DE139286C - - Google Patents
Info
- Publication number
- DE139286C DE139286C DENDAT139286D DE139286DA DE139286C DE 139286 C DE139286 C DE 139286C DE NDAT139286 D DENDAT139286 D DE NDAT139286D DE 139286D A DE139286D A DE 139286DA DE 139286 C DE139286 C DE 139286C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- naphthol
- sulfonic acid
- ether
- diazotized
- 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 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- -1 hydroquinone dialkyl ether Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N 4-Methylphenol Natural products CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß mit Hülfe des bis jetzt zur Darstellung von Farbstoffen noch nicht benutzten Monoacetyl-ρ-diamidohydrochinondialkyla'thers It has been found that with the help of the up to now for the representation of dyes not yet used monoacetyl-ρ-diamidohydroquinonedialkyla'thers
O Alkyl O alkyl
ca·ca
O Alkyl O alkyl
sehr wertvolle blaue bis blauschwarze Farbstoffe erhalten werden können, wenn man diesen Äther diazotiert, mit i-Naphtylamin-6-bezw. -7-monosulfosäure kombiniert, die entstandene Amidoazoverbindung weiter diazotiert, mit 2-Naphtol-6-sulfosäure oder mit 2-Amido-8-naphtol-6-sulfosä'ure kuppelt und dann die Acetylgruppe abspaltet.very valuable blue to blue-black dyes can be obtained if one diazotized this ether, with i-naphtylamine-6-respectively. -7-monosulfonic acid combined, the resulting Amidoazo compound further diazotized with 2-naphthol-6-sulfonic acid or with 2-amido-8-naphthol-6-sulfonic acid couples and then splits off the acetyl group.
Durch Verwendung des Hydrochinondialkylä'thers an Stelle des im französischen Patent 307719 genannten p-Kresolalkyla'thers wird ein viel grünstichigeres und reineres Blau erzielt, als bisher mit Hülfe von Diazotierungsfarbstoffen überhaupt möglich war.By using the hydroquinone dialkyl ether instead of the one in the French patent 307719 called p-cresol alkyl ether is a Much greener and purer blue is achieved than before with the aid of diazotization dyes was even possible.
Die so erhaltenen Farbstoffe können auf ungebeizter Baumwolle fixiert werden und ergeben durch Diazotieren auf der Faser und Entwickeln mit ß-Naphtol vollkommen echte blaue bis blauschwarze Färbungen.The dyes obtained in this way can be fixed on unstained cotton and give by diazotizing on the fiber and developing with ß-naphtol completely real blue to blue-black colors.
Den bis jetzt noch nicht beschriebenen Monoacetyl - ρ -' diamidohydrochinondimethyläther kann man erhalten, wenn man Amidohydrochinondimethylä'ther (vergl. Magatti, Ber. XIV, 71, Mühlhäuser, Ann. 207, 254, Bä'ssler, Ber. XVII, 2119) acetyliert und in üblicher Weise nitriert und reduziert, oder wenn man denselben mit einer Diazoverbindung kombiniert, die so erhaltene Amidoazoverbindung acetyliert, dann reduziert und die Komponenten trennt.The so far not yet described monoacetyl - ρ - 'diamidohydroquinone dimethyl ether can be obtained by using amidohydroquinone dimethyl ether (see Magatti, Ber. XIV, 71, Mühlhäuser, Ann. 207, 254, Bä'ssler, Ber. XVII, 2119) acetylated and in usual way nitrated and reduced, or if you have the same with a diazo compound combined, the amidoazo compound thus obtained acetylated, then reduced and the Separates components.
Auf dieselbe Weise kann auch der entsprechende Äthyläther dargestellt werden..The corresponding ethyl ether can be represented in the same way.
Monoacetyl-ρ-diamidohydrochinondimethyläther wird in üblicher Weise diazotiert und mit der äquivalenten Menge i-Naphtylamin-6-bezw. -7-monosulfosä'ure gekuppelt. Die erhaltene Amidoazoverbindung wird dann nochmals diazotiert, mit 2-Naphtol-6-sulfosäure gekuppelt und darauf in üblicher Weise die Acetylgruppe abgespalten.Monoacetyl-ρ-diamidohydroquinone dimethyl ether is diazotized in the usual way and with the equivalent amount of i-naphtylamine-6-respectively. -7-monosulfonic acid coupled. The received The amidoazo compound is then diazotized again and coupled with 2-naphthol-6-sulfonic acid and then split off the acetyl group in the usual way.
Der so erhaltene Farbstoff stellt nach dem Trocknen ein dunkles Pulver dar und färbt ungeheizte Baumwolle in blauen Tönen an. Die Färbung geht beim Diazotieren auf der Faser und Entwickeln mit ß-Naphtol in ein waschechtes Blau über.The dye thus obtained is a dark powder after drying and colors unheated cotton in blue tones. The color goes when diazotizing on the Fiber and develop into a washable blue with ß-naphtol.
Wird in diesem Beispiel die 2-Naphtol-6-sulfosäure durch eine äquivalente Menge 2-Amido-8-naphtol-6-sulfosäure ersetzt, so gelangt man zu einem blauschwarzen Farbstoff, der durch Diazotieren auf der Faser und Entwickeln mit den bekannten Entwicklern, wie z.B. ß-Naphtol, m-Phenylendiamin, m-Toluylendiamin, Resorcin usw., in ein waschechtes Blauschwarz übergeht.In this example, 2-naphthol-6-sulfonic acid is used replaced by an equivalent amount of 2-amido-8-naphthol-6-sulfonic acid, so gets a blue-black dye which is diazotized on the fiber and developed with the well-known developers, such as ß-naphthol, m-phenylenediamine, m-tolylenediamine, Resorcinol, etc., turns into a true blue-black.
Durch die Verwendung des Diä'thyläthers an Stelle des oben genannten Dimethyläthers werden die Resultate nur unwesentlich beeinflußt.By using the diethyl ether in place of the above-mentioned dimethyl ether only marginally influenced the results.
Die charakteristischen Eigenschaften der Farbstoffe sind in nachfolgender Tabelle zusammengestellt :The characteristic properties of the dyes are summarized in the table below :
des
Farb
stoffesAppearance
of
Color
fabric
der
Lösung
in
Wassercolour
the
solution
in
water
Zusatz
von
Am
moniakTo
additive
from
At the
moniak
Lösung
in konz.
Schwefel
säureColor of
solution
in conc.
sulfur
acid
Ver
dünnen
mit
WasserTo
Ver
thin
with
water
Färbung
auf
Baum
wolleDirect
coloring
on
tree
wool
und ent
wickelt
mit
ß-NaphtolDiazotized
and ent
wraps
with
ß-naphtol
mit 2 · 6-Naphtolsulfosäuredye
with 2x6-naphthol sulfonic acid
dunkles
Pulvermetalgl.
dark
powder
blauviolet
blue
blauersome
bluer
violette
LösungRed
purple
solution
blauviolet
blue
blaugreenish
blue
2 · 8 · 6 - AmidonaphtolsulfosäureDye with
2 x 8 x 6 - amidonaphthol sulfonic acid
braunes
Pulverdark
brown
powder
blaudark
blue
blauersome
bluer
violetter
Nieder-,
schlagRed
purple
Low-,
blow
blaudark
blue
schwarz.blue
black.
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE139286C true DE139286C (en) |
Family
ID=407043
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT139286D Active DE139286C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE139286C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2359883A1 (en) * | 1976-07-28 | 1978-02-24 | Sandoz Sa | NEW DISAZOIC DYES AND THEIR PREPARATION |
-
0
- DE DENDAT139286D patent/DE139286C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2359883A1 (en) * | 1976-07-28 | 1978-02-24 | Sandoz Sa | NEW DISAZOIC DYES AND THEIR PREPARATION |
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