EP0046507B1 - Oiling agent for synthetic fibres, and its use - Google Patents

Oiling agent for synthetic fibres, and its use Download PDF

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Publication number
EP0046507B1
EP0046507B1 EP81105655A EP81105655A EP0046507B1 EP 0046507 B1 EP0046507 B1 EP 0046507B1 EP 81105655 A EP81105655 A EP 81105655A EP 81105655 A EP81105655 A EP 81105655A EP 0046507 B1 EP0046507 B1 EP 0046507B1
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EP
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Prior art keywords
formula
alkyl
denotes
alkenyl
oiling agent
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EP81105655A
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German (de)
French (fr)
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EP0046507A1 (en
Inventor
Rolf Dr. Kleber
Dieter Dr. Plabst
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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
    • 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
    • D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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

  • the invention thus relates to a preparation agent for synthetic fibers, which is an amine oxide of the formula 1 contains, wherein R, C 5 -C 22 alkyl, preferably C 10 -C 16 alkyl or C 5 -C 22 alkenyl, preferably C 10 -C 16 alkenyl, R 2 is a group of formula 2 R 3 C, and Cs - C 22 alkyl, preferably Cio - C 16 alkyl, Cs - C 22 alkenyl, preferably C 10 ⁇ C 16 alkenyl or a group of formula 2, X either methyl and Y hydrogen or X Hydrogen and Y are methyl and n and m are numbers from 1 to 8, the sum of n and m not being greater than 10.
  • the groups R i , R 2 and R 3 are chosen within the definitions given above so that the amine oxide is soluble in water.
  • Preferred amine oxides include
  • amine oxides are prepared by known processes by oxyalkylation of mono- or dialkylamines and subsequent oxidation, for example with hydrogen peroxide.
  • the oxalkylation can be carried out by first adding ethylene oxide and then propylene oxide or vice versa. Products with blocks of oxipropylene and oxiethylene units are then obtained.
  • the amines can also be alkoxylated with a mixture of different compositions of ethylene oxide and propylene oxide.
  • compounds with polyoxyalkyl groups are then obtained in which the oxipropylene and oxiethylene units are randomly distributed according to the ratio of ethylene oxide to propylene oxide.
  • n and m are generally average values, since technical oxyalkylation generally gives product mixtures. This also applies to the oxethylates listed here - for the sake of simplicity as uniformly formulated.
  • amine oxides are used in preparation agents for synthetic fibers such as polyester, polyamide, polyacrylonitrile or polyolefin fibers.
  • Preparations of this type usually consist of 0-50% by weight of oils such as ester oils or mineral oils, 0-60% by weight of emulsifier such as, for example, ethylated fatty alcohols, 0-60% by weight of a lubricant such as, for example, water-soluble end-capped oxyethylates, ethylene oxide-propylene oxide Copolymers or their ethers with fatty alcohols, 0-30% by weight of an antistatic such as, for example, esters of P 2 0 5 and fatty alcohols or ethoxylated fatty alcohols, and 1 to 50, preferably 5-20% by weight, of one or more of the amine oxides described above .
  • oils such as ester oils or mineral oils
  • emulsifier such as, for example, ethylated fatty alcohols
  • the amine oxides show a high antistatic effect even in relatively low doses.
  • the required quantities vary depending on the type and quantity of the other components (oil, emulsifier) and can be easily determined by simple preliminary tests. Usually 0.01 to 2%, preferably 0.05 to 1%, based on the weight of the substrate, is applied.
  • preparation agents according to the invention are described in their composition, which contain an amine oxide of formula 1.
  • the percentages are percentages by weight.

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

Description

Aus der DE-PS 2326966 ist bereits bekannt, Aminoxide mit Polyethylenoxidgruppen in Präparationsmitteln für Synthesefasern einzusetzen. Im Zuge der Entwicklung neuerer Verfahren zum Texturieren von Synthesefasern wird jedoch verlangt, daß die Präparationsmittel selbst thermostabil, d. h. schwerflüchtig sind und sich außerdem bei Verstreckprozessen oder beim Strecktexturierprozeß, also bei einem kurzzeitigen Hitzekontakt, nicht zersetzen, daß aber abgeriebene oder abgestreifte bzw. abgetropfte Präparationsrückstände auf den Heizaggregaten, Verstreckgaletten, Fixiereinrichtungen, Heizern von Texturiereinrichtungen nicht zu Vercrackungen, Verkohlungen oder teerartigen Rückständen führen. Diese teerartigen Verkohlungsrückstände können in der Tat zu Beschädigungen der präparierten Fäden führen und Kapillar- bzw. Fadenbrüche bewirken. Besonders problematisch ist es, für solche Präparationsmittel nicht verkohlende Antistatika zu finden, die in Verbindung mit den anderen Bestandteilen des Präparationsmittels eine befriedigende antistatische Wirkung zeigen. Die in der DE-PS 2 326 966 beschriebenen Aminoxide sind zwar thermostabil, jedoch zeigte sich, daß sie beim längeren Einwirken von Hitze die obenerwähnten teerartigen Verkohlungsrückstände bilden.From DE-PS 2326966 it is already known to use amine oxides with polyethylene oxide groups in preparation agents for synthetic fibers. In the course of the development of newer methods for texturing synthetic fibers, however, it is required that the preparation agents themselves are thermostable, i.e. H. are not volatile and also do not decompose in stretching processes or in the stretch texturing process, i.e. in the event of brief contact with heat, but that rubbed off or stripped or drained preparation residues on the heating units, stretching godets, fixing devices, heaters of texturing devices do not lead to cracking, charring or tar-like residues. These tar-like charring residues can indeed damage the prepared threads and cause capillary or thread breaks. It is particularly problematic to find non-carbonizing antistatic agents for such preparation agents which, in combination with the other components of the preparation agent, have a satisfactory antistatic effect. Although the amine oxides described in DE-PS 2 326 966 are thermostable, it has been shown that they form the above-mentioned tar-like charring residues when exposed to heat for a prolonged period.

Es stellte sich daher die Aufgabe, Antistatika zu entwickeln, die selbst thermostabil sind, sich mit den Gleitmittelkomponenten gut mischen und beim längeren Erhitzen auf hohe Temperaturen keine teerartigen Verkohlungsrückstände bilden.It was therefore the task to develop antistatic agents which are themselves thermally stable, mix well with the lubricant components and do not form tar-like charring residues when heated for a long time at high temperatures.

Es wurde nun gefunden, daß diese Bedingungen erfüllt werden von solchen oxalkylierten Aminoxiden, die keine reine Polyethylenoxidkette enthalten, sondern eine gemischte Ethylenoxid- und Propylenoxidkette.It has now been found that these conditions are met by those oxyalkylated amine oxides which do not contain a pure polyethylene oxide chain but a mixed ethylene oxide and propylene oxide chain.

Gegenstand der Erfindung ist somit ein Präparationsmittel für Synthesefasern, das ein Aminoxid der Formel 1

Figure imgb0001
enthält, wobei R, C5-C22-Alkyl, vorzugsweise C10-C16-Alkyl oder C5-C22-Alkenyl, vorzugsweise C10-C16-Alkenyl, R2 eine Gruppe der Formel 2
Figure imgb0002
R3 C, sowie Cs - C22-Alkyl, vorzugsweise Cio - C16-Alkyl, Cs - C22-Alkenyl, vorzugsweise C10 ―C16-Alkenyl oder eine Gruppe der Formel 2, X entweder Methyl und Y Wasserstoff oder X Wasserstoff und Y Methyl und n und m Zahlen von 1 bis 8 bedeuten, wobei die Summe von n und m nicht größer als 10 sein soll.The invention thus relates to a preparation agent for synthetic fibers, which is an amine oxide of the formula 1
Figure imgb0001
 contains, wherein R, C 5 -C 22 alkyl, preferably C 10 -C 16 alkyl or C 5 -C 22 alkenyl, preferably C 10 -C 16 alkenyl, R 2 is a group of formula 2
Figure imgb0002
 R 3 C, and Cs - C 22 alkyl, preferably Cio - C 16 alkyl, Cs - C 22 alkenyl, preferably C 10 ―C 16 alkenyl or a group of formula 2, X either methyl and Y hydrogen or X Hydrogen and Y are methyl and n and m are numbers from 1 to 8, the sum of n and m not being greater than 10.

Die Gruppen Ri, R2 und R3 werden innerhalb der oben angegebenen Definitionen so gewählt, daß das Aminoxid in Wasser löslich ist. Bevorzugte Aminoxide sind unter anderem

Figure imgb0003
Figure imgb0004
 The groups R i , R 2 and R 3 are chosen within the definitions given above so that the amine oxide is soluble in water. Preferred amine oxides include
Figure imgb0003
Figure imgb0004

Die Herstellung dieser Aminoxide erfolgt nach bekannten Verfahren durch Oxalkylierung von Mono-oder Dialkylaminen und anschließende Oxydation etwa mit Wasserstoffperoxid. Bei der Oxalkylierung kann man so vorgehen, daß man zunächst Ethylenoxid und dann Propylenoxid addiert oder umgekehrt. Man erhält dann Produkte mit Blöcken von Oxipropylen- und Oxiethylen-Einheiten. Man kann die Amine aber auch mit einem Gemisch unterschiedlicher Zusammensetzung von Ethylenoxid und Propylenoxid oxalkylieren. Man erhält dann, wie bekannt, Verbindungen mit Polyoxialkylgruppen, in denen die Oxipropylen- und Oxiethylen-Einheiten statistisch verteilt sind entsprechend dem Verhältnis Ethylenoxid zu Propylenoxid.These amine oxides are prepared by known processes by oxyalkylation of mono- or dialkylamines and subsequent oxidation, for example with hydrogen peroxide. The oxalkylation can be carried out by first adding ethylene oxide and then propylene oxide or vice versa. Products with blocks of oxipropylene and oxiethylene units are then obtained. However, the amines can also be alkoxylated with a mixture of different compositions of ethylene oxide and propylene oxide. As is known, compounds with polyoxyalkyl groups are then obtained in which the oxipropylene and oxiethylene units are randomly distributed according to the ratio of ethylene oxide to propylene oxide.

Bei den Mono- oder Di-alkylaminen 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 obengeannten Alkylresten entspricht oder nahekommt. Die sich von natürlichen langkettigen Fettsäuren ableitenden Alkylreste sind besonders bevorzugt, da die entsprechenden tertiären Amine mit einem oder zwei langkettigen Alkylresten handelsüblich und die Aminoxide somit leicht zugänglich (oder ebenfalls handelsüblich) sind. Da diese nativen Fettalkylreste vielfach mehr oder weniger große Mengen an ungesättigten Anteilen enthalten, umfaßt die Formel 1 neben den Alkylaminoxiden auch die entsprechenden Alkenylaminoxide.In the case of the mono- or di-alkylamines, instead of the chain-pure alkyl compounds it is also possible in any case to use compounds whose alkyl groups represent technical sections, the average number of carbon atoms corresponding to or approximating the alkyl radicals mentioned above. The alkyl radicals derived from natural long-chain fatty acids are particularly preferred since the corresponding tertiary amines with one or two long-chain alkyl radicals are commercially available and the amine oxides are therefore readily accessible (or likewise commercially available). Since these native fatty alkyl radicals often contain more or less large amounts of unsaturated portions, Formula 1 also includes the corresponding alkenylamine oxides in addition to the alkylamine oxides.

Bei den Zahlenwerten n und m 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 - Oxethylate.The numerical values n and m are generally average values, since technical oxyalkylation generally gives product mixtures. This also applies to the oxethylates listed here - for the sake of simplicity as uniformly formulated.

Diese Aminoxide werden in Präparationsmitteln für Synthesefasern wie etwa Polyester-, Polyamid-, Polyacrylnitril- oder-Polyolefinfasern eingesetzt. Solche Präparationsmittel bestehen üblicherweise aus 0-50 Gew.-% Ölen wie Esteröle oder Mineralöle, 0-60 Gew.-% Emulgator wie beispielsweise oxethylierte Fettalkohole, 0-60 Gew.-% eines Gleitmittels wie beispielsweise wasserlösliche endverschlossene Oxethylate, Ethylenoxid-Propylenoxid-Mischpolymerisate oder deren Ethern mit Fettalkoholen, 0-30 Gew.-% eines Antistatikums wie beispielsweise Ester aus P205 und Fettalkoholen oder oxethylierten Fettalkoholen sowie 1 bis 50, vorzugsweise 5-20 Gew.-%, eines oder mehrerer der oben beschriebenen Aminoxide.These amine oxides are used in preparation agents for synthetic fibers such as polyester, polyamide, polyacrylonitrile or polyolefin fibers. Preparations of this type usually consist of 0-50% by weight of oils such as ester oils or mineral oils, 0-60% by weight of emulsifier such as, for example, ethylated fatty alcohols, 0-60% by weight of a lubricant such as, for example, water-soluble end-capped oxyethylates, ethylene oxide-propylene oxide Copolymers or their ethers with fatty alcohols, 0-30% by weight of an antistatic such as, for example, esters of P 2 0 5 and fatty alcohols or ethoxylated fatty alcohols, and 1 to 50, preferably 5-20% by weight, of one or more of the amine oxides described above .

Die Aminoxide zeigen schon in verhältnismäßig geringer Dosierung eine hohe antistatische Wirkung. Die erforderlichen Einsatzmengen schwanken je nach Art und Menge der übrigen Komponenten (Öl, Emulgator) und lassen sich durch einfache Vorversuche leicht ermitteln. Üblicherweise werden 0,01 bis 2%, vorzugsweise 0,05 bis 1%, bezogen auf das Gewicht des Substrates, aufgebracht.The amine oxides show a high antistatic effect even in relatively low doses. The required quantities vary depending on the type and quantity of the other components (oil, emulsifier) and can be easily determined by simple preliminary tests. Usually 0.01 to 2%, preferably 0.05 to 1%, based on the weight of the substrate, is applied.

Hervorzuheben ist die geringe Flüchtigkeit dieser Verbindungen sowie eine deutlich verringerte Tendenz zur Verkohlung. Die gute Thermostabilität und die geringe Tendenz zur Verkohlung geht aus dem folgenden Test hervor, in dem jeweils 1 g einer der im folgenden beschriebenen Verbindungen auf 220°C erhitzt wurde. Dabei wurde die Flüchtigkeit in Prozent und die Vergilbung nach DIN 6162 gemessen.The low volatility of these compounds and a significantly reduced tendency to charring should be emphasized. The good thermal stability and the low tendency to charring are evident from the following test, in which 1 g of one of the compounds described below was heated to 220 ° C. The volatility in percent and the yellowing were measured in accordance with DIN 6162.

a) Erfindungsgemäße Produktea) Products according to the invention

Figure imgb0005
Figure imgb0005
Figure imgb0006
Figure imgb0006
Figure imgb0007
Figure imgb0007
Figure imgb0008
Figure imgb0008
Figure imgb0009
Figure imgb0009

b) Vergleich nach DE-PS 2 326 966b) Comparison according to DE-PS 2 326 966 1. Cocotdimethytaminoxid1. Cocot dimethytamine oxide

Figure imgb0010
Figure imgb0010
Figure imgb0011
Figure imgb0011

Ähnliche gute Effekte ergeben die Verbindungen

Figure imgb0012
Figure imgb0013
Figure imgb0014
Figure imgb0015
 The connections have similar good effects
Figure imgb0012
Figure imgb0013
Figure imgb0014
Figure imgb0015

In den folgenden Beispielen sind einige erfindungsgemäße Präparationsmittel in ihrer Zusammensetzung beschrieben, die ein Aminoxid der Formel 1 enthalten. Die Prozentangaben sind Gewichtsprozente.In the following examples, some preparation agents according to the invention are described in their composition, which contain an amine oxide of formula 1. The percentages are percentages by weight.

Beispiel 1example 1

  • 40% Butylstearat (Esteröl)40% butyl stearate (ester oil)
  • 50% Oleylalkohol . 5 Ethylenoxid (EO) (Emulgator)50% oleyl alcohol. 5 ethylene oxide (EO) (emulsifier)
  • 10% der Verbindung der Formel
    Figure imgb0016
         10% of the compound of the formula
    Figure imgb0016
Beispiel 2Example 2

  • 40% Cocosalkyl-O-(CH2CH2O)5CH3 (Gleitmittel)40% cocoalkyl-O- (CH 2 CH 2 O) 5 CH 3 (lubricant)
  • 30% Stearylalkohol . 8 EO (Emulgator)30% stearyl alcohol. 8 EO (emulsifier)
  • 5% Kaliumsalz des P2O5-Esters aus Laurylalkohol (Antistatikum)5% potassium salt of the P 2 O 5 ester from lauryl alcohol (antistatic)
  • 25% der Verbindung der Formel
    Figure imgb0017
         25% of the compound of the formula
    Figure imgb0017
Beispiel 3Example 3

  • 70% Mineralöl (Viskosität 100 mPaS bei 20° C)70% mineral oil (viscosity 100 mPaS at 20 ° C)
  • 25% i-C13H27-(EO)8H (Emulgator)25% iC 13 H 27 - (EO) 8 H (emulsifier)
  • 5% der Verbindung der Formel
    Figure imgb0018
         5% of the compound of the formula
    Figure imgb0018

Claims (3)

1. A preparation agent for synthetic fibers which contains an amine oxide of the formula 1
Figure imgb0021
in which R1 denotes C5-C22 alkyl or C5-C22 alkenyl, R2 denotes a group of the formula 2
Figure imgb0022
R3 denotes C, or C5-C22 alkyl, C5-C22 alkenyl or a group of the formula 2, either X denotes methyl and Y denotes hydrogen or X denotes hydrogen and Y denotes methyl, and n and m denote numbers form 1 to 8, it being necessary that the total of n and m does not exceed 10.
2. A preparation agent is claimed in claim 1, which contains an amine oxide of the formula 1 in which R1 and R2 denote C10-C16 alkyl or C10-C16 alkenyl.
3. Method of use of the preparation agent as claimed in claim 1 for the preparation of synthetic fibers.
EP81105655A 1980-07-24 1981-07-18 Oiling agent for synthetic fibres, and its use Expired EP0046507B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3028016 1980-07-24
DE19803028016 DE3028016A1 (en) 1980-07-24 1980-07-24 PREPARATION AGENTS FOR SYNTHESIS FIBERS AND THE USE THEREOF

Publications (2)

Publication Number Publication Date
EP0046507A1 EP0046507A1 (en) 1982-03-03
EP0046507B1 true EP0046507B1 (en) 1983-11-09

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EP81105655A Expired EP0046507B1 (en) 1980-07-24 1981-07-18 Oiling agent for synthetic fibres, and its use

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US (1) US4428846A (en)
EP (1) EP0046507B1 (en)
JP (1) JPS5751873A (en)
DE (2) DE3028016A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59116473A (en) * 1982-12-22 1984-07-05 竹本油脂株式会社 Oil agent for producing acrylic carbon fiber
DE29500807U1 (en) * 1995-01-19 1995-03-02 Föhl, Artur, 73614 Schorndorf Coupling between the belt shaft of a belt retractor and a belt tensioner rotary drive

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA721771A (en) * 1963-06-25 1965-11-16 Marchon Products Limited Surface-active agents and preparation and use thereof
US3554784A (en) 1967-06-05 1971-01-12 Procter & Gamble Softening of textile materials
FR2000142A1 (en) * 1968-01-11 1969-08-29 Armour Ind Chem Co
ES426477A1 (en) 1973-05-26 1976-07-01 Hoechst Ag Fiber-lubricating compositions
DE2927027A1 (en) 1979-07-04 1981-01-08 Hoechst Ag AGENT FOR LIQUID PARAFFINING YARN
DE2942156A1 (en) 1979-10-18 1981-04-30 Hoechst Ag, 6000 Frankfurt SLIMING AGENT

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DE3161371D1 (en) 1983-12-15
JPS5751873A (en) 1982-03-26
EP0046507A1 (en) 1982-03-03
DE3028016A1 (en) 1982-02-25
US4428846A (en) 1984-01-31

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