CN108102419A - One kind is suitable for digital ink-jet printed orange active dye and preparation method thereof - Google Patents
One kind is suitable for digital ink-jet printed orange active dye and preparation method thereof Download PDFInfo
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- CN108102419A CN108102419A CN201711375795.4A CN201711375795A CN108102419A CN 108102419 A CN108102419 A CN 108102419A CN 201711375795 A CN201711375795 A CN 201711375795A CN 108102419 A CN108102419 A CN 108102419A
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Classifications
-
- 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
-
- 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)
- Ink Jet (AREA)
Abstract
The present invention relates to one kind to be suitable for digital ink-jet printed orange active dye and preparation method thereof, which has following structural formula：
Description
Technical field
The present invention relates to a kind of digital ink-jet printed reactive dye and preparation method thereof.It is especially a kind of digital ink-jet printed
Orange active dye and preparation method thereof.
Background technology
Typically now digital ink-jet printed dyestuff used is common acid dyes and existing reactive dye.Due to acidity
Dye shade is not very gorgeous, and the active group ethyl sulfuryl sulfuric acid ester base of reactive dye easily hydrolyzes, and causes digital ink-jet
Dyestuff is unstable, easy clog nozzle.Acid dyes and existing reactive dye have been unable to meet high-grade digital ink-jet printed
The demand of dyestuff.
The content of the invention
The technical problems to be solved by the invention are to provide a not clog nozzle, reduce defect ware, required raw material
It is at low cost and beautiful in colour, have excellent performance, it is easy to use, the digital ink-jet printed orange active dye of strong applicability and its
Preparation method.
In order to solve the above technical problem, the present invention provides a kind of orange digital ink-jet printed reactive dye and its preparations
Method, the dyestuff are such as following formula (I) compound represented：
In formula：M is-H either alkali metal, and preferred as alkali is Na or K.
Specifically, the present invention provides a kind of method for preparing orange digital ink-jet printed reactive dye, this method includes
Following steps：
(a) dissolving of 2.4- diamino benzene sulfonic acids sodium：
2.4- diamino benzene sulfonic acid sodium is added in water, is stirred to complete molten, is obtained 2.4- diamino benzene sulfonic acid sodium solutions；
(b) a contracting reaction：
At 0-8 DEG C, when making Cyanuric Chloride and 2.4- diamino benzene sulfonic acids sodium reaction 4-6 small, the pH controls of reactant exist
2-4 obtains a contracting reaction solution；
Preferably, trash ice is added in water, adds in Cyanuric Chloride, is carried out ice and is ground 15 minutes, 2.4- diaminos are then added dropwise
Base benzene sulfonic acid sodium salt solution maintains pH in 2-4 with sodium acid carbonate, and temperature is kept for 0-8 DEG C, when reaction 5 is small after, obtain a contracting reaction solution；
(c) two contracting reaction：
In (b) step 1 contracting reaction solution, amion acetic acid is added in, is stirred evenly, temperature is risen to 30-45 DEG C, reacts 5-7
Hour, the pH value of reaction is maintained at 4-6.5, obtains two contracting reaction solutions；
Preferably, pH=4-6.5 is maintained with sodium carbonate, when reaction 6 is small；
(d) two contracting reaction solution diazo-reaction：
In (c) step 2 contracting reaction solution, hydrochloric acid and sodium nitrite are added in, temperature control is when 0-10 DEG C of reaction 1-3 is small.
Preferably, trash ice is added in (c) step 2 contracting reaction solution, temperature is controlled at 0 DEG C, stirred evenly, and adds in hydrochloric acid
After solution, sodium nitrite solution is added in, when 0-10 DEG C of temperature, reaction 2 are small；
Reaction process is in blueness after ensuring Congored test paper leaching always, and in micro- blueness after the leaching of KI test paper, reaction, which finishes, uses ammonia
Base sulfonic acid removes remaining sodium nitrite, obtains two contracting reaction solution diazols；
(e) dissolving of 3,5- diaminobenzoic acids：
3,5- diaminobenzoic acids are added in water, are stirred evenly, and with 30% sodium hydroxide tune pH=7, obtain 3,5- bis-
Aminobenzoic acid solution；
(f) a step coupling reaction：
Two contracting reaction solution diazols are added in 3,5- diaminobenzoic acid solution, are stirred evenly, with sodium carbonate tune pH
=5-8 is warming up to 15-30 DEG C, when reaction 3~6 is small, obtains a step coupling reaction liquid；
(g) aniline -2,5- disulfonic acid diazo-reaction：
At 0-10 DEG C, when making aniline -2,5- disulfonic acid, hydrochloric acid and sodium nitrite reaction 1-3 small.
Preferably, aniline -2,5- disulfonic acid and trash ice are added in water, temperature is controlled at 0 DEG C, stirred evenly, and adds in hydrochloric acid
After solution, sodium nitrite solution is added in, when 0-10 DEG C of temperature, reaction 2 are small.
Reaction process is in blueness after ensuring Congored test paper leaching always, and in micro- blueness after the leaching of KI test paper, reaction, which finishes, uses ammonia
Base sulfonic acid removes remaining sodium nitrite, obtains aniline -2,5- disulfonic acid diazol；
(h) two step coupling reaction：
Aniline -2,5- disulfonic acid diazol is added in the product of step (f) acquisition, stirred evenly, with sodium carbonate tune
PH=5-8, is warming up to 15-30 DEG C, when reaction 3~6 is small, and filtering obtains two step coupling reaction liquid；I.e. digital ink-jet printed reactive orange
Dyestuff.
Preferably, method of the invention can also include step (i)：
(i) coloured light and intensity are adjusted：
(h) step material is dyed, carries out coloured light further according to coloration result, intensity adjusts；
Preferably, method of the invention can also include step (j)：
(j) post-process：
Add in activated carbon in the material obtained by (i) step, when stirring 1 is small after, be added in solid-liquid separator and divided
From collection filtrate.By filtrate by NF membrane desalination, dye strength in feed liquid is concentrated after electrical conductivity is down to 2000 μ S/cm
To 30%, insoluble matter is removed finally by ultrafiltration membrane, it is saturating with micropore filtering film (diameter 50mm, 0.22 μm of aperture) detection 20min
It is qualification excessively to reach 500ml.
(k) finished product packing：
Article obtained by (j) step is packed.
Advantageous effect possessed by the present invention：
The preparation method of the present invention, prepared digital ink-jet printed active orange dye have bright-coloured beautiful coloured light, respectively
Item wet fastness properties is very superior, not clog inkjet head, and easy to operate.
Digital ink-jet printed active orange dye prepared by the preparation method of the present invention, in ink-jet reactive dye, with acid
Property dyestuff compare, either every fastness is still to being all excellent in terms of environmental protection.
Specific embodiment
To illustrate technical scheme, embodiment is set forth below and carrys out the technical solution that the present invention will be described in detail,
The embodiment does not form any limitation of the invention.
Embodiment 1
A kind of digital ink-jet printed active orange dye, the structural formula of the dyestuff are：
The preparation method of the digital ink-jet printed active orange dye, includes the following steps：
A, the dissolving of 2.4- diamino benzene sulfonic acids sodium：Add 300 liters of water into retort, add in 2.4- diamino benzene sulfonic acid sodium
65kg stirs to complete molten, obtains 2.4- diamino benzene sulfonic acid sodium solutions；
B, a contracting reaction：Into retort plus 300 liters, trash ice 500Kg of water, stirring, addition Cyanuric Chloride 48kg, ice grind 15
After minute, start that 2.4- diamino benzene sulfonic acid sodium solutions are added dropwise, be added dropwise, maintaining PH with sodium acid carbonate, temperature is kept in 2-4
0-8 DEG C, reaction 5 it is small when after, obtain a contracting reaction solution.It is spare；
C, two contracting reaction：In (b) step 1 contracting reaction solution, amion acetic acid 20kg is added in, stirs evenly, temperature is risen to
30-45 DEG C, when reaction 5-7 is small, the pH value of reaction is maintained at 4-6.5, obtains two contracting reaction solutions；
D, two contracting reaction solution diazo-reaction：In (c) step 2 contracting reaction solution, trash ice is added in, temperature is controlled at 0 DEG C.
30% hydrochloric acid 76kg is added in, then adds 30% sodium nitrite solution 65kg, in 0-10 DEG C of temperature, when reaction 2 is small, reaction process
Always ensure after Congored test paper leaching in blueness, in micro- blueness after the leaching of KI test paper, reaction finish removed with sulfamic acid it is remaining sub-
Sodium nitrate, it is spare；
E, the dissolving of 3,5- diaminobenzoic acids：
3,5- diaminobenzoic acid 37kg are added in water, are stirred evenly, and with 30% sodium hydroxide tune PH=7, obtain 3,5-
Diaminobenzoic acid solution.
F, a step coupling reaction：The two contracting reaction solution diazol of product that step (d) is obtained is added to step (e) acquisition
Product 3, in 5- diaminobenzoic acid solution, stir evenly.With sodium carbonate tune PH=5-8,15-30 DEG C is warming up to, reaction 3 is small
When, a step coupling reaction liquid is obtained, it is spare；
G, aniline -2,5- disulfonic acid diazo-reaction：
In retort plus 400 liters of bottom water, addition 133kg aniline -2,5- disulfonic acid stir evenly.Add in trash ice, temperature
Control is at 0 DEG C.30% hydrochloric acid 74kg is added in, then adds 30% sodium nitrite solution 115kg, in 0-10 DEG C of temperature, reaction 2 is small
When, reaction process ensures that Congored test paper, in blueness, in micro- blueness after the leaching of KI test paper, reacts to finish and uses sulfamic acid after soaking always
Remaining sodium nitrite is removed, it is spare；
H, two step coupling reaction：Product aniline -2,5- disulfonic acid diazol that step (g) is obtained, is added to step f and obtains
In the one step coupling reaction liquid of product obtained, stir evenly.With sodium carbonate tune PH=5-8,15-30 DEG C, when reaction 3 is small is warming up to,
Coupling reaction liquid is obtained, filtering obtains two step coupling reaction liquid；I.e. digital ink-jet printed active orange dye.
I, coloured light and intensity are adjusted：H steps material is dyed, carries out coloured light further according to coloration result, intensity adjusts.
J, post-process：In the material obtained by i steps add in 30kg activated carbons, stirring 1 it is small when after, be added to separation of solid and liquid
It is separated in device, collects filtrate.By filtrate by NF membrane desalination, will be contaminated after electrical conductivity is down to 2000 μ S/cm in feed liquid
Material concentration is concentrated into 30%, removes insoluble matter finally by ultrafiltration membrane, is examined with micropore filtering film (diameter 50mm, 0.22 μm of aperture)
It is qualification to survey 20min transit doses to reach 500ml.
K, finished product packing：Article obtained by j steps is packed.
Digital ink-jet printed active orange dye prepared by the method for embodiment 1 is 385 kilograms of standard dyes.
Table one：1 digital ink-jet printed reactive orange application performance of embodiment, quality index
The dyestuff and dyestuff preparation method of the present invention is described by specific embodiment.People in the art
Member can use for reference the links such as the appropriate feed change of present disclosure, process conditions to realize the present invention, and correlation, which changes, all not to be had
There is disengaging present disclosure, all similar replacements and change are it will become apparent to those skilled in the art that all
It is deemed to be included within the scope of the present invention.
Claims (7)
1. a kind of orange digital ink-jet printed reactive dye, it is characterised in that：The dyestuff has following structural formula：
In formula：M is-H either alkali metal.
2. orange digital ink-jet printed reactive dye according to claim 1, it is characterised in that：The M is Na.
A kind of 3. preparation method of the orange digital ink-jet printed reactive dye of claim 1 or 2, which is characterized in that the party
Method includes the following steps：
(a) dissolving of 2.4- diamino benzene sulfonic acids sodium：
2.4- diamino benzene sulfonic acid sodium is added in water, is stirred to complete molten, is obtained 2.4- diamino benzene sulfonic acid sodium solutions；
(b) a contracting reaction：
At 0-8 DEG C, when making Cyanuric Chloride and 2.4- diamino benzene sulfonic acids sodium reaction 4-6 small, the pH of reactant is controlled in 2-4,
Obtain a contracting reaction solution；
(c) two contracting reaction：
In (b) step 1 contracting reaction solution, amion acetic acid is added in, is stirred evenly, temperature is risen to 30-45 DEG C, reaction 5-7 is small
When, the pH value of reaction is maintained at 4-6.5, obtains two contracting reaction solutions；
(d) two contracting reaction solution diazo-reaction：
In (c) step 2 contracting reaction solution, hydrochloric acid and sodium nitrite are added in, temperature control is when 0-10 DEG C of reaction 1-3 is small；It obtains
Two contracting reaction solution diazols；
(e) dissolving of 3,5- diaminobenzoic acids：
3,5- diaminobenzoic acids are added in water, are stirred evenly, and with 30% sodium hydroxide tune pH=7, obtain 3,5- diaminobenzenes
Formic acid solution；
(f) a step coupling reaction：
Two contracting reaction solution diazols are added in 3,5- diaminobenzoic acid solution, are stirred evenly, with sodium carbonate tune pH=5-
8,15-30 DEG C is warming up to, when reaction 3~6 is small, obtains a step coupling reaction liquid；
(g) aniline -2,5- disulfonic acid diazo-reaction：
At 0-10 DEG C, when making aniline -2,5- disulfonic acid, hydrochloric acid and sodium nitrite reaction 1-3 small；
(h) two step coupling reaction：
Aniline -2,5- disulfonic acid diazol is added in the product of step (f) acquisition, stirred evenly, with sodium carbonate tune pH=
5-8, is warming up to 15-30 DEG C, when reaction 3~6 is small, and filtering obtains two step coupling reaction liquid；I.e. digital ink-jet printed reactive orange dye
Material.
4. method as claimed in claim 3, it is characterised in that：Further include following steps：
(i) coloured light and intensity are adjusted：
(h) step material is dyed, carries out coloured light further according to coloration result, intensity adjusts.
(j) post-process：
Add in activated carbon in the material obtained by (i) step, when stirring 1 is small after, be added in solid-liquid separator and separated, received
Collect filtrate.By filtrate by NF membrane desalination, dye strength in feed liquid is concentrated into after electrical conductivity is down to 2000 μ S/cm
30%, insoluble matter is removed finally by ultrafiltration membrane, is penetrated with micropore filtering film (diameter 50mm, 0.22 μm of aperture) detection 20min
It is qualification that amount, which reaches 500ml,.
(k) finished product packing：
Article obtained by (j) step is packed.
5. according to the method described in claim 3, it is characterized in that, (b) step is：Trash ice is added in water, adds in three
Polychlorostyrene cyanogen carries out ice and grinds 15 minutes, 2.4- diamino benzene sulfonic acid sodium solutions are then added dropwise, and pH is maintained in 2-4, temperature with sodium acid carbonate
Degree keep 0-8 DEG C, reaction 5 it is small when after, obtain a contracting reaction solution.
6. according to the method described in claim 3, it is characterized in that, (d) step is：
Trash ice is added in (c) step 2 contracting reaction solution, temperature is controlled at 0 DEG C, stirred evenly, and after adding in hydrochloric acid solution, is added in
Sodium nitrite solution, when 0-10 DEG C of temperature, reaction 2 are small；
Reaction process is in blueness after ensuring Congored test paper leaching always, is finished after the leaching of KI test paper in micro- blueness, reaction with amino sulphur
Acid removes remaining sodium nitrite, obtains two contracting reaction solution diazols.
7. according to the method described in claim 3, it is characterized in that, (g) step is：
In water plus aniline -2,5- disulfonic acid and trash ice, temperature are controlled at 0 DEG C, stirred evenly, and after adding in hydrochloric acid solution, are added in
Sodium nitrite solution, when 0-10 DEG C of temperature, reaction 2 are small；
Reaction process is in blueness after ensuring Congored test paper leaching always, is finished after the leaching of KI test paper in micro- blueness, reaction with amino sulphur
Acid removes remaining sodium nitrite, obtains aniline -2,5- disulfonic acid diazol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711375795.4A CN108102419B (en) | 2017-12-19 | 2017-12-19 | Orange reactive dye suitable for digital ink-jet printing and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711375795.4A CN108102419B (en) | 2017-12-19 | 2017-12-19 | Orange reactive dye suitable for digital ink-jet printing and preparation method thereof |
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| Publication Number | Publication Date |
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| CN108102419A true CN108102419A (en) | 2018-06-01 |
| CN108102419B CN108102419B (en) | 2022-04-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201711375795.4A Active CN108102419B (en) | 2017-12-19 | 2017-12-19 | Orange reactive dye suitable for digital ink-jet printing and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112457686A (en) * | 2019-09-06 | 2021-03-09 | 浙江科永化工有限公司 | Yellow reactive dye compound and preparation method and application thereof |
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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 |
| 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 |
-
2017
- 2017-12-19 CN CN201711375795.4A patent/CN108102419B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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| 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 |
| 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 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112457686A (en) * | 2019-09-06 | 2021-03-09 | 浙江科永化工有限公司 | Yellow reactive dye compound and preparation method and application thereof |
| 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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| Publication number | Publication date |
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| CN108102419B (en) | 2022-04-05 |
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