A class of star-shaped comb-shaped fluorescent polylactic acid and its preparation method

A star-shaped comb-shaped, polylactic acid technology is applied in the field of star-shaped comb-shaped fluorescent polylactic acid and its preparation, which can solve the problems of harsh reaction conditions, low biological activity, limited application, poor controllability, etc., and achieves a simple functionalization method, Improve polymer properties, fluorescence development efficiency, mild and efficient synthesis reaction conditions

Active Publication Date: 2021-09-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the low reactivity and biological activity of the most commonly used polylactic acid (PLA) material itself limits its further application in biological response, tracking, and regulation of degradation and release. Therefore, functional modification and chemical Modification has become one of the most important research directions in the field of biomedical materials
Commonly used functional modification methods include monomer modification and post-functionalization of the main chain. The process is relatively complicated, the reaction conditions are harsh, and the controllability is poor. Therefore, the functional modification of the initiator and the end modification become crucial. important

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation of hydroxylated star-shaped liquid polybutadiene: using classic ionic polymerization method, using cyclohexane as solvent, n-butyllithium as initiator, and silicon tetrachloride as coupling agent to prepare star-shaped liquid polybutadiene ene, the number average molecular weight of polybutadiene before coupling is 1600g / mol, and the number average molecular weight of product star-shaped liquid polybutadiene after coupling is 6515g / mol (using gel permeation chromatography GPC test), molecular weight distribution index (PDI for short, the same below) is 1.11. Add 3.6g of the above-mentioned star-shaped liquid polybutadiene into a 250mL reactor, and dissolve it in 150mL of toluene, turn on the stirring and temperature, add 1.25g of 98% formic acid when the temperature rises to 40°C, and add 3.02g of formic acid dropwise within 30min The 30% hydrogen peroxide of 1g, wash with deionized water to neutrality after reacting 2h, remove solvent by rotary evaporation,...

Embodiment 2

[0018] Preparation of star-shaped comb polylactic acid: normal temperature and pressure, under the protection of inert gas argon, 3 g of L-lactide, 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD ) 0.016g (according to the mol ratio of TBD and monomer is 1:200 to calculate), the hydroxylated star-shaped liquid polybutadiene initiator 0.98g that synthesizes in the embodiment 1 joins in the 10mL dichloromethane, at 25 ℃ After 1 hour of reaction, benzoic acid was added to terminate the reaction, and star-shaped comb polylactide was obtained after treatment. Product M n 14×10 4 g / mol, PDI is 1.39; the hydroxyl initiation efficiency is 48.7%, and the number of arms is 22.

Embodiment 3

[0020] Preparation of star-shaped comb-shaped polylactic acid: under normal temperature and pressure, under the protection of inert gas argon, 5 g of racemic lactide, nitrogen methyl-1,5,7-triazabicyclo[4.4.0]decane -5-ene 0.025g (wherein the molar concentration of racemic lactide monomer is calculated as 1:200), the hydroxylated star-shaped liquid polyisoprene initiator 1g synthesized in Example 1 is added in 10mL toluene, After reacting for 10 h at -20°C, benzoic acid was added to terminate the reaction, and star-shaped comb polylactide was obtained after treatment. Product M n 2.1×10 4 g / mol, PDI is 1.28; hydroxyl initiation efficiency is 91%, and the number of arms is 12.

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Abstract

A class of star-shaped comb-shaped fluorescent polylactic acid and its preparation method belong to the technical field of polymer materials. Its structure is C-(Pf)n, wherein C is a star-shaped macromolecular initiator residue, P is polylactic acid, and f is a fluorescent function group, n is the degree of star-shaped branching, n is greater than or equal to 3; the number-average molecular weight of the star-shaped comb-shaped fluorescent polylactic acid is 1×10 4 -50×10 4 g / mol, the number average molecular weight per arm is 0.1×10 4 -2×10 4 g / mol; the star-shaped macromolecular initiator is a star-shaped hydroxylated polymer, the number of hydroxyl groups is 8-60, and the number-average molecular weight is 0.1×10 4 -2×10 4 g / mol; the fluorescent functional group is a small fluorescent molecule containing a carboxyl group, and the capping rate of the small fluorescent molecule is 10%‑100%. First, a star-shaped hydroxylated polymer initiator was synthesized by an active anion reaction, and an organic base was used as a catalyst to catalyze the ring-opening polymerization of lactide, and a class of star-shaped comb-shaped polylactic acid was grafted with a fluorescent functional group to prepare Star-shaped comb-like hyperbranched fluorescent polylactic acid. The functionalization method is simple, the synthesis reaction conditions are mild, and the star-shaped comb-like highly branched structure effectively improves the performance of the polymer and the fluorescence imaging efficiency.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a class of star-shaped comb-shaped fluorescent polylactic acid and a preparation method thereof. Background technique [0002] Aliphatic polyester is renewable, biodegradable, biocompatible and absorbable, and is an environmentally friendly green polymer material, which has a wide range of applications in the field of biomedicine, especially as a controlled release of drugs. drug delivery carrier. Due to the complexity and diversity of polymer structures, polymer materials can be endowed with more superior properties by changing the structure and composition of polymers to expand their application range. The development trend of polymer structure is from star structure to branched structure. Most of the currently synthesized biodegradable aliphatic polyesters have star-shaped, star-shaped, dendritic and hyperbranched structures, and most of them have disadvantages such ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/91C08G63/08C08G63/87
CPCC08G63/08C08G63/823C08G63/912
Inventor 冷雪菲李杨边宇飞魏志勇王艳色
Owner DALIAN UNIV OF TECH
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