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Novel bi-carbodiimide compound and preparation method thereof

A biscarbodiimide compound technology, applied in the field of new biscarbodiimide compounds and their preparation, can solve problems such as inconvenient use, increased operating burden, and difficult crystallization and purification, and achieve easy crystallization and purification, and improve Anti-hydrolysis performance, the effect of convenient processing operation

Active Publication Date: 2013-12-25
SHANGHAI LANGYI FUNCTIONAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the structural feature of this biscarbodiimide compound is that two symmetrical carbodiimides are connected by a methylene group. However, due to the flexibility of the methylene molecular chain segment, it is easy to be in a random coil shape. A variety of conformations are formed at room temperature, making this biscarbodiimide compound easy to form a rubber state at room temperature. Although its melting point is relatively high, the disadvantage of the rubber state at room temperature is that it is not easy to crystallize and purify, and it is inconvenient to use
Increased the burden of various operations, which is not conducive to processing and use

Method used

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  • Novel bi-carbodiimide compound and preparation method thereof
  • Novel bi-carbodiimide compound and preparation method thereof
  • Novel bi-carbodiimide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 3.54kg3,3',5,5'-tetraisopropylbiphenyldiamine and 5.22kg2,4,6-triisopropylphenyl isothiocyanate into the reactor, then inject 40L of toluene, Stir mechanically and mix evenly, then heat up to 90°C for addition reaction, keep warm for 8 hours until it is completely converted into dithiourea intermediate; add 4kg of 30%wt sodium hydroxide aqueous solution, and add 59.6kg of 10% sodium hydroxide dropwise within 2h under stirring at 30°C wt sodium hypochlorite aqueous solution, control the rate of addition so that the temperature does not rush to 60°C, react at 40°C for 3 hours after the drop is complete, and end the reaction. Washing, suction filtration removes impurity, filtrate layering, leaves and takes organic layer, obtains crude product after decompression distillation reclaims organic solvent, and crude product recrystallizes with 40L methanol, obtains 7.3kg white crystal biscarbodiimide compound (I -1),

[0033] Yield 90.57%;

Embodiment 2

[0035] Add 3.54kg3,3',5,5'-tetraisopropylbiphenyldiamine and 6.06kg2,4,6-tri-tert-butylphenyl isothiocyanate into the reactor, then inject 45L of toluene, Stir mechanically and mix evenly, then heat up to 90°C for addition reaction, keep warm for 10 hours until it is completely converted into dithiourea intermediate; add 4kg of 30%wt sodium hydroxide aqueous solution, and add 52.8kg of 10% sodium hydroxide dropwise within 2h under stirring at 30°C wt sodium hypochlorite aqueous solution, control the rate of addition so that the temperature does not rush to 60°C, react at 40°C for 4 hours after the drop is complete, and end the reaction. Washing, suction filtration to remove impurities, filtrate layering, leave the organic layer, obtain the crude product after decompression distillation reclaims the organic solvent, the crude product is recrystallized with 45L methanol, obtains 7.9kg white crystal biscarbodiimide compound (I -2), yield 88.76%;

Embodiment 3

[0037] Add 2.4kg3,3',5,5'-tetramethylbenzidinediamine and 5.22kg2,4,6-triisopropylphenyl isothiocyanate into the reaction kettle, then inject 30L dichloroethylene Alkanes, mechanically stirred and mixed evenly, then heated up to 70°C for addition reaction, kept the temperature for 3 hours until it was completely converted into dithiourea intermediate; added 3.5kg of 30%wt sodium carbonate aqueous solution, stirred at 30°C, and added dropwise 45.3 kg10%wt sodium hypochlorite aqueous solution, control the rate of addition so that the temperature does not rush to 50°C, react at 40°C for 3h after the drop is complete, and end the reaction. Wash with water, remove impurity by suction filtration, filtrate layering, keep organic layer, obtain crude product after vacuum distillation reclaims organic solvent, crude product recrystallizes with 30L methanol, obtains 6.2kg white crystal biscarbodiimide compound (I -3), yield 89.33%;

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Abstract

The invention relates to a novel bi-carbodiimide compound and a preparation method thereof. The preparation method comprises the steps of: carrying out addition reaction on 3,3',5,5'-tetra-alkyl benzidine and aryl isothiocyanate at a certain temperature in an organic solvent, preparing a dithiobiurea intermediate within 6-10h, adding 30wt% alkaline solution into the suspension solution, stirring at 30 DEG C, dropwise adding 10wt% oxidizing agent water solution within 2-3h, controlling the dropwise adding temperature to be not higher than 50 DEG C, stirring and reacting for 3-4h at 40 DEG C after the oxidizing agent water solution is completely added dropwise, washing by using water, carrying out suction filtering, removing impurity, layering the filtrate, remaining an organic layer, distilling under reduced pressure, recovering organic solvent to obtain a crude product, re-crystallizing the crude product by using methanol, drying, so as to obtain white crystals bi-carbodiimide compound. As an anti-bydrolysis stabilizing agent, the bi-carbodiimide compound is manly added in polyurethane and polyester elastomers.

Description

technical field [0001] The invention relates to a novel biscarbodiimide compound and a preparation method thereof, which can be used as an anti-hydrolysis stabilizer for polyurethane and polyester elastomers, especially for photovoltaic industry, biodegradable materials and the like. Background technique [0002] Carbodiimide compounds are excellent anti-hydrolysis stabilizers. When polymer materials containing ester groups are attacked by water or acid, the ester bond in the molecule is cleaved into alcohol and acid, and the acid will increase the hydrolysis rate exponentially. , carbodiimide compounds can capture this free carboxylic acid, and quickly react at room temperature to form a stable ureide, preventing further hydrolysis, thereby improving the hydrolytic stability of polymer materials. [0003] Carbodiimide compounds include monocarbodiimide, polycarbodiimide, and polycarbodiimide compounds. Domestic research on carbodiimides started relatively late, and market p...

Claims

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Application Information

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IPC IPC(8): C07C267/00
Inventor 杨源源唐晓峰
Owner SHANGHAI LANGYI FUNCTIONAL MATERIALS
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