CN105733301A - Positive ion reactive dye with m-aminoacetanilide as coupling component and preparation method and application of positive ion reactive dye - Google Patents
Positive ion reactive dye with m-aminoacetanilide as coupling component and preparation method and application of positive ion reactive dye Download PDFInfo
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- CN105733301A CN105733301A CN201610255044.8A CN201610255044A CN105733301A CN 105733301 A CN105733301 A CN 105733301A CN 201610255044 A CN201610255044 A CN 201610255044A CN 105733301 A CN105733301 A CN 105733301A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
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Abstract
The invention relates to a positive ion reactive dye with m-aminoacetanilide as a coupling component and a preparation method and application of the positive ion reactive dye. The structural formula is shown in the description, wherein R1 is H or Cl or NO2, R2 is H or CH3 or NO2, R3 is H or Cl or NO2 or OCH3, and R4 is H or Br. The preparation method includes the steps that dimethyl sulfate is added into an m-aminoacetanilide water solution dropwise, the mixture reacts at the temperature of 60-70 DEG C and is cooled to room temperature, concentrated sulfuric acid is added, an intermediate A is obtained after the reaction and added into a cyanuric chloride acetone solution dropwise, an intermediate B is obtained after the reaction, an m-aminoacetanilide diluted hydrochloric acid solution is added dropwise, and coupling component reaction liquid C is obtained after the reaction; diazo-reaction liquid of an amino aniline compound is added dropwise, then washing and drying are conducted after the reaction, and the positive ion reactive dye is obtained. The dye is applied to dyeing of single-component fiber fabric and one-bath process dyeing of fiber blended and interwoven multi-component fiber fabric, and the advantages of water saving, energy saving, ecological environmental protection and the like are achieved.
Description
Technical field
The invention belongs to Dyestuff synthesis and textile dyeing field, particularly to active cationic dye that a kind of coupling component is 3-acetylaminoaniline and its preparation method and application.
Background technology
Along with the continuous appearance of tencel, the exploitation of fabric fabric variety occurs like the mushrooms after rain.Multicomponent fiber blended, weaving face fabric that is that interweave integrates the advantage of multiple fiber, and its wearability is excellent, can meet different individual needs, be subject to the favor of consumers in general, it has also become the mainstream product in the market.Adopt the fabric of multiple fiber design, exploitation, it is possible to reach some chemical finishing and be beyond one's reach effect.As added the Lycra of 2-5% in cotton, wool fibre, it is possible to significantly improve natural fiber wrinkle resistance, wash and wear performance, reach easy maintenance, nurse simple purpose.Polyster fibre adds part chinlon, acetate fiber, is possible not only to improve the antistatic of fabric, soil release performance energy, it is also possible to improve fabric sheen.Multifilament blended product Colour Difference and functional finish technology are the quality assurances that such fabric is important.Due to the complicated component of multi-fiber fabric, dyeability and the physical and chemical performance of fiber are different, and therefore its dyeing processing technique is complicated, and energy consumption is big, and cost is high, and fiber has bigger damage.Different types of dyestuff is likely to can influence each other coloured light and fastness, it is difficult to obtain good Color.Such as tradition hair/nitrile blend fabric adopts and contaminates different fibers on different dyestuffs, the acrylon dye of positive ion, and the anionic dyes such as Pilus Caprae seu Ovis acid stain, acid mordant dye or amount of activated dyestuff, two types dyestuff is easy in electrostatic attraction formation color lake in dye bath, thus affecting dyeing quality and dyefastness.In order to avoid the generation in color lake, need to add substantial amounts of antisettling agent in dyeing course, which not only adds production cost and increase the burden of waste water.
Summary of the invention
The technical problem to be solved is to provide active cationic dye that a kind of coupling component is 3-acetylaminoaniline and its preparation method and application, this dyestuff is mainly used in acrylon, cellulose fibre, the dyeing of the one-component fiber such as protein fibre, Fypro, it is also possible to for acrylon/protein fibre, acrylon/cellulose fibre, acrylon/Fypro multicomponent fibre one-bath dyeing；There is the advantage such as water saving, energy-conservation, ecological, environmental protective.
The active cationic dye that a kind of coupling component is 3-acetylaminoaniline of the present invention, structural formula is:Wherein, R1=H, Cl or NO2；R2=H, CH3Or NO2；R3=H, Cl, NO2,OCH3；R4=H or Br.
The preparation method of the active cationic dye that a kind of coupling component is 3-acetylaminoaniline of the present invention, including:
(1) at 60～70 DEG C, dimethyl sulfate is added drop-wise in the aqueous solution of 3-acetylaminoaniline, reacts 11～13h, adding concentrated sulphuric acid after being cooled to room temperature, at 90～100 DEG C, reaction obtains intermediate A in 1～3 hour, i.e. 3-amino-N, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution；
(2) intermediate A in step (1) is slowly added dropwise in the acetone soln of Cyanuric Chloride, add trash ice and maintain reaction temperature at 0-5 DEG C, pH is that 3-5 reacts 3-5 hour, intermediate B need not be filtrated to get, i.e. 3-((4,6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
(3) dilute hydrochloric acid solution of 3-acetylaminoaniline is slowly added dropwise in the intermediate B to step (2), in pH=5～7, react 3～6 hours under 30～40 DEG C of conditions, without being filtrated to get coupling component reaction liquid C, i.e. 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
(4) there is diazo-reaction in the amino benzenes compounds containing amino under sodium nitrite/hydrochloric acid or sulphuric acid/nitrosyl sulfuric acid effect, obtain diazo-reaction liquid, under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to step (3) in the coupling reaction liquid C prepared, and with saturated sodium carbonate solution, pH value is adjusted to 5-7, react and be filtrated to get dyestuff in 4-12 hour, with a large amount of water flush cake vacuum drying.
In described step (1), the pH of the aqueous solution of 3-acetylaminoaniline is 7；At 65 DEG C, when pH=7, it is slowly added dropwise dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature.
In described step (1), the mol ratio of dimethyl sulfate and 3-acetylaminoaniline is 4:1.
In described step (2), intermediate A is 1:1.5 with the mol ratio of Cyanuric Chloride.
In described step (3), 3-acetylaminoaniline is 1:1 with the mol ratio of intermediate B.
In described step (4), the amino benzenes compounds of amino is at least one in meta-aminotoluene, P-nethoxyaniline, paranitroanilinum, 2,4-dichloroanilines, 2-chloro-4-nitroaniline, 2,4-dinitroanilines, bromo-4, the 6-dinitroanilines of 2-etc..
Described coupling component is the application of the active cationic dye of 3-acetylaminoaniline, for acrylon, cellulose fibre, the dyeing of the one-component fiber such as protein fibre, Fypro, it is also possible to for acrylon/protein fibre, acrylon/cellulose fibre, acrylon/Fypro multicomponent fibre one-bath dyeing.
Described dyeing is: adopt infusion process, dye dosage 0.5-5% (owf), bath raio 40:1, dyeing temperature 95 DEG C, 1-2 hour time.
Above fiber is had significantly high affinity by described dyestuff, and has every color fastness of excellence.
Beneficial effect
The active cationic dye of the present invention can be used not only for acrylon, cellulose fibre, the dyeing of the one-component fiber such as protein fibre, Fypro, can be used for the one-bath dyeing of acrylon/protein fibre, acrylon/cellulose fibre, acrylon/Fypro multi-fiber fabric, such that it is able to reduce the use of dye material, using water wisely and the saving energy, reduce the discharge of sewage simultaneously, eliminate the dyeing of multiple dyestuff many baths method and cause the flaw of staining, improve the quality of dyed fabric.
Accompanying drawing explanation
Fig. 1 is embodiment 1 cationic reactive dye infared spectrum.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is expanded on further.Should be understood that these embodiments are merely to illustrate the present invention rather than restriction the scope of the present invention.In addition, it is to be understood that after having read the content that the present invention lectures, the present invention can be made various changes or modifications by those skilled in the art, and these equivalent form of values fall within the application appended claims limited range equally.
Embodiment 1
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 0.01mol meta-aminotoluene is dissolved in 3ml hydrochloric acid and 10ml deionized water mixed solution, at 0-5 DEG C, is slowly added dropwise 0.69g30% sodium nitrite solution, and diazo-reaction 1 hour, add 0.2g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 5, sucking filtration after answering for anti-hour 4 hours, a large amount of water flush cake, vacuum drying obtains yellow cationic reactive dye, and structural formula is as follows:
Gained active cationic dye is carried out one-bath dyeing to stock-dyes such as acrylon, Pilus Caprae seu Ovis, silkworm silk, nylon and to multicomponent fibres such as acrylon/Pilus Caprae seu Ovis, acrylon/silkworm silk, acrylon/nylon.Wool fabric dyeing condition is illustrated: adopt infusion process, dye dosage 0.5-5% (owf), bath raio 40:1, dyeing temperature 95 DEG C, 1-2 hour time.Washing away as set and hydrolised dye after dyeing, then carry out indices test according to AATCC standard, soaping fastness can reach 5 grades, and fastness to rubbing is 4 grades, and fastness to perspiration is 5 grades, and sunlight fastness is 4 grades.
Gained active cationic dye carries out Infrared Characterization, and the spectrogram obtained is as shown in Figure 1.There is absworption peak near 3300cm-1 in-NH-, and C=O key absworption peak is at 1680cm-1,-N=N-is at 1600cm-1There is stretching vibration peak in place, and C=N is at 1500cm-1Place forms sharp-pointed stretching vibration peak, and C-Cl key absworption peak is at 810cm-1Place.
Embodiment 2
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 1.23g P-nethoxyaniline is dissolved in 2.75ml hydrochloric acid and 10ml deionized water mixed solution, at 0-5 DEG C, fast drop 5ml30% sodium nitrite solution, diazo-reaction 0.5 hour, add 0.21g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 5-6, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain yellow cationic reactive dye in 24 hours, and structural formula is as shown in table 1.
Embodiment 3
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 1.38g meta nitro aniline is dissolved in 2.75ml hydrochloric acid and 20ml deionized water mixed solution, at 0-5 DEG C, fast drop 5ml30% sodium nitrite solution, and diazo-reaction 1 hour, add 0.21g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 5, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain yellow cationic reactive dye in 24 hours, and structural formula is as shown in table 1.
Embodiment 4
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 1.38g paranitroanilinum is dissolved in 2.75ml hydrochloric acid and 20ml deionized water mixed solution, at 0-5 DEG C, fast drop 5ml30% sodium nitrite solution, and diazo-reaction 1 hour, add 0.21g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 5, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain orange-yellow active cationic dye in 24 hours, and structural formula is as shown in table 1.
Embodiment 5
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 1.62g2,4-dichloroaniline is dissolved in 2.75ml hydrochloric acid and 20ml deionized water mixed solution, at 0-5 DEG C, fast drop 5ml30% sodium nitrite solution, and diazo-reaction 1 hour, add 0.21g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 5, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain pink active cationic dye for 24 hours, and structural formula is as shown in table 1.
Embodiment 6
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, chloro-for 1.72g2-4-nitroaniline is dissolved in 5ml concentrated sulfuric acid solution, at 0-5 DEG C, is slowly added dropwise 3ml nitrosyl sulfuric acid solution, and diazo-reaction 2 hours, add 0.2g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 4-5, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain red active cationic dye for 24 hours, and structural formula is as shown in table 1.
Embodiment 7
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 1.83g2,4-dinitroaniline is dissolved in 5ml concentrated sulfuric acid solution, at 0-5 DEG C, is slowly added dropwise 3ml nitrosyl sulfuric acid solution, and diazo-reaction 2 hours, add 0.2g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 4-5, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain red active cationic dye for 24 hours, and structural formula is as shown in table 1.
Embodiment 8
A, 15g 3-acetylaminoaniline is dissolved in 100ml deionized water, at 65 DEG C, when pH=7, it is slowly added dropwise 40ml dimethyl sulfate to 3-acetylaminoaniline aqueous solution, after reacting 12 hours, is cooled to room temperature, add 10ml concentrated sulphuric acid, at 90 DEG C, deacetylation obtains intermediate 3-amino-N after 1 hour, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution, it is not necessary to filter and be directly used in next step；
B, 2.77g Cyanuric Chloride is dissolved in 70ml acetone, and add the making beating of 10g trash ice, the intermediate 3-amino-N by the NaOH solution of 2mol/L prepared by step a, N, after N-trimethylbenzene methylsulfuric acid ammonium salt solution pH value is adjusted to neutrality, take its 25ml to be slowly added dropwise to the acetone soln of Cyanuric Chloride, and add trash ice maintenance reaction temperature at 0-5 DEG C, use saturated NaCO3Solution controls pH value in reaction 4, need not be filtrated to get a condensation intermediate 3-((4,6-bis-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride after reacting 3 hours；
C, 1.50g 3-acetylaminoaniline is dissolved in 10ml dilute hydrochloric acid solution and is slowly added dropwise to the step b condensation intermediate 3-((4 prepared, 6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, in N-Trimethyl Phenyl ammonium chloride solution, at pH=6, react 5 hours under 35 DEG C of conditions, without being filtrated to get coupling component 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
D, 2.62g2,4-dinitro-6-bromaniline is dissolved in 5ml concentrated sulfuric acid solution, at 0-5 DEG C, is slowly added dropwise 3ml nitrosyl sulfuric acid solution, and diazo-reaction 2 hours, add 0.2g sulfamic acid and eliminate excessive nitrous acid.Under 0-5 DEG C of condition, the diazo component reactant liquor obtained is slowly added dropwise to the step c coupling reaction liquid prepared, and with saturated sodium carbonate solution, pH value is adjusted to 4-5, sucking filtration after reacting 4 hours, a large amount of water flush cake, 30 DEG C of vacuum dryings obtain red active cationic dye for 24 hours, and structural formula is as shown in table 1.
Table 1
Claims (9)
1. coupling component is an active cationic dye for 3-acetylaminoaniline, and structural formula is:Wherein, R1=H, Cl or NO2；R2=H, CH3Or NO2；R3=H, Cl, NO2,OCH3；R4=H or Br.
2. coupling component is a preparation method for the active cationic dye of 3-acetylaminoaniline, including:
(1) at 60～70 DEG C, dimethyl sulfate is added drop-wise in the aqueous solution of 3-acetylaminoaniline, reacts 11～13h, concentrated sulphuric acid is added after being cooled to room temperature, at 90～100 DEG C, reaction obtains intermediate 3-amino-N, N, N-trimethylbenzene methylsulfuric acid ammonium salt solution for 1～3 hour；
(2) being added drop-wise in the acetone soln of Cyanuric Chloride by the intermediate A in step (1), pH is 3-5,0-5 DEG C and reacts 3-5 hour, obtain intermediate 3-((4,6-bis-chloro-1,3,5-triazine-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
(3) dilute hydrochloric acid solution of 3-acetylaminoaniline is dropped in the intermediate B in step (2), in pH=5～7, react 3～6 hours under 30～40 DEG C of conditions, obtain coupling component reactant liquor, i.e. 3-((4-((3-acetanilide) amino)-6-chloro-1,3,5-triazines-2-yl) amino)-N, N, N-Trimethyl Phenyl ammonium chloride；
(4) adding in the reaction liquid C in step (3) by the diazo-reaction drop of the amino benzenes compounds of amino, regulating pH is 5～7, reacts 4～2 hours, rinses, dry, obtains the active cationic dye that coupling component is 3-acetylaminoaniline.
3. a kind of coupling component according to claim 2 is the preparation method of the active cationic dye of 3-acetylaminoaniline, it is characterised in that in described step (1), the pH of the aqueous solution of 3-acetylaminoaniline is 7.
4. a kind of coupling component according to claim 2 is the preparation method of the active cationic dye of 3-acetylaminoaniline, it is characterised in that in described step (1), dimethyl sulfate and 3-acetylaminoaniline mol ratio are 4:1.
5. a kind of coupling component according to claim 2 is a preparation method for the active cationic dye of glycyl propylamine, it is characterised in that in described step (2), intermediate A is 1:1.5 with the mol ratio of Cyanuric Chloride.
6. a kind of coupling component according to claim 2 is the preparation method of the active cationic dye of 3-acetylaminoaniline, it is characterised in that in described step (3), 3-acetylaminoaniline is 1:1 with the mol ratio of intermediate B.
7. a kind of coupling component according to claim 2 is the preparation method of the active cationic dye of 3-acetylaminoaniline, it is characterized in that, in described step (4) amino benzenes compounds of amino be meta-aminotoluene, P-nethoxyaniline, paranitroanilinum, 2, the chloro-4-nitroaniline of 4-dichloroaniline, 2-, 2, at least one in bromo-4, the 6-dinitroanilines of 4-dinitroaniline, 2-.
8. a coupling component as claimed in claim 1 is the application of the active cationic dye of 3-acetylaminoaniline, it is characterized in that, it is applied to acrylon, cellulose fibre, the dyeing of protein fibre or Fypro homofil fabric, the one-bath dyeing of fiber blend and intertexture multi-fiber fabric.
9. a kind of coupling component according to claim 8 is the application of the active cationic dye of 3-acetylaminoaniline, it is characterised in that described dyeing is: adopt infusion process, dye dosage 0.5-5% (owf); bath raio 40:1, dyeing temperature 95 DEG C, 1-2 hour time.
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