CN103351644A - High-performance multi-azo brown reactive dye, as well as synthesis and application of mixture of high-performance multi-azo brown reactive dye - Google Patents
High-performance multi-azo brown reactive dye, as well as synthesis and application of mixture of high-performance multi-azo brown reactive dye Download PDFInfo
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- CN103351644A CN103351644A CN2013102857912A CN201310285791A CN103351644A CN 103351644 A CN103351644 A CN 103351644A CN 2013102857912 A CN2013102857912 A CN 2013102857912A CN 201310285791 A CN201310285791 A CN 201310285791A CN 103351644 A CN103351644 A CN 103351644A
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- 0 *C([C@](C([C@@]1N=NI)C(O)=O)N=N*)=CC1N Chemical compound *C([C@](C([C@@]1N=NI)C(O)=O)N=N*)=CC1N 0.000 description 2
- YQTLUDKGCRNRKK-UHFFFAOYSA-N CCCC1C2C3C=CCC2C3C1 Chemical compound CCCC1C2C3C=CCC2C3C1 YQTLUDKGCRNRKK-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a high-performance multi-azo brown reactive dye which comprises a multi-azo dye shown in formula I or formula II (see the specification). The reactive dye is applicable to dip dyeing, continuous coloring and printing on cellulosic fiber including cotton, flax and mucilage glue or protein fiber including fur and silk, and the colors vary from yellow light brown to nigger-brown. The high-performance multi-azo brown reactive dye has higher color absorption rate and fixation rate, higher wet-processing fastness including bear washing and perspiration, and excellent color fastness to sunlight. As a monogenetic dyestuff, the high-performance multi-azo brown reactive dye is free from the defects of bad continuous dyeing in the head, tail and central parts.
Description
Technical field
The present invention relates to the synthetic of a kind of reactive polyazo brown dye, and a kind of application of high property polyazo brown active dye.
Background technology
Commonly using brown in the market generally all is that colorant match forms, because the difference on each component dye structure causes its substantivity to fiber to differ greatly, make the speed of dying on the fiber inconsistent, cause occurring in the especially continuous dyeing process of dyeing course the look flower, it is poor also can to cause simultaneously in the end to end poor and limit of fiber, needs that can not satisfying the market.
Involved brown dye of the present invention is the single structure dyestuff, and molecule contains a plurality of color development group, has good depth and lifting force, has simultaneously good level-dyeing property, very high dye uptake and degree of fixation, and excellent wet colour fastness.Be specially adapted to continuous gadolinium dyeing, bright in colour full, overcome the at present shortcoming of colorant match dyestuff commonly used, improved the one-time success rate of dyeing.
Present commercially available active brown dye, also there is not a gratifying brown dye on coloured light, performance, JP has been sent out a series of excellent performances, good level-dyeing property for this reason, consistency is good, degree of fixation is high, can satisfying the market and the brown dye of the monochrome of the environment-friendly type of environmental requirement, further colorant match goes out high performance black and active dye on this basis, especially the one-time success rate during continuous dyeing is high when using to make printing and dyeing enterprise, reduces the printing and dyeing cost.
In view of this, outstanding the present invention.
Summary of the invention
The object of the invention is to protect a kind of high-performance polyazo brown active dye; this dyestuff is with 3; the 5-diaminobenzoic acid is tetrazo or the trisazo-reactive dyestuffs of parent; has unique homogencous dyes structure; be used for cotton; fiber crops are waited cellulosic fibre or hair; exhaust dyeing on the protein fibres such as silk; continuous dyeing and stamp; be brown; with reactive black KN-B(C.I. reactive black 5); after mixing, the black reactive orange (reactive orange GF) of assembly commonly used can obtain aterrimus series; its characteristics are not only have higher dye uptake and degree of fixation; also have simultaneously very good washable; wet colour fastness and the light fastnesss such as sweat proof have good easy detergency and higher lifting force.Owing to being monogenetic dyestuff, when continuous dyeing without poor shortcoming in the poor and limit end to end.Simple to operate during application, save the advantages such as the energy, no color differnece.
For realizing purpose of the present invention, adopt following technical scheme:
A kind of high-performance polyazo reactive dyestuffs is characterized in that, described brown polyazo dye general formula is:
The polyazo dye structure of formula I or formula II:
In the above-mentioned general formula:
R
1Has following general formula III;
R
4, R
5Different, independently be hydrogen, methyl, methoxyl group, sulfonic group separately;
R
2, R
3Can with R
1Identical, also can have following general formula IV or general formula V;
Sulfonic group is on 2,3,4 in the formula, and ethyl sulfonyl sulfate is on 3,4;
R
1, R
2, R
3The position can exchange passable;
The structure that must have a general formula III in formula I, the II at least;
Described R
1Have following formula III-1, III-2 structure:
R
3Be hydrogen, methoxyl group, sulfonic group; R
4Be hydrogen, methyl;
R
2, R
3With R
1Have identical structure, or following compound:
Sulphanilic Acid, ORTHO AMINO PHENOL SULPHONIC, m-sulfanilic acid, 4-(β-ethyl sulfonyl sulfate) aniline (para-ester), 3-(β-ethyl sulfonyl sulfate) aniline (a position ester), sulfonation para-ester, position ester between sulfonation, 2-methoxyl group-4-(β-ethyl sulfonyl sulfate) aniline (O-methoxy para-ester), 2-methoxyl group-3-(β-ethyl sulfonyl sulfate) aniline (position ester between O-methoxy), 2-methoxyl group-5-methyl-4-(β-ethyl sulfonyl sulfate) aniline (gram Li Xiding para-ester), 2-methoxyl group-5-methyl-3-(β-ethyl sulfonyl sulfate) aniline (position ester between gram Li Xiding), 2,5-dimethoxy-4 '-(β-ethyl sulfonyl sulfate) aniline (2,5-dimethoxy para-ester), 2,5-dimethoxy-3-(β-ethyl sulfonyl sulfate) aniline (between 2,5-dimethoxy position ester) etc.;
Described reactive polyazo dyes can with reactive black KN-B(C.I. reactive black 5), the commonly used black reactive orange of assembly mixes and is combined into the black use, the blending weight ratio of reactive black KN-B, reactive orange GF and formula I or formula II dyestuff is 60:5:35～75:10:15.
Described reactive polyazo dyes carries out the application of exhaust dyeing, continuous dyeing and stamp at the cellulose materials that contains hydroxyl or amino.
Another object of the present invention is to provide a kind of preparation method of above-mentioned dyestuff, for realizing the second purpose of the present invention, adopt following technical scheme:
The preparation method of above-mentioned reactive polyazo dyes, various compounds with the diazo coupling method composite structure (III) of routine, and then with (III) formula compound method diazotization with routine in sulfuric acid or hydrochloric acid, with 3, the 5-diaminobenzoic acid o'clock carries out acid coupling in pH1～2, with the method for routine with aniline sulfonic acid (neighbour, between, right) or the right 2 described compound diazotization that contain ethyl sulfonyl sulfate (active group), carry out secondary or three couplings in pH5～6 with above-mentioned acid coupling thing again, also can be first with aniline sulfonic acid (neighbour, between, right) or the right 2 described compound diazotization 3 that contain ethyl sulfonyl sulfate (active group), the 5-diaminobenzoic acid o'clock carries out acid coupling in pH1～2, carries out the brown active dye (being formula I or formula II dyestuff) that alkaline coupling obtains secondary or three couplings in pH5～6 with diazotizing (III) formula compound again.
The present invention also claimed above-mentioned reactive printing dyes carries out the application of exhaust dyeing, continuous dyeing and stamp at the cellulose materials that contains hydroxyl or amino.
Below the present invention is further detailed:
Brown dye commonly used mainly contains blue dyestuff, orchil, orange dye blending and forms in the market.But because the structural difference of yellow dyes, orange dye and blue dyes causes its substantivity to fiber to differ greatly; make the speed of dying on the fiber inconsistent; cause occurring in the especially continuous dyeing process of dyeing course the look flower; it is poor also can to cause simultaneously in the end to end poor and limit of fiber; make the one-time success rate of printing and dyeing enterprise very low; also need to repair look when serious, this cost that will cause printing and dyeing increases considerably, and can't satisfy the needs of requirement and the environment protection of enterprise.
Involved new brown dye of the present invention is the single structure dyestuff, can improve to a great extent the above-mentioned shortcoming of dyestuff, it is characterized in that using supermolecular theory and organic synthesis theoretical, with the emission system of dyestuff prolong the color red shift that makes dyestuff (wavelength increases, color increase deeply), to the substantivity increase of fiber, thereby make this class dyestuff have good depth and lifting force, have simultaneously good level-dyeing property, very high dye uptake and degree of fixation, and excellent wet colour fastness.Be specially adapted to continuous gadolinium dyeing, bright in colour full, overcome the at present shortcoming of colorant match dyestuff commonly used, improved the one-time success rate of dyeing, satisfy the requirement of enterprise.
A kind of high-performance polyazo reactive dyestuffs is characterized in that, described brown polyazo dye general formula is:
The polyazo dye structure of formula I or formula II:
In the above-mentioned general formula:
R
1Has following general formula III;
R
4, R
5Different, independently be hydrogen, methyl, methoxyl group, sulfonic group separately;
R
2, R
3Can with R
1Identical, also can have following general formula IV or general formula V;
Sulfonic group is on 2,3,4 in the formula, and ethyl sulfonyl sulfate is on 3,4;
R
1, R
2, R
3The position can exchange passable;
The structure that must have a general formula III in formula I, the II at least;
Described R
1Have following formula III-1, III-2 structure:
R
4Be hydrogen, methoxyl group, sulfonic group; R
5Be hydrogen, methyl;
R
2, R
3With R
1Have identical structure, or following compound:
Sulphanilic Acid, ORTHO AMINO PHENOL SULPHONIC, m-sulfanilic acid, 4-(β-ethyl sulfonyl sulfate) aniline (para-ester), 3-(β-ethyl sulfonyl sulfate) aniline (a position ester), sulfonation para-ester, position ester between sulfonation, 2-methoxyl group-4-(β-ethyl sulfonyl sulfate) aniline (O-methoxy para-ester), 2-methoxyl group-3-(β-ethyl sulfonyl sulfate) aniline (position ester between O-methoxy), 2-methoxyl group-5-methyl-4-(β-ethyl sulfonyl sulfate) aniline (gram Li Xiding para-ester), 2-methoxyl group-5-methyl-3-(β-ethyl sulfonyl sulfate) aniline (position ester between gram Li Xiding), 2,5-dimethoxy-4 '-(β-ethyl sulfonyl sulfate) aniline (2,5-dimethoxy para-ester), 2,5-dimethoxy-3-(β-ethyl sulfonyl sulfate) aniline (between 2,5-dimethoxy position ester) etc.;
As preferred implementation of the present invention, the brown dye structure of preferred formula I is as shown in the formula (I-1～I-12):
As preferred implementation of the present invention, the brown dye structure of preferred formula II is as shown in the formula (II-1～II-8):
The polyazo dye of formula I can get with common diazonium coupling method, be about to general formula III and amino phenyl sulfonyl acid compound, to () a position ester series compound carries out respectively diazotization with Sodium Nitrite in sulfuric acid or hydrochloric acid, then with 3, the 5-diaminobenzoic acid carries out respectively acidity, alkaline coupling, forms tris-azo compound.
The polyazo dye of general formula II can get with common diazonium coupling method, be about to general formula III and amino phenyl sulfonyl acid compound, to () a position ester series compound carries out respectively diazotization with Sodium Nitrite in sulfuric acid or hydrochloric acid, then with 3, the 5-diaminobenzoic acid carries out respectively acidity, alkaline coupling, forms two azo-compounds.
The monoazo-dyes of general formula III also is to get with common diazonium coupling method, and the compound that is about to para-ester series carries out diazotization with Sodium Nitrite in hydrochloric acid, then carry out coupling with 2-amino-4-kharophen Phenylsulfonic acid.
Described reactive polyazo dyes can with reactive black KN-B(C.I. reactive black 5), the commonly used black reactive orange of assembly mixes and is combined into the black use, the blending weight ratio of reactive black KN-B, reactive orange GF and formula I or formula II dyestuff is 60:5:35～75:10:15.
Described reactive polyazo dyes carries out the application of exhaust dyeing, continuous dyeing and stamp at the cellulose materials that contains hydroxyl or amino.
Reactive polyazo dyes of the present invention and composition thereof is for the application of carrying out exhaust dyeing, continuous dyeing and stamp on the cellulosic fibre.Continuous dyeing, form the gadolinium dye liquor with an amount of dyestuff, adding levelling agent etc., again caustic soda, soda ash, salt are made into fixation liquid, through soaking the gadolinium dye liquor, drying, soak the techniques such as gadolinium fixation liquid, decatize, washing, drying, can obtain the product of excellent property, not only have higher dye uptake and degree of fixation, also have simultaneously wet colour fastness and the light fastnesss such as very good washable, sweat proof, have good easy detergency and higher lifting force.Without poor shortcoming in the poor and limit end to end.Simple to operate during application, the saving energy.
Following example is used for explanation content of the present invention, and except as otherwise noted, temperature be degree centigrade, part and per-cent be weight part and weight percent, the relation of weight part and parts by volume with kilogram and the relationship consistency of liter.
Embodiment
The preparation of embodiment 1 polyazo brown dye I-1
In 1000 milliliters beaker, add 200 parts of water, 52.3 parts of formula III-1 compound (R
4, R
5Be hydrogen), 0.1 part of dispersion agent, stirring to pulp 1h, the hydrochloric acid that adds 35 part 30% carried out diazotization reaction 2 hours at 0～5 ℃ of lower sodium nitrite solution that adds 23 part 30%, added the excessive nitrous acid of thionamic acid destruction behind terminal point, then join in 15.2 part 15% the 3.5-diaminobenzoic acid solution, be warming up to 10～15 ℃, the sodium acetate soln with 15% is regulated pH=1～2, reacts 4～6 hours, be terminal point during without diazonium salt, for subsequent use.
In 1000 milliliters beaker, add 300 parts of water, 56.2 parts of formula para-esters, 0.1 part of dispersion agent, stirring to pulp 1h, the hydrochloric acid that adds 60 part 30%, carried out diazotization reaction 2 hours at 0～5 ℃ of lower sodium nitrite solution that adds 46 part 30%, behind terminal point, add the excessive nitrous acid of thionamic acid destruction, join in the above-mentioned acid coupling thing, sodium carbonate solution with 20% is regulated about pH=4 and is carried out coupling 2h, again pH is transferred to 5～6 and carries out alkaline coupling 2～3h, be terminal point during without diazonium salt, convection drying obtains dyestuff I-1.
The embodiment 2-24 polyazo brown dye I-preparation of 2～I-12 and preparation of other structures
Method with reference to embodiment 1 changes different R
1, R
2, R
3Diazo component can obtain dyestuff I-2～I-12 and other polyazo brown dye.
Only exemplified the part dyestuff of formula I herein, those skilled in the art will envision that and adopt dyestuff I that different reactants can obtain having different substituents with final realization the present invention, length is limit herein, repeats no more.
The preparation of embodiment 25 polyazo brown dye II-1
In 1000 milliliters beaker, add 200 parts of water, 52.3 parts of formula III-1 compound (R
4, R
5Be hydrogen), 0.1 part of dispersion agent, stirring to pulp 1h, the hydrochloric acid that adds 35 part 30% carried out diazotization reaction 2 hours at 0～5 ℃ of lower sodium nitrite solution that adds 23 part 30%, added the excessive nitrous acid of thionamic acid destruction behind terminal point, then join in 15.2 part 15% the 3.5-diaminobenzoic acid solution, be warming up to 10～15 ℃, the sodium acetate soln with 15% is regulated pH=1～2, reacts 4～6 hours, be terminal point during without diazonium salt, for subsequent use.
In 1000 milliliters beaker, add 150 parts of water, 28.1 parts of formula para-esters, 0.1 part of dispersion agent, stirring to pulp 1h adds 30 part 30% hydrochloric acid, carries out diazotization reaction 2 hours at 0～5 ℃ of lower sodium nitrite solution that adds 23 part 30%, behind terminal point, add the excessive nitrous acid of thionamic acid destruction, join in the above-mentioned acid coupling thing, the sodium carbonate solution with 20% is regulated pH4～5 and is carried out alkaline coupling 2～3h, is terminal point during without diazonium salt, convection drying obtains dyestuff II-1.
The embodiment 26-24 polyazo brown dye II-preparation of 2～II-8 and preparation of other structures
Method with reference to embodiment 25 changes different R
1, R
2Diazo component can obtain dyestuff II-2～II-8 and other polyazo brown dye.
Only exemplified the part dyestuff of general formula II herein, those skilled in the art will envision that and adopt dyestuff II that different reactants can obtain having different substituents with final realization the present invention, length is limit herein, repeats no more.
Embodiment 49 active pitch black preparations
Get 70 parts of reactive black KN-B, 25 parts of examples, 1 synthetic formula I-1 dyestuff and 5 parts of reactive orange GF dyestuffs mix, adding suitable auxiliary agent carries out commercialization and obtains commercial dye, get 5 parts of addings of this mixture 2 parts of wetting agent B, 13 parts of dyeing accelerant PT and be made into dye liquor, again 6 parts of caustic soda, 20 portions of soda ash, 250 salt are made into fixation liquid.Carry out continuous dyeing with pure cotton fabric: soak the gadolinium dye liquor, dry, soak gadolinium fixation liquid, decatize, washing, oven dry, obtain the aterrimus fabric.
Embodiment 50 active pitch black preparations
Get 65 parts of reactive black KN-B, 30 parts of examples, 1 synthetic formula I-1 dyestuff and 5 parts of reactive orange GF dyestuffs mix, adding suitable auxiliary agent carries out commercialization and obtains commercial dye, get 5 parts of addings of this mixture 2 parts of wetting agent B, 13 parts of dyeing accelerant PT and be made into dye liquor, again 6 parts of caustic soda, 20 portions of soda ash, 250 salt are made into fixation liquid.Carry out continuous dyeing with pure cotton fabric: soak the gadolinium dye liquor, dry, soak gadolinium fixation liquid, decatize, washing, oven dry, obtain the aterrimus fabric.
The application of the brown look dyestuff of embodiment 51 high-performance polyazos I
Get 5 parts of above-mentioned dyestuff I-1, add 2 parts of wetting agent B, 13 parts of dyeing accelerant PT and be made into dye liquor, again 6 parts of caustic soda, 20 portions of soda ash, 250 salt are made into fixation liquid.Carry out continuous dyeing with pure cotton fabric: soak the gadolinium dye liquor, dry, soak gadolinium fixation liquid, decatize, washing, oven dry, obtain brown yarn dyed fabric.
The application of the brown look dyestuff of embodiment 52 high-performance polyazos II
Get 5 parts of above-mentioned dyestuff II-1, add 2 parts of wetting agent B, 13 parts of dyeing accelerant PT and be made into dye liquor, again 6 parts of caustic soda, 20 portions of soda ash, 250 salt are made into fixation liquid.Carry out continuous dyeing with pure cotton fabric: soak the gadolinium dye liquor, dry, soak gadolinium fixation liquid, decatize, washing, oven dry, obtain brown yarn dyed fabric.
The application of embodiment 53 high-performance polyazo black dyess
Get the aterrimus dyestuff of 5 parts of examples 49, add 2 parts of wetting agent B, 13 parts of dyeing accelerant PT and be made into dye liquor, again 6 parts of caustic soda, 20 portions of soda ash, 250 salt are made into fixation liquid.Carry out continuous dyeing with pure cotton fabric: soak the gadolinium dye liquor, dry, soak gadolinium fixation liquid, decatize, washing, oven dry, obtain the aterrimus fabric.
The application of embodiment 54 high-performance polyazo black dyess
Get the aterrimus dyestuff of 5 parts of examples 50, add 2 parts of wetting agent B, 13 parts of dyeing accelerant PT and be made into dye liquor, again 6 parts of caustic soda, 20 portions of soda ash, 250 salt are made into fixation liquid.Carry out continuous dyeing with pure cotton fabric: soak the gadolinium dye liquor, dry, soak gadolinium fixation liquid, decatize, washing, oven dry, obtain the aterrimus fabric.
Claims (4)
1. high-performance polyazo reactive dyestuffs is characterized in that, described brown polyazo dye general formula is:
The polyazo dye structure of formula I or formula II:
In the above-mentioned general formula:
R
1Has following general formula III;
R
4, R
5Different, independently be hydrogen, methyl, methoxyl group, sulfonic group separately;
R
2, R
3Can with R
1Identical, also can have following general formula IV or general formula V;
Sulfonic group is on 2,3,4 in the formula, and ethyl sulfonyl sulfate is on 3,4;
R
1, R
2, R
3The position can exchange passable;
The structure that must have a general formula III in formula I, the II at least.
2. reactive polyazo dyes according to claim 1 is characterized in that: described R
1Have following formula III-1, III-2 structure:
R
3Be hydrogen, methoxyl group, sulfonic group; R
4Be hydrogen, methyl;
R
2, R
3With R
1Have identical structure, or following compound:
Sulphanilic Acid, ORTHO AMINO PHENOL SULPHONIC, m-sulfanilic acid, 4-(β-ethyl sulfonyl sulfate) aniline (para-ester), 3-(β-ethyl sulfonyl sulfate) aniline (a position ester), sulfonation para-ester, position ester between sulfonation, 2-methoxyl group-4-(β-ethyl sulfonyl sulfate) aniline (O-methoxy para-ester), 2-methoxyl group-3-(β-ethyl sulfonyl sulfate) aniline (position ester between O-methoxy), 2-methoxyl group-5-methyl-4-(β-ethyl sulfonyl sulfate) aniline (gram Li Xiding para-ester), 2-methoxyl group-5-methyl-3-(β-ethyl sulfonyl sulfate) aniline (position ester between gram Li Xiding), 2,5-dimethoxy-4 '-(β-ethyl sulfonyl sulfate) aniline (2,5-dimethoxy para-ester), 2,5-dimethoxy-3-(β-ethyl sulfonyl sulfate) aniline (between 2,5-dimethoxy position ester) etc.
3. reactive polyazo dyes according to claim 2, it is characterized in that: described reactive polyazo dyes can with reactive black KN-B(C.I. reactive black 5), the commonly used black reactive orange of assembly mixes and is combined into the black use, the blending weight ratio of reactive black KN-B, reactive orange and formula I or formula II dyestuff is 60:5:35～75:10:15.
4. the described reactive polyazo dyes of claim 1-4 carries out the application of exhaust dyeing, continuous dyeing and stamp at the cellulose materials that contains hydroxyl or amino.
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Cited By (6)
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|---|---|---|---|---|
| CN105694530A (en) * | 2016-03-17 | 2016-06-22 | 浙江瑞华化工有限公司 | Orange reactive dye compound, orange reactive dye composition and preparation method and application thereof |
| CN108530945A (en) * | 2018-05-18 | 2018-09-14 | 无锡润新染料有限公司 | More coupling Yellow active dyes and its built brown active dye |
| CN108530946A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of black reactive dye mixture and its application |
| CN108530942A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of brown active dye preparation method and purposes |
| CN108530943A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of black reactive dye mixture and its application |
| WO2019020122A1 (en) * | 2017-07-28 | 2019-01-31 | 浙江科永化工有限公司 | Active dark blue to black dye composition and dye product |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105694530A (en) * | 2016-03-17 | 2016-06-22 | 浙江瑞华化工有限公司 | Orange reactive dye compound, orange reactive dye composition and preparation method and application thereof |
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| CN108530942A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of brown active dye preparation method and purposes |
| CN108530943A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of black reactive dye mixture and its application |
| WO2019020122A1 (en) * | 2017-07-28 | 2019-01-31 | 浙江科永化工有限公司 | Active dark blue to black dye composition and dye product |
| US10954392B2 (en) | 2017-07-28 | 2021-03-23 | Zhejiang Keyong Chemical Co., Ltd. | Reactive navy to black dye composition and dye product thereof |
| CN108530945A (en) * | 2018-05-18 | 2018-09-14 | 无锡润新染料有限公司 | More coupling Yellow active dyes and its built brown active dye |
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Application publication date: 20131016 |