DE855390C - Process for dyeing leather - Google Patents
Process for dyeing leatherInfo
- Publication number
- DE855390C DE855390C DEG5546A DEG0005546A DE855390C DE 855390 C DE855390 C DE 855390C DE G5546 A DEG5546 A DE G5546A DE G0005546 A DEG0005546 A DE G0005546A DE 855390 C DE855390 C DE 855390C
- Authority
- DE
- Germany
- Prior art keywords
- same
- acid
- diamino
- aminonaphthalene
- brown
- 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
Links
- 239000010985 leather Substances 0.000 title claims description 13
- 238000004043 dyeing Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 29
- 239000000975 dye Substances 0.000 claims description 20
- MCTQNEBFZMBRSQ-UHFFFAOYSA-N (3-amino-4-phenyldiazenylphenyl)azanium;chloride Chemical class Cl.NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 MCTQNEBFZMBRSQ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001555 benzenes Chemical class 0.000 claims description 6
- 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 6
- -1 4,4'-diaminodiphenyl compound Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 125000006267 biphenyl group Chemical group 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 5
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- GVEDOIATHPCYGS-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)benzene Chemical group CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 GVEDOIATHPCYGS-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- YYRVBCBZQPTVEO-UHFFFAOYSA-N 2-amino-5-methylbenzene-1,4-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O YYRVBCBZQPTVEO-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NVLVJHQJUHUFAC-UHFFFAOYSA-N 3-aminobenzene-1,2-disulfonic acid Chemical class NC1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O NVLVJHQJUHUFAC-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- KKBQCLVIBFUKGQ-UHFFFAOYSA-N 4-amino-5-methylbenzene-1,3-disulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1N KKBQCLVIBFUKGQ-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- 206010037867 Rash macular Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/42—Trisazo dyes ot the type the component K being a diamine or polyamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zum Färben von Leder Die Verwendung von braunen Baumwollfarbstoffen zum Färben von Leder ist altbekannt, besonders auch die Verwendung von Trisazofarbstoffen aus tetrazotierten 4, 4'-Diaminodiphenylverbindungen, kupplungsfähigen o-Oxycarbonsäuren der Benzolreihe und Monoazofarbstoffen der Chrysoidinreihe, d. h. Kupplungsprodukten aus diazotierten Aminen der Benzol-und Naphthalinreihe mit m-Phenylendiamin.Method of dyeing leather The use of brown cotton dyes for dyeing leather is well known, especially the use of trisazo dyes from tetrazotized 4,4'-diaminodiphenyl compounds, o-oxycarboxylic acids capable of coupling the benzene series and monoazo dyes of the chrysoidin series, d. H. Coupling products from diazotized amines of the benzene and naphthalene series with m-phenylenediamine.
In solchen braunen Trisazofarbstoffen wurden bisher, soweit uns bekannt, nur solche sulfierte Monoazofarbstoffe der Chrysoidinreihe verwendet, die nicht mehr als eine Sulfonsäuregruppe enthalten. Diese bekannten Baumwollfarbstoffe werden aus neutralem Färbebad auf Leder gefärbt und geben oberflächliche Färbungen von großer Deckkraft, ohne das Leder einzufärben. In Kombination mit durchfärbenden sauren Farbstoffen, die aus saurer Flotte gefärbt werden müssen, weisen diese Baumwollfarbstoffe als großen Nachteil eine viel zu geringe Löslichkeit in der gebräuchlichen ameisensauren Färbeflotte auf, so daß Fällungen auftreten und ungleichmäßige, fleckige Färbungen entstehen.So far, as far as we know, such brown trisazo dyes only those sulfated monoazo dyes of the chrysoidin series are used that are not contain more than one sulfonic acid group. These are known cotton dyes Dyed from a neutral dye bath on leather and give superficial colorations of great coverage without coloring the leather. In combination with through-coloring These cotton dyes have acidic dyes that have to be dyed from acidic liquor the major disadvantage is that the solubility in common formic acid is far too low Dye liquor up, so that precipitations occur and uneven, blotchy dyeings develop.
Es wurde nun die wertvolle Beobachtung gemacht, daß Trisazofarbstoffe aus tetrazotierten 4, 4'-Diaminodiphenylverbindungen, kupplungsfähigen o-Oxycarbonsäuren der Benzolreihe und sulfierten Chrysoidinfarbstoffen aus diazotierten primären Aminen der Benzol- und Naphthalinreihe, die mindestens zwei Sulfonsäuregruppen enthalten sollen und im übrigen noch weitere in Azofarbstoffen übliche Substituenten enthalten können, und m-Phenylendiamin oder m-Toluylendiamin zum Färben von Leder hervorragend geeignet sind, weil sie in saurem Medium gut wasserlöslich sind und gutes Ziehvermögen auf Leder besitzen. Sie ergeben sehr gleichmäßige, reine Lederfärbungen, die sich durch gute Echtheit im Fettliquor auszeichnen.The valuable observation has now been made that trisazo dyes from tetrazotized 4,4'-diaminodiphenyl compounds, o-oxycarboxylic acids capable of coupling the benzene series and sulfated chrysoidin dyes from diazotized primary amines the benzene and naphthalene series, which contain at least two sulfonic acid groups should and also contain other substituents customary in azo dyes can, and m-phenylenediamine or m-tolylenediamine are excellent for dyeing leather are suitable because they are readily water-soluble in an acidic medium and have good drawability own on leather. They result in very even, pure leather colorations that characterized by good authenticity in fatty liquor.
Man erhält die erfindungsgemäß verwendbaren Farbstoffe dadurch, daß man i Mol einer tetrazotierten 4, 4'-Diaminodiphenylverbindung mit i Mol einer kupplungsfähigen o-Oxycarbonsäure der Benzolreihe und i Mol eines sulfierten Monoazofarbstoffes der Chrysoidinreihe von der Formel kuppelt, in welcher R Wasserstoff oder die Methylgruppe und A den Rest einer Aminobenzol- oder Aminonaphthalinpolysulfonsäure bedeuten.The dyes which can be used according to the invention are obtained by adding 1 mole of a tetrazotized 4,4'-diaminodiphenyl compound with 1 mole of a couplable o-oxycarboxylic acid of the benzene series and 1 mole of a sulfated monoazo dye of the chrysoidin series of the formula couples, in which R is hydrogen or the methyl group and A is the radical of an aminobenzene or aminonaphthalene polysulfonic acid.
Die Kupplung erfolgt in neutralem bis alkalischem Medium. Brauchbare 4, 4'-Diaminodiphenylverbindungen sind vor allem das Benzidin, dann das 3, 3'-oder 2, 2'-Dimethyl- oder -Dichlor-4, 4'-diaminodiphenyl, das 3, 3'-Dimethoxy-4, 4'-diaminodiphenyl. Kupplungsfähige o-Oxycarbonsäuren der Benzolreihe sind vor allem die Salicylsäure, ferner die o-Kresotinsäure, die m-Kresotinsäure usw. Zur Herstellung der verwendeten sulfierten Chrysoidinfarbstoffe eignen sich unter anderen die Diazoverbindungen folgender Aminobenzol- bzw. Aminonaphthalinpolysulfonsäuren a) Aminobenzoldisulfonsäuren, wie i-Aminobenzol-2, 5-disulfonsäure, i-Aminobenzol-2, 4-disulfonsäure, i-Aminobenzol-3, 5-disulfonsäure, 2-Amino-i-methylbenzol-3, 5-disulfonsäure, 4-Amino-i-methylbenzol-2, 5-disulfonsäure usw. ; b) Aminonaphthalindi- und trisulfonsäuren, wie 2-Aminonaphthalin-4, 8-disulfonsäure 2-Aminonaphthalin-6, 8- oder 5, 7-disulfonsäure, i-Aminonaphthalin-3, 6, 8-trisulfonsäure usw.The coupling takes place in a neutral to alkaline medium. Useful 4, 4'-Diaminodiphenylverbindungen are mainly the benzidine, then the 3, 3'- or 2, 2'-dimethyl- or -dichloro-4, 4'-diaminodiphenyl, the 3, 3'-dimethoxy-4, 4'-diaminodiphenyl. Couplable o-oxycarboxylic acids of the benzene series are mainly salicylic acid, also o-cresotinic acid, m-cresotinic acid, etc. For the production of the used Sulphated chrysoidin dyes are suitable, among others, the diazo compounds the following aminobenzene or aminonaphthalene polysulphonic acids a) aminobenzene disulphonic acids, such as i-aminobenzene-2, 5-disulphonic acid, i-aminobenzene-2, 4-disulphonic acid, i-aminobenzene-3, 5-disulfonic acid, 2-amino-i-methylbenzene-3, 5-disulfonic acid, 4-amino-i-methylbenzene-2, 5-disulfonic acid, etc.; b) aminonaphthalenedi- and trisulfonic acids, such as 2-aminonaphthalene-4, 8-disulfonic acid, 2-aminonaphthalene-6, 8- or 5, 7-disulfonic acid, i-aminonaphthalene-3, 6, 8-trisulfonic acid, etc.
Das folgende Beispiel veranschaulicht die Erfindung, ohne sie zu beschränken. Die Teile sind Gewichtsteile und die Temperaturen sind Centigrad. Beispiel o,5 Teile des Trisazofarbstoffes der Formel werden in Zoo Teilen kochendem Wasser gelöst und im WalkfaB auf 4oo Teile von 65° gestellt. Man gibt ioo Teile chromgares Leder zu und färbt während 2o Minuten aus neutralem Bade. Dann werden 0,2 Teile Ameisensäure 85°o zugesetzt und während weiterer 20 Minuten sauer gefärbt. Nach dem Färben wird in üblicher Weise gelickert und weiter aufgearbeitet. Das Leder ist in egalen lebhaften braunen Tönen gefärbt.The following example illustrates the invention without limiting it. The parts are parts by weight and the temperatures are centigrade. Example o, 5 parts of the trisazo dye of the formula are dissolved in zoo parts of boiling water and placed in the WalkfaB to 400 parts of 65 °. 100 parts of chrome-baked leather are added and dyed for 20 minutes from a neutral bath. Then 0.2 part of formic acid 85 ° o is added and colored acidic for a further 20 minutes. After dyeing, it is leached and worked up in the usual way. The leather is colored in lively brown tones.
In der nachfolgenden Tabelle wird zur weiteren Veranschaulichung der
vorliegenden Erfindung eine Anzahl von Beispielen angeführt, wobei das Färbeverfahren
mit dem in diesem Beispiel beschriebenen übereinstimmt.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH855390X | 1947-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE855390C true DE855390C (en) | 1952-11-13 |
Family
ID=4542639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG5546A Expired DE855390C (en) | 1947-05-29 | 1951-03-30 | Process for dyeing leather |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE855390C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE950227C (en) * | 1953-01-30 | 1956-10-04 | Geigy Ag J R | Process for the production of brown leather dyes |
| DE1013019B (en) * | 1953-11-24 | 1957-08-01 | Cassella Farbwerke Mainkur Ag | Process for the preparation of brown tris and polyazo dyes |
| DE1018173B (en) * | 1954-03-11 | 1957-10-24 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1019026B (en) * | 1954-03-10 | 1957-11-07 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1021106B (en) * | 1954-03-11 | 1957-12-19 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1021969B (en) * | 1954-03-11 | 1958-01-02 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1056759B (en) * | 1955-10-17 | 1959-05-06 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
-
1951
- 1951-03-30 DE DEG5546A patent/DE855390C/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE950227C (en) * | 1953-01-30 | 1956-10-04 | Geigy Ag J R | Process for the production of brown leather dyes |
| DE1013019B (en) * | 1953-11-24 | 1957-08-01 | Cassella Farbwerke Mainkur Ag | Process for the preparation of brown tris and polyazo dyes |
| DE1015962B (en) * | 1953-11-24 | 1957-09-19 | Cassella Farbwerke Mainkur Ag | Process for the preparation of brown tris and polyazo dyes |
| DE1019027B (en) * | 1953-11-24 | 1957-11-07 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1019026B (en) * | 1954-03-10 | 1957-11-07 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1018173B (en) * | 1954-03-11 | 1957-10-24 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1021106B (en) * | 1954-03-11 | 1957-12-19 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1021969B (en) * | 1954-03-11 | 1958-01-02 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
| DE1056759B (en) * | 1955-10-17 | 1959-05-06 | Cassella Farbwerke Mainkur Ag | Process for the preparation of tris and polyazo dyes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE855390C (en) | Process for dyeing leather | |
| DE670935C (en) | Process for the production of complex copper compounds from polyazo dyes | |
| DE1619349A1 (en) | Dye mixture for browning fur | |
| DE639669C (en) | Process for dyeing leather | |
| DE900600C (en) | Process for the production of copper-containing dis- or polyazo dyes | |
| DE1084403B (en) | Process for the production of water-insoluble azo dyes | |
| DE965346C (en) | Process for the preparation of a water-insoluble monoazo dye | |
| DE427246C (en) | Process for the production of azo dyes | |
| DE572516C (en) | Process for dyeing vegetable fibers | |
| DE595187C (en) | Process for dyeing leather | |
| DE254277C (en) | ||
| DE268188C (en) | ||
| US2050811A (en) | Primary disazo compounds | |
| DE61950C (en) | Process for the preparation of trisazo dyes. (2 | |
| DE99468C (en) | ||
| DE60373C (en) | Process for the preparation of stain-coloring azo dyes | |
| DE815513C (en) | Process for the preparation of disazo or polyazo dyes | |
| CH257380A (en) | Process for dyeing leather. | |
| DE572473C (en) | Process for the production of water-insoluble azo dyes on the fiber | |
| DE880622C (en) | Process for the preparation of copper-containing disazo dyes | |
| DE480298C (en) | Process for coloring acetyl cellulose with poorly soluble or insoluble dyes or colored organic compounds | |
| DE567773C (en) | Process for the production of azo dyes | |
| DE569305C (en) | Process for the preparation of azo dyes | |
| DE693586C (en) | Process for the production of colors on animal fibers or cellulose fibers or on mixtures of both types of fiber | |
| DE654459C (en) | Process for the production of condensation products |