CH210599A - Process for the preparation of an acidic triphenylmethane dye. - Google Patents
Process for the preparation of an acidic triphenylmethane dye.Info
- Publication number
- CH210599A CH210599A CH210599DA CH210599A CH 210599 A CH210599 A CH 210599A CH 210599D A CH210599D A CH 210599DA CH 210599 A CH210599 A CH 210599A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- acidic
- preparation
- weight
- parts
- Prior art date
Links
- 230000002378 acidificating effect Effects 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000000981 basic dye Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- RHYNBOJRMMSEJM-UHFFFAOYSA-N n-butyl-n-ethyl-3-methylaniline Chemical compound CCCCN(CC)C1=CC=CC(C)=C1 RHYNBOJRMMSEJM-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 2
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QRHXWBURLNLUPA-UHFFFAOYSA-N 3,6-dichloroxanthen-9-one Chemical compound ClC1=CC=C2C(=O)C3=CC=C(Cl)C=C3OC2=C1 QRHXWBURLNLUPA-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- -1 heterocyclic secondary Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone powder Natural products C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Verfahren zur Herstellung eines sauren Triphenylmethanfarbstoffes. Es wurde gefunden, dass man saure Farb stoffe der Triphenylmethanreihe erhält, wenn man 3.6-Dihalogenxanthone mit isocyclischen oder heterocyclischen sekundären oder ter tiären Aminen kondensiert, dann die in 3- und 6-Stellung befindlichen Halogenatome gegen die Reste von aromatischen Aminen aus tauscht und die so erhaltenen Farbstoffe sulfo- niert. Es entstehen hierbei neue saure Farb stoffe, z.
B. solche der folgenden allgemeinen Formel
EMI0001.0011
worin g. Alkyl, Y Wasserstoff oder Methyl und R Indobeste oder N-alkyl-substituierte Anilinreste bedeuten. Die neuen Farbstoffe färben die tierische Faser in violetten Tönen von guten Echtheitseigenschaften.
Gegenstand dieses Patentes ist ein Ver fahren zur Herstellung eines sauren Triphenyl- methanfarbatoffes, welches darin besteht, dass man 3.6-Dichlorxanthon mit N-Butyl-äthyl- m-toluidin kondensiert, in der so erhaltenen Verbindung die in 3- und 6-Stellung befind lichen Chloratome gegen den Rest des 1-Amino- 4-äthoxybenzols austauscht und den so gebil deten basischen Farbstoff zur Disulfonsäure sulfoniert.
Der so erhaltene neue Farbstoff färbt Wolle und Seide in klaren violetten Tönen von guten Echtheitseigenschaften. <I>Beispiel:</I> 13,3 Gewichtsteile 3.6-Diclilorxanthon, 10,0 Gewichtsteile N-Butyläthyl-m-toluidiri, 10 Gewichtsteile Phosplioroxychlorid und 8 Gewichtsteile Chlorzink werden in 75 Ge wichtsteilen Toluol unter Rückflusskühlung so lange gekocht, bis keine Salzsäure mehr abgespalten wird.
Das sich abscheidende Kon densationsprodukt wird nach Entfernung des Toluols mit 50 Gewichtsteilen 1-Amirio-4- äthoxybenzol zwei Stunden bei<B>1000</B> C ver- schmolzen. Der so entstandene violette Farb stoff wird durch Anrühren mit verdünnter Salzsäure vom Basenüberschuss befreit und nach dein Trockner) mit Schwefelsäuremono- hydrat durch mehrstündiges (z. B. vierstün diges) Erhitzen auf<B>301</B> C zur Disulfonsäure sulfoniert. Dieser Farbstoff färbt als Natrium salz Wolle und Seide in klaren violetten Tönen von guten Echtheitseigenschaften.
Es hat wahrscheinlich folgende Konstitution:
EMI0002.0014
Das als Ausgangsstoff verwendete 3.6-Dichlor- xanthon von der Formel:
EMI0002.0017
lässt sich wie folgt darstellen: 191 Gewichtsteile 2.4-Dichlorbenzoesäure, 130 Gewichtsteile m-Chlorphenol und 120 Gewichtsteile Ätzkali werden in Glegenwart von 80 Gewichtsteilen Methanol unter Rühren auf 195 C erhitzt, wobei das als Schmelz mittel dienende Methanol abdestilliert. Nach 1/,i-stündigem Nacherhitzen auf<B>1950</B> C wird Wasser zugesetzt,
ausgesäuert und unverän dertes m-Chloi-phenol mittels Wasserdampf entfernt. Die zunächst erhaltene 5.5'-Diclilot-- diphenyläther-2-carbonsäure wird in der zehn fachen Gewichtsmenge konzentrierter Schwe felsäure eine Stunde auf etwa 95<B>0</B> C erhitzt. Dabei tritt Ringschluss zum 3.6-Dicblorxan- thon ein, das durch Ausgiessen auf Eis er halten wird und sich durch Umkristalliäieren aus Alkohol oder Methanol reinigen lässt.
Process for the preparation of an acidic triphenylmethane dye. It has been found that acidic dyes of the triphenylmethane series are obtained if 3,6-dihaloxanthones are condensed with isocyclic or heterocyclic secondary or tertiary amines, then the halogen atoms in the 3- and 6-positions are exchanged for the residues of aromatic amines and the thus obtained dyes sulfonated. This creates new acidic dyes such.
B. those of the following general formula
EMI0001.0011
wherein g. Alkyl, Y denotes hydrogen or methyl and R denotes indo groups or N-alkyl-substituted aniline groups. The new dyes dye the animal fibers in violet shades with good fastness properties.
The subject of this patent is a process for the production of an acidic triphenyl methane dye, which consists in condensing 3,6-dichloroxanthone with n-butyl-ethyl-m-toluidine, the compound thus obtained being in the 3- and 6-positions Union chlorine atoms exchanged for the remainder of the 1-amino-4-ethoxybenzene and sulfonated the so gebil Deten basic dye to disulfonic acid.
The new dye thus obtained dyes wool and silk in clear purple tones with good fastness properties. <I> Example: </I> 13.3 parts by weight of 3.6-diclilorxanthone, 10.0 parts by weight of n-butylethyl-m-toluidiri, 10 parts by weight of phosphorus oxychloride and 8 parts by weight of zinc chloride are refluxed in 75 parts by weight of toluene until none Hydrochloric acid is split off more.
The condensation product which separates out is melted after removal of the toluene with 50 parts by weight of 1-amirio-4-ethoxybenzene at 1000 C for two hours. The resulting violet dye is freed from excess base by stirring with dilute hydrochloric acid and, after drying, is sulfonated with sulfuric acid monohydrate by heating at 301 C for several hours (e.g. four hours) to form disulfonic acid. As sodium salt, this dye dyes wool and silk in clear purple tones with good fastness properties.
It probably has the following constitution:
EMI0002.0014
The 3.6-dichloro xanthone used as the starting material has the formula:
EMI0002.0017
can be represented as follows: 191 parts by weight of 2,4-dichlorobenzoic acid, 130 parts by weight of m-chlorophenol and 120 parts by weight of caustic potash are heated in the presence of 80 parts by weight of methanol with stirring to 195 ° C., the methanol used as a melting agent being distilled off. After 1 /, i-hour post-heating to <B> 1950 </B> C, water is added,
acidified and unchanged m-chlorophenol removed by means of steam. The 5.5'-diclilot-diphenyl ether-2-carboxylic acid obtained initially is heated to about 95 ° C. for one hour in ten times the amount by weight of concentrated sulfuric acid. This causes ring closure to form 3.6-dicblorxanthone, which is kept by pouring out onto ice and can be purified by recrystallization from alcohol or methanol.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE210599X | 1937-11-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210599A true CH210599A (en) | 1940-07-31 |
Family
ID=5798200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210599D CH210599A (en) | 1937-11-04 | 1938-08-29 | Process for the preparation of an acidic triphenylmethane dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210599A (en) |
-
1938
- 1938-08-29 CH CH210599D patent/CH210599A/en unknown
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