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Method for catalyzing glycolide polymerization with asymmetric aluminum complex containing o-phenylenediamine group

A technology of o-phenylenediamine and aluminum complexes, applied in the fields of compounds containing group 3/13 elements of the periodic table, chemical instruments and methods, organic chemistry, etc., can solve the problems of non-renewability and non-degradability, etc. Achieve the effects of various catalyst structures, high stereoselectivity, and controllable molecular weight

Active Publication Date: 2020-09-04
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] While traditional polymer plastics that use petroleum as raw materials bring convenience to people's production and life, they also have two fatal shortcomings: non-renewability and non-degradability

Method used

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  • Method for catalyzing glycolide polymerization with asymmetric aluminum complex containing o-phenylenediamine group
  • Method for catalyzing glycolide polymerization with asymmetric aluminum complex containing o-phenylenediamine group
  • Method for catalyzing glycolide polymerization with asymmetric aluminum complex containing o-phenylenediamine group

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The structural formula of the synthesized ligand is the above formula (A), where R is hydrogen, and the reaction process is as follows: add 0.40 g of unilaterally protected o-phenylenediamine (a) and an equimolar amount of salicylaldehyde into 20 mL of methanol, and heat to reflux After 12 hours of reaction, after the reaction was completed, it was cooled and filtered, washed with cold methanol, filtered, collected, dried and weighed to obtain 0.50 g of solid, with a yield of 87.7%.

[0043] The product obtained is characterized, and the results are as follows:

[0044] 1 H NMR (400 MHz, CDCl 3 ) δ 12.86 (s, 1H, O H ), 8.42 (s, 1H, Ar H C=N),7.85 (m, 2H, Ar– H ), 7.64 (d, J = 7.0 Hz, 1H, Ar– H ), 7.56 (m, 1H, Ar– H ), 7.44(m, 3H, Ar– H ), 7.32 (m, 2H, Ar– H ), 6.96 (m, 4H, Ar– H ).

[0045] HRESI-MS: m / z cacld.C 21 h 14 N 2 o 3 [M-H] - ; 341.0926, found: 341.0924.

[0046] It can be seen from the above characterization results that the obtained produ...

Embodiment 2

[0048] The structural formula of the synthesized ligand is the above formula (A), where R is a methyl group, and the reaction process is as follows: 0.30 g of unilaterally protected o-phenylenediamine (a) and an equimolar amount of 3,5-dimethyl salicylaldehyde Add 20 mL of methanol, heat to reflux for 12 hours, cool and filter after the reaction, wash with cold methanol, filter, collect, dry and weigh to obtain 0.40 g of solid, with a yield of 85.1%.

[0049] The product obtained is characterized, and the results are as follows:

[0050] 1 H NMR (400 MHz, CDCl 3 ) δ 12.72 (s, 1H, O H ), 8.40 (s, 1H, Ar H C=N),7.80 (m, 2H, Ar– H ), 7.66 (m, 2H, Ar– H ), 7.15 (m, 3H, Ar– H ), 6.92 (s, 1H, Ar– H ), 2.15 (s, 3H, ArC H 3 ), 2.04 (s, 3H, ArC H 3 ). HRESI-MS: m / z ccld. C 23 h 18 N 2 o 3 [M-H] - ; 369.1238, found: 369.1238.

[0051] It can be seen from the above characterization results that the obtained product is the ligand in which R is a methyl group in the above...

Embodiment 3

[0053] The structural formula of the synthesized ligand is the above formula (A), where R is bromine, and the reaction process is as follows: add 0.35 g of unilaterally protected o-phenylenediamine (a) and 3,5-dibromosalicylaldehyde in 20 In mL methanol, heated to reflux for 12 hours, after the reaction was completed, cooled and filtered and washed with cold methanol, filtered, collected, dried and weighed to obtain 0.66 g of solid, with a yield of 90.4%.

[0054] The product obtained is characterized, and the results are as follows:

[0055] 1 H NMR (400 MHz, CDCl 3 ) δ 12.64 (s, 1H, O H ), 8.344 (s, 1H, Ar H C=N),7.86 (d, J = 7.2 Hz, 1H, Ar– H ), 7.68 (m, 3H, Ar– H ), 7.42 (m, 2H, Ar– H ), 7.36(m, 1H, Ar– H ), 7.10 (m, 3H, Ar– H ).

[0056] HRESI-MS: m / z cacld.C 21 h 12 Br 2 N 2 o 3 [M-H] - ; 496.9134, found: 496.9136.

[0057] It can be seen from the above characterization results that the obtained product is the ligand in which R is bromine in the above f...

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Abstract

The invention discloses a method for catalyzing polymerization of glycolide by using an asymmetric aluminum complex containing an o-phenylenediamine group, and the method comprises the following steps: mixing a catalyst, an organic solvent and a benzyl alcohol co-catalyst with the glycolide for ring-opening polymerization under anhydrous oxygen-free inert-gas protection conditions, and after the reaction, treating the reaction product to obtain polyglycolide; wherein the catalyst is the asymmetric aluminum complex containing the o-phenylenediamine group. The self-developed asymmetric aluminumcomplex containing the o-phenylenediamine group is used as the catalyst, the catalyst is simple in preparation method, the cost is low, the yield is high, the catalyst structure is varied, metal center aluminum is coordinated with bivalent N, N, O and O of a ligand, and the catalyst has high catalytic activity, high stereoselectivity and fast reaction rate. The obtained polymer is a benzyloxy-terminated polymer with narrow molecular weight distribution, controllable molecular weight and high yield, and can meet the needs of the market.

Description

technical field [0001] The invention relates to a method for catalyzing the polymerization of glycolide, in particular to a method for catalyzing the polymerization of glycolide by using an asymmetric aluminum complex containing o-phenylenediamine groups. Background technique [0002] While traditional polymer plastics that use petroleum as raw materials bring convenience to people's production and life, they also have two fatal shortcomings: non-renewability and non-degradability. Because petroleum is a non-renewable resource, the rapid development of polymer plastic materials that rely on petroleum raw materials is greatly restricted, and polymer plastic materials are difficult to degrade, and a large amount of polymer plastic material waste has accumulated in real life for a long time. Pollution has also gradually increased. Finding renewable resources to replace petroleum and developing environmentally friendly and biodegradable new materials have become the development...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/08C08G63/84C07F5/06
CPCC07F5/066C08G63/08C08G63/823
Inventor 姚伟高爱红张永芳王洪宾
Owner UNIV OF JINAN
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