EP0149116A2 - Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur - Google Patents
Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur Download PDFInfo
- Publication number
- EP0149116A2 EP0149116A2 EP84114978A EP84114978A EP0149116A2 EP 0149116 A2 EP0149116 A2 EP 0149116A2 EP 84114978 A EP84114978 A EP 84114978A EP 84114978 A EP84114978 A EP 84114978A EP 0149116 A2 EP0149116 A2 EP 0149116A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyacrylonitrile
- alkyl
- retarder
- acrylonitrile copolymers
- 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.)
- Withdrawn
Links
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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- 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
Definitions
- the compounds (I) are prepared by known processes from unsaturated fatty acids or from mixtures of saturated and unsaturated fatty acids, for example mixtures obtained from natural fats, or from their esters or chlorides and the unsymmetrical dialkylalkylenediamines.
- the amidamines are then again quaternized by known processes using quaternizing agents such as benzyl chloride, methyl, ethyl, butyl chloride, dimethyl and diethyl sulfate and dimethyl methane phosphoric acid.
- quaternizing agents such as benzyl chloride, methyl, ethyl, butyl chloride, dimethyl and diethyl sulfate and dimethyl methane phosphoric acid.
- oleic acid, soy oleic acid Suitable for palm kernel acid, poppy oil acid, sunflower oil acid, rapeseed acid and tallow fatty acid.
- Unsymmetrical alkylated alkylenediamines for example N, N-dimethyl-ethylenediamine, NN-diethylethylenediamine, N, N-dimethyl-propylenediamine and N, N-diethyl-propylenediamine, are to be mentioned as diamines.
- Suitable cationic dyes are dyes of the most varied classes of compounds, for example diphenylmethane, triphenylmethane and rhodamine dyes, azo or anthraquinone dyes containing onium groups, furthermore thiazine, oxazine, methine and azomethine dyes, as described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 3 Edition 1970, supplement volume p. 225 are described.
- the required amounts of the compounds of formula (I) to be used according to the invention can easily be determined by preliminary tests. In general, amounts of about 0.25 to 2.5%, based on the weight of the dye material used, of these compounds are used.
- Suitable Acrylnitrilmischpolymerisate are for example copolymers of Acyrlnitril with vinyl chloride, vinylidene chloride, vinyl acetate, vinyl chloroacetate, vinyl alcohol, acrylic and methacrylic acid, Acyrl and methacrylic acid esters, allyl or basi - specific vinyl compounds such as vinyl imidazole, Vinylbenzimidazol, vinylpyridine, Vinylmethylpyridin, vinylpyrimidine, the proportion provided that Co-monomers is not more than 20 percent by weight.
- the dyeing of the polyacrylonitrile fiber materials can be carried out in the customary manner in the exhaust process by introducing the material to be dyed into an aqueous dye liquor heated to about 50-85 ° C. which contains the cationic dye, compounds of the formula (I), additions of salts such as sodium acetate or Sodium sulfate, also contains acids such as acetic acid or formic acid, then the temperature of the dyebath is raised to approximately 100 ° C. in the course of about 30 minutes and then the dyebath is kept at this temperature until it is exhausted.
- the material to be dyed can also be pretreated at a temperature of 40-100 ° C.
- fiber materials consisting of polyacrylonitrile or acrylonitrile-containing copolymers or containing such copolymers or copolymers, which can be present in various processing stages, for example as spun tow, sliver, flakes, threads, yarns, woven or knitted fabrics, are excellently uniform and to color in deep tones.
- DE-A-1 127 865 discloses the use of retarders of the formula (I), in which R 1 is a saturated aliphatic hydrocarbon radical when dyeing with poly fiber materials containing acrylonitrile are known.
- R 1 is a saturated aliphatic hydrocarbon radical when dyeing with poly fiber materials containing acrylonitrile are known.
- a compound with R 1 C 11 H 23 b eschrie- ben.
- ammonium compounds (I) of the present invention ß compared to the corresponding saturated derivatives have improved activity as retarder, so that one can operate with smaller amounts of auxiliaries. In general, 3-4 times the amount of saturated ammonium compound is required to achieve comparable effectiveness.
- the dyeing curve of the dyes has a uniform slope with a constant temperature increase in the drawing phase.
- the compounds prepared according to the following examples show a band at 6.1-6.25 p in the IR spectrum.
- the effectiveness against the corresponding ammonium compound from stearic acid is about 3 times.
- 250 g of palm kernel fatty acid are converted into the fatty acid amine amine using 114 g of N, N-diethylethylenediamine.
- the quaternization is carried out by mixing with excess butyl chloride by heating in an autoclave at 100 ° C. for 1 hour, at 120 ° C. for 1 hour and at 130 ° C. for 2 hours. Excess butyl chloride is then stripped off with steam. A slightly water-soluble product is obtained.
- Example 4 Of a substance produced by the process described in Example 4 from the coconut fat consisting of over 95% saturated fatty acid glycerides, three times the amount of the compound of Example 4 is required in order to achieve the same retarding effect.
- Example 4 400 g of the tallow fatty acid amidamine used in Example 4 are reacted with 100 g of butyl chloride at 110 ° C. in an autoclave for 6 hours. The pressure initially increased to 2 bar drops to 0.3 bar towards the end of the reaction.
- the quaternary compound obtained is readily soluble in water and shows an activity which is three times as great on both dry-spun and wet-spun acrylic fibers as that of the compound prepared from the correspondingly hydrogenated tallow fat.
- Yarn made of polyacrylonitrile fibers is introduced in a liquor ratio of 1:40 into a bath heated to 80 ° C., which contains 0.06 g of a cationic dye of the formula in liters
- a knitted fabric made from staple polyacrylonitrile fibers is introduced in a liquor ratio of 1:15 into a bath at 85 ° C., which contains 0.3 g of a dye of the formula
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3345900 | 1983-12-20 | ||
DE19833345900 DE3345900A1 (de) | 1983-12-20 | 1983-12-20 | Verfahren zum faerben von fasermaterialien aus polyacrylnitril oder acrylnitrilmischpolymerisaten und retarder enthaltende mittel |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0149116A2 true EP0149116A2 (fr) | 1985-07-24 |
EP0149116A3 EP0149116A3 (fr) | 1985-08-14 |
Family
ID=6217376
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84114978A Withdrawn EP0149116A3 (fr) | 1983-12-20 | 1984-12-08 | Procédé de teinture de matières fibreuses à base de polyacrylonitrile ou de copolymères d'acrylonitrile et produit auxiliaire contenant un retardateur |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0149116A3 (fr) |
JP (1) | JPS60151390A (fr) |
DE (1) | DE3345900A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0327379A2 (fr) * | 1988-02-05 | 1989-08-09 | CRODA INTERNATIONAL plc | Humectants |
WO1993002042A1 (fr) * | 1991-07-18 | 1993-02-04 | Eastman Kodak Company | Sels d'ammonium quaternaires contenant un amide |
WO1997034041A1 (fr) * | 1996-03-11 | 1997-09-18 | High Point Chemical Corporation | Composes d'unisson biodegradables pour fibres acryliques |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2963339A (en) * | 1960-12-06 | Retarding and levelling agents | ||
GB866335A (en) * | 1956-07-31 | 1961-04-26 | Ciba Ltd | Process for the dyeing of fibres of polyacrylonitrile |
GB969855A (en) * | 1960-01-14 | 1964-09-16 | Sandoz Ltd | Process for the level dyeing of natural or synthetic polyamide fibres |
JPS444609Y1 (fr) * | 1965-06-18 | 1969-02-19 | ||
DE2430853A1 (de) * | 1974-06-27 | 1976-01-08 | Cassella Farbwerke Mainkur Ag | Hilfsmittel zum egalen faerben von gebilden aus polyacrylnitril oder sauer modifizierten polyestern |
DE2548009A1 (de) * | 1974-10-29 | 1976-05-06 | Ciba Geigy Ag | Verfahren zum egalen faerben von langsam-, normal- und schnellziehenden polyacrylnitrilmaterialien |
EP0105034A1 (fr) * | 1982-09-27 | 1984-04-04 | Ciba-Geigy Ag | Adjuvant de teinture et procédé pour la teinture de fibres en matériel polyacrylonitrilique |
-
1983
- 1983-12-20 DE DE19833345900 patent/DE3345900A1/de not_active Withdrawn
-
1984
- 1984-12-08 EP EP84114978A patent/EP0149116A3/fr not_active Withdrawn
- 1984-12-17 JP JP59264661A patent/JPS60151390A/ja active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2963339A (en) * | 1960-12-06 | Retarding and levelling agents | ||
GB866335A (en) * | 1956-07-31 | 1961-04-26 | Ciba Ltd | Process for the dyeing of fibres of polyacrylonitrile |
GB969855A (en) * | 1960-01-14 | 1964-09-16 | Sandoz Ltd | Process for the level dyeing of natural or synthetic polyamide fibres |
JPS444609Y1 (fr) * | 1965-06-18 | 1969-02-19 | ||
DE2430853A1 (de) * | 1974-06-27 | 1976-01-08 | Cassella Farbwerke Mainkur Ag | Hilfsmittel zum egalen faerben von gebilden aus polyacrylnitril oder sauer modifizierten polyestern |
DE2548009A1 (de) * | 1974-10-29 | 1976-05-06 | Ciba Geigy Ag | Verfahren zum egalen faerben von langsam-, normal- und schnellziehenden polyacrylnitrilmaterialien |
EP0105034A1 (fr) * | 1982-09-27 | 1984-04-04 | Ciba-Geigy Ag | Adjuvant de teinture et procédé pour la teinture de fibres en matériel polyacrylonitrilique |
Non-Patent Citations (1)
Title |
---|
DERWENT JAPANESE PATENTS REPORT, Band 8, Nr. 8, 1969, Sektion 2, Seite 3; & JP-Y-44 004 609 (MORIN KAGAKU KOGYO CO., LTD.) 25.02.1969 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0327379A2 (fr) * | 1988-02-05 | 1989-08-09 | CRODA INTERNATIONAL plc | Humectants |
EP0327379A3 (fr) * | 1988-02-05 | 1991-01-09 | CRODA INTERNATIONAL plc | Humectants |
WO1993002042A1 (fr) * | 1991-07-18 | 1993-02-04 | Eastman Kodak Company | Sels d'ammonium quaternaires contenant un amide |
WO1997034041A1 (fr) * | 1996-03-11 | 1997-09-18 | High Point Chemical Corporation | Composes d'unisson biodegradables pour fibres acryliques |
Also Published As
Publication number | Publication date |
---|---|
DE3345900A1 (de) | 1985-06-27 |
JPS60151390A (ja) | 1985-08-09 |
EP0149116A3 (fr) | 1985-08-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
17P | Request for examination filed |
Effective date: 19841208 |
|
AK | Designated contracting states |
Designated state(s): DE FR GB IT |
|
AK | Designated contracting states |
Designated state(s): DE FR GB IT |
|
17Q | First examination report despatched |
Effective date: 19860430 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
18W | Application withdrawn |
Withdrawal date: 19860729 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: BOEHMKE, GUENTHER, DR. Inventor name: JAKOBS, KARLHANS, DIPL.-ING. |