DE135016C - - Google Patents
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- Publication number
- DE135016C DE135016C DENDAT135016D DE135016DA DE135016C DE 135016 C DE135016 C DE 135016C DE NDAT135016 D DENDAT135016 D DE NDAT135016D DE 135016D A DE135016D A DE 135016DA DE 135016 C DE135016 C DE 135016C
- Authority
- DE
- Germany
- Prior art keywords
- toluene
- nitro
- dye
- sulfamidotoluene
- wool
- 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 17
- 150000008049 diazo compounds Chemical class 0.000 claims description 8
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- OXNIZHLAWKMVMX-UHFFFAOYSA-N Picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 9
- 210000002268 Wool Anatomy 0.000 description 9
- 229940114148 picric acid Drugs 0.000 description 9
- 229950002929 trinitrophenol Drugs 0.000 description 9
- 238000002844 melting Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-Toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- PZKPUGIOJKNRQZ-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,3-diamine Chemical class CC1(N)CC(N)=CC=C1 PZKPUGIOJKNRQZ-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N Benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N Picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- -1 p-toluenesulfonyl Chemical group 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
-[ES-[IT
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, dafs man beizenfärbende Azofarbstoffe für Wolle von grofser Echtheit erhält, wenn man die Diazoverbindungen von Nitroderivaten des o-Amidophenols mit m-Amido-arylsulfamiden combinirt, in denen die ParaStellung zu der Arylsulfamidgruppe besetzt ist, und welchen demnach die folgende Constitutionsformel zukommt:It has been found that stain-dyeing azo dyes are very fast for wool obtained when the diazo compounds of nitro derivatives of o-amidophenol with m-amido-arylsulfamides combined, in which the para position to the arylsulfamide group is occupied is, and which accordingly has the following constitutional formula:
XX
11
NHNH
NH- S0.2 — Aryl. NH- S0. 2 - aryl.
Die auf diesem Wege erhaltenen Farbstoffe erzeugen auf Wolle unter Anwendung von Chrombeizen Nuancen, welche je nach Wahl der Componenten zwischen einem gelblichen Roth und einem violetten Bordeaux schwanken.The dyes obtained in this way produce on wool using Chrome stain nuances which, depending on the choice of components, can be yellowish Roth and a purple Bordeaux fluctuate.
Die Darstellung der als Ausgangsmaterial dienenden m- Amido - ärylsulfamide soll das folgende Beispiel erläutern:The representation of the m-amido-arylsulfamides used as the starting material is intended to do so explain the following example:
15,2 Theile o-Nitro-p-toluidin werden in Wasser suspendirt; zu der auf dem Wasserbade erwärmten Lösung giebt man unter starkem Umrühren 20 Theile p-Toluolsulfochlorid zu und trägt, um die Reaction zu vervollständigen, nach einiger Zeit nach und nach 6 Theile Soda ein. Das Reactionsprodukt ist zum gröfsten Theile ausgeschieden und kann durch Lösen in verdünnter Natronlauge und Fällen mit Salzsäure gereinigt werden. Es zeigt den Schmelzpunkt 1640. Durch reducirende Mittel, wie ζ B. Zinkstaub und Salzsäure bezw.. Essigsäure, wird dieser Körper in das Amidosulfamid folgender Constitution übergeführt:15.2 parts of o-nitro-p-toluidine are suspended in water; 20 parts of p-toluenesulphonyl chloride are added to the solution warmed on the water bath, with vigorous stirring, and, after a while, 6 parts of soda are gradually added to complete the reaction. Most of the reaction product has been separated out and can be purified by dissolving it in dilute sodium hydroxide solution and precipitating it with hydrochloric acid. It shows the melting point 164 0 . By reducing agents such as zinc dust and hydrochloric acid or acetic acid, this body is converted into the amidosulfamide of the following constitution:
'3'3
/NEL/ NEL
NH- SO2-C1 H1.NH-SO 2 -C 1 H 1 .
Dasselbe ist sowohl in verdünnter Natronlauge, wie in Mineralsäuren löslich, kann aber aus diesen Lösungen durch Zusatz von Essigsäure bezw. Natriumacetat gefällt werden. Es stellt ein weifses krystallinisches Pulver vor, das bei i6o° schmilzt.It is soluble in dilute caustic soda as well as in mineral acids, but it can be derived from it these solutions BEZW by adding acetic acid. Sodium acetate can be precipitated. It puts a white crystalline powder which melts at 160 °.
Geht man bei der Darstellung der Amidoarylsulfamide von einem unsymmetrisch substituirten m-Diamin aus, so kommt selbstverständlich die nachfolgende Reduction der Nitrogruppe in Wegfall. So entsteht beim Behandeln des o-Dimethylamido-p-amidotoluols in wässeriger Suspension auf dem Wasserbade mit 2-Chlor-5-Nitrobenzolsulfochlorid (Beilstein, III. Aufl. II, S. 127) direct das Sulfamid. folgender Constitution:If the representation of the amidoarylsulfamides is based on an unsymmetrically substituted one m-diamine, then of course the subsequent reduction of the nitro group occurs in omission. This is how the o-dimethylamido-p-amidotoluene is produced in aqueous suspension on the water bath with 2-chloro-5-nitrobenzenesulfochloride (Beilstein, III. Ed. II, p. 127) directly the sulfamide. of the following constitution:
CH3 CH 3
' /N(CH3J2 ' / N (CH 3 J 2
/
NH-SO2-(^) /
NH-SO 2 - (^)
/ Cl./ Cl.
Dasselbe löst sich leicht in Soda und schmilzt bei 1440. .The same easily dissolves in soda and melts at 144 0 . .
In analoger Weise erhält man die in nachstehenden Beispielen erwähnten übrigen Amidoarylsulfamide, welche in ihrem allgemeinen Verhalten den eben beschriebenen Körpern gleichen.The other amidoarylsulfamides mentioned in the examples below are obtained in an analogous manner, which in their general behavior resemble the bodies just described.
Nr. I. o-Nitro-p-toluol-p-sulfamidotoluolNo. I. o-nitro-p-toluene-p-sulfamidotoluene
,NO,, NO,
JVH- SO2 -( )>- CH3. JVH- SO 2 - ( )> - CH 3 .
Nr. Ia. o-Amido-p-toluol-p-sulfamidotoluolNo. Ia. o-amido-p-toluene-p-sulfamidotoluene
CH3 CH 3
λ/Ν H2 λ / Ν H 2
NH ■ SO2 -( y~ CH3.NH ■ SO 2 - (y ~ CH 3 .
Nr. II. o-Dimethylamido-p-toluol-p-sulfamidotoluol No. II. O-Dimethylamido-p-toluene-p-sulfamidotoluene
CH3 CH 3
/N(CH3J2 / N (CH 3 J 2
NH. SO2 -( )- CiT3. NH. SO 2 - ( ) - CiT 3 .
Nr. III. Di-ρ-toluol-p-Sulfamido-m-Nitrobenzidin No. III. Di-ρ-toluene-p-sulfamido-m-nitrobenzidine
NO2 NO 2
C1H1. S O2- HN-C 1 H 1 . SO 2 - HN-
-NH-O2S-C7H7.-NH-O 2 SC 7 H 7 .
Nr. Ilia. Di-p-toluol-p-Sulfamido-m-Amidobenzidin No. Ilia. Di-p-toluene-p-sulfamido-m-amidobenzidine
NH2 NH 2
C7H1-SO2-HN-C 7 H 1 -SO 2 -HN-
-NH-O2S-C7H7.-NH-O 2 SC 7 H 7 .
Nr. IV. o-Nitro-p-toluol-p-Sulfamidochlorbenzol No. IV. O-nitro-p-toluene-p-sulfamidochlorobenzene
Cl s/N0.2 Cl s / N0. 2
NH- SO,NH- SO,
>- CH. > - CH.
Nr. IVa. o- Amido- ρ- toluol - p-Sulfamidochlorbenzol No. IVa. o- amido- ρ- toluene - p-sulfamidochlorobenzene
s NHs NH
NH- S0.2-( )- CiT3. NH- S0. 2 - ( ) - CiT 3 .
Nr. V. o-Dimethylamido- ι -Chlor- 5 -Nitrobenzol - ρ - SulfamidotoluolNo. V. o-Dimethylamido- ι -Chlor- 5 -nitrobenzene - ρ - sulfamidotoluene
CiY3 CiY 3
Ix /N (CH3J2 I x / N (CH 3 J 2
Cl
I \ Cl
I \
nh-so2-( ynh-so 2 - (y
\ NO2.\ NO 2 .
Nr. VI. o-Nitro-p-Chlorbenzol-p-Sulfamidotoluol No. VI. o-nitro-p-chlorobenzene-p-sulfamidotoluene
CH3 λ/N O2 CH 3 λ / NO 2
NH-SO2-(~^)-Cl.NH-SO 2 - (~ ^) - Cl.
Nr. Via. ο - Amido-p- Chlorbenzol -p -Sulfamidotoluol No. Via. ο - amido-p-chlorobenzene -p -sulfamidotoluene
CH3 CH 3
Nr. VII. ο-Nitro-Benzol-ρ-SulfamidotoluolNo. VII. Ο-nitro-benzene-ρ-sulfamidotoluene
Nr. Vila. o-Amido-Benzol-p-Sulfamidotoluol CH No. Vila. o-amido-benzene-p-sulfamidotoluene CH
11 /NH2 / NH 2
Farbstoff Pikraminsä'ure-azo-o-Amidop-toluol-ρ-sulfamidotoluol. Colorant picric acid azo-o-amidop-toluene-ρ-sulfamidotoluene.
27,3 kg p-Toluolsulfamido-amidotoluol werden in ca. 500 1 Wasser unter Zusatz von 4 kg Aetznatron gelöst. Zu dieser Lösung werden dann noch 11 kg Soda zugefügt, und man läfst alsdann unter gutem Rühren die aus 21,4 kg Pikraminsäure erhaltene Diazoverbindung langsam einlaufen. Der dabei entstehende Farbstoff scheidet sich aus und wird durch Filtriren von den. Mutterlaugen getrennt. Er färbt Wolle ohne Anwendung von Beizen dunkelroth; beim Nachchromiren oder bei dem27.3 kg of p-toluenesulfamido-amidotoluene will be dissolved in approx. 500 l of water with the addition of 4 kg of caustic soda. Become this solution then another 11 kg of soda are added, and then it is drained out with thorough stirring Slowly run in 21.4 kg of picric acid obtained diazo compound. The resulting The dye separates out and is filtered off from the. Mother liquors separately. He dyes wool dark red without the use of stains; in post-chrome plating or in the
Färben nach der durch D. R. P. 122284 bekannt gewordenen Methode wird die Nuance blaustichiger, und die Färbungen werden echt gegen Licht, Walke, Decatur und schweflige Säure.Dyeing according to the method made known by D. R. P. 122284 becomes the shade bluish tint, and the colorations become real to light, fulling, decatur and sulphurous Acid.
Farbstoff Pikraminsäure- azo - ο -Dimethylamido-p-toluol-p-sulfamido- Coloring agent picric acid azo-ο -dimethylamido-p-toluene-p-sulfamido-
toluol.toluene.
Die Diazoverbindung aus 21,4 kg Pikraminsäure wird in gleicher Weise wie vorstehend beschrieben mit p-Toluol-sulfamidodimethylamidptoluol (Schmelzpunkt 1240)The diazo compound from 21.4 kg of picramic acid is treated in the same way as described above with p-toluene-sulfamidodimethylamidepotoluene (melting point 124 0 )
CH3 CH 3
IyN(CH3J2 IyN (CH 3 J 2
NH-SO2-C1Hi,NH-SO 2 -C 1 Hi,
welches aus p-Toluolsulfochlorid und unsymmetrisch dimethylirtem m-Toluylendiamin erhalten wird, combinirt; es entsteht ein Farbstoff, der auf Wolle mittelst Chrombeizen ein echtes tiefviolettes Bordeaux liefert.which consists of p-toluenesulfochloride and asymmetrical dimethylated m-toluenediamine is obtained, combined; a dye is created which delivers a real deep purple bordeaux on wool by means of chrome stains.
Beispiel III:Example III:
Farbstoff Pikraminsäure - azo - Di - ptoluol-p-sulfamido-m-amidobenzidin. Dye picric acid - azo - di - ptoluene-p-sulfamido-m-amidobenzidine.
m-Nitrobenzidin liefert bei der Einwirkung von 2 Mol. p-Toluolsulfochlorid ein bei 1640 schmelzendes Zwischenprodukt, welches durch darauf folgende Reduction in das bei 1980 schmelzende Di - ρ - Toluolsulfamido - amidodiphenyl folgender Constitution:m-nitrobenzidine provides upon exposure to 2 moles of p-toluenesulfonyl chloride in a 164 0-melting intermediate which by subsequent reduction in the melting at 198 0 Di - ρ - Toluolsulfamido - amidodiphenyl following constitution.:
NH2 C1 Hn - SO2-NH-(^ )-<( y~NH- SO2- C1H1 NH 2 C 1 H n - SO 2 -NH - (^ ) - <( y ~ NH- SO 2 - C 1 H 1
übergeführt wird. Läfst man auf 41 kg dieses Produktes, welches mit der erforderlichen Menge Natronlauge in ca. 1000 1 Wasser gelöst wurde, die Diazoverbindung aus 21,4 kg Pikraminsäure in einer durch Soda alkalisch gehaltenen Lösung einwirken, so entsteht ein Farbstoff, welcher auf Wolle bei Gegenwart von Chrombeizen tiefviolette Bordeauxtöne erzeugt.is convicted. If you run on 41 kg of this product, which one with the required Amount of sodium hydroxide solution was dissolved in about 1000 1 of water, the diazo compound from 21.4 kg If picric acid acts in a solution kept alkaline by soda, a Dye, which on wool in the presence of chrome stains has deep purple bordeaux tones generated.
Farbstoff Pikraminsäure-azo-o-Amidop-toluol-p-sulfamidochlorbenzol. Dye picric acid azo-o-amidop-toluene-p-sulfamidochlorobenzene.
Durch Wechselwirkung von o-Nitro-p-amidochlorbenzol (Ber. XX, 1379) und p-Toluolsulfochlorid entsteht ein Reactionsprodukt, welches bei 1420 schmilzt und durch darauffolgende Reduction das bei 1280 schmelzende o-Ainido-p-toluol-p-sulfamidochlorbenzol folgender Formel:By interaction of o-nitro-p-amidochlorbenzol (Ber., XX, 1379) and p-toluenesulfonyl a Reactionsprodukt which melts at 142 0 and by subsequent reduction, the 128 0 melting o-Ainido-p-toluene-p-sulfamidochlorbenzol arises following formula:
,NH., NH.
NH-SO2-C1H1 NH-SO 2 -C 1 H 1
liefert. Wenn 31,5 kg des letzteren in der vorstehend beschriebenen Weise mit der Diazoverbindung aus 21,4 kg Pikraminsäure combinirt werden, entsteht ein Farbstoff, welcher auf Wolle unter Anwendung von Chrombeizen ein echtes, gelbstichiges Bordeaux erzeugt. supplies. If 31.5 kg of the latter in the above-described manner combined with the diazo compound from 21.4 kg picric acid a dye is created, which is applied to wool with the use of chrome stains a real, yellowish Bordeaux produced.
Farbstoff Pikraminsäure-azo-o-Dimethylamido-i-Chlor-5-Nitrobenzol- Dye picric acid azo-o-dimethylamido-i-chloro-5-nitrobenzene-
p-sulfamid 0 toluol.p-sulfamide 0 toluene.
37 kg ο - Dimethylamido -1 -Chlor- 5 -Nitrobenzol-p-sulfamidotoluol (F. P. 1440) werden mit 4 kg Aetznatron in 400 1 Wasser gelöst und nach vorherigem Zusatz von 11 kg Soda werden zu dieser Lösung 21,4 kg diazotirte Pikraminsäure langsam hinzugegeben. Der erhaltene Farbstoff färbt gebeizte Wolle tiefviolett.37 kg of ο - dimethylamido -1-chloro-5-nitrobenzene-p-sulfamidotoluene (FP 144 0 ) are dissolved with 4 kg of caustic soda in 400 l of water and, after previous addition of 11 kg of soda, 21.4 kg of diazotized picric acid are added to this solution slowly added. The dye obtained dyes stained wool deep purple.
Farbstoff Nitroamidophenol - azo - o-Amido -p- chlorbenzol -p- sulfamid 0-Dye nitroamidophenol - azo - o-amido -p- chlorobenzene -p- sulfamide 0-
toluol.toluene.
Aus dem o-Nitro-p-amidotoluol und p-Chlorbenzolsulfochlorid (Beilstein, III. Aufl., Bd. II, S. n8) entsteht zunächst ein bei 1370 schmelzendes Combinationsprodukt, welches durch Reduction mit Zinkstaub und Salzsäure in das o-Amido-p-chlorbenzol-p-sulfamidotoluol folgender Formel übergeht:From o-nitro-p-amidotoluol and p-Chlorbenzolsulfochlorid (Beilstein, III. Ed., Vol. II, p n8) first formed a at 137 0 melting Combination product which by the reduction with zinc dust and hydrochloric acid in the o-amido -p-chlorobenzene-p-sulfamidotoluene goes over to the following formula:
CH.CH.
,NH., NH.
NH-NH-
Der so erhaltene Körper schmilzt bei 121 °.The body obtained in this way melts at 121 °.
29,6 kg dieses Produktes werden mit der Diazoverbindung aus 1 5,4 kg p-Nitro-o-Amidophenol combinirt. Der erhaltene Farbstoff erzeugt auf Wolle unter Verwendung von Chrombeizen ein Bordeaux.29.6 kg of this product are combined with the diazo compound from 1 5.4 kg of p-nitro-o-amidophenol combined. The dye obtained produces a Bordeaux on wool using chrome stains.
Beispiel VII:Example VII:
Farbstoff4-Nitro-6-amidosaIicylsäureazo-o-Amidobenzol-p-sulfamidotoluol. Dye 4-nitro-6-amidosaicylic acid azo-o-amidobenzene-p-sulfamidotoluene.
Das als Ausgangsmaterial für diesen Farbstoff dienende Amidosulfamid wird dargestellt durchThe amidosulfamide used as the starting material for this dye is represented by
Einwirkung von Benzolsulfochlorid auf o-Nitro-p-Amidotoluol; das zunächst erhaltene Reactionsprodukt, welches bei i6o° schmilzt, liefert bei der Reduction das bei 1380 schmelzende o-Amidobenzol-p-sulfamidotoluol.Action of benzene sulfochloride on o-nitro-p-amidotoluene; Reactionsprodukt the initially obtained, which melts at I6O °, provides for the reduction in the 138 0 o-melting amidobenzene-p-sulfamidotoluol.
26,2 kg des zuletzt genannten Produktes werden, am zweckmäßigsten in schwach atzalkalischer Lösung, mit der Diazoverbindung aus 10 kg 4-Nitro-6-amidosalicylsäure combinirt. Der entstehende Farbstoff färbt chrom26.2 kg of the last-named product, most appropriately in a slightly alkaline form Solution, combined with the diazo compound from 10 kg of 4-nitro-6-amidosalicylic acid. The resulting dye stains chrome
gebeizte Wolle in Tönen an.stained wool in tones.
sbhäflen gelblich rolhenyellowish rolhen
Claims (1)
Verfahren zur Darstellung von beizenfärbenden Monoazofarbstoffe!"), darin bestehend, dafs man die Diazoverbindung von Nitroderivaten des o-AmidophenoIs einwirken läfst auf m-Amidoarylsulfamide, in welchen die Parastellung zur Sulfamidogruppe besetzt ist.Patent Claim:. . '·. » .
Process for the preparation of mordant monoazo dyes! "), Consisting in allowing the diazo compound of nitro derivatives of o-amidophenol to act on m-amidoarylsulphamides in which the para position to the sulphamido group is occupied.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748473C (en) * | 1936-11-19 | 1944-11-03 | Process for the preparation of water-insoluble monoazo dyes | |
| DE1243137B (en) * | 1959-09-16 | 1967-06-29 | Ici Ltd | Process for dyeing textile materials |
| US5446425A (en) * | 1993-06-07 | 1995-08-29 | Atr Optical And Radio Communications Research Laboratories | Floating potential conductor coupled quarter-wavelength coupled line type directional coupler comprising cut portion formed in ground plane conductor |
| EP0887346A2 (en) * | 1997-06-23 | 1998-12-30 | F. Hoffmann-La Roche Ag | Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives, their preparation and their use as alpha1A/1L adrenoceptor agonists |
| EP1398022A1 (en) * | 2002-09-16 | 2004-03-17 | Kao Corporation | Hair dye composition comprising an azo dye containing a dissociative proton, method and use |
| EP1398020A1 (en) * | 2002-09-16 | 2004-03-17 | Kao Corporation | Hair dye composition comprising an azo dye containing a dissociative proton, method and use |
-
0
- DE DENDAT135016D patent/DE135016C/de active Active
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE748473C (en) * | 1936-11-19 | 1944-11-03 | Process for the preparation of water-insoluble monoazo dyes | |
| DE1243137B (en) * | 1959-09-16 | 1967-06-29 | Ici Ltd | Process for dyeing textile materials |
| US5446425A (en) * | 1993-06-07 | 1995-08-29 | Atr Optical And Radio Communications Research Laboratories | Floating potential conductor coupled quarter-wavelength coupled line type directional coupler comprising cut portion formed in ground plane conductor |
| EP0887346A2 (en) * | 1997-06-23 | 1998-12-30 | F. Hoffmann-La Roche Ag | Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives, their preparation and their use as alpha1A/1L adrenoceptor agonists |
| EP0887346A3 (en) * | 1997-06-23 | 1999-05-06 | F. Hoffmann-La Roche Ag | Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives, their preparation and their use as alpha1A/1L adrenoceptor agonists |
| US5952362A (en) * | 1997-06-23 | 1999-09-14 | Syntex (U.S.A) Inc. | 2-imidazoline, 2-oxazoline, 2-thiazoline, and 4-imidazole derivatives of methylphenyl, methoxyphenyl, and aminophenyl alkylsulfonamides and ureas and their use |
| US6057349A (en) * | 1997-06-23 | 2000-05-02 | F. Hoffman La Roche Ag | 2-imidazoline, 2-oxazoline, 2-thiazoline, and 4-imidazole derivatives of methylphenyl, methoxphenyl, and aminophenyl alkylsulfonamides and ureas and their use |
| EP1398022A1 (en) * | 2002-09-16 | 2004-03-17 | Kao Corporation | Hair dye composition comprising an azo dye containing a dissociative proton, method and use |
| EP1398020A1 (en) * | 2002-09-16 | 2004-03-17 | Kao Corporation | Hair dye composition comprising an azo dye containing a dissociative proton, method and use |
| US7056355B2 (en) | 2002-09-16 | 2006-06-06 | Kao Corporation | Hair dye composition and dyeing method |
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