DE289030C - - Google Patents
Info
- Publication number
- DE289030C DE289030C DENDAT289030D DE289030DA DE289030C DE 289030 C DE289030 C DE 289030C DE NDAT289030 D DENDAT289030 D DE NDAT289030D DE 289030D A DE289030D A DE 289030DA DE 289030 C DE289030 C DE 289030C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acids
- dyes
- combined
- acid esters
- naphtol
- 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
- 150000003460 sulfonic acids Chemical class 0.000 claims description 6
- -1 disazo diazo compounds Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000975 dye Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-Aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 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
- 239000000987 azo dye Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/062—Phenols
- C09B31/065—Phenols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/068—Naphthols
- C09B31/072—Naphthols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHEIMPERIAL
PATENTAMT.PATENT OFFICE.
Zusatz zum Patent 286091.Addendum to patent 286091.
Durch das Hauptpatent 286091 ist ein Verfahren geschützt, nach welchem die Arylsulfosäureester von p- und m-Aminophenolen zum Aufbau von waschechten Azofarbstoffen für Wolle verwendet werden. Es wurde nun weiter gefunden, daß man ebenfalls zu walkechten Wollfarbstoffen gelangt, wenn man die sekundären Disazofarbstoffe herstellt, welche als Anfangskomponente die Arylsulfosäureester von Aminonaphtolen bzw. deren Sulfosäuren, in Mittelstellung Amine der Naphtalin- oder Benzolreihe oder deren Sulfosäuren und als Endkomponente β-Naphtol bzw. dessen Derivate enthalten.The main patent 286091 protects a process according to which the aryl sulfonic acid esters of p- and m-aminophenols for the construction of washable azo dyes for Wool can be used. It has now been found that one can also whip-proof Wool dyes gets when one makes the secondary disazo dyes, which as Initial component the aryl sulfonic acid esters of aminonaphthols or their sulfonic acids, in Middle position amines of the naphthalene or benzene series or their sulfonic acids and as the end component Contain β-naphtol or its derivatives.
Nach dem Verfahren der Patentschrift 202116 wurden zwar bereits die Arylsulfosäureester von i-Amino-8-oxynaphtalinsulfosäuren zur Herstellung von sekundären Disazofarbstoffen verwendet, welche in Endstellung 2-Amino-5-oxynaphtalin-7-sulf osäure bzw. deren Derivate enthalten. Diese Farbstoffe, welche bei diesem Verfahren als Zwischenprodukte hergestellt werden, eignen sich jedoch nicht zur Verwendung als' walkechte Wollfarbstoffe, da sie beim Walken mitverwobene Baumwolle stark anfärben.According to the process of patent specification 202116, the aryl sulfonic acid esters were already of i-amino-8-oxynaphthalene sulfonic acids for the production of secondary disazo dyes used, which in the end position 2-amino-5-oxynaphthalene-7-sulf oic acid or their Derivatives included. These dyes, which are used as intermediates in this process are produced, but are not suitable for use as' non-milled wool dyes, because they stain interwoven cotton heavily during fulling.
Die Darstellung der Farbstoffe erfolgt in der für sekundäre Disazofarbstoffe gebräuchlichen Weise.The dyes are represented in the manner customary for secondary disazo dyes Way.
47,5 kg des p-Toluolsulfoesters der i-Amino-8-oxynaphtalin-3 · 6-disulfosäure werden mit 70 kg Salzsäure und 6,9 kg Natriumnitrit diazotiert. Der Diazokörper wird hierauf mit 15 kg α - Naphtylamin in salzsaurer Lösung vereinigt und unter allmählicher Zugabe von Natriumacetat so lange gerührt, bis die Kombination beendet ist. Man macht hierauf alkalisch, setzt 9 kg Natriumnitrit hinzu und säuert mit überschüssiger Salzsäure an. Nach mehrstündigem Rühren wird der braungefärbte Diazokörper ausgesalzen, abfiltriert und hierauf mit 14,5 kg ß-Naphtol, welches mit Wasser in 12 kg Natronlauge von 40 ° Be und 20 kg Soda gelöst wurde, gekuppelt. Der Farbstoff wird zur vollständigen Fällung ausgesalzen, filtriert, gepreßt und getrocknet. Er färbt Wolle walkecht und Seide wasserecht blauviolett. 47.5 kg of the p-toluenesulfoester of i-amino-8-oxynaphthalene-3 · 6-disulfonic acid are diazotized with 70 kg of hydrochloric acid and 6.9 kg of sodium nitrite. The diazo body is then combined with 15 kg of α-naphthylamine in a hydrochloric acid solution and stirred with the gradual addition of sodium acetate until the combination is finished. It is then made alkaline, 9 kg of sodium nitrite are added and the mixture is acidified with excess hydrochloric acid. To stirring for several hours, the brown-colored diazo body is salted out, filtered off and then with 14.5 kg ß-naphtol, which with water was dissolved in 12 kg sodium hydroxide solution of 40 ° Be and 20 kg soda, coupled. The dye is salted out for complete precipitation, filtered, pressed and dried. He colors Wool and silk, waterfast, blue-violet.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE289030C true DE289030C (en) |
Family
ID=544095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT289030D Active DE289030C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE289030C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6607651B2 (en) | 1998-09-10 | 2003-08-19 | Cws Parts Company | Process and system for treating the discharge stream from an ion exchanger |
-
0
- DE DENDAT289030D patent/DE289030C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6607651B2 (en) | 1998-09-10 | 2003-08-19 | Cws Parts Company | Process and system for treating the discharge stream from an ion exchanger |
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