Epoxide derivatives of ester diol alkoxylates and compositions thereof

• US 4,195,160 A
• Filed: 01/04/1979
• Issued: 03/25/1980
• Est. Priority Date: 09/29/1977
• Status: Expired due to Term

• Current Assignee: Union Carbide Corporation (Dow, Inc.)
• Original Assignee: Union Carbide Corporation (Dow, Inc.)
• Inventors: Smith, Oliver W., Koleske, Joseph V., Knopf, Robert J.
• Primary Examiner(s): Phynes, Lucille M.
• Application Number:
  US06/000,883
• Time in Patent Office: 446 Days
• Field of Search: 528/273, 528/297, 260/835
• US Class Current: 528/297
• CPC Class Codes: C08G 18/3221 hydroxylated esters of carboxylic acids other than higher fatty acids
• CPC Class Codes: C08G 18/4887 containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
• CPC Class Codes: C08G 65/2615 the other compounds containing carboxylic acid, ester or anhydride groups
• CPC Class Codes: C08G 65/329 with organic compounds
• CPC Class Codes: C08G 65/3324 cyclic
• CPC Class Codes: C08G 65/33348 containing isocyanate group
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 2666/16 Addition or condensation polymers of aldehydes or ketones according to C08L59/00 - C08L61/00; Derivatives thereof
• CPC Class Codes: C08L 61/00 Compositions of condensation polymers of aldehydes or ketones with polyalcohols C08L59/00; with polynitriles C08L77/00; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 67/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C08L67/06 takes precedence
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: C09D 167/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds C09D167/06 takes precedence

Abstract

Derivatives of esterdiol alkoxylates obtained by reaction thereof with an epoxide, as well as the anhydride capped products thereof. Formulations containing the above are also claimed.

Claims

1. An epoxide modified ester diol alkoxylate comprising the reaction product of (A) an ester diol alkoxylate of the general formula:

##STR16## wherein m is an integer having a value of from 2 to 4, n is an integer having a value of from 1 to 5, x and y are integers each having a value of from 1 to 20 and R is an alkyl group having from 1 to 8 carbon atoms; and

(B) from 0.2 to 1 mole of a diepoxide per mole of (A).

2. An epoxide modified ester diol alkoxylate as claimed in claim 1, wherein Component (B) is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

3. An epoxide modified ester diol alkoxylate as claimed in claim 1, wherein m has a value of 2 to 3, n has a value of 1 to 3, x and y each have values of from 1 to 10 and R is an alkyl group having from 1 to 3 carbon atoms.

4. An epoxide modified ester diol alkoxylate as claimed in claim 1, wherein m has a value of 2, n has a value of 1 and R is a methyl group.

5. An epoxide modified ester diol alkoxylate as claimed in claim 1, wherein m has a value of 3, n has a value of 1 and R is a methyl group.

6. An epoxide modified ester diol alkoxylate as claimed in claim 1, wherein from 0.3 to 0.6 mole of diepoxide per mole of Component (A) is initially charged and reacted.

7. An epoxide modified ester diol alkoxylate as claimed in claim 1, wherein in said Component (A) m has a value of 2, n has a value of 1, x plus y have an average value of 4 and R is hydrogen, and said Component (B) is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

8. An epoxide modified ester diol alkoxylate as claimed in claim 7, wherein the average value of x plus y is 2.

9. An epoxide modified ester diol alkoxylate as claimed in claim 7, wherein the average value of x plus y is 6.

10. An epoxide modified ester diol alkoxylate as claimed in claim 7, wherein the average value of x plus y is 10.

11. A high solids composition comprising an epoxide modified ester diol alkoxylate as claimed in claim 1 and additionally containing from 25 to 200 weight percent thereof of a crosslinking agent.

12. A high solids composition as claimed in claim 11, wherein said crosslinking agent is hexamethoxymethylmelamine.

13. A high solids composition as claimed in claim 11, wherein Component (B) is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

14. A high solids composition as claimed in claim 11, wherein a low molecular weight polyol having from 2 to 6 hydroxyl groups and a molecular weight of from 62 to 1,000 is additionally present.

15. A high solids composition as claimed in claim 11, wherein a polycaprolactone polyol is additionally present.

16. An epoxide modified ester diol alkoxylate as claimed in claim 1, said alkoxylate capped with from 0.1 to 1 anhydride equivalent per hydroxyl equivalent initially charged with an intramolecular anhydride of a polycarboxylic acid.

17. A high solids composition comprising an anhydride capped epoxide modified ester diol alkoxylate as claimed in claim 16 and from 25 to 200 weight percent thereof of a crosslinking agent.

18. A high solids composition as claimed in claim 17, wherein said crosslinking agent is hexamethoxymethylmelamine.

19. A high solids composition as claimed in claim 17, wherein a low molecular weight polyol having from 2 to 6 hydroxyl groups and a molecular weight of from 62 to 1,000 is additionally present.

20. A high solids composition as claimed in claim 17, wherein a polycaprolactone polyol is additionally present.