AT56109B - Process for the preparation of disazo dyes. - Google Patents
Process for the preparation of disazo dyes.Info
- Publication number
- AT56109B AT56109B AT56109DA AT56109B AT 56109 B AT56109 B AT 56109B AT 56109D A AT56109D A AT 56109DA AT 56109 B AT56109 B AT 56109B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- disazo dyes
- dyes
- acid
- aminonaphthol
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- -1 ß-naphthylamine sulfonic acids Chemical class 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- JAOZKJMVYIWLKU-UHFFFAOYSA-N sodium 7-hydroxy-8-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalene-1,3-disulfonic acid Chemical compound C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)O)N=NC3=C(C=CC4=CC(=CC(=C43)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] JAOZKJMVYIWLKU-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Disazofarbstoffen.
In der deutschen Patentschrift Nr. 129388 werden lichtechte, rote bis rotviolette Baumwollfarbstoffe beschrieben, die erhalten werden durch Vereinigung von tetrazotierter p. p'-Diaminodiphenylharnstoff-m-m'-disulfosäure (dargestellt nach D. R. P. Nr. 140613) in neutraler oder saurer Lösung mit 2. 8-Aminonaphtol und dessen Sulfosäuren bzw. den in der Aminogruppe al kylierten Derivaten dieser Körper.
Es wurde nun gefunden, dass man Farbstoffe mit den gleichen wertvollen Eigenschaften, aber von erheblich grösserer Klarheit, erhält, wenn man die Tetrazoverbindung der p-p'-Diaminodiphenylharnstoff-w m'-disulfonsäure nur mit einem Molekü l obiger Komponenten in saurer oder neutraler Lösung vereinigt und an zweiter Stelle eine Monosulfosäure des ss-Naphtyamins oder seiner Alkylderivate verwendet. Eine weitere Steigerung der Klarheit der Nuancen wird erreicht, wenn man auch das andere Molekül der sauer gekuppelten 2. 8-Aminonaphtol-6-sulfosäure durch eine der oben erwähnten Sulfosäuren des ss-Naphtylamins und seiner Atkylderivate ersetzt.
Dass bei diesem Ersatz die Lichtechtheit erhalten bleiben würde, war nicht vorauszusehen, da bekanntlich die durch saure Kupplung der 2. 8-Aminoaphtolsulfosäure erhäl@ lichen Baumwollfarbstoffe im allgemeinen sich durch Lichtechtheit auszeichnen, den Farbstoffen aus ss-Naphtylaminsulfosäuren im allgemeinen diese Eigenschaft aber nicht zukommt.
B e i s p i e t l.
Die nach dz It. P. Nr. 129388 isolierte Tetrazoverbindung aus 402 Teilen der
EMI1.1
hildeto Farbstoff gibt auf Baumwolle ein sehr lichtechtes, aussergewöhnlich klares, blaustichiges Rot. Beispiel) 2.
EMI1.2
können auch andere Alkylderivate dieser Säuren, wie Athyl- und Benzylderivate, verwendet werden oder es können auch die ss-Naphtylaminsulfosäuren selbst benutzt werden. Die 2.8-Aminonaphtol-6-sulfosäure kann in gleicher Weise durch ihre Alkyt-oder A'yt- derivate vertreten werden. Die Nuancen der gebildeten Farbstoffe liegen zwischen orange und violettrot.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of disazo dyes.
German Patent No. 129388 describes lightfast, red to red-violet cotton dyes which are obtained by combining tetrazotized p. p'-Diaminodiphenylurea-m-m'-disulfonic acid (prepared according to D. R. P. No. 140613) in neutral or acidic solution with 2.8-aminonaphthol and its sulfonic acids or the derivatives of these compounds alkylated in the amino group.
It has now been found that dyes with the same valuable properties, but of considerably greater clarity, are obtained if the tetrazo compound of p-p'-diaminodiphenylurea-w m'-disulfonic acid is obtained with only one molecule of the above components in acidic or neutral form Solution combined and used in the second place a monosulfonic acid of ss-naphtyamine or its alkyl derivatives. A further increase in the clarity of the nuances is achieved if the other molecule of the acid-coupled 2, 8-aminonaphthol-6-sulfonic acid is also replaced by one of the above-mentioned sulfonic acids of β-naphthylamine and its alkyl derivatives.
It was not foreseeable that the lightfastness would be retained with this replacement, since it is known that the cotton dyes obtainable by acidic coupling of the 2, 8-aminoaphthol sulfonic acid are generally characterized by lightfastness, but the dyes made from ß-naphthylamine sulfonic acids generally do not have this property .
I e p i e t
The tetrazo compound isolated according to dz It. P. No. 129388 from 402 parts of
EMI1.1
hildeno dye gives cotton a very lightfast, exceptionally clear, bluish red. Example) 2.
EMI1.2
Other alkyl derivatives of these acids, such as ethyl and benzyl derivatives, can also be used, or the β-naphthylamine sulfonic acids themselves can also be used. The 2,8-aminonaphthol-6-sulfonic acid can be represented in the same way by its alkyl or a'yte derivatives. The nuances of the dyes formed are between orange and purple-red.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE56109X | 1910-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT56109B true AT56109B (en) | 1912-11-11 |
Family
ID=5628648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT56109D AT56109B (en) | 1910-08-08 | 1911-07-27 | Process for the preparation of disazo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT56109B (en) |
-
1911
- 1911-07-27 AT AT56109D patent/AT56109B/en active
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