CH618725A5 - - Google Patents
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- Publication number
- CH618725A5 CH618725A5 CH620677A CH620677A CH618725A5 CH 618725 A5 CH618725 A5 CH 618725A5 CH 620677 A CH620677 A CH 620677A CH 620677 A CH620677 A CH 620677A CH 618725 A5 CH618725 A5 CH 618725A5
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- sulfonic acid
- hydroxy
- formula
- naphthalene
- Prior art date
Links
- 238000005859 coupling reaction Methods 0.000 claims description 75
- 230000008878 coupling Effects 0.000 claims description 72
- 238000010168 coupling process Methods 0.000 claims description 72
- 239000000975 dye Substances 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 59
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 23
- 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 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- VNMGVBPCESRCOG-UHFFFAOYSA-N OC(=O)ClS(O)(=O)=O Chemical compound OC(=O)ClS(O)(=O)=O VNMGVBPCESRCOG-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 claims description 2
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 2
- -1 heterocyclic radical Chemical class 0.000 description 50
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 46
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 29
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 20
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 18
- 229940018563 3-aminophenol Drugs 0.000 description 18
- 229920000742 Cotton Polymers 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004043 dyeing Methods 0.000 description 12
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 10
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 8
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 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 7
- KUKUFBGWRFXTAD-UHFFFAOYSA-N 2-(3-amino-4-methylanilino)acetic acid Chemical compound CC1=CC=C(NCC(O)=O)C=C1N KUKUFBGWRFXTAD-UHFFFAOYSA-N 0.000 description 6
- IPQWXJDRMKGSFI-UHFFFAOYSA-N 3,5-diamino-4-methylbenzenesulfonic acid Chemical compound CC1=C(N)C=C(S(O)(=O)=O)C=C1N IPQWXJDRMKGSFI-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- MXUKTFBCWISLPC-UHFFFAOYSA-N 2-(3-aminoanilino)acetic acid Chemical compound NC1=CC=CC(NCC(O)=O)=C1 MXUKTFBCWISLPC-UHFFFAOYSA-N 0.000 description 4
- BEXBJUKRZILANI-UHFFFAOYSA-N 2-(4-aminophenyl)-4-methyl-1h-benzimidazol-5-amine Chemical compound N=1C=2C(C)=C(N)C=CC=2NC=1C1=CC=C(N)C=C1 BEXBJUKRZILANI-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 239000004627 regenerated cellulose Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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 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 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 244000172533 Viola sororia Species 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- XAQCYASNAMYTQA-UHFFFAOYSA-N 2,4-diamino-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1N XAQCYASNAMYTQA-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
- WDCBRAZWDCIVSN-UHFFFAOYSA-N 2-(3-amino-4-methylanilino)ethanol Chemical compound CC1=CC=C(NCCO)C=C1N WDCBRAZWDCIVSN-UHFFFAOYSA-N 0.000 description 2
- ZTNLMELMADJSAH-UHFFFAOYSA-N 2-(3-aminoanilino)ethanol Chemical compound NC1=CC=CC(NCCO)=C1 ZTNLMELMADJSAH-UHFFFAOYSA-N 0.000 description 2
- JOTHLSOQKMTNIB-UHFFFAOYSA-N 2-(4-aminophenyl)-6-chloro-1h-benzimidazol-5-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC(N)=C(Cl)C=C2N1 JOTHLSOQKMTNIB-UHFFFAOYSA-N 0.000 description 2
- DEDPGHOISADEIE-UHFFFAOYSA-N 2-(4-aminophenyl)-6-methyl-1h-benzimidazol-5-amine Chemical compound N=1C=2C=C(N)C(C)=CC=2NC=1C1=CC=C(N)C=C1 DEDPGHOISADEIE-UHFFFAOYSA-N 0.000 description 2
- NZRATORTMDZJPL-UHFFFAOYSA-N 2-(4-aminophenyl)-7-chloro-3h-benzimidazol-5-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=C(Cl)C=C(N)C=C2N1 NZRATORTMDZJPL-UHFFFAOYSA-N 0.000 description 2
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 2
- PIJNMVNHBRSTEJ-UHFFFAOYSA-N 3,5-diamino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(N)=C1Cl PIJNMVNHBRSTEJ-UHFFFAOYSA-N 0.000 description 2
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical class C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 2
- IOGJZJBDZNUKKC-UHFFFAOYSA-N NC(C)NC1=CC(=CC=C1)C(=O)O Chemical compound NC(C)NC1=CC(=CC=C1)C(=O)O IOGJZJBDZNUKKC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 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 2
- 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 2
- 229920002647 polyamide Polymers 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 238000003419 tautomerization reaction Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- PJMARVPGHIRWCF-UHFFFAOYSA-N (2,3-diaminophenyl)methanesulfonic acid Chemical compound NC1=CC=CC(CS(O)(=O)=O)=C1N PJMARVPGHIRWCF-UHFFFAOYSA-N 0.000 description 1
- XQOKCFAOVZLPJL-UHFFFAOYSA-N (3-aminoanilino)methanesulfonic acid Chemical compound NC1=CC=CC(NCS(O)(=O)=O)=C1 XQOKCFAOVZLPJL-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- FIYNNIMRGIRYEO-UHFFFAOYSA-N 2-(2,3-diaminophenyl)acetic acid Chemical compound NC1=CC=CC(CC(O)=O)=C1N FIYNNIMRGIRYEO-UHFFFAOYSA-N 0.000 description 1
- UPGPODWXZVLKMW-UHFFFAOYSA-N 2-(2,3-diaminophenyl)ethanesulfonic acid Chemical compound NC1=C(C(=CC=C1)CCS(=O)(=O)O)N UPGPODWXZVLKMW-UHFFFAOYSA-N 0.000 description 1
- GRYIZJSFTAZEFE-UHFFFAOYSA-N 2-(4-aminophenyl)-1-benzylbenzimidazol-5-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC(N)=CC=C2N1CC1=CC=CC=C1 GRYIZJSFTAZEFE-UHFFFAOYSA-N 0.000 description 1
- XAFOTXWPFVZQAZ-UHFFFAOYSA-N 2-(4-aminophenyl)-3h-benzimidazol-5-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=C(N)C=C2N1 XAFOTXWPFVZQAZ-UHFFFAOYSA-N 0.000 description 1
- LZJIZLLZXZKCQM-UHFFFAOYSA-N 2-(4-aminophenyl)-5-chloro-1,3-benzothiazol-6-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC(Cl)=C(N)C=C2S1 LZJIZLLZXZKCQM-UHFFFAOYSA-N 0.000 description 1
- QNMQGTOTZBDFPY-UHFFFAOYSA-N 2-(4-aminophenyl)-6-ethoxy-3h-benzimidazol-5-amine Chemical compound N1C=2C=C(N)C(OCC)=CC=2N=C1C1=CC=C(N)C=C1 QNMQGTOTZBDFPY-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
- GWMSUPQGLMRCRR-UHFFFAOYSA-N 2-amino-4-(sulfomethylamino)benzenesulfonic acid Chemical compound NC1=CC(NCS(O)(=O)=O)=CC=C1S(O)(=O)=O GWMSUPQGLMRCRR-UHFFFAOYSA-N 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- GYFZMCLUPHXUDV-UHFFFAOYSA-N 2-ethoxy-5-methylaniline Chemical compound CCOC1=CC=C(C)C=C1N GYFZMCLUPHXUDV-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 1
- BFTCOOLIWWXDEJ-UHFFFAOYSA-N 4-(2-aminoethylamino)phenol Chemical compound NCCNC1=CC=C(O)C=C1 BFTCOOLIWWXDEJ-UHFFFAOYSA-N 0.000 description 1
- ZWUBBMDHSZDNTA-UHFFFAOYSA-N 4-Chloro-meta-phenylenediamine Chemical compound NC1=CC=C(Cl)C(N)=C1 ZWUBBMDHSZDNTA-UHFFFAOYSA-N 0.000 description 1
- FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 1
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 1
- LMGWHMKXSXDWRB-UHFFFAOYSA-N 4-propylbenzene-1,3-diamine Chemical compound CCCC1=CC=C(N)C=C1N LMGWHMKXSXDWRB-UHFFFAOYSA-N 0.000 description 1
- PVQRMRDCXXFGHR-UHFFFAOYSA-N 5-acetamido-3-amino-2-methylbenzenesulfonic acid Chemical compound CC(=O)NC1=CC(N)=C(C)C(S(O)(=O)=O)=C1 PVQRMRDCXXFGHR-UHFFFAOYSA-N 0.000 description 1
- JSCNCRWPXOTDDZ-UHFFFAOYSA-N 5-amino-2-chlorophenol Chemical compound NC1=CC=C(Cl)C(O)=C1 JSCNCRWPXOTDDZ-UHFFFAOYSA-N 0.000 description 1
- BAUHYBAZPJDNIW-UHFFFAOYSA-N 8,8-diamino-7H-naphthalen-1-ol Chemical compound NC1(CC=CC2=CC=CC(=C12)O)N BAUHYBAZPJDNIW-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- HINJYFLLUNPFSO-UHFFFAOYSA-N COC1=C(N)C=C(C=C1)C.COC1=C(N)C=C(C=C1)OC Chemical compound COC1=C(N)C=C(C=C1)C.COC1=C(N)C=C(C=C1)OC HINJYFLLUNPFSO-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZHBSYDBFOZLBFI-UHFFFAOYSA-N NC1=CC2=CC=C(C=C2C=C1S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=C(C=CC=C2C=C1)S(=O)(=O)O.NC1=CC2=CC(=CC=C2C=C1)S(=O)(=O)O.NC1=CC2=CC=C(C=C2C=C1)S(=O)(=O)O.NC1=CC=2C=CC=C(C2C=C1)S(=O)(=O)O Chemical compound NC1=CC2=CC=C(C=C2C=C1S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=C(C=CC=C2C=C1)S(=O)(=O)O.NC1=CC2=CC(=CC=C2C=C1)S(=O)(=O)O.NC1=CC2=CC=C(C=C2C=C1)S(=O)(=O)O.NC1=CC=2C=CC=C(C2C=C1)S(=O)(=O)O ZHBSYDBFOZLBFI-UHFFFAOYSA-N 0.000 description 1
- SSXYLPGYDLBHNK-UHFFFAOYSA-N NC1=CC=C(C2=CC=CC(=C12)O)S(=O)(=O)O.NC1=CC=CC=2C(=CC(=CC12)O)S(=O)(=O)O.NC1=CC=CC2=C(C=C(C=C12)S(=O)(=O)O)O Chemical compound NC1=CC=C(C2=CC=CC(=C12)O)S(=O)(=O)O.NC1=CC=CC=2C(=CC(=CC12)O)S(=O)(=O)O.NC1=CC=CC2=C(C=C(C=C12)S(=O)(=O)O)O SSXYLPGYDLBHNK-UHFFFAOYSA-N 0.000 description 1
- OHPDBAFACVWHHK-UHFFFAOYSA-N NC1=CC=C(C=C1)C=1OC2=C(N1)C=CC(=C2)N.NC2=CC=C(C=C2)C=2OC1=C(N2)C=C(C=C1)N Chemical compound NC1=CC=C(C=C1)C=1OC2=C(N1)C=CC(=C2)N.NC2=CC=C(C=C2)C=2OC1=C(N2)C=C(C=C1)N OHPDBAFACVWHHK-UHFFFAOYSA-N 0.000 description 1
- ZIMBXJDZRYGLAK-UHFFFAOYSA-N NC1=CC=C(C=C1)C=1SC2=C(N1)C=CC(=C2)N.NC2=CC=C(C=C2)C=2SC1=C(N2)C=C(C=C1)N Chemical compound NC1=CC=C(C=C1)C=1SC2=C(N1)C=CC(=C2)N.NC2=CC=C(C=C2)C=2SC1=C(N2)C=C(C=C1)N ZIMBXJDZRYGLAK-UHFFFAOYSA-N 0.000 description 1
- VHFSGALPSMARHD-UHFFFAOYSA-N NC1=CC=CC2=CC(=CC=C12)S(=O)(=O)O.NC1=CC(=CC=C1)N Chemical compound NC1=CC=CC2=CC(=CC=C12)S(=O)(=O)O.NC1=CC(=CC=C1)N VHFSGALPSMARHD-UHFFFAOYSA-N 0.000 description 1
- 244000154870 Viola adunca Species 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- DOTXPLDMWBZANU-UHFFFAOYSA-N n-(3-amino-4-ethylphenyl)acetamide Chemical compound CCC1=CC=C(NC(C)=O)C=C1N DOTXPLDMWBZANU-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
- DRXFARCOYOPZDW-UHFFFAOYSA-N n-(3-aminophenyl)butanamide Chemical compound CCCC(=O)NC1=CC=CC(N)=C1 DRXFARCOYOPZDW-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
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- D06P1/04—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 not containing metal
- D06P1/06—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 not containing metal containing acid groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
- C09B35/376—D is a heterocyclic compound
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762622303 DE2622303A1 (de) | 1976-05-19 | 1976-05-19 | Loesliche trisazofarbstoffe, ihre herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618725A5 true CH618725A5 (en, 2012) | 1980-08-15 |
Family
ID=5978409
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH620777A CH618726A5 (en, 2012) | 1976-05-19 | 1977-05-18 | |
| CH620677A CH618725A5 (en, 2012) | 1976-05-19 | 1977-05-18 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH620777A CH618726A5 (en, 2012) | 1976-05-19 | 1977-05-18 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4144231A (en, 2012) |
| JP (2) | JPS52140540A (en, 2012) |
| BE (2) | BE854820A (en, 2012) |
| BR (2) | BR7703199A (en, 2012) |
| CH (2) | CH618726A5 (en, 2012) |
| DE (1) | DE2622303A1 (en, 2012) |
| FR (2) | FR2352039A1 (en, 2012) |
| GB (2) | GB1543453A (en, 2012) |
| IN (2) | IN146336B (en, 2012) |
| IT (1) | IT1143663B (en, 2012) |
| NL (2) | NL7705269A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0169808A3 (en) * | 1984-07-24 | 1988-12-21 | Ciba-Geigy Ag | Uv-absorber compounds, method for their preparation and their use as image dyes in photographic materials for the silver dye-bleaching process |
| DE3743527A1 (de) * | 1987-12-22 | 1989-07-06 | Cassella Ag | Wasserloesliche schwarze trisazofarbstoffe |
| GB0210824D0 (en) * | 2002-05-11 | 2002-06-19 | Avecia Ltd | Compounds |
| GB0226710D0 (en) * | 2002-11-15 | 2002-12-24 | Avecia Ltd | Inks |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424462A1 (de) * | 1974-05-20 | 1975-12-11 | Cassella Farbwerke Mainkur Ag | Loesliche trisazofarbstoffe, ihre herstellung und verwendung |
-
1976
- 1976-05-19 DE DE19762622303 patent/DE2622303A1/de not_active Ceased
-
1977
- 1977-05-10 US US05/795,435 patent/US4144231A/en not_active Expired - Lifetime
- 1977-05-10 US US05/795,434 patent/US4144230A/en not_active Expired - Lifetime
- 1977-05-12 NL NL7705269A patent/NL7705269A/xx unknown
- 1977-05-12 NL NL7705270A patent/NL7705270A/xx not_active Application Discontinuation
- 1977-05-16 IN IN730/CAL/77A patent/IN146336B/en unknown
- 1977-05-16 IN IN729/CAL/77A patent/IN146335B/en unknown
- 1977-05-18 BE BE177729A patent/BE854820A/xx unknown
- 1977-05-18 BR BR7703199A patent/BR7703199A/pt unknown
- 1977-05-18 GB GB20915/77A patent/GB1543453A/en not_active Expired
- 1977-05-18 FR FR7715331A patent/FR2352039A1/fr active Granted
- 1977-05-18 BR BR7703196A patent/BR7703196A/pt unknown
- 1977-05-18 JP JP5651277A patent/JPS52140540A/ja active Pending
- 1977-05-18 BE BE177728A patent/BE854819A/xx unknown
- 1977-05-18 CH CH620777A patent/CH618726A5/de not_active IP Right Cessation
- 1977-05-18 GB GB20916/77A patent/GB1543291A/en not_active Expired
- 1977-05-18 FR FR7715332A patent/FR2352040A1/fr active Granted
- 1977-05-18 CH CH620677A patent/CH618725A5/de not_active IP Right Cessation
- 1977-05-18 IT IT23736/77A patent/IT1143663B/it active
- 1977-05-18 JP JP5651177A patent/JPS52140539A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IN146336B (en, 2012) | 1979-05-05 |
| JPS52140540A (en) | 1977-11-24 |
| DE2622303A1 (de) | 1977-12-01 |
| GB1543453A (en) | 1979-04-04 |
| FR2352040A1 (fr) | 1977-12-16 |
| FR2352039B1 (en, 2012) | 1980-12-12 |
| NL7705270A (nl) | 1977-11-22 |
| US4144230A (en) | 1979-03-13 |
| IN146335B (en, 2012) | 1979-05-05 |
| JPS52140539A (en) | 1977-11-24 |
| BE854819A (fr) | 1977-11-18 |
| FR2352040B1 (en, 2012) | 1980-12-12 |
| BR7703196A (pt) | 1978-11-21 |
| CH618726A5 (en, 2012) | 1980-08-15 |
| GB1543291A (en) | 1979-04-04 |
| BR7703199A (pt) | 1978-05-23 |
| US4144231A (en) | 1979-03-13 |
| IT1143663B (it) | 1986-10-22 |
| FR2352039A1 (fr) | 1977-12-16 |
| BE854820A (fr) | 1977-11-18 |
| NL7705269A (nl) | 1977-11-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |