CN104327543A - Navy blue nylon reactive dye - Google Patents

Navy blue nylon reactive dye Download PDF

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Publication number
CN104327543A
CN104327543A CN201410539332.7A CN201410539332A CN104327543A CN 104327543 A CN104327543 A CN 104327543A CN 201410539332 A CN201410539332 A CN 201410539332A CN 104327543 A CN104327543 A CN 104327543A
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solution
acid
subsequent use
reaction
diazotization
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张兴华
马志坚
曹世川
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Tianjin Dek Chemical Co Ltd
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Tianjin Dek Chemical Co Ltd
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Priority to CN201410539332.7A priority Critical patent/CN104327543A/en
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Abstract

The invention relates to a navy blue nylon reactive dye. The structural general formula of the reactive dye is represented by formula (I) shown in the specification. The dye is a navy blue single-structured reactive dye. The reactive dye improves the disadvantage of the previous obtaining of a navy blue color through color matching, has the advantages of simple structure, cheap raw materials, high color fixation and high fastness, and can be used for dyeing cotton, animal hair, nylon and other fibers, especially nylon fibers, the dyeing process has very good reappearance and stability, and the preparation process reactive dye is simple and is convenient to operate.

Description

A kind of navy nylon reactive dye
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)
R 1for-SO 2cH 2cH 2oH or-SO 2cH=CH 2or-H;
R 2for-H or-Cl or-NO 2or-OCH 3or-NHCH 2cH 2oH;
R 3for-H or-Cl.
Present invention also offers the preparation method of above-mentioned reactive dyestuffs, comprise the steps:
(a). making beating: the compound of formula (Y-1) is added to the water, making beating makes material particles even, for subsequent use;
Wherein X 1for-SO 2cH 2cH 2oH or-SO 2cH 2cH 2oSO 3h or-H;
X 2for-H or-Cl or-NO 2or-OCH 3or-NHCH 2cH 2oH;
X 3for-H or-Cl;
(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: 6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd is added to the water, 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, 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 () .3-β hydroxyethyl sulfuryl-4-chloroaniline is pulled an oar: be added to the water by 3-β hydroxyethyl sulfuryl-4-chloroaniline, 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 such as formula shown in (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 () .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 IV:
Present invention also offers the preparation method of above-mentioned formula IV reactive dyestuffs, comprise the steps
(a). Ortho-Chloro aniline is pulled an oar: be added to the water by Ortho-Chloro 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.
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 () .3-β hydroxyethyl sulfuryl-4-chloroaniline is pulled an oar: be added to the water by the 3-β hydroxyethyl sulfuryl-4-chloroaniline 11.8g of 100% amount, 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 the 6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd 20.56g of 100% amount, making beating makes material particles even, for subsequent use.
(e). diazotization: add hydrochloric acid 15.8g by step (d) solution, ice 200g, adds Sodium Nitrite (containing the industrial sodium nitrite 7.33g) solution of dissolving, diazotization reaction 2 hours fast, react rear thionamic acid and eliminate 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 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 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). Ortho-Chloro aniline is pulled an oar: be added to the water by the Ortho-Chloro aniline 6.378g of 100% amount, 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 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)
R 1for-SO 2cH 2cH 2oH or-SO 2cH=CH 2or-H;
R 2for-H or-Cl or-NO 2or-OCH 3or-NHCH 2cH 2oH;
R 3for-H or-Cl.
2. the preparation method of reactive dyestuffs described in claim 1, is characterized in that: comprise the steps:
(a). making beating: the compound of formula (Y-1) is added to the water, making beating makes material particles even, for subsequent use;
Wherein X 1for-SO 2cH 2cH 2oH or-SO 2cH 2cH 2oSO 3h or-H;
X 2for-H or-Cl or-NO 2or-OCH 3or-NHCH 2cH 2oH;
X 3for-H or-Cl;
(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: 6-β hydroxyethyl sulfuryl sulfuric ester-2-amino-1-naphthalene sulfonic aicd is added to the water, 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, i.e. obtained formula (I) reactive dyestuffs.
CN201410539332.7A 2014-10-13 2014-10-13 Navy blue nylon reactive dye Pending CN104327543A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0068204A1 (en) * 1981-06-15 1983-01-05 Sumitomo Chemical Company, Limited Reactive mono-functional bisazo blue-black dye
US20050166339A1 (en) * 2002-03-22 2005-08-04 Dystar Textilfarben Gmbh & Co.Deutschland Kg Dye mixtures of fiber-reactive azo dyes, their preparation and use
CN103031004A (en) * 2010-08-27 2013-04-10 天津德凯化工股份有限公司 Reactive blue dye and its preparation method
CN103044960A (en) * 2010-08-27 2013-04-17 天津德凯化工股份有限公司 Dye reactive blue and preparation method thereof
CN103642273A (en) * 2013-11-21 2014-03-19 天津德凯化工股份有限公司 Active black dye composition suitable for dyeing polyamide fibers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0068204A1 (en) * 1981-06-15 1983-01-05 Sumitomo Chemical Company, Limited Reactive mono-functional bisazo blue-black dye
US20050166339A1 (en) * 2002-03-22 2005-08-04 Dystar Textilfarben Gmbh & Co.Deutschland Kg Dye mixtures of fiber-reactive azo dyes, their preparation and use
CN103031004A (en) * 2010-08-27 2013-04-10 天津德凯化工股份有限公司 Reactive blue dye and its preparation method
CN103044960A (en) * 2010-08-27 2013-04-17 天津德凯化工股份有限公司 Dye reactive blue and preparation method thereof
CN103642273A (en) * 2013-11-21 2014-03-19 天津德凯化工股份有限公司 Active black dye composition suitable for dyeing polyamide fibers

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
浙江大学等: "《化学工艺学(精编版)》", 31 December 2011, 高等教育出版社 *
田铁牛: "《中等专业学校教材—有机合成单元过程》", 31 July 1999, 化学工业出版社 *

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Application publication date: 20150204