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Nitrogen-bridged bis(phenolate) yttrium dibenzyl oxygen compound and preparation and application thereof

A technology of dibenzyl oxide compound and bisaryloxy yttrium is applied in the field of double active center type yttrium complexes to achieve the effect of narrow molecular weight distribution

Inactive Publication Date: 2009-12-02
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report on the controllable homo(co)polymerization of ε-caprolactone and L-lactide catalyzed by nitrogen-bridged bisaryloxy rare earth metal complexes with dual active centers as a single-component catalyst

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: p-C 6 H 4 [CH 2 OYL(THF)] 2 (Substituents at positions 3 and 5 on the aromatic ring of L are methyl groups) Synthesis

[0034] In LYNPh 2 (THF) (3.42 g, 5 mmol) in THF solution, add p-dibenzyl alcohol p-C 6 H 4 (CH 2 OH) 2 (0.35 g, 2.5 mmol), the color of the system remained basically colorless, and the reaction was carried out overnight at room temperature. Most of the solvent was removed, and 20 ml of n-hexane was added and left to stand overnight. A large number of colorless crystals were precipitated. The clear liquid was removed by centrifugation. The solid was recrystallized with a mixed solvent of n-hexane and tetrahydrofuran to precipitate a large amount of colorless crystals. 2.56 g (2.20 mmol) , 88%).

Embodiment 2

[0035] Example 2: p-C 6 H 4 [CH 2 OYL(THF)] 2 (The 3 and 5 substituents on the aromatic ring of L are tert-butyl) synthesis

[0036] In LYNPh 2 (THF) (4.26 g, 5 mmol) in THF solution, add p-dibenzyl alcohol p-C 6 H 4 (CH 2 OH) 2 (0.35 g, 2.5 mmol), the color of the system remained basically colorless, and the reaction was carried out overnight at room temperature. Remove most of the solvent, add 20 ml of n-hexane and let stand overnight. A large number of colorless crystals are precipitated. The clear liquid is removed by centrifugation. The solid is recrystallized with a mixed solvent of n-hexane and tetrahydrofuran to precipitate a large amount of colorless crystals. 3.42 g (2.28 mmol) , 91%).

Embodiment 3

[0037] Example three: p-C 6 H 4 [CH 2 OYL(THF)] 2 (The substituents at positions 3 and 5 on the aromatic ring of L are methyl) catalyze the controlled ring-opening polymerization of ε-caprolactone

[0038] Add 0.60 ml (5.42 mmol) of ε-caprolactone in a dehydrated and deoxygenated polymerization bottle with a stirrer, then add 1.90 ml of toluene with a syringe, and add 0.5 ml of toluene solution of the catalyst with a syringe under stirring (6.02× 10 -3 Millimole·ml -1 ). Polymerize for 90 minutes at room temperature, terminate the reaction with alcohol containing 5% hydrochloric acid, precipitate the polymer with industrial alcohol, and dry it under vacuum to constant weight to obtain 0.61 g of polycaprolactone, with a yield of 99%. The theoretical number average molecular weight of the polymer is 201,100 [M n (calcd)=(M w of ε-CL)×[ε-CL] / [I]×(polymer yield)=114×1800×99%], GPC measured number average molecular weight (M n ) Is 196,800, and the molecular weight distribution (M w / M...

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PUM

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Abstract

The invention discloses a nitrogen-bridged bis(phenolate) yttrium dibenzyl oxygen compound and preparation and application thereof. A bridged bis(phenolate) lanthanide complex is the nitrogen-bridged bis(phenolate) yttrium dibenzyl oxygen compound, of which the chemical formula is p-C6H4[CH2OYL(THF)]2, wherein Y refers to lanthanide yttrium; and L refers to a nitrogen-bridged bis(phenolate) complex; L=Me2NCH2CH2N{CH2-(2-O-C6H2-R-3,5)}2, wherein 3 position and 5 position of an aromatic ring are provided with alkyl group substituents R, and R is selected from C1-C4 saturated alkyl. The double active center type nitrogen-bridged bis(phenolate) yttrium dibenzyl oxygen compound is synthesized simply and conveniently, not only can be used as a single-component catalyst under a mild condition to catalyze ring opening polymerization of epsilon-Hexalactone and L-lactide controllably with high activity, but also can initiates copolymerization of the two monomers to generate ABA type block copolymer.

Description

Technical field [0001] The invention relates to a rare earth metal complex, in particular to a double active center type yttrium complex with a nitrogen-bridged bisaryloxy group as an auxiliary ligand and bridged by a p-dibenzyloxy group and its catalytic application. Background technique [0002] Aliphatic polyester is a type of biodegradable polymer material, which can be degraded under physiological conditions, and the degradation products are non-toxic. Therefore, it has been used clinically as a biological tissue compatible material (see: Hayashi, T. Prog. Polym. Sci., 1994, 19, 663). Polycaprolactone has high solubility, low melting point, and is compatible with a variety of polymers, and can be used as a polymer plasticizer, etc. (see: Deanin, RD, Zhang, ZBJ Vinyl Technol. 1984, 6, 18) . Polylactic acid is also widely used in drug controlled release systems due to its characteristics (see: Zhang, XC; McAuley, KB; Goss en, MFAJ Control. Release 1995, 34, 175), orthopedic fi...

Claims

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Application Information

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IPC IPC(8): C07F5/00C08G63/84C08G63/08
Inventor 孙宏枚宋丰奎闫春辉姚英明
Owner SUZHOU UNIV
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