Benzoxazine-terminated imide, preparation method thereof and polybenzoxazine-terminated imide film

A technology of end-type imide and benzoxazine is applied in the field of polybenzoxazine-terminated imide film, which can solve the problems of low thermal decomposition temperature, inability to meet the requirements of flame retardancy, and stress generation. , to achieve the effect of broad application prospects, meltable and soluble processing, and easy processing

Active Publication Date: 2022-07-29
SOUTH CHINA UNIV OF TECH
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Problems solved by technology

[0002] As a new type of thermosetting resin, benzoxazine has the advantages of good mechanical properties, flame retardancy and heat resistance after curing, and has been widely used in electronic packaging materials, aerospace, flame retardant materials etc., but the best flame retardant performance of the common polybenzoxazine can only reach the U94-V1 level, which cannot meet the requirements of increasingly sophisticated electronic components for flame retardancy
And the thermal decomposition temperature of existing products is low, 330-370°C, which cannot meet the requirements of new aerospace above 400°C
Polybenzoxazine itself has the problem of brittle mechanical properties, and it is easy to break during use
[0003] In the existing research, Zhang Kan et al. synthesized the main chain type benzoxazine through diphenylmethane diamine and bisphenol A, and continued to synthesize oxazine with the diamine obtained after end-capping with o-hydroxyphthalimide Compared with the benzoxazine directly synthesized by the main chain, the thermal weight loss temperature of 5% of the polymer obtained after thermal curing is 404 ° C, which is higher than the thermal weight loss of 42 ° C without o-hydroxyphthalimide end-capping, and can be used at very high It can be used continuously at a high temperature, but the longer main chain makes the monomer unable to be melt-processed, and the preparation process conditions are relatively harsh
Petrakova et al. introduced chlorine atoms into MDA (alkyldiamine) type benzoxazines to obtain U94-V0 level benzoxazines, but the heat resistance dropped significantly from 30°C to 357°C
The glass transition temperature of common benzoxazines is around 200°C. It is easy to soften and deform in a higher temperature environment. For high-precision products, it is easy to generate stress in high and low temperature changes, resulting in cracking

Method used

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  • Benzoxazine-terminated imide, preparation method thereof and polybenzoxazine-terminated imide film
  • Benzoxazine-terminated imide, preparation method thereof and polybenzoxazine-terminated imide film
  • Benzoxazine-terminated imide, preparation method thereof and polybenzoxazine-terminated imide film

Examples

Experimental program
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Embodiment 1

[0046] This example relates to the preparation of small molecule benzoxazine-terminated imides using 4,4'-diaminodiphenyl ether, 4,4'-(hexafluoroisopropene)diphthalic anhydride, phenol and paraformaldehyde and its thermosetting film.

[0047] (1) Pass nitrogen into the reactor equipped with mechanical stirring, nitrogen inlet and outlet and thermometer, mix 15mmol (3.003g) 4,4'-diaminodiphenyl ether and 10mmol (4.442g) 4,4'-( Hexafluoroisopropene) diphthalic anhydride was dissolved in 30 ml of N,N-dimethylformamide (DMF) in a ratio of 1.5:1, and reacted at 15° C. for 3 hours. The reaction product was precipitated in water, and vacuum-dried at 80°C for 12 h to obtain powder.

[0048] (2) put the powder obtained above into a tube furnace, feed nitrogen into the tube furnace, heat up to 350 ° C and solidify into a diamine-terminated imide, because the melting temperature is lower, the diamine-terminated amide The imine is melted and then cooled to form a film, which needs to be...

Embodiment 2

[0056] This example involves the use of 1,4-bis(4-aminophenoxy)benzene, 4,4'-(hexafluoroisopropene)diphthalic anhydride, phenol, and paraformaldehyde to prepare small molecule benzoxazine endcaps type imide and its thermosetting film.

[0057] (1) Pass nitrogen into the reactor equipped with mechanical stirring, nitrogen inlet and outlet and thermometer, and mix 15mmol (4.385g) 1,4-bis(4-aminophenoxy)benzene and 10mmol (4.442g) 4 ,4'-(hexafluoroisopropene)diphthalic anhydride was dissolved in 30 ml of N,N-dimethylformamide (DMF) in a material ratio of 1.5:1, and reacted at 15°C for 3 hours. The reaction product was precipitated in water, and vacuum-dried at 80°C for 12 h to obtain powder.

[0058] (2) put the powder obtained above into a tube furnace, feed nitrogen into the tube furnace, heat up to 350 ° C and solidify into a small molecular amine group terminated imide, because the melting temperature is low, the small molecular amine The base-terminated imide is melted and...

Embodiment 3

[0066] This example involves the use of 1,4-bis(4-aminophenoxy)benzene, 4,4'-(hexafluoroisopropene)diphthalic anhydride, p-trifluorophenol, and paraformaldehyde to prepare small molecule benzoxanes Azine-terminated imides and their thermally cured films.

[0067] (1) feed nitrogen into the reactor equipped with mechanical stirring, nitrogen inlet and outlet and thermometer, 15mmol (4.385g) 1,4-bis (4-aminophenoxy) benzene and 10mmol (4.442g) 4, 4'-(Hexafluoroisopropene)diphthalic anhydride was dissolved in 30 ml of N,N-dimethylformamide (DMF) in a substance ratio of 1.5:1, and reacted at 15° C. for 3 hours. The reaction product was precipitated in water, and vacuum-dried at 80°C for 12 h to obtain powder.

[0068] (2) put the powder obtained above into a tube furnace, feed nitrogen into the tube furnace, heat up to 350 ° C and solidify into a small molecular amine group terminated imide, because the melting temperature is low, the small molecular amine The base-terminated im...

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Abstract

The invention discloses benzoxazine end-capped imide which is obtained by reacting diamine end-capped imide serving as an amine source with monohydric phenol and paraformaldehyde, the diamine-terminated imide is obtained by thermal cyclization of micromolecular polyamide acid in inert gas; the micromolecular polyamide acid is prepared by condensation reaction of a dianhydride monomer and a diamine monomer. The invention further discloses a preparation method of the benzoxazine end-capped imide and a polybenzoxazine end-capped imide film prepared from the benzoxazine end-capped imide. The invention further discloses a preparation method of the benzoxazine end-capped imide and a polybenzoxazine end-capped imide film prepared from the benzoxazine end-capped imide. The benzoxazine-terminated imide disclosed by the invention is fusible and soluble, and is easy to process; the polybenzoxazine-terminated imide film has the advantages of being excellent in mechanical property, thermal stability and flame retardant property.

Description

technical field [0001] The invention relates to the technical field of organic materials, in particular to a benzoxazine-terminated imide, a preparation method thereof, and a polybenzoxazine-terminated imide film. Background technique [0002] Benzoxazine is a new type of thermosetting resin. The cured polybenzoxazine has the advantages of good mechanical properties, flame retardant properties and heat resistance. It has been widely used in electronic packaging materials, aerospace, and flame retardant materials. etc., but the current common polybenzoxazine with the best flame retardant performance can only reach the U94-V1 level, which cannot meet the requirements of increasingly sophisticated electronic components for flame retardancy. And the thermal decomposition temperature of the existing products is low, 330-370 ℃, which cannot meet the requirements of 400 ℃ above the new aerospace. Polybenzoxazine itself has the problem of brittle mechanical properties, and it is ea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C08J5/18C08L79/08
CPCC08G73/1071C08G73/1039C08G73/1028C08J5/18C08J2379/08
Inventor 邱志明林克华严玉蓉郭熙桃
Owner SOUTH CHINA UNIV OF TECH
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