Polymeric pigment dispersant having an acrylic backbone, polyester side chains, cyclic imide groups and quaternary ammonium groups

• US 6,037,414 A
• Filed: 09/02/1998
• Issued: 03/14/2000
• Est. Priority Date: 09/02/1998
• Status: Expired due to Term

• Current Assignee: Axalta Coating Systems Ip Co Llc (Axalta Coating Systems Ltd.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Sorser, Aleksandr, Simms, John A.
• Primary Examiner(s): Short, Patricia A.
• Application Number:
  US09/145,656
• Time in Patent Office: 559 Days
• Field of Search: 525/176, 525/186, 525/187, 525/327.3, 525/375, 525/378, 525/386, 524/504, 523/522
• US Class Current: 525/176
• CPC Class Codes: C01P 2006/22 Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
• CPC Class Codes: C08G 81/027 containing polyester or polycarbonate sequences
• CPC Class Codes: C09C 1/56 Treatment of carbon black ; Purification

Abstract

A polymeric pigment dispersant of a graft polymer having an acrylic polymer backbone and pending from the backbone, polyester side chains, cyclic imide groups and quaternary ammonium groups and the polymer having a calculated number average molecular weight of 8,000-50,000; wherein the graft copolymer is composed of

(a) 10-50%, by weight of the of the graft polymer, of an acrylic copolymer backbone having a number average molecular weight of 2500-10,000 which, before reaction, contains 25-75% by weight of polymerized oxirane containing monomers;

(b) 20-85%, by weight of the graft polymer, of a polyester copolymer, or mixture of different polyester copolymers, having a number average molecular weight of 500-10,000 which polyester copolymer is carboxylic-acid functional and is attached to the backbone by a reaction of the carboxylic acid functional group with oxirane group of the backbone;

(c) 1-16%, by weight of the graft polymer, of cyclic imide groups attached to the backbone by a reaction of the imide group with the oxirane group of the backbone and

(d) 0.2-17%, by weight of the graft polymer, of quaternary ammonium groups.

Claims

1. A polymeric pigment dispersant comprising a graft polymer having an acrylic polymer backbone and pending from the backbone, polyester side chains, cyclic imide groups and quaternary ammonium groups and the polymer having a calculated number average molecular weight of 8,000-50,000;

wherein the graft copolymer consists essentially of

(a) 10-50%, by weight of the of the graft polymer, of an acrylic copolymer backbone having a number average molecular weight of 2,500-10,000 which, before reaction, contains 25-75% by weight of polymerized oxirane containing monomers;

(b) 20-85%, by weight of the graft polymer, of a polyester copolymer, or mixture of different polyester copolymers, having a number average molecular weight of 500-10,000 which polyester copolymer is carboxylic-acid functional and attached to the backbone by a reaction of the carboxylic acid functional groups with oxirane groups of the backbone;

(c) 1-16%, by weight of the graft polymer, of cyclic imide groups attached to the backbone by a reaction on the imide groups with the oxirane groups of the backbone and

(d) 0.2-17%, by weight of the graft polymer, of quaternary ammonium groups.

2. The dispersant of claim 1, further comprising a mixture of a hydroxy functional polyester copolymer and a second non hydroxy functional polyester copolymer.

3. The dispersant of claim 1 wherein the oxirane containing monomers of the acrylic copolymer backbone comprises either glycidyl acrylate or glycidyl methacrylate.

4. The dispersant of claim 3, further comprising hydroxy functionality on said acrylic copolymer.

5. The dispersant of claim 1 wherein said polyester copolymer comprises polymerized monomeric units of a lactone.

6. The dispersant of claim 1 wherein said polyester copolymer comprises monomeric units of a saturated or unsaturated fatty acid or a hydroxy-functional aliphatic acid.

7. The dispersant of claim 2 wherein the hydroxy functional polyester copolymer is the esterification product of caprolactone and a hydroxy functional aliphatic acid and the second polyester copolymer the esterification product of caprolactone and saturated aliphatic carboxylic acid and an unsaturated carboxylic acid.

8. The dispersant of claim 1 in which the polyester copolymer is the esterification product of lauric acid and caprolactone.

9. The dispersant of claim 1 wherein the polyester is the reaction product of a mixture comprising cyclic anhydride containing monomers, epoxy containing monomers, and lactone containing monomers.

10. The dispersant of claim 1, wherein said cyclic imide is selected from the group consisting of phthalimide, saccharine, and maleimide, or mixtures thereof.

11. The dispersant of claim 1 wherein the quaternary ammonium groups is formed by reacting a tertiary amine containing carboxyl functionality with the oxirane group of the backbone and forming a quaternary ammonium group by reacting with aryl halide, aromatic sulfonate, alkyl sulfate or an alkane sultone.

12. The dispersant of claim 1 wherein the quaternary ammonium group is formed by reacting a compound having a quaternary ammonium group and carboxyl functionality with the oxirane group of the backbone.

13. The dispersant of claim 1 wherein the quaternary ammonium group is form by reacting a secondary amine with the oxirane group of the backbone and forming a quaternary ammonium group by reacting with benzyl chloride, aromatic sulfonate, alkyl sulfate or an alkane sultone.

14. A dispersion of a pigment using the pigment dispersant of claim 1.

15. A method of making a dispersant comprised of a graft polymer having a calculated number average molecular weight of 8,000-50,000 and having an acrylic polymer backbone and pending from the backbone, polyester side chains, cyclic imide groups and quaternary ammonium groups comprising simultaneously reacting:

(a) 10-50%, by weight of the of the graft polymer, of an acrylic copolymer backbone having a number average molecular weight of 2,500-10,000 which, before reaction, contains 25-75% by weight of polymerized oxirane containing monomers;

(b) 20-85%, by weight of the graft polymer, of a polyester copolymer, or mixture of different polyester copolymers, having a number average molecular weight of 500 to 10,000 which polyester copolymer is carboxylic-acid functional;

(c) 1-16%, by weight of the graft polymer, of cyclic imide groups and

(d) 0.2-17%, by weight of the graft polymer, of a precursor of a quaternary ammonium group and subsequently quaternizing said precursor to form quaternary ammonium group.