Dispersants

• US 20100324206A1
• Filed: 12/03/2007
• Published: 12/23/2010
• Est. Priority Date: 12/04/2006
• 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., Richards, Stuart N.
• Granted Patent: US 8,859,675 B2
• Time in Patent Office: Days
• US Class Current: 524/590
• CPC Class Codes: C08G 18/0814 containing ammonium groups or groups forming them
• CPC Class Codes: C08G 18/0852 the solvents being organic
• CPC Class Codes: C08G 18/284 Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
• CPC Class Codes: C08G 18/2865 Compounds having only one primary or secondary amino group; Ammonia
• CPC Class Codes: C08G 18/3275 containing two hydroxy groups
• CPC Class Codes: C08G 18/4615 containing nitrogen
• CPC Class Codes: C08G 18/5024 containing primary and/or secondary amino groups
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures
• CPC Class Codes: C09D 17/002 in organic medium C09D17/003, C09D17/004 take precedence
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 7/45 Anti-settling agents
• CPC Class Codes: C09K 23/16 Amines or polyamines

Abstract

The present invention provides a non-aqueous composition containing a particulate solid, an organic medium and a polyurethane dispersant having laterally attached pendant groups with tertiary amine group(s), an essentially linear backbone and laterally attached solvent-solubilising side chains of a polyester or polyether including mixtures of such side chains.

Claims

1. A non-aqueous composition comprising a particulate solid, an organic medium and a polyurethane dispersant having an essentially linear backbone, laterally attached solvent-solubilising side chains of a polyester or polyether including mixtures of such side chains, and pendant side chains with tertiary amines.

2. The composition as claimed in claim 1 wherein said pendant side chains with tertiary amines are separated from said essentially linear backbone by at least one atom and said tertiary amines are at least partially quaternized.

3. The composition as claimed in claim 1, wherein said tertiary amines are separated from said essentially linear backbone by less than 20 atoms.

4. The composition of claim 1, wherein said tertiary amines are separated from said essentially linear backbone by 3 to 10 carbon atoms and at least 20 mole % of said tertiary amines are quaternized.

5. The composition of claim 1 wherein the solvent-solubilising side-chains comprise at least one polyether chain that is poly(C_2-4-alkylene oxide) containing less than 60% by weight ethylene oxide.

6. The composition of claim 1 wherein the solvent-solubilising side chains comprise at least one polyester chain that is obtainable or obtained from a hydroxy carboxylic acid or lactone thereof containing from 1 to 26 carbon atoms, including mixtures thereof.

7. The composition of claim 6 wherein the lactone is ε

-caprolactone or δ

-valerolactone or mixtures thereof.

8. The composition of claim 1 wherein the number-average molecular weight of the polyester or polyether side chain is from 300 to 10,000 Daltons.

9. The composition of claim 1 wherein the polyurethane dispersant additionally comprises from 10 to 180 milliequivalents for each 100 g dispersant of tertiary amine groups within said pendant side chains.

11. The composition of claim 1 wherein the total weight percentage of solvent-solubilising lateral side chains is not less than 5% based on the total weight of polyurethane dispersant.

12. The composition of claim 2, wherein the solvent-solubilising chains comprises at least one polyether chain that contains the residue of a compound of formula 1

13. The composition of claim 2, wherein the solvent solubilising chains comprise at least one polyether chain that contains the residue of a compound of formula 2

14. The composition of claim 2, wherein the solvent-solubilising chains comprise at least one polyether chain that contains the residue of a compound of formula 3

15. The composition of claim 2 wherein the laterally attached solvent-solubilising chains comprise at least one polyester side chain that is the residue of a compound of formula 6

R⁹O(OC-A-O)_mH  

 

6

wherein

R⁹ is C_1-50-hydrocarbyl group;

A is C_1-26-alkylene and/or C_2-26-alkenylene; and

m is from 5 to 150.

24. A non-aqueous millbase, paint or ink which comprises a film-forming resin and the composition of claim 1.

10. (canceled)

16. A polyurethane dispersant having an essentially linear backbone and laterally attached solvent-solubilising polyether chains of poly(C_2-4-alkylene oxide) which contains less than 60% by weight ethylene oxide relative to the poly(C_2-4-alkylene oxide) chain and from 10 to 180 milliequivalents for each 100 g dispersant of tertiary amine groups in pendant side chains wherein said tertiary amines are separated from said essentially linear backbone by 1 to 20 carbon atoms.

17. The polyurethane dispersant of claim 16 wherein the poly(C_2-4-alkylene oxide) chain is the residue of a polyether which contains one hydroxyl and one secondary amino group at one end of the polyether chain which reacts with isocyanates.

18. The polyurethane dispersant of claim 16 wherein the poly(C_2-4-alkylene oxide) chain is the residue of a polyether which contains two hydroxyl groups at one end of the polyether chain which react with isocyanates and which are separated by not less than 5 atoms.

19. The polyurethane dispersant of claim 16 which further comprises from 10 to 180 milliequivalents of pendant chains with a tertiary amine or hinder aromatic amine group, including salts or quaternized version thereof for each 100 g dispersant.

20. A polyurethane dispersant having an essentially linear backbone and laterally attached solvent-solubilising polyester side chains and from 10 to 180 milliequivalents for each 100 g dispersant of tertiary amine groups in pendant side chains wherein said tertiary amines are separated from said essentially linear backbone by 1 to 20 carbon atoms.

21. The polyurethane dispersant of claim 20, wherein said tertiary amines are separated from said essentially linear backbone by 3 to 10 carbon atoms.

22. The polyurethane dispersant of claim 20, wherein the polyester side chain is the residue of a polyester which contains two hydroxyl groups at one end of the polyester chain which react with isocyanates and which are separated by from 5 to 17 atoms.

23. The polyurethane dispersant of claim 20, further including at least one laterally attached solvent solubilising polyether chain of poly(C_2-4-alkylene oxide) which contains less than 60% by weight ethylene oxide relative to the poly(C_2-4-alkylene oxide) chain.

25. (canceled)

26. (canceled)

27. A process for making a polyurethane dispersant with a comb microstructure comprising reacting together;

a) one or more polyisocyanates having an average functionality of from 2.0 to 2.5;

b) one or more compounds having at least one polyester or polyether chain and at least two groups which react with isocyanates which are located at one end of the compound such-that the polyester or chain(s) is laterally disposed in relation to the polyurethane polymer backbone;

c) one or more compounds having a tertiary amino group of formula,