JP2017061439A - Surface active silane coupling agent - Google Patents
Surface active silane coupling agent Download PDFInfo
- Publication number
- JP2017061439A JP2017061439A JP2015200702A JP2015200702A JP2017061439A JP 2017061439 A JP2017061439 A JP 2017061439A JP 2015200702 A JP2015200702 A JP 2015200702A JP 2015200702 A JP2015200702 A JP 2015200702A JP 2017061439 A JP2017061439 A JP 2017061439A
- Authority
- JP
- Japan
- Prior art keywords
- coupling agent
- silane coupling
- group
- formula
- functional group
- 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
Links
- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 45
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000524 functional group Chemical group 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 15
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 235000019441 ethanol Nutrition 0.000 description 30
- 239000000243 solution Substances 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- -1 polyethylene terephthalate Polymers 0.000 description 10
- 239000011521 glass Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003377 silicon compounds Chemical class 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Abstract
Description
本発明は、防曇効果が大きく、低コストで製造できるコーティング可能な防曇剤の成分として重要な界面活性シランカップリング剤に関する。 The present invention relates to a surface active silane coupling agent that is important as a component of a coatable antifogging agent that has a large antifogging effect and can be produced at low cost.
表面親水化剤として、本発明者らは既にスルホン酸基を持つ修飾金属酸化物ゾルを特許として取得している（特許文献１）。しかし、従来の修飾金属酸化物ゾルからなる親水性コーティング液で処理した基材（ガラス、プラスチック及び金属等）は親水性を示すが、防曇性がなく、レンズ等に処理した場合、水蒸気に暴露すると水滴が発生し、視界が不良となる問題がある。
また、防曇剤の特許としては、リン酸エステル型乳化剤を使用する防曇剤（特許文献２）、ポリアクリル酸類を使用する防曇剤（特許文献３）等が、出願されている。
As the surface hydrophilizing agent, the present inventors have already obtained a patent for a modified metal oxide sol having a sulfonic acid group (Patent Document 1). However, base materials (glass, plastics, metals, etc.) treated with a hydrophilic coating solution made of a conventional modified metal oxide sol show hydrophilicity, but are not anti-fogging. When exposed, water droplets are generated, resulting in poor visibility.
Further, as an antifogging agent patent, an antifogging agent using a phosphoric acid ester type emulsifier (Patent Document 2), an antifogging agent using a polyacrylic acid (Patent Document 3), and the like have been filed.
本発明の目的は、水蒸気に暴露しても全く曇らない、防曇剤の成分として好適な界面活性シランカップリング剤を提供することである。 An object of the present invention is to provide a surface-active silane coupling agent suitable as a component of an antifogging agent that does not become cloudy even when exposed to water vapor.
本発明の界面活性シランカップリング剤は、
下記式（１）で表される化合物と
Ｒ１−Ｘ−（ＣＨ２ＣＨ２Ｏ）ｎ−Ｙ （１）
｛式中Ｒ１は炭素数１〜２０のアルキル基（該アルキル基はベンゼン環及び二重結合を含んでいてもよい。）、Ｘは−Ｏ−、−ＣＯＯ−あるいは−ＣＯＮＨ−であり、ｎは１〜３０の自然数であり、Ｙは水素原子、−ＣＨ２ＣＯＯＨを表す。（ただし、Ｘが−Ｏ−の場合は、イソシアネート官能基を有するシランカップリング剤は除く）｝
式（１）中の活性水素と反応可能な官能基を有するシランカップリング剤との反応生成物であることを特徴とする。
また、前記式（１）中の活性水素と反応可能な官能基を有するシランカップリング剤は、エポキシ基、イソシアネート基、酸無水物またはアミノ基のいずれかの官能基を有するシランカップリング剤であることを特徴とする。
更に、本発明の界面活性シランカップリング剤は、防曇剤の原料であることを特徴とする。この場合、防曇剤の原料となる界面活性シランカップリング剤は、前記式（１）中のＸが−Ｏ−の場合にイソシアネート官能基を有するシランカップリング剤であってもよい。
The surfactant silane coupling agent of the present invention is
A compound represented by the following formula (1) and R 1 —X— (CH 2 CH 2 O) n —Y (1)
{Wherein R 1 is an alkyl group having 1 to 20 carbon atoms (the alkyl group may include a benzene ring and a double bond), X is -O-, -COO- or -CONH-, n is a natural number of 1 to 30, and Y represents a hydrogen atom, —CH 2 COOH. (However, when X is —O—, the silane coupling agent having an isocyanate functional group is excluded.)}
It is a reaction product of a silane coupling agent having a functional group capable of reacting with active hydrogen in formula (1).
The silane coupling agent having a functional group capable of reacting with active hydrogen in the formula (1) is a silane coupling agent having any functional group of an epoxy group, an isocyanate group, an acid anhydride, or an amino group. It is characterized by being.
Furthermore, the surface active silane coupling agent of the present invention is a raw material for an antifogging agent. In this case, the surface active silane coupling agent as a raw material for the antifogging agent may be a silane coupling agent having an isocyanate functional group when X in the formula (1) is —O—.
本発明によれば、防曇効果が大きく、低コストで製造でき、コーティング可能な防曇剤の原料を提供することが出来る。 ADVANTAGE OF THE INVENTION According to this invention, the raw material of the anti-fogging agent which has a big anti-fogging effect, can be manufactured at low cost, and can be coated can be provided.
本発明において、界面活性シランカップリング剤は下記式（１）で表される化合物と
Ｒ１−Ｘ−（ＣＨ２ＣＨ２Ｏ）ｎ−Ｙ （１）
｛式中Ｒ１は炭素数１〜２０のアルキル基（該アルキル基はベンゼン環及び二重結合を含んでいてもよい）、Ｘは−Ｏ−、−ＣＯＯ−あるいは−ＣＯＮＨ−であり、ｎは１〜３０の自然数であり、Ｙは水素原子、−ＣＨ２ＣＯＯＨを表す｝
式（１）中の活性水素と反応可能な官能基を有するシランカップリング剤との反応生成物である（ただし、Ｘが−Ｏ−の場合は、イソシアネート官能基を有するシランカップリング剤は除く）。
In the present invention, the surface active silane coupling agent includes a compound represented by the following formula (1) and R 1 —X— (CH 2 CH 2 O) n —Y (1).
{Wherein R 1 is an alkyl group having 1 to 20 carbon atoms (the alkyl group may include a benzene ring and a double bond), X is —O—, —COO— or —CONH—, and n Is a natural number of 1-30, Y represents a hydrogen atom, —CH 2 COOH}
It is a reaction product of a silane coupling agent having a functional group capable of reacting with active hydrogen in formula (1) (however, when X is —O—, the silane coupling agent having an isocyanate functional group is excluded) ).
本発明の化合物の原料である前記式（１）で表される化合物は、Ｒ１の炭素数１〜２０のアルキレン基としては、メチル基、エチル基、オクチル基、デシル基、ドデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、パルミトレイル基、ヘプタデシル基、オクタデシル基、オレイル基等が挙げられる。これらのうち原料入手の点を考慮すると、好ましくは、メチル基、ドデシル基及びヘプタデシル基である。 The compound represented by the above formula (1), which is a raw material of the compound of the present invention, includes a methyl group, an ethyl group, an octyl group, a decyl group, a dodecyl group, tetradecyl as the alkylene group having 1 to 20 carbon atoms of R 1. Group, pentadecyl group, hexadecyl group, palmitoleyl group, heptadecyl group, octadecyl group, oleyl group and the like. Of these, considering the availability of raw materials, a methyl group, a dodecyl group, and a heptadecyl group are preferable.
Ｘは−Ｏ−、−ＣＯＯ−あるいは−ＣＯＮＨ−である。
ｎは１〜３０の自然数であり、原料入手の点から及び液体として取り扱い易い１〜９が好ましい。
Ｙは水素原子あるいは−ＣＨ２ＣＯＯＨである。
X is —O—, —COO— or —CONH—.
n is a natural number of 1 to 30 and is preferably 1 to 9 which is easy to handle as a liquid from the viewpoint of obtaining raw materials.
Y is a hydrogen atom or —CH 2 COOH.
前記一般式（１）で表される化合物は、界面活性剤であり、界面活性剤として市販されているものを使用することができる。
前記一般式（１）で表される化合物からなる界面活性剤で市販されているものは、通常エチレンオキサイドの付加数は一定でなく、その結果として単一なものでなく、エチレンオキサイドの付加数が異なった混合物として存在する。
前記式（１）で表される化合物の混合物であるの場合には、液体で取り扱いが容易な前記一般式（１）中のｎが平均で９以下であることが好ましい。
The compound represented by the general formula (1) is a surfactant, and those commercially available as surfactants can be used.
In the case of commercially available surfactants composed of the compound represented by the general formula (1), the addition number of ethylene oxide is usually not constant, and as a result, the addition number of ethylene oxide is not constant. Exist as different mixtures.
In the case of a mixture of compounds represented by the formula (1), it is preferable that n in the general formula (1) that is liquid and easy to handle is 9 or less on average.
式（１）で表される具体的な化合物としては以下の化合物が挙げられる。
ＣＨ３Ｏ（ＣＨ２ＣＨ２Ｏ）２Ｈ
ＣＨ３Ｏ（ＣＨ２ＣＨ２Ｏ）３Ｈ
ＣＨ３Ｏ（ＣＨ２ＣＨ２Ｏ）４Ｈ
ＣＨ３Ｏ（ＣＨ２ＣＨ２Ｏ）５Ｈ
ＣＨ３Ｏ（ＣＨ２ＣＨ２Ｏ）６Ｈ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）３ＣＨ２ＣＯＯＨ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）４ＣＨ２ＣＯＯＨ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）５ＣＨ２ＣＯＯＨ
Ｃ１３Ｈ２７Ｏ（ＣＨ２ＣＨ２Ｏ）３ＣＨ２ＣＯＯＨ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）７Ｈ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）８Ｈ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）９Ｈ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）１０Ｈ
Ｃ１２Ｈ２５Ｏ（ＣＨ２ＣＨ２Ｏ）１１Ｈ
Ｃ１７Ｈ３５ＣＯＯ（ＣＨ２ＣＨ２Ｏ）９Ｈ
Ｃ１７Ｈ３３ＣＯＯ（ＣＨ２ＣＨ２Ｏ）５Ｈ
Ｃ１７Ｈ３３ＣＯＯ（ＣＨ２ＣＨ２Ｏ）９Ｈ
Ｃ１７Ｈ３３ＣＯＯ（ＣＨ２ＣＨ２Ｏ）１４Ｈ
Ｃ１７Ｈ３５ＣＯＮＨＣＨ２ＣＨ２ＯＨ
Specific compounds represented by the formula (1) include the following compounds.
CH 3 O (CH 2 CH 2 O) 2 H
CH 3 O (CH 2 CH 2 O) 3 H
CH 3 O (CH 2 CH 2 O) 4 H
CH 3 O (CH 2 CH 2 O) 5 H
CH 3 O (CH 2 CH 2 O) 6 H
C 12 H 25 O (CH 2 CH 2 O) 3 CH 2 COOH
C 12 H 25 O (CH 2 CH 2 O) 4 CH 2 COOH
C 12 H 25 O (CH 2 CH 2 O) 5 CH 2 COOH
C 13 H 27 O (CH 2 CH 2 O) 3 CH 2 COOH
C 12 H 25 O (CH 2 CH 2 O) 7 H
C 12 H 25 O (CH 2 CH 2 O) 8 H
C 12 H 25 O (CH 2 CH 2 O) 9 H
C 12 H 25 O (CH 2 CH 2 O) 10 H
C 12 H 25 O (CH 2 CH 2 O) 11 H
C 17 H 35 COO (CH 2 CH 2 O) 9 H
C 17 H 33 COO (CH 2 CH 2 O) 5 H
C 17 H 33 COO (CH 2 CH 2 O) 9 H
C 17 H 33 COO (CH 2 CH 2 O) 14 H
C 17 H 35 CONHCH 2 CH 2 OH
前記式（１）で表される化合物中の活性水素と反応可能な官能基を有するシランカップリング剤は、エポキシ基、イソシアネート基、酸無水物基またはアミノ基のいずれかの官能基を有するシランカップリング剤である。 The silane coupling agent having a functional group capable of reacting with active hydrogen in the compound represented by the formula (1) is a silane having any functional group of an epoxy group, an isocyanate group, an acid anhydride group, or an amino group. It is a coupling agent.
そして、好ましい式（１）中の活性水素と反応可能なシランカップリング剤としては、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トリエトキシシラン、３-グリシドキシプロピルメチルジメトキシシラン、３-グリシドキシプロピルメチルジエトキシシラン、２-（３，４-エポキシシクロヘキシル）エチルトリメトキシシラン、３-イソシアネートプロピルトリエトキシシラン、３-トリメトキシシリルプロピルコハク酸無水物、３-アミノプロピルトリメトキシシラン及び３-アミノプロピルメチルジメトキシシラン等が挙げられる。 The preferable silane coupling agent capable of reacting with active hydrogen in the formula (1) is 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxy. Silane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-trimethoxysilylpropyl succinic anhydride, 3-amino And propyltrimethoxysilane and 3-aminopropylmethyldimethoxysilane.
式（１）で表される化合物と式（１）中の活性水素と反応可能な官能基を有するシランカップリング剤との反応で生成する本発明の具体的な化合物としては以下の化合物が挙げられる。
ＣＨ３−Ｏ−（ＣＨ２ＣＨ２Ｏ）３ＣＨ２ＣＨ（ＯＨ）ＣＨ２ＯＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
ＣＨ３−Ｏ−（ＣＨ２ＣＨ２Ｏ）３ＣＨ２ＣＨ（ＯＨ）ＣＨ２ＯＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＣＨ３）（ＯＣＨ３）２
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）７ＣＨ２ＣＨ（ＯＨ）ＣＨ２ＯＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）７ＣＨ２ＣＯＯＣＨ２ＣＨ（ＯＨ）ＣＨ２ＯＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）８ＣＨ２ＣＯＯＣＨ２ＣＨ（ＯＨ）ＣＨ２ＯＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）９ＣＨ２ＣＯＯＣＨ２ＣＨ（ＯＨ）ＣＨ２ＯＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）８ＣＨ２ＣＯＮＨＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）９ＣＨ２ＣＯＮＨＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
ＣＨ３−Ｏ−（ＣＨ２ＣＨ２Ｏ）３ＣＯＣＨ２ＣＨ（ＣＯＯＨ）ＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
ＣＨ３−Ｏ−（ＣＨ２ＣＨ２Ｏ）３ＣＯＣＨ（ＣＨ２ＣＯＯＨ）ＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）７ＣＯＣＨ２ＣＨ（ＣＯＯＨ）ＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１２Ｈ２５−Ｏ−（ＣＨ２ＣＨ２Ｏ）８ＣＯＣＨ（ＣＨ２ＣＯＯＨ）ＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１７Ｈ３５−ＣＯＯ−（ＣＨ２ＣＨ２Ｏ）９ＣＯＣＨ２ＣＨ（ＣＯＯＨ）ＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Ｃ１７Ｈ３３−ＣＯＯ−（ＣＨ２ＣＨ２Ｏ）５ＣＯＣＨ（ＣＨ２ＣＯＯＨ）ＣＨ２ＣＨ２ＣＨ２Ｓｉ（ＯＣＨ３）３
Specific compounds of the present invention produced by the reaction of the compound represented by the formula (1) and the silane coupling agent having a functional group capable of reacting with the active hydrogen in the formula (1) include the following compounds. It is done.
CH 3 -O- (CH 2 CH 2 O) 3 CH 2 CH (OH) CH 2 OCH 2 CH 2 CH 2 Si (OCH 3) 3
CH 3 -O- (CH 2 CH 2 O) 3 CH 2 CH (OH) CH 2 OCH 2 CH 2 CH 2 Si (CH 3) (OCH 3) 2
C 12 H 25 -O- (CH 2 CH 2 O) 7 CH 2 CH (OH) CH 2 OCH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 7 CH 2 COOCH 2 CH (OH) CH 2 OCH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 8 CH 2 COOCH 2 CH (OH) CH 2 OCH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 9 CH 2 COOCH 2 CH (OH) CH 2 OCH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 8 CH 2 CONHCH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 9 CH 2 CONHCH 2 CH 2 CH 2 Si (OCH 3) 3
CH 3 -O- (CH 2 CH 2 O) 3 COCH 2 CH (COOH) CH 2 CH 2 CH 2 Si (OCH 3) 3
CH 3 -O- (CH 2 CH 2 O) 3 COCH (CH 2 COOH) CH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 7 COCH 2 CH (COOH) CH 2 CH 2 CH 2 Si (OCH 3) 3
C 12 H 25 -O- (CH 2 CH 2 O) 8 COCH (CH 2 COOH) CH 2 CH 2 CH 2 Si (OCH 3) 3
C 17 H 35 -COO- (CH 2 CH 2 O) 9 COCH 2 CH (COOH) CH 2 CH 2 CH 2 Si (OCH 3) 3
C 17 H 33 -COO- (CH 2 CH 2 O) 5 COCH (CH 2 COOH) CH 2 CH 2 CH 2 Si (OCH 3) 3
本発明の化合物は以下の方法により得られる。
すなわち、式（１）で表される化合物と本発明で使用するシランカップリング剤を混合して、室温あるいは加熱下反応させることにより得られる。
The compound of the present invention can be obtained by the following method.
That is, it can be obtained by mixing the compound represented by the formula (1) and the silane coupling agent used in the present invention and reacting at room temperature or under heating.
式（１）で表される化合物と本発明で使用するシランカップリング剤の混合割合は、同等のモル比であればよいが、どちらか一方が過剰であっても良い。好ましくは、同じモル比か、シランカップリング剤を少し過剰にして反応させるのが好ましい。 The mixing ratio of the compound represented by the formula (1) and the silane coupling agent used in the present invention may be an equivalent molar ratio, but either one may be excessive. Preferably, the reaction is carried out at the same molar ratio or with a slight excess of the silane coupling agent.
反応温度は室温から２００℃であり、好ましくは室温から１００℃である。
必要により触媒を用いてもよい。
用いる触媒としては、一般式（１）で表される化合物末端が水酸基でシランカップリング剤がエポキシ基を有している場合、酸触媒（例えば、ｐ-トルエンスルホン酸や硫酸等）が挙げられる。
また、界面活性剤末端が水酸基でシランカップリング剤がイソシアネート基を有している場合、スズ系触媒（例えば、ジブチルスズジアセテートやジブチルスズジラウリエート等）やジルコニア系触媒（例えば、ジルコニウムテトラアセチルアセトネート等）等が挙げられる。
The reaction temperature is from room temperature to 200 ° C, preferably from room temperature to 100 ° C.
If necessary, a catalyst may be used.
Examples of the catalyst used include acid catalysts (for example, p-toluenesulfonic acid and sulfuric acid) when the compound represented by the general formula (1) has a hydroxyl group and the silane coupling agent has an epoxy group. .
Further, when the surfactant terminal is a hydroxyl group and the silane coupling agent has an isocyanate group, a tin-based catalyst (for example, dibutyltin diacetate or dibutyltin dilaurate) or a zirconia-based catalyst (for example, zirconium tetraacetylacetate). And the like).
溶媒は用いても用いなくてもよい。用いる溶媒としては、エーテル系溶媒（テトラハイドロフラン、ジオキサン及び１,２-ジメトキシエタン等）、芳香族系炭化水素（トルエン、キシレン等）、ケトン系溶媒（アセトン、メチルエチルケトン及びメチルイソブチルケトン等）及び非プロトン性溶媒（Ｎ，Ｎ-ジメチルホルムアミド、Ｎ，Ｎ-ジメチルアセトアミド、Ｎ-メチルピロリドン等）等が挙げられる。
これらのうち、無溶媒で行うのが好ましい。
A solvent may or may not be used. Solvents used include ether solvents (tetrahydrofuran, dioxane, 1,2-dimethoxyethane, etc.), aromatic hydrocarbons (toluene, xylene, etc.), ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.) and And aprotic solvents (N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, etc.).
Among these, it is preferable to carry out without solvent.
反応時間は、通常２〜７２時間であり、好ましくは８〜４８時間である。 The reaction time is usually 2 to 72 hours, preferably 8 to 48 hours.
本発明の界面活性シランカップリング剤は、防曇剤として用いることが出来る。この場合、防曇剤の原料となる界面活性シランカップリング剤は、前記式（１）中のＸが−Ｏ−の場合にイソシアネート官能基を有するシランカップリング剤であってもよい。
そして、前記界面活性シランカップリング剤を防曇剤として用いる場合、あらかじめ水溶性溶媒中で加水分解することが好ましい。
The surface active silane coupling agent of the present invention can be used as an antifogging agent. In this case, the surface active silane coupling agent as a raw material for the antifogging agent may be a silane coupling agent having an isocyanate functional group when X in the formula (1) is —O—.
And when using the said surface active silane coupling agent as an antifogging agent, it is preferable to hydrolyze in a water-soluble solvent previously.
用いる溶媒としては、アルコール系溶媒（メチルアルコール、エチルアルコール、イソプロピルアルコール及びｎ−ブチルアルコール等）、エーテル系溶媒（テトラハイドロフラン、ジオキサン及び１,２-ジメトキシエタン等）、芳香族系炭化水素（トルエン、キシレン等）、ケトン系溶媒（アセトン、メチルエチルケトン及びメチルイソブチルケトン等）及び非プロトン性溶媒（Ｎ，Ｎ-ジメチルホルムアミド、Ｎ，Ｎ-ジメチルアセトアミド、Ｎ-メチルピロリドン等）等が挙げられる。これらのうち好ましいのはアルコール系溶媒であり、特に好ましいのはメチルアルコール、エチルアルコール及びイソプロピルアルコールである。 Solvents used include alcohol solvents (methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol, etc.), ether solvents (tetrahydrofuran, dioxane, 1,2-dimethoxyethane, etc.), aromatic hydrocarbons ( Toluene, xylene, etc.), ketone solvents (acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.) and aprotic solvents (N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, etc.). Of these, alcohol solvents are preferable, and methyl alcohol, ethyl alcohol, and isopropyl alcohol are particularly preferable.
本発明の界面活性シランカップリング剤の量は、防曇剤に用いる溶媒に対して、０．００１〜２０重量％であり、好ましくは０．０１〜１０重量％である。 The amount of the surfactant silane coupling agent of the present invention is 0.001 to 20% by weight, preferably 0.01 to 10% by weight, based on the solvent used for the antifogging agent.
本発明の界面活性シランカップリング剤から誘導される防曇剤は、ガラス、プラスチック（ポリメチルメタクリレート、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート、ＡＢＳ、ポリカーボネート、ポリスチレン、エポキシ、不飽和ポリエステル、メラミン、ジアリルフタレート、ポリイミド、ウレタン、ナイロン、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリブタジエン、ポリイソプレン、ＳＢＲ、ニトリルラバー、ＥＰＭ、ＥＰＤＭ、エピクロルヒドリンラバー、ネオプレンラバー、ポルサルファイド及びブチルラバー等）、金属（鉄、アルミニウム、ステンレス、チタン、銅、黄銅及びこれらの合金等）、セルロース、セルロース誘導体、セルロース類似体（キチン、キトサン及びポルフィラン等）あるいは天然繊維（シルク及びコットン等）等の基板、シート、フィルム及び繊維の表面防曇化等に適用出来る。 Antifogging agents derived from the surfactant silane coupling agent of the present invention are glass, plastic (polymethyl methacrylate, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, ABS, polycarbonate, polystyrene, epoxy, unsaturated polyester, melamine Diallyl phthalate, polyimide, urethane, nylon, polyethylene, polypropylene, polyvinyl chloride, polybutadiene, polyisoprene, SBR, nitrile rubber, EPM, EPDM, epichlorohydrin rubber, neoprene rubber, porsulfide, butyl rubber, etc.), metal (iron, Aluminum, stainless steel, titanium, copper, brass and alloys thereof), cellulose, cellulose derivatives, cellulose analogs (chitin, chitosan and Substrate such Rufiran etc.) or natural fibers (silk and cotton, etc.), sheets, can be applied to the film and the surface antifogging, etc. of the fibers.
以下に実施例を示し、本発明を具体的に説明する。実施例は、本発明を説明するものであり、制限を加えるものではない。 Hereinafter, the present invention will be specifically described with reference to examples. The examples are illustrative of the invention and are not limiting.
〔実施例１〕
三洋化成工業株式会社製界面活性剤（ビューライトＬＣＡ−Ｈ、ポリオキシエチレンラウリルエーテル酢酸、酸価：１０７）７．５７ｇと３−グリシドキシプロピルトリメトキシシラン３．４ｇをアルゴン雰囲気下、１００℃で２日間反応させることにより、ビューライトＬＣＡ−Ｈと３−グリシドキシプロピルトリメトキシシランがエステル結合を介して結合した本発明の界面活性シランカップリング剤１０．３ｇを得た。１Ｈ−ＮＭＲ測定から原料である３−グリシドキシプロピルトリメトキシシランのエポキシ環上のプロトン（２．６２、２．８０、３．１６ｐｐｍ）の吸収が消失を確認した。
[Example 1]
Sanyo Kasei Kogyo Co., Ltd. surfactant (Burelite LCA-H, polyoxyethylene lauryl ether acetic acid, acid value: 107) 7.57 g and 3-glycidoxypropyltrimethoxysilane 3.4 g in an argon atmosphere, 100 By reacting at 2 ° C. for 2 days, 10.3 g of the surface active silane coupling agent of the present invention in which burite LCA-H and 3-glycidoxypropyltrimethoxysilane were bonded via an ester bond was obtained. From the 1 H-NMR measurement, it was confirmed that absorption of protons (2.62, 2.80, 3.16 ppm) on the epoxy ring of 3-glycidoxypropyltrimethoxysilane as a raw material disappeared.
〔実施例２〕
三洋化成工業株式会社製界面活性剤（エマルミンＬ−９０−Ｓ、ドデシルアルコールのエチレンオキサイド付加物、水酸基価：９８．３）２０．２ｇと３−グリシドキシプロピルトリメトキシシラン８．４ｇを、触媒としてｐ−トルエンスルホン酸０．１ｇを用い、アルゴン雰囲気下、１００℃で２日間反応させることにより、エマルミンＬ−９０−Ｓとグリシドキシプロピルトリメトキシシランがエーテル結合を介して結合した本発明の界面活性シランカップリング剤２８．１ｇを得た。１Ｈ−ＮＭＲ測定から原料である３−グリシドキシプロピルトリメトキシシランのエポキシ環上のプロトン（２．６２、２．８０、３．１６ｐｐｍ）の吸収が消失を確認した。
[Example 2]
Sanyo Chemical Industries, Ltd. surfactant (Emalmine L-90-S, ethylene oxide adduct of dodecyl alcohol, hydroxyl value: 98.3) 20.2 g and 3-glycidoxypropyltrimethoxysilane 8.4 g, A book in which emalmin L-90-S and glycidoxypropyltrimethoxysilane are bonded via an ether bond by using 0.1 g of p-toluenesulfonic acid as a catalyst and reacting at 100 ° C. for 2 days in an argon atmosphere. 28.1 g of the surface active silane coupling agent of the invention was obtained. From the 1 H-NMR measurement, it was confirmed that absorption of protons (2.62, 2.80, 3.16 ppm) on the epoxy ring of 3-glycidoxypropyltrimethoxysilane as a raw material disappeared.
〔比較例１〕
（１）３−（トリメトキシシリル）プロパン−１−チオール（チッソ株式会社）１５．０ｇ（７６．５ｍｍｏｌ）をエタノール３７５ｇに溶解させた後、オルガノシリカゾル（日産化学製、３０％イソプロパノール溶液、ＩＰＡ−ＳＴ）９０．０ｇ、水１００.０ｇを加え２４時間加熱還流した。冷却後過酸化水素水（三徳化学工業株式会社製、３０％水溶液）５２．５ｇ（４６３ｍｍｏｌ）を加え２４時間加熱還流した。反応終了後室温まで冷却後、水酸化リチウム１水和物３．２１ｇ（７６．５ｍｍｏｌ）を水１５ｇに溶かして加え中和し、さらに水を加えて７５０ｇに調整することにより、ＬｉＯＳＯ２−ＣＨ２ＣＨ２ＣＨ２Ｓｉ基で修飾されたシリカゾルを含む親水化剤を得た。
[Comparative Example 1]
(1) After dissolving 15.0 g (76.5 mmol) of 3- (trimethoxysilyl) propane-1-thiol (Chisso Corporation) in 375 g of ethanol, organosilica sol (Nissan Chemical, 30% isopropanol solution, IPA) -ST) 90.0 g and 100.0 g of water were added and the mixture was heated to reflux for 24 hours. After cooling, 52.5 g (463 mmol) of hydrogen peroxide (Santoku Chemical Co., Ltd., 30% aqueous solution) was added and heated to reflux for 24 hours. After completion of the reaction, after cooling to room temperature, 3.21 g (76.5 mmol) of lithium hydroxide monohydrate was dissolved in 15 g of water and neutralized, and further water was added to adjust to 750 g, whereby LiOSO 2 —CH 2. A hydrophilizing agent comprising a silica sol modified with 2 CH 2 CH 2 Si groups was obtained.
〔使用例１〕
（１）実施例１で得たケイ素系化合物１．０ｇをエタノール４８．０ｇに溶解させ、水１ｇを加えて一晩加熱還流させることにより、ケイ素系化合物が加水分解した化合物を含むエタノール溶液５０．０ｇを得た。
（２）比較例１の（１）で得たエタノール溶液２．５ｇ、使用例１の（１）で得たエタノール溶液１．０ｇをエタノール４６．５ｇに溶解させることにより本発明の界面活性シランカップリング剤から誘導される防曇剤を含むエタノール溶液５０．０ｇを得た。
[Usage example 1]
(1) An ethanol solution 50 containing a compound obtained by hydrolyzing a silicon compound by dissolving 1.0 g of the silicon compound obtained in Example 1 in 48.0 g of ethanol, adding 1 g of water, and heating and refluxing overnight. 0.0 g was obtained.
(2) The surfactant silane of the present invention is prepared by dissolving 2.5 g of the ethanol solution obtained in (1) of Comparative Example 1 and 1.0 g of the ethanol solution obtained in (1) of Use Example 1 in 46.5 g of ethanol. 50.0 g of an ethanol solution containing an antifogging agent derived from the coupling agent was obtained.
〔使用例２〕
（１）実施例２で得たケイ素系化合物１．０ｇをエタノール４８．０ｇに溶解させ、水１ｇを加えて一晩加熱還流させることにより、ケイ素系化合物が加水分解した化合物を含むエタノール溶液５０．０ｇを得た。
（２）比較例１の（１）で得たエタノール溶液２．５ｇ、使用例２の（１）で得たエタノール溶液１．０ｇをエタノール４６．５ｇに溶解させることにより本発明の界面活性シランカップリング剤から誘導される防曇剤を含むエタノール溶液５０．０ｇを得た。
[Usage example 2]
(1) An ethanol solution 50 containing a compound obtained by hydrolyzing a silicon compound by dissolving 1.0 g of the silicon compound obtained in Example 2 in 48.0 g of ethanol, adding 1 g of water, and heating and refluxing overnight. 0.0 g was obtained.
(2) The surfactant silane of the present invention is prepared by dissolving 2.5 g of the ethanol solution obtained in (1) of Comparative Example 1 and 1.0 g of the ethanol solution obtained in (1) of Use Example 2 in 46.5 g of ethanol. 50.0 g of an ethanol solution containing an antifogging agent derived from the coupling agent was obtained.
〔使用例３〕
（１）３，５−ジメチルピラゾール４．８１ｇ（５０．０ｍｍｏｌ）と３−イソシアナートプロピルトリエトキシシラン１２．３５ｇ（５０．０ｍｍｏｌ）を室温で３日間撹拌することにより３−イソシアナートプロピルトリエトキシシランのイソシアナート基を３，５−ジメチルピラゾールでブロックしたブロックドイソシアナート化合物１６．８ｇを得た。１Ｈ−ＮＭＲ測定から原料である３−（トリエトキシシリル）プロピルイソシアネートのイソシアネート基が結合した炭素のプロトン（３．２７〜３．３２ｐｐｍ）の吸収が消失して、新たに目的物のウレア基が結合した炭素のプロトン（３．３２〜３．３９ｐｐｍ）の吸収を確認した。
（２）比較例１の（１）で得たＬｉＯＳＯ２−ＣＨ２ＣＨ２ＣＨ２Ｓｉ（−Ｏ−）３基で修飾されたシリカゾルを含むエタノール溶液４９．０ｇに（１）で得たブロックドイソシアナート化合物１．０ｇを加えて室温で３日間撹拌することにより、ＬｉＯＳＯ２−ＣＨ２ＣＨ２ＣＨ２Ｓｉ（−Ｏ−）３基とブロックドイソシアナート基で修飾されたシリカゾルを含むエタノール溶液５０．０ｇを得た。
（３）比較例１の（１）で得たＬｉＯＳＯ２−ＣＨ２ＣＨ２ＣＨ２Ｓｉ（−Ｏ−）３基で修飾されたイソプロパノールシリカゾルを含むエタノール溶液４９．０ｇに３−（トリメトキシシリル）プロパン−１−チオール（チッソ株式会社）１．０ｇを加えて室温で３日間撹拌することにより、ＬｉＯＳＯ２−ＣＨ２ＣＨ２ＣＨ２Ｓｉ（−Ｏ−）３基とチオール基で修飾されたシリカゾルを含むエタノール溶液５０．０ｇを得た。
（４）３−（トリメトキシシリル）プロパン−１−チオール（チッソ株式会社）３．０ｇ（１５．３ｍｍｏｌ）及び実施例２の（１）で得た化合物１．２ｇをエタノール８０ｇに溶解させた後、オルガノシリカゾル（日産化学製、３０％イソプロパノール溶液、ＩＰＡ−ＳＴ）１８．０ｇ、水１９．５ｇを加え２４時間加熱還流した。冷却後過酸化水素水（三徳化学工業株式会社製、３０％水溶液）１０．５ｇ（４６３ｍｍｏｌ）を加え２４時間加熱還流した。反応終了後室温まで冷却後、水酸化リチウム１水和物０．９７ｇ（２７．９ｍｍｏｌ）を水１２．０ｇに溶かして加えて中和し、さらに水を加えて１５０．０ｇに調整することにより、ドデシルアルコールのエチレンオキサイド付加物基とＬｉＯＳＯ２−ＣＨ２ＣＨ２ＣＨ２Ｓｉ基で修飾されたシリカゾルを含むエタノール溶液１５０．０ｇを得た。
（５）（２）で得たエタノール溶液２．５ｇ、（３）で得たエタノール溶液２．５ｇ及び（４）で得たエタノール溶液５．０ｇをエタノール４０ｇに溶解させ、一晩加熱還流することにより本発明の界面活性シランカップリング剤から誘導される防曇剤を含むエタノール溶液５０．０ｇを得た。
[Usage example 3]
(1) 3, isocyanatopropyltriethoxy by stirring 4.81 g (50.0 mmol) of 3,5-dimethylpyrazole and 12.35 g (50.0 mmol) of 3-isocyanatopropyltriethoxysilane at room temperature for 3 days 16.8 g of a blocked isocyanate compound in which the isocyanate group of silane was blocked with 3,5-dimethylpyrazole was obtained. Absorption of carbon protons (3.27 to 3.32 ppm) to which the isocyanate group of 3- (triethoxysilyl) propyl isocyanate, which is a raw material, was bonded disappeared from 1 H-NMR measurement, and a new urea group of the target product was newly obtained. The absorption of protons (3.32 to 3.39 ppm) of carbon bonded to was confirmed.
(2) The block obtained in (1) in 49.0 g of an ethanol solution containing silica sol modified with 3 groups of LiOSO 2 —CH 2 CH 2 CH 2 Si (—O—) obtained in (1) of Comparative Example 1 Ethanol containing silica sol modified with 3 groups of LiOSO 2 —CH 2 CH 2 CH 2 Si (—O—) 3 and blocked isocyanate groups by adding 1.0 g of a doisocyanate compound and stirring at room temperature for 3 days 50.0 g of solution was obtained.
(3) 3- (trimethoxysilyl) was added to 49.0 g of an ethanol solution containing isopropanol silica sol modified with 3 groups of LiOSO 2 —CH 2 CH 2 CH 2 Si (—O—) obtained in (1) of Comparative Example 1. ) Modified with LiOSO 2 —CH 2 CH 2 CH 2 Si (—O—) 3 group and thiol group by adding 1.0 g of propane-1-thiol (Chisso Corporation) and stirring at room temperature for 3 days An ethanol solution containing 50.0 g of silica sol was obtained.
(4) 3.0 g (15.3 mmol) of 3- (trimethoxysilyl) propane-1-thiol (Chisso Corporation) and 1.2 g of the compound obtained in Example 1 (1) were dissolved in 80 g of ethanol. Thereafter, 18.0 g of organosilica sol (manufactured by Nissan Chemical Industries, 30% isopropanol solution, IPA-ST) and 19.5 g of water were added and heated to reflux for 24 hours. After cooling, 10.5 g (463 mmol) of hydrogen peroxide solution (manufactured by Santoku Chemical Co., Ltd., 30% aqueous solution) was added and heated to reflux for 24 hours. By cooling to room temperature after completion of the reaction, 0.97 g (27.9 mmol) of lithium hydroxide monohydrate was dissolved in 12.0 g of water and neutralized, and further water was added to adjust to 150.0 g. Then, 150.0 g of an ethanol solution containing silica sol modified with an ethylene oxide adduct group of dodecyl alcohol and a LiOSO 2 —CH 2 CH 2 CH 2 Si group was obtained.
(5) Dissolve 2.5 g of the ethanol solution obtained in (2), 2.5 g of the ethanol solution obtained in (3), and 5.0 g of the ethanol solution obtained in (4) in 40 g of ethanol, and heat to reflux overnight. As a result, 50.0 g of an ethanol solution containing an antifogging agent derived from the surfactant silane coupling agent of the present invention was obtained.
〔使用例４〕
（１）使用例２の（１）で得たエタノール溶液５．０ｇ、使用例３の（１）で得たブロックドイソシアネート化合物０．０５ｇをエタノール４３．９５ｇに溶解させ、水１．０ｇを加えて一晩加熱還流させることにより本発明の界面活性シランカップリング剤から誘導される防曇剤を含むエタノール溶液５０．０ｇを得た。
[Usage example 4]
(1) 5.0 g of the ethanol solution obtained in (1) of Use Example 2 and 0.05 g of the blocked isocyanate compound obtained in (1) of Use Example 3 were dissolved in 43.95 g of ethanol, and 1.0 g of water was dissolved. In addition, by heating and refluxing overnight, 50.0 g of an ethanol solution containing an antifogging agent derived from the surfactant silane coupling agent of the present invention was obtained.
防曇性評価結果
比較例１及び使用例１〜５で得た防曇剤で以下の様に所定の基板の表面を改質し、７０℃の温水浴上部に基板を置いて防曇性能（水蒸気による曇りの有無）を評価した。結果を表１に示した。
（比較例１、使用例１及び２：スライドガラス、使用例３及び４：ポリカーボネート）
Antifogging evaluation results The surface of a predetermined substrate was modified with the antifogging agent obtained in Comparative Example 1 and Use Examples 1 to 5 as follows, and the substrate was placed on the upper part of a 70 ° C hot water bath to prevent the antifogging performance ( The presence or absence of fogging with water vapor was evaluated. The results are shown in Table 1.
(Comparative Example 1, Use Examples 1 and 2: Slide glass, Use Examples 3 and 4: Polycarbonate)
（１）スライドガラス｛７６ｍｍ、２６ｍｍ、１．２ｍｍ；水酸化ナトリウムの２−プロパノール飽和溶液に２４時間浸漬した後、水洗し、乾燥（６０℃、２時間）したもの｝を処理液（表面防曇剤）に浸漬し、スライドガラスを取り出した後、液切りをし、１２０℃、１間加熱処理して表面防曇スライドガラスを得た。
（２）ポリカーボネート板{７６ｍｍ、２６ｍｍ、１．０ｍｍ；エタノールで洗浄したもの｝を処理液（表面防曇剤）に浸漬し、ポリカーボネート板を取り出した後、液切りをし、１３０℃、１間加熱処理した表面防曇ポリカーボネート板を得た。
(1) Slide glass {76 mm, 26 mm, 1.2 mm; immersed in 2-propanol saturated solution of sodium hydroxide for 24 hours, washed with water and dried (60 ° C., 2 hours)} After immersing in (fogging agent) and taking out the slide glass, it was drained and heat-treated at 120 ° C. for 1 hour to obtain a surface antifogging slide glass.
(2) A polycarbonate plate {76 mm, 26 mm, 1.0 mm; washed with ethanol} is immersed in a treatment solution (surface antifogging agent), taken out of the polycarbonate plate, drained, and at 130 ° C. for 1 to A heat-treated surface antifogging polycarbonate plate was obtained.
上記結果から明らかの様に本発明の界面活性シランカップリング剤を添加した系においては、防曇性を示すことが明らかである。 As is clear from the above results, the system to which the surface active silane coupling agent of the present invention is added clearly shows antifogging properties.
本発明の界面活性シランカップリング剤から誘導される防曇剤は、ガラスやプラスチックなどに対して防曇効果が大きいため、ガラス、メガネレンズ、光学レンズ、ミラー等の曇り防止剤（防曇剤）が大きく、コーティング可能で安価に製造出来るため、防曇剤のみならず、親水化剤、帯電防止剤、親水性コーティング組成物、抗菌剤、導電性、イオン（プロトン）伝導として好適である。
The antifogging agent derived from the surface-active silane coupling agent of the present invention has a large antifogging effect on glass, plastics and the like, and therefore antifogging agents (antifogging agents) for glass, eyeglass lenses, optical lenses, mirrors, etc. ) Is large, can be coated and can be manufactured at low cost, and is suitable not only as an antifogging agent but also as a hydrophilizing agent, an antistatic agent, a hydrophilic coating composition, an antibacterial agent, conductivity, and ionic (proton) conduction.
Claims (3)
Ｒ１−Ｘ−（ＣＨ２ＣＨ２Ｏ）ｎ−Ｙ （１）
｛式中Ｒ１は炭素数１〜２０のアルキル基（該アルキル基はベンゼン環及び二重結合を含んでいてもよい。）、Ｘは−Ｏ−、−ＣＯＯ−あるいは−ＣＯＮＨ−であり、ｎは１〜３０の自然数であり、Ｙは水素原子、−ＣＨ２ＣＯＯＨを表す。（ただし、Ｘが−Ｏ−の場合は、イソシアネート官能基を有するシランカップリング剤は除く）｝
式（１）中の活性水素と反応可能な官能基を有するシランカップリング剤との反応生成物であることを特徴とする界面活性シランカップリング剤。 A compound represented by the following formula (1) and R 1 —X— (CH 2 CH 2 O) n —Y (1)
{Wherein R 1 is an alkyl group having 1 to 20 carbon atoms (the alkyl group may include a benzene ring and a double bond), X is -O-, -COO- or -CONH-, n is a natural number of 1 to 30, and Y represents a hydrogen atom, —CH 2 COOH. (However, when X is —O—, the silane coupling agent having an isocyanate functional group is excluded.)}
A surface-active silane coupling agent, which is a reaction product of a silane coupling agent having a functional group capable of reacting with active hydrogen in formula (1).
Ｒ１−Ｘ−（ＣＨ２ＣＨ２Ｏ）ｎ−Ｙ （１）
｛式中Ｒ１は炭素数１〜２０のアルキル基（該アルキル基はベンゼン環及び二重結合を含んでいてもよい。）、Ｘは−Ｏ−、−ＣＯＯ−あるいは−ＣＯＮＨ−であり、ｎは１〜３０の自然数であり、Ｙは水素原子、−ＣＨ２ＣＯＯＨを表す。｝
式（１）中の活性水素と反応可能な官能基を有するシランカップリング剤との反応生成物であることを特徴とする防曇剤原料。 A compound represented by the following formula (1) and R 1 —X— (CH 2 CH 2 O) n —Y (1)
{Wherein R 1 is an alkyl group having 1 to 20 carbon atoms (the alkyl group may include a benzene ring and a double bond), X is -O-, -COO- or -CONH-, n is a natural number of 1 to 30, and Y represents a hydrogen atom, —CH 2 COOH. }
An antifogging agent raw material which is a reaction product of a silane coupling agent having a functional group capable of reacting with active hydrogen in formula (1).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015187643 | 2015-09-25 | ||
| JP2015187643 | 2015-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2017061439A true JP2017061439A (en) | 2017-03-30 |
Family
ID=58429902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015200702A Pending JP2017061439A (en) | 2015-09-25 | 2015-10-09 | Surface active silane coupling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2017061439A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116290553A (en) * | 2023-02-01 | 2023-06-23 | 杰森石膏板（嘉兴）有限公司 | Thermal insulation paper gypsum board |
Citations (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258477A (en) * | 1963-07-19 | 1966-06-28 | Dow Corning | Acryloxyalkylsilanes and compositions thereof |
| JPS5455455A (en) * | 1977-10-12 | 1979-05-02 | Toyo Contact Lens Co Ltd | Contact lens |
| JPS5515110A (en) * | 1978-07-15 | 1980-02-02 | Toyo Contact Lens Co Ltd | Contact lens |
| EP0101027A1 (en) * | 1982-08-18 | 1984-02-22 | Herbert Prof. Dr. Rupprecht | Organic compounds bonded to SiO2, process for preparing them and their use |
| JPH05331455A (en) * | 1992-05-29 | 1993-12-14 | Shin Etsu Chem Co Ltd | Hydrophilic oil-repellent treating agent |
| JP2000191730A (en) * | 1998-12-24 | 2000-07-11 | Toray Ind Inc | Monomer for ophthalmic lens, polymer for ophthalmic lens and contact lens using the same |
| JP2000191667A (en) * | 1998-12-24 | 2000-07-11 | Toray Ind Inc | Monomer for lens for eye, polymer for lens for eye, and contact lens using the same |
| JP2000290536A (en) * | 1999-04-09 | 2000-10-17 | Daikin Ind Ltd | Aqueous coating resin composition |
| KR20110099984A (en) * | 2010-03-03 | 2011-09-09 | 사회복지법인 삼성생명공익재단 | Novel ligand for preparing molecular imaging probe, molecular imaging probe comprising the ligand, molecular imaging particle comprising the imaging probe, and a process for the preparation thereof, and a pharmaceutical composition comprising the same |
| EP2474577A1 (en) * | 2011-01-10 | 2012-07-11 | Samsung Electronics Co., Ltd. | Composition for coating film to prevent conspicuous fingerprints, coating film to prevent conspicuous fingerprints using the composition, and article having the coating film |
| JP2012232904A (en) * | 2011-04-28 | 2012-11-29 | National Institute Of Advanced Industrial Science & Technology | Methoxy oligoethyleneglycol-silane compound surface modification material |
| JP2012240983A (en) * | 2011-05-23 | 2012-12-10 | National Institute Of Advanced Industrial Science & Technology | Surface modification material for immobilizing protein |
| WO2013127772A1 (en) * | 2012-03-01 | 2013-09-06 | Wacker Chemie Ag | Molded parts having hydrophilic surfaces |
| WO2013127775A1 (en) * | 2012-03-01 | 2013-09-06 | Wacker Chemie Ag | Organosilicon compounds and the use thereof for producing hydrophilic surfaces |
| JP2014513660A (en) * | 2011-03-14 | 2014-06-05 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップ | Modified silica particles |
| JP2015516471A (en) * | 2012-03-01 | 2015-06-11 | ワッカー ケミー アクチエンゲゼルシャフトＷａｃｋｅｒ Ｃｈｅｍｉｅ ＡＧ | Crosslinkable composition based on organosilicon compounds |
| WO2016083310A1 (en) * | 2014-11-24 | 2016-06-02 | Sika Technology Ag | Polymer containing silane groups |
| WO2016083311A1 (en) * | 2014-11-24 | 2016-06-02 | Sika Technology Ag | Hydroxy silane as an adhesion promoter or cross-linking agent |
| JP2016114357A (en) * | 2014-12-10 | 2016-06-23 | 学校法人日本大学 | Abo type blood back inspection device, and optical abo type blood back inspection method |
| JP2017527630A (en) * | 2014-09-16 | 2017-09-21 | クロノス セラピュイティック リミテッド | For example, 2- [bis (4-fluorophenyl) methyl] -2,7-diazaspiro [4.5] decane as an inhibitor of human dopamine activity transporter (DAT) protein for the treatment of attention deficit disorder (ADD) -10-one derivatives and related compounds |
| JP2017527769A (en) * | 2014-10-02 | 2017-09-21 | ローベルト ボッシュ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Glow pin plug |
-
2015
- 2015-10-09 JP JP2015200702A patent/JP2017061439A/en active Pending
Patent Citations (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3258477A (en) * | 1963-07-19 | 1966-06-28 | Dow Corning | Acryloxyalkylsilanes and compositions thereof |
| JPS5455455A (en) * | 1977-10-12 | 1979-05-02 | Toyo Contact Lens Co Ltd | Contact lens |
| JPS5515110A (en) * | 1978-07-15 | 1980-02-02 | Toyo Contact Lens Co Ltd | Contact lens |
| EP0101027A1 (en) * | 1982-08-18 | 1984-02-22 | Herbert Prof. Dr. Rupprecht | Organic compounds bonded to SiO2, process for preparing them and their use |
| JPH05331455A (en) * | 1992-05-29 | 1993-12-14 | Shin Etsu Chem Co Ltd | Hydrophilic oil-repellent treating agent |
| JP2000191730A (en) * | 1998-12-24 | 2000-07-11 | Toray Ind Inc | Monomer for ophthalmic lens, polymer for ophthalmic lens and contact lens using the same |
| JP2000191667A (en) * | 1998-12-24 | 2000-07-11 | Toray Ind Inc | Monomer for lens for eye, polymer for lens for eye, and contact lens using the same |
| JP2000290536A (en) * | 1999-04-09 | 2000-10-17 | Daikin Ind Ltd | Aqueous coating resin composition |
| KR20110099984A (en) * | 2010-03-03 | 2011-09-09 | 사회복지법인 삼성생명공익재단 | Novel ligand for preparing molecular imaging probe, molecular imaging probe comprising the ligand, molecular imaging particle comprising the imaging probe, and a process for the preparation thereof, and a pharmaceutical composition comprising the same |
| EP2474577A1 (en) * | 2011-01-10 | 2012-07-11 | Samsung Electronics Co., Ltd. | Composition for coating film to prevent conspicuous fingerprints, coating film to prevent conspicuous fingerprints using the composition, and article having the coating film |
| JP2014513660A (en) * | 2011-03-14 | 2014-06-05 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップ | Modified silica particles |
| JP2012232904A (en) * | 2011-04-28 | 2012-11-29 | National Institute Of Advanced Industrial Science & Technology | Methoxy oligoethyleneglycol-silane compound surface modification material |
| JP2012240983A (en) * | 2011-05-23 | 2012-12-10 | National Institute Of Advanced Industrial Science & Technology | Surface modification material for immobilizing protein |
| WO2013127772A1 (en) * | 2012-03-01 | 2013-09-06 | Wacker Chemie Ag | Molded parts having hydrophilic surfaces |
| WO2013127775A1 (en) * | 2012-03-01 | 2013-09-06 | Wacker Chemie Ag | Organosilicon compounds and the use thereof for producing hydrophilic surfaces |
| JP2015516471A (en) * | 2012-03-01 | 2015-06-11 | ワッカー ケミー アクチエンゲゼルシャフトＷａｃｋｅｒ Ｃｈｅｍｉｅ ＡＧ | Crosslinkable composition based on organosilicon compounds |
| JP2017527630A (en) * | 2014-09-16 | 2017-09-21 | クロノス セラピュイティック リミテッド | For example, 2- [bis (4-fluorophenyl) methyl] -2,7-diazaspiro [4.5] decane as an inhibitor of human dopamine activity transporter (DAT) protein for the treatment of attention deficit disorder (ADD) -10-one derivatives and related compounds |
| JP2017527769A (en) * | 2014-10-02 | 2017-09-21 | ローベルト ボッシュ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Glow pin plug |
| WO2016083310A1 (en) * | 2014-11-24 | 2016-06-02 | Sika Technology Ag | Polymer containing silane groups |
| WO2016083311A1 (en) * | 2014-11-24 | 2016-06-02 | Sika Technology Ag | Hydroxy silane as an adhesion promoter or cross-linking agent |
| JP2016114357A (en) * | 2014-12-10 | 2016-06-23 | 学校法人日本大学 | Abo type blood back inspection device, and optical abo type blood back inspection method |
Non-Patent Citations (4)
| Title |
|---|
| J. AM. CHEM. SOC., vol. １３５, JPN6019015557, 2013, pages 4079 - 4087, ISSN: 0004026086 * |
| LANGMUIR, vol. ２９, JPN6019015554, 2013, pages 13111 - 13120, ISSN: 0004026085 * |
| PAPERS PRESENTED AT THE MEETING - AMERICAN CHEMICAL SOCIETY. DIVISION OF POLYMER CHEMISTRY, vol. ２４, JPN6019015565, 1983, pages 196 - 197, ISSN: 0004026088 * |
| SENSORS AND ACTUATORS B, vol. １３４, JPN6019015562, 2008, pages 672 - 679, ISSN: 0004026087 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116290553A (en) * | 2023-02-01 | 2023-06-23 | 杰森石膏板（嘉兴）有限公司 | Thermal insulation paper gypsum board |
| CN116290553B (en) * | 2023-02-01 | 2024-04-19 | 杰森新材料有限公司 | Thermal insulation paper gypsum board |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPWO2016167097A1 (en) | Betaine silicon compound, method for producing the same, hydrophilic coating composition liquid and coating film | |
| JP5750436B2 (en) | Modified metal oxide sol | |
| US20120128930A1 (en) | Method for Attachment of Silicon-Containing Compounds to a Surface and for Synthesis of Hypervalent Silicon-Compounds | |
| KR20130124165A (en) | Antimicrobial coatings | |
| US10377777B2 (en) | Anti-fogging agent | |
| US20200362213A1 (en) | Anti-fogging agent | |
| JP6291820B2 (en) | Silyl group-containing phosphorylcholine compound, method for producing the same, polycondensate and surface modifier | |
| JP2015013983A (en) | Surface modifier and article | |
| TWI805569B (en) | Water-repellent structure and manufacturing method thereof | |
| US20220127418A1 (en) | Fluoropolyether group-containing silane compound | |
| JP2017061439A (en) | Surface active silane coupling agent | |
| CN113045970B (en) | Coating composition and coated article | |
| JP6531124B2 (en) | Method for producing sulfobetaine-based silicon compound | |
| JP2014009307A (en) | Antistat | |
| JP2018135299A (en) | Amine oxide-based silicon compound and method for producing the same | |
| JP2005105045A (en) | Surfactant composition | |
| JP2005089705A (en) | Sulfonic acid group-containing ladder silicone and composition | |
| KR101915283B1 (en) | Antifouling coating agent and antifouling coating thereof | |
| JP2021098834A (en) | Hydrophilizing agent composition | |
| JP4411515B2 (en) | Fluorosurfactant | |
| JP5840930B2 (en) | Method for producing modified metal oxide sol | |
| JP2004529244A5 (en) | ||
| JP3577285B2 (en) | New coating agent | |
| JP2021046355A (en) | Antibacterial hydrophilizing agent | |
| JP5608421B2 (en) | Sulfur-containing silicon compound, production method thereof, condensate thereof, surface treatment agent and coating product |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151016 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180322 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190528 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20191224 |