DE122065C - - Google Patents
Info
- Publication number
- DE122065C DE122065C DENDAT122065D DE122065DA DE122065C DE 122065 C DE122065 C DE 122065C DE NDAT122065 D DENDAT122065 D DE NDAT122065D DE 122065D A DE122065D A DE 122065DA DE 122065 C DE122065 C DE 122065C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- naphtylamine
- naphthylamine
- acid
- blue
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 8
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- HPNTZCAYLSSXRP-UHFFFAOYSA-N 4-phenylnaphthalen-1-amine Chemical compound C12=CC=CC=C2C(N)=CC=C1C1=CC=CC=C1 HPNTZCAYLSSXRP-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 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
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/053—Amino naphthalenes
- C09B31/057—Amino naphthalenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Vr 122065 KLASSE 22 a. Vr 122065 CLASS 22 a.
Nach der Patentschrift 118655 werden bisher unbekannte sekundäre Disazofarbstoffe erhalten, wenn man o.x ai - Phenylnaphtylaminsulfosäure mit den Diazoverbindungen der dort aufgezählten Amidoazoproducte. combinirt.According to patent specification 118655, hitherto unknown secondary disazo dyes are obtained if o. X a i - phenylnaphthylamine sulfonic acid with the diazo compounds of the amidoazo products listed there. combined.
Es hat sich nun weiter ergeben, dafs man an Stelle der Phenylnaphtylaminsulfosäure auch das analoge p-Tolylproduct mit Vortheil verwenden kann. Dasselbe wird bekanntlich durch Erhitzen der Ci1 ci4-Naphtylaminsulfosäure mit p-Toluidin in Gegenwart eines halogenwasserstoffsauren Salzes dieser Base erhalten (vergl. die Patentschrift 71158).It has now also been found that the analogous p-tolyl product can also be used with advantage in place of the phenylnaphthylamine sulfonic acid. The same is known to be obtained by heating the Ci 1 ci 4 -naphtylaminesulfonic acid with p-toluidine in the presence of a hydrohalic acid salt of this base (cf. Patent 71158).
Man gelangt so zu Producten von hohem technischen Werth.In this way one arrives at products of high technical value.
Das Verfahren zur Herstellung dieser Farbstoffe ist dem in der Patentschrift 118655 beschriebenen ganz analog, da der Ersatz der dort verwendeten Phenylnaphtylaminsulfosäure durch die Tolylnaphtylaminsulfosäure keinerlei Aenderung bedingt. The process for making these dyes is that described in patent specification 118655 quite analogous, since the replacement of the phenylnaphtylamine sulfonic acid used there by the tolylnaphtylamine sulfonic acid no change required.
Zur Gewinnung der Amidoazozwischenproducte werden die in der Patentschrift 118655. genannten Amine bezw. substituirten Amine nach dem Diazotiren mit einer der sogen. Cl eve'sehen a-Naphtylamin-ß-monosulfosäuren (aj ß3- oder U1 ß4-) am besten in schwach essigsaurer Lösung gekuppelt.To obtain the amidoazo intermediate products, the amines mentioned in patent 118655. respectively. substituted amines after diazotizing with one of the so-called. Cl eve's see a-naphthylamine-ß-monosulfonic acids (aj ß 3 - or U 1 ß 4 -) best coupled in a weakly acetic acid solution.
Die so erhaltenen Amidoazoverbindungen werden dann nach dem Weiterdiazotiren mit der obengenannten Tolylnaphtylaminsulfosäure vortheilhaft in schwach essigsaurer Lösung combinirt und die fertig gebildeten Farbstoffe nach dem Alkalischmachen durch Aussalzen, Abfiltriren u. s. w. in üblicher Weise isolirt.The amidoazo compounds thus obtained are then, after further diazotizing, with the above-mentioned tolylnaphthylamine sulfonic acid advantageously combined in a weakly acetic acid solution and the finished dyes after making them alkaline by salting out, filtering off and so on isolated in the usual way.
In der folgenden Tabelle sind die Nuancen einer Anzahl der neuen Farbstoffe angeführt.The following table shows the nuances of a number of the new dyes.
Farbstoff, erhalten durch Kuppeln von Ci1 ai -Tolylnaphtylaminsulfosäure
mit der diazotirten Amidoazoverbindung aus:Dye obtained by coupling Ci 1 a i -Tolylnaphtylaminsulfosäure
with the diazotized amidoazo compound from:
Anilin -\- Ci1 ß3-Naphtylaminsulfosäure blau,Aniline - \ - Ci 1 ß 3 -Naphthylamine sulfonic acid blue,
Anilin -|- Ci1 ß4-Naphtylaminsulfosäure . . . . blau,Aniline - | - Ci 1 ß 4 -naphtylamine sulfonic acid. . . . blue,
m-Sulfanilsäure -(- a.x ß3-Naphtylaminsulfosäure blau,m-sulfanilic acid - (- a. x ß 3 -naphtylamine sulfonic acid blue,
m-Sulfanilsäure -|- U1 ß4-Naphtylaminsulfosäure blau,m-sulfanilic acid - | - U 1 ß 4 -naphtylamine sulfonic acid blue,
p-Amidosalicylsäure -\- Ci1 ß3-Naphtylaminsulfosäure blau,p-Amidosalicylic acid - \ - Ci 1 ß 3 -Naphthylamine sulfonic acid blue,
p-Amidosalicylsäure + U1 ß4-Naphtylaminsulfosäure blau,p-amidosalicylic acid + U 1 ß 4 -naphtylamine sulfonic acid blue,
ti-Naphtylamin + U1 ß3-Naphtylaminsulfosäure blau,ti-naphtylamine + U 1 ß 3 -naphtylamine sulfonic acid blue,
a-Naphtylamin -(- o.x ß4-Naphtylaminsulfosäure blau,a-naphtylamine - (- o. x ß 4 -naphtylamine sulfonic acid blue,
ß-Naphtylamin + Ci1 ß3-Naphtylaminsulfosäure blau,ß-naphtylamine + Ci 1 ß 3 -naphtylamine sulfonic acid blue,
ß-Naplitylamin -|- Ci1 ß4-Naphtylaminsulfosäure blau,ß-Naplitylamine - | - Ci 1 ß 4 -Naphthylamine sulfonic acid blue,
CL1 a2-Naphtylaminsulfosäure -f- αλ ßg-Naphtylaminsulfosäure grünstichig blau, CL 1 a 2 -naphtylamine sulfonic acid -f- α λ ß g -naphtylamine sulfonic acid greenish blue,
A1 a2-Naphtylaminsulfosä'ure -|- U1 ß4-Naphtylaminsulfosäure grünstichig blau,A 1 a 2 -Naphthylamine sulfonic acid - | - U 1 ß 4 -Naphthylamine sulfonic acid greenish blue,
ßj ßg-Naphtylaminsulfosäure -f- A1 ß3-Naphtylaminsulfosäure grünstichig blau,ßj ßg-naphtylamine sulfonic acid -f- A 1 ß 3 -naphtylamine sulfonic acid greenish blue,
ßj ß3-Naphtylaminsulfosäure -\- Ci1 ß4-Naphtylaminsulfosäure grünstichig blau,ßj ß 3 -Naphtylamine sulfonic acid - \ - Ci 1 ß 4 -Naphtylaminsulfosäure greenish blue,
p-Nitranilin -|- K1 ßg-Naphtylaminsulfosäure. , blaugrün,p-Nitraniline - | - K 1 ßg-naphthylamine sulfonic acid. , blue green,
p-Nitranilin -|- U1 ß4-Naphtylaminsulfosäure ■ · blaugrün.p-Nitraniline - | - U 1 ß 4 -Naphthylamine sulfonic acid ■ · blue-green.
Claims (1)
Neuerung in dem Verfahren des Patentes 118655 zur Darstellung sekundärer Disazofarbstoffe, darin bestehend, dafs man die dort an letzter Stelle benutzte Ci1 a4-Phenylnaphtylaminmonosulfosäure durch die p-ToIyI-A1 a4- naphtylaminmonosulfosäure ersetzt. Patent Claims:
Innovation in the process of patent 118655 for the preparation of secondary disazo dyes, consisting in the fact that the Ci 1 a 4 -phenylnaphthylamine monosulfonic acid used last there is replaced by the p-Tolyl-A 1 a 4 -naphthylamine monosulfonic acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE122065C true DE122065C (en) |
Family
ID=391016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT122065D Active DE122065C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE122065C (en) |
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0
- DE DENDAT122065D patent/DE122065C/de active Active
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