DE243087C - - Google Patents
Info
- Publication number
- DE243087C DE243087C DE1907243087D DE243087DA DE243087C DE 243087 C DE243087 C DE 243087C DE 1907243087 D DE1907243087 D DE 1907243087D DE 243087D A DE243087D A DE 243087DA DE 243087 C DE243087 C DE 243087C
- Authority
- DE
- Germany
- Prior art keywords
- red
- violet
- acid
- arylthioglycolic
- toluidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- XENVCRGQTABGKY-ZHACJKMWSA-N Chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- -1 nitro hydrocarbon Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 241000490025 Schefflera digitata Species 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 8
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-o-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 5
- DADSZOFTIIETSV-UHFFFAOYSA-N N,N-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000984 vat dye Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 150000004992 toluidines Chemical class 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 2-Nitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ILCQYORZHHFLNL-UHFFFAOYSA-N N-bromoaniline Chemical compound BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-Xylidine Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- KRXWWBIFQYPEAD-UHFFFAOYSA-N COC1=C(N)C=CC=C1.[Cl] Chemical compound COC1=C(N)C=CC=C1.[Cl] KRXWWBIFQYPEAD-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- ODJZWXPPPDTYPH-UHFFFAOYSA-N N,N-dichloro-3-methylaniline Chemical compound CC1=CC=CC(N(Cl)Cl)=C1 ODJZWXPPPDTYPH-UHFFFAOYSA-N 0.000 description 1
- SOGVTRYSTYAVRT-UHFFFAOYSA-N N-bromo-2-methylaniline Chemical compound CC1=CC=CC=C1NBr SOGVTRYSTYAVRT-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N N-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001419 dependent Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 150000003460 sulfonic acids 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
- C09B7/00—Indigoid dyes
- C09B7/10—Bis-thionapthene indigos
Description
^ ft^ ft
"Κ 1V"Κ 1 V
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- ΛΙ 243087 KLASSE 22 e. GRUPPE- ΛΙ 243087 CLASS 22 e. GROUP
KALLE &CO. AKT-GES. in BIEBRICH a. Rh. Verfahren zur Herstellung von Küpenfarbstoffen.KALLE & CO. ACT-TOTAL in BIEBRICH a. Rh. Process for the production of vat dyes.
Zusatz zum Patent 241910 vom 20. März 1907.Addendum to patent 241910 of March 20, 1907.
Patentiert im Deutschen Reiche vom 24. August 1907 ab. Längste Dauer: 19. März 1922.Patented in the German Empire on August 24, 1907. Longest duration: March 19, 1922.
Nach dem Verfahren des Hauptpatents 241910 werden Arylthioglycolsäuren mit einer freien Ortho- oder Peristellung mit Hilfe von Schwefelsäurechlorhydrin (Chlorsulfonsäure) in unsulfierte Küpenfarbstoffe übergeführt. Es zeigte sich dabei, daß die Ausbeuten an Küpenfarbstoffen wesentlich von der Temperatur, Schnelligkeit'des Eintragens, Gesamtdauer der Einwirkung abhängig sind.According to the method of the main patent 241910 arylthioglycolic acids with a free ortho- or peristaltion with the help of sulfuric acid chlorohydrin (chlorosulfonic acid) in unsulfated vat dyes transferred. It was found that the yields of vat dyes essentially depends on the temperature, speed of entry, total duration are dependent on the action.
Es wurde nun gefunden, daß in vielen Fällen der Zusatz von Nitrokohlenwasserstoffen die Einhaltung der für die Ausbeute günstigsten Temperatur und Einwirkungsdauer erleichtert.It has now been found that in many cases the addition of nitrohydrocarbons compliance with the most favorable temperature and exposure time for the yield relieved.
Dieses Ergebnis war nicht vorauszusehen, weil die Chlorsulfonsäure auf die Nitrokohlenwasserstoffe chlorierend oder sulforierend hätte einwirken und demnach den Verlauf der Reaktion hätte in Frage stellen können. Letzteres ist nun nicht der Fall; vielmehr löst sich das Schwefelsäurechlorhydrin z. B. in Chlornitrobenzol, Nitrobenzol, Dinitrochlorbenzol usw. unter nur schwacher Erwärmung auf. Trägt man nun in diese Lösung eine Arylthioglycolsäure, z. B. ψ-Cumylthioglycolsäure, ein, so erhält man nach dem Eingießen auf Eis und Abtrennen des Nitrokörpers den unsulfurierten Küpenfarbstoff. Dasselbe tritt ein, wenn die Arylthioglycolsäuren in aromatischen Nitrokohlenwasserstoffen gelöst und mit Chlorsulfonsäure versetzt werden.This result could not have been foreseen because the chlorosulfonic acid reacts to the nitro hydrocarbons chlorinating or sulphating would have had an effect and therefore the course of the reaction could have questioned. The latter is now not the case; rather, that dissolves Sulfuric acid chlorohydrin e.g. B. in chloronitrobenzene, nitrobenzene, dinitrochlorobenzene, etc. under only weak heating. If you now carry an arylthioglycolic acid into this solution, z. B. ψ-cumylthioglycolic acid, so after pouring onto ice and separating off the nitro body, the unsulfurized one is obtained Vat dye. The same thing occurs when the arylthioglycolic acids in aromatic nitrohydrocarbons dissolved and mixed with chlorosulfonic acid.
ι Teil der substituierten Arylthioglycolsäure (z. B. derjenigen aus p-Chlor-o-toluidin, asymmetrischem Xylidin, ψ-Cumidin usw.) wird unter Kühlung in eine Mischung von 2 Volumteilen Nitrobenzol oder Chlornitrobenzol usw. und 2 Volumteilen Chlorsulfonsäure eingetragen. Nachdem die Salzsäureentwicklung vorüber ist, wird auf Eis gegossen und der Nitrokörper durch Wasserdampfdestillation oder andere bekannte Hilfsmittel abgetrennt. Der zurückbleibende Farbstoff wird mit verdünntem Alkali, sodann mit Alkohol gewaschen.ι Part of the substituted arylthioglycolic acid (e.g. that from p-chloro-o-toluidine, asymmetric Xylidine, ψ-cumidine, etc.) is cooled into a mixture of 2 parts by volume Nitrobenzene or chloronitrobenzene etc. and 2 parts by volume of chlorosulfonic acid entered. After the development of hydrochloric acid has passed, it is poured onto ice and the nitro body separated by steam distillation or other known auxiliaries. The remaining dye is diluted with Alkali, then washed with alcohol.
Die so erhaltenen Farbstoffe sind keine Sulfosäuren, sie lassen sich vielmehr in alkalischer Lösung mit Hydrosulfit verküpen und färben je nach der angewandten Arylthioglycolsäure in verschiedenen Nuancen, wie aus nachstehender Tabelle hervorgeht.The dyes obtained in this way are not sulfonic acids, they can be more alkaline Vat the solution with hydrosulfite and color depending on the arylthioglycolic acid used in different nuances, as shown in the table below.
Chloranilin (NH2: Cl = 1: 4) auf Baumwolle violettrotChloraniline (NH 2 : Cl = 1: 4) on cotton violet-red
Chloranilin (NH2: Cl = 1: 3) . . - - rotChloroaniline (NH 2 : Cl = 1: 3). . - - Red
Chloranilin (NH2: Cl = 1: 2) - - rotChloroaniline (NH 2 : Cl = 1: 2) - - red
6060
Dichloranilin (NH2 Dichloroaniline (NH 2
Dichloranilin (N H~2 Dichloroaniline (NH ~ 2
Dichloranilin (NH2 Dichloroaniline (NH 2
Dichloranilin (NH2 Dichloroaniline (NH 2
Cl: Cl — τ: 2: 4)Cl: Cl - τ: 2: 4)
Cl: Cl = ι
Cl: Cl~x
Cl: Cl = ι Cl: Cl = ι
Cl: Cl ~ x Cl: Cl = ι
3:4; -3: 4; -
3:5; auf Wolle weinrot3: 5; burgundy on wool
auf Baumwolle rotviolett rotviolett bläulichroton cotton red-violet red-violet bluish-red
Toluidin (N H2: C Hs = 1: 4) auf Baumwolle bläulichrotToluidine (NH 2 : CH s = 1: 4) on cotton bluish red
Toluidin (NH2: CH3 = 1:2) -Toluidine (NH 2 : CH 3 = 1: 2) -
Toluidin (NH2: CH3 = 1:3) -Toluidine (NH 2 : CH 3 = 1: 3) -
Chlortoluidin (NH2)CH3: Cl = 1:2: 4) Chlorotoluidine (NH 2 ) CH 3 : Cl = 1: 2: 4)
Chlortoluidin (NH2: CH3: Cl = 1:3:4;Chlorotoluidine (NH 2 : CH 3 : Cl = 1: 3: 4;
Chlortoluidin (NH2: CH3: Cl = 1: 4: 6) Chlorotoluidine (NH 2 : CH 3 : Cl = 1: 4: 6)
Chlortoluidin (NH2: CH3: Cl = 1: 4 : 5;Chlorotoluidine (NH 2 : CH 3 : Cl = 1: 4: 5;
Bromtoluidin (NH2: CH3: Br = 1:2:4; Bromotoluidine (NH 2 : CH 3 : Br = 1: 2: 4;
Bromanilin (NH2: Br = 1:4) Bromoaniline (NH 2 : Br = 1: 4)
Bromanilin (NH2: Br = 1: 3) Bromoaniline (NH 2 : Br = 1: 3)
m-Xylidin (NH2: CH3: CH3 = 1:2:4; m-xylidine (NH 2 : CH 3 : CH 3 = 1: 2: 4;
ψ-Cumidin (N H2: C H3: CHZ:CH3 — 1:2:4:5; ■."... ψ-Cumidine (NH 2 : CH 3 : CH Z : CH 3 - 1: 2: 4: 5; ■. "...
Chlor-p-xylidin (NH2: CH3: Cl: CH3 = 1:2: 4: 5) Chloro-p-xylidine (NH 2 : CH 3 : Cl: CH 3 = 1: 2: 4: 5)
Dichlor-m-toluidin (NH2: Cl: Cl: CH3 = τ: 2: 4: 5) .... Dichloro-m-toluidine (NH 2 : Cl: Cl: CH 3 = τ: 2: 4: 5) ....
Nitranilin (NH2: NO2 = 1: 2) Nitraniline (NH 2 : NO 2 = 1: 2)
Anisidin (NH2: OC H3 — 1: 3; Anisidine (NH 2 : OC H 3-1 : 3;
Phenetidin (NH2: OC2H5 = 1:3; Phenetidine (NH 2 : OC 2 H 5 = 1: 3;
a-Naphtylamin (N H2 = x) a-naphthylamine (NH 2 = x)
,8-Naphtylamin (NH2 — 2) , 8-naphthylamine (NH 2 - 2)
Dichlor-a-naphtylamin (NH2: Cl: Cl = τ: 2: 4) Dichloro-a-naphthylamine (NH 2 : Cl: Cl = τ: 2: 4)
Chlor-o-anisidin (N H2: O C H3: Cl = 1:2:5) Chlorine-o-anisidine (NH 2 : OCH 3 : Cl = 1: 2: 5)
Acet-m-phenylendiamin (NH2: NHC2H3O == 1:3; bläulichrot rotAcet-m-phenylenediamine (NH 2 : NHC 2 H 3 O == 1: 3; bluish red
rotviolett rotviolett rot violett rotviolettred-violet red-violet red violet red-violet
rotviolettred-violet
rotviolett violettstichig rotred-violet violet-tinged red
violettviolet
violettblauviolet blue
rotviolettred-violet
rotviolettred-violet
grünblaugreen Blue
gelbrotyellow Red
gelbrotyellow Red
blaugraublue-gray
braunBrown
blaugraublue-gray
blauviolettblue-violet
braun.Brown.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT55883D AT55883B (en) | 1907-08-23 | 1909-03-27 | Process for the production of vat dyes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE243087C true DE243087C (en) |
Family
ID=502240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907243087D Expired - Lifetime DE243087C (en) | 1907-08-23 | 1907-08-23 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE243087C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101061A2 (en) * | 1982-08-13 | 1984-02-22 | Hoechst Aktiengesellschaft | Preparation process of an organic pigment on the basis of 4,4',7,7'-tetrachlorothioindigo |
-
1907
- 1907-08-23 DE DE1907243087D patent/DE243087C/de not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101061A2 (en) * | 1982-08-13 | 1984-02-22 | Hoechst Aktiengesellschaft | Preparation process of an organic pigment on the basis of 4,4',7,7'-tetrachlorothioindigo |
| EP0101061A3 (en) * | 1982-08-13 | 1985-11-27 | Hoechst Aktiengesellschaft | Preparation process of an organic pigment on the basis of 4,4',7,7'-tetrachlorothioindigo |
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