CA1064023A - 1:2 asymmetric cobalt complexes of monoazo dyestuffs - Google Patents
1:2 asymmetric cobalt complexes of monoazo dyestuffsInfo
- Publication number
- CA1064023A CA1064023A CA251,817A CA251817A CA1064023A CA 1064023 A CA1064023 A CA 1064023A CA 251817 A CA251817 A CA 251817A CA 1064023 A CA1064023 A CA 1064023A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- formula
- alkyl
- methyl
- phenyl
- 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.)
- Expired
Links
- 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 title abstract description 6
- 150000001868 cobalt Chemical class 0.000 title abstract description 5
- -1 sulpho group Chemical group 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 238000004043 dyeing Methods 0.000 claims abstract description 10
- 150000003839 salts Chemical group 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000758 substrate Substances 0.000 claims abstract description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000000460 chlorine Chemical group 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 229910006069 SO3H Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 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 4
- 150000004700 cobalt complex Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 159000000000 sodium salts Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 150000001408 amides Chemical class 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 12
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
- 229950011260 betanaphthol Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 5
- 229940075566 naphthalene Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000001145 hydrido group Chemical group *[H] 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- ALNWQAFPXMGLTJ-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=C(O)C=C2C(NC(=O)C)=CC=CC2=C1 ALNWQAFPXMGLTJ-UHFFFAOYSA-N 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- WLNBMPZUVDTASE-HXIISURNSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H]([NH3+])[C@@H](O)[C@H](O)[C@H](O)CO WLNBMPZUVDTASE-HXIISURNSA-N 0.000 description 1
- JDPKCYMVSKDOGS-UHFFFAOYSA-N 1,4-dichloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=C(Cl)C2=C1 JDPKCYMVSKDOGS-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KQEHXDNJMPNSPU-UHFFFAOYSA-N 1-isocyanatonaphthalen-2-ol Chemical compound C1=CC=CC2=C(N=C=O)C(O)=CC=C21 KQEHXDNJMPNSPU-UHFFFAOYSA-N 0.000 description 1
- POWXVFIRWRUILN-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=C(CBr)C=C1 POWXVFIRWRUILN-UHFFFAOYSA-N 0.000 description 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
- VGBFBFRAJWOOKH-UHFFFAOYSA-N 2-aminonaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(N)=CC=C21 VGBFBFRAJWOOKH-UHFFFAOYSA-N 0.000 description 1
- XKUWJBFNHCCDOF-UHFFFAOYSA-N 2-anilinonaphthalene-1-carbaldehyde Chemical compound C1=CC2=CC=CC=C2C(C=O)=C1NC1=CC=CC=C1 XKUWJBFNHCCDOF-UHFFFAOYSA-N 0.000 description 1
- KBPHGUKTJKPERJ-UHFFFAOYSA-N 2-methoxyethanesulfonic acid Chemical compound COCCS(O)(=O)=O KBPHGUKTJKPERJ-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- ZSUDUDXOEGHEJR-UHFFFAOYSA-N 4-methylnaphthalen-1-ol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=C1 ZSUDUDXOEGHEJR-UHFFFAOYSA-N 0.000 description 1
- DQEYNDJBOZCUET-UHFFFAOYSA-N 6,6-diamino-2-methylcyclohexa-2,4-diene-1,1-diol Chemical compound NC1(C(C(=CC=C1)C)(O)O)N DQEYNDJBOZCUET-UHFFFAOYSA-N 0.000 description 1
- LPPJAEZVHLBOHA-UHFFFAOYSA-N C1=CC=CC=C1S(=O)(=O)O.NC1=C(C=CC(=C1)[N+](=O)[O-])O Chemical compound C1=CC=CC=C1S(=O)(=O)O.NC1=C(C=CC(=C1)[N+](=O)[O-])O LPPJAEZVHLBOHA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- 241000042812 Divales Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 101100364844 Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440) salL gene Proteins 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 229910000001 cobalt(II) carbonate Inorganic materials 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 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
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- KYWYRNURERYQDW-UHFFFAOYSA-N n-(2,6-dimethylphenyl)naphthalen-2-amine Chemical compound CC1=CC=CC(C)=C1NC1=CC=C(C=CC=C2)C2=C1 KYWYRNURERYQDW-UHFFFAOYSA-N 0.000 description 1
- AHEJURHRYJPYST-UHFFFAOYSA-N n-ethylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NCC)=CC=C21 AHEJURHRYJPYST-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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
- C09B45/14—Monoazo compounds
- C09B45/20—Monoazo compounds containing cobalt
-
- 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
- C09B45/48—Preparation from other complex metal compounds of azo dyes
- C09B45/487—Cobalt complexes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH581775A CH615210A5 (en, 2012) | 1975-05-06 | 1975-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064023A true CA1064023A (en) | 1979-10-09 |
Family
ID=4299783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,817A Expired CA1064023A (en) | 1975-05-06 | 1976-05-05 | 1:2 asymmetric cobalt complexes of monoazo dyestuffs |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4155903A (en, 2012) |
| JP (1) | JPS51133259A (en, 2012) |
| BE (1) | BE841482A (en, 2012) |
| BR (1) | BR7602767A (en, 2012) |
| CA (1) | CA1064023A (en, 2012) |
| CH (1) | CH615210A5 (en, 2012) |
| DE (1) | DE2618611A1 (en, 2012) |
| ES (1) | ES447573A1 (en, 2012) |
| FR (1) | FR2310390A1 (en, 2012) |
| GB (1) | GB1545911A (en, 2012) |
| IT (1) | IT1061029B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3514387C2 (de) * | 1984-04-27 | 2003-12-24 | Clariant Finance Bvi Ltd | 1:2-Metallkomplex-azoverbindungen, ihre Herstellung und Verwendung |
| US5283325A (en) * | 1984-04-27 | 1994-02-01 | Sandoz Ltd. | 1:2 chromium and cobalt complexes of monoazo compounds having further unsubstituted or substituted nitro-2-hydroxyphenyl diazo component radicals and 6- or 7-acyl-amino-1-hydroxy-3-sulfonaphthalene coupling component radicals |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906746A (en) * | 1959-09-29 | Metalliferous azo dyestuffs | ||
| GB781286A (en) * | 1952-10-24 | 1957-08-14 | Ciba Ltd | Manufacture of new cobaltiferous azo-dyestuffs |
| US3005813A (en) * | 1953-05-22 | 1961-10-24 | Ciba Ltd | Metalliferous azo-dyestuffs |
| FR1101047A (fr) * | 1953-05-22 | 1955-09-27 | Ciba Geigy | Colorants azoïques métallifères, leur préparation et leur emploi |
| CH319237A (de) * | 1953-09-08 | 1957-02-15 | Ciba Geigy | Verfahren zur Herstellung neuer kobalthaltiger Azofarbstoffe |
| CH476812A (de) * | 1966-05-06 | 1969-08-15 | Geigy Ag J R | Verfahren zur Herstellung schwermetallhaltiger Azofarbstoffe |
| CH541607A (de) * | 1970-10-28 | 1973-09-15 | Sandoz Ag | Verfahren zur Herstellung von 1:1-Kobaltkomplexverbindungen |
| AU465010B2 (en) * | 1970-10-28 | 1975-09-18 | Sandoz Patents Limited | Process forthe production of 2:1 cobalt complex compounds |
-
1975
- 1975-05-06 CH CH581775A patent/CH615210A5/de not_active IP Right Cessation
-
1976
- 1976-04-28 DE DE19762618611 patent/DE2618611A1/de active Pending
- 1976-04-30 US US05/681,966 patent/US4155903A/en not_active Expired - Lifetime
- 1976-05-03 GB GB17917/76A patent/GB1545911A/en not_active Expired
- 1976-05-04 ES ES447573A patent/ES447573A1/es not_active Expired
- 1976-05-04 BR BR2767/76A patent/BR7602767A/pt unknown
- 1976-05-04 JP JP51050051A patent/JPS51133259A/ja active Pending
- 1976-05-05 CA CA251,817A patent/CA1064023A/en not_active Expired
- 1976-05-05 BE BE166752A patent/BE841482A/xx unknown
- 1976-05-06 IT IT23038/76A patent/IT1061029B/it active
- 1976-05-06 FR FR7613541A patent/FR2310390A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1061029B (it) | 1982-10-20 |
| FR2310390B1 (en, 2012) | 1979-09-28 |
| FR2310390A1 (fr) | 1976-12-03 |
| BE841482A (fr) | 1976-11-05 |
| ES447573A1 (es) | 1977-07-01 |
| CH615210A5 (en, 2012) | 1980-01-15 |
| GB1545911A (en) | 1979-05-16 |
| DE2618611A1 (de) | 1976-11-18 |
| US4155903A (en) | 1979-05-22 |
| BR7602767A (pt) | 1976-11-09 |
| JPS51133259A (en) | 1976-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK279233B6 (sk) | Azofarbivá, spôsob ich výroby a ich použitie na fa | |
| DE2842640A1 (de) | Reaktivfarbstoffe | |
| EP0252508B1 (en) | Water soluble disazo colorant and dyeing method using the same | |
| US3050516A (en) | Monoazo dyestuffs of low solubility in water | |
| US5958086A (en) | Dye mixtures, process for their preparation and the use thereof | |
| CA1052374A (en) | Trisazo dyes | |
| GB2064571A (en) | Reactive disazo dyestuffs | |
| US3261826A (en) | Monoazo triazine containing dyestuffs | |
| US3042648A (en) | Composition comprising an acrylonitrile polymer and a 2,4-diamino-5-aryl-6-hydroxy pyrimidine dye | |
| CA1064023A (en) | 1:2 asymmetric cobalt complexes of monoazo dyestuffs | |
| US3232931A (en) | Fiber-reactive metal phthalocyanine dyes | |
| GB2219804A (en) | Reactive dyes with cyanodihalopyrimidyl and chlorotriazinyl groups | |
| US2576037A (en) | Sulfonyl fluorides of amino azo dyestuffs | |
| GB2057480A (en) | Organic compounds | |
| US3236860A (en) | Water-soluble phthalocyanine dyestuffs containing thiosulfuric acid groups | |
| CA1112640A (en) | Reactive dyestuffs | |
| US3875139A (en) | Heavy metal complexes of azo dyestuffs containing the residue of a 2-amino-3-hydroxypyridine | |
| Raghav et al. | Synthesis and application of 2-aminothiadiazole disperse dyes for nylon fabrics | |
| US3869440A (en) | Metal-complex azo dyestuffs containing a 5-substituted-2,3-dihydroxypyridine as coupling component | |
| US2964520A (en) | Water-insoluble dyestuffs of the monohalogeno-triazine-amino alkylene amino-azobenzene series | |
| US4001203A (en) | Heavy metal complexes of azo dyestuffs containing a heterocyclic diazo component and the residue of 5-halogeno-2,3-dihydrozypyridine as coupling component | |
| DE2141453A1 (de) | Azoverbindungen, deren Herstellung und Verwendung | |
| GB1578988A (en) | Mixtures of 1:2 cobalt complexes of azo dyes | |
| US3502642A (en) | Reactive copper-containing benzeneazonaphthalene dyes containing a trichloropyrimidine group | |
| US2263994A (en) | Disazo dyestuff |