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Aliphatic polyester-polyamino acid Y-type three-arm block copolymers and synthetic method thereof

An aliphatic polyester and block copolymer technology, applied in the field of polymer biomedical materials, can solve the problems of difficult and limited synthesis methods, and achieve the effects of low cost, excellent mechanical and processing properties, and wide application prospects.

Inactive Publication Date: 2008-07-09
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the above-mentioned copolymers of aliphatic polyesters and polyamino acids, whether binary copolymers or terpolymers, are limited to linear structures.
Due to the difficulty in the synthesis method, there has been no report on the synthesis of aliphatic polyesters and polyamino acid heteromulti-arm block copolymers, although multi-arm polymers, star polymers, comb polymers and dendritic polymers are known It is of great significance and value in theoretical research and industrial application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of polylactide-polybenzyl glutamate Y-type three-arm block copolymer.

[0018] 1) Dissolve 10g of 2-amino-1,3-propanediol in 265ml of 10% aqueous sodium bicarbonate solution, then add 150ml of dioxane, cool to below 0°C, add 15ml of benzyl chloroformate dropwise, and react at 0°C After 3 hours, the reaction was continued at room temperature for 12 hours. After the product was diluted with a large amount of water, it was extracted with ethyl acetate. The obtained crude product was recrystallized with ethyl acetate to obtain white needle-like crystals, which were dried in vacuo to obtain benzyloxycarbonyl-protected 2-amino-1,3-propanediol with a yield of about 90%.

[0019]2) Add 0.001mol Benzyloxycarbonyl-protected 2-amino 1,3-propanediol and 0.03, 0.04, 0.06mol aliphatic cyclic ester monomer lactide into the reaction flask respectively, after azeotropic water removal with toluene, Under the condition of water without oxygen, add toluene solvent e...

Embodiment 2

[0028] Example 2: Preparation of polycaprolactone-polybenzyl glutamate Y-type block copolymer.

[0029] Add 0.001 mol of 2-amino-1,3-propanediol protected by benzyloxycarbonyl group and 0.03, 0.04, 0.06 mol ε-caprolactone respectively into the reaction flask, and the other steps are the same as in Example 1. See Table 3 and Table 1 for various polymerization results. Four.

[0030] Table three:

[0031] Numbering

[0032] In the above table, A / I refers to the mol ratio of monomer ε-caprolactone and initiator; Productive rate is the ratio of polymer weight and caprolactone monomer and initiator total weight; DP (PCL) by 1 Obtained by H NMR; M n a is the number average molecular weight of polycaprolactone, given by 1 Obtained by H NMR; M n b is the number average molecular weight of polycaprolactone, obtained by GPC.

[0033] Table four:

[0034] Numbering

[0035] M in the above table n (I) refers to the number-average molecular weight of PCL; A / I...

Embodiment 3

[0036] Example 3: Preparation of polyglycolide-polybenzyl glutamate Y-type block copolymer.

[0037] Add 0.001 mol of 2-amino-1,3-propanediol protected by benzyloxycarbonyl and 0.03 mol of glycolide into the reaction flask, after benzene azeotropic water removal, under anhydrous and oxygen-free conditions, add lactide mono The toluene solvent of body equal weight, and the stannous octoate catalyst of 1% of lactide monomer weight, at 100 ℃, stirring reaction 12 hours, other steps are the same as embodiment 1, obtain Y-type block copolymer polyglycolic acid Ester-polybenzyl glutamate, yield: 92.2%, by 1 The DP (PGA) of the polyester two arms measured by H NMR=27 (the number average molecular weight is 3130), the polyamino acid arm DP (PBLG)=8 (the number average molecular weight is 1750), and the total average molecular weight of the three arms is 4880.

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PUM

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Abstract

The invention relates to a Y-shaped three-arm segmented copolymer of aliphatic polyester namely polyamino acid and a process for synthesis, which belongs to the high-polymer biological medicine material field. And the process for synthesis comprises protecting amidogens of 2-amidocyanogen-1 and 3-propylene glycol with benzyl chloroformate, ringopening and polymerizing 2-amidocyanogen-1 and 3-propylene glycol with aliphatic cyclic esters monomer in benzene or toluene dissolvent under the condition of warming up and stirring and without water and oxygen through utilizing stannous octoate as catalyst, utilizing amidogens to be macromolecule initiating agent after de-protecting, triggering alpha- amino acid-N-carboxylic acid anhydrides to ring-open and polymerize, getting Y-shaped segmented copolymer of carboxy group which is protected by benzyl group, forming relative polymer with free carboxy group through dewatering hydrogen bromide or catalyzing hydrogenating and deacidizing palladium-charcoal, and then getting the Y-shaped segmented copolymer which can be biodegraded and can have biology functionalization. The invention can be widely applied in the filed such as internal fixation of bone fracture, medicinal carrier, tissue engineering scaffold and the like.

Description

technical field [0001] The invention relates to a synthesis method of a biofunctional aliphatic polyester-polyamino acid block copolymer, belonging to the field of polymer biomedical materials. technical background [0002] Biodegradable polymer materials have good biocompatibility, can collapse, degrade and metabolize by themselves under physiological conditions, and then be absorbed or excreted by organisms without toxic side effects to the human body, so they can be used as tissue engineering scaffold materials or Drug release carrier material. As tissue engineering scaffold materials, they are conducive to the adsorption and growth of growth factors and cells on the surface, and gradually degrade and be absorbed with the proliferation of cells, the growth of tissues and the gradual formation of organs, so as to repair defects or functional failure Organs, without the need for secondary surgery to remove the scaffold material. As a drug carrier, in addition to the diffu...

Claims

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Application Information

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IPC IPC(8): C08G69/44
Inventor 景遐斌孙静陈学思石全谢志刚黄宇彬
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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