Preparation method and application of chirality azo polyurethane thermal-optic material

A technology of polyurethane and polyurethane prepolymerization, which is applied in the field of chiral azo polyurethane thermo-optical materials and its preparation, can solve the problems of polymer thermal stability reduction and reduction, achieve improved thermal stability, simple preparation process, and high non-toxicity The effect of linear performance

Inactive Publication Date: 2014-05-28
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Improvement in photo-alignment efficiency of azobenzene-containing polyimide flms, Thin Solid Films, 2009,518:729-734. Reported the preparation of polyimide containing azochromophore in the main chain, and its photoalignment efficiency Research was carried out, and the results showed that the hardness of the polymer main chain was reduced, and the photoalignment efficiency was improved, but the thermal stability of the polymer was reduced;

Method used

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  • Preparation method and application of chirality azo polyurethane thermal-optic material
  • Preparation method and application of chirality azo polyurethane thermal-optic material
  • Preparation method and application of chirality azo polyurethane thermal-optic material

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Embodiment 1

[0027] In a 250mL three-necked flask equipped with a stirring and reflux condenser, 0.66g of 4,4'-bis(6-hydroxyhexyloxy)biphenyl (6BP) was dissolved in 40g of N,N'-diphenyl Methylformamide (DMF), add 0.67g of isophorone diisocyanate (IPDI) and 2 drops of dibutyltin dilaurate (T-12) catalyst to it, react at 90°C for 4h, then add 0.71g of p- Bornyl hydroxyazobenzoate (AZO), continue to react at 90°C for 3h, add 15mL of methanol after the reaction, filter the separated precipitate, wash with 15mL of methanol three times, and vacuum dry at 60°C for 24h to obtain orange-red Chiral azo polyurethane material (CAZOPU-1).

Embodiment 2

[0029] In a 250mL three-necked flask equipped with a stirring and reflux condenser, 1.02g of 4,4'-bis(6-hydroxyhexyloxy)biphenyl (6BP) was dissolved in 65g of N,N'-diphenyl Methylformamide (DMF), add 1.13g of isophorone diisocyanate (IPDI) and 2 drops of dibutyltin dilaurate (T-12) catalyst, react at 90°C for 5h, then add 1.15g of p- Bornyl hydroxyazobenzoate (AZO), continue to react at 90°C for 4h, add 20mL of methanol after the reaction, filter the precipitated precipitate, wash with 20mL of methanol three times, and vacuum dry at 60°C for 30h to obtain orange-red Chiral azo polyurethane material (CAZOPU-2).

Embodiment 3

[0031] In a 250mL three-neck flask equipped with a stirring and reflux condenser, 0.51g of 4,4'-bis(6-hydroxyhexyloxy)biphenyl (6BP) was dissolved in 30g of N,N'-diphenyl Methylformamide (DMF), add 0.53g of isophorone diisocyanate (IPDI) and 2 drops of dibutyltin dilaurate (T-12) catalyst to it, react at 90°C for 4h, then add 0.60g of p- Bornyl hydroxyazobenzoate (AZO), continue to react at 90°C for 3h, add 15mL of methanol after the reaction, filter the precipitated precipitate, wash with 20mL of methanol three times, and vacuum dry at 60°C for 36h to obtain orange-red Chiral azo polyurethane material (CAZOPU-3).

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Abstract

The invention belongs to the field of organic synthesis, relates to a preparation of chirality azo benzene compounds, and in particular to a preparation method and an application of a chirality azo polyurethane thermal-optic material. Diatomic alcohol 4, 4'-di (6-hydroxyhexyloxy) biphenyl (shown as 6BP) which contains a biphenyl structure and isophorone diisocyanate (IPDI) are utilized to be reacted with a catalyst of dibutyltin dilaurate, polyurethane preformed polymer of isocyanic acid root end capping is prepared; and preformed polymer is reacted with hydroxy azo benzoic acid borneol ester (shown as AZO) to prepare the chirality azo polyurethane thermal-optic material. The preparation process is simple, chromophore molecule containing chirality carbon atom is induced into polyurethane, so that central asymmetry of a polyurethane material is realized, and non-linearity property of the polyurethane material is improved; and meanwhile, when polyurethane is prepared, the alcohol biphenyl-typed glycol is selected, thermal stability of the material is improved by the induction of rigidity groups, and the possibility of researching on a novel digital thermal-optic switch which is provided with low driving power is provided.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to the preparation of chiral azobenzene compounds, in particular to a chiral azo polyurethane thermo-optic material and its preparation method and application. Background technique [0002] In recent years, azo compounds as optical information materials have been a very active research direction. Aromatic azo molecules will undergo reversible cis-trans isomerization under light irradiation (or under the action of heat), and in polarization Under the action of light, the orientation rearrangement of molecules can occur. The photoanisotropy and photochromic functions of azobenzene compounds are widely used in optical information storage, optical amplification, optoelectronics, optical computing, optical control of molecular orientation, optical switching, second harmonic generation, photoelectric control, optical Refractive effects, integrated optics, etc. have great application potenti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/75C08G18/38C08G18/32C08G18/10
Inventor 邱凤仙汪青曹智娟杨冬亚叶飞燕
Owner JIANGSU UNIV
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