JP6390233B2 - 硬化性樹脂組成物 - Google Patents
硬化性樹脂組成物 Download PDFInfo
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- JP6390233B2 JP6390233B2 JP2014148713A JP2014148713A JP6390233B2 JP 6390233 B2 JP6390233 B2 JP 6390233B2 JP 2014148713 A JP2014148713 A JP 2014148713A JP 2014148713 A JP2014148713 A JP 2014148713A JP 6390233 B2 JP6390233 B2 JP 6390233B2
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- polyester
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- 239000011342 resin composition Substances 0.000 title claims description 29
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- 239000011347 resin Substances 0.000 claims description 59
- -1 silane compound Chemical class 0.000 claims description 51
- 229920000728 polyester Polymers 0.000 claims description 48
- 229920002050 silicone resin Polymers 0.000 claims description 38
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229910000077 silane Inorganic materials 0.000 claims description 21
- 238000010521 absorption reaction Methods 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 16
- 125000005372 silanol group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 10
- 239000000853 adhesive Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- 239000004611 light stabiliser Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 235000021388 linseed oil Nutrition 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
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- 229910052726 zirconium Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000001273 butane Substances 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
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- 125000002723 alicyclic group Chemical group 0.000 description 2
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
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- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- LOMJGCFEVIUZMW-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-(2-ethylhexoxy)-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(OCC(CC)CCCC)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C LOMJGCFEVIUZMW-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
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Description
酸化チタンは、ルチル型、アナターゼ型、ブルッカイト型の3種類の結晶構造を有するが、本発明に用いる酸化チタンは、ルチル型酸化チタンであることが必要である。ルチル型酸化チタンは最も安定した結晶構造であるので、高耐熱性(300℃×30分間)を有する硬化性樹脂組成物を得ることができる。
式:d=6/(ρ・a)
(dは平均粒子径(μm)、ρは二酸化チタンの比重である。)
式:吸油量(g/100g)=アマニ油の量(g)×100/試料(g)
本発明に用いる硬化性樹脂は、特に限定されないが、エステル結合とシロキサン結合を有する硬化性樹脂であることが好ましい。なかでもポリエステル(a)と、シリコーン樹脂(b)と、シラン化合物(c)を反応させてなる硬化性樹脂であることが好ましく、より好ましくは未反応のアルコキシ基が1分子あたり0.1〜30個含有する硬化性樹脂である。このような硬化性樹脂を用いることによって、優れた高耐熱性(300℃×30分間)および密着性を有する硬化性樹脂組成物を得ることができる。
<ポリエステル(a)>
シリコーン樹脂(b)は、特に限定されないが、反応活性基としてシラノール基および/またはアルコキシ基を有する樹脂であることが好ましい。シリコーン樹脂(b)におけるシラノール基およびアルコキシ基の少なくとも一方の含有量は1〜20重量%が好ましく、2〜17重量%がより好ましい。1重量%未満であると、ポリエステル(a)との反応が不足し重合体を得にくくなることがあり、20重量%を超えると分岐構造が多くなりすぎ、重合体がゲル化する可能性があるため、好ましくない。
シラン化合物(c)は、特に限定されないが、下記式(1)で示される構造のシラン化合物であることが好ましい。式(1)構造のシラン化合物を用いることで硬化性、密着性、耐熱性のいずれも満足することができ、式(1)構造のものでない場合、硬化性、密着性、耐熱性のいずれか1以上が劣る傾向にある。
本発明の硬化性樹脂組成物は、前記酸化チタン(A)と硬化性樹脂(B)を含有する組成物である。
ポリエステルおよび硬化性樹脂の試料を、重クロロホルムに溶解し、VARIAN社製 NMR装置400−MRを用いて、1H−NMR分析を行ってその積分値比より、モル比を求めた。
ポリエステルおよび硬化性樹脂の試料を、樹脂濃度が0.5重量%程度となるようにテトラヒドロフランで溶解および/または希釈し、孔径0.5μmのポリ四フッ化エチレン製メンブレンフィルターで濾過したものを測定用試料として、テトラヒドロフランを移動相とし、示差屈折計を検出器とするゲル浸透クロマトグラフィー(GPC)により分子量を測定した。流速は1mL/分、カラム温度は30℃とした。カラムには昭和電工製KF−802、804L、806Lを用いた。分子量標準には単分散ポリスチレンを使用した。
ポリエステルの試料0.1gをフェノール/テトラクロロエタン(重量比6/4)の混合溶媒25ccに溶解し、30℃で測定した。
ポリエステルの試料0.2gを40mlのクロロホルムに溶解し、0.01Nの水酸化カリウムエタノール溶液で滴定し、カルボキシル基含有樹脂106gあたりの当量(eq/t)を求めた。指示薬にはフェノールフタレインを用いた。
硬化性樹脂ワニスと酸化チタンを表3に示す重量比で配合し、ブチルカルビトールアセテートを用いて固形分濃度を60重量%に調整した後、2mmφガラスビーズを加えペイントシェーカーで12時間分散処理を行なった。
ガラス板(125mm×125mm×1mm)の片面に、(5)で作製した塗料を乾燥後の膜厚が10〜20μmになるようにワイヤーバーで塗布し、熱硬化条件160℃×30分間として熱風乾燥機を用いて熱処理を行い、これを試験片とした(以下、試験片という)。
試験片を、JIS−K5600−5−6:1999に準拠して、1mmの碁盤目を100ヶ所作り、セロテープ(登録商標)による剥離試験をおこない碁盤目の剥離状態を観察した。
判定基準
○:100/100で剥離なし
△:70〜99/100
×:0〜69/100
試験片を、耐熱性評価条件300℃×30分間として熱風乾燥機を用いて熱処理を行った。測色色差計Color Meter ZE 2000(日本電色工業(株)製)を用い、熱処理前後の試験片を、試験片の硬化性樹脂層側からJIS−Z8722記載の方法に従って測定し、L*a*b*表色系で表したときのΔb値で評価した。Δb値とは、耐熱性試験前後のb値の差(試験後のb値−試験前のb値)をいう。
判定基準
◎:Δb値0.04未満
○:Δb値0.04以上0.50未満
△:Δb値0.50以上1.00未満
×:Δb値1.00以上
攪拌機、コンデンサー、温度計を具備した10L四つ口フラスコに、テレフタル酸697重量部、イソフタル酸1510重量部、無水トリメリト酸134重量部、エチレングリコール1042重量部、ネオペンチルグリコール1165重量部、触媒としてテトラ−n−ブチルチタネート(以下、TBTと略記する場合がある)0.95重量部(全酸成分に対して0.02モル%)を仕込み、4時間かけて240℃まで徐々に昇温しながら、エステル化反応を行った。次いで、系内を徐々に減圧していき、30分かけて10mmHgまで減圧して初期重合を行うとともに温度を250℃まで昇温し、さらに1mmHg以下の真空下で10分間後期重合を行ない、本発明のポリエステル(合成例(1))を得た。得られたポリエステルの数平均分子量は3,000、還元粘度は0.17dl/g、酸価は20eq/tであった。
合成例(1)と同様に直接重合法にて、但し仕込み組成を変更して、樹脂組成が表1に示されるような本発明のポリエステル(合成例(2)、(3))を製造した。
攪拌機、コンデンサー、温度計を具備した10L四つ口フラスコに、イソフタル酸1955重量部、アジピン酸191重量部、2−メチル−1,3−プロパンジオール1531重量部、ネオペンチルグリコール817重量部、トリメチロールプロパン175重量部、触媒としてTBT0.89重量部(全酸成分に対して0.02モル%)を仕込み、4時間かけて240℃まで徐々に昇温しながら、エステル化反応を行った。次いで、系内を徐々に減圧していき、30分かけて10mmHgまで減圧して初期重合を行うとともに温度を250℃まで昇温し、さらに1mmHg以下の真空下で12分間後期重合を行なった。次いで、常圧に戻したのち、30分かけて220℃まで冷却し、無水トリメリト酸50重量部を加え220℃で30分かけて反応を行い、本発明のポリエステル(合成例(4))を得た。得られたポリエステルの数平均分子量は4,000、還元粘度は0.20dl/g、酸価は250eq/tであった。
攪拌機、コンデンサー、温度計を具備した10L四つ口フラスコに、テレフタル酸ジメチル820重量部、イソフタル酸ジメチル1777重量部、無水トリメリト酸135重量部、エチレングリコール1048重量部、ネオペンチルグリコール1172重量部、触媒としてTBT0.96重量部(全酸成分に対して0.02モル%)を仕込み、4時間かけて220℃まで徐々に昇温しながら、エステル化反応を行った。次いで、系内を徐々に減圧していき、30分かけて10mmHgまで減圧して初期重合を行うとともに温度を250℃まで昇温し、さらに1mmHg以下の真空下で10分間後期重合を行ない、本発明のポリエステル(合成例(5))を得た。直接重合法で得られた合成例(1)の性能と差異はなく、組成と特性値を表1に示す。
攪拌機、ディーンスターク装置、温度計を具備した1L四つ口フラスコに、ブチルカルビトールアセテート242重量部を加え、80℃まで加熱した。次いで、合成例(1)のポリエステル66重量部、217 FLAKE RESIN(東レダウコーニング社製シリコーンレジン、シラノール基含有量6重量%)210重量部を添加して攪拌し、溶解した。その後1時間かけて200℃まで徐々に昇温し、脱水反応を行った。溜出した水の量が、反応率が45%となる1.36重量部になったことを確認したのち30分かけて150℃まで降温した。次いでn−デシルトリメトキシシラン24重量部を添加し、150℃で脱アルコール反応を行った。溜出したメタノールの量が、反応率が34%となる3.00重量部になったことを確認したのち1時間かけて室温まで冷却し、ブチルカルビトールアセテートを加えて固形分を50重量%に調整し、本発明の硬化性樹脂のワニス(製造例(1))を得た。得られた硬化性樹脂の数平均分子量は4,000、未反応のアルコキシ基残存個数は2.4個/分子であった。
製造例(1)と同様にして、但し仕込み組成を変更して、樹脂組成が表2に示されるような本発明の硬化性樹脂ワニス(製造例(2)〜(7))を製造した。
Z−6018:東レダウコーニング(株)製シリコーンレジン、数平均分子量2,000、シラノール基含有量6重量%
217 FLAKE RESIN:東レダウコーニング(株)製シリコーンレジン、数平均分子量2,000、シラノール基含有量6重量%
220 FLAKE RESIN:東レダウコーニング(株)製シリコーンレジン、数平均分子量3,000、シラノール基含有量6重量%
233 FLAKE RESIN:東レダウコーニング(株)製シリコーンレジン、数平均分子量3,000、シラノール基含有量6重量%
3074 INTERMEDIATE:東レダウコーニング(株)製シリコーンレジン、数平均分子量1,400、メトキシ基含有量17重量%
製造例(1)の硬化性樹脂ワニス(固形分として100重量部)と酸化チタン(UT−771)40重量部を配合し、ブチルカルビトールアセテートを用いて固形分濃度を60重量%に調整した。その後、2mmφガラスビーズを加えペイントシェーカーで12時間分散処理し、塗料(1)を作製した。塗料(1)を用いて、前述の方法により試験片を作製した。試験片を評価した結果を表3に示した。
実施例(1)と同様にして、前述した方法により塗料を塗布、熱処理を行い本発明の塗装ガラス板の試験片を得た。試験片を評価した結果を表3に示した。
UT−771:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、Zr、有機、シリカ処理なし)、平均粒子径0.25μm、吸油量17g/100g
PF−739:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、Zr、有機、シリカ処理なし)、平均粒子径0.25μm、吸油量14g/100g
CR−50−2:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、有機、シリカ処理なし)、平均粒子径0.25μm、吸油量17g/100g
CR−58−2:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、有機、シリカ処理なし)、平均粒子径0.28μm、吸油量18g/100g
CR−60−2:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、有機、シリカ処理なし)、平均粒子径0.21μm、吸油量14g/100g
CR−63:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、SiO2)、平均粒子径0.21μm、吸油量14g/100g
CR−93:石原産業(株)製ルチル型酸化チタン、表面処理種(Al、SiO2)、平均粒子径0.28μm、吸油量20g/100g
JR−701:テイカ(株)製ルチル型酸化チタン、表面処理種(Al、SiO2、Zn)、平均粒子径0.27μm、吸油量20g/100g
JR−806:テイカ(株)製ルチル型酸化チタン、表面処理種(Al、SiO2)平均粒子径0.25μm、吸油量21g/100g
TI−PURE R−960:デュポン(株)製ルチル型酸化チタン、表面処理種(Al、SiO2)平均粒子径0.50μm、吸油量19g/100g
Claims (6)
- 平均粒子径1μm以下、吸油量19g/100g以下であり、かつ表面がシリカ処理されていないルチル型酸化チタン(A)と、硬化性樹脂(B)を含む硬化性樹脂組成物であって、
硬化性樹脂(B)が、ポリエステル(a)と、シリコーン樹脂(b)と、下記式(1)で示されるシラン化合物(c)の反応物であり、未反応のアルコキシ基が1分子あたり0.1〜30個含有する硬化性樹脂組成物。
- 硬化性樹脂(B)が、エステル結合およびシロキサン結合を有する請求項1に記載の硬化性樹脂組成物。
- 前記シリコーン樹脂(b)の数平均分子量が500〜5,000であり、かつシラノール基およびアルコキシ基の少なくとも一方を1〜20重量%含有する請求項1または2に記載の硬化性樹脂組成物。
- シリコーン樹脂(b)が下記式(2)〜(4)で示される構造単位のいずれか1以上を含む請求項1〜3のいずれか1項に記載の硬化性樹脂組成物。
- 請求項1〜4のいずれか1項に記載の硬化性樹脂組成物を含むインキ。
- 請求項1〜4のいずれか1項に記載の硬化性樹脂組成物を含む接着剤。
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