Preparation and use of branched polymers containing hydroxyl and acrylate groups

• US 9,267,053 B2
• Filed: 05/06/2011
• Issued: 02/23/2016
• Est. Priority Date: 05/10/2010
• Status: Active Grant

• Current Assignee: Construction Research & Technology GmbH (BASF SE)
• Original Assignee: BASF SE
• Inventors: Klok, Harm-Anton, Ji, Sanhao, Bruchmann, Bernd
• Primary Examiner(s): Wu, David W
• Assistant Examiner(s): REDDICK, MARIE L
• Application Number:
  US13/102,379
• Publication Number:
  US 20110275759A1
• Time in Patent Office: 1,754 Days
• Field of Search: 524/592, 524/593, 524/597, 528/230, 528/245
• US Class Current: 1/1
• CPC Class Codes: C08G 16/02 of aldehydes
• CPC Class Codes: C09D 133/04 Homopolymers or copolymers of esters C09D143/04 takes precedence
• CPC Class Codes: C09D 161/00 Coating compositions based on condensation polymers of aldehydes or ketones with polyalcohols C09D159/00; with polynitriles C09D177/00; Coating compositions based on derivatives of such polymers

Abstract

The present invention relates to branched polymers which contain hydroxyl groups and acrylate groups, to processes for preparing them, and to their use.

Claims

1. A branched polymer (S),

obtained by a process comprising reacting a carbonyl compound (A) and an acrylate compound (B),

wherein said branched polymer (S) comprises a hydroxyl group and an acrylate group, and

wherein the carbonyl compound (A) is at least one carbonyl compound selected from the group consisting of a carbonyl compound (Ax) having more than two carbonyl groups and a dicarbonyl compound (A2) having just two carbonyl groups, the more than two carbonyl groups of the carbonyl compound (Ax) and the just two carbonyl groups of the dicarbonyl compound (A2) are selected independently from the group consisting of an aldehyde group and a keto group, and

wherein the acrylate compound (B) is at least one acrylate compound selected from the group consisting of an acrylate compound (By) having more than two acrylate groups and a diacrylate compound (B2), in which an average functionality of the carbonyl compound (A), the acrylate compound (B), or a combination thereof, is more than 2.

2. The polymer according to claim 1, wherein said acrylate compound (By) is present and is reacted in the presence of the dicarbonyl compound (A2).

3. The polymer according to claim 1, wherein said acrylate compound (By) and said diacrylate compound (B2) are present and are reacted in the presence of the dicarbonyl compound (A2).

4. The polymer according to claim 1, wherein the carbonyl compound (Ax) and the dicarbonyl compound (A2) are present and each comprise exclusively aldehyde groups.

5. The polymer according to claim 1, wherein said carbonyl compound (Ax) is present and which is at least one carbonyl compound selected from the group consisting of 1,2,3-benzenetrialdehyde, 1,2,4-benzenetrialdehyde, 1,3,5-benzenetrialdehyde and 2,4,6-pyridinetrialdehyde.

6. The polymer according to claim 1, wherein said dicarbonyl compound (A2) is present and is at least one carbonyl compound selected from the group consisting of glyoxal, succinaldehyde, glutaraldehyde, caproaldehyde, furan-2,5-dialdehyde, pyrrole-2,5-dialdehyde, pyridin-2,6-dialdehyde, phthalaldehyde, isophthalaldehyde and terephthalaldehyde.

7. The polymer according to claim 1, wherein said to acrylate compound (By) is present and which is at least one acrylate compound selected from the group consisting of a polyether acrylate, a polyester acrylate, an acrylated polyacrylateol, a urethane acrylate and an acrylic ester of an optionally alkoxylated polyol.

8. The polymer according to claim 1, wherein said acrylate compound (By) is present and which is an acrylic ester of an optionally alkoxylated polyol of formulae (IIa) to (IIc):

9. The polymer according to claim 1, wherein said acrylate compound (By) is present and is at least one acrylate compound selected from the group consisting of trimethylolpropane triacrylate, pentaerythritol tetraacrylate, glyceryl triacrylate, a triacrylate of singly to vigintuply ethoxylated trimethylolpropane and a triacrylate of singly to vigintuply ethoxylated glycerol.

10. A process for producing a polymer according to claim 1, the process comprising:

reacting the carbonyl compound (A)

and the acrylate compound (B) at a temperature between 0°

C. and 100°

C., in the presence of a tertiary amine or phosphine, in a stoichiometry between the acrylate compound and the carbonyl compound of from 1;

0.05 to 1;

1.5, optionally in the presence of a solvent.

11. A coating material for a multi-cure application, the coating material comprising:

the polymer according to claim 1.

12. The polymer according to claim 1, wherein said process comprises reacting said carbonyl compound (A) and said acrylate compound (B) in the presence of a Baylis-Hillman reaction catalyst.

13. The polymer according to claim 12, wherein said Baylis-Hillman reaction catalyst is at least one catalyst selected from the group consisting of a tertiary amine and a phosphine.

14. The polymer according to claim 1, wherein said process comprising reacting a carbonyl compound (A) and an acrylate compound (B) is a Baylis-Hillman reaction.