CN104194381B - Crosslinkable active disperse dye compound as well as preparation method and application thereof - Google Patents
Crosslinkable active disperse dye compound as well as preparation method and application thereof Download PDFInfo
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- CN104194381B CN104194381B CN201410397890.4A CN201410397890A CN104194381B CN 104194381 B CN104194381 B CN 104194381B CN 201410397890 A CN201410397890 A CN 201410397890A CN 104194381 B CN104194381 B CN 104194381B
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Abstract
The invention relates to a crosslinkable active disperse dye compound as well as a preparation method and application thereof. A structural formula of the disperse dye compound is one or more as shown in the specification. The preparation method of the crosslinkable active disperse dye compound comprises the following steps: preparing coupling components, carrying out diazotization and coupling reaction, wherein amino of aminoaniline-containing compounds in the synthesized compound structure is substituted by an active group which is 3-chloro-2-hydroxypropyl, and the substituent group can be formed into a crosslinkable epoxy ethyl active group under an alkaline condition. The crosslinkable active disperse dye compound is applied to inkjet ink. The crosslinkable active disperse dye compound is capable of printing on polyester fibers and cotton fibers at the same time, and prepared into inkjet ink for being applied to printing of blended fabrics such as polyester cotton, so that the defect that the cotton-polyester blended fabric paint is poor in hand feeling during printing, poor in washing fastness, long in mixed dye printing process flow and severe in mutual-staining of dyes is solved.
Description
Technical field
The invention belongs to dye composition and preparation thereof and application, particularly to a kind of cross-linking reactive disperse dyes
Compound and preparation thereof and application.
Background technology
The fast development applied in textile field along with computer technology, the application of inkjet technology mainly expands
Exhibition is three below aspect: 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: owing to ink jet printing device can be combined with computer, graphical design, sample can be scaled and beat
Print is combined, and can meet the requirement of short route, small lot, multi items, even can accomplish to customize image.In particular with spray
The continuous renewal of ink-printed equipment, the improving constantly and the improvement of ink performance of dyestuff performance, ink-jet printed technology causes
The extensive concern of dyeing personage.
The coloring agent used in ink-jet ink, mainly has pigment and dyestuff two kinds.Pigment ink have technique simple,
Low cost and to advantages such as fabric non-selectivities, but due to shortcomings such as Boardy Feeling, vividness difference and fastness to rubbing are low, mainly use
In outdoor air brushing.Type of dye ink is mainly used in the stamp of fabric, and various dyestuffs all can use, and is presently mainly and knits for cotton
The reactive dye of thing and for closing the disperse dyes of fine fabric.The advantage of type of dye ink mainly has: one is bright in colour, stable
Property is good, is not easily blocked shower nozzle；Two is that dye chromatography used is complete, and the 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, has not
Alternative status.
Polyester cotton dye printing is more complicated, it is common that the dye printing to every kind of fiber respective type.Wash
Synthetic fibre fabric coloring is mainly disperse dyes, and bafta can use the colorings such as reactive dye, reducing dye, soluble vat dye.
During stamp, most cotton dye is not adsorbed by polyster fibre, and a considerable amount of disperse dyes are to cotton fiber
Staining.Therefore, in polyester cotton stamp, need fully to clean with removing staining in the disperse dyes of cotton fiber, but still
The unavoidable staining that fabric bottom surface occurs.When polyester cotton blending ratio changes, the mixture of dissimilar dyestuff is at color compatibility
Difficulty is there is also in property.Further, dissimilar dyestuff on each the color on the fiber of dye in coloured light, color depth and fastness very
Difficult consistent.Accordingly, it is capable to the cross-linking reactive disperse dyes of two kinds of fiber colourings can be overcome these problems 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
Standby.Owing to using nozzle injection, need to consider the many factors of ink, the most topmost physical and chemical performance index: grain
Footpath, viscosity, surface tension, electrical conductivity etc..
Summary of the invention
The technical problem to be solved is to provide a kind of cross-linking reactive disperse dyes compound and application thereof, should
The purpose of invention is a kind of energy of invention cross-linking reactive disperse dyes compound of stamp on polyster fibre and cotton fiber simultaneously,
And be prepared into ink-jet ink and be applied to the stamp of the blend fabric such as polyester-cotton blend, solve polyester cotton pigment printing feel
The shortcomings such as difference, washing fastness difference and mixed dye printing technology long flow path, the mutual staining of dyestuff are serious.
The one cross-linking reactive disperse dyes compound of the present invention, described 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 the cross-linking reactive disperse dyes compound of the present invention, including:
(1) preparation of coupling component: by the amino benzenes compounds containing amino, epoxychloropropane, catalyst mixing, stir molten
Solve, reaction, obtain coupling component reactant liquor；Wherein the amino benzenes compounds containing amino is 1.0 with the mol ratio of epoxychloropropane:
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 response time is 30-
36h；
(2) diazotising and coupling reaction: there is the compound of amino at sodium nitrite/hydrochloric acid or salt on phenyl ring or heterocycle
There is diazo-reaction under acid/nitrosyl sulfuric acid effect, obtain diazo-reaction liquid；Wherein in diazo-reaction, containing amino
The mol ratio of phenyl amines or heterocycle compound, sodium nitrite and hydrochloric acid is 1: 1.01～1.10: 2.5-3.0, diazotising temperature 0
～5 DEG C, the response time 1～2h；Or the mol ratio of the phenyl amines or heterocycle compound, nitrosyl sulfuric acid and sulphuric acid containing amino is
1:1.01～1.10:3.0～8.0, diazotising temperature-5～5 DEG C, the response time 4～5h；Wherein R1, R2, R3, R4, R5Ibid；
(3) above-mentioned coupling component reactant liquor is completely dissolved in acetum, under agitation, adds diazotising anti-
Answering liquid to carry out coupling reaction, reaction temperature is 5-15 DEG C, and the response time is 3-4h；After reaction completely, at 60-70 DEG C, heat 1h
After, sucking filtration, washing, dry；R in coupling reaction product7And R8At least a position introduces CH2CH(OH)CH2Cl group.
In described step (1), catalyst is benzyltriethylammoinium chloride or lithium bromide.
A kind of application of the cross-linking reactive disperse dyes compound of the present invention, it is characterised in that: described disperse dyes
Compound is applied to ink-jet ink.
Described ink-jet ink includes: cross-linking disperse dye compound, dispersant, organic solvent, surfactant, anticorrosion
Agent and defoamer.
Described ink-jet ink, by the percentage ratio 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 regulator mass content 1～5%；Preservative mass content 0.5～1%；Defoamer mass content 0.5～1%；Deionized water
For surplus.
Described dispersant be MF, 85A, NNO one or more；Organic solvent is glycerol, ethylene glycol, butanone, Isosorbide-5-Nitrae-fourth
One or more in glycol, diethylene glycol, diglycol, Diethylene Glycol, diethylene glycol monoethyl ether；Surfactant
For 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.
Described ink-jet ink is for the spray printing of the ink-jet printed fabric of polyester cotton, particularly as follows: first enter fabric
Row pretreatment, pretreated fabric carries out the most ink-jet printed at ambient temperature, and PRINTED FABRIC carries out fixation.
Described pretreatment condition be sodium carbonate be 30～40g/L, carbamide is 80～100g/L, and sodium alginate former paste consumption is
(40g sodium alginate is dissolved in 960g water and prepares former paste, 40g/L) is 8～25g/L, and pick-up is 70%, then at 104 DEG C of bars
5min is dried under part；Color fixing condition carries out decatize or bakes 10～15min under the conditions of being 130～165 DEG C.
The cross-linking reactive disperse dyes of the present invention can be applied in ink-jet ink.Concrete applying step is as follows:
The preparation of mill base:
(1), after dyestuff and dispersant 1:1 (mass ratio) are fully ground, add organic solvent, part surface activating agent and go
Each component such as ionized water, abundant sand milling, obtain a slurry.(2) a slurry high pressure homogenizer is carried out homogenizing experiment, weight
Multiple three times, obtain secondary slurry.(3) secondary slurry Microfluidizer is carried out homogenizing, in triplicate, obtain three slurries
Material, is mill base.
The preparation of ink:
(1) electrical conductivity regulator, preservative and remaining surfactant and deionized water are joined gained ink color
In slurry, it is stirred well under room temperature room temperature condition uniformly；(2) again after centrifuge certain time, upper strata slurry is taken out
Material mixture；(3) this mixture is stood two weeks ripening；(4) finished product is obtained with the membrane filtration of 250nm；(5) after detection ripening
Ink mixture indices.
In the preparation process of described mill base, cross-linking reactive disperse dyes mass content 1-15%；Dispersant mass content
1-15% for ink gross mass；Organic solvent content 15-35%；Surfactant qualities content 0.18-4%；Defoamer matter
Amount content 0.5-1%；Deionized water quality content 10-50%.At this, mass content is for accounting for ink gross mass percentage composition.
In the preparation process of described 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 described mill base, high pressure homogenize condition is: pressure is 20-80MPa；Number of times is 3 times.
In the preparation process of described mill base, microjet processing condition is: pressure is 120-300MPa；Flow is 50ml/
min；Number of times is 3 times.
In described ink preparation process, preservative mass content is the 0.5-1% of ink gross mass；Electrical conductivity regulator matter
Amount content is the 1-5% of 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 described mill base, centrifugal condition is: rotating speed is 6000-12000r/min；Time is 30-60min；
In described ink preparation process, indices is (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
It is an object of the invention to invent a kind of energy cross-linking active dispersal of stamp on polyster fibre and cotton fiber simultaneously
Dye composition, and be prepared into ink-jet ink and be applied to the stamp of the blend fabric such as polyester-cotton blend, solve polyester cotton
The shortcomings such as pigment printing feel is poor, washing fastness difference and mixed dye printing technology long flow path, the mutual staining of dyestuff are serious；
The cross-linking reactive disperse dyes chromatograph that this patent relates to is complete, can make yellow, orange, red, purple,
Blue and green ink, fastness is good simultaneously, carries out a certain proportion of compounding black that can go out high pitch black degree with blending
Dyestuff；
The ink of the present invention has good printing fluency, and is printed upon on fabric having lovely luster, sun-resistant,
The advantages such as water-fastness, fastness to rubbing is good, can be used for the ink-jet printed of textile.
Accompanying drawing explanation
Fig. 1 is Dyestuff synthesis flow chart；
Fig. 2 is the infrared spectrum of example 1 dyestuff；
Fig. 3 is the infrared spectrum of example 2 dyestuff；
Fig. 4 is the infrared spectrum of example 3 dyestuff；
Fig. 5 is the infrared spectrum of example 4 dyestuff；
Fig. 6 is the infrared spectrum of example 5 dyestuff；
Fig. 7 is the infrared spectrum of example 6 dyestuff；
Fig. 8 is the infrared spectrum of example 7 dyestuff.
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, people in the art
The present invention can be made various changes or modifications by member, and these equivalent form of values fall within the application appended claims equally and limited
Scope.
Embodiment 1
Synthesis target:
Raw material includes meta nitro aniline, epoxychloropropane, aniline, benzyltriethylammoinium chloride, hydrochloric acid, sodium nitrite etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane, 18.63g in coupling reaction still pure
Degree is aniline and the 0.36g benzyltriethylammoinium chloride of 100%, and stirring is to being completely dissolved.Rotate after keeping room temperature reaction 36h and steam
Send unnecessary epoxychloropropane, have taupe dope to generate, add the stirring of 50ml30% acetic acid stand-by to being completely dissolved.
Diazo-reaction: be sequentially added in diazo-reaction still 27.6g100% meta nitro aniline, 500ml water and
50ml36% hydrochloric acid heated and stirred is to being completely dissolved, and chuck leads to condensed water, is slowly added dropwise 47.33g30% under 0-5 DEG C and normal pressure
Sodium nitrite solution, keeps diazo-reaction 1h under 0-5 DEG C and condition of normal pressure, adds sulfamic acid and eliminates the nitrous acid of excess.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 2
Synthesis target:
Raw material includes paranitroanilinum, epoxychloropropane, 3-amino-4-methoxyacetanilide, benzyl triethyl ammonium chlorination
Ammonium, hydrochloric acid, sodium nitrite etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane in coupling reaction still, 36g purity is
The 3-amino-4-methoxyacetanilide of 100% and 0.72g benzyltriethylammoinium chloride, stirring is to being completely dissolved.Keep room temperature
After reaction 36h, rotary evaporation goes out unnecessary epoxychloropropane, has dark-grey brown viscous thing to generate, and adds the stirring of 50ml30% acetic acid
Stand-by to being completely dissolved.
Diazo-reaction: be sequentially added in diazo-reaction still 27.6g100% meta nitro aniline, 500ml water and
50ml36% hydrochloric acid heated and stirred is to being completely dissolved, and chuck leads to condensed water, is slowly added dropwise 47.33g30% under 0-5 DEG C and normal pressure
Sodium nitrite solution, keeps diazo-reaction 1h under 0-5 DEG C and condition of normal pressure, adds sulfamic acid and eliminates the nitrous acid of excess.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 3
Synthesis target:
Raw material includes 2-bromo-4,6-dinitro-aniline, epoxychloropropane, an acetanilide, benzyltriethylammoinium chloride,
Sulphuric acid and nitrosyl sulfuric acid etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane in coupling reaction still, 30g purity is
Acetanilide and 0.6g benzyltriethylammoinium chloride between 100%, stirring is to being completely dissolved.Rotate after keeping room temperature reaction 36h
Evaporate unnecessary epoxychloropropane, have taupe dope to generate, add the stirring of 50ml30% acetic acid stand-by to being completely dissolved.
Diazo-reaction: be sequentially added in diazo-reaction still 52.404g100%2-bromo-4,6-dinitro-aniline,
103.6g98% sulphuric acid stirs to being completely dissolved under the conditions of 20-30 DEG C, is slowly added dropwise the nitrosyl sulfuric acid of 63.5g40%, rises
Temperature, to 50-55 DEG C of insulation reaction 1h, adds sulfamic acid and eliminates the nitrous acid of excess.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 4
Synthesis target:
Raw material includes 2-bromo-4,6-dinitro-aniline, epoxychloropropane, 3-amino-4-methoxyacetanilide, benzyl
Triethyl ammonium chloride, sulphuric acid and nitrosyl sulfuric acid etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane in coupling reaction still, 36g purity is
The 3-amino-4-methoxyacetanilide of 100% and 0.72g benzyltriethylammoinium chloride, stirring is to being completely dissolved.Keep room temperature
After reaction 36h, rotary evaporation goes out unnecessary epoxychloropropane, has taupe dope to generate, and adds 50ml30% acetic acid and stirs extremely
It is completely dissolved stand-by.
Diazo-reaction: be sequentially added in diazo-reaction still 52.404g100%2-bromo-4,6-dinitro-aniline,
103.6g98% sulphuric acid stirs to being completely dissolved under the conditions of 20-30 DEG C, is slowly added dropwise the nitrosyl sulfuric acid of 63.5g40%, rises
Temperature, to 50-55 DEG C of insulation reaction 1h, adds sulfamic acid and eliminates the nitrous acid of excess.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 5
Synthesis target:
Raw material includes 3-amino-5-nitro benzisothiazole, epoxychloropropane, aniline, benzyltriethylammoinium chloride, sulfur
Acid, nitrosyl sulfuric acid etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane, 18.63g in coupling reaction still pure
Degree is aniline and the 0.36g benzyltriethylammoinium chloride of 100%, and stirring is to being completely dissolved.Rotate after keeping room temperature reaction 36h and steam
Send unnecessary epoxychloropropane, have taupe dope to generate, add the stirring of 50ml30% acetic acid stand-by to being completely dissolved.
Diazo-reaction: be sequentially added into 178g98% concentrated sulphuric acid in diazo-reaction still and 39g purity is the 3-of 100%
Amino-5-nitro benzisothiazole, after 3-amino-5-nitro benzisothiazole is completely dissolved, chuck leads to chilled brine ,-5
～under 0 DEG C and normal pressure, it is slowly added dropwise the nitrosyl sulfuric acid of 63.5g40%, it is slowly added dropwise the propanoic acid of 39g100% after dropping,
Keeping diazo-reaction under-5～0 DEG C and condition of normal pressure, the diazotising time is 4h, adds sulfamic acid and eliminates the nitrous of excess
Acid.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 6
Synthesis target:
Raw material include 3-amino-5-nitro benzisothiazole, epoxychloropropane, an acetanilide, benzyl triethyl ammonium chlorination,
Sulphuric acid, nitrosyl sulfuric acid etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane in coupling reaction still, 30g purity is
The aniline of 100% and 0.6g benzyltriethylammoinium chloride, stirring is to being completely dissolved.After keeping room temperature reaction 36h, rotary evaporation goes out
Unnecessary epoxychloropropane, has taupe dope to generate, and adds the stirring of 50ml30% acetic acid stand-by to being completely dissolved.
Diazo-reaction: be sequentially added into 178g98% concentrated sulphuric acid in diazo-reaction still and 39g purity is the 3-of 100%
Amino-5-nitro benzisothiazole, after 3-amino-5-nitro benzisothiazole is completely dissolved, chuck leads to chilled brine ,-5
～under 0 DEG C and normal pressure, it is slowly added dropwise the nitrosyl sulfuric acid of 63.5g40%, it is slowly added dropwise the propanoic acid of 39g100% after dropping,
Keeping diazo-reaction under-5～0 DEG C and condition of normal pressure, the diazotising time is 4h, adds sulfamic acid and eliminates the nitrous of excess
Acid.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Embodiment 7
Synthesis target:
Raw material includes 3-amino-5-nitro benzisothiazole, epoxychloropropane, 3-amino-4-methoxyacetanilide, benzyl
Base triethyl group chlorination, sulphuric acid, nitrosyl sulfuric acid etc..
The preparation of coupling component: be sequentially added into 148.56g100% epoxychloropropane in coupling reaction still, 36g purity is
The 3-amino-4-methoxyacetanilide of 100% and 0.72g benzyltriethylammoinium chloride, stirring is to being completely dissolved.Keep room temperature
After reaction 36h, rotary evaporation goes out unnecessary epoxychloropropane, has taupe dope to generate, and adds 50ml30% acetic acid and stirs extremely
It is completely dissolved stand-by.
Diazo-reaction: be sequentially added into 178g98% concentrated sulphuric acid in diazo-reaction still and 39g purity is the 3-of 100%
Amino-5-nitro benzisothiazole, after 3-amino-5-nitro benzisothiazole is completely dissolved, chuck leads to chilled brine ,-5
～under 0 DEG C and normal pressure, it is slowly added dropwise the nitrosyl sulfuric acid of 63.5g40%, it is slowly added dropwise the propanoic acid of 39g100% after dropping,
Keeping diazo-reaction under-5～0 DEG C and condition of normal pressure, the diazotising time is 4h, adds sulfamic acid and eliminates the nitrous of excess
Acid.
Coupling reaction: coupling component adds ice bath and is cooled to 0～5 DEG C, slowly drips diazol, while drip in coupling component
Edged adds substantial amounts of mixture of ice and water in coupling reaction liquid.After diazol adds, keep 10～15 DEG C of reaction 3-4h,
Diazol response situation is detected with H-acid.After completion of the reaction, sucking filtration, massive laundering, dry.
The preparation of mill base: be fully ground with 15g Dispersant MF by 15g dyestuff filter-cakes, adds 10g1,4-butanediol, 10g bis-
Diglycol ethylene, 3g surfactant paregal O and 40g deionized water are sufficiently mixed.Add 100ml1.2mm zirconium pearl to exist
Filter out zirconium pearl under conditions of 4000r/min after sand milling 6h, obtain a slurry.High pressure homogenize 3 under the conditions of pressure is 60MPa
Secondary, obtain secondary slurry.It is 50ml/min processing flow, microjet homogenizing 3 times under the conditions of 120～300MPa, obtain three times
Slurry, is mill base.
The preparation of ink: add standby anti-many D2,1g defoamer Z-8415, the 2g electrical conductivity regulator of 1g preservative in mill base
Ethylenediaminetetraacetic acid；0.02g surfactant paregal O；Surplus is deionized water quality.Fully stir under room temperature room temperature condition
Mix to uniformly, more centrifugal 30min under the conditions of 10000r/min, take out upper strata mixed solution.Mixture is stood two weeks ripe
Change, obtain finished product with the membrane filtration of 250nm.Ink mixture indices after finally detection ripening: particle diameter is 200nm；Viscosity
For 2.0mPa s；Surface tension 30mN/m；Electrical conductivity is 1000 μ s/cm.
Ink spray printing on polyester cotton: first fabric is carried out pretreatment: sodium carbonate is 35g/L, and carbamide is
80g/L, sodium alginate (40g/L) is 20g/L, and pick-up is 70%.Dry fabric under the conditions of 104 DEG C, enter at ambient temperature
Row is the most ink-jet printed, and PRINTED FABRIC carries out decatize under the conditions of 165 DEG C or bakes 12min.
Table 1: embodiment of the present invention 1-7 dyestuff performance 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 | Orange | Red | Purple | Blue | Blue | Green |
| Washing (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 |
| Wet rub (level) | 3-4 | 3-4 | 4 | 4 | 4 | 4 | 4 |
| Distillation (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 with acetone as solvent.
Claims (2)
1. a preparation method for cross-linking reactive disperse dyes compound, the most cross-linking reactive disperse dyes compound structure
Formula is:
Preparation method includes:
(1) by the amino benzenes compounds containing amino, epoxychloropropane, catalyst mixing, stirring and dissolving, reaction, coupling group is obtained
Divide reactant liquor；Wherein the amino benzenes compounds containing amino is 1.0:8 with the mol ratio of epoxychloropropane, and the consumption of catalyst is for containing
The 2% of the amino benzenes compounds quality of amino, reaction temperature is 30-50 DEG C, and the response time is 30-36h；
(2) amino benzenes compounds containing amino occurs diazotising anti-under sodium nitrite/hydrochloric acid or hydrochloric acid/nitrosyl sulfuric acid effect
Should, obtain diazo-reaction liquid；Wherein in diazo-reaction, rubbing of amino benzenes compounds, sodium nitrite and the hydrochloric acid containing amino
That ratio is 1:1.01～1.10:2.5～3.0, diazotising temperature 0～5 DEG C, response time 1～2h；Or the phenyl amines containing amino
The mol ratio of compound, nitrosyl sulfuric acid and sulphuric acid is 1:1.01～1.10:3.0～8.0, and diazotising temperature-5～5 DEG C, during reaction
Between 4～5h；
(3) above-mentioned coupling component reactant liquor is completely dissolved in acetum, under agitation, adds diazo-reaction liquid
Carrying out coupling reaction, reaction temperature is 5-15 DEG C, and the response time is 3-4h；After reaction completely, at 60-70 DEG C, after heating 1h, take out
Filter, washing, dry.
The preparation method of a kind of cross-linking reactive disperse dyes compound the most according to claim 1, it is characterised in that: institute
Stating catalyst in step (1) is benzyltriethylammoinium chloride or lithium bromide.
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| CN201510412374.9A CN105176133B (en) | 2014-08-13 | 2014-08-13 | A kind of cross-linking reactive disperse dyes compound and its preparation and application |
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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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| GB856899A (en) * | 1957-10-04 | 1960-12-21 | John Reginald Atkinson | New textile colouring process |
| GB868468A (en) * | 1958-09-04 | 1961-05-17 | Ici Ltd | New monoazo dyestuffs |
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| CH501039A (en) * | 1968-07-29 | 1970-12-31 | Sandoz Ag | Process for the preparation of basic monoazo compounds |
| CH531033A (en) * | 1969-07-08 | 1972-11-30 | Sandoz Ag | Basic monoazo dyes - of benzothiazole - azo - benzene series, for leather, acrylonitrile polymers and paper |
| KR100356768B1 (en) * | 1994-04-19 | 2003-09-02 | 니폰 가야꾸 가부시끼가이샤 | Disperse dye compositions and dyeing methods for hydrophobic fibers using them |
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| GB9826659D0 (en) * | 1998-12-03 | 1999-01-27 | Basf Ag | Disperse dye mixtures |
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