TWI387615B - 壓克力奈米複合材料 - Google Patents
壓克力奈米複合材料 Download PDFInfo
- Publication number
- TWI387615B TWI387615B TW097142452A TW97142452A TWI387615B TW I387615 B TWI387615 B TW I387615B TW 097142452 A TW097142452 A TW 097142452A TW 97142452 A TW97142452 A TW 97142452A TW I387615 B TWI387615 B TW I387615B
- Authority
- TW
- Taiwan
- Prior art keywords
- acrylic
- acrylate
- inorganic
- monomer
- nano composite
- Prior art date
Links
- 239000002114 nanocomposite Substances 0.000 title claims description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims description 22
- 239000000463 material Substances 0.000 title claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 19
- 239000002105 nanoparticle Substances 0.000 claims description 19
- -1 acryl Chemical group 0.000 claims description 18
- 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 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007822 coupling agent Substances 0.000 claims description 13
- 239000002131 composite material Substances 0.000 claims description 9
- 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 claims description 8
- 125000002328 sterol group Chemical group 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 230000035699 permeability Effects 0.000 claims description 7
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims description 7
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical class CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 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 claims description 4
- 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 claims description 4
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 4
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 4
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 4
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 4
- DBJFSFSBHGPDPG-UHFFFAOYSA-N C(C(=C)C)(=O)OCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound C(C(=C)C)(=O)OCCCC(C(OC)(OC)OC)CCCCCCCC DBJFSFSBHGPDPG-UHFFFAOYSA-N 0.000 claims description 4
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 claims description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 4
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 3
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 3
- 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 claims description 3
- 239000000084 colloidal system Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 2
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- FGSFVBRPCKXYDI-UHFFFAOYSA-N 2-triethoxysilylethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C(C)=C FGSFVBRPCKXYDI-UHFFFAOYSA-N 0.000 claims description 2
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 claims description 2
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 claims description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910005793 GeO 2 Inorganic materials 0.000 claims description 2
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000006612 decyloxy group Chemical group 0.000 claims description 2
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 3
- XTVNGRMJOGNDOG-UHFFFAOYSA-N 1-trimethoxysilylpropan-2-yl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CC(C)OC(=O)C(C)=C XTVNGRMJOGNDOG-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- BUJVPKZRXOTBGA-UHFFFAOYSA-N 2-trimethoxysilylethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C=C BUJVPKZRXOTBGA-UHFFFAOYSA-N 0.000 claims 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 125000005498 phthalate group Chemical class 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- UNUDTFPPTQWKMU-UHFFFAOYSA-N 6-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)-N-phenylcyclohexa-2,4-dien-1-amine Chemical compound FC(C(C(F)(F)F)=C1C(C=CC=C1)NC1=CC=CC=C1)(F)F UNUDTFPPTQWKMU-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 108010039918 Polylysine Proteins 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 239000012784 inorganic fiber Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000656 polylysine Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- WJVNLGUHAAAGAR-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CC(O)COC(C)CO WJVNLGUHAAAGAR-UHFFFAOYSA-N 0.000 description 1
- PSLRXNFNXYNXEK-UHFFFAOYSA-N 2-triethoxysilylethyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C=C PSLRXNFNXYNXEK-UHFFFAOYSA-N 0.000 description 1
- RDCTZTAAYLXPDJ-UHFFFAOYSA-N 2-trimethoxysilylethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C(C)=C RDCTZTAAYLXPDJ-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
- ROGHJYKAJMKLRT-UHFFFAOYSA-N C(C(=C)C)(=O)OCCOCCOCCOCCOC(C(=C)C)=O.C(C(=C)C)(=O)OCCOCCOCCOCCOC(C(=C)C)=O Chemical compound C(C(=C)C)(=O)OCCOCCOCCOCCOC(C(=C)C)=O.C(C(=C)C)(=O)OCCOCCOCCOCCOC(C(=C)C)=O ROGHJYKAJMKLRT-UHFFFAOYSA-N 0.000 description 1
- CAPASJMRWSXMKM-UHFFFAOYSA-N C(C=C)(=O)OC(C)COC(C)COC(C=C)=O.CC(COC(C)COC(C)CO)O Chemical compound C(C=C)(=O)OC(C)COC(C)COC(C=C)=O.CC(COC(C)COC(C)CO)O CAPASJMRWSXMKM-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Dental Preparations (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
本發明係關於一種壓克力奈米複合材料,特別係關於一種用於光電元件封裝、牙科填補與光波導之壓克力奈米複合材料。
於高分子材料中引入無機填充材料用以增加材料之機械強度與熱穩定性已廣泛地被運用,其中,利用矽烷偶合劑改質無機物之表面更添其應用性,矽烷對於一般性結構材料如強化塑膠中的無機纖維,若將上述無機纖維預浸過矽烷溶液後再與塑膠接合,其介面作用力會增加,且能提升材料之整體強度;而矽烷偶合劑對於電子材料如矽晶圓類之無機基材表面改質,矽烷偶合劑能改變其化學反應性及親疏水性質以便符合所需,再者,矽烷偶合劑能加強複合材料中之有機基質與無機粒子間的作用力以獲得較強之機械性質,並改善其介面性質。
另一方面,氟原子具有較小的原子半徑與最大的陰電性,因此相對於其它鹵素原子,它可與碳原子形成較安定的鍵結。而利用這些特殊性質,近年來開發了許多高性能的含氟芳香族聚合物,尤其是於聚醯亞胺中導入氟原子後,可以有效地增加其溶解性、加工性與透光性,並能降低其介電常數與吸濕性,因此在電機、電子及光電材料產業中逐漸受到重視。
因此,根據以上所述,開發出結合上述優勢之材料係產業界亟欲發展之重點。
鑒於上述發明背景中,為了符合產業上之要求,本發明提供一種壓克力奈米複合材料。
本發明之特徵在於提供一種壓克力奈米複合材料,其係能應用於光電元件封裝材料、牙科填補複合材料與光波導,上述壓克力奈米複合材料包含一種無機奈米粒子、一種具有至少二個丙烯酯基團之丙烯酸酯單體、一種醯酯壓克力寡聚物與一光起始劑。其經光聚合反應後所形成之有機/無機交聯網絡結構的吸水率(%)可以小至0.01~1.00之間;而滲水率(g/m2
‧hr)則能低至0.01~2.00之間。
根據以上所述之特徵,本發明揭示了一種壓克力奈米複合材料,其具有甚低之吸水率(%)與滲水率(g/m2
‧hr),並且具有超過90%之透光度,因此本材料係尤適合作為光電元件之封裝材料。
本發明在此所探討的方向為一種壓克力奈米複合材料。為了能徹底地瞭解本發明,將提出詳盡的描述說明。顯然地,本發明的施行並未限定於該領域之技藝者所熟習的特殊細節。另一方面,眾所周知的組成或步驟並未描述於細節中,以避免造成本發明不必要之限制。本發明的較佳實施例會詳細描述如下,然而除了這些詳細描述之外,本發明還可以廣泛地施行在其他的實施例中,且本發明的範圍不受限定,其以之後的專利範圍為準。
本發明之一實施例係揭露一種壓克力奈米複合材料,上述壓克力奈米複合材料包含一種無機奈米粒子、一種具有至少二個丙烯酯基團之丙烯酸酯單體、一種醯酯壓克力寡聚物與一光起始劑,上述壓克力奈米複合材料藉由一光聚合反應(Photopolymerisable Reaction)產生交聯作用,藉以形成一有機/無機交聯網絡結構,其中,上述無機奈米粒子之粒徑範圍為10nm~100nm,並且其於壓克力奈米複合材料中之含量為10%至80%。
其中,上述無機奈米粒子係衍生自一無機奈米膠體溶液與一偶合劑,其中,上述無機奈米膠體溶液包含一表面具有一第一矽醇官能基之第一無機奈米粒子;再者,上述偶合劑之一端包含一種丙烯酸酯基團,而另一端包含一種矽氧烷基,當上述偶合劑經水解反應後,上述矽氧烷基形成一第二矽醇官能基,並且上述第二矽醇官能基與上述第一矽醇官能基產生鍵結,使得上述無機奈米粒子表面具有可反應性之上述丙烯酸酯基團,此外,上述無機奈米粒子係選自下列族群之一者:SiO2
、ZrO2
、TiO2
、Al2
O3
、ZnO2
、Fe2
O3
、SnO2
、Y2
O3
、GeO2
、Ni2
O3
與HfO2
,其中,較佳者:SiO2
、ZrO2
、TiO2
與Al2
O3
。其次,上述偶合劑係獨立選自下列族群之一者:3-(甲基丙烯醯氧)丙基三甲氧基矽烷(3-methacryloxypropyl trimethoxysilane;MPS)、3-(甲基丙烯醯氧)丙基二甲氧基矽烷3-methacryloxypropylmethyl dimethoxysilane、3-烯丙氧丙基三甲氧基矽(3-acryloxypropyl trimethoxysilane)、2-甲基丙烯酸醯氧丙基三甲氧基矽烷(2-methacryloxyethyl trimethoxysilane)、2-烯丙氧丙基三甲氧基矽(2-acryloxyethyl trimethoxysilane)、3-甲基丙烯酸醯氧丙基三乙氧基矽烷(3-methacryloxypropyl triethoxysilane)、3-烯丙氧丙基三乙氧基矽(3-acryloxypropyl triethoxysilane)、2-甲基丙烯酸醯氧丙基三乙氧基矽烷(2-methacryloxyethyl triethoxysilane)與2-烯丙氧丙基三乙氧基矽(2-acryloxyethyl triethoxysilane),其中,較佳者:3-(甲基丙烯醯氧)丙基三甲氧基矽烷、3-烯丙氧丙基三甲氧基矽與3-烯丙氧丙基三乙氧基矽。
再者,上述醯酯壓克力寡聚物包含一衍生自一種二胺單體與一種二酐單體的醯酯寡聚物之第一結構與一種衍生自一種丙烯酸羥酯單體之第二結構,其中,上述二胺單體與二酐單體經反應形成一聚醯亞胺,上述聚醯亞胺再與丙烯酸羥酯單體反應形成該醯酯壓克力寡聚物。另外,上述丙烯酸羥酯單體係選自下列族群之一者:乙氧化甲基丙烯酸羥乙酯(ethoxylated hydroxyethyl methacrylate;EOHEMA)、丙烯酸4-羥丁酯(4-hydroxybutyl acrylate;4HBA)、甲基丙烯酸-2-羥乙酯(2-hydroxyethyl methacrylate;HEMA)、甲基丙烯酸-2-羥丙酯(2-hydroxypropyl methacrylate;HPMA),較佳者係甲基丙烯酸-2-羥乙酯。
此外,上述壓克力奈米複合材料,更包含至少一種具丙烯酸酯基之化合物,上述之具丙烯酸酯基之化合物係為一單體或一寡聚物,其係選自下列族群之一者:1,4丁二醇二丙烯酸酯(1,4-butanediol diacrylate;BDDA)、1,4-丁二醇二甲基丙烯酸酯(1,4-butanediol dimethacrylate;BDDMA)、1,3-丁二醇二丙烯酸酯(1,3-butylene glycol diacrylate;BGDA)、1,3-丁二醇二甲基丙烯酸(1,3-butylene glycol dimethacrylate;BGDMA)、二乙二醇二丙烯酸酯(diethylene glycol diacrylate;DEGDA)、二乙二醇二甲基丙烯酸酯(diethylene glycol dimethacrylate;DEGDMA)、二丙二醇二丙烯酸(dipropylene glycol diacrylate;DPGDA)、乙二醇二甲基丙烯酸(ethylene glycol dimethacrylate;EGDMA)、乙氧基化雙酚A丙烯酸酯(ethoxylated bisphenol A diacrylate;EOBDA)、1,6-己二醇二丙烯酸酯(1,6-hexanediol diacrylate;HDDA)、1,6-己二醇二丙烯酸酯(1,6-hexanediol dimethacrylate;HDDMA)、新戊二醇雙丙烯酸酯(neopentyl glycol diacrylate;NPGDA)、新戊二醇二甲基丙烯酸酯(neopentyl glycol dimethacrylate;NPGDMA)、四乙二醇雙丙烯酸酯(tetraethylene glycol diacrylate;TEGDA)、四乙二醇雙甲基丙烯酸酯(tetraethylene glycol dimethacrylate;TEGDMA)、三乙二醇雙丙烯酸酯(triethylene glycol diacrylate;3EGDA)、二甲基丙烯酸三甘醇酯(triethylene glycol dimethacrylate;3EGDMA)與三丙二醇二丙烯酸酯(tripropylene glycol diacrylate;TPGDA),其中,較佳者:二乙二醇二丙烯酸酯、二丙二醇二丙烯酸、乙氧基化雙酚A丙烯酸酯、四乙二醇雙丙烯酸酯與三丙二醇二丙烯酸酯。
另一方面,上述光起始劑係選自下列族群之一者:2,2-二甲氧基-2-苯基-乙苯酮(2,2-dimethoxy-2-phenyl-acetophenone;Irgacure 651)、1-羥基環己基苯基甲酮(1-hydroxy cyclohexyl-phenyl-ketone;Irgacure 184)(2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone;Irgacure 2959)、(2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butanone;Irgacure 369)與(2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanone;Irgcure 907),其中,佳者:2,2-二甲氧基-2-苯基-乙苯酮與1-羥基環己基苯基甲酮。)
於本實施例之較佳範例中,上述醯酯壓克力寡聚物之一般式如下所示:
其中,n≧1,X係選自下列族群之一者:
,其中,較佳者為。
Y係選自下列族群之一者:
,其中,較佳者為
,此外,Z為丙烯酸羥酯單體。
上述壓克力奈米複合材料係能應用於光電元件封裝材料、牙科填補複合材料與光波導,其經光聚合反應後所形成之有機/無機交聯網絡結構的吸水率(%)為0.01至1.00之間;而滲水率(g/m2
‧hr)為0.01至2.00之間。
(i)
無機奈米粒子之表面改質
首先將20mL矽溶膠溶液(MA-STM)與20mL甲醇混合10分鐘,隨後加入2mL偶合劑(3-(甲基丙烯醯氧)丙基三甲氧基矽烷;MPS),於50℃下環境下反應24小時以形成具有可反應性之丙烯酸酯基團之無機奈米粒子。
(ii)光敏醯酯壓克力寡聚物(PSI)之合成
於氮氣氛與室溫環境下進行反應,將六氟二酐(6FDA,4.09g,2.05mol)與六氟異亞丙基二苯胺(6FpDA,1.5g,1mol)分別溶解於23mL與11mL之二甲基乙胺(DMAc),接著將上述六氟二酐溶液與六氟異亞丙基二苯胺溶液混合以形成聚醯胺酸,以氮氣吹掃(N2
purge)後將乙酸酐(1.69mL)與砒啶(1.83mL)加入上述聚醯胺酸中形成一混合溶液,其次,將上述混合溶液加熱至90℃並攪拌7小時以形成聚亞醯胺,待上述聚亞醯胺溶液冷卻後以離心機除去未反應之前驅物,接著,將聚亞醯胺沉澱以150℃真空下乾燥24小時以形成去二酐基團之亞胺粉末,再者,將亞胺粉末(4g,1mol)再溶解於二甲基乙胺(DMAc)中,並與甲基丙烯酸-2-羥乙酯(HEMA,2.20g,5mol)及對苯二酚(0.029g,0.073mol)於大氣壓75℃環境下反應24小時,最後,除去未反應之前驅物後獲得上述之光敏醯酯壓克力寡聚物。
(iii)壓克力奈米複合溶液之製備
將具有可反應性之丙烯酸酯基團之上述無機奈米粒子、四乙二醇雙丙烯酸酯(TEGDA)與乙氧基化雙酚A丙烯酸酯(EOBDA)混合物、光敏醯酯壓克力寡聚物(PSI)與光起始劑置於不透光之反應瓶中,並且於室溫下攪拌1小時,最後於真空下除去溶劑以得到一無溶劑之壓克力奈米複合溶液。
(iv)壓克力奈米複合材料之光聚合
將無溶劑之壓克力奈米複合溶液澆鑄於一聚對苯二甲酸乙二酯(PET)模具上,接著於氮氣室(N2
chamber)中以紫外光(365nm,1.86mW/cm2
)硬化2分鐘以形成有機/無機交聯網絡結構。
此外,壓克力奈米複合材料中之各組成重量比例如下表一所示,其中,壓克力奈米複合材料之4wt%為光起始劑。
其中,上述交聯網絡結構透光度均超過90%,因而適合作為光電元件之封裝材料,如第一圖所示。
再者,隨著壓克力奈米複合材料中之無機奈米粒子組成增加,其機械強度隨之提升,其硬度與楊氏係數(Young’s modulus)如第二圖所示。又,上述無機奈米粒子於交聯網絡結構中呈現出緊密堆積貌,如第三圖所示,其中,(a)FS20,(b)FS40,(c)FS60,(d)NPS20,(e)NPS40,(f)NPS60。此外,添加無機填充物(無機奈米粒子)於高分子材料中能提高其耐熱程度,其裂解溫度與熱膨脹係數如第四圖所示。
另一方面,上述有機/無機交聯網絡結構之吸水率(%)與滲水率(g/m2
‧hr)如第五圖所示,其中,含有PSI組成之壓克力奈米複合材料(NPS)之吸水率(%)與滲水率(g/m2
‧hr)均甚低於無添加PSI之壓克力奈米複合材料(FS)。
顯然地,依照上面實施例中的描述,本發明可能有許多的修正與差異。因此需要在其附加的權利要求項之範圍內加以理解,除了上述詳細的描述外,本發明還可以廣泛地在其他的實施例中施行。上述僅為本發明之較佳實施例而已,並非用以限定本發明之申請專利範圍;凡其它未脫離本發明所揭示之精神下所完成的等效改變或修飾,均應包含在下述申請專利範圍內。
第一圖為具各比例組成之有機/無機交聯網絡結構之透光度圖譜,其中,(a)FS,(b)NPS;
第二圖為有機/無機交聯網絡結構之硬度與楊氏係數(Young’s modulus)圖譜;
第三圖為有機/無機交聯網絡結構之穿透式電子顯微鏡照片;
第四圖為有機/無機交聯網絡結構之裂解溫度與熱膨脹係數圖譜;
第五圖為有機/無機交聯網絡結構之吸水率(%)與滲水率(g/m2
‧hr)圖譜。
Claims (13)
- 一種壓克力奈米複合材料,該壓克力奈米複合材料包含:一種無機奈米粒子,其係衍生自一無機奈米膠體溶液與一偶合劑,其中,該無機奈米膠體溶液包含一表面具有一第一矽醇官能基之第一無機奈米粒子;該偶合劑之一端包含一種丙烯酸酯基團,而另一端包含一種矽氧烷基,其中,該偶合劑經水解反應後,該矽氧烷基形成一第二矽醇官能基,該第二矽醇官能基與該第一矽醇官能基產生鍵結,使得該無機奈米粒子表面具有可反應性之該丙烯酸酯基團;一種丙烯酸酯單體,其中,該單體具有至少二個丙烯酯基;一種醯酯壓克力寡聚物,該醯酯壓克力寡聚物包含:一衍生自一種二胺單體與一種二酐單體的醯酯寡聚物之第一結構與一種衍生自一種丙烯酸羥酯單體之第二結構,其中,該二胺單體與該二酐單體經反應形成一聚醯亞胺,該聚醯亞胺再與該丙烯酸羥酯單體反應形成該醯酯壓克力寡聚物;以及一光起始劑,其中,該壓克力奈米複合材料藉由一光聚合反應(Photopolymerisable Reaction)產生交聯作用,藉以形成一有機/無機交聯網絡結構。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該無機奈米粒子於該壓克力奈米複合材料中之含量為10%至80%。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該奈米粒 子之粒徑範圍係10nm~100 nm之間。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,其中,該無機奈米粒子係選自下列族群之一者:SiO2 、ZrO2 、TiO2 、Al2 O3 、ZnO2 、Fe2 O3 、SnO2 、Y2 O3 、GeO2 、Ni2 O3 與HfO2 。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,其中,該偶合劑係獨立選自下列族群之一者:3-(甲基丙烯醯氧)丙基三甲氧基矽烷(3-methacryloxypropyl trimethoxysilane;MPS)、3-(甲基丙烯醯氧)丙基二甲氧基矽烷3-methacryloxypropylmethyl dimethoxysilane、3-烯丙氧丙基三甲氧基矽(3-acryloxypropyl trimethoxysilane)、2-甲基丙烯酸醯氧丙基三甲氧基矽烷(2-methacryloxyethyl trimethoxysilane)、2-烯丙氧丙基三甲氧基矽(2-acryloxyethyl trimethoxysilane)、3-甲基丙烯酸醯氧丙基三乙氧基矽烷(3-methacryloxypropyl triethoxysilane)、3-烯丙氧丙基三乙氧基矽(3-acryloxypropyl triethoxysilane)、2-甲基丙烯酸醯氧丙基三乙氧基矽烷(2-methacryloxyethyl triethoxysilane)與2-烯丙氧丙基三乙氧基矽(2-acryloxyethyl triethoxysilane)。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,其中,更包含至少一種具丙烯酸酯基之化合物,該具丙烯酸酯基之化合物係為一單體或一寡聚物。
- 如申請專利範圍第6項所述之壓克力奈米複合材料,該具丙烯酸酯基之化合物係選自下列族群之一者:1,4丁二醇二丙烯酸酯(1,4-butanediol diacrylate;BDDA)、1,4-丁二醇二甲基丙烯酸酯(1,4-butanediol dimethacrylate;BDDMA)、1,3-丁二醇二丙烯酸酯(1,3-butylene glycol diacrylate;BGDA)、1,3-丁二醇二甲基丙烯酸(1,3-butylene glycol dimethacrylate;BGDMA)、二乙二醇二丙烯酸酯(diethylene glycol diacrylate;DEGDA)、二乙二醇二甲基丙烯酸酯(diethylene glycol dimethacrylate;DEGDMA)、二丙二醇二丙烯酸(dipropylene glycol diacrylate;DPGDA)、乙二醇二甲基丙烯酸(ethylene glycol dimethacrylate;EGDMA)、乙氧基化雙酚A丙烯酸酯(ethoxylated bisphenol A diacrylate;EOBDA)、1,6-己二醇二丙烯酸酯(1,6-hexanediol diacrylate;HDDA)、1,6-己二醇二甲基丙烯酸酯(1,6-hexanediol dimethacrylate;HDDMA)、新戊二醇雙丙烯酸酯(neopentyl glycol diacrylate;NPGDA)、新戊二醇二甲基丙烯酸酯(neopentyl glycol dimethacrylate;NPGDMA)、四乙二醇雙丙烯酸酯(tetraethylene glycol diacrylate;TEGDA)、四乙二醇雙甲基丙烯酸酯(tetraethylene glycol dimethacrylate;TEGDMA)、三乙二醇雙丙烯酸酯(triethylene glycol diacrylate;3EGDA)、二甲基丙烯酸三甘醇酯(triethylene glycol dimethacrylate;3EGDMA)與三丙二醇二丙烯酸酯(tripropylene glycol diacrylate;TPGDA)。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該丙烯酸羥酯單體係選自下列族群之一者:乙氧化甲基丙烯酸羥乙酯(ethoxylated hydroxyethyl methacrylate;EOHEMA)、丙烯酸4-羥丁酯(4-hydroxybutyl acrylate;4HBA)、甲基丙烯酸-2-羥乙酯(2-hydroxyethyl methacrylate;HEMA)、甲基丙烯酸-2-羥丙酯(2-hydroxypropyl methacrylate;HPMA)。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,其中,該醯酯壓克力寡聚物之一般式如下所示:
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該光起始劑係選自下列族群之一者:2,2-二甲氧基-2-苯基-乙苯酮(2,2-dimethoxy-2-phenyl-acetophenone;Irgacure 651)、1-羥基環己基苯基甲酮(1-hydroxy cyclohexyl-phenyl-ketone;Irgacure 184)、(2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone;Irgacure 2959)、(2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butanone;Irgacure 369)與(2-methyl-1-[4-(methylthio)phenyl]-2-(4-morpholinyl)-1-propanone;Irgcure 907)。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該壓克力奈米複合材料具有下列之應用:光電元件封裝材料、牙科填補複合材料與光波導。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該有機/無機交聯網絡結構之吸水率(%)為0.01至1.00之間。
- 如申請專利範圍第1項所述之壓克力奈米複合材料,該有機/無機交聯網絡結構之滲水率(g/m2 .hr)為0.01至2.00之間。
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TW097142452A TWI387615B (zh) | 2008-11-04 | 2008-11-04 | 壓克力奈米複合材料 |
US12/544,390 US8133931B2 (en) | 2008-11-04 | 2009-08-20 | Acrylate nanocomposite material |
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US5310862A (en) * | 1991-08-20 | 1994-05-10 | Toray Industries, Inc. | Photosensitive polyimide precursor compositions and process for preparing same |
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