GB1583377A - Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde - Google Patents
Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde Download PDFInfo
- Publication number
- GB1583377A GB1583377A GB17133/77A GB1713377A GB1583377A GB 1583377 A GB1583377 A GB 1583377A GB 17133/77 A GB17133/77 A GB 17133/77A GB 1713377 A GB1713377 A GB 1713377A GB 1583377 A GB1583377 A GB 1583377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- optionally substituted
- dyestuffs
- alkyl
- hydrogen
- lower 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
- QFBSIUIFNVITOR-UHFFFAOYSA-N 5-aminothiophene-2-carbaldehyde Chemical compound NC1=CC=C(C=O)S1 QFBSIUIFNVITOR-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000000975 dye Substances 0.000 claims abstract description 13
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- -1 2-amino-3-nitro-5-formyl N-phenylmorpholine Chemical compound 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 238000005859 coupling reaction Methods 0.000 claims description 28
- 230000008878 coupling Effects 0.000 claims description 27
- 238000010168 coupling process Methods 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 239000004753 textile Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 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 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229920002994 synthetic fiber Polymers 0.000 claims description 10
- 239000004758 synthetic textile Substances 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- YSNMMQRIPFUHAO-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carbonitrile Chemical compound CCN1C(O)=C(C#N)C(C)=CC1=O YSNMMQRIPFUHAO-UHFFFAOYSA-N 0.000 claims description 3
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 3
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 3
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000012505 colouration Methods 0.000 claims description 3
- 101150111293 cor-1 gene Proteins 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 244000172533 Viola sororia Species 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- CRWPRTSATHQOHM-UHFFFAOYSA-N 5-amino-4-nitrothiophene-2-carbaldehyde Chemical compound NC=1SC(C=O)=CC=1[N+]([O-])=O CRWPRTSATHQOHM-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- VDDXRGXGWQSXGX-UHFFFAOYSA-N 2-amino-5-formylthiophene-3-carbonitrile Chemical compound NC=1SC(C=O)=CC=1C#N VDDXRGXGWQSXGX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000974482 Aricia saepiolus Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
- 150000004793 2,6-dihydroxypyridines Chemical class 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- GQTVFFSGTYGONS-UHFFFAOYSA-N 2-acetamidothiophene-3-carboxamide Chemical compound CC(=O)NC=1SC=CC=1C(N)=O GQTVFFSGTYGONS-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 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 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-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
- 150000005003 1-naphthylamines Chemical class 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
- NDELSWXIAJLWOU-UHFFFAOYSA-N 2,5-dimethyl-4h-pyrazol-3-one Chemical compound CN1N=C(C)CC1=O NDELSWXIAJLWOU-UHFFFAOYSA-N 0.000 description 1
- PZPNAFLQWAIPPG-UHFFFAOYSA-N 2,6-bis(2-methoxyethylamino)-4-methylpyridine-3-carbonitrile Chemical compound COCCNC1=CC(C)=C(C#N)C(NCCOC)=N1 PZPNAFLQWAIPPG-UHFFFAOYSA-N 0.000 description 1
- AZRKRYOJEUTHER-UHFFFAOYSA-N 2-amino-5-formyl-4-methylthiophene-3-carbonitrile Chemical compound CC1=C(C=O)SC(N)=C1C#N AZRKRYOJEUTHER-UHFFFAOYSA-N 0.000 description 1
- WHZIZZOTISTHCT-UHFFFAOYSA-N 2-aminothiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1N WHZIZZOTISTHCT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- PTZXZASFWKTQFA-UHFFFAOYSA-N 5-amino-3-methyl-4-nitrothiophene-2-carbaldehyde Chemical compound NC=1SC(=C(C1[N+](=O)[O-])C)C=O PTZXZASFWKTQFA-UHFFFAOYSA-N 0.000 description 1
- FMKMKBLHMONXJM-UHFFFAOYSA-N 5-methyl-2-phenylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC=C1 FMKMKBLHMONXJM-UHFFFAOYSA-N 0.000 description 1
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 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 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 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
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- CIPVVROJHKLHJI-UHFFFAOYSA-N n,n-diethyl-3-methylaniline Chemical compound CCN(CC)C1=CC=CC(C)=C1 CIPVVROJHKLHJI-UHFFFAOYSA-N 0.000 description 1
- PJFIAKRRJLGWMD-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(OC)C(NC(=O)CC(C)=O)=C1 PJFIAKRRJLGWMD-UHFFFAOYSA-N 0.000 description 1
- DNZYKTPWSIPDAA-UHFFFAOYSA-N n-(3-cyano-4-methylthiophen-2-yl)acetamide Chemical compound CC(=O)NC=1SC=C(C)C=1C#N DNZYKTPWSIPDAA-UHFFFAOYSA-N 0.000 description 1
- YZTCKWNIDZKISC-UHFFFAOYSA-N n-(5-formyl-3-nitrothiophen-2-yl)acetamide Chemical compound CC(=O)NC=1SC(C=O)=CC=1[N+]([O-])=O YZTCKWNIDZKISC-UHFFFAOYSA-N 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
- VIACAIAQHPLINF-UHFFFAOYSA-N n-benzyl-n-ethyl-3-methylaniline Chemical compound C=1C=CC(C)=CC=1N(CC)CC1=CC=CC=C1 VIACAIAQHPLINF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FSATURPVOMZWBY-UHFFFAOYSA-N n-thiophen-2-ylacetamide Chemical compound CC(=O)NC1=CC=CS1 FSATURPVOMZWBY-UHFFFAOYSA-N 0.000 description 1
- 238000005648 named reaction Methods 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C09B29/0025—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17133/77A GB1583377A (en) | 1977-04-25 | 1977-04-25 | Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde |
| IT22675/78A IT1094933B (it) | 1977-04-25 | 1978-04-24 | Coloranti azoici a dispersione |
| CH440178A CH631197A5 (en) | 1977-04-25 | 1978-04-24 | Dispersion dyes of the monoazo series |
| FR7812094A FR2388860A1 (fr) | 1977-04-25 | 1978-04-24 | Colorants monoazoiques disperses et leur procede de fabrication |
| JP4920378A JPS53146731A (en) | 1977-04-25 | 1978-04-24 | Dispersed monoazo dye having no sulfonic acid group* method of making same and dyeing process for synthetic fiber material |
| DE19782818101 DE2818101A1 (de) | 1977-04-25 | 1978-04-25 | Monoazodispersionsfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben von synthetischen textilmaterialien |
| ES469122A ES469122A1 (es) | 1977-04-25 | 1978-04-25 | Procedimiento para preparar colorantes monoazoicos disper- sos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17133/77A GB1583377A (en) | 1977-04-25 | 1977-04-25 | Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1583377A true GB1583377A (en) | 1981-01-28 |
Family
ID=10089872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17133/77A Expired GB1583377A (en) | 1977-04-25 | 1977-04-25 | Disperse azo dyestuffs derived from a 2-aminothiophene-5-aldehyde |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS53146731A (it) |
| CH (1) | CH631197A5 (it) |
| DE (1) | DE2818101A1 (it) |
| ES (1) | ES469122A1 (it) |
| FR (1) | FR2388860A1 (it) |
| GB (1) | GB1583377A (it) |
| IT (1) | IT1094933B (it) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| US4751288A (en) * | 1985-04-10 | 1988-06-14 | Basf Aktiengesellschaft | Azo dyes containing 2-amino-3-cyano-5-formylthiophene derivatives as diazo components and substituted aniline compounds as coupling components |
| US4751254A (en) * | 1987-01-20 | 1988-06-14 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| US4820809A (en) * | 1984-07-24 | 1989-04-11 | Basf Aktiengesellschaft | Heterocyclic azo dyes |
| US4912203A (en) * | 1984-06-25 | 1990-03-27 | Milliken Research Corporation | Thiophene base colorants useful for coloring thermoset resins |
| US5052380A (en) * | 1989-07-07 | 1991-10-01 | Minnesota Mining And Manufacturing Company | Colored orthopedic resins and orthopedic casting materials incorporating same |
| US5206375A (en) * | 1985-03-02 | 1993-04-27 | Basf Aktiengesellschaft | Thiophene derivatives |
| US5466790A (en) * | 1992-05-12 | 1995-11-14 | Basf Aktiengesellschaft | Azo dyes with an acetalized diazo component of the thiophene or thiazole series |
| US5679800A (en) * | 1984-08-30 | 1997-10-21 | Clariant Finance (Bvi) Limited | 2-Amino-3,5,disubstituted-4-halothiophenes and processes for the synthesis thereof |
| US5783649A (en) * | 1995-06-13 | 1998-07-21 | Basf Aktiengesellschaft | Polymerizable azo dyes with a thiophene structure |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH644369A5 (de) | 1979-05-03 | 1984-07-31 | Sandoz Ag | 2-amino-4-chlorthiazolverbindungen. |
| DE3427200A1 (de) * | 1984-07-24 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | Methinfarbstoffe |
| US6414013B1 (en) * | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1351382A (en) * | 1971-01-11 | 1974-04-24 | Ici Ltd | Disperse azo dyestuffs |
| GB1394365A (en) * | 1972-01-28 | 1975-05-14 | Impperial Chemical Ind Ltd | Disperse azo dyestuffs |
-
1977
- 1977-04-25 GB GB17133/77A patent/GB1583377A/en not_active Expired
-
1978
- 1978-04-24 CH CH440178A patent/CH631197A5/de not_active IP Right Cessation
- 1978-04-24 JP JP4920378A patent/JPS53146731A/ja active Pending
- 1978-04-24 IT IT22675/78A patent/IT1094933B/it active
- 1978-04-24 FR FR7812094A patent/FR2388860A1/fr active Granted
- 1978-04-25 ES ES469122A patent/ES469122A1/es not_active Expired
- 1978-04-25 DE DE19782818101 patent/DE2818101A1/de not_active Ceased
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| US4912203A (en) * | 1984-06-25 | 1990-03-27 | Milliken Research Corporation | Thiophene base colorants useful for coloring thermoset resins |
| US4820809A (en) * | 1984-07-24 | 1989-04-11 | Basf Aktiengesellschaft | Heterocyclic azo dyes |
| US5679800A (en) * | 1984-08-30 | 1997-10-21 | Clariant Finance (Bvi) Limited | 2-Amino-3,5,disubstituted-4-halothiophenes and processes for the synthesis thereof |
| US5206375A (en) * | 1985-03-02 | 1993-04-27 | Basf Aktiengesellschaft | Thiophene derivatives |
| US4751288A (en) * | 1985-04-10 | 1988-06-14 | Basf Aktiengesellschaft | Azo dyes containing 2-amino-3-cyano-5-formylthiophene derivatives as diazo components and substituted aniline compounds as coupling components |
| US4751254A (en) * | 1987-01-20 | 1988-06-14 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| US5052380A (en) * | 1989-07-07 | 1991-10-01 | Minnesota Mining And Manufacturing Company | Colored orthopedic resins and orthopedic casting materials incorporating same |
| US5466790A (en) * | 1992-05-12 | 1995-11-14 | Basf Aktiengesellschaft | Azo dyes with an acetalized diazo component of the thiophene or thiazole series |
| US5783649A (en) * | 1995-06-13 | 1998-07-21 | Basf Aktiengesellschaft | Polymerizable azo dyes with a thiophene structure |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2388860A1 (fr) | 1978-11-24 |
| ES469122A1 (es) | 1978-11-16 |
| FR2388860B1 (it) | 1981-08-07 |
| IT1094933B (it) | 1985-08-10 |
| DE2818101A1 (de) | 1978-11-02 |
| CH631197A5 (en) | 1982-07-30 |
| JPS53146731A (en) | 1978-12-20 |
| IT7822675A0 (it) | 1978-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |