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Deuterated polyimides and derivatives thereof

A technology of deuterated polyimide and deuterated polyamide, applied in organic chemistry, instrumentation, optics, etc., can solve problems such as low refractive index of fluorinated polyimide compound, brittle and easy-to-break film, low humidity, etc. , to achieve the effects of excellent low moisture absorption, low light transmission loss, and excellent heat resistance

Inactive Publication Date: 2007-05-02
WAKO PURE CHEMICAL INDUSTRIES
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorinated polyimide compounds are attracting attention as polymer materials for optical waveguides due to their low light transmission loss in the near-infrared region, excellent heat resistance, and low humidity. However, due to their low refractive index, fluorinated polyimide compounds In the case of using it as the core of an optical waveguide, it is necessary to use a cladding having a refractive index suitable for the core, and as a result, there is a problem that the materials that can be used as the cladding are limited
In addition, if the fluorination rate of the fluorinated polyimide compound is too low, the above-mentioned problems of transparency and light transmission loss due to the C-H bond will appear, and if the fluorination rate is too high, the compound will The surface tension of the compound is reduced, which will lead to the deterioration of the adhesion with the substrate / substrate, and the difficulty of processing such as coating, and the film formed by the compound has poor adhesion, resulting in a decrease in film properties and the film itself becomes brittle. broken problem

Method used

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  • Deuterated polyimides and derivatives thereof
  • Deuterated polyimides and derivatives thereof
  • Deuterated polyimides and derivatives thereof

Examples

Experimental program
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Effect test

reference example 1

[0198] Reference example 1. The synthesis of deuterated o-toluidine (o-tolidine)

[0199] 20g o-toluidine, and 6g mixed catalyst consisting of 10% Pd / C of 2g and 5% Pt / C of 4g were added to 680mL heavy water (D 2 O), react at about 180° C. for 24 hours. After the reaction, the reaction solution was extracted with ethyl acetate, and then the mixed catalyst was removed by filtration. The resulting filtrate was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 15.4 g of deuterated o-toluidine (yield 77%). Determination of the resulting heavy hydrogenated o-toluidine 1 H-NMR and 2 H-NMR spectrum and structural analysis showed that the average deuterium hydrogenation rate was 82%.

Embodiment 1

[0200] Embodiment 1. the synthesis of deuterated polyamic acid compound

[0201] 2.364g (10mmol) of deuterated o-toluidine obtained in Reference Example 1 and 2.182g (10mmol) of pyromellitic dianhydride were added to 41g of dimethylacetamide and reacted at about 25°C for about 2 hours Afterwards, it was treated by a conventional method to obtain 4.0 g of a deuterated polyamic acid compound (weight average molecular weight: 168000, yield: 88%) containing the following repeating structure.

[0202]

[0203] Measure the IR spectrum of the compound obtained, the result is at 3000cm -1 The nearby peak based on the C-H bond of the aromatic ring is small, which shows that the obtained compound has a very small number of C-H bonds. In addition, the obtained heavy hydrogenated polyamic acid compound was measured 1 H-NMR and 2 H-NMR spectrum and structural analysis showed that the average deuterated hydrogenation rate was 70%.

Embodiment 2

[0204] Embodiment 2. The synthesis of deuterated polyimide compound

[0205] 10 wt% dimethylacetamide solution of 1 g of the deuterated polyamic acid compound obtained in Example 1 was poured on a glass dish, and after heating at about 200° C. for about 1 hour, it was then reacted at about 300° C. for about 1 hours, 0.09 g of a deuterated polyimide compound having the following repeating structure was obtained (yield 90%).

[0206]

[0207] Measure the IR spectrum of the gained deuterated polyimide compound, and carry out structural analysis, the result has seen the peak based on the C=O bond of polyimide structure and the C-N bond (respectively at 1730cm -1 Nearby, 1370cm -1 Nearby), it was determined that the raw material deuterated polyamic acid compound was ring-closed and the target polyimide compound was obtained.

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Abstract

The invention relates to polyimides and derivatives thereof useful as the raw material of polymers for optical waveguides which are excellent in transparency, the resistance to moisture absorption, and heat resistance, and exhibit low optical transmission losses, high refractive indexes, and good tight adhesion to substrates or the like; and application thereof. The polyimides are deuterated ones represented by the general formula [1] (wherein m is an integer of 1 or above; R<1> is a tetravalent alicyclic or aromatic hydrocarbon group which may be deuterated; and R<2> is a deuterated divalent aromatic hydrocarbon group), which are obtained by ring-closing a deuterated polyamic acid represented by the general formula [2] (wherein R<1> and R<2> are each as defined above; and n is an integer of 1 or above) which is produced by reacting an optionally deuterated acid anhydride with a deuterated diamine.

Description

technical field [0001] The present invention relates to a novel deuterated polyimide compound and its derivatives which are useful as raw materials for optical waveguides excellent in heat resistance, transparency, substrate adhesion, and processability. Background technique [0002] Conventionally, glass products have been used as optical waveguides, but since their manufacture requires a high-temperature process exceeding 1000°C, studies are underway to replace glass with polymer materials as optical waveguide materials. In recent years, polyimide compounds have attracted attention as a polymer for optical waveguides, but since a large number of C-H bonds exist in light hydrogen polyimide compounds, polymers containing this compound have poor transparency, and in Light transmission loss is large in the near-infrared region. Therefore, such a polyimide compound cannot be said to be ideal as an optical waveguide material used in a large-capacity high-speed transmission syst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10G02B6/12C07D209/48C07D487/04
CPCC07D209/48G02B6/1221C07D487/04C08G73/1007C08G73/10
Inventor 无藤和重前泽典明伊藤伸浩绵引勉广田耕作佐治木弘尚
Owner WAKO PURE CHEMICAL INDUSTRIES