DE83011C - - Google Patents
Info
- Publication number
- DE83011C DE83011C DENDAT83011D DE83011DA DE83011C DE 83011 C DE83011 C DE 83011C DE NDAT83011 D DENDAT83011 D DE NDAT83011D DE 83011D A DE83011D A DE 83011DA DE 83011 C DE83011 C DE 83011C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amidonaphthol
- mol
- disulfonic acid
- tolidine
- 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
- 239000002253 acid Substances 0.000 claims description 21
- 239000000975 dye Substances 0.000 claims description 10
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 9
- NUIURNJTPRWVAP-UHFFFAOYSA-N Tolidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 claims description 9
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000003086 colorant Substances 0.000 description 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Blue Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 75432 ist eine αΛ α3-Amidonaphtol - ß2 ß4 - disulfosäure beschrieben, die aus der Naphtalin-ß2ß4-disulfosäure durch Sulfirung, Nitrirung, Reduction und Alkalischmelze entsteht. Diese Säure liefert, mit Tetrazokörpern combinirt, werthvolle blaue Farbstoffe. Sie läfst sich zur Darstellung symmetrischer und gemischter Disazofarbstoffe verwenden. In ihrem allgemeinen Charakter stehen diese den Farbstoffen nahe, die aus O1 a4 - Amidonaphtol-ß2 ß3- disulfosäure (H) erhalten werden, sie sind leicht löslich, fixiren sich aber trotzdem sehr gut auf ungeheizter Baumwolle. Bemerkenswerth ist ihre Säurebeständigkeit. In the patent specification No. 75432 an α Λ α 3 -amidonaphthol - ß 2 ß 4 - disulfonic acid is described, which is formed from naphthalene-ß 2 ß 4 -disulfonic acid by sulfation, nitration, reduction and alkali fusion. This acid, combined with tetrazo bodies, gives valuable blue coloring matter. It can be used to represent symmetrical and mixed disazo dyes. In their general character these are close to the dyes which are obtained from O 1 a 4 - amidonaphthol-β 2 β 3 - disulfonic acid (H); they are easily soluble, but nevertheless fix themselves very well on unheated cotton. Their acid resistance is remarkable.
Von den Farbstoffen aus der H-Säure sowohl, wie überhaupt von den entsprechenden Disazoderivaten der bekannten Amidonaphtolsulfosäuren unterscheiden sich die neuen Farbstoffe sehr wesentlich in ihrem Verhalten beim Diazotiren und Entwickeln auf der Faser. Die Entwickelungen zeigen durchweg tief blaue Töne; während z. B. die Farbstoffe aus Tetrazokörpern und Amidonaphtoldisulfosäure H bei der Entwickelung mit ß-Naphtol graue Töne liefern (s. Patentschrift Nr. 75992), erhält man bei Einwirkung dieses Körpers auf die mit salpetriger Säure behandelten Färbungen der analogen neuen Farbstoffe indigoblaue Färbungen von vorzüglicher ,Lichtechtheit und absoluter Waschechtheit.Of the dyes from the H-acid as well as of the corresponding ones in general Disazo derivatives of the known amidonaphthol sulfonic acids differ from the new dyes very essential in their behavior when diazotizing and developing on the fiber. the Developments consistently show deep blue tones; while z. B. the dyes from tetrazo bodies and amidonaphtoldisulfonic acid H at give gray tones when developed with ß-naphtol (see patent specification no. 75992), is obtained when this body acts on the dyeings of the nitrous acid treated analogous new dyes indigo blue dyeings of excellent, lightfastness and absolute washfastness.
Das Verfahren der Herstellung der Farbstoffe ergiebt sich aus folgenden Beispielen.The method for preparing the dyes is shown in the following examples.
18,4 kg Benzidin werden in die Tetrazoverbindung übergeführt und diese in die mit Soda alkalisch gehaltene Lösung von 65 kg O1 a3 - Amidonaphtol - ß2 ß4 - disulfosäure eingetragen. Nach einigen Stunden ist der gebildete Farbstoff als dunkelblau gefärbter Niederschlag ausgeschieden; oder18.4 kg of benzidine are converted into the tetrazo compound and this is added to the solution of 65 kg of O 1 a 3 - amidonaphthol - ß 2 ß 4 - disulfonic acid, which is kept alkaline with soda. After a few hours, the dye formed has separated out as a dark blue precipitate; or
21,2 kg Tolidin werden in die Tetrazoverbindung übergeführt und diese rasch mit der alkalischen Lösung von 32 kg al a3-Amidonaphtol -ß2 ß4-disulfosäure vermischt. Die Bildung des Zwischenkörpers findet augenblicklich statt. Man trägt dann eine Lösung von 23 kg α, α2 - Naphtolsulfosäure ein. Der Farbstoff wird mit Kochsalz ausgefällt und abfiltrirt.21.2 kg of tolidine are converted into the tetrazo compound and this is quickly mixed with the alkaline solution of 32 kg of a 1 a 3 amidonaphthol -β 2 β 4 -disulfonic acid. The formation of the intermediate body takes place instantaneously. A solution of 23 kg of α, α 2 -naphthol sulfonic acid is then introduced. The dye is precipitated with common salt and filtered off.
In analoger Weise werden andere Combinationen erhalten. Die Nuancen der technisch wichtigsten sind folgende:Other combinations are obtained in an analogous manner. The nuances of the technical the most important are:
vonι mol. Tetrazo compound
from
mittied together
with
ungeheizte
Baumwollecolors
unheated
cotton
Tolidin
Benzidin
Tolidin Benzidine
Tolidine
Benzidine
Tolidine
desgleichen
ι Mol. U1 ß3-Amidonaphtol-ß2 ß4-disulfosäure
und ι Mol. Amidonaphtoldisulfosäure H
desgleichen2 mol. K 1 o 3 -amidonaphthol- (3 2 ß 4 -disulfonic acid
likewise
ι Mol. U 1 ß 3 -amidonaphthol-ß 2 ß 4 -disulfonic acid
and ι Mol. Amidonaphtholdisulfonic acid H
likewise
grünblau
blau
grünblaudark blue
green Blue
blue
green Blue
vonι mol. Tetrazo compound
from
mittied together
with
ungeheizte
Baumwollecolors
unheated
cotton
Tolidin
Benzidin
Tolidin
Benzidin
Tolidin
Benzidin
Tolidin
Benzidin
Tolidin Benzidine
Tolidine
Benzidine
Tolidine
Benzidine
Tolidine
Benzidine
Tolidine
Benzidine
Tolidine
und ι Mol. jz-Amidonaphtolsulfosäure
desgleichen
ι Mol. Ci1 a3-Amidonaphtol-ß2 ß4-disulfosäure
und ι Mol. «!-Naphtol-^-sulfosäure
desgleichen
ι Mol. Ci1 Ct3-Amidonaphtol-ß2 ß^-disulfosäure
und ι Mol. Salicylsäure
desgleichen
ι Mol. H1 a3-Amidonaphtol-ß2 ß4-disulfosäure
und ι Mol. ct-Naphtylamin
desgleichen
ι Mol. U1 ct3-Amidonaphtol-ß2 ß4-disulfosäure
und ι Mol. m-Phenylendiamin
desgleichenι MoL O 1 a 3 -amidonaphthol-ß 2 ß 4 -disulfonic acid
and ι mol. jz-amidonaphthol sulfonic acid
likewise
ι Mol. Ci 1 a 3 -amidonaphthol-ß 2 ß 4 -disulfonic acid
and ι mol. «! -Naphthol - ^ - sulfonic acid
likewise
ι Mol. Ci 1 Ct 3 -amidonaphtol-ß 2 ß ^ -disulfonic acid
and ι mol. salicylic acid
likewise
ι Mol. H 1 a 3 -amidonaphtol-ß 2 ß 4 -disulfonic acid
and ι mol. ct-naphthylamine
likewise
ι Mol. U 1 ct 3 -amidonaphthol-ß 2 ß 4 -disulfonic acid
and ι mol. m-phenylenediamine
likewise
schwarzblau
violettblau
blau
braun
braun
violett
violett
braunviolett
braunviolett.blue black
black blue
violet blue
blue
Brown
Brown
violet
violet
brown purple
brown purple.
Claims (1)
Die Ausführungsformen des im Anspruch 1Process for the preparation of disazo dyes from the Ct 1 a 3 -amidonaphthol-ß 2 ß 4 -disulfonic acid of patent no. 75432, in that the tetrazo derivatives of p-diamines with 2 molecules of this acid or with 1 molecule of the same and 1 molecule of one Amine or phenol.
The embodiments of the claim 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE83011C true DE83011C (en) |
Family
ID=355373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT83011D Active DE83011C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE83011C (en) |
-
0
- DE DENDAT83011D patent/DE83011C/de active Active
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