TETRAALKYL-SUBSTITUTED NITROGEN-CONTAINING HETERO...

Details TETRAALKYL-SUBSTITUTED NITROGEN-CONTAINING HETERO... TETRAALKYL-SUBSTITUTED NITROGEN-CONTAINING HETERO...

2000-04-17

2002-09-03

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C534S751000, C534S752000, C534S799000, C534S800000

Reexamination Certificate

active

06444020

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a 2,2,6,6-tetraalkyl-substituted nitrogen-containing hetero ring-bonded azo dye-having high fastness to light, heat, air and chemicals. Further, the invention relates to an ink-jet recording method and, more particularly, to ink-jet ink for formation of images having excellent hue and high fastness to light, heat, air, water and chemicals, and to an ink-jet recording method using such ink. Furthermore, the invention is concerned with a thermal transfer recording material for recording images by the heating corresponding to image information.
BACKGROUND OF THE INVENTION
Various requisites, including high solubilities in solvents, capability for high-density recording, good hue, high fastness to light, heat, air, water and chemicals, such high fixability to image-receiving materials as to make the ink bleeding, excellent keeping quality as the ink, no toxicity high purity and availableness at a low price, are requisites of a coloring matter for ink-jet ink. However, it is very difficult to select a coloring matter satisfying those requirements at a high level. In particular, it is intensely desired for the coloring matter to have excellent fastness to light.
From the aforementioned viewpoints, various dyes and pigments for ink-jet ink have been proposed and examined. However, none of known coloring matters is a coloring matter meeting all the foregoing requirements. For instance, both hue requirement and fastness requirement are difficult to simultaneously fulfill by the use of known dyes and pigments having C.I. numbers.
SUMMARY OF THE INVENTION
An object of the invention is to provide an azo dye having excellent spectral characteristics and high fastness to light, heat, air and chemicals.
Another object of the invention is to obtain ink-jet ink and an ink-jet recording method suitable for forming images of high fastness.
Still another object of the invention is to provide a thermal transfer dye donating material comprising an azo dye having high stability to light, heat, air and chemicals.
As a result of our intensive studies, the azo dyes represented by the following formula (I) have been discovered, and it has been found that these azo dyes enabled effective attainment of the aforementioned objects to provide highly fast images and to overcome the defects of prior arts.
More specifically, the foregoing objects are achieved by the following embodiments (1) to (5) of the invention:
(1) An azo dye represented by the following formula (I);
wherein Z represents an atomic group which forms, together with a nitrogen atom, a five-, six- or seven-membered ring, R
1
represents a hydrogen atom, an oxy radical, an aliphatic group, an aliphatic oxy group, an acyl group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group or an acyloxy group, R
2
, R
3
, R
4
and R
5
, which may be the same or different, each represents an alkyl group, or R
2
and R
3
and/or R
4
and R
5
may be combined with each other to form a ring, and Dye represents a dye moiety group necessary for forming an azo dye.
(2) An azo dye as described in Embodiment (1), which dye is represented by the following formula (Ia)
wherein R
1
and Dye denote the same meanings as those defined for formula (I).
(3) Ink-jet ink comprising an azo dye represented by the above formula (I). Further, the azo dye represented by the above formula (
1
a
) is more preferred.
(4) An ink-jet recording method which comprises jetting ink as oil droplets to record images on an image-receiving material, said ink being ink as described in Embodiment (3).
(5) A thermal transfer recording material comprising a thermal transfer dye donating material and a thermal transfer image-receiving material, said dye donating material containing at least one azo dye represented by the formula (I) defined in Embodiment (1). Further, the azo dye represented by the formula (I) is preferably represented by the formula (Ia).
DETAILED DESCRIPTION OF THE INVENTION
When the groups relating to the invention contain an aliphatic moiety, the aliphatic moiety may be a saturated or unsaturated one having a straight-chain, branched or cyclic form, with examples including alkyl, alkenyl, cycloalkyl and cycloalkenyl groups. These groups each may have no substituent group or at least one substituent group. in another case where the groups relating to the invention contain an aryl moiety, the aryl moiety may be a single ring or a condensed ring, which may have no substituent group or at least one substituent group. In the other case where the groups relating to the invention contain a heterocyclic moiety, the heterocyclic moiety has at least one hetero atom (e.g., nitrogen, sulfur and oxygen) in the ring, and the ring may be a saturated or unsaturated ring which may be a single or condensed ring having no or at least one substituent group.
The term “substituent group” as used in the invention describes all groups which can be substituted for hydrogen atoms, with examples including an aliphatic group, an aryl group, a heterocyclic group, an acyl group, an acyloxy group, an acylamino group, an aliphatic oxy group, an aryloxy group, a heterocyclic oxy group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, a heterocyclic oxycarbonyl group, a carbamoyl group, an aliphatic sulfonyl group, an arylsulfonyl group, a heterocyclic sulfonyl group, an aliphatic sulfonyloxy group, an arylsulfonyloxy group, a heterocyclic sulfonyloxy group, a sulfamoyl group, an aliphatic sulfonamido group, an arylsulfonamido group, a heterocyclic sulfonamido group, an aliphatic amino group, an arylamino group, a heterocyclic amino group, an aliphatic oxycarbonylamino group, an aryloxycarbonylamino group, a heterocyclic oxycarbonylamino group, an aliphatic sulfinyl group, an arylsulfinyl group, an aliphatic thio group, an arylthio group, a hydroxy group, a cyano group, a sulfo group, a carboxyl group, an aliphatic oxyamino group, an aryloxyamino group, a carbamoylamino group, a sulfamoylamino group, a halogen atom, a sulfamoylcarbamoyl group, a carbamoylsulfamoyl group, a dialiphatic oxyphosphinyl group and a diaryloxyphosphinyl group.
In formula (I), Z represents an atomic group which forms, together with a nitrogen atom, a five-, six- or seven-membered ring, preferably a five- or six-membered ring, and more . preferably a six-membered ring. Examples of the five-, six- or seven-membered rings include a piperidine ring and a pyrrolidine ring, and a piperidine ring being preferred. Further, these rings may have a substituent group other than the groups represented by R
2
to R
5
, such as the groups shown in the above-described examples of the “substituent groups” as used in the invention.
R
1
in formula (I) represents a hydrogen atom; an oxy radical; an aliphatic group, preferably an unsubstituted or substituted alkyl group containing at most 10 carbon atoms, such as methyl, ethyl or 2-methanesulfonamidoethyl group, or an unsubstituted or substituted alkenyl group containing at most 10 carbon atoms, such as allyl or vinyl group; an aliphatic oxy group, preferably an unsubstituted or substituted alkoxy group containing at most 10 carbon atoms, such as methoxy, ethoxy or 2-methoxyethoxy group, or an unsubstituted or substituted alkenyloxy group containing at most 10 carbon atoms, such as allyloxy group; an acyl group, preferably an unsubstituted or substituted alkylcarbonyl group containing at most 10 carbon atoms, such as acetyl or propionyl group, or an unsubstituted or substituted alkenylcarbonyl group containing at most 10 carbon atoms, such as acryloyl or methacryloyl group; an unsubstituted or substituted arylcarbonyl group containing at most 10 carbon atoms,. such as benzoyl group; an aliphatic oxycarbonyl group, preferably an unsubstituted or substituted alkoxycarbonyl group containing at most 10 carbon atoms, such as methoxycarbonyl or ethoxycarbonyl group, or an unsubstituted or substituted alkenyloxycarbonyl group containing at most 10 carbon atoms, such as allyloxycarbonyl group; an aryloxycarbonyl group, preferably an unsubs

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