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Modification of alkyl polyalkylene glycol with epoxides

A technology of polyalkylene glycol and epoxide, applied in the field of polyalkylene glycol, can solve the problems of difficulty in decomposition, quality reduction and the like

Active Publication Date: 2017-10-17
BASF AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polyalkylene glycols (PAGs) can only be obtained in still acceptable quality at a molar mass of 1100 g / mol due to inherent difficulties in decomposition and / or entrainment of solvents
In the case of prenol as starter, the mass decreases steadily with increasing degree of ethoxylation

Method used

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  • Modification of alkyl polyalkylene glycol with epoxides
  • Modification of alkyl polyalkylene glycol with epoxides
  • Modification of alkyl polyalkylene glycol with epoxides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0194] Example 1 : Reaction of methyldiethylene glycol (methoxyethoxyethanol) and 1,2-epoxy-4-vinylcyclohexane

[0195] Feed material :

[0196] 20.0g methyl diethylene glycol (167mmol; M=120.1g / mol) BASF SE

[0197] 1ml potassium methoxide (32(weight)% methanol solution, 4.2mmol, M=70.1g / mol) BASF SE

[0198] 21.7g 1,2-epoxy-4-vinylcyclohexane (167mmol+5% excess; M=124.12g / mol) SigmaAldrich

[0199] Place 20 g of methyl diethylene glycol in a 100 ml three-necked flask filled with nitrogen after baking, the three-necked flask is equipped with a magnetic stirrer, a diaphragm and a distillation bridge. 1 ml of methanol solution of KOMe was added thereto through the septum through a cannula. In the course of 60 minutes, the methanol was removed by a rotary vane vacuum pump at 23°C and 20 mbar. Then, 5.5 g of 1,2-epoxy-4-vinylcyclohexane was added through a cannula. The resulting mixture was heated to 100°C. During this period, the color of the mixture changed to orange, and a slight...

Embodiment 2

[0206] Feed material :

[0207] 60g methylene polyethylene glycol (available as A 3010E, 20mmol; M=about 3000g / mol obtained), BASF SE

[0208] 2ml potassium methoxide (32(weight)% methanol solution, 8.4mmol, M=70.1g / mol), BASF SE

[0209] 3.91g 1,2-epoxy-4-vinylcyclohexane (30mmol + 5% excess; M = 124.12g / mol), SigmaAldrich

[0210] 60g A 3010E is put into a 100ml three-necked flask filled with nitrogen after baking. The three-necked flask is equipped with a magnetic stirrer, diaphragm, and distillation bridge. 2 ml of KOMe in methanol was added thereto through a cannula. In a period of 40 minutes, the methanol was removed by a rotary vane vacuum pump at 60°C and 20 mbar. The mixture was then heated to 75°C until no more bubbles formed. The mixture was then heated to 100°C and 2.61 g of 1,2-epoxy-4-vinylcyclohexane was added within 25 minutes using a cannula. It was further stirred at 100°C for 2.5 hours. By thin layer chromatography (silica gel, CHCl 3 / Methanol / water 88:11:1...

Embodiment 3

[0214] Feed material :

[0215] 15.0g methyl diethylene glycol (124.9mmol; M=120.1g / mol), BASF SE

[0216] 1ml potassium methoxide (32(weight)% methanol solution, 4.2mmol, M=70.1g / mol), BASF SE

[0217] 19.0g(+)-limonene oxide (124.8mmol; M=152.2g / mol), Sigma Aldrich

[0218] 15 g of methyl diethylene glycol was placed in a 100 ml three-necked flask filled with nitrogen, which was equipped with a magnetic stirrer, a diaphragm and a distillation bridge. 1 ml of methanol solution of KOMe was added thereto through the septum through a cannula. In a period of 30 minutes, the methanol was removed by a rotary vane vacuum pump at 23°C and 20 mbar. Then, 19 g of (+)-limonene oxide was added through a cannula. The resulting mixture was heated to 80°C and stirred at this temperature for 2 hours. During this period, the mixture turned yellow. The mixture was then stirred at a temperature of 140°C for 9.5 hours. By thin layer chromatography (silica gel, CHCl 3 / Methanol / water 88:11:1, KMnO...

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Abstract

The invention relates to a method for producing monoethylenically unsaturated closed alkyl polyalkylene glycols, said polyalkylene glycols obtained according to said method and to the use thereof.

Description

Background of the invention [0001] The present invention relates to a method for preparing a monoethylenically unsaturated alkyl polyalkylene glycol terminated at one end, and relates to a polyalkylene glycol obtainable by the method and its use. [0002] current technology [0003] CN 101712755 describes alkoxy-polyether polymers having at least one double bond at one end of the molecule. The general formula of polymer is AO-(CH 2 CHR 1 O) m -CH 2 -CH 2 OH-CH 2 -OX-CHR 2 =CH 2 , Where A is a straight or branched chain alkyl group, R 1 For H, CH 3 Or CH 2 CH 3 , R 2 Is H or CH 3 And X are various compound groups such as CH 2 -, -Ph-, -CO-, etc. The compound is prepared by the reaction of alcoholate and ethylene oxide. The obtained intermediate is converted by reaction with an epoxy compound containing a terminal double bond, thereby obtaining a polymer. [0004] DE 4004883 (US 5,162,590) describes vinyl polyether alcohols. These act as intermediates and further react with sulfite ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/14C08G65/28C08G65/332C04B24/26C04B24/32
CPCC04B24/2647C04B24/267C04B24/32C04B2103/30C08G65/14C08G65/2609C08G65/3324C08G2650/08
Inventor M·恩斯特
Owner BASF AG