DE240404C - - Google Patents
Info
- Publication number
- DE240404C DE240404C DENDAT240404D DE240404DA DE240404C DE 240404 C DE240404 C DE 240404C DE NDAT240404 D DENDAT240404 D DE NDAT240404D DE 240404D A DE240404D A DE 240404DA DE 240404 C DE240404 C DE 240404C
- Authority
- DE
- Germany
- Prior art keywords
- dichloro
- color
- dyes
- blue
- dye
- 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
- 239000000975 dye Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- XQHYECQMLZJNSI-UHFFFAOYSA-N 2-amino-3,4-diethylbenzaldehyde Chemical compound CCC1=CC=C(C=O)C(N)=C1CC XQHYECQMLZJNSI-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000004961 triphenylmethanes Chemical class 0.000 claims description 2
- VAYOSLLFUXYJDT-RDTXWAMCSA-N LSD Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 claims 1
- 239000000980 acid dye Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 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
- 210000002268 Wool Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DGPBVJWCIDNDPN-UHFFFAOYSA-N 2-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=CC=C1C=O DGPBVJWCIDNDPN-UHFFFAOYSA-N 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
- 238000010792 warming 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAiSE-RfICHESKAiSE-RfICHES
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Jtt 240404 KLASSE 22b. GRUPPE- Jtt 240404 CLASS 22b. GROUP
in BASELin Basel
Zusatz zum Patente 189938 vom 29. September 1906.*)Addition to patent 189938 from September 29, 1906. *)
Patentiert im Deutschen Reiche vom 3. März 1911 ab. Längste Dauer: 28. September 1921. Patented in the German Empire on March 3 , 1911. Longest duration: September 28, 1921.
In der Patentschrift 198729, Zusatz zu 189938, ist gezeigt worden, daß sich aus o-Chlor-p-dialkylaminobenzaldehyden und aromatischen o-Oxycarbonsäuren blauviolette Chromierfarbstoffe der Triphenylmethanreihe darstellen lassen.In the patent specification 198729, addition to 189938, it has been shown that from o-chloro-p-dialkylaminobenzaldehydes and aromatic o-Oxycarboxylic acids represent blue-violet chromating dyes of the triphenylmethane series permit.
Es wurde nun gefunden, daß man einen noch brillanteren Effekt in der Nuance erzielt, wenn man an Stelle der nur in einer Orthostelle durch Chlor substituierten p-Dialkylaminobenzaldehyde die diorthosubstituierten Dichlor-p-dialkylaminobenzaldehyde verwendet. Während die Farbstoffe aus den o-Chlor-p-dialkylaminobenzaldehyden die Wolle nachchromiert lebhaft blauviolett färben, geht durch den Eintritt des zweiten orthoständigen Chloratoms der Ton dieser Färbung in ein prachtvolles, reines Blau über, wobei zugleich auch die Lichtechtheit sich noch erhöht.It has now been found that an even more brilliant effect is achieved in the shade if you replace the p-dialkylaminobenzaldehydes, which are only substituted in one ortho position by chlorine the diortho-substituted dichloro-p-dialkylaminobenzaldehydes are used. While the dyes from the o-chloro-p-dialkylaminobenzaldehydes are wool after chromed color vivid blue-violet, goes through the entry of the second ortho-standing Chloratoms the tone of this coloration in a magnificent, pure blue over, at the same time the lightfastness is also increased.
10,9 kg 2 · ö-Dichlor-^dimethylaminobenzaldehyd werden in 100 kg konzentrierter Schwefelsäure gelöst, mit 15,2 kg o-Kresotinsäure10.9 kg of 2 · δ-dichloro- ^ dimethylaminobenzaldehyde are dissolved in 100 kg of concentrated sulfuric acid with 15.2 kg of o-cresotinic acid
(0H:CHs:C00H = t:2-.6)
versetzt und unter Rühren bei gewöhnlicher Temperatur in 3 bis 4 Stunden zur Leukotriphenylmethanverbindung
kondensiert. Diese wird durch allmählichen Zusatz einer Lösung von 3,5 kg Natriumnitrit in 25 kg konzentrierter
Schwefelsäure und langsames Aufwärmen auf 60 ° zum Farbstoff oxydiert. Die tiefrote Lösung wird nach Erkalten in 1000 1
Wasser gegossen, wobei sich der Farbstoff vollständig ausscheidet; dieser wird abfiltriert,
gewaschen, in wässerigem Ammoniak gelöst und zur Trockne eingedampft. Die freie Farbstoffsäure
bildet ein in Wasser unlösliches, rötlichschwarzes Pulver, das sich in Alkohol mit kirschroter, in konzentrierter Schwefelsäure
mit leuchtend bläulichroter Farbe löst. Ammoniak löst es mit trüb rotbrauner, Natronlauge
mit lebhaft rötlichblauer Farbe. Aus saurem Bade zieht der Farbstoff auf Wolle in bordeauxroten Tönen, die beim
Nachchromieren in ein brillantes, intensives Blau von sehr guter Alkali-, Walk- und Pottingechtheit
übergehen. Auch beim Drucken auf Baumwolle erzeugt er die nämliche Nuance. (0H: CH s : C00H = t: 2-.6)
added and condensed with stirring at ordinary temperature in 3 to 4 hours to the leukotriphenylmethane compound. This is oxidized to the dye by gradually adding a solution of 3.5 kg of sodium nitrite in 25 kg of concentrated sulfuric acid and slowly warming it to 60 °. After cooling, the deep red solution is poured into 1000 l of water, the dye separating out completely; this is filtered off, washed, dissolved in aqueous ammonia and evaporated to dryness. The free dye acid forms a reddish black powder which is insoluble in water and which dissolves in alcohol with a cherry-red color and in concentrated sulfuric acid with a bright bluish-red color. Ammonia dissolves it with a cloudy red-brown color, and sodium hydroxide solution with a vivid reddish-blue color. From an acid bath, the dye pulls onto wool in burgundy-red tones, which, when chromium-plated, turn into a brilliant, intense blue with very good alkali, milled and potting fastness. It also produces the same shade when printing on cotton.
Einen analogen Farbstoff mit noch etwas blauerer Nuance der chromierten Färbung erhält man aus 2 · o-Dichlor-^diäthylaminobenzaldehyd. An analogous dye with a slightly bluer shade of the chromed color is obtained from 2 · o-dichloro ^ diethylaminobenzaldehyde.
■ *) Frühere Zusatzpatente: 198729, 198909, 199943, 199944, 209535, 213502 und 213503.■ *) Previous additional patents: 198729, 198909, 199943, 199944, 209535, 213502 and 213503.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE240404C true DE240404C (en) |
Family
ID=499768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT240404D Active DE240404C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE240404C (en) |
-
0
- DE DENDAT240404D patent/DE240404C/de active Active
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