Unitary curable resin compositions

Claim 2

A curing agent suitable for use with epoxy resin systems comprising the solid thermoplastic reaction product of an epoxy resin containing a plurality of oxirane groups and an imidazole compound selected from ##STR13## wherein R is hydrogen, alkyl, alkenyl, aryl, or halo; ##STR14## wherein R is defined as above; ##STR15## wherein R is defined as above and R 1 is alkyl, alkenyl, aryl, or halo; and d. mixtures of such compounds, the ratio of oxirane groups in the epoxy resin to the molecules of imidazole compound being between 1:1 and 2:1, said reaction product having a melting point from about 70° C. to about 140° C.

Claim 3

A curing agent suitable for use with epoxy resin systems comprising a solid thermoplastic reaction product of (1) an epoxy resin containing a plurality of oxirane groups and (2) an imidazole compound selected from ##STR16## wherein R is hydrogen, alkyl, alkenyl, aryl or halo; ##STR17## wherein R is defined as above; ##STR18## wherein R is defined as above and R 1 is alkyl, alkenyl, aryl or halo; d. mixtures of such compounds, and (3) a polyfunctional proton-donor compound selected from the group consisting of polycarboxylic acids and phenolic novolac resins, the ratio of oxirane groups in the epoxy resin to the molecules of imidazole compound being between 0.8:1 and 2.2:1 and the ratio of acid equivalents of proton-donor compound to molecules of imidazole compound being up to 1.5:1, said epoxy resin having an epoxide equivalent weight from about 170 to about 2000, said reaction product having a melting point from about 70° C. to about 140° C.

Claim 4

A curing agent suitable for use with epoxy resin systems comprising a solid thermoplastic reaction product of (1) an epoxy resin containing a plurality of oxirane groups and (2) an imidazole compound selected from ##STR16## wherein R is hydrogen, alkyl, alkenyl, aryl or halo; ##STR17## wherein R is defined as above; ##STR18## wherein R is defined as above and R 1 is alkyl, alkenyl, aryl or halo; d. mixtures of such compounds, and (3) a polyfunctional proton-donor compound selected from the group consisting of polycarboxylic acids and phenolic novolac resins, the ratio of oxirane groups in the epoxy resin to the molecules of imidazole compound being between 0.8:1 and 2.2:1 and the ratio of acid equivalents of proton-donor compound to molecules of imidazole compound being up to 1.5:1, said epoxy resin having an epoxide equivalent weight from about 170 to about 2000, said reaction product having a melting point from about 70° C. to about 140° C.

Claim 5

The curing agent defined in claim 1 wherein the imidazole compound is selected from ##STR19## wherein R is hydrogen, alkyl, or phenyl and the cumulative total of all carbon atoms in the R groups is from 1 to 8; ##STR20## wherein R is hydrogen, alkyl or phenyl and the cumulative total of all carbon atoms in the R groups is from 1 to 8; ##STR21## wherein R is hydrogen, alkyl or phenyl and R 1 is alkyl or phenyl and the cumulative total of all carbon atoms in the R and R 1 groups is from 1 to 8; and d. mixtures of such compounds.

Claim 6

The curing agent as defined in claim 3 wherein the imidazole compound is 2-ethyl, 4-methyl imidazole; 2-methyl imidazole, 2-phenyl-2-imidazoline, benzimidazole, or mixtures thereof.

Claim 7

The curing agent as defined in claim 1 wherein said epoxy resin has an epoxide equivalent weight from about 170 to about 2000.

Claim 8

The curing agent as defined in claim 1 wherein said epoxy resin is a diglycioyl ether formed of bisphenol A and epichlorohydrin or a glycidated novolac formed of epichlorohydrin and a phenolic novolac resin.

Claim 9

The curing agent as defined in claim 2 wherein the imidazole compound is selected from ##STR22## wherein R is hydrogen, alkyl, or phenyl and the cumulative total of all carbon atoms in the R groups is from 1 to 8; ##STR23## wherein R is hydrogen, alkyl or phenyl and the cumulative total of all carbon atoms in the R groups is from 1 to 8; ##STR24## wherein R is hydrogen, alkyl or phenyl and R 1 is alkyl or phenyl and the cumulative total of all carbon atoms in the R and R 1 groups is from 1 to 8; and d. mixtures of such compounds.

Claim 10

The curing agent as defined in claim 2 wherein the imidazole compound is 2-ethyl, 4-methyl imidazole; 2-methyl imidazole, 2-phenyl-2-imidazoline, benzimidazole, or mixtures thereof.

Claim 11

The curing agent as defined in claim 2 wherein said epoxy resin is a diglycidyl ether formed of bisphenol A and epichlorohydrin or a glycidated novolac formed of epichlorohydrin and a phenolic novolac resin.

Claim 12

The curing agent of claim 2 wherein said polyfunctional proton-donor compound is an acid selected from the group consisting of chlorendic acid, maleic acid or itaconic acid, acids of the formula HOOC-(CH 2 ) n -COOH, and aromatic dibasic acids.

Claim 13

The curing agent as defined in claim 3 wherein said epoxy resin has an epoxide equivalent weight from about 170 to about 2000.

Claim 14

Curable epoxy resin compositions comprising, as a curing agent therein, an effective quantity of the thermoplastic curing agent as defined in claim 1.

Claim 15

Curable epoxy resin compositions, comprising as a curing agent therein, an effective quantity of the thermoplastic curing agent as defined in claim 2.

Claim 16

Curable epoxy resin compositions, comprising as a curing agent therein, an effective quantity of the thermoplastic curing agent as defined in claim 5.

Claim 17

Curable epoxy resin compositions, comprising as a curing agent therein, an effective quantity of the thermoplastic curing agent as defined in claim 7.

Claim 18

Curable epoxy resin compositions as defined in claim 12 comprising, in addition to the thermoplastic curing agent therein, dicyandiamid in an amount up to 25 times the weight of said curing agent or an organic carboxylic acid anhydride in an amount to provide up to 1.425 anhydride equivalents for each epoxide equivalent of total epoxy resin.

Claim 19

Curable epoxy resin compositions as defined in claim 13 comprising, in addition to the thermoplastic curing agent therein, dicyandiamid in an amount up to 25 times the weight of said curing agent or an organic carboxylic acid anhydride in an amount to provide up to 1.425 anhydride equivalents for each epoxide equivalent of total epoxy resin.

Claim 20

Curable epoxy resin compositions as defined in claim 12 comprising, in addition to the thermoplastic curing agent therein, dicyandiamid in an amount from 0.04 to 25 times the weight of said curing agent.

Claim 21

Curable epoxy resin compositions as defined in claim 13 comprising, in addition to the thermoplastic curing agent therein, dicyandiamid in an amount from 0.04 to 25 times the weight of said curing agent.

Claim 22

An article of manufacture suitable for use as a sheet adhesive comprising an inert tape and an epoxy resin adhesive composition comprising a curing agent as defined in claim 2.

Claim 23

An article of manufacture suitable for use as a sheet adhesive comprising an inert tape and an epoxy resin adhesive composition comprising a curing agent as defined in claim 1.

Claim 24

An article of manufacture suitable for use as a sheet adhesive comprising an inert tape and an epoxy resin adhesive composition comprising a curing agent as defined in claim 8.

Claim 25

A process for converting a polyepoxide having more than one vicinal epoxy group per molecule into an insoluble, infusible product which comprises heating said polyepoxide at an elevated temperature with a curing amount of a combination comprising (1) a fusible, ketone-soluble adduct prepared by reacting (a) an epoxy compound containing at least two vicinal epoxy groups with (b) an imidazole compound of the general formula: ##STR25## wherein each R is hydrogen or a hydrocarbon radical selected from the group consisting of alkyl and cycloalkyl radicals of up to 12 carbon atoms and aryl radicals, at a temperature from about 50° to 250° C. and for a time sufficient to complete the reaction, said epoxy compound and imidazole compound being employed in amounts to furnish from 0.8 to 2.2 epoxy groups per secondary amino group and (2) an epoxy co-curing agent selected from the group consisting of at least one carboxylic acid anhydride and dicyandiamide.

Claim 26

A process for converting a polyepoxide having more than one vicinal epoxy group per molecule into an insoluble, infusible product which comprises heating said polyepoxide at an elevated temperature with a curing amount of a combination comprising (1) a fusible, ketone-soluble adduct prepared by reacting (a) an epoxy compound containing at least two vicinal epoxy groups with (b) an imidazole compound of the general formula: ##STR25## wherein each R is hydrogen or a hydrocarbon radical selected from the group consisting of alkyl and cycloalkyl radicals of up to 12 carbon atoms and aryl radicals, at a temperature from about 50° to 250° C. and for a time sufficient to complete the reaction, said epoxy compound and imidazole compound being employed in amounts to furnish from 0.8 to 2.2 epoxy groups per secondary amino group and (2) an epoxy co-curing agent selected from the group consisting of at least one carboxylic acid anhydride and dicyandiamide.

Claim 27

A process as in claim 23 wherein the adduct is prepared from a polyglycidyl ether of 2,2-bis(4-hydroxyphenyl) propane.

Claim 28

A process as in claim 23 wherein the co-curing agent is at least one polycarboxylic acid anhydride.

Claim 29

A process as in claim 23 wherein the co-curing agent is dicyandiamide.

Claim 30

A shelf-stable, heat-curable composition comprising (A) a polyepoxide having more than one vicinal epoxy group per molecule and a curing amount of (B) a combination comprising (1) a fusible, ketone-soluble adduct prepared by reacting (a) an epoxy compound containing at least two vicinal epoxy groups with (b) an imidazole compound of the general formula: ##STR26## wherein each R is hydrogen or a hydrocarbon radical selected from the group consisting of alkyl and cycloalkyl radicals of up to 12 carbon atoms and aryl radicals, at a temperature from about 50° to 250° C and for a time sufficient to complete the reaction, said epoxy compound and imidazole compound being employed in amounts to furnish from 0.8 to 2.2 epoxy groups per secondary amino groups, and (2) an epoxy co-curing agent selected from the group consisting of at least one carboxylic acid anhydride and dicyandiamide.

Claim 31

A shelf-stable, heat-curable composition comprising (A) a polyepoxide having more than one vicinal epoxy group per molecule and a curing amount of (B) a combination comprising (1) a fusible, ketone-soluble adduct prepared by reacting (a) an epoxy compound containing at least two vicinal epoxy groups with (b) an imidazole compound of the general formula: ##STR26## wherein each R is hydrogen or a hydrocarbon radical selected from the group consisting of alkyl and cycloalkyl radicals of up to 12 carbon atoms and aryl radicals, at a temperature from about 50° to 250° C and for a time sufficient to complete the reaction, said epoxy compound and imidazole compound being employed in amounts to furnish from 0.8 to 2.2 epoxy groups per secondary amino groups, and (2) an epoxy co-curing agent selected from the group consisting of at least one carboxylic acid anhydride and dicyandiamide.

Claim 32

A composition as in claim 27 wherein the imidazole adduct is employed in amounts from about 1% to 20% by weight of the polyepoxide.

Claim 33

A composition as in claim 27 wherein the adduct is prepared by reacting a polyglycidyl ether of 2,2-bis(4-hydroxyphenyl) propane having an average molecular weight of from about 350 to 400 with 2-methylimidazole.

Claim 34

A composition as in claim 27 wherein the co-curing agent comprises at least one carboxylic acid anhydride.

Claim 35

A composition as in claim 27 wherein the co-curing agent is dicyandiamide.