CH261860A - Process for the preparation of a vivid acid dye of the anthraquinone series. - Google Patents
Process for the preparation of a vivid acid dye of the anthraquinone series.Info
- Publication number
- CH261860A CH261860A CH261860DA CH261860A CH 261860 A CH261860 A CH 261860A CH 261860D A CH261860D A CH 261860DA CH 261860 A CH261860 A CH 261860A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- sulfuric acid
- dye
- preparation
- amino
- Prior art date
Links
- 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 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000980 acid dye Substances 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ASKDWVZYNOOCIP-UHFFFAOYSA-N 2,4,6-trimethylcyclohexan-1-amine Chemical compound CC1CC(C)C(N)C(C)C1 ASKDWVZYNOOCIP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JEPVBIMOJDNAAK-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid;sodium Chemical compound [Na].O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC(S(O)(=O)=O)=C2N JEPVBIMOJDNAAK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003756 stirring 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
- C09B1/303—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 255968. <B>Verfahren</B> zur <B>Herstellung eines</B> lebhaften sauren Farbstoffes <B>der</B> Anthrachinonreihe. Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines neuen sauren Farbstoffes der Anthrachinonreihe und ist dadurch gekennzeichnet, dass man 1-Amino-4- bromanhtrachinon-2-sulfonsäure mit 1-Amino- 2,4,6-trimethylcyclohexan kondensiert.
<I>Beispiel:</I> 8,1 Teile 1-amino-4-bromanthrachinon-2- sulfonsaures Natrium, 40 Teile 1-Amino-2,4,6- trimethylcyclohexan, 4 Teile Natronlauge 30 %, 0,1 Teil Kupferpulver, 0,1 Teil Kupfer- chlorür und 120 Teile Wasser werden unter Rühren und Einleiten eines mässigen Stick stoffstromes so lange auf 60 bis<B>800</B> erhitzt, bis die Masse blau geworden ist. Das Konden sationsprodukt wird auf übliche Weise auf gearbeitet. Der Farbstoff ist ein blaues Pul ver, das sich in kaltem Wasser ziemlich leicht mit blauer Farbe löst. Seine Lösungsfarbe in konzentrierter Schwefelsäure ist hellgelb.
Beim Zusatz von Paraformaldehyd zur schwe felsauren Lösung tritt ein Farbumschlag nach klar grünstichig Blau ein.
Der Farbstoff färbt tierische und künst liche Fasern von der Art der Nylonfaser in lebhaften reinblauen Tönen von guten Nass- echtheiten und mit sehr gleichmässigem Auf ziehvermögen sowohl im neutralen als auch im essig- und schwefelsauren Bade.
Additional patent to main patent no. 255968. <B> Process </B> for <B> production </B> of a </B> lively acidic dye <B> of the </B> anthraquinone series. The present patent relates to a process for the preparation of a new acidic dye of the anthraquinone series and is characterized in that 1-amino-4-bromanhtrachinone-2-sulfonic acid is condensed with 1-amino-2,4,6-trimethylcyclohexane.
<I> Example: </I> 8.1 parts of 1-amino-4-bromoanthraquinone-2-sulfonic acid sodium, 40 parts of 1-amino-2,4,6-trimethylcyclohexane, 4 parts of 30% sodium hydroxide solution, 0.1 part Copper powder, 0.1 part of copper chloride and 120 parts of water are heated to 60 to <B> 800 </B> with stirring and introduction of a moderate stream of nitrogen until the mass has turned blue. The condensation product is worked on in the usual way. The dye is a blue powder that dissolves with a blue color fairly easily in cold water. Its solution color in concentrated sulfuric acid is light yellow.
When paraformaldehyde is added to the sulfuric acid solution, the color changes to a clear greenish blue.
The dye dyes animal and artificial fibers like nylon fibers in lively, pure blue tones with good wet fastness properties and very even absorption in neutral baths as well as in acetic and sulfuric acid baths.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261860T | 1946-07-05 | ||
| CH255968T | 1946-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261860A true CH261860A (en) | 1949-05-31 |
Family
ID=25729944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261860D CH261860A (en) | 1946-07-05 | 1946-07-05 | Process for the preparation of a vivid acid dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261860A (en) |
-
1946
- 1946-07-05 CH CH261860D patent/CH261860A/en unknown
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