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Flame-retardant monomer containing DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) groups and preparation method and application of flame-retardant monomer

A technology of flame retardant monomers and groups, which is applied in the field of flame retardant monomers containing DOPO groups and its preparation, achieving the effects of high yield, easy availability of raw materials, and increased flame retardant efficiency

Inactive Publication Date: 2014-04-30
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on DOPO-reactive flame-retardant monomers containing unsaturated double bonds and high flame-retardant efficiency.

Method used

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  • Flame-retardant monomer containing DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) groups and preparation method and application of flame-retardant monomer
  • Flame-retardant monomer containing DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) groups and preparation method and application of flame-retardant monomer
  • Flame-retardant monomer containing DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) groups and preparation method and application of flame-retardant monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Dissolve 2.16g (0.01mol) of DOPO in 10mL of dichloromethane, place in an ice-water bath, and add 2mL of carbon tetrachloride under stirring conditions. After 10 min, 2 mL of triethylamine was slowly added. After 1 min, 1.30 g (0.01 mol) of hydroxyethyl methacrylate was slowly added dropwise, and after the dropwise addition was completed, the temperature was raised to 20° C. and stirring was continued for 8 h to stop the reaction. Afterwards, it was filtered under reduced pressure to remove the triethylamine salt. The filtrate was transferred to a separatory funnel and washed several times with 3% NaOH solution, distilled water, and saturated NaCl aqueous solution. Anhydrous MgSO for organic layer 4 Without drying, filter, evaporate the solvent, and finally concentrate to obtain a yellow oil, which is analyzed by hydrogen spectrum (such as figure 1 ) and phosphorous spectra (such as figure 2 ) was confirmed as the target product flame retardant monomer containing DO...

Embodiment 2

[0031] Dissolve 2.16g (0.01mol) of DOPO in 10mL of tetrahydrofuran, place in an ice-water bath, and add 2mL of carbon tetrachloride under stirring conditions. After 10 min, 2 mL of pyridine was slowly added. After 1 min, 1.95 g (0.015 mol) of hydroxyethyl methacrylate was slowly added dropwise, and after the dropwise addition was completed, the temperature was raised to 30° C. and stirring was continued for 6 h to stop the reaction. Then vacuum filtration under reduced pressure to remove pyridinium salt. The filtrate was transferred to a separatory funnel and washed several times with 3% NaOH solution, distilled water, and saturated NaCl aqueous solution. Anhydrous MgSO for organic layer 4 Without drying, filter, evaporate the solvent, and finally concentrate to obtain a yellow oil, which is analyzed by hydrogen spectrum (such as figure 1 ) and phosphorous spectra (such as figure 2 ) was confirmed as the target product flame retardant monomer containing DOPO groups, and t...

Embodiment 3

[0033] Dissolve 2.16g (0.01mol) of DOPO in 10mL of toluene, place in an ice-water bath, and add 2mL of carbon tetrachloride under stirring conditions. After 10 min, 2 mL of triethylamine was slowly added. After 1 min, 2.60 g (0.02 mol) of hydroxyethyl methacrylate was slowly added dropwise, and after the dropwise addition was completed, the temperature was raised to 40° C. and stirring was continued for 4 h to stop the reaction. Afterwards, it was filtered under reduced pressure to remove the triethylamine salt. The filtrate was transferred to a separatory funnel and washed several times with 3% NaOH solution, distilled water, and saturated NaCl aqueous solution. Anhydrous MgSO for organic layer 4 Without drying, filter, evaporate the solvent, and finally concentrate to obtain a yellow oil, which is analyzed by hydrogen spectrum (such as figure 1 ) and phosphorous spectra (such as figure 2 ) was confirmed as the target product flame retardant monomer containing DOPO group...

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Abstract

The invention discloses a flame-retardant monomer containing DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) groups, and a preparation method and an application of the flame-retardant monomer, and relates to a compound. The method comprises the steps of sequentially adding an organic solvent, carbon tetrachloride and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide into a reaction flask, putting in an ice water bath, adding hydroxyethyl methylacrylate and an acid-binding agent while stirring, after temperature rise reaction, decompressing, and performing suction filtration to remove acid-binding agent salt, purifying a crude product through spin steaming, washing and dryness, and obtaining a product, namely the flame-retardant monomer containing the DOPO groups. The flame-retardant monomer containing the DOPO groups can be applied in preparing a flame-retardant high molecular material. A reaction condition is mild, the productivity is high, the product purification and separation are simple, and the extended production is easy. The monomer is introduced into a polymer matrix such as polystyrene and polymethyl methacrylate by a free radical copolymerization manner, an intrinsic flame-retardant polymer material is prepared, and the defects of poor compatibility of an additive flame retardant and the matrix, high loss possibility during use, poor water resistance and the like are overcome.

Description

technical field [0001] The invention relates to a compound, in particular to a DOPO group-containing flame retardant monomer and its preparation method and application. Background technique [0002] In today's society, polymer materials have been widely used in various fields of national life. Because of their flammability as polymer materials, flame retardant technology has attracted global attention. At present, the flame retardant method of polymer materials is widely used to add flame retardants in the process of polymer processing, commonly used are halogen, red phosphorus and Al(OH) 3 and other additive flame retardants. Most of the flame retardant modification of polyolefin materials uses this kind of flame retardant, but because it is usually added in a large amount, and it needs to be blended with the base material during construction, but because most of the polymer macromolecular chains are non-polar chains, adding The semi-crystalline characteristics of the upp...

Claims

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Application Information

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IPC IPC(8): C07F9/6574C08F220/14C08F230/02C08F212/08
Inventor 戴李宗陈国荣袁丛辉罗伟昂刘诚叶华立余世荣毛杰李聪何凯斌刘新瑜
Owner XIAMEN UNIV
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