JP5790980B2 - チオール基含有ポリマー及びその硬化型組成物 - Google Patents
チオール基含有ポリマー及びその硬化型組成物 Download PDFInfo
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- JP5790980B2 JP5790980B2 JP2013546109A JP2013546109A JP5790980B2 JP 5790980 B2 JP5790980 B2 JP 5790980B2 JP 2013546109 A JP2013546109 A JP 2013546109A JP 2013546109 A JP2013546109 A JP 2013546109A JP 5790980 B2 JP5790980 B2 JP 5790980B2
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- 239000000203 mixture Substances 0.000 title claims description 41
- 125000003396 thiol group Chemical group [H]S* 0.000 title claims description 36
- 230000005484 gravity Effects 0.000 claims description 38
- 230000009477 glass transition Effects 0.000 claims description 31
- 230000004580 weight loss Effects 0.000 claims description 19
- 239000003822 epoxy resin Substances 0.000 claims description 16
- 229920000647 polyepoxide Polymers 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 229920001021 polysulfide Polymers 0.000 description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 35
- 229910052717 sulfur Inorganic materials 0.000 description 33
- 239000011593 sulfur Substances 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 27
- 239000005077 polysulfide Substances 0.000 description 18
- 150000008117 polysulfides Polymers 0.000 description 18
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 16
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
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- -1 trihaloalkyl compound Chemical class 0.000 description 14
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- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 12
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- NLXGURFLBLRZRO-UHFFFAOYSA-N 1-chloro-2-(2-chloroethoxymethoxy)ethane Chemical compound ClCCOCOCCCl NLXGURFLBLRZRO-UHFFFAOYSA-N 0.000 description 10
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 10
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- 125000000962 organic group Chemical group 0.000 description 8
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
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- 239000003963 antioxidant agent Substances 0.000 description 6
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- LULCPJWUGUVEFU-UHFFFAOYSA-N Phthiocol Natural products C1=CC=C2C(=O)C(C)=C(O)C(=O)C2=C1 LULCPJWUGUVEFU-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
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- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- 235000012255 calcium oxide Nutrition 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- PGAXJQVAHDTGBB-UHFFFAOYSA-N dibutylcarbamothioylsulfanyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SSC(=S)N(CCCC)CCCC PGAXJQVAHDTGBB-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000012847 fine chemical Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
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- 239000002245 particle Substances 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 239000013585 weight reducing agent Substances 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
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- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-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
- 235000019738 Limestone Nutrition 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
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- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
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- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical class OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229960001841 potassium permanganate Drugs 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- UHCGLDSRFKGERO-UHFFFAOYSA-N strontium peroxide Chemical compound [Sr+2].[O-][O-] UHCGLDSRFKGERO-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LAJZODKXOMJMPK-UHFFFAOYSA-N tellurium dioxide Chemical compound O=[Te]=O LAJZODKXOMJMPK-UHFFFAOYSA-N 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-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
- 239000013638 trimer Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- 239000012991 xanthate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/14—Polysulfides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/12—Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/14—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/52—Polythioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4028—Isocyanates; Thioisocyanates
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/04—Polysulfides
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/02—Polythioethers; Polythioether-ethers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
HS−(R−Sr)n−R−SH
(Rが−C 2 H 4 −O−CH 2 −O−C 2 H 4 −を50モル%以上含む有機基及び/又は下記の分岐アルキレン基
チオール基含有ポリマーである。
HS−(R−Sr)n−R−SH
(Rが−C 2 H 4 −O−CH 2 −O−C 2 H 4 −を50モル%以上含む有機基及び/又は下記の分岐アルキレン基
チオール基含有ポリマーである。
−C 2 H 4 −O−CH 2 −O−C 2 H 4 −
を50モル%以上含む有機基と、分岐アルキレン基を含む有機基である。分岐アルキレン基は、好ましくは、−O−CH2−O−結合のモル数に対して、0〜70モル%である。
−C2H4−O−CH2−O−C2H4−
を50モル%以上含有する。好ましくは、
−C2H4−O−CH2−O−C2H4−
を70モル%以上含有する。
HS−(R−Sr)n−R−SH
のrは、1〜5の整数であり、好ましくは、1〜3の整数である。rの平均値は、1.1以上1.8以下である。rの平均値が1.1未満である場合、ポリスルフィド結合による紫外線吸収性が低下し硬化後の耐候性や硬度が乏しくなる。また、rの平均値が1.8を超える場合は、顕著な低粘度、低比重、低ガラス転移温度、高耐熱性などの効果が得られない。
HS−(R−Sr)n−R−SH
における硫黄の平均値rが1.1以上1.8以下である。
HS−(R−Sr)n−R−SH
(Rが−C 2 H 4 −O−CH 2 −O−C 2 H 4 −を50モル%以上含む有機基及び/又は下記の分岐アルキレン基
チオール基含有ポリマーと、酸化剤を含有する。
HS−(R−Sr)n−R−SH
(Rが−C 2 H 4 −O−CH 2 −O−C 2 H 4 −を50モル%以上含む有機基及び/又は下記の分岐アルキレン基
チオール基含有ポリマーと、分子中に2個以上のイソシアネート基含有化合物を含有する。
HS−(R−Sr)n−R−SH
(Rが−C 2 H 4 −O−CH 2 −O−C 2 H 4 −を50モル%以上含む有機基及び/又は下記の分岐アルキレン基
チオール基含有ポリマーと、分子中に2個以上のグリシジル基を含有するエポキシ樹脂とアミン類を含有する。
試料をトルエンとピリジンの混合溶液に溶解し、ヨウ化カリウム水溶液を加えた後にヨウ素標準溶液を用いて滴定した。
東機産業製粘度計U−EIIを用いて25℃でのサンプル粘度を測定した。
23℃の雰囲気下で、比重測定用容器を用いて、23℃で24時間以上養生した蒸留水ならびにポリマーの質量を測定した。水の比重が1.0であると仮定して、容量に対するポリマー質量から、ポリマー比重を算出した。
23℃の雰囲気下で、空気中と水中での質量を測定し、以下の式により
比重=空気中での質量/(空気中での質量−水中での質量)
比重を算出した。
TAInstruments製示差走査熱量計DSCQ10を用いて、約10mgのサンプルを―90℃から10℃まで、窒素雰囲気下で10℃/分で等速昇温した。得られたDSC曲線の階段状シグナルからTgを求めた。
TAInstruments製熱重量測定装置TGAQ50を用いて、約30mgのサンプルを室温から500℃まで、窒素雰囲気下で10℃/分で等速昇温した。得られたTGA曲線において、重量が初期重量の50%になる温度を50%重量減少温度とした。
下記のチオール基含有ポリマーの場合は
HS−(R−Sr)n−R−SH
(ここで、Rは−C2H4−O−CH2−O−C2H4−、nが1〜200の整数である)、rが2、すなわち、ジスルフィド結合を有する場合には、13C−NMR分析を行うと、38.6〜38.8ppm付近に強いピークが存在する。rが1、すなわち、モノスルフィド結合を有する場合には、31.6〜32.2ppm付近に強いピークが存在する。本実施例においては、13C−NMR分析を行い、32.2ppm付近と38.8ppm付近のピーク強度から、それぞれモノスルフィド結合量とジスルフィド結合量を求めて、平均の硫黄含量を定量した。13C−NMR分析は、日本電子(株)製400MHzNMR装置を用い、溶媒にはCDCl3を用いた。
JIS A 1415 WS−Aに従ってサンシャインウェザーメーター(Sunshine Weather Meter)(S.W.O.M.)で曝露し、500時間後、1000時間後、1500時間後、2000時間後の硬化物の表面状態を観察した。評価基準は以下のとおりで、○であれば良好と判断した。
○: クラッキングがない
×: クラッキングがある 。
2mm厚シートを6枚重ねた硬化型組成物を30%圧縮した状態で固定して90℃で24時間養生し、次いで圧縮を開放してから23℃で24時間養生したものについて、厚みを測定し、加熱圧縮に対する復元率を次式により
復元率(%)=(復元時厚み−圧縮時の厚み)/(初期厚み−圧縮時の厚み)×100
求めた。
直径約120mm×2mm厚のシート状硬化物から、JIS K6251記載のダンベル状5号形に調整した打ち抜き刃を用いてダンベル試験片3本を切り出した。切り出したダンベル試験片に20mmの標線を付け、オリエンテック製テンシロンRTA−500を用いて、500mm/分で引張り試験を行った。ダンベル引張り測定における、M100(N/mm2)は100%伸長時(標線が40mmになった時点)の応力、Tmax(N/mm2)は最大引張応力、Emax(%)は最大荷重時の伸び率である。試験数は1検体n=3とし、平均値を測定結果とした。
直径約110mm×2mm厚のシート状硬化物から、ダンベル試験片3本を切り出し、残りのシートを4枚重ね、約50mm×約50mm×8mm厚のブロック状硬化物に調整した。この8mm厚のブロック状に調整した硬化物を23℃の雰囲気下にてJIS K6253記載のタイプAデュロメータにて硬度測定を行った。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、572.6gの42%水硫化ナトリウム水溶液、644gの水、78.3gの硫黄、254.6gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、568.9gの42%水硫化ナトリウム水溶液、650gの水、49.4gの硫黄、257.2gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、563.7gの42%水硫化ナトリウム水溶液、659gの水、10.0gの硫黄、260.5gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、562.4gの42%水硫化ナトリウム水溶液、661gの水、261.4gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、528.6gの42%水硫化ナトリウム水溶液、718gの水、87.4gの硫黄、284.0gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、526.8gの42%水硫化ナトリウム水溶液、721gの水、54.9gの硫黄、285.1gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、525.7gの42%水硫化ナトリウム水溶液、723gの水、33.0gの硫黄、285.9gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、629.2gのビス(2−クロロエチル)ホルマール、10.8gの1,2,3−トリクロロプロパン、12.2gのテトラブチルアンモニウムブロマイド50wt%水溶液、524.5gの42%水硫化ナトリウム水溶液、725gの水、11.0gの硫黄、286.7gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、640.0gのビス(2−クロロエチル)ホルマール、12.1gのテトラブチルアンモニウムブロマイド50wt%水溶液、514.2gの42%水硫化ナトリウム水溶液、565gの水、11.1gの硫黄、288.3gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
2Lのセパラブルフラスコを用いて、640.0gのビス(2−クロロエチル)ホルマール、12.1gのテトラブチルアンモニウムブロマイド50wt%水溶液、589.4gの42%水硫化ナトリウム水溶液、482gの水、9.5gの硫黄、246.5gの48%水酸化ナトリウム水溶液を反応させて、固体ポリサルファイドを経由させずに、淡黄色透明液体ポリマーを得た。得られたポリマーの硫黄の繰り返し数rの平均値、SH含量、粘度、比重、ガラス転移温度、50%重量減少温度を表1に示す。
実施例1〜3(No.2〜4)のポリマー100重量部に対し、二酸化マンガン(ハニウェル社製 TYPE−FA)18重量部と、添加剤として、SRFカーボン35重量部、フタル酸ブチルベンジル18重量部、テトラブチルチウラムジスルフィド0.9重量部(大内新興化学工業製 ノクセラーTBT)を加え、三本ロールミルを用いて混練した。トータル38gの混合物を2mmの隙間ができるように調整した鉄板で挟み込み、70℃で2時間加熱養生して、2mm厚のシート状硬化組成物を作製した。得られたシートを23℃50%RHの雰囲下に1時間放置して除熱した。約20mm角に切り出した硬化物の比重、ガラス転移温度、50%重量減少温度、復元率、硬度、ダンベル物性値を求めた。比重を表2に、その他の物性を表3に示す。
実施例10〜12と同様にして、ポリマーとしてNo.1(東レ・ファインケミカル製チオコール「LP−3」と「LP−23」を6:4の比率でブレンドしたポリマー)を用いて硬化型組成物を作製し、比重を測定した結果を表2に示す。さらに、2mm厚のシート状硬化物のガラス転移温度、50%重量減少温度、復元率、硬度、ダンベル物性値を求めた。得られた結果を表3に示す。
実施例4〜7(No.7〜10)のポリマー100重量部に対し、二酸化マンガン(ハニウェル社製 TYPE−FA)9重量部と、添加剤として、SRFカーボン35重量部、フタル酸ブチルベンジル9重量部、テトラブチルチウラムジスルフィド0.45重量部(大内新興化学工業製 ノクセラーTBT)を加え、三本ロールミルを用いて混練した。トータル34gの混合物を2mmの隙間ができるように調整した鉄板で挟み込み、70℃で2時間加熱養生して、2mm厚のシート状硬化組成物を作製した。得られたシートを23℃50%RHの雰囲下に1時間放置して除熱した。約20mm角に切り出した硬化物の比重を測定した。その結果を表2に示す。
実施例13〜16と同様にして、ポリマーとしてNo.6(東レ・ファインケミカル製チオコール「LP−3」と「LP−2」を1:9の比率でブレンドしたポリマー)を用いて硬化型組成物を作製し、比重を測定した結果を表2に示す。
実施例10〜12と同様にして、ポリマーとしてNo.5(比較例2のポリマー)を用いて2mm厚のシート状硬化型組成物を作製し、ガラス転移温度、50%重量減少温度、復元率、硬度、ダンベル物性値を求めた。得られた結果を表3に示す。
実施例3のポリマー(No.4、rの平均値が1.1)100重量部に対して、表4に示す配合剤を添加してプラネタリーミキサーを用いて主剤を作製し、さらにヘキサメチレンジイソシアネート(旭化成製デュラネート50M−HDI、NCO含量5.0%)134重量部を加えて手練りでよく混錬した。混合物をアルミ板上に50mm×12mm×3mm厚のシート状に成型し23℃で3日、次いで50℃で3日間養生して硬化物を得た。得られた硬化物をS.W.O.M.を用いて促進耐候性評価を行った。得られた結果を表4に示す。
実施例17と同様にして、比較例2のポリマー(No.5、rの平均値が1.0)を用いた3mm厚の硬化物を作製し、S.W.O.M.を用いて促進耐候性評価を行った。得られた結果を表4に示す。
実施例3のポリマー(No.4、rの平均値が1.1)100重量部に対して、ジャパンエポキシレジン製エポキシ樹脂「エピコート828」100重量部とアデカ製芳香族3級アミン「アデカハードナーEHC30」5重量部を手練りでよく混練した後に23℃で7日間養生して1cm厚の試験片を作製した。得られた硬化型組成物のガラス転移温度と50%重量減少温度を測定した。得られた結果を表5に示す。
実施例18と同様にして、実施例3のポリマーの代わりにサンプル1(東レ・ファインケミカル製チオコール「LP−3」と「LP−23」を6:4の比率でブレンドしたポリマー)を用いて硬化型組成物を作製し、ガラス転移温度と50%重量減少温度を測定した。得られた結果を表5に示す。
Claims (7)
- ガラス転移温度が−85℃以上−50℃以下である請求項1に記載のチオール基含有ポリマー。
- 50%重量減少温度が300℃以上350℃以下である請求項1に記載のチオール基含有ポリマー。
- 23℃における比重が1.18から1.28である請求項1に記載のチオール基含有ポリマー
- 請求項1から4のいずれかに記載のチオール基含有ポリマーと酸化剤を含有する硬化型組成物。
- 請求項1から4のいずれかに記載のチオール基含有ポリマーと分子中に2個以上のイソシアネート基含有化合物を含有する硬化型組成物。
- 請求項1から4のいずれかに記載のチオール基含有ポリマーと分子中に2個以上のグリシジル基を含有するエポキシ樹脂とアミン類を含有する硬化型組成物。
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TW201412826A (zh) | 2014-04-01 |
RU2617686C2 (ru) | 2017-04-26 |
WO2014021067A1 (ja) | 2014-02-06 |
KR20160093102A (ko) | 2016-08-05 |
US9663619B2 (en) | 2017-05-30 |
RU2017112503A (ru) | 2019-01-25 |
KR101743098B1 (ko) | 2017-06-02 |
KR20150037744A (ko) | 2015-04-08 |
US9738758B2 (en) | 2017-08-22 |
US20150307664A1 (en) | 2015-10-29 |
TWI518113B (zh) | 2016-01-21 |
CN104411747B (zh) | 2017-09-22 |
CN106832285A (zh) | 2017-06-13 |
US10179766B2 (en) | 2019-01-15 |
US20170226055A1 (en) | 2017-08-10 |
CN104411747A (zh) | 2015-03-11 |
CN106832285B (zh) | 2019-04-19 |
US20170009019A1 (en) | 2017-01-12 |
EP2881418A1 (en) | 2015-06-10 |
EP2881418A4 (en) | 2016-04-27 |
EP2881418B1 (en) | 2023-04-12 |
JPWO2014021067A1 (ja) | 2016-07-21 |
RU2015106941A (ru) | 2016-09-20 |
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