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Poly benzyl glutamate-containing degradable composite material and preparation thereof

A technology of poly(benzyl glutamic acid) and composite materials, applied in the field of biomedical composite materials, can solve the problem of not containing functional groups, and achieve the effects of widening applications, shortening technical routes, and low toxicity

Inactive Publication Date: 2008-10-08
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ring-opening polymerization of acid anhydrides generally uses primary amines, alkoxy anions and tertiary amines as initiators to prepare the corresponding polyamino acids. These products do not contain functional groups and cannot provide usable functional groups for the next application.

Method used

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  • Poly benzyl glutamate-containing degradable composite material and preparation thereof
  • Poly benzyl glutamate-containing degradable composite material and preparation thereof
  • Poly benzyl glutamate-containing degradable composite material and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] a. Mix 10 grams of L-glutamic acid, 40 mL of benzyl alcohol and 14.5 mL of hydrobromic acid solution (30% by weight), and heat to 60° C.; after the reaction solution becomes clear, cool down to room temperature, and mix The solution was poured into 500 mL of pyridine and ethanol mixture with a volume ratio of 1:5 to obtain a white precipitate, which was placed overnight at 2°C; filtered, washed with ethanol and ether to obtain a crude product, which was recrystallized with ethanol and dried to obtain White crystalline product, L-glutamic acid-γ-benzyl ester;

[0030] b. Dissolve 5 grams of L-benzyl glutamate in 28 mL of tetrahydrofuran, and when the temperature rises to 40° C., add 4 grams of bis(trichloromethyl) carbonate; stop heating after the reaction mixture becomes clear, and fill with nitrogen 30 minutes; then the reaction solution was concentrated to 20 mL, poured into 100 mL of anhydrous petroleum ether to obtain flocculent crystals, the precipitate was filtere...

Embodiment 2

[0040] (1) Synthesis of γ-benzyl-L-glutamic acid-N-carboxylic acid anhydride

[0041] a. Mix 10 grams of L-glutamic acid, 60 mL of benzyl alcohol and 36 mL of hydrobromic acid solution (the percentage concentration is 45%), heat to 80 ° C; Pour into 500mL of pyridine and ethanol mixture with a volume ratio of 1:8 to obtain a white precipitate, which is placed overnight at 4°C; filter, wash with ethanol and ether respectively to obtain a crude product, recrystallize the crude product with ethanol, and dry to obtain a white crystal The product, namely L-glutamic acid-γ-benzyl ester;

[0042] b. Dissolve 5 grams of L-benzyl glutamate in 75 mL of tetrahydrofuran, and when the temperature rises to 55° C., add 7.5 grams of bis(trichloromethyl)carbonate, stop heating after the reaction mixture becomes clear, and fill with nitrogen 45 minutes; then the reaction solution was concentrated to 20 mL, poured into 120 mL of anhydrous petroleum ether to obtain flocculent crystals, filtered,...

Embodiment 3

[0046] (1) Synthesis of γ-benzyl-L-glutamic acid-N-carboxylic acid anhydride

[0047] a. 10 grams of L-glutamic acid, 50 mL of benzyl alcohol and 29 mL of hydrobromic acid solution (38% by weight) were mixed and heated to 70 ° C; after the reaction solution became clear, it was cooled to room temperature, and the mixed solution was Pour it into 400 mL of pyridine and ethanol mixture with a volume ratio of 1:6 to obtain a white precipitate, which is placed at 3°C ​​overnight; filter, wash with ethanol and ether respectively to obtain a crude product, recrystallize the crude product with ethanol, and dry to obtain a white Crystalline product, namely L-glutamic acid-γ-benzyl ester;

[0048] b. Dissolve 5 g of benzyl L-glutamate in 56 mL of tetrahydrofuran, and when the temperature rises to 50° C., add 6 g of bis(trichloromethyl)carbonate; stop heating after the reaction mixture becomes clear, and fill with nitrogen 60 minutes; then the reaction solution was concentrated to 20 mL...

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Abstract

The invention discloses a biodegradable composite material containing poly benzyl glutamate, and the preparation method. The method comprises three parts, namely, the synthesis of gamma-benzyl-L-glutamate N-carboxyl anhydride, the synthesis of end-allyl-poly benzyl glutamate, and the preparation of composite material. The synthesis of end-allyl-poly benzyl glutamate takes the gamma-benzyl-L-glutamate N-carboxyl anhydride as the monomer and takes diallyl amine as the initiator to prepare the end-allyl-poly benzyl glutamate through reaction in methylene chloride solution; through UV cross linking, polyethylene glycol dimethacrylate or 2-methacryloyloxyethyl phosphorylcholine with good hydrophilicity, biocompatibility and blood compatibility is introduced into the poly benzyl glutamate to prepare the biodegradable composite material containing poly benzyl glutamate. The composite material can be used for tissue repair in clinical medicine and has the advantages of simple preparation process and equipment, which has good application prospect and scientific significance.

Description

technical field [0001] The invention relates to a biomedical composite material containing polyamino acid derivatives, in particular to a polybenzyl glutamate composite material with degradable performance and good biocompatibility and a preparation method thereof. Background technique [0002] Polyamino acids are a class of biodegradable polymers with low toxicity, good biocompatibility, and easy absorption and metabolism by the body. Therefore, they are widely used in medical fields such as controlled drug release and tissue engineering. Compared with other amino acids, polybenzyl glutamate has the characteristics of easy processing, easy functionalization and low immunogenicity, and has become a polyamino acid that has been studied more in recent years. However, due to its poor hydrophilicity and slow degradation rate, its application is limited. Therefore, the study of its new modified biomedical composite materials has great clinical application value. [0003] The pre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F299/02C08F283/04C08F2/50
Inventor 王迎军周秀苗任力汪凌云
Owner SOUTH CHINA UNIV OF TECH
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