IP Library Granted Patent US 9,745,491
Granted Patent B2
US 9,745,491 · App. 14/141,933 · Granted Aug 29, 2017

Method for producing crosslinked polymer, crosslinked polymer, and coating composition containing the same

Inventors: Yumiko Hayashi (Hirakata, JP); Sachiko Morimoto (Hirakata, JP); Manabu Yamaoka (Hirakata, JP); Naoya Yabuuchi (Hirakata, JP)
Assignee: NIPPON BEE CHEMICAL CO., LTD.
C09D133/066C08L31/00C08L31/02C08L31/06C08L33/062C08L33/064C08L33/066C08L33/14C08L2312/06
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Quick Facts
Patent No.
US 9,745,491
App. No.
14/141,933
Granted
Aug 29, 2017
Kind
B2
Abstract

The object of the present disclosure is to provide a method for producing a crosslinked polymer by radical polymerization of a monomer composition, by which method a desired crosslinked polymer can be produced in a high solid content with good productivity (also at a low production cost), and a crosslinked polymer obtained by the production method and a coating composition containing the same. A method for producing a crosslinked polymer having a weight average molecular weight of 15000 to 200000, the method comprising step [I] of obtaining a crosslinked polymer (A) by conducting polymerization of a monomer composition comprising 2 to 30% by weight of a polyfunctional methacrylate having 2 to 4 functional groups (a) and 98 to 70% by weight of one or more polymerizable monomers selected from the group consisting of monofunctional (meth)acrylates, (meth)acrylic acid, and monofunctional vinyl aromatic compounds (b) in an organic solvent in the presence of a radical polymerization initiator in a temperature region where the radical polymerization initiator comes to have a half-life of 4 to 18 minutes.

Claims (22)

1. A method for producing a crosslinked polymer in a reaction liquid without gelation, the crosslinked polymer having a weight average molecular weight of 15000 to 200000, the method comprising:

a step [I] of obtaining a crosslinked polymer (A) by conducting a polymerization of a monomer composition comprising 2 to 30% by weight of a polyfunctional methacrylate having 2 to 4 functional groups (a) and 98 to 70% by weight of one or more polymerizable monomers selected from the group consisting of monofunctional (meth)acrylates, (meth)acrylic acid, and monofunctional vinyl aromatic compounds (b) in an organic solvent, in the presence of a radical polymerization initiator, and in a temperature region where the half-life of the radical polymerization initiator is from 4 to 18 minutes;

wherein the concentration of the crosslinked polymer in the reaction liquid after completion of the step (I) is 50% or more, by weight.

2. The method for producing a crosslinked polymer according to claim 1 , wherein the one or more polymerizable monomers selected from the group consisting of monofunctional (meth)acrylates, (meth)acrylic acid, and monofunctional vinyl aromatic compounds (b) comprises a compound selected from the group consisting of (meth)acrylates having a molecular weight of less than 160, (meth)acrylic acid, and styrene in an amount of 82% by weight or more.

3. The method for producing a crosslinked polymer according to claim 1 , wherein the crosslinked polymer has one or more kinds of functional group selected from the group consisting of a hydroxy group and a carboxyl group and the content of the functional group is 10 to 160 mgKOH/g as expressed in hydroxyl value or acid value.

4. The method for producing a crosslinked polymer according to claim 1 , wherein the organic solvent is a solvent capable of dissolving the monomer composition and the crosslinked polymer.

5. The method for producing a crosslinked polymer according to claim 1 , wherein the method further comprises step [II] of obtaining an active energy ray-curable crosslinked polymer (B) by reacting a compound having a reactive functional group capable of undergoing addition reaction to the crosslinked polymer (A) and a radically polymerizable double bond (c) with the crosslinked polymer (A) after the step [I].

6. A crosslinked polymer that is a crosslinked polymer (A) obtained by the method for producing a crosslinked polymer according to claim 1 .

7. A crosslinked polymer that is a crosslinked polymer (B) obtained by the method for producing a crosslinked polymer according to claim 5 .

8. A crosslinked polymer-containing liquid comprising a crosslinked polymer (A) obtained by the method for producing a crosslinked polymer according to claim 1 .

9. A crosslinked polymer-containing liquid comprising a crosslinked polymer (B) obtained by the production method according to claim 5 .

10. A coating composition comprising a crosslinked polymer according to claim 6 .

11. A coating composition comprising a crosslinked polymer according to claim 7 .

12. The method for producing a crosslinked polymer according to claim 2 , wherein the crosslinked polymer has one or more kinds of functional group selected from the group consisting of a hydroxy group and a carboxyl group and the content of the functional group is 10 to 160 mgKOH/g as expressed in hydroxyl value or acid value.

13. The method for producing a crosslinked polymer according to claim 2 , wherein the organic solvent is a solvent capable of dissolving the monomer composition and the crosslinked polymer.

14. The method for producing a crosslinked polymer according to claim 2 , wherein the method further comprises step [II] of obtaining an active energy ray-curable crosslinked polymer (B) by reacting a compound having a reactive functional group capable of undergoing addition reaction to the crosslinked polymer (A) and a radically polymerizable double bond (c) with the crosslinked polymer (A) after the step [I].

15. A crosslinked polymer that is a crosslinked polymer (A) obtained by the method for producing a crosslinked polymer according to claim 2 .

16. A crosslinked polymer that is a crosslinked polymer (B) obtained by the method for producing a crosslinked polymer according to claim 14 .

17. A crosslinked polymer-containing liquid comprising a crosslinked polymer (A) obtained by the method for producing a crosslinked polymer according to claim 2 .

18. A crosslinked polymer-containing liquid comprising a crosslinked polymer (B) obtained by the method for producing a crosslinked polymer according to claim 14 .

19. A coating composition comprising a crosslinked polymer according to claim 15 .

20. A coating composition comprising a crosslinked polymer according to claim 16 .

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE CHANGE OF NAME DOCUMENTATION PREVIOUSLY RECORDED ON REEL 040478 FRAME 0507. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Feb 24, 2017
From: NIPPON BEE CHEMICAL CO., LTD.
To: NIPPON PAINT AUTOMOTIVE COATINGS CO., LTD
Reel/Frame 041821/0062 →
CHANGE OF NAME Recorded Oct 25, 2016
From: NIPPON BEE CHEMICAL CO., LTD.
To: NIPPON PAINT AUTOMOTIVE COATINGS CO., LTD.
Reel/Frame 040478/0507 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 27, 2013
From: HAYASHI, YUMIKO; MORIMOTO, SACHIKO; YAMAOKA, MANABU; YABUUCHI, NAOYA
To: NIPPON BEE CHEMICAL CO., LTD
Reel/Frame 031853/0895 →
Priority Claims (2)
JP 2012-285408 · Dec 27, 2012 · national
JP 2013-129945 · Jun 20, 2013 · national
Continuity (1)
Related Publication 20140187710A1 · Jul 3, 2014