DE70234C - Process for the preparation of stain-coloring dyes from anthradichinones and phenols - Google Patents
Process for the preparation of stain-coloring dyes from anthradichinones and phenolsInfo
- Publication number
- DE70234C DE70234C DENDAT70234D DE70234DA DE70234C DE 70234 C DE70234 C DE 70234C DE NDAT70234 D DENDAT70234 D DE NDAT70234D DE 70234D A DE70234D A DE 70234DA DE 70234 C DE70234 C DE 70234C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- violet
- acid
- red
- phenols
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 18
- 239000000975 dye Substances 0.000 title claims description 10
- 150000002989 phenols Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims 5
- 238000004040 coloring Methods 0.000 title claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- 229960004889 salicylic acid Drugs 0.000 claims description 7
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 claims description 2
- NJESAXZANHETJV-UHFFFAOYSA-N 4-Methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 2
- 150000004345 1,2-dihydroxyanthraquinones Chemical class 0.000 claims 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N O-Cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims 1
- 150000004053 quinones Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 240000000358 Viola adunca Species 0.000 description 10
- 235000005811 Viola adunca Nutrition 0.000 description 10
- 235000013487 Viola odorata Nutrition 0.000 description 10
- 235000002254 Viola papilionacea Nutrition 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000875 corresponding Effects 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- VBHKTXLEJZIDJF-UHFFFAOYSA-N Quinalizarin Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1O VBHKTXLEJZIDJF-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- -1 cresol carboxylic acid Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
- C09B1/14—Dyes containing ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Läfst man die in der Patentschrift Nr. 66153 charakterisirten Anthradich.inone (Alizarincyaninchinone) auf Phenole oder deren Substitutionsproducte einwirken, so gelängt man zu einer Reihe neuer, technisch werthvoller beizenfärbender Farbstoffe. Den bei dieser Reaction erhaltenen quantitativen - Resultaten zufolge scheint 1 Mol. des betreffenden Anthradichinons mit ι Mol. des Phenols zusammenzutreten.If you read the in patent specification No. 66153 characterized anthradichinones (alizarincyaninequinones) on phenols or their substitution products one arrives at a number of new, technically valuable stain-coloring agents Dyes. According to the quantitative results obtained in this reaction 1 mole of the anthradichinone in question appears to come together with ι mole of the phenol.
Die Vereinigung beider Compdnenten geschieht am besten in schwefelsaurer Lösung und geht schon bei gewöhnlicher Temperatur von Statten. Zweckmäfsig vereinigt man die Darstellung des Anthradichinons und die Combination desselben mit dem. anzuwendenden Phenol zu einer einzigen zusammenhängenden Operation.The combination of both components is best done in a sulfuric acid solution and works even at normal temperature. The representation of the Anthradichinons and the combination of the same with that. applicable phenol to a single contiguous operation.
10 kg trockenes Alizarinbordeaux werden in 200 kg Schwefelsäure von 66° B. gelöst und nach ;den Angaben der Patentschrift Nr. 66153 und unter Einhaltung der dort angegebenen Vorsichtsmafsregeln mit 10 kg Braunstein oxydirt.10 kg of dry alizarin bordeaux are used in 200 kg of sulfuric acid of 66 ° B. dissolved and according to the specifications of patent specification No. 66153 and, in compliance with the precautionary rules given there, oxidized with 10 kg of manganese dioxide.
In die so erhaltene schwefelsaure Lösung des in der Patentschrift Nr. 66153 a's Chinon des Pentacyanins bezeichneten Farbstoffes werden nach und nach 10 kg Salicylsäure eingetragen, indem man die Temperatur nicht über 25 ° steigen läfst. Die Reaction giebt sich durch die Aenderung ■ der Farbe der schwefelsauren Lösung von 'Blau in Blaugrün zu erkennen.In the thus obtained sulfuric acid solution of the dye referred to in the patent no. 66153 A 's of the quinone Pentacyanins be added gradually 10 kg of salicylic acid by not rise above 25 ° läfst temperature. The reaction can be recognized by the change in the color of the sulfuric acid solution from blue to blue-green.
Durch Umrühren befördert man die Reaction und giefst nach etwa 18 Stunden die Masse in 2000 1 Wasser, kocht auf, filtrirt den* abgeschiedenen . Farbstoff ab und wäscht neutral. Durch Lösen in Natronlauge, Filtriren der alkalischen Lösung und Ausfällen mit einer Säure wird das neue Product weiter gereinigt.The reaction is promoted by stirring and, after about 18 hours, the mass is poured in 2000 1 water, boils, filters the * separated . Dye off and washes neutral. By dissolving in sodium hydroxide solution, filtering the alkaline solution and precipitating with a The new product is further cleaned with acid.
So dargestellt, bildet es eine dunkelviolette Paste, welche sich in Ammoniak mit blauvioletter, in Natronlauge mit grünblauer Farbe löst. Besonders charakteristisch sind die rein blaugrüne Farbe und das Absorptionsspectrum seiner Lösung in concentrirter Schwefelsäure. Beizen färbt es in blaueren bezw. grüneren Tönen an als das in der Patentschrift Nr. 661 53 beschriebene Pentacyanin. Durch Einwirkung von Ammoniak auf das neue Product erhält man einen neuen sehr schönen blaugrünen Farbstoff.In this way, it forms a dark purple paste, which turns blue-violet in ammonia and green-blue in sodium hydroxide solution solves. The purely blue-green color and the absorption spectrum are particularly characteristic its solution in concentrated sulfuric acid. Stain colors it in bluer respectively. greener ones Tones than the pentacyanine described in patent specification No. 661 53. By exposure ammonia on the new product gives a new, very beautiful blue-green one Dye.
Ersetzt man in obigem Beispiele die Salicylsäure durch die entsprechenden Mengen Phenol, Kresol, Resorcin, Hydrochinon, α- oder ß-Napthol, p-Oxybenzoe'säure, Kresolcarbonsäure oder Naphtolcarbonsäure, so erhält man Farbstoffe, welche ganz ähnliche Eigenschaften besitzen und Chrombeizen alle mehr oder weniger grünstichig blau anfärben.If one replaces the salicylic acid in the above example with the corresponding amounts of phenol, Cresol, resorcinol, hydroquinone, α- or ß-naphthol, p-oxybenzoic acid, cresol carboxylic acid or naphtholecarboxylic acid, dyes are obtained which have very similar properties and chrome stains color all more or less greenish blue.
Ganz genau wie das Chinon des Pentacyanins verhält sich auch das Chinon des »Hexacyanins« des Patentes Nr. 66153. Die vom Hexacyanin abstammenden Farbstoffe geben im allgemeinen etwas grünstichigere Nuancen als die entsprechenden Abkömmlinge des Pentacyanins. Desgleichen giebt das in der Patentschrift Nr. 68113 beschriebene Chinon aus dem Hexaoxyanthrachinon des Patentes Nr. 64418 mit Phenolen und Phenolcarbonsäuren Condensationsproducte, welche grofse Aehnlichkeit mit den Derivaten des Hexacyanins zeigen.The quinone of "hexacyanine" behaves exactly like the quinone of pentacyanine of Patent No. 66153. The dated Hexacyanine-derived dyes generally give slightly greener nuances than the corresponding derivatives of pentacyanine. The same applies to the patent specification No. 68113 from the hexaoxyanthraquinone of patent No. 64418 with phenols and phenolcarboxylic acids condensation products, which are very similar show with the derivatives of hexacyanine.
Die Eigenschaften aller dieser Farbstoffe ergeben sich aus folgender Tabelle:The properties of all these dyes are shown in the following table:
Farbstoff aus:Dye from:
Lösung
in Soda-Lösung solution
in soda solution
Lösung in Ammoniak Solution in ammonia
Lösung in Natronlauge Solution in caustic soda
Lösung in cone, chwefelsäure Solution in cone, sulfuric acid
Färbung auf Wolle vorgebeizt mit:Dyeing on wool pre-stained with:
Thonerde ChromAlumina chrome
Alizarinpentacyaninchinon + Phenol Alizarin pentacyanine quinone + phenol
+ ο - Kresol + ο - cresol
-t-p-Kresol. + Resorcin-t-p-cresol. + Resorcinol
Hydrochinon ,Hydroquinone,
+ o-Naphtol.. + ß-Naphtol . + Salicylsäure+ o-naphtol .. + ß-naphtol. + Salicylic acid
+ ρ-Oxybenzoesäure....+ ρ-oxybenzoic acid ....
+ ο - Kresotinsäure + ο - cresotinic acid
4- m-Kresotinsäure 4-m-cresotinic acid
17 18. 19 20. 2.1. 22. 2317 18. 19 20. 2.1. 22. 23
4- a-Naphtolcarbonsäure Alizarinhexacyaninchinon + Phenol 4- a-naphtholecarboxylic acid alizarinhexacyaninequinone + phenol
+ ο-Kresol + ο-cresol
+ ρ-Kresol + ρ-cresol
+ Resorcin + Resorcinol
+ Hydrochinon + Hydroquinone
+ a-Naphtol + a- naphtol
+ ß-Naphtol + ß-naphtol
+ Salicylsäure + Salicylic acid
+ ρ - Oxybenzoesäure + ρ - oxybenzoic acid
+ ο - KresotinsUure .... + m - Kresotinsäure+ ο - cresotinic acid .... + m - cresotinic acid
+ a-Naphtolcarbonsäure+ a-naphtholecarboxylic acid
dem Ghinon des Hexaoxyanthrachinons + Resorcin (Pat. Nr. 68113)the ghinone of hexaoxyanthraquinone + resorcinol (Pat. No. 68113)
SalicylsäureSalicylic acid
+ ρ - Oxybenzoesäure.... + Kresotinsäure + ρ - oxybenzoic acid .... + cresotinic acid
rothviolett red-violet
rothviolett red-violet
violettviolet
rothviolett red-violet
blauviolett blue-violet
violettviolet
blauviolett blue-violet
violettviolet
rothviolett red-violet
violett
braunrothviolet
brownish red
rothviolett red-violet
violettviolet
rothviolett red-violet
violettviolet
rothviolett red-violet
bläulichroth bluish red
schmutzig
blauviolett dirty
blue-violet
schmutzig
rothviolett
blaurothdirty
red-violet
bluish red
schmutzig
blaudirty
blue
violettviolet
rothviolett red-violet
violettviolet
rothviolett red-violet
violettblau violet blue
violettviolet
rothviolett red-violet
violettviolet
violettroth violet red
chmutzig violettdirty purple
rothviolett red-violet
violettviolet
braunviolett brown purple
rothviolett red-violet
violettviolet
blaublue
chmutzigdirty
violettviolet
blaublue
violettroth violet red
mifsfarbig mifs-colored
violettviolet
violettroth violet red
blaublue
blauviolett blue-violet
grünblaugreen Blue
violettviolet
blaublue
violettviolet
violettblau violet blue
chmutzig violettdirty purple
violettblau violet blue
ichmutzig blaudirty blue
chmutzig violettdirty purple
blauviolett blue-violet
violettviolet
grünlichblau greenish blue
violettviolet
grünlichblau greenish blue
reinblaupure blue
rothviolett red-violet
schmutzig blaudirty blue
grünblaugreen Blue
violettviolet
grüngreen
blau ;rünblaublue; green blue
blaublue
grün, Spectr.green, Spectr.
blaublue
grüngreen
röthlichblau reddish blue
grün ;rünblau . blaugreen; green blue. blue
violettviolet
violettblau violet blue
blauviolett blue-violet
violettblau violet blue
violettviolet
grünlichblau greenish blue
röthlichblau reddish blue
blaugrün blue green
blaublue
blaugrünblue green
blau blaugünblue blue green
grünlich· blaugreenish blue
blaublue
grüngreen
violett blaugrünviolet blue-green
blauviolett blue-violet
violettviolet
bläulichviolett blauviolett bluish violet blue violet
violettviolet
graublaugray-blue
blauviolett blue-violet
violettviolet
rothviolett red-violet
violettviolet
blaublue
;raublau blau; rough blue blue
grünlichblau greenish blue
graublaugray-blue
grünlichblau greenish blue
blaublue
grünlichblau greenish blue
;rünlich-■ blau; greenish ■ blue
grünblau blaugreen blue blue
grünlichblau greenish blue
blaublue
graublaugray-blue
violettblau violet blue
graublaugray-blue
Claims (1)
Die Ausführung des durch Anspruch i. geschützten Verfahrens unter Anwendung der im Patente No. 661 53 beschriebenen Chinone des Alizarinpentacyanins und des Alizarinhexacyanins. Process for the preparation of stain-coloring dyes of the alizarin series which contain polyoxyanthraquinone residues and phenol residues, characterized in that anthradichinones are combined with phenols.
The execution of the claim i. protected process using the patent no. 661 53 described quinones of alizarin pentacyanine and alizarin hexacyanine.
Die Ausführung des durch Anspruch 1. geschützten Verfahrens unter Anwendung des Chinons des isomeren Hexaoxyanthrachinons (Patent Nr. 68113) und folgender Phenole: Resorcin, Salicylsäure, p-Oxybenzoesäure oder Kresotinsäure.The execution of the process protected by claim 2 using phenol, o-cresol, p-cresol, resorcinol, hydroquinone, a-naphtol. ß-naphtol, salicylic acid, ρ - oxybenzoic acid, ο - or m - cresotinic acid, a - naphtholecarboxylic acid.
Carrying out the process protected by claim 1 using the quinone of the isomeric hexaoxyanthraquinone (Patent No. 68113) and the following phenols: resorcinol, salicylic acid, p-oxybenzoic acid or cresotinic acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE70234C true DE70234C (en) |
Family
ID=343629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT70234D Expired - Lifetime DE70234C (en) | Process for the preparation of stain-coloring dyes from anthradichinones and phenols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE70234C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6717182B1 (en) * | 1996-09-24 | 2004-04-06 | Nippon Sheet Glass Co., Ltd. | Edge-emitting light-emitting device having improved external luminous efficiency and self-scanning light-emitting device array comprising the same |
-
0
- DE DENDAT70234D patent/DE70234C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6717182B1 (en) * | 1996-09-24 | 2004-04-06 | Nippon Sheet Glass Co., Ltd. | Edge-emitting light-emitting device having improved external luminous efficiency and self-scanning light-emitting device array comprising the same |
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