CN106232684B - Resin combination for transparent plastic substrate - Google Patents
Resin combination for transparent plastic substrate Download PDFInfo
- Publication number
- CN106232684B CN106232684B CN201580021114.7A CN201580021114A CN106232684B CN 106232684 B CN106232684 B CN 106232684B CN 201580021114 A CN201580021114 A CN 201580021114A CN 106232684 B CN106232684 B CN 106232684B
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- Prior art keywords
- unsubstituted
- substituted
- resin
- alkyl
- resin combination
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 99
- 239000011347 resin Substances 0.000 title claims abstract description 99
- 239000000758 substrate Substances 0.000 title claims abstract description 31
- 229920003023 plastic Polymers 0.000 title claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 238000001029 thermal curing Methods 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 12
- -1 bicyclic alkane Chemical class 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000012745 toughening agent Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 230000003252 repetitive effect Effects 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 150000001260 acyclic compounds Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 238000006886 vinylation reaction Methods 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 150000002921 oxetanes Chemical class 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 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 claims description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002170 ethers Chemical group 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 description 18
- 229920000647 polyepoxide Polymers 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 239000010408 film Substances 0.000 description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 7
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000010954 inorganic particle Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000011258 core-shell material Substances 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 229920002313 fluoropolymer Polymers 0.000 description 5
- 239000004811 fluoropolymer Substances 0.000 description 5
- 238000013007 heat curing Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 229910004749 OS(O)2 Inorganic materials 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- PKDCQJMRWCHQOH-UHFFFAOYSA-N triethoxysilicon Chemical compound CCO[Si](OCC)OCC PKDCQJMRWCHQOH-UHFFFAOYSA-N 0.000 description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
- 208000037656 Respiratory Sounds Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N alpha-hydroxyacetone Natural products CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 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
- 229940106691 bisphenol a Drugs 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 2
- 150000004292 cyclic ethers Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BRXKVEIJEXJBFF-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-3-methylbutane-1,4-diol Chemical compound OCC(C)C(CO)(CO)CO BRXKVEIJEXJBFF-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
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-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
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XXJWUZQJPJLUNE-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl 3-methylbut-2-enoate Chemical compound CC(=CC(=O)OCCOCCOCCOCCO)C XXJWUZQJPJLUNE-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- QFRHTANKIYQYLO-UHFFFAOYSA-N 2-ethyl-2-methylimidazole Chemical class CCC1(C)N=CC=N1 QFRHTANKIYQYLO-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- SUXFTQHLBSWETF-UHFFFAOYSA-N methyl 2,3-dimethylbut-2-enoate Chemical compound COC(=O)C(C)=C(C)C SUXFTQHLBSWETF-UHFFFAOYSA-N 0.000 description 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
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- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
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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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
Abstract
Provided is a kind of resin combination for transparent plastic substrate.The resin combination includes the silsesquioxane resin that (A) is indicated by formula 1:
Description
Technical field
The present invention relates to a kind of resin combinations for transparent plastic substrate, are suitable for system more particularly, to one kind
Make the resin combination of the transparent plastic substrate with high flexible and very good mechanical properties.
Background technique
As modern society enters an advanced information age, electronical display industry is just become more and more important.Recently
Technology/product development of flat-panel monitor (FPD), have been based on high quality Findings and over a large area manufacture achieve into
Exhibition.Price and the flexible key factor for being predicted to be future display industry development.In current information guiding society, greatly
Type, flat and multifunction display are devices indispensable in vision industry.It also needs to record and exchange whenever and wherever possible information.
In this case it is necessary to display easy to carry and light-weight.Existing cathode-ray tube is unable to satisfy these requirements, because
For their very heavy and not Portable belts.Therefore, many researchs focus on the flat-panel monitor that exploitation can manufacture over a large area
(FPD) and the equally ultralight flexible display of sensitive paper.
Current display glass substrate has high transparency, transmissivity and pencil hardness (>=7H), and shows good
Soil resistance and chemical resistance, therefore be suitable for display industry.However, current display glass substrate is when being hit
It is brittle, therefore, it is difficult to use, in the flexible display that especially arouses attention on as next generation display.
Summary of the invention
The object of the present invention is to provide be suitable for manufacture to have good heat resistance, high-transmission rate, high rigidity, good scratch resistance
Property and improvement impact resistance flexible transparent substrate resin combination.
A scheme according to the present invention provides a kind of resin combination for transparent plastic substrate, comprising:
(A) silsesquioxane resin indicated by formula 1:
Wherein R1、R2And R3The C for respectively standing alone as singly-bound, being substituted or being unsubstituted1-C6Stretch alkyl, be substituted or without
Substituted C1-C6The C that-O- stretches alkyl or is substituted or is unsubstituted2-C12It stretches alkyl-O- and stretches alkyl,
Each R1aAll stand alone as the C for being substituted or being unsubstituted1-C12Alkyl or the C for being substituted or being unsubstituted3-C18Ring
Alkyl,
Each R2aAll stand alone as C being substituted or be unsubstituted, with ethylenic linkage2-C12Alkyl,
Each R3aAll stand alone as be substituted or be unsubstituted containing C2-C10Cyclic ether group,
The integer that l is 2 to 500, and
M and n respectively stands alone as 0 to 500 integer, on condition that at least one in m and n is not 0；And
(B) photopolymerization initiator or thermal curing agents.
Further scheme according to the present invention, which provides, a kind of to be formed and is had in 5 μm to 5,000 μm models using the composition
The overlay of thickness in enclosing.
Another scheme according to the present invention provides a kind of substrate including the overlay.
There is high transmissivity, pliability and hardness for the resin combination of transparent plastic substrate according to the present invention, and
Show good heat resistance, scratch resistance and impact resistance.Due to these advantages, resin combination of the invention can be applied to
Various hard coat films, display protection window and the substrate for flexible device.
Specific embodiment
It will be described in the present invention now.
Term " alkyl " used herein is intended to include straight chain, branch and cyclic hydrocarbon group.Term " stretching alkyl ", which refers to, to spread out
It is born from the bivalent group of alkyl.For example, stretch alkyl include methylene, stretch ethyl, stretch isobutyl group, stretch cyclohexyl, cyclopenta stretches second
Base, 2- stretch acrylic and 3- stretches butynyl.
Unless otherwise stated, term " miscellaneous alkyl " itself or combined with another term mean it is former by the carbon of the number
Stable straight chain, branch composed by sub and one or more hetero atoms selected from the group as composed by O, N, P, Si and S,
Cyclic hydrocarbon group or combinations of the above, and wherein nitrogen, phosphorus and sulphur atom can be optionally oxidized, and nitrogen heteroatom can be with
Optionally it is quaternized.Similarly, term " miscellaneous to stretch alkyl " refers to the bivalent group derived from miscellaneous alkyl.
Unless otherwise stated, otherwise term " aryl " means the aromatics hydrocarbon substituent of how unsaturated, can be monocycle or
Polycyclic (1 to 3 ring) for being fused together or being covalently attached.Term " heteroaryl ", which refers to, is selected from N, O and S containing one to four
The aryl (or ring) of hetero atom (in the case where polycyclic in each individual ring), wherein nitrogen and sulphur atom are optionally by oxygen
Change, and nitrogen-atoms is optionally quaternized.Heteroaryl can be connected to the rest part of molecule by carbon or hetero atom.Aryl
Non-limiting example with heteroaryl includes phenyl, 1- naphthalene, 2- naphthalene, 4- xenyl, 1- pyrrole radicals, 2- pyrrole radicals, 3- pyrrole
Cough up base, 3- pyrazolyl, 2- imidazole radicals, 4- imidazole radicals, pyrroleBase, 2- oxazolyl, 4- oxazolyl, 2- phenyl -4- oxazolyl, 5- are disliked
Oxazolyl, 3- isoxazolyl, 4- isoxazolyl, 5- isoxazolyl, 2- thiazolyl, 4- thiazolyl, 5- thiazolyl, 2- furyl, 3-
Furyl, 2- thienyl, 3- thienyl, 2- pyridyl group, 3- pyridyl group, 4- pyridyl group, 2- pyrimidine radicals, 4- pyrimidine radicals, 5- benzo
Thiazolyl, purine radicals, 2- benzimidazolyl, 5- indyl, 1- isoquinolyl, 5- isoquinolyl, 2- quinolineQuinoline base, 5- quinoline
Quinoline base, 3- quinolyl and 6- quinolyl.The substituent group of each in above-mentioned aryl and heteroaryl is to be selected to be subjected to by following
Group composed by substituent group.Term " stretching aryl " and " miscellaneous to stretch aryl " refer respectively to the bivalent group of aryl and heteroaryl.
In the statement of " be substituted or be unsubstituted " described herein, term " being substituted " mean one in hydrocarbon or
More hydrogen atoms are substituted by identical or different substituent group each independently.
Substituent group appropriate includes but is not limited to-Ra,-halogen ,-O-,=O ,-ORb、-SRb、-S-,=S ,-NRcRc,=
NRb,=N-ORb, trihalomethyl ,-CF3、-CN、-OCN、-SCN、-NO、-NO2,=N2、-N3、-S(O)2Rb、-S(O)2NRb、-S
(O)2O-、-S(O)2ORb、-OS(O)2Rb、-OS(O)2O-、-OS(O)2ORb、-P(O)(O-)2、-P(O)(ORb)(O-)、-P(O)
(ORb)(ORb)、-C(O)Rb、-C(S)Rb、-C(NRb)Rb、-C(O)O-、-C(O)ORb、-C(S)ORb、-C(O)NRcRc、-C(NRb)
NRcRc、-OC(O)Rb、-OC(S)Rb、-OC(O)O-、-OC(O)ORb、-OC(S)ORb、-NRbC(O)Rb、-NRbC(S)Rb、-NRbC
(O)O-、-NRbC(O)ORb、-NRbC(S)ORb、-NRbC(O)NRcRc、-NRbC(NRb)RbAnd-NRbC(NRb)NRcRc, wherein Ra
It is selected from the group as composed by alkyl, naphthenic base, miscellaneous alkyl, cycloheteroalkyl, aryl, aralkyl, heteroaryl and heteroaryl alkyl
Group；Each RbAll stand alone as hydrogen or Ra；Each RcAll stand alone as Rb, on condition that two RcGroup nitrogen-atoms in connection can be with
It is formed together 4-, 5-, 6- or 7- membered cycloheteroalkyl group, and 1 to 4 can be optionally included selected from the group as composed by O, N and S
Identical or different other hetero atoms of group.As specific example ,-NRcRcMean to include-NH2,-NH- alkyl, N- Pyrrolizidine
Base and N- forint base.As another example, the alkyl being substituted means to include that-stretch alkyl-O- alkyl ,-it is miscellaneous to stretch alkyl-
Aryl ,-stretch alkyl-cycloheteroalkyl ,-stretch alkyl-C (O) ORb,-stretch alkyl-C (O) NRbRbAnd-CH2-CH2-C(O)-CH3.It should
One or more substituent group atoms connected to them can be optionally formed together including naphthenic base and cycloheteroalkyl
Cyclic rings.
One embodiment of the present of invention provide it is a kind of for transparent plastic substrate, including the combination of silsesquioxane resin
Object.Specifically, which may include (A) silsesquioxane resin, (B) photopolymerization initiator or thermal curing agents,
(C) with the polyfunctional compound of vinylation unsaturated bond, (D) toughener, (methyl) the propylene acidification of (E) for viscosity adjustment
Close object or organic solvent, and (F) additive.The resin combination can optionally further comprise (G) inorganic particle.
It is the more detailed description of the individual components about the resin combination below.
(A) silsesquioxane resin
Silsesquioxane resin is the scalariform silsesquioxane polymer indicated by formula 1:
In one embodiment, silsesquioxane resin has silsesquioxane structure in main chain, and may include
Photosensitive functional group, such as photocuring allyl, vinyl or acrylic acid groups.The presence of photosensitive functional group allows in photocuring group
It closes and uses silsesquioxane resin in object.In a further embodiment, silsesquioxane resin has silicon sesquialter in main chain
Oxygen alkyl structure, and may include cyclic ether group, such as can be thermally cured epoxy group.The presence of cyclic ether group allows can thermosetting
Change and uses silsesquioxane resin in composition.Silsesquioxane resin may include that various other functional groups are required to realize
Physical property.
It is well known that silsesquioxane resin has and chemical structure as category of glass.Due to this structure, silsesquioxane
Resin can show good heat resistance, high-transmission rate, high rigidity and improved scratch resistance, and above-mentioned is all the characteristic of glass.
In formula 1, R1、R2And R3The C that singly-bound can be respectively stood alone as, be substituted or be unsubstituted1-C6It stretches alkyl, be substituted
Or the C being unsubstituted1-C6The C that-O- stretches alkyl or is substituted or is unsubstituted2-C12It stretches alkyl-O- and stretches alkyl.
In formula 1, each R1aThe C for being substituted or being unsubstituted can all be stood alone as1-C12Alkyl is substituted or without taking
The C in generation3-C18Cyclic hydrocarbon radical.
Including R1And R1aRepetitive unit (I) can be single form, but it is preferred that various forms of repetitive units
Combination, is controlled in required level for the physical property of silsesquioxane resin.For example, oligomeric silsesquioxane polymer can contain
There are three types of various forms of repetitive units (I) ', (I) " and (I) " ' combination as repetitive unit (I), wherein R1And R1aGroup
It can be the same or different from each other.
The C for being substituted or being unsubstituted1-C12Alkyl can be such as methyl, ethyl, propyl, butyl, hexyl or octyl.
The C for being substituted or being unsubstituted3-C18Cyclic hydrocarbon radical can be naphthenic base, bicyclic alkyl, aryl or heteroaryl.Cyclic hydrocarbon
Base can include the hetero atom or at least one double bond of at least one such as N, P, O or S in the structure.Preferably, it is substituted
Or the C being unsubstituted3-C18Cyclic hydrocarbon radical is to be selected from by but be not limited toComposed group.
The C for being substituted or being unsubstituted1-C12Alkyl makes oligomeric silsesquioxane polymer have enough flexible and allows to gather
Silsesquioxane polymer has glass transition temperature appropriate.The C for being substituted or being unsubstituted3-C18Cyclic hydrocarbon radical improves photosensitive
The heat resistance and hardness of resin combination.
In formula 1, each R2aIt is all the photosensitive function that may participate in curing reaction when being exposed to light in the presence of light initiator
Base, and stand alone as and be substituted or be unsubstituted C at least one vinylation unsaturated bond2-C12Alkyl.Photosensitive functional group
It can be the alkyl containing end 3- methylacryloyl, 3- acryloyl group, vinyl or allyl, specific example includes 3-
Methacryloxypropyl, 3- acryloxypropyl, 3- methylacryloyl, 3- acryloyl group, vinyl and allyl.
In formula 1, each R3aAll be in the presence of thermal curing agents heat when may participate in curing reaction functional group and solely
It stands to be substituted or being unsubstituted containing C2-C10Cyclic ether group.What is be substituted or be unsubstituted contains C2-C10Cyclic ether group can be
Alkyl containing terminal glycidyl group, 2- (3,4- epoxycyclohexyl) or oxetanes -3- base, specific example includes 3-
Glycidoxypropyl, 3- glycidyl, 2- (3,4- epoxycyclohexyl) ethyl, 3- ethyl -3- [3- propoxy methyl]
Oxetanyl and oxetanes -3- ylmethyl.Preferably, what is be substituted or be unsubstituted contains C2-C10Cyclic ether group
Contain epoxy group.
In formula 1, l is 2 to 500 integer, and m and n respectively stand alone as 0 to 500 integer, on condition that at least one in m and n
A is not 0.
The ratio of repetitive unit (I), (II) and (III) can be respectively 1 to 90 mole of %, 0 in silsesquioxane resin
To 30 moles of % and 0 to 30 mole of %.Within the scope of these, it can be ensured that the flexibility manufactured using silsesquioxane resin is saturating
The excellent physical properties of bright plastic basis material.
The weight average molecular weight of silsesquioxane resin is preferably 2,000 to 100,000.If silsesquioxane resin
Average molecular weight less than 2,000, then be difficult to manufacture plastic basis material.Meanwhile if the weight average of silsesquioxane resin divides
Son amount is more than 100,000, then the stickiness of resin combination is got higher, and asks to generate in the treatment process of manufacture plastic basis material
Topic.The polydispersity index of silsesquioxane resin is preferably 1 to 10.It is more than 10 silsesquioxane using average polydispersity index
Resin may cause the problem of substrate flatness.
In formula 1, m, which can not be 0, n, can be 0.That is, repetitive unit (II) may exist and repetitive unit
(III) it can be not present in silsesquioxane resin.In this case, silsesquioxane resin can be used for light-cured resin
In composition.Alternatively, m can be 0, and n can not be 0 in formula 1.That is, repetitive unit (II) can be not present
And repetitive unit (III) can reside in silsesquioxane resin.In this case, silsesquioxane resin can be used for
In thermally curable resin composition.In some cases, repetitive unit (II) and (III) can coexist in silsesquioxane resin
In.In these cases, it can be manufactured after photocuring by heat cure with the substrate for improving heat resistance.
Total weight based on resin combination, the amount of preferably including of silsesquioxane resin are 5 to 80 weight %.If silicon
The content of sesquioxyalkane resin is less than the lower limit defined above, then is likely difficult to the substrate that manufacture has required thickness.Meanwhile it is false
The content for making silsesquioxane resin is more than the upper limit defined above, then resin combination may be full-bodied, make it difficult to
Manufacture substrate.
(B) photopolymerization initiator or thermal curing agents
The photopolymerization initiator of resin combination according to the present invention is with visible light, ultraviolet light, extreme ultraviolet light, electrification
The ingredient that can cause the active specy of silsesquioxane resin polymerization is generated when particle radiation, X-ray etc. are irradiated.
For example, photopolymerization initiator can be selected from: oxime ester compound, united imidazole, benzoin compound, acetophenone
Compound, benzophenone cpd, α-dione compounds, multicore naphtoquinone compounds, phosphine compound and triaizine compounds.Wherein, benzene
Ethanone compounds or oxime ester compound are preferred.
Oxime ester compound can be such as 1- [9- ethyl -6- (2- methyl benzoyl) -9H- carbazole -3- base] -1- (O-
Acetyl group oxime) and 1,3- octadione- 1 [(4- thiophenyl) phenyl] -2- benzoyl oximes.
Acetophenone compound can be such as alpha-hydroxyacetone compounds, α-saddle base ketone compound and other acetophenone chemical combination
Object.
The specific example of alpha-hydroxyacetone compounds includes 1- phenyl -2- hydroxy-2-methyl propyl- 1- ketone, 1- (4- cumene
Base) -2- hydroxy-2-methyl propyl- 1- ketone, 4- (2- hydroxyl-oxethyl) phenyl-(2- hydroxyl -2- propyl) ketone and 1- hydroxy cyclohexylphenyl
Base phenyl ketone.α-amido ketone compound specific example includes 2- methyl-1-[4- (methyl mercapto) phenyl]-2- forint propyl- 1-
Ketone and 2- Benzyl base -2- dimethylamino -1- (4- forint phenyl)-butanone -1.The example of other acetophenone compounds includes 2,2-
Dimethoxy-acetophenone, 2,2- diethoxy acetophenone and 2,2- dimethoxy -2- phenyl acetophenone.These acetophenone chemical combination
Object can be used alone or use as wherein two or more mixture.Facilitated further using acetophenone compound
Improve thin film strength.
The specific example of united imidazole includes bis- (2- chlorphenyl) -4,4', 5,5'- tetra- (the 4- carbethoxyl group benzene of 2,2'-
Base) -1,2'- bisglyoxaline, 2,2'- bis- (2- bromophenyl) -4,4', 5,5'- tetra- (4- carbethoxy phenyl) -1,2'- bisglyoxalines, 2,
Bis- (2- chlorphenyl) -4,4', the 5,5'- tetraphenyl -1,2'- bisglyoxalines of 2'-, 2,2'- bis- (2,4 dichloro benzene base) -4,4', 5,5'-
Bis- (2,4,6- trichlorophenyl) -4,4', the 5,5'- tetraphenyl -1,2'- bisglyoxalines of tetraphenyl -1,2'- bisglyoxaline, 2,2'-, 2,2'-
Bis- (2- bromophenyl) -4,4', 5,5'- tetraphenyl -1,2'- bisglyoxalines, 2,2'- bis- (2,4- dibromo phenyl) -4,4', 5,5'- tetra-
Phenyl -1,2'- bisglyoxaline and bis- (2,4,6- tribromo phenyl) -4,4', the 5,5'- tetraphenyl -1,2'- bisglyoxalines of 2,2'-.
In these imidazolium compounds, 2,2'- bis- (2- chlorphenyls) -4,4', 5,5'- tetraphenyl -1,2'- bisglyoxalines, 2,
Bis- (2,4 dichloro benzene base) -4,4', the 5,5'- tetraphenyl -1,2'- bisglyoxalines of 2'- and bis- (the 2,4,6- trichlorophenyls) -4 of 2,2'-,
4', 5,5'- tetraphenyl -1,2'- bisglyoxalines are preferred, 2,2'- bis- (2,4- dichlorophenyls) -4,4', 5,5'- tetraphenyl -1,
2'- bisglyoxaline is particularly preferred.
Based on the silsesquioxane resin of 100 parts by weight, the content of photopolymerization initiator is 1 to 30 parts by weight, preferably 5
To 20 parts by weight.If the content of photopolymerization initiator is less than the lower limit defined above, then it is less likely to occur to solidify.Meanwhile it is false
The content for making photopolymerization initiator is more than the upper limit defined above, then may precipitate since the dissolubility after solidifying is low.
Thermal curing agents are used to solidify the compound with epoxy group.Thermal curing agents can be commonly used in cured epoxy resin
Any curing agent.Thermal curing agents are not particularly limited, if its can be reacted with epoxy resin and cured epoxy resin i.e.
It can.Thermal curing agents are usually the compound with phenolic hydroxyl group, compound or amine with anhydride group.
The example of appropriate compound in molecule with two or more phenolic hydroxyl groups includes phenol resol resins, first
Phenol novolac resin, phenol aralkyl resin, novolac resin, the three (hydroxy benzenes synthesized by bisphenol-A and resorcinol
Base) methane, dihydro biphenyl and polyphenol compound.The example of appropriate compound with anhydride group includes maleic anhydride, neighbour
Phthalate anhydride and pyromellitic dianhydride.The example of amine appropriate includes aromatic amine, such as m-phenylene diamine (MPD), two (aminocarbonyl phenyl) first
Alkane and two amido diphenyl sulfones.
Also other types of curing agent, including latent property amine curing ingredient can be used.Term " latent property " means cure component
It does not react but reacts rapidly if being more than the start temperature of curable epoxide reaction to realize solidification at room temperature.This allows to tie
Structure adhesive agent is easy application at room temperature or under the conditions of the mild heat of no activated firming agent.
Latent property amine appropriate includes such as guanidine, is substituted guanidine (such as methylguanidine, dimethylguanidine, trimethyl guanidine, tetramethyl
The different bisguanides of guanidine, methyl, the different bisguanides of dimethyl, the different bisguanides of tetramethyl, the different bisguanides of hexamethyl, the different bisguanides of seven methyl and dicyandiamide),
Melamine resin, guanamine derivatives (such as alkylation benzoguanamine resin, benzoguanamine resin and methoxy ethoxy
Ylmethyl benzoguanamine), cyclic tertiary amine, aromatic amine, urea (such as rubigan-N, the N- dimethyl urea (weed eradication being substituted
It is grand), 3- phenyl -1,1- dimethyl urea (fenuron), 3,4- dichlorophenyl-N, N- dimethyl urea (diuron), tertiary acrylic acid-or
Alkyl-amine (Li such as Benzyl base dimethyl amine, three (dimethyl amido) phenol, piperidines and piperidine derivative) and imdazole derivatives
(such as 2- Ethyl-2-Methyl imidazoles, N- butyl imidazole, benzimidazole, N-C1To C12Alkyl imidazole and N- Aryimidazole).This
Latent property amine can be used alone or be applied in combination a bit.
Commercially available latent property amine includes Adeca Hardener series (EH-3615, EH- from Japanese Adeka company
3842 and EH-4342S) and Ajicure from Ajinomoto Co., Japan it is serial (PN-40J).
The compound in the resin combination with epoxy group, the dosage of thermal curing agents are included in based on 100 parts by weight
For 50 to 200 parts by weight, preferably 100 to 145 parts by weight, but it is not particularly limited to this content.More specifically, every epoxide equivalent
All compounds in the resin combination with epoxy group are included in, the preferable amount of thermal curing agents is equivalent to 0.5 to 1.5
Equivalent.If the dosage of thermal curing agents is less than the lower limit defined above, then it cannot achieve sufficient solidification, having makes cured product
Toughness reduce tendency.Meanwhile if the dosage of thermal curing agents is more than the upper limit defined above, then cured product may become
Color deteriorates its color.
(C) with the polyfunctional compound of vinylation unsaturated bond
Polyfunctional compound with vinylation unsaturated bond is usually have at least two vinylation double bonds cross-linking
Unit.For example, the polyfunctional compound with vinylation unsaturated bond can be selected from: multifunctional (methyl) acrylic monomers and widow
Polymers, such as glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, two propylene of triethylene glycol
Acid esters, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethylacrylate, butanediol diformazan
Base acrylate, propylene glycol diacrylate, dimethacrylate, trimethylolpropane trimethacrylate, three hydroxyls
Trimethacrylate, tetra methylol tetraacrylate, tetra methylol propane tetramethyl acrylate, new penta
Tetrol triacrylate, new penta tetrol trimethyl acrylic ester, new penta tetra-acrylate, new penta tetrol tetramethyl acrylic acid
Ester, two new penta tetrol, five acrylate, two new penta tetrol pentamethacrylates, two new penta tetrol, six acrylate, two new penta
Tetrol hexamethacrylate, 1,6 hexanediol diacrylate, 1,6-HD dimethylacrylate and pendency epoxy two
Acrylate (cardoepoxy diacrylate)；The polyester obtained by reacting (methyl) acrylic acid with polyester prepolyer
(methyl) acrylate, the polyester prepolyer are condensed to yield by polyalcohol and unitary or polyacid；It is more by making to have
First alcohol radical and the compound of two isocyanate group react and react reaction product with (methyl) acrylic acid and the polyamine that obtains
Ester (methyl) acrylate；And the epoxy by reacting (methyl) acrylic acid with epoxy resin (methyl) acrylate
Resin, the epoxy resin such as bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, phenol or cresols
Phenolic resin varnish type epoxy resin, solvable phenol aldehyde type epoxy resin, tris-phenol type epoxy resin, polycarboxylic acids poly epihydric alcohol
Ester, poly glycidyl ester, polyalcohol poly glycidyl ester, aliphatic series or alicyclic epoxy resin, amine epoxy resin or dihydroxy benzenes
Type epoxy resin.It the use of multifunctional (methyl) acrylic monomers may be advantageous when considering the factor of such as exposure sensitive
's.
Based on the silsesquioxane resin of 100 parts by weight, polyfunctional compound is 10 to 200 parts by weight including amount, excellent
It is selected as 30 to 150 parts by weight.If the content of polyfunctional compound is less than the lower limit defined above, then the curing degree of photosensitive resin
It may be decreased, so that the composition is not suitable for manufacturing substrate.Meanwhile if the content of polyfunctional compound is more than with the upper bound
Then there is the risk that the physical property of photosensitive resin may deteriorate in the fixed upper limit.
(D) toughener
Toughener is used to enhance the toughness of solidification composition filling.Typical toughener include core-shell polymer, nitrile rubber,
And acrylate copolymer and copolymer.
Toughener can be core-shell polymer, and when core is often used butadiene polymer or copolymer, styrene polymer
Or copolymer, acrylonitrile polymer or copolymer, acrylate polymer or copolymer or combinations of the above are formed.These are poly-
Conjunction object or copolymer can be crosslinking or uncrosslinked.Some illustrative shells are using by the polymethyl of optional crosslinking
What sour methyl esters was formed.Other illustrative shells are formed using by the butadiene-styrene copolymer of optional crosslinking.
The shell of core-shell polymer is using styrene polymer or copolymer, methacrylate polymers or to be total to often
What polymers, acrylonitrile polymer or copolymer or combinations of the above were formed.Shell can further be used epoxy group, acidity or second
Acyl acetoxyl group functionalization.The functionalization of this shell can for example by with glycidyl methacrylate or acrylic acid copolymer
Or it is reacted by hydroxyl with alkyl acetoacetates acetoxyl group (such as tert-butyl acetoacetoxy groups) to complete.These functional groups are added
Shell is crosslinked with polymer substrate.
Core-shell polymer is received at least 10 nanometers, at least 20 nanometers, at least 50 nanometers, at least 100 nanometers, at least 150
Rice or at least 200 nanometers of average grain diameter.The average grain diameter of core-shell polymer can be maximum 400 nanometers, it is 500 nanometers maximum,
Maximum 750 nanometers or 1000 nanometers maximum.The average grain diameter of core-shell polymer can for example 10 to 1000 nanometers, 50 to
In 1000 nanometers, 100 to 750 nanometers or 150 to 500 nanometers of range.
Alternatively, modified epoxy can be used as toughener.Modified epoxy was primarily used in the heat cure phase
Between need to control the adhesive agent of resin flowing or need the structural material of toughness.It is because solid using the reason of modified epoxy
The silsesquioxane resin of change is susceptible to hit or be vibrated due to its low brittleness, to limit it in the knot for needing toughness
Purposes in structure material.
The necessity of modified epoxy is the high crosslink density due to the curable epoxy base of silsesquioxane resin.Though
The high crosslink density of right curable epoxy base provides many advantages and high intensity for silsesquioxane resin, but it causes silicon
The brittleness of sesquioxyalkane resin is poor.Modified epoxy is used to improve the toughness of silsesquioxane resin.Increase silsesquioxane
Other representative examples of the toughness of resin are to be introduced into soft chain segment in the main chain of curing agent and epoxy resin, add during curing
Enter reaction material to reduce crosslink density and adding liquid rubber, such as butadiene acrylonitrile (CTBN), the amine of carboxy blocking
The butadiene acrylonitrile (ATBN) and chloroprene rubber (CR) of sealing end.Improve one of the most effectual way of epoxy resin toughness
It is that rubber is added in silsesquioxane resin.According to the method, rubber grain is dispersed in silsesquioxane resin by physical
In or rubber molecule be incorporated into epoxy resin.Have been carried out a large amount of research in this respect, and epoxy resin and CTBN
Compound is commercially available at present.
Based on the silsesquioxane resin of 100 parts by weight, the preferable amount of toughener is 5 to 30 parts by weight.Usage amount is few
Hardly improve physical property in the toughener of 5 parts by weight.Meanwhile usage amount be more than 30 parts by weight toughener generate it is low hard
Degree, leads to the imbalance between scratch resistance and processability.
(E) (methyl) acyclic compound or organic solvent for viscosity adjustment
(methyl) acyclic compound for viscosity adjustment can provide the control of viscosity or stickiness to resin combination
System.In this case, resin combination is used under no any solvent.
As for (methyl) acyclic compound adjusted for viscosity, such as Jia base Bing Xi Suan Benzyl ester, phenyl can be used
Maleimide, cyclohexyl methacrylate, acrylic acid tetrahydrofuran ester, tetrahydrofurfuryl methacrylate, methacrylic acid
Tetrahydropyrans ester, N- pyrrole pyridine ketone, isobornyl methacrylate, ethylhexyl acrylate, n-butyl acrylate, third
Olefin(e) acid ethyl ester, methyl acrylate, vinyl acrylate, 2- hydroxy acrylate, β-acryloxy propionic or acrylic acid.
Based on the silsesquioxane resin of 100 parts by weight, (methyl) acyclic compound for viscosity adjustment preferably with
The amount of 15 to 70 parts by weight exists.If (methyl) acyclic compound for viscosity adjustment is less than the lower limit defined above,
Then the viscosity of composition may be excessively high.Meanwhile if (methyl) acyclic compound for viscosity adjustment is more than to define above
The upper limit, then the physical property of substrate produced may deteriorate.
Organic solvent is not particularly limited, as long as it can dissolve polymer.Organic solvent can be general
Any organic solvent used in photopolymerizable composition, the example include acetic acid esters system, ether system, ethylene glycol system, ketone system, alcohol system,
And carbonic ester system organic solvent.For example, organic solvent can be selected from by ethyl Sai Lusu, butyl Sai Lusu, ethyl carbitol, fourth
Base carbitol, ethylcarbitol acetate, acetate of butyl carbitol, ethylene glycol, cyclohexanone, cyclopentanone, 3- ethoxy-propionic acid,
Group composed by DMAC N,N' dimethyl acetamide, N- methylpyrrole pyridine ketone, N- methyl caprolactam and above-mentioned mixture.
Based on the composition of 100 parts by weight, organic solvent can be with 0 to 95 parts by weight, the amount of preferably 10 to 90 parts by weight
In the presence of.If the content of solvent is more than the upper limit defined above, then possibly can not obtain with the thin of required thickness after coating
Film.
(F) additive
One embodiment according to the present invention, additive are selected from by antioxidant, light stabilizer and interfacial agent institute
The group of composition.
Interfacial agent has the function of improving coating on substrate, the coating homogeneity of composition and from composition
The ingredient of the middle ability for removing spot.Interfacial agent can selected from by fluorination interfacial agent, silicon substrate interfacial agent, it is non-from
Group composed by sub-interface activating agent and above-mentioned mixture.
The representative example of antioxidant suitable for the composition include Irganox 1010, Irganox 1035,
Irganox 1076 and Irganox 1222 (Ciba-Geigy, Japan).The example of suitable light stabilizer includes: Tinuvin
292, Tinuvin 144 and Tinuvin 622LD (Ciba-Geigy, Japan)；And sanol LS-770, sanol LS-
765, sanol LS-292 and sanol LS-744 (Sankyo, Japan).
Based on the silsesquioxane resin of 100 parts by weight, the dosage of additive is usually 0.001 to 2 parts by weight, preferably
0.01 to 1 parts by weight.The amount of additive can according to user selection and change, as long as object needed for Photosensitve resin composition
Rationality matter does not change.
In some embodiments, other than ingredient (A) to (F), resin combination can optionally further comprise (G)
Inorganic particle.Surface hardness and wearability of the inorganic particle to improve resin combination.For example, inorganic particle can be dioxy
Silicon carbide particle, titanium dioxide granule, zirconia particles, antimony oxide particle or Zinc oxide particles.
Based on the silsesquioxane resin of 100 parts by weight, the dosage of inorganic particle can be 0.1 to 15 parts by weight.If
The amount of inorganic particle is less than the lower limit defined above, then it could not be expected that the hardness of resin combination is fully enhanced.Meanwhile it is false
The amount for making inorganic particle is more than the upper limit that defines above, then the transmissivity that may cause resin combination is low or mist degree is high.
There is high-transmission rate and pliability for the resin combination of transparent plastic substrate according to the present invention, and show
Good heat resistance, scratch resistance and impact resistance.Due to these advantages, resin combination of the invention can be used for manufacturing with excellent
The substrate of different physical property.
One embodiment according to the present invention, resin combination can be used for producing thick plastic basis material.It can not limit
Thick substrate is formed under system using any technology known in technical field, and the example includes spin coating, dip-coating, roller
It applies, net painting, flow coat, screen painting and droplet casting.In subsequent UV curing schedule, solvent is under vacuum by using infrared light
Irradiate or pass through heating evaporation.Then, composition is made to be exposed selectively to excimer laser, extreme ultraviolet light, ultraviolet light, visible
Light, electron beam, X-ray, g line (wavelength 436nm), i line (wavelength 365nm), h line (wavelength 405nm) or above-mentioned mixed light.Example
Such as, contact, neighbouring or projection exposure be can use.Resin combination can be by being heating and curing.In such a case, it is possible to logical
It crosses and resin combination is heated to 200 DEG C or less, preferably 100 to 150 DEG C effectively to obtain with high-intensitive cured film.Heating
It is preferred that carrying out 5 minutes to 2 hours, more preferably carry out 10 minutes to 1 hour.
Further embodiment of the present invention provides the overlay formed using the resin combination.Overlay
Thickness can select in 5 μm to 5,000 μm of range, depending on expected purpose.
Another embodiment of the present invention provides the substrates including the overlay.The substrate can be used for semiconductor group
Part, liquid crystal display (LCD) device, Organic Light Emitting Diode (OLED) component, solar battery apparatus, flexible display device or touching
Screen apparatus is controlled, or can be applied to through nano-imprint lithography art manufacturing device.
The present invention will be explained in greater detail referring to following instance.It is for illustrative purposes for providing these examples, and
The scope of the present invention is not limited to this.
Example
1. the synthesis of oligomeric silsesquioxane fluoropolymer resin
[synthesis example 1]
The fluoropolymer resin indicated by following procedure preparation formula 2.
Potassium carbonate (1g) is dissolved in solvents tetrahydrofurane (200mL) under stirring at room temperature.To this during 2 hours
Methyltrimethoxysilane (0.3 mole), (bicyclic [2.2.1] the hept-2-ene" base of 5-) triethoxysilane is slowly added dropwise in solution
(0.3 mole) and methacrylic acid 3- (triethoxy silicon substrate) propyl ester (0.4 mole).After being added dropwise to complete, react 12 hours.
Removal potassium carbonate is filtered by micro-filter.Tetrahydrofuran is evaporated off under reduced pressure, obtains the subject copolymers of formula 2, is a liquid.
The molecular weight and polydispersity index of product are measured by gpc analysis on the basis of polystyrene.It was found that polymer
The weight average molecular weight of resin is 24,000, polydispersity index 2.8.
[synthesis example 2]
The fluoropolymer resin indicated by formula 3 is prepared in a manner of identical with synthesis example 1, the difference is that only using front three
Oxygroup (3- (ethylene oxide -2- ylmethoxy) propyl) silane (0.4 mole) substituent methyl acrylic acid 3- (triethoxy silicon substrate)
Propyl ester.
The molecular weight and polydispersity index of product are measured by gpc analysis on the basis of polystyrene.It was found that polymer
The weight average molecular weight of resin is 28,000, polydispersity index 3.2.
Example 1-10
Photocuring and heat-curing composition are prepared using the fluoropolymer resin of synthesis example 1-2.Specifically, by 40 parts by weight
The fluoropolymer resin of synthesis example 1 or 2, the Irgacure 184 of 2 parts by weight or TPM-P07 (TAKOMA technical concern Co., Ltd)
As photopolymerization initiator or the Jeffamine D230 of 5 parts by weight as amido thermal polymerization initiator, two seasons of 15 parts by weight
Penta 4 alcohol radicals (dipentahexaerythritol-based) acrylic acid polyfunctional compound (the chemical stock of M500, MIWON spy
Part Co., Ltd), five vinyl pentamethyl cyclopentasiloxanes (Gelest) of 10 parts by weight or modified epoxy (KDSF180,
Kukdo chemistry limited liability company) as toughener, dimethylbenzene as organic solvent and the bonding reinforcing agent (KBM of 2 parts by weight
403, SHIN-ETSU) it mixes.After being stirred at room temperature 4 hours, by mixture by 10 μm of filter filterings to obtain
Solid content is adjusted to 35% composition.The ingredient of composition (example 1 to 10) and its content are listed in table 1.
Table 1
[comparative example 1]
Use polymethyl methacrylate (PMMA) piece of 800 μ m-thicks as the material of transparent plastic substrate.
[physical property assessment]
The every kind of Photocurable composition prepared in example 1 to 8 is applied on spin coater with 600-1000rpm and carries out 15
Second, and it is 100 seconds dry on 90 DEG C of hot plate.Dry composition is set to be exposed to the metalized lamp for using UVA wavelength as light source,
To form the film of 100 μ m-thicks.The every kind of heat-curing composition prepared in spin coating example 9 and 10 and the drying on 90 DEG C of hot plate
100 seconds, and solidify 30 minutes films to form 100 μ m-thicks at 150 DEG C.Following parameter is assessed to film.
(1) pencil hardness
According to KS D6711 test method, using Mitsubishi pencil with 45 ° of pencil lead angle amount under the load of 1kg
Survey the hardness of each film.According to most as low as the sequence of maximum hardness use pencil.The hardness of coating surface is defined as visually seeing
Observe the grade before scratch or impression formation.The hardness level of pencil is mentioned with 2B < B < HB < H < 2H < 3H < 4H < 5H < 6H sequence
It is high.
(2) wearability
Erasing rubber is attached to coating surface under the load of 1kg, and with 69 beats/min of rate reciprocal 2,000 time.It sees
It examines and whether is atomized on surface.
(3) scratch resistance
By steel wool (#0000) in 500g/cm2Load under moved back and forth on coating surface with the rate of 69mm/sec
After 100 times, observe whether form scratch on surface.
(4) chemical resistance
The chemical resistance of each film is assessed according to 2792 test method of ASTM D.Firstly, by 5% hydrochloric acid, 5% sulfuric acid,
MEK, acetone and DMF are dripped on coating surface.After standing 4 hours at room temperature, the variation on surface is observed.
(5) antiscale
The antiscale of each film is assessed according to 3332 test method of KS M.Firstly, by coffee, milk, soybean juice, pickles
Juice, cola, tomato sauce, 5% acetic acid, 5% ammonium hydroxide etc. drip on coating surface.It is washed with water after standing 24 hours at room temperature
Surface.Whether observation surface is contaminated.
(6) transmissivity
The transmissivity of each film of UV spectrometer measurement is used at 400-800nm and is averaged.
(7) crackle
The state of each film is observed after photocuring and heat cure, visually to judge whether form crackle on film.
Result is recorded in table 2.
Table 2
From the results shown in Table 2, compared with general plastic basis material (PMMA), the transparent modeling of example 1,3,5,7 and 9
Material base material film shows excellent physical property.
Claims (8)
1. a kind of resin combination for transparent plastic substrate, includes:
(A) silsesquioxane resin indicated by formula 1:
Wherein R1、R2And R3The C for respectively standing alone as singly-bound, being substituted or being unsubstituted1-C6Alkyl is stretched, is substituted or is unsubstituted
- O-CxH2x, the integer that wherein x is 1 to 6 or the-C that is substituted or is unsubstitutedyH2y-O-CzH2z, wherein y and z is whole
Number, and the integer that y+z is 2 to 12,
Each R1aAll stand alone as the C for being substituted or being unsubstituted1-C12Alkyl or the C for being substituted or being unsubstituted3-C18Cyclic hydrocarbon
Base,
Each R2aAll stand alone as C being substituted or be unsubstituted, with ethylenic linkage2-C12Alkyl, each R3aIt all stands alone as through taking
Generation or be unsubstituted containing C2-C10Cyclic ether group,
The integer that l is 2 to 500, and
M and n respectively stands alone as 0 to 500 integer, on condition that at least one in m and n is not 0；And
(B) photopolymerization initiator or thermal curing agents；
(C) there is the polyfunctional compound of vinylation unsaturated bond,
(D) toughener,
(E) (methyl) acyclic compound or organic solvent for viscosity adjustment,
And (F) at least one additive selected from antioxidant, light stabilizer and interfacial agent.
2. resin combination as described in claim 1, wherein in R1aIn, the C for being substituted or being unsubstituted1-C12Alkyl is
Methyl, ethyl, propyl, butyl, hexyl or octyl, the C for being substituted or being unsubstituted3-C18Cyclic hydrocarbon radical is naphthenic base, bicyclic alkane
Base, aryl or heteroaryl.
3. resin combination as described in claim 1, wherein R2aFor containing end 3- methylacryloyl, 3- acryloyl group,
The alkyl of vinyl or allyl.
4. resin combination as described in claim 1, wherein in R3aIn, what this was substituted or was unsubstituted contains C3-C12Cyclic ethers
Group is the alkyl containing terminal glycidyl group, 2- (3,4- epoxycyclohexyl) or oxetanes -3- base.
5. resin combination as described in claim 1, wherein the silsesquioxane resin has 2,000 to 100,000 weight
Measure average molecular weight.
6. resin combination as described in claim 1, wherein repetitive unit (I) in the silsesquioxane resin, (II) and
(III) ratio is respectively 1 to 90 mole of %, 0 to 30 mole of % and 0 to 30 mole of %.
7. a kind of overlay is to be formed and had at 5 μm using composition such as described in any one of claims 1 to 6
Thickness into 5,000 μ ms.
8. a kind of substrate includes overlay as claimed in claim 7.
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| KR20140048892 | 2014-04-23 | ||
| KR10-2014-0048892 | 2014-04-23 | ||
| PCT/KR2015/003990 WO2015163681A1 (en) | 2014-04-23 | 2015-04-21 | Resin composition for transparent plastic substrate |
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| KR (1) | KR101611935B1 (en) |
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| TWI606101B (en) | 2016-12-28 | 2017-11-21 | 財團法人工業技術研究院 | Coating composition and method of manufacturing the same |
| KR102412888B1 (en) | 2017-05-12 | 2022-06-28 | 삼성디스플레이 주식회사 | Hard coating composition, and window member having hard coating layer |
| KR101996262B1 (en) * | 2017-09-01 | 2019-10-01 | (주)휴넷플러스 | Barrier resin composition, method for uv curable barrier layer and electronic device |
| EP3785897B1 (en) | 2019-08-29 | 2021-12-29 | SHPP Global Technologies B.V. | Transparent, flexible, impact resistant, multilayer film comprising polycarbonate copolymers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101450977A (en) * | 2007-12-04 | 2009-06-10 | 佳能株式会社 | Optical material, optical element, and method for making optical element |
| KR20100131904A (en) * | 2009-06-08 | 2010-12-16 | 한국과학기술연구원 | Preparation method of organic-inorganic hybrid graft polysilsesquioxane and graft polysilsesquioxane prepared by the same |
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| KR100481911B1 (en) * | 2000-02-17 | 2005-04-13 | 주식회사 인터실리콘 | Polyorganosilsesquioxane and process for preparing the same |
| JP2005089705A (en) * | 2003-09-19 | 2005-04-07 | Jsr Corp | Sulfonic acid group-containing ladder silicone and composition |
| US20080221263A1 (en) * | 2006-08-31 | 2008-09-11 | Subbareddy Kanagasabapathy | Coating compositions for producing transparent super-hydrophobic surfaces |
| JP5075680B2 (en) * | 2007-03-28 | 2012-11-21 | リンテック株式会社 | Optical element sealing material and optical element sealing body |
| JP5281607B2 (en) * | 2010-03-18 | 2013-09-04 | 新日鉄住金化学株式会社 | Laminate film |
| KR101344872B1 (en) | 2011-10-17 | 2013-12-26 | 이근수 | polymer compositions, film obtained therefrom and manufacturing method thereof |
| JP2013129766A (en) | 2011-12-22 | 2013-07-04 | Nippon Steel & Sumikin Chemical Co Ltd | Glass fiber-composited resin substrate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101450977A (en) * | 2007-12-04 | 2009-06-10 | 佳能株式会社 | Optical material, optical element, and method for making optical element |
| KR20100131904A (en) * | 2009-06-08 | 2010-12-16 | 한국과학기술연구원 | Preparation method of organic-inorganic hybrid graft polysilsesquioxane and graft polysilsesquioxane prepared by the same |
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| KR20150122597A (en) | 2015-11-02 |
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| WO2015163681A1 (en) | 2015-10-29 |
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