DE35615C - Process for the preparation of azo dyes ^ by combining tetrazoditolyl with et- and ^ 9-naphthylamine or their mono- and disulfonic acids - Google Patents
Process for the preparation of azo dyes ^ by combining tetrazoditolyl with et- and ^ 9-naphthylamine or their mono- and disulfonic acidsInfo
- Publication number
- DE35615C DE35615C DENDAT35615D DE35615DA DE35615C DE 35615 C DE35615 C DE 35615C DE NDAT35615 D DENDAT35615 D DE NDAT35615D DE 35615D A DE35615D A DE 35615DA DE 35615 C DE35615 C DE 35615C
- Authority
- DE
- Germany
- Prior art keywords
- naphthylamine
- tetrazoditolyl
- mono
- combining
- dyes
- 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
- 239000002253 acid Substances 0.000 title claims description 11
- 150000007513 acids Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims 2
- 239000000987 azo dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 20
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 7
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-Nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 claims description 2
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-Nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 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 2
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000000391 smoking Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- -1 β-naphthylamine 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
- 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
- C09B35/12—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from amines
Description
ο· ο Ii ο · ο II
KAISERLICHESIMPERIAL
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Zusatz - Patent zu No. 28753 vom 27. Februar 1884.Addition - Patent to No. 28753 of February 27, 1884.
Fatentirt im Deutschen Reiche vom 17. März 1885 ab. Längste Dauer: 26. Februar 1899.Fatentirt in the German Empire from March 17, 1885. Longest duration: February 26, 1899.
Die Tetrazoverbindungen des Tolidins, dargestellt durch alkalische Reduction von Ortho- oder Paranitrotoluol oder von einem Gemisch beider, dem technischen Nitrotoluol, können mit α- und ß-Naphtylamin und deren Mono- und Disulfosäuren schöne, theils sprit-, theils wasserlösliche Farbstoffe bilden, welche ungeheizte Baumwolle im Seifenbade intensiv gelbroth bis blauroth färben und von den entsprechenden Benzidinfarbstoffen durch ihre Nuance und gröfsere Echtheit gegen Licht und Säuren wesentlich verschieden sind. Während der von Böttiger in Lodz aus Tetrazodiphenyl mit a-Naphtionsäure erhaltene und im Handel unter dem Namen »Congo« bekannte rothe Farbstoff von den geringsten Spuren Essigsäure braun bis schwarz wird, zeigt der entsprechende Farbstoff aus Tetrazoditoiyi bei weitem nicht so grofse Empfindlichkeit gegen verdünnte Säuren und ist bedeutend lichtechter als dieser.The tetrazo compounds of tolidine, represented by the alkaline reduction of ortho- or paranitrotoluene or a mixture of both, technical grade nitrotoluene, can with α- and β-naphthylamine and their mono- and disulphonic acids are beautiful, partly gas-soluble, partly water-soluble Forms of dyes, which unheated cotton in a soap bath can be intensely yellow-red to Blue-red in color and from the corresponding benzidine dyes by their nuances and greater Fastness to light and acids are essentially different. During the von Böttiger obtained in Lodz from tetrazodiphenyl with a-naphthoic acid and sold under the Name »Congo« known red dye from the slightest traces of acetic acid to brown becomes black, the corresponding dye from Tetrazoditoiyi is nowhere near as large Sensitivity to dilute acids and is significantly more lightfast than this.
Ein noch gröfserer Unterschied zwischen den Benzidin- und Tolidinfarbstoffen ergiebt sich in Combination mit β - Naphtylaminsulfosäuren, seien dieselben durch directe Sulfirung von β - Naphtylamin oder durch Erhitzen von Sch äffe r'scher ß-Naphtolsulfosäure mit Ammoniak erhalten. In beiden Fällen bildet Tetrazodiphenyl mit denselben Farbstoffe, welche selbst in kochendem Wasser unlöslich und in der beschriebenen Form nicht auf Baumwolle zu fixiren, also technisch absolut werthlos sind. Tetrazoditoiyi dagegen bildet in Combination mit diesen Sulfosäuren Farbstoffe, welche in Wasser leicht löslich und durch ihre absolute Echtheit gegen starke Essigsäure und selbst gegen verdünnte mineralische Säuren und durch das Feuer ihrer Farbe sehr werthvoll sind.There is an even greater difference between the benzidine and tolidine dyes in Combination with β-naphthylamine sulfonic acids are said to be the same by direct sulfonation of β-naphthylamine or by heating Schäffe r'scher ß-naphthol sulfonic acid with ammonia obtain. In both cases, tetrazodiphenyl forms dyes with the same, which Insoluble even in boiling water and not in the form described on cotton to fix, that is, are technically absolutely worthless. Tetrazoditoiyi, on the other hand, forms in combination with these sulfonic acids dyes, which are easily soluble in water and by their absolute Fastness to strong acetic acid and even to dilute mineral acids and through the fire of their color are very valuable.
Man stellt diese Farbstoffe am besten in der Weise dar, dafs man wässerige Lösungen der Tetrazoditolylsalze in die wässerigen Lösungen der α- und ß-Naphtylaminsalze oder in die in Wasser fein suspendirten Mono- und Disulfosäuren des a- und β - Naphtylamins einlaufen läfst und die vorhandenen freien mineralischen Säuren durch Salze der organischen Säuren, z. B. durch essigsaures Natron, abstumpft. An Stelle der wässerigen Lösungen lassen sich auch die alkoholischen Lösungen, an Stelle der freien Säuren auch deren Salze in alkalischer Lösung verwenden.It provides these dyes in the best way is, that we aqueous solutions of Tetrazoditolylsalze in the aqueous solutions of α- and ß-Naphtylaminsalze or in that of the a- in water finely suspendirten mono- and disulfonic acids and β - enter Naphtylamins läfst and existing free mineral acids by salts of organic acids, z. B. by sodium acetate, dulls. Instead of the aqueous solutions, it is also possible to use alcoholic solutions, and instead of the free acids, their salts in alkaline solution can also be used.
Die so gebildeten spritlöslichen Farbstoffe werden durch Behandeln mit rauchender Schwefelsäure in wasserlösliche Farbstoffe übergeführt, die dann in ihren Eigenschaften grofse Äehnlichkeit mit den direct erhaltenen wasserlöslichen Farbstoffen zeigen, nur etwas stumpfer als diese sind.The thus formed fuel-soluble dyes are treated with smoking Sulfuric acid converted into water-soluble dyes, which then have great properties Show resemblance to the directly obtained water-soluble dyes, only somewhat more bluntly than these are.
Als Beispiel des genauen Verfahrens zur Darstellung dieser Farbstoffe mögen folgende dienen:As an example of the detailed method for preparing these dyes, the following may be given to serve:
I. a) ι 50 kg schwefelsaures Tolidin (Diamidoditolyl), erhalten aus technischem Nitrotoluol,I. a) ι 50 kg of sulfuric acid tolidine (diamidoditolyl), obtained from technical nitrotoluene,
werden in Wasser fein suspendirt, mit 50 kg Salzsäure von 210 B. versetzt und zu der mit Eis gekühlten Lösung 22,2 kg Natriumnitrit, in 10 1 Wasser gelöst, langsam hinzulaufen gelassen.be finely suspended, mixed in water with 50 kg of hydrochloric acid 21 0 B. and dissolved to the ice-cooled solution of 22.2 kg sodium nitrite in 10 1 of water, added slowly run.
Es bildet sich so das Tetrazoditolylchlorid.The tetrazoditolyl chloride is thus formed.
Diese Lösung setzen wir darauf zu einer wässerigen Lösung von 58 kg salzsaurem a- oder β - Naphtylamin, stumpfen die freie mineralische Säure durch Natriumacetat ab und lassen das Gemisch ca. 24 Stunden stehen. Der so erhaltene dunkelbraune bezw. hochrothe Niederschlag wird abfiltrirt und behufs Ueberführung in seine Sulfosäuren getrocknet.We then add this solution to an aqueous solution of 58 kg of hydrochloric acid or β - naphthylamine, the free mineral acid blunt by sodium acetate and let the mixture stand for about 24 hours. The dark brown respectively obtained in this way. bright red Precipitate is filtered off and dried to convert it into its sulfonic acids.
b) 50 kg des trockenen, spritlöslichen Farbstoffes werden unter Umrühren langsam in 150 kg rauchende Schwefelsäure von 20 pCt. Anhydridgehalt bei 150 C. eingetragen, die so erhaltene tiefblaue Schmelze so lange bei gewöhnlicher Temperatur stehen gelassen, bis die Sulfirung vollendet, darauf in Wasser gegossen und die ausgeschiedene Sulfosäure durch Behandeln mit Natronlauge oder Soda in ihr Natronsalz übergeführt.b) 50 kg of the dry, fuel-soluble dye are slowly stirred into 150 kg of fuming sulfuric acid of 20 pCt. Anhydride was added at 15 0 C., the deep blue melt thus obtained so long as at ordinary temperature allowed to stand until the completed Sulfirung, then poured into water and the precipitated sulfonic acid converted by treatment with sodium hydroxide or sodium carbonate in their sodium salt.
II. Das in derselben Weise wie bei La) erhaltene Tetrazoditolylchlorid wird zu 73 kg in Wasser fein suspendirte Naphtionsäure (schwerlösliche α - Naphtylaminsulfosäure) hinzugefügt, die freie mineralische Säure durch Hinzufügen von essigsaurem Natron abgestumpft und das Gemisch mehrere Tage unter häufigem Umrühren stehen gelassen.II. The tetrazoditolyl chloride obtained in the same manner as in La) is 73 kg in Finely suspended naphthoic acid (poorly soluble α-naphthylamine sulfonic acid) added to water, the free mineral acid blunted by adding acetic acid baking soda and that Let the mixture stand for several days with frequent stirring.
Es bildet sich so ein rothbrauner, schleimiger Niederschlag, der durch Erwärmen und Neutralisiren mit Natronlauge oder Soda in sein Natronsalz übergeführt wird.A red-brown, slimy precipitate is formed, which by heating and Neutralization with caustic soda or soda is converted into its sodium salt.
Beim Erkalten fällt der Farbstoff fast quantitativ als ein orangerothes Pulver aus, das, abfiltrirt, ungeheizte Baumwolle intensiv blauroth färbt.On cooling the dye precipitates almost quantitatively as an orange-red powder which, when filtered off, unheated cotton dyes intensely blue-red.
III. Einen scharlachrothen, säureechten Farbstoff, der in seiner Schönheit die oben beschriebenen Farbstoffe noch übertrifft, erhält man aus der β-Naphtylaminsulfosäure, gebildet durch Erhitzen der Schäffer'schen ß-Naphtolsulfosäure mit Ammoniak.III. A scarlet, acid-fast dye, the beauty of which is that described above Exceeding dyes is obtained from the β-naphthylamine sulfonic acid, formed by heating the Schäffer ß-naphthol sulfonic acid with ammonia.
^Nachdem man zu der wässerigen Lösung von 80 kg β - naphtylaminsulfosaures Natron überschüssige Sodalösung hinzugefügt hat, läfst man in dieselbe langsam unter Umrühren und Eiskühlung das wie bei La) erhaltene Tetrazoditolylchlorid einlaufen. Es bildet sich ein bräunlichrother Niederschlag, der sich nach ca. zwölfstündigem Stehen vollständig auflöst. Fügt man nun zu der so erhaltenen Farbstofflösung Kochsalzlösung hinzu, so fällt ein rother, schleimiger Niederschlag, der durch Erwärmen krystallinisch wird und das Natronsalz jenes oben beschriebenen Farbstoffes darstellt.^ After adding to the aqueous solution of 80 kg of β-naphthylaminesulfonate of soda has added excess soda solution, it is poured into the same slowly while stirring and Ice cooling the tetrazoditolyl chloride obtained as in La) come in. A brownish-red precipitate forms, which takes about twelve hours Standing completely dissolves. If you now add saline solution to the dye solution obtained in this way, a red, slimy precipitate, which becomes crystalline when heated, and the sodium salt that represents the dye described above.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE35615C true DE35615C (en) |
Family
ID=311465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT35615D Expired - Lifetime DE35615C (en) | Process for the preparation of azo dyes ^ by combining tetrazoditolyl with et- and ^ 9-naphthylamine or their mono- and disulfonic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE35615C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7477330B2 (en) | 2005-03-09 | 2009-01-13 | 3M Innovative Properties Company | Automatic darkening filter with offset polarizers |
| US7637622B2 (en) | 2005-10-11 | 2009-12-29 | 3M Innovative Properties Company | Control of an automatic darkening filter |
| US8042958B2 (en) | 2005-06-20 | 2011-10-25 | 3M Innovative Properties Company | Automatic darkening filter with automatic power management |
-
0
- DE DENDAT35615D patent/DE35615C/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7477330B2 (en) | 2005-03-09 | 2009-01-13 | 3M Innovative Properties Company | Automatic darkening filter with offset polarizers |
| US8042958B2 (en) | 2005-06-20 | 2011-10-25 | 3M Innovative Properties Company | Automatic darkening filter with automatic power management |
| US7637622B2 (en) | 2005-10-11 | 2009-12-29 | 3M Innovative Properties Company | Control of an automatic darkening filter |
| US7810937B2 (en) | 2005-10-11 | 2010-10-12 | 3M Innovative Properties Company | Control of an automatic darkening filter |
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