CN103554980A - Red reactive dye and preparation method thereof - Google Patents
Red reactive dye and preparation method thereof Download PDFInfo
- Publication number
- CN103554980A CN103554980A CN201310465381.6A CN201310465381A CN103554980A CN 103554980 A CN103554980 A CN 103554980A CN 201310465381 A CN201310465381 A CN 201310465381A CN 103554980 A CN103554980 A CN 103554980A
- Authority
- CN
- China
- Prior art keywords
- reaction
- add
- solution
- formula
- structural formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 CC1C(*)CC(*)CC1 Chemical compound CC1C(*)CC(*)CC1 0.000 description 4
Landscapes
- Coloring (AREA)
Abstract
The invention relates to a red reactive dye and a preparation method thereof, and the red reactive has a molecular structure shown as a formula (I). The red reactive dye has good water solubility, high degree of dyeing, wet processing fastness resisting wet friction, and no wastewater discharge in a printing and dyeing process.
Description
Technical field
The invention belongs to reactive dyestuffs field, particularly relate to a kind of red reactive dyes and preparation method thereof, this dyestuff goes for digital ink-jet printed pure cotton dyeing.
Background technology
Reactive dyestuffs are beautiful in colour with it, application convenient,, with covalent bonds, have excellent fastness ability and are applied to more and more widely dyeing process with fiber.Along with the exploitation of its application performance, the dyeing of reactive dyestuffs has spreaded all over the dyeing of the fabrics such as cotton, hair, fiber crops, nylon, silk, and its range of application is more and more extensive.The object of this invention is to provide a kind of red reactive dyes, this dyestuff has good water-soluble, high dye uptake, and the wet colour fastness of moisture-proof friction, and orchil is one of dominant hue of dyestuff, is the dye of current cellulose dyeing consumption maximum.Be applicable to pure cotton dyeing, as be applicable to digital ink-jet printed pure cotton dyeing.
Summary of the invention
The technical problem to be solved in the present invention is: provide a kind of have good water-soluble, high dye uptake, wet colour fastness red reactive dyes of moisture-proof friction and preparation method thereof.
The technical solution used in the present invention is:
, its molecular structure is as shown in formula I:
Wherein R1 is following structural formula (1-1) to the arbitrary substituting group in structural formula (1-5):
Wherein R2 is following structural formula (2-1) to the arbitrary substituting group in structural formula (2-2):
M is H or basic metal.Preferably, described M be-H or-Na or-K.
Preferably, described R
1for formula (1-2) substituting group; R
2substituting group for formula (2-2).
The present invention also provides the preparation method of the compound of said structure formula I, comprises the steps:
One, a contracting reaction:
To on the rocks in reactor, cyanuric chloride, ice mill cyanuric chloride is after five minutes, drip the H acid solution dissolved, make it at condensation course, control ℃-5 ℃, temperature T=0, pH=6.0-6.5, react laminate analysis after 4.5 hours, after qualified a step condenses, carry out next step reaction.
Two, two contracting reactions:
Any compound in following structural formula is joined in a step condenses, heats up, with soda ash, control the pH value of two contracting reactants, reaction end take following raw material reaction complete be terminal, obtain two step condensess.
Three, diazotization reaction:
Any compound in following structural formula is dissolved with sheet alkali (NaOH), then add hydrochloric acid, on the rocks, add fast sodium nitrite solution to carry out diazotization reaction, temperature 0-5 ℃ in diazotization reaction process, it is blue keeping starch potassium iodide paper, obtains diazonium salt after having reacted.
Four, coupled reaction
Step 3 gained diazonium salt is dripped slowly in the two contracting things that add step 2 gained, in dropping process, with the pH=6.0-8.0 of 15% soda ash solution regulator solution, it is qualified after 2.0-3.0 hour to react, and makes the dye solution of structure formula I.
Preferably, this preparation method also comprises the steps:
Five, refining
By synthetic dyestuff acid adjustment, then salt adding is saltoutd, and filters to obtain filter cake, and the filter cake solid content of dyestuff is reached more than 60%, and dyestuff filter cake is dissolved in free of contamination stainless cylinder of steel, adds auxiliary agent, filters to obtain work in-process dyestuff.
Six, carry out aftertreatment desalination:
The work in-process dyestuff of removing by product is carried out to blending processing, make it reach the requirement of standard.Then dye solution is carried out to semi-permeable membranes and carry out desalination, add sanitas, pH value conditioning agent, sterilant, viscosity modifier, waterproof enzymolysis auxiliary agent after having removed salt.Qualified rear packaging final prod after testing.
Dyestuff of the present invention goes for cotton fiber dyeing, as is applicable to digital ink-jet printed pure cotton dyeing.
The beneficial effect that the present invention has:
Red reactive dyes of the present invention has good water-soluble, high dye uptake, the wet colour fastness of moisture-proof friction, non-wastewater discharge in dyeing process.
Embodiment
In order to understand the present invention, with specific embodiment, further illustrate the present invention below, but do not limit the present invention.
Embodiment 1
, this dyestuff has formula II structural formula:
The preparation method of this dyestuff, comprises the steps:
One, a step condensation reaction: add end water 4500L in 10 tons of tanks, sodium hydroxide solution with 40% makes H acid dry powder 1260KG furnishing solution the pH=7.0 of solution, in 35 tons of tanks, add end water 4000L, add 3 tons of ice, cyanuric chloride 610KG is joined in 35 tons of retort and stirred, in 35 tons of retort, drip H acid solution, in dropping process, with sodium hydroxide solution, control the pH=3.0-2.5 of a step condensation reaction.Drip temperature in H acid process and be controlled at T=0 ℃-10 ℃, after dripping off, carry out laminate analysis, qualified after, obtain a step condenses, treat two step condensation reactions.
Two, two step condensation reactions;
In step 1 gained one step condenses, directly add 2-amino-5-β hydroxyethyl sulfone sulfate base Phenylsulfonic acid 550KG, add rear with soda ash (Na
2cO
3) solution controls the pH=5.0-7.0 of reactant, is warmed up to ℃-40 ℃, temperature T=30, reacts after 5 hours, obtains two step condensess after qualified by liquid chromatographic detection, treats coupled reaction;
Three, diazotization reaction:
In 10 tons of tanks, add end water 4000L, then 2-amino-6-β hydroxyethyl sulfone sulfate base naphthene sulfonic acid 740KG is added, add hydrochloric acid, add 2 tons of ice, stir and add fast sodium nitrite solution, in diazo process, with starch potassium iodide paper check, keep Sodium Nitrite excessive, temperature is controlled at T=0 ℃-5 ℃, reacts 3 hours, then with thionamic acid, removes excessive nitrous acid, obtain diazonium salt, treat coupled reaction.
Four, coupled reaction:
Step 3 gained diazonium salt is dripped slowly in the two step condensess that join step 2 gained, in dropping process, with the pH=6.0-8.0 of 15% soda ash solution regulator solution, react qualified after 3.0 hours, make structure formula II dye solution.
Five, saltout:
After completion of the reaction, add the sodium-chlor of volume 25% to saltout, press filtration after saltouing 2 hours, obtains filter cake, weighs.Dyestuff filter cake is dissolved in free of contamination stainless cylinder of steel, add auxiliary agent, filter to obtain work in-process dyestuff.
Six, carry out aftertreatment desalination:
The work in-process dyestuff of removing by product is carried out to blending processing, make it reach the requirement of standard.Then dye solution is carried out to semi-permeable membranes and carry out desalination, add sanitas, pH value conditioning agent, sterilant, viscosity modifier, waterproof enzymolysis auxiliary agent after having removed salt.Qualified rear packaging final prod after testing.
2 one kinds of red reactive dyes of embodiment, this dyestuff has following formula III structural formula:
The preparation method of this dyestuff, comprises the steps:
Contracting reaction in one: one:
In 10 tons of tanks, add end water 4500L, sodium hydroxide solution with 40% makes H acid dry powder 1260KG furnishing solution the pH=7.0 of solution, in 35 tons of tanks, add end water 4000L, add 3 tons of ice that cyanuric chloride 610KG is joined in 35 tons of retort and stirred, in 35 tons of retort, drip H acid solution, in dropping process, with sodium hydroxide solution, control the pH=3.0-2.5 of a step condensation reaction.Drip temperature in H acid process and be controlled at T=0 ℃-10 ℃. after dripping off, carry out laminate analysis, qualified after, obtain a step condenses, treat two step condensation reactions.
Two, two step condensation reactions;
In a step condenses of step 1 gained, directly add p-β hydroxyethyl sulfone sulfate base aniline 295KG, add the rear pH=5.0-7.0 that controls reactant with soda ash solution, be warmed up to ℃-40 ℃, temperature T=30, react after 5 hours, after qualified by liquid chromatographic detection, obtain two step condensess, treat coupled reaction.
Three, diazotization reaction:
In 10 tons of tanks, add end water 4000L, then will add 2-amino-5-β hydroxyethyl sulfone sulfate base Phenylsulfonic acid 560KG, add hydrochloric acid, add 2 tons of ice, stir and add fast sodium nitrite solution, in diazo process, with starch potassium iodide paper check, keep Sodium Nitrite excessive, temperature is controlled at T=0 ℃-5 ℃, reacts 3 hours, then with thionamic acid, removes excessive nitrous acid, obtain diazonium salt, treat coupled reaction.
Four, coupled reaction:
The diazonium salt of step 3 gained is dripped slowly in the two step condensess that join step 2 gained, in dropping process with the pH=6.0-8.0 of 15% soda ash solution regulator solution, it is qualified after 2.0-3.0 hour to react, and makes structure formula III dye solution.
Five, saltout:
After completion of the reaction, add the sodium-chlor of volume 25% to saltout, press filtration after saltouing 2 hours, obtains filter cake, weighs.Dyestuff filter cake is dissolved in free of contamination stainless cylinder of steel, add auxiliary agent, filter to obtain work in-process dyestuff.
Six, carry out aftertreatment desalination:
The work in-process dyestuff of removing by product is carried out to blending processing, make it reach the requirement of standard.Then dye solution is carried out to semi-permeable membranes and carry out desalination, add sanitas, pH value conditioning agent, sterilant, viscosity modifier, waterproof enzymolysis auxiliary agent after having removed salt.Qualified rear packaging final prod after testing.
3 one kinds of red reactive dyes of embodiment, this dyestuff has following formula IV structural formula:
The preparation method of this dyestuff, comprises the steps:
Contracting reaction in one: one:
In 10 tons of tanks, add end water 4500L, sodium hydroxide solution with 40% makes H acid dry powder 1260KG furnishing solution the pH=7.0 of solution, in 35 tons of tanks, add end water 4000L, add 3 tons of ice that cyanuric chloride 610KG is joined in 35 tons of retort and stirred, in 35 tons of retort, drip H acid solution, in dropping process, with sodium hydroxide solution, control the pH=3.0-2.5 of a step condensation reaction.Drip temperature in H acid process and be controlled at T=0 ℃-10 ℃. after dripping off, carry out laminate analysis, qualified after, obtain a step condenses, treat two step condensation reactions.
Two, two step condensation reactions;
In a step condenses of step 1 gained, directly add 2-amino-5-β hydroxyethyl sulfone sulfate base Phenylsulfonic acid 550KG, add the rear pH=5.0-7.0 that controls reactant with soda ash solution, be warmed up to ℃-40 ℃, temperature T=30, react after 5 hours, after qualified by liquid chromatographic detection, obtain two step condensess, treat coupled reaction.
Three, diazotization reaction:
In 10 tons of tanks, add end water 4000L, then will add p-β hydroxyethyl sulfone sulfate base aniline 281KG, add hydrochloric acid, add 2 tons of ice, stir and add fast sodium nitrite solution, in diazo process, with starch potassium iodide paper check, keep Sodium Nitrite excessive, temperature is controlled at T=0 ℃-5 ℃, reacts 3 hours, then with thionamic acid, removes excessive nitrous acid, obtain diazonium salt, treat coupled reaction.
Four, coupled reaction:
The diazonium salt of step 3 gained is dripped slowly in the two step condensess that join step 2 gained, in dropping process with the pH=6.0-8.0 of 15% soda ash solution regulator solution, it is qualified after 2.0-3.0 hour to react, and makes structure formula III dye solution.
Five, saltout:
After completion of the reaction, add the sodium-chlor of volume 25% to saltout, press filtration after saltouing 2 hours, obtains filter cake, weighs.Dyestuff filter cake is dissolved in free of contamination stainless cylinder of steel, add auxiliary agent, filter to obtain work in-process dyestuff.
Six, carry out aftertreatment desalination:
The work in-process dyestuff of removing by product is carried out to blending processing, make it reach the requirement of standard.Then dye solution is carried out to semi-permeable membranes and carry out desalination, add sanitas, pH value conditioning agent, sterilant, viscosity modifier, waterproof enzymolysis auxiliary agent after having removed salt.Qualified rear packaging final prod after testing.
The application performance table of the red reactive dyes that embodiment 1 makes is as follows:
The application performance table of the red reactive dyes that embodiment 2 makes is as follows:
The application performance table of the red reactive dyes that embodiment 3 makes is as follows:
Method of the present invention is described by specific embodiment.Those skilled in the art can use for reference the links such as content appropriate change raw material of the present invention, processing condition and realize corresponding other object, its relevant change does not all depart from content of the present invention, within all similar replacements and change will become apparent to those skilled in the art that and be all deemed to be included in scope of the present invention.
Claims (4)
1. a red reactive dyes, is characterized in that: its molecular structure is as shown in formula I:
Wherein R1 is following structural formula (1-1) to the arbitrary substituting group in structural formula (1-5):
Wherein R2 is following structural formula (2-1) to the arbitrary substituting group in structural formula (2-2):
M is H or basic metal.
2. a kind of red reactive dyes according to claim 1, is characterized in that: described M for-H or-Na or-K.
3. according to a kind of red reactive dyes described in claim 1 or 2, it is characterized in that: described R
1for formula (1-2) substituting group; R
2substituting group for formula (2-2).
4. the preparation method of red reactive dyes described in claim 1, is characterized in that: comprise the steps:
One, a contracting reaction:
To on the rocks in reactor, cyanuric chloride, ice mill cyanuric chloride is after five minutes, drip the H acid solution dissolved, make it at condensation course, control ℃-5 ℃, temperature T=0, pH=6.0-6.5, react laminate analysis after 4.5 hours, after qualified a step condenses, carry out next step reaction.
Two, two contracting reactions:
Any compound in following structural formula is joined in a step condenses, heats up, with soda ash, control the pH value of two contracting reactants, reaction end take following raw material reaction complete be terminal, obtain two step condensess.
Three, diazotization reaction:
Any compound in following structural formula is dissolved with sheet alkali (NaOH), then add hydrochloric acid, on the rocks, add fast sodium nitrite solution to carry out diazotization reaction, temperature 0-5 ℃ in diazotization reaction process, it is blue keeping starch potassium iodide paper, obtains diazonium salt after having reacted.
Four, coupled reaction
Step 3 gained diazonium salt is dripped slowly in the two contracting things that add step 2 gained, in dropping process, with the pH=6.0-8.0 of 15% soda ash solution regulator solution, it is qualified after 2.0-3.0 hour to react, and makes the dye solution of structure formula I.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310465381.6A CN103554980A (en) | 2013-09-29 | 2013-09-29 | Red reactive dye and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310465381.6A CN103554980A (en) | 2013-09-29 | 2013-09-29 | Red reactive dye and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103554980A true CN103554980A (en) | 2014-02-05 |
Family
ID=50009353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310465381.6A Pending CN103554980A (en) | 2013-09-29 | 2013-09-29 | Red reactive dye and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103554980A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105504868A (en) * | 2015-12-02 | 2016-04-20 | 天津德凯化工股份有限公司 | Red reactive dye |
| CN116004032A (en) * | 2022-12-30 | 2023-04-25 | 上海雅运新材料有限公司 | Red dye compound and synthetic method and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0094055A1 (en) * | 1982-05-12 | 1983-11-16 | Hoechst Aktiengesellschaft | Monoazo compounds, process for their preparation and their use as dyestuffs |
| US5980590A (en) * | 1995-12-28 | 1999-11-09 | Dystar Texilfarben Gmbh & Co. Deutschland Kg | Dyestuff mixtures of water-soluble fiber-reactive azo dyestuffs, processes for their preparation and their use |
| CN1511886A (en) * | 2002-12-27 | 2004-07-14 | 上海染料化工八厂 | Red dye composition and its preparation and use |
| CN101497747A (en) * | 2008-02-02 | 2009-08-05 | 上海雅运纺织化工有限公司 | Red reactive dye composition and application thereof |
| CN102757667A (en) * | 2011-04-26 | 2012-10-31 | 上海雅运纺织化工股份有限公司 | Red reactive dye composition and dyeing application thereof on fiber |
| CN102964870A (en) * | 2012-10-25 | 2013-03-13 | 浙江龙盛集团股份有限公司 | Active black dye composition |
-
2013
- 2013-09-29 CN CN201310465381.6A patent/CN103554980A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0094055A1 (en) * | 1982-05-12 | 1983-11-16 | Hoechst Aktiengesellschaft | Monoazo compounds, process for their preparation and their use as dyestuffs |
| US5980590A (en) * | 1995-12-28 | 1999-11-09 | Dystar Texilfarben Gmbh & Co. Deutschland Kg | Dyestuff mixtures of water-soluble fiber-reactive azo dyestuffs, processes for their preparation and their use |
| CN1511886A (en) * | 2002-12-27 | 2004-07-14 | 上海染料化工八厂 | Red dye composition and its preparation and use |
| CN101497747A (en) * | 2008-02-02 | 2009-08-05 | 上海雅运纺织化工有限公司 | Red reactive dye composition and application thereof |
| CN102757667A (en) * | 2011-04-26 | 2012-10-31 | 上海雅运纺织化工股份有限公司 | Red reactive dye composition and dyeing application thereof on fiber |
| CN102964870A (en) * | 2012-10-25 | 2013-03-13 | 浙江龙盛集团股份有限公司 | Active black dye composition |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105504868A (en) * | 2015-12-02 | 2016-04-20 | 天津德凯化工股份有限公司 | Red reactive dye |
| CN105504868B (en) * | 2015-12-02 | 2020-01-21 | 天津德凯化工股份有限公司 | Red reactive dye |
| CN116004032A (en) * | 2022-12-30 | 2023-04-25 | 上海雅运新材料有限公司 | Red dye compound and synthetic method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103554976A (en) | Red reactive dye and preparation method thereof | |
| CN110938039A (en) | Purple reactive dye based on trisazo multichromosome and preparation and application thereof | |
| CN103554980A (en) | Red reactive dye and preparation method thereof | |
| CN103554981A (en) | Red reactive dye | |
| CN105440728A (en) | Red reactive dye and preparation method thereof | |
| CN102286216A (en) | Orange nylon active dyestuff and preparation method thereof | |
| CN105273437A (en) | Red reactive dye as well as preparation method and application thereof | |
| CN102876071A (en) | Red reactive dye and preparation method thereof | |
| CN103351645A (en) | Reactive blue dye and preparation method thereof | |
| CN101704770B (en) | Method for preparing purple reactive dye | |
| CN105504868A (en) | Red reactive dye | |
| CN102391684B (en) | A kind of Yellow active dye contaminating nylon and preparation method thereof | |
| CN101481522B (en) | Preparation of red reactive dye for fur | |
| CN102321387B (en) | A kind of nylon reactive yellow dye and preparation method thereof | |
| CN104277490A (en) | Reactive dye for nylon and preparation method of reactive dye | |
| CN101760041B (en) | Active navy blue dye | |
| CN101735657B (en) | Method for preparing active dye for purple wool | |
| CN101709044B (en) | Preparation method of purple active dye for wool | |
| CN102391671A (en) | Nylon orange reactive dye and preparation method thereof | |
| CN102504586A (en) | Blue reactive dye and its preparation method | |
| CN101585973B (en) | Method for synthesizing acid red R3G by utilizing phase transfer catalysts | |
| CN102391675A (en) | Azo reactive dye and preparation method thereof | |
| CN101735652B (en) | Red reactive dye and preparation method thereof | |
| CN101817997B (en) | Dye | |
| CN101481525B (en) | Preparation of reactive red GN dye for fur |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20140205 |