JP2727387B2 - Diphenyl ether derivative - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION The present invention relates to a recording material using an electron-donating colorless dye and an electron accepting compound, for example, an electron accepting compound useful for pressure-sensitive recording materials and heat-sensitive recording materials, or a polymer material. It relates to a diphenyl ether derivative useful as one.

[0002]

2. Description of the Related Art Various phenolic compounds are known as electron-accepting compounds for pressure-sensitive recording materials and heat-sensitive recording materials. All of them are known as color density, color sensitivity, unprinted area preservability, and printed area preservation ( Weather resistance, chemical resistance, etc.). For example, when 4-isopropoxy-4'-hydroxydiphenylsulfone disclosed in Japanese Patent Publication No. 3-54555 is used for thermal recording paper, it exhibits high color density and sensitivity, but is written with a magic marker, highlighter, or the like. As a result, the unprinted portion was colored or the printed image disappeared, and the chemical resistance was insufficient.

When bis- (3-phenyl-4-hydroxyphenyl) sulfone disclosed in JP-A-2-266981 is used for heat-sensitive recording paper, the color-forming sensitivity is low, and it is difficult to write with a magic pen or a fluorescent pen. Although no decoloration of the image was shown, the unprinted portion was colored, and if hand cream or the like was attached, the image was immediately decolored, and the color sensitivity and chemical resistance were insufficient.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a color density,
An object of the present invention is to provide a phenolic compound which simultaneously satisfies the color development sensitivity, preservability of an unprinted portion, preservability of a printed portion (weather resistance, chemical resistance, etc.).

[0005]

The above object has been achieved by developing a diphenyl ether derivative represented by the following general formula (1) as a phenolic compound. General formula (1)

[0006]

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X represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an allyl group, or an aryl group, respectively.

The group represented by X is preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, an allyl group, or an aryl group having 6 to 10 carbon atoms. Is preferably a hydrogen atom, chlorine atom, bromine atom, methyl group, ethyl group, normal propyl group, isopropyl group, secondary butyl group, tertiary butyl group, benzyl group, allyl group, phenyl group, α-phenylallyl group. The substitution position of X is preferably the ortho position of the hydroxy group.

Specific examples of the compound represented by the general formula (1) are shown below, but the present invention is not limited thereto. The following compounds may have water of crystallization.

[0010]

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[0011]

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The melting point of the compound of the present invention can be controlled by including water or an organic solvent in the crystal. The compound of the present invention can be synthesized with reference to known synthesis methods. For example, 4-chlorosulfonyldiphenyl ether and chlorobenzene are mixed with -10 in the absence of a solvent or in a solvent such as dichloromethane, dichloroethane, nitrobenzene, chlorobenzene, and carbon disulfide in the presence of a binder such as aluminum chloride, iron chloride, zinc chloride, and sulfuric acid. The reaction is carried out at a reaction temperature of ~ 150 ° C for 0.5 to 24 hours, usually treated with ice-cooled hydrochloric acid, and if necessary, purified by recrystallization, silica gel column chromatography or the like, and then alkali-hydrolyzed to obtain the desired compound. Obtainable.

[0013]

【Example】

Example 1 Synthesis of water bimolecular adduct of the compound of specific example (1) In 30 ml of chlorobenzene, 18.4 g of 4-chlorosulfonyldiphenyl ether and 1.2 g of ferric chloride were added, and the mixture was stirred at 130 ° C for 24 hours. After cooling, 20 ml of dimethyl sulfoxide was added, and chlorobenzene was distilled off at 170 ° C. After cooling, pour the reaction mixture into water and add bis-
Crude crystals of [4- (4-chlorophenylsulfonyl) phenyl] ether were obtained. This material was recrystallized from dimethylformamide to give white crystals of bis- [4- (4-chlorophenylsulfonyl) phenyl] ether. Then, after hydrolysis according to a conventional method, recrystallization from dilute acetic acid gave a bimolecular adduct of crystal water of the compound of the specific example (1). Melting point 100-102 ° C

Example 2 Preparation of a glassy substance of the compound of Example (1) The compound obtained in Example (1) was heated to 130 ° C. to remove water of crystallization, and then cooled to room temperature. Became material. Although this substance did not show a melting point, it was confirmed from the following spectrum data that it was the compound of Specific Example (1).

¹ H-NMR (400 MHz, Aceto
n / TMS) data 9.45 ppm (s, 2H), 7.92 ppm (d, 4
H), 7.78 ppm (d, 4H), 7.28 ppm
(D, 4H), 6.95 ppm (d, 4H) MS (m / e) data 482 (M +), 417, 373, 342, 326, 2
8

Claims (1)

(57) [Claims] 1. A diphenyl ether derivative represented by the following general formula (1). General formula (1) X represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an allyl group, or an aryl group, respectively.