CH618726A5 - - Google Patents
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- Publication number
- CH618726A5 CH618726A5 CH620777A CH620777A CH618726A5 CH 618726 A5 CH618726 A5 CH 618726A5 CH 620777 A CH620777 A CH 620777A CH 620777 A CH620777 A CH 620777A CH 618726 A5 CH618726 A5 CH 618726A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- hydroxynaphthalene
- amino
- sulfonic acid
- methyl
- Prior art date
Links
- 238000005859 coupling reaction Methods 0.000 claims description 231
- 230000008878 coupling Effects 0.000 claims description 229
- 238000010168 coupling process Methods 0.000 claims description 229
- 239000000975 dye Substances 0.000 claims description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- 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 21
- 239000000203 mixture Substances 0.000 claims description 21
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- BERPCVULMUPOER-UHFFFAOYSA-N Quinolinediol Chemical class C1=CC=C2NC(=O)C(O)=CC2=C1 BERPCVULMUPOER-UHFFFAOYSA-N 0.000 claims description 3
- 125000005239 aroylamino 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
- 150000003839 salts Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical class C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 description 70
- -1 acyl radical Chemical class 0.000 description 61
- PUMBCOJMQGIIEW-UHFFFAOYSA-N 3-(3-oxobutanoylamino)benzenesulfonic acid Chemical compound CC(=O)CC(=O)NC1=CC=CC(S(O)(=O)=O)=C1 PUMBCOJMQGIIEW-UHFFFAOYSA-N 0.000 description 55
- 229920000742 Cotton Polymers 0.000 description 52
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 45
- AHGAATVNMMXRGX-UHFFFAOYSA-N 2,5-dichloro-4-(5-oxo-1H-pyrazol-2-yl)benzenesulfonic acid Chemical compound ClC1=C(C=C(C(=C1)S(=O)(=O)O)Cl)N1NC(C=C1)=O AHGAATVNMMXRGX-UHFFFAOYSA-N 0.000 description 42
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 39
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 31
- URNUWVIPNDXJGL-UHFFFAOYSA-N 2-chloro-1-(6-methoxy-2,2,4-trimethyl-3,4-dihydroquinolin-1-yl)ethanone Chemical compound ClCC(=O)N1C(C)(C)CC(C)C2=CC(OC)=CC=C21 URNUWVIPNDXJGL-UHFFFAOYSA-N 0.000 description 29
- HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 description 28
- RTTKVNNZRGYCTK-UHFFFAOYSA-N CC=1C=C(O)N(C)C(=O)C=1C#N Chemical compound CC=1C=C(O)N(C)C(=O)C=1C#N RTTKVNNZRGYCTK-UHFFFAOYSA-N 0.000 description 28
- 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 26
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 23
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 23
- 229960004889 salicylic acid Drugs 0.000 description 23
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 22
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 21
- JRQMRDBHOIOIIL-UHFFFAOYSA-N 3-methyl-1,5-dihydropyrazol-4-one Chemical compound CC1=NNCC1=O JRQMRDBHOIOIIL-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229950011260 betanaphthol Drugs 0.000 description 18
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 13
- 238000004043 dyeing Methods 0.000 description 13
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 12
- MVOJSQFOYYUOIK-UHFFFAOYSA-N C(CC(=O)C)(=O)NC1=C(C=CC(=C1)S(=O)(=O)O)S(=O)(=O)O Chemical compound C(CC(=O)C)(=O)NC1=C(C=CC(=C1)S(=O)(=O)O)S(=O)(=O)O MVOJSQFOYYUOIK-UHFFFAOYSA-N 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 11
- 229940018563 3-aminophenol Drugs 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 9
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 9
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 8
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- PBPYJPBSQRQFET-UHFFFAOYSA-N 4-(5-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1N1NC(=O)C=C1 PBPYJPBSQRQFET-UHFFFAOYSA-N 0.000 description 7
- JJHVYGVVMBYCMQ-UHFFFAOYSA-N 6-hydroxy-4-methyl-1h-pyridin-2-one Chemical compound CC=1C=C(O)NC(=O)C=1 JJHVYGVVMBYCMQ-UHFFFAOYSA-N 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 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 6
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 6
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 6
- ZFKLHLPATMPOHT-UHFFFAOYSA-N 2-(3-oxobutanoylamino)benzenesulfonic acid Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1S(O)(=O)=O ZFKLHLPATMPOHT-UHFFFAOYSA-N 0.000 description 6
- TUYGZKGBNXXXKR-UHFFFAOYSA-N 2-[(8-hydroxy-6-sulfonaphthalen-2-yl)amino]acetic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NCC(=O)O)=CC=C21 TUYGZKGBNXXXKR-UHFFFAOYSA-N 0.000 description 6
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 6
- 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 5
- GYFZMCLUPHXUDV-UHFFFAOYSA-N 2-ethoxy-5-methylaniline Chemical compound CCOC1=CC=C(C)C=C1N GYFZMCLUPHXUDV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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
- LRPIENHBUQIGPP-UHFFFAOYSA-N 6-(dimethylamino)-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N(C)C)=CC=C21 LRPIENHBUQIGPP-UHFFFAOYSA-N 0.000 description 5
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- SDQUDWYMWXUWPV-UHFFFAOYSA-N 2-(3-hydroxyanilino)acetic acid Chemical compound OC(=O)CNC1=CC=CC(O)=C1 SDQUDWYMWXUWPV-UHFFFAOYSA-N 0.000 description 4
- SIVZFLKJXSKCGT-UHFFFAOYSA-N 2-(naphthalen-1-ylamino)acetic acid Chemical compound C1=CC=C2C(NCC(=O)O)=CC=CC2=C1 SIVZFLKJXSKCGT-UHFFFAOYSA-N 0.000 description 4
- GRLSWESXIFWOBF-UHFFFAOYSA-N 4-(3-oxobutanoylamino)benzenesulfonic acid Chemical compound CC(=O)CC(=O)NC1=CC=C(S(O)(=O)=O)C=C1 GRLSWESXIFWOBF-UHFFFAOYSA-N 0.000 description 4
- HUYJTJXLNBOVFO-UHFFFAOYSA-N 7-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(O)=CC=C21 HUYJTJXLNBOVFO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 244000154870 Viola adunca Species 0.000 description 4
- 235000005811 Viola adunca Nutrition 0.000 description 4
- 235000013487 Viola odorata Nutrition 0.000 description 4
- 235000002254 Viola papilionacea Nutrition 0.000 description 4
- 244000172533 Viola sororia Species 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000003931 anilides Chemical class 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 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
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- 229960003742 phenol Drugs 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-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 3
- CAGFRYTXYKVXFU-UHFFFAOYSA-N 2-[(5-hydroxy-7-sulfonaphthalen-2-yl)amino]acetic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NCC(=O)O)=CC=C21 CAGFRYTXYKVXFU-UHFFFAOYSA-N 0.000 description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 3
- MKMDCEXRIPLNGJ-UHFFFAOYSA-N 2-phenyl-1h-pyrazol-5-one Chemical compound N1=C(O)C=CN1C1=CC=CC=C1 MKMDCEXRIPLNGJ-UHFFFAOYSA-N 0.000 description 3
- DACUJXBUANTBKE-UHFFFAOYSA-N 4-acetamido-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 DACUJXBUANTBKE-UHFFFAOYSA-N 0.000 description 3
- SEHCLGZKORRUKN-UHFFFAOYSA-N 4-hydroxy-6-(methylamino)naphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(NC)=CC=C21 SEHCLGZKORRUKN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QEAYLNJEDDOYNQ-UHFFFAOYSA-N 6-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=C1NC1=CC=CC=C1 QEAYLNJEDDOYNQ-UHFFFAOYSA-N 0.000 description 3
- WJPHPOIVNDQZFI-UHFFFAOYSA-N 6-hydroxy-1,4-dimethylpyridin-2-one Chemical compound CC=1C=C(O)N(C)C(=O)C=1 WJPHPOIVNDQZFI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 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
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- WNRVXVWPXKDOEB-UHFFFAOYSA-N 4-methylpyrazol-3-one Chemical compound CC1=CN=NC1=O WNRVXVWPXKDOEB-UHFFFAOYSA-N 0.000 description 1
- DPIZKMGPXNXSGL-UHFFFAOYSA-N 4-nitro-1,3-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C(N)=C1 DPIZKMGPXNXSGL-UHFFFAOYSA-N 0.000 description 1
- XHNZJATUNDXBDM-UHFFFAOYSA-N 5-amino-4-hydroxy-6-(2-hydroxyethyl)naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=C(CCO)C=CC2=C1 XHNZJATUNDXBDM-UHFFFAOYSA-N 0.000 description 1
- APFZZTVFVGUYBE-UHFFFAOYSA-N 5-amino-4-hydroxy-6-phenylnaphthalene-2-sulfonic acid Chemical compound C1=CC2=CC(S(O)(=O)=O)=CC(O)=C2C(N)=C1C1=CC=CC=C1 APFZZTVFVGUYBE-UHFFFAOYSA-N 0.000 description 1
- CFZAOQASYGKUBO-UHFFFAOYSA-N 5-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=CC2=C1 CFZAOQASYGKUBO-UHFFFAOYSA-N 0.000 description 1
- GHCFYCCXEKHAHC-UHFFFAOYSA-N 5-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1S(O)(=O)=O GHCFYCCXEKHAHC-UHFFFAOYSA-N 0.000 description 1
- WODYVAQBKKLESH-UHFFFAOYSA-N 5-methyl-1,3-benzothiazol-6-amine Chemical compound C1=C(N)C(C)=CC2=C1SC=N2 WODYVAQBKKLESH-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-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
- PYILOHKMJBLDHQ-UHFFFAOYSA-N 7-(methylamino)naphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(NC)=CC=C21 PYILOHKMJBLDHQ-UHFFFAOYSA-N 0.000 description 1
- WSUYONLKFXZZRV-UHFFFAOYSA-N 7-aminonaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(N)=CC=C21 WSUYONLKFXZZRV-UHFFFAOYSA-N 0.000 description 1
- YGNDWDUEMICDLW-UHFFFAOYSA-N 7-anilino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C=1C=C2C(O)=CC(S(O)(=O)=O)=CC2=CC=1NC1=CC=CC=C1 YGNDWDUEMICDLW-UHFFFAOYSA-N 0.000 description 1
- KAYRYDRCKNHDLO-UHFFFAOYSA-N 7-chloro-3h-benzimidazol-5-amine Chemical compound NC1=CC(Cl)=C2NC=NC2=C1 KAYRYDRCKNHDLO-UHFFFAOYSA-N 0.000 description 1
- DOBIZWYVJFIYOV-UHFFFAOYSA-N 7-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(O)=CC=C21 DOBIZWYVJFIYOV-UHFFFAOYSA-N 0.000 description 1
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HTPGTZUQERNOFP-UHFFFAOYSA-N C(CC(=O)C)(=O)NC1=C(C=C(C=C1S(=O)(=O)O)C)C Chemical compound C(CC(=O)C)(=O)NC1=C(C=C(C=C1S(=O)(=O)O)C)C HTPGTZUQERNOFP-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
- HKBLZPVQZRUAAO-UHFFFAOYSA-N CN1C(=NC2=C1C=CC(=C2)N)C2=CC=C(C=C2)N.CN2C(=NC1=C2C=C(C=C1)N)C1=CC=C(C=C1)N Chemical compound CN1C(=NC2=C1C=CC(=C2)N)C2=CC=C(C=C2)N.CN2C(=NC1=C2C=C(C=C1)N)C1=CC=C(C=C1)N HKBLZPVQZRUAAO-UHFFFAOYSA-N 0.000 description 1
- PYUHATCEYABQQM-UHFFFAOYSA-N COC=1C=C(C=CC1)O.ClC=1C=C(C=CC1)O Chemical compound COC=1C=C(C=CC1)O.ClC=1C=C(C=CC1)O PYUHATCEYABQQM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- LEXWCSFQFKBYQY-UHFFFAOYSA-N NC1=CC(=C(C=C1)S(=O)(=O)O)N.NC1=CC(=CC=C1)NCCS(=O)(=O)O Chemical compound NC1=CC(=C(C=C1)S(=O)(=O)O)N.NC1=CC(=CC=C1)NCCS(=O)(=O)O LEXWCSFQFKBYQY-UHFFFAOYSA-N 0.000 description 1
- DUGUMMYMULPNCW-UHFFFAOYSA-N NC1=CC2=C(C=C(C=C2C=C1)S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=CC(=CC(=C2C=C1)S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=C(C=CC=C2C(=C1)S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=CC=C(C=C2C=C1S(=O)(=O)O)S(=O)(=O)O Chemical compound NC1=CC2=C(C=C(C=C2C=C1)S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=CC(=CC(=C2C=C1)S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=C(C=CC=C2C(=C1)S(=O)(=O)O)S(=O)(=O)O.NC1=CC2=CC=C(C=C2C=C1S(=O)(=O)O)S(=O)(=O)O DUGUMMYMULPNCW-UHFFFAOYSA-N 0.000 description 1
- OJZSZYJYEHHSBX-UHFFFAOYSA-N OC1=CC=CC2=CC=CC=C12.OC1=CC=CC2=CC(=CC=C12)O Chemical compound OC1=CC=CC2=CC=CC=C12.OC1=CC=CC2=CC(=CC=C12)O OJZSZYJYEHHSBX-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L acid green 5 Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- XFAIQVVTPAQNKL-UHFFFAOYSA-N benzene-1,3-diamine;4-methylbenzene-1,3-diamine Chemical compound NC1=CC=CC(N)=C1.CC1=CC=C(N)C=C1N XFAIQVVTPAQNKL-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- ZZNZFBULEPJXCW-UHFFFAOYSA-N chembl1213563 Chemical compound CC1=CC(O)=NC(O)=C1C(O)=O ZZNZFBULEPJXCW-UHFFFAOYSA-N 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 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 1
- RBQWGHBZCHFUQU-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(N)=C1 RBQWGHBZCHFUQU-UHFFFAOYSA-N 0.000 description 1
- VGDKCRMZIWPMPW-UHFFFAOYSA-N n-(3-aminophenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(N)=C1 VGDKCRMZIWPMPW-UHFFFAOYSA-N 0.000 description 1
- MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
- ODFRAIZRJMUPCP-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1C ODFRAIZRJMUPCP-UHFFFAOYSA-N 0.000 description 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
- MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-UHFFFAOYSA-N 0.000 description 1
- FKNGBLJXFDHNES-UHFFFAOYSA-N n-(5-hydroxynaphthalen-2-yl)acetamide Chemical compound OC1=CC=CC2=CC(NC(=O)C)=CC=C21 FKNGBLJXFDHNES-UHFFFAOYSA-N 0.000 description 1
- TVEJCFVSJDAOMZ-UHFFFAOYSA-N n-(8-hydroxynaphthalen-2-yl)acetamide Chemical compound C1=CC=C(O)C2=CC(NC(=O)C)=CC=C21 TVEJCFVSJDAOMZ-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JMRJWEJJUKUBEA-UHFFFAOYSA-N p-Chloroacetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1 JMRJWEJJUKUBEA-UHFFFAOYSA-N 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 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
- 239000000758 substrate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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 |
|---|---|
| CH618726A5 true CH618726A5 (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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH620677A CH618725A5 (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 |
|---|---|
| CH618725A5 (en, 2012) | 1980-08-15 |
| 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 |
| 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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