DE1031274B - Process for improving the colorability of molded articles made of polyesters based on terephthalic acid - Google Patents
Process for improving the colorability of molded articles made of polyesters based on terephthalic acidInfo
- Publication number
- DE1031274B DE1031274B DEF21669A DEF0021669A DE1031274B DE 1031274 B DE1031274 B DE 1031274B DE F21669 A DEF21669 A DE F21669A DE F0021669 A DEF0021669 A DE F0021669A DE 1031274 B DE1031274 B DE 1031274B
- Authority
- DE
- Germany
- Prior art keywords
- terephthalic acid
- improving
- colorability
- molded articles
- polyesters based
- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 12
- 229920000728 polyester Polymers 0.000 title claims description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000002926 oxygen Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000986 disperse dye Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- -1 cyclohexilformamide Chemical compound 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IIBOGKHTXBPGEI-UHFFFAOYSA-N N-benzylformamide Chemical compound O=CNCC1=CC=CC=C1 IIBOGKHTXBPGEI-UHFFFAOYSA-N 0.000 description 1
- SWGXDLRCJNEEGZ-UHFFFAOYSA-N N-cyclohexylformamide Chemical compound O=CNC1CCCCC1 SWGXDLRCJNEEGZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
- D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
-
- 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
- D06P1/64—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 using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65143—Compounds containing acid anhydride or acid halide 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
- 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
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
- D06P1/67375—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341 with sulfur-containing anions
-
- 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
-
- 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
- D06P3/54—Polyesters using dispersed dyestuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/04—Polyester fibers
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Es ist bereits bekannt, die Anfärbbarkeit von Polyestermaterialien auf Terephthalsäurebasis durch Behandeln derselben mit Polyglykoläthern von Aminen bei Temperaturen oberhalb 100° C zu verbessern. Bei diesem Verfahren wird eine Umesterung des Materials erzielt, wobei basische Stickstoffatome in das Polyestermolekül eingebaut werden. Ferner ist es bereits bekannt, die Anfärbbarkeit von Polyestermaterial auf Terephthalsäurebasis dadurch zu verbessern, daß man das Polyestermaterial abwechselnd mit starken anorganischen Säuren und hochkonzentrierten wässerigen Ammoniaklösungen behandelt. Weiterhin hat man bereits zur Verbesserung derartiger Materialien empfohlen, Sulfurylchlorid auf das Material einwirken zu lassen und das so behandelte Produkt mit wässerigen Lösungen von anorganischem Alkali nachzuwaschen.It is already known that polyester materials based on terephthalic acid can be dyed Treating the same with polyglycol ethers of amines at temperatures above 100 ° C to improve. In this process, a transesterification of the material is achieved, leaving basic nitrogen atoms be incorporated into the polyester molecule. Furthermore, it is already known that the dyeability of To improve polyester material based on terephthalic acid by alternating the polyester material with strong inorganic acids and highly concentrated aqueous ammonia solutions treated. Sulfuryl chloride has also been recommended to improve such materials to act on the material and the thus treated product with aqueous solutions to wash off inorganic alkali.
Gegenstand des Patents 1006 383 ist ein Verfahren zur Verbesserung der Anfärbbarkeit von geformten Gebilden aus Polyestern auf Terephthalsäurebasis mit Schwefeltrioxyd und bzw. oder Halogeniden von Sauerstoffsäuren des Schwefels, wobei man die Behandlung der Gebilde in inerten Lösungsmitteln vornimmt, vorzugsweise bei erhöhter Temperatur. The subject of patent 1006 383 is a method to improve the dyeability of molded structures made of terephthalic acid-based polyesters with sulfur trioxide and / or halides of oxo acids of sulfur, wherein the structures are treated in inert solvents, preferably at elevated temperature.
In weiterer Ausgestaltung dieses Verfahrens wurde nun gefunden, daß man zu einer Verbesserung der Anfärbbarkeit von geformten Gebilden aus Polyestern auf Terephthalsäurebasis, insbesondere PoIyäthylenglykolterephthalat, gelangt, wenn man die gemäß dem Verfahren des Hauptpatentes veredelten Gebilde mit N-Formylverbindungen behandelt, die wenigstens ein Wasserstoffatom an dem die Formylgruppe tragenden Stickstoffatom besitzen.In a further embodiment of this process it has now been found that an improvement in the Dyeability of molded structures made of terephthalic acid-based polyesters, in particular polyethylene glycol terephthalate, if you treat the fabric refined according to the process of the main patent with N-formyl compounds, the have at least one hydrogen atom on the nitrogen atom bearing the formyl group.
Als derartige N-Formylverbindungen seien beispielsweise genannt: Formamid und dessen durch aliphatische. cycloaliphatische, araliphatische Reste substituierte Derivate, wie Äthylformamid, Cyclohexilformamid, Benzylformamid, Di-(N-formyl)-äthylendiamin, Di-(N-formyl)-hexamethylendiamin. Vorzugsweise werden diese Verbindungen in verdünntem Zustand, d. h. in Lösung, angewandt. Als Lösungsmittel kommen solche Verbindungen in Betracht, die unter den Versuchsbedingungen mit einer Formylgruppe nicht reagieren, z. B. aliphatische Alkohole, wie Methanol oder Äthanol, Ketone, wie Aceton, Äther, wie Diäthyläther, Ester, wie Essigsäureäthylester, aliphatische oder cycloaliphatische Kohlenwasserstoffe wie Hexan, Cyclohexan oder Leichtbenzin, Halogenkohlenwasserstoffe, wie Tetrachlorkohlenstoff. Chloroform, Methylenchlorid oder Äthylenchlorid. Aus Gründen der Einfachheit und Billigkeit wird man aber bevorzugt Wasser als Lösungsmittel verwenden.Examples of such N-formyl compounds include: formamide and its through aliphatic. cycloaliphatic, araliphatic radicals substituted derivatives, such as ethylformamide, cyclohexilformamide, Benzylformamide, di- (N-formyl) -ethylenediamine, di- (N-formyl) -hexamethylenediamine. Preferably these compounds are used in a diluted state, i.e. H. in solution. as Solvents such compounds come into consideration, which under the test conditions with a Formyl group do not react, e.g. B. aliphatic alcohols such as methanol or ethanol, ketones, such as Acetone, ethers such as diethyl ether, esters such as ethyl acetate, aliphatic or cycloaliphatic Hydrocarbons such as hexane, cyclohexane or mineral spirits, halogenated hydrocarbons such as carbon tetrachloride. Chloroform, methylene chloride or ethylene chloride. For the sake of simplicity and Cheap but one will prefer to use water as a solvent.
Verfahren zur VerbesserungProcess for improvement
der Anfärbbarkeit von geformten Gebilden aus Polyestern auf Terephthalsäurebasisthe dyeability of molded structures made of terephthalic acid-based polyesters
Zusatz zum Patent 1 006 383Addendum to patent 1 006 383
Anmelder:Applicant:
Farbwerke Hoechst AktiengesellschaftFarbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning,formerly Master Lucius & Brüning,
Frankfurt/M., Brüningstr. 45Frankfurt / M., Brüningstr. 45
Dr. Adolf Hartmann, Gessertshausen bei Augsburg,Dr. Adolf Hartmann, Gessertshausen near Augsburg,
und Dr. Wilhelm Happe, Bad Schwalbach (Taunus),and Dr. Wilhelm Happe, Bad Schwalbach (Taunus),
sind als Erfinder genannt wordenhave been named as inventors
Die Nachbehandlung erfolgt im allgemeinen bei erhöhter Temperatur. Üblicherweise wird man die Behandlung in der siedenden Lösung durchführen. Die Konzentration der Lösungen kann in weiten Grenzen schwanken; sie richtet sich nach der chemischen Konstitution der Formylverbindungen, nach der Behandlungsdauer und -temperatur und dem gewünschten Effekt. Im allgemeinen wird man die Konzentration so wählen, daß die Behandlungsdauer in dem für einen kontinuierlichen Fabrikationsbetrieb geeigneten Bereich liegt. So wird man üblicherweise mit 0,1- bis lOVoigen, vorzugsweise 0,5 bis 5°/oigen, wässerigen Lösungen arbeiten. Es genügt dann eine Behandlungsdauer von 2 bis 5 Minuten, wenn man eine Temperatur von etwa 98 bis 100° C wählt. Wendet man tiefere Temperaturen an, so ist die Behandlungsdauer auszudehnen und bzw. oder die Konzentration zu erhöhen.The aftertreatment is generally carried out at an elevated temperature. Usually one becomes the Perform treatment in the boiling solution. The concentration of the solutions can vary widely Boundaries fluctuate; it depends on the chemical constitution of the formyl compounds the duration and temperature of the treatment and the desired effect. Generally one gets the concentration choose so that the treatment time in that for a continuous manufacturing operation suitable range. So you will usually with 0.1 to 10%, preferably 0.5 to 5%, aqueous solutions work. A treatment time of 2 to 5 minutes is sufficient if you selects a temperature of about 98 to 100 ° C. If lower temperatures are used, the duration of the treatment must be extended and / or the concentration to increase.
Es ist selbstverständlich möglich, verschiedene Formylverbindungen gleichzeitig anzuwenden und, den Flotten Stoffe zuzugeben, die in an sich bekannter Weise als Quellmittel wirken, z. B. Phenylglykol, Kresylglykol, Dioxan, Benzoesäurebenzylester, gegebenenfalls unter Mitverwendung eines geeigneten Emulgators.It is of course possible to use different formyl compounds at the same time and, to add the liquors substances that act in a known manner as swelling agents, eg. B. Phenylglycol, Cresyl glycol, dioxane, benzyl benzoate, optionally with the use of a suitable one Emulsifier.
Die gemäß dem Verfahren der vorliegenden Erfindung behandelten geformten Gebilde aus Polyestern auf Terephthalsäurebasis zeichnen sich durch eine verbesserte Anfärbbarkeit aus. Die mit basischen undThe molded articles of polyester treated according to the method of the present invention based on terephthalic acid are distinguished by improved colorability. The ones with basic and
809 529/453809 529/453
insbesondere Dispersionsfarbstoffen, wie sie in dem Hauptpatent genannt sind, erzielten Färbungen sind hinsichtlich Bügelbeständigkeit, Lichtechtheit und typkonformer Nuance weiter verbessert.in particular disperse dyes, as mentioned in the main patent, are the colorations achieved Further improved in terms of ironing resistance, lightfastness and type-conforming shade.
Ein vefstrecktes Spinnkabel aus Polyäthylenglykolterephthalat mit einem Gesamtster von 20 000 den, welches nach dem im Hauptpätent geschilderten Verfahren mit dem Addukt aus Dioxan und Schwefeltrioxyd in Methylenchlorid behandelt war, wird durch eine 5°/oige wässerige Lösung von Formamid bei 98° C mit einer solchen Geschwindigkeit geführt, daß die Verweilzeit in der Lösung 3 Minuten beträgt. Dann wird mit Wasser von Raumtemperatur kurz gespült und wie üblich präpariert und getrocknet. Nach Kräuselung und Schnitt erhält man eine Faserflocke, die sich mit zahlreichen Dispersionsfarbstoffen ohne Anwendung von Quellmitteln · oder überatmosphärischem Druck tief und echt anfärben läßt. Die Nuancen der Färbungen entsprechen den auf unbehandeltem Material mit Hilfe von Quellmitteln oder bei Färbetemperaturen über 100° C erzielten Farbtönen, die Färbungen sind hitzebeständig und besitzen gute Lichtechtheit.A stretched tow made of polyethylene glycol terephthalate with a total of 20,000 den, which according to the procedure described in the main patent was treated with the adduct of dioxane and sulfur trioxide in methylene chloride, is passed through a 5% aqueous solution of formamide at 98 ° C at such a rate, that the residence time in the solution is 3 minutes. Then with water at room temperature Rinsed briefly and prepared and dried as usual. After crimping and cutting, a fiber flock is obtained, which deal with numerous disperse dyes without the use of swelling agents · or superatmospheric Print can be stained deep and real. The nuances of the dyeings correspond to those on untreated Material obtained with the help of swelling agents or at dyeing temperatures above 100 ° C Color shades, the colorations are heat-resistant and have good lightfastness.
Eine Faserflocke aus Polyäthylenglykolterephthalat (Einzeltiter 3 den), deren Anfärbbarkeit nach dem Verfahren des Hauptpatents verbessert wurde, wird anschließend mit einer 3%>igen wässerigen Lösung von N-Formylcyclohexylamin 3 Minuten bei 95° C nachbehandelt. Die Flocke wird dann mit Wasser gespült und getrocknet. Sie läßt sich mit Dispersionsfarbstoffen sehr gut färben, die Färbungen besitzen eine gute Hitzebeständigkeit und Lichtechtheit.A fiber flake made of polyethylene glycol terephthalate (single titer 3 den), the colorability of which according to the The process of the main patent has been improved, then with a 3% aqueous solution of N-formylcyclohexylamine for 3 minutes at 95 ° C post-treated. The flake is then rinsed with water and dried. It can be colored very well with disperse dyes which have colorations good heat resistance and lightfastness.
Ein nach dem Verfahren des Hauptpatents hinsichtlich Anfärbbarkeit verbessertes Spinnkabel aus Polyäthylenglykolterephthalat wird mit einer 2°/oigen Lösung von Äthylformamid in Äthylenchlorid während 5 Minuten bei Rückflußtemperatur behandelt. Man trocknet in einem Heißluftstrom und verfährt weiter, wie im Beispiel 1 beschrieben. Die erhaltene Faser zeichnet sich durch eine sehr gute Anfärbbarkeit für zahlreiche Dispersionsfarbstoffe aus, die Färbungen sind bügelecht und in der Nuance typkonform.A tow improved according to the process of the main patent with regard to dyeability Polyethylene glycol terephthalate is treated with a 2% solution of ethyl formamide in ethylene chloride treated for 5 minutes at reflux temperature. Dry in a stream of hot air and proceed continue as described in example 1. The fiber obtained is characterized by very good dyeability for numerous disperse dyes, the dyeings are iron-resistant and the shade conforms to the type.
Claims (1)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE555688D BE555688A (en) | 1956-03-10 | ||
| NL96674D NL96674C (en) | 1956-03-10 | ||
| DEF19763A DE1006383B (en) | 1956-03-10 | 1956-03-10 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF19938A DE1014958B (en) | 1956-03-10 | 1956-03-31 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF21669A DE1031274B (en) | 1956-03-10 | 1956-11-15 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| US643947A US2989363A (en) | 1956-03-10 | 1957-03-05 | Process for improving the dyeability of shaped structures of polyesters based on terephthalic acid |
| FR1172936D FR1172936A (en) | 1956-03-10 | 1957-03-09 | Method for improving dyeability of polyester articles |
| GB7998/57A GB855546A (en) | 1956-03-10 | 1957-03-11 | Process for improving the dyeing capacity of fibres or films of polyesters based on terephthalic acid |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF19763A DE1006383B (en) | 1956-03-10 | 1956-03-10 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF19938A DE1014958B (en) | 1956-03-10 | 1956-03-31 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF21669A DE1031274B (en) | 1956-03-10 | 1956-11-15 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1031274B true DE1031274B (en) | 1958-06-04 |
Family
ID=27210040
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF19763A Pending DE1006383B (en) | 1956-03-10 | 1956-03-10 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF19938A Pending DE1014958B (en) | 1956-03-10 | 1956-03-31 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF21669A Pending DE1031274B (en) | 1956-03-10 | 1956-11-15 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF19763A Pending DE1006383B (en) | 1956-03-10 | 1956-03-10 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
| DEF19938A Pending DE1014958B (en) | 1956-03-10 | 1956-03-31 | Process for improving the colorability of molded articles made of polyesters based on terephthalic acid |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2989363A (en) |
| BE (1) | BE555688A (en) |
| DE (3) | DE1006383B (en) |
| FR (1) | FR1172936A (en) |
| GB (1) | GB855546A (en) |
| NL (1) | NL96674C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO102217L (en) * | 1955-06-30 | |||
| DE1068008B (en) * | 1958-02-26 | 1959-10-29 | Kalk &. Co. Aktiengesellschaft, Wiesbaden-Biebrich | Process for increasing the adhesion of sheet-like structures made from polyterephthalic acid glycol esters |
| DE1132890B (en) * | 1959-07-30 | 1962-07-12 | Hoechst Ag | Process for improving the dyeability of fiber structures made of polyesters of terephthalic acid with 1,4-dihydroxymethyl-cyclohexane |
| BE604720A (en) * | 1960-06-09 | |||
| US3253880A (en) * | 1961-10-09 | 1966-05-31 | Chemstrand Corp | Sulfonation of acrylonitrile polymers with sulfur trioxide to increase dye receptivity |
| NL122994C (en) * | 1961-10-19 | |||
| BE632939A (en) * | 1962-08-08 | |||
| US3460896A (en) * | 1964-10-14 | 1969-08-12 | Eastman Kodak Co | Polyester fibers having improved hydrophilicity as a result of modification with phosphoric acid,phosphorous acid or perchloric acid |
| US3617338A (en) * | 1969-10-20 | 1971-11-02 | Dow Chemical Co | Method for producing a latent striated effect on plastic films |
| CN110924188B (en) * | 2019-12-06 | 2022-05-20 | 常熟市江南印染有限公司 | One-bath short-period low-water dyeing process for pretreatment dyeing of polyester fabric |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB613818A (en) * | 1945-06-07 | 1948-12-03 | James Gordon Napier Drewitt | Improvements in the treatment of textile and other materials having a basis of cellulose derivatives or synthetic resins |
| GB613817A (en) * | 1945-06-07 | 1948-12-03 | James Gordon Napier Drewitt | Improvements in the production or treatment of cellulose derivative or synthetic resin materials |
| GB697657A (en) * | 1950-06-14 | 1953-09-30 | Calico Printers Ass Ltd | Improvements relating to the processing of highly polymeric linear polyester materials |
| GB697986A (en) * | 1950-11-27 | 1953-10-07 | Denys Nicol Marvin | Improvements in dyeing polyester filaments, yarns and fabrics |
| US2647104A (en) * | 1951-07-30 | 1953-07-28 | Du Pont | Linear polyester composition |
| US2852554A (en) * | 1956-07-12 | 1958-09-16 | Du Pont | Alpha-sulfopolyfluoromonocarboxylic acids and derivatives hydrolyzable thereto |
| US2849458A (en) * | 1957-04-01 | 1958-08-26 | Du Pont | Production of sulfonates |
-
0
- BE BE555688D patent/BE555688A/xx unknown
- NL NL96674D patent/NL96674C/xx active
-
1956
- 1956-03-10 DE DEF19763A patent/DE1006383B/en active Pending
- 1956-03-31 DE DEF19938A patent/DE1014958B/en active Pending
- 1956-11-15 DE DEF21669A patent/DE1031274B/en active Pending
-
1957
- 1957-03-05 US US643947A patent/US2989363A/en not_active Expired - Lifetime
- 1957-03-09 FR FR1172936D patent/FR1172936A/en not_active Expired
- 1957-03-11 GB GB7998/57A patent/GB855546A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1006383B (en) | 1957-04-18 |
| GB855546A (en) | 1960-12-07 |
| BE555688A (en) | 1957-03-30 |
| NL96674C (en) | |
| DE1014958B (en) | 1957-09-05 |
| FR1172936A (en) | 1959-02-17 |
| US2989363A (en) | 1961-06-20 |
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