CN101705019B - Red reactive dye for wool and preparation method thereof - Google Patents
Red reactive dye for wool and preparation method thereof Download PDFInfo
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- CN101705019B CN101705019B CN 200910228596 CN200910228596A CN101705019B CN 101705019 B CN101705019 B CN 101705019B CN 200910228596 CN200910228596 CN 200910228596 CN 200910228596 A CN200910228596 A CN 200910228596A CN 101705019 B CN101705019 B CN 101705019B
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- 210000002268 wool Anatomy 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000985 reactive dye Substances 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000000975 dye Substances 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 62
- 239000007788 liquid Substances 0.000 claims description 33
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 238000005859 coupling reaction Methods 0.000 claims description 19
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- 239000012954 diazonium Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- -1 bromo propionyl chloros Chemical compound 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 238000006193 diazotization reaction Methods 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 7
- 208000006278 hypochromic anemia Diseases 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 238000005352 clarification Methods 0.000 claims description 5
- 235000017550 sodium carbonate Nutrition 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- KRRUJXFCUPBUCQ-UHFFFAOYSA-N 1,3,2,4-dioxadithietane 2,2,4,4-tetraoxide Chemical compound S1(=O)(=O)OS(=O)(=O)O1 KRRUJXFCUPBUCQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004218 Orcein Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 210000000085 cashmere Anatomy 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 235000019248 orcein Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention relates to a red reactive dye for wool and a preparation method thereof, the red reactive dye for wool is a compound with a structure shown in a general formula , the use and the preparation of the dye can reduce environmental pollution, the cost of required raw materials is low, the product has high solubility, bright color, excellent application performance and convenient use, and the red reactive dye for wool has strong applicability.
Description
Technical field
The present invention relates to a kind of reactive dye for wool and preparation method thereof, particularly relate to a kind of red reactive dye for wool and preparation method thereof.
Background technology
Now general dyeing wool, cashmere, used dyestuff are matching stain, acid mordant dye and metallized dye.Because with the material that these kinds of dyes are dyed, fastness is all not good enough, coloured light is not really gorgeous, but also can cause trouble to environmental protection.Get into 21 century because the restriction of environmental ecology, for dye uptake, degree of fixation and dyeing waste-water require increasingly high.Matching stain can not satisfy development of times again.
Technical problem to be solved by this invention is, provides one can reduce environmental pollution, and the desired raw material cost is low, and product solubility is high, and bright in colour, and application performance is excellent, and is easy to use, red reactive dye for wool that suitability is strong and preparation method thereof.
Summary of the invention
In order to solve the problems of the technologies described above, the invention provides a kind of red reactive dye for wool, this red reactive dye for wool is the compound with following general formula (I) structure:
The preparation method of the dye composition of said structure formula (I) comprises the steps:
The dissolving of a, H acid
Use sodium hydroxide solution to transfer the pH of H acid solution to be 6.5-7.0, the mass/volume concentration of adjustment solution is 15%, gets the H acid solution;
B, condensation reaction
Adjustment H acid solution mass/volume concentration is 10%, keeps pH=6～6.5 with sodium hydrogencarbonate, 5～10 ℃ of temperature, and 40～60 minutes times spent, add 2,3-two bromo propionyl chloros and acetone mixed solution reacted 1-3 hour, got condensated liquid.
C, diazotization reaction
A position ester between O-methoxy is dissolved in the water, and the regulator solution temperature is less than 0 ℃, and the pH that keeps solution with hydrochloric acid adds Sodium Nitrite fast less than 2, keeps 0～5 ℃ of reaction of temperature 1-3 hour, eliminates excessive nitrous acid with thionamic acid, diazonium liquid,
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, holding temperature 10-30 ℃, keep pH=5-8, reacted 3-5 hour coupling solution.
E, neutralization reaction
Coupling solution is adjusted to pH=6-6.5 with hydrochloric acid soln, stirred 10-20 minute.
F, drying
With dry formula (I) compound that gets of the solution spray of e step.
Preferably, the preparation method of the dye composition of said structure formula (I) comprises the steps:
The dissolving of a, H acid
With water dissolution H acid, transfer pH=6.5-7 with sodium hydroxide solution then, make material dissolution, clarification, the mass/volume concentration of adjustment solution is 15%, gets the H acid solution;
B, condensation reaction
Under 5～7 ℃ of temperature, adjustment H acid solution mass/volume concentration is 10%, keeps pH=6～6.5 with sodium hydrogencarbonate; 5～10 ℃ of temperature, 40～60 minutes times spent, add 2; 3-two bromo propionyl chloros and acetone mixed solution; 5～10 ℃ of holding temperatures and pH value 6～6.5 were reacted 1-3 hour, got condensated liquid.
C, diazotization reaction
Position ester between O-methoxy is dissolved in the water, adding hydrochloric acid, the regulator solution temperature is less than 0 ℃, and the pH that keeps solution adds Sodium Nitrite fast less than 2, keeps 0～5 ℃ of reaction of temperature 1-3 hour, eliminates excessive nitrous acid with thionamic acid, gets diazonium liquid,
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, and transfers pH=7 with yellow soda ash, is warmed up to 10 ℃, holding temperature 10-30 ℃, keep pH=5-8, reacted 3-5 hour coupling solution.
E, neutralization reaction
Coupling solution is adjusted to pH=6-6.5 with hydrochloric acid soln, stirred 10-20 minute.
F, drying
With dry formula (I) compound that gets of the solution spray of e step.
More preferably, the preparation method of the dye composition of said structure formula (I) comprises the steps:
The dissolving of a, H acid
In beaker, add water, add 100%H acid then, stir down and transfer pH=6.5-7, make material dissolution with 30% sodium hydroxide solution, clarification, the volume of adjustment solution, the mass/volume concentration that makes solution is 15% H acid solution.
B, condensation reaction
With direct ice and water adjustment H acid solution temperature to 5～7 ℃, adjustment liquor capacity concentration is 10%, keeps pH=6～6.5 with sodium hydrogencarbonate then; With 5～10 ℃ of direct ice holding temperatures, 40～60 minutes times spent are with 2 of suitable moles mass; 3-two bromo propionyl chloros and acetone mixed solution add; 5～10 ℃ of holding temperatures and pH value 6～6.5 were reacted 1-3 hour, got condensated liquid.
C, diazotization reaction
In beaker, add water, add position ester between O-methoxy then, stirred 10-20 minute.30% hydrochloric acid soln is added, and less than 0 ℃, adjustment mass/volume concentration is 5.5% with direct ice adjustment solution temperature; Under reaction soln guarantees that the pH value is less than 2 condition, 30% sodium nitrite solution of suitable moles mass is added 0～5 ℃ of holding temperature fast; Reacted 1-3 hour; Eliminate excessive nitrous acid with thionamic acid, get diazonium liquid
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, and transfers pH=7 with yellow soda ash, is warmed up to 10 ℃, and holding temperature 10-30 ℃, keep pH=5-8, reacted 3-5 hour.
E, neutralization reaction
Coupled reaction liquid is adjusted to pH=6-6.5 with 30% hydrochloric acid soln, stirred 10-20 minute.
F, drying
The look liquid of e step is joined in the feed liquid preheater, adjust the spray tower inlet temperature and carry out spraying drying, obtain product.
In the aforesaid method, H acid is 1-amino-8-naphthol-3, the abbreviation of 6-disulfonate sodium, and its structural formula is following:
By name the 2-methoxyl group-5-β-its structural formula of ethyl sulfuryl sulfate ester aniline is following for the chemistry of position ester between O-methoxy:
In the method for aforesaid method and hereinafter embodiment, the unit of mass/volume concentration is grams per milliliter (g/ml) or kg/liter (kg/L).
Used various raw materials all can be bought from market and obtain in the aforesaid method.
Using and preparing of the compound of the present invention's preparation can reduce environmental pollution, and the desired raw material cost is low, and product solubility is high, lovely luster, and application performance is excellent, and is easy to use, is the strong red reactive dye for wool of a kind of suitability.
Embodiment
Following embodiment just to the explanation of technical scheme of the present invention, does not form any restriction to technical scheme of the present invention and protection domain.
Embodiment 1
The dissolving of a, H acid
In 500 ml beakers, add 200 milliliters in water, add 100%H acid 34.1 grams then, stir down and transfer pH=6.5-7, make material dissolution, clarification with 30% sodium hydroxide solution.The volume of adjustment solution is 227 milliliters.The mass/volume concentration that makes solution is 15%
B, condensation reaction
With direct ice and water adjustment H acid solution temperature to 5～7 ℃, adjustment solution quality/volumetric concentration is 10%, follows 96% sodium hydrogencarbonate to keep pH=6～6.5 then; With 5～10 ℃ of direct ice holding temperatures; 50 minutes times spent, with 100% 2,3-two bromo propionyl chloros 32.6 gram and the adding of acetone mixed solution; 5～10 ℃ of holding temperatures and pH value 6～6.5, react 2 hours must condensated liquid.
C, diazotization reaction
In 800 ml beakers, add 200 milliliters in water, then 100%2-methoxyl group-5-β-ethyl sulfuryl sulfate ester aniline 31.1 grams are added, stirred 15 minutes.Again 15.8 grams, 30% hydrochloric acid soln is added.Less than 0 ℃, adjustment mass/volume concentration is 5.5% with direct ice adjustment solution temperature, under reaction soln guarantees that the pH value is less than 2 condition, with 100% Sodium Nitrite, 7.04 grams, is made into 30% sodium nitrite solution and adds fast.0～5 ℃ of holding temperature was reacted 2 hours, eliminated excessive nitrous acid with thionamic acid, got diazonium liquid
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, and transfers pH=7 with 96% yellow soda ash, is warmed up to 20 ℃, and holding temperature 20-30 ℃, keep pH=7-7.5, reacted 4 hours.
E, neutralization reaction
Coupled reaction liquid is adjusted to pH=6-6.5 with 30% hydrochloric acid soln, stirred 15 minutes.
F, drying
The look liquid of e step is joined in the feed liquid preheater, adjust the spray tower inlet temperature and carry out spraying drying.Get the orchil of formula:
The red reactive dye for wool application performance of the embodiment of the invention 1 preparation is as shown in the table:
Compound of the present invention and preparation method thereof is described through concrete embodiment.Those skilled in the art can use for reference links such as content appropriate change raw material of the present invention, processing condition and realize corresponding other purpose; Its relevant change does not all break away from content of the present invention; All similar replacements and change will become apparent to those skilled in the art that all to be regarded as and are included within the scope of the present invention.
Claims (4)
1. red reactive dye for wool, this red reactive dye for wool is the compound with following general formula (I) structure:
2. the preparation method of dyestuff according to claim 1, this method comprises the steps:
The dissolving of a, H acid
Use sodium hydroxide solution to transfer the pH of H acid solution to be 6.5-7.0, the mass/volume concentration of adjustment solution is 0.15g/ml, gets the H acid solution;
B, condensation reaction
Adjustment H acid solution mass/volume concentration is 0.10g/ml, keeps pH=6～6.5 with sodium hydrogencarbonate, 5～10 ℃ of temperature, and 40～60 minutes times spent, add 2,3-two bromo propionyl chloros and acetone mixed solution reacted 1-3 hour, got condensated liquid;
C, diazotization reaction
A position ester between O-methoxy is dissolved in the water, and the regulator solution temperature is less than 0 ℃, and the pH that keeps solution with hydrochloric acid adds Sodium Nitrite fast less than 2, keeps 0～5 ℃ of reaction of temperature 1-3 hour, eliminates excessive nitrous acid with thionamic acid, diazonium liquid,
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, holding temperature 10-30 ℃, keep pH=5-8, reacted 3-5 hour coupling solution;
E, neutralization reaction
Coupling solution is adjusted to pH=6-6.5 with hydrochloric acid soln, stirred 10-20 minute;
F, drying
With dry formula (I) compound that gets of the solution spray of e step.
3. method according to claim 2, this method comprises the steps:
The dissolving of a, H acid
With water dissolution H acid, transfer pH=6.5-7.0 with sodium hydroxide solution then, make material dissolution, clarification, the mass/volume concentration of adjustment solution is 0.15g/ml, gets the H acid solution;
B, condensation reaction
Under 5～7 ℃ of temperature, adjustment H acid solution mass and size concentration is 0.10g/ml, keeps pH=6～6.5 with sodium hydrogencarbonate; 5～10 ℃ of temperature, 40～60 minutes times spent, add 2; 3-two bromo propionyl chloros and acetone mixed solution; 5～10 ℃ of holding temperatures and pH value 6～6.5 were reacted 1-3 hour, got condensated liquid;
C, diazotization reaction
Position ester between O-methoxy is dissolved in the water, adding hydrochloric acid, the regulator solution temperature is less than 0 ℃, and the pH that keeps solution adds Sodium Nitrite fast less than 2, keeps 0～5 ℃ of reaction of temperature 1-3 hour, eliminates excessive nitrous acid with thionamic acid, gets diazonium liquid,
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, and transfers pH=7 with yellow soda ash, is warmed up to 10 ℃, holding temperature 10-30 ℃, keep pH=5-8, reacted 3-5 hour coupling solution;
E, neutralization reaction
Coupling solution is adjusted to pH=6-6.5 with hydrochloric acid soln, stirred 10-20 minute;
F, drying
With dry formula (I) compound that gets of the solution spray of e step.
4. according to claim 2 or 3 described methods, this method comprises the steps:
The dissolving of a, H acid
In beaker, add water, add 100%H acid then, stir down and transfer pH=6.5-7.0, make material dissolution with 30% sodium hydroxide solution, clarification, the volume of adjustment solution, the mass/volume concentration that makes solution is the H acid solution of 0.15g/ml;
B, condensation reaction
With direct ice and water adjustment H acid solution temperature to 5～7 ℃, adjustment solution quality/volumetric concentration is 0.10g/ml, keeps pH=6～6.5 with sodium hydrogencarbonate then; With 5～10 ℃ of direct ice holding temperatures, 40～60 minutes times spent are with 2 of suitable moles mass; 3-two bromo propionyl chloros and acetone mixed solution add; 5～10 ℃ of holding temperatures and pH value 6～6.5 were reacted 1-3 hour, got condensated liquid;
C, diazotization reaction
In beaker, add water, add position ester between O-methoxy then, stirred 10-20 minute; 30% hydrochloric acid soln is added, and less than 0 ℃, adjustment mass/volume concentration is 0.055g/ml with direct ice adjustment solution temperature; Under reaction soln guarantees that the pH value is less than 2 condition, 30% sodium nitrite solution of suitable moles mass is added 0～5 ℃ of holding temperature fast; Reacted 1-3 hour; Eliminate excessive nitrous acid with thionamic acid, get diazonium liquid
D, coupled reaction
The diazonium liquid that the c step is obtained joins in the condensated liquid that the b step obtains, and transfers pH=7 with yellow soda ash, is warmed up to 10 ℃, holding temperature 10-30 ℃, keep pH=5-8, reacted 3-5 hour coupling solution;
E, neutralization reaction
Coupled reaction liquid is adjusted to pH=6-6.5 with 30% hydrochloric acid soln, stirred 10-20 minute;
F, drying
The solution of e step is joined in the feed liquid preheater, adjust the spray tower inlet temperature and carry out spraying drying, get formula (I) compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910228596 CN101705019B (en) | 2009-11-16 | 2009-11-16 | Red reactive dye for wool and preparation method thereof |
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| CN 200910228596 CN101705019B (en) | 2009-11-16 | 2009-11-16 | Red reactive dye for wool and preparation method thereof |
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| CN101705019A CN101705019A (en) | 2010-05-12 |
| CN101705019B true CN101705019B (en) | 2012-05-02 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102433024B (en) * | 2011-09-27 | 2016-03-23 | 天津德凯化工股份有限公司 | A kind of red reactive dye for wool and preparation method thereof |
| CN102408747B (en) * | 2011-09-27 | 2016-03-23 | 天津德凯化工股份有限公司 | A kind of red reactive dyes and preparation method thereof |
| CN104277490B (en) * | 2014-09-28 | 2019-01-22 | 天津德凯化工股份有限公司 | A kind of nylon reactive dye and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0918074A1 (en) * | 1997-11-20 | 1999-05-26 | ILFORD Imaging Switzerland GmbH | Azo dyes, their preparation and use thereof |
| US6187912B1 (en) * | 2000-01-07 | 2001-02-13 | Dystar Textifarben Gmbh & Co. | Disazo compound their preparation and their use as dyestuffs |
| CN101215425A (en) * | 2008-01-22 | 2008-07-09 | 天津市德凯化工有限公司 | Red reactive dyestuffs and preparation method thereof |
-
2009
- 2009-11-16 CN CN 200910228596 patent/CN101705019B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0918074A1 (en) * | 1997-11-20 | 1999-05-26 | ILFORD Imaging Switzerland GmbH | Azo dyes, their preparation and use thereof |
| US6187912B1 (en) * | 2000-01-07 | 2001-02-13 | Dystar Textifarben Gmbh & Co. | Disazo compound their preparation and their use as dyestuffs |
| CN101215425A (en) * | 2008-01-22 | 2008-07-09 | 天津市德凯化工有限公司 | Red reactive dyestuffs and preparation method thereof |
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Address after: 300270 No. 1558 Kaixuan street, Dagang Petrochemical Industrial Park, Binhai New Area, Tianjin Patentee after: Tianjin Dek Chemical Co.,Ltd. Address before: 300163 Tianjin city Dongli District ZhangGuiZhuang road Ji'an Road Patentee before: Tianjin Dek Chemical Co.,Ltd. |
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