IP Library Granted Patent US 9,284,401
Granted Patent B2
US 9,284,401 · App. 11/713,898 · Granted Mar 15, 2016

Process for the preparation of polyether-ester polyols

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Quick Facts
Patent No.
US 9,284,401
App. No.
11/713,898
Granted
Mar 15, 2016
Kind
B2
Abstract

The present invention provides a process for the preparation of polyols based on fatty acid esters and starter compounds having Zerewitinoff-active hydrogen atoms and the use thereof for the preparation of polyurethane materials.

Claims (17)

1. A one pot, one step process for the preparation of a polyether-ester polyol comprising reacting one or more starter compounds having Zerewitinoff-active hydrogen atoms with one or more alkylene oxides in the presence of an amine catalyst that is employed in an amount of 200 ppm to 10,000 ppm, based on the amount of end product of the process and in the presence of one or more fatty acid esters having fatty acid radicals that contain no free OH groups to produce a polyether-ester polyol, with the proviso that the process does not use a salt of an alkali metal or alkaline earth metal as a catalyst to produce the polyether-ester polyol.

2. The process according to claim 1 , wherein the fatty acid ester comprises about 5 to about 85 wt. %, based on the amount of end product of the process.

3. The process according to claim 1 , wherein the fatty acid ester is produced from one of auric acid, myristic acid, palmitic acid, stearic acid, palmitoleic acid, oleic acid, erucic acid, linoleic acid, Underlie acid, elaeostearic acid, arachidonic acid and mixtures thereof.

4. The process according to claim 1 , wherein the starter compound is selected from propylene glycol, ethylene glycol, diethylene glycol, dipropylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butane diol, hexanediol, pentanediol, 3-methyl-1,5-pentanediol, 1,12-dodecanediol, glycerol, trimethylolpropane, trimethylolethane, triethanolamine, pentaerythritol, sorbitol, sucrose, α-methyl glucoside, fructose, hydroquinone, pyrocatechol, resorcinol, bisphenol F, bisphenol A, 1,3,5-trihydroxybenzene, condensates of formaldehyde and phenol or melamine or urea containing methylol groups, Mannich bases, ammonia, ethanolamine, diethanolamine, isopropanolamine, diisopropanolamine, ethylenediamine, hexamethylenediamine, aniline, isomers of toluidine, isomers of diaminotoluene, and isomers of diaminodiphenylmethane.

5. The process of claim 1 , wherein the amine catalyst is an aliphatic amine or alkanolamine comprising N,N-dimethylbenzylamine, dimethylaminoethanol, dimethylaminopropanol, N-methyldiethanolamine, trimethylamine, N,N-dimethylcyclohexylamine, N-methylpyrrolidine, N,N,N′,N′-tetramethylethylenediamine, diazabicyclo[2,2,2]octane, 1,4,dimethylpiperazine or N-methylmorpholine.

6. The process of claim 1 , wherein the amine catalyst comprises an aromatic amine comprising imidazole, an alkyl-substituted imidazole, N,N-dimethylaniline, 4-(N,N-dimethyl)aminopyridine, a copolymer of (i) 4-vinylpyridine or vinylimidazole, and (ii) divinylbenzene.

7. A polyether-ester polyol produced by a one pot, one step process comprising reacting one or more starter compounds having Zerewitinoff-active hydrogen atoms with one or more alkylene oxides in the presence of an amine catalyst that is employed in an amount of 200 ppm to 10,000 ppm, based on the amount of end product of the process and in the presence of one or more fatty acid esters having fatty acid radicals that contain no free OH groups, with the proviso that the process does not use a salt of an alkali metal or alkaline earth metal as a catalyst to produce the polyether-ester polyol.

8. The polyether-ester polyol of claim 7 , wherein the amine catalyst is an aliphatic amine or alkanolamine comprising N,N-dimethylbenzylamine, dimethylaminoethanol, dimethylaminopropanol, N-methyldiethanolamine, trimethylamine, N,N-dimethylcyclohexylamine, N-methylpyrrolidine, N,N,N′,N′-tetramethylethylenediamine, diazabicyclo[2,2,2]octane, 1,4,dimethylpiperazine or N-methylmorpholine.

9. The polyether-ester polyol of claim 7 , wherein the amine catalyst comprises an aromatic amine comprising imidazole, an alkyl-substituted imidazole, N,N-dimethylaniline, 4-(N,N-dimethyl)aminopyridine, a copolymer of (i) 4-vinylpyridine or vinylimidazole, and (ii) divinylbenzene.

10. A process for the preparation of a polyurethane foam or elastomer comprising reacting a polyisocyanate with the polyether-ester polyol according to claim 7 .

11. A process for the preparation of a polyurethane foam or elastomer comprising reacting a polyisocyanate with a polyether-ester polyol produced by a one pot, one step process comprising reacting one or more starter compounds having Zerewitinoff-active hydrogen atoms with one or more alkylene oxides in the presence of an amine catalyst and in the presence of one or more fatty acid esters having fatty acid radicals that contain no free OH groups, with the proviso that the polyether-ester polyol is produced by a process that does not use a salt of an alkali metal or alkaline earth metal as a catalyst to produce the polyether-ester polyol.

12. The process according to claim 11 , wherein the polyisocyanate is selected from ethylene-diisocyanate, 1,4-tetramethylene-diisocyanate, 1,6-hexamethylene-diisocyanate (HDI), 1,12-dodecane-diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- and -1,4-diisocyanate and mixtures thereof, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane, 2,4- and 2,6-hexahydrotoluylene-diisocyanate and mixtures thereof, hexahydro-1,3- and -1,4-phenylene-diisocyanate, perhydro-2,4′- and -4,4′-diphenylmethane-diisocyanate, 1,3- and 1,4-phenylene-diisocyanate, 1,4-durol-diisocyanate (DDI), 4,4′-stilbene-diisocyanate, 3,3′-dimethyl-4,4′-biphenylene-diisocyanate (DIBDI), 2,4- and 2,6-toluylene-diisocyanate (TD) and mixtures thereof, diphenylmethane-2,4′-diisocyanate and/or diphenylmethane-4,4′-diisocyanate (MDI) and naphthylene-1,5-diisocyanate (NDI).

13. The process according to claim 11 , wherein the fatty acid ester is produced from one of lauric acid, myristic acid, palmitic acid, stearic acid, palmitoleic acid, oleic acid, erucic acid, linoleic acid, linolenic acid, elaeostearic acid, arachidonic acid and mixtures thereof.

14. The process according to claim 11 , wherein the starter compound is selected from propylene glycol, ethylene glycol, diethylene glycol, dipropylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, hexanediol, pentanediol, 3-methyl-1,5-pentanediol, 1,12-dodecanediol, glycerol, trimethylolpropane, trimethylolethane, triethanolamine, pentaerythritol; sorbitol, sucrose, α-methyl glucoside, fructose, hydroquinone, pyrocatechol, resorcinol, bisphenol F, bisphenol A, 1,3,5-trihydroxybenzene, condensates of formaldehyde and phenol or melamine or urea containing methylol groups, Mannich bases, ammonia, ethanolamine, diethanolamine, isopropanolamine, diisopropanolamine, ethylenediamine, hexamethylenediamine, aniline, isomers of toluidine, isomers of diaminotoluene, and isomers of diaminodiphenylmethane.

15. The process of claim 11 , wherein the amine catalyst is an aliphatic amine or alkanolamine comprising N,N-dimethylbenzylamine, dimethylaminoethanol, dimethylaminopropanol, N-methyldiethanolamine, trimethylamine, N,N-dimethylcyclohexylamine, N-methylpyrrolidine, N,N,N′,N′-tetramethylethylenediamine, diazabicyclo[2,2,2]octane, 1,4,dimethylpiperazine or N-methylmorpholine.

16. The process of claim 11 , wherein the amine catalyst comprises an aromatic amine comprising imidazole, an alkyl-substituted imidazole derivative, N,N-dimethylaniline, 4-(N,N-dimethyl)aminopyridine, a copolymer of (i) 4-vinylpyridine or vinylimidazole, and (ii) divinylbenzene.

17. The polyurethane foam or elastomer made by the process according to claim 11 .

Assignments (4)
CHANGE OF NAME Recorded Apr 5, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038358/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2008
From: BAYER ANTWERPEN COMM. V.
To: BAYER MATERIALSCIENCE LLC; BAYER MATERIALSCIENCE AG
Reel/Frame 020493/0514 →
THIS IS A CORRECTIVE ASSIGNMENT TO CORRECT THE THIRD ASSIGNEE WAS OMITTED ON REEL 019054 FRAME 0019 Recorded Apr 9, 2007
From: LORENZ, KLAUS; ALBERS, REINHARD; OTTO, FRANK; LEYER, ULRICH; WARDIUS, DON S.; HEADLEY, KEITH J.
To: BAYER MATERIALSCIENCE LLC; BAYER MATERIALSCIENCE AKTIENGESELLSCHAFT; BAYER ANTWERPEN COMM. V.
Reel/Frame 019167/0797 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2007
From: LORENZ, KLAUS; ALBERS, REINHARD; OTTO, FRANK; LEYRER, ULRICH; WARDIUS, DON S.; HEADLEY, KEITH J.
To: BAYER MATERIALSCIENCE LLC; BAYER MATERIALSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 019054/0019 →