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A kind of isocyanate polymerization catalyst and its preparation method, and its method for preparing polyisocyanate

A technology of polyisocyanate and isocyanate, applied in organic compound/hydride/coordination complex catalysts, chemical instruments and methods, physical/chemical process catalysts, etc. Low conversion rate and other problems, to achieve the effect of mild reaction process, simple preparation process and high monomer conversion rate

Active Publication Date: 2019-09-03
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Patents GB837120 and US3211703 propose to use organic alkali metals, heavy metals and tertiary amines as catalysts for the preparation of polyisocyanates. The products are mainly trimer structures. However, in these reactions, the amount of metal catalysts is large, and they are easy to separate out during use, resulting in product occurrence. Turbidity; tertiary amine catalysts have too low reactivity at low temperature and need to be kept at a higher temperature to maintain high activity, and it is easy to cause ammonia odor in the product
[0005] Patent DE1150080 proposes to use quaternary ammonium base as a catalyst for preparing polyisocyanate, but under the action of this catalyst, the reaction process is prone to runaway temperature, which leads to uncontrollable reaction process and cannot be widely used in production
[0006] Patent US7001973 discloses a benzyl-substituted quaternary ammonium carboxylate catalyst, using the catalyst to catalyze the reaction to obtain a light-colored polyisocyanate, but the trimer structure is the main structure, and the amount of catalyst used in the reaction is relatively large. Excessive heat release, difficult to control
[0007] The patent US4912210 involves pyridine compounds and alkylaminophosphine catalysts, and the prepared products are mainly dimers, basically no trimer structure, and the monomer conversion rate is low
[0008] Patent US8097691 mentions phosphine-containing heterocyclic compounds, which can prepare products containing both trimer and dimer structures, but the catalyst preparation process is complicated and the catalyst activity is low at low temperatures

Method used

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  • A kind of isocyanate polymerization catalyst and its preparation method, and its method for preparing polyisocyanate
  • A kind of isocyanate polymerization catalyst and its preparation method, and its method for preparing polyisocyanate
  • A kind of isocyanate polymerization catalyst and its preparation method, and its method for preparing polyisocyanate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Under the condition of isolating moisture and nitrogen protection, mix 1:1.2 (molar ratio) N,N-dimethylethylenediamine and dichloromethylphosphine in a reaction flask, gradually heat to 110°C and mix with each other, and keep stirring. React at 170°C for 1.5 hours to obtain a light yellow viscous liquid, then recrystallize and separate with ethyl acetate and petroleum ether at a mass ratio of 1:1 to obtain 1# catalyst, the reaction equation is as follows:

[0042]

[0043] The characterization data of 1# catalyst are as follows:

[0044] 1 HNMR(400M,TMS):δ2.67(t,4H),2.43(s,6H),1.18(s,3H)

[0045] 13 CNMR (100M, TMS): δ57.8, 38.6, 10.3

[0046] [M+H] ⊕ :133.0889(ESI)

Embodiment 2

[0048] Under the condition of isolating moisture and nitrogen protection, mix N,N-diethylethylenediamine and dichloromethylphosphine in a reaction flask at a molar ratio of 1:1.1, gradually heat to 130°C and mix with each other, and keep stirring. React at 180°C for 3 hours to obtain a light yellow viscous liquid, then use ethyl acetate and petroleum ether with a mass ratio of 1:1 as a solvent to recrystallize and separate to obtain 2# catalyst, the reaction equation is as follows:

[0049]

[0050] The characterization data of 2# catalyst are as follows:

[0051] 1 HNMR (400M, TMS): δ2.96 (t, 4H), 2.67 (s, 4H), 1.18 (s, 3H),

[0052] 1.02(s,6H)

[0053] 13 CNMR (100M, TMS): δ55.6, 43.3, 14.4, 10.9

[0054] [M+H] ⊕ :161.1129(ESI)

Embodiment 3

[0056] Under the condition of isolation of water and nitrogen protection, mix 1:1.3 (molar ratio) N,N-dimethylethylenediamine and dichloromethoxyphosphine in a reaction flask, gradually heat to 140°C and mix with each other, and keep stirring , reacted at 180°C for 2.5 hours to obtain a light yellow viscous liquid, and then recrystallized and separated with ethyl acetate and petroleum ether with a mass ratio of 1:1 to obtain 3# catalyst. The reaction equation is as follows:

[0057]

[0058] The characterization data of 3# catalyst are as follows:

[0059] 1 HNMR (400M, TMS): δ3.51 (s, 3H), 2.67 (s, 4H), 2.43 (s, 6H),

[0060] 13 CNMR (100M, TMS): δ58.9, 54.4, 37.4

[0061] [M+H] ⊕ :149.0765(ESI)

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Abstract

The invention relates to an isocyanate polymerization catalyst, a preparation method thereof, and a method for preparing polyisocyanate. The catalyst has a 1,3,2-diazaphospholane structure, and the preparation method is simple and feasible. The catalyst is used to prepare polyisocyanate, the catalyst has low initiation temperature, mild reaction process and high monomer conversion rate, and the prepared polyisocyanate product has both trimer and dimer structures.

Description

technical field [0001] The invention relates to a catalyst for isocyanate polymerization, a preparation method of the catalyst, and a method for preparing polyisocyanate. Background technique [0002] The general structure of polyisocyanate is trimer and dimer. The trimer is a six-membered ring structure formed by the trimerization of isocyanate monomers. The structure has good thermal stability, especially the aliphatic or alicyclic trimer has anti-yellowing properties, but this structure has a high viscosity; the dimer is formed by dimerization of isocyanate monomers, and the structure has weak stability Based on the trimer structure, but can reduce the viscosity of the system. [0003] The key to preparing polyisocyanate lies in the selection of catalysts. The main catalysts include organic alkali metals and heavy metals, alkylaminophosphines, tertiary amines, quaternary ammonium bases, quaternary ammonium salt compounds, nitrogen-containing heterocyclic compounds, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07D229/00C07D251/34C07F9/6584
Inventor 刘伟尚永华石滨王玉启孙立冬乔小飞黎源华卫琦
Owner WANHUA CHEM GRP CO LTD