WO2014061568A1 - 酸性染料組成物及びそれを用いる染色法 - Google Patents
酸性染料組成物及びそれを用いる染色法 Download PDFInfo
- Publication number
- WO2014061568A1 WO2014061568A1 PCT/JP2013/077699 JP2013077699W WO2014061568A1 WO 2014061568 A1 WO2014061568 A1 WO 2014061568A1 JP 2013077699 W JP2013077699 W JP 2013077699W WO 2014061568 A1 WO2014061568 A1 WO 2014061568A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dye
- formula
- acid dye
- acid
- nylon
- Prior art date
Links
Classifications
-
- 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide 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
- 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
-
- 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
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/6008—Natural or regenerated cellulose using acid dyes
Definitions
- the present invention relates to an acid dye composition and a dyeing method using the same. More specifically, a dye composition containing two specific red acid dyes, a mixture of the red acid dye, a dye composition containing a yellow acid dye and / or a blue acid dye, and the same The present invention relates to a dyeing method for polyamide fibers and the like.
- yellow acid dyes, red acid dyes, and blue acid dyes have the same dyeability, and are excellent in fastness and dyeability.
- a high-performance acidic dye composition that is uniform and has good reproducibility, and a dyeing method using the same.
- the present inventors combine a specific red acid dye, a mixture of the red acid dye, a specific yellow acid dye and / or a specific blue acid dye. By combining them, a dye composition having not only strong fastness of each color but also fastness with good balance among the three primary colors and uniform dyeing characteristics at the time of dyeing was found, and the present invention was completed.
- the present invention relates to the following 1) to 8).
- a dye composition comprising a red acidic dye mixture (B) comprising a red acidic dye represented by formula (2) and a red acidic dye represented by formula (3).
- the red acid dye represented by the formula (2) is 60 to 80% by weight, and the red acid dye represented by the formula (3) is 20 to 40% by weight.
- a dye composition comprising a blue acid dye mixture (C) comprising an acid dye.
- the blue acid dye represented by the formula (4) is 70 to 90% by weight, and the blue acid dye represented by the formula (5) is 10 to 30% by weight. 3) The dye composition as described.
- the blue acid dye represented by the formula (4) is 30 to 70% by weight
- the blue acid dye represented by the formula (5) is 10 to 50% by weight
- the dye composition according to 5) above, wherein the blue acid dye represented by 6) is 20 to 60% by weight.
- Dye composition containing a mixture (B) of two specific red acid dyes of the present invention a dye composition containing a red acid dye mixture (B) and a specific yellow acid dye (A), red A dye composition containing a base acid dye mixture (B) and a specific blue acid dye mixture (C), and a red acid dye mixture (B), a yellow acid dye (A) and a blue acid dye mixture (C ) Is high in various dyeing performances, and dyed products of polyamide fibers or cellulose-containing polyamide fibers using the dye compositions are particularly excellent in light fastness and dyed feet.
- the dye composition of the present invention contains a red acidic dye mixture (B) composed of a red acidic dye represented by the formula (2) and a red acidic dye represented by the formula (3).
- each dye is described in a free form, but may be a salt, and the salt is also included in the present invention.
- alkali metal salts such as lithium, sodium, potassium, etc. are mentioned, for example.
- the compound represented by the formula (2) is C.I. I. Acid Red 260, which can be produced by a method known in the literature or an application thereof, but a commercially available compound may be used.
- the compound represented by the formula (3) is C.I. I. Acid Red 299, which can be produced by a method known in the literature or an application thereof, but a commercially available compound may be used.
- the red acid dye represented by the formula (2) is preferably about 60 to 80% by weight, and the red acid dye represented by the formula (3) is preferably about 20 to 40% by weight.
- the dye composition of the present invention includes a red acidic dye mixture (B), a yellow acidic dye (A) represented by the formula (1) and / or a blue acidic dye represented by the formula (4) and A composition containing a blue acid dye mixture (C) composed of a blue acid dye represented by the formula (5) is also included.
- the compound represented by the formula (1) is C.I. I. Acid Orange 67, which can be produced by a method known in the literature or an application thereof, but a commercially available compound may be used.
- the compound represented by the formula (4) is C.I. I. Acid Blue 140, which can be produced by a method known in the literature or an application thereof, but a commercially available compound may be used.
- the compound represented by the formula (5) is C.I. I. Acid Blue 260, which can be produced by a method known in the literature or an application thereof, but a commercially available compound may be used.
- the blue acid dye represented by the formula (4) is preferably about 70 to 90% by weight, and the blue acid dye represented by the formula (5) is preferably about 10 to 30% by weight.
- the blue acid dye mixture (C) used in the present invention preferably further contains a blue acid dye represented by the formula (6).
- the compound represented by formula (6) is C.I. I. Acid Blue 138, which can be produced by a method known in the literature or an application thereof, but a commercially available compound may be used.
- the blue acid dye represented by the formula (4) is 30 in the blue acid dye mixture (C). It is preferable that the blue acid dye represented by the formula (5) is about 10 to 50% by weight, and the blue acid dye represented by the formula (6) is about 20 to 60% by weight.
- the dye composition of the present invention may contain a solvent such as water and an additive such as dextrin.
- a solvent such as water
- an additive such as dextrin.
- other acid dyes or dyes other than acid dyes may be mixed and used in order to adjust the color or to adjust fastness, dyeing characteristics, and the like.
- other acid dyes, other dyes and dyeing agents can be added and used at the time of dyeing.
- the maximum content of other dyes is about 10% or less.
- the fibers that can be dyed by the method of the present invention are not particularly limited, but polyamide fibers or cellulose-containing polyamide fibers are preferred.
- the polyamide fibers include synthetic polyamide fibers such as nylon, and natural polyamide fibers such as animal hair such as wool.
- Examples of the cellulose-containing polyamide fiber include a blend of natural or synthetic polyamide fiber and cellulose fiber such as cotton.
- the processing forms include loose hair, yarn, woven fabric, knitted fabric and the like.
- the fiber is immersed in an aqueous medium of the acid dye composition, and the temperature is about 110 to 1.1 atm. What is necessary is just to process for 30 minutes-1 hour at -100 degreeC. Thereafter, it is washed with water and, if necessary, dried in hot water and dried to obtain a dyed product.
- the present invention includes the dyeing method and fibers dyed by the dyeing method.
- the dye composition of the present invention may be produced by mixing each acid dye and then adding water or the like, or may be produced by mixing each acid dye after preparation.
- Red acid dyes (formula (2) dye (Acid Red 260) 0.138% ow Nylon (vs. nylon fiber weight), formula (3) dye (acid red 299) 0.057% ow Nylon 1000 parts of a dye bath were prepared by adding water adjusted to pH 4 to 6 with ammonium sulfate (5% ow Nylon (weight of nylon fibers)) to (weight of nylon fibers). After 50 parts of nylon fiber (nylon white cloth) was immersed and dyed at 100 ° C. for 30 minutes, washed with water and dried to obtain a red dyed product. The obtained dyed products were tested for light fastness, wet fastness, covering property, dyed foot, and cotton stain resistance. The results are shown in Table 1.
- Nylon fiber (nylon white cloth) that has been partially heat-treated (treated at 200 ° C for 30 seconds) is dyed in a dye bath at 100 ° C for 30 minutes, and then the heat-untreated and heat-treated portions are JIS L-0804 gray for discoloration Judged by scale. The results are shown in the table.
- Nylon fiber nylon white cloth
- was dyed at 100 ° C. for 30 minutes in a dye bath then washed with hot water at 95 ° C. for 15 minutes, and before and after washing with hot water, the gray scale for color change of JIS L-0804 was judged. The results are shown in the table.
- the wet fastness test includes the following two test methods, both of which were performed here, and the result of combining the results was defined as wet fastness.
- [Washing fastness test method] Nylon white cloth and cotton white cloth were attached to the dyed product, and the test cloth was treated in a JIS synthetic detergent (No. 3) 4 g / L washing water bath at 50 ° C. for 30 minutes, then washed with pure water and naturally dried. The contamination status of the attached white cloth was determined using the JIS L-0805 contamination gray scale, and the results are shown in the table.
- Nylon white cloth and cotton white cloth are attached to the dyeing, and the test cloth is adjusted to pH 8 with L-histidine hydrochloride 0.5 g / L, sodium chloride 5.0 g / L, disodium phosphate 5.0 g / L and sodium hydroxide. Then, the test cloth was sandwiched between plastic plates, pressed with a weight of 4.5 kg, treated with a dryer at 37 ° C. for 4 hours, and then naturally dried. The contamination status of the attached white cloth was determined using the JIS L-0805 contamination gray scale, and the results are shown in the table.
- the dyed product using the dye composition containing the red acidic dye mixture of the present invention is dyed in comparison with the dyed product using the dye composition containing the single red acid dye. Are also excellent in overall dye performance.
- Example 2 Yellow acid dye composition (formula (1) dye (Acid Orange 67) 0.162% ow Nylon (weight of nylon fiber)) and red acid dye composition (formula (2) dye 0.033% ow Nylon (weight of nylon fiber), formula (3) dye 0.014% ow Nylon (weight of nylon fiber)) and blue acid dye composition (formula (4) dye 0.098% ow Nylon (weight of nylon fiber), formula (5) dye 0.027% ow Nylon (weight of nylon fiber)), Kayaku Buffer P-7 (1 g / L), mirabilite (30 g / L) 1000 parts of a dye bath were prepared by adding water adjusted to pH 7 by L). 50 parts of nylon fiber (nylon white cloth) was immersed, dyed at 100 ° C.
- Example 3 Yellow acid dye composition (formula (1) dye (Acid Orange 67) 0.043% ow Nylon (weight of nylon fiber)) and red acid dye composition (formula (2) dye 0.017% ow Nylon (weight of nylon fiber), formula (3) dye 0.007% ow Nylon (weight of nylon fiber)) and blue acid dye composition (formula (4) dye 0.034% ow Nylon (weight to nylon fiber), formula (5) dye 0.019% ow Nylon (weight to nylon fiber), formula (6) dye 0.032% ow Nylon (weight to nylon) To the fiber weight)), water adjusted to pH 7 with Kayaku Buffer P-7 (1 g / L), Newbon TS-400 (0.3% Occasionallyw Nylon (weight of nylon fiber)) was added, and the dyeing bath 1000 Part It was prepared.
- nylon fibers nylon white cloth
- Each test of light fastness, wet fastness, and dyed foot was performed on the resulting dyed product, and the results are shown in Table 3.
- dyeing was performed under the dyeing conditions described in the above test method.
- Yellow acid dye composition (formula (1) dye (Acid Orange 67) 0.059% ow Nylon (weight of nylon fiber)) and red acid dye composition (formula (2) dye 0.022% ow Nylon (weight of nylon fiber), formula (3) dye 0.009% ow Nylon (weight of nylon fiber)) and blue acid dye composition (formula (4) dye 0.048% ow Nylon (weight of nylon fiber), formula (5) dye 0.026% ow Nylon (weight of nylon fiber), formula (6) dye 0.044% ow Nylon (weight of nylon) Fiber weight)), and adjusted to pH 7 with Kayaku Buffer P-7 (1 g / L), mirabilite (28 g / L), Newbon TS-400 (0.5% Maschinenw Nylon (vs.
- nylon fiber weight (nylon white cloth)) Water It added to prepare the 1,000 parts of dye bath. 50 parts of nylon fibers (nylon white cloth) were immersed and dyed at 100 ° C. for 60 minutes, then washed with water and dried to obtain a gray dyed product. Each test of light fastness, wet fastness, and dyed foot was performed on the resulting dyed product, and the results are shown in Table 3. In the dyed foot test, 50 parts of nylon fiber (nylon white cloth) is immersed, the temperature is raised from 30 ° C.
- the dyed product using the red acid dye mixture, the yellow acid dye composition, and the two blue acid dye mixtures of the present invention is a comparative example.
- a dyed product using a known dye composition containing a red acid dye, a yellow acid dye, and a blue acid dye it is superior in light fastness and wet fastness, and has dyed feet. And excellent in various dye performances.
- dyeing products using the red acid dye mixture, the yellow acid dye composition, and the three blue acid dye mixtures of the present invention are particularly resistant to light fastness. It has excellent wet fastness and has dyed feet.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201380054413.1A CN104736644B (zh) | 2012-10-19 | 2013-10-11 | 酸性染料组合物及使用其的染色法 |
KR1020157008736A KR101871556B1 (ko) | 2012-10-19 | 2013-10-11 | 산성 염료 조성물 및 그것을 이용하는 염색법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012231694A JP5975521B2 (ja) | 2012-10-19 | 2012-10-19 | 酸性染料組成物及びそれを用いる染色法 |
JP2012-231694 | 2012-10-19 |
Publications (1)
Publication Number | Publication Date |
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WO2014061568A1 true WO2014061568A1 (ja) | 2014-04-24 |
Family
ID=50488134
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2013/077699 WO2014061568A1 (ja) | 2012-10-19 | 2013-10-11 | 酸性染料組成物及びそれを用いる染色法 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP5975521B2 (ko) |
KR (1) | KR101871556B1 (ko) |
CN (1) | CN104736644B (ko) |
TW (1) | TWI619773B (ko) |
WO (1) | WO2014061568A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114410125A (zh) * | 2022-01-26 | 2022-04-29 | 杭州迈染新材料有限公司 | 一种酸性黑色染料组合物、酸性染料及其应用 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI659138B (zh) * | 2017-10-25 | 2019-05-11 | Everlight Chemical Industrial Corporation | 酸性染料組成物及其於染尼龍織物上的用途 |
CN109206942A (zh) * | 2018-09-05 | 2019-01-15 | 杭州下沙恒升化工有限公司 | 一种红色酸性染料组合物及其染色应用 |
CN110128848B (zh) * | 2019-05-18 | 2021-01-01 | 上海雅运新材料有限公司 | 一种红色酸性染料组合物及其在纤维上的染色应用 |
CN111548647B (zh) * | 2020-05-14 | 2022-02-25 | 上海安诺其集团股份有限公司 | 一种红色染料及其制备方法及其应用 |
Citations (6)
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---|---|---|---|---|
JPH06240586A (ja) * | 1992-09-30 | 1994-08-30 | Ciba Geigy Ag | 染料混合物による天然又は合成ポリアミド繊維材料の染色方法 |
JPH0790191A (ja) * | 1993-09-24 | 1995-04-04 | Taoka Chem Co Ltd | 赤色染料組成物、それを用いる染色法及びその染色物 |
JPH07179781A (ja) * | 1993-12-22 | 1995-07-18 | Taoka Chem Co Ltd | 赤色染料組成物、それを用いる染色法及びその染色物 |
JPH08239591A (ja) * | 1995-02-10 | 1996-09-17 | Ciba Geigy Ag | アゾ染料混合物及びその用途 |
JP2000080575A (ja) * | 1998-09-03 | 2000-03-21 | Toray Ind Inc | 芯鞘型複合繊維の染色方法 |
JP2004515657A (ja) * | 2000-12-05 | 2004-05-27 | クラリアント インターナショナル リミティド | 三原色染色法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JP3290486B2 (ja) | 1992-12-14 | 2002-06-10 | 田岡化学工業株式会社 | ポリアミド繊維用染料組成物、その染色法及びその染色物 |
JP3299015B2 (ja) | 1993-09-24 | 2002-07-08 | 田岡化学工業株式会社 | 青色染料組成物、それを用いる染色法及びその染色物 |
JPH0823959A (ja) * | 1994-07-12 | 1996-01-30 | Idemitsu Kosan Co Ltd | 細菌検出器具 |
JPH0894826A (ja) * | 1994-09-21 | 1996-04-12 | Nippon Kayaku Co Ltd | インク組成物及びそれを用いて作製するカラーフィルター |
WO2000003082A1 (de) * | 1998-07-08 | 2000-01-20 | Ciba Specialty Chemicals Holding Inc. | Verfahren zum bedrucken von textilen fasermaterialien nach dem tintenstrahldruck-verfahren |
AU5742999A (en) * | 1998-09-10 | 2000-04-03 | Ciba Specialty Chemicals Holding Inc. | Method for dyeing fibrous materials containing cellulose |
EP2251325A1 (en) * | 2009-05-14 | 2010-11-17 | Clariant International Ltd. | Bisazo compounds |
-
2012
- 2012-10-19 JP JP2012231694A patent/JP5975521B2/ja not_active Expired - Fee Related
-
2013
- 2013-10-08 TW TW102136352A patent/TWI619773B/zh not_active IP Right Cessation
- 2013-10-11 CN CN201380054413.1A patent/CN104736644B/zh not_active Expired - Fee Related
- 2013-10-11 WO PCT/JP2013/077699 patent/WO2014061568A1/ja active Application Filing
- 2013-10-11 KR KR1020157008736A patent/KR101871556B1/ko active IP Right Grant
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06240586A (ja) * | 1992-09-30 | 1994-08-30 | Ciba Geigy Ag | 染料混合物による天然又は合成ポリアミド繊維材料の染色方法 |
JPH0790191A (ja) * | 1993-09-24 | 1995-04-04 | Taoka Chem Co Ltd | 赤色染料組成物、それを用いる染色法及びその染色物 |
JPH07179781A (ja) * | 1993-12-22 | 1995-07-18 | Taoka Chem Co Ltd | 赤色染料組成物、それを用いる染色法及びその染色物 |
JPH08239591A (ja) * | 1995-02-10 | 1996-09-17 | Ciba Geigy Ag | アゾ染料混合物及びその用途 |
JP2000080575A (ja) * | 1998-09-03 | 2000-03-21 | Toray Ind Inc | 芯鞘型複合繊維の染色方法 |
JP2004515657A (ja) * | 2000-12-05 | 2004-05-27 | クラリアント インターナショナル リミティド | 三原色染色法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114410125A (zh) * | 2022-01-26 | 2022-04-29 | 杭州迈染新材料有限公司 | 一种酸性黑色染料组合物、酸性染料及其应用 |
Also Published As
Publication number | Publication date |
---|---|
CN104736644B (zh) | 2016-07-06 |
KR101871556B1 (ko) | 2018-06-27 |
KR20150076154A (ko) | 2015-07-06 |
JP5975521B2 (ja) | 2016-08-23 |
CN104736644A (zh) | 2015-06-24 |
TW201439225A (zh) | 2014-10-16 |
TWI619773B (zh) | 2018-04-01 |
JP2014084329A (ja) | 2014-05-12 |
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