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Hetero-naphthalene biphenyl bisphenol monomer and preparation method thereof, hetero-naphthalene biphenyl epoxy monomer and preparation method and application thereof, and flame-retardant epoxy resin

A technology of naphthalene biphenyl bisphenol and epoxy resin, applied in the field of bisphenol monomer, can solve problems such as poor solubility, and achieve the effects of simple post-processing, mild reaction conditions and high product purity

Active Publication Date: 2020-09-25
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, polyaryletherketone materials are semi-crystalline polymers with excellent chemical stability and mechanical properties, but their solubility is poor, and they are only soluble in concentrated sulfuric acid at room temperature.

Method used

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  • Hetero-naphthalene biphenyl bisphenol monomer and preparation method thereof, hetero-naphthalene biphenyl epoxy monomer and preparation method and application thereof, and flame-retardant epoxy resin
  • Hetero-naphthalene biphenyl bisphenol monomer and preparation method thereof, hetero-naphthalene biphenyl epoxy monomer and preparation method and application thereof, and flame-retardant epoxy resin
  • Hetero-naphthalene biphenyl bisphenol monomer and preparation method thereof, hetero-naphthalene biphenyl epoxy monomer and preparation method and application thereof, and flame-retardant epoxy resin

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preparation example Construction

[0037] The embodiment of the present invention provides a kind of preparation method of xanthylbiphenyl (being phthalazinone structure) bisphenol monomer, main steps are as follows:

[0038] (1) Friedel-Crafts reaction to prepare one-sided methoxyl intermediate (MHPZ);

[0039] (2) Using MHPZ, BPM (p-bromoanisole), PNTM (1,10-phenanthroline) and CuI (cuprous iodide), the double-sided methoxy intermediate (MMPZ);

[0040] (3) MMPZ is reduced by Lewis acid to obtain dihydroxyl (bisphenol) target monomer (HHPZ);

[0041] Wherein, the synthetic routes of MHPZ, MMPZ and HHPZ are as follows:

[0042]

[0043] The specific synthesis method is as follows:

[0044] (1) The specific method for preparing MHPZ by Friedel-Crafts reaction is as follows:

[0045] In an ice-bath environment, with dichloromethane as the reaction solvent, aluminum trichloride (AlCl 3) as catalyst, reactant PA (phthalic anhydride): AS (methoxybenzene): AlCl 3 The molar ratio between them is 1:1.5:1.5. A...

Embodiment 1

[0057] Embodiment 1 provides a kind of preparation method of the bisphenol monomer containing naphthalene structure, specifically:

[0058] Step (1): The preparation process of the monomethoxyl intermediate (MHPZ) containing the naphthalene structure

[0059] In an ice-bath environment, with dichloromethane as the reaction solvent, aluminum trichloride (AlCl 3 ) as catalyst, reactant (PA:AS:AlCl 3 ) with a molar ratio of 1:1.5:1.5. After the feeding is completed, continue to stir for 1 h in an ice-bath environment, react the above mixed system at 25°C for 3 h, sink into a glacial acid bath after the reaction, and obtain a white solid powder , that is, the intermediate acid (the product of PA and AS). Dissolve the above white solid powder in a mixed solvent of sulfolane and chlorobenzene (volume ratio: 3:1), mix and stir at 110°C for 30 minutes, and then dropwise add the corresponding reactant intermediate acid (product of PA and AS) moles Fractions of hydrazine hydrate were...

Embodiment example 2

[0064] Add MHPZ and K to a three-neck flask equipped with magnetic stirring and reflux condensing device 2 CO 3 , K 2 CO 3 The amount of MHPZ is 2.5 times the molar amount of MHPZ, and the salt-forming reaction is performed at 145°C for 5 to 6 hours. After the salt-forming reaction is completed, the reaction solution is lowered to room temperature, and then the Ullmann coupling ligand PNTM, the catalyst CuI and the reaction solution are added. BPM (when feeding, the molar ratio of MHPZ, BPM, PNTM and CuI is 1:1.5-2:0.01-0.02:0.05-0.15), protected from light for 18 hours, the reaction temperature gradually increased from room temperature to 170 °C. After the reaction is finished, cool the reaction solution and sink into hot water, drain overnight to obtain a brown solid, dissolve the obtained brown solid in chloroform, suction filter the resulting filtrate, add excess anhydrous sodium sulfate to remove water, and obtain a light yellow powder after rotary evaporation solid, w...

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Abstract

The invention firstly provides a hetero-naphthalene biphenyl bisphenol monomer and a preparation method thereof. The preparation method comprises the following steps: (1) preparing a unilateral methoxy intermediate MHPZ through a Friedel-Crafts reaction; (2) synthesizing a double-side methoxy intermediate MMPZ by taking MHPZ, p-bromoanisole, 1, 10-phenanthroline and CuI as raw materials; and (3) reducing the MMPZ by using Lewis acid to obtain a bisphenol monomer HHPZ. The synthesis conditions have the advantages of mild reaction conditions, simple post-treatment of the product and high purityof the product. The two ends of the synthesized bisphenol monomer HHPZ are further subjected to epoxidation with epoxy chloropropane, an epoxy monomer with a low melting point and a wide processing window is obtained, the epoxy monomer can be further used for preparing intrinsic flame-retardant epoxy resin, and the flame-retardant grade can reach the V-0 grade.

Description

technical field [0001] The invention belongs to the field of bisphenol monomers, and in particular relates to a heteronaphthylbiphenyl bisphenol monomer and a preparation method thereof, and also relates to an epoxy monomer containing a heteronaphthylbiphenyl structure, a preparation method and an application thereof. Background technique [0002] Phenolic compounds are the main raw materials for the synthesis of polyarylates, polyaryl ethers, epoxy resins, and polysulfone resins. Special functional groups are introduced into the main chain of the polymer to improve the performance of the polymer (temperature resistance, flame retardancy, etc.) properties, optical properties, wave transmission or absorption properties, etc.). The bisphenol monomer structure contains a rigid nitrogen heterocyclic structure, which can not only improve the heat resistance of the polymer, but also enable the polymer to have intrinsic flame retardancy; at the same time, the nitrogen-containing he...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/32C07D405/14C08G59/26
CPCC07D237/32C07D405/14C08G59/26
Inventor 蹇锡高王锦艳翁志焕刘程宗立率李楠
Owner DALIAN UNIV OF TECH
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