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Preparation method of bio-based copolyester containing modifiable functional group

A copolyester and bio-based technology, which is applied in the fields of polymer materials and chemical engineering, can solve the problems of unfavorable biomedical applications, high biological toxicity, and low atom utilization

Active Publication Date: 2020-02-18
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalyst used in this method is a transition metal catalyst, which has high biological toxicity and is not easy to remove from the product, which is not conducive to the application in biomedicine
In addition, the molar ratio of α-methylene-γ-butyrolactone structural units in the copolyester obtained in this method is not more than 40%, and the conversion rate of α-methylene-γ-butyrolactone is only 7% , the atomic utilization is very low

Method used

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  • Preparation method of bio-based copolyester containing modifiable functional group
  • Preparation method of bio-based copolyester containing modifiable functional group
  • Preparation method of bio-based copolyester containing modifiable functional group

Examples

Experimental program
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Effect test

Embodiment 1

[0044] (0.15mmol, 16.2mg) benzyl alcohol, (0.15mmol, 179.7mg) hexa[tri(dimethylamine) phosphazene]tripolyphosphazene, (0.45mmol, 113.7mg) 1-cyclohexyl-3- (4-Chlorophenyl) urea was dissolved in 6.0mL tetrahydrofuran, placed in a low-temperature cold bath at -50°C and stirred for 10 minutes, and (7.5mmol, 0.66mL) α-methylene-γ-butyrolactone and ( 7.5mmol, 0.84mL) ε-caprolactone was added into the reaction tube at the same time. The reaction was carried out under nitrogen protection for 2 h, and 10 drops of acetic acid was added to terminate the reaction. The reaction mixture was dissolved in 9 mL of chloroform, poured into 60 mL of methanol, centrifuged and precipitated to obtain a polymer, which was characterized by NMR as a ring-opened copolyester, namely PMBL-co-PCL. The number average molecular weight measured by CPC is 10.6kg / mol, the molecular weight distribution is 1.13, and the GPC spectrogram is as follows figure 2 shown. Compared with Comparative Example 1, there i...

Embodiment 2

[0046] (0.05mmol, 5.41mg) benzyl alcohol, (0.05mmol, 59.9mg) hexa[tri(dimethylamine) phosphazene]tripolyphosphazene, (0.15mmol, 32.75mg) 1-cyclohexyl-3- Phenylurea was dissolved in 2.0mL tetrahydrofuran, placed in a low-temperature cold bath at -40°C and stirred for 10 minutes, and (2.5mmol, 0.22mL) α-methylene-γ-butyrolactone and (2.5mmol, 0.28mL ) ε-caprolactone was added to the reaction tube at the same time. The reaction was carried out under nitrogen protection for 1 h, and 10 drops of benzoic acid were added to terminate the reaction. The reaction mixture was dissolved in 3 mL of chloroform, poured into 40 mL of methanol, centrifuged and precipitated to obtain a polymer, which was characterized by nuclear magnetic resonance as a ring-opened copolyester, namely PMBL-co-PCL, and its number-average molecular weight measured by CPC was 12.8 kg / mol, the molecular weight distribution is 1.30, and the GPC spectrum is as follows figure 2 shown.

Embodiment 3

[0048] (0.10mmol, 4.6mg) ethanol, (0.10mmol, 119.8mg) hexa[three (dimethylamine) phosphazene] tripolyphosphazene, (0.20mmol, 57.3mg) 1-cyclohexyl-3-( 4-Trifluoromethylphenyl)urea was dissolved in 4.0ml tetrahydrofuran, placed in -50°C low-temperature cold bath and stirred for 10min, and (5mmol, 0.44mL) α-methylene-γ-butyrolactone and (5mmol, 0.56mL) ε-caprolactone mixed solution was added to the reaction tube. The reaction was carried out under nitrogen protection for 4 h, and 10 drops of acetic acid was added to terminate the reaction. The reaction mixture was dissolved in 4 mL of chloroform, poured into 40 mL of methanol, centrifuged and precipitated to obtain a polymer, which was characterized by NMR as a ring-opened copolymer, namely PMBL-co-PCL. The number average molecular weight recorded by CPC is 9.6kg / mol, and the molecular weight distribution is 1.12, and its GPC spectrum is as follows figure 2 shown.

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Abstract

The invention discloses a preparation method of a bio-based copolyester containing a modifiable functional group, and a random copolyester of alpha-methylene-gamma-butyrolactone, epsilon-caprolactone,delta-valerolactone, and gamma-butyrolactone prepared thereby. A binary catalysis system, which is composed of a strong alkali and a co-catalyst (urea or thiourea), is used to catalyze selective ring-opening co-polymerization of alpha-methylene-gamma-butyrolactone and other cyclic monomers to prepare the bio-based copolyester containing a modifiable functional group. The prepared bio-based copolyester can meet the application requirements of the biomedicine field, and the physical property of the bio-based copolyester can be modulated in a wider range.

Description

technical field [0001] The invention relates to the fields of polymer materials and chemical engineering, in particular, the invention relates to a preparation method of a bio-based copolyester containing a modifiable functional group. Background technique [0002] Aliphatic polyesters are considered as environmentally friendly green polymer materials due to their good degradability and biocompatibility, and have a wide range of applications in the medical field, including absorbable sutures, bone screws, tissue engineering scaffolds, and drug delivery carrier etc. Common aliphatic polyesters include polycaprolactone, polylactic acid, polyglycolic acid, polyhydroxyalkanoate, and the like. However, some characteristics of these polyesters limit their application in the field of biomedicine. For example, due to its own hydrophobicity and semi-crystalline nature, polycaprolactone degrades slowly in the body, and it takes 2 to 4 years to completely degrade it, so it cannot be ...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G63/87C08G63/83
CPCC08G63/08C08G63/87C08G63/823C08G63/83
Inventor 沈勇王瑞赵志超李志波
Owner QINGDAO UNIV OF SCI & TECH
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