JP4410540B2 - フルオレン骨格含有樹脂組成物およびその成形体 - Google Patents
フルオレン骨格含有樹脂組成物およびその成形体 Download PDFInfo
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- JP4410540B2 JP4410540B2 JP2003400448A JP2003400448A JP4410540B2 JP 4410540 B2 JP4410540 B2 JP 4410540B2 JP 2003400448 A JP2003400448 A JP 2003400448A JP 2003400448 A JP2003400448 A JP 2003400448A JP 4410540 B2 JP4410540 B2 JP 4410540B2
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- Prior art keywords
- bis
- fluorene
- resin
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- fluorenes
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 32
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title claims description 25
- -1 trihydroxyphenyl Chemical group 0.000 claims description 107
- 125000002947 alkylene group Chemical group 0.000 claims description 59
- 229920005989 resin Polymers 0.000 claims description 46
- 239000011347 resin Substances 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229920005992 thermoplastic resin Polymers 0.000 claims description 34
- 150000002220 fluorenes Chemical class 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 27
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 25
- 239000000049 pigment Substances 0.000 claims description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 7
- 239000004431 polycarbonate resin Substances 0.000 claims description 6
- 229920005668 polycarbonate resin Polymers 0.000 claims description 6
- 229920001225 polyester resin Polymers 0.000 claims description 6
- 239000004645 polyester resin Substances 0.000 claims description 5
- 229920001721 polyimide Polymers 0.000 claims description 5
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 239000003575 carbonaceous material Substances 0.000 claims description 4
- 239000009719 polyimide resin Substances 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 229920005749 polyurethane resin Polymers 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 229920001281 polyalkylene Polymers 0.000 claims description 3
- 229920001230 polyarylate Polymers 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 2
- KZQIIFWNIUXCCN-UHFFFAOYSA-N 4-(9H-fluoren-1-yl)benzene-1,2,3-triol Chemical class OC1=C(C(=C(C=C1)C1=CC=CC=2C3=CC=CC=C3CC12)O)O KZQIIFWNIUXCCN-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 198
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 39
- PTBCCLLVPOLXES-UHFFFAOYSA-N 2-[9-(2-hydroxyphenyl)fluoren-9-yl]phenol Chemical class OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)C2=CC=CC=C2C2=CC=CC=C21 PTBCCLLVPOLXES-UHFFFAOYSA-N 0.000 description 25
- 125000003545 alkoxy group Chemical group 0.000 description 25
- 239000000975 dye Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 125000003277 amino group Chemical group 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- 239000003063 flame retardant Substances 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000010408 film Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 13
- GYLHMFMJRFZBBW-UHFFFAOYSA-N 3-[9-(2,3-dihydroxyphenyl)fluoren-9-yl]benzene-1,2-diol Chemical class OC1=CC=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C(=C(O)C=CC=2)O)=C1O GYLHMFMJRFZBBW-UHFFFAOYSA-N 0.000 description 11
- 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 11
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- QDMXRSFKPPVBDW-UHFFFAOYSA-N 2-[9-(2-aminophenyl)fluoren-9-yl]aniline Chemical class NC1=CC=CC=C1C1(C=2C(=CC=CC=2)N)C2=CC=CC=C2C2=CC=CC=C21 QDMXRSFKPPVBDW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 6
- 125000005037 alkyl phenyl group Chemical group 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 229920000049 Carbon (fiber) Polymers 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- GGANEIOSDSVALY-UHFFFAOYSA-N 4-[9-(2,3,4-trihydroxyphenyl)fluoren-9-yl]benzene-1,2,3-triol Chemical class OC1=C(C=CC(=C1O)O)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=C(C(=C(C=C1)O)O)O GGANEIOSDSVALY-UHFFFAOYSA-N 0.000 description 4
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical class C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000004419 Panlite Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000004734 Polyphenylene sulfide Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 238000006664 bond formation reaction Methods 0.000 description 4
- 239000004917 carbon fiber Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 229920000069 polyphenylene sulfide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- GIXNHONPKYUROG-UHFFFAOYSA-N 4-(9h-fluoren-1-yl)phenol Chemical class C1=CC(O)=CC=C1C1=CC=CC2=C1CC1=CC=CC=C12 GIXNHONPKYUROG-UHFFFAOYSA-N 0.000 description 3
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000001007 phthalocyanine dye Substances 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 235000014692 zinc oxide Nutrition 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 2
- HGRZLIGHKHRTRE-UHFFFAOYSA-N 1,2,3,4-tetrabromobutane Chemical compound BrCC(Br)C(Br)CBr HGRZLIGHKHRTRE-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XTIUBELQKDSHEO-UHFFFAOYSA-N 2-[[2-[9-[2-(oxiran-2-ylmethoxy)phenyl]fluoren-9-yl]phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C1(C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1OCC1CO1 XTIUBELQKDSHEO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052581 Si3N4 Inorganic materials 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
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- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 150000002009 diols Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000012796 inorganic flame retardant Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
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- 239000001023 inorganic pigment Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
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- 239000012046 mixed solvent Substances 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920001643 poly(ether ketone) Polymers 0.000 description 2
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- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
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- 150000003573 thiols Chemical class 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
前記式(1)において、反応性基は、ヒドロキシル基、アミノ基などの活性水素を含有する基、これらの活性水素を通じて得られた基などであってもよい。具体的には、式(1)において、基R1及びR2が、同一又は異なって、アルキル基、アリール基、アラルキル基、ヒドロキシル基、アミノ基、又は基−[X−(R5O)n−Y](式中、R5は、アルキレン基であり、基Xは、酸素原子又はイミノ基であり、基Yは水素原子、グリシジル基又は(メタ)アクリロイル基であり、nは0又は1以上の整数を示す。ただし、nが0であるとき、Yは水素原子でない)であり、基R1及びR2が、少なくともヒドロキシル基、アミノ基又は前記基−[X−(R5O)n−Y]を含み、k1およびk2が1〜3であり、m1およびm2が0であってもよい。
フルオレン骨格を有する化合物(以下、単にフルオレン化合物ということがある)は、下記式(1)で表される。
非反応性基としては、特に限定されないが、例えば、アルキル基(メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、s−ブチル基、t−ブチル基などのC1-20アルキル基、好ましくはC1-8アルキル基、さらに好ましくはC1-6アルキル基など)、シクロアルキル基(シクロペンチル基、シクロへキシル基などのC5-10シクロアルキル基、好ましくはC5-8シクロアルキル基、さらに好ましくはC5-6シクロアルキル基など)、アリール基[フェニル基、アルキルフェニル基(メチルフェニル基(トリル基)、ジメチルフェニル基(キシリル基)など)などのC6-10アリール基、好ましくはC6-8アリール基、特にフェニル基など)、アラルキル基(ベンジル基、フェネチル基などのC6-10アリール−C1-4アルキル基など)などの炭化水素基;アルコキシ基(メトキシ基などのC1-4アルコキシ基など);アシル基(アセチル基などのC1-6アシル基など);アルコキシカルボニル基(メトキシカルボニル基などのC1-4アルコキシカルボニル基など);N,N−二置換アミノ基[例えば、炭化水素基で置換されたアミノ基(ジメチルアミノ基などのN,N−ジC1-6アルキルアミノ基など)];ハロゲン原子(フッ素原子、塩素原子など);ニトロ基;シアノ基などが挙げられる。
(1a)9,9−ビス(ヒドロキシフェニル)フルオレン類には、9,9−ビス(モノヒドロキシフェニル)フルオレン類、9,9−ビス(ジヒドロキシフェニル)フルオレン類、9,9−ビス(トリヒドロキシフェニル)フルオレン類などが含まれる。
9,9−ビス(ヒドロキシフェニル)フルオレン類のアルキレンオキシド付加体としては、前記例示のビス(モノ乃至トリヒドロキシフェニル)フルオレン類にアルキレンオキシド(C2-4アルキレンオキシド、特にC2-3アルキレンオキシド)が付加した化合物が挙げられる。アルキレンオキシド単位の付加数(前記式におけるn)は、前記と同様(例えば、1〜12、好ましくは1〜8、さらに好ましくは1〜6、特に1〜4程度)であり、特に限定されないが、以下に、一例として、nが1又は2の化合物を例示する。
9,9−ビス(ヒドロキシフェニル)フルオレン類のグリシジルエーテルとしては、前記例示の9,9−ビス(ヒドロキシフェニル)フルオレン類のグリシジルエーテル類が挙げられる。
9,9−ビス(ヒドロキシフェニル)フルオレン類の(メタ)アクリレートとしては、前記例示の9,9−ビス(ヒドロキシフェニル)フルオレン類の(メタ)アクリレートが挙げられる。
9,9−ビス(アミノフェニル)フルオレン類としては、前記9,9−ビス(ヒドロキシフェニル)フルオレン類に対応する化合物、すなわち、9,9−ビス(ヒドロキシフェニル)フルオレン類のヒドロキシル基が、アミノ基又はN−置換アミノ基である化合物などが挙げられる。
ポリカーボネート(帝人化成(株)製 パンライトAD5503)100重量部とビスフェノールフルオレンジグリシジルエーテル(大阪ガスケミカル(株)製)40重量部をモノクロロベンゼン/ジクロロメタン(混合比1/1)の混合溶媒に固形分濃度が20重量%となるように溶解し、その後、この溶液を用いて、ガラス基板上にキャスト膜を形成した。100℃で2時間加温して、溶媒を除去し、ガラス基板上から剥がすことによりキャストフィルムを形成した。得られたキャストフィルムは、無色透明であった。得られたフィルムの屈折率をアッベ屈折率計(アタゴ(株)製)で測定したところ1.59であった。
ポリカーボネート(帝人化成(株)製 パンライトAD5503)100重量部をモノクロロベンゼン/ジクロロメタン(混合比1/1)の混合溶媒に固形分濃度が20重量%となるように溶解し、その後、この溶液を用いて、ガラス基板上にキャスト膜を形成した。100℃で2時間加温して、溶媒を除去し、ガラス基板上から剥がすことによりキャストフィルムを形成した。得られたキャストフィルムは、無色透明であった。得られたフィルムの屈折率をアッベ屈折率計(アタゴ(株)製)で測定したところ1.58であった。
ポリカーボネート(帝人化成(株)製 パンライトAD5503)100重量部とビスフェノールフルオレンジグリシジルエーテル(大阪ガスケミカル(株)製)30重量部をドライブレンドし、押出機(テクノベル(株)製 20mm押出機)を用いて樹脂温度270℃で溶融混練し、樹脂ペレットを得た。次に、得られた樹脂ペレットを用いて、樹脂温度290℃で、卓上型ホットプレス機(神藤金属工業(株)製、型式NSF−50)で成形したところ、透明なプレート(厚み0.1mm)を得ることができた。
ポリカーボネート(帝人化成(株)製 パンライトAD5503)100重量部とビスフェノールフルオレンジグリシジルエーテル(大阪ガスケミカル(株)製)40重量部をシクロペンタノン(和光純薬(株)製)400重量部に溶かし、色素として、「IRG022」(日本化薬(株)製)3.5重量部、「MIR101」(みどり化学(株)製)1.2重量部、「810K」(日本触媒(株)製)1.2重量部を加えて、溶解した。その後、得られた溶液を用いて、ガラス基板上にスピンコート膜(0.5μm)を形成した。100℃で2時間加温して、溶媒を除去し、1000nmの透過率を測定したところ、透過率が30%以下であった。
ビスフェノールフルオレンジグリシジルエーテル(大阪ガスケミカル(株)製)の代わりにビスフェノキシエタノールフルオレン(大阪ガスケミカル(株)製)を用いる以外は実施例1と同様にしたところ、無色透明のキャスト膜が得られた。
ビスフェノールフルオレンジグリシジルエーテル(大阪ガスケミカル(株)製)の代わりにビスフェノキシエタノールジアクリレート(9,9−ビス(4−(2−アクリロイルオキシエトキシ)フェニル)フルオレン、大阪ガスケミカル(株)製)を用いる以外は実施例1と同様にしたところ、無色透明のキャスト膜が得られた。
Claims (5)
- フルオレン骨格を有する化合物と、熱可塑性樹脂とで構成された樹脂組成物であって、
前記フルオレン骨格を有する化合物が、(i)9,9−ビス(モノ乃至トリヒドロキシフェニル)フルオレン類又はそのC 2−4 アルキレンオキシド付加体のグリシジルエーテル、及び(ii)9,9−ビス(モノ乃至トリヒドロキシフェニル)フルオレン類又はそのC 2−4 アルキレンオキシド付加体の(メタ)アクリレートから選択された少なくとも1種であり、
前記熱可塑性樹脂が、ポリエステル系樹脂、ポリウレタン系樹脂、ポリカーボネート系樹脂、アクリル系樹脂、およびポリイミド系樹脂から選択された少なくとも1種であり、
前記フルオレン骨格を有する化合物の割合が、前記熱可塑性樹脂100重量部に対して、5〜60重量部である樹脂組成物。 - フルオレン骨格を有する化合物が、9,9−ビス(モノ乃至トリヒドロキシフェニル)フルオレン類又はそのC2−4アルキレンオキシド付加体のグリシジルエーテルである請求項1記載の樹脂組成物。
- 熱可塑性樹脂が、芳香族ポリカーボネート系樹脂、ポリアルキレンアリレート系樹脂、および芳香族ジカルボン酸と芳香族ジオールを重合成分として用いたポリアリレート系樹脂から選択された少なくとも1種である請求項1記載の樹脂組成物。
- さらに、機能発現剤又は添加剤として、カーボン材料、機能性色素、および機能性顔料から選択された少なくとも1種の芳香環を有する化合物を、熱可塑性樹脂100重量部に対して0.1〜40重量部含む請求項1記載の樹脂組成物。
- 請求項1記載の樹脂組成物で形成された成形体。
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