JP7382309B2 - 接着促進剤およびその使用 - Google Patents
接着促進剤およびその使用 Download PDFInfo
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- JP7382309B2 JP7382309B2 JP2020511390A JP2020511390A JP7382309B2 JP 7382309 B2 JP7382309 B2 JP 7382309B2 JP 2020511390 A JP2020511390 A JP 2020511390A JP 2020511390 A JP2020511390 A JP 2020511390A JP 7382309 B2 JP7382309 B2 JP 7382309B2
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- 239000002318 adhesion promoter Substances 0.000 title description 64
- 239000000758 substrate Substances 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 229920000642 polymer Polymers 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 53
- 150000001282 organosilanes Chemical class 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 239000008199 coating composition Substances 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- -1 3-glycidyloxypropyl Chemical group 0.000 description 40
- 239000011521 glass Substances 0.000 description 30
- 238000000576 coating method Methods 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 230000003197 catalytic effect Effects 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000000524 functional group Chemical group 0.000 description 16
- 125000004474 heteroalkylene group Chemical group 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 13
- 239000012528 membrane Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- CNYYCMIHRZNCPH-UHFFFAOYSA-N [Na+].[Na+].[Na+].[O-][SiH3].[O-][SiH3].[O-][SiH3] Chemical compound [Na+].[Na+].[Na+].[O-][SiH3].[O-][SiH3].[O-][SiH3] CNYYCMIHRZNCPH-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 239000012790 adhesive layer Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000006664 bond formation reaction Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- QVNXSWYMVGTSSE-UHFFFAOYSA-N 1,2-bis(trichlorosilyl)ethyl-trichlorosilane Chemical compound Cl[Si](Cl)(Cl)CC([Si](Cl)(Cl)Cl)[Si](Cl)(Cl)Cl QVNXSWYMVGTSSE-UHFFFAOYSA-N 0.000 description 4
- KDZDISUAXMZDLZ-UHFFFAOYSA-N 1,2-bis(triethoxysilyl)ethyl-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CC([Si](OCC)(OCC)OCC)[Si](OCC)(OCC)OCC KDZDISUAXMZDLZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 229910018557 Si O Inorganic materials 0.000 description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 150000001343 alkyl silanes Chemical class 0.000 description 4
- 239000000919 ceramic Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000005357 flat glass Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XNGXXLLKIOMYNW-UHFFFAOYSA-N triethoxy(2-penta-1,4-dien-3-ylsilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[SiH2]C(C=C)C=C XNGXXLLKIOMYNW-UHFFFAOYSA-N 0.000 description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229910008051 Si-OH Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910002808 Si–O–Si Inorganic materials 0.000 description 2
- 229910006358 Si—OH Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000002241 glass-ceramic Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 150000004819 silanols Chemical class 0.000 description 2
- 229910052990 silicon hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 2
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910018626 Al(OH) Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000252506 Characiformes Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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Images
Classifications
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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Description
式(I)の式中、各Rは同じまたは異なっており、水素または非水素の置換基であってよく、L1はリンカー基であり、yは正の整数である。
式(II)の式中、各Rは同じまたは異なっており、水素または非水素の置換基であってよく、各L1は同じまたは異なるリンカー基であり、yおよびzは同じまたは異なっており、それぞれが正の整数である。
前述の式(II)、(IV)および(V)の式中、R1、R2、R3、m、n、p、q、r、r1およびr2は本明細書に記載の通りである
式(I)中、各Rは同じまたは異なっており、水素または非水素の置換基であってよく、L1はリンカー基であり、yは正の整数である。
式(IA)中、各Rは同じまたは異なっており、水素または非水素の置換基であってよく、L2はリンカー基であり、yは正の整数であり、
式(II)中、各Rは同じまたは異なっており、水素または非水素の置換基であってよく、各L1は同じまたは異なるリンカー基であり、yおよびzは同じまたは異なっており、それぞれが正の整数である。
式(IIA)中、各Rは同じまたは異なっており、水素または非水素の置換基であってよく、各XおよびX’は同じまたは異なっており、水素または非水素の置換基であってよく、各xは同じまたは異なる正の整数であり、yおよびzはそれぞれ同じまたは異なる正の整数であり、
式(III)、(IV)および(V)中、
R1は長鎖アルキルまたは長鎖フッ素化されたアルキルであり、
R2およびR3は、C1-C15アルキル、C2-C15アルケニル、-NCO、-CH(O)CH2、-NH2、-NHC1-C6アルキル、-OC(O)NHC1-C6アルキル、OC(O)NH2、-P(O)(OC1-C6アルキル)2、-C1-C6アルキルSi(C1-C6アルキル)3、-C1-C6アルキルSi(C1-C6アルキル)2(OC1-C6アルキル)、-C1-C6アルキルSi(C1-C6アルキル)(OC1-C6アルキル)2、-C1-C6アルキルSi(OC1-C6アルキル)3、-Si(C1-C6アルキル)2(OC1-C6アルキル)、-Si(C1-C6アルキル)(OC1-C6アルキル)2および-Si(OC1-C6アルキル)3から成る群からそれぞれ独立して選択され、C1-C15アルキルまたはC1-C6アルキル中の1つ以上の水素原子が、任意には-OC(O)C1-C4アルケニル、-NCO、-(OC1-C4アルキル)-CH(O)CH2、-CH(O)CH2、-NH2、-NHC1-C4アルキル、-OC(O)NHC1-C4アルキル、-OC(O)NH2、-P(O)(OC1-C4アルキル)2、-Si(C1-C4アルキル)2(OC1-C4アルキル)、-Si(C1-C4アルキル)(OC1-C4アルキル)2または-Si(OC1-C4アルキル)3で独立して任意には置換され、
mは0~7の整数であり、
nは0~7の整数であり、
pは0~6の整数であり、
qは0~6の整数であり、
nおよびmの合計が、7以下であり、pおよびqの合計が6以下である。
本明細書に記載されるプロセスおよび物品に関し、適用されるトップコートに関する特別な制限はない。トップコートの個性は、製造されている物品が使用される用途または産業、トップコートが適用されている基材の型、コーティングされた表面などに所望される化学的および/または物理的特性といったような要因によって変化し得る。例えば、いくつかの実施形態では、例えばフロントガラスといった自動車分野で使用されるガラス基材といったものの上に、オムニフォビックコーティングを有するコーティングされた基材を調製することが望ましい場合がある。このような代表的な一実施形態では、オムニフォビックコーティングは、参照として本明細書に組み込まれる国際公開第2016/201028号に記載される、C8F17(CH2)2Si(OEt)3またはF--FPOSSといったフッ素化シランであり得る。本開示では、本明細書に記載される追加の接着促進剤を有するかまたは有さないシラン官能基を含む、本明細書に記載される接着促進剤接着促進剤を使用することにより、向上した耐久性といった、向上した特性を有する、コーティングされた基材を提供し得る。
本発明が適用される基材に関する特別な制限はない。例えば、基材には、金属、プラスチック、ガラス、セラミックまたは他の無機材料、有機材料または複合材材料、積層材料などといったこれらの組合せが挙げられる。更に、基材表面は基材表面それ自身であってよいか、またはコーティングされる金属プレートのコーティング表面もしくは表面処理ガラスの表面処理層の表面といった、基材表面とは異なる材料表面であってよい。基材形状に関しては、必ずしも平板でなくてもよく、また特定の目的によっては、表面全体にわたって、またはその一部に湾曲部を有するものといった任意の形状を有してよい。これはフルエッジトゥエッジスクリーン向けに丸い端部を有する携帯電話スクリーンといったものである。
以下の実施例は例示のみを目的として記述される。こうした実施例にて明らかになっている部分および割合は、特に指示のない限り重量基準である。
触媒量のKOH水溶液を加えた、4.48gの3-イソシアネートプロピルトリエトキシシラン(18.11mmol、14eq)および0.45gの1,2-ビス(トリエトキシシリル)エタン(1.26mmol、1eq)を室温のエタノールに溶解させ、5時間攪拌した。反応混合物に酢酸エチルを加え、2、3回蒸留水で洗浄した。有機ろ過液をMgSO4で乾燥させ、真空下で溶媒を蒸発させて、2.32gの淡黄色油(1.26mmol、収率定量的)を得た。
プラズマ活性化を行うため、プライマー層を与えられる基材は、低圧PECVD(プラズマ励起化学気相成膜)反応器のチャンバ内に設置された。少なくとも5mPa(5・10-5mbar)のチャンバ内の残圧は、導入されるガスの活性化よりも前に最初に生じた。ガラス基材を表面処理するため、反応器内の全圧が350mTorrとなるまで100sccmの流量にて、ガスまたはガス混合物がチャンバ内へと導入された。
20mlのエタノールおよび0.08gのトリスPAP(トリスホスファゼニルホスフィン)からエタノール溶液を調製し、30分間十分に攪拌した。0.15mlの硝酸をエタノール溶液に添加した。プラズマ表面処理済ガラス(4”×4”)を溶液に2分間浸漬させ、室温にて乾燥させた。20mlのエタノールおよびgのF-POSSおよび150uLの硝酸を加えたgのフルオロアルキルシランからトップコーティング溶液を調製した。乾燥させたガラス表面を、疎水性コーティング溶液に30分間浸漬させた。コーティングされたガラス表面を、75℃のオーブンで少なくとも2時間乾燥させた。
2つの異なる疎水性サンプル(トリスPAPを加えたものおよびトリスPAPが加えられていないもの)の濡れ性を、水およびヘキサデカンといった異なる液体を用いた接触角測定によって評価した。トリスPAPなしの疎水性コーティングおよびトリスPAPによる疎水性コーティングに関する、上記手順により調製された試験片より得られた結果を、以下の表1および表2に示す。
得られたオムニフォビック基材の耐摩耗性は、ASTM D4060によって測定された。試験は、50サイクル/分の並進速度および6rpmの回転速度で、1.5cm2の領域上に250gの荷重をかけ、CS-10硬度の摩耗輪を用いて試験片上で実施した。仮に、1500サイクル後、接触角が70度より大きいままの状態である場合には、当該試験においては、試験片は良好であると考えられた。機械的摩耗(ASTM D4060テーバー)試験(500gの荷重で1,500サイクル(CS-10ホイール))の結果を示すチャートである図6に示されるように、試験片の耐摩耗特性は十分なものであり、水接触角はほんのわずかでも低下することがなかったことが確認され得る。
Claims (17)
- 前記1つ以上のポリマーが、1000以上の重量平均分子量を有する、請求項1に記載の基材。
- 前記1つ以上のポリマーが、4000以上の重量平均分子量を有する、請求項1に記載の基材。
- 各Rがエチルである、請求項1~8のいずれか1項に記載の基材。
- 溶媒成分を更に含む、請求項13に記載のコーティング組成物。
- 前記溶媒成分がC1-6アルコールを含む、請求項16に記載のコーティング組成物。
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