KR101075939B1 - Reactive dye composition and method of dyeing with the same - Google Patents
Reactive dye composition and method of dyeing with the same Download PDFInfo
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- KR101075939B1 KR101075939B1 KR1020057014365A KR20057014365A KR101075939B1 KR 101075939 B1 KR101075939 B1 KR 101075939B1 KR 1020057014365 A KR1020057014365 A KR 1020057014365A KR 20057014365 A KR20057014365 A KR 20057014365A KR 101075939 B1 KR101075939 B1 KR 101075939B1
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- 0 C*(c1c(**)c2cccc(*)c2cc1)c(c(O)c(c(C)c(*1=C(C*c2c(*(C)(*)I)ccc(*C(*=C(CCc3cccc(N=O)c3)*=*N)=C)c2)C1)c([N+](*)[O-])c1)c1c1)c1N Chemical compound C*(c1c(**)c2cccc(*)c2cc1)c(c(O)c(c(C)c(*1=C(C*c2c(*(C)(*)I)ccc(*C(*=C(CCc3cccc(N=O)c3)*=*N)=C)c2)C1)c([N+](*)[O-])c1)c1c1)c1N 0.000 description 3
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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
- C09B67/0042—Mixtures containing two reactive dyes one of them being an azo dye
- C09B67/0045—Mixtures containing two reactive dyes one of them being an azo dye both having the reactive group not directly attached to a heterocyclic system
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Abstract
Reactive containing a blue reactive dye represented by the following formula (A) and a blue reactive dye represented by the formula (1) for dyeing the cellulose fibers with a balanced affinity, reactivity as well as reproducibility, uniformity and fastness Dye compositions and dyeing methods using the same are provided.
In formula (A), R represents a hydrogen atom or the like, m 1 represents an integer of 0 to 2 in formula (1), R 1 and R 2 represent a hydrogen atom, an alkyl group, and the like, X 1 is halogen represents an atom, Y 1 is -SO 2 CH = CH 2 And the like.
Cellulose fiber, homogeneous, reproducible, blue reactive dye, red reactive dye, yellow reactive dye
Description
The present invention relates to a reactive dye composition suitable for dyeing cellulose fibers and cellulose fiber-containing fiber materials and a dyeing method using the same.
Reactive dyes are widely used for dyeing cellulose fibers such as cotton and rayon. In dyeing cellulose fiber materials using a reactive dye, it is known that a method of dyeing by combining yellow, red and blue reactive dyes as the three primary colors and blending them in various ratios is known.
However, when the affinity, reactivity, dyeing speed, and temperature dependence of each dye to be applied as the dye for the three primary colors are respectively different, problems such as dyeability such as dye staining during dyeing and dye reproducibility resulting in color difference between dye lots Can occur. Regarding the leveling and dye reproducibility In recent years, various types and types of textile materials are diversified, automation of dyeing factories, and the simplification of the work for shortening the dyeing time are required. Therefore, there is a strong demand for reactive dyes having good leveling and dyeing reproducibility. It is becoming. In order to solve such a problem, various examinations have been carried out (for example, see Japanese Patent No. 3168624), but satisfactory results have not yet been obtained.
DISCLOSURE OF INVENTION
The present invention solves the above problems and aims to develop a reactive dye composition and a dyeing method for dyeing cellulose fibers or cellulose fiber-containing fiber materials with excellent reproducibility, detergency, good dyeability, and high reproducibility. It is done.
In order to solve the above problems of the prior art, the present inventors have diligently researched the reactions containing a blue reactive dye composition containing a specific blue reactive dye or a specific red reactive dye and / or a specific yellow reactive dye. By using the dye composition, it has been found that the affinity and dyeing speed of each dye constituting these dye compositions are consistent, and that the cellulose fibers can be dyed with good uniformity and reproducibility, thus completing the present invention. .
That is, the present invention,
1. Blue reactive dye composition in free acid form, containing a blue reactive dye represented by formula (A) and a blue reactive dye represented by formula (1):
In formula (A),
R represents a hydrogen atom, a halogen atom or a C1-C4 alkoxy group. In addition, -SO 2 CH 2 CH 2 OSO 3 H groups are -SO 2 CH = CH 2 formed by decomposition It may be a guinea pig.
In formula (1),
m 1 represents an integer of 0 to 2,
R 1 and R 2 each independently represent a hydrogen atom or an alkyl group which may be substituted,
X 1 represents a halogen atom,
Y 1 is -SO 2 CH = CH 2 Or SO 2 CH 2 CH 2 Z 1 (Wherein Z 1 represents a group released by the action of an alkali).
2. Blue reactive dye composition as described in 1. and red reactive dye represented by following formula (2) and / or (3) as free acid form, and / or yellow reactive dye represented by formula (4) as free acid form. Reactive dye compositions containing:
In formula (2),
m 2 represents an integer of 0 to 2,
n 1 represents 0 or 1,
R 3 and R 4 each independently represent a hydrogen atom or an alkyl group which may be substituted,
X 2 represents a halogen atom,
Y 2 is -SO 2 CH = CH 2 Or SO 2 CH 2 CH 2 Z 2 (Wherein Z 2 represents a group released by the action of alkali).
In formula (3),
m 3 represents an integer of 0 to 2,
n 2 represents 0 or 1,
R 5 and R 6 each independently represent a hydrogen atom or an alkyl group which may be substituted,
X 3 represents a halogen atom,
Y 3 is -SO 2 CH = CH 2 Or SO 2 CH 2 CH 2 Z 3 (Wherein Z 3 represents a group released by the action of an alkali).
In formula (4),
m 4 represents an integer of 1 to 3,
R 7 and R 8 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an acylamino group or a ureido group,
R 9 and R 10 each independently represent a hydrogen atom or an alkyl group which may be substituted,
X 4 represents a halogen atom,
Y 4 is -SO 2 CH = CH 2 Or SO 2 CH 2 CH 2 Z 4 (Wherein Z 4 represents a group released by the action of an alkali).
3. The composition of the blue reactive dye represented by general formula (A) and the blue reactive dye represented by general formula (1) is 95 to 5 wt%: 5 to 95 wt%
4. Reactive dye composition containing the blue reactive dye composition as described in said 1. or 3. and red reactive dye represented by said General formula (2) and / or General formula (3),
5. The composition ratio of the blue reactive dye composition according to 1. or 3. above and the red reactive dye represented by the general formula (2) and / or general formula (3) is 99 to 50 wt%: 1 to 50 wt% Reactive dye compositions described in
6. The reactive dye composition according to the above 4., wherein the composition ratio of the red reactive dyes represented by the formulas (2) and (3) is 90 to 10% by weight: 10 to 90% by weight;
7. Dyeing method of a cellulose fiber or a cellulose fiber-containing fiber material characterized by using the reactive dye composition according to any one of 1. to 6.
8. Cellulose characterized in that the cellulose fiber or the cellulose fiber-containing fiber material is treated in a salt bath containing the blue reactive dye represented by the formula (A) and the blue reactive dye represented by the formula (1) as a free acid form. Dyeing method of fiber or cellulose fiber-containing fiber material,
9. Blue reactive dye represented by formula (A) as free acid form and blue reaction dye represented by formula (1) and red reaction represented by formula (2) and / or formula (3) in free acid form It provides a dyeing method of cellulose fibers or cellulose fiber-containing fiber materials, characterized in that the cellulose fibers or cellulose fiber-containing fiber materials are treated in a dye bath containing a yellow reactive dye represented by the formula (4) as a dye and / or a free acid form. do.
Best Mode for Carrying Out the Invention
In the blue reactive dye represented by the formula (A), preferred of R is a hydrogen atom, and a particularly preferred specific example of the blue reactive dye represented by the formula (A) is a blue reactive dye represented by the following formula (B). In the following formula, -SO 2 CH 2 CH 2 OSO 3 H group is -SO 2 CH = CH 2 which is formed by decomposition It may be a guinea pig. (Hereafter equal)
The blue reactive dye represented by the above formula (A) is described in Japanese Patent Application Laid-Open No. 1-24826 and the like, and can be synthesized as follows, for example.
First, the hydrazone compound represented by general formula (a-3) is synthesize | combined from the compound of general formula (a-1) and (a-2). Subsequently, the compound represented by the formula (a-4) is diazotized by a conventional method and coupled to the compound represented by the formula (a-3) to obtain the compound represented by the formula (a-5). A compound represented by the formula (A) can be obtained by reacting a copper complexing agent such as copper sulfate and finally esterifying it with sulfuric acid or the like.
In formula (A), a sulfone group and a carboxyl group are in free acid form, and R represents a hydrogen atom, a halogen atom or a C1-C4 alkoxy group.
The blue reactive dye represented by the above formula (B) is also synthesized in accordance with the above.
In the above formulas (1) to (4), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 and R 10 are hydrogen atoms or alkyl groups which may be substituted. Preferably, they are a hydrogen atom, a methyl group, and an ethyl group, and a hydrogen atom is especially preferable. As an alkyl group which may be substituted, for example, an alkyl group, hydroxy, cyano, C1-C4 alkoxy, carboxy, carbamoyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyloxy, sulfo, sulfamoyl, preferably C1-C4 alkyl group which may be substituted by halogen is mentioned.
Examples of the alkyl group include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, and the like. Examples of C 1 -C 4 alkoxy substituted with hydroxy or C 1 -C 4 alkoxy include 2 -Hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, 2,3-dihydroxybutyl, 3,4-dihydrate Hydroxybutyl, methoxymethyl, ethoxymethyl, 2-methoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 2-hydroxy-3-methoxypropyl, 3-ethoxypropyl, 2-hydroxy 3-methoxypropyl etc. are mentioned.
Examples of the C 1 -C 4 alkoxy group substituted with cyano include cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, and the like. Examples of the C 1 -C 4 alkoxy group substituted with halogen include chloromethyl, bromomethyl, 2-chloroethyl, 2-bromoethyl, 3-chloropropyl, 3-bromopropyl, 4-chlorobutyl, 4-bromobutyl, and the like. Examples of the carboxy-substituted C1-C4 alkyl group include, for example, carboxy. Methyl, 2-carboxyethyl, 3-carboxypropyl, 3-carboxybutyl, 1,2-dicarboxyethyl, and the like. Examples of the C1-C4 alkyl group substituted with carbamoyl include, for example, carbamoylmethyl and 2-carbo; Barmoylethyl, 3-carbamoylpropyl, 4-carbamoylbutyl, and the like.
Examples of the C 1 -C 4 alkyl group substituted with C 1 -C 4 alkoxycarbonyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 3-methoxycarbonylpropyl , 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 4-ethoxycarbonylbutyl, and the like. Examples of C1-C4 alkylcarbonyloxy include methylcarbonyloxymethyl and 2-methylcarbonyl. Oxyethyl, 2-ethylcarbonyloxyethyl, 3-methylcarbonyloxypropyl, 3-ethylcarbonyloxypropyl, 4-ethylcarbonyloxybutyl and the like.
Examples of the C 1 -C 4 alkyl group substituted by sulfo include sulfomethyl, 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, and the like. Examples of the C 1 -C 4 alkyl group substituted with sulfamoyl include sulfamoylmethyl, 2 -Sulfamoyl ethyl, 3-sulfamoylpropyl, 4-sulfamoylbutyl, etc. are mentioned.
In the general formula (4), examples of the alkyl group represented by R 7 and R 8 include C 1 -C 4 alkyl such as methyl and ethyl, and examples of the alkoxy group include C 1 -C 4 alkoxy such as methoxy and ethoxy. And methoxy groups are preferred. As acylamino group represented by R <7> , R <8> , acetylamino, propionylamino, etc. are mentioned, for example. Particularly preferred combinations of R 7 and R 8 include a hydrogen atom on the one hand and a ureido group on the other.
Moreover, as a group which detach | desorbs by the action of the alkali represented by Z <1> , Z <2> , Z <3> and Z <4> , a sulfuric acid ester group, a thiosulfate ester group, a phosphate ester group, an acetate ester group, a halogen atom, etc. are mentioned, for example. Preferably sulfuric acid ester groups. These ester groups are easily released in water, preferably in the presence of alkalis such as sodium carbonate, sodium bicarbonate, sodium hydroxide and the like.
Reaction dyes represented by formula (1) are described in Japanese Patent Application Laid-Open No. 1-12787, Japanese Patent Application Laid-Open No. 56-128380 (Patent Publication No. 62-1036), and the like. Reaction dyes represented by the formula (3) are described in the specification of European Patent No. 222575 and the like, and reaction dyes represented by the formula (4) are described in Japanese Patent Application Laid-Open No. 56-15481 and the like. It can manufacture according to this.
The dye represented by the formula (1) as the blue reactive dye is preferably a free acid form and a dye represented by the formula (5) or the formula (6), but is not limited thereto.
Although it does not specifically limit as a red reactive dye represented by General formula (2), The dye represented by a free acid form and represented by following General formula (7) is preferable.
Although it does not specifically limit as red reactive dye represented by General formula (3), The dye represented by following General formula (8) in free acid form is preferable.
In the present invention, the blue reactive dye composition contains a reactive dye represented by the general formula (A) and a reactive dye represented by the general formula (1) as essential components. The composition ratio of the reactive dye represented by the formula (A) and the reactive dye represented by the formula (1) is usually 95% by weight to 5% by weight: 5% by weight to 95% by weight, preferably 85% by weight to 15% by weight: 15% to 85% by weight, more preferably 75% to 55% by weight: 25% to 45% by weight. Moreover, reactive dyes other than the reaction dye represented by General formula (A) and the reaction dye represented by General formula (1) can also be used together. Reactive dyes that can be used in combination are preferably reaction dyes having the same kind of reactive groups, and may be used in combination with red or other color reactive dyes for toning (mixing several dyes to obtain the desired color). Can be.
The red reactive dye which can be used together is preferably a reaction dye represented by the formula (2) and / or the formula (3), more preferably a reaction represented by the formula (7) and / or the formula (8). Dye. The composition ratio of the blue reactive dye composition and the red reactive dye represented by Formula (2) and / or Formula (3) is usually 99% by weight to 50% by weight: 1% by weight to 50% by weight, preferably 99% by weight. To 70% by weight: 1% to 30% by weight, more preferably 99% to 80% by weight: 1% to 20% by weight.
The red reactive dyes preferably used in the present invention are composed of dyes represented by the formulas (2) and (3), preferably a combination of the dyes represented by the formula (7) and the formula (8). The composition ratio is usually 90% to 10% by weight: 10% to 90% by weight, preferably 80% to 20% by weight: 20% to 80% by weight, more preferably 70% to 40% by weight. : 30 wt% to 60 wt%. Moreover, reaction dyes other than the reaction dye represented by General formula (2) and General formula (3) can also be used together.
The reactive dyes represented by the formulas (2) and (3) can be used as the setting (fine-tuning color) component of the blue reactive dye composition of the present invention. In this case, 1% by weight to 3% by weight based on the blue reactive dye composition of the present invention is used.
Among the other reactive dyes that can be used in combination, a yellow dye may be a reactive dye represented by the general formula (4). The reaction dye represented by the formula (4) is preferably a dye represented by the following formula (9) and / or formula (10) in the form of a free acid, but is not limited thereto.
The reaction dyes represented by the formulas (1) to (10) are all present in free acid form or salt form thereof, and alkali metal salts or alkaline earth metal salts are preferable, and sodium salts, potassium salts and lithium salts are particularly preferable.
In the blue reactive dye composition and the reactive dye composition of the present invention, the blending method of each dye is not particularly limited. For example, a method of preparing each dye separately, then blending, blending in a reaction solution at the time of manufacture, and then drying and making a composition, or the same composition as each of the above compositions in a dye bath by dissolving each dye in a dye bath It is possible to employ a method of doing this. The mixing ratio of the blue reactive dye composition and the red reactive dye and / or the yellow reactive dye at that time is blended according to the desired color tone, and is not particularly limited. If necessary, the composition of the present invention may contain a known additive such as a concentration regulator, a dispersant, a leveling agent, a precipitation inhibitor, a metal ion blocking agent, a reducing agent and the like.
In the above, the dyes, additives in the case of dyeing the dye bath and the like by directly adding each of the dyes constituting the blue reactive dye composition or the reactive dye composition of the present invention and the above-described additives to the salt bath, the potting liquid and the printing foil The order of dissolving may be arbitrary order. The usage-amount of each chemical agent used can also be suitably determined according to the above.
In the dyeing method using the blue reactive dye composition and the reactive dye composition of the present invention, each amount of use is usually 0.005 to 15% (fiber mass,% owf) based on the fibers.
The blue reactive dye composition and the reactive dye composition of the present invention are useful for dyeing a cellulose fiber material and a fiber material containing the same. Examples of the fibers to be exemplified include single or mixed fibers of cellulose fibers such as cotton, hemp, rayon, polynosic, cupra, and lyocell. These fibers may also be mixed with blended fibers and other fibers such as polyester fibers, acetate fibers, polyacrylonitrile fibers, polyamide fibers such as wool, silk, nylon, and the like, or teaching materials.
In the present invention, the dyeing method itself can be carried out according to a known method such as the following method.
As a dyeing method, for example, in dyeing cellulose fibers such as cotton, the blue reactive dye composition and the reactive dye composition of the present invention are added to a salt bath according to a desired color and concentration, and a known inorganic neutral salt such as anhydrous glauber salt, salt, etc. Dyeing is performed alone or in combination with a binder such as sodium carbonate, sodium bicarbonate, sodium hydroxide, trisodium phosphate and the like. Although there is no restriction | limiting in particular also about the usage-amount of the inorganic neutral salt and acid binder used at this time, It is preferable to use at least 1 g / L. In addition, the inorganic neutral salt or the acid binder may be added to the salt bath at once or may be separately added. In addition, although dyeing aids, such as a softening agent and a leveling agent, in a bath may be used together by a well-known method, it is not specifically limited to these as a dyeing aid. Although dyeing temperature is 40-90 degreeC, 50-70 degreeC is preferable. The bath ratio is usually 1: 5 to 1:50 (chloride: dye bath).
In the continuous dyeing method, an acid binder such as sodium carbonate, sodium bicarbonate, sodium hydroxide, or the like is added alone or in combination to a dye potting solution, potted by a known method, dried, and dried or heated by a known method. One-bath potting method for dyeing and potting and drying the dye, and then known inorganic neutral salts, such as anhydrous glauber salt, salts and the like and acid binders, such as sodium hydroxide, sodium silicate and the like, dry or steamed by a known method Although the two-bath potting method of dyeing can be illustrated by doing it, it is not limited to these as a continuous dyeing method.
In the printing method, sodium arginate, emulsion arc or the like is used as an arc, and the printing arc containing a dye and an acid binder such as sodium bicarbonate is stamped by a known method, followed by drying or heating by a known method. It is carried out by.
After completion of the dyeing step, after washing with water and washing with water, washing is performed with a soaping bath containing 0.1 to 5 g / L of a commercially available soaping agent and the dyeing is finished.
The blue reactive dye composition, the reactive dye composition and the dyeing method of the present invention are excellent in various dyeing characteristics such as extremely good uniformity and reproducibility and good buildup in dyeing cellulose fibers and the fiber materials including them. Good dyeings can be obtained.
Hereinafter, an Example demonstrates this invention in more detail. In addition, "part" in the text means parts by weight unless otherwise specified.
Example 1
Table 1 shows the combinations of reaction dyes and their amounts used. In Table 1, C.I. Reactive means color index generic name.
Table 1 (Composition Composition)
Compounding Example 1 (Invention of the Invention)
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Formulation Example 2 (Comparative)
Blue Reaction Dye
C.I.Reactive Blue 221 Part 0.39
Red Reaction Dye
C.I.Reactive Red 195
Yellow Reaction Dye
C.I.Reactive Yellow 145 0.59
Formulation Example 3 (Comparative)
Blue Reaction Dye
C.I.Reactive Blue 222
Red Reaction Dye
C.I.Reactive Red 195 Part 0.14
Yellow Reaction Dye
C.I.Reactive Yellow 145
○ Expense dependence test
(1) dyeing at bath ratio 1:10
Water was added to each dye shown in Table 1 and 20 parts of anhydrous sodium sulfate, and the total amount of 490 parts of salt baths was produced. 50 parts of cotton Maryas was thrown into this dye bath, and it heated up at 60 degreeC for 20 minutes. After 20 minutes of treatment at 60 ° C, 10 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes. Subsequently, after washing with water and hot water, after soaping at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing a commercially available soaping agent (same as 1 g / L of Scoral C-1200 Fukuhiro Chemical Co., Ltd.), washing with water and drying To give a tea-colored dyeing.
(2) dyeing at 1:30
Water was added to each dye shown in Table 1 and 60 parts of anhydrous sodium sulfate, and the total amount of 1470 parts of salt baths was produced. 50 parts of cotton Maryas was thrown into this dye bath, and it heated up at 60 degreeC for 20 minutes. After 20 minutes of treatment at 60 ° C, 30 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes. Subsequently, after washing with water and hot water, the product was soaped at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing a commercially available soaping agent, and then washed with water and dried to obtain a light colored dye.
(3) Judgment method
The color difference of the dye obtained at the bath ratio 1:30 based on the dye obtained at the bath ratio 1:10 was visually determined.
○: less color difference
×: color difference
○ Temperature dependency test
(1) 55 ℃ dyeing
Water was added to each of the dyes shown in Table 1 and 40 parts of anhydrous sodium sulfate to prepare a total amount of 980 parts of a salt bath. 50 parts of cotton maryas were thrown into this dye bath, and it heated up at 55 degreeC for 20 minutes. After 20 minutes of treatment at 55 占 폚, 20 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes. Subsequently, after washing with water and hot water, the resultant was soaped at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing the soaping agent, followed by washing with water and drying to obtain a light colored dye.
(2) 65 ℃ dyeing
Dyeing was carried out in the same manner as in the 55 ° C dyeing except that the dyeing temperature was changed to 65 ° C.
(3) Judgment method
The color difference of the dye obtained by 65 ° C. staining was determined based on the dye obtained by 55 ° C. dyeing.
○: less color difference
×: color difference
○ Absorption, fixation behavior test
Water was added to each of the dyes shown in Table 1 and 40 parts of anhydrous sodium sulfate to prepare four salt baths in total of 980 parts. 50 parts of cotton Maryas was added to each salt bath, and after heating up at 60 degreeC for 20 minutes, each salt bath was processed by the method of following (1)-(4), and absorption and fixation behavior were tested.
(1) After heating up at 60 degreeC, after hold | maintaining at 60 degreeC for 20 minutes, the salt sac was taken out from one salt bath, it was divided into 2 parts, and the after-treatment of following (A)-(B) was performed.
(A) The application was finished, dehydrated and naturally dried (absorbent fabric).
(B) After washing and washing the dyed cloth with water, it was soaped at 100 degreeC for 15 minutes in 1000 parts of aqueous solutions containing the said soaping agent, and it washed with water and dried (fixed cloth).
(2) 20 parts of sodium carbonate was added (1000 parts in total of a salt bath), and after dyeing at the same temperature for 5 minutes, one salt sac was taken out, and this was followed by two minutes to perform post-treatment of (A) or (B), respectively.
(3) 20 parts of sodium carbonate were added (1000 parts in total of a salt bath), and after dying at the same temperature for 10 minutes, one salt saline was taken out, and this was followed by two minutes to perform post-treatment of (A) or (B), respectively.
(4) 20 parts of sodium carbonate was added (1000 parts in total of a salt bath), and after dying at the same temperature for 40 minutes, one salt saline was taken out, and this was followed by two minutes to perform post-treatment of (A) or (B), respectively. .
Judgment method (a)
In each of (1)-(4), the color difference of the said (B) process cloth was visually determined based on the said (A) process cloth.
○: none of (1) to (4) color difference
×: (1) ~ (4) where there is a large difference in color
Judgment method (b)
In the treatment cloth (B), the degree of color change was visually determined in the order of (1), (2), (3), and (4).
○: (1) to (4) all the same color system
(Good fixation speed balance of three primary colors)
×: large color change from (1) to (4)
(Poor fixation speed balance of three primary colors)
Table 2 shows the results of comparison of bath independence, temperature dependence, absorption and fixation behavior in the compounding example 1 (original invention) and the compounding examples 2 to 3 (for comparison).
Table 2 (Test Results)
Bath ratio-dependent temperature-dependent absorption, seizure behavior
Judgment method (a) Judgment method (b)
Formulation Example 1 ○ ○ ○ ○
Formulation Example 2 × △ × ×
Formulation Example 3 × △ × ×
Only when dyeing is performed in the combination of Formulation Example 1 (the present invention), even when the dyeability of the yellow reaction dye, the red reaction dye and the blue reaction dye is consistent, and the dyeing conditions such as bath ratio, dyeing temperature and dyeing time are varied. The color change is small and the fixing speed is almost matched, so dye reproducibility is excellent.
Examples 2-15
Water was added to 40 parts of anhydrous sodium sulfate using the combination and the amount (part) of dye shown in Table 3 instead of the combination and the amount of the compounding example 1 of Example 1, respectively, and the total amount of 980 parts of salt baths were produced, respectively. 50 parts of cotton Maryas was added to this dye bath, and it heated up at 60 degreeC for 20 minutes. After 20 minutes of treatment at 60 ℃, 20 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes.
Subsequently, after washing with water and hot water, the resultant was soaped at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing the soaping agent, followed by washing with water and drying to obtain a dye.
Table 3
Example 2
Blue Reaction Dye
0.28 parts of dye of formula (B)
0.15 parts of dye of formula (5)
Example 3
Blue Reaction Dye
0.55 parts of dye of formula (B)
0.31 parts of dye of formula (5)
Red Reaction Dye
0.05 part of dye of formula (7)
Example 4
Blue Reaction Dye
0.60 parts of dye of formula (B)
0.28 parts of dye of formula (5)
Red Reaction Dye
0.04 parts of dye of formula (8)
Example 5
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 6
Blue Reaction Dye
0.38 parts of dye of formula (B)
0.22 parts of dye of formula (5)
Red Reaction Dye
0.22 parts of dye of formula (7)
0.18 parts of dye of formula (8)
Example 7
Blue Reaction Dye
0.45 parts of dye of formula (B)
0.25 parts of dye of formula (5)
Red Reaction Dye
0.06 parts of dye of formula (7)
0.04 parts of dye of formula (8)
Yellow Reaction Dye
0.20 parts of dye of formula (9)
Example 8
Blue Reaction Dye
0.13 parts of dye of formula (B)
0.07 parts of dye of formula (6)
Red Reaction Dye
0.39 parts of dye of formula (7)
0.32 parts of dye of formula (8)
Yellow Reaction Dye
0.10 parts of dye of formula (9)
Example 9
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (6)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.57 parts of dye of formula (10)
Example 10
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.20 parts of dye of formula (7)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 11
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (6)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 12
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.08 parts of dye of formula (7)
0.12 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 13
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.14 parts of dye of formula (7)
0.06 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 14
Blue Reaction Dye
0.27 parts of dye of formula (B)
0.09 parts of dye of formula (5)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 15
Blue Reaction Dye
0.16 parts of dye of formula (B)
0.20 parts of dye of formula (5)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
The color of the obtained dyeing material was Example 2 blue, Example 3 and Example 4 ultramarine blue, Example 6 purple, Example 7 green, Example 8 light green, Examples 5 and 9 to 15 Was dark blue.
In any of the combinations of Examples 2 to 15, various dyeing characteristics such as extremely good leveling and reproducibility were excellent, and all fastnesses such as light, sweat, light and chlorine water were also excellent.
Examples 16-21
Water was added to 40 parts of anhydrous sodium carbonate using the combination of dye shown in Table 4, and the total amount of 980 parts of salt baths was respectively produced. 50 parts of rayon muslin were added to this dye bath, and it heated up at 60 degreeC for 20 minutes. After 20 minutes of treatment at 60 ℃, 20 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes.
Subsequently, after washing with water and hot water, the resultant was soaped at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing the soaping agent, followed by washing with water and drying to obtain a dyeing product.
Table 4
Example 16
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.11 parts of dye of formula (7)
0.09 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 17
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (6)
Red Reaction Dye
0.13 parts of dye of formula (7)
0.07 parts of dye of formula (8)
Yellow Reaction Dye
0.57 parts of dye of formula (10)
Example 18
Blue Reaction Dye
0.27 parts of dye of formula (B)
0.09 parts of dye of formula (5)
Red Reaction Dye
0.12 parts of dye of formula (7)
0.10 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 19
Blue Reaction Dye
0.23 parts of dye of formula (B)
0.13 parts of dye of formula (5)
Red Reaction Dye
0.14 parts of dye of formula (7)
0.06 parts of dye of formula (8)
Yellow Reaction Dye
0.54 parts of dye of formula (9)
Example 20
Blue Reaction Dye
0.45 parts of dye of formula (B)
0.25 parts of dye of formula (5)
Red Reaction Dye
0.06 parts of dye of formula (7)
0.04 parts of dye of formula (8)
Yellow Reaction Dye
0.20 parts of dye of formula (9)
Example 21
Blue Reaction Dye
0.13 parts of dye of formula (B)
0.07 parts of dye of formula (5)
Red Reaction Dye
0.39 parts of dye of formula (7)
0.32 parts of dye of formula (8)
Yellow Reaction Dye
0.10 parts of dye of formula (9)
The colors of the obtained dyeings were Examples 16 to 19 as light blue, Example 20 was green, and Example 21 was pale color.
In any of the combinations of Examples 16 to 21, it was excellent in various dyeing characteristics such as extremely good leveling and reproducibility, good buildup properties, and excellent fastness of light, sweat, light, chlorine water and the like.
Example 22
As the blue reactive dye, 3.30 parts of the dye of formula (B), 1.85 parts of the dye of formula (5), 7.20 parts of the dye of formula (7) as the red reactive dye, 5.06 parts of dye of formula (8), Water was added to 10 parts of sodium metanitrobenzenesulfonic acid, 20 parts of sodium hydrogencarbonate, and 1 part of sodium arginates using 12.00 parts of dyes of 9), and a total volume of 1000 parts of a bath was prepared. After potting cotton in this bath, it was squeezed by a mangle (mangle) at 60%. The hole treated fabric was dried at 100 ° C. for 5 minutes and then steamed at 100 ° C. for 5 minutes to fix the dye. Subsequently, after washing with water and hot water, after soaping at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing the soaping agent, washing with water and drying to obtain a dyeing product.
The color of the obtained dye was reddish-brown.
Also in the continuous dyeing, the dyeing properties were extremely good, the reproducibility was very good, the buildup properties were excellent, and the fastness of light, sweat, light, chlorine water and the like were also excellent.
Example 23
6.33 parts of dye of formula (B), 3.55 parts of dye of formula (5) as a blue reactive dye, 10.25 parts of dye of formula (7), 7.33 parts of dye of formula (8) as a yellow reactive dye, Water was added to 100 parts of urea, 20 parts of sodium hydrogencarbonate, 10 parts of sodium metanitrobenzene sulfonate, and 25 parts of sodium arginate using 17.00 parts of dyes of 9) to prepare a printing volume color printing part of 1000 parts. This color arc was imprinted on the cotton, dried at 100 ° C. for 5 minutes, and then steamed at 100 ° C. for 5 minutes to fix the dye. Subsequently, after washing with water and hot water, the product was soaped at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing a commercially available soaping agent, and then washed with water and dried to obtain a dyeing product.
The color of the obtained dye was reddish-brown. In printing, the dyeing properties were extremely good, the reproducibility was extremely good, the buildup properties were excellent, and the fastness of light, sweat, light, and chlorine water was also excellent.
By using the blue reactive dye composition, the reactive dye composition or the dyeing method of the present invention, the cellulose fibers or the cellulose-containing fibers can be dyed with good affinity, reactivity as well as reproducibility, uniformity and fastness with good balance.
Claims (13)
Applications Claiming Priority (2)
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| JP2003044411 | 2003-02-21 | ||
| JPJP-P-2003-00044411 | 2003-02-21 |
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|---|---|
| KR (1) | KR101075939B1 (en) |
| CN (1) | CN1331949C (en) |
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| WO (1) | WO2004074385A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5682947B2 (en) * | 2009-05-28 | 2015-03-11 | 日本化薬株式会社 | Reactive dye composition and dyeing method using the same |
| CN101817997B (en) * | 2009-11-16 | 2013-05-08 | 天津德凯化工股份有限公司 | Dye |
| CN101709158B (en) * | 2009-11-16 | 2013-11-13 | 天津德凯化工股份有限公司 | Reactive dye and preparation method thereof |
| CN101709156B (en) * | 2009-11-16 | 2013-11-13 | 天津德凯化工股份有限公司 | Dark blue dye suitable for dyeing nylon |
| CN101812244B (en) * | 2009-11-16 | 2013-06-19 | 天津德凯化工股份有限公司 | Reactive dye for dyeing nylon and preparation method thereof |
| CN102295840B (en) * | 2010-06-25 | 2013-12-11 | 上海雅运纺织化工股份有限公司 | Navy blue reactive dye composition and dyeing application thereof to fibers |
| CN102311667B (en) * | 2010-07-08 | 2013-12-04 | 上海雅运纺织化工股份有限公司 | Navy reactive dye composition and dying application thereof on fiber |
| CN103013174A (en) * | 2012-12-17 | 2013-04-03 | 浙江亿得化工有限公司 | Composite reactive dye composition and use method |
| CN105348854B (en) * | 2014-08-22 | 2017-03-22 | 湖北丽源科技股份有限公司 | Blue reactive dye |
| WO2019044603A1 (en) * | 2017-09-01 | 2019-03-07 | 日本化薬株式会社 | Reactive dye composition and dyeing method using same |
| CN114350177B (en) * | 2021-12-25 | 2023-10-17 | 苏州科法曼化学有限公司 | Blue dye composition and application thereof |
| CN114292530B (en) * | 2021-12-25 | 2023-11-21 | 苏州科法曼化学有限公司 | Blue reactive dye composition and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2001335719A (en) | 2000-05-26 | 2001-12-04 | Sumitomo Chem Co Ltd | Reactive dye mixture and its application |
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| DE19511689A1 (en) * | 1995-03-30 | 1996-10-02 | Hoechst Ag | Mixture of blue-coloring fiber-reactive dyes and their use for dyeing fiber material containing hydroxyl and / or carbonamide groups |
| JP3405135B2 (en) * | 1997-06-30 | 2003-05-12 | 住友化学工業株式会社 | Reactive dye mixture and dyeing or printing method using the same |
| US6143039A (en) * | 1999-04-12 | 2000-11-07 | Dystar Textilfarben Gmbh & Co. | Blue dye mixtures of fiber-reactive copper complex formazan dyes |
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2004
- 2004-02-20 TW TW093104286A patent/TW200502327A/en not_active IP Right Cessation
- 2004-02-20 CN CNB2004800045007A patent/CN1331949C/en not_active Expired - Lifetime
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| JP2001335719A (en) | 2000-05-26 | 2001-12-04 | Sumitomo Chem Co Ltd | Reactive dye mixture and its application |
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| KR20050103917A (en) | 2005-11-01 |
| TWI343401B (en) | 2011-06-11 |
| TW200502327A (en) | 2005-01-16 |
| CN1751103A (en) | 2006-03-22 |
| CN1331949C (en) | 2007-08-15 |
| WO2004074385A1 (en) | 2004-09-02 |
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