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A kind of cyclic biscarbodiimide compound and its preparation method

A biscarbodiimide and compound technology is applied in the field of novel cyclic biscarbodiimide compounds and their preparation, which can solve problems such as deterioration of operating environment, and achieve the effects of easy crystallization and purification, and convenient processing and operation.

Active Publication Date: 2019-04-02
SHANGHAI LANGYI FUNCTIONAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since both mono- and polycarbodiimide compounds are linear carbodiimide compounds, they generate volatile isocyanate compounds during use, emit bad odors, and have inherent defects that deteriorate the operating environment.

Method used

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  • A kind of cyclic biscarbodiimide compound and its preparation method
  • A kind of cyclic biscarbodiimide compound and its preparation method
  • A kind of cyclic biscarbodiimide compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]1) Add 12mL of concentrated sulfuric acid to 20mL of aqueous solution, heat to 80°C, slowly add 27g of 2-isopropylaniline (1), continue heating and stirring for 15 minutes, then spin evaporate to remove water. Argon atmosphere, heated to 260°C, and continued the reaction for 12h. After cooling down to room temperature, 200mL of 10% aqueous sodium hydroxide solution was added, heated to 90°C, reacted for 30 minutes, cooled and filtered. After the filtrate was adjusted to pH=1 with concentrated sulfuric acid, a large number of solids were precipitated, filtered to obtain 40g sulfoisopropylaniline (2); then in 500mL N,N-dimethylformamide solution, the resulting 40g product (2 ) and 7.2mL of liquid bromine (dissolved in 50mL of N,N-dimethylformamide solution) continued to react for 3.5 hours at room temperature to obtain 35g of brown-red solid bromosulfonic acid isopropylaniline (3); then 35g The product (3) and 300mL of 10% hydrochloric acid were added to a 500mL single-ne...

Embodiment 2

[0046] 1) Add 12mL of concentrated sulfuric acid into 20mL of aqueous solution, heat to 85°C, slowly add 26g of 2-methylaniline (1), continue heating and stirring for 15 minutes, and spin off the water. Argon atmosphere, heated to 250°C, continued the reaction for 13h. After cooling down to room temperature, 200mL of 10% aqueous sodium hydroxide solution was added, heated to 90°C, reacted for 30 minutes, cooled and filtered. After adjusting the filtrate to pH=1 with concentrated sulfuric acid, a large number of solids were precipitated, filtered to obtain 45g of sulfonic acid methylaniline (2); And 9.0mL liquid bromine (dissolved in 50mL N,N-dimethylformamide solution) continued to react at room temperature for 4 hours to obtain 40g brownish red solid bromosulfonic acid methylaniline (3); then 40g product ( 3) and 350mL of 11% hydrochloric acid were added to a 500mL single-necked bottle, heated to reflux for 11 hours, cooled to room temperature, neutralized with saturated sod...

Embodiment 3

[0052] 1) Add 12mL of concentrated sulfuric acid to 20mL of aqueous solution, heat to 80°C, slowly add 27g of 2-tert-butylaniline (1), continue heating and stirring for 15 minutes, then spin evaporate to remove water. Argon atmosphere, heated to 270°C, and continued to react for 12h. After cooling down to room temperature, 150 mL of 10% aqueous sodium hydroxide solution was added, heated to 90°C, reacted for 30 minutes, cooled, and filtered. After the filtrate was adjusted to pH=1 with concentrated sulfuric acid, a large number of solids were precipitated, filtered to obtain 54g sulfonic acid tert-butylaniline (2); then in 500mL N,N-dimethylformamide solution, the resulting 54g product (2 ) and 9.9mL liquid bromine (dissolved in 50mL N,N-dimethylformamide solution) continued to react for 4 hours at room temperature to obtain 52g brownish red solid bromosulfonic acid tert-butylaniline (3); then 52g The product (3) and 300mL of 10% hydrochloric acid were added to a 500mL single...

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Abstract

The invention relates to a novel cyclic bicarbodiimide compound (I) and a preparation method of the novel cyclic bicarbodiimide compound. Compared with monocarbodiimide, the novel cyclic bicarbodiimide compound has a higher molecular weight and a higher melting point; the disadvantage that the monocarbodiimide is easily transferred outward from compounds including polyester, polyurethane and like at high temperature is overcome; the anti-hydrolytic property of a material is improved; meanwhile, the defects that an existing bicarbodiimide compound is easily irregularly curled, easily forms a rubber state at room temperature and is not easy to crystallize and purify are overcome; the anti-hydrolytic effect is good and the bicarbodiimide compound has a good anti-hydrolytic property; the service life of a polyester material is improved; the bicarbodiimide compound can be used as an anti-hydrolytic stabilizer and is used for polyurethane and polyester elastomers, and especially can be used for photovoltaic industry, biodegradable materials and the like. The formula (I) is shown in the description.

Description

technical field [0001] The invention relates to a novel cyclic 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 m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D257/10C08K5/29C08L67/00C08L75/04
CPCC07D257/10C08K5/29C08L67/00C08L75/04
Inventor 唐晓峰颜晓晨董建廷刘宾
Owner SHANGHAI LANGYI FUNCTIONAL MATERIALS
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