Triazine-containing benzoxazine, triazine-containing benzoxazine polymer, and preparation method thereof

A polycyclic benzoxazine and phenyl technology, applied in the field of polymer materials, can solve the problems of unsatisfactory improvement of cyano group conversion rate, unfavorable performance of polybenzoxazine, and low cyano group conversion rate, etc. Achieve the effects of simple and easy curing process, excellent thermal performance and low curing temperature

Active Publication Date: 2011-10-19
SHANDONG UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The main disadvantage of this method is that the conversion rate of cyano groups is not high (conversion rate <40%). The possible reason is that the cross-linked molecular chain network formed by curing limits the movement of cyano groups, so that no matter whether it is used to increase the curing temperature or add Catalysts and other methods cannot satisfactorily improve the conversion rate of cyano groups, and the content of triazine rings in the final product polybenzoxazine is relatively low, which is unfavorable for improving the performance of polybenzoxazine

Method used

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  • Triazine-containing benzoxazine, triazine-containing benzoxazine polymer, and preparation method thereof
  • Triazine-containing benzoxazine, triazine-containing benzoxazine polymer, and preparation method thereof
  • Triazine-containing benzoxazine, triazine-containing benzoxazine polymer, and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0049] Synthesis of embodiment 1 triazine-containing polycyclic benzoxazine monomer (BZ-a)

[0050] Synthesis of trihydric phenol (TP) containing triazine ring: add 10.0g p-cyanophenol, 1.8mL trifluoromethanesulfonic acid and 40mL dichloromethane to a 100mL flask successively, and react at room temperature for 2h to obtain a yellow suspension liquid. Wash several times with 1N NaOH aqueous solution and deionized water, let stand to separate layers, take dichloromethane and concentrate to obtain a white solid. Yield 92%.

[0051] 1 H NMR (300MHz, CDCl 3 , ppm): 6.97 (d, 6H, Ph-H), 8.55 (d, 6H, Ph-H), 10.29 (s, 3H, Ph-O-H).

[0052] Synthesis of triazine-containing polycyclic benzoxazine monomer (BZ-a): 1.0g TP, 0.504g paraformaldehyde, 0.76mL aniline, 0.5mL triethylamine, 50mL anhydrous Ethanol, stirred and miscible, gradually warmed to reflux, and reacted at reflux temperature for 4 hours to obtain a yellow benzoxazine monomer solution. The reaction mixture was evaporate...

Embodiment 2

[0054] Synthesis of embodiment 2 triazine-containing polycyclic benzoxazine monomer (BZ-a)

[0055] Synthesis of trihydric phenol (TP) containing a triazine ring: 10.0 g of p-cyanophenol, 1.6 mL of trifluoroacetic acid, and 40 mL of dichloromethane were sequentially added to a 100 mL flask, and reacted at room temperature for 3 h to obtain a yellow suspension. Wash several times with 1N NaOH aqueous solution and deionized water, let stand to separate layers, take dichloromethane and concentrate to obtain a white solid. Yield 90%.

[0056] 1 H NMR (300MHz, CDCl 3 , ppm): 6.97 (d, 6H, Ph-H), 8.55 (d, 6H, Ph-H), 10.29 (s, 3H, Ph-O-H).

[0057] Synthesis of triazine-containing polycyclic benzoxazine monomer (BZ-a): 1.0g TP, 1.36mL 37% formaldehyde aqueous solution, 0.76mL aniline, 0.5mL triethylamine, 30mL di Oxyhexane, stirred and miscible, gradually raised the temperature to reflux, and reacted at reflux temperature for 3 hours to obtain a yellow benzoxazine monomer solution...

Embodiment 3

[0058] Synthesis of embodiment 3 triazine-containing polycyclic benzoxazine monomer (BZ-a)

[0059] Synthesis of trihydric phenol (TP) containing a triazine ring: Add 10.0 g of p-cyanophenol, 1.6 mL of trifluoroacetic acid, and 35 mL of chloroform in sequence in a 100 mL flask, and react at room temperature for 2 h to obtain a yellow suspension. Wash several times with 1N NaOH aqueous solution and deionized water, let stand to separate layers, take dichloromethane and concentrate to obtain a white solid. Yield 93%.

[0060] 1 H NMR (300MHz, CDCl 3 , ppm): 6.97 (d, 6H, Ph-H), 8.55 (d, 6H, Ph-H), 10.29 (s, 3H, Ph-O-H).

[0061] Synthesis of triazine-containing polycyclic benzoxazine monomer (BZ-a): 1.0g TP, 1.36mL 37% formaldehyde aqueous solution, 0.76mL aniline, 0.5mL triethylamine, 30mL di Oxyhexane, stirred and miscible, gradually raised the temperature to reflux, and reacted at reflux temperature for 3 hours to obtain a yellow benzoxazine monomer solution. The reaction...

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Abstract

The invention relates to triazine-containing benzoxazine, a triazine-containing benzoxazine polymer, and a preparation method thereof. The preparation method is characterized by: adopting cyanophenol as a raw material; adopting trifluoromethanesulfonic acid or trifluoroacetic acid as a catalyst; synthesizing triazine-containing trihydric phenol (TP for short) in dichloromethane or chloroform or acetone at a common temperature; adopting the synthesized TP, formaldehyde and aminated compounds as reaction raw materials; adopting a alkali as the catalyst, and carrying out a reaction in a alcohol solvent or a ether solvent to synthesize a series of triazine-containing polycyclic benzoxazine monomers (BZ for short) which have not been reported; heating the BZ to carry out a ring-opening polymerization to form polybenzoxazine (PBZ for short). A structural formula of the monomer BZ is shown as follow, substituents R are shown in the specification. The synthesized novel monomer provided by the present invention contains a triazine ring structure, such that the triazine content in the PBZ resin can be substantially raised so as to notably improve heat resistance, residual carbon rate, fire resistance property and wave transmission property of the PBZ.

Description

technical field [0001] The invention relates to a novel benzoxazine monomer and polymer thereof, in particular to triazine-containing benzoxazines, polybenzoxazines and their preparation methods, belonging to the technical field of polymer materials. Background technique [0002] Polybenzoxazine has excellent mechanical properties, heat resistance, flame retardancy and electrical insulation properties, and has received extensive attention and research in recent years. However, with the development of high and new technologies such as aerospace, electronic appliances, and information technology, the requirements for material performance are also getting higher and higher. Need to develop high glass transition temperature (T g ), high thermal stability and high flame retardancy and other high-performance polybenzoxazines. [0003] It is well known that triazine rings have high thermal stability and flame retardancy. Therefore, the introduction of triazine rings into polyben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C08G73/06
Inventor 鲁在君王登霞张耀亨张广照
Owner SHANDONG UNIV
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