CH205067A - Process for the preparation of an anthraquinone dye. - Google Patents
Process for the preparation of an anthraquinone dye.Info
- Publication number
- CH205067A CH205067A CH205067DA CH205067A CH 205067 A CH205067 A CH 205067A CH 205067D A CH205067D A CH 205067DA CH 205067 A CH205067 A CH 205067A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dodecylaniline
- phenol
- anthraquinone
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000001000 anthraquinone dye Substances 0.000 title description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 7
- -1 dodecylaniline anthraquinone Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- SOANRMMGFPUDDF-UHFFFAOYSA-N 2-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=CC=C1N SOANRMMGFPUDDF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/547—Anthraquinones with aromatic ether groups
-
- 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 199189. Verfahren zur Herstellung eines Anthraehinonfarbstoffes. Im Hauptpatent ist ein Verfahren zur Herstellung eines neuen Anthraähinonfarb- stoffes, nämlich 1-Amino-4-p-dodecylanilin- 2-phenoxyanthrachinondisulfosäure beschrie ben.
Gemäss vorliegender Erfindung stellt man denselben Anthrachinonfarbstoff her, in dem man Phenol auf eine 2-Halogen-l-amino- 4--do,d,ecylanilinanthraohinonsulfo@säure, wie sie erhalten werden kann durch Sulfonieren von 2 Halogen-l-amino-4-p-dodecylanilinan- thrachinon mit schwachem Oleum, einwirken lässt und die erhaltene Verbindung sulfoniert.
Als 2-Halogen-l-amino-@4-p-@dod.ecylanilin- anthrachinons@ulfosäure kann 2-Brom-l-amino- 4-p-,dodecylanilinanthrachinozisulfosäure zur Anwendung kommen.
Die Behandlung mit dem Phenol kann zweckmässigerwei.se dureh Erhitzen mit einem Alkalimetallsalz des Phenols in über schüssigem Phenol geschehen. Die Sulfonie- run"o" lässtsich zweckmässigerweise durch Lösen in 100%iger Schwefelsäure und Zusetzen von Oleum ausführen.
Der Farbstoff ist eine violettblaue Sub stanz, welche sich in konzentrierter Schwefel säure mit rötlichvioletter Farbe löst: Mit Wasser gibt sie klare blaue Lösungen, die leicht schäumen. Der Farbstoff färbt Wolle in lebhaft rötlichblauen Tönen, die sehr gute Walk- und Lichtechtheit aufw.ei@s-en und in tensivem Waschen sehr gut widerstehen.
<I>Beispiel;</I> Man erhitzt zusammen während 61 Stun den auf 170-175' C 70 Teile 2-Brom.-l- amino - 4 - p -,dod-ecylanilinanthrachinonsulfo- säure (als Natriumsalz), wie sie erhältlich ist durch Sulfonieren von 2, Brom-l=amino-4-p- .dodecylanilinanthrachinon (verigl. Beispiel 1 der brit. Patentschrift 443776)
mit schwa chem Oleum, 10 Teile gepulvertes Ätznatron und 3'50 Teile Phenol. Das Reaktions.gemis.ch wird bei #80' C in 2:50 Teile 5%ige Natron- lauge gegossen, die ausgefällte Phenoxyver- bindung abfiltriert, mit kaltem Wasser ge waschen und bei 80-100 C getrocknet.
50 Teile der so erhaltenen 1-Amino-4-p- dodecylanilin - 2: - phenoxyanthrachinonmono- sulfosäure löst man bei 15-20 C in 500 Teilen 100%iger Schwefelsäure und fügt 10 Teile 20%iges .Oleum hinzu. Nach einigen Minuten wird das Sulfonierungsgemiseh in 2000 Teile Eiswasser gegossen, das Produkt abfiltriert und der - Filterkuchen in 3000 Teilen Wasser mit Soda neutralisiert.
Hierauf wird der Farbstoff bei<B>70</B> C mit 3,00 Teilen Kochsalz ausgefällt, abfiltriert und bei 80 C getrocknet.
Additional patent to main patent no. 199189. Process for the production of an anthraquinone dye. The main patent describes a process for the production of a new anthraquinone dye, namely 1-amino-4-p-dodecylaniline-2-phenoxyanthraquinone disulfonic acid.
According to the present invention, the same anthraquinone dye is prepared by adding phenol to a 2-halo-1-amino-4-do, d, ecylanilinanthraohinonsulfo @ acid, such as can be obtained by sulfonating 2 halo-1-amino-4 -p-dodecylanilinanthrachinon with weak oleum, allowed to act and sulfonated the compound obtained.
The 2-halo-1-amino- @ 4-p- @ dod.ecylaniline-anthraquinonic @ sulfonic acid used can be 2-bromo-1-amino-4-p-, dodecylaniline anthraquinocisulfonic acid.
The treatment with the phenol can expediently take place by heating with an alkali metal salt of the phenol in excess phenol. The sulfonic run "o" can conveniently be carried out by dissolving it in 100% sulfuric acid and adding oleum.
The dye is a violet-blue substance that dissolves in concentrated sulfuric acid with a reddish-violet color: With water, it gives clear blue solutions that easily foam. The dye dyes wool in vivid reddish blue tones, which are very good boiled and lightfastness onw.ei@s-en and withstand intensive washing very well.
<I> Example; </I> They are heated together for 61 hours at 170-175 ° C, 70 parts of 2-bromo-1-amino-4-p-, dod-ecylaniline anthraquinonesulphonic acid (as the sodium salt) as they are can be obtained by sulfonating 2, bromine-1 = amino-4-p- .dodecylaniline anthraquinone (verigl. Example 1 of British Patent 443776)
with weak oleum, 10 parts of powdered caustic soda and 3'50 parts of phenol. The reaction.gemis.ch is poured into 2:50 parts of 5% sodium hydroxide solution at 80.degree. C., the precipitated phenoxy compound is filtered off, washed with cold water and dried at 80-100.degree.
50 parts of the 1-amino-4-p-dodecylaniline-2: -phenoxyanthraquinone monosulfonic acid thus obtained are dissolved in 500 parts of 100% sulfuric acid at 15-20 ° C. and 10 parts of 20% iges oleum are added. After a few minutes, the sulfonation mixture is poured into 2000 parts of ice water, the product is filtered off and the filter cake is neutralized in 3000 parts of water with soda.
The dye is then precipitated at 70 ° C with 3.00 parts of sodium chloride, filtered off and dried at 80 ° C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB205067X | 1936-07-01 | ||
| CH199189T | 1937-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205067A true CH205067A (en) | 1939-05-31 |
Family
ID=25723230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205067D CH205067A (en) | 1936-07-01 | 1937-06-14 | Process for the preparation of an anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205067A (en) |
-
1937
- 1937-06-14 CH CH205067D patent/CH205067A/en unknown
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