JPH06166828A - Highly light-resistant coloring composition and method for coloring hydrophobic material using the same - Google Patents

Highly light-resistant coloring composition and method for coloring hydrophobic material using the same

Info

Publication number
JPH06166828A
JPH06166828A JP4323033A JP32303392A JPH06166828A JP H06166828 A JPH06166828 A JP H06166828A JP 4323033 A JP4323033 A JP 4323033A JP 32303392 A JP32303392 A JP 32303392A JP H06166828 A JPH06166828 A JP H06166828A
Authority
JP
Japan
Prior art keywords
group
general formula
formula
coloring
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP4323033A
Other languages
Japanese (ja)
Other versions
JP3173193B2 (en
Inventor
Osayuki Katsuta
修之 勝田
Shinichi Yabushita
伸一 藪下
Shuhei Hashizume
修平 橋爪
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
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Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP32303392A priority Critical patent/JP3173193B2/en
Publication of JPH06166828A publication Critical patent/JPH06166828A/en
Application granted granted Critical
Publication of JP3173193B2 publication Critical patent/JP3173193B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0038—Mixtures of anthraquinones
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

PURPOSE:To obtain a coloring compsn. which can color a hydrophobic material such as a polyester fiber yellow uniformly with a high reproducibility to give a colored article having a high light resistance by incorporating two specific compds. into the coloring compsn. CONSTITUTION:This coloring compsn. contains at least one compd. selected from the grop of compds. of formula I (wherein R1 is 1-4C alkyl, 1-4C alkoxy, or phenyl) and at least one compd. selected from the group of compds. of formula II (wherein R2 and R3 are each H, 1-4C alkyl, or phenyl; and R4 is H or 1-4C alkoxy). The compsn. has a good light resistance, can color a hydrophobic material such as a polyester fiber uniformly with a high reproducibility, and gives a colored article having a high light resistance. When three primary colors are used by using the compsn. as the yellow component, the resulting colored article has an esp. high light resistance.

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【産業上の利用分野】本発明は高耐光着色性組成物およ
びそれを用いる疎水性材料の着色方法に関する。更に詳
しくは、本発明は、例えば、ポリエステル繊維またはそ
の混交品などの疎水性繊維材料を高耐光染色するために
黄色色素として有用な組成物およびその応用に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a highly light-resistant coloring composition and a method for coloring a hydrophobic material using the same. More specifically, the present invention relates to a composition useful as a yellow pigment for highly lightfast dyeing of a hydrophobic fiber material such as polyester fiber or a mixed product thereof, and its application.

【０００２】[0002]

【従来の技術および発明が解決しようとする課題】特開
昭59-51950号公報、同60-239577 号公報、同61-20767号
公報などに、自動車内装材として多用されているポリエ
ステル系繊維材料を高耐光染色することができる染料と
して種々の分散染料組成物が知られている。しかしなが
ら、これらの公知の分散染料組成物を用いてポリエステ
ル繊維またはポリエステル繊維とポリアミド繊維、カチ
オン染料可染型ポリエステル繊維、アセテート繊維、セ
ルロース繊維などとの混交品を染色し、自動車内装用と
して用いると、とりわけ、ポリエステル繊維が極細フィ
ラメント糸、異形断面糸、TiO2などによる艶消し糸など
の加工糸である場合、高温、長時間の露光によって黄色
が褪色し、染色物が変色してしまうという問題が指摘さ
れている。また、これら公知の分散染料は自動車内装用
として高耐光を重点に選定されているため特に起毛品や
極細繊維の染色に要求されている均染性や再現性に問題
が残されている。本発明は、このような問題を解決し、
広く疎水性材料の高耐光着色に有用な組成物を提供する
ものである。BACKGROUND OF THE INVENTION Polyester fiber materials widely used as interior materials for automobiles in Japanese Patent Laid-Open Nos. 59-51950, 60-239577 and 61-20767. Various disperse dye compositions are known as dyes capable of dyeing with high light resistance. However, when dyeing a polyester fiber or a blended product of a polyester fiber and a polyamide fiber, a cationic dye-dyeable polyester fiber, an acetate fiber, a cellulose fiber or the like using these known disperse dye compositions, and using them for automobile interiors In particular, if the polyester fiber is an ultrafine filament yarn, a modified cross-section yarn, or a processed yarn such as a matte yarn made of TiO 2 etc., the problem that the dyed product discolors due to yellow fading due to high temperature and long time exposure Has been pointed out. Further, since these known disperse dyes are selected mainly for high light resistance for automobile interiors, problems remain in the leveling property and reproducibility required for dyeing napped products and ultrafine fibers. The present invention solves such a problem,
It is intended to provide a composition which is widely useful for highly light-resistant coloring of hydrophobic materials.

【０００３】[0003]

【課題を解決するための手段】本発明は下記一般式
（Ｉ）The present invention has the following general formula (I):

【化８】 [Chemical 8]

【０００４】［式中Ｒ1 は、Ｃ1-4 アルキル基、Ｃ1-4
アルコキシ基またはフェニル基を表す。］で示される化
合物群から選ばれる一種以上の化合物および下記一般式
（ＩＩ）[Wherein R 1 is a C 1-4 alkyl group, C 1-4
Represents an alkoxy group or a phenyl group. ] One or more compounds selected from the group of compounds represented by the following general formula (II)

【０００５】[0005]

【化９】 ［式中Ｒ2 およびＲ3 は互いに独立に水素原子、Ｃ1-4
アルキル基またはフェニル基、Ｒ4 は、水素原子または
Ｃ1-4 アルコキシ基を示す。］で示される化合物群から
選ばれる一種以上の化合物を含有して成る高耐光着色性
組成物、およびそれを用いることを特徴とする疎水性材
料の着色方法を提供するものである。前記一般式（Ｉ）
で示される化合物は、例えば、特公昭44-21431号公報お
よび特開昭48-73571号公報などに記載されている公知の
化合物である。また、前記一般式（ＩＩ）で示される化
合物も、C. I. Disperse Yellow （シー． アイ．ジス
パース イエロー）４２、８６などとして公知の化合物
である。本発明の組成物は、一般式（Ｉ）で示される化
合物群から選ばれる少なくとも一種の化合物および一般
式（ＩＩ）で示される化合物群から選ばれる少なくとも
一種の化合物を使用目的に応じて任意の割合で公知の方
法で配合することによって製造することができるが、前
者と後者の配合重量比率は、望ましくは５〜９９：９５
〜１、更に好ましくは２０〜９９：８０〜１である。本
発明の組成物は、色相の調整などの目的で前記一般式
（Ｉ）および（ＩＩ）で示される化合物以外に黄色系分
散染料として知られているアゾ系、キノフタロン系また
はピリドン系などの化合物を含有することができる。ま
た、目的、用途に応じて、分散剤、増量剤、pH調整材、
分散均染剤、ビルダー、染色助剤、溶剤、樹脂バインダ
ーなどを含有することができる。本発明の組成物は、良
好な耐光性を有すると共に、染色において均染性、再現
性に優れた性能を示す組成物として有用である。耐光性
においては、本組成物を黄色成分として三原色使用する
場合に特に良好な性能を示す。三原色使用における青色
成分および／または赤色成分としては、それぞれ分散染
料として公知のアントラキノン系、アゾ系、ヘテロアゾ
系または縮合系のいずれの化合物とも併用することがで
きるが、特にアントラキノン系化合物との三原色使用が
効果的である。好ましい三原色使用として、本発明の組
成物を黄色成分として用い、青色成分として、下記一般
式(III)[Chemical 9] [Wherein R 2 and R 3 are each independently a hydrogen atom, C 1-4
An alkyl group or a phenyl group, R 4 represents a hydrogen atom or a C 1-4 alkoxy group. ] A highly light-resistant coloring composition containing one or more compounds selected from the group of compounds represented by the above, and a method for coloring a hydrophobic material characterized by using the same. The general formula (I)
The compounds represented by are known compounds described in, for example, JP-B-44-21431 and JP-A-48-73571. Further, the compound represented by the general formula (II) is also a compound known as CI Disperse Yellow (C.I. Disperse Yellow) 42, 86 and the like. The composition of the present invention comprises at least one compound selected from the group of compounds represented by the general formula (I) and at least one compound selected from the group of compounds represented by the general formula (II) depending on the purpose of use. The compounding ratio of the former and the latter is preferably 5 to 99:95.
-1 and more preferably 20-99: 80-1. The composition of the present invention is a compound such as an azo-based compound, a quinophthalone-based compound or a pyridone-based compound, which is known as a yellow disperse dye, in addition to the compounds represented by the general formulas (I) and (II) for the purpose of adjusting the hue. Can be included. Also, depending on the purpose and use, a dispersant, a bulking agent, a pH adjusting material,
It may contain a dispersion leveling agent, a builder, a dyeing auxiliary agent, a solvent, a resin binder and the like. INDUSTRIAL APPLICABILITY The composition of the present invention has good light resistance and is useful as a composition that exhibits excellent levelness and reproducibility in dyeing. In terms of light resistance, particularly good performance is exhibited when the present composition uses the three primary colors as the yellow component. The blue component and / or red component in the use of the three primary colors can be used in combination with any of the known anthraquinone-based, azo-based, heteroazo-based or condensation-based compounds as disperse dyes, but especially the use of the three primary colors with the anthraquinone-based compound Is effective. As a preferable three primary colors use, the composition of the present invention is used as a yellow component, and as a blue component, the following general formula (III)

【０００６】[0006]

【化１０】 [Chemical 10]

【０００７】［式中、Ｙ1 およびＹ2 の一方はＯＨ、他
方はＮＨＲ5 を表し、Ｒ5 は例えば、ハロゲン、ヒドロ
キシＣ1-3 アルキル基、Ｃ1-3 アルキルスルホニル基、
Ｃ1-3アルキルカルボニルオキシ基またはフェニルカル
ボニルオキシ基などで置換されていてもよいフェニル基
を表す。］、下記一般式（IV）[In the formula, one of Y 1 and Y 2 represents OH and the other represents NHR 5 , and R 5 is, for example, halogen, hydroxy C 1-3 alkyl group, C 1-3 alkylsulfonyl group,
C 1-3 represents a phenyl group which may be substituted with an alkylcarbonyloxy group or a phenylcarbonyloxy group. ], The following general formula (IV)

【０００８】[0008]

【化１１】 [Chemical 11]

【０００９】［式中、Ｙ3 およびＹ4 の一方はＮＨ2 、
他方はＯＨを、ｎは、１または２を表す。］、下記一般
式（V)[Wherein one of Y 3 and Y 4 is NH 2 ,
The other represents OH and n represents 1 or 2. ], The following general formula (V)

【００１０】[0010]

【化１２】 [Chemical 12]

【００１１】［式中Ｒ6 はＣ1-4 アルコキシ基、Ｃ1-4
アルコキシＣ1-4 アルコキシ基、または、Ｃ1-4 アルコ
キシＣ1-4 アルキル基を表す。］、および下記一般式(V
I)[Wherein R 6 is a C 1-4 alkoxy group, C 1-4
It represents an alkoxy C 1-4 alkoxy group or a C 1-4 alkoxy C 1-4 alkyl group. ], And the following general formula (V
I)

【００１２】[0012]

【化１３】 [Chemical 13]

【００１３】［式中Ｒ7 は、Ｃ1-4 アルキルスルフォニ
ル基、Ｃ1-4 アルコキシカルボニル基またはフェニルオ
キシカルボニル基を表す。］で示される各化合物群から
選ばれる少なくとも一種の化合物、および／または赤色
成分として下記一般式(VII)[In the formula, R 7 represents a C 1-4 alkylsulfonyl group, a C 1-4 alkoxycarbonyl group or a phenyloxycarbonyl group. ] At least one compound selected from each compound group represented by

【００１４】[0014]

【化１４】 [Chemical 14]

【００１５】［式中Ｒ8 は、例えば、ヒドロキシ基、フ
ェノキシカルボニル基またはＣ1-3 アルコキシカルボニ
ルＣ1-3 アルキル基などで置換されていてもよいＣ1-4
アルキル基または、例えば、Ｃ1-3 アルキル基、Ｃ1-3
アルコキシ基、ハロゲン、ヒドロキシ基、Ｃ1-3 アルキ
ルカルボニルオキシ基、Ｃ1-3 アルコキシカルボニルＣ
1-3 アルコキシ基またはＣ1-3 アルコキシＣ1-3 アルキ
ルアミノスルホニル基などで置換されていてもよいフェ
ニル基を表す。］で示される化合物群から選ばれる少な
くとも一種を用いる態様を例示することができる。上記
一般式(III) 〜(VII) で示されるアントラキノン系化合
物はいずれも分散染料として公知の化合物である。本発
明の組成物は、高耐光性分散染料、昇華転写型乾熱記録
用高耐光性色素などとして、ポリエステル、カチオン可
染型ポリエステル、ジアセテート、トリアセテート、ポ
リアミド、ポリカーボネートなどの疎水性材料の着色に
有用である。とりわけ、本発明の組成物は疎水性繊維材
料を染色または捺染する高耐光性黄色系分散染料として
有用である。本発明の組成物を分散染料として用いる場
合、一般式（Ｉ）、一般式(II)で示される化合物は、そ
れぞれ製造工程から得られるウェットケーキに、ナフタ
レンスルホン酸のホルマリン縮合物やリグニンスルホン
酸系などの分散剤の単独あるいは混合物を加えてサンド
ミルなどで微粒化分散して得られるリキッド品、あるい
はそれを乾燥して得られるパウダー品の状態でそれぞれ
所定量を配合してもよいが、染色時、染浴中で配合して
もよい。疎水性繊維材料を染色するにあたっては、本発
明の組成物を水性媒体中に分散させた染色浴に、必要に
応じてpH調整剤、分散均染剤などを加えた後、繊維材料
を浸漬して、加圧下１０５℃以上、好ましくは１１０〜
１４０℃で３０〜６０分間染色する。この染色時間は染
着の状態により短縮または延長することができる。ま
た、ｏ−フェニルフェノールやメチルナフタレンなどの
キャリヤーの存在下で比較的低温、たとえば水の沸騰状
態で染色することもできる。更に、染料分散液を布にパ
ディングした後、１００℃以上でスチーミングや乾熱処
理する染色方法も可能である。捺染の場合は、染料分散
液を適当な糊剤と共に練り合わせ、これを布に印捺した
後、スチーミングまたは乾熱処理を行う。また、インク
ジェット方式によって捺染することもできる。更に耐光
性の優れた染色物を得るため紫外線吸収剤として、たと
えば下記に示すような公知のベンゾトリアゾール系化合
物の一種以上を使用することができる。[Wherein R8 Is, for example, a hydroxy group,
Enoxycarbonyl group or C1-3Alkoxy Carboni
Le C1-3C optionally substituted with an alkyl group or the like1-4 
An alkyl group or, for example, C1-3Alkyl group, C1-3
Alkoxy group, halogen, hydroxy group, C1-3Archi
Lecarbonyloxy group, C1-3Alkoxycarbonyl C
1-3Alkoxy group or C1-3Alkoxy C1-3Archi
Group which may be substituted with, for example, a ruaminosulfonyl group.
Represents a nyl group. ] Selected from the group of compounds represented by
A mode in which at least one kind is used can be exemplified. the above
Anthraquinone compounds represented by the general formulas (III) to (VII)
All of the products are compounds known as disperse dyes. Starting
Ming composition is a high lightfast disperse dye, sublimation transfer type dry heat recording
For high light resistance dyes for use in polyester, cation etc.
Dyed polyester, diacetate, triacetate,
For coloring hydrophobic materials such as Liamide and polycarbonate
It is useful. In particular, the composition of the present invention comprises a hydrophobic fiber material.
As a highly light-resistant yellow disperse dye for dyeing or printing dyes
It is useful. When the composition of the present invention is used as a disperse dye
In general, the compounds represented by the general formula (I) and the general formula (II) are
Each of the wet cakes obtained from the manufacturing process has naphtha
Formalin condensate of lensulfonic acid and lignin sulfone
Add dispersants such as acid-based dispersants individually or as a mixture
Liquid products obtained by atomizing and dispersing with a mill, or
Is a powder product obtained by drying it.
You may add a certain amount, but when dyeing, add it in the dyebath.
Good. When dyeing hydrophobic fiber materials,
If necessary, add the bright composition to a dyebath in an aqueous medium.
After adding pH adjuster, dispersion leveling agent, etc. accordingly, the fiber material
Is immersed, and the pressure is 105 ° C. or higher, preferably 110 to
Stain for 30-60 minutes at 140 ° C. This dyeing time is
It can be shortened or extended depending on the wearing condition. Well
Such as o-phenylphenol and methylnaphthalene
Relatively low temperature in the presence of carrier, eg boiling water
It can also be dyed in a state. In addition, apply the dye dispersion to the cloth.
After baking, steaming or dry heat treatment at 100 ℃ or higher
A dyeing method that can be applied is also possible. In the case of printing, dye dispersion
The liquid was kneaded together with an appropriate sizing agent, and this was printed on a cloth.
After that, steaming or dry heat treatment is performed. Also, ink
It is also possible to print by the jet method. Further light resistance
As an ultraviolet absorber to obtain a dyed product with excellent properties
For example, a known benzotriazole-based compound as shown below
One or more objects can be used.

【００１６】[0016]

【化１５】 このような紫外線吸収剤の使用量は特に制限されない
が、好ましくは被染色物の重量に対し０．５〜５％であ
る。疎水性繊維材料としては、ポリエステル、カチオン
可染型ポリエステル、ジアセテート、トリアセテート、
ポリアミド、ポリカーボネートなどが挙げられる。また
ポリエステル繊維との混交品としては、ポリアミド、ジ
アセテート、カチオン可染型ポリエステル、セルロース
繊維、羊毛、絹との混紡、交織品が挙げられる。本発明
の組成物は、それを分散染料として用いる場合、ポリエ
ステル系繊維材料がポリエスル極細フィラメント糸、異
形断面糸、TiO2などを含む艶けし加工糸などの各種加
工、改質糸であっても、優れた均染性と再現性で優れた
耐光性の染色物を得ることができ、また、ターリング性
においても優れるものである。また、得られた染色物
は、座席シートなどの自動車内装材として用いても、高
温、長時間の露光に十分に耐えるものである。以下、実
施例により本発明を更に詳しく説明する。なお、本文
中、％は重量％を表わす。[Chemical 15] The amount of such an ultraviolet absorber used is not particularly limited, but is preferably 0.5 to 5% with respect to the weight of the material to be dyed. As the hydrophobic fiber material, polyester, cationic dyeable polyester, diacetate, triacetate,
Examples thereof include polyamide and polycarbonate. Examples of the blended product with polyester fiber include polyamide, diacetate, cationic dyeable polyester, cellulose fiber, wool, blended fabric with silk, and woven product. When the composition of the present invention is used as a disperse dye, the polyester-based fiber material may be various modified or modified yarns such as polyester ultrafine filament yarn, modified cross-section yarn, and frosted yarn including TiO 2. It is also possible to obtain a dyed product having excellent levelness and reproducibility and excellent light resistance, and also excellent in terring property. Further, the obtained dyed product can sufficiently withstand exposure to high temperature and long time even when used as an automobile interior material such as a seat. Hereinafter, the present invention will be described in more detail with reference to examples. In the text,% represents% by weight.

【００１７】[0017]

【実施例】【Example】

実施例１ 下記式（１） Example 1 The following formula (1)

【００１８】[0018]

【化１６】 [Chemical 16]

【００１９】の化合物１５０ｇと下記式（２）150 g of the compound of the formula (2)

【００２０】[0020]

【化１７】 [Chemical 17]

【００２１】の化合物１５０ｇを、ナフタレンスルホン
酸ソーダのホルマリン縮合物３００ｇと共に、６００ｇ
の水中でサンドミルにより微粒化し次いでリグニンスル
ホン酸３５０ｇを加えた後、噴霧乾燥した。乾燥品とし
て、化合物（１）１５％、（２）１５％を含み、アニオ
ン系分散剤６５％、水分５％から成る黄色分散染料組成
物を得た。本組成物５ｇを水１０００ｍｌに分散させ、
酢酸と酢酸ナトリウムを添加してｐＨ５に調整し、染浴
を作成した。この染浴にテトロントロピカル（ポリエス
テル布東レ（株）製品）１００ｇを浸し、６０℃から１
分間に１℃の割合で昇温し、１３０℃で６０分間染色し
た。ついで染色物をカセイソーダ３ｇ、ハイドロサルフ
ァイト３ｇ、ベタイン型両性界面活性剤３ｇと水３００
０ｇからなる処理液で、８５℃で１０分間還元洗浄処理
を行い、水洗、乾燥したところ、均一で濃厚な黄色の染
色物が再現性良く得られた。耐光堅牢度は、染色布にウ
レタンフォームを裏打ちし、カーボンアークフェードメ
ーター（スガ試験機ロングライフタイプ）中で８３℃
６００時間照射した後、ＪＩＳ Ｌ ０８０４−１９６
５変褪色用グレースケールにて判定したところ、４級と
良好な値を示した。600 g of the compound of 150 g together with 300 g of formalin condensate of sodium naphthalene sulfonate
After being atomized by a sand mill in water, the solution was added with 350 g of ligninsulfonic acid, and then spray-dried. As a dried product, a yellow disperse dye composition containing 15% of the compound (1) and 15% of (2), 65% of an anionic dispersant, and 5% of water was obtained. Disperse 5 g of the composition in 1000 ml of water,
The pH was adjusted to 5 by adding acetic acid and sodium acetate to prepare a dye bath. 100 g of Tetron Tropical (a polyester cloth Toray Co., Ltd. product) is soaked in this dyeing bath and the temperature is raised from 60 ° C. to 1
The temperature was raised at a rate of 1 ° C. per minute, and dyeing was performed at 130 ° C. for 60 minutes. Then, the dyed product is 3 g of caustic soda, 3 g of hydrosulfite, 3 g of a betaine-type amphoteric surfactant and 300 parts of water.
When 0 g of the treatment liquid was subjected to reduction washing treatment at 85 ° C. for 10 minutes, washing with water and drying, a uniform and deep yellow dyed product was obtained with good reproducibility. The light fastness is 83 ° C in a carbon arc fade meter (Suga tester long life type) with a urethane cloth lining on a dyed cloth.
After irradiation for 600 hours, JIS L 0804-196
Judgment was carried out using a gray scale for 5 discoloration and fading, which was a good value of 4th grade.

【００２２】実施例２ 実施例１で得られた黄色分散染料組成物１．８ｇと下記
式（３）Example 2 1.8 g of the yellow disperse dye composition obtained in Example 1 and the following formula (3)

【００２３】[0023]

【化１８】 [Chemical 18]

【００２４】で示される青色分散染料1.35g （染料原体
30％とアニオン系分散剤からなるビルダーを含む分散染
料調合物）、下記式（４）1.35 g of the blue disperse dye represented by
Disperse dye preparation containing a builder consisting of 30% and an anionic dispersant), the following formula (4)

【００２５】[0025]

【化１９】 で示される赤色分散染料2.5g（染料原体30％とアニオン
系分散剤からなるビルダーを含む分散染料調合物）を染
浴中に配合し、水1000mlに分散させ、酢酸と酢酸ナトリ
ウムを添加してpH５に調整し、染浴を作成した。この染
浴にテトロントロピカル（ポリエステル東レ（株）製
品）100gを浸し、実施例１と同様に染色し、得られた染
色物は焦げ茶色に均一に再現性良く染色された。比較例
として、式（１）の化合物３００ｇとナフタレンスルホ
ン酸ソーダのホルマリン縮合物３００ｇを６００ｇの水
中で微粒化し、次いでリグンスルホン酸３５０ｇを加え
た後、噴霧乾燥して染料調合物を得た。同様に式（２）
の化合物についても微粒化後、乾燥して仕上げた。それ
ぞれ化合物３０％を含む分散染料調合物を得た。本分散
染料調合物を使用し、表２の実施例と同様に三原色配合
染色を行い、染色布を得た。得られた各染色布にウレタ
ンフォームを裏打ちし、３１０ｎｍ以下の光を遮断する
紫外線カットフィルターを、試料表面から１ｃｍのとこ
ろに取り付けたものをキセノンフェードメータ（ブラッ
クパネル温度８９℃）で７５０ｋＪ照射し（検出波長34
0nm ）、JIS L 0804-1965 変褪色用グレースケールで判
定すると、表１に示すように実施例２の染色布の耐光堅
牢度は、比較例１および比較例２に比べ、著しく優れて
いた。[Chemical 19] 2.5 g of a red disperse dye represented by (a disperse dye composition containing a builder consisting of a dye base of 30% and an anionic dispersant) was mixed in a dye bath, dispersed in 1000 ml of water, and acetic acid and sodium acetate were added. Then, the pH was adjusted to 5 to prepare a dye bath. 100 g of Tetron Tropical (a product of Polyester Toray Co., Ltd.) was dipped in this dyebath and dyed in the same manner as in Example 1. The obtained dyed product was dyed dark brown uniformly and with good reproducibility. As a comparative example, 300 g of the compound of formula (1) and 300 g of formalin condensate of sodium naphthalene sulfonate were atomized in 600 g of water, 350 g of lignosulfonic acid was added, and then spray-dried to obtain a dye preparation. Similarly, equation (2)
The compound (2) was also atomized and then dried and finished. Disperse dye formulations were obtained, each containing 30% of the compound. Using this disperse dye composition, the three primary color compounding dyeings were carried out in the same manner as in the examples of Table 2 to obtain dyed fabrics. Each of the obtained dyed cloths was lined with urethane foam, and an ultraviolet cut filter for blocking light of 310 nm or less was attached at a position 1 cm from the sample surface, and 750 kJ was irradiated with a xenon fade meter (black panel temperature 89 ° C). (Detection wavelength 34
0 nm), JIS L 0804-1965 Judging from the gray scale for fading, as shown in Table 1, the light fastness of the dyed fabric of Example 2 was significantly superior to that of Comparative Examples 1 and 2.

【００２６】[0026]

【表１】 [Table 1]

【００２７】実施例３〜７ 化合物（１）、（２）、（３）、（４）および下記式
（５）、（６）の化合物についてそれぞれ３０％を含有
する分散染料調合物を作成し、ポリエステル起毛布（帝
人（株）製）１００ｇを、実施例２と同様にして、表２
に示す組合せ処方で染色した。染色物はすべて斑のない
均一な染色物として得られ、その耐光性は表２に示すよ
うに著しく良好であった。Examples 3 to 7 Disperse dye formulations containing 30% of each of the compounds (1), (2), (3) and (4) and the compounds of the following formulas (5) and (6) were prepared. 100 g of polyester brushed cloth (manufactured by Teijin Limited) was used in the same manner as in Example 2 and Table 2
It dye | stained by the combination prescription shown in. All the dyed products were obtained as a uniform dyed product without spots, and the light fastness thereof was remarkably good as shown in Table 2.

【００２８】[0028]

【化２０】 [Chemical 20]

【００２９】（Ｘ、Ｙの一方がＮＨ2 、他方がＯＨの混
合物）(A mixture of NH 2 in one of X and Y and OH in the other)

【００３０】[0030]

【化２１】 [Chemical 21]

【００３１】[0031]

【表２】 [Table 2]

【００３２】実施例８〜９ 化合物（１）、（２）、（３）、（４）、（５）をそれ
ぞれ３０％含有する分散染料調合物と、式（７）で示さ
れる紫外線吸収剤分散液（紫外線吸収剤４０％、アニオ
ン系分散剤２０％、水４０％から成る混合物）Examples 8 to 9 Disperse dye preparations containing 30% each of the compounds (1), (2), (3), (4) and (5), and an ultraviolet absorber represented by the formula (7). Dispersion (mixture of 40% UV absorber, 20% anionic dispersant, 40% water)

【００３３】[0033]

【化２２】 [Chemical formula 22]

【００３４】を用い、表３に示す配合処方にてポリエス
テル起毛布１００ｇを実施例２と同様にして染色した。
式（７）で示す紫外線吸収剤分散液は、染浴作成時に２
ｇ添加した。比較例３、４として式（１）または（２）
の黄色分散染料のいずれか一種を省いて染色した染色物
を用いて比較した。実施例２と同様に耐光堅牢度試験を
したところ、表３に示すように、実施例８、９の染色布
の耐光堅牢度は、比較例３および比較例４に比べ、著し
く優れていた。100 g of polyester napped cloth was dyed in the same manner as in Example 2 by using the above and the formulation shown in Table 3.
The ultraviolet absorber dispersion liquid represented by the formula (7) is used when the dye bath is prepared.
g was added. Formulas (1) or (2) as Comparative Examples 3 and 4
Comparison was made using a dyed product obtained by omitting any one of the yellow disperse dyes. When the light fastness test was conducted in the same manner as in Example 2, as shown in Table 3, the light fastness of the dyed fabrics of Examples 8 and 9 was remarkably excellent as compared with Comparative Examples 3 and 4.

【００３５】[0035]

【表３】 [Table 3]

【００３６】実施例１０ 実施例９における式（２）のかわりに下記式（８）Example 10 Instead of the equation (2) in the example 9, the following equation (8) was used.

【００３７】[0037]

【化２３】 [Chemical formula 23]

【００３８】で示す化合物３０％を含有する分散染料調
合物を用い、実施例９と同様にして染色し、ベージュ色
の均一な染色物を得た。本染色布は、実施例２と同様に
耐光性を測定したところ、耐光堅牢度４−５級と良好な
結果を示した。Dyeing was carried out in the same manner as in Example 9 using the disperse dye preparation containing 30% of the compound shown in (3) to obtain a beige uniform dyeing product. When the light resistance of this dyed fabric was measured in the same manner as in Example 2, the light fastness was 4-5, which was a good result.

【００３９】実施例11〜14 実施例４中の式（１）の染料の代わりに表４に示す染料
調合物（化合物として３０％含有）を用いて、実施例４
同様の方法で染色し、エンジ色の染色物を得た。実施例
２と同様に耐光堅牢度試験をしたところ、表４に示すよ
うに実施例１１〜１４の染色布の耐光堅牢度は、優れた
ものであった。Examples 11 to 14 Using the dye formulations shown in Table 4 (containing 30% as compound) instead of the dye of the formula (1) in Example 4, Example 4
Dyeing was carried out in the same manner as above to obtain a dyed product of the color red. When a light fastness test was conducted in the same manner as in Example 2, as shown in Table 4, the dyed fabrics of Examples 11 to 14 were excellent in light fastness.

【００４０】[0040]

【表４】 [Table 4]

【００４１】実施例１５〜２３ 実施例４中の式（４）の染料の代わりに表５に示す染料
調合物（化合物として３０％含有）を用い、更に下記式
（９）Examples 15 to 23 Dye formulations shown in Table 5 (containing 30% as a compound) were used in place of the dye of the formula (4) in Example 4, and the following formula (9) was used.

【００４２】[0042]

【化２４】 [Chemical formula 24]

【００４３】に示す紫外線吸収剤分散液２g （紫外線吸
収剤４０％、アニオン系分散剤４０％、水２０％から成
る混合物）を併用し、実施例４と同様の方法で染色し、
エンジ色の染色物を得た。実施例２と同様に耐光堅牢度
試験をしたところ、表５に示すように実施例１５〜２３
の染色布の耐光堅牢度は、優れたものであった。Dyeing was carried out in the same manner as in Example 4 using together 2 g of the ultraviolet absorbent dispersion shown in (a mixture of 40% ultraviolet absorbent, 40% anionic dispersant and 20% water).
An orange dyed product was obtained. When a light fastness test was conducted in the same manner as in Example 2, Examples 15 to 23 as shown in Table 5 were obtained.
The fastness to light of the dyed fabric was excellent.

【００４４】[0044]

【表５】 [Table 5]

【００４５】実施例２４〜３３ 実施例３中の式（３）の染料の代わりに表６に示す染料
調合物（化合物として３０％含有）を用い、更に式
（７）紫外線吸収剤分散液２ｇを併用し、実施例２と同
様の方法で染色し、アイボリー色の染色物を得た。実施
例２と同様に耐光堅牢度試験をしたところ、表６に示す
ように実施例２４〜３３の染色布の耐光堅牢度は、優れ
たものであった。Examples 24 to 33 Dye formulations shown in Table 6 (containing 30% as a compound) were used in place of the dye of the formula (3) in Example 3, and 2 g of the ultraviolet absorber dispersion of the formula (7) was used. Was also used in the same manner as in Example 2 to obtain an ivory dyed product. When a light fastness test was conducted in the same manner as in Example 2, as shown in Table 6, the dyed cloths of Examples 24 to 33 were excellent in light fastness.

【００４６】[0046]

【表６】 [Table 6]

【００４７】実施例３４ 実施例１で示される黄色染料組成物０．６ｇと、式
（５）で示される化合物３０％を含有する青色分散染料
調合物０．５ｇ、式（６）で示される化合物３０％を含
有する赤色分散染料調合物１．５ｇ、更にＣ．Ｉ．Ｂａ
ｓｉｃ Ｙｅｌｌｏｗ ７３ ０．１５ｇ、Ｃ．Ｉ．Ｂ
ａｓｉｃ Ｒｅｄ ４６ ０．２５ｇ、Ｃ．Ｉ．Ｂａｓ
ｉｃ Ｂｌｕｅ １２９ ０．０５ｇを１０００ｍｌの
水に分散させ、化合物（７）で示される紫外線吸収剤分
散液２ｇ、芒硝５ｇおよび酢酸、酢酸ナトリウムを添加
してｐＨ３．５に調整し、染浴を作成した。この染浴に
ポリエステル５０％、カチオン可染型ポリエステル５０
％からなるニット布１００ｇを投入し、室温から１２５
℃まで２℃／分で昇温した。１２５℃で６０分保温した
後、除冷して染色を終了させた。染色物を水洗、ソーピ
ング（非イオン活性剤１ｇ／Ｌ ８０℃、２分）し、乾
燥して仕上げた染色物は濃淡のあるエンジ色に染色さ
れ、実施例２の方法による耐光堅牢度は４級と良好であ
った。Example 34 0.6 g of the yellow dye composition of Example 1 and 0.5 g of a blue disperse dye formulation containing 30% of the compound of formula (5), of formula (6). 1.5 g of a red disperse dye formulation containing 30% of the compound, further C.I. I. Ba
sic Yellow 73 0.15 g, C.I. I. B
asic Red 46 0.25 g, C.I. I. Bas
Disperse 0.05 g of ic Blue 129 in 1000 ml of water, add 2 g of the ultraviolet absorbent dispersion represented by the compound (7), 5 g of Glauber's salt, and adjust the pH to 3.5 by adding acetic acid and sodium acetate to prepare a dye bath. did. 50% polyester and 50% cationic dyeable polyester in this dye bath
100 g of 100% knit cloth was added, and the temperature was changed from room temperature to 125
The temperature was raised to 2 ° C / min. After keeping the temperature at 125 ° C. for 60 minutes, it was cooled to finish the dyeing. The dyed product is washed with water, soaped (nonionic surfactant 1 g / L, 80 ° C., 2 minutes), and dried to give a dyed product having a dark red shade, and the light fastness according to the method of Example 2 is 4 The grade was good.

Claims (4)

【特許請求の範囲】[Claims] 【請求項１】下記一般式（Ｉ） 【化１】 ［式中Ｒ1 は、Ｃ1-4 アルキル基、Ｃ1-4 アルコキシ基
またはフェニル基を表す。］で示される化合物群から選
ばれる一種以上の化合物および下記一般式（ＩＩ） 【化２】 ［式中Ｒ2 およびＲ3 は互いに独立に水素原子、Ｃ1-4
アルキル基またはフェニル基、Ｒ4 は水素原子またはＣ
1-4 アルコキシ基を示す。］で示される化合物群から選
ばれる一種以上の化合物を含有して成る高耐光着色性組
成物。1. The following general formula (I): [In the formula, R 1 represents a C 1-4 alkyl group, a C 1-4 alkoxy group or a phenyl group. ] One or more compounds selected from the group of compounds represented by the following general formula (II) [Wherein R 2 and R 3 are each independently a hydrogen atom, C 1-4
Alkyl group or phenyl group, R 4 is hydrogen atom or C
1-4 represents an alkoxy group. ] A highly light-resistant coloring composition comprising one or more compounds selected from the group of compounds represented by: 【請求項２】一般式（Ｉ）で示される化合物群から選ば
れる一種以上の化合物５〜99重量％および一般式（II）
で示される化合物群から選ばれる一種以上の化合物95〜
１重量％含有してなる請求項１に記載の組成物。2. 5-99% by weight of one or more compounds selected from the group of compounds represented by general formula (I) and general formula (II)
One or more compounds selected from the group of compounds represented by 95 ~
The composition according to claim 1, which comprises 1% by weight. 【請求項３】請求項１に記載の組成物を用いることを特
徴とする疎水性材料の着色方法。3. A method for coloring a hydrophobic material, which comprises using the composition according to claim 1. 【請求項４】黄色成分として請求項１に記載の組成物を
用い、青色成分として、下記一般式(III) 【化３】 ［式中、Ｙ1 およびＹ2 の一方はOH、他方はＮＨＲ5 を
表し、Ｒ5 は置換されていてもよいフェニル基を表
す。］、下記一般式（IV） 【化４】 ［式中、Ｙ3 およびＹ4 の一方はＮＨ2 、他方はＯＨ
を、ｎは１または２を表す。］、下記一般式（V) 【化５】 ［式中Ｒ6 はＣ1-4 アルコキシ基、Ｃ1-4 アルコキシＣ
1-4 アルコキシ基または、Ｃ1-4 アルコキシＣ1-4 アル
キル基を表す。］、および下記一般式(VI) 【化６】 ［式中Ｒ7 は、Ｃ1-4 アルキルスルフォニル基、Ｃ1-4
アルコキシカルボニル基またはフェニルオキシカルボニ
ル基を表す。］で示される各化合物群から選ばれる少な
くとも一種の化合物、および／または赤色成分として下
記一般式(VII) 【化７】 ［式中Ｒ8 は置換されていてもよいＣ1-4 アルキル基ま
たは、置換されていてもよいフェニル基を表す。］で示
される化合物群から選ばれる少なくとも一種を用いる請
求項３に記載の着色方法。4. The composition according to claim 1 is used as a yellow component, and the following general formula (III): [In the formula, one of Y 1 and Y 2 represents OH, the other represents NHR 5 , and R 5 represents an optionally substituted phenyl group. ], The following general formula (IV): [Wherein one of Y 3 and Y 4 is NH 2 and the other is OH
And n represents 1 or 2. ], The following general formula (V): [Wherein R 6 is a C 1-4 alkoxy group, a C 1-4 alkoxy C
It represents a 1-4 alkoxy group or a C 1-4 alkoxy C 1-4 alkyl group. ] And the following general formula (VI): [In the formula, R 7 represents a C 1-4 alkylsulfonyl group, C 1-4
Represents an alkoxycarbonyl group or a phenyloxycarbonyl group. ] At least one compound selected from each compound group represented by the following general formula (VII) [In the formula, R 8 represents an optionally substituted C 1-4 alkyl group or an optionally substituted phenyl group. ] The coloring method of Claim 3 which uses at least 1 type selected from the compound group shown by these.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001342375A (en) * 2000-06-02 2001-12-14 Kiwa Kagaku Kogyo Kk Highly light resistant dye composition and dying method using the same
WO2005071016A3 (en) * 2004-01-21 2005-11-17 Ciba Sc Holding Ag Dye mixtures
CN103228740A (en) * 2010-11-19 2013-07-31 日本化药株式会社 Disperse dye and method for dyeing hydrophobic fiber material using same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001342375A (en) * 2000-06-02 2001-12-14 Kiwa Kagaku Kogyo Kk Highly light resistant dye composition and dying method using the same
JP4493160B2 (en) * 2000-06-02 2010-06-30 紀和化学工業株式会社 High light fast dye composition and dyeing method using the same
WO2005071016A3 (en) * 2004-01-21 2005-11-17 Ciba Sc Holding Ag Dye mixtures
JP2008527052A (en) * 2004-01-21 2008-07-24 チバ ホールディング インコーポレーテッド Dye mixture
CN103228740A (en) * 2010-11-19 2013-07-31 日本化药株式会社 Disperse dye and method for dyeing hydrophobic fiber material using same

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