CN102146061B - Red reactive dye compound, preparation method of red reactive dye compound and dye containing red reactive dye compound - Google Patents
Red reactive dye compound, preparation method of red reactive dye compound and dye containing red reactive dye compound Download PDFInfo
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- 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
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 239000000985 reactive dye Substances 0.000 title claims abstract description 21
- 239000000975 dye Substances 0.000 title abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 28
- 239000012467 final product Substances 0.000 claims description 18
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 16
- 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 14
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 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
- 239000002253 acid Substances 0.000 claims description 9
- 238000001514 detection method Methods 0.000 claims description 8
- 229960000890 hydrocortisone Drugs 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims description 2
- 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 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims 3
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 238000004065 wastewater treatment Methods 0.000 abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006482 condensation reaction Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010298 pulverizing process Methods 0.000 description 6
- 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
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000010009 beating Methods 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- -1 ethyl sulfonyl sulfate Chemical compound 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- 229920000742 Cotton Polymers 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
- 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 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
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 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
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical group [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XWZDJOJCYUSIEY-UHFFFAOYSA-L disodium 5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(N=Nc2ccccc2)c(cc2cc(cc(Nc3nc(Cl)nc(Cl)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O XWZDJOJCYUSIEY-UHFFFAOYSA-L 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000005183 environmental health Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 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
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Abstract
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CN 201010108235 CN102146061B (en) | 2010-02-09 | 2010-02-09 | Red reactive dye compound, preparation method of red reactive dye compound and dye containing red reactive dye compound |
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CN 201010108235 CN102146061B (en) | 2010-02-09 | 2010-02-09 | Red reactive dye compound, preparation method of red reactive dye compound and dye containing red reactive dye compound |
Publications (2)
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CN102146061A CN102146061A (en) | 2011-08-10 |
CN102146061B true CN102146061B (en) | 2013-04-03 |
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CN 201010108235 Active CN102146061B (en) | 2010-02-09 | 2010-02-09 | Red reactive dye compound, preparation method of red reactive dye compound and dye containing red reactive dye compound |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102584786A (en) * | 2011-12-28 | 2012-07-18 | 泰兴锦云染料有限公司 | Activity-brilliant-red LA and preparation method thereof |
CN104194395B (en) * | 2014-08-06 | 2017-04-12 | 浙江瑞华化工有限公司 | Reactive red dye composition, reactive red dye as well as preparation method and application of active red dye |
CN105038312B (en) * | 2015-05-29 | 2017-10-20 | 浙江龙盛集团股份有限公司 | A kind of red reactive dyes compound and its preparation and application |
CN111925666A (en) * | 2020-08-20 | 2020-11-13 | 浙江亿得新材料股份有限公司 | High-solarization red reactive dye and preparation method thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1351636A (en) * | 1999-05-19 | 2002-05-29 | 宝洁公司 | Reactive dye compounds |
CN1861696A (en) * | 2006-06-19 | 2006-11-15 | 湖北华丽染料工业有限公司 | Ozo dye mixture |
CN101037546A (en) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | Compound active black dye |
CN101068888A (en) * | 2004-11-12 | 2007-11-07 | 亨斯迈先进材料(瑞士)有限公司 | Reactive dyes, a process for their preparation and their use |
-
2010
- 2010-02-09 CN CN 201010108235 patent/CN102146061B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1351636A (en) * | 1999-05-19 | 2002-05-29 | 宝洁公司 | Reactive dye compounds |
CN101068888A (en) * | 2004-11-12 | 2007-11-07 | 亨斯迈先进材料(瑞士)有限公司 | Reactive dyes, a process for their preparation and their use |
CN1861696A (en) * | 2006-06-19 | 2006-11-15 | 湖北华丽染料工业有限公司 | Ozo dye mixture |
CN101037546A (en) * | 2007-05-10 | 2007-09-19 | 湖北华丽染料工业有限公司 | Compound active black dye |
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CN102146061A (en) | 2011-08-10 |
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Owner name: SHANGHAI ANOKY GROUP CO., LTD. Free format text: FORMER NAME: SHANGHAI ANOKY TEXTILE CHEMICALS CO., LTD. |
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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. |
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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. |
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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. |
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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. |