composition according to claim 1 which further comprises an inert organic solvent.
References Cited (Backward Citations)
US3893974A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-09-17 | 1983-03-19 | 1983-09-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-17 | 1987-03-19 | 1987-09-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-17 | 1991-03-19 | 1991-09-18 | $7700.00 | Window Closed / Lapsed |