Moisture resistant, wet winding epoxy resin system containing aromatic diamines

Claim 2

A curable, thermosetting resin composition consisting essentially of: (a) at least one cycloaliphatic epoxy resin containing at least two 1,2-epoxy groups per molecule: (b) at least one aromatic diamine hardener in an amount sufficient to provide from about 0.4 to about 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy group in the epoxy resin, said diamine hardener having the following formula: ##STR10## wherein Ar represents a single or fused aromatic nucleus of up to 10 carbon atoms, which optionally may contain one or more R and R 1 substituents; X represents O, S, ##STR11## or a single bond; R and R 1 individually represent alkyl of from 1-12 carbon atoms or halogen groups; R 2 represents hydrogen or an alkyl group of from 1-12 carbon atoms; and n has a value of from 0 to 4; and wherein (a) and (b) have a viscosity as measured at 25° C. of no greater than 2000 cps; and (c) a structural fiber.

Claim 3

The curable composition of claim 1 wherein the aromatic diamine hardener of the indicated formula is the sole diamine hardener present in the epoxy resin composition.

Claim 4

The curable composition of claim 1 wherein the cycloaliphatic epoxy resin is present in an amount such that the viscosity of said composition is less than about 2000 cps.

Claim 5

The curable composition of claim 2 wherein Ar of the aromatic diamine hardener is phenylene.

Claim 6

The curable composition of claim 2 wherein Ar of phenylene, R represents halogen, and X is isopropylidene.

Claim 7

The curable composition of claim 2 wherein the aromatic diamine hardener is: ##STR12##

Claim 8

The curable composition of claim 1 wherein the aromatic diamine hardener is: ##STR13##

Claim 9

The curable composition of claim 1 wherein the aromatic diamine hardener is: ##STR14##

Claim 10

The curable composition of claim 1 wherein the aromatic diamine hardener is: ##STR15##

Claim 11

The curable composition of claim 1 wherein the aromatic diamine hardener is: ##STR16##

Claim 12

The composition of claim 1, wherein the cycloaliphaic epoxide is bis(2,3-epoxycyclopentyl) ether.

Claim 13

The composition of claim 1, wherein the cycloaliphatic epoxide is vinylcyclohexene diepoxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane meta-dioxane, 3,4-epoxycyclohexyl-methyl 3,4-epoxycyclohexane carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, bis(3,4-epoxy)cyclohexylmethyl) adipate or mixtures thereof.

Claim 14

The composition of claim 1, further comprising up to 40 percent by weight of a coepoxy resin.

Claim 15

The composition of claim 13, wherein the coepoxy resin is selected from one or more of the following: ##STR17## wherein n is from 0 to about 15; ##STR18## wherein n is from 0.1 to about 8 and R is hydrogen; and ##STR19## wherein n is from 0.1 to about 8 and R is CH 3 .

Claim 16

The composition of claim 1, further comprising up to 35% by weight of a modifier which increases the modulus of the epoxy resin.

Claim 17

The composition of claim 1 wherein said structural fiber has a tensile strength of greater than about 1,000,000 psi, a tensile modulus of greater than about two million psi, and a decomposition temperature of greater than about 200° C.

Claim 18

The composition of claim 16, wherein said structural fiber is selected from the group consisting of from carbon, graphite, glass, silicon carbide, poly[benzothiazole), poly(benzimidazole), poly(benzoxazole), alumina, titania, boron, aromatic polyamides, and mixtures thereof.

Claim 19

The composition of claim 1 in the form of a composite.

Claim 20

A composite material consisting essentially of: (a) a cycloaliphatic epoxide resin containing at least two 1,2-epoxy groups per molecule; (b) at least one aromatic diamine hardener in an amount sufficient to provide from about 0.4 to about 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy group in the epoxy resin, said diamine hardener having the following formula: ##STR20## wherein Ar represents a single or fused aromatic nucleus of up to 10 carbon atoms, which optionally may contain one or more R and R 1 substituents; X represents O, S, ##STR21## or a single bond; R and R 1 individually represent alkyl of from 1-12 carbon atoms or halogen groups; R 2 represents hydrogen or an alkyl group of from 1-12 carbon atoms; and n has a value of from 0 to 4; and wherein (a) and (b) have a viscosity as measured at 25° C. of no greater than 2000 cps. (c) an aromatic trihydroxy cure accelerator selected from the group consisting of phloroglucinol, n-propyl gallate, pyrogallol and mixtures thereof in an amount sufficient to provide from about 0.01 to about 0.34 equivalents of hydroxy per equivalent of 1,2-epoxy group in the epoxide resin; and (d) up to about 85% by weight, based on the total weight of the composition, of a structural fiber having a tensile strength of greater than about 100,000 psi, a tensile modulus of greater than about two million psi, and a decomposition temperature of greater than about 200° C.

Claim 21

A composite material consisting essentially of: (a) a cycloaliphatic epoxide resin containing at least two 1,2-epoxy groups per molecule; (b) at least one aromatic diamine hardener in an amount sufficient to provide from about 0.4 to about 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy group in the epoxy resin, said diamine hardener having the following formula: ##STR20## wherein Ar represents a single or fused aromatic nucleus of up to 10 carbon atoms, which optionally may contain one or more R and R 1 substituents; X represents O, S, ##STR21## or a single bond; R and R 1 individually represent alkyl of from 1-12 carbon atoms or halogen groups; R 2 represents hydrogen or an alkyl group of from 1-12 carbon atoms; and n has a value of from 0 to 4; and wherein (a) and (b) have a viscosity as measured at 25° C. of no greater than 2000 cps. (c) an aromatic trihydroxy cure accelerator selected from the group consisting of phloroglucinol, n-propyl gallate, pyrogallol and mixtures thereof in an amount sufficient to provide from about 0.01 to about 0.34 equivalents of hydroxy per equivalent of 1,2-epoxy group in the epoxide resin; and (d) up to about 85% by weight, based on the total weight of the composition, of a structural fiber having a tensile strength of greater than about 100,000 psi, a tensile modulus of greater than about two million psi, and a decomposition temperature of greater than about 200° C.

Claim 22

The composite of claim 19, wherein the cycloaliphatic epoxide is bis(2,3-epoxycyclopentyl) ether.

Claim 23

The composite of claim 19, wherein the cycloaliphatic epoxide is vinylcyclohexene diepoxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane meta-dioxane, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, bis(3,4-epoxycyclohexylmethyl) adipate or mixtures thereof.

Claim 24

The composite of claim 19, further comprising up to about 30 percent by weight of a coepoxy resin, based on the combined weight of the cycloaliphatic epoxide resin and the coepoxy resin.