CN113683904B - Red dye composition for dyeing and printing - Google Patents
Red dye composition for dyeing and printing Download PDFInfo
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- CN113683904B CN113683904B CN202111015754.0A CN202111015754A CN113683904B CN 113683904 B CN113683904 B CN 113683904B CN 202111015754 A CN202111015754 A CN 202111015754A CN 113683904 B CN113683904 B CN 113683904B
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- 238000007639 printing Methods 0.000 title claims abstract description 85
- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 238000004043 dyeing Methods 0.000 title abstract description 41
- 239000001044 red dye Substances 0.000 title description 19
- 239000000975 dye Substances 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000000986 disperse dye Substances 0.000 claims abstract description 39
- 238000005406 washing Methods 0.000 claims abstract description 35
- 239000004753 textile Substances 0.000 claims abstract description 30
- 239000007788 liquid Substances 0.000 claims abstract description 22
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 238000001035 drying Methods 0.000 claims description 39
- 238000010025 steaming Methods 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 8
- -1 carboxymethyl sulfonyl Chemical group 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 4
- 239000012498 ultrapure water Substances 0.000 claims description 4
- 239000006194 liquid suspension Substances 0.000 claims description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 238000007730 finishing process Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008399 tap water Substances 0.000 claims description 2
- 235000020679 tap water Nutrition 0.000 claims description 2
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 2
- 238000010790 dilution Methods 0.000 abstract description 10
- 239000012895 dilution Substances 0.000 abstract description 10
- 239000002002 slurry Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 239000012954 diazonium Substances 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 238000010021 flat screen printing Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- WEAJAFRCXNDNBY-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]propanamide Chemical compound CCN(CC)C1=CC=CC(NC(=O)CC)=C1 WEAJAFRCXNDNBY-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- DJJYQAFPHMVIFW-UHFFFAOYSA-N 2-(4-amino-3-chlorophenyl)sulfonylacetic acid Chemical compound ClC=1C=C(C=CC1N)S(=O)(=O)CC(=O)O DJJYQAFPHMVIFW-UHFFFAOYSA-N 0.000 description 1
- ZDORFLXCSSFUIE-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-chloro-4-nitrophenyl)diazenyl]-3-(propanoylamino)anilino]ethyl acetate Chemical compound CCC(=O)NC1=CC(N(CCOC(C)=O)CCOC(C)=O)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl ZDORFLXCSSFUIE-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- 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
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
- C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention relates to a liquid dye composition, in particular to a red liquid dye composition for dyeing and printing and application thereof. The composition consists of 15-60% of hydrophobic dye monomer, 0.05% -5% of hydrophilic dye monomer and 35% -84.5% of water according to weight percentage; the dyeing and printing process of the disperse dye slurry composition for dyeing and printing adopts the processes of water washing, soaping and the like, the COD of washing water of washed textiles is between 30 and 800ppm, part of varieties is less than 200ppm, and part of varieties is less than 50ppm; chromaticity (dilution factor) is less than 200, chromaticity (dilution factor) of partial variety is less than 80, chromaticity (dilution factor) of partial variety is less than 30.
Description
Technical Field
The invention relates to a dye composition, in particular to a red dye composition for dyeing and printing and application thereof in textile dyeing and printing.
Background
Disperse dyes generally do not contain hydrophilic groups and belong to nonionic dyes. Disperse dyes obtained by synthesis cannot generally be used directly for dye, printing applications and require commercial processing of the dyes to form dispersions of suitable particle size or powdered products readily dispersible in water. In the commercialized processing process, in order to enable the hydrophobic disperse dye to be sufficiently wetted and dispersed and have proper printing and dyeing application performance, a large amount of water-soluble anionic or nonionic auxiliary agents are generally required to be added, and the use amount of the auxiliary agents in the commercial disperse dye is generally larger than that of the dye by weight. These auxiliaries generally do not dye fibers, and can enter into dye baths or washing water in the application process of printing and dyeing, and become a main source of COD of the printing and dyeing wastewater.
The energy saving and emission reduction is a main direction of technology upgrading in the printing and dyeing industry all the time, the consumption of an auxiliary agent in disperse dyes is reduced, the COD of printing and dyeing wastewater can be reduced from the root, the method is an important direction of energy saving and emission reduction of the disperse dyes in recent years, chinese patent No. CN105970671A, a dyeing and coating integrated dyeing and printing slurry composition, CN106049091A, a dyeing and coating integrated dyeing and printing dye slurry composition, CN106087464A, a dyeing and printing process and the adopted dyeing and coating integrated technology are used as a novel energy saving and emission reduction technology, the consumption of the auxiliary agent in the conventional disperse dyes is reduced by 50-70%, a certain amount of anionic and nonionic auxiliary agents are still used, and the higher COD in the printing and dyeing wastewater can be brought.
Chinese patent ZL96115131.5 discloses a kind of water-temporary soluble disperse dye, wherein carboxymethyl sulfonyl is introduced into a hydrophobic disperse dye matrix, so that the disperse dye has the property of being soluble in water, and conventional disperse dye auxiliary agents are not required to be added in the processing and application processes. Under the high temperature condition of dye dyeing, the water-soluble dye undergoes decarboxylation reaction to release CO2 gas, and is converted into nonpolar disperse dye to dye the fiber or textile. The dye can be processed and used without adding auxiliary agents, but is limited by different dye parent structures, the decarboxylation reaction temperature and reaction speed of the carboxymethyl sulfonyl are different, the synchronous dyeing of the blended dye is greatly influenced, and meanwhile, the relative manufacturing cost is higher than that of the traditional commercial disperse dye and is not commonly adopted by the industry to date.
Chinese patent CN111019393a discloses a liquid composition containing a disperse dye for yellow dyeing and printing. The dye composition has hydrophilic and hydrophobic dye monomers, does not contain a dispersing agent commonly used in commonly dispersed dyes, has better fastness performance, does not need a complex water washing process, does not generate high COD and high chromaticity sewage, and is a cleaner dispersed dye product. However, the technical scheme is limited to a part of yellow disperse dye varieties, and the polarity of conjugated groups and the structure of dye among the disperse dye varieties with different colors are greatly different, and the dye adopting the patent structure is not suitable for other varieties except yellow, while the diazo component or the coupling component of the azo dye introduces carboxymethyl sulfonyl at different substitution positions, the reflection wavelength of the dye cannot be greatly influenced. This causes the disadvantage of incomplete chromatography of the technology of this patent, which is disadvantageous for full-color applications,
disclosure of Invention
The main purpose of the invention is to provide an additive-free liquid red disperse dye composition, which eliminates anionic or nonionic additives in disperse dyes for conventional dyeing and printing, reduces COD of wastewater in the dyeing application process, and further simplifies the disperse dye application process, so that the additive-free liquid red disperse dye composition is suitable for the environment-friendly dyeing and printing process of the disperse dyes.
In order to achieve the above purpose, the invention adopts the technical scheme that:
a red liquid dye composition for dyeing and printing comprises, by weight, 15-60% of hydrophobic dye monomers, 0.05% -5% of hydrophilic dye monomers and 35% -84.5% of water;
the hydrophobic dye monomer is one or more of disperse dyes in the formula (I);
r1 is selected from-Cl and-CN;
r2 is selected from-H, -NHCOCH 3 、-NHCOCH 2 CH 3 ；
R3 and R4 may be the same or different and are selected from-CH 2 CH 3 、-CH 2 CH 2 CN、-CH 2 CH 2 OCOCH 3 ；
The hydrophilic dye monomer is one or more of azo compounds containing carboxymethyl sulfonyl shown in a formula (II);
r5 and R6 can be the same or different and are selected from-H or halogen;
r7 is selected from-H or-OCH 3 ；
R8 is selected from the group consisting of-NHCOCH 3 、-NHCOCH 2 CH 3 or-NHCOC 6 H 5 ；
R9 and R10 may be the same or different and are selected from-CH 2 CH 3 、-CH＝CHCH 2 or-CH 2 CH 2 OCOCH 3 ；
The water is one or more of tap water, deionized water, distilled water, high-purity water and ultrapure water.
The red liquid dye composition for dyeing and printing is prepared through one-bath synthesis or separate preparation and refining.
The independent preparation is that the hydrophobic dye monomer and the hydrophilic dye monomer are mixed together in a physical mixing mode during refining processing, and the uniform and stable liquid suspension disperse dye composition with the particle size less than 1 micron is obtained through dispersion grinding.
The one-bath synthesis is to adopt a diazonium salt mixture of diazonium components contained in each of a hydrophobic monomer and a hydrophilic monomer to carry out a common coupling reaction with the same coupling component, so as to obtain the liquid suspension disperse dye composition with the original particle size less than 1 micrometer.
The dye composition is applied to dyeing and printing processes.
The dye composition is applied to dyeing and printing processes, and the specific process is selected from the following steps: textile, printing, drying, steaming, water washing, soaping, water washing, drying, finishing and printing to obtain a finished product; textile, printing, drying, steaming, water washing, drying, finishing and printing to obtain a finished product; textile, printing, drying, steaming, drying, finishing and printing finished products; textile, printing, drying, baking, water washing, soaping, water washing, drying, finishing and printing to obtain a finished product; textile, printing, drying, baking, water washing, drying, finishing and printing finished products; textile, printing, drying, baking, finishing, printing finished product and the like. More specifically, the technical process is to sequentially print, dry, color and finish the textile to be treated, thereby obtaining a printed finished product.
The color development and finishing process can be washed and dried; the color development temperature is 160-210 ℃; the color development time is 1-30 minutes; the color development adopts a steaming or baking mode; the washing can be performed by multiple washing and/or soaping.
The color development adopts a steaming or baking mode; the washing can be performed by adopting a plurality of washing and/or soaping modes.
Further, the process comprises the steps of printing, drying, steaming, washing, soaping, washing, drying and finishing the textile to be treated in sequence, so as to obtain a printed finished product; wherein the steaming temperature is 160-210 ℃ and the steaming time is 1-30 minutes.
The process comprises the steps of printing, drying, steaming, washing, drying and finishing the textile to be treated in sequence, so as to obtain a printed finished product; wherein the steaming temperature is 160-210 ℃ and the steaming time is 1-30 minutes.
The process comprises the steps of printing, drying, steaming and finishing textiles to be treated in sequence, and further obtaining printed finished products, wherein the steaming temperature is 160-210 ℃ and the steaming time is 1-30 minutes.
The process comprises the steps of printing, drying, baking, washing, soaping, washing, drying and finishing the textile to be treated in sequence, and further obtaining a printed finished product, wherein the baking temperature is 160-210 ℃ and the baking time is 1-30 minutes.
The process comprises the steps of printing, drying, baking, washing, drying and finishing the textile to be treated in sequence, so as to obtain a printed finished product, wherein the baking temperature is 160-210 ℃, and the baking time is 1-30 minutes.
The process comprises the steps of printing, drying, baking and finishing the textile to be treated in sequence, so as to obtain a printed finished product, wherein the baking temperature is 160-210 ℃ and the baking time is 1-30 minutes.
The steaming or baking temperature is 160-190 ℃, and the steaming or baking time is 1-10 minutes.
If the dyeing and printing processes are selected from the processes of water washing, soaping and the like, the COD of washing water of washed textiles is between 30 and 800ppm, part of varieties is less than 200ppm, and part of varieties is less than 50ppm; chromaticity (dilution factor) is less than 200, chromaticity (dilution factor) of partial variety is less than 80, chromaticity (dilution factor) of partial variety is less than 30.
Compared with the prior art, the invention has the following advantages:
1. the invention combines the dye hydrophilic component with specific structure required by red non-auxiliary dye with the conventional structure hydrophobic disperse dye to prepare the liquid disperse dye with the particle diameter less than or equal to 0.7 mu m under the non-auxiliary condition, thereby having better dispersion performance and application performance;
2. the color gamut range of the disperse dye in the prior art is widened, and wider color matching application is facilitated;
3. the composition has higher strength, adopts the conventional red disperse dye as a main component, has various performances and color lights similar to those of the conventional disperse dye, and is convenient to replace and use.
The dyeing and printing process of the disperse dye slurry composition for dyeing and printing adopts the processes of water washing, soaping and the like, the COD of washing water of washed textiles is between 30 and 800ppm, part of varieties is less than 200ppm, and part of varieties is less than 50ppm; chromaticity (dilution factor) is less than 200, chromaticity (dilution factor) of partial variety is less than 80, chromaticity (dilution factor) of partial variety is less than 30.
The specific embodiment is as follows:
the following description of the embodiments of the present invention is further provided in connection with the accompanying examples, and it should be noted that the embodiments described herein are for the purpose of illustration and explanation only, and are not limiting of the invention.
Example 1
Preparation of diazonium salts of hydrophilic components
To a 100mL three-necked flask cooled by an ice-salt bath at a temperature below-5℃was added 0.04mol (9.99 g) of 2-chloro-4-carboxymethyl sulfonylaniline, 24mL of water and 10g of crushed ice, 0.06mol (5.13 mL) of 36.5% concentrated hydrochloric acid was added under stirring, the temperature in the reaction flask was lowered to-5℃and a solution of 0.04mol (7.88 g,35% sodium nitrite aqueous solution) of sodium nitrite was rapidly added under the liquid surface, about 24g of crushed ice was added, the temperature of the reaction solution was kept at-5℃to 0℃and, after 3 to 5 minutes of reaction, the microscopic blue color was measured with starch potassium iodide, and the coupling was immediately carried out under stirring for 5 minutes.
Preparation of hydrophilic component red-1 containing carboxymethyl sulfonyl
To a 250ml beaker was added 0.04mol (13.46 g) of 3-propionylamino-N, N-diethylaniline, 36ml of water, 0.0468mol (4 ml) of 36% concentrated hydrochloric acid, stirred until completely dissolved, and 30g of ice was added and cooled to 0 ℃. Adding the diazonium salt solution into the coupling component in a trickle manner under stirring, adding about 35g of ice, controlling the reaction temperature at-5-0 ℃, adding 0.0372mol (3.2 ml) of 36% concentrated hydrochloric acid, controlling the pH value of the reaction solution to be less than 1, adding for about 50min, adding the diazonium component, naturally heating to 10 ℃ under stirring, reacting for 5h, filtering, washing with 40ml of water with pH value of 2-3, and filtering to obtain 58.86g (dried 23.15 g) of red dye wet filter cake with the following formula, wherein the yield is 96.94% and the lambda max is 492nm.
(3) Liquid red dye composition 1
Adding 629.20g of the hydrophilic component red-1 wet filter cake prepared in the step (2) and water into a dispersing tank, dispersing and stirring to dissolve the hydrophilic component red-1 wet filter cake completely, and adding 311.94g of dye with the following structure into the dispersing tank:
starting the dispersing machine, dispersing at high speed for 15min, regulating the pH value to 5.5 by ammonia water, continuously dispersing for 2 hours, and then pumping the dispersion slurry into a horizontal sand mill for circularly grinding for 4 hours to obtain the red liquid disperse dye composition 1, 1000g, wherein the fineness d50=0.68+/-0.2 mu m and the pH value=5.1.
According to the requirements of GB/T2374-2007 dye dyeing measurement, the red dye composition prepared by the method is adopted for flat screen printing, and the printing process comprises the following steps: textile, printing, drying, baking, finishing and printing to obtain a finished product, wherein: the baking temperature was 100℃for 10 minutes and the baking temperature was 200℃for 1 minute. Each item of detection data of the printing finished product is as follows:
example 2
Preparation of diazonium salts of hydrophilic components
The procedure is as in example 1.
Preparation of diazonium salts of hydrophobic components
1mol (172.6 g) of o-chloro-p-nitroaniline, 950mL of water and 375g of crushed ice are added into a 3000mL three-neck flask cooled by an ice salt bath with stirring and below-5 ℃, 2.5mol (214 mL) of 36.5% concentrated hydrochloric acid is added under stirring, the temperature of the materials in a reaction bottle is reduced to-5 ℃, 1mol (197.5 g,35% sodium nitrite aqueous solution) of sodium nitrite solution is quickly added under the liquid level, about 500g of crushed ice is added, the temperature of the reaction solution is kept at-5 ℃ to 0 ℃, microscopic blue is tested by using starch potassium iodide after 30min of reaction, and the coupling is immediately carried out under stirring for 5 min.
Preparation of mixed red dye cake
To a 10L reaction flask was added 1.04mol (349.96 g) of 3-propionylamino-N, N-diethylaniline, 3860ml of water, 1.2168mol (104 ml) of 36% concentrated hydrochloric acid were added dropwise, and the mixture was stirred until it was completely dissolved, and 1000g of ice was added and cooled to 0℃to obtain a coupling component. Then adding the two diazonium salt solutions into the obtained coupling component in a trickling way at the same time under stirring, adding about 1000g of ice, controlling the reaction temperature to be between-5 ℃ and 0 ℃, simultaneously adding 1.2168mol (104 ml) of 36% concentrated hydrochloric acid, controlling the pH value of the reaction solution to be less than 1, adding the diazonium component for about 50min, naturally heating to 10 ℃ under stirring, reacting for 5h, filtering, washing with 2500ml of water with pH=2-3, filtering to obtain 1258.37g (dried 520.33 g) of red dye wet filter cake with the following mixing yield of 96.24 percent.
Preparation of liquid Red dye composition 2
Adding the filtered mixed dye wet filter cake into a 3000ml beaker, adding 442g of water, stirring uniformly, slowly neutralizing the pH of the reaction solution to about 5.5 by using ammonia water under the high-shear emulsification condition of 8000rpm, neutralizing for 2 hours, and continuing high-shear emulsification for 1 hour after the neutralization is finished to obtain about 1700g of liquid red dye composition 2, wherein the fineness d50=0.66+/-0.2 mu m, and the pH=5.5.
According to the requirements of GB/T2374-2007 dye dyeing measurement, the red dye composition prepared by the method is adopted for flat screen printing, and the printing process comprises the following steps: textile, printing, drying, baking, finishing and printing to obtain a finished product, wherein: the baking temperature was 100℃for 10 minutes and the baking temperature was 200℃for 1 minute. Each item of detection data of the printing finished product is as follows:
examples 3 to 6
The liquid red dye compositions of examples 3 to 10 were prepared by the similar method to the method of example 1, in which the same amount of hydrophobic red-1 as that of example 1 was used in the similar method to the method of example 1, in which the same amount of hydrophilic components red 2 to 9 were prepared in the similar method to the method of example 1, in which step (3) was used, and water was added to 1000g, and the liquid red dye compositions of examples 3 to 10 were prepared by the similar method to the method of example 1, respectively, and the specific corresponding structures were as follows:
according to the requirements of GB/T2374-2007 dye dyeing measurement, the red dye composition prepared by the method is adopted for flat screen printing, and the printing process comprises the following steps: textile, printing, drying, baking, finishing and printing to obtain a finished product, wherein: the baking temperature was 100℃for 10 minutes and the baking temperature was 200℃for 1 minute. Each item of detection data of the printing finished product is as follows:
examples 11 to 15
An equimolar amount of a filter cake of the hydrophilic red component-1 prepared according to the steps (1) and (2) in example 1 was mixed with 0.6mol of the hydrophobic red component in examples 11 to 14, respectively, and the mixture was made up to 1000g with water, and after dispersion-milling by a similar method to example 1, each of the liquid red dye compositions in examples 11 to 14 was prepared, respectively, and the specific corresponding structures were as follows:
according to the requirements of GB/T2374-2007 dye dyeing measurement, the red dye composition prepared by the method is adopted for flat screen printing, and the printing process comprises the following steps: textile, printing, drying, baking, finishing and printing to obtain a finished product, wherein: the baking temperature was 100℃for 10 minutes and the baking temperature was 200℃for 1 minute. Each item of detection data of the printing finished product is as follows:
comparative example 1
The hydrophilic red color component-1 in the preparation of the liquid red dye composition of example 1 was replaced with a hydrophilic dye having a structure of 23.15g or less,
and 664.91g of water are added to a dispersion tank, and after the dispersion is stirred to be fully dissolved, 311.94g of a dye having the following structure is added thereto:
starting the dispersing machine, dispersing at high speed for 15min, regulating the pH value to 5.5 by ammonia water, continuously dispersing for 2 hours, and then pumping the dispersion slurry into a horizontal sand mill for circularly grinding for 4 hours to obtain the red pasty disperse dye composition 1-1, 1000g, wherein the fineness d50=3.2 mu m and the pH value=5.1.
Taking 1-1 g and 30g of the red advertising disperse dye composition, adding 270g of water for dilution, and continuously grinding for 20 hours to obtain 1-2 g and 300g of red pasty disperse dye composition with fineness d50=0.65 μm and pH=5.2.
According to the requirements of GB/T2374-2007 dye dyeing measurement, the red dye composition 1-2 prepared by the method is adopted for flat screen printing, and the printing process comprises the following steps: textile, printing, drying, baking, finishing and printing to obtain a finished product, wherein: the baking temperature was 100℃for 10 minutes and the baking temperature was 200℃for 1 minute. Each item of detection data of the printing finished product is as follows:
as can be seen from the above examples and comparative examples, the fastness properties of the dye obtained after dyeing are similar to those of the main body conventional disperse dye, but since the hydrophilic dye adopted in comparative example 1 has ionic groups, the hydrophilic dye is partially adsorbed on the surface of the hydrophobic dye, which is helpful for improving the hydrophilicity of hydrophobic red-1 (C.I. disperse red 167), but the overall dispersing ability is weaker, the viscosity is higher in the processing process, and the particle size of the dye is many times larger than that of the final liquid dye product obtained in example 1 under the same grinding time condition.
The hydrophilic dye adopted in the comparison 1 has ionic groups, but can not be converted into hydrophobic groups in the use process, has no property of hydrophilic before hydrophobic, has no affinity with hydrophobic fibers, has larger influence on fastness in the whole dye application process, and is not suitable for being used as a dye for hydrophobic printing and dyeing application.
It can be seen from the comparative examples that not all red hydrophilic dyes except the hydrophilic red dye component described in the patent claims are suitable for use in a similar application to the present patent.
The liquid disperse dye composition prepared in each example in examples 1-15 has excellent fastness performance after dyeing and printing application, is more than grade 4, and is suitable for printing and dyeing application of hydrophobic fabric with high fastness requirements.
Claims (7)
1. A red liquid dye composition for printing is characterized in that: the composition consists of 15-60% of hydrophobic dye monomer, 0.05% -5% of hydrophilic dye monomer and 35% -84.5% of water according to weight percentage;
the hydrophobic dye monomer is one or more of disperse dyes in the formula (I);
formula (I)
R1 is selected from-Cl or-CN;
r2 is selected from-H, -NHCOCH 3 or-NHCOCH 2 CH 3 ；
R3 and R4 may be the same or different and are selected from-CH 2 CH 3 、-CH 2 CH 2 CN、-CH 2 CH 2 OCOCH 3 ；
The hydrophilic dye monomer is one or more of azo compounds containing carboxymethyl sulfonyl shown in a formula (II);
formula (II)
R5 and R6 can be the same or different and are selected from-H or halogen;
r7 is selected from-H or-OCH 3 ；
R8 is selected from the group consisting of-NHCOCH 3 、-NHCOCH 2 CH 3 or-NHCOC 6 H 5 ；
R9 and R10 may be the same or different and are selected from-CH 2 CH 3 、-CH=CHCH 3 or-CH 2 CH 2 OCOCH 3 ；
The water is one or more of tap water, deionized water, distilled water, high-purity water and ultrapure water.
2. A process for the preparation of a red liquid dye composition for printing according to claim 1, wherein: the dye composition can be obtained by blending during the independent preparation and refinement processing.
3. A process for preparing a dye composition according to claim 2, characterized in that: the independent preparation refinement processing is to mix the hydrophobic dye monomer and the hydrophilic dye monomer together in a physical mixing way, and obtain the uniform and stable liquid suspension disperse dye composition with the particle size less than 1 micron through dispersion grinding.
4. Use of a dye composition according to claim 1, characterized in that: the dye composition is applied to a printing process.
5. Use of a dye composition according to claim 4, characterized in that: the technical process comprises the steps of sequentially printing, drying, color development and finishing the textile to be treated, so as to obtain a printed finished product.
6. Use of a dye composition according to claim 5, characterized in that: washing and drying are carried out between the color development and the finishing process; the color development temperature is 160-210 ℃; the color development time is 1-30 minutes; the color development adopts a steaming or baking mode; the washing adopts a mode of multiple times of washing and/or soaping.
7. Use of a dye composition according to claim 4, characterized in that: the dye composition is applied to a printing process, and the specific process is selected from one of the following processes: textile, printing, drying, steaming, water washing, soaping, water washing, drying, finishing and printing to obtain a finished product; textile, printing, drying, steaming, water washing, drying, finishing and printing to obtain a finished product; textile, printing, drying, steaming, drying, finishing and printing finished products; textile, printing, drying, baking, water washing, soaping, water washing, drying, finishing and printing to obtain a finished product; textile, printing, drying, baking, water washing, drying, finishing and printing finished products; textile, printing, drying, baking, finishing and printing to obtain a finished product.
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| CN1289803A (en) * | 2000-10-25 | 2001-04-04 | 大连理工大学 | Temporarily water-soluble disperse dye containing carboxymethyl sulfonyl and its synthesis process |
| CN1401709A (en) * | 2002-09-27 | 2003-03-12 | 大连理工大学 | Ink for waterproof ink-jet printing, spray drawing and ink-jet printing of fabric |
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