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Norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic acid and ester thereof, method for producing norbornane-2-spiro

A kind of technology of tetracarboxylic dianhydride and norbornane, which can be used in the field of Ming Dynasty and can solve the problems that have not yet been obtained.

Active Publication Date: 2013-01-30
JX NIPPON OIL & ENERGY CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as such an alicyclic polyimide, there has not yet been obtained a material having heat resistance sufficiently comparable to that of the above-mentioned wholly aromatic polyimide (for example, trade name "Kapton").

Method used

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  • Norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic acid and ester thereof, method for producing norbornane-2-spiro
  • Norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic acid and ester thereof, method for producing norbornane-2-spiro
  • Norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride, norbornane-2-spiro-cycloalkanone-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic acid and ester thereof, method for producing norbornane-2-spiro

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0218] 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.

[0219] In addition, in the following, the confirmation of the molecular structure of the compound obtained in each synthesis example and each example is carried out by using an IR detector (manufactured by JASCO Corporation, trade name: FT / IR-460, FT / IR-4100) and NMR A detector (manufactured by VARIAN, trade name: UNITY INOVA-600 and JNM-Lambda500 manufactured by JEOL Ltd.) was used to measure IR and NMR spectra. In addition, the 5% weight loss temperature was measured by heating from room temperature (25°C) at 10°C / min while blowing nitrogen gas using a thermogravimetric analyzer ("TG / DTA220" manufactured by SII NanoTechnology Inc.). The temperature at which the weight of the sample decreases by 5% is obtained. In addition, the glass transition temperature (Tg) is using a differential scanning calor...

Synthetic example 1

[0221] First, 6.83 g (dimethylamine: 75.9 mmol) of the 50 mass % dimethylamine aqueous solution was put into the 100-ml two-necked flask. Next, 8.19 g of 35% by mass aqueous hydrochloric acid (hydrogen chloride: 78.9 mmol) was added to a 100 ml dropping funnel. Next, the above-mentioned dropping funnel was installed on the above-mentioned two-necked flask, and the above-mentioned hydrochloric acid aqueous solution was dropped into the above-mentioned dimethylamine aqueous solution under ice-cooling conditions, and the hydrochloride of dimethylamine was prepared in the above-mentioned two-necked flask. Next, in the above-mentioned two-necked flask, 2.78 g (92.4 mmol) of paraformaldehyde and 2.59 g (30.8 mmol) of cyclopentanone were further added. Next, after attaching a ball head condenser to the above-mentioned two-necked flask, the inside of the above-mentioned two-necked flask was replaced with nitrogen. Afterwards, the above-mentioned two-necked flask was placed in an oil ...

Synthetic example 2

[0227] First, 6.83 g of an aqueous dimethylamine solution (dimethylamine: 75.9 mmol) was added to a 100 ml two-necked flask. Next, 8.19 g of 35% by mass aqueous hydrochloric acid solutions (hydrogen chloride: 78.9 mmol) were added to a 100 ml dropping funnel. Next, the dropping funnel was attached to the two-necked flask, and the aqueous hydrochloric acid solution was dropped into the aqueous dimethylamine solution under ice-cooling to prepare dimethylamine hydrochloride in the two-necked flask. Next, in the above-mentioned two-necked flask, 2.78 g (92.4 mmol) of paraformaldehyde and 3.02 g (30.8 mmol) of cyclohexanone were further added. Next, after attaching a ball head condenser to the above-mentioned two-necked flask, the inside of the above-mentioned two-necked flask was replaced with nitrogen. Afterwards, the above-mentioned two-necked flask was placed in an oil bath of 90° C., and heated and stirred for 4 hours to obtain In the compound n is 3, R 2 , R 3 all are hyd...

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Abstract

Disclosed is a norbornane-2-spiro-a-cycloalkanone-a'-spiro-2''-norbornane-5,5'',6,6''-tetracarboxylic dianhydride represented by general formula (1), wherein n represents an integer of 0 to 12, and R1, R2, and R3 each independently represent a hydrogen atom or the like.

Description

technical field [0001] The present invention relates to norbornane-2-spiro-α-cycloalkanone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic dianhydrides, norbornane- 2-spiro-α-cycloalkanone-α'-spiro-2”-norbornane-5,5”,6,6”-tetracarboxylic acid and its esters, norbornane-2-spiro-α- Method for producing cycloalkanone-α'-spiro-2"-norbornane-5,5",6,6"-tetracarboxylic dianhydrides, polyimide obtained using the same, and polyimide Manufacturing method. Background technique [0002] Tetracarboxylic dianhydrides are generally useful as raw materials for producing polyimide resins, epoxy curing agents, and the like. Among such tetracarboxylic dianhydrides, for example, aromatic tetracarboxylic dianhydrides such as pyromellitic dianhydride are mainly used as raw materials for polyimide resins used in the field of electronic devices and the like. However, such aromatic tetracarboxylic dianhydrides are not sufficient as raw materials for polyimide resins used in the optical field and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C07C69/757C08G73/10C07B61/00
CPCC07C67/38C07C69/757C07C2103/94C08G73/1078C07D493/10C07C235/82C07D407/08C07D487/10C07C2603/94
Inventor 松本利彦小松伸一
Owner JX NIPPON OIL & ENERGY CORP
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