DE117894C - - Google Patents
Info
- Publication number
- DE117894C DE117894C DENDAT117894D DE117894DA DE117894C DE 117894 C DE117894 C DE 117894C DE NDAT117894 D DENDAT117894 D DE NDAT117894D DE 117894D A DE117894D A DE 117894DA DE 117894 C DE117894 C DE 117894C
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- brownish
- phenol
- bromodeoxyalizarin
- green
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000975 dye Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical class C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000007965 phenolic acids Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 3
- 240000007817 Olea europaea Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229940079877 Pyrogallol Drugs 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- CNEHAAOFZBHVPH-UHFFFAOYSA-L N.C([O-])([O-])=O.[Na+].[Na+] Chemical compound N.C([O-])([O-])=O.[Na+].[Na+] CNEHAAOFZBHVPH-UHFFFAOYSA-L 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- ZXYNGLRGFYLTQZ-UHFFFAOYSA-M [Zn]Cl Chemical compound [Zn]Cl ZXYNGLRGFYLTQZ-UHFFFAOYSA-M 0.000 description 1
- 235000020127 ayran Nutrition 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die in der Patentschrift 117923 beschriebenen Halogenderivate des Desoxyalizarins und seiner Analogen condensiren sich in überraschend leichter Weise mit Phenolen zu Farbstoffen, welche sich vom Phenylanthracen ableiten.Those described in patent 117923 Halogen derivatives of deoxyalizarin and its analogs condense surprisingly easily with phenols to form dyes, which are derived from phenylanthracene.
Vermischt man z. B. das in obiger Patentschrift beschriebene Bromdesoxyalizarinbromid mit Phenol, so findet unter reichlicher Entwickelung von Bromwasserstoff die Condensation bereits bei gewöhnlicher Temperatur statt.If you mix z. B. the bromodeoxyalizarin bromide described in the above patent with phenol, condensation takes place with copious evolution of hydrogen bromide already takes place at ordinary temperature.
Dadurch unterscheidet sich das Verfahren ganz wesentlich von demjenigen der Patentschrift 108836, nach welcher aus Anthrachinon und seinen Derivaten mit Resorcin (die Verwendung anderer Phenole ist weder beschrieben noch beansprucht) unter Anwendung hoher Temperaturen und grofser' Mengen energisch wirkender Condensationsmittel Gemenge chemisch nicht definirter Producte entstehen. This makes the process very different from that of the patent specification 108836, according to which from anthraquinone and its derivatives with resorcinol (the use other phenols is neither described nor claimed) using high temperatures and large amounts energetic condensation agents, mixtures of chemically undefined products arise.
Die nach vorliegendem Verfahren erhaltenen Condensationsproducte sind hingegen einheitliche wohl charakterisirte und leicht krystallisirbare Substanzen.By contrast, the condensation products obtained by the present process are uniform well-characterized and easily crystallizable substances.
Von dem Verfahren der Patentschrift 109344 unterscheidet sich das vorliegende dadurch, dafs das erstere nicht die Darstellung von Substitutionsproducten, sondern diejenige von Additionspr-oducten von keinem ausgeprägten . Farbstoffcharakter zum Gegenstand hat.The present method differs from the method of patent specification 109344 in that that the former is not the representation of substitution products, but that of Addition products of none pronounced. Has the character of a dye as its subject.
Wie schon erwähnt, besteht vorliegendes Verfahren darin, dafs man das betreffende Halogenderivat mit dem Phenol zusammenbringt, sei es direct, bei gewöhnlicher oder wenig erhöhter Temperatur, sei es unter Zusatz eines indifferenten Lösungsmittels, so dafs die Körper in Lösung oder flüssigem Zustande auf einander wirken können. In allen Fällen kann die Reaktion ohne Zusatz eines Condensationsmittels bewerkstelligt werden; manchmal ist es jedoch aus praktischen Gründen zweckmäfsig, ein solches, wie z. B. Chlorzink, in kleinen Mengen zuzufügen.As already mentioned, the present procedure consists in that one Brings halogen derivative with the phenol, be it directly, with ordinary or slightly elevated temperature, be it with the addition of an inert solvent, so that the bodies in solution or in a liquid state can act on one another. In all cases the reaction can be accomplished without the addition of a condensation agent; sometimes However, for practical reasons it is expedient to use one such. B. Chlorzinc, in add small amounts.
Es ist im Allgemeinen nicht nothwendig, die Halogenderivate in trockenem Zustande zu verwenden, man kann sie vielmehr zweckmäfsig im eisessigfeuchten Zustande benutzen, wie sie z. B. nach den Beispielen der Patentschrift 117923 erhalten werden.In general it is not necessary to treat the halogen derivatives in a dry state use, they can rather be used expediently in a condition that is moist with glacial acetic acid, how they z. B. be obtained according to the examples of patent 117923.
Die so erhaltenen Condensationsproducte sind im Allgemeinen in Wasser schwer löslich, mehr oder weniger leicht löslich. in Alkohol, Eisessig u. s. w., woraus sie leicht krystallisirt erhalten werden können.The condensation products obtained in this way are generally sparingly soluble in water, more or less easily soluble. in alcohol, glacial acetic acid, etc., from which it easily crystallizes can be obtained.
Sie sind in Alkalien leicht löslich und besitzen einen ausgesprochenen Beizenfarbstoffcharakter. Chrombeizen werden z. B. in gelben bis olivegrünen Nuancen angefärbt.They are easily soluble in alkalis and have a pronounced mordant character. Chrome stains are z. B. colored in yellow to olive green shades.
Das Verfahren wird durch folgende Beispiele erläutert:The procedure is illustrated by the following examples:
Das nach dem Beispiel II der Patentschrift 117923 aus 10 kg Desoxyalizarin erhaltene, noch eisessigfeuchte Bromirungsproduct wird mit 10 kg Phenol zusammengerührt. Die Masse wird flüssig und es entweichen Ströme von Bromwasserstoffsäure. Man rührt nun so lange, indem man zum Schlufs etwas erwärmt, bis die Bromwasserstoffentwickelung aufhört und die Masse anfängt, krümelig zu werden.The obtained from 10 kg deoxyalizarin according to Example II of patent specification 117923, The bromination product still moist with glacial acetic acid is stirred together with 10 kg of phenol. the The mass becomes liquid and streams of hydrobromic acid escape. One stirs now so long, by heating a little at the end, until the evolution of hydrogen bromide ceases and the mass starts to get crumbly.
Man behandelt dann mit heifsem Wasser, um das überschüssige Phenol zu entfernen, und krystallisirt den Rückstand aus verdünntem Alkohol unter Zusatz von wenig Thierkohle um.It is then treated with hot water to remove the excess phenol, and crystallizes the residue from dilute alcohol with the addition of a little animal charcoal around.
Man erhält so den Farbstoff in Form von hellgelben Krystallen, welche sich in Natron-The dye is obtained in the form of pale yellow crystals, which are in soda
lauge mit intensiv orangegelber, in concentrirter Schwefelsäure mit gelber Farbe lösen. Thonerdebeizen werden in rein gelben, Chrombeizen in gelbholzähnlichen, licht- und walkechten Nuancen angefärbt.Dissolve lye with an intense orange-yellow color, in concentrated sulfuric acid with a yellow color. Clay pickling are stained in pure yellow, chrome stains in yellowwood-like, light and whackfast nuances.
Die Elementaranalyse ergab:The elemental analysis showed:
60,38 und 60,19 pCt. Kohlenstoff,
3,38 und 3,41 pCt. Wasserstoff
übereinstimmend mit der Formel:60.38 and 60.19 pCt. Carbon,
3.38 and 3.41 pCt. hydrogen
in accordance with the formula:
OHOH
OHOH
welche 60,20 pCt. Kohlenstoff und 3,27 pCt. Wasserstoff verlangt.which 60.20 pCt. Carbon and 3.27 pCt. Requires hydrogen.
In ähnlicher Weise werden die übrigen Condensationsproducte dargestellt.The other condensation products are represented in a similar way.
Die Condensationsproducte von Bromdesoxyalizarinbromid mit p-Kresol, Resorcin, Salicylsäure, ß-Naphtol sind in ihren äufseren und färbenden Eigenschaften ähnlich dem eben beschriebenen Product. Das Condensationsproduct mit Pyrogallol ζ. B. krystallisirt in prachtvollen, metallisch grün glänzenden Krystallen und färbt Chrombeizen intensiv olive an.The condensation products of bromodeoxyalizarin bromide with p-cresol, resorcinol, Salicylic acid and ß-naphtol are similar in their external and coloring properties described product. The condensation product with pyrogallol ζ. B. crystallizes in splendid, metallic green shining crystals and intensely colors chrome stains olive on.
Die charakteristischen Eigenschaften einiger Vertreter dieser Farbstoff klasse sind in folgender Tabelle zusammengestellt:The characteristic properties of some representatives of this class of dye are as follows Table compiled:
in cone.
Schwefelsäuresolution
in cone.
sulfuric acid
in Natrium
carbonatsolution
in sodium
carbonate
chromgebeizte
WolleColoring on
chrome-stained
Wool
. +
PhenolChlorodeoxy alizarin
. +
phenol
dann bräun
lich gelbfirst yellow,
then tan
yellow
grünlich gelbyellowj then
greenish yellow
bräunlich
gelbyellow, slowly
brownish
yellow
+
PhenolBromodeoxyalizarin
+
phenol
bräunlich
gelbyellow to
brownish
yellow
gelbbrownish
yellow
+
ResorcinBromodeoxyalizarin
+
Resorcinol
gelbbrownish.
yellow
gelbbrownish
yellow
gelbbrownish
yellow
gelbbrownish
yellow
+
PyrogallolBromodeoxyalizarin
+
Pyrogallol
gelbbrownish
yellow
bräunlich
gelbyellow to
brownish
yellow
+
SalicylsäureBromodeoxyalizarin
+
Salicylic acid
bräunlich
gelbgreen to
brownish
yellow
gelbbrownish
yellow
+
ß-NaphtolBromodeoxyalizarin
+
ß-naphtol
+
PhenolBromodeoxyanthrapurpurine
+
phenol
hraungelb.yellow- .
brownish yellow.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE117894C true DE117894C (en) |
Family
ID=387129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT117894D Active DE117894C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE117894C (en) |
-
0
- DE DENDAT117894D patent/DE117894C/de active Active
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