Benzoxazine intermediate containing sulfonyl polyphenol and preparation method and use thereof

A technology of benzoxazine and intermediate, applied in the field of thermosetting resin and its preparation, can solve the problems of poor solubility, high curing temperature, easy precipitation, etc., and achieve the effect of low cost and excellent flame retardancy

Active Publication Date: 2013-12-04
SICHUAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the research work on benzoxazine resins continues to deepen, the application fields continue to expand, and various types of benzoxazine resins continue to emerge, but benzoxazine resins still generally have high prices, poor solubility, easy precipitation, and high curing temperature. High, flame retardancy and heat resistance need to be further improved, which limits the industrial application of benzoxazine resin to a large extent

Method used

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  • Benzoxazine intermediate containing sulfonyl polyphenol and preparation method and use thereof
  • Benzoxazine intermediate containing sulfonyl polyphenol and preparation method and use thereof
  • Benzoxazine intermediate containing sulfonyl polyphenol and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 24 grams of paraformaldehyde, 28 grams of toluene, 56 grams of ethanol and 4,4-dihydroxydiphenylsulfone 79.97%, 2,4-dihydroxydiphenylsulfone and 2,2-dihydroxydiphenylsulfone 15.25%, three Add 50 grams of sulfone group-containing polyphenols containing 3.41% hydroxytriphenyldisulfone and tetrahydroxytetraphenyltrisulfone to a three-necked bottle for dissolution, and adjust the pH value to 9 with NaOH solution. Then, a mixed solution of 28 g of toluene and 37.2 g of aniline was added dropwise at a temperature of 70° C. for 2 hours. React at a temperature of 80° C. for 6 h, and wash with water to obtain a light brown transparent solution of a sulfone group-containing polyphenol type benzoxazine intermediate. Infrared spectrum characterization: oxazine ring (923cm -1 ), sulfone group (1139cm -1 and 1298cm -1 ); NMR characterization: 4.75ppm (Ar-CH 2 -N) and 5.54ppm (O-CH 2-N). The gelation time at 180°C was 7 minutes and 18 seconds; the exothermic peak temperature of ...

Embodiment 2

[0047] 35 grams of paraformaldehyde, 170 grams of ethanol and 4,4-dihydroxydiphenylsulfone 76.97%, 2,4-dihydroxydiphenylsulfone and 2,2-dihydroxydiphenylsulfone 17.25%, trihydroxytriphenylsulfone Add 75 grams of sulfone group-containing polyphenols of 4.12% disulfone and tetrahydroxytetraphenyltrisulfone into a three-necked bottle for dissolution, and adjust the pH value to 9 with NaOH solution. Then 55 g of aniline were added. Raise the temperature to 50°C for 1 h, then raise the temperature to the boiling point of ethanol for 5 h, cool to room temperature after the reaction, the solid product precipitates, filters, washes, and dries to obtain a light yellow powder. The gelation time at 180°C was 5 minutes and 13 seconds.

Embodiment 3

[0049] Paraformaldehyde 75 grams, dioxane 230 grams and 4,4-dihydroxydiphenyl sulfone 73.07%, 2,4-dihydroxydiphenyl sulfone and 2,2-dihydroxydiphenyl sulfone 17.75%, trihydroxy Add 150 grams of sulfone group-containing polyphenols of 7.90% triphenyldisulfone and tetrahydroxytetraphenyltrisulfone into a three-necked bottle for dissolution, and adjust the pH value to 9 with NaOH solution. Then 110 g of aniline were added. Raise the temperature to 50°C for 1 hour, then raise the temperature to 80°C for 5 hours, cool to room temperature after the reaction, the solid product is precipitated, filtered, washed, and dried to obtain a light yellow powder. The gelation time at 180°C was 3 minutes and 48 seconds.

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Abstract

The invention discloses a benzoxazine intermediate containing sulfonyl polyphenol and a preparation method and use thereof. The preparation method is characterized by comprising the following steps: adding 39 to 55 weight parts of mixture containing sulfonyl polyphenol and 15 to 35 weight parts of formaldehyde into 20 to 120 weight parts of solvent, allowing the mixture containing sulfonyl polyphenol and formaldehyde to dissolve at 20 to 70 DEG C, regulating the pH value with alkaline solution to 8 to 10, and reacting the mixture containing sulfonyl polyphenol with formaldehyde for 0.1 to 3 hours at 20 to 70 DEG C; adding 24 to 45 weight parts of primary amine compound and 0 to 100 weight parts of solvent into the solution, and reacting at 50 to 105 DEG C for 2 to 12 hours; and thus obtaining a solution of benzoxazine resin containing sulfonyl polyphenol, or obtaining solid benzoxazine resin containing sulfonyl polyphenol by removing solvent. The composite prepared by using the intermediate has high flame retardance, high heat resistance and high mechanical performance and can be used as a high-temperature-resistance electric-insulation material or structural material or friction material.

Description

technical field [0001] The invention relates to a sulfone group-containing polyphenol type benzoxazine intermediate, a preparation method and application thereof, and belongs to the field of thermosetting resins and the preparation thereof. Background technique [0002] Benzoxazines are a class of high-performance thermosetting resins with excellent process characteristics and performance. The benzoxazine intermediate has no small molecule release and small shrinkage during the curing process; the benzoxazine cured product has the advantages of high heat resistance, high mechanical properties and low water absorption; in addition, using the structure and properties of benzoxazine By synthesizing benzoxazine intermediates containing different groups, the performance of the cured product can be greatly improved. [0003] Since the 1990s, extensive research has been carried out at home and abroad on the synthesis of benzoxazine intermediates, ring-opening polymerization, struc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/06C08L79/04C08L61/06C08L63/00C08L79/08C08K3/00C08K7/14C08K7/06H01B3/30C09K3/14
Inventor 顾宜赵嘉成冉起超朱蓉琪顾维科盛兆碧凌红
Owner SICHUAN UNIV
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