CN103709790A - Dye composition, dye, preparation methods thereof and raw material composition of dye - Google Patents
Dye composition, dye, preparation methods thereof and raw material composition of dye Download PDFInfo
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- CN103709790A CN103709790A CN201310713968.4A CN201310713968A CN103709790A CN 103709790 A CN103709790 A CN 103709790A CN 201310713968 A CN201310713968 A CN 201310713968A CN 103709790 A CN103709790 A CN 103709790A
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Abstract
The invention discloses a dye composition which contains 10-70% of an ingredient represented by a formula I shown in a drawing and 30-90% of an ingredient represented by a formula II shown in a drawing. The invention further discloses a preparation method of the dye composition, wherein the method comprises the steps: (1) in a sulfuric-acid aqueous solution, carrying out diazotization reaction on mixed arylamine and a diazotization reagent at the reaction temperature of 15-35 DEG C; (2) enabling a product, obtained after the diazotization reaction, and N-ethyl-3-cyano-4-methyl-6-hydroxy-2-pyridone to be subjected to coupling reaction at the reaction temperature of -5 to 15 DEG C. The invention further discloses a raw material composition of a dye, wherein the raw material composition contains the dye composition, auxiliaries and a wetting agent. The invention further discloses a preparation method of the dye, wherein the method comprises the step of carrying out grinding and dispersing treatment on the raw material composition of the dye. The invention further discloses the dye prepared by the preparation method of the dye. During fabric dyeing, the dye disclosed by the invention is bright in color and light and good in dispersity and has excellent dyeing depth and dyeing fastness.
Description
The application is to be dividing an application of December 20, application number in 2011 are 201110430201.1, denomination of invention is " feedstock composition of dye composite, dyestuff, its preparation method and this dyestuff " patent application the applying date.
Technical field
The present invention relates to azoic dyestuff field, be specifically related to a kind of dye composite, containing its feedstock composition of dyestuff, its preparation method and this dyestuff.
Background technology
Along with the raising of people's living standard and the enhancing of environmental consciousness, high-performance environment-friendly type dye more and more comes into one's own.Environmental protection type dye except environmentally friendly, do not affect HUMAN HEALTH, also should possess good dyeing behavior.In the printing and dyeing of polyester material, no matter be monogenetic dyestuff or combination dyestuff, bright-coloured Yellow disperse dye is all widely used.Blending black or dark dark blue combined disperse dye require yellow used or ruddiness Yellow disperse dye to have good lifting force and dye level, and there is the performances such as good washing, illumination, sublimation fastness, therefore developing corresponding Yellow disperse dye has important Practical significance.
Summary of the invention
Technical problem to be solved by this invention is the inadequate defect of lifting force, dye level and fastness in order to overcome existing Yellow disperse dye, and a kind of yellow disperse dye composition is provided, containing its feedstock composition of dyestuff, its preparation method and this dyestuff.Yellow disperse dye of the present invention coloured light when textile dyeing is bright-coloured, and dispersing property is good, and has good dye level and dyefastness.
The invention provides a kind of dye composite, its composition comprise 10%～70% suc as formula the dyestuff A shown in I and 30%～90% suc as formula the dyestuff B shown in II, percentage composition is quality percentage composition;
The weight content of described dyestuff A preferably 25%～65%, more preferably 35%～55%; The weight content of dyestuff B preferably 35%～75%, more preferably 45%～65%.By regulating the ratio of A and B, can obtain the combined disperse dye of different color light, the consumption of B increases, and the ruddiness of combination dyestuff increases.
The present invention also provides the preparation method of above-mentioned dye composite, and it comprises the following steps:, in (1) aqueous sulfuric acid, mixed aromatic diamine and diazo reagent to be carried out to diazotization reaction, and temperature of reaction is 15 ℃～35 ℃; (2) product after diazotization reaction and N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone are carried out to coupled reaction, temperature of reaction is-5 ℃～15 ℃; Described mixed aromatic diamine is the mixture of 2,4-dinitraniline and 2-nitro-4-anisidine;
Described diazotization reaction can be diazotization reaction conventional in organic field, its reaction conditions can be according to 2, the diazotization reaction condition of 4-dinitraniline is selected, as can be with reference to the diazotization reaction condition in < < dyestuff manufacturing technology > > (Song little Ping chief editor).The present invention is preferably as follows reaction conditions:
Described diazotization reaction preferably includes the following step: in aqueous sulfuric acid, temperature of reaction is at 15 ℃～35 ℃, in mixed aromatic diamine (mixture of 2,4-dinitraniline and 2-nitro-4-anisidine), drips diazo reagent, carry out diazotization reaction.The concentration of described aqueous sulfuric acid preferably 70%～98%, more preferably 85%～98%(quality percentage composition); The mass ratio of described aqueous sulfuric acid and mixed aromatic diamine (mixture of 2,4-dinitraniline and 2-nitro-4-anisidine) preferably 0.6～5, more preferably 0.8～3; Described diazo reagent is 20%～45% nitrosyl sulfuric acid preferably, more preferably 40% nitrosyl sulfuric acid, and wherein, the solvent of nitrosyl sulfuric acid is that concentration is 98% sulfuric acid, percentage composition is quality percentage composition; Described diazo reagent is to the mol ratio of mixed aromatic diamine preferably 1～1.15, and more preferably 1.02～1.05; Described 2, the mol ratio of 4-dinitraniline and 2-nitro-4-anisidine preferably 0.3～1.8, more preferably 0.5～1.2; Preferably 15 ℃～32 ℃ of the temperature of reaction of described diazotization reaction, more preferably 20 ℃～25 ℃; The process of described diazotization reaction can be monitored with TLC and LC-MS, and the reactant of generally usining disappears as the terminal of reaction.
Described coupled reaction can be the coupled reaction of azoic dyestuff field routine, its reaction conditions can be selected according to the conventional coupled reaction condition of pyridine compounds, as can be with reference to the coupled reaction condition in < < dyestuff manufacturing technology > > (Song little Ping chief editor).The present invention is preferably as follows reaction conditions:
Described coupled reaction preferably includes the following step: N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone is dissolved in to basic solution and mixes with diazotization reaction product, carry out coupled reaction, temperature of reaction is-5 ℃～15 ℃.The described solution of the preferred sodium hydroxide of basic solution is, the solution of the solution of sodium carbonate or potassium hydroxide, the more preferably solution of sodium hydroxide or the solution of sodium carbonate; The concentration of described basic solution preferably 25～50%, more preferably 30～40%, percentage composition is quality percentage composition; Alkali in described basic solution and the mol ratio of pyridone preferably 2.2～3, more preferably 2.5～2.8; Described N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone and the mol ratio of mixed aromatic diamine preferably 1～1.15, more preferably 1.02～1.05; Preferably 2 ℃～8 ℃ of the temperature of reaction of described coupled reaction; The reaction process of described coupled reaction can ooze circle method with filter paper monitors, and the coupling component of generally usining is micro-excessive in reaction end.The aftertreatment of described coupled reaction preferably includes the following step: reaction system is warming up to 65 ℃～75 ℃ insulations 2 hours, filters, and washing product to elutant pH value is 6～7.
The present invention also provides a kind of feedstock composition of dyestuff, and its composition comprises: dye composite as above, auxiliary agent and wetting agent.
Wherein, described auxiliary agent can be the conventional colour additive in this area, one or more in preferred dispersants, diffusant and tensio-active agent.Described dispersion agent preferred anionic dispersion agent.The preferred naphthalene of described anionic dispersing agents and the sulfonic acid of alkyl substituent thereof and the condenses of formaldehyde, and one or more in sulfonated lignin.One or more of the sulfonic acid of described naphthalene and alkyl substituent thereof and the preferred naphthalenesulfonate formaldehyde condensation compound of the condenses of formaldehyde (being called for short NNO), methyl naphthalene sulfonic acid salt formaldehyde condensation products (being called for short MF) and benzyl naphthalenesulfonate formaldehyde condensation compound (being called for short CNF).The preferred sodium lignosulfonate Reax83A of described sulfonated lignin and Reax85A.The ratio of described auxiliary agent and the weight of dye composite is 0.7～5:1 preferably; Described diffusant and tensio-active agent can be the conventional diffusant in this area and tensio-active agent; Described wetting agent can be the conventional wetting agent in this area, preferably water; The ratio of described wetting agent and the weight of dye composite preferably 2～12.
The feedstock composition of described dyestuff is for each composition is independent or each composition is divided into the polycomponent nested form of some groups or the mixture being simply mixed to get for each composition.
The present invention also provides a kind of preparation method of dyestuff, and it comprises the following steps: the feedstock composition of above-mentioned dyestuff to carry out grinding distribution processing.
Described grinding distribution is processed the grinding distribution processing that can be this area routine, preferably use pulverizer, more preferably with sand mill or shredder, the working method of described pulverizer, sand mill and shredder and operational condition are all selected by the working method of this area routine and operational condition; The preparation method of described dyestuff also can comprise dry, described dry the dry of this area routine, the preferably spray drying of can be.
The dyestuff that the present invention also provides the preparation method by above-mentioned dyestuff to make.Described dyestuff can liquid state, emulsifiable paste shape, powdery or granular form exist; Described dyestuff can directly apply to the dyeing of hydrophobic material fiber, also can apply with other dyestuff blendings.
Without prejudice to the field on the basis of common sense, above-mentioned each optimum condition, can arbitrary combination, obtains the preferred embodiments of the invention.
Agents useful for same of the present invention and raw material be commercially available obtaining all.
Positive progressive effect of the present invention is: dye composite of the present invention not only coloured light is adjustable, and there is the features such as coloured light is bright-coloured, depth good, dyefastness is excellent, enhancing is good, good level-dyeing property, compare and there is clear superiority aspect dye stability, sub limation fastness, dye level with single component A or B, be specially adapted to dyeing and the stamp of Polyester Fibers.
Embodiment
Mode below by embodiment further illustrates the present invention, but does not therefore limit the present invention among described scope of embodiments.The experimental technique of unreceipted actual conditions in the following example, according to ordinary method and condition, or selects according to catalogue.
In the following example, each percentage composition is quality percentage composition.
Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde): Anyang dicyclo auxiliary agent limited liability company;
Dispersion agent Reax85A(sodium lignosulfonate): real big gram of (MeadWestvaco) company of virtue dimension;
C.I. Disperse Blue-79 commodity: Town in Shanghai promise its;
C.I. Red 167 commodity: Town in Shanghai promise its.
Embodiment 1: the preparation method of dye composite
By 9.16 grams of (0.05mol) 2, after 4-dinitraniline and 8.41 grams of (0.05mol) 2-nitro-4-anisidines mix, add in 15 gram of 70% sulfuric acid (0.11mol), then at 15 ℃～25 ℃ sulphuric acid solns that slowly drip 40% nitrosyl sulfuric acid, after making diazotization reaction completely, (with TLC, detect), solution (adding 30.6 gram of 30% sodium hydroxide solution dissolves) with the quality percentage composition N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone (18.20 grams) that is 16%, in 0～10 ℃ of generation coupled reaction, control to ooze circle method detection reaction terminal.After reaction finishes, reaction system is warming up to 65 ℃～75 ℃ insulations 2 hours, filters, washing product to elutant pH value is 6～7, obtain gorgeous orange coccoid dye composite, yield is 94.2%, and the weight percentage that total content is analyzed >=98%, B component through HPLC is 49.0%.
Embodiment 2: the preparation method of dye composite
By 11.72 grams of (0.064mol) 2, after 4-dinitraniline and 6.05 grams of (0.036mol) 2-nitro-4-anisidines mix, add in 11 gram of 98% sulfuric acid (0.11mol), then at 18～22 ℃, slowly drip 45% nitrosyl sulfuric acid, after complete with HPLC detection diazotization reaction, there are coupled reactions with the solution (adding 95 gram of 25% sodium carbonate solution dissolves) of the massfraction N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone (17.80 grams) that is 12% in-5～5 ℃, to ooze circle method detection reaction terminal.After reaction finishes, reaction system is warming up to 65 ℃～75 ℃ insulations 2 hours, filters, washing product to elutant pH value is 6～7, obtain gorgeous orange coccoid dye composite, yield is 94.8%, and the weight percentage that total content is analyzed >=98%, B component through HPLC is 35.0%.
Embodiment 3: the preparation method of dye composite
By 4.39 grams of (0.024mol) 2, after 4-dinitraniline and 12.78 grams of (0.076mol) 2-nitro-4-anisidines mix, add in 85 gram of 70% sulfuric acid (0.61mol), then at 28～32 ℃, slowly drip 20% nitrosyl sulfuric acid, after complete with HPLC detection diazotization reaction, there are coupled reactions with the solution (adding 38.6 gram of 50% potassium hydroxide solution dissolves) of the massfraction N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone (20.50 grams) that is 16% in 8～15 ℃, to ooze circle method detection reaction terminal.After reaction finishes, reaction system is warming up to 65 ℃～75 ℃ insulations 2 hours, filters, washing product to elutant pH value is 6～7, obtain gorgeous orange coccoid dye composite, yield is 95.3%, and the weight percentage that total content is analyzed >=98%, B component through HPLC is 75.0%.
Embodiment 4
38 gram one of 12 grams of the dye composites of the preparation method's gained by embodiment 1,12.6 grams of Dispersant MFs, dispersion agent Reax85A5.4 gram, pure water is reinstated to sand mill and carry out grinding distribution processing, then spraying is dry.
Embodiment 5
32 gram one of 16 grams of the dye composites of the preparation method's gained by embodiment 1, dispersing agent C NF7.8 gram, dispersion agent Reax85A3.4 gram, pure water is reinstated to sand mill and carry out grinding distribution processing, then spraying is dry.
Embodiment 6
36 gram one of 3 grams of the dye composites of the preparation method's gained by embodiment 1, dispersion agent NNO10.5 gram, dispersion agent Reax83A4.5 gram, pure water is reinstated to sand mill and carry out grinding distribution processing, then spraying is dry.
Embodiment 7
By the dye composite of embodiment 1 and 2 gained, by the method described in embodiment 4, make the dyestuff that grinding distribution is good, respectively get 2.5 grams, and be dispersed in 500 ml waters, draw respectively 20 milliliters, 40 milliliters, being diluted with water to 100 milliliters (is that dyeing concentration is respectively 2%o.w.f., 4%o.w.f.), with acetic acid, adjusting dye bath pH is 4～5, being warming up to 70 ℃ puts into 5 grams of polyester fiber cloths simultaneously and dyes, in 30 minutes, by 70 ℃, be warming up to 130 ℃, be incubated 50 minutes, be cooled to 90 ℃ of following drainings and clean.Cloth specimen is put into 100 milliliters of reduction clearing liquid containing 1 grams per liter caustic soda and 3 grams per liter vat powders again and cleaned in 80 ℃, the time is 20 minutes.Adopt color measurement instrument to carry out relative intensity test to the fabric of coloured differently concentration, adopt that GB GB/T3921-2008, GB/T3920-2008, GB/T8427-2008, GB/T5718-1997 test respectively that it is water-fastness, rub resistance, colour fastness to light and sub limation fastness.Test result is in Table 1.
Comparative example 1: get 2.5 grams of formula I compounds by the preparation method of embodiment 4, make dyestuff, the performance test methods that repeats embodiment 7 carries out performance test to this dyestuff.Test result is in Table 1.
Comparative example 2: get 2.5 grams of formula II compounds by the preparation method of embodiment 4, make dyestuff, the performance test methods that repeats embodiment 7 carries out performance test to this dyestuff.Test result is in Table 1.
Table 1
The dye composites that obtain according to embodiment 1,2 and 3 are applied to after dyeing, and coloured light increases and shifts to ruddiness direction with the content of dyestuff B wherein, has certain coloured light adjustability.
Embodiment 8
The dye composite that embodiment 1 is made, by the method described in embodiment 4, make dyestuff, get 0.75 gram, 1.5 grams of C.I. Disperse Blue-79 commodity, 0.25 gram of C.I. Red 167 commodity, be dispersed in 500 ml waters, draw respectively 20 milliliters, 40 milliliters, 60 milliliters, being diluted with water to 100mL(is that dyeing concentration (o.w.f.) is respectively 2%, 4%, 6%), then dye and dye rear cleaning by method described in embodiment 7.Adopt color measurement instrument to carry out relative intensity test to the fabric of coloured differently concentration, and test dyefastness.Get each 50mL of above-mentioned dyeing residual liquid, put into respectively 2.5 grams of polyester fiber cloths and dye.Dyeing test result and raffinate dyeing situation are in Table 2.
Table 2
As shown in Table 2, by dyestuff provided by the invention and other conventional dyestuff blendings, there is good compatibleness and level-dyeing property.
Claims (6)
1. a feedstock composition for dyestuff, is characterized in that composition comprises: dye composite, auxiliary agent and wetting agent;
Described dye composite comprise 10%～70% suc as formula the dyestuff A shown in I and 30%～90% suc as formula the dyestuff B shown in II, percentage composition is quality percentage composition;
2. the feedstock composition of dyestuff as claimed in claim 1, is characterized in that: the weight content of described dyestuff A is 25%～65%; The weight content of described dyestuff B is 35%～75%.
3. the feedstock composition of dyestuff as claimed in claim 1, is characterized in that: the weight content of described dyestuff A is 35%～55%; The weight content of described dyestuff B is 45%～65%.
4. the feedstock composition of the dyestuff as described in any one in claim 1～3, is characterized in that: described auxiliary agent is one or more in dispersion agent, diffusant and tensio-active agent; Described dispersion agent is anionic dispersing agents; Described auxiliary agent is 0.7～5:1 with the ratio of the weight of dye composite; Described wetting agent is water; Described wetting agent is 2～12 with the ratio of the weight of dye composite.
5. the feedstock composition of dyestuff as claimed in claim 4, is characterized in that: described anionic dispersing agents is naphthalene and the sulfonic acid of alkyl substituent and the condenses of formaldehyde, and one or more in sulfonated lignin.
6. the feedstock composition of dyestuff as claimed in claim 5, is characterized in that: described naphthalene and the sulfonic acid of alkyl substituent thereof and the condenses of formaldehyde are one or more of naphthalenesulfonate formaldehyde condensation compound, methyl naphthalene sulfonic acid salt formaldehyde condensation products and benzyl naphthalenesulfonate formaldehyde condensation compound; Described sulfonated lignin are sodium lignosulfonate.
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| CN201310713968.4A CN103709790A (en) | 2011-12-20 | 2011-12-20 | Dye composition, dye, preparation methods thereof and raw material composition of dye |
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| CN201310713968.4A CN103709790A (en) | 2011-12-20 | 2011-12-20 | Dye composition, dye, preparation methods thereof and raw material composition of dye |
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| CN201110430201.1A Division CN103173037B (en) | 2011-12-20 | 2011-12-20 | Dye composition, dye, preparation method and raw material composition of dye thereof |
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Citations (8)
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| CN1125240A (en) * | 1995-12-20 | 1996-06-26 | 大连理工大学化工学院 | Monoazo type pyridone series compound dye |
| JP2000038522A (en) * | 1998-05-15 | 2000-02-08 | Sumitomo Chem Co Ltd | Reactive dye mixture and its application |
| CN1844261A (en) * | 2006-05-15 | 2006-10-11 | 浙江闰土股份有限公司 | Environment-friendly combined yellow disperse dye |
| CN1850913A (en) * | 2006-05-18 | 2006-10-25 | 浙江闰土股份有限公司 | Brightyellow combined dispersible dye |
| CN1916083A (en) * | 2006-08-09 | 2007-02-21 | 浙江龙盛集团股份有限公司 | Admixture of disperse dyes |
| CN101880476A (en) * | 2010-06-29 | 2010-11-10 | 浙江龙盛染料化工有限公司 | Yellow-to-orange disperse dye composition |
| CN101935465A (en) * | 2010-08-26 | 2011-01-05 | 浙江龙盛集团股份有限公司 | Disperse yellow brown dye composition |
| JP2011518895A (en) * | 2008-03-25 | 2011-06-30 | ダイスター・カラーズ・ドイッチュラント・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Azopyridone disperse dyes, their preparation and use |
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2011
- 2011-12-20 CN CN201310713968.4A patent/CN103709790A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1125240A (en) * | 1995-12-20 | 1996-06-26 | 大连理工大学化工学院 | Monoazo type pyridone series compound dye |
| JP2000038522A (en) * | 1998-05-15 | 2000-02-08 | Sumitomo Chem Co Ltd | Reactive dye mixture and its application |
| CN1844261A (en) * | 2006-05-15 | 2006-10-11 | 浙江闰土股份有限公司 | Environment-friendly combined yellow disperse dye |
| CN1850913A (en) * | 2006-05-18 | 2006-10-25 | 浙江闰土股份有限公司 | Brightyellow combined dispersible dye |
| CN1916083A (en) * | 2006-08-09 | 2007-02-21 | 浙江龙盛集团股份有限公司 | Admixture of disperse dyes |
| JP2011518895A (en) * | 2008-03-25 | 2011-06-30 | ダイスター・カラーズ・ドイッチュラント・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Azopyridone disperse dyes, their preparation and use |
| CN101880476A (en) * | 2010-06-29 | 2010-11-10 | 浙江龙盛染料化工有限公司 | Yellow-to-orange disperse dye composition |
| CN101935465A (en) * | 2010-08-26 | 2011-01-05 | 浙江龙盛集团股份有限公司 | Disperse yellow brown dye composition |
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Application publication date: 20140409 |