EP0075261B1 - Preparing agent for fibres - Google Patents

Preparing agent for fibres Download PDF

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Publication number
EP0075261B1
EP0075261B1 EP82108493A EP82108493A EP0075261B1 EP 0075261 B1 EP0075261 B1 EP 0075261B1 EP 82108493 A EP82108493 A EP 82108493A EP 82108493 A EP82108493 A EP 82108493A EP 0075261 B1 EP0075261 B1 EP 0075261B1
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European Patent Office
Prior art keywords
alkyl
fiber
amine oxides
preparation
agents
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Expired
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EP82108493A
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German (de)
French (fr)
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EP0075261A2 (en
EP0075261A3 (en
Inventor
Rolf Dr. Kleber
Norbert Dr. Wester
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Hoechst AG
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Hoechst AG
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    • 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
    • D06M13/322—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 nitrogen
    • D06M13/388—Amine oxides
    • 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

Definitions

  • preparation agents in the production of filament threads from synthetic polymers is well known and has been sufficiently described.
  • a major problem here is the use of antistatic agents, since the components of the preparation must be sufficiently thermostable, especially in filament preparations intended for use on fast-running processing machines. It is known, for example, that classic filament preparations without the addition of antistatic agents exhibit problems with static charging when stretch texturing.
  • thermostable antistatic agents for example a quaternization product of the reaction product of diethylaminoethanol with 10 mol of ethylene oxide and 20 mol of propylene oxide.
  • the thermal test (230-235 0 C / 24 h.) Indeed shows that these products form only a few residues, but even the remaining residues are too high and can contaminate the heater, especially as the possibly solid residues through reaction with thread guide elements can also cause thread breaks.
  • the amine oxides described in DE-A-23 26 966 have proven themselves well in preparation formulations, especially in combinations with low-volatility lubricants, they give the threads good antistatic properties and are to be regarded as thermostable. However, they often have too high a volatility in short-term heating processes, so that when these amine oxides are used alone, the problem of vaporization from the thread can occur too quickly.
  • amine oxides based on an oxyalkylated C 4 -C 4 alcohol is also known from EP-A-22 239.
  • the agents for liquid paraffin waxing described therein mainly contain paraffin and polyglycol ether and, in addition, even smaller amounts of these amine oxides.
  • the invention thus relates to fiber preparation agents which, in addition to the components usually contained in fiber preparation agents, also contain an amine oxide of the formula where R, C 4 ⁇ C 22 alkyl or C 4 ⁇ C 22 alkenyl, preferably C 10 ⁇ C 16 alkyl, R 2 is hydrogen and / or methyl, where hydrogen and methyl can alternate, R 3 and R 4 C, -C 4 alkyl and X is a number from 1 to 20, preferably 3 to 10, contain.
  • chain-pure alkyl compounds instead of the chain-pure alkyl compounds, it is of course also possible in any case to use compounds whose alkyl groups represent technical sections, the average number of carbon atoms corresponding to or coming close to the abovementioned alkyl radicals.
  • the alkyl residues accumulating from natural long-chain fatty acids are particularly preferred since the corresponding alcohols with one or two long-chain alkyl residues are commercially available and the amine oxides are thus easily accessible.
  • the numerical value X is generally an average value, since technical oxyalkylation generally results in product mixtures. This also applies to the oxethylates listed here for the sake of simplicity.
  • amine oxides described above are used as antistatic agents in conventional preparation agents.
  • these preparation agents usually consist of approx. 20 to 60% by weight of a lubricant such as, for example, ester oils, mineral oils, end-capped oxethylates, propylene-ethylene oxide copolymers, 0-50% by weight emulsifier, for example fatty alcohol oxyethylates, 0-30% by weight.
  • a lubricant such as, for example, ester oils, mineral oils, end-capped oxethylates, propylene-ethylene oxide copolymers, 0-50% by weight emulsifier, for example fatty alcohol oxyethylates, 0-30% by weight.
  • % other antistakics for example P 2 0 r , esters of fatty alcohols and 1-50% by weight of the amine oxides.
  • the amine oxides can be used in combination with thread-locking agents (oxyethylated castor oils, sarcosides, POCI 3 esters) and sliding components (phosphoric acid esters).
  • thread-locking agents oxyethylated castor oils, sarcosides, POCI 3 esters
  • sliding components phosphoric acid esters
  • the amine oxides show a high antistatic effect even in relatively low doses.
  • the required quantities fluctuate depending on the type and quantity of the components (oil, emulsifier) and can be easily determined by simple preliminary tests.
  • the favorable properties of the amine oxides in the preparation are particularly evident on synthetic fibers such as those made of polyester, polyamide 6, polyamide 6,6, polyacrylonitrile or polyolefin.
  • a polyester yarn dtex 300 f 32 matt is spun at 2800m / min, prepared with 12% preparations and on a stretch texturing machine using the friction process on dtex 167 at 800 m / min. stretch textured.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Der Einsatz von Präparationsmitteln bei der Herstellung von Filamentfäden aus synthetischen Polymeren ist gut bekannt und ausreichend beschrieben. Ein großes Problem hierbei ist der Einsatz von Antistatika, da besonders bei Filamentpräpationen, die zum Einsatz auf schnell laufenden Verarbeitungsmaschinen gedacht sind, die Komponenten des Präparationsmittels ausreichend thermostabil sein müssen. So ist bekannt, daß klassische Filamentpräparationen ohne Zusatz von Antistatika beim Strecktexturieren Problems hinsichtlich der statischen Aufladung zeigen.The use of preparation agents in the production of filament threads from synthetic polymers is well known and has been sufficiently described. A major problem here is the use of antistatic agents, since the components of the preparation must be sufficiently thermostable, especially in filament preparations intended for use on fast-running processing machines. It is known, for example, that classic filament preparations without the addition of antistatic agents exhibit problems with static charging when stretch texturing.

Das Zumischen bekannter Antistatika, wie Phosphorsäureester, Alkansulfonate, Sarkoside, quaternäre Amoniumverbindungen führt zwar bereits in geringen Mengen zur Beseitigung dieser Problems, doch neigen diese schwerflüchtigen Verbindungen bereits in geringen Konzentrationen beim Erhitzen zum Vercracken, Verkohlen und damit zur Bildung teerartiger Rückstände.The admixing of known antistatic agents, such as phosphoric acid esters, alkanesulfonates, sarcosides, quaternary ammonium compounds leads to the elimination of this problem in small amounts, but these low-volatility compounds, even in low concentrations, tend to crack, carbonize and thus to form tar-like residues.

Versuche, diese Nachteile zu überwinden, sind aus der EP-A-13820 behannt. Dort werden als thermostabile Antistatika alkoxylierte Derivate des Alkanolamins beschrieben, z.B. ein Quaternisierungsprodukt des Umsetzungsprodukts von Diethylaminoethanol mit 10 Mol Ethylenoxid und 20 Mol Propylenoxid. Der Thermotest (230-2350C/24 h.) zeigt in der Tat, daß diese Produkte nur wenige Rückstände bilden, doch selbst die verbleidenden Rückstände sind zu hoch und können die Heizer verschmutzen, zumal die evtl. festen Rückstände durch Reaktion mit Fadenleitorganen noch zusätzlich Fadenbrüche bewirken können. Die in der DE-A-23 26 966 beschriebenen Aminoxide haben sich in Präperationsformulierungen besonders in Kombinationen mit schwerflüchtigen Gleitmitteln gut bewährt, sie verleihen den Fäden gute Antistatikeigenschaften und sind als thermostabil anzusehen. Sie weisen jedoch häufig eine zu hohe Flüchtigkeit bei Kurzzeiterhitzungsprozessen auf, so daß bei alleinigem Einsatz dieser Aminoxide das Problem des zu schnellen Verdampfens vom Faden auftreten kann.Attempts to overcome these disadvantages are known from EP-A-13820. There, alkoxylated derivatives of alkanolamine are described as thermostable antistatic agents, for example a quaternization product of the reaction product of diethylaminoethanol with 10 mol of ethylene oxide and 20 mol of propylene oxide. The thermal test (230-235 0 C / 24 h.) Indeed shows that these products form only a few residues, but even the remaining residues are too high and can contaminate the heater, especially as the possibly solid residues through reaction with thread guide elements can also cause thread breaks. The amine oxides described in DE-A-23 26 966 have proven themselves well in preparation formulations, especially in combinations with low-volatility lubricants, they give the threads good antistatic properties and are to be regarded as thermostable. However, they often have too high a volatility in short-term heating processes, so that when these amine oxides are used alone, the problem of vaporization from the thread can occur too quickly.

Die Verwendung von Aminoxiden auf der Basis eines oxalkylierten C,-C4-Alkohols mit auch aus der EP-A-22 239 bekannt. Die dort beschriebenen Mittel zum Flüssigparaffinieren von Garnen enthalten zur Hauptsache Paraffin und Polyglykoläther und daneben noch geringere Mengen dieser Aminoxide.The use of amine oxides based on an oxyalkylated C 4 -C 4 alcohol is also known from EP-A-22 239. The agents for liquid paraffin waxing described therein mainly contain paraffin and polyglycol ether and, in addition, even smaller amounts of these amine oxides.

Es zeigte sich nun, daß es gelingt, zu Aminoxiden der gewünschten niederen Kurzeitflüchtigkeit zu kommen, die jedoch im Langzeittest rückstandslos sich zersetzen, wenn man Aminoxide einsetzt, die eine oxalkylierte C4―C22-Alkyl- oder Alkenyl-Gruppe enthalten.It has now been shown that it is possible to obtain amine oxides of the desired low short-term volatility, which, however, decompose without residue in the long-term test if amine oxides are used which contain an oxyalkylated C 4 -C 22 -alkyl or alkenyl group.

Gegenstand der Erfindung sind somit Faserpräparationsmittel, die neben den überlicherweise in Faserpräparationsmitteln enthaltenen Komponenten noch ein Aminoxid der Formel

Figure imgb0001
wobei R, C4―C22-Alkyl oder C4―C22-Alkenyl, vorzugsweise C10―C16-Alkyl, R2 Wasserstoff und/oder Methyl, wobei Wasserstoff und Methyl alternieren können, R3 und R4 C,-C4-Alkyl und X eine Zahl von 1 bis 20, vorzugsweise 3 bis 10 bedeutet, enthalten.The invention thus relates to fiber preparation agents which, in addition to the components usually contained in fiber preparation agents, also contain an amine oxide of the formula
Figure imgb0001
 where R, C 4 ―C 22 alkyl or C 4 ―C 22 alkenyl, preferably C 10 ―C 16 alkyl, R 2 is hydrogen and / or methyl, where hydrogen and methyl can alternate, R 3 and R 4 C, -C 4 alkyl and X is a number from 1 to 20, preferably 3 to 10, contain.

Diese Aminoxide sind aus NL-A-70 15 335 und JP―A―72 13 016 bekannt. Sie werden erhalten nach bekannten Verfahren, indem man oxalkylierte langkettige Alkohole der Formel

Figure imgb0002
chloriert, beispielsweise mit Thionylchlorid. Die dabei erhaltenen Chloride werden anschließend mit sekundären Aminen der Formel
Figure imgb0003
umgesetzt und die Reaktionsprodukte dann mit H202 oxidiert. Als oxalkylierte langkettige Alkohole kommen vorzugsweise Cocostettalkohol mit 5 Einheiten Ethylenoxid, Oleylalkohol mit 7 Einheiten Ethylenoxid in Frage, aber auch die folgenden Verbindungen:

  • C4H9 · (EO)10 · (Py0),o - H und
  • Pentaerythrit - (EO)5 · (PyO)5
  • (EO=Ethylenoxid, PyO=Propylenoxid)
These amine oxides are known from NL-A-70 15 335 and JP ― A ― 72 13 016. They are obtained by known methods by using oxyalkylated long chain alcohols of the formula
Figure imgb0002
 chlorinated, for example with thionyl chloride. The chlorides obtained are then with secondary amines of the formula
Figure imgb0003
 implemented and the reaction products then oxidized with H 2 0 2 . Possible alkoxylated long-chain alcohols are preferably coco fatty alcohol with 5 units of ethylene oxide, oleyl alcohol with 7 units of ethylene oxide, but also the following compounds:
  • C 4 H 9 · (EO) 10 · (Py0), o - H and
  • Pentaerythritol - (EO) 5 · (P y O) 5
  • (EO = Ethylene no xid, P y O = Propylene oxide)

Weitere Beispiele der Aminoxide sind

Figure imgb0004

  • R=75% C10/14-Alkyl
  • 25% i―C10/14-Alkyl
    Figure imgb0005
    Figure imgb0006
Other examples of the amine oxides are
Figure imgb0004
  • R = 75% C 10/14 alkyl
  • 25% i ― C 10/14 alkyl
    Figure imgb0005
    Figure imgb0006

Selbstverständlich können an Stelle der kettenreinen Alkylverbindungen in jedem Falle auch Verbindungen verwendet werden, deren Alkylgruppe technische Schnitte darstellen, wobei deren durchschnittliche Zahl von C-Atomen den obengenannten Alkylresten entspricht oder nahekommt. Die sich von natürlichen langkettigen Fettsäuren anbeitenden Alkylreste sind besonders bevorzugt, da die entsprechenden Alkohole mit einem oder zwei langkettigen Alkylresten handelsüblich und die Aminoxide somit leicht zugänglich sind.Instead of the chain-pure alkyl compounds, it is of course also possible in any case to use compounds whose alkyl groups represent technical sections, the average number of carbon atoms corresponding to or coming close to the abovementioned alkyl radicals. The alkyl residues accumulating from natural long-chain fatty acids are particularly preferred since the corresponding alcohols with one or two long-chain alkyl residues are commercially available and the amine oxides are thus easily accessible.

Bei dem Zahlenwert X handelt es sich im allgemeinen um Durchschnittswerte, da die technische Oxalkylierung generell Produktgemische ergibt. Dies gilt auch für die hier aufgeführten-der Einfachheit halber als einheitlich formulierten-Oxäthylate.The numerical value X is generally an average value, since technical oxyalkylation generally results in product mixtures. This also applies to the oxethylates listed here for the sake of simplicity.

Die oben beschriebenen Aminoxide werden in üblichen Präparationsmitteln als Antistatika eingesetzt. Bei Filamentsystemen bestehen diese Präparationsmittel üblicherweise aus ca. 20 bis 60 Gew.-% eines Gleitmittels wie zum Beispiel Esteröle, Mineralöle, endverschlossene Oxethylate, Propylen-Ethylenoxidcopolymere, 0-50 Gew.-% Emulgator, z.B. Fettalkoholoxethylate, 0-30 Gew.-% andere Antistakika z.B. P20r,-Ester von Fettalkoholen und 1-50 Gew.-% der Aminoxide.The amine oxides described above are used as antistatic agents in conventional preparation agents. In filament systems, these preparation agents usually consist of approx. 20 to 60% by weight of a lubricant such as, for example, ester oils, mineral oils, end-capped oxethylates, propylene-ethylene oxide copolymers, 0-50% by weight emulsifier, for example fatty alcohol oxyethylates, 0-30% by weight. % other antistakics, for example P 2 0 r , esters of fatty alcohols and 1-50% by weight of the amine oxides.

Bei Fasern können die Aminoxide in Kombination mit Fadenschlußmitteln (oxethylierte Rizinusöle, Sarkoside, POCI3-Ester) und Gleitkomponenten (Phosphorsäureester) eingesetzt werden.In the case of fibers, the amine oxides can be used in combination with thread-locking agents (oxyethylated castor oils, sarcosides, POCI 3 esters) and sliding components (phosphoric acid esters).

Die Aminoxide zeigen schon in verhältnismäßig geringer Dosierung eine hohe antistatische Wirkung. Die erforder lichen Einsatzmengen schwanken je nach Art und Menge der übringen Komponenten (Öl, Emulgator) und lassen sich durch einfache Vorversuche leicht ermitteln. Üblicherweise werden 0,05 bis 1,5%, vorzugsweise 0,05 bis 1%, bezogen auf das Gewicht des Substrats, aufgebracht.The amine oxides show a high antistatic effect even in relatively low doses. The required quantities fluctuate depending on the type and quantity of the components (oil, emulsifier) and can be easily determined by simple preliminary tests. Usually 0.05 to 1.5%, preferably 0.05 to 1%, based on the weight of the substrate, is applied.

Hervorzuheben ist die geringe Flüchtigkeit dieser Verbindungen, die einen Einsatz auch bei hohen Temperaturen und in sehr schnell laufenden Aggregaten erlauben.Of particular note is the low volatility of these compounds, which allow use even at high temperatures and in very fast-running units.

Die günstigen Eigenschaften der Aminoxide im Präparationsmittel kommen insbesondere auf Synthesefasern wie solchen aus Polyester, Polyamid 6, Polyamid 6,6, Polyacrylnitril oder Polyolefin zur Geltung.The favorable properties of the amine oxides in the preparation are particularly evident on synthetic fibers such as those made of polyester, polyamide 6, polyamide 6,6, polyacrylonitrile or polyolefin.

BeispieleExamples

102,5 g (0,25 mol) C12-15-Isoalkylpentaoxiethylalkohol werden nach bekannten Verfahren nacheinander mit Thionylchlorid, Dimethylamin und H202 umgesetzt. Man erhält 340 g (90% d. Theorie) einer 30% igen wässrigen Lösung des Aminoxids der Formel

Figure imgb0007
102.5 g (0.25 mol) of C 12-15 isoalkylpentaoxyethyl alcohol are reacted in succession with thionyl chloride, dimethylamine and H 2 0 2 by known processes. 340 g (90% of theory) of a 30% strength aqueous solution of the amine oxide of the formula are obtained
Figure imgb0007

In analoger Weise wurden folgende Verbindungen hergestellt

Figure imgb0008
Figure imgb0009
Figure imgb0010
Figure imgb0011
6) Cokosalkyldimethylaminoxid (Vergleich nach DE-A-23 26 966)The following compounds were prepared in an analogous manner
Figure imgb0008
Figure imgb0009
Figure imgb0010
Figure imgb0011
 6) cocoalkyldimethylamine oxide (comparison according to DE-A-23 26 966)

Flüchtigkeitstest und Prüfung auf TeerbildungVolatility test and tar formation test

  • Einwaage: 1 g der 30 %igen wässrigen LösungenWeigh-in: 1 g of the 30% aqueous solutions
  • Erhitzungstemperatur: 230°CHeating temperature: 230 ° C

Flüchtigkeit der Aktivsubstanz in Prozent Vergilbung nach DIN 6162 (Jodfarbskala) Teerbildung (Rückstand)

Figure imgb0012
Gleiche Effekte zeigen die Produkte
Figure imgb0013
Figure imgb0014
 Volatility of the active substance in percent yellowing according to DIN 6162 (iodine color scale) tar formation (residue)
Figure imgb0012
 The products show the same effects
Figure imgb0013
Figure imgb0014

Ein Polyestergarn dtex 300 f 32 matt wird bei 2800m/min ausgesponnen, mit 12 %igen Präparationen präpariert und auf einer Strecktexturiermaschine nach dem Friktionsverfahren auf dtex 167 bei 800 m/min. strecktexturiert.A polyester yarn dtex 300 f 32 matt is spun at 2800m / min, prepared with 12% preparations and on a stretch texturing machine using the friction process on dtex 167 at 800 m / min. stretch textured.

Folgende Präparationen werden eingesetzt

Figure imgb0015
The following preparations are used
Figure imgb0015

Die Spinnspulenbildung erfolgte für die Systeme problemlos (Präparationsauflage: 0,35%). Der nachfolgende Strecktexturierprozeß ergab für

  • 1) geringe Heizerverschmutzung, wenig Flusen
  • 2) hohe Heizerverschmutzung, mittlere Flusen
  • 3a) keine Heizerverschmutzung, keine Flusen
  • 3b) keine Heizerverschmutzung, keine Flusen

im testurierten Garn.The spinning bobbin formation was easy for the systems (preparation run: 0.35%). The subsequent stretch texturing process resulted in
  • 1) low heater pollution, little fluff
  • 2) high heater pollution, medium lint
  • 3a) no heater pollution, no fluff
  • 3b) no heater pollution, no fluff

in the certified yarn.

Die Tests zeigen, daß Faserpraparationsmittel mit nicht-ethoxylierten Aminoxiden gemäß dem Stand der Technik zwar eine geringe Neigung zeigen, Rückstände zu bilden und somit recht thermostabil sind, doch sind sie recht flüchtig im Vergleich zu den Faserpräparationsmitteln mit erfindungsgemäßen Aminoxiden auf der Basis von oxalkylierten Alkoholen, die sowohl thermostabil sind als auch nichtflüchtig.The tests show that fiber preparation agents with non-ethoxylated amine oxides according to the prior art have a low tendency to form residues and are therefore quite thermostable, but they are quite volatile in comparison to the fiber preparation agents with amine oxides according to the invention based on oxalkylated alcohols that are both thermally stable and non-volatile.

Claims (3)

1. Fiber preparation compositions containing the components usually used in such compositions which additionally contain an amine oxide of the formula
Figure imgb0018
in which R, denotes C4―C22-alkyl or C4―C22-alkenyl, preferably C10―C16-alkyl, R2 denotes hydrogen and/or methyl, it being possible for hydrogen and methyl to alternate, R3 and R4 denote C1―C4-alkyl and X denotes a number from 1 to 20, preferably 3 to 10.
2. A process for the preparation of textile fibers, which comprises applying a fiber preparation composition as claimed in claim 1 to the textile fiber.
3. A process as claimed in claim 2, wherein such an amount of the fiber preparation composition is applied to the textile fiber that a concentration of 0.05 to 1.5% by weight of the amine oxide referred to the weight of the fiber, is obtained.
EP82108493A 1981-09-17 1982-09-15 Preparing agent for fibres Expired EP0075261B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813136941 DE3136941A1 (en) 1981-09-17 1981-09-17 FIBER PREPARATION AGENTS
DE3136941 1981-09-17

Publications (3)

Publication Number Publication Date
EP0075261A2 EP0075261A2 (en) 1983-03-30
EP0075261A3 EP0075261A3 (en) 1985-01-30
EP0075261B1 true EP0075261B1 (en) 1987-04-15

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EP (1) EP0075261B1 (en)
JP (1) JPS5860067A (en)
DE (2) DE3136941A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4025731A1 (en) * 1990-08-14 1992-02-20 Henkel Kgaa TEXTILE EQUIPMENT
AT396930B (en) * 1992-01-23 1993-12-27 Chemiefaser Lenzing Ag AMINOXIDE
DE19755047A1 (en) * 1997-12-11 1999-06-17 Hoechst Trevira Gmbh & Co Kg Nonwovens of electret fibers with improved charge stability, prepared fiber, preferably electret fiber, process for their preparation and their use
CN114775276B (en) * 2022-05-30 2023-03-10 宁波润禾高新材料科技股份有限公司 Durable amphoteric aliphatic liquid hydrophilic softener and preparation method thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2000142A1 (en) * 1968-01-11 1969-08-29 Armour Ind Chem Co
NL7015335A (en) * 1970-10-20 1971-03-25 Low density washing powders
DE2927027A1 (en) * 1979-07-04 1981-01-08 Hoechst Ag AGENT FOR LIQUID PARAFFINING YARN

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DE3136941A1 (en) 1983-04-14
EP0075261A2 (en) 1983-03-30
DE3276076D1 (en) 1987-05-21
JPS5860067A (en) 1983-04-09
EP0075261A3 (en) 1985-01-30

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