DE205080C - - Google Patents
Info
- Publication number
- DE205080C DE205080C DE1906205080D DE205080DA DE205080C DE 205080 C DE205080 C DE 205080C DE 1906205080 D DE1906205080 D DE 1906205080D DE 205080D A DE205080D A DE 205080DA DE 205080 C DE205080 C DE 205080C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- acid
- red
- parts
- melting point
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 10
- 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 description 3
- 241000947840 Alteromonadales Species 0.000 claims 1
- NPAYBXSLOLNULX-UHFFFAOYSA-N 2-diazo-1H-naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)C(=[N+]=[N-])C=CC2=C1 NPAYBXSLOLNULX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001809 detectable Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000010428 oil painting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000004575 stone 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
- C09B29/14—Hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Patentiert im Deutschen Reiche vom 15. April 1906 ab.Patented in the German Empire on April 15, 1906.
Von den vielen Azofarbstoffen, welche sich für die Herstellung roter Farblacke eignen, kommen· für die Erzielung stark blaustichig roter Nuancen von großer Reinheit des Tons und guten Echtheitseigenschaften nur sehr wenige Farbstoffe in Betracht, zumal wenn auch den übrigen Anforderungen der Lackfarbenindustrie genügend Rechnung getragen werden soll.Of the many azo dyes that are are suitable for the production of red colored lacquers, come · to achieve a strong bluish cast red nuances of great purity of the tone and good fastness properties only very few dyes in consideration, especially if the other requirements of the paint industry sufficient account should be taken.
ίο Es wurde nun gefunden, daß der Monoazofarbstoff aus |3-Oxynaphthoesäure-2 · 3 (Schmelzpunkt 2i6°) mit 2-Diazonaphthalin-i-sulfosäure Farblacke von ganz besonderem Wert liefert. Diese Lacke zeigen nämlich große Farbkraft und einen Blaustich der Nuance, wie es bisher nur mit dem Farbstoff der Patentschrift 163644 in annähernder Reinheit erhalten werden konnte. Indessen zeichnen sich die Farblacke aus dem nach vorliegendem Verfahren erhältlichen Farbstoff vor demjenigen dieses bekannten Farbstoffs durch ihre erheblich höhere Lichtechtheit aus. Der um die Carboxylgruppe ärmere Farbstoff aus 2-Diazonaphthalini-sulfosäure und ß-Naphthol der Patentschrift 112833 liefert weit gelbstichigere Lacke, die, wenn es sich um die Herstellung von blauroten Bordeauxnuancen handelt, nicht in Betracht kommen können. Die Lacke eignen sich' vorzüglich zur Verwendung im Buch-, Stein- und Blechdruck sowie für ölanstriche. Die Darstellung des neuen Farbstoffs geschieht z. B. wie folgt:ίο It has now been found that the monoazo dye from | 3-oxynaphthoic acid-2 · 3 (melting point 26 °) with 2-diazonaphthalene-i-sulfonic acid Provides colored lacquers of very special value. This is because these paints show great color strength and a bluish tint of the shade, as was previously only possible with the dye of the patent specification 163644 could be obtained in approximate purity. Meanwhile, the colored lakes stand out from the dye obtainable by the present process before that of this known dye due to their significantly higher lightfastness. The one around the carboxyl group poorer dye made from 2-diazonaphthalenesulfonic acid and ß-naphthol of patent specification 112833 provides varnishes with a far more yellowish tinge, which, when it comes to the production of blue-red burgundy nuances, not considered can come. The varnishes are ideal for use in books, Stone and metal printing as well as for oil painting. The new dye is displayed z. B. as follows:
Man löst 24,5 Teile 2-naphthylamin-i-sulfosaures Natron nebst wenig mehr als der äquivalenten Menge Natriumnitrit in der nötigen Menge Wasser und läßt die kalt gehaltene Lösung in kalte verdünnte Salzsäure einfließen, welche etwas mehr als 2 Äquivalente Chlorwasserstoff enthält, so daß nach beendeter Diazotierung noch Säureüberschuß vorhanden und salpetrige Säure deutlich nachweisbar ist. Die so erhaltene Diazolösung läßt man langsam in eine mit der nötigen Menge Wasser hergestellte Lösung von 20 Teilen ß-Oxynaphthoesäure-2 · 3 (Schmelzpunkt 216c) nebst 25 Teilen Natronlauge von 40 ° Be. und etwa 6 Teilen calcinierter Soda einlaufen. Die Farbstoffbildung ist in kurzer Zeit beendet. Der rote Farbstoff, welcher meist völlig abgeschieden ist, wird auf die übliche Weise isoliert und zweckmäßig in Pastenform für die Farblackbereitung angewendet; er kann jedoch auch, da seine Wasserlöslichkeit eine genügende ist, in Pulverform hergestellt und verwendet werden.24.5 parts of 2-naphthylamine-i-sulfonic acid sodium and a little more than the equivalent amount of sodium nitrite are dissolved in the necessary amount of water and the solution, which is kept cold, is poured into cold dilute hydrochloric acid, which contains a little more than 2 equivalents of hydrogen chloride, so that after the end of the diazotization, excess acid is still present and nitrous acid is clearly detectable. The diazo solution obtained in this way is slowly poured into a solution of 20 parts of β-oxynaphthoic acid 2 · 3 (melting point 216 c ) and 25 parts of sodium hydroxide solution at 40 ° Be, prepared with the necessary amount of water. and pour in about 6 parts of soda ash. The dye formation is complete in a short time. The red dye, which is usually completely separated, is isolated in the usual way and used appropriately in paste form for the preparation of colored lacquers; however, since its water solubility is sufficient, it can also be prepared and used in powder form.
■Patent-Anspruch :■ Patent claim:
Verfahren zur Darstellung eines roten, besonders für die Herstellung blauroter Farblacke geeigneten Monoazofarbstoffe, darin bestehend, daß man 2-Diazonaphthalin-1-sulfosäure mit ß-Oxynaphthoesäure-2·3 (Schmelzpunkt 216°) vereinigt.Process for the representation of a red, especially for the production of blue-red Color lakes suitable monoazo dyes, consisting in that one 2-diazonaphthalene-1-sulfonic acid with ß-oxynaphthoic acid-2 · 3 (Melting point 216 °) combined.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT40679D AT40679B (en) | 1906-04-14 | 1908-12-28 | Process for the production of a red monoazo dye, particularly suitable for the production of blue-red colored lakes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE205080C true DE205080C (en) |
Family
ID=467353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1906205080D Expired - Lifetime DE205080C (en) | 1906-04-14 | 1906-04-14 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE205080C (en) |
-
1906
- 1906-04-14 DE DE1906205080D patent/DE205080C/de not_active Expired - Lifetime
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