DE258654C - - Google Patents
Info
- Publication number
- DE258654C DE258654C DENDAT258654D DE258654DA DE258654C DE 258654 C DE258654 C DE 258654C DE NDAT258654 D DENDAT258654 D DE NDAT258654D DE 258654D A DE258654D A DE 258654DA DE 258654 C DE258654 C DE 258654C
- Authority
- DE
- Germany
- Prior art keywords
- red
- acid
- diazo compounds
- dyes
- contain
- 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
- 239000000975 dye Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 150000008049 diazo compounds Chemical class 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-Xylidine Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 3
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-Xylidine Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-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
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Durch Patent 256999 ist ein Verfahren zur Darstellung besonders zur Pigmentfarbenbereitung geeigneter Monoazofarbstoffe geschützt, welches darin besteht, daß man solche Diazoverbindungen der Benzolreihe, welche mindestens eine von der Sulfogruppe verschiedene negative Gruppe enthalten, mit den Arylamiden' der 2 · 3-Oxynaphtoesäure kombiniert. Die so erhaltenen Farbstoffe sind ölunlöslich.Patent 256999 provides a method of representation especially for pigment color preparation Protected suitable monoazo dyes, which consists in the fact that one such diazo compounds the benzene series, which contain at least one negative group different from the sulfo group, with the arylamides' of 2 x 3-oxynaphtoic acid combined. The dyes obtained in this way are insoluble in oil.
Solche Kombinationen aus Diazoverbindungen der Benzolreihe und 2 · 3-Oxynaphtoesäurearylamiden, welche weder im Diazorest noch in der Arylamidgruppe ein negatives Radikal enthalten, sind öllöslich. Es wurde nun gefun den, daß Farbstoffe von wesentlich erhöhter ölechtheit erhalten werden, wenn man Diazoverbindungen der Benzolreihe, welche keine negative Gruppe enthalten, mit solchen 2 · 3 - Oxynaphtoesäurearylamiden kombiniert, welche im Arylrest mindestens eine von der Sulfogruppe verschiedene negative Gruppe, wie Cl oder NO2, enthalten. Hierbei ist die Wirkung in bezug auf Verminderung der öllöslichkeit bei Chloratom pn, welche in meta-Stellung zur Imidgruppe sich befinden, am geringsten. Ortho- oder para-ständiges Chloratom übt einen größeren Einfluß aus.Such combinations of diazo compounds of the benzene series and 2x3-oxynaphthoic acid arylamides, which contain a negative radical neither in the diazo radical nor in the arylamide group, are oil-soluble. It has now been found that dyes of significantly increased oiliness are obtained if diazo compounds of the benzene series which do not contain a negative group are combined with those 2 · 3 - oxynaphthoic arylamides which have at least one negative group different from the sulfo group in the aryl radical, such as Cl or NO 2 . Here, the effect in terms of reducing the oil solubility is lowest with chlorine atoms pn, which are in the meta position to the imide group. Ortho or para chlorine atom has a greater influence.
Lackazofarbstoffe, von ähnlicher ölunlöslichkeit wie die vorliegenden, welche keine Sulfo- oder Carboxylgruppen und auf der Diazoseite des Farbstoffmoleküls keine negative Gruppe enthalten, sind bis jetzt noch nicht bekannt. Die Darstellung der Farbstoffe kann in saurer, neutraler oder alkalischer Lösung vorgenommen werden.Lackazo dyes, of similar oil insolubility like the present ones, which have no sulfo or carboxyl groups and on the diazo side of the dye molecule do not contain a negative group are not yet known. The representation of the dyes can be done in acidic, neutral or alkaline solution will.
12,1 Teile m-Xylidin werden mit 28,5 Teilen Salzsäure 200Be. und 6,9 Teilen Natriumnitrit in üblicher Weise diazotiert und die so erhaltene Diazoverbindung unter gutem Rühren in eine wässerige Suspension von 34,8 Teilen 2 · 3 - Oxy naphtoesäure - 2 · 5 - dichloranilid, bereitet durch Auflösen desselben in verdünnter Natronlauge und Ausfällen mit verdünnter Salzsäure unter Zusatz von Türkischrotöl, der noch 15,9 Teile kalzinierte Soda zugesetzt waren, einlaufen gelassen. Der Farbstoff scheidet sich in tiefroten Flocken aus, er wird nach Vollendung der Kombination abfiltriert, neutral gewaschen und vorteilhaft in Pastenform verwendet. Nach dem Trocknen bildet er ein blaustichig bordeaux Pulver und löst sich in konzentrierter Schwefelsäure mit tief blaustichig roter Farbe.12.1 parts of m-xylidine with 28.5 parts of hydrochloric acid 20 0 Be. and 6.9 parts of sodium nitrite are diazotized in the usual way and the diazo compound thus obtained is mixed with vigorous stirring in an aqueous suspension of 34.8 parts of 2 · 3 - oxynaphthoic acid - 2 · 5 - dichloroanilide, prepared by dissolving it in dilute sodium hydroxide solution and precipitating it Dilute hydrochloric acid with the addition of Turkish red oil to which 15.9 parts of calcined soda were added. The dye separates out in deep red flakes, it is filtered off after completion of the combination, washed neutral and advantageously used in paste form. After drying, it forms a bluish burgundy powder and dissolves in concentrated sulfuric acid with a deep bluish red color.
In der folgenden Tabelle sind die Nuancen einiger weiterer Farbstoffe bzw. der daraus erhältlichen Farblacke angegeben:The following table shows the nuances of some other dyes or those from them available color lacquers:
des Farbstoffes
bzw.
der daraus erhältlichen
Lackenuance
of the dye
respectively.
the one obtainable from it
Lacquers
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE258654C true DE258654C (en) |
Family
ID=516459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT258654D Active DE258654C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE258654C (en) |
-
0
- DE DENDAT258654D patent/DE258654C/de active Active
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