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Method for producing carbodiimide compound

A technology of carbodiimide and compounds, which is applied in the field of preparation of carbodiimide compounds, can solve problems such as complicated procedures and achieve high yields

Pending Publication Date: 2020-10-30
NISSHINBO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to solve this problem, a known method is to distill off the catalyst under reduced pressure during or after the synthesis of the carbodiimide compound, but there is a problem that the process is complicated.

Method used

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  • Method for producing carbodiimide compound
  • Method for producing carbodiimide compound
  • Method for producing carbodiimide compound

Examples

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preparation example Construction

[0054] 1. The preparation method of carbodiimide compound

[0055] The preparation method of the carbodiimide compound of the present embodiment includes: adding an inorganic alkali metal compound (B) and a compound (D-1) selected from a phase transfer catalyst (C), the following general formula (2-1) and A carbodiimide production step of reacting an aliphatic tertiary isocyanate compound (A) in the presence of at least one compound (D-2) represented by the following general formula (2-2).

[0056] [chemical formula 4]

[0057]

[0058] (In formula (2-1), Z is methyl, ethyl, propyl, butyl or phenyl. R 2 It is an alkylene group having 2-3 carbon atoms. n is an integer of 2-500. )

[0059] [chemical formula 5]

[0060]

[0061] (In formula (2-2), R 3 It is an alkylene group having 2-3 carbon atoms. p is an integer of 2-500. )

[0062] As mentioned above, an inorganic alkali metal compound normally functions as a catalyst which accelerates the trimerization reactio...

Embodiment 1

[0240] 100 g of tetramethylxylylene diisocyanate as an aliphatic tertiary isocyanate compound (A), 0.5 g of potassium hydroxide (KOH) as an inorganic alkali metal (B) and 1.0 g of a phase transfer catalyst (C) 18-Crown-6-ether was added to a 300ml reaction vessel equipped with a reflux tube and a stirrer, stirred at 175°C under a nitrogen stream, and reacted until the NCO% measurement was 3.74%. The synthesis time was 5 hours.

[0241] In addition, the NCO% value of 3.74% refers to the case where 11 tetramethylxylylene diisocyanate undergoes decarboxylation condensation to produce a carbodiimide compound with a degree of polymerization of 10 (NCO groups at both ends). The content (mass %) of the NCO group in the carbodiimide compound below. With this value of 3.74% as the target value, the above reaction was carried out until the measured value of NCO% reached the target value.

[0242] As a result of analyzing the obtained isocyanate-terminated polytetramethylxylylenecarbod...

Embodiment 2

[0247] 100 g of 3-isopropenyl-α,α-dimethylbenzyl isocyanate as the aliphatic tertiary isocyanate compound (A), 0.5 g of potassium hydroxide (KOH) as the inorganic alkali metal (B) and 1.0 g as the phase The 18-crown-6-ether of transfer catalyst (C) is added in the 300ml reaction vessel that is equipped with reflux tube and stirrer, under nitrogen stream, stirs at 175 ℃, reacts until by infrared absorption (IR) spectrometry and wavelength 2200 -2300cm -1 The absorption of the isocyanate groups disappears (until the NCO% is 0%). The synthesis time was 20 hours.

[0248] The resulting bis(3-isopropenyl-α,α-dimethylbenzyl)monocarbodiimide was analyzed, and it was confirmed by infrared absorption (IR) spectroscopy that the wavelength was 2118cm -1 Around the absorption peak of the carbodiimide group. Absorption wavelength due to isocyanurate could not be confirmed, wavelength 1710cm -1 Left and right, wavelength 1411cm -1 The left and right absorption peaks, the absorption wav...

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Abstract

This method for producing a carbodiimide compound comprises a carbodiimide generation step in which an aliphatic tertiary isocyanate compound (A) is reacted in the presence of an inorganic alkali metal compound (B) and at least one among a phase-transfer catalyst (C), a compound (D-1) represented by general formula (2-1), and a compound (D-2) represented by general formula (2-2).

Description

technical field [0001] The invention relates to a method for preparing carbodiimide compounds, in particular to a method for preparing carbodiimide compounds from isocyanates. In addition, the present invention also relates to a preparation method of polyurethane, application of carbodiimide compound, carbodiimide composition, stabilizer and ester resin composition. Background technique [0002] Carbodiimide compounds are useful in various applications such as stabilizers for various resins such as thermoplastic resins and hydrolysis inhibitors. [0003] When producing carbodiimide compounds from isocyanates, it is known to use organophosphorus catalysts as carbodiimidization catalysts. [0004] For example, Patent Document 1 describes that polyisocyanate is reacted in the presence of a phosphorus-containing catalyst to form polyisocyanate carbodiimide. [0005] In addition, in Patent Document 2, examples of carbodiimide-forming catalysts include 1-phenyl-2-phosphole-1-oxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C267/00B01J23/04B01J31/06B01J31/26C07B61/00
CPCB01J31/06C07C267/00B01J31/26C07B61/00C08G18/025C08G18/225C08G18/168C08G18/163C08G18/765C08G18/8108C08G18/283C08G18/4833C08G18/095C08G18/10C08G18/42C08G18/797B01J23/04C07C2523/04C07C2531/02
Inventor 松本展幸柳沢健一
Owner NISSHINBO CHEM
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