CN105086509B - A kind of cross-linking reactive disperse dyes compound and its preparation and application - Google Patents
A kind of cross-linking reactive disperse dyes compound and its preparation and application Download PDFInfo
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Abstract
The present invention relates to a kind of cross-linking reactive disperse dyes compound and its preparation and application, disperse dye compound Formula is：Preparation method：Preparation, diazotising and the coupling reaction of coupling component, the amino of the aminated compounds containing aminobenzene is replaced by active group in synthesized compound structure, active group is the hydroxypropyl of 3 chlorine 2, and the substituent can form crosslinkable epoxy ethyl active group in the basic conditions.Applied to ink-jet ink.Invention it is a kind of can simultaneously on polyester fiber and cotton fiber stamp cross-linking reactive disperse dyes compound, and stamp of the ink-jet ink applied to the blend fabric such as polyester-cotton blend is prepared into, solve poor polyester cotton pigment printing feel, poor washing fastness and mixed dye printing technology long flow path, the shortcomings of the mutual staining of dyestuff is serious.
Description
Technical field
The present invention is Application No. 201410397890.4, denomination of invention：A kind of cross-linking reactive disperse dyes compound
And its preparation and application, the applying date are in August, 2014 divisional application of 13 days.
Background technology
With the fast development that computer technology is applied in textile field, the application field of inkjet technology mainly expands
Open up as in terms of three below：Desktop jet printing, air brushing jet printing and fabric jet printing.The purpose of the inkjet printing of fabric
It is that instead of traditional printing technique：, can be by graphical design, sample scaling with beating because ink jet printing device can be combined with computer
Print is combined, and can meet the requirement of short route, small lot, multi items, or even can accomplish to customize image.In particular with spray
Continuous renewal, the continuous improvement of dyestuff performance and the improvement of ink performance of ink-printed equipment, ink-jet printed technology are caused
The extensive concern of dyeing personage.
The colouring agent used in ink-jet ink, mainly there is two kinds of pigment and dyestuff.Pigment ink have technique it is simple,
Cost is low and the advantages of to fabric non-selectivity, but due to Boardy Feeling, vividness difference and the low shortcoming of fastness to rubbing, it is main to use
In outdoor air brushing.Type of dye ink is mainly used in the stamp of fabric, and various dyestuffs can be used, presently mainly be knitted for cotton
The reactive dye of thing and the disperse dyes for closing fine fabric.The advantage of type of dye ink mainly has：One is bright in colour, stabilization
Property is good, is not easily blocked shower nozzle；Two be that dye chromatography used is complete, and range of choice is wide, relative inexpensiveness；Three be due to half with
On composition be water, so meeting environmental requirement.Therefore, dye-type ink-jet ink is always the staple product in market, with not
Alternative status.
Polyester cotton dye printing is more complicated, is typically the dye printing to every kind of fiber respective type.Wash
Synthetic fibre fabric coloring is mainly disperse dyes, and bafta can use the coloring such as reactive dye, reducing dye, soluble vat dye.
During stamp, most cotton dye is not adsorbed by polyester fiber, and a considerable amount of disperse dyes are to cotton fiber
Staining.Therefore, in polyester cotton stamp, it is necessary to fully clean to remove staining in the disperse dyes of cotton fiber, but still
The unavoidable staining for occurring fabric bottom surface.When polyester cotton blending ratio changes, the mixture of different type dyestuff is in color compatibility
There is also difficulty in property.Also, color of the different type dyestuff on each on the fiber that contaminates in coloured light, color depth and fastness very
It is difficult consistent.Accordingly, it is capable to which these problems can be overcome to the cross-linking reactive disperse dyes of two kinds of fiber colourings simultaneously.
The ink-jet printed technology of polyester cotton is in addition to selecting suitable dyestuff, and another key issue is the system of ink
It is standby.Due to being sprayed using nozzle, it is necessary to many factors of ink be considered, wherein topmost physical and chemical performance index：Grain
Footpath, viscosity, surface tension, electrical conductivity etc..
The content of the invention
The technical problems to be solved by the invention are to provide a kind of cross-linking reactive disperse dyes compound and its application, should
The purpose of invention be invention it is a kind of can simultaneously on polyester fiber and cotton fiber stamp cross-linking reactive disperse dyes compound,
And stamp of the ink-jet ink applied to blend fabric such as polyester-cotton blend is prepared into, solve polyester cotton pigment printing feel
Difference, washing fastness difference and mixed dye printing technology long flow path, the shortcomings of the mutual staining of dyestuff is serious.
A kind of cross-linking reactive disperse dyes compound of the present invention, the disperse dye compound Formula is：
In one or more；
Wherein
R1=NO2, Cl, Br, CN, CH3；
R2=H, OCH3, OCH2CH3, Br, Cl, CN；
R3=H, CH3, NO2, Cl, Br；
R4=H, OCH3, OCH2CH3, Br, Cl, CN；
R5=H, CH3, OCH3, OC2H5, OC2H4OCH3；
R6=H, OCH3, NHCOCH3, NHCOC2H5, SO2CH3；
R7=R8=H, CH2CH(OH)CH2Cl, CH2CH(OH)CH2Br, CH3, CH2CH3, C2H4OH, C2H4CN,
C2H4OCOCH3；
X1=X2=H, NO2, Cl；
X3=H, Cl；
X4=X5=H, OCH3, Cl.
A kind of preparation method of cross-linking reactive disperse dyes compound of the present invention, including：
(1) preparation of coupling component：Amino benzenes compounds containing amino, epoxychloropropane, catalyst are mixed, stirred molten
Solution, reaction, obtains coupling component reaction solution；The mol ratio of amino benzenes compounds and epoxychloropropane wherein containing amino is 1.0:
8, the consumption of catalyst is 2% of the amino benzenes compounds quality containing amino, and reaction temperature is 30-50 DEG C, and the reaction time is 30-
36h；
(2) diazotising and coupling reaction：The compound with amino is in natrium nitrosum/hydrochloric acid or salt on phenyl ring or heterocycle
Acid/nitrosyl sulfuric acid effect is lower to occur diazo-reaction, obtains diazo-reaction liquid；Wherein in diazo-reaction, containing amino
The mol ratio of phenyl amines or heterocycle compound, natrium nitrosum and hydrochloric acid is 1：1.01~1.10：2.5~3.0, diazotising temperature
0~5 DEG C, 1~2h of reaction time；Or phenyl amines or heterocycle compound containing amino, the mol ratio of nitrosyl sulfuric acid and sulfuric acid
For 1：1.01~1.10：3.0~8.0, -5~5 DEG C of diazotising temperature, 4~5h of reaction time；Wherein R1, R2, R3, R4, R5Ibid；
(3) above-mentioned coupling component reaction solution is completely dissolved in acetum, under agitation, adds diazotising anti-
Liquid is answered to carry out coupling reaction, reaction temperature is 5-15 DEG C, and the reaction time is 3-4h；After reaction completely, at 60-70 DEG C, 1h is heated
Afterwards, suction filtration, is washed, drying；R in coupling reaction product7And R8At least one position introduces CH2CH(OH)CH2Cl groups.
Catalyst is benzyltriethylammoinium chloride or lithium bromide in the step (1).
A kind of application of cross-linking reactive disperse dyes compound of the present invention, it is characterised in that：The disperse dyes
Compound is applied to ink-jet ink.
The ink-jet ink includes：Cross-linking disperse dye compound, dispersant, organic solvent, surfactant, anti-corrosion
Agent and defoamer.
The ink-jet ink, by the percentage of ink gross mass, cross-linking reactive disperse dyes mass content 1~15%；
Dispersant mass content 1~15%；Organic solvent mass content 15~35%；Surfactant qualities content 1~5%；Conductance
Rate conditioning agent mass content 1~5%；Preservative mass content 0.5~1%；Defoamer mass content 0.5~1%；Deionized water
For surplus.
The dispersant is MF, 85A, NNO one or more of；Organic solvent is glycerine, ethylene glycol, butanone, Isosorbide-5-Nitrae-fourth
One or more in glycol, diethylene glycol, diglycol, Diethylene Glycol, diethylene glycol monoethyl ether；Surfactant
For the one or more in OP-7, OP-10, OP-15, paregal O；Preservative is standby anti-many D2 or preservative SJ1006；Froth breaking
Agent is Z-8415 or Z-8410.
The ink-jet ink is used for the spray printing of the ink-jet printed fabric of polyester cotton, is specially：Fabric is entered first
Row pretreatment, pretreated fabric carries out directly ink-jet printed, PRINTED FABRIC progress fixation at ambient temperature.
The pretreatment condition is that sodium carbonate is 30~40g/L, and urea is 80~100g/L, and sodium alginate original paste consumption is
(40g sodium alginates, which are dissolved in 960g water, prepares former paste, 40g/L) is 8~25g/L, and pick-up is 70%, then in 104 DEG C of bars
5min is dried under part；Color fixing condition is progress decatize under the conditions of 130~165 DEG C or bakes 10~15min.
The cross-linking reactive disperse dyes of the present invention can be applied in ink-jet ink.Specific applying step is as follows：
The preparation of mill base：
(1) dyestuff and dispersant 1:After 1 (mass ratio) is fully ground, adds organic solvent, part surface activating agent and go
The each components such as ionized water, are fully sanded, obtain a slurry.(2) a slurry is subjected to homogeneous experiment with high pressure homogenizer, weight
It is multiple three times, obtain secondary slurry.(3) secondary slurry is subjected to homogeneous with Microfluidizer, in triplicate, obtains three slurries
Material, as mill base.
The preparation of ink：
(1) electrical conductivity conditioning agent, preservative and remaining surfactant and deionized water are added to gained ink color
In slurry, it is stirred well under normal temperature room temperature condition uniform；(2) again after centrifuge certain time, upper strata slurry is taken out
Expect mixture；(3) mixture is stood into two weeks curing；(4) finished product is obtained with 250nm membrane filtration；(5) after detection curing
Ink mixture indices.
In the preparation process of the mill base, cross-linking reactive disperse dyes mass content 1-15%；Dispersant mass content
For the 1-15% of ink gross mass；Organic solvent content 15-35%；Surfactant qualities content 0.18-4%；Defoamer matter
Measure content 0.5-1%；Deionized water quality content 10-50%.Mass content is to account for ink gross mass percentage composition at this.
In the preparation process of the mill base, sand milling condition is：Rotating speed is 1000-5000r/min；Time is 4-8h；Zirconium pearl d
For 1.2mm and 1.5mm；Zirconium pearl volumetric filling ratio is 40-60%.
In the preparation process of the mill base, high-pressure homogeneous condition is：Pressure is 20-80MPa；Number of times is 3 times.
In the preparation process of the mill base, microjet processing condition is：Pressure is 120-300MPa；Flow is 50ml/
min；Number of times is 3 times.
In the ink preparation process, preservative mass content is the 0.5-1% of ink gross mass；Electrical conductivity conditioning agent matter
Measure the 1-5% that content is ink gross mass；Surfactant qualities content is the 0.02-1% of ink gross mass；Surplus for go from
Sub- water quality.
In the preparation process of the mill base, centrifugal condition is：Rotating speed is 6000-12000r/min；Time is 30-60min；
In the ink preparation process, indices are (25 DEG C)：Particle diameter is 100-250nm；Viscosity is 1.5-3mPa
s；Surface tension 20-40mN/m；Electrical conductivity is 1000-1500 μ s/cm.
Beneficial effect
The purpose of the present invention be invention it is a kind of can simultaneously on polyester fiber and cotton fiber stamp cross-linking active dispersal
Dye composition, and stamp of the ink-jet ink applied to blend fabric such as polyester-cotton blend is prepared into, solve polyester cotton
Pigment printing feel is poor, washing fastness difference and mixed dye printing technology long flow path, the shortcomings of the mutual staining of dyestuff is serious；
The cross-linking reactive disperse dyes chromatogram that this patent is related to is complete, can make yellow, orange, red, purple,
The ink of blueness and green, while fastness is good, the black of high pitch black degree can be gone out with blending by carrying out a certain proportion of compounding
Dyestuff；
The ink of the present invention has a good printing fluency, and is printed upon on fabric and has lovely luster, sun-resistant,
The advantages of water-fastness, fastness to rubbing is good, available for the ink-jet printed of textile.
Brief description of the drawings
Fig. 1 is Dyestuff synthesis flow chart；
Fig. 2 is the infrared spectrum of the dyestuff of example 1；
Fig. 3 is the infrared spectrum of the dyestuff of example 2；
Fig. 4 is the infrared spectrum of the dyestuff of example 3；
Fig. 5 is the infrared spectrum of the dyestuff of example 4；
Fig. 6 is the infrared spectrum of the dyestuff of example 5；
Fig. 7 is the infrared spectrum of the dyestuff of example 6；
Fig. 8 is the infrared spectrum of the dyestuff of example 7.
Embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention
Rather than limitation the scope of the present invention.In addition, it is to be understood that after the content of the invention lectured has been read, people in the art
Member can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited
Scope.
Embodiment 1
Synthesize target：
Raw material includes meta nitro aniline, epoxychloropropane, aniline, benzyltriethylammoinium chloride, hydrochloric acid, natrium nitrosum etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 18.63g are sequentially added in coupling reaction kettle pure
Spend the aniline and 0.36g benzyltriethylammoinium chlorides for 100%, stirring is to being completely dissolved.Keep rotating after room temperature reaction 36h and steam
Unnecessary epoxychloropropane is sent, there is the generation of taupe dope, the acetic acid of 50ml 30% is added and stirs stand-by to being completely dissolved.
Diazo-reaction：Sequentially added in diazo-reaction kettle the meta nitro anilines of 27.6g 100%, 500ml water and
The hydrochloric acid heating stirrings of 50ml 36% are to being completely dissolved, and chuck leads to condensed water, and 47.33g is slowly added dropwise under 0-5 DEG C and normal pressure
30% sodium nitrite solution, keeps diazo-reaction 1h under 0-5 DEG C and condition of normal pressure, adds sulfamic acid and eliminates excessive nitrous
Acid.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 2
Synthesize target：
Raw material includes paranitroanilinum, epoxychloropropane, 3- amino-4-methoxyacetanilides, benzyl triethyl ammonium chlorination
Ammonium, hydrochloric acid, natrium nitrosum etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 36g purity are sequentially added in coupling reaction kettle
For 100% 3- amino-4-methoxyacetanilides and 0.72g benzyltriethylammoinium chlorides, stirring is to being completely dissolved.Keep room
Rotary evaporation goes out unnecessary epoxychloropropane after temperature reaction 36h, has dark-grey brown viscous thing to generate, adds the acetic acid of 50ml 30%
Stirring is stand-by to being completely dissolved.
Diazo-reaction：Sequentially added in diazo-reaction kettle the meta nitro anilines of 27.6g 100%, 500ml water and
The hydrochloric acid heating stirrings of 50ml 36% are to being completely dissolved, and chuck leads to condensed water, and 47.33g is slowly added dropwise under 0-5 DEG C and normal pressure
30% sodium nitrite solution, keeps diazo-reaction 1h under 0-5 DEG C and condition of normal pressure, adds sulfamic acid and eliminates excessive nitrous
Acid.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 3
Synthesize target：
Raw material include bromo- 4, the 6- dinitros-aniline of 2-, epoxychloropropane, an antifebrin, benzyltriethylammoinium chloride,
Sulfuric acid and nitrosyl sulfuric acid etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 30g purity are sequentially added in coupling reaction kettle
For antifebrin and 0.6g benzyltriethylammoinium chlorides between 100%, stirring is to being completely dissolved.Revolved after keeping room temperature reaction 36h
Turn to evaporate unnecessary epoxychloropropane, there is the generation of taupe dope, add the acetic acid of 50ml 30% and stir to being completely dissolved and treat
With.
Diazo-reaction：Sequentially added in diazo-reaction kettle the bromo- 4,6- dinitros-aniline of 52.404g 100%2-,
103.6g98% sulfuric acid is stirred under the conditions of 20-30 DEG C to being completely dissolved, and 63.5g 40% nitrosyl sulfuric acid is slowly added dropwise, and is risen
Temperature adds sulfamic acid and eliminates excessive nitrous acid to 50-55 DEG C of insulation reaction 1h.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 4
Synthesize target：
Raw material includes bromo- 4, the 6- dinitros-aniline of 2-, epoxychloropropane, 3- amino-4-methoxyacetanilides, benzyl
Triethyl ammonium chloride, sulfuric acid and nitrosyl sulfuric acid etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 36g purity are sequentially added in coupling reaction kettle
For 100% 3- amino-4-methoxyacetanilides and 0.72g benzyltriethylammoinium chlorides, stirring is to being completely dissolved.Keep room
Rotary evaporation goes out unnecessary epoxychloropropane after temperature reaction 36h, there is the generation of taupe dope, adds the acetic acid of 50ml 30% and stirs
Mix stand-by to being completely dissolved.
Diazo-reaction：Sequentially added in diazo-reaction kettle the bromo- 4,6- dinitros-aniline of 52.404g 100%2-,
103.6g98% sulfuric acid is stirred under the conditions of 20-30 DEG C to being completely dissolved, and 63.5g 40% nitrosyl sulfuric acid is slowly added dropwise, and is risen
Temperature adds sulfamic acid and eliminates excessive nitrous acid to 50-55 DEG C of insulation reaction 1h.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 5
Synthesize target：
Raw material includes 3- amino -5- nitros benzisothiazole, epoxychloropropane, aniline, benzyltriethylammoinium chloride, sulphur
Acid, nitrosyl sulfuric acid etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 18.63g are sequentially added in coupling reaction kettle pure
Spend the aniline and 0.36g benzyltriethylammoinium chlorides for 100%, stirring is to being completely dissolved.Keep rotating after room temperature reaction 36h and steam
Unnecessary epoxychloropropane is sent, there is the generation of taupe dope, the acetic acid of 50ml 30% is added and stirs stand-by to being completely dissolved.
Diazo-reaction：It is 100% that the concentrated sulfuric acids of 178g 98% and 39g purity are sequentially added in diazo-reaction kettle
3- amino -5- nitro benzisothiazoles, after 3- amino -5- nitro benzisothiazoles are completely dissolved, chuck leads to chilled brine,
It is slowly added dropwise under -5~0 DEG C and normal pressure after 63.5g 40% nitrosyl sulfuric acid, completion of dropping and is slowly added dropwise 39g's 100%
Propionic acid, keeps diazo-reaction under -5~0 DEG C and condition of normal pressure, and the diazotising time is 4h, adds sulfamic acid and eliminates excess
Nitrous acid.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 6
Synthesize target：
Raw material include 3- amino -5- nitros benzisothiazole, epoxychloropropane, an antifebrin, benzyl triethyl ammonium chlorination,
Sulfuric acid, nitrosyl sulfuric acid etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 30g purity are sequentially added in coupling reaction kettle
Aniline and 0.6g benzyltriethylammoinium chlorides for 100%, stirring is to being completely dissolved.Keep rotary evaporation after room temperature reaction 36h
Go out unnecessary epoxychloropropane, there is the generation of taupe dope, add the acetic acid of 50ml 30% and stir stand-by to being completely dissolved.
Diazo-reaction：It is 100% that the concentrated sulfuric acids of 178g 98% and 39g purity are sequentially added in diazo-reaction kettle
3- amino -5- nitro benzisothiazoles, after 3- amino -5- nitro benzisothiazoles are completely dissolved, chuck leads to chilled brine,
It is slowly added dropwise under -5~0 DEG C and normal pressure after 63.5g 40% nitrosyl sulfuric acid, completion of dropping and is slowly added dropwise 39g's 100%
Propionic acid, keeps diazo-reaction under -5~0 DEG C and condition of normal pressure, and the diazotising time is 4h, adds sulfamic acid and eliminates excess
Nitrous acid.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 7
Synthesize target：
Raw material includes 3- amino -5- nitros benzisothiazole, epoxychloropropane, 3- amino-4-methoxyacetanilides, benzyl
The chlorination of base triethyl group, sulfuric acid, nitrosyl sulfuric acid etc..
The preparation of coupling component：The epoxychloropropane of 148.56g 100%, 36g purity are sequentially added in coupling reaction kettle
For 100% 3- amino-4-methoxyacetanilides and 0.72g benzyltriethylammoinium chlorides, stirring is to being completely dissolved.Keep room
Rotary evaporation goes out unnecessary epoxychloropropane after temperature reaction 36h, there is the generation of taupe dope, adds the acetic acid of 50ml 30% and stirs
Mix stand-by to being completely dissolved.
Diazo-reaction：It is 100% that the concentrated sulfuric acids of 178g 98% and 39g purity are sequentially added in diazo-reaction kettle
3- amino -5- nitro benzisothiazoles, after 3- amino -5- nitro benzisothiazoles are completely dissolved, chuck leads to chilled brine,
It is slowly added dropwise under -5~0 DEG C and normal pressure after 63.5g 40% nitrosyl sulfuric acid, completion of dropping and is slowly added dropwise 39g's 100%
Propionic acid, keeps diazo-reaction under -5~0 DEG C and condition of normal pressure, and the diazotising time is 4h, adds sulfamic acid and eliminates excess
Nitrous acid.
Coupling reaction：Coupling component bath on the rocks is cooled to 0~5 DEG C, by the slow dropwise addition into coupling component of diazol, side drop
Edged adds substantial amounts of mixture of ice and water into coupling reaction liquid.After diazol addition is finished, 10~15 DEG C of reaction 3-4h are kept,
With H acid detection diazol response situations.After completion of the reaction, suction filtration, massive laundering, drying.
The preparation of mill base：15g dyestuff filter-cakes are fully ground with 15g Dispersant MFs, 10g BDOs, 10g is added
Diethylene Glycol, 3g surfactants paregal O and 40g deionized waters are sufficiently mixed.100ml 1.2mm zirconium pearls are added to exist
Zirconium pearl is filtered out after 6h is sanded under conditions of 4000r/min, a slurry is produced.High-pressure homogeneous 3 under the conditions of pressure is 60MPa
It is secondary, obtain secondary slurry.Microjet homogeneous 3 times, is obtained three times under the conditions of processing flow is 50ml/min, 120~300MPa
Slurry, as mill base.
The preparation of ink：The standby anti-many D2 of 1g preservatives, 1g defoamers Z-8415,2g electrical conductivity conditioning agent are added into mill base
Ethylenediamine tetra-acetic acid；0.02g surfactant paregal Os；Surplus is deionized water quality.Fully stirred under normal temperature room temperature condition
Mix to uniform, then 30min is centrifuged under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood into two weeks ripe
Change, finished product is obtained with 250nm membrane filtration.Ink mixture indices after finally detection curing：Particle diameter is 200nm；Viscosity
For 2.0mPas；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Spray printing of the ink on polyester cotton：Fabric is pre-processed first：Sodium carbonate is 35g/L, and urea is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Fabric is dried under the conditions of 104 DEG C, is entered at ambient temperature
Row is directly ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Table 1：1-7 dyestuffs performance of the embodiment of the present invention and printing performance compare
| 1 | 2 | 3 | 4 | 5 | 6 | 7 | |
| Dye productivity (%) | 83 | 88 | 93 | 95 | 81 | 86 | 89 |
| Fusing point (DEG C) | 122-124 | 138-140 | 174-176 | 182-184 | 208-210 | 222-224 | 232-234 |
| λmax(nm) | 478 | 486 | 546 | 586 | 597 | 602 | 635 |
| ε(L mol-1cm-1) | 29625 | 30413 | 32714 | 37185 | 43619 | 50896 | 57806 |
| Color effects | Yellow | It is orange | It is red | Purple | Blueness | Blueness | Green |
| Wash (level) | 4 | 4 | 4-5 | 4-5 | 4-5 | 4-5 | 4-5 |
| Unlubricated friction (level) | 4 | 4 | 4 | 4 | 4-5 | 4-5 | 4-5 |
| It is wet to rub (level) | 3-4 | 3-4 | 4 | 4 | 4 | 4 | 4 |
| Distil (level) | 4-5 | 4-5 | 4-5 | 5 | 5 | 5 | 5 |
| Exposure to Sunlight (level) | 4 | 4-5 | 4-5 | 4-5 | 4-5 | 4-5 | 4-5 |
Note：Maximum absorption wavelength λ max and molar extinction coefficient ε tests are using acetone as solvent.
Claims (2)
1. a kind of preparation method of cross-linking reactive disperse dyes compound, including：
(1) amino benzenes compounds containing amino, epoxychloropropane, catalyst are mixed, stirring and dissolving, reaction obtains coupling group
Divide reaction solution；The mol ratio of amino benzenes compounds and epoxychloropropane wherein containing amino is 1.0:8, the consumption of catalyst be containing
The 2% of the amino benzenes compounds quality of amino, reaction temperature is 30-50 DEG C, and the reaction time is 30-36h；
(2) the generation diazotising under natrium nitrosum/hydrochloric acid or sulfuric acid/nitrosyl sulfuric acid effect of the heterocycle compound containing amino is anti-
Should, obtain diazo-reaction liquid；Wherein in diazo-reaction, heterocycle compound, natrium nitrosum and hydrochloric acid containing amino rub
You are than being 1：1.01~1.10：2.5~3.0,0~5 DEG C of diazotising temperature, 1~2h of reaction time；Or the heterocyclic containing amino
The mol ratio of compound, nitrosyl sulfuric acid and sulfuric acid is 1：1.01~1.10：3.0~8.0, -5~5 DEG C of diazotising temperature, during reaction
Between 4~5h；
(3) above-mentioned coupling component reaction solution is completely dissolved in acetum, under agitation, adds diazo-reaction liquid
Coupling reaction is carried out, reaction temperature is 5-15 DEG C, and the reaction time is 3-4h；After reaction completely, at 60-70 DEG C, after heating 1h, take out
Filter, is washed, drying；Wherein disperse dye compound Formula is：
Wherein
R5=H, CH3, OCH3OC2H5, OC2H4OCH3；
R6=H, OCH3, NHCOCH3, NHCOC2H5, SO2CH3；
R7=R8=CH2CH(OH)CH2Cl；
X3=H, Cl；X1、X2For one kind in H, NO2, Cl.
2. a kind of preparation method of cross-linking reactive disperse dyes compound according to claim 1, it is characterised in that：Institute
It is benzyltriethylammoinium chloride or lithium bromide to state catalyst in step (1).
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| CN107858839A (en) * | 2017-10-26 | 2018-03-30 | 卢梅雅 | A kind of green disperse dye composition and its application in woolen dyed |
| CN109440490B (en) * | 2018-10-12 | 2021-01-01 | 山东理工大学 | Lactic acid ester type disperse dye with azo structure for dyeing polylactic acid fiber, and preparation method and dyeing process thereof |
| CN110643197B (en) * | 2019-10-10 | 2020-11-27 | 济南大学 | Disperse black dye composition, disperse black dye and preparation method and application thereof |
| CN114350210A (en) * | 2022-02-24 | 2022-04-15 | 盐城工业职业技术学院 | Reactive disperse dye ink for cloth painting water color pen |
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| CN105086509A (en) | 2015-11-25 |
| CN105176133A (en) | 2015-12-23 |
| CN104194381A (en) | 2014-12-10 |
| CN104194381B (en) | 2017-01-11 |
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