PL86540B1 - - Google Patents
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- Publication number
- PL86540B1 PL86540B1 PL16489769A PL16489769A PL86540B1 PL 86540 B1 PL86540 B1 PL 86540B1 PL 16489769 A PL16489769 A PL 16489769A PL 16489769 A PL16489769 A PL 16489769A PL 86540 B1 PL86540 B1 PL 86540B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- parts
- water
- trimethylcyclohexylamine
- wzdr
- Prior art date
Links
- -1 anthraquinone compounds Chemical class 0.000 claims description 6
- ZGMQLPDXPUINCQ-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-amine Chemical compound CC1CC(N)CC(C)(C)C1 ZGMQLPDXPUINCQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZINRVIQBCHAZMM-UHFFFAOYSA-N 1-Amino-2,4-dibromoanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(Br)=C2N ZINRVIQBCHAZMM-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 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 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004285 Potassium sulphite Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940108928 copper Drugs 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 229960004643 cupric oxide Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/264—Dyes with amino groups substituted by hydrocarbon radicals sulfonated
-
- 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania zwiazków antrachinonowych o wzorze 1, w którym jeden z podstawników Rj oznacza atom wodoru, fluoru, chloru lub bromu, a drugi podstawnik Rt oznacza atom wodoru lub obydwa podstawniki Rt oznaczaja atomy chloru.Sposób wedlug wynalazku polega na tym, ze zwiazek o wzorze 2, w którym Hal oznacza atom chlorowca, a Rt ma wyzej podane znaczenie, pod¬ daje sie reakcji z 3,5,5-trójmetylocykloheksylo- amina.Reakcje prowadzi sie w znany sposób, na przy¬ klad w temperaturze 80—200°C, korzystnie 100— 150°C, zwlaszcza 110—130 °C w srodowisku orga¬ nicznym, korzystnie w obecnosci srodka wiazacego kwas.Korzystnie stosuje sie sama 3, 5, 5-trójmetylocy- kloheksyloamine jako rozpuszczalnik i ewentualnie jako srodek wiazacy kwas lub tez obojetny w sto¬ sunku do 3, 5, 5-trójmetylocykloheksyloaminy roz¬ puszczalnik wysokowrzacyr na przyklad wrzacy w temperaturze 130—220°C taki, jak mono- i dwu- chlorobenzen, dwumetyloformamid, dwumetyloace- tamid, sulfotlenek dwumetylowy, eter glikolowy, a zwlaszcza nitrobenzen.Jako srodki wiazace kwas stosuje sie na przyklad nadmiar aminy, trzeciorzedowa, malo lotna amine, bardziej zasadowa od 3, 5, 5-trójmetylocykloheksylo¬ aminy, zasadowa sól metalu, na przyklad weglan sodowy lub potasowy lub wodorotlenek metalu al- kalicznego. Jezeli to konieczne, stosuje sie kataliza¬ tor z miedzi, taki jak miedz sproszkowana, tlenek miedziawy, chlorek miedziawy, tlenek miedziowy.Produkty reakcji mozna w znany sposób, na przy¬ klad przez odparowanie, zwlaszcza pod zmniejszo¬ nym cisnieniem, destylacje z para wodna lub roz¬ cienczenie odpowiednim srodkiem, na przyklad niz¬ szym alkoholem, takim jak metanol, etanol, izopro- panol lub weglowodorem, takim jak eter naftowy, ligroina, wyodrebniac, odsaczac, ewentualnie prze¬ myc i wysuszyc.Wytworzone zwiazki o wzorze 1 sa wartosciowy¬ mi pólproduktami do wytwarzania barwników, zwlaszcza barwników rozpuszczalnych w wodzie.*Tak na przyklad mozna zastapic atom w polozeniu 2 grupa sulfonowa, przez reakcje zwiazków o wzo¬ rze 1 z rozpuszczalnym w wodzie, obojetnym zwiaz¬ kiem siarczynowym w srodowisku wodno-organicz- nym, na przyklad wodno-alkoholowym lub wodnd- -fenolowym- stosujac fenol, krezol lub mieszanine krezoli, przy czym stezony roztwór siarczynu stano¬ wi faze wodna, w temperaturze 100—150°C, zwla¬ szcza 120—130°C i pod cisnieniem.Ponizszy przyklad wyjasnia blizej sposób wedlug wynalazku.W nastepujacym przykladzie czesci oznaczaja czesci wagowe, a procenty oznaczaja procenty Wa¬ gowe. Temperatury podano w stopniach Celsjusza.Przyklad. Mieszanine 38,1 czesc l-amino-2,4- dwubromo-antrachinonu, 160 czesci 3, 5, 5-trójme^ 86 54086 540 tylocykloheksyloaminy, 25 czesci bezwodnego octa¬ nu potasowego i 0,5 czesci chlorku miedziawego ogrzewa sie tak dlugo w temperaturze 110—120°, az zniknie z tej mieszaniny produkt wyjsciowy. Na¬ stepnie rozciencza sie mase poreakcyjna metano¬ lem, odsacza na zimno osad, przemywa metanolem i nastepnie woda i suszy. Wytworzony produkt od¬ powiada wzorowi 3.Tak wytworzony zwiazek mozna poddac dalszej reakcji w nastepujacy sposób: czesci ewentualnie przekrystalizowanego produk¬ tu ogrzewa sie w autoklawie z 50 czesciami fenolu i 20 czesciami 50% roztworu siarczynu potasowego w ciagu 16 godzin w temperaturze 130°. Fenol od- destylowuje sie z para wodna i wysala barwnik, odsacza, przemywa roztworem soli, uwalnia od ewentualnie obecnych zanieczyszczen nierozpu¬ szczalnych w wodzie przez rozpuszczenie w goracej wodzie, odsacza na goraco, wysala i suszy. Tak wytworzony barwnik odpowiada wzorowi 4. PL
Claims (1)
1. Zastrzezenie patentowe Sposób wytwarzania zwiazków antrachinonowych o wzorze 1, w którym jeden z podstawników R± oznacza atom wodoru, fluoru, chloru lub bromu, a drugi podstawnik Rj oznacza atom wodoru, lub obydwa podstawniki B.± oznaczaja atom chloru, znamienny tym, ze zwiazek o wzorze 2, w którym Hal oznacza atom chlorowca, a RA ma wyzej po¬ dane znaczenie, poddaje sie reakcji z 3, 5, 5-trój- metylocykloheksyloamina. 0 NH WZdR 1 0 NH, 0 Hal WZdR 286 540 O NH WZdR 3 0 NH ^WZCJR 4 PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH512268A CH491170A (de) | 1968-04-08 | 1968-04-08 | Verfahren zur Herstellung von Anthrachinonverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL86540B1 true PL86540B1 (pl) | 1976-06-30 |
Family
ID=4288289
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL16489769A PL86540B1 (pl) | 1968-04-08 | 1969-04-05 | |
| PL13279169A PL72610B1 (pl) | 1968-04-08 | 1969-04-05 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL13279169A PL72610B1 (pl) | 1968-04-08 | 1969-04-05 |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH544796A (pl) |
| CS (2) | CS164821B2 (pl) |
| PL (2) | PL86540B1 (pl) |
-
1968
- 1968-04-08 CH CH1574769A patent/CH544796A/de not_active IP Right Cessation
- 1968-04-08 CH CH1585769A patent/CH531027A/de not_active IP Right Cessation
-
1969
- 1969-04-05 PL PL16489769A patent/PL86540B1/pl unknown
- 1969-04-05 PL PL13279169A patent/PL72610B1/pl unknown
- 1969-04-08 CS CS396069A patent/CS164821B2/cs unknown
- 1969-04-08 CS CS396373A patent/CS164824B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH531027A (de) | 1972-11-30 |
| CS164821B2 (pl) | 1975-11-28 |
| CH544796A (de) | 1974-01-15 |
| CS164824B2 (pl) | 1975-11-28 |
| PL72610B1 (pl) | 1974-08-30 |
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