CN101723863B - Preparation method of purple active dye - Google Patents
Preparation method of purple active dye Download PDFInfo
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- CN101723863B CN101723863B CN 200910228236 CN200910228236A CN101723863B CN 101723863 B CN101723863 B CN 101723863B CN 200910228236 CN200910228236 CN 200910228236 CN 200910228236 A CN200910228236 A CN 200910228236A CN 101723863 B CN101723863 B CN 101723863B
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- sodium hydroxide
- acid
- aniline
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Abstract
The invention provides a preparation method of a purple active dye, which comprises the steps of condensing, diazotizing, coupling, neutralizing, drying and debrominating. The method has low production cost; the product can be used for independently dyeing wool fiber or with the other dyes, has good dyeing capability, fresh colored light, good color fastness; and particularly, the dyed wool fiber has good dye rate and color fixation rate.
Description
Technical field
The present invention relates to active dye technical field, particularly relate to a kind of preparation method of purple active dye.
Background technology
Now general dyeing wool, cashmere, used dyestuff are matching stain, acid mordant dye and metallized dye.Because with the material that these kinds of dyes are dyed, fastness is all not good enough, coloured light is not really gorgeous, but also can cause trouble to environmental protection.Get into 21 century because the restriction of environmental ecology, for dye uptake, degree of fixation and dyeing waste-water require increasingly high.Matching stain can not satisfy development of times again.
Summary of the invention
Technical problem to be solved by this invention is, provides one can reduce environmental pollution, and the desired raw material cost is low; Product solubility is high, and bright in colour, and application performance is excellent; Easy to use; The purple active dye for wool that suitability is strong particularly, the invention provides the preparation method of the compound of following formula (I):
This method comprises the steps:
The dissolving of A, H acid
With H acid dilution dissolving, with the sodium hydroxide solution neutralization, and the adjustment strength of solution.
B, condensation reaction
4-carboxyl benzene sulfonyl chloride is added the H acid solution, with carrying out condensation reaction behind the sodium hydroxide adjustment pH value.
C, 4-(2 ', 3 '-dibromo propionamido)-aniline dissolving
4-(2 ', 3 '-dibromo propionamido)-aniline is prepared as solution, and with sodium hydroxide adjustment pH value, treats the solution clarification, adding Sodium Nitrite mixing is subsequent use.
D, diazotization reaction
Make 4-(2 ', 3 '-dibromo propionamido)-aniline and sodium nitrite solution carry out diazotization, obtain diazonium liquid
E, coupled reaction
The diazonium liquid that condensated liquid that above-mentioned B makes and D are made carries out coupled reaction, obtains coupling product.
F, debrominate
With the solution that obtains formula (I) dyestuff after coupling product drying, the debrominate
Particularly, aforesaid method comprises the steps:
The dissolving of A, H acid
Xiang Shuizhong adds 100%H acid, stirs down and transfers pH=6.5-7 with sodium hydroxide solution, makes the material dissolution clarification, and the mass/volume concentration of adjustment solution is 4.5%.
B, condensation reaction
Adjustment H acid solution temperature to 0 ℃.0～5 ℃ of branch of holding temperature four times adds 4-carboxyl benzene sulfonyl chloride, all adjusts pH=6～6.5 with sodium hydroxide after finishing at every turn.0～5 ℃ of holding temperature was reacted 3 hours.The pH value is adjusted with sodium hydroxide in the back, and is warming up to 90 ℃, and 90～95 ℃ of holding temperatures were reacted 1 hour.Be cooled to 25 ℃, subsequent use.
C, 4-(2 ', 3 '-dibromo propionamido)-aniline dissolving
Xiang Shuizhong adds 4-(2 ', 3 '-dibromo propionamido)-aniline, adjusts pH=7～7.5 with sodium hydroxide, treats the solution clarification, adds Sodium Nitrite, and mixing is subsequent use.
D, diazotization reaction
Xiang Shuizhong adds hydrochloric acid soln.Directly with ice adjustment solution temperature to 5 ℃, guarantee pH value less than 2 at reaction soln, under the condition of the little indigo plant of potassium iodide starch paper, 5～8 ℃ of holding temperatures are with 4-(2 ', 3 '-dibromo propionamido)-aniline solution slowly adding in 1 hour consuming time.5～10 ℃ of holding temperatures were reacted 2 hours.Eliminate excessive nitrous acid with thionamic acid.
E, coupled reaction
Diazonium liquid is joined in the condensated liquid, stir.Transfer pH=7 with yellow soda ash, be warmed up to 10 ℃, 10～15 ℃ of holding temperatures are kept pH=7～7.5, react 4 hours.
F, debromination
In E step reaction solution, add direct ice and be cooled to 5～8 ℃, transfer pH value of solution=11.5～12 with liquid caustic soda simultaneously, 8～10 ℃ of reaction solution pH=11.5～12 of temperature of reaction, concentration of sodium hydroxide solution 30%;
G, neutralization reaction
F step reaction liquid is transferred to pH=6～6.5 with 30 hydrochloric acid;
H, drying
The look liquid of G step is joined in the feed liquid preheater, adjust 210 ℃ of spray tower inlet temperatures, carry out spraying drying with 95-100 ℃ temperature out.
The dye composition of method for preparing can dye to hair fibre separately or with other dyestuff is composite; When particularly dyeing hair fibre; It demonstrates good enhancing, level-dyeing property and detergency, and has good fastness aspect photostabilization, washing fastness, anti-floating property of chlorine and the perspiration resistance of dyeing articles.And the neutral qualified discharge of the dyeing waste-water of the prepared dyestuff of this method is easy, is beneficial to environmental protection.
Embodiment
The structure and the preparation method of Yellow active dye of the present invention is illustrated above, will further explains work of the present invention through embodiment below.
Embodiment 1:
Present embodiment provides the preparation method of following formula (I) compound:
Concrete preparation method is following:
The dissolving of A, H acid
In 200 ml waters, add 100%H acid 17.1 grams, stir down and transfer pH=6.5-7, make material dissolution, clarification with 30% sodium hydroxide solution.The volume of adjustment solution is 250 milliliters, and the mass/volume concentration of adjustment solution is 4.5%.
B, condensation reaction
The outer adjustment H acid solution temperature to 0 ℃ of bathing.0～5 ℃ of branch of holding temperature four times slowly adds 100%4-carboxyl benzene sulfonyl chloride 14.0 grams, and 60 minutes consuming time altogether, finish at every turn, all adjust pH=6～6.5 with 30% sodium hydroxide.0～5 ℃ of holding temperature, it is anti-to keep pH=6～6.5, answers 3 hours.The back is warming up to 90 ℃ with 30% sodium hydroxide adjustment pH=8.5, and 90～95 ℃ of holding temperatures were reacted 1 hour.Be cooled to 25 ℃, subsequent use.
C, 4-(2 ', 3 '-dibromo propionamido)-aniline dissolving
In 200 ml waters, add 100%4-(2 ', 3 '-dibromo propionamido)-aniline 20.1 grams,, treat the solution clarification, add 100% Sodium Nitrite, 3.5 grams, mixing with 30% sodium hydroxide adjustment pH=7～7.5.Subsequent use.
D, diazotization reaction
In 200ml water, add 15.2 grams, 30% hydrochloric acid soln.Directly with ice adjustment solution temperature to 5 ℃, the adjustment volume is to 300ml.Guarantee the pH value less than 2 at reaction soln, under the condition of the little indigo plant of potassium iodide starch paper, 5～8 ℃ of holding temperatures slowly added 4-(2 ', 3 '-dibromo propionamido)-aniline solution in 1 hour consuming time.5～10 ℃ of holding temperatures were reacted 2 hours.Eliminate excessive nitrous acid with thionamic acid.
E, coupled reaction
Diazonium liquid is joined in the condensated liquid, stir.Transfer pH=7 with 96% accent yellow soda ash, be warmed up to 10 ℃, 10～15 ℃ of holding temperatures are kept pH=7～7.5, react 4 hours.
F, debromination
In E step reaction solution, add direct ice and be cooled to 5～8 ℃, transfer pH value of solution=11.5～12 with liquid caustic soda simultaneously, 8～10 ℃ of reaction solution pH=11.5～12 of temperature of reaction, concentration of sodium hydroxide solution 30%;
G, neutralization reaction
F step reaction liquid is transferred to pH=6～6.5 with 30 hydrochloric acid;
H, drying
The look liquid of G step is joined in the feed liquid preheater, adjust 210 ℃ of spray tower inlet temperatures, carry out spraying drying with 95-100 ℃ temperature out.
The purple active dye for wool application performance of the present invention's preparation is as shown in the table:
The dye composition of method for preparing can dye to hair fibre separately or with other dyestuff is composite; When particularly dyeing hair fibre; It demonstrates good enhancing, level-dyeing property and detergency, and has good fastness aspect photostabilization, washing fastness, anti-floating property of chlorine and the perspiration resistance of dyeing articles.And the neutral qualified discharge of the dyeing waste-water of the prepared dyestuff of this method is easy, is beneficial to environmental protection.
Dyestuff of the present invention and dyestuff preparation method are described through concrete embodiment.Those skilled in the art can use for reference 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 all to be regarded as and are included within the scope of the present invention.
Claims (1)
1. method for preparing the compound of following formula (I):
This method comprises the steps:
The dissolving of A, H acid
With H acid dilution dissolving, with the sodium hydroxide solution neutralization, and the adjustment strength of solution,
B, condensation reaction
4-carboxyl benzene sulfonyl chloride is added the H acid solution, with carrying out condensation reaction after the sodium hydroxide adjustment pH value,
C, 4-(2 ', 3 '-dibromo propionamido)-aniline dissolving
4-(2 ', 3 '-dibromo propionamido)-aniline is prepared as solution, and with sodium hydroxide adjustment pH value, treats the solution clarification, adding Sodium Nitrite mixing is subsequent use,
D, diazotization reaction
Make 4-(2 ', 3 '-dibromo propionamido)-aniline and sodium nitrite solution carry out diazotization, obtain diazonium liquid,
E, coupled reaction
The diazonium liquid that condensated liquid that above-mentioned B makes and D are made carries out coupled reaction, obtains coupling product,
F, debrominate
With the solution that obtains formula (I) dyestuff after coupling product drying, the debrominate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910228236 CN101723863B (en) | 2009-11-16 | 2009-11-16 | Preparation method of purple active dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910228236 CN101723863B (en) | 2009-11-16 | 2009-11-16 | Preparation method of purple active dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101723863A CN101723863A (en) | 2010-06-09 |
| CN101723863B true CN101723863B (en) | 2012-09-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200910228236 Expired - Fee Related CN101723863B (en) | 2009-11-16 | 2009-11-16 | Preparation method of purple active dye |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101723863B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558592A (en) * | 1966-12-15 | 1971-01-26 | Ciba Ltd | Phenyl-azo-naphthol dyes |
| US5092903A (en) * | 1989-09-22 | 1992-03-03 | Ciba-Geigy Corporation | Process for dyeing or printing blends of cellulosic fibre materials and silk with dihalo-propionamido or halo-acryl amido reactive dyes |
| CN1918245A (en) * | 2004-02-13 | 2007-02-21 | 西巴特殊化学品控股有限公司 | Mixtures of reactive dyes and their use |
-
2009
- 2009-11-16 CN CN 200910228236 patent/CN101723863B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558592A (en) * | 1966-12-15 | 1971-01-26 | Ciba Ltd | Phenyl-azo-naphthol dyes |
| US5092903A (en) * | 1989-09-22 | 1992-03-03 | Ciba-Geigy Corporation | Process for dyeing or printing blends of cellulosic fibre materials and silk with dihalo-propionamido or halo-acryl amido reactive dyes |
| CN1918245A (en) * | 2004-02-13 | 2007-02-21 | 西巴特殊化学品控股有限公司 | Mixtures of reactive dyes and their use |
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| Publication number | Publication date |
|---|---|
| CN101723863A (en) | 2010-06-09 |
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Granted publication date: 20120905 Termination date: 20181116 |