CS196434B2 - Method of preparing azo dyes - Google Patents
Method of preparing azo dyes Download PDFInfo
- Publication number
- CS196434B2 CS196434B2 CS785876A CS587678A CS196434B2 CS 196434 B2 CS196434 B2 CS 196434B2 CS 785876 A CS785876 A CS 785876A CS 587678 A CS587678 A CS 587678A CS 196434 B2 CS196434 B2 CS 196434B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- group
- amino
- acid
- naphthalene
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 27
- 239000000975 dye Substances 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 39
- -1 amine compound Chemical class 0.000 claims description 38
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- 230000005494 condensation Effects 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 15
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- 238000005859 coupling reaction Methods 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 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 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910001385 heavy metal Chemical class 0.000 claims description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 5
- 230000000536 complexating effect Effects 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 230000020335 dealkylation Effects 0.000 claims description 2
- 238000006900 dealkylation reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- XPOGFACFBAZCSB-UHFFFAOYSA-N 2,4,6-tris(fluoromethyl)-1H-triazine Chemical compound FCN1NC(=CC(=N1)CF)CF XPOGFACFBAZCSB-UHFFFAOYSA-N 0.000 claims 1
- 241000947840 Alteromonadales Species 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 229940124447 delivery agent Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 8
- 239000007859 condensation product Substances 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 3
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 3
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-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
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MLHWJIBYLDMVLQ-UHFFFAOYSA-N 4-[(3-aminobenzoyl)amino]-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound NC1=CC=CC(C(=O)NC=2C3=C(O)C=C(C=C3C=C(C=2)S(O)(=O)=O)S(O)(=O)=O)=C1 MLHWJIBYLDMVLQ-UHFFFAOYSA-N 0.000 description 2
- DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 2
- ZCNCWYFISJTFHB-UHFFFAOYSA-N 4-hydroxy-7-(methylamino)naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC)=CC=C21 ZCNCWYFISJTFHB-UHFFFAOYSA-N 0.000 description 2
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 description 2
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 238000009835 boiling Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- BDMZDKDLMHGPKF-UHFFFAOYSA-N (3-amino-4-methylphenyl)urea Chemical group CC1=CC=C(NC(N)=O)C=C1N BDMZDKDLMHGPKF-UHFFFAOYSA-N 0.000 description 1
- ONZWNZGVZFLMNZ-UHFFFAOYSA-N 1-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C([NH3+])=C(S([O-])(=O)=O)C=CC2=C1 ONZWNZGVZFLMNZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IQJKWKCLTAGFED-UHFFFAOYSA-N 2-aminonaphthalene-1,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 IQJKWKCLTAGFED-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- FFYHKFWYYPMFPC-UHFFFAOYSA-N 3-(sulfonylamino)aniline Chemical compound NC1=CC=CC(N=S(=O)=O)=C1 FFYHKFWYYPMFPC-UHFFFAOYSA-N 0.000 description 1
- OBEQWTGDHGJFQR-UHFFFAOYSA-N 3-acetamido-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(NC(=O)C)=CC2=C1O OBEQWTGDHGJFQR-UHFFFAOYSA-N 0.000 description 1
- ZDFCTUISEBJBEQ-UHFFFAOYSA-N 3-amino-4-hydroxynaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=C(O)C(N)=CC(S(O)(=O)=O)=C21 ZDFCTUISEBJBEQ-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
- PLVWAYLEIGEBGW-UHFFFAOYSA-N 3-amino-8-hydroxynaphthalene-1,6-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC(S(O)(=O)=O)=C21 PLVWAYLEIGEBGW-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
- WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 description 1
- MHZZQJHAYDHFGH-UHFFFAOYSA-N 3-ethyl-n-methylaniline Chemical compound CCC1=CC=CC(NC)=C1 MHZZQJHAYDHFGH-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- VHMGQUBUABNQFK-UHFFFAOYSA-N 4,6-difluoro-n-methyl-n-phenyl-1,3,5-triazin-2-amine Chemical compound N=1C(F)=NC(F)=NC=1N(C)C1=CC=CC=C1 VHMGQUBUABNQFK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 1
- LXBDMUVQELXOKG-UHFFFAOYSA-N 4-hydroxy-5-[(4-nitrobenzoyl)amino]naphthalene-2,7-disulfonic acid Chemical compound C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 LXBDMUVQELXOKG-UHFFFAOYSA-N 0.000 description 1
- HKWPUUYEGGDLJF-UHFFFAOYSA-N 4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HKWPUUYEGGDLJF-UHFFFAOYSA-N 0.000 description 1
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YKVBYISUDGOVDM-UHFFFAOYSA-N 6-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NC(=O)C)=CC=C21 YKVBYISUDGOVDM-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
- ZBGXGVYIKJFNAT-UHFFFAOYSA-N 6-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=C(S(O)(=O)=O)C(N)=CC=C21 ZBGXGVYIKJFNAT-UHFFFAOYSA-N 0.000 description 1
- DXQHKRLJFRUIKF-UHFFFAOYSA-N 7-(ethylamino)-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NCC)=CC=C21 DXQHKRLJFRUIKF-UHFFFAOYSA-N 0.000 description 1
- KKAMNIDZQVXDJV-UHFFFAOYSA-N 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)C)=CC=C21 KKAMNIDZQVXDJV-UHFFFAOYSA-N 0.000 description 1
- NWYPJANFHLUNFH-UHFFFAOYSA-N 7-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=C(O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 NWYPJANFHLUNFH-UHFFFAOYSA-N 0.000 description 1
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
- CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 230000027326 copulation Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FBGJJTQNZVNEQU-UHFFFAOYSA-N n,3-dimethylaniline Chemical compound CNC1=CC=CC(C)=C1 FBGJJTQNZVNEQU-UHFFFAOYSA-N 0.000 description 1
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
- BIYQLXLSSLKTNE-UHFFFAOYSA-N n-(3-aminophenyl)-2-hydroxyacetamide Chemical compound NC1=CC=CC(NC(=O)CO)=C1 BIYQLXLSSLKTNE-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
- ALANUUFGKYEMNI-UHFFFAOYSA-N n-naphthalen-1-ylbenzamide Chemical group C=1C=CC2=CC=CC=C2C=1NC(=O)C1=CC=CC=C1 ALANUUFGKYEMNI-UHFFFAOYSA-N 0.000 description 1
- HYFMZOAPNQAXHU-UHFFFAOYSA-N naphthalene-1,7-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 HYFMZOAPNQAXHU-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C09B62/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU78115A LU78115A1 (de) | 1977-09-12 | 1977-09-12 | Azofarbstoffe,deren herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196434B2 true CS196434B2 (en) | 1980-03-31 |
Family
ID=19728694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS785876A CS196434B2 (en) | 1977-09-12 | 1978-09-12 | Method of preparing azo dyes |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4866162A (de) |
| JP (1) | JPS6018703B2 (de) |
| AU (1) | AU3977678A (de) |
| BE (1) | BE870356A (de) |
| BR (1) | BR7805897A (de) |
| CA (1) | CA1111025A (de) |
| CH (1) | CH635859A5 (de) |
| CS (1) | CS196434B2 (de) |
| DE (1) | DE2839209C2 (de) |
| ES (1) | ES473589A1 (de) |
| FR (1) | FR2402687A1 (de) |
| GB (1) | GB2003911B (de) |
| LU (1) | LU78115A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH641197A5 (de) | 1977-12-23 | 1984-02-15 | Sandoz Ag | Reaktive monoazofarbstoffe und verfahren zu deren herstellung. |
| DE2838608A1 (de) * | 1978-09-05 | 1980-03-20 | Bayer Ag | Azo-reaktivfarbstoffe |
| CH655735A5 (de) * | 1982-09-17 | 1986-05-15 | Sandoz Ag | Reaktive monoazoverbindungen. |
| DE3943286A1 (de) * | 1989-12-29 | 1991-07-04 | Hoechst Ag | Azoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstofe |
| GB9204905D0 (en) * | 1992-03-06 | 1992-04-22 | Ici Plc | Compositions and compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627749A (en) * | 1963-07-10 | 1971-12-14 | Geigy Ag J R | Mono-and disazo dyestuffs containing triazinylureylene groups |
| US4115378A (en) * | 1967-04-19 | 1978-09-19 | Bayer Aktiengesellschaft | Water soluble reactive axodyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule |
| DE1644208C3 (de) * | 1967-04-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe |
| US4128544A (en) * | 1971-08-16 | 1978-12-05 | Sandoz Ltd. | Copper complexes of substituted sulfophenyl-azo-phenyl-azo-naphthalene sulfonic acids containing a heterocyclic fiber-reactive group |
| GB1366097A (en) * | 1971-09-10 | 1974-09-11 | Ici Ltd | Reactive metallised azo dyestuffs |
| JPS5217826B2 (de) * | 1974-05-31 | 1977-05-18 | ||
| CH626650A5 (de) * | 1974-12-18 | 1981-11-30 | Ciba Geigy Ag | |
| GB1549820A (en) * | 1975-11-06 | 1979-08-08 | Ciba Geigy Ag | Fibre-reactive dyes process for their manufacture and use thereof |
| CH614969A5 (en) * | 1975-12-19 | 1979-12-28 | Ciba Geigy Ag | Process for preparing fibre-reactive azo dyes |
| DE2729240C2 (de) * | 1977-06-29 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Azo-Reaktivfarbstoffe |
-
1977
- 1977-09-12 LU LU78115A patent/LU78115A1/de unknown
-
1978
- 1978-07-20 CH CH784078A patent/CH635859A5/de not_active IP Right Cessation
- 1978-09-08 DE DE2839209A patent/DE2839209C2/de not_active Expired
- 1978-09-11 FR FR7826028A patent/FR2402687A1/fr active Granted
- 1978-09-11 ES ES473589A patent/ES473589A1/es not_active Expired
- 1978-09-11 BE BE190381A patent/BE870356A/xx not_active IP Right Cessation
- 1978-09-11 CA CA311,074A patent/CA1111025A/en not_active Expired
- 1978-09-11 BR BR7805897A patent/BR7805897A/pt unknown
- 1978-09-12 CS CS785876A patent/CS196434B2/cs unknown
- 1978-09-12 JP JP53111379A patent/JPS6018703B2/ja not_active Expired
- 1978-09-12 GB GB7836529A patent/GB2003911B/en not_active Expired
- 1978-09-12 AU AU39776/78A patent/AU3977678A/en active Pending
-
1986
- 1986-10-02 US US06/914,556 patent/US4866162A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2003911A (en) | 1979-03-21 |
| BR7805897A (pt) | 1979-05-02 |
| AU3977678A (en) | 1980-03-20 |
| FR2402687A1 (fr) | 1979-04-06 |
| US4866162A (en) | 1989-09-12 |
| GB2003911B (en) | 1982-04-07 |
| CA1111025A (en) | 1981-10-20 |
| DE2839209C2 (de) | 1986-07-24 |
| JPS5450529A (en) | 1979-04-20 |
| CH635859A5 (de) | 1983-04-29 |
| JPS6018703B2 (ja) | 1985-05-11 |
| ES473589A1 (es) | 1979-04-16 |
| BE870356A (fr) | 1979-03-12 |
| DE2839209A1 (de) | 1979-03-15 |
| LU78115A1 (de) | 1979-05-23 |
| FR2402687B1 (de) | 1980-09-05 |
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