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A kind of Schiff base zinc compound, its preparation method and the preparation method of polylactic acid

A technology of zinc and Schiff base compounds, which is applied in the field of polymers and can solve problems such as random linking sequences of chain segments

Active Publication Date: 2017-01-11
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] At present, in the industrial production of polylactic acid produced by catalyzing the ring-opening polymerization of lactide, stannous octoate is mainly used as a catalyst. Although stannous octoate has the advantage of low cost, there is no choice in catalytic racemic lactide polymerization. properties, only polymers with random linking order of chain segments can be obtained

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  • A kind of Schiff base zinc compound, its preparation method and the preparation method of polylactic acid
  • A kind of Schiff base zinc compound, its preparation method and the preparation method of polylactic acid
  • A kind of Schiff base zinc compound, its preparation method and the preparation method of polylactic acid

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[0045] The present invention also provides a kind of preparation method of Schiff base zinc compound, comprises the following steps:

[0046] A) reacting a Schiff base having a structure shown in formula 2 with an organic zinc compound in a solvent to obtain a Schiff base zinc compound having a structure shown in formula 3;

[0047]

[0048] Among them, R 1 and R 2 independently selected from -H, alkyl, halogen or -NO 2 ;

[0049] R 3 , R 4 and R 5 independently selected from -H or -CH 3 ;

[0050] B) reacting the Schiff base zinc compound having the structure of formula 3 with a hydroxyl-containing compound in a solvent to obtain a Schiff base compound having the structure shown in formula 1;

[0051]

[0052] The R' is an alkoxy group or -OCH 2 One of Ph, the Ph is phenyl.

[0053] In the present invention, the Schiff base with the structure shown in formula 2 is reacted with the organic zinc compound in a solvent to obtain the Schiff base zinc compound with ...

Embodiment 1

[0087]Dissolve 3.05g of amino alcohol in 20mL of ethanol, slowly add dropwise 50mL of ethanol solution containing 6.1g of salicylaldehyde, and reflux the resulting mixed solution for 14h to obtain a reaction solution; rotary evaporation removes most of the solvent in the reaction solution, The obtained reaction product was purified by column chromatography, and the eluent of the column chromatography was n-hexane and ethyl acetate with a volume ratio of 1:1 to obtain a Schiff base.

[0088] The Schiff base that the present invention will obtain carries out nuclear magnetic resonance spectrum 1 HNMR (300.00MHz, CDCl 3 ) analysis, the results show: δ=8.21(s, NCH 1H), 7.24(t, ArH 1H), 7.13(d, ArH 1H), 6.86(d, ArH 1H), 6.79(t, ArH1H), 3.78(t , NCH 2 C 2H),3.60(t,CCH 2 OH 2H). 13 CNMR (100MHz, CDCl 3 )δ=166.67 (NCH), allbenzene ring: 162.12, 132.62, 131.60, 118.44, 118.33, 117.29; 61.67 (NCCOH), 60.95 (COH). This shows that the Schiff base obtained in this embodiment has the s...

Embodiment 2

[0090] Dissolve 3.05g of amino alcohol in 20mL of ethanol, slowly dropwise add 50mL of ethanol solution containing 9.6g of 3,5-dichlorosalicylaldehyde, and reflux the resulting mixed solution for 14h to obtain a reaction solution; rotary evaporation removes the reaction solution. most of the solvent in the solution, and the resulting reaction product was recrystallized with dichloromethane to obtain a Schiff base.

[0091] The present invention carries out the proton nuclear magnetic resonance spectrum analysis to the Schiff base that obtains 1 HNMR (300.00MHz, d 6 -DMSO), the results are as follows:

[0092] δ=14.46(s, OH 1H), 8.51(s, NCH 1H), 7.56(d, ArH 1H), 7.42(d, ArH 1H), 3.67(m, NCH 2 C, CCH 2 OH 4H). 13 CNMR (100MHz,d 6 -DMSO) δ=166.50 (NCH), all ozone ring: 165.02, 133.44, 130.88, 125.48, 116.85, 116.65; 60.15 (COH), 56.25 (NCCOH). This shows that the Schiff base obtained in this embodiment has formula 2 The structure shown, where R 1 and R 2 Simultaneously -C...

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Abstract

The present invention provides a Schiff base zinc compound, which has a structure shown in Formula 1, wherein R1 and R2 are independently selected from -H, alkyl, halogen or -NO2; R3, R4 and R5 are independently selected from - H or -CH3; R' is an alkoxy group or -OCH2Ph, and the Ph is a phenyl group. The Schiff base zinc compound with the structure shown in formula 1 provided by the present invention has on the one hand a bimetallic center Schiff base catalyst with a larger molecular structure and larger steric hindrance, which enhances the selectivity of lactide ring-opening polymerization , which improves the regularity of the spatial structure of the polymerization product; on the other hand, the introduction of the bimetallic center can enhance the reactivity of the catalyst in the polymerization. Experimental results show that the yield of polylactic acid prepared by the method provided by the invention can reach 90%, and the stereoregularity (Pm) of the obtained polylactic acid can reach 0.60.

Description

technical field [0001] The invention belongs to the technical field of polymers, and in particular relates to a Schiff base zinc compound, a preparation method thereof and a preparation method of polylactic acid. Background technique [0002] Polylactic acid is a chemically synthesized biodegradable material, which is widely used in packaging materials, biomedicine and pharmaceutical industries. The synthesis of polylactic acid usually adopts two methods, namely, ring-opening polymerization of lactide (cyclic dimer of lactic acid) and direct polymerization of lactic acid. Among them, polymer polylactic acid generally adopts the method of ring-opening polymerization of lactide, and a large number of documents and patents have carried out relevant reports on the ring-opening polymerization of lactide, such as the U.S. Patent No. US5235031 and the U.S. Patent No. US5357034 patent. [0003] Lactide is divided into three stereoisomers: L-lactide (LLA), D-lactide (DLA) and meso-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/06B01J31/22C08G63/08C08G63/83
CPCB01J31/2217B01J2231/14B01J2531/0238B01J2531/26C07F3/003C07F3/06C08G63/08C08G63/83
Inventor 庞烜段然龙李想孙志强张涵陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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