CH201529A - Process for the production of a vat dye of the anthraquinone acridone series. - Google Patents
Process for the production of a vat dye of the anthraquinone acridone series.Info
- Publication number
- CH201529A CH201529A CH201529DA CH201529A CH 201529 A CH201529 A CH 201529A CH 201529D A CH201529D A CH 201529DA CH 201529 A CH201529 A CH 201529A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- production
- dye
- vat dye
- blue
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title 1
- -1 anthraquinone acridone series Chemical class 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 3
- 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 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000126 substance 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/36—Amino acridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
Description
Verfahren zar Herstellung eines Nüpenfarbstoffes der Anthraeliinonaeridoureibe.
EMI0001.0004
Gegenstand <SEP> des <SEP> Hauptpatentes <SEP> ist <SEP> ein
<tb> Verfahren <SEP> zur <SEP> Herstellung <SEP> eines <SEP> Küperdarb stoffes <SEP> :der <SEP> Anthrar,hinenaeridonreihe, <SEP> naelt
<tb> welchem <SEP> man <SEP> 4-Amino-3-,sulfo-I-[6'-chlor l'-carboxy-29'-a.n,illdol-a.nthrar,hinon <SEP> in <SEP> belie bi,c.,er <SEP> Reihenf olge <SEP> der <SEP> Einwirkung <SEP> von <SEP> den
<tb> Aeri,do,n,rin"o"schluss <SEP> bewirkenden <SEP> Mitteln <SEP> und
<tb> ,der <SEP> Einwirkung <SEP> von <SEP> p-Chl#or-benzoylelilorid
<tb> unterwirft.
<tb>
Gegenstand <SEP> vorliegenden <SEP> Patentes <SEP> ist <SEP> nun
<tb> ein <SEP> Verfahren <SEP> zur <SEP> Herstellung <SEP> ein-es <SEP> ähnli chen <SEP> Farbstoffes. <SEP> Es <SEP> ist <SEP> daduroli <SEP> gekenn Zelichnet, <SEP> dass <SEP> man <SEP> 4-Amin-o-I-[6'-chlor-l' earboxy-2'-a,uilid,o,]-a.nth,rachinon, <SEP> ein <SEP> den
<tb> Aeridonringsohluss <SEP> bewirkendes <SEP> Mittel <SEP> und
<tb> Isop'hthaloyleblorid <SEP> aufeinander <SEP> einwirken
<tb> lasst. <SEP> Zvoeekmüss#ig <SEP> arbeitet- <SEP> man <SEP> inder <SEP> Weise,
<tb> dass <SEP> man,durüh <SEP> Einwirkung <SEP> von <SEP> Chlorsulfon saure <SEP> zunächstdie <SEP> Bildung <SEP> des <SEP> Aexidonringes
<tb> vornimmt <SEP> und <SEP> anschliessend <SEP> IsopUthaloyl ohl(>HU <SEP> einwirken <SEP> lässt.
<SEP> Der <SEP> so <SEP> erhaltene
<tb> Farbstoff <SEP> stellt <SEP> ein <SEP> blaues <SEP> Pulver <SEP> -dar. <SEP> Er
EMI0001.0005
färbt <SEP> aus <SEP> rotvioletter <SEP> <B>Kape</B> <SEP> die <SEP> Faser <SEP> leb haft <SEP> blau. <SEP> Die <SEP> Färbungen <SEP> sind <SEP> sehr <SEP> gut
<tb> chlor- <SEP> und <SEP> kochecht.
<tb>
<I>Beispiel:</I>
<tb> <B>10</B> <SEP> Gewiplits-Leiled-es <SEP> 4-Amino-I-[6'-chlor l'-carboxy-2'-anilidol-antlirachinons <SEP> der <SEP> nach stehenden <SEP> Formel
EMI0001.0006
wer-den bei Zimmertemperatur in die 10fache Menge Cblorsulfonsäure eingetragen. und zirka 2 Stunden auf<B>30'</B> erwärmt. Die braune Lösung wird auf Ei4s gegeben. Der ab- cl cl geschiedene Farbstoff wird abgesaugt. ge- wasehen und getrocknet.
Zur Aroylierung werden<B>37,5</B> Gewiehts- teile des fein gepulverten Farbstoffes mit 1.0,2 Gewielitsteilen Is#ophthaioylehlori,d in <B>800</B> Gewiehtsteilen Nitrobenzol zum Sieden .erhit#zt, wobei der Farbstoff mit blauer Farbe teilweise in Lösurig gelit. Beim Abkühlen scheidet -sieh der aroylierte, Farbstoff als blaues Pulver aus.
Er färbt aus violetter Küpv" die Faser lebhaft blau. Die Färbungen besitzen eine sehr gute. Chlor- und Korh- echtheit.
Process for the production of a nub dye of the Anthraeliinonaeridoureibe.
EMI0001.0004
The subject <SEP> of the <SEP> main patent <SEP> is <SEP> a
<tb> Process <SEP> for the <SEP> production <SEP> of a <SEP> coarse-grained substance <SEP>: the <SEP> anthrar, hinenaeridon range, <SEP> nails
<tb> which <SEP> one <SEP> 4-amino-3-, sulfo-I- [6'-chloro l'-carboxy-29'-an, illdol-a.nthrar, hinon <SEP> in <SEP > belie bi, c., er <SEP> sequence <SEP> of <SEP> action <SEP> of <SEP> den
<tb> Aeri, do, n, rin "o" conclusion <SEP> effecting <SEP> means <SEP> and
<tb>, the <SEP> action <SEP> of <SEP> p-Chl # or-benzoylelilorid
<tb> subject.
<tb>
The subject of <SEP> of the present <SEP> patent <SEP> is <SEP> now
<tb> a <SEP> process <SEP> for <SEP> production <SEP> a <SEP> similar <SEP> dye. <SEP> Es <SEP> is <SEP> daduroli <SEP> marked Zelichnet, <SEP> that <SEP> man <SEP> 4-amine-oI- [6'-chlor-l 'earboxy-2'-a, uilid, o,] - a.nth, rachinon, <SEP> a <SEP> den
<tb> Aeridonringsohluss <SEP> effecting <SEP> agent <SEP> and
<tb> Isop'hthaloyleblorid <SEP> act on each other <SEP>
<tb> let. <SEP> Zvoeekmüss # ig <SEP> works- <SEP> man <SEP> in the <SEP> way,
<tb> that <SEP>, by <SEP> action <SEP> of <SEP> chlorosulfonic acid <SEP>, first the <SEP> formation <SEP> of the <SEP> aexidone ring
<tb> performs <SEP> and <SEP> then <SEP> IsopUthaloyl ohl (> HU <SEP> lets <SEP> take effect.
<SEP> The <SEP> so <SEP> received
<tb> Dye <SEP> represents <SEP> a <SEP> blue <SEP> powder <SEP> -. <SEP> He
EMI0001.0005
<SEP> from <SEP> red-violet <SEP> <B> cap </B> <SEP> colors the <SEP> fiber <SEP> vivid <SEP> blue. <SEP> The <SEP> colors <SEP> are <SEP> very <SEP> good
<tb> chlorine- <SEP> and <SEP> boil-proof.
<tb>
<I> Example: </I>
<tb> <B> 10 </B> <SEP> Gewiplits-Leiled-es <SEP> 4-Amino-I- [6'-chloro l'-carboxy-2'-anilidol-antlirachinons <SEP> from <SEP > according to the <SEP> formula below
EMI0001.0006
are entered into 10 times the amount of chlorosulfonic acid at room temperature. and heated to <B> 30 '</B> for about 2 hours. The brown solution is added to egg. The dyestuff which has separated out is filtered off with suction. washed and dried.
For aroylation, 37.5 parts by weight of the finely powdered dye are mixed with 1.0.2 parts by weight of Is # ophthaioylehlori, d in <B> 800 </B> parts by weight of nitrobenzene to boiling, with the Dye with blue color partially gelit in solution. When cooling, the aroylated dye separates out as a blue powder.
He dyes the fiber vividly blue from violet Küpv ". The dyeings have very good fastness to chlorine and korh.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201529X | 1936-03-04 | ||
| CH197586T | 1937-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201529A true CH201529A (en) | 1938-11-30 |
Family
ID=25723019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201529D CH201529A (en) | 1936-03-04 | 1937-02-25 | Process for the production of a vat dye of the anthraquinone acridone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201529A (en) |
-
1937
- 1937-02-25 CH CH201529D patent/CH201529A/en unknown
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