CN105566945A - Yellow active dye and preparation and application thereof - Google Patents

Yellow active dye and preparation and application thereof Download PDF

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Publication number
CN105566945A
CN105566945A CN201410543435.0A CN201410543435A CN105566945A CN 105566945 A CN105566945 A CN 105566945A CN 201410543435 A CN201410543435 A CN 201410543435A CN 105566945 A CN105566945 A CN 105566945A
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China
Prior art keywords
active dye
och
yellow active
yellow
dyeing
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CN201410543435.0A
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徐飒英
尚庆梅
宋志承
范中伟
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Shenyang Research Institute of Chemical Industry Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
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Priority to CN201410543435.0A priority Critical patent/CN105566945A/en
Publication of CN105566945A publication Critical patent/CN105566945A/en
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Abstract

The invention belongs to the field of fine chemical engineering, and relates to a yellow active dye and preparation and an application thereof. The yellow active dye is a compound having the structure represented by the following general formula (I), wherein in the formula, all groups are defined in the specification. The yellow active dye is mainly used for dyeing and printing of protein fibers, synthetic fibers, cellulose fibers and blended fabrics. After dyeing, a fabric has the advantages of gorgeous color and luster, good level-dyeing properties, tone reappearance, and high complete absorption ratio and color fixing rate. The yellow active dye can satisfy environment and ecological protection market requirements on dyes.

Description

A kind of Yellow active dye and Synthesis and applications thereof
Technical field
The invention belongs to field of fine chemical, be specifically related to a kind of Yellow active dye and Synthesis and applications 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, there is C.I. reactive yellow 39 in market at the Yellow active dye produced, and its structural formula is as follows, is mainly used in wool, the dyeing of silk fiber and stamp, has very high dye uptake, degree of fixation and good performance.But because containing bromine in its structure, aborning to environment, and price comparison is expensive.
And other the dyeing being all mainly used in cellulosic fibre at product Yellow active dye, such as, large Yellow reactive dyes on market is C.I. REACTIVE Yellow 145, and its structural formula is as follows:
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 Yellow active dye and the Synthesis and applications thereof that are applicable to polyamide fiber material dyeing and stamp.
Technical scheme of the present invention is as follows:
A kind of Yellow active dye, structure is as shown in logical formula I:
In formula:
R 1be selected from H ,-OCH 3or-SO 3m;
R 2be selected from H ,-CH 3or-OCH 3;
Y is selected from-3-SO 2cH=CH 2or-4-SO 2cH=CH 2;
M is selected from H, Na, K or Li.
Or,
In formula:
R 1be selected from-OCH 3;
R 2be selected from SO 2cH=CH 2;
M is selected from H, Na, K or Li.
Herein, Y does not indicate concrete substituting group, is H.
The present invention more preferably technical scheme is, in logical formula I:
R 1be selected from H ,-OCH 3or-SO 3m;
R 2be selected from H ,-CH 3or-OCH 3;
Y is selected from-4-SO 2cH=CH 2;
M is selected from H, Na, K or Li.
Or,
R 1be selected from H or-OCH 3;
R 2be selected from H;
Y is selected from-3-SO 2cH=CH 2;
M is selected from H, Na, K or Li.
Or,
In logical formula I compound,
R 1be selected from-OCH 3;
R 2be selected from SO 2cH=CH 2;
M is selected from H, Na, K or Li.
Further preferred technical scheme is, the Yellow active dye 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 Yellow active dye shown in logical formula I, comprises following content:
By 1-(2,5-bis-chloro-4-sulfonic group phenyl)-3-methyl-5-pyrazolone is as coupling component, be hydrolyzed with the diazo component needed for preparation target dyestuff the vinyl-sulfone reactive yellow dye obtained as shown in logical formula I in the basic conditions by the solution that diazotization, coupled reaction obtain, wherein, alkali is sodium hydroxide, sodium carbonate, potassium hydroxide etc., preferred sodium hydroxide.
Wherein 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.
The present invention leads to the Yellow active dye 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: Yellow active dye 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 Yellow active dye shown in formula I without carcinogenic toxicity, and preparation process is not saltoutd, product convection drying, 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, solve the problem of tynex dyestuff heavy metal environmental pollution in the past.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 yellow, 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.
Prepare logical Yellow active dye shown in formula I intermediate 1-(2,5-bis-chloro-4-sulfonic group phenyl)-3-methyl-5-pyrazolone used, all have commercially available to ()-beta-hydroxy second sulfone aniline sulfuric ester and other raw materials.
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:
Getting 2.81 parts of (4-beta-hydroxyethyl sulfone sulfate) aniline is scattered in 20 parts of water, pulls an oar 1 hour, then adds 1.5 part of 30% hydrochloric acid, be cooled to 0 ~ 5 DEG C, add 0.7 part of Sodium Nitrite fast, control temperature at 0 ~ 5 DEG C, diazotization reaction 2 hours.Afterwards, eliminate excessive nitrous acid, joined consoluet 1-(2 again, 5-bis-chloro-4-sulfonic group phenyl) in-3-methyl-5-pyrazolone solution (by 3.23 parts of 1-(2,5-bis-chloro-4-sulfonic group phenyl)-3-methyl-5-pyrazolone is scattered in 30 parts of water, with the pH to 7 of sodium carbonate regulating solution, make material dissolution).Vigorous stirring, regulates the pH to 6 of reaction solution with sodium carbonate.Maintain temperature of reaction 10-15 DEG C, pH is between 6-7 in reaction, reacts after 2 hours, detects with HPLC, until two components disappear.Then, regulate pH=10 with sodium hydroxide, and maintain the temperature at 40 ~ 50 DEG C of reactions, follow the tracks of reaction with HPLC and terminate to conjugates disappearance.Regulate pH=7.0 with 30% hydrochloric acid soln again, after directly drying, obtain 9.54 parts of Yellow active dye products as above formula dyestuff (1).Its maximum absorption wavelength is λ max=389nm.
Dyeed on tynex by above-mentioned dyestuff (1), obtain bright-coloured yellow, dye uptake reaches 96.1%, and degree of fixation reaches 89.3%.
By dyestuff (1) compound of synthesis, do high resolution mass spectrum, it calculates dye molecule amount M=519.97, actual measurement dye molecule amount M=519.97.Calculated value is [M-1]/1=514.97, and measured value is 514.98.
Recrystallization purification is carried out, its hydrogen nuclear magnetic resonance modal data (1HNMR, 300MHz, interior mark TMS to dyestuff (1) compound of synthesis, solvent DMSO) show below: δ ppm8.21 (1H, s, proton hydrogen on four substituted benzene rings), 8.15 (1H, s, proton hydrogen on four substituted benzene rings), 7.86 (2H, d, proton hydrogen on disubstituted benzenes ring), 7.83 (2H, d, proton hydrogen on disubstituted benzenes ring), 6.80 (1H, m, SO 2cH), 6.41 (1H, m, CH 2trans position proton hydrogen), 6.18 (1H, m, CH 2cis position proton hydrogen), 2.40 (1H, s, proton hydrogen on pyrazole ring), 2.0 (1H, s, SO 3h), 1.94 (3H, s, CH 3).
Embodiment 2-7:
With the method described in similar embodiment 1, select (the 4-beta-hydroxyethyl sulfone sulfate) aniline in different diazo component (see table 1) replacement embodiments 1, preparation method is with embodiment 1, obtain dyestuff (2)-dyestuff (7), its concrete structure, maximum absorption wavelength and dye uptake, degree of fixation are in table 2.
The diazo component of dyestuff (2)-dyestuff (7) prepared by table 1
Dyestuff is numbered Diazo component
2 (4-beta-hydroxyethyl sulfone sulfate) aniline-2-methoxyl group
3 (4-beta-hydroxyethyl sulfone sulfate) aniline-2-methoxyl group-5-methyl
4 (4-beta-hydroxyethyl sulfone sulfate) aniline-2,5-dimethoxy
5 (4-beta-hydroxyethyl sulfone sulfate) aniline-2-sulfonic group
6 (3-beta-hydroxyethyl sulfone sulfate) aniline
7 (5-beta-hydroxyethyl sulfone sulfate) aniline-2-methoxyl group
Reactive dyestuffs prepared by the different diazo component of table 2
Dyestuff is numbered Y R 1 R 2 λ max(nm) Dye uptake (%) Degree of fixation (%)
2 4-SO 2CH＝CH 2 OCH 3 H 420 97.98 90.23
3 4-SO 2CH＝CH 2 OCH 3 CH 3 425 92.10 85.66
4 4-SO 2CH＝CH 2 OCH 3 OCH 3 435 92.85 81.80
5 4-SO 2CH＝CH 2 SO 3Na H 385 93.13 80.79
6 3-SO 2CH＝CH 2 H H 385 97.65 88.51
7 5-SO 2CH＝CH 2 OCH 3 H 415 96.73 87.59

Claims (5)

1. a Yellow active dye, is characterized in that: the compound structure of Yellow active dye is as shown in logical formula I:
In formula:
R 1be selected from H ,-OCH 3or-SO 3m;
R 2be selected from H ,-CH 3or-OCH 3;
Y is selected from-3-SO 2cH=CH 2or-4-SO 2cH=CH 2;
M is selected from H, Na, K or Li;
Or,
In formula:
R 1be selected from-OCH 3;
R 2be selected from SO 2cH=CH 2;
M is selected from H, Na, K or Li.
2., according to Yellow active dye according to claim 1, it is characterized in that:
In logical formula I compound,
R 1be selected from H ,-OCH 3or-SO 3m;
R 2be selected from H ,-CH 3or-OCH 3;
Y is selected from-4-SO 2cH=CH 2;
M is selected from H, Na, K or Li;
Or,
In logical formula I compound,
R 1be selected from H or-OCH 3;
R 2be selected from H;
Y is selected from-3-SO 2cH=CH 2;
M is selected from H, Na, K or Li;
Or,
In logical formula I compound,
R 1be selected from-OCH 3;
R 2be selected from SO 2cH=CH 2;
M is selected from H, Na, K or Li.
3. according to Yellow active dye according to claim 2, it is characterized in that: in logical formula I compound, M is selected from H or Na.
4., according to a preparation method for Yellow active dye according to claim 1, it is characterized in that:
Using the 1-(2 as coupling component, 5-bis-chloro-4-sulfonic group phenyl)-3-methyl-5-pyrazolone and diazo component be hydrolyzed the vinyl-sulfone reactive yellow dye obtained as shown in logical formula I in the basic conditions by the solution that diazotization, coupled reaction obtain, its hydrolysising reacting temperature is 20 ~ 60 DEG C, pH is between 8 ~ 12, do not saltout in preparation process, product convection drying.
5. one kind is applied in protein fibre, synthon, the dyeing of cellulosic fibre or stamp according to reactive dyestuffs according to claim 1.
CN201410543435.0A 2014-10-14 2014-10-14 Yellow active dye and preparation and application thereof Pending CN105566945A (en)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2657205A (en) * 1950-01-09 1953-10-27 Hoechst Ag Dyes containing a vinyl sulfone
DE960534C (en) * 1950-01-09 1957-03-21 Hoechst Ag Process for the production of real colors and prints
GB947607A (en) * 1961-05-03 1964-01-22 Ici Ltd Chromium-containing azomethine dyestuffs
US4934009A (en) * 1987-03-26 1990-06-19 Sumitomo Chemical Company, Limited Stabilized aqueous liquid composition of fiber-reactive azo dye: mixture with vinyl-sulphonyl and beta-sulphato ethyl-sulphonyl substituents for low temperature stability
CN1114664A (en) * 1994-02-19 1996-01-10 赫彻斯特股份公司 Active dye mixture
CN1222542A (en) * 1997-12-11 1999-07-14 西巴特殊化学品控股有限公司 Process for dyeing or printing and novel reactive dyes
CN101302355A (en) * 2007-05-08 2008-11-12 上海雅运纺织化工有限公司 Yellow reactive dye composition and use thereof
CN101376748A (en) * 2007-08-27 2009-03-04 明德国际仓储贸易(上海)有限公司 Yellow dye compound and ink composition thereof
CN103773074A (en) * 2012-10-18 2014-05-07 浙江龙盛化工研究有限公司 Yellow reactive dye compound

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2657205A (en) * 1950-01-09 1953-10-27 Hoechst Ag Dyes containing a vinyl sulfone
DE960534C (en) * 1950-01-09 1957-03-21 Hoechst Ag Process for the production of real colors and prints
GB947607A (en) * 1961-05-03 1964-01-22 Ici Ltd Chromium-containing azomethine dyestuffs
US4934009A (en) * 1987-03-26 1990-06-19 Sumitomo Chemical Company, Limited Stabilized aqueous liquid composition of fiber-reactive azo dye: mixture with vinyl-sulphonyl and beta-sulphato ethyl-sulphonyl substituents for low temperature stability
CN1114664A (en) * 1994-02-19 1996-01-10 赫彻斯特股份公司 Active dye mixture
CN1222542A (en) * 1997-12-11 1999-07-14 西巴特殊化学品控股有限公司 Process for dyeing or printing and novel reactive dyes
CN101302355A (en) * 2007-05-08 2008-11-12 上海雅运纺织化工有限公司 Yellow reactive dye composition and use thereof
CN101376748A (en) * 2007-08-27 2009-03-04 明德国际仓储贸易(上海)有限公司 Yellow dye compound and ink composition thereof
CN103773074A (en) * 2012-10-18 2014-05-07 浙江龙盛化工研究有限公司 Yellow reactive dye compound

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