Method for preparing glycosyl amide modified polysiloxane

An aminopolysiloxane and polysiloxane technology, which is applied to non-active ingredients in medical preparations, pharmaceutical formulations, etc., can solve the problems of high toxicity of allylamine, expensive catalyst chloroplatinic acid, and lengthy reaction process. and other problems, to achieve the effect of being conducive to industrialization, cheap catalysts, and reducing the reaction process

Active Publication Date: 2011-01-12
CHINA RES INST OF DAILY CHEM IND
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  • Summary
  • Abstract
  • Description
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Problems solved by technology

[0003] The sugar-based amide-modified polysiloxanes synthesized by these methods all have hydrosilylation reactions in the synthesis process, and the catalyst chloroplatinic...

Method used

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  • Method for preparing glycosyl amide modified polysiloxane

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Embodiment 1

[0020] Add 5.93kg of octamethylcyclotetrasiloxane, 6.18kg of aminoethylaminopropyldimethoxymethylsilane, 1.62kg of hexamethyldisiloxane, and 10.9g of tetramethylammonium hydroxide into the reaction kettle , heated to dissolve, the temperature was controlled at 30°C, and after 5 hours of reaction, the temperature was raised to 135°C to deactivate the catalyst. Aminoethylaminopropyl polysiloxane was obtained after vacuum distillation, and the primary ammonia value was measured by potentiometric titration. Add equimolar gluconolactone according to the number of moles of the primary ammonia value, use methanol as a solvent, and react at a temperature of 70° C. for 6 hours. The solvent methanol was evaporated, and the product glucamide-modified aminoethylaminopropyl polysiloxane was obtained after vacuum drying. The minimum surface tension of its aqueous solution measured with a K12 surface tensiometer is 23mN / m, and the critical micelle concentration is 35mg / L.

Embodiment 2

[0022] Add 2.97kg of octamethylcyclotetrasiloxane, 5.74kg of aminopropyldiethoxymethylsilane, 1.62kg of hexamethyldisiloxane, and 112g of potassium hydroxide in the reaction kettle, heat and dissolve, and control the temperature at After reacting at 220°C for 7 hours, add acetic acid to neutralize the catalyst, deactivate it and filter it out. Aminopropyl polysiloxane was obtained after rectification under reduced pressure, and the ammonia value was measured by potentiometric titration. According to the number of moles of the ammonia value, three times the moles of gluconolactone were added, and ethanol was used as a solvent, and the reaction was carried out at a temperature of 30° C. for 5 hours. The solvent ethanol was evaporated, and the product glucamide-modified aminopropyl polysiloxane was obtained after vacuum drying. The lowest surface tension of its aqueous solution measured with a K12 surface tensiometer is 24mN / m, and the critical micelle concentration is 23mg / L. ...

Embodiment 3

[0024] Add 1.12kg of hexamethylcyclotrisiloxane, 2.45kg of aminopropyldimethoxymethylsilane, 0.81kg of hexamethyldisiloxane, and 104.5g of tetrabutylphosphonium hydroxide in the reaction kettle, and heat to dissolve. The temperature is controlled at 80°C, and after 8 hours of reaction, the temperature is raised to 110°C to deactivate the catalyst. Aminopropyl polysiloxane was obtained by rectification under reduced pressure, and the ammonia value was measured by potentiometric titration. According to the number of moles of ammonia value, add twice moles of lactobionic acid, use isopropanol as a solvent, and react at a temperature of 90° C. for 10 hours. The solvent isopropanol was distilled off, and the product lactosamide-modified aminopropyl polysiloxane was obtained after vacuum drying. The minimum surface tension of its aqueous solution measured with a K12 surface tensiometer is 26mN / m, and the critical micelle concentration is 74mg / L.

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Abstract

The invention discloses a method for preparing glycosyl amide modified polysiloxane. The method comprises the following steps of: reacting cyclosiloxane, hexamethyldisiloxane and aminosilane serving as raw materials under the action of a catalyst at the temperature of between 30 and 220 DEG C for 4 to 8 hours, wherein the molar ratio of the cyclosiloxane to the aminosilane to the hexamethyldisiloxane is 0.25-2.25:3-5:1; the molar ratio of the catalyst to the sum of the cyclosiloxane, the aminosilane and the hexamethyldisiloxane is 0.1 to 1; inactivating the catalyst after the reaction is finished; performing reduced pressure distillation to obtain the amino-polysiloxane; reacting the amino-polysiloxane and glycosyl lactone or saccharic acid in low-carbon alcohol serving as a solvent at the temperature of between 30 and 200 DEG C for 5 to 10 hours, wherein the molar ratio of primary amine of the amino-polysiloxane to the glycosyl lactone or saccharic acid is 1-5:1; and evaporating off the solvent to obtain the glycosyl amide modified polysiloxane after the reaction is finished. The method has the advantages of low cost, no toxicity and large-scale industrialization.

Description

technical field [0001] The invention relates to a preparation method of glycosylamide modified polysiloxane. Background technique [0002] Existing methods for preparing glycosylamide-modified polysiloxanes, such as Feng Shengyu (Carbohydrate Polymer, 2006, 65, 321) reported a method for preparing glycosylamide-modified polysiloxanes. After reacting the ester with allylamine, the hydroxyl group is protected, and then the hydrosilylation reaction is carried out with the hydrogen-containing polysiloxane, and then deprotected to obtain the glycosylamide-modified polysiloxane. German patent DE 4,318,539 reports a method for preparing glycosylamide-modified polysiloxane, and the product is obtained by reacting aminosiloxane with sugar lactone. But aminosiloxanes are obtained by hydrosilylation of allylamines. Wagner R. (Applied Organometallic Chemistry, 1996, 10, 421) reported a method for preparing glycosylamide-modified polysiloxane, and obtained epoxy-modified polysiloxane b...

Claims

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Application Information

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IPC IPC(8): C08G77/38C08G77/26A61K47/34
Inventor 杜志平王亮王国永王万绪台秀梅
Owner CHINA RES INST OF DAILY CHEM IND
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