DE152661C - - Google Patents
Info
- Publication number
- DE152661C DE152661C DE1903152661D DE152661DA DE152661C DE 152661 C DE152661 C DE 152661C DE 1903152661 D DE1903152661 D DE 1903152661D DE 152661D A DE152661D A DE 152661DA DE 152661 C DE152661 C DE 152661C
- Authority
- DE
- Germany
- Prior art keywords
- red
- naphthol
- acid
- parts
- bluish
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 230000001808 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 10
- 239000002966 varnish Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- 229910052601 baryte Inorganic materials 0.000 description 4
- 239000010428 baryte Substances 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 3
- 229950011260 betanaphthol Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 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
- 230000002378 acidificating Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- -1 naphthol sulfonic acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
PATENTAMT.PATENT OFFICE.
Λ! 152661 KLASSE 22a., */ Λ! 152661 CLASS 22a., * /
Es wurde gefunden, daß die durch Kuppeln von diazotierten α-Amidoanthrachinonen mit Naphtholsulfosäuren erhältlichen Azofarbstoffe sehr wertvolle Eigenschaften haben. Insbesondere zeichnen sich dieselben dadurch aus, daß sie beim Fällen mit den üblichen lackbildenden Agenden sehr lichtechte und schöne Lacke liefern. Die Nuancen der neuen Farbstoffe variieren im allgemeinen von Gelbrot ίο bis Blaurot.It has been found that the coupling of diazotized α-amidoanthraquinones with Naphtholsulfonic acids available azo dyes have very valuable properties. In particular they are characterized by the fact that they are formed when felling with the usual lacquer-forming Deliver agendas very lightfast and beautiful varnishes. The nuances of the new dyes generally vary from yellow-red ίο to blue-red.
Farbstoff aus α - Amidoanthrachinon und 2'6'8-Naphtholdisulfosäure.Dye from α - amidoanthraquinone and 2'6'8-naphthol disulfonic acid.
22,3 Teile a-Amidoanthrachinon werden in möglichst fein verteilter Form in 300 Teilen Wasser suspendiert und unter guter Kühlung mittels 7 Teilen Nitrit und 40 Teilen Salzsäure von 2O° Be. diazotiert. Die so erhaltene Diazoverbindung läßt man unter gutem Umrühren langsam in eine mit überschüssiger Soda versetzte Lösung von 32 Teilen 2·6·8-Naphtholdisulfosäure einfließen. Nach etwa 12 stündigem Rühren wird kurze Zeit auf etwa 70 ° erwärmt und der gebildete Farbstoff ausgesalzen. Derselbe liefert auf Wolle in saurem Bade gelbstichig rote Töne. Der Tonerde-Barytlack zeigt eine lebhafte rote Nuance von sehr großer Lichtechtheit.22.3 parts of a-amidoanthraquinone are in finely divided form suspended in 300 parts of water and with good cooling by means of 7 parts of nitrite and 40 parts of hydrochloric acid of 20 ° Be. diazotized. The thus obtained Diazo compound is slowly poured into one with excess with thorough stirring Soda-added solution of 32 parts of 2x6x8-naphthol disulfonic acid is poured in. After about Stirring for 12 hours is briefly heated to about 70 ° and the dye formed salted out. It produces yellowish red tones on wool in an acidic bath. Of the Alumina-barite varnish shows a lively red shade of very high lightfastness.
Farbstoff aus 1 • 8-Diamidoanthrachinon und 2 · 8 - Naphtholsulf osäure.Dye from 1 • 8-diamidoanthraquinone and 2 • 8 - naphtholsulfonic acid.
24 Teile ι · 8-Diamidoanthrachinon werden in der in Beispiel 1 beschriebenen Weise mit 14 Teilen Nitrit und 80 Teilen Salzsäure von 20° Be. diazotiert. Die so gebildete Tetrazoverbindung läßt man unter gutem Umrühren in eine mit überschüssiger Soda versetzte Lösung" von 48 Teilen 2 · 8-Naphtholmonosulfosäure einfließen. Die weitere Behandlung und Isolierung des gebildeten Tetrazofarbstoffes erfolgt in der in Beispiel 1 angegebenen Weise. Der Farbstoff färbt Wolle in saurem Bade blaustichig rot. Der Tonerde-Barytlack zeigt eine sehr blaustichige und lichtechte Nuance.24 parts of ι · 8-diamidoanthraquinone are in the manner described in Example 1 with 14 parts of nitrite and 80 parts of hydrochloric acid 20 ° Be. diazotized. The tetrazo compound thus formed is left with thorough stirring in a "solution" of 48 parts of 2 × 8-naphthol monosulfonic acid mixed with excess soda flow in. The further treatment and isolation of the tetrazo dye formed takes place in the manner indicated in Example 1. The dye dyes wool in an acid bath bluish red. The alumina-barite varnish shows a very bluish and lightfast shade.
In analoger Weise verfährt man bei Verwendung anderer a-Amidoanthrachinone bezw. anderer Naphtholsulfosäuren.The procedure is analogous when using other a-amidoanthraquinones BEZW. other naphthol sulfonic acids.
In folgender Tabelle sind die Nuancen einer Reihe der nach unserem Verfahren erhältlichen Farbstoffe angeführt.In the table below are the nuances of a number of those available through our process Dyes listed.
Farbstoffaus: *Dye from: *
l-Naphthol-4-sulfosäure l-naphthol-4-sulfonic acid
i-Naphthol-3 · 6-disulfosäure i-Naphthol-3 · 8-disulfosäure . . 2-Naphthol-6 · 8-disulfosäure . . 2-Naphthol"3 · 6-disulfosäure . . 2-Naphthol"3 · 6 · 8-trisulfosäure Färbt Wollei-naphthol-3 x 6-disulfonic acid i-naphthol-3 x 8-disulfonic acid. . 2-naphthol-6x8-disulfonic acid. . 2-naphthol "3x6-disulfonic acid.. 2-Naphthol "3x6x8-trisulfonic acid dyes wool
Tonerde-BarytlackAlumina-barite varnish
a-Amidoanthrachinon α-amidoanthraquinone
blaustichig rot
gelbstichig rot
blaustichig rot
gelbstichig rot
blaustichig rot
rotbluish red
yellowish red
bluish red
yellowish red
bluish red
Red
blaustichig rot
blaurot
blaurot .bluish red
blue red
blue red .
rotRed
blaustichig rot
rotbluish red
Red
Farbstoffaus:Dye from:
I-Naphthol-4-sulfosäure I-naphthol-4-sulfonic acid
2-Naphthol"3 · 6-disulfosäure . . . 2-Naphthol-5 · 7-disulfosäure. .. 2-Naphthol-3 · 6 · 8-trisulfosäure2-naphthol "3 · 6-disulfonic acid... 2-naphthol-5 · 7-disulfonic acid. .. 2-naphthol-3x6x8-trisulfonic acid
i-Naphthol-3 · 8-disulfosäure .. .i-naphthol-3 · 8-disulfonic acid ...
2-Naphthol-8-sulfosäure. 2-naphthol-8-sulfonic acid.
2-Naphthol-3 · 6 · 8-trisulfosäure Färbt Wolle2-Naphthol-3 · 6 · 8-trisulfonic acid dyes wool
Tonerde-BarytlackAlumina-barite varnish
7·
8.7 ·
8th.
9-9-
10.10.
II. 12.II. 12th
13·13 ·
ι · 5-Diamidoanthrachinon ι · 5-diamidoanthraquinone
ι • S-Diamidoanthrachinon ι • S-diamido anthraquinone
blaurot
blaurotblue red
blue red
blaustichig rot
bordeauxrotbluish red
burgundy
braunrotbrownish red
blaustichig rotbluish red
rotRed
blaurotblue red
blaurotblue red
. blaurot. blue red
bordeauxrotburgundy
braunrotbrownish red
blaurotblue red
rot.Red.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT20697D AT20697B (en) | 1903-05-15 | 1904-05-24 | Process for the preparation of azo dyes from α-amidoanthraquinones. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE152661C true DE152661C (en) |
Family
ID=419368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1903152661D Expired - Lifetime DE152661C (en) | 1903-05-15 | 1903-05-15 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE152661C (en) |
-
1903
- 1903-05-15 DE DE1903152661D patent/DE152661C/de not_active Expired - Lifetime
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