CH186846A - Process for the preparation of 1,4-diamino-2-p-isoamylphenoxy-3-isoamylmercaptoanthraquinone sulfonic acid. - Google Patents
Process for the preparation of 1,4-diamino-2-p-isoamylphenoxy-3-isoamylmercaptoanthraquinone sulfonic acid.Info
- Publication number
- CH186846A CH186846A CH186846DA CH186846A CH 186846 A CH186846 A CH 186846A CH 186846D A CH186846D A CH 186846DA CH 186846 A CH186846 A CH 186846A
- Authority
- CH
- Switzerland
- Prior art keywords
- product
- reacted
- isoamyl
- diaminoanthraquinone
- reaction product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- -1 1,4-diamino-2-p-isoamylphenoxy-3-isoamylmercaptoanthraquinone sulfonic acid Chemical compound 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003513 alkali Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- YSNKZJBCZRIRQO-UHFFFAOYSA-N 4-Isopentylphenol Chemical compound CC(C)CCC1=CC=C(O)C=C1 YSNKZJBCZRIRQO-UHFFFAOYSA-N 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 238000009963 fulling Methods 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 8
- 239000000047 product Substances 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000975 dye Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- KZYAYVSWIPZDKL-UHFFFAOYSA-N 1,4-diamino-2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(Cl)C(Cl)=C2N KZYAYVSWIPZDKL-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- VCLVUNFJTOOMIR-UHFFFAOYSA-M sodium;acetyl sulfate Chemical compound [Na+].CC(=O)OS([O-])(=O)=O VCLVUNFJTOOMIR-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 1,4-IDiamino-2-p-isoamylphenogy-3-isoamylmerkapto- anthraehinonsulfosäure. Gegenstand der Erfindung ist ein Ver fahren zur lIerstellung von 1,4-Diamino-2-p- isoamylphenoxy- 3 -isoam.ylmerkapto- anthra- chinonsulfosäure, gemäss', welchem man ein 2,3-Dihalogen-1,4-diaminoanthrachinon, ein Alkalisulfid,
p - Isoamylphenol und ein Isoamylhalogenid aufeinander einwirken lässt und das so erhaltene Produkt sulfiert. Man kann die genannten Verbindungen in beliebiger Reihenfolge aufeinander einwirken lassen. Als Alkalisulfid kann ein Alkali monosulfid oder Alkalidisulfid verwendet werden.
Die Behandlung mit p-Isoamylphenol kann durch Erhitzen in Gegenwart von Alkali stattfinden. Das Sulfonieren kann durch Auflösen des 1:4-Diamino-2-p-iso- amylphenoxy - 3 - isoamylmercaptoanthrachi- nons in konzentrierter Schwefelsäure und durch Zusatz von Oleum bewirkt werden.
1 : 4-Diamino- 2-p -isoamylphenoxy-3 - iso- amylmercaptoanthrachinonsulfosäure ist ein neues Produkt. Sie ist ein violettes Pulver, das sich in Wasser mit violetter Farbe löst. Sie färbt Wolle und andere animalische Fasern aus einem neutralen oder leicht sau ren Bad, vorzugsweise mit dem Zusatz eines Hilfsfärbemittels, wie Natriumacetylsulfat oder Glaubersalz, in hellvioletten Tönen. von guter Festigkeit gegen strenges Waschen, Walken und Licht.
Beispiel <I>Z:</I> 200 Teile Natrium-2-chlor-1 :4-diamino- 3 - mercaptoanthrachinon, hergestellt durch Behandeln von 2,3-Dichlor-1,4-diamino-an- thrachinon in siedendem Äthylalkohol mit einem Überschuss von Natriumdisulfid (NazSz), Abtreiben des Alkohols mit Dampf und Ausfällen des Salzes,<B>8'00</B> Teile Alkohol und 90 Teile Isoamylbromid werden eine halbe Stunde lang bei 75 C zusammen ge- rührt.
Das Produkt wird kalt gefiltert, nach einander mit Alkohol und Wasser gewaschen und bei<B>50'</B> C getrocknet.
100 Teile des Produktes, 300 Teile p-Iso- amylphenol und 30 -\Teile Natriumhydrogyd- pulver werden in einem geschlossenen Ge fäss bei 175 C 6 Stunden lang gerührt, auf <B>90'</B> C abgekühlt, das Gemisch in 3380 Teile 3%ige Natronlauge eingegossen und das suspendierte violette Produkt gefiltert, mit Wasser gut gewaschen und bei 50 C ge trocknet.
100 Teile des Produktes werden unter Umrühren in 1000 Teilen 100%iger Schwe felsäure bei 15 bis<B>20</B> C aufgelöst, 150 Teile Oleum (2-0% reines S03) werden zu gesetzt und die Temperatur für eine halbe Stunde auf 20 bis 25 C gehalten, bis Probe portionen. zeigen, dass die Sulfonierung voll ständig ist. Das Gemisch wird dann in<B>3</B>500 Teile Eiswasser laufen gelassen und der ge fällte Farbstoff gefiltert. Er wird bei<B>70'</B> C in 5000 Teile Wasser eingerührt, mit Na triumkarbonat neutralisiert und mit Salz ge fällt.
Das Produkt bildet ein violettes Pul ver, welches mit heissem Wasser leicht leb haftviolette, schaumige Lösungen gibt. Wolle wird in neutralem oder schwach saurem Bade in violetten, strengem Waschen, Wal ken und Licht sehr gut widerstehenden Tönen gefärbt.
<I>Beispiel 2:</I> 30 Teile 2, : 3-Dichlor-1 : 4-@diaminoan- thrachinon, 10'0 Teile p-Isoamylphenol und 6 Teile Ätznatron werden .6 Stunden lang bei 175 C zusammen gerührt.
Das Reaktions gemisch wird in 500 Teile Wasser und 300 Teile Ätznatron geschüttet, kalt gefiltert, mit Wasser gewaschen und bei 40' C ge trocknet. .30 Teile des Produktes, 150 Teile Alkohol und 30 Teile einer 25 %igen, wässe rigen Lösung von Natriumdisulfid werden umgeriihrt und 2 Stunden lang gekocht. Das Gemisch wird von allen suspendierten Teilen abfiltriert, mit 400 Teilen Wasser verdünnt und das Produkt .durch Zusatz von Chlor wasserstoffsäure gefällt.
Es wird gefiltert, mit Wasser gewaschen, in 50 Teilen Pyridin aufgelöst und durch Zusatz von 15 Teilen Isoamylbromid bei 9:5 C während einer Stunde alkyliert. Das Produkt wird kalt gefiltert und mit Alkohol gewaschen und dann getrocknet.
Es wird dann wie in Beispiel 1 sulfo- niert und ergibt dasselbe Produkt.
Process for the preparation of 1,4-IDiamino-2-p-isoamylphenogy-3-isoamylmercapto-anthraquinone sulfonic acid. The invention relates to a process for the production of 1,4-diamino-2-p-isoamylphenoxy-3-isoam.ylmercapto-anthraquinone sulfonic acid, according to which a 2,3-dihalo-1,4-diaminoanthraquinone, an alkali sulfide,
Allowing p - isoamylphenol and an isoamyl halide to act on one another and sulfate the product thus obtained. The compounds mentioned can be allowed to act on one another in any order. As the alkali sulfide, an alkali monosulfide or alkali disulfide can be used.
The treatment with p-isoamylphenol can take place by heating in the presence of alkali. The sulfonation can be brought about by dissolving the 1: 4-diamino-2-p-iso-amylphenoxy - 3 - isoamylmercaptoanthraquinone in concentrated sulfuric acid and by adding oleum.
1: 4-Diamino-2-p -isoamylphenoxy-3-iso-amylmercaptoanthraquinone sulfonic acid is a new product. It is a purple powder that dissolves in water with a purple color. It dyes wool and other animal fibers from a neutral or slightly acidic bath, preferably with the addition of an auxiliary dye such as sodium acetyl sulfate or Glauber's salt, in light purple shades. of good resistance to severe washing, fulling and light.
Example <I> Z: </I> 200 parts of sodium 2-chloro-1: 4-diamino-3-mercaptoanthraquinone, prepared by treating 2,3-dichloro-1,4-diamino-anthraquinone in boiling ethyl alcohol with an excess of sodium disulfide (NazSz), driving off the alcohol with steam and precipitating the salt, <B> 8'00 </B> parts of alcohol and 90 parts of isoamyl bromide are stirred together at 75 ° C. for half an hour.
The product is filtered cold, washed successively with alcohol and water and dried at <B> 50 '</B> C.
100 parts of the product, 300 parts of p-isoamylphenol and 30 parts of sodium hydrogen powder are stirred in a closed vessel at 175 ° C. for 6 hours, cooled to 90 ° C., the mixture in 3380 parts of 3% sodium hydroxide solution are poured in and the suspended violet product is filtered, washed well with water and dried at 50.degree.
100 parts of the product are dissolved with stirring in 1000 parts of 100% sulfuric acid at 15 to 20 C, 150 parts of oleum (2-0% pure SO3) are added and the temperature is maintained for half an hour Maintained at 20 to 25 C until sample portions. show that the sulfonation is complete. The mixture is then run into 3 500 parts of ice water and the precipitated dye is filtered. It is stirred into 5000 parts of water at 70 ° C, neutralized with sodium carbonate and precipitated with salt.
The product forms a purple powder which, when mixed with hot water, gives slightly vivid purple, foamy solutions. Wool is dyed in a neutral or weakly acidic bath in violet, severe washing, fulling and light-resistant tones.
<I> Example 2: </I> 30 parts of 2: 3-dichloro-1: 4- @ diaminoanthrachinone, 10'0 parts of p-isoamylphenol and 6 parts of caustic soda are stirred together at 175 ° C. for 6 hours.
The reaction mixture is poured into 500 parts of water and 300 parts of caustic soda, filtered cold, washed with water and dried at 40 'C. 30 parts of the product, 150 parts of alcohol and 30 parts of a 25% strength aqueous solution of sodium disulphide are stirred and boiled for 2 hours. The mixture is filtered off from all suspended parts, diluted with 400 parts of water and the product .by adding hydrochloric acid precipitated.
It is filtered, washed with water, dissolved in 50 parts of pyridine and alkylated by adding 15 parts of isoamyl bromide at 9: 5 C for one hour. The product is filtered cold and washed with alcohol and then dried.
It is then sulphonated as in Example 1 and gives the same product.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB186846X | 1934-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH186846A true CH186846A (en) | 1936-10-15 |
Family
ID=10116642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH186846D CH186846A (en) | 1934-11-14 | 1935-11-14 | Process for the preparation of 1,4-diamino-2-p-isoamylphenoxy-3-isoamylmercaptoanthraquinone sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH186846A (en) |
-
1935
- 1935-11-14 CH CH186846D patent/CH186846A/en unknown
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