CN109825110A - A kind of weaving active cationic dye and preparation method thereof and tint applications - Google Patents
A kind of weaving active cationic dye and preparation method thereof and tint applications Download PDFInfo
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- CN109825110A CN109825110A CN201910249350.4A CN201910249350A CN109825110A CN 109825110 A CN109825110 A CN 109825110A CN 201910249350 A CN201910249350 A CN 201910249350A CN 109825110 A CN109825110 A CN 109825110A
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Abstract
The invention discloses a kind of weaving active cationic dye and preparation method thereof and tint applications.The dyestuff is that have following general formulaCompound and its derivative, wherein R1And R2It is any in H, Cl, Br or CN.To N-ethylaniline hydroxyethylation, chlorination, amination, coupling component A is obtained；Again by after 4- nitroaniline and its derivative diazotising, after coupling component A coupling reaction, then through quaternized processing to get the compound and its derivative of logical formula (I).Dyestuff provided by the invention has cation water-soluble group and epoxy-reactive group, and color presentation is orange to red coloured light, upper under salt-free conditions can contaminate cellulose fibre, reduce environmental pollution, easy to use, low in cost, application performance is excellent.
Description
Technical field
The present invention relates to Textile Dyes fields, and in particular to a kind of weaving active cationic dye and preparation method thereof
With tint applications.
Background technique
Mainly there are two steps for traditional reactive dyestuffs in exhaustion technique: firstly, reactive dye are inhaled under the rush dye effect of salt
It is attached on fiber, then, dyestuff and fiber form Covalent bonding together in the presence of alkali.Fiber from dye liquor dye extraction and to
Fibrous inside diffusion.Because the traditional activated dyestuff of cellulose fiber peacekeeping is all negatively charged in aqueous solution, needed in dyeing course
The negative electrical charge that a large amount of salt (sodium chloride or sodium sulphate) inhibits fiber surface is consumed, dye-uptake is improved.According to dye structure, face
Color is different, and salt dosage is generally 30~150g/L.The inorganic salts for being largely added or generating in Dyeing with Reactive Dyes, chloride ion
Ten thousand ppm more than 10 cannot be pocessed by simple physical chemistry and biochemical method.The discharge of high salinity waste water
It will be directly changed the water quality of rivers and lakes river water, destroys the ecological environment of water；Secondly the high osmosis of salinity will lead to rivers and lakes and printing and dyeing
The soil property salinization of soil on factory periphery, reduces the yield of crops.The salt-free dyeing of reactive dye is one of research emphasis.
CN102978952B discloses a kind of ecological low-salt dyeing and finishing agent for reactive dyes, it includes that cross-linking type cation changes
Property agent A and branched chain type cation modifier B, cross-linking type cation modifier A and the weight ratio of branched chain type cation modifier B are
(30~50): 50.Advantages of the present invention: using cross-linking type cation modifier and branched chain type cation modifier to cotton fiber into
When row processing, cation modifying can be carried out to fibrous inside and fiber surface, so as to improve the utilization rate of reactive dye, cotton
The dye-uptake and degree of fixation of fabric are obviously higher than normal dyeing；And salt-free low alkali dyeing may be implemented in dyeing course even
It is salt-free non-alkali dyeing, secondary use can be recycled in dyeing waste-water；Its washing color fastness, colour fastness to rubbing and conventional cotton fabric
It is consistent.Although the patent realizes salt-free dyeing, but carry out chemical modification to cotton fiber in advance, then dyed, process
It is cumbersome, it can not achieve step dyeing, it is therefore desirable to improve and optimizate.
Summary of the invention
In view of the deficiencies of the prior art, the purpose of the present invention is to provide a kind of weaving active cationic dye and its systems
Preparation Method and tint applications, the reactive dye upper under salt-free conditions can contaminate cellulose fibre, reduce environmental pollution, user
Just, low in cost, application performance is excellent.
A kind of weaving active cationic dye, has following general formula
Compound and its derivative, wherein R1With
R2It is any in H, Cl, Br or CN.
It is as improved, above-mentioned weaving has the following structure formula with active cationic dye
Compound.
The preparation method of above-mentioned weaving active cationic dye, comprising the following steps: step 1, to N-ethylaniline hydroxyl
Ethylization, chlorination, amination obtain coupling component A；Step 2, by after 4- nitroaniline and its derivative diazotising, with coupling component A
After coupling reaction, then through quaternized processing to get the compound and its derivative of logical formula (I).
Reaction route is as follows:
The tint applications of above-mentioned weaving active cationic dye, comprising the following steps: according to bath raio 1:30-50, dyestuff
Dosage is the 0.5-4% to fabric weight, and room temperature enters dye, and 1-2 DEG C/min is warming up to 60-70 DEG C, adds sodium carbonate 15-25g/L,
Continue to dye 40-60min, dye finishes, and washing is soaped, and washes, dyeing is completed in drying.
It is that the color of the active cationic dye is from orange to red as improved.
The utility model has the advantages that
Present invention reactive dye produced can be with band in water because its dye matrix is positively charged in aqueous solution
By contaminating on charge attraction, the rush without salt contaminates the cotton fiber of negative electrical charge.Because containing epoxy reaction base, the reactive group in dyestuff
Under the action of alkaline agent, it can react to form covalent bond with the hydroxyl on cellulose fibre.Compared to traditional activated dyestuff, the dyestuff
Salt-free dyeing can be achieved, be a kind of environmental protection type dye of suitable clean manufacturing.
Specific embodiment
Structure, the preparation method and application of dyestuff of the present invention are illustrated above, it below will be by embodiment to this
Invention work further instruction.
Embodiment 1
In pressure-resistant ethoxyl etherification pot, 58.7KgN- methylaniline is added, is heated to 130 DEG C, is passed through nitrogen expeling
Air.It is 150-152 DEG C in temperature, pressure is 3 × 105Pa is hereinafter, being passed through 26.7Kg ethylene oxide in batches (is every time 5-
8Kg).After adding, in 150-152 DEG C of heat preservation 3h, N- methyl-N- hydroxyethylaniline 75-77Kg can be obtained.
181.5Kg phosphorus oxychloride is added in chlorination reaction pot, controls temperature in 70-80 DEG C of dropwise addition N- ethyl-N- hydroxyl second
Base aniline 75.5Kg.After adding, in 90-95 DEG C of stirring 1h, N- ethyl-N- (β-chloroethyl) aniline filter cake is obtained.
In aminating reaction pot, dimethylformamide makees solvent, molar ratio N- ethyl-N- (β-chloroethyl) amino:
Dimethylamine: triethylamine is general=1:3:2,50 DEG C of reaction 2h, obtain N- ethyl-N- (N, N- dimethyl-ethylamine base) aniline.
By 284KgN- ethyl-N- (N, N- dimethyl-ethylamine base) aniline add to by 17% hydrochloric acid of 366L, 1800L water and
In the material of 3000Kg ice composition, diazo liquid is added at 5-10 DEG C and carries out coupling reaction, reaction time 4h is used after completion of the reaction
Water dilute filtration.With alkali cleaning, it is washed to neutrality, obtains dyestuff intermediate product.
Epoxychloropropane side border ring is added drop-wise in the acetone soln of previous step dyestuff intermediate product, material molar ratio 1:
1,80 DEG C is stirred to react 2 hours, evaporates acetone, isopropanol is poured into reaction solution, and precipitating is filtered, acetone cleaning, and 60 DEG C
Lower vacuum drying, obtains compound.
Using the compound of the present embodiment to the colouring method of cotton fabric:
Bath raio 1:30, dye dosage are that 1% is weighed to fabric, and room temperature enters dye, and 1 DEG C/min is warming up to 60 DEG C, and sodium carbonate is added
20g/L continues to dye 60min, and dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 7 grades of light fastness.
Embodiment 2
In pressure-resistant ethoxyl etherification pot, 58.7KgN- methylaniline is added, is heated to 130 DEG C, is passed through nitrogen expeling
Air.It is 150-152 DEG C in temperature, pressure is 3 × 105Pa is hereinafter, being passed through 26.7Kg ethylene oxide in batches (is every time 5-
8Kg).After adding, in 150-152 DEG C of heat preservation 3h, N- methyl-N- hydroxyethylaniline 75-77Kg can be obtained.
181.5Kg phosphorus oxychloride is added in chlorination reaction pot, controls temperature in 70-80 DEG C of dropwise addition N- ethyl-N- hydroxyl second
Base aniline 75.5Kg.After adding, in 90-95 DEG C of stirring 1h, N- ethyl-N- (β-chloroethyl) aniline filter cake is obtained.
In aminating reaction pot, dimethylformamide makees solvent, molar ratio N- ethyl-N- (β-chloroethyl) amino:
Dimethylamine: triethylamine is general=1:3:2,50 DEG C of reaction 2h, obtain N- ethyl-N- (N, N- dimethyl-ethylamine base) aniline.
By 284Kg N- ethyl-N- (N, N- dimethyl-ethylamine base) aniline add to by 17% hydrochloric acid of 366L, 1800L water and
In the material of 3000Kg ice composition, diazo liquid is added at 5-10 DEG C and carries out coupling reaction, reaction time 4h is used after completion of the reaction
Water dilute filtration.With alkali cleaning, it is washed to neutrality, obtains dyestuff intermediate product.
Epoxychloropropane side border ring is added drop-wise in the acetone soln of previous step dyestuff intermediate product, material molar ratio 1:
1,80 DEG C is stirred to react 2 hours, evaporates acetone, isopropanol is poured into reaction solution, and precipitating is filtered, acetone cleaning, and 60 DEG C
Lower vacuum drying, obtains compound
Compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:30, dye dosage are that 1% is weighed to fabric, and room temperature enters dye, and 1 DEG C/min is warming up to 60 DEG C, and sodium carbonate is added
20g/L continues to dye 60min, and dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 7 grades of light fastness
Embodiment 3
In pressure-resistant ethoxyl etherification pot, 58.7KgN- methylaniline is added, is heated to 130 DEG C, is passed through nitrogen expeling
Air.It is 150-152 DEG C in temperature, pressure is 3 × 105Pa is hereinafter, being passed through 26.7Kg ethylene oxide in batches (is every time 5-
8Kg).After adding, in 150-152 DEG C of heat preservation 3h, N- methyl-N- hydroxyethylaniline 75-77Kg can be obtained.
181.5Kg phosphorus oxychloride is added in chlorination reaction pot, controls temperature in 70-80 DEG C of dropwise addition N- ethyl-N- hydroxyl second
Base aniline 75.5Kg.After adding, in 90-95 DEG C of stirring 1h, N- ethyl-N- (β-chloroethyl) aniline filter cake is obtained.
In aminating reaction pot, dimethylformamide makees solvent, molar ratio N- ethyl-N- (β-chloroethyl) amino:
Dimethylamine: triethylamine is general=1:3:2,50 DEG C of reaction 2h, obtain N- ethyl-N- (N, N- dimethyl-ethylamine base) aniline.
By 284KgN- ethyl-N- (N, N- dimethyl-ethylamine base) aniline add to by 366L17% hydrochloric acid, 1800L water and
In the material of 3000Kg ice composition, diazo liquid is added at 5-10 DEG C and carries out coupling reaction, reaction time 4h is used after completion of the reaction
Water dilute filtration.With alkali cleaning, it is washed to neutrality, obtains dyestuff intermediate product.
Epoxychloropropane side border ring is added drop-wise in the acetone soln of previous step dyestuff intermediate product, material molar ratio 1:
1,80 DEG C is stirred to react 2 hours, evaporates acetone, isopropanol is poured into reaction solution, and precipitating is filtered, acetone cleaning, and 60 DEG C
Lower vacuum drying obtains compound (I).
Formula (I) compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:30, dye dosage are that 1% is weighed to fabric, and room temperature enters dye, and 1 DEG C/min is warming up to 60 DEG C, and sodium carbonate is added
20g/L continues to dye 60min, and dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 7 grades of light fastness.
Embodiment 4
In pressure-resistant ethoxyl etherification pot, 58.7KgN- methylaniline is added, is heated to 130 DEG C, is passed through nitrogen expeling
Air.It is 150-152 DEG C in temperature, pressure is 3 × 105Pa is hereinafter, being passed through 26.7Kg ethylene oxide in batches (is every time 5-
8Kg).After adding, in 150-152 DEG C of heat preservation 3h, N- methyl-N- hydroxyethylaniline 75-77Kg can be obtained.
181.5Kg phosphorus oxychloride is added in chlorination reaction pot, controls temperature in 70-80 DEG C of dropwise addition N- ethyl-N- hydroxyl second
Base aniline 75.5Kg.After adding, in 90-95 DEG C of stirring 1h, N- ethyl-N- (β-chloroethyl) aniline filter cake is obtained.
In aminating reaction pot, dimethylformamide makees solvent, molar ratio N- ethyl-N- (β-chloroethyl) amino:
Dimethylamine: triethylamine is general=1:3:2,50 DEG C of reaction 2h, obtain N- ethyl-N- (N, N- dimethyl-ethylamine base) aniline.
By 284KgN- ethyl-N- (N, N- dimethyl-ethylamine base) aniline add to by 366L17% hydrochloric acid, 1800L water and
In the material of 3000Kg ice composition, diazo liquid is added at 5-10 DEG C and carries out coupling reaction, reaction time 4h is used after completion of the reaction
Water dilute filtration.With alkali cleaning, it is washed to neutrality, obtains dyestuff intermediate product.
Epoxychloropropane side border ring is added drop-wise in the acetone soln of previous step dyestuff intermediate product, material molar ratio 1:
1,80 DEG C is stirred to react 2 hours, evaporates acetone, isopropanol is poured into reaction solution, and precipitating is filtered, acetone cleaning, and 60 DEG C
Lower vacuum drying obtains compound (I).
Formula (I) compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:30, dye dosage are that 1% is weighed to fabric, and room temperature enters dye, and 1 DEG C/min is warming up to 60 DEG C, and sodium carbonate is added
20g/L continues to dye 60min, and dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 7 grades of light fastness.
Embodiment 5
Compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:30, dye dosage prepared by embodiment 1 are that 1% is weighed to fabric, and room temperature enters dye, with the heating of 1 DEG C/min
Rate is warming up to 60 DEG C, and sodium carbonate 20g/L is added, and continues to dye 40min, and dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 7 grades of light fastness.
Embodiment 6
Compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:40, dye dosage prepared by embodiment 1 are that 2% is weighed to fabric, and room temperature enters dye, is warming up to 2 DEG C/min
70 DEG C, sodium carbonate 20g/L is added, continues to dye 50min, dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 6-7 grades of light fastness.
Embodiment 7
Compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:50, dye dosage prepared by embodiment 2 are that 0.5% is weighed to fabric, and room temperature enters dye, 1.5 DEG C/min heating
To 65 DEG C, sodium carbonate 15g/L is added, continues to dye 60min, dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 7 grades of light fastness.
Embodiment 8
Compound is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:35, dye dosage prepared by embodiment 3 are that 4% is weighed to fabric, and room temperature enters dye, and 1 DEG C/min is warming up to 60
DEG C, sodium carbonate 25g/L is added, continues to dye 55min, dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 6-7 grades of light fastness.
Comparative example 1
Active dye activity Huang K-RN is present embodiments provided to the colouring method of cotton fabric:
Bath raio 1:30, active yellow K-RN dosage are that 1% is weighed to fabric, and sodium chloride 20g/L is added, and room temperature enters to contaminate, 2 DEG C/min
70 DEG C are warming up to, sodium carbonate 20g/L is added, continues to dye 60min, dye finishes, and washing is soaped, and washes, drying.
5 grades of dyeing product washing fastness, 4 grades of dry fastness, 3-4 grades of fastness to wet rubbing, 6-7 grades of light fastness.
Example 5-8 can be seen that present invention reactive dye produced compared with comparative example 1, because its dye matrix is in water
It is positively charged in solution, can be with negatively charged cotton fiber in water by being contaminated on charge attraction, the rush without salt contaminates.Because of dye
Contain epoxy reaction base in material, which can react to be formed with the hydroxyl on cellulose fibre under the action of alkaline agent
Covalent bond, wet colour fastness are high.Compared to traditional activated dyestuff, which can realize salt-free dyeing, and dyeing quality index with it is general
Logical reactive dye are suitable, are a kind of environmental protection type dyes of suitable clean manufacturing.
Above-described specific embodiment has carried out further the purpose of the present invention, technical scheme and beneficial effects
It is described in detail, it should be understood that being not limited to this hair the foregoing is merely a specific embodiment of the invention
Bright, all within the spirits and principles of the present invention, any modification, equivalent substitution, improvement and etc. done should be included in the present invention
Protection scope within.
Claims (6)
1. a kind of weaving active cationic dye, which is characterized in that have following general formula
Compound and its derivative
Object, wherein R1And R2It is any in H, Cl, Br or CN.
2. a kind of weaving active cationic dye according to claim 1, which is characterized in that have the following structure formula
Compound.
3. the preparation method based on weaving active cationic dye described in claim 1, which is characterized in that including following step
It is rapid: step 1, to N-ethylaniline hydroxyethylation, chlorination, amination, to obtain coupling component A；Step 2, by 4- nitroaniline and its spread out
After biological diazotising, after coupling component A coupling reaction, then through quaternized processing to get the compound and its derivative of logical formula (I)
Object.
4. the preparation method that active cationic dye is used in weaving according to claim 3, which is characterized in that even in step 2
Reaction is closed to carry out at 5-10 DEG C.
5. the tint applications based on weaving active cationic dye described in claim 1, which is characterized in that including following step
Rapid: according to bath raio 1:30-50, dye dosage is the 0.5-4% to fabric weight, and room temperature enters dye, and 1-2 DEG C/min is warming up to 60-70
DEG C, sodium carbonate 15-25g/L is added, continues to dye 40-60min, dye finishes, and washing is soaped, and washes, dyeing is completed in drying.
6. the tint applications that active cationic dye is used in weaving according to claim 5, which is characterized in that the cation
The color of reactive dye is from orange to red.
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| CN201910249350.4A CN109825110A (en) | 2019-03-29 | 2019-03-29 | A kind of weaving active cationic dye and preparation method thereof and tint applications |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114164687A (en) * | 2022-01-13 | 2022-03-11 | 常州纺织服装职业技术学院 | Cotton fabric cationic modifier and application thereof |
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|---|---|---|---|---|
| CN105585875A (en) * | 2015-11-30 | 2016-05-18 | 南京工业大学 | Di-cationic reactive dye for salt-free dyeing of cotton woven fabrics and preparation method thereof |
| CN107353671A (en) * | 2017-07-17 | 2017-11-17 | 南京工业大学 | A kind of azo structure contained active cationic dye and preparation method thereof |
| CN108047759A (en) * | 2017-12-26 | 2018-05-18 | 沈阳化工研究院有限公司 | A kind of epoxy type reactive disperse dyes and its preparation method and application |
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2019
- 2019-03-29 CN CN201910249350.4A patent/CN109825110A/en active Pending
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|---|---|---|---|---|
| CN105585875A (en) * | 2015-11-30 | 2016-05-18 | 南京工业大学 | Di-cationic reactive dye for salt-free dyeing of cotton woven fabrics and preparation method thereof |
| CN107353671A (en) * | 2017-07-17 | 2017-11-17 | 南京工业大学 | A kind of azo structure contained active cationic dye and preparation method thereof |
| CN108047759A (en) * | 2017-12-26 | 2018-05-18 | 沈阳化工研究院有限公司 | A kind of epoxy type reactive disperse dyes and its preparation method and application |
Non-Patent Citations (1)
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| CHUNLLIN ZHENG等: "Dyeing properties of novel electrolyte-free reactive dyes on cotton fibre", 《COLORATION TECHNOLOGY》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114164687A (en) * | 2022-01-13 | 2022-03-11 | 常州纺织服装职业技术学院 | Cotton fabric cationic modifier and application thereof |
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Application publication date: 20190531 |