DE45788C - Process for the preparation of naphthylenediamines - Google Patents
Process for the preparation of naphthylenediaminesInfo
- Publication number
- DE45788C DE45788C DENDAT45788D DE45788DA DE45788C DE 45788 C DE45788 C DE 45788C DE NDAT45788 D DENDAT45788 D DE NDAT45788D DE 45788D A DE45788D A DE 45788DA DE 45788 C DE45788 C DE 45788C
- Authority
- DE
- Germany
- Prior art keywords
- naphthylenediamines
- acid
- naphthylenediamine
- dioxynaphthalene
- naphthalene disulfonic
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000000875 corresponding Effects 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 monooxy Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Wie bereits in der Patentschrift No. 45549, betreffend die Darstellung eines αα-Naphtylendiamins, ausgeführt worden ist, lassen sich sämmtliche Dioxynaphtaline durch Erhitzen mit Ammoniak bezw. Ammoniak entbindenden Mitteln leichter als die Monooxyderivate des Naphtalins in die entsprechenden Amidoderivate überführen. Alle so entstehenden Naphtylendiamine sind von sehr wesentlichem technischen Interesse, da aus denselben Azofarbstoffe erzeugt werden können, welche ungeheizte Baumwolle direct anfärben. Die neuen Farbstoffe unterscheiden sich von den bekannten Benzidinderivaten durch ihre Unempfindlichkeit gegen Säuren.As already mentioned in patent no. 45549, relating to the preparation of an αα-naphthylenediamine, has been carried out, all of the dioxynaphthalines can be added by heating Ammonia resp. Ammonia relievers easier than the monooxy derivatives of the Convert naphthalene into the corresponding amido derivatives. All naphthylenediamines formed in this way are of very significant technical interest, as they are used to produce azo dyes which dye unheated cotton directly. The new dyes differ from the known benzidine derivatives by their insensitivity against acids.
Es wurden Naphtylendiamine dargestellt:Naphthylenediamines were represented:
1. aus dem Dioxynaphtalin, entstanden aus der α - Naphtalindisulfosäure von E b e r t & Merz bezw. aus der entsprechenden Naphtolsulfosäure; 1. from dioxynaphthalene, created from α-naphthalene disulphonic acid from E b e r t & Merz respectively from the corresponding naphthol sulfonic acid;
2. aus dem Dioxynaphtalin, entstanden aus der β-Naphtalindisulfosäure von Eben & Merz bezw. aus der Schaffer'sehen ß-Naphtolsulfosäure; 2. from dioxynaphthalene, created from β-naphthalene disulfonic acid from Eben & Merz respectively from Schaffer's view ß-naphthol sulfonic acid;
3. aus dem Dioxynaphtalin, entstanden aus der et-ß-Naphtalindisulfosäure bezw. der "entsprechenden Naphtolsulfosäure (Patent No. 45229).3. from the dioxynaphthalene, arose from the et-ß-naphthalene disulfonic acid respectively. the "corresponding Naphthol sulfonic acid (Patent No. 45229).
Zur Gewinnung dieser Naphtylendiamine wird in der Weise verfahren, dafs die entsprechenden Dioxynaphtaline mit Ammoniak oder Ammoniaksalzen in Druckgefäfsen auf Temperaturen von 150 bis 3oo° erhitzt werden.To obtain these naphthylenediamines, the procedure is that the corresponding Dioxynaphthalines with ammonia or ammonia salts in pressure vessels at temperatures be heated from 150 to 3oo °.
Nach einigen Stunden findet sich beim Oeffhen das entstandene Naphtylendiamin auskrystallisirt vor. Die salzsauren Salze der drei neuen Naphtylendiamine sind in Wasser leicht löslich and lassen sich durch Behandeln mit salpetriger Säure leicht in Tetrazoverbindungen überführen.After a few hours, on opening, the naphthylenediamine formed is found to have crystallized out before. The hydrochloric acid salts of the three new naphthylenediamines are easily soluble in water and can be treated with easily convert nitrous acid into tetrazo compounds.
Das der α-Naphtalindisulfosäure entsprechende Naphtylendiamin schmilzt bei i6i°.The one corresponding to α-naphthalene disulphonic acid Naphthylenediamine melts at 16 °.
Das der ß-Naphtalindisulfosäure entsprechende β j - β 3 - Naphtylendiamin schmilzt bei 216 bis 218°.The β j - β 3 - naphthylenediamine corresponding to ß-naphthalene disulfonic acid melts at 216 up to 218 °.
Das der α - β - Naphtalindisulfosäure entsprechendeNaphtylendiamin erstarrt bei gewöhnlicher Temperatur nicht.The naphthylenediamine corresponding to α - β - naphthalene disulfonic acid does not solidify at ordinary temperature.
Besonders leicht sind die isomeren 3 Naphtylendiamine durch die aus den Tetrazoverbindungen derselben entstehenden Azofarbstoffe zu unterscheiden. Durchweg erhält man durch Combination der Tetrazoverbindung desjenigen Naphtylendiamins, welches bezüglich der Stellung der Amidogruppen der ß-Naphtalindisulfosäure von Eben & Merz bezw. der ß-Naphtolsulfosäure von Schäffer entspricht, mit Phenolen und Aminen die blauesten bezw. die rothesten Nuancen.The isomeric 3 naphthylenediamines are particularly light because of those from the tetrazo compounds to differentiate the azo dyes formed from the same. Consistently one obtains through combination the tetrazo compound of that naphthylenediamine, which with respect to the position of the amido groups of ß-naphthalene disulfonic acid from Eben & Merz respectively. of ß-naphthol sulfonic acid von Schäffer corresponds, with phenols and amines the bluest respectively. the reddest nuances.
Es ist diesem Naphtylendiamin die Constitution Cl0He(NH 2 J3 1 zuzuschreiben. The constitution C 10 H e ( NH 2 J 3 1 is ascribed to this naphthylenediamine.
Bezüglich der Nuancen der erzielten Azofarbstoffe folgt diesem in der Farbenscala dasWith regard to the nuances of the azo dyes achieved, this follows this in the color scale
bekannte aj-α3-Naphtylendiamin (De Aguiar, Ber. 3, 27, Zinin, Ann. 85, 328, Patent No. 45549). Die aus diesem entstehenden Azofarbstoffe sind bereits wesentlich violetter bezw. gelber als die aus dem Vorgenannten erhaltenen.known aj-α 3 -naphthylenediamine (De Aguiar, Ber. 3, 27, Zinin, Ann. 85, 328, Patent No. 45549). The resulting from this azo dyes are already much more violet bezw. yellower than those obtained from the aforementioned.
Noch violettere bezw. gelbere Nuancen erzielt man durch Combination der Tetrazoverbindung desjenigen Naphtylendiamins, welches der α-Naphtalindisulfosäure von Ebert &Merz bezw. der ß-Naphtolsulfosäure des Patentes No. 42112 entspricht.Even more violet or Yellow nuances are achieved by combining the tetrazo compound of that naphthylenediamine which corresponds to the α-naphthalene disulfonic acid from Ebert & Merz respectively the β-naphthol sulfonic acid of patent no. 42112 corresponds.
Nach dem bisher vorliegenden wissenschaftlichen Material ist dasselbe als ßj-ß4-Naphtylendiamin zu bezeichnen.According to the scientific material available to date, it is to be referred to as βj-β 4 -naphthylenediamine.
Diejenigen Azofarbstoffe, welche aus dem ct-ß-Naphtylendiamin, entsprechend dem a-ß-Dioxynaphtalin des Patenies No. 45229, entstehen, unterscheiden sich sehr wesentlich durch den ihnen fast durchweg eigenthUmlichen braunen Ton.Those azo dyes which are derived from ct-ß-naphthylenediamine, corresponding to the a-ß- dioxynaphthalene of patent no. 45229, differ very essentially in their brown tone, which is almost entirely their own.
Was die anderen bereits früher bekannten Naphtylendiamine betrifft, so lassen sich aus denselben entweder überhaupt keine Tetrazoverbindungen erhalten, oder die entsprechenden Azofarbstoffe besitzen nicht das Vermögen, direct die Baumwolle anzufärben.As for the other previously known naphthylenediamines, we can omit the same either received no tetrazo compounds at all, or the corresponding ones Azo dyes do not have the power to dye cotton directly.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE45788C true DE45788C (en) |
Family
ID=320935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT45788D Expired - Lifetime DE45788C (en) | Process for the preparation of naphthylenediamines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE45788C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0372282A2 (en) * | 1988-12-02 | 1990-06-13 | Bayer Ag | Process for the preparation of 1,5-dihydroxy and 1,5 diaminonaphthalene |
-
0
- DE DENDAT45788D patent/DE45788C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0372282A2 (en) * | 1988-12-02 | 1990-06-13 | Bayer Ag | Process for the preparation of 1,5-dihydroxy and 1,5 diaminonaphthalene |
| EP0372282A3 (en) * | 1988-12-02 | 1990-08-08 | Bayer Ag | Process for the preparation of 1,5-dihydroxy and 1,5 diaminonaphthalene |
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