CN116715979A - High-performance ink-jet printing reactive red dye and preparation method and application thereof - Google Patents

High-performance ink-jet printing reactive red dye and preparation method and application thereof Download PDF

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Publication number
CN116715979A
CN116715979A CN202310359260.7A CN202310359260A CN116715979A CN 116715979 A CN116715979 A CN 116715979A CN 202310359260 A CN202310359260 A CN 202310359260A CN 116715979 A CN116715979 A CN 116715979A
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Prior art keywords
compound
solution
reactive red
red dye
reaction
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Inventor
刘国成
肖卫国
刘建中
唐炬
吴峰
张卫平
苏金奇
丁扣华
吴李波
王建
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Taixing Jinyun Dye Co ltd
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Taixing Jinyun Dye Co ltd
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Priority to CN202310359260.7A priority Critical patent/CN116715979A/en
Publication of CN116715979A publication Critical patent/CN116715979A/en
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    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/09—Disazo or polyazo 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
    • C09B67/0072—Preparations with anionic dyes or 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0079—Azoic dyestuff preparations
    • 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
    • D06P1/382—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 reactive group directly attached to heterocyclic group
    • 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
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

The invention relates to a high-performance ink-jet printing reactive red dye, and a preparation method and application thereof, and belongs to the field of fine chemical industry. The reactive red dye shown in the formula (I) has higher solubility, high fixation rate and color fastness, high stability after dyeing and bright color, can be widely applied to dip dyeing, pad dyeing and ink-jet printing of cotton, hemp and artificial cotton fiber fabrics, has low production cost and can be popularized and applied on a large scale.

Description

High-performance ink-jet printing reactive red dye and preparation method and application thereof
Technical Field
The invention belongs to the field of fine chemical industry, and particularly relates to a high-performance ink-jet printing reactive red dye, a preparation method thereof and application thereof in dyeing and printing of wool, brocade and cotton fibers.
Background
With the improvement of the application rate, the market demand of the reactive dye is larger and larger, and the market demand of the reactive dye is also improved. Therefore, in order to meet the market demand, the reactive dye is further improved in the aspects of fixation rate, solubility, light fastness, rubbing fastness and the like. At present, the solubility of the common reactive dye in the market can not meet the requirement of ink-jet printing; in addition, the actual utilization rate is not high in the dyeing process, and a large part of the dye is hydrolyzed; in addition, in the traditional medium-high temperature dyeing, the dyeing water consumption is high, the energy consumption is high, and a large amount of salt is needed for auxiliary dyeing. Therefore, high-solubility, high-activity and low-salt green and environment-friendly reactive dyes are the main stream of current research and development.
Disclosure of Invention
The invention aims to provide an ink-jet printing reactive red dye based on the prior art, which does not need to be used in combination with other dyes, has higher solubility, fixation rate and color fastness, high stability after dyeing and bright color, can be widely applied to dip dyeing, pad dyeing and ink-jet printing of cotton, hemp and artificial cotton fabrics, has low production cost and can be popularized and applied on a large scale.
The invention also aims to provide a preparation method of the reactive red dye.
A third object of the present invention is to provide the use of the reactive red dye described above in the dyeing and finishing of fabrics.
The technical scheme of the invention is as follows:
a reactive red dye of formula (I),
wherein R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Independently represent H, -SO 3 M、-NHCH 2 SO 3 M or-SO 2 C 2 H 4 OSO 3 M; m is H or an alkali metal ion.
In a preferred embodiment, R 1 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, further R 1 represents-SO 3 M。
In a preferred embodiment, R 2 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, further R 2 represents-SO 3 M。
In a preferred embodiment, R 3 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, further R 3 represents-SO 3 M。
In a preferred embodiment, R 4 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, further R 4 represents-SO 3 M。
In a preferred embodiment, R 5 Represents H or-SO 3 M。
In a preferred embodiment, R 6 Represents H or-SO 3 M。
In a preferred embodiment, M is H, na or K, preferably M is Na.
For the purposes of the present invention, the reactive red dye of formula I may be selected from the following compounds:
according to the invention, the naphthalene ring structure is directly introduced into the main ring structure of the dye compound, so that the solubility, diffusion speed, fixation rate and stability of a dye product in hard water can be improved, the viscosity of a dye liquor can be reduced, the dye liquor does not need to be combined with other dyes, the use of auxiliary agents is reduced, and the printing and dyeing cost is reduced.
The invention also provides a preparation method of the reactive red dye shown in the formula (I), which comprises the following steps:
wherein M is H or an alkali metal ion.
In a preferred embodiment, the preparation method of the reactive red dye shown in the formula (I) comprises the following steps:
(1) Primary condensation reaction: dissolving the compound 2 in an alkaline solution, regulating the pH value to 5.5-7.0, adding the compound 3, and carrying out a primary condensation reaction at the temperature of 0-5 ℃ to prepare a compound 4, so as to obtain a primary condensation solution;
(2) Primary diazotization reaction: dispersing the compound 5 in water, adding hydrochloric acid, uniformly mixing, regulating the temperature of the obtained mixed solution to 0-5 ℃, adding sodium nitrite, and carrying out diazotization reaction under the condition of keeping the temperature at 0-5 ℃ to obtain diazonium solution;
(3) Primary coupling reaction: uniformly mixing the diazonium solution obtained in the step (2) with the primary condensation solution obtained in the step (1), regulating the pH value to 6.0-7.0, and carrying out coupling reaction at the temperature of 10-15 ℃ to prepare a compound 6, so as to obtain a coupling reaction solution;
(4) Secondary condensation reaction: adding the compound 2 into the coupling reaction liquid obtained in the step (3), regulating the pH value to 5.5-6.5, and carrying out a secondary condensation reaction at the temperature of 40-55 ℃ to prepare a compound 7, so as to obtain a secondary condensation liquid;
(5) Secondary diazotization reaction: dispersing the compound 8 in water, adding hydrochloric acid, uniformly mixing, regulating the temperature of the obtained mixed solution to 0-5 ℃, adding sodium nitrite, and carrying out diazotization reaction under the condition of keeping the temperature at 0-5 ℃ to obtain diazonium solution;
(6) Secondary coupling reaction: uniformly mixing the diazonium solution obtained in the step (5) with the secondary condensation solution obtained in the step (4), regulating the pH value to 6.5-7.5, and carrying out secondary coupling reaction at the temperature of 15-20 ℃ to obtain a dye finished product solution;
(7) And (3) drying: and (3) spray drying the dye finished product solution obtained in the step (6) to obtain the reactive red dye shown in the formula (I).
The invention can adjust the pH value of the solution by adopting proper acid, alkali or salt (such as hydrochloric acid and sodium carbonate) according to the requirement. In a preferred embodiment, in step (3) or step (6), sodium bicarbonate is added to adjust the pH during the coupling reaction; in the step (4), sodium bicarbonate is added to adjust the pH value during the secondary condensation reaction.
In a preferred embodiment, in step (1), the alkaline solution is sodium hydroxide solution or sodium bicarbonate solution during the primary condensation reaction.
In a preferred embodiment, in step (7), the finished dye solution is spray dried in a spray drying tower.
A dye composition takes the active red dye as an active component and is assisted with an auxiliary agent in the dye field. For example, the auxiliary agent is one or more of dust-proof agent, filler and anhydrous sodium sulfate. The dye finished product prepared by the reactive red dye can exist in solid particles, powder or solution. The reactive component may include only one of the above reactive red dyes, or may include two or more reactive red dyes. Adjuvants in the dye arts include, but are not limited to, co-solvents, dust-proofing agents (e.g., polyoxyethylene ether oleate mixtures), fillers, anhydrous sodium sulfate, stabilizers or electrolyte salts, etc., which are common in commercial dyes, such as sodium chloride, potassium chloride, sodium sulfate or potassium sulfate.
The reactive red dye disclosed by the invention can be applied to textile printing and dyeing, in particular to dip dyeing, pad dyeing or ink-jet printing of cotton, hemp or artificial cotton fibers.
By adopting the technical scheme of the invention, the advantages are as follows:
(1) The ink-jet printing reactive red dye has high solubility which can reach 400g/L based on the existence of the water-soluble group.
(2) The high solubility and high level dyeing property of the ink-jet printing reactive red dye enable the dye to be full in dyeing color and luster, and the lifting force and the dyeing depth are further improved.
(3) According to the invention, the naphthalene ring structure is directly introduced into the main ring structure of the dye compound, and the dye compound modified by the naphthalene ring further improves the solubility and diffusion speed of the reactive dye, reduces the viscosity of the dye liquor, and improves the adaptability and stability of hard water of the product; and the fiber can be properly softened, so that the softness of the printing fabric is improved.
(4) The preparation method of the dye is optimized, and the synthesis steps of primary condensation, diazo coupling, secondary condensation and diazo coupling are adopted, so that the hydrolysis side reaction in the processing process of the dye product is reduced, the pH value of the dye product is prevented from being reduced, and the stability and yield of the finished dye are improved.
(5) The drying mode is optimized, the original salting-out and filter cake drying modes are replaced by direct spray drying, no sewage is discharged, and the dried product obtained by drying can be directly packaged, so that the environmental pollution is avoided, and the production cost is saved.
(6) The reactive red dye provided by the invention is combined with the wool, brocade and cotton fibers by covalent bonds, and the covalent bonds are quite firm, so that the dye has high color fastness.
In conclusion, the reactive red dye provided by the invention is bright and beautiful, does not need to be compounded with other dyes for use, has high solubility, high fixation rate, excellent wet rubbing fastness, easy cleaning and the like; meanwhile, the product obtained by spray drying by adopting the spray drying tower can be directly packaged, no sewage is discharged, the environmental pollution is avoided, and the production cost is saved.
Detailed Description
The red dyes of the present invention are further illustrated by the following examples, which are not intended to limit the invention in any way.
Example 1
(1) Primary condensation reaction: 184.5 parts of cyanuric chloride (compound 3) are subjected to an ice mill; 319.3 parts of H acid (Compound 2) are dissolved in NaHCO 3 In solution, add NaHCO 3 And (3) regulating the pH value to 5.5-7.0, adding cyanuric chloride (compound 3) subjected to ice grinding treatment, controlling the temperature to 0-5 ℃ in the process of primary condensation reaction, reacting for 2-4 hours, preparing compound 4, detecting by HPLC, and obtaining primary condensation liquid after H acid disappears.
(2) Diazotization reaction: dispersing the compound 5 in water, adding 51.1 parts of hydrochloric acid, uniformly mixing, regulating the temperature of the mixed solution to 0-5 ℃, adding 69.7 parts of sodium nitrite into the mixed solution for 30-40 minutes, maintaining the temperature at 0-5 ℃, reacting for 2 hours, and obtaining the diazonium solution containing the compound 5 after the test of the starch potassium iodide test paper shows colorless and the test of the Congo red test paper shows blue.
(3) Coupling reaction: adding the diazonium solution containing the compound 5 obtained in the step (2) to the primary condensation solution obtained in the step (1), and using NaHCO 3 The pH value is regulated to 6.0-7.0, the temperature is controlled to be 10-15 ℃, and the reaction is carried out for 2-4 hours, so as to prepare the compound 6, and the coupling reaction liquid is obtained.
(4) Secondary condensation reaction: 319.3 parts of H acid (Compound 2) were added to the coupling reaction solution obtained in step (3), with NaHCO 3 Adjusting the pH value to 5.5-6.5, heating to 40-45 ℃ at the same time, and reacting for 5-6 hours to prepare a compound 7, thus obtaining a secondary condensation solution for later use;
(5) Secondary diazotization reaction: 223.3 parts of diazonium solution containing a compound 8 (the structural formula of the compound 8 is the same as that of the compound 5) is dispersed in water, 51.1 parts of hydrochloric acid is added, after uniform mixing, the temperature of the mixed solution is regulated to 0-5 ℃, 69.7 parts of sodium nitrite is added into the mixed solution for 30-40 minutes, the temperature is maintained at 0-5 ℃ for 2 hours, and after the reaction, the solution is subjected to a reaction for 2 hours, a test of starch potassium iodide test paper shows colorless, a test of Congo red test paper shows blue, and the diazonium solution containing the compound 8 is obtained.
(6) Secondary coupling reaction: adding the diazonium solution containing the compound 8 obtained in the step (5) to the secondary condensation solution obtained in the step (4), and using NaHCO 3 Adjusting the pH value to 6.5-7.5, heating to 15-20 ℃ at the same time, reacting for 4-5 hours to obtain dye finished product solution,
(7) And (3) drying: and (3) spray drying the dye finished product solution obtained in the step (6) in a spray drying tower to obtain the compound shown in the formula (1-1).
The structural formula of the related compound is as follows:
wherein mass spectrum data of the compound (I-1) are as follows: MS (EI, m/z): 1553.51[ M-H ]] - 。
Example 2
Referring to the preparation method in example 1, in step (2) and step (5), diazotization was performed using the following compound (compound 8 has the same structural formula as compound 5) instead of compound 5 in example 1, respectively, to obtain the compound represented by formula (I-2). The structural formula of the related compound is as follows:
wherein mass spectrum data of the compound (I-2) are as follows: MS (EI, m/z): 1757.59[ M-H ] -.
The dye disclosed in comparative example 1 CN104292881a has the following structural formula:
the dye disclosed in comparative example 2 patent CN104292881a has the following structural formula:
description of printing and dyeing experiments
100 parts of the compound dyes of examples 1 to 5, comparative example 1 and comparative example 2 were respectively sprinkled into 100 parts of raw stock containing 50 parts of 5% sodium alginate thickener, 27.8 parts of water, 20 parts of urea, 1 part of sodium m-nitrobenzenesulfonate and 1.2 parts of sodium bicarbonate, cotton fabrics were printed with the thus-prepared printing paste and dried, and the printed fabrics were steamed with 100-102 ℃ saturated steam for 2 minutes, then rinsed, if necessary, soaped at boiling, rinsed again and dried. The sample properties of the examples and comparative examples were examined according to the national dye unification test standards, respectively, and the results are shown in table 1.
Table 1 results of examples and comparative examples performance printing tests
Examples and comparative examples performance test methods national dye unification test standards were performed as follows.
As can be seen from the printing and dyeing test results in Table 1, the reactive red dye for ink-jet printing disclosed in examples 1-2 of the present invention is excellent in terms of rubbing fastness, light fastness, washing fastness, solubility, alkali-resistant stability, and fixation rate, particularly in terms of solubility and fixation rate. Other inkjet printing reactive red dyes disclosed herein, such as the compounds shown in (1-1) or the compounds shown in (1-2), all have similar effects.
Compared with the dyes disclosed in comparative examples 1 and 2, the reactive red dye for ink-jet printing disclosed by the invention has better performances in the aspects of rubbing fastness, light fastness, washing fastness, solubility, alkali resistance stability and fixation rate.
The above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments may be modified or some technical features may be replaced equivalently; such modifications and substitutions do not depart from the spirit of the invention.

Claims (10)

1. Has a reactive red dye shown in a formula (I),
wherein R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Independently represent H, -SO 3 M、-NHCH 2 SO 3 M or-SO 2 C 2 H 4 OSO 3 M; m is H or an alkali metal ion.
2. The reactive red dye according to claim 1, wherein R 1 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, preferably R 1 represents-SO 3 M；R 3 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, preferably R 3 represents-SO 3 M；
R 5 Represents H or-SO 3 M。
3. The reactive red dye according to claim 1, wherein R 2 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, preferably R 2 represents-SO 3 M；R 4 represents-SO 3 M or-SO 2 C 2 H 4 OSO 3 M, preferably R 4 represents-SO 3 M；
R 6 Represents H or-SO 3 M。
4. The reactive red dye according to claim 1, wherein M is H, na or K.
5. The reactive red dye according to claim 1, characterized in that the dye is selected from the following compounds:
6. a process for the preparation of a reactive red dye according to claim 1, comprising the steps of:
wherein M is H or an alkali metal ion.
7. The method for preparing the reactive red dye according to claim 6, which comprises the following steps:
(1) Primary condensation reaction: dissolving the compound 2 in an alkaline solution, regulating the pH value to 5.5-7.0, adding the compound 3, and carrying out a primary condensation reaction at the temperature of 0-5 ℃ to prepare a compound 4, so as to obtain a primary condensation solution;
(2) Primary diazotization reaction: dispersing the compound 5 in water, adding hydrochloric acid, uniformly mixing, regulating the temperature of the obtained mixed solution to 0-5 ℃, adding sodium nitrite, and carrying out diazotization reaction under the condition of keeping the temperature at 0-5 ℃ to obtain diazonium solution;
(3) Primary coupling reaction: uniformly mixing the diazonium solution obtained in the step (2) with the primary condensation solution obtained in the step (1), regulating the pH value to 6.0-7.0, and carrying out coupling reaction at the temperature of 10-15 ℃ to prepare a compound 6, so as to obtain a coupling reaction solution;
(4) Secondary condensation reaction: adding the compound 2 into the coupling reaction liquid obtained in the step (3), regulating the pH value to 5.5-6.5, and carrying out a secondary condensation reaction at the temperature of 40-55 ℃ to prepare a compound 7, so as to obtain a secondary condensation liquid;
(5) Secondary diazotization reaction: dispersing the compound 8 in water, adding hydrochloric acid, uniformly mixing, regulating the temperature of the obtained mixed solution to 0-5 ℃, adding sodium nitrite, and carrying out diazotization reaction under the condition of keeping the temperature at 0-5 ℃ to obtain diazonium solution;
(6) Secondary coupling reaction: uniformly mixing the diazonium solution obtained in the step (5) with the secondary condensation solution obtained in the step (4), regulating the pH value to 6.5-7.5, and carrying out secondary coupling reaction at the temperature of 15-20 ℃ to obtain a dye finished product solution;
(7) And (3) drying: and (3) spray drying the dye finished product solution obtained in the step (6) to obtain the reactive red dye shown in the formula (I).
8. The method for preparing a reactive red dye according to claim 7, wherein in the step (1), the alkaline solution is sodium hydroxide solution or sodium bicarbonate solution during a condensation reaction; in the step (3) or the step (6), sodium bicarbonate is added to adjust the pH value of the reaction mixture in the coupling reaction process; in the step (4), sodium bicarbonate is added to adjust the pH value of the solution in the process of the secondary condensation reaction; the weight ratio of the compound 2 to the compound 3 to the compound 5 to the compound 8 to the hydrochloric acid to the sodium nitrite is 1:0.2-0.4:0.2-0.6:0.2-0.6:0.1-0.3:0.1-0.4, preferably 1:0.3:0.35:0.35:0.16:0.22.
9. A dye composition, which takes the active red dye as an active component and is assisted by an auxiliary agent in the dye field, wherein the auxiliary agent is one or more of a dustproof agent, a filler and anhydrous sodium sulphate.
10. Use of the reactive red dye according to any one of claims 1 to 5 for dyeing and printing textiles; in particular in dip dyeing, pad dyeing or inkjet printing of cotton, hemp or rayon fibers.
CN202310359260.7A 2023-04-06 2023-04-06 High-performance ink-jet printing reactive red dye and preparation method and application thereof Pending CN116715979A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2748965A1 (en) * 1977-11-02 1979-05-03 Hoechst Ag HYDRO-SOLUBLE COLORS, PROCESS FOR THEIR PRODUCTION, THEIR USE AS FIBER-REACTIVE COLORS FOR COLORING AND PRINTING FIBER MATERIALS AND FIBER MATERIALS DYED WITH THEM
JPS61195176A (en) * 1985-02-26 1986-08-29 Ricoh Co Ltd Aqueous ink composition
DE4413007A1 (en) * 1994-04-15 1995-10-19 Bayer Ag New dyes and their use in inks for ink-jet printing processes
CN1112947A (en) * 1994-05-02 1995-12-06 赫彻斯特股份公司 Mixtures of fiber-reactive dyes and use thereof for dyeing fiber materials

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2748965A1 (en) * 1977-11-02 1979-05-03 Hoechst Ag HYDRO-SOLUBLE COLORS, PROCESS FOR THEIR PRODUCTION, THEIR USE AS FIBER-REACTIVE COLORS FOR COLORING AND PRINTING FIBER MATERIALS AND FIBER MATERIALS DYED WITH THEM
JPS61195176A (en) * 1985-02-26 1986-08-29 Ricoh Co Ltd Aqueous ink composition
US4647310A (en) * 1985-02-26 1987-03-03 Ricoh Company, Ltd. Aqueous ink composition for ink jet-recording
DE4413007A1 (en) * 1994-04-15 1995-10-19 Bayer Ag New dyes and their use in inks for ink-jet printing processes
CN1112947A (en) * 1994-05-02 1995-12-06 赫彻斯特股份公司 Mixtures of fiber-reactive dyes and use thereof for dyeing fiber materials

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