WO2023053735A1 - Polymère, procédé de production de polymère, composition hydrofuge et oléofuge, et article - Google Patents
Polymère, procédé de production de polymère, composition hydrofuge et oléofuge, et article Download PDFInfo
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- WO2023053735A1 WO2023053735A1 PCT/JP2022/030556 JP2022030556W WO2023053735A1 WO 2023053735 A1 WO2023053735 A1 WO 2023053735A1 JP 2022030556 W JP2022030556 W JP 2022030556W WO 2023053735 A1 WO2023053735 A1 WO 2023053735A1
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- Prior art keywords
- polymer
- monomer
- water
- unit
- polymerization
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- 229920000642 polymer Polymers 0.000 title claims abstract description 188
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 46
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 116
- 239000000178 monomer Substances 0.000 claims description 115
- 238000006116 polymerization reaction Methods 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 59
- 230000002940 repellent Effects 0.000 claims description 39
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000003505 polymerization initiator Substances 0.000 claims description 15
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 8
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- 238000000034 method Methods 0.000 description 29
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- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 6
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- FYQFWFHDPNXORA-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C FYQFWFHDPNXORA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
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- 238000004821 distillation Methods 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 238000005227 gel permeation chromatography Methods 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 3
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- LWMFAFLIWMPZSX-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene Chemical compound N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LWMFAFLIWMPZSX-UHFFFAOYSA-N 0.000 description 3
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YHOSNAAUPKDRMI-UHFFFAOYSA-N n,n-di(propan-2-yl)prop-2-enamide Chemical compound CC(C)N(C(C)C)C(=O)C=C YHOSNAAUPKDRMI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000013055 pulp slurry Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical class SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- a polymer has the following units (a) and the following units (b); and the proportion of said units (b) is 40 to 80 mol% of said total of said units (a) and said units (b).
- Unit (a) A unit represented by the following formula (1). —(CH 2 —CHR f )— (1) However, R f is a perfluoroalkyl group having 1 to 8 carbon atoms.
- Unit (b): A unit represented by the following formula (2). —(CH 2 —CH—(OC( O)NH—R d ))— (2) However, R d is an alkyl group having 6 to 24 carbon atoms.
- a “unit” is a generic term for an atomic group directly formed by polymerization of one molecule of a monomer and an atomic group obtained by chemically converting a part of the atomic group.
- a “unit based on a monomer” means an atomic group directly formed by polymerization of one molecule of a monomer.
- monomer is meant a compound having a polymerizable carbon-carbon double bond.
- (Meth)acrylate is a generic term for acrylate and methacrylate. The solid content concentration is calculated by solid content mass / sample mass ⁇ 100, where the mass of the sample before heating is the sample mass, and the mass after drying the sample for 4 hours in a 120 ° C.
- the present composition contains a methylol-based cross-linking agent or a glyoxal resin-based anti-wrinkle agent
- a catalyst as an additive.
- Preferred catalysts include, for example, inorganic amine salts and organic amine salts.
- Inorganic amine salts include, for example, ammonium chloride.
- Examples of organic amine salts include aminoalcohol hydrochloride and semicarbazide hydrochloride.
- Amino alcohol hydrochlorides include, for example, monoethanolamine hydrochloride, diethanolamine hydrochloride, triethanol hydrochloride, and 2-amino-2-methylpropanol hydrochloride.
- Example 9 6 g of the dispersion liquid obtained in Polymerization Example 4 was added dropwise to 60 g of a mixed liquid of 6 g of hexane and 54 g of 2-butanol, and stirred to precipitate a solid. The resulting solid was then separated after centrifugation at 3000 rpm for 5 minutes. To the separated solid, 30 g of isopropyl alcohol-denatured alcohol (manufactured by Imazu, product name: 95% IPA-denatured alcohol) and 30 g of ion-exchanged water were added and thoroughly stirred. After centrifuging at 3000 rpm for 5 minutes, the solid obtained by removing the supernatant was vacuum-dried overnight at 35° C. to obtain a polymer (A4). The obtained polymer (A4) was dissolved in MIBK so that the solid content concentration was 1% by mass, to prepare the MIBK solution of Example 9.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
La présente invention concerne : un polymère qui permet la production d'un article ayant un excellent caractère hydrofuge et oléofuge ; un procédé de production du polymère ; une composition hydrofuge et oléofuge comprenant le polymère ; et un article ayant un excellent caractère hydrofuge et oléofuge. Le polymère selon la présente invention comprend une unité (a) représentée par la formule (1) et une unité (b) représentée par la formule (2), la proportion de l'unité (a) par rapport au total de l'unité (a) et de l'unité (b) étant de 20 à 60 % en moles ; et la proportion de l'unité (b) par rapport au total de l'unité (a) et de l'unité (b) étant de 40 à 80 % en moles. Formule (1) : -(CH2-CHRf)- ; Formule (2) : -(CH2-CH-(O-C(=O)NH-Rd))-, Rf étant un groupe perfluoroalkyle ayant 1 à 8 atomes de carbone, et Rd étant un groupe alkyle ayant de 6 à 24 atomes de carbone.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021159679 | 2021-09-29 | ||
| JP2021-159679 | 2021-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2023053735A1 true WO2023053735A1 (fr) | 2023-04-06 |
Family
ID=85782311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2022/030556 WO2023053735A1 (fr) | 2021-09-29 | 2022-08-10 | Polymère, procédé de production de polymère, composition hydrofuge et oléofuge, et article |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2023053735A1 (fr) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01123878A (ja) * | 1987-11-07 | 1989-05-16 | Nitto Denko Corp | 剥離剤及びその製造方法 |
| JPH07173772A (ja) * | 1993-12-21 | 1995-07-11 | Asahi Glass Co Ltd | 水分散型フッ素系撥水撥油剤およびその製造方法 |
| JPH09221619A (ja) * | 1996-02-19 | 1997-08-26 | Toyo Ink Mfg Co Ltd | 撥水コーティング用樹脂組成物 |
| JP2002129031A (ja) * | 2000-10-30 | 2002-05-09 | Nitto Denko Corp | ポリマー水分散体およびその製造方法 |
| WO2019216117A1 (fr) * | 2018-05-11 | 2019-11-14 | ダイキン工業株式会社 | Agent hydrofuge et oléofuge et produit textile |
-
2022
- 2022-08-10 WO PCT/JP2022/030556 patent/WO2023053735A1/fr active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01123878A (ja) * | 1987-11-07 | 1989-05-16 | Nitto Denko Corp | 剥離剤及びその製造方法 |
| JPH07173772A (ja) * | 1993-12-21 | 1995-07-11 | Asahi Glass Co Ltd | 水分散型フッ素系撥水撥油剤およびその製造方法 |
| JPH09221619A (ja) * | 1996-02-19 | 1997-08-26 | Toyo Ink Mfg Co Ltd | 撥水コーティング用樹脂組成物 |
| JP2002129031A (ja) * | 2000-10-30 | 2002-05-09 | Nitto Denko Corp | ポリマー水分散体およびその製造方法 |
| WO2019216117A1 (fr) * | 2018-05-11 | 2019-11-14 | ダイキン工業株式会社 | Agent hydrofuge et oléofuge et produit textile |
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