DE2051318A1 - Phenyl fluorene dyestuffs - for acid-modified textiles esp polyesters and acrylonitrile polymers giving fast blue shades - Google Patents
Phenyl fluorene dyestuffs - for acid-modified textiles esp polyesters and acrylonitrile polymers giving fast blue shadesInfo
- Publication number
- DE2051318A1 DE2051318A1 DE2051318A DE2051318A DE2051318A1 DE 2051318 A1 DE2051318 A1 DE 2051318A1 DE 2051318 A DE2051318 A DE 2051318A DE 2051318 A DE2051318 A DE 2051318A DE 2051318 A1 DE2051318 A1 DE 2051318A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- polyesters
- esp
- parts
- acrylonitrile polymers
- 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
Classifications
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- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/70—Material containing nitrile groups
- D06P3/76—Material containing nitrile groups using basic dyes
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- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/522—Polyesters using basic dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Description
Verfahren zum Färben von sauer modifiziertem extilmaterial aus Polyestern und Acrylnitrilpolymerisaten Die Erfindung betrifft ein Verfahren zum Färben von sauer modifiziertem Textilmaterial mit Farbstoffen der allgemeinen Formel in der X e ein An R1 und R2 Wasserstoff oder Alkylreste mit 1 bis 4 Kohlenstoffatomen bedeuten und wobei die Benzolringe noch durch Chlor oder Methyl substituiert sein können. Die Herstellung solcher Farbstoffe ist aus der US-Patentschrift 3 344 189 bekannt.Process for dyeing acid-modified textile material made from polyesters and acrylonitrile polymers The invention relates to a process for dyeing acid-modified textile material with dyes of the general formula in which X e is R1 and R2 are hydrogen or alkyl radicals having 1 to 4 carbon atoms and the benzene rings can also be substituted by chlorine or methyl. The preparation of such dyes is known from US Pat. No. 3,344,189.
Im einzelnen kommen als Reste R1 und R2 neben vorzugsweise Wasserstoff, Propyl oder Butyl und insbesondere Methyl oder Äthyl in Betracht.In particular, as radicals R1 and R2, in addition to preferably hydrogen, Propyl or butyl and in particular methyl or ethyl can be considered.
Anionen X e sind z.B. Chlorid, Bromid, Nitrat, Sulfat, Methosulfat, Äthosulfat, Formiat, Acetat, Tetrachlorozinkat oder Tetrafluoroborat.Anions X e are e.g. chloride, bromide, nitrate, sulfate, methosulfate, Ethosulfate, formate, acetate, tetrachlorozincate or tetrafluoroborate.
Die Farbstoffe ergeben nach den für das Färben von Acrylnitrilpolymerisaten und sauer modifizierten Polyestern gebräuchlichen Färbserfahren marineblaue bis grünblaue Färbungen mit guten Echtheiten, insbesondere guter Licht- und Dekaturechtheit.The dyes are based on those used for dyeing acrylonitrile polymers and acid-modified polyesters common dyeing processes from navy blue to green-blue dyeings with good fastness properties, in particular good light and decoration fastness.
Angaben über Teile und Prozente in den folgenden Beispielen beziehen sich auf das Gewicht.Parts and percentages in the following examples relate to focus on the weight.
Beispiel 1 In ein ungefähr 80 0C warmes Färbe bad aus 4000 Teilen Wasser, 20 Teilen Natriumsulfat, 3 Teilen 3obiger Essigsäure und 0,5 Teilen des Farbstoffes der Formel bringt man 100 Teile Polyacrylnitrilfaser ein, steigert innerhalb von 30 Minuten die Temperatur auf 1000C und färbt 45 Minuten bei Kochtemperatur. Nach dieser Zeit ist das Färbebad fast völlig erschöpft. Das gefärbte Gut wird wie üblich gespült und getrocknet. Die in grünstichig blauem Ton gefärbte Faser ist sehr gut licht-, wasch- und dekaturecht.EXAMPLE 1 In a dye bath at about 80 ° C. made of 4000 parts of water, 20 parts of sodium sulfate, 3 parts of acetic acid and 0.5 part of the dye of the formula 100 parts of polyacrylonitrile fibers are introduced, the temperature is increased to 100 ° C. over the course of 30 minutes and dyeing is carried out for 45 minutes at the boiling temperature. After this time, the dye bath is almost completely exhausted. The dyed material is rinsed and dried as usual. The fiber, which is colored in a greenish blue tone, is very lightfast, washable and decorative.
Den Farbstoff der angegebenen Formel erhält man durch Erhitzen von C.J. Basic Violet 3 (C.J. 42 555) in 80 bis zeiger Schwefelsäure und Oxidation des resultierenden Tris-(dimethylamino)-phenylfluorens durch Bleidioxid in Essigsäure.The dye of the formula given is obtained by heating C.J. Basic Violet 3 (C.J. 42 555) in 80 to show sulfuric acid and oxidation of the resulting tris (dimethylamino) phenylfluorene by lead dioxide in acetic acid.
Beispiel 2 In ein 60 0C warmes Färbebad aus 4000 Teilen Wasser, 2 Teilen Natriumacetat und 1 Teil Benzylpyridiniumchlorid trägt man 0,5 Teile des mit 3 Teilen 3obiger Essigsäure angeteigten rarbstoffes der Formel ein. Bei 800C gibt man 100 Teile Polyacrylnitrilfasern zu, steigert innerhalb von 45 Minuten die Temperatur auf 1000C und färbt 60 Minuten bei Kochtemperatur. Nach dieser Zeit ist das Färbebad fast völlig erschöpft. Das gefärbte Gut wird wie üblich gespült und getrocknet. Die grünstichig blaue Färbung ist sehr gut licht-, wasch- und dekaturecht.Example 2 In a 60 ° C. dyebath of 4000 parts of water, 2 parts of sodium acetate and 1 part of benzylpyridinium chloride, 0.5 part of the rare substance of the formula made into a paste with 3 parts of acetic acid is carried a. At 80 ° C., 100 parts of polyacrylonitrile fibers are added, the temperature is increased to 100 ° C. within 45 minutes and dyeing is carried out for 60 minutes at the boiling temperature. After this time, the dye bath is almost completely exhausted. The dyed material is rinsed and dried as usual. The greenish blue color is very fast to light, washing and decoration.
Der Farbstoff der angegebenen Formel wird durch Erhitzen von C.J. Basic Violet 4 (C.J. 42 600) in 9obiger Schwefelsäure und Oxidation des resultierenden Tris-(diäthylamino)-phenylfluorens durch Chioranil oder Bleidioxid in Essigsäure hergestellt.The dye of the formula given is prepared by heating C.J. Basic Violet 4 (C.J. 42 600) in the above sulfuric acid and oxidation of the resulting Tris- (diethylamino) -phenylfluorens by chioranil or lead dioxide in acetic acid manufactured.
Beispiel 3 In ein ungefähr 600C warmes Färbebad aus 4000 Teilen Wasser, 2 Teilen 96*der Schwefelsäure und 20 Teilen Glaubersalz gibt man 0,5 Teile des mit 1 bis 2 Teilen 3obiger Essigsäure angeteigten Farbetoffes der Formel Bei 800C bringt man dann 100 Teile Polyacrylnitrilfasern ein, steigert innerhalb von 30 Minuten die Temperatur auf 1000C und färbt 45 Minuten bei Kochtemperatur. Nach dieser Zeit ist das Färbebad fast völlig ausgezogen. Das gefärbte Gut wird wie üblich gespült und getrocknet. Die in marineblauer Nuance gefärbte Faser ist sehr gut licht-, wasch- und dekaturecht.EXAMPLE 3 0.5 part of the dyestuff of the formula made into a paste with 1 to 2 parts of the above acetic acid is added to a dyebath of 4000 parts of water, 2 parts of 96% sulfuric acid and 20 parts of Glauber's salt 100 parts of polyacrylonitrile fibers are then introduced at 80 ° C., the temperature is increased to 100 ° C. within 30 minutes and dyeing is carried out for 45 minutes at the boiling temperature. After this time, the dye bath is almost completely exhausted. The dyed material is rinsed and dried as usual. The fiber, dyed in a navy blue shade, is very resistant to light, washing and decoration.
Den Farbstoff erhält man durch Erhitzen von C.J. Basic Red 9 (C.J. 42 500) in 85 bis zeiger Schwefelsäure mit etwas Trinatriumphosphat und Oxidation des resultierenden Triaminophenylfluorens mit Bleidioxid in Essigsäure.The dye is obtained by heating C.J. Basic Red 9 (C.J. 42 500) in 85 bis sulfuric acid with a little trisodium phosphate and oxidation of the resulting triaminophenyl fluorene with lead dioxide in acetic acid.
Beispiel 4 In ein ungefähr 600C warmes Färbebad aus 4000 Teilen Wasser, 20 Teilen Glaubersalz und 1 Teil Dimethylfettalkyl-(bis C14)-benzylammoniumchlorid gibt man 0,5 Teile des Farbstoffes der Formel der mit 3 Teilen 30*iger Essigsäure angeteigt ist. Bei 80 0C gibt man 100 Teile Polyacrylnitrilfasern zu, steigert die Temperatur innerhalb von 45 Minuten auf 1000C und färbt 60 Minuten bei Kochtemperatur. Nach dieser Zeit ist das Färbebad fast völlig erschöpft. Das gefärbte Gut wird wie üblich gespült und getrocknet. Die. grünstichig blaue Färbung ist sehr gut licht-, wasch- und dekaturecht.EXAMPLE 4 0.5 part of the dye of the formula is added to a dyebath at about 600.degree. C. consisting of 4000 parts of water, 20 parts of Glauber's salt and 1 part of dimethyl fatty alkyl (up to C14) benzylammonium chloride which is made into a paste with 3 parts of 30% acetic acid. At 80 ° C., 100 parts of polyacrylonitrile fibers are added, the temperature is increased to 1000 ° C. within 45 minutes and dyeing is carried out for 60 minutes at the boiling temperature. After this time, the dye bath is almost completely exhausted. The dyed material is rinsed and dried as usual. The. The greenish blue color is very fast to light, washing and decoration.
Der Farbstoff wird durch Erhitzen von C.J. Basic Violet 1 (C.J. 42 535) in 85 bis 95*iger Schwefelsäure mit etwas Trinatriumphosphat und Oxidation des resultierenden Trisaminophenylfluorengemisches mit Bleidioxid in Essigsäure synthetisiert.The dye is made by heating C.J. Basic Violet 1 (C.J. 42 535) in 85 to 95% sulfuric acid with a little trisodium phosphate and oxidation of the resulting trisaminophenylfluorene mixture with lead dioxide in acetic acid synthesized.
Die folgenden Farbealze haben ähnliche färberische Eigenschaften: Nuance marineblau Nuance marineblau Sie wurden analog aus den entsprechenden Triphenylmethanfarbstoffen hergestellt und unter den gleichen Bedingungen gefärbt.The following color salts have similar coloring properties: Nuance navy blue Nuance navy blue They were prepared analogously from the corresponding triphenylmethane dyes and dyed under the same conditions.
Beispiel 5 In ein ungefähr 600C warmes Färbebad mit 4000 Teilen Wasser gibt man 20 Teile Glaubersalz, 1 Teil o-Phenylphenol und 0,5 Teile des Farbstoffes der Formel angeteigt mit 3 Teilen 30*iger Essigsäure. Bei 80°C bringt man dann mit 100 Teilen sauer modifizierter Polyesterfaser ein, steigert innerhalb von 30 Minuten die Temperatur auf 100 0C und färbt eine Stunde bei Kochtemperatur. Nach dieser Zeit ist das Färbebad fast völlig erschöpft. Das gefärbte Gut wird wie üblich gespült und getrocknet. Die grünstichig blaue Färbung hat gute Gebrauchsechtheiten.EXAMPLE 5 20 parts of Glauber's salt, 1 part of o-phenylphenol and 0.5 part of the dye of the formula are added to a dyebath at about 600.degree. C. with 4000 parts of water Made into a paste with 3 parts of 30% acetic acid. At 80 ° C., 100 parts of acid-modified polyester fibers are then introduced, the temperature is increased to 100 ° C. within 30 minutes and dyeing is carried out for one hour at the boiling temperature. After this time, the dye bath is almost completely exhausted. The dyed material is rinsed and dried as usual. The greenish blue color has good fastness properties.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702051318 DE2051318B2 (en) | 1970-10-20 | 1970-10-20 | PROCESS FOR COLORING SAUER MODIFIED TEXTILE MATERIAL MADE FROM POLYESTERS AND ACRYLNITRILE POLYMERISATES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702051318 DE2051318B2 (en) | 1970-10-20 | 1970-10-20 | PROCESS FOR COLORING SAUER MODIFIED TEXTILE MATERIAL MADE FROM POLYESTERS AND ACRYLNITRILE POLYMERISATES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2051318A1 true DE2051318A1 (en) | 1972-04-27 |
| DE2051318B2 DE2051318B2 (en) | 1972-07-20 |
Family
ID=5785585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702051318 Pending DE2051318B2 (en) | 1970-10-20 | 1970-10-20 | PROCESS FOR COLORING SAUER MODIFIED TEXTILE MATERIAL MADE FROM POLYESTERS AND ACRYLNITRILE POLYMERISATES |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2051318B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2823169A1 (en) * | 1978-05-26 | 1979-11-29 | Hoechst Ag | Tinting black polyacrylonitrile spinning compsns. - by addn. of blue or violet cationic or basic dyes which are resistant to migration |
| WO2001010840A1 (en) * | 1999-08-06 | 2001-02-15 | Henkel Kommanditgesellschaft Auf Aktien | Quaternized azafluorenones and their use in agents for dying fibers containing keratin |
-
1970
- 1970-10-20 DE DE19702051318 patent/DE2051318B2/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2823169A1 (en) * | 1978-05-26 | 1979-11-29 | Hoechst Ag | Tinting black polyacrylonitrile spinning compsns. - by addn. of blue or violet cationic or basic dyes which are resistant to migration |
| WO2001010840A1 (en) * | 1999-08-06 | 2001-02-15 | Henkel Kommanditgesellschaft Auf Aktien | Quaternized azafluorenones and their use in agents for dying fibers containing keratin |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2051318B2 (en) | 1972-07-20 |
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