JP5922582B2 - コンポジット組成物 - Google Patents
コンポジット組成物 Download PDFInfo
- Publication number
- JP5922582B2 JP5922582B2 JP2012542033A JP2012542033A JP5922582B2 JP 5922582 B2 JP5922582 B2 JP 5922582B2 JP 2012542033 A JP2012542033 A JP 2012542033A JP 2012542033 A JP2012542033 A JP 2012542033A JP 5922582 B2 JP5922582 B2 JP 5922582B2
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- JP
- Japan
- Prior art keywords
- resin
- substituted
- composition
- group
- thermosetting resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 140
- 239000002131 composite material Substances 0.000 title claims description 41
- 229920005989 resin Polymers 0.000 claims description 149
- 239000011347 resin Substances 0.000 claims description 149
- 229920001187 thermosetting polymer Polymers 0.000 claims description 118
- 229920000647 polyepoxide Polymers 0.000 claims description 112
- 239000003822 epoxy resin Substances 0.000 claims description 111
- 239000003054 catalyst Substances 0.000 claims description 43
- 239000011342 resin composition Substances 0.000 claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 239000000835 fiber Substances 0.000 claims description 36
- 230000002787 reinforcement Effects 0.000 claims description 27
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 26
- 239000000945 filler Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000003063 flame retardant Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 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 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000012779 reinforcing material Substances 0.000 claims description 8
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 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 102
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 72
- 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 45
- 229930185605 Bisphenol Natural products 0.000 description 39
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
- 229940106691 bisphenol a Drugs 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- 229920003986 novolac Polymers 0.000 description 27
- -1 aryl glycidyl ethers Chemical class 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000654 additive Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 229910052794 bromium Inorganic materials 0.000 description 17
- 239000011521 glass Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 16
- 239000004593 Epoxy Substances 0.000 description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 16
- 239000011574 phosphorus Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 238000000113 differential scanning calorimetry Methods 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000009477 glass transition Effects 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000005022 packaging material Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000002118 epoxides Chemical group 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000004634 thermosetting polymer Substances 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- 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 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 229910010271 silicon carbide Inorganic materials 0.000 description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
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- 229920000642 polymer Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- RJWLXGOSIRVRAR-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C(C)=C1O RJWLXGOSIRVRAR-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- OLJXRTRRJSMURJ-UHFFFAOYSA-N 4-amino-2-methoxybenzoic acid Chemical compound COC1=CC(N)=CC=C1C(O)=O OLJXRTRRJSMURJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZVIDMSBTYRSMAR-UHFFFAOYSA-N N-Methyl-4-aminobenzoate Chemical compound CNC1=CC=C(C(O)=O)C=C1 ZVIDMSBTYRSMAR-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 239000012963 UV stabilizer Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229910001593 boehmite Inorganic materials 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
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- SXOZDDAFVJANJP-UHFFFAOYSA-N cyclodecanone Chemical compound O=C1CCCCCCCCC1 SXOZDDAFVJANJP-UHFFFAOYSA-N 0.000 description 2
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- NPEJHLDODKUWCF-UHFFFAOYSA-N cycloicosanone Chemical compound O=C1CCCCCCCCCCCCCCCCCCC1 NPEJHLDODKUWCF-UHFFFAOYSA-N 0.000 description 2
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
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- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
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- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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- 125000005592 polycycloalkyl group Polymers 0.000 description 2
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- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
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- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
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- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WSNJABVSHLCCOX-UHFFFAOYSA-J trilithium;trimagnesium;trisodium;dioxido(oxo)silane;tetrafluoride Chemical compound [Li+].[Li+].[Li+].[F-].[F-].[F-].[F-].[Na+].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O WSNJABVSHLCCOX-UHFFFAOYSA-J 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
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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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/092—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising epoxy resins
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/04—Layered products comprising a layer of synthetic resin as impregnant, bonding, or embedding substance
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
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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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
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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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
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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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
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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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
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Description
(1)低い架橋密度を有し、従って比較的強靱である二官能性樹脂をベースにして、改良された機械的特性、例えば改良された靱性;
(2)改良された熱特性、例えばジシアンジアミドによって硬化させたとき、約150℃よりも高い、好ましくは約170℃よりも高い、更に好ましくは約190℃よりも高い、より高いガラス転移温度;
(3)より高い耐湿特性(高い防湿性又は換言すると、低い水吸収);
(4)より低い誘電定数/誘電正接(Dk/Df)特性及び
(5)約150mPa-sよりも低い、好ましくは約120mPa-sよりも低い低粘度を示すエポキシ樹脂をベースにする、
を有する。
ビスフェノールシクロドデカノンとD.E.R.(登録商標)330とのアドバンスト反応
ビスフェノールシクロドデカノンの66.8グラム(g)サンプル(189.8ミリモル)を、500mLのガラス反応器内で、133.1gのD.E.R.(登録商標)330(371.8ミリモル)中に、140℃で溶解させて、混合物を形成させた。この混合物を80℃まで冷却し、次いで100mgのAl触媒溶液(メタノール中70%固体)をこの混合物に添加し、ビスフェノールシクロドデカノンとD.E.R.(登録商標)330との反応を開始させた。アドバンスト反応を150℃で実施して、アドバンスト樹脂Aを形成させた。1時間後に、このアドバンスト樹脂Aを、滴定によってキャラクタリゼーションした。滴定から得られたアドバンスト樹脂AのEEWは、520g/eq(EEW理論=551g/eq)であった。アドバンスト樹脂AのTgは、10℃/分の加熱勾配でDSCによって測定した。Tgは54℃であった。
ビスフェノールAの52.5gサンプル(230.3ミリモル)を、500mLのガラス反応器内で、147.4gのD.E.R.(登録商標)330(411.7ミリモル)中に、140℃で溶解させた。この混合物を80℃まで冷却し、次いで100mgのAl触媒溶液(メタノール中70%固体)をこの混合物に添加し、ビスフェノールAとD.E.R.(登録商標)330とのアドバンスメント反応を開始させた。この反応を150℃で実施して、比較アドバンスト樹脂Aを形成させた。1時間後に、この比較アドバンスト樹脂Aを、滴定によってキャラクタリゼーションした。滴定から得られた比較アドバンスト樹脂AのEEWは、569g/eq(EEW理論=552g/eq)であった。比較アドバンスト樹脂AのTgは、10℃/分の加熱勾配でDSCによって測定した。Tgは49℃であった。
ビスフェノールシクロドデカノンとD.E.R.(登録商標)330とのアドバンスト樹脂の硬化
上記実施例1から得られたアドバンスト樹脂A(EEW=520g/eq)の20.0gサンプルを、0.48gのdicy及び0.25gのEPON(登録商標)P101と混合した。この混合物を、200℃で2時間硬化させて、硬化樹脂Aを形成させた。硬化樹脂AのTgを、DSCによって10℃/分の加熱勾配で測定した。硬化樹脂AのTgは141℃であった。
上記比較例Aから得られたアドバンスト樹脂B(EEW=569g/eq)の20.0gサンプルを、0.45gのdicy(EEW=14g/eq)及び0.26gのEPON P101と混合した。
2種の樹脂(樹脂C及び比較樹脂C)の靱性を、DMAによって測定した。樹脂Cからなる実施例2の硬化樹脂は、実施例1における手順を使用して製造されたアドバンストビスフェノールシクロドデカノン樹脂である。樹脂Cを、実施例2における手順を使用してPlenco13943によって硬化させた。この硬化樹脂を本明細書において「硬化樹脂C」(実施例3)として参照する。
アドバンストビスフェノールシクロドデカノン樹脂から製造された積層板
パートA.D.E.R.(登録商標)330を含有するアドバンストビスフェノールシクロドデカノン
ビスフェノールシクロドデカノンの99.88gサンプル(0.57モル)を、500mLのガラス反応器内で、399.88gのD.E.R.(登録商標)330(2.22モル)中に、140℃で溶解させて、混合物を形成させた。この混合物を80℃まで冷却し、次いで231mgのAl触媒溶液(メタノール中70%固体)をこの混合物に添加した。Al触媒溶液を含有する得られる混合物を、約150℃まで加熱した。ビスフェノールシクロドデカノンとD.E.R.(登録商標)330とのアドバンスト反応を150℃で約1時間実施して、アドバンスト樹脂Eを形成させた。
47重量%の上記パートAで製造した樹脂F(溶媒無しで計算した、即ち、100%固体含有量)を53重量%のstyle7628ガラスクロス(Porcher731仕上)の上にコーティングすることによって、プリプレグを製造した。樹脂F中の溶媒(Dowanol(登録商標)PM)を、温度を約165℃に設定したオーブン内で、約5分間蒸発させて、プリプレグを形成させた。
臭素化したアドバンストビスフェノールシクロドデカノン樹脂
150g(100%固体含有量基準)のビスフェノールシクロドデカノン、150gのD.E.R.(登録商標)560(58.8%のBrで100%固体含有量基準)及び200gのDowanol(登録商標)PM溶媒を、反応器の中に装入した。この混合物を60℃まで加温して、ビスフェノールシクロドデカノン及びD.E.R.(登録商標)560をDowanol(登録商標)PM溶媒中に溶解させた。次いで、この混合物を、この混合物に添加した0.643グラムのAl触媒溶液(メタノール中70%固体)と共に、100℃まで加熱した。この混合物を、Dowanol(登録商標)PM溶媒が還流で沸騰し始める(137℃)まで連続的に加熱した。ビスフェノールシクロドデカノンとD.E.R.(登録商標)560とのアドバンスト反応を、137℃で約150分間行って、臭素化アドバンスト樹脂Gを形成させた。臭素化アドバンスト樹脂Gを、室温にまで冷却させた。
エポキシ化ビスフェノールシクロドデカノン(ビスフェノールシクロドデカノン変性エポキシ樹脂)の形成
下記の手順に従って、ビスフェノールシクロドデカノンをエピクロロヒドリンと、7.5:1の比(エピクロロヒドリン対ヒドロキシル(−OH)当量)で反応させることによって、ビスフェノールシクロドデカノンのエポキシ化を行った。
エポキシ化ビスフェノールシクロドデカノンとTBBAとのアドバンスト反応によって形成されたアドバンスト臭素化エポキシ樹脂
上記実施例6から得られたエポキシ化ビスフェノールシクロドデカノン生成物(EEW 236g/eq)の7.63gサンプル及び4.52gのTBBA(EEW 272g/eq、Br58.8%)を、ホットプレート上のアルミニウムカップ内で溶融させて、均一混合物を得た。約0.0049gのAl触媒を、この均一混合物に添加した。エポキシ化ビスフェノールシクロドデカノン生成物とTBBAとのアドバンスト反応を、120℃で1時間行って、アドバンスト樹脂を形成させた。次いで、このアドバンスト樹脂を2.98gのアセトン(アセトン中80%固体)中にdicyと共に溶解させて、樹脂混合物を形成させた。この樹脂混合物をホットプレート上で170℃で10分間及び190℃で90分間硬化させて、アドバンスト臭素化エポキシ樹脂生成物を形成させた。
パートA.プリプレグ手順
ガラスウェブ(Porcherスタイル Nr.7628/36アミンシラン仕上)にワニス混合物を含浸させることによって、プリプレグを製造した。一方のワニス混合物(実施例8)は、実施例7のアドバンスト臭素化樹脂から製造し、他方のワニス混合物(比較例D)は、TBBAでアドバンスした従来のエポキシ化ビスフェノールAから製造した。プリプレグは、長さが3メートルのCaratschパイロットトリーターを使用して形成した。「ハンドレイアップ」は、ワニスをガラスウェブの上に注ぐことによって製造した。ワニスをガラスウェブ全体に広げ、その後、ガラスウェブをトリーターローラーに通過させた。次いで、樹脂含浸ウェブをトリーターに通過させ、175〜180℃の温度で加熱して、得られるプリプレグを形成させた。
上記パートAからのプリプレグ8層並びに頂及び底に銅箔を使用して、積層板を製造した。8層を20N/cm2で、3°K/分の加熱勾配で室温から190℃までプレスし、そして90分間保持した。
エポキシ化ビスフェノールシクロドデカノンの合成
サーモスタット制御加熱マントルを取り付けた2リットルの三つ口丸底ガラス反応器に、ビスフェノールシクロドデカノン(約176g、1.0ヒドロキシル当量)、エピクロロヒドリン(約694g、7.5モル)及びイソプロパノール(約373g、使用したエピクロロヒドリンの35重量%)を装入した。この反応器に、更に、凝縮器(−15℃に維持)、温度計、クライゼンアダプター、オーバーヘッド窒素入口(1LPM N2を使用)及び攪拌機アセンブリ(テフロン(登録商標)パドル、ガラス軸、可変速モーター)を取り付けた。50℃で溶解した後、水酸化ナトリウムの溶液(水中20%、180g)を、サイドアーム排気添加漏斗から、20〜30分間かけて添加した。攪拌を開始して、エピクロロヒドリン及びイソプロパノール中のビスフェノールシクロドデカノンのスラリーを得た。この反応の間、温度を50℃で維持した。20分間の後反応の後に、攪拌を停止し、水層を有機層から除去した。
dicyによるeCDONの硬化
eCDONのサンプル(4.62g)、dicy(0.34g)及び2−フェニルイミダゾール(0.038g)を、極低温粉砕によって混合した。この手順には、固体を、ねじ込み末端を有するステンレススチールシリンダーに添加すること、金属球を添加すること、内容物を液体窒素中で冷却すること及びアセンブリーを10分間振盪することが含まれる。このシリンダーを窒素パージバッグの中に入れ、室温にまで暖めた。この粉末の一部をアルミニウムパンの中に入れ、真空オーブン内で190℃で90分間加熱して、透明な注型品を形成させた。DSCによって、202℃のTgが観察された。この注型品を、4個の片に切断し、それぞれを秤量し、全部を、スチームオートクレーブの中に121℃で90分間置いた。それぞれの片の重量増分を、パーセントで表し、4個の値を平均して、2.3重量%の値を得た。
dicyによるD.E.R.(登録商標)331の硬化
D.E.R.(登録商標)331(ビスフェノールAジグリシジルエーテル、4.51g)、dicy(0.44g)及び2−フェニルイミダゾール(0.05g)を使用して、実施例10に記載された実験を繰り返した。DSCによって139℃のTgが観察され、水吸収は3.9重量%であった。
以下に、本発明の関連態様を記載する。
態様1.(I)少なくとも1種の熱硬化性樹脂組成物、(II)少なくとも1種の硬化剤及び(III)少なくとも1種の強化材を含んでなり、Tgが少なくとも約150℃であり、150℃で200mPa-sよりも低い粘度を有する二官能性エポキシ樹脂から製造され、エポキシ当量重量が190g/当量よりも大きい、コンポジット及び電気用積層板用硬化性樹脂組成物。
態様2.前記強化材が高強度フィラメント又は繊維を含んでなる態様1に記載の組成物。
態様3.前記熱硬化性樹脂組成物が下記一般式I:
によって表されるエポキシ樹脂を含んでなる態様1に記載の組成物。
態様4.前記熱硬化性樹脂組成物が下記一般式II:
によって表されるアドバンストエポキシ樹脂組成物を含んでなる態様1に記載の組成物。
態様5.前記熱硬化性樹脂組成物が下記一般式III:
によって表されるアドバンスト活性水素官能性樹脂組成物を含んでなる態様1に記載の組成物。
態様6.成分(I)とは異なる少なくとも1種の熱硬化性樹脂がエポキシ樹脂、イソシアネート樹脂、(メタ)アクリル樹脂、フェノール樹脂、ビニル樹脂、スチレン系樹脂、ポリエステル樹脂及びこれらの混合物から選択される樹脂を含んでなる態様1に記載の組成物。
態様7.少なくとも1種の熱硬化性樹脂成分(I)の濃度が、組成物の合計重量基準で、約10重量%〜約99重量%の熱硬化性樹脂を含んでなる態様1に記載の組成物。
態様8.(IV)式Iとは異なるエポキシ樹脂、(V)充填剤、(VI)難燃剤、(VII)触媒及び(VIII)溶媒の少なくとも1種を更に含む態様1に記載の組成物。
態様9.成分(I)の少なくとも1種の熱硬化性樹脂がジヒドロキシジフェニル−シクロアルカン化合物のジグリシジルエーテルを含んでなり、前記ジヒドロキシジフェニル−シクロアルカン化合物が下記一般式IV:
によって表されるジヒドロキシジフェニル−シクロアルカン化合物を含んでなる態様1に記載の組成物。
態様10.前記ジヒドロキシジフェニル−シクロアルカン化合物が約C8〜約C20の炭素原子を含有するシクロアルカン化合物から作られる態様1に記載の組成物。
態様11.前記シクロアルカン化合物がシクロオクタノン、シクロデカノン、シクロドデカノン、シクロペンタデカノン、シクロオクタデカノン、シクロエイコサノン及びこれらの混合物を含む態様11に記載の組成物。
態様12.シクロアルカン化合物がビスフェノールシクロドデカノンを含む態様12に記載の組成物。
態様13.成分(I)が、組成物の合計重量基準で、約20重量%〜約98重量%を含み、成分(II)が、組成物の合計重量基準で、約2重量%〜約50重量%を含む態様1に記載の組成物。
態様14.態様1に記載の組成物から製造されたコンポジット又は積層板物品。
態様15.前記物品がプリント回路基板、電気用若しくは電子用注型品、電気用若しくは電子用注封品、電気用若しくは電子用カプセル品又は電気用積層板である態様14に記載の物品。
Claims (7)
- (I)少なくとも1種の熱硬化性樹脂、(II)ジシアンジアミドを含む少なくとも1種の硬化剤及び(III)少なくとも1種の強化材を含んでなる熱硬化性樹脂組成物であって、前記熱硬化性樹脂組成物が少なくとも150℃のTgを有するコンポジット又は電気用積層板を形成でき、そして、150℃で200mPa-sよりも低い粘度を有する、コンポジット及び電気用積層板用硬化性樹脂組成物であって、前記少なくとも1種の熱硬化性樹脂(I)が下記一般式I:
によって表されるエポキシ樹脂を含む組成物。 - 前記強化材が高強度フィラメント又は繊維を含んでなる請求項1に記載の組成物。
- 前記熱硬化性樹脂成分(I)が一般式Iで表わされるエポキシ樹脂とは異なるエポキシ樹脂を更に含む請求項1に記載の組成物。
- 少なくとも1種の熱硬化性樹脂成分(I)の濃度が、組成物の合計重量基準で、10重量%〜99重量%の熱硬化性樹脂を含んでなる請求項1に記載の組成物。
- (IV)一般式Iとは異なるエポキシ樹脂、(V)充填剤、(VI)難燃剤、(VII)触媒及び(VIII)溶媒の少なくとも1種を更に含む請求項1に記載の組成物。
- 成分(I)の少なくとも1種の熱硬化性樹脂がジヒドロキシジフェニル−シクロアルカン化合物のジグリシジルエーテルを含んでなり、前記ジヒドロキシジフェニル−シクロアルカン化合物が下記一般式IV:
によって表されるジヒドロキシジフェニル−シクロアルカン化合物を含んでなる請求項1に記載の組成物。
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PCT/US2010/056101 WO2011068643A2 (en) | 2009-12-02 | 2010-11-10 | Composite compositions |
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CN (1) | CN102666638B (ja) |
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-
2010
- 2010-11-10 KR KR1020127016915A patent/KR20120116424A/ko active IP Right Grant
- 2010-11-10 WO PCT/US2010/056101 patent/WO2011068643A2/en active Application Filing
- 2010-11-10 US US13/513,205 patent/US9006312B2/en not_active Expired - Fee Related
- 2010-11-10 SG SG2012040721A patent/SG181485A1/en unknown
- 2010-11-10 JP JP2012542033A patent/JP5922582B2/ja active Active
- 2010-11-10 EP EP10779884A patent/EP2507285A2/en not_active Withdrawn
- 2010-11-10 CN CN201080054818.1A patent/CN102666638B/zh not_active Expired - Fee Related
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TW201139491A (en) | 2011-11-16 |
KR20120116424A (ko) | 2012-10-22 |
SG181485A1 (en) | 2012-07-30 |
US9006312B2 (en) | 2015-04-14 |
WO2011068643A2 (en) | 2011-06-09 |
WO2011068643A3 (en) | 2011-08-18 |
CN102666638A (zh) | 2012-09-12 |
CN102666638B (zh) | 2015-01-14 |
US20120289624A1 (en) | 2012-11-15 |
EP2507285A2 (en) | 2012-10-10 |
JP2013512987A (ja) | 2013-04-18 |
TWI529190B (zh) | 2016-04-11 |
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