CN104327545A - Dark blue reactive dye - Google Patents
Dark blue reactive dye Download PDFInfo
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- CN104327545A CN104327545A CN201410540239.8A CN201410540239A CN104327545A CN 104327545 A CN104327545 A CN 104327545A CN 201410540239 A CN201410540239 A CN 201410540239A CN 104327545 A CN104327545 A CN 104327545A
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Abstract
The invention relates to a dark blue reactive dye, the reactive dye has the structural general formula shown as (I). The dye is a navy blue single structure reactive dye, improves the shortcoming that navy blue is obtained by color matching in the prior art, has the advantages of simple structure, low price of raw materials, high color fixation and high fastness, can be used for dyeing cotton, wool, nylon and other fiber, and is especially suitable for nylon fiber dyeing, and the dyeing process has the advantages of good reproducibility and stability, simple preparation process and easy operation.
Description
Technical field
The present invention relates to reactive dyestuff field, particularly be a kind of dark blue reactive dye and preparation method thereof.
Background technology
Current reactive dyestuffs have been popularize very much for the dyeing of cellulosic fibre, and it has lovely luster.The features such as fastness ability is good, easy to use.But along with the continuous renewal of dye techniques, high colour-fast rate, high-performance dyestuff becomes main development direction.Be applicable to nylon dark blue reactive dye at present mostly obtained by colorant match, but colorant match process receives the control of the series of factors such as the coloured light intensity of former dyestuff and impact makes that finished product is unstable or process is complicated.Dyestuff of the present invention is a kind of navy single structure reactive dyestuffs.Which improve and obtained atroceruleous shortcoming by colorant match in the past, and structure is simple, low in raw material price, high fixation, high fastness.Can be used for the dyeing of the fibers such as cotton, hair, nylon, be particularly applicable to the dyeing of nylon fiber, dyeing course has good circulation ratio and stability, and preparation process is simple, convenient operation.
Summary of the invention
The object of the invention is preparation dark blue reactive dye, these reactive dyestuffs have such as formula (I) general structure:
In formula (I), described R
1for
Present invention also offers the preparation method of above-mentioned reactive dyestuffs, comprise the steps:
A () .4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 4-3-β hydroxyethyl sulfuryl sulfate ester aniline, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid in step (a) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminated remaining nitrous acid, regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
(d). diazotization: the compound of formula (Y-1), formula (Y-2), formula (Y-3) or formula (Y-4) or formula (Y-5) is carried out diazotization, obtains diazonium salt;
(e) alkaline coupling: step (d) gained reaction solution is joined step (c) gained reaction solution, pH=7 ~ 8.5 are regulated with industrial sodium carbonate solution, react 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
F () alkaline purification: step (e) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects conjugates complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, i.e. obtained formula (I) reactive dyestuffs.
Preferably, the structural formula of these reactive dyestuffs is such as formula shown in (II):
Present invention also offers the preparation method of above-mentioned formula (II) reactive dyestuffs, comprise the steps
A () .4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 4-3-β hydroxyethyl sulfuryl sulfate ester aniline, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid in step (a) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminated remaining nitrous acid, regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
D () .6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd making beating: be added to the water by 6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd, making beating makes material particles even, for subsequent use.
(e). diazotization: add hydrochloric acid by step (d) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, has reacted rear thionamic acid and has eliminated remaining nitrous acid, for subsequent use.
(f) alkaline coupling: step (e) gained reaction solution is joined step (c) gained reaction solution, regulates pH=7 ~ 8.5 with industrial sodium carbonate solution.React 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
G () alkaline purification: step (f) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects alkaline coupling product complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, for subsequent use.
H () is saltoutd: in step (g) reactant, add sodium-chlor saltout, and stirs filtration in 1 hour, collects filter cake.
(i) spraying dry: add water step (h) gained filter cake making beating, and spraying dry, obtains finished product dyestuff.
Preferably, the structural formula of these reactive dyestuffs is as shown in formula III:
Present invention also offers the preparation method of above-mentioned formula III reactive dyestuffs, comprise the steps
A () .4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 4-3-β hydroxyethyl sulfuryl sulfate ester aniline, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid in step (a) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminated remaining nitrous acid, regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
(d). 100% sulfuric acid is warming up to≤70 DEG C slowly add Sodium Nitrite, 70 DEG C insulation 1 ~ 2 hour, solution, to limpid, obtains nitrous dilute sulphuric acid, for subsequent use.
(e). diazotization: 6-β hydroxyethyl sulfuryl sulfuric ester-2-naphthylamines slowly adds in step (d) gains, control temperature is lower than 20 DEG C, and be warming up to 30 ~ 40 DEG C of insulations two hours, ice dilutes to obtain diazonium salt, for subsequent use.
(f) alkaline coupling: step (e) gained reaction solution is joined step (c) gained reaction solution, regulates pH=7 ~ 8.5 with industrial sodium carbonate solution.React 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
G () alkaline purification: step (f) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects alkaline coupling product complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, for subsequent use.
H () is saltoutd: in step (g) reactant, add sodium-chlor saltout, and stirs filtration in 1 hour, collects filter cake.
(i) spraying dry: add water step (h) gained filter cake making beating, and spraying dry, obtains finished product dyestuff.
The structural formula of these reactive dyestuffs is as shown in formula IV:
Present invention also offers the preparation method of above-mentioned formula IV reactive dyestuffs, comprise the steps
A () .4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 4-3-β hydroxyethyl sulfuryl sulfate ester aniline, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid in step (a) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminated remaining nitrous acid, regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
D () .1-naphthylamine-4-sulfonic acid sodium is pulled an oar: be added to the water by naphthalidine-4-sodium sulfonate, and making beating makes material particles even, for subsequent use.
(e). diazotization: add hydrochloric acid by step (d) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, has reacted rear thionamic acid and has eliminated remaining nitrous acid, for subsequent use.
(f) alkaline coupling: step (e) gained reaction solution is joined step (c) gained reaction solution, regulates pH=7 ~ 8.5 with industrial sodium carbonate solution.React 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
G () alkaline purification: step (f) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects alkaline coupling product complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, for subsequent use.
H () is saltoutd: in step (g) reactant, add sodium-chlor saltout, and stirs filtration in 1 hour, collects filter cake.
(i) spraying dry: add water step (h) gained filter cake making beating, and spraying dry, obtains finished product dyestuff.
The beneficial effect that the present invention has:
Dyestuff of the present invention is a kind of navy single structure reactive dyestuffs.Which improve and obtained atroceruleous shortcoming by colorant match in the past, and structure is simple, low in raw material price, high fixation, high fastness.Can be used for the dyeing of the fibers such as cotton, hair, nylon, be particularly applicable to the dyeing of nylon fiber, dyeing course has good circulation ratio and stability, and preparation process is simple, convenient operation.
Embodiment
In order to understand the present invention, further illustrate the present invention with embodiment below, but do not limit the present invention.
Embodiment 1
A kind of dark blue reactive dye, has the structural formula of formula (II)
The preparation method of the reactive dyestuffs of formula (II) structural formula, comprises the steps:
A () .4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for the 4-of 100% amount 3-β hydroxyethyl sulfuryl sulfate ester aniline 15.78g, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid 15.8g in step (a) solution, ice 200g, add Sodium Nitrite (containing the industrial sodium nitrite 7.33g) solution of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminate remaining nitrous acid, pH=2.0 ~ 3.0 are regulated with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder 19.23g in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 15 DEG C of conditions.
D () .6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd making beating: be added to the water by 6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd 20.56g, making beating makes material particles even, for subsequent use.
(e). diazotization: add hydrochloric acid 15.8g by step (d) solution, ice 200g, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, has reacted rear thionamic acid and has eliminated remaining nitrous acid, for subsequent use.
(f) alkaline coupling: step (e) gained reaction solution is joined step (c) gained reaction solution, regulates pH=7 ~ 8.5 with industrial sodium carbonate solution.React 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
G () alkaline purification: step (f) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects alkaline coupling product complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, for subsequent use.
H () is saltoutd: the sodium-chlor adding volume ratio 10 ~ 15% in step (g) reactant is saltoutd, and stirs filtration in 1 hour, collects filter cake.
(i) spraying dry: add water step (h) gained filter cake making beating, and spraying dry, obtains finished product dyestuff.
The performance of the dyestuff in the embodiment of the present invention 1 is as follows:
| Light fastness | Metal to-metal contact | Wet friction | To soap colourity | Acid sweat stain colourity | Alkali sweat stain colourity |
| 4 grades | 4 grades | 4 grades | 4-5 level | 4-5 level | 3-4 level |
| Cellulose acetate fibre staining | Cotton staining | Polymeric amide staining | Polyester staining | Acrylic fibers staining | Wool staining | |
| Soap | 4 grades | 4 grades | 4-5 level | 4 grades | 4-5 level | 4 grades |
| Acid sweat stain | 4 grades | 4 grades | 4 grades | 4 grades | 4-5 level | 3-4 level |
| Alkali sweat stain | 4 grades | 3-4 level | 4 grades | 4 grades | 4 grades | 4-5 level |
Embodiment 2
A kind of dark blue reactive dye, has the structural formula of formula III
The preparation method of the reactive dyestuffs of formula III structural formula, comprises the steps:
A () 4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 100%4-3-β hydroxyethyl sulfuryl sulfate ester aniline 15.78g, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid 15.8g in step (a) solution, ice 200g, add the sodium nitrite solution (containing industrial sodium nitrite 7.33g) of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminate remaining nitrous acid, pH=2.0 ~ 3.0 are regulated with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder 19.23g in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
(d). 100% sulfuric acid 45g is warming up to≤70 DEG C slowly add Sodium Nitrite (containing industrial sodium nitrite 7.33g), 70 DEG C insulation 1 ~ 2 hour, solution, to limpid, obtains nitrous dilute sulphuric acid, for subsequent use.
(e). diazotization: the 6-β hydroxyethyl sulfuryl sulfuric ester-2-naphthylamines 16.55g of 100% amount slowly adds in step (d) gains, control temperature is lower than 20 DEG C, and be warming up to 30 ~ 40 DEG C of insulations two hours, ice dilutes to obtain diazonium salt, for subsequent use.
(f) alkaline coupling: step (e) gained reaction solution is joined step (c) gained reaction solution, regulates pH=7 ~ 8.5 with industrial sodium carbonate solution.React 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
G () alkaline purification: step (f) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects alkaline coupling product complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, for subsequent use.
H () is saltoutd: the sodium-chlor adding volume ratio 10 ~ 15% in step (g) reactant is saltoutd, and stirs filtration in 1 hour, collects filter cake.
(i) spraying dry: add water step (h) gained filter cake making beating, and spraying dry, obtains finished product dyestuff.
The performance of the dyestuff in the embodiment of the present invention 2 is as follows:
| Light fastness | Metal to-metal contact | Wet friction | To soap colourity | Acid sweat stain colourity | Alkali sweat stain colourity |
| 4 grades | 4 grades | 4 grades | 4-5 level | 4-5 level | 3-4 level |
| Cellulose acetate fibre staining | Cotton staining | Polymeric amide staining | Polyester staining | Acrylic fibers staining | Wool staining | |
| Soap | 4 grades | 4 grades | 4-5 level | 4 grades | 4-5 level | 4 grades |
| Acid sweat stain | 4 grades | 4 grades | 4 grades | 4 grades | 4-5 level | 3-4 level |
| Alkali sweat stain | 4 grades | 3-4 level | 4 grades | 4 grades | 4 grades | 4-5 level |
Embodiment 3
A kind of dark blue reactive dye, has the structural formula of formula IV
The preparation method of the reactive dyestuffs of formula IV structural formula, comprises the steps:
A () 4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 100%4-3-β hydroxyethyl sulfuryl sulfate ester aniline 15.78g, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid 15.8g in step (a) solution, ice 200g, add the sodium nitrite solution (containing industrial sodium nitrite 7.33g) of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminate remaining nitrous acid, pH=2.0 ~ 3.0 are regulated with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder 19.23g in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
D () .1-naphthylamine-4-sulfonic acid sodium is pulled an oar: be added to the water by naphthalidine-4-sodium sulfonate 12.3g, and making beating makes material particles even, for subsequent use.
(e). diazotization: add hydrochloric acid 15.8g by step (d) solution, ice 200g, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, has reacted rear thionamic acid and has eliminated remaining nitrous acid, for subsequent use.
(f) alkaline coupling: step (e) gained reaction solution is joined step (c) gained reaction solution, regulates pH=7 ~ 8.5 with industrial sodium carbonate solution.React 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
G () alkaline purification: step (f) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects alkaline coupling product complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, for subsequent use.
H () is saltoutd: the sodium-chlor adding volume ratio 10 ~ 15% in step (g) reactant is saltoutd, and stirs filtration in 1 hour, collects filter cake.
(i) spraying dry: add water step (h) gained filter cake making beating, and spraying dry, obtains finished product dyestuff.
The performance of the dyestuff in the embodiment of the present invention 3 is as follows:
| Light fastness | Metal to-metal contact | Wet friction | To soap colourity | Acid sweat stain colourity | Alkali sweat stain colourity |
| 4 grades | 4 grades | 4 grades | 4-5 level | 4-5 level | 3-4 level |
| Cellulose acetate fibre staining | Cotton staining | Polymeric amide staining | Polyester staining | Acrylic fibers staining | Wool staining | |
| Soap | 4 grades | 4 grades | 4-5 level | 4 grades | 4-5 level | 4 grades |
| Acid sweat stain | 4 grades | 4 grades | 4 grades | 4 grades | 4-5 level | 3-4 level |
| Alkali sweat stain | 4 grades | 3-4 level | 4 grades | 4 grades | 4 grades | 4-5 level |
A kind of dark blue reactive dye 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 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 (2)
1. a dark blue reactive dye, is characterized in that: these reactive dyestuffs have such as formula (I) general structure:
In formula (I), described R
1for
2. the preparation method of reactive dyestuffs described in claim 1, is characterized in that: comprise the steps:
A () .4-chloro-3-β hydroxyethyl sulfuryl sulfate ester aniline is pulled an oar: be added to the water by chloro-for 4-3-β hydroxyethyl sulfuryl sulfate ester aniline, and making beating makes material particles even, for subsequent use.
(b). diazotization: add hydrochloric acid in step (a) solution, ice, adds the sodium nitrite solution of dissolving fast, diazotization reaction 2 hours, react rear thionamic acid and eliminated remaining nitrous acid, regulate pH=2.0 ~ 3.0 with industrial sodium bicarbonate, for subsequent use.
(c). acid coupling: add H acid powder in step (b) reaction solution, stirring reaction 5 ~ 10 hours under temperature 5 ~ 20 DEG C of conditions.
(d). diazotization: the compound of formula (Y-1), formula (Y-2), formula (Y-3) or formula (Y-4) or formula (Y-5) is carried out diazotization, obtains diazonium salt;
(e) alkaline coupling: step (d) gained reaction solution is joined step (c) gained reaction solution, pH=7 ~ 8.5 are regulated with industrial sodium carbonate solution, react 3 ~ 5 hours under temperature 5 ~ 25 DEG C of conditions, tlc detection of acidic coupling product complete reaction is without remaining as terminal, for subsequent use.
F () alkaline purification: step (e) reaction solution is warming up to 50 ~ 55 DEG C, regulates pH=9 ~ 9.5 with aqueous sodium carbonate, reacts 3 hours.It is terminal that thin-layer chromatography detects conjugates complete reaction, hydrochloric acid readjustment pH=6.0 ~ 8.0, i.e. obtained formula (I) reactive dyestuffs.
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| CN201410540239.8A CN104327545A (en) | 2014-10-13 | 2014-10-13 | Dark blue reactive dye |
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|---|---|---|---|
| CN201410540239.8A CN104327545A (en) | 2014-10-13 | 2014-10-13 | Dark blue reactive dye |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59115360A (en) * | 1982-12-22 | 1984-07-03 | Sumitomo Chem Co Ltd | Disazo compound and method for dyeing fiber by using the same |
| JPH0532908A (en) * | 1990-08-28 | 1993-02-09 | Sumitomo Chem Co Ltd | Bisazo compound and method for dyeing or printing fiber material using the same compound |
| CN102433027A (en) * | 2011-09-28 | 2012-05-02 | 天津德凯化工股份有限公司 | Azo blue active dye and preparation method thereof |
| CN102504585A (en) * | 2011-09-28 | 2012-06-20 | 天津德凯化工股份有限公司 | Blue active dye, preparation method and application thereof |
| CN102504586A (en) * | 2011-09-28 | 2012-06-20 | 天津德凯化工股份有限公司 | Blue reactive dye and its preparation method |
| CN102504584A (en) * | 2011-09-28 | 2012-06-20 | 天津德凯化工股份有限公司 | Azo type blue reactive dye, and its preparation method and application |
| CN103030994A (en) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | Dye reactive blue used for pure cotton dyeing |
| CN103627200A (en) * | 2013-11-22 | 2014-03-12 | 天津德凯化工股份有限公司 | Direct dye and preparation method thereof |
-
2014
- 2014-10-13 CN CN201410540239.8A patent/CN104327545A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59115360A (en) * | 1982-12-22 | 1984-07-03 | Sumitomo Chem Co Ltd | Disazo compound and method for dyeing fiber by using the same |
| JPH0532908A (en) * | 1990-08-28 | 1993-02-09 | Sumitomo Chem Co Ltd | Bisazo compound and method for dyeing or printing fiber material using the same compound |
| CN103030994A (en) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | Dye reactive blue used for pure cotton dyeing |
| CN102433027A (en) * | 2011-09-28 | 2012-05-02 | 天津德凯化工股份有限公司 | Azo blue active dye and preparation method thereof |
| CN102504585A (en) * | 2011-09-28 | 2012-06-20 | 天津德凯化工股份有限公司 | Blue active dye, preparation method and application thereof |
| CN102504586A (en) * | 2011-09-28 | 2012-06-20 | 天津德凯化工股份有限公司 | Blue reactive dye and its preparation method |
| CN102504584A (en) * | 2011-09-28 | 2012-06-20 | 天津德凯化工股份有限公司 | Azo type blue reactive dye, and its preparation method and application |
| CN103627200A (en) * | 2013-11-22 | 2014-03-12 | 天津德凯化工股份有限公司 | Direct dye and preparation method thereof |
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Application publication date: 20150204 |