CN104031409A - Active crimson dye and preparation method thereof - Google Patents
Active crimson dye and preparation method thereof Download PDFInfo
- Publication number
- CN104031409A CN104031409A CN201410269736.9A CN201410269736A CN104031409A CN 104031409 A CN104031409 A CN 104031409A CN 201410269736 A CN201410269736 A CN 201410269736A CN 104031409 A CN104031409 A CN 104031409A
- Authority
- CN
- China
- Prior art keywords
- active
- dye
- acid
- diazo liquid
- conjugates
- 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.)
- Granted
Links
- 0 COc(cc1*C=Nc2cc3cc(*)c(CCC=Nc4ccc(*)cc4*)c(O)c3cc2N)c(*)cc1OC Chemical compound COc(cc1*C=Nc2cc3cc(*)c(CCC=Nc4ccc(*)cc4*)c(O)c3cc2N)c(*)cc1OC 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
The invention is applicable to the technical field of chemical dyes, and provides an active crimson dye and a preparation method thereof. The method comprises the steps of primary diazotizing, gamma acid dissolution, primary coupling, secondary diazotizing, and secondary coupling. Through dyeing analysis, the pile-on property of the active crimson dye disclosed by the invention is 1.5 times higher than that of a traditional active red dye under same conditions, the light fastness of the active crimson dye is grade 5, the fastness of the active crimson dye to wet rubbing reaches grade 4, the fixation rate of the active crimson dye reaches 88%, the upgrade rate of the active crimson dye is as high as 10%, and residual dyeing liquid is less, therefore, the active crimson dye belongs to an environmental-friendly and energy-saving dye, and accords with national policies for energy conservation and emissions reduction. The active crimson dye, disclosed by the invention, besides being applied to traditional cellulose fiber dyeing, is more applicable to continuous pad dyeing and discharge printing and the one-bath-process dyeing for brocades/cottons.
Description
Technical field
The invention belongs to chemical dyestuff technical field, relate in particular to a kind of active deep red look dye well its preparation method.
Background technology
Reactive dyestuffs claim again chemically-reactive dyes, are the dye at when dyeing and fiber react with.In this class dye molecule, contain can with the group of fiber generation chemical reaction, dyestuff and fiber-reactive when dyeing, form covalent linkage between the two, become entirety, and washable and fastness to rubbing is improved.Reactive dyestuffs are class new dyes.Because the proportion that the advantage such as have economy, environmental protection, chromatogram is complete, suitability is wide accounts in dyeing is increasing.
But reactive dyestuffs compare that other dye fixing rate is low, and utilization ratio is not high, and depth product is few, seriously restricts the development of reactive dyestuffs.Domestic BLENDED FABRIC one of while is bathed single stage method dyeing new technology and is obtained tremendous development recent years, has been widely used in dyeing, is badly in need of being applicable to the reactive dyestuffs of wash/cotton, bright and beautiful/fabric one-bath dyeings such as cotton on market.
Summary of the invention
In view of the above problems, the object of the present invention is to provide a kind of active deep red look dye well its preparation method, be intended to solve existing dark red reactive dye color fixing rate low, utilization ratio is not high, the technical problem that depth is not high.
On the one hand, described active deep red look dyestuff, its molecular structural formula is as shown in formula I:
On the other hand, described active deep red look preparation of dyestuff method comprises:
A diazonium step: rear the cooling of 2,5-dimethoxy para-ester and hydrochloric acid, sodium nitrite solution are carried out to diazotization reaction and obtain diazo liquid one time;
γ acid dissolving step: after γ acid making beating is dissolved, adjusting pH value with alkaline solution is 7-9, obtains γ acid solution;
A coupling step: a described diazo liquid is reacted and obtains conjugates one time with described γ acid solution;
Secondary diazonium step: sulfonation para-ester and hydrochloric acid, sodium nitrite solution are carried out to diazotization reaction and obtain secondary diazo liquid;
Secondary coupling step: described secondary diazo liquid is added in a described conjugates and reacts and obtain secondary conjugates, filter after reacting completely, then filtrate is dried and obtains the active deep red look dyestuff shown in formula I.
Preferably, wherein said 2, the mol ratio of 5-dimethoxy para-ester, γ acid, sulfonation para-ester is 1-1.1:0.95-1.1:1-1.1.
The invention has the beneficial effects as follows: in the present invention, active deep red look dyestuff contains two ethene sulfuryl active groups, and depth is good, and contains multiple sulfonic acid groups, 50 DEG C time, colorant dissolubility is in 250g/L left and right, and solvability is high.By staining analysis, under equal conditions the more traditional active red dye of this product depth exceeds 1.5 times, and 5 grades of light fastnesss, fastness to wet rubbing reach 4 grades, degree of fixation reaches 88%, and enhancing rate is up to 10%, and dyeing residual liquid is few, belong to environmental protection and energy saving dyestuff, meet national energy-saving and reduce discharging policy.This product, except the cellulose dyeing for traditional, is more suitable for continuous knot dyeing, discharge printing and brocade/cotton one-bath dyeing.
Brief description of the drawings
Fig. 1 is the schema of the active deep red look preparation of dyestuff method that provides of the embodiment of the present invention.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearer, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein, only in order to explain the present invention, is not intended to limit the present invention.
The invention provides dip-dye, continuous knot dyeing, stamp and discharge printing that active deep red look dyestuff is mainly used in cotton and cellulosic fibre, can also be used for brocade/cotton one-bath dyeing.The present invention also provides a kind of preparation method of active deep red look dyestuff, as shown in Figure 1, comprises the steps:
Step S101, a diazonium step.
Rear the cooling of 2,5-dimethoxy para-ester and hydrochloric acid, sodium nitrite solution are carried out to diazotization reaction and obtain diazo liquid one time.
Step S102, γ acid dissolving step.
After γ acid making beating is dissolved, adjusting pH value with alkaline solution is 7-9, obtains γ acid solution.
Step S103, a coupling step.
A described diazo liquid is reacted and obtains conjugates one time with described γ acid solution.
Step S104, secondary diazonium step.
Sulfonation para-ester and hydrochloric acid, sodium nitrite solution are carried out to diazotization reaction and obtain secondary diazo liquid.
Step S105, secondary coupling step.
Described secondary diazo liquid is added in a described conjugates and reacts and obtain secondary conjugates, after reacting completely, filter, then filtrate is dried and obtains the active deep red look dyestuff shown in formula I;
Aspect the proportioning of selecting materials, described 2, the mol ratio of 5-dimethoxy para-ester, γ acid, sulfonation para-ester is 1-1.1:0.95-1.1:1-1.1.
Preferably, in step S105, after dyestuff is synthetic, adopt spraying dry, quantity of wastewater effluent is few like this.
From formula I, can find out, in this dye structure, contain multiple sulfonic acid groups, solvability is high, can be widely used in cellulose dyeing, continuous knot dyeing and discharge, resist printing.In addition, contain two ethene sulfuryl active groups in this dye structure, depth is good, with low cost, and the application performances such as light fastness, washing fastness, fastness to wet rubbing are improved, and are also applicable to bright and beautiful cotton One Bath Dyeing Process.
The present invention is by selecting suitable raw material, and corresponding preparation technology is set, make that good, the solid rate look of the active deep red look dyestuff depth that makes by the inventive method is high, dyeing residual liquid is few, can alleviate dyeing environmental protection pressure, meet national energy-saving and reduce discharging policy; And fastness to wet rubbing is at 4 grades, 5 grades of dry fastnesses, 5 grades of light fastnesss, degree of fixation 88% left and right, enhancing rate is up to 10%.In addition, dawn is effective, the whiteness after discharge with dye front openpore aberration 4-5 level.
Below by several specific embodiments, be verified the Color of the active deep red look dyestuff that the inventive method makes, the umber that each embodiment Raw is selected is mass parts.
embodiment 1
1) at 341 part 2, in 5-dimethoxy para-ester, add hydrochloric acid to stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, add again the Sodium Nitrite (be made into mass percent be 30% solution) of 69 parts, maintain 3-7 DEG C of reaction 3 hours a diazo liquid;
2) 239 parts of γ acid are pulled an oar 15-20 DEG C time and dissolved for 1 hour, then to adjust pH value with sodium hydroxide solution be 7.0-7.5;
3) γ acid solution thread is slowly joined in a diazo liquid, adjusting pH value with sodium bicarbonate dry powder is 3.0, within 6 hours, obtains conjugates one time 0-5 DEG C of reaction;
4) 361 parts of sulfonation para-ester are added hydrochloric acid stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, then add the Sodium Nitrite (be made into mass percent be 30% solution) of 69 parts, maintain 3-7 DEG C of reaction and within 3 hours, obtain secondary diazo liquid;
5) described secondary diazo liquid is added in a conjugates, adjusting pH value with sodium bicarbonate is that 6.5-7.0 reacts and obtains secondary conjugates in 8 hours, filters, then filtrate spray and is dried after reacting completely, and finally packs to obtain finished product.
embodiment 2
1) at 341 part 2, in 5-dimethoxy para-ester, add hydrochloric acid to stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, add again the Sodium Nitrite (be made into mass percent be 30% solution) of 69 parts, maintain 3-7 DEG C of reaction 3 hours a diazo liquid;
2) 227 parts of γ acid are pulled an oar 15-20 DEG C time and dissolved for 1 hour, then to adjust pH value with sodium hydroxide solution be 8.0-8.5;
3) γ acid solution thread is slowly joined in a diazo liquid, adjusting pH value with sodium bicarbonate dry powder is 3.0, within 8 hours, obtains conjugates one time 0-5 DEG C of reaction;
4) 361 parts of sulfonation para-ester are added hydrochloric acid stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, then add the Sodium Nitrite (be made into mass percent be 30% solution) of 69 parts, maintain 3-7 DEG C of reaction and within 3 hours, obtain secondary diazo liquid;
5) described secondary diazo liquid is added in a conjugates, adjusting pH value with sodium bicarbonate is that 6.5-7.0 reacts and obtains secondary conjugates in 8 hours, filters, then filtrate spray and is dried after reacting completely, and finally packs to obtain finished product.
embodiment 3
1) at 375 part 2, in 5-dimethoxy para-ester, add hydrochloric acid to stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, add again the Sodium Nitrite (be made into mass percent be 30% solution) of 76 parts, maintain 3-7 DEG C of reaction 3 hours a diazo liquid;
2) 239 parts of γ acid are pulled an oar 15-20 DEG C time and dissolved for 1 hour, then to adjust pH value with sodium hydroxide solution be 8.5-9.0;
3) γ acid solution thread is slowly joined in a diazo liquid, adjusting pH value with sodium bicarbonate dry powder is 3.0, within 8 hours, obtains conjugates one time 0-5 DEG C of reaction;
4) 397 parts of sulfonation para-ester are added hydrochloric acid stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, then add the Sodium Nitrite (be made into mass percent be 30% solution) of 76 parts, maintain 3-7 DEG C of reaction and within 3 hours, obtain secondary diazo liquid;
5) described secondary diazo liquid is added in a conjugates, adjusting pH value with sodium bicarbonate is that 6.5-7.0 reacts and obtains secondary conjugates in 6 hours, filters, then filtrate spray and is dried after reacting completely, and finally packs to obtain finished product.
embodiment 4
1) at 341 part 2, in 5-dimethoxy para-ester, add hydrochloric acid to stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, add again the Sodium Nitrite (be made into mass percent be 30% solution) of 69 parts, maintain 3-7 DEG C of reaction 3 hours a diazo liquid;
2) 239 parts of γ acid are pulled an oar 15-20 DEG C time and dissolved for 1 hour, then to adjust pH value with sodium hydroxide solution be 7.0;
3) γ acid solution thread is slowly joined in a diazo liquid, adjusting pH value with sodium bicarbonate dry powder is 3.0, within 6 hours, obtains conjugates one time 0-5 DEG C of reaction;
4) 379 parts of sulfonation para-ester are added hydrochloric acid stir the 0-5 of being cooled to DEG C on the rocks after 2 hours, then add the Sodium Nitrite (be made into mass percent be 30% solution) of 76 parts, maintain 3-7 DEG C of reaction and within 3 hours, obtain secondary diazo liquid;
5) described secondary diazo liquid is added in a conjugates, adjusting pH value with sodium bicarbonate is that 6.5-7.0 reacts and obtains secondary conjugates in 8 hours, filters, then filtrate spray and is dried after reacting completely, and finally packs to obtain finished product.
The active deep red look dyestuff that above-mentioned four embodiment the are worth test of dyeing, test result is as shown in the table:
Can find out from upper table, under equal conditions the more traditional active red dye of product depth of the present invention exceeds 1.5 times, and light fastness is that 5 grades, fastness to wet rubbing reach that 4 grades, solubleness are high, degree of fixation reaches 88%, and enhancing rate is up to 10%.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all any amendments of doing within the spirit and principles in the present invention, be equal to and replace and improvement etc., within all should being included in protection scope of the present invention.
Claims (9)
1. an active deep red look dyestuff, its molecular structural formula is as shown in formula I:
2. the preparation method of active deep red look dyestuff as claimed in claim 1, is characterized in that, comprises the steps:
A diazonium step: rear the cooling of 2,5-dimethoxy para-ester and hydrochloric acid, sodium nitrite solution are carried out to diazotization reaction and obtain diazo liquid one time;
γ acid dissolving step: after γ acid making beating is dissolved, adjusting pH value with alkaline solution is 7-9, obtains γ acid solution;
A coupling step: a described diazo liquid is reacted and obtains conjugates one time with described γ acid solution;
Secondary diazonium step: sulfonation para-ester and hydrochloric acid, sodium nitrite solution are carried out to diazotization reaction and obtain secondary diazo liquid;
Secondary coupling step: described secondary diazo liquid is added in a described conjugates and reacts and obtain secondary conjugates, filter after reacting completely, then filtrate is dried and obtains the active deep red look dyestuff shown in formula I.
3. method as claimed in claim 2, is characterized in that, wherein said 2, and the mol ratio of 5-dimethoxy para-ester, γ acid, sulfonation para-ester is 1-1.1:0.95-1.1:1-1.1.
4. method as described in claim 2 or 3, is characterized in that, a described diazonium step specifically comprises:
After dissolving 2, in 5-dimethoxy para-ester, add hydrochloric acid to stir the 0-5 of being cooled to DEG C on the rocks after 2 hours;
Add again sodium nitrite solution and maintain 3-7 DEG C of reaction and within 3 hours, obtain diazo liquid one time.
5. method as described in claim 2 or 3, is characterized in that, in described γ acid dissolving step, alkaline solution used is sodium hydroxide solution, and γ acid beating time is that 1 hour, making beating temperature are 15-20 DEG C.
6. method as described in claim 2 or 3, is characterized in that, a described coupling step specifically comprises:
Described γ acid solution thread is slowly joined in a described diazo liquid, and adjusting pH value with sodium bicarbonate dry powder is 3.0, and under 0-5 DEG C of condition, reacts and within 6-8 hour, obtain conjugates one time.
7. method as described in claim 2 or 3, is characterized in that, described secondary diazonium step specifically comprises:
Add hydrochloric acid to stir the 0-5 of being cooled to DEG C on the rocks after 2 hours sulfonation para-ester;
Add again sodium nitrite solution and maintain 3-7 DEG C of reaction and within 3 hours, obtain secondary diazo liquid.
8. method as described in claim 2 or 3, is characterized in that, described secondary coupling step specifically comprises:
Described secondary diazo liquid is added in a described conjugates, with sodium bicarbonate adjust PH most 6.5-7.0 react and obtain secondary conjugates in 8 hours, after reacting completely, filter;
Filtrate is dried and obtains the active deep red look dyestuff shown in formula I.
9. method as claimed in claim 8, is characterized in that, to the filtrate dry active deep red look dyestuff shown in formula I that obtains of spraying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410269736.9A CN104031409B (en) | 2014-06-16 | 2014-06-16 | A kind of active deep red look dye well its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410269736.9A CN104031409B (en) | 2014-06-16 | 2014-06-16 | A kind of active deep red look dye well its preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104031409A true CN104031409A (en) | 2014-09-10 |
| CN104031409B CN104031409B (en) | 2016-01-20 |
Family
ID=51462416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410269736.9A Active CN104031409B (en) | 2014-06-16 | 2014-06-16 | A kind of active deep red look dye well its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104031409B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109504125A (en) * | 2018-10-31 | 2019-03-22 | 湖北华丽染料工业有限公司 | A kind of compound crimson active dyestuff suitable for low temperature dyeing |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855411A (en) * | 1988-03-17 | 1989-08-08 | Hugh C. Crall | Water-soluble, monoazo dyes containing a ureido group and two sulfonyl fiber-reactive groups |
| CN1594445A (en) * | 2003-08-16 | 2005-03-16 | 德意志戴斯达纺织品及染料两合公司 | Dye mixtures of fiber-reactive azo dyes, their preparation and their use |
| CN101580649A (en) * | 2009-06-11 | 2009-11-18 | 湖北华丽染料工业有限公司 | Composite active black dye |
| CN102199365A (en) * | 2011-03-25 | 2011-09-28 | 安徽省凤阳染料化工有限公司 | NK-BB red dye special for nylon, and preparation method thereof |
-
2014
- 2014-06-16 CN CN201410269736.9A patent/CN104031409B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855411A (en) * | 1988-03-17 | 1989-08-08 | Hugh C. Crall | Water-soluble, monoazo dyes containing a ureido group and two sulfonyl fiber-reactive groups |
| CN1594445A (en) * | 2003-08-16 | 2005-03-16 | 德意志戴斯达纺织品及染料两合公司 | Dye mixtures of fiber-reactive azo dyes, their preparation and their use |
| CN101580649A (en) * | 2009-06-11 | 2009-11-18 | 湖北华丽染料工业有限公司 | Composite active black dye |
| CN102199365A (en) * | 2011-03-25 | 2011-09-28 | 安徽省凤阳染料化工有限公司 | NK-BB red dye special for nylon, and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109504125A (en) * | 2018-10-31 | 2019-03-22 | 湖北华丽染料工业有限公司 | A kind of compound crimson active dyestuff suitable for low temperature dyeing |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104031409B (en) | 2016-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103073917B (en) | Black reactive dye composition | |
| CN101735649B (en) | Yellow to red composite reactive dye | |
| CN104059387A (en) | Compound black reactive dye composition, and applications thereof and fiber or fiber textile made thereby | |
| CN104059000B (en) | A kind of reactive dyestuffs and its production and use | |
| CN103013175A (en) | Reactive dye mixture and applications thereof | |
| CN100528972C (en) | Composite active dye | |
| CN100362055C (en) | Composite reactive yellow dye | |
| CN105176133A (en) | Cross-linkable active disperse dye compound, preparation and applications thereof | |
| CN110938039A (en) | Purple reactive dye based on trisazo multichromosome and preparation and application thereof | |
| CN106833012B (en) | A kind of Yellow reactive dyes and its preparation and application | |
| CN103013176B (en) | High-performance green reactive dye mixture and application thereof | |
| CN101555361B (en) | Active red dye composition | |
| CN101092522A (en) | Activated dye, prepartion method, and application | |
| CN104016880B (en) | The presoma of special azo reactive disperse dyes and purposes | |
| CN104031409B (en) | A kind of active deep red look dye well its preparation method | |
| CN105199427B (en) | A kind of polyazo reactive dye compound and preparation method thereof | |
| CN101143970B (en) | Dye compound and its preparation method and application | |
| CN106590013B (en) | The isomer mixture of CLT acid prepares acid dyes original powder and product | |
| CN109796786B (en) | Composite bright red reactive dye and preparation method and application thereof | |
| CN109021614B (en) | Phthalocyanine azo-based double-chromophore reactive dye with high fixation rate and preparation method and application thereof | |
| CN100494289C (en) | Navy blue quaternary ammonium salt bisazo chemically-reactive dyes | |
| CN103992659A (en) | Black reactive dye composition | |
| CN102702779A (en) | Red reactive dye and preparation as well as use thereof | |
| CN110903679A (en) | Green reactive dye based on monoazo structure of mono H acid and preparation and application thereof | |
| CN104403348A (en) | Purple disperse dye with high washing fastness and sublimation fastness and preparation method of purple disperse dye |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |