CN102146061B - 一种红色活性染料化合物、其制备方法及含其的染料 - Google Patents
一种红色活性染料化合物、其制备方法及含其的染料 Download PDFInfo
- Publication number
- CN102146061B CN102146061B CN 201010108235 CN201010108235A CN102146061B CN 102146061 B CN102146061 B CN 102146061B CN 201010108235 CN201010108235 CN 201010108235 CN 201010108235 A CN201010108235 A CN 201010108235A CN 102146061 B CN102146061 B CN 102146061B
- Authority
- CN
- China
- Prior art keywords
- compound
- reaction
- reactive dye
- red reactive
- carrying
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- 239000000985 reactive dye Substances 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000000975 dye Substances 0.000 title abstract description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 25
- 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
- 229940126062 Compound A Drugs 0.000 claims description 12
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 12
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 230000035484 reaction time Effects 0.000 claims description 10
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 2
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 238000004065 wastewater treatment Methods 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 description 20
- 238000006482 condensation reaction Methods 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KVWWLQUBOOFCCS-UHFFFAOYSA-N 1-ethylsulfonylethane;sulfuric acid Chemical compound OS(O)(=O)=O.CCS(=O)(=O)CC KVWWLQUBOOFCCS-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 229910004727 OSO3H Inorganic materials 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005185 salting out Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 4
- 125000006414 CCl Chemical group ClC* 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004537 pulping Methods 0.000 description 4
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910006069 SO3H Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 0 CCOc(c(c(cc1*)cc(*)c2)c2NC(N=C(C)I)=C)c1N=NC Chemical compound CCOc(c(c(cc1*)cc(*)c2)c2NC(N=C(C)I)=C)c1N=NC 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000979 synthetic dye Substances 0.000 description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical compound ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- DAEUOTLSJGVBBZ-UTTVJGTNSA-N C/C=C(\C=C(/C)\N)/S(O)(=O)=O Chemical compound C/C=C(\C=C(/C)\N)/S(O)(=O)=O DAEUOTLSJGVBBZ-UTTVJGTNSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- JGIGXKSJLSQJGQ-UHFFFAOYSA-K trisodium 5-[[4-chloro-6-(N-methylanilino)-1,3,5-triazin-2-yl]amino]-4-hydroxy-3-[(2-sulfonatophenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].CN(c1ccccc1)c1nc(Cl)nc(Nc2cc(cc3cc(c(N=Nc4ccccc4S([O-])(=O)=O)c(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)n1 JGIGXKSJLSQJGQ-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010108235 CN102146061B (zh) | 2010-02-09 | 2010-02-09 | 一种红色活性染料化合物、其制备方法及含其的染料 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010108235 CN102146061B (zh) | 2010-02-09 | 2010-02-09 | 一种红色活性染料化合物、其制备方法及含其的染料 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102146061A CN102146061A (zh) | 2011-08-10 |
CN102146061B true CN102146061B (zh) | 2013-04-03 |
Family
ID=44420553
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201010108235 Active CN102146061B (zh) | 2010-02-09 | 2010-02-09 | 一种红色活性染料化合物、其制备方法及含其的染料 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102146061B (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102584786A (zh) * | 2011-12-28 | 2012-07-18 | 泰兴锦云染料有限公司 | 活性艳红la及其制备工艺 |
CN104194395B (zh) * | 2014-08-06 | 2017-04-12 | 浙江瑞华化工有限公司 | 活性红染料组合物、活性红染料及其制备方法和应用 |
CN105038312B (zh) * | 2015-05-29 | 2017-10-20 | 浙江龙盛集团股份有限公司 | 一种红色活性染料化合物及其制备和应用 |
CN111925666A (zh) * | 2020-08-20 | 2020-11-13 | 浙江亿得新材料股份有限公司 | 一种高日晒红色活性染料及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1351636A (zh) * | 1999-05-19 | 2002-05-29 | 宝洁公司 | 活性染料化合物 |
CN1861696A (zh) * | 2006-06-19 | 2006-11-15 | 湖北华丽染料工业有限公司 | 一种偶氮染料混合物 |
CN101037546A (zh) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | 一种复合活性黑染料 |
CN101068888A (zh) * | 2004-11-12 | 2007-11-07 | 亨斯迈先进材料(瑞士)有限公司 | 活性染料、它们的制备方法及其用途 |
-
2010
- 2010-02-09 CN CN 201010108235 patent/CN102146061B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1351636A (zh) * | 1999-05-19 | 2002-05-29 | 宝洁公司 | 活性染料化合物 |
CN101068888A (zh) * | 2004-11-12 | 2007-11-07 | 亨斯迈先进材料(瑞士)有限公司 | 活性染料、它们的制备方法及其用途 |
CN1861696A (zh) * | 2006-06-19 | 2006-11-15 | 湖北华丽染料工业有限公司 | 一种偶氮染料混合物 |
CN101037546A (zh) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | 一种复合活性黑染料 |
Also Published As
Publication number | Publication date |
---|---|
CN102146061A (zh) | 2011-08-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102108214B (zh) | 一种活性黄染料化合物、其制备方法及含其的活性黄染料 | |
CN102146061B (zh) | 一种红色活性染料化合物、其制备方法及含其的染料 | |
CN104277493B (zh) | 兼有高水洗牢度和耐摩擦牢度反应性红色染料及制备方法 | |
CN102329521B (zh) | 一种红色活性染料及其制备方法 | |
CN102433026A (zh) | 纯棉或棉毛混纺织品染色用黑色活性染料及其制备方法 | |
CN104592786B (zh) | 一种新型特深反应性橙色或黄色染料及其制备方法 | |
CN104341795B (zh) | 一种高水洗牢度的反应性黄色染料及其制备方法 | |
CN107892823B (zh) | 一类具有偶氮苯并噻唑结构的适合于超临界二氧化碳无水羊毛染色的分散染料及其制备方法 | |
CN105860580B (zh) | 一种橙色活性染料的制备方法 | |
CN110066527B (zh) | 一种红色活性染料及其制备方法 | |
CN109796786B (zh) | 一种复合型鲜艳红色活性染料及其制备方法与应用 | |
CN102504594B (zh) | 一种活性红染料组合物 | |
CN110878176B (zh) | 一种活性染料化合物及其制备方法 | |
CN103030990A (zh) | 一种偶氮化合物的应用 | |
CN107141265A (zh) | 一种偶氮类化合物、其制备方法、中间体及应用 | |
CN107141264A (zh) | 一种偶氮类化合物、其制备方法、中间体及应用 | |
CN104710835B (zh) | 一种红色活性染料及其应用 | |
CN104277490A (zh) | 一种尼龙活性染料及其制备方法 | |
CN116178984B (zh) | 一种嫩黄色活性染料及其制备方法 | |
CN101914300B (zh) | 一种x型活性耐光橙色偶氮染料及其制备方法 | |
CN106883639A (zh) | 一种高固色率异双活性基的偶氮蒽醌混合发色体系的红光黑活性染料及其制备方法和应用 | |
CN116218254B (zh) | 一种艳红色活性染料及其制备方法 | |
CN110041729B (zh) | 一种橙红色活性染料及其制备方法 | |
CN102911528A (zh) | 一种耐晒、耐氯浸复合活性艳红染料 | |
CN106675089A (zh) | 一种活性橙染料的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee |
Owner name: SHANGHAI ANOKY GROUP CO., LTD. Free format text: FORMER NAME: SHANGHAI ANOKY TEXTILE CHEMICALS CO., LTD. |
|
CP01 | Change in the name or title of a patent holder |
Address after: Liantang Town Qingpu District Shanghai city 201717 Zhu Feng Road No. 6188 room 2622 Patentee after: SHANGHAI ANOKY GROUP Co.,Ltd. Address before: Liantang Town Qingpu District Shanghai city 201717 Zhu Feng Road No. 6188 room 2622 Patentee before: SHANGHAI ANOKY TEXTILE CHEMICALS Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20171116 Address after: 224631 Jiangsu province Yancheng City county road six North Ring Chen Zhen Wei Patentee after: JIANGSU ANOKY CHEMICALS Co.,Ltd. Address before: Liantang Town Qingpu District Shanghai city 201717 Zhu Feng Road No. 6188 room 2622 Patentee before: SHANGHAI ANOKY GROUP Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190806 Address after: 201703 Shanghai city Qingpu District Songhua Road No. 881 Co-patentee after: YANTAI ANOKY FINE CHEMICALS Co.,Ltd. Patentee after: SHANGHAI ANOKY GROUP Co.,Ltd. Co-patentee after: SHANGHAI ANOKY DIGITAL TECHNOLOGY Co.,Ltd. Co-patentee after: DONGYING ANOKY TEXTILE MATERIALS Co.,Ltd. Co-patentee after: SHANGHAI SHANGHU DIGITAL TECHNOLOGY Co.,Ltd. Co-patentee after: Yantai Shangyu Digital Technology Co.,Ltd. Address before: 224631 North of Weiliu Road, Chenjiagang Town, Xiangshui County, Yancheng City, Jiangsu Province Patentee before: JIANGSU ANOKY CHEMICALS Co.,Ltd. |
|
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: No. 881, Songhua Road, Qingpu District, Shanghai City, Shanghai Patentee after: SHANGHAI ANOKY GROUP Co.,Ltd. Country or region after: China Patentee after: YANTAI ANOKY FINE CHEMICALS Co.,Ltd. Patentee after: Shanghai Annuoqi Material Technology Co.,Ltd. Patentee after: DONGYING ANOKY TEXTILE MATERIALS Co.,Ltd. Patentee after: SHANGHAI SHANGHU DIGITAL TECHNOLOGY Co.,Ltd. Patentee after: Yantai Shangyu Digital Technology Co.,Ltd. Address before: No. 881, Songhua Road, Qingpu District, Shanghai City, Shanghai Patentee before: SHANGHAI ANOKY GROUP Co.,Ltd. Country or region before: China Patentee before: YANTAI ANOKY FINE CHEMICALS Co.,Ltd. Patentee before: SHANGHAI ANOKY DIGITAL TECHNOLOGY Co.,Ltd. Patentee before: DONGYING ANOKY TEXTILE MATERIALS Co.,Ltd. Patentee before: SHANGHAI SHANGHU DIGITAL TECHNOLOGY Co.,Ltd. Patentee before: Yantai Shangyu Digital Technology Co.,Ltd. |