CH249123A - Process for the preparation of a stable, water-soluble leuco-sulfuric acid ester salt of a vat dye of the anthraquinone series. - Google Patents
Process for the preparation of a stable, water-soluble leuco-sulfuric acid ester salt of a vat dye of the anthraquinone series.Info
- Publication number
- CH249123A CH249123A CH249123DA CH249123A CH 249123 A CH249123 A CH 249123A CH 249123D A CH249123D A CH 249123DA CH 249123 A CH249123 A CH 249123A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- acid ester
- stable
- sulfuric acid
- soluble
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 5
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- -1 sulfuric acid ester salt Chemical class 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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
- C09B9/00—Esters or ester-salts of leuco compounds of vat dyestuffs
- C09B9/02—Esters or ester-salts of leuco compounds of vat dyestuffs of anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines beständigen, wasserlöslichen Leukoschwefelsäureester- salzes eines Küpenfarbstoffes der Anthrachinonreihe: Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines be ständigen, wasserlöslichen Leukoschwefel- säureestersalzes eines Küpenfarbstoffes der Anthraehinonreihe, we@Iahes darin besteht,
da.ss man den durch Kuppeln von diazotiertem 1.-Aminoanth@ra,ehinon mit 1-p-Phenyl-ben- zoyl-acetylamino-2,5-di.chlorbenzol der For mel
EMI0001.0020
erhältlichen Farbstoff durch Befiandeln mit einem reduzierenden Mittel und einem Schwe- feltrioxyd liefernden Veresterungsmittel in Gegenwart einer tertiären Base in den sauren Leul#:
osch-,vefelsäuree.ster überführt und den selben in das beständige, wasserlösliche Na triumsalz umwandelt.
Die Überführung des Küpenfarbstoffes in .den Leukoschwefelsäure@ester kann in der Weise geschehen, dass man z. B. den Farb stoff durch ein Reduktionsmittel, das, wobt die Chinongruppe, nicht aber die Azogruppe reduziert, in die Leukover,bin@dung verwan delt und diese mit einer Schwefeltrioxyd lie- fernden Substanz, wie z. B. Chlorsulfonsäure, in Gegenwart einer tertiären Base, wie z. B. Pyridin, verestert.
<I>Beispiel:</I> Ein V eresterungsgemisch, das,durch Zu tropfen von<B>15</B> g Chlorsulfonsäure in 75 g Pyridin vom Sdp. 125-128 C erhalten wird, versetzt man mit 10 g Farbstoff, der durch Kuppeln von diazotiertem 1-Aminoanthra- chinon mit 1-p-Phenyl-benzoylacetylamino- ?,5-,dichlorbenzol erhalten wird, und ver mischt mit 6 g Eisenpulver.
Nach .mehrstün digem Verrühren bei 50 C wird das Ver- esterungsgemisch in eine Lösung von 25 g Natriumearbonat in 1,0,0,0 b Wasser einge tragen und das Pyridin Im Vakuum abdestil- liert. Man filtriert vom Eisensehlamm ab und salzt den Ester mit NatriumAlorid aus.
Das so ausgesalz.ene Leukos@e hwefeläuree3ter- salz wird abgesaugt und :durch Zugabe von wenig Natronlauge verpastet.
Das neue Leukos.chwefels.äureestersalz ist in Wasser unter Bildung einer orangenen Lösung löslich und liefert. durch geeignete Oxydation einen gelben Küpenfarbstoff. Nach den für diese Farbstoffklasse üblichen Entwicklungsverfahren wird auf ,der Faser ein volles Gelb mit sehr guten Echtheitseigen- sehaften erhalten. Das LeukosaUvv.efelsäure- esters:alz besitzt eine ausgezeichnete Affini tät zur pflanzlichen Faser.
Process for the production of a stable, water-soluble leuco-sulfuric acid ester salt of a vat dye of the anthraquinone series: The subject matter of the present invention is a process for the production of a permanent, water-soluble leuco-sulfuric acid ester salt of a vat dye of the anthraquinone series, which consists in
da.ss one obtained by coupling diazotized 1.-Aminoanth @ ra, ehinon with 1-p-phenyl-benzoyl-acetylamino-2,5-di-chlorobenzene of the formula
EMI0001.0020
dye obtainable by treating with a reducing agent and an esterifying agent which provides sulfur trioxide in the presence of a tertiary base in the acidic Leul #:
osch-, vefelsäuree.ster and converts the same into the permanent, water-soluble sodium salt.
The conversion of the vat dye in .den leucosulfuric acid @ ester can be done in such a way that one z. B. the dye by a reducing agent, which, wovt the quinone group, but not the azo group, is transformed into the leukover, bind @ delt and these with a sulfur trioxide delivering substance, such as. B. chlorosulfonic acid, in the presence of a tertiary base, such as. B. pyridine, esterified.
<I> Example: </I> An esterification mixture, which is obtained by dropping <B> 15 </B> g of chlorosulfonic acid in 75 g of pyridine with a boiling point of 125-128 C, is mixed with 10 g of dye, obtained by coupling diazotized 1-aminoanthraquinone with 1-p-phenyl-benzoylacetylamino-?, 5-, dichlorobenzene, and mixed it with 6 g of iron powder.
After several hours of stirring at 50 ° C., the esterification mixture is introduced into a solution of 25 g of sodium carbonate in 1.0, 0, 0 g of water and the pyridine is distilled off in vacuo. The iron flour is filtered off and the ester is salted out with sodium chloride.
The salted out leukosulfur acid salt is sucked off and: pasted by adding a little sodium hydroxide solution.
The new Leukos.chulfuric acid ester salt is soluble in water to form an orange solution and provides. a yellow vat dye by suitable oxidation. Following the development processes customary for this class of dyes, a full yellow with very good fastness properties is obtained on the fiber. The LeukosaUvv.efelsäure- ester: alz has an excellent affinity for vegetable fibers.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH249123T | 1945-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH249123A true CH249123A (en) | 1947-06-15 |
Family
ID=4467328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH249123D CH249123A (en) | 1945-07-28 | 1945-07-28 | Process for the preparation of a stable, water-soluble leuco-sulfuric acid ester salt of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH249123A (en) |
-
1945
- 1945-07-28 CH CH249123D patent/CH249123A/en unknown
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