CN100349989C - Preparation technology of azo active dyestuff - Google Patents
Preparation technology of azo active dyestuff Download PDFInfo
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- CN100349989C CN100349989C CNB2005100951582A CN200510095158A CN100349989C CN 100349989 C CN100349989 C CN 100349989C CN B2005100951582 A CNB2005100951582 A CN B2005100951582A CN 200510095158 A CN200510095158 A CN 200510095158A CN 100349989 C CN100349989 C CN 100349989C
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Abstract
The present invention relates to the preparation technology of the azo active dyestuff, the cyanuric chloride and the water are mixed sufficiently to form suspending liquid; the 2.4-sodium diaminophenylsulfonate solution is added in the suspending liquid, then, the sodium hydroxide solution is added in the suspending liquid, and the weight ratio content of the 2.4-sodium diaminophenylsulfonate from reaction to undone reaction is kept to be less than 1%; afterwards, the 3-(beta-hydroxy vinylsulfone sulfate) phenylamine and the sodium hydroxide solution are added, the weight ratio content of the 3-(beta-hydroxy vinylsulfone sulfate) phenylamine from the reaction to the undone reaction is kept to be less than 0.8%, and the hydrochloric acid and the sodium nitrite are added to take reaction to form the diazonium salt; lipoamine polyoxyvinylether and thiourea are added in the diazonium salt to be stirred sufficiently, then, the 1-amino-8-naphthol-3.6-bisulfonic acid is added, and the reaction is over when the diazonium salt disappears. The yield rate of acid coupling substance of the present invention is higher than the prior art at present by about 10 %, and the purity of the acid coupling substance is increased obviously.
Description
Technical field
The present invention relates to a kind of preparation technology of dyestuff.
Background information
The present invention relates to a kind of azo active dyestuff, the structural formula of this compound is:
In the prior art, the technology for preparing this compound is: cyanuric chloride, water, ice, adding thorough mixing under the situation of wetting agent, adding 2.4-diaminobenzene sulphur sodium, be reacted to terminal point after, add 3-(β-hydroxyalkyl vinyl sulfone acid esters) aniline again, keeping temperature is that 25-40 ℃, pH value are 5-5.5, be reacted to terminal point after, cooling on the rocks, the hydrochloric acid and the sodium nitrite solution that add specified amount carry out doazo reaction, generate diazonium salt.In diazonium salt, add under urea and the Dispersant MF condition, after stirring, add 1-amino-8-naphthol-3.6-disulfonic acid (being also referred to as H acid) solution and carry out acid condensation, keeping temperature is 0-30 ℃, pH value is 0-3, is reacted to terminal point, thereby obtains the compound of said structure formula.Reactive dyestuffs require to have enough direct colourabilitys, and simultaneously non-solid part is easy to washing, and they also should have good tint permanence and high reactivity, and above-mentioned technology synthetic dyestuff easily produces a large amount of isomer, and its structural formula is:
Therefore can not reach the requirement of above-mentioned characteristic.
Summary of the invention
The object of the invention provides a kind of preparation technology of azo active dyestuff, reduces the formation of isomer after can making this dyestuff synthetic as far as possible, and the reactive dyestuffs that make have the stability of high color fixation fastness and high fiber and dyestuff connection.
Technical scheme of the present invention is: a kind of preparation technology of azo active dyestuff, and it comprises following operation:
(1), weight part 18.4-19.8 part cyanuric chloride, 50 parts of water thorough mixing of weight part form suspension;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt;
(4), the aliphatic amine polyoxyethylene ether and the weight part 0.1-5 part thiocarbamide that in diazonium salt, add weight part 0.3-5 part, fully stir the back and add weight part 30-34.1 part 1-amino-8-naphthol-3.6-disulfonic acid, maintaining the temperature at 0-20 ℃, pH value is 0-3, and reacting disappears to diazonium salt is terminal point.
In step (1), the temperature of described suspension remains on 0～2 ℃.
The present invention compared with prior art, has following advantage: the present invention relates to aliphatic amine polyoxyethylene ether and thiocarbamide promotor as acid coupling, in the presence of above material, acid coupling is more prone to reaction, thereby has prepared highly purified desired compound.Process recovery ratio of the present invention improves about 10% apparently higher than original technology, can not produce isomer in a large number, makes in the dyestuff preparation and obtains high-purity acid coupling thing.
Embodiment
A kind of preparation technology of azo active dyestuff, it comprises following operation:
(1), 50 parts of water thorough mixing of weight part 18.4-19.8 part cyanuric chloride, weight part form suspension, the temperature of described suspension remains on 0～2 ℃;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt;
(4), the aliphatic amine polyoxyethylene ether and the weight part 0.1-5 part thiocarbamide that in diazonium salt, add weight part 0.3-5 part, fully stir the back and add weight part 30-34.1 part 1-amino-8-naphthol-3.6-disulfonic acid, maintaining the temperature at 0-20 ℃, pH value is 0-3, and reacting disappears to diazonium salt is terminal point.
With the above-mentioned acid coupling thing that reaches behind the reaction end, add sodium-chlor, and saltout, filter, prepare the even color base of C.I. Reactive Blue 222 acid that the present invention relates to.
Referring to several examples:
(1), weight part 18.4-19.8 part cyanuric chloride, 50 parts of water thorough mixing of weight part form suspension;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt; Below the preceding step of each embodiment all identical with above-mentioned steps, therefore following each embodiment only enumerates a last step.
Embodiment 1:
In 0.1 mole diazonium salt, tensio-active agent 1860 (being aliphatic amine polyoxyethylene ether) and 3.1 parts of thiocarbamides of weight part of adding 1 part of weight part, after stirring, be under the 0-3 ℃ of condition, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (being commonly called as H acid) solution of weight part 30-34.1 part in temperature, maintain the temperature at 0-20 ℃, pH value is 0-3, reacts 8 hours, and diazonium salt disappears, prepare needed C.I. Reactive Blue 222 acid coupling thing, yield is 92%.
Embodiment 2:
In the diazonium salt of 0.1mol, tensio-active agent 1860 (being aliphatic amine polyoxyethylene ether) and 6 parts of thiocarbamides of weight part of adding 2.5 parts of weight parts, after stirring, be under the 0-3 ℃ of condition, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (being commonly called as H acid) solution of weight part 30-34.1 part in temperature, maintain the temperature at 0-20 ℃, pH value is 0-3, reacts 8 hours, and diazonium salt disappears, prepare C.I. Reactive Blue 222 acid coupling thing, yield is 80%.
Comparative example 1:
In the diazonium salt of 0.1mol, auxiliary agent MF and 5 parts of urea of adding 1.5 parts of weight parts, in good stirring and temperature is under the 0-3 ℃ of condition, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (H acid) solution of weight part 30-34.1 part, keeping temperature is 0-20 ℃, and pH value is 0-3, reacted 8 hours, diazonium salt disappears, and prepares C.I. Reactive Blue 222 acid coupling thing, and yield is 80%.
Comparative example 2:
In the diazonium salt of 0.1mol, do not add any auxiliary agent, under good stirring, be under the 0-3 ℃ of condition in temperature, slowly add 1-amino-8-naphthol-3.6-disulfonic acid (H acid) solution of weight part 30-34.1 part, maintain the temperature at 0-20 ℃, pH value is 0-3, reacts 8 hours, and diazonium salt disappears, prepare C.I. Reactive Blue 222 acid coupling thing, yield is 70%.
Claims (2)
1, a kind of preparation technology of azo active dyestuff is characterized in that: it comprises following operation:
(1), weight part 18.4-19.8 part cyanuric chloride, 50 parts of water thorough mixing of weight part form suspension;
(2), 21 parts of 2.4-diamino benzene sulfonic acids of weight part sodium solution is added in the suspension, in suspension, add sodium hydroxide solution again, the pH value of suspension is remained between the 2.5-3, keep reaction to unreacted 2.4-diamino benzene sulfonic acid sodium weight ratio content less than 1%;
(3), add weight part 28-30 part 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline again, be warmed up to 25-40 ℃, adding sodium hydroxide solution accent pH value is 5-5.5, keep reaction to unreacted 3-(β-hydroxyalkyl vinyl sulfone sulfate) aniline weight ratio content less than 0.8%, be cooled to 0～5 ℃, add 25-28 part hydrochloric acid and 6.21-6.9 part Sodium Nitrite reaction back and form diazonium salt;
(4), the aliphatic amine polyoxyethylene ether and the weight part 0.1-5 part thiocarbamide that in diazonium salt, add weight part 0.3-5 part, fully stir the back and add weight part 30-34.1 part 1-amino-8-naphthol-3.6-disulfonic acid, maintaining the temperature at 0-20 ℃, pH value is 0-3, and reacting disappears to diazonium salt is terminal point.
2, the preparation technology of azo active dyestuff according to claim 1 is characterized in that: in step (1), the temperature of described suspension remains on 0～2 ℃.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2005100951582A CN100349989C (en) | 2005-10-27 | 2005-10-27 | Preparation technology of azo active dyestuff |
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| CNB2005100951582A CN100349989C (en) | 2005-10-27 | 2005-10-27 | Preparation technology of azo active dyestuff |
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| CN1752150A CN1752150A (en) | 2006-03-29 |
| CN100349989C true CN100349989C (en) | 2007-11-21 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311369A (en) * | 2011-09-13 | 2012-01-11 | 吴江桃源染料有限公司 | Preparation method of 1-amino-2-(4-sulfonic acid azobenzene)-8-hydroxy-3,6-disulfonic acid |
| CN104140690B (en) * | 2014-07-29 | 2016-06-08 | 嘉兴瑞奕环保科技有限公司 | AZOpigments acid idol reaction promoter and application thereof |
| CN104327542A (en) * | 2014-10-13 | 2015-02-04 | 天津德凯化工股份有限公司 | Red reactive dye and its preparation method |
| CN115466524A (en) * | 2022-09-02 | 2022-12-13 | 浙江劲光实业股份有限公司 | Synthesis method of reactive dye |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1108348C (en) * | 2000-10-24 | 2003-05-14 | 泰兴市锦鸡染料有限公司 | Reactive azo orange dye and its preparing process |
| CN1597789A (en) * | 2004-08-02 | 2005-03-23 | 吴江桃源染料厂 | Preparation technology of azo active dye |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1108348C (en) * | 2000-10-24 | 2003-05-14 | 泰兴市锦鸡染料有限公司 | Reactive azo orange dye and its preparing process |
| CN1597789A (en) * | 2004-08-02 | 2005-03-23 | 吴江桃源染料厂 | Preparation technology of azo active dye |
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