CN102161833A - Red temporary water-soluble disperse dye and manufacturing method and use thereof - Google Patents
Red temporary water-soluble disperse dye and manufacturing method and use thereof Download PDFInfo
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- CN102161833A CN102161833A CN2011100584894A CN201110058489A CN102161833A CN 102161833 A CN102161833 A CN 102161833A CN 2011100584894 A CN2011100584894 A CN 2011100584894A CN 201110058489 A CN201110058489 A CN 201110058489A CN 102161833 A CN102161833 A CN 102161833A
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Abstract
The invention discloses a red temporary water-soluble disperse dye and a manufacturing method and use thereof. The structure formula of the dye is shown below. The chromatographic peak of the dye disclosed by the invention is wide, the dyeing exhaust property of the dye is better, the raffinate is almost colorless, the molar extinction coefficient of the dye is high, and the color of the dye is bright; the yield of the dye is close to a theoretical value, and waste water treatment is convenient; and color fastness to light and color fastness to washing are greatly improved than before. The dye can be used for preparing ink for ink-jet printers. When the ink is used, the dye separated out on printing paper does not dissolve again, nor disperse upon contact with water, and thus, the application range of the ink-jet printers is expanded.
Description
Technical field
The present invention relates to a kind of dyestuff technology, particularly a kind of red temporarily water-soluble disperse dye and method for making and application.
Background technology
The fuel of Xiao Shouing all is oil-soluble colourant mostly in the market.Temporarily water-soluble disperse dye is mainly used in the dyeing and the stamp of polyster fibre.When using, can save common dispersed dye sand milling postprocessing working procedures and dispersion agent, save the energy, raise labour productivity, and can and the reactive dyestuffs mixing wash/cotton one-bath process, use very convenient.Such dyestuff is through studying over 20 years, and its chromatogram is abundanter, and still, existing in the market kind can't satisfy actual needs, particularly can not satisfy the more requirement of aspect such as multi-color kind, higher dyeing efficient.
Application number is that 95110173 Chinese patent has been introduced a kind of temporary soluble blue dispersed dye.2-chloromethyl-4-oil of mirbane alkyl ether and Thiovanic acid are carried out condensation, again through sulfide oxidation, nitroreduction, aryl amination and take off sulphur reaction etc., obtain product, its synthetic method is convenient, yield is high, the ammonium salt of product or sodium salt good water solubility, dye trevira on can be under typical conditions, and degree of fixation is preferably arranged.Application number is that 96115131.5 Chinese patent has introduced 2,6-dibromo-4-carboxysulfonateacylaminobenzene aminobenzene and synthetic method thereof.With the reaction that under acid catalysis, is hydrolyzed of 4-carboxymethyl sulfonyl Acetanilide, do not need isolate reactant, carry out bromination reaction with bromizating agent bromo-hydrogen peroxide or Hydrogen bromide-hydrogen peroxide again, obtain resultant.Through separation, washing, drying, product yield can reach 91～98%.But all also there are some defectives in these dyestuffs aspect economy, the practicality.
Application number is that 00131553.6 Chinese patent has been introduced the temporarily water-soluble azo dispersion dyes that a class contains carboxymethyl sulfonyl; it is by the diazo component that contains carboxymethyl sulfonyl and anils or pyridinone coupling; made light yellow, yellow, orange, red, purple, blue series dyes; particularly adopted diazotization-coupling one-step synthesis, the dyestuff molar extinction coefficient ε that obtains
MaxThan the similar dyestuff height of anthraquinone type, in diazo component, introduce the performance that halogen atom and cyano group have reduction carboxymethyl sulfonyl decarboxylation temperature, and can improve the maximum absorption wavelength λ of dyestuff
MaxAnd molar extinction coefficient, favourable expansion spectral range improves economy, practicality.But the dye species that this patent provides can not satisfy the actual demand in market, and a lot of kinds are still waiting to improve at aspects such as dyeing efficient, production costs, and assortment are also abundant inadequately.
Particularly red the orchil of different characteristics wavelength all has its purposes as a kind of widely used color, and present kind does not also satisfy the needs of actual use.
Summary of the invention
Technical problem to be solved by this invention provides a kind of red temporarily water-soluble disperse dye and method for making and application, thereby can increase the kind of temporarily water-soluble disperse dye, remedy similar in the past dyeing and exhaust metachromia, and the red coloured light of its dyestuff is very good, approximate bright red, remedy the insufficient shortcoming of the red coloured light of similar dyestuff, satisfy the demand in market.
For the purpose that realizes solving the problems of the technologies described above, the present invention has adopted following technical scheme:
A kind of red temporarily water-soluble disperse dye of the present invention is characterised in that its structural formula is:
A kind of red temporarily water-soluble disperse dye of the present invention, its synthesis material includes diazo component, sodium hydroxide, Sodium Nitrite, coupling component, hydrochloric acid, and wherein diazo component is a 2-bromine 4-carboxysulfonateacylaminobenzene aminobenzene, and its structure is:
The coupling component is m-acetamino N, N dipropyl aniline, and its structure is:
Composition principle is:
The preparation method is:
Add entry, 2-bromine 4-carboxysulfonateacylaminobenzene aminobenzene, sodium hydroxide and Sodium Nitrite successively at the diazo component dissolving pan, addition amount of sodium hydroxide should make pH=7 ~ 7.5 of solution, treat promptly to obtain diazo component liquid after the dissolving of 2-bromine 4-carboxysulfonateacylaminobenzene aminobenzene, diazo component liquid is delivered to diazonium liquid header tank; In the coupling component dissolving pan, add entry, m-acetamino N successively, N dipropyl aniline, hydrochloric acid, the add-on of hydrochloric acid is contained HCl and m-acetamino N, N dipropyl aniline mol ratio 1:(1.05 ~ 1.25), treat m-acetamino N, obtain coupling component liquid after the dissolving of N dipropyl aniline, coupling component liquid is delivered to the coupled reaction still; Other gets in HCl is 1:(0.9 ~ 1.1 with the diazo component mol ratio) hydrochloric acid and the dilution be dilute hydrochloric acid, be delivered to the dilute hydrochloric acid header tank; Diazo component liquid and dilute hydrochloric acid are added drop-wise in the coupled reaction still by total add-on equal proportion, keep temperature of reaction in-10 ~ 2 ℃, on one side diazotization coupling on one side; The dropping time is 1 ~ 2 hour, is stirred to diazonium salt and coupling component all disappears, and after the reaction detection terminal point coupling, continues reaction and promptly obtaining the red 29# dispersion liquid of temporarily water-soluble in 2 ~ 3 hours, after neutralization, transfer intensity and stdn to obtain standard finished products.
The concentration of described dilute hydrochloric acid can be 8 ~ 25%.
Described neutralization, accent intensity and stdn, its concrete method is: the red 29# temporarily water-soluble dispersion liquid that obtains, filtering separation obtains red 29# filter cake, behind the salt acid rinsing with pH=2 ~ 4, finally obtain the highly purified standardized filter cake for the treatment of, will add deionized water in the filter cake then, be as the criterion stirring, making beating slowly drips mass concentration 10% ~ 15% ammoniacal liquor afterwards and makes it dissolving, adds the aqueous water soluble disperse dyes that water is made into massfraction about 3 ~ 5% after the dissolving fully.
Further, described diazo component, coupling component, its amount of substance ratio of Sodium Nitrite are: diazo component: coupling component: Sodium Nitrite=1:(1 ~ 1.05): 1.
Further, the determination methods that diazonium salt and coupling component all disappear is: whether excessive, whether detect coupling component with the p-Nitroaniline diazonium salt excessive if one, can detect diazo component with H acid, finishes the raw material coupling of regulation; Two, also can the chromatographically matching result.
Various concentration and content in this patent if no special instructions, all are meant mass concentration and content.
Red temporarily water-soluble disperse dye of the present invention can be used in the preparation ink for ink-jet printer.Concrete application method can be directly to use aqueous water soluble disperse dyes after the stdn as ink for ink-jet printer, also can further add stablizer, tensio-active agent, dispersion agent in the aqueous water soluble disperse dyes after stdn, then as ink for ink-jet printer.Containing red temporarily water-soluble disperse dye mass content in the preferred ink for ink-jet printer is 0.2 ~ 5% of ink total mass.
Further, described stablizer is for being ammoniacal liquor, and tensio-active agent is glycol dimethyl ether, ethylene glycol, and dispersion agent is JFC.This JFC is meant dispersion agent commonly used in the textile industry or is permeate agent, wetting agent, is the condenses of oxyethane and high fatty alcohol.
Further, described stabilizing agent dosage is 0.5% of an ink total mass, and dosage of surfactant is 1% of an ink total mass, and dispersant dosage is 0.1% of an ink total mass.
Common dyestuff is in order to the preparation ink for ink-jet printer, oil-soluble in water dispersion effect not good, often need a large amount of stablizer of mechanical disintegration, grinding, adding, tensio-active agent etc., and be easy to generate precipitation, cohesion etc.; Water miscible dyestuff is then met the water capacity and is easily produced dipping.Thereby manufacturing process is loaded down with trivial details, the manufacturing cost height, length consuming time, power consumption is many, the dye granule diameter is required high, in the time of must reaching enough thin, not so easy blocking sprayer; Inorganic salt content can not be high, and dyestuff is unfavorable for applying with before needing desalination to purify; The dyestuff of this patent does not need to grind, disperse, and stdn can directly be used later, and manufacturing process is simple, and water-soluble back adds auxiliary agent and gets final product, and requirement condition is not high, does not need making beating to grind; There is not the dye granule problem, is always dissolved state, just do not have the problem of blocking sprayer yet; Inorganic salt content does not seldom need desalination to purify again; And the ink for ink-jet printer of preparation, after separating out dyestuff on the printer paper, dyestuff can secondary dissolving, can be not water stain, water droplet and produce the ink marks diffusion phenomena because of having on the paper, thus expanded the range of application of ink-jet printer.
By adopting technique scheme, the present invention has following beneficial effect:
A kind of red temporarily water-soluble disperse dye of this patent, its chromatographic peak width, maximum absorption wave reaches 502nm, can be used as the dyeing and the stamp of ordinary polyester and ultra-fine polyester fiber, it is better that its dyeing exhausts metachromia, and raffinate is shallow to closely colourless, higher than existing dyestuff molar extinction coefficient, color is more bright-coloured; Be particularly useful for colorant match and coloured light is gorgeous.Because it is water miscible before application, bring great convenience for the preparation of printing paste and staining fluid; Do not contain dispersion agent and levelling agent in the dyestuff, wastewater treatment is convenient, helps waste water recycling.Can not produce color spot, color dot during dyeing, printing paste is transparent, and printed pattern is meticulous; On ultra-fine polyester fiber, also can obtain uniform color and luster without levelling agent, it is good that dyeing exhausts metachromia.Use in the preparation ink for ink-jet printer, the ink for ink-jet printer of preparation is compared with common ink for ink-jet printer, has the special technique effect.Common ink for ink-jet printer, after printing to paper, still have water-soluble, in case water stain, water droplet is arranged on the paper, then since dye soluble separate in water, ink marks will spread.The ink for ink-jet printer of the red temporarily water-soluble disperse dye preparation of this patent, after separating out dyestuff on the printer paper, dyestuff can the secondary dissolving, can be not water stain because of having on the paper, water droplet and produce the ink marks diffusion phenomena.So just protected the technique effect of printing effectively, printer paper can also can be applied under particular requirement.
It is with general the different of dispersed dye:
1) it does not need sand milling, need not add dispersion agent, cohere can not take place, and can not be subjected to the interference of dispersion agent when dyeing yet;
2) because its neutral sodium-salt or ammonium salt water soluble can directly be made aqueous or the paste form, do not need spraying drying;
3) the temporary soluble disperse dye of this patent is that structural form with molecule inner salt exists under solutions of weak acidity; Filtrate very slight color when therefore filtering or colourless, building-up reactions yield be near theoretical amount, in the water contained organism seldom, waste water treatment is comparatively convenient, helps recovery of Waste Water.
Products production flow process weak point of the present invention, energy-saving and environmental protection, Sustainable development; Its great advantage is that crest is very wide, satisfies similar dye colour deficiency, can not better risk the problem of black, and its Exposure to Sunlight washing fastness all improved a lot more in the past in addition.
Description of drawings
Fig. 1 is the red temporarily water-soluble disperse dye synthetic method route map of this patent.
Embodiment
Embodiment 1
The diazo component dissolving pan adds the 2-bromo-4-carboxysulfonateacylaminobenzene aminobenzene 75.11g of entry 190g, purity 97.5% successively, the sodium hydroxide neutralization of purity 96% is dissolved into molten entirely, addition amount of sodium hydroxide makes pH=7 ~ 7.5 of solution, the Sodium Nitrite 58.51ml that adds concentration 29.48g/100ml then, on the rocksly be cooled to 0 ~ 1 ℃, promptly obtain diazo component liquid, diazo component liquid is delivered to diazonium liquid header tank; The m-acetamino N that in the coupling component dissolving pan, adds entry 125g, purity 99% successively, the hydrochloric acid 25ml of N dipropyl aniline 58.92g, concentration 36.5%, treat m-acetamino N, obtain coupling component liquid after the dissolving of N dipropyl aniline, coupling component liquid is delivered to the coupled reaction still; Other gets a part of 36.5% hydrochloric acid 20.3ml dilution is 20% and is delivered to the dilute hydrochloric acid header tank; To join in the coupled reaction still by total add-on equal proportion through diazo component liquid and the dilute hydrochloric acid after the header tank metering, keep temperature of reaction below 0 ℃, on one side diazotization coupling on one side; Dripped about 2 ~ 3 hours, and be stirred to diazonium salt and coupling component all disappears, after the reaction detection terminal point coupling, continue reaction and promptly obtaining the temporarily water-soluble Disperse Red 29# aqueous solution in 2 ~ 3 hours, after neutralization, transfer intensity and stdn to obtain standard finished products.
The maximum absorption wavelength λ of products obtained therefrom
MaxBe 502nm.
The concrete technological measure of stdn is: highly purifiedly treat in the standardized filter cake to add a little deionized water to what obtain behind the acid rinsing, be as the criterion stirring, making beating slowly drips 10% ammoniacal liquor afterwards and makes it dissolving, adds the aqueous water soluble disperse dyes that water is made into massfraction 3% after the dissolving fully.
Embodiment 2
3% the aqueous water soluble disperse dyes of using embodiment 1 preparation is as ink for ink-jet printer, and after the printing, writing is even, and after separating out dyestuff on the printer paper, dyestuff can the secondary dissolving.On the paper after the printing, drip water droplet, do not produce the ink marks diffusion.
Embodiment 3
Use 3% aqueous water soluble disperse dyes of embodiment 1 preparation, 0.5% the ammoniacal liquor that adds the ink total mass, the glycol dimethyl ether of ink total mass 1%, the JFC dispersion agent of ink total mass 0.1% is after mixing, as ink for ink-jet printer, after the printing, writing is even, and after separating out dyestuff on the printer paper, dyestuff can the secondary dissolving.On the paper after the printing, drip water droplet, do not produce the ink marks diffusion.
Comparative Examples
According to the described method of patent CN1289803A, prepare described red-23, red-10 dispersed dye of CN1289803A, carry out performance comparison with the red 29# dispersed dye of patent preparation, the gained result is as shown in table 1 below:
Table 1 dispersed dye red-29 and red-23, red 10 performance comparison results
Remarks: printing and dyeing efficient is meant the identical woven dacron length of using 100g dye capable of dyeing look.
Firmness is meant the Exposure to Sunlight washing fastness, is carrying out using under the soap boiling 15min condition result of light fastness tester according to standard GB/T 413-1978 dyeing cloth light fastness determination of test method with 80 ℃ under the 3g/L concentration after the dyeing.
From above table as can be seen, red-29 dispersed dye that this patent is prepared, compare with the prior art dyestuff, have the molar extinction coefficient height, up to 60000-70000, and solvability is good, go for the dyeing and the stamp of ultra-fine polyester fiber, dyeing coloured light is gorgeous, and raffinate is intimate colourless behind the high-temperature pressure dyeing, feature performance benefits such as degree of exhaustion height.
Claims (6)
1. red temporarily water-soluble disperse dye, feature is that its structural formula is:
The preparation method of the described red temporarily water-soluble disperse dye of a kind of claim 1, it is characterized in that: add entry, 2-bromine 4-carboxysulfonateacylaminobenzene aminobenzene, sodium hydroxide and Sodium Nitrite successively at the diazo component dissolving pan, addition amount of sodium hydroxide should make pH=7 ~ 7.5 of solution, treat promptly to obtain diazo component liquid after the dissolving of 2-bromine 4-carboxysulfonateacylaminobenzene aminobenzene, diazo component liquid is delivered to diazonium liquid header tank; In the coupling component dissolving pan, add entry, m-acetamino N successively, N dipropyl aniline, hydrochloric acid, the add-on of hydrochloric acid is contained HCl and m-acetamino N, N dipropyl aniline mol ratio 1:(1.05 ~ 1.25), treat m-acetamino N, obtain coupling component liquid after the dissolving of N dipropyl aniline, coupling component liquid is delivered to the coupled reaction still; Other gets in HCl is 1:(0.9 ~ 1.1 with the diazo component mol ratio) hydrochloric acid and the dilution be dilute hydrochloric acid, be delivered to the dilute hydrochloric acid header tank; Diazo component liquid and dilute hydrochloric acid are added drop-wise in the coupled reaction still by total add-on equal proportion, keep temperature of reaction in-10 ~ 2 ℃, on one side diazotization coupling on one side; The dropping time is 1 ~ 2 hour, is stirred to diazonium salt and coupling component all disappears, and after the reaction detection terminal point coupling, continues reaction and promptly obtaining the temporarily water-soluble dispersion liquid in 2 ~ 3 hours, after neutralization, transfer intensity and stdn to obtain standard finished products.
2. according to the preparation method of the described red temporarily water-soluble disperse dye of claim 2, it is characterized in that: described neutralization, accent intensity and stdn, its concrete method is: the temporarily water-soluble dispersion liquid that obtains, filtering separation obtains filter cake, behind the salt acid rinsing with pH=2 ~ 4, finally obtain the highly purified standardized filter cake for the treatment of, deionized water will be added then in the filter cake, be as the criterion stirring, making beating, slowly drip mass concentration 10% ~ 15% ammoniacal liquor afterwards and make it dissolving, add the aqueous water soluble disperse dyes that water is made into massfraction about 3 ~ 5% after the dissolving fully.
3. according to the preparation method of the described red temporarily water-soluble disperse dye of claim 2, it is characterized in that: diazo component, coupling component, its amount of substance ratio of Sodium Nitrite are: diazo component: coupling component: Sodium Nitrite=1:(1 ~ 1.05): 1.
4. the application of the described red temporarily water-soluble disperse dye of claim 1 in the preparation ink for ink-jet printer.
5. according to the application of the described red temporarily water-soluble disperse dye of claim 5 in the preparation ink for ink-jet printer, it is characterized in that adding ammoniacal liquor in ink is stablizer, adding glycol dimethyl ether or ethylene glycol is tensio-active agent, and adding JFC is a dispersion agent.
6. according to the application of the described red temporarily water-soluble disperse dye of claim 6, it is characterized in that described stabilizing agent dosage is 0.5% of an ink total mass, dosage of surfactant is 1% of an ink total mass, and dispersant dosage is 0.1% of an ink total mass.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011100584894A CN102161833A (en) | 2011-03-11 | 2011-03-11 | Red temporary water-soluble disperse dye and manufacturing method and use thereof |
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| CN2011100584894A CN102161833A (en) | 2011-03-11 | 2011-03-11 | Red temporary water-soluble disperse dye and manufacturing method and use thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113683904A (en) * | 2021-08-31 | 2021-11-23 | 沈阳化工研究院有限公司 | Red dye composition for dyeing and printing |
| CN113755030A (en) * | 2021-08-31 | 2021-12-07 | 沈阳化工研究院有限公司 | Red light blue liquid dye composition and application thereof in textile dyeing and printing |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1133320A (en) * | 1995-04-11 | 1996-10-16 | 大连理工大学 | Temporary soluble blue dispersed dye and synthesis method thereof |
| CN1136037A (en) * | 1996-03-01 | 1996-11-20 | 大连理工大学 | 2,6-dibromo-4-carboxysulfonateacyl aminobenzene and its synthesis |
| CN1215071A (en) * | 1997-10-22 | 1999-04-28 | 惠普公司 | Waterfast macromolecular chromophores using amphiphiles |
| US5922118A (en) * | 1996-06-14 | 1999-07-13 | Cabot Corporation | Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments |
| CN1289803A (en) * | 2000-10-25 | 2001-04-04 | 大连理工大学 | Temporarily water-soluble disperse dye containing carboxymethyl sulfonyl and its synthesis process |
-
2011
- 2011-03-11 CN CN2011100584894A patent/CN102161833A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1133320A (en) * | 1995-04-11 | 1996-10-16 | 大连理工大学 | Temporary soluble blue dispersed dye and synthesis method thereof |
| CN1136037A (en) * | 1996-03-01 | 1996-11-20 | 大连理工大学 | 2,6-dibromo-4-carboxysulfonateacyl aminobenzene and its synthesis |
| US5922118A (en) * | 1996-06-14 | 1999-07-13 | Cabot Corporation | Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments |
| CN1215071A (en) * | 1997-10-22 | 1999-04-28 | 惠普公司 | Waterfast macromolecular chromophores using amphiphiles |
| CN1289803A (en) * | 2000-10-25 | 2001-04-04 | 大连理工大学 | Temporarily water-soluble disperse dye containing carboxymethyl sulfonyl and its synthesis process |
Non-Patent Citations (3)
| Title |
|---|
| 无: "墨水的组成", 《办公自动化》 * |
| 朱谱新等: "《水基型喷墨打印墨水》", 31 December 2008, 中国纺织出版社 * |
| 郑庆康等: "喷墨着色剂的现状和发展趋势", 《染料工业》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113683904A (en) * | 2021-08-31 | 2021-11-23 | 沈阳化工研究院有限公司 | Red dye composition for dyeing and printing |
| CN113755030A (en) * | 2021-08-31 | 2021-12-07 | 沈阳化工研究院有限公司 | Red light blue liquid dye composition and application thereof in textile dyeing and printing |
| CN113755030B (en) * | 2021-08-31 | 2023-06-02 | 沈阳化工研究院有限公司 | Red light blue liquid dye composition and application thereof |
| CN113683904B (en) * | 2021-08-31 | 2023-06-13 | 沈阳化工研究院有限公司 | Red dye composition for dyeing and printing |
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Application publication date: 20110824 |