DE234026C - - Google Patents
Info
- Publication number
- DE234026C DE234026C DENDAT234026D DE234026DA DE234026C DE 234026 C DE234026 C DE 234026C DE NDAT234026 D DENDAT234026 D DE NDAT234026D DE 234026D A DE234026D A DE 234026DA DE 234026 C DE234026 C DE 234026C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- violet
- acids
- oxidized
- condensed
- 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
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000001003 triarylmethane dye Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- NJAPCAIWQRPQPY-UHFFFAOYSA-N benzyl hydrogen carbonate Chemical class OC(=O)OCC1=CC=CC=C1 NJAPCAIWQRPQPY-UHFFFAOYSA-N 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000975 dye Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JZIWAPPDDUCELD-UHFFFAOYSA-N ClC1=C(C=CC=C1)CCC1=C(C(C(=O)O)=CC=C1)O Chemical compound ClC1=C(C=CC=C1)CCC1=C(C(C(=O)O)=CC=C1)O JZIWAPPDDUCELD-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 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
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N Diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N Nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 206010039587 Scarlet fever Diseases 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
- 229940054021 anxiolytics Diphenylmethane derivatives Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 125000006840 diphenylmethane group Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- -1 o-chlorobenzyl-p-cresotinic acid Chemical compound 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 234026 KLASSE 225. GRUPPE- M 234026 CLASS 225. GROUP
Patentiert im Deutschen Reiche vom 26. Januar 1910 ab.Patented in the German Empire on January 26, 1910.
Die zur Darstellung nachchromierbarer Triarylmethanfarbstoffe benutzten Diphenylmethanderivate sind ausschließlich symmetrische Körper, die z. B. durch Kondensation von Formaldehyd mit zwei Molekülen eines Phenols oder einer Phenolcarbonsäure (s. Patentschrift 49970 und Berichte 25, S. 939 und 2671) erhalten werden.The diphenylmethane derivatives used for the preparation of triarylmethane dyes that can be re-chromated are exclusively symmetrical bodies, z. B. by condensation of formaldehyde with two molecules of a phenol or a phenol carboxylic acid (see Patent Specification 49970 and Reports 25, pp. 939 and 2671) will.
Es wurde nun gefunden, daß sich auch unsymmetrische Diarylmethane, deren Methylengruppe zwei verschiedene Reste verkettet, zu Hydrolen oxydieren lassen, und daß diese durch Kondensation mit einem Molekül eines Phenols bei Gegenwart von Oxydationsmitteln wertvolle nachchromierbare Farbstoffe liefern. Diese unterscheiden sich in ihren Eigenschaften erheblich von den bisher aus Diphenylmethanen dargestellten nachchromierbaren Triphenylmethanfarbstoffen, wie z. B. durch ihre blaueren Nuancen und ihr besseres Egalisierungsvermögen. It has now been found that unsymmetrical diarylmethanes, their methylene group two different residues are linked, can be oxidized to hydroles, and that these are formed by condensation with a molecule of one Phenols provide valuable re-chromable dyes in the presence of oxidizing agents. These differ considerably in their properties from those previously made from diphenylmethanes represented post-chromable triphenylmethane dyes, such as. B. by their bluer nuances and their better leveling ability.
9,2 Teile o-Chlorbenzyl-o-kresotinsäure (erhalten aus o-Chlorbenzylalkohol und o-Kresotinsäure) und 6 Teile o-Kresotinsäure werden mit 160 Teilen starker Schwefelsäure und der nötigen Menge Nitrosylschwefelsäure so lange bei mittlerer Temperatur gerührt, bis die Menge des Farbstoffs - nicht mehr zunimmt. Die Schmelze wird auf Eis gegossen und der Farbstoff abfiltriert. Derselbe bildet ein rotorangefarbenes Pulver, das in Wasser kaum, in Natronlauge violett löslich ist. Wolle wird nach dem Chromieren blau gefärbt.9.2 parts of o-chlorobenzyl-o-cresotinic acid (obtained from o-chlorobenzyl alcohol and o-cresotinic acid) and 6 parts of o-cresotinic acid with 160 parts of strong sulfuric acid and the necessary amount of nitrosylsulfuric acid stirred at medium temperature until the Amount of dye - no longer increases. The melt is poured onto ice and the Dye filtered off. It forms a red-orange powder, which in water hardly is violet soluble in sodium hydroxide solution. After chroming, wool is dyed blue.
Als Oxydationsmittel können auch Salpetersäure, Nitrokörper, konzentrierte Schwefelsäure, Oleum verwandt werden.Nitric acid, nitro bodies, concentrated sulfuric acid, Oleum can be used.
Die Darstellung der Methane und die Farbstoffbildung kann in einer Operation ausgeführt werden. Andererseits können auch die Methane zuerst zu Hydrolen oxydiert und diese mit den Phenolen kondensiert und die Leukosäure zum Farbstoff oxydiert werden. The preparation of the methane and the formation of the dye can be carried out in one operation will. On the other hand, the methanes can first be oxidized to hydroles and this condenses with the phenols and the leuco acid is oxidized to the dye.
Die Farbstoffe können auch auf chromierter Wolle oder direkt mit Bichromat gefärbt werden.The dyes can also be dyed on chromed wool or directly with bichromate will.
In der folgenden Tabelle sind die Eigenschaften einiger nach vorliegendem Verfahren erhältlichen Farbstoffe charakterisiert.The following table lists the properties of some of the methods used here available dyes characterized.
30 dye
30th
in Wassersolubility
in water
in Natronlaugesolution
in caustic soda
WollfärbungChromed
Wool dye
+ i-Naphtol-2-carbonsäure-7-sulfosäure2-oxy-3-carboxybenzyl-o-cresotinic acid
+ i-naphthol-2-carboxylic acid-7-sulfonic acid
35 4- 2-Naphtol-3 · 6-disulfosäure2-oxy-3-carboxybenzyl-o-cresotinic acid
35 4- 2-naphthol-3 x 6-disulfonic acid
in Wassersolubility
in water
in Natronlaugesolution
in caustic soda
WollfärbungChromed
Wool dye
+ o-Kresotinsäure 5 z-Oxy-s-carboxybenzyl diethylaniline
+ o-cresotinic acid
+ Salicylsäureo-chlorobenzyl-p-cresotinic acid
+ Salicylic acid
o-Chlorbenzyl-o-kresotinsäure
+ o-KresotinsäureIO
o-chlorobenzyl-o-cresotinic acid
+ o-cresotinic acid
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE234026C true DE234026C (en) |
Family
ID=493918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT234026D Active DE234026C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE234026C (en) |
-
0
- DE DENDAT234026D patent/DE234026C/de active Active
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