High-efficiency metal complex catalysts for the polymerization of caprolactone and lactide

A technology of metal complexes and metals, applied in the direction of magnesium organic compounds, calcium organic compounds, zinc organic compounds, etc., can solve the problems of wide product molecular weight distribution, narrow activity, narrow molecular weight distribution, etc.

Active Publication Date: 2011-12-07
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above catalyst systems either have high activity but wide product molecular weight distribution, or narrow molecular weight d

Method used

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  • High-efficiency metal complex catalysts for the polymerization of caprolactone and lactide
  • High-efficiency metal complex catalysts for the polymerization of caprolactone and lactide
  • High-efficiency metal complex catalysts for the polymerization of caprolactone and lactide

Examples

Experimental program
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preparation example Construction

[0018] Correspondingly, the present invention also provides a method for preparing the above two metal complexes, comprising:

[0019] Under anhydrous, oxygen-free and stirring conditions, the ligands and organometallic compounds MX shown in formulas (V), (VIa'), (VIb') and (VIc') 2 (VII) A substitution reaction occurs in an organic solvent to generate a metal complex of formula (I) or formula (II);

[0020]

[0021] Among them, R 1 and R 2 Each is independently hydrogen and C1-C30 chain alkane, phenyl or phenyl containing C1-C6 chain alkane group; X is C1-C30 straight-chain or branched-chain alkyl, or aliphatic amino;

[0022] M is the main group metal or transition metal.

[0023] As can be seen from the foregoing scheme, the reaction scheme of the above-mentioned metal complex is as follows:

[0024]

[0025] or

[0026] Since the metal complex is sensitive to air, the reaction should be carried out in an anhydrous, oxygen-free, and rapid stirring condition, an...

Embodiment 1

[0048] Example 1 Preparation of metal complexes A1~A6, B1~B6, F1~F6, J1~J6, K1~K6

[0049] Dissolve 1g of ligand 2-(6-methyl-2-pyridyl)-1-ethanol in 2ml of toluene to obtain a ligand solution; dissolve 7.4ml of dibutylmagnesium solution in 4ml of toluene to obtain dibutyl Magnesium solution in toluene.

[0050] Under anhydrous and oxygen-free conditions, at 25°C, slowly add the above-mentioned ligand solution dropwise to the toluene solution of dibutylmagnesium under rapid stirring and react for 1 hour to end the reaction. The reaction process is as follows:

[0051]

[0052] The reaction mixture was vacuum filtered to obtain a yellow viscous solid, which was washed with 10 ml of hexane solvent to obtain 1.09 g of white solid powder complex A1 with a yield of 69%.

[0053] The product that present embodiment is made carries out elemental analysis, and its molecular formula is C 12 h 19 MgNO: C, 66.24; H, 8.80; Mg, 11.17; N, 6.44; O, 7.35.

[0054] The preparation method...

Embodiment 2

[0059] Example 2 Preparation of metal complexes C1~C6, D1~D6, E1~E6

[0060] Dissolve 1 g of complex A prepared in Example 1 in 2 ml of toluene to obtain a ligand solution; dissolve 2.8 g of isopropanol in 3 ml of toluene to obtain a toluene solution of isopropanol.

[0061] Under anhydrous and oxygen-free conditions, slowly add the above ligand solution dropwise to the toluene solution of isopropanol under rapid stirring at 25°C and react for 1 hour to end the reaction. The reaction process is as follows:

[0062]

[0063] The reaction mixture was vacuum filtered to obtain a white viscous solid, which was washed three times with 10 ml of hexane solvent to obtain 0.91 g of white solid powder complex C1 with a yield of 90%.

[0064] The product that present embodiment is made carries out elemental analysis, and its molecular formula is C 11 h 17 MgNO 2 : C, 60.17; H, 7.80; Mg, 11.07; N, 6.38; O, 14.57.

[0065] The preparation method of complexes C2~C6 is the same as tha...

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Abstract

The invention provides four types of metal complexes. The four types of metal complexes have structures shown as a formula (I), a formula (II), a formula (III) or a formula (IV) described in the specification respectively, and have high independent catalytic activity on the polymerization of epsilon-caprolactone or a lactide monomer. The molecular weight distribution of a polymerization product is narrower. The invention further provides a catalyst composition, which consists of the metal complex with a structure shown as the formula (I), formula (II), formula (III) or formula (IV) and alcohol. The catalyst composition can be used for efficiently catalyzing polymerization of epsilon-caprolactone or the lactide monomer, and the molar ratio of the alcohol to the complex can be changed in a large range such as (0.1-100):1. The molecular weight of a polymer can be controlled by means of the molar ratio of the alcohol to the complex and is adjustable in the range 2,000-600,000, and the molecular weight distribution is 1.01-1.66.

Description

technical field [0001] The invention relates to the field of catalysts, in particular to metal complexes and catalyst compositions. Background technique [0002] Polyε-caprolactone (PCL) and polylactide (PLA) are both polyester biodegradable materials, and their monomers are derived from recyclable agricultural products such as corn and potatoes. Due to the excellent biodegradability of PCL and PLA, they are widely used in the production of disposable containers, tableware, films, fibers, clothing and auto parts, and are expected to replace traditional petrochemical resources to reduce environmental pollution. In addition, PCL and PLA also have the characteristics of good biocompatibility, non-toxicity and adjustable degradability, etc., the requirements of composite medical polymer materials, internal and external fixation of fractures, surgical sutures, tissue engineering scaffolds and drug slow release / Controlled-release carrier materials and other aspects have broad ap...

Claims

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Application Information

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IPC IPC(8): C07F3/02C07F3/04C07F3/06C08G63/08C08G63/83C08G63/82
Inventor 崔冬梅王洋
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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