CN102911523A - Blue reactive dye and preparation method thereof - Google Patents
Blue reactive dye and preparation method thereof Download PDFInfo
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- CN102911523A CN102911523A CN2012103617042A CN201210361704A CN102911523A CN 102911523 A CN102911523 A CN 102911523A CN 2012103617042 A CN2012103617042 A CN 2012103617042A CN 201210361704 A CN201210361704 A CN 201210361704A CN 102911523 A CN102911523 A CN 102911523A
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Abstract
The invention relates to a blue reactive dye and a preparation method of the blue reactive dye. The blue reactive dye has a structural formula shown in the specification. The invention also provides the preparation method of the reactive dye. The blue reactive dye prepared by the invention has excellent water resistance, high solubility, high dyeing rate, and wet treatment fastness resistant to wet friction.
Description
Technical field
The invention belongs to the reactive dyestuffs field, particularly relate to a kind of blue active dye that is applicable to pure cotton dyeing and hair and synthetic dyeing and preparation method thereof.
Background technology
The dye that textiles is commonly used at present is matching stain, acid mordant dye and metallized dye, owing to the material that dyes with these kinds of dyes, fastness is not good enough, coloured light is gorgeous not, but also can cause trouble to environmental protection, because the restriction of environmental ecology, more and more higher for the requirement of dye uptake, degree of fixation and the waste water from dyestuff of dyestuff.Reactive dyestuffs are beautiful in colour with it, it is convenient to use, with fiber with covalent bonds, have excellent fastness ability and more and more be widely used in dyeing process.
Digital ink-jet printed dye ink is the main consumptive material that digital inking printing is produced, and has become the requisite integral part in ink-jet printed field, also is the emphasis that the fine chemicals research field is used in current weaving.The process of dying on the ink-jet printed dyestuff is diffused in the fiber with molecularity goes, require dyestuff itself that stronger water-soluble and good degree of fixation is arranged, and reactive dyestuffs are a kind of water-soluble dyes, chromatogram is complete, bright-colored, be used to the important colourity material of preparing ink-jet printed dye ink, from the development trend of dyestuff, water-soluble and the high colour-fast rate of reactive dyestuffs excellence satisfies environmental requirement, meets the printing in textiles requirement.
The purpose of this invention is to provide a kind of blue active dye, has good water tolerance, high-dissolvability, high dye uptake, the wet colour fastness of moisture-proof friction, blue dyes is again one of dominant hue of dyestuff, it is the dye of present dyeing keratin-fiber consumption maximum, be suitable for cotton, hair, the dyeing of nylon and blended textile, and be fit to ink-jet printed dyestuff.
Summary of the invention
The technical problem to be solved in the present invention is: provide a kind of good water tolerance that has, high-dissolvability, high dye uptake, the blue active dye of the wet colour fastness of moisture-proof friction.
The technical solution used in the present invention is:
A kind of blue active dye, this blue active dye have following formula I structural formula:
R arbitrary substituting group that is following structural formula (II-1) to the structural formula (II-12) wherein:
M is H or basic metal.
Preferably, M be-K or-Na.
Preferably, R is the arbitrary substituting group in formula (II-3), (II-4), (II-7), (II-9).
The present invention also provides the preparation method of said structure formula (I) reactive dyestuffs, comprises the steps:
1), the preparation of color base:
Bromamine acid is put into heating for dissolving in the tank, add sodium bicarbonate, M acid, cuprous chloride, temperature T=80 ℃-90 ℃ of insulations cooled to below 40 ℃ after 4-5 hour, then to wherein adding diatomite, stir after one hour and filter, the filtrate of having filtered is transferred to pH=7.0-7.5 with hydrochloric acid, be warmed up to 50 ℃-60 ℃, equitemperature adds gac after reaching assigned temperature, stir after one hour and filter, the color base that has filtered is warmed up to 70 ℃-75 ℃, add hydrochloric acid, add again refined salt, stir after 2 hours and filter, the color base filter cake after filtering is pulled an oar the solid content of colour examining base under acidic conditions, adding water makes the solid content of color base in the pulping process at 35%-40%, the long-time stirring makes the color base filter cake become pulpous state fully, and the Dry Sack based sols is stand-by;
2), a contracting reaction:
On the rocks in the reactor, cyanuric chloride behind the ice mill, drips step 1) gained color base solution, control T=0 ℃-5 ℃, pH=6.0-6.5 reacts to get a contracting liquid;
3), two contracting reactions:
Any compound in the following structural formula (III-1) to (III-12) is dissolved with soda ash, then joins step 2) in the contracting liquid, be warming up to 30-35 ℃, control pH=7.0-7.5, react complete, get two contracting liquid, namely make structural formula (I) reactive dyestuffs.
In the aforesaid method, the compound with contracting liquid reaction in the step 3) is preferably 2-amino-4-sulfonic benzoic acid, 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid, aniline-2,5-disulfonic acid and 2-amino naphthalenes-3,6, any in the 8-trisulfonic acid.
Above-mentioned 4-(N-hydroxyethylamino) aniline-3-sulfonic acid prepares by the following method: the p-Nitrophenyl chloride ortho-sulfonic acid is added the water making beating, with the sodium hydroxide solution pH=7.0-7.5 that neutralizes, filtration obtains neutralized reaction product and the Virahol mixing is warmed up to 80 ℃-90 ℃ backflows one hour, then in mixture, in 3 hours, drip off Monoethanolamine MEA BASF, insulation is 80 ℃-90 ℃ in the dropping process, drip off rear insulation after 1 hour cold analysis filter to get filter cake, the solution that filter cake is made into 10wt% is put into autoclave and is added the logical hydrogen reducing of catalyzer (Raney's nickel), pass into the pressure of hydrogen at 1.2-1.4Pa, temperature is controlled at 90 ℃-100 ℃, insulation is more than 5 hours, remove by filter catalyzer, obtain solution and regulate pH=1.0-1.5 with the hydrochloric acid of 30wt%, separate out filtration and obtain the 4-(N-hydroxyethylamino) aniline-3-sulfonic acid.
Reaction process is as follows:
4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid prepares by the following method: with the above-mentioned 4-(N-hydroxyethylamino that makes) aniline-3-sulfonic acid carries out esterification with 98% the vitriol oil, dry, namely get 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid.
In the above-mentioned steps, the structure of related material is as follows:
The present invention also provides the application of reactive dyestuffs in cotton fiber dyeing of above-mentioned formula (I).
The present invention also provides the application of reactive dyestuffs in digital ink-jet printed dyestuff of above-mentioned formula (I).
The beneficial effect that the present invention has:
The blue active dye that the present invention makes has good water tolerance, high-dissolvability, high dye uptake, the wet colour fastness of moisture-proof friction.
Embodiment
Further specify the present invention below by specific embodiment, but do not limit protection scope of the present invention.
Embodiment 1
A kind of blue active dye has such as the formula IV structural formula:
The preparation method of this blue active dye comprises the steps:
1), color base preparation:
The 425kg bromamine acid is put into heating for dissolving in 10 tons of tanks, adds 350kg sodium bicarbonate, 253kg M acid, the 10kg cuprous chloride, temperature T=80 ℃-90 ℃ be incubateds and cool to below 40 ℃ after 5 hours, then to wherein adding 40kg diatomite, stir filtration after a hour.The filtrate of having filtered is transferred to pH=7.0-7.5 with hydrochloric acid, be warmed up to 50 ℃-60 ℃, when reaching assigned temperature (50 ℃-60 ℃), equitemperature adds gac 60kg-80kg, stir after one hour and filter, the color base that has filtered is warmed up to 70 ℃-75 ℃, the hydrochloric acid soln that adds 486kg 30wt%, add refined salt 175 kg, stir after 2 hours and to filter, add the hydrochloric acid soln of 150kg 30wt% in the color base filter cake after filter, the solid content of colour examining base, adding water makes the solid content of color base in the pulping process at 35%-40%, the long-time stirring makes the color base filter cake become pulpous state fully, and the Dry Sack based sols is stand-by;
2), a contracting reaction:
In 20 tons of retort, add 1500 tons of ice, 190 kg cyanuric chlorides, ice mill cyanuric chloride is after five minutes, drip step 1) the color base solution that makes, pH=6.0-6.5 is controlled with soda ash solution in condensation course control temperature T=0 ℃-5 ℃, react after 4.5 hours, get a contracting liquid, carry out two contracting reactions.
3), two contracting reactions:
517kg 2-amino-5-sulfonic benzoic acid is neutralized with soda ash, make the pH=6.0-6.5 of solution, then join step 2) a contracting liquid in, be warming up to 30 ℃-35 ℃, pH=7.0-7.5 with soda ash control two contracting reactants, react 3 hours afterreactions complete, get two contracting liquid, namely make the reactive dyestuffs of structure formula IV.
The formula IV blue active dye dyes cotton application performance table
Embodiment 2
A kind of blue active dye, this dyestuff have formula (V) structural formula:
The preparation method of this blue active dye comprises the steps:
1), the 4-(N-sulfuric ester ethylamino) preparation of aniline-3-sulfonic acid:
P-Nitrophenyl chloride ortho-sulfonic acid 500kg is added the water making beating, with the sodium hydroxide solution pH=7.0-7.5 that neutralizes, the neutralized reaction product that filtration obtains and Virahol 750kg mix, being warmed up to 80 ℃-90 ℃ refluxed one hour, then in mixture, in 3 hours, drip off the 60kg Monoethanolamine MEA BASF, insulation is 80 ℃-90 ℃ in the dropping process, drip off rear insulation cold analysis filtration after 1 hour, the solution that the filter cake that cold analysis is filtered is made into 10wt% is put into autoclave and is added the logical hydrogen reducing of catalyzer, pass into the pressure of hydrogen at 1.2-1.4Pa, temperature is controlled at 90 ℃-100 ℃, and insulation is more than 5 hours, then remove by filter catalyzer, obtain solution and regulate pH=1.0-1.5 with the hydrochloric acid soln of 30wt%, separate out to filter and obtain product, the product that obtains is carried out esterification with 98% the vitriol oil, dry, obtain 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid.
2), the preparation of color base
The bromamine acid of 450kg is put into heating for dissolving in 10 tons of tanks, adds 370kg sodium bicarbonate, the M acid of 265kg, the 10kg cuprous chloride, temperature T=80 ℃-90 ℃ are incubated and cool to below 40 ℃ after 5 hours, then to wherein adding 45kg diatomite, stir after one hour and filter.The filtrate of having filtered is transferred pH=7.0-7.5 with hydrochloric acid, be warmed up to 50 ℃-60 ℃, when reaching 50 ℃-60 ℃, equitemperature adds gac 60 kg-80 kg, stir sampling detection after a hour, the qualified rear filtration of liquid chromatographic detection, the color base that has filtered is warmed up to 70 ℃-75 ℃, the hydrochloric acid soln that adds 515kg 30wt% adds refined salt 185kg, stirs after 2 hours and filters, add the hydrochloric acid soln of 160kg 30wt% in the color base filter cake after filter, the solid content of colour examining base adds solid content that water makes color base in the pulping process at 35%-40%, and long-time the stirring makes the color base filter cake become pulpous state fully, the Dry Sack based sols, stand-by;
3), a contracting reaction:
In 20 tons of retort, add 1500 tons of ice, the 198kg cyanuric chloride, ice mill cyanuric chloride is after five minutes, drip step 2) gained color base solution, make it control temperature T=0 ℃-5 ℃ at condensation course, control pH=6.0-6.5 with soda ash solution, react after 4.5 hours, get a contracting liquid.
4), two contracting reactions:
With 315kg 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid neutralizes with soda ash, make the pH=6.0-6.5 of solution, then join step 3) in the contracting liquid, be warming up to 30 ℃-35 ℃, pH=7.0-7.5 with soda ash control two contracting reactants, be incubated reaction in 3 hours complete, get two contracting liquid, namely make the reactive dyestuffs of structural formula (V).
Formula (V) blue active dye dyes cotton application performance table
Embodiment 3
A kind of blue active dye, this dyestuff has the formula VI structural formula:
The preparation method of this blue active dye comprises the steps:
1), color base preparation:
The bromamine acid of 425kg is put into heating for dissolving in 10 tons of tanks, adds 350kg sodium bicarbonate, the M acid of 253kg, the 10kg cuprous chloride, temperature T=80 ℃-90 ℃ are incubated and cool to below 40 ℃ after 5 hours, then to wherein adding 40kg diatomite, stir after one hour and filter.The filtrate of having filtered is transferred to pH=7.0-7.5 with hydrochloric acid, be warmed up to 50 ℃-60 ℃, add gac 60 kg-80 kg. when equitemperature reaches 50 ℃-60 ℃ and stir filtration after a hour, the color base that has filtered is warmed up to 70 ℃-75 ℃, the hydrochloric acid soln that adds 486kg 30wt%, add refined salt 175 kg, stir after 2 hours and filter, add the hydrochloric acid soln of 150kg 30wt% in the color base filter cake after filter, the solid content of colour examining base adds solid content that water makes color base in the pulping process at 35%-40%, and long-time the stirring makes the color base filter cake become pulpous state fully, the Dry Sack based sols, stand-by;
2), a contracting reaction:
In 20 tons of retort, add 1500 tons of ice, the 190kg cyanuric chloride, ice mill cyanuric chloride is after five minutes, drip step 1) gained color base solution, pH=6.0-6.5 is controlled with soda ash solution in condensation course control temperature T=0 ℃-5 ℃, react after 4.5 hours, get a contracting liquid, treat two contractings.
3), two contracting reactions:
With 489kg 2-amino naphthalenes-3,6, the 8-trisulfonic acid neutralizes with soda ash, makes the pH=6.0-6.5 of solution, then joins step 2) in the contracting liquid, be warming up to 30 ℃-35 ℃, with the pH=7.0-7.5 value of soda ash control two contracting reactants.React three hours afterreactions complete, get two contracting liquid, namely make the reactive dyestuffs of structure formula VI.
The formula VI blue active dye dyes cotton application performance table
Embodiment 4
A kind of blue active dye, this dyestuff have formula (VII) structural formula:
The preparation method of this blue active dye comprises the steps:
1), color base preparation:
The bromamine acid of 450kg is put into heating for dissolving in 10 tons of tanks, adds 370kg sodium bicarbonate, the M acid of 265kg, the 10kg cuprous chloride, temperature T=80 ℃-90 ℃ be incubateds 5 hours to below 40 ℃, then to wherein adding 45kg diatomite, stir filtration after a hour.Excessively complete filtrate is transferred to pH=7.0-7.5 with hydrochloric acid, be warmed up to 50 ℃-60 ℃, add gac 60kg-80 kg. when equitemperature reaches 50 ℃-60 ℃ and stir sampling detection after a hour, the qualified rear filtration of liquid chromatographic detection, the color base that has filtered is warmed up to 70 ℃-75 ℃, the hydrochloric acid soln that adds 515kg 30wt%, add refined salt 185 kg, stir after 2 hours and to filter, add the hydrochloric acid soln of 160kg 30wt% in the color base filter cake after filter, the solid content of colour examining base, adding water makes the solid content of color base in the pulping process at 35%-40%, the long-time stirring makes the color base filter cake become pulpous state fully, and the Dry Sack based sols is stand-by;
2), a contracting reaction:
In 20 tons of retort, add 1500 tons of ice, the 198kg cyanuric chloride, ice mill cyanuric chloride is after five minutes, drip step 1) gained color base solution, pH=6.0-6.5 is controlled with soda ash solution in condensation course control temperature T=0 ℃-5 ℃, react after 4.5 hours, get a contracting liquid.
3), two contracting reactions:
With 305kg aniline-2, the 5-disulfonic acid neutralizes with soda ash, make the pH=6.0-6.5 of solution, then join step 2) in the contracting liquid, be warming up to 30 ℃-35 ℃, with the pH=7.0-7.5 of soda ash control two contracting reactants, react three hours afterreactions complete, get two contracting liquid, namely make the reactive dyestuffs of structural formula (VII).
Formula (VII) blue active dye dyes cotton application performance table
Method of the present invention 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 (7)
1. blue active dye, it is characterized in that: this blue active dye has following formula I structural formula:
R arbitrary substituting group that is following structural formula (II-1) to the structural formula (II-12) wherein:
M is H or basic metal.
2. a kind of blue active dye according to claim 1 is characterized in that: described M for-K or-Na.
3. a kind of blue active dye according to claim 1 and 2, it is characterized in that: described R is the arbitrary substituting group in formula (II-3), (II-4), (II-7), (II-9).
4. the preparation method of claim 1 or 2 described structural formula (I) reactive dyestuffs is characterized in that: comprise the steps:
1), the preparation of color base:
Bromamine acid is put into heating for dissolving in the tank, add sodium bicarbonate, M acid, cuprous chloride, temperature T=80 ℃-90 ℃ of insulations cooled to below 40 ℃ after 4-5 hour, then to wherein adding diatomite, stir after one hour and filter, the filtrate of having filtered is transferred to pH=7.0-7.5 with hydrochloric acid, be warmed up to 50 ℃-60 ℃, equitemperature adds gac after reaching assigned temperature, stir after one hour and filter, the color base that has filtered is warmed up to 70 ℃-75 ℃, add hydrochloric acid, add again refined salt, stir after 2 hours and filter, the color base filter cake after filtering is pulled an oar the solid content of colour examining base under acidic conditions, adding water makes the solid content of color base in the pulping process at 35%-40%, the long-time stirring makes the color base filter cake become pulpous state fully, and the Dry Sack based sols is stand-by;
2), a contracting reaction:
On the rocks in the reactor, cyanuric chloride behind the ice mill, drips step 1) gained color base solution, control T=0 ℃-5 ℃, pH=6.0-6.5 reacts to get a contracting liquid;
3), two contracting reactions:
Any compound in the following structural formula (III-1) to (III-12) is dissolved with soda ash, then joins step 2) in the contracting liquid, be warming up to 30-35 ℃, control pH=7.0-7.5, react complete, get two contracting liquid, namely make structural formula (I) reactive dyestuffs.
5. method according to claim 4, it is characterized in that: the compound with contracting liquid reaction in the step 3) is 2-amino-4-sulfonic benzoic acid, 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid, aniline-2,5-disulfonic acid and 2-amino naphthalenes-3, in 6, the 8-trisulfonic acid any.
6. method according to claim 4, it is characterized in that: described 4-(N-hydroxyethylamino) aniline-3-sulfonic acid prepares by the following method: the p-Nitrophenyl chloride ortho-sulfonic acid is added the water making beating, with the sodium hydroxide solution pH=7.0-7.5 that neutralizes, filtration obtains neutralized reaction product and the Virahol mixing is warmed up to 80 ℃-90 ℃ backflows one hour, then in mixture, in 3 hours, drip off Monoethanolamine MEA BASF, insulation is 80 ℃-90 ℃ in the dropping process, drip off rear insulation after 1 hour cold analysis filter to get filter cake, the solution that filter cake is made into 10wt% is put into autoclave and is added the logical hydrogen reducing of catalyzer (Raney's nickel), pass into the pressure of hydrogen at 1.2-1.4Pa, temperature is controlled at 90 ℃-100 ℃, insulation is more than 5 hours, remove by filter catalyzer, obtain solution and regulate pH=1.0-1.5 with the hydrochloric acid of 30wt%, separate out filtration and obtain the 4-(N-hydroxyethylamino) aniline-3-sulfonic acid.
7. according to claim 4 or 5 described methods, it is characterized in that: described 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid prepares by the following method: the p-Nitrophenyl chloride ortho-sulfonic acid is added the water making beating, with the sodium hydroxide solution pH=7.0-7.5 that neutralizes, filtration obtains neutralized reaction product and the Virahol mixing is warmed up to 80 ℃-90 ℃ backflows one hour, then in mixture, in 3 hours, drip off Monoethanolamine MEA BASF, insulation is 80 ℃-90 ℃ in the dropping process, drip off rear insulation after 1 hour cold analysis filter to get filter cake, the solution that filter cake is made into 10wt% is put into autoclave and is added the logical hydrogen reducing of catalyzer (Raney's nickel), pass into the pressure of hydrogen at 1.2-1.4Pa, temperature is controlled at 90 ℃-100 ℃, insulation is more than 5 hours, remove by filter catalyzer, obtain solution and regulate pH=1.0-1.5 with the hydrochloric acid of 30wt%, separate out to filter and obtain the 4-(N-hydroxyethylamino) aniline-3-sulfonic acid, with the above-mentioned 4-(N-hydroxyethylamino that makes) aniline-3-sulfonic acid carries out esterification with 98% the vitriol oil, dry, namely get 4-(N-sulfuric ester ethylamino) aniline-3-sulfonic acid.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103602099A (en) * | 2013-11-27 | 2014-02-26 | 天津德凯化工股份有限公司 | Blue reactive dye |
| CN106349120A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Dye intermediate and preparation method |
| CN103553983B (en) * | 2013-10-31 | 2017-10-24 | 天津德凯化工股份有限公司 | A kind of novel dye intermediate and the reactive dye as made from the intermediate |
| CN110016237A (en) * | 2019-04-04 | 2019-07-16 | 深圳市墨库图文技术有限公司 | A kind of preparation method of blue dyes color base |
| CN112679980A (en) * | 2020-12-21 | 2021-04-20 | 江苏德美科化工有限公司 | High-performance double-color-body brilliant blue reactive dye and preparation method thereof |
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| CN1158926A (en) * | 1995-11-23 | 1997-09-10 | 希巴特殊化学控股公司 | Process for dichromatic or trichromatic dyeing or printing |
| CN1720299A (en) * | 2002-12-02 | 2006-01-11 | 西巴特殊化学品控股有限公司 | Reactive dyes, a process for their preparation and their use |
| CN102618073A (en) * | 2012-02-21 | 2012-08-01 | 浙江亿得化工有限公司 | Blue double-reactive-group dye compound, as well as preparation method and composition thereof |
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| CN1158926A (en) * | 1995-11-23 | 1997-09-10 | 希巴特殊化学控股公司 | Process for dichromatic or trichromatic dyeing or printing |
| CN1720299A (en) * | 2002-12-02 | 2006-01-11 | 西巴特殊化学品控股有限公司 | Reactive dyes, a process for their preparation and their use |
| CN102618073A (en) * | 2012-02-21 | 2012-08-01 | 浙江亿得化工有限公司 | Blue double-reactive-group dye compound, as well as preparation method and composition thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103553983B (en) * | 2013-10-31 | 2017-10-24 | 天津德凯化工股份有限公司 | A kind of novel dye intermediate and the reactive dye as made from the intermediate |
| CN103602099A (en) * | 2013-11-27 | 2014-02-26 | 天津德凯化工股份有限公司 | Blue reactive dye |
| CN103602099B (en) * | 2013-11-27 | 2017-12-15 | 天津德凯化工股份有限公司 | A kind of blue active dye |
| CN106349120A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Dye intermediate and preparation method |
| CN110016237A (en) * | 2019-04-04 | 2019-07-16 | 深圳市墨库图文技术有限公司 | A kind of preparation method of blue dyes color base |
| CN112679980A (en) * | 2020-12-21 | 2021-04-20 | 江苏德美科化工有限公司 | High-performance double-color-body brilliant blue reactive dye and preparation method thereof |
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Application publication date: 20130206 |