Organic phosphaphenanthrene derivatives, and preparation method and application thereof

A technology of organophosphorus and derivatives, which is applied in the field of organophosphorus halogen-free flame retardants, can solve the problems of easy migration, poor flame retardant performance, high flame retardant dosage and high price, and achieve the expansion of application fields, improvement of flame retardant performance, Effect of improving flame retardancy

Active Publication Date: 2016-06-15
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, ordinary DOPO compounds have poor heat resistance and begin to decompose at about 200°C and complete at about 300°C, making it difficult to adapt to the processing conditions of most polymer materials.
On the other hand, due to the small molecular weight, strong volatility, and easy sublimation of ordinary DOPO compounds, they are easy to migrate in the polymer, which makes the flame retardancy of the material worse. Therefore, modifying DOPO compounds to increase their molecular weight can obtain Good flame retardant
However, the above-mentioned method of modifying DOPO has certain disadvantages
For example, grafting DOPO onto a polymer to prepare a polymer directly containing DOPO can greatly improve the flame retardant efficiency of the polymer, but its mechanical properties will be greatly reduced; a silane coupling agent molecule can only Reaction with a DOPO molecule, the hydrolysis of grafted DOPO is often affected by solubility; oligomeric silsesquioxane POSS is expensive and costly, and the price is high for the amount of flame retardant, etc.

Method used

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  • Organic phosphaphenanthrene derivatives, and preparation method and application thereof
  • Organic phosphaphenanthrene derivatives, and preparation method and application thereof
  • Organic phosphaphenanthrene derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1, preparation glycerol acrylate grafted DOPO

[0062] 1. Preparation of glycerol triacrylate

[0063] Get 25g of glycerol and 47.64 ml of acryloyl chloride, the molar ratio of the functional groups of hydroxyl and acid chloride is 1:1.2 at this time, mix glycerol and 300 ml of dichloromethane under the condition of ice-water bath, add 81.28 ml of Triethylamine was used as an acid-binding agent, and acryloyl chloride was added dropwise in an ice-water bath for half an hour, then warmed up to room temperature and stirred for 24 hours. The solution is light yellow, and there is a large amount of white insoluble powder at the same time.

[0064] The product of the reaction was filtered, and the light yellow filtrate was taken and evaporated by rotary evaporation to remove excess acryloyl chloride and triethylamine. The product was dissolved with 250 ml of dichloromethane, extracted with 80 ml of saturated aqueous sodium bicarbonate solution each time, for a tot...

Embodiment 2

[0070] Embodiment 2, preparation glycerol acrylate graft DOPO

[0071] 1. Glycerol chemically grafted acrylic acid

[0072] Take 25 grams of glycerol and 67.07 milliliters of acrylic acid. At this time, the functional group ratio of hydroxyl and carboxyl groups is 1:1.2. Mix glycerol and 300 milliliters of dichloromethane at room temperature, and add 3.32 grams of 4-dimethyl Aminopyridine was used as a catalyst, 185 g of N,N-dicyclohexylcarbodiimide was added as a dehydrating agent, acrylic acid was added dropwise to the glycerin solution, and the reaction was stirred at room temperature for 24 hours. The solution is light yellow, and there is a large amount of white insoluble powder at the same time.

[0073] The reaction product was filtered, and the light yellow filtrate was taken, which was rotary evaporated to remove excess acrylic acid. The product is dissolved with 250 milliliters of dichloromethane, extracted three to four times with 80 milliliters of 5% hydrochloric...

Embodiment 3

[0077] Embodiment 3, preparation glycerol acrylate grafted DOPO

[0078] 1. Preparation of glycerol triacrylate

[0079] Using the same method as in Example 2, except that the temperature is raised to 80-120° C., the catalyst becomes 15.51 grams of monohydrate toluenesulfonic acid, and 1 gram of cuprous chloride is added as a polymerization inhibitor at the same time, and the propylene oxide is still obtained. Triol Triacrylate.

[0080] 2. Glycerol acrylate grafted DOPO

[0081] Using the same method as in Example 1, a glycerol triacrylate derivative grafted with DOPO was also obtained by proton nuclear magnetic resonance spectroscopy.

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Abstract

The invention discloses organic phosphaphenanthrene derivatives, and a preparation method and application thereof. The structural formula of the organic phosphaphenanthrene derivatives is disclosed as Formula I, wherein the group disclosed as Formula II is from carboxylic acid derivatives or acyl chloride derivatives, the group A is from organic phosphaphenanthrene compounds, and the group A is connected with the group disclosed as Formula II through a P-C bond. The preparation method of the organic phosphaphenanthrene derivatives comprises the following steps: carrying out esterification reaction on glycerol and carboxylic acid derivatives or acyl chloride derivatives to obtain glycerol ester derivatives; and under the action of a catalyst, carrying out reaction on the glycerol ester derivatives and organic phosphaphenanthrene compounds. The organic phosphaphenanthrene derivatives can enhance the flame retardancy of the polymer, and can enhance the flame retardancy of the prepared material when being added as a functional aid for preparing high-polarity engineering plastics of PET (polyethylene terephthalate), PBT (polybutylene terephthalate) and other polyesters and PA6 (polyamide 6), PA66 (polyamide 66) and other polyamides.

Description

technical field [0001] The invention relates to an organophosphorus phenanthrene derivative and its preparation method and application, belonging to the field of organophosphorus halogen-free flame retardants. Background technique [0002] Since the birth of polymers, they have been widely used in people's lives due to their easy design and processing characteristics, but the Achilles heel of polymer materials - flammability, has brought serious problems to people's production and life safety. hazards. Shocking incidents such as the high-rise residential fire in Jing'an District, Shanghai, and the fire in the CCTV building were all caused by the poor flame retardancy of the polymer materials used. Most of the flame retardants used in traditional flame retardant materials are compounds rich in halogen components, but these compounds will release a large amount of harmful substances while being flame retardant, which seriously affects life safety. Therefore, research on new h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C08L67/02C08L77/02C08L77/06C08K5/5313
CPCC07F9/657172C08K5/5313C08L2201/02C08L67/02C08L77/02C08L77/06
Inventor 解明晨阳明书张世民丁艳芬王峰刘鹏
Owner INST OF CHEM CHINESE ACAD OF SCI
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