DE81036C - - Google Patents
Info
- Publication number
- DE81036C DE81036C DENDAT81036D DE81036DA DE81036C DE 81036 C DE81036 C DE 81036C DE NDAT81036 D DENDAT81036 D DE NDAT81036D DE 81036D A DE81036D A DE 81036DA DE 81036 C DE81036 C DE 81036C
- Authority
- DE
- Germany
- Prior art keywords
- mol
- acid
- dye
- salicylic acid
- intermediate product
- 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- YYNCOERMULFLJD-UHFFFAOYSA-N 4-(4-aminophenyl)-3-nitroaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1[N+]([O-])=O YYNCOERMULFLJD-UHFFFAOYSA-N 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N Potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- IPVTTYAHKXZGCQ-QOCHGBHMSA-N (4Z)-3-oxo-4-[(4-sulfonaphthalen-1-yl)hydrazinylidene]naphthalene-2,7-disulfonic acid Chemical compound C1=CC=C2C(N/N=C3/C4=CC=C(C=C4C=C(C3=O)S(=O)(=O)O)S(O)(=O)=O)=CC=C(S(O)(=O)=O)C2=C1 IPVTTYAHKXZGCQ-QOCHGBHMSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/14—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
In der Patentschrift Nr. 44797, Zusatz zum Patent Nr. 31658, ist gezeigt, dafs man durch Einwirkung von 1 Mol. Tetrazodiphenyl bezw. Tetrazoditolyl auf eine alkalische Lösung von ι Mol. Salicylsäure zu einem Zwischenproduct gelangt, welches noch eine verfügbare Diazogruppe enthält und daher befähigt ist, sich mit Phenolen und Aminen zu Azofarbstoffen zu combiniren. Ein unter Benutzung dieses Verfahrens erhältlicher Farbstoff ist sodann in der Patentschrift Nr. 72867 beschrieben. Zur Darstellung desselben wird das im oben genannten Patente benutzte Tetrazodiphenyl durch dessen Nitrosubstitutionsproduct, die Tetrazoverbindung des Mononitrobenzidins (N H2 : N O2 = 1 : ■$) ersetzt und die letztere mit 1 Mol. Salicylsäure und sodann mit 1 Mol. aj-Naphtol-a2-monosulfosäure combinirt. Es entsteht so ein gemischter Disazofarbstoff, welcher auf Wolle ein ebenso schönes wie echtes Ponceäuroth erzeugt.In patent specification No. 44797, addendum to patent No. 31658, it is shown that by the action of 1 mol. Tetrazoditolyl on an alkaline solution of ι mol. Salicylic acid arrives at an intermediate product which still contains an available diazo group and is therefore able to combine with phenols and amines to form azo dyes. A dye obtainable using this process is then described in U.S. Patent No. 72867. To represent the same, the tetrazodiphenyl used in the above-mentioned patent is replaced by its nitro substitution product, the tetrazo compound of mononitrobenzidine (NH 2 : N O 2 = 1: ■ $) and the latter with 1 mol. Salicylic acid and then with 1 mol. Aj-naphthol -a 2 -monosulfonic acid combined. The result is a mixed disazo dye, which creates a beautiful and real Ponceäuroth on wool.
Zu einem noch blaustichigeren rothen Farbstoff gelangt man, wenn man in dem Verfahren des Patentes Nr. 72867 an Stelle der Tetrazoverbindung des Mononitrobenzidins die Tetrazoverbindung des m-Nitrotolidins (N H2 : N O2 = I,: ■$) verwendet und dementsprechend die letztere zunächst mit 1 Mol. Salicylsäure kuppelt und das erhaltene Zwischenproduct sodann auf ι Mol. aj-Naphtol-a2-monosulfosäure (Nevile-Winther) einwirken läfst.An even more bluish red dye is obtained if, in the process of Patent No. 72867, instead of the tetrazo compound of mononitrobenzidine, the tetrazo compound of m-nitrotolidine (NH 2 : NO 2 = I,: ■ $) is used and, accordingly, the latter initially with 1 mole of salicylic acid and the intermediate product obtained is then allowed to act on ι mole of α-naphthol-α 2 -monosulfonic acid (Nevile-Winther).
Der so erhaltene Farbstoff erzeugt auf gebeizter und ungeheizter Wolle sehr klare blaustichig rothe Nuancen, die sich durch hervorragende Echtheit gegen Säure und Wäsche, Licht und Walke auszeichnen.The dye thus obtained produces very clear bluish tints on stained and unheated wool red nuances that stand out due to their excellent fastness to acids and laundry, Light and Walke distinguish.
25,7 kg m-Nitrotolidin (NH2: N O2 = 1 : ■$) (erhältlich durch Behandeln einer Lösung von ι Mol. Tolidinsulfat in cone. Schwefelsäure mit ι Mol. Kalisalpeter öder der entsprechenden Menge Salpeterschwefelsäure) werden in üblicher Weise in die Tetrazoverbindung verwandelt und die letztere sodann in eine eiskalte, mit 60 kg Soda versetzte Lösung von 14 kg Salicylsäure einfliefsen gelassen. Nach Beendigung der Bildung des Zwischenproductes setzt man eine ebenfalls gut gekühlte Lösung von 26 kg des Natronsalzes. der aj-Naphtol-c^-monosulfosäure(Nevile-Winther)zu. Nach i2stündigem Stehen erwärmt man zur Vollendung der Farbstofifbildung auf 300, läfst noch einige Stunden stehen und isolirt den fertigen Farbstoff nach dem Aufkochen durch Zusatz von Kochsalz.25.7 kg of m-nitrotolidine (NH 2 : N O 2 = 1: ■ $) (obtainable by treating a solution of 1 mole of tolidine sulfate in cone. Sulfuric acid with 1 mole of potassium nitrate or the corresponding amount of nitric sulfuric acid) are used in the customary manner converted into the tetrazo compound and the latter is then allowed to flow into an ice-cold solution of 14 kg of salicylic acid to which 60 kg of soda has been added. After the formation of the intermediate product has ended, a likewise well-cooled solution of 26 kg of the sodium salt is added. the aj-naphtol-c ^ -monosulfonic acid (Nevile-Winther). After standing i2stündigem is heated to complete the Farbstofifbildung 0 to 30, läfst stand for some hours and the final dye insulated after boiling by the addition of sodium chloride.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE81036C true DE81036C (en) |
Family
ID=353545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT81036D Active DE81036C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE81036C (en) |
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0
- DE DENDAT81036D patent/DE81036C/de active Active
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