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EP0502870B1 - Lubrifiants textiles renfermant des polymeres - Google Patents

Lubrifiants textiles renfermant des polymeres Download PDF

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Publication number
EP0502870B1
EP0502870B1 EP90916745A EP90916745A EP0502870B1 EP 0502870 B1 EP0502870 B1 EP 0502870B1 EP 90916745 A EP90916745 A EP 90916745A EP 90916745 A EP90916745 A EP 90916745A EP 0502870 B1 EP0502870 B1 EP 0502870B1
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EP
European Patent Office
Prior art keywords
weight
carbon atoms
monomers
alkyl
copolymers
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.)
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EP90916745A
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German (de)
English (en)
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EP0502870A1 (fr
Inventor
Ulrich Dr. Eicken
Andreas Dr. Botulinski
Heidi Fiedler
Manfred Gorzinski
Issac Fleming
Charles G. Dewitt
Jeffrey T. Langley
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Cognis IP Management GmbH
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Henkel AG and Co KGaA
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Priority claimed from DE3939549A external-priority patent/DE3939549A1/de
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0502870A1 publication Critical patent/EP0502870A1/fr
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Publication of EP0502870B1 publication Critical patent/EP0502870B1/fr
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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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof
    • D06M15/333—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof of vinyl acetate; Polyvinylalcohol
    • 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
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • 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
    • 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
    • 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
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
    • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • 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
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
    • 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
    • D06M13/402—Amides imides, sulfamic acids
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • D06M15/233—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated aromatic, e.g. styrene
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/31—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated nitriles
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/327—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated alcohols or esters thereof
    • 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 relates to textile lubricants which contain certain acrylate and / or methacrylate-containing homopolymers and / or copolymers, a process for producing textile lubricants containing these homopolymers and / or copolymers and the use of these homopolymers and / or copolymers in textiles Lubricants to reduce the spin-off of textile lubricants from the fiber surface during fiber manufacture and / or processing.
  • EP-A-261 415 and EP-A-127 293 it is known from European property rights EP-A-261 415 and EP-A-127 293 that the use of high molecular weight polyisobutenes and the use of copolymers which use butenes as monomer components in combination with C 5 - 2o -a-0! efinen contain, reduce the splashing of winding oils during yarn processing.
  • the requirements for the polymeric viscosity index improvers are primarily specified on the basis of the molecular weight, for example polyisobutenes with molecular weights between 20,000 and 2,000,000, polyalkylstyrenes with molecular weights between 20,000 and 2,000,000 or polymethacrylates with molecular weights between 300,000 and 800 000.
  • DE-A-21 29 958 describes a process for producing a multifilament synthetic texturing yarn.
  • the cohesion of the individual fibers is determined by e.g. improved by polyvinyl copolymers which are applied via an impregnation bath.
  • the impregnation baths contain approx. 10% by weight of polyvinyl copolymers.
  • GB-A-758 479 describes partially water-soluble, neutralized copolymers of acrylic acid and its alkyl esters as textile sizing agents. To achieve the desired effect, 10 to 20% by weight of polymer must be used. The sizing agents do not contain any water-insoluble smoothing agents.
  • French patent FR-A-15 54 241 describes emulsions which serve to inhibit corrosion and contain aliphatic amines, acetic acid, an emulsifier and a homo- and / or copolymer of (meth) acrylic esters with free acid or salt groups.
  • French application FR-A-20 86 310 describes spin finishes which contain polymers with aromatic sulfo groups or polymers made from maleic anhydride or copolymers made from maleic anhydride with ethylene, butylene or other olefins.
  • the degrees of polymerization are in the range of 3 to 10, i.e. but that the intrinsic viscosities of over 200 ml / g are never reached.
  • GB-A-12 46 134 teaches that the processability of textile fibers is improved by fiber preparations consisting of mixtures of copolymers of siloxanes and alkylene glycols with phosphoric acid partial esters. In particular, the tendency towards electrostatic charging is reduced. It cannot be inferred from this that these copolymers together with polymers based on polyacrylates with intrinsic viscosities of over 200 ml / g prevent the fiber preparation from being thrown off.
  • the intrinsic viscosity is determined according to the method described in B. Vollmert: "Floor plan of macromolecular chemistry", Volume 111, page 55 ff, E. Vollmert Verlag, Düsseldorf 1988. For copolymers containing more than 5% by weight of ionic groups, the viscosity increases proportionally with the concentration at high concentrations, while the viscosity decreases with increasing concentration at low concentrations.
  • the intrinsic viscosities of these copolymers are determined with the aid of diagrams in which the concentration is plotted on the abscissa and the viscosity is plotted on the ordinate by extrapolation of the part which rises linearly at high concentrations to the concentration 0.
  • the content of monomers from group B is preferably at most 60% by weight, based on the total amount of monomers.
  • homopolymers and / or copolymers with intrinsic viscosities contain one or more monomers from group A.
  • monomers from group A acrylic acid and / or methacrylic acid alkyl esters with 1 to 18 carbon atoms in the linear, branched-chain and / or cyclic, monovalent alkyl alcohol radicals are preferred and acrylic acid and / or methacrylic acid alkyl esters with 1 to 12 carbon atoms in the linear, branched-chain and / or cyclic, monovalent alkyl alcohol radicals, for example ethyl acrylate, n-butyl methacrylate , n-butyl acrylate, i-butyl methacrylate, n-hexyl methacrylate, ethylhexyl acrylate and / or ethylhexyl methacryl
  • Copolymers can be built up from monomeric acrylic acid and / or methacrylic acid alkyl esters alone or in combination with one or more monomers from group B.
  • Unsaturated aliphatic carboxylic acids with 3 to 5 carbon atoms for example acrylic acid, methacrylic acid and / or itaconic acid, are preferably used as group B monomers with group A monomers.
  • Homopolymers and / or copolymers with intrinsic viscosities, measured in tetrahydrofuran at 20 ° C, of at least 400 ml / g and particularly preferably those with intrinsic viscosities, measured in tetrahydrofuran at 20 ° C, of at least 600 ml / g in textile lubricants are preferably used .
  • the homo- and / or copolymers to be used according to the invention can be prepared in a manner known per se by emulsion polymerization in an inert gas atmosphere by adding the monomer or the monomer mixture to water which contains anionic surfactants and then adding the catalyst required for the polymerization.
  • the polymerization temperatures are at most 60 ° C., polymerization temperatures in the range from 25 to 35 ° C. being preferred in particular during the reaction period, which is characterized by an exothermic course of the reaction. To complete the polymerization reaction, it may be appropriate to raise the reaction temperature to a maximum of 60 ° C.
  • Anionic surfactants which are suitable for use in the emulsion polymerizations are alkali and / or ammonium salts of C 8-22 alkyl sulfonates, aryl sulfonates and / or alkyl aryl sulfonates with 1 to 10 C atoms in the alkyl radicals and / or alkali and / or ammonium salts of C 8-22 alkyl sulfates and / or C 8-22 alkyl ether sulfates such as sodium lauryl sulfate and / or C 12/14 fatty alcohol sulfate • 10 moles of ethylene oxide (EO), sodium salt, and / or alkali metal and / or ammonium salts of Alkylphenolsulfaten and / or alkylphenol ether sulfates with 1 up to 10 carbon atoms in the alkyl radicals, for example i-nonylphenol 4 mol of EO sulfate,
  • Alkali metal salts of sulfosuccinic acid derivatives are preferably used, which, according to known processes, are converted by reacting maleic anhydride 1. with straight-chain, branched-chain or cyclic, optionally alkoxylated Cs-22-alkyl alcohols or with optionally alkoxylated alkylphenols or with straight-chain, branched-chain or cyclic, optionally alkoxylated Ca- 22 - Alkylamines and 2. are accessible with alkali hydrogen sulfites or alkali sulfites. Examples are the sodium salts of diethylhexylsulfosuccinate, C 12/14 fatty alcohol.
  • Anionic surfactants are used in amounts between 1 and 15% by weight, preferably in amounts between 3 and 10% by weight, in each case based on the total monomer mixture.
  • the catalysts (initiator systems) for the emulsion polymerizations which can be used are in particular the redox systems known from European application EP-A-0 48 084, for example ammonium persulfate in combination with ascorbic acid or ammonium persulfate or potassium persulfate in combination with sodium dithionite, sodium sulfite or sodium thiosulfate.
  • the initiator systems are used in amounts of 0.05 to 0.8% by weight, preferably in amounts of 0.1 to 0.5% by weight, in each case based on the total monomer weight.
  • aqueous dispersions which contain 5 to 40% by weight of the homo- and / or copolymers to be used according to the invention with intrinsic viscosities of at least 200 ml / g.
  • Textile lubricants contain homo- and / or copolymers in amounts of at most 2% by weight of active substance.
  • textile lubricant includes in particular spin finishes for continuous filaments, primary spin finishes for staple fibers and lubricants for further processing, for example winding oils and / or twist oils.
  • the textile lubricants according to the invention can be used as smoothing agents, for example mineral oils, carboxylic acid esters, made from aliphatic carboxylic acids with 8 to 22 carbon atoms and straight and / or branched, optionally alkoxylated alkyl alcohols with 1 to 22 carbon atoms, for example isobutyl stearate, n-hexyl laurate, methyl palmitate , Tallow fatty acid 2-ethylhexyl ester, coconut fatty acid triglycerides and / or trimethylolpropane tripelargonate, and / or polyalkylene glycols, for example ethylene oxide / propylene oxide mixed polymers with average molecular weights between 600 and 6,000 and / or silicones.
  • mineral oils for example mineral oils, carboxylic acid esters, made from aliphatic carboxylic acids with 8 to 22 carbon atoms and straight and / or branched, optionally alkoxylated alkyl alcohols
  • the silicone component is to be used as a smoothing agent in the textile lubricants, it should be present in at least 0.02% by weight, preferably at least 0.05% by weight and in particular at least 0.09% by weight on lubricants - be included.
  • Suitable emulsifiers, wetting agents and / or antistatic agents are anionic, cationic and / or nonionic surfactants, such as mono- and / or diglycerides, for example glycerol mono- and / or glycerol dioleate, alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols 8 to 24 C-atoms and / or C 8-18 alkyl phenols, for example castor oil ethoxylated with 10 to 40 moles of ethylene oxide (EO) and / or C, 6 - 18 fatty alcohols, alkoxylated with ethylene oxide and / or propylene, if desired, alkoxylated C 8-24 fatty acid mono- and / or diethanolamides, for example optionally ethoxylated oleic acid and / or - diethanolamide, tallow fatty acid monoethanolamide and / or diethanolamide and / or Koco
  • the textile lubricants according to the invention can be used as additives thread-closing agents, for example fatty acid sarcosides and / or copolymers with maleic anhydride and / or polyurethanes according to DE-A-38 30 468, pH regulators, for example aliphatic Ci- 22 carboxylic acids and / or Cl-4- Hydroxycarboxylic acids, such as acetic acid, glycolic acid and / or oleic acid, alkali metal hydroxides, such as potassium hydroxide and / or amines, such as triethanolamine, bactericides and / or corrosion inhibitors.
  • thread-closing agents for example fatty acid sarcosides and / or copolymers with maleic anhydride and / or polyurethanes according to DE-A-38 30 468
  • pH regulators for example aliphatic Ci- 22 carboxylic acids and / or Cl-4- Hydroxycarboxylic acids, such as acetic acid, glycolic
  • a sufficient amount of an amine component consisting essentially of one or more amines with HLB values of not more than 8, preferably not more than 5.7, should be present in the lubricant be contained in order to avoid undesirable clouding or precipitation of solids.
  • the amount of amine component added is preferably at least 0.5% by weight, preferably at least 1% by weight and in particular at least 2.8% by weight, based on the lubricant.
  • a particularly preferred amine mixture can be prepared by condensing tallow amines with an average of 2 moles of ethylene oxide to 1 mole and is referred to below as "TAM-2".
  • TAM-2 tallow amines with an average of 2 moles of ethylene oxide to 1 mole
  • the amine component per se can replace alkali hydroxides as pH regulation with corrosion-inhibiting and certain antistatic properties, it is often advantageous to use both components if the silicones described above are present.
  • the total amount of substances present, including the amines and any alkali metal hydroxides present, should together be sufficient to neutralize any acidic substances, such as carboxylic acids, present in the entire lubricant composition.
  • Another common and often preferred optional ingredient is a partially esterified phosphoric acid, such as the mono- and / or dioctyl ester of phosphoric acid. If such partially esterified phosphoric acid (s) are incorporated, their amount is at least 0.5% by weight, preferably 1% by weight, based on the lubricant.
  • Water-soluble and / or water-dispersible smoothing agents, emulsifiers, antistatic agents, wetting agents and / or additives can be used in any mixing ratio to one another in the textile lubricants according to the invention. Usually, however, the content of additives in textile lubricants is not above 10% by weight.
  • acrylate and / or methacrylate-containing homopolymers and / or copolymers with intrinsic viscosities, measured in tetrahydrofuran at 20 ° C., of at least 200 ml / g, which are in the form of aqueous dispersions, into textile lubricants is carried out according to the invention in such a way that that the polymer dispersions are added to textile lubricants with stirring at temperatures between 15 and 80 ° C under normal pressure. Even while the polymers are being added, they are distributed homogeneously in the lubricants. In order to accelerate the dissolution of the polymer particles, it may be expedient to heat the lubricants to 40 to 100 ° C., if desired without stirring. If desired, the water content of the lubricants according to the invention obtained can be reduced by distillation.
  • spin finishes and lubricants for further processing for example winding oils which contain, as polymer compounds, acrylate and / or methacrylate-containing homopolymers and / or copolymers with intrinsic viscosities, measured in tetrahydrofuran at 20 ° C, of at least 200 ml / g, takes place in known way, for example with the help of preparation rollers or metering pumps.
  • the application amount of spin finishes or lubricants for further processing in undiluted form or in the form of aqueous emulsions is between 0.05 and 5% by weight of active substance, based on the weight of the fiber material.
  • Fiber materials made of, for example, polyester, polyamide, polypropylene and / or polyacrylic can be treated with the textile lubricants according to the invention.
  • the textile lubricants according to the invention are liquid and show thread formation when a glass rod immersed in undiluted textile lubricants is pulled out again at 20 ° C.
  • the adhesion to the fiber surface and thus the spray behavior when textile lubricants according to the invention are used are significantly improved in fiber production and / or processing.
  • Homo- and / or copolymers containing acrylate and / or methacrylate with intrinsic viscosities, measured in tetrahydrofuran at 20 ° C, of at least 200 ml / g, can be easily incorporated into textile lubricants.
  • the polymers to be used according to the invention have the advantage that they are also soluble in the lubricants containing carboxylic acid esters, which are to be preferred for environmental reasons.
  • the aqueous, ammonium persulfate-containing solution and then the aqueous, ascorbic acid-containing solution was first added dropwise. During the approximately 2-hour, exothermic polymerization reaction, a temperature of 35 ° C. was not exceeded. After 2 hours, 0.05 g of ammonium persulfate, dissolved in 3 ml of water and 0.075 g of ascorbic acid, dissolved in 3 ml of water, were added in succession and the polymerization was continued at 60 ° C. for one hour. 20% by weight, coagulate-free emulsions were obtained.
  • Table 1 shows the monomers used and the intrinsic viscosities of the homo- and copolymers 1.1 to 1.9 obtained.
  • aqueous ascorbic acid-containing solution was added dropwise to the monomeric, persulfate-containing, aqueous mixture, which had been heated to about 29 ° C. A temperature of 30 ° C. was not exceeded during the approximately 1-hour, exothermic polymerization reaction. The polymerization was then continued for 1 hour at 60 ° C. with stirring. 20% by weight, coagulate-free emulsions were obtained.
  • Table 1 shows the monomers used and the intrinsic viscosities of the copolymers 2.1-2.3 obtained.
  • a textile lubricant consisting of 78.5% by weight of i-butyl stearate, 5% by weight of oleyl / cetyl alcohol • 5 mol of EO, 2.2% by weight of coconut fatty acid monoethanolamide • 4 mol of EO, 0.8% by weight .-% oleic acid, 6% by weight secondary fatty alcohol 3 mol EO (Tergitol R 15S3, manufacturer: Union Carbide), 6% by weight secondary fatty alcohol 7 mol EO (Tergitol R 1557, manufacturer: Union Carbide) and 1.5 % By weight of water was added with stirring (maximum stirring speed of a head stirrer with propeller stirrer) at 20 ° C.
  • Example 1b the polymer emulsion prepared according to Example 1b. After 30 seconds the polymer emulsion had spread evenly and a clear solution had formed. The stirring speed was then reduced as much as possible and the textile lubricant was heated to 60 ° C. to accelerate the dissolution of the polymer particles.
  • the lubricant obtained was applied as a rinsing oil to a textured polyester yarn in an amount of 1.5% by weight.
  • the sprayed-off amount was collected and weighed. Compared to the lubricant without polymer additive, the amount of polymer-containing lubricant sprayed was reduced by 82%.
  • a polymer-containing lubricant was made from 995 g of a lubricant consisting of 85% by weight n-hexyl laurate, 6% by weight mono / diphosphate mixture of lauryl alcohol, 6 mol EO, monoethanolamine salt, 4% by weight secondary fatty alcohol, 3 mol EO and 5% by weight of secondary fatty alcohol 7 mol EO, and 5 g of a polymer emulsion prepared according to Example 1 c.
  • the lubricant obtained was applied as a rinsing oil on a polyamide yarn in a circulation of 1% by weight during the rewinding.
  • the sprayed-off amount was collected and weighed. Compared to the lubricant without the addition of polymer, a 94% reduction in the sprayed amount was achieved with the polymer-containing lubricant.
  • a polymer-containing lubricant was made from 995 g of a lubricant consisting of 55% by weight trimethylolpropane tripelargonate, 10% by weight arylsulfonate, sodium salt, 6% by weight oleic acid, 2% by weight triethanolamine, 15% by weight.
  • Oleyl / cetyl alcohol • 5 moles of EO, 6% by weight of 5 castor oil • 30 moles of EO and 6% by weight of water, and 5 g of a polymer emulsion prepared according to Example 1 g.
  • a polymer-containing lubricant was made from 995 g of a lubricant consisting of 60% by weight of i-butyl stearate, 10% by weight of oleic acid, 8% by weight of mono / diphosphate mixture of lauryl alcohol, 5% by weight of secondary fatty alcohol 9 Mol EO (Tergitol R 15S9, manufacturer: Union Carbide), 4 wt .-% sodium dioctyl sulfosuccinate, 6 wt .-% oleyl / cetyl alcohol • 5 mol EO and 7 wt .-% of a 47 wt .-% potassium hydroxide solution, and 5 g a polymer emulsion prepared according to Example 1 h.
  • a lubricant consisting of 60% by weight of i-butyl stearate, 10% by weight of oleic acid, 8% by weight of mono / diphosphate mixture of lauryl alcohol, 5% by weight of
  • a 15% by weight aqueous emulsion was prepared from the polymer-containing lubricant by stirring 150 g of this lubricant in 850 g of water.
  • the emulsion obtained was applied to a polyester yarn in an overlay of 1.5% by weight immediately after spinning.
  • the sprayed-off amount was collected and weighed. In comparison to the lubricant without the addition of polymer, the amount of sprayed off was reduced by 38% with the polymer-containing lubricant.
  • the base lubricant consisted entirely of liquid oligomers of 1-decene.
  • a sample of the base lubricant was mixed with about 10% by weight of 2-propanol and 1% by weight of the emulsion prepared according to Example 1.9 above. The mixture was then heated sufficiently to remove substantially all of the 2-propanol and water (from the emulsion). The mixture was then completely clear and suitable for use as a spin-resistant textile lubricant with excellent lubricating properties.
  • Aqueous phosphoric acid was added to the emulsion prepared according to Example 1.9, which corresponded to 1% by weight of the base lubricant, and the mixture was allowed to stand for 24 hours. The mixture was then completely clear and suitable for use as a spin-resistant textile lubricant with excellent lubricating properties.
  • Example L Analogously to Example L, but with the difference that technical isobutyl stearate was used instead of the mixture of the methyl esters, a clear, high-quality, spin-resistant lubricant was obtained which did not require any addition, such as the water used in Example L.
  • Example M Analogously to Example M, but with the difference that mixed esters of C 8-10 alcohols with Cs-io fatty acids replaced the isobutyl stearate, a lubricant of the same quality as in Example M was obtained.
  • Example L Analogously to Example L, but with the difference that a liquid mixture of oligomers of 1-decene was used instead of the mixture of methyl esters, a clear, high-quality, spin-resistant lubricant was obtained which did not require any addition, such as the water used in Example L. .
  • Example 1.9 To a textile base lubricant consisting of pelargonic acid esters of methanol 300 mol EO, an amount of the emulsion prepared according to Example 1.9, which corresponded to 1% by weight of the base lubricant, was added and the mixture was left to stand for 24 hours. The mixture was then slightly cloudy, but remained homogeneous and was suitable for use as a spin-resistant textile lubricant with an excellent lubricating effect.
  • Example 1.9 To a textile base lubricant consisting of technical lauric acid 9 mol EO, an amount of the emulsion prepared according to Example 1.9, which corresponded to 1% by weight of the base lubricant, was added and the mixture was left to stand for 24 hours. The mixture was then slightly cloudy, but remained homogeneous and was suitable for use as a spin-resistant textile lubricant with an excellent lubricating effect.

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  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Abstract

L'invention concerne des lubrifiants textiles renfermant des homo- et/ou copolymères déterminés, à base d'acrylate et/ou de méthacrylate, un procédé de fabrication de tels lubrifiants textiles, ainsi que l'application de ces homo- et/ou copolymères dans des lubrifiants textiles, en vue de réduire les projections de ces lubrifiants à partir de la surface des fibres, au cours de la fabrication et/ou du traitement de ces fibres.

Claims (12)

1. Agents lubrifiants à base d'agents de lissage, d'agents émulsionnants, d'agents antistatiques et/ou d'agents mouillants, ayant une teneur en composés polymères caractérisés en ce que ceux-ci contiennent :
30 à 97 % d'agent de lissage insolubles dans l'eau,
0,001 à 2 % en poids d'homo- et/ou de copolymères renfermant des esters d'alcoyle d'acide acrylique et/ou d'acide méthacrylique avec des viscosités limites mesurées dans le tétrahydrofuranne à 20 ° C, d'au moins 200 ml/g et qui renferment comme monomères :
A. de 100 à 30 % en poids d'ester d'alcoyle d'acide acrylique et/ou d'acide méthacrylique ayant de 1 à 22 atomes de carbone dans les radicaux d'alcoylalcool monovalents et,
B. de 0 à 70 % en poids de monomères choisis dans un ou plusieurs des groupes suivants :
- acides carboxyliques aliphatiques, non saturés ayant de 3 à 5 atomes de carbone et/ou leurs amides.
- styrène et/ou des alcoylstyrènes ayant de 1 à 4 atomes de carbone dans les radicaux alcoyle, nitrile crylique, un ester de vinyle d'acide carboxylique aliphatique en Ci à C18 et/ou des esters alcoylés d'acide acrylique et/ou d'acide méthacrylique contenant des groupes amines ayant de 2 à 6 atomes de carbone dans les radicaux alcoyle,
0,5 à 69,997 % en poids d'agents de lissage solubles dans l'eau et/ou dispersibles dans l'eau, des agents émulsionnants, des agents antistatiques, des agents mouillants, et/ou des additifs, par exemple des régulateurs de valeur de pH, des agents de terminaison du fil, des bactéricides et/ou des agents de protection contre la corrosion et,
0,0015 à 67 % en poids d'eau.
2. Agents lubrifiants pour textiles selon la revendication 1, caractérisés en ce que les homo- et/ou les copolymères renferment en tant que monomères, de 100 à 40 % en poids de monomères choisis dans le groupe A et de 0 à 60 % en poids de monomères choisis dans le groupe B.
3. Agents lubrifiants pour textile selon l'une ou les deux revendications 1 à 2, caractérisés en ce que les homo- et/ou copolymères renferment en tant que monomères A des esters d'alcoyle d'acide acrylique et/ou méthacrylique ayant de 1 à 18 atomes de carbone, de préférence de 1 à 12 atomes de carbone dans les radicaux alcoylalcool monovalents.
4. Agents lubrifiants pour textile selon l'une ou plusieurs des revendications 1 à 3, caractérisés en ce que les copolymères renferment comme monomères B des acides carboxyliques aliphatiques non saturés avec 3 à 5 atomes de C.
5. Agents lubrifiants pour textiles selon l'une ou plusieurs des revendications 1 à 4, caractérisés en ce que les homo- et/ou copolymères possèdent des viscosités limites mesurées dans le tétrahydrofuranne à 20°C, d'au moins 400 ml/g, de préférence d'au moins 600 ml/g.
6. Agents lubrifiants textiles selon l'une des revendications 1 à 5, caractérisés en ce que l'on utilise des agents lubrifiants textiles qui renferment comme agents de lissage :
1- Au moins 0,02 % en poids d'un composant siliconé ayant une viscosité à température ambiante, de 5 à 70 mm"/s (cSt) dans lesquels ce composant siliconé est constitué essentiellement de molécules ayant les structures moléculaires qui correspondent à la formule générale chimique :
Figure imgb0007
dans laquelle R1, R2, R3, R4 et R5 peuvent être identiques ou différents, et signifient un radical alcoyle univalent ayant de 1 à 18 atomes de carbone, et
m est un nombre entier positif,
p est 2 ou 3
n, q et r respectivement indépendamment l'un de l'autre sont égaux à zéro ou à un nombre positif entier et chacun des blocs de molécules désignés par les références inférieures, le cas échéant avec différentes valeurs pour les références inférieures peut être répété dans la structure effective de chaque polymère, blocs parmi lesquels ceux avec les références m et n le cas échéant sont mélangés dans la chaîne de squelette du polymère l'un avec l'autre d'une manière statistique et ceux avec les références q et r sont mélangés le cas échéant d'une manière statistique l'un avec l'autre dans une ou plusieurs chaînes latérales de polyéthers quelconques, qui peuvent se présenter dans une molécule individuelle de polymère à l'intérieur des composants.
7. Procédé d'obtention d'agent lubrifiant de textiles à base d'agents de lissage, d'agents émulsionnants, d'agents antistatiques, et/ou d'agents mouillants ayant une teneur en composés polymères, caractérisé en ce que les homo- et/ou copolymères à mettre en oeuvre comme composés polymères qui possèdent des viscosités limites mesurées dans le tétrahydrofuranne à 20 ° C, d'au moins 200 ml/g et qui contiennent comme monomères :
A. de 100 à 30 % en poids d'ester d'alcoyle d'acide acrylique et/ou méthacrylique avec de 1 à 22 atomes de carbone dans les radicaux alcoylalcool univalents et
B. de 0 à 70 % en poids de monomères choisis dans un ou plusieurs des groupes suivants :
- acides carboxyliques aliphatiques non saturés ayant de 3 à 5 atomes de carbone et/ou leurs amides,
- styrène et/ou alcoylstyrènes avec de 1 à 4 atomes de carbone dans les radicaux alcoyle,
- nitrile acrylique
- ester de vinyle d'acide carboxylique aliphatique en Ci à C18 et/ou
- esters d'alcoyle d'acide acrylique et/ou méthacrylique ayant de 2 à 6 atomes de carbone dans les radicaux alcoyle, contenant des groupes aminés

sont ajoutés en quantités allant de 0,001 à 2 % en poids, sous forme de dispersions dans l'eau d'agent lubrifiant pour textiles sous agitation à des températures comprises entre 15 et 80 °C sous pression normale.
8. Utilisation d'homo- et/ou de copolymères qui possèdent une viscosité limite mesurée dans le tétrahydrofuranne à 20 ° C, d'au moins 200 ml/g et qui renferment comme monomères.
A. de 100 à 30 % en poids d'esters d'alcoyle d'acide acrylique et/ou d'acide méthacrylique ayant de 1 à 22 atomes de carbone dans les radicaux alcoylalcool univalents, et
B. de 0 à 70 % en poids des monomères choisis dans l'un ou plusieurs des groupes suivants :
- acides carboxyliques aliphatiques non saturés ayant de 3 à 5 atomes de carbone et/ou leurs amides
- styrène et/ou alcoylstyrènes ayant de 1 à 4 atomes de carbone dans les radicaux alcoyle.
- nitrile acrylique
- esters de vinyle d'acide carboxylique en Ci à C18 aliphatiques et/ou
- esters d'alcoyle d'acide acrylique et/ou méthacrylique renfermant des groupes amine, ayant de 2 à 6 atomes de carbone dans les radicaux alcoylalcool,

dans des agents lubrifiants de textiles en quantités allant de 0,001 à 2 % en poids en vue de la diminution de l'essorage des agents lubrifiants de textiles de la surface des fibres pendant la production et/ou le façonnage des fibres.
9. Utilisation selon la revendication 8, caractérisée en ce que l'on utilise des homo- et/ou copolymères qui renferment comme monomères de 100 à 40 % en poids de monomères du groupe A et de 0 à 60 % en poids de monomères du groupe B.
10. Utilisation selon l'une des deux revendications 8 à 9, caractérisée en ce que l'on utilise des homo- et/ou copolymères qui renferment comme monomères A un ester d'alcoyle d'acide acrylique et/ou d'acide méthacrylique ayant de 1 à 18 atomes de carbone, de préférence de 1 à 12 atomes de carbone dans les radicaux alcoylalcool univalents.
11. Utilisation selon l'une ou plusieurs des revendications 8 à 10, caractérisée en ce que l'on utilise des copolymères qui renferment comme monomère B des acides carboxyliques aliphatiques non saturés ayant de 3 à 5 atomes de carbone.
12. Utilisation selon l'une ou plusieurs des revendications 8 à 11, caractérisée en ce que l'on utilise des homo- et/ou des copolymères ayant des viscosités limites mesurées dans le tétrahydrofuranne à 20 ° C, d'au moins 400 ml/g, de préférence d'au moins 600 ml/g.
EP90916745A 1989-11-30 1990-11-22 Lubrifiants textiles renfermant des polymeres Expired - Lifetime EP0502870B1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE3939549 1989-11-30
DE3939549A DE3939549A1 (de) 1989-11-30 1989-11-30 Polymerhaltige textile gleitmittel
US58135890A 1990-09-12 1990-09-12
PCT/EP1990/001989 WO1991008336A1 (fr) 1989-11-30 1990-11-22 Lubrifiants textiles renfermant des polymeres
US581358 1995-12-29

Publications (2)

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EP0502870A1 EP0502870A1 (fr) 1992-09-16
EP0502870B1 true EP0502870B1 (fr) 1994-10-19

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JP (1) JPH05502273A (fr)
KR (1) KR0155538B1 (fr)
DE (1) DE59007527D1 (fr)
ES (1) ES2063379T3 (fr)
WO (1) WO1991008336A1 (fr)

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DE4201978A1 (de) * 1991-05-29 1992-12-03 Henkel Kgaa Fettsaeuremethylester in schmaelzmitteln fuer streichgarnspinnerei

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Publication number Priority date Publication date Assignee Title
GB758479A (en) * 1954-02-12 1956-10-03 Ici Ltd Textile sizes
US2845689A (en) * 1954-07-06 1958-08-05 American Cyanamid Co Warp size containing dicyandiamide and a polyacrylate salt
US3444090A (en) * 1967-03-01 1969-05-13 Grace W R & Co Stabilizing filming amine emulsions
GB1246134A (en) * 1968-04-22 1971-09-15 Du Pont Process for improving the performance of synthetic filaments in textile operations by application of a textile treating composition
JPS4841798B1 (fr) * 1970-04-24 1973-12-08
GB1362841A (en) * 1970-06-16 1974-08-07 Kanebo Ltd Process of manufacturing a thermoplastic synthetic multifilament textured yarn

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JPH05502273A (ja) 1993-04-22
KR927003913A (ko) 1992-12-18
EP0502870A1 (fr) 1992-09-16
ES2063379T3 (es) 1995-01-01
DE59007527D1 (de) 1994-11-24
KR0155538B1 (ko) 1998-12-01
WO1991008336A1 (fr) 1991-06-13

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