CH224558A - Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. - Google Patents
Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series.Info
- Publication number
- CH224558A CH224558A CH224558DA CH224558A CH 224558 A CH224558 A CH 224558A CH 224558D A CH224558D A CH 224558DA CH 224558 A CH224558 A CH 224558A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid ester
- leuco
- sulfuric acid
- preparation
- weight
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 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 claims 2
- 150000004056 anthraquinones Chemical class 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 7
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 6
- 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 4
- 239000003795 chemical substances by application 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
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 sulfuric acid ester Chemical class 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- SZDVDUDLIIZMKX-UHFFFAOYSA-N copper;pyridine Chemical compound [Cu].C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 SZDVDUDLIIZMKX-UHFFFAOYSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
Ziusatzpatent zum Hauptpatent Nr. <B>222255.</B> Verfahren zur Herstellung des Leukosehwefelsäureesters eines Nftpenfarbstoffes der Inthrachinonreihe. Gegenstand dieses Patentes ist ein Ver fahren zur Herstellung des Leukoschwefel- säureestere eines Küpenfarbstoffes der An- tlirachinonreihe, welches darin besteht, dass man den Farbstoff,
der durch Kuppeln des diazotierten 1-Aminoanthrachinons mitAcet- essigsäure <B>- 5 -</B> clilor <B>-</B> 2<B>-</B> amino <B>-</B> 1.4<B>-</B> dim-ethoxy - benzol erhäItlipli ist, durch Behandlung mit einem reduzierenden Mittel und einem Schwefeltrioxyd liefernden. Veresterungs- mittel in Gegenwart einer tertiären Base, in den Leukoschwefelsäureester überführt.
Die Überführung des Küpenfarbstoff es in den Leukoschwefelsäureester erfolgt in der üblichen Weise, z. B. durch Behandeln des Farbstoffes in Gegenwart einer tertiken Base, wie z. B. Pyridin und eines Schwefel- trioxyd liefern-den Veresterungsmittels, wie z. B. Chlorsulionsäure oder Chlorsulfon- säureester, mit einem Metall, z.
B. mit Kup fer oder Eisen, Zur Aufarbeitung wird das Umsetzungs gemisch zweckmässig in eine Lösung von Natriumearbonat oder Natriumhydroxyd oder Ammoniak in Wasser gegeben, in ge eigneter Weise, z. B. durch Destillation im Vakuum von der tertiären, Base befreit und von den Metallsalzen abfiltriert. Aus dem Filtrat kann der gebildete Leukoseliwefel- säureester in Forin eines Salzes, z.
B. in Form des Natriumsalzes oder Kaliumsalzes durch Aussalzen mit Natrium-c'hlorid oder Kaliumehlo-rid gewonnen werden. Das aus gefällte Alkalimetallsalz des Leukoschwefel- säureesters wird abfiltriert und zur Er höhung der Haltbarkeit mit etwas Natrium- earbonat ersetzt.
<I>Beispiele:</I> <B>1.</B> In etwa<B>1000</B> Gewichtsteile Pyridin (Fraktion<B>125-126 ' G)</B> werden bei<B>15</B> bis 20'<B>C</B> 200 Gewichtsteile Chlorsulfonsäure zugetropft, dann werden<B>100</B> GewieUtsteile Kupferpulver und<B>100</B> Gewichtsteile des Farbstoffes ausdiazotiertem 1-Amino#anthra- chinon und Aoeteseigsäure-5-chlor-2-amino- 1.4-dimetlioxybenzoJ eingetragen.
Das Ge misch wird 2 Stunden bei 40'<B>C</B> verrührt, dann wird die Reaktionsmasse unter Rühren in<B>10 000</B> Gewichtsteile Wasser und<B>50</B> Ge wichtsteile Kieselgur gegeben. Man lässt einige Zeit absitzen und giesst dais Pyridin- wa,sser ab.
Das zurückbleibende Kupfer- Pyridin-Komplexsa,lz wird zweimal mit<B>je</B> <B>5000</B> Gewichtsteilen Wasser gewaschen und dann in einer Lösung von 240 Gewichts teilen Natronlauge 40' B6 in<B>9000</B> Ge wichtsteilen Wasser durch 1/-->.stündiges Rüh ren gelöst. Dae abgeschiedene Kupfersalz wird abgesaugt und gewaschen. Aus dem Filtrat wird der Leukoschwefelsäureester mit Natriumehlorid auegesalzen, abgesaugt und zur Reinigung nochmals umgelöst.
Der Leukoschwefel,säureester gibt auf Baumwolle, in der üblichen Weise mit sau ren Oxydationsmitteln entwickelt, ein leb haftes Orange von sehr guten Echtheits eigenschaften.
2. In ein Veresterungegemisch aus<B>800</B> Gewichtsteilen einer Pyridinfraktion vom Siedepunkt<B>125-126 ' C</B> und<B>150</B> Gewichts teilen Chlorsulfonsäure trägt man<B>60</B> Ge wichtsteile Eisenpulver und<B>100</B> Gewichts teile des Farbstoffes ein, der durch Kuppeln von diazotiertem 1-Aminoanthrachinon mit Aoetessig,sä,ure-5-chlor-2-amino,-l.4-dimeth- oxybenzol erhalten wird.
Das Reaätions- gemi.sch wird auf 40-50'<B>C</B> angeheizt und die Temperatur steigt infolge Reaktions- wärme kurze Zeit auf<B>60'</B> C. Nach Beendi gung der Veresterung wird die Reaktions masse in eine Lösung von<B>230</B> Gewichts teilen Natriumearbonat in 4000 Gewichts teilen Wasser gegeben und durch Vakuum destillation vom Pyridin befreit.
Die wäss- rige Lösung wird vom Eieenschlamm durch Filtration getrennt und der gebildete Schwefelsäureester aus dem Filtrat mit Na- triumehlorid ausgfflalzen,. Der ausgesalzene Eeter wird abgesaugt und mit Natriumear- bonat haltbar gemacht. Er ist identisch mit der im Beispiel<B>1</B> beschriebenen Verbindung.
Additional patent to main patent no. <B> 222255. </B> Process for the preparation of the leucosulfuric acid ester of a pen dye of the inthraquinone series. The subject of this patent is a process for the production of the leuco-sulfuric acid ester of a vat dye of the anti-quinone series, which consists in the dye,
that by coupling the diazotized 1-aminoanthraquinone with acetoacetic acid <B> - 5 - </B> clilor <B> - </B> 2 <B> - </B> amino <B> - </B> 1.4 < B> - </B> dim-ethoxy - benzene is obtainable by treatment with a reducing agent and a sulfur trioxide. Esterifying agent in the presence of a tertiary base, converted into the leuco sulfuric acid ester.
The conversion of the vat dye into the leuco sulfuric acid ester takes place in the usual manner, for. B. by treating the dye in the presence of a tertiary base, such as. B. pyridine and a sulfur trioxide supply-the esterifying agent such. B. chlorosulionic acid or chlorosulfonic acid ester, with a metal, z.
B. with Kup fer or iron, for work-up, the reaction mixture is expediently given in a solution of sodium carbonate or sodium hydroxide or ammonia in water, in a suitable manner, for. B. freed from the tertiary base by distillation in vacuo and the metal salts are filtered off. The leukoselulfuric acid ester formed can be converted from the filtrate in the form of a salt, e.g.
B. in the form of the sodium salt or potassium salt by salting out with sodium chloride or potassium chloride. The precipitated alkali metal salt of the leuco sulfuric acid ester is filtered off and replaced with a little sodium carbonate to increase the shelf life.
<I> Examples: </I> <B> 1. </B> About <B> 1000 </B> parts by weight of pyridine (fraction <B> 125-126 'G) </B> are used in <B> 15 to 20 parts by weight of chlorosulfonic acid are added dropwise, then 100 parts by weight of copper powder and 100 parts by weight of the dye are diazotized 1-amino anthraquinone and aoeteseigsäure-5-chloro-2-amino-1,4-dimetlioxybenzoJ entered.
The mixture is stirred for 2 hours at 40 ° C., then the reaction mass is added to 10,000 parts by weight of water and 50 parts by weight of kieselguhr with stirring . It is allowed to sit for a while and the pyridine water is poured off.
The remaining copper-pyridine complex salt is washed twice with <B> each </B> <B> 5000 </B> parts by weight of water and then in a solution of 240 parts by weight of sodium hydroxide solution 40 'B6 in <B> 9000 < / B> parts by weight of water dissolved by stirring for 1 / ->. Hour. The deposited copper salt is filtered off with suction and washed. The leuco-sulfuric acid ester from the filtrate is salted with sodium chloride, filtered off with suction and redissolved again for cleaning.
The leuco sulfur acid ester gives cotton, developed in the usual way with acidic oxidizing agents, a lively orange with very good fastness properties.
2. An esterification mixture of <B> 800 </B> parts by weight of a pyridine fraction with a boiling point of <B> 125-126 'C </B> and <B> 150 </B> parts by weight of chlorosulfonic acid is <B> 60 < / B> parts by weight of iron powder and <B> 100 </B> parts by weight of the dye, which is obtained by coupling diazotized 1-aminoanthraquinone with acetic acid, acidic, 5-chloro-2-amino, -l.4-dimeth - oxybenzene is obtained.
The reaction mixture is heated to 40-50 ° C and the temperature rises to 60 ° C for a short time as a result of the heat of reaction. After the esterification has ended, the Reaction mass is poured into a solution of <B> 230 </B> parts by weight of sodium carbonate in 4000 parts by weight of water and the pyridine is removed by vacuum distillation.
The aqueous solution is separated from the iron sludge by filtration and the sulfuric acid ester formed is flattened out of the filtrate with sodium chloride. The salted-out Eeter is sucked off and made durable with sodium carbonate. It is identical to the connection described in example <B> 1 </B>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE224558X | 1940-04-13 | ||
| CH222255T | 1941-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224558A true CH224558A (en) | 1942-11-30 |
Family
ID=25726624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224558D CH224558A (en) | 1940-04-13 | 1941-02-28 | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224558A (en) |
-
1941
- 1941-02-28 CH CH224558D patent/CH224558A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH222255A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| DE724273C (en) | Process for the preparation of leuco-sulfuric acid esters of anthraquinone-azo dyes | |
| DE729301C (en) | Process for the preparation of leuco-sulfuric acid esters of anthraquinone-azo dyes | |
| CH226630A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH224562A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| DE659883C (en) | Process for the preparation of a new dioxypyrene | |
| CH224556A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH224561A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH224559A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH224560A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH321742A (en) | Process for the preparation of an azo dye | |
| CH226638A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH292664A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH224557A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH329257A (en) | Process for the preparation of a metal-containing azo dye | |
| CH226633A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH224555A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH224554A (en) | Process for the preparation of the leuco-sulfuric acid ester of a vat dye of the anthraquinone series. | |
| CH292668A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH293616A (en) | Process for the preparation of a leuco-sulfuric acid ester salt of an anthraquinone-azo dye. | |
| CH310690A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH305960A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH306376A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH292659A (en) | Process for the preparation of a metal-containing azo dye. | |
| CH321741A (en) | Process for the preparation of an azo dye |