Heterocyclic multifunctional amine adducts and curable compositions containing the same

Claim 2

A curable composition comprising: (A) an epoxy resin; and (B) a heterocyclic compound having the formula: ##STR70## wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, alkyl, phenyl, ##STR71## and R 5 and R 6 may jointly form ##STR72## and R 7 is selected from the group consisting of ##STR73##

Claim 3

The curable composition according to claim 1, wherein the heterocyclic compound is the reaction product of at least one aromatic or aliphatic polyamine compound having at least two primary amine groups, which are separated by no more than one carbon atom, with at least one carbonyl-containing compound selected from the group consisting of aldehydes and ketones, wherein said polyamine is selected from: aliphatic polyamines having 2-20 carbon atoms corresponding to the formula: ##STR74## wherein A is a direct carbon-carbon bond or --CH 2 -- and R 3 and R 4 are each independently hydrogen or alkyl which may be branched or unbranched and which may be unsubstituted or substituted with amine groups; ##STR75## wherein said aldehydes correspond to the formula: ##STR76## wherein R represents alkyl of 1-20 carbon atoms, which may be branched or unbranched, and which may be unsubstituted or substituted with --CHO or --COOH; --CHO; --COOH; or phenyl which may be unsubstituted or substituted with --CHO, --OH or lower alkoxy of 1-5 carbon atoms, and wherein said ketones correspond to the formula: ##STR77## wherein R 1 and R 2 each independently represent alkyl of 1-20 carbon atoms, which may be branched or unbranched, and whose chain may be interrupted by one or more ##STR78## groups; phenyl; or R 1 and R 2 may together form a cycloaliphatic ring which may be interrupted by ##STR79## group; or R 1 and R 2 may together form an O -heterocyclic ring which may be substituted with lower alkyl of 1-5 carbon atoms, --OH or acetyl.

Claim 4

The curable composition according to claim 2 wherein the heterocyclic compound is formed in situ.

Claim 5

The curable composition of claim 2 wherein the heterocyclic compound is formed by reacting the polyamine and the carbonyl-containing compound in stoichiometric proportions.

Claim 6

The curable composition according to claim 1, wherein said epoxy resin is N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenyl methane.

Claim 7

The curable composition according to claim 2, wherein the polyamine compound is selected from the group consisting of: 1,2-diamino-benzene; 1,8-diamino-naphthalene;

Claim 8

3-diamino-propane; 3,3',4,4'-tetra amino-diphenyl methane; 1,2,4,5-tetra amino-benzene; and 1,4,5,8-tetra amino-napthanlene.

Claim 9

3-diamino-propane; 3,3',4,4'-tetra amino-diphenyl methane; 1,2,4,5-tetra amino-benzene; and 1,4,5,8-tetra amino-napthanlene.

Claim 10

The curable composition according to claim 2, wherein the aldehyde is selected from the group consisting of terephthalaldehyde; glyoxal, glutaraldehyde; glyoxylic acid; salicylaldehyde; vanillin and σ-vanillin.

Claim 11

The curable composition according to claim 2, wherein the ketone is selected from the group comprising: 2,4-pentanedione; 2,3-butanedione; benzil; 1,3-cyclohexane-dione; acetone; 2-butanone; 2-heptanone; dehydroacetic acid; and acetophenone.

Claim 12

The curable composition according to claim 6, wherein the polyamine is 1,8-diamino-naphthalene.

Claim 13

The curable composition according to claim 6, wherein the polyamine is 1,3-diamino-propane.

Claim 14

The curable composition according to claim 7, wherein the aldehyde is terephthalaldehyde.

Claim 15

The curable composition according to claim 8, wherein the ketone is acetone.

Claim 16

The curable composition according to claim 8, wherein the ketone is 2,4-pentanedione.

Claim 17

The curable composition according to claim 2, which further comprises a reinforcing agent selected from the group consisting of cotton, paper, glass fiber, polyester fiber, polyaramid fiber, polyolefin fiber, graphite fiber and metal fiber.

Claim 18

The curable composition according to claim 14, wherein the reinforcing agent is graphite fiber.

Claim 19

The curable composition according to claim 15, wherein the graphite fiber forms a woven fabric.

Claim 20

The curable composition according to claim 14, which further comprises a surfactant.

Claim 21

The curable composition according to claim 14, which further comprises a thixotrope.

Claim 22

The curable composition according to claim 14, which further comprises a catalyst.

Claim 23

The curable composition according to claim 14, which further comprises an elastomer.

Claim 24

The curable composition according to claim 14, which further comprises a hardener.

Claim 25

A method of curing the curable composition according to claim 2, wherein the curable composition is subjected to sufficient energy to cause cross-linking.

Claim 26

The method of curing according claim 21, wherein the composition is heated.

Claim 27

The method of curing according to claim 21, wherein the composition is subjected to microwave radiation.

Claim 28

The curable composition according to claim 14, wherein the reinforcing agent is formed into laminae.

Claim 29

The composite article formed by curing the composition according to claim 25.