DE638338C - Process for the preparation of dyes of the safranine series - Google Patents
Process for the preparation of dyes of the safranine seriesInfo
- Publication number
- DE638338C DE638338C DEI46290D DEI0046290D DE638338C DE 638338 C DE638338 C DE 638338C DE I46290 D DEI46290 D DE I46290D DE I0046290 D DEI0046290 D DE I0046290D DE 638338 C DE638338 C DE 638338C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- series
- preparation
- safranine
- sulfonic 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 14
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical class [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- REZUOOCBJKWTSZ-UHFFFAOYSA-N 2-amino-5-(diethylamino)benzenesulfonic acid Chemical compound CCN(CC)C1=CC=C(N)C(S(O)(=O)=O)=C1 REZUOOCBJKWTSZ-UHFFFAOYSA-N 0.000 description 2
- -1 4-sulfophenyl- Chemical group 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JVFCJUNEJLISTR-UHFFFAOYSA-N 2-amino-3-(diethylamino)benzenesulfonic acid Chemical compound NC1=C(N(CC)CC)C=CC=C1S(=O)(=O)O JVFCJUNEJLISTR-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- C09B17/00—Azine dyes
- C09B17/04—Azine dyes of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von Farbstoffen der Safraninreihe Es wurde gefunden, daß man wertvolle Farbstoffe der Safraninreihe dadurch erhält, daß man Isorosindulin-6-sulfosäuren der allgemeinen Formel worin R und R1 Alkyl, Aralkyl oder Aryl bedeuten und worin die Kerne weitersubstituiert sein können, mit 4-Aminophenylarylamin-2-sulfosäuren, deren Homologen oder Substitutionsprodukten umsetzt. Die so -erhältlichen Farbstoffe entsprechender allgemeinen Formel worin R und R1 Alkyl, Aralkyl oder Aryl bedeuten, worin Ar für Aryl steht und worin die Kerne weitersubstituiert werden können.Process for the preparation of dyes of the safranin series It has been found that valuable dyes of the safranin series are obtained by using isorosindulin-6-sulfonic acids of the general formula where R and R1 are alkyl, aralkyl or aryl and where the nuclei can be further substituted, with 4-aminophenylarylamine-2-sulfonic acids, their homologues or substitution products. The dyes obtainable in this way correspond to the general formula where R and R1 are alkyl, aralkyl or aryl, where Ar is aryl and where the nuclei can be further substituted.
Sie zeichnen sich durch Klarheit des Farbtones und durch gute färberische Eigenschaften, insbesondere auch gute Alkäliechtheit, aus. Dies ist überraschend, da nach deri Angaben in der Literatur erwartet werden mußte, daß nur solche Farbstoffe der Naphthophenosafraninreihe, die die Sulfonsäuregruppe in der I6-Stellung besitzen, alkaliechte Färbungen liefern. Es ist ferner überraschend, daß bei den Farbstoffen diese Reihe mit I7-ständiger Sulfonsäuregruppe die Art der Substitution in der Aminogruppe @@ der I8-Stellung einen erheblichen Einfluß aü@ die Eigenschaften der Farbstoffe-ausübt insofern, als nur die Monosubstitutionsprodukte alkaliechte Färbungen liefern. Beispiel I Die in üblicher Weise aus 32,9 4-Sulfophenyl-ß-naphthylamin (Na-Salz) und 26,5 g Aminodiäthylanilin-3-sulfosäure (Na-Salz) hergestellte Isorosindulin-I₧6₧I3-trisulfosvgre wird in wäßriger Lösung mit 28g Aminodiphenylamin-2-sulfosäure (Na-Salz) unter Zusatz von 2o g Natriumacetat krist. erwärmt. Der erhaltene Farbstoff der wahrscheinlichen Formel kristallisiert beim Erkalten aus. Er löst sich in Wasser grünstichigblau, in konzentrierter Schwefelsäure grasgrün und färbt Wolle licht- und waschecht in reinen grünstichigblauen Tönen.They are distinguished by the clarity of the hue and by good coloring properties, in particular also good alkali fastness. This is surprising since, according to the information in the literature, it was to be expected that only those dyes of the naphthophenosafranine series which have the sulfonic acid group in the 16-position give alkali-fast colorations. It is also surprising that the type of substitution in the amino group of the 18 position has a considerable influence on the properties of the dyes, insofar as only the monosubstitution products provide alkaline colorations. EXAMPLE I The isorosindulin-I ₧ 6 ₧ I3-trisulfosvgre prepared in the usual way from 32.9 4-sulfophenyl-ß-naphthylamine (Na salt) and 26.5 g of aminodiethylaniline-3-sulfonic acid (Na salt) is in aqueous solution Solution with 28g aminodiphenylamine-2-sulfonic acid (Na salt) with the addition of 20 g of sodium acetate crystalline. warmed up. The obtained dye of the likely formula crystallizes out on cooling. It dissolves greenish blue in water, grass green in concentrated sulfuric acid and dyes wool lightfast and washable in pure greenish blue tones.
Beispiel 2 Die aus 23,59 o-Tolyl-ß-Naphthylamin und 26,5 g 4-aminodiäthylanilin-3-sulfosaurem Natrium hergestellte Isorosindulin-I ₧ 6-disulfosäure wird in wäßriger oder verdünnter alkoholischer Lösung mit 2'-Methoxy-4-aminodiphenylamin-2-sulfosäure, wie in Beispiel I beschrieben, umgesetzt. Der erhaltene Farbstoff der wahrscheinlichen Formel löst sich in konzentrierter Schwefelsäure grasgrün, in heißem Wasser klar blau und färbt Wolle licht-, wasch- und walkecht in reinen blauen Tönen.EXAMPLE 2 The isorosindulin-I ₧ 6-disulfonic acid prepared from 23.59 o-tolyl-ß-naphthylamine and 26.5 g of 4-aminodiethylaniline-3-sulfonic acid is dissolved in aqueous or dilute alcoholic solution with 2'-methoxy-4- aminodiphenylamine-2-sulfonic acid, as described in Example I, implemented. The obtained dye of the likely formula dissolves grass-green in concentrated sulfuric acid, clear blue in hot water and dyes wool in pure blue tones that are lightfast, washfast and washfast.
Beispiel 3 Die in üblicher Weise aus 30 g 2 - 5-Dichlorphenyl-ß-naphthylamin und 26 g 4-Aminodiäthylanilin-3-sulfosäure (Na-Salz) hergestellte Isorosindulin-I ₧ 6-disulfosäure wird in wäßriger Lösung mit 2 -Methoxy-4 - amzuodiphenylamin - 2 - sulfonsäure, wie in Beispiel I beschrieben, umgesetzt. Der erhaltene Farbstoff der wahrscheinlichen Formel mel löst sich in konzentrierter Schwefelsäure grasgrün, in Wasser klar grünstichigblau. Er färbt Wolle gut -egalisierend licht= und waschecht in sehr klären grünstichigblauen Tönen. Der in analoger Weise hergestellte Farbstoff der Formel hat ähnliche Eigenschaften.Example 3 The isorosindulin-I ₧ 6-disulfonic acid prepared in the usual way from 30 g of 2-5-dichlorophenyl-ß-naphthylamine and 26 g of 4-aminodiethylaniline-3-sulfonic acid (Na salt) is in aqueous solution with 2-methoxy 4 - amzuodiphenylamine - 2 - sulfonic acid, as described in Example I, reacted. The obtained dye of the probable formula mel dissolves grass green in concentrated sulfuric acid, clear greenish blue in water. It dyes wool well - leveling light = and washable in very clear greenish blue tones. The dye of the formula prepared in an analogous manner has similar properties.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI46290D DE638338C (en) | 1933-01-15 | 1933-01-15 | Process for the preparation of dyes of the safranine series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI46290D DE638338C (en) | 1933-01-15 | 1933-01-15 | Process for the preparation of dyes of the safranine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE638338C true DE638338C (en) | 1936-11-13 |
Family
ID=7191721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI46290D Expired DE638338C (en) | 1933-01-15 | 1933-01-15 | Process for the preparation of dyes of the safranine series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE638338C (en) |
-
1933
- 1933-01-15 DE DEI46290D patent/DE638338C/en not_active Expired
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