DE2735264A1 - YELLOW-BROWN DISPERSION DYES - Google Patents
YELLOW-BROWN DISPERSION DYESInfo
- Publication number
- DE2735264A1 DE2735264A1 DE19772735264 DE2735264A DE2735264A1 DE 2735264 A1 DE2735264 A1 DE 2735264A1 DE 19772735264 DE19772735264 DE 19772735264 DE 2735264 A DE2735264 A DE 2735264A DE 2735264 A1 DE2735264 A1 DE 2735264A1
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- formula
- parts
- dyes
- dispersion 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims description 15
- 239000006185 dispersion Substances 0.000 title 1
- 239000000835 fiber Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000000986 disperse dye Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
Classifications
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
- C09B29/0826—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene/-alkynylene-O)(-alkenylene/-alkynylene-CN)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
-2- O.Z. 32-2- O.Z. 32
Gelbbraune DispersionsfarbstoffeYellow-brown disperse dyes
Die Erfindung betrifft gelbbraune Dispersionsfarbstoffe der allgemeinen Formel IThe invention relates to yellow-brown disperse dyes in general Formula I.
■ Ν ^■ Ν ^
C2H4O-C-NHCH(CH3)2 C 2 H 4 OC-NHCH (CH 3 ) 2
in der die Beste X und T unabhängig voneinander Chlor oder Brom bedeuten. in which the best X and T are independently chlorine or bromine.
Zur Herstellung der Farbstoffe der Formel I kann man eine Diazoniumverbindung von Aminen der Formel IIA diazonium compound can be used to prepare the dyes of the formula I of amines of the formula II
mit einer Kupplungskomponente der Formel IIIwith a coupling component of the formula III
C2H4CN III C 2 H 4 CN III
"C2H4O-C-NH-CH(CH3)2 "C 2 H 4 OC-NH-CH (CH 3 ) 2
in an sich bekannter Weise umsetzen.implement in a manner known per se.
9098O8/OO6S9098O8 / OO6S
-2- O.Z. 32-2- O.Z. 32
CH CNCH CN
2 4 / 2 4 / C0H,0-C-HH-CHC 0 H, 0-C-HH-CH
Sie Farbstoffe der Formel I eignen sich zum Färben von synthetischen und halbsynthetischen Fasern, z. B.: Polyamiden, Folyacrylfasern und insbesondere Celluloseacetaten und Polyestern. Man erhält Färbungen mit hervorragenden Licht-, Haß- und Thermofixierechtheiten.The dyes of the formula I are suitable for dyeing synthetic ones and semi-synthetic fibers, e.g. For example: polyamides, polyacrylic fibers and especially cellulose acetates and polyesters. Colorations are obtained with excellent light, hate and thermosetting fastness.
Gegenüber chemisch naheliegenden Farbstoffen aus der japanischen Patentveröffentlichung 42-3009 (Beispiel 5 «nd Beispiel 22) zeichnen eich die Farbstoffe der Formel I durch besseres Aufziehvermögen auf Polyesterfasern (insbesondere in Gegenwart von Carriern) und vor allem auf Polyamid und Celluloseacetatfasern aus.Compared to chemically obvious dyes from Japanese Patent Publication 42-3009 (Example 5 and Example 22), they are distinguished Dyes of the formula I due to better absorption on polyester fibers (especially in the presence of carriers) and especially on polyamide and cellulose acetate fibers.
In den folgenden Beispielen beziehen sich die Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following examples, the data refer to parts and Unless otherwise stated, percentages based on weight.
90980β/00δ590980β / 00δ5
-4- ο.Ζ. 32 733-4- ο.Ζ. 32 733
83 Teile 2,6-Dichlor-4-nitroanilin werden in 36O Teilen 85 proz. Schwefelsäure gelöst, bei 0 bis 5 °C mit I30 Teilen 45 proz. Nitrosyl schwefel säure diazotiert und 3 bis 4 Stunden bei 3 bis 8 0C nachgerührt .83 parts of 2,6-dichloro-4-nitroaniline are 85 percent strength in 360 parts. Dissolved sulfuric acid, at 0 to 5 ° C with I30 parts 45 percent. Nitrosyl sulfuric acid diazotized and stirred at 3 to 8 0 C for 3 to 4 hours.
115 Teile N-(2-Cyanäthyl)-lI-(isopropylcarbamoyl-2-oxyäthyl)-anilin werden in 400 Teilen Eisessig heiß gelöst und in eine Mischung aus 800 Teilen Wasser, 1200 Teilen Eis und 4 Teilen Amidosulfonsäure gegeben. Anschließend läßt man bei -5 bis 0 0C die Diazoniumsalzlosung zulaufen und verdünnt auf incsesamt 6OOO Vol.-Teile. Nach beendeter Kupplung wird der Farbstoff abgesaugt, mit warmem Wässer neutral gewaschen und unter vermindertem Druck bei 60 C getrocknet. Man erhält 186 Teile des Farbstoffs der Formel:115 parts of N- (2-cyanoethyl) -lI- (isopropylcarbamoyl-2-oxyethyl) aniline are dissolved in 400 parts of hot glacial acetic acid and added to a mixture of 800 parts of water, 1200 parts of ice and 4 parts of sulfamic acid. Then allowed at -5 to 0 0 C, the diazonium salt solution and diluted to run incsesamt 6OOO parts by volume. After coupling has ended, the dye is filtered off with suction, washed neutral with warm water and dried at 60 ° C. under reduced pressure. 186 parts of the dye of the formula are obtained:
^C0H-O-C-NH-CH Cl 24J ^ C 0 HOC-NH-CH Cl 24 J
der auf Polyester- und Celluloseacetatfasern farbstarke gelbbraune Färbungen mit hervorragenden Licht-, Schweiß-, Verkoch- und Thermofixierechtheiten liefert.the yellow-brown one, which is strongly colored on polyester and cellulose acetate fibers Dyes with excellent light, perspiration, boiling and thermosetting fastness properties supplies.
-5--5-
909808/0065909808/0065
-5- ο. ζ. 32 733-5- ο. ζ. 32 733
Fein verteilte, in wäßrige Färbeflotten leicht einrührbare Farbstoffpräparate erhält man z. B. wie folgt:Finely divided dye preparations which can be easily stirred into aqueous dye liquors you get z. B. as follows:
Der Farbstoff (getrockneter Farbstoff oder feuchtes Preßgut) wird in Gegenwart von Dispergiermitteln bei Temperaturen von 40 - 100 C, vorzugsweise bei 60-90 C, gemahlen. Vorteilhaft ist auch eine Vorbehandlung, z. B. Erwärmen in wäßriger Suspension oder als wasserfeuchte Paste gegebenenfalls unter Zusatz von Dispergier- und/oder organischen Lösungsmitteln auf Temperaturen von 50 - 100 0C.The dyestuff (dried dyestuff or moist pressed material) is ground in the presence of dispersants at temperatures of 40-100.degree. C., preferably at 60-90.degree. Pre-treatment, e.g. B. heating in aqueous suspension or as a water-wet paste, optionally with addition of dispersants and / or organic solvents at temperatures of 50-100 0 C.
Die in der folgenden Tabelle aufgeführten Farbstoffe der Formel I wurden entsprechend hergestellt und haben vergleichbare coloristische Eigenschaften.The dyes of the formula I listed in the table below were prepared accordingly and have comparable coloristic properties Properties.
Bsp.-Kr. X YE.g. Kr. X Y
2 Cl Br2 Cl Br
3 Br Br3 Br Br
BASF Aktiengesellschaft A^-BASF Aktiengesellschaft A ^ -
/7/ 7
909808/0065909808/0065
Claims (2)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772735264 DE2735264A1 (en) | 1977-08-05 | 1977-08-05 | YELLOW-BROWN DISPERSION DYES |
| IT26345/78A IT1097990B (en) | 1977-08-05 | 1978-07-31 | YELLOW-BROWN DISPERSION DYES |
| FR7822812A FR2399462A1 (en) | 1977-08-05 | 1978-08-02 | BROWN-YELLOW DISPERSABLE COLORANTS AND THEIR PREPARATION |
| GB7832184A GB2002800B (en) | 1977-08-05 | 1978-08-03 | Yellowish-brown disperse dyes |
| JP9503578A JPS5429332A (en) | 1977-08-05 | 1978-08-05 | Yellowish brown disperse dyestuff |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772735264 DE2735264A1 (en) | 1977-08-05 | 1977-08-05 | YELLOW-BROWN DISPERSION DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2735264A1 true DE2735264A1 (en) | 1979-02-22 |
Family
ID=6015665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772735264 Withdrawn DE2735264A1 (en) | 1977-08-05 | 1977-08-05 | YELLOW-BROWN DISPERSION DYES |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5429332A (en) |
| DE (1) | DE2735264A1 (en) |
| FR (1) | FR2399462A1 (en) |
| GB (1) | GB2002800B (en) |
| IT (1) | IT1097990B (en) |
-
1977
- 1977-08-05 DE DE19772735264 patent/DE2735264A1/en not_active Withdrawn
-
1978
- 1978-07-31 IT IT26345/78A patent/IT1097990B/en active
- 1978-08-02 FR FR7822812A patent/FR2399462A1/en active Pending
- 1978-08-03 GB GB7832184A patent/GB2002800B/en not_active Expired
- 1978-08-05 JP JP9503578A patent/JPS5429332A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5429332A (en) | 1979-03-05 |
| GB2002800B (en) | 1982-02-10 |
| IT7826345A0 (en) | 1978-07-31 |
| IT1097990B (en) | 1985-08-31 |
| FR2399462A1 (en) | 1979-03-02 |
| GB2002800A (en) | 1979-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |