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Unsaturated aliphatic polyester as well as preparation method and application thereof

An aliphatic polyester and unsaturated technology, which is applied in the field of medical materials and unsaturated aliphatic polyester, can solve the problems of poor photocuring ability, lack of reactive active sites in the main chain, and low biological activity, and achieve good elastic modulus The effect of volume and swelling properties, good biodegradability, and good biocompatibility

Inactive Publication Date: 2017-12-12
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, aliphatic polyesters have several major defects. First, aliphatic polyesters have poor hydrophilicity, low biological activity, and weak affinity and adhesion to cells.
Second, the main chain of aliphatic polyester lacks reactive sites, which limits the application of aliphatic polyester
However, the unsaturated double bond in the unsaturated aliphatic polyester reported in the above literature is located in the main chain, the reactivity is low, and the photocuring ability with other monomers containing unsaturated double bond is poor, so it cannot be applied as a tissue engineering scaffold

Method used

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  • Unsaturated aliphatic polyester as well as preparation method and application thereof
  • Unsaturated aliphatic polyester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Preparation of unsaturated aliphatic polyester

[0034] Take 10g (100mmol) of succinic anhydride, 7.1g (50mmol) of glycidyl methacrylate, 6.5g (50mmol) of n-butyl glycidyl ether, 0.83g (5mmol) of o-tert-butylhydroquinone and zinc isooctanoate 1.755g (5mmol), add 100mL ethyl acetate: butyl acetate = 1:1 volume ratio mixed solution to dissolve, under the protection of nitrogen, 110 ℃ ring-opening copolymerization reaction for 8h, remove the solvent to obtain unsaturated aliphatic polyester.

[0035] The weight-average molecular weight and number-average molecular weight of the obtained unsaturated aliphatic polyester were measured using Jasco Gulliver system (PU-980, CO-965, RI-930, and UV-1570) gel permeation chromatography. Equipped with polystyrene gel columns (Shodex columns K804, K805, and J806), using THF as eluent, polystyrene as standard calibration, measured at 30°C, the measurement result is: M w =16432, M n = 11255, PDI = 1.46.

[0036] (2) Preparation a...

Embodiment 2

[0065] (1) Preparation of unsaturated aliphatic polyester

[0066] Take succinic anhydride (10g, 100mmol), glycidyl methacrylate (50mmol, 7.1g), n-butyl glycidyl ether (50mmol, 6.5g), o-tert-butylhydroquinone (0.33g, 2mmol) and tetrabutylammonium bromide (0.64g, 2mmol), add 100mL of ethyl acetate: butyl acetate = 1:1 volume ratio mixed solution to dissolve, under the protection of nitrogen, 90 ℃ ring-opening copolymerization reaction for 5h, remove the solvent to get Unsaturated aliphatic polyester.

[0067] Gained unsaturated aliphatic polyester is detected by the method described in embodiment 1, and detection result is: M w =6028, M n =4982, PDI=1.21.

[0068] (2) Preparation and properties of photocurable hydrogel

[0069] (a) Formulation of photocurable hydrogel

[0070] 5 g of unsaturated aliphatic polyester prepared in step 1, 0.5 g of hydroxypropyl methacrylate, 0.5 g of hydroxyethyl methacrylate, 0.8 g of hydroxyethyl acrylate, 1.2 g of N,N-dimethylaminoethyl acr...

Embodiment 3

[0086] (1) Preparation of unsaturated aliphatic polyester

[0087] Take succinic anhydride (10g, 100mmol), glycidyl methacrylate (40mmol, 5.68g), n-butyl glycidyl ether (60mmol, 7.8g), o-tert-butylhydroquinone (1.33g, 8mmol) And zinc acetate (0.98g, 8mmol), add 100mL of ethyl acetate: butyl acetate = 1:1 volume ratio mixed solution to dissolve, under the protection of nitrogen, 120 ℃ ring-opening copolymerization reaction for 12h, remove the solvent to obtain unsaturated aliphatic polyester.

[0088] The obtained unsaturated aliphatic polyester is detected by the method described in Example 1, and the detection result is: M w =21611, M n = 12006, PDI = 1.80.

[0089] (2) Preparation and properties of photocurable hydrogel

[0090] (a) Formulation of photocurable hydrogel

[0091] 5 g of unsaturated aliphatic polyester prepared in step 1, 0.5 g of hydroxypropyl methacrylate, 0.5 g of hydroxyethyl methacrylate, 0.8 g of hydroxyethyl acrylate, 1.2 g of N,N-dimethylaminoethyl...

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Abstract

The invention relates to unsaturated aliphatic polyester. The polyester is formed by linearly and randomly arraying structure units shown in the chemical formula (I) and structure units shown in the chemical formula (II) at a molar ratio of 3:7-7:3, wherein the number-average molecular weight is 5,000-12,000, and the dispersibility index is 1.21-1.80; the unsaturated aliphatic polyester is obtained by ring-opening polyaddition of GMA (glycidyl methacrylate), n-butyl glycidyl ether and succinic anhydride. The unsaturated aliphatic polyester provided by the invention can be used for preparing a tissue engineering scaffold; the scaffold has better elasticity modulus and swelling property and is low in cytotoxicity, good in biocompatibility and high in cellular affinity.

Description

technical field [0001] The invention relates to an organic polymer compound, in particular to an unsaturated aliphatic polyester, which is suitable for medical materials. Background technique [0002] The main chain of aliphatic polyester is composed of aliphatic structural units connected by easily hydrolyzed ester bonds, and the main chain is flexible, and it is easy to be degraded by enzyme catalysis under the action of microorganisms. Therefore, aliphatic polyester is an important class of biomedical materials because of its good biocompatibility and biodegradability, and is widely used in the field of biomedicine, such as drug sustained release, surgical sutures, bone fixation materials, tissue engineering materials, etc. Commonly used aliphatic polyesters include polyglycolide (PGA), polylactide (PLA), glycolide-lactide copolymer (PLGA), polycaprolactone (PCL), and the like. There are currently two methods for the synthesis of aliphatic polyesters. The first is prep...

Claims

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Application Information

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IPC IPC(8): C08G63/58C08G63/78C08F283/01C08F220/28C08F220/18C08F220/34A61L27/52A61L27/50A61L27/18A61L27/16
CPCA61L27/16A61L27/18A61L27/50A61L27/52C08F283/01C08G63/58C08G63/78A61L2430/06C08G2210/00C08G2230/00C08L67/06C08L51/08C08F220/1806C08F220/1804C08F220/1808C08F220/34C08F220/281C08F220/286
Inventor 刘瑞源夏琦
Owner SOUTHERN MEDICAL UNIVERSITY
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