DE213502C - - Google Patents
Info
- Publication number
- DE213502C DE213502C DENDAT213502D DE213502DA DE213502C DE 213502 C DE213502 C DE 213502C DE NDAT213502 D DENDAT213502 D DE NDAT213502D DE 213502D A DE213502D A DE 213502DA DE 213502 C DE213502 C DE 213502C
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- aminobenzaldehyde
- dibromo
- dyes
- blue
- 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.)
- Active
Links
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 150000003935 benzaldehydes Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 2
- QPFCKZZGXGQOJQ-UHFFFAOYSA-N BrC1(C(C=O)C=CC=C1)Cl Chemical compound BrC1(C(C=O)C=CC=C1)Cl QPFCKZZGXGQOJQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000980 acid dye Substances 0.000 claims 1
- -1 dibromo-2-chloro-5-aminobenzaldehyde Chemical compound 0.000 claims 1
- 150000004961 triphenylmethanes Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical class NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 240000000358 Viola adunca Species 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VFMNMBPTALFANA-UHFFFAOYSA-N 5-amino-2-chlorobenzaldehyde Chemical compound NC1=CC=C(Cl)C(C=O)=C1 VFMNMBPTALFANA-UHFFFAOYSA-N 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- FZDTWFNKSDSLRY-UHFFFAOYSA-N ClC1(C(C=CC=C1)C)Br Chemical compound ClC1(C(C=CC=C1)C)Br FZDTWFNKSDSLRY-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
-
- 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
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/22—Amino derivatives of triarylmethanes containing OH groups bound to an aryl nucleus and their ethers and esters
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-■Λ* 213502 -/ KLASSE 22 b. GRUPPE- ■ Λ * 213502 - / CLASS 22 b. GROUP
in BASEL.in Basel.
Zusatz zum Patente 189938 vom 29. September 1906.Addendum to patent 189938 from September 29, 1906.
Patentiert im Deutschen Reiche vom 19. Juli 1908 ab. Längste Dauer: 28.September 1921.Patented in the German Empire on July 19, 1908. Longest duration: September 28, 1921.
In der Patentschrift 199943 (Zusatz zum Patent 189938) sind beizenfärbende Triphenylmethanfarbstoffe aus diorthosubstituierten Benzaldehyden beschrieben, die wegen ihrer besonderen Schönheit und Echtheit bemerkenswert sind. Die vorliegende Erfindung erweitert die Zahl der aus diorthohalogenierten Benzaldehyden dargestellten Farbstoffe durch die Verwendung einiger neuer o-o-Dihalogenbenzaldehyde, die in der Mehrzahl dadurch ausgezeichnet sind, daß sie in beiden Orthostellungen verschiedene Halogene, nämlich Chlor und Brom, enthalten.In patent specification 199943 (addition to Patent 189938) are stain-coloring triphenylmethane dyes described from diorthosubstituted benzaldehydes, which are remarkable for their particular beauty and authenticity are. The present invention expands the number of dyes made from diorthohalogenated benzaldehydes the use of some new o-o-dihalobenzaldehydes, the majority of which thereby are excellent that they have different halogens in both ortho positions, namely Chlorine and bromine.
Von den in der Patentschrift 199943 beschriebenen Farbstoffen unterscheiden sich die
nach vorliegendem Verfahren erhaltenen dadurch, daß die chromierten Färbungen der
letzteren eine viel grünere Nuance zeigen.
Was im besonderen die trihalogenierten m-Aminobenzaldehyde betrifft, so war es nicht
vorauszusehen, ob sich' solche Derivate mit freien Aminogruppen zur Oxydation mittels
Nitrosylschwefelsäure eignen würden, da die letztere die Aminogruppen leicht angreift.The dyes obtained by the present process differ from the dyes described in patent specification 199943 in that the chromed colorations of the latter show a much greener shade.
As regards the trihalogenated m-aminobenzaldehydes in particular, it could not be foreseen whether such derivatives with free amino groups would be suitable for oxidation by means of nitrosylsulfuric acid, since the latter easily attacks the amino groups.
Dies ist offenbar der Fall, denn es ist zur Erzielung intensiver Farbstoffe vorteilhaft, die Menge des Oxydationsmittels zu vergrößern, z. B. zu verdoppeln. Die alsdann erzeugten chromierten Färbungen sind von etwas trüberem Tone und zeigen den Vorteil, gut zu 35 This is apparently the case, because it is advantageous to achieve intense dyes to increase the amount of oxidizing agent, e.g. B. to double. The chromed colorations then produced are of a somewhat more cloudy shade and show the advantage of being good at 35
decken. Die in Betracht kommenden neuen Aldehyde sind:cover. The new aldehydes to be considered are:
o-Chlor-o-brombenzaldehyd, dargestellt aus o-Chlor-o-bromtoluol nach bekannten Methoden, kristallisiert aus Alkohol in farblosen Spießen vom Schmelzpunkt 68°.o-chloro-o-bromobenzaldehyde, shown from o-chloro-o-bromotoluene according to known methods, crystallizes from alcohol in colorless skewers with a melting point of 68 °.
4 · 6 - Dibrom - 2 - chlor - 5 - aminobenzaldehyd, durch Bromieren des 2-Chlor-5-aminobenzaldehyds -in wäßriger Suspension erhalten, fällt aus der Benzollösung als kristallinisches, korkfarbiges Pulver aus, Schmelzpunkt 124 °.4 · 6 - dibromo - 2 - chloro - 5 - aminobenzaldehyde, by bromination of 2-chloro-5-aminobenzaldehyde - Obtained in aqueous suspension, falls from the benzene solution as a crystalline, cork-colored Powder off, melting point 124 °.
2 · 4 · 6 -Tribrom-s-aminobenzaldehyd-, dargestellt durch Bromieren des m-Aminobenzaldehyds, korkfarbiges kristallinisches Pulver aus Benzol, Schmelzpunkt 136 bis 137°.2x4x6 -tribromo-s-aminobenzaldehyde- by brominating m-aminobenzaldehyde, cork-colored crystalline powder from benzene, melting point 136 to 137 °.
4"6-Dibrom-2-chlor-5-oxybenzaldehyd, durch Bromieren des 2-Chlor-5-oxybenzaldehyds in wäßriger Lösung erhalten, kristallisiert aus Alkohol in schwach gelblich braunen Nadeln vom Schmelzpunkt ii6°. Das Verfahren ist das gleiche wie im Patent 199943.4 "6-Dibromo-2-chloro-5-oxybenzaldehyde, by brominating the 2-chloro-5-oxybenzaldehyde in obtained aqueous solution, crystallized from alcohol in pale yellowish brown needles with a melting point of ii6 °. The procedure is the same as in the 199943 patent.
15,7 kg 4 · 6 - Dibrom - 2 - chlor - 5 - aminobenzaldehyd und 15,2 kg ο - Kresotinsäure werden mit 100 kg konzentrierter Schwefelsäure bei gewöhnlicher Temperatur gerührt, bis der Aldehyd verschwunden ist, dann wird durch allmählichen Zusatz einer Lösung von 7 kg Natriumnitrit in 25 kg konzentrierter Schwefel-15.7 kg 4 x 6 - dibromo - 2 - chloro - 5 - aminobenzaldehyde and 15.2 kg of ο - cresotinic acid are combined with 100 kg of concentrated sulfuric acid ordinary temperature stirred until the aldehyde has disappeared, then is through gradual addition of a solution of 7 kg of sodium nitrite in 25 kg of concentrated sulfur
säure zum Farbstoff oxydiert, wobei sich die Schmelze tief rot färbt. Nach mehrstündigem Erwärmen bei ..Wasserbadtemperatur und darauffolgendem Erkalten wird das Produkt in iooo 1 Wasser gegossen. Der Farbstoff scheidet sich als roter Niederschlag vollständig aus, er wird filtriert, gewaschen und getrocknet. Das bläulich rote Pulver ist unlöslich in Wasser, löslich in Soda mit ganzacid oxidizes to the dye, whereby the melt turns deep red. After several hours The product is heated to ... water bath temperature and then cooled Poured in 10000 water. The dye separates out completely as a red precipitate off, it is filtered, washed and dried. The bluish red powder is insoluble in water, soluble in soda with whole
ίο schwach braunvioletter Farbe; 2oprozentiges Ammoniak löst es mit braunroter Farbe, die beim. Verdünnen mit Wasser unter teilweiser •Abscheidung violetter Flocken in Blauyiolett übergeht. Natronlauge löst mit intensiv blauvioletter, Alkohol mit lebhaft orangeroter, konzentrierte Schwefelsäure mit lebhaft blauroter Farbe. Der Farbstoff färbt Wolle in saurem Bad bläulichrot, nachchromiert alkali echt blau. Ebenso wird Baumwolle im Druck mit Chrombeizen gefärbt. Die Farbstoffe aus den anderen Aldehyden zeigen ähnliche Reaktionen und Färbeeigenschaften.ίο pale brown-purple color; 2 percent Ammonia dissolves it with a brownish-red color, which when. Dilute with water under partial • Separation of violet flakes turns into blue-violet. Caustic soda dissolves with an intense blue-violet, Alcohol with bright orange-red, concentrated sulfuric acid with a bright blue-red color. The dye dyes wool in acidic bath bluish-red, after-chromed alkali real blue. Likewise, cotton is used in printing colored with chrome stains. The dyes from the other aldehydes show similar reactions and coloring properties.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE213502C true DE213502C (en) |
Family
ID=475143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT213502D Active DE213502C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE213502C (en) |
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0
- DE DENDAT213502D patent/DE213502C/de active Active
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