CN104710835B - Red active dye and use thereof - Google Patents
Red active dye and use thereof Download PDFInfo
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Abstract
The invention belongs to the field of fine chemical engineering and relates to red active dye. The red active dye is a compound with a general structural formula (I) and in the formula, all groups are defined in the specification. The red active dye is mainly used for dyeing and printing of protein fibers, synthetic fibers, cellulose fibers and blended fabrics. After dyeing, the fabric has a gorgeous color, good level-dyeing properties, tone reappearance, very high adhesion ratio and color fixing rate, and excellent color fastness. The red active dye can satisfy environment and ecological protection market requirements on dye.
Description
Technical field
The invention belongs to field of fine chemical is and in particular to a kind of red reactive dyes and its application.
Background technology
Fypro（It is commonly called as nylon）It is the third-largest textile fabric after terylene and cotton fiber, be also synthetic fibers
Second largest kind, accounts for the 22%～30% of synthetic fibers.General Fypro dyeing dyestuff is mainly disperse dyes, acid dye
Material and premetallized dye.With these kinds of dyes institute dyeing and weaving things, fastness is not good enough, and coloured light is not gorgeous, and to environment.Enter
After entering 21 century, due to the restriction of ecological environment, for the dye-uptake of dyestuff, degree of fixation, fastness properties and dyeing waste-water
Require more and more higher, above-mentioned dyestuff can not meet the demand of era development, have impact on the development of Fypro.
At present, the large red reactive dyes kind on market is C.I. Reactive Red 2 41, and its structural formula is as follows, main use
Yu Mian, the dyeing of viscose fiber, have higher affinity and excellent level-dyeing property, degree of fixation only 70%.
In view of the premium properties of reactive dye, need the more reactive dye kinds of exploitation badly, can be allowed to be applied to more
On the material of species, and provide wider spectral range.
Content of the invention
It is an object of the invention to provide a kind of excellent performance, it is particularly suited for polyamide fiber material dyeing and stamp
Red reactive dyes compound and its application.
Technical scheme is as follows：
A kind of red reactive dyes, structure such as formula（Ⅰ）Shown：
In formula：
X is selected from Cl or F；
Y is selected from Y and is selected from-SO2CH=CH2Or-SO2CH2CH2OSO3M, Y are located at meta or para position；
R is selected from H ,-CH3Or-CH2CH3；
M is selected from H, Na, K or Li.
More preferably technical scheme is the present invention, formula（Ⅰ）Red reactive dyes in：
X is selected from Cl or F；
Y is selected from-SO2CH=CH2Or-SO2CH2CH2OSO3M, Y are located at meta or para position；
R is selected from H；
M is selected from H, Na, K or Li.
Or,
X is selected from Cl or F；
Y is selected from-SO2CH=CH2Or-SO2CH2CH2OSO3M, Y are located at meta or para position；
R is selected from-CH2CH3；
M is selected from H, Na, K or Li.
Technical scheme still more preferably is, the following red reactive dyes of structural formula, and in formula, M is selected from H or Na,
Technical scheme also includes formula（Ⅰ）The preparation method of shown red reactive dyes, in following
Hold：
Y is selected from-SO2CH2CH2OSO3The formula of M（Ⅰ）The preparation of shown red reactive dyes：
Three polychlorostyrene/fluorine cyanogen elder generation and right/m- beta-hydroxy second sulfone aniline sulfuric ester, 3-N- ethylamino phenyl (2- sulfonic acid oxygen second
Base) sulfone carries out a condensation, a condensation substance and 2,4- diamino benzene sulfonic acid sodium and carries out diazotising after two condensations, diazotising product again with
Two contracting things of three polychlorostyrene/fluorine cyanogen priority and H-acid, N-ethylaniline reaction carry out coupling, obtain hydroxyethyl sulfone sulfate type active red
Dyestuff.
When in structure, X is Cl, Cyanuric Chloride and 2,4- diamino benzene sulfonic acid sodium carry out diazotising after a condensation, Ran Houyu
Two contracting things of Cyanuric Chloride priority and H-acid, N-ethylaniline reaction carry out coupling, product and right/m- beta-hydroxy second sulfone after coupling
Aniline sulfuric ester, 3-N- ethylamino phenyl (2- sulfonic acid oxygen ethyl) sulfone are condensed, and obtain hydroxyethyl sulfone sulfate type active red
Dyestuff.
Y is selected from-SO2CH=CH2Formula（Ⅰ）The preparation of shown red reactive dyes：
Above-mentioned active red dye solution is hydrolyzed in the basic conditions and can get vinyl-sulfone reactive red.Wherein, alkali
For sodium hydroxide, sodium carbonate, potassium hydroxide etc., preferably sodium hydroxide.
Wherein three polychlorostyrene/fluorine cyanogen and right/m- beta-hydroxy second sulfone aniline sulfuric ester, 3-N- ethylamino phenyl (2- sulfonic acid oxygen
Ethyl) sulfone molar ratio be 1～1.2:1, condensation temp is -10～20 DEG C, between pH value 1～7.Preferably molar ratio
1.05～1.15：1, -5～10 DEG C of condensation temp, between pH value 1.5～4.
In two condensation reactions：One contracting thing is 1 with the molar ratio of 2,4- diamino benzene sulfonic acid sodium：0.6～1, condensation temperature
Spend for 10～50 DEG C, between pH value 3～8.Preferably molar ratio 1：0.8～1,15～40 DEG C of condensation temp, pH value 4～7 it
Between
Hydrolysising reacting temperature is 20～60 DEG C, and pH is between 8～12.25～50 DEG C of preferable reaction temperature, pH 10-12 it
Between.
Do not saltout in preparation process, product convection drying, three-waste free discharge.
Formula of the present invention（Ⅰ）Shown red reactive dyes are used for protein fibre, synthetic fibers, the dye of cellulose fibre
Normal complexion stamp.Preferred polyamide fiber.
Advantage for present invention：The red reactive dyes of the present invention are to comply with market the demand of novel product is opened
Send out, be mainly used in protein fibre, synthetic fibers, the dyeing of cellulose fibre and stamp, be particularly suited for Fypro
Material, its performance is better than dyeing on Fypro for the existing reactive dye.Formula of the present invention（Ⅰ）Shown red activity dye
Material no carcinogenic toxicity, preparation process three-waste free discharge, are a kind of novel environmental protection type dyes of structure.Through dyes of the present invention
There is after color the features such as degree of fixation is high, fastness ability is excellent, the requirement to dyeing for the market can be met, it solves gathered in the past
The problems such as nylon dyeing staining, washing fastness and wet colour fastness difference, meanwhile, also solve conventional Fypro dye
The problem of material heavy metal environmental pollution.Its high degree of fixation and excellent fastness, can meet market to dyeing and dyestuff
Environment and ecological protection requirement, meet the demand of era development.Dyestuff of the present invention, after Fypro dyeing, presents gorgeous
Beautiful redness, has good level-dyeing property and color reproducibility, very high exhaustion rate and degree of fixation, and excellent assorted jail
Degree.
Specific embodiment
Following examples are used for further illustrating the present invention.The number being directed to is parts by weight, except especially indicating
Outside the solution of concentration, all it is converted to sterling metering；Concentration unit is concentration expressed in percentage by weight.The method adopting is applied for dyestuff
It is as well known to those skilled in the art public.
Prepare formula（Ⅰ）Intermediate Cyanuric Chloride used by shown red reactive dyes, cyanuric fluoride, H-acid, N- ethyl
Aniline, 2,4- diamino benzene sulfonic acid sodium, p- beta-hydroxy second sulfone aniline sulfuric ester and other raw materials are commercially available.
In preparation process of the present invention, each step operation and charging proportioning are appreciated by those skilled in the art.
Embodiment prepared by dyestuff
Embodiment 1
Preparation such as following formula dyestuff：
A) Cyanuric Chloride and H-acid primary condensation reaction
Weigh 1.88 parts of Cyanuric Chlorides, add 18 parts of water, trash ices, pull an oar 30 minutes in 0～5 DEG C.Weigh 3.41 parts of H simultaneously
Acid, in 15 parts of water, adjusts pH=6～7 with sodium carbonate so as to be completely dissolved.By above-mentioned H-acid solution in 1 hour after making beating terminates
In interior instillation Cyanuric Chloride suspension.After completion of dropping, pH value in reaction is adjusted to 2～3 with sodium carbonate, reacts H-acid free to nothing
It is terminal.
B) consecutive condensation
Weigh 1.21 parts of N-ethylanilines to be added in above-mentioned primary condensation reaction solution, be warming up to 35～40 DEG C, carbon simultaneously
Sour sodium adjusts pH value to 5～5.5, keeps this temperature and pH value to react 4 hours about, HPLC detects to disappear to N-ethylaniline and is
For reaction end.
C) Cyanuric Chloride and the condensation of 2,4- diamino benzene sulfonic acid sodium, diazotising
Weigh 1.88 parts of Cyanuric Chlorides, add 18 parts of water, trash ices, pull an oar 30 minutes in 0～5 DEG C.Weigh 2.1 part 2 simultaneously,
4- diamino benzene sulfonic acid sodium is in 15 parts of water so as to be completely dissolved.By above-mentioned 2,4- diamino benzene sulfonic acid sodium after making beating terminates
Solution adds in Cyanuric Chloride suspension.React with this understanding, be terminal to free 2, the 4- diamino benzene sulfonic acid of nothing, obtain
Cyanuric Chloride and the condensation substance of 2,4- diamino benzene sulfonic acid sodium.
Measure 2.7 part of 30% hydrochloric acid, add in above-mentioned Cyanuric Chloride and the condensation substance of 2,4- diamino benzene sulfonic acid sodium, 0～5
At DEG C, add 0.7 part of sodium nitrite, under the conditions of being somebody's turn to do, keep hydrochloric acid and the micro- excess of nitrous acid, react 2 hours, with a small amount of ammonia
Base sulfonic acid eliminates micro- excessive nitrous acid, obtains Cyanuric Chloride and 2,4- diamino benzene sulfonic acid sodium condensation substance diazol.
D) coupling
By c）Diazol is added in two contracting things b), adjusts pH=6～7 of reaction medium at 10～15 DEG C with sodium carbonate
Carry out coupling reaction, diazol disappears and is reaction end.
E) it is condensed
Weigh 2.81 parts of p- beta-hydroxy second sulfone aniline sulfuric ester solids, be added in above-mentioned conjugates d), heat temperature raising
To 40～50 DEG C, adjust pH=6～7 of reaction medium with sodium carbonate, disappear for reaction end to detection two components.It is subsequently adding
Stabilizer, Direct spraying is dried, and obtains 17 parts of Product Activity red.
By above-mentioned dyestuff（1）Fypro dyes, obtains bright-coloured redness, dye uptake reaches 95.3%, degree of fixation
Reach 90.5%.
Dyestuff by synthesis（1）Compound, does high resolution mass spectrum, and it calculates dye molecule amount M=1142.00, surveys dyestuff
Molecular weight M=1142.08.Value of calculation is [M-1]/1=1141.00, and measured value is 1141.08；Value of calculation is [M-2]/2=570,
Measured value is 570.04；Value of calculation is [M-3]/3=379.67, and measured value is 379.69.
Dyestuff to synthesis（1）Compound carries out recrystallization purification, its hydrogen nuclear magnetic resonance modal data（1HNMR, 300MHz,
Internal standard TMS, solvent DMSO）Display is as follows：δppm9.82（1H, s, OH）, 9.44（3H, s, NH）, 7.49（1H, d, matter on naphthalene nucleus
Sub- hydrogen）, 7.19（1H, d, proton hydrogen on naphthalene nucleus）, 7.28（1H, d, proton hydrogen on naphthalene nucleus）, 7.66（On 2H, d, one substituted benzene ring
Proton hydrogen）, 7.23（Proton hydrogen on 2H, d, one substituted benzene ring）, 6.77（Proton hydrogen on 1H, d, one substituted benzene ring）, 7.86（1H,
D, proton hydrogen on trisubstituted benzene ring）, 7.81（1H, d, proton hydrogen on trisubstituted benzene ring）, 7.58（1H, d, matter on trisubstituted benzene ring
Sub- hydrogen）, 7.24（2H, d, proton hydrogen on para-position disubstituted benzenes ring）, 6.69（2H, d, proton hydrogen on para-position disubstituted benzenes ring）,
4.09（2H, m, CH2OSO3Na）, 3.6（2H, m, SO2CH2）, 3.1（2H, m, CH2）, 1.15（3H, q, CH3）.
Embodiment 2,3：
With the method described in similar embodiment 1, select m- beta-hydroxy second sulfone aniline sulfuric ester and 3-N- ethyl ammonia respectively
Base phenyl (2- sulfonic acid oxygen ethyl) sulfone replaces p- beta-hydroxy second sulfone aniline sulfuric ester for raw material, can obtain dye as follows
Material 2 and dyestuff 3：
Embodiment 4：
Preparation such as following formula dyestuff：
By e in embodiment 1）The condensation solution obtaining, i.e. dyestuff（1）Solution, adjusts pH=10 with sodium hydroxide, and keeps
Temperature is reacted at 40～50 DEG C, is followed the tracks of reaction and is disappeared to condensation substance with HPLC and terminates.Adjust pH=7.0 with 30% hydrochloric acid solution again,
17.5 parts such as above formula dyestuff are obtained after directly drying（4）Red reactive dyes product.
By above-mentioned dyestuff（4）Fypro dyes, obtains bright-coloured redness, dye uptake reaches 98.1%, degree of fixation
Reach 92.3%.
Dyestuff by synthesis（4）Compound, does high resolution mass spectrum, and it calculates dye molecule amount M=1044.04, surveys dyestuff
Molecular weight 1044.10.Value of calculation is [M-1]/1=1043.04, and measured value is 1043.10；Value of calculation is [M-2]/2=521.02,
Measured value is 521.05.
Dyestuff to synthesis（4）Compound carries out recrystallization purification, its hydrogen nuclear magnetic resonance modal data（1HNMR, 300MHz,
Internal standard TMS, solvent DMSO）Display is as follows：δppm9.82（1H, s, OH）, 9.44（3H, s, NH）, 7.49（1H, d, matter on naphthalene nucleus
Sub- hydrogen）, 7.19（1H, d, proton hydrogen on naphthalene nucleus）, 7.28（1H, d, proton hydrogen on naphthalene nucleus）, 7.66（On 2H, d, one substituted benzene ring
Proton hydrogen）, 7.23（Proton hydrogen on 2H, d, one substituted benzene ring）, 6.77（Proton hydrogen on 1H, d, one substituted benzene ring）, 7.86（1H,
D, proton hydrogen on trisubstituted benzene ring）, 7.81（1H, d, proton hydrogen on trisubstituted benzene ring）, 7.58（1H, d, matter on trisubstituted benzene ring
Sub- hydrogen）, 7.24（2H, d, proton hydrogen on para-position disubstituted benzenes ring）, 6.69（2H, d, proton hydrogen on para-position disubstituted benzenes ring）,
6.80（1H, m, SO2CH）,6.41（1H, m, CH2Trans）, 6.18（1H, m, CH2Cis）, 3.1（2H, m, CH2）, 1.15（3H,
Q, CH3）.
Embodiment 5,6：
With the method described in similar embodiment 4, select the corresponding condensation solution of embodiment 2,3 successively through basic hydrolysiss, can
To obtain dyestuff 5 as follows and dyestuff 6：
Embodiment 7：
Preparation such as following formula dyestuff：
A) cyanuric fluoride and H-acid primary condensation reaction
Weigh 3.41 parts of H-acid, mix with 20 parts of water, after being allowed to be completely dissolved with sodium carbonate, be added drop-wise to equipped with 1.48 part three
In the airtight there-necked flask of poly- fluorine cyanogen, maintain the temperature at -5～5 DEG C.With HPLC detection, react and disappear for terminal to H-acid, obtain one
Contracting thing solution, standby.
B) consecutive condensation
Weigh 1.21 parts of N-ethylanilines to be added in above-mentioned primary condensation reaction solution, be warming up to 35～40 DEG C, carbon simultaneously
Sour sodium adjusts pH value and detects to N-ethylaniline disappearance as reaction end to 5～6, HPLC.
C) cyanuric fluoride and p- beta-hydroxy second sulfone aniline sulfuric ester one be condensed, again with 2,4- diamino benzene sulfonic acid sodium two contracting
Close
Weigh 2.81 parts of p- beta-hydroxy second sulfone aniline sulfuric ester, mix with 20 parts of water, be allowed to be completely dissolved with sodium carbonate
Afterwards, it is added drop-wise to equipped with the airtight there-necked flask of 1.48 parts of cyanuric fluorides, maintain the temperature at -5～5 DEG C.Reaction is followed the tracks of extremely with HPLC
P- beta-hydroxy second sulfone aniline sulfuric ester disappears and terminates, and obtains a contracting thing solution.It is subsequently adding 2.1 parts of 2,4- diamino benzene sulfonic acids
Sodium, heat temperature raising, 35～40 DEG C of reactions of keeping temperature, pH=6.0 reacts.Reaction is followed the tracks of to compound 2,4- diaminourea with HPLC
Benzene sulfonic acid sodium salt disappears for reaction end.
D) diazotising, coupling
Measure 2.7 part of 30% hydrochloric acid, add the nitrous acid at 0～5 DEG C, adding 0.7 part in above-mentioned two contracting things c) obtaining
Sodium, keeps hydrochloric acid and the micro- excess of nitrous acid under the conditions of being somebody's turn to do, and reacts 2 hours, eliminates micro- excessive nitrous with a small amount of sulfamic acid
Acid, obtains c) two contracting thing diazol.
Above-mentioned c) two contracting thing diazols are added in two contracting things b), at 10～15 DEG C, reaction medium are adjusted with sodium carbonate
PH=6～7 carry out coupling reaction, diazol disappears and is reaction end.It is subsequently adding stabilizer, Direct spraying is dried, and obtains 17
Part such as above formula dyestuff（7）Red reactive dyes product.
By above-mentioned dyestuff（7）Fypro dyes, obtains bright-coloured redness, dye uptake reaches 96.2%, degree of fixation
Reach 89.7%.
Embodiment 8,9：
With the method described in similar embodiment 7, select m- beta-hydroxy second sulfone aniline sulfuric ester and 3-N- ethyl ammonia respectively
Base phenyl (2- sulfonic acid oxygen ethyl) sulfone replaces p- beta-hydroxy second sulfone aniline sulfuric ester for raw material, can obtain dye as follows
Material 8 and dyestuff 9：
Embodiment 10～12：
With the method described in similar embodiment 4, select the corresponding dye solution of embodiment 7,8,9 successively through basic hydrolysiss,
Dyestuff 10～12 as follows can be obtained：
Application embodiment
Embodiment 13:
Dyestuff（1）By 1%o.w.f（Opposed fabric weight）Consumption, bath raio 1:20, it is 1g/L in acetic acid concentration, level dyeing agent concentration
Under the conditions of 1g/L, the Fypro through precooking is entered dye at room temperature, is heated up with the speed of 1 DEG C/min under continuous stirring
To 95 DEG C, insulation dyeing 60min, then cool to 60 DEG C, washing.
Dye sample again through fixation treatment, wash, dry, bright-coloured redness is presented on Fypro.There is excellent consolidating
Color rate, lifting force and every color fastness.
Red reactive dyes items application performance index prepared by embodiment 2～12 is same as the test knot of embodiment 13
Really.
Claims (10)
1. a kind of red reactive dyes it is characterised in that：The compound structure of red reactive dyes such as formula（Ⅰ）Shown：
In formula：
X is selected from Cl or F；
Y is selected from-SO2CH=CH2Or-SO2CH2CH2OSO3M, Y are located at meta or para position；
R is selected from H ,-CH3Or-CH2CH3；
M is selected from H, Na, K or Li.
2. according to the red reactive dyes described in claim 1 it is characterised in that：
Formula（Ⅰ）In compound,
X is selected from Cl or F；
Y is selected from-SO2CH=CH2Or-SO2CH2CH2OSO3M, Y are located at meta or para position；
R is selected from H；
M is selected from H, Na, K or Li.
3. according to the red reactive dyes described in claim 1 it is characterised in that：
Formula（Ⅰ）In compound,
X is selected from Cl or F；
Y is selected from-SO2CH=CH2Or-SO2CH2CH2OSO3M, Y are located at meta or para position；
R is selected from-CH2CH3；
M is selected from H, Na, K or Li.
4. according to the red reactive dyes described in claim 1,2 or 3 it is characterised in that：Formula（Ⅰ）In compound, M is selected from H
Or Na.
5. a kind of preparation method according to the red reactive dyes described in claim 1 it is characterised in that：
Y is selected from-SO2CH2CH2OSO3The formula of M（Ⅰ）The preparation of shown red reactive dyes：
Three polychlorostyrene/fluorine cyanogen elder generation and right/m- beta-hydroxy second sulfone aniline sulfuric ester, 3-N- ethylamino phenyl (2- sulfonic acid oxygen ethyl)
Sulfone carries out a condensation, a condensation substance and 2,4- diamino benzene sulfonic acid sodium and carries out diazotising after two condensations, and diazotising product is again with three
Two contracting things of polychlorostyrene/fluorine cyanogen priority and H-acid, N-ethylaniline reaction carry out coupling, obtain hydroxyethyl sulfone sulfate type active red dye
Material；
When in structure, X is Cl, Cyanuric Chloride and 2,4- diamino benzene sulfonic acid sodium carry out diazotising after a condensation, then with trimerization
Two contracting things of chlorine cyanogen priority and H-acid, N-ethylaniline reaction carry out coupling, product and right/m- beta-hydroxy second sulfone aniline after coupling
Sulfuric ester, 3-N- ethylamino phenyl (2- sulfonic acid oxygen ethyl) sulfone are condensed, and obtain hydroxyethyl sulfone sulfate type active red dye.
6. according to the red reactive dyes described in claim 5 preparation method it is characterised in that：
Above-mentioned active red dye solution is hydrolyzed in the basic conditions and can get Y selected from-SO2CH=CH2Formula（Ⅰ）Shown second
Alkene sulfone type active red dye.
7. in accordance with the method for claim 5 it is characterised in that：Described three polychlorostyrene/fluorine cyanogen and right/m- beta-hydroxy second sulfone benzene
Amine sulfuric ester, the molar ratio of 3-N- ethylamino phenyl (2- sulfonic acid oxygen ethyl) sulfone are 1～1.2:1, condensation temp is -10
～20 DEG C, between pH value 1～7.
8. in accordance with the method for claim 5 it is characterised in that：A described contracting thing is fed intake with 2,4- diamino benzene sulfonic acid sodium
Mol ratio is 1：0.6～1, condensation temp is 10～50 DEG C, pH value 3～8.
9. in accordance with the method for claim 6 it is characterised in that：Hydrolysising reacting temperature be 20～60 DEG C, pH 8～12 it
Between.
10. a kind of according to the such as formula of the structure described in claim 1（Ⅰ）It is fine that shown red reactive dyes are applied to protein
In dimension, synthetic fibers, the dyeing of cellulose fibre or stamp.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5760193A (en) * | 1995-11-15 | 1998-06-02 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Triazinyl-substituted fiber-reactive azo dyes wherein the triazinyl groups bear an N-containing substituent, and methods of using same |
| US5847090A (en) * | 1996-06-05 | 1998-12-08 | Sumitomo Chemical Company, Limited | Monoazo compounds and process for dyeing or printing fiber materials using the same |
| JP5194477B2 (en) * | 2007-02-16 | 2013-05-08 | 住友化学株式会社 | Reactive dye composition and dyeing method |
-
2013
- 2013-12-11 CN CN201310681445.6A patent/CN104710835B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5760193A (en) * | 1995-11-15 | 1998-06-02 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Triazinyl-substituted fiber-reactive azo dyes wherein the triazinyl groups bear an N-containing substituent, and methods of using same |
| US5847090A (en) * | 1996-06-05 | 1998-12-08 | Sumitomo Chemical Company, Limited | Monoazo compounds and process for dyeing or printing fiber materials using the same |
| JP5194477B2 (en) * | 2007-02-16 | 2013-05-08 | 住友化学株式会社 | Reactive dye composition and dyeing method |
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