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WO2001055499A1 - Traitement hydrofuge et oleofuge d'un textile - Google Patents

Traitement hydrofuge et oleofuge d'un textile Download PDF

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Publication number
WO2001055499A1
WO2001055499A1 PCT/JP2001/000243 JP0100243W WO0155499A1 WO 2001055499 A1 WO2001055499 A1 WO 2001055499A1 JP 0100243 W JP0100243 W JP 0100243W WO 0155499 A1 WO0155499 A1 WO 0155499A1
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WO
WIPO (PCT)
Prior art keywords
water
unit derived
structural unit
oil
chloride
Prior art date
Application number
PCT/JP2001/000243
Other languages
English (en)
Japanese (ja)
Inventor
Takashi Enomoto
Ikuo Yamamoto
Teruyuki Fukuda
Norihito Otsuki
Original Assignee
Daikin Industries, Ltd.
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 Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO2001055499A1 publication Critical patent/WO2001055499A1/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
    • D06M15/244—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
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • 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
    • 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 present invention relates to a treatment for imparting water repellency, oil repellency and antifouling property to textiles and their durability.
  • the method of the present invention is powerful. It is especially useful as a material.
  • U.S. Pat. No. 5,073,442 discloses a method for treating textile products by performing an Exhaust method using a water and oil repellent comprising a fluorine compound, a formaldehyde condensate, and an acrylic polymer.
  • U.S. Pat. No. 5,520,962 discloses a method for treating a carpet by performing an Exhaust method using a fluorine compound and a polymer binder.
  • U.S. Patent No. 5,516,337 discloses a method of treating textile products by performing an Exhaust method using a fluorine-based water / oil repellent and a metal compound such as aluminum sulfate.
  • International Publication WO 98/50619 discloses a method for treating a carpet by performing an Exhaust method using a fluorine-based water- and oil-repellent and a salt such as a magnesium salt.
  • An object of the present invention is to provide a product which is excellent in water repellency, oil repellency and antifouling properties, and durability thereof when an EX haust treatment is performed using a water repellent agent having a specific composition. .
  • the present invention is a.
  • a method for treating a textile product comprising:
  • A a fluorine-containing polymer having a constitutional unit derived from vinyl chloride and Z or vinylidene chloride; and (B) a fluorine-containing polymer having no constitutional unit derived from vinyl chloride and Z or vinylidene chloride.
  • a method comprising a combination of polymers is provided.
  • the present invention provides a ⁇ product obtained by the above method. Detailed description of the invention
  • the method used in the present invention comprises lowering ⁇ ⁇ of the treatment solution containing the fluoropolymer, applying the treatment solution to the product, heat-treating the ⁇ product, washing with water, and dehydrating ⁇ X haust Is the law.
  • a treatment liquid containing a water / oil repellent is prepared for application to textiles.
  • the treatment liquid containing the water and oil repellent may be in the form of a solution or an emulsion, especially an aqueous emulsion.
  • step (2) of the method of the present invention the pH of the treatment solution is adjusted to 7 or less.
  • the pH of the treatment liquid is preferably 3 or less, more preferably 2 or less.
  • an acid such as citraconic acid or sulfamic acid may be added to the treatment solution.
  • step (3) of the method of the present invention a treatment liquid is applied to the textile.
  • the water- and oil-repellent agent can be applied to an article to be treated) by a conventionally known method. place
  • the application of the physical solution can be carried out by dipping, spraying, coating or the like.
  • the treatment liquid is diluted with an organic solvent or water and applied to a cloth (eg, carpet fabric) or yarn (eg, carpet yarn) or fibrils by dip coating, spray coating, foam coating, etc. Is attached to the surface of the object to be treated.
  • the composition may be applied together with an appropriate crosslinking agent and cured.
  • insect repellents, softeners, antibacterial agents, flame retardants, antistatic agents, paint fixing agents, screen inhibitors, etc. can be used in combination.
  • the concentration of the water- and oil-repellent active ingredient (that is, the fluoropolymer) in the treatment liquid brought into contact with the object to be treated may be 0.05 to 10% by weight.
  • the stain blocking agent may be used in an amount of, for example, 0 to 100 parts by weight, particularly 1 to 500 parts by weight, based on 100 parts by weight of the fluoropolymer in terms of solid content. Les ,.
  • step (4) of the method of the present invention the textile is subjected to a heat treatment.
  • the heat treatment can be performed, for example, by applying steam (for example, 90 to 110 ° C.) to the textile at normal pressure, for example, for 10 seconds to 10 minutes.
  • step (5) of the method of the present invention the textile is washed with water and dehydrated. Rinse cooked product with at least one wash of water. Then, in order to remove excess water, dehydration is performed by a usual dehydration method, for example, centrifugation, vacuum or the like. After step (5): 3 ⁇ 4 The product can be dried.
  • the water- and oil-repellent used in the present invention comprises two types of fluoropolymers, namely a fluoropolymer ( ⁇ ) and a fluoropolymer ( ⁇ ).
  • the fluoropolymer ( ⁇ ) is a fluoropolymer having a structural unit derived from vinyl chloride and ⁇ or vinylidene chloride.
  • the fluorine-containing polymer ( ⁇ ) is a fluorine-containing polymer having no structural unit derived from butyl chloride and ⁇ or vinylidene chloride.
  • the fluoropolymers ( ⁇ ) and ( ⁇ ) are monomers having a fluoroalkyl group, for example, a (meth) acrylate having a fluoroalkyl group, a maleate or a fumarate having a fluoroalkyl group or a urethane having a fluoroalkyl group. It may be a polymer having units.
  • the fluoropolymer ( ⁇ ) is, for example,
  • (A-II) It may be a copolymer having a constitutional unit derived from vinyl chloride and ⁇ or vinylidene chloride.
  • An example of the fluoropolymer ( ⁇ ) is
  • the fluoropolymer (B) is, for example,
  • It may be a polymer having no structural units derived from vinyl chloride and / or vinylidene chloride.
  • An example of the fluorinated polymer (B) is
  • B-I a structural unit derived from a monomer containing a fluoroalkyl group
  • B-II a structural unit derived from a monomer containing no fluorine
  • the structural units (A-I) and (B-1) are preferably structural units derived from a (meth) acrylic acid ester containing a fluoroalkyl group.
  • the fluoroalkyl group-containing (meth) acrylic acid ester may be represented by the following general formula.
  • R f -A-OCOCR 1 1 CH 0
  • R f is a fluoroalkyl group having 3 to 21 carbon atoms
  • R 11 is a hydrogen or methyl group
  • A is a divalent organic group.
  • A is a linear or branched alkylene group having 1 to 20 carbon atoms, one S0 2 N (R 2 R 22 — group or one CH 2 CH (OR 23 ) CH 2 —Group (where R 21 is an alkyl group having 1 to 10 carbon atoms, R 22 is a 1 to 10 carbon atom R 23 is a hydrogen atom or an acyl group having 1 to 10 carbon atoms. ).
  • fluoroalkyl group-containing (meth) acrylate examples include the following.
  • Rf is a fluoroalkyl group having 3 to 21 carbon atoms
  • R 1 is hydrogen or an alkyl group having 1 to 10 carbon atoms
  • R 2 is an alkylene group having 1 to 10 carbon atoms
  • R 3 is a hydrogen or methyl group
  • Ar is an arylene group which may have a substituent
  • n is an integer of 1 to 10.
  • the constituent units (A-II) and (B-11) are preferably derived from a fluorine-free vinylinole monomer.
  • Good to form the structural units (A-III) and (B-B) Preferred monomers include, for example, ethylene, vinyl acetate, acrylonitrile, styrene, alkyl (meth) acrylate, polyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, methoxy polyethylene glycol (meta).
  • the monomers forming the structural units (A-111) and (B-11) may be (meth) acrylates containing an alkyl group.
  • the alkyl group may have 1 to 30 carbon atoms, for example, 6 to 30 carbon atoms, for example, 10 to 30 carbon atoms.
  • the monomers forming the structural units (A—I I I) and (B—II) have the general formula:
  • a 1 is a hydrogen atom or a methyl group
  • the crosslinkable monomer forming the structural units (A-IV) and (B-III) may be a fluorine-free vinyl monomer having at least two reactive groups.
  • the crosslinkable monomer may be a compound having at least two carbon-carbon double bonds, or a compound having at least one carbon-carbon double bond and at least one reactive group.
  • crosslinking monomer examples include diacetone acrylamide, (meth) acrylamide, N-methylol acrylamide, hydroxymethyl (meth) acrylate, hydroxyshethyl (meth) acrylate, and 3-chloro-2 —Hydroxypropyl
  • Examples include (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, N-getylaminoethyl (meth) acrylate, butadiene, chloroprene, and dalicydyl (meth) acrylate. Not limited to these.
  • water and oil repellency and antifouling properties and Various properties such as cleaning resistance, washing resistance, solubility in a solvent, hardness, and feel can be improved as required.
  • the weight average molecular weight of the fluorinated polymer (A) and the fluorinated polymer (B) is preferably from 2000 to 1,000,000, for example, from 10,000 to 200,000 (for the copolymer (A),
  • the amount of the structural unit (A- I) is 40 to 89.9 wt 0/0, more preferably 50 to 79.5 the structural unit amount of (A- II) is 5 to 50 wt 0/0, more preferably 10 40 wt 0/0, the amount is from 5 to 54.9 weight of the structural unit (A- III). / 0 , more preferably 10-40% by weight,
  • the amount of the structural unit (A-IV) is 0.1 to 10% by weight, more preferably 0.5 to 5% by weight.
  • the amount of constituent units (B-I) is 39-94.9 weight 0 /. , More preferably 50-89.5% by weight,
  • Structural units amount from 5 to 60 wt% of (B- II), more preferably 10 to 40 wt%, the amount of the structural unit (B- III) is 0.. 1 to: L 0 Weight 0/0, more preferably 0. it is preferable that 5 to 5 weight 0/0.
  • the weight ratio of the fluoropolymer (A) to the fluoropolymer (B) is 1:99 to 99: 1, for example, 10:90 to 90:10, particularly 70:30 to 9
  • the fluoropolymers (A) and (B) in the present invention can be produced by any ordinary polymerization method, and the conditions for the polymerization reaction can be arbitrarily selected.
  • Such polymerization methods include solution polymerization and emulsion polymerization. Emulsion polymerization is particularly preferred.
  • a monomer (A-I), a monomer (A-III) and a crosslinkable monomer (A-IV) are dissolved in an organic solvent in the presence of a polymerization initiator.
  • Vinyl chloride and Z or vinylidene chloride (A-II) are charged, and the mixture is heated and stirred at 50 to 120 ° C for 1 to 10 hours.
  • a polymerization initiator for example, examples thereof include azobisisobutyronitrile, benzoyl peroxide, di-tert-butyl peroxide, lauryl peroxide, cumene drop-oxide, t-butyl peroxy pivalate, disopropyl peroxide dicarbonate and the like.
  • the polymerization initiator is used in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the monomer.
  • Organic solvents which are inactive in monomers and dissolve them such as pentane, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, petroleum ether, tetrahydrofuran, 4-dioxane, methylethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, 1,1,2,2-tetrachloroethane, 1,1,1-trichloroethane, trichloroethylene, and Monochloroethylene, tetrachlorodiphnoleroethane, trichlorotriphnoleoethane, and the like.
  • the organic solvent is used in the range of 50 to 100 parts by weight based on 100 parts by weight of the monomers (A-I) to (A-IV).
  • a monomer (A-I), a monomer (A-III) and a crosslinkable monomer (A-IV) are emulsified in water in the presence of a polymerization initiator and a simulant, After the replacement with nitrogen, a method is adopted in which vinyl chloride and Z or vinylidene chloride (A-II) are charged, and the mixture is stirred at 50 to 80 ° C for 1 to 10 hours for copolymerization.
  • the polymerization initiator is used in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the monomer.
  • an emulsifying device such as a high-pressure homogenizer or ultrasonic homogenizer that can apply a strong crushing energy. It is desirable to polymerize using a water-soluble polymerization initiator. Good. Also, ? Various anionic, cationic or nonionic emulsifiers can be used as the precipitating agent. The emulsifier is used in an amount of 0.5 to 10 parts by weight per 100 parts by weight of the monomer.
  • a compatibilizing agent that can sufficiently dissolve the monomers (for example, a water-soluble organic solvent or a low molecular weight) is used. Is preferred. By adding a compatibilizer, it is possible to improve the stiffness and copolymerizability.
  • water-soluble organic solvent examples include acetone, methyl ethyl ketone, ethyl acetate, propylene glycol, dipropylene glycol monomethizoleate, dipropylene glycol, tripropylene glycol, and ethanol. It may be used in an amount of 1 to 50 parts by weight, for example, 10 to 40 parts by weight based on 0 parts by weight.
  • the fluorinated polymer (B) can be produced by the same procedure as that for the fluorinated polymer (A) except that butyl chloride and divinylidene chloride are not used. By separately mixing the liquid containing the fluoropolymer (A) and the liquid containing the fluoropolymer (B), and adding a medium (for example, water or an organic solvent) if necessary, A water and oil repellent is obtained.
  • a medium for example, water or an organic solvent
  • the article to be treated is a product, particularly preferably a pet.
  • a product particularly preferably a pet.
  • animal and plant natural fibers such as cotton, hemp, wool, and silk
  • synthetic fibers such as polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride, and polypropylene
  • semi-synthetic fibers such as rayon and acetate
  • glass fibers glass fibers
  • Inorganic materials such as carbon fiber and Asbest » or a mixture thereof.
  • the method of the present invention provides excellent resistance to detergent solutions, brushing (mechanical), and thus can be suitably used for power tips made of nylon ⁇ , polypropylene and / or polyester ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ .
  • the textile product may be in any form of fiber, cloth, and the like.
  • the carpet In the case of treating the power unit with a water / oil repellent, the carpet may be formed after treating the fiber or yarn with the water / oil repellent, or the formed carpet may be repelled. It may be treated with a water repellent.
  • the objects that can be treated are «products, glass, paper, wood, leather, fur, asbestos, bricks, cement, metals and oxides, ceramic products, plastics, painted surfaces, And plaster. Preferred embodiments of the invention
  • test procedures for water repellency, oil repellency, antifouling properties, fluorine adhesion and cleaning are as follows.
  • a pet repellent treated pet into a thermo-hygrostat at 21 ° C and a humidity of 65% for at least 4 hours.
  • the test solution (of the composition in Table 1) is also kept at 21 ° C. Adjust the temperature of the measuring chamber to about 21 ° C.
  • the solution is dropped at 5 O / il with a micropipeter (droplet diameter is 5). Hold the micropipet vertically and gently drop the liquid. Drop 5 drops. If 4 or 5 drops remain after 10 seconds, the test solution shall be passed. Water repellency, the maximum content of isopropyl alcohol passes the test solution (IPA) (volume 0/0).
  • Hexa ⁇ can 35 parts by weight
  • the L * a * and b * of the carpet test piece from which excess Soil was removed by suction were measured using a color difference meter (Minolta Co., Ltd., color difference meter CR-310, the detection unit was a 50-diameter circle). Measure at 5 points for each test specimen. From L *, a *, and b * before the antifouling test and L *, a *, and b * after the antifouling test, calculate the color difference ( ⁇ ) using the following formula. Since each force is measured at 5 points on each test piece, calculation is performed using the same values.
  • the fluorine content (ppm) present on the carpet fiber is measured by the oxyfuel combustion method.
  • the pet of the present invention has a water repellency of 90 or more and an oil repellency of 5 or more before cleaning, and a water repellency of 40 or more and an oil repellency of 2 or more after 10 times of cleaning. Preferably, there is.
  • Production Example 1 Production of fluorinated water / oil repellent (a) containing vinyl chloride
  • a carpet (8.9 x 18.2 cm, Nylon 6, 6, Cut No., density 36 oz / yd 2) is immersed in this treatment solution for 30 seconds, and the amount of WPU (wet pick up) becomes 300%. I squeezed it.
  • normal pressure steam treatment temperature 100 to 107 ° C
  • centrifugal dehydration was performed to reduce the amount of WPU to about 25%.
  • heat curing was performed at 110 ° C for 10 minutes. Next, this car The samples were cleaned (5 times and 10 times), and the water repellency, oil repellency, antifouling property, and fluorine adhesion before and after cleaning were evaluated. The results are shown in Tables A to D. Comparative Example 1
  • emulsion repellent agent solid content concentration: 2 1 wt%) [fluoric oil-repellent agent containing chlorine (6 wt 0/0) and Augustin blocking agent (phenol one formaldehyde condensate)
  • emulsion repellent agent solid content concentration: 2 1 wt%) [of the fluoric oil repellent agent containing chlorine (6 wt 0/0) and Augustin blocking agent (phenol one formaldehyde condensate) (1 5% by weight) 5.7 g of MgS04 and 12.5 g of MgS04 were diluted to 1000 g with water to obtain a mixed solution. A 10% aqueous solution of sulfamic acid was added to the mixture to adjust the pH to 1.5. did. Processing and evaluation were performed in the same manner as in Comparative Example 1. The results are shown in Tables A to D. Table A
  • the untreated carpet has a delta E value of 25.6 with zero cleaning.

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

Abstract

L'invention porte sur un produit textile très durable présentant avant et après lavage des qualités hydrofuges et oléofuges et d'insensibilité à l'encrassement, suite au traitement suivant: (1) préparation d'un liquide de traitement incluant un hydrofuge/oléofuge; (2) fixation du pH dudit liquide à 7 ou moins; (3) application du liquide au produit; (4) passage du produit textile à la vapeur, et (5) lavage à l'eau puis déshydratation du produit textile résultant. Le susdit liquide est une combinaison de (A) un fluoropolymère présentant des unités structurelles dérivant du chlorure de vinyle et/ou du chlorure de vinylidène, et de (B) un fluoropolymère ne contenant pas d'unités structurelles dérivant du chlorure de vinyle et/ou du chlorure de vinylidène.
PCT/JP2001/000243 2000-01-25 2001-01-17 Traitement hydrofuge et oleofuge d'un textile WO2001055499A1 (fr)

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JP2000015769 2000-01-25

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Cited By (2)

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US6777059B2 (en) 2002-03-13 2004-08-17 E.I. Du Pont De Nemours And Company Treated poly(trimethylene terephthalate) carpets
US7678155B2 (en) * 2003-04-08 2010-03-16 Daikin Industries, Ltd. Water- and oil-repellent treatment of textile

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US7652112B2 (en) 2005-07-06 2010-01-26 E.I. Du Pont De Nemours And Company Polymeric extenders for surface effects
SG172905A1 (en) * 2009-01-07 2011-08-29 Beaulieu Group Llc Method and treatment composition for imparting durable antimicrobial properties to carpet
EP2682178B1 (fr) 2011-02-28 2021-01-27 Nitto Denko Corporation Filtre de ventilation oléofuge
JP6037643B2 (ja) * 2012-04-06 2016-12-07 日東電工株式会社 撥油性が付与された通気フィルム
US9534343B2 (en) * 2012-10-18 2017-01-03 The Chemours Company Fc, Llc Partially fluorinated copolymer emulsions containing fatty acids and esters
JP7157307B2 (ja) * 2018-05-11 2022-10-20 ダイキン工業株式会社 撥水撥油剤および繊維製品

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JPS5933380A (ja) * 1982-08-20 1984-02-23 Nippon Mektron Ltd 撥水撥油剤
JPH08199111A (ja) * 1995-01-26 1996-08-06 Asahi Glass Co Ltd 防汚性の改良された撥水撥油剤組成物
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6777059B2 (en) 2002-03-13 2004-08-17 E.I. Du Pont De Nemours And Company Treated poly(trimethylene terephthalate) carpets
US7678155B2 (en) * 2003-04-08 2010-03-16 Daikin Industries, Ltd. Water- and oil-repellent treatment of textile

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