JP6763139B2 - 無溶剤型シリコーン変性ポリイミド樹脂組成物 - Google Patents
無溶剤型シリコーン変性ポリイミド樹脂組成物 Download PDFInfo
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- JP6763139B2 JP6763139B2 JP2015252901A JP2015252901A JP6763139B2 JP 6763139 B2 JP6763139 B2 JP 6763139B2 JP 2015252901 A JP2015252901 A JP 2015252901A JP 2015252901 A JP2015252901 A JP 2015252901A JP 6763139 B2 JP6763139 B2 JP 6763139B2
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- polyimide resin
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- modified polyimide
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- 239000000203 mixture Substances 0.000 title claims description 96
- 229920001721 polyimide Polymers 0.000 title claims description 90
- 239000009719 polyimide resin Substances 0.000 title claims description 76
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 claims description 131
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 19
- 239000000853 adhesive Substances 0.000 claims description 18
- 230000001070 adhesive effect Effects 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- 238000002834 transmittance Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 15
- 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 14
- 229910021485 fumed silica Inorganic materials 0.000 claims description 14
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229920001296 polysiloxane Polymers 0.000 claims description 14
- 150000004985 diamines Chemical class 0.000 claims description 13
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 12
- 239000011164 primary particle Substances 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000004984 aromatic diamines Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000000101 thioether group Chemical group 0.000 claims description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001174 sulfone group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000004642 Polyimide Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 229920005575 poly(amic acid) Polymers 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910002012 Aerosil® Inorganic materials 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000011049 filling Methods 0.000 description 6
- 125000005462 imide group Chemical group 0.000 description 6
- 230000009974 thixotropic effect Effects 0.000 description 6
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XNGKCOFXDHYSGR-UHFFFAOYSA-N perillene Chemical compound CC(C)=CCCC=1C=COC=1 XNGKCOFXDHYSGR-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007875 V-40 Substances 0.000 description 3
- AVTLBBWTUPQRAY-BUHFOSPRSA-N V-59 Substances CCC(C)(C#N)\N=N\C(C)(CC)C#N AVTLBBWTUPQRAY-BUHFOSPRSA-N 0.000 description 3
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 3
- 239000007874 V-70 Substances 0.000 description 3
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 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 3
- 239000000945 filler Substances 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000005401 siloxanyl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000000411 transmission spectrum Methods 0.000 description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- YMMLZUQDXYPNOG-UHFFFAOYSA-N 2-methylpentan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)CCCCCC(C)(C)C YMMLZUQDXYPNOG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- YOEYNURYLFDCEV-UHFFFAOYSA-N tert-butyl hydroxy carbonate Chemical compound CC(C)(C)OC(=O)OO YOEYNURYLFDCEV-UHFFFAOYSA-N 0.000 description 1
- FFIUNPRXUCRYFU-UHFFFAOYSA-N tert-butyl pentaneperoxoate Chemical compound CCCCC(=O)OOC(C)(C)C FFIUNPRXUCRYFU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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Description
〔1〕
(A)下記式(2)の両末端にそれぞれアミノ基が結合したジアミノ変性シリコーンと、不飽和結合がカルボニル基に共役していないテトラカルボン酸二無水物と、脂肪族ジアミン又は芳香族ジアミンとの反応物から得られた、下記式(1)で表されるシリコーン変性ポリイミド樹脂:100質量部、
Ee−Ff−Gg (1)
(式(1)中、FにE又はGの各繰り返し単位がランダムに結合しており、Eは式(2)に示す2価の上記ジアミノ変性シリコーン由来の残基、Fは式(3)に示す上記テトラカルボン酸二無水物由来の残基、GはEを含まない上記ジアミン由来の2価の残基である。e、f、gはそれぞれ0を超える数であってf+e+g=1であり、上記ジアミノシロキサン、テトラカルボン酸二無水物及びジアミンの物質量から換算して求められるf/(e+g)のmol比が0.8〜1.2である。)
−Im−X−Im− (3)
(式(3)中、Imは環状イミド構造を端に含む環状の基であり、Xは単結合、酸素、硫黄、スルフィド基、スルホン基、カルボニル基、−NRN−(RNは炭素数1〜12の直鎖状、分岐状又は環状の1価炭化水素基)、−CRB 2−(RBは互いに独立に、水素原子、又は、置換又は非置換の炭素数1〜12の1価炭化水素基)、−RAr h−(RArは、炭素数6〜12の2価のアリーレン基、hは1〜6の整数)、アリーレン基から水素原子が1個又は2個脱離した3価又は4価の基、−RAr h(ORAr)i−(RArとhは前記と同定義であり、iは1〜5である。)、炭素数1〜12の直鎖状、分岐状又は環状のアルキレン基、該アルキレン基から水素原子が1個脱離した3価の基、アリーレンアルキレン基から選択される2〜4価の有機基である。)
(B)下記式(4')で表される(メタ)アクリル酸エステル化合物:100〜2,000質量部、
CH2=CR7C(=O)OR8 (4’)
(式中、R7は、炭素数1〜10の直鎖状又は分岐状のアルキル基であり、R8は、炭素数9〜16の直鎖状、分岐状又は環状のアルキル基である。)
(C)重合開始剤:(A)及び(B)成分の合計100質量部に対して0.1〜30質量部、
(D)疎水性フュームドシリカ:(A)及び(B)成分の合計100質量部に対して1〜50質量部
を含有してなり、25℃において流動性を有し、かつ溶剤を含まないことを特徴とする無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔2〕
Imが下記の基から選択されるものである〔1〕に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔3〕
(B)成分が(メタ)アクリル酸イソボルニル、(メタ)アクリル酸ノニル、(メタ)アクリル酸デシル、(メタ)アクリル酸ウンデシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸トリデシル、(メタ)アクリル酸テトラデシル、(メタ)アクリル酸ペンタデシル又は(メタ)アクリル酸ヘキサデシルである〔1〕又は〔2〕に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔4〕
(B)成分の配合量が(A)成分100質量部に対して100〜500質量部である〔1〕〜〔3〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔5〕
(C)成分が、熱分解性ラジカル開始剤、又は、放射線活性化開始剤である〔1〕〜〔4〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔6〕
(D)成分が、嵩密度が1g/mLより低く、平均一次粒子径が1〜100nmであり、BET比表面積が100〜300m2/gである疎水性フュームドシリカである〔1〕〜〔5〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔7〕
無溶剤型シリコーン変性ポリイミド樹脂組成物の25℃における粘度が3〜1,000Pa・sである〔1〕〜〔6〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔8〕
(H)成分としてエポキシ基含有アクリレートからなる接着強度改質用添加剤を含有する〔1〕〜〔7〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔9〕
(I)成分として(メタ)アクリル酸変性シリコーンからなるレベリング剤を含有する〔1〕〜〔8〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔10〕
(J)成分として染料を含有する〔1〕〜〔9〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
〔11〕
〔1〕〜〔10〕のいずれかに記載の組成物からなる接着剤。
〔12〕
〔1〕〜〔10〕のいずれかに記載の組成物からなるコーティング剤。
〔13〕
〔1〕〜〔10〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物を紫外線及び/又は可視光で硬化させた皮膜の貯蔵弾性率が1MPa以上500MPa以下であるシリコーン変性ポリイミド樹脂硬化物。
〔14〕
〔1〕〜〔9〕のいずれかに記載の無溶剤型シリコーン変性ポリイミド樹脂組成物を紫外線及び/又は可視光で硬化させた被膜が、可視光領域の波長で光透過率が80%以上であり、L*a*b*表色系でL*が80%以上、a*が−10%以上10%未満、b*が−10%以上10%未満であるシリコーン変性ポリイミド樹脂硬化物。
本発明のシリコーン変性ポリイミド含有組成物は、下記の(A)〜(D)成分を含有し、25℃において流動性を有し、かつ溶剤を含まないことを特徴とする無溶剤型シリコーン変性ポリイミド樹脂組成物である。
(A)シリコーン変性ポリイミド樹脂、
(B)重合性化合物、
(C)重合開始剤、
(D)疎水性フュームドシリカゲル
(A)成分のシリコーン変性ポリイミドは、本組成物の主剤(ベースポリマー)であって、該シリコーン変性ポリイミドとしては下記式(1)で示されるものを用いることができる。
Ee−Ff−Gg (1)
(式(1)中、Eは式(2)に示す2価のジアミノ変性シリコーン残基、Fは式(3)に示すテトラカルボン酸二無水物由来の残基、Gはジアミン由来の2価の残基である。
FにE又はGの各繰り返し単位がランダムに結合しており、f+e+g=100mol%であり、f/(e+g)のmol比が0.8〜1.2、特に0.95〜1.05である。)
(式(3)中、Imは環状イミド構造を端に含む環状の基であり、Xは単結合(2つのImを単結合にて連結)、酸素、硫黄、スルフィド基、スルホン基、カルボニル基、−NRN−(RNは炭素数1〜12の直鎖状、分岐状又は環状の1価炭化水素基)、−CRB 2−(RBは互いに独立に、水素原子、又は、置換又は非置換の炭素数1〜12の1価炭化水素基)、−RAr h−(RArは、炭素数6〜12の2価のアリーレン基、hは1〜6の整数)、アリーレン基から水素原子が1個又は2個脱離した3価又は4価の基、−RAr h(ORAr)i−(RArとhは前記と同定義であり、iは1〜5である。)、炭素数1〜12の直鎖状、分岐状又は環状のアルキレン基、該アルキレン基から水素原子が1個脱離した3価の基、アリーレンアルキレン基から選択される2〜4価の有機基である。)
本発明の(B)成分は、ラジカル重合性化合物であり、具体的には、(メタ)アクリル酸誘導体、アルケニル化合物、シクロアルケニル化合物、アルキニル化合物、スチリル化合物、インデニル化合物、ビニルエーテル化合物、ノルボニル化合物、及び、共役又は非共役アルカジエン化合物から選択される少なくとも一つ以上の化合物であり、その一部の水素原子がフッ素原子で置換されても良く、炭素原子が酸素原子に置換されても良い。
CH2=CR7C(=O)OR8 (4)
CH2=CR7C(=O)NR8 2 (5)
(式中、R7は、炭素数1〜10の直鎖状又は分岐状のアルキル基であり、R8は、炭素数1〜16の直鎖状、分岐状又は環状のアルキル基であり、ケイ素数2〜60のシロキサニル基を含有してもよい。なお、本明細書において、(メタ)アクリルは、アクリル及びメタクリルの双方を示す。)
本発明の(C)成分である重合開始剤は、熱分解性ラジカル開始剤、又は、放射線活性化反応剤であり、熱分解性ラジカル開始剤はアゾ化合物や有機過酸化物を用いることが可能で、この場合、熱でラジカル重合し、硬化物を形成することができる。
(D)成分の疎水性フュームドシリカは、液ダレの防止、又は塗布時の気泡の入り込み及びムラの防止、及び成形性を維持したチキソ性を示し、かつ、硬化物の高硬度化を抑えた低弾性率を示すために必須なものであり、乾燥の疎水性ヒュームドシリカ(乾式シリカ)を用いることが好ましい。上記の目的のためには嵩密度が1g/mLより低いことが好ましく、嵩密度が1g/mLより高いと調製時にシリカが沈降してしまう。更には、平均一次粒子径は1〜100nmが好ましく、平均一次粒子径が上記範囲内であると、無溶剤型シリコーン変性ポリイミド含有組成物の硬化物のフュームドシリカによる光散乱が抑えられるため、硬化物の透明性を損なうことがない。なお、この平均粒子径は、例えばレーザー光回折法等の分析手段を使用した粒度分布計により、重量平均値(又はメジアン径)等として求めることができ、例えば、株式会社キーエンスのデジタルマイクロスコープVHX−5000により測定できる。また、BET比表面積が100〜300m2/gであることが好ましい。
(式(6)中、RMAは(メタ)アクリル基を含む1価の炭化水素基である。R1、R2、R5、R6、m、及びoは前記と同定義、但し、mとoの和は3〜40の整数である。各繰り返し単位の配置はランダムに結合している。)
より好ましくは式(7)で示される化合物である。
(式(7)中、RMA、R1、R2、及び、mは前記と同定義である。)
具体的には、信越化学工業(株)製、X−22−174シリーズ(X−22−174ASX,X−22−174DX)、X−22−2404等がある。
表2に記載の組成物を少量基材上に塗布し、その上に円柱(径3mm)を乗せ、軽く密着させた後、メタルハロゲンランプにより紫外線を2,000mJ/cm2照射して作成したサンプルを、万能型ボンドテスタ(デイジ社製、4000シリーズ)を用いて測定した。
シリコーン変性ポリイミド樹脂を含有する組成物をガラス板上に厚さ1mmとなるように塗布し、メタルハライドランプを用いてUV照射(積算光量2,000mJ/m2)することにより硬化皮膜を得た。これを80℃/95%RHの高温高湿条件下、24時間曝露し、曝露前及び曝露後のガラス板との密着性を碁盤目剥離試験(JIS K5400)の方法で評価した。
撹拌羽、温度計、及び窒素導入管を取り付けた反応容器に5−(2,4−ジオキサシクロペンチル)−3a,4,5,9b−テトラヒドロナフト[1,2−c]フラン−1,3−ジオン 30.0g(0.1mol)及びN,N−ジメチルアセトアミド250g、トルエン100gを仕込み、続いて、2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン 10.3g(0.025mol)を添加し、反応温度を50℃で3時間保持した。更に下記式(i)のシロキサン66.6g(0.075mol)を室温にて滴下し、滴下終了後、室温にて12時間撹拌を行った。
次に、前記反応容器に無水酢酸20.4gとピリジン26.4gを添加し、50℃で3時間撹拌を行った。
得られた反応溶液をメタノールから再沈殿を行い、シロキサン量が26質量%のシリコーン変性ポリイミド樹脂を得た。この樹脂の赤外線吸光スペクトルを測定したところ、未反応官能基であるポリアミック酸に基づく吸収は観測されず、1,780cm-1及び1,720cm-1にイミド基に吸収を確認した。
また、GPCによりこの樹脂の重量平均分子量を測定したところ、35,000であった。石英ガラス基板上に膜厚100μmのフィルムを作成し、光線透過率を測定したところ、波長350〜450nmまでの光線透過率が80%以上であった。このフィルムの透過率スペクトルを図1に載せた。
撹拌羽、温度計、及び窒素導入管を取り付けた反応容器にジシクロヘキシル−3,4,3',4'−テトラカルボン酸二無水物30.6g(0.1mol)、及びN,N−ジメチルアセトアミド250g、トルエン100gを仕込み、続いて、2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン10.3g(0.025mol)を添加し、反応温度50℃で3時間撹拌した。更に前記式(i)のシロキサン66.6g(0.075mol)を室温で滴下し、滴下終了後室温で12時間撹拌した。
次に、前記反応容器に無水酢酸20.4gとピリジン26.4gを添加し、50℃で3時間撹拌を行った。
得られた反応溶液をメタノールから再沈殿を行い、シロキサン量が62質量%のシリコーン変性ポリイミド樹脂を得た。この樹脂の赤外線吸光スペクトルを測定したところ、未反応官能基であるポリアミック酸に基づく吸収は観測されず、1,780cm-1及び1720cm-1にイミド基に吸収を確認した。
また、GPCによりこの樹脂の重量平均分子量を測定したところ、33,000であった。石英ガラス基板上に膜厚100μmのフィルムを作成し、光線透過率を測定したところ、波長350〜450nmまでの光線透過率が80%以上であった。
撹拌羽、温度計、及び窒素導入管を取り付けた反応容器にシクロヘキサン−1,2,4,5−テトラカルボン酸二無水物22.4g(0.1mol)、及びN,N−ジメチルアセトアミド250g、トルエン100gを仕込み、続いて、2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン10.3g(0.025mol)を添加し反応温度50℃で3時間撹拌した。更に前記式(i)のシロキサン66.6g(0.075mol)を室温で滴下し、滴下終了後室温で12時間撹拌した。
次に、前記反応容器に無水酢酸20.4gとピリジン26.4gを添加し、50℃で3時間撹拌を行った。
得られた反応溶液をメタノールから再沈殿を行い、シロキサン量が67質量%のシリコーン変性ポリイミド樹脂を得た。この樹脂の赤外線吸光スペクトルを測定したところ、未反応官能基であるポリアミック酸に基づく吸収は観測されず、1,780cm-1及び1,720cm-1にイミド基に吸収を確認した。
また、GPCによりこの樹脂の重量平均分子量を測定したところ、31,000であった。石英ガラス基板上に膜厚100μmのフィルムを作成し、光線透過率を測定したところ、波長350〜450nmまでの光線透過率が80%以上であった。
撹拌羽、温度計、及び窒素導入管を取り付けた反応容器に5−(2,4−ジオキサシクロペンチル)−3a,4,5,9b−テトラヒドロナフト[1,2−c]フラン−1,3−ジオン 30.0g(0.1mol)、及びN,N−ジメチルアセトアミド250g、トルエン100gを仕込み、続いて、2,2’−[2−ヒドロキシ−3−(3,5−ジメチル−4−アミノ)−ベンジル−5−メチル]−ジフェニルメタン12.6g(0.025mol)を添加し反応温度50℃で3時間撹拌した。更に前記式(ii)のシロキサン68.6g(0.075mol)を室温で滴下し、滴下終了後室温で12時間撹拌した。
次に、前記反応容器に無水酢酸20.4gとピリジン26.4gを添加し、50℃で3時間撹拌を行った。
得られた反応溶液をメタノールから再沈殿を行い、シロキサン量が68質量%のシリコーン変性ポリイミド樹脂を得た。この樹脂の赤外線吸光スペクトルを測定したところ、未反応官能基であるポリアミック酸に基づく吸収は観測されず、1,780cm-1及び1,720cm-1にイミド基に吸収を確認した。
また、GPCによりこの樹脂の重量平均分子量を測定したところ、22,000であった。石英ガラス基板上に膜厚100μmのフィルムを作成し、光線透過率を測定したところ、波長350〜450nmまでの光線透過率が80%以上であった。
撹拌羽、温度計、及び窒素導入管を取り付けた反応容器に5−(2,4−ジオキサシクロペンチル)−3a,4,5,9b−テトラヒドロナフト[1,2−c]フラン−1,3−ジオン 30.0g(0.1mol)、及びN,N−ジメチルアセトアミド250g、トルエン100gを仕込み、続いて、2,2−ビス[4−(4−アミノフェノキシ)フェニル]プロパン 10.3g(0.025mol)を添加し反応温度50℃で3時間撹拌した。更に下記式(iii)のシロキサン105.0g(0.075mol)を室温で滴下し、滴下終了後室温で12時間撹拌した。
次に、前記反応容器に無水酢酸20.4gとピリジン26.4gを添加し、50℃で3時間撹拌を行った。
得られた反応溶液をメタノールから再沈殿を行い、シロキサン量が75質量%のシリコーン変性ポリイミド樹脂を得た。この樹脂の赤外線吸光スペクトルを測定したところ、未反応官能基であるポリアミック酸に基づく吸収は観測されず、1,780cm-1及び1,720cm-1にイミド基に吸収を確認した。
また、GPCによりこの樹脂の重量平均分子量を測定したところ、31,500であった。石英ガラス基板上に膜厚100μmのフィルムを作成し、光線透過率を測定したところ、波長350〜450nmまでの光線透過率が80%以上であった。
撹拌羽、温度計、及び窒素導入管を取り付けた反応容器に3,3',4,4'ジフェニルスルホンテトラカルボン酸二無水物 59.7g(0.167mol)、ビス[4−(3−アミノフェノキシ)フェニル]スルホン14.4g(0.033mol)、及びシクロヘキサノン400gを仕込み、続いて、前記式(i)のシロキサン118.0g(0.133mol)を、反応の内温が50℃を超えないように滴下した。滴下終了後、室温で10時間撹拌した。
次に、前記反応容器に無水酢酸40.8gとピリジン52.8gを添加し、50℃で3時間撹拌を行った。
得られた反応溶液をメタノールから再沈殿を行い、シロキサン量が61質量%のシリコーン変性ポリイミド樹脂を得た。この樹脂の赤外線吸光スペクトルを測定したところ、未反応官能基であるポリアミック酸に基づく吸収は観測されず、1,780cm-1及び1,720cm-1にイミド基に吸収を確認した。
また、GPCによりこの樹脂の重量平均分子量を測定したところ、31,000であった。石英ガラス基板上に膜厚100μmのフィルムを作成し、光線透過率を測定したところ、波長350nmから450nmまでの光線透過率が80%以下であった。
合成例1で得られたシリコーン変性ポリイミド樹脂100部に対しアクリル酸イソボルニル(IBXA)200部を加えて溶解・撹拌し、溶解物を得た。この溶解物100部に対してレオロシールDM−30S 6部、及びIrgacure1173 3部を添加し、混合撹拌を行うことで、シリコーン変性ポリイミド樹脂を含有する組成物を得た。本組成物の粘度は10Pa・sであった。このシリコーン変性ポリイミド樹脂組成物をテフロン(登録商標)板上に厚さ1mmとなるように塗布し、メタルハライドランプを用いてUV照射(積算光量2,000mJ/m2)することにより得た硬化皮膜の貯蔵弾性率は182MPaであり、L*a*b*表色系でL*96%、a*−2.6%、b*7.3%の無色であり、碁盤目試験の結果、100/100であった。
表1〜4に示す組成で、実施例1と同様に実施した。結果を同表に示す。
IBXA:アクリル酸イソボルニル
LA:アクリル酸ドデシル(ラウリルアクリレート)
Irgacure1173:BASFジャパン株式会社製
Irgacure369:BASFジャパン株式会社製
Irgacure819:BASFジャパン株式会社製
IrgacureTPO:BASFジャパン株式会社製
レオロシールDM−30S:株式会社トクヤマ製
AEROSIL R816:日本アエロジル株式会社製
X−22−174ASX:信越化学工業株式会社製
X−22−174DX:信越化学工業株式会社製
硬化性:○ 硬化
× 硬化せず
ダイシェア強度を表5,6にまとめた。
実施例5の組成物100部に改質用添加剤として、エポキシ基含有アクリレート(新中村化学(株)製、EN−1010)5部を添加し、撹拌混合し組成物34を得た。前記組成物34で碁盤目試験を行ったところ、100/100であった。また被膜の弾性率は214MPaであった。空気中で紫外線照射によるガラス基板上でガラス円柱を接着させ、ダイシェア強度を測定したところ、32.3MPaであった。
実施例1、実施例17、及び実施例18で得られた被膜の動摩擦係数を測定した。結果を表7に示す。
<動摩擦係数>
水平方向引っ張り試験機AGS−X(株式会社島津製作所製)を用いて、荷重200g、移動速度0.3m/分の条件における動摩擦係数を求めた。
シリコーン変性ポリイミド樹脂をガラス上に塗布し、硬化させた基材上に上質紙を異動させた時の動摩擦係数
実施例1の組成物に染料として和光純薬工業(株)製のRDW−B01(青色)を、シリコーン変性ポリイミド樹脂をIBXAに溶解させた溶解物100部に対して、0.005質量%を添加し、撹拌溶解させ、青色のシリコーン変性ポリイミド樹脂含有組成物を得た。本組成物の粘度は10Pa・sであった。この青色シリコーン変性ポリイミド樹脂組成物をテフロン(登録商標)板上に厚さ1mmとなるように塗布し、メタルハライドランプを用いてUV照射(積算光量2000mJ/m2)することにより得た青色の硬化皮膜の貯蔵弾性率は182MPaであり、L*a*b*表色系でL*2%、a*21.7%、b*−24.2%の青色であり、碁盤目試験の結果、100/100であった。
比較例1〜6では本発明の求める組成を満たしていないため、組成物の溶解性や粘度及び硬化性が不十分であった。これに対し、実施例1〜17の硬化皮膜は、目的の粘度範囲に収まることからチキソ性に優れ、良好な密着性及び貯蔵弾性率(MPa)を示した。
また、実施例19〜34より、本発明の組成物は窒素下及び空気中でも、ガラスや真鍮に対して良好な接着強度を示している。実施例36,37では(I)成分としてレベリング剤が添加されることで動摩擦係数が低下している。
Claims (14)
- (A)下記式(2)の両末端にそれぞれアミノ基が結合したジアミノ変性シリコーンと、不飽和結合がカルボニル基に共役していないテトラカルボン酸二無水物と、脂肪族ジアミン又は芳香族ジアミンとの反応物から得られた、下記式(1)で表されるシリコーン変性ポリイミド樹脂:100質量部、
Ee−Ff−Gg (1)
(式(1)中、FにE又はGの各繰り返し単位がランダムに結合しており、Eは式(2)に示す2価の上記ジアミノ変性シリコーン由来の残基、Fは式(3)に示す上記テトラカルボン酸二無水物由来の残基、GはEを含まない上記ジアミン由来の2価の残基である。e、f、gはそれぞれ0を超える数であってf+e+g=1であり、上記ジアミノシロキサン、テトラカルボン酸二無水物及びジアミンの物質量から換算して求められるf/(e+g)のmol比が0.8〜1.2である。)
−Im−X−Im− (3)
(式(3)中、Imは環状イミド構造を端に含む環状の基であり、Xは単結合、酸素、硫黄、スルフィド基、スルホン基、カルボニル基、−NRN−(RNは炭素数1〜12の直鎖状、分岐状又は環状の1価炭化水素基)、−CRB 2−(RBは互いに独立に、水素原子、又は、置換又は非置換の炭素数1〜12の1価炭化水素基)、−RAr h−(RArは、炭素数6〜12の2価のアリーレン基、hは1〜6の整数)、アリーレン基から水素原子が1個又は2個脱離した3価又は4価の基、−RAr h(ORAr)i−(RArとhは前記と同定義であり、iは1〜5である。)、炭素数1〜12の直鎖状、分岐状又は環状のアルキレン基、該アルキレン基から水素原子が1個脱離した3価の基、アリーレンアルキレン基から選択される2〜4価の有機基である。)
(B)下記式(4')で表される(メタ)アクリル酸エステル化合物:100〜2,000質量部、
CH2=CR7C(=O)OR8 (4’)
(式中、R7は、炭素数1〜10の直鎖状又は分岐状のアルキル基であり、R8は、炭素数9〜16の直鎖状、分岐状又は環状のアルキル基である。)
(C)重合開始剤:(A)及び(B)成分の合計100質量部に対して0.1〜30質量部、
(D)疎水性フュームドシリカ:(A)及び(B)成分の合計100質量部に対して1〜50質量部
を含有してなり、25℃において流動性を有し、かつ溶剤を含まないことを特徴とする無溶剤型シリコーン変性ポリイミド樹脂組成物。 - (B)成分が(メタ)アクリル酸イソボルニル、(メタ)アクリル酸ノニル、(メタ)アクリル酸デシル、(メタ)アクリル酸ウンデシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸トリデシル、(メタ)アクリル酸テトラデシル、(メタ)アクリル酸ペンタデシル又は(メタ)アクリル酸ヘキサデシルである請求項1又は2に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- (B)成分の配合量が(A)成分100質量部に対して100〜500質量部である請求項1〜3のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- (C)成分が、熱分解性ラジカル開始剤、又は、放射線活性化開始剤である請求項1〜4のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- (D)成分が、嵩密度が1g/mLより低く、平均一次粒子径が1〜100nmであり、BET比表面積が100〜300m2/gである疎水性フュームドシリカである請求項1〜5のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- 無溶剤型シリコーン変性ポリイミド樹脂組成物の25℃における粘度が3〜1,000Pa・sである請求項1〜6のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- (H)成分としてエポキシ基含有アクリレートからなる接着強度改質用添加剤を含有する請求項1〜7のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- (I)成分として(メタ)アクリル酸変性シリコーンからなるレベリング剤を含有する請求項1〜8のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- (J)成分として染料を含有する請求項1〜9のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物。
- 請求項1〜10のいずれか1項に記載の組成物からなる接着剤。
- 請求項1〜10のいずれか1項に記載の組成物からなるコーティング剤。
- 請求項1〜10のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物を紫外線及び/又は可視光で硬化させた皮膜の貯蔵弾性率が1MPa以上500MPa以下であるシリコーン変性ポリイミド樹脂硬化物。
- 請求項1〜9のいずれか1項に記載の無溶剤型シリコーン変性ポリイミド樹脂組成物を紫外線及び/又は可視光で硬化させた被膜が、可視光領域の波長で光透過率が80%以上であり、L*a*b*表色系でL*が80%以上、a*が−10%以上10%未満、b*が−10%以上10%未満であるシリコーン変性ポリイミド樹脂硬化物。
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