Curing of polyglycidyl ether resins
AssigneeThe General Tire & Rubber Company
InventorsDavid R. Sponseller, Earl G. Melby, Hubert J. Fabris
Life of this patent
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Abstract
Cyanoethylated and/or cyanopropylated hydrazides are useful as curing agents for polyglycidyl ether resins. These hydrazide-epoxy resin mixtures have useful pot lives and exhibit fast cures.
Claims28
The method which comprises reacting in aqueous media at least a sufficient amount of at least one nitrile selected from the group consisting of acrylonitrile and methacrylonitrile with at least one hydrazide selected from the group consisting of ##STR9## where R is a hydrocarbon radical having from 1 to 30 carbon atoms and where m is a number from 2 to 6 and ##STR10## where R' is a hydrocarbon moiety selected from the group consisting of dimers, trimers, oligomers, polymers and copolymers having an average molecular weight of from about 250 to 5000 and which may contain a minor amount by weight of --C.tbd.N groups and where n is a number from 2 to 10, at a temperature of from about 20.degree. to 100.degree. C. and for a period of time to form at least one compound selected from the group consisting of ##STR11## where R is a hydrocarbon radical having from 1 to 30 carbon atoms and where m is a number from 2 to 6 and ##STR12## where R' is a hydrocarbon moiety selected from the group-consisting of dimers, trimers, oligomers, polymers and copolymers having an average molecular weight of from 250 to 5000 and which may contain a minor amount by weight of --C.tbd.N groups and where n is a number from 2 to 10 and and where R" is hydrogen or methyl.
A compound selected from the group consisting of ##STR13## where R is a hydrocarbon radical of from 1 to 30 carbon atoms and where m is a number from 2 to 6 and ##STR14## where R' is a hydrocarbon moiety selected from the group consisting of dimers, trimers, oligomers, polymers and copolymers having an average molecular weight of from about 250 to 5000 and which may contain a minor amount by weight of --C.tbd.N groups and where n is a number from 2 to 10 and where R" is hydrogen or methyl and mixtures of such compounds.
Biscyanoethyl carbohydrazide.
A curable composition comprising
- (I.) at least one polyglycidyl ether resin having an average of at least two glycidyl ether groups, an epoxide equivalent of from about 130 to 6000 and a molecular weight of from about 300 to 12,000 and
- (II.) at least one hydrazide compound selected from group consisting of ##STR15## where R is a hydrocarbon radical of from 1 to 30 carbon atoms and where m is a number from 2 to 6 and ##STR16## where R' is a hydrocarbon moiety selected from the group consisting of dimers, trimers, oligomers, polymers and copolymers having an average molecular weight of from about 250 to 5000 and which may contain a minor amount by weight of --C.tbd.N groups and where n is a number from 2 to 10 and where R" is hydrogen or methyl, the equivalent ratio of epoxy ##STR17## of (I.) to amine (--NH--) of (II.) being from about 1:1 to 12:1, or from about 1:1 to 6:1.
The method which comprises mixing and heating at a temperature of from about 100.degree. to 165.degree. C., or from about 120.degree. 150.degree. C., for a period of time sufficient to cause curing of
- (I.) at least one polyglycidyl ether resin having an average of at least two glycidyl ether groups, an epoxide equivalent of from about 130 to 6000 and a molecular weight of from about 300 to 12,000 and
- (II.) at least one hydrazide compound selected from group consisting of ##STR18## where R is a hydrocarbon radical of from 1 to 30 carbon atoms and where m is a number from 2 to 6 and ##STR19## where R' is a hydrocarbon moiety selected from the group consisting of dimers, trimers, oligomers, polymers and copolymers having an average molecular weight of from about 250 to 5000 and which may contain a minor amount by weight of --C.tbd.N groups and where n is a number from 2 to 10 and where R" is hydrogen or methyl, the equivalent ratio of epoxy ##STR20## of (I.) to amine (--NH--) of (II.) being about 1:1 to 12:1, or from about 1:1 to 6:1.
Dependencies are inferred from the claim text.