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Calixarene compound, curable composition and cured product

A technology of calixarene and compound, applied in the field of calixarene compound, can solve the problem of insufficient performance and the like

Active Publication Date: 2020-12-18
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these curable resin compositions do not have sufficient performance for applications requiring miniaturization and high functionality as described above.

Method used

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  • Calixarene compound, curable composition and cured product
  • Calixarene compound, curable composition and cured product
  • Calixarene compound, curable composition and cured product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0268] The following production examples and examples are given to describe the present invention more specifically, but the present invention is not limited to these examples. Parts and % in the examples are all based on mass unless otherwise specified.

[0269] The structure of product (calixarene compound) is determined by measuring according to the following conditions 1 H-NMR, 13 C-NMR, FD-MS performed.

[0270] 1 H-NMR was measured under the following conditions using "JNM-ECM400S" manufactured by JEOL RESONANCE.

[0271] Magnetic field strength: 400MHz

[0272] Number of points: 16 times

[0273] Solvent: deuterated chloroform

[0274] Sample concentration: 2mg / 0.5ml

[0275] 13 C-NMR was measured under the following conditions using "JNM-ECM400S" manufactured by JEOL RESONANCE.

[0276] Magnetic field strength: 100MHz

[0277] Number of points: 1000 times

[0278] Solvent: deuterated chloroform

[0279] Sample concentration: 2mg / ...

Synthetic example 1

[0288] In a 20L separate four-neck flask equipped with a stirring device, a thermometer and a reflux cooling tube, quickly add tert-butyl calix[4]arene 1000g (1.54mol), phenol 1159g (12.32mol) and dehydrated toluene 9375ml, under nitrogen Flow down and stir at 300 rpm. The raw material tert-butylcalix[4]arene was suspended without being dissolved. Next, 1643 g (12.32 mol) of anhydrous aluminum chloride (III) was added in portions while cooling the flask on ice. The solution became a light orange transparent solution, and anhydrous aluminum(III) chloride precipitated at the bottom. After reacting at room temperature for 5 hours, the contents were transferred to a 1 L beaker, and 20 Kg of ice, 10 L of 1N hydrochloric acid, and 20 L of chloroform were added to terminate the reaction. Become a pale yellow transparent solution. The reaction mixture was transferred to a separatory funnel, and the organic layer was separated. Next, the aqueous layer was extracted three times wi...

Synthetic example 2

[0292] Add 205 g (1.52 mol) of n-hexanoyl chloride and 709 g (9.44 mol) of nitroethane into a 2L four-necked flask equipped with a stirring device, a thermometer, and a reflux cooling tube, and stir. Next, while ice-bathing the flask, 243 g (1.82 mol) of anhydrous aluminum chloride (III) was charged in several portions. The solution became a light orange transparent solution. After stirring at room temperature for 30 minutes, the intermediate (α-1) was added in divided portions at 100 g (0.236 mol). The reaction proceeded while foaming, and an orange transparent solution was obtained. After reacting at room temperature for 5 hours, the contents were slowly transferred to a 2 L beaker to which 450 ml of chloroform and 956 g of ice water were added to stop the reaction. Next, after adding 1N hydrochloric acid until the pH reached 1, the reaction mixture was transferred to a separatory funnel, and the organic layer was separated. Next, the aqueous layer was extracted three t...

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PUM

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Abstract

A calixarene compound represented by structural formula (1). In the formula, R1 and R2 independently represent a structural part (A) having a functional group (I), a structural part (B) having a functional group (II) having a carbon-carbon unsaturated bond (excluding a maleate group), a structural part (C) having both of the functional groups (I) and (II), a monovalent organic group (D) having 1-20 carbon atoms other than the structural parts (A), (B) and (C), or a hydrogen atom (E), provided that at least one of a plurality of R2s represents the structural part (A), the structural part (B), the structural part (C) or the organic group (D). When the functional group (I) is a cyano group, an acetylacetonate group, an oxalate group or a malonate group, at least one of the plurality of R1s and R2s represents the structural part (C), or at least one of the plurality of R1s and R2s represents the structural part (A) and at least one of the same represents the structural part (B). When the functional group (I) is a maleate group, at least one of the plurality of R1s and R2s represents the structural part (A) or the structural part (C).

Description

technical field [0001] The present invention relates to a calixarene compound having a novel structure, a curable composition containing the calixarene compound, and a cured product of the curable composition. Background technique [0002] Calixarene is a cyclic oligomer (macrocyclic phenol resin derivative) produced by condensation of phenol and formaldehyde. Calixarene and its derivatives are known to have inclusion functions similarly to crown ethers and cyclodextrins because the benzene ring has a unique structure in which the Holy Grail is reversed. Therefore, in recent years, studies on the use of calixarene and its derivatives as third host molecules (for example, studies aimed at recovering heavy metal ions in seawater, etc.) have been actively carried out. However, practical use has not yet been achieved except for a part. [0003] On the other hand, in products such as semiconductor devices such as ICs and LSIs, and display devices such as thin displays, a film o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/13C07C255/15C07C255/23C08F16/12C08F20/30C08F20/42
CPCC08F16/12C07C255/13C07C69/732C07C69/38C07C69/54C07C43/2055C07C43/23C07C2601/18C07F7/1804C07C2603/90C07C69/36C07C69/593C07C69/716C07C255/23C08F20/30C08F20/34
Inventor 山本辰弥宫本正纪甲斐英知今田知之门本丰
Owner DIC CORP
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