Dispersants with multiple aromatic imide anchor groups

Patent metadata

Field	Value
Publication number	US-10442884-B2
Application number	US-201615140564-A
Country	US
Kind code	B2
Filing date	Apr 28, 2016
Priority date	Nov 1, 2013
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

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.

First claim

What is claimed is:

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):

wherein each variable is independently
R 1 is a non-hydrogen substituent and R 1 is independently represented by one or more of an electron withdrawing selected from the group —NO 2 , —SO 2 NR′ 2 , —C(O)R′, —SO 3 M, halogen, —NH 2 , and OR′, or an electron releasing alkyl group of 1 to 3 carbon atoms, the number of non-H substituted groups on Q defined by a is from 0 to 2; wherein M is H, a metal cation, NR′ 4 + , or mixtures thereof; R′ is H or an optionally-substituted alkyl typically containing 1 to 20, and the optional substituent of R′, when present, is hydroxyl or halogen or mixtures thereof;
Q is a fused or non-fused aromatic ring containing 4n+2 π-electrons, wherein n=1 or more, and Q is bonded to the imide group in such a way to form a 5 or 6 membered imide ring;
b is 1 or 2, and when b is 2 the imide group is a side chain attached to Pol by two chemical bonds;
d is 1, 2, or 3; and the imide groups are optionally attached to R 2 at different carbon atoms of R 2 ;
R 2 is a C 1 to C 20 hydrocarbylene group or a C 1 to C 20 hydrocarbonylene group or mixtures thereof; R 2 optionally includes oxygen and/or nitrogen atoms wherein there is at least 2 carbon atoms per every oxygen or nitrogen of R 2 ;
W′ is a nitrogen atom, an oxygen atom or a direct bond; when b is 2 then one of the W′ is derived from a secondary amine reacted with said isocyanate and be in the R 2 linking group between the imide and the other W′ group, when b is 2, each W′ group is the same or different;
Pol is a polyurethane comprising at least two urethane and/or urea linkages and at least one of polyether, polyester, polyolefin and polyacrylate terminal chains, or mixtures of said terminal chains; wherein said at least one of polyether, polyester, polyolefin and polyacrylate terminal chains have a number average molecular weight of 700-4000 g/mole; wherein said polyurethane is from a polyisocyanate having isocyanate functionality of three or more, and
w is 1 or more.

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

wherein b is 1 or 2 and d is 1, 2 or 3; and R 1 , Q, R 2 , and a, are as previously defined; to attach said imide groups to said Pol, W is any group capable of reaction with an isocyanate group,
c) optionally reacting said reactive isocyanate groups of said polyisocyanate molecule with at least one difunctional or higher crosslinking agent to couple multiple isocyanate groups into a single Pol,
d) optionally reacting said reactive isocyanate groups of said polyisocyanate molecule with at least one modifier for said Pol.

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

attached to Pol at least two separate locations on said Pol.

10. The polymer of claim 1 , wherein said

is derived from a reactant of the structure

wherein R 1 , R 2 , Q, d, b, and a are as previously defined in claim 1 .

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

12. The polymer according to claim 1 , wherein on average at least one R 1 per polymer is a SO 3 H, —Cl, —Br, —NO 2 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.

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Shooter Andrew J
• Thetford Dean
• Richards Stuart N
• Jennings Robert A

Classifications

• C09D11/326

  characterised by the pigment dispersant · CPC title

• C08G18/794

  formed by oligomerisation of aromatic isocyanates or isothiocyanates · CPC title

• C09D11/10

  based on artificial resins · CPC title

• C08G18/285

  Nitrogen containing compounds · CPC title

• C09D11/102

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title