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DOPO-phthalimide derivative, and preparation method and application thereof

A technology of phthalimide and derivatives is applied in the field of flame retardant modification of polymer materials to achieve the effects of high rigidity, low tension and satisfying processing conditions

Active Publication Date: 2018-10-12
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the present invention provides a brand-new idea for synthesizing organophosphorus / nitrogen flame retardants, which breaks through the limitations of conventional synthesis methods and solves the problem that phthalimide with extremely poor alkalinity cannot be synthesized by conventional methods. Problems with Diformamide Derivatives

Method used

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  • DOPO-phthalimide derivative, and preparation method and application thereof
  • DOPO-phthalimide derivative, and preparation method and application thereof
  • DOPO-phthalimide derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] There is the preparation of formula (I-i) structure compound

[0077] (1) DOPO (162.00 g, 0.75 mol) and 200 ml of xylene were added to a three-necked flask equipped with a thermometer, a magnetic stir bar, and a spherical condenser. Under the protection of nitrogen, the temperature of the system was slowly raised to 95°C. After the system was completely transparent, 22.50 g of paraformaldehyde was added in batches within 3 hours. After feeding, the temperature was continued to stir and react for 6 hours. Suction filtration while hot, the obtained solid was dried under vacuum at 80° C. for 8 hours to obtain 179 g of product with a yield of 97.0%.

[0078] (2) Weigh 116.03 g (0.47 mol) of the adduct of DOPO and paraformaldehyde, and add 300 ml of pyridine into a three-neck flask equipped with a thermometer and a magnetic stir bar. Then 180.10 g (0.94 mol) of p-toluenesulfonyl chloride were added slowly over 1 hour. Stir overnight at 25°C. Suction filtration, washin...

Embodiment 2

[0083] There is the preparation of formula (I-i) structure compound

[0084] (1) DOPO (162.00 g, 0.75 mol) and 200 ml of benzene were added to a three-necked flask equipped with a thermometer, a magnetic stir bar, and a spherical condenser. Under the protection of nitrogen, the temperature of the system was slowly raised to 70°C. 27 g of paraformaldehyde were added in portions over 4 hours. After feeding was completed, the stirring reaction was continued for 8 hours at this temperature. Suction filtration while hot, the obtained solid was dried under vacuum at 80° C. for 8 hours to obtain 181 g of product with a yield of 98.0%.

[0085](2) Weigh 116.03 g (0.47 mol) of the above-mentioned DOPO-alcohol compound, and add 300 ml of picoline into a three-necked flask equipped with a thermometer and a magnetic stir bar. Under the condition of ice bath, 114.90 g (0.60 mol) p-toluenesulfonyl chloride was slowly added. After feeding, the temperature of the reaction system will ri...

Embodiment 3

[0088] There is the preparation of formula (I-i) structure compound

[0089] (1) DOPO (162.00 g, 0.75 mol) and 200 ml of cyclohexane were added to a three-necked flask equipped with a thermometer, a magnetic stir bar, and a spherical condenser. Under the protection of nitrogen, the temperature of the system was slowly raised to 70°C. 24.75 grams of paraformaldehyde were added in portions over 4 hours. After the feeding was completed, the stirring reaction was continued for 15 hours at this temperature. Suction filtration while hot, the obtained solid was dried under vacuum at 80° C. for 8 hours to obtain 175 g of product with a yield of 95.0%.

[0090] (2) Weigh 116.03 g (0.47 mol) of the adduct of DOPO and paraformaldehyde, add 200 ml of pyridine and 100 ml of triethylamine into a three-necked flask equipped with a thermometer and a magnetic stir bar. Then 180.10 g (0.94 mol) of p-toluenesulfonyl chloride were added slowly over 1 hour. Stir overnight at 25°C. Suction f...

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Abstract

The invention provides a DOPO-phthalimide derivative with a structure as shown in a formula I which is described in the specification. The invention also provides a preparation method for the DOPO-phthalimide derivative. The preparation method comprises the following steps: 1) subjecting a DOPO derivative and an aldehyde compound to a nucleophilic addition reaction to prepare a DOPO-alcohol compound; (2) reacting the DOPO-alcohol compound with sulfonyl chloride so as to prepare a DOPO-sulfonate compound; and (3) subjecting the DOPO-sulfonate compound and a phthalimide metal salt to a nucleophilic substitution reaction so as to obtain the DOPO-phthalimide derivative. The invention further provides the application of the above DOPO-o-phthalimide derivative as a flame retardant to modification of polymer resin. The polymer resin having undergone flame-retardant modification passes the V-0 level in a vertical burning test; at the same time, a flame-retardant product is allowed to maintaingood thermal properties, mechanical properties and physical appearance.

Description

technical field [0001] The invention belongs to the technical field of flame-retardant modification of polymer materials, and specifically relates to a DOPO-phthalimide derivative, a preparation method and an application. Background technique [0002] Polymer materials are widely used in construction, transportation, electronic appliances and other fields. However, this material is highly flammable, so it must be modified before use to achieve the specified flame retardant rating. Brominated flame retardants have been widely used due to their advantages of high efficiency, low cost, and little impact on material properties. However, flame retardant products containing chlorine and bromine will produce strong irritating hydrogen halide gas, toxic smoke and even some strong carcinogenic substances during combustion. With the improvement of people's awareness of environmental protection, the promulgation and improvement of relevant laws, the use of brominated flame retardants...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C08K5/5313C08L67/04C08G59/50C08L77/06
CPCC07F9/657172C08G59/5033C08K5/5313C08L2201/02C08L67/04C08L77/06
Inventor 姚强刘川川
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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