Dispersants with multiple aromatic imide anchor groups

• US 10,442,884 B2
• Filed: 04/28/2016
• Issued: 10/15/2019
• Est. Priority Date: 11/01/2013
• Status: Active Grant

• Current Assignee: Lubrizol Advanced Materials Incorporated (Berkshire Hathaway Incorporated)
• Original Assignee: Lubrizol Advanced Materials Incorporated (Berkshire Hathaway Incorporated)
• Inventors: Shooter, Andrew J., Thetford, Dean, Richards, Stuart N, Jennings, Robert A.
• Primary Examiner(s): Leonard, Michael L
• Application Number:
  US15/140,564
• Publication Number:
  US 20160237196A1
• Time in Patent Office: 1,265 Days
• CPC Class Codes: C08G 18/025 the polymeric products containing carbodiimide groups
• CPC Class Codes: C08G 18/284 Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
• CPC Class Codes: C08G 18/285 Nitrogen containing compounds
• CPC Class Codes: C08G 18/3846 containing imide groups C08G18/3821 takes precedence
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/6438 Polyimides or polyesterimides
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 18/794 formed by oligomerisation of aromatic isocyanates or isothiocyanates
• CPC Class Codes: C08L 79/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: C09D 11/10 based on artificial resins
• CPC Class Codes: C09D 11/102 containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C09D 11/322 Pigment inks
• CPC Class Codes: C09D 11/326 characterised by the pigment dispersant
• CPC Class Codes: C09D 179/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Abstract

A polyurethane dispersant is described that comprises a reaction product of a polyisocyanate with a) a component supplying a anchoring imide group wherein the carbonyl groups of the imide are bonded to a fused or non-fused aromatic ring, b) at least one solvent-solubilizing chain, and other optional components to build molecular weight or modify the interaction of the dispersant with various particulates or continuous media.

Claims

1. A polymer comprising a polymer chain having at least three imide groups, wherein each imide group is chemically bonded to an aromatic ring, the polymer is represented by Formula (1):

2. The polymer of claim 1 which is obtained by a process comprising:

a) sourcing a polyisocyanate molecule having at least three reactive isocyanate groups,

b) reacting at least one of said reactive isocyanate groups of said polyisocyanate molecule with at least one polyether, polyester, polyolefin and polyacrylate to form a terminal chain,

c) reacting at least one of said reactive isocyanate groups of said polyisocyanate with an imide group containing molecule of the formula

3. The polymer of claim 2, wherein the polymer contains up to 30 imide groups of formula

4. The polymer according to claim 2, wherein an optional additional modifier is reacted with up to 10 mol % of reactive isocyanate groups of said polyisocyanate.

5. The polymer according to claim 2, wherein said polyisocyanate molecule having at least three reactive isocyanate groups is selected from a commercially available polyisocyanate, a dimerized or trimerized polyisocyanate;

a diisocyanate and/or polyisocyanate reacted with a polyol, polyamine or amino alcohol having two or more groups reactive with isocyanate groups.

6. The polymer of claim 1, wherein said Q group is a single benzene ring or a naphthalene ring.

7. The polymer of any of claim 1, wherein said at least one of polyether, polyester, polyolefin and polyacrylate has at least one chemical group that is reactive with isocyanate groups to form a chemical bond at one end of the molecule but does not have a second distally located chemical group that is reactive with isocyanate groups to form a chemical bond and therefore creates a polyether, polyester, polyolefin or polyacrylate that is only attached to the polymer at one point and any additional ends of said polyether, polyester, polyolefin or polyacrylate function as a chain end.

8. The polymer of claim 1, wherein said polyether, polyester, polyolefin or polyacrylate used in said Pol comprise from about 20 to about 80 wt. % of said polymer.

9. The polymer of claim 1, wherein said polymer has at least two three imide groups having the formula

10. The polymer of claim 1, wherein said

11. The polymer according to claim 1, wherein Q is naphthalene.

12. The polymer according to claim 1, wherein on average at least one R₁ per polymer is a SO₃H, —

Cl, —

Br, —

NO₂ group.

13. A composition comprising a) a particulate solid, b) a medium comprising a polar organic or a nonpolar organic medium, or an aqueous medium, and c) a polymer represented by claim 1.

14. The composition of claim 13, wherein the composition is a millbase, paint or ink.

15. A composition comprising a polymer chain having at least one terminal imide group said imide groups being chemically bound to an aromatic group or a fused aromatic group, wherein the polymer is represented by claim 1, a particulate solid, and (i) a polar organic medium, (ii) a non-polar organic medium, (iii) water, or blends thereof.