DE127140C - - Google Patents
Info
- Publication number
- DE127140C DE127140C DENDAT127140D DE127140DA DE127140C DE 127140 C DE127140 C DE 127140C DE NDAT127140 D DENDAT127140 D DE NDAT127140D DE 127140D A DE127140D A DE 127140DA DE 127140 C DE127140 C DE 127140C
- Authority
- DE
- Germany
- Prior art keywords
- bordeaux
- precipitation
- red
- bluish
- acid
- 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
- 238000001556 precipitation Methods 0.000 claims description 21
- 239000000975 dye Substances 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 5
- 235000020127 ayran Nutrition 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims description 4
- NUIURNJTPRWVAP-UHFFFAOYSA-N Tolidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 Wool Anatomy 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 claims 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-Methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- UEUGTXFKMNWFRE-UHFFFAOYSA-L Scarlet GN Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC(C)=C1N=NC1=CC=C(C(=CC=C2)S([O-])(=O)=O)C2=C1O UEUGTXFKMNWFRE-UHFFFAOYSA-L 0.000 description 1
- LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical compound CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- MRVNLKITQIBNKU-UKOJIYRKSA-L disodium;(4E)-4-(naphthalen-1-ylhydrazinylidene)-3-oxonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(N\N=C3/C4=CC=C(C=C4C=C(C3=O)S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 MRVNLKITQIBNKU-UKOJIYRKSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PLYDMIIYRWUYBP-UHFFFAOYSA-N ethyl 4-[[2-chloro-4-[3-chloro-4-[(3-ethoxycarbonyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-oxo-1-phenyl-4H-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=NN(C=2C=CC=CC=2)C(=O)C1N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(=N1)C(=O)OCC)C(=O)N1C1=CC=CC=C1 PLYDMIIYRWUYBP-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- -1 oxyazo Chemical group 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMI.PATENTAMI.
Durch Einwirkung von Acetyl-ßj · a3-amidonaphtol-ß4-sulfosäure auf die Zwischenproducte aus Paradiaminen und Oxycarbonsäuren der Benzolreihe erhält man gelblich bis bläulichbordeauxrothe Farbstoffe, welche Baumwolle ohne Beizen färben und sich durch gute Echtheitseigenschaften, besonders durch ganz hervorragende Lichtechtheit vor allen Substantiven Azofarbstoffe ähnlicher Nuance auszeichnen. Als Diamine können Verwendung finden Benzidin, Tolidin, Dianisidin etc., als Oxysäuren die Oxycarbonsäuren des Benzols und Homologe. The action of acetyl-ßj · a 3 -amidonaphtol-ß 4 -sulfonic acid on the intermediate products of paradiamines and oxycarboxylic acids of the benzene series gives yellowish to bluish-burgundy-red dyes, which dye cotton without staining and have good fastness properties, especially excellent lightfastness above all Identify nouns azo dyes of similar shade. Benzidine, tolidine, dianisidine etc. can be used as diamines, and the oxycarboxylic acids of benzene and homologues as oxyacids.
Während nun im Allgemeinen durch den Eintritt einer Acetylgruppe in das Molekül eines Oxyazofarbstoffes aus Amidonaphtolsulfosäure Nuancen erhalten werden, welche zwischen denen der entsprechenden Naphthol- und Amidonaphtolsulfosä'uren liegen, also eine Verschiebung nach der helleren Seite des Spectfums hin stattfindet, bildet die Acetyl-ßj · a3-amidonaphthol-ß4-sulfosäure hiervon eine nicht vorauszusehende Ausnahme: Die Nuancen der entsprechenden Farbstoffe aus ßj · c.3-Amidonaphtol-ß4-sulfosäure und Acetyl-ßj · a3-amidonaphtol-ß4-sulfosäure sind fast gar nicht verschieden. Unterscheidet sich also die Acetyl-P1 · a3 - amidonaphtol - S4 - sulfosäure hierdurch wesentlich von anderen Amidonaphtolsulfosäuren, so übertreffen die daraus dargestellten Farbstoffe diejenigen aus nicht acetylirter ßl · a3-Amidonaphtol - ß4 - sulfosäure, aufserordentlich durch ihren technischen Werth. Die Säureechtheit ist bedeutend verbessert und die Lichtechtheit derart erhöht, dafs die Farbstoffe in dieser Beziehung den besten Producten mindestens gleichgestellt werden müssen; es stellt also die Erfindung einen grofsen technischen Effect dar.While the entry of an acetyl group into the molecule of an oxyazo dye made from amidonaphthol sulfonic acid results in nuances which lie between those of the corresponding naphthol and amidonaphthol sulfonic acids, i.e. there is a shift towards the lighter side of the spectrum, the acetyl-βj · A 3 - amidonaphthol-ß 4 -sulfonic acid an unforeseeable exception: the nuances of the corresponding dyes from ßj · c. 3- Amidonaphtol-ß 4 -sulfonic acid and acetyl-ßj · a 3 -amidonaphtol-ß 4 -sulfonic acid are almost no different. Thus differs acetyl-P 1 · a 3 - amidonaphtol - S 4 - sulfonic acid thereby significantly from other Amidonaphtolsulfosäuren, the dyes represented therefrom surpass those of non acetylirter ß l · a 3 -Amidonaphtol - ß 4 - sulfonic acid, extraordinarily by their technical value The fastness to acid is considerably improved, and the fastness to light is so increased that the dyestuffs in this respect must at least be equated with the best products; the invention thus represents a great technical effect.
Farbstoff ausDye off
BenzidinBenzidine
^Salicylsäure
Acetyl-ßj · a3-amidonaphtol-ß4-sulfo-^ Salicylic Acid
Acetyl-ßja 3 -amidonaphtol-ß 4 -sulfo-
säure:acid:
9,2 Theile Benzidin werden in 28,5 Theilen Salzsäure von 200 Be. und 300 Theilen Wasser gelöst und bei 50C. mit einer Lösung von 7 Theilen Natriumnitrit in 50 Theilen Wasser tetrazotirt. Die Tetrazolösung wird in eine eiskalte Lösung von 7,3 Theilen Salicylsäure und 24 Theilen Soda in 400 Theilen Wasser einlaufen gelassen. Nach beendeter Zwischenproductsbildung fügt man eine Lösung von 14,8 Theilen Acetyl-ßx · a3-amidonaphthol-ß4-sulfosäure zu und läfst zur Vollendung der Combination 24 Stunden stehen; hierauf wärmt man langsam auf 80 bis 900C, fällt mit Salz und trocknet. Der Farbstoff färbt Baumwolle ohne Beizen gelblich bordeauroth. An Stelle von Benzidin kann Tolidin, Dianisidin oder Paraphenylendiamin, an Stelle von Salicylsäure können die Kresotinsäuren Verwendung finden.9.2 parts of benzidine are dissolved in 28.5 parts of hydrochloric acid of 20 ° Be. dissolved and 300 parts of water and tetrazotirt at 5 0 C. with a solution of 7 parts sodium nitrite in 50 parts of water. The tetrazo solution is poured into an ice-cold solution of 7.3 parts salicylic acid and 24 parts soda in 400 parts water. After the formation of intermediate products has ended, a solution of 14.8 parts of acetyl-β x · a 3 -amidonaphthol-β 4 -sulfonic acid is added and the mixture is left for 24 hours to complete the combination; then it is slowly warmed to 80 to 90 ° C., precipitated with salt and dried. Without staining, the dye dyes cotton yellowish bordeaux-red. Tolidine, dianisidine or paraphenylenediamine can be used instead of benzidine, and cresotinic acids can be used instead of salicylic acid.
Die folgende Tabelle enthält die Eigenschaften aller nach dem vorliegenden Verfahren darstellbaren Farbstoffe.The following table contains the properties of all made by the present method representable dyes.
und zum Farbstoff combinirt mit ßj-Acetyland combined with βj-acetyl to form the dye
sehen des
Farb
stoffesthe end
see the
Color
fabric
LösungThe o, i proc. watery
solution
Natron
laugeon add
Baking soda
lye
Salz
säureatz of
salt
acid
Lösung
in cone. .
Schwefel
säure
istthe
solution
in cone. .
sulfur
acid
is
Farbstoff
färbt
un
geheizte
Baum
wolleOf the
dye
colors
U.N
heated
tree
wool
sehen des
Farb
stoffesthe end
see the
Color
fabric
Benzidin I.
Benzidine
braunes
Pulverred
brown
powder
Fällungrothe
precipitation
Fällungtan
precipitation
blaureddish
blue
ziegel-
rothbluish
brick-
red
Pulverbrown
powder
Tolidin 2.
Tolidine
Pulverbrown
powder
rothyellow-
red
Fällungbordeaux
precipitation
braune
Fällungred
tan
precipitation
bordeauxyellowish
bordeaux
Pulverbrown
powder
Dianisidin3 ·
Dianisidine
braunes
Pulverblack
brown
powder
Fällungbordeaux
precipitation
Fällungpurple
precipitation
bordeauxbluish
bordeaux
braunes
Pulverblack
brown
powder
p-Phenylendiamin4 ·
p-phenylenediamine
schwar
zes
PulverBrown
black
zes
powder
bordeauxbluish
bordeaux
Fällungrothe
precipitation
blaugreenish
blue
bordeauxbluish
bordeaux
schwar
zes
PulverBrown
black
zes
powder
Claims (1)
Salz
säureitz from
salt
acid
Lösung
in cone.
Schwefel
säure
istthe
solution
in cone.
sulfur
acid
is
Farbstoff
färbt
un
geheizte
Baum
wolleOf the
dye
colors
U.N
heated
tree
wool
sehen des
Farb
stoffesthe end
see the
Color
fabric
LösungThe 0.1 proc. watery
solution
Natron
laugeon add
Baking soda
lye
Salz
säureatz of
salt
acid
Lösung
in cone.
Schwefel
säure
istthe
solution
in cone.
sulfur
acid
is
Farbstoff
färbtOf the
dye
colors
Lösungproc. watery
solution
Fällungtan
precipitation
ziegel-
rothbluish
brick-
red
Pulverbrown
powder
rothe
Fällungbluish
rothe
precipitation
braune
Fällungred
tan
precipitation
geheizte
Baum
wolleU.N
heated
tree
wool
Natron
laugeon add
Baking soda
lye
braune
Fällungred
tan
precipitation
bordeauxbluish
bordeaux
Pulverbrown
powder
rothyellow-
red
Fällungbordeaux
precipitation
Fällungbordeaux
precipitation
ziegel-
rothbluish
brick-
red
Fällungro the
precipitation
violette
Fällungbluish
purple
precipitation
grünblue
green
bordeauxbluish
bordeaux
braunes
Pulverblack
brown
powder
Fällungbordeaux
precipitation
Fällungpurple
precipitation
grünblue
green
Fällungbordeaux
precipitation
Fällungbordeaux
precipitation
grünblue
green
bordeauxyellowish
bordeaux
schwar
zes
PulverBrown-
black
zes
powder
bordeauxbluish
bordeaux
Fällungrothe
precipitation
blaugreenish
blue
bordeauxbluish
bordeaux
Fällungbordeaux
precipitation
bordeaux.yellowish
bordeaux.
bordeauxbluish
bordeaux
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE127140C true DE127140C (en) |
Family
ID=395755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT127140D Active DE127140C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE127140C (en) |
-
0
- DE DENDAT127140D patent/DE127140C/de active Active
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