CH116079A - Process for the preparation of a vat dye of the anthraquinone series. - Google Patents
Process for the preparation of a vat dye of the anthraquinone series.Info
- Publication number
- CH116079A CH116079A CH116079DA CH116079A CH 116079 A CH116079 A CH 116079A CH 116079D A CH116079D A CH 116079DA CH 116079 A CH116079 A CH 116079A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid
- yellow
- vat dye
- anthraquinone series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 description 2
- 150000004056 anthraquinones Chemical class 0.000 title description 2
- 239000000984 vat dye Substances 0.000 title description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PLGPRGMWHYWEFT-UHFFFAOYSA-N 2-amino-1-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(N)=CC=C3C(=O)C2=C1 PLGPRGMWHYWEFT-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000012991 xanthate 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
- C09B5/32—1.3 azoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines güpenfar bstoües der Anthrachinonreihe. Im Hauptpatent Nr. 101169 ist ein Ver fahren zur Darstellung eines wertvollen gel ben Iiüpenfarbstoffes beschrieben, nach dem man auf 1-Merkapio-2-aminoanthrachinon ein solches Derivat der Terephthalsäure einwir ken lässt, das leicht in die Terephthalsäure überführbar ist, wie zum Beispiel die Säure halogenide, die entsprechenden (v-Tetra. be ziehungsweise Halogenmethylderivate,
den Dialdehyd etc. Nach dem ersten Zusatz patent vom gleichen Tage gelangt man zu dem gleichen Farbstoff, wenn. man 1-Halo- gen-2-amino-,Lnthrachinon verwendet, und das zunächst erhaltene Zwischenprodukt mit einer Schwefel abgebenden Substanz, z. B. Schwefel, Schwefelnatrium, Natriumpolysul- fid, Isaliumxanthogenat etc. behandelt. Man kann dabei in Gegenwart von Kondensations mitteln arbeiten.
Es wurde nun gefun-len, dass man einen neuen, Baumwolle in kräftig orangegelben Tönen färbenden, halogenfreien Küpenfarb- stoff erhält, wenn man auf 1-Halogen-2- aminoanthrachinon Adipinsäure, in Form eines Derivats, das in die Säure überführba.r ist, einwirken lässt und das zunächst ent standene Produkt mit einer Schwefel ab gebenden Substanz behandelt.
<I>Beispiel:</I> 10 Teile des Einwirkungsproduktes von 1 Mol. @Adipinsäurechlorid auf 2 Mol. 1- Chlor-2-aminoanthrachinon, 20 Teile wasser freies Schwefelnatrium, 20 Teile Schwefel und 100 Teile Phenol werden unter Rühren 6 bis 7 Stunden auf 170.' erhitzt,
worauf das Reaktionsprodukt bei 70 bis<B>80</B> abge saugt und mit etwas Phenol und Wasser ge waschen wird. Man kann den Farbstoff ge- wünschtenfalls durch Behandlung mit alka lischer Hypochloritlösung oder durch Um kristallisieren aus Schwefelsäure einer beson deren Reinigung unterziehen. Er stellt ein orangegelbes Pulver dar, das sich) in kon zentrierter Schwefelsäure mit gelber Farbe löst. Die Lösung in alkalischem Hydrosulfit ist violett, die Färbung auf Baumwolle kräf tig orangegelb.
Process for the preparation of a grade dye of the anthraquinone series. In the main patent no. 101169 a process is described for the preparation of a valuable yellow ben Iüpenfarerstoffes, according to which one can act on 1-mercapio-2-aminoanthraquinone such a derivative of terephthalic acid that can easily be converted into terephthalic acid, such as, for example Acid halides, the corresponding (v-tetra. Or halomethyl derivatives,
the dialdehyde etc. After the first addition patent of the same day one arrives at the same dye, if. one uses 1-halogen-2-amino-, Lnthraquinone, and the intermediate product initially obtained with a sulfur-releasing substance, eg. B. sulfur, sulfur sodium, sodium polysulphide, isalium xanthate, etc. treated. You can work in the presence of condensation agents.
It has now been found that a new halogen-free vat dye which dyes cotton in strong orange-yellow tones is obtained when 1-halo-2-aminoanthraquinone adipic acid, in the form of a derivative that can be converted into the acid, is obtained , allows it to take effect and treats the initially created product with a sulfur-releasing substance.
<I> Example: </I> 10 parts of the action product from 1 mol. @ Adipic acid chloride to 2 mol. 1- chloro-2-aminoanthraquinone, 20 parts anhydrous sodium sulphide, 20 parts sulfur and 100 parts phenol are mixed 6 to 7 Hours to 170. ' heated,
whereupon the reaction product is sucked off at 70 to 80 and washed with a little phenol and water. The dye can, if desired, be subjected to a special purification by treatment with alkaline hypochlorite solution or by recrystallizing from sulfuric acid. It is an orange-yellow powder that dissolves in concentrated sulfuric acid with a yellow color. The solution in alkaline hydrosulphite is violet, the color on cotton is a strong orange-yellow.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH116079T | 1925-02-03 | ||
| CH101169T | 1925-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH116079A true CH116079A (en) | 1926-08-02 |
Family
ID=25705957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH116079D CH116079A (en) | 1925-02-03 | 1925-02-03 | Process for the preparation of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH116079A (en) |
-
1925
- 1925-02-03 CH CH116079D patent/CH116079A/en unknown
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