CN106634015B - A kind of violet acid dye and preparation method thereof - Google Patents
A kind of violet acid dye and preparation method thereof Download PDFInfo
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- CN106634015B CN106634015B CN201611169130.3A CN201611169130A CN106634015B CN 106634015 B CN106634015 B CN 106634015B CN 201611169130 A CN201611169130 A CN 201611169130A CN 106634015 B CN106634015 B CN 106634015B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention relates to a kind of violet acid dyes and preparation method thereof, belong to chemical dye field.The violet acid dye is as shown in formula I.Violet acid dye of the present invention has many advantages, such as that quick permeation, bright degree are good, it is full to obtain color, can be used for the independent dyeing of protein fabric and nylon fabric.
Description
Technical field
The present invention relates to a kind of violet acid dyes and preparation method thereof, belong to chemical dye field.
Background technique
Naphthoquinones is a kind of natural organic matter for being widely present in nature, considers that 1,4-naphthoquinone, 1 can be divided into from structure,
2- naphthoquinones and 2,6- naphthoquinones three types.Wherein, most of naphthoquinones is 1,4-naphthoquinone.Since naphthoquinone compound has not
Saturated ketone structure, makes it have conjugate double bond system, when being connected with supplied for electronic conjugated radicle in its molecule, constitutes a chromogen
System.
Generally, azo and anthraquinone account for very big specific gravity to acid dyes in its chromogen structure in structure, and in addition there are three
All kinds of chromogens such as fragrant methane, azine, indigo, quinoline, phthalocyanine, xanthene and nitro-imine.
In recent years, increasing to the demand of the textiles such as wool, silk and polyamide fibre, the demand of acid dyes also day
Benefit increases, and has not been reported using naphthoquinones as chromogen as acid dyes.
Summary of the invention
The present invention is by the molecular level of 1,4-naphthoquinone, introducing a variety of groups, the violet acid dye for preparing it
Have many advantages, such as that performance is stable, solubility is high, dye-uptake is high, it is good to dye good synchronism, good level-dyeing property, color reproducibility, especially
Have the advantages that dye is dark prominent, solves the above problem.
The present invention provides a kind of violet acid dye, the violet acid dye is as shown in formula I:
Another object of the present invention is to provide a kind of preparation method of above-mentioned violet acid dye, and the preparation method includes such as
Lower step:
1. 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt, natrium carbonicum calcinatum are dissolved in water, it is cooled to 0-5 DEG C, is obtained molten
Liquid I；
2. sodium nitrite is dissolved in water, ice is added, obtains solution II；
3. solution I and solution II are mixed, concentrated hydrochloric acid is added, until being cooled to 0-5 when celadon suspended matter no longer generates
DEG C, pH value is adjusted to 5.5-6.5, obtains solution III；
4. sodium bicarbonate, 2-hydroxy-1,4-naphthoquinone are dissolved in water, it is cooled to 0-5 DEG C, obtains solution IV；
5. solution III is reacted with solution IV, it is acidified, is concentrated, recrystallization obtains violet acid dye.
1- amino-8-naphthol -3,6- disulfonic acid-sodium salt of the present invention, natrium carbonicum calcinatum, sodium nitrite, concentrated hydrochloric acid, carbon
The molar ratio of sour hydrogen sodium and 2 hydroxy 1,4 naphthoquinone (lawsone) is preferably 2:0.8-1.2:2.3-2.7:2.3-2.7:1.8-2.2:1.8-
2.2。
The weight of water is preferably 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt weight 9- in solution I of the present invention
11 times.
The weight of water is preferably 2-4 times of sodium nitrite weight in solution II of the present invention.
The weight of ice is preferably 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt weight 9- in solution II of the present invention
11 times.
The weight of water is preferably 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt weight 9- in solution IV of the present invention
11 times.
The invention has the following beneficial effects:
1. violet acid dye of the present invention has, light resistance is good, moisture-proof is good, good level-dyeing property, stability are high, biology
The advantages that active high, solubility is big；Wherein, for balance dye-uptake up to 94% or more, the dry fastness for contaminating product is 5 grades, wet friction
Fastness is 4-5 grades, fastness to perspiration is 4-5 grades, fastness to ironing is 4-5 grades, referring to 15979-2002 " disposable health
Articles sanitary standard " in method the anti-microbial property of dyestuff is tested, the results showed that it is to Escherichia coli and golden yellow grape
The biocidal property of coccus is up to 99% or more.
2. violet acid dye of the present invention has many advantages, such as that quick permeation, bright degree are good, it is full to obtain color, can be used for
The independent dyeing of protein fabric and nylon fabric.
3. violet acid dye of the present invention has good compatibility, can be used as in the dyeing of combination tone or composition
A kind of component be used together with other similar acid dyes.
Specific embodiment
Following non-limiting embodiments can with a person of ordinary skill in the art will more fully understand the present invention, but not with
Any mode limits the present invention.
Embodiment 1
A kind of preparation method of violet acid dye, the preparation method include the following steps:
1. 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt, natrium carbonicum calcinatum are add to deionized water heating for dissolving,
The weight of deionized water is 10 times of 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt weight in solution I, is cooled to 4 DEG C, obtains
Solution I；
2. sodium nitrite is dissolved in deionized water, the weight of deionized water is 3 times of sodium nitrite weight in solution II, then
Trash ice is added, the weight of trash ice is 10 times of 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt weight in solution II, obtains solution
Ⅱ；
3. solution I and solution II are mixed, concentrated hydrochloric acid is added, until being cooled to 4 when celadon suspended matter no longer generates
DEG C, pH value is adjusted to 6 using sodium bicarbonate, obtains solution III；
4. sodium bicarbonate, 2-hydroxy-1,4-naphthoquinone are add to deionized water heating for dissolving, deionized water in solution IV
Weight be 10 times of 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt weight, be cooled to 4 DEG C, obtain solution IV；
It reacts 5. solution III is added in solution IV, is acidified using hydrochloric acid, is concentrated, recrystallization, obtained purple acid
Dyestuff is as shown in formula I, above-mentioned 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt, natrium carbonicum calcinatum, sodium nitrite, concentrated hydrochloric acid, carbon
The molar ratio of sour hydrogen sodium and 2 hydroxy 1,4 naphthoquinone (lawsone) is 2:1:2.5:2.5:2:2；
Application examples 1
A method of dyeing wool on the violet acid dye prepared using embodiment 1:
Its formula for dye liquor is as follows:
Violet acid dye 1.5% (to wool heavy)
It crystallizes anhydrous sodium sulphate 10% (to wool heavy)
Peregal 0.5% (to wool heavy)；
Its colouring method is as follows:
Wool is entered into dye in 50 DEG C, dyeing pH value is 4.5, bath raio 1:30,70 DEG C are warming up to the rate of 1 DEG C/1.5min,
Boiling is warming up to the rate of 1 DEG C/2min again, boiling dye 60min is washed, drying.
Application examples 2
A method of contaminating polyamide fibre on the violet acid dye prepared using embodiment 1:
Its formula for dye liquor is as follows:
Violet acid dye 2.5% (to polyamide fibre weight)
Glacial acetic acid 0.5ml/L
Peregal 1g/L；
Its colouring method is as follows:
Peregal and acetic acid is first added, is warming up to 40 DEG C, adds polyamide fibre processing 10min, purple acid dye is then added
Material, bath raio 1:30 are warming up to boiling, boiling dye 60min, washing, fixation with the rate of 1 DEG C/2min；
Its fixation formula is as follows:
Tannic acid 2% (to polyamide fibre weight)
Glacial acetic acid 2% (to polyamide fibre weight)
Tartar emetic 1% (to polyamide fibre weight)；
Its color-fixing method is as follows:
50 DEG C are first added tannic acid and glacial acetic acid, 70 DEG C of constant temperature 20min, add tartar emetic, bath raio 1:30,75 DEG C of constant temperature
20min, cleaning.
Application examples 3
A method of contaminating silk on the violet acid dye prepared using embodiment 1:
Its formula for dye liquor is as follows:
Violet acid dye 2.5% (to silk weight)
Peregal 1g/L；
Its colouring method is as follows:
Silk is entered into dye in 50 DEG C, dyeing pH value is 5, bath raio 1:30,70 DEG C are warming up to the rate of 1 DEG C/1.5min, then
95 DEG C, upper dye 50min are warming up to the rate of 1 DEG C/2min, is washed, fixation.
Claims (6)
1. a kind of violet acid dye, it is characterised in that: the violet acid dye is as shown in formula I:
2. the preparation method of violet acid dye described in claim 1, it is characterised in that: the preparation method includes following step
It is rapid:
1. 1- amino-8-naphthol -3,6- disulfonic acid-sodium salt, natrium carbonicum calcinatum are dissolved in water, it is cooled to 0-5 DEG C, obtains solution I；
2. sodium nitrite is dissolved in water, ice is added, obtains solution II；
3. solution I and solution II are mixed, concentrated hydrochloric acid is added, until it is cooled to 0-5 DEG C when celadon suspended matter no longer generates,
PH value is adjusted to 5.5-6.5, obtains solution III；
4. sodium bicarbonate, 2-hydroxy-1,4-naphthoquinone are dissolved in water, it is cooled to 0-5 DEG C, obtains solution IV；
5. solution III is reacted with solution IV, 1- amino-8-naphthol -3, the 6- disulfonic acid-sodium salt, natrium carbonicum calcinatum, nitrous
Sour sodium, concentrated hydrochloric acid, sodium bicarbonate and 2 hydroxy 1,4 naphthoquinone (lawsone) molar ratio be 2:0.8-1.2:2.3-2.7:2.3-2.7:1.8-
2.2:1.8-2.2 acidification is concentrated, recrystallization obtains violet acid dye.
3. preparation method according to claim 2, it is characterised in that: the weight of water is 1- amino -8- naphthalene in the solution I
9-11 times of phenol -3,6- disulfonic acid-sodium salt weight.
4. preparation method according to claim 3, it is characterised in that: the weight of water is sodium nitrite weight in the solution II
2-4 times of amount.
5. the preparation method according to claim 4, it is characterised in that: the weight of ice is 1- amino -8- in the solution II
9-11 times of naphthols -3,6- disulfonic acid-sodium salt weight.
6. preparation method according to claim 5, it is characterised in that: the weight of water is 1- amino -8- in the solution IV
9-11 times of naphthols -3,6- disulfonic acid-sodium salt weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611169130.3A CN106634015B (en) | 2016-12-16 | 2016-12-16 | A kind of violet acid dye and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611169130.3A CN106634015B (en) | 2016-12-16 | 2016-12-16 | A kind of violet acid dye and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106634015A CN106634015A (en) | 2017-05-10 |
| CN106634015B true CN106634015B (en) | 2018-12-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611169130.3A Expired - Fee Related CN106634015B (en) | 2016-12-16 | 2016-12-16 | A kind of violet acid dye and preparation method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19937328A1 (en) * | 1998-08-11 | 2000-03-02 | Binder Gottlieb Gmbh & Co | New dyes used for dying e.g. wool, silk, polyamide or cotton are azo, anthraquinone, quinizarin, coumarin or indigo dyes with sulfonyl, e.g. sulfonyl chloride, or sulfonamide group(s) |
| CN104031408A (en) * | 2014-06-25 | 2014-09-10 | 大连工业大学 | Naphthaquinone-type brown reactive disperse dye and preparation method thereof |
-
2016
- 2016-12-16 CN CN201611169130.3A patent/CN106634015B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19937328A1 (en) * | 1998-08-11 | 2000-03-02 | Binder Gottlieb Gmbh & Co | New dyes used for dying e.g. wool, silk, polyamide or cotton are azo, anthraquinone, quinizarin, coumarin or indigo dyes with sulfonyl, e.g. sulfonyl chloride, or sulfonamide group(s) |
| CN104031408A (en) * | 2014-06-25 | 2014-09-10 | 大连工业大学 | Naphthaquinone-type brown reactive disperse dye and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| Disperse Styryl and Azo Dyes for Polyester and Nylon Fibre: Synthesis, Opticaliz Properties Having the 1,2,4-triketo Naphthoquinone Skeleton;Sharad R. Patil et al.;《Fibers and Polymers》;20151231;第16卷(第5期);第1068-1074页 * |
| Researches on Chemotherapeutic Drugs against Viruses. X. Antiviral Effects of Naphthoquinone Derivatives;Ueda Takeo et al.;《Yakugaku Zasshi》;19521231;第72卷;第1360-1363页 * |
| Visible absorption spectra of some novel heteroarylazo disperse dyes derived from 2-hydroxy-1,4-naphthoquinone";Fikret Karc et al.;《Color. Technol.》;20050307;第121卷;第153-157页 * |
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| CN106634015A (en) | 2017-05-10 |
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