WO2023223912A1 - 熱硬化性樹脂組成物、及び、硬化物 - Google Patents
熱硬化性樹脂組成物、及び、硬化物 Download PDFInfo
- Publication number
- WO2023223912A1 WO2023223912A1 PCT/JP2023/017570 JP2023017570W WO2023223912A1 WO 2023223912 A1 WO2023223912 A1 WO 2023223912A1 JP 2023017570 W JP2023017570 W JP 2023017570W WO 2023223912 A1 WO2023223912 A1 WO 2023223912A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- examples
- polyamide
- thermosetting
- resin composition
- Prior art date
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- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 91
- 239000011342 resin composition Substances 0.000 title claims abstract description 74
- 229920005989 resin Polymers 0.000 claims abstract description 185
- 239000011347 resin Substances 0.000 claims abstract description 185
- 239000002245 particle Substances 0.000 claims abstract description 138
- 229920006122 polyamide resin Polymers 0.000 claims abstract description 83
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 42
- 239000003822 epoxy resin Substances 0.000 claims description 37
- 229920000647 polyepoxide Polymers 0.000 claims description 37
- 125000002723 alicyclic group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- 125000000524 functional group Chemical group 0.000 claims description 15
- 230000005484 gravity Effects 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- -1 glycidyl ester Chemical class 0.000 description 39
- 239000000047 product Substances 0.000 description 39
- 239000003795 chemical substances by application Substances 0.000 description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
- 150000001335 aliphatic alkanes Chemical class 0.000 description 15
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000005011 phenolic resin Substances 0.000 description 12
- 239000000835 fiber Substances 0.000 description 11
- 239000011159 matrix material Substances 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000012736 aqueous medium Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 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 10
- 238000002844 melting Methods 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 239000012783 reinforcing fiber Substances 0.000 description 10
- 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 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000002460 imidazoles Chemical class 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 7
- 229920000299 Nylon 12 Polymers 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000004760 aramid Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 229920003235 aromatic polyamide Polymers 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 150000003951 lactams Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 5
- 241001120493 Arene Species 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 229920006152 PA1010 Polymers 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- 239000004953 Aliphatic polyamide Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 229920003231 aliphatic polyamide Polymers 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004843 novolac epoxy resin Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- 229920000572 Nylon 6/12 Polymers 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 2
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- OGRULRAOMCDCBO-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC1=CC=C2C=CC=CC2=C1OCC1CO1 OGRULRAOMCDCBO-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 229920000571 Nylon 11 Polymers 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 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
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000004984 aromatic diamines Chemical class 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
- 229910052796 boron Inorganic materials 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 2
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- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 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
- 229920003023 plastic Polymers 0.000 description 2
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000011134 resol-type phenolic resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229920006017 homo-polyamide Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229920003196 poly(1,3-dioxolane) Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- NNOBHPBYUHDMQF-UHFFFAOYSA-N propylphosphine Chemical compound CCCP NNOBHPBYUHDMQF-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920003170 water-soluble synthetic polymer Polymers 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Definitions
- the present disclosure relates to a thermosetting resin composition and a cured product.
- thermosetting resin composition having a thermosetting resin and resin particles containing a polyamide resin has been used from the viewpoint of increasing the toughness of a cured product obtained by curing the thermosetting resin composition (for example, Patent Document 1).
- the polyamide resin contained in the resin particles is a resin that relatively easily absorbs moisture.
- the resin particles in the thermosetting resin composition in order to suppress voids contained in the cured product and to facilitate mixing of the resin particles and the thermosetting resin, It may be required to suppress the moisture contained in the particles. That is, resin particles that are difficult to absorb moisture may be required.
- the first object of the present disclosure is to provide a thermosetting resin composition in which the cured product has high toughness and in which resin particles are difficult to absorb moisture.
- the second objective is to provide a cured product.
- a first aspect of the present disclosure is a thermosetting resin composition
- a thermosetting resin composition comprising a thermosetting resin and resin particles,
- the resin particles contain a polyamide resin and a polyolefin resin
- the present invention relates to a thermosetting resin composition in which the content of the polyamide resin in the resin particles is 50% by weight or more.
- the second aspect of the present disclosure relates to a cured product obtained by thermosetting the thermosetting resin composition.
- thermosetting resin composition in which the cured product has high toughness and resin particles hardly absorb moisture. Further, according to the present disclosure, it is possible to provide a cured product obtained by thermosetting the thermosetting resin composition.
- Example C-1 SEM photograph of a cross section of a resin particle in Example C-1 (in the cross section, the resin particle has been etched with toluene, and the holed portion is the portion where the polyolefin resin was).
- thermosetting resin composition according to this embodiment includes a thermosetting resin and resin particles.
- the resin particles contain a polyamide resin and a polyolefin resin.
- the content of the polyamide resin in the resin particles is 50% by weight or more.
- thermosetting resin examples include epoxy resin, phenol resin, unsaturated polyester resin, vinyl ester resin, acrylic resin, urea resin, melamine resin, aniline resin, polyimide resin, and bismaleimide resin. These thermosetting resins may be used alone or in combination of two or more.
- thermosetting resin epoxy resins and phenol resins are preferable, and epoxy resins are particularly preferable. Since epoxy resin and polyamide resin have excellent compatibility, when the thermosetting resin contains epoxy resin, the resin particles containing the polyamide resin are easily dispersed in the epoxy resin, and the toughness due to the resin particles is increased. The effect of improvement will be more easily realized.
- epoxy resins examples include glycidyl ether type epoxy resins, glycidyl amine type epoxy resins, glycidyl ester type epoxy resins, alkene oxides (such as vinyl cyclohexene dioxide), triglycidyl isocyanurate, and the like.
- Examples of the glycidyl ether type epoxy resin include bisphenol type epoxy resin, phenol type epoxy resin, dicyclopentadiene type epoxy resin, epoxy resin having an aromatic skeleton (polyglycidyl ether), alkanediol diglycidyl ether, and polyalkanediol.
- Examples include diglycidyl ether, epoxy resin having an aliphatic skeleton (polyglycidyl ether), and the like.
- Examples of the bisphenol type epoxy resin include a reaction product of bisphenols and epichlorohydrin, a reaction product of an alkylene oxide adduct of bisphenols and epichlorohydrin, and the like.
- Examples of the bisphenols include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, and brominated bisphenol epoxy resin.
- the number of moles of alkylene oxide added per mole of hydroxyl group of the bisphenol is, for example, 1 mole or more (for example, 1 to 20 moles), preferably 1 to 15 moles, more preferably 1 mole. ⁇ 10 moles.
- phenolic epoxy resin examples include phenol novolak epoxy resin, cresol novolac epoxy resin, naphthol novolac epoxy resin, bisphenol A novolac epoxy resin, bisphenol F novolac epoxy resin, biphenyl skeleton-containing phenol novolak resin, and xylylene.
- phenol novolak epoxy resin cresol novolac epoxy resin, naphthol novolac epoxy resin, bisphenol A novolac epoxy resin, bisphenol F novolac epoxy resin, biphenyl skeleton-containing phenol novolak resin, and xylylene.
- cresol novolac epoxy resin cresol novolac epoxy resin
- naphthol novolac epoxy resin bisphenol A novolac epoxy resin
- bisphenol F novolac epoxy resin bisphenol F novolac epoxy resin
- biphenyl skeleton-containing phenol novolak resin examples include skeleton-containing phenol novolac resins.
- Examples of the epoxy resin (polyglycidyl ether) having an aromatic skeleton include glycidyl ether having a naphthalene skeleton.
- Examples of the glycidyl ether having a naphthalene skeleton include di(glycidyloxy)naphthalene, bis[2,7-di(glycidyloxy)naphthyl]methane, and the like.
- Examples of the di(glycidyloxy)naphthalene include 1,5-di(glycidyloxy)naphthalene.
- alkanediol diglycidyl ether examples include C 2-10 alkanediol diglycidyl ether.
- Examples of the C 2-10 alkanediol diglycidyl ether include butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, and the like.
- Examples of the polyalkanediol diglycidyl ether include polyC 2-4 alkanediol diglycidyl ether.
- Examples of the polyC 2-4 alkanediol diglycidyl ether include polypropylene glycol diglycidyl ether.
- Examples of the epoxy resin (polyglycidyl ether) having an aliphatic skeleton include glycidyl polyether of polyol.
- Examples of the polyols include alkanetriols, alkanetetraols, alkane pentaols, alkane hexaols, and the like.
- Examples of the alkane triol include C 3-10 alkane triol.
- Examples of the alkanetetraol include C 3-10 alkanetetraol.
- Examples of the glycidyl polyether include diglycidyl ether, triglycidyl ether, tetraglycidyl ether, pentaglycidyl ether, hexaglycidyl ether, and the like.
- Examples of the glycidyl polyether of the polyol include trimethylolpropane diglycidyl ether, trimethylolpropane triglycidyl ether, glycerin diglycidyl ether, and glycerin triglycidyl ether.
- Examples of the glycidylamine type epoxy resin include tetraglycidyldiaminodiphenylmethane, triglycidyl-p-aminophenol, triglycidyl aminocresol, diglycidylaniline, N,N-diglycidyl-4-glycidyloxyaniline, and the like.
- Examples of the glycidyl ester type epoxy resin include diglycidyl ester of dicarboxylic acid.
- Examples of the dicarboxylic acid include aromatic dicarboxylic acids, hydrogenated aromatic dicarboxylic acids, and the like.
- Examples of the aromatic dicarboxylic acids include terephthalic acid, isophthalic acid, phthalic acid, tetrahydrophthalic acid, and hexahydrophthalic acid.
- epoxy resins may be used alone or in combination of two or more.
- epoxy resins having an aromatic skeleton are preferred, and bisphenol type epoxy resins are particularly preferred.
- phenolic resin examples include resins having one or more, preferably two or more, phenolic hydroxyl groups in one molecule.
- examples of the phenol resin include novolac type phenol resin, resol type phenol resin, and polyoxystyrene resin.
- the novolac type phenol resin is a condensate of phenols and aldehydes.
- the novolac type phenolic resin is obtained, for example, by condensation polymerization of phenols and aldehydes in the presence of an acidic catalyst.
- the resol type phenolic resin is a condensate of phenols and aldehydes.
- the resol type phenolic resin is obtained, for example, by condensation polymerization of phenols and aldehydes in the presence of an alkaline catalyst.
- phenols examples include phenol, cresol, trimethylphenol, xylenol, resorcinol, catechol, butylphenol, octylphenol, nonylphenol, phenylphenol, dihydroxybenzene, bisphenol A, and naphthol.
- cresol examples include o-cresol, m-cresol, and p-cresol.
- trimethylphenol examples include 2,3,5-trimethylphenol.
- xylenol examples include 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 3,4-xylenol, and 3,5-xylenol.
- aldehydes examples include formaldehyde, paraformaldehyde, acetaldehyde, benzaldehyde, hydroxybenzaldehyde, glyoxal, glutaraldehyde, terephthalaldehyde, isophthalaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, 3-methylbutyraldehyde, and p-tolylaldehyde. , phenylacetaldehyde, and the like.
- hydroxybenzaldehyde examples include o-hydroxybenzaldehyde, m-hydroxybenzaldehyde, and p-hydroxybenzaldehyde.
- novolak-type phenolic resin examples include novolak resin (a condensate of phenol and formaldehyde), cresol novolak resin (a condensate of cresol and formaldehyde), and the like.
- the phenolic resins may be used alone or in combination of two or more.
- the hydroxyl equivalent of the phenol resin is preferably 50 to 500 g/eq. More preferably 100 to 350 g/eq. It is.
- thermosetting resin composition according to the present embodiment preferably contains a thermosetting resin in an amount of 40 to 99% by weight, more preferably 80 to 97% by weight.
- the resin particles are formed from a resin composition for resin particles containing a polyamide resin and a polyolefin resin.
- polyamide resin examples include aliphatic polyamide resin, alicyclic polyamide resin, and aromatic polyamide resin.
- the polyamide resin may be a homopolyamide resin or a copolyamide resin.
- the polyamide resin may have a first functional group.
- the first functional group include an amino group, a carboxy group, an acid anhydride group, an epoxy group, an isocyanate group, and a carbodiimide group.
- the amino group include "-NH 2 " and "-NHR".
- R is an alkyl group. Examples of R include a methyl group, an ethyl group, and a propyl group.
- the acid anhydride group include a carboxylic acid anhydride group.
- the aliphatic polyamide resin includes a polyamide resin of an aliphatic diamine component and an aliphatic dicarboxylic acid component, a polyamide resin of lactam, a polyamide resin of aminocarboxylic acid, a polyamide resin of an aliphatic diamine component and an aliphatic dicarboxylic acid component, and a lactam and/or Examples include polyamide resins with aminocarboxylic acids.
- aliphatic diamine component examples include C4-16 alkylene diamine (eg, tetramethylene diamine, hexamethylene diamine, dodecane diamine, etc.).
- the aliphatic diamine component is preferably a C6-14 alkylene diamine, more preferably a C6-12 alkylene diamine.
- aliphatic dicarboxylic acid component examples include C4-20 alkanedicarboxylic acids (eg, adipic acid, sebacic acid, dodecanedioic acid, etc.).
- the aliphatic dicarboxylic acid component is preferably a C5-16 alkanedicarboxylic acid, more preferably a C6-14 alkanedicarboxylic acid.
- lactams having 4 to 20 carbon atoms examples include lactams having 4 to 20 carbon atoms (eg, ⁇ -caprolactam, ⁇ -laurolactam, etc.).
- the lactam is preferably a lactam having 4 to 16 carbon atoms.
- aminocarboxylic acids examples include C4-20 aminocarboxylic acids (eg, ⁇ -aminoundecanoic acid, etc.).
- the aminocarboxylic acid is preferably a C4-16 aminocarboxylic acid, more preferably a C6-14 aminocarboxylic acid.
- Examples of the aliphatic polyamide resin include polyamide 6, polyamide 11, polyamide 12, polyamide 46, polyamide 66, polyamide 610, polyamide 611, polyamide 612, polyamide 613, polyamide 1010, polyamide 66/11, polyamide 66/12, Examples include polyamide 6/12/612.
- the alicyclic polyamide resin examples include polyamide resins having at least one component selected from an alicyclic diamine component and an alicyclic dicarboxylic acid component.
- the alicyclic polyamide resin includes, as a diamine component and a dicarboxylic acid component, an aliphatic diamine component and/or an aliphatic dicarboxylic acid component as exemplified above, along with an alicyclic diamine component and/or an alicyclic dicarboxylic acid component.
- Alicyclic polyamide resins are preferred.
- Such alicyclic polyamide resin has high transparency and is known as a so-called transparent polyamide resin.
- Examples of the alicyclic diamine component include diaminocycloalkanes, bis(aminocycloalkyl)alkanes, hydrogenated xylylene diamines, and the like.
- Examples of the diaminocycloalkane include diaminocyclohexane.
- the diaminocycloalkane is preferably diamino C5-10 cycloalkane.
- Examples of the bis(aminocycloalkyl)alkanes include bis(4-aminocyclohexyl)methane, bis(4-amino-3-methylcyclohexyl)methane, and 2,2-bis(4'-aminocyclohexyl)propane. Can be mentioned.
- the bis(aminocycloalkyl)alkane is preferably bis(aminoC5-8cycloalkyl)C1-3 alkane.
- the alicyclic diamine component may have a substituent such as an alkyl group.
- the alkyl group is preferably a C1-6 alkyl group, more preferably a C1-4 alkyl group, and still more preferably a C1-2 alkyl group (methyl group, ethyl group, etc.).
- alicyclic dicarboxylic acids examples include cycloalkanedicarboxylic acids (eg, cyclohexane-1,4-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid, etc.).
- Typical alicyclic polyamide resins include, for example, an alicyclic diamine component [e.g., bis(aminocyclohexyl)alkane, etc.] and an aliphatic dicarboxylic acid component [e.g., alkanedicarboxylic acid (e.g., C 4-20 alkanedicarboxylic acid)] acid components, etc.)].
- an alicyclic diamine component e.g., bis(aminocyclohexyl)alkane, etc.
- an aliphatic dicarboxylic acid component e.g., alkanedicarboxylic acid (e.g., C 4-20 alkanedicarboxylic acid)] acid components, etc.
- the aromatic polyamide resin is a concept that includes a polyamide resin containing at least one of an aromatic diamine component and an aromatic dicarboxylic acid component as a structural unit.
- the aromatic polyamide resin include polyamide resins in which both the diamine component of the structural unit and the dicarboxylic acid component of the structural unit are aromatic components (also called “fully aromatic polyamide resin", "aramid”, etc.). It will be done.
- the aromatic polyamide resin may be a modified polyamide resin. Examples of the modified polyamide resin include polyamide resins having a branched chain structure.
- Examples of the aromatic diamine component include metaxylylene diamine.
- the aromatic dicarboxylic acid component include terephthalic acid and isophthalic acid. Further, the aromatic dicarboxylic acid component may be a dimer acid or the like.
- the polyamide resins may be used alone or in combination of two or more.
- semi-crystalline polyamide resins for example, alicyclic polyamide resins, aliphatic polyamide resins, etc. are preferable because they have a large reinforcing effect.
- the number average molecular weight of the polyamide resin is, for example, 8,000 to 200,000, preferably 9,000 to 150,000, and more preferably 10,000 to 100,000.
- the number average molecular weight is measured from the polymethyl methacrylate (PMMA) equivalent molecular weight distribution using gel permeation chromatography (GPC) using hexafluoroisopropanol (HFIP).
- GPC gel permeation chromatography
- HFIP hexafluoroisopropanol
- the melting point of the polyamide resin is, for example, 150°C or higher (eg, 155 to 350°C), preferably 160°C or higher (eg, 165 to 300°C), and more preferably 170°C or higher (eg, 175 to 270°C).
- the melting point can be measured using, for example, a differential scanning calorimeter (DSC). More specifically, first, about 5 mg of a sample for measuring the melting point is prepared, and two containers made of metal (for example, aluminum) with the same shape and weight are prepared. Next, the sample is placed in one of the two containers, and the other container is left empty. Then, from the DSC curve obtained when the container containing the sample and the empty container as a reference were set in the DSC and the sample was heated at a heating rate of 10°C/min while flowing nitrogen gas. The melting point can be determined. Note that the melting point can be determined by performing differential scanning calorimetry twice on the same sample, and is determined as the peak value of the second DSC curve.
- DSC differential scanning calorimeter
- the glass transition temperature (Tg) of the polyamide resin is preferably 30°C to 160°C.
- the glass transition temperature (Tg) means the midpoint glass transition temperature measured using a differential scanning calorimeter (DSC).
- the midpoint glass transition temperature can be determined based on the method described in JIS K7121-1987 "Method for Measuring Plastic Transition Temperature.” That is, first, about 5 mg of a sample for measuring the midpoint glass transition temperature is prepared, and two containers made of metal (for example, aluminum) of the same shape and weight are prepared. Next, the sample is placed in one of the two containers, and the other container is left empty. Then, from the DSC curve obtained when the container containing the sample and the empty container as a reference were set in the DSC and the sample was heated at a heating rate of 10°C/min while flowing nitrogen gas. The midpoint glass transition temperature can be determined.
- the crystallinity of the polyamide resin is preferably 80% or less (eg, 1 to 75%), more preferably 50% or less (eg, 10 to 50%).
- the resin particles preferably contain polyamide resin in an amount of 50% by weight or more, more preferably 60 to 99% by weight, even more preferably 70 to 95% by weight.
- the polyolefin resin is a resin containing an olefin as a structural unit.
- the olefin include ⁇ -olefin, ethylene, 2-butene, isoprene, and 2-pentene.
- the ⁇ -olefin include ⁇ -olefins having 3 to 20 carbon atoms, and specifically, propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-Nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 3- Methyl-1-butene, 3-methyl-1-pentene, 3-ethyl-1-pentene, 4-methyl-1-
- the polyolefin resin has a second functional group that can react with the first functional group of the polyamide resin.
- the second functional group include a carboxy group, an amino group, a carboxylic acid anhydride group, an epoxy group, an isocyanate group, and a carbodiimide group.
- the polyolefin resin may have the epoxy group by having a glycidyl group.
- the melting point of the polyolefin resin is, for example, 30 to 200°C, preferably 35 to 175°C, and more preferably 40 to 160°C.
- the resin particles preferably contain the polyamide resin and the polyolefin resin in a total amount of 80 to 100% by weight, more preferably 90 to 100% by weight, and even more preferably 95 to 100% by weight.
- the resin particles preferably contain the polyolefin resin in an amount of 0.5 to 50% by weight, more preferably 1 to 40% by weight, and still more preferably 5 to 30% by weight.
- the resin particles may further contain an additive.
- the resin composition for resin particles may further contain an additive.
- the additives include stabilizers, colorants, dispersants, preservatives, antioxidants, antifoaming agents, and the like.
- the additives may be used alone or in combination of two or more.
- the total content of the additives is, for example, 10 parts by weight or less (for example, 0.01 to 10 parts by weight) based on 100 parts by weight of the polyamide resin and the polyolefin resin.
- the median diameter of the resin particles can be selected from a range of, for example, 2 ⁇ m or more (for example, 3 to 40 ⁇ m), preferably 4 ⁇ m or more (for example, 5 to 40 ⁇ m), more preferably 6 ⁇ m or more (for example, 7 to 35 ⁇ m), and even more preferably 8 ⁇ m. or more (for example, 9 to 30 ⁇ m), particularly preferably 10 ⁇ m or more (for example, 11 to 30 ⁇ m).
- the median diameter of the resin particles means a value measured by dispersing the resin particles in water and using a laser diffraction/scattering particle size distribution analyzer.
- the median diameter of the resin particles means the volume-based median diameter of the resin particles.
- the median diameter of the resin particles means the median diameter of the resin particles as primary particles.
- the resin particles may have a matrix-domain structure (also referred to as a "sea-island structure") including a matrix and domains, the matrix may contain the polyamide resin, and the domains may contain the polyolefin resin. preferable.
- a plurality of the domains are dispersed in the matrix.
- the matrix of the resin particles contains the polyamide resin, it becomes easy to fully exhibit the effect of improving the toughness of the cured product by the resin particles containing the polyamide resin.
- domains containing polyolefin resin are dispersed in the matrix, it becomes easier to contain a large amount of polyolefin resin in the resin particles.
- the matrix contains the first resin means that "the first resin is contained in the matrix in a larger amount than in the domain.”
- the domain contains the second resin means "the second resin is contained in the domain in a larger amount than in the matrix”.
- the resin particles have a matrix-domain structure including a matrix and a domain, and the matrix contains the first resin and the domain contains the second resin as follows. You can check it like this. First, a resin particle is cut to obtain a cross section. Next, the cross section is etched with toluene. Then, the etched cross section is observed with a scanning electron microscope (SEM) to confirm the presence or absence of a matrix-domain structure (matrix: the first resin, domain: the second resin). In addition, in the cross section, the part where the resin particle is etched with toluene and has a hole is the part where the polyolefin resin was.
- SEM scanning electron microscope
- the average particle size of the domain is preferably 1/3 or less of the average particle size of the resin particles, more preferably 1/4 or less of the average particle size of the resin particles, and is more preferably 1/4 or less of the average particle size of the resin particles. It is even more preferably 1/5 or less, still more preferably 1/8 or less of the average particle size of the resin particles, and particularly preferably 1/10 or less of the average particle size of the resin particles. Further, the average particle diameter of the domain is, for example, 1/2000 of the average particle diameter of the resin particles.
- the specific gravity of the resin composition for resin particles is preferably less than 1.3, more preferably 0.80 to 1.25, even more preferably 0.85 to 1.20.
- the specific gravity of the resin composition for resin particles can be determined as follows. First, a dumbbell test piece specified by ISO is produced by injection molding from the resin composition for resin particles. Then, using the dumbbell test piece, the specific gravity of the resin composition for resin particles is measured according to method A (underwater displacement method) of JIS K7112:1999.
- the sphericity of the resin particles is preferably 95% or more and 100% or less, more preferably 97% or more and 100% or less, and even more preferably 99% or more and 100% or less.
- the sphericity of particles can be measured by the following method. That is, the particles are observed with a scanning electron microscope (SEM), the major axis and the minor axis of 30 randomly selected particles are measured, and the minor axis/long axis ratio of each particle is determined. Then, the arithmetic mean value of the short axis/long axis ratio is determined, and this arithmetic mean value is taken as the sphericity of the particle. Note that the closer the sphericity of the particles is to 100%, the more true the particles can be determined to be.
- thermosetting resin composition according to the present embodiment preferably contains the thermosetting resin and the resin particles in a total amount of 50 to 99% by weight, more preferably 80 to 97% by weight.
- the resin particles are preferably 1 to 30 parts by weight, more preferably 3 to 25 parts by weight, and more preferably 1 to 30 parts by weight, based on 100 parts by weight of the thermosetting resin. Contains 5 to 20 parts by weight.
- Method for manufacturing resin particles examples include a freeze pulverization method, a chemical pulverization method, a polymerization method, a forced emulsification method, a laser method, and the like.
- a forced emulsification method is preferred.
- the polyamide resin, the polyolefin resin, and an aqueous medium incompatible with the polyamide resin and the polyolefin resin are melt-kneaded by heating to obtain a melt-kneaded product (A); , the resin particles are obtained by performing a step (B) of cooling the melt-kneaded product and a step (C) of removing the aqueous medium from the cooled melt-kneaded product with a hydrophilic solvent or water.
- the resin particles may be obtained by performing a step (D) of drying the melt-kneaded product using a dehumidifying dryer or the like after the step (C), if necessary.
- the resin particles may be obtained by performing step (E) of classifying the melt-kneaded material.
- the aqueous medium used in the step (A) is selected depending on the type of the polyamide resin and the polyolefin resin.
- the aqueous medium include heat-melting saccharides, water-soluble polymers, and the like.
- the heat-melting saccharides include oligosaccharides (eg, sucrose, maltotriose, etc.), sugar alcohols (eg, xylitol, erythritol, sorbitol, mannitol, etc.), and the like.
- water-soluble polymer examples include water-soluble synthetic polymers (eg, polyethylene glycol, polyvinyl alcohol, sodium polyacrylate, polyacrylamide, etc.), polysaccharides (eg, starch, methylcellulose, etc.), and the like.
- water-soluble synthetic polymers eg, polyethylene glycol, polyvinyl alcohol, sodium polyacrylate, polyacrylamide, etc.
- polysaccharides eg, starch, methylcellulose, etc.
- aqueous medium can be used alone or in combination of two or more.
- polyethylene glycol is preferable from the viewpoint that the resin particles can be easily adjusted to an appropriate particle size.
- the aqueous medium is, for example, 10 to 100 parts by weight, preferably 20 to 100 parts by weight, and more preferably 30 to 100 parts by weight, based on a total of 100 parts by weight of the polyamide resin and the polyolefin resin. Parts by weight.
- the volume ratio of the aqueous medium is, for example, 50% by volume or more (eg, 50 to 90% by volume) with respect to the total volume of the aqueous medium, the polyamide resin, and the polyolefin resin.
- the temperature during melt-kneading in the step (A) may be a temperature higher than the melting point or softening point of the polyamide resin and a temperature higher than the melting point or softening point of the polyolefin resin, for example, 190°C or higher (e.g. 190°C or higher). to 350°C), preferably 200 to 320°C, more preferably 210 to 300°C.
- the melt-kneaded product may be naturally cooled or the melt-kneaded product may be forcedly cooled, but from the viewpoint of productivity, it is preferable to forcibly cool the melt-kneaded product.
- the cooling rate of the melt-kneaded material is preferably, for example, 1° C./min or more (eg, 1 to 10° C./min).
- hydrophilic solvent used in the step (C) examples include alcohol (such as ethanol), water-soluble ketones (such as acetone), and the like.
- the thermosetting resin composition according to this embodiment may include reinforcing fibers. That is, the cured product obtained by thermosetting the thermosetting resin composition according to this embodiment may be fiber reinforced plastic (FRP).
- FRP fiber reinforced plastic
- the reinforcing fibers include carbon fibers, glass fibers, aramid fibers, boron fibers, polyparaphenylene benzobis oxazole (PBO) fibers, polyethylene fibers, alumina fibers, and silicon carbide fibers.
- the reinforcing fibers are preferably carbon fibers. That is, the cured product is preferably carbon fiber reinforced plastic (CFRP).
- the reinforcing fibers may be monofilaments or multifilaments.
- the fineness of the single fibers of the reinforcing fibers is preferably 0.2 to 2.0 dtex, more preferably 0.4 to 1.8 dtex.
- the number of filaments in the fiber is preferably 2,500 to 50,000.
- the reinforcing fibers may be continuous fibers or may be discontinuous. When higher mechanical properties are required for the cured product, continuous fibers are preferred as the reinforcing fibers.
- the continuous fibers may be included in the thermosetting resin composition according to the present embodiment in the form of, for example, a unidirectional base material, knitted fabric, woven fabric, tow, or roving.
- the reinforcing fibers in a discontinuous form may be included in the thermosetting resin composition according to the present embodiment, for example, in the form of a nonwoven fabric or chopped yarn.
- thermosetting resin composition according to the present embodiment preferably contains the reinforcing fibers in an amount of 1 to 50 parts by weight, more preferably 5 to 30 parts by weight, based on 100 parts by weight of the thermosetting resin.
- thermosetting resin composition according to this embodiment may contain a monofunctional epoxy compound.
- monofunctional epoxy compound include monoglycidyl ether, alkene oxide (eg, octylene oxide, styrene oxide, etc.).
- the monoglycidyl ethers include alkyl glycidyl ethers (e.g., 2-ethylhexyl glycidyl ether, etc.), alkenyl glycidyl ethers (e.g., allyl glycidyl ether, etc.), aryl glycidyl ethers (e.g., phenyl glycidyl ether, etc.), and the like. Can be mentioned.
- the ratio of the weight of the epoxy resin to the weight of the monofunctional epoxy compound is, for example, 99/1 to 50/50, preferably 97/3 to 60/40. , more preferably from 95/5 to 70/30.
- thermosetting resin composition may include a curing agent.
- the curing agent can be appropriately selected depending on the type of the thermosetting resin.
- examples of the curing agent include amine curing agents, phenolic resin curing agents, acid anhydride curing agents, polymercaptan curing agents, and latent curing agents. .
- amine curing agent examples include aromatic amine curing agents, aliphatic amine curing agents, imidazoles, salts of imidazoles, and alicyclic amine curing agents.
- aromatic amine curing agent examples include polyaminoarenes, polyamino-alkylarenes, poly(aminoalkyl)arenes, poly(aminoaryl)alkanes, poly(amino-alkylaryl)alkanes, and bis(aminoarylalkyl)arenes. , di(aminoaryl)ethers (e.g., diaminodiphenyl ether, etc.), di(aminoaryloxy)arenes (e.g., 1,3-bis(3-aminophenoxy)benzene, etc.), di(aminoaryl)sulfones (e.g., diamino diphenyl sulfone, etc.).
- di(aminoaryl)ethers e.g., diaminodiphenyl ether, etc.
- di(aminoaryloxy)arenes e.g., 1,3-bis(3-aminophenoxy)benzene,
- polyaminoarene examples include diaminoarene (eg, paraphenylenediamine, metaphenylenediamine, etc.).
- polyamino-alkylarene examples include diamino-alkylarene (eg, diethyltoluenediamine, etc.).
- poly(aminoalkyl)arenes examples include di(aminoalkyl)arenes (eg, xylylene diamine, etc.).
- poly(aminoaryl)alkanes examples include di(aminoaryl)alkanes (eg, diaminodiphenylmethane, etc.).
- poly(amino-alkylaryl)alkanes examples include di(amino-alkylaryl)alkanes (eg, 4,4'-methylenebis(2-ethyl-6-methylaniline), etc.).
- bis(aminoarylalkyl)arene examples include 1,3-bis[2-(4-aminophenyl)-2-propyl)]benzene, 1,4-bis[2-(4-aminophenyl)- 2-propyl)]benzene and the like.
- aliphatic amine curing agent examples include ethylenediamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, diethylaminopropylamine, and the like.
- alicyclic amine curing agent examples include menzendiamine, isophoronediamine, bis(4-amino-3-methylcyclohexyl)methane, 3,9-bis(3-aminopropyl)-2,4,8 , 10-tetraoxaspiro[5.5]undecane, norbornanediamine, and the like.
- Examples of the imidazoles include alkylimidazole and arylimidazole.
- Examples of the alkylimidazole include 2-methylimidazole, 2-phenylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, and the like.
- Examples of the arylimidazole include 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, and 1-benzyl-2-phenylimidazole.
- salts of imidazoles include salts of imidazoles and formic acid, salts of imidazoles and phenol, salts of imidazoles and phenol novolak, salts of imidazoles and carbonic acid, and the like.
- phenolic resin curing agent examples include novolac resin, cresol novolac resin, and the like.
- Examples of the acid anhydride curing agent include aliphatic dicarboxylic anhydrides, alicyclic dicarboxylic anhydrides, aromatic dicarboxylic anhydrides, and the like.
- Examples of the aliphatic dicarboxylic anhydride include dodecenyl succinic anhydride.
- Examples of the alicyclic dicarboxylic anhydride include tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, and the like.
- Examples of the aromatic dicarboxylic anhydride include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenonetetracarboxylic anhydride, and the like.
- latent curing agent examples include boron trifluoride-amine complex, dicyandiamide, and carboxylic acid hydrazide.
- the curing agents may be used alone or in combination of two or more. Note that the curing agent may also act as a curing accelerator. As the curing agent, an amine curing agent (for example, an aromatic amine curing agent) is preferable.
- an amine curing agent for example, an aromatic amine curing agent
- the content ratio of the curing agent can be appropriately selected depending on the type of thermosetting resin (epoxy equivalent, etc.) and the type of curing agent, but for example, it is 0.1 to 300 parts by weight per 100 parts by weight of the thermosetting resin. Parts by weight, preferably 1 to 250 parts by weight, more preferably 3 to 200 parts by weight (for example, 4 to 150 parts by weight), particularly preferably 5 to 100 parts by weight.
- the thermosetting resin composition according to this embodiment may include a curing accelerator.
- the curing accelerator can be appropriately selected depending on the type of the thermosetting resin.
- Examples of the curing accelerator when the thermosetting resin is an epoxy resin include phosphines, amines, and salts of amines.
- Examples of the phosphines include ethylphosphine, propylphosphine, trialkylphosphine, phenylphosphine, and triphenylphosphine.
- the amines include secondary to tertiary amines.
- secondary to tertiary amines examples include triethylamine, piperidine, benzyldimethylamine, triethanolamine, dimethylaminoethanol, triethylenediamine, tris(dimethylaminomethyl)phenol, and N,N-dimethylpiperazine.
- the curing accelerators may be used alone or in combination of two or more.
- the content ratio of the curing accelerator is, for example, 0.01 to 100 parts by weight, preferably 0.05 to 50 parts by weight, and more preferably 1 to 30 parts by weight, based on 100 parts by weight of the thermosetting resin.
- thermosetting resin composition according to the present embodiment may further contain at least one of a thermoplastic resin and an additive as another component, if necessary.
- thermoplastic resin examples include acrylic resin, polyolefin resin (such as polypropylene), polyamide resin, polyester resin, polycarbonate resin, polyphenylene ether resin, polyphenylene sulfide resin, polysulfone resin, polyether ketone resin, and polyether ether ketone.
- examples include resin, polyimide resin, polyetherimide resin, and the like.
- polyester resin include aromatic polyester resins (eg, polyethylene terephthalate, etc.).
- additives examples include non-fibrous fillers, stabilizers, colorants, dispersants, preservatives, antioxidants, antifoaming agents, and the like.
- the content ratio of other components is, for example, 10 parts by weight or less (for example, 0.01 to 10 parts by weight) based on 100 parts by weight of the thermosetting resin.
- the cured product according to this embodiment is a cured product obtained by thermosetting the thermosetting resin composition according to this embodiment.
- the shape of the cured product according to this embodiment may be a one-dimensional shape (such as a rod shape), a two-dimensional shape (such as a sheet shape), or a three-dimensional shape.
- thermosetting resin composition comprising a thermosetting resin and resin particles, The resin particles contain a polyamide resin and a polyolefin resin, A thermosetting resin composition, wherein the content of the polyamide resin in the resin particles is 50% by weight or more.
- thermosetting resin composition in which the cured product has high toughness and the resin particles hardly absorb water.
- This mechanism is thought to be due to the following.
- polyolefin resin is a resin with excellent flexibility
- the flexibility of the resin particles increases when the resin particles contain the polyolefin resin, and when a force is applied to the cured product from the outside, the resin particles absorb the force. It is thought that it becomes easier to disperse, and as a result, the toughness of the cured product becomes higher.
- polyolefin resin is a resin that does not easily absorb moisture, it is thought that the resin particles become particles that do not easily absorb moisture by containing the polyolefin resin.
- the polyamide resin has a first functional group
- the thermosetting resin composition according to item 1 wherein the polyolefin resin has a second functional group capable of reacting with the first functional group.
- the dispersibility of the polyolefin resin in the resin particles is excellent.
- thermosetting resin according to item 2 wherein the second functional group has at least one functional group selected from a carboxy group, an amino group, a carboxylic acid anhydride group, an epoxy group, an isocyanate group, and a carbodiimide group. Resin composition.
- thermosetting resin composition according to any one of items 1 to 3, wherein the thermosetting resin contains an epoxy resin.
- thermosetting resin composition according to any one of items 1 to 4, which contains 1 to 30 parts by weight of the resin particles based on 100 parts by weight of the thermosetting resin.
- the resin particles are formed of a resin composition for resin particles containing the polyamide resin and the polyolefin resin, The thermosetting resin composition according to any one of items 1 to 5, wherein the resin composition for resin particles has a specific gravity of less than 1.3.
- thermosetting resin composition according to any one of items 1 to 6, wherein the polyamide resin includes an alicyclic polyamide resin.
- Polyamide resin Polyamide 12 (PA12): “L1901” manufactured by Daicel-Evonik Polyamide 1010 (PA1010): “DS22” manufactured by Daicel-Evonik Alicyclic polyamide resin (alicyclic PA): “Trogamide (registered trademark) CX7323” manufactured by Daicel-Evonik Alicyclic polyamide resin (alicyclic PA): “Trogamide (registered trademark) CX9704” manufactured by Daicel-Evonik
- Polyolefin resin Polyolefin resin made by modifying a copolymer of ethylene and 1-butene with maleic anhydride: "Tafmer (registered trademark) MH5010” manufactured by Mitsui Chemicals Polyolefin resin made by modifying a copolymer of ethylene and 1-butene with maleic anhydride: "Tafmer (registered trademark) MH5040” manufactured by Mitsui Chemicals Polyolefin resin made by modifying polypropylene with maleic anhydride: "Admer (registered trademark) GF500” manufactured by Mitsui Chemicals
- Polyamide elastomer “Vestamide (registered trademark) EX9200” manufactured by Daicel-Evonik
- thermosetting resin Epoxy resin: "jER828” manufactured by Mitsubishi Chemical Corporation
- Example A-1 95 parts by weight of polyamide 12, 5 parts by weight of polyolefin resin (MH5010), and polyethylene glycol as an aqueous solvent were melt-kneaded by heating in an extruder and extruded through a die of the extruder to obtain a melt-kneaded product.
- the melt-kneaded material was forcibly cooled using a spot cooler.
- the precursor particles remaining on the glass filter were washed with water.
- the precursor particles were dried at 90° C. for 24 hours using a dehumidifying dryer to obtain resin particles.
- thermosetting resin composition (resin particles: 14.4% by weight).
- thermosetting resin composition (resin particles: 20% by weight) was obtained in the same manner as in Example A-1, except that the blending ratio of resin particles was as shown in Table 1 below.
- FIG. 1 shows an SEM photograph of a cross section of the resin particles in Example C-1 (in the cross section, the resin particles were etched with toluene, and the portions with holes are the portions where the polyolefin resin was).
- the saturated water content of the resin composition for resin particles constituting the resin particles was measured by the following method. First, a square test piece (100 mm x 100 mm x 2 mm) was prepared by injection molding from the resin composition for resin particles constituting the resin particles. Then, the square test piece was allowed to absorb water using method A (immersion in 23°C water) of JIS K7209:2000 (ISO62:1999) "Plastics - How to determine water absorption rate", and the saturated water content was measured. The results are shown in Table 1 below.
- thermosetting resin composition was poured into a mold (47 mm (length) x 12 mm (width) x 4 mm (thickness)).
- thermosetting resin composition was heated at 175° C. until the thermosetting resin composition was sufficiently thermoset to obtain a cured product having pre-crack.
- a convex portion corresponding to the pre-crack was formed on the inner surface of the mold.
- the plane strain fracture toughness (K IC ) of the cured product was determined in accordance with ASTM D5045. The results are shown in Table 1 below.
- Example B-1 which is within the scope of the present disclosure and in which the polyamide resin is polyamide 1010 (PA1010), Comparative Example B-1 in which the resin particles are made only of polyamide 1010 (PA1010) Compared to the above, the saturated water absorption rate of the resin composition for resin particles constituting the resin particles was low, and the plane strain fracture toughness (K IC ) of the cured product was high.
- K IC plane strain fracture toughness
- Example C-1 which is within the scope of the present disclosure and in which the polyamide resin is an alicyclic polyamide resin (alicyclic PA) (CX7323), the resin particles are alicyclic polyamide resin (alicyclic PA) (CX7323).
- the saturated water absorption rate of the resin composition for resin particles constituting the resin particles is lower, and the cured product has a lower plane strain fracture. Toughness (K IC ) was high.
- Example D-1 which is within the scope of the present disclosure and in which the polyamide resin is a cycloaliphatic polyamide resin (cycloaliphatic PA) (CX9704), the resin particles are cycloaliphatic.
- Comparative Example D-1 consisting only of formula polyamide resin (alicyclic PA) (CX9704)
- the saturated water absorption rate of the resin composition for resin particles constituting the resin particles is lower, and the cured product has a lower plane strain fracture.
- Toughness (K IC ) was high.
- Example D-1 the plane strain fracture toughness (K IC ) of the cured product was higher than in Comparative Example D-2, which used silica filler instead of polyolefin resin. .
- thermosetting resin composition in which the cured product has high toughness and the resin particles do not easily absorb moisture.
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Abstract
Description
ここで、前記熱硬化性樹脂組成物に前記樹脂粒子を含ませる際には、硬化物に含まれるボイドを抑制するためや、樹脂粒子と熱硬化性樹脂とを混合しやすくするために、樹脂粒子に含まれる水分を抑制することが求められ得る。
すなわち、水分を吸収し難い樹脂粒子が求められ得る。
前記樹脂粒子が、ポリアミド樹脂、及び、ポリオレフィン樹脂を含有し、
前記樹脂粒子における前記ポリアミド樹脂の含有量が、50重量%以上である、熱硬化性樹脂組成物に関する。
また、本明細書に開示された各々の態様は、本明細書に開示された他のいかなる特徴とも組み合わせることができる。
本実施形態に係る熱硬化性樹脂組成物は、熱硬化性樹脂、及び、樹脂粒子を含む。
前記樹脂粒子は、ポリアミド樹脂、及び、ポリオレフィン樹脂を含有する。
前記樹脂粒子における前記ポリアミド樹脂の含有量が、50重量%以上である。
前記熱硬化性樹脂としては、例えば、エポキシ樹脂、フェノール樹脂、不飽和ポリエステル樹脂、ビニルエステル樹脂、アクリル樹脂、尿素樹脂、メラミン樹脂、アニリン樹脂、ポリイミド樹脂、ビスマレイミド樹脂などが挙げられる。これらの熱硬化性樹脂は、単独で又は2種以上組み合わせてもよい。
エポキシ樹脂とポリアミド樹脂とは相溶性に優れることから、前記熱硬化性樹脂がエポキシ樹脂を含むことにより、前記ポリアミド樹脂を含む樹脂粒子が前記エポキシ樹脂中に分散されやすくなり、前記樹脂粒子による靭性の向上の効果が発揮されやすくなる。
前記ビスフェノール類としては、例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、臭素化ビスフェノール型エポキシ樹脂などが挙げられる。
前記ビスフェノール類のアルキレンオキシド付加体においては、ビスフェノール類のヒドロキシル基1モルに対するアルキレンオキシドの付加モル数は、例えば1モル以上(例えば1~20モル)、好ましくは1~15モル、さらに好ましくは1~10モルである。
前記ナフタレン骨格を有するグリシジルエーテルとしては、例えば、ジ(グリシジルオキシ)ナフタレン、ビス[2,7-ジ(グリシジルオキシ)ナフチル]メタン等が挙げられる。
前記ジ(グリシジルオキシ)ナフタレンとしては、例えば、1,5-ジ(グリシジルオキシ)ナフタレンなどが挙げられる。
前記C2-10アルカンジオールジグリシジルエーテルとしては、例えば、ブタンジオールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、1,6-ヘキサンジオールジグリシジルエーテル等が挙げられる。
前記ポリC2-4アルカンジオールジグリシジルエーテルとしては、例えば、ポリプロピレングリコールジグリシジルエーテル等が挙げられる。
前記ポリオールとしては、例えば、アルカントリオール、アルカンテトラオール、アルカンペンタオール、アルカンヘキサオール等が挙げられる。前記アルカントリオールとしては、C3-10アルカントリオール等が挙げられる。前記アルカンテトラオールとしては、C3-10アルカンテトラオール等が挙げられる。
前記グリシジルポリエーテルとしては、ジグリシジルエーテル、トリグリシジルエーテル、テトラグリシジルエーテル、ペンタグリシジルエーテル、ヘキサグリシジルエーテル等が挙げられる。
前記ポリオールのグリシジルポリエーテルとしては、例えば、トリメチロールプロパンジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、グリセリンジグリシジルエーテル、グリセリントリグリシジルエーテル等が挙げられる。
前記ジカルボン酸としては、例えば、芳香族ジカルボン酸、芳香族ジカルボン酸の水添物等が挙げられる。
前記芳香族ジカルボン酸としては、例えば、テレフタル酸、イソフタル酸、フタル酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸等が挙げられる。
これらのエポキシ樹脂のうち、強度などの点で、芳香族骨格を有するエポキシ樹脂が好ましく、ビスフェノール型エポキシ樹脂が特に好ましい。
前記フェノール樹脂としては、例えば、ノボラック型フェノール樹脂、レゾール型フェノール樹脂、ポリオキシスチレン樹脂などが挙げられる。
前記レゾール型フェノール樹脂は、フェノール類とアルデヒド類と縮合物である。前記レゾール型フェノール樹脂は、例えば、フェノール類とアルデヒド類とをアルカリ性触媒の存在下で縮合重合させることで得られる。
前記クレゾールとしては、o-クレゾール、m-クレゾール、p-クレゾールが挙げられる。
前記トリメチルフェノールとしては、2,3,5-トリメチルフェノール等が挙げられる。
前記キシレノールとしては、2,3-キシレノール、2,4-キシレノール、2,5-キシレノール、3,4-キシレノール、3,5-キシレノール等が挙げられる。
前記ヒドロキシベンズアルデヒドとしては、o-ヒドロキシベンズアルデヒド、m-ヒドロキシベンズアルデヒド、p-ヒドロキシベンズアルデヒドが挙げられる。
前記樹脂粒子は、ポリアミド樹脂、及び、ポリオレフィン樹脂を含有する樹脂粒子用樹脂組成物で形成されている。
前記ポリアミド樹脂は、ホモポリアミド樹脂又はコポリアミド樹脂であってもよい。
該第1の官能基としては、アミノ基、カルボキシ基、酸無水物基、エポキシ基、イソシアネート基、カルボジイミド基等が挙げられる。
前記アミノ基としては、「-NH2」、「-NHR」が挙げられる。
Rは、アルキル基である。Rとしては、例えば、メチル基、エチル基、プロピル基などが挙げられる。
前記酸無水物基としては、カルボン酸無水物基などが挙げられる。
前記脂環式ポリアミド樹脂としては、ジアミン成分及びジカルボン酸成分として、脂環式ジアミン成分及び/又は脂環式ジカルボン酸成分と共に、前記例示の脂肪族ジアミン成分及び/又は脂肪族ジカルボン酸成分を含む脂環式ポリアミド樹脂が好ましい。このような脂環式ポリアミド樹脂は、透明性が高く、いわゆる透明ポリアミド樹脂として知られている。
前記ジアミノシクロアルカンとしては、例えば、ジアミノシクロヘキサン等が挙げられる。前記ジアミノシクロアルカンは、ジアミノC5-10シクロアルカンが好ましい。
前記ビス(アミノシクロアルキル)アルカンとしては、例えば、ビス(4-アミノシクロヘキシル)メタン、ビス(4-アミノ-3-メチルシクロヘキシル)メタン、2,2-ビス(4’-アミノシクロヘキシル)プロパン等が挙げられる。前記ビス(アミノシクロアルキル)アルカンは、ビス(アミノC5-8シクロアルキル)C1-3アルカンが好ましい。
前記脂環式ジアミン成分は、例えば、アルキル基などの置換基を有していてもよい。
該アルキル基は、好ましくはC1-6アルキル基、より好ましくはC1-4アルキル基、さらに好ましくはC1-2アルキル基(メチル基、エチル基等)である。
前記芳香族ポリアミド樹脂としては、構成単位のジアミン成分及び構成単位のジカルボン酸成分の両方が芳香族成分であるポリアミド樹脂(「全芳香族ポリアミド樹脂」や「アラミド」等とも呼ばれる。)等が挙げられる。
前記芳香族ポリアミド樹脂は、変性ポリアミド樹脂であってもよい。変性ポリアミド樹脂としては、分岐鎖構造を有するポリアミド樹脂等が挙げられる。
前記芳香族ジアミン成分としては、メタキシリレンジアミン等が挙げられる。
前記芳香族ジカルボン酸成分としては、テレフタル酸、イソフタル酸等が挙げられる。また、前記芳香族ジカルボン酸成分は、ダイマー酸等であってもよい。
前記ポリアミド樹脂としては、補強効果が大きい点から、半結晶性ポリアミド樹脂(例えば、脂環式ポリアミド樹脂、脂肪族ポリアミド樹脂等)が好ましい。
なお、本実施形態において、数平均分子量は、ヘキサフルオロイソプロパノール(HFIP)を用いたゲルパーミエーションクロマトグラフィー(GPC)を用い、ポリメチルメタクリレート(PMMA)換算分子量分布より測定されたものをいう。当該GPCにおけるカラムとしては、前記分子量を測定するのに適切なカラムを使用すればよい。
より具体的には、まず、融点を測定するための試料を約5mg用意するとともに、同じ形状で同じ重量の金属(例えば、アルミニウム)製の容器を2つ用意する。
次に、2つの前記容器のうち一方の容器に試料を入れ、他方の容器を空のままとする。
そして、試料を入れた容器と、リファレンスとしての空の容器とをDSCにセットし、窒素ガスを流しながら10℃/minの昇温速度で前記試料を昇温させた際に得られるDSC曲線から融点を求めることができる。
なお、融点は、同一試料に対して2回の示差走査熱量分析を実施して求めることができ、2回目のDSC曲線のピーク値として求められる。
中間点ガラス転移温度は、JIS K7121-1987「プラスチックの転移温度測定方法」に記載されている方法に基づいて求めることができる。
すなわち、まず、中間点ガラス転移温度を測定するための試料を約5mg用意するとともに、同じ形状で同じ重量の金属(例えば、アルミニウム)製の容器を2つ用意する。
次に、2つの前記容器のうち一方の容器に試料を入れ、他方の容器を空のままとする。
そして、試料を入れた容器と、リファレンスとしての空の容器とをDSCにセットし、窒素ガスを流しながら10℃/minの昇温速度で前記試料を昇温させた際に得られるDSC曲線から中間点ガラス転移温度を求めることができる。
本実施形態において、結晶化度は、広角X線回折(WAXD)に基づいて測定できる。
例えば、粉末X線解析ソフトウェア(リガク社製「PDXL Ver2.3.1.0」)を用いて、広角X線回折で得られた回折曲線にフィッティング(方法:FP法、ピーク形状:対数正規分布、バックグラウンド精密化:なし)を行うことにより、結晶回折ピーク、非晶質ハローを分離し、下記式から結晶化度(%)を求めることができる。
結晶化度 = [結晶回折ピークの積分強度総和(cps・deg)]/[結晶回折ピーク及び非晶質ハローの積分強度総和(cps・deg)]×100%
前記オレフィンとしては、α-オレフィン、エチレン、2-ブテン、イソプレン、2-ペンテンなどが挙げられる。
前記α-オレフィンとしては、炭素原子数が3~20であるα-オレフィンが挙げられ、具体的には、プロピレン、1-ブテン、1-ペンテン、1-ヘキセン、1-ヘプテン、1-オクテン、1-ノネン、1-デセン、1-ウンデセン、1-ドデセン、1-トリデセン、1-テトラデセン、1-ペンタデセン、1-ヘキサデセン、1-ヘプタデセン、1-オクタデセン、1-ノナデセン、1-エイコセン、3-メチル-1-ブテン、3-メチル-1-ペンテン、3-エチル-1-ペンテン、4-メチル-1-ペンテン、4-メチル-1-ヘキセン、4,4-ジメチル-1-ヘキセン、4,4-ジメチル-1-ペンテン、4-エチル-1-ヘキセン、3-エチル-1-ヘキセン、9-メチル-1-デセン、11-メチル-1-ドデセン、12-エチル-1-テトラデセン等が挙げられる。
前記ポリオレフィン樹脂は、単独重合体であってもよく、また、共重合体であってもよい。
前記第2の官能基としては、カルボキシ基、アミノ基、カルボン酸無水物基、エポキシ基、イソシアネート基、カルボジイミド基などが挙げられる。
前記ポリオレフィン樹脂は、グリシジル基を有することにより前記エポキシ基を有してもよい。
前記添加剤としては、例えば、安定剤、着色剤、分散剤、防腐剤、抗酸化剤、消泡剤などが挙げられる。
前記添加剤は、単独で又は2種以上組み合わせてもよい。
前記添加剤の含有割合の合計は、前記ポリアミド樹脂と前記ポリオレフィン樹脂との合計100重量部に対して、例えば10重量部以下(例えば0.01~10重量部)である。
前記樹脂粒子のメジアン径は、樹脂粒子を水に分散させて、レーザー回折/散乱式粒度分布測定装置によって測定した値を意味する。また、前記樹脂粒子のメジアン径は、樹脂粒子の体積基準のメジアン径を意味する。
さらに、前記樹脂粒子のメジアン径は、1次粒子の樹脂粒子のメジアン径を意味する。
前記マトリックス-ドメイン構造を有する樹脂粒子では、複数個の前記ドメインが前記マトリックスに分散している。
前記樹脂粒子において前記マトリックスが前記ポリアミド樹脂を含有することにより、ポリアミド樹脂を含む樹脂粒子による硬化物の靭性の向上効果を十分に発揮しやすくなる。
また、ポリオレフィン樹脂を含むドメインが前記マトリックスに分散していることにより、ポリオレフィン樹脂を樹脂粒子に多く含ませやすくなる。
「前記マトリックスは、前記第1の樹脂を含有する」とは、「前記第1の樹脂が前記ドメインよりも前記マトリックスに多く含まれる」ことを意味する。また、「前記ドメインは、前記第2の樹脂を含有する」とは、「前記第2の樹脂が前記マトリックスよりも前記ドメインに多く含まれる」ことを意味する。
まず、樹脂粒子を切断して断面を得る。
次に、該断面をトルエンでエッチングする。
そして、エッチングした断面を走査電子顕微鏡(SEM)で観察し、マトリックス-ドメイン構造(マトリックス:前記第1の樹脂、ドメイン:前記第2の樹脂)の有無を確認する。
なお、断面において樹脂粒子がトルエンでエッチングされて穴が開いている部分は、ポリオレフィン樹脂があった部分である。
前記樹脂粒子用樹脂組成物の比重は、以下のようにして求めることができる。
まず、前記樹脂粒子用樹脂組成物から射出成形によりISOに規定されているダンベル試験片を作製する。
そして、該ダンベル試験片を用いて、JIS K7112:1999のA法(水中置換法)に準拠して、前記樹脂粒子用樹脂組成物の比重を測定する。
なお、本実施形態において、粒子の真球度は、次の方法により測定できる。すなわち、走査型電子顕微鏡(SEM)で粒子を観察し、無作為に選択した30個の粒子の長径と短径を測定し、各粒子の短径/長径比を求める。そして、短径/長径比の算術平均値を求め、この算術平均値を粒子の真球度とする。なお、粒子の真球度が100%に近いほど、粒子が真球であると判断できる。
樹脂粒子の製造方法としては、冷凍粉砕法、化学粉砕法、重合法、強制乳化法、レーザー法等が挙げられる。
樹脂粒子の製造方法としては、強制乳化法が好ましい。
前記強制乳化法では、必要に応じて、前記工程(C)後に、前記溶融混練物を除湿乾燥機等で乾燥させる工程(D)を実施することにより、前記樹脂粒子を得てもよい。
また、所望の粒径の樹脂粒子を得るために、前記強制乳化法では、前記工程(C)後に(前記工程(D)を実施する場合には、前記工程(D)後又は前記工程(D)前に)、前記溶融混練物を分級する工程(E)を実施することにより、前記樹脂粒子を得てもよい。
前記水性媒体としては、例えば、熱溶融性の糖類、水溶性高分子などが挙げられる。
前記熱溶融性の糖類としては、例えば、オリゴ糖(例えば、スクロース、マルトトリオースなど)、糖アルコール(例えば、キシリトール、エリスリトール、ソルビトール、マンニトールなど)などが挙げられる。
前記水溶性高分子としては、例えば、水溶性合成高分子(例えば、ポリエチレングリコール、ポリビニルアルコール、ポリアクリル酸ナトリウム、ポリアクリルアミドなど)、多糖類(例えば、デンプン、メチルセルロースなど)などが挙げられる。
これらの水性媒体は、単独で又は二種以上組み合わせて使用できる。
前記水性媒体としては、樹脂粒子を適度な粒径に調整し易いという観点から、ポリエチレングリコールが好ましい。
水性媒体の体積割合は、水性媒体、前記ポリアミド樹脂、及び、前記ポリオレフィン樹脂の総体積に対して、例えば50体積%以上(例えば50~90体積%)である。
溶融混練物の冷却速度は、例えば、1℃/分以上(例えば1~10℃/分)が好ましい。
本実施形態に係る熱硬化性樹脂組成物は、強化繊維を含んでもよい。すなわち、本実施形態に係る熱硬化性樹脂組成物が熱硬化された硬化物は、繊維強化プラスチック(FRP)であってもよい。
前記強化繊維としては、例えば、炭素繊維、ガラス繊維、アラミド繊維、ボロン繊維、ポリパラフェニレン・ベンゾビス・オキサゾール(PBO)繊維、ポリエチレン繊維、アルミナ繊維、炭化ケイ素繊維などが挙げられる。
前記強化繊維としては、炭素繊維が好ましい。すなわち、前記硬化物は、炭素繊維強化プラスチック(CFRP)であることが好ましい。
前記強化繊維の単繊維の繊度は、好ましくは0.2~2.0dtex、より好ましくは0.4~1.8dtexである。
より高い力学特性が硬化物に求められる場合には、前記強化繊維としては、連続繊維が好ましい。
連続繊維は、例えば、一方向基材、編み物、織物、トウ、又は、ロービング等となって、本実施形態に係る熱硬化性樹脂組成物に含まれていてもよい。
不連続の形態の強化繊維は、例えば、不織布、又は、チョップド糸等となって、本実施形態に係る熱硬化性樹脂組成物に含まれていてもよい。
前記熱硬化性樹脂がエポキシ樹脂を含む場合には、本実施形態に係る熱硬化性樹脂組成物は、単官能性のエポキシ化合物を含んでもよい。
前記単官能性のエポキシ化合物としては、モノグリシジルエーテル、アルケンオキシド(例えば、オクチレンオキシド、スチレンオキシドなど)等が挙げられる。
前記モノグリシジルエーテルとしては、例えば、アルキルグリシジルエーテル(例えば、2-エチルへキシルグリシジルエーテルなど)、アルケニルグリシジルエーテル(例えば、アリルグリシジルエーテルなど)、アリールグリシジルエーテル(例えば、フェニルグリシジルエーテルなど)等が挙げられる。
本実施形態に係る熱硬化性樹脂組成物において、前記単官能性のエポキシ化合物の重量に対する前記エポキシ樹脂の重量の比は、例えば99/1~50/50、好ましくは97/3~60/40、さらに好ましくは95/5~70/30である。
本実施形態に係る熱硬化性樹脂組成物は、硬化剤を含んでもよい。
前記硬化剤としては、前記熱硬化性樹脂の種類に応じて適宜選択できる。
熱硬化性樹脂がエポキシ樹脂である場合の硬化剤としては、例えば、アミン系硬化剤、フェノール樹脂系硬化剤、酸無水物系硬化剤、ポリメルカプタン系硬化剤、潜在性硬化剤などが挙げられる。
前記ポリアミノアレーンとしては、例えば、ジアミノアレーン(例えば、パラフェニレンジアミン、メタフェニレンジアミン等)等が挙げられる。
前記ポリアミノ-アルキルアレーンとしては、例えば、ジアミノ-アルキルアレーン(例えば、ジエチルトルエンジアミン等)等が挙げられる。
前記ポリ(アミノアルキル)アレーンとしては、例えば、ジ(アミノアルキル)アレーン(例えば、キシリレンジアミン等)等が挙げられる。
前記ポリ(アミノアリール)アルカンとしては、例えば、ジ(アミノアリール)アルカン(例えば、ジアミノジフェニルメタン等)等が挙げられる。
前記ポリ(アミノ-アルキルアリール)アルカンとしては、例えば、ジ(アミノ-アルキルアリール)アルカン(例えば、4,4’-メチレンビス(2-エチル-6-メチルアニリン)等)等が挙げられる。
前記ビス(アミノアリールアルキル)アレーンとしては、例えば、1,3-ビス[2-(4-アミノフェニル)-2-プロピル)]ベンゼン、1,4-ビス[2-(4-アミノフェニル)-2-プロピル)]ベンゼン等が挙げられる。
前記アルキルイミダゾールとしては、例えば、2-メチルイミダゾール、2-フェニルイミダゾール、2-へプタデシルイミダゾール、2-エチル-4-メチルイミダゾール等が挙げられる。
前記アリールイミダゾールとしては、例えば、2-フェニルイミダゾール、2-フェニル-4-メチルイミダゾール、2-フェニル-4-メチル-5-ヒドロキシメチルイミダゾール、1-ベンジル-2-フェニルイミダゾール等が挙げられる。
前記脂肪族ジカルボン酸無水物としては、例えば、ドデセニル無水コハク酸などが挙げられる。
前記脂環式ジカルボン酸無水物としては、例えば、テトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸などが挙げられる。
前記芳香族ジカルボン酸無水物としては、例えば、無水フタル酸、無水トリメリット酸、無水ピロメリット酸、ベンゾフェノンテトラカルボン酸無水物などが挙げられる。
前記硬化剤としては、アミン系硬化剤(例えば、芳香族アミン系硬化剤)が好ましい。
本実施形態に係る熱硬化性樹脂組成物は、硬化促進剤を含んでもよい。
前記硬化促進剤としては、前記熱硬化性樹脂の種類に応じて適宜選択できる。
熱硬化性樹脂がエポキシ樹脂である場合の硬化促進剤としては、例えば、ホスフィン類、アミン類、アミン類の塩などが挙げられる。
前記ホスフィン類としては、例えば、エチルホスフィン、プロピルホスフィン、トリアルキルホスフィン、フェニルホスフィン、トリフェニルホスフィンなどが挙げられる。
前記アミン類としては、例えば、第2~3級アミン類等が挙げられる。
第2~3級アミン類としては、例えば、トリエチルアミン、ピペリジン、ベンジルジメチルアミン、トリエタノールアミン、ジメチルアミノエタノール、トリエチレンジアミン、トリス(ジメチルアミノメチル)フェノール、N,N-ジメチルピペラジン等が挙げられる。
硬化促進剤は、単独で又は2種以上組み合わせてもよい。
本実施形態に係る熱硬化性樹脂組成物は、必要に応じて、他の成分として、熱可塑性樹脂及び添加剤の少なくとも何れか一をさらに含んでいてもよい。
前記ポリエステル樹脂としては、例えば、芳香族ポリエステル樹脂(例えば、ポリエチレンテレフタレートなど)などが挙げられる。
本実施形態に係る硬化物の形状は、一次元的形状(棒状など)、二次元的形状(シート状など)、又は、三次元的形状であってもよい。
以下の項目のそれぞれは、好ましい実施形態の開示である。
熱硬化性樹脂、及び、樹脂粒子を含む、熱硬化性樹脂組成物であって、
前記樹脂粒子が、ポリアミド樹脂、及び、ポリオレフィン樹脂を含有し、
前記樹脂粒子における前記ポリアミド樹脂の含有量が、50重量%以上である、熱硬化性樹脂組成物。
このメカニズムは、以下によるものと考えられる。
すなわち、ポリオレフィン樹脂は柔軟性に優れる樹脂であることから、樹脂粒子がポリオレフィン樹脂を含有することにより樹脂粒子の柔軟性が高まり、硬化物に外部から力が掛かった際に、樹脂粒子により力が分散されやすくなり、その結果、硬化物の靭性が高くなると考えられる。
また、ポリオレフィン樹脂は水分を吸収し難い樹脂であることから、樹脂粒子は、ポリオレフィン樹脂を含有することにより水分を吸収し難い粒子になると考えられる。
前記ポリアミド樹脂は、第1の官能基を有し、
前記ポリオレフィン樹脂は、前記第1の官能基と反応可能な第2の官能基を有する、項目1に記載の熱硬化性樹脂組成物。
前記第2の官能基は、カルボキシ基、アミノ基、カルボン酸無水物基、エポキシ基、イソシアネート基、及び、カルボジイミド基から選ばれる少なくとも1種の官能基を有する、項目2に記載の熱硬化性樹脂組成物。
前記熱硬化性樹脂がエポキシ樹脂を含む、項目1~3の何れかに記載の熱硬化性樹脂組成物。
前記熱硬化性樹脂100重量部に対して、前記樹脂粒子を1~30重量部含む、項目1~4の何れかに記載の熱硬化性樹脂組成物。
前記樹脂粒子は、前記ポリアミド樹脂、及び、前記ポリオレフィン樹脂を含有する樹脂粒子用樹脂組成物で形成されており、
該樹脂粒子用樹脂組成物の比重が1.3未満である、項目1~5の何れかに記載の熱硬化性樹脂組成物。
前記ポリアミド樹脂が脂環式ポリアミド樹脂を含む、項目1~6の何れかに記載の熱硬化性樹脂組成物。
項目1~7の何れかに記載の熱硬化性樹脂組成物が熱硬化された、硬化物。
ポリアミド12(PA12):ダイセル・エボニック社製の「L1901」
ポリアミド1010(PA1010):ダイセル・エボニック社製の「DS22」
脂環式ポリアミド樹脂(脂環式PA):ダイセル・エボニック社製の「トロガミド(登録商標)CX7323」
脂環式ポリアミド樹脂(脂環式PA):ダイセル・エボニック社製の「トロガミド(登録商標)CX9704」
エチレンと1-ブテンとの共重合体を無水マレイン酸で変性したポリオレフィン樹脂:三井化学社製の「タフマー(登録商標)MH5010」
エチレンと1-ブテンとの共重合体を無水マレイン酸で変性したポリオレフィン樹脂:三井化学社製の「タフマー(登録商標)MH5040」
ポリプロピレンを無水マレイン酸で変性したポリオレフィン樹脂:三井化学社製の「アドマー(登録商標)GF500」
ヘキサメチルジシラザンで表面処理されたフュームドシリカ(疎水性フュームドシリカ):アエロジル社製の「RX50」
ポリアミドエラストマー:ダイセル・エボニック社製の「ベスタミド(登録商標)EX9200」
エポキシ樹脂:三菱化学社製の「jER828」
アミン系硬化剤:三菱化学社製の「jERキュアW」
95重量部のポリアミド12と、5重量部のポリオレフィン樹脂(MH5010)と、水性溶媒たるポリエチレングリコールとを押出機で加熱により溶融混練し、押出機のダイから押し出し、溶融混練物を得た。
次に、スポットクーラーを用いて前記溶融混練物を強制的に冷却した。
そして、アスピレーターとグラスフィルターとを用いて、前記溶融混練物を濾過しつつ、グラスフィルターに留まった前駆体粒子を水で洗浄した。
次に、除湿乾燥機を用いて前駆体粒子を90℃で24時間乾燥させ、樹脂粒子を得た。
次に、ホットスターラーを用いて、80℃、300rpmの条件下で、前記エポキシ樹脂及び前記樹脂粒子を6時間撹拌することにより混合物を得た。
そして、該混合物を真空容器中で1時間放置することにより、該混合物を脱泡させた。
次に、脱泡した混合物に硬化剤を加えて撹拌および脱泡を行うことにより、熱硬化性樹脂組成物(樹脂粒子:14.4重量%)を得た。
樹脂粒子の配合割合を下記表1のようにしたこと以外は、実施例A-1と同様にして熱硬化性樹脂組成物(樹脂粒子:20重量%)を得た。
実施例C-1における樹脂粒子の断面のSEM写真(断面において樹脂粒子がトルエンでエッチングされており、穴が開いている部分は、ポリオレフィン樹脂があった部分である。)を図1に示す。
樹脂粒子を構成する樹脂粒子用樹脂組成物の比重は、上述した方法で測定した。
樹脂粒子用樹脂組成物の比重を下記表1に示す。
前記樹脂粒子を構成する樹脂粒子用樹脂組成物の飽和水分量は、以下の方法で測定した。
まず、前記樹脂粒子を構成する樹脂粒子用樹脂組成物から射出成形により正方形状試験片(100mm×100mm×2mm)を用意した。
そして、JIS K7209:2000(ISO62:1999)「プラスチック-吸水率の求め方」のA法(23℃の水に浸漬)で正方形状試験片に水分を吸収させ、飽和水分量を測定した。
下記表1に結果を示す。
まず、熱硬化性樹脂組成物を金型(47mm(長さ)×12mm(幅)×4mm(厚み))に流し込んだ。
次に、熱硬化性樹脂組成物が十分に熱硬化するまで熱硬化性樹脂組成物を175℃で加熱し、予亀裂を有する硬化物を得た。なお、該硬化物に予亀裂を設けるべく、前記金型の内面には、前記予亀裂に対応する凸部が形成されていた。
そして、予亀裂を有する硬化物を用いて、硬化物の平面ひずみ破壊靭性(KIC)をASTM D5045に準拠して求めた。
下記表1に結果を示す。
表1に示すように、本開示の範囲内であり、且つ、ポリアミド樹脂がポリアミド12(PA12)である実施例A-1~A-6では、樹脂粒子がポリアミド12(PA12)のみからなる比較例A-1に比べて、樹脂粒子を構成する樹脂粒子用樹脂組成物の飽和吸水率が低く、且つ、硬化物の平面ひずみ破壊靭性(KIC)が高かった。
また、表1に示すように、前記実施例A-1~A-6では、ポリオレフィン樹脂の代わりにポリアミドエラストマーを用いた比較例A-2に比べて、硬化物の平面ひずみ破壊靭性(KIC)が高かった。
表1に示すように、本開示の範囲内であり、且つ、ポリアミド樹脂がポリアミド1010(PA1010)である実施例B-1では、樹脂粒子がポリアミド1010(PA1010)のみからなる比較例B-1に比べて、樹脂粒子を構成する樹脂粒子用樹脂組成物の飽和吸水率が低く、且つ、硬化物の平面ひずみ破壊靭性(KIC)が高かった。
また、表1に示すように、本開示の範囲内であり、且つ、ポリアミド樹脂が脂環式ポリアミド樹脂(脂環式PA)(CX7323)である実施例C-1では、樹脂粒子が脂環式ポリアミド樹脂(脂環式PA)(CX7323)のみからなる比較例C-1に比べて、樹脂粒子を構成する樹脂粒子用樹脂組成物の飽和吸水率が低く、且つ、硬化物の平面ひずみ破壊靭性(KIC)が高かった。
さらに、表1に示すように、本開示の範囲内であり、且つ、ポリアミド樹脂が脂環式ポリアミド樹脂(脂環式PA)(CX9704)である実施例D-1では、樹脂粒子が脂環式ポリアミド樹脂(脂環式PA)(CX9704)のみからなる比較例D-1に比べて、樹脂粒子を構成する樹脂粒子用樹脂組成物の飽和吸水率が低く、且つ、硬化物の平面ひずみ破壊靭性(KIC)が高かった。
また、表1に示すように、前記実施例D-1では、ポリオレフィン樹脂の代わりにシリカフィラーを用いた比較例D-2に比べて、硬化物の平面ひずみ破壊靭性(KIC)が高かった。
Claims (8)
- 熱硬化性樹脂、及び、樹脂粒子を含む、熱硬化性樹脂組成物であって、
前記樹脂粒子が、ポリアミド樹脂、及び、ポリオレフィン樹脂を含有し、
前記樹脂粒子における前記ポリアミド樹脂の含有量が、50重量%以上である、熱硬化性樹脂組成物。 - 前記ポリアミド樹脂は、第1の官能基を有し、
前記ポリオレフィン樹脂は、前記第1の官能基と反応可能な第2の官能基を有する、請求項1に記載の熱硬化性樹脂組成物。 - 前記第2の官能基は、カルボキシ基、アミノ基、カルボン酸無水物基、エポキシ基、イソシアネート基、及び、カルボジイミド基から選ばれる少なくとも1種の官能基を有する、請求項2に記載の熱硬化性樹脂組成物。
- 前記熱硬化性樹脂がエポキシ樹脂を含む、請求項1~3の何れか1項に記載の熱硬化性樹脂組成物。
- 前記熱硬化性樹脂100重量部に対して、前記樹脂粒子を1~30重量部含む、請求項1~3の何れか1項に記載の熱硬化性樹脂組成物。
- 前記樹脂粒子は、前記ポリアミド樹脂、及び、前記ポリオレフィン樹脂を含有する樹脂粒子用樹脂組成物で形成されており、
該樹脂粒子用樹脂組成物の比重が1.3未満である、請求項1~3の何れか1項に記載の熱硬化性樹脂組成物。 - 前記ポリアミド樹脂が脂環式ポリアミド樹脂を含む、請求項1~3の何れか1項に記載の熱硬化性樹脂組成物。
- 請求項1~3の何れか1項に記載の熱硬化性樹脂組成物が熱硬化された、硬化物。
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