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Phosphaphenanthrene flame-retardant compound containing s-triazine structure, and preparation and use thereof

A technology of oxaphosphine and phenanthrene compounds, which is applied in the field of phosphorus-nitrogen synergistic flame retardant compounds, can solve the problem that the processing temperature of polymer materials cannot be met, the cost is unacceptable, and the synthesis and application of oxaphosphine phenanthrene compounds have not been seen Reporting and other issues, to achieve the effect of low cost, easy operation, and easy industrial production

Active Publication Date: 2009-03-04
SICHUAN DONGFANG INSULATING MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are certain problems in the direct use of DOPO monomer in the flame retardant of polymer materials: on the one hand, when DOPO is directly applied as a flame retardant to achieve the UL-94 V-0 flame retardant effect, the cost is unacceptable; on the other hand, due to DOPO begins to decompose at 180°C, which cannot meet the processing temperature of most polymer materials
Triazine flame retardants and oxaphosphaphenanthrene flame retardants have their own advantages, but so far, in terms of phosphorus and nitrogen synergistic flame retardancy, there is no synthesis and analysis of oxaphosphine flame retardant compounds containing triazine structures. application report

Method used

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  • Phosphaphenanthrene flame-retardant compound containing s-triazine structure, and preparation and use thereof
  • Phosphaphenanthrene flame-retardant compound containing s-triazine structure, and preparation and use thereof
  • Phosphaphenanthrene flame-retardant compound containing s-triazine structure, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Compound 2,4,6-tris(4-(10-methinehydroxy-9,10-dihydro-9-oxa-10-phosphinanthrene-10-oxide)phenoxy)-1,3, The preparation method of 5-triazine, the steps are:

[0035] Add 21.6g (0.1mol) 9,10-dihydro-9-oxa-10-phosphinephenanthrene-10-oxide (DOPO) in a 500mL four-necked flask equipped with a stirrer, a thermometer, and a condenser tube, 13.4g (0.11mol) p-Hydroxybenzaldehyde, 200mL toluene solvent, start stirring and heating, and react at reflux temperature for 5h, cool to room temperature, filter, the solid matter obtained is washed with toluene, then with 2 parts of toluene and 1 part of methanol (volume ratio) mixed solvent to recrystallize the obtained solid to obtain a pure white crystalline intermediate with a yield of 93% and a melting point of 244-247°C.

[0036] Add 7.4g (0.040mol) cyanuric chloride, 40.66g (0.120mol) phosphorus-containing intermediate, 0.084g (0.0004mol) four-necked flask in the 500mL four-neck flask equipped with stirrer, thermometer, condenser a...

Embodiment 2

[0038] The amount of phosphorus-containing intermediate is increased to 43.26g (0.128mol), and sodium hydroxide is increased to 5.12g (0.128mol), and others are the same as in Example 1, to obtain product 40.9g, yield 93.8%.

Embodiment 3

[0040] The phase-transfer catalyst tetraethylammonium bromide is increased to 0.84g (0.004mol), and others are the same as in Example 1, to obtain 41.55g of the product, with a yield of 95.3%.

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Abstract

The invention discloses an oxa-phosphaphenanthrene flame retardant compound containing the sym-triazine structure and a preparation method thereof. The method is characterized in that an intermediate is synthesized from 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide(DOPO) and p-hydroxybenzaldehyde as raw material by the solution method, and then reacts with cyanuric chloride in the presence of phase transfer catalyst to obtain a 2,4,6-tri(4-(10-methenyl hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide)phenoxy)-1,3,5-triazine product. The compound is white crystal, and has a melting point of 166 to 169 DEG C, good thermal stability and high flame retardation efficiency, and can be adopted as a reactive flame retardant for the flame retardation of thermosetting resins such as epoxy resin, polyurethane and the like, and also as an additive flame retardant for the flame retardation of engineering plastics such as ABS, nylon and the like.

Description

technical field [0001] The invention belongs to the technical field of phosphorus-nitrogen synergistic flame-retardant compounds, and relates to a oxaphosphine flame-retardant compound containing a s-triazine structure 2,4,6-tris(4-(10-methinehydroxy-9,10 -dihydro-9-oxa-10-phosphophenanthrene-10-oxide)phenoxy)-1,3,5-triazine and its preparation method and application, the prepared compound can be used as a reactive flame retardant It can be used as an additive to prepare halogen-free flame retardant resin, and can be used as an additive flame retardant for halogen-free flame retardant of engineering plastics. Background technique [0002] Traditional halogenated flame retardants are widely used due to their high flame retardant efficiency, wide application range, no excessive deterioration of the physical and mechanical properties of the substrate, and obvious cost-effective advantages, and they occupy a dominant position in the flame retardant field. However, most halogen-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6571C09K21/12C08K5/5313C08L63/00C08L75/04C08L55/02C08L77/00
Inventor 唐安斌汤俊杰黄杰
Owner SICHUAN DONGFANG INSULATING MATERIAL
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