CN102924348A - Reactive dye and intermediate thereof - Google Patents
Reactive dye and intermediate thereof Download PDFInfo
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- CN102924348A CN102924348A CN2012103620825A CN201210362082A CN102924348A CN 102924348 A CN102924348 A CN 102924348A CN 2012103620825 A CN2012103620825 A CN 2012103620825A CN 201210362082 A CN201210362082 A CN 201210362082A CN 102924348 A CN102924348 A CN 102924348A
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- sulfonic acid
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- 239000000985 reactive dye Substances 0.000 title abstract 4
- 239000012048 reactive intermediate Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000004458 analytical method Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 239000013067 intermediate product Substances 0.000 claims description 18
- -1 sulfone sulfate Chemical class 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000010009 beating Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000012954 diazonium Substances 0.000 claims description 6
- 150000001989 diazonium salts Chemical class 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000006277 sulfonation reaction Methods 0.000 claims description 4
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000003931 anilides Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000009413 insulation Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- ASASRSMRAPYLQI-UHFFFAOYSA-N 2-(3-aminophenyl)sulfonylethanol Chemical compound NC1=CC=CC(S(=O)(=O)CCO)=C1 ASASRSMRAPYLQI-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000007613 environmental effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
The invention relates to a reactive dye and an intermediate thereof. The intermediate of the dye is (3-beta-hydroxyethylsulfonyl sulphate) aniline-5-sulfonic acid. The invention also provides a method for preparing the intermediate of the dye and the reactive dye prepared from the intermediate. Compared with the common intermediate of the dye, namely (3-beta-hydroxyethylsulfonyl) aniline, the intermediate of the dye has the advantage that sulfonyl is added, so that the water solubility of the synthesized dye can be improved well. The prepared reactive dye is low in cost of required raw materials, high in solubility, bright in color and high in application performance and applicability, and environmental pollution can be reduced in the preparation process.
Description
Technical field
The present invention relates to the reactive dyestuffs field, particularly a kind of new dyestuff intermediate and the reactive dyestuffs that prepared by this dyestuff intermediate.
Background technology
Present on the market main dyestuff or take matching stain, mordant dyes and metallized dye as main, it is not good enough that the dyestuff of the above-mentioned type dyes the material fastness, coloured light is bright-coloured not, degree of fixation is low, big for environment pollution, particularly the metallized dye free heavy metal that may occur has harm to human body with to environment.Because the restriction of environmental ecology, more and more higher for the requirement that dyestuff dye uptake, degree of fixation and dyeing waste-water are processed, therefore need a kind of high performance dyestuff, the invention provides a kind of reactive dyestuffs, the desired raw material cost is low, and product solubility is high, and bright in colour, application performance is excellent, and suitability is strong, and preparation process can environmental contamination reduction.
As everyone knows, between position oil namely (3-β-hydroxyethyl sulfone) aniline be a kind of important active group intermediate of KN type reactive dyestuffs, the present invention adopts oleum method of sulfonation, with (3-β-hydroxyethyl sulfone) oil of mirbane, introduce a sulfonic group, again by hydrolysis, reduction, esterification, generate i.e. (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid of a kind of new dye activity base intermediate, this structure compared with a position oil how sulfonic group, can well improve synthetic after dyestuff water-soluble, thereby greatly improve the correlated performance of dyestuff.
Summary of the invention
An object of the present invention is to provide a kind of new dyestuff intermediate, this dyestuff intermediate is than dyestuff intermediate (3-β-hydroxyethyl sulfone) aniline commonly used, many sulfonic groups, can improve well synthetic after dyestuff water-soluble, another object of the present invention provides the reactive dyestuffs that made by this new dyestuff intermediate, this reactive dyestuffs desired raw material cost is low, product solubility is high, and bright in colour, and application performance is excellent, suitability is strong, and preparation process can environmental contamination reduction.
The technical solution used in the present invention is:
A kind of dyestuff intermediate, the structural formula of this dyestuff intermediate be as shown in the formula (I):
Name: (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid, molecular formula: C
8H
11NO
9S
3M=361
Another object of the present invention provides the preparation method of above-mentioned dyestuff intermediate (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid, and the method comprises the steps:
1), sulfonation
With (3-β-hydroxyethyl sulfone) oil of mirbane, join in the four-hole bottle that fills chlorsulfonic acid, fully stir in the reinforced process, and with water bath heat preservation below 30 ℃; The reinforced post-heating to 40 ℃-60 ℃ of finishing keeps 1h (at this moment, the complete esterification of β-hydroxyethyl sulfone), reheat 180 ℃, the rear ice that reacts completely is analysed, and adds refined salt, and analysis of material filters and obtains filter cake is the first step intermediate product (3-β-hydroxyl second sulfone sulfate base) oil of mirbane-5-sulphonic acid chloride;
2), hydrolysis
With step 1) gained the first step intermediate product (3-β-hydroxyl second sulfone sulfate base) oil of mirbane-5-sulphonic acid chloride, be dissolved in water, heated solution is to boiling, rear cooling reacts completely, add refined salt, analysis of material filters and obtains second step intermediate product (3-β-hydroxyethyl sulfone) oil of mirbane-5-sulfonic acid;
3), hydrogenating reduction
With step 2) gained second step intermediate product (3-β-hydroxyethyl sulfone) oil of mirbane-5-sulfonic acid is added to the water making beating, put in the autoclave, add the catalyzer Raney's nickel, sealing autoclave displaces the air of the inside to wherein passing into nitrogen, and then pass into hydrogen, be heated to 100 ℃, keep passing into hydrogen pressure 1.2MPa, rear cooling discharge reacts completely, add refined salt, analysis of material filters and obtains the 3rd step intermediate product (3-β-hydroxyethyl sulfone) aniline-5-sulfonic acid;
4), esterification
With step 3) the 3rd step intermediate product (3-β-hydroxyethyl sulfone) aniline-5-sulfonic acid joins in the oleum, and reinforced process water is bathed insulation below 30 ℃; Then be warming up to 60 ℃ of reactions, the rear ice that reacts completely is analysed, and adds refined salt, and the analysis of material filtration obtains filter cake and namely obtains product (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid.
Product analysis
Final product is carried out stratographic analysis, and chromatographic purity adopts its product content of the amino value measuring and calculating of chemistry titration more than 95%, calculates total recovery about 70%.
The reaction principle that above-mentioned steps relates to is as follows:
The present invention also provides above-mentioned dyestuff intermediate (3-β-hydroxyl second sulfone sulfate base) aniline-application of 5-sulfonic acid in preparation of dyestuff.
Another object of the present invention provides a kind of reactive dyestuffs by above-mentioned dyestuff intermediate (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid preparation, and the structural formula of these reactive dyestuffs is shown in formula II:
R is in the formula II
Or
The present invention also provides the preparation method of above-mentioned formula II reactive dyestuffs, comprises the steps:
A. diazotization: K acid (3,6,8-trisulfonic acid-2-naphthylamines) is joined in the water and pulls an oar, drip sodium nitrite solution, then 0-5 ℃ of reaction add thionamic acid, removes unnecessary Sodium Nitrite, obtains diazonium salt;
B. coupled reaction: will between urea anilide hydrochloride add the water making beating, regulate pH=7-7.5, diazonium salt is added drop-wise to wherein, temperature is 20-30 ℃, reaction obtains conjugates;
C. a contracting is reacted: cyanuric chloride is added in the frozen water pull an oar, conjugates is added drop-wise to wherein, and temperature 0-5 ℃, pH=2-3, reaction obtains a contracting thing;
D. two contracting reactions: with (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid water dissolution, be added drop-wise in the contracting thing, control pH=7-7.5, temperature 30-40 ℃. reaction obtains the formula III dye solution, and spraying drying namely gets formula III dyestuff finished product;
E. hydrolysis: with formula III dyestuff finished product, be added to the water, be warming up to 50 ℃, regulate pH=9.5, react to get the formula IV dye solution, spraying drying namely gets formula IV dyestuff finished product.
The present invention also provides the application of above-mentioned reactive dyestuffs in hair, nylon fiber dyeing.
The beneficial effect that the present invention has:
Dyestuff intermediate of the present invention is than dyestuff intermediate (3-β-hydroxyethyl sulfone) aniline commonly used, many sulfonic groups, can improve well synthetic after dyestuff water-soluble.
The invention provides the Yellow active dye that is made by this new dyestuff intermediate, this Yellow active dye desired raw material cost is low, and product solubility is high, and bright in colour, and application performance is excellent, and suitability is strong, and preparation process can environmental contamination reduction.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but do not limit protection scope of the present invention.
Embodiment 1
A kind of dyestuff intermediate, the structural formula of this dyestuff intermediate be as shown in the formula (I):
The preparation method of this dyestuff intermediate comprises the steps:
1), sulfonation
With 1 part of (3-β-hydroxyethyl sulfone) oil of mirbane, slowly join in the four-hole bottle that fills 10 parts of chlorsulfonic acids, fully stir in the reinforced process, and with water bath heat preservation below 30 ℃; The reinforced post-heating to 40 ℃-60 ℃ of finishing, keep 1h (at this moment, the complete esterification of β-hydroxyethyl sulfone), reheat 180 ℃, by stratographic analysis or chromatoplate layer analysis reaction process, estimate to keep 5-6h to react completely, the rear ice that reacts completely is analysed, add refined salt, analysis of material filters and obtains filter cake is the first step intermediate product (3-β-hydroxyl second sulfone sulfate base) oil of mirbane-5-sulphonic acid chloride;
2), hydrolysis
With step 1) gained the first step intermediate product (3-β-hydroxyl second sulfone sulfate base) oil of mirbane-5-sulphonic acid chloride, be dissolved in water, heated solution is to boiling, by stratographic analysis or chromatoplate layer analysis reaction process, estimate to keep the 1-1.5h complete hydrolysis, the rear cooling that reacts completely adds refined salt, and analysis of material filters and obtains second step intermediate product (3-β-hydroxyethyl sulfone) oil of mirbane-5-sulfonic acid;
3), hydrogenating reduction
With step 2) gained second step intermediate product (3-β-hydroxyethyl sulfone) oil of mirbane-5-sulfonic acid is added to the water making beating, put in the autoclave, add the catalyzer Raney's nickel, sealing autoclave is to wherein passing into nitrogen, displace the air of the inside, and then pass into hydrogen, and be heated to 100 ℃, keep passing into hydrogen pressure 1.2MPa, reacted 5 hours, cooling discharge adds refined salt, and analysis of material filters and obtains the 3rd step intermediate product (3-β-hydroxyethyl sulfone) aniline-5-sulfonic acid;
4), esterification
With 1 part of step 3) the 3rd step intermediate product (3-β-hydroxyethyl sulfone) aniline-5-sulfonic acid joins in 6 parts of oleums, and reinforced process water is bathed insulation below 30 ℃; Then be warming up to 60 ℃ of reactions, keep more than the 2h, stratographic analysis or flaggy analytical reaction terminal point, the rear ice that reacts completely is analysed, and adds refined salt, and the analysis of material filtration obtains filter cake and namely obtains product (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid.
Product analysis
Final product is carried out stratographic analysis. chromatographic purity reaches more than 95%, adopts its product content of the amino value measuring and calculating of chemistry titration, and calculated yield reaches about 70%.
Embodiment 2
A kind of reactive dyestuffs, the structural formula of these reactive dyestuffs is shown in formula III:
Or shown in the formula IV:
The preparation method of above-mentioned reactive dyestuffs comprises the steps:
A. diazotization: 1 part of K acid (3,6,8-trisulfonic acid-2-naphthylamines) is joined in the water and pulls an oar, drip 1.02 parts sodium nitrite solution, 0-5 ℃ keeps 1h, then adds thionamic acid, removes unnecessary Sodium Nitrite, obtains diazonium salt;
B. coupled reaction: urea anilide hydrochloride between 1 part is added the water making beating, regulate pH=7-7.5 with sodium hydroxide solution, diazonium salt is added drop-wise to wherein, temperature is 20-30 ℃, continues to stir 1.5-2h, obtains conjugates;
C. a contracting reaction: with pulling an oar in 1.2 parts the cyanuric chlorides adding frozen water, conjugates is added drop-wise to wherein, temperature 0-5 ℃, pH=2-3 keeps 1-1.5h, obtains a contracting thing;
D. two contracting reactions: with 1 part of (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid water dissolution, be added drop-wise in the contracting thing control pH=7-7.5, temperature 30-40 ℃. keep 2h, obtain the formula III dye solution, spraying drying namely gets formula III dyestuff finished product;
E. hydrolysis: with formula III dyestuff finished product, be added to the water, be warming up to 50 ℃, regulate pH=9.5 with sodium hydrogen carbonate solution, react to get the formula IV dye solution, spraying drying namely gets formula IV dyestuff finished product.
Annotate: related umber is molfraction in the embodiment of the invention.
The structure that below makes for the present invention (III) reactive dyestuffs performance:
Compound of the present invention and preparation method 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 corresponding other purpose, its relevant change does not all break away from content of the present invention, all similar replacements and change will become apparent to those skilled in the art that and all be deemed to be included within the scope of the present invention.
Claims (5)
1. dyestuff intermediate is characterized in that: the structural formula of this dyestuff intermediate as shown in the formula (I):
2. the preparation method of the described dyestuff intermediate of claim 1, it is characterized in that: the method comprises the steps:
1), sulfonation
With (3-β-hydroxyethyl sulfone) oil of mirbane, join in the four-hole bottle that fills chlorsulfonic acid, fully stir in the reinforced process, and with water bath heat preservation below 30 ℃; The reinforced post-heating to 40 ℃-60 ℃ of finishing keeps 1h, reheats 180 ℃, and the rear ice that reacts completely is analysed, and adds refined salt, and analysis of material filters and obtains filter cake is the first step intermediate product (3-β-hydroxyl second sulfone sulfate base) oil of mirbane-5-sulphonic acid chloride;
2), hydrolysis
With step 1) gained the first step intermediate product (3-β-hydroxyl second sulfone sulfate base) oil of mirbane-5-sulphonic acid chloride, be dissolved in water, heated solution is to boiling, and rear cooling reacts completely, add refined salt, analysis of material filters and obtains second step intermediate product (3-β-hydroxyethyl sulfone) oil of mirbane-5-sulfonic acid;
3), hydrogenating reduction
With step 2) gained second step intermediate product (3-β-hydroxyethyl sulfone) oil of mirbane-5-sulfonic acid is added to the water making beating, put in the autoclave, add the catalyzer Raney's nickel, sealing autoclave displaces the air of the inside to wherein passing into nitrogen, and then pass into hydrogen, be heated to 100 ℃, keep passing into hydrogen pressure 1.2MPa, rear cooling discharge reacts completely, add refined salt, analysis of material filters and obtains the 3rd step intermediate product (3-β-hydroxyethyl sulfone) aniline-5-sulfonic acid;
4), esterification
With step 3) the 3rd step intermediate product (3-β-hydroxyethyl sulfone) aniline-5-sulfonic acid joins in the oleum, and reinforced process water is bathed insulation below 30 ℃; Then be warming up to 60 ℃ of reactions, the rear ice that reacts completely is analysed, and adds refined salt, and the analysis of material filtration obtains filter cake and namely obtains product (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid.
3. the application of the described dyestuff intermediate of claim 1 in preparation of dyestuff.
4. reactive dyestuffs by the preparation of the described dyestuff intermediate of claim 1, it is characterized in that: the structural formula of these reactive dyestuffs is shown in formula II:
R is in the formula II
Or
5. the preparation method of the described reactive dyestuffs of claim 4 is characterized in that: comprise the steps:
A. diazotization: K acid joined in the water pull an oar, drip sodium nitrite solution, then 0-5 ℃ of reaction add thionamic acid, removes unnecessary Sodium Nitrite, obtains diazonium salt;
B. coupled reaction: will between urea anilide hydrochloride add the water making beating, regulate pH=7-7.5, diazonium salt is added drop-wise to wherein, temperature is 20-30 ℃, reaction obtains conjugates;
C. a contracting is reacted: cyanuric chloride is added in the frozen water pull an oar, conjugates is added drop-wise to wherein, and temperature 0-5 ℃, pH=2-3, reaction obtains a contracting thing;
D. two contracting reactions: with (3-β-hydroxyl second sulfone sulfate base) aniline-5-sulfonic acid water dissolution, be added drop-wise in the contracting thing, control pH=7-7.5, temperature 30-40 ℃. reaction obtains the formula III dye solution, and spraying drying namely gets formula III dyestuff finished product;
E. hydrolysis: with formula III dyestuff finished product, be added to the water, be warming up to 50 ℃, regulate pH=9.5, react to get the formula IV dye solution, spraying drying namely gets formula IV dyestuff finished product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012103620825A CN102924348A (en) | 2012-09-25 | 2012-09-25 | Reactive dye and intermediate thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2012103620825A CN102924348A (en) | 2012-09-25 | 2012-09-25 | Reactive dye and intermediate thereof |
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| CN102924348A true CN102924348A (en) | 2013-02-13 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103756359A (en) * | 2013-12-25 | 2014-04-30 | 浙江劲光化工有限公司 | Treatment method for p-beta hydroxyethyl sulfone acetanilide mother liquor waste water |
| CN107382792A (en) * | 2017-06-07 | 2017-11-24 | 盐城市瓯华化学工业有限公司 | The intermediate aminolysis thing hydrogenation reduction method of active blue 19 8 |
| CN109232332A (en) * | 2018-10-26 | 2019-01-18 | 天津德凯化工股份有限公司 | A kind of preparation method suitable for digital ink-jet printed or dyeing dyestuff intermediate |
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| GB1494979A (en) * | 1975-08-30 | 1977-12-14 | Hoechst Ag | Process for the production of 1-aminobenzene-4-and-5-beta-sulphatoethylsulphone-2-sulphonic acid and their hydroxyethylsulphone-and vinylsulphone derivatives |
| CN1861695A (en) * | 2006-06-19 | 2006-11-15 | 湖北华丽染料工业有限公司 | Yellow ozo dye mixture and its use |
| CN101037547A (en) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | Compound active yellow dye |
-
2012
- 2012-09-25 CN CN2012103620825A patent/CN102924348A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1494979A (en) * | 1975-08-30 | 1977-12-14 | Hoechst Ag | Process for the production of 1-aminobenzene-4-and-5-beta-sulphatoethylsulphone-2-sulphonic acid and their hydroxyethylsulphone-and vinylsulphone derivatives |
| CN1861695A (en) * | 2006-06-19 | 2006-11-15 | 湖北华丽染料工业有限公司 | Yellow ozo dye mixture and its use |
| CN101037547A (en) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | Compound active yellow dye |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103756359A (en) * | 2013-12-25 | 2014-04-30 | 浙江劲光化工有限公司 | Treatment method for p-beta hydroxyethyl sulfone acetanilide mother liquor waste water |
| CN103756359B (en) * | 2013-12-25 | 2016-03-02 | 浙江劲光实业股份有限公司 | A kind for the treatment of process of p-β hydroxyethyl sulfone Acetanilide mother liquor waste water |
| CN107382792A (en) * | 2017-06-07 | 2017-11-24 | 盐城市瓯华化学工业有限公司 | The intermediate aminolysis thing hydrogenation reduction method of active blue 19 8 |
| CN109232332A (en) * | 2018-10-26 | 2019-01-18 | 天津德凯化工股份有限公司 | A kind of preparation method suitable for digital ink-jet printed or dyeing dyestuff intermediate |
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Application publication date: 20130213 |