# US 8,772,435 B2 · Dispersants

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- Number: US 8,772,435 B2
- Document ID: US8772435B2
- Status: Granted
- Kind: B2
- Application number: 11/911,039
- Filed: 2006-04-07
- Published: 2008-07-10
- Granted: 2014-07-08
- Earliest claimed: 2005-04-13
- Assignees: Lubrizol Advanced Materials, Inc.
- Applicants: Neil L. Simpson; Dean Thetford
- Inventors: Neil L. Simpson; Dean Thetford
- Web page: https://patentgrep.com/patent/US8772435B2

## CPC

- C08G 73/0206: {Polyalkylene(poly)amines}
- C09B 67/0069: {Non aqueous dispersions of pigments containing only a solvent and a dispersing agent}
- C09B 67/009: {polymeric dispersing agent}
- C09D 7/45: Anti-settling agents
- C09D 11/03: characterised by features other than the chemical nature of the binder
- C09K 23/14: Derivatives of phosphoric acid
- C09K 23/16: Amines or polyamines
- C09K 23/28: Aminocarboxylic acids (proteins and protein hydrolysates C09K23/30)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to dispersants for dispersing a particulate solid for millbases, paints and inks. The present invention provides a composition containing a particulate solid, a polar organic medium and a compound or salts thereof for formula T-(A)m(B)n—X—Z-Q(0-p) wherein T is hydrogen or a polymerization terminating group; A is the residue of a hydroxy carboxylic acid or lactone thereof; B is the residue of an amino carboxylic acid; X is a direct bond or a divalent group; Z is an acidic or basic group or a moiety which contains an acidic or basic group; Q is an optional residue of an oxide, urea or a dibasic acid or anhydride thereof; m and n are positive integers; and p represents the number of residual amino and/or imino groups in Z.

## Claims

### Claim 1

A dispersant of formula 1:
T-(A)m(B)n—X—Z-Q(0-p) Formula (1)
including salts thereof
wherein
-(A)m(B)n— is the reaction product of at least one hydroxy carboxylic acid or lactone thereof and at least one amino carboxylic acid at 50 C to 250 C optionally in the presence of a esterification catalyst where m and n are as described below;
T is hydrogen or a polymerisation terminating group;
A is an oxyalkylene carbonyl residue of a hydroxy carboxylic acid or lactone thereof;
B is derived from said amino carboxylic acid;
X is a direct bond or a divalent linking group;
Z is a basic group of 1000 to 200,000 g/mole number average molecular weight selected from polyvinylamine or poly(C2-4-alkyleneimine) or a moiety which contains said basic group;
when Z is said polyvinylamine or poly(C2-4-alkyleneimine), Q is an oxygen atom of a N-oxide reaction product of amino or imino groups of Z reacted with oxygen or a peroxide, or a reaction product of said amino or imino groups reacted with dibasic acid or anhydride thereof;
m and n are non-zero positive integers
m+n is from 4 to 2000;
(0-p) means from the value 0 to the value p;
p represents the maximum available number of amino and/or imino groups in Z which does not carry the group T-(A)m(B)nX—;
when Z is a basic group selected from polyvinylamine or poly(C2-4-alkyleneimine) or a moiety which contains said basic group there may be more than one group T-(A)m(B)n—X— attached to Z and said more than one group may be chemically the same or different.

### Claim 2 (depends on 1)

A dispersant as claimed in claim 1 wherein T is a terminating group derived from a carboxylic acid R—COOH or alcohol R—OH wherein R is optionally substituted C1-50-hydrocarbyl and wherein Z is a basic group selected from poly(C2-4-alkyleneimine).

### Claim 3 (depends on 2)

A dispersant as claimed in claim 2 wherein R is optionally substituted alkyl which may be linear or branched.

### Claim 4 (depends on 2)

A dispersant as claimed in claim 2 wherein R contains one or more ether groups.

### Claim 5 (depends on 1)

A dispersant as claimed in claim 1 wherein A is derived from a hydroxy-C2-20-alkenylene carboxylic acid or a hydroxy-C1-20-alkylene carboxylic acid or lactone thereof.

### Claim 6 (depends on 5)

A dispersant as claimed in claim 5 wherein the lactone is ε-caprolactone.

### Claim 7 (depends on 1)

A dispersant as claimed in claim 1 wherein B is derived from an amino-C2-20-alkenylene carboxylic acid or an amino-C1-20-alkylene carboxylic acid.

### Claim 8 (depends on 7)

A dispersant as claimed in claim 7 wherein the amino-C1-20-alkylene carboxylic acid is 6-amino caproic acid, 4-aminobutyric acid, β-alanine or sarcosine.

### Claim 9 (depends on 1)

A dispersant as claimed in claim 1 wherein m+n is not greater than 20.

### Claim 10 (depends on 1)

A dispersant as claimed in claim 1 wherein the ratio of m:n is from 3:1 to 1:3.

### Claim 11 (depends on 1)

A dispersant as claimed in claim 1 which comprises a poly(C2-4-alkyleneimine) carrying at least two chains of formula 4:
T-(A)m(B)n— Formula (4)
wherein T, A, B, m and n are as defined in claim 1.

### Claim 12 (depends on 1)

A dispersant as claimed in claim 1 wherein the dispersant is represented by formula 5:
wherein
X-*-*-X represents polyvinylamine or poly(C2-4-alkyleneimine);
Y represents the chain T-(A)m-(B)n— which is linked via an amide and/or salt linkage;
T, A, B, m and n are as defined in claim 1; and
r is from 4 to 2000.

### Claim 13 (depends on 12)

A dispersant as claimed in claim 12 wherein the weight ratio of X-*-*-X to Y is from 20:1 to 5:1 and wherein X-*-*-X represents poly(C2-4-alkyleneimine).

### Claim 14 (depends on 12)

A dispersant as claimed in claim 12 wherein Y represents a chain residue of formula 7:
wherein
R is a C1-20 hydrocarbyl group;
R2 is hydrogen or C1-4-alkyl; and
R3 is an aliphatic or aromatic residue containing up to 10 carbon atoms which optionally contains a polyether residue derivable from propylene oxide and/or ethylene oxide.

### Claim 15 (depends on 1)

A dispersant as claimed in claim 1 derived from reacting a TPOAC acid of formula 2:
R—CO(A)m(B)n—OH Formula (2)
with poly(C2-4-alkyleneimine) at a temperature from 50 to 250° C. preferably in an inert atmosphere and wherein R is a C1-50-hydrocarbyl.

### Claim 16 (depends on 14)

A dispersant as claimed in claim 14 derived from reacting a compound of formula 8:
with polyvinylamine or poly(C2-4-alkyleneimine).

### Claim 17 (depends on 1)

A composition comprising a particulate solid and a dispersing agent as claimed in claim 1.

### Claim 18 (depends on 17)

A composition as claimed in claim 17 which further comprises an organic liquid.

### Claim 19 (depends on 18)

A composition according to claim 18, further comprising a film-forming binder resin and used as a millbase, paint, or ink.

### Claim 20 (depends on 19)

A composition as claimed in claim 19 wherein the organic liquid is a polar organic liquid.