Preparation method of polylactone

A technology of polylactone and ester compounds, which is applied in the field of polylactone preparation, can solve problems such as the inability to realize lactide solution polymerization, and achieve the effects of large commercial application potential, low loading capacity, and narrow molecular weight distribution

Active Publication Date: 2019-06-07
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2013, the research group reported that it can catalyze the ring-opening polymerization of carbonate, but it cannot realize the solution polymerization of lactide, and needs to add an additional base to catalyze the ring-opening polymerization of lactide (Macromolecules, 2013,46(5):1772 -1782)

Method used

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  • Preparation method of polylactone
  • Preparation method of polylactone
  • Preparation method of polylactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Add carbocation salt 1 (8.9mg, 0.05mmol, 1.0equiv), benzyl alcohol (5.2μL, 0.05mmol, 1.0equiv) and δ-valerolactone (150mg, 1.5mmol, 30equiv) into the reaction flask, and use 1.5 mL of dichloromethane was dissolved, and under the protection of argon, the reaction was stirred at room temperature for 2 hours. Add triethylamine to terminate the reaction, pour the reactant into methanol after concentration, filter the precipitate and dry to constant weight to obtain 102mg white solid with a conversion rate of 95%, and the number average molecular weight Mn of polyδ-valerolactone is 4.3kg mol -1 , the dispersion PDI is 1.07; its hydrogen spectrum is as follows figure 1 Shown: 1 H NMR (300MHz, CDCl 3 ):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 2

[0049] Carbocation salt 4 (17.2mg, 0.05mmol, 1.0equiv), benzyl alcohol (5.2μL, 0.05mmol, 1.0equiv) and trimethylene carbonate (153mg, 1.5mmol, 30equiv) were added to the reaction flask, under air Under the conditions, the bulk reaction was stirred at 50° C. for 2 hours. Add triethylamine 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 conversion rate of 92%. The number average molecular weight Mn of polytrimethylene carbonate is 3.5 kg mol -1 ; Dispersion PDI is 1.12; its hydrogen spectrum data such as image 3 Shown: 1 H NMR(300MHz,Chloroform-d)δ(ppm),7.16~7.30(m,5H,aromatic),4.13~4.31(m,2H,(ArCH 2 CH 2 CH 2 -); m,4H×n,(-OCH 2 CH 2 CH 2 O-)n),3.73(t,2H,-CH 2 OH), 2.71(t,2H,ArCH 2 -),2.00~2.08(m,2H,(ArCH 2 CH 2 -); m,2H×n,(-OCH 2 CH 2 -)), 1.91(q,2H,-CH 2 CH 2 OH).

Embodiment 3

[0051] Add carbocation salt 2 (26.8mg, 0.05mmol, 1.0equiv), benzyl alcohol (5.2μL, 0.05mmol, 1.0equiv) and ε-caprolactone (171mg, 1.5mmol, 30equiv) into the reaction flask, and use 1.5 mL of toluene was dissolved, and under the protection of argon, the reaction was stirred at room temperature for 6 hours. Triethylamine was added to terminate the reaction, the reactant was concentrated and poured into methanol, the precipitate was filtered and dried to constant weight to obtain 94.5 mg of white solid with a conversion rate of 53%. From the MALDI-ToF MS spectrum of polycaprolactone ( Figure 10 ) data, there is only one ion peak cluster with Poisson distribution in the spectrogram, and the average difference between adjacent ion peaks is 114m / z, which is exactly the molecular weight of the ε-caprolactone unit, which also has the adjacent mass difference of 114m / z Other series of ion peaks are different signals due to the addition of other types of ions. The molar mass of two hi...

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Abstract

The invention discloses a preparation method of a polylactone, and relates to the technical field of macromolecule materials. The method uses an initiator alcohol or amine to initiate the ring openingof a cyclic lactone monomer or a cyclic lactide monomer or a cyclic carbonate monomer, and uses a stable carbon cationic salt as an organic catalyst to initiate the ring-opening polymerization of a small molecular monomer to obtain the polylactone. By adopting the technical scheme of the method, the catalyst has the beneficial effects of low load and high efficiency, plays the role of controllingmolecular weight and / or stereochemistry of the polymer, and shows high reactivity. In particular, the new catalyst has better practicability than a catalyst used in the prior art, has less catalyst consumption, has a wide range of catalytic monomers, and has no metal residue.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, in particular to a preparation method of polylactone. 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. In terms of catalysts for the ring-opening polymerization of lactide, polylactic acid was prepared by ring-opening polymerization of lactide using metal-containing catalysts in the early stage. Howe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/84C08G63/08
Inventor 郭凯刘晶晶李振江徐嘉熙郭天佛高宇张磊姚志威张婵
Owner NANJING TECH UNIV
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