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Organic bifunctional catalyst and preparation method thereof as well as stereoregular biodegradable polyester and preparation method thereof

A bifunctional catalyst, catalyst technology, applied in organic compound/hydride/coordination complex catalysts, organic chemistry, chemical instruments and methods, etc., can solve the problems of difficult physical and chemical properties, lack of functionalized side groups in polyester, etc. , to achieve the effect of optimized polymerization temperature, fast polymerization speed and low reaction temperature

Inactive Publication Date: 2021-07-09
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, polyesters obtained by this method often lack functionalized side groups, making it difficult to improve their physicochemical properties through post-modification.

Method used

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  • Organic bifunctional catalyst and preparation method thereof as well as stereoregular biodegradable polyester and preparation method thereof
  • Organic bifunctional catalyst and preparation method thereof as well as stereoregular biodegradable polyester and preparation method thereof
  • Organic bifunctional catalyst and preparation method thereof as well as stereoregular biodegradable polyester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0101] The preparation method of acid anhydride in O-carboxyl ring:

[0102]

[0103] Dissolve α-hydroxy acid (10mmol) in 30mL of anhydrous tetrahydrofuran, add 200mg of activated carbon, 6.7mmol of triphosgene, stir at room temperature for 20 hours, filter with suction, and recrystallize from diethyl ether three times to obtain O-carboxyl ring anhydride. Spectra and carbon spectra are characterized as follows.

[0104] (1) D-ManOCA: 1 H NMR (300MHz, CDCl 3 ):δ7.42-7.53(m,5H),6.02(s,1H). 13 C NMR (300MHz, CDCl 3 ): δ165.46, 148.15, 130.92, 129.67, 129.34, 126.26, 80.55. L-ManOCA: 1 HNMR and 13 C NMR is consistent with D-ManOCA.

[0105] (2)L-LacOCA: 1 H NMR (300MHz, CDCl 3 ):δ5.12(q,1H),1.71(d,3H). 13 C NMR (300MHz, CDCl 3 ): δ167.76, 148.20, 76.29, 16.60.

[0106] (3) L-Ser(Bn)OCA: 1 H NMR (300MHz, CDCl 3 ):δ7.26-7.40(m,5H),5.11(m,1H),4.60(m,2H,),3.91(m,2H,). 13 C NMR (CDCl 3 ,300MHz): δ165.66,148.55, 136.33,128.70,128.32,127.74,79.68,73.75,66.15.

[0107] ...

preparation Embodiment 1

[0119] The preparation of preparation example 1 catalyst 5

[0120]

[0121] Specific steps are as follows:

[0122] (1) Add 5.0g (33.8mmol) of 2,6-dichloropyridine, 643mg (3.38mmol) of copper iodide, and 587mg (6.76mmol) of lithium bromide to the Schlenk bottle, blow nitrogen for 30 minutes, and dissolve the mixture in 20mL at 0°C Anhydrous tetrahydrofuran, keep the temperature, dropwise add a tetrahydrofuran solution of tert-butylmagnesium chloride (50mL, 1M, 50mmol), stir for 12 hours, allow to gradually return to room temperature. After the reaction was completed, post-treatment was performed to obtain 2-tert-butyl-6-chloropyridine with a yield of 70%. With deuterated chloroform (CDCl 3 ) as a reagent with a 500 MHz nuclear magnetic resonance instrument (hydrogen spectrum, 1 H NMR), 125 MHz nuclear magnetic resonance (carbon spectrum, 13 C NMR) and high-resolution mass spectrometry characterized the structure of 2-tert-butyl-6-chloropyridine. 1 H NMR (500MHz, CDCl ...

preparation Embodiment 2

[0127] Preparation of Example 2 Catalyst 7

[0128]

[0129] Specific steps are as follows:

[0130] (1) Add 5.50 g (34 mmol) of 2,3-dichloro-5-methylpyridine, 1.30 g (6.8 mmol) of copper iodide, and 1.20 g (13.4 mmol) of lithium bromide to a Schlenk bottle, and pass nitrogen gas for 30 minutes, and the mixture Dissolve in 25mL of anhydrous tetrahydrofuran at 0°C, keep the temperature, add tert-butylmagnesium chloride solution in tetrahydrofuran (50mL, 1M, 50mmol) dropwise, stir for 12 hours, allow to gradually return to room temperature, and then reflux for 24h. After the reaction was completed, post-treatment was performed to obtain 2-tert-butyl-3-chloro-5-methylpyridine with a yield of 20%. With deuterated chloroform (CDCl 3 ) as a reagent with a 500 MHz NMR instrument (hydrogen spectrum, 1 H NMR) characterized the structure of 2-tert-butyl-3-chloro-5-methylpyridine. 1 H NMR (500MHz, CDCl 3 ):δ8.24(d,1H),7.44(d,1H),2.28(s,3H),1.48(s,9H).

[0131] (2) Add 0.90 g (4....

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Abstract

The invention relates to an organic bifunctional catalyst and a preparation method thereof, and stereoregular biodegradable polyester and a preparation method thereof. The organic bifunctional catalyst disclosed by the invention is obtained by reacting isocyanate or isothiocyanate with a pyridylamine compound. According to the catalyst, an O-carboxyl intracyclic anhydride monomer and a pyridine nucleophilic addition monomer of an amino acid source are activated by thiourea, and controllable ring opening polymerization can be performed on an OCA monomer under a mild condition by utilizing an amplification effect of adjacent groups, so that functional polyester with high isotacticity and controllable molecular weight is prepared. The solvent used for polymerization can be chloroform, toluene, dichloromethane and the like, the polymerization temperature range is 25-50 DEG C, and the stereoregularity is adjustable between 60% and 90%. Under the polymerization condition, the monomer conversion rate can reach 99% within 24-48 hours. The molecular weight of the obtained polyester is controllable, and the melting point reaches up to 150 DEG C. The molecular weight of the polyester is changed between 20,000 and 100,000, and the polyester has a wide prospect for industrial application.

Description

technical field [0001] The invention relates to the technical field of polymer material preparation, in particular to an organic bifunctional catalyst and a preparation method thereof, and a stereoregular biodegradable polyester and a preparation method thereof. Background technique [0002] With the development and progress of human society, the demand for polymer materials such as plastics, fibers, and rubbers is increasing year by year. However, with the continuous consumption of petroleum resources, the utilization of renewable resources has been put on the agenda. The significance of using renewable resources to synthesize polymer materials is self-evident. In addition, traditional polymer materials are poor in biodegradability and biocompatibility. Therefore, it is important to synthesize polymer materials with good degradability and biocompatibility. [0003] Polyα-hydroxy acid is an attractive biodegradable and biocompatible polymer widely used in biomedicine, agr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74C07D213/61C07D213/38B01J31/02C08G63/87C08G63/06
CPCC07D213/74C07D213/61C07D213/38B01J31/0271B01J31/0244C08G63/823C08G63/87C08G63/06
Inventor 陶友华李茂盛张帅
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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