# US 10,308,836 B2 · Dispersants with multiple aromatic imide anchor groups

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- Number: US 10,308,836 B2
- Document ID: US10308836B2
- Status: Granted
- Kind: B2
- Application number: 15/032,792
- Filed: 2014-10-24
- Published: 2016-09-01
- Granted: 2019-06-04
- Earliest claimed: 2013-11-01
- Applicants: Lubrizol Advanced Materials, Inc.
- Inventors: Andrew J. Shooter; Dean Thetford; Robert A. Jennings; Stuart N. Richards
- Web page: https://patentgrep.com/patent/US10308836B2

## CPC

- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G 18/284: {Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids}
- C08G 18/285: {Nitrogen containing compounds}
- C08G 18/3206: {aliphatic}
- C08G 18/3215: {containing aromatic groups or benzoquinone groups}
- C08G 18/3275: {containing two hydroxy groups}
- C08G 18/3846: {containing imide groups (C08G18/3821 takes precedence)}
- C08G 18/5021: {having nitrogen}
- C08G 18/6438: {Polyimides or polyesterimides}
- 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}
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08G 18/7657: {containing two or more aromatic rings}
- C09D 7/45: Anti-settling agents
- C09D 11/037: characterised by the pigment
- C09D 11/102: containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D 11/322: Pigment inks
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## 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

### Claim 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):
wherein each variable is independently each time it occurs as follow:
R1 is a non-hydrogen substituent on Q ring and R1 is independently an electron withdrawing group selected from the group of —NO2, —SO2NR′2, —C(O)R′, —SO3M, halogen, —NH2, or —OR′, or an electron releasing alkyl group of 1 to 3 carbon atoms, the number of non-H substituted groups on Q is from 0 to 2; wherein M is H, a metal cation, NR′4+, or mixtures thereof; each R′ is independently —H or an optionally-substituted alkyl containing 1 to 20 carbon atoms, and the substituent of R′ 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 n is the number of aromatic rings, and Q is bonded to the imide group in such a way to form a 5 or 6 membered imide ring;
b is independently 1 or 2;
and when b is 1 the imide group is terminal and attached to the Pol by one chemical bond 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; wherein the 1 to 3 imide groups are optionally attached to R2 at different carbon atoms of R2,
R2 is a C1 to C20 hydrocarbylene group or a C1 to C20 hydrocarbonylene group or mixtures thereof; R2 optionally includes oxygen and/or nitrogen atoms wherein there is at least 2 carbon atoms per every oxygen or nitrogen of R2;
W′ is a nitrogen atom, an oxygen atom or a direct bond;
w is one or more;
Pol is a polyurethane comprising at least two urethane and/or urea linkages and at least one solvent-solubilizing chain selected from the group of polyether, polyolefin, polyester and polyacrylate; wherein said at least one of polyether, polyester, polyolefin and polyacrylate terminal chains have a number average molecular weight of 500-2000 g/mole; and wherein said at least one solvent-solubilizing chain is selected from pendant, terminal, and/or lateral side chains, or mixtures of said terminal and/or side chains and wherein the polyurethane is essentially linear and is derived from a polyisocyanate with an average isocyanate functionality between 1.9 and 2.1.

### Claim 2 (depends on 1)

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
and c) 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
wherein W′, R1, Q, a, b, d, and R2 are as previously defined.

### Claim 3 (depends on 2)

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

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

The polymer according to claim 1, wherein on average at least one R1 per polymer is a —SO3H, —Cl, —Br, —NO2 group.

### Claim 8 (depends on 1)

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.

### Claim 9 (depends on 1)

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
R1 and R2 are previously defined in as a hydrocarbylene group or hydrocarbonylene group, Q is as previously defined,
E is defined as —OH, —NH2, —N(H)—, or —CO2H.

### Claim 10 (depends on 1)

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.

### Claim 11 (depends on 1)

The polymer of claim 1, wherein said polymer has at least three pendant imide groups having the formula
attached to polyurethane backbone in at least four separate locations.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 12)

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

### Claim 14 (depends on 1)

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.

### Claim 15 (depends on 14)

The polymer of claim 14, wherein the polymer contains up to 30 imide groups of Formula
wherein R1, Q, R2, W′, d, b, and a are as previously defined.

### Claim 16 (depends on 15)

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.

### Claim 17 (depends on 15)

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

### Claim 18 (depends on 15)

The polymer according to claim 15; wherein Q is naphthalene.

### Claim 19 (depends on 15)

The polymer according to claim 15, wherein on average at least one R1 per polymer is a —SO3H, —Cl, —Br, —NO2 group.

### Claim 20 (depends on 15)

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.