DE2304218C2 - Disperse Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen Textilmaterialien - Google Patents
Disperse Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen TextilmaterialienInfo
- Publication number
- DE2304218C2 DE2304218C2 DE19732304218 DE2304218A DE2304218C2 DE 2304218 C2 DE2304218 C2 DE 2304218C2 DE 19732304218 DE19732304218 DE 19732304218 DE 2304218 A DE2304218 A DE 2304218A DE 2304218 C2 DE2304218 C2 DE 2304218C2
- Authority
- DE
- Germany
- Prior art keywords
- carbonyl
- lower alkyl
- amino
- ethyl
- alkyl
- 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.)
- Expired
Links
- 239000000463 material Substances 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 11
- 238000004043 dyeing Methods 0.000 title claims description 9
- 229920002994 synthetic fiber Polymers 0.000 title claims description 8
- 239000004758 synthetic textile Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000987 azo dye Substances 0.000 title description 4
- -1 nitro, cyano, phenyl Chemical group 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 48
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
- 239000000975 dye Substances 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 238000005859 coupling reaction Methods 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 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
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 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 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DZRZHFOFVWAKGT-UHFFFAOYSA-N 3,5-dinitrothiophen-2-amine Chemical compound NC=1SC([N+]([O-])=O)=CC=1[N+]([O-])=O DZRZHFOFVWAKGT-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 3
- NTICRYSYQVALQQ-UHFFFAOYSA-N 5-bromo-4-nitrothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C(Br)S1 NTICRYSYQVALQQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- IDAQSADEMXDTKN-UHFFFAOYSA-L ethyl green Chemical compound [Cl-].[Br-].C1=CC([N+](C)(C)CC)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C1C=CC(=[N+](C)C)C=C1 IDAQSADEMXDTKN-UHFFFAOYSA-L 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YWCFEQPZXHQSSS-UHFFFAOYSA-N 2-acetamido-4-methylthiophene-3-carboxylic acid Chemical compound CC(=O)NC=1SC=C(C)C=1C(O)=O YWCFEQPZXHQSSS-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- UPLNWDVLIXWYFM-UHFFFAOYSA-N 2-bromo-3,4,5-trinitrothiophene Chemical compound [O-][N+](=O)C=1SC(Br)=C([N+]([O-])=O)C=1[N+]([O-])=O UPLNWDVLIXWYFM-UHFFFAOYSA-N 0.000 description 1
- FLJWVVUJGVNXMZ-UHFFFAOYSA-N 2-sulfanylacetaldehyde Chemical compound SCC=O FLJWVVUJGVNXMZ-UHFFFAOYSA-N 0.000 description 1
- FDYLWXZGLNXBQT-UHFFFAOYSA-N 3,4,5-trinitrothiophen-2-amine Chemical compound NC=1SC([N+]([O-])=O)=C([N+]([O-])=O)C=1[N+]([O-])=O FDYLWXZGLNXBQT-UHFFFAOYSA-N 0.000 description 1
- VVJZYYJUJFGNKU-UHFFFAOYSA-N 5-amino-4-nitrothiophene-2-carbonitrile Chemical compound NC=1SC(C#N)=CC=1[N+]([O-])=O VVJZYYJUJFGNKU-UHFFFAOYSA-N 0.000 description 1
- VDZHPIXTSQDZIN-UHFFFAOYSA-N 5-amino-4-nitrothiophene-2-carboxamide Chemical compound NC(=O)C1=CC([N+]([O-])=O)=C(N)S1 VDZHPIXTSQDZIN-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- JWFJVXWDXGXGDV-UHFFFAOYSA-N ethyl 5-amino-4-nitrothiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC([N+]([O-])=O)=C(N)S1 JWFJVXWDXGXGDV-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- RYHPGKJBLSYSCH-UHFFFAOYSA-N n-(5-formylthiophen-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(C=O)S1 RYHPGKJBLSYSCH-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur 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
- 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
-
- 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
- C09B29/06—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
-
- 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
-
- 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
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
-
- 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
- C09B29/3695—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing other heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB404672A GB1394365A (en) | 1972-01-28 | 1972-01-28 | Disperse azo dyestuffs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2304218A1 DE2304218A1 (de) | 1973-08-02 |
| DE2304218C2 true DE2304218C2 (de) | 1983-01-05 |
Family
ID=9769733
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732304218 Expired DE2304218C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen Textilmaterialien |
| DE19732304202 Expired DE2304202C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19732304203 Expired DE2304203C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien |
| DE19732304201 Expired DE2304201C2 (de) | 1972-01-28 | 1973-01-29 | 2-Aminothiophene |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732304202 Expired DE2304202C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19732304203 Expired DE2304203C2 (de) | 1972-01-28 | 1973-01-29 | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien |
| DE19732304201 Expired DE2304201C2 (de) | 1972-01-28 | 1973-01-29 | 2-Aminothiophene |
Country Status (11)
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079050A (en) * | 1972-01-28 | 1978-03-14 | Imperial Chemical Industries Limited | Disperse monoazo dyestuffs containing a thiophene residue |
| NL7309098A (enrdf_load_stackoverflow) * | 1972-07-04 | 1974-01-08 | ||
| CH554395A (de) * | 1972-07-11 | 1974-09-30 | Sandoz Ag | Verfahren zur herstellung in wasser schwer loeslicher azoverbindungen. |
| AR204517A1 (es) * | 1972-12-01 | 1976-02-12 | Sandoz Ag | Procedimiento para obtener compuestos de 5-ciano-2-amino-tiofenos |
| CH584257A5 (enrdf_load_stackoverflow) * | 1973-09-06 | 1977-01-31 | Sandoz Ag | |
| US4140683A (en) * | 1976-02-23 | 1979-02-20 | Eastman Kodak Company | Dyes from thienylazo compounds and cyclohexylaminoacylanilide couplers |
| GB1583377A (en) * | 1977-04-25 | 1981-01-28 | Ici Ltd | Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde |
| US4204991A (en) * | 1977-10-25 | 1980-05-27 | G. D. Searle & Co. | Sarcosine1 dehydroalanine8 angiotensin II derivatives |
| DE2759103C2 (de) * | 1977-12-30 | 1986-10-09 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe und deren Verwendung |
| DE3007518A1 (de) * | 1980-02-28 | 1981-09-17 | Cassella Ag, 6000 Frankfurt | Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und verwendung zum faerben und bedrucken von synthetischem, hydrophobem fasermaterial |
| US4400318A (en) * | 1980-05-19 | 1983-08-23 | Eastman Kodak Company | Substituted 5-acyl-3-carbamoyl-2-thienyl azo dyes with aniline, tetrahydroquinoline, and benzomorpholine couplers, process of manufacture, and polyamide testile materials dyed therewith |
| JPS57141451A (en) * | 1981-02-26 | 1982-09-01 | Sumitomo Chem Co Ltd | Monoazo dye and production thereof |
| US4385104A (en) | 1981-04-29 | 1983-05-24 | Eastman Kodak Company | Photographic products and processes employing novel nondiffusible 6-(2-thienylazo)-3-pyridinol cyan dye-releasing compounds and precursors thereof |
| US4396546A (en) | 1981-04-29 | 1983-08-02 | Eastman Kodak Company | Photographic products and processes employing novel nondiffusible 6-(2-thienylazo)-3-pyridinol cyan dye-releasing compounds and precursors thereof |
| JPS5922964A (ja) * | 1982-07-30 | 1984-02-06 | Hitachi Ltd | アゾ系多色性色素を含む液晶組成物 |
| JPS5924754A (ja) * | 1982-07-30 | 1984-02-08 | Gosei Senriyou Gijutsu Kenkyu Kumiai | モノアゾ化合物及びそれを用いる染色法 |
| JPS5996165A (ja) * | 1982-11-22 | 1984-06-02 | Gosei Senriyou Gijutsu Kenkyu Kumiai | 合成繊維用モノアゾ染料 |
| DE3402026A1 (de) * | 1984-01-21 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | Neue 2-aminothiophenderivate |
| US4568738A (en) * | 1984-03-19 | 1986-02-04 | Eastman Kodak Company | Thiophen-2-ylazopyrazole compounds as colorants for textile fibers |
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| CA1243669A (en) * | 1984-06-25 | 1988-10-25 | Edward W. Kluger | Reactive colorants |
| DE3507421A1 (de) * | 1985-03-02 | 1986-09-04 | Basf Ag, 6700 Ludwigshafen | Thiophenderivate |
| EP0193885B1 (de) * | 1985-03-02 | 1989-06-14 | BASF Aktiengesellschaft | Thiophenderivate |
| DE3510410A1 (de) * | 1985-03-22 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe |
| DE3512760A1 (de) * | 1985-04-10 | 1986-10-23 | Basf Ag, 6700 Ludwigshafen | Azofarbstoffe mit thiophen-diazokomponenten |
| DE3528759A1 (de) * | 1985-08-10 | 1987-02-19 | Basf Ag | Heterocyclische azofarbstoffe |
| DE3639942A1 (de) * | 1986-11-22 | 1988-06-01 | Basf Ag | Thiophenazofarbstoffe |
| US4751254A (en) * | 1987-01-20 | 1988-06-14 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| DE3876313T2 (de) * | 1987-06-29 | 1993-04-01 | Ici Plc | Dispersionsfarbstoffe. |
| US5052380A (en) * | 1989-07-07 | 1991-10-01 | Minnesota Mining And Manufacturing Company | Colored orthopedic resins and orthopedic casting materials incorporating same |
| EP0518133B1 (en) * | 1991-06-11 | 1996-04-10 | DyStar Japan Ltd. | Monoazodye |
| GB9215777D0 (en) * | 1992-07-24 | 1992-09-09 | Ici Plc | Disperse dyes |
| GB9219418D0 (en) * | 1992-09-14 | 1992-10-28 | Ici Plc | Disperse dyes |
| TW324021B (en) * | 1994-03-08 | 1998-01-01 | Daistar Japan Kk | Mono-azo dyestuff |
| KR960031548A (ko) * | 1995-02-20 | 1996-09-17 | 고사이 아키오 | 모노아조 화합물 및 이 화합물을 사용하는 소수성 섬유재료의 염색 또는 날염방법 |
| GB9515175D0 (en) * | 1995-07-24 | 1995-09-20 | Zeneca Ltd | Azothiophenes |
| GB9608489D0 (en) * | 1996-04-25 | 1996-07-03 | Zeneca Ltd | Compositions, processes and uses |
| WO2020136760A1 (ja) * | 2018-12-26 | 2020-07-02 | 緒方 健 | ソーシャルアーカイビングサービスのための方法及びシステム |
| US12195703B2 (en) * | 2020-03-02 | 2025-01-14 | Milliken & Company | Composition comprising hueing agent |
| CN112341430A (zh) * | 2020-11-11 | 2021-02-09 | 嘉禾宜事达（沈阳）化学有限公司 | 单偶氮化合物及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA895863A (en) * | 1972-03-21 | A. Weaver Max | Azo compound containing a triazolylthio group | |
| US2805218A (en) * | 1954-04-05 | 1957-09-03 | Eastman Kodak Co | 2-amino-3-nitro-5-acylthiophene azo dye compounds |
| FR1139567A (fr) * | 1954-04-05 | 1957-07-02 | Eastman Kodak Co | Nouveaux composés azoïques, leur préparation et leurs applications |
| DE1079759B (de) * | 1954-04-05 | 1960-04-14 | Eastman Kodak Co | Verfahren zur Herstellung von Monoazofarbstoffen |
| US2825726A (en) * | 1955-08-12 | 1958-03-04 | Eastman Kodak Co | Monoazo compounds containing a 2-aminothiophene nucleus |
| US2827451A (en) * | 1955-08-12 | 1958-03-18 | Eastman Kodak Co | 2-aminothiophene azo compounds |
| US2827450A (en) * | 1955-08-12 | 1958-03-18 | Eastman Kodak Co | 2-aminothiophene azo compounds |
| JPS4633226Y1 (enrdf_load_stackoverflow) * | 1968-05-07 | 1971-11-17 | ||
| FR2008404A1 (en) * | 1968-05-13 | 1970-01-23 | Eastman Kodak Co | Insoluble monoazo dyes for polyester fibres |
| GB1351381A (en) * | 1971-01-11 | 1974-04-24 | Ici Ltd | Disperse azo dyestuffs |
| GB1351382A (en) * | 1971-01-11 | 1974-04-24 | Ici Ltd | Disperse azo dyestuffs |
-
1972
- 1972-01-28 GB GB404672A patent/GB1394365A/en not_active Expired
-
1973
- 1973-01-18 CA CA161,747A patent/CA993866A/en not_active Expired
- 1973-01-18 CA CA161,746A patent/CA993865A/en not_active Expired
- 1973-01-18 CA CA161,748A patent/CA993867A/en not_active Expired
- 1973-01-23 BE BE794417D patent/BE794417A/xx not_active IP Right Cessation
- 1973-01-23 BE BE794416D patent/BE794416A/xx not_active IP Right Cessation
- 1973-01-23 BE BE794415D patent/BE794415A/xx not_active IP Right Cessation
- 1973-01-24 IT IT1954573A patent/IT983417B/it active
- 1973-01-24 IT IT1954773A patent/IT983419B/it active
- 1973-01-24 IT IT1954673A patent/IT983418B/it active
- 1973-01-25 NL NL7301076A patent/NL7301076A/xx not_active Application Discontinuation
- 1973-01-25 NL NL7301077A patent/NL178083C/xx not_active IP Right Cessation
- 1973-01-25 NL NL7301081A patent/NL173656C/xx not_active IP Right Cessation
- 1973-01-25 NL NL7301078A patent/NL7301078A/xx not_active Application Discontinuation
- 1973-01-26 BR BR64373A patent/BR7300643D0/pt unknown
- 1973-01-26 CH CH118273A patent/CH569057A5/xx not_active IP Right Cessation
- 1973-01-26 BR BR63773A patent/BR7300637D0/pt unknown
- 1973-01-26 FR FR7302870A patent/FR2169343B1/fr not_active Expired
- 1973-01-26 CH CH118473A patent/CH572080A5/xx not_active IP Right Cessation
- 1973-01-26 FR FR7302873A patent/FR2169346B1/fr not_active Expired
- 1973-01-26 CH CH118373A patent/CH572079A5/xx not_active IP Right Cessation
- 1973-01-26 FR FR7302871A patent/FR2169344B1/fr not_active Expired
- 1973-01-26 CH CH118573A patent/CH575409A5/xx not_active IP Right Cessation
- 1973-01-26 FR FR7302872A patent/FR2169345B1/fr not_active Expired
- 1973-01-26 BR BR64173A patent/BR7300641D0/pt unknown
- 1973-01-27 ES ES411051A patent/ES411051A1/es not_active Expired
- 1973-01-27 ES ES411052A patent/ES411052A1/es not_active Expired
- 1973-01-27 ES ES411050A patent/ES411050A1/es not_active Expired
- 1973-01-27 ES ES411049A patent/ES411049A1/es not_active Expired
- 1973-01-29 JP JP1179573A patent/JPS5532740B2/ja not_active Expired
- 1973-01-29 JP JP1179773A patent/JPS5518710B2/ja not_active Expired
- 1973-01-29 DE DE19732304218 patent/DE2304218C2/de not_active Expired
- 1973-01-29 JP JP1179473A patent/JPS5747214B2/ja not_active Expired
- 1973-01-29 JP JP1179673A patent/JPS5640177B2/ja not_active Expired
- 1973-01-29 DE DE19732304202 patent/DE2304202C2/de not_active Expired
- 1973-01-29 DE DE19732304203 patent/DE2304203C2/de not_active Expired
- 1973-01-29 DE DE19732304201 patent/DE2304201C2/de not_active Expired
- 1973-04-23 BE BE794418A patent/BE794418A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2304218C2 (de) | Disperse Azofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen Textilmaterialien | |
| EP0555179B1 (de) | Azofarbstoffe | |
| DE2201112C2 (de) | Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien | |
| DE1932810C3 (de) | Wasserunlösliche Monoazofarbstoffe und Verfahren zu deren Herstellung | |
| DE1644112B2 (de) | Von sauren wasserloeslichmachenden gruppen freie, basische monoazofarbstoffe | |
| DE2201113C2 (de) | "Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von synthetischen organischen Textilmaterialien" | |
| DE2325391A1 (de) | Azofarbstoffe | |
| DE2333828A1 (de) | Azofarbstoffe | |
| DE2850994C2 (enrdf_load_stackoverflow) | ||
| DE2434207C2 (de) | In Wasser schwer lösliche Monoazoverbindungen, ihre Herstellung und Verwendung | |
| DE2241259C3 (de) | 1,2,4-Benzotriazinuin-Farbstoffe, Verfahren zu ihrer Herstellung und Verfahren zum Färben und Bedrucken | |
| CH645663A5 (de) | Verfahren zur herstellung von chlorzinksalzen von thiazoliumazofarbstoffen. | |
| EP0017621A1 (de) | Naphtholactamverbindungen, Verfahren zu deren Herstellung sowie ihre Verwendung als Farbstoffe | |
| DE3016301A1 (de) | Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2130992C3 (de) | Wasserunlösliche Monoazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben | |
| DE2849995C3 (de) | Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2525557A1 (de) | Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2453209A1 (de) | Disazofarbstoffe | |
| DE1079759B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE1922901C3 (de) | Azofarbstoffe, enthaltend einen Sulfolanylpyrazolrest | |
| DE2920590A1 (de) | Azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben von synthetischen polymeren | |
| DE1644281C3 (de) | Wasserunlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE2437274A1 (de) | Neue, wasserunloesliche azofarbstoffe und verfahren zu ihrer herstellung | |
| DE2101999A1 (de) | Farbstoffe | |
| DE2104563A1 (de) | Neue Azoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |