DE3030197A1 - Organische verbindungen, deren herstellung und verwendung - Google Patents
Organische verbindungen, deren herstellung und verwendungInfo
- Publication number
- DE3030197A1 DE3030197A1 DE19803030197 DE3030197A DE3030197A1 DE 3030197 A1 DE3030197 A1 DE 3030197A1 DE 19803030197 DE19803030197 DE 19803030197 DE 3030197 A DE3030197 A DE 3030197A DE 3030197 A1 DE3030197 A1 DE 3030197A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- parts
- hydrogen
- independently
- alkyl
- 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- Withdrawn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
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 238000004043 dyeing Methods 0.000 claims abstract description 26
- -1 disazo compound Chemical class 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 150000004696 coordination complex Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 239000010985 leather Substances 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 238000005859 coupling reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 18
- 230000008878 coupling Effects 0.000 claims description 18
- 238000010168 coupling process Methods 0.000 claims description 18
- 150000001879 copper Chemical class 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000002091 cationic group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004040 coloring Methods 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 229910052759 nickel Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 150000004982 aromatic amines Chemical group 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 12
- 125000003277 amino group Chemical group 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- 229920000742 Cotton Polymers 0.000 abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 2
- 239000000987 azo dye Substances 0.000 abstract 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052755 nonmetal Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001335 demethylating effect Effects 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- RCDMUNHSQCVVBJ-UHFFFAOYSA-N dibenzofuran-1-amine Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2N RCDMUNHSQCVVBJ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000011707 mineral Substances 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
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical group C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000001047 purple dye Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
-
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030197 DE3030197A1 (de) | 1980-08-09 | 1980-08-09 | Organische verbindungen, deren herstellung und verwendung |
| EP81810315A EP0051041B1 (en) | 1980-08-09 | 1981-08-04 | Basic or cationic sulphonic acid group-containing azo compounds, their synthesis and their use in dyeing substrates containing paper or cotton as well as dyestuff preparations thereof |
| AT81810315T ATE8792T1 (de) | 1980-08-09 | 1981-08-04 | Basische bzw. kationische sulfonsaeuregruppen enthaltende azoverbindungen, ihre herstellung und ihre verwendung als farbstoffe fuer substrate, die papier oder baumwolle enthalten, sowie daraus hergestellte farbstoffpraeparationen. |
| DE8181810315T DE3165229D1 (en) | 1980-08-09 | 1981-08-04 | Basic or cationic sulphonic acid group-containing azo compounds, their synthesis and their use in dyeing substrates containing paper or cotton as well as dyestuff preparations thereof |
| GB8123888A GB2082615B (en) | 1980-08-09 | 1981-08-05 | Improvements in or relating to organic compounds |
| ZA815452A ZA815452B (en) | 1980-08-09 | 1981-08-07 | Organic compounds |
| BR8105103A BR8105103A (pt) | 1980-08-09 | 1981-08-07 | Processo para preparar um composto e processo para tingir ou estampar substratos |
| ES504659A ES504659A0 (es) | 1980-08-09 | 1981-08-07 | Un procedimiento para la preparacion de compuestos de complejos metaliferos-mono-dis-o poliazoicos basicos o cationicos que contienen grupos acido sulfonico. |
| CA000383488A CA1177482A (en) | 1980-08-09 | 1981-08-07 | Organic compounds |
| JP56123177A JPS5753564A (en) | 1980-08-09 | 1981-08-07 | Azo compound |
| US06/409,111 US4594410A (en) | 1980-08-09 | 1982-08-18 | Azo compounds containing both sulfo groups and basic or cationic groups which compounds are in metal-free or 1:1 metal complex form |
| SG699/84A SG69984G (en) | 1980-08-09 | 1984-09-25 | Basic or cationic sulphonic acid group-containing azo compounds |
| HK5/85A HK585A (en) | 1980-08-09 | 1985-01-03 | Basic or cationic sulphonic acid group-containing azo compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030197 DE3030197A1 (de) | 1980-08-09 | 1980-08-09 | Organische verbindungen, deren herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3030197A1 true DE3030197A1 (de) | 1982-04-01 |
Family
ID=6109268
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803030197 Withdrawn DE3030197A1 (de) | 1980-08-09 | 1980-08-09 | Organische verbindungen, deren herstellung und verwendung |
| DE8181810315T Expired DE3165229D1 (en) | 1980-08-09 | 1981-08-04 | Basic or cationic sulphonic acid group-containing azo compounds, their synthesis and their use in dyeing substrates containing paper or cotton as well as dyestuff preparations thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181810315T Expired DE3165229D1 (en) | 1980-08-09 | 1981-08-04 | Basic or cationic sulphonic acid group-containing azo compounds, their synthesis and their use in dyeing substrates containing paper or cotton as well as dyestuff preparations thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4594410A (enExample) |
| EP (1) | EP0051041B1 (enExample) |
| JP (1) | JPS5753564A (enExample) |
| AT (1) | ATE8792T1 (enExample) |
| BR (1) | BR8105103A (enExample) |
| CA (1) | CA1177482A (enExample) |
| DE (2) | DE3030197A1 (enExample) |
| ES (1) | ES504659A0 (enExample) |
| GB (1) | GB2082615B (enExample) |
| HK (1) | HK585A (enExample) |
| SG (1) | SG69984G (enExample) |
| ZA (1) | ZA815452B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3340483A1 (de) * | 1982-11-22 | 1984-05-24 | Sandoz-Patent-GmbH, 7850 Lörrach | Sulfonsaeuregruppenfreie basische azoverbindungen, ihre herstellung und verwendung |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3133568A1 (de) * | 1981-08-25 | 1983-03-10 | Bayer Ag, 5090 Leverkusen | Wasserloesliche triazinverbindungen, ihre herstellung und ihre verwendung |
| EP0122458B1 (de) * | 1983-03-16 | 1989-01-04 | Ciba-Geigy Ag | Azoverbindungen |
| CH654320A5 (de) * | 1983-06-07 | 1986-02-14 | Ciba Geigy Ag | Azoverbindungen. |
| DE3440777C2 (de) * | 1983-11-14 | 1998-09-03 | Clariant Finance Bvi Ltd | Neue sulfonsäuregruppenhaltige, basische Azoverbindungen, deren Herstellung und Verwendung als Farbstoffe |
| CH668977A5 (de) * | 1985-08-19 | 1989-02-15 | Sandoz Ag | Basische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen. |
| CH671024A5 (enExample) * | 1986-04-17 | 1989-07-31 | Sandoz Ag | |
| CH672923A5 (enExample) * | 1986-06-07 | 1990-01-15 | Sandoz Ag | |
| JPH0696827B2 (ja) * | 1986-08-22 | 1994-11-30 | 日本化薬株式会社 | ジスアゾ化合物を用いる基材の染色法 |
| US4931067A (en) * | 1987-03-27 | 1990-06-05 | Sri International | Method or dyeing using phase change dyestuffs |
| JPH0742413B2 (ja) * | 1987-09-07 | 1995-05-10 | 日本化薬株式会社 | ジスアゾ化合物及びそれを用いる基材の染色法 |
| DE3815481A1 (de) * | 1988-05-06 | 1989-11-16 | Sandoz Ag | Sulfonsaeuregruppenfreie basische verbindung |
| JP2878692B2 (ja) * | 1988-09-13 | 1999-04-05 | 三菱化学株式会社 | インクジェット記録用記録液 |
| US5198022A (en) * | 1991-10-25 | 1993-03-30 | Lexmark International, Inc. | Waterfast dye and aqueous ink |
| US5631352A (en) * | 1994-06-20 | 1997-05-20 | Ciba-Geigy Corporation | Azodyes containing a bridge member based on diamino-substituted triazines |
| JP3423784B2 (ja) * | 1994-09-01 | 2003-07-07 | オリヱント化学工業株式会社 | 油性黒色インキ組成物 |
| EP0753542B1 (de) * | 1995-07-14 | 2000-02-09 | Bayer Ag | Polyazofarbstoffe |
| US5929215A (en) * | 1996-03-27 | 1999-07-27 | Clariant Finance (Bvi) Limited | Basic monoazo compounds |
| DE10015004A1 (de) | 2000-03-25 | 2001-09-27 | Clariant Gmbh | Schwarze Tris-Azo-Metall-Komplex-Farbstoffe |
| GB0113307D0 (en) * | 2001-06-01 | 2001-07-25 | Clariant Int Ltd | Organic compounds |
| DE10139826A1 (de) * | 2001-08-14 | 2003-02-27 | Clariant Gmbh | Verlackte Monoazopigmente auf der Basis von 1-Naphtholsulfonsäuren |
| GB0413557D0 (en) * | 2004-06-17 | 2004-07-21 | Avecia Ltd | Compounds |
| KR100844735B1 (ko) | 2004-08-06 | 2008-07-07 | 아사히 카세이 쿠라레 메디칼 가부시키가이샤 | 폴리술폰 혈액 투석기 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1211425A (fr) * | 1957-07-12 | 1960-03-16 | Sandoz Sa | Procédé pour transformer des colorants azoïques métallifères en dérivés aminés quaternaires |
| US3185676A (en) * | 1960-08-12 | 1965-05-25 | Gen Aniline & Film Corp | Method of azo dye chromation |
| GB958899A (en) * | 1961-07-03 | 1964-05-27 | Ici Ltd | Azo and anthraquinone dyestuffs containing quaternary ammonium groups |
| FR1370454A (fr) * | 1963-10-03 | 1964-08-21 | Hoechst Ag | Nouveaux colorants azoïques et leur préparation |
| CH564582A5 (en) * | 1970-09-03 | 1975-07-31 | Ciba Geigy Ag | Metal-contg monoazoic dyes - for collagen-contg material eg leather |
| DE2915323A1 (de) * | 1978-04-26 | 1979-11-08 | Sandoz Ag | Basische bzw. kationische, sulfonsaeuregruppenhaltige monoazo- oder disazoverbindungen |
| EP0014677B1 (de) * | 1979-02-02 | 1982-10-27 | Ciba-Geigy Ag | Basische Monoazofarbstoffe der Bis-benzthiazol-azobenzolreihe, Verfahren zu deren Herstellung sowie deren Verwendung zum Färben und Bedrucken von Textilmaterial, Papier, Leder und zur Bereitung von Tinten |
-
1980
- 1980-08-09 DE DE19803030197 patent/DE3030197A1/de not_active Withdrawn
-
1981
- 1981-08-04 DE DE8181810315T patent/DE3165229D1/de not_active Expired
- 1981-08-04 AT AT81810315T patent/ATE8792T1/de active
- 1981-08-04 EP EP81810315A patent/EP0051041B1/en not_active Expired
- 1981-08-05 GB GB8123888A patent/GB2082615B/en not_active Expired
- 1981-08-07 ES ES504659A patent/ES504659A0/es active Granted
- 1981-08-07 CA CA000383488A patent/CA1177482A/en not_active Expired
- 1981-08-07 ZA ZA815452A patent/ZA815452B/xx unknown
- 1981-08-07 JP JP56123177A patent/JPS5753564A/ja active Granted
- 1981-08-07 BR BR8105103A patent/BR8105103A/pt unknown
-
1982
- 1982-08-18 US US06/409,111 patent/US4594410A/en not_active Expired - Lifetime
-
1984
- 1984-09-25 SG SG699/84A patent/SG69984G/en unknown
-
1985
- 1985-01-03 HK HK5/85A patent/HK585A/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3340483A1 (de) * | 1982-11-22 | 1984-05-24 | Sandoz-Patent-GmbH, 7850 Lörrach | Sulfonsaeuregruppenfreie basische azoverbindungen, ihre herstellung und verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0051041B1 (en) | 1984-08-01 |
| HK585A (en) | 1985-01-11 |
| EP0051041A1 (en) | 1982-05-05 |
| GB2082615B (en) | 1984-08-08 |
| ES8302059A1 (es) | 1982-12-16 |
| JPH0470344B2 (enExample) | 1992-11-10 |
| ES504659A0 (es) | 1982-12-16 |
| GB2082615A (en) | 1982-03-10 |
| ZA815452B (en) | 1983-03-30 |
| ATE8792T1 (de) | 1984-08-15 |
| CA1177482A (en) | 1984-11-06 |
| SG69984G (en) | 1985-03-15 |
| JPS5753564A (en) | 1982-03-30 |
| DE3165229D1 (en) | 1984-09-06 |
| BR8105103A (pt) | 1982-04-27 |
| US4594410A (en) | 1986-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |