DE2347849A1 - Neue polyazofarbstoffe und verfahren zu ihrer herstellung - Google Patents
Neue polyazofarbstoffe und verfahren zu ihrer herstellungInfo
- Publication number
- DE2347849A1 DE2347849A1 DE19732347849 DE2347849A DE2347849A1 DE 2347849 A1 DE2347849 A1 DE 2347849A1 DE 19732347849 DE19732347849 DE 19732347849 DE 2347849 A DE2347849 A DE 2347849A DE 2347849 A1 DE2347849 A1 DE 2347849A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- above meaning
- stands
- aromatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 POLYAZO Polymers 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000000975 dye Substances 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 150000004982 aromatic amines Chemical class 0.000 claims description 13
- 150000004984 aromatic diamines Chemical class 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001491 aromatic compounds Chemical class 0.000 claims description 10
- 238000004043 dyeing Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000003277 amino 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 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- YGGXZTQSGNFKPJ-UHFFFAOYSA-N methyl 2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC=CC2=C1 YGGXZTQSGNFKPJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 101000720704 Homo sapiens Neuronal migration protein doublecortin Proteins 0.000 claims 1
- 102100025929 Neuronal migration protein doublecortin Human genes 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000002657 fibrous material Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 11
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 11
- 229940018564 m-phenylenediamine Drugs 0.000 description 10
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 8
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 8
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000711 cancerogenic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- YOKGFEBGKOKPBX-UHFFFAOYSA-N 4-[3-(4-aminophenyl)-1h-1,2,4-triazol-5-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NNC(C=2C=CC(N)=CC=2)=N1 YOKGFEBGKOKPBX-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- IEHABTGUFDPZLD-UHFFFAOYSA-N 4-[5-(4-aminophenyl)furan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(C=2C=CC(N)=CC=2)O1 IEHABTGUFDPZLD-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- CKLPECFHCLIYKN-UHFFFAOYSA-N n'-phenylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)NNC1=CC=CC=C1 CKLPECFHCLIYKN-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- UERKTBSAPLOJRQ-UHFFFAOYSA-N 1-amino-1-phenylurea Chemical compound NC(=O)N(N)C1=CC=CC=C1 UERKTBSAPLOJRQ-UHFFFAOYSA-N 0.000 description 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-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
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-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
- JYJPXACGURQSCB-UHFFFAOYSA-N 2-(2-methylphenoxy)aniline Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1N JYJPXACGURQSCB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- UCGZNHXYVJOCMV-UHFFFAOYSA-N 2-amino-2-(3-aminophenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC=CC(N)=C1 UCGZNHXYVJOCMV-UHFFFAOYSA-N 0.000 description 1
- BPXLXNLDJGWLDW-UHFFFAOYSA-N 2-amino-5-benzamidobenzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1NC(=O)C1=CC=CC=C1 BPXLXNLDJGWLDW-UHFFFAOYSA-N 0.000 description 1
- KTFUNVBAGAPLLC-UHFFFAOYSA-N 2-amino-5-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(N)C(S(O)(=O)=O)=C1 KTFUNVBAGAPLLC-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- KEZQMIXMRWJLFE-UHFFFAOYSA-N 2-methoxy-n'-phenylacetohydrazide Chemical compound COCC(=O)NNC1=CC=CC=C1 KEZQMIXMRWJLFE-UHFFFAOYSA-N 0.000 description 1
- LEQAQBFYCMENLP-UHFFFAOYSA-N 2-methoxy-n-phenylacetamide Chemical compound COCC(=O)NC1=CC=CC=C1 LEQAQBFYCMENLP-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NMFFUUFPJJOWHK-UHFFFAOYSA-N 2-phenoxyaniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1 NMFFUUFPJJOWHK-UHFFFAOYSA-N 0.000 description 1
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- XCNVGZLOCLSXHM-UHFFFAOYSA-N 3-[2-(3-aminophenyl)-1h-imidazol-5-yl]aniline Chemical compound NC1=CC=CC(C=2NC(=NC=2)C=2C=C(N)C=CC=2)=C1 XCNVGZLOCLSXHM-UHFFFAOYSA-N 0.000 description 1
- DGZCDSVVGISXSP-UHFFFAOYSA-N 3-[3-(3-aminophenyl)-1h-1,2,4-triazol-5-yl]aniline Chemical compound NC1=CC=CC(C=2N=C(NN=2)C=2C=C(N)C=CC=2)=C1 DGZCDSVVGISXSP-UHFFFAOYSA-N 0.000 description 1
- HJLLHYNMAUWCNS-UHFFFAOYSA-N 3-[5-(3-aminophenyl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=CC(C=2OC(=NN=2)C=2C=C(N)C=CC=2)=C1 HJLLHYNMAUWCNS-UHFFFAOYSA-N 0.000 description 1
- VBAKVBYIWHDUFP-UHFFFAOYSA-N 3-[5-(3-aminophenyl)-1,3,4-thiadiazol-2-yl]aniline Chemical compound NC1=CC=CC(C=2SC(=NN=2)C=2C=C(N)C=CC=2)=C1 VBAKVBYIWHDUFP-UHFFFAOYSA-N 0.000 description 1
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- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- ZOOPTFMVDWNNJH-UHFFFAOYSA-N aniline;4-nitroaniline Chemical compound NC1=CC=CC=C1.NC1=CC=C([N+]([O-])=O)C=C1 ZOOPTFMVDWNNJH-UHFFFAOYSA-N 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical compound CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 description 1
- GVUHTLABICJQTO-UHFFFAOYSA-N n-(1-hydroxynaphthalen-2-yl)acetamide Chemical compound C1=CC=CC2=C(O)C(NC(=O)C)=CC=C21 GVUHTLABICJQTO-UHFFFAOYSA-N 0.000 description 1
- VFTLSDNNKYIHNS-UHFFFAOYSA-N n-(1-hydroxynaphthalen-2-yl)benzamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1NC(=O)C1=CC=CC=C1 VFTLSDNNKYIHNS-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
- ZKMYHZKZDMIROQ-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)benzamide Chemical compound C1=C(N)C(C)=CC=C1NC(=O)C1=CC=CC=C1 ZKMYHZKZDMIROQ-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
- QXWUFIZOBXUMSM-UHFFFAOYSA-N n-(4-amino-3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C(C)=C1 QXWUFIZOBXUMSM-UHFFFAOYSA-N 0.000 description 1
- OOHBXBWEUPLRKO-UHFFFAOYSA-N n-(4-amino-3-methylphenyl)benzamide Chemical compound C1=C(N)C(C)=CC(NC(=O)C=2C=CC=CC=2)=C1 OOHBXBWEUPLRKO-UHFFFAOYSA-N 0.000 description 1
- ILGZVYUJXCQAKC-UHFFFAOYSA-N n-(4-amino-3-methylphenyl)formamide Chemical compound CC1=CC(NC=O)=CC=C1N ILGZVYUJXCQAKC-UHFFFAOYSA-N 0.000 description 1
- TZXNQOKMJUEVBI-UHFFFAOYSA-N n-(5-amino-2-methylphenyl)formamide Chemical compound CC1=CC=C(N)C=C1NC=O TZXNQOKMJUEVBI-UHFFFAOYSA-N 0.000 description 1
- AAFUAKIIYDTUJU-UHFFFAOYSA-N n-chloro-n-methoxyaniline Chemical compound CON(Cl)C1=CC=CC=C1 AAFUAKIIYDTUJU-UHFFFAOYSA-N 0.000 description 1
- JBCRGRUAARPEFD-UHFFFAOYSA-N n-chloro-n-methylaniline Chemical compound CN(Cl)C1=CC=CC=C1 JBCRGRUAARPEFD-UHFFFAOYSA-N 0.000 description 1
- LHHIALSOMNPUOW-UHFFFAOYSA-N n-chloro-n-phenylnitramide Chemical compound [O-][N+](=O)N(Cl)C1=CC=CC=C1 LHHIALSOMNPUOW-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- TXTHKGMZDDTZFD-UHFFFAOYSA-N n-cyclohexylaniline Chemical compound C1CCCCC1NC1=CC=CC=C1 TXTHKGMZDDTZFD-UHFFFAOYSA-N 0.000 description 1
- WMTJSRRNAJDUNE-UHFFFAOYSA-N n-methoxy-n-methylaniline Chemical compound CON(C)C1=CC=CC=C1 WMTJSRRNAJDUNE-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- ABRWESLGGMHKEA-UHFFFAOYSA-N n-tert-butylaniline Chemical compound CC(C)(C)NC1=CC=CC=C1 ABRWESLGGMHKEA-UHFFFAOYSA-N 0.000 description 1
- SKMPRPUCTZWWAQ-UHFFFAOYSA-N naphthalen-1-ol;naphthalen-2-ol Chemical compound C1=CC=CC2=CC(O)=CC=C21.C1=CC=C2C(O)=CC=CC2=C1 SKMPRPUCTZWWAQ-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
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- CKQORTPXQDLZGH-UHFFFAOYSA-N tetrazine-5,6-diamine Chemical compound NC1=NN=NN=C1N CKQORTPXQDLZGH-UHFFFAOYSA-N 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 238000005406 washing Methods 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47095707A JPS5227650B2 (enrdf_load_html_response) | 1972-09-22 | 1972-09-22 | |
| JP2979173A JPS5222364B2 (enrdf_load_html_response) | 1973-03-14 | 1973-03-14 | |
| JP48029835A JPS5230007B2 (enrdf_load_html_response) | 1973-03-14 | 1973-03-14 | |
| JP2979073A JPS5143110B2 (enrdf_load_html_response) | 1973-03-14 | 1973-03-14 | |
| JP4694573A JPS5228129B2 (enrdf_load_html_response) | 1973-04-24 | 1973-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2347849A1 true DE2347849A1 (de) | 1974-03-28 |
Family
ID=27521172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732347849 Pending DE2347849A1 (de) | 1972-09-22 | 1973-09-22 | Neue polyazofarbstoffe und verfahren zu ihrer herstellung |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH1353173A4 (enrdf_load_html_response) |
| DE (1) | DE2347849A1 (enrdf_load_html_response) |
| FR (1) | FR2200331B1 (enrdf_load_html_response) |
| GB (1) | GB1439238A (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424501A1 (de) * | 1974-05-20 | 1975-12-11 | Cassella Farbwerke Mainkur Ag | Loesliche trisazofarbstoffe, ihre herstellung und verwendung |
| US4784668A (en) * | 1986-05-30 | 1988-11-15 | Basf Aktiengesellschaft | Novel heterocycle-containing trisazo dyes |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2553261C2 (de) * | 1975-11-27 | 1983-01-27 | Cassella Ag, 6000 Frankfurt | Wasserlösliche Trisazofarbstoffe, ihre Herstellung und Verwendung |
| JP2986605B2 (ja) * | 1992-02-12 | 1999-12-06 | オリヱント化学工業株式会社 | 新規トリスアゾ染料およびこれらを含有する染料組成物 |
-
1973
- 1973-09-20 GB GB4415473A patent/GB1439238A/en not_active Expired
- 1973-09-20 CH CH1353173D patent/CH1353173A4/xx unknown
- 1973-09-20 CH CH1353173A patent/CH569133B5/xx not_active IP Right Cessation
- 1973-09-22 DE DE19732347849 patent/DE2347849A1/de active Pending
- 1973-09-24 FR FR7334097A patent/FR2200331B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424501A1 (de) * | 1974-05-20 | 1975-12-11 | Cassella Farbwerke Mainkur Ag | Loesliche trisazofarbstoffe, ihre herstellung und verwendung |
| US4784668A (en) * | 1986-05-30 | 1988-11-15 | Basf Aktiengesellschaft | Novel heterocycle-containing trisazo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| CH1353173A4 (enrdf_load_html_response) | 1975-05-30 |
| CH569133B5 (enrdf_load_html_response) | 1975-11-14 |
| FR2200331B1 (enrdf_load_html_response) | 1977-05-27 |
| FR2200331A1 (enrdf_load_html_response) | 1974-04-19 |
| GB1439238A (en) | 1976-06-16 |
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