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Polylactone preparation method

A technology of polylactone and cyclic lactone, applied in the field of polylactone, can solve the problems of complicated synthesis of bifunctional catalysts, and achieve the effects of wide application type, simple synthesis and narrow molecular weight distribution

Active Publication Date: 2015-04-22
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the types of hydrogen bonds are limited, and there are only a small number of bifunctional catalysts, and the synthesis of these bifunctional catalysts is relatively cumbersome.

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Square amide (Sq1) (26.8mg, 0.05mmol, 1.0equiv), (-)-spartine (11.7mg, 0.05mmol, 1.0equiv), benzyl alcohol (5.2μL, 0.05mmol, 1.0equiv) and L - Lactide (216mg, 1.5mmol, 30equiv) was added to the reaction flask, dissolved with 1.5mL of dichloromethane, and stirred at room temperature for 2 hours under the protection of Ar. Add benzoic acid to terminate the reaction, concentrate the reactant and pour it into methanol, filter the precipitate and dry to constant weight to obtain 148 mg of white solid with a transformation rate of 98.2%. The number average molecular weight of polylactic acid is M n 4330g mol -1 , the dispersion PDI is 1.05, 1 H NMR (300MHz, CDCl 3 ):δ(ppm)1.57(m,3H×n,(–CH 3 ) n ),4.34(m,–CH(CH 3 )OH), 5.13-5.21(q, 1H×n-1, J=7.0, –CH(CH 3 )O–; 2H, ArCH 2 O–),7.33-7.34(m,5H,aromatic).

Embodiment 2

[0041]Square amide (Sq1) (26.8mg, 0.05mmol, 1.0equiv), (-)-spartenine (11.7mg, 0.05mmol, 1.0equiv), benzyl alcohol (5.2μL, 0.05mmol, 1.0equiv) and δ - Add valerolactone (150mg, 1.5mmol, 30equiv) into the reaction flask, dissolve it with 1.5mL of dichloromethane, and react with stirring at room temperature for 2 hours under the protection of Ar. Add benzoic acid to terminate the reaction, concentrate the reactant and pour it into methanol, filter the precipitate and dry to constant weight to obtain 102 mg of white solid with a transformation rate of 93.5%. The number average molecular weight of polylactic acid M n 4320g mol -1 , the dispersion PDI is 1.07; 1 H NMR (300MHz, CDCl3): δ (ppm) 1.68 (m, 2H×n, (–CH 2 CH 2 CH 2 O–) n ),1.70(m,2H×n,(–COCH 2 –CH 2 CH 2 –) n ),2.34(t,2H×n,J=6.8Hz,(–OCOCH 2 CH 2 –) n ),3.65(t,2H,J=6.1Hz,–CH 2 CH 2 OH), 4.08(t, 2H×n, J=5.5Hz, (–CH 2 CH 2 O-) n ),5.12(s,2H,ArCH 2 O), 7.32–7.39 (m, 5H, aromatic).

Embodiment 3

[0043] Square amide (Sq1) (26.8mg, 0.05mmol, 1.0equiv), (-)-spartenine (11.7mg, 0.05mmol, 1.0equiv), benzyl alcohol (5.2μL, 0.05mmol, 1.0equiv) and ε - Caprolactone (171 mg, 1.5 mmol, 30 equiv) was added to the reaction flask, dissolved with 1.5 mL of dichloromethane, and stirred at room temperature for 6 hours under the protection of Ar. Add benzoic acid to terminate the reaction, concentrate the reactant and pour it into methanol, filter the precipitate and dry to constant weight to obtain 94.5 mg of white solid with a transformation rate of 92.3%. The number average molecular weight of polylactic acid is M n 3530g mol -1 ;, the dispersion PDI is 1.10; 1 H NMR (CDCl 3 ),δ(ppm),1.38(m,2H×n,(–CH 2 CH 2 CH 2 CH 2 CH 2 –) n ),1.65(m,2H×n,(–CH 2 CH 2 CH 2 O–) n ),1.68(m,2H×n,(–COCH 2 CH 2 –CH 2 –) n ),2.31(t,2H×n,J=7.3Hz,(–OCOCH 2 CH 2 –) n ),3.66(t,2H,J=6.6Hz,–CH 2 CH 2 OH), 4.06(t, 2H×n, J=6.9Hz, (–CH 2 CH 2 O–) n ),5.12(s,2H,ArCH 2 O),7.32–7.40(m,5H,ar...

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Abstract

The invention discloses a polylactone preparation method. The method includes the specific steps that ring opening of cyclic lactone monomer or cyclic carbonate monomer is initiated by initiator alcohol or initiator amine, ring opening polymerization of micromolecule monomer is initiated under the catalyzing action of organic catalysts, and polylactone is obtained. Compared with an existing catalyzing system, the polylactone preparation method has the obvious advantages of being moderate, efficient, wide in source range, simple in synthesis, multiple in category, wide in range, free of metal and the like.

Description

technical field [0001] The invention belongs to the technical field of organic catalysis and polymer materials, and specifically relates to a polylactone method. Background technique [0002] Polylactic acid, polyε-caprolactone, polyδ-valerolactone and polycarbonate are biodegradable and bioabsorbable polymer materials, which can be easily blended with other polymer materials to improve the degradability of polymer materials new. As a fully degradable and environmentally friendly material derived from renewable resource crops, it has attracted widespread attention and research from people all over the world. [0003] There have been a lot of researches on the preparation methods of polylactones, among which ring-opening polymerization with cyclic lactones is a method that has been studied more. As far as the catalysts for the ring-opening polymerization of lactide are concerned, in the early stage, metal-containing catalysts were used to carry out ring-opening polymerizati...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G63/87C08G64/30
Inventor 李振江刘晶晶吴文卓崔赛德徐嘉熙陈诚智绪
Owner NANJING UNIV OF TECH
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