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DOPO derivatives as well as preparation method and application thereof

A compound and heteroaryl technology, applied to a class of DOPO derivatives, their preparation and application fields, can solve the problems of early degradation of polymer materials, reduced thermal stability of flame retardants, and increased oxidation performance.

Active Publication Date: 2014-10-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The introduction of hydroxyl groups reduces the thermal stability of flame retardants, which is unfavorable to the processing of engineering plastics
The introduction of alkoxy group increases the oxidized performance, which will lead to the early degradation of polymer materials
[0009] One object of the present invention is to provide a kind of halogen-free flame retardant based on DOPO compound, this halogen-free flame retardant not only has good flame retardant effect, but also has very high thermal stability and chemical stability, can overcome existing DiDOPO Disadvantages of insufficient chemical resistance and strong plasticity

Method used

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  • DOPO derivatives as well as preparation method and application thereof
  • DOPO derivatives as well as preparation method and application thereof
  • DOPO derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Embodiment 1 has the preparation of formula (2) structure compound

[0082] DOPO (86.40 g, 0.40 mol), acetophenone (24.05 g, 0.20 mol) and 10 ml of xylene were added to a three-necked flask equipped with a thermometer, a water separator, a magnetic stir bar and a constant pressure funnel. Under nitrogen protection, the mixture was heated to 154°C, and phosphorus oxychloride was added dropwise. POCl 3 (30.25g) was slowly added dropwise to the reaction solution within 25 hours, and the distillate was collected in the water trap, keeping the reaction temperature at 154-160°C. After dropping phosphorus oxychloride, keep warm for half an hour. After cooling, add 120g of isopropanol, stir under reflux, most of the crude product dissolves after softening, and the system becomes turbid. Stirring was stopped, cooled, and a large amount of product precipitated after standing for a period of time. Suction filtration, the solid product was first washed with a small amount of is...

Embodiment 2

[0084] Embodiment 2 has the preparation of formula (3) structure compound

[0085] DOPO (86.40 g, 0.40 mol) and naphthalene ethyl ketone (34.04 g, 0.20 mol) were added into a three-necked flask equipped with a thermometer, a magnetic stir bar and a constant pressure funnel. Under nitrogen protection, the mixture was heated to 170°C, and phosphorus oxychloride was added dropwise. POCl 3 (15.96g) was slowly added dropwise in the reaction solution within 20 hours, keeping the reaction temperature at 170-180 degrees. After dropping phosphorus oxychloride, keep warm for half an hour. 31 P NMR spectrum showed no starting material. Cool, add 50ml of 90% ethanol to dissolve, then drop about 60ml of 2.5% Na 2 CO 3 Solution The pH of the reaction solution was adjusted to 6-7, and the white solid product was obtained by suction filtration after reflux for half an hour. Yield 70.6%.

[0086] The obtained product is characterized by H spectrum and P spectrum on a magnetic resonance ...

Embodiment 3

[0088] According to the preparation method in Example 1, phosphorus oxychloride was changed into 13.7 grams of phosphorus trichloride to obtain a compound having the structure of formula (2). Yield 75.8%.

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Abstract

The application relates to a compound capable of being used as a novel halogen-free flame retardant. The compound is prepared from aryl ketone and a DOPO compound in the presence of an acid catalyst. The compound has the advantages of good flame retardancy and good thermal stability and chemical stability.

Description

technical field [0001] The application relates to a halogen-free flame retardant and a preparation process thereof. Background technique [0002] Polymer materials are widely used in electronic appliances, automobiles, construction, textiles and other industries. However, due to the flammability of polymer materials, it is necessary to add flame retardants in actual use to meet the requirements of fire safety. Traditionally, brominated flame retardants are usually added to polymer materials to achieve flame retardant effects. However, when brominated flame retardants burn, they will produce strong irritating hydrogen bromide gas, thick smoke, and even some strong carcinogenic substances, which limits the use of brominated flame retardants. The European Union has formulated laws and regulations such as REACH and RoHS to restrict the use of certain brominated flame retardants, so the industry has begun to turn to halogen-free flame retardants. [0003] In terms of halogen-f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C08K5/5313C08L69/00B32B33/00B32B17/00
Inventor 姚强周浩张伟伟曹微虹刘正西徐子平
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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