DE60500C - Process for the preparation of real azo dyes for dyeing and printing from amidocarboxylic acids. (2 - Google Patents
Process for the preparation of real azo dyes for dyeing and printing from amidocarboxylic acids. (2Info
- Publication number
- DE60500C DE60500C DENDAT60500D DE60500DA DE60500C DE 60500 C DE60500 C DE 60500C DE NDAT60500 D DENDAT60500 D DE NDAT60500D DE 60500D A DE60500D A DE 60500DA DE 60500 C DE60500 C DE 60500C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- printing
- real
- azo dyes
- dyeing
- 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
- 239000002253 acid Substances 0.000 title claims description 27
- 239000000987 azo dye Substances 0.000 title claims description 3
- 238000004043 dyeing Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims 2
- 150000007513 acids Chemical class 0.000 title description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 238000005121 nitriding Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 6
- FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- VIDTTXQYJGYACL-UHFFFAOYSA-N 2,3-disulfobenzoic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1S(O)(=O)=O VIDTTXQYJGYACL-UHFFFAOYSA-N 0.000 description 1
- MFCDHQNPTNBIGC-UHFFFAOYSA-N 6-diazocyclohexa-2,4-diene-1-carboxylic acid Chemical class OC(=O)C1C=CC=CC1=[N+]=[N-] MFCDHQNPTNBIGC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- -1 Diazooxybenzoic acids Chemical class 0.000 description 1
- JKEBCAYUPGQDMC-UHFFFAOYSA-N [N+](=[N-])=C1C(C(C(=O)O)=CC=C1)C(=O)O Chemical class [N+](=[N-])=C1C(C(C(=O)O)=CC=C1)C(=O)O JKEBCAYUPGQDMC-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002966 varnish Substances 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
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
- C09B29/14—Hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt im Deutschen Reiche vom 15. März 1891 ab. Längste Dauer: 9. November 1904.Patented in the German Empire on March 15, 1891. Longest duration: November 9, 1904.
Nach den Angaben der Patentschrift No. 58271 entstehen durch Einwirkung von Diazobenzoesäuren bezw. Diazooxybenzoesäuren, deren Homologen oder von Diazophtalsäuren auf gewisse Phenole, Naphtole und deren Carbonsäuren werthvolle Farbstoffe, welche infolge der in ihnen enthaltenen Carboxylgruppen mit Chrom vorgebeizte Wolle waschecht anfärben, sowie für Druckereizwecke vorzüglich geeignet sind. Aufser den in der genannten Patentschrift aufgeführten Componenten liefert ferner die Dioxybenzoesäure (1-3-5), welche durch Verschmelzen der Disulfobenzoesäure mit Alkalien entsteht (Ann. 159, S. 222) und die bisher zur Darstellung von Azofarbstoffen keine Verwendung gefunden hat, vorzügliche Resultate.According to the information in patent specification no. 58271 arise due to the action of diazobenzoic acids respectively. Diazooxybenzoic acids, their Homologues or of diazophthalic acids on certain phenols, naphthols and their carboxylic acids valuable dyes, which because of the carboxyl groups they contain Dyeing chrome pre-stained wool so that it is washable, and is ideally suited for printing purposes are. In addition to the components listed in the cited patent, it also delivers the dioxybenzoic acid (1-3-5), which by Fusion of the disulfobenzoic acid with alkalis results (Ann. 159, p. 222) and the has so far found no use for the representation of azo dyes, excellent Results.
Farbstoff aus m-Amidobenzoesäure + Dioxybenzoesäure (1-3-5)·Dye from m-amidobenzoic acid + dioxybenzoic acid (1-3-5)
ι 3,7 kg m-Amidobenzoesäure werden in üblicher Weise mit einer Lösung von 7 kg Natriumnitrit diazotirt und alsdann allmälig in eine mit überschüssiger Soda versetzte Lösung von 1 5,4 kg Dioxybenzoesäure (1 -3-5) eingetragen. Die Farbstoffbildung ist in kurzer Zeit beendet, · worauf durch Ansäuern der Farbstoff in rothbraunen Flocken ausgeschieden wird.ι 3.7 kg of m-amidobenzoic acid are in the usual way with a solution of 7 kg of sodium nitrite diazotized and then gradually transferred to a solution of 1 5.4 kg mixed with excess soda Dioxybenzoic acid (1 -3-5) entered. the Dye formation is complete in a short time, whereupon the dye turns red-brown by acidification Flakes is excreted.
Der Farbstoff färbt mit Chrom vorgebeizte Wolle in goldgelben Tönen an. Ersetzt man im vorstehenden Beispiel die m-Amidobenzoesäure durch ihre Isomeren, durch Amidosalicylsäure bezw. deren Homologen , durch die Sulfosäuren dieser Amidocarbonsäuren oder durch Amidophtalsäure, so erhält man folgende Resultate:The dye stains pre-stained with chrome Wool in golden yellow tones. Replacing the m-amidobenzoic acid in the above example by their isomers, respectively by amidosalicylic acid. their homologues, through the sulfonic acids of these amidocarboxylic acids or by amidophthalic acid, the following results are obtained:
Farbstoff aus m-AmidobenzoesäureM-amidobenzoic acid dye
o-Amidobenzoesäureo-amidobenzoic acid
p-Amidobenzoesäure +p-amidobenzoic acid +
o-Amidosalicylsäure -f-o-amidosalicylic acid -f-
p-Amidosalicylsäure ~\- p-amidosalicylic acid ~ \ -
o-Amido-m-cresolcarbonsäure -f-o-amido-m-cresolcarboxylic acid -f-
- Amidosulfosalicylsäure ' -f-- amidosulfosalicylic acid '-f-
' - - Amidophtalsäure +'- - amidophthalic acid +
-)- Dioxybenzoesäure (1-3-) - Dioxybenzoic acid (1-3
5) goldgelb,
braunroth.
goldgelb,
braunroth.
braunroth.
braunroth.
braunroth.
goldgelb.5) golden yellow,
brownish red.
golden yellow,
brownish red.
brownish red.
brownish red.
brownish red.
golden yellow.
Dieselben Töne werden mit Hülfe der Chrombeize beim Drucken erzielt.The same tones can be achieved with the help of the chrome stain when printing.
Claims (1)
0-Amido-m-cresolcarbonsäure (C O OH: = 1: 2: 4),
0-amido-m-cresolcarboxylic acid (C O OH:
Amidosulfosalicylsäure (aus sulfirter Salicylsäure durch Nitriren und Reduciren) und Amidophtalsäure, OH: CH 3 : NH = ri ! 2: 4: 6),
Amidosulfosalicylic acid (from sulfated salicylic acid by nitriding and reducing) and amidophthalic acid,
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE60500C true DE60500C (en) |
Family
ID=334630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT60500D Expired - Lifetime DE60500C (en) | Process for the preparation of real azo dyes for dyeing and printing from amidocarboxylic acids. (2 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE60500C (en) |
-
0
- DE DENDAT60500D patent/DE60500C/en not_active Expired - Lifetime
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