(meth)acrylate functional dispersant

Patent metadata

Field	Value
Publication number	US-2023295353-A1
Application number	US-202118017103-A
Country	US
Kind code	A1
Filing date	Jul 23, 2021
Priority date	Jul 23, 2020
Publication date	Sep 21, 2023
Grant date	—

Abstract

A (meth)acrylate functional copolymer is useful as a dispersant for solid particulates in paints, inks and coatings. The copolymers have (meth)acrylate functionality positioned pendant to the polymer chain. Also positioned pendant to the polymer backbone chain are non-(meth)acrylate-functional hydrophobic and/or hydrophilic pendant groups. The copolymers are useful as dispersants in dispersions of particulate solids in organic media and aqueous media, such in paints and printing inks.

First claim

1 . A (meth)acrylate-functionalized polymer comprising at least one unit of structure [A], at least one unit of structure [B], and at least one unit of structure [C], wherein:
structure [A] is:

wherein R 1 and R 3 are the same or different and are H or alkyl, R 2 and R 4 are different and are either an organic moiety bearing at least one (meth)acrylate functional group or H; structure [B] is:

wherein R 7 and R 9 are the same or different and are H or alkyl, R 8 and R 10 are different and are independently selected from:
—(R 11 O) n R 12 , wherein R 11 is a divalent alkylene moiety, R 12 is H or a C1-C26 alkyl, and n is an integer of 1 or more;
R 19 wherein R 19 is a C2-C34 branched or straight chained alkyl;
—R 2 O—(C═O)OH wherein R 20 is a C2-C26 branched or straight chained alkylene; or
H;

and
structure [C] is:

wherein R 13 , R 14 , R 15 , and R 16 are the same or different and are independently selected from the group consisting of H and organic moieties, subject to the proviso that structure [C] is different from structure [A] and structure [B]; and
wherein one or more repeating units of structure [C] are located between at least one of i) two units of structure [A], ii) two units of structure [B], or iii) one unit of structure [A] and one unit of structure [B].

2 . The (meth)acrylate-functionalized polymer of claim 1 , wherein the (meth)acrylate-functionalized polymer is additionally comprised of repeating units of structure [D] and structure [D] is:

wherein R 17 and R 18 may be the same or different and may be selected from H or an C1 to C4 alkyl group.

3 . The (meth)acrylate-functionalized polymer of claim 1 , wherein the one or more repeating units of structure [C] are located between at least one of:
i) two units of structure [A], ii) two units of structure [B], iii) two units of structure [D], iv) one unit of structure [A] and one unit of structure [B], v) one unit of structure [A] and one unit of structure [D], or vi) one unit of structure [B] and one unit of structure [D].

4 . The (meth)acrylate-functionalized polymer of claim 1 , wherein one of R 2 or R 4 is

wherein R 5 is a divalent alkylene or an oligooxyalkylene or a poly(ester) moiety and R 6 is H or CH 3 .

5 . The (meth)acrylate-functionalized polymer of claim 4 , wherein R 5 is a poly(ester) moiety comprising caprolactone residues.

6 . The (meth)acrylate-functionalized polymer of claim 4 , wherein R 6 is H.

7 . The (meth)acrylate-functionalized polymer of claim 1 , wherein R 1 , R 3 , R 7 , and R 9 are each H.

8 . The (meth)acrylate-functionalized polymer of claim 4 , wherein R 5 is an ethylene or oligooxyethylene.

9 . The (meth)acrylate-functionalized polymer of claim 1 , wherein R 13 is phenyl, alpha methyl phenyl, methyl, methoxy, ethoxy, or C2-C20 alkyl and R 14 , R 15 and R 16 are each H.

10 . The (meth)acrylate-functionalized polymer of claim 1 , wherein R 11 is a divalent ethylene or propylene moiety.

11 . The (meth)acrylate-functionalized polymer of claim 1 , wherein R 12 is a C8-C26 straight chain saturated alkyl.

12 . The (meth)acrylate-functionalized polymer of claim 1 , wherein n is an integer of 3 to 30.

13 . The (meth)acrylate-functionalized polymer of claim 1 , wherein R 19 is a branched saturated alkyl.

14 . The (meth)acrylate-functionalized polymer of claim 1 , having a number average molecular weight of from 1000 to 50,000 Daltons.

15 . A curable composition, wherein the curable composition is comprised of a (meth)acrylate-functionalized polymer in accordance with claim 1 and an ethylenically unsaturated curable species other than the (meth)acrylate-functionalized polymer in accordance with claim 1 .

16 . The curable composition of claim 15 , wherein the curable composition is comprised of a matrix which is liquid at 25° C. in which solid particles of a substance are dispersed.

17 . The curable composition of claim 16 , wherein the substance is selected from the group consisting of fillers, pigments, and inorganic pigments.

18 . A method of dispersing solid particles of a substance in a liquid matrix comprised of one or more ethylenically unsaturated curable species, wherein the method comprises incorporating an effective amount of at least one (meth)acrylate-functionalized polymer in accordance with claim 1 in the liquid matrix.

19 . A (meth)acrylate-functionalized polymer, wherein the (meth)acrylate-functionalized polymer is a reaction product of at least i) an anhydride-functionalized base (meth)acrylate-functionalized polymer, ii) a hydroxyl-functionalized (meth)acrylate, and iii) an alkoxylated long chain aliphatic alcohol.

20 . The (meth)acrylate-functionalized polymer of claim 19 , wherein the anhydride-functionalized base (meth)acrylate-functionalized polymer is a co(meth)acrylate-functionalized polymer of maleic anhydride and at least one co-monomer.

21 . The (meth)acrylate-functionalized polymer of claim 19 , wherein the hydroxyl-functionalized (meth)acrylate is selected from the group consisting of hydroxyalkyl (meth)acrylates and alkoxylated hydroxyalkyl (meth)acrylates.

22 . The (meth)acrylate-functionalized polymer of claim 19 , wherein the alkoxylated long chain aliphatic alcohol is an ethoxylate of a C8-C26 aliphatic alcohol.

Assignees

• Arkema France

Inventors

• Li Ling
• Hazell Thomas W
• Shurdha Endrit

Classifications

• C08F222/08 Primary

  with vinyl aromatic monomers · CPC title

• C08F20/20 Primary

  of polyhydric alcohols or {polyhydric} phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F8/14

  Esterification · CPC title

• C08F2810/20

  leading to a crosslinking, either explicitly or inherently · CPC title

• C08F2810/30

  leading to the formation or introduction of aliphatic or alicyclic unsaturated groups · CPC title