CH639683A5 - Process for preparing new copper complexes of azo dyes - Google Patents
Process for preparing new copper complexes of azo dyes Download PDFInfo
- Publication number
- CH639683A5 CH639683A5 CH1493077A CH1493077A CH639683A5 CH 639683 A5 CH639683 A5 CH 639683A5 CH 1493077 A CH1493077 A CH 1493077A CH 1493077 A CH1493077 A CH 1493077A CH 639683 A5 CH639683 A5 CH 639683A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dyes
- methylsulfonyl
- pyrimidinyl
- chloro
- radical
- Prior art date
Links
- 150000001879 copper Chemical class 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 2
- 125000006389 halopyrimidinyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004957 naphthylene group Chemical group 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- -1 aliphatic radical Chemical class 0.000 description 89
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 4
- NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 3
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- YXYCPKOAGWDZKX-UHFFFAOYSA-N 2,4-difluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC=C(C(F)(F)F)C(F)=N1 YXYCPKOAGWDZKX-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- CVXIRTCLVZZRKV-UHFFFAOYSA-N 1,4-dichlorophthalazine-6-carbonyl chloride Chemical compound ClC1=NN=C(Cl)C2=CC(C(=O)Cl)=CC=C21 CVXIRTCLVZZRKV-UHFFFAOYSA-N 0.000 description 1
- ZZQYDYODFHABLC-UHFFFAOYSA-N 1-chloro-1,2,2-trifluorocyclobutane Chemical compound FC1(F)CCC1(F)Cl ZZQYDYODFHABLC-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- KESAPMAPWGLLQL-UHFFFAOYSA-N 2,2,3,3-tetrafluorocyclobutane-1-carbonyl chloride Chemical compound FC1(F)CC(C(Cl)=O)C1(F)F KESAPMAPWGLLQL-UHFFFAOYSA-N 0.000 description 1
- BCOSEZGCLGPUSL-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoyl chloride Chemical compound ClC(Cl)=C(Cl)C(Cl)=O BCOSEZGCLGPUSL-UHFFFAOYSA-N 0.000 description 1
- QRXNZLRJSQBDJD-UHFFFAOYSA-N 2,3,5-tris(methylsulfonyl)pyrazine Chemical compound CS(=O)(=O)C1=CN=C(S(C)(=O)=O)C(S(C)(=O)=O)=N1 QRXNZLRJSQBDJD-UHFFFAOYSA-N 0.000 description 1
- BYVKICLDZSJHAA-UHFFFAOYSA-N 2,3-dibromoquinoxaline-6-carbonyl bromide Chemical compound N1=C(Br)C(Br)=NC2=CC(C(=O)Br)=CC=C21 BYVKICLDZSJHAA-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- FYSHPROTETTWKB-UHFFFAOYSA-N 2,4,5,6-tetrabromopyrimidine Chemical compound BrC1=NC(Br)=C(Br)C(Br)=N1 FYSHPROTETTWKB-UHFFFAOYSA-N 0.000 description 1
- KZMWBUVUQLGBBP-UHFFFAOYSA-N 2,4,5,6-tetrafluoropyrimidine Chemical compound FC1=NC(F)=C(F)C(F)=N1 KZMWBUVUQLGBBP-UHFFFAOYSA-N 0.000 description 1
- OQNKONMCYMWUGP-UHFFFAOYSA-N 2,4,5,6-tetrakis(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=NC(S(C)(=O)=O)=C(S(C)(=O)=O)C(S(C)(=O)=O)=N1 OQNKONMCYMWUGP-UHFFFAOYSA-N 0.000 description 1
- BIMGULMREAFXSC-UHFFFAOYSA-N 2,4,5-trifluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1F BIMGULMREAFXSC-UHFFFAOYSA-N 0.000 description 1
- LYBDHGMSPQBSNW-UHFFFAOYSA-N 2,4,5-trifluoropyrimidine Chemical compound FC1=NC=C(F)C(F)=N1 LYBDHGMSPQBSNW-UHFFFAOYSA-N 0.000 description 1
- XJNDXSGINZSFDF-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=C(Cl)N=C(Cl)N=C1Cl XJNDXSGINZSFDF-UHFFFAOYSA-N 0.000 description 1
- LUOWQRCVEYJUJS-UHFFFAOYSA-N 2,4,6-trifluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(C(F)(F)F)C(F)=N1 LUOWQRCVEYJUJS-UHFFFAOYSA-N 0.000 description 1
- AZVALKSFVWAVOL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1F AZVALKSFVWAVOL-UHFFFAOYSA-N 0.000 description 1
- JOYWMWSTASJQHZ-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine-5-carbonitrile Chemical compound FC1=NC(F)=C(C#N)C(F)=N1 JOYWMWSTASJQHZ-UHFFFAOYSA-N 0.000 description 1
- VAOWDUICNHWGRL-UHFFFAOYSA-N 2,4,6-tris(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=CC(S(C)(=O)=O)=NC(S(C)(=O)=O)=N1 VAOWDUICNHWGRL-UHFFFAOYSA-N 0.000 description 1
- HICXVCLBOSYEAA-UHFFFAOYSA-N 2,4-bis(benzenesulfonyl)-5-chloro-6-methylpyrimidine Chemical compound ClC=1C(C)=NC(S(=O)(=O)C=2C=CC=CC=2)=NC=1S(=O)(=O)C1=CC=CC=C1 HICXVCLBOSYEAA-UHFFFAOYSA-N 0.000 description 1
- CVXWQOAPKWGRTD-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)pyrimidine-5-sulfonyl chloride Chemical compound CS(=O)(=O)C1=NC=C(S(Cl)(=O)=O)C(S(C)(=O)=O)=N1 CVXWQOAPKWGRTD-UHFFFAOYSA-N 0.000 description 1
- YWURJMDYDBXTLA-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)quinazoline Chemical compound C1=CC=CC2=NC(S(=O)(=O)C)=NC(S(C)(=O)=O)=C21 YWURJMDYDBXTLA-UHFFFAOYSA-N 0.000 description 1
- ASVUGJYHCBOWLZ-UHFFFAOYSA-N 2,4-bis(trichloromethylsulfonyl)quinoline Chemical compound C1=CC=CC2=NC(S(=O)(=O)C(Cl)(Cl)Cl)=CC(S(=O)(=O)C(Cl)(Cl)Cl)=C21 ASVUGJYHCBOWLZ-UHFFFAOYSA-N 0.000 description 1
- AOEHEEBFRCAFGC-UHFFFAOYSA-N 2,4-dibromopyrimidine Chemical compound BrC1=CC=NC(Br)=N1 AOEHEEBFRCAFGC-UHFFFAOYSA-N 0.000 description 1
- DZTIFMWYYHCREC-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=CN=C(Cl)N=C1Cl DZTIFMWYYHCREC-UHFFFAOYSA-N 0.000 description 1
- NIAMELKDNLLWRH-UHFFFAOYSA-N 2,4-difluoro-5-methylpyrimidine Chemical compound CC1=CN=C(F)N=C1F NIAMELKDNLLWRH-UHFFFAOYSA-N 0.000 description 1
- QYJOBZGPEJHODY-UHFFFAOYSA-N 2,4-difluoro-5-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=CN=C(F)N=C1F QYJOBZGPEJHODY-UHFFFAOYSA-N 0.000 description 1
- GIBOHPZCGYRPBS-UHFFFAOYSA-N 2,4-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=C(F)N=C1F GIBOHPZCGYRPBS-UHFFFAOYSA-N 0.000 description 1
- GJOGRJUICNPNSV-UHFFFAOYSA-N 2,4-difluoro-5-phenylpyrimidine Chemical compound FC1=NC(F)=NC=C1C1=CC=CC=C1 GJOGRJUICNPNSV-UHFFFAOYSA-N 0.000 description 1
- FKSSZHRRUUZKCM-UHFFFAOYSA-N 2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=CC(C(F)(F)F)=NC(F)=N1 FKSSZHRRUUZKCM-UHFFFAOYSA-N 0.000 description 1
- YKLOPWRWWFKUBX-UHFFFAOYSA-N 2,4-difluoro-6-methylpyrimidine Chemical compound CC1=CC(F)=NC(F)=N1 YKLOPWRWWFKUBX-UHFFFAOYSA-N 0.000 description 1
- ZCHHTEOFXSGDMW-UHFFFAOYSA-N 2,4-difluoro-6-phenylpyrimidine Chemical compound FC1=NC(F)=CC(C=2C=CC=CC=2)=N1 ZCHHTEOFXSGDMW-UHFFFAOYSA-N 0.000 description 1
- JZSYSXZDIQUOGP-UHFFFAOYSA-N 2,4-difluoropyrimidine Chemical compound FC1=CC=NC(F)=N1 JZSYSXZDIQUOGP-UHFFFAOYSA-N 0.000 description 1
- YSKSNCNLMXAQLP-UHFFFAOYSA-N 2,6-bis(methylsulfonyl)pyridine-4-carbonyl chloride Chemical compound CS(=O)(=O)C1=CC(C(Cl)=O)=CC(S(C)(=O)=O)=N1 YSKSNCNLMXAQLP-UHFFFAOYSA-N 0.000 description 1
- YZRMBOOBRWRVJU-UHFFFAOYSA-N 2,6-bis(methylsulfonyl)pyrimidine-4-carbonyl chloride Chemical compound CS(=O)(=O)C1=CC(C(Cl)=O)=NC(S(C)(=O)=O)=N1 YZRMBOOBRWRVJU-UHFFFAOYSA-N 0.000 description 1
- PLVFHLAXDQSLCL-UHFFFAOYSA-N 2,6-dichloro-1h-triazin-4-amine Chemical compound NC1=NN(Cl)NC(Cl)=C1 PLVFHLAXDQSLCL-UHFFFAOYSA-N 0.000 description 1
- VYLHZPZYNPDQBR-UHFFFAOYSA-N 2,6-dichloro-4-(4-methylphenyl)-1h-triazine-5-thiol Chemical compound C1=CC(C)=CC=C1C1=NN(Cl)NC(Cl)=C1S VYLHZPZYNPDQBR-UHFFFAOYSA-N 0.000 description 1
- AMBBZHXGKGNTMI-UHFFFAOYSA-N 2,6-dichloro-4-ethoxy-1h-triazine Chemical compound CCOC1=NN(Cl)NC(Cl)=C1 AMBBZHXGKGNTMI-UHFFFAOYSA-N 0.000 description 1
- NNZQKAANXSXDNP-UHFFFAOYSA-N 2,6-dichloro-4-ethylsulfanyl-1h-triazine Chemical compound CCSC1=NN(Cl)NC(Cl)=C1 NNZQKAANXSXDNP-UHFFFAOYSA-N 0.000 description 1
- IOXIFBCDVPDGJV-UHFFFAOYSA-N 2,6-dichloro-4-methoxy-1h-triazine Chemical compound COC1=NN(Cl)NC(Cl)=C1 IOXIFBCDVPDGJV-UHFFFAOYSA-N 0.000 description 1
- DLMSWGCJMRVWCD-UHFFFAOYSA-N 2,6-dichloro-4-phenoxy-1h-triazine Chemical compound ClN1NC(Cl)=CC(OC=2C=CC=CC=2)=N1 DLMSWGCJMRVWCD-UHFFFAOYSA-N 0.000 description 1
- BHAFVZAFEVCQGJ-UHFFFAOYSA-N 2,6-dichloro-4-phenylsulfanyl-1h-triazine Chemical compound ClN1NC(Cl)=CC(SC=2C=CC=CC=2)=N1 BHAFVZAFEVCQGJ-UHFFFAOYSA-N 0.000 description 1
- CTSJEGLSMYPRJK-UHFFFAOYSA-N 2,6-dichloro-n-methyl-1h-triazin-4-amine Chemical compound CNC1=NN(Cl)NC(Cl)=C1 CTSJEGLSMYPRJK-UHFFFAOYSA-N 0.000 description 1
- NUYJCMGJLNVOML-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NC(Cl)=N1 NUYJCMGJLNVOML-UHFFFAOYSA-N 0.000 description 1
- WFJGZGDYFGUMCA-UHFFFAOYSA-N 2,6-difluoropyrimidine-4-carbonitrile Chemical compound FC1=CC(C#N)=NC(F)=N1 WFJGZGDYFGUMCA-UHFFFAOYSA-N 0.000 description 1
- RGNFAGBIKYERMX-UHFFFAOYSA-N 2-(4,5-dichloro-6-methylpyrimidin-2-yl)sulfonylacetic acid Chemical compound CC1=NC(S(=O)(=O)CC(O)=O)=NC(Cl)=C1Cl RGNFAGBIKYERMX-UHFFFAOYSA-N 0.000 description 1
- IDDLHNUKISKRRT-UHFFFAOYSA-N 2-(4-chloro-6-methylpyrimidin-2-yl)sulfonylethanesulfonic acid Chemical compound CC1=CC(Cl)=NC(S(=O)(=O)CCS(O)(=O)=O)=N1 IDDLHNUKISKRRT-UHFFFAOYSA-N 0.000 description 1
- ILNFTPTWDOAAEV-UHFFFAOYSA-N 2-(4-chloropyrimidin-2-yl)sulfonylacetic acid Chemical compound OC(=O)CS(=O)(=O)C1=NC=CC(Cl)=N1 ILNFTPTWDOAAEV-UHFFFAOYSA-N 0.000 description 1
- FAUYZTIBIRCNPZ-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-dichloro-6-methylpyrimidine Chemical compound ClC1=C(Cl)C(C)=NC(S(=O)(=O)C=2C=CC=CC=2)=N1 FAUYZTIBIRCNPZ-UHFFFAOYSA-N 0.000 description 1
- IJXOQDQYOMRDSO-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-dichloropyrimidine Chemical compound N1=C(Cl)C(Cl)=CN=C1S(=O)(=O)C1=CC=CC=C1 IJXOQDQYOMRDSO-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LNTAMLBOBVSKGY-UHFFFAOYSA-N 2-[2-(carboxymethylsulfonyl)quinolin-4-yl]sulfonylacetic acid Chemical compound C1=CC=CC2=NC(S(=O)(=O)CC(=O)O)=CC(S(=O)(=O)CC(O)=O)=C21 LNTAMLBOBVSKGY-UHFFFAOYSA-N 0.000 description 1
- BYHVGQHIAFURIL-UHFFFAOYSA-N 2-chloroquinoxaline Chemical compound C1=CC=CC2=NC(Cl)=CN=C21 BYHVGQHIAFURIL-UHFFFAOYSA-N 0.000 description 1
- CTSAKABLTRMUQJ-UHFFFAOYSA-N 2-sulfonyl-3h-1,3-benzothiazole Chemical class C1=CC=C2SC(=S(=O)=O)NC2=C1 CTSAKABLTRMUQJ-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- CIOZSHPCPJZSOS-UHFFFAOYSA-N 3,6-bis(benzenesulfonyl)pyridazine Chemical compound C=1C=C(S(=O)(=O)C=2C=CC=CC=2)N=NC=1S(=O)(=O)C1=CC=CC=C1 CIOZSHPCPJZSOS-UHFFFAOYSA-N 0.000 description 1
- QTAGZDNCORZVNJ-UHFFFAOYSA-N 3,6-bis(trichloromethylsulfonyl)pyridazine Chemical compound ClC(Cl)(Cl)S(=O)(=O)C1=CC=C(S(=O)(=O)C(Cl)(Cl)Cl)N=N1 QTAGZDNCORZVNJ-UHFFFAOYSA-N 0.000 description 1
- QPZGKMLYCRNKCK-UHFFFAOYSA-N 3-(benzenesulfonyl)propanoyl chloride Chemical compound ClC(=O)CCS(=O)(=O)C1=CC=CC=C1 QPZGKMLYCRNKCK-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 239000000284 extract Substances 0.000 description 1
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- 238000000227 grinding Methods 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
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- USPGWRYCHDAJCB-UHFFFAOYSA-N methyl 2,4-difluoropyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(F)N=C1F USPGWRYCHDAJCB-UHFFFAOYSA-N 0.000 description 1
- YSEQKGHEMQCJCC-UHFFFAOYSA-N methyl 2,6-difluoropyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(F)=NC(F)=N1 YSEQKGHEMQCJCC-UHFFFAOYSA-N 0.000 description 1
- YIROBCYPXUTGAN-UHFFFAOYSA-N methyl 5-chloro-2,6-difluoropyrimidine-4-carboxylate Chemical compound COC(=O)C1=NC(F)=NC(F)=C1Cl YIROBCYPXUTGAN-UHFFFAOYSA-N 0.000 description 1
- FSQBCNBFHWRUGG-UHFFFAOYSA-N methyl 6-chloro-2-methylsulfonylpyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(Cl)=NC(S(C)(=O)=O)=N1 FSQBCNBFHWRUGG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- FKORGLNGEASTQE-UHFFFAOYSA-N naphthalene-1,3-disulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 FKORGLNGEASTQE-UHFFFAOYSA-N 0.000 description 1
- HEWDOWUUTBCVJP-UHFFFAOYSA-N naphthalene-1,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HEWDOWUUTBCVJP-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
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/012—Metal complex azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655625 DE2655625C2 (de) | 1976-12-08 | 1976-12-08 | Metallkomplexfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639683A5 true CH639683A5 (en) | 1983-11-30 |
Family
ID=5994998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1493077A CH639683A5 (en) | 1976-12-08 | 1977-12-06 | Process for preparing new copper complexes of azo dyes |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5372039A (enrdf_load_stackoverflow) |
| CH (1) | CH639683A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2655625C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2373588A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1555642A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2839562A1 (de) * | 1978-09-12 | 1980-03-27 | Bayer Ag | Faserreaktive azofarbstoffe |
| GB2270923B (en) * | 1992-09-24 | 1995-11-08 | Sandoz Ltd | Fibre-reactive monoazo copper complexes |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH473880A (de) * | 1960-01-28 | 1969-06-15 | Ciba Geigy | Verfahren zur Herstellung neuer Metallkomplexverbindungen von Monoazofarbstoffen |
| FR1277942A (fr) * | 1961-01-26 | 1961-12-01 | Geigy Ag J R | Nouveaux colorants azoïques réactifs et leur préparation |
| DE1444591A1 (de) * | 1962-02-02 | 1968-11-21 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von neuen Monoazofarbstoffen |
| FR1365389A (fr) * | 1962-05-15 | 1964-07-03 | Ici Ltd | Colorants azoïques et leur procédé de fabrication |
| FR1373060A (fr) * | 1963-07-19 | 1964-09-25 | Mitsubishi Chem Ind | Nouveaux colorants azoïques, leur préparation et leur utilisation |
| CH463660A (de) * | 1965-05-14 | 1968-10-15 | Sandoz Ag | Verfahren zur Herstellung kupferhaltiger Reaktivfarbstoffe |
| DE1644171A1 (de) * | 1966-09-10 | 1970-07-30 | Bayer Ag | Reaktivfarbstoffe und Verfahren zu deren Herstellung |
-
1976
- 1976-12-08 DE DE19762655625 patent/DE2655625C2/de not_active Expired
-
1977
- 1977-12-05 GB GB5049777A patent/GB1555642A/en not_active Expired
- 1977-12-06 CH CH1493077A patent/CH639683A5/de not_active IP Right Cessation
- 1977-12-06 JP JP14579077A patent/JPS5372039A/ja active Pending
- 1977-12-08 FR FR7737013A patent/FR2373588A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2373588B1 (enrdf_load_stackoverflow) | 1983-08-12 |
| DE2655625C2 (de) | 1986-04-10 |
| DE2655625A1 (de) | 1978-06-15 |
| GB1555642A (en) | 1979-11-14 |
| FR2373588A1 (fr) | 1978-07-07 |
| JPS5372039A (en) | 1978-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |