DE469249C - Process for the production of indigoid dyes - Google Patents
Process for the production of indigoid dyesInfo
- Publication number
- DE469249C DE469249C DEG67227D DEG0067227D DE469249C DE 469249 C DE469249 C DE 469249C DE G67227 D DEG67227 D DE G67227D DE G0067227 D DEG0067227 D DE G0067227D DE 469249 C DE469249 C DE 469249C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- production
- dye
- dyes
- indigoid dyes
- 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
- 239000000975 dye Substances 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- WSTRYEOEMXCRSG-UHFFFAOYSA-N 1,4-dibromoindole-2,3-dione Chemical compound C1=CC=C(Br)C2=C1N(Br)C(=O)C2=O WSTRYEOEMXCRSG-UHFFFAOYSA-N 0.000 description 1
- MHESOLAAORBNPM-UHFFFAOYSA-N 1-benzothiophene-2,3-dione Chemical compound C1=CC=C2C(=O)C(=O)SC2=C1 MHESOLAAORBNPM-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OLKNXLMMZQVMDW-UHFFFAOYSA-N O=C(C(C(N1Br)=CC=C2)=C2Br)C1=O.Cl Chemical compound O=C(C(C(N1Br)=CC=C2)=C2Br)C1=O.Cl OLKNXLMMZQVMDW-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C09B7/00—Indigoid dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von indigoiden Farbstoffen Es wurde gefunden, daß man wertvolle indigoide Farbistoffe erhält, wenn man die Halogensubstitutionsprodukte des a, i-Naphthooxythiophens mit den 2-Anilen bzw. 2-Halogeniden zyklischer o-Diketone kondensiert und die so erhaltenen Produkte geg6benenfalls halogeniert.Process for the production of indigoid dyes It has been found that valuable indigoid dyes are obtained by using the halogen substitution products of a, i-naphthooxythiophene with the 2-anilene or 2-halides of cyclic o-diketones condensed and the products thus obtained halogenated if necessary.
Die so erhaltenen Farbstoffe färben urgebeizte Baiunwolle nicht wie die Produkte der amerikanischen Patentschrift i 434983 braunen, sondern in echten Bordeaux- bis grauen Farbtönen. Beispiel i 279 Teile 5-Brom-2, i-naphthooxythiophen und 33o Teile p-Dirnethylaminoanil des 5-Chlor-7-methylthionaphthenchinons werden in .l ooo Teilen Alkohol suspendiert und zum Sieden erhitzt. Nach kurzer Zeit ist die Kondensation beendet. Der in guter Ausbeute abgeschiedene neue Farbstoff wird filtriert, gewaschen und getrocknet. Er stellt ein rotbraunes Pulver dar, das :sich in Schwefelsäure mit violetter Farbe löst, und bildet eine orangefarbene Küpe, welche; Baumwolle in Bordeauxtönen färbt, die beim Seifen etwas heller und reiner werden. Der analoge Farbstoff aus dem p-Dimethylaminoanil des Thionaphthenchinons zeigt ähnliche Eigenschaften. Beispiel z 305 Teile Dibromisatin werden in 3 ooa Teilen Chlorbenzol suspendiert und nach Zugabe von z i o Teilen Phosphorpentachlorid erhitzt. Die ientstandene Lösung von Dibromisatinchlorid wird bei 70° unter Rühren zu einer Lösung von 234 Teilen: 7-Chlora, i-naph thooxythiophen in a ooo Teilen. Chlorbenzol gegeben. Der sich sofort abscheidender Farbstoff wird filtriert, gewaschen und getrocknet. Er bildet ein braunes Pulver, das sich in Schwefelsäure mit blauer Farbe löst. Der neue Farbstoff färbt aus goldgellber Küpe Baumwolle in graubraunen Tönen, die beim Seifen heller und röter werden:. Mit. Isatimanilid :erhält man Produkte, welche die Baumwollee in gedeckten, violettroten Tönen färben.The dyestuffs obtained in this way do not dye originally stained cotton wool, unlike the products of American patent specification i 434983, but in true Bordeaux to gray shades. Example i 279 parts of 5-bromo-2, i-naphthooxythiophene and 33o parts of p-dimethylaminoanil of 5-chloro-7-methylthionaphthenquinone are suspended in 1000 parts of alcohol and heated to the boil. The condensation ends after a short time. The new dye deposited in good yield is filtered, washed and dried. It represents a red-brown powder which: dissolves in sulfuric acid with a violet color, and forms an orange-colored vat which; Cotton dyes in shades of bordeaux, which become a little lighter and purer when soapy. The analogous dye from the p-dimethylaminoanil of thionaphthenquinone shows similar properties. Example z 305 parts of dibromoisatin are suspended in 3,000 parts of chlorobenzene and, after adding 10 parts of phosphorus pentachloride, heated. The resulting solution of dibromoisatin chloride is at 70 ° with stirring to a solution of 234 parts: 7-chlorine, i-naphthooxythiophene in a thousand parts. Given chlorobenzene. The dye which separates out immediately is filtered, washed and dried. It forms a brown powder that dissolves in sulfuric acid with a blue color. The new dye dyes cotton from a golden yellow pot in gray-brown tones, which become lighter and redder when soapy. With. Isatimanilid: one obtains products which dye the cotton in muted, violet-red tones.
Beispiel 4o8 Teile des Farbstoffes aus 5-Bruma, i-Naphthooxythi:ophen und a-Isatinanilid, werden im 4 ooo Teilen Nitrobenzol suspendiert und nach Zugabe von Sao Teilen Brom während 24 Stunden langsam bis auf r8o° ierhitzt. Nachdem die Entwicklung von Bromwasserstoff aufgehört hat, läßt man erkalten, filtriert das ausgeschiedene neue Produkt ab und wäscht mit Alkohol nach. Der bromierte Farbstoff stellt ein. dunkles Pulver dar, das, sich in Schwefelsäure mit blauer Farbe löst. Er bildet eine braunstichig orange Küpe und färbt Baumwolle in grauen Tönen, die beim Entwickeln durch Seifen heller, röter werden.Example 408 parts of the dye from 5-Bruma, i-Naphthooxythi: ophen and a-isatinanilide, are suspended in 4,000 parts of nitrobenzene and after addition from Sao parts bromine during Slowly heated to 80 ° for 24 hours. After the evolution of hydrogen bromide has ceased, the mixture is left to cool and filtered the excreted new product and washes with alcohol. The brominated dye recruits. dark powder that dissolves in sulfuric acid with a blue color. It forms a brownish orange vat and dyes cotton in gray tones become lighter, redder when developing with soaps.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH469249X | 1923-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE469249C true DE469249C (en) | 1928-12-07 |
Family
ID=4515948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG67227D Expired DE469249C (en) | 1923-01-23 | 1923-05-23 | Process for the production of indigoid dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE469249C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE743675C (en) * | 1937-10-22 | 1944-01-06 | Chem Ind Basel | Process for the production of indigoid dyes |
-
1923
- 1923-05-23 DE DEG67227D patent/DE469249C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE743675C (en) * | 1937-10-22 | 1944-01-06 | Chem Ind Basel | Process for the production of indigoid dyes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE469249C (en) | Process for the production of indigoid dyes | |
| DE504016C (en) | Process for the production of Kuepen dyes of the benzanthrone series | |
| DE478738C (en) | Process for the production of orange dyes | |
| DE663314C (en) | Process for the production of indigoid dyes | |
| DE466535C (en) | Process for the production of indigoid dyes | |
| DE541267C (en) | Process for the production of Kuepen dyes | |
| DE451720C (en) | Process for the production of Kuepen dyes | |
| DE749074C (en) | Process for the production of anthraquinone dyes | |
| DE520876C (en) | Process for the production of Kuepen dyes | |
| DE237819C (en) | ||
| DE445443C (en) | Process for the production of indigoid dyes | |
| DE486517C (en) | Process for the preparation of Kuepen dyes | |
| DE498224C (en) | Process for the preparation of dyes of the anthracene series | |
| DE739049C (en) | Process for the preparation of indirubine-like dyes | |
| DE447556C (en) | Process for the preparation of Kuepen dyes | |
| DE565078C (en) | Process for the production of Kuepen dyes | |
| CH109629A (en) | Process for the production of a new vat dye. | |
| DE1065547B (en) | Process for the production of indigoid dyes | |
| CH109627A (en) | Process for the production of a new vat dye. | |
| CH109637A (en) | Process for the production of a new vat dye. | |
| CH141317A (en) | Process for the preparation of a brown vat dye. | |
| CH109638A (en) | Process for the production of a new vat dye. | |
| CH109628A (en) | Process for the production of a new vat dye. | |
| CH121345A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. | |
| CH122762A (en) | Process for the preparation of a violet vat dye of the 2-thionaphthene-2-indolindigo series. |