JP5917517B2 - Disperse dye composition and method for dyeing hydrophobic fiber material using the same - Google Patents

Disperse dye composition and method for dyeing hydrophobic fiber material using the same Download PDF

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JP5917517B2
JP5917517B2 JP2013526891A JP2013526891A JP5917517B2 JP 5917517 B2 JP5917517 B2 JP 5917517B2 JP 2013526891 A JP2013526891 A JP 2013526891A JP 2013526891 A JP2013526891 A JP 2013526891A JP 5917517 B2 JP5917517 B2 JP 5917517B2
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disperse dye
dyeing
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dye composition
disperse
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JPWO2013018713A1 (en
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博満 徳山
博満 徳山
山口　徹
徹 山口
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Nippon Kayaku Co Ltd
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/20—Anthraquinone dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/22—Dyes with unsubstituted amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
    • C09B1/542—Anthraquinones with aliphatic, cycloaliphatic, araliphatic or aromatic ether groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/2409—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62
    • C09B5/2436—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62 only nitrogen-containing hetero rings
    • C09B5/2445—Phtaloyl isoindoles
    • C09B5/2454—5,6 phtaloyl dihydro isoindoles
    • C09B5/2463—1,3 oxo or imino derivatives
    • C09B5/2472—1,3 dioxo derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs

Description

本発明は、分散染料組成物およびそれを用いる染色法に関する。さらに詳しくは、特定の分散染料を含有した分散染料組成物およびそれを用いる疎水性繊維材料の染色法に関する。   The present invention relates to a disperse dye composition and a dyeing method using the same. More specifically, the present invention relates to a disperse dye composition containing a specific disperse dye and a method for dyeing a hydrophobic fiber material using the same.

自動車内装材料に用いられる合成繊維材料は、自動車内が高温多湿になることや太陽光に露光される時間が他の一般衣料繊維材料に較べ格段に長いため、強い耐温度性や耐光性を要求される。これを解決するために耐光性の強い染料を用いて繊維を染色する方法がとられている。しかし、黄色系染料、赤色系染料、青色系染料の各々の耐光性のバランスが違っていると長時間の露光により一部の色だけが退色を起こす結果、これらの染料による染色物の変色が、時間の経過により次第に大きく見えるようになるという事態が生じやすい。このため使用される黄色系染料、赤色系染料、青色系染料には同じように退色してゆくバランスの取れた耐光性が要求されるが、そのような染料は得られていない。   Synthetic fiber materials used for automobile interior materials require strong temperature resistance and light resistance because the interior of automobiles is hot and humid and the exposure time to sunlight is much longer than other general clothing fiber materials. Is done. In order to solve this problem, a method of dyeing fibers using a dye having strong light resistance has been taken. However, if the balance of lightfastness of each of the yellow dye, red dye and blue dye is different, only a part of the color will fade due to long exposure. It is likely that the situation will gradually increase with time. For this reason, the yellow dye, the red dye, and the blue dye to be used are required to have a balanced light resistance that fades in the same manner, but such a dye has not been obtained.

また、合成繊維材料の糸の太さや糸の形状の違い、使われるポリエステル繊維に他の材料を混紡した混紡繊維等の違いにより、同じ染色法においても染色濃度、染色色調等が異なってくる。このように形状、性質の異なる合成繊維材料を毎回、同じように染色加工するために、各種染色条件でも染色再現性にすぐれた染料が要求されている。特に自動車内装材料の染色には、出来るだけその環境条件に対し堅牢度の強い分散染料を使用して染色を行う必要がある。しかし同時に染色特性が揃っていないと、染色された合成繊維材料の染色再現性に違いが出てきてしまう。   Further, due to the difference in the thickness of the synthetic fiber material, the shape of the yarn, the blended fiber in which other materials are blended with the polyester fiber to be used, the dyeing density, the color tone, and the like are different even in the same dyeing method. Thus, in order to dye the synthetic fiber materials having different shapes and properties in the same manner, dyes having excellent dye reproducibility are required under various dyeing conditions. In particular, for dyeing automobile interior materials, it is necessary to dye using a disperse dye having a fastness to the environmental conditions as much as possible. However, if the dyeing characteristics are not uniform at the same time, the dyeing reproducibility of the dyed synthetic fiber material will be different.

一方、近年エネルギー消費の節減が唱えられ、染色における作業工程においてもエネルギー使用量の削減、即ち染色温度や時間の低減が求められている。現在、合成繊維材料の中で最も多く使用されているポリエステル繊維を染色するには分散染料が用いられ、通常１００℃以上の温度にて染色が行われる。しかし、ポリエステル繊維等をバランス良く均一に染色するためには１３０℃以上にする必要があり、多くのエネルギーを消費することになる。この染色温度を少しでも下げられれば大きな省エネルギーにつながる。   On the other hand, in recent years, reduction of energy consumption has been advocated, and reduction of energy consumption, that is, reduction of dyeing temperature and time is also demanded in the work process in dyeing. At present, disperse dyes are used to dye the most frequently used polyester fibers among synthetic fiber materials, and dyeing is usually performed at a temperature of 100 ° C. or higher. However, in order to dye polyester fibers or the like in a well-balanced and uniform manner, it is necessary to set the temperature to 130 ° C. or more, which consumes a lot of energy. If this dyeing temperature can be lowered as much as possible, it will lead to significant energy savings.

そこで、黄色系染料、赤色系染料、青色系染料の各色の耐光堅牢度が強くかつ揃っており、さらに、温度を下げて染色しても染色時の再現性が良い分散染料組成物と染色法が求められている。しかし、以下の特許文献１〜３を含む先行技術文献には、各種の分散染料組成物が開示されているものの、前記のような要求を満足する染料組成物は記載されていない。 Therefore, disperse dye compositions and dyeing methods that have strong and uniform light fastness for each color of yellow dyes, red dyes, and blue dyes, and have good reproducibility at dyeing even when dyed at a lower temperature. Is required. However, although various disperse dye compositions are disclosed in prior art documents including the following Patent Documents 1 to 3, a dye composition that satisfies the above requirements is not described.

特開２００５−２３２５４号公報JP-A-2005-23254 特開２００４−１６８９５０号公報JP 2004-168950 A 国際公開第２００７／０５８２０９号パンフレットInternational Publication No. 2007/058209 Pamphlet

従って、本発明の目的は、黄色系染料、赤色系染料、青色系染料の各色の耐光堅牢度が強くかつ揃っており、さらに、温度を下げて染色しても染色時の再現性が良い分散染料組成物と染色法を提供することである。   Therefore, the object of the present invention is to provide a strong and uniform light fastness for each color of yellow dyes, red dyes, and blue dyes. It is to provide a dye composition and a dyeing method.

前記目的は、以下に規定される本発明によって達成される。
本発明者等は、前記課題を解決すべく鋭意研究の結果、下記の特定の各種分散染料を組みあわせることによって、三原色の分散染料が強くバランスの良い耐光堅牢度を持ち、かつ、染色時の染色温度を下げても染色特性が揃い再現性に優れた分散染料組成物、ならびにそれを用いた染色法を見出して、本発明を完成させるに至った。Said object is achieved by the invention as defined below.
As a result of diligent research to solve the above problems, the present inventors have combined the following specific disperse dyes, so that the disperse dyes of the three primary colors have a strong and well balanced light fastness, and at the time of dyeing The present invention has been completed by finding a disperse dye composition having excellent dyeing characteristics and excellent reproducibility even when the dyeing temperature is lowered, and a dyeing method using the same.

即ち、本発明の態様は、以下のとおりである。
［１］．下記式（１）で示される黄色系分散染料、および下記式（２）で示される黄色系分散染料を含む黄色系分散染料組成物、
下記式（３）で示される赤色系分散染料、および下記式（４）で示される赤色系分散染料を含む赤色系分散染料組成物、ならびに
下記式（５）で示される青色系分散染料、および下記式（６）で示される青色系分散染料を含む青色系分散染料組成物
を含有する分散染料組成物。

Figure 0005917517

Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
［式中、ｎは１〜４の整数である。］
Figure 0005917517
［式中、Ｒ１はＣＨ３とＣ２Ｈ４ＯＣＨ３の混合物である。］
［２］．黄色系分散染料（１）と黄色系分散染料（２）の重量比率が３：９７〜１５：８５であり、および／または、赤色系分散染料（３）と赤色系分散染料（４）の重量比率が９９：１〜８５：１５であり、および／または、青色系分散染料（５）と青色系分散染料（６）の重量比率が８５：１５〜７０：３０である上記［１］項に記載の分散染料組成物。
［３］．上記［１］または［２］項に記載の分散染料組成物を用いることを特徴とする疎水性繊維材料の染色法。
［４］．上記［３］項に記載の染色法で染色された疎水性繊維材料。
［５］．上記［４］項に記載の疎水性繊維材料を含む物品。That is, the aspects of the present invention are as follows.
[1]. A yellow disperse dye composition comprising a yellow disperse dye represented by the following formula (1) and a yellow disperse dye represented by the following formula (2):
A red disperse dye containing a red disperse dye represented by the following formula (3) and a red disperse dye represented by the following formula (4); a blue disperse dye represented by the following formula (5); The disperse dye composition containing the blue disperse dye composition containing the blue disperse dye shown by following formula (6).
Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
[Wherein, n is an integer of 1 to 4. ]
Figure 0005917517
[Wherein R 1 is a mixture of CH 3 and C 2 H 4 OCH 3 . ]
[2]. The weight ratio of the yellow disperse dye (1) to the yellow disperse dye (2) is 3:97 to 15:85 and / or the weight of the red disperse dye (3) and the red disperse dye (4). In the above item [1], the ratio is 99: 1 to 85:15, and / or the weight ratio of the blue disperse dye (5) to the blue disperse dye (6) is 85:15 to 70:30. The disperse dye composition as described.
[3]. A method for dyeing a hydrophobic fiber material, comprising using the disperse dye composition according to the item [1] or [2].
[4]. The hydrophobic fiber material dye | stained by the dyeing | staining method as described in said [3].
[5]. An article comprising the hydrophobic fiber material according to item [4].

本発明による特定の分散染料を含む三原色（黄色系、赤色系および青色系）の分散染料組成物の各々を含有する分散染料組成物、さらに、この分散染料組成物を用いて染色した合成繊維材料は、環境条件に対する優れた耐光堅牢度を持ち、かつ、三原色の耐光堅牢度のバランスも良いという特性を有し、加えて、該分散染料組成物は、染色時の良好な再現性を維持しつつ染色温度を低く抑えることが可能である。   A disperse dye composition containing each of the three primary color (yellow, red and blue) disperse dye compositions containing the specific disperse dye according to the present invention, and a synthetic fiber material dyed using the disperse dye composition Has excellent light fastness to environmental conditions and has a good balance of light fastness of the three primary colors, and in addition, the disperse dye composition maintains good reproducibility during dyeing. It is possible to keep the dyeing temperature low.

以下に、本発明を詳細に説明する。
本発明の分散染料組成物は、前記式（１）で示される黄色系分散染料および前記式（２）で示される黄色系分散染料を含む黄色系分散染料組成物、前記式（３）で示される赤色系分散染料および前記式（４）で示される赤色系分散染料を含む赤色系分散染料組成物、ならびに、前記式（５）で示される青色系分散染料および前記式（６）で示される青色系分散染料を含む青色系分散染料組成物を含有する。The present invention is described in detail below.
The disperse dye composition of the present invention is a yellow disperse dye composition comprising a yellow disperse dye represented by the formula (1) and a yellow disperse dye represented by the formula (2), and represented by the formula (3). A red disperse dye composition comprising a red disperse dye and a red disperse dye represented by formula (4), a blue disperse dye represented by formula (5) and a formula (6) A blue disperse dye composition containing a blue disperse dye is contained.

式（１）で示される黄色系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ イエロー ６４である。この分散染料は、公知文献に基づいて製造することもできるが、市販の染料を使用することもできる。
式（２）で示される黄色系分散染料については、ベンゾイミダゾール構造のフェニル基に置換するメトキシ基の置換位置は特に限定されず、混合物であってもよい。例えば、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ イエロー ７１として公知である染料が挙げられる。また、この分散染料は、公知文献に基づいて製造することもできるが、市販の染料を使用することもできる。
黄色系分散染料（１）と黄色系分散染料（２）の重量比率は、３：９７〜１５：８５が好ましい。The yellow disperse dye represented by the formula (1) is C.I. I. Disperse Yellow 64. Although this disperse dye can be manufactured based on well-known literature, a commercially available dye can also be used.
Regarding the yellow disperse dye represented by the formula (2), the substitution position of the methoxy group substituted for the phenyl group of the benzimidazole structure is not particularly limited, and may be a mixture. For example, C.I. I. A dye known as Disperse Yellow 71 can be mentioned. Moreover, although this disperse dye can also be manufactured based on well-known literature, a commercially available dye can also be used.
The weight ratio of the yellow disperse dye (1) to the yellow disperse dye (2) is preferably from 3:97 to 15:85.

式（３）で示される赤色系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ レッド ６０である。この分散染料は、公知文献に基づいて製造することもできるが、市販の染料を使用することもできる。
式（４）で示される赤色系分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ レッド ９１である。この分散染料は、公知文献に基づいて製造することもできるが、市販の染料を使用することもできる。
赤色系分散染料（３）と赤色系分散染料（４）の重量比率は、９９：１〜８５：１５が好ましい。The red disperse dye represented by the formula (3) is C.I. I. Disperse Red 60. Although this disperse dye can be manufactured based on well-known literature, a commercially available dye can also be used.
The red disperse dye represented by the formula (4) is C.I. I. Disperse Red 91. Although this disperse dye can be manufactured based on well-known literature, a commercially available dye can also be used.
The weight ratio of the red disperse dye (3) to the red disperse dye (4) is preferably 99: 1 to 85:15.

式（５）で示される青色系分散染料については、臭素原子の置換数、置換位置は置換可能であれば特に限定されず、それらの混合物であってもよい。例えば、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ ブルー ５６として公知である染料が挙げられる。また、この分散染料は、公知文献に基づいて製造することもできるが、市販の染料を使用することもできる。
式（６）で示される青色系分散染料は、Ｒ１について混合物であり、例えば、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ ブルー ２０４が挙げられる。この分散染料は、公知文献に基づいて製造することもできるが、市販の染料を使用することもできる。
青色系分散染料（５）と青色系分散染料（６）の重量比率は、８５：１５〜７０：３０が好ましい。The blue disperse dye represented by the formula (5) is not particularly limited as long as the number and position of substitution of bromine atoms can be substituted, and may be a mixture thereof. For example, C.I. I. A dye known as Disperse Blue 56 may be mentioned. Moreover, although this disperse dye can also be manufactured based on well-known literature, a commercially available dye can also be used.
The blue disperse dye represented by the formula (6) is a mixture of R 1 , for example, C.I. I. Disperse Blue 204. Although this disperse dye can be manufactured based on well-known literature, a commercially available dye can also be used.
The weight ratio of the blue disperse dye (5) and the blue disperse dye (6) is preferably 85:15 to 70:30.

本発明の分散染料組成物において、黄色系分散染料組成物、赤色系分散染料組成物及び青色系分散染料組成物の各々の重量割合は、所望の染色の色合い次第であり、（０重量％超１００重量％未満である限りは）特に限定されるものではないが、例えば、通常０重量％超９９．９９重量％以下、典型的には０重量％超９９．９重量％以下、より典型的には０重量％超９９重量％以下、さらに典型的には０重量％超９８重量％以下であってよい。   In the disperse dye composition of the present invention, the weight ratio of each of the yellow disperse dye composition, the red disperse dye composition, and the blue disperse dye composition depends on the desired dyeing shade, and exceeds 0% by weight. For example, it is usually more than 0% by weight and less than 99.99% by weight, typically more than 0% by weight and less than 99.9% by weight, as long as it is less than 100% by weight. May be more than 0% by weight and 99% by weight or less, more typically more than 0% by weight and 98% by weight or less.

本発明の分散染料組成物には、色合いを調整するため、若しくは、耐光堅牢度、染色特性等を調整するために、さらに他の分散染料を混合して使用することができる。他の分散染料は、染色時に加えて使用してもよい。
同様にして分散染料以外の染料、例えば、直接染料、反応性染料、塩基性染料等を混合して使用することもできる。他の染料や染色薬剤は、染色時に加えて使用してもよい。
その他、本発明の分散染料組成物は、水等の溶剤、後記のキャリヤーや後記の分散剤を含んでいてもよい。In the disperse dye composition of the present invention, other disperse dyes can be further mixed and used in order to adjust the hue, or to adjust the light fastness, dyeing characteristics, and the like. Other disperse dyes may be used in addition to the dyeing.
Similarly, dyes other than disperse dyes, for example, direct dyes, reactive dyes, basic dyes and the like can be mixed and used. Other dyes and dyeing agents may be used in addition to the dyeing.
In addition, the disperse dye composition of the present invention may contain a solvent such as water, a carrier described later, and a dispersant described later.

本発明の分散染料組成物は、分散染料の各原末を必要量混合した後、微粒子化（分散化）処理を施して所望の分散染料組成物としてもよい。または、これらの各染料原末について別々に微粒子化（分散化）処理を施した後、混合してもよい。後者にあっては、染浴中で個々に微粒子化（分散化）処理を施された分散染料を添加して染浴中にて形成させてもよい。微粒子化（分散化）処理には、通常、後記のように分散剤を使用する。また、微粒子化された分散染料組成物に、後記の分散剤を後から加えてもよい。   The disperse dye composition of the present invention may be formed into a desired disperse dye composition by mixing a necessary amount of each raw material of a disperse dye and then subjecting it to a fine particle (dispersion) treatment. Or you may mix, after performing the micronization (dispersion) process separately about each of these dye raw materials. In the latter case, it may be formed in the dye bath by adding a disperse dye which has been individually finely divided (dispersed) in the dye bath. In the fine particle (dispersion) treatment, a dispersant is usually used as described later. Moreover, you may add the below-mentioned dispersing agent later to the disperse dye composition finely divided.

一般的に微粒子化処理としては、ナフタレンスルホン酸とアルキルベンゼンスルホン酸とのホルマリン縮合物、ナフタレンスルホン酸のホルマリン縮合物、クレゾールスルホン酸のホルマリン縮合物、クレゾールと２−ナフトール−６−スルホン酸とのホルマリン縮合物、アルキルナフタレンスルホン酸のホルマリン縮合物、クレオソート油スルホン酸のホルマリン縮合物等の分散剤；リグニンスルホン酸等のアニオン性分散剤；エチレンオキサイドとプロピレンオキサイドとのブロック共重合物、アルキルフェノールのエチレンオキサイド付加物、ポリスチレン化フェノールのエチレンオキサイド付加物等の非イオン性分散剤；前記のアニオン性分散剤と前記の非イオン性分散剤との混合物等と、分散染料原末とを、少量の水の存在下で、ボールミルあるいはサンドミル等の粉砕機を用いて、通常０．２〜２μ程度になるまで十分に湿式粉砕する方法が挙げられる。   In general, the fine particle treatment includes formalin condensate of naphthalene sulfonic acid and alkylbenzene sulfonic acid, formalin condensate of naphthalene sulfonic acid, formalin condensate of cresol sulfonic acid, cresol and 2-naphthol-6-sulfonic acid. Dispersants such as formalin condensate, formalin condensate of alkylnaphthalene sulfonic acid, formalin condensate of creosote oil sulfonic acid; anionic dispersant such as lignin sulfonic acid; block copolymer of ethylene oxide and propylene oxide, alkylphenol A small amount of a nonionic dispersant such as an ethylene oxide adduct of polystyrene and an ethylene oxide adduct of polystyreneated phenol; a mixture of the anionic dispersant and the nonionic dispersant, and a disperse dye bulk powder In the presence of water Ball mill or using a pulverizer such as a sand mill, and a method to sufficiently wet ground to usually about 0.2～2Myu.

本発明の分散染料組成物は、例えば、微粒子化されたままの液状乃至ペースト状で、あるいは、スプレ−乾燥法等により乾燥してから染色に供される。   The disperse dye composition of the present invention is used, for example, in the form of liquid or paste as it is finely divided, or after drying by a spray drying method or the like.

次に、本発明の分散染料組成物を用いる疎水性繊維材料の染色法について説明する。該疎水性繊維材料としては、特に限定されないが、合成繊維材料であるポリエステル（ＰＥＴ）繊維、カチオン可染ポリエステル（ＣＤＰ）繊維、トリアセテート繊維、ジアセテート繊維、ポリアミド繊維またはこれら同士の混紡品が挙げられる。さらに、これらとレーヨン等の再生繊維あるいは木綿、絹、羊毛等の天然繊維との混紡品であってもよい。また、前記疎水性繊維材料の太さとしては、特に限定されないが、平均の太さが０．１〜１０ｄ（デニ−ル）程度が好ましい。   Next, a method for dyeing a hydrophobic fiber material using the disperse dye composition of the present invention will be described. Although it does not specifically limit as this hydrophobic fiber material, The polyester (PET) fiber which is a synthetic fiber material, a cationic dyeable polyester (CDP) fiber, a triacetate fiber, a diacetate fiber, a polyamide fiber, or a blended product of these is mentioned. It is done. Further, it may be a blend of these and recycled fibers such as rayon or natural fibers such as cotton, silk, wool. The thickness of the hydrophobic fiber material is not particularly limited, but the average thickness is preferably about 0.1 to 10 d (denier).

該染色法としては、本発明の分散染料組成物を溶解した水性媒体中に該繊維材料を浸漬し、加圧下、好ましくは１０５℃以上、更に好ましくは１１０℃〜１４０℃で、好ましくは３０分〜１時間染色することができる。特に好ましくは１２０℃〜１３０℃で３０分〜４５分染色することができる。また、ｏ−フェニルフェノールやトリクロロベンゼン等のキャリヤーの存在下、例えば、水の沸騰状態で染色することもできる。あるいは、本発明の分散染料組成物の染料分散液を布にパディングし、１５０〜２３０℃で３０秒〜１分間の乾熱処理を施す、所謂サーモゾル方式での染色も可能である。   As the dyeing method, the fiber material is immersed in an aqueous medium in which the disperse dye composition of the present invention is dissolved, and is preferably 105 ° C or higher, more preferably 110 ° C to 140 ° C, and preferably 30 minutes under pressure. Can be stained for ~ 1 hour. Particularly preferably, the dyeing can be performed at 120 to 130 ° C. for 30 to 45 minutes. It can also be dyed, for example, in the boiling state of water in the presence of a carrier such as o-phenylphenol or trichlorobenzene. Alternatively, dyeing by a so-called thermosol method in which a dye dispersion of the disperse dye composition of the present invention is padded on a cloth and subjected to a dry heat treatment at 150 to 230 ° C. for 30 seconds to 1 minute is also possible.

一方、本発明の分散染料組成物を用いて、天然糊剤（例えば、ローカストビーンガム、グアーガム等）、加工糊剤（例えば、カルボキシメチルセルロース等の繊維素誘導体、加工ローカストビーンガム等）、合成糊剤（例えば、ポリビニルアルコール、ポリビニル酢酸等）等とともに捺染糊を調製し、布に印捺した後にスチーミングまたはサーモゾル処理を施す捺染法による染色を行なってもよい。   On the other hand, using the disperse dye composition of the present invention, natural paste (for example, locust bean gum, guar gum, etc.), processed paste (for example, fiber derivatives such as carboxymethyl cellulose, processed locust bean gum, etc.), synthetic paste A printing paste may be prepared together with an agent (for example, polyvinyl alcohol, polyvinyl acetic acid, etc.), printed on a cloth, and then dyed by a printing method in which a steaming or thermosol treatment is performed.

また、本発明の分散染料組成物にグリセリンあるいはジエチレングリコール等の不乾性剤を添加して得たインクを調製し、パディング等によって予め糊剤等が付与された布に、インクジェット方式のプリンターを用いてプリントした後、スチーミングまたはサーモゾル処理するインクジェット捺染法による染色を行ってもよい。   In addition, an ink obtained by adding a non-drying agent such as glycerin or diethylene glycol to the disperse dye composition of the present invention is prepared, and an ink jet printer is used on a cloth to which a paste or the like is applied in advance by padding or the like. After printing, dyeing may be performed by an inkjet printing method in which steaming or thermosol processing is performed.

染色する際に本発明の分散染料組成物の使用量は任意であるが、例えば、３デニ−ルの繊維材料を使用する場合には０．０５〜２０％ｏ．ｗ．ｆ．（対繊維重量）程度が好ましく、０．２〜１０％ｏ．ｗ．ｆ．程度が特に好ましい。   The amount of the disperse dye composition of the present invention used in dyeing is arbitrary. For example, when a 3 denier fiber material is used, 0.05 to 20% o.d. w. f. (Weight to fiber) degree is preferable, 0.2 to 10% o. w. f. The degree is particularly preferred.

以下の実施例により本発明を詳細に説明するが、本発明はこれらの例に限定されるものではない。実施例において、部は重量部を、％は重量％をそれぞれ意味する。   The present invention will be described in detail by the following examples, but the present invention is not limited to these examples. In Examples, “part” means “part by weight” and “%” means “% by weight”.

［参考例１］
前記式（１）で示される黄色系分散染料（Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ イエロー ６４を使用；以下「分散染料（１）」と称する。）の原末７．８部、前記式（２）で示される黄色系分散染料（Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ イエロー ７１を使用；以下「分散染料（２）」と称する。）の原末９２．２部を合わせ、これらの原末の合計量と同量の分散剤（デモールＮ：β−ナフタレンスルホン酸ホルマリン縮合物のナトリウム塩）を加えて微粒子化処理を行って、黄色系分散染料組成物（Ａ−１）を製造した。[Reference Example 1]
7.8 parts of bulk powder of the yellow disperse dye represented by the formula (1) (using CI Disperse Yellow 64; hereinafter referred to as “dispersion dye (1)”), represented by the formula (2) 92.2 parts of the powdery yellow disperse dye (using CI Disperse Yellow 71; hereinafter referred to as “dispersion dye (2)”) is combined, and the same amount of dispersion as the total amount of these powders An agent (Demol N: sodium salt of β-naphthalenesulfonic acid formalin condensate) was added to carry out micronization treatment to produce a yellow disperse dye composition (A-1).

［参考例２］
前記式（３）で示される赤色系分散染料（Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ レッド ６０を使用；以下「分散染料（３）」と称する。）の原末９０部、前記式（４）で示される赤色系分散染料（Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ レッド ９１を使用；以下「分散染料（４）」と称する。）の原末１０部を合わせ、これらの原末の合計量と同量の分散剤（デモールＮ：β−ナフタレンスルホン酸ホルマリン縮合物のナトリウム塩）を加えて微粒子化処理を行って、赤色系分散染料組成物（Ｂ−１）を製造した。[Reference Example 2]
90 parts of the raw powder of the red disperse dye represented by the formula (3) (using CI Disperse Red 60; hereinafter referred to as “dispersion dye (3)”), the red color represented by the formula (4) 10 parts of the raw powder of the system disperse dye (using CI Disperse Red 91; hereinafter referred to as “dispersion dye (4)”) is combined, and the same amount of dispersant (Demol N) : Sodium salt of β-naphthalene sulfonic acid formalin condensate) was added to form a fine particle to produce a red disperse dye composition (B-1).

［参考例３］
前記式（５）で示される青色系分散染料（Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ ブルー ５６を使用；以下「分散染料（５）」と称する。）の原末７５部、前記式（６）で示される青色系分散染料（Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ ブルー ２０４を使用；以下「分散染料（６）」と称する。）の原末２５部を合わせ、これらの原末の合計量と同量の分散剤（デモールＮ：β−ナフタレンスルホン酸ホルマリン縮合物のナトリウム塩）を加えて微粒子化処理を行って、青色系分散染料組成物（Ｃ−１）を製造した。[Reference Example 3]
75 parts of the bulk powder of the blue disperse dye represented by the formula (5) (using CI Disperse Blue 56; hereinafter referred to as “dispersion dye (5)”), the blue discoloration represented by the formula (6) 25 parts by weight of a base disperse dye (using CI Disperse Blue 204; hereinafter referred to as “dispersion dye (6)”) is combined with a dispersant (Demol N) in the same amount as the total amount of these base powders. : Sodium salt of β-naphthalenesulfonic acid formalin condensate) was added to carry out micronization treatment to produce a blue disperse dye composition (C-1).

［参考例４］
参考例１と同様に、分散染料（１）の原末１０部、分散染料（２）の原末９０部を用いて黄色系分散染料組成物（Ａ−２）を製造した。[Reference Example 4]
In the same manner as in Reference Example 1, a yellow disperse dye composition (A-2) was produced using 10 parts of the bulk powder of the disperse dye (1) and 90 parts of the bulk powder of the disperse dye (2).

［参考例５］
参考例２と同様に、分散染料（３）の原末９５部、分散染料（４）の原末５部を用いて赤色系分散染料組成物（Ｂ−２）を製造した。[Reference Example 5]
Similarly to Reference Example 2, a red disperse dye composition (B-2) was produced using 95 parts of the bulk powder of the disperse dye (3) and 5 parts of the bulk powder of the disperse dye (4).

［参考例６］
参考例３と同様に、分散染料（５）の原末７０部、分散染料（６）の原末３０部を用いて青色系分散染料組成物（Ｃ−２）を製造した。[Reference Example 6]
In the same manner as in Reference Example 3, a blue disperse dye composition (C-2) was produced using 70 parts of the bulk powder of the disperse dye (5) and 30 parts of the bulk powder of the disperse dye (6).

［参考例７］
参考例１と同様に、分散染料（１）の原末５部、分散染料（２）の原末９５部を用いて黄色系分散染料組成物（Ａ−３）を製造した。[Reference Example 7]
In the same manner as in Reference Example 1, a yellow disperse dye composition (A-3) was produced using 5 parts of the bulk powder of the disperse dye (1) and 95 parts of the bulk powder of the disperse dye (2).

［参考例８］
参考例２と同様に、分散染料（３）の原末９７部、分散染料（４）の原末３部を用いて赤色系分散染料組成物（Ｂ−３）を製造した。[Reference Example 8]
In the same manner as in Reference Example 2, a red disperse dye composition (B-3) was produced using 97 parts of the bulk powder of the disperse dye (3) and 3 parts of the bulk powder of the disperse dye (4).

［参考例９］
参考例３と同様に、分散染料（５）の原末８０部、分散染料（６）の原末２０部を用いて青色系分散染料組成物（Ｃ−３）を製造した。[Reference Example 9]
In the same manner as in Reference Example 3, a blue disperse dye composition (C-3) was produced using 80 parts of the bulk powder of the disperse dye (5) and 20 parts of the bulk powder of the disperse dye (6).

［実施例１］
参考例１の黄色系分散染料組成物（Ａ−１）０．１３１％ｏ．ｗ．ｆ．（対繊維重量）と、参考例２の赤色系分散染料組成物（Ｂ−１）０．０５０％ｏ．ｗ．ｆ．（対繊維重量）と、参考例３の青色系分散染料組成物（Ｃ−１）を０．０６１％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、各染色物に対して８０℃、１０分間の還元洗浄を施した後に、水洗、乾燥して染色物（ポリエステル染色布）を得た。[Example 1]
Yellow disperse dye composition (A-1) of Reference Example 1 0.131% o.d. w. f. (Weight to fiber) and the red disperse dye composition of Reference Example 2 (B-1) 0.050% o. w. f. (Weight to fiber) and the blue disperse dye composition (C-1) of Reference Example 3 at 0.061% o. w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. And a dye bath with a total amount of 2000 parts is prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is immersed, and 120 ° C., 125 ° C., 130 ° C. and 135 ° C. Staining for 40 minutes at each temperature. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. Each dyed product was subjected to reduction washing at 80 ° C. for 10 minutes, then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［実施例２］
参考例４の黄色系分散染料組成物（Ａ−２）０．１３１％ｏ．ｗ．ｆ．（対繊維重量）と、参考例５の赤色系分散染料組成物（Ｂ−２）０．０５０％ｏ．ｗ．ｆ．（対繊維重量）と、参考例６の青色系分散染料組成物（Ｃ−２）０．０６１％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１３５℃で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、染色物に対して８０℃、１０分間の還元洗浄を施した後に、水洗、乾燥して染色物（ポリエステル染色布）を得た。[Example 2]
Yellow disperse dye composition (A-2) of Reference Example 4 0.131% o.d. w. f. (Weight to fiber) and red disperse dye composition (B-2) of Reference Example 5 0.050% o. w. f. (Weight to fiber) and 0.061% o. Blue disperse dye composition (C-2) of Reference Example 6 w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. Was added, and a dye bath having a total amount of 2000 parts was prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) was immersed and dyed at 135 ° C. for 40 minutes. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. The dyed product was subjected to reduction cleaning at 80 ° C. for 10 minutes, then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［実施例３］
参考例７の黄色系分散染料組成物（Ａ−３）０．１３１％ｏ．ｗ．ｆ．（対繊維重量）と、参考例８の赤色系分散染料組成物（Ｂ−３）０．０５０％ｏ．ｗ．ｆ．（対繊維重量）と、参考例９の青色系分散染料組成物（Ｃ−３）０．０６１％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１３５℃で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、染色物に対して８０℃、１０分間の還元洗浄を施した後に、水洗、乾燥して染色物（ポリエステル染色布）を得た。[Example 3]
Yellow disperse dye composition (A-3) of Reference Example 7 0.131% o.d. w. f. (Weight to fiber) and the red disperse dye composition of Reference Example 8 (B-3) 0.050% o. w. f. (Weight to fiber) and 0.061% o.e. blue disperse dye composition (C-3) of Reference Example 9 w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. Was added, and a dye bath having a total amount of 2000 parts was prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) was immersed and dyed at 135 ° C. for 40 minutes. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. The dyed product was subjected to reduction cleaning at 80 ° C. for 10 minutes, then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［比較例１］
市販のダイスター社のＤｉａｎｉｘ Ｙｅｌｌｏｗ ＨＬＡを０．０９４％ｏ．ｗ．ｆ．（対繊維重量）と、Ｄｉａｎｉｘ Ｒｅｄ ＨＬＡを０．０３２％ｏ．ｗ．ｆ．（対繊維重量）と、Ｄｉａｎｉｘ Ｂｌｕｅ ＨＬＡを０．０７９％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、各染色物に対して８０℃、１０分間の還元洗浄を施した後に、水洗、乾燥して染色物（ポリエステル染色布）を得た。[Comparative Example 1]
Commercially available Distar Yellow HLA from Dystar is 0.094% o. w. f. (Vs. fiber weight) and Dianix Red HLA 0.032% o.d. w. f. (Vs. fiber weight) and Dianix Blue HLA 0.079% o. w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. And a dye bath with a total amount of 2000 parts is prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is immersed, and 120 ° C., 125 ° C., 130 ° C. and 135 ° C. Staining for 40 minutes at each temperature. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. Each dyed product was subjected to reduction washing at 80 ° C. for 10 minutes, then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［試験例１］
［耐光堅牢度試験］
フェードメーター（ブラックパネル温度：８９℃±３℃、８４メガジュール）キセノンランプを用いて、１６２Ｗ／平方メートル、１４４時間条件で、染色物に光照射し、照射部分の変褪色をＪＩＳ Ｌ−０８０４の変褪色用グレースケールにて判定した。
実施例１の１３５℃で染色したポリエステル染色布、実施例２、実施例３で染色したポリエステル染色布の耐光堅牢度は、すべて４−５級であった。
比較例１の１３５℃で染色したポリエステル染色布の耐光堅牢度は３−４級であった。[Test Example 1]
[Light fastness test]
Using a fade meter (black panel temperature: 89 ° C. ± 3 ° C., 84 megajoule) xenon lamp, the dyed product was irradiated with light under the condition of 162 W / square meter for 144 hours. Judgment was made with a gray scale for color change.
The fastness to light of the polyester dyed cloth dyed at 135 ° C. in Example 1 and the polyester dyed cloth dyed in Example 2 and Example 3 were all grades 4-5.
The light fastness of the polyester dyed fabric dyed at 135 ° C. in Comparative Example 1 was grade 3-4.

また、実施例１の１３５℃で染色したポリエステル染色布、実施例２、実施例３で染色したポリエステル染色布の表裏の色を比較してみたところ、すべて表裏の色の差が小さかった（一見して明らかな相違は目視されなかった）。それとは対照的に、比較例１の１３５℃で染色したポリエステル染色布の表裏の色の差は大きかった（相違が一見して明らかであった）。   Further, when comparing the front and back colors of the polyester dyed fabric dyed at 135 ° C. of Example 1 and the polyester dyed fabric dyed in Example 2 and Example 3, the difference in color between the front and back surfaces was all small (looks) And no obvious difference was observed). In contrast, the difference in color between the front and back sides of the polyester dyed fabric dyed at 135 ° C. in Comparative Example 1 was large (the difference was apparent at first glance).

［実施例４］
参考例１の黄色系分散染料組成物（Ａ−１）０．２６２％ｏ．ｗ．ｆ．（対繊維重量）と、参考例２の赤色系分散染料組成物（Ｂ−１）０．１００％ｏ．ｗ．ｆ．（対繊維重量）と、参考例３の青色系分散染料組成物（Ｃ−１）０．１２２％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、各染色物を８０℃、１０分間の還元洗浄を施した後に、水洗、乾燥して染色物（ポリエステル染色布）を得た。[Example 4]
Yellow disperse dye composition (A-1) of Reference Example 1 0.262% o.d. w. f. (Weight to fiber) and 0.100% o.d. red disperse dye composition (B-1) of Reference Example 2. w. f. (Weight to fiber) and 0.12% o. Blue disperse dye composition (C-1) of Reference Example 3 w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. And a dye bath with a total amount of 2000 parts is prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is immersed, and 120 ° C., 125 ° C., 130 ° C. and 135 ° C. Staining for 40 minutes at each temperature. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. Each dyed product was subjected to reduction washing at 80 ° C. for 10 minutes, and then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［実施例５］
参考例１の黄色系分散染料組成物（Ａ−１）０．５２４％ｏ．ｗ．ｆ．（対繊維重量）と、参考例２の赤色系分散染料組成物（Ｂ−１）０．２００％ｏ．ｗ．ｆ．（対繊維重量）と、参考例３の青色系分散染料組成物（Ｃ−１）０．２４４％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、各染色物を８０℃、１０分間の還元洗浄を施した後に、水洗、乾燥して染色物（ポリエステル染色布）を得た。[Example 5]
Yellow disperse dye composition (A-1) of Reference Example 1 0.524% o.d. w. f. (Weight to fiber) and the red disperse dye composition of Reference Example 2 (B-1) 0.200% o. w. f. (Weight to fiber) and blue disperse dye composition (C-1) of Reference Example 3 0.244% o.d. w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. And a dye bath with a total amount of 2000 parts is prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is immersed, and 120 ° C., 125 ° C., 130 ° C. and 135 ° C. Staining for 40 minutes at each temperature. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. Each dyed product was subjected to reduction washing at 80 ° C. for 10 minutes, and then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［比較例２］
市販のダイスター社のＤｉａｎｉｘ Ｙｅｌｌｏｗ ＨＬＡを０．１８７％ｏ．ｗ．ｆ．（対繊維重量）と、Ｄｉａｎｉｘ Ｒｅｄ ＨＬＡを０．０６４％ｏ．ｗ．ｆ．（対繊維重量）と、Ｄｉａｎｉｘ Ｂｌｕｅ ＨＬＡを０．１５８％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、各染色物を８０℃、１０分間の還元洗浄を施した後に水洗、乾燥して染色物（ポリエステル染色布）を得た。[Comparative Example 2]
A commercially available Dystar Dianix Yellow HLA is 0.187% o.d. w. f. (Vs. fiber weight) and Dianix Red HLA 0.064% o.d. w. f. (Vs. fiber weight) and Dianix Blue HLA 0.158% o.d. w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. And a dye bath with a total amount of 2000 parts is prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is immersed, and 120 ° C., 125 ° C., 130 ° C. and 135 ° C. Staining for 40 minutes at each temperature. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. Each dyed product was subjected to reduction cleaning at 80 ° C. for 10 minutes, then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［比較例３］
市販のダイスター社のＤｉａｎｉｘ Ｙｅｌｌｏｗ ＨＬＡを０．３７４％ｏ．ｗ．ｆ．（対繊維重量）と、Ｄｉａｎｉｘ Ｒｅｄ ＨＬＡを０．１２８％ｏ．ｗ．ｆ．（対繊維重量）と、Ｄｉａｎｉｘ Ｂｌｕｅ ＨＬＡを０．３１６％ｏ．ｗ．ｆ．（対繊維重量）とを水に加え、酢酸と酢酸ナトリウムによりｐＨ４．５に調整し、サンライフ ＬＰ−２４０（日華化学（株）製、紫外線吸収剤）２．０％ｏ．ｗ．ｆ．を加え、全量を２０００部とした染浴を調製し、ポリエステル繊維起毛織物（表側が０．３デニールと裏側が３デニール糸使用）１００部を浸漬し、１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度で４０分間染色した。次いで、４５％のカセイソーダ６部、ハイドロサルファイト６部、サンモールＲＣー７００（日華化学（株）製、アニオン性界面活性剤）３部に水を加えて全量３０００部とした浴で、各染色物を８０℃、１０分間の還元洗浄を施した後に水洗、乾燥して染色物（ポリエステル染色布）を得た。[Comparative Example 3]
Commercially available Daistar Yellow HLA manufactured by Daistar Co., Ltd. was 0.374% o.d. w. f. (Vs. fiber weight) and Dianix Red HLA 0.128% o.d. w. f. (Vs. fiber weight) and Dianix Blue HLA 0.316% o.d. w. f. (Weight to fiber) was added to water, adjusted to pH 4.5 with acetic acid and sodium acetate, and Sunlife LP-240 (manufactured by Nikka Chemical Co., Ltd., UV absorber) 2.0% o.d. w. f. And a dye bath with a total amount of 2000 parts is prepared, and 100 parts of a polyester fiber raised fabric (using 0.3 denier on the front side and 3 denier on the back side) is immersed, and 120 ° C., 125 ° C., 130 ° C. and 135 ° C. Staining for 40 minutes at each temperature. Next, 6 parts of 45% caustic soda, 6 parts of hydrosulfite, 3 parts of Sunmall RC-700 (manufactured by Nikka Chemical Co., Ltd., anionic surfactant) are added to water to make a total of 3000 parts. Each dyed product was subjected to reduction cleaning at 80 ° C. for 10 minutes, then washed with water and dried to obtain a dyed product (polyester dyed cloth).

［試験例２］
実施例１、実施例４、実施例５、比較例１、比較例２、比較例３で染色した各ポリエステル染色布について、分光測色器（Ｍａｃｂｅｔｈ社製Ｃｏｌｏｒ−Ｅｙｅ ３１００）にて色相を測定した。１３５℃の染色布の色相を標準として、１２０℃、１２５℃、１３０℃の各々の染色布の色相の差ΔＥを表１に示す。色相の差ΔＥは、小さいほど優れている。すなわち、１３５℃の染色布の色相（標準）に対するより低い温度の色相の差ΔＥが小さいほど、低下された温度での染色時の良好な再現性が実証される。[Test Example 2]
About each polyester dyed cloth dyed in Example 1, Example 4, Example 5, Comparative Example 1, Comparative Example 2, and Comparative Example 3, the hue was measured with a spectrocolorimeter (Color-Eye 3100 manufactured by Macbeth). did. Table 1 shows the hue difference ΔE between the dyed fabrics at 120 ° C, 125 ° C, and 130 ° C with the hue of the dyed fabric at 135 ° C as a standard. The smaller the hue difference ΔE, the better. That is, the smaller the hue difference ΔE at a lower temperature relative to the hue (standard) of the dyed fabric at 135 ° C., the better the reproducibility when dyeing at a reduced temperature.

［表１］各温度条件の染色布の色相の差ΔＥ

Figure 0005917517
[Table 1] Hue difference ΔE of dyed fabric under each temperature condition
Figure 0005917517

実施例１、実施例４、実施例５に較べて比較例１、比較例２、比較例３の染色布は、染色温度が下がると色相差が大きくなってしまい、１２５℃以下では実用に耐えないものであった。逆に言えば、比較例１、比較例２、比較例３に較べて実施例１、実施例４、実施例５の染色布は、染色温度が下がっても色相差が格段に小さかった。   Compared with Example 1, Example 4, and Example 5, the dyed fabrics of Comparative Example 1, Comparative Example 2, and Comparative Example 3 have a large hue difference when the dyeing temperature is lowered, and are practically used at 125 ° C. or lower. It was not. In other words, compared with Comparative Example 1, Comparative Example 2, and Comparative Example 3, the dyed fabrics of Example 1, Example 4, and Example 5 had much smaller hue differences even when the dyeing temperature was lowered.

［実施例６］
実施例２において、染色温度を１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度とし、染色時間を１０分、３０分及び６０分の各々の時間とした以外は同じ条件で染色を行い、各々の染色物（ポリエステル染色布）を得た。[Example 6]
In Example 2, dyeing is performed under the same conditions except that the dyeing temperature is 120 ° C, 125 ° C, 130 ° C, and 135 ° C, and the dyeing time is 10 minutes, 30 minutes, and 60 minutes. Each dyed product (polyester dyed cloth) was obtained.

［比較例４］
比較例２において、染色温度を１２０℃、１２５℃、１３０℃及び１３５℃の各々の温度とし、染色時間を１０分、３０分及び６０分の各々の時間とした以外は同じ条件で染色を行い、各々の染色物（ポリエステル染色布）を得た。[Comparative Example 4]
In Comparative Example 2, dyeing is performed under the same conditions except that the dyeing temperature is 120 ° C, 125 ° C, 130 ° C, and 135 ° C, and the dyeing time is 10 minutes, 30 minutes, and 60 minutes. Each dyed product (polyester dyed cloth) was obtained.

［試験例３］
実施例６、比較例４で染色した各ポリエステル染色布について、分光測色器（Ｍａｃｂｅｔｈ社製Ｃｏｌｏｒ−Ｅｙｅ ３１００）にて色相を測定した。各例の１３５℃、６０分の染色布の色相を標準として、１２０℃、１２５℃及び１３０℃、並びに、１０分、３０分及び６０分の各々の染色布の色相の差ΔＥを表２に示す。上記同様、低下された温度での染色時の良好な再現性の観点から、色相の差ΔＥは小さいほど優れている。[Test Example 3]
About each polyester dyeing cloth dye | stained by Example 6 and the comparative example 4, the hue was measured with the spectrocolorimeter (Color-Eye 3100 by Macbeth). Table 2 shows the difference ΔE between the hues of the dyed fabrics at 120 ° C, 125 ° C and 130 ° C, and 10 minutes, 30 minutes and 60 minutes, with the hues of the dyed fabrics at 135 ° C and 60 minutes of each example as standard. Show. As described above, from the viewpoint of good reproducibility during dyeing at a reduced temperature, the smaller the hue difference ΔE, the better.

［表２］各温度及び各時間条件の染色布の色相の差ΔＥ

Figure 0005917517
[Table 2] Color difference ΔE of dyed fabric at each temperature and each time condition
Figure 0005917517

実施例６の分散染料組成物は、比較例４の分散染料組成物に較べて染色温度が低くなっても、また、染色時間が短くなっても色相差が小さかった。   The disperse dye composition of Example 6 had a smaller hue difference even when the dyeing temperature was lower and the dyeing time was shorter than the disperse dye composition of Comparative Example 4.

以上の結果から明らかなように、本発明の分散染料組成物は、市販の分散染料組成物と比べ疎水性繊維材料を染色した際に優れた耐光堅牢度を示した。さらに、本発明の分散染料組成物は、太さの異なる疎水性繊維材料を表裏とする繊維材料を染色しても，表裏ほぼ同様に染色され、染色時の染色特性が揃っていた。加えて、染色温度が低くても染色時間が短くても、色相の差の少ない染色物が得られ、省エネルギーの観点からも本発明の分散染料組成物は優れていた。一方、比較例の市販の分散染料の混合組成物は、太さの違う繊維材料の染色特性が揃わず、染色温度や染色時間の影響を受けて色相の差を生じ、染色温度の低減や染色時間の短縮はできないことが分かった。
これらの結果は、本発明の分散染料組成物の実用性の高さを示している。As is apparent from the above results, the disperse dye composition of the present invention exhibited excellent light fastness when dyeing a hydrophobic fiber material as compared with a commercially available disperse dye composition. Furthermore, even if the disperse dye composition of the present invention dyes a fiber material having front and back hydrophobic fiber materials having different thicknesses, the disperse dye composition is dyed in substantially the same manner, and the dyeing characteristics at the time of dyeing are uniform. In addition, even if the dyeing temperature is low or the dyeing time is short, a dyed product having a small difference in hue is obtained, and the disperse dye composition of the present invention is excellent from the viewpoint of energy saving. On the other hand, the mixed composition of commercially available disperse dyes in the comparative example does not have the same dyeing characteristics of fiber materials with different thicknesses, and causes a difference in hue due to the influence of dyeing temperature and dyeing time, thereby reducing dyeing temperature and dyeing. It turns out that the time cannot be shortened.
These results show the high practicality of the disperse dye composition of the present invention.

本発明による分散染料組成物は、環境条件に対する優れた耐光堅牢度を持ち、かつ、三原色の耐光堅牢度のバランスも良いという特性を有し、加えて、染色時の良好な再現性を維持しつつ染色温度を低く抑えることが可能である。従って、この分散染料組成物は、高温高湿条件に曝されることが多い自動車内装材料用の合成繊維材料の染色のために好適に用いることができる。   The disperse dye composition according to the present invention has excellent light fastness against environmental conditions and has a good balance of light fastness of the three primary colors, and in addition, maintains good reproducibility during dyeing. It is possible to keep the dyeing temperature low. Therefore, this disperse dye composition can be suitably used for dyeing synthetic fiber materials for automobile interior materials that are often exposed to high temperature and high humidity conditions.

Claims (5)

下記式（１）で示される黄色系分散染料、および下記式（２）で示される黄色系分散染料を含む黄色系分散染料組成物、
下記式（３）で示される赤色系分散染料、および下記式（４）で示される赤色系分散染料を含む赤色系分散染料組成物、ならびに
下記式（５）で示される青色系分散染料、および下記式（６）で示される青色系分散染料を含む青色系分散染料組成物
を含有する分散染料組成物。
Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
［式中、ｎは１〜４の整数である。］
Figure 0005917517
［式中、Ｒ１はＣＨ３とＣ２Ｈ４ＯＣＨ３の混合物である。］A yellow disperse dye composition comprising a yellow disperse dye represented by the following formula (1) and a yellow disperse dye represented by the following formula (2):
A red disperse dye containing a red disperse dye represented by the following formula (3) and a red disperse dye represented by the following formula (4); a blue disperse dye represented by the following formula (5); The disperse dye composition containing the blue disperse dye composition containing the blue disperse dye shown by following formula (6).
Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
Figure 0005917517
[Wherein, n is an integer of 1 to 4. ]
Figure 0005917517
[Wherein R 1 is a mixture of CH 3 and C 2 H 4 OCH 3 . ] 黄色系分散染料（１）と黄色系分散染料（２）の重量比率が３：９７〜１５：８５であり、および／または、赤色系分散染料（３）と赤色系分散染料（４）の重量比率が９９：１〜８５：１５であり、および／または、青色系分散染料（５）と青色系分散染料（６）の重量比率が８５：１５〜７０：３０である請求項１に記載の分散染料組成物。   The weight ratio of the yellow disperse dye (1) to the yellow disperse dye (2) is 3:97 to 15:85 and / or the weight of the red disperse dye (3) and the red disperse dye (4). 2. The ratio according to claim 1, wherein the ratio is 99: 1 to 85:15 and / or the weight ratio of the blue disperse dye (5) to the blue disperse dye (6) is 85:15 to 70:30. Disperse dye composition. 請求項１または２に記載の分散染料組成物を用いることを特徴とする疎水性繊維材料の染色法。   A method for dyeing a hydrophobic fiber material, wherein the disperse dye composition according to claim 1 or 2 is used. 請求項３に記載の染色法で染色された疎水性繊維材料。   A hydrophobic fiber material dyed by the dyeing method according to claim 3. 請求項４に記載の疎水性繊維材料を含む物品。   An article comprising the hydrophobic fiber material according to claim 4.
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