Aromatic dispersant composition

Patent metadata

Field	Value
Publication number	US-9534123-B2
Application number	US-201314397206-A
Country	US
Kind code	B2
Filing date	Apr 24, 2013
Priority date	May 2, 2012
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

The present invention relates to a polymer, and a composition containing a particulate solid, an aqueous medium, and a polymer chain having at least one fused aromatic imide pendant group. The invention further provides compositions for millbases, dispersions, coatings and inks.

First claim

What is claimed is:

1. A polymer comprising a polymer chain having at least one fused aromatic imide pendant group, wherein the polymer is represented by formula (1):

wherein each variable is independently
R 1 is a substituent on Q ring in any position available for bonding to a substituent group and R 1 is independently represented by at least one electron withdrawing group selected from —CN, —NO 2 , —SO 2 NR′ 2 , SO 3 M, halo —NH 2 , or —OR′;
a is 1 or 2, or 1;
W is oxygen, sulphur, >NH, or >NG;
R′ is independently —H, or an optionally-substituted alkyl, and the substituents is hydroxyl or halo, or mixtures thereof;
R 2 is a C 1 to C 20 hydrocarbylene group or a C 1 to C 20 hydrocarbonylene group, when R 2 contains more than 2 carbon atoms, the hydrocarbylene group or hydrocarbonylene group is linear or branched;
R 3 is H or C 1-50 -optionally substituted hydrocarbyl group that bonds to a terminal oxygen atom of the polymer chain forming a terminal ether or terminal ester group and may or may not contain a group capable of polymerization such as a vinyl group, or C 1-50 -hydrocarbonyl group that bonds to the oxygen atom of the polymer chain forming a terminal ester group or terminal urethane group and may or may not contain a group capable of polymerization such as a vinyl group, and the substituent is halo, ether, ester, or mixtures thereof;
Pol is a homopolymer chain of ethylene oxide or a copolymer chain of ethylene oxide, wherein the ethylene oxide constitutes 40 wt % to 99.99 wt % of the copolymer chain and where in the polymer chain is selected from the group consisting a poly(ether), poly(ester) and mixtures thereof;
u=1 to 3;
v=1 to 2;
w=1 to 3
v=2 when W=>NG;
v=1 when W=Oxygen, Sulphur, or >NG;
G is a hydrocarbyl group containing 1 to 200 carbon atoms; and
Q is a fused aromatic ring containing 4n+2 π-electrons, wherein n=2, and Q is bonded to the imide group in such a way to form a 5 or 6 membered imide ring.

2. The polymer of claim 1 , wherein the polymer chain is a Poly(ether) of either (i) a polyethylene oxide homopolymer, or (ii) a copolymer of ethylene oxide with either propylene oxide, butylene oxide, styrene oxide or mixtures thereof.

3. The polymer of any preceding claim 1 is obtained by a process comprising:
Step (1): reacting (i) amino acid or (ii) an aminoalcohol, or (iii) an aminothiol, or (iv) a diamine,
with a fused aromatic di-acid or anhydride or other acid-forming derivative to form an acid-functionalised fused aromatic imide or an hydroxyl-functionalised fused aromatic imide, or a thiol-functionalised fused aromatic imide, or an amino-functionalised fused aromatic imide respectively;
Step (2): reacting the acid-functionalised fused aromatic imide or the hydroxyl-functionalised fused aromatic imide, or the thiol-functionalised fused aromatic imide, or the amino-functionalised fused aromatic imide with a polymer chain, or monomers that polymerise to form the polymer chain.

4. The polymer of claim 1 , wherein the fused aromatic ring or fused aromatic di-acid or anhydride or other acid-forming derivative is based on 1,8-naphthalene imide, or 1,2-naphthalene imide or mixtures thereof.

5. The polymer of claim 1 , wherein the polymer chain is a poly(ether) polymer chain represented by Formula (3a):

wherein each variable is independently
R 1 is a substituent on Q ring in any position available for bonding to a substituent group and R 1 is independently represented by at least one electron withdrawing group selected from —CN, —NO 2 , —SO 2 NR′ 2 , SO 3 M, halo —NH 2 , or —OR′;
a is 1 or 2;
W is oxygen, sulphur, or >NG;
R′ is independently —H, or an optionally-substituted alkyl, typically, containing 1 to 20, or 1 to 10 carbon atoms, and the substituents is hydroxyl or halo (typically Cl), or mixtures thereof;
R 2 is a C 1 to C 20 hydrocarbylene group or a C 1 to C 20 hydrocarbonylene group when R 2 contains more than 2 carbon atoms, the hydrocarbylene group or hydrocarbonylene group is linear or branched;
G is a hydrocarbyl group containing 1 to 200 carbon atoms;
R 3 is H or C 1-50 -optionally substituted hydrocarbyl group that bonds to a terminal oxygen atom of the polymer chain forming a terminal ether or terminal ester group and may or may not contain a group capable of polymerization such as a vinyl group, or C 1-50 -hydrocarbonyl group that bonds to the oxygen atom of the polymer chain forming a terminal ester group or terminal urethane group and may or may not contain a group capable of polymerization such as a vinyl group, and the substituent is halo, ether, ester, or mixtures thereof;
R 4 is H when Pol is a homopolymer, and R 4 is a mixture of H (in an amount sufficient to provide ethylene oxide groups at 40 wt % to 99.99 wt %) and at least one of methyl, ethyl and phenyl, when Pol is a copolymer;
u is 1 to 3;
w is 1 to 3; and
m is 1 to 110.

6. The polymer of claim 1 , wherein the electron withdrawing group is —Cl or —NO 2 or —SO 3 M, wherein M is H, a metal cation, —NR′ 4 + , or mixtures thereof.

7. A composition comprising a particulate solid (typically a pigment or filler), an aqueous medium, and a polymer chain having at least one fused aromatic imide pendant group, wherein the polymer is represented by a polymer of claim 1 .

8. The composition of claim 7 , wherein the composition is a millbase, paint or ink.

9. The composition of claim 1 , wherein the polymer is present in an amount ranging from 0.1 wt % to 79.6 wt of the composition.

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Shooter Andrew J
• Thetford Dean
• Richards Stuart N

Classifications

• C09B67/009

  polymeric dispersing agent · CPC title

• C09D11/102

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title

• C08G63/664 Primary

  derived from hydroxy carboxylic acids · CPC title

• C09D11/00 Primary

  Inks · CPC title