JPH09255882A - Xanthene-based pigment and ink jet recording liquid containing the same pigment - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new xanthene-based pigment excellent in light resistance of color image, excellent in color tone of good color reproducibility and especially excellent in light resistance and color tone of magenta color and useful for ink jet recording liquid. SOLUTION: This compound is represented by formula I [R1 and R2 are each H or a >=2C alkyl; Ph1 and Ph2 are each phenyl having at least one branched alkyl at ortho position; Y1 and Y2 are each sulfo or a halogen; Z is Y1 , carboxyl, sulfamoyl, etc.; An<-1> represents a pair ion, but when there a pair ion exists in the molecule, An<-1> is unnecessary; (l) and (m) are each 0-2; (n) is 1-5], e.g. sodium 3-isopropyl-4- [9-(2-carboxylphenyl)-6-(2- isopropylphenylamino)-3H-xanthene-3,3-diyl]amino}benzenesulfonate. The exemplified compound is obtained by reacting a compound of formula III with 0- isopropylaniline, sulfonating the resultant compound and treating the sulfonated compound with caustic soda.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a xanthene dye excellent in color tone and excellent in color image fastness and an ink jet recording liquid containing the dye.

[0002]

2. Description of the Related Art Pigments known as dyes and pigments are:
It is widely used in various applications such as dyeing materials for fibers, coloring materials for resins and paints, image forming materials for photography, printing, copying machines and printers, and light absorbing materials for color filters. The common problems of these dyes are optimization of absorption wavelength and waveform, improvement of molar absorption coefficient, improvement of storage stability such as light resistance and heat resistance.

In color image recording using yellow, magenta, cyan and black, for example, C.I. I. (Color Index), the conventionally known C.I. I. No. Dyes and pigments having the above have been widely studied. Particularly in the ink jet recording liquid for magenta, C.I. I. Xanthene-based, such as Acid Red 52,
C. I. It is known to use water-soluble azo dyes such as Direct Red 20, but the former has a problem in fastness such as light resistance, and the latter has spectral absorption related to color reproducibility such as lack of saturation. It had a characteristic problem.

To solve this problem, JP-A-59-1
33273, 59-147065, 59-15.
5089, 60-190478, 60-199.
Although phenylxanthene dyes substituted with an anilino group are described in JP-A No. 079, JP-A-5-295312 and the like, they have drawbacks that absorption at a short wavelength is not preferable as a hue and light resistance is insufficient. .

In order to form a full color or three primary colors, three kinds of dyes of yellow, magenta and cyan are required, and a magenta dye having particularly good absorption characteristics and storage stability is desired.

On the other hand, ink jet recording is a method of ejecting minute droplets of ink to record characters and images on a recording medium. This recording method enables recording on various recording media, easy colorization, and recent inkjet printer cost reduction, downsizing, high fineness, and high speed, The demand is expanding dramatically.

In this ink jet recording method,
Known are a continuous method in which ink is continuously ejected and the necessary droplets are attached to a recording medium by controlling the charge applied to the droplets, and an on-demand method in which only the necessary droplets are ejected. There is. Further, the on-demand method is a method in which a droplet is pressure-discharged by electro-mechanical conversion of a piezo element, a method in which a bubble is generated by electric-heat conversion to eject a pressure drop, and a method in which a droplet is sucked and discharged by an electrostatic force. Etc.

In the ink jet recording liquid for ink jet, for example, a color image which is suitable for the recording method selected from the above, has a high recorded image density and has a good color tone, and has light resistance, heat resistance and water resistance. Excellent fastness, fast fixing to the recording medium, no bleeding after recording, excellent ink storage stability,
It is required that there is no problem in safety such as toxicity and flammability and that it is inexpensive.

From these viewpoints, various inkjet recording liquids for inkjet have been proposed and studied, but the recording liquids satisfying many of the above requirements at the same time are extremely limited.

[0010]

DISCLOSURE OF THE INVENTION An object of the present invention is to provide a xanthene dye excellent in light fastness of a color image and an excellent color tone for good color reproducibility, and an ink jet recording liquid containing the dye, particularly magenta. It is an object of the present invention to provide a xanthene-based dye having excellent color lightfastness and color tone, and an inkjet recording liquid containing the dye.

[0011]

The above object of the present invention is attained by the following constitutions.

1. A xanthene-based dye represented by the following general formula I:

[0013]

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In the formula, R ₁ and R ₂ represent a hydrogen atom or an alkyl group having 2 or more carbon atoms, and when one is a hydrogen atom, the other is also a hydrogen atom, and when one is an alkyl group, the other is Is also an alkyl group. Ph ₁ and P
h ₂ represents a phenyl group having at least one branched alkyl group at the ortho position. Y ₁ and Y ₂ represent a sulfo group and a halogen atom, respectively. Z represents a sulfo group, a carboxyl group, a sulfamoyl group, a carbamoyl group or an alkoxycarbonyl group, and a halogen atom. l and m represent an integer of 0, 1 or 2, and n represents an integer of 1, 2, 3, 4 or 5. An-represents a counter anion. However, when a counter anion exists in the molecule, An ⁻ is not necessary. ] 2. The xanthene-based dye represented by the general formula I is represented by the following general formula II.

[0015]

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In the formula, R ₁ and R ₂ represent a hydrogen atom or an alkyl group having 2 or more carbon atoms. When one is a hydrogen atom, the other is also a hydrogen atom, and when one is an alkyl group, the other is Is also an alkyl group. X ₁ and X ₆ represent a branched alkyl group, and X ₂ , X ₃ , X ₄ , X ₅ , X ₇ ,
X ₈ , X ₉ and X ₁₀ represent a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, an acylamino group, an alkylsulfonyl group, a hydroxyalkyl group, an acyl group, an amino group, a cyano group, a hydroxy group, a sulfo group or a carboxyl group. Represent. Z ₁ ⁻ represents an anion of a sulfo group or a carboxyl group.

3. An ink jet recording liquid comprising a xanthene dye represented by the general formula I or II.

The present invention will be described in more detail below.

First, the xanthene dye represented by the general formula I will be described.

In the general formula I, R ₁ and R ₂ represent a hydrogen atom or an alkyl group having 2 or more carbon atoms (eg, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group). When one is a hydrogen atom, the other is also a hydrogen atom, and when one is an alkyl group, the other is an alkyl group. Ph ₁ and Ph ₂ each represent a phenyl group having at least one branched alkyl group (eg, isopropyl group, isobutyl group, tert-butyl group, tert-pentyl group, tert-aryoctyl group) at the ortho position.

Other substituents which can be introduced at other positions of Ph ₁ and Ph ₂ may be introduced (for example, a halogen atom, an alkyl group, an acyl group, an acylamino group, an alkoxy group, an alkoxycarbonyl group, an alkylsulfonyl). Base,
Cyano group, nitro group, hydroxy group, carboxyl group,
Sulfo group).

Y ₁ and Y ₂ represent a sulfo group and a halogen atom, respectively. Z represents a sulfo group, a carboxyl group, a sulfamoyl group, a carbamoyl group or an alkoxycarbonyl group, and a halogen atom. l and m are 0, 1, or 2
Represents an integer of 1, and n represents an integer of 1, 2, 3, 4 or 5.

[0023] An ^- represents a counter anion. As the counter anion, a halide ion (for example, chloride ion,
Bromide ion, etc.), sulfate ion, organic sulfonate ion (eg, alkyl sulfonate having 1 to 20 carbon atoms, benzene sulfonate, etc.), fatty acid ion (aliphatic carboxylate having 1 to 20 carbon atoms, etc.), benzoate ion, oxalic acid Examples thereof include an ion, a perchlorate ion, a tetrafluoroborate ion or a hexafluorophosphate ion. However, when the molecule has a counter anion as a substituent (for example, when Z is a sulfo group or a carboxyl group), An ⁻ is not required.

In the general formula I, the structure having preferable color tone and weather resistance is a case where l and m are 0, and more preferably 1
And m is 0, Z is a sulfo group or a carboxyl group, and An ⁻ is unnecessary.

In the xanthene dye represented by the general formula I,
The formula II has been narrowed down to a more preferable structure in terms of performance.
It is a xanthene dye represented by.

In the general formula II, R ₁ and R ₂ represent a hydrogen atom or an alkyl group having 2 or more carbon atoms (eg ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group). When one is a hydrogen atom, the other is also a hydrogen atom, and when one is an alkyl group, the other is an alkyl group.

Of R ₁ and R ₂ , a hydrogen atom is preferable. X ₁ and X ₆ represent a branched alkyl group (eg, isopropyl group, isobutyl group, tert-butyl group, tert-pentyl group, tert-aryoctyl group, etc.),
_{X 2, X 3, X 4} , X 5, X 7, X 8, X 9, X 10 is a hydrogen atom, an alkyl group (e.g., methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, Pentyl group etc.), aralkyl group (eg benzyl group, phenethyl group etc.), alkenyl group (eg allyl group, 2-
Butenyl group, etc.), acylamino group (eg, acetylamino group, propionylamino group, butyrylamino group, pivalylamino group, octanoylamino group, benzoylamino group, etc.), alkylsulfonyl group (eg, methylsulfonyl group, ethylsulfonyl group, butyl) Sulfonyl group, octylsulfonyl group), hydroxyalkyl group (for example, hydroxymethyl group, hydroxyethyl group, etc.), acyl group (acetyl group, propionyl group, butyryl group, isobutyryl group, pivalyl group, octanoyl group, etc.), amino group, It represents a cyano group, a hydroxy group, a sulfo group or a carboxyl group.

X ₂ , X ₃ , X ₄ , X ₅ , X ₇ , X ₈ , X ₉ , X
Among ₁₀ , preferably a hydrogen atom, an alkyl group, a sulfo group,
Carboxyl group, more preferably X ₃ , X ₄ , X
_This is the case where one or two sulfo groups or carboxyl groups are present at the ₈ and X ₉ positions and the other is a hydrogen atom. Z
₁ ^- represents a sulfo group, an anionic carboxyl group. Z
₁ ^- of preferably the anion of a carboxyl group.

The light resistance of the xanthene-based dye of the present invention is dramatically improved by substituting it with an anilino group having a branched alkyl group at the ortho position as a substituent of the xanthene-based dye. Although the mechanism of improving the light resistance of the xanthene dye of the present invention is not necessarily clear, it is considered to prevent molecular aggregation due to the steric bulkiness of the branched alkyl group and prevent active oxygen from approaching the site having a high electron density.

Specific examples of the compounds of the dyes represented by the general formula I and the general formula II are shown below, but the invention is not limited thereto.

[0031]

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[0032]

[Chemical 6]

[0033]

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[0034]

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[0035]

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The above compound can be easily synthesized by a conventionally known method for synthesizing a xanthene dye.

The synthesis of the above compound will be described below.

Synthesis Example 1 Synthesis Reaction Scheme 1 of Compound Example 1

[0039]

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20 g of raw material 1, 31 g of raw material 2 and 9 g of zinc chloride were sequentially charged into a flask, and the temperature was from 140 ° C to 160 ° C.
For 2 hours. The reaction solution was poured into 100 ml of diluted hydrochloric acid, and the precipitated crystals were collected by filtration. After washing with water and drying, 23 g of raw material 3 was obtained. The structure was confirmed by NMR and mass spectrometry. 20m of fuming sulfuric acid was placed in the flask and the obtained 20
g of raw material 3 was gradually added at an internal temperature of 30 ° C. or lower. 100m
It was poured into 1 liter of cold saturated saline and the precipitated crystal was collected by filtration. Further, it was dissolved in 50 ml of water, made weak alkaline with caustic soda, and then crystallized by salting out, collected by filtration and dried to obtain 15 g of Exemplified Compound 1. The structure was confirmed by NMR and mass spectrometry.

Synthesis Example 2 Synthesis Reaction Scheme 1 of Compound Example 5

[0042]

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21 g of the raw material 4, 15 g of the raw material 2 and 5 g of magnesium oxide were dissolved in 50 ml of ethylene glycol and reacted at 140 ° C. to 160 ° C. for 2 hours. The reaction solution was poured into 100 ml of diluted hydrochloric acid, and the precipitated crystals were collected by filtration. It was washed with water and dried to obtain 18 g of raw material 6. The structure was confirmed by NMR and mass spectrometry. 20 m of fuming sulfuric acid was placed in a flask, and 15 g of the obtained raw material 6 was gradually added at an internal temperature of 30 ° C or lower. It was poured into 100 ml of cold saturated saline and the precipitated crystals were collected by filtration. Further, after dissolving in 30 ml of a caustic soda aqueous solution, salt precipitation was performed to precipitate crystals, which were collected by filtration and dried to obtain 10 g of Exemplified Compound 5. The structure was confirmed by NMR and mass spectrometry.

The ink jet recording liquid containing the xanthene dye represented by the general formula I or the general formula II (hereinafter, also referred to as the dye of the present invention) may be an aqueous ink, an oil ink, a solid (phase change) ink, or the like. Although various solvent systems can be used, aqueous ink is particularly preferably used as the solvent system.

The water-based ink solvent is, in addition to the dye of the present invention,
Water and water-soluble organic solvents are generally used as solvents. Examples of water-soluble organic solvents include alcohols (eg, methanol, ethanol, propanol, i-propanol,
Butanol, i-butanol, sec-butanol, t
-Butanol, pentanol, hexanol, cyclohexanol, benzyl alcohol, etc.), polyhydric alcohols (for example, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol,
Polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol, etc.), polyhydric alcohol ethers (eg ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, ethylene glycol monophenyl ether, propylene glycol Cole monophenyl ether, etc., amines (eg ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenediamine, triethylenetetramine, tetraethylenepentamine) , Polyethyleneimine, pentamethyldiethylenetriamine, tetramethylpropylenediamine, etc.), amides (eg, formamide, N, N-dimethylformamide, N, N-dimethylacetamide, etc.),
Heterocycles (for example, 2-pyrrolidone, N-methyl-2-pyrrolidone, cyclohexylpyrrolidone, 2-oxazolidone, 1,3-dimethyl-2-imidazolidinone, etc.),
Sulfoxides (eg dimethyl sulfoxide), sulfones (eg sulfolane), urea, acetonitrile,
Acetone and the like can be mentioned.

In the aqueous ink solvent as described above, the dye of the present invention can be used as it is if it is soluble in the solvent system. On the other hand, when it is a solid that is insoluble as it is, the dye is dispersed in various dispersing machines (for example, ball mill, sand mill, attritor, roll mill, agitator mill, Henschel mixer, colloid mill, ultrasonic homogenizer, pearl mill, jet mill, ong mill, etc.). It can be used as fine particles, or the dye can be dissolved in a soluble organic solvent and then dispersed in the solvent system together with a polymer dispersant and a surfactant. Furthermore,
When it is a liquid or a semi-molten substance which is insoluble as it is, it can be dispersed in the solvent system as it is or by dissolving it in a soluble organic solvent together with a polymer dispersant and a surfactant.

A specific method for preparing such an aqueous ink solvent is described in, for example, JP-A-5-148436 and JP-A-5-148436.
295312, 7-97541, 7-8251.
No. 5, No. 7-118584, etc. can be referred to.

The oil-based ink solvent uses an organic solvent as a solvent in addition to the dye of the present invention. Examples of the solvent for the oil-based ink include alcohols (for example, pentanol, heptanol, octanol, phenylethyl alcohol, phenylpropyl alcohol, furfuryl alcohol, and anyl) in addition to those exemplified as the water-soluble organic solvent in the above water-based ink solvent. Alcohol etc.), esters (ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, propylene glycol diacetate, ethyl acetate, amyl acetate, benzyl acetate, phenylethyl acetate, phenoxyethyl acetate, phenylethyl acetate, propione Acid benzyl, ethyl benzoate, butyl benzoate, butyl laurate, myristic acid-i-
Propyl, triethyl phosphate, tributyl phosphate, diethyl phthalate, dibutyl phthalate, diethyl malonate, dipropyl malonate, diethyl diethyl malonate, diethyl succinate, dibutyl succinate, diethyl glutarate, diethyl adipate, dipropyl adipate, adipine Dibutyl acid, di (2-methoxyethyl adipate), diethyl sebacate, diethyl maleate, dibutyl maleate, dioctyl maleate, diethyl fumarate, dioctyl fumarate, -3-hexenyl cinnamate, ethers (for example, Butyl phenyl ether, benzyl ethyl ether, hexyl ether, etc.), ketones (eg, benzyl methyl ketone, benzyl acetone, diacetone alcohol, cyclohexanone, etc.), hydrocarbons (eg, petroleum ether, petroleum ether) Jill, tetralin, decalin, t
-Amylbenzene, dimethylnaphthalene, etc.), amides (eg, N, N-diethyldodecane amide) and the like.

In the oil-based ink solvent as described above, the dye of the present invention can be dissolved and used as it is,
Further, a resinous dispersant or a binder may be used in combination for dispersion or dissolution. For specific methods for preparing such oil-based ink solvents, the methods described in JP-A-3-231975, JP-A-5-508883 and the like can be referred to.

As the solid (phase change) ink solvent, in addition to the ink jet recording liquid of the present invention, a solvent which is solid at room temperature and which is a liquid state melted at the time of jetting the ink jet recording liquid is used. Examples of such phase change solvents include natural waxes (eg, beeswax, carnauba wax, rice wax, wood wax, jojoba oil, spermaceti wax, candelilla wax, lanolin, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax). , Petrolactam, etc.), polyethylene wax derivatives, chlorinated hydrocarbons, organic acids (eg palmitic acid, stearic acid, behenic acid, tiglic acid, 2
-Acetonaphthone behenic acid, 12-hydroxystearic acid, dihydroxystearic acid, etc., organic acid esters (for example, esters of the above organic acids with alcohols such as glycerin, diethylene glycol, ethylene glycol, etc.), alcohols (for example, dodecanol, tetradeca) Nole, hexadecanol, eicosanol, docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicosenol, docosenol, pinene glycol, hinokiol, butynediol, nonanediol, isophthalyl alcohol, Mesicillin, terephthalyl alcohol, hexanediol, decanediol, dodecanediol, tetradecanediol, hexadecanediene Alcohol, docosane diol, tetracosan diol, terpineol, phenylglycerin, eicosane diol, octane diol, phenyl propylene glycol, bisphenol A, para-alpha cumyl phenol, etc., ketones (for example, benzoylacetone, diacetobenzene, benzophenone, Tricosanone, heptacosanone, heptatriacontanone, hentriacontanone, stearone, laurone, dianisole, etc., amides (eg oleic acid amide, lauric acid amide, stearic acid amide, ricinoleic acid amide, palmitic acid amide, tetrahydrofuranic acid amide, eruca) Acid amide, myristic acid amide, 12-hydroxystearic acid amide, N-stearyl erucic acid amide, N
Oleyl stearamide, N, N'-ethylenebislauric acid amide, N, N'-ethylenebisstearic acid amide, N, N'-ethylenebisoleic acid amide, N, N'-methylenebisstearic acid amide; N,
N'-ethylenebisbehenamide, N, N'-xylylenebisstearic acid amide, N, N'-butylenebisstearic acid amide, N, N'-dioleyladipamide, N, N'-distearyl Adipic amide,
N, N'-dioleyl sebacic acid amide, N, N'-distearyl sebacic acid amide, N, N'-distearyl isophthalic acid amide, phenacetin, toluamide, acetamide, oleic acid dimer / ethylenediamine / stearic acid ( (A molar ratio of 1: 2: 2) such as a reaction product of a dimer acid, a diamine and a fatty acid such as tetraamide), a sulfonamide (for example, paratoluenesulfonamide, ethylbenzenesulfonamide, butylbenzenesulfonamide, etc.), a silicone (For example, silicone SH6018
(Toray Silicone), Silicone KR215,216,
220 (Shin-Etsu Silicone) and the like, and coumarones (for example,
Escuron G-90 (Nippon Steel Chemicals, etc.), cholesterol fatty acid ester (eg, cholesterol stearate, cholesterol palmitate, cholesterol myristate, cholesterol behenate, cholesterol laurate, cholesterol melicinate), saccharide fatty acid ester (stearic acid) Saccharose, saccharose palmitate, saccharose behenate, saccharose laurate, saccharose melicinate, lactose stearate, lactose palmitate, lactose myristate, lactose behenate, lactose laurate, lactose melicate and the like).

The phase change temperature in the solid-liquid phase change of the solid ink solvent is preferably 60 ° C. or higher, and 80
It is more preferable that the temperature is 150 ° C.

In the solid ink solvent as described above, the dye of the present invention can be used as it is by dissolving it in a solvent in a heated and molten state, or can be used by dispersing or dissolving it together with a resinous dispersant or a binder. Can also be used.

The specific method for preparing such solid ink solvent is described in JP-A-5-186723 and JP-A-7-704.
The method described in No. 90, etc. can be referred to.

The above-mentioned water-based, oil-based, and solid ink solvents preferably have a flying viscosity of 40 cps or less, more preferably 30 cps or less.

The surface tension of the ink jet recording liquid of the present invention during flight is preferably 20 dyn / cm or more, more preferably 30 to 80 dyn / cm.

In the ink jet recording liquid of the present invention,
The dyes represented by the general formula I and the general formula II of the present invention are preferably used in the range of 0.1 to 25% by weight, and in the range of 0.5 to 10% by weight, based on the total amount of the inkjet recording liquid. More preferably.

In the ink jet recording liquid of the present invention, a viscosity adjusting agent and a surface tension adjusting agent are used according to the purpose of improving ejection stability, compatibility with print heads and ink cartridges, storage stability, image storability, and other various performances. An agent, a specific resistance adjusting agent, a film-forming agent, a dispersant, a surfactant, an ultraviolet absorber, an antioxidant, an anti-fading agent, a mildew proofing agent, and a rust preventive agent can also be added.

The ink jet recording liquid of the present invention is not particularly limited as to the recording method used, but it can be preferably used as an ink for an on-demand ink jet printer. Examples of the on-demand type method include an electro-mechanical conversion method (for example, a single cavity type, a double cavity type, a bender type, a piston type, a shear mode type, a shared wall type, etc.), and an electric-heat conversion method (for example, a thermal inkjet type). , Bubble jet type, etc., electrostatic attraction type (eg electric field control type, slit jet type etc.), discharge type (eg spark jet type) etc. can be mentioned as specific examples.

[0059]

EXAMPLES The present invention will be described more specifically with reference to examples, but the present invention is not limited to the embodiments in the examples.

Example 1 Each ink composition having the composition shown in Table 1 was used to record on an inkjet-dedicated coated paper with an inkjet printer MJ-5000C (manufactured by Seiko Epson Corporation, electro-mechanical conversion system). A magenta image sample was prepared. Table 1 shows the results of evaluation of light resistance and color tone defined as follows using this sample.

Light resistance: PDA-65 (manufactured by Konica Corporation)
The residual ratio of the image of the sample after the bombardment with a xenon fade meter for 24 hours to the unbombarded sample calculated from the measurement of the reflection density with green light.

Light resistance (%) = (green light reflection density of exposed sample / green light reflection density of unexposed sample) × 100 Color tone: blue using PDA-65 (manufactured by Konica Corporation),
The reflection densities of green and red light were measured, and the relative blue light reflection density and the relative red light reflection density when the reflection density of green light was normalized to 1 were evaluated according to the following criteria.

That is, ◯ represents a magenta image having a good color tone with little improper absorption in the wavelength regions of blue light and red light.

◯: When relative blue light reflection density is less than 0.25 and relative red light reflection density is less than 0.10 Δb: When relative blue light reflection density is 0.25 or more and relative red light reflection density is less than 0.10. Δr: When relative blue light reflection density is less than 0.25 and relative red light reflection density is 0.10 or more ×: When relative blue light reflection density is 0.25 or more and relative red light reflection density is 0.10 or more The unit of the amount of each compound of 1 is weight% with respect to the total inkjet recording liquid. Comparison-1 and Comparison- described in the table
The structures of 2, Comparative-3 and Surfactant-1 are shown below.

[0065]

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[0066]

[Table 1]

As is clear from the results shown in Table 1, the dye of the present invention and the ink jet recording liquid containing the dye have higher light resistance than those of the comparative dye and the ink jet recording liquid containing the dye. It can be seen that the color tone is excellent, and there is little improper absorption in the blue and red light regions with respect to the reflection density in the green light region, and the color tone is good.

Further, it can be used without any problems in the continuous discharge test of the printer, and the high reliability of the electro-mechanical conversion system of the ink jet recording liquid of the present invention was confirmed.

Example 2 Using each ink composition having the composition shown in Table 2, a sample recorded on a glossy paper for exclusive use for inkjet by an inkjet printer BJC-600J (manufactured by Canon Inc., electric-thermal conversion system) was used. Obtained. Using this sample, light resistance and color tone were evaluated in the same manner as in Example 1 and the results are shown in Table 2. The unit of the amount of each compound in Table 2 is% by weight with respect to the total ink jet recording liquid, and the definition of the compounds of Comparative-1, Comparative-2, and Comparative-3 and the evaluation items are the same as in Example 1.

[0070]

[Table 2]

As is clear from the results shown in Table 2, the dye of the present invention and the ink jet recording liquid containing the dye have higher light resistance than those of the comparative dye and the ink jet recording liquid containing the dye. It can be seen that the color tone is excellent, and there is little improper absorption in the blue and red light regions with respect to the reflection density in the green light region, and the color tone is good.

In the printer system of the present invention, it was confirmed that the ink jet recording liquid of the present invention had compatibility with the electro-thermal conversion system without any abnormality of the head due to thermal deterioration.

[0073]

As demonstrated in the examples, the xanthene dye according to the present invention and the ink jet recording liquid containing the dye have excellent light resistance of color images and excellent color tone for good color reproducibility. In particular, it has an excellent effect on light resistance and color tone of magenta color.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hitoshi Morimoto, Konica Stock Company, Hino City, Tokyo 1 Konica Stock Company (72) Inventor, Daisuke Ishibashi 1, Sakura City, Hino City, Tokyo Konica Stock Company, in-house

Claims (3)

[Claims] 1. A xanthene dye represented by the following general formula I: Embedded image [In the formula, R ₁ and R ₂ represent a hydrogen atom or an alkyl group having 2 or more carbon atoms. When one is a hydrogen atom, the other is a hydrogen atom, and when one is an alkyl group, the other is an alkyl group. Shall be the basis. Ph ₁ and Ph ₂ represent a phenyl group having at least one branched alkyl group at the ortho position. Y ₁ and Y ₂ represent a sulfo group and a halogen atom, respectively. Z represents a sulfo group, a carboxyl group, a sulfamoyl group, a carbamoyl group or an alkoxycarbonyl group, and a halogen atom. l and m represent an integer of 0, 1 or 2, and n represents an integer of 1, 2, 3, 4 or 5. An ⁻ represents a counter anion. However, when a counter anion exists in the molecule, An ⁻ is not necessary. ] 2. The xanthene-based dye represented by the general formula I is represented by the following general formula II.
The xanthene-based dye described in 1. Embedded image [In the formula, R ₁ and R ₂ represent a hydrogen atom or an alkyl group having 2 or more carbon atoms. When one is a hydrogen atom, the other is a hydrogen atom, and when one is an alkyl group, the other is an alkyl group. Shall be the basis. X ₁ and X ₆ represent a branched alkyl group, and are X ₂ , X ₃ , X ₄ , X ₅ , X ₇ , X ₈ , X ₉ ,
X ₁₀ represents a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group, an acylamino group, an alkylsulfonyl group, a hydroxyalkyl group, an acyl group, an amino group, a cyano group, a hydroxy group, a sulfo group or a carboxyl group. Z
₁ ^- represents a sulfo group, an anionic carboxyl group. ] 3. An ink jet recording liquid containing a xanthene dye represented by the general formula I or II.