BE561333A - - Google Patents

Info

Publication number

BE561333A

BE561333A BE561333DA BE561333A BE 561333 A BE561333 A BE 561333A BE 561333D A BE561333D A BE 561333DA BE 561333 A BE561333 A BE 561333A

Authority

BE

Belgium

Prior art keywords

sep

acid

beta

amino

crotonic

Prior art date

Links

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• 239000000975 dye Substances 0.000 claims description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
• 229910052803 cobalt Inorganic materials 0.000 claims description 6
• 239000010941 cobalt Substances 0.000 claims description 6
• 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
• 230000000875 corresponding Effects 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 150000002790 naphthalenes Chemical class 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 238000000034 method Methods 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 150000004700 cobalt complex Chemical class 0.000 claims 1
• 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 148
• 239000002253 acid Substances 0.000 description 26
• 239000000243 solution Substances 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 150000003931 anilides Chemical class 0.000 description 11
• 210000002268 Wool Anatomy 0.000 description 7
• -1 beta-ethylamino-crotonic acid anilide Chemical compound 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 6
• 230000001808 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
• FFIJVMMYNYSGTJ-UHFFFAOYSA-N C1=CC=C2C([NH-])=CC=CC2=C1 Chemical compound C1=CC=C2C([NH-])=CC=CC2=C1 FFIJVMMYNYSGTJ-UHFFFAOYSA-N 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
• 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 230000001264 neutralization Effects 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• KTVIXTQDYHMGHF-UHFFFAOYSA-L Cobalt(II) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 229940044175 cobalt sulfate Drugs 0.000 description 3
• 229910000361 cobalt sulfate Inorganic materials 0.000 description 3
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• JGVJIRNYPQURJF-HJWRWDBZSA-N (Z)-3-(methylamino)-N-phenylbut-2-enamide Chemical compound CN\C(C)=C/C(=O)NC1=CC=CC=C1 JGVJIRNYPQURJF-HJWRWDBZSA-N 0.000 description 2
• HWMJTSDZYMEXDM-ARJAWSKDSA-N (Z)-3-(methylamino)but-2-enoic acid Chemical compound CN\C(C)=C/C(O)=O HWMJTSDZYMEXDM-ARJAWSKDSA-N 0.000 description 2
• XTPRSWPAZJPVMR-UHFFFAOYSA-N 2-hydroxyethylazanide Chemical compound [NH-]CCO XTPRSWPAZJPVMR-UHFFFAOYSA-N 0.000 description 2
• AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 2
• WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 230000002378 acidificating Effects 0.000 description 2
• 150000001868 cobalt Chemical class 0.000 description 2
• PJQDFOMVKDFESH-UHFFFAOYSA-N cobalt(2+);N-(9H-fluoren-2-yl)-N-oxidoacetamide Chemical class [Co+2].C1=CC=C2C3=CC=C(N([O-])C(=O)C)C=C3CC2=C1.C1=CC=C2C3=CC=C(N([O-])C(=O)C)C=C3CC2=C1 PJQDFOMVKDFESH-UHFFFAOYSA-N 0.000 description 2
• 150000008049 diazo compounds Chemical class 0.000 description 2
• 238000004043 dyeing Methods 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
• 238000001465 metallisation Methods 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 239000001187 sodium carbonate Substances 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• XIZLDQRMOTWJQD-DAXSKMNVSA-N (Z)-2-(butylamino)but-2-enoic acid Chemical compound CCCCN\C(=C/C)C(O)=O XIZLDQRMOTWJQD-DAXSKMNVSA-N 0.000 description 1
• DZMZBRYJCAXKPO-SEYXRHQNSA-N (Z)-3-anilino-N-phenylbut-2-enamide Chemical compound C=1C=CC=CC=1NC(=O)/C=C(/C)NC1=CC=CC=C1 DZMZBRYJCAXKPO-SEYXRHQNSA-N 0.000 description 1
• IAOZVUUQCPRLOI-UHFFFAOYSA-N 3-amino-4-hydroxy-N-phenylbenzenesulfonamide Chemical compound C1=C(O)C(N)=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 IAOZVUUQCPRLOI-UHFFFAOYSA-N 0.000 description 1
• ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
• QPRBDAGIOLBTPF-UHFFFAOYSA-N 3-amino-N-ethyl-4-hydroxybenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=C(O)C(N)=C1 QPRBDAGIOLBTPF-UHFFFAOYSA-N 0.000 description 1
• ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 1
• FDOOTBCQFJWROU-UHFFFAOYSA-N 4-amino-3-hydroxy-N-phenylbenzenesulfonamide Chemical compound C1=C(O)C(N)=CC=C1S(=O)(=O)NC1=CC=CC=C1 FDOOTBCQFJWROU-UHFFFAOYSA-N 0.000 description 1
• JPYQFYIEOUVJDU-UHFFFAOYSA-N Beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• DNSISZSEWVHGLH-UHFFFAOYSA-N Butyramide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
• ASKVAEGIVYSGNY-UHFFFAOYSA-L Cobalt(II) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 1
• 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
• LDHQCZJRKDOVOX-NSCUHMNNSA-N Crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 235000011114 ammonium hydroxide Nutrition 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• XCGBFXNVKPHVEQ-UHFFFAOYSA-N cobalt;2,3-dihydroxybutanedioic acid;ethane-1,2-diamine Chemical compound [Co].NCCN.NCCN.NCCN.OC(=O)C(O)C(O)C(O)=O XCGBFXNVKPHVEQ-UHFFFAOYSA-N 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 239000003599 detergent Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 238000009963 fulling Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• VDOUHVITQWKJCB-UHFFFAOYSA-N naphthalen-2-ylazanide Chemical compound C1=CC=CC2=CC([NH-])=CC=C21 VDOUHVITQWKJCB-UHFFFAOYSA-N 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• 230000001131 transforming Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1