JPH0322426B2 - - Google Patents
Info
- Publication number
- JPH0322426B2 JPH0322426B2 JP17658581A JP17658581A JPH0322426B2 JP H0322426 B2 JPH0322426 B2 JP H0322426B2 JP 17658581 A JP17658581 A JP 17658581A JP 17658581 A JP17658581 A JP 17658581A JP H0322426 B2 JPH0322426 B2 JP H0322426B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- residue
- formula
- substituted
- sulfo
- 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
- -1 hydroxy, acetoxy Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 20
- 229910052801 chlorine Chemical group 0.000 claims description 19
- 238000004043 dyeing Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000000460 chlorine Chemical group 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004958 1,4-naphthylene group Chemical group 0.000 claims description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- WMSQJZHVGMMPQT-UHFFFAOYSA-N n-chlorobenzamide Chemical compound ClNC(=O)C1=CC=CC=C1 WMSQJZHVGMMPQT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000005521 carbonamide group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000005977 Ethylene Substances 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 4
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 description 28
- 230000008878 coupling Effects 0.000 description 27
- 238000010168 coupling process Methods 0.000 description 27
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 239000000975 dye Substances 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000985 reactive dye Substances 0.000 description 9
- 210000002268 wool Anatomy 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000002657 fibrous material Substances 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 239000004753 textile Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- QJHGFCIORJWYAL-UHFFFAOYSA-N 2-(3-chloroanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC=CC(Cl)=C1 QJHGFCIORJWYAL-UHFFFAOYSA-N 0.000 description 2
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IQVSWLPEOQMCQD-UHFFFAOYSA-N n-phenylethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC=C1 IQVSWLPEOQMCQD-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000000865 phosphorylative effect Effects 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-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
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
- LJBFLYWSZMMMAR-UHFFFAOYSA-N 2-(2,5-dichloroanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC(Cl)=CC=C1Cl LJBFLYWSZMMMAR-UHFFFAOYSA-N 0.000 description 1
- NGNZQZBUFVCPRZ-UHFFFAOYSA-N 2-(2-chloro-5-methoxyanilino)ethanesulfonic acid Chemical compound COC1=CC=C(Cl)C(NCCS(O)(=O)=O)=C1 NGNZQZBUFVCPRZ-UHFFFAOYSA-N 0.000 description 1
- NJYFGWKFNYUWLZ-UHFFFAOYSA-N 2-(2-chloroanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC=CC=C1Cl NJYFGWKFNYUWLZ-UHFFFAOYSA-N 0.000 description 1
- ZVUYDGOVNZGWSX-UHFFFAOYSA-N 2-(2-methoxyanilino)ethanesulfonic acid Chemical compound COC1=CC=CC=C1NCCS(O)(=O)=O ZVUYDGOVNZGWSX-UHFFFAOYSA-N 0.000 description 1
- ARTRSIWXLHBPAK-UHFFFAOYSA-N 2-(2-methylanilino)ethanesulfonic acid Chemical compound CC1=CC=CC=C1NCCS(O)(=O)=O ARTRSIWXLHBPAK-UHFFFAOYSA-N 0.000 description 1
- ZBQIMMIPACUIIO-UHFFFAOYSA-N 2-(5-chloro-2-methoxyanilino)ethanesulfonic acid Chemical compound COC1=CC=C(Cl)C=C1NCCS(O)(=O)=O ZBQIMMIPACUIIO-UHFFFAOYSA-N 0.000 description 1
- WIFRLFONBQCGMD-UHFFFAOYSA-N 2-(5-chloro-2-methoxyanilino)propane-1-sulfonic acid Chemical compound COC1=CC=C(Cl)C=C1NC(C)CS(O)(=O)=O WIFRLFONBQCGMD-UHFFFAOYSA-N 0.000 description 1
- MVNNTWPUWHVQDC-UHFFFAOYSA-N 2-(5-chloro-2-methylanilino)ethanesulfonic acid Chemical compound CC1=CC=C(Cl)C=C1NCCS(O)(=O)=O MVNNTWPUWHVQDC-UHFFFAOYSA-N 0.000 description 1
- CWFPKZDXYSTRPE-UHFFFAOYSA-N 2-(5-chloro-n-ethyl-2-methoxyanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)C1=CC(Cl)=CC=C1OC CWFPKZDXYSTRPE-UHFFFAOYSA-N 0.000 description 1
- SDMCKIUVIVHZSU-UHFFFAOYSA-N 2-(n-benzylanilino)ethanesulfonic acid Chemical compound C=1C=CC=CC=1N(CCS(=O)(=O)O)CC1=CC=CC=C1 SDMCKIUVIVHZSU-UHFFFAOYSA-N 0.000 description 1
- SVDAGORERCSAIV-UHFFFAOYSA-N 2-(n-ethyl-3-methylanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)C1=CC=CC(C)=C1 SVDAGORERCSAIV-UHFFFAOYSA-N 0.000 description 1
- YAFMKTJYVTZOCF-UHFFFAOYSA-N 2-(n-ethylanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)C1=CC=CC=C1 YAFMKTJYVTZOCF-UHFFFAOYSA-N 0.000 description 1
- KYQSQCLRQWXHLX-UHFFFAOYSA-N 2-(n-methylanilino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(C)C1=CC=CC=C1 KYQSQCLRQWXHLX-UHFFFAOYSA-N 0.000 description 1
- SARHGESRKAMMJB-UHFFFAOYSA-N 2-[3-chloro-n-(2-hydroxyethyl)anilino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCO)C1=CC=CC(Cl)=C1 SARHGESRKAMMJB-UHFFFAOYSA-N 0.000 description 1
- KMGKMCIMZMXLGQ-UHFFFAOYSA-N 2-[3-chloro-n-(2-sulfoethyl)anilino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCS(O)(=O)=O)C1=CC=CC(Cl)=C1 KMGKMCIMZMXLGQ-UHFFFAOYSA-N 0.000 description 1
- WRKPLVBHLSGZOD-UHFFFAOYSA-N 2-[3-methyl-n-(2-sulfoethyl)anilino]ethanesulfonic acid Chemical compound CC1=CC=CC(N(CCS(O)(=O)=O)CCS(O)(=O)=O)=C1 WRKPLVBHLSGZOD-UHFFFAOYSA-N 0.000 description 1
- ZLOCXTVHTKNCJG-UHFFFAOYSA-N 2-[5-chloro-n-(2-hydroxyethyl)-2-methoxyanilino]ethanesulfonic acid Chemical compound COC1=CC=C(Cl)C=C1N(CCO)CCS(O)(=O)=O ZLOCXTVHTKNCJG-UHFFFAOYSA-N 0.000 description 1
- GSKTXZDTNQXZFY-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)anilino]ethanesulfonic acid Chemical compound CC(=O)OCCN(CCS(O)(=O)=O)C1=CC=CC=C1 GSKTXZDTNQXZFY-UHFFFAOYSA-N 0.000 description 1
- AQYSPKFOXVQJKF-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)anilino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCC#N)C1=CC=CC=C1 AQYSPKFOXVQJKF-UHFFFAOYSA-N 0.000 description 1
- MWMHPPRXUQLLEU-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCO)C1=CC=CC=C1 MWMHPPRXUQLLEU-UHFFFAOYSA-N 0.000 description 1
- DDZWBFMGAGSXBJ-UHFFFAOYSA-N 2-[n-(2-phenylethyl)anilino]ethanesulfonic acid Chemical compound C=1C=CC=CC=1N(CCS(=O)(=O)O)CCC1=CC=CC=C1 DDZWBFMGAGSXBJ-UHFFFAOYSA-N 0.000 description 1
- CRROEVUWXPRFEL-UHFFFAOYSA-N 2-[n-(2-sulfoethyl)anilino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCS(O)(=O)=O)C1=CC=CC=C1 CRROEVUWXPRFEL-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- QYDPAMRPXAQAIL-UHFFFAOYSA-N 2-anilinopropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)NC1=CC=CC=C1 QYDPAMRPXAQAIL-UHFFFAOYSA-N 0.000 description 1
- VSPCBVLMZOOVIC-UHFFFAOYSA-N 2-chloro-5-(2-chloroethylsulfonyl)aniline Chemical compound NC1=CC(S(=O)(=O)CCCl)=CC=C1Cl VSPCBVLMZOOVIC-UHFFFAOYSA-N 0.000 description 1
- FXKMTSIKHBYZSZ-UHFFFAOYSA-N 2-chloroethanesulfonic acid Chemical compound OS(=O)(=O)CCCl FXKMTSIKHBYZSZ-UHFFFAOYSA-N 0.000 description 1
- JYVVXBDNAPHKAI-UHFFFAOYSA-N 2-hydroxy-n-phenylethanesulfonamide Chemical compound OCCS(=O)(=O)NC1=CC=CC=C1 JYVVXBDNAPHKAI-UHFFFAOYSA-N 0.000 description 1
- IAVHKMVGTPXJIC-UHFFFAOYSA-N 2-phenylamino-ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC=CC=C1 IAVHKMVGTPXJIC-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BIOZLVVJWHHFCC-UHFFFAOYSA-N 3-(2,5-dichloroanilino)-2-hydroxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(O)CNC1=CC(Cl)=CC=C1Cl BIOZLVVJWHHFCC-UHFFFAOYSA-N 0.000 description 1
- KXNHIUJDFMKYEF-UHFFFAOYSA-N 3-(2,5-dichloroanilino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNC1=CC(Cl)=CC=C1Cl KXNHIUJDFMKYEF-UHFFFAOYSA-N 0.000 description 1
- RDSHGWGARISYCR-UHFFFAOYSA-N 3-(2-chloro-3-methylanilino)-2-hydroxypropane-1-sulfonic acid Chemical compound CC1=CC=CC(NCC(O)CS(O)(=O)=O)=C1Cl RDSHGWGARISYCR-UHFFFAOYSA-N 0.000 description 1
- XRYOVGDNVGKGSO-UHFFFAOYSA-N 3-(2-chloroanilino)-2-hydroxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(O)CNC1=CC=CC=C1Cl XRYOVGDNVGKGSO-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- SJNUGHSZLOWTNL-UHFFFAOYSA-N 3-(3-chloro-n-(2-hydroxy-3-sulfopropyl)anilino)-2-hydroxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(O)CN(CC(O)CS(O)(=O)=O)C1=CC=CC(Cl)=C1 SJNUGHSZLOWTNL-UHFFFAOYSA-N 0.000 description 1
- NYMIKEADHMJESK-UHFFFAOYSA-N 3-(3-chloro-n-(2-hydroxy-3-sulfopropyl)anilino)propanoic acid Chemical compound OS(=O)(=O)CC(O)CN(CCC(O)=O)C1=CC=CC(Cl)=C1 NYMIKEADHMJESK-UHFFFAOYSA-N 0.000 description 1
- XHBUANLZLPWZJM-UHFFFAOYSA-N 3-(3-chloroanilino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNC1=CC=CC(Cl)=C1 XHBUANLZLPWZJM-UHFFFAOYSA-N 0.000 description 1
- QSXUZPGROGCKLX-UHFFFAOYSA-N 3-(5-chloro-2-methylanilino)propane-1-sulfonic acid Chemical compound CC1=CC=C(Cl)C=C1NCCCS(O)(=O)=O QSXUZPGROGCKLX-UHFFFAOYSA-N 0.000 description 1
- IBSUMVZKDLDAEK-UHFFFAOYSA-N 3-(n-ethyl-3-methylanilino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCN(CC)C1=CC=CC(C)=C1 IBSUMVZKDLDAEK-UHFFFAOYSA-N 0.000 description 1
- LHZMSRLULDAWLM-UHFFFAOYSA-N 3-(n-ethylanilino)-2-hydroxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(O)CN(CC)C1=CC=CC=C1 LHZMSRLULDAWLM-UHFFFAOYSA-N 0.000 description 1
- NYLUYMWPXIIXDX-UHFFFAOYSA-N 3-(phenylazaniumyl)propane-1-sulfonate Chemical compound OS(=O)(=O)CCCNC1=CC=CC=C1 NYLUYMWPXIIXDX-UHFFFAOYSA-N 0.000 description 1
- JTPLQOAZXUQHCI-UHFFFAOYSA-N 3-[3-chloro-n-(2-sulfoethyl)anilino]propanoic acid Chemical compound OC(=O)CCN(CCS(O)(=O)=O)C1=CC=CC(Cl)=C1 JTPLQOAZXUQHCI-UHFFFAOYSA-N 0.000 description 1
- PYAPLLCOACDKJU-UHFFFAOYSA-N 3-[n-(2-sulfoethyl)anilino]propanoic acid Chemical compound OC(=O)CCN(CCS(O)(=O)=O)C1=CC=CC=C1 PYAPLLCOACDKJU-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- CLEVULOKVPBHCU-UHFFFAOYSA-N 3-anilino-2-hydroxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(O)CNC1=CC=CC=C1 CLEVULOKVPBHCU-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- RNYWVMACDMKCTM-UHFFFAOYSA-N 4-(2-anilinoethyl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1CCNC1=CC=CC=C1 RNYWVMACDMKCTM-UHFFFAOYSA-N 0.000 description 1
- DZOKLJWXKPFVNX-UHFFFAOYSA-N 4-(2-chloroethylsulfonyl)aniline Chemical compound NC1=CC=C(S(=O)(=O)CCCl)C=C1 DZOKLJWXKPFVNX-UHFFFAOYSA-N 0.000 description 1
- MIJGJJKVYCRQNI-UHFFFAOYSA-N 4-ethenylsulfonylaniline Chemical compound NC1=CC=C(S(=O)(=O)C=C)C=C1 MIJGJJKVYCRQNI-UHFFFAOYSA-N 0.000 description 1
- MZQBTOQTTSJPBT-UHFFFAOYSA-N 6-ethenylsulfonyl-1,3-benzothiazol-2-amine Chemical compound C1=C(S(=O)(=O)C=C)C=C2SC(N)=NC2=C1 MZQBTOQTTSJPBT-UHFFFAOYSA-N 0.000 description 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
- 239000002585 base Substances 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
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BYPHZHGVWNKAFC-UHFFFAOYSA-N ethenesulfonyl fluoride Chemical compound FS(=O)(=O)C=C BYPHZHGVWNKAFC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical group OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- REUFZACIJMPYOK-UHFFFAOYSA-N n-(2-phenylethyl)aniline Chemical compound C=1C=CC=CC=1NCCC1=CC=CC=C1 REUFZACIJMPYOK-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical group [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3041891 | 1980-11-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57111359A JPS57111359A (en) | 1982-07-10 |
| JPH0322426B2 true JPH0322426B2 (enrdf_load_stackoverflow) | 1991-03-26 |
Family
ID=6116123
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17658581A Granted JPS57111359A (en) | 1980-11-06 | 1981-11-05 | Water-soluble disazo compound, manufacture and use as dye |
| JP17658481A Granted JPS57115460A (en) | 1980-11-06 | 1981-11-05 | Water-soluble monoazo compound, manufacture and use as dye |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17658481A Granted JPS57115460A (en) | 1980-11-06 | 1981-11-05 | Water-soluble monoazo compound, manufacture and use as dye |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS57111359A (enrdf_load_stackoverflow) |
| IN (1) | IN156477B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3717814A1 (de) * | 1987-05-27 | 1988-12-08 | Bayer Ag | Reaktivfarbstoffe |
| JP6401289B2 (ja) * | 2014-04-01 | 2018-10-10 | アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング | ビスアゾ染料類及びそれらの混合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653478C3 (de) * | 1976-11-25 | 1980-03-06 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Farbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben und Bedrucken von Cellulose- und Polyamidfasermaterialien |
-
1981
- 1981-10-30 IN IN1212/CAL/81A patent/IN156477B/en unknown
- 1981-11-05 JP JP17658581A patent/JPS57111359A/ja active Granted
- 1981-11-05 JP JP17658481A patent/JPS57115460A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57111359A (en) | 1982-07-10 |
| JPH0322425B2 (enrdf_load_stackoverflow) | 1991-03-26 |
| IN156477B (enrdf_load_stackoverflow) | 1985-08-10 |
| JPS57115460A (en) | 1982-07-17 |
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