EP0562024A1 - Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique. - Google Patents

Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique.

Info

Publication number
EP0562024A1
EP0562024A1 EP92903258A EP92903258A EP0562024A1 EP 0562024 A1 EP0562024 A1 EP 0562024A1 EP 92903258 A EP92903258 A EP 92903258A EP 92903258 A EP92903258 A EP 92903258A EP 0562024 A1 EP0562024 A1 EP 0562024A1
Authority
EP
European Patent Office
Prior art keywords
maleic anhydride
polymer
alpha
substrate
olefin
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.)
Granted
Application number
EP92903258A
Other languages
German (de)
English (en)
Other versions
EP0562024B1 (fr
Inventor
Engelbert Pechhold
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to EP94203127A priority Critical patent/EP0648886B1/fr
Publication of EP0562024A1 publication Critical patent/EP0562024A1/fr
Application granted granted Critical
Publication of EP0562024B1 publication Critical patent/EP0562024B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • 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
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • 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
    • D06M15/244—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of halogenated hydrocarbons
    • D06M15/248—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of halogenated hydrocarbons containing chlorine
    • 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
    • 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
    • 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
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3562—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing nitrogen
    • 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
    • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
    • D06M15/3566—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing sulfur
    • 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/41—Phenol-aldehyde or phenol-ketone resins
    • D06M15/412—Phenol-aldehyde or phenol-ketone resins sulfonated
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/34—Polyamides
    • 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
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • 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
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

Definitions

  • the maleic anhydride polymers useful in the present invention can be prepared according to methods well-known in the art.
  • the maleic anhydride polymers thus obtained can be hydrolyzed to the free acid or their salts by reaction with water or alkali, or they can also be reacted with C1-4 alkyl alcohol to provide polymeric alpha-olefin/maleic acid monoesters, which have stainblocking properties.
  • the hydrolyzed maleic anhydride polymer, or the monoester polymer should be sufficiently water-soluble that uniform application to a fibrous polyamide surface can be achieved at an appropriate acidity.
  • applications using water dispersions of the polymer mixed with a suitable surfactant may be used to impart stain-resistance.
  • the olefin/maleic anhydride polymers of this invention can be used as such in treating polyamide textile substrates. They can be effectively applied to polyamide fibrous substrates by a wide variety of methods known to those skilled in the art, such as: padding, spraying, foaming in conjunction with foaming agents, batch exhaust in beck dyeing equipment, or continuous exhaust during a continuous dyeing operation. They can be applied by such methods to dyed or undyed polyamide textile substrates. In addition, they can be applied to such substrates in the absence or presence of a polyfluoroorgani ⁇ oil-, water-, and/or soil- repellent materials. In the alternative, such a polyfluoroorganic material can be applied to the textile substrate before or after application of the polymers of this invention thereto.
  • the maleic anhydride/propylene copolymer product in form of a dispersion, was discharged and filtered giving 46.7 g of a white powder having a number average molecular weight, by gel permeation chromatography (GPC) , of 2150.
  • GPC gel permeation chromatography
  • a portion of the solid copolymer (10 g) was hydrolyzed at 80-95°C in the presence of 82.5 g deionized water, 6.7 g 30 wt% sodium hydroxide and 2 drops of a 1% solution of benzyl- triethylammonium chloride resulting after about 1 to 2 hours in a clear solution containing 10 wt% of a water-soluble maleic anhydride/propylene copolymer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne un substrat fibreux en polyamide sur lequel est déposée une quantité d'une composition efficace pour conférer audit substrat une résistance aux taches, ladite composition comprenant un polymère soluble dans l'eau ou dispersible dans l'eau à base d'alpha-oléfine/d'anhydride maléique ou un mélange desdits polymères. L'invention concerne également des procédés de préparation desdits substrats. Le polymère d'anhydride maléique est utilisé soit sous sa forme hydrolysée soit sous sa forme résultant de sa réaction avec un alcool d'alkyle inférieur, de façon à produire un polymère d'alpha-oléfine/ester de monoalkyle d'acide maléique.
EP92903258A 1990-12-13 1991-12-13 Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique Expired - Lifetime EP0562024B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP94203127A EP0648886B1 (fr) 1990-12-13 1991-12-13 Agents antitâches contenant des polymères d'anhydride maléique/oléfine

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US62688590A 1990-12-13 1990-12-13
US626885 1990-12-13
PCT/US1991/009155 WO1992010605A1 (fr) 1990-12-13 1991-12-13 Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique

Related Child Applications (2)

Application Number Title Priority Date Filing Date
EP94203127A Division EP0648886B1 (fr) 1990-12-13 1991-12-13 Agents antitâches contenant des polymères d'anhydride maléique/oléfine
EP94203127.9 Division-Into 1994-10-27

Publications (2)

Publication Number Publication Date
EP0562024A1 true EP0562024A1 (fr) 1993-09-29
EP0562024B1 EP0562024B1 (fr) 1995-05-10

Family

ID=24512269

Family Applications (2)

Application Number Title Priority Date Filing Date
EP92903258A Expired - Lifetime EP0562024B1 (fr) 1990-12-13 1991-12-13 Agents anti-taches contenant des polymeres d'olefine/d'anhydride maleique
EP94203127A Expired - Lifetime EP0648886B1 (fr) 1990-12-13 1991-12-13 Agents antitâches contenant des polymères d'anhydride maléique/oléfine

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP94203127A Expired - Lifetime EP0648886B1 (fr) 1990-12-13 1991-12-13 Agents antitâches contenant des polymères d'anhydride maléique/oléfine

Country Status (9)

Country Link
EP (2) EP0562024B1 (fr)
JP (1) JPH06503386A (fr)
AU (1) AU660639B2 (fr)
CA (1) CA2098120A1 (fr)
DE (2) DE69109694T2 (fr)
IE (1) IE914340A1 (fr)
MX (1) MX9102558A (fr)
WO (1) WO1992010605A1 (fr)
ZA (1) ZA919847B (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX9301644A (es) * 1992-03-25 1993-09-01 Du Pont Substrato fibroso de poliamida, composicion y proceso para impartir resistencia a la decoloracion a tal substrato.
AU6026994A (en) * 1993-02-02 1994-08-29 E.I. Du Pont De Nemours And Company Durable hydrolized maleic anhydride polymer stain-resists
US5520962A (en) * 1995-02-13 1996-05-28 Shaw Industries, Inc. Method and composition for increasing repellency on carpet and carpet yarn
US5770656A (en) * 1995-09-22 1998-06-23 E.I. Du Pont De Nemours And Company Partial fluoroesters or thioesters of maleic acid polymers and their use as soil and stain resists
WO1997031149A1 (fr) * 1996-02-23 1997-08-28 E.I. Du Pont De Nemours And Company Agents antitaches a resine de resol/polymeres contenant de l'acide carboxylique
US6197378B1 (en) 1997-05-05 2001-03-06 3M Innovative Properties Company Treatment of fibrous substrates to impart repellency, stain resistance, and soil resistance
US6380336B1 (en) 1998-03-24 2002-04-30 Nano-Tex, Llc Copolymers and oil-and water-repellent compositions containing them
CA2324949A1 (fr) * 1998-03-24 1999-09-30 Avantgarb, Llc Tissu et autres matieres modifiees, procedes d'obtention
US6068805A (en) * 1999-01-11 2000-05-30 3M Innovative Properties Company Method for making a fiber containing a fluorochemical polymer melt additive and having a low melting, high solids spin finish
US6537662B1 (en) 1999-01-11 2003-03-25 3M Innovative Properties Company Soil-resistant spin finish compositions
US6207088B1 (en) 1999-01-11 2001-03-27 3M Innovative Properties Company Process of drawing fibers through the use of a spin finish composition having a hydrocarbon sufactant, a repellent fluorochemical, and a fluorochemical compatibilizer
US6120695A (en) * 1999-01-11 2000-09-19 3M Innovative Properties Company High solids, shelf-stable spin finish composition
US6117353A (en) * 1999-01-11 2000-09-12 3M Innovative Properties Company High solids spin finish composition comprising a hydrocarbon surfactant and a fluorochemical emulsion
US6077468A (en) 1999-01-11 2000-06-20 3M Innovative Properties Company Process of drawing fibers
CN100506927C (zh) 2005-03-21 2009-07-01 刘景春 多质离散效应纳米结构液膜及其制备方法和应用
US7579403B2 (en) 2006-04-04 2009-08-25 E. I. Du Pont De Nemours And Company Stain resist comprising hyperbranched maleic anhydride-diene polymers
US7579420B2 (en) 2006-04-04 2009-08-25 E. I. Du Pont De Nemours And Company Hyperbranched maleic anhydride-diene polymers
US7914890B2 (en) 2007-12-19 2011-03-29 E.I. Dupont De Nemours And Company Cyclic olefin-maleic acid copolymers for stain resists
US9353335B2 (en) 2013-11-11 2016-05-31 Ecolab Usa Inc. High alkaline warewash detergent with enhanced scale control and soil dispersion

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4623683A (en) * 1984-10-12 1986-11-18 S.C. Johnson & Son, Inc. Fabric finish with alpha olefin resins and process
US4871823A (en) * 1987-09-11 1989-10-03 S. C. Johnson & Son, Inc. 1-Alkene/excess maleic anhydride polymers
KR920006476B1 (ko) * 1987-12-21 1992-08-07 이 아이 듀우판 디 네모아 앤드 캄파니 방오성 폴리아미드 직물 지지체 및 직물 지지체에 방오성을 제공하는 방법
AU627711B2 (en) * 1988-03-11 1992-09-03 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9210605A1 *

Also Published As

Publication number Publication date
AU9157391A (en) 1992-07-08
DE69132592D1 (de) 2001-05-31
IE914340A1 (en) 1992-06-17
EP0648886A2 (fr) 1995-04-19
DE69109694D1 (de) 1995-06-14
EP0648886B1 (fr) 2001-04-25
MX9102558A (es) 1992-06-01
JPH06503386A (ja) 1994-04-14
WO1992010605A1 (fr) 1992-06-25
EP0562024B1 (fr) 1995-05-10
DE69132592T2 (de) 2001-10-18
CA2098120A1 (fr) 1992-06-14
EP0648886A3 (fr) 1996-05-15
ZA919847B (en) 1993-06-14
DE69109694T2 (de) 1996-01-11
AU660639B2 (en) 1995-07-06

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EP0564591B1 (fr) Matieres resistant aux taches a base de polymeres d'allylether ou de vinylether/d'anhydride maleique
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