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Hyaluronan and biodegradable high polymer modified material and preparation method

A technology of polymer material and hyaluronic acid, which is applied in the field of hyaluronic acid and biodegradable polymer modified materials and preparation, can solve the problem that hyaluronic acid cannot achieve the therapeutic effect and the like

Active Publication Date: 2013-02-06
IMEIK TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, non-cross-linked hyaluronic acid cannot achieve the desired therapeutic effect as a dermal filler

Method used

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  • Hyaluronan and biodegradable high polymer modified material and preparation method
  • Hyaluronan and biodegradable high polymer modified material and preparation method
  • Hyaluronan and biodegradable high polymer modified material and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Composite cross-linking of hyaluronic acid and sodium alginate (the first type of polymer)

[0050] 4g of hyaluronic acid and 1g of sodium alginate were dissolved in 20mL of 2% (mass fraction) tetrabutylammonium hydroxide aqueous solution. 4%), stirred and reacted at 25°C for 20~24h, adjusted the pH=7-7.5 with 2mol / L hydrochloric acid after the reaction, washed the gel with 200mL of 75% ethanol aqueous solution and dehydrated the gel, at 50°C , dried under a vacuum of 0.08-0.09MPa for 4-6h; then the gel was swelled in 200mL pH=7 phosphate buffer for 72-96h, and when the swelling equilibrium was reached, it was taken out and soaked in 15% chloride Calcium aqueous solution, take it out after 24-36 hours, you can get hyaluronic acid-sodium alginate gel with higher hardness. It has been tested that the maximum destructive pressure that the gel can withstand is 30N, while the maximum destructive pressure that the cross-linked hyaluronic acid gel with the same cro...

Embodiment 2

[0051] Example 2: Hyaluronic acid grafted polylactic acid (PLA) (hydroxyl grafted)

[0052] Dissolve 2g of hyaluronic acid in 50mL of 2% tetrabutylammonium hydroxide aqueous solution; then dissolve 30g of polylactic acid in 150mL of dichloromethane, and then add 0.6g of cross-linking agent pentaerythritol tetraglycidyl ether to the solution (PETE); mix the aqueous solution and dichloromethane solution under stirring, react at 25°C for 12-14h, after the reaction is completed, use 2mol / L hydrochloric acid to adjust the pH to 7~7.5, and then under the vacuum of 0.09MPa The dichloromethane was distilled off, and the reaction product was washed with 400 mL of ethanol to dehydrate and remove tetrabutylammonium chloride impurities to obtain an amphiphilic graft polymer.

[0053]

Embodiment 3

[0054] Example 3: Hyaluronic acid grafted polylactic acid (PLA) (carboxyl grafted)

[0055] Dissolve 2g of hyaluronic acid in 50mL of tetrabutylammonium chloride aqueous solution with a mass fraction of 2%, adjust the pH to 4.0~5.0 with 1mol / L hydrochloric acid; then dissolve 10g of polylactic acid in 50mL of dichloromethane, add Diamine 0.2g is used as cross-linking agent; after mixing dichloromethane solution and hyaluronic acid aqueous solution, add 0.4g dicyclohexylcarbodiimide (DCC) as carboxyl activator and 0.4g N-hydroxysuccinimide Amine is used as a co-activator, the temperature is raised to 40°C, and the reaction is carried out for 2~3h. After the reaction is completed, the pH is adjusted to 7~7.5 with 1% NaOH solution, and the dichloromethane is sucked dry at 25°C under a vacuum of 0.09MPa. The reaction product was then washed with 400 mL of ethanol to dehydrate and remove impurities to obtain a grafted polymer.

[0056]

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Abstract

The invention relates to a hyaluronan and biodegradable high polymer modified material and a preparation method, in particular to a method for complex crosslinking and grafting of the hyaluronan and a derivative thereof with a biodegradable high polymer with active functional groups through a crosslinking agent. The method comprises the steps of taking the hyaluronan and the biodegradable high polymer as raw materials, conducting complex crosslinking or grafting reaction of a hyaluronan aqueous solution and at least one biodegradable high polymer solution with the presence of the crosslinking agent, and removing a solvent. According to the method, plural gel, an amphiphilic polymer, a graft polymer, a star polymer and a microsphere can be prepared. The method has the advantages that the reaction condition is simple, the utilization ratio of the crosslinking agent is high, the residual quantity of the crosslinking agent is small, and the gel is higher in thermostability and good in biological compatibility. The method is applicable to the fields of cosmetics, tissue filling and repair, biological stents, ophthalmonogy, sustained-release delivery and targeted drug delivery and the like, and has a wider application prospect.

Description

technical field [0001] The invention relates to a hyaluronic acid and biodegradable polymer modified material and a preparation method thereof. Specifically, the hyaluronic acid and its derivatives are compounded and cross-linked with a biodegradable polymer having an active functional group through a cross-linking agent. Methods of linking and grafting. Background technique [0002] Hyaluronic acid (Hyaluronan, HA), also known as hyaluronic acid, is a high molecular non-protein acidic mucopolysaccharide widely present in the human body and other organisms. It has been confirmed by research that hyaluronic acid is a high molecular polymer formed by repeatedly connecting N-acetylglucosamine and glucuronic acid through β-1,4 and β-1,3 glycosidic bonds. The sugars, β-D-glucuronic acid and N-acetylamino-D-glucosamine, are composed in an equimolar ratio. With its unique molecular structure and physical and chemical properties, hyaluronic acid shows a variety of important physio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/24C08L5/08C08L1/02C08L1/26C08L5/04C08L5/02C08L3/02C08L77/04C08L77/00C08L89/00C08L67/04C08L71/08C08L71/00
Inventor 简军李睿智
Owner IMEIK TECH DEV CO LTD
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