CN103627200A - Direct dye and preparation method thereof - Google Patents
Direct dye and preparation method thereof Download PDFInfo
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- CN103627200A CN103627200A CN201310602735.7A CN201310602735A CN103627200A CN 103627200 A CN103627200 A CN 103627200A CN 201310602735 A CN201310602735 A CN 201310602735A CN 103627200 A CN103627200 A CN 103627200A
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Abstract
The invention relates to a direct dye and a preparation method thereof. The black dye has a general structural formula (I), is bright in color and low in price, and is an important cotton dye; a dyeing method is easy and convenient.
Description
Technical field
The invention belongs to substantive dyestuff field, particularly a kind of black direct dye that is applicable to cotton, fiber crops dyeing and preparation method thereof.
Background technology
Substantive dyestuff is the cotton main consumptive material with dyestuff, is important cotton dyestuff.Substantive dyestuff does not need mordant and dyes directly, and beautiful in colour, cheap, and dyeing process is easy.And black dyes is the dye of current cellulose dyeing large usage quantity.
Summary of the invention
The technical problem to be solved in the present invention has been to provide the black dyes of a kind of following structural formula (I), and this black dyes is beautiful in colour, cheap, dyeing process is easy.
The technical solution used in the present invention is:
A black dyes, this black dyes has the general structure of structural formula (I):
R wherein
1for structural formula (1-1) is to the arbitrary substituting group in structural formula (1-3):
R
2for structural formula (1-4) is to the arbitrary substituting group in structural formula (1-6):
M is H or basic metal.
Preferably, M be-Na or-K.
The present invention also provides the preparation method of the compound of structural formula (I), comprises the steps:
1), the preparation of color base:
In retort, add water, again 1-hydroxyl-7-amino-3-naphthene sulfonic acid is added in tank and is pulled an oar, adjust pH=6-7.5 to dissolve, be warming up to T=30-55 ℃ and drip acetic anhydride, dropping limit, limit is warming up to T=50-70 ℃, reaction 10-30 minute, detect qualified after, be cooled to T=20-35 ℃, adjust pH=6.5-8.5 to keep temperature, pH reaction, obtain acylate, standby;
In another retort, add water, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, add ice to be cooled to T≤3 ℃, add hydrochloric acid, add sodium nitrite solution, keep nitrous acid micro-excessive, react to obtain diazonium salt I, standby;
Described diazonium salt I is joined in described acylate, adjust pH=5-7.5, T=13-30 ℃ of reaction.It is qualified to detect, and adds NaOH solid, and is warming up to T=80-100 ℃ of reaction, after reaction, saltouts, and press filtration, obtains color base filter cake;
2), color base diazotization:
By the making beating of color base filter cake, make the complete pulp of its filter cake, add ice to be cooled to T≤3 ℃, add hydrochloric acid, add sodium nitrite solution, carry out diazotization reaction, obtain diazonium salt II, standby;
3), a step coupled reaction:
In retort, add water, H acid is added in tank and pulled an oar, adjust pH=4.5-8.5 to dissolving completely, obtain H acid solution.
In another retort, add water, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, and adds ice to be cooled to T≤3 ℃, adds hydrochloric acid, adds sodium nitrite solution, reacts to obtain diazonium salt III;
Drip H acid solution to described diazonium salt III, drip and finish, react to obtain a step conjugates; Standby;
4), two step coupled reactions:
Diazonium salt II is joined in a step conjugates, and reaction makes two step conjugates, makes the black dyes of structural formula (I).
Further, the method also comprises step 5), saltout refining: in two step conjugates, add NaCl, adjust pH≤5 simultaneously, saltout, it is qualified to detect, and carries out press filtration, obtain filter cake and be dyestuff finished product.
More specifically, the preparation method of the compound of this structural formula (I), comprises the steps:
1), the preparation of color base:
In retort, add water, amino-3 naphthene sulfonic acid of 1-hydroxyl-7-are added in tank and are pulled an oar, with 30%NaOH solution, adjust pH=6-7.5 to dissolve, be warming up to T=30-55 ℃ and drip acetic anhydride, dropping limit, limit is warming up to T=50-70 ℃, reaction 10-30 minute, detect qualified after, be cooled to T=20-35 ℃, with 30%NaOH solution, adjust pH=6.5-8.5 to keep temperature, pH reaction, detect qualified after, obtain acylate, standby;
In another retort, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, and adds ice to be cooled to T≤3 ℃, add hydrochloric acid, add sodium nitrite solution, keep nitrous acid micro-excessive, reaction 3-5 hour, thionamic acid is except nitrous acid, eliminate, obtain diazonium salt I, standby;
Described diazonium salt I is joined in described acylate, and soda ash is adjusted pH=5-7.5, T=13-30 ℃ of reaction.It is qualified to detect, and adds the NaOH solid of reaction solution volume 3-15%, and is warming up to T=80-100 ℃ of reaction, and it is qualified to detect.Add the NaCl of reaction solution volume 5-20% to saltout, qualified rear press filtration, obtains color base filter cake;
2), color base diazotization:
The making beating of color base filter cake, makes the complete pulp of its filter cake, adds ice to be cooled to T≤3 ℃, adds hydrochloric acid, adds sodium nitrite solution, carries out diazotization 2-5 hour, and thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt II, standby.
3), a step coupled reaction:
In retort, add water, H acid is added in tank and pulled an oar, 30%NaOH solution adjusts pH=4.5-8.5 to dissolving completely, obtains H acid solution;
In another retort, add water, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, and adds ice to be cooled to T≤3 ℃, adds hydrochloric acid, adds sodium nitrite solution, keeps nitrous acid micro-excessive, reaction 3-5 hour.Thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt III, standby; Sodium bicarbonate is adjusted pH=1.5-4, and T=5-30 ℃ drips H acid solution to described diazonium salt III, and used time 0.5-3.5 hour, drips and finish, reaction 5-20 hour, and it is qualified to detect, and obtains a step conjugates, standby.
4), two step coupled reactions:
Described diazonium salt II is joined in a step conjugates, and soda ash is adjusted pH=5-9, T=10-40 ℃ of reaction 1-4 hour, and it is qualified to detect, and obtains two step conjugates, makes the black dyes of structural formula (I).
5), saltout refining:
The NaCl that adds volume 10-40% in two step conjugates adjusts pH≤5 simultaneously, saltouts, and it is qualified to detect, and carries out press filtration, obtains filter cake and is dyestuff finished product
The 30%NaOH solution that the present invention mentions is 30% (weight) NaOH solution.
The beneficial effect that the present invention has:
Black dyes of the present invention is beautiful in colour, cheap, and dyeing process is easy.It is important cotton dyestuff.
Embodiment
Below in conjunction with specific embodiment, the present invention will be further described, but do not limit protection scope of the present invention.
Embodiment 1
A black dyes, the structural formula of this dyestuff is as follows:
The preparation method of this dyestuff, comprises the steps:
1, the preparation of color base:
Add end water 3000kg; amino-3 naphthene sulfonic acid of the 1-hydroxyl of 310.5kg-7-are added in 20T tank and are pulled an oar, with 30%NaOH solution, adjust pH=6.5-7 to dissolve, be warming up to T=35-40 ℃ and drip 172.5kg acetic anhydride; dropping limit, limit is warming up to T=60-65 ℃; react 20 minutes, detect qualified after, be cooled to T=25-30 ℃; with 30%NaOH solution, adjust pH=7-7.5 to keep temperature, pH reaction; detect qualified after, obtain acylate, standby.
Add end water 3000kg, by 357.5kg aniline-2,5-disulfonic acid adds in 10T tank pulls an oar, and adds 1000kg ice to be cooled to T≤3 ℃, add 62kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 91.5kg), keep nitrous acid micro-excessive, react 2 hours, add 1kg thionamic acid to remove nitrous acid, eliminate, obtain diazonium salt I, standby.
Above-mentioned diazonium salt I is joined in acylate to soda ash (Na
2cO
3) adjust pH=6-6.5, T=15-20 ℃ of reaction, it is qualified to detect, and adds the NaOH solid of 520kg, and is warming up to T=95-100 ℃ of reaction, and it is qualified to detect.Add the NaCl of 1580kg to saltout, qualified rear press filtration, obtains color base filter cake.
2, color base diazotization:
In 10T tank, add end water 3000kg, add the making beating of color base filter cake, make the complete pulp of its filter cake, add 1000kg ice to be cooled to T≤3 ℃, add 47.5kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 90kg), carry out diazotization 2 hours.1kg thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt II, standby.
3, a step coupled reaction:
In 10T tank, add end water 3000kg, add 341kgH acid making beating, 30%NaOH solution adjusts pH=6.5-7.5 to dissolving completely, obtains H acid solution.
In 20T tank, add end water 2000kg, add the making beating of 231kg Sodium sulfanilate, add 800kg ice, be cooled to T≤3 ℃, add 92kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 70.5kg), keep nitrous acid micro-excessive, react 2 hours.1kg thionamic acid is except nitrous acid, eliminates standbyly, obtains diazonium salt III.Sodium bicarbonate is adjusted pH=2-2.5, and T=5-10 ℃ drips H acid solution to described diazonium salt III, 1 hour used time, dropwise, and react 12 hours, it is qualified to detect, and obtains a step conjugates, standby.
4, two step coupled reactions:
Diazonium salt II is joined in a step conjugates, and soda ash is adjusted pH=7.5-8.5, and T=20-25 ℃, reacts 2 hours, and it is qualified to detect, and obtains two step conjugates, makes this black dyes.
5, saltout refining:
The NaCl that adds 2650kg in two step conjugates adjusts pH≤5 with hydrochloric acid simultaneously, saltouts, and it is qualified to detect, and carries out press filtration, obtains filter cake and is dyestuff finished product.
The dyeing data of this black dyes are:
Fastness is with 4% concentration that dyes:
Embodiment 2:
A black dyes, the structural formula of this dyestuff is as follows:
The preparation method of this dyestuff, comprises the steps:
1, the preparation of color base:
Add end water 3000kg, amino-3 naphthene sulfonic acid of the 1-hydroxyl of 310.5kg-7-are added in 20T tank and are pulled an oar, with 30%NaOH solution, adjust pH=6.5-7 to dissolve, be warming up to T=35-40 ℃ and drip 172.5kg acetic anhydride, dropping limit, limit is warming up to T=60-65 ℃, react 20 minutes, detect qualified after, be cooled to T=20-25 ℃, with 30%NaOH solution, adjust pH=7-7.5 to keep temperature, pH reaction, detect qualified after, obtain acylate; Standby.
Add end water 3000kg, by 357.5kg aniline-2,5-disulfonic acid adds in 10T tank pulls an oar, and adds 1000kg ice to be cooled to T≤3 ℃, adds 62kg hydrochloric acid, adds sodium nitrite solution (containing Sodium Nitrite 91.5kg), keeps nitrous acid micro-excessive, reacts 2 hours.Add 1kg thionamic acid to remove nitrous acid, eliminate, obtain diazonium salt I, standby.
Described diazonium salt I is joined in acylate, and soda ash is adjusted pH=6.5-7.5, T=15-20 ℃ of reaction, and it is qualified to detect, and adds the NaOH solid of 520kg, and is warming up to T=95-100 ℃ of reaction, and it is qualified to detect.Add the NaCl of 1580kg to saltout, qualified rear press filtration, obtains color base filter cake.
2, color base diazotization:
In 10T tank, add end water 3000kg, add the making beating of color base filter cake, make the complete pulp of its filter cake, add 1000kg ice to be cooled to T≤3 ℃, add 47.5kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 90kg), carry out diazotization 2 hours.1kg thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt II, standby.
3, a step coupled reaction:
In 10T tank, add end water 3000kg, add 341kgH acid making beating, 30%NaOH solution adjusts pH=6.5-7.5 to dissolving completely, obtains H acid solution.
In 20T tank, add end water 2000kg, add the making beating of 231kg m-sulfanilic acid sodium, add 800kg ice, be cooled to T≤3 ℃, add 92kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 70.5kg), keep nitrous acid micro-excessive, react 2 hours.1kg thionamic acid, except nitrous acid, eliminates to obtain diazonium salt III, standby; Sodium bicarbonate is adjusted pH=2-2.5, and T=5-10 ℃ drips H acid solution to described diazonium salt III, 1 hour used time, dropwise, react 12 hours, it is qualified to detect, a step conjugates, standby.
4, two step coupled reactions:
Diazonium salt II is joined in a step conjugates, and soda ash is adjusted pH=7-8, and T=20-25 ℃, reacts 2 hours, and it is qualified to detect, and obtains two step conjugates, makes this black dyes.
5, saltout refining:
The NaCl that adds 2650kg in two step conjugates adjusts pH≤5 with hydrochloric acid simultaneously, saltouts, and it is qualified to detect, and carries out press filtration, obtains filter cake and is dyestuff finished product.
The dyeing data of this black dyes are:
Fastness is with 4% concentration that dyes:
Embodiment 3
A black dyes, the structural formula of this dyestuff is as follows:
The preparation method of this dyestuff, comprises the steps:
1, the preparation of color base:
Add end water 3000kg; amino-3 naphthene sulfonic acid of the 1-hydroxyl of 310.5kg-7-are added in 20T tank and are pulled an oar, with 30%NaOH solution, adjust pH=6.5-7 to dissolve, be warming up to T=35-40 ℃ and drip 172.5kg acetic anhydride; dropping limit, limit is warming up to T=60-65 ℃; react 20 minutes, detect qualified after, be cooled to T=20-25 ℃; with 30%NaOH solution, adjust pH=7-7.5 to keep temperature, pH reaction; detect qualified after, obtain acylate, standby.
Add end water 3000kg, 231kg Sodium sulfanilate is added in 10T tank and pulled an oar, add 1000kg ice to be cooled to T≤3 ℃, add 62kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 91.5kg), keep nitrous acid micro-excessive, react 2 hours.Add 1kg thionamic acid to remove nitrous acid, eliminate, obtain diazonium salt I, standby.
Above-mentioned diazonium salt I is joined in acylate, and soda ash is adjusted pH=6.5-7, T=15-20 ℃ of reaction.It is qualified to detect, and adds the NaOH solid of 520kg, and is warming up to T=95-100 ℃ of reaction, and it is qualified to detect.Add the NaCl of 1580kg to saltout, qualified rear press filtration, obtains color base filter cake.
2, color base diazotization:
In 10T tank, add end water 3000kg, add the making beating of color base filter cake, make the complete pulp of its filter cake, add 1000kg ice to be cooled to T≤3 ℃, add 47.5kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 90kg), carry out diazotization 2 hours.1kg thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt II, standby.
3, a step coupled reaction:
In 10T tank, add end water 3000kg, add 341kgH acid making beating, 30%NaOH solution adjusts pH=5.5-6 to dissolving completely, obtains H acid solution.
In 20T tank, add end water 2000kg, add 357.5kg aniline-2, the making beating of 5-disulfonic acid, add 800kg ice, be cooled to T≤3 ℃, add 92kg hydrochloric acid, add sodium nitrite solution (containing Sodium Nitrite 70.5kg), keep nitrous acid micro-excessive, react 2 hours.1kg thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt III, standby.Sodium bicarbonate is adjusted pH=2-2.5, and T=5-10 ℃ drips H acid solution to described diazonium salt III, 1 hour used time, dropwise, and react 12 hours, it is qualified to detect, and obtains a step conjugates, standby.
4, two step coupled reactions:
Diazonium salt II is joined in a step conjugates, and soda ash is adjusted pH=7.5-8, and T=20-25 ℃ is reacted 2 hours, and it is qualified to detect, and obtains two step conjugates, makes this black dyes.
5, saltout refining:
The NaCl that adds 2650kg in two step conjugates adjusts pH≤5 with hydrochloric acid simultaneously, saltouts, and it is qualified to detect, and carries out press filtration, obtains filter cake and is dyestuff finished product.
The dyeing data of this black dyes are:
Fastness is with 4% concentration that dyes:
Claims (4)
1. a black dyes, is characterized in that: this black dyes has the general structure of structural formula (I):
R wherein
1for structural formula (1-1) is to the arbitrary substituting group in structural formula (1-3):
R
2for structural formula (1-4) is to the arbitrary substituting group in structural formula (1-6):
M is H or basic metal.
2. black dyes according to claim 1, is characterized in that: described M for-Na or-K.
3. the preparation method of the black dyes described in claim 1 or 2, is characterized in that: comprise the steps:
1), the preparation of color base:
In retort, add water, again 1-hydroxyl-7-amino-3-naphthene sulfonic acid is added in tank and is pulled an oar, adjust pH=6-7.5 to dissolve, be warming up to T=30-55 ℃ and drip acetic anhydride, dropping limit, limit is warming up to T=50-70 ℃, reaction 10-30 minute, detect qualified after, be cooled to T=20-35 ℃, adjust pH=6.5-8.5 to keep temperature, pH reaction, obtain acylate, standby;
In another retort, add water, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, add ice to be cooled to T≤3 ℃, add hydrochloric acid, add sodium nitrite solution, keep nitrous acid micro-excessive, react to obtain diazonium salt I, standby;
Described diazonium salt I is joined in described acylate, adjust pH=5-7.5, T=13-30 ℃ of reaction.It is qualified to detect, and adds NaOH solid, and is warming up to T=80-100 ℃ of reaction, after reaction, saltouts, and press filtration, obtains color base filter cake;
2), color base diazotization:
By the making beating of color base filter cake, make the complete pulp of its filter cake, add ice to be cooled to T≤3 ℃, add hydrochloric acid, add sodium nitrite solution, carry out diazotization reaction, obtain diazonium salt II, standby;
3), a step coupled reaction:
In retort, add water, H acid is added in tank and pulled an oar, adjust pH=4.5-8.5 to dissolving completely, obtain H acid solution.
In another retort, add water, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, and adds ice to be cooled to T≤3 ℃, adds hydrochloric acid, adds sodium nitrite solution, reacts to obtain diazonium salt III;
Drip H acid solution to described diazonium salt III, drip and finish, react to obtain a step conjugates; Standby;
4), two step coupled reactions:
Diazonium salt II is joined in a step conjugates, and reaction makes two step conjugates, makes the black dyes of structural formula (I).
4. the preparation method of black dyes according to claim 3, is characterized in that: comprise the steps:
1), the preparation of color base:
In retort, add water, amino-3 naphthene sulfonic acid of 1-hydroxyl-7-are added in tank and are pulled an oar, with 30%NaOH solution, adjust pH=6-7.5 to dissolve, be warming up to T=30-55 ℃ and drip acetic anhydride, dropping limit, limit is warming up to T=50-70 ℃, reaction 10-30 minute, detect qualified after, be cooled to T=20-35 ℃, with 30%NaOH solution, adjust pH=6.5-8.5 to keep temperature, pH reaction, detect qualified after, obtain acylate, standby;
In another retort, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, and adds ice to be cooled to T≤3 ℃, add hydrochloric acid, add sodium nitrite solution, keep nitrous acid micro-excessive, reaction 3-5 hour, thionamic acid is except nitrous acid, eliminate, obtain diazonium salt I, standby;
Described diazonium salt I is joined in described acylate, and soda ash is adjusted pH=5-7.5, T=13-30 ℃ of reaction.It is qualified to detect, and adds the NaOH solid of reaction solution volume 3-15%, and is warming up to T=80-100 ℃ of reaction, and it is qualified to detect.Add the NaCl of reaction solution volume 5-20% to saltout, qualified rear press filtration, obtains color base filter cake;
2), color base diazotization:
The making beating of color base filter cake, makes the complete pulp of its filter cake, adds ice to be cooled to T≤3 ℃, adds hydrochloric acid, adds sodium nitrite solution, carries out diazotization 2-5 hour, and thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt II, standby.
3), a step coupled reaction:
In retort, add water, H acid is added in tank and pulled an oar, 30%NaOH solution adjusts pH=4.5-8.5 to dissolving completely, obtains H acid solution;
In another retort, add water, by m-sulfanilic acid sodium, Sodium sulfanilate or aniline-2,5-disulfonic acid adds in tank pulls an oar, and adds ice to be cooled to T≤3 ℃, adds hydrochloric acid, adds sodium nitrite solution, keeps nitrous acid micro-excessive, reaction 3-5 hour.Thionamic acid, except nitrous acid, eliminates, and obtains diazonium salt III, standby; Sodium bicarbonate is adjusted pH=1.5-4, and T=5-30 ℃ drips H acid solution to described diazonium salt III, and used time 0.5-3.5 hour, drips and finish, reaction 5-20 hour, and it is qualified to detect, and obtains a step conjugates, standby.
4), two step coupled reactions:
Described diazonium salt II is joined in a step conjugates, and soda ash is adjusted pH=5-9, T=10-40 ℃ of reaction 1-4 hour, and it is qualified to detect, and obtains two step conjugates, makes the black dyes of structural formula (I).
5), saltout refining:
The NaCl that adds volume 10-40% in two step conjugates adjusts pH≤5 simultaneously, saltouts, and it is qualified to detect, and carries out press filtration, obtains filter cake and is dyestuff finished product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104327545A (en) * | 2014-10-13 | 2015-02-04 | 天津德凯化工股份有限公司 | Dark blue reactive dye |
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