JP5048479B2 - Disperse dye, disperse dye composition, ink for ink-jet printing, dyeing method and dyed material using these - Google Patents

Description

  The present invention is a novel orange disperse dye which is particularly useful as a sheet for automobile interiors, which is excellent in dyeability of hydrophobic fiber materials, has high light fastness and excellent sublimation fastness, and also has good build-up property. The present invention relates to a disperse dye composition, an ink for inkjet printing, a dyeing method using the ink, and a dyed product.

  In recent years, hydrophobic fiber materials have been used as materials for automobile interiors, particularly seat seats, and in particular, polyester fibers are often used. In recent years, richer colors have come to be demanded by improving fashionability. However, in the case of a car interior sheet, yellow is discolored by exposure at high temperature for a long time, which causes discoloration of a mixed dyed product of red and blue.

  There is a test method according to JIS L 0842 as a normal light resistance evaluation method, but a more severe test method, a xenon arc lamp, is used as a light resistance evaluation method for dyes used in automobile interior seats. There is an accelerated test method (for example, Toyota method). When this test method is used, a dye having poor light resistance is significantly different from a normal test method in comparison with a good dye.

  As countermeasures against the phenomenon in which yellow is discolored by high-temperature and long-time exposure, for example, Patent Document 1, Patent Document 2, Patent Document 3, and the like have proposed highly light-resistant yellow disperse dye compositions.

  However, when the yellow disperse dye composition described in Patent Documents 1 to 3 is used as a blending component with red and blue to obtain a brown, amber or black dyed product, it has high light fastness. However, there is a problem that it is inferior in build-up property.

For this reason, an orange dye is used as a blending component of the brown, amber or black disperse dye. As conventional orange dyes, for example, dyes of the following formula (1) and dyes of the following formula (2) are generally widely used.

  However, the above-mentioned orange dyes are not sufficiently light-resistant to be used as dyes for automobile interior sheets and cannot be used for toning with highly light-resistant disperse dyes.

In addition, as an orange dye having good light resistance, a dye represented by the following formula (3) described in Example 1 of Patent Document 4 and a dye represented by the following formula (4) are proposed in Patent Document 5. .

However, the dye of the formula (3) is very excellent in light resistance, but is not good in sublimation fastness and has difficulty in build-up property. Further, the dye of the formula (4) has very good build-up property, but does not have good sublimation fastness, and does not have sufficient light resistance to be used as a dye for a vehicle interior sheet.
JP-A-6-345899 JP-A-6-166828 JP 2001-342375 A JP 63-135455 A JP 2001-98177 A, [Claim 2], Formula (108)

  In order to solve the above-mentioned conventional problems, the present invention is excellent in dyeing properties of hydrophobic fiber materials, has high light fastness and excellent sublimation fastness, and has a good build-up property. Disclosed are a novel orange disperse dye useful as a dye to be used, a yellow to orange, brown, amber, black disperse dye composition using the same, an ink for inkjet printing, a dyeing method using the same, and a dyed product. This is the issue.

The orange disperse dye of the present invention has the following formula [1]

[In the formula [1], X ₁ represents a chlorine atom or a bromine atom, and R ₁ is substituted with one or more of a benzoyl group, a cyanoethyl group, a C ₁ -C ₄ alkyl group, a phenyl group, or a C ₁ -C ₄ alkyl. Represents a phenyl group. ]
And is characterized by being an orange disperse dye.

The yellow to orange disperse dye composition of the present invention (hereinafter referred to as “first disperse dye composition”) is represented by the orange disperse dye represented by the above formula [1] and the following formula [2]. A dye represented by the following formula [3], a dye represented by the following formula [4], a dye represented by the following formula [5], and a dye represented by the following formula [6] And at least one selected from yellowish dyes.

[In the above formula [4], _{X 2} represents a hydrogen atom or a bromine atom, _{R 2} represents a hydrogen atom or -COOC ₂ H ₄ OC ₂ H ₅ group. ]

[In the above formula [6], R ₃ represents a C ₁ -C ₄ alkyl group, a phenyl group, or a phenyl group substituted with one or more C ₁ -C ₄ alkyl. ]

The disperse dye composition of the present invention (hereinafter referred to as “second disperse dye composition”) includes an orange disperse dye represented by the formula [1] and a dye represented by the following formula [17]. It is characterized by including.

Further, the disperse dye composition of the present invention (hereinafter referred to as “third disperse dye composition”) is an orange disperse dye represented by the formula [1] or 1 of the yellow to orange disperse dye composition. First disperse orange-based disperse dye composition which is a seed, a dye represented by the following formula [7], a dye represented by the following formula [8], a dye represented by the following formula [9], the following At least one red dye selected from the dye represented by the formula [10] and the dye represented by the following formula [11], a dye represented by the following formula [12], and the following formula [13] A dye, a dye represented by the following formula [14], a dye represented by the following formula [15], and at least one blue dye selected from the dye represented by the following formula [16]. Features.

[In the formula [8], _{R 4} represents a hydrogen atom, -OCH ₃ group, _-OC 2 _{H 5} group, or _{-SO 2 NHC 3 H 6 OC 2} H 5. ]

[In the above formula [10], R ₅ represents a phenyl group, a phenyl group substituted with one or more C _{1 to} C ₄ alkyl, a —COOC ₂ H ₅ group or a —COOC ₆ H ₅ group. ]

[In the above formula [11], _{R 6} represents a hydrogen atom, -CH ₃ group or _-C 2 _{H 5} group. ]

[Representing the formula [13] in, _{R 7} is _{-C 3 H} 6 OCH 3 group or _{-C 3 H 6 OC 2 H 4} OCH 3 group. ]

[In the formula [15], _{R 8} represents a hydroxyl group, -OCH ₃ group or _-OC 2 _{H 5} group. ]

[In the formula [16], _{X 3} represents a hydrogen atom or a bromine atom. ]

  The first orange disperse dye composition for blending in the yellow to orange first disperse dye composition is 65 to 98% by weight of the orange disperse dye and 2 to 35 of the yellow dye. It means that it contains orange and is orange and is for compounding.

  Also, the disperse dye composition of the present invention (hereinafter referred to as “fourth disperse dye composition”) is a second disperse orange disperse dye composition which is one of the second disperse dye compositions. And a dye represented by the following formula [7], a dye represented by the following formula [8], a dye represented by the following formula [9], a dye represented by the following formula [10], and the following formula [ 11], a dye represented by the following formula [12], a dye represented by the following formula [13], a dye represented by the following formula [14], It includes at least one blue dye selected from a dye represented by the formula [15] and a dye represented by the following formula [16]. The second disperse orange-based disperse dye composition in the second disperse dye composition is 20 to 80% by weight of the orange disperse dye and 20 to 20% of the dye represented by the formula [17]. It means 80% by weight, orange color and for compounding.

  The method for dyeing a hydrophobic fiber material of the present invention is characterized by using the orange disperse dye, the first to fourth disperse dye compositions, or the first or second blending orange disperse dye composition. To do.

  The ink for inkjet textile printing of the present invention is characterized by containing the orange disperse dye, the first to fourth disperse dye compositions, or the first or second orange disperse dye composition.

  The orange disperse dye, the disperse dye composition, and the ink for inkjet printing of the present invention are excellent in dyeing properties such as build-up property, dyeing of hydrophobic fiber materials, excellent in sublimation fastness, particularly high light fastness. It is also suitable for dyeing required automotive interior sheets. Moreover, the dyeing | staining method and dyeing | staining thing using these can also be provided.

As described above, the orange disperse dye of the present invention is an orange disperse dye represented by the formula [1].

[In the formula [1], X ₁ represents a chlorine atom or a bromine atom, and R ₁ is substituted with one or more of a benzoyl group, a cyanoethyl group, a C ₁ -C ₄ alkyl group, a phenyl group, or a C ₁ -C ₄ alkyl. Represents a phenyl group. ]

In the present specification, the C ₁ -C ₄ alkyl group means a linear or branched alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec- Examples include butyl and tert-butyl. Wherein _C 1 -C ₄ alkyl group is preferably n- butyl.

As the phenyl group substituted by one or more in the _C 1 -C ₄ alkyl, such as, _C 1 -C ₄ alkyl groups of 1 to 5 phenyl groups are those substituted. If two or more C ₁ -C ₄ alkyl group on the phenyl group is substituted, the alkyl group may be the same or different. Examples of the substituted phenyl group include 4-methylphenyl, 2,4-dimethylphenyl, 4-ethyl, 2,4,6-trimethylphenyl, and the like.

As the orange disperse dye represented by the formula [1], in the formula [1],
X ₁ represents a chlorine atom, R ₁ represents a benzoyl group,
X ₁ represents a chlorine atom, R ₁ represents a cyanoethyl group,
X ₁ represents a chlorine atom, R ₁ represents a C ₁ -C ₄ alkyl group,
X ₁ represents a chlorine atom, R ₁ represents a phenyl group,
X ₁ represents a chlorine atom, and R ₁ represents a phenyl group substituted with a C ₁ -C ₄ alkyl group,
X ₁ represents a bromine atom, R ₁ represents a benzoyl group,
X ₁ represents a bromine atom and R ₁ represents a cyanoethyl group,
X ₁ represents a bromine atom, R ₁ represents a C ₁ -C ₄ alkyl group,
X ₁ represents a bromine atom and R ₁ represents a phenyl group, and X ₁ represents a bromine atom, and an represents a phenyl group R ₁ is substituted by C ₁ -C ₄ alkyl group.

As the orange disperse dye represented by the formula [1], in the formula [1], X ₁ represents a chlorine atom, R ₁ represents a benzoyl group, and X ₁ represents a chlorine atom. It is preferable that ₁ represents a cyanoethyl group, and in the formula [1], it is more preferable that X ₁ represents a chlorine atom and R ₁ represents a benzoyl group.

In the present invention, as a preferred specific example of the formula [1], in the formula [1], X ₁ represents a chlorine atom and R ₁ represents a benzoyl group. In the formula [1], X ₁ represents a bromine atom and R ₁ represents a cyanoethyl group. In the formula [1], the dye represented by the following formula [1-2] Examples of the compound in which X ₁ represents a bromine atom and R ₁ represents a C ₄ alkyl group include dyes represented by the following formula [1-3].

  Among the above dyes, the dye [1-1] is particularly preferable from the viewpoint of light resistance.

A method for producing the orange disperse dye represented by the formula [1] will be described below. First, the compound of the following formula [100] is diazotized using a nitrosating agent or nitrosylsulfuric acid in a mineral acid or an organic carboxylic acid in the presence of optionally added water to obtain a diazo compound. Examples of the organic carboxylic acid used include acetic acid and propionic acid. Examples of the mineral acid include hydrochloric acid, phosphoric acid and sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite such as sodium nitrite in a solid or aqueous solution. The diazotization temperature is preferably −5 to 30 ° C., more preferably 0 to 20 ° C.

[In the formula [100], X ₁ represents a chlorine atom or a bromine atom. ]

A solution of the obtained diazo compound is added to a solution or suspension of the compound represented by the following formula [101] as a coupler in a temperature range of, for example, 0 to 35 ° C., and represented by the formula [1]. To obtain the compound. The pH of the coupler solution or suspension initially introduced is preferably weakly acidic. Alternatively, a compound represented by the following formula [101] as a coupler may be added to a solution of a weak acid such as acetic acid to form a dissolved state or a suspension state, and a diazo compound solution may be added thereto. In this case, it may be advantageous to add a buffering agent such as sodium acetate.

[In the formula [101], R ₁ represents a benzoyl group, a cyanoethyl group, a C ₁ -C ₄ alkyl group, a phenyl group, or a phenyl group substituted with one or more C ₁ -C ₄ alkyl. ]

  In addition, the compound represented by the following formula [100], which is a raw material of the diazo compound of the formula [1], is known as a diazo component of the dye (IV) in US Pat. No. 3,342,804.

In addition, among the compounds represented by the formula [101], when R ₁ is a benzoyl group, for example, C.I. I. It is widely known and used as a coupler for Disperse Orange 73.

A compound represented by the formula [101] wherein R ₁ is a cyanoethyl group or a butyl group is also a known compound that is widely known and used, and can be synthesized by a known method.

  As a result of intensive studies, the present inventors have surprisingly found that the dye represented by the formula [1] is excellent in dyeability of the hydrophobic fiber material, has high light fastness, and sublimation fastness. The present invention has been completed by discovering that it is an orange disperse dye that has excellent build-up properties and is particularly useful as a dye for automobile interior sheets.

  The orange disperse dye represented by the formula [1] has good light fastness even in the test method based on the Toyota method when used alone, and in all of sublimation fastness and build-up property. Are better.

  Therefore, by blending with other high light-resistant disperse dyes, disperse dye compositions for yellow to orange, brown, amber, and black can be provided.

  A yellow to orange first disperse dye composition obtained by blending the orange disperse dye of the present invention with a yellow dye will be described below.

  Since the orange disperse dye of the present invention is slightly reddish, it can be reddish yellow even if mixed in a small amount with a yellow dye. In addition, by changing the blending ratio, various hues from yellow to orange can be obtained.

  In order to maintain light resistance, the yellow dye used in the blending must also have the same fastness. Therefore, the dye represented by the formula [2] and the dye represented by the formula [3] The dye represented by Formula [4], the dye represented by Formula [5], and the yellow dye represented by Formula [6] are used.

  Among the yellow to orange first disperse dye compositions of the present invention, the yellow disperse dye composition comprises 3 to 20% by weight of the orange disperse dye represented by the formula [1] and the formula [2]. A dye represented by the formula [3], a dye represented by the formula [4], a dye represented by the formula [5], and a dye represented by the formula [6]. It is preferable to contain 80 to 97% by weight of at least one selected from yellowish dyes. More preferably, the yellow disperse dye composition contains 3 to 15% by weight of the orange disperse dye and 85 to 97% by weight of the yellow dye.

  Among the yellow to orange first disperse dye compositions of the present invention, the orange disperse dye composition comprises 20 to 98% by weight of the orange disperse dye represented by the formula [1] and the formula [2]. The dye represented by formula [3], the dye represented by formula [4], the dye represented by formula [5], and the dye represented by formula [6] It is preferable to contain 2 to 80% by weight of at least one yellow dye selected from: More preferably, the orange disperse dye is 25 to 85% by weight and the yellow dye is 15 to 75% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight and the yellow dye is 70%. ~ 30% by weight.

  The dye of the formula [17] is also a dye having good light resistance and can be used in the blending. By using together with the orange disperse dye represented by the formula [1], the sublimation fastness and build-up property, which are the disadvantages of the dye of the formula [17], are improved. Therefore, the second disperse dye composition of the present invention is characterized by including the orange disperse dye represented by the formula [1] and the dye represented by the formula [17].

  The orange-based second disperse dye composition of the present invention contains 20 to 98% by weight of the orange disperse dye represented by the formula [1] and 2 to 80% by weight of the dye of the formula [17]. preferable. More preferably, the orange disperse dye is 25 to 85% by weight and the dye of the formula [17] is 15 to 75% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight and the formula [17]. 17] is 70 to 30% by weight.

  Among the yellow to orange first disperse dye compositions of the present invention, an orange disperse dye composition for blending (hereinafter referred to as “first disperse orange disperse dye composition”) It can be used in combination with a red dye and a blue dye to produce a disperse dye composition for brown, amber and black. From the viewpoint of build-up property and the like, the first orange disperse dye composition for blending is represented by 65 to 98% by weight of the orange disperse dye and the dye represented by the formula [2], represented by the formula [3]. 2 to 35 at least one dye selected from the dyes represented by formula [4], the dye represented by formula [5], and the dye represented by formula [6] It is preferable to contain by weight. More preferably, the orange disperse dye is 75 to 97% by weight and the yellow dye is 3 to 25% by weight. More preferably, the orange disperse dye is 85 to 96% by weight and the yellow dye is 4%. ~ 15% by weight.

  In addition, among the orange-based second disperse dye compositions of the present invention, another orange disperse dye composition for blending (hereinafter referred to as “second orange-dispersed dye composition for blending”) It is preferable to contain 20 to 80% by weight of the orange disperse dye and 20 to 80% by weight of the dye of the formula [17]. More preferably, the orange disperse dye is 25 to 75% by weight and the dye of the formula [17] is 75 to 25% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight and the formula [17]. 17] is 70 to 30% by weight.

  In addition, among the orange-based first disperse dye compositions, when used as black for ink-jet printing inks, the yellow dye is the first dye that is represented by the formula [3]. An orange disperse dye composition for compounding 1 is preferred.

The dye represented by the formula [2], the dye represented by the formula [3], the dye represented by the formula [4], the formula represented by the first and third disperse dye compositions Of at least one yellow dye selected from the dye represented by [5] and the dye represented by formula [6], the dye represented by formula [4] and the dye represented by formula [6] Specific examples of the dye include a dye represented by the following formula [4-1], a dye represented by the formula [4-2], a dye represented by the formula [4-3], and a formula [6-1]. And dyes represented by the formula [6-2].

  The third disperse dye composition of the present invention comprises 5 to 50% by weight of the orange disperse dye or the first disperse orange disperse dye composition, a dye represented by the formula [7], and the formula At least one red selected from the dye represented by [8], the dye represented by formula [9], the dye represented by formula [10], and the dye represented by formula [11] 3 to 50% by weight of a system dye, a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], and a formula [15] It is preferable to contain 10 to 90% by weight of at least one blue dye selected from the dyes described above and the dyes represented by the formula [16]. By adjusting the mixing ratio, a highly light-resistant disperse dye composition for brown, amber, and black can be produced. Moreover, when it is going to obtain a gray dyeing | staining thing, a desired hue can be obtained by making the dyeing | staining density | concentration of the said disperse dye composition for black low. More preferably, the orange disperse dye or the first disperse orange disperse dye composition is 15 to 45% by weight, the red dye is 5 to 40% by weight, and the blue dye is 20 to 85% by weight. It is.

  In addition, among the third and fourth disperse dye compositions, when used as a black color for ink jet textile printing, the red dye is the first dye that is represented by the formula [8]. 3 and 4 disperse dye compositions are preferred.

  When the hydrophobic fiber material is dyed by the dip dyeing method or the printing method, the blue dye is represented by the dye represented by the formula [14], the dye represented by the formula [15], or the formula [16. The third and fourth disperse dye compositions using a dye represented by the formula: When used as a black ink for ink jet textile printing, the third and fourth dispersions using the dye represented by the formula [12] or the dye represented by the formula [13] as the blue dye. A dye composition is preferred.

The dye represented by the formula [7], the dye represented by the formula [8], the dye represented by the formula [9], the formula represented in the third and fourth disperse dye compositions Specific examples of the dyes represented by the formulas [8], [10] and [11] among the dyes represented by [10] and the formula [11] include the following formula [8-1]: Dye represented by the following formula [8-2], dye represented by the following formula [8-3], dye represented by the following formula [10-1], formula [10-2] ], The dye represented by the following formula [11-1], and the dye represented by the following formula [11-2].

The dye represented by the formula [12], the dye represented by the formula [13], the dye represented by the formula [14], the formula represented by the third and fourth disperse dye compositions Of the dye represented by [15] and the dye represented by formula [16], the dye represented by formula [13], the dye represented by formula [15] and the formula [16] As specific examples of the dye represented, the dye represented by the following formula [13-1], the dye represented by the following formula [15-1], the dye represented by the following formula [15-2], Examples include dyes represented by the formula [15-3], dyes represented by the following formula [16-1], and dyes represented by the following formula [16-2].

  The disperse dye composition for brown, amber or black having high light resistance will be described more specifically. The disperse dye composition for brown is represented by the formula [8], the dye represented by the formula [7], 20 to 50% by weight of the orange disperse dye or the first orange disperse dye composition for blending. 20 to 50, at least one red dye selected from the dyes represented by formula [9], the dye represented by formula [10], and the dye represented by formula [11] % By weight and a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], and the formula It is preferable to contain 10 to 50% by weight of at least one blue dye selected from the dyes represented by [16]. More preferably, the disperse dye composition for brown is 25 to 45% by weight of the orange disperse dye or the first orange disperse dye composition for blending, 25 to 40% by weight of the red dye, and the blue color. 20 to 40% by weight of a dye is contained.

  The disperse dye composition for fading is 5 to 20% by weight of the orange disperse dye or the first orange disperse dye composition for blending, the dye represented by the formula [7], and the formula [8]. A dye represented by formula [9], a dye represented by formula [10], and at least one red dye selected from the dye represented by formula [11]. 3 to 25% by weight and a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], And it is preferable to contain 60 to 90 weight% of at least 1 sort (s) of blue dye chosen from the dye represented by said Formula [16]. More preferably, the disperse dye composition for amber color is 10 to 15% by weight of the orange disperse dye or the first orange disperse dye composition for blending, 5 to 20% by weight of the red dye, and the blue color. Contains 65 to 85% by weight of a system dye.

  Further, the black disperse dye composition comprises 20 to 45% by weight of the orange disperse dye or the first disperse orange disperse dye composition, a dye represented by the formula [7], and the formula [8]. A dye represented by formula [9], a dye represented by formula [10], and at least one red dye selected from the dye represented by formula [11]. 5 to 25% by weight and a dye represented by the formula [12], a dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], And it is preferable to contain 45-70 weight% of at least 1 sort (s) of blue dye chosen from the dye represented by said Formula [16]. More preferably, the disperse dye composition for black is 25 to 40% by weight of the orange disperse dye or the first orange disperse dye composition for blending, 5 to 20% by weight of the red dye, and the blue color. Contains 50 to 65% by weight of the system dye.

  In addition, the fourth disperse dye composition of the present invention includes a second compounding orange disperse dye composition, a dye represented by the formula [7], a dye represented by the formula [8], At least one red dye selected from the dye represented by the formula [9], the dye represented by the formula [10], and the dye represented by the formula [11], and the formula [12] A dye represented by the formula [13], a dye represented by the formula [14], a dye represented by the formula [15], and a dye represented by the formula [16]. And at least one selected from the group consisting of blue dyes. The fourth disperse dye composition contains 5 to 50% by weight of the second disperse orange disperse dye composition, 3 to 50% by weight of the red dye, and 10 to 90% by weight of the blue dye. Is preferred.

  Furthermore, you may add another disperse dye to the said 1st to 4th disperse dye composition for hue adjustment in the range which does not reduce light fastness.

  A method for preparing the orange disperse dye and the dye preparation of the present invention will be described. In the dye represented by the formula [1], the dye represented by the formula [2], the dye represented by the formula [3], the dye represented by the formula [4], and the formula [5] A dye represented by the formula [6], a dye represented by the formula [7], a dye represented by the formula [8], a dye represented by the formula [9], Dye represented by Formula [10], Dye represented by Formula [11], Dye represented by Formula [12], Dye represented by Formula [13], represented by Formula [14] The dye represented by the formula [15], the dye represented by the formula [16] and the dye represented by the formula [17] are dispersed in a wet cake of the dye, for example, by a conventional method. For example, a formalin condensate of naphthalene sulfonic acid, an anionic surfactant such as lignin sulfonic acid, and water, and a sand mill, etc. It can be atomized to obtain a dispersion of the dye. The average particle diameter of the fine particles is preferably about 0.2 to 1.0 μm for dyeing and 0.5 μm or less for inkjet ink. The orange disperse dye and the dye preparation are used in the form of a dispersion obtained or a powder obtained by drying it.

  A method for preparing the first to fourth disperse dye compositions and the first and second disperse dye compositions for blending according to the present invention will be described. The first to fourth disperse dye compositions and the first and second disperse dye compositions for blending are prepared by mixing the orange disperse dye and the dye composition in the form of a dispersion or a powder obtained by drying the dispersion liquid. It is obtained by blending.

  A method for dyeing a hydrophobic fiber material using the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending will be described. First, the orange disperse dye and the disperse dye composition are each dispersed in an aqueous medium, and a dyeing bath to which a pH adjuster, a dispersion leveling agent, and the like are added as necessary is prepared. The hydrophobic fiber material is immersed in the dye bath. For example, in the case of polyester fibers, the immersion is performed under pressure, for example, at a temperature of 105 ° C. or higher, preferably 110 to 140 ° C. The dyeing bath may further contain a carrier such as o-phenylphenol, methylnaphthalene, or trichlorobenzene, and the immersion performed in the dyeing bath containing the carrier is performed at a relatively low temperature, for example, 100 ° C to 110 ° C. It can be carried out in the temperature range. Also, each of the dye dispersions in which the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending are dispersed in an aqueous medium is padded on a cloth. Further, dyeing can be performed by a steaming method at a temperature of 100 ° C. or higher, or a so-called thermosol method in which a dry heat treatment is performed. In addition, the orange disperse dye and the disperse dye composition include natural pastes (eg locust bean gum, guar gum, snow argin, casein), processed pastes (eg, fiber derivatives such as carboxymethyl cellulose, processed locust bean gum, etc. ), A synthetic paste (for example, polyvinyl alcohol, polyvinyl acetate, etc.), an anti-reducing agent, a pH adjuster, a thickening agent, etc., and preparing a printing paste, printing on the cloth using the printing paste, Dyeing by a printing method using a thermosol treatment may be performed. Furthermore, it is also possible to obtain a dyed product having excellent light resistance using an ultraviolet absorber. Although the usage-amount of the said ultraviolet absorber is not restrict | limited in particular, 0.5-5 weight% (ratio of 5-5g with respect to 100g of cloth) is preferable with respect to the weight of a to-be-dyed object, and 1-2 weight% Most preferred.

  Specific examples of the hydrophobic fiber material that can be dyed by the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions according to the present invention include ordinary disperse dyes. The dye is not particularly limited as long as it is dyed. For example, polyethylene terephthalate, polyester fiber such as polycondensate of terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane, triacetate fiber, diacetate fiber, and these Examples thereof include blended products, and natural fibers such as cotton, silk and wool or synthetic fibers such as nylon and the above-mentioned fibers, and blended fabrics.

  Moreover, as said hydrophobic fiber material, a fine denier polyester fiber is mentioned, for example. Fine denier polyester fiber is used for automobile interiors (especially for seat seat materials), and the market is expanding as consumers feel it. This is a polyester fiber with an extremely fineness [usually a fiber having a fineness of 1.0 d (denier) or less, more preferably 0.01 to 0.4 d (denier)], both a microfiber and a new synthetic fiber. be called. Even though these ultrafine fibers have the same dye exhaustion rate (build-up rate) as thick fibers, they appear pale to the human eye. preferable. Furthermore, some of the new synthetic fibers have polyesters with high crystal orientation, and such polyesters are difficult to dye. Therefore, it is preferable to use the disperse dyes of the present invention to develop dark colors.

  The ink for inkjet textile printing of the present invention contains the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending.

  The ink for inkjet textile printing according to the present invention comprises, as necessary, water, a water-soluble organic solvent, and a dispersant in the dispersion liquid of the orange disperse dye or the disperse dye composition finely divided into an average particle size of 0.5 μm or less. It is preferable to produce by adding various additives such as. The average particle size is more preferably 0.05 to 0.2 μm from the viewpoint of preventing nozzle clogging and the like.

  In general, the content of the dye is preferably 0.5 to 15% by weight with respect to the total weight of the ink because dispersion stability is maintained and a necessary print density is obtained. More preferably, the content of the dye is 1 to 12% by weight.

  Examples of the water-soluble organic solvent used in the present invention include ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, thiodiglycol, glycerin, and diglycerin. Polyhydric alcohols, glycol ethers such as ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, alcohols such as isopropyl alcohol, methanol, ethanol, benzyl alcohol, N- Salts such as methyl-2-pyrrolidone and triethanolamine It includes sexual solvent.

  Of the water-soluble organic solvents, glycerin, diethylene glycol, polyethylene glycol 300, 400, and propylene glycol are preferable. In particular, glycerin is preferred as a humectant.

  These water-soluble organic solvents may be used alone or in combination of two or more.

  The content of these water-soluble organic solvents is preferably 5 to 50% by weight with respect to the total weight of the ink from the viewpoint of adjusting the viscosity of the ink and preventing clogging due to the moisturizing effect. The content of the water-soluble organic solvent is more preferably 10 to 45% by weight, particularly preferably 15 to 40% by weight, based on the total weight of the ink.

  The dispersant used in the present invention is for dispersing the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending in an aqueous medium. Although it does not limit, it is an anionic surfactant and a nonionic surfactant, for example, and an anionic surfactant is preferable.

  Examples of the anionic surfactant include formalin condensate of naphthalene sulfonate, lignin sulfonate, formalin condensate of special aromatic sulfonate, formalin condensate of creosote oil sulfonate, polyoxyethylene alkyl Examples include ether sulfates.

  Examples of the nonionic surfactant include polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene derivative, oxyethylene / oxypropylene block copolymer, and the like.

  The content of these dispersants is determined in order to maintain good dispersion stability of the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions. 0.5-20 weight% is preferable with respect to the total weight. The content of the dispersant is more preferably 0.5 to 10% by weight, and particularly preferably 0.5 to 5% by weight.

An ink for inkjet recording having good redispersibility by further containing a compound represented by the following formula (I) (wherein R represents an alkyl group having 25 to 50 carbon atoms, and n represents 10 to 100). A composition can be obtained. In the following formula (I), R is preferably an alkyl group having 30 to 50 carbon atoms, and has 30 to 35 carbon atoms from the viewpoint of continuous ejection stability, ejection properties after standing for a long time, and long-term storage stability. An alkyl group is more preferred. In following formula (I), n becomes like this. Preferably it is 20-100, More preferably, it is 30-100. The alkyl group may be linear or branched, but is preferably a linear alkyl group.
R—O— (CH ₂ CH ₂ O) _n —H (I)

  The HLB of this compound (I) is, for example, 10 or more from the viewpoint of solubility in water. The HLB is preferably 14-18.

  The compound of the formula (I) is preferably used in an amount of 0.1 to 8% by weight, more preferably 0.1 to 6% by weight, still more preferably 0.2 to 4% by weight, based on the total amount of the ink. By using the compound of the formula (I) in the range of 0.1 to 8% by weight, there is no problem that the added amount is too high and the viscosity of the ink becomes too high, and the effect of improving the redispersibility can be exhibited. It is preferable.

  Examples of the compound of the formula (I) include “Unitox 450” (R is a linear alkyl group having 30 carbon atoms, n is about 10, HLB = 10), “Unitox 480” R is a linear alkyl group having 30 carbon atoms, n is about 40, HLB = 16), “Unitox 490” (R is a linear alkyl group having 30 carbon atoms, n is about 94, HLB = 18), “ “Unitox 550” (R is a linear alkyl group having 40 carbon atoms, n is about 12, HLB = 10), “Unitox 750” (R is a linear alkyl group having 50 carbon atoms, n is about 16, and HLB = 10). Among these, “Unitox 480” and “Unitox 490” are preferable as the compound of the formula (I).

  When the compound of the formula (I) is added, it is preferably added in the form of an aqueous solution of the compound of the formula (I) of about 5 to 15% by weight from the viewpoint of workability.

  Various other additives can be added to the ink of the present invention as necessary within a range not impeding the achievement of the object of the present invention. Other various additives are, for example, surface conditioners, hydrotropes, pH adjusters, viscosity adjusters, preservatives, fungicides, light stabilizers, chelating agents, antifoaming agents, and the like.

  Among the above additives, examples of the surface conditioner include fluorine-based surfactants, polyether-modified polydimethylsiloxane, and acrylic polymers, and polyether-modified polydimethylsiloxane and acrylic polymers are particularly preferable. . These surface conditioners are effective in adjusting the surface tension of the ink and making the ink easy to get wet with the ink flow path system material. The surface conditioner is used in a range of 0.05 to 1% by weight, preferably 0.1 to 0.5% by weight, based on the total weight of the ink. This is because when the surface conditioning agent is used in an amount of 0.05% by weight or more based on the total weight of the ink, the surface conditioning effect is enhanced, and when it is used at 1% by weight or less, a constant high surface conditioning effect is obtained.

  The method for preparing the ink for inkjet recording of the present invention is not particularly limited, but it is preferably prepared by the method described below. That is, first, (a) each of the dyes used in the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions, a dispersant, water, and the necessity Depending on the conditions, a water-soluble organic solvent and the additives can be mixed and stirred to prepare a preliminary dispersion. Next, (b) the preliminary dispersion can be dispersed with a wet medium mill such as a sand mill to obtain a dispersion of each dye. (C) When preparing an ink containing only the orange disperse dye, the concentration is adjusted by adding water, a water-soluble organic solvent, and, if necessary, the additive to the dispersion, and then filtering it with a filter paper. can do. When preparing the first to fourth disperse dye compositions and the first and second disperse dye composition inks, predetermined amounts of the respective dispersion liquids are mixed, and the mixed dispersion liquid is prepared. In addition, after adjusting the concentration by adding water, a water-soluble organic solvent, and, if necessary, the additive, it may be used after being filtered with a filter paper or the like.

  In the steps (a) and (b), when preparing inks of the first to fourth disperse dye compositions and the first and second disperse dye compositions, the respective dyes for blending are prepared. After mixing, it is dispersed together with a dispersant to obtain a dispersion, and water, a water-soluble organic solvent, a dispersion of the first to fourth disperse dye compositions and the first and second disperse dye compositions for blending, If necessary, the additive may be added to adjust the concentration.

  The average particle size of the disperse dye obtained by the above method is preferably 0.5 μm or less, more preferably 0.05 to 0.2 μm.

  As mentioned above, although illustrated about the solvent, the coloring material, the dispersing agent, and other components, the present invention is not limited to this example.

  In addition, in the ink for inkjet textile printing, the dye used for blending the black ink is represented by the dye represented by the formula [1], the dye represented by the formula [2], and the formula [3]. Dye, Dye represented by Formula [4], Dye represented by Formula [5], Dye represented by Formula [6], Dye represented by Formula [7], Formula [8 ], A dye represented by the formula [9], a dye represented by the formula [10], a dye represented by the formula [11], a dye represented by the formula [12] The dye represented by the formula [13], the dye represented by the formula [14], the dye represented by the formula [15], the dye represented by the formula [16], and the formula [17]. Among the dyes represented by formula (1), the orange disperse dye represented by the formula [1] and the yellow dye are represented by the formula [3]. Dyes, dye as the red dye represented by the formula [8], the dye as the blue dye represented by the dye and the formula [13] represented by the formula [12] particularly preferable.

  In addition, printing with ink for inkjet printing can be performed, for example, as follows. First, the ink for ink-jet textile printing can be set in a piezo-type ink-jet printer and ejected onto a polyester cloth that has been subjected to pretreatment such as bleeding prevention to form a desired image. Furthermore, this cloth is heat-treated at a temperature of, for example, 150 to 220 ° C., and the disperse dye is dyed into polyester fibers. Thereafter, unfixed disperse dye, additives such as a dispersant, pretreatment agent and the like are removed by reduction washing and water washing, and dried to obtain a dyed product of the image.

  Hereinafter, the present invention will be described more specifically with reference to examples, but the embodiments of the present invention are not limited thereto. In the following examples, “part” means “part by weight” unless otherwise specified, and “%” means “% by weight” unless otherwise specified.

Example 1 [Synthesis of Orange Disperse Dye [1-1]]
A mixture of N-cyanoethyl-N-hydroxyethylaniline (18.7 parts) and β-picoline (10.9 parts) was heated to 50 ° C. Thereafter, benzoyl chloride (16.8 parts) was dropped into the mixture at 60 to 70 ° C. over 3 hours, and then kept at the same temperature for 1 hour to obtain N-cyanoethyl-N-benzoyloxyethylaniline. . Sulfamic acid (2 parts) was added to this mixture, 120 parts of acetic acid was added and dissolved, and ice was added to adjust the mixture to 5 to 10 ° C. to obtain a coupler solution.

  To a mixture of concentrated sulfuric acid (50 parts) and 43% nitrosylsulfuric acid (29.2 parts) cooled to 5 ° C., 5 parts of 2-amino-3-chloro-5-nitro-1-trifluoromethylbenzene (24 parts) were added. Gradually added in the range of -10 ° C. The said mixture was kept at 5-10 degreeC for 4 hours, and the diazo compound was obtained.

  The diazo compound solution was dropped into the coupler solution over 3 hours while appropriately adding ice so that the temperature was maintained at 5 to 10 ° C., and a coupling reaction was performed.

The reaction mixture was then maintained at 5-10 ° C for 1 hour before being purged with 1000 parts of water. The obtained mixture was adjusted to pH = 4 with a 48% aqueous sodium hydroxide solution and then heated to 70 ° C. After stirring at the same temperature for 1 hour, the product was filtered off from the mixture, and the product was washed with water and dried to obtain 54.3 parts of a monoazo compound represented by the following formula [1-1]. The maximum absorption wavelength (λmax) in the acetone solution of the monoazo compound represented by the following formula [1-1] was 423 nm.

Example 2 [Synthesis of Orange Disperse Dye [1-2]]
Substituting 2-amino-3-bromo-5-nitro-1-trifluoromethylbenzene (28.5 parts) for 2-amino-3-chloro-5-nitro-1-trifluoromethylbenzene, and A dye represented by the following formula [1-2] was obtained in the same manner as in Example 1 except that N-cyanoethyl-N-cyanoethyloxyethylaniline was used instead of N-cyanoethyl-N-benzoyloxyethylaniline. . N-cyanoethyl-N-cyanoethyloxyethylaniline was produced as follows. A mixture of N-cyanoethyl-N-hydroxyethylaniline (18.7 parts) and acrylonitrile (14.9 parts) was heated to 80 to 90 ° C., and kept at the same temperature for 2 hours, so that N-cyanoethyl-N— Cyanoethyloxyethylaniline was obtained.

The maximum absorption wavelength (λmax) in the acetone solution of the obtained monoazo compound represented by the following formula [1-2] was 429 nm.

Example 3 [Synthesis of Orange Disperse Dye [1-3]]
Substituting 2-amino-3-bromo-5-nitro-1-trifluoromethylbenzene (28.5 parts) for 2-amino-3-chloro-5-nitro-1-trifluoromethylbenzene, and A dye represented by the following formula [1-3] is obtained in the same manner as in Example 1 except that N-cyanoethyl-N-butyloxyethylaniline is used instead of N-cyanoethyl-N-benzoyloxyethylaniline. It was. N-cyanoethyl-N-butyloxyethylaniline was produced as follows. A mixture of N-cyanoethylaniline (14.6 parts), magnesium hydroxide (3.6 parts) and water (18.4 parts) was heated to 70 ° C. Thereafter, p-toluenesulfonic acid n-butyl cellosolve ether (33.7 parts) was dropped into the mixture at 70 to 85 ° C. over 3 hours, and then maintained at 90 to 95 ° C. for 10 hours to obtain N-cyanoethyl-N. -Butyloxyethylaniline was obtained.

The maximum absorption wavelength (λmax) in the acetone solution of the monoazo compound represented by the following formula [1-3] was 432 nm.

Example 4 [Dye Formulation [1-1]]
30 parts of the dye represented by the formula [1-1] was finely divided by a sand mill in 35 parts of a formalin condensate of naphthalene sulfonic acid and 85 parts of water, and then 30 parts of lignin sulfonic acid was added. The mixture was spray-dried to obtain a dye formulation [1-1] comprising 30% of the dye represented by the formula [1-1], 65% of an anionic dispersant, and 5% of water.

(Example 5) [Dye preparation [1-2], [1-3] and [2] to [16]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [1-2] was used except that the dye represented by the formula [1-2] was used. 30% dye, 65% anionic dispersant A dye preparation [1-2] consisting of 5% water was obtained.

  Instead of the dye represented by the formula [1-1], a dye represented by the formula [1-3] was used except that the dye represented by the formula [1-3] was used. A dye formulation [1-3] consisting of 5% water was obtained.

  Instead of the dye represented by the formula [1-1], the dye represented by the formula [2], the dye represented by the formula [3], and the dye represented by the formula [4-1] , A dye represented by the formula [4-2], a dye represented by the formula [4-3], a dye represented by the formula [5], a dye represented by the formula [6-1] , A dye represented by the formula [6-2], a dye represented by the formula [7], a dye represented by the formula [8-1], a dye represented by the formula [8-2] , A dye represented by the formula [8-3], a dye represented by the formula [9], a dye represented by the formula [10-1], a dye represented by the formula [10-2] A dye represented by the formula [11-1], a dye represented by the formula [12], a dye represented by the formula [13-1], a dye represented by the formula [14], Dye represented by Formula [15-1] The dye represented by the formula [15-2], the dye represented by the formula [15-3], the dye represented by the formula [16-1], and the formula [16-2]. Except for using a dye, the same as in Example 4, a dye preparation [2], a dye preparation [3], and a dye preparation [4-1] comprising 30% dye, 65% anionic dispersant, and 5% moisture. ], Dye Formulation [4-2], Dye Formulation [4-3], Dye Formulation [5], Dye Formulation [6-1], Dye Formulation [6-2], Dye Formulation [7] ], Dye preparation [8-1], dye preparation [8-2], dye preparation [8-3], dye preparation [9], dye preparation [10-1], dye preparation [10 -2], Dye Formulation [11-1], Dye Formulation [12], Dye Formulation [13-1], Dye Formulation [14], Dye Formulation [15-1], Dye Formulation [15 2], dyestuff preparations [15-3] was obtained dyestuff preparations [16-1] and dyestuff preparations [16-2], respectively.

Comparative Example 1 [Dye Formulation (1), (2), (3-1), (4) and (3)]
Instead of the dye represented by the formula [1-1], the dye represented by the formula (1), the dye represented by the formula (2), and the dye represented by the following formula (3-1) In the same manner as in Example 4, except that the dye represented by the formula (4) and the dye represented by the formula (3) were used, the dye was composed of 30%, an anionic dispersant 65%, and moisture 5%. Dye preparation (1), dye preparation (2), dye preparation (3-1), dye preparation (4) and dye preparation (3) were obtained. However, the dye represented by the formula (3) is the same dye as the dye represented by the formula [17], and the formula (3) is used instead of the formula [17] in the formulation examples of the examples. .

The dye represented by the following formula (3-1) was the same as in Example 1 except that 1-methyl-2-phenylindole was used instead of N-cyanoethyl-N-benzoyloxyethylaniline. Obtained.

(Example 6) [Dyeing of regular polyester]
The dye preparation [1-1] (0.58 g) (0.174 g of dye component) and 300 cc of water were placed in a dyeing pot, and the pH of the mixture was adjusted to pH 5 using acetic acid to obtain a dyeing bath. . Next, regular polyester fabric trade name “Tropical” (manufactured by Teijin Ltd.) (15 g) was added to the dyeing bath in the dyeing pot and dyed at 130 ° C. for 40 minutes. Thereafter, the woven fabric was reduced and washed by a normal method and then dried to obtain a dyed product A [1-1]. The dyed product thus obtained was used as a dyeing cloth having a dyeing density of 1/1 N.

(Example 7)
Instead of the dye preparation [1-1], 0.58 g of the dye preparation [1-2] (0.174 g of dye) and 0.58 g of the dye preparation [1-3] (0. Except using 174g), it dye | stained similarly to Example 6, respectively, and obtained the dyeing | staining A [1-2] and the dyeing | staining A [1-3].

(Comparative Example 2)
In place of the dye preparation [1-1], the dye preparation (1) (0.58 g) (dye content 0.174 g), the dye preparation (2) (0.58 g) (dye content 0. 174 g), the dye formulation (3-1) (0.58 g) (0.174 g dye content), the dye formulation (4) (0.58 g) (0.174 g dye content) and the dye formulation ( 3) Dyeing was carried out in the same manner as in Example 6 except that (0.58 g) (dye content 0.174 g) was used, and dyeing A (1), dyeing A (2), dyeing A (3- 1) Dyeing A (4) and Dyeing A (3) were obtained.

  With respect to the dyed products obtained in Examples 6 and 7 and Comparative Example 2, the light fastness, sublimation fastness and exhaustion (build-up property) were measured, and the results are shown in Table 1. Table 1 also shows the maximum absorption wavelength (λmax) of the acetone solution of each dye used.

[Light fastness]
Light fastness was tested using a dyed cloth with a dyeing density of 1/1 N, an ultraviolet carbon arc lamp method according to JIS L 0842-1996, and an ultraviolet fade meter U48 (manufactured by Suga Test Instruments Co., Ltd.). The temperature inside the apparatus is maintained such that the temperature of a reference plate called a black panel accommodated in the apparatus is 63 ± 3 ° C., and after irradiation for 80 hours, JIS L 0804-1994 gray scale for color change Standard: ISO 105-A02).

[Sublimation fastness]
The sublimation fastness is a dyeing cloth having a dyeing density of 1/1 N, and a processing temperature of 180 ± 2 ° C. × 30 seconds according to JIS L 0879-1996 (corresponding international standard: ISO 105-P01: 1993) (attached contaminated cloth = This was carried out using Toray's polyester trade name “Tetron” and nylon.

[Exhaust (build-up)]
Exhaustability (build-up property) was determined visually by comparing the density of dyed cloth with dyeing densities of 1 / 2N, 1 / 1N, and 2 / 1N. ◎ means “very good”, ◯ means “good”, Δ means “somewhat inferior”, and x means “inferior”.

  As is apparent from Table 1, in the dyed product using the regular polyester cloth, the orange disperse dye represented by the formula [1] of the present invention has a light fastness of 4-5 and a sublimation fastness of 3- It was grade 4 or higher, had good build-up properties, and was excellent in light resistance, sublimation fastness and build-up properties. On the other hand, the dye represented by the formula (1) and the dye represented by the formula (2) of the comparative example were excellent in sublimation fastness and build-up property, but had a light resistance of 4th grade and the orange disperse dye of the present invention. It was a little inferior. In addition, the dye represented by the formula (3-1) is excellent in light resistance, which is equivalent to the orange disperse dye of the present invention, but the sublimation fastness is inferior to the second grade, and the build-up property is not good. It was. Moreover, about the dye represented by the said Formula (4), although light resistance and buildup property were excellent, the sublimation fastness was inferior to the 3rd grade. Further, the dye represented by the formula (3) has very good light resistance, but its sublimation fastness is inferior to the third grade, and the build-up property is not good.

  Further, the orange disperse dye of the present invention has a λmax higher than that of the dye represented by the formula (1), the dye represented by the formula (2), the dye represented by the formula (3-1), and the dye represented by the formula (3). As can be seen from the longer wavelength side, it had a slightly reddish hue.

(Example 8) [Dyeing of fine denier polyester fiber]
The dye formulation [1-1] (0.28 g) (0.084 g of dye component) and 300 cc of water were placed in a dyeing pot, and the pH of the mixture was adjusted to pH 5 using acetic acid to obtain a dyeing bath. Next, a new synthetic fiber (fine denier polyester fiber) (15 g) having a fineness of 0.3 denier was charged into the dyeing bath in the dyeing pot and dyed at 130 ° C. for 40 minutes. Thereafter, the new synthetic fiber was reduced and washed by a usual method, and then dried to obtain an orange dyed product B [1-1].

Example 9
Instead of the dye preparation [1-1], the dye preparation [1-2] (0.28 g) (0.084 g dye content) and the dye preparation [1-3] (0.28 g) ( Dyeing was performed in the same manner as in Example 8 except that 0.084 g) of the dye content was used, and Dyeing B [1-2] and Dyeing B [1-3] were obtained.

(Comparative Example 3)
Instead of the dye preparation [1-1], the dye preparation (1) (0.28 g) (0.084 g of dye component), the dye preparation (2) (0.28 g) (dye component of 0.1%). 084 g), the dye preparation (3-1) (0.28 g) (0.084 g dye content), the dye preparation (4) (0.28 g) (0.084 g dye content) and the dye preparation ( 3) Dyeing was carried out in the same manner as in Example 8 except that (0.28 g) (0.084 g of dye component) was used, and dyeing B (1), dyeing B (2), dyeing B (3- 1) Dyeing B (4) and Dyeing B (3) were obtained.

(Example 10)
New synthetic fiber in the same manner as in Example 8 except that benzotriazole ultraviolet absorber Sunlife LPS-950 (manufactured by Nikka Chemical Co., Ltd.) (0.30 g) is added to the dyeing bath in the dyeing pot. (Fine denier polyester fiber) (15 g) was dyed to obtain an orange dyed product C [1-1].

(Example 11)
Instead of the dye preparation [1-1], the dye preparation [1-2] and the dye preparation [1-3] were used, respectively, in the same manner as in Example 10 to obtain a dyed product C [1- 2] and dyed product C [1-3] were obtained.

(Comparative Example 4)
In place of the dye preparation [1-1], the dye preparations (1), (2), (3-1), (4) and (3) were used for dyeing in the same manner as in Example 10. , Dyed product C (1), dyed product C (2), dyed product C (3-1), dyed product C (4) and dyed product C (3) were obtained.

The light fastness was measured for the dyed articles B and C obtained in Examples 8 to 11 and Comparative Examples 3 and 4. The light fastness was determined based on the Toyota method, which is a test method more severe than JIS L 0842. Specifically, the light fastness is a xenon weather meter (black panel temperature 73 ± 3 ° C., irradiance 150 W / m ² , Super Xenon Weather Meter, manufactured by Suga Test Instruments Co. After irradiating 38 cycles of light and dark using SC750), it was determined with a gray scale for JIS L 0804 color change.

The above-mentioned Toyota method used for measuring the light fastness is a test standard of Toyota Motor Corporation, which uses xenon arc (xenon lamp) as a light source, and tests fibers and plastics. Usually, a test device called a xenon weather meter is used for the test. Here, the irradiation intensity of the light source was set to 150 W / m ² (wavelength 300 to 400 nm), and the irradiation method was performed by repeating the light and dark method, that is, irradiating for a predetermined time and then darkening for a predetermined time. Specifically, 38 cycles (about 182 hours) were performed with an irradiation time of 3.8 hours and a dark time of 1 hour as one cycle. The humidity (in the test atmosphere) in the test apparatus was kept at 50 ± 5% during irradiation and 95 ± 5% during the dark time. The temperature in the test apparatus was maintained so that the temperature of a reference plate called a black panel accommodated in the apparatus was 73 ± 3 ° C. The test cloth (fiber) accommodated in the apparatus to be tested was lined with urethane.

The light fastness measured by the above method for the dyed articles B and C obtained in Examples 8 to 11 and Comparative Examples 3 and 4 is as follows. For dyeing B [1-1] ^{4 +,} 4 for dyeing B [1-2], 4 for dyeing B [1-3], 4-5 for dyeing C [1-1] , ^{4 +} for dyeings C [1-2], dyeings ^{4 +} for C [1-3], the dyeings B (1) for 3, dyeings B (2) for 3-4 staining object B (3-1) for ^{4 +,} dyeings B (4) for 3-4 dyeings ^{4 +} for B (3), the dyeings C (1) for 3-4 dyeings C It was 3-4 for (2), 4-5 for dyed product (3-1), 4 for dyed product (4), and 4-5 for dyed product C (3). The results are also shown in Table 2 below.

  As is clear from Table 2, in the light resistance test of the dyed product using the fine denier polyester fiber by the Toyota method, the light fastness of the orange disperse dye represented by the formula [1] of the present invention is 4th or higher. In particular, the dye represented by the formula [1-1] was very excellent in light resistance. On the other hand, with respect to the dye represented by the formula (1) and the dye represented by the formula (2), the light fastness was slightly inferior to 3-4 grade or less, and the effect of the ultraviolet absorber was also small. Moreover, about the dye represented by the said Formula (3-1) and the dye represented by the said Formula (3), light resistance was very excellent. The dye represented by the formula (4) was slightly inferior in light resistance to the dye of the present invention.

  Therefore, as is clear from Table 1 and Table 2, the orange disperse dye of the present invention is excellent in light resistance, sublimation fastness and build-up property, and the dye represented by the formula [1-1] is particularly Light resistance was excellent. On the other hand, the dye represented by the formula (1) and the dye represented by the formula (2) were excellent in sublimation fastness and build-up property, but the light resistance was inferior to the orange disperse dye of the present invention. This was particularly noticeable in the case of the Toyota Law. Further, the dye represented by the formula (3-1) and the dye represented by the formula (3) are very excellent in light resistance, but are inferior in sublimation fastness and good in build-up property. There wasn't. In addition, the dye represented by the formula (4) has excellent build-up property, but is inferior in sublimation fastness and inferior in light fastness using the Toyota method.

(Example 12)
The dye preparation [1-1], the dye preparation [1-2], the dye preparation [1-3], the dye preparation [2], the dye preparation [3], and the dye preparation [4- 1], Dye Formula [4-2], Dye Formula [4-3], Dye Formula [5], Dye Formula [6-1], Dye Formula [6-2], Dye Formula [ 7], Dye Formula [8-1], Dye Formula [8-2], Dye Formula [8-3], Dye Formula [9], Dye Formula [10-1], Dye Formula [ 10-2], dye preparation [11-1], dye preparation [12], dye preparation [13-1], dye preparation [14], dye preparation [15-1], dye preparation [ 15-2], Dye Formulation [15-3], Dye Formulation [16-1], Dye Formulation [16-2] and the Dye Formulation (3) are shown in Tables 3 to 5 below. In proportion (parts by weight) Combined and were prepared disperse dye composition 1-26.

Each dye preparation (0.28 g) (dye content 0.084 g), water (300 cc), and benzotriazole ultraviolet absorber Sun Life LPS-950 (manufactured by Nikka Chemical Co., Ltd.) (0.30 g) And the pH of the mixture was adjusted to pH 5 with acetic acid to obtain a dyeing bath. Next, 15 g of the new synthetic fiber fabric (fine denier polyester fiber) used in Example 8 was put into the dyeing bath in the dyeing pot and dyed at 130 ° C. for 40 minutes. Thereafter, the new synthetic fiber fabric was subjected to reduction cleaning by a usual method and then dried to obtain dyed products D. About the obtained dyeing | staining thing D, when the light fastness was measured like the case of the dyeing | staining B and C, the favorable light fastness was shown.

  A method for preparing ink for inkjet textile printing will be described below.

(Example 13)
[Preparation of Ink Dispersion [1-1]]
Dye (20 parts) represented by the formula [1-1], a formalin condensate of a special aromatic sodium sulfonate as an anionic surfactant as a dispersant (trade name “Demol SNB” manufactured by Kao Corporation) (10 parts), “Unitox 480” (manufactured by Petrolite, USA, R is a linear alkyl group having 30 carbon atoms, n is about 40, and HLB corresponds to 16). Part) and water (127 parts), using a 0.4 mm diameter zircon bead (330 parts) and finely pulverizing for 35 hours with a sand mill, a dispersion for ink having a dye concentration of 12.5% [ 1-1] was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [1-2]]
In the case of the dispersion liquid for ink [1-1] except that the dye represented by the formula [1-2] (20 parts) is used instead of the dye represented by the formula [1-1] Similarly, an ink dispersion [1-2] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [3]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [3] (20 parts) was used except that the same as in the case of the ink dispersion [1-1]. Thus, an ink dispersion [3] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [4-3]]
In the case of the dispersion liquid for ink [1-1] except that the dye represented by the formula [4-3] (20 parts) is used instead of the dye represented by the formula [1-1] Similarly, an ink dispersion [4-3] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [5]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [5] (20 parts) was used except that the same as in the case of the ink dispersion [1-1]. Thus, an ink dispersion [5] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [8-3]]
In the case of the dispersion liquid for ink [1-1], in place of the dye represented by the formula [1-1], a dye represented by the formula [8-3] (20 parts) is used. Similarly, an ink dispersion [8-3] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [12]]
Instead of the dye represented by the formula [1-1], a dye represented by the formula [12] (20 parts) was used except that the same as in the case of the ink dispersion [1-1]. Thus, an ink dispersion [12] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

[Preparation of Ink Dispersion [13-1]]
In the case of the dispersion liquid for ink [1-1], except that the dye represented by the formula [13-1] (20 parts) is used instead of the dye represented by the formula [1-1], Similarly, an ink dispersion [13-1] having a dye concentration of 12.5% was obtained. The average particle size of the dye was 0.10 μm.

(Example 14)
Examples of black ink will be described below, and the blending ratio is shown in Table 6.
[Preparation of black ink [27]]
Glycerin as a water-soluble organic solvent in a mixture of the ink dispersion [1-1] (56 parts), the ink dispersion [12] (84 parts) and the ink dispersion [13-1] (84 parts) (100 parts) and polyether-modified polydimethylsiloxane (manufactured by BYK Japan Japan Co., Ltd., trade name “BYK-348”) (1.0 part) as a surface conditioner (1.0 part) was added, and water was added thereto to make a total amount of 400 As a part, an ink having a dye concentration adjusted to 7% was prepared. The weight ratio of each dye is as follows: Dye represented by formula [1-1]: Dye represented by formula [12]: Dye represented by formula [13-1] = 25: 37.5: 37.5 Met.

[Preparation of black ink [28]]
Ink dispersion liquid [1-2] (40 parts), Ink dispersion liquid [3] (18 parts), Ink dispersion liquid [8-3] (11 parts), Ink dispersion liquid [12] (67 parts) ) And dispersion liquid [13-1] (88 parts) for ink, glycerin (100 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) as a surface conditioner. ) (1.0 part) was added, and water was added thereto to prepare an ink having a total amount of 400 parts and a dye concentration adjusted to 7%. The weight ratio of each dye is the dye represented by the formula [1-2]: the dye represented by the formula [3]: the dye represented by the formula [8-3]: the dye represented by the formula [12]. : Dye represented by formula [13-1] = 18: 8: 5: 30: 39.

(Example 15)
Examples of orange ink will be described below, and the blending ratio is shown in Table 7.
[Preparation of orange ink [29]]
A 10% aqueous solution of a trade name “Demol SNB” (manufactured by Kao Corporation) as a dispersant in a mixture of the ink dispersion [1-1] (101 parts) and the ink dispersion [3] (43 parts). (40 parts), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) (1.0 part) as a surface conditioner are added, and water is added thereto. In addition, an ink was prepared in which the total amount was 400 parts and the dye concentration was adjusted to 4.5%. The weight ratio of each dye was the dye represented by the formula [1-1]: the dye represented by the formula [3] = 70: 30.

[Preparation of orange ink [30]]
In the mixed liquid of the ink dispersion [1-1] (94 parts) and the ink dispersion [4-3] (50 parts), 10 of the trade name “Demol SNB” (manufactured by Kao Corporation) as a dispersant. % Aqueous solution (40 parts), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by BYK Japan KK) (1.0 part) as a surface conditioner, there Water was added to make a total amount of 400 parts, and an ink having a dye concentration adjusted to 4.5% was prepared. The weight ratio of each dye was the dye represented by the formula [1-1]: the dye represented by the formula [4-3] = 65: 35.

[Preparation of orange ink [31]]
A 10% aqueous solution (40) of “Demol SNB” (manufactured by Kao Corporation) as a dispersant in a mixture of the ink dispersion [1-1] (101 parts) and the ink dispersion [5] (43 parts). Part), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) (1.0 part) as a surface conditioner, and water is added to the whole amount. Ink was prepared by adjusting the dye concentration to 4.5%. The weight ratio of each dye was the dye represented by the formula [1-1]: the dye represented by the formula [5] = 70: 30.

[Preparation of orange ink [32]]
A 10% aqueous solution of “Demol SNB” (manufactured by Kao Corporation) as a dispersant in a mixture of the ink dispersion [1-1] (89 parts) and the ink dispersion [6-1] (55 parts). (40 parts), glycerin (110 parts) as a water-soluble organic solvent, and trade name “BYK-348” (manufactured by Big Chemie Japan Co., Ltd.) (1.0 part) as a surface conditioner are added, and water is added thereto. In addition, an ink was prepared in which the total amount was 400 parts and the dye concentration was adjusted to 4.5%. The weight ratio of each dye was dye represented by formula [1-1]: dye represented by formula [6-1] = 62: 38.

Example 16 [Dyeing with Inkjet Textile Ink]
Ink-jet textile printing inks [27] to [32] are individually set in a piezo-type ink jet printer and printed on a regular polyester cloth of 1500 mm width × 10 m length subjected to pretreatment such as bleeding prevention, with a printing resolution of 360 × 360 dpi. A single color / filled print was performed. As a result, any of the inkjet printing inks [27] to [32] exhibited good ejection stability without causing clogging. Further, the polyester cloth was dried and then heat-treated in superheated steam at 175 ° C. for 7 minutes to dye the polyester cloth. Unfixed dyes, additives such as dispersants, pretreatment agents and the like were removed by reduction washing and water washing, and dried to obtain a dyed product E of each hue. When the light fastness of the obtained dyed product E was measured based on the Toyota method, all showed good light fastness.

Claims (17)

An orange disperse dye represented by the following formula [1] and having an orange color.

[In the formula [1], X ₁ represents a chlorine atom or a bromine atom, and R ₁ is substituted with one or more of a benzoyl group, a cyanoethyl group, a C ₁ -C ₄ alkyl group, a phenyl group, or a C ₁ -C ₄ alkyl. Represents a phenyl group. ] An orange disperse dye represented by the formula [1] of claim 1;
Dye represented by the following formula [2], dye represented by the following formula [3], dye represented by the following formula [4], dye represented by the following formula [5], and formula [6] And at least one yellow dye selected from the dyes represented by
A disperse dye composition characterized by being yellow to orange.

[In the above formula [4], _{X 2} represents a hydrogen atom or a bromine atom, _{R 2} represents a hydrogen atom or -COOC ₂ H ₄ OC ₂ H ₅ group. ]

[In the above formula [6], R ₃ represents a C ₁ -C ₄ alkyl group, a phenyl group, or a phenyl group substituted with one or more C ₁ -C ₄ alkyl. ]   3. The disperse dye composition according to claim 2, comprising 3 to 20 wt% of the orange disperse dye and 80 to 97 wt% of the yellow dye, and having a yellow color.   3. The disperse dye composition according to claim 2, comprising 20 to 98 wt% of the orange disperse dye and 2 to 80 wt% of the yellow dye and having an orange color.   The disperse dye composition according to claim 2, wherein the disperse dye composition contains 65 to 98% by weight of the orange disperse dye and 2 to 35% by weight of the yellow dye, is orange, and is used for blending. A disperse dye composition comprising the orange disperse dye represented by the formula [1] according to claim 1 and a dye represented by the following formula [17].

  The disperse dye composition according to claim 6, wherein the disperse dye composition contains 20 to 98% by weight of the orange disperse dye and 2 to 80% by weight of the dye represented by the formula [17], and is orange.   The disperse dye composition according to claim 6, wherein the disperse dye composition contains 20 to 80% by weight of the orange disperse dye and 20 to 80% by weight of the dye represented by the formula [17], is orange, and is used for blending. The orange disperse dye according to claim 1 or the disperse dye composition according to claim 5,
Dye represented by the following formula [7], dye represented by the following formula [8], dye represented by the following formula [9], dye represented by the following formula [10], and formula [11] At least one red dye selected from the dyes represented by:
Dye represented by the following formula [12], dye represented by the following formula [13], dye represented by the following formula [14], dye represented by the following formula [15], and formula [16] A disperse dye composition comprising at least one blue dye selected from the dyes represented by formula (1).

[Representing the formula [8] in, _{R 4} is a hydrogen atom, -OCH ₃ group, _-OC 2 _{H 5} group, or _{-SO 2 NHC 3 H 6 OC 2} H 5 group. ]

[Representing the formula [10] in, _{R 5} is a substituted or unsubstituted phenyl group, -COOC ₂ H ₅ group, or -COOC ₆ H ₅ group. ]

[In the above formula [11], _{R 6} represents a hydrogen atom, -CH ₃ group or _-C 2 _{H 5} group. ]

[Representing the formula [13] in, _{R 7} is _{-C 3 H} 6 OCH 3 group or _{-C 3 H 6 OC 2 H 4} OCH 3 group. ]

[In the formula [15], _{R 8} represents a hydroxyl group, -OCH ₃ group or _-OC 2 _{H 5} group. ]

[In the formula [16], _{X 3} represents a hydrogen atom or a bromine atom. ] 5 to 50% by weight of the orange disperse dye according to claim 1 or the disperse dye composition according to claim 5.
The disperse dye composition according to claim 9, comprising 3 to 50% by weight of the red dye and 10 to 90% by weight of the blue dye. A disperse dye composition according to claim 8;
Dye represented by the following formula [7], dye represented by the following formula [8], dye represented by the following formula [9], dye represented by the following formula [10], and formula [11] At least one red dye selected from the dyes represented by:
Dye represented by the following formula [12], dye represented by the following formula [13], dye represented by the following formula [14], dye represented by the following formula [15], and formula [16] A disperse dye composition comprising at least one blue dye selected from the dyes represented by formula (1).

[Representing the formula [8] in, _{R 4} is a hydrogen atom, -OCH ₃ group, _-OC 2 _{H 5} group, or _{-SO 2 NHC 3 H 6 OC 2} H 5 group. ]

[In the above formula [10], R ₅ represents a phenyl group, a phenyl group substituted with one or more C _{1 to} C ₄ alkyl, a —COOC ₂ H ₅ group or a —COOC ₆ H ₅ group. ]

[In the above formula [11], _{R 6} represents a hydrogen atom, -CH ₃ group or _-C 2 _{H 5} group. ]

[Representing the formula [13] in, _{R 7} is _{-C 3 H} 6 OCH 3 group or _{-C 3 H 6 OC 2 H 4} OCH 3 group. ]

[In the formula [15], R ₈ represents a hydroxyl group, —OCH ₃ group or —OC ₂ H ₅ group. ]

[In the formula [16], _{X 3} represents a hydrogen atom or a bromine atom. ]   The disperse dye composition according to claim 11, comprising 5 to 50% by weight of the disperse dye composition according to claim 8, 3 to 50% by weight of the red dye, and 10 to 90% by weight of the blue dye. .   A dyeing method for dyeing a hydrophobic fiber material using the orange disperse dye according to claim 1 or the disperse dye composition according to any one of claims 2 to 12.   A dyed product obtained by dyeing a hydrophobic fiber material using the orange disperse dye according to claim 1 or the disperse dye composition according to any one of claims 2 to 12.   An ink for inkjet printing comprising the orange disperse dye according to claim 1 or the disperse dye composition according to any one of claims 2 to 12.   A dyeing method for dyeing a hydrophobic fiber material using the ink for ink-jet textile printing according to claim 15.   A dyed product obtained by dyeing a hydrophobic fiber material with the ink for inkjet printing according to claim 15.