Process for preparing a polyoxyalkylene carbonate polyol

Patent metadata

Field	Value
Publication number	US-12384869-B2
Application number	US-202117912606-A
Country	US
Kind code	B2
Filing date	Mar 26, 2021
Priority date	Apr 2, 2020
Publication date	Aug 12, 2025
Grant date	Aug 12, 2025

Abstract

The invention relates to a process for preparing a polyoxyalkylene carbonate polyol by reacting a polyoxyalkylene polyol with a cyclic carbonate in the presence of an amine catalyst. The invention further relates to polyoxyalkylene carbonate polyols obtainable using the method according to the invention and to a process for preparing polyurethanes by reacting the polyoxyalkylene carbonate polyols according to the invention with polyisocyanates.

First claim

The invention claimed is:

1. A process for preparing a polyoxyalkylenecarbonate polyol comprising reacting a polyoxyalkylene polyol with a cyclic carbonate in the presence of an amine catalyst.

2. The process as claimed in claim 1 , wherein the number-average molar mass of the polyoxyalkylene polyol is ≥200 g/mol as determined by means of gel permeation chromatography (GPC).

3. The process as claimed in claim 1 , wherein the molar ratio between cyclic carbonate and the hydroxyl end groups of the polyoxyalkylene polyol is from 1:1 to 20:1.

4. The process as claimed in claim 1 , wherein the polyoxyalkylenecarbonate polyol is prepared in the absence of any alkylene oxide.

5. The process as claimed in claim 1 , wherein the cyclic carbonate is selected from the group consisting of 4-methyl-1,3-dioxolan-2-one, 1,3-dioxolan-2-one, 1,3-dioxan-2-one, 5,5-dimethyl-1,3-dioxan-2-one, and mixtures thereof.

6. The process as claimed in claim 1 , wherein the amine catalyst is selected from the group consisting of trimethylamine, triethylenediamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triphenylamine, dimethylethylamine, N,N-dimethylcyclohexylamine, tetramethylenediamine, 1-methyl-4-dimethylaminoethylpiperazine, triethylamine, tripropylamine, tributylamine, dimethylbutylamine, N,N-dimethylbenzylamine, N,N-dimethylcyclohexylamine, N,N′,N″-tris(dimethylaminopropyl) hexahydrotriazine, dimethylaminopropylformamide, N,N,N′,N′-tetramethylethylenediamine, N,N,N′,N′-tetramethylbutanediamine, tetramethylhexanediamine, pentamethyldiethylenetriamine, tetramethyldiaminoethyl ether, dimethylpiperazine, 1,2-dimethylimidazole, 1-azabicyclo[3.3.0]octane, bis(dimethylaminopropyl) urea, bis(dimethylaminoethyl) ether, N-methylmorpholine, N-ethylmorpholine, N-cyclohexylmorpholine, 2,3-dimethyl-3,4,5,6-tetrahydropyrimidine, triethanolamine, diethanolamine, triisopropanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, dimethylethanolamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 1,4-diazabicyclo[2.2.2]octane (DABCO), imidazole, 1-methylimidazole, 2-methylimidazole, 4 (5)-methylimidazole, 2,4 (5)-dimethylimidazole, 1-ethylimidazole, 2-ethylimidazole, 1-phenylimidazole, 2-phenylimidazole, 4 (5)-phenylimidazole and N,N-dimethylaminopyridine, guanidine, 1,1,3,3-tetramethylguanidine, pyridine, 1-azanaphthalene (quinoline), N-methylpiperidine, N-methylmorpholine, N,N′-dimethylpiperazine, N,N-dimethylaniline, and mixtures thereof.

7. The process as claimed in claim 1 , wherein the polyoxyalkylene polyol has a proportion of secondary OH end groups of at least 75%, based on the sum total of primary and secondary OH end groups, as determined by means of 1H NMR spectroscopy.

8. The process as claimed in claim 1 , wherein the polyoxyalkylene polyol is a polyether polyol and/or polyethercarbonate polyol.

9. The process as claimed in claim 8 , wherein the polyoxyalkylene polyol is a polyether polyol prepared by reaction of an H-functional starter substance with alkylene oxide in the presence of a double metal cyanide catalyst.

10. The process as claimed in claim 9 , wherein the alkylene oxide is ethylene oxide and/or propylene oxide.

11. The process as claimed in claim 10 , wherein the proportion by weight of propylene oxide is 80% by weight to 100% by weight based on the sum total of the masses of propylene oxide and of ethylene oxide metered in.

12. The process as claimed in claim 1 , wherein the process is performed without addition of a solvent.

13. The process as claimed in claim 1 , wherein the cyclic carbonate is added continuously or stepwise to the polyoxyalkylene polyol and is converted to the polyoxyalkylenecarbonate polyol.

Assignees

• Covestro Deutschland Ag

Inventors

• Vogelsang Elisabeth
• Hofmann Joerg
• Lorenz Klaus
• Sander Philipp
• Werda Stefan
• Schuetze Mike

Classifications

• C08G2261/126

  block · CPC title

• C08G65/3328

  heterocyclic · CPC title

• C08G65/2672

  Nitrogen or compounds thereof · CPC title

• C08G65/2663

  Metal cyanide catalysts, i.e. DMC's · CPC title

• C08G65/2606

  containing hydroxyl groups · CPC title