CN103725036B - A kind of orange red active cationic dye - Google Patents
A kind of orange red active cationic dye Download PDFInfo
- Publication number
- CN103725036B CN103725036B CN201410002886.3A CN201410002886A CN103725036B CN 103725036 B CN103725036 B CN 103725036B CN 201410002886 A CN201410002886 A CN 201410002886A CN 103725036 B CN103725036 B CN 103725036B
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- CN
- China
- Prior art keywords
- dyeing
- orange red
- cationic dye
- compound
- active cationic
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Links
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 7
- 238000004043 dyeing Methods 0.000 abstract description 20
- 238000000034 method Methods 0.000 abstract description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract description 7
- 229960003512 nicotinic acid Drugs 0.000 abstract description 4
- 235000001968 nicotinic acid Nutrition 0.000 abstract description 4
- 239000011664 nicotinic acid Substances 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 230000007423 decrease Effects 0.000 abstract description 2
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 125000000627 niacin group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000009967 tasteless effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000835 fiber Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- -1 and then Substances 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NYUIWKRYVFSBMY-UHFFFAOYSA-N pyridine-3-carboxylic acid;triazine Chemical group C1=CN=NN=C1.OC(=O)C1=CC=CN=C1 NYUIWKRYVFSBMY-UHFFFAOYSA-N 0.000 description 1
- 238000004045 reactive dyeing Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
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Abstract
The invention discloses a kind of orange red active cationic dye, it has the structure as shown in figure (I).These reactive dyestuffs can to cellulose dyeing under salt-free, alkali-free condition, and reaction product is nicotinic acid, nontoxic, tasteless.This dyeing technique is simple, and formulation cost is low, and decreases the pollution to environment.
Description
Technical field
The present invention relates to active dye technical field, particularly relate to a kind of orange red active cationic dye.
Background technology
Traditional reactive dyestuffs in exhaustion technique mainly contains two steps: first, and under the short dye effect of salt, reactive dyestuffs are adsorbed onto on fiber, and then, dyestuff and fiber form covalent bonds under the effect of alkali.Use a large amount of salt and alkali in reactive dyeing, not only make dyeing complicated, cost increases, but also can cause serious ecological problem.Environmental problem comes into one's own day by day, and the environmental friendliness processing technology of textile printing and dyeing processing becomes the focus of now research, and wherein the salt-free dyeing of reactive dyestuffs and alkali-free fixation are one of research emphasis.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of reactive dyestuffs, can under salt-free conditions on fixation under dye and alkali-free condition, dyeing by product toxicological harmless, and easy to use, cost-saving, application performance excellence, is mainly used in the dyeing of cellulosic fibre.
In order to solve the problems of the technologies described above, the technical solution used in the present invention is: a kind of orange red active cationic dye, has structure as Suo Shi (I)
（Ⅰ）
Present invention also offers a kind of salt-free non-alkali dyeing method of cellulosic fibre, comprise the dyestuff and cellulosic fibre contact procedure that make formula I.
The reactive dyestuffs that the present invention produces, because its dye matrix is positively charged in aqueous, can with cotton fibre electronegative in water by charge attraction contaminate, without the need to the short dye of salt.Because containing nicotinic acid Triazine reactive group in dyestuff, this reactive group, under high temperature action, without the need to the effect of alkaline agent, can form covalent linkage with the hydroxyl reaction on cellulosic fibre.This dyeing process does not need to add other auxiliary agent, and dyeing is simple, and dyeing cost is low, and dyestuff has very high dye uptake and degree of fixation, and sewage discharge is few, is a kind of environmental protection type dye of applicable cleaner production.
Accompanying drawing explanation
Fig. 1 is the dyeing curve of the dyestuff cotton fibre of formula I.
Fig. 2 is that active dyestuff Kayacion Blue P-GR is to the dyeing curve of cotton fibre.
Fig. 3 is dyestuff and the cellulosic fibre reaction process schematic diagram of formula I.
Embodiment
The orange red active cationic dye structure of the present invention is illustrated above, below will the present invention is further illustrated by embodiment.
Embodiment 1:
This example provides the preparation method of formula I dyestuff, and the method comprises the steps:
The synthesis of A, compound (II)
（Ⅱ）
Under room temperature, added by 300mL acetone benzene in 500 mL there-necked flasks, rapid stirring also adds 11.2 g1-aminoanthraquinone, 12.9 g cyanuric chlorides successively.Reaction solution is by adding K
2cO
3solution keeps pH 5.5 – 6, and stirred at ambient temperature reacts 10 hours, filters, and with acetone and sherwood oil cleaning, vacuum drying under 60 ° of C, obtains khaki color reaction product 17.4g, productive rate 93.9%.
The synthesis of B, compound (III)
（Ⅲ）
By compound (II) 7.4g and N, N-dimethyl-1,3-propylene diamine 5mL is dissolved in 150mLDMF and reacts, and is warmed up to 65 ° of C, stirring and refluxing 3 hours, rotary evaporation obtains crude product, use dissolve with ethanol product, filter, rotary evaporation falls ethanol, obtain reddish brown compound (III) 8.1g, productive rate 92.3%.
The synthesis of C, compound (IV)
（Ⅳ）
Compound (III) 1.74g and 0.4mL monochloroethane is dissolved in 150mL dehydrated alcohol and reacts, temperature of reaction 50 ° of C, stirring and refluxing 5 hours, react complete, be cooled to room temperature, suction filtration, filtrate is underpressure distillation removing alcohol solvent in a rotary evaporator, with namely obtaining orange red compound (IV) 1.48g after acetone mix and blend, productive rate 74%.
The synthesis of D, compound (I)
Be dissolved in 10mL water by compound (IV) 1.48g and 0.44g nicotinic acid and react, reaction solution is by adding K
2cO
3solution keeps pH 6.5,90 ° of C stirring reactions 6 hours, in reaction solution, add NaCl1g, and compound (I) salt precipitation out, filters, vacuum drying under 60 ° of C.Obtain orange red compound (I) 1.24g, productive rate 65%.
Embodiment 2:
Present embodiments provide the dyeing process of formula I compound to cotton fabric:
Concrete dyeing process is as follows:
Compound (I) consumption 1.0% (o.w.f), bath raio 1:50, first cotton fabric and dye liquor stir the 15min that dyes under 40 ° of C, are then warmed up to 100 ° of C with the speed of 2 ° of C/min, insulation 60min.Then take out cotton fabric, washing, soap (2g/L soap flakes, 90 ° of C, 5min), and washing is dried, dye uptake 94.2%, degree of fixation 72.8%.Dyeing curve as shown in Figure 1,
Be compared to active dyestuff, the dyeing curve (Fig. 2) of such as Kayacion Blue P-GR, can find out that compound (I) can realize the salt-free non-alkali dyeing of reactive dyestuffs.
As shown in Figure 3, generate product nicotinic acid after reaction, nicotinic acid is a kind of water-soluble VITAMIN, toxicological harmless effect for the dyestuff of formula I and cellulosic fibre reaction process.
After compound (I) dyeing prepared by the present invention, colour fastness index is as follows:
Every colour fastness index after this dyeing visible is all very good, does not decline because of not adding salt and alkali in reaction process.
Claims (1)
1. an orange red active cationic dye, it has the structure as shown in formula I:
。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410002886.3A CN103725036B (en) | 2014-01-05 | 2014-01-05 | A kind of orange red active cationic dye |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410002886.3A CN103725036B (en) | 2014-01-05 | 2014-01-05 | A kind of orange red active cationic dye |
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| CN103725036A CN103725036A (en) | 2014-04-16 |
| CN103725036B true CN103725036B (en) | 2015-09-30 |
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| CN201410002886.3A Expired - Fee Related CN103725036B (en) | 2014-01-05 | 2014-01-05 | A kind of orange red active cationic dye |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105694529B (en) * | 2015-11-30 | 2017-06-23 | 南京工业大学 | Cationic reactive dye containing polyether amine chain segment and preparation method thereof |
| CN108795099A (en) * | 2018-03-30 | 2018-11-13 | 盐城工业职业技术学院 | A kind of cotton fluorescent dye |
| CN109575636A (en) * | 2018-12-16 | 2019-04-05 | 盐城工业职业技术学院 | A kind of reactive dye |
| CN109575639A (en) * | 2018-12-16 | 2019-04-05 | 盐城工业职业技术学院 | A kind of reactive dye |
| CN109651838A (en) * | 2018-12-16 | 2019-04-19 | 盐城工业职业技术学院 | A kind of reactive dye |
| CN109575638A (en) * | 2018-12-16 | 2019-04-05 | 盐城工业职业技术学院 | A kind of reactive dye |
| CN109651840A (en) * | 2018-12-16 | 2019-04-19 | 盐城工业职业技术学院 | A kind of reactive dye |
| CN110616575A (en) * | 2019-10-25 | 2019-12-27 | 万得化工科技(上海)有限公司 | Reactive dye for textile and environment-friendly salt-free dyeing process thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0418623A1 (en) * | 1989-09-16 | 1991-03-27 | Bayer Ag | Method of preparing reactive dyes |
| US5175259A (en) * | 1991-03-08 | 1992-12-29 | Basf Aktiengesellschaft | Mono- and bis-azo compounds containing 6-hydroxy-3-heterocyclic onium-pyridone-2-groupings coupled to diazo components containing diazine or triazine rings |
| CN1986647A (en) * | 2006-12-20 | 2007-06-27 | 东华大学 | Antiseptic active cationic dye and its preparing method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5930971A (en) * | 1982-07-06 | 1984-02-18 | 日本化薬株式会社 | Printing and padding dyeing of cellulose and cellulose containing fiber material |
| GB0411585D0 (en) * | 2004-05-24 | 2004-06-23 | Dystar Textilfarben Gmbh & Co | New reactive dyes |
-
2014
- 2014-01-05 CN CN201410002886.3A patent/CN103725036B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0418623A1 (en) * | 1989-09-16 | 1991-03-27 | Bayer Ag | Method of preparing reactive dyes |
| US5175259A (en) * | 1991-03-08 | 1992-12-29 | Basf Aktiengesellschaft | Mono- and bis-azo compounds containing 6-hydroxy-3-heterocyclic onium-pyridone-2-groupings coupled to diazo components containing diazine or triazine rings |
| CN1986647A (en) * | 2006-12-20 | 2007-06-27 | 东华大学 | Antiseptic active cationic dye and its preparing method |
Non-Patent Citations (1)
| Title |
|---|
| 《吡啶三嗪阳离子活性染料无盐无碱染色》;张伟 等;《印染》;20131231(第24期);10-12 * |
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| CN103725036A (en) | 2014-04-16 |
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Address after: 224000 No. 265 Jiefang South Road, Jiangsu, Yancheng City Applicant after: YANCHENG INSTITUTE OF INDUSTRY TECHNOLOGY Address before: 224000 No. 265 Jiefang South Road, Jiangsu, Yancheng City Applicant before: Yancheng Textile Vocational Technology College |
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Free format text: CORRECT: APPLICANT; FROM: YANCHENG TEXTILE VOCATIONAL TECHNOLOGY COLLEGE TO: YANCHENG INSTITUTE OF INDUSTRY TECHNOLOGY |
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Effective date of registration: 20171221 Address after: 224600 Jiangsu province Yancheng City town four village (Park) Patentee after: XIANGSHUI AITE TEXTILE Co.,Ltd. Address before: Chunhui Road Economic Development Zone Xishan District Jiangsu city of Wuxi province No. 155 214100 Patentee before: WUXI ZHIGENGNIAO NETWORK TECHNOLOGY CO.,LTD. Effective date of registration: 20171221 Address after: Chunhui Road Economic Development Zone Xishan District Jiangsu city of Wuxi province No. 155 214100 Patentee after: WUXI ZHIGENGNIAO NETWORK TECHNOLOGY CO.,LTD. Address before: 224000 No. 265 Jiefang South Road, Jiangsu, Yancheng City Patentee before: YANCHENG INSTITUTE OF INDUSTRY TECHNOLOGY |
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Granted publication date: 20150930 Termination date: 20180105 |