Epoxy composition

Patent metadata

Field	Value
Publication number	US-10144843-B2
Application number	US-201415514768-A
Country	US
Kind code	B2
Filing date	Sep 30, 2014
Priority date	Sep 30, 2014
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

A modified epoxy novolac resin composition including a reaction product of: (a) a novolac epoxy resin compound, (b) a cardanol compound, and (c) a catalyst compound; and a process for preparing the above modified epoxy novolac resin composition such that the composition contains cardanol moieties in a concentration of at least 15 weight percent of the composition.

First claim

The invention claimed is:

1. A modified epoxy novolac resin composition comprising a compound having the following structure:

wherein X is

wherein the X moieties represented by Structure (III) are present in the composition at a concentration of about 15 weight percent to about 40 weight percent; and wherein: R 1 is hydrogen or alkyl group of from 1-12 carbon atoms, R 2 is a straight-chain with 15 carbons containing 0 to 3 C═C bond(s) selected from —C 15 H 31 , —C 15 H 29 , —C 15 H 27 , and —C 15 H 25 , and n is a numeral from 1 to 10.

2. The modified epoxy novolac resin composition of claim 1 , having a viscosity of less than about 4,000 mPa·s at 70° C.

3. A curable epoxy novolac resin composition comprising:
(i) the modified epoxy novolac resin composition of claim 1 ; and
(ii) at least one hardener compound.

4. The curable resin composition of claim 3 , further comprising an epoxy compound different from the modified epoxy novolac resin composition (i).

5. The curable resin composition of claim 3 , wherein the at least one hardener compound comprises an amine hardener, and the curable resin composition features an epoxide to amine hydrogen equivalent ratio of from about 0.3:1 to about 1.3:1.

6. The curable resin composition of claim 3 , wherein the at least one hardener compound comprises an amine hardener, and the curable resin composition features an epoxide to amine hydrogen equivalent ratio of from about 0.6:1 to about 1.2:1.

7. The curable resin composition of claim 3 , wherein the at least one hardener compound comprises an amine hardener, and the curable resin composition features an epoxide to amine hydrogen equivalent ratio of from about 0.7:1 to about 1.0:1.

8. The curable resin composition of claim 3 , wherein the at least one hardener compound comprises an amine hardener.

9. The curable resin composition of claim 3 , wherein the modified epoxy novolac resin composition (i) and the at least one hardener compound (ii) exhibit a compatibility sufficient to provide the curable resin composition with an induction time of from about 30 minutes to about 60 minutes.

10. The curable resin composition of claim 3 , having a pot-life of greater than or equal to 60 minutes.

11. The curable resin composition of claim 3 , having a solids content of from about 50 weight percent to about 80 weight percent.

12. A process for preparing a curable epoxy novolac resin composition comprising admixing: (i) the modified epoxy novolac resin composition of claim 1 , and (ii) at least one hardener compound.

13. A coating comprising a reaction product of:
(I) the modified epoxy novolac resin composition of claim 1 ;
(II) at least one hardener compound; and
(III) optionally, a pigment.

14. The coating of claim 13 , wherein the coating exhibits a chemical resistance property when the coating is subject to a chemical substance selected from the group consisting of formic acid, acetic acid, nitric acid, sulfuric acid, and methanol.

15. The coating of claim 14 , wherein the coating exhibits an observable increase in chemical resistance compared to a coating made from a conventional epoxy novolac resin compound; wherein the chemical resistance is from 0 to about 3 as measured by a numerical rating scale of 0 to 5 wherein “0” means no blistering is observed and “5” means blistering is observed.

16. A process for preparing a thermoset comprising:
(i) providing an admixture of: (I) the modified epoxy novolac resin composition of claim 1 and (II) at least one hardener compound, to form a curable composition; and
(ii) curing the curable composition of step (i).

17. A cured thermoset article prepared by the process of claim 16 .

18. A modified epoxy novolac resin composition comprising a reaction product of a reaction mixture comprising: (a) a novolac epoxy resin compound, (b) a cardanol compound, and (c) a catalyst compound; wherein the reaction product features both reacted and unreacted epoxy groups of (a), said reacted epoxy groups are a ring opening reaction product of an epoxy group of (a) and the hydroxyl group of (b); and wherein the reacted epoxy groups are present in the composition at a concentration of about 15 weight percent to about 40 weight percent.

19. The modified epoxy novolac resin composition of claim 18 , wherein the cardanol compound, component (b), has a purity of at least 80 percent.

20. The modified epoxy novolac resin composition of claim 18 , wherein the cardanol compound, component (b), has a purity of from at least 80 percent to about 100 percent.

21. The modified epoxy novolac resin composition of claim 18 , wherein the novolac epoxy resin compound, component (a), is derived from phenol.

22. The modified epoxy novolac resin composition of claim 18 , wherein the novolac epoxy resin compound, component (a), is represented by the following structure:

wherein n is a numeral from 1 to 10.

23. The modified epoxy novolac resin composition of claim 18 , wherein the catalyst compound, component (c), is a phosphonium salt.

24. The modified epoxy novolac resin composition of claim 18 , wherein the catalyst compound, component (c), is ethyl triphenyl phosphonium acetate.

25. The modified epoxy novolac resin composition of claim 18 , wherein component (a) is present in the reaction mixture at a concentration of from about 40 weight percent to about 85 weight percent; wherein component (b) is present in the reaction mixture at a concentration of from about 15 weight percent to about 60 weight percent; and wherein component (c) is present in the reaction mixture at a concentration of from about 50 parts per million to about 1,000 parts per million.

26. A process for preparing a modified epoxy novolac resin composition comprising forming a reaction product of a reaction mixture comprising: (a) a novolac epoxy resin compound, (b) a cardanol compound, and (c) a catalyst compound; wherein the reaction product features both reacted and unreacted epoxy groups of (a), said reacted epoxy groups are a ring opening reaction product of an epoxy group of (a) and the hydroxyl group of (b); and wherein the reacted epoxy groups are present in the composition at a concentration of about 15 weight percent to about 40 weight percent.

Assignees

• Blue Cube Ip Llc

Inventors

• Shen Yue
• Zhan fu
• Drumright Ray E
• Wu Yan

Classifications

• C08G59/5033

  aromatic · CPC title

• C08G59/3218

  Carbocyclic compounds · CPC title

• C08G59/688

  containing phosphorus · CPC title

• C09D163/04 Primary

  Epoxynovolacs · CPC title

• C08L63/10

  Epoxy resins modified by unsaturated compounds · CPC title