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Transparent polyimide resin and preparation method thereof

A technology of polyimide resin and transparent polyimide, which is applied in the field of transparent polyimide resin and its preparation, can solve the problem that the transparency and heat resistance performance need to be further improved, it cannot be applied on a large scale, and it hinders the electron cloud. Conjugation and other issues to achieve the effects of inhibiting the formation of charge transfer complexes, large free volume, and increasing the glass transition temperature

Active Publication Date: 2014-10-29
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as the colorless and transparent polyimide film material LaRC developed by NASA TM -CP1 and LaRC TM -CP2 uses hexafluorodianhydride (6FDA), see US Patents US4603061 and US4595548, but the price of this dianhydride monomer is expensive
[0007] (3) The use of large side groups or asymmetric structural units hinders the conjugation of electron clouds and inhibits the formation of charge transfer complexes. However, the synthesis of such monomers is difficult and cannot be applied on a large scale.
[0008] In the Chinese invention patent application whose publication number is CN102911359A, it has been reported that the polyamide prepared by polycondensation reaction of 1,4-bis(3,4-dicarboxylic acid phenoxy)cyclohexane dianhydride and dibasic primary amine monomer is reported. Imine, which introduces the structure of cyclohexane into the molecular structure, improves the transparency of polyimide without reducing the reactivity, but its transparency and heat resistance need to be further improved

Method used

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  • Transparent polyimide resin and preparation method thereof
  • Transparent polyimide resin and preparation method thereof
  • Transparent polyimide resin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1: Preparation of 1,4-bis(2,3-dicarboxylic acid phenoxy)cyclohexane dianhydride:

[0065] Under nitrogen protection, add 8.4g (60% solid content, mass percentage, 210mmol) of sodium hydride into a 500mL three-necked flask, then add 100mL of N,N-dimethylformamide, and stir at room temperature for 2 hours. Then dropwise add a mixture of 11.6g (100mmol) of 1,4-cyclohexanediol and 100mL of N,N-dimethylformamide, after stirring at room temperature for 1 hour, add 35.5g (205mmol) The mixed solution of 3-nitrophthalonitrile and 150mL of N,N-dimethylformamide was stirred at room temperature for 3.5 hours after the addition was completed, the reaction solution was poured into water, a precipitate was precipitated, filtered, washed with ethanol, Drying gave crude 1,4-bis(2,3-dicyanophenoxy)cyclohexane.

[0066] The above crude product was heated to reflux in 150 mL of acetonitrile solution, filtered while hot, and the filter residue was dried to obtain 26.7 g of white...

Embodiment 2

[0074] In this embodiment, the transparent polyimide resin material has the following structural formula:

[0075]

[0076] The specific preparation method is: under nitrogen protection, 1.3450g (4.0mmol) of 2,2'-bis(trifluoromethyl)-4,4'-diaminodiphenyl ether, 1.6668g (4.0mmol) of 1, Add 4-bis(2,3-dicarboxylic acid phenoxy)cyclohexanedianhydride and 15ml of m-cresol into a 50mL reaction flask, then add 3 drops of isoquinoline, heat and stir at 190°C for 8 hours to obtain Viscous polyimide solution, when the reaction temperature drops to 60-80°C, dilute with m-cresol and precipitate in ethanol, after suction filtration, boil and wash twice with ethanol under reflux, put it in an oven to dry, and obtain polyimide imide product.

[0077] The inherent viscosity of the polyimide resin prepared in this example is 0.96dL / g, and the glass transition temperature is 245°C.

[0078] The polyimide powder prepared in this embodiment is configured into a solution with a concentration ...

Embodiment 3

[0086] In this embodiment, the transparent polyimide resin material has the following structural formula:

[0087]

[0088] The specific preparation method is: under nitrogen protection, 1.7300g (4.0mmol) of 4,4'-bis(3-aminophenoxy)diphenyl sulfone, 1.6668g (4.0mmol) of 1,4-bis(2 , 3-dicarboxylic acid phenoxy) cyclohexane dianhydride and 15 ml of m-cresol were added to a 50 mL reaction flask, and then 3 drops of isoquinoline were added, heated and stirred at 190°C for 8 hours to obtain a viscous polyamide The imine solution, when the reaction temperature drops to 60-80°C, is diluted with m-cresol and precipitated in ethanol. After suction filtration, the ethanol is refluxed and washed twice, and dried in an oven to obtain a polyimide product.

[0089] The inherent viscosity of the polyimide resin prepared in this embodiment is 0.34dL / g, and the glass transition temperature is 208°C.

[0090] The polyimide powder prepared in this embodiment is configured into a solution wit...

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Abstract

The invention discloses transparent polyimide resin which is obtained through condensation polymerization of a 1, 4-bis(2, 3-dicarboxylphenoxy)cyclohexane dianhydride monomer and a primary diamine monomer. Phthalic anhydride structures at two ends of the dianhydride monomer keep the high reaction activity of dianhydride, and an alicyclic structure with a distorted middle space structure has relatively large free volume and steric hindrance, so that the formation of charge transfer complexes in polyimide molecules and among the molecules is effectively inhibited, and the transparency and glass transition temperature of a polymer are increased. The obtained polyimide resin has the glass transition temperature of 200-300 DEG C, the ultraviolet absorption cutoff wavelength of 370-380nm and the light transmissivity at the wavelength of 450nm of 75-90%. The transparent polyimide resin has a better application prospect in the fields such as flexible substrate materials of solar cells, substrate materials of flexible transparent conducting films, liquid crystal display materials and the like. The invention also discloses a dianhydride monomer which can be used for preparing the transparent polyimide resin.

Description

technical field [0001] The invention relates to the field of polyimide and its preparation, in particular to a transparent polyimide resin and its preparation method. Background technique [0002] Polyimide is the most important variety of aromatic heterocyclic polymers developed in the past half century, and it is also a type of polymer material with the highest service temperature. It has high mechanical strength, high temperature resistance, chemical stability, and creep resistance. With excellent comprehensive performance, it has been widely used in aviation, aerospace, electrical, mechanical, microelectronics, chemical industry and other fields. [0003] Recently, with the development of high-tech industries, the demand for high heat-resistant and high-transmittance polyimide in optical fields such as light guides, waveguides and liquid crystal displays is becoming more and more urgent, because polyimide with high temperature resistance and high light transmission Colo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C07D209/48C07D307/89
Inventor 陈国飞周禹方省众
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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