Process for preparing urea urethane polymer

Patent metadata

Field	Value
Publication number	US-11795343-B2
Application number	US-201816762745-A
Country	US
Kind code	B2
Filing date	Nov 5, 2018
Priority date	Nov 14, 2017
Publication date	Oct 24, 2023
Grant date	Oct 24, 2023

Abstract

The presently claimed invention relates to a process for preparing urea urethane polymer, liquid compositions comprising the urea urethane polymer and the use of the urea urethane polymer as a thickening and thixotropic agent for water based and solvent based paint and coating formulations, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile and drilling muds plaster formulations, PVC plastisol and cement formulations.

First claim

The invention claimed is:

1. A process for preparing a urea urethane, the process comprising:
i) introducing toluene diisocyanate into a reactor;
ii) adding at least one monohydroxyl compound of formula (I)
R—OH  (I),

wherein R is linear or branched alkyl comprising 4 to 22 carbon atoms, linear or branched alkenyl comprising 4 to 22 carbon atoms, cycloalkyl comprising 6 to 12 carbon atoms, aralkyl comprising 7 to 12 carbon atoms, a radical of formula C m H 2m+1 (O—C n H 2n ) x —, a radical of formula C m H 2m+1 [O—C(═O)—C v H 2v ] x —, or a radical of formula C m H 2m+1 (O—C n H 2n ) x−1 [O—C(═O)—C v H 2v ] x —, wherein m is an integer from 1 to 22, n is an integer from 2 to 4, x is an integer from 1 to 15 and v is an integer from 4 to 6,
to obtain at least one monoisocyanate adduct;
whereby a molar ratio of the at least one monohydroxyl compound of formula (I) to the toluene diisocyanate is in a range of ≥1.05:1.0 to ≤1.2:1.0;
iii) preparing a pre-mix by mixing at least one diamine, at least one polar aprotic solvent, and at least one lithium salt; and
iv) feeding the pre-mix obtained in iii) into the reactor to react with the at least one monoisocyanate adduct obtained in ii), to obtain the urea urethane.

2. The process according to claim 1 , wherein the toluene diisocyanate is either 2,4-toluene diisocyanate or an isomeric mixture of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate.

3. The process according to claim 2 , wherein 2,4-toluene diisocyanate is present in the isomeric mixture in an amount in a range of ≥85.0 wt.-% to ≤99.9 wt.-%, based on a total weight of the isomeric mixture.

4. The process according to claim 2 , wherein 2,4-toluene diisocyanate is present in the isomeric mixture in an amount in a range of ≥90.0 wt.-% to ≤99.9 wt.-%, based on a total weight of the isomeric mixture.

5. The process according to claim 1 , wherein m is an integer from 1 to 4.

6. The process according to claim 1 , wherein n is 2.

7. The process according to claim 1 , wherein x is an integer from 3 to 10.

8. The process according to claim 1 , wherein the at least one monohydroxyl compound of formula (I) is selected from the group consisting of butyltriglycol, methoxy polyethylene glycol, butanol, isotridecyl alcohol, oleyl alcohol, a Guerbet alcohol containing 8 to 20 carbon atoms, linoleyl alcohol, lauryl alcohol, stearyl alcohol, cyclohexanol and benzyl alcohol.

9. The process according to claim 1 , wherein the molar ratio of the at least one monohydroxyl compound of formula (I) to the toluene diisocyanate is in a range of ≥1.1:1.0 to ≤1.2:1.0.

10. The process according to claim 1 , wherein the at least one monohydroxyl compound of formula (I) in (ii) is added during a time period in a range of ≥3 hours to ≤50 hours.

11. The process according to claim 1 , wherein, in (ii), a temperature is in a range of ≥20° C. to ≤60° C.

12. The process according to claim 1 , wherein the at least one diamine is selected from the group consisting of an amine of formula (II),
H 2 N—R′—NH 2   (II),

wherein R′ is —C y H 2y and y is an integer from 2 to 12,

an amine of formula (III),

an amine of formula (IV), and

and
an amine of formula (V),

wherein each R″ is independently CH 3 — or H.

13. The process according to claim 1 , wherein the at least one diamine is selected from the group consisting of 4,4-diamino-diphenylmethane, 3,3-dimethyl-4,4-diamino-diphenylmethane, 2,2-bis(4-aminocyclohexyl)-propane, N,N-dimethyl-4,4-diaminodiphenylmethane, (3-methyl-4-aminocylcohexyl)-(3-methyl-4-aminophenyl)-methane, isomeric xylylenediamine, ethylenediamine, hexamethylenediamine, 4,4-methylenebis(cyclohexylamine) and 1,12-diaminododecane.

14. The process according to claim 1 , wherein the at least one polar aprotic solvent is selected from the group consisting of dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, N-propylpyrrolidone, N-butylpyrrolidone, N,N,N′,N′-tetramethylurea, and hexamethyl-phosphoric acid triamide.

15. The process according to claim 1 , wherein the at least one lithium salt is selected from the group consisting of lithium chloride, lithium nitrate and lithium bromide.

16. The process according to claim 1 , wherein the at least one lithium salt is present in a range of ≥0.3 to ≤1.5 mole, relative to an equivalent weight of the at least one diamine.

17. The process according to claim 1 , wherein the urea urethane obtained has a weight average molecular weight in a range of ≥500 g/mol to ≤3000 g/mol determined according to DIN 55672-1.

18. The process according to claim 1 , wherein the at least one monohydroxyl compound is butyl triglycol.

19. The process according to claim 18 , wherein the diamine is m-xylylene diamine.

20. A liquid composition, comprising:
≥0.01 wt. % to ≤10.0 wt.-%, based on a total weight of the liquid composition, of a urea urethane obtained according to the process of claim 1 ; and
≥15.0 wt.-% to ≤99.9 wt.-%, based on the total weight of the liquid composition, of at least one member, selected from the group consisting of a pigment paste, a binder, a filler, a solvent, a defoamer, a neutralising agent, a wetting agent, a pigment dispersing agent, a preservative and water.

21. The liquid composition according to claim 20 , wherein the composition is a paint, water based coating formulation, solvent based coating formulation, lacquer, varnish, paper coating, wood coating, adhesive, ink, cosmetic formulation, detergent formulation, textile, or drilling muds plaster formulation, cement composition, plasterboard formulation, hydraulic binder formulation, ceramic formulation or leather formulation.

22. A method of producing a paint or coating formulation, adhesive, paint lacquer, PVC plastisol, or ink or cement formulation, the method comprising obtaining a urea urethane by the process according to claim 1 .

Assignees

• Basf Se

Inventors

• Kou Huiguang
• Tritschler Ulrich
• Peter Wolfgang
• Auschra Clemens

Classifications

• C09D175/12 Primary

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/225 Primary

  of alkali or alkaline earth metals · CPC title

• C08G18/282

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/283

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