CN1436817A - Environment protecting blue, violet and bluish violet neutral dyes and their prepn - Google Patents
Environment protecting blue, violet and bluish violet neutral dyes and their prepn Download PDFInfo
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- CN1436817A CN1436817A CN 02110009 CN02110009A CN1436817A CN 1436817 A CN1436817 A CN 1436817A CN 02110009 CN02110009 CN 02110009 CN 02110009 A CN02110009 A CN 02110009A CN 1436817 A CN1436817 A CN 1436817A
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Abstract
The environment protecting neutral blue, voilet and bluish violet dyes are aluminum metal complex and are prepared with water soluble aluminum salt as complexing agent and through diazotization, coupling reaction and metal complexation. The environment protection neutral dyes have bright color, no environment pollution caused by heavy metal ions and no harm to human health. The black neutral dye has high blackness and excellent fastness of dyeing. The dyes have simple synthesis process with mild reaction condition and the process is easy used in industrial production.
Description
The present invention relates to a class organic dye, particularly relate to a class environment-friendly metal organic complex dyestuff.
As everyone knows, metallized dye results from twentieth century seventies, because good light fastness and wet colour fastness are arranged, makes that such dyestuff development is very rapid.It adopts copper, chromium, cobalt ion to carry out complexing, the metal organic complex dyestuff color development value height that obtains, bright-colored, so the metal organic complex dyestuff that countries in the world produce uses water-soluble copper, chromium, cobalt salt as complexing agent mostly.But it is found that in recent years, use the fabric of the dyeing that contains copper, chromium, cobalt heavy metal ion that HUMAN HEALTH is had harm, and contain a large amount of heavy metal ion, cause serious environmental to pollute in DYE PRODUCTION and in the waste water from dyestuff of discharging in using.Therefore since late 1980s, many countries have formulated environmental regulation in succession, require to reduce the emission concentration of the waste water that contains copper, chromium, cobalt heavy metal ion, have so just limited the further production and the application of this class dyestuff.
The purpose of this invention is to provide a kind of environment protecting blue purple and bluish voilet neutral dye, it can remedy the above-mentioned deficiency of prior art.
A kind of environment protecting blue purple and bluish voilet neutral dye is characterized in that it is a kind of aluminum metal organic complex, has following general structure:
R in the structural formula
1For-H ,-NH
2,-N (R
3)
2Or-NHCOCH
3R
2For-NO
2,-CF
3,-CN ,-SO
3H ,-SO
2NH
2,-COOH ,-CONH
2R
3Be alkyl or alkoxyl group.
The synthetic method of a kind of environment protecting blue purple and bluish voilet neutral dye, it is characterized in that earlier single or blended 4-replacement-2-amino-phenol being dissolved with alkali lye, add hydrochloric acid and trash ice again, the control pH value is a strongly-acid, temperature is lower than 5 ℃, adds sodium nitrite solution fast, and keeping temperature is 0-5 ℃, reacted 1-2 hour, promptly get diazonium salt solution, diazonium salt solution was added in 1-2 hour in the good substituted naphthol of dissolving, reacted 3-4 hour, obtain monoazo-dyes or mix monoazo-dyes solution, azoic dyestuff solution is warming up to 60-90 ℃, adds Tai-Ace S 150 or aluminum trichloride solution, regulate pH=7-10 with alkali, temperature keeps 60-90 ℃, reacted 3-4 hour, and added sodium-chlor again and saltout, reduce to room temperature, filter drying.
The present invention adopts water-soluble aluminum salt to make complexing agent, by changing the structure of monoazo-dyes, has obtained respectively environment heavy metal free ionic soil, and human body is not had injury, environment protecting blue, purple and bluish voilet neutral dye that coloured light is bright-coloured.Therefore has wide prospect in industrial application.Said dyestuff synthetic method is simple, and the reaction conditions gentleness is easy to suitability for industrialized production.
Below by embodiment the present invention is described.
Embodiment 1.The diazotization of synthetic (1) .4-nitro-2-amino-phenol of the blue neutral dye of environment-friendly type aluminium complexing: routinely 0.1mol 4-nitro-2-amino-phenol is added in the reactor, the alkali lye 12ml that adds entry 250ml 30% makes it dissolving.The dissolving back adds 30% hydrochloric acid 30ml and trash ice 200g, and reaction solution is suspension, and pH value is a strongly-acid.Adding 25ml concentration fast down at 0-5 ℃ is the sodium nitrite solution of 4mol/L, and keeping temperature is 0-5 ℃, reacts 1-2 hour, promptly gets diazonium salt solution.Reaction formula is as follows:
(2). the generation of monoazo-dyes: in there-necked flask, 0.1mol substituted naphthol water 100ml, yellow soda ash 7g and 30% alkali lye 10ml are dissolved, start stirring, be cooled to 5-10 ℃.Diazonium salt solution was joined in the reactor in 1-2 hour, adjust the pH value of reaction solution between 9-11 with alkali lye.Fully reacted 3-4 hour down at 5-10 ℃, up to the diazonium salt completely dissolve.The reaction finish monoazo-dyes solution.Substituted naphthol and 4-nitro-2-amino-phenol mol ratio is 1: 1.
(3). the generation of metallized dye: above-mentioned monoazo-dyes solution is warming up to 75 ℃, adds 0.5mol/L Tai-Ace S 150 or 1.0mol/L aluminum trichloride solution.Regulate pH=7-10 with sig water, temperature keeps 75 ℃, and (the thin-layer chromatography monitoring reaction carries out, developping agent: ethyl acetate up to the monoazo-dyes completely dissolve; Pyridine: water=6: 1: 1).Reaction finishes, and transfers pH=6.5-7.0 with 1mol/L hydrochloric acid, adds sodium-chlor and saltouts, and reduces to room temperature, and suction filtration, filter cake promptly get the blue neutral dye of aluminum metal complexing in 80 ℃ of dryings.The mol ratio of aluminum ion and monoazo-dyes is 1: 2.Reaction formula is:
Dyeing experiment and fastness experimental result show: this blueness neutral dye all has good dyeing behavior to wool fabric and polyamide fabric, and DYED FABRICS has good light fastness and wet colour fastness.Example 2.Synthesizing of environment-friendly type aluminium complexing purple neutral dye
Building-up process only changes 4-nitro-2-amino-phenol of 0.1mol into 4-sulfoamido-2-amino-phenol of 0.1mol with embodiment 1, gets environment-friendly type aluminium complexing purple neutral dye.Dyeing experiment and fastness experimental result show: this purple neutral dye all has good dyeing behavior to wool fabric and polyamide fabric, and DYED FABRICS has good light fastness and wet colour fastness.Embodiment 3.Synthesizing of environment-friendly type aluminium complexing bluish voilet neutral dye
Building-up process is with example 1, and only the 4-nitro-2-amino-phenol with 0.1mol changes 4-nitro-2-amino-phenol of 0.05mol and 4-sulfoamido-2-amino-phenol of 0.05mol into, gets environment-friendly type aluminium complexing bluish voilet neutral dye.Dyeing experiment and fastness experimental result show: this dyestuff all has good dyeing behavior and good light fastness and wet colour fastness to wool fabric and polyamide fabric.
4 bit substituents in the various embodiments described above in the used 4-replacement-2-amino-phenol can be used instead-NO
2,-CF
3,-CN ,-SO
3H ,-SO
2NH
2,-COOH ,-CONH
2, the substituent R in the substituted naphthol
1Can use beta naphthal or 1-replacement-7-naphthols, its method and effect are similar.
Claims (2)
1. an environment protecting blue, purple and bluish voilet neutral dye is characterized in that it is a kind of aluminum metal complex compound, has following general structure:
R in the structural formula
1For-H ,-NH
2,-N (R
3)
2Or-NHCOCH
3R
2For-NO
2,-CF
3,-CN ,-SO
3H ,-SO
2NH
2,-COOH ,-CONH
2R
3Be alkyl or alkoxyl group.
2. environment protecting blue, the synthetic method of purple and bluish voilet neutral dye, it is characterized in that earlier single or blended 4-replacement-2-amino-phenol being dissolved with alkali lye, add hydrochloric acid and trash ice again, the control pH value is a strongly-acid, temperature is lower than 5 ℃, adds sodium nitrite solution fast, and keeping temperature is 0-5 ℃, reacted 1-2 hour, promptly get diazonium salt solution, diazonium salt solution was added in 1-2 hour with alkali lye dissolve in the good substituted naphthol, reacted 3-4 hour, obtain monoazo-dyes or mix monoazo-dyes solution, azoic dyestuff solution is warming up to 60-90 ℃, adds Tai-Ace S 150 or aluminum trichloride solution, regulate pH=7-10 with alkali, temperature keeps 60-90 ℃, reacted 3-5 hour, and added sodium-chlor again and saltout, reduce to room temperature, filter drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021100098A CN1186398C (en) | 2002-02-06 | 2002-02-06 | Environment protecting blue, violet and bluish violet neutral dyes and their prepn |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021100098A CN1186398C (en) | 2002-02-06 | 2002-02-06 | Environment protecting blue, violet and bluish violet neutral dyes and their prepn |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1436817A true CN1436817A (en) | 2003-08-20 |
| CN1186398C CN1186398C (en) | 2005-01-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021100098A Expired - Fee Related CN1186398C (en) | 2002-02-06 | 2002-02-06 | Environment protecting blue, violet and bluish violet neutral dyes and their prepn |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1301990C (en) * | 2004-03-12 | 2007-02-28 | 美国永光公司 | Environmental protection reactive dyeing and use thereof |
-
2002
- 2002-02-06 CN CNB021100098A patent/CN1186398C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1301990C (en) * | 2004-03-12 | 2007-02-28 | 美国永光公司 | Environmental protection reactive dyeing and use thereof |
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| CN1186398C (en) | 2005-01-26 |
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