WO2003093567A1 - Appret hydrophile pour supports fibreux - Google Patents

Appret hydrophile pour supports fibreux Download PDF

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Publication number
WO2003093567A1
WO2003093567A1 PCT/US2002/013783 US0213783W WO03093567A1 WO 2003093567 A1 WO2003093567 A1 WO 2003093567A1 US 0213783 W US0213783 W US 0213783W WO 03093567 A1 WO03093567 A1 WO 03093567A1
Authority
WO
WIPO (PCT)
Prior art keywords
carboxyl
acid
fibrous substrate
contain
containing polymer
Prior art date
Application number
PCT/US2002/013783
Other languages
English (en)
Inventor
David S. Soane
Dan B. Millward
Matthew R. Linford
Ryan Lau
Eric G. Green
William Ware, Jr.
Original Assignee
Nano-Tex, Llc
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 Nano-Tex, Llc filed Critical Nano-Tex, Llc
Priority to AU2002367913A priority Critical patent/AU2002367913A1/en
Priority to PCT/US2002/013783 priority patent/WO2003093567A1/fr
Publication of WO2003093567A1 publication Critical patent/WO2003093567A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • 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
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives 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
    • 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
    • D06M2101/32—Polyesters
    • 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

Definitions

  • FIELD OF THE INVENTION This invention is directed to the field of fabric finishes, and more particularly to polymeric fabric finishes that impart hydrophilicity and other properties to fibers, yarns, textiles, or other fibrous substrates.
  • Synthetic textile materials such as nylon and polyester, are uncomfortable to wear due to their poor permeability to water. In hot weather, sweat cannot easily penetrate (or wick) through these fabrics and evaporate. The poor wicking and permeability are due to the natural hydrophobicity of nylon and polyester polymers; water does not readily spread out over surfaces composed of these materials. Nylon and polyester also often exhibit static cling and stain retention due to their hydrophobicity.
  • a method for imparting durable hydrophilic properties to nylon, polyester, and other synthetic materials would thus be desirable. This may be achieved by attaching hydrophilic materials to the hydrophobic fibers. Imparting hydrophilic properties to the hydrophobic substrate will also diminish or eliminate static cling and enable the release of stains during laundering.
  • U.S. Patent 3,377,249 to Marco discloses the application of a stain-releasing finish to fabrics made of polyester, cotton, and polyester/cotton blends.
  • the formulations comprise an acrylate copolymer (composed of at least 20% acrylic acid monomer) emulsion, an aminoplast resin, and a resin catalyst.
  • the fabrics thus treated show stain-releasing properties durable to between five and ten home launderings.
  • the carboxylates of the PAA are activated by reaction with EDC; some of the activated carboxylates then react with amine groups on the chain ends of the nylon polymers while the rest are hydrolyzed back to carboxylate form.
  • the NHS is believed to aid in slowing the rate of hydrolysis. After incubating the film in the solutions for times ranging from 0.5 to 18 hours, and at temperatures ranging from 0 to 60 °C, the treated films were removed and rinsed at least six times with deionized water. The authors report that a drop of water placed on untreated nylon 6,6 film spreads slowly over the surface, whereas a drop placed on a treated film immediately spreads to cover the surface. Disadvantages to this method are that large amounts of the expensive reagents EDC and NHS, in greater-than-stoichiometric amounts relative to the number of carboxyl groups, are required for grafting.
  • the invention of a treatment for polyester, nylon, and other synthetic, hydrophobic materials that renders the treated material hydrophilic.
  • the treatment durably attaches hydrophilic material directly to a hydrophobic substrate, rendering the substrate hydrophilic without altering the other properties of the material.
  • This invention is directed to fabric finishes or treatment preparations for nylon, polyester, and other hydrophobic textile materials that will render them hydrophilic.
  • the finishes of the invention are comprised primarily of polymers that contain carboxyl groups, salts of carboxyl groups, or moieties that can be converted to carboxyl groups by a chemical reaction (referred to herein as "carboxyl precursors") as well as at least one cross-linking agent.
  • Fibrous substrates such as textiles or webs, are exposed to these treatment preparations, then dried and cured to affix the hydrophilic agent, comprising the condensation product of the polycarboxylate and the cross-linking agent, to the fiber.
  • the fibers of the treated substrates are directly bonded to the hydrophilic carboxyl-containing polymers without the use of "activating reagents".
  • the treated fibrous substrates are thus endowed with hydrophilic characteristics, including improved water-wicking and breathability, in comparison to untreated substrates of the same fiber type.
  • This invention is further directed to synthetic or hydrophobic fibers, and yarns, fabrics, textiles, finished goods, or non-woven goods (encompassed herein under the terms "fibrous substrates", “textiles” or “webs”), which are treated with the hydrophilic treatment preparations of the invention.
  • the treated hydrophobic fibers and fibrous substrates exhibit hydrophilic characteristics in comparison to untreated substrates of the same fiber type.
  • a fibrous substrate is exposed to a solution that contains a polymer or oligomer that contains carboxyl, carboxylate, or carboxyl precursor groups (all of which polymers or oligomers are encompassed herein and in the claims under the terms "carboxyl-containing polymer” or "polycarboxylate”) as well as a cross-linking agent.
  • the treated substrate is then dried and cured to durably fix the hydrophilic agent, composed of the condensation product of the polycarboxylate and the cross-linking agent, to the fiber.
  • Wetting agents may be used to facilitate application of the polymer to the web, and a catalyst such as sodium hypophosphite may be added.
  • durable fix or “durable” is meant that the hydrophilic properties provided to the treated substrates by the treatment finish of the invention remain for at least about 10 home launderings, preferably for at least about 35 home launderings, and more preferably for at least about 50 home launderings.
  • the treatment is permanent; that is, the hydrophilic characteristics are present for the life of the treated fibrous substrate.
  • the carboxyl-containing polymers can be obtained through polymerization or copolymerization of one or more monomers that contain a carboxyl group, a carboxylate, or a group that can become a carboxyl or carboxylate group through a chemical reaction (a carboxyl precursor group).
  • Carboxyl precursors include, but are not limited to, acid chlorides, N-hydroxysuccinimidyl esters, amides, esters, nitriles, and anhydrides.
  • monomers with carboxyl precursor groups include (meth)acrylate chloride, (meth)acrylamide, N-hydroxysuccinimide (meth)acrylate, (meth)acrylonitrile, asparigine, and glutamine.
  • (meth)acryl indicates both the acryl- and methacryl- versions of the monomer.
  • Preferred carboxylate cations include aluminum, barium, chromium, copper, iron, lead, nickel, silver, strontium, zinc, zirconium, and phosphonium (R 4 P + ). More preferred cations include hydrogen, lithium, sodium, potassium, rubidium, ammonium, calcium, and magnesium.
  • the polymers may be linear or branched. In a presently preferred embodiment, the polymers are branched, and more preferably they have between about 0.001% and about 10% branching, inclusive.
  • Preferred monomers are acrylic acid, methacrylic acid and ⁇ -carboxyethyl acrylate.
  • Acrylate polymers containing carboxyl groups are commercially available.
  • poly(acrylic acid) is in wide production worldwide for use as a "super- absorbent" in disposable diapers and as a thickener in printing pastes.
  • Poly(acrylic acid) can be obtained from, among other sources, Polycryl AG, Bohler, Postfach, CH-6221 Rickenbach, Switzerland (trade name: Polycryl); Stockhausen, 2401 Doyle Street, Greensboro, NC, 27406-2911; and BFGoodrich, Four Coliseum Centre, 2730 West Tyvola Rd., Charlotte, NC 28217-4578 (trade name: Carbopol).
  • the presently preferred polycarboxylate is poly(acrylic acid) (PAA).
  • the present invention is further directed to synthetic or hydrophobic yarns, fibers, fabrics, finished goods, or other textiles (encompassed herein under the terms "fibrous substrates", “textiles” and “webs”) treated with the hydrophilic fabric finishes of the invention.
  • These textiles or webs will display characteristics usually associated with hydrophilic textiles (e.g. cotton), such as improved wettability and moisture breathability, while retaining the traditional advantages of synthetic textiles, such as strength and durability.
  • optical and other properties of the fiber may also be modified so as to, for example, reduce the shininess and improve the hand of synthetic fibers and fabrics.
  • Anti-static and stain release characteristics may also be imparted by treatment according to the invention.
  • the hydrophilic webs of the invention comprise (1) polymer chains that contain carboxyl groups, which have been simultaneously cross-linked together and affixed onto (2) synthetic or hydrophobic fibers formed into a fibrous substrate.
  • a catalyst may be added with the polymer to enhance the cross-linking and/or fixation of the polymer to the fiber.
  • the fibrous substrates of the present invention are intended to include fibers, fabrics and textiles, and may be sheet-like structures (woven, knitted, tufted, stitch-bonded, or non-woven) comprised of fibers or structural elements. Included with the fibers can be non-fibrous elements, such as particulate fillers, binders, and sizes.
  • the hydrophobic textiles or webs include fibers, woven and non-woven fabrics derived from natural or synthetic fibers or blends of such fibers. They can comprise hydrophobic fibers in the form of continuous or discontinuous monofilaments, multifilaments, staple fibers, and yarns containing such filaments and/or fibers, which fibers can be of any desired composition. Mixtures of natural fibers and synthetic fibers may also be used.
  • Examples of natural fibers include cotton, wool, silk, jute, and linen.
  • Examples of man-made fibers include regenerated cellulose rayon, cellulose acetate, and regenerated proteins.
  • Examples of synthetic fibers include, but are not limited to, polyesters (including polyethyleneterephthalate and polypropyleneterephthalate), polyamides (including nylon), acrylics, olefins, aramids, azlons, modacrylics, novoloids, nytrils, aramids, spandex, vinyl polymers and copolymers, vinal, vinyon, vinylon, Nomex ® (DuPont) and Kevlar ® (DuPont).
  • a synthetic or hydrophobic fiber, yarn, fabric, textile, finished good, or non-woven good (the "fibrous substrate” or “web") is exposed to a solution or suspension of the carboxyl- containing polymer or polycarboxylate and the cross-linker by methods known in the art, including soaking, spraying, dipping, fluid-flow, and padding.
  • the solution or suspension may optionally include, for example, cross-linking catalysts, defoamers, optical brighteners, dyestuffs, antibacterial agents, wetting agents.
  • the solvent may be water, an organic liquid, or a supercritical fluid.
  • the treated web is then removed from exposure, dried, and cured. The resulting web exhibits hydrophilic characteristics that are not present in the untreated web.
  • Such poiycarboxylates may be prepared by cross-linking lower molecular weight poiycarboxylates concurrently with the curing process.
  • the polycarboxylate polymers can be cross-linked together by including a cross-linking agent, a molecule that contains two or more carboxyl-reactive groups, in the treatment bath.
  • carboxyl-reactive groups include alcohols, amines, thiols, aminoplasts (e.g. condensation products of ureas and aldehydes), and oxazolines. It is desirable that the cross-linking agent be nonvolatile at or below the curing temperature; to this end, polymeric or high molecular weight cross-linking agents are of value.
  • cross-linking agent be soluble or readily suspended in the bath liquor.
  • alcohol cross-linking agents include glycerol and other non-polymeric polyols (including ⁇ , ⁇ - diols such as 1 ,5-pentanediol), poly(ethylene glycol), poly(vinyl alcohol) and poly(saccharides).
  • the poly(saccharides) may be either found in nature or derivatized from natural sources and may include celluloses, agars, pectins, xanthan gums and guar gums.
  • amine cross-linkers include polyamines, poly(vinyl amine) and poly(ethylene imine).
  • aminoplast cross-linkers examples include dimethyloldihydroxyurea (DMDHEU) and related urea- aldehyde condensation products as well as polymers containing aminoplast reactive groups.
  • oxazoline cross-linkers examples include the Epocros product line from Nippon Shokubai (2651 Riverport Rd. Chattanooga, TN 37406).
  • the precursors must be hydrolyzed to form carboxyl groups either during or after application of the finish to the textile.
  • Conditions for hydrolysis depend on the nature of the precursors. Preferably, the hydrolysis occurs at the pH and temperature conditions at which the fibrous substrate is treated, so as to facilitate formation of the carboxyl groups as the polymer is being applied to the textile or web.
  • Preferred precursor groups are acid chlorides and anhydrides. Less preferred precursor groups may require acidic or basic aqueous conditions and elevated temperatures for hydrolysis; such groups include esters and amides.
  • a preferred molecular weight of the carboxyl-containing polymer useful in the present invention is between about 90 and about 4,000 kilodaltons; a more preferred molecular weight is between about 125 and about 3,000 kilodaltons, and a most preferred molecular weight is between about 750 and about 1 ,250 kilodaltons. It is preferred that the polycarboxylate be cross-linked between about 0.001% and about 10%, more preferably between about 0.01% and about 1%. The molecular weight and degree of cross-linking can be obtained either prior to making the finish formulation or during the course of curing the finish onto the web.
  • the amount of carboxyl-containing polymer and other substituents in the treatment solution will depend on factors such as the particular polymer(s) used, the degree of hydrophilicity desired, and the like.
  • the carboxyl-containing polymer is present in the treatment solution in an amount of from about 0.001 wt. % to about 25 wt. %, preferably from about 0.005 wt. % to about 5 wt. %, more preferably from about 0.01 wt. % to about 2 wt. %.
  • the cross-linking agent is present in an amount from about 0.001 wt. % to about 10 wt. %, preferably from about 0.1 wt. % to about 5 wt.
  • the catalyst is present in an amount from 0 wt. % to about 4 wt. %, preferably from about 0 wt. % to about 2 wt. %, more preferably from about 0 wt. % to about 1.5 wt. %.
  • the wetting agent is present in an amount from 0 wt. % to about 5 wt. %, preferably from about 0.01 wt. % to about 1 wt. %, more preferably from about 0.05 wt. % to about 0.5 wt. %.
  • the process temperature can vary widely, depending on the reactivity of the reactants. However, the temperature should not be so high as to decompose the reactants or so low as to cause inhibition of the reaction or freezing of the solvent.
  • the textile is exposed to the polymer at atmospheric pressure over a temperature range between 5°C and 110°C, more preferably between 15°C and 60°C, and most preferably at room temperature, approximately 20° C.
  • the pH at which the carboxyl-containing polymer is applied may be between pH 0 to pH 7, preferably between pH 1 to pH 5, and more preferably between pH 2 to pH 4.5.
  • Curing conditions may range from 5° C to 250° C, preferably between 150° C and 200° C.
  • a square piece of fabric (approximately 2.5" x 6" or 6.4 cm x 15.2 cm) is placed in a metal canister with 100 stainless steel beads and 50 mL of 0.15 wt. % laundry detergent solution.
  • the canister is then rotated in a water bath at 71 °C.
  • Each nine-minute cycle in the Rotawash machine is taken as the equivalent of one home laundering (HL) in a conventional washing machine.
  • the sample is removed from the canister, rinsed with flowing tap water for 2 minutes, and dried in an oven at 100 °C.
  • the hydrophilicity/phobicity of a fabric swatch is determined by placing six drops of water on various locations on the swatch. The swatch is suspended so that the areas where the drops are placed are not in contact with any solid support or other material that could induce the wicking of water. The time required for each drop to soak into the fabric is measured, recorded and averaged. If the "time to soak" is greater than 120 seconds, the value is recorded as 120 seconds. The hydrophilicity of any particular swatch is determined by its average wicking time.
  • a 20.0 g aqueous solution of 1% alginic acid (Sigma-Aldrich), 0.6% sodium hypophosphite (Sigma-Aldrich), 0.5% 1 ,2,3,4-butanetetracarboxylic acid (Sigma- Aldrich), and 0.1% Wetaid NRW (Noveon) at pH 3.2 was prepared.
  • a nylon fabric swatch was dipped in the solution, padded at 25 psi, then dried and cured at 180 °C for five minutes. An untreated swatch was used as a control. A water drop placed on the treated fabric was absorbed in 71 seconds, whereas water required 303 seconds to soak into the untreated fabric.
  • the swatches were then washed by the Rotawash procedure as described herein for intervals of nine and forty-five minutes. After a nine-minute rotawash, a water drop was absorbed in 49 seconds on treated fabric, but required 239 seconds to soak into an untreated swatch. After an additional forty-five minute rotawash, the treated sample absorbed a water drop in 55 seconds, whereas the control required 216 seconds.
  • a 40.0 g aqueous solution of 0.5% alginic acid (Sigma-Aldrich), 0.5% polyethylene glycol (MW 200; Sigma-Aldrich), 0.5% sodium hypophosphite (Sigma- Aldrich), 0.5% 1 ,2,3,4-butanetetracarboxylic acid (Sigma-Aldrich), and 0.1 % Wetaid NRW (Noveon) at pH 3.5 was prepared. Nylon swatches were dipped in the solution, padded at 25 psi, then dried and cured for five minutes at 180 °C. A control swatch was dipped in water and treated similarly.
  • Treated swatches absorbed water drops with an average time of 28.5 seconds, while the control swatch required more than 360 seconds. The swatches were then washed for nine minutes in the Rotawash as described above. The treated swatches absorbed water drops with an average time of 93 seconds, whereas the control swatch required more than 390 seconds.
  • a 123.1 g 4% aqueous stock solution of poly(styrenesulfonic acid-co-maleic acid) (PSSA-co-MA) was prepared by dissolving 4.8 g poly(styrenesu!fonic acid-co- maleic acid), sodium salt (3:1 styrene:maleic, M w 20,000) in 118.3 g water. From this stock solution, 10.0 g solutions of 1 % PSSA-co-MA, 0.1 % Wetaid NRW (Noveon) and 0.5 % sodium hypophosphite (Sigma-Aldrich) with either 0.75 % or 1.5 % 1 ,5-pentanediol were prepared.
  • PSSA-co-MA poly(styrenesulfonic acid-co-maleic acid)
  • Swatches of nylon fabric were dipped in either solution, padded at 25 psi and dried/cured at 180 °C for five minutes.
  • a control swatch that was untreated was also prepared.
  • the hydrophilicity of each swatch was tested by placing six separate water drops on each fabric and noting the time required for each drop to soak in. The swatches were then washed by the Rotawash procedure for either 1 , 6 or 11 nine-minute cycles, after which they were dried and tested again for hydrophilicity.
  • the average wet time for each swatch is recorded in Table 2; swatches are designated by the amount of 1 ,5-pentanediol (1,5-pd) in the pad formulation.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne des apprêts de tissu ou des préparations pour traiter le nylon, le polyester et d'autres matériaux textiles et fibreux afin de les rendre hydrophiles. Les apprêts selon l'invention sont composés essentiellement de polymères qui contiennent des groupes carboxyle, des sels de groupes carboxyle ou des fractions pouvant être converties en groupes carboxyle par réaction chimique, ainsi que d'un agent de réticulation.
PCT/US2002/013783 2002-05-01 2002-05-01 Appret hydrophile pour supports fibreux WO2003093567A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002367913A AU2002367913A1 (en) 2002-05-01 2002-05-01 Hydrophilic finish for fibrous substrates
PCT/US2002/013783 WO2003093567A1 (fr) 2002-05-01 2002-05-01 Appret hydrophile pour supports fibreux

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2002/013783 WO2003093567A1 (fr) 2002-05-01 2002-05-01 Appret hydrophile pour supports fibreux

Publications (1)

Publication Number Publication Date
WO2003093567A1 true WO2003093567A1 (fr) 2003-11-13

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PCT/US2002/013783 WO2003093567A1 (fr) 2002-05-01 2002-05-01 Appret hydrophile pour supports fibreux

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AU (1) AU2002367913A1 (fr)
WO (1) WO2003093567A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7427300B2 (en) 2000-01-18 2008-09-23 Nano-Tex, Inc. Hydrophilic finish for fibrous substrates
CN102041686A (zh) * 2009-10-21 2011-05-04 山东魏桥创业集团有限公司 一种除臭免烫功能整理织物的制备方法
CN106958146A (zh) * 2016-01-08 2017-07-18 东丽纤维研究所（中国）有限公司 一种经过拒水处理的纺织品
US10161080B2 (en) * 2013-03-06 2018-12-25 Carl Freudenberg Kg Ventilation insert

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3948838A (en) * 1968-07-25 1976-04-06 Burlington Industries, Inc. Soil release composition
EP0164554A2 (fr) * 1984-05-14 1985-12-18 Kao Corporation Méthode pour traitement de textiles
JPS6359481A (ja) * 1986-08-28 1988-03-15 カネボウ株式会社 ポリエステル繊維構造物の吸水及び硬仕上加工方法
EP0945544A2 (fr) * 1998-03-24 1999-09-29 National Starch and Chemical Investment Holding Corporation Agent d'ennoblissement hydrophile pour textiles
JPH11293564A (ja) * 1998-04-09 1999-10-26 Toray Ind Inc オレフィン系不織布およびアルカリ二次電池用セパレーター

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3948838A (en) * 1968-07-25 1976-04-06 Burlington Industries, Inc. Soil release composition
EP0164554A2 (fr) * 1984-05-14 1985-12-18 Kao Corporation Méthode pour traitement de textiles
JPS6359481A (ja) * 1986-08-28 1988-03-15 カネボウ株式会社 ポリエステル繊維構造物の吸水及び硬仕上加工方法
EP0945544A2 (fr) * 1998-03-24 1999-09-29 National Starch and Chemical Investment Holding Corporation Agent d'ennoblissement hydrophile pour textiles
JPH11293564A (ja) * 1998-04-09 1999-10-26 Toray Ind Inc オレフィン系不織布およびアルカリ二次電池用セパレーター

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 198816, Derwent World Patents Index; Class A14, AN 1988-109820, XP002227416 *
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 01 31 January 2000 (2000-01-31) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7427300B2 (en) 2000-01-18 2008-09-23 Nano-Tex, Inc. Hydrophilic finish for fibrous substrates
CN102041686A (zh) * 2009-10-21 2011-05-04 山东魏桥创业集团有限公司 一种除臭免烫功能整理织物的制备方法
US10161080B2 (en) * 2013-03-06 2018-12-25 Carl Freudenberg Kg Ventilation insert
CN106958146A (zh) * 2016-01-08 2017-07-18 东丽纤维研究所（中国）有限公司 一种经过拒水处理的纺织品

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