DE121836C - - Google Patents
Info
- Publication number
- DE121836C DE121836C DENDAT121836D DE121836DA DE121836C DE 121836 C DE121836 C DE 121836C DE NDAT121836 D DENDAT121836 D DE NDAT121836D DE 121836D A DE121836D A DE 121836DA DE 121836 C DE121836 C DE 121836C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dye
- dyes
- added
- oxidation
- 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.)
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Links
- 239000000975 dye Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 8
- 210000002268 Wool Anatomy 0.000 claims description 5
- 230000001264 neutralization Effects 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- USPVTJCHQHJFBQ-UHFFFAOYSA-N 3-chloro-N,N-diethylaniline Chemical compound CCN(CC)C1=CC=CC(Cl)=C1 USPVTJCHQHJFBQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- CHHCCYVOJBBCIY-UHFFFAOYSA-N 3-chloro-N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC(Cl)=C1 CHHCCYVOJBBCIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000001045 blue dye Substances 0.000 claims description 2
- 230000000875 corresponding Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift 88085 sm<i blaue Farbstoffe beschrieben, die durch Condensation der aus der Monosulfosäure des Tetramethyldiamidodiphenylmethans durch Oxydation entstehenden Hydrosulfosäure mit Sulfosäuren alkylirter aromatischer Amine und Oxydation der gebildeten Leukoverbindungen dargestellt werden. Die so gewonnenen Farbstoffe sind typische Säurefarbstoffe, d. h. sie färben Wolle nur in saurem Bade kräftig, während Wolle in neutralem Bade nur schwach gefärbt wird. Es wurde nun die wichtige Beobachtung gemacht, dafs man kräftig neutral färbende, werthvolle blaue Wollfarbstoffe erhält, wenn man die erwähnte Hydrolsulfosäure mit m - Chlordiäthylanilin oder m - Chlordimethylanilin condensirt und die entstehenden Leukokörper oxydirt.In the patent specification 88085 sm < i blue dyes are described which are prepared by condensation of the hydrosulfonic acid formed by oxidation from the monosulfonic acid of tetramethyldiamidodiphenylmethane with sulfonic acid alkylated aromatic amines and oxidation of the leuco compounds formed. The dyes obtained in this way are typical acid dyes, ie they only dye wool vigorously in an acid bath, while wool is only weakly dyed in a neutral bath. The important observation has now been made that valuable blue wool dyes with a strong neutral color are obtained if the hydrolsulfonic acid mentioned is condensed with m-chlorodiethylaniline or m-chlorodimethylaniline and the leuco bodies formed are oxidized.
11,7 kg 90 procentiges Natriumsalz der Tetramethyldiamidodiphenylmethanmonosulfosäure werden in einem mit Rührwerk versehenen Bottich in 800 1 Wasser gelöst und mit 11,7 kg Salzsäure 200B.. angesäuert. Hierauf werden dieser Lösung unter starkem Rühren 33,6 kg einer 21,15 proc. Bleisuperoxydpaste zugesetzt. Nach Y2 Stunde ist die Oxydation beendet, worauf man 5,5 kg m-Chlordiäthylanilin und 3,5 kg Salzsäure noch zufügt und rasch auf 80° C. erwärmt. Nach einem etwa 3 stündigen Rühren bei dieser Temperatur ist die blaue Farbe der Lösung verschwunden und die Condensation beendet. Man giebt alsdann noch so viel Salzsäure zu, dafs die Leukoverbindung ganz in Lösung geht, und fällt das Blei mit Glaubersalz aus. Aus dem Filtrat scheidet sich beim genauen Neutralisiren mit Soda die Leukoverbindung als grauweifser, in der Kälte pulveriger Niederschlag aus. Dieser wird filtrirt und getrocknet.11.7 kg sodium salt of 90 procentiges Tetramethyldiamidodiphenylmethanmonosulfosäure be dissolved in a vat equipped with a stirrer in 800 1 water and acidified .. 11.7 kg of hydrochloric acid 20 0 B. Then 33.6 kg of a 21.15 percent are added to this solution with vigorous stirring. Lead peroxide paste added. After 2 hours, the oxidation is complete, whereupon 5.5 kg of m-chlorodiethylaniline and 3.5 kg of hydrochloric acid are added and the mixture is quickly heated to 80.degree. After stirring for about 3 hours at this temperature, the blue color of the solution has disappeared and the condensation has ended. Then enough hydrochloric acid is added that the leuco compound goes completely into solution, and the lead is precipitated with Glauber's salt. On precise neutralization with soda, the leuco compound separates out of the filtrate as a gray-white precipitate, powdery in the cold. This is filtered and dried.
Zur Ueberführung in den Farbstoff werden 10,3 kg getrocknete Leukobase in 7 kg Salzsäure und 500 1 Wasser gelöst und unter starkem Rühren mit 22,4 kg einer 21,15 proc. Bleisuperoxydpaste versetzt. Nach beendeter Oxydation, während welcher sich der Farbstoff zum Theil ausscheidet, wird auf 80° C. erwärmt, mit Glaubersalz das Blei gefällt, dann mit Ammoniak übersättigt und filtrirt. Aus dem Filtrat wird der Farbstoff ausgesalzen.To convert into the dye, 10.3 kg of dried leuco base are added to 7 kg of hydrochloric acid and 500 1 of water dissolved and with vigorous stirring with 22.4 kg of a 21.15 proc. Lead peroxide paste added. After the oxidation has ended, during which the dye is partially precipitated, is heated to 80 ° C., the lead is precipitated with Glauber's salt, then oversaturated with ammonia and filtered. The dye is salted out from the filtrate.
Der getrocknete Farbstoff bildet ein kupferroth glänzendes Pulver, ziemlich schwer löslich in kaltem, leicht aber in heifsem Wasser mit rein blauer Farbe. Alkohol löst ihn schon in der Kälte leicht. Verdünnte wässerige Lösungen werden von Alkalien nicht verändert, Mineralsäuren fällen bei vorsichtigem Zusatz den Farbstoff als blaue Flocken aus, löslich im Säureüberschufs mit grüner Farbe.The dried dye forms a shiny copper-red powder, rather difficult to dissolve in cold, light but in hot water with a pure blue color. Alcohol dissolves him easy even in the cold. Diluted aqueous solutions are not changed by alkalis, If carefully added, mineral acids precipitate the dye as blue flakes, soluble in excess acid with a green color.
Der Farbstoff färbt Wolle in neutralem wie in saurem Bade rein blau und alkaliecht, andererseits ist er wegen seines basischen Charakters auch befähigt, tannirte Baumwolle kräftig zu färben.The dye dyes wool in neutral and acidic baths pure blue and alkaline, on the other hand, because of its basic character, it is also capable of tannin cotton to be colored vigorously.
Ersetzt man in diesem Beispiel das m-Chlordiäthylanilin durch die äquivalente Menge m-Chlordimethylanilin, so erhält man einenReplacing the m-chlorodiethylaniline in this example by the equivalent amount of m-chlorodimethylaniline, one obtains one
Farbstoff mit ganz ähnlichen Eigenschaften, jedoch etwas rötherer Nuance.Dye with very similar properties, but with a slightly redder shade.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE121836C true DE121836C (en) |
Family
ID=390809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT121836D Active DE121836C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE121836C (en) |
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0
- DE DENDAT121836D patent/DE121836C/de active Active
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