# US 11,299,580 B2 · Thixotropic rheology modifying agent compositions

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,299,580 B2
- Document ID: US11299580B2
- Status: Granted
- Kind: B2
- Application number: 16/981,191
- Filed: 2019-03-25
- Published: 2021-01-28
- Granted: 2022-04-12
- Earliest claimed: 2018-03-27
- Assignees: AdvanSix Resins & Chemicals LLC
- Applicants: AdvanSix Resins & Chemicals LLC
- Inventors: Edward Asirvatham; Jaime A. Flores-Vasquez; Karttikay Moudgil
- Web page: https://patentgrep.com/patent/US11299580B2

## CPC

- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08G 18/225: {of alkali or alkaline earth metals}
- C08G 18/282: {Alkanols, cycloalkanols or arylalkanols including terpenealcohols}
- C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds}
- C08G 18/2835: {having less than 5 ether groups}
- C08G 18/3228: {acyclic}
- C08G 18/324: {containing only one aromatic ring}
- C08G 18/8038: {with compounds of C08G18/3225}
- C08J 3/096: {Nitrogen containing compounds}
- C08K 5/3412: having one nitrogen atom in the ring
- C08L 75/02: Polyureas
- C08L 75/04: Polyurethanes
- C09D 5/04: Thixotropic paints
- C09D 7/45: Anti-settling agents
- C09D 7/47: Levelling agents
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## Abstract

Solvents that are suitable for use with polyurethane-polyurea based rheology modifying agents of the type which, in the past, have generally been formulated as solids or viscous liquids. The present solvents enable the rheology modifying agents to be prepared and formulated in a liquid or solution form more suited to prepare coating formulations that include polyurethane-polyurea based rheology modifying agents. The present solvents are N-alkyl substituted caprolactams, including N-methyl caprolactam, N-ethyl caprolactam, N-butyl caprolactam, and mixtures thereof, which are aprotic, non-toxic, have good solvency for polar groups such as those found in polyurethanes and polyureas, are thermally stable, and have high boiling points and low vapor pressure.

## Claims

### Claim 1

A rheology modifying agent composition, comprising:
at least one polyurethane-polyurea polymer, having the following formula:
where R1 and R4 are the same or different straight or branched alkyl radicals or alkenyl radicals of 4-22 carbon atoms containing polyether, polyester or polycarbonate substituted alkyl chains;
R2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
R3 is an aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group; and
a solvent including one or more caprolactam-derived solvents according to the general formula:
wherein R is a linear alkyl group of 1 or 2 unsubstituted carbons.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the solvent is present in an amount between 20 wt. % and 95 wt. % of a total weight of the composition.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the solvent is present in an amount between 40 wt. % and 80 wt. % of a total weight of the composition.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the solvent further includes N-butyl caprolactam present in an amount ranging from 1 wt. % to 10 wt. % of the total or combined weight of the solvent.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the polyurethane-polyurea polymer is synthesized from:
a diisocyanate having the following formula:
O═C═N—R2—N═C═O
where R2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
a diamine having the following formula:
H2N—R3—NH2
where R3 is C2-C12 aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group.

### Claim 6

A method for preparing a rheology modifying agent composition, the method comprising:
providing an isocyanate terminated urethane polymer, wherein providing the isocyanate terminated urethane polymer comprises:
adding a mono hydroxyl containing compound to an excess of a diisocyanate to form a mixture including the mono hydroxyl containing compound and the diisocyanate; and
stirring the mixture of the mono hydroxyl containing compound and the diisocyanate to form the isocyanate terminated urethane polymer; and
combining the isocyanate terminated urethane polymer with a diamine, a catalyst and a solvent to form a polyurethane-polyurea polymer, the solvent including one or more caprolactam-derived solvents according to the general formula:
wherein R is a linear alkyl group of 1 or 2 unsubstituted carbons.

### Claim 7 (depends on 6)

The method of claim 6, wherein combining the isocyanate terminated urethane polymer the diamine, the catalyst and the solvent comprises:
mixing together the diamine, the catalyst, and the solvent to form a solution; and
adding the isocyanate terminated urethane polymer to the solution.

### Claim 8 (depends on 7)

The method of claim 7, wherein mixing together the diamine, the catalyst, and the solvent to form a solution comprises heating the diamine, the catalyst, and the solvent.

### Claim 9 (depends on 6)

The method of claim 6, wherein adding the isocyanate terminated urethane polymer to the solution is done over at least one hour.

### Claim 10 (depends on 6)

The method of claim 6, further comprising removing the excess diisocyanate by vacuum distillation.

### Claim 11 (depends on 6)

The method of claim 6, wherein the diisocyanate has the following formula:
O═C═N—R2—N═C═O
where R2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
a diamine having the following formula:
H2N—R3—NH2
where R3 is C2-C12 aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group.

### Claim 12 (depends on 6)

The method of claim 6, wherein the catalyst includes lithium chloride.

### Claim 13 (depends on 6)

The method of claim 6, wherein the one or more caprolactam-derived solvents include N-methyl caprolactam and N-ethyl caprolactam.

### Claim 14 (depends on 6)

The method of claim 6, wherein the solvent further includes N-butyl caprolactam, the N-butyl caprolactam present in an amount ranging from 1 wt. % to 10 wt. % the total or combined weight of the solvent.

### Claim 15

An end-use composition comprising:
a varnish, a pigment paste, a sealant, a cosmetic, a ceramic, a lubricant, an ink, an adhesive, a PVC plastisol coating, an epoxy coating, or a coating based on unsaturated polyester resins; and
a rheology modifying agent composition, the rheology modifying composition comprising:
at least one polyurethane-polyurea polymer, having the following formula:
where R1 and R4 are the same or different straight or branched alkyl radicals or alkenyl radicals of 4-22 carbon atoms containing polyether, polyester or polycarbonate substituted alkyl chains;
R2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
R3 is an aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group; and
a solvent including one or more caprolactam-derived solvents according to the general formula:
wherein R is a linear alkyl group of 1 or 2 unsubstituted carbons.

### Claim 16 (depends on 15)

The end-use composition of claim 15, wherein the rheology modifying agent composition is present in amount from 0.1 wt. % to 5 wt. % of the total weight of the end-use composition.

### Claim 17 (depends on 15)

The end-use composition claim 15, wherein the end-use composition is thixotropic.

### Claim 18 (depends on 15)

The end-use composition of claim 15, wherein the solvent is present in an amount between 20 wt. % and 95 wt. % of a total weight of the rheology modifying composition.

### Claim 19 (depends on 15)

The end-use composition of claim 15, wherein the solvent further includes N-butyl caprolactam present in an amount ranging from 1 wt. % to 10 wt. % of the total or combined weight of the solvent of the rheology modifying composition.

### Claim 20 (depends on 15)

The end-use composition of claim 15, wherein the polyurethane-polyurea polymer of the rheology modifying composition is synthesized from:
a diisocyanate having the following formula:
O═C═N—R2—N═C═O
where R2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
a diamine having the following formula:
H2N—R3—NH2
where R3 is C2-C12 aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group.