Curable lactone derived resins

• US 4,188,472 A
• Filed: 10/06/1978
• Issued: 02/12/1980
• Est. Priority Date: 10/06/1978
• Status: Expired due to Term

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Chang, Wen-Hsuan
• Primary Examiner(s): Welsh, Maurice J.
• Application Number:
  US05/949,181
• Time in Patent Office: 494 Days
• Field of Search: 528/75
• US Class Current: 528/75
• CPC Class Codes: C08G 18/4269 Lactones
• CPC Class Codes: C08G 18/6725 containing ester groups other than acrylate or alkylacrylate ester groups
• CPC Class Codes: Y10S 525/92 Polyurethane having terminal ethylenic unsaturation

Abstract

Curable lactone derived resins are the reaction product of (a) a lactone modified resin of the formula ##STR1## wherein X is the organic radical formed by removing at least one hydroxyl hydrogen atom from an ester containing from 1 to 3 acrylyl or alpha-substituted acrylyl groups and one or two hydroxyl groups, R is hydrogen or an alkyl group having from 1 to 12 carbon atoms, x is from 4 to 7 wherein at least (x+ 2) R'"'"'s are hydrogen, n has an average value of from about 0.2 to about 5 and a is 1 or 2; and (b) an isocyanate.

The lactone derived resins are especially useful for floor tile coatings which are UV curable. The coatings are abrasion resistant, yet are flexible.

Claims

1. A curable lactone derived resin which is the reaction product of:

(a) from about 30 percent to about 95 percent by weight of a lactone modified resin of formula ##STR6## wherein X is the organic radical formed by removing at least one hydroxyl hydrogen atom from an ester containing from 1 to 3 acrylyl or alpha-substituted acrylyl groups and one or two hydroxyl groups, R is hydrogen or an alkyl group having from 1 to 12 carbon atoms, x is from 4 to 7 and at least (x+2) R'"'"'s are hydrogen, n has an average value of from about 0.2 to about 5, and a is 1 or 2; and

(b) from about 5 percent to about 70 percent by weight of an isocyanate.

2. The lactone derived resin of claim 1, wherein the isocyanate is derived from a monoisocyanate, diisocyanate, triisocyanate or mixtures thereof.

3. The lactone derived resin of claim 2, wherein x is 4 and at least six of the R'"'"'s are hydrogen.

4. The lactone derived resin of claim 3, wherein a is 1.

5. The lactone derived resin of claim 3, wherein a is 2.

6. The lactone derived resin of claim 3, wherein the lactone modified resin is derived from epsilon-caprolactone.

7. The lactone derived resin of claim 2, wherein X is derived from a hydroxyalkyl acrylate or methacrylate.

8. The lactone derived resin of claim 7, wherein the hydroxyalkyl acryklate or methacrylate is hydroxyethyl acrylate.

9. The lactone derived resin of claim 2, wherein X is derived from the reaction product of an acrylic or methacrylic acid and an epoxy compound.

10. The lactone derived resin of claim 2 wherein X is derived from the reaction product of an acrylic or methacrylic acid and a polyol.

11. The lactone derived resin of claims 1 or 2 being the reaction product of from about 50 percent to about 80 percent by weight of the lactone modified resin and from about 20 percent to about 50 percent by weight of the isocyanate.

12. The lactone derived resin of claims 7, 9 or 10 being the reaction product of the lactone modified resin, the isocyanate and up to about 20 percent by weight of a polyol.

13. A process of making a UV curable lactone derived resin, comprising the steps of:

(a) reacting a (1) lactone of formula ##STR7## wherein R is hydrogen or an alkyl group having from 1 to 12 carbon atoms, x is from 4 to 7, and at least (x+2) R'"'"'s are hydrogen with (2) an ester containing from 1 to 3 acrylyl or alpha-substituted acrylyl groups and one or more hydroxyl groups; and

(b) reacting from about 30 percent to about 95 percent by weight of the product of step (a) with from about 5 percent to about 70 percent by weight of an isocyanate to form the lactone derived resin.

14. The process of claim 13, wherein the isocyanate is a monisocyanate, diisocyanate, triisocyanate or mixture thereof.

15. The process of claims 13 or 14, wherein x is 4 and at least six of the R'"'"'s are hydrogen.

16. The process of claim 14, wherein the ester is a hydroxyalkyl acrylate and methacrylate having from 2 to 10 carbon atoms in the alkyl group.

17. The process of claim 16, wherein the hydroxyalkyl acrylate or methacrylate is hydroxyalkyl acrylate.

18. The process of claim 17, wherein an epsilon-caprolactone is reacted with hydroxyethyl acrylate.

19. The process of claim 14, wherein the ester is derived from the reaction of an acrylic or methacrylic acid with an epoxy component.

20. The process of claim 14 wherein the ester is derived from the reaction of an acrylic or methacrylic acid with a polyol.

21. The process of claims 16, 19, or 20 wherein up to about 20 percent by weight of a polyol is reacted with the product of step (a) and the isocyanate.

22. The process of claim 13 wherein the molar ratio of the lactone to the hydroxyl groups in the ester is from about 1:

0.1 to about 1;

5.

23. The process of claim 22 wherein from about 50 percent to about 80 percent by weight of the product of step (a) is reacted with from about 20 percent to about 50 percent by weight of the isocyanate.