Aromatic dispersant composition

Patent metadata

Field	Value
Publication number	US-9540486-B2
Application number	US-201314397203-A
Country	US
Kind code	B2
Filing date	Apr 25, 2013
Priority date	May 2, 2012
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

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 fused aromatic imide pendant group. The invention further provides compositions for coatings, inks, toners, plastic materials (such as thermoplastics), plasticizers, plastisols, crude grinding and flush.

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 represented by one or more of —H, or an electron withdrawing group chosen from a halogen, a nitrile, a nitro group, a sulphamoyl group, a sulphonate group, a hydroxy group, or an amino group;
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 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;
Pol is a homopolymer chain or a copolymer chain, wherein the polymer chain is selected from the group consisting essentially of a Poly(ether); of the structure (CH 2 —CH(R 4 )—O—) m and R 4 is methyl, ethyl or phenyl when Pol is a homopolymer, and R 4 is a mixture of H in an amount sufficient to provide ethylene oxide groups at 0 wt % to 60 wt % and at least one of methyl, ethyl and phenyl or mixtures thereof;
u is 1 to 3;
v is 1 to 2;
w is 1 to 3;
m is 1 to 110;
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
Q is a fused aromatic naphthalene ring 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 fused aromatic naphthalene di-acid or anhydride to form an acid-functionalised fused aromatic naphthalene imide or an hydroxyl-functionalised fused aromatic naphthalene imide, or a thiol-functionalised fused aromatic naphthalene imide, or an amino-functionalised fused aromatic naphthalene imide respectively;
Step (2): reacting the acid-functionalised fused aromatic naphthalene imide or the hydroxyl-functionalised fused aromatic naphthalene imide, or the thiol-functionalised fused aromatic naphthalene imide, or the amino-functionalised fused aromatic naphthalene imide with a polyether chain, or monomers that polymerise to form the polyether chain.

3. The polymer of claim 1 , which is obtained by a process comprising:
reacting a polyether amine with a naphthalene diacid or anhydride to form the product.

4. 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 a substituent in any position and R 1 is represented by one or more of —H, or an electron withdrawing group chosen from a halogen, a nitrile, a nitro group, a sulphamoyl group, a sulphonate group, a hydroxy group, or an amino group;
W is oxygen;
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 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 methyl, ethyl or phenyl when Pol is a homopolymer, and R 4 is a mixture of H in an amount sufficient to provide ethylene oxide groups at 0 wt % to 60 wt % and at least one of methyl, ethyl and phenyl or mixtures thereof;
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.

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 in any position and R 1 is represented by one or more of —H, or an electron withdrawing group chosen from a halogen, a nitrile, a nitro group, a sulphamoyl group, a sulphonate group, a hydroxy group, or an amino group;
W is sulphur, oxygen or >NG;
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 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 methyl, ethyl or phenyl when said polyether is a homopolymer, and R 4 is a mixture of H in an amount sufficient to provide ethylene oxide groups at 0 wt % to 60 wt and at least one of methyl, ethyl and phenyl or mixtures thereof;
u is 1 to 3;
w is 1 to 3; and
m is 1 to 110.

6. 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 a substituent in any position and R 1 is independently represented by one or more of an electron withdrawing group chosen from a halogen, a nitrile, a nitro group, a sulphamoyl group, a sulphonate group, a hydroxy group, or an amino group;
W is nitrogen;
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 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 methyl, ethyl or phenyl when said polyether is a homopolymer, and R 4 is a mixture of H (in an amount sufficient to provide ethylene

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Thetford Dean
• Shooter Andrew J
• Richards Stuart N

Classifications

• C08L23/36

  by reaction with nitrogen-containing compounds, e.g. by nitration · CPC title

• C08G65/3326 Primary

  aromatic · CPC title

• C08G2650/50

  containing nitrogen, e.g. polyetheramines or Jeffamines(r) · CPC title

• C08G59/22

  Di-epoxy compounds · CPC title

• C09B67/0089

  non ionic dispersing agent, e.g. EO or PO addition products · CPC title