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Application and preparation method of complex for catalyzing ring opening polymerization of lactide

A technology for catalyzing lactide and ring-opening polymerization, applied in the direction of magnesium organic compounds, chemical recovery, etc., can solve the problems of catalyst toxicity, product impurity, and high reaction conditions of chain extension method, and achieve narrow molecular weight distribution, simple preparation method, The effect of high catalytic activity

Active Publication Date: 2022-06-07
DALIAN UNIV OF TECH
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AI Technical Summary

Problems solved by technology

[0004] 1. Direct polycondensation method, which directly polymerizes lactic acid into polylactide. The catalyst used in this method is poisonous and difficult to remove, and the distribution of the product polylactide is difficult to control and the molecular weight is difficult to further increase;
[0005] 2. Chain extension method, including isocyanate coupling chain extension method, hexamethylene isocyanate coupling, chain extension method has high reaction conditions, high cost, and the product is impure, and separation requires more manpower, material resources, and financial resources;
[0006] 3. Indirect method, wherein the anionic ring-opening polymerization has the defects that side reactions are not easy to eliminate and high molecular weight products are not easy to obtain, and the cationic ring-opening polymerization has the defect that racemization reaction is not easy to occur
[0007] At present, the industrial production of PLA is mainly catalyzed by stannous octoate to catalyze the ring-opening polymerization of lactide. Studies have found that the polymer obtained by metal catalyst catalyzed lactide contains some metal residues. The tin element itself is toxic and harmful to the human body, which will limit Application of PLA in the field of food and medicine

Method used

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  • Application and preparation method of complex for catalyzing ring opening polymerization of lactide
  • Application and preparation method of complex for catalyzing ring opening polymerization of lactide
  • Application and preparation method of complex for catalyzing ring opening polymerization of lactide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] [CH 3 C(O)CHCN(CH 2 CH 2 O)CH 3 ] 4 Mg 4 Synthesis of (2a): In an argon atmosphere, take 1a (0.45 g, 3.1 mmol) and dissolve it in anhydrous and oxygen-free tetrahydrofuran, place the reaction in an ice-water bath at 0°C, and add dibutylmagnesium dropwise (2.5 mL, 1 M in n-hexane, 2.5 mmol), the reaction was stirred at 0 °C for 3 h to give a pale yellow clear solution. The solvent was dried in vacuum, washed three times with 6 mL of n-hexane to obtain a pale yellow powder, and the product was characterized by nuclear magnetic resonance and elemental analysis. Yield: 0.68 g (33%). 1 H-NMR (400MHz, CDCl 3 ): δ=4.71(s, 4H, [OC(C-H)CN]), 3.60–3.56(m, 4H, NCH 2 CH 2 ), 3.44 (br, 4H, NCH 2 CH 2 ), 3.25-3.22 (m, 4H, NCH 2 CH 2 ), 3.04-2.97 (m, 4H, NCH 2 CH 2 ), 1.84(s, 12H, CH 3 CO), 1.78 (s, 12H, CH 3 EN). 13 C-NMR (400MHz, CDCl 3 ): δ=179.06(C=O), 170.71(C-N), 96.82([OC(C-H)CN]), 61.36(CH 2 O), 51.46 (NCH 2 ), 27.41 (CH 3 CO), 21.30 (NCCH 3 ).Anal.Calcd...

Embodiment 2

[0027] [CH 3 C(O)CHCN(CH 2 CH 2 CH 2 O)CH 3 ] 4 Mg 4 Synthesis of (2b): In an argon atmosphere, 1b (0.73 g, 4.6 mmol) was dissolved in tetrahydrofuran treated with anhydrous and anoxic, and dibutylmagnesium (3.7 mL, 1 M inn- hexane, 3.7 mmol) and the reaction was stirred at 55 °C overnight to give a milky cloudy solution. The reaction was cooled to room temperature, the layers were statically separated, filtered to obtain a yellow filtrate, the solvent was vacuum dried, washed three times with 6 mL of n-hexane to obtain a yellow powder, and the product 2b was characterized by NMR. 1 H-NMR (400MHz, CDCl 3 ): δ=4.66(s, 4H, [OC(C-H)CN]), 3.53–3.49(m, 8H, NCH 2 CH 2 CH 2 ), 3.42-3.31 (m, 8H, NCH 2 CH 2 CH 2 ), 1.83(s, 12H, CH 3 CO), 1.81 (s, 12H, CH 3 CN), 1.52-1.45 (m, 8H, NCH 2 CH 2 CH 2 ).

Embodiment 3

[0029] [CF 3 C(O)CHCN(CH 2 CH 2 O)CH 3 ] 4 Mg 4 Synthesis of (2c): In an argon atmosphere, 1c (0.56 g, 2.8 mmol) was dissolved in anhydrous and oxygen-free tetrahydrofuran, the reaction was placed in an ice-water bath at 0°C, and dibutylmagnesium was added dropwise (2.3 mL, 1 M in n-hexane, 2.3 mmol), the reaction was stirred at 0 °C for 3 h to give a clear, colorless solution. The solvent was vacuumed to dryness, washed three times with 6 mL of n-hexane to obtain a white powder, and the product 2c was characterized by NMR. 1 H-NMR (400MHz, CDCl 3 ): δ=5.25(s, 4H, [OC(C-H)CN]), 3.59-3.54(m, 4H, NCH 2 CH 2 ), 3.46-3.40 (m, 4H, NCH 2 CH2 ), 3.38-3.36 (m, 4H, NCH 2 CH 2 ), 3.09-3.02 (m, 4H, NCH 2 CH 2 ), 1.93(s, 12H, CH 3 EN).

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Abstract

The invention belongs to the field of complex preparation and application, and discloses application and a preparation method of a complex for catalyzing lactide ring-opening polymerization. In an argon environment, Mg (n-Bu) 2 is dropwise added into the beta-ketimine ligand solution within the temperature range of 0-25 DEG C, a reaction is conducted for 3 h within the temperature range of 0-55 DEG C, and the tetranuclear N-alkoxy-beta-ketimine magnesium complex is obtained. The tetranuclear N-alkoxy-beta-ketimine magnesium complex prepared by the method is applied to catalysis of lactide ring opening polymerization. Under solution and body conditions, lactide polymerization can be catalyzed without the participation of a cocatalyst to prepare polylactide. The catalyst is simple in preparation method, novel in structure and high in catalytic activity. The polymer obtained by the reaction is narrow in molecular weight distribution and controllable in molecular weight.

Description

technical field [0001] The invention belongs to the field of complex preparation and application, in particular to the application of a tetranuclear N-alkoxy-β-ketimine magnesium complex in catalyzing the ring-opening polymerization of lactide and a preparation method thereof. Background technique [0002] Polylactide (PLA) is a polymer with good biocompatibility and biodegradability. PLA has good tensile strength and ductility, and it can be decomposed into carbon dioxide and water in vivo, which makes it a It is an ideal biomedical material, which can be used as drug delivery, surgical suture material and artificial tissue material, so it has great research potential. [0003] The existing methods for synthesizing PLA include: [0004] 1. Direct polycondensation method, directly polymerizing lactic acid into polylactide, the catalyst used in this method is poisonous, difficult to remove, and the product polylactide distribution is difficult to control, and the molecular w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/83C08G63/08C07F3/02
CPCC08G63/83C08G63/823C08G63/08C07F3/02Y02P20/584
Inventor 彭瑛王欣宇耿晓云王娇
Owner DALIAN UNIV OF TECH
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