Acrylic dispersants with fused aromatic imide anchor groups

Patent metadata

Field	Value
Publication number	US-11649309-B2
Application number	US-202016912820-A
Country	US
Kind code	B2
Filing date	Jun 26, 2020
Priority date	Nov 4, 2013
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

Polymeric dispersants are disclosed that include an acrylic backbone at least one pendantly attached imide group, wherein the carbonyl of the imide are chemically bonded to a fused aromatic ring. The aromatic ring can be substituted with various electron withdrawing or releasing groups. Desirably dispersant also includes solvent-solubilising chains of polyether, polyester, polyacrylate, and or polyolefin.

First claim

What is claimed is:

1. A polymeric dispersant comprising an olefinic backbone derived from polymerizing alpha-beta unsaturated olefinic monomers, wherein (i) at least 80 wt. % of the backbone repeat units are derived from polymerizing monomers which have the alpha-beta-olefin portion represented by (meth)acrylic acid, CH═C(G)-C(═O)—Z—, CH═C(G)

wherein G is selected from the group consisting of H and CH 3 ; and Z is a nitrogen or oxygen linking atom; ii) at least one of the monomers used to form the backbone is functionalized prior to or subsequent to polymerization with at least one imide group wherein the carbonyl groups of the imide are chemically bonded directly to carbon atoms of a fused aromatic ring; iii) wherein said dispersant has a number average molecular weight from about 1000 to about 100,000 g/mole; and iv) wherein said dispersant has at least one polymeric backbone block characterized as being an anchoring block that has chemically attached thereto said imide group and said polymeric backbone has also attached thereto at least one polymeric segment of 300 to 5000 g/mole molecular weight characterized as a solvent solubilizing polymeric segment;
wherein the dispersant has a structure according to formula 1 below

wherein each G independently is a CH 3 or H group or mixtures thereof
A is a moiety comprising a fused aromatic imide group,
B is a pendant moiety off a —CH 2 —C(G)- derived from polymerizing ethylenically unsaturated monomers of which at least 80 mole percent are selected from the group consisting of (meth)acrylic acid, CH═C(G)-C(═O)—Z—,

wherein G is selected from the group consisting of H and CH 3 ; and Z is a nitrogen or oxygen linking atom;
C is a pendant moiety off a —CH 2 —C(G)- derived from polymerizing ethylenically unsaturated monomers of which at least 80 mole percent are selected from the group consisting of (meth)acrylic acid, CH═C(G)-C(═O)—Z—,

wherein G is selected from the group consisting of H and CH 3 ; and Z is a nitrogen or oxygen linking atom;
(meth)acrylic acid and CH═C(G)-C(═O)—Z—, are defined to be (meth)acrylic acids and esters of acrylic acid where the ester has an alkoxy group that has from 1 to 25 carbon atoms and optionally includes an epoxide group or hydroxyl group,
D is a moiety comprising polyether, polyester, polyacrylate, polyurethane, polyolefin and mixtures thereof having a number average molecular weight from about 300 to about 5000 g/mole and attached via a linking group to the polymer backbone or is derived from polymerizing a macromonomer comprising an ethylenically unsaturated group and a pendant polyether, polyester, polyacrylate, polyurethane, polyolefin and mixtures thereof having said 300 to 5000 g/mole molecular weight, K is from 1 to 50, L and J are each from about 0 to 499, and N is from 1 to 50, E is 1 or 2 and is the number of anchoring blocks, and F is 1 or 2 and is the number of solvent-solubilizing polymeric segments, with the proviso that if E is 1, F is 2 and if F is 1, E is 2.

2. The polymeric dispersant according to claim 1 , wherein said dispersant has said at least one anchoring backbone portion and chemically bonded to backbone portion is said at least one polymeric segment characterized as a solvent solubilizing polymeric segment, further wherein the total weight of said solvent solubilizing polymeric segments are from about 40 to about 90 wt. % of the weight of said dispersant and the anchoring block has at least one functional imide group and is present from about 10 to about 60 wt. % of said dispersant.

3. The polymeric dispersant according to claim 1 , wherein D comprises 300 to 5000 g/mole number average molecular weight poly(alkylene oxide) and N is from 1 to 50.

4. The polymeric dispersant according to claim 3 , wherein D comprises a 500 to 3000 g/mole number average molecular weight poly(alkylene oxide), N is from 3 to 50, and said poly(alkylene oxide) comprises from 50 to 70 weight % of said dispersant.

5. The polymeric dispersant according to claim 1 , wherein D comprises a 300-5000 g/mole number average molecular weight polyester solvent solubilizing chain and N is from 1 to 50.

6. The polymeric dispersant according to claim 5 , wherein D comprises a 500 to 3000 g/mole number average molecular weight polyester derived from homo or co-polymerizing hydroxycarboxylic acids or lactones from said hydroxycarboxylic acid having 2 to 18 carbon atoms, N is from 3 to 50, and wherein 50 to 70 wt. % of said dispersant is said polyester.

7. The polymeric dispersant according to claim 1 , wherein D comprises a 300 to 5000 g/mole number average molecular weight polyolefin or polyacrylate and wherein N is from 1 to 50.

8. The polymeric dispersant according to claim 7 , wherein D comprises a 500 to 3000 g/mole number average molecular weight polyolefin or polyacrylate and wherein N is from 3 to 50.

9. The polymeric dispersant according to claim 1 , having a number average molecular weight from about 2000 to about 60,000 g/mole.

10. The polymeric dispersant according to claim 1 wherein K is from 2 to about 25.

11. The polymeric dispersant according to claim 1 , wherein the fused aromatic ring, of the imide having the carbonyl groups directly bonded to carbon atoms of a fused aromatic ring, comprises from 2 to 4 fused aromatic rings.

12. The polymeric dispersant according to claim 11 , wherein the fused aromatic ring comprises a naphthalene fused aromatic ring.

13. A composition comprising a particulate solid, water, a polar or a non-polar organic medium, and a polymeric dispersant having at least one imide pendant group where the carbonyl groups of the imide are directly bonded to carbon atoms of a fused aromatic ring, wherein the polymeric dispersant is represented by a polymeric dispersant of claim 1 .

14. The composition of claim 13 , wherein the composition is a millbase, paint or ink.

15. The composition of claim 13 , wherein the particulate solid is a pigment or filler.

16. The composition of claim 13 , further comprising a binder.

17. The composition of claim 13 , wherein the polymeric dispersant is present in an amount ranging from 0.5 wt. % to 30 wt. % of the composition.

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Shooter Andrew J
• Thetford Dean
• Jennings Robert A
• Richards Stuart N

Classifications

• C09D7/40

  Additives · CPC title

• C08F220/14 Primary

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C09D133/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C08F267/06

  on to polymers of esters · CPC title

• C08F220/1804 Primary

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title