CH257724A - Process for the preparation of an acidic dye of the anthraquinone series. - Google Patents
Process for the preparation of an acidic dye of the anthraquinone series.Info
- Publication number
- CH257724A CH257724A CH257724DA CH257724A CH 257724 A CH257724 A CH 257724A CH 257724D A CH257724D A CH 257724DA CH 257724 A CH257724 A CH 257724A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- dye
- anthraquinone
- acidic dye
- preparation
- Prior art date
Links
- 230000002378 acidificating effect Effects 0.000 title claims description 4
- 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 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 3
- NBDOSEUNJLCDLN-UHFFFAOYSA-N n-(4-amino-2-methylphenyl)benzamide Chemical compound CC1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 NBDOSEUNJLCDLN-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004677 Nylon Substances 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- DAQSXJRFPGVRFV-UHFFFAOYSA-N 8-amino-5-bromo-9,10-dioxoanthracene-1,7-disulfonic acid Chemical compound O=C1C2=C(Br)C=C(S(O)(=O)=O)C(N)=C2C(=O)C2=C1C=CC=C2S(O)(=O)=O DAQSXJRFPGVRFV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000009963 fulling Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 anthraquinone compounds Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GTTFJYUWPUKXJH-UHFFFAOYSA-N n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 GTTFJYUWPUKXJH-UHFFFAOYSA-N 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
- 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
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
- C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines sauren Farbstoffes der Antbrachinonreihe. Es wurde gefunden, dass man neue An- thrachinonfarbstoffe dadurch herstellen kann, dass man Anthrachinonverbindungen der all gemeinen Formel
EMI0001.0005
worin X Halogen oder Sulfo, Y Halogen und Z Wasserstoff oder Sulfo bedeuten, mit aro matischen Aminen der allgemeinen Formel
EMI0001.0009
worin R ein Arylkern und R, Wasserstoff oder Alkyl bedeuten, kondensiert, und wenn X ein Halogenatom bedeutet,
dieses in übli cher Weise durch eine Sulfogruppe ersetzt.
Die so gewonnenen Farbstoffe färben ani malische Fasern in blauen Tönen an, die gute Licht- und Nasseehtheit besitzen und sich von den Farbstoffen gemäss der schweizeri schen Patentschrift Nr. 150808 und dem U. S. A.-Patent Nr. 1927125 besonders durch eine stark gesteigerte Wralkechtheit unter scheiden.
Zur Herstellung dieser Farbstoffe werden als aroylierte aromatische Aminoverbindun- gen z. B. o-, m-, p-Benzoylamino-anilin; o-, m-, p-(ö -Chlorbenzoylmethylamino)-anilin; a-, m-, p-(p'-Toluyl-äthylamino@)-anilin; .o-, m-, p-(m'-Phenylbenzoylbutylamino)-m-, -p-, -o-toluidin; o-, m-, p-Benzoylamino-m-, -p-, -o-chloranilin und viele andere mehr ver wendet.
Zu denselben Farbstoffen gelangt man auch, wenn man die obengenannten Anthra- chinonverbindungen mit aromatischen Ami nen der allgemeinen Formel
EMI0001.0040
worin Rt Wasserstoff oder Alkyl bedeutet, zuerst kondensiert und die so erhaltenen Axylaminoanthrachinone mit aroylierenden Mitteln, wie z.
B.. Benzoylchlorid, Benzoyl- bromid, l1I#etachlorbenzoylchlorid, Phthal- säureanhydrid usw. behandelt.
Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines, sauren Farb- stoffes der Anthrachinonreihe und ist dadurch gekennzeichnet, dass man ein Salz der 1- Amino-4-brom-anthrachinon-2,8-di,sulfonsäure mit p-Benzoylamino-m-toluidin kondensiert.
Im folgenden Beispiel bedeuten Teile Ge- wichtsteile.
<I>Beispiel:</I> 13 Teile 1-amino-4-brom-anthrachinon-2,8- disulfonsaures Kalium, 12 Teile p-Benzoyl- amino-m-toluidin, 10 Teile Natriumbikarbo- nat, 0,1 Teil Kupferbronze und 0,3 Teil Kup- ferchlorür werden in 200 Teilen Wasser auf geschlämmt und unter Rühren während 3 Stunden auf 70 erhitzt.
Die blau gewordene Kondensationsmasse wird auf übliche Weise aufgearbeitet und liefert nach dem Trocknen .ein blaues Farb- stoffpulver, das. sich in Wasser mit lebhaft blauer Farbe löst. Die Lösung in konz. Schwefelsäure ist fast farblos, beim Zusatz von wenig Paraformaldehyd tritt ein Um schlag nach blaugrün ein.
Der neue Farbstoff färbt Wolle, Seide und andere tierische Fasern sowie künstliche Fasern, wie z. B. Nylon, in schönen blauen Tönen an. Die Färbungen sind von sehr guter Lichtechtheit, sehr guter Wasch- und Schweissechtheit und guter Walkechtheit.
Process for the preparation of an acidic dye of the antbrachinone series. It has been found that new anthraquinone dyes can be produced by using anthraquinone compounds of the general formula
EMI0001.0005
wherein X is halogen or sulfo, Y is halogen and Z is hydrogen or sulfo, with aromatic amines of the general formula
EMI0001.0009
where R is an aryl nucleus and R is hydrogen or alkyl, condenses, and when X is a halogen atom,
this replaced in übli cher way by a sulfo group.
The dyes obtained in this way dye ani malic fibers in blue tones, which have good light and wet fastness and differ from the dyes according to Swiss patent specification No. 150808 and US Pat. No. 1927125, in particular because of their greatly increased Wralkfastness.
To produce these dyes, the aroylated aromatic amino compounds such. B. o-, m-, p-benzoylamino-aniline; o-, m-, p- (δ-chlorobenzoylmethylamino) aniline; a-, m-, p- (p'-toluyl-ethylamino @) - aniline; .o-, m-, p- (m'-phenylbenzoylbutylamino) -m-, -p-, -o-toluidine; o-, m-, p-Benzoylamino-m-, -p-, -o-chloroaniline and many others are used.
The same dyes can also be obtained if the above-mentioned anthrachinone compounds with aromatic amines of the general formula
EMI0001.0040
wherein Rt is hydrogen or alkyl, first condensed and the axylaminoanthraquinones thus obtained with aroylating agents, such as.
B. Benzoyl chloride, benzoyl bromide, 111 # etachlorbenzoyl chloride, phthalic anhydride, etc. treated.
The present patent relates to a process for the production of an acidic dye of the anthraquinone series and is characterized in that a salt of 1-amino-4-bromo-anthraquinone-2,8-di, sulfonic acid is used with p-benzoylamino-m -toluidine condensed.
In the following example, parts mean parts by weight.
<I> Example: </I> 13 parts of 1-amino-4-bromo-anthraquinone-2,8-disulphonic acid potassium, 12 parts of p-benzoylamino-m-toluidine, 10 parts of sodium bicarbonate, 0.1 part Copper bronze and 0.3 part of copper chloride are suspended in 200 parts of water and heated to 70 for 3 hours with stirring.
The condensation mass, which has turned blue, is worked up in the usual way and, after drying, produces a blue dye powder which dissolves in water with a vivid blue color. The solution in conc. Sulfuric acid is almost colorless; if a little paraformaldehyde is added, it turns blue-green.
The new dye dyes wool, silk and other animal fibers as well as artificial fibers such as B. Nylon, in beautiful blue tones. The dyeings have very good lightfastness, very good wash and perspiration fastness and good milled fastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257724T | 1947-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH257724A true CH257724A (en) | 1948-10-31 |
Family
ID=4472314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH257724D CH257724A (en) | 1947-06-19 | 1947-06-19 | Process for the preparation of an acidic dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH257724A (en) |
-
1947
- 1947-06-19 CH CH257724D patent/CH257724A/en unknown
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