DE79583C - - Google Patents
Info
- Publication number
- DE79583C DE79583C DENDAT79583D DE79583DA DE79583C DE 79583 C DE79583 C DE 79583C DE NDAT79583 D DENDAT79583 D DE NDAT79583D DE 79583D A DE79583D A DE 79583DA DE 79583 C DE79583 C DE 79583C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- naphthylamine
- yellow
- red
- dyes
- 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 9
- -1 sodium bisulfite compound Chemical class 0.000 claims description 8
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- 229940001607 sodium bisulfite Drugs 0.000 claims description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 5
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 4
- YXAOOTNFFAQIPZ-UHFFFAOYSA-N 1-nitrosonaphthalen-2-ol Chemical compound C1=CC=CC2=C(N=O)C(O)=CC=C21 YXAOOTNFFAQIPZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 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 1
- 238000010186 staining Methods 0.000 claims 1
- 210000002268 Wool Anatomy 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000019219 chocolate Nutrition 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- SYUYTOYKQOAVDW-UHFFFAOYSA-N 2-nitrosonaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(N=O)C=CC2=C1 SYUYTOYKQOAVDW-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- OMFHQUCUWSMFOJ-FMONCPFKSA-N COMP protocol Chemical compound ClCCN(CCCl)P1(=O)NCCCO1.O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1.C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1.C([C@H](C[C@]1(C(=O)OC)C=2C(=C3C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)=CC=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OMFHQUCUWSMFOJ-FMONCPFKSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002966 varnish Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
- Printing Methods (AREA)
Description
KAiSFRUC1HJSKAiSFR UC 1 HJ S
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
DAHL & COMP, in BARMEN.DAHL & COMP, in BARMEN.
Nitroso-ß- naphtols.Nitroso-ß-naphtols.
Patentirt im Deutschen Reiche vom 8. Mai 1894 ab.Patented in the German Empire on May 8, 1894.
Trägt man Nitroso-ß-Naphtol in eine auf ca. 50° erwärmte concentrate Lösung von Natriumbisulfit ein,.so löst sich das Nitrosonaphtol anfangs mit brauner Farbe auf. Nach kurzer Zeit wird die Masse plötzlich unter starker Selbsterwärmung dick, indem sich silbergraue Kryställchen ausscheiden, die das Natronsalz einer Bisulfitverbindung des Nitrosoß-Naphtols bilden. Diese Natriumbisulfitverbindung läfst sich im Gegensatz zum freien Njtrosonaphtol mit Diazoverbindungen in alkalischer Lösung zu Azofarbstoffen combiriiren, welche sowohl ungeheizte Wolle im sauren Bade als auch chromgebeizte Wolle in braunen Tönen anfärben.If you apply nitroso-ß-naphtol in one 50 ° heated concentrate solution of sodium bisulfite, .this is how the nitrosonaphthol dissolves initially with brown color. After a short time, the mass suddenly becomes thick with strong self-heating by itself silver-gray crystals secrete, which are the sodium salt of a bisulfite compound of nitrous naphthol form. In contrast to the free one, this sodium bisulfite compound can be dissolved Combine Njtrosonaphtol with diazo compounds in an alkaline solution to form azo dyes, which both unheated wool in an acid bath and chrome-stained wool in brown Coloring tones.
In nachstehender Tabelle sind die aus der Natriumbisulfitverbindung des Nitroso-ß-Naphtols und verschiedenen Diazoverbindungen zu erhaltenden Farbstoffe zusammengestellt:In the table below are those from the sodium bisulfite compound of nitroso-ß-naphthol and various diazo compounds to be obtained:
sauren Badedyes wool in
acid bath
monosulfosäureβj-naphthylamine-a ^
monosulfonic acid
Besonders werthvoll sind die mittelst der Diazoverbindungen des α- und ß-Naphtylamins hergestellten Farbstoffe.The diazo compounds of α- and β-naphthylamine are especially valuable manufactured dyes.
Die Herstellung der Farbstoffe geschieht nach den allgemein bekannten Methoden derart, dafs man 14,4 kg Naphtylamin mittelst Salzsäure und salpetrigsaurem Natron in die Diazoverbindnng überführt und letztere unter gutem Umrühren in eine mit Soda alkalisch gehaltene Lösung der Natriumbisulfitverbindung aus 17,3 kg (1 Mol.) Nitroso-ß-Naphtol einlaufen läfst. Der entstehende Farbstoff kann sofort mit Salz abgeschieden werden.The production of the dyes takes place according to the generally known methods in such a way that 14.4 kg of naphthylamine are added to the diazo compound using hydrochloric acid and nitrous acid transferred and the latter with thorough stirring in one kept alkaline with soda Run in solution of the sodium bisulfite compound from 17.3 kg (1 mol.) Of nitroso-ß-naphtol running. The resulting dye can be deposited immediately with salt.
Die Farbstoffe aus den beiden Naphtylaminen sind in Wasser leicht mit brauner Farbe löslich. Ungeheizte Wolle wird von dem Farbstoff aus β-Naphtylamin in gelberer Nuance angefärbt als von dem aus a-Naphtylamin. Die Färbungen sind sehr lichtecht.The dyes from the two naphthylamines are easily soluble in water with a brown color. Unheated wool is made from the dye from β-naphthylamine in a more yellow shade colored as from that from a-naphthylamine. The colorations are very lightfast.
Auf chromgebeizte Wolle erzielt man mit letzterem Farbstoff eine rothbraune, mit ersterem eine chokoladebraune Nuance. Die Chromfärbungen sind walkecht.On chrome-stained wool, the latter dye produces a red-brown color, the former a chocolate brown shade. The chrome colors are whackfast.
Claims (2)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE79583C true DE79583C (en) |
Family
ID=352211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT79583D Active DE79583C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE79583C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126548B (en) * | 1959-05-20 | 1962-03-29 | Basf Ag | Process for the production of azo dyes and their metal complex compounds |
-
0
- DE DENDAT79583D patent/DE79583C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126548B (en) * | 1959-05-20 | 1962-03-29 | Basf Ag | Process for the production of azo dyes and their metal complex compounds |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE79583C (en) | ||
| DE2363603A1 (en) | AZO DYES | |
| DE65651C (en) | Process for the preparation of primary disazo and tetrazo dyes from amidonaphthol disulfonic acid | |
| DE46623C (en) | Process for the preparation of azo dyes from ^ -naphtylamine-fJ-monosulfonic acid | |
| DE455953C (en) | Process for the preparation of monoazo dyes | |
| DE556479C (en) | Process for the preparation of water-insoluble azo dyes | |
| US1878243A (en) | Process for manufacturing azodyestuffs | |
| DE242051C (en) | ||
| DE58415C (en) | Process for the preparation of secondary disazo dyes for printing and dyeing from amidophthalic acid | |
| DE139213C (en) | ||
| DE695348C (en) | Process for the preparation of water-insoluble disazo dyes | |
| DE83572C (en) | ||
| DE614603C (en) | Process for the preparation of water-insoluble monoazo dyes | |
| DE423090C (en) | Process for the preparation of aminoazo compounds | |
| DE153299C (en) | ||
| DE118078C (en) | ||
| DE109063C (en) | ||
| DE155740C (en) | ||
| DE652215C (en) | Process for the production of water-soluble azo dyes | |
| DE281448C (en) | ||
| DE118392C (en) | ||
| DE92799C (en) | ||
| DE697000C (en) | Process for the preparation of o-oxyazo dyes | |
| DE110711C (en) | ||
| DE569305C (en) | Process for the preparation of azo dyes |