DEF0015484MA - - Google Patents
Info
- Publication number
- DEF0015484MA DEF0015484MA DEF0015484MA DE F0015484M A DEF0015484M A DE F0015484MA DE F0015484M A DEF0015484M A DE F0015484MA
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- leuco
- stirred
- mixture
- 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.)
- Active
Links
- 235000002639 sodium chloride Nutrition 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 239000000984 vat dye Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 14
- -1 ester salts Chemical class 0.000 claims description 13
- NXYNTHCSPIVNNX-SAIUNTKASA-N leucoester Natural products CCCCCCCCCCCCCCCC(=CCOC(=O)CCC[C@H](C)CCC[C@H](C)CCC(C)C)C NXYNTHCSPIVNNX-SAIUNTKASA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- VTYRPALGSNDUQQ-UHFFFAOYSA-N 2-(dimethylamino)acetyl chloride Chemical compound CN(C)CC(Cl)=O VTYRPALGSNDUQQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 3
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 claims 2
- 150000001649 bromium compounds Chemical class 0.000 claims 1
- 238000009938 salting Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QMWGSOMVXSRXQX-UHFFFAOYSA-N 3-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1 QMWGSOMVXSRXQX-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- VRHSKNLJTFSZHK-UHFFFAOYSA-N 2-chloro-2-sulfoacetic acid Chemical compound OC(=O)C(Cl)S(O)(=O)=O VRHSKNLJTFSZHK-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- HUGACAUYNJDGTB-ISLYRVAYSA-N (2e)-5-chloro-2-(5-chloro-7-methyl-3-oxo-1-benzothiophen-2-ylidene)-7-methyl-1-benzothiophen-3-one Chemical compound S1C=2C(C)=CC(Cl)=CC=2C(=O)\C1=C(C1=O)/SC2=C1C=C(Cl)C=C2C HUGACAUYNJDGTB-ISLYRVAYSA-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
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 description 1
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NAJSRBSTKPARDW-UHFFFAOYSA-N C1=CC=CC=2CC3=CC=CC=C3C(C12)=O.N1N=CC=C1.C1=CC=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23 Chemical compound C1=CC=CC=2CC3=CC=CC=C3C(C12)=O.N1N=CC=C1.C1=CC=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23 NAJSRBSTKPARDW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DEF0015484MA (enExample) | ||
| DE1064661B (de) | Verfahren zur Herstellung von basischen Phthalocyaninfarbstoffen | |
| DE967136C (de) | Verfahren zur Herstellung von wasserloeslichen Estersalzen von Leukokuepenfarbstoffen | |
| DE714986C (de) | Verfahren zur Herstellung von basischen Farbstoffen der Anthrachinonreihe | |
| DE1009623B (de) | Verfahren zur Herstellung von ª-oxy-1,2,5,6-tetrahydrobenzylphosphiniger Saeure bzw. deren Alkalisalzen | |
| DE1644534A1 (de) | Antrachinonfarbstoff,sowie Verfahren zu seiner Herstellung | |
| DE1154799B (de) | Verfahren zur Herstellung von 4, 5-Dichlor- und 4, 5-Dibrom-naphthalin-1, 8-dicarbonsaeureanhydrid | |
| DE976515C (de) | Verfahren zur Herstellung von wasserloeslichen Sulfochloressigestersalzen von Leukokuepenfarbstoffen | |
| DE2318783C2 (de) | Anthrachinonfarbstoffe, Verfahren zu deren Herstellung und Verwendung derselben | |
| DE545001C (de) | Verfahren zur Herstellung echter Kuepenfarbstoffe | |
| DE824815C (de) | Verfahren zur Herstellung eines sauren Wollfarbstoffs | |
| DE534658C (de) | Verfahren zur Herstellung von Farbstoffzwischenprodukten und Farbstoffen der Anthrachinonarcridonreihe | |
| DE1120043B (de) | Verfahren zur Umwandlung eines Kobaltphthalocyanins in einen Kuepenfarbstoff mit verbesserter Loeslichkeit in der Kuepe | |
| DEF0008946MA (enExample) | ||
| DE1932646B2 (de) | 1-isoalkylamino-5-alkoxy- und 5-hydroxy-anthrachinone | |
| DE936396C (de) | Verfahren zur Herstellung wasserloeslicher Dibenzothiophenderivate | |
| DE1793123A1 (de) | Neue anionische oberflaechenaktive Stoffe,Verfahren zu deren Herstellung sowie diese enthaltende kosmetische Mittel | |
| DE924095C (de) | Verfahren zur Herstellung von Thioindigoverbindungen | |
| CH316756A (de) | Verfahren zur Herstellung von wasserlöslichen Sulfochloressigestersalzen von Leuko-Küpenfarbstoffen | |
| DE564770C (de) | Verfahren zur Herstellung von Esterderivaten aus Kuepenfarbstoffen | |
| DE950948C (de) | Verfahren zur Herstellung von schwefelhaltigen Kuepenfarbstoffen | |
| DE2224063C3 (de) | Verfahren zur Herstellung von Tetra-(alkylsulfonamido)-kupferphthalocyanin | |
| DE706950C (de) | Verfahren zur Herstellung von Farbstoffen der Phthalocyaninreihe | |
| DE602125C (de) | Verfahren zur Herstellung von kernhalogenierten Isatin-ª‡-halogeniden | |
| DE61204C (de) | Verfahren zur Darstellung gelber Farbstoffe aus Dehydrothiotoluidin |