DE255078C - - Google Patents
Info
- Publication number
- DE255078C DE255078C DENDAT255078D DE255078DA DE255078C DE 255078 C DE255078 C DE 255078C DE NDAT255078 D DENDAT255078 D DE NDAT255078D DE 255078D A DE255078D A DE 255078DA DE 255078 C DE255078 C DE 255078C
- Authority
- DE
- Germany
- Prior art keywords
- water
- ice
- mixture
- required amount
- dyes
- 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.)
- Active
Links
- 239000000987 azo dye Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- -1 aromatic diazo compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 210000002268 Wool Anatomy 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2H-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- BHKWXQBWGLKDKU-UHFFFAOYSA-N 3-(aminodiazenyl)benzene-1,2-disulfonic acid Chemical compound NN=NC1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O BHKWXQBWGLKDKU-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N Chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 241000588733 Pseudescherichia vulneris Species 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N Sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229940034107 Sulfazine Drugs 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N Thioacetic acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical class OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 255078 -.. KLASSE 22 a. GRUPPE 1.- M 255078 - .. CLASS 22 a. GROUP 1.
Dr. MAXCLAASZ in DANZIG-LANGFUHR. Verfahren zur Herstellung von Azo farbstoffen. Patentiert im Deutschen Reiche vom 13. Januar 1912 ab.Dr. MAXCLAASZ in DANZIG-LANGFUHR. Process for the production of azo dyes. Patented in the German Empire on January 13, 1912.
Benzothiazine der AtomkonfigurationBenzothiazines of the atomic configuration
C NC N
CSCS
bilden sich in glatter Reaktion durch Kondensation von Orthonitrothiophenolen mit Monochloressigsäure und darauf folgender Reduktion »form in smooth reaction by condensation of orthonitrothiophenols with monochloroacetic acid and subsequent reduction »
3535
4040
NHNH
-NO9 -NO 9
-S · CH2- COOH-S · CH 2 - COOH
-CO -CH9 -CO -CH 9
5555
Dieselbe Laktambildung erfolgt durch Reduktion auch dann, wenn Thioessigsäuren zu Sulfoessigsäuren oxydiert werden, wodurch dann am Schwefel oxydierte Benzothiazine, soge-25 nannte Sulfazone, entstehen. .The same lactam formation takes place through reduction even when thioacetic acids are added Sulfoacetic acids are oxidized, as a result of which benzothiazines, so-called-25, are then oxidized on the sulfur called sulfazones. .
r-NO.r-NO.
-SO2-CH2-COOH-SO 2 -CH 2 -COOH
NH I NH I
r-COr-CO
-CH2 SO9.-CH 2 SO 9 .
6060
6565
Der gleiche Reaktionsverlauf tritt auch bei kernsubstituierten Orthonitrothiophenolen, 45 z.B. bei 2·4-Dinitrothiophenol, ein, wodurch dann kernsubstituierte Sulfazone erhalten werden.The same course of reaction also occurs with ring-substituted orthonitrothiophenols, 45 e.g. with 2 · 4-dinitrothiophenol, whereby ring-substituted sulfazones are then obtained.
NO2-S^y-NO2 NO 2 -S ^ y-NO 2
III.III.
NH2-NH 2 -
-S-CH9-COOH-S-CH 9 -COOH
IV.IV.
NH9-NH 9 -
CH9-COOHCH 9 -COOH
So gewonnene Sulfazone kuppeln mit Diazoniumsalzen zu Farbstoffen, die Seide und Wolle, zum Teil auch Baumwolle, Substantiv leuchtend und lichtecht färben.Sulfazones obtained in this way combine with diazonium salts to form dyes, silk and To dye wool, sometimes also cotton, nouns bright and lightfast.
Beispiel ι.Example ι.
Die eisgekühlte Lösung von 223 g i-Naphtylamin-5-sulfosäure, der erforderlichen Menge Alkali und 70 g Natriumnitrit in 3 1 Wasser wird in eine eisgekühlte Mischung von 150 g konzentrierter Schwefelsäure und 1 1 Wasser eingerührt. Nach einiger Zeit wird die Mischung in eine Lösung von 200 g Sulfazin (Formel II) und der erforderlichen Menge Alkali in 2 1 Wasser eingerührt. Der Farbstoff wird ausgesalzen und getrocknet. Er färbt Wolle gelb.The ice-cold solution of 223 g of i-naphthylamine-5-sulfonic acid, the required amount of alkali and 70 g of sodium nitrite in 3 l of water is poured into an ice-cold mixture of 150 g concentrated sulfuric acid and 1 1 water. After a while the mixture will in a solution of 200 g sulfazine (formula II) and the required amount of alkali in 2 1 Stir in water. The dye is salted out and dried. He dyes wool yellow.
Die eisgekühlte Lösung von 35 g Aminoazobenzoldisulfosäure, der erforderlichen Menge Soda und y.g Natriumnitrit in 2 1 Wasser wird in eine eisgekühlte Mischung von 55 g Salzsäure (spez. Gew. 1,19) und 0,5 1 Wasser eingerührt. Nach mehreren Stunden wird die Mischung in eine Lösung von 20 g SulfazonThe ice-cold solution of 35 g of aminoazobenzene disulfonic acid, the required amount of soda and yg sodium nitrite in 2 l of water is stirred into an ice-cold mixture of 55 g of hydrochloric acid (specific weight 1.19) and 0.5 l of water. After several hours, the mixture is dissolved in a solution of 20 g of sulfazone
(Formel II) und der erforderlichen Menge Alkali in 200 ecm Wasser eingetragen. Der Farbstoff wird ausgesalzen und getrocknet.· Er färbt Wolle rötlichorange.(Formula II) and the required amount of alkali in 200 ecm of water. Of the Dye is salted out and dried. It dyes wool reddish orange.
Die eisgekühlte Lösung von 2,4 g 2 ·8-Aminonaphtol-6-sulfosäure, der erforderlichen Menge Soda und 0,7 g Natriumnitrit in 100 ecm Wasser wird in eine eisgekühlte Mischung von 1,5 g konzentrierter Schwefelsäure und 20 g Wasser eingerührt.The ice-cold solution of 2.4 g of 2x8-aminonaphthol-6-sulfonic acid, the required amount of soda and 0.7 g of sodium nitrite in 100 ecm of water is in an ice-cold mixture of 1.5 g of concentrated sulfuric acid and 20 g of water stirred in.
Nach einiger Zeit wird diese Mischung in eine alkalische Löung von 2 g Sulfazon (Formel II) in 25 ecm Wasser hineingegossen. Der Farbstoff wird ausgesalzen und getrocknet. Er färbt Baumwolle braun.After a while this mixture is in an alkaline solution of 2 g of sulfazone (Formula II) poured into 25 ecm of water. The dye is salted out and dried. He dyes cotton brown.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE255078C true DE255078C (en) |
Family
ID=513208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT255078D Active DE255078C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE255078C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE940483C (en) * | 1952-12-04 | 1956-03-22 | Bayer Ag | Process for the preparation of metal complex-forming azo dyes |
| US4960870A (en) * | 1987-02-11 | 1990-10-02 | Ciba-Geigy Corporation | Heavy metal complex azo dyes containing a benzothiophene-1,1-dioxide, 2,1-benzothiazine-2,2-dioxide, 1,4-benzothiazine-1,1-dioxide or thienopyridine-1,1-dioxide coupling component |
-
0
- DE DENDAT255078D patent/DE255078C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE940483C (en) * | 1952-12-04 | 1956-03-22 | Bayer Ag | Process for the preparation of metal complex-forming azo dyes |
| US4960870A (en) * | 1987-02-11 | 1990-10-02 | Ciba-Geigy Corporation | Heavy metal complex azo dyes containing a benzothiophene-1,1-dioxide, 2,1-benzothiazine-2,2-dioxide, 1,4-benzothiazine-1,1-dioxide or thienopyridine-1,1-dioxide coupling component |
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