JP4470646B2 - Disperse dye composition and method for coloring hydrophobic material using the same - Google Patents
Disperse dye composition and method for coloring hydrophobic material using the same Download PDFInfo
- Publication number
- JP4470646B2 JP4470646B2 JP2004243417A JP2004243417A JP4470646B2 JP 4470646 B2 JP4470646 B2 JP 4470646B2 JP 2004243417 A JP2004243417 A JP 2004243417A JP 2004243417 A JP2004243417 A JP 2004243417A JP 4470646 B2 JP4470646 B2 JP 4470646B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- disperse dye
- carbon atoms
- dye composition
- yellow
- 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.)
- Expired - Fee Related
Links
Landscapes
- Coloring (AREA)
Description
本発明は、疎水性繊維材料を着色する際に、耐光堅牢度に優れた着色物を与える分散染料組成物に関する。 The present invention relates to a disperse dye composition that gives a colored product having excellent light fastness when coloring a hydrophobic fiber material.
下式（Ｉ）で示される黄色分散染料は、Ｃ．Ｉ．Ｄｉｓｐｅｒｓｅ Ｙｅｌｌｏｗ５１等として公知の染料である。
［式中、Ｒ１は炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基又はフェニル基を表す。該フェニル基における水素原子は、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ハロゲン原子、水酸基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数３〜７のアルコキシカルボニルアルコキシ基及び炭素数２〜６のアルコキシアルキルアミノスルホニル基からなる群より選ばれる置換基で置換されていてもよい。］
The yellow disperse dye represented by the following formula (I) is C.I. I. It is a dye known as Disperse Yellow 51 or the like.
[Wherein, R 1 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group. The hydrogen atom in the phenyl group is an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, a hydroxyl group, an alkylcarbonyloxy group having 2 to 4 carbon atoms, or an alkoxycarbonyl having 3 to 7 carbon atoms. It may be substituted with a substituent selected from the group consisting of an alkoxy group and an alkoxyalkylaminosulfonyl group having 2 to 6 carbon atoms. ]
上式（Ｉ）で示される黄色分散染料は、耐光堅牢度に優れた着色物を与える分散染料である。そして、該染料（Ｉ）とモノアゾベンゼン系の黄橙色分散染料を配合して得た黄色分散染料組成物、及び、該黄色分散染料組成物にアミノアントラキノン系の赤色分散染料の単独又は混合物を配合したベージュ、ブラウンやエンジ色等の分散染料組成物が特許文献１に記載されている（特許文献１の第３頁を参照）。 The yellow disperse dye represented by the above formula (I) is a disperse dye that gives a colored product having excellent light fastness. A yellow disperse dye composition obtained by blending the dye (I) with a monoazobenzene-based yellow-orange disperse dye, and an aminoanthraquinone-based red disperse dye alone or in a mixture with the yellow disperse dye composition A beige, brown, or engineered disperse dye composition is described in Patent Document 1 (see page 3 of Patent Document 1).
しかしながら、上述した特許文献１記載の黄色分散染料（Ｉ）とモノアゾベンゼン系の黄橙色分散染料を配合して得た黄色の分散染料組成物は、青色分散染料及び／又は赤色分散染料と配合して三原色用の分散染料組成物とすると、該三原色用の分散染料組成物から得られる着色物の耐光堅牢度が必ずしも満足できるものではなかった。また、前記の黄色分散染料（Ｉ）は、それ自体ポリエステル繊維等の疎水性繊維材料に対する染着性が低いという問題があった。 However, a yellow disperse dye composition obtained by blending the yellow disperse dye (I) described in Patent Document 1 and a monoazobenzene-based yellow-orange disperse dye is blended with a blue disperse dye and / or a red disperse dye. When the disperse dye composition for the three primary colors is used, the light fastness of the colored product obtained from the disperse dye composition for the three primary colors is not always satisfactory. In addition, the yellow disperse dye (I) itself has a problem of low dyeability to hydrophobic fiber materials such as polyester fibers.
本発明の目的は、疎水性繊維材料に対する染着性と着色物の耐光堅牢度とが改良された黄色分散染料組成物、並びに、該黄色分散染料組成物に青色分散染料及び／又は赤色分散染料を配合した三原色用の分散染料組成物を提供することにある。 An object of the present invention is to provide a yellow disperse dye composition having improved dyeability to hydrophobic fiber materials and light fastness of coloring matter, and a blue disperse dye and / or a red disperse dye in the yellow disperse dye composition Is to provide a disperse dye composition for the three primary colors.
すなわち、本発明（イ）は、下式（Ｉ）で示される分散染料及び下式（ＩＩ）で示される分散染料を含有してなる黄色分散染料組成物を提供するものである。
［式中、Ｒ１は炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基又はフェニル基を表す。該フェニル基における水素原子は、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ハロゲン原子、水酸基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数３〜７のアルコキシカルボニルアルコキシ基及び炭素数２〜６のアルコキシアルキルアミノスルホニル基からなる群より選ばれる置換基で置換されていてもよい。］
That is, the present invention (I) provides a yellow disperse dye composition comprising a disperse dye represented by the following formula (I) and a disperse dye represented by the following formula (II).
[Wherein, R 1 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group. The hydrogen atom in the phenyl group is an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, a hydroxyl group, an alkylcarbonyloxy group having 2 to 4 carbon atoms, or an alkoxycarbonyl having 3 to 7 carbon atoms. It may be substituted with a substituent selected from the group consisting of an alkoxy group and an alkoxyalkylaminosulfonyl group having 2 to 6 carbon atoms. ]
また、本発明（ロ）は、耐光堅牢度が５級以上の青色分散染料及び／又は耐光堅牢度が５級以上の赤色分散染料と、上記（イ）の黄色分散染料組成物とを含む三原色用分散染料組成物を提供するものである。但し、上記の耐光堅牢度は、ＪＩＳ Ｌ０８０８標準染色濃度表３号に定められた表面濃度に染色したポリエステル布を用いて、ＪＩＳ Ｌ−０８４２に規定される試験法で測定するものとする。
さらに、本発明（ハ）は、上記（イ）の黄色分散染料組成物又は上記（ロ）の三原色用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着色方法を提供するものである。
In addition, the present invention (b) includes three primary colors including a blue disperse dye having a light fastness level of 5 or higher and / or a red disperse dye having a light fastness level of 5 or higher and the yellow disperse dye composition of (i) above. Disperse dye compositions are provided. However, the light fastness is measured by a test method defined in JIS L-0842 using a polyester cloth dyed to the surface concentration specified in JIS L0808 Standard Dyeing Density Table 3.
Furthermore, the present invention (c) provides a method for coloring a hydrophobic fiber material, characterized by using the yellow disperse dye composition of (i) above or the disperse dye composition for three primary colors of (b) above. is there.
本発明（イ）の黄色分散染料組成物は、青色分散染料及び／又は赤色分散染料と配合して三原色用の分散染料組成物とした際に、疎水性繊維材料に対する染着性が改良される。
また、本発明（ロ）及び（ハ）によれば、着色された疎水性繊維材料の耐光堅牢度が良好である。
When the yellow disperse dye composition of the present invention (a) is blended with a blue disperse dye and / or a red disperse dye to form a disperse dye composition for three primary colors, the dyeing property to a hydrophobic fiber material is improved. .
Moreover, according to this invention (b) and (c), the light fastness of the colored hydrophobic fiber material is favorable.
以下、本発明を詳細に説明する。
本発明における分散染料（Ｉ）及び（ＩＩ）は、特公昭４４−２１４３１号公報や特開昭４８−７３５７１号公報等に記載された化合物である。
分散染料（Ｉ）におけるＲ１は、メチル基、エチル基、プロピル基やブチル基のような炭素数１〜４のアルキル基；メトキシ基、エトキシ基、プロポキシ基やブトキシ基のような炭素数１〜４のアルコキシ基；フェニル基を表す。該フェニル基の水素原子は置換基で置換されていてもよい。該置換基としては、例えば、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ハロゲン原子、水酸基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数３〜７のアルコキシカルボニルアルコキシ基及び炭素数２〜６のアルコキシアルキルアミノスルホニル基等からなる群より選ばれる。
Hereinafter, the present invention will be described in detail.
The disperse dyes (I) and (II) in the present invention are compounds described in JP-B Nos. 44-21431 and 48-73571.
R 1 in the disperse dye (I) is an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group or a butyl group; 1 carbon atom such as a methoxy group, an ethoxy group, a propoxy group or a butoxy group. -4 alkoxy group; represents a phenyl group. The hydrogen atom of the phenyl group may be substituted with a substituent. Examples of the substituent include an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, a hydroxyl group, an alkylcarbonyloxy group having 2 to 4 carbon atoms, and an alkoxycarbonyl having 3 to 7 carbon atoms. It is selected from the group consisting of an alkoxy group and an alkoxyalkylaminosulfonyl group having 2 to 6 carbon atoms.
分散染料（Ｉ）における好ましいＲ１は、メチル基、エチル基、メトキシ基、エトキシ基又はフェニル基である。
本発明における黄色分散染料組成物は、分散染料（Ｉ）と分散染料（ＩＩ）を任意の割合で配合することによって調製することができる。上記の黄色分散染料組成物における分散染料（Ｉ）と分散染料（ＩＩ）の好ましい重量割合は（９９．９：０．１）〜（５０．０：５０．０）の範囲であり、より好ましい重量割合は（９９．８：０．２）〜（７０．０：３０．０）の範囲であり、特に好ましい重量割合は（９９．５：０．５）〜（７０．０：３０．０）の範囲である。
本発明の黄色分散染料組成物は、アゾ系分散染料、キノフタロン系分散染料やピリドン系分散染料等を含有してもよい。また、上記の黄色分散染料組成物は、分散剤、増量剤、ｐＨ調整剤、分散均染剤、ビルダー、染色助剤、溶剤や樹脂バインダー等を含有してもよい。
Preferred R 1 in the disperse dye (I) is a methyl group, an ethyl group, a methoxy group, an ethoxy group or a phenyl group.
The yellow disperse dye composition in the present invention can be prepared by blending disperse dye (I) and disperse dye (II) in an arbitrary ratio. The preferred weight ratio of the disperse dye (I) and the disperse dye (II) in the yellow disperse dye composition is in the range of (99.9: 0.1) to (50.0: 50.0), and more preferred. The weight ratio is in the range of (99.8: 0.2) to (70.0: 30.0), and the particularly preferred weight ratio is (99.5: 0.5) to (70.0: 30.0). ).
The yellow disperse dye composition of the present invention may contain an azo disperse dye, a quinophthalone disperse dye, a pyridone disperse dye, and the like. The yellow disperse dye composition may contain a dispersant, an extender, a pH adjuster, a dispersion leveling agent, a builder, a dyeing assistant, a solvent, a resin binder, and the like.
本発明の黄色分散染料組成物は、得られた着色物が良好な耐光堅牢度を示すばかりでなく、着色時の均染性や再現性に優れている。上述した着色物の耐光堅牢度は、本発明の黄色分散染料組成物を三原色用分散染料組成物の黄色成分として使用する場合に特に良好である。上記の三原色用分散染料組成物における青色成分及び／又は赤色成分として使用し得る分散染料としては、ポリエステル布をＪＩＳ Ｌ０８０８標準染色濃度表３号に定められた表面濃度に染色した布を用いて、ＪＩＳ Ｌ−０８４２に規定される耐光堅牢度試験法を実施し、該耐光堅牢度が５級以上を示す青色分散染料及び／又は耐光堅牢度が５級以上を示す赤色分散染料を用いることが好ましい。上記の耐光堅牢度が５級以上である分散染料は、アントラキノン系分散染料、ピリジンアゾ系分散染料、ナフタル酸イミドアゾ系分散染料、アゾ系分散染料、ヘテロアゾ系分散染料や縮合系分散染料等から選択される。
本発明において、黄色分散染料組成物と共に使用し得る青色分散染料及び赤色分散染料を以下に例示する。
In the yellow disperse dye composition of the present invention, not only the obtained colored product exhibits good light fastness but also excellent leveling and reproducibility during coloring. The light fastness of the above-described colored product is particularly good when the yellow disperse dye composition of the present invention is used as the yellow component of the three primary color disperse dye composition. As a disperse dye that can be used as a blue component and / or a red component in the disperse dye composition for the three primary colors described above, using a fabric dyed polyester fabric to a surface concentration defined in JIS L0808 Standard Dye Density Table 3, It is preferable to carry out the light fastness test method specified in JIS L-0842 and use a blue disperse dye having a light fastness of 5 or higher and / or a red disperse dye having a light fastness of 5 or higher. . The disperse dye having a light fastness of 5 or higher is selected from anthraquinone disperse dyes, pyridine azo disperse dyes, naphthalic acid imide azo disperse dyes, azo disperse dyes, heteroazo disperse dyes, condensation disperse dyes, and the like. The
Examples of the blue disperse dye and the red disperse dye that can be used with the yellow disperse dye composition in the present invention are given below.
［青色分散染料］
［式中、Ｙ１及びＹ２の一方は水酸基を表し、他方は−ＮＨＲ２を表す。Ｒ２はハロゲン原子、炭素数１〜３のヒドロキシアルキル基、炭素数１〜３のアルキルスルホニル基、炭素数２〜４のアルキルカルボニルオキシ基又はフェニル基を表す。該フェニル基における水素原子はフェニルカルボニルオキシ基で置換されていてもよい。］
[Blue disperse dye]
[Wherein, one of Y 1 and Y 2 represents a hydroxyl group, and the other represents —NHR 2 . R 2 represents a halogen atom, a hydroxyalkyl group having 1 to 3 carbon atoms, an alkylsulfonyl group having 1 to 3 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, or a phenyl group. The hydrogen atom in the phenyl group may be substituted with a phenylcarbonyloxy group. ]
［式中、Ｙ３及びＹ４の一方はアミノ基を表し、他方は水酸基を表す。ｎは０、１又は２を表す。
Ｒ３は水素原子、炭素数１〜３のアルコキシ基又はフェニル基を表す。該フェニル基における水素原子は、ヒドロキシ基、炭素数１〜３のアルコキシ基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数２〜４のアルコキシカルボニルオキシ基及びフェニルカルボニルオキシ基からなる群より選ばれる置換基で置換されていてもよい。］
[Wherein, one of Y 3 and Y 4 represents an amino group, and the other represents a hydroxyl group. n represents 0, 1 or 2.
R 3 represents a hydrogen atom, an alkoxy group having 1 to 3 carbon atoms, or a phenyl group. The hydrogen atom in the phenyl group is selected from the group consisting of a hydroxy group, an alkoxy group having 1 to 3 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyloxy group having 2 to 4 carbon atoms, and a phenylcarbonyloxy group. It may be substituted with a selected substituent. ]
［式中、Ｒ４は炭素数１〜５のアルキル基、炭素数１〜５のアルコキシ基、炭素数３〜１２のアルコキシアルコキシアルキル基又は炭素数２〜８のアルコキシアルキル基を表す。］ [Wherein, R 4 represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxyalkoxyalkyl group having 3 to 12 carbon atoms, or an alkoxyalkyl group having 2 to 8 carbon atoms. ]
［式（ＶＩ）中、ベンゼン環の炭素原子に結合するＲ５は水素原子、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、炭素数１〜３のヒドロキシアルキル基、炭素数１〜４のアルキルスルホニル基、炭素数２〜５のアルキルカルボニルオキシ基、フェニルカルボニルオキシ基又は炭素数７〜９のアルキルフェニルスルホニル基を表す。］ [In formula (VI), R 5 bonded to the carbon atom of the benzene ring is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyalkyl group having 1 to 3 carbon atoms, carbon An alkylsulfonyl group having 1 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 5 carbon atoms, a phenylcarbonyloxy group, or an alkylphenylsulfonyl group having 7 to 9 carbon atoms is represented. ]
［赤色分散染料］
［式中、Ｒ６は炭素数１〜６のアルキル基又はフェニル基を表す。
該アルキル基における水素原子は、水酸基、ハロゲン原子、炭素数１〜７のヒドロキシアルキル基、炭素数８〜１２のフェノキシカルボニルオキシアルキル基、炭素数７〜９のフェノキシアルキル基、炭素数７〜９のフェニルアルキル基及び炭素数３〜７のアルコキシカルボニルオキシアルキル基からなる群より選ばれる置換基で置換されていてもよい。また、該フェニル基における水素原子は、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、水酸基、ハロゲン原子、炭素数２〜４のアルキルカルボニルオキシ基、炭素数３〜７のアルコキシカルボニルアルコキシ基、炭素数２〜６のアルコキシアルキルアミノスルホニル基、炭素数３〜６のアルコキシカルボニルアルキル基、炭素数３〜６のアルキルカルボニルアルコキシ基、炭素数７〜９のフェニルアルコキシ基、炭素数３〜６のアルコキシカルボニルアルコキシ基及び炭素数１〜３のヒドロキシアルキルチオエーテル基からなる群より選ばれる置換基で置換されていてもよい。］
[Red disperse dye]
[Wherein R 6 represents an alkyl group having 1 to 6 carbon atoms or a phenyl group.
The hydrogen atom in the alkyl group is a hydroxyl group, a halogen atom, a hydroxyalkyl group having 1 to 7 carbon atoms, a phenoxycarbonyloxyalkyl group having 8 to 12 carbon atoms, a phenoxyalkyl group having 7 to 9 carbon atoms, or 7 to 9 carbon atoms. And may be substituted with a substituent selected from the group consisting of a phenylalkyl group and an alkoxycarbonyloxyalkyl group having 3 to 7 carbon atoms. Moreover, the hydrogen atom in this phenyl group is a C1-C3 alkyl group, a C1-C3 alkoxy group, a hydroxyl group, a halogen atom, a C2-C4 alkylcarbonyloxy group, a C3-C7 Alkoxycarbonylalkoxy group, C2-C6 alkoxyalkylaminosulfonyl group, C3-C6 alkoxycarbonylalkyl group, C3-C6 alkylcarbonylalkoxy group, C7-C9 phenylalkoxy group, carbon It may be substituted with a substituent selected from the group consisting of an alkoxycarbonylalkoxy group having 3 to 6 carbon atoms and a hydroxyalkylthioether group having 1 to 3 carbon atoms. ]
［式中、Ｒ７及びＲ８は、それぞれ独立に炭素数２〜４のアルキル基又はフェニル基を表す。
該アルキル基の水素原子は、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基、シアノ基、ハロゲン原子、水酸基、炭素数１〜４のヒドロキシアルコキシ基、炭素数２〜８のヒドロキシアルコキシアルコキシ基、炭素数３〜９のアルキルカルボニルオキシアルコキシ基、炭素数４〜１３のアルキルカルボニルオキシアルコキシアルコキシ基及び炭素数２〜８のアルコキシアルコキシ基からなる群より選ばれる置換基で置換されていてもよい。
また、該フェニル基の水素原子は、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基及び炭素数２〜８のアルコキシアルキル基からなる群より選ばれる置換基で置換されていてもよい。］
[Wherein, R 7 and R 8 each independently represents an alkyl group having 2 to 4 carbon atoms or a phenyl group.
The hydrogen atom of the alkyl group includes an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, a halogen atom, a hydroxyl group, a hydroxyalkoxy group having 1 to 4 carbon atoms, and 2 to 8 carbon atoms. Substituted with a substituent selected from the group consisting of a hydroxyalkoxyalkoxy group, an alkylcarbonyloxyalkoxy group having 3 to 9 carbon atoms, an alkylcarbonyloxyalkoxyalkoxy group having 4 to 13 carbon atoms and an alkoxyalkoxy group having 2 to 8 carbon atoms. It may be.
Further, the hydrogen atom of the phenyl group is substituted with a substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms and an alkoxyalkyl group having 2 to 8 carbon atoms. Also good. ]
［式中、Ｒ９及びＲ１０は、それぞれ独立に水素原子、ニトロ基、シアノ基、カルボキシ基、ハロゲン原子、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、炭素数６〜１０のアリール基、炭素数６〜１０のアリールオキシ基、炭素数２〜４のアルコキシカルボニル基、炭素数２〜４のアルキルカルボニル基、炭素数２〜４のアルキルカルボニルアミノ基、アミノカルボニル基、炭素数１〜３のアルキルスルホニル基、炭素数６〜１０のアリールスルホニル基又はアミノスルホニル基を表す。
Ｒ１１は、水素原子、炭素数１〜３のアルキル基、炭素数４〜９の直鎖状アルキル基、炭素数４〜９の分枝状アルキル基、炭素数１〜３のヒドロキシアルキル基、炭素数２〜６のアルコキシアルキル基、炭素数３〜７のアルコキシカルボニルアルキル基、炭素数３〜７のアルキルカルボニルオキシアルキル基、炭素数２〜４のシアノアルキル基、炭素数１〜３のアミノアルキル基、炭素数３〜９のＮ，Ｎ−ジアルキルアミノアルキル基、炭素数２〜６のアルキルアミノアルキル基、炭素数１〜３のハロゲノアルキル基、炭素数２〜４のカルボキシアルキル基、炭素数５〜７のモルホリノアルキル基、炭素数５〜７のシクロアルキル基、炭素数７〜１０のアラルキル基又は炭素数６〜１０のアリール基を表す。］
[Wherein R 9 and R 10 are each independently a hydrogen atom, a nitro group, a cyano group, a carboxy group, a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or 6 carbon atoms. C-10 aryl group, C6-C10 aryloxy group, C2-C4 alkoxycarbonyl group, C2-C4 alkylcarbonyl group, C2-C4 alkylcarbonylamino group, aminocarbonyl group Represents an alkylsulfonyl group having 1 to 3 carbon atoms, an arylsulfonyl group having 6 to 10 carbon atoms, or an aminosulfonyl group.
R 11 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a linear alkyl group having 4 to 9 carbon atoms, a branched alkyl group having 4 to 9 carbon atoms, a hydroxyalkyl group having 1 to 3 carbon atoms, C2-C6 alkoxyalkyl group, C3-C7 alkoxycarbonylalkyl group, C3-C7 alkylcarbonyloxyalkyl group, C2-C4 cyanoalkyl group, C1-C3 amino An alkyl group, an N, N-dialkylaminoalkyl group having 3 to 9 carbon atoms, an alkylaminoalkyl group having 2 to 6 carbon atoms, a halogenoalkyl group having 1 to 3 carbon atoms, a carboxyalkyl group having 2 to 4 carbon atoms, carbon A morpholinoalkyl group having 5 to 7 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms is represented. ]
上式（ＩＩＩ）〜（ＩＸ）で示される分散染料は、公知の化合物である。
本発明の黄色分散染料組成物は、疎水性繊維材料の染色若しくは捺染や、昇華転写型乾熱記録用途の色素等として有用である。具体的には、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、ポリアミドやポリカーボネート等の疎水性材料の着色に有用である。
本発明の黄色分散染料組成物は、特に疎水性繊維材料の染色又は捺染の用途に適している。
本発明の黄色分散染料組成物は、上式（Ｉ）及び（ＩＩ）で示される化合物をそれぞれ個別に製造した後、各化合物の混合物を得、これを分散染料化してもよい。また、複数の原料化合物を同じ反応容器中で同時に反応させて反応混合物を得、該混合物を直接分散染料化してもよい。
分散染料化は、製造により得られた分散染料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分散剤等の単独又は混合物を加えて、サンドミル中で湿式法により微粒化分散して得た液状品、或いは該液状品を乾燥して得たパウダー品を、それぞれ所定量配合してもよい。また、これらのパウダー品を、染色時に染浴中で配合してもよい。ポリエステル繊維等の疎水性繊維材料を染色する際には、本発明の黄色分散染料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調整剤や分散均染剤等を加えた後、繊維材料を浸漬後、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又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等のキャリヤーの存在下で、比較的低温、例えば水の沸騰状態で染色することもできる。さらに、染料の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、これを布に印捺後、スチーミング又は乾熱処理を行う。捺染はインクジェット方式で行ってもよい。
本発明の黄色分散染料組成物には、耐光堅牢度の優れた着色物を得る目的で、下記に示すベンゾトリアゾール系化合物やベンゾフェノン系化合物等の紫外線吸収剤を加えてもよい。
The disperse dyes represented by the above formulas (III) to (IX) are known compounds.
The yellow disperse dye composition of the present invention is useful as a dye for use in dyeing or printing of hydrophobic fiber materials, sublimation transfer type dry heat recording, and the like. Specifically, it is useful for coloring hydrophobic materials such as polyester, cationic dyeable polyester, diacetate, triacetate, polyamide and polycarbonate.
The yellow disperse dye composition of the present invention is particularly suitable for use in dyeing or printing hydrophobic fiber materials.
The yellow disperse dye composition of the present invention may be prepared by individually preparing the compounds represented by the above formulas (I) and (II), and then obtaining a mixture of the respective compounds to form a disperse dye. Alternatively, a plurality of raw material compounds may be reacted simultaneously in the same reaction vessel to obtain a reaction mixture, and the mixture may be directly converted into a disperse dye.
Disperse dyeing is a liquid obtained by adding a formalin condensate of naphthalene sulfonic acid or a lignin sulfonic acid dispersant alone or in mixture to the disperse dye obtained by production, and atomizing and dispersing by a wet method in a sand mill. A predetermined amount of each product or powder product obtained by drying the liquid product may be blended. Moreover, you may mix | blend these powder products in a dyeing bath at the time of dyeing | staining. When dyeing a hydrophobic fiber material such as polyester fiber, a pH adjusting agent or a dispersion leveling agent is added to the dyeing bath in which the yellow disperse dye composition of the present invention is dispersed in an aqueous medium, if necessary. After dipping, the fiber material is dyed at 105 ° C. or higher (preferably 110 to 140 ° C.) for 30 to 60 minutes under pressure. This dyeing time can be shortened or extended depending on the state of dyeing. It can also be dyed at a relatively low temperature, for example, in a boiling state of water, in the presence of a carrier such as o-phenylphenol or methylnaphthalene. Further, a dyeing method in which a dye dispersion liquid is padded on a cloth and then steaming or dry heat treatment at 100 ° C. or higher is also possible. In the case of printing, the dye dispersion is kneaded together with an appropriate paste, printed on a cloth, and then subjected to steaming or dry heat treatment. Textile printing may be performed by an ink jet method.
To the yellow disperse dye composition of the present invention, an ultraviolet absorber such as a benzotriazole compound or a benzophenone compound shown below may be added for the purpose of obtaining a colored product having excellent light fastness.
上記の紫外線吸収剤の使用量は、好ましくは、疎水性繊維材料等の被染色物の１００重量部当り、０．５〜５重量部の範囲である。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、ポリアミドやポリカーボネート等が挙げられる。またポリエステル繊維と他の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、羊毛や絹との混紡品又は交織品が挙げられる。
本発明の黄色分散染料組成物は、ポリエステル系の繊維材料が例えばポリエスル極細フィラメント糸、異形断面糸やＴｉＯ２等を含む艶けし加工糸のような各種加工糸や改質糸であっても、優れた均染性と再現性で耐光堅牢度の優れた着色物を得ることができる。また、本発明の黄色分散染料組成物は、染色時のターリングが少ない点においても優れる。さらに、得られた着色物は、高温で長時間光に曝される自動車内装材、例えば座席シート等としても使用可能である。
The amount of the ultraviolet absorber used is preferably in the range of 0.5 to 5 parts by weight per 100 parts by weight of the object to be dyed such as a hydrophobic fiber material. Examples of the hydrophobic fiber material include polyester, cationic dyeable polyester, diacetate, triacetate, polyamide and polycarbonate. Examples of the mixture of polyester fiber and other fibers include polyamide, diacetate, cationic dyeable polyester, cellulose fiber, a blend of wool and silk, or a cross-woven product.
In the yellow disperse dye composition of the present invention, even if the polyester fiber material is various processed yarns such as polyester ultrafine filament yarns, deformed cross-sectional yarns, glazed processed yarns containing TiO 2, and modified yarns, A colored product having excellent light fastness with excellent leveling and reproducibility can be obtained. In addition, the yellow disperse dye composition of the present invention is also excellent in that there is little turling during dyeing. Furthermore, the obtained colored product can be used as an automobile interior material that is exposed to light at a high temperature for a long time, such as a seat.
以下、実施例等により本発明を更に詳しく説明するが、本発明はこれらの例によって何ら限定されるものではない。なお、例中の部及び％は、各々重量部及び重量％を表わす。 EXAMPLES Hereinafter, although an Example etc. demonstrate this invention further in detail, this invention is not limited at all by these examples. In addition, the part and% in an example represent a weight part and weight%, respectively.
比較例１、比較例２及び実施例１〜５
下式（１）
で示される化合物３００ｇ、及び下式（２）
で示される化合物３００ｇを、それぞれ個別に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。上記の化合物（１）及び（２）を合計３０％、アニオン系分散剤を６５％、水分５％を含む分散染料組成物を得た。
Comparative Example 1, Comparative Example 2 and Examples 1-5
The following formula (1)
And 300 g of the compound represented by formula (2)
Each of the compounds represented by the formula (1) was individually atomized in 600 g of water together with 300 g of formalin condensate of sodium naphthalene sulfonate, and then 350 g of lignin sulfonic acid was added, followed by spray drying. A disperse dye composition containing 30% of the compounds (1) and (2), 65% of an anionic dispersant, and 5% of water was obtained.
上記の組成物を表１における例番号の各欄に記載の部数秤量し、秤量後の組成物を水２００部に分散させた。その後、酢酸と酢酸ナトリウムを添加してｐＨ５に調整して、染浴を作製した。
この染浴中に東レ（株）製のテトロントロピカル（ポリエステル布）１０部を浸した後、毎分１℃の割合で６０℃から１３０℃まで昇温した。次いで、１３０℃で６０分間染色した。得られた染色物を、カセイソーダ３部、ハイドロサルファイト３部、ベタイン型両性界面活性剤３部及び水３００部からなる処理液を用いて８５℃で１０分間還元洗浄処理を行った後、水洗及び乾燥して染色布の１〜７を得た。
得られた各染色布の表面濃度を分光光度計（マクベス社製のカラーアイ３０００型）により測定した。表面濃度は、クベルカ・ムンクの式により計算した[Ｋ／Ｓ]で表した（１９８２年３月２５日株式会社朝倉書店発行の「染色事典」の第９６頁を参照）。
分散染料化合物（１）のみを用いた場合の染着性に対する、本発明の黄色分散染料組成物の染着性改善効果を、以下の式により染着性改善指数（ＤＩ）として評価した。
The above composition was weighed in the number of parts described in each column of the example number in Table 1, and the weighed composition was dispersed in 200 parts of water. Thereafter, acetic acid and sodium acetate were added to adjust the pH to 5 to prepare a dye bath.
After 10 parts of Tetoron Tropical (polyester cloth) manufactured by Toray Industries, Inc. was immersed in this dye bath, the temperature was raised from 60 ° C. to 130 ° C. at a rate of 1 ° C. per minute. Subsequently, it dye | stained for 60 minutes at 130 degreeC. The obtained dyed product was subjected to a reduction washing treatment at 85 ° C. for 10 minutes using a treatment solution comprising 3 parts of caustic soda, 3 parts of hydrosulfite, 3 parts of a betaine amphoteric surfactant and 300 parts of water, and then washed with water. And dried to obtain dyed fabrics 1-7.
The surface concentration of each dyed cloth obtained was measured with a spectrophotometer (Color Eye Model 3000 manufactured by Macbeth). The surface concentration was expressed by [K / S] calculated by Kubelka-Munk formula (see page 96 of “Dyeing Dictionary” published on March 25, 1982 by Asakura Shoten).
The dyeing property improving effect of the yellow disperse dye composition of the present invention on the dyeing property when only the disperse dye compound (1) was used was evaluated as a dyeing property improvement index (DI) by the following formula.
染着性改善指数（ＤＩ）＝（染色布２〜７の各表面濃度［Ｋ／Ｓ］）／（染色布１の表面濃度［Ｋ／Ｓ］） Dyeing property improvement index (DI) = (each surface concentration [K / S] of dyed fabrics 2 to 7) / (surface concentration of dyed fabric 1 [K / S])
染着性改善指数（ＤＩ）に基づいて染着性の改善効果を以下のように分類した（下表１を参照）。
上記ＤＩが１．０１を超えれば、◎評価とした。また、ＤＩが０．９８〜１．０１の範囲であれば、○評価とした。そして、ＤＩが０．９０以上且つ０．９８未満であれば、×評価とした。
The effect of improving dyeing property was classified as follows based on the dyeing property improvement index (DI) (see Table 1 below).
If the DI exceeded 1.01, it was rated as ◎. Moreover, if DI was in the range of 0.98 to 1.01, it was rated as o. When DI was 0.90 or more and less than 0.98, x was evaluated.
実施例６〜１０
下式（３）
Examples 6-10
The following formula (3)
で示される化合物の３００ｇ、下式（４） 300 g of the compound represented by formula (4)
で示される化合物の３００ｇ、下式（５） 300 g of the compound represented by formula (5)
で示される化合物３００ｇ及び下式（６） 300 g of the compound represented by the formula (6)
で示される化合物３００ｇを、実施例１〜５と同様の方法により、それぞれ個別に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湿式解膠した。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（３）〜（６）のそれぞれの３０％、アニオン系分散剤６５％及び水分５％から成る分散染料組成物を得た。 In the same manner as in Examples 1 to 5, 300 g of the compound represented by the formula was individually wet-peptized with a sand mill in 600 g of water together with 300 g of formalin condensate of sodium naphthalenesulfonate. Next, 350 g of lignin sulfonic acid was added, followed by spray drying. As a dried product, a disperse dye composition comprising 30% of each of the compounds (3) to (6), 65% of an anionic dispersant and 5% of water was obtained.
上式（１）〜（６）の化合物を用いて、下表２における例番号６〜１０の各欄に記載の部数秤量し、秤量後の各色組成物を水２００部に分散させた。その後、酢酸と酢酸ナトリウムを添加してｐＨ５に調整して、染浴を作製した。
この染浴中に東レ（株）製のテトロントロピカル（ポリエステル布）１０００部を浸した後、毎分１℃の割合で６０℃から１３０℃まで昇温した。次いで、１３０℃で６０分間染色した。得られた染色物を、カセイソーダ３０部、ハイドロサルファイト３０部、ベタイン型両性界面活性剤３０部及び水３００００部からなる処理液を用いて８５℃で１０分間還元洗浄処理を行った後、水洗及び乾燥して表２記載の色相の均一な染色物を再現性良く得た。
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 ０８０４−１９６５変褪色用グレースケールにて判定した。表２記載のとおり、耐光堅牢度はいずれも４級以上と良好であった。
Using the compounds of the above formulas (1) to (6), the number of parts described in each column of Example Nos. 6 to 10 in Table 2 below was weighed, and each color composition after weighing was dispersed in 200 parts of water. Thereafter, acetic acid and sodium acetate were added to adjust the pH to 5 to prepare a dye bath.
After immersing 1000 parts of Tetoron Tropical (polyester cloth) manufactured by Toray Industries, Inc. in this dye bath, the temperature was raised from 60 ° C. to 130 ° C. at a rate of 1 ° C. per minute. Subsequently, it dye | stained for 60 minutes at 130 degreeC. The obtained dyed product was subjected to a reduction washing treatment at 85 ° C. for 10 minutes using a treatment liquid comprising 30 parts of caustic soda, 30 parts of hydrosulfite, 30 parts of a betaine amphoteric surfactant and 30000 parts of water, and then washed with water. And dried to obtain a dyed product having a uniform hue described in Table 2 with good reproducibility.
Light fastness is based on JIS L 0804-1965 gray scale for discoloration after lining urethane foam on dyed fabric, irradiating at 83 ° C for 600 hours in carbon arc fade meter (Suga Test Machine Long Life Type). Judged. As shown in Table 2, the fastness to light was as good as grade 4 or higher.
実施例１１
式（１）で示される化合物７２部と、式（２）で示される化合物８部と、下式（７）で示される化合物２０部を、実施例１と同様に湿式解膠後、リグニンスルホン酸３５部を加え、噴霧乾燥後、３０％の染料分を含む黄色分散染料組成物を得た。
Example 11
72 parts of the compound represented by the formula (1), 8 parts of the compound represented by the formula (2), and 20 parts of the compound represented by the following formula (7) were subjected to wet peptization in the same manner as in Example 1, and then lignin sulfone. 35 parts of acid was added, and after spray drying, a yellow disperse dye composition containing 30% of the dye content was obtained.
また、式（３）で示される化合物２５部と式（４）で示される化合物７５部を実施例１と同様にして湿式解膠後、リグニンスルホン酸３５部を加え、次いで噴霧乾燥して３０％の染料分を含む青色分散染料組成物を得た。
さらに、式（５）で示される化合物１０部と式（６）で示される化合物９０部を実施例１と同様に湿式解膠後、リグニンスルホン酸３５部を加え、次いで噴霧乾燥して３０％の染料分を含む赤色分散染料組成物を得た。
上記の黄色分散染料組成物１．５ｇと青色分散染料組成物１．４ｇ及び赤色分散染料組成物２．５ｇを染浴中に配合し、水１０００ｍｌ中に分散させた後、酢酸と酢酸ナトリウムを添加してｐＨを５に調整して染浴を作製した。
染浴には、下式（８）で示される紫外線吸収剤の分散液［紫外線吸収剤４０％、アニオン系分散剤２０％及び水４０％から成る混合物］を２ｇ添加した。
Further, 25 parts of the compound represented by the formula (3) and 75 parts of the compound represented by the formula (4) were wet peptized in the same manner as in Example 1 and 35 parts of lignin sulfonic acid was added, followed by spray drying. A blue disperse dye composition containing% dye was obtained.
Further, 10 parts of the compound represented by the formula (5) and 90 parts of the compound represented by the formula (6) were wet peptized in the same manner as in Example 1, 35 parts of lignin sulfonic acid was added, and then spray-dried to obtain 30%. A red disperse dye composition containing the dye component was obtained.
After blending 1.5 g of the yellow disperse dye composition, 1.4 g of the blue disperse dye composition and 2.5 g of the red disperse dye composition in a dye bath and dispersing in 1000 ml of water, acetic acid and sodium acetate are added. A dye bath was prepared by adding to adjust the pH to 5.
In the dye bath, 2 g of a dispersion of an ultraviolet absorber represented by the following formula (8) [a mixture composed of 40% ultraviolet absorber, 20% anionic dispersant and 40% water] was added.
上記の染浴に東レ（株）製のテトロントロピカル［ポリエステル］１００ｇを浸し、実施例２と同様に染色した。得られた染色物はこげ茶色に均一に再現性良く染色された。上述し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照射後（検出波長３４０ｎｍ）、ＪＩＳ Ｌ０８０４−１９６５変褪色用グレースケールで判定した。この染色布の耐光堅牢度は４級以上であった。 100 g of Tetoron tropical [polyester] manufactured by Toray Industries, Inc. was immersed in the above dye bath, and dyed in the same manner as in Example 2. The resulting dyed product was uniformly dyed dark brown with good reproducibility. Each of the above-mentioned dyed cloths is lined with urethane foam, and an ultraviolet cut filter that blocks light of 310 nm or less is attached 1 cm from the surface of the sample after 750 kJ irradiation with a xenon fade meter (black panel temperature 89 ° C.) ( The detection wavelength was 340 nm, and the gray scale for JIS L0804-1965 discoloration was used. The light fastness of this dyed fabric was 4 or higher.
実施例１２〜１６
１）実施例１２
実施例１１と同様にして、上記の化合物（１）及び（２）と、下記化合物（９）〜（１２）のそれぞれとを湿式解膠後［重量比は表３に記載］、リグニンスルホン酸３５部を加えて噴霧乾燥後、化合物（９）〜（１２）のそれぞれを含む黄色分散染料組成物を得た（染料分含量３０％）。
２）実施例１３〜１６
実施例１２において使用した黄色分散染料組成物の代りに、上記で得た黄色分散染料組成物を用いて染色を行って、こげ茶色に均一に染色されたポリエステル染色布を得た。
化合物（９）〜（１２）のいずれにおいても、再現性良く染色布が得られた。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３４０ｎｍ）、ＪＩＳ Ｌ０８０４−１９６５変褪色用グレースケールで判定した。実施例１２〜１５で得た染色布の耐光堅牢度はいずれも４級以上であり、良好であった（下表３を参照）。
Examples 12-16
1) Example 12
In the same manner as in Example 11, the above compounds (1) and (2) and each of the following compounds (9) to (12) were subjected to wet peptization [weight ratio is listed in Table 3], lignin sulfonic acid After adding 35 parts and spray-drying, a yellow disperse dye composition containing each of the compounds (9) to (12) was obtained (dye content 30%).
2) Examples 13-16
Instead of the yellow disperse dye composition used in Example 12, dyeing was performed using the yellow disperse dye composition obtained above to obtain a polyester dyed cloth uniformly dyed in dark brown.
In any of the compounds (9) to (12), a dyed fabric was obtained with good reproducibility. Each dyed cloth is lined with urethane foam, and an ultraviolet cut filter that blocks light of 310 nm or less is attached 1 cm from the surface of the sample, and irradiated with 750 kJ with a xenon fade meter (black panel temperature 89 ° C.) (detection wavelength 340 nm). ), And a gray scale for JIS L0804-1965 discoloration color. The light fastnesses of the dyed fabrics obtained in Examples 12 to 15 were all grades 4 and above and were good (see Table 3 below).
本発明の分散染料組成物は、ポリエステル等の疎水性繊維材料を着色する際に有用である。また、本発明の分散染料組成物は、昇華転写型乾熱記録用色素としても有用である。
The disperse dye composition of the present invention is useful when coloring hydrophobic fiber materials such as polyester. The disperse dye composition of the present invention is also useful as a dye for sublimation transfer type dry heat recording.
Claims (5)
［式中、Ｒ１は炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基又はフェニル基を表す。該フェニル基における水素原子は、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ハロゲン原子、水酸基、炭素数２〜４のアルキルカルボニルオキシ基、炭素数３〜７のアルコキシカルボニルアルコキシ基及び炭素数２〜６のアルコキシアルキルアミノスルホニル基からなる群より選ばれる置換基で置換されていてもよい。］
A yellow disperse dye composition comprising a disperse dye represented by the following formula (I) and a disperse dye represented by the following formula (II).
[Wherein, R 1 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a phenyl group. The hydrogen atom in the phenyl group is an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom, a hydroxyl group, an alkylcarbonyloxy group having 2 to 4 carbon atoms, or an alkoxycarbonyl having 3 to 7 carbon atoms. It may be substituted with a substituent selected from the group consisting of an alkoxy group and an alkoxyalkylaminosulfonyl group having 2 to 6 carbon atoms. ]
The blue disperse dye represented by the following formula (3) or the following formula (4) and / or the red disperse dye represented by the following formula (5) or the following formula (6) : A disperse dye composition for three primary colors, comprising a yellow disperse dye composition .
A method for coloring a hydrophobic fiber material, wherein the disperse dye composition according to claim 1 is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004243417A JP4470646B2 (en) | 2004-08-24 | 2004-08-24 | Disperse dye composition and method for coloring hydrophobic material using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004243417A JP4470646B2 (en) | 2004-08-24 | 2004-08-24 | Disperse dye composition and method for coloring hydrophobic material using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006057065A JP2006057065A (en) | 2006-03-02 |
| JP4470646B2 true JP4470646B2 (en) | 2010-06-02 |
Family
ID=36104803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004243417A Expired - Fee Related JP4470646B2 (en) | 2004-08-24 | 2004-08-24 | Disperse dye composition and method for coloring hydrophobic material using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4470646B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011126273A (en) * | 2009-11-18 | 2011-06-30 | Pilot Ink Co Ltd | Discoloring laminate |
| KR101273457B1 (en) * | 2011-05-06 | 2013-06-11 | (주)경인양행 | Disperse Dyes Composites and Methods of Dyeing Fiber Using the Same |
| CN107043554A (en) * | 2016-08-31 | 2017-08-15 | 浙江龙盛集团股份有限公司 | A kind of red disperse dyes composition and dye preparations |
| CN109371711A (en) * | 2018-08-21 | 2019-02-22 | 浙江弘盛纺织科技有限公司 | A kind of dyeing and finishing technology of resistance to high PVC staining color fastness terylene home-textile |
| KR20220141311A (en) | 2020-02-14 | 2022-10-19 | 다이쿄 케미칼 컴퍼니, 리미티드 | Simultaneous dyeing and flame-retardant processing method for polyester-based textiles |
-
2004
- 2004-08-24 JP JP2004243417A patent/JP4470646B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006057065A (en) | 2006-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5048479B2 (en) | Disperse dye, disperse dye composition, ink for ink-jet printing, dyeing method and dyed material using these | |
| JP5851417B2 (en) | Disperse dye and method for dyeing hydrophobic fiber material using the same | |
| KR20070024516A (en) | Disperse dyes for poly(lactic acid) based fibers | |
| EP1879964B1 (en) | Dye mixtures | |
| EP1644447B1 (en) | Disperse dye mixtures which have a high degree of light fastness | |
| JPH07331104A (en) | Dye composition and method for coloring hydrophobic material using the same | |
| JP4470646B2 (en) | Disperse dye composition and method for coloring hydrophobic material using the same | |
| JPH09176509A (en) | Colored composition high in light resistance and coloring of hydrophobic material using the same | |
| JPH0834933A (en) | Dye composition and method for coloring hydrophobic material | |
| JPWO2012073696A1 (en) | Disperse dye and method for dyeing hydrophobic fiber material using the same | |
| US4690686A (en) | Light-fast yellow disperse dye composition for polyester | |
| JP2006193574A (en) | Disperse dye composition, and application to hydrophobic fiber material | |
| JPH04164969A (en) | Disperse dye composition and method of dyeing hydrophobic fiber | |
| JPH024625B2 (en) | ||
| JP5773520B2 (en) | Disperse dye composition and method for dyeing hydrophobic fiber material using the same | |
| KR20220111622A (en) | Disperse black dye mixture, preparation method and use thereof | |
| JPH04173875A (en) | Disperse dye composition and method for dyeing hydrophobic fiber | |
| JP4483476B2 (en) | Disperse dye composition | |
| JP3173193B2 (en) | Highly light-resistant coloring composition and method for coloring hydrophobic material using the same | |
| JPH04122779A (en) | Disperse dye composition and method for dyeing hydrophobic fiber therewith | |
| JP2820787B2 (en) | Dyeing method for disperse dye composition and hydrophobic fiber | |
| JP3316925B2 (en) | 3-phenyl-7- [4- (tetrahydrofurfuryloxy) phenyl] -1,5-dioxa-s-indacene-2,6-dione | |
| EP3607002A1 (en) | Colorant mixtures | |
| JP5917517B2 (en) | Disperse dye composition and method for dyeing hydrophobic fiber material using the same | |
| JPS63213569A (en) | Disperse dye composition and dyeing of hydrophobic fiber using said dye |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20070405 |
|
| RD05 | Notification of revocation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7425 Effective date: 20080130 |
|
| RD05 | Notification of revocation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7425 Effective date: 20080513 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091208 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100118 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100209 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100222 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130312 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130312 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130312 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140312 Year of fee payment: 4 |
|
| LAPS | Cancellation because of no payment of annual fees |