Thixotropic rheology modifying agent compositions

Patent metadata

Field	Value
Publication number	US-11299580-B2
Application number	US-201916981191-A
Country	US
Kind code	B2
Filing date	Mar 25, 2019
Priority date	Mar 27, 2018
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

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.

First claim

The invention claimed is:

1. A rheology modifying agent composition, comprising:
at least one polyurethane-polyurea polymer, having the following formula:

where R 1 and R 4 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;
R 2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
R 3 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.

2. 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.

3. 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.

4. 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.

5. The composition of claim 1 , wherein the polyurethane-polyurea polymer is synthesized from:
a diisocyanate having the following formula:
O═C═N—R 2 —N═C═O

where R 2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and

a diamine having the following formula:
H 2 N—R 3 —NH 2

where R 3 is C 2 -C 12 aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group.

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.

7. 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.

8. 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.

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

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

11. The method of claim 6 , wherein the diisocyanate has the following formula:
O═C═N—R 2 —N═C═O

where R 2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
a diamine having the following formula:
H 2 N—R 3 —NH 2

where R 3 is C 2 -C 12 aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group.

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

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

14. 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.

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 R 1 and R 4 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;
R 2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and
R 3 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.

16. 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.

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

18. 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.

19. 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.

20. 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—R 2 —N═C═O

where R 2 is an aliphatic, cycloaliphatic, aromatic, and/or alkyl substituted aromatic group; and

a diamine having the following formula:
H 2 N—R 3 —NH 2

where R 3 is C 2 -C 12 aliphatic straight chain or branched, cycloaliphatic, and/or alkyl substituted aromatic group.

Assignees

• Advansix Resins & Chemicals Llc

Inventors

• Asirvatham Edward
• Flores-Vasquez Jaime A
• Moudgil Karttikay

Classifications

• C08K5/3412

  having one nitrogen atom in the ring · CPC title

• C08G18/3228

  acyclic · CPC title

• C08L75/02

  Polyureas · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title

• C08G18/225

  of alkali or alkaline earth metals · CPC title