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Salicyldenaminato schiff base metal complex catalyst as well as preparation method thereof and application thereof

A technology of salicylaldimine mat and metal complex, which is applied in the field of salicylaldimine Schiff base metal complex catalyst and its preparation, and can solve the problem of high polymer

Active Publication Date: 2016-09-28
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Another object of the present invention is to provide a salicylaldimine Schiff base metal complex catalyst as a catalyst in the self-polymerization of diisocyanate to prepare polyisocyanate curing agents with controllable molecular weight distribution, which not only solves the problem of direct chemical synthesis of curing agents The high polymer in the method is high, and at the same time, a product with excellent molecular weight distribution can be obtained and the free monomer in the product is less than 0.3wt%.

Method used

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  • Salicyldenaminato schiff base metal complex catalyst as well as preparation method thereof and application thereof
  • Salicyldenaminato schiff base metal complex catalyst as well as preparation method thereof and application thereof
  • Salicyldenaminato schiff base metal complex catalyst as well as preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of Catalyst I

[0036] In the synthesis kettle, according to the formula weight ratio, dissolve 200 parts of 3-chloro-o-hydroxybenzaldehyde in 2000 parts of methanol and add 1 part of p-toluenesulfonic acid (TsOH) as a catalyst, and slowly add to the system at 60 ° C. 70 parts of ethylamine were added dropwise, and the reaction was maintained for 4h. After the reaction, methanol and excess ethylamine were evaporated at 80° C. under normal pressure, and the remaining product was recrystallized and purified with ethanol solvent / toluene.

[0037] The NMR and mass spectrometric analysis of the product is as follows: 1 H NMR (CDCl 3 ,400MHz):δ 8.54(1H,s),7.54-7.02(3H,m),5.35(1H,br s),3.59(2H,t,J=8.0Hz),1.18(3H,q,J=8.0 Hz); 13 C NMR (CDCl 3 ,100MHz):δ159.8,157.5,134.9,130.2,126.0,124.3,122.8,53.3,16.3; HRMS(ESI):Calcd for C 9 h 11 ClNO[M+H] + 184.0524, Found: 184.0529;

[0038] In the synthesis kettle, 38 parts of 2-chloro-N-ethyl salicylaldimine, 18 part...

Embodiment 2

[0041] Preparation of Catalyst II

[0042] In the synthesis kettle, according to the formula weight ratio, dissolve 250 parts of 2,4-di-tert-butylbenzaldehyde in 2000 parts of ethanol and add 2.5 parts of p-toluenesulfonic acid (TsOH) as a catalyst, and slowly 100 parts of aniline was added dropwise to the system, and the reaction was maintained for 6 hours. After the reaction, the ethanol was evaporated at 200pa and 40°C, and the remaining product was purified by recrystallization with methanol / toluene.

[0043] The NMR and mass spectrometric analysis of the product is as follows: 1 H NMR (CDCl 3 ,400MHz):δ 8.87(1H,s),7.52-7.06(7H,m),5.35(1H,br s),1.35(9H,s),1.34(9H,s); 13 C NMR (CDCl 3 ,100MHz):δ160.0,153.7,152.0,138.4,137.7,130.0,128.3,127.2,122.3,117.7,34.5,34.4,31.6,31.3; HRMS(ESI): Calcd for C 21 h 28 NO[M+H] + 310.2165, Found: 310.2164;

[0044] In the synthesis kettle, according to the formula weight ratio, 44 ​​parts of 2,4-di-tert-butyl-N-phenyl salicylaldimi...

Embodiment 3

[0047] Preparation of Catalyst III

[0048] In the synthesis kettle, according to the formula weight ratio, 200 parts of 4-methoxy o-hydroxybenzaldehyde was dissolved in 2000 parts of methanol and 1 part of p-toluenesulfonic acid (TsOH) was added as a catalyst. 75 parts of ethylamine were added dropwise to the system, and the reaction was maintained for 4.5 hours. After the reaction, ethanol and ethylamine were evaporated at 200pa and 40°C, and the remaining product was purified by recrystallization with ethanol / toluene.

[0049] The NMR and mass spectrometric analysis of the product is as follows: 1 H NMR (CDCl 3 ,400MHz):δ 8.54(1H,s),7.71-6.48(3H,m),5.35(1H,br s),3.83(3H,s),3.59(2H,t,J=8.0Hz),1.18( 3H,q,J=8.0Hz); 13 C NMR (CDCl 3 ,100MHz): δ164.3, 162.1, 157.5, 133.4, 116.9, 107.0, 103.4, 55.8, 53.3, 16.3; HRMS (ESI): Calcd for C 10 h 14 NO 2 [M+H] + 180.1019, Found: 180.1022;

[0050] In the synthesis kettle, 36 parts of 3-methoxy-N-ethyl salicylaldimine, 18 parts...

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Abstract

The invention relates to a salicyldenaminato schiff base metal complex catalyst and a preparation method thereof. The catalyst comprises the following components: (A) a salicyldenaminato schiff base ligand, (B) a transition metal compound which can be coordinated with the salicyldenaminato schiff base ligand, and (C) alkali metal or alkaline-earth metal salt. The catalyst is used for catalyzing self-polymerization of diisocyanate in order to prepare a polyisocyanate curing agent, the problem of higher content of high polymers in the curing agent which is prepared by a direct synthesis method is solved, and at the same time products with excellent molecular weight distribution are obtained, and free monomers in the products are lower than 0.3wt%.

Description

technical field [0001] The invention relates to a salicylaldimine Schiff base metal complex catalyst and its preparation method and application, which can be used to prepare polyisocyanate curing agent with controllable molecular weight distribution. Background technique [0002] For a long time, there have been a lot of reports on the literature and patents on the preparation of isocyanurate-containing polyisocyanate compounds. Aliphatic and aromatic isocyanate trimers are also widely used as primer materials or in the field of polyurethane elastomers and polyurethane foams. [0003] Isocyanate monomers are generally not directly used in the coatings industry due to their high volatility and toxicity. From the point of view of occupational health and hygiene, converting it into a trimer with low free monomer content is one of the main application forms at present. At present, the reduction of free monomers is mainly achieved by thin film evaporation or the direct synthesi...

Claims

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Application Information

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IPC IPC(8): B01J31/22C08G18/79
CPCB01J31/2217B01J2231/14B01J2531/828B01J2531/845B01J2531/847C08G18/794C08G2115/02
Inventor 王暖程尚永华王玉启石滨华卫琦黎源乔小飞梁广荣
Owner WANHUA CHEM GRP CO LTD
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