DE967327C - Process for the production of Kuepen dyes - Google Patents
Process for the production of Kuepen dyesInfo
- Publication number
- DE967327C DE967327C DEC1472D DEC0001472D DE967327C DE 967327 C DE967327 C DE 967327C DE C1472 D DEC1472 D DE C1472D DE C0001472 D DEC0001472 D DE C0001472D DE 967327 C DE967327 C DE 967327C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- halogen
- production
- dyeing
- parts
- 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 10
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000004043 dyeing Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000000984 vat dye Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000001559 benzoic acids Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004061 bleaching Methods 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- VPHHJAOJUJHJKD-UHFFFAOYSA-N 3,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1 VPHHJAOJUJHJKD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- NJAKCIUOTIPYED-UHFFFAOYSA-N 4-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(I)C=C1 NJAKCIUOTIPYED-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- -1 bromine compound Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 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 description 1
- 239000000463 material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/36—Amino acridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Küpenfarbstoffen Es wurde gefunden, daß wertvolle Küpenfarbstoffe durch Acylierung von q.-Amino,anthrachinon-2, i-(N)-benzacridonen, deren an den Acridonring angegliederter Benzolkern frei von Halogen ist, erhalten werden können, wenn man als Acylieru.ngsmittel in pa.ra-Stellung durch Halogen substituierte Benzoesäuren bzw. ihre funktionellen Derivate verwendet.Process for the production of vat dyes It has been found that valuable vat dyes by acylation of q.-amino, anthraquinone-2, i- (N) -benzacridones, whose benzene nucleus attached to the acridone ring is free of halogen if the acylating agent is substituted by halogen in the pa.ra position Benzoic acids or their functional derivatives are used.
Die dem Verfahren als Ausgangsstoffe dienenden ¢-Aminoanthrachinon-2, i - (N) -benzacridone, in denen der Bz-Kern frei von Halogen sein muß, können im Bz-Kern beispielsweise überhaupt frei von Subütituenten sein. Gemäß vorliegendem Verfahren werden zur Acylierung solcher Verbindungen para-Halogenbenzoesäuren bzw. deren funktionelle Derivate, vorzugsweise Säurehalogenide, verwendet. Unter diesen Säuren sind insbesondere solche zu erwähnen, die Chlor oder Brom in para-Stellung zur Carboxylgruppe enthalten, ferner auch solche, die neben dem genannten Halogenatom noch weitere Subs.titnenten, beispielsweise ein weiteres Halogenatom, aufweisen. Es kommen somit beisPielsweise .-Chlor-, 4-Brom-, .-Jod- und q.-Fluorbenzoesäure sowie 3, q.-Dichlorbenzoesäure in Betracht.The [-aminoanthraquinone-2] used as starting materials for the process, i - (N) -benzacridones, in which the Bz nucleus must be free of halogen, can be im For example, the Bz core should be free of sub-substituents at all. According to the present Processes are used for the acylation of such compounds para-halobenzoic acids or their functional derivatives, preferably acid halides, are used. Under these Acids should be mentioned in particular that contain chlorine or bromine in the para position contain to the carboxyl group, and also those in addition to the halogen atom mentioned still have furthersubs.titnenten, for example a further halogen atom. There are thus, for example,.-Chloro, 4-bromo-,.-Iodo and q-fluorobenzoic acid and 3, q-dichlorobenzoic acid into consideration.
Man kann das Verfahren so durchführen, daß man ein im Bz-Kern von Halogen freies 4-Aminoanthrachinon-2, i-(N)-benzacridon mit einem para- Halo,-enbenzoylhalogenid umsetzt. Hierbei arbeitet man zweckmäßig in einem indifferenten Lösungsmittel, wie Nitrobenzol oder Dichlorbenzol, und in der Wärme.The method can be carried out in such a way that one in the Bz core of Halogen-free 4-aminoanthraquinone-2, i- (N) -benzacridone with a para Halo, enbenzoyl halide implements. It is advisable to work in an inert solvent, such as Nitrobenzene or dichlorobenzene, and in the heat.
Man erhält gemäß dem Verfahren Küpenfarbstoffe, die in bekannter Weise zum Färben sowie auch zum Bedrucken der verschiedensten Werkstoffe, wie tierischer und hauptsächlich cellulosehaltiger Fasern, dienen können. Diese Farbstoffe können auch in die entsprechenden Leukoestersalze übergeführt und in dieser Form zum Färben und Drucken verwendet werden.According to the process, vat dyes are obtained in a known manner for dyeing as well as for printing on a wide variety of materials, such as animal and mainly cellulosic fibers. These dyes can also converted into the corresponding leuco ester salts and in this form for dyeing and printing can be used.
Beispiel i 6 Teile 4-Aminoanthra.chi@non-2, 1-(N)-1', 2'-(N)-benzacridon und 6 Teile p-Brombenzoylchlori-d werden in Zoo Teilen o-Dichlorbenzol während i Stunde auf 15o bis 16o1 erhitzt. Man läßt erkalten und filtriert den blauen Farbstoff ab.Example i 6 parts 4-Aminoanthra.chi@non-2, 1- (N) -1 ', 2' - (N) -benzacridone and 6 parts of p-Brombenzoylchlori-d are in zoo parts of o-dichlorobenzene during i Heated to 15o to 16o1 for an hour. It is allowed to cool and the blue dye is filtered off away.
Der Farbstoff färbt aus rotvioletter Hyd'rosulfitküpe die pflanzliche Faser in tiefen blauen Tönen mit vorzüglichen Echtheitseigenschaften. In konzentrierter Schwefelsäure löst er sich mit gelbroter Farbe.The dye stains the vegetable from the red-violet hydrosulfite vat Fiber in deep blue tones with excellent fastness properties. In concentrated Sulfuric acid dissolves with a yellow-red color.
Verwendet man an Stelle von p-Brombenzoylchlo.rid p-Chlorbenzoylchlorid im Überschuß oder in theoretischer Menge, so erhält man ebenfalls einen blauen Farbstoff mit hervorragenden Echtheiten.If p-chlorobenzoyl chloride is used instead of p-bromobenzoylchloride in excess or in a theoretical amount, a blue dye is likewise obtained with excellent fastness properties.
Etwas rotstichigere blaue Farbtöne werden erhalten, wenn man auf 4-Aminoanthrachinon 2, 1- (N) -1', 2'- (N) -benzacridon p-Fluorbenzoylchlorid einwirken läßt.Blue shades with a slightly more reddish cast are obtained when one uses 4-aminoanthraquinone 2, 1- (N) -1 ', 2'- (N) -benzacridone allows p-fluorobenzoyl chloride to act.
Beispiel 2 3,4 Teile 4-Aminoanthrachinon-2, 1-(N)-1' 2'-(l\T)-benzacridon und 3,2 Teile p-Jodbenzoylchlorid werden in 104 Teile o-Dichlorbenzol auf 14o bis 15o° erhitzt. Nach i Stunde läßt man auf Raumtemperatur abkühlen und filtriert den in blauen Nadeln kristallisierten Farbstoff ab. Er löst sich in konzentrierter Schwefelsäure mit gelbroter Farbe und färbt Baumwolle aus rotvioletter Küpe in blauen Tönen. Die klaren, kräftigen Färbungen zeichnen sich durch gute Echtheitseigenschaften aus. Beispiel 3 3 Teile 3, 4-Dichlorbenzoesäure werden mit 104 Teilen o-Dichlorbenzol, enthaltend zwei Tropfen Pyridin, verrührt. Man setzt dem Gemisch 8 Teile Thionylchlorid zu und erhitzt unter Rückfluß allmählich bis zum Sieden. Sobald die Bildung des Säurechlorids beendet ist, destilliert man das übersc'hiissige Thi,onylchlorid mit etwas Lösungsmittel ab und gibt der Lösung nach dem Abkühlen auf etwa 90° 3,4 Teile 4-Aminoanthrachinon-a, i-(N)-i',:2'-(N) -benzacricdon zu. Darauf läßt man i Stunde bei 13o bis 1401 rühren und arbeitet den Farbstoff, wie im Beispiel 2 angegeben, auf.Example 2 3.4 parts of 4-aminoanthraquinone-2, 1- (N) -1 '2' - (l \ T) -benzacridone and 3.2 parts of p-iodobenzoyl chloride are in 104 parts of o-dichlorobenzene to 14o Heated to 15o °. After 1 hour the mixture is allowed to cool to room temperature and the filter is filtered Dye crystallized in blue needles. It dissolves in concentrated sulfuric acid with yellow-red color and dyes cotton from red-violet vat in blue tones. the clear, strong colorations are characterized by good fastness properties. Example 3 3 parts of 3, 4-dichlorobenzoic acid are mixed with 104 parts of o-dichlorobenzene, containing two drops of pyridine, stirred. 8 parts of thionyl chloride are added to the mixture and gradually heated to boiling under reflux. Once the formation of the Acid chloride is complete, the excess thi, onyl chloride is distilled off with some solvent and gives the solution after cooling to about 90 ° 3.4 parts 4-Aminoanthraquinone-a, i- (N) -i ',: 2' - (N) -benzacricdon to. Leave it for an hour stir at 13o to 1401 and work the dye as indicated in Example 2, on.
Der in blauen Nadeln kristallisierte Farbstoff färbt Baumwolle aus violetter Küpe in echten blauen Tönen. Ersetzt man im Beispiel die 3, 4-Dichlorbenzoesäure durch die entsprechende Bromverbindung, so erhält man einen Farbstoff mit ähnlichen Eigenschaften.The dye crystallized in blue needles dyes cotton violet vat in real blue tones. If the 3, 4-dichlorobenzoic acid is replaced in the example with the corresponding bromine compound, a dye with similar ones is obtained Properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH967327X | 1943-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE967327C true DE967327C (en) | 1957-10-31 |
Family
ID=4550717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC1472D Expired DE967327C (en) | 1943-12-28 | 1944-11-10 | Process for the production of Kuepen dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE967327C (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE239543C (en) * | ||||
| DE652773C (en) * | 1936-03-05 | 1937-11-08 | I G Farbenindustrie Akt Ges | Process for the production of Kuepen dyes of the anthraquinone acridone series |
| DE665598C (en) * | 1936-08-15 | 1938-09-30 | I G Farbenindustrie Akt Ges | Process for the production of Kuepen dyes of the anthraquinone series |
| US2185140A (en) * | 1936-03-04 | 1939-12-26 | Gen Aniline Works Inc | Dyestuffs of the anthraquinone benzacridone series |
| DE693610C (en) * | 1937-04-28 | 1940-07-15 | I G Farbenindustrie Akt Ges | Process for the production of Kuepen dyes of the anthraquinone acridone series |
-
1944
- 1944-11-10 DE DEC1472D patent/DE967327C/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE239543C (en) * | ||||
| US2185140A (en) * | 1936-03-04 | 1939-12-26 | Gen Aniline Works Inc | Dyestuffs of the anthraquinone benzacridone series |
| DE652773C (en) * | 1936-03-05 | 1937-11-08 | I G Farbenindustrie Akt Ges | Process for the production of Kuepen dyes of the anthraquinone acridone series |
| DE665598C (en) * | 1936-08-15 | 1938-09-30 | I G Farbenindustrie Akt Ges | Process for the production of Kuepen dyes of the anthraquinone series |
| DE693610C (en) * | 1937-04-28 | 1940-07-15 | I G Farbenindustrie Akt Ges | Process for the production of Kuepen dyes of the anthraquinone acridone series |
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