CN105273440A - Red reactive dye mixture - Google Patents
Red reactive dye mixture Download PDFInfo
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- CN105273440A CN105273440A CN201410224728.2A CN201410224728A CN105273440A CN 105273440 A CN105273440 A CN 105273440A CN 201410224728 A CN201410224728 A CN 201410224728A CN 105273440 A CN105273440 A CN 105273440A
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Abstract
The invention discloses a red reactive dye mixture. The dye mixture is formed by mixing of three different dyes according to a mass ratio of 70-80:10-15:10-15. The reactive dye has the advantages of excellent sunlight fastness, perspiration fastness and rubbing fastness, and compared with all components in the composition, the performance of the mixture is higher than that of any single color variety or mixture of other ratio.
Description
Technical field
The present invention relates to a kind of red reactive dye mixture and Synthesis and applications thereof, belong to dye field.
Background technology
Recently, using reactive dyestuffs to carry out the economical efficiency of printing and dyeing to dyeing quality and dyeing process has very high requirement, and therefore need reactive dyestuffs to have good character, some facile dye composites of novel appearance with good nature are developed.The textiles used out of doors, as sportwear, and army, the BDU dress of police, often need to have good light fastness, crock fastness and perspiration fastness, and the composite behaviour of current reactive dyestuffs often can not be satisfied the demand.
Be badly in need of exploitation one group of dyestuff in the market, in particular for having the dyestuff of excellent fastness performance during printed fabrics, it can be used for dyeing to the dyestuff of hydroxyl or nitrogen-containing fiber and stamp, also can for printing hydroxyl or nitrogenous fibre materials in ink jet printing, this dyestuff should have excellent sun-resistant, perspiration resistance, the performance of rub resistance.
Because the monochromatic new product of reactive dyestuffs is in recent years little, the component much with the dye mixture of premium properties is all be selected from reactive dyestuffs known at present, then the dyestuff with good compatibleness is filtered out by analysis, these dye combinations carry out compound synergic in specific ratio, may produce beyond thought effect, namely a lot of application performance is apparently higher than the mixture of any monochromatic kind or other proportionings.
Summary of the invention
The invention provides a kind of red reactive dye mixture, it has excellent sun-resistant, perspiration resistance, the performance of rub resistance.
Red reactive dye mixture of the present invention, be particularly suited for dyeing and the stamp of fibrous material, described dye mixture by meet general formula (1), (2), (3) dyestuff mix by 70-80:15-10:15-10 mass ratio.
Wherein
R
3for
X in formula
1, X
2, X
3, X
4be independently F or Cl;
R
1, R
2be independently
Preferably, the mass ratio of the dyestuff of described general formula (1) dyestuff, general formula (2) dyestuff and general formula (3) is 75:15:10.
Preferred, preferably state dyestuff, the dyestuff of formula (2-1) and the mixture of formula (3-1) dyestuff that red reactive dye mixture is following formula (1-1):
Or the mixture of the dyestuff of formula (1-2), the dyestuff of formula (2-1) and the dyestuff of formula (3-1):
Or the mixture of the dyestuff of formula (1-3), the dyestuff of formula (2-1) and the dyestuff of formula (3-1):
Or the mixture of the dyestuff of formula (1-1), the dyestuff of formula (2-1) and the dyestuff of formula (3-2):
Or the following mixture of the dyestuff of formula (1-2), the dyestuff of formula (2-1) and the dyestuff of formula (3-2):
Or the mixture of the dyestuff of formula (1-3), the dyestuff of formula (2-1) and the dyestuff of formula (3-2):
Or the mixture of the dyestuff of formula (1-1), the dyestuff of formula (2-1) and the dyestuff of formula (3-3):
Or the mixture of the dyestuff of formula (1-2), the dyestuff of formula (2-1) and the dyestuff of formula (3-3):
Or the mixture of the dyestuff of formula (1-3), the dyestuff of formula (2-1) and the dyestuff of formula (3-3):
The present invention also comprises the preparation method of formula (1), (2), (3).
The preparation method of formula (1) orchil comprises the following steps: by formula (a) compound at PH=3.0, primary condensation is carried out with the compound of formula (b) under the condition that T < is 5 DEG C, then carry out second time condensation with the compound containing R1 at PH=4.5-6.0 and obtain secondary condensation thing, then by the compound of formula (d) 0-5 DEG C of diazotization, finally under the condition of T=5-10 DEG C, PH=6-7, the compound of formula (1) can be obtained with the coupling of secondary condensation thing.
The preparation method of formula (2) orchil comprises the following steps: the compound of formula (e) is carried out first time condensation with the compound of formula (f) under the condition of T < 5 DEG C, then carries out the compound that second time condensation can obtain formula (2) with the compound containing R2.
The preparation method of formula (3) orchil comprises the following steps: by the compound of formula g under the condition of T=5-50 DEG C, PH=3-6 and containing formula R
3compound (such as halides) carry out condensation, the compound of formula 3 can be obtained,
Formula (1), (2), (3) dyestuff mass ratio are in the mixture respectively within the scope of 70-80:15-10:15-10.If the proportioning of each component exceeds this limited range, the properties of dyestuff all can decline, and does not reach the requirement of dye mixture of the present invention.
Various dyestuff in the present invention or with the form of free acid or be preferably the form of its salt, but also can be basic metal, alkaline-earth metal and ammonium salt, and the salt of organic amine.
Red dye mixture of the present invention is suitable for dyeing and printing, and widely, such as it can be used as the dyeing of hydroxyl or nitrogenous filamentary material to its range of application, and this nitrogenous fibre materials can be that silk is thick, leather, wool, tynex and urethane; It also can be suitable for printing the containing cellulose fiber material of all kinds, and the filamentary material of these cellulose comprises native cellulose fibre, as cotton, flax and hemp, and Mierocrystalline cellulose and regenerated cellulose, such as cotton.Reactive dyestuffs of the present invention are also suitable for the dyeing of stamp cellulosic blend fabrics, the mixture of such as cotton and tynex, or particularly cotton/polyester blend fibres.
Can be in every way during dyeing, particularly with the form of aqueous dye solutions and dye printing paste reactive dyestuffs of the present invention be applied to filamentary material and be fixed on fiber, such as use aqueous dye solutions (optional saliferous) dipping articles, and with alkaline purification or in the presence of a base process after, namely dyestuff is fixed; If needed, can adopt heating or by carrying out in room temperature storage a few hours.After the fixing of dye, adopt cold water and hot water rinsing dyeing or stamp product, can add during rinsing and there is dissemination and promote the reagent that non-fixed dye spreads.
Reactive dyestuffs of the present invention have sunlight fastness, fastness to perspiration, the feature of the excellent property of fastness to rubbing, and compared to each component in its composition, its performance is higher than the mixture of any monochromatic kind or other proportionings.
Embodiment
The following example is used for illustrating the present invention, and unless otherwise, temperature is degree Celsius to provide, and part is mass parts, and per-cent is mass percent, and mass parts relates to kg/L than the parts by volume represented.
Embodiment 1,
The preparation of formula (1-1) dyestuff:
184.5 parts of cyanuric chlorides are pulled an oar 30 minutes in frozen water, under the condition of T=0 DEG C, pH=4-7, then to add 34.1 parts
add reaction 160 minutes, then by 30.9 parts
be added in T=40 DEG C, react 1 hour under the condition of pH=5-9, by 41.1 parts
under the condition of < 5 DEG C, carry out diazotization, then diazonium product and condenses are reacted 2 hours under the condition of T=5-10 DEG C, pH=6.0-8.0, the compound of formula (1-1) can be obtained.
The preparation of formula (1-2) dyestuff:
184.5 parts of cyanuric chlorides are pulled an oar 30 minutes in frozen water, under the condition of T=0 DEG C, pH=4-7, then to add 34.1 parts
add reaction 160 minutes, then by 28.1 parts
be added in T=40 DEG C, react 1 hour under the condition of pH=5-9, by 41.1 parts
under the condition of T < 5 DEG C, carry out diazotization, then by the coupling 2 hours under the condition of T=5-10 DEG C, pH=6.0-8.0 of diazonium product and condenses, the compound of formula (1-2) can be obtained.
The preparation of formula (1-3) dyestuff:
184.5 parts of cyanuric fluorides are pulled an oar 30 minutes in frozen water, under the condition of T=0 DEG C, pH=4-7, then to add 34.1 parts
add reaction 160 minutes, then by 30.9 parts
be added in T=10-20 DEG C, react 1 hour under the condition of pH=5-9, by 41.1 parts
under the condition of T < 5 DEG C, carry out diazotization, then diazonium product and condenses reacted 2 hours under the condition of T=5-10 DEG C, pH=6.0-8.0, the compound of formula (1-3) can be obtained.
Embodiment 2
The preparation of formula (2-1) dyestuff:
By 51.8 parts of formulas
compound pull an oar in frozen water 1 hour, then by 14 parts of cyanuric fluorides T < 5 DEG C, drip under the condition of pH=5-7, add reaction 30 minutes, then add the H of 25.2 parts
2nCH
2cH
2oCH
2cH
2sO
2cH
2cH
2cl carries out second time condensation reaction at T=20-40 DEG C, pH=5.0-10.0, can obtain the compound of formula 2-1.
Embodiment 3
The preparation of formula (3-1) dyestuff:
By 63.3 parts of formulas
compound pull an oar in water 1 hour, completely dissolve after, add 20.1 parts
react 120 minutes under T=40-55 DEG C, pH=5-8, the compound of formula (3-1) can be obtained.
The preparation of formula (3-2) dyestuff:
By 63.3 parts of formulas
compound pull an oar in water 1 hour, completely dissolve after, add 9.23 parts of cyanuric chlorides, first react 120 minutes under T=0-5 DEG C, pH=5-8, then at T=40-55 DEG C, react 180 minutes under pH=5-8, the compound of formula (3-2) can be obtained.
The preparation of formula (3-3) dyestuff:
By 63.3 parts of formulas
compound pull an oar in water 1 hour, completely dissolve after, add 16.8 parts
react 120 minutes under T=40-55 DEG C, pH=5-8, the compound of formula (3-3) can be obtained.
Embodiment 4 dyes
100 parts of cotton fabrics are incorporated at the temperature of 60 DEG C containing 1.5 parts of formula (1-1) dyestuffs, 0.3 part of formula (2-1) dyestuff, 0.2 part of formula (3-1) dyestuff is put in 1000 parts of water containing in the dye pond of 60 parts of sodium-chlor, at the temperature of 60 DEG C after 45 minutes, add 20 parts of soda ash, the temperature in dye pond is kept 60 DEG C, maintain 45 minutes again, then, fabric rinsing and the drying in a usual manner of dyeing, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 4, use the mixture 4a that the proportioning provided by table 1 is formed, 4b, 4c, can obtain the fabric identical with embodiment 4 performance equally.
The composition of table 1, dyestuff 4a, 4b and 4c
Embodiment 5 dyes
100 parts of cotton fabrics are incorporated at the temperature of 60 DEG C containing 1.5 parts of formula (1-2) dyestuffs, 0.3 part of formula (2-1) dyestuff, 0.2 part of formula (3-1) dyestuff is put in 1000 parts of water containing in the dye pond of 60 parts of sodium-chlor, at the temperature of 60 DEG C after 45 minutes, add 20 parts of soda ash, the temperature in dye pond is kept 60 DEG C, maintain 45 minutes again, then, fabric rinsing and the drying in a usual manner of dyeing, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 5, mixture 5a, 5b, 5c of using the proportioning provided by table 2 to be formed, can obtain the red fabric identical with embodiment 5 performance equally.
The composition of table 2, dyestuff 5a, 5b and 5c
Embodiment 6 dyes
100 parts of cotton fabrics are incorporated at the temperature of 60 DEG C containing 1.5 parts of formula (1-3) dyestuffs, 0.3 part of formula (2-1) dyestuff, 0.2 part of formula (3-1) dyestuff is put in 1000 parts of water containing in the dye pond of 60 parts of sodium-chlor, at the temperature of 60 DEG C after 45 minutes, add 20 parts of soda ash, the temperature in dye pond is kept 60 DEG C, maintain 45 minutes again, then, fabric rinsing and the drying in a usual manner of dyeing, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 6, mixture 6a, 6b, 6c of using the proportioning provided by table 3 to be formed, can obtain the red fabric identical with embodiment 6 performance equally.
The composition of table 3, dyestuff 6a, 6b and 6c
Embodiment 7 stamp
Under fast stirring by 3 parts of formula (1-1) dyestuffs, 0.6 part of formula (2-1) dyestuff, 0.4 part of formula (3-2) dyestuff puts into 100 parts containing 50 part of 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, in the stock thickener of 1 part of m-nitrobenzene sodium sulfonate, PRINTED FABRIC gas in 102 DEG C of saturation steams of the stamp paste printed cotton fabric drying gained so obtained is used to steam 2 minutes, then rinsing and drying, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 7, mixture 7a, 7b, 7c of using the proportioning provided by table 4 to be formed, can obtain the red fabric identical with embodiment 7 performance equally.
The composition of table 4, dyestuff 7a, 7b and 7c
Embodiment 8 stamp
Under fast stirring by 3 parts of formula (1-2) dyestuffs, 0.6 part of formula (2-1) dyestuff, 0.4 part of formula (3-2) dyestuff puts into 100 parts containing 50 part of 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, in the stock thickener of 1 part of m-nitrobenzene sodium sulfonate, PRINTED FABRIC gas in 102 DEG C of saturation steams of the stamp paste printed cotton fabric drying gained so obtained is used to steam 2 minutes, then rinsing and drying, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 8, mixture 8a, 8b, 8c of using the proportioning provided by table 5 to be formed, can obtain the red fabric identical with embodiment 8 performance equally.
The composition of table 5, dyestuff 8a, 8b and 8c
Embodiment 9 stamp
Under fast stirring by 3 parts of formula (1-3) dyestuffs, 0.6 part of formula (2-1) dyestuff, 0.4 part of formula (3-2) dyestuff puts into 100 parts containing 50 part of 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, in the stock thickener of 1 part of m-nitrobenzene sodium sulfonate, PRINTED FABRIC gas in 102 DEG C of saturation steams of the stamp paste printed cotton fabric drying gained so obtained is used to steam 2 minutes, then rinsing and drying, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 9, mixture 9a, 9b, 9c of using the proportioning provided by table 6 to be formed, can obtain the red fabric identical with embodiment 9 performance equally.
The composition of table 6, dyestuff 9a, 9b and 9c
Embodiment 10 stamp
Under fast stirring by 3 parts of formula (1-1) dyestuffs, 0.6 part of formula (2-1) dyestuff, 0.4 part of formula (3-3) dyestuff puts into 100 parts containing 50 part of 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, in the stock thickener of 1 part of m-nitrobenzene sodium sulfonate, PRINTED FABRIC gas in 102 DEG C of saturation steams of the stamp paste printed cotton fabric drying gained so obtained is used to steam 2 minutes, then rinsing and drying, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 10, mixture 10a, 10b, 10c of using the proportioning provided by table 7 to be formed, can obtain the red fabric identical with embodiment 10 performance equally.
The composition of table 7, dyestuff 10a, 10b and 10c
Embodiment 11 stamp
Under fast stirring by 3 parts of formula (1-2) dyestuffs, 0.6 part of formula (2-1) dyestuff, 0.4 part of formula (3-3) dyestuff puts into 100 parts containing 50 part of 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, in the stock thickener of 1 part of m-nitrobenzene sodium sulfonate, PRINTED FABRIC gas in 102 DEG C of saturation steams of the stamp paste printed cotton fabric drying gained so obtained is used to steam 2 minutes, then rinsing and drying, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 11, mixture 11a, 11b, 11c that the proportioning using according to the form below 8 to provide is formed, can obtain the red fabric identical with embodiment 11 performance equally.
The composition of table 8, dyestuff 11a, 11b and 11c
Embodiment 12 stamp
Under fast stirring by 3 parts of formula (1-3) dyestuffs, 0.6 part of formula (2-1) dyestuff, 0.4 part of formula (3-3) dyestuff puts into 100 parts containing 50 part of 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, in the stock thickener of 1 part of m-nitrobenzene sodium sulfonate, PRINTED FABRIC gas in 102 DEG C of saturation steams of the stamp paste printed cotton fabric drying gained so obtained is used to steam 2 minutes, then rinsing and drying, obtain sun-resistant, perspiration resistance, the red fabric of fastness to rubbing excellent property.
According to the method for embodiment 12, mixture 12a, 12b, 12c that the proportioning using according to the form below to provide is formed, can obtain the red fabric identical with embodiment 12 performance equally.
The composition of table 9, dyestuff 12a, 12b and 12c
Table 10 is dye mixture of the present invention but dye mixture experimental data contrast tables when apply the application ratio range beyond identical with instant component with one-component dye well:
Table 10, the dye mixture experimental data contrast table when applying
The dyestuff being numbered 1-7 is the one-component of mixture of the present invention, the dye mixture being numbered 8-16 is identical with inventive mixture component, but proportioning is different, the dyestuff being numbered 17-52 is dye mixture of the present invention, as can be seen from the above table, the properties compared with the dyestuff being numbered 1-7 being numbered the dyestuff of 8-16 is not obviously distinguished, the dyestuff of the dyestuff and numbering 1-7 that are numbered 17-52 is compared with numbering 8-16, properties all has greatly improved, special in light fastness, perspiration fastness, in dry fastness these several performances, performance obviously, the mixture (being numbered the dyestuff of 8-16) specified by the mixture (dyestuff of numbering 17-52) in the ratio range specified in the application and the present invention outside ratio range is described, and any one-component of mixture of the present invention (being numbered the dyestuff of 1-7) is compared, properties all increases significantly.
Claims (11)
1. a red reactive dye mixture, is characterized in that: described dye mixture is mixed by 70-80:10-15:10-15 mass ratio by the dyestuff of general formula (1), general formula (2) and general formula (3),
Wherein:
R
3for
X
1, X
2, X
3, X
4be independently F or Cl;
R
1, R
2be independently
2. red reactive dye mixture according to claim 1, is characterized in that: the mass ratio of the dyestuff of the dyestuff of described general formula (1), the dyestuff of general formula (2) and general formula (3) is 75:15:10.
3. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-1) dyestuff, formula (2-1) dyestuff and formula (3-1) dyestuff,
4. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-2) dyestuff, formula (2-1) dyestuff and formula (3-1) dyestuff,
5. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-3) dyestuff, formula (2-1) dyestuff and formula (3-1) dyestuff,
6. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-1) dyestuff, formula (2-1) dyestuff and formula (3-2) dyestuff,
7. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-2) dyestuff, formula (2-1) dyestuff and formula (3-2) dyestuff,
8. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-3) dyestuff, formula (2-1) dyestuff and formula (3-2) dyestuff,
9. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-1) dyestuff, formula (2-1) dyestuff and formula (3-3) dyestuff,
10. red reactive dye mixture according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-2) dyestuff, formula (2-1) dyestuff and formula (3-3) dyestuff,
11. red reactive dye mixtures according to claim 1 and 2, is characterized in that: described dye mixture is made up of formula (1-3) dyestuff, formula (2-1) dyestuff and formula (3-3) dyestuff,
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| CN201410224728.2A CN105273440B (en) | 2014-05-26 | 2014-05-26 | Red reactive dye mixture |
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|---|---|---|---|
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| CN105273440B CN105273440B (en) | 2017-02-08 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107793787A (en) * | 2016-09-06 | 2018-03-13 | 湖北丽源科技股份有限公司 | A kind of red reactive dye mixture and its application |
| CN111032790A (en) * | 2017-09-01 | 2020-04-17 | 日本化药株式会社 | Reactive dye composition and dyeing method using same |
| CN111117293A (en) * | 2019-12-23 | 2020-05-08 | 湖北丽源科技股份有限公司 | Composite reactive brilliant red dye composition and preparation method and application thereof |
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| EP0745650A1 (en) * | 1995-05-31 | 1996-12-04 | Bayer Ag | Polyfunctional azo reactive dyes |
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| CN107793787A (en) * | 2016-09-06 | 2018-03-13 | 湖北丽源科技股份有限公司 | A kind of red reactive dye mixture and its application |
| CN111032790A (en) * | 2017-09-01 | 2020-04-17 | 日本化药株式会社 | Reactive dye composition and dyeing method using same |
| CN111117293A (en) * | 2019-12-23 | 2020-05-08 | 湖北丽源科技股份有限公司 | Composite reactive brilliant red dye composition and preparation method and application thereof |
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| CN105273440B (en) | 2017-02-08 |
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