DE183331C - - Google Patents
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- Publication number
- DE183331C DE183331C DENDAT183331D DE183331DA DE183331C DE 183331 C DE183331 C DE 183331C DE NDAT183331 D DENDAT183331 D DE NDAT183331D DE 183331D A DE183331D A DE 183331DA DE 183331 C DE183331 C DE 183331C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- red
- violet
- dark
- black
- 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.)
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- 239000000975 dye Substances 0.000 claims description 10
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-Aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 238000001556 precipitation Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 229940018563 3-aminophenol Drugs 0.000 description 5
- NIKFYOSELWJIOF-UHFFFAOYSA-O Fuchsine Chemical compound Cl.C1=C(N)C(C)=CC(C(=C2C=CC(=[NH2+])C=C2)C=2C=CC(N)=CC=2)=C1 NIKFYOSELWJIOF-UHFFFAOYSA-O 0.000 description 4
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- 241000872198 Serjania polyphylla Species 0.000 description 3
- 125000000853 cresyl group Chemical class C1(=CC=C(C=C1)C)* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 240000000358 Viola adunca Species 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
- 150000007513 acids Chemical class 0.000 description 2
- 239000011449 brick Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SOAAGHDAWFEEPP-JZJYNLBNSA-N (4Z)-4-[(2,4-dimethylphenyl)hydrazinylidene]-3-oxonaphthalene-2,7-disulfonic acid Chemical compound CC1=CC(C)=CC=C1N\N=C/1C2=CC=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C\1=O SOAAGHDAWFEEPP-JZJYNLBNSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- OXOBKZZXZVFOBB-UHFFFAOYSA-N 2-Diphenylmethylpyrrolidine Chemical compound C1CCNC1C(C=1C=CC=CC=1)C1=CC=CC=C1 OXOBKZZXZVFOBB-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229940069002 Potassium Dichromate Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- JNIGYQOBELCEIZ-MAKDUZDQSA-L barium(2+);5-chloro-4-methyl-2-[(2Z)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]benzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N\N=C/2C3=CC=CC=C3C=CC\2=O)=C1S([O-])(=O)=O JNIGYQOBELCEIZ-MAKDUZDQSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- -1 diazo sulfonic acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22«. GRUPPECLASS 22 «. GROUP
in BASEL.in Basel.
Verfahren zur Darstellung von o-Oxymonoazofarbstoffen.Process for the preparation of o-oxymonoazo dyes.
Zusatz zum Patente 181326 vom 10. Mai 1904.Addendum to patent 181326 of May 10, 1904.
Patentiert im Deutschen Reiche vom 1. Juli 1904 ab. Längste Dauer: 9. Mai 1919.Patented in the German Empire on July 1, 1904. Longest duration: May 9, 1919.
In der Patentschrift 181326 wird ein Verfahren zur Darstellung chromierbarer o-Oxyazofarbstoffe beschrieben, welches darin besteht, daß man die nach Patent 171024 erhältlichen i-Diazo-2-naphtolsulfosäureh bezw. Sulfosäuren des Naphtalin-i-2-diazooxydes mit Naphtolen, deren Monosulfo- und -carbonsäuren, Aminonaphtolen und deren Sulfosäuren, Dioxynaphtalinen und deren SuIfο ίο säuren und Resorcin kombiniert. Wie weitere Untersuchungen nun ergeben haben, sind außer den genannten Körperklassen auch die m-Aminophenole und m-Diamine fähig, sich mit großer Leichtigkeit mit den erwähnten Diazoverbindungen zu vereinigen unter Bildung von technisch ebenfalls sehr wertvollen Farbstoffen. Die Kupplung der Diazösulfosäuren mit den Diaminen tritt in vorliegenden Fällen besonders leicht in essigsaurer oder doch neutraler Lösung ein, mit den Aminophenolen jedoch am zweckmäßigsten in Gegenwart von Ätzkalk.Patent 181326 describes a process for the preparation of chromable o-oxyazo dyes, which consists in that the i-diazo-2-naphtolsulfosäureh obtainable according to patent 171024 bezw. Sulphonic acids of naphthalene-i-2-diazooxide combined with naphthols, their monosulpho- and carboxylic acids, aminonaphthols and their sulphonic acids, dioxynaphthalenes and their sulfo acids and resorcinol. As further investigations have now shown, in addition to the body classes mentioned, the m-aminophenols and m-diamines are also able to combine with great ease with the diazo compounds mentioned to form technically also very valuable dyes. The coupling of the diazo sulfonic acids with the diamines occurs particularly easily in the present cases in acetic acid or at least neutral solution, but with the aminophenols it is most expedient in the presence of quicklime.
Die so erhältlichen Farbstoffe färben Wolle aus essigsaurem Bade in ziegelroten bis dunkelbraunvioletten Tönen, welche durch darauffolgende Behandlung mit Kaliumbichromat in violett- bis grünlichschwarze, mit Kupfersulfat in bräunlich- bis schwarzviolette Nuancen von sehr guter Licht- und bezüglich der chromierten Färbungen zum Teil ausgezeichneter Walk- und Pottingechtheit übergehen.The dyes obtainable in this way dye wool from an acetic acid bath in brick red to dark brown purple Tones, which by subsequent treatment with potassium dichromate in violet to greenish black, with copper sulfate in brownish to black-violet nuances of very good light and chrome Dyeings, some of which have excellent mill and potting fastness, pass over.
1. 300 1 einer Lösung, enthaltend 14,5 kg salzsaures m-Aminophenol werden unter Rühren mit 40 kg 25 prozentiger Kalkmilch versetzt, worauf man 30 kg Bariumsalz der I-Diazo-2-naphtol-6-sulfosäure einträgt. Nach beendeter Kombination wird mit Wasser verdünnt, aufgekocht und die tief rote Lösung filtriert. Nach Zusatz von Salzsäure zum Fiitrat wird der als dunkelrotbrauner Niederschlag ausfallende Farbstoff abfiltriert, ausgewaschen, hierauf in Ammoniak gelöst und zur Trockne verdampft.1. 300 l of a solution containing 14.5 kg Hydrochloric acid m-aminophenol is mixed with 40 kg of 25 percent milk of lime while stirring, whereupon 30 kg of barium salt of I-diazo-2-naphthol-6-sulfonic acid enters. When the combination is complete, it is diluted with water, boiled and the deep red solution filtered. After the addition of hydrochloric acid to the filtrate, it becomes a dark red-brown precipitate precipitated dye filtered off, washed out, then dissolved in ammonia and evaporated to dryness.
2. 12 kg m-Toluylendiamin und 36 kg saures Natriumsalz der i-Diazo-2-riaphtol-4-6-disulfosäure werden zusammen unter Rühren und Zusatz von 5 kg 40 prozentiger Essigsäure in 50 1 Wasser gelöst. Die Kombination ist bei einer Temperatur von 25 ° C. in einigen Stunden beendigt, worauf man die dunkelbraune, schwach metallisch grünglänzende Lösung mit Salzsäure ansäuert und mit Kochsalzlösung versetzt. Der als rotbrauner Niederschlag ausfallende Farbstoff wird abfiltriert, gepreßt und getrocknet.2. 12 kg of m-tolylenediamine and 36 kg acid sodium salt of i-diazo-2-riaphthol-4-6-disulfonic acid are together with stirring and the addition of 5 kg of 40 percent acetic acid dissolved in 50 l of water. The combination is completed in a few hours at a temperature of 25 ° C, whereupon the dark brown, slightly metallic green-glossy solution acidified with hydrochloric acid and with Saline solution added. The dye which separates out as a red-brown precipitate is filtered off, pressed and dried.
Von den nach vorstehendem Verfahren erhältlichen Farbstoffen sind eine Anzahl mit ihren Eigenschaften und den Nuancen ihrer direkten nachchromierten und gekupferten Färbungen in umstehender Tabelle zusammengestellt. Of the dyes obtainable by the above process, a number are with their properties and the nuances of their direct chrome-plated and copper-plated The colors are compiled in the table below.
ausDiazo compound
the end
mitCoupled
with
des
trockenen
FarbstoffesAppearance
of
dry
Dye
in
WasserFarl
in
water
auf Zusatz
Salzsäureae of his loos
on addition
hydrochloric acid
von
■ Ammoniakung
from
■ ammonia
in konzen
trierter
Schwefel
säuresolution
in conc
trotter
sulfur
acid
aus
essigsaurem
Badenuance
the end
acetic acid
Bath
hach-
chromiertthe coloring
really
chromed
nach-
gekupferton wool
after-
coppered
4-sulfosäureι-amino-2-naphthol-
4-sulfonic acid
phenolm-amino
phenol
glänzendes. Pulverbrownish green
shiny. powder
Niederschlagbrown
Precipitation
Violettstichblack with
Violet cast
kresolm-amino
cresol
Niederschlagbrownish red
Precipitation
Violettstichblack with
Violet cast
violettblack
violet
diaminm-phenylene
diamine
Pulverdark brown
powder
Niederschlagreddish brown
Precipitation
schwarzbrownish
black
braunviolettdark
brown purple
diaminm-toluylene
diamine
Pulverblackish green
powder
Niederschlagyellowish brown
Precipitation
schwarzgreenish
black
braunviolettdark
brown purple
6-sulfosäurei-amino-2-naphthol-
6-sulfonic acid
phenolm-amino
phenol
glänzendes Pulvergreenish black
shiny powder
Niederschlagblack-brown
Precipitation
Violettstichblack with
Violet cast
kresolm-amino
cresol
glänzendes Pulvergreenish black
shiny powder
Niederschlagreddish brown
Precipitation
violettblaudark-
violet blue
schwarzviolet
black
3-6-disulfosäureι -Amino-2-naphtol-
3-6-disulfonic acid
phenolm-amino
phenol
Pulvergreenish black
powder
mit braunem
Niederschlagred solution
with brown
Precipitation
violettbrownish
violet
kresolm-amino
cresol
glänzendes Pulvergreenish black
shiny powder
Niederschlagbrownish red
Precipitation
braunviolettdark
brown purple
blaugraudark
blue-gray
diaminm-phenylene
diamine
Pulvergreenish black
powder
Niederschlagbrown
Precipitation
4-6-disulfosäure'i-amino-2-naphthol-
4-6-disulfonic acid
phenolm-amino
phenol
Pulverdark green brown
powder
diaminm-phenylene
diamine
Niederschlagyellowish brown
Precipitation
diaminm-toluylene
diamine
Niederschlagreddish yellow
Precipitation
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE183331C true DE183331C (en) |
Family
ID=447342
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT183331D Active DE183331C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE183331C (en) |
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