WO2015194049A1 - Composition hydrofuge et oléofuge et procédé de production pour produit textile hydrofuge et oléofuge - Google Patents

Composition hydrofuge et oléofuge et procédé de production pour produit textile hydrofuge et oléofuge Download PDF

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Publication number
WO2015194049A1
WO2015194049A1 PCT/JP2014/066474 JP2014066474W WO2015194049A1 WO 2015194049 A1 WO2015194049 A1 WO 2015194049A1 JP 2014066474 W JP2014066474 W JP 2014066474W WO 2015194049 A1 WO2015194049 A1 WO 2015194049A1
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monomer
water
oil repellent
oil
repellent composition
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PCT/JP2014/066474
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English (en)
Japanese (ja)
Inventor
吉野　豪
西川　誠
旻時 鄭
恵媛 ▲ベ▼
智赫 任
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日華化学株式会社
ニッカ コリア カンパニー リミテッド
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Priority to PCT/JP2014/066474 priority Critical patent/WO2015194049A1/fr
Publication of WO2015194049A1 publication Critical patent/WO2015194049A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces

Definitions

  • the present invention relates to a water / oil repellent composition capable of imparting water / oil repellency to a fiber product and a method for producing a water / oil repellent fiber product.
  • a water- and oil-repellent component having a perfluoroalkyl group having 8 carbon atoms is perfluorooctane sulfonic acid (C 8 H 17 SO 2), which has been concerned about degradation when it is discharged into the environment.
  • F hereinafter abbreviated as PFOS
  • PFOA perfluorooctanoic acid
  • PFOS PFOA
  • perfluoroalkanesulfonic acid having more than 8 carbon atoms or perfluoroalkanoic acid is not generated.
  • Alternatives to water- and oil-repellent components having an alkyl group are being studied.
  • Patent Documents 1 to 3 contain (meth) acrylate having a perfluoroalkyl group having 6 or less carbon atoms as a copolymer component.
  • a water / oil repellent composition comprising a copolymer is disclosed.
  • the water / oil repellency component having a perfluoroalkyl group having 6 or less carbon atoms tends to be inferior in water / oil repellency and durability compared to those having 8 or more carbon atoms.
  • Patent Documents 1 to 3 a specific monomer containing a polyfluoroalkyl group and a specific compound not containing a polyfluoroalkyl group are included in order to improve the water / oil repellency, durability and texture of the processed product. It is described that the monomer is copolymerized.
  • the object of the present invention has been made in view of the above circumstances, and by using a water / oil repellent component having a perfluoroalkyl group having 6 or less carbon atoms, good water / oil repellency and its durability and processing stability. It is an object of the present invention to provide a water / oil repellent composition capable of imparting properties and texture, and a method for producing a water / oil repellent fiber product using the composition.
  • the present inventors have obtained, as a water / oil repellent component, a specific monomer having a C 6 perfluoroalkyl group, a specific copolymer component,
  • the water / oil repellent composition containing a copolymer obtained by copolymerizing a specific monomer composition containing a water / oil repellent component having a perfluoroalkyl group having 6 or less carbon atoms, It has been found that good water and oil repellency and its durability, processing stability and texture can be provided, and the present invention has been completed based on this finding.
  • the water / oil repellent composition of the present invention comprises the following monomer (A) and the following monomer (B), or the following monomer (A), the following monomer (B) and the following monomer ( C), the blending ratio (mass ratio) of the monomer (A) and the monomer (B) is 95: 5 to 80:20, and the monomer (A) and the monomer (B) And a copolymer obtained by copolymerizing a monomer composition in which the blending ratio (mass ratio) of the total of the monomer and the monomer (C) is 100: 0 to 60:40.
  • the water / oil repellent composition of the present invention by containing the copolymer having the above-described structure, it is possible to impart good water / oil repellency and durability, processing stability and texture to textiles and the like. Can do.
  • the water / oil repellent composition of the present invention is a monomer having a perfluoroalkyl group having 6 or less carbon atoms, particularly compared to a conventional water / oil repellent component having a perfluoroalkyl group having 6 or less carbon atoms. The above performance can be satisfied when the blending ratio is large.
  • the water / oil repellent composition of the present invention is the sum of the monomer (A) and the monomer (B) and the unit amount from the viewpoints of water / oil repellency and durability, texture, and processing stability.
  • the blending ratio (mass ratio) with the body (C) is preferably 95: 5 to 60:40.
  • the present invention also provides a method for producing a water / oil repellent fiber product comprising a step of treating a fiber product with a treatment liquid containing the water / oil repellent composition according to the present invention.
  • a water and oil repellency component having a perfluoroalkyl group having 6 or less carbon atoms can be used to provide good water and oil repellency, durability, processing stability and texture.
  • An oil repellent composition and a method for producing a water / oil repellent fiber product using the composition can be provided.
  • the water / oil repellent composition of the present invention compared to the conventional water / oil repellent component having a perfluoroalkyl group having 6 or less carbon atoms, it has better water / oil repellency and its durability, processing stability and texture. Can be given to textile products and the like.
  • (meth) acrylate means both acrylate and methacrylate.
  • the water / oil repellent composition of the present embodiment includes the following monomer (A) and the following monomer (B), or the following monomer (A), the following monomer (B), and the following monomer.
  • C the blending ratio (mass ratio) of the monomer (A) and the monomer (B) (hereinafter sometimes referred to as “monomer (A): monomer (B)”) ) Is 95: 5 to 80:20, and the blending ratio (mass ratio) of the monomer (A) and the monomer (B) to the monomer (C) (hereinafter referred to as “monomer ( A) + monomer (B): monomer (C) ”may be abbreviated as 100) to 60:40, and a copolymer obtained by copolymerizing a monomer composition is contained. .
  • Monomer (A) At least one monomer represented by the following general formula (1).
  • C 6 F 13 (CH 2) n OC (O) C (R 1) CH 2 ... (1)
  • n represents 2 or 3
  • R 1 represents hydrogen or a methyl group.
  • the monomer (A) can be obtained, for example, by an esterification reaction between perfluorohexyl ethyl alcohol and methacrylic acid. Also commercially available such as Cheminox FAMAC-C (Unimatec Co., Ltd.), 2- (perfluorohexyl) -ethyl methacrylate (Daikin Chemicals Sales), 2- (perfluorohexyl) -ethyl methacrylate (Aldrich) Product can be used.
  • Such monomers (A) can be used singly or in combination of two or more.
  • the monomer (B) is preferably at least one selected from the group consisting of isobornyl acrylate and isobornyl methacrylate from the viewpoint of water / oil repellency and its durability, texture, and processing stability. More preferred is isobornyl methacrylate.
  • Such monomers (B) can be used singly or in combination of two or more.
  • the monomer (C) is at least one monomer selected from the group consisting of vinyl halides and vinylidene halides from the viewpoints of water / oil repellency and durability, texture, and processing stability. preferable.
  • the vinyl halide and vinylidene halide include vinyl chloride, vinyl bromide, vinylidene chloride, and vinylidene bromide. Among these, vinyl chloride and / or vinylidene chloride are preferable from the viewpoint of water / oil repellency and durability.
  • These monomers (C) can be used alone or in combination of two or more.
  • a monomer (C) other than vinyl halide and vinylidene halide is used as the monomer (C)
  • a monomer other than vinyl halide and vinylidene halide contained in the monomer composition to be copolymerized The content of the body (C) is preferably 15% by mass or less, more preferably 5% by mass or less, based on the total amount of the monomer composition, from the viewpoints of water / oil repellency and durability, texture, and processing stability. preferable.
  • the copolymer according to this embodiment is not particularly limited in the arrangement of monomers (structural units), and may be a random copolymer, a block copolymer, or an alternating copolymer.
  • the copolymer according to this embodiment preferably has a melt viscosity at 105 ° C. of 5 to 20000 Pa ⁇ s, and more preferably 10 to 10,000 Pa ⁇ s.
  • a melt viscosity at 105 ° C. of 5 to 20000 Pa ⁇ s, and more preferably 10 to 10,000 Pa ⁇ s.
  • the melt viscosity can be measured at a measurement temperature of 105 ° C. using a flow tester CFT-500D (manufactured by SHIMADZU).
  • the copolymer according to the present embodiment can be obtained by applying a conventionally known copolymerization method.
  • a conventionally known copolymerization method examples thereof include a solution polymerization method using an organic solvent as a solvent, and an emulsion polymerization method using water as a solvent and containing an organic solvent and various surfactants.
  • organic solvent examples include aliphatic alcohols having 1 to 8 carbon atoms such as methanol, ethanol, isopropanol, n-butanol, 2-butanol, t-butanol, n-hexanol, 2-ethylhexanol, glycerin; ethylene glycol, diethylene glycol , Glycols such as triethylene glycol, propylene glycol, tripropylene glycol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl Ether, diethylene glycol monobutyl ether, triethyleneglycol Glycol ethers such as dimethyl monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol; glycol esters such as
  • At least one selected from the group consisting of glycols and glycol ethers is preferable from the viewpoint of water / oil repellency, product stability, processing stability, and permeability of the treatment liquid into the fiber product.
  • Tripropylene glycol and polypropylene glycol are more preferable from the viewpoint of product stability, and diethylene glycol monobutyl ether is even more preferable from the viewpoint of processing stability.
  • the above solvents can be used singly or in combination of two or more. When using in combination of 2 or more types, it is preferable to mix and use with water. It is preferable to use a mixed solvent containing water and an organic solvent because the solubility and emulsification dispersibility of the copolymer can be easily controlled, and the permeability to the fiber product can be easily controlled during processing.
  • the blending amount of the organic solvent is preferably 3 to 20% by mass, more preferably 5 to 10% by mass with respect to the water / oil repellent composition. .
  • the surfactant it is preferable to use a cationic surfactant, a nonionic surfactant, an amphoteric surfactant or the like.
  • Examples of cationic surfactants include monoalkyltrimethylammonium salts having 8 to 24 carbon atoms, dialkyldimethylammonium salts having 8 to 24 carbon atoms, monoalkylamine acetates having 8 to 24 carbon atoms, and dialkylamines having 8 to 24 carbon atoms. Examples thereof include acetates and alkyl imidazoline quaternary salts having 8 to 24 carbon atoms. Among these, from the viewpoints of emulsifying properties and processing stability, monoalkyltrimethylammonium salts having 12 to 18 carbon atoms and dialkyldimethylammonium salts having 12 to 18 carbon atoms are preferable.
  • cationic surfactants can be used singly or in combination of two or more.
  • nonionic surfactants include alcohols, polycyclic phenols, amines, amides, fatty acids, polyhydric alcohol fatty acid esters, fats and oils, and alkylene oxide adducts of polypropylene glycol.
  • alcohols examples include linear or branched alcohols having 8 to 24 carbon atoms or alkenols.
  • polycyclic phenols monohydric phenols such as phenol and naphthol which may have a hydrocarbon group having 1 to 12 carbon atoms or styrenes thereof (styrene, ⁇ -methylstyrene, vinyltoluene) are added. Or their benzyl chloride reactants.
  • amines include linear or branched aliphatic amines having 8 to 44 carbon atoms.
  • amides include linear or branched fatty acid amides having 8 to 44 carbon atoms.
  • fatty acids include linear or branched fatty acids having 8 to 24 carbon atoms.
  • polyhydric alcohol fatty acid esters examples include a condensation reaction product of a polyhydric alcohol and a linear or branched fatty acid having 8 to 24 carbon atoms.
  • oils and fats include vegetable oils, animal fats and oils, vegetable waxes, animal waxes, mineral waxes, hydrogenated oils, and the like. Among these, from the viewpoints of little influence on water and oil repellency, little influence on light resistance, and good emulsifiability of the copolymer, linear or branched alcohol having 8 to 24 carbon atoms or Alkenol is preferable, and linear or branched alcohol having 8 to 24 carbon atoms is more preferable.
  • alkylene oxide examples include ethylene oxide, 1,2-propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, 1,4-butylene oxide, styrene oxide, epichlorohydrin and the like. From the viewpoint of little influence on water and oil repellency and good emulsifiability of the copolymer, the alkylene oxide is preferably ethylene oxide or 1,2-propylene oxide, and more preferably ethylene oxide.
  • the number of added moles of alkylene oxide is preferably 1 to 200, more preferably 3 to 100, and even more preferably 5 to 50.
  • the added mole number of alkylene oxide is less than 1 mole, product stability and water / oil repellency tend to be lowered, and when it exceeds 200 moles, water / oil repellency tends to be lowered.
  • HLB (molecular weight of hydrophilic group in nonionic surfactant ⁇ 20) / molecular weight of nonionic surfactant
  • Nonionic surfactants can be used singly or in combination of two or more. When two or more types are used in combination, it is preferable to use a nonionic surfactant so that the weighted average HLB is 8 to 16, and in this case, a better aqueous dispersion can be obtained.
  • various surfactants may be used singly or in combination of two or more, but the emulsifying dispersibility of the monomer at the time of copolymerization, the emulsifying dispersibility of the copolymer From the viewpoints of processing stability and water / oil repellency, it is preferable to use a cationic surfactant and a nonionic surfactant in combination.
  • the surfactant is preferably contained in an amount of 1 to 20% by mass based on the copolymer, and preferably 3 to 16% by mass based on the copolymer.
  • amount is less than 1% by mass, the processing stability tends to decrease.
  • it exceeds 20 mass% there exists a tendency for water and oil repellency and its durability to fall.
  • copolymer solution and emulsion dispersion thus obtained may be used as they are or after dilution. Further, after separating the copolymer, it may be used after being dissolved or emulsified and dispersed in a solvent.
  • a high-pressure emulsifier for example, it is preferable to mix and disperse a mixture comprising a monomer, a surfactant, an organic solvent, water and the like with a homomixer or a high-pressure emulsifier. It is preferable to mix and disperse the raw material mixture in advance before the start of polymerization because the processing stability of the finally obtained water / oil repellent composition is improved.
  • a radical polymerization initiator In starting the polymerization reaction, heat, light, radiation, a radical polymerization initiator, an ionic polymerization initiator, or the like is preferably used.
  • a water-soluble or oil-soluble radical polymerization initiator is preferable, and general-purpose initiators such as an azo polymerization initiator, a peroxide polymerization initiator, and a redox initiator can be used depending on the polymerization temperature.
  • an azo compound is particularly preferable, and when polymerization is performed in a solvent using water, a salt of an azo compound is more preferable.
  • the polymerization temperature is not particularly limited, but is preferably 20 to 150 ° C, more preferably 50 to 70 ° C.
  • a molecular weight modifier may be used.
  • aromatic compounds or mercaptans are preferable, and alkyl mercaptans are more preferable.
  • the copolymer is preferably dispersed as particles in a solvent.
  • the average particle size is preferably 10 to 1000 nm, more preferably 50 to 300 nm, and even more preferably 80 to 200 nm from the viewpoints of water / oil repellency and product stability.
  • the average particle size was determined by using a laser diffraction type / scattering type particle size distribution measuring device LA-920 (manufactured by Horiba, Ltd.), and the percentage integrated value of the copolymer particle size was 50% from the small particle size side.
  • the average particle diameter can be measured.
  • the water / oil repellent composition of the present embodiment preferably contains a solvent from the viewpoint of easy handling.
  • a solvent the solvent similar to the solvent which can be used in order to obtain the copolymer mentioned above can be used.
  • the content of the solvent in the water / oil repellent composition is preferably from 50 to 90 mass%, more preferably from 55 to 75 mass%, based on the entire composition.
  • the content of the organic solvent is preferably 1 to 20% by mass, more preferably 5 to 15% by mass based on the whole composition.
  • a water / oil repellent fiber product can be obtained by treating the fiber product with a treatment liquid containing the water / oil repellent composition of the present embodiment.
  • the water / oil repellent composition of the present embodiment can be used as a treatment liquid as it is, or can be diluted with water or an organic solvent to obtain a treatment liquid.
  • the treatment liquid according to the present embodiment contains 0.3 to 5% by mass of the water / oil repellent composition of the present embodiment from the viewpoint that the amount of the water / oil repellent composition applied to the fiber product can be easily controlled. It is preferable that
  • the treatment liquid according to the present embodiment contains an organic solvent.
  • an organic solvent the organic solvent similar to the organic solvent which can be used in order to obtain the said copolymer can be used.
  • diethylene glycol monobutyl ether can be suitably used from the viewpoint of processing stability and permeability to fiber products.
  • the organic solvent is preferably contained in the treatment liquid in an amount of 0.3 to 3% by mass, more preferably 0.5 to 1.5% by mass based on the total amount of the treatment liquid.
  • the water / oil repellent composition of the present embodiment preferably has a pH of 2.0 to 6.0 from the viewpoint of water / oil repellency, texture and processing stability.
  • the treatment liquid according to this embodiment preferably has a pH of 3.0 to 7.0, and preferably 3.0 to 6.0, from the viewpoint of water / oil repellency, texture, and processing stability. Is more preferable.
  • the pH adjustment of the water / oil repellent composition of the present embodiment and the treatment liquid according to the present embodiment can be adjusted to an arbitrary pH by using a pH adjuster.
  • a pH adjuster acids such as formic acid, acetic acid, malic acid and citric acid; alkalis such as caustic soda, sodium carbonate and aqueous ammonia can be used.
  • alkalis such as caustic soda, sodium carbonate and aqueous ammonia
  • a penetrant When processing the treatment liquid according to the present embodiment into a textile product, a penetrant, an antifoaming agent, an antistatic agent, a texture adjusting agent, a melamine resin, an isocyanate compound, a glyoxal resin, a catalyst, and the like are included in the treatment liquid. You may use together.
  • the treatment liquid according to the present embodiment can be produced, for example, by mixing water, an organic solvent, and the water / oil repellent composition of the present embodiment.
  • the order of mixing is not particularly limited, but from the viewpoint of processing stability, a method of mixing an organic solvent diluted with water and the water / oil repellent composition of the present embodiment diluted with water, or organic A method of diluting one of the solvent or the water / oil repellent composition of the present embodiment with water and then mixing the other is preferred.
  • the method for producing a water / oil repellent fiber product of this embodiment includes a step of treating the fiber product with a treatment liquid containing the water / oil repellent composition of this embodiment.
  • a conventionally performed method can be used without limitation. Examples thereof include a method of treating a textile product with a treatment liquid by a pad method, a dipping method, a spraying method, a foaming method, a coating method, and the like, and then drying. Further, after drying, a curing (heat treatment) step may be incorporated as necessary.
  • a drying method a conventionally used method can be used without limitation, and either a dry heat method or a wet heat method may be used.
  • the material of the textile product to which the manufacturing method according to this embodiment can be applied is not particularly limited, and natural fibers such as cotton, hemp, silk, and wool, semi-synthetic fibers such as rayon and acetate, nylon, polyester, polyurethane, and polypropylene. And synthetic fibers such as these, composite fibers of these, and blended fibers.
  • the form of the textile product may be any form such as a woven fabric, a knitted fabric, a yarn, a nonwoven fabric, and paper.
  • Example 1 In a 500 ml flask, 72 g of C 6 F 13 CH 2 CH 2 OC (O) C (CH 3 ) ⁇ CH 2 (hereinafter abbreviated as C6FMA) as the monomer (A) and isoform as the monomer (B) 18 g of bornyl methacrylate (hereinafter abbreviated as IBMA), 5 g of polyoxyethylene alkyl ether (hereinafter abbreviated as POA), 1 g of stearyltrimethylammonium chloride (hereinafter abbreviated as STMAC), 30 g of propylene glycol (hereinafter abbreviated as PPG), In addition, 261.7 g of ion-exchanged water was added and mixed with stirring at 40 ° C.
  • C6FMA C 6 F 13 CH 2 CH 2 OC (O) C (CH 3 ) ⁇ CH 2
  • IBMA bornyl methacrylate
  • POA polyoxyethylene alkyl ether
  • STMAC steary
  • the mixture was emulsified and dispersed with an ultrasonic emulsifier, cooled to 30 ° C. or lower, and transferred to a 300 ml stainless steel autoclave container. To this, 0.3 g of dodecyl mercaptan was added and nitrogen substitution was performed for 10 minutes. To this, 0.3 g of V-50 (manufactured by Wako Pure Chemical Industries) was added. Reaction was performed at 60 degreeC for 6 hours, and the water / oil repellent composition was obtained.
  • the obtained water / oil repellent composition had a non-volatile content of 30.8%.
  • the melt viscosity at 105 ° C. of the copolymer contained in the water / oil repellent composition was about 5800 Pa ⁇ s.
  • the melt viscosities of the copolymers obtained in Examples and Comparative Examples are obtained by adding an organic solvent such as methanol or acetone to the water / oil repellent composition and drying the solid content separated by emulsion breakage.
  • the sample was measured using a flow tester CFT-500D (manufactured by SHIMADZU) at a measurement temperature of 105 ° C.
  • this treatment liquid B a dyed polyester woven fabric (120 g / m 2 ) is immersed, and the wet pick-up rate is reduced to 60% with a mangle, followed by drying at 120 ° C. for 60 seconds and further at 180 ° C. for 30 seconds.
  • a water / oil repellent fiber product B was obtained.
  • the durable water repellency of this water / oil repellent fiber product B was evaluated by the method described below. The results are shown in Table 5.
  • Naphthalenesulfonic acid sodium salt is assumed to be a dye dispersant brought in from a processed cloth during water-repellent processing.
  • Examples 2 to 13, Comparative Examples 1 to 9 The same procedure as in Example 1 was performed except that the monomer (A), monomer (B), monomer (C), and other monomers were changed to the compositions shown in Tables 5 to 9.
  • the water / oil repellent compositions and water / oil repellent fiber products A to C of Examples 1 to 13 and Comparative Examples 1 to 9 were obtained, respectively.
  • C6FMA C 6 F 13 CH 2 CH 2 OC (O) C (CH 3)
  • IBMA isobornyl methacrylate
  • BzMA benzyl methacrylate
  • CHMA cyclohexyl methacrylate
  • VCM vinyl chloride monomer
  • VDC vinylidene chloride
  • HEMA hydroxyethyl methacrylate
  • SA stearyl acrylate
  • LA lauryl acrylate 2g / l, 4g / l and 6g / l Indicates the concentration of the water / oil repellent composition in the treatment liquid A, respectively.
  • a water and oil repellency component having a perfluoroalkyl group having 6 or less carbon atoms can be used to provide good water and oil repellency, durability, processing stability and texture.
  • An oil repellent composition and a method for producing a water / oil repellent fiber product using the composition can be provided.
  • the water / oil repellent composition of the present invention compared to the conventional water / oil repellent component having a perfluoroalkyl group having 6 or less carbon atoms, it has better water / oil repellency and its durability, processing stability and texture. Can be given to textile products and the like.

Abstract

L'invention concerne une composition hydrofuge et oléofuge contenant un copolymère qui est obtenu par copolymérisation d'une composition de monomères qui comprend un monomère (A) et un monomère (B) ou le monomère (A), le monomère (B) et un monomère (C). Le rapport de mélange (rapport en masse) du monomère (A) au monomère (B) est de 95:5 à 80:20 et le rapport de mélange (rapport en masse) du total du monomère (A) et du monomère (B) au monomère (C) est de 100:0 à 60:40. Le monomère (A) est au moins un monomère qui est représenté par la formule (1). Formule (1) : C6F13(CH2)nOC(O)C(R1)= CH2 (dans la formule (1), n vaut 2 ou 3 et R1 représente un atome d'hydrogène ou un groupe méthyle). Le monomère (B) est au moins un monomère choisi dans le groupe constitué par le (méth)acrylate d'isobornyle, le (méth)acrylate de cyclohexyle et le (méth)acrylate de benzyle. Le monomère (C) est au moins un monomère choisi dans le groupe constitué par les halogénures de vinyle, les halogénures de vinylidène, un (méth)acrylate polyoxyéthylénique et le vinylsilane.
PCT/JP2014/066474 2014-06-20 2014-06-20 Composition hydrofuge et oléofuge et procédé de production pour produit textile hydrofuge et oléofuge WO2015194049A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH713490A1 (de) * 2017-02-27 2018-08-31 Schoeller Tech Ag Zusammensetzung zur Imprägnierung von Holz- und Steinoberflächen.
WO2019124585A1 (fr) * 2017-12-21 2019-06-27 니카코리아(주) Composition d'agent d'apprêtage antisalissure et produit textile utilisant celle-ci

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JP2009102463A (ja) * 2007-10-22 2009-05-14 Yunimatekku Kk 撥水撥油剤
JP2011099077A (ja) * 2009-11-09 2011-05-19 Noda Screen:Kk フッ素系重合体およびコーティング剤
JP2013136668A (ja) * 2011-12-28 2013-07-11 Daikin Industries Ltd 含フッ素組成物および含フッ素重合体
WO2014007345A1 (fr) * 2012-07-06 2014-01-09 ダイキン工業株式会社 Tissu perméable à l'humidité et étanche à l'eau
WO2014030648A1 (fr) * 2012-08-21 2014-02-27 旭硝子株式会社 Copolymère fluoré, son procédé de production, composition hydrofuge et article

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009102463A (ja) * 2007-10-22 2009-05-14 Yunimatekku Kk 撥水撥油剤
JP2011099077A (ja) * 2009-11-09 2011-05-19 Noda Screen:Kk フッ素系重合体およびコーティング剤
JP2013136668A (ja) * 2011-12-28 2013-07-11 Daikin Industries Ltd 含フッ素組成物および含フッ素重合体
WO2014007345A1 (fr) * 2012-07-06 2014-01-09 ダイキン工業株式会社 Tissu perméable à l'humidité et étanche à l'eau
WO2014030648A1 (fr) * 2012-08-21 2014-02-27 旭硝子株式会社 Copolymère fluoré, son procédé de production, composition hydrofuge et article

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH713490A1 (de) * 2017-02-27 2018-08-31 Schoeller Tech Ag Zusammensetzung zur Imprägnierung von Holz- und Steinoberflächen.
WO2019124585A1 (fr) * 2017-12-21 2019-06-27 니카코리아(주) Composition d'agent d'apprêtage antisalissure et produit textile utilisant celle-ci

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