Method for preparing polylactone

A technology of polylactone and caprolactone is applied in the fields of organic catalysis and polymer materials, which can solve the problems of unsatisfactory ring-opening polymerization effect, high catalyst price and high catalyst conditions, and achieves enhanced process feasibility and high reaction selectivity. , the effect of fast aggregation

Active Publication Date: 2015-12-30
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Some catalysts are not ideal for ring-opening polymerization of lactones (Endo et al., Macromolecules, 2000, 33, 4316-4320), and some catalysts are expensive (Toyoji Kakuchi et al., Macromolecules, 2011, 44, 1999-2005), and some Sensitive to moisture in the air (Toyoji Kakuchi et al., Macromolecules, 2010, 43, 7090-7094), some catalysts use too high conditions and the effect is not ideal (Armando Co'rdova et al., Advanced Synthesis & Catalysis, 2004, 346, 1087-1089)

Method used

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  • Method for preparing polylactone
  • Method for preparing polylactone
  • Method for preparing polylactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] γ-Resorcinol (0.0154g, 0.1mmol, 1.0equiv), δ-valerolactone (0.27ml, 3.0mmol, 30equiv) and benzyl alcohol (10.3μL, 0.1mmol, 1.0equiv) were added to the reaction flask, Dissolved with 1.0ml of dichloromethane, under the protection of argon, stirred and reacted at room temperature for 18 hours, concentrated the reactant and poured it into methanol, filtered the precipitate and dried to constant weight to obtain a white polyvalerolactone product, the conversion rate It is 94% (proton nuclear magnetic resonance spectrum, 400MHz, CDCl 3 ), the number average molecular weight M of polyvalerolactone n 3090gmol -1 (Proton NMR spectrum, 400MHz, CDCl 3 ), the dispersion PDI is 1.08 (molecular exclusion chromatography, Waterscolumn: 5mm, 300 × 7.8mm, tetrahydrofuran mobile phase, 0.7mLmin -1 , polystyrene as standard), 1 HNMR (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 ),...

Embodiment 2

[0030]γ-Resorcinol (0.0154g, 0.1mmol, 1.0equiv), ε-caprolactone (0.33ml, 3.0mmol, 30equiv) and propynyl alcohol (5.8μL, 0.1mmol, 1.0equiv) were added to the reaction flask , dissolved with 1.0ml of toluene, under the protection of argon, stirred and reacted at room temperature for 24 hours, the reactant was concentrated and poured into ethanol, the precipitate was filtered and dried to constant weight to obtain a white polyvalerolactone product, and the conversion rate was 93%, the number average molecular weight of polyvalerolactone M n 4320gmol -1 , the dispersion PDI is 1.06, 1 HNMR (300MHz, CDCl 3 ):δ(ppm),1.39(m,2H×n,(–CH 2 CH 2 CH 2 CH 2 CH 2 –) n ),1.63(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 ),3.65(t,2H,J=6.6Hz,CH 2 CH 2 OH), 4.06(t, 2H×n, J=6.6Hz, (–CH 2 CH 2 O–) n ),5.12(s,2H,ArCH 2 O), 7.23–7.39 (m, 5H, aromatic); polyε-caprolactone 1 HNMR spectrum see figure 2 .

Embodiment 3

[0032] γ-Resorcinol (0.0154g, 0.1mmol, 1.0equiv), butyl caprolactone (3.3ml, 30.0mmol, 300equiv) and N-(2-hydroxyethyl)maleimide (14.112g , 0.1mmol, 1.0equiv) into the reaction flask, dissolved with 2.0ml of tetrahydrofuran, under the protection of argon, stirred at room temperature for 48 hours, then concentrated the reactant and poured it into ether, precipitated and filtered and dried to constant weight, Obtain white polyvalerolactone product, conversion rate is 82%, the number average molecular weight M of polybutyl position caprolactone n 20800gmol -1 , the dispersion PDI is 1.18.

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Abstract

The invention discloses a preparation method of polylactone and belongs to the technical field of organocatalysis and high polymer materials. By the use of a catalyst (gamma-resorcylic acid) which is natural and safe, is not sensitive to the environment, is commercially available and is cheap and has an ideal catalytic effect, polyvalerolactone and polycaprolactone are prepared at 0-200 DEG C in the presence or in the absence of a solvent, so as to obtain a high polymer biodegradable material having large molecular weight and narrow dispersity and containing no metal impurities. Thus, defects of a catalyst commonly used in industry in aspects of safety, price, sensitivity to the environment and catalytic effect are overcome, and a simple, mild, effective and cheap polymerization method is provided. A high polymer material prepared by the method can be applied in fields of drug carrier, nanoreactor, film, material interface and the like, has biodegradability and is an environmentally-friendly material.

Description

technical field [0001] The invention belongs to the technical field of organic catalysis and macromolecular materials, and in particular relates to a method for synthesizing polylactone with a cheap and easy-to-obtain catalyst. Background technique [0002] Since the 1930s, the synthesis and application of polymers have become increasingly important. At present, polymer materials are ubiquitous in our lives, such as polystyrene, polyolefin, polyvinyl chloride, etc. However, these common polymer materials are difficult to degrade in nature, and their waste even causes serious pollution to the environment. Therefore, the study of biodegradable polymer materials has far-reaching significance. [0003] Aliphatic polyester polymers are currently the most studied type of biodegradable polymer materials, which can be gradually degraded in water, enzymes or microbial environments, helping to solve the current increasingly serious environmental problems, and the small molecules obt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/08C08G63/87C08G63/685
Inventor 郭凯徐嘉熙李振江刘晶晶徐松泉潘先福刘佳琦
Owner NANJING UNIV OF TECH
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