CN101418135A - Orange reactive dyes for wool and preparation method thereof - Google Patents
Orange reactive dyes for wool and preparation method thereof Download PDFInfo
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- CN101418135A CN101418135A CNA2008100542141A CN200810054214A CN101418135A CN 101418135 A CN101418135 A CN 101418135A CN A2008100542141 A CNA2008100542141 A CN A2008100542141A CN 200810054214 A CN200810054214 A CN 200810054214A CN 101418135 A CN101418135 A CN 101418135A
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Abstract
The invention relates to orange wool reactive dye and a preparation method thereof, which belong to the field of printing and dyeing. The orange wool reactive dye comprises the structural formula as above. Moreover, the invention also relates to the method for preparing the range reactive dye. Both the color fastness and the fixation rate of the orange reactive dye are superior to those of the orange reactive dye in the prior art. The orange wool reactive dye has high use value as being applied and examined, has high leveling property and dyeing degree and superior fastness performance indexes, and is particularly suitable for pad dyeing. Moreover, the preparation process and the mixture ratio of raw materials are reasonable; generation of miscellaneous and auxiliary dye is reduced; plasmogen spray drying is adopted; no process waste water is generated; and the orange wool reactive dye is favorable for environmental protection. Therefore, the dye has good applicability and environmental protection.
Description
Technical field
The present invention relates to active dye technical field, particularly relate to orange reactive dyes for wool and preparation method thereof.
Background technology
Reactive dyestuffs have lovely luster, application performance excellence, distinguishing feature such as easy to use.Along with ecotope is compeled, people's environmental consciousness is progressively strengthened, and dyestuff preparation and use reduce discharge of wastewater to greatest extent or reduce dyestuff content in the waste water and be beneficial to qualified discharge environment protection is required especially.Dyestuff on fabric the height of the every fastness index of chromogen then embodied the stability of this dyestuff, present most dyestuff dyeing course, on dye fastness dye uptake low, that especially pad dyeing is general＜75% and exist fastness ability good, dye then inhomogeneous, on dye evenly the then problem of fastness ability difference.
Summary of the invention
In view of the problem that the dyestuff of prior art exists, special the present invention proposed.
Therefore, the object of the present invention is to provide a kind of active orange dye, this dyestuff can either guarantee even dyeing, can guarantee colour fastness again.
Another object of the present invention is to provide a kind of preparation method of described active orange dye.
Structures shape character, the present invention makes it have less linear molecule by the rational molecular structure of design dyestuff, and good water solubility is beneficial to that diffusion also combines with fiber absorption in dye bath.
More particularly, the structural formula of active orange dye of the present invention is as follows:
Structural formula 1
In the formula:
R is C
1-C
6Alkyl, preferred C
2-C
4Alkyl, more preferably ethyl or propyl group are preferably ethyl.
M is a basic metal, is preferably sodium or potassium, more preferably sodium.
Preferably, M is a sodium in the described active orange dye structure, and R is an ethyl.At this moment, its molecular formula is C
24H
17N
6S
6O
18Na
5, molecular weight is 984.3.
Above-mentioned active orange dye structure can prepare with method known to a person of ordinary skill in the art, and diazotization, the coupling of promptly adopting those of ordinary skills to know prepares active orange dye structure of the present invention.Yet preferably, adopt method preparation of the present invention.
Preparation method of the present invention comprises:
1,2-naphthylamines-3,6,8-trisulfonic acid diazotization: Xiang Shuizhong add 2-naphthylamines-3,6, the making beating of 8-trisulfonic acid, cooling also adds sodium nitrite solution diazotization fast, then, temperature is controlled at 0～10 ℃ of stirring kept nitrous acid little excessive in 1.5～3 hours, then, remove excessive Sodium Nitrite with thionamic acid, obtain diazonium salt, in order to a step coupling.
2, step coupling a: Xiang Shuizhong add 2,4-diamino benzene sulfonic acid sodium, be stirred to moltenly entirely, add above-mentioned diazonium salts in 5～20 ℃ then and carry out coupled reaction, keep stirring, diazonium salt is disappeared be terminal point, churning time is generally 0.5～3 hour, and the coupling solution that is obtained is equipped with two step couplings.
3, (beta-sulfuric ester ethyl sulfonyl) aniline diazotization: Xiang Shuizhong is added (beta-sulfuric ester ethyl sulfonyl) aniline and dispersion, perhaps with basic solution, preferably with after the sodium carbonate solution dissolving, cooling and acidifying, add sodium nitrite solution then and keep the little excessive stirring of Sodium Nitrite 1.5～3 hours, remove excessive nitrous acid with thionamic acid then at 0～5 ℃.Acquisition is to (beta-sulfuric ester ethyl sulfonyl) diazonium salt of aniline, in order to two step couplings.
4, two step couplings: in 5～20 ℃, add in the coupling solution of step 2 that step 3 obtains to (beta-sulfuric ester ethyl sulfonyl) diazonium salt of aniline, and use mineral acid, preferably with the carbonic acid adjustment and kept PH=5.5～6 stirrings 1～2 hour.
5, spraying drying: with the dye solution of above-mentioned steps 4 preparation, deliver to after the filtration pack after the spray tower drying finished product.
Should be pointed out that as required active orange dye of the present invention is the drying in-field use not.Therefore, step 5 is preferred steps of preparation method of the present invention.
Preferably, the ice cube cooling is adopted in the cooling in the step 1.
In addition, acidifying can be adopted mineral acid in the step 3, as sulfuric acid; Organic acid is realized even, preferably adopts hydrochloric acid to carry out acidifying.And such change is conspicuous to those skilled in the art, so these changes all fall within protection scope of the present invention.
Similarly, the carbonic acid in the step 4 also can adopt organic acid to substitute, as long as can play and add identical that carbonic acid plays a part.Yellow soda ash in the step 3 can adopt other strong base-weak acid salt to substitute.And such change is conspicuous to those skilled in the art, and therefore, these changes all fall within protection scope of the present invention.
In the present invention, as shown in the table for preparing raw material and consumption that described active orange dye adopts:
| Material name | Molecular weight | Content (%) | Consumption (kg) | Remarks |
| 2-naphthylamines-3,6,8-trisulfonic acid | 383.3 | 73.0 | 510～530 | |
| 2,4-diamino benzene sulfonic acid sodium | 210.0 | 98.0 | 200～220 |
| To (beta-sulfuric ester ethyl sulfonyl) aniline | 281 | 96.0 | 290～305 | |
| Sodium Nitrite | 69 | 96.0 | 140～150 | |
| Hydrochloric acid | 31.5 | 30.0 | 190～310 | |
| Yellow soda ash | Consumption is as the criterion with PH | |||
| Thionamic acid |
Embodiment 1
1. 2-naphthylamines-3,6,8-trisulfonic acid diazotization: in 1000kg water, add content and be 73% 2-naphthylamines-3,6,8-trisulfonic acid 525.1kg and stir, adding trash ice 600kg temperature then is 0 ℃, the sodium nitrite solution 278.8kg of quick adding 25%, adding the back keeps Sodium Nitrite little excessive, stirred 2 hours, this moment, temperature was 5 ℃, removed excessive Sodium Nitrite with thionamic acid.Be equipped with coupling.
2. a step coupling: in 700kg water, add content and be 98% 2,4-diamino benzene sulfonic acid sodium 214.3kg, it is molten entirely to stir after 30 minutes material, this moment, temperature was 30 ℃, added the diazonium salt that 1. step prepares then fast, kept 20 ℃ of 1 hour temperature of stirring.Be equipped with two step couplings.
3. to (beta-sulfuric ester ethyl sulfonyl) aniline diazotization: in 1000kg water, add content and be 96% (beta-sulfuric ester ethyl sulfonyl) aniline 301.5kg is stirred add trash ice 600kg after 1 hour, add 30% hydrochloric acid 200kg then, this moment, temperature was 0 ℃, the sodium nitrite solution 285kg of adding 25% adds the little excessive stirring of back maintenance Sodium Nitrite 2 hours fast, this moment, temperature was 5 ℃, removed excessive Sodium Nitrite with thionamic acid then.Be equipped with two step couplings.
4. two step couplings: will join in the step solution 2. to (beta-sulfuric ester ethyl sulfonyl) diazonium salt of aniline, adding the back temperature is 15 ℃, and the sodium carbonate solution with 20% was with 0.5 hour adjustment PH=5.5, keep PH=5.5～6 then and stirred 1 hour, this moment, temperature was 18 ℃.
5. spraying drying: deliver to after the dye solution that 4. step is prepared filters after the spray tower drying dry product 1300kg.
Embodiment 2
1. 2-naphthylamines-3,6, the 8-trisulfonic acid 514.6kg of adding 73% stir in 1000kg water, adding trash ice 600kg temperature then is 0 ℃, the sodium nitrite solution 273.2kg of quick adding 25%, adding the back keeps Sodium Nitrite little excessive, stirred 2 hours, this moment, temperature was 5 ℃, removed excessive Sodium Nitrite with thionamic acid.Be equipped with coupling.
2. 3. 4. with example 1.
5. get dry product 1280kg.
Embodiment 3
1. with example 1.
2. in 500kg water, add content and be 98% 2,4-diamino benzene sulfonic acid sodium 214.3kg stirs after 1 hour, is cooled to 5 ℃ with trash ice 300kg, adds the diazonium salt that 1. step prepares then fast, keeps stirring 2 hours, temperature is 10 ℃ at this moment.Be equipped with two step couplings.
3. 4. 5. with example 1, get dry product 1300kg after the drying.
Embodiment 4
1. 2. with example 1.
3. to (beta-sulfuric ester ethyl sulfonyl) aniline diazotization: in 1000kg water, add content and be 96% to (beta-sulfuric ester ethyl sulfonyl) aniline 292.7kg, other are with example 1.
4. with example 1.
5. get dry product 1290kg.
Embodiment 5
1. 2. with example 1.
3. in 800kg water, add (beta-sulfuric ester ethyl sulfonyl) aniline (96%) 296kg, being neutralized to PH=4.5 with 20% sodium carbonate solution then dissolves substantially to (beta-sulfuric ester ethyl sulfonyl) aniline, add trash ice 600kg then, add 30% hydrochloric acid 286kg, this moment, temperature was 0 ℃, add 25% sodium nitrite solution 279kg then, stir after 1 hour 4 ℃ of temperature, remove excessive Sodium Nitrite with thionamic acid.Be equipped with two step couplings.
4. with example 1.
5. get dry product 1335kg.
Active orange dye of the present invention and prior art active orange dye have been listed below, as the performance comparison table of reactive orange 3R
Pad dyeing fixation Shuai ≧ 85% of active orange dye of the present invention
Reactive dyestuffs common product degree of fixation about 75% of the prior art
As can be seen from the above table, no matter active orange dye of the present invention still is the active orange dye that degree of fixation all is better than prior art at colour fastness.
Structure dyestuff of the present invention possesses very high practical value through application verification.Preparation process, reasonable raw material proportioning have reduced the generation of assorted secondary dye well inorganic salt, the magma spraying drying, and no processing wastewater is beneficial to environmental protection.
In addition, active orange dye of the present invention has the level-dyeing property of height, is particularly useful for pad dyeing and dye uptake is higher, and every fastness ability index is superior and preparation process technology is easy, does not produce waste water, so dyestuff of the present invention possesses the favorable applicability and the feature of environmental protection.
Active orange dye of the present invention and preparation method thereof, those skilled in the art can in not breaking away from content of the present invention, spirit and scope, can make improvements or change by using for reference this paper content to raw material, processing parameter, processing step etc.And these changes and change apparent to those skilled in the artly all fall within protection scope of the present invention.Protection scope of the present invention is determined by appending claims and equivalent thereof.
Claims (12)
1, a kind of active orange dye, its structure is:
In the formula: R represents C
1-C
6Alkyl, M represents basic metal.
2, dyestuff according to claim 1, wherein, R represents C
2-C
4Alkyl, M represents sodium or potassium.
3, dyestuff according to claim 1 and 2, wherein, R represents ethyl or propyl group.
4, dyestuff according to claim 3, wherein, R is an ethyl.
5, according to the described dyestuff of one of claim 1-4, wherein M is a sodium.
6, a kind of method for preparing one of claim 1-5 described dyestuff comprises the steps:
1,2-naphthylamines-3,6,8-trisulfonic acid diazotization: Xiang Shuizhong add 2-naphthylamines-3,6, the making beating of 8-trisulfonic acid, cooling also adds sodium nitrite solution diazotization fast, then, temperature is controlled at 0～10 ℃ of stirring kept nitrous acid little excessive in 1.5～3 hours, then, remove excessive Sodium Nitrite with thionamic acid, obtain diazonium salt, in order to a step coupling;
2, step coupling a: Xiang Shuizhong add 2,4-diamino benzene sulfonic acid sodium, be stirred to moltenly entirely, add above-mentioned diazonium salts in 5～20 ℃ then and carry out coupled reaction, keep stirring, diazonium salt is disappeared be terminal point, churning time is generally 0.5～3 hour, and the coupling solution that is obtained is equipped with two step couplings;
3, (beta-sulfuric ester ethyl sulfonyl) aniline diazotization: Xiang Shuizhong is added (beta-sulfuric ester ethyl sulfonyl) aniline and dispersion, perhaps with after the basic solution dissolving, cooling and acidifying, add sodium nitrite solution then and keep the little excessive stirring of Sodium Nitrite 1.5～3 hours at 0～5 ℃, remove excessive nitrous acid with thionamic acid then, acquisition is to (beta-sulfuric ester ethyl sulfonyl) diazonium salt of aniline, in order to two step couplings;
4, two step couplings: in 5～20 ℃, add in the coupling solution of step 2 that step 3 obtains to (beta-sulfuric ester ethyl sulfonyl) diazonium salt of aniline, and with the mineral acid adjustment and keep PH=5.5～6 and stirred 1～2 hour.
7, method according to claim 6 also comprises the steps:
Spraying drying: deliver to the spray tower drying after the dye solution filtration with claim 6 preparation, obtain the exsiccant dye product.
8, according to claim 6 or 7 described methods, wherein, the trash ice cooling is adopted in described cooling.
9, according to the described method of one of claim 6-8, wherein, the acidifying in the step 3 adopts mineral acid to realize.
10, method according to claim 9, described mineral acid are hydrochloric acid.
11, according to the described method of one of claim 6-10, wherein, the mineral acid in the step 4 is a carbonic acid.
12, according to the described method of one of claim 6-11, wherein, the basic solution in the step 3 is a sodium carbonate solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100542141A CN101418135A (en) | 2008-08-22 | 2008-08-22 | Orange reactive dyes for wool and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100542141A CN101418135A (en) | 2008-08-22 | 2008-08-22 | Orange reactive dyes for wool and preparation method thereof |
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|---|---|
| CN101418135A true CN101418135A (en) | 2009-04-29 |
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ID=40629144
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|---|---|---|---|
| CNA2008100542141A Pending CN101418135A (en) | 2008-08-22 | 2008-08-22 | Orange reactive dyes for wool and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103031004A (en) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | Reactive blue dye and its preparation method |
| CN103031003A (en) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | Deepest-color reactive dye |
| CN104119692A (en) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | Orange reactive dye compound and application thereof |
| CN104119694A (en) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | Orange reactive dye compound and application |
-
2008
- 2008-08-22 CN CNA2008100542141A patent/CN101418135A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103031004A (en) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | Reactive blue dye and its preparation method |
| CN103031003A (en) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | Deepest-color reactive dye |
| CN103031004B (en) * | 2010-08-27 | 2015-07-15 | 天津德凯化工股份有限公司 | Reactive blue dye and its preparation method |
| CN104119692A (en) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | Orange reactive dye compound and application thereof |
| CN104119694A (en) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | Orange reactive dye compound and application |
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Application publication date: 20090429 |