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Process for synthesizing lactic acid-serine copolymer by catalyzing and carrying out ring-opening copolymerization on acetate bicyclo guanidine

A serine copolymer, bicyclic guanidine catalyzed lactide technology, applied in non-active ingredients of medical preparations, pharmaceutical formulations, pharmaceutical science and other directions, can solve the problems of poor catalytic effect, potential safety hazards, etc., to achieve a high degree of biological safety , the effect of reducing production costs and reducing usage

Active Publication Date: 2012-05-09
NANKAI UNIV
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to solve the common use of lactone ring-opening catalysts in the synthesis of polylactide-serine lactate morpholine diketone by the current ring-opening copolymerization method--stannous octoate Sn(Oct) 2 In order to solve the problems of potential safety hazards and poor catalytic effect, a kind of high-efficiency, non-toxic, metal-free, biomimetic organic guanidine salt - bicyclic guanidine acetate is used as catalyst, and lactide and serine morpholine dione are used as comonomers. Process method for synthesizing biomedical degradable material lactic acid-serine copolymer (serine molar content 1-5%) with high biological safety by ring-opening copolymerization

Method used

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  • Process for synthesizing lactic acid-serine copolymer by catalyzing and carrying out ring-opening copolymerization on acetate bicyclo guanidine
  • Process for synthesizing lactic acid-serine copolymer by catalyzing and carrying out ring-opening copolymerization on acetate bicyclo guanidine
  • Process for synthesizing lactic acid-serine copolymer by catalyzing and carrying out ring-opening copolymerization on acetate bicyclo guanidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1——bicyclic guanidine acetate catalyzes L-lactide and (3S, 6S)-serine lactate morpholine diketone ring-opening copolymerization (the reaction conditions of this example and the following examples are to bicyclic guanidine acetate catalysis D, L- Ring-opening copolymerization of lactide and (3S)-serine lactate morpholine dione is also applicable, the same below)

[0033] Add monomer L-lactide 1.000g (6.900mmol) and (3S, 6S)-serine lactate morpholine dione 0.0352g (0.142mmol) in the reaction kettle, control L-lactide and (3S, 6S) -serine morpholine diketone mol ratio is: 98 / 2; Add catalyst bicyclic guanidine acetate 0.0141g (0.071mmol), control the molar weight sum of comonomer lactide and serine morpholine diketone to be the same as that of catalyst bicyclic guanidine acetate The molar ratio is: 100 / 1. After three times of vacuum-filling with argon, the mixture was heated to 130° C. for 3 minutes under vacuum. Then the reaction kettle was moved to 100° C., a...

Embodiment 2

[0036] Example 2—Bicyclic guanidine acetate catalyzed ring-opening copolymerization of L-lactide and (3S, 6S)-serine lactate morpholine dione

[0037] Add monomer L-lactide 1.000g (6.900mmol) and (3S, 6S)-serine lactate morpholine dione 0.1103g (0.443mmol) in the reaction kettle, control L-lactide and (3S, 6S) -serine morpholine diketone mol ratio is: 94 / 6; Add catalyst bicycloguanidine acetate 0.0147g (0.074mmol), control the molar weight sum of comonomer lactide and serine morpholine diketone to be the same as that of catalyst bicycloguanidine acetate The molar ratio is: 100 / 1. After three times of vacuum-filling with argon, the mixture was heated to 140° C. for 5 minutes under vacuum. Then the reaction kettle was moved to 130° C., and the reaction was continued for 20 minutes.

[0038] 20ml of dichloromethane was used to dissolve the polymer in a pressure test tube. Then 5 ml of triethylsilane, 0.1 ml of triethylamine and 0.15 g of palladium dichloride were added. React...

Embodiment 3

[0040] Example 3—Bicyclic guanidine acetate catalyzed ring-opening copolymerization of L-lactide and (3S, 6S)-serine lactate morpholine dione

[0041] Add monomer L-lactide 1.000g (6.900mmol) and (3S, 6S)-serine lactate morpholine dione 0.1921g (0.772mmol) in the reaction kettle, control L-lactide and (3S, 6S) -serine morpholine diketone mol ratio is: 90 / 10; Add catalyst bicyclic guanidine acetate 0.0154g (0.077mmol), control the molar weight sum of comonomer lactide and serine morpholine diketone to be the same as that of catalyst bicyclic guanidine acetate The molar ratio is: 100 / 1. After three vacuum-argon operations, the mixture was heated to 150° C. for 4 minutes under vacuum. Then the reaction kettle was moved to 120° C., and the reaction was continued for 30 minutes.

[0042] 20ml of dichloromethane was used to dissolve the polymer in a pressure test tube. Then 5 ml of triethylsilane, 0.1 ml of triethylamine and 0.15 g of palladium dichloride were added. Reaction at...

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Abstract

The invention relates to a process for synthesizing a lactic acid-serine copolymer (mol content of serine is 1-5%) by catalyzing and carrying out ring-opening copolymerization on acetate bicyclo guanidine. According to the invention, acetate bicyclo guanidine is taken as a catalyst, lactide and serine morpholine diketone are taken as monomer, the bulk is subjected to ring-opening polymerization reaction and O-benzyl removal reaction and synthesized to obtain the lactic acid-serine copolymer. The invention is characterized in that the catalyst acetate bicyclo guanidine is bionic organic guanidine salt with the characteristics of high efficient, nontoxic and metal free. The conversion rate of the copolymerization monomer is high (greater than or equal to 95%), and the yield is high (greaterthan or equal to 93%); the product contains no metal and other toxic residue, and has great biological safety; the number-average molecular weight can be adjusted in the scope of 1.5-3.0*104 and the molecular weight distribution is narrow (PDI is less than or equal to 1.30); the mol content of serine in the copolymer can be adjusted in the scope of 1-5%. The synthesized lactic acid-serine copolymer is amphiphilic functionalized biodegradation polymer, suitable for targeted and controlled release medicine carrier, and can be used for other aspects in biomedical tissue engineering field.

Description

technical field [0001] The invention belongs to the technical field of biodegradable materials for medicine, and relates to the synthesis of polypropylene by catalyzing ring-opening copolymerization by using bionic organic guanidine salt—bicyclic guanidine acetate as a catalyst, lactide and serine morpholine diketone lactate as monomers. The lactide-serine morpholine dione is catalyzed to remove the O-benzyl group to obtain a biodegradable polymer lactic acid-serine copolymer with high biological safety (the molar content of serine in the copolymer is 1-5%). The synthesized lactic acid-serine copolymer is an amphiphilic functional-based biodegradable material, which is suitable as a carrier for targeted and controlled release drugs (especially water-soluble anticancer drugs), and can be used in many aspects in the field of biomedical tissue engineering . Background technique [0002] Protecting the ecological environment on which human beings depend and caring for human hea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/48C08G69/44C08G69/16A61K47/34A61L17/12A61L27/18A61L31/06
Inventor 李弘孔丽君宗绪鹏焦洁平
Owner NANKAI UNIV
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