TWI820016B - 纖維強化塑膠用樹脂組合物、其硬化物、及包含該硬化物之纖維強化塑膠 - Google Patents
纖維強化塑膠用樹脂組合物、其硬化物、及包含該硬化物之纖維強化塑膠 Download PDFInfo
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- TWI820016B TWI820016B TW107106448A TW107106448A TWI820016B TW I820016 B TWI820016 B TW I820016B TW 107106448 A TW107106448 A TW 107106448A TW 107106448 A TW107106448 A TW 107106448A TW I820016 B TWI820016 B TW I820016B
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- Prior art keywords
- fiber
- cyanate ester
- epoxy resin
- resin composition
- groups
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 58
- 229920002430 Fibre-reinforced plastic Polymers 0.000 title claims abstract description 53
- 239000011151 fibre-reinforced plastic Substances 0.000 title claims abstract description 53
- 239000004643 cyanate ester Substances 0.000 claims abstract description 73
- 239000003822 epoxy resin Substances 0.000 claims abstract description 72
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 21
- 125000004185 ester group Chemical group 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 16
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 10
- 239000012783 reinforcing fiber Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
- 238000005452 bending Methods 0.000 abstract description 8
- 239000004566 building material Substances 0.000 abstract description 2
- 238000010248 power generation Methods 0.000 abstract description 2
- -1 aliphatic amines Chemical class 0.000 description 41
- 239000000835 fiber Substances 0.000 description 23
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 238000000465 moulding Methods 0.000 description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 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 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 235000013824 polyphenols Nutrition 0.000 description 6
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical class O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 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 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000001721 transfer moulding Methods 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- GKRHRWMLLPMCST-UHFFFAOYSA-N 4-[1-(4-cyanophenyl)ethyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(C)C1=CC=C(C#N)C=C1 GKRHRWMLLPMCST-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- 150000001913 cyanates Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000009719 polyimide resin Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- PBUMTLOEAITQSM-UHFFFAOYSA-N 2-(3-aminopentan-3-yl)aniline Chemical compound CCC(N)(CC)C1=CC=CC=C1N PBUMTLOEAITQSM-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- IWRZKNMUSBNOOD-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C=1C=C(N(CC2OC2)CC2OC2)C(C)=CC=1OCC1CO1 IWRZKNMUSBNOOD-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- CSKRBHOAJUMOKJ-UHFFFAOYSA-N 3,4-diacetylhexane-2,5-dione Chemical compound CC(=O)C(C(C)=O)C(C(C)=O)C(C)=O CSKRBHOAJUMOKJ-UHFFFAOYSA-N 0.000 description 2
- WDULIZRNXLCPBC-UHFFFAOYSA-N 3-(2-phenylpropan-2-yl)benzene-1,2-diamine Chemical compound C=1C=CC(N)=C(N)C=1C(C)(C)C1=CC=CC=C1 WDULIZRNXLCPBC-UHFFFAOYSA-N 0.000 description 2
- FBFIDNKZBQMMEQ-UHFFFAOYSA-N 3-(3-phenylpentan-3-yl)benzene-1,2-diamine Chemical compound C=1C=CC(N)=C(N)C=1C(CC)(CC)C1=CC=CC=C1 FBFIDNKZBQMMEQ-UHFFFAOYSA-N 0.000 description 2
- XWULMVRLWXONCN-UHFFFAOYSA-N 4-[2-(4-cyanophenyl)propan-2-yl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(C)(C)C1=CC=C(C#N)C=C1 XWULMVRLWXONCN-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical group NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- IYFFMJRSFTZNIC-UHFFFAOYSA-N trihydroxy-di(tridecyl)-$l^{5}-phosphane Chemical compound CCCCCCCCCCCCCP(O)(O)(O)CCCCCCCCCCCCC IYFFMJRSFTZNIC-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
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- WAHBMPYCNRZYBV-UHFFFAOYSA-N (3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl 2-methylcyclohexane-1-carboxylate Chemical compound CC1CCCCC1C(=O)OCC1C(C)CC2OC2C1 WAHBMPYCNRZYBV-UHFFFAOYSA-N 0.000 description 1
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 1
- WUOACPNHFRMFPN-VIFPVBQESA-N (R)-(+)-alpha-terpineol Chemical compound CC1=CC[C@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-VIFPVBQESA-N 0.000 description 1
- QRFMXBKGNQEADL-UHFFFAOYSA-N 1,1'-biphenyl;phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=CC=C1C1=CC=CC=C1 QRFMXBKGNQEADL-UHFFFAOYSA-N 0.000 description 1
- OBPQOFOPKSWFPC-UHFFFAOYSA-N 1,2,3-tridodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC(CCCCCCCCCCCC)=C1CCCCCCCCCCCC OBPQOFOPKSWFPC-UHFFFAOYSA-N 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
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Abstract
本發明係一種纖維強化塑膠用樹脂組合物,其含有(A)氰酸酯、(B)環氧樹脂、及(C)於25℃下為液狀之芳香族胺系硬化劑,且(A)氰酸酯之平均氰酸酯基數為2.1以上,及/或(B)環氧樹脂之平均環氧基數為2.1以上;使用該組合物及強化纖維而製造之纖維強化塑膠,除耐熱性良好以外,拉伸或彎曲物性亦優異,故而可應用於船舶、汽車、飛機等運輸機;運動用品、洗面台、窗框等建築材料;高壓氣體鋼瓶、風力發電用葉片等工業機件等廣泛之領域。
Description
本發明係關於一種纖維強化塑膠用樹脂組合物,更詳細而言,係關於一種纖維強化塑膠用樹脂組合物、及含有該組合物之硬化物之纖維強化塑膠,該纖維強化塑膠用樹脂組合物調整氰酸酯之氰酸酯基數及環氧樹脂之環氧基數,而使玻璃轉移點溫度(Tg)與應用於纖維強化塑膠時之強度之平衡性良好。
針對碳纖維或玻璃纖維等纖維材料,使用熱硬化性之環氧樹脂、或不飽和聚酯、聚醯胺樹脂、或酚樹脂作為補強材料而製作成型物之方法眾所周知。使用該方法之纖維強化塑膠廣泛使用於飛機、船舶等結構體之材料,或網球拍、高爾夫球桿等運動用品。由於環氧樹脂不僅接著性、耐熱性、耐化學品性優異,而且廉價,故而作為平衡性良好之材料而多用於補強材料。 環氧樹脂組合物具有優異之電氣性能及接著力,而於環氧樹脂中進而混合氰酸酯之情形時,於硬化時藉由形成三𠯤環而可獲得剛性且高耐熱性之硬化物,故而多用於半導體之密封材料、或者電子電路基板等之成形用途。 於專利文獻1中,記載有藉由於環氧樹脂、氰酸酯中添加聚醯亞胺樹脂,製造薄膜之預浸體,並將該預浸體積層而提供電特性或耐熱性良好之銅箔積層板。於引用文獻1中所記載之發明中,利用聚醯亞胺樹脂達成高耐熱性之樹脂組合物,但於將本發明應用於纖維強化塑膠用之情形時,存在以下問題:由於聚醯亞胺為固體,故而若不使用溶劑,則使用較為困難,以及於使用溶劑之情形時亦必須經過乾燥步驟等,於作業性方面產生問題。又,於不使用聚醯亞胺樹脂之情形時,於耐熱性或各種物性方面存在問題。 於專利文獻2中,記載有提供使用具有聯苯骨架之多官能氰酸酯之預浸體、及積層板。引用文獻2中所記載之積層板或印刷配線基板具有高耐熱、低介電特性。然而,於為了製造纖維強化塑膠而利用引用文獻2中所記載之發明之情形時,硬化物對纖維之追隨性較差,於測定拉伸或彎曲等各種物性之情形時,存在可見纖維與樹脂組合物間之剝離等,結果無法獲得令人滿意之纖維強化塑膠之問題。 通常,於使用氰酸酯及環氧樹脂之硬化體系中,氰酸酯與具有活性氫之硬化劑作用,成為活性種之後,該活性種與環氧樹脂反應,進行高分子量化。於氰酸酯之氰酸酯基數或環氧樹脂之環氧基數過少之情形時,反應點較少而難以進行高分子量化,無法獲得令人滿意之硬化物。 進而,於使用氰酸酯及環氧樹脂之硬化體系中,於所使用之硬化劑中亦有必要選擇適當者。例如,如間苯二甲胺或異佛爾酮二胺等脂肪族胺之反應性較高之硬化劑中,於應用於纖維強化塑膠用之情形時使用壽命較短,含浸於纖維之前樹脂組合物即硬化,無法獲得均勻之纖維強化塑膠。又,如專利文獻3,於使用常溫下為固體之潛伏性硬化劑之情形時,存在以下問題:雖然可確保使用壽命,但是由於硬化劑為固體,故而於欲應用於纖維強化塑膠之情形時,硬化劑難以自纖維之表面滲透,氰酸酯及環氧樹脂與硬化劑分離,硬化反應未適當地進行。 [先前技術文獻] [專利文獻] 專利文獻1:日本專利特開2001-294689號公報 專利文獻2:日本專利特開2010-174242號公報 專利文獻3:美國專利8911586號公報
因此,本發明所欲解決之問題在於提供一種樹脂組合物,其為高耐熱性,進而,於用於製造纖維強化塑膠之情形時,可獲得對纖維之追隨性優異,拉伸或彎曲等各種物性良好之纖維強化塑膠。 對此,為了解決上述問題,本發明者等人進行了銳意研究,發現一種樹脂組合物,其於使用氰酸酯、環氧樹脂之情形時,藉由控制體系內之平均氰酸酯基數、及平均環氧基數,使用於25℃下為液狀之芳香族胺作為硬化劑,可獲得耐熱性及各種物性之平衡性良好之硬化物,從而完成本發明。即,本發明係一種纖維強化塑膠用樹脂組合物,其含有(A)氰酸酯、(B)環氧樹脂、及(C)於25℃下為液狀之芳香族胺系硬化劑,且下述式(1)所表示之(A)氰酸酯之平均氰酸酯基數為2.1以上,及/或下述式(2)所表示之(B)環氧樹脂之平均環氧基數為2.1以上。 [數1](於式(1)中,n表示(A)氰酸酯中所包含之氰酸酯成分之種類數,Ai
表示(A)氰酸酯中所包含之第i種氰酸酯成分之氰酸酯基數,Xi
表示(A)氰酸酯中之第i種氰酸酯成分之質量基準之含有比率) [數2](於式(2)中,n表示(B)環氧樹脂中所包含之環氧樹脂成分之種類數,Bk
表示(B)環氧樹脂中所包含之第k種環氧樹脂成分之環氧基數,Yk
表示(B)環氧樹脂中之第k種環氧樹脂成分之質量基準之含有比率)
以下,對本發明之纖維強化塑膠用樹脂組合物之實施形態進行說明。 [(A)氰酸酯] 本發明中所使用之作為(A)成分之氰酸酯係分子中具有氰酸酯基之化合物。作為(A)成分之氰酸酯存在包含1種氰酸酯之情況,或者亦存在為複數種氰酸酯之混合物之情況。作為(A)成分之氰酸酯較佳為由下述式(1)表示時之(A)成分總體之平均氰酸酯基數為2.1以上。 [數3](於式(1)中,n表示(A)氰酸酯中所包含之氰酸酯成分之種類數,Ai
表示(A)氰酸酯中所包含之第i種氰酸酯成分之氰酸酯基數,Xi
表示(A)氰酸酯中之第i種氰酸酯成分之質量基準之含有比率) 關於上述式(1),例如,於(A)氰酸酯為含有3種氰酸酯之混合物之情形時,n為3。此時,3種氰酸酯分別表示為成分1、成分2、成分3,各成分之氰酸酯基數由A1
、A2
、A3
表示。又,成分A1
、A2
、A3
之質量基準之含有比率分別由X1
、X2
、X3
表示,此時之平均氰酸酯基數利用[(A1
×X1
)+(A2
×X2
)+(A3
×X3
)]/100進行計算。並且,本發明中所使用之(A)氰酸酯較佳為由上述式(1)所得之氰酸酯基數之值為2.1以上。 關於上述平均氰酸酯基數,自硬化物之Tg與纖維強化塑膠之可靠性之平衡性之觀點而言,較佳為2.1~5.0,更佳為2.2~5.0,進而較佳為2.4~4.1。於平均氰酸酯基數大於上述範圍之情形時,有樹脂組合物之黏度增高,無法使樹脂組合物全部量含浸於纖維中,纖維強化塑膠之成形變得困難之傾向。 於本發明中所使用之(A)氰酸酯包含1種氰酸酯之情形時,較佳為上述該氰酸酯之氰酸酯基數為上述範圍。又,於本發明之(A)氰酸酯為複數種氰酸酯之混合物之情形時,較佳為藉由調整混合物中之氰酸酯之調配量,使混合物之上述平均氰酸酯基數成為上述範圍。 作為本發明之(A)氰酸酯,例如,較佳為使用選自由下述通式(3-1)所表示之化合物、下述通式(3-1)所表示之化合物之預聚物、及下述通式(3-2)所表示之化合物所組成之群中之至少1種化合物及/或預聚物。 [化1](於通式(3-1)中,Ra
表示單鍵、-S-或2價烴基,Rb
及Rc
分別獨立地表示未經取代或經1~4個烷基取代之伸苯基, 於Rb
及Rc
經2~4個烷基取代之情形時,存在該烷基相同之情況,亦存在不同之情況) [化2](於通式(3-2)中,n表示1~10之整數,Rd
表示氫原子、或碳數為1~4之烷基) 作為通式(3-1)中之Ra
所表示之2價烴基,可列舉:碳原子數1~8之伸烷基、碳原子數3~13之伸環烷基、碳原子數6~12之伸芳基、伸芳基伸烷基、伸芳基二伸烷基等。 作為碳原子數1~8之伸烷基,可列舉:亞甲基、伸乙基、伸丙基、甲基伸乙基、伸丁基、1-甲基伸丙基、2-甲基伸丙基、1,2-二甲基伸丙基、1,3-二甲基伸丙基、1-甲基伸丁基、2-甲基伸丁基、3-甲基伸丁基、4-甲基伸丁基、2,4-二甲基伸丁基、1,3-二甲基伸丁基、伸戊基、伸己基、伸庚基、伸辛基、乙烷-1,1-二基、丙烷-2,2-二基等。 作為碳原子數3~13之伸環烷基,可列舉:1,2-伸環丙基、1,3-伸環庚基、反式-1,4-伸環己基等。 作為碳原子數6~12之伸芳基,可列舉:伸苯基、甲伸苯基、伸萘基等。 作為伸芳基伸烷基,可列舉:伸苯基亞甲基、伸苯基伸乙基等。 作為伸芳基二伸烷基,可列舉:伸苯基二亞甲基、伸苯基二伸乙基等。 關於上述碳原子數1~8之伸烷基及伸芳基伸烷基以及伸芳基二伸烷基中之亞甲基鏈,亦存在被-O-、-S-、-CO-或-C=C-取代之情況。 關於碳原子數1~8之伸烷基、碳原子數6~12之伸芳基、伸芳基伸烷基及伸芳基二伸烷基,存在經氰基、羧基、碳原子數1~4之烷基、羥基、碳原子數1~4之烷氧基或鹵素原子取代之情況。作為存在取代碳原子數1~8之伸烷基等之情況之碳原子數1~4之烷基,可列舉後述之碳數為1~4之烷基,作為碳原子數1~4之烷氧基,可列舉後述之碳數為1~4之烷基經氧原子中斷者。 作為通式(3-1)中之存在取代伸苯基之情況之Rb
及Rc
所表示之烷基,可列舉碳數1~8之烷基。作為碳數1~8之烷基,可列舉:甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第二戊基、第三戊基、己基、1-乙基戊基、環己基、1-甲基環己基、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基等。 作為通式(3-2)中之Rd
所表示之碳數為1~4之烷基,可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基等。 關於上述通式(3-1)所表示之化合物,自獲得之容易性等觀點而言,較佳為下述通式(3-3)所表示之化合物。 [化3](於通式(3-3)中,Re
表示單鍵、亞甲基、-CH(CH3
)-、-C(CH3
)2
-、或下述通式(4-1)~(4-8)所表示之任一官能基, Rf
、Rg
、Rh
、及Ri
分別獨立地表示氫原子、或碳數為1~4之烷基) [化4](於通式(4-3)中,m表示4~12之整數, 通式(4-1)~(4-8)中之*表示鍵結鍵) 作為通式(3-3)中之Rf
、Rg
、Rh
、及Ri
所表示之碳數為1~4之烷基,可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基等。 作為上述通式(3-3)所表示之化合物,例如可列舉:雙(4-氰酸基苯基)甲烷、雙(3,5-二甲基-4-氰酸基苯基)甲烷、1,1-雙(4-氰酸基苯基)乙烷、2,2-雙(4-氰酸基苯基)丙烷等。 關於本發明中所使用之(A)氰酸酯,自獲得之容易性及硬化物之耐熱性之觀點而言,尤佳為上述通式(3-2)所表示之化合物、1,1-雙(4-氰酸基苯基)乙烷、2,2-雙(4-氰酸基苯基)丙烷。 關於本發明之纖維強化塑膠用樹脂組合物中之(A)氰酸酯之含量,相對於後述之(B)環氧樹脂100質量份,較佳為10~200質量份,更佳為30~150質量份,進而較佳為50~120質量份。於(A)氰酸酯之含量少於10質量份之情形時,有樹脂組合物之強度不提高之傾向,於大於200質量份之情形時,有樹脂組合物對基材之密接性顯著下降之傾向。 [(B)環氧樹脂] 本發明中所使用之作為(B)成分之環氧樹脂係分子中具有環氧基之化合物。作為(B)成分之環氧樹脂存在包含1種環氧樹脂之情況,或者亦存在為複數種環氧樹脂之混合物之情況。作為(B)成分之環氧樹脂較佳為下述式(2)所表示之(B)成分總體之平均環氧基數為2.1以上。 [數4](於式(2)中,n表示(B)環氧樹脂中所包含之環氧樹脂成分之種類數,Bk
表示(B)環氧樹脂中所包含之第k種環氧樹脂成分之環氧基數,Yk
表示(B)環氧樹脂中之第k種環氧樹脂成分之質量基準之含有比率) 關於上述式(2),例如,於(B)環氧樹脂為3種環氧樹脂成分之混合物之情形時,n為3。此時,3種環氧樹脂分別表示為成分1、成分2、成分3,各成分之環氧基數由B1
、B2
、B3
表示。又,(B)環氧樹脂中之成分B1
、B2
、B3
之質量基準之含有比率分別由Y1
、Y2
、Y3
表示。此時之平均氰酸酯基數利用[(B1
×Y1
)+(B2
×Y2
)+(B3
+Y3
)]/100進行計算。本發明中所使用之(B)環氧樹脂之上述平均環氧基數之值較佳為2.2~5.0,更佳為2.5~4.0。於平均環氧基數小於上述範圍之情形時,有硬化物之Tg不提高且耐熱性降低之傾向,於大於上述範圍之情形時,除難以獲得對應之環氧樹脂以外,有樹脂組合物之黏度亦增高,實用性較差之傾向。 於本發明中所使用之(B)環氧樹脂包含1種環氧樹脂之情形時,較佳為該環氧樹脂之環氧基數為上述範圍。又,於本發明之(B)環氧樹脂為複數種環氧樹脂之混合物之情形時,較佳為藉由調整混合物中之環氧樹脂之調配量,使混合物之上述平均環氧基數成為上述範圍。 關於本發明之(B)環氧樹脂,具體而言,例如可列舉:對苯二酚、間苯二酚、鄰苯二酚、間苯三酚等單核多酚化合物之聚縮水甘油醚化合物;二羥基萘、聯苯二酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、亞異丙基雙(鄰甲酚)、四溴雙酚A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺基雙酚、氧基雙酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆、萜酚等多核多酚化合物之聚縮水甘油醚化合物;α-萘酚、β-萘酚、1,5-二羥基萘、1,6-二羥基萘、2,6-二羥基萘等含萘骨架之二醇,及使該等二醇與醛於酸性觸媒下縮合而得之化合物之聚縮水甘油醚即萘型環氧樹脂;9,9-雙[4-(2-羥基乙氧基)苯基]茀、9,9-雙(4-羥基苯基)茀、9,9-雙(4-羥基-3-甲基苯基)茀等具有茀骨架之二醇之二縮水甘油醚即茀型環氧樹脂;乙二醇、丙二醇、丁二醇、己二醇、聚二醇、硫代雙乙醇、二環戊二烯二甲醇、2,2-雙(4-羥基環己基)丙烷(氫化雙酚A)、甘油、三羥甲基丙烷、季戊四醇、山梨糖醇、雙酚A-環氧乙烷加成物等多元醇類之聚縮水甘油醚;順丁烯二酸、反丁烯二酸、伊康酸、丁二酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、均苯三甲酸、均苯四甲酸、四氫鄰苯二甲酸、六氫鄰苯二甲酸、內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸之縮水甘油酯類及甲基丙烯酸縮水甘油酯之均聚物或共聚物;N,N-二縮水甘油苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)-2-甲基苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)苯胺、N,N,N',N'-四(2,3-環氧丙基)-4,4'-二胺基二苯基甲烷等具有縮水甘油基胺基之環氧化合物;乙烯基環己烯二環氧化物、二環戊二烯二環氧化物、3,4-環氧環己烷羧酸3,4-環氧環己基甲酯、6-甲基環己烷羧酸3,4-環氧-6-甲基環己基甲酯、己二酸雙(3,4-環氧-6-甲基環己基甲基)酯等環狀烯烴化合物之環氧化物;環氧化聚丁二烯、環氧化苯乙烯-丁二烯共聚物等環氧化共軛二烯聚合物;異氰尿酸三縮水甘油酯等雜環化合物。又,該等環氧樹脂亦可為藉由末端異氰酸酯之預聚物進行內部交聯而得者、或者利用多價之活性氫化合物(多酚、聚胺、含羰基之化合物、聚磷酸酯等)進行高分子量化而得者。 於上述所列舉之環氧樹脂之中,自對於纖維之含浸性良好之觀點而言,較佳為液狀者,自獲得之容易性及平均環氧基數之調整較為容易之觀點而言,更佳為單核多酚化合物之聚縮水甘油醚化合物、多核多酚化合物之聚縮水甘油醚化合物、茀型環氧樹脂、多元醇類之聚縮水甘油醚、具有縮水甘油基胺基之環氧化合物,尤佳為雙酚A型環氧樹脂、雙酚F型環氧樹脂、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)-2-甲基苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)苯胺、及N,N,N',N'-四(2,3-環氧丙基)-4,4'-二胺基二苯基甲烷。 於使用氰酸酯及環氧樹脂之硬化體系中,於過度提高交聯密度之情形時,有硬化物變得過於強韌而應用於纖維強化塑膠時之應力緩和性下降,無法獲得令人滿意之纖維強化塑膠之傾向。反之,於交聯密度過低之情形時,存在難以進行高分子量化,於硬化物之強度方面存在問題之情況。因此,有必要調整(A)氰酸酯與(B)環氧樹脂進行反應之官能基(氰酸酯基、環氧基)之基數。即,於本發明中,必須將上述式(1)所表示之平均氰酸酯基數設為2.1以上,及/或將上述式(2)所表示之平均環氧基數設為2.1以上。於本發明中,於對平均氰酸酯基數及平均環氧基數進行研究之情形時,相較於增加上述式(1)所表示之平均氰酸酯基數,增加上述式(2)所表示之平均環氧基數自可進一步提高硬化物之Tg之方面而言較佳。該情形時之平均環氧基數較佳為2.2~5.0,更佳為2.5~4.0。 於將平均環氧基數設為2.1以上之情形時,平均氰酸酯基數亦可未達2.1,較佳為1.8以上,更佳為1.9以上,進而較佳為2.0以上。 [(C)於25℃下為液狀之芳香族胺系硬化劑] 本發明中所使用之(C)於25℃下為液狀之芳香族胺系硬化劑係為了可容易地滲透至纖維材料,於25℃下為液狀,進而芳香環上直接具備胺基之化合物。作為此種化合物,例如可列舉:二胺基二甲基二苯基甲烷、二胺基二乙基二苯基甲烷、二胺基二乙基甲苯、1-甲基-3,5-雙(甲硫基)-2,4-苯二胺、1-甲基-3,5-雙(甲硫基)-2,6-苯二胺等。 該等之中,自硬化物之耐熱性提高之觀點而言,較佳為二胺基二苯基甲烷、二胺基二甲基二苯基甲烷、及二胺基二乙基甲苯,更佳為二胺基二乙基二苯基甲烷。 於本發明中,關於(C)於25℃下為液狀之芳香族胺系硬化劑之使用量,相對於(B)環氧樹脂100質量份,較佳為20~100質量份,更佳為40~90質量份。於少於20質量份之情形,或者多於100質量份之情形時,有樹脂組合物不完全硬化之傾向。 本發明之纖維強化塑膠用樹脂組合物存在含有(D)光吸收性成分之情況。於含有(D)光吸收性成分之情形時,可藉由照射活性能量線而進一步縮短硬化時間。藉由硬化時間變短,作業時間變短,又,與加熱硬化之情形相比,不僅由於以較少能量進行硬化而較為經濟,而且於環境方面亦有利。 本發明之樹脂組合物中所含有之(D)光吸收性成分係可吸收上述活性能量線,並釋放熱能之成分,可利用所釋放之熱能使樹脂組合物硬化。作為此種光吸收性成分,自於纖維與纖維之間滲透樹脂組合物之觀點而言,較佳為於25℃下為液狀者,或者與其他材料混合時相溶而成為液狀者。作為此種化合物,可列舉:苯胺黑、金屬錯合物、方酸衍生物、亞銨染料、聚次甲基、酞菁系化合物、萘酚菁系化合物、苝系化合物、四萘嵌三苯(quarterylene)系化合物、苯胺黑系化合物等。於本發明中,該等化合物之中,自可容易地獲得之方面而言,較佳為使用苯胺黑系化合物。 作為市售之苯胺黑系化合物,可列舉:Orient Chemical Industries(股)製造之BONASORB系列、eBIND ACW系列、eBIND LTW系列、eBIND LAW系列、ORIENT NIGROSINE系列、NUBIAN BLACK系列等。於本發明中,該等苯胺黑系化合物之中,自廉價且容易獲得之方面而言,較佳為使用NUBIAN BLACK系列。該等苯胺黑系化合物可單獨使用1種,亦可併用2種以上。 本發明之樹脂組合物中所含有之(D)光吸收性成分之調配量相對於樹脂組合物之總量為0.001~1質量%之範圍即可。若考慮樹脂組合物之硬化速度與放熱(組合物之焦化)之平衡性之觀點,則較佳為0.01~0.5質量%,進而較佳為0.05~0.2質量%。若少於0.001%,則僅藉由活性能量線照射會放熱不足,樹脂組合物難以完全硬化。又,於多於1%之情形時,於樹脂組合物之表面,活性能量線幾乎全被吸收,由於僅樹脂組合物之表面碳化而活性能量未通至內部,故而難以完全硬化至樹脂組合物之內部。 [添加劑] 本發明之樹脂組合物中,根據需要,亦可併用添加劑。 作為上述添加劑,例如可列舉:鄰苯二甲酸二辛酯、鄰苯二甲酸二丁酯、苯甲醇、煤焦油等非反應性之稀釋劑(塑化劑);顏料;γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-N'-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-苯胺基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三乙氧基矽烷、乙烯基三乙氧基矽烷、N-β-(N-乙烯基苄基胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-氯丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷、γ-異氰酸酯基丙基三乙氧基矽烷等矽烷偶合劑;三異硬脂醯基鈦酸異丙酯、三(正十二烷基苯磺醯基)鈦酸異丙酯、三(二辛基焦磷醯氧基)鈦酸異丙酯、雙(二辛基亞磷醯氧基)鈦酸四異丙酯、雙(二-十三烷基亞磷醯氧基)鈦酸四辛酯、雙(二-十三烷基)亞磷醯氧基鈦酸四(2,2-二烯丙氧基甲基-1-丁基)酯、雙(二辛基焦磷醯氧基)羥乙酸鈦酸酯、雙(二辛基焦磷醯氧基)鈦酸乙二酯、三辛醯基鈦酸異丙酯、二甲基丙烯醯基異硬脂醯基鈦酸異丙酯、異硬脂醯基二丙烯醯基鈦酸異丙酯、三(二辛基磷醯氧基)鈦酸異丙酯、三(異丙苯基苯基)鈦酸異丙酯、三(N-胺基乙基-胺基乙基)鈦酸異丙酯、鈦酸四異丙酯、鈦酸四正丁酯、鈦酸丁酯二聚物、鈦酸四(2-乙基己基)酯、鈦酸四硬脂酯、鈦酸四甲酯、二乙氧基雙(乙醯丙酮)鈦、二異丙基雙(乙醯丙酮)鈦、二異丙氧基雙(乙醯乙酸乙酯)鈦、異丙氧基(2-乙基-1,3-己二醇)鈦、二(2-乙基己氧基)雙(2-乙基-1,3-己二醇)鈦、二正丁氧基(三乙醇胺)鈦、四乙醯丙酮酸鈦、羥基雙(乳酸)鈦、二異丙苯基苯基羥乙酸鈦酸酯、二異硬脂醯基鈦酸乙二酯等鈦偶合劑;新烷氧基三新癸醯基鋯酸酯、新烷氧基三(十二烷基)苯磺醯基鋯酸酯、新烷氧基三(二辛基)磷醯氧基鋯酸酯、新烷氧基三(二辛基)焦磷醯氧基鋯酸酯、新烷氧基三(伸乙基二胺基)乙基鋯酸酯、新烷氧基三(間胺基)苯基鋯酸酯、四(2,2-二烯丙氧基甲基)丁基,二(二-十三烷基)亞磷醯氧基鋯酸酯、新戊基(二烯丙基)氧基,三新癸醯基鋯酸酯、新戊基(二烯丙基)氧基,三(十二烷基)苯-磺醯基鋯酸酯、新戊基(二烯丙基)氧基,三(二辛基)磷酸醯氧基鋯酸酯、新戊基(二烯丙基)氧基,三(二辛基)焦磷醯氧基鋯酸酯、新戊基(二烯丙基)氧基,三(N-伸乙基二胺基)乙基鋯酸酯、新戊基(二烯丙基)氧基,三(間胺基)苯基鋯酸酯、新戊基(二烯丙基)氧基,三甲基丙烯醯基鋯酸酯、新戊基(二烯丙基)氧基,三丙烯醯基鋯酸酯、二新戊基(二烯丙基)氧基,二對胺基苯甲醯基鋯酸酯、二新戊基(二烯丙基)氧基,二(3-巰基)丙醯氧基鋯酸酯、鋯(IV)2,2-雙(2-丙氧基甲基)丁氧基,環二[2,2-(雙2-丙氧基甲基)丁氧基]焦磷醯氧基-O,O、新烷氧基三新癸醯基鋯酸酯、新烷氧基三(十二烷基)苯磺醯基鋯酸酯、新烷氧基三(二辛基)磷醯氧基鋯酸酯、新烷氧基三(二辛基)焦磷醯氧基鋯酸酯、新烷氧基三(伸乙基二胺基)乙基鋯酸酯、新烷氧基三(間胺基)苯基鋯酸酯,以及作為鋯系偶合劑之四正丙氧基鋯、四正丁氧基鋯、四乙醯丙酮鋯、三丁氧基乙醯丙酮鋯、三丁氧基硬脂酸鋯、二丁氧基雙(乙醯丙酮)鋯、二丁氧基雙(乙醯丙酮)鋯、三丁氧基乙醯乙酸乙酯鋯、單丁氧基乙醯丙酮鋯雙(乙醯乙酸乙酯)等鋯系偶合劑;堪地里拉蠟、巴西棕櫚蠟、木蠟、蟲蠟、蜂蠟、羊毛脂、鯨蠟、褐煤蠟、石油蠟、脂肪酸蠟、脂肪酸酯、脂肪酸醚、芳香族酯、芳香族醚等潤滑劑;增黏劑;觸變劑;抗氧化劑;光穩定劑;紫外線吸收劑;阻燃劑;消泡劑;防銹劑等常用之添加劑。 上述所列舉之添加劑之中,自向纖維含浸之觀點而言,較佳為於25℃下為液狀者,或者溶解於氰酸酯、環氧樹脂、芳香族胺系硬化劑中者,自對纖維之密接性提高之方面而言,更佳為添加矽烷偶合劑,自容易獲得且廉價之方面而言,進而較佳為添加γ-胺基丙基三乙氧基矽烷、及/或γ-縮水甘油氧基丙基三乙氧基矽烷,尤佳為添加γ-縮水甘油氧基丙基三乙氧基矽烷。 關於上述所列舉之矽烷偶合劑之調配量,相對於(B)環氧樹脂100重量份,較佳為調配0.1~50質量份,自與樹脂之溶混性良好,且與纖維之密接性提高之方面而言,更佳為調配7~20質量份。 本發明之硬化物係使本發明之纖維強化塑膠用樹脂組合物硬化而成。使本發明之纖維強化塑膠用樹脂組合物硬化之方法無特別限制,可利用公知之方法進行硬化。具體而言,本發明之纖維強化塑膠用樹脂組合物亦可利用加熱進行硬化。又,於本發明之纖維強化塑膠用樹脂組合物含有(D)光吸收性成分之情形時,可藉由照射活性能量線而縮短硬化時間。藉由硬化時間變短,作業時間變短,又,與加熱硬化之情形相比,不僅由於以較少能量進行硬化而較為經濟,而且於環境方面亦有利。 上述活性能量線並無特別限制,可根據目的進行適當選擇。作為該活性能量線,例如可列舉:電子束、紫外線、紅外線、雷射光線、可見光線、電離放射線(X射線、α射線、β射線、γ射線等)、微波、高頻等。 本發明中,該等活性能量線之中,自進一步提高硬化速度之觀點而言,較佳為使用雷射光線及/或紅外線,更佳為使用紅外線。 作為上述雷射光線,可列舉:以紅寶石、玻璃、YAG(於釔、鋁、石榴石中添加有微量稀土元素之結晶體)作為介質之固體雷射;以將色素溶解於水或醇等溶劑中而得者作為介質之液體雷射;以CO2
、氬、或He-Ne混合氣體等作為介質之氣體雷射;利用半導體之再結合發光之半導體雷射。於本發明中,較佳為使用廉價且輸出之控制較為容易之半導體雷射。 本發明中所使用之雷射光線之波長並無特別限制,例如,若為近紅外線區域(波長大約為0.7~2.5 μm),則可使樹脂組合物硬化。雷射光線之輸出亦無特別限制,例如,可於1 W~4 kW之範圍內使樹脂組合物硬化。 照射雷射之時間亦無特別限制,根據照射面積或輸出為各種範圍,例如,可於0.2 W/mm2
~10 W/mm2
之範圍內使樹脂組合物硬化。使本發明之樹脂組合物硬化之紅外線之波長亦無特別限制。例如,近紅外線區域(波長大約為0.7~2.5 μm)、中紅外線區域(波長大約為2.5~4 μm)、及遠紅外線區域(波長大約為4~1000 μm)等任一區域之波長均可使樹脂組合物硬化。 作為照射使本發明之樹脂組合物硬化之紅外線之方法,可列舉使用紅外線加熱器進行照射之方法。作為紅外線加熱器,例如可列舉:鹵素加熱器、石英加熱器、封裝加熱器、及陶瓷加熱器等。鹵素加熱器可照射具有近紅外線區域至中紅外線區域之波長之紅外線,石英加熱器、封裝加熱器、及陶瓷加熱器可照射具有中紅外區域至遠紅外區域之波長之紅外線。該等之中,自接通電源之後直至熱源被加熱之時間較短,可迅速加熱之理由而言,較佳為使用鹵素加熱器。 使本發明之樹脂組合物硬化之紅外線之波長並無特別限制,根據所使用之光吸收性成分之吸收區域,可使用各種波長區域。例如,於使用苯胺黑系化合物之情形時,於近紅外線區域(波長大約為0.7~2.5 μm)中,可以短時間使本發明之樹脂硬化物硬化。 本發明之纖維強化塑膠可藉由使均勻含有本發明之纖維強化塑膠用樹脂組合物及強化纖維之纖維強化塑膠之基質樹脂(組合物)硬化而獲得。於本發明中,所謂均勻含有纖維強化塑膠用樹脂組合物及強化纖維,表示樹脂組合物不停留於表面,而完全遍及至纖維內部。強化纖維之種類並無特別限制,例如可單獨使用碳纖維、玻璃纖維、芳香族聚醯胺纖維、硼纖維、氧化鋁纖維、聚矽氧碳化物纖維等,亦可製成2種以上之混合纖維而使用。 作為上述所列舉之強化纖維之形態,可列舉將高強度、高彈性模數纖維沿單方向排列之所謂絲束片、或將上述纖維絲狀沿單方向或雙方向排列之單方向性梭織物或雙方向性梭織物、沿三方向排列之三軸梭織物、沿多方向排列之多軸梭織物等。於絲束片中,為了提高向基材之樹脂含浸性,可以於線料間確保適度之間隙之方式排列上述纖維。 本發明之強化纖維相對於纖維強化塑膠用樹脂組合物之使用量並無特別限制,可根據所得之纖維強化塑膠之用途適當地決定,例如,相對於纖維強化塑膠用樹脂組合物整體之體積,強化纖維之體積含有率較佳為45~70%,更佳為50~65%。又,使纖維強化塑膠之基質樹脂硬化之方法亦無特別限制,例如,可與上述之本發明之纖維強化塑膠用樹脂組合物之硬化方法同樣地進行硬化。 關於用於成形使用本發明之樹脂組合物之纖維強化塑膠之方法,並無特別限制,例如可列舉:擠壓成形法、吹塑成形法、壓縮成形法、真空成形法、射出成形法、RTM(Resin Transfer Molding,樹脂轉注成形)成形、VaRTM(Vaccum assist Resin Transfer Molding,真空輔助樹脂轉注成形)成形、積層成形、手工塗佈成形、長絲纏繞成形法等。 使用本發明之樹脂組合物而得之纖維強化塑膠可利用於各種用途。例如可列舉:汽車、船舶及軌道車輛等移動體之結構材料;驅動軸、板彈簧、風車葉片、壓力容器、慣性輪、製紙用輥、屋頂材料、纜線、及維護補強材料等普通工業用途;機身、主翼、尾翼、動翼、整流罩(fairing)、通風罩、門、座位、內飾材料、馬達殼體、天線等航空航天用途;高爾夫桿身、釣魚竿、網球或羽毛球之球拍用途、曲棍球等之球棒用途、及滑雪杖用途等運動用途。 [實施例] 以下,藉由實施例具體地說明本發明。再者,於以下之實施例等中,%只要無特別說明,則表示質量基準。 [實施例1] 向500 mL一次性杯子中,加入作為(A)氰酸酯之LECy(1,1-雙(4-氰酸基苯基)乙烷;龍沙公司製造,平均氰酸酯基數:2)100 g、作為(B)環氧樹脂之Adeka Resin EP-4901E(雙酚F型環氧樹脂,ADEKA(股)製造,環氧當量:170 g/eq.,平均環氧基數:2)75 g、MY-0510(N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)-2-甲基苯胺,Huntsman公司製造,環氧當量:101 g/eq.,平均環氧基數:3)12.5 g、作為(C)於25℃下為液狀之芳香族胺系硬化物之Kayahard AA(二胺基二乙基二苯基甲烷,日本化藥(股)製造)70 g,於25℃下以刮勺攪拌5分鐘。此後,使用行星式攪拌機進一步攪拌,獲得調配物。針對所得之調配物,藉由以下之方法進行玻璃轉移點溫度(Tg)、彎曲試驗之評價。 <Tg測定> 藉由下述方式測定Tg,即,測量上述調配物5 mg置於示差掃描熱量測定用之托盤,以80℃加熱5小時,此後進一步以150℃加熱2小時而進行硬化後,利用示差掃描熱量計(DSC6220ASD-2,Seiko Instruments(股)製造),以10℃/分鐘之升溫條件進行加熱,讀取示差掃描熱量之反曲點。將結果示於表1。 <彎曲試驗> 針對玻璃纖維(UDR S14EU970-01190-00100-100000,SAERTEX公司製造)100 g,使用輥含浸所得之調配物33 g。此後,將含浸有樹脂之玻璃纖維放入150℃之恆溫槽中,歷時3小時使樹脂硬化。針對所得之樹脂硬化後之樹脂纖維複合物(纖維強化塑膠),利用依據JIS K 7057之方法測定上降伏點應力、最大點應力、彈性模數、層間剪切。將結果示於表1。 [實施例2~實施例8、比較例1] 除如表1所示般改變調配以外,進行與實施例1相同之操作,獲得實施例2~3及比較例1之調配物。針對所得之調配物,與實施例1同樣地進行Tg及彎曲試驗之評價。將結果示於表1。 [表1]
如表1之結果所示,本發明之樹脂組合物之Tg之值良好,於含浸於纖維且硬化後之纖維強化塑膠中,彎曲試驗亦取得優異之結果。關於未使用本發明之樹脂組合物之纖維強化塑膠作為纖維強化塑膠時之物性,雖然某種程度上有良好評價,但Tg則無法獲得令人滿意之結果。 [產業上之可利用性] 關於使用本發明之纖維強化塑膠用樹脂組合物及強化纖維而製造之纖維強化塑膠,由於除耐熱性良好以外,拉伸或彎曲物性亦優異,故而可應用於船舶、汽車、飛機等運輸機;運動用品、洗面台、窗框等建築材料;高壓氣體鋼瓶、風力發電用葉片等工業機件等廣泛之領域。
Claims (6)
- 一種纖維強化塑膠用樹脂組合物,其含有(A)氰酸酯、(B)環氧樹脂、及(C)於25℃下為液狀之芳香族胺系硬化劑,(B)環氧樹脂含有選自由N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)-2-甲基苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)苯胺、及N,N,N',N'-四(2,3-環氧丙基)-4,4'-二胺基二苯基甲烷所組成之群中之至少1種多官能環氧樹脂,且下述式(1)所表示之(A)氰酸酯之平均氰酸酯基數為2.1以上且4.1以下,及/或下述式(2)所表示之(B)環氧樹脂之平均環氧基數為2.1以上,
- 如請求項1至3中任一項之纖維強化塑膠用樹脂組合物,其中(C)於25℃下為液狀之芳香族胺系硬化劑係於25℃下為液狀,進而芳香環上直接具備胺基之化合物。
- 一種硬化物,其係使如請求項1至3中任一項之纖維強化塑膠用樹脂組合物硬化而成者。
- 一種纖維強化塑膠,其係使含有如請求項1至3中任一項之樹脂組合物及強化纖維之組合物硬化而成者。
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EP (1) | EP3587492A4 (zh) |
JP (1) | JP7121721B2 (zh) |
KR (1) | KR102573168B1 (zh) |
CN (1) | CN110177838B (zh) |
CA (1) | CA3050075A1 (zh) |
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JPWO2019111416A1 (ja) * | 2017-12-08 | 2020-12-10 | 昭和電工マテリアルズ株式会社 | プリプレグ、積層板、及びそれらの製造方法、並びにプリント配線板及び半導体パッケージ |
US11319435B2 (en) * | 2018-02-27 | 2022-05-03 | Toray Industries, Inc. | Heat-curable resin composition, prepreg, and fiber-reinforced composite material |
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WO2015082613A1 (en) * | 2013-12-04 | 2015-06-11 | Lonza Ltd | Method for preparing fiber-reinforced parts based on cyanate ester/epoxy blends |
WO2016095903A1 (de) * | 2014-12-19 | 2016-06-23 | Airbus Defence and Space GmbH | Hochtemperaturbeständige duromere auf der grundlage von naphthalin-basierten epoxidharzen und cyanatestern sowie verbesserung der schlagzähigkeit |
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US4142034A (en) * | 1978-04-10 | 1979-02-27 | Cincinnati Milacron Inc. | Epoxy resin compositions containing an amine-cyanic acid ester combination curing agent |
JPS62246924A (ja) | 1986-04-18 | 1987-10-28 | Toray Ind Inc | 硬化性樹脂組成物 |
JP3508346B2 (ja) * | 1994-12-02 | 2004-03-22 | 東レ株式会社 | プリプレグおよび繊維強化複合材料 |
JP5105657B2 (ja) | 2000-04-14 | 2012-12-26 | 三菱瓦斯化学株式会社 | プリプレグ及び積層板 |
JP4938567B2 (ja) * | 2007-06-29 | 2012-05-23 | 株式会社Adeka | 一液型シアネート−エポキシ複合樹脂組成物 |
JP5517326B2 (ja) | 2008-06-27 | 2014-06-11 | 株式会社Adeka | 一液型シアネート−エポキシ複合樹脂組成物 |
JP2010174242A (ja) | 2009-12-28 | 2010-08-12 | Sumitomo Bakelite Co Ltd | ビフェニルアラルキル型シアン酸エステル樹脂、並びにビフェニルアラルキル型シアン酸エステル樹脂を含む樹脂組成物、及び、当該樹脂組成物を用いてなるプリプレグ、積層板、樹脂シート、多層プリント配線板、並びに半導体装置 |
JP5603610B2 (ja) | 2010-02-12 | 2014-10-08 | 株式会社Adeka | 無溶剤一液型シアン酸エステル−エポキシ複合樹脂組成物 |
JP2014019815A (ja) | 2012-07-20 | 2014-02-03 | Mitsubishi Gas Chemical Co Inc | 硬化性樹脂組成物、およびその硬化物 |
JP6637253B2 (ja) | 2015-05-12 | 2020-01-29 | 株式会社Adeka | エポキシ樹脂組成物、及び、それを用いた繊維強化プラスチック |
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EP3345950B1 (en) * | 2015-09-04 | 2021-07-21 | Adeka Corporation | Resin composition for fiber-reinforced plastic, cured product thereof, fiber-reinforced plastic containing said cured product, and method for producing said fiber-reinforced plastic |
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WO2015082613A1 (en) * | 2013-12-04 | 2015-06-11 | Lonza Ltd | Method for preparing fiber-reinforced parts based on cyanate ester/epoxy blends |
WO2016095903A1 (de) * | 2014-12-19 | 2016-06-23 | Airbus Defence and Space GmbH | Hochtemperaturbeständige duromere auf der grundlage von naphthalin-basierten epoxidharzen und cyanatestern sowie verbesserung der schlagzähigkeit |
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JPWO2018155672A1 (ja) | 2019-12-19 |
CN110177838A (zh) | 2019-08-27 |
EP3587492A1 (en) | 2020-01-01 |
JP7121721B2 (ja) | 2022-08-18 |
CA3050075A1 (en) | 2018-08-30 |
US11649319B2 (en) | 2023-05-16 |
EP3587492A4 (en) | 2020-11-25 |
CN110177838B (zh) | 2023-08-11 |
WO2018155672A1 (ja) | 2018-08-30 |
KR102573168B1 (ko) | 2023-09-06 |
KR20190120173A (ko) | 2019-10-23 |
TW201842027A (zh) | 2018-12-01 |
US20210130538A1 (en) | 2021-05-06 |
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