Hydroxyl group-containing (meth)acrylate oligomer, prepolymer therefrom, and method for use thereof

• US 4,691,045 A
• Filed: 12/05/1985
• Issued: 09/01/1987
• Est. Priority Date: 12/06/1984
• Status: Expired due to Fees

• Current Assignee: Nippon Shokubai Kagaku Kogyo Company Limited 5-1 Koraibashi Higashi-Ku Osaka Japan
• Original Assignee: Nippon Shokubai Company Limited
• Inventors: Fukuchi, Shuzo, Yamaguchi, Shigeru
• Primary Examiner(s): Michl, Paul R.
• Application Number:
  US06/805,342
• Time in Patent Office: 635 Days
• Field of Search: 522/95, 522/96, 522/154, 526/320, 560/185
• US Class Current: 560/185
• CPC Class Codes: C08F 20/28 containing no aromatic rings in the alcohol moiety
• CPC Class Codes: C08F 290/062 Polyethers

Abstract

A hydroxyl group-containing (meth)acrylate oligomer represented by the general formula I: ##STR1## wherein two R¹ '"'"'s independently stand for hydrogen atom or methyl group, two Z'"'"'s independently stand for a divalent organic group of 2 to 20 carbon atoms, and p stands for an integer of the value of 1 to 100, and urethane, carboxyl and hydroxyl modified prepolymer thereof.

Claims

1. A hydroxyl group-containing (meth)acrylate oligomer represented by the general formula I:

##STR30## wherein two R¹ '"'"'s independently stand for hydrogen atom or methyl group, two Z'"'"'s independently stand for a divalent hydrocarbon group of 2 to 20 carbon atoms, and p stands for an integer of the value of 1 to 100.

2. A hydroxyl group-containing (meth)acrylate oligomer according to claim 1, wherein the symbol Z in the general formula stands for a divalent hydrocarbon group of 2 to 6 carbon atoms.

3. A hydroxyl group-containing (meth)acrylate oligomer according to claim 1, wherein the symbol p in the general formula stands for an integer of the value of 1 to 20.

13. A curable composition containing as an essintial component thereof a hydroxyl group-containing (meth)acrylate oligomer according to claim 1.

14. A composition according to claim 13, which further contains an ethylenically unsaturated compound.

17. A curable composition, comprising at least one of the curable compositions according to claim 13 and a photo initiator.

18. A curable composition, comprising at least one of the curable compositions according to claim 13 and a radical polymerization initiator.

19. A coating composition preponderantly comprising a curable composition according to claim 17.

20. A coating composition preponderantly comprising a curable composition according to claim 18.

21. An adhesive composition preponderantly comprising a curable composition according to claim 17.

22. An adhesive composition preponderantly comprising a curable composition according to claim 18.

4. A method for the production of a hydroxyl group-containing (meth)acrylate oligomer represented by the general formula I:

##STR31## wherein two R¹ '"'"'s independently stand for hydrogen atom or methyl group two Z'"'"'s independently stand for a divalent hydrocarbon group of 2 to 20 carbon atoms, and p stands for an integer of the value of 1 to 100, which method comprises addition polymerizing a hydroxyl group-containing (meth)acrylate represented by the general formula IV;

##STR32## wherein R¹ stands for hydrogen atom or methyl group and Z stands for a divalent hydrocarbon group of 2 to 20 carbon atoms, in the presence of a catalyst thereby converting said hydroxyl group-containing (meth)acrylate into an oligomer.

5. A method according to claim 4, wherein said catalyst is at least one member selected from the group consisting of protonic acid, Lewis acids, oxy sulfates, heteropoly acids and salts thereof, and isopoly acids.

6. A method according to claim 5, wherein said catalyst is a heteropoly acid.

7. A method according to claim 4, wherein said reaction is carried out at a temperature in the range of 10°

to 150°

C.

8. A method according to claim 4, wherein the symbol Z in the general formula stands for a divalent organic group of 2 to 6 carbon atoms.

9. A method according to claim 4, wherein the symbol p in the general formula stands for an integer of the value of 1 to 20.

10. A method according to claim 4, wherein said hydroxyl group-containing (meth)acrylate represented by the general formula IV is a hydroxyalkyl (meth)acrylate.

11. A hydroxyl group-containing (meth)acrylate prepolymer, comprising the reaction product of a hydroxyl group-containing compound (E) containing as an essential component thereof a hydroxyl group-containing (meth)acrylate oligomer (A) represented by the general formula I:

##STR33## wherein two R¹ '"'"'s independently stand for hydrogen atom or methyl group, two Z'"'"'s independently stand for a divalent organic group of 2 to 20 carbon atoms, and p stands for an integer of the value of 1 to 100, with an oxygen-containing cyclic compound (F) and optionally further with a carboxylic group containing compound (G).

12. A hydroxyl group-containing (meth)acrylate prepolymer according to claim 11, wherein said oxygen-containing cyclic compound is a lactone.

15. A curable composition containing as an essential component thereof a hydroxyl group-containing (meth)acrylate prepolymer according to claim 11.

16. A composition according to claim 15, which further contains an ethylenically unsaturated compound.