DE1087302B - Process for the preparation of water-insoluble monoazo dyes - Google Patents
Process for the preparation of water-insoluble monoazo dyesInfo
- Publication number
- DE1087302B DE1087302B DEF25692A DEF0025692A DE1087302B DE 1087302 B DE1087302 B DE 1087302B DE F25692 A DEF25692 A DE F25692A DE F0025692 A DEF0025692 A DE F0025692A DE 1087302 B DE1087302 B DE 1087302B
- Authority
- DE
- Germany
- Prior art keywords
- water
- preparation
- monoazo dyes
- insoluble monoazo
- parts
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title 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 title claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- -1 amino compound Chemical class 0.000 claims description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- MQQDDBLVGSHZSW-UHFFFAOYSA-N acetamide;toluene Chemical compound CC(N)=O.CC1=CC=CC=C1 MQQDDBLVGSHZSW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- BFLLUSJLDZVACV-UHFFFAOYSA-N n-(3-aminophenyl)sulfonylacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=CC(N)=C1 BFLLUSJLDZVACV-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- LCXPSINUMRGEOE-UHFFFAOYSA-N C(C)(=O)NS(=O)(=O)C=1C=CC(=C(C=1)N)Cl Chemical compound C(C)(=O)NS(=O)(=O)C=1C=CC(=C(C=1)N)Cl LCXPSINUMRGEOE-UHFFFAOYSA-N 0.000 description 1
- GWRBRKFJOOUBPB-UHFFFAOYSA-N CC(N)=O.NC1=CC=CC=C1 Chemical compound CC(N)=O.NC1=CC=CC=C1 GWRBRKFJOOUBPB-UHFFFAOYSA-N 0.000 description 1
- DZYXSRVGZKRBSY-UHFFFAOYSA-N N-(3-amino-4-methoxyphenyl)sulfonylacetamide Chemical compound C(C)(=O)NS(=O)(=O)C=1C=CC(=C(C1)N)OC DZYXSRVGZKRBSY-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 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
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von wasserunlöslichen Monoazofarbstoffen Es wurde gefunden, daß man wertvolle wasserunlösliche Monoazofarbstoffe erhält, wenn man eine Aminoverbindung der allgemeinen Formel worin X Wasserstoff, Halogen, eine Alkyl- oder Alkoxygruppe, R, Wasserstoff oder eine Alkylgruppe und R2 einen niedrigmolekularen aliphatischen Säurerest, vorzugsweise einen Acetylrest bedeutet, dianotiert und mit von wasserlöslichmachenden Gruppen freien Azokomponenten der 2,3-Oxynaphthoesäurearylamid- oder Acylessigsäurearylamidreihe umsetzt.Process for the preparation of water-insoluble monoazo dyes It has been found that valuable water-insoluble monoazo dyes are obtained if an amino compound of the general formula is used where X is hydrogen, halogen, an alkyl or alkoxy group, R, hydrogen or an alkyl group and R2 is a low molecular weight aliphatic acid radical, preferably an acetyl radical, dianotized and reacted with azo components of the 2,3-oxynaphthoic arylamide or acylacetic arylamide series which are free from water-solubilizing groups.
Verfahrensgemäß zu verwendende Diazokomponenten sind beispielsweise 1-Aminobenzol-3-sulfonsäureacetylamid, 1-Aminobenzol-2-chlor-5-sulfonsäure-N-methyl-N-acetylamid, 1-Aminobenzol-2-methyl-5-sulfonsäureacetylamid, 1-Aminobenzol-2-methoxy-5-sulfonsäureacetylamid.Diazo components to be used according to the method are, for example 1-aminobenzene-3-sulfonic acid acetylamide, 1-aminobenzene-2-chloro-5-sulfonic acid-N-methyl-N-acetylamide, 1-aminobenzene-2-methyl-5-sulfonic acid acetylamide, 1-aminobenzene-2-methoxy-5-sulfonic acid acetylamide.
Als Azokomponenten werden die für die Herstellung von Azopigmentfarbstoffen gebräuchlichen Arylamide der 2-Oxynaphthalin-3-carbonsäure und der Acetessigsäure verwendet.The azo components are used for the production of azo pigment dyes common arylamides of 2-oxynaphthalene-3-carboxylic acid and acetoacetic acid used.
Die Kupplung der Ausgangskomponenten erfolgt nach üblichen Verfahren in vorzugsweise saurem wäßrigem Medium.The starting components are coupled using customary methods in preferably acidic aqueous medium.
Die so erhältlichen Pigmentfarbstoffe eignen sich besonders zum Färben von Lacken und Kunststoffen, zum Bedrucken und Färben von Textilien und Papier nach den üblichen Pigmentdruck- und Färbeverfahren und zur Faserspinnfärbung. Sie zeichnen sich durch sehr gute Lichtechtheit aus und sind gut lösungsmittel-und überspritzecht.The pigment dyes obtainable in this way are particularly suitable for dyeing of paints and plastics, for printing and dyeing textiles and paper the usual pigment printing and dyeing processes and for fiber spin dyeing. they draw are characterized by very good lightfastness and are well solvent-sprayed and sprayed over.
Gegenüber dem aus der deutschen Patentschrift 821977, Beispiel 4, bekannten wasserunlöslichen Monoazofarbstoff zeichnet sich der erfindungsgemäß aus dianotiertem 1-Aminobenzol-3-sulfonsäureacetylamid und Acetoacetylaminobenzol erhältliche Farbstoff durch wesentlich verbesserte Lösungsmittelechtheit aus.Compared to that from the German patent specification 821977, Example 4, known water-insoluble monoazo dye is distinguished according to the invention dianotated 1-aminobenzene-3-sulfonic acid acetylamide and acetoacetylaminobenzene are available Dye is characterized by significantly improved solvent fastness.
In den folgenden Beispielen stehen Volumteile zu Gewichtsteilen im Verhältnis von Millilitern zu Gramm.In the following examples, parts by volume are related to parts by weight Ratio of milliliters to grams.
Beispiel 1 24,4 Gewichtsteile 1-Amino-2-methoxybenzol-5-sulfonsäureacetylamid werden in üblicher Weise dianotiert. Zu der geklärten Diazotierungslösung werden 25 Volumteile Eisessig und anschließend die wäßrige Lösüng des Natriumsalzes von 36 Gewichtsteilen 1-(2',3' - Hydroxynaphthoylamino) -5-chlor-2,4-dimethoxybenzol gegeben. Nach Beendigung der Kupplung wird der entstandene Farbstoff abgesaugt, gewaschen und getrocknet.Example 1 24.4 parts by weight of 1-amino-2-methoxybenzene-5-sulfonic acid acetylamide are dianotated in the usual way. Become the clarified diazotization solution 25 parts by volume of glacial acetic acid and then the aqueous solution of the sodium salt of 36 parts by weight of 1- (2 ', 3' -hydroxynaphthoylamino) -5-chloro-2,4-dimethoxybenzene given. After the coupling has ended, the resulting dye is suctioned off, washed and dried.
3 Gewichtsteile des so erhaltenen Pigmentfarbstoffes werden in 100 Gewichtsteilen eines Nitroalkyd-Harzlackes (mit einem Festkörpergehalt von etwa 22%) in einer Trichtermühle angerieben. Mit dem auf Spritzviskosität eingestellten Lack lassen sich bordofarbene Lackierungen mit sehr guter Überspritzechtheit und hoher Lichtechtheit erzielen.3 parts by weight of the pigment dye thus obtained are in 100 Parts by weight of a nitroalkyd resin varnish (with a solids content of approx 22%) ground in a funnel mill. With the set to spray viscosity Lacquer can be bordo-colored lacquers with very good overspray fastness and achieve high lightfastness.
Beispiel 2 24,8 Gewichtsteile 1-Amino-2-chlorbenzol-5-sulfonsäureacetylamid werden wie üblich dianotiert und, ähnlich wie im Beispiel 1, mit 27 Gewichtsteilen 1-(2',3'-Hydroxynaphthoylamino)-benzol gekuppelt.Example 2 24.8 parts by weight of 1-amino-2-chlorobenzene-5-sulfonic acid acetylamide are dianotized as usual and, similar to Example 1, with 27 parts by weight 1- (2 ', 3'-hydroxynaphthoylamino) benzene coupled.
Dispergiert man 20 Gewichtsteile des isolierten Farbstoffes mit 75 Volumteilen Wasser und 5 Gewichtsteilen eines Dispergiermittels, so lassen sich mit dieser Dispersion nach Einarbeiten in übliche Druckpasten orangefarbene Textildrucke von sehr guten Naß- und Lichtechtheiten erzielen.20 parts by weight of the isolated dye are dispersed with 75 Parts by volume of water and 5 parts by weight of a dispersant can be with this dispersion, after incorporation into customary printing pastes, orange-colored textile prints achieve very good wet and light fastness properties.
In ähnlicher Weise werden mit den in der folgenden Tabelle angeführten
Diazo- und Azokomponenten Pigmentfarbstoffe erhalten die Lacke, Papier und Textilien
in den angegebenen Farbtönen licht- und naßechtfärben:
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25692A DE1087302B (en) | 1958-05-06 | 1958-05-06 | Process for the preparation of water-insoluble monoazo dyes |
| BE578193A BE578193A (en) | 1958-05-06 | 1959-04-28 | Water-insoluble monoazo dyes, and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25692A DE1087302B (en) | 1958-05-06 | 1958-05-06 | Process for the preparation of water-insoluble monoazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1087302B true DE1087302B (en) | 1960-08-18 |
Family
ID=7091725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF25692A Pending DE1087302B (en) | 1958-05-06 | 1958-05-06 | Process for the preparation of water-insoluble monoazo dyes |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE578193A (en) |
| DE (1) | DE1087302B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2367856A1 (en) * | 1976-09-08 | 1978-05-12 | Acna | Azo, anthraquinone, nitro:amino and azamethine dyes for polyamide(s) - contg. sulphonamido carbonyl gps. and giving fast, level dyeings |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE821977C (en) * | 1949-10-02 | 1951-11-22 | Basf Ag | Process for the production of azo dyes |
-
1958
- 1958-05-06 DE DEF25692A patent/DE1087302B/en active Pending
-
1959
- 1959-04-28 BE BE578193A patent/BE578193A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE821977C (en) * | 1949-10-02 | 1951-11-22 | Basf Ag | Process for the production of azo dyes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2367856A1 (en) * | 1976-09-08 | 1978-05-12 | Acna | Azo, anthraquinone, nitro:amino and azamethine dyes for polyamide(s) - contg. sulphonamido carbonyl gps. and giving fast, level dyeings |
Also Published As
| Publication number | Publication date |
|---|---|
| BE578193A (en) | 1959-08-17 |
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