DE256899C - - Google Patents
Info
- Publication number
- DE256899C DE256899C DENDAT256899D DE256899DA DE256899C DE 256899 C DE256899 C DE 256899C DE NDAT256899 D DENDAT256899 D DE NDAT256899D DE 256899D A DE256899D A DE 256899DA DE 256899 C DE256899 C DE 256899C
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- naphthol
- lacquers
- naphthylamine
- dye
- 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
- 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 claims description 5
- 239000004922 lacquer Substances 0.000 claims description 5
- 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 2
- 239000000975 dye Substances 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 a-naphthylamine sulfonic acids Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N alpha-aminonaphthalene Natural products C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002966 varnish 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
-
- 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
- C09B45/22—Monoazo compounds containing other metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAIKAI
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 256899 KLASSE 22 a. GRUPPE- M 256899 CLASS 22 a. GROUP
geeigneten Monoazofarbstoffe.suitable monoazo dyes.
Es wurde gefunden, daß man durch Kombination der Diazoverbindung aus i-Naphtylamin-2-sulfosäure mit 2-Naphtol-3-carbonsäure einen Farbstoff erhält, dessen Magnesium-, Mangan-, Strontium-, Barium- und insbesondere Calciumsalz sich durch eine schöne Violettfarbe ' bei vorzüglichen Echtheitseigenschaften auszeichnet.It has been found that by combining the diazo compound from i-naphthylamine-2-sulfonic acid with 2-naphthol-3-carboxylic acid a dye is obtained whose magnesium, Manganese, strontium, barium and especially calcium salts have a beautiful purple color '' with excellent fastness properties.
Es sind aus den Patentschriften 224880 und 226241 Azofarbstoffe bekannt, die zur Herstellung violetter Farblacke dienen sollen. Von diesen unterscheidet sich das neue Produkt sowohl durch seine Schönheit als auch durch die weit überlegene Lichtechtheit.There are known from the patents 224880 and 226241 azo dyes for the production violet colored lakes are intended to serve. The new product differs from these both by its beauty and by the far superior lightfastness.
In den Patentschriften 145915, 151205, 205080, 213499 sind zahlreiche Azofarbstoffe aus 2-Naphtol"3-carbonsäure beschrieben, die zur Herstellung von Farblacken Verwendung finden sollen. Es sind Kombinationen, die sich von Aminobenzolsulfosäuren und deren Derivaten oder von ß-Naphtylaminsulfosäuren ableiten und die durch Verlackung ausgesprochen rote Farbtöne geben.In the patents 145915, 151205, 205080, 213499 numerous azo dyes from 2-naphthol "3-carboxylic acid are described, the to find use for the production of colored lacquers. There are combinations that from aminobenzene sulfonic acids and their derivatives or from ß-naphtylamine sulfonic acids derive and give the distinct red color tones due to the varnish.
Dagegen hat von den zahreichen a-Naphtylaminsulfosäuren bisher noch keine Azokombination mit 2-Naphtol-3-carbonsäure eine technische Verwendung gefunden. Die meisten Kombinationen der a-Naphtylaminsulfosäuren mit 2-Naphtol-3-carbonsäure geben wenig schöne Lacke, die sich zu einer technischen Verwendung nicht eignen. Es lag somit außerhalb jeder Voraussicht, daß mittels der i-Naphtylamin-2-sulfosäure, welche bisher überhaupt keine technische Verwendung gefunden hat, mit 2-Naphtol-3-carbonsäure eine Azokombination erhalten werden kann, welche die beschriebenen technisch wertvollen Eigenschaften aufweist.On the other hand, of the many a-naphthylamine sulfonic acids So far, no azo combination with 2-naphthol-3-carboxylic acid has been used industrially. Most Combinations of the α-naphthylamine sulfonic acids with 2-naphtol-3-carboxylic acid give little beautiful lacquers, which become a technical one Not suitable for use. It was therefore beyond any foresight that by means of the i-Naphthylamine-2-sulfonic acid, which so far at all has found no technical use, an azo combination with 2-naphthol-3-carboxylic acid can be obtained which have the technically valuable properties described having.
Die Darstellung des neuen Farbstoffs bzw. der neuen Farblacke geschieht z. B. wie folgt:The presentation of the new dye or the new color lacquers is done, for. B. as follows:
Die in üblicherweise aus 245 kg 1 · 2-naphtylaminsulfosaurem Natrium hergestellte Diazoverbindung läßt man in eine mittels 380 kg Natronlage von 40 ° Be. und 60 kg Soda hergestellte wäßrige Lösung von 190 kg 2-Naphtol-3-carbonsäure einlaufen. Die Kupplung geht rasch vor sich.The usually from 245 kg 1 · 2-naphtylaminsulfosaurem Sodium produced diazo compound is left in a means of 380 kg Soda layer of 40 ° Be. and 60 kg of soda produced aqueous solution of 190 kg of 2-naphthol-3-carboxylic acid come in. The coupling is quick.
Zur Herstellung der Farblacke verfährt man weiter z. B. in folgender Weise:To produce the color lacquers, continue z. B. in the following way:
600 kg einer 20 prozentigen Paste des neuen Farbstoffs werden unter Zusatz von Türkisch-x rotöl mit Wasser tüchtig verrührt. Hierzu läßt man unter Umrühren eine entsprechende Menge des lackbildenden, in Wasser gelösten Salzes, z. B. etwa 80 kg Calciumchlorid, zulaufen. Die Masse wird noch so lange erhitzt, bis die Umsetzung vollendet ist. Es ist selbstverständlich, daß die Kupplung zum Farbstoff und dessen Überführung in den Farblack auch in einer Operation ausgeführt werden kann.600 kg of a 20 percent paste of the new dye are stirred efficient with the addition of Turkish-x red oil with water. For this purpose, a corresponding amount of the lacquer-forming salt dissolved in water, e.g. B. about 80 kg calcium chloride. The mass is heated until the conversion is complete. It goes without saying that the coupling to the dye and its conversion into the color lake can also be carried out in one operation.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE256899C true DE256899C (en) |
Family
ID=514868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT256899D Active DE256899C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE256899C (en) |
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0
- DE DENDAT256899D patent/DE256899C/de active Active
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