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Calixarene compound, curable composition, and cured product

A curable composition and compound technology, applied in organic chemistry and other fields, can solve the problems of low substrate adhesion, hard but brittle, high crystallinity, etc., and achieve excellent performance

Active Publication Date: 2020-05-05
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As mentioned above, the calixarene compound is a compound that can expect excellent effects such as heat resistance and fastness, but on the other hand, it has problems such as high crystallinity, hard but brittle, and low adhesion to the substrate. The aforementioned patent The calixarene compounds described in Documents 1 and 2 also have these problems

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

[0152] Hereinafter, the present invention will be described more specifically with reference to production examples and examples, but the present invention is not limited to these examples. Parts and % in examples are all based on mass unless otherwise specified.

[0153] For the structural identification of product (calixarene compound), by determining with the following conditions 1 H-NMR, 13 C-NMR, FD-MS to carry out.

[0154] for 1 H-NMR was measured using "JNM-ECM400S" manufactured by JEOL RESONANCE under the following conditions.

[0155] Magnetic field strength: 400MHz

[0156] Cumulative times: 16 times

[0157] Solvent: deuterated chloroform

[0158] Sample concentration: 2mg / 0.5ml

[0159] for 13 C-NMR was measured using "JNM-ECM400S" manufactured by JEOL RESONANCE under the following conditions.

[0160] Magnetic field strength: 100MHz

[0161] Cumulative times: 1000 times

[0162] Solvent: deuterated chloroform

[0163] Sample concentration: 2mg / 0.5ml ...

Synthetic example 1

[0169] Synthesis Example 1: Synthesis of Intermediate (α-1)

[0170] In a 20L detachable four-necked flask equipped with a stirring device, a thermometer and a reflux condenser, 1000 g (1.54 mol) of tert-butyl calix [4] arene, 1159 g (12.32 mol) of phenol and 9375 ml of dehydrated toluene were dropped into rapidly. Stirring was performed at 300 rpm under nitrogen flow. The tert-butylcalix[4]arene as a raw material was suspended without being dissolved. Next, 1643 g (12.32 mol) of anhydrous aluminum chloride (III) was charged into the flask in portions while ice-bathing the flask. The solution turned into 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 1L beaker, and 20Kg of ice, 10L of 1N hydrochloric acid, and 20L of chloroform were added to quench the reaction. It becomes a pale yellow transparent solution. The reaction mixture was tran...

Synthetic example 2

[0172] Synthesis Example 2: R 4 import(1) of (d1)

[0173] 205 g (1.52 mol) of n-hexanoyl chloride and 709 g (9.44 mol) of nitroethane were placed in a 2 L four-necked flask equipped with a stirring device, a thermometer, and a reflux condenser, and stirred. Next, 243 g (1.82 mol) of anhydrous aluminum chloride (III) was charged in portions while ice-bathing the flask. The solution turned into a pale orange transparent solution. Stirring was performed at room temperature for 30 minutes, and the intermediate body (α-1) was charged in multiple portions of 100 g (0.236 mol) at a time. The reaction proceeded while bubbling, and turned into an orange transparent solution. After reacting at room temperature for 5 hours, the contents were slowly transferred to a 2 L beaker containing 450 ml of chloroform and 956 g of ice water to stop the reaction. Next, after adding 1N hydrochloric acid until the pH became 1, the reaction mixture was transferred to a separating funnel, and the o...

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Abstract

The present invention provides a calixarene compound represented by formula (1) [R1 represents a structural moiety (A) having -CH2OH, a structural moiety (B) having a carbon-carbon unsaturated bond, astructural moiety (C) having -CH2OH and a carbon-carbon unsaturated bond, a monovalent organic group (D) other than (A), (B), and (C), or a hydrogen atom (E), R2 represents (A), (B), (C), (D), or (E)(however, excluding the case where all R2s are (E)), R3 represents a hydrogen atom, an aliphatic hydrocarbon group, or an aryl group, n represents 2-10, and * represents a bonding site to the aromatic ring], wherein the calixarene compound contains at least one -CH2OH or phenolic hydroxyl group and at least one carbon-carbon unsaturated bond per molecule; a curable composition containing the calixarene compound; and a cured product of the curable composition.

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 thereof. Background technique [0002] Calixarene compounds are expected to have excellent effects such as heat resistance and fastness due to their unique structures, and therefore various studies have been conducted for various applications such as special coatings and resist materials. As a technique related to calixarene compounds, for example, it is known to introduce (meth)acryloyl groups into the phenolic hydroxyl groups of p-cresol type or p-tert-butylphenol type calixarene compounds, which are excellent in heat resistance and surface hardness. A technique used for coating (for example, refer to Patent Document 1.); a technique used as a resist material capable of forming a fine pattern (for example, refer to Patent Document 2.) and the like. As mentioned above, the calixarene compound i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C69/732C08F2/48
CPCC07C69/54C07C69/732C07C2603/92C07C43/23C07C69/736C07C233/20C08F2/50C07C69/602C08F2/48C07C59/305
Inventor 山本辰弥门本丰宫本正纪今田知之甲斐英知
Owner DIC CORP
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