Epoxy resin compositions

Patent metadata

Field	Value
Publication number	US-10414854-B2
Application number	US-201515126718-A
Country	US
Kind code	B2
Filing date	Feb 26, 2015
Priority date	Mar 24, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

A process for preparing an aliphatic or cycloaliphatic epoxy resin composition including the steps of: (I) reacting a mixture of the following components: (a) an aliphatic or cycloaliphatic hydroxyl-containing material, (b) an epihalohydrin, (c) a stoichiometric excess of a base compound or basic acting substance, (d) a catalyst, and (e) optionally, a solvent; wherein the reacting step (I) is carried out under reaction conditions sufficient to form a crude aliphatic or cycloaliphatic epoxy resin composition product in the resultant reaction mixture; (II) neutralizing the resultant reaction mixture of step (I) containing the crude aliphatic or cycloaliphatic epoxy resin composition product with a phosphate neutralizing agent sufficient to partially neutralize the base or basic acting substance and to form a neutralized fluid medium containing aliphatic or cycloaliphatic epoxy resin composition product; (III) removing at least a portion of unreacted epihalohydrin from the reaction mixture of step (II); and (IV) subjecting the reaction mixture of step (III) above to a separation process to recover the aliphatic or cycloaliphatic epoxy resin composition product from the neutralized fluid medium; wherein the aliphatic or cycloaliphatic epoxy resin composition product yield is greater than about 70 percent.

First claim

The invention claimed is:

1. A process for preparing an aliphatic or cycloaliphatic epoxy resin composition comprising the steps of:
(I) reacting a mixture of the following components:
(a) an aliphatic or cycloaliphatic hydroxyl-containing material,
(b) an epihalohydrin,
(c) a stoichiometric excess of a base compound or basic acting substance,
(d) a catalyst, and
(e) optionally, a solvent; wherein the reacting step (I) is carried out under reaction conditions sufficient to form a crude aliphatic or cycloaliphatic epoxy resin composition product in the resultant reaction mixture;

(II) neutralizing the resultant reaction mixture of step (I) containing the crude aliphatic or cycloaliphatic epoxy resin composition product with a phosphate neutralizing agent sufficient to partially neutralize the base or basic acting substance and to form a neutralized fluid medium containing aliphatic or cycloaliphatic epoxy resin composition product;
(III) removing at least a portion of unreacted epihalohydrin from the reaction mixture of step (II); and
(IV) subjecting the reaction mixture of step (III) above to a separation process to recover the aliphatic or cycloaliphatic epoxy resin composition product from the neutralized fluid medium; wherein the aliphatic or cycloaliphatic epoxy resin composition product yield is greater than about 70 percent;
and wherein the amount of neutralizing agent used in the present process is from about 5 weight percent to about 80 weight percent of the stoichiometric excess of the base utilized during the reaction step (I).

2. The process of claim 1 , wherein the aliphatic or cycloaliphatic hydroxyl containing material is cis- and trans-1,3- and 1,4-cyclohexanedimethanol; or cis and trans-1,4-cyclohexanedimethanol; and wherein the product produced is cyclohexanedimethanol epoxy resin.

3. The process of claim 1 , wherein the epihalohydrin is epichlorohydrin.

4. The process of claim 1 , wherein the base compound is sodium hydroxide.

5. The process of claim 1 , wherein the catalyst is a non-Lewis acid catalyst.

6. The process of claim 5 , wherein the non-Lewis acid catalyst is benzyltriethylammonium chloride.

7. The process of claim 1 , wherein the fluid medium of the neutralizing step is water.

8. The process of claim 1 , wherein the neutralizing agent is an aqueous solution of monosodium phosphate, potassium dihydrogen phosphate, phosphoric acid, and mixtures thereof.

9. The process of claim 1 , wherein the neutralizing agent is an aqueous solution of sodium dihydrogen phosphate.

10. The process of claim 1 , wherein the neutralizing agent is used in an amount sufficient to achieve a pH of from about 7 to about 13.

11. The process of claim 1 , wherein the neutralizing agent is an aqueous solution of sodium dihydrogen phosphate; and wherein the aqueous solution contains from about 5 weight percent neutralizing agent to about 13 weight percent neutralizing agent.

12. The process of claim 1 , wherein the amount of base, component (c) in step (I), is from about 1 molar equivalent to about 2 molar equivalents of base to the hydroxyl groups in the aliphatic or cycloaliphatic hydroxyl-containing material, component (a).

13. The process of claim 1 , wherein the resultant reaction mixture in step (I) is neutralized sufficient to provide an amount of insoluble polymeric material in the product of less than about 10 weight percent.

14. The process of claim 1 , wherein at least a portion of the unreacted epihalohydrin isolated in step (III) is recycled to step (I).

Assignees

• Blue Cube Ip Llc

Inventors

• Hefner Jr Robert E
• Beigzadeh Daryoosh
• Couling David J
• Coyle Robert W
• Carr David A

Classifications

• C07D301/28

  by reaction with hydroxyl radicals · CPC title

• C08G59/04 Primary

  of polyhydroxy compounds with epihalohydrins or precursors thereof · CPC title

• C08K5/56

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title

• C08G59/686

  containing nitrogen · CPC title