JP2022178714A - Composition for coating containing (poly)glycerol monomer - Google Patents
Composition for coating containing (poly)glycerol monomer Download PDFInfo
- Publication number
- JP2022178714A JP2022178714A JP2021085696A JP2021085696A JP2022178714A JP 2022178714 A JP2022178714 A JP 2022178714A JP 2021085696 A JP2021085696 A JP 2021085696A JP 2021085696 A JP2021085696 A JP 2021085696A JP 2022178714 A JP2022178714 A JP 2022178714A
- Authority
- JP
- Japan
- Prior art keywords
- group
- poly
- glycerin
- coating composition
- reactive functional
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 239000011248 coating agent Substances 0.000 title claims abstract description 26
- 238000000576 coating method Methods 0.000 title claims abstract description 25
- 239000000178 monomer Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims abstract description 9
- 125000000524 functional group Chemical group 0.000 claims abstract description 25
- 239000005871 repellent Substances 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- 235000011187 glycerol Nutrition 0.000 claims description 32
- 239000008199 coating composition Substances 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000002314 glycerols Chemical class 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 1
- 239000011521 glass Substances 0.000 abstract description 8
- 239000000758 substrate Substances 0.000 abstract description 5
- 229920003023 plastic Polymers 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 4
- 230000002459 sustained effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000010408 film Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- -1 vinyloxy group Chemical group 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- 229920000223 polyglycerol Polymers 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- MIJOCHWITRUYLZ-UHFFFAOYSA-N 1,1-dimethoxyethyl N-benzylcarbamate Chemical class COC(OC(NCC1=CC=CC=C1)=O)(C)OC MIJOCHWITRUYLZ-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- DOVZUKKPYKRVIK-UHFFFAOYSA-N 1-methoxypropan-2-yl propanoate Chemical compound CCC(=O)OC(C)COC DOVZUKKPYKRVIK-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- YAAYJRKCGZQWCB-UHFFFAOYSA-N 2-(1-cyanopropyldiazenyl)butanenitrile Chemical compound CCC(C#N)N=NC(CC)C#N YAAYJRKCGZQWCB-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- FLVSDXZOBZUNOB-UHFFFAOYSA-N 2-amino-1,3-diphenylpropan-1-one Chemical class C=1C=CC=CC=1C(=O)C(N)CC1=CC=CC=C1 FLVSDXZOBZUNOB-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- NMUBRRLYMADSGF-UHFFFAOYSA-N 3-triethoxysilylpropan-1-ol Chemical compound CCO[Si](OCC)(OCC)CCCO NMUBRRLYMADSGF-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- DTJWJHACYYLOLU-UHFFFAOYSA-N 4-(oxiran-2-yl)butane-1,2,3-triol Chemical compound OCC(O)C(O)CC1CO1 DTJWJHACYYLOLU-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
Description
本発明は、コーティング用組成物に関する。 The present invention relates to coating compositions.
ガラスやプラスチック等の基材は透明性が高く、光学フィルムやガラス、レンズ等に用いられるが、高温多湿条件下や温度差が大きい条件下では、基材表面に結露が生じて曇り、可視性が損なわれることが問題となっている。 Base materials such as glass and plastic have high transparency and are used for optical films, glasses, lenses, etc. However, under high temperature and high humidity conditions or conditions with large temperature differences, dew condensation forms on the base material surface, resulting in cloudiness and visibility. is a problem.
このような曇り現象を防止するための一般的な方法としては、基材表面に防曇効果を付与する塗膜を作製する方法が挙げられ、例えば基材表面に界面活性剤または界面活性剤と親水性ポリマーを含む溶液を塗布することにより、表面を親水化し、水滴の形成を防ぐ方法が開示されている(特許文献1)。 A common method for preventing such a clouding phenomenon is to prepare a coating film that imparts an anti-fogging effect to the substrate surface. A method of applying a solution containing a hydrophilic polymer to make the surface hydrophilic and prevent the formation of water droplets has been disclosed (Patent Document 1).
しかしながら、特許文献1の防曇性組成物は親水性が高いために被膜の耐水性が低く、水で洗い流されると効果が失われるという問題があった。また、別の方法として、塗膜表面を超撥水化することで水滴の滑落性を向上させる方法があるが(特許文献2)、塗膜表面に細かい水滴がつき、曇る現象が確認されることがある。 However, since the anti-fogging composition of Patent Document 1 is highly hydrophilic, the film has low water resistance, and there is a problem that the effect is lost when washed away with water. As another method, there is a method of making the surface of the coating film superhydrophobic to improve the slipping property of water droplets (Patent Document 2), but fine water droplets adhere to the surface of the coating film, and a clouding phenomenon is confirmed. Sometimes.
本発明は、撥水性と防曇性を併せ持つコーティング用組成物を提供することを目的とする。 An object of the present invention is to provide a coating composition having both water repellency and antifogging properties.
本発明者らが鋭意検討した結果、平均重合度が1~100の(ポリ)グリセリン骨格を有し、末端に重合性官能基を有する(ポリ)グリセリン系モノマー(A)と撥水性モノマー(B)からなるコーティング用組成物が上記課題を解決することを見出し、本発明を完成するに至った。 As a result of intensive studies by the present inventors, a (poly)glycerin-based monomer (A) having a (poly)glycerin skeleton with an average degree of polymerization of 1 to 100 and a polymerizable functional group at the end and a water-repellent monomer (B) ) to solve the above problems, and completed the present invention.
本発明の(ポリ)グリセリン系モノマーを含有するコーティング用樹脂組成物は、ガラスやプラスチック等の基材に撥水性と防曇性の両方を付与し、防曇効果の持続性に優れる。 The coating resin composition containing the (poly)glycerin-based monomer of the present invention imparts both water repellency and antifogging properties to substrates such as glass and plastics, and exhibits excellent persistence of the antifogging effect.
以下、実施形態に基づいて本発明を説明するが、本発明の範囲はこの実施形態に限定されるものではなく、本発明の趣旨を損なわない範囲で変更が加えられた形態も本発明に属する。なお、範囲を表す「~」は上限と下限を含むものである。 Hereinafter, the present invention will be described based on embodiments, but the scope of the present invention is not limited to these embodiments, and the present invention also includes forms modified within the scope of the present invention. . In addition, "-" representing a range includes an upper limit and a lower limit.
本発明に係る(ポリ)グリセリン系モノマー(A)は、平均重合度が1~100の(ポリ)グリセリン骨格を有し、末端に重合性官能基を有する。なお、(ポリ)グリセリンとは、グリセリン又はポリグリセリンを表している。 The (poly)glycerin-based monomer (A) according to the present invention has a (poly)glycerin skeleton with an average degree of polymerization of 1 to 100, and a polymerizable functional group at the end. (Poly)glycerin represents glycerin or polyglycerin.
本発明に係る(ポリ)グリセリンの平均重合度は、1~100であり、好ましくは2~20であり、最も好ましくは2~15である。ここで、平均重合度は末端分析法による水酸基価から、下記式(2)及び下記式(3)から算出される。式(3)中の水酸基価とは、(ポリ)グリセリンに含まれる水酸基数の大小の指標となる数値であり、1gの(ポリ)グリセリンに含まれる遊離水酸基をアセチル化するために必要な酢酸を中和するのに要する水酸化カリウムのミリグラム数をいう。水酸化カリウムのミリグラム数は、社団法人日本油化学会編集、「日本油化学会制定、基準油脂分析試験法、2013年度版」に準じて算出される。
分子量=74n+18 ・・・(2)
水酸基価=56110(n+2)/分子量・・・(3)
The (poly)glycerin according to the present invention has an average degree of polymerization of 1-100, preferably 2-20, most preferably 2-15. Here, the average degree of polymerization is calculated from the following formula (2) and the following formula (3) from the hydroxyl value obtained by the terminal analysis method. The hydroxyl value in formula (3) is a numerical value that is an index of the number of hydroxyl groups contained in (poly)glycerin, and the amount of acetic acid required to acetylate the free hydroxyl groups contained in 1 g of (poly)glycerin. milligrams of potassium hydroxide required to neutralize The number of milligrams of potassium hydroxide is calculated according to "Japan Oil Chemists' Society, Standard Fat Analysis Test Method, 2013 Edition" edited by the Japan Oil Chemists' Society.
Molecular weight = 74n + 18 (2)
Hydroxyl value = 56110 (n + 2) / molecular weight (3)
本発明に係る重合性官能基は特に限定されないが、アルコキシシリル基、シラノール基、アリル基やビニル基などのアルケニル基、アリルオキシ基またはビニルオキシ基などのアルケニルオキシ基、(メタ)アクリロイル基、エポキシ基、イソシアナート基などが例示できる。中でもアルコキシシリル基、アリル基、ビニル基において、本発明の効果がより発揮される。 Although the polymerizable functional group according to the present invention is not particularly limited, an alkoxysilyl group, a silanol group, an alkenyl group such as an allyl group or a vinyl group, an alkenyloxy group such as an allyloxy group or a vinyloxy group, a (meth)acryloyl group, an epoxy group , an isocyanate group, and the like. Among them, alkoxysilyl groups, allyl groups, and vinyl groups exhibit the effects of the present invention more effectively.
本発明に係る(ポリ)グリセリン系モノマー(A)は、末端に第1の反応性官能基を有する(ポリ)グリセリン又は(ポリ)グリセリン誘導体と、第2の反応性官能基を有する重合性化合物を反応させてなる反応生成物であることが好ましい。 The (poly)glycerin-based monomer (A) according to the present invention includes (poly)glycerin or a (poly)glycerin derivative having a first reactive functional group at the terminal and a polymerizable compound having a second reactive functional group. is preferably a reaction product obtained by reacting
末端に第1の反応性官能基を有する(ポリ)グリセリン又は(ポリ)グリセリン誘導体は、下記式(1)の構造で表される化合物であることが好ましい。 The (poly)glycerin or (poly)glycerin derivative having the first reactive functional group at the terminal is preferably a compound represented by the structure of formula (1) below.
AOとしては、例えば、エチレンオキサイド(EO)、プロピレンオキサイド(PO)、ブチレンオキサイド(BO)が挙げられ、好ましくはエチレンオキサイド(EO)である。式(1)記載のp、q、rはいずれもポリグリセリンの水酸基1つに対するアルキレンオキサイドの平均付加数を表しており、それぞれ0~50が好ましく、より好ましくは1~20である。また、p、q、rの和(p+q+r)は、1~130であることがより好ましく、5~120であることがさらに好ましい。 Examples of AO include ethylene oxide (EO), propylene oxide (PO) and butylene oxide (BO), preferably ethylene oxide (EO). Each of p, q, and r described in formula (1) represents the average number of additions of alkylene oxide to one hydroxyl group of polyglycerol, and each is preferably 0-50, more preferably 1-20. Further, the sum of p, q, and r (p+q+r) is more preferably 1-130, more preferably 5-120.
第1の反応性官能基を有する(ポリ)グリセリン又は(ポリ)グリセリン誘導体として具体的には、(ポリ)グリセリン、(ポリ)グリセリンアルキレンオキサイド付加物、(ポリ)グリセリン(アルキレンオキサイド)チオグリコール酸エステル、(ポリ)グリセリン(アルキレンオキサイド)3-メルカプトプロピオン酸エステル、(ポリ)グリセリン(アルキレンオキサイド)(メタ)アクリレート、(ポリ)グリセリン(アルキレンオキサイド)(ポリ)グリシジルエーテル、(ポリ)グリセリン(アルキレンオキサイド)(ポリ)アリルエーテル等が挙げられる。 Specific examples of (poly)glycerin or (poly)glycerin derivative having a first reactive functional group include (poly)glycerin, (poly)glycerin alkylene oxide adduct, (poly)glycerin (alkylene oxide) thioglycolic acid ester, (poly)glycerin (alkylene oxide) 3-mercaptopropionate, (poly)glycerin (alkylene oxide) (meth)acrylate, (poly)glycerin (alkylene oxide) (poly)glycidyl ether, (poly)glycerin (alkylene) oxide) (poly) allyl ether and the like.
第2の反応性官能基は特に限定されないが、例えばビニル基、アリル基、イソシアネート基、チオール基、(メタ)アクリロイル基、エポキシ基、水酸基、アミノ基、ヒドロシリル基等が挙げられる。第2の反応性官能基を有する重合性化合物としては、ビニルトリメトキシシラン、ビニルトリエトキシシラン、3-イソシアネートプロピルトリエトキシシラン、3-イソシアネートプロピルトリメトキシシラン、3-メルカプトプロピルメチルジメトキシシラン、3-メルカプトプロピルトリメトキシシラン、3-メタクリロキシプロピルトリメトキシシラン、3-メタクリロキシプロピルメチルジエトキシシラン、3-アクリロキシプロピルトリメトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルメチルジエトキシシラン、N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン、3-アミノプロピルトリメトキシシラン、3-ヒドロキシプロピルトリエトキシシラン、3-アミノプロピルトリエトキシシラン、トリメトキシシラン、トリエトキシシラン、ジメトキシメチルシラン、ジエトキシメチルシラン、アリルグリシジルエーテル、ジアリルグリシジルグリセリン、アリルグリシジルフタレート、アリルグリシジルヘキサヒドロフタレート、1,2-エポキシ-4-ビニルシクロヘキサン、アリルメルカプタン、ポリエチレングリコールアリルエーテル、ポリエチレングリコールジアリルエーテル、アリルジメチルアミン、ジアリルメチルアミン等が挙げられる。 Although the second reactive functional group is not particularly limited, examples thereof include vinyl group, allyl group, isocyanate group, thiol group, (meth)acryloyl group, epoxy group, hydroxyl group, amino group, hydrosilyl group and the like. Polymerizable compounds having a second reactive functional group include vinyltrimethoxysilane, vinyltriethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3 - mercaptopropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxy Propylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-aminopropyltrimethoxysilane, 3-hydroxypropyltriethoxysilane, 3-aminopropyltriethoxysilane, trimethoxysilane , triethoxysilane, dimethoxymethylsilane, diethoxymethylsilane, allyl glycidyl ether, diallyl glycidyl glycerin, allyl glycidyl phthalate, allyl glycidyl hexahydrophthalate, 1,2-epoxy-4-vinylcyclohexane, allyl mercaptan, polyethylene glycol allyl ether , polyethylene glycol diallyl ether, allyldimethylamine, diallylmethylamine, and the like.
本発明の(ポリ)グリセリン系モノマー(A)は、(ポリ)グリセリン、又は(ポリ)グリセリン誘導体の末端に含まれる第1の反応性官能基と重合性化合物に含まれる第2の反応性官能基を反応させてなるものであることが好ましい。さらには、重合性化合物の末端にある第2の反応性官能基を反応させてなるものである。具体的には、(ポリ)グリセリン、(ポリ)グリセリンアルキレンオキサイド付加物、もしくは末端にチオール基を有する(ポリ)グリセリン誘導体と、ビニル基、イソシアネート基、エポキシ基、アミノ基のいずれかを含む重合性化合物との反応生成物;末端に(メタ)アクリロイル基、もしくはアリル基を有する(ポリ)グリセリン誘導体と、ビニル基、アリル基、チオール基、(メタ)アクリロイル基、ヒドロシリル基のいずれかを有する重合性化合物との反応生成物;末端にエポキシ基を有する(ポリ)グリセリン誘導体とチオール基、水酸基、ヒドロシリル基のいずれかを含む重合性化合物との反応生成物等が挙げられる。なお、それらの得られた反応生成物において、(ポリ)グリセリン又は(ポリ)グリセリン誘導体の第1の反応性官能基のうち20~100%の第1の反応性官能基が反応して結合されていることが好ましく、50~100%の第1の反応性官能基が反応して結合されていることがさらに好ましい。 The (poly)glycerin-based monomer (A) of the present invention comprises a first reactive functional group contained at the end of (poly)glycerin or a (poly)glycerin derivative and a second reactive functional group contained in the polymerizable compound. It is preferable that the group is reacted. Furthermore, it is obtained by reacting the second reactive functional group at the end of the polymerizable compound. Specifically, polymerization containing (poly)glycerin, (poly)glycerin alkylene oxide adduct, or (poly)glycerin derivative having a thiol group at the end, and any of a vinyl group, an isocyanate group, an epoxy group, and an amino group reaction product with a volatile compound; (poly)glycerin derivative having a (meth)acryloyl group or allyl group at the end and vinyl group, allyl group, thiol group, (meth)acryloyl group, or hydrosilyl group A reaction product with a polymerizable compound; a reaction product between a (poly)glycerin derivative having an epoxy group at its end and a polymerizable compound containing any one of a thiol group, a hydroxyl group and a hydrosilyl group. In the resulting reaction product, 20 to 100% of the first reactive functional groups of the (poly)glycerin or (poly)glycerin derivative are reacted and bonded. more preferably 50-100% of the first reactive functional groups are reacted and attached.
本発明の撥水性モノマー(B)はフッ素系化合物、及びシリコーン系化合物の少なくともいずれかを含有する撥水性モノマーである。例えば、フルオロアルキル基、フルオロアルキルエーテル基、フルオロアルケニル基を有するアクリレート、シラン、シロキサン、アルコキシシラン、メトキシ基含有シリコーン樹脂、メチル系シリコーン樹脂、メチルフェニル系シリコーン樹脂等が挙げられる。 The water-repellent monomer (B) of the present invention is a water-repellent monomer containing at least one of a fluorine-based compound and a silicone-based compound. Examples include acrylates, silanes, siloxanes, alkoxysilanes, methoxy group-containing silicone resins, methyl-based silicone resins, methylphenyl-based silicone resins, and the like having fluoroalkyl groups, fluoroalkyl ether groups, and fluoroalkenyl groups.
前記(B)の分子量としては、特に制限はなく、目的に応じて適宜選択することができる。 The molecular weight of (B) is not particularly limited and can be appropriately selected depending on the purpose.
本発明のコーティング用組成物における(B)の配合量は、(A)に対して、0.01質量%以上10質量%以下であり、0.01質量% 以上5質量%以下が好ましく、0.01質量%以上1質量%以下がより好ましい。(B)の配合量が0.01質量%以上であると、撥水性を発揮する。また、(B)の配合量が10質量%以下であると、塗膜表面に白化や曇りが生じることがなく防曇性に優れる。 The amount of (B) in the coating composition of the present invention is 0.01% by mass or more and 10% by mass or less, preferably 0.01% by mass or more and 5% by mass or less, relative to (A). 01% by mass or more and 1% by mass or less is more preferable. When the blending amount of (B) is 0.01% by mass or more, water repellency is exhibited. Further, when the amount of (B) is 10% by mass or less, whitening and cloudiness do not occur on the surface of the coating film, resulting in excellent antifogging properties.
本発明のコーティング用組成物は、本発明の効果を損なわない範囲で、TMOS、TEOS等のシリケートモノマー、メチルシリケート、エチルシリケート等のシリケートオリゴマー、ポリシルセスキオキサン等を含有してもよい。 The coating composition of the present invention may contain silicate monomers such as TMOS and TEOS, silicate oligomers such as methyl silicate and ethyl silicate, polysilsesquioxane, and the like, as long as the effects of the present invention are not impaired.
また、本発明のコーティング用組成物は、その他の添加剤を添加してもよい。このような添加剤としては、紫外線吸収剤、着色剤、顔料、酸化防止剤、黄変防止剤、ブルーイング剤、消泡剤、増粘剤、沈降防止剤、帯電防止剤、界面活性剤、接着促進剤、赤外線吸収剤、光安定剤等が挙げられる。 Further, other additives may be added to the coating composition of the present invention. Such additives include ultraviolet absorbers, colorants, pigments, antioxidants, anti-yellowing agents, bluing agents, antifoaming agents, thickeners, anti-settling agents, antistatic agents, surfactants, Examples include adhesion promoters, infrared absorbers, light stabilizers, and the like.
さらに、本発明のコーティング用組成物は、有機溶媒を混合してもよい。例えば、アルコール類としては、メタノール、エタノール、ブタノール、イソブタノール、イソプロピルアルコール、プロパノール、t-ブタノール、sec-ブタノ-ル、ベンジルアルコール、ケトン類としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノン、ジアセトンアルコール、エステル系としては、酢酸エチル、酢酸メチル、酢酸ブチル、酢酸sec-ブチル、酢酸メトキシブチル、酢酸アミル、酢酸プロピル、酢酸イソプロピル、乳酸エチル、乳酸メチル、乳酸ブチル、エーテル類としては、イソプロピルエーテル、メチルセロソルブ、エチルセロソルブ、ブチルセロソルブ、グリコール類としては、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、グリコールエステル系としては、エチレングリコールモノエチルエーテルアセテート、メトキシプロピルアセテート、ブチルカルビトールアセテート、エチルカルビトールアセテート、グリコールエーテル系としては、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ブチルジグリコール、メチルトリグリコール、1-メトキシ-2-プロパノール、プロピレングリコールモノブチルエーテル、3-メトキシ-3-メチル-1-ブタノール、ジエチレングリコールモノヘキシルエーテル、プロピレングリコールモノメチルエーテルプロピオネート、ジプロピレングリコールメチルエーテル、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジエチレングリコールジエチルエーテル、芳香族炭化水素系としては、ベンゼン、トルエン、キシレンが挙げられる。これらの有機溶媒は単独、又は2種以上を併用して使用できる。 Furthermore, the coating composition of the present invention may be mixed with an organic solvent. For example, alcohols include methanol, ethanol, butanol, isobutanol, isopropyl alcohol, propanol, t-butanol, sec-butanol, benzyl alcohol, and ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, Cyclohexanone, diacetone alcohol, esters such as ethyl acetate, methyl acetate, butyl acetate, sec-butyl acetate, methoxybutyl acetate, amyl acetate, propyl acetate, isopropyl acetate, ethyl lactate, methyl lactate, butyl lactate, ethers is isopropyl ether, methyl cellosolve, ethyl cellosolve, butyl cellosolve, glycols are ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, glycol esters are ethylene glycol monoethyl ether acetate, methoxypropyl acetate, butyl carbitol Acetate, ethyl carbitol acetate, glycol ethers include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, butyl diglycol, methyltriglycol, 1-methoxy-2-propanol, propylene glycol monobutyl ether, 3-methoxy-3-methyl -1-butanol, diethylene glycol monohexyl ether, propylene glycol monomethyl ether propionate, dipropylene glycol methyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol diethyl ether, aromatic hydrocarbons such as benzene, Toluene and xylene are mentioned. These organic solvents can be used alone or in combination of two or more.
本発明のコーティング用組成物を各種基材に塗布して硬化させることにより、硬化塗膜を作製することができる。硬化方法は特に限定されないが、光硬化、熱硬化、ゾル-ゲル反応による硬化など、コーティング用組成物の反応基によって公知の方法を使用できる。 A cured coating film can be produced by applying the coating composition of the present invention to various substrates and curing the composition. The curing method is not particularly limited, but known methods such as photocuring, heat curing, and curing by sol-gel reaction can be used depending on the reactive group of the coating composition.
本発明のコーティング用組成物を光や熱により硬化させる場合、重合開始剤を用いることが好ましい。 When the coating composition of the present invention is cured by light or heat, it is preferable to use a polymerization initiator.
光重合開始剤としては特に限定されないが、2,2-ジメトキシ-1,2-ジフェニルエタン-1-オン等のベンジルケタール類、1-ヒドロキシシクロヘキシルフェニルケトン、1-[4-(2-ヒドロキシエトキシ)フェニル]-2-ヒドロキシ-2-メチル-1-プロパン-1-オン、2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン等のα-ヒドロキシアセトフェノン類、2-ベンジル-2-ジメチルアミノ-1-(4-モルフォリノフェニル)ブタノン-1、2-メチル-1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパン-1-オン等のアミノアセトフェノン類、ビス(2,4,6-トリメチルベンゾイル)フェニルフォスフィンオキサイド、ビス(2,6-ジメトキシベンゾイル)-2,4,4-トリメチルペンチルフォスフィンオキサイド、モノアシルフォスフィンオキサイド等のアシルフォスフィンオキサイド類、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインブチルエーテル、ベンゾインイソプロピルエーテル等のベンゾイン類、ベンゾフェノン、メチルベンゾフェノン、4,4’-ビスジエチルアミノベンゾフェノン、4-ベンゾイル-4’-メチルジフェニルサルファイド等のベンゾフェノン類、2,4-ジエチルチオキサントン、2-クロロチオキサントン、2-イソプロピルチオキサントン等のチオキサントン類等の光ラジカル重合開始剤、ジアゾニウム塩、ヨードニウム塩、スルホニウム塩、ホスホニウム塩などのオニウム塩系の化合物、鉄アレーン錯体に代表される有機金属錯体や、トロピリウムに代表されるカルボカチオン塩等の光カチオン重合開始剤(光酸発生剤)、オキシムエステル系化合物、アンモニウム系化合物、ベンゾイン系化合物、ジメトキシベンジルウレタン系化合物、オルトニトロベンジルウレタン系化合物等の光アニオン重合開始剤(光塩基発生剤)が挙げられる。光重合開始剤の使用量は特に限定されないが、一般に、コーティング用組成物を構成する(ポリ)グリセリン系モノマー及び撥水性モノマーの合計量100重量部に対して、0.1~10重量部が好ましい。 Although the photopolymerization initiator is not particularly limited, benzyl ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxycyclohexylphenyl ketone, 1-[4-(2-hydroxyethoxy ) Phenyl]-2-hydroxy-2-methyl-1-propan-1-one, α-hydroxyacetophenones such as 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-benzyl-2- Aminoacetophenones such as dimethylamino-1-(4-morpholinophenyl)butanone-1, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, bis(2, 4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, acylphosphine oxides such as monoacylphosphine oxide, benzoin, benzoin benzoins such as methyl ether, benzoin ethyl ether, benzoin butyl ether, benzoin isopropyl ether; benzophenones such as benzophenone, methylbenzophenone, 4,4'-bisdiethylaminobenzophenone, 4-benzoyl-4'-methyldiphenylsulfide; typified by photoradical polymerization initiators such as thioxanthones such as diethylthioxanthone, 2-chlorothioxanthone and 2-isopropylthioxanthone, onium salt compounds such as diazonium salts, iodonium salts, sulfonium salts and phosphonium salts, and iron arene complexes. photocationic polymerization initiators (photoacid generators) such as organometallic complexes, carbocation salts such as tropylium, oxime ester compounds, ammonium compounds, benzoin compounds, dimethoxybenzyl urethane compounds, orthonitrobenzyl Photoanionic polymerization initiators (photobase generators) such as urethane-based compounds are included. The amount of the photopolymerization initiator used is not particularly limited, but in general, 0.1 to 10 parts by weight is used with respect to 100 parts by weight of the total amount of the (poly)glycerin-based monomer and the water-repellent monomer constituting the coating composition. preferable.
熱重合開始剤としては、2,2‘-アゾビスブチロニトリル(AIBN)に代表されるアゾ化合物、過酸化ベンゾイル(BPO)に代表される過酸化物等の熱ラジカル重合開始剤、ベンゼンスルホン酸エステルやアルキルスルホニウム塩等の熱カチオン重合開始剤が挙げられる。熱重合開始剤の使用量は特に限定されないが、一般に、コーティング用組成物を構成する(ポリ)グリセリン系モノマー及び撥水性モノマーの合計量100重量部に対して、0.1~20重量部が好ましい。 Thermal polymerization initiators include azo compounds typified by 2,2'-azobisbutyronitrile (AIBN), thermal radical polymerization initiators such as peroxides typified by benzoyl peroxide (BPO), benzenesulfone Examples thereof include thermal cationic polymerization initiators such as acid esters and alkylsulfonium salts. The amount of the thermal polymerization initiator to be used is not particularly limited, but is generally 0.1 to 20 parts by weight with respect to 100 parts by weight of the total amount of the (poly)glycerin-based monomer and the water-repellent monomer constituting the coating composition. preferable.
本発明のコーティング用組成物をゾル-ゲル反応で硬化させる場合、金属アルコキシドの加水分解に必要な水を加える。また、金属アルコキシドの加水分解と重縮合反応を促進させるために触媒を用いることが好ましく、その触媒としては、従来のゾル-ゲル法で使用される酸触媒及びアルカリ触媒でよい。酸触媒としては塩酸、硝酸、硫酸、ギ酸、有機酸、光酸発生剤等が挙げられる。また、アルカリ触媒としては金属水酸化物やアンモニア等の無機塩基化合物、アミン類、ホスフィン類等の有機塩基化合物、光塩基発生剤等が挙げられる。 When the coating composition of the present invention is cured by a sol-gel reaction, water necessary for hydrolysis of the metal alkoxide is added. In addition, it is preferable to use a catalyst to promote the hydrolysis and polycondensation reaction of the metal alkoxide, and the catalyst may be an acid catalyst or an alkali catalyst used in the conventional sol-gel method. Acid catalysts include hydrochloric acid, nitric acid, sulfuric acid, formic acid, organic acids, photoacid generators and the like. Examples of alkali catalysts include inorganic base compounds such as metal hydroxides and ammonia, organic base compounds such as amines and phosphines, and photobase generators.
本発明のコーティング用組成物は、撥水防曇性付与剤や結露防止剤、応力緩和剤として好適に用いることができる。このようなコーティング用組成物を硬化させて得られる硬化塗膜は、ガラスやプラスチック等の基材に対して防曇性に優れるものであり、自動車のフロントガラス、ランプカバー、カメラレンズ、ゴーグル等の防曇コーティング剤として好適に用いられる。 The coating composition of the present invention can be suitably used as a water-repellent and anti-fogging agent, an anti-condensing agent, and a stress relaxation agent. A cured coating film obtained by curing such a coating composition has excellent anti-fogging properties for substrates such as glass and plastics, and is used for automobile windshields, lamp covers, camera lenses, goggles, etc. is suitably used as an anti-fogging coating agent.
以下に実施例を挙げて本発明を説明するが、本発明はこれらによって何らの限定を受けるものではない。 The present invention will be described below with reference to examples, but the present invention is not limited by these examples.
[合成例1]
温度計、撹拌機を備えた反応容器に、テトラグリセリンのEO60モル付加物425g、3-イソシアネートプロピルトリエトキシシラン(TCI製)210g、ジラウリン酸ジブチルすず0.13gを仕込み、40℃で4時間撹拌し、化合物(A1)を635g得た。なお、ポリグリセリン誘導体の末端にある水酸基の100%を反応させた。
[Synthesis Example 1]
A reaction vessel equipped with a thermometer and a stirrer was charged with 425 g of EO60 mol adduct of tetraglycerin, 210 g of 3-isocyanatopropyltriethoxysilane (manufactured by TCI), and 0.13 g of dibutyltin dilaurate, and stirred at 40° C. for 4 hours. and 635 g of compound (A1) was obtained. Note that 100% of the hydroxyl groups at the ends of the polyglycerol derivative were reacted.
[合成例2]
温度計、撹拌機を備えた反応容器に、テトラグリセリンのEO60モル付加物80g、3-イソシアネートプロピルトリエトキシシラン(TCI製)20g、ジラウリン酸ジブチルすず0.01gを仕込み、60℃で6時間撹拌し、化合物(A2)を100g得た。なお、ポリグリセリン誘導体の末端にある水酸基のうち50%を反応させた。
[Synthesis Example 2]
A reaction vessel equipped with a thermometer and a stirrer was charged with 80 g of EO60 mol adduct of tetraglycerin, 20 g of 3-isocyanatopropyltriethoxysilane (manufactured by TCI), and 0.01 g of dibutyltin dilaurate, and stirred at 60° C. for 6 hours. and 100 g of compound (A2) was obtained. Note that 50% of the hydroxyl groups at the ends of the polyglycerol derivative were reacted.
[合成例3]
温度計、撹拌機を備えた反応容器に、テトラグリセリンのEO12モル付加物37g、3-イソシアネートプロピルトリエトキシシラン(TCI製)63g、ジラウリン酸ジブチルすず0.01gを仕込み、60℃で5時間撹拌し、化合物(A3)を100g得た。なお、ポリグリセリン誘導体の末端にある水酸基の100%を反応させた。
[Synthesis Example 3]
A reaction vessel equipped with a thermometer and a stirrer was charged with 37 g of EO 12 mol adduct of tetraglycerin, 63 g of 3-isocyanatopropyltriethoxysilane (manufactured by TCI), and 0.01 g of dibutyltin dilaurate, and stirred at 60° C. for 5 hours. and 100 g of compound (A3) was obtained. Note that 100% of the hydroxyl groups at the ends of the polyglycerol derivative were reacted.
[合成例4]
温度計、撹拌機を備えた反応容器に、ジグリセリンのEO40モル付加物66g、3-イソシアネートプロピルトリエトキシシラン(TCI製)34g、ジラウリン酸ジブチルすず0.01gを仕込み、60℃で12時間撹拌し、化合物(A4)を100g得た。なお、ポリグリセリン誘導体の末端にある水酸基の100%を反応させた。
[Synthesis Example 4]
A reaction vessel equipped with a thermometer and a stirrer was charged with 66 g of EO40 mol adduct of diglycerin, 34 g of 3-isocyanatopropyltriethoxysilane (manufactured by TCI), and 0.01 g of dibutyltin dilaurate, and stirred at 60° C. for 12 hours. and 100 g of compound (A4) was obtained. Note that 100% of the hydroxyl groups at the ends of the polyglycerol derivative were reacted.
[合成例5]
温度計、撹拌機を備えた反応容器に、デカグリセリンのEO120モル付加物66g、3-イソシアネートプロピルトリエトキシシラン(TCI製)34g、ジラウリン酸ジブチルすず0.01gを仕込み、40℃で4時間撹拌し、化合物(A5)を100g得た。なお、ポリグリセリン誘導体の末端にある水酸基の100%を反応させた。
[Synthesis Example 5]
A reaction vessel equipped with a thermometer and a stirrer was charged with 66 g of EO 120 mol adduct of decaglycerin, 34 g of 3-isocyanatopropyltriethoxysilane (manufactured by TCI), and 0.01 g of dibutyltin dilaurate, and stirred at 40°C for 4 hours. and 100 g of compound (A5) was obtained. Note that 100% of the hydroxyl groups at the ends of the polyglycerol derivative were reacted.
[合成例6]
温度計、撹拌機、ディーンスターク装置を備えた反応容器に、テトラグリセリン(平均重合度4のポリグリセリン)のEO60モル付加物764g、3-メルカプトプロピオン酸163g、トルエン900g、p-トルエンスルホン酸45gを仕込み、撹拌しながらトルエン還流雰囲気まで昇温し、約6時間かけて脱水縮合反応を行った。反応終了後、炭酸水素ナトリウムを用いて中和し、酢酸エチル:トルエン=50:50で抽出した。有機層を減圧留去することにより、テトラグリセリンEO60モル付加物の3-メルカプトプロピオン酸エステル367gを得た。撹拌機を備えた反応容器に、テトラグリセリンEO60モル付加物の3-メルカプトプロピオン酸エステル319gとビニルトリメトキシシラン81gを仕込み、UV光を照射しながら45分撹拌し、化合物(A6)を400g得た。なお、ポリグリセリン誘導体の末端にある水酸基の100%を反応させた。
[Synthesis Example 6]
Into a reaction vessel equipped with a thermometer, a stirrer and a Dean-Stark apparatus, 764 g of EO60 molar adduct of tetraglycerin (polyglycerin with an average degree of polymerization of 4), 163 g of 3-mercaptopropionic acid, 900 g of toluene and 45 g of p-toluenesulfonic acid. was charged, the temperature was raised to a toluene reflux atmosphere while stirring, and dehydration condensation reaction was carried out over about 6 hours. After completion of the reaction, the reaction mixture was neutralized with sodium hydrogencarbonate and extracted with ethyl acetate:toluene=50:50. By distilling off the organic layer under reduced pressure, 367 g of 3-mercaptopropionate of tetraglycerol EO 60 mol adduct was obtained. In a reactor equipped with a stirrer, 319 g of 3-mercaptopropionate of tetraglycerin EO 60 mol adduct and 81 g of vinyltrimethoxysilane were charged and stirred for 45 minutes while irradiating with UV light to obtain 400 g of compound (A6). rice field. Note that 100% of the hydroxyl groups at the ends of the polyglycerol derivative were reacted.
[合成例7]
温度計、撹拌機を備えた反応容器に、テトラグリセリンのEO12モル付加物10g、50%水酸化トリウム水溶液16.7g、テトラブチルアンモニウムブロミド2.24gを仕込み、40℃にて撹拌した。そこへ臭化アリル25.3gを滴下し、40℃で加熱しながら22時間撹拌した。反応終了後、トルエンにて抽出し、溶媒を減圧留去することでテトラグリセリンのEO12モル付加物のアリルエーテルを合成した。続いて、テトラグリセリンのEO12モル付加物のアリルエーテル10.0g、トリエトキシシラン6.22gを仕込み、Karstedt´s触媒存在下、室温にて撹拌することで、化合物(A7)を16g得た。
[Synthesis Example 7]
A reaction vessel equipped with a thermometer and a stirrer was charged with 10 g of EO 12 mol adduct of tetraglycerin, 16.7 g of 50% thorium hydroxide aqueous solution, and 2.24 g of tetrabutylammonium bromide and stirred at 40°C. 25.3 g of allyl bromide was added dropwise thereto, and the mixture was stirred for 22 hours while being heated at 40°C. After completion of the reaction, extraction was performed with toluene, and the solvent was distilled off under reduced pressure to synthesize an allyl ether of 12 mol of EO adduct of tetraglycerin. Subsequently, 10.0 g of allyl ether of EO 12 mol adduct of tetraglycerol and 6.22 g of triethoxysilane were charged and stirred at room temperature in the presence of Karstedt's catalyst to obtain 16 g of compound (A7).
[合成例8]
スクリュー管に含ケイ素フッ素樹脂9.10g、酢酸エチル32.2g、3-イソシアネートプロピルトリエトキシシラン(TCI製)0.28g、ジラウリン酸ジブチルすず100ppm(対理論収量)を仕込み、40℃で24時間撹拌することで、濃度が5wt%の化合物(B1)を42g得た。
[Synthesis Example 8]
A screw tube was charged with 9.10 g of silicon-containing fluororesin, 32.2 g of ethyl acetate, 0.28 g of 3-isocyanatopropyltriethoxysilane (manufactured by TCI), and 100 ppm of dibutyltin dilaurate (relative to theoretical yield), and the mixture was heated at 40° C. for 24 hours. By stirring, 42 g of compound (B1) having a concentration of 5 wt % was obtained.
<実施例1>
化合物(A1)1.0g、化合物(B1)濃度5wt%酢酸エチル溶液0.20g、1-メトキシ-2-プロパノール1.0g、水0.37g、ギ酸0.3gを均一に撹拌混合して、コーティング用組成物を得た。そして、親水化処理を施したガラス板(76mm×52mm×1.2mm)に上記コーティング用組成物を塗布し、室温で1時間風乾後、150℃で30分間加温乾燥することで、膜厚が約27μmの硬化塗膜を得た。なお、ガラス板は、アルカリ溶液(イソプロパノール500mL、水酸化カリウム41.6g、イオン交換水83.3gを混合した溶液)に15時間浸漬し、0.2mol/Lの塩酸水溶液とイオン交換水で洗浄することで親水化処理した。
<Example 1>
1.0 g of compound (A1), 0.20 g of a 5 wt % ethyl acetate solution of compound (B1), 1.0 g of 1-methoxy-2-propanol, 0.37 g of water, and 0.3 g of formic acid are uniformly stirred and mixed, A coating composition was obtained. Then, the above coating composition is applied to a glass plate (76 mm × 52 mm × 1.2 mm) that has been subjected to a hydrophilic treatment, air-dried at room temperature for 1 hour, and then heated and dried at 150 ° C. for 30 minutes to obtain a film thickness. A cured coating film having a thickness of about 27 µm was obtained. The glass plate was immersed in an alkaline solution (mixed solution of 500 mL of isopropanol, 41.6 g of potassium hydroxide, and 83.3 g of ion-exchanged water) for 15 hours and washed with a 0.2 mol/L hydrochloric acid aqueous solution and ion-exchanged water. Hydrophilic treatment was performed by
得られた硬化塗膜について、以下のとおり撥水性、防曇性を評価した。
(撥水性)
撥水性は硬化塗膜面の水接触角により評価した。接触角測定装置(Drop Master DM500、協和界面科学株式会社製)を用い、硬化塗膜にイオン交換水を1μL滴下し、着液から60秒経過後の接触角を測定した。
(防曇性)
硬化塗膜を50℃に調温した水の液面から2.0cm上部に設置し、硬化塗膜が曇るか否かを目視で評価し、塗膜が曇り始めた時間を測定した。
The resulting cured coating film was evaluated for water repellency and antifogging properties as follows.
(water repellency)
The water repellency was evaluated by the water contact angle on the surface of the cured coating film. Using a contact angle measurement device (Drop Master DM500, manufactured by Kyowa Interface Science Co., Ltd.), 1 μL of ion-exchanged water was dropped on the cured coating film, and the contact angle was measured 60 seconds after the contact with the liquid.
(Anti-fogging property)
The cured coating film was placed 2.0 cm above the liquid surface of water adjusted to a temperature of 50° C., and whether or not the cured coating film became cloudy was visually evaluated, and the time at which the coating film started to become cloudy was measured.
<実施例2~7>
実施例1で使用した化合物(A1)を化合物(A2)~(A7)に変更し、それに伴い水の量を変化させたこと以外は実施例1と同様にコーティング用組成物および硬化塗膜を作製し、撥水性、防曇性を評価した。
<Examples 2 to 7>
A coating composition and a cured coating film were prepared in the same manner as in Example 1 except that the compound (A1) used in Example 1 was changed to compounds (A2) to (A7) and the amount of water was changed accordingly. It was prepared and evaluated for water repellency and antifogging properties.
<実施例8>
実施例1で使用した化合物(B1)の添加量を1部から0.3部に変更し、それに伴い水の量を変化させたこと以外は実施例1と同様にコーティング用組成物および硬化塗膜を作製し、撥水性、防曇性を評価した。
<Example 8>
A coating composition and a cured coating were prepared in the same manner as in Example 1 except that the amount of compound (B1) used in Example 1 was changed from 1 part to 0.3 parts, and the amount of water was changed accordingly. A film was prepared and evaluated for water repellency and antifogging properties.
<実施例9>
実施例1で使用した化合物(B1)の添加量を1部から2部に変更し、それに伴い水の量を変化させたこと以外は実施例1と同様にコーティング用組成物および硬化塗膜を作製し、撥水性、防曇性を評価した。
<Example 9>
A coating composition and a cured coating film were prepared in the same manner as in Example 1, except that the amount of compound (B1) used in Example 1 was changed from 1 part to 2 parts, and the amount of water was accordingly changed. It was prepared and evaluated for water repellency and antifogging properties.
<参考例1>
化合物(A1)1.0g、1-メトキシ-2-プロパノール1.0g、水0.37g、ギ酸0.3gを均一に撹拌混合して、コーティング用組成物を得た。そして、親水化処理を施したガラス板(76mm×52mm×1.2mm)に上記コーティング用組成物を塗布し、室温で1時間風乾後、150℃で30分間加温乾燥することで、膜厚が約30μmの硬化塗膜を得た。得られた硬化塗膜について、実施例1~9と同様に、撥水性、防曇性を評価した。
<Reference example 1>
1.0 g of compound (A1), 1.0 g of 1-methoxy-2-propanol, 0.37 g of water and 0.3 g of formic acid were uniformly stirred and mixed to obtain a coating composition. Then, the above coating composition is applied to a glass plate (76 mm × 52 mm × 1.2 mm) that has been subjected to a hydrophilic treatment, air-dried at room temperature for 1 hour, and then heated and dried at 150 ° C. for 30 minutes to obtain a film thickness. A cured coating film having a thickness of about 30 µm was obtained. The resulting cured coating film was evaluated for water repellency and antifogging properties in the same manner as in Examples 1-9.
実施例1~9、参考例1の配合組成、及び評価結果を表1、表2に示した。 Tables 1 and 2 show the formulations and evaluation results of Examples 1 to 9 and Reference Example 1.
本発明の(ポリ)グリセリン系モノマー(A)と撥水性モノマー(B)から成るコーティング用組成物の硬化塗膜である実施例1は、(ポリ)グリセリン系モノマー(A)のみから成る参考例1に比べて、高い撥水性と防曇性を有するものであった。また、(ポリ)グリセリン系モノマー(A)の構造が変更された実施例2~7も同様の性能が得られることを確認した。さらに、撥水性モノマー(B)の添加量を変更した場合も、同様の効果が得られた。以上の評価結果より、本発明のコーティング用組成物から得られる硬化塗膜は、吸放湿性を有し撥水性と防曇性を両立させることが明らかとなった。 Example 1, which is a cured coating film of a coating composition comprising the (poly)glycerin-based monomer (A) and the water-repellent monomer (B) of the present invention, is a reference example comprising only the (poly)glycerin-based monomer (A). Compared to No. 1, it had higher water repellency and anti-fogging properties. Further, it was confirmed that Examples 2 to 7, in which the structure of the (poly)glycerin-based monomer (A) was changed, also provided similar performance. Furthermore, similar effects were obtained when the amount of the water-repellent monomer (B) added was changed. From the above evaluation results, it was clarified that the cured coating film obtained from the coating composition of the present invention has moisture absorption and release properties, and has both water repellency and antifogging properties.
Claims (8)
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