Dispersants with multiple aromatic imide anchor groups

Patent metadata

Field	Value
Publication number	US-2016237196-A1
Application number	US-201615140564-A
Country	US
Kind code	A1
Filing date	Apr 28, 2016
Priority date	Nov 1, 2013
Publication date	Aug 18, 2016
Grant date	—

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-solubilising chain, and other optional components to build molecular weight or modify the interaction of the dispersant with various particulates or continuous media.

First claim

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

wherein each variable is independently
R 1 may be a non-hydrogen substituent on Q ring in any position available for bonding to a substituent group and R 1 may be independently represented by one or more of —H, or an electron withdrawing selected from the group —NO 2 , SO 2 NR′ 2 , —C(O)R′, —SO 3 M, halo, —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 may be 0 to 2; wherein M can be H, a metal cation, NR′ 4 + , or mixtures thereof; R′ can be —H, an optionally-substituted alkyl typically containing 1 to 20, and the substituent of R′ may be hydroxyl or halo or mixtures thereof;
Q may be a fused or non-fused aromatic ring containing 4n+2 π-electrons, wherein n=1 or more, and Q may be 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; this means that there is the possibility of 1 to 3 imide groups attached to R 2 at different carbon atoms of R 2 ;
R 2 may be a C 1 to C 20 hydrocarbylene group or a C 1 to C 20 hydrocarbonylene group or mixtures thereof; R 2 may include oxygen and/or nitrogen atoms wherein there is at least 2 carbon atoms per every oxygen or nitrogen of R 2 , these would include ether, ester, and amide type linkages in R 2 ;
W′ is a nitrogen atom, an oxygen atom or a direct bond; when b is 2 then one of the W′ can be 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 can be 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; and
w is 1 or more.

2 . The polymer of claim 1 which is obtained/obtainable by a process comprising:
a) sourcing a polyisocyanate molecule having at least three reactive isocyanate groups, said polyisocyanate molecule serving as a building block for said Pol and as a source of isocyanate groups to form urethane and/or urea linkages when reacted with a hydroxyl or amino group containing species
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 , a, are as previously defined; to attach said imide groups to said Pol, W may be any group capable of reaction with an isocyanate group for example amino, hydroxyl, carboxylic acid,
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 (e.g. diol, triol, tetrols, amino alcohol, diamine, triamine, etc.).

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 (i.e. a chemical group in the molecule more than 17 consecutive backbone atoms from said first reactive group in the polyether, polyester, polyolefin and polyacrylate) 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 solvent-solubilising polyether, polyester, polyolefin or polyacrylate used in said Pol has a number molecular weight from about 300 to about 5000 g/mole.

9 . 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.

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

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

11 . 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 .

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

13 . 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.

14 . 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 .

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

16 . 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 (typically a pigment or filler), 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

• C08G18/285

  Nitrogen containing compounds · CPC title

• C08G18/4277

  Caprolactone and/or substituted caprolactone · CPC title

• C09D11/322

  Pigment inks · CPC title

• C08G18/025 Primary

  the polymeric products containing carbodiimide groups · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title