WO2023100991A1 - シルセスキオキサン誘導体、硬化性組成物、ハードコート剤、硬化物、ハードコート及び基材 - Google Patents
シルセスキオキサン誘導体、硬化性組成物、ハードコート剤、硬化物、ハードコート及び基材 Download PDFInfo
- Publication number
- WO2023100991A1 WO2023100991A1 PCT/JP2022/044462 JP2022044462W WO2023100991A1 WO 2023100991 A1 WO2023100991 A1 WO 2023100991A1 JP 2022044462 W JP2022044462 W JP 2022044462W WO 2023100991 A1 WO2023100991 A1 WO 2023100991A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- carbon atoms
- meth
- silsesquioxane derivative
- structural unit
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 84
- 239000000463 material Substances 0.000 title description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 125000000962 organic group Chemical group 0.000 claims abstract description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 98
- 239000011248 coating agent Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 239000003505 polymerization initiator Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 abstract 1
- 125000006585 (C6-C10) arylene group Chemical group 0.000 abstract 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- -1 polysiloxane Polymers 0.000 description 68
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 50
- 150000003377 silicon compounds Chemical class 0.000 description 37
- 150000001875 compounds Chemical class 0.000 description 36
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 35
- 239000000047 product Substances 0.000 description 29
- 238000001723 curing Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 21
- 238000000576 coating method Methods 0.000 description 21
- 229910052710 silicon Inorganic materials 0.000 description 20
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 9
- 239000000470 constituent Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000003566 oxetanyl group Chemical group 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- 229910000077 silane Inorganic materials 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000001678 irradiating effect Effects 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 4
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 3
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- ZXNBBWHRUSXUFZ-UHFFFAOYSA-N 3-methyl-2-pentanol Chemical compound CCC(C)C(C)O ZXNBBWHRUSXUFZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000001400 nonyl 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])[H] 0.000 description 2
- 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 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- 239000004306 orthophenyl phenol Substances 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- HCXVPNKIBYLBIT-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOOC(C)(C)C HCXVPNKIBYLBIT-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 1
- FYRCDEARNUVZRG-UHFFFAOYSA-N 1,1,5-trimethyl-3,3-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CC(C)CC(C)(C)C1 FYRCDEARNUVZRG-UHFFFAOYSA-N 0.000 description 1
- VBQCFYPTKHCPGI-UHFFFAOYSA-N 1,1-bis(2-methylpentan-2-ylperoxy)cyclohexane Chemical compound CCCC(C)(C)OOC1(OOC(C)(C)CCC)CCCCC1 VBQCFYPTKHCPGI-UHFFFAOYSA-N 0.000 description 1
- VTEYUPDBOLSXCD-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-2-methylcyclohexane Chemical compound CC1CCCCC1(OOC(C)(C)C)OOC(C)(C)C VTEYUPDBOLSXCD-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- OTMBZPVYOQYPBE-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclododecane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCCCCCCCC1 OTMBZPVYOQYPBE-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- KHKNFKNBERMAAR-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)N(CCO)C1=O KHKNFKNBERMAAR-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-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
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- YWEJNVNVJGORIU-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-hydroxy-2-phenylacetate Chemical compound OCCOCCOC(=O)C(O)C1=CC=CC=C1 YWEJNVNVJGORIU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- IEMBFTKNPXENSE-UHFFFAOYSA-N 2-(2-methylpentan-2-ylperoxy)propan-2-yl hydrogen carbonate Chemical compound CCCC(C)(C)OOC(C)(C)OC(O)=O IEMBFTKNPXENSE-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- XKBHBVFIWWDGQX-UHFFFAOYSA-N 2-bromo-3,3,4,4,5,5,5-heptafluoropent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Br)=C XKBHBVFIWWDGQX-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-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
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- BZGMEGUFFDTCNP-UHFFFAOYSA-N 2-hydroperoxy-2-methylpentane Chemical compound CCCC(C)(C)OO BZGMEGUFFDTCNP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-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
- ISTJMQSHILQAEC-UHFFFAOYSA-N 2-methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 description 1
- GQUHOPFCZGMERZ-UHFFFAOYSA-N 2-methyloxirane;2-nonylphenol Chemical class CC1CO1.CCCCCCCCCC1=CC=CC=C1O GQUHOPFCZGMERZ-UHFFFAOYSA-N 0.000 description 1
- WJORGWQDTVMZDR-UHFFFAOYSA-N 2-methyloxirane;phenol Chemical class CC1CO1.OC1=CC=CC=C1 WJORGWQDTVMZDR-UHFFFAOYSA-N 0.000 description 1
- WXDJDZIIPSOZAH-UHFFFAOYSA-N 2-methylpentan-2-yl benzenecarboperoxoate Chemical compound CCCC(C)(C)OOC(=O)C1=CC=CC=C1 WXDJDZIIPSOZAH-UHFFFAOYSA-N 0.000 description 1
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical class C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
- BQARUDWASOOSRH-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-yl hydrogen carbonate Chemical compound CC(C)(C)OOC(C)(C)OC(O)=O BQARUDWASOOSRH-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- FSRHFTKAMSLMBK-UHFFFAOYSA-N 3-[(3-ethyloxetan-3-yl)methoxy]propyl-trimethoxysilane Chemical compound CO[Si](OC)(OC)CCCOCC1(CC)COC1 FSRHFTKAMSLMBK-UHFFFAOYSA-N 0.000 description 1
- AMZNFNXOVYDPBW-UHFFFAOYSA-N 3-[[dimethyl(3-prop-2-enoyloxypropyl)silyl]oxy-dimethylsilyl]propyl prop-2-enoate Chemical compound C=CC(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C=C AMZNFNXOVYDPBW-UHFFFAOYSA-N 0.000 description 1
- ZIFLDVXQTMSDJE-UHFFFAOYSA-N 3-[[dimethyl-[3-(2-methylprop-2-enoyloxy)propyl]silyl]oxy-dimethylsilyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(C)O[Si](C)(C)CCCOC(=O)C(C)=C ZIFLDVXQTMSDJE-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
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- MCDBEBOBROAQSH-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C=C MCDBEBOBROAQSH-UHFFFAOYSA-N 0.000 description 1
- JBDMKOVTOUIKFI-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(C)CCCOC(=O)C(C)=C JBDMKOVTOUIKFI-UHFFFAOYSA-N 0.000 description 1
- ZCRUJAKCJLCJCP-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(C)CCCOC(=O)C=C ZCRUJAKCJLCJCP-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- DOGMJCPBZJUYGB-UHFFFAOYSA-N 3-trichlorosilylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](Cl)(Cl)Cl DOGMJCPBZJUYGB-UHFFFAOYSA-N 0.000 description 1
- LEPRPXBFZRAOGU-UHFFFAOYSA-N 3-trichlorosilylpropyl prop-2-enoate Chemical compound Cl[Si](Cl)(Cl)CCCOC(=O)C=C LEPRPXBFZRAOGU-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-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
- 238000010146 3D printing Methods 0.000 description 1
- WLDMPODMCFGWAA-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)NC(=O)C21 WLDMPODMCFGWAA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- PRKPGWQEKNEVEU-UHFFFAOYSA-N 4-methyl-n-(3-triethoxysilylpropyl)pentan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC(C)C PRKPGWQEKNEVEU-UHFFFAOYSA-N 0.000 description 1
- GAYWTJPBIQKDRC-UHFFFAOYSA-N 8-trimethoxysilyloctyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCOC(=O)C(C)=C GAYWTJPBIQKDRC-UHFFFAOYSA-N 0.000 description 1
- JOVCTEPPTIOAPX-UHFFFAOYSA-N 8-trimethoxysilyloctyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCOC(=O)C=C JOVCTEPPTIOAPX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical class OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- MKGOQPZSFOPJIS-UHFFFAOYSA-N C(C)(=O)C1=CC=CC=C1.C(C1=CC=CC=C1)(=O)C1=CC=C(C=C1)SC1=CC=C(C=C1)C(C(C)(S(=O)C1=CC=C(C=C1)C)C)=O Chemical compound C(C)(=O)C1=CC=CC=C1.C(C1=CC=CC=C1)(=O)C1=CC=C(C=C1)SC1=CC=C(C=C1)C(C(C)(S(=O)C1=CC=C(C=C1)C)C)=O MKGOQPZSFOPJIS-UHFFFAOYSA-N 0.000 description 1
- DWADCHYAFJYRRZ-UHFFFAOYSA-N C(C)(C)C1=C(C=CC=C1)C(=O)C(O)C1=CC=CC=C1.C1(=CC=CC=C1)C(=O)C(O)C1=CC=CC=C1 Chemical class C(C)(C)C1=C(C=CC=C1)C(=O)C(O)C1=CC=CC=C1.C1(=CC=CC=C1)C(=O)C(O)C1=CC=CC=C1 DWADCHYAFJYRRZ-UHFFFAOYSA-N 0.000 description 1
- LLYFFVYNWOLVNE-UHFFFAOYSA-N C=CC(C1=CC=CC=C1)NC(CCN)CCCl Chemical compound C=CC(C1=CC=CC=C1)NC(CCN)CCCl LLYFFVYNWOLVNE-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229910000976 Electrical steel Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- UNKQAWPNGDCPTE-UHFFFAOYSA-N [2,5-dimethyl-5-(3-methylbenzoyl)peroxyhexan-2-yl] 3-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC(C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C=2C=C(C)C=CC=2)=C1 UNKQAWPNGDCPTE-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- FYABMGZBIRRBQY-UHFFFAOYSA-N benzene;hydrogen peroxide Chemical compound OO.C1=CC=CC=C1 FYABMGZBIRRBQY-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- GQVVQDJHRQBZNG-UHFFFAOYSA-N benzyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CC1=CC=CC=C1 GQVVQDJHRQBZNG-UHFFFAOYSA-N 0.000 description 1
- GSKAIYAPIGRGRZ-UHFFFAOYSA-N benzyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CC1=CC=CC=C1 GSKAIYAPIGRGRZ-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 description 1
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 1
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- PJIFJEUHCQYNHO-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCCN=C=O PJIFJEUHCQYNHO-UHFFFAOYSA-N 0.000 description 1
- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- SLQTWNAJXFHMHM-UHFFFAOYSA-N dimethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OC)OC)CCC2OC21 SLQTWNAJXFHMHM-UHFFFAOYSA-N 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- GOIPELYWYGMEFQ-UHFFFAOYSA-N dimethoxy-methyl-octylsilane Chemical compound CCCCCCCC[Si](C)(OC)OC GOIPELYWYGMEFQ-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- WQTNGCZMPUCIEX-UHFFFAOYSA-N dimethoxy-methyl-prop-2-enylsilane Chemical compound CO[Si](C)(OC)CC=C WQTNGCZMPUCIEX-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 description 1
- VEJBQZZDVYDUHU-UHFFFAOYSA-N ethenyl-hydroxy-dimethylsilane Chemical compound C[Si](C)(O)C=C VEJBQZZDVYDUHU-UHFFFAOYSA-N 0.000 description 1
- NUFVQEIPPHHQCK-UHFFFAOYSA-N ethenyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)C=C NUFVQEIPPHHQCK-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- MWCKAHGTDSPMKV-UHFFFAOYSA-N ethynyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C#C MWCKAHGTDSPMKV-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910001195 gallium oxide Inorganic materials 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical class OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical class Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical class OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- REQXNMOSXYEQLM-UHFFFAOYSA-N methoxy-dimethyl-phenylsilane Chemical compound CO[Si](C)(C)C1=CC=CC=C1 REQXNMOSXYEQLM-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- HMDRAGZZZBGZJC-UHFFFAOYSA-N n-[3-[3-aminopropoxy(dimethoxy)silyl]propyl]-1-phenylprop-2-en-1-amine Chemical compound NCCCO[Si](OC)(OC)CCCNC(C=C)C1=CC=CC=C1 HMDRAGZZZBGZJC-UHFFFAOYSA-N 0.000 description 1
- YZPARGTXKUIJLJ-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]aniline Chemical compound CO[Si](C)(OC)CCCNC1=CC=CC=C1 YZPARGTXKUIJLJ-UHFFFAOYSA-N 0.000 description 1
- DRRZZMBHJXLZRS-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]cyclohexanamine Chemical compound CO[Si](C)(OC)CCCNC1CCCCC1 DRRZZMBHJXLZRS-UHFFFAOYSA-N 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- 239000002135 nanosheet Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- VSXGXPNADZQTGQ-UHFFFAOYSA-N oxirane;phenol Chemical class C1CO1.OC1=CC=CC=C1 VSXGXPNADZQTGQ-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006350 polyacrylonitrile resin Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Chemical class [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010352 sodium erythorbate Nutrition 0.000 description 1
- 239000004320 sodium erythorbate Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical class [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical class [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- XTXFUQOLBKQKJU-UHFFFAOYSA-N tert-butylperoxy(trimethyl)silane Chemical compound CC(C)(C)OO[Si](C)(C)C XTXFUQOLBKQKJU-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000012546 transfer Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- GAMLUOSQYHLFCT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-3-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1(CC)COC1 GAMLUOSQYHLFCT-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
Definitions
- the present invention relates to silsesquioxane derivatives, curable compositions, hard coating agents, cured products, hard coatings and substrates.
- Hard coating agents are used in various places such as displays and housings that require hardness.
- Various curable compositions are known as compositions used for hard coating agents, and for example, polyfunctional acrylates are known.
- organic-inorganic composite compositions in which inorganic fillers are mixed with organic resins
- organic-inorganic hybrid materials in which organic units and inorganic units coexist or chemically bond in nano-order.
- silsesquioxane derivatives are known as such organic-inorganic hybrid materials.
- the applied curable composition is irradiated with an active energy ray such as ultraviolet rays and cured. known to do. If the substrate is in the form of a film, a roll-to-roll coating and curing method can be used. It is known that a nanoimprint method can also be applied to form the hard coat layer.
- Patent Document 1 discloses a composition for forming a hard coat layer containing a polyorganosilsesquioxane having a siloxane structural unit containing an oxetanyl group and a siloxane structural unit containing an epoxy group, and a polymerization initiator. disclosed.
- Patent Document 2 1 to 10 mol% of a dialkoxysilane containing at least one of an alkyl group having 1 to 12 carbon atoms and an aryl group having 6 to 20 carbon atoms and a trialkoxysilane containing a (meth)acrylic group
- a polysiloxane comprising 90 to 99 mol % of an alkoxysilane (provided that the sum of dialkoxysilane and trialkoxysilane is 100 mol %) and a hard coating composition containing the polysiloxane are disclosed.
- Patent Document 3 a polymerizable compound having a polymerizable functional group such as a (meth) acryloyl group and having a siloxane bond having a bifunctional silane as a constituent unit more than a trifunctional silane, and a photopolymerizable and an initiator.
- a polymerizable compound having a polymerizable functional group such as a (meth) acryloyl group and having a siloxane bond having a bifunctional silane as a constituent unit more than a trifunctional silane
- Patent Document 1 International Publication 2019/188441 Pamphlet
- Patent Document 2 Japanese Patent Application Laid-Open No. 2013-035918
- Patent Document 3 International Publication 2020/203472 Pamphlet
- curable compositions containing a silsesquioxane derivative or the like When applying a curable composition containing a silsesquioxane derivative or the like to a substrate, it is common to mix the curable composition and a solvent from the viewpoint of improving the coating properties of the curable composition. .
- the curable composition contains a solvent, it is necessary to remove the solvent before curing the coating film, and it is desirable to reduce the amount of solvent used from the viewpoint of reducing environmental load and energy consumption.
- curable compositions that are solvent-free (solvent-free systems) and have low viscosities.
- a solvent-free curable composition preferably has low viscosity, good applicability, curability, and the like, and the cured product obtained by curing the curable composition has high hardness.
- the curability of the curable composition and the hardness of the cured product obtained by curing the curable composition tend to decrease. Therefore, there is generally a trade-off relationship between the viscosity of the solvent-free curable composition, the curability of the curable composition, and the hardness of the cured product.
- Patent Literature 1 describes that a hard coat film was produced as follows. First, a polysilsesquioxane consisting only of T units (units having 3 O 1/2 per silicon atom) obtained by hydrolyzing and polycondensing a trifunctional silane, and a photopolymerization initiator and using methyl isobutyl ketone (MIBK) as a solvent and applying a photocurable composition having a solid concentration of 50% to a substrate. Thereafter, the coating film is heated to remove the solvent, then irradiated with ultraviolet rays, and further heated to cure the coating film, thereby producing a hard coat film having a hard coat layer.
- MIBK methyl isobutyl ketone
- a hard coat containing polysilsesquioxane consisting of only T units as described in Patent Document 1 has high hardness.
- Patent Document 2 describes that a coating film was produced as follows. First, D units obtained by hydrolyzing and polycondensing a dialkoxysilane and a trialkoxysilane containing a (meth)acrylic group (units having two O 1/2 per silicon atom) and A solvent-diluted photocurable composition is prepared comprising a polysiloxane having T units and a photoinitiator. After applying the prepared photocurable composition to a substrate, it is pre-baked, and then a coating film is produced using a high-pressure mercury lamp. A cured coating film using such a silsesquioxane derivative consisting of D units and T units may have low hardness.
- Patent Document 3 describes that a pattern was formed on a base material as follows. First, (1) a polymerizable compound having a siloxane bond having more structural units of a bifunctional silane than a trifunctional silane, and (2) a siloxane bond having more structural units of a bifunctional silane than a trifunctional silane. or (3) a polymerizable compound obtained by reacting a polymerizable compound obtained from a trifunctional silane with chlorotrimethylsilane. and a photopolymerization initiator. A solvent-free photocurable resin composition for imprinting is applied onto a quartz base material, and while being in contact with a quartz imprinting mold, is irradiated with light to produce a photocurable resin composition for imprinting.
- Patent Document 3 when the polymerizable compound described in (1) or (2) above is used, the hardness of the cured product may decrease, and the polymerizable compound described in (3) above may is used, the viscosity is high, and there is room for improvement in that it can be used without a solvent.
- the present invention has been made in view of the above, a silsesquioxane derivative capable of producing a cured product having a low viscosity and excellent hardness, a curable composition containing the silsesquioxane derivative, and the , a hard coating agent containing the silsesquioxane derivative, a hard coating obtained by curing the same, and a substrate containing the hard coating.
- Means for solving the above problems include the following aspects. ⁇ 1> A silsesquioxane derivative represented by the following formula (1).
- R 1 and R 2 are each independently an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 10 carbon atoms, an arylene group having 6 to 10 carbon atoms, or a number of carbon atoms.
- R 3 is an alkyl group of 1 to 6 carbon atoms
- R 4 and R 5 are each independently a hydrogen atom, a saturated or unsaturated alkyl group of 1 to 20 carbon atoms; a saturated or unsaturated cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms
- R 6 is an ethylenically unsaturated bond and a carbon an organic group having 2 to 12 carbon atoms having at least one carbon triple bond
- R 7 and R 8 are each independently an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a carbon It is an aralkyl group having 7 to 10 atoms, wherein multiple R 5 may be the same or different, multiple R 7 may be the same or different, and multiple R 8 may be the same.
- Each of R 1 to R 8 may be independently partially substituted with a substituent or a halogen atom, y is a positive number, t, u, v, w, x and z are each independently 0 or a positive number, and at least one of u and v is a positive number.
- ⁇ 2> The silsesquioxane derivative according to ⁇ 1>, wherein t, x and z in the formula (1) are 0 and 0.01 ⁇ y/(u+v+w) ⁇ 0.5.
- ⁇ 3> The silsesquioxane derivative according to ⁇ 1> or ⁇ 2>, wherein u and v are each independently a positive number and 0 ⁇ v/u ⁇ 1 in the formula (1).
- ⁇ 4> The silsesquioxane derivative according to any one of ⁇ 1> to ⁇ 3>, which has a viscosity of 10 mPa ⁇ s to 4,000 mPa ⁇ s at 25°C.
- ⁇ 5> A curable composition comprising the silsesquioxane derivative according to any one of ⁇ 1> to ⁇ 4> and a polymerization initiator.
- ⁇ 6> A hard coating agent comprising the curable composition according to ⁇ 5>.
- ⁇ 7> A cured product obtained by curing the curable composition according to ⁇ 5>.
- ⁇ 8> A hard coat obtained by curing the hard coat agent according to ⁇ 6>.
- ⁇ 9> A substrate comprising the hard coat according to ⁇ 8>.
- a silsesquioxane derivative capable of producing a cured product having a low viscosity and excellent hardness, a curable composition containing the silsesquioxane derivative, and a cured product obtained by curing the same, A hard coating agent containing this silsesquioxane derivative, a hard coating obtained by curing the same, and a substrate containing this hard coating can be provided.
- each of R 1 to R 8 in formula (1) may be independently partially substituted with a substituent or a halogen atom.
- R 1 to R 8 each independently represent an alkyl group, an aryl group, an aralkyl group, a vinyl group, an epoxy group, an oxetanyl group, a hydroxyl group, an amino group, an alkylamino group, an arylamino group, an aralkylamino group, and an ammonium group. , a thiol group, an isocyanurate group, a ureido group, an isocyanate group, a carboxy group, an acid anhydride group, or a halogen atom.
- R 1 to R 8 in formula (1) may each independently be unsubstituted, for example, R 1 to R 3 or R 6 to R 8 (preferably R 1 to R 3 and R 6 to R 8 ) may be unsubstituted.
- silsesquioxane derivative The silsesquioxane derivative of the present invention is represented by the following formula (1).
- R 1 and R 2 are each independently an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 10 carbon atoms, an arylene group having 6 to 10 carbon atoms, or a number of carbon atoms.
- R 3 is an alkyl group of 1 to 6 carbon atoms
- R 4 and R 5 are each independently a hydrogen atom, a saturated or unsaturated alkyl group of 1 to 20 carbon atoms; a saturated or unsaturated cycloalkyl group having 3 to 8 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms
- R 6 is an ethylenically unsaturated bond and a carbon an organic group having 2 to 12 carbon atoms having at least one carbon triple bond
- R 7 and R 8 are each independently an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a carbon It is an aralkyl group having 7 to 10 atoms, wherein multiple R 5 may be the same or different, multiple R 7 may be the same or different, and multiple R 8 may be the same.
- Each of R 1 to R 8 may be independently partially substituted with a substituent or a halogen atom, y is a positive number, t, u, v, w, x and z are each independently 0 or a positive number, and at least one of u and v is a positive number.
- structural units (a) to (g) Each structural unit that the silsesquioxane derivative of the present invention may contain is referred to as structural units (a) to (g) as follows.
- the silsesquioxane derivative of the present invention includes at least one of the structural units (b) and (c) among the structural units (a) to (g) described above, and the structural unit (f), At least one of structural unit (a), structural unit (d), structural unit (e), and structural unit (g) is included as necessary.
- the silsesquioxane derivative of the present invention contains at least one of the structural unit (b) and the structural unit (c), and the structural unit (f), so that the cured product has a low viscosity and excellent hardness. manufacturing becomes possible.
- t, u, v, w, x, y and z in formula (1) represent molar ratios of structural units (a) to (g).
- t, u, v, w, x, y and z are the structural units (a) to (g) that may be included in the silsesquioxane derivative represented by the formula (1).
- the molar ratio can be obtained from NMR (nuclear magnetic resonance) analysis values of the silsesquioxane derivative of the present invention. Further, when the reaction rate of each raw material of the silsesquioxane derivative is known, or when the yield is 100%, it can be determined from the charged amount of the raw material.
- the molar ratio of each structural unit of the silsesquioxane derivative is calculated by performing 1 H-NMR analysis on a sample dissolved in deuterated chloroform or the like and, if necessary, further performing 29 Si-NMR analysis. You may The structure of the original silsesquioxane derivative may be estimated from the ratio of the structural units obtained by decomposing the structural units with an alkali or the like. If necessary, known techniques such as mass spectrometry and IR (infrared absorption spectroscopy) analysis may be combined to determine the molar ratio of each structural unit of the silsesquioxane derivative.
- Each of the structural units (b) to (g) in formula (1) may be of only one type, or may be of two or more types.
- the order of arrangement in formula (1) indicates the composition of the structural units, and does not mean the order of arrangement of the silsesquioxane derivatives. Therefore, the condensed form of the structural units in the silsesquioxane derivative of the present invention does not necessarily have to follow the sequence of formula (1). Details of the structural units (a) to (g) will be described below.
- Structural unit (a) is a Q unit having 4 O 1/2 atoms (2 oxygen atoms) per silicon atom.
- the Q unit means a unit having 4 O 1/2 atoms per silicon atom.
- the proportion of the structural unit (a) in the silsesquioxane derivative of the present invention is not particularly limited.
- the molar ratio (t/(t+u+v+w+x+y+z)) of the structural unit (a) to all structural units is 0.1 or less from the viewpoint of the viscosity of the silsesquioxane derivative and the hardness of the cured product. is preferred, 0.05 or less is more preferred, and 0 is even more preferred.
- a molar ratio of 0 means that the corresponding structural unit is not included, and the same applies hereinafter.
- Structural unit (b) is a T unit having 3 O 1/2 per silicon atom (1.5 oxygen atoms) and an acryloyloxy group bonded to the silicon atom via R 1 is.
- the T unit means a unit having 3 O 1/2 atoms per 1 silicon atom.
- R 1 is an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 10 carbon atoms, an arylene group having 6 to 10 carbon atoms, or an aralkylene group having 7 to 12 carbon atoms. is the base.
- R 1 is preferably an alkylene group having 1 to 10 carbon atoms or a cycloalkylene group having 3 to 10 carbon atoms, more preferably an alkylene group having 1 to 10 carbon atoms.
- the alkylene group having 1 to 10 carbon atoms is preferably an alkylene group having 1 to 6 carbon atoms, more preferably an alkylene group having 2 to 4 carbon atoms, and even more preferably a propylene group. .
- the alkylene group having 1 to 10 carbon atoms may be linear or branched.
- the cycloalkylene group having 3 to 10 carbon atoms is preferably a cycloalkylene group having 3 to 6 carbon atoms, more preferably a cycloalkylene group having 4 to 6 carbon atoms.
- the cycloalkylene group having 3 to 10 carbon atoms may have a branch.
- the ratio of the structural unit (b) in the silsesquioxane derivative of the present invention is not particularly limited.
- the molar ratio (u/(t+u+v+w+x+y+z)) of the structural unit (b) to all structural units is, from the viewpoint of ultraviolet (hereinafter also referred to as UV) curability, 0.2 to 0.99. It is preferably 0.3 to 0.9, even more preferably 0.35 to 0.8.
- Structural unit (c) is an acryloyloxy group having 3 O 1/2 atoms (1.5 oxygen atoms) per silicon atom, and having a hydrogen atom substituted with R 3 via R 2 is a T unit attached to a silicon atom.
- R 2 is an alkylene group having 1 to 10 carbon atoms, a cycloalkylene group having 3 to 10 carbon atoms, an arylene group having 6 to 10 carbon atoms, or an aralkylene group having 7 to 12 carbon atoms. is the base. Preferred embodiments of R 2 are the same as R 1 in structural unit (b).
- R 3 is an alkyl group having 1 to 6 carbon atoms.
- the alkyl group having 1 to 6 carbon atoms includes, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group, preferably methyl group or ethyl group, more preferably methyl group.
- the ratio of the structural unit (c) in the silsesquioxane derivative of the invention is not particularly limited.
- the molar ratio (v / (t + u + v + w + x + y + z)) of the structural unit (c) to all structural units is preferably 0 to 0.7 from the viewpoint of hardness and UV curability when cured. It is more preferably 0.05 to 0.6, even more preferably 0.1 to 0.5.
- the molar ratio of structural unit (c) to all structural units may be zero.
- At least one of u and v is a positive number, and from the viewpoint of the hardness of the cured product, u and v are preferably independently positive numbers.
- the total molar ratio ((u + v)/(t + u + v + w + x + y + z)) of the structural unit (b) and the structural unit (c) in all structural units is 0.3 to 0.3 from the viewpoint of viscosity and hardness when cured. It is preferably 99, more preferably 0.5 to 0.98, even more preferably 0.7 to 0.95.
- the molar ratio (v/u+v) of the structural unit (c) to the total of the structural unit (b) and the structural unit (c) is 0 to 0.7 from the viewpoint of viscosity and hardness when cured. is preferred, 0.05 to 0.6 is more preferred, and 0.1 to 0.5 is even more preferred.
- Structural unit (d) is a T unit having 3 O 1/2 (1.5 oxygen atoms) per silicon atom and R 4 bonded to the silicon atom.
- R 4 is a hydrogen atom, a saturated or unsaturated alkyl group having 1 to 20 carbon atoms, a saturated or unsaturated cycloalkyl group having 3 to 8 carbon atoms, or 6 to It is an aryl group of 20 or an aralkyl group of 7 to 20 carbon atoms.
- a saturated or unsaturated alkyl group having 1 to 20 carbon atoms may be linear or branched.
- the saturated or unsaturated alkyl group having 1 to 20 carbon atoms is preferably a saturated or unsaturated alkyl group having 1 to 10 carbon atoms, more preferably a saturated alkyl group having 1 to 10 carbon atoms. more preferred.
- saturated alkyl groups having 1 to 10 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group. From the viewpoint of heat resistance and hardness of the cured product, a methyl group or an ethyl group is preferable, and a methyl group is more preferable.
- Examples of unsaturated alkyl groups having 1 to 10 carbon atoms include vinyl groups, 2-propenyl groups, and ethynyl groups.
- a saturated or unsaturated cycloalkyl group having 3 to 8 carbon atoms may have a branch.
- a saturated or unsaturated cycloalkyl group having 3 to 8 carbon atoms is preferably a saturated or unsaturated cycloalkyl group having 4 to 6 carbon atoms.
- the aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 10 carbon atoms.
- Examples of the aryl group having 6 to 20 carbon atoms include a phenyl group, a group in which one or more hydrogen atoms of the phenyl group are substituted with an alkyl group having 1 to 10 carbon atoms, and a naphthyl group.
- a phenyl group is preferred from the viewpoint of heat resistance and hardness of the cured product.
- the aralkyl group having 7 to 20 carbon atoms is preferably an aralkyl group having 7 to 10 carbon atoms.
- Examples of the aralkyl group having 7 to 20 carbon atoms include groups in which one hydrogen atom of an alkyl group having 1 to 10 carbon atoms is substituted with an aryl group such as a phenyl group. Examples thereof include benzyl group and phenethyl group, and benzyl group is preferable from the viewpoint of heat resistance and hardness of the cured product.
- examples of R 4 include a 3-glycidoxypropyl group and a 2-(3,4-epoxycyclohexyl)ethyl group.
- 3-(3-ethyloxetan-3-yl)methoxypropyl group 3-hydroxypropyl group, 3-aminopropyl group, 3-dimethylaminopropyl group, 3-hydroxypropyl group, 3-aminopropyl hydrochloride , hydrochloride of 3-dimethylaminopropyl group, p-styryl group, N-2-(aminoethyl)-3-aminopropyl group, N-phenyl-3-aminopropyl group, N-(vinylbenzyl)-2- Hydrochloride of aminoethyl-3-aminopropyl group, 3-ureidopropyl group, 3-mercaptopropyl group, 3-isocyanatopropyl group, 3-carboxypropyl group and 3-chloropropyl group.
- the ratio of the structural unit (d) in the silsesquioxane derivative of the present invention is not particularly limited.
- the molar ratio (w / (t + u + v + w + x + y + z)) of the structural unit (d) to the total structural units is preferably 0.1 or less, and 0.05 or less, from the viewpoint of the hardness of the cured product. It is more preferably 0, and more preferably 0.
- Structural unit (e) is a D unit having two O 1/2 per silicon atom (one oxygen atom) and two R 5 bonds to the silicon atom.
- the D unit means a unit having two O 1/2 atoms per one silicon atom.
- R 5 is a hydrogen atom, a saturated or unsaturated alkyl group having 1 to 20 carbon atoms, a saturated or unsaturated cycloalkyl group having 3 to 8 carbon atoms, or 6 to It is an aryl group of 20 or an aralkyl group of 7 to 20 carbon atoms.
- multiple R 5 may be the same or different.
- Preferred embodiments of R 5 are the same as R 4 in structural unit (d).
- the ratio of the structural unit (e) in the silsesquioxane derivative of the present invention is not particularly limited.
- the molar ratio (x/(t + u + v + w + x + y + z)) of the structural unit (e) to the total structural units is preferably 0.1 or less, and 0.05 or less, from the viewpoint of the hardness of the cured product. It is more preferably 0, and more preferably 0.
- Structural unit (f) has one O 1/2 per silicon atom (0.5 oxygen atoms), one R 6 and two R 5 are bonded to the silicon atom M Units.
- the M unit means a unit having one O 1/2 per one silicon atom.
- R 6 is an organic group having 2 to 12 carbon atoms and having at least one of an ethylenically unsaturated bond and a carbon-carbon triple bond.
- Examples of the organic group having 2 to 12 carbon atoms and having an ethylenically unsaturated bond include a vinyl group, an orthostyryl group, a methstyryl group, a parastyryl group, an acryloyloxymethyl group, a methacryloyloxymethyl group, and a 2-acryloyloxyethyl group.
- R 7 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. In the structural unit (f), multiple R 7 may be the same or different.
- alkyl groups having 1 to 10 carbon atoms examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group. From the viewpoint of heat resistance and hardness of the cured product, a methyl group or an ethyl group is preferable, and a methyl group is more preferable.
- aryl group having 6 to 10 carbon atoms examples include a phenyl group, a group in which one or more hydrogen atoms of the phenyl group are substituted with an alkyl group having 1 to 4 carbon atoms, and a naphthyl group.
- a phenyl group is preferred from the viewpoint of heat resistance and hardness of the cured product.
- Examples of the aralkyl group having 7 to 10 carbon atoms include groups in which one hydrogen atom of an alkyl group having 1 to 4 carbon atoms is substituted with an aryl group such as a phenyl group. Examples thereof include benzyl group and phenethyl group, and benzyl group is preferable from the viewpoint of heat resistance and hardness of the cured product.
- the proportion of the structural unit (f) in the silsesquioxane derivative of the present invention is not particularly limited.
- the molar ratio (y/(t + u + v + w + x + y + z)) of the structural unit (f) to all structural units is preferably 0.01 to 0.5 from the viewpoint of viscosity and hardness when cured. It is more preferably 0.02 to 0.4, even more preferably 0.05 to 0.35.
- the molar ratio of the structural unit (b) and the structural unit (c) to the structural unit (f) is the viscosity and the cured product. From the viewpoint of hardness, it is preferably 50:50 to 99:1, more preferably 60:40 to 98:2, even more preferably 65:35 to 95:5.
- Structural unit (g) is an M unit having one O 1/2 (0.5 oxygen atom) per silicon atom and three R 8 bonds to the silicon atom.
- R 8 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. In the structural unit (g), multiple R 8 may be the same or different. Preferred embodiments of R 8 are the same as R 7 in structural unit (f).
- the proportion of the structural unit (g) in the silsesquioxane derivative of the present invention is not particularly limited.
- the molar ratio (z / (t + u + v + w + x + y + z)) of the structural unit (g) to all structural units is preferably 0.1 or less, and 0.05 or less, from the viewpoint of the hardness of the cured product. It is more preferably 0, and more preferably 0.
- the silsesquioxane derivative of the present invention may further contain (R 9 O 1/2 ) as a structural unit not containing Si (hereinafter also referred to as structural unit (h)).
- R 9 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- the alkyl group having 1 to 6 carbon atoms may be either an aliphatic group or an alicyclic group, and may be linear or branched. Specific examples of alkyl groups having 1 to 6 carbon atoms include methyl, ethyl, propyl, butyl, pentyl and hexyl groups.
- Structural unit (h) is an alkoxy group which is a hydrolyzable group contained in the silicon compound described later, or an alkoxy group formed by substituting the hydrolyzable group of the silicon compound with an alcohol contained in the reaction solvent. It may be a hydroxyl group that remains in the molecule without hydrolysis or polycondensation, or a hydroxyl group that remains in the molecule without polycondensation after hydrolysis.
- t, x and z are preferably 0, w is preferably 0 or a positive number, and t, w, x and z are more preferably 0.
- 0.01 ⁇ y/(u + v + w) ⁇ 0.5 is preferable, 0.02 ⁇ y/(u + v + w) ⁇ 0.4 is more preferable, and 0.05 ⁇ y It is more preferable that /(u+v+w) ⁇ 0.35.
- u and v are each independently positive numbers, preferably 0 ⁇ v/u ⁇ 1, more preferably 0.1 ⁇ v/u ⁇ 1, and 0.1 ⁇ v/u ⁇ 1. 2 ⁇ v/u ⁇ 1 is more preferable, and 0.3 ⁇ v/u ⁇ 1 is particularly preferable.
- the weight average molecular weight (hereinafter also referred to as "Mw") of the silsesquioxane derivative of the present invention is not particularly limited, and may be, for example, 300 to 30,000, or 500 to 15,000. may be from 700 to 10,000, or from 1,000 to 5,000.
- Mw in the present invention means a value obtained by converting the molecular weight measured by GPC (gel permeation chromatography) using polystyrene as a standard substance.
- GPC gel permeation chromatography
- the silsesquioxane derivative of the present invention preferably has a viscosity at 25° C. of 10 mPa s to 4,000 mPa s, more preferably 50 mPa s to 2,000 mPa s, and 100 mPa s. More preferably, it is up to 1,600 mPa ⁇ s.
- the viscosity at 25° C. means a value measured using an E-type viscometer (cone and plate type viscometer; for example, Toki Sangyo Co., Ltd. TVE22H-type viscometer).
- the silsesquioxane derivative of the present invention can be produced by known methods.
- a method for producing a silsesquioxane derivative is disclosed in detail as a method for producing polysiloxane in WO 2013/031798 pamphlet and the like.
- the silsesquioxane derivative of the present invention can be produced, for example, by the following method.
- the method for producing a silsesquioxane derivative of the present invention comprises a condensation step of hydrolyzing and polycondensing the silicon compound to give the structural unit of formula (1) by condensation in a suitable reaction solvent.
- silicon compound 4" silicon compound 5 (also referred to as “silicon compound 6” or “silicon compound 7").
- silicon compounds 1 to 3 and, if necessary, other silicon compounds may be hydrolyzed and polycondensed.
- a part of the silicon compounds 1 to 3 and, if necessary, other silicon compounds are hydrolyzed and polycondensed to obtain an intermediate silsesquioxane derivative, and then the obtained intermediate product may be further subjected to hydrolysis and polycondensation reactions with the rest of the silicon compounds 1 to 3 and the like.
- the silicon compound 1, the silicon compound 2 and, if necessary, other silicon compounds are hydrolyzed and polycondensed, and then the obtained intermediate product and the silicon compound 3 are combined. may be further subjected to hydrolysis and polycondensation reactions.
- a silicon compound is hydrolyzed and polycondensed in the presence of a reaction solvent, and then the reaction solvent, by-products, residual monomers, water, etc. in the reaction solution are removed. It is preferable to provide a distillation step for distilling off.
- Examples of the silicon compound 1 include (3-acryloyloxypropyl)trimethoxysilane, (3-acryloyloxypropyl)triethoxysilane, (8-acryloyloxyoctyl)trimethoxysilane, and (3-acryloyloxypropyl)trichlorosilane. is mentioned.
- Examples of the silicon compound 2 include (3-methacryloyloxypropyl)trimethoxysilane, (3-methacryloyloxypropyl)triethoxysilane, (8-methacryloyloxyoctyl)trimethoxysilane, and (3-methacryloyloxypropyl)trichlorosilane. is mentioned.
- Examples of the silicon compound 3 include 1,3-divinyltetramethyldisiloxane, 1,3-bis(p-styryl)tetramethyldisiloxane, 1,3-bis(3 -acryloyloxypropyl)tetramethyldisiloxane, 1,3-bis(3-methacryloyloxypropyl)tetramethyldisiloxane, etc., methoxydimethylvinylsilane, ethoxydimethylvinylsilane, chlorodimethylvinylsilane, dimethylvinylsilanol, (3-acryloyl oxypropyl)dimethylmethoxysilane, (3-methacryloyloxypropyl)dimethylmethoxysilane, p-styryldimethylmethoxysilane, ethynyldimethylmethoxysilane and the like.
- Examples of the silicon compound 4 include tetramethoxysilane, tetraethoxysilane, and the like.
- Silicon compound 5 includes, for example, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, propyltrimethoxysilane, octyltrimethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, benzyltrimethoxysilane, cyclohexyltri methoxysilane, vinyltrimethoxysilane, allyltrimethoxysilane, p-styryltrimethoxysilane, ethynyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-
- Examples of the silicon compound 6 include dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldidiethoxysilane, propylmethyldimethoxysilane, octylmethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldiethoxysilane, benzylmethyldimethoxysilane, cyclohexylmethyldimethoxysilane, vinylmethyldimethoxysilane, allylmethyldimethoxysilane, p-styrylmethyldimethoxysilane, ethynylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, N-2 -(aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-aminopropy
- Examples of the silicon compound 7 include hexamethyldisiloxane, trimethylmethoxysilane, trimethylethoxysilane, trimethylchlorosilane, dimethylphenylmethoxysilane, and the like.
- Alcohol may be used as a reaction solvent in the condensation step.
- Alcohol is a narrowly defined alcohol represented by the general formula R--OH, and is a compound having no functional group other than an alcoholic hydroxyl group.
- Alcohol is not particularly limited, and examples include methanol, ethanol, 1-propanol, 2-propanol, 2-butanol, 2-pentanol, 3-pentanol, 2-methyl-2-butanol, 3-methyl-2- butanol, cyclopentanol, 2-hexanol, 3-hexanol, 2-methyl-2-pentanol, 3-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl-3-pentanol, 2-ethyl-2-butanol, 2,3-dimethyl-2-butanol, cyclohexanol and the like.
- the reaction solvent used in the condensation step may be alcohol alone, or may be a mixed solvent with at least one sub-solvent.
- the co-solvent may be either a polar solvent, a non-polar solvent, or a combination of both.
- Hydrolysis and polycondensation reactions in the condensation step proceed in the presence of water.
- the amount of water used to hydrolyze the hydrolyzable group contained in the silicon compound is preferably 0.5 to 5 times the amount (mol) of the substance of the hydrolyzable group, more preferably 1 to 2 times the molar amount.
- the hydrolysis and polycondensation reaction of the silicon compound may be carried out without a catalyst or with a catalyst.
- inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid and phosphoric acid
- acid catalysts exemplified by organic acids such as formic acid, acetic acid, oxalic acid and p-toluenesulfonic acid, ammonia, tetramethylammonium hydroxide, water
- Base catalysts such as sodium oxide, potassium hydroxide, sodium carbonate and potassium carbonate are preferably used, and acid catalysts are more preferably used.
- the amount of the catalyst used is preferably an amount corresponding to 0.01 mol% to 20 mol%, and preferably 0.1 mol% to 10 mol, relative to the total amount (mol) of silicon atoms contained in the silicon compound. % is more preferable.
- an auxiliary agent can be added to the reaction system.
- distillation can be carried out under normal pressure or reduced pressure, can be carried out at room temperature or under heating, and can also be carried out under cooling.
- the method for producing a silsesquioxane derivative can include a neutralization step for neutralizing the catalyst before the distillation step.
- a step of removing salts generated by neutralization by washing with water or the like can also be provided.
- the silsesquioxane derivative represented by formula (1) is a group obtained by adding an acid or the like to an oxetanyl group or an epoxy group to open the ring, among the side chain functional groups derived from the silicon compound used in the production as a raw material. or may contain a hydroxyalkyl group formed by decomposition of an organic group having a (meth)acryloyl group, or a group obtained by adding an acid or the like to an unsaturated hydrocarbon group or the like.
- You can Specific examples thereof include those in which a part of formula (1) includes a structure represented by formula (A) and/or a structure represented by formula (B) below.
- the original organic group having an oxetanyl group or an epoxy group, the original organic group having a (meth)acryloyl group, or the original unsaturated hydrocarbon group derived from the silicon compound as a raw material As long as it is 50 mol % or less with respect to the amount corresponding to the group, there is no problem in carrying out the present invention, and it is preferably 30 mol % or less, more preferably 10 mol % or less.
- the T unit is exemplified, but the same D unit, M unit, etc. may be used.
- the curable composition of the present invention contains the silsesquioxane derivative of the present invention described above and a polymerization initiator.
- the curable composition of the present invention may be used as a hard coating agent.
- the curable composition of the present invention may contain various components (hereinafter also referred to as "other components") as necessary.
- the polymerization initiator is not particularly limited, and examples thereof include photopolymerization initiators and thermal polymerization initiators.
- Photopolymerization initiators include, for example, radical photopolymerization initiators.
- Thermal polymerization initiators include, for example, thermal radical polymerization initiators. A known compound may be used as the photopolymerization initiator and the thermal polymerization initiator.
- Photoradical polymerization initiators include 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1 -[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane- 1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, diethoxyacetophenone, oligo[2-hydroxy-2-methyl-1-[4-(1 -methylvinyl)phenyl]propanone] and acetophenones such as 2-hydroxy-1- ⁇ 4-[4-(2-hydroxy-2-methyl-propionyl)benzyl]phenyl ⁇ -2-methyl-propan-1-one Compound; benzophenone compounds such as benzophenone, 4-phenylbenz
- the thermal radical polymerization initiator is not particularly limited, and examples include peroxides and azo initiators.
- peroxides examples include hydrogen peroxide; inorganic peroxides such as sodium persulfate, ammonium persulfate and potassium persulfate; 1,1-bis(t-butylperoxy) 2-methylcyclohexane, 1,1-bis( t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)-3,3,5-trimethyl cyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, 2,2-bis(4,4-di-butylperoxycyclohexyl)propane, 1,1-bis(t-butylperoxy)cyclododecane, t-hexylperoxyisopropyl monocarbonate, t-butylperoxymaleic acid, t-butylperoxy-3,5,5-tri
- Azo initiators include 2,2′-azobisisobutyronitrile, 1,1′-azobis(cyclohexane-1-carbonitrile), 2-(carbamoylazo)isobutyronitrile, 2-phenylazo-4 Azo compounds such as -methoxy-2,4-dimethylvaleronitrile, azodi-t-octane, azodi-t-butane, etc., may be used alone, or two or more of them may be used in combination.
- a redox reaction can be achieved by combining with a redox polymerization initiation system using a reducing agent such as iron.
- the content of the polymerization initiator is 0.01 parts by mass to 20 parts by mass with respect to 100 parts by mass of the silsesquioxane derivative represented by formula (1). is preferred, 0.1 to 10 parts by mass is more preferred, and 1 to 5 parts by weight is even more preferred.
- Other components are not particularly limited, and examples include solvents, polymerizable compounds other than the silsesquioxane derivative represented by formula (1), resins, silicones, monomers, fillers, surfactants, antistatic agents ( For example, conductive polymer), leveling agent, photosensitizer, UV absorber, antioxidant, heat resistance improver, stabilizer, lubricant, pigment, dye, plasticizer, suspending agent, adhesion imparting agent, nano Examples include particles, nanofibers, nanosheets, and the like.
- the curable composition of the present invention may contain silane-based reactive diluents such as tetraalkoxysilanes, trialkoxysilanes, dialkoxysilanes, monoalkoxysilanes and disiloxanes.
- silane-based reactive diluents such as tetraalkoxysilanes, trialkoxysilanes, dialkoxysilanes, monoalkoxysilanes and disiloxanes.
- the curable composition of the present invention may or may not contain a solvent.
- the solvent include various organic solvents such as aliphatic hydrocarbon solvents, aromatic hydrocarbon solvents, chlorinated hydrocarbon solvents, alcohol solvents, ether solvents, amide solvents, ketone solvents, ester solvents and cellosolve solvents. be done.
- the curable composition of the present invention may contain a polymerizable compound other than the silsesquioxane derivative represented by formula (1) (hereinafter also referred to as "other polymerizable compound"). You don't have to.
- Other polymerizable compounds are not particularly limited as long as they are capable of undergoing a polymerization reaction in the presence of the silsesquioxane derivative represented by formula (1) and the polymerization initiator.
- Other polymerizable compounds include silsesquioxane derivatives other than the silsesquioxane derivative represented by formula (1), (meth)acrylate compounds, compounds having an ethylenically unsaturated group, epoxy compounds (having an epoxy group oxetanyl group-containing compounds), compounds having an oxetanyl group (oxetanyl group-containing compounds), and compounds having a vinyl ether group (vinyl ether compounds).
- silsesquioxane derivatives other than the silsesquioxane derivatives represented by formula (1) include silsesquioxane derivatives consisting only of T units, silsesquioxane derivatives containing T units and D units, and the like. .
- (Meth) acrylate compounds are not particularly limited, compounds having one (meth) acryloyl group (hereinafter also referred to as “monofunctional (meth) acrylate”), and compounds having two or more (meth) acryloyl groups (hereinafter also referred to as “polyfunctional (meth)acrylate”).
- Examples of monofunctional (meth)acrylates include Alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate; monofunctional (meth)acrylates having an alicyclic group such as cyclohexyl (meth)acrylate, tert-butylcyclohexyl (meth)acrylate, isobornyl (meth)acrylate, and tricyclodecanemethylol (meth)acrylate; Monofunctional (meth)acrylates having aromatic groups of benzyl (meth)acrylate and phenyl (meth)acrylate; (Meth)acrylates of phenol ethylene oxide adducts, (meth) acrylates of phenol propylene oxide adducts, (meth) acrylates of modified nonylphenol ethylene oxide adducts, and (meth) acrylates of non
- polyfunctional (meth)acrylates include Polyethylene glycol di(meth)acrylates such as diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate; Polypropylene glycol di(meth)acrylates such as dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate; 1,4-butanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, ethylene oxide-modified neopentyl glycol di(meth)acrylate, ethylene oxide-modified bisphenol A di(meth)acrylate, propylene oxide-modified bisphenol A di(meth)acrylate, ethylene oxide-modified hydrogenated bisphenol A di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropan
- Urethane (meth)acrylates can also be used as polyfunctional (meth)acrylates.
- urethane (meth)acrylate include a compound obtained by addition reaction of organic polyisocyanate and hydroxyl group-containing (meth)acrylate, and a compound obtained by addition reaction of organic polyisocyanate, polyol and hydroxyl group-containing (meth)acrylate.
- Monofunctional (meth)acrylates, polyfunctional (meth)acrylates, and the like may be used alone, or two or more of them may be used in combination, or different types may be used in combination.
- polyols examples include low-molecular-weight polyols, polyether polyols, polyester polyols and polycarbonate polyols.
- Low molecular weight polyols include ethylene glycol, propylene glycol, neopentyl glycol, cyclohexanedimethylol, 3-methyl-1,5-pentanediol, and the like.
- polyether polyols include polypropylene glycol and polytetramethylene glycol.
- polyester polyols reaction products of these low molecular weight polyols and/or polyether polyols with dibasic acids such as adipic acid, succinic acid, phthalic acid, hexahydrophthalic acid and terephthalic acid, or acid components such as anhydrides thereof is mentioned. These may be used alone, or two or more of them may be used in combination, or different types may be used in combination.
- dibasic acids such as adipic acid, succinic acid, phthalic acid, hexahydrophthalic acid and terephthalic acid, or acid components such as anhydrides thereof.
- Organic polyisocyanates include tolylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, 4,4′-diphenylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and isophorone diisocyanate.
- hydroxyl group-containing (meth)acrylates examples include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate; pentaerythritol tri(meth)acrylate; ) acrylates, di(meth)acrylates of isocyanuric acid 3-mol alkylene oxide adducts, and hydroxyl group-containing polyfunctional (meth)acrylates such as dipentaerythritol penta(meth)acrylates. These may be used alone, or two or more of them may be used in combination, or different types may be used in combination.
- the mixing ratio is not particularly limited, for example, 100 mass of the silsesquioxane derivative represented by the formula (1)
- the mixing ratio of the (meth)acrylate compound to 1 part is preferably 0 to 100 parts by mass, more preferably 0 to 50 parts by mass, even more preferably 0 to 20 parts by mass. From the viewpoint of adhesion to the inorganic substance layer, the mixing ratio of the (meth)acrylate compound is preferably low.
- a compound having one ethylenically unsaturated group in one molecule other than the (meth)acrylate compound may be added to the curable composition.
- the ethylenically unsaturated group is preferably a (meth)acryloyl group, a maleimide group, a (meth)acrylamide group, or a vinyl group.
- Specific examples of the compound having an ethylenically unsaturated group include (meth)acrylic acid, a Michael addition type dimer of acrylic acid, N-(2-hydroxyethyl)citraconimide, N,N-dimethylacrylamide, acryloylmorpho Phosphorus, N-vinylpyrrolidone, N-vinylcaprolactam and the like. These may be used alone or in combination of two or more.
- Examples of epoxy compounds include monofunctional epoxy compounds and polyfunctional epoxy compounds.
- Examples of oxetanyl group-containing compounds include monofunctional oxetane compounds and polyfunctional oxetane compounds.
- Examples of vinyl ether compounds include monofunctional vinyl ether compounds and polyfunctional vinyl ether compounds. As these compounds, for example, compounds described in JP-A-2011-42755 may be used.
- the silicone is not particularly limited, and known silicones can be used. Examples include polydimethylsilicone, polydiphenylsilicone, polymethylphenylsilicone, etc., which have functional groups at their terminals and/or side chains. things are preferred.
- the functional group is not particularly limited, and examples thereof include (meth)acryloyl group, epoxy group, oxetanyl group, vinyl group, hydroxyl group, carboxy group, amino group, thiol group and the like.
- the content of the other polymerizable compounds is 0.01 per 100 parts by mass of the silsesquioxane derivative represented by formula (1). It is preferably from 0.1 to 50 parts by mass, even more preferably from 1 to 25 parts by mass.
- the cured product of the present invention is obtained by curing the aforementioned curable composition of the present invention.
- the cured product of the present invention can be obtained by irradiating the curable composition of the present invention with an active energy ray or by heating the curable composition of the present invention.
- the curable composition of the present invention When curing the curable composition of the present invention, it may be after applying the curable composition to the substrate.
- the curable composition of the present invention may or may not contain a solvent. When a solvent is included, it is preferable to cure after removing the solvent.
- the method of applying the curable composition is not particularly limited.
- coating methods include ordinary coating methods such as casting, spin coating, bar coating, dip coating, spray coating, roll coating, flow coating and gravure coating.
- the thickness to which the curable composition of the present invention is applied is not particularly limited, and is appropriately set according to the purpose.
- the substrate to which the curable composition of the present invention is applied is not particularly limited, and examples thereof include wood, metal, inorganic materials, plastics, paper, fibers and fabrics. Metals include copper, silver, iron, aluminum, silicon, silicon steel and stainless steel.
- inorganic materials include metal oxides such as aluminum oxide, silicon oxide, magnesium oxide, zirconium oxide, zinc oxide, indium tin oxide and gallium oxide; metal nitrides such as aluminum nitride, gallium nitride and silicon nitride; silicon carbide and nitride; Examples include ceramics such as boron, mortar, concrete and glass.
- plastics include acrylic resins such as polymethyl methacrylate, polyester resins such as polyethylene terephthalate, polyvinyl chloride resins, polycarbonate resins, epoxy resins, polyamide resins such as nylon and aramid, polyimide resins, polyamideimide resins, 4-fluoro Fluorine resins such as ethylene chloride resins, polyolefin resins such as crosslinked polyethylene resins, vinylidene chloride resins, acrylonitrile-butadiene-styrene (ABS) resins, polystyrene resins, polyacrylonitrile resins, cycloolefin polymers (COP), cycloolefin copolymers (COC) , acetate resins, polyarylates, cellophane, norbornene resins, acetyl cellulose resins such as triacetyl cellulose (TAC), polychloroprene, polyphenylene sulfide, polysulfone
- fibers include natural fibers, regenerated fibers, semi-synthetic fibers, metal fibers, glass fibers, carbon fibers, ceramic fibers and known chemical fibers.
- the fabric may be woven or non-woven, and may be made, for example, using the fibers described above. These materials may be used alone, or two or more of them may be combined, mixed, or composited for use.
- the shape of the substrate is not particularly limited, and examples thereof include plate-like, sheet-like, film-like, rod-like, spherical, fiber-like, powder-like, lens-like and other regular or irregular shapes.
- the curing method and curing conditions are selected depending on whether the curable composition is active energy ray-curable and/or thermosetting. Further, the curing conditions (in the case of active energy ray curing, for example, the type of light source and the amount of light irradiation, and in the case of thermosetting, heating temperature, heating time, etc.) It is appropriately selected depending on the type and amount of the polymerization initiator to be contained, the type of other polymerizable compound, and the like.
- the curing method may be irradiation with an active energy ray using a known active energy ray irradiation device or the like.
- active energy rays include electron beams, and light such as ultraviolet rays, visible rays, and X-rays. Light is preferred, and ultraviolet rays are more preferred from the viewpoint that inexpensive devices can be used.
- Ultraviolet irradiation devices include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, ultraviolet (UV) electrodeless lamps, chemical lamps, black light lamps, microwave-excited mercury lamps, and light-emitting diodes (LEDs). mentioned.
- the intensity of light irradiation to the film coated with the present composition may be selected according to the purpose, application, etc.
- the light irradiation intensity in the light wavelength range effective for polymerization (light with a wavelength of 220 nm to 460 nm is preferably used, although it varies depending on the type of photopolymerization initiator) is 0.1 mW/cm 2 to 1000 mW/cm 2 .
- the irradiation energy should be set as appropriate according to the type of active energy ray, the compounding composition, and the like.
- the light irradiation time to the coating may also be selected according to the purpose, application, etc., and the integrated light amount represented as the product of the light irradiation intensity and the light irradiation time in the light wavelength region is 10 mJ/cm 2 to 7, It is preferable to set the light irradiation time so as to achieve 000 mJ/cm 2 .
- the integrated amount of light is more preferably 200 mJ/cm 2 to 5,000 mJ/cm 2 and even more preferably 500 mJ/cm 2 to 4,000 mJ/cm 2 . When the integrated amount of light is within the above range, curing of the composition proceeds smoothly, and a uniform cured product can be easily obtained.
- heat curing can be appropriately combined before and/or after photocuring.
- the composition is first cured in the portion exposed to light by irradiating light, and then, A two-stage cure can also be performed in which heat is applied to cure the composition in the areas not exposed to light.
- substrates are not particularly limited, and examples thereof include substrates having complex shapes such as fabric, fibrous, powdery, porous, and uneven shapes, and two or more of these shapes. may be combined.
- Thermosetting method When the present composition is a thermosetting composition, its curing method and curing conditions are not particularly limited.
- the curing temperature is preferably 80°C to 200°C, more preferably 100°C to 180°C, even more preferably 110°C to 150°C.
- the curing temperature may be constant or may be increased. You may combine temperature rise and temperature fall.
- the curing time is appropriately selected according to the type of thermal polymerization initiator and the content of other components, and is preferably 10 minutes to 360 minutes, more preferably 30 minutes to 300 minutes, and even more preferably 60 minutes to 240 minutes.
- the silsesquioxane derivative of the present invention has a low viscosity and can produce a cured product having excellent hardness. Due to the low viscosity, it is excellent in coatability without a solvent, and even when a solvent is used, the amount used can be reduced. Since the silsesquioxane derivative of the present invention has a low viscosity, it can be suitably used for applications requiring low viscosity. For example, it can be applied to adhesive applications, inkjet printing, printing applications such as 3D printing, coating agent applications, nanoprinting applications, and the like.
- the silsesquioxane derivative of the present invention when applied to nanoprinting, has a low viscosity and is therefore excellent in fine transfer properties. Moreover, since the silsesquioxane derivative of the present invention can be used without a solvent, it can be cured as it is after being poured into a mold. The silsesquioxane derivative of the present invention may be used in combination with fillers, other polymerizable compounds and the like. Moreover, since the silsesquioxane derivative of the present invention has a low viscosity, it can be mixed with a large amount of filler. Since the cured product of the present invention is excellent in hardness, it can be applied to hard coats, optical members, and the like.
- a hard coat having excellent hardness can be obtained by curing the hard coat agent comprising the curable composition of the present invention.
- the hard coating agent of the present invention may be provided on a substrate, and for example, a substrate provided with a hard coat can be obtained by curing the hard coating agent applied on the substrate.
- the weight average molecular weight (Mw) of the silsesquioxane derivative in each example and each comparative example was measured as follows. Specifically, by gel permeation chromatography (manufactured by Tosoh Corporation, HLC-8320GPC, hereinafter abbreviated as "GPC"), in a tetrahydrofuran solvent at 40 ° C., a GPC column "TSK gel SuperMultiporeHZ-M" (manufactured by Tosoh Corporation ), and the molecular weight in terms of standard polystyrene was calculated from the retention time.
- GPC gel permeation chromatography
- the reaction solution was stirred while the aqueous solution prepared as the mixed solution was added dropwise from the dropping funnel over about 1 hour, and then allowed to stand overnight at room temperature. After that, the solvent and the like in the reaction solution were distilled off under reduced pressure while heating the reaction solution to 60° C. to obtain 145.2 g of a colorless transparent liquid silsesquioxane derivative 1 (S1).
- S1 colorless transparent liquid silsesquioxane derivative 1
- Example 2 to 8 Silsesquioxane derivatives 2 to 8 (S2 to S8 ).
- S2 to S8 3-acryloxypropyltrimethoxysilane (corresponding to structural unit (b)) and 3-methacryloxypropyltrimethoxysilane ( (corresponding to structural unit (c)) was used.
- Table 1 shows the molar ratio of each structural unit in the silsesquioxane derivatives, the viscosity at 25° C. and the weight average molecular weight (Mw).
- photocurable compositions 1 to 13 were prepared as follows. Using the prepared photocurable compositions 1 to 13, evaluation of UV curability and pencil hardness test were carried out. Details are described below.
- Photocurable compositions 1 to 13 (Preparation of photocurable composition) 0.03 part by mass of 2-hydroxy-2-methyl-1-phenylpropan-1-one is added to 1 part by mass of the synthesized silsesquioxane derivative 1 to 13, and the mixture is stirred with a rotation/revolution mixer. Photocurable compositions 1 to 13 (P1 to P13) were prepared by doing so. In the photocurable compositions 1 to 13, since the solvent and the like are removed by distillation during the synthesis of the silsesquioxane derivatives 1 to 13, the photocurable compositions 1 to 13 substantially contain a solvent. not
- a high-pressure mercury lamp was used as a UV light source, and each photocurable composition was irradiated with only a short wavelength of 365 nm through a heat ray cut filter, a bandpass filter, and a light reduction filter.
- the UV irradiation intensity at this time was 10 mW/cm 2 .
- UV curability was evaluated according to the following criteria based on the value of storage elastic modulus of each photocurable composition when UV was irradiated for 10 seconds. Excellent UV curability in the order of A>B>C. Table 1 shows the experimental results.
- B 1.0 ⁇ 10 6 Pa or more and less than 5.0 ⁇ 10 6 Pa C: Less than 1.0 ⁇ 10 6 Pa
- Lamp High pressure mercury lamp Height: 10cm Conveyor speed: 5.75m/min Accumulated amount of light per pass: 360 mJ/cm 2 (UV-A) Atmosphere: Atmosphere Number of passes: 10 times
- the photocured film prepared as described above was subjected to a pencil hardness test according to JIS K5600-5-4.
- a pencil hardness test was conducted using a 3H pencil when the PET film was used as the substrate, and an 8H pencil when the SPCC steel plate was used as the substrate.
- the scratch test was performed 10 times for each photocured film, and the number of times the photocured film had no defect was shown in %. The higher the % value, the higher the hardness of the photocured film. Table 1 shows the experimental results.
- the silsesquioxane derivatives obtained in Examples 1-8 had lower viscosities at 25° C. than Comparative Examples 1-3. Furthermore, the silsesquioxane derivatives obtained in Examples 1 to 8 had the same viscosity at 25° C. as compared with Comparative Example 4, and a photocured film having excellent hardness could be produced. . In addition, the silsesquioxane derivatives obtained in Examples 1 to 8 had a lower viscosity at 25° C. than Comparative Example 5, and a photocured film excellent in hardness could be produced.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Silicon Polymers (AREA)
Abstract
Description
[特許文献2]特開2013-035918号公報
[特許文献3]国際公開2020/203472号パンフレット
<1> 下記式(1)で表されるシルセスキオキサン誘導体。
<2> 前記式(1)中、t、x及びzは0であり、0.01≦y/(u+v+w)≦0.5である、<1>に記載のシルセスキオキサン誘導体。
<3> 前記式(1)中、u及びvはそれぞれ独立に正の数であり、0<v/u≦1である、<1>又は<2>に記載のシルセスキオキサン誘導体。
<4> 25℃における粘度は、10mPa・s~4,000mPa・sである、<1>~<3>のいずれか1つに記載のシルセスキオキサン誘導体。
<6> <5>に記載の硬化性組成物からなる、ハードコート剤。
<7> <5>に記載の硬化性組成物を硬化させてなる、硬化物。
<8> <6>に記載のハードコート剤を硬化させてなる、ハードコート。
<9> <8>に記載のハードコートを備える基材。
本明細書において「~」を用いて示された数値範囲には、「~」の前後に記載される数値がそれぞれ最小値及び最大値として含まれる。
本明細書中に段階的に記載されている数値範囲において、一つの数値範囲で記載された上限値又は下限値は、他の段階的な記載の数値範囲の上限値又は下限値に置き換えてもよい。また、本明細書中に記載されている数値範囲において、その数値範囲の上限値又は下限値は、実施例に示されている値に置き換えてもよい。
また、本明細書において、2以上の好ましい態様の組み合わせは、より好ましい態様である。
式(1)中のR1~R8は、それぞれ独立に無置換であってもよく、例えば、R1~R3又はR6~R8(好ましくは、R1~R3及びR6~R8)は、無置換であってもよい。
本発明のシルセスキオキサン誘導体は、下記式(1)で表される。
例えば、シルセスキオキサン誘導体の各構成単位のモル比については、重クロロホルム等に溶解した試料に対して1H-NMR分析を行い、必要に応じてさらに29Si-NMR分析も行うことにより算出してもよい。
アルカリ等で構成単位に分解して構成単位の比率等から元々のシルセスキオキサン誘導体の構造を推定してもよい。
必要に応じて質量分析、IR(赤外吸収分光)分析等の公知の手法を組み合わせてシルセスキオキサン誘導体の各構成単位のモル比を求めてもよい。
以下、構成単位(a)~(g)の詳細について説明する。
構成単位(a)は、ケイ素原子1個に対してO1/2を4個(酸素原子として2個)備えるQ単位である。なお、Q単位とは、ケイ素原子1個に対してO1/2を4個有する単位を意味する。
構成単位(b)は、ケイ素原子1個に対してO1/2を3個(酸素原子として1.5個)備え、R1を介してアクリロイルオキシ基がケイ素原子に結合しているT単位である。なお、T単位とは、ケイ素原子1個に対してO1/2を3個有する単位を意味する。
炭素原子数3~10のシクロアルキレン基は、炭素原子数3~6のシクロアルキレン基であることが好ましく、炭素原子数4~6のシクロアルキレン基であることがより好ましい。炭素原子数3~10のシクロアルキレン基は、分岐を有していてもよい。
構成単位(c)は、ケイ素原子1個に対してO1/2を3個(酸素原子として1.5個)備え、R2を介して、水素原子がR3に置換されたアクリロイルオキシ基がケイ素原子に結合しているT単位である。
全構成単位に占める構成単位(c)のモル比は、0であってもよい。
構成単位(d)は、ケイ素原子1個に対してO1/2を3個(酸素原子として1.5個)備え、R4がケイ素原子に結合しているT単位である。
構成単位(e)は、ケイ素原子1個に対してO1/2を2個(酸素原子として1個)備え、2つのR5がケイ素原子に結合しているD単位である。なお、D単位とは、ケイ素原子1個に対してO1/2を2個有する単位を意味する。
構成単位(f)は、ケイ素原子1個に対してO1/2を1個(酸素原子として0.5個)備え、1つのR6及び2つのR5がケイ素原子に結合しているM単位である。なお、M単位とは、ケイ素原子1個に対してO1/2を1個有する単位を意味する。
構成単位(g)は、ケイ素原子1個に対してO1/2を1個(酸素原子として0.5個)備え、3つのR8がケイ素原子に結合しているM単位である。
本発明のシルセスキオキサン誘導体は、さらにSiを含まない構成単位として(R9O1/2)を含んでいてもよい(以下、構成単位(h)とも称する)。
ここで、R9は水素原子又は炭素原子数1~6のアルキル基である。炭素原子数1~6のアルキル基は、脂肪族基及び脂環族基のいずれでもよく、又、直鎖状及び分岐状のいずれでもよい。炭素原子数1~6のアルキル基の具体例としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、及びヘキシル基が挙げられる。
本発明のシルセスキオキサン誘導体の重量平均分子量(以下、「Mw」とも称する。)は、特に限定されず、例えば、300~30,000であってもよく、500~15,000であってもよく、700~10,000であってもよく、1,000~5,000であってもよい。
なお、本発明におけるMwは、GPC(ゲル浸透クロマトグラフィー)により測定した分子量を、標準物質としてポリスチレンを使用して換算した値を意味する。Mwの測定条件としては、例えば、後述の〔実施例〕における測定条件を用いることができる。
本発明のシルセスキオキサン誘導体では、25℃における粘度は、10mPa・s~4,000mPa・sであることが好ましく、50mPa・s~2,000mPa・sであることがより好ましく、100mPa・s~1,600mPa・sであることがさらに好ましい。
なお、本発明において25℃における粘度とは、E型粘度計(コーンプレート型粘度計。例えば、東機産業(株)TVE22H形粘度計)を使用して測定した値を意味する。
本発明のシルセスキオキサン誘導体は、公知の方法で製造することができる。シルセスキオキサン誘導体の製造方法は、国際公開2013/031798号パンフレット等においてポリシロキサンの製造方法として詳細に開示されている。
本発明のシルセスキオキサン誘導体の製造方法は、適当な反応溶媒中で、縮合により、上記式(1)中の構成単位を与えるケイ素化合物の加水分解及び重縮合反応を行う縮合工程を備える。この縮合工程においては、例えば、構成単位(b)(T単位)を形成するシロキサン結合生成基を3個有するケイ素化合物(以下、「ケイ素化合物1」とも称する。)及び構成単位(c)(T単位)を形成するシロキサン結合生成基を3個有するケイ素化合物(以下、「ケイ素化合物2」とも称する。)の少なくとも一方と、シロキサン結合生成基を1個有する構成単位(f)(M単位)を形成するケイ素化合物(以下、「ケイ素化合物3」とも称する。)と、を少なくとも用いる。また、必要に応じて、構成単位(a)、構成単位(d)、構成単位(e)又は構成単位(g)を形成するその他のケイ素化合物(以下、それぞれ「ケイ素化合物4」「ケイ素化合物5」「ケイ素化合物6」又は「ケイ素化合物7」とも称する。)を使用してもよい。
アルコールとしては特に限定されず、例えば、メタノール、エタノール、1-プロパノール、2-プロパノール、2-ブタノール、2-ペンタノール、3-ペンタノール、2-メチル-2-ブタノール、3-メチル-2-ブタノール、シクロペンタノール、2-ヘキサノール、3-ヘキサノール、2-メチル-2-ペンタノール、3-メチル-2-ペンタノール、2-メチル-3-ペンタノール、3-メチル-3-ペンタノール、2-エチル-2-ブタノール、2,3-ジメチル-2-ブタノール及びシクロヘキサノール等が挙げられる。これらの中でも、2-プロパノール、2-ブタノール、2-ペンタノール、3-ペンタノール、3-メチル-2-ブタノール、シクロペンタノール、2-ヘキサノール、3-ヘキサノール、3-メチル-2-ペンタノール、シクロヘキサノール等の第2級アルコールが好ましい。
縮合工程においては、これらのアルコールを1種又は2種以上組み合わせて用いてもよい。
ケイ素化合物に含まれる加水分解性基を加水分解させるために用いられる水の量は、加水分解性基の物質量(モル)に対して好ましくは0.5~5倍モル、より好ましくは1~2倍モルである。
又、ケイ素化合物の加水分解及び重縮合反応は、無触媒で行ってもよいし、触媒を使用して行ってもよい。触媒を用いる場合は、硫酸、硝酸、塩酸及びリン酸等の無機酸;ギ酸、酢酸、シュウ酸及びパラトルエンスルホン酸等の有機酸に例示される酸触媒、アンモニア、水酸化テトラメチルアンモニウム、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム及び炭酸カリウム等の塩基触媒などが好ましく用いられ、酸触媒がより好ましく用いられる。
触媒の使用量は、ケイ素化合物に含まれるケイ素原子の合計量(モル)に対して、0.01モル%~20モル%に相当する量であることが好ましく、0.1モル%~10モル%に相当する量であることがより好ましい。
本発明の硬化性組成物は、前述の本発明のシルセスキオキサン誘導体と重合開始剤とを含む。本発明の硬化性組成物は、ハードコート剤としてもよい。
本発明の硬化性組成物は、必要に応じて種々の成分(以下、「その他の成分」とも称する)を含んでいてもよい。
重合開始剤としては、特に限定されず、例えば、光重合開始剤及び熱重合開始剤が挙げられる。光重合開始剤としては、例えば、光ラジカル重合開始剤が挙げられる。
熱重合開始剤としては、例えば、熱ラジカル重合開始剤が挙げられる。
光重合開始剤及び熱重合開始剤としては、公知の化合物を用いてもよい。
これらは1種のみ用いてもよく、2種以上を併用することもできる。
又、過酸化物と、アスコルビン酸、アスコルビン酸ナトリウム、エリソルビン酸ナトリウム、酒石酸、クエン酸、ホルムアルデヒドスルホキシラートの金属塩、チオ硫酸ナトリウム、亜硫酸ナトリウム、重亜硫酸ナトリウム、メタ重亜硫酸ナトリウム、塩化第二鉄等の還元剤とを併用したレドックス重合開始系と組み合わせることによりレドックス反応とすることも可能である。
その他の成分としては、特に限定されず、例えば、溶媒、式(1)で表されるシルセスキオキサン誘導体以外の重合性化合物、樹脂、シリコーン、モノマー、フィラー、界面活性剤、帯電防止剤(例えば導電性ポリマー)、レベリング剤、光増感剤、紫外線吸収剤、酸化防止剤、耐熱性向上剤、安定剤、潤滑剤、顔料、染料、可塑剤、懸濁剤、密着性付与剤、ナノ粒子、ナノファイバー、ナノシート等が挙げられる。本発明の硬化性組成物は、テトラアルコキシシラン類、トリアルコキシシラン類、ジアルコキシシラン類、モノアルコキシシラン類及びジシロキサン類等のシラン系反応性希釈剤等を含んでいてもよい。
溶媒としては、例えば、脂肪族系炭化水素溶媒、芳香族系炭化水素溶媒、塩素化炭化水素溶媒、アルコール溶媒、エーテル溶媒、アミド溶媒、ケトン溶媒、エステル溶媒及びセロソルブ溶媒等の各種有機溶媒が挙げられる。
その他の重合性化合物としては、式(1)で表されるシルセスキオキサン誘導体及び重合開始剤の存在下にて重合反応可能な化合物であれば特に限定されない。その他の重合性化合物としては、式(1)で表されるシルセスキオキサン誘導体以外のシルセスキオキサン誘導体、(メタ)アクリレート化合物、エチレン性不飽和基を有する化合物、エポキシ化合物(エポキシ基を有する化合物)、オキセタニル基を有する化合物(オキセタニル基含有化合物)、ビニルエーテル基を有する化合物(ビニルエーテル化合物)等が挙げられる。
メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、及び2-エチルヘキシル(メタ)アクリレート等のアルキル(メタ)アクリレート;
シクロヘキシル(メタ)アクリレート、tert-ブチルシクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、及びトリシクロデカンメチロール(メタ)アクリレート等の脂環式基を有する単官能(メタ)アクリレート;
ベンジル(メタ)アクリレート、及びフェニル(メタ)アクリレートの芳香族基を有する単官能(メタ)アクリレート;
フェノールエチレンオキサイド付加物の(メタ)アクリレート、フェノールプロピレンオキサイド付加物の(メタ)アクリレート、変性ノニルフェノールエチレンオキサイド付加物の(メタ)アクリレート、及びノニルフェノールプロピレンオキサイド付加物の(メタ)アクリレート、パラクミルフェノールのアルキレンオキサイド付加物の(メタ)アクリレート、オルトフェニルフェノール(メタ)アクリレート、及びオルトフェニルフェノールのアルキレンオキサイド付加物の(メタ)アクリレート等のフェノール誘導体のアルキレンオキサイド付加物の(メタ)アクリレート;
2-エチルヘキシルカルビトール(メタ)アクリレート等のアルコキシアルキル基を有する単官能(メタ)アクリレート;
テトラヒドロフルフリル(メタ)アクリレート、及びN-(2-(メタ)アクリロキシエチル)ヘキサヒドロフタルイミド等の複素環を有する単官能(メタ)アクリレート;
ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヒドロキシブチル(メタ)アクリレート、及びヒドロキシヘキシル(メタ)アクリレート等のヒドロキシルアルキル(メタ)アクリレート;
2-ヒドロキシ-3-フェノキシプロピル(メタ)アクリレート等のヒドロキシル基及び芳香族基を有する単官能(メタ)アクリレート;
ジエチレングリコールモノ(メタ)アクリレート、ジプロピレングリコールモノ(メタ)アクリレート、トリエチレングリコールモノ(メタ)アクリレート、トリプロピレングリコールモノ(メタ)アクリレート等のアルキレングルコールモノ(メタ)アクリレート;並びに
ω-カルボキシポリカプロラクトンモノ(メタ)アクリレート、及びフタル酸モノヒドロキシエチル(メタ)アクリレート等のカルボキシ基を有する単官能(メタ)アクリレート等が挙げられる。
ジエチレングリコールジ(メタ)アクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート等のポリエチレングリコールジ(メタ)アクリレート;
ジプロピレングリコールジ(メタ)アクリレート、トリプロピレングリコールジ(メタ)アクリレート、テトラプロピレングリコールジ(メタ)アクリレート等のポリプロピレングリコールジ(メタ)アクリレート;
1,4-ブタンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、エチレンオキサイド変性ネオペンチルグリコールのジ(メタ)アクリレート、エチレンオキサイド変性ビスフェノールAのジ(メタ)アクリレート、プロピレンオキサイド変性ビスフェノールAのジ(メタ)アクリレート、エチレンオキサイド変性水添ビスフェノールAのジ(メタ)アクリレート、トリメチロールプロパンジ(メタ)アクリレート、トリメチロールプロパンアリルエーテルジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、エチレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレート、プロピレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート及びジペンタエリスリトールヘキサアクリレート等が挙げられる。
ウレタン(メタ)アクリレートとしては、有機ポリイソシアネートとヒドロキシル基含有(メタ)アクリレートを付加反応させた化合物、有機ポリイソシアネートとポリオールとヒドロキシル基含有(メタ)アクリレートとを付加反応させた化合物等が挙げられる。
単官能(メタ)アクリレート、多官能(メタ)アクリレート等は、1種のみ用いてもよく、2種以上を併用することもでき、異なる種類のものを併用することもできる。
低分子量ポリオールとしては、エチレングリコール、プロピレングリコール、ネオペンチルグリコール、シクロヘキサンジメチロール、及び3-メチル-1,5-ペンタンジオール等が挙げられる。
ポリエーテルポリオールとしては、ポリプロピレングリコール、ポリテトラメチレングリコール等が挙げられる。
ポリエステルポリオールとしては、これら低分子量ポリオール及び/又はポリエーテルポリオールと、アジピン酸、コハク酸、フタル酸、ヘキサヒドロフタル酸及びテレフタル酸等の二塩基酸又はその無水物等の酸成分との反応物が挙げられる。
これらは1種のみ用いてもよく、2種以上を併用することもでき、異なる種類のものを併用することもできる。
ヒドロキシル基含有(メタ)アクリレートとしては、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、4-ヒドロキシブチル(メタ)アクリレート等のヒドロキシアルキル(メタ)アクリレート;ペンタエリスリトールトリ(メタ)アクリレート、イソシアヌル酸のアルキレンオキサイド3モル付加物のジ(メタ)アクリレート及びジペンタエリスリトールペンタ(メタ)アクリレート等のヒドロキシル基含有多官能(メタ)アクリレート等が挙げられる。
これらは1種のみ用いてもよく、2種以上を併用することもでき、異なる種類のものを併用することもできる。
前記エチレン性不飽和基としては、(メタ)アクリロイル基、マレイミド基、(メタ)アクリルアミド基、又はビニル基が好ましい。
前記エチレン性不飽和基を有する化合物の具体例としては、(メタ)アクリル酸、アクリル酸のマイケル付加型のダイマー、N-(2-ヒドロキシエチル)シトラコンイミド、N,N-ジメチルアクリルアミド、アクリロイルモルフォリン、N-ビニルピロリドン及びN-ビニルカプロラクタム等が挙げられる。
これらは1種のみ用いてもよく、2種以上を併用することもできる。
オキセタニル基含有化合物としては、単官能オキセタン化合物、多官能オキセタン化合物等が挙げられる。
ビニルエーテル化合物としては、単官能ビニルエーテル化合物、多官能ビニルエーテル化合物等が挙げられる。
これらの化合物として、例えば、特開2011-42755号公報に記載の化合物を用いてもよい。
シリコーンとしては、特に制限はなく、公知のものが使用でき、例えば、ポリジメチルシリコーン、ポリジフェニルシリコーン、ポリメチルフェニルシリコーン等が挙げられ、その末端及び/又は側鎖に官能基を有しているものが好ましい。前記官能基としては、特に制限はなく、例えば、(メタ)アクリロイル基、エポキシ基、オキセタニル基、ビニル基、水酸基、カルボキシ基、アミノ基、チオール基等が挙げられる。
本発明の硬化物は、前述の本発明の硬化性組成物を硬化させてなる。例えば、本発明の硬化性組成物に活性エネルギー線を照射する、あるいは本発明の硬化性組成物を加熱することで、本発明の硬化物が得られる。
本発明の硬化性組成物は溶媒を含んでも、含まなくてもよい。溶媒を含む場合には、溶媒を除去してから硬化させることが好ましい。
本発明の硬化性組成物を塗布する厚さに特に制限はなく、目的に応じて適切に設定される。
本発明の硬化性組成物が塗布される基材としては、特に制限はなく、木材、金属、無機材料、プラスチック、紙、繊維及び布帛等が挙げられる。
金属としては、銅、銀、鉄、アルミニウム、シリコン、ケイ素鋼及びステンレス等が挙げられる。無機材料としては、酸化アルミニウム、酸化ケイ素、酸化マグネシウム、酸化ジルコニウム、酸化亜鉛、酸化インジウムスズ、酸化ガリウム等の金属酸化物、窒化アルミニウム、窒化ガリウム、窒化ケイ素等の金属窒化物、炭化ケイ素及び窒化ホウ素等のセラミックス、モルタル、コンクリート及びガラス等が挙げられる。
プラスチックの具体例としては、ポリメチルメタクリレート等のアクリル樹脂、ポリエチレンテレフタレート等のポリエステル樹脂、ポリ塩化ビニル樹脂、ポリカーボネート樹脂、エポキシ樹脂、ナイロン、アラミド等のポリアミド樹脂、ポリイミド樹脂、ポリアミドイミド樹脂、4フッ化エチレン樹脂等のフッ素樹脂、架橋ポリエチレン樹脂等のポリオレフィン樹脂、塩化ビニリデン樹脂、アクリロニトリル-ブタジエン-スチレン(ABS)樹脂、ポリスチレン樹脂、ポリアクリロニトリル樹脂、シクロオレフィンポリマー(COP)、シクロオレフィンコポリマー(COC)、アセテート系樹脂、ポリアリレート、セロファン、ノルボルネン系樹脂、トリアセチルセルロース(TAC)等のアセチルセルロース樹脂、ポリクロロプレン、ポリフェニレンスルフィド、ポリスルホン、ポリエーテルスルホン、ポリエーテルエーテルケトン、ポリウレタン樹脂及びガラスエポキシ樹脂等の複合樹脂、各種の繊維強強化樹脂等が挙げられる。
繊維としては、天然繊維、再生繊維、半合成繊維、金属繊維、ガラス繊維、カーボン繊維、セラミック繊維及び公知の化学繊維等が挙げられる。布帛は織布であっても不織布であってもよく、例えば前述の繊維を用いて作製することができる。
これらの材料は単独で用いてもよく、2種以上を組み合わせたり、混合したり、複合化して用いても良い。
基材の形状に特に制限はなく、例えば、板状、シート状、フィルム状、棒状、球状、繊維状、粉末状、レンズ状及びその他の規則的又は不規則的な形状等が挙げられる。
本発明において、硬化性組成物が、活性エネルギー線硬化性であるか、及び/又は熱硬化性であるかにより、その硬化方法及び硬化条件が選択される。又、硬化条件(活性エネルギー線硬化性の場合は、例えば、光源の種類及び光照射量等であり、熱硬化性の場合は、加熱温度及び加熱時間等である。)は、本組成物に含有される重合開始剤の種類、量及び他の重合性化合物の種類等によって、適宜、選択される。
本組成物が、活性エネルギー線硬化性組成物である場合、その硬化方法としては、公知の活性エネルギー線照射装置等によって活性エネルギー線照射を行えばよい。活性エネルギー線としては、電子線、及び、紫外線、可視光線並びにX線等の光等が挙げられ、光が好ましく、安価な装置を使用できる観点から、紫外線がより好ましい。
紫外線照射装置としては、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、メタルハライドランプ、紫外線(UV)無電極ランプ、ケミカルランプ、ブラックライトランプ、マイクロウェーブ励起水銀灯及び発光ダイオード(LED)等が挙げられる。
本組成物を塗布した被膜への光照射強度は、目的、用途等に応じて選択すればよく、活性エネルギー線重合開始剤(光硬化性の場合は、光重合開始剤と称する。)の活性化に有効な光波長領域(光重合開始剤の種類によって異なるが、好ましくは220nm~460nmの波長の光が用いられる。)における光照射強度は、0.1mW/cm2~1000mW/cm2であることが好ましい。
又、照射エネルギーは、活性エネルギー線の種類、配合組成等に応じて適宜設定すべきものである。前記被膜への光照射時間も、目的、用途等に応じて選択すればよく、前記光波長領域における光照射強度及び光照射時間の積として表される積算光量が、10mJ/cm2~7,000mJ/cm2となるように光照射時間が設定されることが好ましい。積算光量は、200mJ/cm2~5,000mJ/cm2がより好ましく、500mJ/cm2~4,000mJ/cm2がさらに好ましい。積算光量が前記範囲にあれば、組成物の硬化が円滑に進行し、均一な硬化物を容易に得ることができる。
例えば、光を照射した際に、陰となる部位を持つ基材に、本組成物を染み込ませる等した後に、光を照射して、光が当たる部位の本組成物をまず硬化し、その後、熱を加えて光の当たらない部位の本組成物を硬化させる、二段階硬化を行うこともできる。このような基材に特に制限はなく、例えば、布帛状、繊維状、粉末状、多孔質状及び凹凸状等の複雑な形状である基材が挙げられ、これらの形状のうちの2つ以上が組み合わせられた形状であってもよい。
本組成物が、熱硬化性組成物である場合、その硬化方法及び硬化条件は、特に限定されない。
硬化温度は、80℃~200℃が好ましく、100℃~180℃がより好ましく、110℃~150℃がさらに好ましい。硬化温度は、温度を一定としてもよいし、昇温させてもよい。昇温と降温とを組み合わせてもよい。
硬化時間は、熱重合開始剤の種類及び他の成分の含有割合等により適宜選択され、10分~360分が好ましく、30分~300分がより好ましく、60分~240分がさらに好ましい。前記の好ましい条件で組成物を硬化させることにより、膨れ、クラック等のない均一な硬化膜を形成することができる。
本発明のシルセスキオキサン誘導体は、低粘度であり、かつ、硬度に優れる硬化物を製造可能である。低粘度であることにより、無溶媒での塗布性に優れ、また溶媒を使用する場合であってもその使用量を削減することができる。
本発明のシルセスキオキサン誘導体は、低粘度であるため、低粘度が要求される用途に好適に使用可能である。例えば、接着剤用途、インクジェット、3Dプリント等の印刷用途、コーティング剤用途、ナノプリント用途等に適用可能である。また、ナノプリント用途に適用した場合に、本発明のシルセスキオキサン誘導体は低粘度であるため、微細転写性に優れる。また、本発明のシルセスキオキサン誘導体は無溶媒で使用可能なため、型に流し込んだ後、そのまま硬化させることが可能となる。
本発明のシルセスキオキサン誘導体をフィラー、他の重合性化合物等と併用して使用してもよい。また、本発明のシルセスキオキサン誘導体は低粘度であるため、多量のフィラーと混合することも可能である。
本発明の硬化物は、硬度に優れるため、ハードコート、光学部材等に適用することができる。また、本発明の硬化性組成物からなるハードコート剤を硬化することで硬度に優れるハードコートが得られる。本発明のハードコート剤は、基材上に設けられていてもよく、例えば、基材上に塗布されたハードコート剤を硬化することでハードコートを備える基材が得られる。
各実施例及び各比較例におけるシルセスキオキサン誘導体の重量平均分子量(Mw)は以下のようにして測定した。具体的には、ゲルパーミエーションクロマトグラフ(東ソー社製、HLC-8320GPC、以下、「GPC」と略す)により、テトラヒドロフラン溶媒中、40℃において、GPCカラム「TSK gel SuperMultiporeHZ-M」(東ソー社製)を用いて分離し、リテンションタイムから標準ポリスチレン換算の分子量を算出した。
各実施例及び各比較例におけるシルセスキオキサン誘導体について、東機産業(株)製TVE22H形粘度計を用い、25℃における粘度を測定した。
各実施例及び各比較例におけるシルセスキオキサン誘導体の各構成単位のモル比については、重クロロホルムに溶解した試料に対して1H-NMR分析を行い、必要に応じてさ
らに29Si-NMR分析も行うことにより算出した。
(シルセスキオキサン誘導体の合成)
温度計、滴下ロート及び攪拌翼を取り付けた1Lの4つ口丸底フラスコに、(3-アクリロイルオキシ)プロピルトリメトキシシラン(167.8g、0.716mol、構成単位(b)に対応)、1,3-ジビニルテトラメチルジシロキサン(26.5g、0.142mol、構成単位(f)に対応)、2-プロパノール(166.3g)及び4-メトキシフェノール(0.025g)を量り取り、水浴中約30℃でよく攪拌した。別途35%塩酸(1.0g、塩化水素として9.6mmol)及び純水(40.6g)を混合して水溶液を調製した。混合液に調製した水溶液を、滴下ロートから約1時間かけて滴下しながら反応液を攪拌した後、室温で一晩静置した。その後、反応液を60℃まで加熱しながら反応液中の溶媒等を減圧留去し、無色透明液体のシルセスキオキサン誘導体1(S1)145.2gを得た。S1に対する1H-NMR分析により、各構成単位は原料の仕込み比通りに定量的に導入されていることを確認した。合成されたシルセスキオキサン誘導体1について、25℃における粘度は400mPa・sであり、重量平均分子量(Mw)は1250であった。
原材料の仕込み量を実施例1に替えて表1のように変更し、溶媒等の量を適宜変更したこと以外は、実施例1と同様にしてシルセスキオキサン誘導体2~8(S2~S8)を得た。なお、実施例6~8では、シルセスキオキサン誘導体のT単位を構成する原料として、3-アクリロキシプロピルトリメトキシシラン(構成単位(b)に対応)とともに3-メタクリロキシプロピルトリメトキシシラン(構成単位(c)に対応)を使用した。
合成されたシルセスキオキサン誘導体2~8について、シルセスキオキサン誘導体における各構成単位のモル比、25℃における粘度及び重量平均分子量(Mw)を表1に示す。
原材料の仕込み量を実施例1に替えて表1のように変更し、溶媒等の量を適宜変更したこと以外は、実施例1と同様にしてシルセスキオキサン誘導体9~13(S9~S13)を得た。なお、比較例4では、シルセスキオキサン誘導体のM単位を構成する原料として、1,3-ジビニルテトラメチルジシロキサンに替えてヘキサメチルジシロキサン(構成単位(g)に対応)を使用し、比較例5では、シルセスキオキサン誘導体のD単位を構成する原料として、ジメトキシジメチルシラン(構成単位(e)に対応)を使用した。
合成されたシルセスキオキサン誘導体9~13について、シルセスキオキサン誘導体における各構成単位のモル比、25℃における粘度及び重量平均分子量(Mw)を表1に示す。
合成されたシルセスキオキサン誘導体1~13 1質量部に対し、2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン0.03質量部を添加し、混合物を自転・公転ミキサーで攪拌することで光硬化性組成物1~13(P1~P13)をそれぞれ調製した。光硬化性組成物1~13では、シルセスキオキサン誘導体1~13の合成の際に溶媒等が留去により除去されているため、光硬化性組成物1~13は実質的に溶媒を含んでいない。
Anton Paar社製MCR-301に浜松ホトニクス社製Lightning cure LC5を接続した。前記のように調製した各光硬化性組成物にせん断歪みをかけながら紫外線(UV)を照射することにより、UV照射時の貯蔵弾性率の上昇の挙動を記録し、各光硬化性組成物のUV硬化速度(UV硬化性)を評価した。8mmφパラレルプレートを用い、25℃及び窒素気流中の条件下にて、1Hzで歪み0.05%を加えることにより各光硬化性組成物の貯蔵弾性率を測定した。UV光源として高圧水銀ランプを使用し、熱線カットフィルター・バンドパスフィルター・減光フィルターを介することで、365nmの短波長のみを各光硬化性組成物に照射した。このときのUV照射強度は10mW/cm2であった。UV硬化性は、UVを10秒間照射したときの各光硬化性組成
物の貯蔵弾性率の値に基づいて、以下の基準で評価した。A>B>Cの順でUV硬化性に優れる。実験結果を表1に示す。
-評価基準-
A:5.0×106Pa以上
B:1.0×106Pa以上5.0×106Pa未満
C:1.0×106Pa未満
PET(ポリエチレンテレフタレート)フィルム、又はアセトンで洗浄したSPCC鋼板(冷間圧延鋼板)に、前記のようにして調製した光硬化性組成物1~13をそれぞれ塗布した。具体的には、PETフィルムを用いた場合はNo.10のバーコーターを用い、SPCC鋼板を用いた場合は、No.4のバーコーターを用いて各光硬化性組成物を塗布した後、塗布された各光硬化性組成物に以下の条件にて紫外線を照射して硬化し、光硬化膜を作製した。PETフィルムを用いた場合での光硬化膜の膜厚は約10μmであり、SPCC鋼板を用いた場合での光硬化膜の膜厚は約5μmであった。
[紫外線照射条件]
ランプ:高圧水銀灯
ランプ高さ:10cm
コンベアスピード:5.75m/min
1パスあたりの積算光量:360mJ/cm2(UV-A)
雰囲気:大気中
パス回数:10回
前述のようにして作製した光硬化膜に対し、JIS K5600-5-4に則って鉛筆硬度試験を行った。基材としてPETフィルムを用いた場合には3Hの鉛筆を用い、SPCC鋼板を基材として用いた場合には8Hの鉛筆を用いてそれぞれ鉛筆硬度試験を行った。引っかき試験を各光硬化膜に対して10回実施し、光硬化膜に欠陥が生じなかった回数を%で示した。この%値が高いほど、光硬化膜の硬度が高いことを意味する。実験結果を表1に示す。
さらに、実施例1~実施例8で得られたシルセスキオキサン誘導体は、比較例4と比較して25℃における粘度が同程度であり、かつ硬度に優れる光硬化膜が製造可能であった。
また、実施例1~実施例8で得られたシルセスキオキサン誘導体は、比較例5と比較して25℃における粘度が低く、かつ硬度に優れる光硬化膜が製造可能であった。
本明細書に記載された全ての文献、特許出願、及び技術規格は、個々の文献、特許出願、及び技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書中に参照により取り込まれる。
Claims (9)
- 下記式(1)で表されるシルセスキオキサン誘導体。
〔式(1)中、R1及びR2は、それぞれ独立に炭素原子数1~10のアルキレン基、炭素原子数3~10のシクロアルキレン基、炭素原子数6~10のアリーレン基又は炭素原子数7~12のアラルキレン基であり、R3は炭素原子数1~6のアルキル基であり、R4及びR5は、それぞれ独立に水素原子、炭素原子数1~20の飽和若しくは不飽和のアルキル基、炭素原子数3~8の飽和若しくは不飽和のシクロアルキル基、炭素原子数6~20のアリール基又は炭素原子数7~20のアラルキル基であり、R6はエチレン性不飽和結合及び炭素炭素三重結合の少なくとも一方を有する炭素原子数2~12の有機基であり、R7及びR8はそれぞれ独立に炭素原子数1~10のアルキル基、炭素原子数6~10のアリール基又は炭素原子数7~10のアラルキル基であり、複数存在するR5は互いに同一でも異なっていてもよく、複数存在するR7は互いに同一でも異なっていてもよく、複数存在するR8は互いに同一でも異なっていてもよく、R1~R8は、それぞれ独立に置換基又はハロゲン原子で構造の一部が置換されていてもよく、yは正の数であり、t、u、v、w、x及びzはそれぞれ独立に0又は正の数であり、u及びvの少なくともいずれか1つは正の数である。〕 - 前記式(1)中、t、x及びzは0であり、0.01≦y/(u+v+w)≦0.5である、請求項1に記載のシルセスキオキサン誘導体。
- 前記式(1)中、u及びvはそれぞれ独立に正の数であり、0<v/u≦1である、請求項1又は請求項2に記載のシルセスキオキサン誘導体。
- 25℃における粘度は、10mPa・s~4,000mPa・sである、請求項1~請求項3のいずれか1項に記載のシルセスキオキサン誘導体。
- 請求項1~請求項4のいずれか1項に記載のシルセスキオキサン誘導体と重合開始剤とを含む、硬化性組成物。
- 請求項5に記載の硬化性組成物からなる、ハードコート剤。
- 請求項5に記載の硬化性組成物を硬化させてなる、硬化物。
- 請求項6に記載のハードコート剤を硬化させてなる、ハードコート。
- 請求項8に記載のハードコートを備える基材。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020247019283A KR20240112863A (ko) | 2021-12-01 | 2022-12-01 | 실세스퀴옥산 유도체, 경화성 조성물, 하드 코팅제, 경화물, 하드 코팅 및 기재 |
JP2023565095A JPWO2023100991A1 (ja) | 2021-12-01 | 2022-12-01 | |
CN202280079602.3A CN118339216A (zh) | 2021-12-01 | 2022-12-01 | 倍半硅氧烷衍生物、固化性组合物、硬涂层剂、固化物、硬涂层及基材 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021-195433 | 2021-12-01 | ||
JP2021195433 | 2021-12-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023100991A1 true WO2023100991A1 (ja) | 2023-06-08 |
Family
ID=86612356
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2022/044462 WO2023100991A1 (ja) | 2021-12-01 | 2022-12-01 | シルセスキオキサン誘導体、硬化性組成物、ハードコート剤、硬化物、ハードコート及び基材 |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPWO2023100991A1 (ja) |
KR (1) | KR20240112863A (ja) |
CN (1) | CN118339216A (ja) |
WO (1) | WO2023100991A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023238835A1 (ja) * | 2022-06-10 | 2023-12-14 | 東亞合成株式会社 | シルセスキオキサン誘導体及びその製造方法、硬化性組成物、ハードコート剤、硬化物、ハードコート、並びに、基材 |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60219229A (ja) * | 1984-03-27 | 1985-11-01 | ワツカー‐ヒエミー・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | オルガノ(ポリ)シロキサンおよびこの種のオルガノ(ポリ)シロキサンを含有する、光の照射により架橋可能な材料 |
JPH07173178A (ja) * | 1993-11-04 | 1995-07-11 | Shin Etsu Chem Co Ltd | 有機けい素化合物 |
JPH0873593A (ja) * | 1994-09-08 | 1996-03-19 | Showa Denko Kk | ポリオルガノシロキサン及びその製造方法 |
JPH0892374A (ja) * | 1994-09-19 | 1996-04-09 | Showa Denko Kk | ポリシルセスキオキサン及びそのビニル重合体 |
JPH08113648A (ja) * | 1994-10-18 | 1996-05-07 | Showa Denko Kk | 末端シリル化ポリシルセスキオキサンの製造法 |
JPH08253590A (ja) * | 1995-03-16 | 1996-10-01 | Shin Etsu Chem Co Ltd | (メタ)アクリロイルオキシル基含有オルガノポリシロキサンの製造方法 |
JPH08311139A (ja) * | 1995-03-16 | 1996-11-26 | Shin Etsu Chem Co Ltd | 光硬化性オルガノポリシロキサン組成物 |
JP2009167325A (ja) * | 2008-01-17 | 2009-07-30 | Nippon Steel Chem Co Ltd | シラノール基含有硬化性籠型シルセスキオキサン化合物およびこれを用いた共重合体並びにそれらの製造方法 |
JP2011195750A (ja) * | 2010-03-23 | 2011-10-06 | Nippon Steel Chem Co Ltd | 硬化型樹脂組成物及びこれから得られる成形体 |
CN102690416A (zh) * | 2012-06-13 | 2012-09-26 | 江苏宏达新材料股份有限公司 | 一种高折射率硅树脂及其制备方法 |
CN103554169A (zh) * | 2013-10-29 | 2014-02-05 | 烟台德邦先进硅材料有限公司 | 一种用于uv固化树脂的有机硅丙烯酸酯和有机硅甲基丙烯酸酯单体的制备方法 |
CN103554500A (zh) * | 2013-10-29 | 2014-02-05 | 烟台德邦先进硅材料有限公司 | 一种uv光固化的聚硅氧烷及其制备方法 |
CN106146850A (zh) * | 2016-07-05 | 2016-11-23 | 山东省科学院新材料研究所 | 一种加成型有机硅浸渍树脂用增粘剂及其制备方法 |
CN107236482A (zh) * | 2017-05-16 | 2017-10-10 | 深圳市锦航光电科技有限公司 | 一种多臂led封装胶补强助剂及其制备方法 |
CN112341962A (zh) * | 2020-11-02 | 2021-02-09 | 新安天玉有机硅有限公司 | 一种硅橡胶用底涂剂及其制备方法 |
CN112759997A (zh) * | 2021-02-05 | 2021-05-07 | 东莞市贝特利新材料有限公司 | 一种有机硅底层涂料组合物及其制备方法 |
CN112979954A (zh) * | 2019-12-17 | 2021-06-18 | 深圳新宙邦科技股份有限公司 | 发光器件封装材料及其合成方法、封装胶 |
-
2022
- 2022-12-01 JP JP2023565095A patent/JPWO2023100991A1/ja active Pending
- 2022-12-01 CN CN202280079602.3A patent/CN118339216A/zh active Pending
- 2022-12-01 KR KR1020247019283A patent/KR20240112863A/ko unknown
- 2022-12-01 WO PCT/JP2022/044462 patent/WO2023100991A1/ja active Application Filing
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60219229A (ja) * | 1984-03-27 | 1985-11-01 | ワツカー‐ヒエミー・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | オルガノ(ポリ)シロキサンおよびこの種のオルガノ(ポリ)シロキサンを含有する、光の照射により架橋可能な材料 |
JPH07173178A (ja) * | 1993-11-04 | 1995-07-11 | Shin Etsu Chem Co Ltd | 有機けい素化合物 |
JPH0873593A (ja) * | 1994-09-08 | 1996-03-19 | Showa Denko Kk | ポリオルガノシロキサン及びその製造方法 |
JPH0892374A (ja) * | 1994-09-19 | 1996-04-09 | Showa Denko Kk | ポリシルセスキオキサン及びそのビニル重合体 |
JPH08113648A (ja) * | 1994-10-18 | 1996-05-07 | Showa Denko Kk | 末端シリル化ポリシルセスキオキサンの製造法 |
JPH08253590A (ja) * | 1995-03-16 | 1996-10-01 | Shin Etsu Chem Co Ltd | (メタ)アクリロイルオキシル基含有オルガノポリシロキサンの製造方法 |
JPH08311139A (ja) * | 1995-03-16 | 1996-11-26 | Shin Etsu Chem Co Ltd | 光硬化性オルガノポリシロキサン組成物 |
JP2009167325A (ja) * | 2008-01-17 | 2009-07-30 | Nippon Steel Chem Co Ltd | シラノール基含有硬化性籠型シルセスキオキサン化合物およびこれを用いた共重合体並びにそれらの製造方法 |
JP2011195750A (ja) * | 2010-03-23 | 2011-10-06 | Nippon Steel Chem Co Ltd | 硬化型樹脂組成物及びこれから得られる成形体 |
CN102690416A (zh) * | 2012-06-13 | 2012-09-26 | 江苏宏达新材料股份有限公司 | 一种高折射率硅树脂及其制备方法 |
CN103554169A (zh) * | 2013-10-29 | 2014-02-05 | 烟台德邦先进硅材料有限公司 | 一种用于uv固化树脂的有机硅丙烯酸酯和有机硅甲基丙烯酸酯单体的制备方法 |
CN103554500A (zh) * | 2013-10-29 | 2014-02-05 | 烟台德邦先进硅材料有限公司 | 一种uv光固化的聚硅氧烷及其制备方法 |
CN106146850A (zh) * | 2016-07-05 | 2016-11-23 | 山东省科学院新材料研究所 | 一种加成型有机硅浸渍树脂用增粘剂及其制备方法 |
CN107236482A (zh) * | 2017-05-16 | 2017-10-10 | 深圳市锦航光电科技有限公司 | 一种多臂led封装胶补强助剂及其制备方法 |
CN112979954A (zh) * | 2019-12-17 | 2021-06-18 | 深圳新宙邦科技股份有限公司 | 发光器件封装材料及其合成方法、封装胶 |
CN112341962A (zh) * | 2020-11-02 | 2021-02-09 | 新安天玉有机硅有限公司 | 一种硅橡胶用底涂剂及其制备方法 |
CN112759997A (zh) * | 2021-02-05 | 2021-05-07 | 东莞市贝特利新材料有限公司 | 一种有机硅底层涂料组合物及其制备方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023238835A1 (ja) * | 2022-06-10 | 2023-12-14 | 東亞合成株式会社 | シルセスキオキサン誘導体及びその製造方法、硬化性組成物、ハードコート剤、硬化物、ハードコート、並びに、基材 |
Also Published As
Publication number | Publication date |
---|---|
KR20240112863A (ko) | 2024-07-19 |
CN118339216A (zh) | 2024-07-12 |
JPWO2023100991A1 (ja) | 2023-06-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5826341B2 (ja) | 硬化物の製造方法 | |
JP5685571B2 (ja) | 硬化性組成物 | |
JP5640381B2 (ja) | アルコキシシランの縮合物を含む活性エネルギー線硬化型コーティング剤組成物 | |
JP5477299B2 (ja) | マレイミド基で表面修飾した無機酸化物微粒子を含む硬化型組成物 | |
JP5886420B2 (ja) | ラジカル架橋性基を有するポリシロキサン組成物 | |
JP5051383B2 (ja) | (メタ)アクリル変性シロキサン化合物及びそれを含有する硬化性組成物 | |
KR20130132477A (ko) | 불소-함유 고분지 중합체를 포함하는 코팅용 경화성 조성물 | |
JP5907588B2 (ja) | シルセスキオキサン化合物及びこれを含むコーティング組成物 | |
US20140323677A1 (en) | Thermal-shock-resistant cured product and method for producing same | |
EP3970967A1 (en) | Radiation curable organopolysiloxane composition, and release sheet | |
WO2023100991A1 (ja) | シルセスキオキサン誘導体、硬化性組成物、ハードコート剤、硬化物、ハードコート及び基材 | |
WO2023100992A1 (ja) | シルセスキオキサン誘導体、硬化性組成物、硬化物及び基材 | |
WO2023238835A1 (ja) | シルセスキオキサン誘導体及びその製造方法、硬化性組成物、ハードコート剤、硬化物、ハードコート、並びに、基材 | |
JP7276183B2 (ja) | 活性エネルギー線硬化性組成物、コーティング剤、および被膜物品 | |
WO2024122417A1 (ja) | ハードコート層付き積層体の製造方法、及びハードコート層付き積層体 | |
JP2022182542A (ja) | 光硬化性樹脂組成物およびその用途 | |
WO2024122416A1 (ja) | ハードコート層付き積層体の製造方法 | |
TW202432261A (zh) | 附有硬塗層之積層體的製造方法、及附有硬塗層之積層體 | |
JP2012223910A (ja) | 積層体およびその製造方法 | |
TWI851733B (zh) | 含氟硬化性組成物及物品 | |
TW202432260A (zh) | 附有硬塗層之積層體的製造方法 | |
JP2012116173A (ja) | 保護被膜を有する積層体 | |
WO2023120495A1 (ja) | 光硬化性シリコーン樹脂組成物、その硬化物 | |
WO2023238836A1 (ja) | シルセスキオキサン誘導体及びその製造方法、硬化性組成物、ハードコート剤、硬化物、ハードコート、並びに、基材 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22901421 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 202280079602.3 Country of ref document: CN |
|
ENP | Entry into the national phase |
Ref document number: 2023565095 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20247019283 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |