CN113993916A - Coating agent and article treated with the coating agent - Google Patents
Coating agent and article treated with the coating agent Download PDFInfo
- Publication number
- CN113993916A CN113993916A CN202080043999.1A CN202080043999A CN113993916A CN 113993916 A CN113993916 A CN 113993916A CN 202080043999 A CN202080043999 A CN 202080043999A CN 113993916 A CN113993916 A CN 113993916A
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- China
- Prior art keywords
- meth
- acrylate compound
- coating agent
- acrylate
- mass
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims abstract description 68
- -1 acrylate compound Chemical class 0.000 claims abstract description 135
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 28
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 239000000470 constituent Substances 0.000 claims abstract description 26
- 229920001577 copolymer Polymers 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims description 18
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 32
- 238000000034 method Methods 0.000 abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
- 239000010985 leather Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- XVTQAXXMUNXFMU-UHFFFAOYSA-N methyl 2-(3-oxo-2-pyridin-2-yl-1h-pyrazol-5-yl)acetate Chemical compound N1C(CC(=O)OC)=CC(=O)N1C1=CC=CC=N1 XVTQAXXMUNXFMU-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 239000004575 stone Substances 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 238000007611 bar coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- STYXVTBFUKQEKM-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F STYXVTBFUKQEKM-UHFFFAOYSA-N 0.000 description 2
- LZEFLPFLUMQUPG-UHFFFAOYSA-N 1-(2-hydroxyethoxy)-2-methylbutan-2-ol Chemical compound CC(COCCO)(CC)O LZEFLPFLUMQUPG-UHFFFAOYSA-N 0.000 description 2
- LIRNFNXOTBZTPP-UHFFFAOYSA-N 1-[2-(2-hydroxyethoxy)ethoxy]-2-methylpropan-2-ol Chemical compound CC(C)(O)COCCOCCO LIRNFNXOTBZTPP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- UAZLJXALDUIFJV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol 2-methylbut-2-ene Chemical compound CC(=CC)C.C(COCCO)O UAZLJXALDUIFJV-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- ZBZICERRZIMWGX-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,6-tridecafluorohexan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZBZICERRZIMWGX-UHFFFAOYSA-N 0.000 description 1
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 description 1
- QMGJMGFZLXYHCR-UHFFFAOYSA-N 1-(2-butoxypropoxy)butane Chemical compound CCCCOCC(C)OCCCC QMGJMGFZLXYHCR-UHFFFAOYSA-N 0.000 description 1
- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- IEMBFTKNPXENSE-UHFFFAOYSA-N 2-(2-methylpentan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCCC(C)(C)OOC(C)(C)OC(O)=O IEMBFTKNPXENSE-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- VPKQPPJQTZJZDB-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOC(=O)C=C VPKQPPJQTZJZDB-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000005817 fluorobutyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
The present invention provides a technique for imparting excellent water repellency and oil repellency and excellent slipping property. The coating agent is a coating agent containing a copolymer formed by polymerizing a constituent monomer containing: the coating agent comprises a (meth) acrylate compound (A) having a fluoroalkyl group having 1 to 6 carbon atoms, a (meth) acrylate compound (B1) having an aromatic ring, and an alicyclic (meth) acrylate compound (B2), wherein the total amount of the (meth) acrylate compound (A), the (meth) acrylate compound (B1) having an aromatic ring, and the alicyclic (meth) acrylate compound (B2) is 90 mass% or more of the total amount of the constituent monomers.
Description
Technical Field
The present invention relates to a coating agent and an article treated with the coating agent.
Background
Conventionally, as a coating agent for imparting water repellency and oil repellency by coating the surface of a fiber product, a leather product, or the like, a coating agent containing a fluorine-based polymer having a fluoroalkyl group having 8 or more carbon atoms has been known. However, when a fluorine-based polymer having a fluoroalkyl group having 8 or more carbon atoms is decomposed, perfluorooctanoic acid may be generated, which may be accumulated in a living body. Therefore, development of an alternative to fluorine-based polymers having a fluoroalkyl group having 8 or more carbon atoms is desired.
Patent document 1 describes a technique related to an alternative to a fluorine-based polymer having a fluoroalkyl group having 8 or more carbon atoms. Specifically, patent document 1 describes a coating agent containing a polymer obtained by polymerizing (i) a monomer having a perfluoroalkyl group having 6 or less carbon atoms and (ii) at least one of cyclohexyl (meth) acrylate and isobornyl (meth) acrylate.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2011-99077
Disclosure of Invention
Technical problem to be solved by the invention
Indeed, the coating agent described in patent document 1 can impart water repellency and oil repellency by being applied to the surface of a textile product, a leather product, or the like. However, the present inventors have found that the coating agent described in patent document 1 cannot provide slip properties, and therefore has a problem that it is difficult to remove droplets when they adhere to a portion to which the coating agent is applied. Therefore, it is desired to develop a technology relating to a coating agent which imparts excellent water repellency and oil repellency and which imparts excellent slipping property.
Means for solving the problems
The present invention has been made to solve the above problems, and can be realized as follows.
(1) According to one embodiment of the present invention, a coating agent is provided. The coating agent contains a copolymer formed by polymerizing a constituent monomer, the constituent monomer including:
a (meth) acrylate compound (A) having a fluoroalkyl group having 1 to 6 carbon atoms;
a (meth) acrylate compound having an aromatic ring (B1); and
an alicyclic (meth) acrylate compound (B2), wherein, in the coating agent,
the total blending amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is 90 mass% or more of the total blending amount of the constituent monomers.
According to the coating agent of this embodiment, excellent water repellency and oil repellency can be imparted, and excellent slipping property can be imparted.
(2) In the coating agent of the above aspect, the alicyclic (meth) acrylate compound (B2) includes any one functional group of an isobornyl group, a dicyclopentyl group, a dicyclopentenyl group, and an adamantyl group.
According to the coating agent of this embodiment, excellent water repellency and oil repellency can be imparted, and further excellent slipping property can be imparted.
(3) In the coating agent of the above-described embodiment, the alicyclic (meth) acrylate compound (B2) may contain an isobornyl group.
According to the coating agent of this embodiment, excellent water repellency and oil repellency can be imparted, and further excellent slipping property can be imparted.
(4) In the coating agent of the above aspect, the (meth) acrylate compound having an aromatic ring (B1) may include a benzyl group.
According to the coating agent of this embodiment, excellent water repellency and oil repellency can be imparted, and further excellent slipping property can be imparted.
The present invention can be realized in various forms, for example, in the form of an article treated with a coating agent.
Detailed Description
A. Coating agent
A coating agent according to an embodiment of the present invention contains a copolymer obtained by polymerizing a constituent monomer including: (i) a (meth) acrylate compound (A) having a fluoroalkyl group having 1 to 6 carbon atoms, (ii) a (meth) acrylate compound (B1) having an aromatic ring, and (iii) an alicyclic (meth) acrylate compound (B2). The total blending amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is 90 mass% or more of the total blending amount of the constituent monomers. In the present specification, "(meth) acrylate" means acrylate or methacrylate. In the present specification, the term "constituent monomer" refers to a monomer constituting a copolymer.
According to the coating agent of the present embodiment, excellent water repellency and oil repellency can be provided, and excellent slipping property can be provided. Here, the slipperiness indicates whether or not a droplet of water or the like attached to the surface of the substrate is likely to move due to the gravity received by the inclination of the surface of the substrate. In the present specification, it is shown that the more easily the droplet moves due to the gravity received by the inclination of the substrate surface, the more excellent the slipping property. Hereinafter, the constituent monomers of the coating agent of the present embodiment will be described.
(meth) acrylate Compound (A) >, and
the (meth) acrylate compound (A) of the present embodiment has a fluoroalkyl group having 1 to 6 carbon atoms. Examples of the (meth) acrylate compound (a) include: fluoroalkyl (meth) acrylate, fluoroalkyl alkyl (meth) acrylate, fluoroalkyl polyoxyalkylene (meth) acrylate, and the like. Of these, in order to obtain excellent water repellency, oil repellency, and slipping property, fluoroalkyl (meth) acrylate and fluoroalkyl (meth) acrylate are preferable, and fluoroalkyl (meth) acrylate is more preferable. The fluoroalkyl group is preferably a fluoroalkyl group having 2 to 6 carbon atoms, more preferably a fluoroalkyl group having 4 to 6 carbon atoms, and further preferably a fluoroalkyl group having 6 carbon atoms, in order to have excellent water repellency, oil repellency, and slipping property. Here, in the present specification, "fluorine" includes perfluoro. The fluoroalkyl group is preferably a perfluoroalkyl group.
Examples of the fluoroalkyl (meth) acrylate include: fluoromethyl (meth) acrylate, fluoroethyl (meth) acrylate, fluoropropyl (meth) acrylate, fluorobutyl (meth) acrylate, fluoropentyl (meth) acrylate, fluorohexyl (meth) acrylate, and the like.
Here, the fluoroalkyl (meth) acrylate may be represented by the following general formula (1).
Rf-O-X (1)
Wherein Rf is fluoroalkyl, and X is acryloyl or methacryloyl.
Examples of fluoroalkyl alkyl (meth) acrylates include: fluoromethyl methyl (meth) acrylate, fluoromethyl ethyl (meth) acrylate, fluoroethyl methyl (meth) acrylate, fluoroethyl ethyl (meth) acrylate, fluoropropyl methyl (meth) acrylate, fluoropropyl ethyl (meth) acrylate, fluorobutyl methyl (meth) acrylate, fluorobutyl ethyl (meth) acrylate, fluoropentyl methyl (meth) acrylate, fluoropentyl ethyl (meth) acrylate, fluorohexyl methyl (meth) acrylate, fluorohexyl ethyl (meth) acrylate, and the like. The fluoroalkyl alkyl (meth) acrylate may be represented by the following general formula (2).
Rf-Y-O-X (2)
Wherein Rf is fluoroalkyl, Y is alkylene, and X is acryloyl or methacryloyl.
Examples of the fluoroalkyl polyoxyalkylene (meth) acrylate include: fluoromethylpolyoxyfluoroethylene (meth) acrylate, fluoroethylpolyoxyfluoroethylene (meth) acrylate, fluoropropylpolyethyleneoxyfluoroethylene (meth) acrylate, fluorobutylpolyethyleneoxyfluoroethylene (meth) acrylate, fluoropentylpolyoxyfluoroethylene (meth) acrylate, fluorohexylpolyethyleneoxyfluoride (meth) acrylate, fluorohexylpolypropyleneoxide (meth) acrylate, and the like. The fluoroalkyl polyoxyalkylene (meth) acrylate may be represented by the following general formula (3).
Rf-Z-O-X (3)
Wherein Rf is fluoroalkyl, Z is polyoxyfluoroalkylene, and X is acryloyl or methacryloyl.
The (meth) acrylate compound (a) is preferably perfluorohexylethyl (meth) acrylate, and particularly preferably perfluorohexylethyl methacrylate, in order to obtain excellent water repellency, oil repellency and slipping property.
< meth (acrylate) Compound (B1) having an aromatic Ring
Examples of the (meth) acrylate compound having an aromatic ring (B1) in the present embodiment include: a (meth) acrylate compound having a benzyl group, a (meth) acrylate compound having a phenoxy group, and the like. The (meth) acrylate compound having an aromatic ring (B1) is preferably a (meth) acrylate compound having a benzyl group in order to have excellent water repellency, oil repellency, and slipping property.
More specifically, the (meth) acrylate compound having an aromatic ring (B1) in the present embodiment includes, for example: benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, and the like. The (meth) acrylate compound having an aromatic ring (B1) is preferably benzyl (meth) acrylate, and particularly preferably benzyl methacrylate, in order to achieve excellent water repellency, oil repellency, and slipping property.
< alicyclic (meth) acrylate Compound (B2) >
Examples of the alicyclic (meth) acrylate compound (B2) in the present embodiment include: a (meth) acrylate compound having an isobornyl group, a (meth) acrylate compound having a dicyclopentyl group, a (meth) acrylate compound having a dicyclopentenyl group, a (meth) acrylate compound having an adamantyl group, and the like. The alicyclic (meth) acrylate compound (B2) is preferably a (meth) acrylate compound having an isobornyl group in order to have excellent water repellency, oil repellency, and slipping property.
More specifically, the alicyclic (meth) acrylate compound (B2) includes, for example: cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, 1-adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and the like. The alicyclic (meth) acrylate compound (B2) is preferably isobornyl (meth) acrylate, 1-adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, or dicyclopentenyl (meth) acrylate, and particularly preferably isobornyl (meth) acrylate, in order to obtain excellent water repellency, oil repellency, and slipping property.
The constituent monomers constituting the copolymer of the present embodiment may include monomers other than the component (a), the component (B1), and the component (B2) within a range not departing from the object of the invention. Similarly, the coating agent of the present embodiment may contain a copolymer other than the above-described copolymer within a range not departing from the object of the invention.
In the present embodiment, the total blending amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is 90 mass% or more of the total blending amount of the constituent monomers. The total blending amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is preferably 92 mass% or more, and more preferably 95 mass% or more of the total blending amount of the constituent monomers, from the viewpoint of excellent slipping property. The total amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is 100 mass% or less of the total amount of the constituent monomers.
In order to have excellent slipping properties, the amount of the (meth) acrylate compound (a) is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, and particularly preferably 55% by mass or more, based on the total amount of the constituent monomers. On the other hand, the amount of the (meth) acrylate compound (a) to be blended is preferably 95% by mass or less, more preferably 90% by mass or less, still more preferably 87% by mass or less, and particularly preferably 85% by mass or less, based on the total blending amount of the constituent monomers. Therefore, for example, the amount of the (meth) acrylate compound (a) to be blended may be 80% by mass based on the total blending amount of the constituent monomers.
The amount of the (meth) acrylate compound having an aromatic ring (B1) blended is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 13% by mass or more, and particularly preferably 15% by mass or more, relative to the total blending amount of the constituent monomers. On the other hand, the amount of the (meth) acrylate compound having an aromatic ring (B1) blended is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, and particularly preferably 25% by mass or less, relative to the total blending amount of the constituent monomers.
The amount of the alicyclic (meth) acrylate compound (B2) is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 13% by mass or more, and particularly preferably 15% by mass or more, based on the total amount of the constituent monomers. On the other hand, the amount of the alicyclic (meth) acrylate compound (B2) is preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, and particularly preferably 25% by mass or less, relative to the total amount of the constituent monomers.
In order to have excellent slipping properties, the ratio ((B2)/(B1)) of the amount of the alicyclic (meth) acrylate compound (B2) to the amount of the (meth) acrylate compound having an aromatic ring (B1) is preferably 10 or less, more preferably 8 or less, still more preferably 6 or less, particularly preferably 4 or less, and still more preferably 1.5 or less. The ratio ((B2)/(B1)) of the amount of the alicyclic (meth) acrylate compound (B2) blended to the amount of the (meth) acrylate compound having an aromatic ring (B1) blended is preferably 0.5 or more, more preferably 0.7 or more, and still more preferably 1 or more.
The solvent used in the present embodiment is not particularly limited, and may be, for example, an organic solvent. Examples of the organic solvent include: aromatic solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as hexane; alicyclic hydrocarbon solvents such as cyclohexane and isophorone; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and propylene glycol diacetate; glycol ether ester solvents such as ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, dipropylene glycol methyl ether acetate, diethylene glycol monoethyl ether acetate, and 3-methoxy-3-methylbutyl acetate; glycol ether solvents such as ethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol dibutyl ether, dimethyltriethylene glycol (dimethyltriethylene glycol), methylethyl diethylene glycol, and dimethylpropylene diethylene glycol; dimethyl sulfoxide, dimethylformamide, N-methyl-2-pyrrolidone, etc., and among them, acetone, methyl ethyl ketone, ethyl acetate, ethylene glycol dimethyl ether, diethylene glycol diethyl ether, methyl ethyl diethylene glycol, propylene glycol monomethyl ether acetate, 3-methoxy-3-methylbutyl acetate, and dimethylpropylene diethylene glycol are preferable.
Next, a method for producing the coating agent of the present embodiment will be described. The method for producing the coating agent is not particularly limited. For example, the following methods can be mentioned: a method for producing a copolymer, which comprises mixing a (meth) acrylate compound (A) having a fluoroalkyl group having 1 to 6 carbon atoms, a (meth) acrylate compound (B1) having an aromatic ring, an alicyclic (meth) acrylate compound (B2), and a solvent, and heating the mixture.
The polymerization method is not particularly limited, and solution polymerization is preferable. The polymerization temperature is not particularly limited, but is preferably in the range of 40 ℃ to 120 ℃. The polymerization time is not particularly limited, but is preferably about 4 to 15 hours.
A polymerization initiator may be used for the polymerization. The polymerization initiator is not particularly limited, and examples thereof include: peroxides such as benzoyl peroxide, t-butyl peroxypivalate, t-butyl peroxy-2-ethylhexanoate, t-hexylperoxyisopropyl monocarbonate, and 1,1,3, 3-tetramethylbutylperoxy-2-ethylhexanoate; azo compounds such as azobisisobutyronitrile and 2,2' -azobis-2-methylbutyronitrile. The amount of the polymerization initiator used is not particularly limited, and is preferably 0.1 to 5 parts by mass per 100 parts by mass of the constituent monomers.
The coating agent of the present embodiment may further contain, for example, other hydrophilic agents, other oil-repellent agents, water-repellent agents, insect-repellent agents, flame retardants, wrinkle-preventing agents, antistatic agents, softening agents, preservatives, fragrances, antioxidants, emulsifiers, dispersants, resin additives, and the like, as long as the object of the invention is not violated.
The coating agent of the present embodiment can be used as a coating agent for various articles including glass, plastic, metal, electronic substrates, textile products, leather, stone, wood, paper, and the like. The coating agent of the present embodiment can be used more specifically, for example, for the body of an automobile and the glass of an automobile; walls of buildings, glass of buildings, roofs of buildings; an umbrella; electronic devices and electronic parts such as smart phones, personal computers, portable radios, digital recorders, printed circuit boards, and the like; a bearing of the motor; metal parts such as a handlebar of a bicycle and a frame of the bicycle; various metals; tents and tarpaulins for outdoor articles; carpets, curtains, bags; leather, stone, wood, paper, etc. A method of appropriately selecting a coating method such as spray coating, spin coating, or dipping depending on the object article, and drying or crosslinking the coating by heat treatment as necessary can be used.
The coating agent of the present embodiment can be used, for example, as a chemical-resistant coating agent for protecting a substrate from saline water, an electrolytic solution, a corrosive gas, or the like, or as a raw liquid for water mist prevention. The coating agent of the present embodiment can be added to a coating material to function as a coating agent.
The coating agent of the present embodiment may be dissolved and mixed with various resins using various solvents to function as a coating agent. The resin is not particularly limited, and examples thereof include: acrylic resin, urethane resin, acrylic silicone resin, epoxy resin, vinyl resin, silicone resin, and the like. Among them, acrylic resins are preferable.
The resin content in the coating agent of the present embodiment is not particularly limited. The resin content in the coating agent of the present embodiment is preferably 1% by mass or more, more preferably 3% by mass or more, and further preferably 5% by mass or more. On the other hand, the resin content in the coating agent of the present embodiment is preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less.
The content of the copolymer in the coating agent of the present embodiment is not particularly limited. The content of the copolymer in the coating agent of the present embodiment is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, further preferably 0.1% by mass or more, particularly preferably 0.5% by mass or more, and further preferably 1% by mass or more in terms of solid content. On the other hand, the content of the copolymer in the coating agent of the present embodiment is preferably 50% by mass or less, more preferably 30% by mass or less, further preferably 20% by mass or less, particularly preferably 10% by mass or less, and further preferably 7% by mass or less.
B. Article treated with coating agent
Another embodiment of the present invention is an article treated with the coating agent. The treatment method is not particularly limited, and examples thereof include: coating, spraying, dipping, and the like. The treatment method may be appropriately selected depending on each article. The article is not particularly limited, and examples thereof include glass, plastic, metal, electronic substrates, fiber products, leather, stone, wood, paper, and the like. More specifically, the article includes, for example: automobile bodies, automobile glass; walls of buildings, glass of buildings, roofs of buildings; an umbrella; electronic devices and electronic parts such as smart phones, personal computers, portable radios, digital recorders, printed circuit boards, and the like; a bearing of the motor; metal parts such as a handlebar of a bicycle and a frame of the bicycle; various metals; tents and tarpaulins for outdoor articles; carpets, curtains, bags; leather, stone, wood, paper, etc.
Examples
The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to the following examples.
(use of raw materials)
A (meth) acrylate compound (A) having a fluoroalkyl group having 1 to 6 carbon atoms
(A-1) Perfluorohexylethyl methacrylate
(A-2) Perfluorobutyl Ethyl methacrylate
(A-3) Perfluorohexylethyl acrylate
(meth) acrylate Compound having aromatic Ring (B1)
(B1) Methacrylic acid benzyl ester
Alicyclic (meth) acrylate Compound (B2)
(B2-1) isobornyl acrylate
(B2-2) isobornyl methacrylate
(B2-3) Cyclohexylacrylate
Constituent monomers other than (A1), (B1) and (B2)
(C-1) stearyl methacrylate
Solvent(s)
(D-1) 3-methoxy-3-methylbutyl acetate (SOLFITAC, manufactured by Coli Ltd.)
(D-2) ethylene glycol dimethyl Ether (DMG)
(D-3) Methyl Ethyl Ketone (MEK)
(D-4) Propylene Glycol Methyl Ether Acetate (PGMEA)
(D-5) diethylene glycol Diethyl Ether (DEDG)
(D-6) Ethyl acetate
(example 1)
In a reaction vessel equipped with a stirrer, a thermometer, a nitrogen introduction pipe and a reflux pipe, 300 parts of the compounds of (a), (B1) and (B2) and 3-methoxy-3-methylbutylacetate as a solvent were added at the mass ratio described in table 1 below, and nitrogen substitution was performed. Then, tert-butyl peroxypivalate (trade name: PERBUTYL (registered trademark) PV, manufactured by Nichikoku corporation) was added in an amount of 3 parts by mass based on 100 parts by mass of the total amount of the compounds (A), (B1) and (B2), and the mixture was reacted at 65 ℃ for 8 hours, followed by distilling off the solvent to obtain a copolymer solution (solid content of copolymer: 25% by mass).
(examples and comparative examples other than example 1)
In examples and comparative examples other than example 1, copolymer solutions were obtained in the same manner as in example 1, using the materials and mass ratios described in tables 1 to 2, which will be described later.
Using the prepared copolymer solution, the following tests 1 and 2 were performed. Specifically, the following properties were evaluated.
(test 1)
Ethyl acetate was added to the obtained copolymer solution, and dilution was performed so that the concentration of the copolymer was 1 mass%, thereby obtaining a treatment liquid a. A slide glass plate (75 mm. times.25 mm, thickness 1mm) manufactured by AS ONE was coated by a bar coating method so that the thickness of the treatment liquid A was 10 μm. Then, the treatment liquid was dried in an oven at 105 ℃ for 10 minutes to prepare a test piece for evaluating water repellency and oil repellency.
Further, ethyl acetate was added to the obtained copolymer solution, and the mixture was diluted so that the concentration of the copolymer was 25 mass%, thereby obtaining a treatment liquid B. After wiping a slide glass (a standard large-sized frosted side t1.3 slide glass (76 mm. times.52 mm, thickness 1mm) manufactured by Sonlang Nitri industries, Ltd.) with a thin paper soaked with 1ml of 99.5 mass% ethanol (manufactured by NACALI TESSQUE Co., Ltd.), degreasing was performed, the slide glass was dried at 25 ℃ for 10 minutes. The slide glass plate after completion of degreasing was coated by a bar coating method so that the thickness of the treatment solution B was 10 μm. Then, the treatment liquid B was dried in an oven at 150 ℃ for 10 minutes to prepare a test piece for evaluating the slipping property.
(test 2)
A coating agent was prepared by mixing 0.5 parts by mass of an obtained copolymer solution, 0.5 parts by mass of polymethyl methacrylate (having an average polymerization degree of about 8000, manufactured by NACALALI TESSQUE Co., Ltd.) and 10 parts by mass of ethyl acetate in terms of the solid content of the copolymer, and heating and dissolving the mixture at 70 ℃. The coating agent was applied onto a glass plate by a bar coating method so that the thickness of the coating agent was 10 μm. Then, the coating agent was dried in an oven at 80 ℃ for 10 minutes to prepare a test piece for evaluating water repellency, oil repellency, and slipping property.
(method of evaluating Water repellency and oil repellency)
The water repellency and oil repellency were evaluated by using a contact angle measuring device (Drop Master 500, manufactured by synechia scientific corporation). Specifically, the water repellency was evaluated by measuring the contact angle of water on the coated surface, and the oil repellency was evaluated by measuring the contact angle of hexadecane on the coated surface. The water repellency was a water contact angle and the oil repellency was a hexadecane contact angle, and the evaluation was made according to each standard. The droplet volume of water was 2. mu.L, and the droplet volume of hexadecane was 4. mu.L. Each evaluation was performed by measuring the contact angle 5 seconds after dropping.
The water repellency was evaluated on the following 5 scales. The larger the contact angle, the more excellent the water repellency, and thus is preferable.
A: the contact angle is more than 110 degrees
B: the contact angle is more than 100 DEG and less than 110 DEG
C: the contact angle is more than 90 DEG and less than 100 DEG
D: the contact angle is more than 70 degrees and less than 90 degrees
E: contact angle less than 70 °
The oil repellency was evaluated on the following 5 scales. The larger the contact angle, the more excellent the oil repellency, and therefore, the more preferable.
A: the contact angle is more than 60 degrees
B: the contact angle is more than 50 DEG and less than 60 DEG
C: the contact angle is more than 40 degrees and less than 50 degrees
D: the contact angle is more than 30 DEG and less than 40 DEG
E: contact angle less than 30 °
(method of evaluating slipperiness)
The evaluation of the slipping property was performed using a contact angle measuring apparatus (Drop Master 500, manufactured by synechia interface science corporation). Specifically, 20. mu.L of water was dropped onto the coating surface inclined at a predetermined angle, and the angle of slipping was defined as the slip angle. Based on the landing angle, evaluation was performed on the following 5 grades. The smaller the slip angle, the more excellent the slip property is, and therefore, the preferable.
A: slide off at 25 °
B: slide down at 30 DEG
C: slide off at 40 °
D: slide down at 50 °
E: does not slide off at 60 DEG
[ Table 1]
[ Table 2]
The following results are shown in tables 1 and 2. That is, it is found that examples 1 to 17 including the (meth) acrylate compound (B1) having an aromatic ring are superior to comparative examples 1 to 5 including no (meth) acrylate compound (B1) having an aromatic ring in both oil repellency and slipping property.
In addition, examples 1 to 17 in which the total blending amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is 90 mass% or more of the total blending amount of the constituent monomers are superior in slipping property to comparative example 6 in which the value is less than 90 mass%.
From the results of examples 13 to 17, it is clear that coating agents excellent in water repellency, oil repellency, and slipping property can be produced using various solvents.
Further, it is understood from comparison of examples 6 to 8 that in the (meth) acrylate compound (a), the use of perfluorohexylethyl (meth) acrylate is particularly superior in slipping property to the use of perfluorobutylethyl methacrylate.
Further, although not shown in the evaluation results, it is clear from the experimental results that example 6 is particularly excellent in the slipping property and example 11 is particularly excellent in the oil repellency.
The present invention is not limited to the above-described embodiments, and can be realized in various configurations without departing from the scope of the invention. For example, in order to solve part or all of the problems or to achieve part or all of the effects, the technical features in the embodiments and examples corresponding to the technical features in the respective aspects described in the section of the summary of the invention may be replaced or combined as appropriate. In addition, if a technical feature is not described as an essential technical feature in the present specification, it can be deleted as appropriate.
Claims (5)
1. A coating agent characterized by containing, as a main component,
the coating agent contains a copolymer formed by polymerizing a constituent monomer, the constituent monomer including:
a (meth) acrylate compound (A) having a fluoroalkyl group having 1 to 6 carbon atoms;
a (meth) acrylate compound having an aromatic ring (B1); and
an alicyclic (meth) acrylate compound (B2) wherein,
the total blending amount of the (meth) acrylate compound (a), the (meth) acrylate compound having an aromatic ring (B1), and the alicyclic (meth) acrylate compound (B2) is 90 mass% or more of the total blending amount of the constituent monomers.
2. The coating agent according to claim 1, wherein,
the alicyclic (meth) acrylate compound (B2) contains any one functional group selected from isobornyl, dicyclopentyl, dicyclopentenyl, and adamantyl.
3. The coating agent according to claim 1, wherein,
the alicyclic (meth) acrylate compound (B2) contains an isobornyl group.
4. The coating agent according to any one of claims 1 to 3, wherein,
the (meth) acrylate compound having an aromatic ring (B1) contains a benzyl group.
5. An article treated with the coating agent according to any one of claims 1 to 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-115591 | 2019-06-21 | ||
| JP2019115591A JP2021001271A (en) | 2019-06-21 | 2019-06-21 | Coating agent and article |
| PCT/JP2020/022454 WO2020255763A1 (en) | 2019-06-21 | 2020-06-08 | Coating agent and article treated with said coating agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113993916A true CN113993916A (en) | 2022-01-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080043999.1A Withdrawn CN113993916A (en) | 2019-06-21 | 2020-06-08 | Coating agent and article treated with the coating agent |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2021001271A (en) |
| KR (1) | KR20220023755A (en) |
| CN (1) | CN113993916A (en) |
| TW (1) | TW202100585A (en) |
| WO (1) | WO2020255763A1 (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5320266B2 (en) * | 2009-11-09 | 2013-10-23 | 株式会社野田スクリーン | Fluoropolymer and coating agent |
| JP6266287B2 (en) * | 2013-09-27 | 2018-01-24 | 第一工業製薬株式会社 | Polymer composition and water / oil repellent |
| JP5760210B2 (en) * | 2014-01-27 | 2015-08-05 | 株式会社野田スクリーン | Coating agent and method for forming coating film |
| JP6948248B2 (en) * | 2017-12-22 | 2021-10-13 | 第一工業製薬株式会社 | Copolymers, water and oil repellents and coating agents |
-
2019
- 2019-06-21 JP JP2019115591A patent/JP2021001271A/en active Pending
-
2020
- 2020-05-28 TW TW109117750A patent/TW202100585A/en unknown
- 2020-06-08 CN CN202080043999.1A patent/CN113993916A/en not_active Withdrawn
- 2020-06-08 KR KR1020217037917A patent/KR20220023755A/en unknown
- 2020-06-08 WO PCT/JP2020/022454 patent/WO2020255763A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| JP2021001271A (en) | 2021-01-07 |
| TW202100585A (en) | 2021-01-01 |
| WO2020255763A1 (en) | 2020-12-24 |
| KR20220023755A (en) | 2022-03-02 |
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