JPWO2019013025A1 - 成形品およびその製造方法 - Google Patents
成形品およびその製造方法 Download PDFInfo
- Publication number
- JPWO2019013025A1 JPWO2019013025A1 JP2018539446A JP2018539446A JPWO2019013025A1 JP WO2019013025 A1 JPWO2019013025 A1 JP WO2019013025A1 JP 2018539446 A JP2018539446 A JP 2018539446A JP 2018539446 A JP2018539446 A JP 2018539446A JP WO2019013025 A1 JPWO2019013025 A1 JP WO2019013025A1
- Authority
- JP
- Japan
- Prior art keywords
- component
- fiber
- resin composition
- composite material
- molded article
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000011248 coating agent Substances 0.000 claims abstract description 70
- 238000000576 coating method Methods 0.000 claims abstract description 70
- 239000000463 material Substances 0.000 claims abstract description 67
- 239000003733 fiber-reinforced composite Substances 0.000 claims abstract description 54
- -1 Thiol compound Chemical class 0.000 claims abstract description 38
- 239000011342 resin composition Substances 0.000 claims abstract description 34
- 238000000465 moulding Methods 0.000 claims abstract description 33
- 239000004844 aliphatic epoxy resin Substances 0.000 claims abstract description 20
- 150000004714 phosphonium salts Chemical group 0.000 claims abstract description 13
- 239000003822 epoxy resin Substances 0.000 claims description 56
- 229920000647 polyepoxide Polymers 0.000 claims description 56
- 239000012783 reinforcing fiber Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 150000003573 thiols Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 7
- 239000004917 carbon fiber Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 description 66
- 239000011347 resin Substances 0.000 description 66
- 239000000203 mixture Substances 0.000 description 42
- 239000003795 chemical substances by application Substances 0.000 description 38
- 239000007788 liquid Substances 0.000 description 35
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 21
- 238000005259 measurement Methods 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002344 surface layer Substances 0.000 description 10
- 238000002845 discoloration Methods 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 6
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 5
- 239000002759 woven fabric Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 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
- 230000008859 change Effects 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 3
- LABQKWYHWCYABU-UHFFFAOYSA-N 4-(3-sulfanylbutanoyloxy)butyl 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCCCCOC(=O)CC(C)S LABQKWYHWCYABU-UHFFFAOYSA-N 0.000 description 3
- 102100027123 55 kDa erythrocyte membrane protein Human genes 0.000 description 3
- 239000004412 Bulk moulding compound Substances 0.000 description 3
- 101001057956 Homo sapiens 55 kDa erythrocyte membrane protein Proteins 0.000 description 3
- 239000003677 Sheet moulding compound Substances 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 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 3
- 239000010410 layer Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 2
- 102100029647 Apoptosis-associated speck-like protein containing a CARD Human genes 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- 101000728679 Homo sapiens Apoptosis-associated speck-like protein containing a CARD Proteins 0.000 description 2
- 101000707471 Homo sapiens Serine incorporator 3 Proteins 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- LYMYULOYDUWMOP-UHFFFAOYSA-M diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane;tetrabutylphosphanium Chemical compound CCOP([S-])(=S)OCC.CCCC[P+](CCCC)(CCCC)CCCC LYMYULOYDUWMOP-UHFFFAOYSA-M 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229940064639 minipress Drugs 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 2
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 2
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- RLZMYANQLOCZOB-UHFFFAOYSA-M tributyl(methyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](C)(CCCC)CCCC RLZMYANQLOCZOB-UHFFFAOYSA-M 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- FWYKRJUVEOBFGH-UHFFFAOYSA-M triphenyl(prop-2-enyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 FWYKRJUVEOBFGH-UHFFFAOYSA-M 0.000 description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 2
- FWBSWSPGFNAXPP-UHFFFAOYSA-M (2,4-dichlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].ClC1=CC(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FWBSWSPGFNAXPP-UHFFFAOYSA-M 0.000 description 1
- VRAAQIWOSHYDHE-UHFFFAOYSA-M (2-chlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].ClC1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VRAAQIWOSHYDHE-UHFFFAOYSA-M 0.000 description 1
- VJVZPTPOYCJFNI-UHFFFAOYSA-M (2-ethoxy-2-oxoethyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)OCC)C1=CC=CC=C1 VJVZPTPOYCJFNI-UHFFFAOYSA-M 0.000 description 1
- FKKZGQXMWVGPMH-UHFFFAOYSA-N (2-hydroxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].OC1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FKKZGQXMWVGPMH-UHFFFAOYSA-N 0.000 description 1
- VCWBQLMDSMSVRL-UHFFFAOYSA-M (2-methoxy-2-oxoethyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)OC)C1=CC=CC=C1 VCWBQLMDSMSVRL-UHFFFAOYSA-M 0.000 description 1
- BLALYSCMLUQKSG-UHFFFAOYSA-M (3,4-dimethoxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=C(OC)C(OC)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BLALYSCMLUQKSG-UHFFFAOYSA-M 0.000 description 1
- NNJRPZZMNBNRFJ-UHFFFAOYSA-N (3-ethoxy-3-oxo-2-phenylpropyl)azanium;chloride Chemical compound Cl.CCOC(=O)C(CN)C1=CC=CC=C1 NNJRPZZMNBNRFJ-UHFFFAOYSA-N 0.000 description 1
- FQJYKXVQABPCRA-UHFFFAOYSA-M (4-bromophenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(Br)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FQJYKXVQABPCRA-UHFFFAOYSA-M 0.000 description 1
- RAHOAHBOOHXRDY-UHFFFAOYSA-M (4-chlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RAHOAHBOOHXRDY-UHFFFAOYSA-M 0.000 description 1
- MZBKKJRCQNVENM-UHFFFAOYSA-M (4-ethoxyphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(OCC)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MZBKKJRCQNVENM-UHFFFAOYSA-M 0.000 description 1
- IPJPTPFIJLFWLP-UHFFFAOYSA-M (4-nitrophenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC([N+](=O)[O-])=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IPJPTPFIJLFWLP-UHFFFAOYSA-M 0.000 description 1
- IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 description 1
- PAEWNKLGPBBWNM-UHFFFAOYSA-N 1,3,5-tris[2-(3-sulfanylbutoxy)ethyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(S)CCOCCN1C(=O)N(CCOCCC(C)S)C(=O)N(CCOCCC(C)S)C1=O PAEWNKLGPBBWNM-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- JTINZFQXZLCHNS-UHFFFAOYSA-N 2,2-bis(oxiran-2-ylmethoxymethyl)butan-1-ol Chemical compound C1OC1COCC(CO)(CC)COCC1CO1 JTINZFQXZLCHNS-UHFFFAOYSA-N 0.000 description 1
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- XETDBHNHTOJWPZ-UHFFFAOYSA-M 2-(1,3-dioxan-2-yl)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].O1CCCOC1CC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XETDBHNHTOJWPZ-UHFFFAOYSA-M 0.000 description 1
- YIIHEMGEQQWSMA-UHFFFAOYSA-M 2-(dimethylamino)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCN(C)C)C1=CC=CC=C1 YIIHEMGEQQWSMA-UHFFFAOYSA-M 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- PULOARGYCVHSDH-UHFFFAOYSA-N 2-amino-3,4,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1OC1CC1=C(CC2OC2)C(N)=C(O)C=C1CC1CO1 PULOARGYCVHSDH-UHFFFAOYSA-N 0.000 description 1
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 description 1
- XAMZZEBAJZJERT-UHFFFAOYSA-M 2-oxopropyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)C)C1=CC=CC=C1 XAMZZEBAJZJERT-UHFFFAOYSA-M 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
- NKVJKVMGJABKHV-UHFFFAOYSA-N 3-carboxypropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC(=O)O)C1=CC=CC=C1 NKVJKVMGJABKHV-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- UHUUGQDYCYKQTC-UHFFFAOYSA-N 4-[2,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CC(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UHUUGQDYCYKQTC-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- AVMUCZNGCWTULU-UHFFFAOYSA-N 4-bromo-3-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Br)C(Cl)=C1 AVMUCZNGCWTULU-UHFFFAOYSA-N 0.000 description 1
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 1
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GIGIQZILMFVZQM-UHFFFAOYSA-M [2-(1,3-dioxan-2-yl)phenyl]-methyl-diphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C(=CC=CC=1)C1OCCCO1)(C)C1=CC=CC=C1 GIGIQZILMFVZQM-UHFFFAOYSA-M 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical group NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- ZGLFRTJDWWKIAK-UHFFFAOYSA-M [2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZGLFRTJDWWKIAK-UHFFFAOYSA-M 0.000 description 1
- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 description 1
- ARXLXPBUIFYJAM-UHFFFAOYSA-N [Cl-].C1(=CC=CC=C1)[PH3+].[Cl-].[Cl-].[Cl-].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+] Chemical compound [Cl-].C1(=CC=CC=C1)[PH3+].[Cl-].[Cl-].[Cl-].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+].C1(=CC=CC=C1)[PH3+] ARXLXPBUIFYJAM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UBGVHKXCHHMPRK-UHFFFAOYSA-N benzotriazol-2-ide;tetrabutylphosphanium Chemical compound C1=CC=CC2=N[N-]N=C21.CCCC[P+](CCCC)(CCCC)CCCC UBGVHKXCHHMPRK-UHFFFAOYSA-N 0.000 description 1
- WTEPWWCRWNCUNA-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 WTEPWWCRWNCUNA-UHFFFAOYSA-M 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- YFTMLUSIDVFTKU-UHFFFAOYSA-M bromomethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CBr)C1=CC=CC=C1 YFTMLUSIDVFTKU-UHFFFAOYSA-M 0.000 description 1
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- SXYFAZGVNNYGJQ-UHFFFAOYSA-M chloromethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCl)C1=CC=CC=C1 SXYFAZGVNNYGJQ-UHFFFAOYSA-M 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- DOMOOBQQQGXLGU-UHFFFAOYSA-N cyanoiminomethylideneazanide;trihexyl(tetradecyl)phosphanium Chemical compound [N-]=C=NC#N.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC DOMOOBQQQGXLGU-UHFFFAOYSA-N 0.000 description 1
- ARPLQAMUUDIHIT-UHFFFAOYSA-M cyanomethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC#N)C1=CC=CC=C1 ARPLQAMUUDIHIT-UHFFFAOYSA-M 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LSDYBCGXPCFFNM-UHFFFAOYSA-M dimethyl phosphate;tributyl(methyl)phosphanium Chemical compound COP([O-])(=O)OC.CCCC[P+](C)(CCCC)CCCC LSDYBCGXPCFFNM-UHFFFAOYSA-M 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VRAYVWUMBAJVGH-UHFFFAOYSA-M ethenyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=C)C1=CC=CC=C1 VRAYVWUMBAJVGH-UHFFFAOYSA-M 0.000 description 1
- TUDUDQJRUPFUMA-UHFFFAOYSA-M ethyl(trioctyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CC)(CCCCCCCC)CCCCCCCC TUDUDQJRUPFUMA-UHFFFAOYSA-M 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WCZSOHSGMBVYFW-UHFFFAOYSA-M heptyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCC)C1=CC=CC=C1 WCZSOHSGMBVYFW-UHFFFAOYSA-M 0.000 description 1
- PWDFZWZPWFYFTC-UHFFFAOYSA-M hexyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCC)C1=CC=CC=C1 PWDFZWZPWFYFTC-UHFFFAOYSA-M 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- QRPRIOOKPZSVFN-UHFFFAOYSA-M methyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 QRPRIOOKPZSVFN-UHFFFAOYSA-M 0.000 description 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 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
- MOYSMPXSEXYEJV-UHFFFAOYSA-M naphthalen-1-ylmethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC2=CC=CC=C2C=1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MOYSMPXSEXYEJV-UHFFFAOYSA-M 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- VAUKWMSXUKODHR-UHFFFAOYSA-M pentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC)C1=CC=CC=C1 VAUKWMSXUKODHR-UHFFFAOYSA-M 0.000 description 1
- AEHDSYHVTDJGDN-UHFFFAOYSA-M phenacyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1C(=O)C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEHDSYHVTDJGDN-UHFFFAOYSA-M 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- ZOMVKCHODRHQEV-UHFFFAOYSA-M tetraethylphosphanium;hydroxide Chemical compound [OH-].CC[P+](CC)(CC)CC ZOMVKCHODRHQEV-UHFFFAOYSA-M 0.000 description 1
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- JBKMIQBGAFQGNO-UHFFFAOYSA-M tributyl(1,3-dioxan-2-ylmethyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CC1OCCCO1 JBKMIQBGAFQGNO-UHFFFAOYSA-M 0.000 description 1
- JCHWNYYARSRCKZ-UHFFFAOYSA-M tributyl(cyanomethyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC#N JCHWNYYARSRCKZ-UHFFFAOYSA-M 0.000 description 1
- ABJGUZZWSKMTEI-UHFFFAOYSA-M tributyl(dodecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC ABJGUZZWSKMTEI-UHFFFAOYSA-M 0.000 description 1
- UJHVZVXYELCZLX-UHFFFAOYSA-M tributyl(dodecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC UJHVZVXYELCZLX-UHFFFAOYSA-M 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- UJMLRSWRUXXZEW-UHFFFAOYSA-M tributyl(octyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCC)(CCCC)CCCC UJMLRSWRUXXZEW-UHFFFAOYSA-M 0.000 description 1
- QCLVFLIIJODTJU-UHFFFAOYSA-N triethyl(octyl)phosphanium Chemical compound CCCCCCCC[P+](CC)(CC)CC QCLVFLIIJODTJU-UHFFFAOYSA-N 0.000 description 1
- XUNCOSCFGRBTRX-UHFFFAOYSA-M triethyl(octyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CC)(CC)CC XUNCOSCFGRBTRX-UHFFFAOYSA-M 0.000 description 1
- RGXJWHBYXNYHML-UHFFFAOYSA-N triethyl(pentyl)phosphanium Chemical compound CCCCC[P+](CC)(CC)CC RGXJWHBYXNYHML-UHFFFAOYSA-N 0.000 description 1
- HESQQIOZXPMZKL-UHFFFAOYSA-M triethyl(pentyl)phosphanium;bromide Chemical compound [Br-].CCCCC[P+](CC)(CC)CC HESQQIOZXPMZKL-UHFFFAOYSA-M 0.000 description 1
- JXLXUMBTJJLQGB-UHFFFAOYSA-M triphenyl(1-trimethylsilylpropan-2-yl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C[Si](C)(C)C)C)C1=CC=CC=C1 JXLXUMBTJJLQGB-UHFFFAOYSA-M 0.000 description 1
- NEUMNYXEDIPGJD-UHFFFAOYSA-M triphenyl(2-trimethylsilylethoxymethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COCC[Si](C)(C)C)C1=CC=CC=C1 NEUMNYXEDIPGJD-UHFFFAOYSA-M 0.000 description 1
- NXZYPOSEOPBJMW-UHFFFAOYSA-M triphenyl(2-trimethylsilylethyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC[Si](C)(C)C)C1=CC=CC=C1 NXZYPOSEOPBJMW-UHFFFAOYSA-M 0.000 description 1
- AFZDAWIXETXKRE-UHFFFAOYSA-M triphenyl(prop-2-ynyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC#C)C1=CC=CC=C1 AFZDAWIXETXKRE-UHFFFAOYSA-M 0.000 description 1
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
- FUMBGFNGBMYHGH-UHFFFAOYSA-M triphenyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCCCC)C1=CC=CC=C1 FUMBGFNGBMYHGH-UHFFFAOYSA-M 0.000 description 1
- PJQVALHFZIYJMT-UHFFFAOYSA-M triphenyl(thiophen-2-ylmethyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CS1 PJQVALHFZIYJMT-UHFFFAOYSA-M 0.000 description 1
- APIBROGXENTUGB-ZUQRMPMESA-M triphenyl-[(e)-3-phenylprop-2-enyl]phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 APIBROGXENTUGB-ZUQRMPMESA-M 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
- B29C70/28—Shaping operations therefor
- B29C70/40—Shaping or impregnating by compression not applied
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
- B29C70/28—Shaping operations therefor
- B29C70/54—Component parts, details or accessories; Auxiliary operations, e.g. feeding or storage of prepregs or SMC after impregnation or during ageing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/042—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2363/02—Polyglycidyl ethers of bis-phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2463/02—Polyglycidyl ethers of bis-phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Composite Materials (AREA)
- Mechanical Engineering (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
成分[A]:脂肪族エポキシ樹脂
成分[B]:チオール化合物
成分[C]:第四級ホスホニウム塩
ここで、上記被膜は、繊維強化複合材料の表面の一部が被膜となったものではなく、別途、表面に形成されたものである。
成分[A]:脂肪族エポキシ樹脂
成分[B]:チオール化合物
成分[C]:第四級ホスホニウム塩
[成分[A]:脂肪族エポキシ樹脂]
本発明で用いられる成分[A]は、脂肪族エポキシ樹脂である。脂肪族エポキシ樹脂とは、水酸基を複数有するアルコールから得られる脂肪族グリシジルエーテルを意味する。
[その他のエポキシ樹脂]
本発明で用いられる樹脂組成物は上記成分[A]の他に、本出願の特性を損なわない範囲で必要に応じて、他のエポキシ樹脂を含んでも良い。成分[A]以外のエポキシ樹脂の例としては、例えば、水酸基を複数有するフェノールから得られる芳香族グリシジルエーテル、アミンから得られるグリシジルアミンを有するエポキシ樹脂、およびカルボキシル基を複数有するカルボン酸から得られるグリシジルエステルなどが好ましく挙げられる。
本発明で用いられる成分[B]はチオール化合物であり、より具体的には、成分[A](脂肪族エポキシ樹脂)のエポキシ基と反応可能なチオール基を一分子中に2個以上有する化合物を指し、エポキシ樹脂の硬化剤として作用するものが好ましい。
本発明で用いられる成分[C]は、第四級ホスホニウム塩である。これらは速硬化性発現のための硬化促進剤として作用するため好ましい。
[被膜用樹脂組成物のキュアインデックス]
本発明に係る樹脂組成物は、定温保持下での誘電測定で求められるキュアインデックスが90%となる時間をt90としたとき、t90が次の式(式1)を満たす特定温度Tを有することが好ましい。
・t90≦30・・・・・(式1)
(t90は、温度Tにおける測定開始からキュアインデックスが90%に到達する時間(分)を表す)。
・キュアインデックス={log(αt)−log(αmin)}/{log(αmax)−log(αmin)}×100・・・(式2)
・キュアインデックス:(単位:%)
・αt:時間tにおけるイオン粘度(単位:Ω・cm)
・αmin:イオン粘度の最小値(単位:Ω・cm)
・αmax:イオン粘度の最大値(単位:Ω・cm)。
本発明の被膜用樹脂組成物は、成分[A]を含む主剤液と、成分[B]を主成分(なお、ここでいう主成分とは、硬化剤液中において質量基準で最大量の成分であることを意味する。)として含む硬化剤液とを、それぞれ前記した配合量で配合しておき、使用直前に前記した配合量となるように、主剤液と硬化剤液を混合して得られる。前記した成分[C]は、主剤液、硬化剤液のどちらに配合することができるが、硬化剤液に含まれることがより好ましい態様である。
本発明に用いる繊維強化複合材料において、強化繊維とともに複合材料を形成するマトリクス樹脂の種類としては、熱可塑性樹脂、熱硬化性樹脂のいずれをも適宜適用することができる。マトリクス樹脂として、不飽和ポリエステル樹脂、エポキシ樹脂、フェノール樹脂、ポリウレタン樹脂などの熱硬化性樹脂を用いると、機械的特性に優れる繊維強化樹脂成形品を得られるため、好ましい。また、耐熱性の観点から、マトリクス樹脂のガラス転移温度は100℃以上であることが好ましい。
各実施例の被膜用樹脂組成物を得るために、次の樹脂原料を用いた。表1中のエポキシ樹脂組成物の含有割合の単位は、特に断らない限り「質量部」を意味する。
1.エポキシ樹脂
・“リカレジン”(登録商標)HBE−100(新日本理化(株)製):水添ビスフェノールA型エポキシ樹脂、エポキシ当量215
・“リカレジン”(登録商標)DME−100(新日本理化(株)製):1,4−シクロヘキサンジメタノールのジグリシジルエーテル、エポキシ当量158
・“エポトート”(登録商標)YD−128(新日鉄住金化学(株)製):ビスフェノールA型エポキシ樹脂、エポキシ当量189
2.チオール化合物
・PEMP(SC有機化学(株)製):ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)
・“カレンズMT”(登録商標)NR1(昭和電工(株)製):1,3,5−トリス(3−メルカプトブチリルオキシエチル)−1,3,5−トリアジン―2,4,6(1H,3H,5H)−トリオン
・“カレンズMT”(登録商標)PE1(昭和電工(株)製):ペンタエリスリトールテトラキス(3−メルカプトブチレート)
3.第四級ホスホニウム塩
・エチルトリフェニルホスホニウムブロミド(東京化成工業(株)製)
・“ヒシコーリン”(登録商標)PX−4ET(日本化学工業(株)製):テトラブチルホスホニウムo,o−ジエチルホスホロジチオエート
4.その他物質
・メタキシリレンジアミン(東京化成工業(株)製)
・HN−5500(日立化成(株)製):メチルヘキサヒドロフタル酸無水物
・トリ−p−トリルホスフィン(東京化成工業(株)製)
<被膜用樹脂組成物の調製>
表1に記載した配合比により、エポキシ樹脂を配合し主剤液とした。表1に記載した配合比で、成分[B](チオール化合物)と成分[C](第四級ホスホニウム塩)、その他の物質を配合して硬化剤液とした。これらの主剤液と硬化剤液とを用い、これらを表1に記載した配合比で混合して、エポキシ樹脂組成物を調製した。
ISO 2884−1(1999)における円錐平板型回転粘度計を使用した測定方法に準拠し、被膜用樹脂組成物の混合調製1分後の粘度を測定し、粘度安定性の指標とした。装置には、東機産業(株)製のTVE−33H型を用いた。ここでローターは1゜34’×R24を用い、測定温度は50℃、サンプル量は1cm3とした。
エポキシ樹脂の硬化を追跡するために、誘電測定を行った。誘電測定装置として、Holometrix−Micromet社製のMDE−10キュアモニターを使用した。TMS−1インチ型センサーを下面に埋め込んだプログラマブルミニプレスMP2000の下面に、内径が32mmで、厚さが3mmのバイトン製Oリングを設置し、プレスの温度を50℃に設定し、Oリングの内側にエポキシ樹脂組成物を注ぎプレスを閉じ、エポキシ樹脂組成物のイオン粘度の時間変化を追跡した。誘電測定は、1、10、100、1000および10000Hzの各周波数で行い、付属のソフトウェアを用いて、周波数非依存のイオン粘度の対数Log(α)を得た。
・キュアインデックス={log(αt)−log(αmin)}/{log(αmax)−log(αmin)}×100 ・・・(式2)
・キュアインデックス:(単位:%)
・αt:時間tにおけるイオン粘度(単位:Ω・cm)
・αmin:イオン粘度の最小値(単位:Ω・cm)
・αmax:イオン粘度の最大値(単位:Ω・cm)。
プレス装置下面に、一辺50mmの正方形をくり抜いた、厚さ2mmの銅製スペーサーを設置し、プレスの温度を50℃に設定し、エポキシ樹脂組成物をスペーサーの内側に注ぎ、プレスを閉じた。30分後にプレスを開け、樹脂硬化板を得た。その後、105℃3時間の熱処理を加えた。
上記の樹脂硬化板について着色の有無を判断した。具体的には、樹脂硬化板から切り出した30mm角、厚さ2mmの試験片を使用し、分光測色計(CM−700d、コニカミノルタ(株)製)を用いて、硬化物の色調をL*a*b*表色系で表した。L*a*b*表色系は物質の色を表すのに用いられているもので、L*により明度を表し、a*とb*により色度を表す。ここで、a*は赤方向、−a*は緑方向、b*は黄方向、−b*は青方向を示す。測定条件は波長380〜780nmの範囲において、D65光源、10°視野として、正反射光を含まない条件での分光透過率を測定した。このとき、|a*|≦2であって、かつ|b*|≦5であるものは「着色無し」、それ以外を「着色有り」とした。
繊維強化複合材料には、下記のRTM成形法によって作製したものを用いた。
被膜用金型の温度を50℃に調整し、下型に120mm×60mmにカットした繊維強化複合材料を置き、上型を閉じた後、金型内を真空引きした。その後、表1の配合比に従い、前記したようにして被膜用樹脂組成物を混合調製し、金型内に樹脂を流し込み、30分後に上型を開け、表面に被膜が形成された繊維強化樹脂成形品を取り出した。
表面平滑性の評価は成形品表面のウェーブスキャン(WS)値の確認で行った。自動車用途において、最も表面が良い状態は「クラスA」と呼ばれている。「クラスA」の統一的な基準は定められていないものの、一般に、表面の小さなピッチで出てくる凹凸量を示すショートウェーブ(SW)が20以下、表面の大きなピッチで出てくる凹凸量を示すロングウェーブ(LW)が8以下であることが多い。被膜の形成された繊維強化樹脂成形品の表面を、ウェーブスキャン機器(ウェーブスキャンデュアル)を用いてLW値を5回測定し、その平均値を、表1に記載した。
耐候性は、被膜の形成された成形品をキセノンウェザーメーター(スガ試験機(株)製SX75)中に置き、50日間経過前後の変化で評価した。試験はSAE J2527に基づき実施した。静置前後で、着色や表面のひび割れ・荒れの無かったものを「A」、僅かな変色やひび割れ・荒れのあったものを「B」、著しい変色やひび割れ・荒れのあるものを「C」とした。
表1に示したように、脂肪族エポキシ樹脂「“リカレジン”(登録商標)HBE−100」50質量部と、脂肪族エポキシ樹脂「“リカレジン”(登録商標)DME−100」50質量部からなる主剤液と、チオール化合物「“カレンズMT”(登録商標)NR1」104質量部に第四級ホスホニウム塩「“ヒシコーリン”(登録商標)PX−4ET」3質量部を相溶させた硬化剤液と、からエポキシ樹脂組成物を混合調製した。この被膜用エポキシ樹脂組成物は、50℃の温度で保持しても増粘が低く抑えられ、低粘度状態が維持されていた。また、50℃の温度でのt90で表される脱型可能時間が短いため、硬化被膜を有する繊維強化複合材料の成形において、成形時間の短縮にも効果的であることが分かった。また、この被膜用エポキシ樹脂組成物の硬化物は、着色が無かった。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、良好な表面平滑性を示し、また耐候性評価においても変色など無く良好な耐候性を示した。結果を表1に示す。
チオール化合物「“カレンズMT”(登録商標)NR1」を83部にしたこと以外は、実施例1と同様に実施した。50℃での粘度安定性に優れ、また脱型可能時間が短かった。また、このエポキシ樹脂組成物の硬化物は着色が無かった。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、良好な表面平滑性を示し、また耐候性評価においても変色など無く良好な耐候性を示した。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)HBE−100」100質量部からなる主剤液と、硬化剤液中のチオール化合物「“カレンズMT”(登録商標)PE1」を実施例3は63質量部、実施例4は81質量部としたこと以外は、実施例1と同様に実施した。いずれも、50℃での粘度安定性に優れ、また脱型可能時間が短かった。また、このエポキシ樹脂組成物の硬化物は着色が無かった。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、良好な表面平滑性を示し、また耐候性評価においても変色など無く良好な耐候性を示した。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)DME−100」100質量部からなる主剤液と、硬化剤液をチオール化合物「PEMP」77質量部と、エチルトリフェニルホスホニウムブロミド2.5質量部としたこと以外は、実施例1と同様に実施した。50℃での粘度安定性に優れ、また脱型可能時間が短かった。また、このエポキシ樹脂組成物の硬化物は着色が無かった。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、良好な表面平滑性を示し、また耐候性評価においても変色など無く良好な耐候性を示した。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)HBE−100」90質量部と脂肪族エポキシ樹脂「“リカレジン”(登録商標)DME−100」10質量部からなる主剤液と、硬化剤液にはチオール化合物「“カレンズMT”(登録商標)PE1」71質量部、第四級ホスホニウム塩「“ヒシコーリン”(登録商標)PX−4ET」を実施例6は0.1部、実施例7は10部としたこと以外は、実施例1と同様に実施した。いずれも50℃での粘度安定性に優れ、また脱型可能時間が短かった。また、このエポキシ樹脂組成物の硬化物は着色が無かった。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、良好な表面平滑性を示し、また耐候性評価においても変色など無く良好な耐候性を示した。結果を表1に示す。
主剤液をビスフェノールA型エポキシ樹脂「“エポトート”(登録商標)YD−128」100質量部、硬化剤液のチオール化合物「“カレンズMT”(登録商標)NR1」を100質量部にしたこと以外は、実施例1と同様に実施した。この被膜用エポキシ樹脂組成物は成分[A]を含まないため、この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は実施例に比べて耐候性が劣った。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)HBE−100」100質量部からなる主剤液と、メタキシリレンジアミンを32質量部からなる硬化剤液としたこと以外は、実施例1と同様に実施した。この被膜用エポキシ樹脂組成物は成分[B]、[C]を含まないため、50℃で十分に早く硬化せず、高温にすることで硬化し、硬化物は着色した。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、硬化被膜を高温で成形せざるを得ず、表面平滑性が劣るものであった。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)DME−100」100質量部からなる主剤液と、酸無水物「HN−5500」106質量部とトリ−p−トリルホスフィン5質量部からなる硬化剤液としたこと以外は、実施例1と同様に実施した。この被膜用エポキシ樹脂組成物は成分[B]、[C]を含まないため、50℃で十分に早く硬化せず、高温にすることで硬化した。この被膜用エポキシ樹脂組成物を用いて作製した硬化被膜を有する繊維強化複合材料は、硬化被膜を高温で成形せざるを得ず、表面平滑が劣るものであった。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)HBE−100」100質量部からなる主剤液と、硬化剤液をチオール化合物「PEMP」57質量部としたこと以外は、実施例1と同様に実施した。この被膜用エポキシ樹脂組成物は成分[C]を含まないため、50℃でも高温でも硬化しなかった。結果を表1に示す。
脂肪族エポキシ樹脂「“リカレジン”(登録商標)HBE−100」100質量部からなる主剤液と、硬化剤液をエチルトリフェニルホスホニウムブロミド2.5質量部としたこと以外は、実施例1と同様に実施した。この被膜用エポキシ樹脂組成物は成分[B]を含まないため、50℃でも高温でも硬化しなかった。結果を表1に示す。
Claims (11)
- 繊維強化複合材料の表面に、樹脂組成物が硬化されてなる被膜が形成された成形品であって、
前記樹脂組成物は以下の成分[A]〜[C]を含む、成形品。
成分[A]:脂肪族エポキシ樹脂
成分[B]:チオール化合物
成分[C]:第四級ホスホニウム塩 - 前記樹脂組成物は、成分[C]を、前記成分[A]100質量部に対し、0.1質量部以上15質量部未満含む、請求項1に記載の成形品。
- 前記成分[B]が、2級チオール構造または3級チオール構造を有する、請求項1〜3のいずれかに記載の成形品。
- 前記成分[A]が脂環構造を有する、請求項1〜5のいずれかに記載の成形品。
- 前記成分[A]がシクロヘキサン環を有する、請求項6に記載の成形品。
- 前記成分[A]が水添ビスフェノール型エポキシ樹脂である、請求項1〜7のいずれかに記載の成形品。
- 前記繊維強化複合材料は複数の強化繊維層を有し、
前記強化繊維層の中で被膜と接する強化繊維層の形態が、平織りの強化繊維織物、綾織りの強化繊維織物、繻子織りの強化繊維織物又は一方向性の強化繊維織物から選択される、請求項1〜8のいずれかに記載の成形品。 - 前記繊維強化複合材料が、強化繊維として炭素繊維を含む、請求項1〜9のいずれかに記載の成形品。
- 繊維強化複合材料を成形温度80℃以上300℃以下で成形する工程、及び、
前記繊維強化複合材料の表面にて成分[A]〜[C]を含む樹脂組成物を30℃以上80℃未満で硬化させて被膜とする工程を有する、請求項1〜10のいずれかに記載の成形品の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2017136807 | 2017-07-13 | ||
JP2017136807 | 2017-07-13 | ||
PCT/JP2018/025037 WO2019013025A1 (ja) | 2017-07-13 | 2018-07-02 | 成形品およびその製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2019013025A1 true JPWO2019013025A1 (ja) | 2020-05-07 |
JP7215170B2 JP7215170B2 (ja) | 2023-01-31 |
Family
ID=65001721
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018539446A Active JP7215170B2 (ja) | 2017-07-13 | 2018-07-02 | 自動車の外装部材用成形品およびその製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20200148847A1 (ja) |
EP (1) | EP3653663B1 (ja) |
JP (1) | JP7215170B2 (ja) |
KR (1) | KR20200031064A (ja) |
CN (1) | CN110650997A (ja) |
AU (1) | AU2018300880A1 (ja) |
WO (1) | WO2019013025A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA3029407C (en) * | 2016-06-29 | 2021-05-11 | Dic Corporation | Hollow fiber membrane module sealed with an epoxy resin and a production method therefor |
CN117355557A (zh) * | 2021-05-24 | 2024-01-05 | 东丽精细化工株式会社 | 聚合物组合物、环氧树脂组合物、环氧树脂用固化剂及快速固化型粘接剂 |
CN116218438A (zh) * | 2021-12-02 | 2023-06-06 | 3M创新有限公司 | 单组分环氧粘合剂组合物及其制备方法 |
WO2023157750A1 (ja) * | 2022-02-16 | 2023-08-24 | 株式会社Adeka | 繊維強化プラスチック用樹脂組成物、及び繊維強化プラスチック |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001291757A (ja) * | 2000-02-03 | 2001-10-19 | Nippon Mitsubishi Oil Corp | 加工面を被覆処理したcfrp製搬送用部材およびその処理方法 |
JP2002322588A (ja) * | 2001-04-25 | 2002-11-08 | Nitto Shinko Kk | マスキング材の製造方法及びマスキング材 |
JP2002327041A (ja) * | 2001-02-14 | 2002-11-15 | Toray Ind Inc | 繊維強化複合材料用エポキシ樹脂組成物、プリプレグ及び繊維強化複合材料 |
JP2009197180A (ja) * | 2008-02-25 | 2009-09-03 | Toray Ind Inc | 耐光性エポキシ樹脂組成物およびそれを用いた繊維強化複合材料 |
JP2012077159A (ja) * | 2010-09-30 | 2012-04-19 | Fujifilm Corp | インク組成物、印画物及びその製造方法 |
JP2013133339A (ja) * | 2011-12-22 | 2013-07-08 | Nippon Zeon Co Ltd | エポキシ樹脂組成物、硬化物、透明封止材料及び光半導体装置 |
WO2015107903A1 (ja) * | 2014-01-17 | 2015-07-23 | 東レ株式会社 | 被覆繊維強化樹脂成形品およびその製造方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100371376C (zh) * | 2000-10-19 | 2008-02-27 | 长春人造树脂厂股份有限公司 | 阻燃性环氧树脂组合物及其应用 |
JP2008088212A (ja) | 2006-09-29 | 2008-04-17 | Sekisui Chem Co Ltd | 電子部品用エポキシ組成物、及び、半導体用封止剤 |
JP2009013263A (ja) | 2007-07-03 | 2009-01-22 | Nitto Denko Corp | 光半導体素子封止用エポキシ樹脂組成物およびそれを用いた光半導体装置 |
TWI534171B (zh) | 2007-07-26 | 2016-05-21 | Ajinomoto Kk | 樹脂組成物 |
WO2010137636A1 (ja) | 2009-05-28 | 2010-12-02 | 昭和電工株式会社 | エポキシ樹脂コーティング組成物 |
JP2013209510A (ja) | 2012-03-30 | 2013-10-10 | Dainippon Toryo Co Ltd | 繊維強化樹脂成形体被覆組成物、該被覆組成物を塗装して得られる繊維強化樹脂成形体及び該繊維強化樹脂成形体の製造方法 |
JP2013221091A (ja) * | 2012-04-17 | 2013-10-28 | Showa Denko Kk | エポキシ樹脂組成物 |
-
2018
- 2018-07-02 AU AU2018300880A patent/AU2018300880A1/en not_active Abandoned
- 2018-07-02 WO PCT/JP2018/025037 patent/WO2019013025A1/ja unknown
- 2018-07-02 KR KR1020197024947A patent/KR20200031064A/ko unknown
- 2018-07-02 JP JP2018539446A patent/JP7215170B2/ja active Active
- 2018-07-02 US US16/604,232 patent/US20200148847A1/en not_active Abandoned
- 2018-07-02 EP EP18831141.9A patent/EP3653663B1/en active Active
- 2018-07-02 CN CN201880033859.9A patent/CN110650997A/zh active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001291757A (ja) * | 2000-02-03 | 2001-10-19 | Nippon Mitsubishi Oil Corp | 加工面を被覆処理したcfrp製搬送用部材およびその処理方法 |
JP2002327041A (ja) * | 2001-02-14 | 2002-11-15 | Toray Ind Inc | 繊維強化複合材料用エポキシ樹脂組成物、プリプレグ及び繊維強化複合材料 |
JP2002322588A (ja) * | 2001-04-25 | 2002-11-08 | Nitto Shinko Kk | マスキング材の製造方法及びマスキング材 |
JP2009197180A (ja) * | 2008-02-25 | 2009-09-03 | Toray Ind Inc | 耐光性エポキシ樹脂組成物およびそれを用いた繊維強化複合材料 |
JP2012077159A (ja) * | 2010-09-30 | 2012-04-19 | Fujifilm Corp | インク組成物、印画物及びその製造方法 |
JP2013133339A (ja) * | 2011-12-22 | 2013-07-08 | Nippon Zeon Co Ltd | エポキシ樹脂組成物、硬化物、透明封止材料及び光半導体装置 |
WO2015107903A1 (ja) * | 2014-01-17 | 2015-07-23 | 東レ株式会社 | 被覆繊維強化樹脂成形品およびその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20200148847A1 (en) | 2020-05-14 |
EP3653663A4 (en) | 2021-03-24 |
KR20200031064A (ko) | 2020-03-23 |
EP3653663A1 (en) | 2020-05-20 |
WO2019013025A1 (ja) | 2019-01-17 |
EP3653663B1 (en) | 2022-12-28 |
CN110650997A (zh) | 2020-01-03 |
AU2018300880A1 (en) | 2019-11-07 |
JP7215170B2 (ja) | 2023-01-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPWO2019013025A1 (ja) | 成形品およびその製造方法 | |
JP5604771B2 (ja) | エポキシ樹脂組成物、繊維強化複合材料およびその製造方法 | |
TWI439482B (zh) | 環氧聚合性組成物以及含該組成物的密封材組成物 | |
JP6007794B2 (ja) | 繊維強化複合材料用2液型エポキシ樹脂組成物および繊維強化複合材料 | |
EP3275924B1 (en) | Two-pack type epoxy resin composition for fiber-reinforced composite material, and fiber-reinforced composite material | |
KR20140018198A (ko) | 섬유 강화 복합 재료 rtm 성형용 에폭시 수지 조성물, 섬유 강화 복합 재료 및 그 제조 방법 | |
TW201247752A (en) | Prepreg and fiber reinforced composite material | |
EP3053941A1 (en) | Two-pack epoxy resin composition for fiber-reinforced composite material, and fiber-reinforced composite material | |
CN107955372A (zh) | 双马来酰亚胺树脂氰酸酯树脂复合材料的制备方法 | |
KR20190022488A (ko) | 섬유 강화 복합 재료용 2액형 에폭시 수지 조성물 및 섬유 강화 복합 재료 | |
JP2010163573A (ja) | エポキシ樹脂組成物およびそれを用いた繊維強化複合材料 | |
TWI729088B (zh) | 環氧樹脂組成物、碳纖維強化複合材及其製造方法 | |
RU2706661C1 (ru) | Эпоксидное связующее, препрег на его основе и изделие, выполненное из него | |
WO2022210246A1 (ja) | エポキシ樹脂組成物、エポキシ樹脂硬化物及びそれを用いた被覆繊維強化樹脂成形品 | |
BR112019021701A2 (pt) | Sistema de resina curável, processo para formar um material compósito de epóxi reforçado com fibra, e, material compósito reforçado com fibra | |
JP2014214169A (ja) | 繊維強化複合材料用2液型エポキシ樹脂組成物および繊維強化複合材料 | |
JP2012077124A (ja) | Rtm成形用エポキシ樹脂組成物および繊維強化複合材料 | |
JP2021138925A (ja) | 繊維強化複合材料中間体、繊維強化複合材料の製造方法 | |
JP2021175605A (ja) | 繊維強化複合材料中間体、繊維強化複合材料の製造方法 | |
TW201917165A (zh) | 高亮透明環氧樹脂組合物及應用 | |
WO2018029743A1 (ja) | 繊維強化複合材料用2液型エポキシ樹脂組成物および繊維強化複合材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210427 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220215 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220401 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220830 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20220930 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20221220 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20230102 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 7215170 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |