Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
1999-11-22
2002-06-25
Kelly, Cynthia H. (Department: 1774)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C438S195000, C534S676000, C534S678000, C534S679000, C534S680000, C534S681000, C534S810000
Reexamination Certificate
active
06409810
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to new water-soluble trisazo compounds and colored articles therefrom.
PRIOR ARTS
Among various color recording methods, one typical method is the recording method by means of ink jet printers wherein ink droplets are produced and deposit on various materials to be recorded such as papers, films and fabrics so that recordings are effected. This method has advantages that it is silent since materials to be recorded are not contacted with a recording head and that miniaturization, speeding up and color printing can be easily achieved. Thus, it has recently come into wide use and it is expected to greatly spread in future.
As inks for pens, felt-tip pens and the like as well as inks for ink jet printers, aqueous inks comprising water-soluble dyes dissolved in aqueous media are used. Generally, the aqueous inks comprise water-soluble organic solvents in order to prevent the inks from clogging in nibs and ink delivery nozzles. These inks should meet the requirements that they can form images having a high optical density, that they do not clog nibs and ink delivery nozzles, that they are easily dried on materials to be recorded, that they hardly blot and that they have excellent storage stability. In addition, images therefrom should have sufficient light and water resistances.
Various inks having different hues are prepared from various dyes. Among the inks, black inks are important since they are used in mono-color and full-color images. As dyes for black inks, many dyes have been proposed as described in prior patent applications, for example, JP-55144067A(1980), JP-57207660A(1982), JP-58147470(1983), JP-59093766A(1984), JP-62190269A(1987), JP-62246975A(1987), JP-63022867A(1988), JP-63033484A(1988), JP-01093389A(1989), JP-02140270A(1990), JP-03167270A(1991), JP-03200852A(1991), JP-04359065A(1992), JP-06172668A(1994), JP-06248212A(1994), JP-07026160A(1995), JP-07268256A(1995) and the like. However, the prior dyes cannot satisfy the commercial requirements as described above.
BACKGROUND OF THE INVENTION
An object of the present invention is to provide a black recording fluid having a high solubility, stable even after a long storage, capable of forming a printed image with a high optical density and excellent in water and light resistances.
SUMMARY OF THE INVENTION
The present inventors have earnestly investigated in order to solve the aforementioned problem, achieving the present invention.
Accordingly, the present invention relates to:
(1) a trisazo compound represented by the following general formula (1):
wherein
D is an 8-hydroxy-1-naphthyl group substituted with one or two sulfo groups;
A is a group of the general formula (2) or (3):
wherein R
1
and R
2
are each independently hydrogen, amino, hydroxyl, carboxyl, sulfo, phosphono, (C1-C4)alkoxycarbonyl, (C1-C4)alkyl optionally substituted with hydroxy or (C1-C4)alkoxy, (C1-C4)alkoxy optionally substituted with hydroxy or (C1-C4)alkoxy, (C2-C4)alkanoylamino optionally substituted with hydroxy or (C1-C4)alkoxy or ureido, R
3
is hydrogen, (C1-C4)alkyl or (C1-C4)alkoxy, and R
4
is hydrogen, sulfo or phosphono;
B is a group represented by the general formula (4):
wherein R
5
, R
6
and R
7
are each independently hydrogen, hydroxyl, amino, carboxyl, (C1-C4)alkoxy, (C1-C4)alkoxycarbonyl, (C1-C4)alkyl, mono- or bis-carboxy-(C1-C3)alkylamino, carboxy-(C1-C3)alkoxy, (C1-C4)alkylamino optionally substituted with hydroxy or (C1-C4)alkoxy, (C1-C4)alkanoylamino, sulfo, halogen or ureido; and
m is 0 or 1,
or its salt;
(2) a salt of a trisazo compound as defined in (1) wherein the salt is a lithium salt, a sodium salt, or an ammonium salt represented by the general formula (5):
wherein R
8
to R
11
are each independently hydrogen, (C1-C4)alkyl, hydroxy-(C1-C4)alkyl or hydroxyethoxy-(C1-C4)alkyl group;
(3) a trisazo compound or its salt as defined in (1) or (2) wherein D is
8-hydroxy-3,6-disulfo-1-naphthyl,
8-hydroxy-4,6-disulfo-1-naphthyl,
8-hydroxy-2,4-disulfo-1-naphthyl,
8-hydroxy-3,5-disulfo-1-naphthyl,
8-hydroxy-4,7-disulfo-1-naphthyl,
8-hydroxy-5,7-disulfo-1-naphthyl,
8-hydroxy-4-sulfo-1-naphthyl,
8-hydroxy-5-sulfo-1-naphthyl, or
8-hydroxy-6-sulfo-1-naphthyl;
(4) a trisazo compound or its salt as defined in any one of (1) to (3) wherein A is the group of the general formula (2) wherein R
1
and R
2
are each independently hydrogen, methyl, ethyl, methoxy, ethoxy, methoxyethoxy, amino, hydroxyl, carboxyl, sulfo, acetylamino, n-propionylamino or ureido, or the general formula (3) wherein R
3
is hydrogen, methyl or methoxy and R
4
is hydrogen or sulfo;
(5) a trisazo compound or its salt as defined in any one of (1) to (4) wherein A is the group of the general formula (2) wherein R
1
is methyl, methoxy or methoxyethoxy and R
2
is hydrogen, methyl, methoxy, amino, hydroxyl, acetylamino or ureido;
(6) a trisazo compound or its salt as defined in any one of (1) to (4) wherein A is the group of the general formula (3) wherein R
3
is hydrogen or methoxy and R
4
is hydrogen or sulfo;
(7) a trisazo compound or its salt as defined in any one of (1) to (6) wherein B is the group of the general formula (4) wherein R
5
is hydrogen, methyl, methoxy, chlorine, carboxyl or sulfo, and R
6
and R
7
are each independently hydroxyl, amino, carboxymethylamino, carboxymethoxy, acetylamino or ureido;
(8) a trisazo compound or its salt as defined in any one of (1) to (7) wherein m is zero;
(9) an aqueous ink composition containing a trisazo compound or its salt as defined in any one of (1) to (8);
(10) an article colored with a trisazo compound as defined in any one of (1) to (8) or an aqueous ink composition as defined in (9); and
(11) a colored article as defined in (10) wherein coloring is effected by means of a printer.
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be fully explained below.
In the compound represented by the aforementioned formula (1), D is an 8-hydroxy-1-naphthyl group substituted with one or two sulfo groups. Preferably, it includes 8-hydroxy-3,6-disulfo-1-naphthyl, 8-hydroxy-4,6-disulfo-1-naphthyl, 8-hydroxy-2,4-disulfo-1-naphthyl, 8-hydroxy-3,5-disulfo-1-naphthyl, 8-hydroxy-4,7-disulfo-1-naphthyl, 8-hydroxy-5,7-disulfo-1-naphthyl, 8-hydroxy-4-sulfo-1-naphthyl, 8-hydroxy-5-sulfo-1-naphthyl, 8-hydroxy-6-sulfo-1-naphthyl and the like. 8-Hydroxy-3,6-disulfo-1-naphthyl, 8-hydroxy-4,6-disulfo-1-naphthyl, 8-hydroxy-2,4-disulfo-1-naphthyl, 8-hydroxy-4-sulfo-1-naphthyl or the like is more preferable.
In A and B in the aforementioned formula (1), examples of (C1-C4)alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or the like, preferably methyl or ethyl. Examples of (C1-C4) alkyl group substituted with hydroxy or (C1-C4)alkoxy include 2-hydroxyethyl, 2-hydroxypropyl, 1-hydroxy-1-methylethyl, methoxyethyl, ethoxyethyl or the like, preferably 2-hydroxyethyl or methoxyethyl. Examples of (C1-C4)alkoxy group optionally substituted with hydroxy or (C1-C4)alkoxy include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, 2-hydroxyethoxy, 2- or 3-hydroxypropoxy, methoxyethoxy, ethoxyethoxy, n-propoxyethoxy, isopropoxyethoxy, n-butoxyethoxy, methoxypropoxy, ethoxypropoxy, n-propoxypropoxy, isopropoxybutoxy, n-propoxybutoxy, 2-hydroxyethoxyethoxy or the like, preferably methoxy, ethoxy, methoxyethoxy or ethoxyethoxy. Methoxy or methoxyethoxy is particularly preferable. Examples of (C1-C4)alkylamino group optionally substituted with hydroxy or (C1-C4)alkoxy include 2-hydroxyethylamino, 2-hydroxyethylmethylamino, N,N-di(2-hydroxyethyl)amino, 2-hydroxypropylamino, 3-hydroxypropylamino, methoxyethylamino, ethoxyethylamino or the like, preferably 2-hydroxyethylamino, methoxyethylamino or 3-hydroxypropylamino. (C1-C4)alkanoylamino group optionally substituted with hydroxy or (C1-C4)alkoxy include acetylamino, n-propionylamino, isopropionylamino, hydroxyacetylamino, 2- or 3-hydroxy-n-propionylamino, 2- or 3-methoxy-n-propionylamino, butyrylamino or the like, among which acetylamino is particularly preferable. Ex
Miyazawa Takashi
Nagasaki Kazunobu
Ono Hiroaki
Shirasaki Yasuo
Tabei Toru
Kelly Cynthia H.
Nields & Lemack
Nippon Kayaku Kabushiki Kaisha
Xu Ling
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