CN104710835A - 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, be specifically related to a kind of red reactive dyes and application thereof.
Background technology
Tynex (being commonly called as nylon) is the third-largest textile fibres after terylene and cotton fibre, is also the second largest kind of synthon, accounts for 22% ~ 30% of synthon.General tynex dyeing dyestuff mainly dispersed dye, matching stain and metallized 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.After entering 21 century, due to the restriction of ecotope, the requirement for the dye uptake of dyestuff, degree of fixation, fastness properties and dyeing waste-water is more and more higher, and above-mentioned dyestuff can not meet the demand of era development, have impact on the development of tynex.
At present, the large red reactive dyes kind on market is C.I. Reactive Red 2 41, and its structural formula is as follows, is mainly used in the dyeing of cotton, viscose fiber, has higher avidity and excellent level-dyeing property, degree of fixation only 70%.
In view of the premium properties of reactive dyestuffs, need the more reactive dyestuffs kind of exploitation badly, can make it to be applied on a greater variety of material, and spectral range is widely provided.
Summary of the invention
The object of the present invention is to provide a kind of excellent performance, be particularly useful for red reactive dyes compound and the application thereof of polyamide fiber material dyeing and stamp.
Technical scheme of the present invention is as follows:
A kind of red reactive dyes, structure is as shown in logical formula I:
In formula:
X is selected from Cl or F;
Y is selected from Y and is selected from-SO
2cH=CH
2or-SO
2cH
2cH
2oSO
3position or contraposition between M, Y are positioned at;
R is selected from H ,-CH
3or-CH
2cH
3;
M is selected from H, Na, K or Li.
The present invention more preferably technical scheme is, in the red reactive dyes of logical formula I:
X is selected from Cl or F;
Y is selected from-SO
2cH=CH
2or-SO
2cH
2cH
2oSO
3position or contraposition between M, Y are positioned at;
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-SO
2cH=CH
2or-SO
2cH
2cH
2oSO
3position or contraposition between M, Y are positioned at;
R is selected from-CH
2cH
3;
M is selected from H, Na, K or Li.
Further preferred technical scheme is, the red reactive dyes that structural formula is following, and in formula, M is selected from H or Na,
Technical scheme of the present invention also comprises the preparation method of the red reactive dyes shown in logical formula I, comprises following content:
Y is selected from-SO
2cH
2cH
2oSO
3the preparation of red reactive dyes shown in the logical formula I of M:
Three polychlorostyrene/fluorine cyanogen first carries out a condensation, a condenses and 2 with right/m-beta-hydroxy second sulfone aniline sulfuric ester, 3-N-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone, 4-diamino benzene sulfonic acid sodium carries out diazotization after two condensations, the two contracting things that diazotization product reacts with three polychlorostyrene/fluorine cyanogen priority and H acid, N-ethylaniline again carry out coupling, obtain hydroxyethyl sulfone sulfate type active red dye.
When X in structure is Cl, cyanuric chloride and 2,4-diamino benzene sulfonic acid sodium carries out diazotization after a condensation, then the two contracting things reacted with cyanuric chloride priority and H acid, N-ethylaniline carry out coupling, coupling after product and right/m-beta-hydroxy second sulfone aniline sulfuric ester, 3-N-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone carry out condensation, obtain hydroxyethyl sulfone sulfate type active red dye.
Y is selected from-SO
2cH=CH
2logical formula I shown in the preparation of red reactive dyes:
Above-mentioned active red dye solution is hydrolyzed in the basic conditions and can obtains vinyl-sulfone reactive red.Wherein, alkali is sodium hydroxide, sodium carbonate, potassium hydroxide etc., preferred sodium hydroxide.
The molar ratio of 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 is 1 ~ 1.2:1, and condensation temp is-10 ~ 20 DEG C, between pH value 1 ~ 7.Preferred molar ratio 1.05 ~ 1.15:1, condensation temp-5 ~ 10 DEG C, between pH value 1.5 ~ 4.
In two condensation reactions: the molar ratio of a contracting thing and 2,4-diamino benzene sulfonic acid sodium is 1:0.6 ~ 1, and condensation temp is 10 ~ 50 DEG C, between pH value 3 ~ 8.Preferred molar ratio 1:0.8 ~ 1, condensation temp 15 ~ 40 DEG C, between pH value 4 ~ 7
Hydrolysising reacting temperature is 20 ~ 60 DEG C, and pH is between 8 ~ 12.Preferable reaction temperature 25 ~ 50 DEG C, pH is between 10-12.
Do not saltout in preparation process, product convection drying, three-waste free discharge.
The present invention leads to the red reactive dyes shown in formula I for the dyeing of protein fibre, synthon, cellulosic fibre and stamp.Preferred polyamide fiber.
The advantage that the present invention has: red reactive dyes of the present invention complies with the demand of market to novel product to develop, be mainly used in protein fibre, synthon, the dyeing of cellulosic fibre and stamp, be particularly useful for polyamide fiber material, its performance is better than the dyeing of existing reactive dyestuffs on tynex.The present invention leads to the red reactive dyes shown in formula I without carcinogenic toxicity, preparation process three-waste free discharge, is a kind of environmental protection type dye of novel structure.There is the features such as degree of fixation is high, fastness ability is excellent after dyeing of the present invention, the requirement of market to dyeing can be met, it solve the problems such as the staining of tynex dyeing in the past, washing fastness and wet colour fastness difference, meanwhile, the problem of tynex dyestuff heavy metal environmental pollution in the past is also solved.Its high degree of fixation and excellent fastness, can meet market to dyeing and the environment of dyestuff and the requirement of ecological protection, meet the demand of era development.Dyestuff of the present invention, after tynex dyeing, presents gorgeous redness, has good level-dyeing property and color reproducibility, very high exhaustion rate and degree of fixation, and each colour fastness of excellence.
Embodiment
Following examples are used for further illustrating the present invention.The number wherein related to is parts by weight, except indicating the solution of concentration especially, is all converted to sterling metering; Concentration unit is concentration expressed in percentage by weight.The method adopted for the application of dyestuff is as well known to those skilled in the art public.
Preparing logical red reactive dyes shown in formula I intermediate cyanuric chloride used, cyanuric fluoride, H acid, N-ethylaniline, 2,4-diamino benzene sulfonic acid sodium, p-beta-hydroxy second sulfone aniline sulfuric ester and other raw materials all has commercially available.
In preparation process of the present invention, each step operation and reinforced proportioning are appreciated by those skilled in the art.
Preparation of dyestuff embodiment
Embodiment 1
Be prepared as follows formula dyestuff:
A) cyanuric chloride and H acid primary condensation reaction
Take 1.88 parts of cyanuric chlorides, add 18 parts of water, trash ices, in 0 ~ 5 DEG C of making beating 30 minutes.Take 3.41 parts of H acid simultaneously in 15 parts of water, adjust pH=6 ~ 7 with sodium carbonate, make it dissolve completely.After making beating terminates, above-mentioned H acid solution was instilled in cyanuric chloride suspension in 1 hour.After dropwising, regulate pH value in reaction to 2 ~ 3 with sodium carbonate, reaction is terminal to without free H acid.
B) consecutive condensation
Taking 1.21 parts of N-ethylanilines joins in above-mentioned primary condensation reaction solution, is warming up to 35 ~ 40 DEG C, sodium carbonate adjust ph to 5 ~ 5.5 simultaneously, keeps this temperature and pH value to react 4 hours, and HPLC detection disappears to N-ethylaniline and is reaction end.
C) cyanuric chloride and the condensation of 2,4-diamino benzene sulfonic acid sodium, diazotization
Take 1.88 parts of cyanuric chlorides, add 18 parts of water, trash ices, in 0 ~ 5 DEG C of making beating 30 minutes.Take 2.1 part of 2,4-diamino benzene sulfonic acid sodium simultaneously in 15 parts of water, make it dissolve completely.After making beating terminates, above-mentioned 2,4-diamino benzene sulfonic acid sodium solutions are added in cyanuric chloride suspension.React with this understanding, be terminal to without 2,4-free diamino benzene sulfonic acids, obtain the condenses of cyanuric chloride and 2,4-diamino benzene sulfonic acid sodium.
Measure 2.7 part of 30% hydrochloric acid, add above-mentioned cyanuric chloride and 2, in the condenses of 4-diamino benzene sulfonic acid sodium, at 0 ~ 5 DEG C, add the Sodium Nitrite of 0.7 part, keep under this condition hydrochloric acid and nitrous acid micro-excessive, react 2 hours, eliminate micro-excessive nitrous acid with a small amount of thionamic acid, obtain cyanuric chloride and 2,4-diamino benzene sulfonic acid sodium condenses diazonium salt.
D) coupling
Join in two contracting things b) by c) diazonium salt, regulate pH=6 ~ 7 of reaction medium to carry out coupled reaction at 10 ~ 15 DEG C with sodium carbonate, diazonium salt disappears and is reaction end.
E) condensation
Taking 2.81 parts of p-beta-hydroxy second sulfone aniline sulfuric ester solids, join in above-mentioned conjugates d), be heated to 40 ~ 50 DEG C, regulate pH=6 ~ 7 of reaction medium with sodium carbonate, disappearing for reaction end to detecting two components.Then add stablizer, Direct spraying is dry, obtains Product Activity red 17 parts.
Dyeed on tynex by above-mentioned dyestuff (1), obtain bright-coloured redness, dye uptake reaches 95.3%, and degree of fixation reaches 90.5%.
By dyestuff (1) compound of synthesis, do high resolution mass spectrum, it calculates dye molecule amount M=1142.00, actual measurement dye molecule amount M=1142.08.Calculated value is [M-1]/1=1141.00, and measured value is 1141.08; Calculated value is [M-2]/2=570, and measured value is 570.04; Calculated value is [M-3]/3=379.67, and measured value is 379.69.
Recrystallization purification is carried out to dyestuff (1) compound of synthesis, its hydrogen nuclear magnetic resonance modal data (1HNMR, 300MHz, interior mark TMS, solvent DMSO) show below: δ ppm9.82(1H, s, OH), 9.44(3H, s, NH), 7.49(1H, d, proton hydrogen on naphthalene nucleus), 7.19(1H, d, proton hydrogen on naphthalene nucleus), 7.28(1H, d, proton hydrogen on naphthalene nucleus), 7.66(2H, d, proton hydrogen on one substituted benzene ring), 7.23(2H, d, proton hydrogen on one substituted benzene ring), 6.77(1H, d, proton hydrogen on 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, proton hydrogen on trisubstituted benzene ring), 7.24(2H, d, proton hydrogen on contraposition disubstituted benzenes ring), 6.69(2H, d, proton hydrogen on contraposition disubstituted benzenes ring), 4.09(2H, m, CH
2oSO
3na), 3.6(2H, m, SO
2cH
2), 3.1(2H, m, CH
2), 1.15(3H, q, CH
3).
Embodiment 2,3:
With the method described in similar embodiment 1, select m-beta-hydroxy second sulfone aniline sulfuric ester and 3-N-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone to be that raw material replaces p-beta-hydroxy second sulfone aniline sulfuric ester respectively, dyestuff 2 as follows and dyestuff 3 can be obtained:
Embodiment 4:
Be prepared as follows formula dyestuff:
By condensation solution e) obtained in embodiment 1, namely dyestuff (1) solution, regulates pH=10 with sodium hydroxide, and maintains the temperature at 40 ~ 50 DEG C of reactions, follows the tracks of reaction terminate to condenses disappearance with HPLC.Regulate pH=7.0 with 30% hydrochloric acid soln again, after directly drying, obtain 17.5 parts of red reactive dyes products as above formula dyestuff (4).
Dyeed on tynex by above-mentioned dyestuff (4), obtain bright-coloured redness, dye uptake reaches 98.1%, and degree of fixation reaches 92.3%.
By dyestuff (4) compound of synthesis, do high resolution mass spectrum, it calculates dye molecule amount M=1044.04, actual measurement dye molecule amount 1044.10.Calculated value is [M-1]/1=1043.04, and measured value is 1043.10; Calculated value is [M-2]/2=521.02, and measured value is 521.05.
Recrystallization purification is carried out to dyestuff (4) compound of synthesis, its hydrogen nuclear magnetic resonance modal data (1HNMR, 300MHz, interior mark TMS, solvent DMSO) show below: δ ppm9.82(1H, s, OH), 9.44(3H, s, NH), 7.49(1H, d, proton hydrogen on naphthalene nucleus), 7.19(1H, d, proton hydrogen on naphthalene nucleus), 7.28(1H, d, proton hydrogen on naphthalene nucleus), 7.66(2H, d, proton hydrogen on one substituted benzene ring), 7.23(2H, d, proton hydrogen on one substituted benzene ring), 6.77(1H, d, proton hydrogen on 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, proton hydrogen on trisubstituted benzene ring), 7.24(2H, d, proton hydrogen on contraposition disubstituted benzenes ring), 6.69(2H, d, proton hydrogen on contraposition disubstituted benzenes ring), 6.80(1H, m, SO
2cH), 6.41(1H, m, CH
2trans), 6.18(1H, m, CH
2cis), 3.1(2H, m, CH
2), 1.15(3H, q, CH
3).
Embodiment 5,6:
With the method described in similar embodiment 4, select the corresponding condensation solution of embodiment 2,3 through basic hydrolysis successively, dyestuff 5 as follows and dyestuff 6 can be obtained:
Embodiment 7:
Be prepared as follows formula dyestuff:
A) cyanuric fluoride and H acid primary condensation reaction
Take H acid 3.41 parts, mix with 20 parts of water, after making it to dissolve completely with sodium carbonate, be added drop-wise to and be equipped with in the airtight there-necked flask of 1.48 parts of cyanuric fluorides, maintain the temperature at-5 ~ 5 DEG C.Detect with HPLC, react and disappear for terminal to H acid, obtain a contracting thing solution, for subsequent use.
B) consecutive condensation
Taking 1.21 parts of N-ethylanilines joins in above-mentioned primary condensation reaction solution, is warming up to 35 ~ 40 DEG C, sodium carbonate adjust ph to 5 ~ 6 simultaneously, and HPLC detection disappears to N-ethylaniline and is reaction end.
C) cyanuric fluoride and the condensation of p-beta-hydroxy second sulfone aniline sulfuric ester one, again with the condensation of 2,4-diamino benzene sulfonic acid sodium two
Take p-beta-hydroxy second sulfone aniline sulfuric ester 2.81 parts, mix with 20 parts of water, after making it to dissolve completely with sodium carbonate, be added drop-wise to and be equipped with in the airtight there-necked flask of 1.48 parts of cyanuric fluorides, maintain the temperature at-5 ~ 5 DEG C.Follow the tracks of reaction with HPLC to terminate to p-beta-hydroxy second sulfone aniline sulfuric ester disappearance, obtain a contracting thing solution.Then add 2.1 part of 2,4-diamino benzene sulfonic acid sodium, heat temperature raising, keep temperature 35 ~ 40 DEG C reaction, pH=6.0 reacts.Follow the tracks of reaction to compound 2,4-diamino benzene sulfonic acid sodium with HPLC to disappear for reaction end.
D) diazotization, coupling
Measure 2.7 part of 30% hydrochloric acid, add in above-mentioned two contracting things c) obtained, at 0 ~ 5 DEG C, add the Sodium Nitrite of 0.7 part, keep under this condition hydrochloric acid and nitrous acid micro-excessive, react 2 hours, eliminate micro-excessive nitrous acid with a small amount of thionamic acid, obtain c) two contracting thing diazonium salts.
Join in two contracting things b) by above-mentioned c) two contracting thing diazonium salts, regulate pH=6 ~ 7 of reaction medium to carry out coupled reaction at 10 ~ 15 DEG C with sodium carbonate, diazonium salt disappears and is reaction end.Then add stablizer, Direct spraying is dry, obtains 17 parts of red reactive dyes products as above formula dyestuff (7).
Dyeed on tynex by above-mentioned dyestuff (7), obtain bright-coloured redness, dye uptake reaches 96.2%, and degree of fixation reaches 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-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone to be that raw material replaces p-beta-hydroxy second sulfone aniline sulfuric ester respectively, dyestuff 8 as follows and dyestuff 9 can be obtained:
Embodiment 10 ~ 12:
With the method described in similar embodiment 4, select the corresponding dye solution of embodiment 7,8,9 through basic hydrolysis successively, dyestuff 10 ~ 12 as follows can be obtained:
Application embodiment
Embodiment 13:
Dyestuff (1) is by 1%o.w.f(opposed fabric weight) consumption; bath raio 1:20; be 1g/L at acetic acid concentration; levelling agent concentration is under 1g/L condition; the tynex through precooking being entered dye under room temperature, being warming up to 95 DEG C with the speed of 1 DEG C/min under continuous stirring, insulation dyeing 60min; then cool to 60 DEG C, washing.
Dye sample again through fixation treatment, wash, dry, tynex presents bright-coloured redness.There is excellent degree of fixation, lifting force and every colour fastness.
The every application performance index of red reactive dyes prepared by embodiment 2 ~ 12 is same as the test result of embodiment 13.
Claims (10)
1. a red reactive dyes, is characterized in that: the compound structure of red reactive dyes is as shown in logical formula I:
In formula:
X is selected from Cl or F;
Y is selected from-SO
2cH=CH
2or-SO
2cH
2cH
2oSO
3position or contraposition between M, Y are positioned at;
R is selected from H ,-CH
3or-CH
2cH
3;
M is selected from H, Na, K or Li.
2., according to red reactive dyes according to claim 1, it is characterized in that:
In logical formula I compound,
X is selected from Cl or F;
Y is selected from-SO
2cH=CH
2or-SO
2cH
2cH
2oSO
3position or contraposition between M, Y are positioned at;
R is selected from H;
M is selected from H, Na, K or Li.
3., according to red reactive dyes according to claim 1, it is characterized in that:
In logical formula I compound,
X is selected from Cl or F;
Y is selected from-SO
2cH=CH
2or-SO
2cH
2cH
2oSO
3position or contraposition between M, Y are positioned at;
R is selected from-CH
2cH
3;
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 characterized in that: in logical formula I compound, M is selected from H or Na.
5., according to a preparation method for red reactive dyes according to claim 1, it is characterized in that:
Y is selected from-SO
2cH
2cH
2oSO
3the preparation of red reactive dyes shown in the logical formula I of M:
Three polychlorostyrene/fluorine cyanogen first carries out a condensation, a condenses and 2 with right/m-beta-hydroxy second sulfone aniline sulfuric ester, 3-N-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone, 4-diamino benzene sulfonic acid sodium carries out diazotization after two condensations, the two contracting things that diazotization product reacts with three polychlorostyrene/fluorine cyanogen priority and H acid, N-ethylaniline again carry out coupling, obtain hydroxyethyl sulfone sulfate type active red dye;
When X in structure is Cl, cyanuric chloride and 2,4-diamino benzene sulfonic acid sodium carries out diazotization after a condensation, then the two contracting things reacted with cyanuric chloride priority and H acid, N-ethylaniline carry out coupling, coupling after product and right/m-beta-hydroxy second sulfone aniline sulfuric ester, 3-N-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone carry out condensation, obtain hydroxyethyl sulfone sulfate type active red dye.
6., according to the preparation method of red reactive dyes according to claim 5, it is characterized in that:
Above-mentioned active red dye solution is hydrolyzed in the basic conditions and can obtains Y and be selected from-SO
2cH=CH
2the vinyl-sulfone reactive red shown in logical formula I.
7. in accordance with the method for claim 5, it is characterized in that: the molar ratio of described three polychlorostyrene/fluorine cyanogen and right/m-beta-hydroxy second sulfone aniline sulfuric ester, 3-N-ethylamino phenyl (2-sulfonic acid oxygen ethyl) sulfone is 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 characterized in that: the molar ratio of a described contracting thing and 2,4-diamino benzene sulfonic acid sodium is 1:0.6 ~ 1, and condensation temp is 10 ~ 50 DEG C, pH value 3 ~ 8.
9. in accordance with the method for claim 6, it is characterized in that: hydrolysising reacting temperature is 20 ~ 60 DEG C, and pH is between 8 ~ 12.
10. one kind is applied in protein fibre, synthon, the dyeing of cellulosic fibre or stamp according to the red reactive dyes of structure according to claim 1 as shown in logical formula I.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105440728A (en) * | 2015-12-02 | 2016-03-30 | 天津德凯化工股份有限公司 | Red reactive dye and preparation method thereof |
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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105440728A (en) * | 2015-12-02 | 2016-03-30 | 天津德凯化工股份有限公司 | Red reactive dye and preparation method thereof |
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