DEC0009651MA - - Google Patents
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- Publication number
- DEC0009651MA DEC0009651MA DEC0009651MA DE C0009651M A DEC0009651M A DE C0009651MA DE C0009651M A DEC0009651M A DE C0009651MA
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dye
- dichlorobenzene
- hours
- carboxylic acid
- 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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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- BJCTXUUKONLPPK-UHFFFAOYSA-N 9-oxofluorene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C2=C1 BJCTXUUKONLPPK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000984 vat dye Substances 0.000 claims description 4
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- BXJVHCYXCBNDRF-UHFFFAOYSA-N 7-oxobenzo[a]phenalene-2-carbonyl chloride Chemical compound C1=C(C=C2C=CC=C3C(=O)C4=CC=CC=C4C1=C23)C(=O)Cl BXJVHCYXCBNDRF-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- KOJOUCAVSDKDPR-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=1C=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=1NC(=O)C1=CC=CC=C1 KOJOUCAVSDKDPR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 14. Juli 1954 Bekanntgemacht am 28. Juni 1956Registration date: July 14, 1954. Advertised on June 28, 1956
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
PATENTANMELDUNGPATENT APPLICATION
KLASSE 22b GRUPPE 3os C 9651 IVb/22b CLASS 22b GROUP 3os C 9651 IVb / 22b
Dr. Werner Zerweck, Frankfurt/M.,
und Dr. Ernst Heinrich, Frankfurt/M.-FechenheimDr. Werner Zerweck, Frankfurt / M.,
and Dr. Ernst Heinrich, Frankfurt / M.-Fechenheim
sind als Erfinder genannt wordenhave been named as inventors
Cassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt/M.-FechenheimCassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt / M.-Fechenheim
Verfahren zur Herstellung eines KüpenfarbstoffsProcess for the preparation of a vat dye
Es wurde gefunden, daß man einen neuen Küpenfarbstoff erhält,' wenn man Fluorenon-2-carbonsäure oder deren funktionelle Derivate mit ι -Amino - 5 - benzoylamino - anthrachinon kondenIt has been found that there is a new vat dye obtained 'if you use fluorenone-2-carboxylic acid or its functional derivatives ι -Amino - 5 - benzoylamino - anthraquinone condensates
siert.sated.
Der erhaltene Farbstoff entspricht der FormelThe dye obtained corresponds to the formula
0 NH-CO—,0 NH-CO—,
>— CO — NH 0 609 547/493> - CO - NH 0 609 547/493
C 9651 IVb/'22b C 9651 IVb / '22b
Er färbt und druckt pflanzliche Faser in lebhaften goldgelben Tönen von hervorragenden Echtheitseigenschaften. It dyes and prints vegetable fibers in vivid golden yellow tones with excellent fastness properties.
Aus der schweizerischen Patentschrift 151 331 ist es bekannt, daß man durch Umsetzung von Benzanthron-2-carbonsäurechlorid mit 1-Amino-· 5-benzoylaminoanthrachinon einen Küpenfarbstoff erhält, der die pflanzliche Faser in goldgelben Tönen färbt. Demgegenüber weist der erfmdungsgemäß erhaltene Farbstoff beträchtliche Vorzüge in Licht- und Wetterechtheit sowie hinsichtlich der Faserschädigung auf.From Swiss patent specification 151 331 it is known that by reacting benzanthrone-2-carboxylic acid chloride with 1-amino · 5-benzoylaminoanthraquinone is given a vat dye that turns the vegetable fiber into a golden yellow Tones colors. In contrast, the dye obtained according to the invention has considerable advantages Light and weather fastness as well as with regard to fiber damage.
Ein Gemisch aus 350 Teilen o-Dichlorbenzol, 24 Teilen Thionylchlorid und 16,8 Teilen Fluorenon-2-carbonsäure (hergestellt gemäß den Angaben der »Organic Syntheses« Bd. 28, S. 63) wird 4 Stunden auf i6o° erhitzt. Hierauf wird das überschüssige Thionylchlorid im Vakuum abdestilliert und die Reaktionsbrühe mit 17 Teilen i-Amino-5-benzoylamino-anthrachinon versetzt. Anschließend wird 12 Stünden auf i6o° erhitzt. Nach dem Erkalten wird der so gebildete Farbstoff abgesaugt und auf dem Sauger zunächst mit o-Dichlorbenzol und dann mit Methanol ausgewaschen und getrocknet. Das rotstichiggelbe Farbstoffpulver löst sich in Schwefelsäure mit braunoranger Farbe und färbt und druckt die pflanzliche Faser aus rotvioletterA mixture of 350 parts of o-dichlorobenzene, 24 parts of thionyl chloride and 16.8 parts of fluorenone-2-carboxylic acid (prepared according to the information in "Organic Syntheses" Vol. 28, p. 63) is 4 hours heated to 160 °. The excess thionyl chloride is then distilled off in vacuo and the Reaction broth with 17 parts of i-amino-5-benzoylamino-anthraquinone offset. Then it is heated to 160 ° for 12 hours. After cooling down the dye thus formed is suctioned off and on the suction device first with o-dichlorobenzene and then washed out with methanol and dried. The reddish yellow dye powder dissolves in Sulfuric acid with brown-orange color and dyes and prints the vegetable fiber from red-violet
Claims (1)
Schweizerische Patentschrift Nr. 151,331.Considered publications:
Swiss patent specification No. 151,331.
Family
ID=
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