DE250240C - - Google Patents
Info
- Publication number
- DE250240C DE250240C DENDAT250240D DE250240DA DE250240C DE 250240 C DE250240 C DE 250240C DE NDAT250240 D DENDAT250240 D DE NDAT250240D DE 250240D A DE250240D A DE 250240DA DE 250240 C DE250240 C DE 250240C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- black
- dyes
- toluidine
- aminophenyltrimethylammonium
- 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.)
- Active
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- -1 trimethylammonium phenylazo-m-toluidine Chemical compound 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JJQUYMQFKHXRNE-UHFFFAOYSA-N NC[N+](C)(C)C1=CC=CC=C1 Chemical compound NC[N+](C)(C)C1=CC=CC=C1 JJQUYMQFKHXRNE-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920002955 Art silk Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
- C09B44/04—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing amino as the only directing group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERtTCHESKAISERtTCHES
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 250240 — KLASSE 22a. GRUPPE- M 250240 - CLASS 22a. GROUP
In den Patentschriften 95530, 98585, 100420, 109491 der Kl. 22 a werden basische sekundäre Disazofarbstoffe beschrieben, welche in Anfangsstellung Aminophenyltrimethylammonium, in Mittelstellung primäre Amine, in Endstellung Amine und Phenole enthalten. Unter den vielen beschriebenen Kombinationen ist keine, welche die Faser schwarz färbt. Es sind derartige schwarze basische Disazofarbstoffe bisher überhaupt nicht bekannt.In patents 95530, 98585, 100420, 109491 of class 22 a, basic secondary disazo dyes are described, which in the initial position Aminophenyltrimethylammonium, in the middle position primary amines, in the end position Contain amines and phenols. Among the many combinations described, there is none that will color the fiber black. It such black basic disazo dyes are not yet known at all.
Es wurde nun gefunden, daß die Kombination Aminophenyltrimethylammonium — > m-Toluidin —> 1 · 8-Diaminonapthalin ein Farbstoff ist, welcher sehr schöne und waschechte schwarze Färbungen liefert, die namentlich für Kunstseide von hohem Werte sind. Das war nicht vorauszusehen. Bei analog zusammengesetzten Säurefarbstoffen von der allgemeinen Konstitution Benzolderivat —->- Benzolderivat —> Naphtalinderivat erzielte man rote, bei Anhäufung auxochromer Gruppen im endständigen Naphtalinrest höchstens violette Nuancen. Der in der Patentschrift 109491 beschriebene Farbstoff Aminophenyltrimethylammonium —ν Aminohydrochinondimethyläther >, ι · 5-Aminonaphtol unterscheidet sich von dem Farbstoff der vorliegenden Erfindung wesentlich dadurch, daß er, trotzdem in Mittelstellung der viel mehr auxochrome Gruppen tragende Hydrochinonäther steht, nur blaue Färbungen liefert, während schon 1 prozentige Färbungen des Farbstoffes der vorliegenden 35 It has now been found that the combination aminophenyltrimethylammonium -> m-toluidine -> 1 · 8-diaminonapthalene is a dye which gives very beautiful and washfast black colorations which are particularly valuable for rayon. That was not to be foreseen. In the case of acid dyes with an analogous composition and of the general constitution benzene derivative -> - benzene derivative -> naphthalene derivative, red shades were obtained; if auxochromic groups were accumulated in the terminal naphthalene residue, at most violet shades were obtained. The dye aminophenyltrimethylammonium -ν Aminohydroquinondimethyläther>, ι · 5-aminonaphtol described in patent specification 109491 differs from the dye of the present invention essentially in that it, despite being in the middle position of the hydroquinone ether, which carries much more auxochromic groups, only gives blue colorations, while already 1 percent coloration of the dye of the present 35
4040
4545
Erfindung tief schwarz sind. Bei Verwendung von m-Diaminen in Endstellung werden nur braune Nuancen erhalten.Invention are deep black. When using m-diamines in the end position only brown nuances preserved.
Durch die Herstellung des neuen Farbstoffes wird einem technischen Bedürfnis abgeholfen insofern, als noch kein Farbstoff existiert, der Kunstseide in neutralem oder saurem Bade, also mit möglichster Schonung der Faser, schwarz färbt. Es wird demnach durch das Verfahren ein wesentlicher gewerblicher Fortschritt erzielt.The manufacture of the new dye remedies a technical need insofar as no dye exists yet, the artificial silk in a neutral or acid bath, So with the greatest possible protection of the fiber, dyes black. It is therefore made by the Process achieved significant commercial progress.
34 kg salzsäures Trimethylammoniumphenylazo-m-toluidin werden in etwa 1500 1 Wasser gelöst, mit 24 kg Salzsäure (190 Be.) und 6,9 kg Natriumnitrit diazotiert. Die Diazolösung läßt man in eine gekühlte Lösung von 16 kg 1 · 8-Diaminonaphtalin in 24 kg Salzsäure (190Be.) und etwa 6001 Wasser einlaufen.34 kg of hydrochloric acid trimethylammonium phenylazo-m-toluidine are dissolved in about 1500 l of water and diazotized with 24 kg of hydrochloric acid (19 0 Be.) And 6.9 kg of sodium nitrite. The diazo solution is allowed to run into a cooled solution of 16 kg of 1 × 8-diaminonaphthalene in 24 kg of hydrochloric acid (19 0 Be.) And about 600 liters of water.
Nach längerem Rühren wird auf etwa 500 angewärmt und durch Zusatz von Kochsalzlösung ausgesalzen. Getrocknet, bildet der Farbstoff ein schwarzes Pulver. Er färbt auf Kunstseide ein schönes Blauviolettschwarz.After prolonged stirring, is heated to about 50 0 and salted out by the addition of brine. When dried, the dye forms a black powder. He dyes a beautiful blue-violet-black on artificial silk.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE250240C true DE250240C (en) |
Family
ID=508787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT250240D Active DE250240C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE250240C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1054616B (en) * | 1954-05-03 | 1959-04-09 | Du Pont | Process for the production of monoazo dyes coloring polyacrylonitrile fibers |
-
0
- DE DENDAT250240D patent/DE250240C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1054616B (en) * | 1954-05-03 | 1959-04-09 | Du Pont | Process for the production of monoazo dyes coloring polyacrylonitrile fibers |
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