CH625541A5 - Process for preparing azo dyes - Google Patents
Process for preparing azo dyes Download PDFInfo
- Publication number
- CH625541A5 CH625541A5 CH119577A CH119577A CH625541A5 CH 625541 A5 CH625541 A5 CH 625541A5 CH 119577 A CH119577 A CH 119577A CH 119577 A CH119577 A CH 119577A CH 625541 A5 CH625541 A5 CH 625541A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- amino
- weight
- aniline
- coupling
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 71
- 238000005859 coupling reaction Methods 0.000 claims description 68
- 230000008878 coupling Effects 0.000 claims description 67
- 238000010168 coupling process Methods 0.000 claims description 67
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 43
- -1 phenalkoxy Chemical group 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000001989 diazonium salts Chemical class 0.000 claims description 13
- 239000002270 dispersing agent Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 235000010288 sodium nitrite Nutrition 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000005521 carbonamide group Chemical group 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 229940106681 chloroacetic acid Drugs 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical group 0.000 claims 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000004304 potassium nitrite Substances 0.000 claims 1
- 235000010289 potassium nitrite Nutrition 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
- 239000000975 dye Substances 0.000 description 25
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 3
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 3
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 3
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- ACCLIXSHFMDCLV-UHFFFAOYSA-N 3-[n-(2-phenylethyl)anilino]propanenitrile Chemical compound C=1C=CC=CC=1N(CCC#N)CCC1=CC=CC=C1 ACCLIXSHFMDCLV-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
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- MYVQLRNSRCNCJY-UHFFFAOYSA-N (2-amino-4,5-dimethylphenyl)-phenylmethanone Chemical compound C1=C(C)C(C)=CC(N)=C1C(=O)C1=CC=CC=C1 MYVQLRNSRCNCJY-UHFFFAOYSA-N 0.000 description 1
- LDSAJELEAILFKT-UHFFFAOYSA-N (2-aminophenyl)-(2,4-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC=C1C(=O)C1=CC=CC=C1N LDSAJELEAILFKT-UHFFFAOYSA-N 0.000 description 1
- FLORUWDSYNSEAH-UHFFFAOYSA-N (2-aminophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1N FLORUWDSYNSEAH-UHFFFAOYSA-N 0.000 description 1
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- HFZPYPRRAVDPBX-UHFFFAOYSA-N (3-aminophenyl)-(3,4-dimethoxyphenyl)methanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C1=CC=CC(N)=C1 HFZPYPRRAVDPBX-UHFFFAOYSA-N 0.000 description 1
- GHHYIYWROJLOLU-UHFFFAOYSA-N (3-aminophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC(N)=C1 GHHYIYWROJLOLU-UHFFFAOYSA-N 0.000 description 1
- FUADXEJBHCKVBN-UHFFFAOYSA-N (3-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FUADXEJBHCKVBN-UHFFFAOYSA-N 0.000 description 1
- MPVSFTZGKDYDIA-UHFFFAOYSA-N (4-aminophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1 MPVSFTZGKDYDIA-UHFFFAOYSA-N 0.000 description 1
- STUSEHMGXDHGKL-UHFFFAOYSA-N (4-aminophenyl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC=C(N)C=C1 STUSEHMGXDHGKL-UHFFFAOYSA-N 0.000 description 1
- IZSRTZLNLWGKMS-UHFFFAOYSA-N (4-aminophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(N)C=C1 IZSRTZLNLWGKMS-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
- MCKVZMYDTPNJFK-UHFFFAOYSA-N 1-[4-[(4-amino-2,5-dimethylphenyl)diazenyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N=NC1=CC(C)=C(N)C=C1C MCKVZMYDTPNJFK-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- JBXZCPXEYAEMJS-UHFFFAOYSA-N 2,5-dichloro-4-nitroaniline Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl JBXZCPXEYAEMJS-UHFFFAOYSA-N 0.000 description 1
- KBJGBAOGDZOYIZ-UHFFFAOYSA-N 2,5-dimethoxy-4-[(4-nitrophenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC(=CC=2)[N+]([O-])=O)=C1OC KBJGBAOGDZOYIZ-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- CSFKBRKMUJANAJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)sulfonylaniline Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=CC=CC=C1N CSFKBRKMUJANAJ-UHFFFAOYSA-N 0.000 description 1
- RVDMVLINQHMAGO-UHFFFAOYSA-N 2-(benzenesulfonyl)-5-chloroaniline Chemical compound NC1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC=C1 RVDMVLINQHMAGO-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 1
- BUHDOMOJOMCPRZ-UHFFFAOYSA-N 2-[(2-chloro-4-nitrophenyl)diazenyl]-5-methoxy-4-methylaniline Chemical compound C1=C(C)C(OC)=CC(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl BUHDOMOJOMCPRZ-UHFFFAOYSA-N 0.000 description 1
- BPUKIHNFTCELIR-UHFFFAOYSA-N 2-[(4-amino-2,5-dimethylphenyl)diazenyl]-5-nitrobenzonitrile Chemical compound C1=C(N)C(C)=CC(N=NC=2C(=CC(=CC=2)[N+]([O-])=O)C#N)=C1C BPUKIHNFTCELIR-UHFFFAOYSA-N 0.000 description 1
- QYNPSKMCWDQPCD-UHFFFAOYSA-N 2-[(4-amino-5-methoxy-2-methylphenyl)diazenyl]-5-nitrobenzonitrile Chemical compound C1=C(N)C(OC)=CC(N=NC=2C(=CC(=CC=2)[N+]([O-])=O)C#N)=C1C QYNPSKMCWDQPCD-UHFFFAOYSA-N 0.000 description 1
- VMNDRLYLEVCGAG-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-3-methylanilino]ethanol Chemical compound CC1=CC=CC(N(CCO)CCO)=C1 VMNDRLYLEVCGAG-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- RIYSFSQPHCAGLS-UHFFFAOYSA-N 2-amino-3,5-dinitrobenzonitrile Chemical compound NC1=C(C#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O RIYSFSQPHCAGLS-UHFFFAOYSA-N 0.000 description 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
- KWMDHCLJYMVBNS-UHFFFAOYSA-N 2-bromo-4,6-dinitroaniline Chemical compound NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KWMDHCLJYMVBNS-UHFFFAOYSA-N 0.000 description 1
- IWOLQYSFQMZXIZ-UHFFFAOYSA-N 2-butan-2-yloxy-4-[(2-chloro-4-nitrophenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC(C)CC)=CC(N=NC=2C(=CC(=CC=2)[N+]([O-])=O)Cl)=C1 IWOLQYSFQMZXIZ-UHFFFAOYSA-N 0.000 description 1
- IIKVAWLYHHZRGV-UHFFFAOYSA-N 2-carbazol-9-ylethanol Chemical compound C1=CC=C2N(CCO)C3=CC=CC=C3C2=C1 IIKVAWLYHHZRGV-UHFFFAOYSA-N 0.000 description 1
- QOLLIIWSFZEEFD-UHFFFAOYSA-N 2-carbazol-9-ylethyl acetate Chemical compound C1=CC=C2N(CCOC(=O)C)C3=CC=CC=C3C2=C1 QOLLIIWSFZEEFD-UHFFFAOYSA-N 0.000 description 1
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- YJPKSWNLIDWGNJ-UHFFFAOYSA-N 4-[[4-(trifluoromethyl)phenyl]diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(C(F)(F)F)C=C1 YJPKSWNLIDWGNJ-UHFFFAOYSA-N 0.000 description 1
- QDNOBTKJPANVQD-UHFFFAOYSA-N 4-amino-2-chloro-5-nitrobenzonitrile Chemical compound NC1=CC(Cl)=C(C#N)C=C1[N+]([O-])=O QDNOBTKJPANVQD-UHFFFAOYSA-N 0.000 description 1
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- QEPGWLBMAAEBCP-UHFFFAOYSA-N 4-amino-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(N)C=C1 QEPGWLBMAAEBCP-UHFFFAOYSA-N 0.000 description 1
- BABGMPQXLCJMSK-UHFFFAOYSA-N 4-amino-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(N)C=C1 BABGMPQXLCJMSK-UHFFFAOYSA-N 0.000 description 1
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- SQFONLULGFXJAA-UHFFFAOYSA-N 9-butylcarbazole Chemical compound C1=CC=C2N(CCCC)C3=CC=CC=C3C2=C1 SQFONLULGFXJAA-UHFFFAOYSA-N 0.000 description 1
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- YUQFIRCVYLJADW-UHFFFAOYSA-N BrC1=C(N)C(=CC(=C1)Br)Br.ClC1=C(N)C(=CC(=C1)Cl)Cl.ClC1=C(N)C=C(C=C1)Cl Chemical compound BrC1=C(N)C(=CC(=C1)Br)Br.ClC1=C(N)C(=CC(=C1)Cl)Cl.ClC1=C(N)C=C(C=C1)Cl YUQFIRCVYLJADW-UHFFFAOYSA-N 0.000 description 1
- NYFUUNPFTQHJIU-UHFFFAOYSA-N C(C)N(C1=C(C=CC(=C1)NC(C)=O)OC)CC1=CC=CC=C1.CN(C1=CC(=CC=C1)Cl)C Chemical compound C(C)N(C1=C(C=CC(=C1)NC(C)=O)OC)CC1=CC=CC=C1.CN(C1=CC(=CC=C1)Cl)C NYFUUNPFTQHJIU-UHFFFAOYSA-N 0.000 description 1
- JNCJVOVZKUXHDU-UHFFFAOYSA-N C(C)OC1=C(N)C=CC(=C1)[N+](=O)[O-].COC1=CC(=C(N)C=C1)[N+](=O)[O-].COC1=C(N)C=CC(=C1)[N+](=O)[O-].BrC1=C(N)C=CC(=C1)[N+](=O)[O-] Chemical compound C(C)OC1=C(N)C=CC(=C1)[N+](=O)[O-].COC1=CC(=C(N)C=C1)[N+](=O)[O-].COC1=C(N)C=CC(=C1)[N+](=O)[O-].BrC1=C(N)C=CC(=C1)[N+](=O)[O-] JNCJVOVZKUXHDU-UHFFFAOYSA-N 0.000 description 1
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 1
- BTWJGUSSFSXZEX-UHFFFAOYSA-N NC1=C(C=C(C=C1)N=NC1=CC=C(C=C1)[N+](=O)[O-])Cl.NC1=C(C=C(C=C1)N=NC1=CC(=CC=C1)[N+](=O)[O-])Cl Chemical compound NC1=C(C=C(C=C1)N=NC1=CC=C(C=C1)[N+](=O)[O-])Cl.NC1=C(C=C(C=C1)N=NC1=CC(=CC=C1)[N+](=O)[O-])Cl BTWJGUSSFSXZEX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 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
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- WXYUSEKPTVLYDI-UHFFFAOYSA-N ethyl 4-[(4-aminophenyl)diazenyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=NC1=CC=C(N)C=C1 WXYUSEKPTVLYDI-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000012535 impurity Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- FODZNORQIATQIP-UHFFFAOYSA-N methyl 2-amino-3,5-dichlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC(Cl)=C1N FODZNORQIATQIP-UHFFFAOYSA-N 0.000 description 1
- LOCJPOYKBUUVKU-UHFFFAOYSA-N methyl 3-amino-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N)=C1 LOCJPOYKBUUVKU-UHFFFAOYSA-N 0.000 description 1
- AIUWAOALZYWQBX-UHFFFAOYSA-N methyl 4-amino-3-bromobenzoate Chemical compound COC(=O)C1=CC=C(N)C(Br)=C1 AIUWAOALZYWQBX-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- AFABFCARSKKBAV-UHFFFAOYSA-N n-[3-(dibenzylamino)-4-methoxyphenyl]acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 AFABFCARSKKBAV-UHFFFAOYSA-N 0.000 description 1
- BTJCIVXKBILNPY-UHFFFAOYSA-N n-[3-(diethylamino)-4-methoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC(NC(C)=O)=CC=C1OC BTJCIVXKBILNPY-UHFFFAOYSA-N 0.000 description 1
- VJRJZSNBEQJSRB-UHFFFAOYSA-N n-[5-amino-2-[(2-cyano-4-nitrophenyl)diazenyl]-4-methoxyphenyl]acetamide Chemical compound C1=C(N)C(OC)=CC(N=NC=2C(=CC(=CC=2)[N+]([O-])=O)C#N)=C1NC(C)=O VJRJZSNBEQJSRB-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- RURHKMFOIJYFIP-UHFFFAOYSA-N phenyl 3-carbazol-9-ylpropanoate Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CCC(=O)OC1=CC=CC=C1 RURHKMFOIJYFIP-UHFFFAOYSA-N 0.000 description 1
- GAHFQFKNJAXQIP-UHFFFAOYSA-N phenyl 4-carbazol-9-ylbenzoate Chemical compound C=1C=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=CC=1C(=O)OC1=CC=CC=C1 GAHFQFKNJAXQIP-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 238000010626 work up procedure 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3608—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom
-
- 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
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/002—Special methods of performing the coupling reaction characterised by the coupling medium containing a solvent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2603836A DE2603836C3 (de) | 1976-02-02 | 1976-02-02 | Verfahren zur Herstellung von Azofarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625541A5 true CH625541A5 (en) | 1981-09-30 |
Family
ID=5968818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH119577A CH625541A5 (en) | 1976-02-02 | 1977-02-01 | Process for preparing azo dyes |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2834054A1 (de) * | 1978-08-03 | 1980-02-21 | Cassella Ag | Wasserunloesliche disazofarbstoffe, ihre herstellung und verwendung |
| EP0028464B1 (en) * | 1979-10-26 | 1983-05-25 | Imperial Chemical Industries Plc | Azo dyestuff preparation by phase transfer catalysed coupling in a two-phase medium |
| DE3710176A1 (de) * | 1987-03-27 | 1988-10-13 | Hoechst Ag | Verfahren zur herstellung des lithiumsalzes eines faserreaktiven azofarbstoffes |
| PL169333B1 (pl) * | 1992-05-26 | 1996-07-31 | Inst Chemii Przemyslowej Im Pr | Sposób wytwarzania nowych reaktywnych barwników karbazolowych PL |
| CN103497533A (zh) * | 2013-09-10 | 2014-01-08 | 江苏亚邦染料股份有限公司 | 一类杂环偶氮型分散染料及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE471540A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1946-03-01 | |||
| DE1927453U (de) | 1965-07-30 | 1965-11-18 | Fritz Zeller | Abferkelbucht. |
| FR1537367A (fr) * | 1966-09-22 | 1968-08-23 | Ciba Geigy | Procédé de fabrication de colorants azoïques pigmentaires |
| BE759438A (fr) | 1969-11-27 | 1971-05-26 | Geigy Ag J R | Procede de preparation de composes azoiques |
| US3793305A (en) | 1970-09-14 | 1974-02-19 | Du Pont | One-step process of preparing azo dyes by simultaneous diazotization |
| AR206142A1 (es) | 1974-03-08 | 1976-06-30 | Ciba Geigy Ag | Procedimiento para la obtencion de compuestos azoicos |
-
1976
- 1976-02-02 DE DE2603836A patent/DE2603836C3/de not_active Expired
-
1977
- 1977-01-26 NL NL7700788A patent/NL7700788A/xx not_active Application Discontinuation
- 1977-01-31 JP JP886777A patent/JPS5294324A/ja active Pending
- 1977-01-31 IT IT19816/77A patent/IT1113508B/it active
- 1977-01-31 FR FR7702573A patent/FR2339653A1/fr active Granted
- 1977-02-01 GB GB4023/77A patent/GB1535894A/en not_active Expired
- 1977-02-01 CH CH119577A patent/CH625541A5/de not_active IP Right Cessation
- 1977-02-01 BE BE174572A patent/BE850983A/xx unknown
- 1977-02-01 CA CA270,828A patent/CA1095898A/en not_active Expired
- 1977-02-01 IN IN145/CAL/77A patent/IN144273B/en unknown
- 1977-02-01 BR BR7700625A patent/BR7700625A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2339653A1 (fr) | 1977-08-26 |
| NL7700788A (nl) | 1977-08-04 |
| DE2603836B2 (de) | 1980-01-03 |
| BR7700625A (pt) | 1977-10-04 |
| CA1095898A (en) | 1981-02-17 |
| IT1113508B (it) | 1986-01-20 |
| BE850983A (fr) | 1977-08-01 |
| DE2603836A1 (de) | 1977-08-04 |
| DE2603836C3 (de) | 1980-09-04 |
| GB1535894A (en) | 1978-12-13 |
| IN144273B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-22 |
| FR2339653B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-24 |
| JPS5294324A (en) | 1977-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |