CN103044959B - Reactive red dye suitable for nylon dyeing - Google Patents
Reactive red dye suitable for nylon dyeing Download PDFInfo
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- CN103044959B CN103044959B CN201010266030.9A CN201010266030A CN103044959B CN 103044959 B CN103044959 B CN 103044959B CN 201010266030 A CN201010266030 A CN 201010266030A CN 103044959 B CN103044959 B CN 103044959B
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Abstract
The invention relates to a reactive red dye suitable for nylon dyeing. The dye is a compound as shown in a formula (I). A preparation method comprises: a, adding an ethanolamine acetate solution into a cyanuric chloride solution to react to obtain a first condensation liquid, and adding a J acid into the first condensation liquid to obtain a second condensation liquid; b, adding a hydrochloric acid solution and a sodium nitrite solution into p-aminoazobenzene, reacting under a pH of less than 2, and eliminating excess nitrous acid with sulfamic acid to obtain a diazo liquid; c, dropwise adding the diazo liquid obtained in the step b into the second condensation liquid obtained in the step a to obtain a coupling reaction solution; d, heating the coupling reaction solution obtained in the step c, and hydrolyzing under a pH of 8-11; e, filtering the hydrolysis reaction solution obtained in the step d to remove slag, and collecting filtrate; f, adjusting colored light and intensity of the filtrate obtained in the step e; and g, performing a spray drying for the color liquid of the step f to obtain the finish product of the formula (I).
Description
Technical field
The present invention relates to a kind of preparation method of nylon reactive dye.Especially nylon red reactive dyes and preparation method thereof.
Background technology
The present general nylon dyestuff used that dyes is matching stain, weak acid dye and metallized dye.The every wet fastness of nylon contaminated due to these dyestuffs is not good enough, and coloured light is not very gorgeous, and the low rate of clean absorption rate, dyeing liquid waste concentration is high, and particularly heavy metal, causes severe contamination to environment.Enter 21 century, due to the restriction of environmental ecology, for dye uptake, the requirement of degree of fixation and dyeing waste liquid is more and more higher.Matching stain, weak acid dye and metal complex, can not meet dyeing nylon demand.
Current urgent need reduce environmental pollution and also raw materials cost low, beautiful in colour, the excellent nylon reactive red dye of every wet fastness properties.
Summary of the invention
In order to solve the problems of the technologies described above, the invention provides a kind of red nylon reactive dye and preparation method thereof, this dyestuff is for as shown in the formula the compound shown in (I):
Wherein: M is-H or basic metal, preferred as alkali is Na or K.
The preparation method of the dye composition of above-mentioned formula (I) comprises the steps:
A, condensation reaction:
Thanomin acetic ester solution joins reaction in cyanuric chloride solution and obtains primary condensation liquid, then in this condensated liquid, adds J acid, obtains secondary condensation liquid;
B, diazotization reaction:
In P-aminoazobenzene, add hydrochloric acid soln and sodium nitrite solution, react when PH < 2, then eliminate excessive nitrite with thionamic acid, obtain diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensation liquid of a step, obtains coupled reaction liquid;
D, hydrolysis reaction:
Step c coupled reaction liquid is heated up, keeps pH=8-11 hydrolysis;
E, removal insolubles:
Step d hydrolysis reaction liquid is filtered and removes waste residue, collect filtrate;
F, adjustment coloured light and intensity:
Step e filtrate is carried out coloured light, intensity adjustment;
G, drying:
The look liquid of f step is carried out spraying dry, obtains formula (I) the finished product.
Preferably, the preparation method of the dye composition of above-mentioned formula (I) comprises the steps:
A, condensation reaction:
The thanomin acetic ester solution of pH=2-5 is joined in cyanuric chloride solution, keeps T=0-15 DEG C, pH=2-3.5, reaction 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, add J acid, adjustment T=15-40 DEG C, pH=4-6, reaction 2-4 hour, obtains secondary condensation liquid;
B, diazotization reaction:
In low temperature P-aminoazobenzene, add hydrochloric acid soln and sodium nitrite solution, at T=0-20 DEG C, PH < 2, reaction 1-3 hour, eliminates excessive nitrite with thionamic acid, obtains diazo liquid;
C, coupled reaction:
Be added drop-wise in the secondary condensation liquid of a step by b step gained diazo liquid, keep T=10-20 DEG C, pH=5-7, reaction 1-2 hour, obtains coupled reaction liquid;
D, hydrolysis reaction:
Step c coupled reaction liquid is warming up to 30-50 DEG C, keeps pH=8-11, reaction 5-7 hour;
E, removal insolubles:
Step d hydrolysis reaction liquid is joined in solid-liquid separator, is separated, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of step e filtrate, then carry out coloured light, intensity adjustment according to coloration result;
G, drying:
Join in feed liquid preheater by the look liquid of f step, adjustment inlet temperature and temperature out carry out spraying dry, obtain formula (I) the finished product.
Preferably, the preparation method of the dye composition of above-mentioned formula (I) comprises the steps:
A, condensation reaction:
In dissolving vessel, add water of a small amount of end and thanomin acetic ester, use NaHCO
3be neutralized to pH=2-5, obtain thanomin acetic ester solution; In a kettle., add a small amount of water and a small amount of trash ice, then add cyanuric chloride, in stirring, drip thanomin acetic ester solution, T=0-15 DEG C, pH=2-3.5, dropwises, reaction 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, J acid is added, adjustment T=15-40 DEG C, pH=4-6, reaction 2-4 hour, obtains secondary condensation liquid;
B, diazotization reaction:
Add end water and P-aminoazobenzene in a kettle., stir, add trash ice and 30% hydrochloric acid soln and sodium nitrite solution, at T=0-20 DEG C, PH < 2, reaction 1-3 hour, eliminate excessive nitrite with thionamic acid, obtain diazo liquid;
C, coupled reaction:
Be added drop-wise in the secondary condensation liquid of a step by b step gained diazo liquid, T=10-20 DEG C in dropping process, adjusts pH=5-7 with soda ash, drips and finishes, and reaction 1-2 hour, obtains coupled reaction liquid;
D, hydrolysis reaction:
Step c coupled reaction liquid is warming up to 30-50 DEG C, keeps pH=8-11 with soda ash, reaction 5-7 hour;
E, removal insolubles:
Step d hydrolysis reaction liquid is joined in solid-liquid separator, is separated, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of step e filtrate, then carry out coloured light, intensity adjustment according to coloration result;
G, drying:
Join in feed liquid preheater by the look liquid of f step, adjustment inlet temperature 210 DEG C, carries out spraying dry with the temperature out of 95-100 DEG C, obtains formula (I) the finished product.
In aforesaid method, preferably, T=5-10 DEG C in the preparation of primary condensation liquid, the reaction times is 5 hours;
In aforesaid method, preferably, T=20-30 DEG C in the preparation of secondary condensation liquid, the reaction times is 3 hours;
In aforesaid method, preferably, T=5-15 DEG C in diazotization reaction, the reaction times is 2 hours;
Wherein the structure of thanomin acetic ester is as follows:
H
2NCH
2CH
2OCOCH
3
The structure of cyanuric chloride is as follows:
The structure of J acid is as follows:
The structure of P-aminoazobenzene is as follows:
Intermediate used in aforesaid method is all known compound disclosed in prior art, all can commercially obtain by gum.
In aforesaid method, what T represented is temperature, such as T=10-20 DEG C, represents that temperature is between 10-20 DEG C.
Present invention also offers a kind of composition for dyeing nylon, the dye composition of said composition contained (I) and dyestuff carrier.
The dye composition that present invention also offers above-mentioned formula (I) is used for the purposes of dyeing nylon.
Preparation and the use of the dyestuff of above-mentioned formula (I) compound can reduce environmental pollution, particularly reduce the pollution of heavy metal.And desired raw material cost is low, beautiful in colour, every wet fastness, such as wetly to rub, soap, alkali sweat, sour sweat, the excellent performance such as washing, easy to use, be the excellent nylon reactive red dye being applicable to dyeing nylon.
Embodiment
The preparation of the nylon reactive red dye compound of embodiment 1 structural formula (II)
The preparation of a, condenses:
In dissolving vessel, add water of a small amount of end and thanomin acetic ester 22Kg, use NaHCO
3in and pH=4-5, obtain thanomin acetic ester solution; In a kettle., add a small amount of water and a small amount of trash ice, then add cyanuric chloride 19Kg, in stirring, drip thanomin acetic ester, T=10-15 DEG C, pH=2-3.5, dropwise, and reacts 5 hours, obtain primary condensation liquid; In primary condensation liquid, add J acid 26.5Kg, adjustment T=35-40 DEG C, pH=5-6, react 3 hours, obtain secondary condensation liquid.
B, P-aminoazobenzene diazotization:
Add end water, P-aminoazobenzene 23.2Kg in a kettle., stir, add trash ice, 30% hydrochloric acid soln and sodium nitrite solution.At 15-20 DEG C, PH < 2, react 2 hours, (in micro-blueness after starch potassium iodide paper leaching), eliminates excessive nitrite with thionamic acid, obtains diazo liquid.
C, coupled reaction:
Diazo liquid b step obtained is added drop-wise in a step secondary condensated liquid, drips process T=15-20 DEG C, adjusts pH=5-7 with soda ash, drips and finishes, react 2 hours, obtain coupled reaction liquid.
D, hydrolysis reaction:
Step c coupled reaction liquid is warming up to 45-50 DEG C, keeps pH=10-11 with soda ash, react 6 hours.
E, removal insolubles:
Step d hydrolysis reaction liquid is joined in solid-liquid separator, is separated, remove waste residue, collect filtrate in storage tank.
F, adjustment coloured light and intensity:
Step e material is dyeed, then carries out coloured light, intensity adjustment according to coloration result
G, drying:
Join in feed liquid preheater by the look liquid of f step, adjustment inlet temperature 210 DEG C, carries out spraying dry with the temperature out of 95-100 DEG C, obtains the finished product 107Kg.
The application performance table of the nylon reactive red dye of the formula (II) of embodiment 1
The preparation method of dyestuff of the present invention and dyestuff thereof is described by specific embodiment.Those skilled in the art can use for reference the links such as content appropriate change raw material of the present invention, processing condition and realize other object corresponding, its relevant change does not all depart from content of the present invention, all similar replacements and change will become apparent to those skilled in the art that and be all deemed to be included within scope of the present invention.
Claims (8)
1. a red nylon reactive dye, this dyestuff is the compound shown in following formula I:
Wherein: M is-H or basic metal.
2. a kind of red nylon reactive dye according to claim 1, is characterized in that: described basic metal is Na or K.
3. the preparation method of dyestuff according to claim 1, the method comprises the steps:
A, condensation reaction:
Thanomin acetic ester solution joins reaction in cyanuric chloride solution and obtains primary condensation liquid, then in this condensated liquid, adds J acid, obtains secondary condensation liquid;
B, diazotization reaction:
In P-aminoazobenzene, add hydrochloric acid soln and sodium nitrite solution, react when pH < 2, then eliminate excessive nitrite with thionamic acid, obtain diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensation liquid of a step, obtains coupled reaction liquid;
D, hydrolysis reaction:
Step c coupled reaction liquid is heated up, keeps pH=8-11 hydrolysis;
E, removal insolubles:
Step d hydrolysis reaction liquid is filtered and removes waste residue, collect filtrate;
F, adjustment coloured light and intensity:
Step e filtrate is carried out coloured light, intensity adjustment;
G, drying:
The look liquid of f step is carried out spraying dry, obtains formula (I) the finished product.
4. method according to claim 3, the method comprises the steps:
A, condensation reaction:
The thanomin acetic ester solution of pH=2-5 is joined in cyanuric chloride solution, keeps T=0-15 DEG C, pH=2-3.5, reaction 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, add J acid, adjustment T=15-40 DEG C, pH=4-6, reaction 2-4 hour, obtains secondary condensation liquid;
B, diazotization reaction:
In low temperature P-aminoazobenzene, add hydrochloric acid soln and sodium nitrite solution, at T=0-20 DEG C, pH < 2, reaction 1-3 hour, eliminates excessive nitrite with thionamic acid, obtains diazo liquid;
C, coupled reaction:
Be added drop-wise in the secondary condensation liquid of a step by b step gained diazo liquid, keep T=10-20 DEG C, pH=5-7, reaction 1-2 hour, obtains coupled reaction liquid;
D, hydrolysis reaction:
Step c coupled reaction liquid is warming up to 30-50 DEG C, keeps pH=8-11, reaction 5-7 hour;
E, removal insolubles:
Step d hydrolysis reaction liquid is joined in solid-liquid separator, is separated, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of step e filtrate, then carry out coloured light, intensity adjustment according to coloration result;
G, drying:
Join in feed liquid preheater by the look liquid of f step, adjustment inlet temperature and temperature out carry out spraying dry, obtain formula (I) the finished product.
5. the method according to claim 3 or 4, the method comprises the steps:
A, condensation reaction:
In dissolving vessel, add water of a small amount of end and thanomin acetic ester, use NaHCO
3be neutralized to pH=2-5, obtain thanomin acetic ester solution; In a kettle., add a small amount of water and a small amount of trash ice, then add cyanuric chloride, in stirring, drip thanomin acetic ester solution, T=0-15 DEG C, pH=2-3.5, dropwises, reaction 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, J acid is added, adjustment T=15-40 DEG C, pH=4-6, reaction 2-4 hour, obtains secondary condensation liquid;
B, diazotization reaction:
Add end water and P-aminoazobenzene in a kettle., stir, add trash ice and 30% hydrochloric acid soln and sodium nitrite solution, at T=0-20 DEG C, pH < 2, reaction 1-3 hour, eliminate excessive nitrite with thionamic acid, obtain diazo liquid;
C, coupled reaction:
Be added drop-wise in the secondary condensation liquid of a step by b step gained diazo liquid, T=10-20 DEG C in dropping process, adjusts pH=5-7 with soda ash, drips and finishes, and reaction 1-2 hour, obtains coupled reaction liquid;
D, hydrolysis reaction:
Step c coupled reaction liquid is warming up to 30-50 DEG C, keeps pH=8-11 with soda ash, reaction 5-7 hour;
E, removal insolubles:
Step d hydrolysis reaction liquid is joined in solid-liquid separator, is separated, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of step e filtrate, then carry out coloured light, intensity adjustment according to coloration result;
G, drying:
Join in feed liquid preheater by the look liquid of f step, adjustment inlet temperature 210 DEG C, carries out spraying dry with the temperature out of 95-100 DEG C, obtains formula (I) the finished product.
6. method according to claim 5, wherein T=5-10 DEG C in the preparation of primary condensation liquid, the reaction times is 5 hours.
7. method according to claim 5, wherein T=20-30 DEG C in the preparation of secondary condensation liquid, the reaction times is 3 hours.
8. method according to claim 5, wherein T=5-15 DEG C in diazotization reaction, the reaction times is 2 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010266030.9A CN103044959B (en) | 2010-08-30 | 2010-08-30 | Reactive red dye suitable for nylon dyeing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010266030.9A CN103044959B (en) | 2010-08-30 | 2010-08-30 | Reactive red dye suitable for nylon dyeing |
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| Publication Number | Publication Date |
|---|---|
| CN103044959A CN103044959A (en) | 2013-04-17 |
| CN103044959B true CN103044959B (en) | 2015-02-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010266030.9A Active CN103044959B (en) | 2010-08-30 | 2010-08-30 | Reactive red dye suitable for nylon dyeing |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5149791A (en) * | 1989-11-01 | 1992-09-22 | Ciba-Geigy Corporation | Chlorotriazine reactive dyes having a 4-methoxy-2-sulfoaniline diazo component and 2-amino-5-naphthol-7-sulfonic acid coupling component |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3646409B2 (en) * | 1996-06-17 | 2005-05-11 | 住友化学株式会社 | Bisazo compound and method for dyeing or printing fiber material using the same |
| GB9622912D0 (en) * | 1996-11-04 | 1997-01-08 | Clariant Int Ltd | Organic compounds |
| JP2002322383A (en) * | 2001-04-26 | 2002-11-08 | Sumitomo Chem Co Ltd | Monoazo compound or its salt and their application to fiber material |
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2010
- 2010-08-30 CN CN201010266030.9A patent/CN103044959B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5149791A (en) * | 1989-11-01 | 1992-09-22 | Ciba-Geigy Corporation | Chlorotriazine reactive dyes having a 4-methoxy-2-sulfoaniline diazo component and 2-amino-5-naphthol-7-sulfonic acid coupling component |
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| CN103044959A (en) | 2013-04-17 |
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Address after: 300270 No. 1558 Kaixuan street, Dagang Petrochemical Industrial Park, Binhai New Area, Tianjin Patentee after: Tianjin Dek Chemical Co.,Ltd. Address before: 300163 Tianjin city Dongli District ZhangGuiZhuang road Ji'an Road Patentee before: Tianjin Dek Chemical Co.,Ltd. |
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Effective date of registration: 20230131 Granted publication date: 20150225 |
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