Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-10-19
2004-05-04
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S592000, C534S651000, C534S793000, C534S797000, C534S817000, C549S394000, C106S031430, C106S031450, C106S031500
Reexamination Certificate
active
06730780
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an oil-soluble dye which can be suitably used for inks for inkjet recording, inks for ball-point pens, inks for markers, toners, paints such as lacquers, inks for felt pens, and the like. The oil-soluble dye as referred to in the present specification means a non-water-soluble dye in general.
The present invention also relates to a water-based ink, and more particularly to a water-based ink which can be suitably used for a water-based ink for inkjet recording and the like.
BACKGROUND ART
Oil-soluble dyes have been used for various applications mentioned above by dissolving the oil-soluble dye in an organic solvent and the like; dispersing the oil-soluble dye in water; or containing the oil-soluble dye in a polymer and thereafter dispersing the polymer in water.
Various oil-soluble dyes hitherto have been developed. However, there has not yet been developed an oil-soluble dye which has vivid color tone, which is excellent in light fastness and weathering resistance, which has acid resistance and alkali resistance, and which is capable of sufficiently dissolving in an organic solvent.
For instance, as oil-soluble magenta dyes, there have been known monoazoic dyes such as C.I. Solvent Red 1, 3; disazoic dyes such as C.I. Solvent Red 18, 24, 27; metal complex dyes such as C.I. Solvent Red 8, 132; anthraquinone dyes such as C.I. Solvent Red 52, 111, 145, 146, 149, 150, 151, 155; xantene dyes such as C.I. Solvent Red 49, 218; amino ketone dyes such as C.I. Solvent Red 109, 179, 180; perinone dyes such as C.I. Solvent Red 135, 176; and the like. Among them, monoazoic dyes, disazoic dyes, metal complex dyes, anthraquinone dyes, amino ketone dyes and oil-soluble perinone dyes have some defects such that they have low solubility in an organic solvent having a low polarity, such as toluene, and dull color tones. Also, the oil-soluble xantene dye has poor light fastness.
As yellow dyes, azoic dyes such as C.I. Solvent Yellow 14, 16, 29, 33, 44, 56, 77, 79, 82, 93, 114, 116, 117 have been marketed, but all of those have some defects such that they have low solubility in an organic solvent having a low polarity, and poor handling ability. As cyanine dyes, metal phthalocyanine dyes, triphenylmethane dyes and anthraquinone dyes such as C.I. Solvent Blue 14, 25, 35, 38, 70, 83, 94, 105 have been known, but those cyanine dyes have the same defects as those of the yellow dyes.
In addition, a disperse dye having water resistance, acid resistance and alkali resistance generally has low solubility in an organic solvent.
On the other hand, water-soluble dyes such as acid dyes include ones having vivid color tone and being excellent in fastness. When this dye is neutralized with, for instance, a basic compound having high hydrophobicity such as octylamine, the neutralized dye would possess solubility in an organic solvent with maintaining characteristics as a dye. However, the neutralized dye is poor in acid resistance and alkali resistance.
A carbon black-dispersed ink has been partly used as a black ink employed in a water-based ink for personal or office printers, and the like, excluding the industrial uses. Water-soluble dyes are used for most of the black inks. Also, the water-soluble dyes have been the mainstream of color inks.
However, the water-based ink in which a water-based dye has been used has a defect that its water resistance is drastically lowered.
In order to improve water resistance, inks made of a pigment dispersion have been developed. However, the inks, particularly color inks are insufficient for dispersibility, and color tone for high color reproduction quality, optical density and reliability.
An object of the present invention is to provide an oil-soluble dye which is excellent in water rest alkali resistance, acid resistance, light fastness and solvent solubility.
Another object of the present invention is to provide a water-based ink which has vivid color tone, which imparts excellent water resistance, light fastness and weathering resistance to printed characters, ad which is excellent in storage stability.
A further object of the present invention is to provide a water-based ink for inkjet recording, which would not cause clogging on the printer heads.
These objects and other objects of the present invention will be apparent from the following description.
DISCLOSURE OF INVENTION
According to the present invention, there are provided:
(1) an oil-soluble dye prepared by subjecting a water-soluble dye having at least one group selected from the group consisting of sulfonate group and carboxyl group in its molecule to amidation;
(2) a water-based ink comprising an oil-soluble dye prepared by subjecting a water-soluble dye having at least one group selected from the group consisting of sulfonate group and carboxyl group in its molecule to amidation; and
(3) a process for preparing an oil-soluble dye, comprising halogenating a water-soluble dye having at least one group selected from the group consisting of sulfonate group and carboxyl group in its molecule, and thereafter subjecting the resulting halogenated water-soluble dye to amidation.
BEST MODE FOR CARRYING OUT THE INVENTION
The water-soluble dye having at least one group selected from the group consisting of sulfonate group and carboxyl group in its molecule includes acid dyes, reactive dyes, direct dyes and food dyes, having at least one group selected from the group consisting of sulfonate group and carboxyl group in its molecule.
The acid dye includes, for instance,
C.I. Acid Yellow 1, 2, 5, 7, 16, 17, 23, 24, 26, 28, 29, 31, 41, 44, 48, 50, 51, 52, 52:1, 58, 60, 62, 63, 64, 67, 72, 76, 77, 94, 107, 108, 109, 110, 112, 115, 118, 119, 121, 122, 131, 132, 139, 140, 155, 156, 157, 158, 159, 172, 191, preferably C.I. Acid Yellow 5, 17, 23;
C.I. Acid Black 1, 3, 4, 7, 11, 12, 13, 14, 17, 18, 19, 23, 25, 29, 34, 36, 38, 39, 40, 41, 42, 44, 49, 50, 53, 55, 59, 61, 64, 70, 71, 72, 75, 76, 78, 79, 98, 99, 110, 111, 112, 114, 116, 118, 119, 122, 127, 128, 131, 135, 141, 142, 143, 151, 159, 161, 162, 163, 164, 165, 169, 172, 174, 190, 195, 196, 197, 199, 218, 219, 222, 227;
C.I. Acid Orange 7, 8, 10, 19, 20, 24, 28, 33, 41, 45, 51, 56, 64;
C.I. Acid Red 1, 4, 6, 8, 9, 13, 14, 15, 18, 19, 21, 26, 27, 30, 32, 34, 35, 37,40, 42, 44, 51, 52, 54, 57, 62, 75, 77, 80, 82, 83, 85, 87, 88, 89, 92, 94, 97, 106, 108, 110, 111, 114, 115, 117, 118, 119, 127, 128, 129, 130, 131, 133, 134, 135, 138, 143, 144, 145, 151, 152, 154, 155, 158, 168, 172, 176, 180, 183, 184, 186, 187, 194, 198, 199, 209, 211, 215, 216, 217, 219, 249, 252, 254, 256, 257, 261, 262, 263, 265, 266, 274, 276, 282, 283, 289, 299, 301, 305, 317, 318, 320, 321, 322, 336, 337, 361, 396, 397, preferably C.I. Acid Red 35, 37, 40, 52, 87, 92, 265, 289;
C.I. Acid Violet 5, 7, 11, 15, 34, 35, 41, 43, 47, 48, 49, 51, 75, 90, 103, 126;
C.I. Acid Blue 1, 7, 9, 15, 22, 23, 25, 27, 29, 40, 41, 43, 45, 51, 53, 54, 55, 56, 59, 60, 62, 72, 74, 76, 78, 80, 81, 82, 83, 90, 92, 93, 100, 102, 103, 104, 106, 111, 112, 113, 117, 120, 124, 126, 127, 129, 130, 131, 138, 140, 142, 143, 145, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 181, 182, 183, 184, 187, 192, 199, 203, 204, 205, 207, 220, 221, 229, 230, 232, 234, 236, 247, 249, 258, 260, 264, 271, 277, 278, 279, 280, 288, 290, 326, preferably C.I. Acid Blue 9;
C.I. Acid Green 3, 9, 12, 16, 19, 20, 25, 27, 41, 44;
C.I. Acid Brown 4, 14, and the like.
The reactive dye includes, for instance,
C.I. Reactive Black 1, 3, 4, 5, 6, 8, 12, 14, 21, 23, 26, 31, 32, 34, 37, preferably C.I. Reactive Black 37;
C.I. Reactive Yellow 1, 2, 3, 12, 13, 14, 15, 17, 18, 23, 24, 25, 26, 27, 29, 35, 37, 41, 42;
C.I. Reactive Orange 2, 5, 7, 16, 20, 24;
C.I. Reactive Red 3, 6, 7, 11, 12, 13, 15, 17, 19, 21, 22, 23, 24, 29, 35, 36, 37, 40, 41, 42, 43, 45, 49, 55, 63, 66, 84, 120, 180, 184, preferably C.I. Reactive Red 23, 24, 120, 180;
C.I. Reactive Violet 1, 2, 3, 4, 5, 6, 7, 8, 9, 16, 17, 22, 23, 24, 26, 27, 33, 34;
C.I. Reactive Blue 2, 3, 5, 7, 8, 10, 12, 13, 14, 15, 17, 18, 19, 20, 21, 25, 26, 27, 28, 29, 3
Kaida Kenji
Sakakibara Makoto
Tsutsumi Takehiro
Wakabayashi Shigemi
Birch & Stewart Kolasch & Birch, LLP
Kao Corporation
Powers Fiona T.
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