Dispersants with multiple aromatic imide anchor groups

• US 10,308,836 B2
• Filed: 10/24/2014
• Issued: 06/04/2019
• 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, Jennings, Robert A., Richards, Stuart N.
• Primary Examiner(s): Leonard, Michael L
• Application Number:
  US15/032,792
• Publication Number:
  US 20160251523A1
• Time in Patent Office: 1,684 Days
• 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 18/3206 aliphatic
• CPC Class Codes: C08G 18/3215 containing aromatic groups or benzoquinone groups
• CPC Class Codes: C08G 18/3275 containing two hydroxy groups
• CPC Class Codes: C08G 18/3846 containing imide groups C08G18/3821 takes precedence
• CPC Class Codes: C08G 18/5021 having nitrogen
• CPC Class Codes: C08G 18/6438 Polyimides or polyesterimides
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures
• CPC Class Codes: C08G 18/7657 containing two or more aromatic rings
• CPC Class Codes: C09D 11/037 characterised by the pigment
• 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 179/08 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C09D 7/45 Anti-settling agents

Abstract

Polymeric dispersants are disclosed that include a urethane backbone at least one pendantly attached imide group, wherein the carbonyl of the imide are chemically bonded to a single or fused aromatic ring. The aromatic ring can be substituted with various electron withdrawing or releasing groups. The dispersant also includes solvent-solubilizing chains of polyether, polyester, polyacrylate, and or polyolefin Desirably, the imide groups are derived from an imide that has two isocyanate reactive groups such that the imide is attached to the urethane backbone at two separate locations.

Claims

1. A polymer comprising a polymer chain having at least two urethane linkages and at least two pendant imide side chain 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 wherein said polymer comprises an essentially linear polyurethane backbone from reacting polyisocyanates with an average functionality between 1.9 and 2.1 with both

a) solvent-solubilising chains of polyether, polyolefin, polyester, and/or polyacrylic having two reactive groups, said reactive groups being reactive with isocyanates to form chemical bonds, at one end of said solvent-solubilising chain and said reactive groups being within 2 to 17 atoms of each other along the solvent-solubilising chain and

b) at least one imide compound having groups reactive with isocyanates, wherein the imide compound has an average functionality of 1.5 to 2.1 when reacted with isocyanates, wherein the polyurethane backbone has attached thereto 2 or more pendant imide side chains of the structure

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

4. The polymer according to claim 3, wherein said additional urethane formative compounds are reacted with up to 10 mol % of reactive isocyanate groups of said polyisocyanate.

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

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

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

SO₃H, —

Cl, —

Br, —

NO₂ group.

8. The polymer of claim 1, wherein said at least one of polyether, polyester, polyolefin and polyacrylate has at least two functional groups that are reactive with isocyanate groups to form a chemical bond at one end of the molecule but do 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.

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

a) sourcing a polyisocyanate molecule having isocyanate groups and an isocyanate functionality between 1.9 and 2.1 groups,

b) reacting at least one of said isocyanate groups of said polyisocyanate molecule with at least one solvent-solubilising chain selected from polyether, polyester, polyolefin and polyacrylate having about two groups at one end of said solvent-solubilising chain to form a terminal or pendant side chain,

c) reacting at least one of said reactive isocyanate groups of said polyisocyanate with an imide group containing molecule of the Formulas 7-11

10. 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.

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

12. A composition comprising a a) particulate solid, b) an aqueous medium, and c) a polymer represented by claim 1.

13. The composition of any claim 12, wherein the composition is a millbase, paint or ink.

14. A polymer according to claim 1, wherein the polymer comprises:

an essentially linear polyurethane backbone from reacting polyisocyanates with an average functionality between 1.9 and 2.1 with at least two imide compounds have groups reactive with isocyanates, wherein the imide compound has an average functionality of 1.5 to 2.1 when reacted with isocyanates, wherein the polyurethane backbone has attached thereto at least two pendant imide side chains and at least one terminally attached solvent-solubilising chains of polyether, polyolefin, polyester, and/or polyacrylic;

wherein at least 50 mole % of said solvent-solubilising chains of polyether, polyolefin, polyester, and/or polyacrylic have only one functional group reactive with isocyanate groups to form a chemical bond, at one end of said at least one solvent-solubilising chain and not having an isocyanate reactive group at the other terminus of said chain; and

said polyisocyanates are reacted with urethane formative compounds having groups reactive with isocyanates wherein the urethane formative compounds have an average functionality of 1.0 to 2.1.

15. The polymer of claim 14, wherein the polymer contains up to 30 imide groups of Formula

16. The polymer according to claim 15, wherein said additional urethane formative compound is reacted with up to 10 mol % of reactive isocyanate groups of said polyisocyanate.

17. The polymer of claim 15, wherein said Q group is a single benzene ring or a naphthalene ring.

18. The polymer according to claim 15;

wherein Q is naphthalene.

19. The polymer according to claim 15, wherein on average at least one R₁ per polymer is a —

SO₃H, —

Cl, —

Br, —

NO₂ group.

20. The polymer of claim 15, wherein at least 50 mole % of said solvent-solubilising chains selected from least one of polyether, polyester, polyolefin and polyacrylate has one functional group that is reactive with isocyanate groups to form a chemical bond at one end of the molecule but do 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.