DE142565C - - Google Patents
Info
- Publication number
- DE142565C DE142565C DENDAT142565D DE142565DA DE142565C DE 142565 C DE142565 C DE 142565C DE NDAT142565 D DENDAT142565 D DE NDAT142565D DE 142565D A DE142565D A DE 142565DA DE 142565 C DE142565 C DE 142565C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- dye
- reports
- nitrobenzene
- color
- 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
- 239000000975 dye Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 3
- 229940100198 ALKYLATING AGENTS Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- MBFLUZMECMTQLU-ONEGZZNKSA-N 2-[(E)-2-(5-carbamimidoyl-1-benzofuran-2-yl)ethenyl]-1-benzofuran-5-carboximidamide Chemical compound NC(=N)C1=CC=C2OC(/C=C/C=3OC4=CC=C(C=C4C=3)C(=N)N)=CC2=C1 MBFLUZMECMTQLU-ONEGZZNKSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic sulfonic acids Chemical class 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910000906 Bronze Inorganic materials 0.000 description 1
- 102100013068 CDCA4 Human genes 0.000 description 1
- 101700022879 CDCA4 Proteins 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N Methyl bisulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HYEKBBUUXFWKKZ-UHFFFAOYSA-K sodium;zinc;trichloride Chemical compound [Na+].[Cl-].[Cl-].[Cl-].[Zn+2] HYEKBBUUXFWKKZ-UHFFFAOYSA-K 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc 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
- C09B17/00—Azine dyes
- C09B17/06—Fluorindine or its derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Das Fluorindin und Isofluorindin bezw. ihre arylierten Derivate sind trotz ihres Farbstoffcharakters technisch nicht verwertbar wegen ihrer Schwerlöslichkeit und Alkaliempfindlichkeit; die Salze sind blau oder grünblau, die freien Basen rot bezw. grün gefärbt.The fluorindine and isofluorindine respectively. their arylated derivatives are despite their dye character technically not usable because of their poor solubility and alkali sensitivity; the salts are blue or green-blue, the free bases red respectively. colored green.
Alkaliechte, leicht lösliche Derivate dieser Körper entstehen jedoch dann, wenn diese Körper mit alkylierenden Mitteln behandelt . werden. Als solche Mittel sind Schwefelsäuredialkylester, Ester aromatischer Sulfosäuren besonders brauchbar, aber auch Halogenalkyle führen zum Ziele. Die Nuance der erhaltenen Alkylderivate, welche als Fluorindiniumverbindüngen bezeichnet werden können, ist violettblau bis blau. Sie bilden leicht lösliche Salze und geben auf tierischer und pflanzlicher Faser licht- und waschechte Färbungen von großer Intensität.Alkali-like, easily soluble derivatives of these bodies are created when these Body treated with alkylating agents. will. Such agents are sulfuric acid dialkyl esters, Esters of aromatic sulfonic acids are particularly useful, but haloalkyls also achieve the goal. The nuance of the received Alkyl derivatives, which can be referred to as fluoroindinium compounds, are violet-blue to blue. They form easily soluble salts and give light and washfast colorations of great color to animal and vegetable fibers Intensity.
Das Verfahren ergibt sich aus folgenden Beispielen:The procedure results from the following examples:
I. 22 kg Diphenylflnorindin (Fischer und Hepp, Berichte XXIII, 2790; Kehrmann und Bürgin, Berichte XXIX, 1251) werden in 150 kg Nitrobenzol heiß gelöst und zu der tiefroten Lösung bei 1500C. 16 kg Dimethylsulfat hinzugegeben. Die Farbe der Lösung geht in Blau über und es beginnt die Ausscheidung des methylschwefelsauren Salzes des alkylierten Farbstoffs. Sobald die Reaktion beendet ist, destilliert man das Nitrobenzol mit Wasserdampf ab, versetzt die dunkelblaue zurückbleibende Lösung mit etwas Soda, um etwa unangegriffenes Ausgangsmaterial auszufällen, filtriert und fällt den Farbstoff mit Kochsalz oder Chlorzink aus. Der Farbstoff löst sich leicht in Wasser mit blauer Farbe, die durch Ammoniak nicht geändert wird. Vom Alkohol sowie von konzentrierter Schwefelsäure wird er mit blauer Farbe gelöst. Er färbt tannierte Baumwolle lebhaft blau. Die Färbungen sind wasch- und lichtecht.I. 22 kg of diphenylflnorindine (Fischer and Hepp, reports XXIII, 2790; Kehrmann and Bürgin, reports XXIX, 1251) are dissolved in 150 kg of hot nitrobenzene and 16 kg of dimethyl sulfate are added to the deep red solution at 150 ° C. The color of the solution turns blue and the methylsulfuric acid salt of the alkylated dye begins to precipitate. As soon as the reaction has ended, the nitrobenzene is distilled off with steam, the dark blue remaining solution is mixed with a little soda to precipitate any unaffected starting material, filtered and the dye is precipitated with sodium chloride or zinc chloride. The dye dissolves easily in water with a blue color that ammonia does not change. Alcohol and concentrated sulfuric acid dissolve it with a blue color. It dyes tanned cotton vividly blue. The colors are washable and lightfast.
II. 45 kg Isodiphenylfluorindin (Kehrmann und Bürgin, Berichte XXIX, 1820; Kehrmann und Dur et, Berichte XXXI, 2442) werden in Form seines Chlorhydrats mit 10 kg Soda und 25 kg Dimethylsulfat bei 50 bis 6o° C. ~ zusammengerieben. Man trägt dann die Masse in kochendes Wasser ein, filtriert und fällt den Farbstoff mit Kochsalz oder Chlorzink aus. Er färbt ein lebhaftes, sehr wasch- und lichtechtes Blau und zeigt die gleiche Reaktion wie der im Beispiel I beschriebene Farbstoff.II. 45 kg isodiphenylfluorindine (Kehrmann and Bürgin, reports XXIX, 1820; Kehrmann and Dur et, reports XXXI, 2442) are in the form of its chlorohydrate with 10 kg Soda and 25 kg dimethyl sulfate rubbed together at 50 to 60 ° C. ~. You then carry the mass in boiling water, filtered and precipitated the dye with common salt or zinc chloride. It colors a vivid, very washable and lightfast blue and shows the same reaction as the dye described in Example I.
III. 10 kg Di-p-tolylfluorindin werden inIII. 10 kg of di-p-tolylfluorindine are used in
80 kg Nitrobenzol kochend gelöst und bei 1600C. 10 kg p-Toluolsulfosäureester hinzugegeben. Nach etwa zwölfstündiger Einwirkung bei 1500 C. ist die Reaktion beendet. Man verfährt dann weiter wie im Beispiel I angegeben. Der Farbstoff zeigt die gleichen Eigenschaften wie die Diphenylverbindung.80 kg of nitrobenzene dissolved at the boil and added at 160 ° C. 10 kg of p-toluenesulfonic acid ester. After about twelve hours of action at 150 ° C., the reaction has ended. Then proceed as indicated in Example I. The dye shows the same properties as the diphenyl compound.
Das hier verwendete Di-p-tolylfluorindin wird aus o-Amidophenyl-p-tolylamin nach demselben Verfahren gewonnen, welches zur Darstellung des Diphenylfluorindins aus o-Amidodiphenylamin dient und Berichte XXIX, S. 1252 beschrieben ist. Es kristallisiert aus Nitrobenzol in bronzeglänzenden Blättchen. Es schmilzt nicht bis 3000 C.The di-p-tolylfluorindine used here is obtained from o-amidophenyl-p-tolylamine by the same process which is used to prepare the diphenylfluorindine from o-amidodiphenylamine and is described in Reports XXIX, p. 1252. It crystallizes from nitrobenzene in shiny bronze flakes. It does not melt until 300 0 C.
Claims (1)
Publications (1)
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DE142565C true DE142565C (en) |
Family
ID=410114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT142565D Active DE142565C (en) |
Country Status (1)
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4448617A (en) * | 1980-08-05 | 1984-05-15 | Aichi Steel Works, Ltd. | Steel for a vehicle suspension spring having good sag-resistance |
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0
- DE DENDAT142565D patent/DE142565C/de active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4448617A (en) * | 1980-08-05 | 1984-05-15 | Aichi Steel Works, Ltd. | Steel for a vehicle suspension spring having good sag-resistance |
US4574016A (en) * | 1980-08-05 | 1986-03-04 | Aichi Steel Works, Ltd. | Method of treating steel for a vehicle suspension spring having a good sag-resistance |
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