Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2000-02-29
2002-05-07
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
Reexamination Certificate
active
06383276
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an azomethine compound. In detail, the invention relates to an azomethine compound suitable for a jet printing ink of magenta color.
BACKGROUND OF THE INVENTION
In an ink-jet recording method, images or characters are printed on image-receiving material with ink ejected from very fine nozzles. The ink-jet recording method can be conducted by using a relatively inexpensive apparatus (i.e., an ink-jet printer), as compared with other printing methods. Further, in proportion to improvement of the method, images of high qualities have been given recently. Now, the ink-jet recording method is one of the most popular image-recording methods.
Ink for the ink-jet recording method (i.e., jet printing ink) must not choke the fine nozzles. Since aqueous inks (aqueous solutions of dyes) hardly choke the nozzles, they are widely used. However, the aqueous inks have poor water resistance. Various means (described in Japanese Patent Provisional Publication Nos. 4(1992)-28776, 4(1992)-189876, 4(1992)-261478, 4(1992)-359071 and 4(1992)-359072) have been proposed to improve the water resistance of the aqueous inks or water-soluble dyes. in addition, the water-soluble dyes have poor light resistance.
Oil-soluble dyes (described in Japanese Patent Provisional Publication Nos. 1(1989)-170672, 3(1991)-221137, 7(1995)-96163, 8(1996)-218015, 9(1997)-3376, 9(1997)-241565, 9(1997)-286939 and 10(1998)-279873) have been proposed in place of the water-soluble dyes. The oil-soluble dyes are usually incorporated in microcapsules or soaked in polymers when they are used for ink-jet printing. Although the oil-soluble dyes have satisfying water resistance, they are unsatisfactory in color reproduction and color stability.
SUMMARY OF THE INVENTION
Water-soluble dyes for ink-jet recording have poor resistance against water and light, while oil-soluble dyes are unsatisfactory in color reproduction and color stability.
An object of the present invention is to provide an oil-soluble dye excellent in color reproduction and color stability.
Another object of the invention is to provide an azomethine compound suitable for a jet printing ink of magenta color.
A further object of the invention is to provide an oily magenta ink for ink-jet recording.
The applicants.have found an azomethine compound having light-absorption characteristics suitable for a magenta dye. The compound is oil-soluble, and is advantageously used in a preparation of an oily magenta ink for ink-jet recording.
The present invention provides an azomethine compound represented by the formula (I):
wherein
R
1
is an alkyl group having 1 to 16 carbon atoms; R
2
is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano; R
3
is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group having 3 to 30 carbon atoms; R
4
is an alkyl group having 1 to 16 carbon atoms; L
1
is an alkylene group having 1 to 30 carbon atoms or an arylene group having 6 to 30 carbon atoms; L
2
is —CO—NH—, —SO
2
—NH—, —O—, —O—CO— or —O—CO—NH—; X is cyano, an alkoxycarbonyl group having 2 to 19 carbon atoms, an alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon atoms or an arylsulfamoyl group having 6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms; m is 1, 2, 3 or 4; n is an integer of 1 to 18; p is 0, 1, 2, 3 or 4; and R
1
, L
1
, L
2
, R
3
and R
4
have 20 to 50 carbon atoms in total.
The invention also provides an oily magenta ink in which an azomethine dye represented by the formula (I) is dissolved in an organic solvent.
The azomethine compound represented by the formula (I)has excellent characteristics suitable for a magenta dye. Accordingly, the azomethine compound can be advantageously used in a preparation of an oily magenta ink for ink-jet recording.
Further, the azomethine compound represented by the formula (I) is excellent in stability to light and heat. Accordingly, the azomethine compound can be used a magenta dye that is excellent in a light resistance and in a heat resistance.
DETAILED DESCRIPTION OF THE INVENTION
The azomethine compound represented by the formula (I) can be classified into the three embodiments represented by the formulas (Ia), (Ib) and (Ic), respectively. The embodiment of the formula (Ia) is particularly preferred.
In the formulas (Ia) to (Ic), R
1
is an alkyl group having 1 to 16 carbon atoms. The alkyl group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 6 carbon atoms, and most preferably has 1 to 4 carbon atoms. The alkyl group can have a branched chain. Examples of the alkyl groups include methyl and t-butyl.
In the formulas (Ia) to (Ic), R
2
is a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or cyano.
The alkyl group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 4 carbon atoms, and most preferably has 1 or 2 carbon atoms. The alkyl group can have a branched chain. Examples of the alkyl groups include methyl and ethyl.
The alkoxy group preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, further preferably has 1 to 4 carbon atoms, and most preferably has 1 or 2 carbon atoms. The alkoxy group can have a branched chain. Examples of the alkoxy groups include methoxy.
The amido group preferably has 2 to 12 carbon atoms, more preferably has 2 to 8 carbon atoms, further preferably has 2 to 6 carbon atoms, and most preferably has 3 or 4 carbon atoms. Examples of the amido groups include acetamido.
The alkoxycarbonylamino group preferably has 2 to 12 carbon atoms, more preferably has 2 to 8 carbon atoms, further preferably has 2 to 6 carbon atoms, and most preferably has 2 or 3 carbon atoms. Examples of the alkoxycarbonylamino groups include methoxycarbonylamino.
In the formulas (Ia) to (Ic), R
3
is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an alkoxylcarbonylalkyl group having 3 to 30 carbon atoms.
The alkyl group preferably has 2 to 25, more preferably has 3 to 20 carbon atoms, and most preferably has 4 to 16 carbon atoms. The alkyl group can have a branched chain.
Examples of the aryl groups include phenyl and naphthyl. Phenyl is preferred. The aryl group can have a substituent group. Examples of the substituent groups include a halogen atom, an alkyl group having 1 to 24 carbon atoms and an alkoxy group having 1 to 24 carbon atoms. The aryl group has 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 16 carbon atoms. The number of the carbon atoms means the number of the total carbon atoms contained in the aryl group and the substituent group.
The alkyl moiety of the aryloxyalkyl group can have a branched chain. The aryl moiety of the aryloxyalkyl group is preferably phenyl. The aryloxyalkyl group can have a substituent group. Examples of the substituent groups include a halogen atom, an alkyl group having 1 to 23 carbon atoms and an alkoxy group having 1 to 23 carbon atoms. The aryloxyalkyl group has 7 to 30 carbon atoms, preferably has 7 to 25 carbon atoms, more preferably 7 to 20 carbon atoms, and further preferably 7 to 16 carbon atoms. The number of the carbon atoms means the number of the total carbon atoms contained in the aryloxyalkyl group and the substituent group.
The alkoxycarb
Asanuma Naoki
Mikoshiba Hisashi
Motoki Masuji
Sato Tadahisa
Suzuki Ryo
Fuji Photo Film Co. , Ltd.
Klemanski Helene
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