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Particle emulsifier based on colloid self-assembled by hydrophobic modified hyaluronic acid and preparation method of particle emulsifier

A granular emulsifier and hyaluronic acid technology, applied in skin care preparations, cosmetics, etc., can solve problems such as vacancies, and achieve good emulsification effect, good stability, and high added value

Inactive Publication Date: 2015-12-30
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still gaps in the application of hyaluronic acid-based assembled colloids in emulsifiers.

Method used

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  • Particle emulsifier based on colloid self-assembled by hydrophobic modified hyaluronic acid and preparation method of particle emulsifier
  • Particle emulsifier based on colloid self-assembled by hydrophobic modified hyaluronic acid and preparation method of particle emulsifier
  • Particle emulsifier based on colloid self-assembled by hydrophobic modified hyaluronic acid and preparation method of particle emulsifier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Preparation of Hyaluronic Acid and Tetrabutylammonium Hydroxide Complex (HA-TBA)

[0029] 1.0g sodium hyaluronate (molecular weight is 11kDa) is dissolved in deionized water to prepare a 1wt% solution, stirred at room temperature until completely dissolved, and 3.0g strongly acidic cation exchange resin (H type, IR-120 ), after stirring for 5 hours, filter to remove the strongly acidic cation exchange resin; use 25% tetrabutylammonium hydroxide to adjust the pH of the filtrate to 7.0-7.03; freeze-dry to obtain the complex of hyaluronic acid and tetrabutylammonium hydroxide.

[0030] (2) Preparation of 7-(2-hydroxyethoxy)-4-methylcoumarin (HEMC)

[0031] Dissolve 5.0g of 7-hydroxy-4-methylcoumarin, 5.0g of 2-bromoethanol, and 3.0g of potassium carbonate in 50mL of ethanol, and reflux at 85°C for 24 hours; after the reaction, dissolve potassium carbonate in water and extract with ether; The organic layer was dried with anhydrous magnesium sulfate, and the solid was r...

Embodiment 2

[0042] (1) Preparation of hyaluronic acid and tetrabutylammonium hydroxide compound (HA-TBA), the method is the same as step (1) in Example 1.

[0043] (2) Preparation of 7-(2-hydroxyethoxy)-4-methylcoumarin (HEMC), the method is the same as step (2) in Example 1.

[0044] (3) Synthesis of HEMC modified hyaluronic acid

[0045]Weigh 0.5g of HA-TBA and dissolve it in 10mL of anhydrous DMSO. After complete dissolution, add 0.9898g of DCC and 0.2281g of DMAP, and stir at 60°C for 3h to activate the carboxyl group. Then 1.0736g HEMC was weighed and added into the reaction solution, and reacted at 60°C for 48h.

[0046] The reaction solution was suction filtered to remove insoluble matter, the filtrate was precipitated with acetone, and the centrifugation was repeated twice; the solid obtained by centrifugation was dissolved in 10-15mL DMSO, and the solution was dialyzed with sodium chloride solution (MWCO=3500Da) for one day, and then dialyzed with deionized water Three to four ...

Embodiment 3

[0049] (1) Preparation of hyaluronic acid and tetrabutylammonium hydroxide compound (HA-TBA), the method is the same as step (1) in Example 1.

[0050] (2) Preparation of 7-(2-hydroxyethoxy)-4-methylcoumarin (HEMC), the method is the same as step (2) in Example 1.

[0051] (3) Synthesis of HEMC modified hyaluronic acid

[0052] Weigh 0.5g HA-TBA and dissolve it in 10mL anhydrous DMSO, add 0.6599gDCC and 0.2144gDMAP after complete dissolution, stir at 60°C for 3h to activate the carboxyl group; then weigh 0.6599gHEMC and add it to the reaction solution, react at 60°C 48h.

[0053] Processing method is the same as step (3) in embodiment one.

[0054] (4) The preparation of HA-HEMC colloidal particles is the same as step (4) in Example 1.

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Abstract

The invention discloses a particle emulsifier based on a colloid self-assembled by hydrophobic modified hyaluronic acid and a preparation method of the particle emulsifier, and belongs to the technical field of self-assembly of natural macromolecules and preparation of the particle emulsifier. The preparation method of the particle emulsifier comprises the following steps: step 1, HA (hyaluronic acid) and TBA-OH (tetrabutylammonium hydroxide) are compounded; step 2, 2-bromoethanol and 7-hydroxyl-4-methylcoumarin are adopted for a nucleophilic substitution reaction, and HEMC (7-(2-hydroxyethoxy)-4-methylcoumarin) is prepared; step 3, a compound obtained in the step 1 and HEMC have an esterification reaction under the action of a catalyst, and HA-HEMC (hydrophobic modified HA) is obtained; step 4, HA-HEMC is self-assembled in a selective solvent, a colloid dispersing agent is formed and freeze-dried, and the particle emulsifier is obtained. The particle emulsifier based on the colloid self-assembled by hydrophobic modified hyaluronic acid has good biocompatibility, can effectively stabilize an oil-water interface and can be applied to the fields of cosmetics, food, bio-medicine and the like.

Description

Technical field: [0001] The invention relates to a particle emulsifier based on hydrophobically modified hyaluronic acid self-assembled colloid and a preparation method thereof, belonging to the technical field of preparation of natural macromolecular self-assembly and particle emulsifiers. Background technique: [0002] Natural macromolecular hyaluronic acid, also known as "hyaluronic acid", is an acidic mucopolysaccharide composed of two disaccharide units D-glucuronic acid and N-acetylglucosamine, which are widely distributed in the extracellular matrix of soft connective tissue in the skin, lungs and intestines. Due to its viscoelasticity, biocompatibility, lubricity, degradability and special water retention, hyaluronic acid is widely used in the fields of biomedicine, food and advanced cosmetics. [0003] There are many studies on hyaluronic acid at home and abroad, but its application is limited due to its strong hydrophilicity and easy degradation. Therefore, it is...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K8/73A61Q19/00A61Q17/04
Inventor 刘晓亚诸超魏玮朱叶顾瑶胡琼卢荣杰
Owner JIANGNAN UNIV
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