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Phosphorus-containing flame retardant with amino group as well as preparation method and application of flame retardant

A flame retardant and amine-based technology, which is applied in the field of phosphorus-containing flame retardants and their preparation, can solve the problems of inability to achieve environmentally friendly flame retardants, pollute the environment, and fail to achieve safety and environmental protection.

Pending Publication Date: 2021-03-05
GUANGDONG GUANGSHAN NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although the additive-type phosphorus-nitrogen halogen-free flame-retardant material has flame-retardant characteristics, it cannot be truly safe and environmentally friendly. Due to its migration and precipitation during production, storage, use, and scrapping, and most of the additives For reasons such as the easy hydrolysis of type flame retardants, its molecules or decomposition products or water-soluble substances will enter the environment, pollute the environment, and cannot be truly environmentally friendly flame retardants.

Method used

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  • Phosphorus-containing flame retardant with amino group as well as preparation method and application of flame retardant
  • Phosphorus-containing flame retardant with amino group as well as preparation method and application of flame retardant
  • Phosphorus-containing flame retardant with amino group as well as preparation method and application of flame retardant

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0077] A phosphorus-containing flame retardant with an amine group, the structure is as follows:

[0078]

[0079] The preparation method is as follows:

[0080] In a three-necked flask equipped with magnetic stirring and a thermometer, add 1 mol of diethylenetriamine and 2 mol of dimethyl hydroxymethyl phosphite, 200 mL of ethanol and 0.1 mol of sodium hydroxide, 0.1 g of DMAP, heat up to ethanol reflux, and react for 12 hours. Then add hydrochloric acid until the pH is 7, filter and wash to remove impurities, and obtain the phosphorus-containing flame retardant with the above structure.

[0081] 1 H NMR (400MHz, DMSO-d6): δ=3.49-3.51(d,12H,-P-O-CH 3 ),3.03-3.06(s,4H,-P-C H 2 -),2.66-2.69(t,8H,-NH-C H 2 -C H 2 -NH-),2.11-2.14(s,3H,-NH-).

preparation example 2

[0083] A phosphorus-containing flame retardant with an amine group, the structure is as follows:

[0084]

[0085] The preparation method is as follows:

[0086] Add 1 mol of diethylenetriamine and 1 mol of dimethyl hydroxymethyl phosphite, 200 mL of ethanol, 0.1 mol of sodium hydroxide, and 0.1 g of DMAP into a three-necked flask equipped with magnetic stirring and a thermometer, heat up to ethanol reflux, and react for 12 hours. Then add hydrochloric acid until the pH is 7, filter and wash to remove impurities, and obtain the phosphorus-containing flame retardant with the above structure.

[0087] 1 H NMR (400MHz, DMSO-d6): δ=5.00-5.03(s, 2H, -N H 2 ),3.48-3.50(d,6H,-P-O-CH 3 ),3.03-3.06(s,2H,-P-C H 2 -),2.85-2.88(t,2H,-NH-CH 2 -C H 2 -NH 2 ),2.65-2.68(t,2H,-NH-C H 2 -CH 2 -NH 2 ),2.51-2.55(s,4H,-NH-C H 2 -C H 2 -NH-).

preparation example 3

[0089] A phosphorus-containing flame retardant with an amine group, the structure is as follows:

[0090]

[0091] The preparation method is as follows:

[0092] (1) Under a nitrogen atmosphere, put 200mL glacial acetic acid, 0.5mol dimethyl phosphite and 0.5mol maleic acid into a three-port 500mL glass reactor with a stirring device and stir. At a stirring temperature of 60°C, 0.5mmol The Pb catalyst was dissolved in 20mL of glacial acetic acid, then added dropwise to the reaction system, reacted for 12h, and then separated the product;

[0093] 1 H NMR (400MHz, DMSO-d6) δ = 13.52-13.54 (s, 1H, -CH-CO-O H ),12.98-13.00(s,1H,-CH 2 -CO-O H ),3.47-3.49(d,6H,-P-O-C H 3 ),2.85-2.90(t,1H,-CH-),2.78-2.81(d,2H,-C H 2 -).

[0094] (2) Mix 1 mol of the product obtained in step (1), 2 mol of thionyl chloride and 200 mL of chloroform, react at reflux temperature, then add 1 mol of ethylenediamine and 0.1 mol of triethylamine to react for 30 minutes to obtain product B;

[00...

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Abstract

The invention provides a phosphorus-containing flame retardant with an amino group as well as a preparation method and application of the flame retardant. The phosphorus-containing flame retardant with the amino group has a structure as shown in a formula I. The phosphorus-containing flame retardant with the amino group provided by the invention can participate in polymerization reaction, and finally the phosphorus-containing group exists in a reaction system in the form of a chemical bond, so that the phosphorus-containing flame retardant with the amino group provided by the invention has excellent flame retardant property and can realize permanent flame retardance.

Description

technical field [0001] The invention belongs to the technical field of flame retardants, and relates to a phosphorus-containing flame retardant with amine groups, a preparation method and application thereof. Background technique [0002] At present, the domestic organic flame retardant market is mainly halogen and phosphorus. Halogen flame retardants generate more smoke and release irritating and corrosive gases during combustion, polluting the environment and endangering human health; Banned the use of halogenated flame retardants. Phosphorus-based flame retardants have the functions of flame retardancy, heat insulation, and oxygen insulation, and produce less smoke, are not easy to generate harmful gases, and have relatively little pollution to the environment. [0003] Phosphazene flame retardant is a phosphorus-containing flame retardant with excellent flame retardant effect. It has excellent flame retardant performance due to its high content of N and P elements. Pho...

Claims

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Application Information

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IPC IPC(8): C07F9/40C08G59/50C08G59/54C08G59/56C08G18/66C08G18/48C08G18/32
CPCC07F9/4009C07F9/4075C08G59/504C08G59/54C08G59/56C08G18/6685C08G18/4854C08G18/3206C08G18/3889
Inventor 潘庆崇
Owner GUANGDONG GUANGSHAN NEW MATERIALS CO LTD
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