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Novel bis(4-hydroxyphenyl) cyclohexene

A technology of hydroxyphenyl and cyclohexene, which is applied in the field of new bicyclohexenes, can solve problems such as insufficient solubility, and achieve the effect of low melting point and excellent solvent solubility

Active Publication Date: 2014-12-10
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, any of such compounds have insufficient solubility in solvents and require improvement.

Method used

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  • Novel bis(4-hydroxyphenyl) cyclohexene
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  • Novel bis(4-hydroxyphenyl) cyclohexene

Examples

Experimental program
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Effect test

Embodiment 1

[0133] [Synthesis of a mixture of 1,3-bis(4-hydroxyphenyl)-1-cyclohexene and 1,5-bis(4-hydroxyphenyl)-1-cyclohexene]

[0134]18.0 g (49.9 mmoles) of 1,1,3-tris(4-hydroxyphenyl)cyclohexane obtained in Reference Example 1, four Ethylene glycol 9.0g, 16% sodium hydroxide aqueous solution 1.3g (5.0mmol), while decompressing to 10kPa, heat up to 170°C under stirring, and then distill off the phenol generated under reduced pressure while stirring. The decomposition reaction was further carried out at this temperature for 9 hours.

[0135] After the reaction was completed, acetic acid was added after cooling to 100° C. for neutralization. After adding methyl isobutyl ketone and water and stirring, the aqueous layer was separated. The water washing operation which added water to the obtained oil layer, stirred, and separated the water layer was implemented 3 times. Thereafter, after distilling and removing the solvent from the oil layer washed with water, 18 g of toluene was added,...

reference example 2

[0144] [Synthesis of 1,1,3-tris(4-hydroxy-3-methylphenyl)cyclohexane]

[0145] Put 1513.4 g of orthocresol, 73 g of 35% hydrochloric acid, 14.2 g of dodecyl mercaptan, and 134.4 g of methanol into a four-necked flask with a capacity of 3 liters, and keep the liquid temperature at 30 °C under a nitrogen atmosphere. 134.5 g of 2-cyclohexen-1-one was added dropwise over 3.5 hours at ~32°C, and after the dropwise addition was completed, it was stirred at 30°C to 32°C for 22 hours. After completion of the reaction, an aqueous sodium hydroxide solution was added to neutralize, and then the temperature was raised to distill off methanol. Thereafter, methyl isobutyl ketone and water were added to the oil layer obtained by separating and removing the water layer, stirred, washed with water, and the water layer was separated and removed. From the obtained oil layer, o-cresol which had not reacted with methyl isobutyl ketone was distilled off under reduced pressure, and removed. The re...

Embodiment 2

[0147] [1,3-bis(3-methyl-4-hydroxyphenyl)-1-cyclohexene and 1,5-bis(3-methyl-4-hydroxyphenyl)-1-cyclohexene mixture synthesis]

[0148] The crystallization of the addition compound of 1,1,3-tris(4-hydroxy-3-methylphenyl)cyclohexane obtained in Reference Example 2 was placed in a four-necked flask equipped with a thermometer, a cooler and stirring wings 236.8g, 50.3g of tetraethylene glycol, 12.5g of 16% sodium hydroxide aqueous solution, after raising the liquid temperature to 190°C, carry out the decomposition reaction for 2 hours while distilling o-cresol out of the reaction system under reduced pressure . After completion of the reaction, neutralize with acetic acid, add methyl isobutyl ketone and water and stir, then separate and remove the water layer. Methyl isobutyl ketone was distilled off from the obtained oil layer to obtain 1,3-bis(3-methyl-4-hydroxyphenyl)-1-cyclohexene with a purity of 86.8% (high performance liquid chromatography) (C) and 132.3 g of a mixture ...

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Abstract

In order to provide a novel bis(4-hydroxyphenyl) cyclohexene with excellent reactivity and solubility in solvents, the present invention provides the bis(4-hydroxyphenyl) cyclohexene represented in general formula (1). (In the formula, R1 and R2 are each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a phenyl group, a phenyloxy group, a hydroxyl group or a halogen atom, R3 is an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a phenyl group, a phenyloxy group, or a halogen atom, and n and m are independently integers from 0 to 4; if n is 2 or greater, the R1's may be the same or different; if m is greater than or equal to 2, R2's may be the same or different; k indicates an integer from 0 to 7; R3 in general formula (1) is not substituted by a carbon atom bonded to a 4-hydroxyphenyl group, and if k is greater than or equal to 2, the R3's may be the same or different, and the bonding position of a hydroxyphenyl group optionally substituted by an R2 is position 3 or 5 of the cyclohexene ring.

Description

technical field [0001] The present invention relates to novel bis(4-hydroxyphenyl)cyclohexenes. In further detail, the present invention relates to a novel bis(4- hydroxyphenyl)cyclohexenes. Background technique [0002] Conventionally, polyphenols have been used in various fields as raw materials for thermoplastic synthetic resins such as polycarbonate resins, thermosetting resins such as epoxy resins, and photosensitive materials such as photoresists for semiconductors. [0003] In recent years, the performance required for raw material polyphenols has been further advanced and densified along with the increasing demand for improvement of various performances in the above application fields. As one of such demands for performance improvement, there is a need for polyphenols that are excellent in solubility and reactivity in solvents when polyphenols are used as raw materials for various compositions and resins, and are used as compositions, When used as a resin, it has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/23
CPCC07C39/23C07D303/30C07C39/17C07C2101/12C07C2601/12
Inventor 芦田一仁桥本祐树山本智也
Owner HONSHU CHEM INDAL