JP6804487B2 - 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 - Google Patents
熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 Download PDFInfo
- Publication number
- JP6804487B2 JP6804487B2 JP2018090400A JP2018090400A JP6804487B2 JP 6804487 B2 JP6804487 B2 JP 6804487B2 JP 2018090400 A JP2018090400 A JP 2018090400A JP 2018090400 A JP2018090400 A JP 2018090400A JP 6804487 B2 JP6804487 B2 JP 6804487B2
- Authority
- JP
- Japan
- Prior art keywords
- diol
- fiber
- thermoplastic polyurethane
- resin
- polyurethane resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229920005989 resin Polymers 0.000 title claims description 71
- 239000011347 resin Substances 0.000 title claims description 71
- 239000000203 mixture Substances 0.000 title claims description 55
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 43
- 239000000835 fiber Substances 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229920006306 polyurethane fiber Polymers 0.000 title 1
- 150000002009 diols Chemical class 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 229920005862 polyol Polymers 0.000 claims description 28
- 150000003077 polyols Chemical class 0.000 claims description 28
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- 229920001228 polyisocyanate Polymers 0.000 claims description 22
- 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 claims description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims description 18
- 239000012783 reinforcing fiber Substances 0.000 claims description 18
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 description 31
- 239000000047 product Substances 0.000 description 15
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- 239000011159 matrix material Substances 0.000 description 11
- 229920005749 polyurethane resin Polymers 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 229920005992 thermoplastic resin Polymers 0.000 description 10
- 238000000465 moulding Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000003733 fiber-reinforced composite Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 5
- 238000005452 bending Methods 0.000 description 5
- -1 carbonate diol Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011151 fibre-reinforced plastic Substances 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004917 carbon fiber Substances 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-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 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229920006231 aramid fiber Polymers 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000021189 garnishes Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003230 hygroscopic agent Substances 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- YPQKTLPPOXNDMC-UHFFFAOYSA-N isocyanic acid;methylcyclohexane Chemical compound N=C=O.CC1CCCCC1 YPQKTLPPOXNDMC-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011342 resin composition Substances 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
- 239000000126 substance Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4845—Polyethers containing oxyethylene units and other oxyalkylene units containing oxypropylene or higher oxyalkylene end groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- 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
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass 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
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/046—Reinforcing macromolecular compounds with loose or coherent fibrous material with synthetic macromolecular fibrous material
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
- C08K7/26—Silicon- containing compounds
-
- 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
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/04—Thermoplastic elastomer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
Description
本発明の実施の形態に係る熱可塑性ポリウレタン樹脂製造用2液硬化型組成物は、少なくとも、ジオール(A)を含むポリオール成分と、ジイソシアネート(B)を含むポリイソシアネート成分とから構成される。2液硬化型組成物とは、たとえば2種類の液を混合することにより硬化する、樹脂の原料である。
本発明の実施の形態に係る熱可塑性ポリウレタン樹脂製造用2液硬化型組成物におけるポリオール成分は、ジオール(A)を含む。
本発明の実施の形態に係るジオール(A)は、分子量が200〜700の芳香環を有するジオール(A−1)を含む。芳香環を有するジオール(A−1)としては、分子量が200〜700であること以外は特に限定されない。
本発明の実施の形態に係るジオール(A)は、分子量200〜700の芳香環を有するジオール(A−1)以外に、分子量500以下の芳香環を有しないジオール(A−2)を含む。芳香環を有しないジオール(A−2)として、たとえば、以下に説明する脂肪族ジオール、オキシアルキレン基を有するジオールおよび脂環式ジオール等を挙げることができる。芳香環を有しないジオール(A−2)は、これらの化合物を2種類以上含んでも良い。
本発明の実施の形態に係る熱可塑性ポリウレタン樹脂製造用2液硬化型組成物におけるイソシアネート成分は、ジイソシアネート(B)を含む。ジイソシアネート(B)としては、特に限定されないが、脂肪族ジイソシアネート、脂環式ジイソシアネート、芳香族ジイソシアネート(B−1)および芳香脂肪族ジイソシアネートが挙げられる。本発明の実施の形態に係るジイソシアネート(B)は、これらの化合物を2種類以上含んでも良い。
本発明の実施の形態に係るポリオール成分は、樹脂、具体的には硬化塗膜の引張物性を高める観点から、多孔質粉体(C)を含んでもよい。多孔質粉体(C)としては、無機の多孔質粉体が好ましく、ゼオライトがより好ましい。多孔質粉体(C)は、当該ポリオール成分100質量部に対して、1〜10質量部用いられることが好ましく、2〜8質量部用いられることがより好ましく、3〜7質量部用いられることがさらに好ましい。
本発明の実施の形態に係る熱可塑性ポリウレタン樹脂製造用2液硬化型組成物(以下、単に2液硬化型組成物とも称する。)は、上記ポリオール成分と上記ポリイソシアネート成分とを含むものであり、これらポリオール成分とポリイソシアネート成分との反応により熱可塑性樹脂が生成されるものである。すなわち、当該2液硬化型組成物は、反応生成物が熱可塑性樹脂になるという性質を持つものである。2液硬化型組成物は、ポリオール成分を第1液とし、ポリイソシアネート成分を第2液として、これら第1液と第2液を混ぜ合わせることにより両成分を反応硬化させることができる、2液硬化性の樹脂組成物である。
本発明の実施の形態に係る熱可塑性ポリウレタン樹脂は、上記ポリオール成分と上記イソシアネート成分との反応物を含む熱可塑性樹脂であり、一実施形態として上記2液硬化型組成物を反応させることにより得られる。
本発明の実施の形態に係る繊維強化樹脂は、上記した2液硬化型組成物の硬化物である熱可塑性ポリウレタン樹脂と、強化繊維と、を含むものである。具体的には、当該熱可塑性ポリウレタン樹脂は、繊維強化樹脂におけるマトリックス樹脂として用いられる。
本発明の実施の形態であると、混合時ならびに成形時の樹脂粘度が低いにもかかわらず、高いガラス転移温度を有する熱可塑性樹脂を提供することができる。成形時の樹脂粘度が低いことにより、強化繊維と複合化させる際のマトリックス樹脂の流動性を向上して、成形作業性を向上することができる。
・A−1−1:ビスフェノールAのプロピレンオキサイド付加体(分子量:360)
ADEKA社製「アデカポリエーテルBPX−11」
・A−1−2:ビスフェノールAのプロピレンオキサイド付加体(分子量:532)
三洋化成社製「ニューポールBP−5P」
・A−1−3:ビスフェノールAのエチレンオキサイド付加体(分子量:672)
三洋化成社製「ニューポールBPE−100」
・(比較用材料)A−1C:ビスフェノールAのプロピレンオキサイド付加体(分子量:790)
ADEKA社製「アデカポリエーテルBPX−55」
・A−2−1:1,4−ブタンジオール(分子量:90)
三菱ケミカル社製 「1,4−ブタンジオール」
・A−2−2:ジプロピレングリコール(分子量:134)
旭硝子社製「ジプロピレングリコール」
・A−2−3:2−エチル−1,3−ヘキサンジオール(分子量:146)
KHネオケム社製「2−エチル−1,3−ヘキサンジオール」
・A−2−4:トリプロピレングリコール(分子量:192)
旭硝子社製「トリプロピレングリコール」
・A−2−5:ポリプロピレングリコール(分子量400)
旭硝子社製「エクセノール420」
・(比較用材料)A−2C:ポリプロピレングリコール(分子量1000)
旭硝子社製「エクセノール1020」
・B−1−1:MDI(4,4’−MDIと2,4’−MDIとの混合物(50%:50%))
BASF INOAC ポリウレタン社製「ルプラネートMI」
・B−1−2:MDI(4,4’−MDI)
東ソー社製「ミリオネートMT」
・B−1−3:カルボジイミド変性MDI(4,4’−MDIのカルボジイミド変性体と4,4’−MDIとの混合物(25%:75%))
BASF INOAC ポリウレタン社製「ルプラネートMM−103」
・C−1:ゼオライト
ユニオン昭和社製「モレキュラーシーブ3AB」
・D−1:ジオクチルチンジラウレート(金属触媒)
日東化成(株)製「ネオスタンU810」
実施例1〜21および比較例1〜4の2液硬化型組成物について、以下の評価方法により、混合粘度、ガラス転移温度(Tg)、引張強さ、熱溶融温度、繊維強化樹脂の曲げ強度、および繊維強化樹脂の衝撃強さを評価した。結果を表1および表2に示す。
それぞれの上記混合物を25℃環境下に静置し、混合開始から5分後の粘度を測定した。粘度は、JIS K7117−1に準じ、BM型粘度計(東機産業(株)製)を用いて測定した。
それぞれの上記混合物を、混合後5分経過時に膜厚1mmとなるように塗布した。これを、120℃で1時間処理することにより、ポリウレタン樹脂のシートを得た。得られた樹脂シートから5mm×2cmの試験片を切り出し、JIS K7244−4に準じ、ユービーエム社製のRheogel E−4000にてガラス転移温度を測定した。
ガラス転移温度と同様の方法により、膜厚1mmのポリウレタン樹脂のシートを得た。得られたシートから、5mm×4cmの試験片を切り出し、JIS A6021−2011に準じ、インストロンジャパン社製のデジタル万能試験機(Instron 5581
)にて引張強さ(MPa)を測定した。
ガラス転移温度と同様の方法により、膜厚1mmのポリウレタン樹脂のシートを得た。得られたシートから、1mm×1mmの試験片を切り出し、JIS K7210に準じ、島津製作所社製の流動性試験機(島津フローテスタCFT−500D)にて1/2法温度を測定した。
平織の炭素繊維を製品型の上で重ね合わせ、それを離形フィルムで覆って密閉し真空パックした後、樹脂を流し込み、120℃で1時間硬化し膜厚2mmの繊維強化樹脂成型体を得た。得られた成型体から100mm×15mm×2mmの試験片を切り出し、JIS K7074に準じ、精密万能試験機(島津オートグラフAG−Xplus)を用いて3点曲げ強度を測定した。
曲げ強度と同様の方法により、膜厚2mmの繊維強化樹脂成型体を得た。得られた成型体から80mm×10mm×2mmの試験片を切り出し、JIS K7077に準じ、電動振子式試験機(インストロンMPXシリーズ電動振子式試験機)にてシャルピー衝撃強度を測定した。
Claims (7)
- ジオール(A)を含むポリオール成分と、ジイソシアネート(B)を含むポリイソシアネート成分と、を有する2液硬化型組成物であって、
前記ジオール(A)は、分子量が200〜700の芳香環を有するジオール(A−1)と、分子量が500以下の芳香環を有しないジオール(A−2)とを含み、
前記ジオール(A−1)と前記ジオール(A−2)との合計に対する前記ジオール(A−1)の質量比((A−1)/((A−1)+(A−2)))が(10/100)〜(75/100)である、繊維強化樹脂製造用熱可塑性ポリウレタン樹脂製造用2液硬化型組成物。 - 前記芳香環を有しないジオール(A−2)は、脂肪族ジオール、およびオキシアルキレン基を有するジオールの少なくともいずれか一方である、請求項1に記載の繊維強化樹脂製造用熱可塑性ポリウレタン樹脂製造用2液硬化型組成物。
- 前記ジイソシアネート(B)は、芳香族ジイソシアネート(B−1)を含む、請求項1または2に記載の繊維強化樹脂製造用熱可塑性ポリウレタン樹脂製造用2液硬化型組成物。
- 前記芳香環を有するジオール(A−1)は、ビスフェノールAのアルキレンオキサイド付加物である、請求項1〜3のいずれかに記載の繊維強化樹脂製造用熱可塑性ポリウレタン樹脂製造用2液硬化型組成物。
- 前記ポリオール成分は、さらに多孔質粉体(C)を含む、請求項1〜4のいずれか1項に記載の繊維強化樹脂製造用熱可塑性ポリウレタン樹脂製造用2液硬化型組成物。
- 請求項1〜5のいずれか1項に記載の繊維強化樹脂製造用熱可塑性ポリウレタン樹脂製造用2液硬化型組成物の反応物を含む、繊維強化樹脂製造用熱可塑性ポリウレタン樹脂。
- 請求項6に記載の繊維強化樹脂製造用熱可塑性ポリウレタン樹脂と、強化繊維とを含む、繊維強化樹脂。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018090400A JP6804487B2 (ja) | 2018-05-09 | 2018-05-09 | 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 |
CN201980028487.5A CN112088179B (zh) | 2018-05-09 | 2019-04-09 | 热塑性聚氨酯树脂制造用双液固化型组合物、热塑性聚氨酯树脂以及纤维强化树脂 |
PCT/JP2019/015425 WO2019216088A1 (ja) | 2018-05-09 | 2019-04-09 | 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 |
US17/053,476 US11891511B2 (en) | 2018-05-09 | 2019-04-09 | Two-component curable composition for manufacturing thermoplastic polyurethane resin, thermoplastic polyurethane resin, and fiber-reinforced resin |
EP19800530.8A EP3792293A4 (en) | 2018-05-09 | 2019-04-09 | TWO-COMPONENT CURING COMPOSITION FOR THE PRODUCTION OF THERMOPLASTIC POLYURETHANE RESIN, THERMOPLASTIC POLYURETHANE RESIN AND FIBER REINFORCED RESIN |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018090400A JP6804487B2 (ja) | 2018-05-09 | 2018-05-09 | 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019196432A JP2019196432A (ja) | 2019-11-14 |
JP6804487B2 true JP6804487B2 (ja) | 2020-12-23 |
Family
ID=68467922
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018090400A Active JP6804487B2 (ja) | 2018-05-09 | 2018-05-09 | 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11891511B2 (ja) |
EP (1) | EP3792293A4 (ja) |
JP (1) | JP6804487B2 (ja) |
CN (1) | CN112088179B (ja) |
WO (1) | WO2019216088A1 (ja) |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3845019A (en) * | 1972-01-28 | 1974-10-29 | Baychem Corp | Improved polyurethane elastomers |
JPS5792015A (en) | 1980-11-28 | 1982-06-08 | Sanyo Chem Ind Ltd | Rigid floor finishing composition |
DE3233384A1 (de) * | 1982-09-08 | 1984-03-08 | Akzo Gmbh, 5600 Wuppertal | Thermoplastische polyurethan-elastomere aus cyclohexan-1.4-diisocyanat |
JPS63205312A (ja) | 1987-02-20 | 1988-08-24 | Mitsubishi Gas Chem Co Inc | 不飽和ポリエステル樹脂組成物 |
DE3717060A1 (de) | 1987-05-21 | 1988-12-01 | Bayer Ag | Polyether-polycarbonat-diole, ihre herstellung und verwendung als ausgangsprodukte fuer polyurethankunststoffe |
KR900018194A (ko) * | 1988-10-28 | 1990-12-20 | 가또 미끼오 | 자기성 피복처리 제제 및 자기 기록 매체 |
US5491210A (en) * | 1989-04-21 | 1996-02-13 | Kimberly-Clark Corporation | Thermally reversible polymers |
US5100922A (en) * | 1989-06-13 | 1992-03-31 | Asahi Glass Company Ltd. | Method for producing a molded product of integral-skin polyurethane foam |
US5185420A (en) * | 1990-11-02 | 1993-02-09 | Olin Corporation | Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts |
KR20000069881A (ko) * | 1997-01-06 | 2000-11-25 | 오노 알버어스 | 열가소성 폴리우레탄을 포함하는 압력 민감 접착제 |
JPH10265544A (ja) | 1997-03-26 | 1998-10-06 | Nippon Polyurethane Ind Co Ltd | ポリイソシアヌレートフォーム用組成物、及びポリイソシアヌレートフォームの製造方法 |
JPH10330451A (ja) | 1997-05-30 | 1998-12-15 | Toyo Tire & Rubber Co Ltd | 高減衰性ポリウレタン化合物 |
JP3933281B2 (ja) * | 1997-12-03 | 2007-06-20 | 伊藤製油株式会社 | ウレタン系塗料組成物 |
JPH11186155A (ja) | 1997-12-18 | 1999-07-09 | Nikon Corp | 露光動作の評価方法、該方法を使用する走査型露光装置及び該装置を用いたデバイス製造方法 |
JP2003287924A (ja) | 2002-03-28 | 2003-10-10 | Seiko Epson Corp | トナー |
WO2005070997A1 (ja) | 2004-01-22 | 2005-08-04 | Ube Industries, Ltd. | 液状ポリエーテルカーボネートジオール化合物及びそれから得られる熱可塑性ポリウレタン |
JP2005232447A (ja) | 2004-01-22 | 2005-09-02 | Ube Ind Ltd | 液状ポリエーテルカーボネートジオール及び該ジオールをジオール成分に持つ熱可塑性ポリウレタン |
JP2011213867A (ja) * | 2010-03-31 | 2011-10-27 | Mitsui Chemicals Inc | 熱可塑性ポリウレタン樹脂、成形品、および、熱可塑性ポリウレタン樹脂の製造方法 |
US9051499B2 (en) * | 2010-12-08 | 2015-06-09 | Dow Global Technologie Llc | Two-part polyurethane adhesive for bonding fiber-reinforced plastics |
US9085464B2 (en) | 2012-03-07 | 2015-07-21 | Applied Nanostructured Solutions, Llc | Resistance measurement system and method of using the same |
JP6102065B2 (ja) | 2012-03-12 | 2017-03-29 | 富士ゼロックス株式会社 | 静電荷像現像用トナー、静電荷像現像剤、トナーカートリッジ、プロセスカートリッジ、画像形成装置及び画像形成方法 |
EP2700666A1 (de) * | 2012-08-24 | 2014-02-26 | Sika Technology AG | Struktureller Polyurethanklebstoff |
US10611872B2 (en) * | 2013-11-04 | 2020-04-07 | Basf Se | Methods for producing transparent, thermoplastic polyurethane having high mechanical strength and hardness |
WO2015144435A1 (de) * | 2014-03-27 | 2015-10-01 | Basf Se | Thermoplastisches formgedächtnismaterial |
ES2666842T3 (es) * | 2014-04-28 | 2018-05-08 | Covestro Deutschland Ag | Componentes compuestos de fibras y su producción |
US10563004B2 (en) * | 2015-03-27 | 2020-02-18 | Basf Se | Memory foam based on thermoplastic polyurethane |
US20180208708A1 (en) * | 2015-07-17 | 2018-07-26 | Mitsui Chemicals, Inc. | Rigid polyurethane resin composition, rigid polyurethane resin, molded article, and fiber reinforced plastic |
JP6866586B2 (ja) * | 2016-08-02 | 2021-04-28 | 横浜ゴム株式会社 | 2液硬化型ウレタン接着剤組成物 |
EP3333209B1 (en) * | 2016-12-07 | 2023-09-20 | Henkel AG & Co. KGaA | Thermoplastic polyurethane matrix resin |
JP6902918B2 (ja) | 2017-04-28 | 2021-07-14 | 第一工業製薬株式会社 | ポリウレタン樹脂用ポリオール組成物、ポリウレタン樹脂形成性組成物、複合材料 |
CN107501510A (zh) * | 2017-09-08 | 2017-12-22 | 肇庆高新区恒泰信息服务有限公司 | 一种低硬度聚氨酯弹性体材料 |
-
2018
- 2018-05-09 JP JP2018090400A patent/JP6804487B2/ja active Active
-
2019
- 2019-04-09 EP EP19800530.8A patent/EP3792293A4/en active Pending
- 2019-04-09 CN CN201980028487.5A patent/CN112088179B/zh active Active
- 2019-04-09 US US17/053,476 patent/US11891511B2/en active Active
- 2019-04-09 WO PCT/JP2019/015425 patent/WO2019216088A1/ja unknown
Also Published As
Publication number | Publication date |
---|---|
WO2019216088A1 (ja) | 2019-11-14 |
EP3792293A4 (en) | 2022-01-26 |
CN112088179B (zh) | 2022-11-04 |
CN112088179A (zh) | 2020-12-15 |
EP3792293A1 (en) | 2021-03-17 |
US20210130611A1 (en) | 2021-05-06 |
US11891511B2 (en) | 2024-02-06 |
JP2019196432A (ja) | 2019-11-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11965057B2 (en) | Two-liquid curable composition for forming thermoplastic matrix resin, matrix resin for fiber-reinforced composite material, and fiber-reinforced composite material | |
KR102481812B1 (ko) | 폴리이소시아누레이트 기재 중합체 및 섬유 강화된 복합재 | |
JP2018532820A (ja) | エポキシ接着剤用のブロック化ポリウレタン強化剤 | |
JP7373109B2 (ja) | ポリオール組成物、ポリウレタン樹脂形成性組成物、複合材料 | |
JP5247368B2 (ja) | エポキシ樹脂の製造方法 | |
JP5252711B2 (ja) | エポキシ樹脂組成物 | |
US11396597B2 (en) | Epoxy resin composition and cured object obtained therefrom | |
JP2018188510A (ja) | ポリウレタン樹脂用ポリオール組成物、ポリウレタン樹脂形成性組成物、複合材料 | |
CN112955495A (zh) | 热固性成型材料、纤维增强复合材料、纤维增强塑料用热固性环氧树脂组合物、热固性成型材料的制造方法、纤维增强塑料 | |
JP6804487B2 (ja) | 熱可塑性ポリウレタン樹脂製造用2液硬化型組成物、熱可塑性ポリウレタン樹脂および繊維強化樹脂 | |
JP6904454B1 (ja) | 2液硬化型接着剤組成物 | |
EP3604374B1 (en) | Polyol composition for polyurethane resin, polyurethane resin-forming composition, and composite material | |
CA1261530A (en) | Polyurethane compositions containing a polyhydroxyalkylphosphine oxide | |
JP6904455B1 (ja) | 2液硬化型接着剤組成物 | |
JP2011184616A (ja) | エポキシ樹脂組成物 | |
CN117659930B (zh) | 一种双组分聚氨酯结构胶及其制备方法和应用 | |
WO2023219007A1 (ja) | 熱硬化性樹脂組成物、成形品、繊維強化複合材料用成形材料および繊維強化複合材料 | |
JP2023065896A (ja) | シートモールディングコンパウンドおよび繊維強化複合材料 | |
CN116615480A (zh) | 热固性环氧树脂组合物及其成型品、纤维增强复合材料、纤维增强复合材料用成型材料、以及纤维增强复合材料的制造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200702 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20200702 |
|
A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20200731 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200804 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200911 |
|
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: 20201201 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20201202 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6804487 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |