CN101077939A - Environment-friendly type yellow or brown neutral dye and preparation method thereof - Google Patents
Environment-friendly type yellow or brown neutral dye and preparation method thereof Download PDFInfo
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- CN101077939A CN101077939A CN 200610044573 CN200610044573A CN101077939A CN 101077939 A CN101077939 A CN 101077939A CN 200610044573 CN200610044573 CN 200610044573 CN 200610044573 A CN200610044573 A CN 200610044573A CN 101077939 A CN101077939 A CN 101077939A
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Abstract
The environment friendly yellow or brown neutral dye and its preparation process features that the environment friendly yellow or brown neutral dye with different color light and excellent vividness is prepared with iron or aluminum metal ion organic complex or its mixture and through altering the structure of monoazo dye and the type or ratio of metal ions. The metal ions contained in the dye has no environmental pollution, the fabric dyed with the dye has no harm to the health of human body, and the environment friendly yellow or brown neutral dye has high fastness.
Description
Technical field:
The present invention relates to a kind of environment-friendly metal organic complex dyestuff, particularly a kind of Yellow environment-friendly or brown neutral dye and preparation method thereof.
Technical background:
As everyone knows, metallized dye results from twentieth century seventies, owing to have good light fastness and wet colour fastness, makes that such dyestuff development is very rapid.Because the metal organic complex dyestuff color development value height that adopts copper, chromium, cobalt ion to carry out complexing to obtain, 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.
Summary of the invention:
The objective of the invention is to overcome the deficiency that prior art exists, seek to provide a kind of Yellow environment-friendly or brown neutral dye, can remedy on the existing market the preparation technology's method that lacks and provide this dyestuff such dyestuff.
A kind of Yellow environment-friendly or brown neutral dye is characterized in that it is iron or the aluminum metal ion organic complex or the mixture of iron and aluminum metal ion organic complex, has following general structure
In the structural formula R1 and R2 can be respectively-H ,-NO2 ,-OH ,-CF3 ,-CN, Cl, Br ,-SO2NH2 or-CONH2, both can be identical, also can be different, R2 can be positioned at substituent ortho position on the phenyl ring, a position or contraposition; Me is iron or aluminum metal ion, or iron and aluminum metal ion mixture, when Me is Fe3+ or Al3+, or during both hybrid metal ions, n is 1, and when Me was Fe2+ and Al3+ hybrid metal ion, the n value can be calculated and be got by blended Fe2+ and Al3+ metal ion molar ratio; Iron and aluminum metal ionic mol ratio are 1 in the mixture of described iron, aluminum metal organic complex: 0.1-10.
In order to realize the preparation method of a kind of Yellow environment-friendly or brown neutral dye, the invention is characterized at first 4-replacement-2-amino-phenol is dissolved with alkali lye, join then in hydrochloric acid and the trash ice, controlled temperature is lower than 5 ℃, pH value is a strongly-acid, add sodium nitrite solution more while stirring, keeping temperature is 0-5 ℃, reacted 1-2 hour, get diazonium salt solution, will replace di-acetyl aniline and dissolve, be cooled to 5-10 ℃ with alkali lye, the diazonium salt solution of above-mentioned preparation is joined in the replacement di-acetyl aniline solution lentamente, with the pH value=9-12 of alkali lye regulator solution, fully reacted 3-4 hour, get monoazo-dyes solution, monoazo-dyes solution is warming up to 60-90 ℃, add water-soluble aluminum salt or molysite, or aluminium salt and molysite mixing solutions, regulate pH=7-10 with alkali lye, temperature keeps 60-90 ℃, reacted 3-4 hour, add sodium-chlor and saltout, reduce to room temperature, filter, dry, pulverize; Iron in described water-soluble aluminum salt and the molysite mixing solutions and aluminum metal ionic mol ratio are 1: 0.1-10; The mol ratio of described replacement di-acetyl aniline and 4-replacement-2-amino-phenol is 1: 1.
The present invention adopts water-soluble molysite or aluminium salt or both mixing solutionss to make complexing agent, by changing structure and the species of metal ion or the ratio of monoazo-dyes, can obtain the coloured light difference but good Yellow environment-friendly or the brown neutral dye of vividness.Dyestuff institute metal ion can not cause environmental pollution producing with using in the discharge of wastewater, with the fabric of this dyeing HUMAN HEALTH is not had harm, and should yellow or brown neutral dye have good vividness and good fastness ability.
Embodiment:
Below by embodiment the present invention is described.
Embodiment 1: dyestuff neutral yellow 1 synthetic
(1) diazotization of 4-sulfoamido-2-amino-phenol: the sodium hydroxide solution 12ml with 0.1mol 4-sulfoamido-2-amino-phenol water 250ml and 30% dissolves routinely.After the dissolving its adding is contained in the 200g trash ice of 30% hydrochloric acid 30ml, controlled temperature is lower than 5 ℃, and pH value is a strongly-acid.The sodium nitrite solution that under agitation with 25ml concentration is 4mol/L joins in the reaction solution, and keeping temperature is 5-10 ℃, reacts 1-2 hour, promptly gets diazonium salt solution.Reaction formula is as follows:
(2) generation of monoazo-dyes: in there-necked flask,, be cooled to 0-5 ℃ with of the sodium hydroxide solution dissolving of 0.1mol 1-di-acetyl aniline with 100ml water, 7g yellow soda ash and 10ml 30%.Diazonium salt solution was joined in the reaction solution in 1-2 hour, and the pH value=9-12 of the alkali lye regulator solution with 30% is 0-5 ℃ of fully reaction down, up to the diazonium salt completely dissolve.The reaction finish monoazo-dyes solution.Reaction formula is as follows:
(3) preparation of metallized dye: above-mentioned monoazo-dyes solution is warming up to 75 ℃, in 2 hours, drip the aluminum trichloride solution of 0.0505mol, regulate pH=7-12 with sig water, temperature keeps 75 ℃, (with the carrying out of thin-layer chromatography monitoring reaction, developping agent is an ethyl acetate: pyridine: water=6: 1: 1) up to the monoazo-dyes completely dissolve.React and finish, regulate pH=6.5-7.0 with 1mol/L hydrochloric acid, adding sodium-chlor is saltoutd and is reduced to room temperature, and suction filtration, filter cake are dry under 80 ℃, promptly get the good yellow complex dyestuff 1 of vividness.Reaction formula is as follows:
Dyeing experiment and fastness experimental result show: yellow complex dyestuff 1 has good dyeing behavior, with 2% Huang of fibre weight
1 pair of wool fabric of look complex dyestuff and polyamide fabric dye, and can obtain coloury yellow DYED FABRICS.And DYED FABRICS has good light fastness and wet colour fastness.
Embodiment 2: dyestuff neutral brown 1 synthetic
Building-up process is with embodiment 1, but complexing agent changes iron trichloride and aluminum chloride mixture into by aluminum chloride, and wherein iron aluminum metal ion molar ratio is 1: 2, then coloury brown complex dyestuff 1.Dyeing experiment and fastness experiment test result show: brown complex dyestuff 1 has good dyeing behavior, dyes with the 2 pairs of wool fabrics of 2% brown complex dyestuff and the polyamide fabric of fibre weight, can obtain coloury brown colouring fabric.And DYED FABRICS has good light fastness and wet colour fastness.
Iron, aluminum metal ionic mol ratio are 1 in the mixture of the iron among the present invention, aluminum metal organic complex: 0.1-10.
In the various embodiments described above in used 4-sulfoamido-2-amino-phenol-SO
2NH
2Can change into-H ,-OH ,-CF3 ,-CN, Cl, Br or-CONH2; The replacement chlorine of 1-chlorine di-acetyl aniline also can change into-H ,-NO2 ,-OH ,-CF3 ,-CN, Br or-CONH2, and its position of substitution can be positioned at 3 or 4 on the phenyl ring, its method and effect are similar.
Claims (2)
1. a Yellow environment-friendly or brown neutral dye is characterized in that this dyestuff is iron or the aluminum metal ion organic complex or the mixture of iron and aluminum metal ion organic complex, has following general structure:
In the structural formula R1 and R2 can be respectively-H ,-NO2 ,-OH ,-CF3 ,-CN, Cl, Br ,-SO2NH2 or-CONH2, both are identical or different; R2 is positioned at substituent ortho position on the phenyl ring, a position or contraposition; Me is iron or aluminum metal ion, or iron and aluminum metal ion mixture, when Me is Fe3+ or Al3+, or during both hybrid metal ions, n is 1, and when Me was Fe2+ and Al3+ hybrid metal ion, the n value was calculated and got by blended Fe2+ and Al3+ metal ion molar ratio; Iron and aluminum metal ionic mol ratio are 1 in the mixture of iron, aluminum metal organic complex: 0.1-10.
2. the preparation method of a Yellow environment-friendly or brown neutral dye, it is characterized in that at first 4-replacement-2-amino-phenol being dissolved with alkali lye, join then in hydrochloric acid and the trash ice, controlled temperature is lower than 5 ℃, pH value is a strongly-acid, add sodium nitrite solution more while stirring, keeping temperature is 0-5 ℃, reacted 1-2 hour, get diazonium salt solution, will replace di-acetyl aniline and dissolve, be cooled to 5-10 ℃ with alkali lye, the diazonium salt solution of above-mentioned preparation is joined in the replacement di-acetyl aniline solution lentamente, with the pH value=9-12 of alkali lye regulator solution, fully reacted 3-4 hour, get monoazo-dyes solution, monoazo-dyes solution is warming up to 60-90 ℃, add water-soluble aluminum salt or molysite, or aluminium salt and molysite mixing solutions, regulate pH=7-10 with alkali lye, temperature keeps 60-90 ℃, reacted 3-4 hour, add sodium-chlor and saltout, reduce to room temperature, filter, dry, pulverize; Iron in water-soluble aluminum salt and the molysite mixing solutions and aluminum metal ionic mol ratio are 1: 0.1-10; The mol ratio that replaces di-acetyl substituted aniline and 4-replacement-2-amino-phenol is 1: 1.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200610044573 CN101077939A (en) | 2006-05-25 | 2006-05-25 | Environment-friendly type yellow or brown neutral dye and preparation method thereof |
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| CN 200610044573 CN101077939A (en) | 2006-05-25 | 2006-05-25 | Environment-friendly type yellow or brown neutral dye and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102796400A (en) * | 2011-05-25 | 2012-11-28 | 上海雅运纺织化工股份有限公司 | Yellow azo metallized dye composition, method and application thereof |
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2006
- 2006-05-25 CN CN 200610044573 patent/CN101077939A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102796400A (en) * | 2011-05-25 | 2012-11-28 | 上海雅运纺织化工股份有限公司 | Yellow azo metallized dye composition, method and application thereof |
| CN102796400B (en) * | 2011-05-25 | 2013-12-04 | 上海雅运纺织化工股份有限公司 | Yellow azo metallized dye composition, method and application thereof |
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