CN108102419B - Orange reactive dye suitable for digital ink-jet printing and preparation method thereof - Google Patents
Orange reactive dye suitable for digital ink-jet printing and preparation method thereof Download PDFInfo
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- CN108102419B CN108102419B CN201711375795.4A CN201711375795A CN108102419B CN 108102419 B CN108102419 B CN 108102419B CN 201711375795 A CN201711375795 A CN 201711375795A CN 108102419 B CN108102419 B CN 108102419B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
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Abstract
The invention relates to an orange reactive dye suitable for digital ink-jet printing and a preparation method thereof, wherein the dye has the following structural formula:
Description
Technical Field
The invention relates to a digital ink-jet printing reactive dye and a preparation method thereof. In particular to a digital ink-jet printing orange reactive dye and a preparation method thereof.
Background
At present, dyes used for digital ink-jet printing are common acid dyes and existing reactive dyes. Because the color light of the acid dye is not very bright, and the active group ethyl sulfonyl sulfate group of the reactive dye is very easy to hydrolyze, the digital ink-jet dye is unstable and is easy to corrode and block a spray head. The acid dye and the existing reactive dye can not meet the requirements of high-grade digital ink-jet printing dyes.
Disclosure of Invention
The technical problem to be solved by the invention is to provide the orange reactive dye for the digital ink-jet printing and the preparation method thereof, wherein the orange reactive dye does not corrode and block a spray head, reduces defective products, has low cost of required raw materials, and is bright in color, excellent in performance, convenient to use and strong in applicability.
In order to solve the technical problems, the invention provides an orange digital ink-jet printing reactive dye and a preparation method thereof, wherein the dye is a compound shown as the following formula (I):
in the formula: m is-H or an alkali metal, preferably the alkali metal is Na or K.
Specifically, the invention provides a method for preparing an orange digital ink-jet printing reactive dye, which comprises the following steps:
(a) 2.4-dissolution of sodium diaminobenzenesulfonate:
adding 2.4-diaminobenzene sulfonic acid sodium into water, stirring until the sodium 2.4-diaminobenzene sulfonic acid sodium is completely dissolved to obtain 2.4-diaminobenzene sulfonic acid sodium solution;
(b) a condensation reaction:
reacting cyanuric chloride with 2, 4-diaminobenzene sodium sulfonate at 0-8 ℃ for 4-6 hours, and controlling the pH of a reactant at 2-4 to obtain a condensed reaction solution;
preferably, crushed ice is added into water, cyanuric chloride is added, ice milling is carried out for 15 minutes, then 2, 4-diaminobenzene sodium sulfonate solution is dripped, sodium bicarbonate is used for maintaining the pH value at 2-4, the temperature is kept at 0-8 ℃, and reaction is carried out for 5 hours to obtain condensed reaction liquid;
(c) carrying out secondary condensation reaction:
adding aminoacetic acid into the first condensation reaction liquid in the step (b), uniformly stirring, raising the temperature to 30-45 ℃, reacting for 5-7 hours, and keeping the pH value of the reaction at 4-6.5 to obtain a second condensation reaction liquid;
preferably, the pH is maintained at 4-6.5 with sodium carbonate and the reaction is carried out for 6 hours;
(d) and (3) diazotization reaction of the secondary reaction solution:
adding hydrochloric acid and sodium nitrite into the secondary reaction solution in the step (c), and reacting for 1-3 hours at the temperature of 0-10 ℃.
Preferably, crushed ice is added into the reaction solution of the second condensation in the step (c), the temperature is controlled at 0 ℃, the mixture is stirred uniformly, after hydrochloric acid solution is added, sodium nitrite solution is added, and the reaction is carried out for 2 hours at the temperature of 0-10 ℃;
the reaction process always ensures that the Congo red test paper is blue after being soaked, the KI test paper is slightly blue after being soaked, and sulfamic acid is used for removing the residual sodium nitrite after the reaction is finished to obtain the diazonium salt of the secondary condensation reaction liquid;
(e) dissolving 3, 5-diaminobenzoic acid:
adding 3, 5-diaminobenzoic acid into water, uniformly stirring, and adjusting the pH value to 7 by using 30% sodium hydroxide to obtain a 3, 5-diaminobenzoic acid solution;
(f) one-step coupling reaction:
adding the diazonium salt of the secondary condensation reaction liquid into a 3, 5-diaminobenzoic acid solution, uniformly stirring, adjusting the pH value to 5-8 by using sodium carbonate, heating to 15-30 ℃, and reacting for 3-6 hours to obtain a one-step coupling reaction liquid;
(g) diazotization reaction of aniline-2, 5-disulfonic acid:
aniline-2, 5-disulfonic acid, hydrochloric acid and sodium nitrite are reacted at 0 to 10 ℃ for 1 to 3 hours.
Preferably, aniline-2, 5-disulfonic acid and crushed ice are added into water, the temperature is controlled at 0 ℃, the mixture is stirred uniformly, after hydrochloric acid solution is added, sodium nitrite solution is added, and the reaction is carried out for 2 hours at the temperature of 0-10 ℃.
Ensuring that the Congo red test paper is blue after being soaked, ensuring that the KI test paper is slightly blue after being soaked, and removing the residual sodium nitrite by using sulfamic acid after the reaction is finished to obtain aniline-2, 5-disulfonic acid diazonium salt;
(h) two-step coupling reaction:
adding aniline-2, 5-disulfonic acid diazonium salt into the product obtained in the step (f), uniformly stirring, adjusting the pH value to 5-8 by using sodium carbonate, heating to 15-30 ℃, reacting for 3-6 hours, and filtering to obtain a second-step coupling reaction solution; namely the digital ink-jet printing reactive orange dye.
Preferably, the method of the present invention may further comprise step (i):
(i) adjusting color light and intensity:
dyeing the material obtained in the step (h), and adjusting color light and intensity according to a dyeing result;
preferably, the method of the present invention may further comprise step (j):
(j) and (3) post-treatment:
and (e) adding activated carbon into the material obtained in the step (i), stirring for 1 hour, adding into a solid-liquid separator for separation, and collecting filtrate. Desalting the filtrate with nanofiltration membrane, concentrating the dye concentration in the feed liquid to 30% after the conductivity is reduced to 2000 μ S/cm, removing insoluble substances with ultrafiltration membrane, and detecting with microfiltration membrane (diameter 50mm, pore diameter 0.22 μm) for 20min until the permeability reaches 500 ml.
(k) Packaging a finished product:
packaging the article obtained in step (j).
The invention has the following beneficial effects:
the digital ink-jet printing reactive orange dye prepared by the preparation method has bright and beautiful chromatic light, excellent wet fastness properties, no corrosion and blockage of an ink-jet nozzle and simple and convenient operation.
Compared with acid dyes, the digital ink-jet printing reactive orange dye prepared by the preparation method disclosed by the invention is excellent in various fastnesses and environmental protection.
Detailed Description
To specifically illustrate the technical solution of the present invention, the technical solution of the present invention is described in detail below by referring to examples, which do not limit the present invention in any way.
Example 1
A digital ink-jet printing reactive orange dye has a structural formula as follows:
the preparation method of the digital ink-jet printing reactive orange dye comprises the following steps:
a. 2.4-dissolution of sodium diaminobenzenesulfonate: adding 300 liters of water into a reaction tank, adding 65kg of 2.4-diaminobenzene sulfonic acid sodium, and stirring until the mixture is completely dissolved to obtain a 2.4-diaminobenzene sulfonic acid sodium solution;
b. a condensation reaction: adding 300 liters of water and 500Kg of crushed ice into a reaction tank, stirring, adding 48Kg of cyanuric chloride, grinding for 15 minutes by using ice, then beginning to dropwise add a 2, 4-diaminobenzene sulfonic acid sodium salt solution, maintaining the PH at 2-4 by using sodium bicarbonate after dropwise adding, keeping the temperature at 0-8 ℃, and reacting for 5 hours to obtain a condensed reaction solution. Standby;
c. carrying out secondary condensation reaction: adding 20kg of aminoacetic acid into the first condensation reaction liquid obtained in the step (b), uniformly stirring, raising the temperature to 30-45 ℃, reacting for 5-7 hours, and keeping the pH value of the reaction at 4-6.5 to obtain a second condensation reaction liquid;
d. and (3) diazotization reaction of the secondary reaction solution: adding crushed ice into the reaction solution obtained in the second condensation step (c), and controlling the temperature at 0 ℃. Adding 76kg of 30% hydrochloric acid, adding 65kg of 30% sodium nitrite solution, reacting for 2 hours at the temperature of 0-10 ℃, ensuring that Congo red test paper is blue after being soaked and KI test paper is slightly blue during the reaction process, and removing the residual sodium nitrite by using sulfamic acid after the reaction is finished for later use;
e. dissolving 3, 5-diaminobenzoic acid:
37kg of 3, 5-diaminobenzoic acid is added into water, stirred evenly and adjusted to pH 7 by 30% sodium hydroxide to obtain the 3, 5-diaminobenzoic acid solution.
f. One-step coupling reaction: and (d) adding the product diazonium salt of the secondary condensation reaction liquid obtained in the step (d) into the product 3, 5-diaminobenzoic acid solution obtained in the step (e), and uniformly stirring. Adjusting pH to 5-8 with sodium carbonate, heating to 15-30 deg.C, reacting for 3 hr to obtain a coupling reaction solution;
g. diazotization reaction of aniline-2, 5-disulfonic acid:
400 liters of bottom water is added into a reaction tank, 133kg of aniline-2, 5-disulfonic acid is added, and the mixture is stirred uniformly. Crushed ice was added and the temperature was controlled at 0 ℃. Adding 74kg of 30% hydrochloric acid, adding 115kg of 30% sodium nitrite solution, reacting for 2 hours at the temperature of 0-10 ℃, ensuring that Congo red test paper is blue after being soaked and KI test paper is slightly blue during the reaction process, and removing the residual sodium nitrite by using sulfamic acid after the reaction is finished for later use;
h. two-step coupling reaction: and (f) adding the product aniline-2, 5-disulfonic acid diazonium salt obtained in the step (g) into the product one-step coupling reaction liquid obtained in the step (f), and uniformly stirring. Adjusting pH to 5-8 with sodium carbonate, heating to 15-30 deg.C, reacting for 3 hr to obtain coupling reaction solution, and filtering to obtain second-step coupling reaction solution; namely the digital ink-jet printing reactive orange dye.
i. Adjusting color light and intensity: and (5) dyeing the materials obtained in the step h, and adjusting the color light and the intensity according to the dyeing result.
j. And (3) post-treatment: and (e) adding 30kg of activated carbon into the material obtained in the step i, stirring for 1 hour, adding into a solid-liquid separator for separation, and collecting filtrate. Desalting the filtrate with nanofiltration membrane, concentrating the dye concentration in the feed liquid to 30% after the conductivity is reduced to 2000 μ S/cm, removing insoluble substances with ultrafiltration membrane, and detecting with microfiltration membrane (diameter 50mm, pore diameter 0.22 μm) for 20min until the permeability reaches 500 ml.
k. Packaging a finished product: and (e) packaging the article obtained in the step (j).
The digital ink-jet printing reactive orange dye prepared by the method of example 1 is 385 kilograms of standard dye.
Table one: example 1 application Performance and quality index of digital ink-jet printing reactive orange
The dyes and dye preparation processes of the present invention have been described by way of specific examples. The present invention may be implemented by appropriately changing the raw materials, process conditions, and the like by those skilled in the art in view of the content of the present invention, and the relevant changes may not be made without departing from the content of the present invention, and all similar substitutes and modifications apparent to those skilled in the art are deemed to be included in the scope of the present invention.
Claims (7)
1. An orange digital ink-jet printing reactive dye is characterized in that: the dye has the following structural formula:
in the formula: m is-H or an alkali metal.
2. The orange digital ink-jet printing reactive dye according to claim 1, characterized in that: and M is Na.
3. A method for preparing the orange digital ink-jet printing reactive dye as claimed in claim 1 or 2, which comprises the following steps:
(a) 2.4-dissolution of sodium diaminobenzenesulfonate:
adding 2.4-diaminobenzene sulfonic acid sodium into water, stirring until the sodium 2.4-diaminobenzene sulfonic acid sodium is completely dissolved to obtain 2.4-diaminobenzene sulfonic acid sodium solution;
(b) a condensation reaction:
reacting cyanuric chloride with 2, 4-diaminobenzene sodium sulfonate at 0-8 ℃ for 4-6 hours, and controlling the pH of a reactant at 2-4 to obtain a condensed reaction solution;
(c) carrying out secondary condensation reaction:
adding aminoacetic acid into the first condensation reaction liquid in the step (b), uniformly stirring, raising the temperature to 30-45 ℃, reacting for 5-7 hours, and keeping the pH value of the reaction at 4-6.5 to obtain a second condensation reaction liquid;
(d) and (3) diazotization reaction of the secondary reaction solution:
adding hydrochloric acid and sodium nitrite into the secondary condensation reaction liquid in the step (c), and controlling the temperature to be 0-10 ℃ to react for 1-3 hours; obtaining diazonium salt of the secondary condensation reaction liquid;
(e) dissolving 3, 5-diaminobenzoic acid:
adding 3, 5-diaminobenzoic acid into water, uniformly stirring, and adjusting the pH value to 7 by using 30% sodium hydroxide to obtain a 3, 5-diaminobenzoic acid solution;
(f) one-step coupling reaction:
adding the diazonium salt of the secondary condensation reaction liquid into a 3, 5-diaminobenzoic acid solution, uniformly stirring, adjusting the pH value to 5-8 by using sodium carbonate, heating to 15-30 ℃, and reacting for 3-6 hours to obtain a one-step coupling reaction liquid;
(g) diazotization reaction of aniline-2, 5-disulfonic acid:
reacting aniline-2, 5-disulfonic acid, hydrochloric acid and sodium nitrite at 0-10 ℃ for 1-3 hours;
(h) two-step coupling reaction:
adding aniline-2, 5-disulfonic acid diazonium salt into the product obtained in the step (f), uniformly stirring, adjusting the pH value to 5-8 by using sodium carbonate, heating to 15-30 ℃, reacting for 3-6 hours, and filtering to obtain a second-step coupling reaction solution; namely the digital ink-jet printing reactive orange dye.
4. The method of claim 3, wherein: also comprises the following steps:
(i) adjusting color light and intensity:
dyeing the material obtained in the step (h), and adjusting color light and intensity according to a dyeing result;
(j) and (3) post-treatment:
adding activated carbon into the material obtained in the step (i), stirring for 1 hour, adding the mixture into a solid-liquid separator for separation, collecting filtrate, desalting the filtrate by using a nanofiltration membrane, concentrating the dye concentration in the feed liquid to 30% after the conductivity is reduced to 2000 mu S/cm, removing insoluble substances by using an ultrafiltration membrane, and detecting the penetration amount of the ultrafiltration membrane for 20min to reach 500ml by using a microporous filtration membrane with the diameter of 50mm and the pore diameter of 0.22 mu m to obtain qualified product;
(k) packaging a finished product:
packaging the article obtained in step (j).
5. The method of claim 3, wherein step (b) is: adding crushed ice into water, adding cyanuric chloride, carrying out ice grinding for 15 minutes, then dropwise adding a 2, 4-diaminobenzene sulfonic acid sodium salt solution, maintaining the pH value at 2-4 by using sodium bicarbonate, keeping the temperature at 0-8 ℃, and reacting for 5 hours to obtain a condensed reaction liquid.
6. The method of claim 3, wherein step (d) is:
adding crushed ice into the secondary condensation reaction liquid in the step (c), controlling the temperature at 0 ℃, uniformly stirring, adding a hydrochloric acid solution, adding a sodium nitrite solution, and reacting for 2 hours at the temperature of 0-10 ℃;
and in the reaction process, the Congo red test paper is always ensured to be blue after being soaked, the KI test paper is slightly blue after being soaked, and the residual sodium nitrite is removed by sulfamic acid after the reaction is finished, so that the diazonium salt of the secondary condensation reaction solution is obtained.
7. The method of claim 3, wherein step (g) is:
adding aniline-2, 5-disulfonic acid and crushed ice into water, controlling the temperature at 0 ℃, uniformly stirring, adding a hydrochloric acid solution, adding a sodium nitrite solution, and reacting for 2 hours at the temperature of 0-10 ℃;
and (3) ensuring that the Congo red test paper is blue after being soaked and the KI test paper is slightly blue after being soaked in the reaction process, and removing the residual sodium nitrite by using sulfamic acid after the reaction is finished to obtain the aniline-2, 5-disulfonic acid diazonium salt.
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| CN108102419B true CN108102419B (en) | 2022-04-05 |
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| CN112457686B (en) * | 2019-09-06 | 2022-09-30 | 浙江科永化工有限公司 | Yellow reactive dye compound and preparation method and application thereof |
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| CN1745147A (en) * | 2003-02-05 | 2006-03-08 | 西巴特殊化学品控股有限公司 | Mixtures of reactive dyes and their use |
| CN104059000A (en) * | 2014-07-10 | 2014-09-24 | 浙江瑞华化工有限公司 | Reactive dye as well as preparation method and application thereof |
| CN104893357A (en) * | 2015-04-13 | 2015-09-09 | 华新珍 | Yellow reactive dye and preparation method thereof |
| CN105694530A (en) * | 2016-03-17 | 2016-06-22 | 浙江瑞华化工有限公司 | Orange reactive dye compound, orange reactive dye composition and preparation method and application thereof |
| CN106833015A (en) * | 2017-01-16 | 2017-06-13 | 台州市前进化工有限公司 | A kind of many chromophoric group dark brown reactive dye of trisazo- and its preparation method and application |
| CN106833011A (en) * | 2016-12-05 | 2017-06-13 | 泰兴锦云染料有限公司 | A kind of active orange dye and its preparation and application |
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2017
- 2017-12-19 CN CN201711375795.4A patent/CN108102419B/en active Active
Patent Citations (7)
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|---|---|---|---|---|
| CN1266869A (en) * | 1999-03-11 | 2000-09-20 | 西巴特殊化学品控股有限公司 | Azo dye, and its preparing process and use |
| CN1745147A (en) * | 2003-02-05 | 2006-03-08 | 西巴特殊化学品控股有限公司 | Mixtures of reactive dyes and their use |
| CN104059000A (en) * | 2014-07-10 | 2014-09-24 | 浙江瑞华化工有限公司 | Reactive dye as well as preparation method and application thereof |
| CN104893357A (en) * | 2015-04-13 | 2015-09-09 | 华新珍 | Yellow reactive dye and preparation method thereof |
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