Non-fused aromatic dispersant composition

Patent metadata

Field	Value
Publication number	US-10150838-B2
Application number	US-201414913102-A
Country	US
Kind code	B2
Filing date	Aug 12, 2014
Priority date	Aug 29, 2013
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

The present invention relates to a composition containing a particulate solid, a polar or non-polar organic medium, and a polymer chain having at least one non-fused aromatic imide pendant group. The invention further provides compositions for coatings, inks, toners, plastic materials (such as thermoplastics), plasticisers, plastisols, crude grinding and flush.

First claim

What is claimed is:

1. A polymer comprising a polymer chain having at least one non-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 represented by one or more electron withdrawing group chosen from —NO 2 , —SO 2 NR′ 2 , —C(O)R′, —SO 3 M, or a halo, —NH 2 , or —OR′;
a is 1 or 2 when R 1 is as described above or optionally a can be 4 when R 1 is chloro or bromo;
wherein M is a mono, di, or trivalent alkali, alkaline, or transition metal;
R′ is a —H, an optionally-substituted alkyl, and the substituent 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 or mixtures thereof;
R 3 is a 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 can optionally contain a group capable of polymerization;
Pol is a homopolymer chain or a copolymer chain, wherein the polymer chain is selected from the group consisting of a poly(ether), poly(ester), poly(ester amide), poly(amide), poly(alkylene), and mixtures thereof;
u is 1 to 3;
v is 1 to 2;
w is 1 to 3;
wherein W is nitrogen, oxygen, sulphur, or >NG;
v is 2 when W is nitrogen;
v is 1 when W is oxygen, sulphur, or >NG;
G is a hydrogen or a hydrocarbyl group containing 1 to 200 carbon atoms; and
Q is a non-fused aromatic ring containing 4n+2 π-electrons, wherein n=1 or more, 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 which is obtained by a process comprising:
Step (1): reacting (i) amino acid or (ii) an aminoalcohol, or (iii) an aminothiol, or (iv) a diamine or polyamine,
with a non-fused aromatic di-acid or anhydride or other acid-forming derivative to form an acid-functionalised non-fused aromatic imide or an hydroxyl-functionalised non-fused aromatic imide, or a thiol-functionalised non-fused aromatic imide, or an amino-functionalised non-fused aromatic imide respectively;
Step (2): reacting the acid-functionalised non-fused aromatic imide or the hydroxyl-functionalised non-fused aromatic imide, or the thiol-functionalised non-fused aromatic imide, or the amino-functionalised non-fused aromatic imide with a polymer chain, or monomers that polymerise to form the polymer chain.

3. The polymer of claim 2 , wherein the non-fused aromatic ring or non-fused aromatic di-acid or anhydride or other acid-forming derivative is based on a substituted phthalic anhydride.

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

5. The polymer of claim 1 , wherein Q is based on a phthalic anhydride including 4-nitro-phthalic anhydride or 3-nitro-phthalic anhydride, 4-chloro-phthalic anhydride or 3-chloro-phthalic anhydride, 4-sulpho-phthalic anhydride or 3-sulpho-phthalic anhydride, tetra-bromo phthalic anhydride, tetra-chloro phthalic anhydride, 3-bromo phthalic anhydride, 4-bromo phthalic anhydride, or mixtures thereof.

6. 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 represented by one or more an electron withdrawing group chosen from —NO 2 , —SO 2 NR′ 2 , —C(O)R′, —SO 3 M, or a halo, —NH 2 , or —OR′;
W is oxygen;
R′ is —H, an optionally-substituted alkyl, and the substituent 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 or mixtures thereof;
R 3 is a 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 can optionally contain a group capable of polymerization;
R 4 is H, methyl, ethyl or phenyl when Pol is a homopolymer, and when Pol is a copolymer R 4 is a mixture of H and at least one of methyl, ethyl and phenyl or mixtures thereof in an amount sufficient to provide ethylene oxide groups at 0 wt % to 99.9 wt %;
z is either 0 or 1;
a is 1 or 2 when R 1 is as described above or optionally a can be 4 when R 1 is chloro or bromo;
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.

7. 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 represented by one or more electron withdrawing group chosen from —NO 2 , —SO 2 NR′ 2 , —C(O)R′, —SO 3 M, or a halo, —NH 2 , or —OR′;
W is sulphur, oxygen or >NG;
R′ is —H, an optionally-substituted alkyl, and the substituent 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 or mixtures thereof;
G is a hydrocarbyl group containing 1 to 200 carbon atoms;
R 3 is a 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 can optionally contain a group capable of polymerization;
when Pol is a homopolymer, R 4 is methyl, ethyl or phenyl, and when Pol is a copolymer R 4 is a mixture of H and at least one of methyl, ethyl and phenyl or mixtures thereof in an amount sufficient to provide ethylene oxide groups at 0 wt % to 60 wt %;
z is either 0 or 1;
a is 1 or 2 when R 1 is as described above or optionally a can be 4 when R 1 is chloro or bromo;
u is 1 to 3;
w is 1 to 3; 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 (3b):

wherein each variable is independently
R 1 is independently represented by one or more electron withdrawing group chosen from —NO 2 , —SO 2 NR′ 2 , —C(O)R′, —SO 3 M, or a halo, —NH 2 , or —OR′;
W is nitrogen;
R′ is —H, an optionally-substituted alkyl, and the substituent 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 or mixtures thereof;
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 can optionally contain a group capable of polymerization;
when Pol is a homopolymer, R 4 is methyl, ethyl or phenyl, and when Pol is a copolymer, R 4 is a mixture of H and at least one of methyl, ethyl and phenyl, or mixtures thereof in an amount sufficient to provide ethylene oxide groups at 0 wt % to 60 wt %;
z is either 0 or 1;
a is 1 or 2 when

Assignees

• Lubrizol Advanced Mat Inc
• Lubrizol Advanced Mat Inc

Inventors

• Shooter Andrew J
• Thetford Dean

Classifications

• C08K5/3417

  condensed with carbocyclic rings · CPC title

• C09D11/03

  characterised by features other than the chemical nature of the binder · CPC title

• C09D7/45

  Anti-settling agents · CPC title

• C08G65/333 Primary

  containing nitrogen · CPC title

• C08G65/33341

  aromatic · CPC title