CN103030999A - Nylon reactive red dye and its preparation method - Google Patents
Nylon reactive red dye and its preparation method Download PDFInfo
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- CN103030999A CN103030999A CN2010102663222A CN201010266322A CN103030999A CN 103030999 A CN103030999 A CN 103030999A CN 2010102663222 A CN2010102663222 A CN 2010102663222A CN 201010266322 A CN201010266322 A CN 201010266322A CN 103030999 A CN103030999 A CN 103030999A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000004677 Nylon Substances 0.000 title claims abstract description 17
- 229920001778 nylon Polymers 0.000 title claims abstract description 17
- 239000001044 red dye Substances 0.000 title abstract description 7
- 238000005859 coupling reaction Methods 0.000 claims abstract description 23
- 239000000975 dye Substances 0.000 claims abstract description 23
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000000706 filtrate Substances 0.000 claims abstract description 15
- 238000009833 condensation Methods 0.000 claims abstract description 14
- 230000005494 condensation Effects 0.000 claims abstract description 14
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 claims abstract description 10
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims abstract description 9
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002699 waste material Substances 0.000 claims abstract description 9
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- 239000012295 chemical reaction liquid Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 235000019439 ethyl acetate Nutrition 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 12
- 238000004043 dyeing Methods 0.000 claims description 11
- 238000006193 diazotization reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 238000005507 spraying Methods 0.000 claims description 7
- 238000006482 condensation reaction Methods 0.000 claims description 6
- 239000010813 municipal solid waste Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 235000017550 sodium carbonate Nutrition 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 abstract 1
- 238000001694 spray drying Methods 0.000 abstract 1
- 238000011109 contamination Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000980 acid dye Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
The invention relates to a nylon reactive red dye and its preparation method. The dye is a compound having a structure represented by formula (I). The preparation method of the dye comprises the following steps: 1, adding an ethanolamine sulfate solution to a cyanuric chloride solution for reacting to obtain a first condensation solution, and adding a J acid to the first condensation solution to obtain a second condensation solution; 2, adding a hydrochloric acid solution and a sodium nitrite solution to 4-aminoazobenzene-4'-sulfonic acid, reacting under a condition that the pH value is less than 2, and eliminating excess nitrous acid by sulfamic acid to obtain a diazo solution; 3, adding the diazo solution obtained in step 2 to the second condensation solution obtained in step 1 in a dropwise manner to obtain a coupling reaction solution; 4, heating the coupling reaction solution obtained in step 3, maintaining the pH value in a range of 8-11, and hydrolyzing; 5, filtering the hydrolysis reaction solution obtained in step 4 to remove waste residues, and collecting the obtained filtrate; 6, carrying out colored light and intensity adjustment of the filtrate obtained in step 5; and 7, carrying out spray drying of the color solution obtained in step 6 to obtain the dye of the formula (I).
Description
Technical field
The present invention relates to a kind of nylon active dye well preparation method.Especially nylon red reactive dyes and preparation method thereof.
Background technology
Now the general nylon used dyestuff that dyes is matching stain, weak acid dye and metallized dye.Because the every wet fastness of nylon that these dyestuffs dye is not good enough, coloured light is not very gorgeous, and the low rate of clean absorption rate, the dyeing liquid waste concentration is high, and particularly heavy metal causes severe contamination to environment.Enter 21 century, because the restriction of environmental ecology, for dye uptake, the requirement of degree of fixation and dyeing waste liquid is more and more higher.Matching stain, weak acid dye and metal complex can not satisfy the dyeing nylon demand.
It is low, beautiful in colour to be badly in need of at present environmental contamination reduction and raw materials cost, the excellent nylon reactive red dye of every wet fastness properties.
Summary of the invention
In order to solve the problems of the technologies described above, the invention provides a kind of red nylon active dye well its preparation method, this dyestuff is as shown in the formula the compound shown in (I):
Wherein: M is-H or basic metal that preferred as alkali is Na or K.
The preparation method of the dye composition of above-mentioned formula (I) comprises the steps:
A, condensation reaction:
The thanomin acetic ester solution joins reaction acquisition primary condensation liquid in the cyanuric chloride solution, then adds J acid in this condensated liquid, obtains the secondary condensated liquid;
B, diazotization reaction:
In P-aminoazobenzene-4 '-sulfonic acid, add hydrochloric acid soln and sodium nitrite solution, in the situation of PH＜2, react, then eliminate excessive nitrite with thionamic acid, get diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensated liquid of a step, gets coupled reaction liquid;
D, hydrolysis reaction:
C step coupled reaction liquid is heated up, keep the pH=8-11 hydrolysis;
E, removal insolubles:
D step hydrolysis reaction liquid is filtered the removal waste residue, collect filtrate;
F, adjustment coloured light and intensity:
E step filtrate is carried out coloured light, intensity adjustment;
G, drying:
The look liquid of f step is carried out spraying drying, get formula (I) the finished product.
Preferably, the preparation method of the dye composition of above-mentioned formula (I) comprises the steps:
A, condensation reaction:
The thanomin acetic ester solution of pH=2-5 is joined in the cyanuric chloride solution, keep T=0-15 ℃, pH=2-3.5 reacted 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, add J acid, adjust T=15-40 ℃, pH=4-6 reacted 2-4 hour, obtained the secondary condensated liquid;
B, diazotization reaction:
Add hydrochloric acid soln and sodium nitrite solution in low temperature P-aminoazobenzene-4 '-sulfonic acid, at T=0-20 ℃, reacted 1-3 hour PH＜2, eliminates excessive nitrite with thionamic acid, gets diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensated liquid of a step, keeps T=10-20 ℃, pH=5-7 reacted 1-2 hour, got coupled reaction liquid;
D, hydrolysis reaction:
C step coupled reaction liquid is warming up to 30-50 ℃, keeps pH=8-11, reacted 5-7 hour;
E, removal insolubles:
D step hydrolysis reaction liquid is joined in the solid-liquid separator, separate, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of e step filtrate, carry out coloured light, intensity adjustment according to coloration result again;
G, drying:
The look liquid of f step is joined in the feed liquid preheater, adjust inlet temperature and temperature out and carry out spraying drying, get formula (I) the finished product.
Preferably, the preparation method of the dye composition of above-mentioned formula (I) comprises the steps:
A, condensation reaction:
In dissolving vessel, add water of a small amount of end and thanomin acetic ester, use NaHCO
3Be neutralized to pH=2-5, get the thanomin acetic ester solution; In reactor, add a small amount of water and a small amount of trash ice, add again cyanuric chloride, in the stirring, drip the thanomin acetic ester solution, T=0-15 ℃, pH=2-3.5 dropwises, and reacts 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, add J acid, adjust T=15-40 ℃, pH=4-6, reacted 2-4 hour, and obtained the secondary condensated liquid;
B, diazotization reaction:
Add end water and P-aminoazobenzene-4 '-sulfonic acid in reactor, stir, add hydrochloric acid soln and the sodium nitrite solution of trash ice and 30%, at T=0-20 ℃, reacted 1-3 hour PH＜2, eliminates excessive nitrite with thionamic acid, gets diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensated liquid of a step, in the dropping process T=10-20 ℃, transfer pH=5-7 with soda ash, drip and finish, reacted 1-2 hour, get coupled reaction liquid;
D, hydrolysis reaction:
C step coupled reaction liquid is warming up to 30-50 ℃, keeps pH=8-11 with soda ash, reacted 5-7 hour;
E, removal insolubles:
D step hydrolysis reaction liquid is joined in the solid-liquid separator, separate, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of e step filtrate, carry out coloured light, intensity adjustment according to coloration result again;
G, drying:
The look liquid of f step is joined in the feed liquid preheater, adjust 210 ℃ of inlet temperatures, carry out spraying drying with 95-100 ℃ temperature out, get formula (I) the finished product.
In the aforesaid method, preferably, in the primary condensation liquid preparation T=5-10 ℃, the reaction times is 5 hours;
In the aforesaid method, preferably, in the secondary condensated liquid preparation T=20-30 ℃, the reaction times is 3 hours;
In the aforesaid method, preferably, in the diazotization reaction T=5-15 ℃, the reaction times is 2 hours;
Wherein the structure of thanomin acetic ester is as follows:
H
2NCH
2CH
2OCOCH
3
The structure of cyanuric chloride is as follows:
The structure of J acid is as follows:
The structure of P-aminoazobenzene-4 '-sulfonic acid is as follows:
Used intermediate all is disclosed known compound in the prior art in the aforesaid method, all can buy from the market to obtain.
In the aforesaid method, what T represented is temperature, and for example T=10-20 ℃, the expression temperature is between 10-20 ℃.
The present invention also provides a kind of composition for dyeing nylon, and said composition comprises dye composition and the dyestuff carrier of formula (I).
The present invention also provides the dye composition of above-mentioned formula (I) to be used for the purposes of dyeing nylon.
The preparation of the dyestuff of above-mentioned formula (I) compound and use can environmental contamination reduction particularly reduces the pollution of heavy metal.And the desired raw material cost is low, and is beautiful in colour, every wet fastness, such as wet rub, soap, the excellent performances such as alkali sweat, sour sweat, washing, easy to use, be the excellent nylon reactive red dye that is applicable to dyeing nylon.
Embodiment
The preparation of the nylon reactive red dye compound of embodiment 1 structural formula (II)
The preparation of a, condenses:
In dissolving vessel, add water of a small amount of end and thanomin acetic ester 27Kg, use NaHCO
3In and pH=4-5, get the thanomin acetic ester solution; In reactor, add a small amount of water and a small amount of trash ice, add again cyanuric chloride 19Kg, in the stirring, drip the thanomin acetic ester, T=0-15 ℃, pH=2-3.5 dropwises, and reacts 5 hours, gets primary condensation liquid; Add J acid 26.5Kg in primary condensation liquid, adjust T=35-40 ℃, pH=5-6 reacted 3 hours, got the secondary condensated liquid.
B, P-aminoazobenzene-4 '-sulfonic acid diazotization:
In reactor, add end water, P-aminoazobenzene-4 '-sulfonic acid 23.2Kg, stir, add trash ice, 30% hydrochloric acid soln and sodium nitrite solution.At 15-20 ℃, reacted 2 hours PH＜2, and (starch potassium iodide paper is little blueness after soaking), eliminate excessive nitrite with thionamic acid, get diazo liquid.
C, coupled reaction:
The diazo liquid that the b step is obtained is added drop-wise in a step secondary condensated liquid, drips T=15-20 ℃ of process, transfers pH=5-7 with soda ash, drips and finishes, and reacts 2 hours, gets coupled reaction liquid.
D, hydrolysis reaction:
C step coupled reaction liquid is warming up to 45-50 ℃, keeps pH=10-11 with soda ash, reacted 6 hours.
E, removal insolubles:
D step hydrolysis reaction liquid is joined in the solid-liquid separator, separate, remove waste residue, collect filtrate in storage tank.
F, adjustment coloured light and intensity:
With the dyeing of e step material, carry out coloured light, intensity adjustment according to coloration result again
G, drying:
The look liquid of f step is joined in the feed liquid preheater, adjust 210 ℃ of inlet temperatures, carry out spraying drying with 95-100 ℃ temperature out, get the finished product 104Kg.
The application performance table of the nylon reactive red dye of the formula of embodiment 1 (II)
The preparation method of dyestuff of the present invention and dyestuff thereof is described by specific embodiment.Those skilled in the art can use for reference the 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 and all be deemed to be included within the scope of the present invention.
Claims (7)
1. red nylon active dyestuff, this dyestuff is as shown in the formula the compound shown in (I):
Wherein: M is-H or basic metal that preferred as alkali is Na or K.
2. the preparation method of dyestuff claimed in claim 1, the method comprises the steps:
A, condensation reaction:
The thanomin acetic ester solution joins reaction acquisition primary condensation liquid in the cyanuric chloride solution, then adds J acid in this condensated liquid, obtains the secondary condensated liquid;
B, diazotization reaction:
In P-aminoazobenzene-4 '-sulfonic acid, add hydrochloric acid soln and sodium nitrite solution, in the situation of PH＜2, react, then eliminate excessive nitrite with thionamic acid, get diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensated liquid of a step, gets coupled reaction liquid;
D, hydrolysis reaction:
C step coupled reaction liquid is heated up, keep the pH=8-11 hydrolysis;
E, removal insolubles:
D step hydrolysis reaction liquid is filtered the removal waste residue, collect filtrate;
F, adjustment coloured light and intensity:
E step filtrate is carried out coloured light, intensity adjustment;
G, drying:
The look liquid of f step is carried out spraying drying, get formula (I) the finished product.
3. method according to claim 2, the method comprises the steps:
A, condensation reaction:
The thanomin acetic ester solution of pH=2-5 is joined in the cyanuric chloride solution, keep T=0-15 ℃, pH=2-3.5 reacted 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, add J acid, adjust T=15-40 ℃, pH=4-6 reacted 2-4 hour, obtained the secondary condensated liquid;
B, diazotization reaction:
Add hydrochloric acid soln and sodium nitrite solution in low temperature P-aminoazobenzene-4 '-sulfonic acid, at T=0-20 ℃, reacted 1-3 hour PH＜2, eliminates excessive nitrite with thionamic acid, gets diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensated liquid of a step, keeps T=10-20 ℃, pH=5-7 reacted 1-2 hour, got coupled reaction liquid;
D, hydrolysis reaction:
C step coupled reaction liquid is warming up to 30-50 ℃, keeps pH=8-11, reacted 5-7 hour;
E, removal insolubles:
D step hydrolysis reaction liquid is joined in the solid-liquid separator, separate, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of e step filtrate, carry out coloured light, intensity adjustment according to coloration result again;
G, drying:
The look liquid of f step is joined in the feed liquid preheater, adjust inlet temperature and temperature out and carry out spraying drying, get formula (I) the finished product.
4. described method according to claim 2-3, the method comprises the steps:
A, condensation reaction:
In dissolving vessel, add water of a small amount of end and thanomin acetic ester, use NaHCO
3Be neutralized to pH=2-5, get the thanomin acetic ester solution; In reactor, add a small amount of water and a small amount of trash ice, add again cyanuric chloride, in the stirring, drip the thanomin acetic ester solution, T=0-15 ℃, pH=2-3.5 dropwises, and reacts 4-6 hour, obtain primary condensation liquid, then in this condensated liquid, add J acid, adjust T=15-40 ℃, pH=4-6, reacted 2-4 hour, and obtained the secondary condensated liquid;
B, diazotization reaction:
Add end water and P-aminoazobenzene-4 '-sulfonic acid in reactor, stir, add hydrochloric acid soln and the sodium nitrite solution of trash ice and 30%, at T=0-20 ℃, reacted 1-3 hour PH＜2, eliminates excessive nitrite with thionamic acid, gets diazo liquid;
C, coupled reaction:
B step gained diazo liquid is added drop-wise in the secondary condensated liquid of a step, in the dropping process T=10-20 ℃, transfer pH=5-7 with soda ash, drip and finish, reacted 1-2 hour, get coupled reaction liquid;
D, hydrolysis reaction:
C step coupled reaction liquid is warming up to 30-50 ℃, keeps pH=8-11 with soda ash, reacted 5-7 hour;
E, removal insolubles:
D step hydrolysis reaction liquid is joined in the solid-liquid separator, separate, remove waste residue, collect filtrate in storage tank;
F, adjustment coloured light and intensity:
With the dyeing of e step filtrate, carry out coloured light, intensity adjustment according to coloration result again;
G, drying:
The look liquid of f step is joined in the feed liquid preheater, adjust 210 ℃ of inlet temperatures, carry out spraying drying with 95-100 ℃ temperature out, get formula (I) the finished product.
5. method according to claim 4, wherein in the preparation of primary condensation liquid T=5-10 ℃, the reaction times is 5 hours.
6. method according to claim 4, wherein in the preparation of secondary condensated liquid T=20-30 ℃, the reaction times is 3 hours.
7. method according to claim 4, wherein in the diazotization reaction T=5-15 ℃, the reaction times is 2 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102663222A CN103030999A (en) | 2010-08-30 | 2010-08-30 | Nylon reactive red dye and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102663222A CN103030999A (en) | 2010-08-30 | 2010-08-30 | Nylon reactive red dye and its preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103030999A true CN103030999A (en) | 2013-04-10 |
Family
ID=48018421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102663222A Pending CN103030999A (en) | 2010-08-30 | 2010-08-30 | Nylon reactive red dye and its preparation method |
Country Status (1)
| Country | Link |
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| CN (1) | CN103030999A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107385995A (en) * | 2017-06-12 | 2017-11-24 | 安徽中亚纸业有限公司 | A kind of paper environment-friendly dye composition |
| CN112210228A (en) * | 2020-10-23 | 2021-01-12 | 浙江亿得新材料股份有限公司 | Preparation process of high-fastness and high-solubility red dye |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5886159A (en) * | 1996-08-23 | 1999-03-23 | Sumitomo Chemical Company, Limited | Bisazo compound and method for dyeing or printing fibrous materials using the same |
| US5969113A (en) * | 1995-09-21 | 1999-10-19 | Ciba Specialty Chemicals Corporation | Reactive dyes, their preparation and use |
| US5998591A (en) * | 1997-05-22 | 1999-12-07 | Sumitomo Chemical Company, Limited | Fiber-reactive bisazo compound |
| JP2001348506A (en) * | 2000-06-09 | 2001-12-18 | Sumitomo Chem Co Ltd | Reactive dye composition and its application to fiber materials |
| US6372893B1 (en) * | 1999-11-01 | 2002-04-16 | Clariant Finance (Bvi) Limited | AZO dyestuffs |
| CN101307186A (en) * | 2008-06-20 | 2008-11-19 | 上虞新晟化工工业有限公司 | A kind of red disazo dye compound, preparation method and composition thereof |
-
2010
- 2010-08-30 CN CN2010102663222A patent/CN103030999A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5969113A (en) * | 1995-09-21 | 1999-10-19 | Ciba Specialty Chemicals Corporation | Reactive dyes, their preparation and use |
| US5886159A (en) * | 1996-08-23 | 1999-03-23 | Sumitomo Chemical Company, Limited | Bisazo compound and method for dyeing or printing fibrous materials using the same |
| US5998591A (en) * | 1997-05-22 | 1999-12-07 | Sumitomo Chemical Company, Limited | Fiber-reactive bisazo compound |
| US6372893B1 (en) * | 1999-11-01 | 2002-04-16 | Clariant Finance (Bvi) Limited | AZO dyestuffs |
| JP2001348506A (en) * | 2000-06-09 | 2001-12-18 | Sumitomo Chem Co Ltd | Reactive dye composition and its application to fiber materials |
| CN101307186A (en) * | 2008-06-20 | 2008-11-19 | 上虞新晟化工工业有限公司 | A kind of red disazo dye compound, preparation method and composition thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107385995A (en) * | 2017-06-12 | 2017-11-24 | 安徽中亚纸业有限公司 | A kind of paper environment-friendly dye composition |
| CN112210228A (en) * | 2020-10-23 | 2021-01-12 | 浙江亿得新材料股份有限公司 | Preparation process of high-fastness and high-solubility red dye |
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Application publication date: 20130410 |