CH481173A - Process for the preparation of anthraquinone disperse dyes - Google Patents
Process for the preparation of anthraquinone disperse dyesInfo
- Publication number
- CH481173A CH481173A CH692467A CH692467A CH481173A CH 481173 A CH481173 A CH 481173A CH 692467 A CH692467 A CH 692467A CH 692467 A CH692467 A CH 692467A CH 481173 A CH481173 A CH 481173A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- preparation
- formula
- disperse dyes
- optionally substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000986 disperse dye Substances 0.000 title description 3
- 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 title description 2
- 150000004056 anthraquinones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000975 dye Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- SXYRTDICSOVQNZ-UHFFFAOYSA-N 1-(2-methoxyethoxy)ethanol Chemical compound COCCOC(C)O SXYRTDICSOVQNZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HTHKZOCCOVYKKI-UHFFFAOYSA-N dinaphthalen-1-ylmethanedisulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)O)S(O)(=O)=O)=CC=CC2=C1 HTHKZOCCOVYKKI-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols 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
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Anthrachinon-Dispersionsfarbstoffen Es wurde gefunden; dass man ausgezeichnete Dispersionsfarbstoffe der Formel
EMI0001.0007
worin R, ein Wasserstoffatom oder einen gegebenenfalls substituierten Alkylrest mit 1 bis 4 Kohlenstoffatomen, R2 ein Wasserstoff- oder Halogenatom,
eine Hydroxyl- gruppe oder einen gegebenenfalls substituierten Alkyl- oder Alkoxyrest, R3 ein Wasserstoffatom oder einen gegebenenfalls substituierten Alkylrest und, n eine ganze Zahl von 2 bis einschliesslich 6 bedeutet, erhält,
wenn man eine Verbindung der Formel
EMI0001.0036
mit einer Verbindung der Formel R30-(CH.-),-OH (III) umsetzt.
Als Substituenten an den Alkyl@ und Alkoxyresten kommen insbesondere Halogenatome, Cyan-, Thiol- oder Hydroxylgruppen, gegebenenfalls auch weitere Alkoxy- reste und Aryloxyreste in Betracht. Halogen bedeutet vorzugsweise Chlor oder Brom.
Als Substituenen ausgeschlossen sind Carbonsäune- oder Sulfonsäurereste. Die Umsetzung findet vorzugsweise in einem über schuss der Verbindung der Formel (11I) unter Zusatz eines alkalischen Kondensationsmittels, z. B. Natrium- oder Kaliumhydroxid, bei Temperaturen zwischen 100 und 180 C statt.
Als Verbindungen der Formel (III) kommen z. B. in Betracht: 'A'thylenglykol, Propylenglykol, Diäthylengly- kol oder Mothoxyäthoxyäthanol.
Die Herstellung von Verbindungen der Formel (II) ist allgemein bekannt und z. B. in den deutschen Patent schriften Nrn. 445 296 und 446 563 beschrieben.
Die erfindungsgemäss hergestellten Farbstoffe eignen sich nach Zerkleinerung, die in Gegenwart von Disper- gier- und/oder Füllmitteln erfolgen kann, hervorragend zum Färben, Klotzen oder Bedrucken von Formkörpern aus vollsynthetischen oder halbsynthetischen, hydro- phoben,hochmolekularen organischen Stoffen.
Solche Stoffe sind insbesondere Fasern, Fäden, Vliese, Gewebe oder Gewirke aus linearen Polyestern:, Cellulose-2i/- acetat oder Cel#lulosetniacetat. Gefärbt, geklotzt bzw. be druckt wird nach allgemein bekannten Verfahren, dabei erhält man Färbungen bzw. Drucke mit guten AlZgemein- echtheiten.
Die in den Beispielen genannten Teile sind Gewichts- teile, die Temperaturen sind in Celsiusgraden angegeben. <I>Beispiel 1</I> In 180 Teilen Methoxyäthoxyäthanol werden 10 Teile Kaliumhydroxyd und 25 Teile des Natriumsalzes der 3-Hydroxyphenyl-4,8-diaminoanthrarufin- 6-sulfosäure bei 145 etwa 10 Stunden gerührt, bis sich kein Aus gangsmaterial mehr nachweisen lässt.
Es wird nun auf 800 Teile Wasser gegossen, mit 20 Teilen Natrium- bicarbonat ausgefällt, abfiltriert, mit Wasser gewaschen und getrocknet. Der erhaltene Farbstoff löst sich in Chlorbenzol mit rotstichigblauer Farbe.
<I>Beispiel 2</I> In 150 Teilen Diäthylenglykol werden 10 Teile Kaliumhydroxyd und 25 Teile des Natriumsalzes der 3-Methoxyphenyl-4,8-diaminoanthrarufin@ 6-sulfosäure 5 Stunden bei 130 gerührt, hierauf auf 600 Teile Wasser gegossen und wie in Beispiel 1 aufgearbeitet. Der Farbstoff löst sich in Chlorbenzol mit rotstichig- blauer Farbe und färbt Polyesterfasern rotstichigblau an.
<I>Beispiel 3</I> In 150 Teilen Äthylenglykol werden 10 Teile Kaliumhydroxyd und 25 Teile des Natriumsalzes der 3-Hydroxyphenyl-4,8-diaminoanthrarufin 6-sulfosäure 20 Stunden bei 135 gerührt und hierauf wie in Bei- spiel 1 aufgearbeitet. Es wird ein Farbstoff erhalten, der Polyesterfasern rotstichigblau anfärbt.
<I>Färbevorschrift</I> 7 Teile des nach Beispiel 1 erhaltenen Farbstoffes werden mit 4 Teilen dinaphthylmethandisulfonsaurem Natrium, 4 Teilen Natriumcetylsulfat und 5 Teilen wasserfreiem Natriumsulfat in einer Kugelmühle während 48 Stunden zu einem feinen Pulver gemahlen.
3,5 Teile des so erhaltenen Färbepräparates werden mit wenig Wasser angeteigt und die erhaltene Suspension sodann durch ein Sieb einem 2 Teile Natriumlaurylsulfat in 4000 Teen Wasser enthaltenden Färbebad zugesetzt. Das Flottenverhältnis beträgt hier 1 : 40, es kann jedoch innerhalb weiter Grenzen verändert werden.
Man gibt <B>100</B> Teile gereinigtes Polyesterfasermaterial Dacron (eingetragene Marke) bei 40 bis 50 in das Bad, fügt 20 Teile einer Emulsion eines chlorierten Benzols in Wasser zu, erwärmt das Bad langsam auf 100 und färbt während 1 bis 2 Stunden bei 95 bis 100 . Das rotstichigblau gefärbte Färbegut wird hierauf gespült, geseift, erneut gespült und dann: getrocknet.
Process for the preparation of anthraquinone disperse dyes It has been found; that you can get excellent disperse dyes of the formula
EMI0001.0007
wherein R, a hydrogen atom or an optionally substituted alkyl radical having 1 to 4 carbon atoms, R2 is a hydrogen or halogen atom,
a hydroxyl group or an optionally substituted alkyl or alkoxy group, R3 is a hydrogen atom or an optionally substituted alkyl group and n is an integer from 2 to 6 inclusive,
when you have a compound of the formula
EMI0001.0036
with a compound of the formula R30- (CH .-), - OH (III).
Particularly suitable substituents on the alkyl and alkoxy radicals are halogen atoms, cyano, thiol or hydroxyl groups, and optionally also further alkoxy radicals and aryloxy radicals. Halogen is preferably chlorine or bromine.
Carboxylic acid or sulfonic acid residues are excluded as substituents. The reaction takes place preferably in an excess of the compound of formula (11I) with the addition of an alkaline condensing agent, eg. B. sodium or potassium hydroxide, at temperatures between 100 and 180 C instead.
As compounds of the formula (III), for. B. into consideration: 'ethylene glycol, propylene glycol, diethylene glycol or mothoxyethoxyethanol.
The preparation of compounds of the formula (II) is generally known and, for. B. in the German patent writings nos. 445 296 and 446 563 described.
The dyes prepared according to the invention are, after comminution, which can be carried out in the presence of dispersants and / or fillers, outstandingly suitable for dyeing, padding or printing molded articles made of fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances.
Such materials are in particular fibers, threads, fleeces, woven or knitted fabrics made of linear polyesters: cellulose acetate or cellulose acetate. Dyeing, padding or printing is carried out according to generally known processes, and dyeings or prints with good general properties are obtained.
The parts mentioned in the examples are parts by weight and the temperatures are given in degrees Celsius. <I> Example 1 </I> 10 parts of potassium hydroxide and 25 parts of the sodium salt of 3-hydroxyphenyl-4,8-diaminoanthrarufin-6-sulfonic acid are stirred in 180 parts of methoxyethoxyethanol for about 10 hours until no more starting material can be detected leaves.
It is then poured into 800 parts of water, precipitated with 20 parts of sodium bicarbonate, filtered off, washed with water and dried. The dye obtained dissolves in chlorobenzene with a reddish blue color.
<I> Example 2 </I> 10 parts of potassium hydroxide and 25 parts of the sodium salt of 3-methoxyphenyl-4,8-diaminoanthrarufin @ 6-sulfonic acid are stirred in 150 parts of diethylene glycol for 5 hours at 130, then poured onto 600 parts of water and how worked up in Example 1. The dye dissolves in chlorobenzene with a reddish-blue color and stains polyester fibers in a reddish-blue.
Example 3 10 parts of potassium hydroxide and 25 parts of the sodium salt of 3-hydroxyphenyl-4,8-diaminoanthrarufin 6-sulfonic acid are stirred in 150 parts of ethylene glycol for 20 hours at 135 and then worked up as in Example 1. A dye is obtained which dyes polyester fibers in a reddish blue.
<I> Dyeing instructions </I> 7 parts of the dye obtained according to Example 1 are ground with 4 parts of sodium dinaphthylmethanedisulfonic acid, 4 parts of sodium cetyl sulfate and 5 parts of anhydrous sodium sulfate in a ball mill for 48 hours to a fine powder.
3.5 parts of the dye preparation thus obtained are made into a paste with a little water and the suspension obtained is then added through a sieve to a dyebath containing 2 parts of sodium lauryl sulfate in 4000 teen water. The liquor ratio here is 1:40, but it can be changed within wide limits.
100 parts of cleaned polyester fiber material Dacron (registered trademark) are added to the bath at 40 to 50, 20 parts of an emulsion of a chlorinated benzene in water are added, the bath is slowly heated to 100 and colored for 1 to 2 Hours at 95 to 100. The reddish blue dyed material is then rinsed, soaped, rinsed again and then: dried.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH692467A CH481173A (en) | 1967-05-17 | 1967-05-17 | Process for the preparation of anthraquinone disperse dyes |
| BE699802D BE699802A (en) | 1967-05-17 | 1967-06-12 | |
| FR110138A FR1526748A (en) | 1967-05-17 | 1967-06-13 | Anthraquinone dispersion dyes, their manufacturing process and applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH692467A CH481173A (en) | 1967-05-17 | 1967-05-17 | Process for the preparation of anthraquinone disperse dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH481173A true CH481173A (en) | 1969-11-15 |
Family
ID=4317189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH692467A CH481173A (en) | 1967-05-17 | 1967-05-17 | Process for the preparation of anthraquinone disperse dyes |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE699802A (en) |
| CH (1) | CH481173A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093367A3 (en) * | 1982-05-03 | 1986-08-27 | Bayer Ag | Anthraquinone dyes, their preparation and use, and a dichroic material containing these anthraquinone dyes |
-
1967
- 1967-05-17 CH CH692467A patent/CH481173A/en not_active IP Right Cessation
- 1967-06-12 BE BE699802D patent/BE699802A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093367A3 (en) * | 1982-05-03 | 1986-08-27 | Bayer Ag | Anthraquinone dyes, their preparation and use, and a dichroic material containing these anthraquinone dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| BE699802A (en) | 1967-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |