JPH0195161A - Indolylazaphthalide compound - Google Patents

Abstract

PURPOSE:To obtain the title compound which forms a clear blue hue with a salicylic acid developer and excelling in the light fastness of a developed color image, by replacing the substituent in position 2 of the indole of an indolylazaphthalide compound by a hydrogen atom. CONSTITUTION:The substituent in position 2 of the indole of an indolylazaphthalide compound such as 3-(4-diethylamino-2-ethoxyphenyl)-3-(1-n- octyl-2-methylindol-3-yl)-4-azaphthalide is replaced by an H atom to obtain an indolylazaphthalide compound of the formula (wherein R1-2 are each an alkyl, R3 is H or an alkyl or aryl, R4 is an alkoxy, X and Y are each H, an alkyl, an alkoxy, a halogen, a nitro, a substituted amino, m is 1-4, and n is 1-3).

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to indolyl azaphthalide compounds. The compounds of the present invention are useful as color formers in pressure-sensitive or heat-sensitive recording materials.

The indolyl azaphthalide compound is
07, Japanese Patent Publication No. 61-4856, etc., as a result of the inventors' studies, it was found that the color hue of the indolyl azaphthalide compound is completely different depending on the type of substituent group or the type of color developer used. did. For example, 3-(4-diethylamino-2-ethoxyphenyl)3-(1-n-octyl-2-methylindol-3-yl)-4-azaphthalide shows blue color development on phenolic resin, but salicylic acid-based color development It shows cyan color development on the agent.

The present inventors investigated various substituents of the indolyl azaphthalide compound, and found that by changing the 2-position of indole to a hydrogen atom, it exhibited a bright blue hue on a salicylic acid-based color developer, and the color image was improved. An indolyl azaphthalide compound with good light resistance was obtained.

Conventionally, crystal violet lactone has been known to exhibit a bright blue hue on a salicylic acid-based color developer, but the light resistance of the colored image is extremely poor.

Therefore, there is a strong desire for a color former that exhibits a bright blue color hue in a blue color recording material and that provides a colored image with good light resistance.

(Structure of the Invention) The present invention provides an indolyl azaphthalide compound represented by the following formula (N).

In the above formula, R,,R, represents an alkyl group, R3 represents a hydrogen atom, an alkyl group, or an aryl group, R4 represents an alkoxy group, X
, Y represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, or a substituted amino group, m represents an integer of 1 to 4, and n represents an integer of 1 to 3.

The aryl group represents a phenyl group, a naphthyl group, or a heteroaromatic ring group, and these include an alkyl group, an alkoxy group, an aryloxy group, a halogen atom, a nitro group, a cyano group, a substituted carbamoyl group, a substituted sulfamoyl group,
The alkyl group may have a substituent such as a substituted amino group, a substituted oxycarbonyl group, or a substituted oxysulfonyl group, and the alkyl group represents a saturated or unsaturated alkyl group or a cycloalkyl group. It may have a substituent such as a group, an aryloxy group, a halogen atom, a cyano group, an acyl group, a hydroxy group, or a sulfuryl group.

Among the substituents represented by R1 or R2 in the above formula, alkyl groups having 1 to 18 carbon atoms are preferred, and these include halogen atoms, alkoxy groups, aryl groups, aryloxy groups, alkyl groups, acyl groups, cyano groups, It may be substituted with a hydroxy group, furfuryl group, etc.

R+ and Rz are more preferably an alkyl group having 2 to 12 carbon atoms.

R1 and Ri are bonded to each other to form a 5- to 8-membered ring, such as piperidine, morpholine, pyrrolidine, piperazine,
A ring such as hexamethyleneimine, caprolactam, or indole may be formed.

〉N is a pyrrolidino group, a piperazino group, a morpholino group, an N-ethylpiperidino group, a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, an N-ethyl-N-isobutylamino group, an N-ethyl-N -isoamylamino/23, N-ethyl-N-benzylamino group, cyamylamino group, diethylamino group,
Examples include a dioctylamino group, an N-ethyl-N-tetrahydrofurfurylamino group, and a diethylamino group.

Among the substituents represented by R1 in the above formula, hydrogen atoms, alkyl groups having 1 to 18 carbon atoms, and aryl groups having 6 to 12 carbon atoms are preferred, and these include halogen atoms, alkoxy groups, aryl groups, and aryloxy groups. group, alkyl group,
It may be substituted with an acyl group, cyano group, hydroxy group, furfuryl group, etc.

R1 is a hydrogen atom, an alkyl group having 2 to 12 carbon atoms,
More preferred are aryl groups having 6 to 12 carbon atoms.

R1 is a hydrogen atom, methyl group, ethyl group, n-butyl group, n-octyl group, 2-ethylhexyl group, n-dodecyl group, n-octadecyl group, benzyl group, p-methylhensyl group, phenethyl group, β- Examples include phenoxyethyl group, β-(4-methoxyphenoxy)ethyl group, phenyl group, and 4-methylphenyl group.

Among the substituents represented by R4 in the above formula, alkoxy groups having 1 to 18 carbon atoms are preferred, and these include halogen atoms, alkoxy groups, aryl groups, aryloxy groups, alkyl groups, acyl groups, cyano groups, and hydroxy groups. , furfuryl group, etc. may be substituted.

More preferably, R4 is an alkoxy group having 2 to 12 carbon atoms.

As R4, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, n-hexyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-dodecyloxy group, n-octadecyl Oxy group, benzyloxy group, p-methylhensyloxy group, phenethyloxy group, β-phenoxyethoxy group, β
-(4-methoxyphenoxy)ethoxy group and the like.

Among the substituents represented by X and Y in the above formula, hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, and 1 to 12 carbon atoms
Preferred are alkoxy groups, chlorine atoms, bromine atoms, nitro groups, mono- or dialkylamine groups having 1 to 12 carbon atoms, and monoacylamino groups having 1 to 12 carbon atoms.

Examples of the present invention are shown below.

Example 1 3-(4-diethylamino-2-ethoxyphenyl)-
3-(1-n-octylindol-3-yl)-4-
Azapthalide quinolinic anhydride 0.2M, 1-n-octylindole 0.2M, acetic acid 100mj! Weigh 0.03M of zinc chloride into a flask equipped with a stirrer, and stir at 30°C for 8 hours. Furthermore, 0.2 M of N,N-diethyl-m-phenetidine and 40 mA of acetic anhydride were added, and the mixture was stirred at 60°C for 3 hours. The reaction mixture is poured into water and made alkaline with an aqueous sodium hydroxide solution. This reaction mixture was subjected to column chromatography using a mixed solvent of n-hexane-acetate (3:1), and the target product was white crystals with a melting point of 111-
Obtained at 2°C. The compound of Example 1 was disclosed in Japanese Patent Application 1986-
259325, a bright blue hue (λwax 585
nm), and the light resistance was also good.

The first step was carried out analogously to Example 1 using the corresponding starting materials.
The compounds shown in the table were obtained.

Claims (1)

[Claims] An indolyl azaphthalide compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) In the above formula, R_1 and R_2 are alkyl groups, R_3 is a hydrogen atom, alkyl group, or aryl group, R_4 is an alkoxy group, and X and Y are hydrogen atoms and alkyl groups. group, alkoxy group,
halogen atom, nitro group or substituted amino group, m is 1
n represents an integer from 1 to 3.