DE528607C - Process for the production of chromium-containing dyes - Google Patents
Process for the production of chromium-containing dyesInfo
- Publication number
- DE528607C DE528607C DE1930528607D DE528607DD DE528607C DE 528607 C DE528607 C DE 528607C DE 1930528607 D DE1930528607 D DE 1930528607D DE 528607D D DE528607D D DE 528607DD DE 528607 C DE528607 C DE 528607C
- Authority
- DE
- Germany
- Prior art keywords
- chromium
- production
- acid
- parts
- 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.)
- Expired
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 8
- 229910052804 chromium Inorganic materials 0.000 title claims description 7
- 239000011651 chromium Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 title description 9
- 239000000987 azo dye Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 6
- 239000010985 leather Substances 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229940114055 beta-resorcylic acid Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- UJRBOEBOIXOEQK-UHFFFAOYSA-N oxo(oxochromiooxy)chromium hydrate Chemical compound O.O=[Cr]O[Cr]=O UJRBOEBOIXOEQK-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004532 chromating Methods 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
- C09B45/40—Chromium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von chromhaltigen Farbstoffen Es wurde gefunden, daß man wertvolle chromhaltige Farbstoffe erhält, wenn man die I aus dianotierten sulfonierten Aminen, die keine Hydroxylgruppe enthalten, und ß-Resorcylsäurc erhältlichen Azofarbstoffe mit chromabgebenden Mitteln behandelt. Die Chromierung der Farbstoffe kann beispielsweise durch Erhitzen auf dem Wasserbad oder durch Kochen mit Lösungen von Chromsalzen, z. B. Chromformiat. -acetat, -fluor id usw., durchgeführt «-erden. Die erhaltenen chromhaltigen Farbstoffe geben besonders auf Leder schöne, volle, gleichmäßige Braunfärbungen von guter Lichtechtheit.Process for the production of chromium-containing dyes It has been found that valuable chromium-containing dyes are obtained if the I from dianotized sulfonated amines that do not contain a hydroxyl group, and ß-resorcylic acid Azo dyes treated with chromium donating agents. The chromating of the dyes can for example by heating on a water bath or by boiling with solutions of chromium salts, e.g. B. chromium formate. -acetate, -fluoride, etc., carried out «-erden. The chromium-containing dyes obtained give beautiful, full, uniform brown colorations with good lightfastness.
Beispiel i 38 C#,e@viclit-;teile des Azofarbstoffes aus dianotierter \Ietanilsiiure-> ß-Resorcylsäure ;-erden mit etwa 5oo Teilen Wasser und .4o Teilen einer 27"1, Cr,0, enthaltenden Chromoxydhvdratpaste und 21 Teilen 85prozentiger Ameisensäure unter Rückfluß etwa i Stunde gekocht und eingedampft. Man erhält ein braunes Pulver, das Leder in sehr schönem gelbbraunem Ton lichtecht anfärbt und ein gutes Egalisiervermögen auf Chromleder besitzt.Example i 38 C #, e @ viclit-; parts of the azo dye from dianotated acetanilic acid> β-resorcylic acid Ground with about 500 parts of water and .40 parts of a 27 "1, Cr, 0, containing chromium oxide hydrate paste and 21 parts of 85 percent formic acid under reflux for about 1 hour and evaporated. A brown powder is obtained, the leather in a very beautiful yellow-brown tone dyes lightfast and has good leveling properties on chrome leather.
Die auf gleiche Weise aus dem entsprechenden Sulfanilsäurefarbstoff hergestellte komplexe Chromverbindung färbt Leder mit ähnlichen Eigenschaften nur etwas roter an. Beispiel z 42 Gewichtsteile des Azofarbstoties aus dianotierter Naphthionsäure und ß-Resorcylsäure werden wie in Beispiel i chromiert und mit festem Kochsalz ausgesalzen und getrocknet. Man erhält einen Farbstoff, der Leder echt braun anfärbt. In ähnlicher `.'eise können auch andere Farbstoffe aus anderen dianotierten Naplithylaminsulfonsiiuren und Resorcy-lsäure hergestellt werden.The same way from the corresponding sulfanilic acid dye The complex chromium compound produced only stains leather with similar properties a little redder. Example z 42 parts by weight of the azo dye from dianotized Naphthionic acid and ß-resorcylic acid are chromed as in Example i and with solid Salted out table salt and dried. A dye is obtained that makes the leather real stains brown. In a similar way, other dyes can also be dianotized from other Naplithylamine sulfonic acids and resorcyclic acid are produced.
An Stelle von Chromformiat können auch andere Chromsalze, wie Chromacetat, Chromfluorid u. dgl., verwendet werden.Instead of chromium formate, other chromium salts such as chromium acetate, Chromium fluoride and the like can be used.
Beispiel 3 39 Gewichtsteile des Azofarbstoffes aus dianotierter Aminoazobenzolsulfonsäure und Resorcvlsäure werden in etwa 8oo Teilen Wasser und qo Teilen einer etwa 25 °/" Cr@O,; haltigen Chromoxydhydratpaste und 2o Teflen 85prozentiger Ameisensäure i bis 2 Stunden gekocht und dann ausgesalzen. Man erhält einen Farbstoff, der Leder satt rot anfärbt und gut lichtecht ist.EXAMPLE 3 39 parts by weight of the azo dye from dianotized aminoazobenzenesulfonic acid and resorcvic acid are boiled in about 800 parts of water and qo parts of a chromium oxide hydrate paste containing about 25 % Cr @ O, and 20 parts of 85% formic acid for 1 to 2 hours and then salted out Dye that gives leather a deep red color and is lightfast.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE528607T | 1930-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE528607C true DE528607C (en) | 1931-07-01 |
Family
ID=6553747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930528607D Expired DE528607C (en) | 1930-05-01 | 1930-05-01 | Process for the production of chromium-containing dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE528607C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060167A (en) * | 1958-01-17 | 1962-10-23 | Durand & Huguenin Ag | Process for the manufacture of new metallizable 4-hydroxy-5-carboxyphenyl-2:2'-dihydroxy-azo-dyestuffs |
-
1930
- 1930-05-01 DE DE1930528607D patent/DE528607C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060167A (en) * | 1958-01-17 | 1962-10-23 | Durand & Huguenin Ag | Process for the manufacture of new metallizable 4-hydroxy-5-carboxyphenyl-2:2'-dihydroxy-azo-dyestuffs |
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