Thermosettable compositions and thermosets therefrom

1. A thermosettable epoxy resin composition comprising

(A) a residual oligomeric product; wherein the residual oligomeric product comprises a polyfunctional aliphatic or cycloaliphatic epoxy resin which has been isolated from an epoxy resin product formed as a result of an epoxidation process comprising the reaction of

(i) an aliphatic or cycloaliphatic hydroxyl-containing material;

(ii) an epihalohydrin;

(iii) a basic-acting substance;

(iv) a non-Lewis acid catalyst; and

(v) optionally, one or more solvents;

(B) an epoxy curing material comprising

(i) an epoxy resin curing agent;

(ii) an epoxy resin curing catalyst; or

(iii) both (i) and (ii); and

(C) optionally, an epoxy resin compound other than the polyfunctional aliphatic or cycloaliphatic epoxy resin (A).

2. The composition of claim 1 wherein the aliphatic or cycloaliphatic hydroxyl containing material is selected from the group consisting of cyclohexanedialkanols; cyclohexenedialkanols; cyclohexanolmonoalkanols; cyclohexenolmonoalkanols; decahydronaphthalenedialkanols; octahydronaphthalenedialkanols; 1,2,3,4-tetrahydronaphthalenedialkanols; and bridged cyclohexanols.

3. The composition of claim 2 wherein the aliphatic or cycloaliphatic hydroxyl containing material is selected from the group consisting of cyclohexanedialkanols and cyclohexenedialkanols.

4. The composition of claim 2 wherein the aliphatic or cycloaliphatic hydroxyl containing material is selected from the group consisting of cis-, trans-1,3- and 1,4-cyclohexanedimethanol; cis-, trans-1,2-cyclohexanedimethanol; cis-, trans-1,3-cyclohexanedimethanol; cis-, trans-1,4-cyclohexanedimethanol; a methyl substituted cyclohexanedimethanol; 1,1-cyclohexanedimethanol; a cyclohexenedimethanol; 3-cyclohexene-1,1-dimethanol, 6-methyl-; 4,6-dimethyl-3-cyclohexene-1,1-dimethanol; cyclohex-2-ene-1,1-dimethanol; 1,1-cyclohexanediethanol; 1,4-bis(2-hydroxyethoxy)cyclohexane; 1,4-cyclohexanediethanol; 1,4-(2-hydroxyethyloxy)cyclohexane; and 1,4-(2-hydroxyethyloxy)cyclohex-2-ene.

5. The composition of claim 1 wherein the cycloaliphatic hydroxyl containing material comprises a material selected from the group consisting of cycloaliphatic diols, polycycloaliphatic diols, monol monoalkanols and dialkanols.

6. The composition of claim 1 wherein the aliphatic hydroxyl containing material comprises a material selected from the group consisting of alkoxylated phenolic reactants; alkoxylation products of the hydrogenated aromatic phenolic reactants; neopentyl glycol; trimethylol propane; ethylene glycol; propylene glycol; triethylene glycol; higher alkoxylated ethylene glycols; pentaerythritol; 1,4-butanediol; 1,6-hexanediol; 1,12-dodecandiol; and mixtures thereof.

7. The composition of claim 1 wherein the polyfunctional aliphatic or cycloaliphatic epoxy resin of the residual oligomeric product has been isolated from diglycidyl ethers of cis-, trans-1,3- and 1,4-cyclohexanedimethanols; wherein the polyfunctional aliphatic or cycloaliphatic epoxy resin of the residual oligomeric product contains less than 20% by weight of diglycidyl ethers of cis-, trans-1,3- and 1,4-cyclohexanedimethanols and comprises one or more selected from the group consisting of:

geometrical isomers of 2-propanol, 1-(oxiranylmethoxy)-3-[[3(or 4)-[(oxiranylmethoxy) methyl]cyclohexyl]methoxyl]-;

geometrical isomers of oxirane, 2-[[2-chloro-1-[[[3(or 4)-[(oxiranylmethoxy)methyl]cyclohexyl]methoxy]methyl]ethoxy]methyl]-;

geometrical isomers of oxirane, 2-[[[3(or 4)-[[2,3-bis(oxiranylmethoxy)propoxy]methyl]cyclohexyl]methoxy]methyl]-;

geometrical isomers of cyclohexanemethanol, 3(or 4)-[[2-hydroxy-3-[[3(or 4)-[(oxiranyl-methoxy)methyl]cyclohexyl]methoxy]propoxy]methyl]-;

geometrical isomers of 2-propanol, 1,3-bis[[3(or 4)-[(oxiranylmethoxy)methyl] cyclohexyl]methoxy]-; and

geometrical isomers of oxirane, 2-[[2-[[3(or 4)-[(oxiranylmethoxy)methyl]cyclohexyl]methoxy]-1-[[[3(or 4)-[(oxiranylmethoxy)methyl]cyclohexyl]methoxy]methyl]ethoxy]methyl]-.

8. The composition of claim 1 , wherein the curing material (B) comprises one or more alkyleneamine or polyalkylenepolyamine curing agents.

9. The composition of claim 1 , including (C) one or more epoxy resins other than the epoxy resin of component (A).

10. The composition of claim 9 , wherein the one or more epoxy resins, component (C), comprises one or more of aliphatic and/or cycloaliphatic epoxy resins.

11. A partially cured (B-staged) product comprising the partially cured thermosettable epoxy resin composition of claim 1 .

12. A totally cured thermoset product comprising the totally cured thermosettable epoxy resin composition of claim 1 .

13. An article made from the composition of claim 1 .

14. The article of claim 13 , wherein the article comprises a coating, a laminate, an encapsulation, a casting, a filament winding, a molding, a polymer concrete, an adhesive bond, a paint, a lacquer, a varnish, or a composite.

15. A process for preparing a thermosettable composition comprising admixing:

(A) a residual oligomeric product; wherein the residual oligomeric product comprises a polyfunctional aliphatic or cycloaliphatic epoxy resin which has been isolated from an epoxy resin product formed as a result of an epoxidation process comprising the reaction of

(i) an aliphatic or cycloaliphatic hydroxyl-containing material;

(ii) an epihalohydrin;

(iii) a basic-acting substance;

(iv) a non-Lewis acid catalyst; and

(v) optionally, one or more solvents;

(B) an epoxy curing material comprising

(i) an epoxy resin curing agent;

(ii) an epoxy resin curing catalyst; or

(iii) both (i) and (ii); and

(C) optionally, an epoxy resin compound other than the polyfunctional aliphatic or cycloaliphatic epoxy resin (A).

16. A process of curing an admixture composition comprising: preparing a thermosettable composition according to the method of claim 15 , and curing the thermosettable composition at a temperature of from about 0° C. to about 300° C.