Polymeric resins derived from 1-oxa-3-aza tetraline group-containing compounds and cycloaliphatic epoxides

Abstract

A composition comprising a polymeric resin derived from (A) at least one compound containing an average of more than one 1-oxa-3-aza-tetraline group per molecule with (B) at least one cycloaliphatic epoxide containing at least two epoxide groups, at least one of said epoxide groups being part of said ring, the mole ratio of (B) to (A) being in the range of about 0.2 to about 2.

I claim: 
     
       1. A composition comprising a polymeric resin derived from (A) at least one compound containing an average of more than one 1-oxa-3-aza-tetraline group per molecule .[.with.]. .Iadd.and/or the prepolymers thereof with .Iaddend.   (B) at least one cycloaliphatic epoxide containing at least two epoxide groups, at least one of said epoxide groups being part of said ring, the .[.mole.]. ratio of .[.(B) to (A).]. .Iadd.epoxide groups to 1-oxa-3-aza-tetraline groups .Iaddend.being in the range of about 0.2 to about 2.   
     
     
       2. The composition of claim 1 wherein component (B) has at least one epoxide group directly attached to said ring. 
     
     
       3. The composition according to claim 1, wherein said 1-oxa-3-aza-tetraline groups include an aromatic substituent at the nitrogen atom. 
     
     
       4. The composition of claim 1 wherein component (A) is the reaction product of at least one amine, at least one phenol, and formaldehyde. 
     
     
       5. The composition of claim 4 wherein said phenol is selected from the group consisting of phenol, m- and p-cresol, m- and p-ethyl-phenol, m- and p-isopropylphenol, m- and p-methoxy-phenol, m- and p-ethoxyphenol, m- and p-isopropyloxy-phenol, m- and p-chlorophenol and B-naphthol. 
     
     
       6. The composition of claim 4 wherein said phenol is selected from the group consisting of 4,4'-dihydroxydiphenylmethane, 3,3'-dihydroxy-diphenylmethane, 2,2-bis-(4-hydroxy-phenyl)-propane, 4,4'-dihydroxystilbene, hydroquinone, pyrocatechin and resorcin. 
     
     
       7. The composition of claim 4 wherein said amine is selected from the group consisting of aniline, o-, m- and p-phenylene diamine, benzidine, 4,4'-diaminodiphenyl methane, and 2,2-bis-(aminophenyl)propane. 
     
     
       8. The composition of claim 1 wherein component (A) is .Iadd.derived from .Iaddend.a Novolak resin. 
     
     
       9. The composition of claim 1 wherein component (B) has an equivalent weight in the range of about 70 to about 250. 
     
     
       10. The composition of claim 1 wherein component (B) has an equivalent weight in the range of about 120 to about 200. 
     
     
       11. The composition of claim 1 wherein component (B) is selected from the group consisting of 2-(3,4-epoxy)cyclohexyl-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane, 1 to 4 times methylated 2-(3,4-epoxy)cyclohexyl-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane, 4-(1,2-epoxyethyl)-1,2-epoxycyclohexane, .[.1,2,8,9-diepoxy-p-methane, 2,2-bis(3,4-epoxycyclohexyl)propane.]., .Iadd.1,2,8,9-diepoxy-p-menthane, 2,2-bis(3,4-epoxycyclohexyl)propane .Iaddend.bis-(2,3-epoxycyclopentyl)ether, 1,2,5,6-diepoxy-4,7-hexahydromethanoindane, bis-(3,4-epoxy-cyclohexylmethyl)adipate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, bis(3,4-epoxy-cyclohexylmethyl)terephthalate, bis(3,4-epoxy-6-methyl-cyclohexylmethyl)-terephthalate,3,4-epoxy-cyclohexane carboxylic acid-(3,4-epoxy-cyclohexylmethyl)ester, 3,4-epoxy-6-methylcyclohexanecarboxylic acid-(3,4-epoxy-6-methylcyclohexylmethyl)ester, 1,2-bis-(5(1,2-epoxy)-4,7-hexahydromethanoindaneoxy)-ethane, .[.1,1,1-tris((5-(1,2-epoxy)-4,7-hexahydromethynoindaneoxy)-methyl)-propane.]. .Iadd.1,1,1-tris((5-(1,2-epoxy)-4,7-hexahydromethanoindaneoxy)-methyl)propane .Iaddend.and 4,5-epoxyhexahydrophthalic acid-bis-(3,4-epoxycyclohexylmethyl)ester. 
     
     
       12. The composition of claim 1 wherein component (B) is selected from the group consisting of 2-(3,4-epoxy)cyclohexyl-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane, 1 to 4 times methylated 2-(3,4-epoxy)cyclohexyl-5,5-spiro(3,4-epoxy)cyclohexane-m-dioxane, bis(3,4-epoxy-cyclohexylmethyl)adipate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, 3,4-epoxy-cyclohexane-carboxylic acid-(3,4-epoxy-cyclohexylmethyl)ester and 3,4-epoxy-6-methylcyclohexane carboxylic acid-(3,4-epoxy-6-methylcyclohexylmethyl)ester. 
     
     
       13. The composition of claim 1 wherein component (B) is represented by the formula   X--Y     wherein:   X is a 3,4-epoxycyclohexyl group or a mono- or dimethyl substituted 3,4-epoxycyclohexyl group; and   Y is a group represented by the formula ##STR13## wherein n is a number in the range of from zero to 2, or a group represented by the formula ##STR14## or a group represented by the formulae   --COO--CH.sub.2 --X     or     --CH.sub.2 --Z--CH.sub.2 --X     wherein:     X is as defined above, and Z is .[.derived from.]. .Iadd.the acid radical of .Iaddend.an aliphatic, cycloaliphatic or aromatic dicarboxylic acid group.   
     
     
       14. The composition of claim 1 wherein .[.the.]. .Iadd.said .Iaddend.mole ratio .[.of (B) to (A).]. is in the range of from about 0.8 to about 1.5. 
     
     
       15. The composition of claim 1 wherein components (A) and (B) are reacted at a temperature in the range of about 50° C. to about 300° C. 
     
     
       16. The composition of claim 1 wherein components (A) and (B) are reacted at a temperature in the range of about 100° C. to about 250° C. 
     
     
       17. The composition of claim 1 wherein components (A) and (B) are reacted at a temperature in the range of about 140° C. to about 230° C. 
     
     
       18. The composition of claim 1 wherein components (A) and (B) are reacted in the presence of an effective amount of catalyst to accelerate the reaction.