CH261864A - Process for the preparation of a vivid acidic leveling dye of the anthraquinone series. - Google Patents
Process for the preparation of a vivid acidic leveling dye of the anthraquinone series.Info
- Publication number
- CH261864A CH261864A CH261864DA CH261864A CH 261864 A CH261864 A CH 261864A CH 261864D A CH261864D A CH 261864DA CH 261864 A CH261864 A CH 261864A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- vivid
- blue
- good
- anthraquinone series
- Prior art date
Links
- 230000002378 acidificating effect Effects 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 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 8
- -1 alkali metal sulfite Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- UASJEBYKRVLBPP-UHFFFAOYSA-N NC1=C(C=C(C=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O)Br)Br Chemical compound NC1=C(C=C(C=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O)Br)Br UASJEBYKRVLBPP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 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
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- ASKDWVZYNOOCIP-UHFFFAOYSA-N 2,4,6-trimethylcyclohexan-1-amine Chemical compound CC1CC(C)C(N)C(C)C1 ASKDWVZYNOOCIP-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
Verfahren zur Herstellung eines lebhaften sauren Egalisierungsfarbstoffes der Anthrachinonreihe. Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines lebhaften sauren Egalisierungsfarbstoffes der Anthrachinon- reihe und ist dadurch gekennzeichnet, dass man 1-Amiiio-2,4-dibromanthrachinon-5-sulfo- säure mit 1-Aniino-2,4,6-trimethyleyclohexan kondensiert und das erhaltene Zwischenpro dukt mit einem Alkalimetallsulfit erhitzt.
<I>Beispiel:</I> 10,4 Teile 1-amino-2,4-dibromanthrachinon- 5-sulfonsaures Kalium, 20 Teile 1-Ainino-2,4,6- trimethyleyclohexan, 4 Teile Natronlauge 30 %, 0,3 Teile Kupferpulver und 120 Teile Wasser werden während 2.1 Stunden unter Einleiten eines mässigen Stickstoffstromes auf 60 bis 700 erhitzt, das Reaktionsprodukt hierauf der Behandlung mit Sulfit unter ge eigneten Bedingungen unterworfen und da durch das zweiständige Bromatom durch eine Sulfogruppe ersetzt.
Man erhält ein blaues Farbstoffpulver, das sich in kaltem Wasser leicht mit leuchtend grünstichig blauer Farbe löst. In konzentrierter Schwefelsäure löst es sich farblos; beim Zusatz von wenig Para- formaldehyd tritt ein Farbumschlag nach rot- stiehig blau ein. Der Farbstoff färbt tierische Fasern, wie Wolle, Seide usw., sowie künstliche Fasern, z. B. Nylon, in lebhaften reinblauen Tönen von guter Lichtechtheit, guten Nassechtheiten und ist von gutem Egalisierungsvermögen.
Process for the preparation of a vivid acidic leveling dye of the anthraquinone series. The present patent relates to a process for the production of a lively acidic leveling dye of the anthraquinone series and is characterized in that 1-amino-2,4-dibromoanthraquinone-5-sulfonic acid is combined with 1-aniino-2,4,6- trimethyleyclohexane condenses and the intermediate product obtained is heated with an alkali metal sulfite.
<I> Example: </I> 10.4 parts of 1-amino-2,4-dibromoanthraquinone-5-sulfonic acid potassium, 20 parts of 1-amino-2,4,6-trimethyleyclohexane, 4 parts of sodium hydroxide solution 30%, 0, 3 parts of copper powder and 120 parts of water are heated to 60 to 700 for 2.1 hours while passing in a moderate stream of nitrogen, the reaction product is then subjected to treatment with sulfite under suitable conditions and then replaced by the two-position bromine atom with a sulfo group.
A blue dye powder is obtained which easily dissolves in cold water with a bright greenish blue color. It dissolves colorless in concentrated sulfuric acid; if a little paraformaldehyde is added, the color changes to reddish blue. The dye dyes animal fibers such as wool, silk, etc., as well as artificial fibers, e.g. B. nylon, in vivid, pure blue tones of good lightfastness, good wet fastness and is of good leveling power.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH261864T | 1946-07-05 | ||
| CH255969T | 1946-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261864A true CH261864A (en) | 1949-05-31 |
Family
ID=25729951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261864D CH261864A (en) | 1946-07-05 | 1946-07-05 | Process for the preparation of a vivid acidic leveling dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261864A (en) |
-
1946
- 1946-07-05 CH CH261864D patent/CH261864A/en unknown
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