CN104031409B - A kind of active deep red look dye well its preparation method - Google Patents
A kind of active deep red look dye well its preparation method Download PDFInfo
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- CN104031409B CN104031409B CN201410269736.9A CN201410269736A CN104031409B CN 104031409 B CN104031409 B CN 104031409B CN 201410269736 A CN201410269736 A CN 201410269736A CN 104031409 B CN104031409 B CN 104031409B
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- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 35
- 239000000975 dye Substances 0.000 claims abstract description 34
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000008878 coupling Effects 0.000 claims abstract description 10
- 238000010168 coupling process Methods 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 10
- 239000012954 diazonium Substances 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 32
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 235000010288 sodium nitrite Nutrition 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 238000006277 sulfonation reaction Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- 238000010009 beating Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 23
- 229920000742 Cotton Polymers 0.000 abstract description 7
- 230000002708 enhancing effect Effects 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 229920002678 cellulose Polymers 0.000 abstract description 3
- 239000001913 cellulose Substances 0.000 abstract description 3
- 238000010018 discharge printing Methods 0.000 abstract description 3
- 238000007599 discharging Methods 0.000 abstract description 3
- 238000010186 staining Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 8
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010019 resist printing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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Abstract
The present invention is applicable to chemical dyestuff technical field, and provide a kind of active deep red look dye well its preparation method, described method comprises: a diazonium step: γ acid dissolve step: a Coupling step; Secondary diazonium step: secondary Coupling step.Pass through staining analysis, under equal conditions the more traditional activated red of product depth of the present invention exceeds 1.5 times, light fastness 5 grades, fastness to wet rubbing reach 4 grades, degree of fixation reaches 88%, enhancing rate is up to 10%, dyeing residual liquid is few, belongs to environmental protection and energy saving dyestuff, meets national energy-saving and reduces discharging policy.Product of the present invention, except for except traditional cellulose dyeing, is more suitable for continuous knot dyeing, discharge printing and brocade/cotton one-bath dyeing.
Description
Technical field
The invention belongs to chemical dyestuff technical field, particularly relate to a kind of active deep red look dye well its preparation method.
Background technology
Reactive dyestuffs also known as chemically-reactive dyes, for when dyeing and the dye of fiber react with.In this kind of dye molecule containing can with the group of fiber generation chemical reaction, during dyeing, dyestuff and fiber-reactive, form covalent linkage therebetween, becomes overall, and washable and fastness to rubbing is improved.Reactive dyestuffs are class new dyes.Owing to having economy, environmental protection, chromatogram is complete, suitability is wide etc., and proportion that advantage 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, the development of serious restriction reactive dyestuffs.Domestic BLENDED FABRIC one-bath one-step dyeing new dyeing technology obtains tremendous development recent years simultaneously, is widely used in dyeing, market is badly in need of the reactive dyestuffs being applicable to wash the fabric one-bath dyeing such as/cotton, brocade/cotton.
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 for the cooling of 2,5-dimethoxy para-ester and hydrochloric acid, sodium nitrite solution are carried out diazotization reaction and obtains a diazo liquid;
γ acid dissolve step: after γ acid making beating is dissolved, adjust pH value to be 7-9 with alkaline solution, obtain γ acid solution;
A Coupling step: a described diazo liquid and described γ acid solution are carried out being obtained by reacting a conjugates;
Secondary diazonium step: sulfonation para-ester and hydrochloric acid, sodium nitrite solution are carried out diazotization reaction and obtains secondary diazo liquid;
Secondary Coupling step: added in a described conjugates by described secondary diazo liquid and carry out being obtained by reacting secondary conjugates, filters after reacting completely, then carries out drying to filtrate and obtain the active deep red look dyestuff shown in formula I.
Preferably, the mol ratio of wherein said 2,5-dimethoxy para-esters, 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 containing multiple sulfonic acid group, when 50 DEG C, colorant dissolubility is at about 250g/L, and solvability is high.By staining analysis, under equal conditions the more traditional activated red of this product depth exceeds 1.5 times, and light fastness 5 grades, 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 for except traditional cellulose dyeing, is more suitable for continuous knot dyeing, discharge printing and brocade/cotton one-bath dyeing.
Accompanying drawing explanation
Fig. 1 is the schema of the active deep red look preparation of dyestuff method that the embodiment of the present invention provides.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearly understand, 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, be not intended to limit the present invention.
The invention provides active deep red look dyestuff and be mainly used in the dip-dye of cotton and cellulosic fibre, continuous knot dyeing, stamp and discharge printing, brocade/cotton one-bath dyeing can also be used for.Present invention also offers a kind of preparation method of active deep red look dyestuff, as shown in Figure 1, comprise the steps:
Step S101, a diazonium step.
Rear for the cooling of 2,5-dimethoxy para-ester and hydrochloric acid, sodium nitrite solution are carried out diazotization reaction and obtains a diazo liquid.
Step S102, γ acid dissolve step.
After γ acid making beating is dissolved, adjust pH value to be 7-9 with alkaline solution, obtain γ acid solution.
Step S103, a Coupling step.
A described diazo liquid and described γ acid solution are carried out being obtained by reacting a conjugates.
Step S104, secondary diazonium step.
Sulfonation para-ester and hydrochloric acid, sodium nitrite solution are carried out diazotization reaction and obtains secondary diazo liquid.
Step S105, secondary Coupling step.
Described secondary diazo liquid is added in a described conjugates and carries out being obtained by reacting secondary conjugates, filter after reacting completely, then drying is carried out to filtrate and obtain the active deep red look dyestuff shown in formula I;
In proportioning of selecting materials, the mol ratio of described 2,5-dimethoxy para-esters, γ acid, sulfonation para-ester is 1-1.1:0.95-1.1:1-1.1.
Preferably, in step S105, adopt spraying dry after Dyestuff synthesis, such quantity of wastewater effluent is few.
Can find out from formula I, containing multiple sulfonic acid group in this dye structure, solvability is high, can be widely used in cellulose dyeing, continuous knot dyeing and discharge, resist printing.In addition, containing 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 high by good, the solid rate look of active deep red look dyestuff depth that the inventive method is obtained, 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, dry fastness 5 grades, light fastness 5 grades, degree of fixation about 88%, enhancing rate is up to 10%.In addition, dawn is effective, the openpore aberration 4-5 level front with dye of the whiteness after discharge.
Below by several specific embodiment, be verified the Color of the active deep red look dyestuff that the inventive method obtains, the number that each embodiment Raw is selected is mass parts.
embodiment 1
1) at 341 part 2, add in 5-dimethoxy para-ester after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 69 parts again, maintain 3-7 DEG C of reaction and obtain a diazo liquid in 3 hours;
2) 239 parts of γ acid is pulled an oar when 15-20 DEG C within 1 hour, dissolve, then adjust pH value to be 7.0-7.5 with sodium hydroxide solution;
3) γ acid solution thread is slowly joined in a diazo liquid, adjust pH value to be 3.0 with sodium bicarbonate dry powder, within 6 hours, obtain a conjugates 0-5 DEG C of reaction;
4) 361 parts of sulfonation para-ester are added after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, then add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 69 parts, maintain 3-7 DEG C of reaction and obtain secondary diazo liquid in 3 hours;
5) described secondary diazo liquid is added in a conjugates, adjust pH value to be that 6.5-7.0 carries out reaction and obtains secondary conjugates in 8 hours with sodium bicarbonate, filter after reacting completely, then spraying dry is carried out to filtrate, finally pack to obtain finished product.
embodiment 2
1) at 341 part 2, add in 5-dimethoxy para-ester after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 69 parts again, maintain 3-7 DEG C of reaction and obtain a diazo liquid in 3 hours;
2) 227 parts of γ acid is pulled an oar when 15-20 DEG C within 1 hour, dissolve, then adjust pH value to be 8.0-8.5 with sodium hydroxide solution;
3) γ acid solution thread is slowly joined in a diazo liquid, adjust pH value to be 3.0 with sodium bicarbonate dry powder, within 8 hours, obtain a conjugates 0-5 DEG C of reaction;
4) 361 parts of sulfonation para-ester are added after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, then add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 69 parts, maintain 3-7 DEG C of reaction and obtain secondary diazo liquid in 3 hours;
5) described secondary diazo liquid is added in a conjugates, adjust pH value to be that 6.5-7.0 carries out reaction and obtains secondary conjugates in 8 hours with sodium bicarbonate, filter after reacting completely, then spraying dry is carried out to filtrate, finally pack to obtain finished product.
embodiment 3
1) at 375 part 2, add in 5-dimethoxy para-ester after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 76 parts again, maintain 3-7 DEG C of reaction and obtain a diazo liquid in 3 hours;
2) 239 parts of γ acid is pulled an oar when 15-20 DEG C within 1 hour, dissolve, then adjust pH value to be 8.5-9.0 with sodium hydroxide solution;
3) γ acid solution thread is slowly joined in a diazo liquid, adjust pH value to be 3.0 with sodium bicarbonate dry powder, within 8 hours, obtain a conjugates 0-5 DEG C of reaction;
4) 397 parts of sulfonation para-ester are added after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, then add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 76 parts, maintain 3-7 DEG C of reaction and obtain secondary diazo liquid in 3 hours;
5) described secondary diazo liquid is added in a conjugates, adjust pH value to be that 6.5-7.0 carries out reaction and obtains secondary conjugates in 6 hours with sodium bicarbonate, filter after reacting completely, then spraying dry is carried out to filtrate, finally pack to obtain finished product.
embodiment 4
1) at 341 part 2, add in 5-dimethoxy para-ester after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 69 parts again, maintain 3-7 DEG C of reaction and obtain a diazo liquid in 3 hours;
2) 239 parts of γ acid is pulled an oar when 15-20 DEG C within 1 hour, dissolve, then adjust pH value to be 7.0 with sodium hydroxide solution;
3) γ acid solution thread is slowly joined in a diazo liquid, adjust pH value to be 3.0 with sodium bicarbonate dry powder, within 6 hours, obtain a conjugates 0-5 DEG C of reaction;
4) 379 parts of sulfonation para-ester are added after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C, then add the Sodium Nitrite (being made into the solution that mass percent is 30%) of 76 parts, maintain 3-7 DEG C of reaction and obtain secondary diazo liquid in 3 hours;
5) described secondary diazo liquid is added in a conjugates, adjust pH value to be that 6.5-7.0 carries out reaction and obtains secondary conjugates in 8 hours with sodium bicarbonate, filter after reacting completely, then spraying dry is carried out to filtrate, finally pack to obtain finished product.
Carry out dyeing test to the active deep red look dyestuff that above-mentioned four embodiments are worth, test result is as shown in the table:
Can find out from upper table, under equal conditions the more traditional activated red of product depth of the present invention exceeds 1.5 times, and light fastness is 5 grades, fastness to wet rubbing reaches 4 grades, high, the degree of fixation of solubleness 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 done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within 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, comprise the steps:
A diazonium step: rear for the cooling of 2,5-dimethoxy para-ester and hydrochloric acid, sodium nitrite solution are carried out diazotization reaction and obtains a diazo liquid;
γ acid dissolve step: after γ acid making beating is dissolved, be 7-9 with alkaline solution adjust pH, obtain γ acid solution;
A Coupling step: a described diazo liquid and described γ acid solution are carried out being obtained by reacting a conjugates;
Secondary diazonium step: sulfonation para-ester and hydrochloric acid, sodium nitrite solution are carried out diazotization reaction and obtains secondary diazo liquid;
Secondary Coupling step: added in a described conjugates by described secondary diazo liquid and carry out being obtained by reacting secondary conjugates, filters after reacting completely, then carries out drying to filtrate and obtain the active deep red look dyestuff shown in formula I.
3. method as claimed in claim 2, is characterized in that, the mol ratio of wherein said 2,5-dimethoxy para-esters, γ acid, sulfonation para-ester is 1-1.1:0.95-1.1:1-1.1.
4. method as described in Claims 2 or 3, is characterized in that, a described diazonium step specifically comprises:
Add in 2,5-dimethoxy para-esters upon dissolution after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C;
Add sodium nitrite solution again and maintain 3-7 DEG C of reaction and within 3 hours, obtain a diazo liquid.
5. method as described in Claims 2 or 3, is characterized in that, in described γ acid dissolve step, alkaline solution used is sodium hydroxide solution, and γ acid beating time is 1 hour, making beating temperature is 15-20 DEG C.
6. method as described in Claims 2 or 3, is characterized in that, a described Coupling step specifically comprises:
Slowly being joined in a described diazo liquid by described γ acid solution thread, is 3.0 with sodium bicarbonate dry powder adjust pH, and reacts under 0-5 DEG C of condition and within 6-8 hour, obtain a conjugates.
7. method as described in Claims 2 or 3, is characterized in that, described secondary diazonium step specifically comprises:
Sulfonation para-ester is added after hydrochloric acid stirs 2 hours and be on the rocksly cooled to 0-5 DEG C;
Add sodium nitrite solution again and maintain 3-7 DEG C of reaction and obtain secondary diazo liquid in 3 hours.
8. method as described in Claims 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 carry out reaction and obtain secondary conjugates in 8 hours, filter after reacting completely;
Drying is carried out to filtrate and obtains the active deep red look dyestuff shown in formula I.
9. method as claimed in claim 8, is characterized in that, carry out spraying dry obtain the active deep red look dyestuff shown in formula I to filtrate.
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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 |
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2014
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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 |
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