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Novel multidentate monophenol oxygen-based ligand calcium complex as well as preparation method and application thereof

A multi-dentate monophenolic calcium and multi-dentate monophenolic oxygen technology is applied in the application field of lactone ring-opening polymerization, which can solve the problem of low activity and achieve high catalytic activity, stable properties and wide application prospects. Effect

Inactive Publication Date: 2010-06-30
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The ring-opening polymerization under the catalysis of calcium complex has good controllability, its PDI=1.1~1.3., and the molecular weight increases linearly with the monomer conversion rate, but the activity is low

Method used

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  • Novel multidentate monophenol oxygen-based ligand calcium complex as well as preparation method and application thereof
  • Novel multidentate monophenol oxygen-based ligand calcium complex as well as preparation method and application thereof
  • Novel multidentate monophenol oxygen-based ligand calcium complex as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Calcium Complex C1

[0034] Under argon protection, the ligand 2-{N-(2-methoxybenzyl)N-[2-(N,N-dimethylamino)ethyl]}aminomethyl was added to a 100mL Schlenk bottle Base-4-methyl-6-tert-butylphenol (0.384g), toluene 15mL, add Ca[N(SiMe 3 ) 2 ] 2 (2THF) (0.504g), stirred at room temperature, and recrystallized to obtain colorless crystals (0.409g, yield 65%), code name C1.

[0035]

[0036] 1 H NMR (C 6 D. 6 , 400MHz): δ7.37(d, 1H, J=2.4Hz, ArH), 6.88(td, 1H, J=7.7Hz, J=1.8Hz, ArH), 6.83(d, 1H, J=2.0Hz, ArH), 6.71(td, 1H, J=7.4Hz, J=1.2Hz, ArH), 6.65(dd, 1H, J=7.6Hz, J=2.0Hz, ArH), 6.62(d, 1H, J=8.4 ArH), 3.71 (br, 1H, Ar-CH 2 -N), 3.55(s, 4H, CH 3 O-Ar overlapped by 1H of Ar-CH 2 -N signal), 2.94 (br, 1H, Ar-CH 2 -N), 2.46(s, 4H, Ar-CH 3 overlapped by 1H of N-CH 2 -Ar signal), 2.08-1.96 (m, 2H, CH 2 CH 2 ), 1.92 (s, 3H, NCH 3 ), 1.83(s, 9H, C(CH 3 ) 3 ), 1.79-1.62 (m, 1H, CH 2 CH 2 ), 1.36 (s, 3H, NCH 3 ), 1.18-1.15 (m, 1H, CH 2 CH ...

Embodiment 2

[0038] Synthesis of Calcium Complex C2

[0039] Under argon protection, add the ligand 2-{N-(5-methyl-3-tert-butyl-2-methoxybenzyl)-N-[2-(N,N- Dimethylamino)ethyl]}aminomethyl-4,6-dicumylphenol (0.637g), toluene 15mL, add Ca[N(SiMe 3 ) 2 ] 2 (2THF) (0.504g), stirred at room temperature, and recrystallized to obtain colorless crystals (0.556g, yield 60%), code C2.

[0040]

[0041] Anal.Calcd.for C 49 h 77 N 3 o 2 Si 2 Ca(C 7 h 8 ): C, 72.49; H, 9.25; N, 4.53. Found: C, 71.94; H, 9.02; N, 4.24%.

Embodiment 3

[0043] Synthesis of Calcium Complex C3

[0044] Under argon protection, add the ligand 2-[N-(2-methoxybenzyl)-N-(2-methoxyethyl)]aminomethyl-4-methyl in a 100mL Schlenk bottle -6-tert-butylphenol (0.371g), toluene 15mL, add Ca[N(SiMe 3 ) 2 ] 2 (2THF) (0.504g), stirred at room temperature, and recrystallized to obtain colorless crystals (0.400g, yield 70%). Codenamed C3.

[0045]

[0046] 1 H NMR (C 6 D. 6 , 400MHz): δ7.39(d, 1H, J=1.2Hz, ArH), 6.89(td, 1H, J=7.8Hz, J=1.2Hz, ArH), 6.84(s, 1H, ArH), 6.69( t, 1H, J=7.4Hz, ArH), 6.63(d, 1H, J=7.2Hz, ArH), 6.54(d, 1H, J=8.4Hz, ArH), 3.96(d, 1H, J=12.4Hz , N-CH 2 -Ar), 3.86(d, 1H, J=11.2Hz, N-CH 2 -Ar), 3.46(s, 3H, CH 3 O-Ar), 3.02(s, 3H, CH 2 CH 2 OCH 3 ), 2.98-2.95 (m, 1H, CH 2 CH 2 ), 2.46(s, 3H, Ar-CH 3 ), 2.44-2.30 (m, 3H, CH 2 CH 2 ), 2.16 (d, 1H, J=12.8Hz, Ar-CH 2 -N), 1.86(s, 9H, C(CH 3 ) 3 ), 1.27 (d, 1H, J=11.6Hz, Ar-CH 2 -N), 0.34(s, 18H, N(Si(CH 3 ) 3 ) 2 ). 13 C{ 1 H}(C 6 D. 6 , 100MHz): ...

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Abstract

The invention discloses a novel multidentate monophenol oxygen-based ligand calcium complex as well as a preparation method and an application thereof. The preparation method comprises the following steps of carrying out reaction of a ligand L and Ca [N(SiMe3)2]2(2THF) and then collecting target products from a reaction product. The calcium complex contains asymmetric multidentate monophenol oxygen-based ligand, is an effective lactone ring-opening polymerization catalyst, can be used for ring-opening polymerization of caprolactone, lactide and the like and can obtain polymers with certain isotacticity when rac-lactide is catalyzed to carry out the ring opening polymerization. The multidentate monophenol oxygen-based calcium complex has obvious advantages of easy availability of raw materials, simple synthesis route, easy separation and purification, relatively stable property and high catalytic activity and can satisfy the needs of industrial departments. A general formula of the structure thereof is shown as follows.

Description

technical field [0001] The invention relates to a class of metal calcium complexes containing multidentate monophenolic oxygen ligands and the application of such complexes in lactone ring-opening polymerization. Background technique [0002] ε-caprolactone (ε-CL, ε-Caprolactone) and lactide (LA, Lactide) are cyclic lactones containing ester groups, which are often used as monomers for polymerization reactions. The products obtained by ring-opening polymerization-poly Caprolactone (PCL, Polycaprolactone) and polylactic acid (PLA, Polylactic acid; also known as polylactide, Polylactide) have biodegradability, excellent biocompatibility, plasticity, easy processing and molding, and are regarded as the most promising Advanced biodegradable materials have potential application value in medical and health care, daily necessities, food packaging, clothing and other fields. Therefore, the catalytic ring-opening polymerization of lactide and caprolactone has attracted widespread at...

Claims

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Application Information

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IPC IPC(8): C07F19/00C08G63/83C08G63/08
Inventor 马海燕王丽英徐绍安
Owner EAST CHINA UNIV OF SCI & TECH
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