EP0538714B2 - Biologisch abbaubare Faserpräparationsmittel - Google Patents

Biologisch abbaubare Faserpräparationsmittel Download PDF

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Publication number
EP0538714B2
EP0538714B2 EP92117479A EP92117479A EP0538714B2 EP 0538714 B2 EP0538714 B2 EP 0538714B2 EP 92117479 A EP92117479 A EP 92117479A EP 92117479 A EP92117479 A EP 92117479A EP 0538714 B2 EP0538714 B2 EP 0538714B2
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Prior art keywords
compounds
agents
fiber preparation
formula
treating agent
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Expired - Lifetime
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EP92117479A
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English (en)
French (fr)
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EP0538714B1 (de
EP0538714A1 (de
Inventor
Rolf Dr. Kleber
Lothar Jaeckel
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Clariant Produkte Deutschland GmbH
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Clariant GmbH
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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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/165—Ethers
    • D06M13/17—Polyoxyalkyleneglycol ethers
    • 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
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2904—Staple length fiber
    • Y10T428/2907—Staple length fiber with coating or impregnation
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer
    • Y10T428/2969—Polyamide, polyimide or polyester

Definitions

  • polyoxyalkylene glycols which are used in a heat treatment of prepared synthetic fibers, such as texturing, evaporate without residue, so that when used in Fiber preparation agents, the cleaning intervals of the texturing devices used are relatively long apart in time lie.
  • end-capped polyoxyalkylene glycols which have good properties, are known from EP-B-162 530 possess as a fiber preparation agent and also due to low residue formation on the fiber after heating processes.
  • biodegradable is to be understood to mean that the constituents of fiber preparation agents, such as lubricants, surfactants, thread-closing agents or even antistatic agents, are completely or at least 70% by weight in a biological way, for example by the enzymes or contained in the sewage sludge of a sewage treatment plant Bacteria are broken down.
  • the invention relates to the use of a fiber preparation agent, characterized by a content of compounds of the general formula HO (CH 2 CH 2 O) x -RO- (CH 2 CH 2 O) y H wherein R represents a 1-methylpropylene radical, 2-methylpropylene radical or a 1-methylethylene radical and the sum of x and y is 10 to 20, where x and y are different from zero, for fibers made of polyester, polyamides, polyacrylonitrile, polyolefins or the Copolymers of the aforementioned compounds.
  • the compounds of the formula I are well suited as fiber preparation agents.
  • the compounds of formula I are generally water-soluble or water-dispersible. They can be used as fiber preparation agents either alone or in a mixture with one another or with other fiber preparation agents known per se, such as surfactants, antistatic agents, such as P 2 O 5 ester salts, lubricants, such as ester oils or thread-locking agents, such as ethoxylated castor oils, which must also be biodegradable .
  • the fiber preparation agents can be applied from an aqueous solution, dispersion or emulsion, optionally with the use of suitable solvents or dispersing agents. Since most of the compounds of formula I are readily water-soluble, no additional emulsifiers are required when applied to the fiber, in contrast to mineral or ester oils.
  • the application is carried out according to the usual methods, for example by splashing or dipping. Spraying, padding or gear pumps.
  • polyester fibers e.g. Polyester fibers, Polyamides, polyacrylonitrile.
  • Polyolefins or the copolymers of the above compounds e.g. Polyester fibers, Polyamides, polyacrylonitrile.
  • Polyolefins or the copolymers of the above compounds e.g. Polyester fibers, Polyamides, polyacrylonitrile.
  • Polyolefins or the copolymers of the above compounds e.g. Polyester fibers, Polyamides, polyacrylonitrile.
  • the amount of glycol and alkaline catalyst are in a reaction vessel redesigned with a stirrer submitted. After purging with nitrogen to remove the oxygen, the mixture is heated to and at 120 to 125 ° C The temperature was kept under stirring under a water jet vacuum for 2 hours. After removing the water jet vacuum is heated to 130 to 140 ° C with stirring, whereupon the required at this temperature in a time of about 3 h Amount of gaseous ethylene oxide is metered in. The end of the ethylene oxide addition will decrease and essentially constant pressure recognizable. To clean the reaction product from any present volatile components this is for half an hour with stirring at about 80 ° C and a vacuum of 2 kPa held.
  • Table I summarizes the glycols and alkaline catalysts presented and the amount of ethylene oxide metered in at the reaction temperature and pressure.
  • Biodegradability is determined using the OECD 303 A test.
  • the biological elimination [% DOC] is determined depending on the time [d] (day, English: day). Table III shows the maximum biological elimination after 28 days.

Description

Aus US-A-4 179 544 und US-A-4 227 390 sind Polyoxyalkylenglykole bekannt, die bei einer Wärmebehandlung von präparierten Synthesefasern, wie dem Texturieren, rückstandslos verdampfen, so daß bei deren Verwendung in Faserpräparationsmitteln die Reinigungsintervalle der eingesetzten Texturiereinrichtungen zeitlich relativ lange auseinander liegen. Aus EP-B-162 530 sind sogenannte endverschlossene Polyoxyalkylenglykole bekannt, die gute Eigenschaften als Faserpräparationsmittel besitzen und sich ebenfalls durch geringe Rückstandsbildung auf der Faser nach Erhitzungsprozessen auszeichnen.
Aus EP-A- 0 189 804 sind propoxylierte Neopentylalkohole als Faserpräparationsmittel bekannt.
Alle diese Verbindungen zeigen jedoch den erheblichen Nachteil, daß sie biologisch nur mäßig abbaubar sind. In den letzten Jahren werden an Faserpräparationsmittel zusätzliche Bedingungen dahingehend gestellt, daß diese Mittel im Abwasser biologisch gut abbaubar sein sollen. Diese Bedingungen zielen darauf ab, die in die Abwässer von Textilbetrieben beim Färben oder Vorbehandeln gelangenden Faserpräparationsmittel durch biologischen Abbau zu eliminieren. Unter dem Begriff "biologisch abbaubar" ist zu verstehen, daß die Bestandteile von Faserpräparationsmitteln, wie Gleitmittel, Tenside, Fadenschlußmittel oder auch Antistatika vollständig oder zumindest zu 70 Gew.-% auf biologischem Weg, z.B. durch die in dem Klärschlamm einer Kläranlage enthaltenen Enzyme oder Bakterien, abgebaut werden. Dabei ist es wünschenswert, daß bei dem Abbau chemisch einfache Verbindungen, wie Kohlendioxid, Wasser, Sulfat oder Phosphat, entstehen.
Um die biologische Abbaubarkeit von chemischen Verbindungen beurteilen zu können, wurden eine Reihe von Testverfahren erarbeitet. Als geeignetes Verfahren zur Überprüfung der biologischen Abbaubarkeit von Faserpräparationsmitteln wird der "Coupled-Units-Test" (OECD-303-A-Test) genannt.
Die Bereitstellung biologisch abbaubarer Faserpräparationsmittel bereitet nach wie vor große Schwierigkeiten. Hier will die Erfindung Abhilfe schaffen.
Gegenstand der Erfindung ist die Verwendung eines Faserpräparationsmittels, gekennzeichnet durch einen Gehalt an Verbindungen der allgemeinen Formel HO(CH2CH2O)x-RO-(CH2CH2O)yH worin R für einen 1-Methylpropylenrest, 2-Methylpropylenrest oder einen 1-Methylethylenrest steht und die Summe von x und y 10 bis 20 beträgt, wobei x und y verschieden von Null sind, für Fasern aus Polyester, Polyamiden, Polyacrylnitril, Polyolefinen oder den Copolymeren der vorstehend genannten Verbindungen.
Die Herstellung dieser Verbindungen der Formel I erfolgt nach dem in der EP-B-166 958 beschriebenen Verfahren, indem ein Glykol mit Ethylenoxid umgesetzt wird.
Infolge ihrer unerwartet geringen Rückstandsbildung bei Erhitzungsprozessen, wie dem Texturieren, und ihrer überraschend guten biologischen Abbaubarkeit, eignen sich die Verbindungen der Formel I gut als Faserpräparationsmittel. Die Verbindungen der Formel I sind im allgemeinen wasserlöslich oder in Wasser dispergierbar. Sie können als Faserpräparationsmittel sowohl allein als auch in Mischung untereinander oder mit anderen an sich bekannten Faserpräparationsmitteln wie Tensiden, Antistatika, wie P2O5-Estersalzen, Gleitmitteln, wie Esterölen oder Fadenschlußmitteln, wie ethoxylierten Rizinusölen angewendet werden, die ebenfalls biologisch abbaubar sein müssen.
Bei Verwendung einer Mischung der Verbindungen der Formel I mit bekannten Faserpräparationsmitteln soll der Anteil der Verbindungen der Formel im Bereich von 10 bis 100 Gew.-Teilen, bezogen auf das Faserpräparationsmittel liegen. Bei der Präparation von Synthesefasern mit den Verbindungen der Formel I oder deren Mischungen soll die Auflage 0,1 bis 1 Gew.-%, bevorzugt 0,3 bis 0,5 Gew.-%, bezogen auf das Gewicht der Faser betragen, wobei die Verbindungen der Formel I entsprechend den vorstehend prozentualen Angaben in dem Faserpräparationsmittel enthalten sind.
Die Faserpräparationsmittel können aus wäßriger Lösung, Dispersion oder Emulsion, gegebenenfalls unter Mitverwendung geeigneter Löse- oder Dispergiermittel, aufgebracht werden.
Da die meisten Verbindungen der Formel I gut wasserlöslich sind, bedarf es bei dem Aufbringen auf die Faser, im Gegensatz zum Mineral oder Esterölen, keiner zusätzlichen Emulgatoren.
Das Aufbringen erfolgt nach den üblichen Methoden beispielsweise durch Pflatschen, Tauchen. Sprühen, Foulardieren oder Zahnradpumpen.
Als Synthesefasern, für die die Faserpräparationsmittel anzuwenden sind, kommen z.B. Fasern aus Polyestern, Polyamiden, Polyacrylnitril. Polyolefinen oder den Copolymeren der vorstehend genannten Verbindungen in Betracht.
Allgemeine Vorschrift zur Herstellung der nachfolgend genannten Acetale:
In einem mit Rührer umgestalteten Reaktionsgefäß werden die Menge von Glykol und alkalischem Katalysator vorgelegt. Nach Spülen mit Stickstoff zur Entfernung des Sauerstoffs wird auf 120 bis 125°C erhitzt und bei dieser Temperatur unter Rühren 2 h lang unter Wasserstrahlvakuum gehalten. Nach Wegnahme des Wasserstrahlvakuums wird unter Rühren auf 130 bis 140°C erhitzt, worauf bei dieser Temperatur in einer Zeit von etwa 3 h die erforderliche Menge gasförmiges Ethylenoxid zudosiert wird. Das Ende der Ethylenoxid-Zugabe wird am abfallenden und im wesentlichen konstant bleibende Druck erkennbar. Zur Reinigung des Reaktionsproduktes von gegebenenfalls anwesenden flüchtigen Anteilen wird dieses eine halbe Stunde lang unter Rühren bei etwa 80°C und einem Vakuum von 2 kPa gehalten.
In der nachstehenden Tabelle I sind die vorgelegten Glykole und alkalischen Katalysatoren sowie die bei der Reaktionstemperatur und dem Reaktionsdruck zudosierte Ethylenoxid-Menge zusammengefaßt.
Figure 00040001
Prüfung der Verstampfungsrate der Beispiele 1 bis 4:
Im Abdampftest werden jeweils 1 g der in Tabelle I aufgeführten Beispiele 1 bis 4 bei 220°C gehalten und die Verluste nach 0,33 Stunden (20 Minuten) und 24 Stunden beurteilt. Die prozentualen Verluste der Beispiele 1 bis 4 sind Tabelle II zu entnehmen.
Zeitdauer
Beispiel Nr. 20 Minuten 24 Stunden
1 9 % >95 %
2 8 % >95 %
3 7 % >95 %
4 6 % >95 %
Prüfung der biologischen Abbaubarkeit:
Die biologische Abbaubarkeit wird mit Hilfe des OECD 303 A-Testes ermittelt. Dabei wird die biologische Elimination [% DOC] in Abhängigkeit von der Zeit [d] (day, englisch: Tag) bestimmt.
Tabelle III gibt den Höchstwert der biologischen Elimination nach 28 Tagen an.
Beispiel Nr. Biologische Elimination [%] Zeit [d]
1 >90 % 28
2 >90 % 28
3 >90 % 28
4 >90 % 18

Claims (2)

  1. Verwendung eines Faserpräparationsmittels, gekennzeichnet durch einen Gehalt an Verbindungen der allgemeinen Formel HO(CH2CH2O)x-RO-(CH2CH2O)yH worin R für einen 1-Methylpropylenrest, 2-Methylpropylenrest oder einen 1-Methylethylenrest steht und die Summe von x und y 10 bis 20 beträgt, wobei x und y verschieden von Null sind, für Fasern aus Polyester, Polyamiden, Polyacrylnitril, Polyolefinen oder den Copolymeren der vorstehend genannten Verbindungen.
  2. Verwendung eines Faserpräparationsmittels nach Anspruch 1, dadurch gekennzeichnet, daß als weitere Bestandteile biologisch abbaubare Antistatika, Fadenschlußmittel und/oder Gleitmittel enthalten sind.
EP92117479A 1991-10-19 1992-10-13 Biologisch abbaubare Faserpräparationsmittel Expired - Lifetime EP0538714B2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4134610 1991-10-19
DE4134610 1991-10-19

Publications (3)

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EP0538714A1 EP0538714A1 (de) 1993-04-28
EP0538714B1 EP0538714B1 (de) 1997-03-12
EP0538714B2 true EP0538714B2 (de) 1999-09-01

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EP92117479A Expired - Lifetime EP0538714B2 (de) 1991-10-19 1992-10-13 Biologisch abbaubare Faserpräparationsmittel

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US (1) US5266221A (de)
EP (1) EP0538714B2 (de)
JP (1) JP3258724B2 (de)
KR (1) KR930008233A (de)
AR (1) AR247432A1 (de)
AT (1) ATE150108T1 (de)
BR (1) BR9204029A (de)
CA (1) CA2080741A1 (de)
DE (1) DE59208170D1 (de)
ES (1) ES2100997T5 (de)
MX (1) MX9205982A (de)
TR (1) TR26747A (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW225562B (de) * 1991-10-15 1994-06-21 Hoechst Ag
DE4304354A1 (de) * 1993-02-13 1994-08-18 Hoechst Ag Esterverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE4410708C1 (de) * 1994-03-28 1995-07-13 Hoechst Ag Präparationshaltige Aramidfasern und deren Verwendung
JP3045238B1 (ja) * 1999-03-24 2000-05-29 日華化学株式会社 繊維用処理油剤及び繊維の油剤処理方法
KR20160108856A (ko) 2015-03-09 2016-09-21 한국전자통신연구원 전자파 센서 및 전자파 센서의 생성 방법
CN115852683A (zh) * 2022-11-30 2023-03-28 上海丰泽源科技有限公司 一种可降解型pla纺丝油剂及其制备方法

Family Cites Families (14)

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Publication number Priority date Publication date Assignee Title
US4179544A (en) * 1977-12-05 1979-12-18 Basf Wyandotte Corporation Fiber finish compositions
US4256589A (en) * 1978-02-16 1981-03-17 Eastman Kodak Company Fiber treating compositions comprising (a) blend of random copoly(oxyethylene-oxypropylene)butanols (b) alkali metal sulfur compound and (c) alkali metal organic phosphate compound
DE2812443C2 (de) * 1978-03-22 1982-12-02 Hoechst Ag, 6000 Frankfurt Polyglykoläthermischformale sowie deren Verwendung als Faserpräparationsmittel
US4198464A (en) * 1978-05-26 1980-04-15 Basf Wyandotte Corporation Fiber lubricants based upon ethylene oxide capped polyethers of tetrahydrofuran and ethylene oxide
GB2109403B (en) * 1981-11-27 1985-07-17 Shell Int Research Alkoxylate textile processing oils
JPS60215873A (ja) * 1984-04-06 1985-10-29 竹本油脂株式会社 ポリエステル又はポリアミド繊維糸の紡糸油剤用組成物
DE3420708C1 (de) * 1984-06-02 1985-07-18 Hoechst Ag, 6230 Frankfurt Modifizierte Polyethylenglykole
US4622038A (en) * 1985-01-28 1986-11-11 Basf Corporation Low residue fiber spin finishes
US4789381A (en) * 1987-04-27 1988-12-06 Kao Corporation Fiber treating process and composition used therefor
DE3723349C1 (de) * 1987-07-15 1988-08-11 Goldschmidt Ag Th Mittel zum Ausruesten von Fasern oder Faserprodukten
US5066414A (en) * 1989-03-06 1991-11-19 The Procter & Gamble Co. Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
DE3936975C1 (en) * 1989-11-07 1991-01-24 Tudapetrol Mineraloelerzeugnisse Nils Hansen Kg, 2000 Hamburg, De Spooling oil to treat textured fibres or yarns - comprises vegetable oil, ester of vegetable fatty acid, fatty alcohol polyglycol ether, fatty alcohol methacrylate, etc.
US5079076A (en) * 1990-03-15 1992-01-07 The Lubrizol Corporation Composition and polymer fabrics treated with the same
US5126060A (en) * 1991-01-09 1992-06-30 Colgate-Palmolive Co. Biodegradable fabric softening compositions based on pentaerythritol esters and free of quaternary ammonium compounds

Also Published As

Publication number Publication date
AR247432A1 (es) 1994-12-29
US5266221A (en) 1993-11-30
TR26747A (tr) 1995-05-15
ES2100997T3 (es) 1997-07-01
ES2100997T5 (es) 1999-12-01
KR930008233A (ko) 1993-05-21
JP3258724B2 (ja) 2002-02-18
BR9204029A (pt) 1994-03-22
CA2080741A1 (en) 1993-04-20
EP0538714B1 (de) 1997-03-12
MX9205982A (es) 1993-04-01
ATE150108T1 (de) 1997-03-15
DE59208170D1 (de) 1997-04-17
EP0538714A1 (de) 1993-04-28
JPH05279924A (ja) 1993-10-26

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