CN104087012B - The application of azo disperse dye goods - Google Patents
The application of azo disperse dye goods Download PDFInfo
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- CN104087012B CN104087012B CN201310566920.5A CN201310566920A CN104087012B CN 104087012 B CN104087012 B CN 104087012B CN 201310566920 A CN201310566920 A CN 201310566920A CN 104087012 B CN104087012 B CN 104087012B
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Abstract
The invention discloses the application of azo disperse dye goods in dyeing and/or the stamp of hydrophobic synthetic fibre and blend fibre material thereof; These azo disperse dye goods comprise that weight ratio is dispersant and the composition of 1～9:1; Said composition comprises: 0～30% dyestuff A, 2～45% dyestuff B, 40～47.5% dyestuff C and 15～46.25% dyestuff D; Dyestuff A is one or more in formula I compound, and dyestuff B is one or more in formula II compound, and dyestuff C is one or more in formula III compound, and dyestuff D is one or more in formula IV compound. Azo disperse dye product application of the present invention, after the dyeing and/or stamp of hydrophobic synthetic fibre and blend fibre material thereof, can be obtained to the dark blue printed article to black of dyefastness excellence.
Description
Technical field
The present invention relates to dyeing and printing and dyeing Material Field, relate in particular to a kind of azo disperse dye goodsApplication.
Background technology
Along with improving constantly that the fast development of fibrous material in recent years and people require textile, correspondingGround, dyeability, environmental-protecting performance that people have dyestuff itself are also had higher requirement, and wantAsk dyestuff to there is excellent dyeability and good environmental-protecting performance.
Azo disperse dye is synthetic relatively simple with it, easily realizes the advantages such as large-scale industrial production and accounts forAccording to the very large market share. But, the dyestuff product such as black and disperse navy blue of common dispersion from the marketKind, aspect dyefastness, especially aspect fastness to sublimation, still can not meet people's completelyRequirement.
Summary of the invention
It is black and disperse that technical problem to be solved by this invention is to have overcome on market existing dispersionThe dark blue dye species that waits, aspect dyefastness, especially not good the lacking of performance aspect fastness to sublimationFall into, a kind of azo disperse dye composition, azo disperse dye goods and preparation method thereof are providedAnd application. Azo disperse dye composition of the present invention and azo disperse dye goods are particularly useful forThe printing and dyeing of hydrophobic synthetic fibre material and blend fabric thereof. Described azo disperse dye goods haveExcellent dyeability and preferably environmental-protecting performance. Preparation method's technique of the present invention is simple, operating processEnvironmental protection, is beneficial to large-scale industrial production.
The present invention solves the problems of the technologies described above by the following technical programs.
The invention provides a kind of azo disperse dye composition, it comprises the group of following weight percentagePoint: 0～30% dyestuff A, 2～45% dyestuff B, 40～47.5% dyestuff C and 15～46.25%Dyestuff D; Wherein, dyestuff A is one or more in formula I compound, and dyestuff B is formula II chemical combinationOne or more in thing, dyestuff C is one or more in formula III compound, dyestuff D is formula IVOne or more in compound;
Described formula I compound is:
In formula I, R1For hydrogen, methyl or ethyl, R2For methylene or
Described formula II compound is:
In formula II, R3For methyl or ethyl;
Described formula III compound is:
In formula III, R4For halogen or cyano group, R5And R6Be methyl or ethyl independently respectively, R7WithR8Be hydrogen, methyl, ethyl, pi-allyl, acetyl oxygen ethyl or propionyl oxygen ethyl independently respectively;
Described formula IV compound is:
In formula IV, R9For halogen, nitro or cyano group, R10For halogen, hydrogen, nitro or cyano group, R11For methyl, ethyl or phenyl, R12And R13Be methyl or ethyl independently respectively.
In formula I, R1Be preferably hydrogen.
In formula II, R3It is preferably methyl.
In formula III, R4Being preferably halogen, is more preferably chlorine or bromine; R5And R6It is preferably methyl;R7And R8Be preferably ethyl, acetyl oxygen ethyl or pi-allyl independently respectively.
In formula IV, R9It is preferably nitro; R10Being preferably halogen, is more preferably chlorine or bromine; R11It is preferably methyl or phenyl; R12And R13It is preferably ethyl.
In a preferred embodiments of the present invention, described azo disperse dye composition, wherein,Described dyestuff A is formula I-1 compound and/or formula I-2 compound, and described formula I-1 compound is:
Described formula I-2 compound is:
Wherein, described dyestuff B is preferably formula II-1 compound, and described formula II-1 compound is:
Wherein, described dyestuff C is preferably formula III-1 compound, formula III-2 compound, formula III-3One or more in compound, formula III-4, formula III-5 compound and formula III-6 compound; Described formulaIII-1 compound is:
Described formula III-2 compound is:
Described formula III-3 compound is:
Described formula III-4 compound is:
Described formula III-5 compound is:
Described formula III-6 compound is:
Wherein, described dyestuff D is preferably formula IV-1 compound, formula IV-2 compound, formula IV-3One or more in compound and formula IV-4 compound; Described formula IV-1 compound is:
Described formula IV-2 compound is:
Described IV-3 compound is:
Described IV-4 compound is:
In the time of preparation azo disperse dye composition of the present invention, described dyestuff A, institute usedState dyestuff B, described dyestuff C and described dyestuff D and can adopt commercially available prod, or by art technologyThe method that personnel know is synthetic.
The present invention also provides a kind of azo disperse dye goods, and it comprises that weight ratio is 1～9:1'sDispersant and described azo disperse dye composition.
Wherein, described dispersant conventional dispersant or diffusant etc. while being disperse dyes blending, canTo be anion surfactant and/or non-ionic surface active agent. In the present invention, described dispersantGood the earth pertaining to YIN ion dispersant, be more preferably naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products,One or more in benzyl naphthalene sulfonic formaldehyde condensation compound and lignosulfonates. Described naphthalenesulfonateformaldehyde formaldehydeCondensation product is preferably dispersing agent NNO. Described alkyl naphthalene sulfonic acid formaldehyde condensation products is preferably for disperseingAgent MF(condensation compound of methyl naphthalene sulfonic acid and formaldehyde). Described benzyl naphthalene sulfonic formaldehyde condensation compound is preferably for dividingPowder CNF(benzyl naphthalene sulfonic formaldehyde condensation compound). Described lignosulfonates are preferably ligninSodium sulfonate. In the present invention, described dispersant is more preferably Dispersant MF, or Dispersant MF andSodium lignin sulfonate.
Dye preparations of the present invention, its color is dark blue to black.
According to this area general knowledge, can, according to the consumption of this area routine and using method, adopt of the present inventionDye preparations, the operation such as print and dye. In addition, dye preparations of the present invention also can make with this area routineWith levelling agent and auxiliary agent together use.
The present invention also provides a kind of preparation method of described azo disperse dye goods, under it comprisesState step:
The water of described azo disperse dye composition, dispersant and Ren Jia is mixed, after grinding,Obtain; Or, by the described dyestuff A in described azo disperse dye composition, described dyestuff B,Described dyestuff C and described dyestuff D grind respectively in the case of the water of dispersant and Ren Jia exists,After grinding, by all mixing of materials, to obtain final product; Wherein, the gross weight of described dispersant and described azo divideThe weight ratio of loose dye composite is 1～9:1.
By this area general knowledge, the consumption of the water adding in the steps such as described mixing, grinding can be abilityThe consumption of territory routine. The consumption of the described water preferably solid content in the slurry when making to grind is35～45%, more preferably the solid content in the slurry when making to grind is 40%.
Wherein, described dispersant conventional dispersant or diffusant etc. while being disperse dyes blending, canTo be anion surfactant and/or non-ionic surface active agent. In the present invention, described dispersantGood the earth pertaining to YIN ion dispersant, be more preferably naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products,One or more in benzyl naphthalene sulfonic formaldehyde condensation compound and lignosulfonates. Described naphthalenesulfonateformaldehyde formaldehydeCondensation product is preferably dispersing agent NNO. Described alkyl naphthalene sulfonic acid formaldehyde condensation products is preferably for disperseingAgent MF(condensation compound of methyl naphthalene sulfonic acid and formaldehyde). Described benzyl naphthalene sulfonic formaldehyde condensation compound is preferably for dividingPowder CNF(benzyl naphthalene sulfonic formaldehyde condensation compound). Described lignosulfonates are preferably ligninSodium sulfonate. In the present invention, described dispersant is more preferably Dispersant MF, or Dispersant MF andSodium lignin sulfonate.
Wherein, the method for described grinding and condition can be method and the condition of this area routine. Described grindingAfter grain diameter be preferably 0.1～10 micron, be more preferably 0.8～1.2 micron. Described grinding canFor ball mill ball milling, sand mill sand milling or vibrations mill etc.
Wherein, before described grinding, preferably also carry out the heat treated step of material. Described material heatThe temperature of processing is preferably 30～98 DEG C, is more preferably 40～80 DEG C, is 50～70 DEG C best. ?After described material heat treatment, should carry out immediately follow-up grinding operation, separation process in the middle of avoiding. IfIn the time of described material heat treatment, described dispersant does not all add and mixes, so remaining pointPowder should all add before the grinding described in carrying out. Conventionally, in the time of described material heat treatment,Add 20～50% the described dispersant with described azo disperse dye composition weight meter, goodlyAdd 25～50% the described dispersant with described azo disperse dye composition weight meter goodly.
By this area general knowledge, after described milled processed, can select to be dried processing, to removeMoisture. The method of described dry processing and condition can be method and the condition of this area routine. Described dryProcessing is preferably spray drying treatment. The condition of described spray drying treatment is preferably: air inlet temperatureSpend 110～150 DEG C, preferably 120～140 DEG C, more preferably 130～135 DEG C; 50～80 DEG C of air outlet temperature,Preferably 60～75 DEG C. By this area general knowledge, be dried after processing, the azo obtaining disperses to dyeMaterial products is solid.
Azo disperse dye goods described in the present invention also provides are at hydrophobic synthetic fibre and mixedSpin the application in dyeing and/or the stamp of fibrous material.
Wherein, described hydrophobic synthetic fibre material can be the hydrophobic synthetic fibre material of this area routineMaterial, is preferably polyester fiber (PETG) or Fypro (nylon),It is more preferably polyester fiber.
Wherein, described blend fibre material can be those hydrophobic synthetic fibres conventional in this areaBlend fibre material, be preferably polyester fiber blend fibre material, as polyester/cotton blend fibre material,Polyester/wool blend fibre material etc. Can there is shape for the routine of this area in described blend fibre materialFormula, as fiber, yarn, woven fabric, knitted fabric or non-woven fabric.
By azo disperse dye product application of the present invention in hydrophobic synthetic fibre and blend fibre thereofAfter the dyeing and/or stamp of material, can obtain the dark blue printed article to black of dyefastness excellence.
Meeting on the basis of this area general knowledge, above-mentioned each optimum condition, can be combined, i.e. get Ben FaBright each preferred embodiments.
Agents useful for same of the present invention and raw material be commercially available obtaining all.
Positive progressive effect of the present invention is:
Azo disperse dye composition of the present invention and azo disperse dye goods are particularly useful for dredgingThe printing and dyeing of water-based composite fibre materials and blend fabric thereof. Azo disperse dye goods of the present invention are for hidingCyan is to black, and it has excellent dyeability and good environmental-protecting performance. Preparation method of the present inventionTechnique is simple, and operating process environmental protection, is beneficial to large-scale industrial production.
Detailed description of the invention
Mode below by embodiment further illustrates the present invention, but does not therefore limit the present invention toAmong described scope of embodiments. The experimental technique of unreceipted actual conditions in the following example, according to oftenRule method and condition, or select according to catalogue.
Embodiment 1
A kind of azo disperse dye composition, it comprises: 25.1 grams of formula I-1 compounds, 24.8 grams of formulasI-2 compound, 25.6 grams of formula II-1 compounds, 68 grams of formula III-1 compounds, 8.2 grams of formula IV-1 chemical combinationThing, 8.7 grams of formula IV-3 compounds and 8.6 grams of formula IV-4 compounds.
A preparation method for azo disperse dye goods, it comprises the steps:
By above-mentioned azo disperse dye composition, 163 grams of Dispersant MF (methyl naphthalene sulfonic acid and formaldehyde contractingsCompound) and 41 grams of sodium lignin sulfonates mixing, add 560 ml waters, then in sand mill, grind togetherGrind 3～5 hours, after grinding, the particle diameter of particle, at 0.1～10 micron, is then sprayed and is dried (air intake130～135 DEG C, mouth, 60～75 DEG C of air outlets), obtain about 300g azo disperse dye goods.
Embodiment 2
A kind of azo disperse dye composition, it comprises: 38.1 grams of formula I-2 compounds, 38.4 grams of formulasII-1 compound, 68 grams of formula III-2 compounds, 12.5 grams of formula IV-1 compounds and 13 grams of formula IV-3izationCompound.
A preparation method for azo disperse dye goods, it comprises the steps:
(1) by 38.1 grams of formula I-2 compounds, 36.58 grams of Dispersant MFs and 9.14 grams of lignin sulfonic acidsSodium mixes, and adds 125.7 ml waters, is heated to 50 DEG C and carries out material heat treatment, then grind,After grinding, the particle diameter of particle is at 0.5～1.2 micron;
(2) by 38.4 grams of formula II-1 compounds, 36.86 grams of Dispersant MFs and 9.22 grams of sulfomethylated ligninsAcid sodium mixes, and adds 126.7 ml waters, is heated to 70 DEG C and carries out material heat treatment, then grind,After grinding, the particle diameter of particle is at 0.1～5 micron;
(3) by 68 grams of formula III-2 compounds, 65.28 grams of Dispersant MFs and 16.32 grams of sulfomethylated ligninsAcid sodium mixes, and adds 224.4 ml waters, is heated to 98 DEG C and carries out material heat treatment, then grind,After grinding, the particle diameter of particle is at 4～10 microns;
(4) by mixed to 12.5 grams of formula IV-1 compounds, 12 grams of Dispersant MFs and 3 grams of sodium lignin sulfonatesClose, add 41.3 ml waters to grind, after grinding, the particle diameter of particle is at 0.5～6 micron;
(5) by 13 grams of formula IV-3 compounds, 12.48 grams of Dispersant MFs and 3.12 grams of lignin sulfonic acidsSodium mixes, and adds 42.9 ml waters to grind, and after grinding, the particle diameter of particle is at 0.8～1.2 micron;
(6) by even the mixing of materials obtaining after grinding in above-mentioned steps (1)～(5), then carry outSpraying dry (130～135 DEG C of air inlets, 60～75 DEG C of air outlets), obtains about 300g azo and dispersesDye preparations.
Embodiment 3～16
Azo disperse dye composition as shown in table 1, dispersant and water are mixed, according to enforcementThe preparation method of example 1 prepares azo disperse dye goods. In table 1, I-1 compound is abbreviated as I-1,All the other compounds all by that analogy.
Comparative example 1～2
Preparation method is with embodiment 3～16.
Table 1
In above-described embodiment 1～2, prepared azo disperse dye goods are solid. Above-mentioned enforcementIn example 3～16 and comparative example 1～2, prepared azo disperse dye goods are solid.
Effect embodiment 1
5 grams, azo disperse dye goods getting embodiment 1, are dispersed in 500 ml waters, draw 20After milliliter, mix with the water of 80 milliliters, with vinegar acid for adjusting pH value to 4～5, be warming up to 70 DEG C, put into 5Gram polyester fiber cloth dyes, and in 30 minutes, is warming up to 130 DEG C by 70 DEG C, is incubated 50 minutes,Be cooled to below 90 DEG C, draining is cleaned. Again cloth specimen is put into and contained 1 grams per liter caustic soda and 3g/L sodium hydrosulfite100 milliliters of reduction cleaning liquid in, at 80 DEG C, clean, scavenging period is 20 minutes. DryAfter black dyeing.
According to above-mentioned colouring method, get respectively 5 grams of embodiment 3～16 and comparative example's 1～2 idolNitrogen type disperse dye goods, dye to polyester fiber cloth, and gained dyeing color sees the above table 1.
Effect embodiment 2
According to the colouring method of effect embodiment 1, by the azo disperse dye goods of embodiment 1～16To the blend fabric such as polyester/cotton, polyester/wool, and Fypro dyes. Gained dyeingOr polyster fibre color sees the following form shown in 2. Wherein, polyester/cotton fiber cloth is on market common 60/40Polyester cotton, polyester/wool fiber cloth is common 70/30 to wash wool blended textile fabric on market.
Table 2
Effect embodiment 3
According to GB GB/T3921-2008, GB/T3920-2008, GB/T3922-1995,The method of testing of GB/T8426-1998 and GB/T5718-1997 is the azo of test implementation example 1～16 respectivelyThe performance of the dyeing that type disperse dye goods and comparative example's 1～2 dye preparations dyes, its surveyTest result is as shown in table 3 below. Wherein, the azo disperse dye goods of embodiments of the invention 1～16Fastness to washing be 4 grades, fastness to rubbing is 4 grades, fastness to perspiration is more than 4 grades, sun-resistant jailDegree is 4～5 grades, and color fastness to sublimation is 4～5 grades.
Table 3
| Numbering | Fastness to washing | Fastness to rubbing | Fastness to perspiration | Sunlight fastness | Fastness to sublimation |
| Embodiment 1～16 | 4 | 4 | 4 | 4～5 | 4～5 |
| Comparative example 1 | 3～4 | 4 | 4 | 4 | 3～4 |
| Comparative example 2 | 3～4 | 4 | 4 | 4 | 3～4 |
Can be found out by table 3 contrast, the dyeability of the azo disperse dye goods of embodiment 1～16,Especially fastness to sublimation is better than the dyeability of comparative example 1～2 dye preparations.
Remarks: in GB, 4～5 grades of expressions are better than 4 grades, are worse than 5 grades; 3～4 grades of expressions are than 3 gradesGood, be worse than 4 grades.
Claims (10)
1. azo disperse dye goods dying at hydrophobic synthetic fibre and blend fibre material thereofApplication in look and/or stamp;
These azo disperse dye goods, it comprises that weight ratio is that dispersant and the azo of 1～9:1 dividesLoose dye composite; Described azo disperse dye composition is by the component group of following weight percentageBecome: 0～30% dyestuff A, 2～45% dyestuff B, 40～47.5% dyestuff C and 15～46.25%Dyestuff D; Wherein, dyestuff A is one or more in formula I compound, and dyestuff B is formula II chemical combinationOne or more in thing, dyestuff C is one or more in formula III compound, dyestuff D is formula IVOne or more in compound;
Described formula I compound is:
In formula I, R1For hydrogen, methyl or ethyl, R2For methylene or
Described formula II compound is:
In formula II, R3For methyl or ethyl;
Described formula III compound is:
In formula III, R4For halogen or cyano group, R5And R6Be methyl or ethyl independently respectively, R7WithR8Be methyl, ethyl, pi-allyl, acetyl oxygen ethyl or propionyl oxygen ethyl independently respectively;
Described formula IV compound is:
In formula IV, R9For halogen, nitro or cyano group, R10For halogen, hydrogen, nitro or cyano group, R11For methyl, ethyl or phenyl, R12And R13Be methyl or ethyl independently respectively.
2. application as claimed in claim 1, is characterized in that, in formula I, and R1For hydrogen; And/or,In formula II, R3For methyl; And/or, in formula III, R4For halogen; R5And R6For methyl; R7WithR8Be ethyl, acetyl oxygen ethyl or pi-allyl independently respectively; And/or, in formula IV, R9For nitro;R10For halogen; R11For methyl or phenyl; R12And R13For ethyl.
3. application as claimed in claim 2, is characterized in that, in formula III, and R4For chlorine or bromine; With/ or, in formula IV, R10For chlorine or bromine.
4. application as claimed in claim 1, is characterized in that, described dyestuff A is formula I-1izationCompound and/or formula I-2 compound, described formula I-1 compound is:
Described formula I-2 compound is:
Described dyestuff B is formula II-1 compound, and described formula II-1 compound is:
Described dyestuff C be formula III-1 compound, formula III-2 compound, formula III-3 compound, formula III-4,One or more in formula III-5 compound and formula III-6 compound; Described formula III-1 compound is:
Described formula III-2 compound is:
Described formula III-3 compound is:
Described formula III-4 compound is:
Described formula III-5 compound is:
Described formula III-6 compound is:
Described dyestuff D is formula IV-1 compound, formula IV-2 compound, formula IV-3 compound and formula IV-4One or more in compound; Described formula IV-1 compound is:
Described formula IV-2 compound is:
Described IV-3 compound is:
Described IV-4 compound is:
5. application as claimed in claim 1, is characterized in that, described dispersant is that anion dividesPowder.
6. application as claimed in claim 5, is characterized in that, described dispersant is naphthalene sulfonic acids firstAldehyde condensate, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound and lignosulfonatesIn one or more.
7. application as claimed in claim 6, is characterized in that, described naphthalene sulfonic acid-formaldehyde condensation productFor dispersing agent NNO; Described alkyl naphthalene sulfonic acid formaldehyde condensation products is Dispersant MF; Described benzyl naphthaleneSulfonic formaldehyde condensation compound is dispersing agent C NF; Described lignosulfonates are sodium lignin sulfonate.
8. application as claimed in claim 7, is characterized in that, described dispersant is Dispersant MF,Or Dispersant MF and sodium lignin sulfonate.
9. the application as described in claim 1～8 any one, is characterized in that, described hydrophobicity is closedBecoming fibrous material is polyester fiber or Fypro; Described blend fibre material is polyester fiber blendingFibrous material.
10. application as claimed in claim 9, is characterized in that, described hydrophobic synthetic fibre materialMaterial is polyester fiber; Described blend fibre material is that polyester/cotton blend fibre material or polyester/wool are mixedSpin fibrous material.
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| CN105131648A (en) * | 2015-07-03 | 2015-12-09 | 浙江亿得化工有限公司 | Novel composite black disperse dye |
| CN106833019B (en) * | 2016-12-31 | 2019-06-18 | 浙江龙盛化工研究有限公司 | A kind of high fastness indigo plant is to black disperse dye composition and dye preparations |
| CN106893360B (en) * | 2017-03-10 | 2019-04-02 | 安徽新生纺织有限公司 | A kind of admixture of disperse dyes |
| CN107345083B (en) * | 2017-06-28 | 2019-08-13 | 浙江龙盛化工研究有限公司 | It is a kind of blue to black disperse dye composition and dye preparations |
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| CN102061106A (en) * | 2010-12-08 | 2011-05-18 | 浙江吉华集团有限公司 | Azo disperse dye mixture and dye product thereof |
| CN102516812A (en) * | 2011-11-14 | 2012-06-27 | 浙江闰土股份有限公司 | Complex blue dye composition, complex dispersion blue dye and preparation method thereof |
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| CN102061106A (en) * | 2010-12-08 | 2011-05-18 | 浙江吉华集团有限公司 | Azo disperse dye mixture and dye product thereof |
| CN102516812A (en) * | 2011-11-14 | 2012-06-27 | 浙江闰土股份有限公司 | Complex blue dye composition, complex dispersion blue dye and preparation method thereof |
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