DE197034C - - Google Patents
Info
- Publication number
- DE197034C DE197034C DE1907197034D DE197034DA DE197034C DE 197034 C DE197034 C DE 197034C DE 1907197034 D DE1907197034 D DE 1907197034D DE 197034D A DE197034D A DE 197034DA DE 197034 C DE197034 C DE 197034C
- Authority
- DE
- Germany
- Prior art keywords
- naphthylamine
- black
- sulfonic acid
- aminonaphtol
- acid
- 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
- 239000000975 dye Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 210000002268 Wool Anatomy 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- -1 α-naphthylamine sulfonic acids Chemical class 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 230000001808 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 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
- 230000002378 acidificating Effects 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
fevkjtJi-Iurn' C6fevkjtJi-Iurn 'C6
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
— Ja 197034 KLASSE 22 a. GRUPPE - Yes 197034 CLASS 22 a. GROUP
Über sauer färbende Monoazofarbstoffe, die durch Kupplung von Diazoverbindungen mit dem ι -Amino-7-naphtol des Patentes 69458 erhältlich sind, ist bisher nichts bekannt geworden. Es wurde jetzt gefunden, daß durch Kupplung von Sulfosäuren des a-Naphtylamins und Derivaten desselben mit dem erwähnten Aminonaphtol in alkalischer Lösung Monoazofarbstoffe erhalten werden, die sich überraschenderweise als außerordentlich wertvolle Produkte erwiesen. Mit der Fähigkeit, auf Wolle aus saurem Bade sehr gut deckende braune bis tiefschwarze Nuancen zu liefern, verbinden sie die wertvolle Eigenschaft, vorzüglich zu egalisieren, gegen andauerndes Kochen in stark saurer Flotte, wie es in vielen Fällen für den Färber Erfordernis ist, beständig zu sein und weiße Baumwolleffekte nicht anzufärben. Da außerdem die Waschechtheit der Färbungen eine gute ist, die Ausgangsmaterialien für die Herstellung der Farbstoffe leicht zugänglich sind und die Herstellung selbst die denkbar einfachste ist, so kann das vorliegende Verfahren als ein technischer Fortschritt bezeichnet werden.Acid coloring monoazo dyes produced by coupling diazo compounds are obtainable with the ι-amino-7-naphtol of the patent 69458, nothing is known so far become. It has now been found that by coupling sulfonic acids of a-naphthylamine and derivatives thereof with the aforementioned aminonaphthol monoazo dyes are obtained in alkaline solution, which surprisingly turned out to be extremely valuable products. With the Ability to produce very good coverage of brown to deep black nuances on wool from an acid bath to deliver, they combine the valuable quality of excellently equalizing against the permanent Cooking in a strongly acidic liquor, as is required in many cases for the dyer is to be resistant and not to stain white cotton effects. In addition, since the washfastness of the dyeings is a good is that the starting materials for the preparation of the dyes are easily available are and the production itself is the simplest imaginable, the present method can can be described as a technical advance.
Die in üblicher Weise aus 31,7 kg ·ΐ·4~ naphtylaminsulfosaurem Natrium und 7 kg Natriumnitrit hergestellte Diazoverbindung wird unter kräftigem Rühren in die· mit überschüssiger Soda versetzte Lösung des Natriumsalzes von 16 kg 1 ■ 7-Arninonaphtol eingetragen. Die Kupplung ist nach kurzer Zeit beendet. Der abgeschiedene Farbstoff wird, erforderlichenfalls nach weiterem Aussalzen, abfiltriert und getrocknet. Er löst sich in Wasser mit blauvioletter Farbe und färbt Wolle aus saurem Bade je nach der ■ Menge des Farbstoffes in grauen bis violettschwarzen Tönen an. The usual way from 31.7 kg · ΐ · 4 ~ naphthylamine sulfonic acid sodium and 7 kg sodium nitrite produced diazo compound is mixed with vigorous stirring in the solution of the Sodium salt of 16 kg 1 ■ 7-aminonaphtol registered. The coupling ends after a short time. The deposited dye is, if necessary after further salting out, filtered off and dried. He solves itself in water with a blue-violet color and dyes wool from an acid bath depending on the ■ Amount of dye in gray to purple-black tones.
Ersetzt man das l-Amino-7-naphtol durch seine in der Aminogruppe alkylierten Derivate, wie Äthyl- oder Benzyl-1-amino-7-naphtol, die leicht durch Erhitzen einer wässerigen Suspension oder alkoholischen Lösung der freien Aminonaphtolbase mit Halogenalkylen bzw. Dialkylsulfat bei Gegenwart eines säurebindenden Mittels, wie Natriumacetat, Bicarbonat oder Soda usw., erhältlich sind und in allen organischen Lösungsmitteln leicht lösliche Produkte darstellen, so erhält man blauere Nuancen.If the l-amino-7-naphtol is replaced by its derivatives alkylated in the amino group, such as ethyl or benzyl-1-amino-7-naphthol, which is easily done by heating an aqueous suspension or alcoholic solution of the free aminonaphthol base with haloalkylene or dialkyl sulfate in the presence of an acid-binding one Agents such as sodium acetate, bicarbonate or soda etc. are available and readily available in all organic solvents represent soluble products, one obtains bluer nuances.
In der umstehenden Tabelle sind die Färbeeigenschaften einer Anzahl der neuen Farbstoffe angegeben.In the table below are the coloring properties a number of the new dyes.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT36215D AT36215B (en) | 1907-02-22 | 1908-04-08 | Process for the preparation of monoazo dyes. |
Publications (1)
Publication Number | Publication Date |
---|---|
DE197034C true DE197034C (en) |
Family
ID=459957
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1907197034D Expired - Lifetime DE197034C (en) | 1907-02-22 | 1907-02-22 |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE197034C (en) |
-
1907
- 1907-02-22 DE DE1907197034D patent/DE197034C/de not_active Expired - Lifetime
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