Aromatic dispersant composition

Patent metadata

Field	Value
Publication number	US-10100152-B2
Application number	US-201615378468-A
Country	US
Kind code	B2
Filing date	Dec 14, 2016
Priority date	May 2, 2012
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

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, Cl, —Br, —NH 2 , or —OR′ wherein M is H, a metal cation, —NR′ 4 + , or mixtures thereof;
a is 1 or 2;
W is oxygen, sulphur, >NH, or >NG;
R′ is independently —H, or an optionally-substituted alkyl containing 1 to 20 carbon atoms, and the substituents is hydroxyl or halogen or mixtures thereof;
R 2 is a C 1 to C 20 hydrocarbylene group or a C 1 to C 20 hydrocarbonylene group, 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) a homopolymer chain of ethylene oxide, b) a copolymer chain of ethylene oxide, wherein the ethylene oxide constitutes 40 wt % to 99.99 wt % of the copolymer chain, or c) mixtures of polyester and said homopolymer of ethylene oxide or said copolymer chain of ethylene oxide;
u=1 to 3;
v=1 to 2;
w=1 to 3
v=2 when W=>NH;
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 claim 2 , wherein the Poly(ether) comprises 0 to 50 wt % propylene oxide, 50 to 100 wt % ethylene oxide.

4. The polymer of claim 1 is obtained/obtainable by a process comprising:
Step (1): reacting (i) amino acid, or (ii) an aminoalcohol, or (iii) an aminothiol, or (iv) a diamine,
with a naphthalene di-acid or anhydride or other acid-forming derivative (such as di-ester, di-amide, acid chloride) to form an acid-functionalised naphthalene imide or an hydroxyl-functionalised naphthalene imide, or a thiol-functionalised naphthalene imide, or an amino-functionalised naphthalene imide respectively;
Step (2): reacting the acid-functionalised naphthalene imide or the hydroxyl-functionalised naphthalene imide, or the thiol-functionalised naphthalene imide, or the amino-functionalised naphthalene imide with a polymer chain, or monomers that polymerise to form the polymer chain.

5. 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.

6. The polymer of claim 1 , wherein Q is based on a naphthalene anhydride selected from the group of 4-nitro-1,8-naphthalic imide (when one R 1 ═NO 2 ), 3-nitro-1,8-naphthalic imide (when one R 1 ═NO 2 ), 4-chloro-1,8-naphthalic imide (when one R 1 ═Cl), 3-sulpho-1,8-naphthalic imide (when one R 1 ═SO 3 H), or mixtures thereof.

7. The polymer of claim 1 , wherein the polymer chain is a poly(ether) represented by Formula (2):

wherein each variable is independently
R 1 is as described in claim 1 ;
a is 1 or 2;
W is oxygen;
R′ is independently —H, or an optionally-substituted alkyl containing 1 to 20 carbon atoms, 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, 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;
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;
with the proviso that when R 2 is a hydrocarbylene group, u is 1 and w is 1; and
m is 1 to 110.

8. 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 as described in claim 1 ;
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 carbon atoms, and the substituents is hydroxyl or halogen, or mixtures thereof;
R 2 is a C 1 to C 20 hydrocarbylene group or a C 1 to C 20 hydrocarbonylene group, 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.

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

wherein each variable is independently
R 1 is as described in claim 1 ;
a is 1 or 2;
W is nitrogen;
R′ is independently —H, or an optionally-substituted alkyl, typically, containing 1 to 20 carbon atoms, 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, the hydrocarbylene group or hydrocarbonylene group is linear or branched;
R 3 is H 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 su

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Shooter Andrew J
• Thetford Dean
• Richards Stuart N

Classifications

• C08G63/664 Primary

  derived from hydroxy carboxylic acids · CPC title

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title