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Polyimide, and alicyclic tetracarboxylic acid dianhydride for use in production of same

A technology of tetracarboxylic dianhydride and polyimide, applied in the direction of organic chemistry, etc., can solve problems such as difficulty, difficulty in practical application, and polyimide polymerizability is not necessarily sufficient, and achieve light transmittance or heat resistance. The effect of excellent performance and low coefficient of linear expansion

Active Publication Date: 2015-04-29
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since trans-1,4-cyclohexanediamine (t-CHDA) used in the manufacture of such alicyclic polyimide forms a very strong salt at the initial stage of polymerization with PMDA or BPDA Monomer, therefore, it is extremely difficult to polymerize by the usual method, and the polymerizability of this polyimide is not necessarily sufficient, so it is difficult to put it into practical use

Method used

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  • Polyimide, and alicyclic tetracarboxylic acid dianhydride for use in production of same
  • Polyimide, and alicyclic tetracarboxylic acid dianhydride for use in production of same
  • Polyimide, and alicyclic tetracarboxylic acid dianhydride for use in production of same

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Embodiment

[0230] Hereinafter, although this invention is demonstrated more concretely based on an Example and a comparative example, this invention is not limited to a following example.

[0231] First, methods for evaluating properties of compounds, thin films, and the like obtained in each synthesis example, each example, and each comparative example will be described.

[0232]

[0233] The identification of the molecular structure of the compound obtained in each synthesis example and each example etc. is by using an infrared spectroscopic analyzer (manufactured by JASCO Corporation, FT / IR-460, FT / IR-4100, manufactured by Thermo Fisher Scientific K.K., NICOLET 380FT-IR) and an NMR measuring machine (manufactured by VARIAN, trade name: UNITY INOVA-600 and JNM-Lambda 500 manufactured by JEOL Ltd.) to measure IR and NMR spectra.

[0234]

[0235] The identification of the isomer type of the compound obtained in each synthesis example and each Example etc. was performed by HPLC measu...

Synthetic example 1

[0248] (Synthesis Example 1: Preparation of 5-norbornene-2-spiro-α-cyclopentanone-α’-spiro-2”-5”-norbornene)

[0249] First, 61.7g (0.757mol) of dimethylamine hydrochloride, 182g (2.46mol) of 1,3-dioxolane, and 25.9g (0.308mol) of cyclopentanone were added to a 2L three-necked flask , 4.0 g (38 mmol) of 35% hydrochloric acid. Next, after attaching a spherical condenser to the three-necked flask, the internal atmosphere of the three-necked flask was replaced with nitrogen. Thereafter, the three-necked flask was submerged in an oil bath at 90° C., heated and stirred for 5 hours to obtain a mixture containing the Mannich base (represented by the general formula (I-2) described in the above reaction formula (I). The compound [n in general formula (I-2) is 2, R 2 and R 3 are hydrogen, R are methyl, and X - For the compound of chloride ion]) reaction solution. In addition, gas chromatographic analysis (GC analysis: using Agilent Technologies Inc. trade name "6890N" as a detecto...

Synthetic example 2

[0254] (Synthesis Example 2: Preparation of norbornane-2-spiro-α-cyclopentanone-α’-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic acid tetramethyl ester)

[0255] Add methanol (600ml) and 61.1g (454mmol) of CuCl 2 (II), 26.0 g (108 mmol) of 5-norbornene-2-spiro-α-cyclopentanone-α'-spiro-2”-5”-norbornene obtained in Synthesis Example 1 and 243 mg (1.08 mmol) of Pd(OAc) 2 After obtaining the mixed solution, the container was sealed, and the atmosphere inside was replaced with nitrogen. Next, while introducing carbon monoxide into the container, the mixed liquid was stirred at 20° C. and 0.9 MPa for 5 hours to obtain a reaction liquid. Next, carbon monoxide was removed from the inside of the container, and the reaction liquid was concentrated with an evaporator, whereby methanol was removed from the reaction liquid to obtain a reaction product. Thereafter, toluene (900 ml) and 5% by mass hydrochloric acid (900 ml) were added to the reaction product, and vigorously stirred at 80...

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Abstract

A polyimide which contains a repeating unit represented by general formula (1) and / or a repeating unit represented by general formula (2) [wherein R1, R2 and R3 independently represent a hydrogen atom or the like; R4 represents an aryl group having 6 to 40 carbon atoms; and n represents an integer of 0 to 12], wherein the ratio of the total amount of the repeating unit represented by general formula (1) and the repeating unit represented by general formula (2) to the total amount of all of repeating units is 90 mol% or more.

Description

technical field [0001] The present invention relates to an alicyclic tetracarboxylic dianhydride used in polyimide and its manufacture. Background technique [0002] In recent years, research and development of heat-resistant materials have been actively carried out, and polyimides have attracted attention from the viewpoint of being excellent in heat resistance and dimensional stability. Regarding such polyimides, as polyimides having the highest level of heat resistance among heat-resistant polymers, there is aromatic polyimide, a representative organic material developed by DuPont in the United States in the 1960s and commercially available. Imine "Kapton", this aromatic polyimide is known to be a polymer material that can withstand a high temperature of about 300°C or a harsh space environment for a long time. However, such a wholly aromatic polyimide is brown in color due to the intramolecular charge transfer (CT) between the aromatic tetracarboxylic dianhydride unit a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C07D493/10
CPCC07D493/10C08G73/10C08G73/1078C07C2603/93C08G73/1075C08G73/1007C08G73/1067
Inventor 小松伸一藤代理惠子藤原实希渡部大辅椎桥彬松本隆也
Owner UBE IND LTD
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