DE3202120A1 - "wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu deren herstellung und ihre verwendng als farbstoffe" - Google Patents
"wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu deren herstellung und ihre verwendng als farbstoffe"Info
- Publication number
- DE3202120A1 DE3202120A1 DE19823202120 DE3202120A DE3202120A1 DE 3202120 A1 DE3202120 A1 DE 3202120A1 DE 19823202120 DE19823202120 DE 19823202120 DE 3202120 A DE3202120 A DE 3202120A DE 3202120 A1 DE3202120 A1 DE 3202120A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- general formula
- carbon atoms
- compound
- substituted
- 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.)
- Withdrawn
Links
- -1 COPPER COMPLEX DISAZO COMPOUNDS Chemical class 0.000 title claims description 112
- 238000000034 method Methods 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 238000004043 dyeing Methods 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000010949 copper Substances 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000000020 sulfo group Chemical class O=S(=O)([*])O[H] 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 150000001989 diazonium salts Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000000243 solution Substances 0.000 description 25
- 229920003043 Cellulose fiber Polymers 0.000 description 14
- 239000002657 fibrous material Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 13
- 239000000985 reactive dye Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 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 description 11
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000003792 electrolyte Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 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 description 5
- 239000004952 Polyamide Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- HCVJOAPKKBMCJV-UHFFFAOYSA-N NC1C(O)=CC=CC1=S(=O)=O Chemical compound NC1C(O)=CC=CC1=S(=O)=O HCVJOAPKKBMCJV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010409 ironing Methods 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GONYTQWUTDVINV-UHFFFAOYSA-N 2-amino-5-ethenylsulfonylphenol Chemical compound NC1=CC=C(S(=O)(=O)C=C)C=C1O GONYTQWUTDVINV-UHFFFAOYSA-N 0.000 description 2
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 2
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 239000012928 buffer substance Substances 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- HMSBXLTWCMFPDZ-UHFFFAOYSA-N 2,4-dichloro-6-ethoxy-1,3,5-triazine Chemical compound CCOC1=NC(Cl)=NC(Cl)=N1 HMSBXLTWCMFPDZ-UHFFFAOYSA-N 0.000 description 1
- JKAPWXKZLYJQJJ-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-1,3,5-triazine Chemical compound COC1=NC(Cl)=NC(Cl)=N1 JKAPWXKZLYJQJJ-UHFFFAOYSA-N 0.000 description 1
- MWPZLWRHHPWTFS-UHFFFAOYSA-N 2,4-dichloro-6-methylsulfanyl-1,3,5-triazine Chemical compound CSC1=NC(Cl)=NC(Cl)=N1 MWPZLWRHHPWTFS-UHFFFAOYSA-N 0.000 description 1
- ACMVCGAZNQJQFJ-UHFFFAOYSA-N 2,4-dichloro-6-phenoxy-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(OC=2C=CC=CC=2)=N1 ACMVCGAZNQJQFJ-UHFFFAOYSA-N 0.000 description 1
- AHKWZLWMIZHTLU-UHFFFAOYSA-N 2,4-dichloro-6-phenylsulfanyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(SC=2C=CC=CC=2)=N1 AHKWZLWMIZHTLU-UHFFFAOYSA-N 0.000 description 1
- MUEJUOUFUTUSED-UHFFFAOYSA-N 2,4-dichloro-6-piperidin-1-yl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(N2CCCCC2)=N1 MUEJUOUFUTUSED-UHFFFAOYSA-N 0.000 description 1
- SVHHRUHQFRFOIQ-UHFFFAOYSA-N 2,4-dichloro-6-propoxy-1,3,5-triazine Chemical compound CCCOC1=NC(Cl)=NC(Cl)=N1 SVHHRUHQFRFOIQ-UHFFFAOYSA-N 0.000 description 1
- RWNMGRDIEPZMDG-UHFFFAOYSA-N 2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-5-methylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 RWNMGRDIEPZMDG-UHFFFAOYSA-N 0.000 description 1
- PKDSCMNHMYCMIH-UHFFFAOYSA-N 2-amino-4-ethenylsulfonylphenol Chemical compound NC1=CC(S(=O)(=O)C=C)=CC=C1O PKDSCMNHMYCMIH-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- OBXUKZGSGNXPSH-UHFFFAOYSA-N 2-phenoxy-1,3,5-triazine Chemical compound N=1C=NC=NC=1OC1=CC=CC=C1 OBXUKZGSGNXPSH-UHFFFAOYSA-N 0.000 description 1
- SFTJUQRNFXITDQ-UHFFFAOYSA-N 3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(NC=2N=C(Cl)N=C(Cl)N=2)=C1 SFTJUQRNFXITDQ-UHFFFAOYSA-N 0.000 description 1
- VNWVMZDJPMCAKD-UHFFFAOYSA-N 3-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1O VNWVMZDJPMCAKD-UHFFFAOYSA-N 0.000 description 1
- MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 1
- HYWCPNMPNFJCMD-UHFFFAOYSA-N 4,6-dichloro-n,n-diethyl-1,3,5-triazin-2-amine Chemical compound CCN(CC)C1=NC(Cl)=NC(Cl)=N1 HYWCPNMPNFJCMD-UHFFFAOYSA-N 0.000 description 1
- KXQVQPSJOYRHJB-UHFFFAOYSA-N 4,6-dichloro-n-(2,3-dimethylphenyl)-1,3,5-triazin-2-amine Chemical compound CC1=CC=CC(NC=2N=C(Cl)N=C(Cl)N=2)=C1C KXQVQPSJOYRHJB-UHFFFAOYSA-N 0.000 description 1
- NXESWKOOFSNXRQ-UHFFFAOYSA-N 4,6-dichloro-n-(4-chlorophenyl)-1,3,5-triazin-2-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 NXESWKOOFSNXRQ-UHFFFAOYSA-N 0.000 description 1
- BUCOSULJIXFZHS-UHFFFAOYSA-N 4,6-dichloro-n-(4-ethoxyphenyl)-1,3,5-triazin-2-amine Chemical compound C1=CC(OCC)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 BUCOSULJIXFZHS-UHFFFAOYSA-N 0.000 description 1
- TYGVZWLFENCCCW-UHFFFAOYSA-N 4,6-dichloro-n-(4-methylphenyl)-1,3,5-triazin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 TYGVZWLFENCCCW-UHFFFAOYSA-N 0.000 description 1
- NPYDPROENPLGBR-UHFFFAOYSA-N 4,6-dichloro-n-cyclohexyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC2CCCCC2)=N1 NPYDPROENPLGBR-UHFFFAOYSA-N 0.000 description 1
- QRTBWWIIFMMESL-UHFFFAOYSA-N 4,6-dichloro-n-methyl-1,3,5-triazin-2-amine Chemical compound CNC1=NC(Cl)=NC(Cl)=N1 QRTBWWIIFMMESL-UHFFFAOYSA-N 0.000 description 1
- OXGUSMYPAKGXRF-UHFFFAOYSA-N 4,6-dichloro-n-methyl-n-phenyl-1,3,5-triazin-2-amine Chemical compound N=1C(Cl)=NC(Cl)=NC=1N(C)C1=CC=CC=C1 OXGUSMYPAKGXRF-UHFFFAOYSA-N 0.000 description 1
- JDAPQMINSZDTBM-UHFFFAOYSA-N 4,6-dichloro-n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC(Cl)=NC(Cl)=N1 JDAPQMINSZDTBM-UHFFFAOYSA-N 0.000 description 1
- JXMNIFBDZUCJHU-UHFFFAOYSA-N 4,6-dichloro-n-propyl-1,3,5-triazin-2-amine Chemical compound CCCNC1=NC(Cl)=NC(Cl)=N1 JXMNIFBDZUCJHU-UHFFFAOYSA-N 0.000 description 1
- UQAMDAUJTXFNAD-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1 UQAMDAUJTXFNAD-UHFFFAOYSA-N 0.000 description 1
- JDBGDMZILOWAHV-UHFFFAOYSA-N 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 JDBGDMZILOWAHV-UHFFFAOYSA-N 0.000 description 1
- MTBNVBBMBVPJHP-UHFFFAOYSA-N 4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 MTBNVBBMBVPJHP-UHFFFAOYSA-N 0.000 description 1
- ZFRBZRZEKIOGQI-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=CC(O)=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 ZFRBZRZEKIOGQI-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VEJVTSWYPIZEPD-UHFFFAOYSA-N 4-phenoxy-1,3,5-triazine-2-sulfonic acid Chemical compound S(=O)(=O)(O)C1=NC(=NC=N1)OC1=CC=CC=C1 VEJVTSWYPIZEPD-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- GHRFKYLRLYCCCV-UHFFFAOYSA-N BrN1NC=CC(=N1)Br Chemical class BrN1NC=CC(=N1)Br GHRFKYLRLYCCCV-UHFFFAOYSA-N 0.000 description 1
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 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 description 1
- CIYATNIICRXGSC-UHFFFAOYSA-N n-butyl-4,6-dichloro-1,3,5-triazin-2-amine Chemical compound CCCCNC1=NC(Cl)=NC(Cl)=N1 CIYATNIICRXGSC-UHFFFAOYSA-N 0.000 description 1
- ZRHAGDPKFFHVEY-UHFFFAOYSA-N n-phenyl-1,3,5-triazin-2-amine Chemical compound N=1C=NC=NC=1NC1=CC=CC=C1 ZRHAGDPKFFHVEY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4416—Metal complex azo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/095—Metal complex azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823202120 DE3202120A1 (de) | 1982-01-23 | 1982-01-23 | "wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu deren herstellung und ihre verwendng als farbstoffe" |
| IN66/CAL/83A IN157904B (en, 2012) | 1982-01-23 | 1983-01-17 | |
| DE8383100433T DE3363448D1 (en) | 1982-01-23 | 1983-01-19 | Water soluble copper complexes of disazo compounds, process for their preparation and their use as dyestuffs |
| EP83100433A EP0084849B1 (de) | 1982-01-23 | 1983-01-19 | Wasserlösliche Kupferkomplex-Disazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe |
| BR8300264A BR8300264A (pt) | 1982-01-23 | 1983-01-19 | Compostos disazoicos de complexos de cobre processo para sua obtencao sua aplicacao e processo para o tingimento de material contendo grupos hidroxi e/ou carbonamida |
| AR83291919A AR242237A1 (es) | 1982-01-23 | 1983-01-21 | Compuestos disazoicos en complejo de cobre hidrosoluble, procedimientos para su preparacion y su empleo como colorantes. |
| KR1019830000232A KR910001701B1 (ko) | 1982-01-23 | 1983-01-21 | 수용성 구리 디스아조 착화합물의 제조방법. |
| CS83432A CS233744B2 (en) | 1982-01-23 | 1983-01-21 | Processing of water soluble complexes of copper and disazocompounds |
| JP58008098A JPS58129063A (ja) | 1982-01-23 | 1983-01-22 | 水溶性銅錯体−ジスアゾ化合物及びこれを用いて染色する方法 |
| US06/702,687 US4939243A (en) | 1982-01-23 | 1985-02-20 | Water-soluble copper complex disazo compounds containg a chloro triazinylamino group and a group of the vinylsulfone series as fiber-reactive groups and their dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823202120 DE3202120A1 (de) | 1982-01-23 | 1982-01-23 | "wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu deren herstellung und ihre verwendng als farbstoffe" |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3202120A1 true DE3202120A1 (de) | 1983-07-28 |
Family
ID=6153760
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823202120 Withdrawn DE3202120A1 (de) | 1982-01-23 | 1982-01-23 | "wasserloesliche kupferkomplex-disazoverbindungen, verfahren zu deren herstellung und ihre verwendng als farbstoffe" |
| DE8383100433T Expired DE3363448D1 (en) | 1982-01-23 | 1983-01-19 | Water soluble copper complexes of disazo compounds, process for their preparation and their use as dyestuffs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383100433T Expired DE3363448D1 (en) | 1982-01-23 | 1983-01-19 | Water soluble copper complexes of disazo compounds, process for their preparation and their use as dyestuffs |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4939243A (en, 2012) |
| EP (1) | EP0084849B1 (en, 2012) |
| JP (1) | JPS58129063A (en, 2012) |
| KR (1) | KR910001701B1 (en, 2012) |
| AR (1) | AR242237A1 (en, 2012) |
| BR (1) | BR8300264A (en, 2012) |
| CS (1) | CS233744B2 (en, 2012) |
| DE (2) | DE3202120A1 (en, 2012) |
| IN (1) | IN157904B (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713082A (en) * | 1984-08-30 | 1987-12-15 | Ciba-Geigy Corporation | Process for dyeing or printing textile fibre materials with reactive dye containing vinyl sulfonyl-type group and chloro-triazinyl amino group |
| WO1994004515A1 (en) * | 1992-08-12 | 1994-03-03 | Sandoz Ltd | Method of increasing the spf rating and compounds suitable for increasing the spf rating of fibre or fabric |
| GB2315276A (en) * | 1996-07-11 | 1998-01-28 | Sumitomo Chemical Co | Disazo and trisazo compounds and method for dyeing or textile printing fibre material using the same |
| WO2003104335A1 (de) * | 2002-06-11 | 2003-12-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche faserreaktive disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwndung |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5233026A (en) * | 1984-09-26 | 1993-08-03 | Ciba-Geigy Corporation | Azo dyes containing chloro-s-triazine and vinylsulfonyl type fiber-reactive groups |
| JPS61138824A (ja) * | 1984-12-10 | 1986-06-26 | Toyota Motor Corp | 多気筒内燃機関の吸気管長可変式吸気装置 |
| JPS61149519A (ja) * | 1984-12-21 | 1986-07-08 | Nissan Motor Co Ltd | 多気筒内燃機関の吸気路装置 |
| TW224123B (en, 2012) * | 1991-11-08 | 1994-05-21 | Hoechst Ag | |
| TW411357B (en) * | 1994-11-17 | 2000-11-11 | Ciba Sc Holding Ag | Reactive azo dyes and their preparation |
| CA2483933A1 (en) * | 2002-04-27 | 2003-11-13 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Water-soluble fiber-reactive dyes, preparation thereof and use thereof |
| ATE343613T1 (de) * | 2002-09-26 | 2006-11-15 | Ilford Imaging Ch Gmbh | Kupferkomplex-monoazofarbstoffe, deren herstellung und verwendung |
| EP2904142A1 (en) | 2012-06-18 | 2015-08-12 | DyStar Colours Distribution GmbH | Reactive dyes and their metal complexes, process for the production thereof and their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3019936A1 (de) * | 1980-05-24 | 1981-12-03 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche farbige verbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| DE3019960A1 (de) * | 1980-05-24 | 1981-12-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zum faerben und bedrucken von hydroxy- und/oder carbonamidgruppen enthaltenden fasermaterialien |
-
1982
- 1982-01-23 DE DE19823202120 patent/DE3202120A1/de not_active Withdrawn
-
1983
- 1983-01-17 IN IN66/CAL/83A patent/IN157904B/en unknown
- 1983-01-19 EP EP83100433A patent/EP0084849B1/de not_active Expired
- 1983-01-19 BR BR8300264A patent/BR8300264A/pt not_active IP Right Cessation
- 1983-01-19 DE DE8383100433T patent/DE3363448D1/de not_active Expired
- 1983-01-21 KR KR1019830000232A patent/KR910001701B1/ko not_active Expired
- 1983-01-21 CS CS83432A patent/CS233744B2/cs unknown
- 1983-01-21 AR AR83291919A patent/AR242237A1/es active
- 1983-01-22 JP JP58008098A patent/JPS58129063A/ja active Granted
-
1985
- 1985-02-20 US US06/702,687 patent/US4939243A/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713082A (en) * | 1984-08-30 | 1987-12-15 | Ciba-Geigy Corporation | Process for dyeing or printing textile fibre materials with reactive dye containing vinyl sulfonyl-type group and chloro-triazinyl amino group |
| US5047514A (en) * | 1984-08-30 | 1991-09-10 | Ciba-Geigy Corporation | Bireactive primary disazo dyes containing 1-amino-8-hydroxynaphthalene-3,6 Disulfonic acid as coupling component |
| WO1994004515A1 (en) * | 1992-08-12 | 1994-03-03 | Sandoz Ltd | Method of increasing the spf rating and compounds suitable for increasing the spf rating of fibre or fabric |
| GB2315276A (en) * | 1996-07-11 | 1998-01-28 | Sumitomo Chemical Co | Disazo and trisazo compounds and method for dyeing or textile printing fibre material using the same |
| GB2315276B (en) * | 1996-07-11 | 1999-03-24 | Sumitomo Chemical Co | Polyazo compound and method for dyeing or textile printing fiber material using the same |
| US6015885A (en) * | 1996-07-11 | 2000-01-18 | Sumitomo Chemical Company, Limited | Polyazo compound and method for dyeing or textileprinting fiber material using the same |
| WO2003104335A1 (de) * | 2002-06-11 | 2003-12-18 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche faserreaktive disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwndung |
| US7132517B2 (en) | 2002-06-11 | 2006-11-07 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Water-soluble fiber-reactive disazo dyes, method for producing the same and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0084849B1 (de) | 1986-05-14 |
| DE3363448D1 (en) | 1986-06-19 |
| US4939243A (en) | 1990-07-03 |
| CS233744B2 (en) | 1985-03-14 |
| IN157904B (en, 2012) | 1986-07-19 |
| KR910001701B1 (ko) | 1991-03-19 |
| EP0084849A3 (en) | 1983-11-23 |
| JPS58129063A (ja) | 1983-08-01 |
| EP0084849A2 (de) | 1983-08-03 |
| AR242237A1 (es) | 1993-03-31 |
| JPH0424392B2 (en, 2012) | 1992-04-24 |
| BR8300264A (pt) | 1983-10-25 |
| KR840003259A (ko) | 1984-08-20 |
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| 8139 | Disposal/non-payment of the annual fee |