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9,10-dihydro-9-oxa-10-phosphenanthrene-10-oxide (DOPO) group phosphorus-nitrogen flame retardant and preparation method and application thereof

A technology of nitrogen-phosphorus flame retardants and flame retardants, applied in chemical instruments and methods, organic chemistry, compounds of Group 5/15 elements of the periodic table, etc., can solve the problem of affecting the mechanical properties of cured resins and reduce the vitrification of cured resins Transformation temperature, can not meet the processing temperature and other problems, to achieve the effect of environmental protection, material comprehensive performance improvement, easy to control

Inactive Publication Date: 2013-04-24
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are certain deficiencies in the direct use of DOPO monomers in the flame retardancy of polymers. On the one hand, because DOPO begins to decompose at 180 ° C, it cannot meet the processing temperature of some polymers above 200 ° C, so its thermal stability should be improved; On the one hand, when DOPO is directly used as a flame retardant in epoxy resin, oxazine resin and unsaturated resin, since the molecule contains only one active hydrogen, it will reduce the glass transition temperature of the cured resin and affect the mechanical properties of the cured resin.

Method used

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  • 9,10-dihydro-9-oxa-10-phosphenanthrene-10-oxide (DOPO) group phosphorus-nitrogen flame retardant and preparation method and application thereof
  • 9,10-dihydro-9-oxa-10-phosphenanthrene-10-oxide (DOPO) group phosphorus-nitrogen flame retardant and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Nitrogen phosphorus flame retardant ( 1 ) The synthetic steps are as follows:

[0027] In a three-necked flask equipped with a stirrer and a reflux condenser, add 18.4g 4,4'-diaminobiphenyl, 21.2g benzaldehyde, and 400g ethanol, stir, control the reaction temperature at 50°C, and cool down after 4 hours of reaction , and then the reaction mixture was filtered, washed, and dried in an oven at 80° C. for 6 h to obtain a yellow imine intermediate with a yield of 93%.

[0028] Add 18.0g of imine, 21.6g of DOPO, and 400g of ethanol obtained above into a three-necked flask equipped with a stirrer and a reflux condenser, stir and control the reaction temperature at 50°C, react for 10 hours, cool down, and then filter the product , washed, and dried in an oven at 80°C for 8 hours to obtain a pale yellow solid nitrogen-phosphorus flame retardant ( 1 ), yield 94%.

[0029] The resulting product nitrogen phosphorus flame retardant ( 1 ) carried out infrared spectroscopy, NMR, ...

Embodiment 2

[0037] Nitrogen phosphorus flame retardant ( 2 ) The synthetic steps are as follows:

[0038] Add 18.4g of 4,4'-diaminobiphenyl, 24.4g of p-hydroxybenzaldehyde, and 400g of ethanol into a three-necked flask equipped with a stirrer and a reflux condenser, stir, and control the reaction temperature at 50°C. After 4 hours of reaction After cooling, the reaction mixture was filtered, washed, and dried in an oven at 80°C for 6 hours to obtain a brown imine intermediate with a yield of 93%.

[0039]Add 19.6g of imine, 21.6g of DOPO, and 400g of ethanol obtained above into a three-necked flask equipped with a stirrer and a reflux condenser, stir and control the reaction temperature at 50°C, react for 10 hours, cool down, and then filter the product , washed, and dried in an oven at 80°C for 8 hours to obtain a beige solid nitrogen-phosphorus flame retardant ( 2 ), yield 91%.

[0040] The resulting product nitrogen phosphorus flame retardant ( 2 ) carried out infrared spectroscopy...

Embodiment 3

[0048] Nitrogen phosphorus flame retardant ( 3 ) The synthetic steps are as follows:

[0049] Add 18.4g of 4,4'-diaminobiphenyl, 24.4g of salicylaldehyde, and 400g of ethanol into a three-necked flask equipped with a stirrer and a reflux condenser, stir, control the reaction temperature at 50°C, and cool down after 4 hours of reaction. Then the reaction mixture was filtered, washed, and dried in an oven at 80°C for 6 h to obtain a yellow imine intermediate with a yield of 91%.

[0050] Add 19.6g of imine, 21.6g of DOPO, and 400g of ethanol obtained above into a three-necked flask equipped with a stirrer and a reflux condenser, stir and control the reaction temperature at 50°C, react for 10 h and then cool, then filter the product. Washed and dried in an oven at 80°C for 8 h, the obtained light yellow solid nitrogen-phosphorus flame retardant ( 3 ), yield 93%.

[0051] Gained nitrogen phosphorus flame retardant ( 3 ) carried out infrared spectroscopy, NMR, mass spectrometry...

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Abstract

The invention relates to a 9,10-dihydro-9-oxa-10-phosphenanthrene-10-oxide (DOPO) group phosphorus-nitrogen flame retardant and a preparation method of the DOPO group phosphorus-nitrogen flame retardant. According to the preparation method, 4,4'-diaminodiphenyl and aromatic aldehyde undergo condensation reaction to obtain an imine intermediate product, and the imine intermediate product and DOPO undergo addition reaction to obtain the solid flame retardant. The preparation method is easy to control, good in repeatability, high in yield and suitable for large-scale production. The molecule of the flame retardant contains two flame retarding elements including phosphorus and nitrogen, and thus the flame retardant has good flame retarding effect and coal forming performance. Due to the fact that the molecules of the flame retardant have reactive hydrogen atoms of different numbers, the flame retardant can further react with resin with reactivity to obtain flame retarding resin. When the flame retarding resin is added to a polymer, the flame retarding property and the oxygen index of the polymer can be promoted, and the flame retarding level can reach Underwriters Laboratories (UL) 94V0.

Description

technical field [0001] The invention belongs to the technical field of phosphorus-containing flame-retardant materials, and in particular relates to a phosphorus-nitrogen flame retardant containing DOPO groups and a preparation method thereof. The flame retardant can be added to polymers in various ways and has excellent flame-retardant properties. Background technique [0002] Halogen-free flame retardant has become a key technology in the field of polymer material flame retardant research. Phosphorus and nitrogen based flame retardants have attracted widespread attention due to their advantages such as halogen-free, low toxicity, environmental protection, and high-efficiency flame retardant effects. 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO for short) and its derivatives, represented by oxaphosphinephenanthrene compounds, have good thermal stability, low volatility, and hydrolysis resistance. Good compatibility with polymers, not easy to precipitate, high-ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/5313C07F9/6574C08L63/00
Inventor 姚有为孙德朝
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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