Anthrapyridone compounds, water-based magenta ink...

Compositions: coating or plastic – Coating or plastic compositions – Marking

Reexamination Certificate

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C546S076000

Reexamination Certificate

active

06645283

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel anthrapyridone compound, a water-based magenta ink composition, and a method of ink-jet recording.
BACKGROUND ART
Diverse ink jetting processes have been developed for the recording method by means of ink-jet printer, and any process comprises generating ink droplets to deposit them onto various recording materials (such as paper, film, cloth) for recording. The recording method by means of ink-jet printer has rapidly been spread in recent years and will be propagated in future because the method brings about no noise due to the system in which a recording head does not contact with the recording material and because the method advantageously allows the printer to become downsized, to work in a high-speed and to give color printing, easily. For recording an image information or a character information pictured on a computer color display in color by means of an ink-jet printer, the information is generally printed according to subtractive color mixing of inks of four colors, namely yellow(Y), magenta(M), cyan(C) and black(K). In order to print reproductively an image pictured by additive color mixing of R(red), G(green), B(blue) on a CRT display as faithfully as possible according to subtractive color mixing, the dyestuffs used, especially ones for a YMC ink, are desired to have color hues close to the respective standards of YMC (“Japan Color Standard Paper” published by Japan Printing Machinery Manufacturers Association) and vividness. Additionally, it is required that the resulting ink composition is stable for long-term storage and that the resulting printed image is of a high optical density and has excellent fastness including water fastness and light fastness.
Ink-jet printers are increasingly used in a wide range from a small one for OA use to a big one for industrial use. So, excellence in fastness such as water fastness and light fastness of the printed image is more strictly demanded. The water fastness is substantially improved by coating inorganic micro particles such as porous silica, cationic polymer, alumina sol, special ceramic which can absorb dyestuff from ink, on a paper sheet together with PVA resin. Various coated sheets for ink-jet printing are already available on the market. But light fastness is not yet improved by any established technique. Of tetrachromatic colors of YMCK, magenta especially has many dyestuffs which are naturally weak in light fastness, and the improvement is an important problem to be solved.
The typical types of chemical structure of magenta dyestuffs used in a water-soluble ink for ink-jet recording are a xanthene type disclosed by JP Laid-Open No.89811/1979, JP Laid-Open No.60053/1996 and JP Laid-Open No.143798/1996 etc., or an azo type using the H acid disclosed by JP Laid-Open No.62562/1986, JP Laid-Open No.156168/1987, JP Laid-Open No.203970/1991, JP Laid-Open No.157698/1995 and JP Publication No.78190/1995 etc. The xanthene type is indeed excellent in hue and vividness, but is inferior in light fastness. The azo type using the H acid is good in hue and water fastness, but is inferior in light fastness and vividness. As disclosed by JP Laid-Open No.203970/1991, for example, some magenta dyestuffs in this type being excellent in vividness and light fastness have been developed, but are still inferior in light fastness to dyestuffs having other hue such as, typically, yellow dyestuffs and cyan dyestuffs which are copper phthalocyanine type.
Furthermore, for a chemical structure of magenta dyes excellent in vividness and light fastness, an anthrapyridone type is known as disclosed by JP Laid-Open No.74173/1984 and JP Laid-Open No.16171/1990, but can not yet show any satisfactory properties in hue, vividness, light fastness, water fastness and stability in solution.
An object of the present invention is to provide a magenta dye which has hue and vividness suitable for ink-jet recording and supplies the recorded material with a high fastness in light fastness and water fastness.
DISCLOSURE OF THE INVENTION
The present inventors made a diligent study to solve the above problem and, as a result, have completed the present invention. Namely, the present invention is as follows:
A novel anthrapyridone compound represented by Formula (1) as described below or the salt thereof
(wherein, R
1
is hydrogen, an alkyl group, a hydroxy lower alkyl group, cyclohexyl, a mono- or di-alkylaminoalkyl group, or a cyano lower alkyl group; R
2
is hydrogen, methyl, ethyl, phenoxy (which may be substituted), sulfo or carboxy; X and Y represent independently chloro, hydroxy, an alkoxy group, phenoxy (which may be substituted with the substituents selected from the group consisting of sulfo, carboxy, acetylamino, amino, and hydroxy), a mono- or di-alkylamino group having sulfo or carboxy, anilino (which may be substituted with one or two substituents selected from the group consisting of sulfo and carboxy), naphthylamino (the naphthyl may be substituted with sulfo), or a mono- or di-alkylaminoalkylamino group, except that X and Y are respectively any groups selected from chloro, hydroxy and anilino (which may be substituted with one or two substituents selected from the group consisting of sulfo and carboxy) if R
2
is hydrogen.)
[2] A novel anthrapyridone compound or the salt thereof according to the above [1], wherein said compound is represented by Formula (2) as described below:
(wherein, R
1
is hydrogen or an alkyl group; X and Y represent independently chloro, hydroxy, an alkoxy group, phenoxy (which may be substituted with the substituents selected from the group consisting of sulfo, carboxy, acetylamino, amino, and hydroxy), an alkylamino group having sulfo or carboxy, anilino (which may be substituted with one or two substituents selected from the group consisting of sulfo and carboxy), naphthylamino (the naphthyl may be substituted with sulfo), or a dialkylaminoalkylamino group, except that X and Y are respectively any groups selected from choloro, hydroxy, and anilino (which may be substituted with one or two substituents selected from the group consisting of sulfo and carboxy).)
[3] A novel anthrapyridone compound or the salt thereof according to the above [1] or [2], wherein X is anilino (which may be substituted with one or two substituents selected from the group consisting of sulfo and carboxy) or naphthylamino (the naphthyl may be substituted with sulfo); and Y is chloro, hydroxy, an alkoxy group, phenoxy (which may be substituted with the substituents selected from the group consisting of sulfo, carboxy, acetylamino, amino, and hydroxy), anilino (which may be substituted with one or two substituents selected from the group consisting of sulfo and carboxy), an alkylamino group having sulfo or carboxy, or a dialkylaminoalkylamino group.
[4] A novel anthrapyridone compound or the salt thereof according to the above [1] or [2], wherein R
1
is hydrogen or methyl; X is anilino substituted with one or two substituents selected from sulfo and carboxy; and Y is hydroxy, methoxy, phenoxy (which may be substituted with the substituents selected from the group consisting of sulfo, carboxy, acetylamino, amino, and hydroxy), anilino having sulfo, an alkylamino group having sulfo or carboxy, or a dialkylaminoalkylamino group.
[5] A novel anthrapyridone compound or the salt thereof according to the above [1] or [2], wherein X is naphthylamino substituted with sulfo; and Y is chloro, hydroxy, methoxy, phenoxy (which maybe substituted with the substituents selected from the group consisting of sulfo, carboxy, acetylamino, amino, and hydroxy), or an alkylamino group having sulfo or carboxy.
[6] A novel anthrapyridone compound or the salt thereof according to the above [1] or [2], wherein R
1
is hydrogen or methyl; X is naphthylamino substituted with three sulfo groups; and Y is chloro, hydroxy, or phenoxy.
[7] A novel anthrapyridone compound or

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