Preparation method of epoxy group-containing phthalonitrile monomer

A technology of epoxy-based phthalonitrile and phenolic hydroxyl phthalonitrile, which is applied in the field of preparation of epoxy-containing phthalonitrile monomers, and can solve the limitations on the application and curing of phthalonitrile resins Poor toughness, high curing temperature and other problems, to achieve the effect of reducing production cost, lowering melting point, and simplifying the synthesis process

Active Publication Date: 2021-11-23
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the rigidity of the phthalonitrile monomer skeleton, it is easy to cause defects such as high monomer melting point, narrow processing window, high curing temperature, and poor toughness of the cured product during the processing of the phthalonitrile resin. The defects of phthalonitrile resin caused by the easy decomposition of curing agent at high temperature limit the application of phthalonitrile resin in various fields

Method used

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  • Preparation method of epoxy group-containing phthalonitrile monomer
  • Preparation method of epoxy group-containing phthalonitrile monomer
  • Preparation method of epoxy group-containing phthalonitrile monomer

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[0029] The invention provides a method for preparing epoxy-containing phthalonitrile monomers. The phenolic hydroxyl-containing phthalonitrile and epihalohydrin are used as raw materials and blended in alkaline solution under the catalysis of quaternary ammonium salts for reaction. to obtain a mixed solution containing epoxy-based phthalonitrile monomers, which is purified to obtain epoxy-containing phthalonitrile monomers,

[0030] Wherein the molecular structural formula of the phenolic hydroxyl-containing phthalonitrile is I or II,

[0031]

[0032] In said structural formula I, R 1 is hydroxyl or hydrogen, R 2 is hydroxyl or hydrogen, and there is one and only one hydroxyl in the structural formula I,

[0033] In the structural formula II, R is oxygen or sulfur.

[0034] The method of the present invention uses phenolic hydroxyl-containing phthalonitrile and epihalohydrin as raw materials to react quaternary ammonium salts under alkaline conditions, and obtains epoxy...

Embodiment 1

[0041] A kind of preparation method that low melting point contains epoxy group phthalonitrile monomer, comprises the following steps:

[0042] Step 1: In a three-necked flask, add 2.88g (0.02mol) of 4-hydroxyphthalonitrile, 92.52g (1mol) of epichlorohydrin, and 1.29g (0.004mol) of tetrabutylammonium bromide, and weigh the hydrogen Potassium oxide 5.61g (0.1mol) is made into the potassium hydroxide aqueous solution that mass fraction is 50% and is added in the there-necked flask, mechanically stirred at 10 ℃ for 48h to obtain the mixed solution of the phthalonitrile monomer containing epoxy group;

[0043] Step 2: Treatment of the mixed solution: pour out the reaction supernatant, remove excess epichlorohydrin by rotary evaporation, extract with dichloromethane, wash with saturated saline until the solution is neutral, add anhydrous calcium chloride and dry for 24 hours, Utilize rotary evaporation to remove dichloromethane to obtain the crude product of the phthalonitrile mono...

Embodiment 2

[0054] A kind of preparation method that low melting point contains epoxy group phthalonitrile monomer, comprises the following steps:

[0055] Step 1: In a three-necked flask, add 2.88g (0.02mol) of 3-hydroxyphthalonitrile and 54.79g (0.40mol) of epoxy bromide, 0.92g (0.006mol) of tetramethylammonium bromide, add di Chloromethane 94.0ml, take by weighing 3.20g (0.08mol) of sodium hydroxide and be made into the sodium hydroxide aqueous solution that mass fraction is 40% and join in the there-necked flask, mechanically stir 30h under 20 ℃ to obtain epoxy-containing phthalo A mixture of nitrile monomers;

[0056] Step 2: Treatment of the mixed solution: pour out the reaction supernatant and extract with dichloromethane; wash with saturated brine until the solution is neutral, add anhydrous calcium chloride to dry for 24 hours, and use rotary evaporation to remove dichloromethane and excess Epibromohydrin obtains the crude product of the phthalonitrile monomer containing epoxy g...

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Abstract

The invention discloses a preparation method of an epoxy group-containing phthalonitrile monomer, and relates to the technical field of organic synthesis. The method comprises the following steps: blending phenolic hydroxyl group-containing phthalonitrile and epoxy halopropane serving as raw materials in alkali liquor for a reaction under the catalysis of quaternary ammonium salt to obtain a mixed solution of an epoxy group-containing phthalonitrile monomer, and purifying the mixed solution to obtain the epoxy group-containing phthalonitrile monomer. According to the invention, the melting temperature of the phthalonitrile monomer is reduced, and the processing window of phthalonitrile is widened, so the application field of phthalonitrile resin is expanded.

Description

technical field [0001] The invention discloses a preparation method, relates to the technical field of organic synthesis, in particular to a preparation method of epoxy group-containing phthalonitrile monomer. Background technique [0002] Phthalonitrile resin is widely used because of its excellent high temperature resistance, high flame retardancy, high carbon residue rate, low water absorption, good mechanical properties and excellent high glass transition temperature, unique optical and electrical properties Used in coatings, adhesives, high temperature resistant material matrix resin and other fields. However, due to the rigidity of the phthalonitrile monomer skeleton, it is easy to cause defects such as high monomer melting point, narrow processing window, high curing temperature, and poor toughness of the cured product during the processing of the phthalonitrile resin. The defects of the phthalonitrile resin caused by the easy decomposition of the curing agent at hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/23C07D303/24C08G73/06
CPCC07D303/24C07D303/23C08G73/06
Inventor 杨志洲王彬张华栋
Owner QILU UNIV OF TECH
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