CH615192A5 - Process for the preparation of novel aromatic amines - Google Patents
Process for the preparation of novel aromatic amines Download PDFInfo
- Publication number
- CH615192A5 CH615192A5 CH61077A CH61077A CH615192A5 CH 615192 A5 CH615192 A5 CH 615192A5 CH 61077 A CH61077 A CH 61077A CH 61077 A CH61077 A CH 61077A CH 615192 A5 CH615192 A5 CH 615192A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- amino
- formula
- sulfonic acid
- naphthylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 32
- 150000004982 aromatic amines Chemical class 0.000 title description 22
- 238000002360 preparation method Methods 0.000 title description 8
- 238000010168 coupling process Methods 0.000 description 71
- 238000005859 coupling reaction Methods 0.000 description 71
- 239000002253 acid Substances 0.000 description 65
- 239000000975 dye Substances 0.000 description 64
- 230000008878 coupling Effects 0.000 description 60
- -1 2-sulfo-5-phosphonophenyl Chemical group 0.000 description 54
- 150000001412 amines Chemical class 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000725 suspension Substances 0.000 description 24
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 21
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
- 235000011114 ammonium hydroxide Nutrition 0.000 description 19
- 229920002678 cellulose Polymers 0.000 description 18
- 239000001913 cellulose Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 14
- 150000001989 diazonium salts Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 14
- ZKAHHUOASUXTHW-UHFFFAOYSA-N 2-amino-4-phosphonobenzenesulfonic acid Chemical compound NC1=CC(P(O)(O)=O)=CC=C1S(O)(=O)=O ZKAHHUOASUXTHW-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 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 description 13
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- MZZQBSHNCYWSTL-UHFFFAOYSA-N (3-aminophenyl)phosphonic acid Chemical compound NC1=CC=CC(P(O)(O)=O)=C1 MZZQBSHNCYWSTL-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 9
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 9
- 230000005484 gravity Effects 0.000 description 8
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000000987 azo dye Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- 238000006277 sulfonation reaction Methods 0.000 description 6
- 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 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 5
- 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 5
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 5
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 4
- 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
- PCGISRHGYLRXSR-UHFFFAOYSA-N 4-hydroxy-7-[(5-hydroxy-7-sulfonaphthalen-2-yl)carbamoylamino]naphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)NC=3C=C4C=C(C=C(C4=CC=3)O)S(O)(=O)=O)=CC=C21 PCGISRHGYLRXSR-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 3
- HQBJSEKQNRSDAZ-UHFFFAOYSA-N 2,6-dimethoxyaniline Chemical compound COC1=CC=CC(OC)=C1N HQBJSEKQNRSDAZ-UHFFFAOYSA-N 0.000 description 3
- GUJOVAGILWAUAP-UHFFFAOYSA-N 3-amino-2-methoxy-5-phosphonobenzenesulfonic acid Chemical compound COC1=C(N)C=C(P(O)(O)=O)C=C1S(O)(=O)=O GUJOVAGILWAUAP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000003047 N-acetyl group Chemical group 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- KYSQEYOQLJTLLO-UHFFFAOYSA-N (3-aminophenyl)methylphosphonic acid Chemical compound NC1=CC=CC(CP(O)(O)=O)=C1 KYSQEYOQLJTLLO-UHFFFAOYSA-N 0.000 description 2
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-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
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 2
- RPGKFFKUTVJVPY-UHFFFAOYSA-N 2-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(N)=C1 RPGKFFKUTVJVPY-UHFFFAOYSA-N 0.000 description 2
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 2
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 2
- HKJKONMZMPUGHJ-UHFFFAOYSA-N 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]-6-phenyldiazenylnaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=C(N=NC=3C=CC=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 HKJKONMZMPUGHJ-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 2
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 2
- TYCNXOAPQGVAQU-UHFFFAOYSA-N 5-oxo-1-(4-sulfophenyl)-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=C(S(O)(=O)=O)C=C1 TYCNXOAPQGVAQU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 2
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- CBFOGZZZUOQJAO-UHFFFAOYSA-N COC1=C(N)C=C(C=C1)OC.NC=1C(=CC=C(C1)C)C Chemical compound COC1=C(N)C=C(C=C1)OC.NC=1C(=CC=C(C1)C)C CBFOGZZZUOQJAO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 2
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical class OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UHCDKLNZOMPPFB-UHFFFAOYSA-N (2-amino-5-chlorophenyl)phosphonic acid Chemical compound NC1=CC=C(Cl)C=C1P(O)(O)=O UHCDKLNZOMPPFB-UHFFFAOYSA-N 0.000 description 1
- OCTQTMOZJRPHHQ-UHFFFAOYSA-N (3-amino-4-chlorophenyl)phosphonic acid Chemical compound NC1=CC(P(O)(O)=O)=CC=C1Cl OCTQTMOZJRPHHQ-UHFFFAOYSA-N 0.000 description 1
- ADEXNPNSGDGRGU-UHFFFAOYSA-N (3-amino-4-methoxyphenyl)phosphonic acid Chemical compound COC1=CC=C(P(O)(O)=O)C=C1N ADEXNPNSGDGRGU-UHFFFAOYSA-N 0.000 description 1
- WKSXTCKQVYDMGF-UHFFFAOYSA-N (3-amino-4-methylphenyl)phosphonic acid Chemical compound CC1=CC=C(P(O)(O)=O)C=C1N WKSXTCKQVYDMGF-UHFFFAOYSA-N 0.000 description 1
- BVLOPAOIDRBBCJ-UHFFFAOYSA-N (4-amino-2-bromophenyl)phosphonic acid Chemical compound NC1=CC=C(P(O)(O)=O)C(Br)=C1 BVLOPAOIDRBBCJ-UHFFFAOYSA-N 0.000 description 1
- GCHVOOCQLHLZHU-UHFFFAOYSA-N (4-amino-2-fluorophenyl)phosphonic acid Chemical compound NC1=CC=C(P(O)(O)=O)C(F)=C1 GCHVOOCQLHLZHU-UHFFFAOYSA-N 0.000 description 1
- HSWZHLXFZBRUOP-UHFFFAOYSA-N (4-amino-3-nitrophenyl)phosphonic acid Chemical compound NC1=CC=C(P(O)(O)=O)C=C1[N+]([O-])=O HSWZHLXFZBRUOP-UHFFFAOYSA-N 0.000 description 1
- OAOBMEMWHJWPNA-UHFFFAOYSA-N (4-aminophenyl)phosphonic acid Chemical compound NC1=CC=C(P(O)(O)=O)C=C1 OAOBMEMWHJWPNA-UHFFFAOYSA-N 0.000 description 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- YSNMMQRIPFUHAO-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carbonitrile Chemical compound CCN1C(O)=C(C#N)C(C)=CC1=O YSNMMQRIPFUHAO-UHFFFAOYSA-N 0.000 description 1
- RWBLSVPYDPODTR-UHFFFAOYSA-N 1-ethyl-6-hydroxy-4-methylpyridin-2-one Chemical compound CCN1C(O)=CC(C)=CC1=O RWBLSVPYDPODTR-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- KCEIVWKDBLAQKL-UHFFFAOYSA-N 2,5-dichloro-4-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl KCEIVWKDBLAQKL-UHFFFAOYSA-N 0.000 description 1
- NHXOVQUFJNKUFI-UHFFFAOYSA-N 2,5-dimethylaniline;2-methoxy-5-methylaniline Chemical compound CC1=CC=C(C)C(N)=C1.COC1=CC=C(C)C=C1N NHXOVQUFJNKUFI-UHFFFAOYSA-N 0.000 description 1
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- DJZKNOVUNYPPEE-UHFFFAOYSA-N tetradecane-1,4,11,14-tetracarboxamide Chemical compound NC(=O)CCCC(C(N)=O)CCCCCCC(C(N)=O)CCCC(N)=O DJZKNOVUNYPPEE-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/007—Dyestuffs containing phosphonic or phosphinic acid groups and derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
-
- 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
- C09B31/02—Disazo dyes
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- 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
- C09B33/02—Disazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups
- C09B45/36—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups by oxidation of hydrogen in o'-position
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB217076A GB1512924A (en) | 1976-01-20 | 1976-01-20 | Aminobenzene phosphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615192A5 true CH615192A5 (en) | 1980-01-15 |
Family
ID=9734817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH61077A CH615192A5 (en) | 1976-01-20 | 1977-01-18 | Process for the preparation of novel aromatic amines |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5289129A (enExample) |
| AR (1) | AR213108A1 (enExample) |
| BR (1) | BR7700315A (enExample) |
| CH (1) | CH615192A5 (enExample) |
| CS (1) | CS196340B2 (enExample) |
| DD (1) | DD128685A1 (enExample) |
| DE (1) | DE2702263A1 (enExample) |
| ES (2) | ES455186A1 (enExample) |
| FR (1) | FR2338977A1 (enExample) |
| GB (1) | GB1512924A (enExample) |
| IT (1) | IT1133909B (enExample) |
| PL (1) | PL195340A1 (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2221498B1 (enExample) * | 1972-12-15 | 1976-02-13 | Ugine Kulhmann Fr | |
| IT1060240B (it) * | 1975-05-07 | 1982-07-10 | Ici Ltd | Coloratni monoazoici |
-
1976
- 1976-01-20 GB GB217076A patent/GB1512924A/en not_active Expired
- 1976-12-20 AR AR26593576A patent/AR213108A1/es active
- 1976-12-30 FR FR7639671A patent/FR2338977A1/fr active Granted
- 1976-12-31 IT IT3106576A patent/IT1133909B/it active
-
1977
- 1977-01-15 PL PL19534077A patent/PL195340A1/xx not_active IP Right Cessation
- 1977-01-18 CH CH61077A patent/CH615192A5/de not_active IP Right Cessation
- 1977-01-18 BR BR7700315A patent/BR7700315A/pt unknown
- 1977-01-18 DD DD19699277A patent/DD128685A1/xx unknown
- 1977-01-19 CS CS36577A patent/CS196340B2/cs unknown
- 1977-01-20 ES ES455186A patent/ES455186A1/es not_active Expired
- 1977-01-20 JP JP535877A patent/JPS5289129A/ja active Pending
- 1977-01-20 ES ES455187A patent/ES455187A1/es not_active Expired
- 1977-01-20 DE DE19772702263 patent/DE2702263A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2338977A1 (fr) | 1977-08-19 |
| DE2702263A1 (de) | 1977-07-21 |
| DD128685A1 (de) | 1977-12-07 |
| JPS5289129A (ja) | 1977-07-26 |
| AR213108A1 (es) | 1978-12-15 |
| ES455187A1 (es) | 1977-12-16 |
| CS196340B2 (en) | 1980-03-31 |
| GB1512924A (en) | 1978-06-01 |
| BR7700315A (pt) | 1977-09-20 |
| FR2338977B1 (enExample) | 1980-10-24 |
| IT1133909B (it) | 1986-07-24 |
| PL195340A1 (pl) | 1979-05-07 |
| ES455186A1 (es) | 1977-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |