JP2005509704A - 衝撃耐性ポリウレアウレタンおよび調製の方法 - Google Patents
衝撃耐性ポリウレアウレタンおよび調製の方法 Download PDFInfo
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- JP2005509704A JP2005509704A JP2003545705A JP2003545705A JP2005509704A JP 2005509704 A JP2005509704 A JP 2005509704A JP 2003545705 A JP2003545705 A JP 2003545705A JP 2003545705 A JP2003545705 A JP 2003545705A JP 2005509704 A JP2005509704 A JP 2005509704A
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- JP
- Japan
- Prior art keywords
- polyether
- polyureaurethane
- polyisocyanate
- prepolymer
- containing polyureaurethane
- 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.)
- Withdrawn
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- 229920000162 poly(ureaurethane) Polymers 0.000 title claims abstract description 108
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title description 5
- 229920000570 polyether Polymers 0.000 claims abstract description 146
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 145
- 239000000463 material Substances 0.000 claims abstract description 81
- 229920005862 polyol Polymers 0.000 claims abstract description 77
- 150000003077 polyols Chemical class 0.000 claims abstract description 77
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 54
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 54
- 150000001412 amines Chemical class 0.000 claims abstract description 38
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 238000000576 coating method Methods 0.000 claims abstract description 34
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- 238000009863 impact test Methods 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 66
- 239000000126 substance Substances 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical group CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 4
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical group CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical group CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 1
- 229920002396 Polyurea Polymers 0.000 claims 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 14
- 239000004814 polyurethane Substances 0.000 description 14
- 229920002635 polyurethane Polymers 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- 238000012360 testing method Methods 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000009102 absorption Effects 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000005266 casting Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- -1 polyoxypropylene Polymers 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 229920002176 Pluracol® Polymers 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical group 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- 239000006117 anti-reflective coating Substances 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000012963 UV stabilizer Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000001282 organosilanes Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 230000002028 premature Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001983 poloxamer Polymers 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 229920002359 Tetronic® Polymers 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003667 anti-reflective effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000008371 chromenes Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ZIZJPRKHEXCVLL-UHFFFAOYSA-N 1,3-bis(6-isocyanatohexyl)-1,3-diazetidine-2,4-dione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C1=O ZIZJPRKHEXCVLL-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- AFNINTOPXLZTNX-UHFFFAOYSA-N 2-[2-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCCCC1CCO AFNINTOPXLZTNX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PRIUALOJYOZZOJ-UHFFFAOYSA-L 2-ethylhexyl 2-[dibutyl-[2-(2-ethylhexoxy)-2-oxoethyl]sulfanylstannyl]sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS[Sn](CCCC)(CCCC)SCC(=O)OCC(CC)CCCC PRIUALOJYOZZOJ-UHFFFAOYSA-L 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- SPXWGAHNKXLXAP-UHFFFAOYSA-N 2-methylpentane-1,3-diol Chemical compound CCC(O)C(C)CO SPXWGAHNKXLXAP-UHFFFAOYSA-N 0.000 description 1
- VFUGUWZYXGNQHR-UHFFFAOYSA-N 2h-1,2-benzoxazine;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=C2C=CNOC2=C1 VFUGUWZYXGNQHR-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ITPCCQOGYMDBHK-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine;2,3-dihydro-1h-indole Chemical compound C1=CC=C2NCCC2=C1.C1=CC=CC2=C(C=CNO3)C3=CC=C21 ITPCCQOGYMDBHK-UHFFFAOYSA-N 0.000 description 1
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 1
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
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- 230000002939 deleterious effect Effects 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- SDTDHTCWRNVNAJ-UHFFFAOYSA-L dimethyltin(2+);diacetate Chemical compound CC(=O)O[Sn](C)(C)OC(C)=O SDTDHTCWRNVNAJ-UHFFFAOYSA-L 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
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- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
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- JNLPWEHDIDONKL-UHFFFAOYSA-L n'-anilino-n-phenyliminocarbamimidothioate;mercury(2+) Chemical compound [Hg+2].C=1C=CC=CC=1N=NC(/[S-])=N/NC1=CC=CC=C1.C=1C=CC=CC=1N=NC(/[S-])=N/NC1=CC=CC=C1 JNLPWEHDIDONKL-UHFFFAOYSA-L 0.000 description 1
- ITDHHRGCSPXWJP-UHFFFAOYSA-N n-chloro-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NCl ITDHHRGCSPXWJP-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
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- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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- 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
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- 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
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- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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- C08G18/40—High-molecular-weight compounds
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- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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Abstract
Description
a.ポリイソシアネートおよび少なくとも1つのポリエーテル含有ポリオール物質を含むポリウレアウレタンプレポリマー;ならびに
b.アミン含有硬化剤、
ここで、該プレポリマーは、2.0から4.5未満のNCO対OHの当量比を有する。
a.少なくとも1つのポリエーテル含有ポリオールとポリイソシアネートを反応させて、ポリエーテル含有ポリウレアウレタンプレポリマーを形成する工程;および
b.アミン含有硬化剤と該プレポリマーを反応させる、工程であって、ここで、該プレポリマーは、2.0から4.5未満のNCO対OHの当量比を有する。
%NCO=(mLブランク−mLサンプル)(HCl規定度)(4.2018)/サンプル重量、グラム;
IEW=(サンプル重量、グラム)1000/(mLブランク−mLサンプル)(HCl規定度)。
「HCl規定度」の値を、以下のように決定し得る。以前に計量されたビーカーに0.4gの第1標準Na2CO3を加え得、この重量を、記録し得る。これに50mLの脱イオン化水およびNa2CO3を加え得、磁気による撹拌で溶解し得る。Titrino751自動滴定機を使用して、1N HClを用いて第1標準液を滴定し得、この容積を記録し得る。この手順は、合計3回の滴定のためにさらに2回繰り返され得、この平均は、以下の式に従って規定度として使用され得る。
%NCO=(ブランクmL−サンプルmL)(HCl規定度)(4.2018)/サンプル重量、グラム
IEW=(サンプル重量、グラム)1000/(ブランクmL−サンプルmL)(HCl規定度)。
に従って、自動的に算出した。「HCl規定度」値を、以下のように決定した。前もって計量したビーカーに、0.4グラムのNa2CO3第一標準物質を加え、重量を記録した。これに、50mLの脱イオン水を加え、Na2CO3を磁気攪拌しながら溶解した。組み合せのpH電極(すなわち、Metrohm組み合せガラス電極、番号6.0222.100)を備える自動滴定装置(すなわち、50mLのビュレットを備えるMetrohm GPD Titrino 751動的自動滴定装置)を使用して、1N HClで第一標準物質を滴定し、その容量を記録した。この工程を、3回の滴定の全てに対して、さらに2回繰り返し、そして平均を、以下の式:
HCl規定度=標準物質重量、グラム/(HCl mL)(0.053)。
に従って、規定度として使用した。
窒素ブランケットを含む反応容器中で、4.5当量の400MWポリカプロラクトン、0.58当量の750MWポリカプロラクトン、3.387当量のトリメチロールプロパン、1.695当量のPluracol P2000および27.44当量のDesmodur Wを、室温で一緒に混合した。Desmodur Wは、20重量パーセントのトランス−トランス異性体ならびに80重量パーセントのシス−シス異性体およびシス−トランス異性体を含む、4,4’−メチレンビス(シクロヘキシルイソシアネート(isocyante))を表す。Desmodur Wは、Bayer Corporationから入手し、Pluracol P2000はBASFから入手した。反応混合物を78℃の温度まで加熱して、実質的に透明な混合物を得た。この混合物に、20ppmのジブチルスズラウリエート(dibutyltinlaureate)触媒を加え、熱を除去した。触媒の添加は発熱反応を生じ、温度が上昇し始め、123℃で最高となった。持続的にかき混ぜながら反応を行い、そして周囲条件下で冷却した。約116℃の温度で、以下の物質を加えた:0.5wt%のIrganox 1010(Ciba Geigyから入手)、2wt%のUV吸収装置Cyasorb 5411(American Cyanamid/Cytecから入手)および1.5ppmのExalite Blue 78−13(Excitonから入手)。混合物を、さらに1時間、100℃でかき混ぜ、次いで、室温まで冷却した。この混合物を成分Aプレポリマーという。成分Aプレポリマーのイソシアネート(NCO)濃度を、上記の工程に従って、決定した。理論的なNCO%を、10.3であると決定し、そして実験的なNCO%は10.1であった。次いで、成分Aプレポリマーを上記のレンズの注型工程中で使用し、そして結果として得られたレンズを上記の対象手順を使用して、高衝撃試験を行った。このレンズは、1秒あたり150フィートの最高速度に耐え得た。
Pluracol P2000の代わりに1.695のPluronic L62Dを使用したこと以外は、実施例2について、実施例1に記載したのと同じ手順を使用した。理論上のNCO%を10.3であると決定し、そして実験的なNCO%は10.1であった。次いで、成分Aプレポリマーを、上記のレンズの注型工程中で使用し、そして結果として得られたレンズを上記の対象手順を使用して、高衝撃試験を行った。このレンズは、1秒あたり300フィートの速度で、破損および/または破砕しなかった。
Pluracol P2000の代わりに1.356当量のPluracol P2000と0.338当量のPluracol E2000の混合物を使用したこと以外は、実施例3について、実施例1に記載したのと同じ手順を使用した。理論上のNCO%を10.3であると決定し、そして実験的なNCO%は9.02であった。次いで、成分Aプレポリマーを、上記のレンズの注型工程中で使用し、そして結果として得られたレンズを上記の対象手順を使用して、高衝撃試験を行った。このレンズは、1秒あたり137フィートの最高速度に耐え得た。
Pluracol P2000の代わりに1.695当量のToneTMPolyol 0241を使用したこと以外は、実施例4について、実施例1に記載したのと同じ手順を使用した。成分Aプレポリマーを、上記のレンズの注型工程中で使用し、そして結果として得られたレンズを上記の対象手順を使用して、高衝撃試験を行った。このレンズは、1秒あたり146フィートの最高速度に耐え得た。
Claims (62)
- ポリエーテル含有ポリウレアウレタンであって、該ポリウレアウレタンは、少なくとも部分的に硬化され、かつ両面に硬性コーティングを有する、平面構造の、2.2mmの最大中心厚さを有するレンズとして試験される場合、高衝撃試験によって規定される場合に、1秒間あたり少なくとも148フィートの衝撃耐性を有する、ポリエーテル含有ポリウレアウレタン。
- ポリエーテルポリオールから誘導されるブロック部分を含む、請求項1に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテルポリオールが、以下の式:
H−(O−CRRCRR−Yn)a−(CRRCRR−Yn−O)b−(CRRCRR−Yn−O)c−H
を有し、ここで、Rは、水素またはC1〜C6アルキルを表し得;Yは、CH2を表し得;nは、0〜6の整数であり得;a、b、およびcは、各々、0〜300の整数であり得、ここで、a、bおよびcは、該ポリオールの重量平均分子量が32,000を超えないように選択される、請求項2に記載のポリエーテル含有ポリウレアウレタン。 - 73℃において2,000cPs未満の粘度を有する、請求項1に記載のポリエーテル含有ポリウレアウレタン。
- プレポリマーおよびアミン含有硬化剤を含む、請求項1に記載のポリエーテル含有ポリウレアウレタン。
- 前記プレポリマーが、ポリイソシアネートおよび少なくとも1種のポリエーテル含有ポリオール材料を含む、請求項5に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、脂肪族ポリイソシアネート、脂環式ポリイソシアネート、芳香族ポリイソシアネート、およびこれらの混合物から選択される、請求項6に記載のポリエーテルポリウレアウレタン。
- 前記ポリイソシアネートが、脂肪族ジイソシアネート、脂環式ジイソシアネート、およびこれらの混合物から選択される、請求項7に記載のポリエーテルポリウレアウレタン。
- 前記ポリイソシアネートが、シクロヘキシルメタンおよびその異性体混合物から選択される、請求項7に記載のポリエーテルポリウレアウレタン。
- 前記ポリイソシアネートが、4,4’−メチレンビス(シクロヘキシルイソシアネート)のトランス−トランス異性体から選択される、請求項7に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、3−イソシアナト−メチル−3,5,5−トリメチルシクロヘキシル−イソシアネート;メタ−テトラメチルキシレンジイソシアネート(1,3−ビス(1−イソシアナト−1−メチルエチル)−ベンゼン)およびこれらの混合物から選択される、請求項7に記載のポリエーテル含有ポリウレアウレタン。
- 前記プレポリマーが、2.0〜4.5未満のNCO/OH当量比を有する、請求項5に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、ポリエーテルポリオールおよびその混合物から選択される、請求項5に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、200〜32,000の重量平均分子量を有する、請求項6に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、2,000〜15,000の数平均分子量を有する、請求項14に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、4,4’−メチレンビス(3−クロロ−2,6−ジエチルアニリン)である、請求項5に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、2,4−ジアミノ−3,5−ジエチル−トルエン;2,6−ジアミノ−3,5−ジエチル−トルエン、およびこれらの混合物から選択される、請求項5に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、1.0 NCO/0.60 NH2〜1.0 NCO/1.20 NH2のNCO/NH2当量比を有する、請求項5に記載のポリエーテル含有ポリウレアウレタン。
- ポリエーテル含有ポリウレアウレタンであって、以下:
(a)ポリイソシアネートおよび少なくとも1種のポリエーテル含有ポリオールを含む、プレポリマー;ならびに
(b)アミン含有硬化剤、
の反応生成物を含み、ここで、該プレポリマーが、2.0〜4.5未満のNCO/OH当量比を有する、ポリエーテル含有ポリウレアウレタン。 - 2.1〜4.0のNCO/OH当量比を有する、請求項20に記載のポリエーテル含有ポリウレアウレタン。
- ポリエーテルポリオールから誘導されるブロック部分を含む、請求項20に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテルポリオールが、以下の式:
H−(O−CRRCRR−Yn)a−(CRRCRR−Yn−O)b−(CRRCRR−Yn−O)c−H
を有し、ここで、Rは、水素またはC1〜C6アルキルを表し得;Yは、CH2を表し得;nは、0〜6の整数であり得;a、b、およびcは、各々、0〜300の整数であり得、ここで、a、bおよびcは、該ポリオールの重量平均分子量が32,000を超えないように選択される、請求項22に記載のポリエーテル含有ポリウレアウレタン。 - 73℃において2,000cPs未満の粘度を有する、請求項20に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリウレアウレタンが、プレポリマーおよびアミン含有硬化剤を含む、請求項20に記載のポリエーテル含有ポリウレアウレタン。
- 前記プレポリマーが、ポリイソシアネートおよび少なくとも1種のポリエーテル含有ポリオール材料を含む、請求項25に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、脂肪族ポリイソシアネート、脂環式ポリイソシアネート、芳香族ポリイソシアネート、およびこれらの混合物から選択される、請求項26に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、脂肪族ジイソシアネート、脂環式ジイソシアネート、およびこれらの混合物から選択される、請求項27に記載のポリエーテルポリウレアウレタン。
- 前記ポリイソシアネートが、シクロヘキシルメタンおよびその異性体混合物から選択される、請求項26に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、4,4’−メチレンビス(シクロヘキシルイソシアネート)のトランス,トランス異性体から選択される、請求項26に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、3−イソシアナト−メチル−3,5,5−トリメチルシクロヘキシル−イソシアネート;メタ−テトラメチルキシレンジイソシアネート(1,3−ビス(1−イソシアナト−1−メチルエチル)−ベンゼン)およびこれらの混合物から選択される、請求項26に記載のポリエーテル含有ポリウレアウレタン。
- 前記プレポリマーが、2.0〜4.5未満のNCO/OH当量比を有する、請求項25に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、ポリエーテルポリオールおよびその混合物から選択される、請求項26に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、200〜32,000の重量平均分子量を有する、請求項26に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、2,000〜15,000の数平均分子量を有する、請求項29に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、4,4’−メチレンビス(3−クロロ−2,6−ジエチルアニリン)である、請求項25に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、2,4−ジアミノ−3,5−ジエチル−トルエン;2,6−ジアミノ−3,5−ジエチル−トルエン、およびこれらの混合物から選択される、請求項25に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、1.0 NCO/0.60 NH2〜1.0 NCO/1.20 NH2のNCO/NH2当量比を有する、請求項25に記載のポリエーテル含有ポリウレアウレタン。
- ポリエーテル含有ポリウレアウレタンを調製する方法であって、以下の工程:
(a)ポリイソシアネートを、少なくとも1種のポリエーテル含有ポリオールと反応させて、ポリエーテル含有ポリウレアプレポリマーを形成する工程;および
(b)該プレポリマーを、アミン含有硬化剤と反応させる工程、
を包含し、ここで、該プレポリマーが、2.0〜4.5未満のNCO/OH当量比を有する、方法。 - 2,000cPs未満の粘度を有する、請求項40に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリウレアウレタンが、プレポリマーおよびアミン含有硬化剤を含む、請求項40に記載のポリエーテル含有ポリウレアウレタン。
- 前記プレポリマーが、ポリイソシアネートおよび少なくとも1種のポリエーテル含有ポリオール材料を含む、請求項42に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、脂肪族ポリイソシアネート、脂環式ポリイソシアネート、芳香族ポリイソシアネート、およびこれらの混合物から選択される、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、脂肪族ジイソシアネート、脂環式ジイソシアネート、およびこれらの混合物から選択される、請求項44に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、シクロヘキシルメタンおよびその異性体混合物から選択される、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、4,4’−メチレンビス(シクロヘキシルイソシアネート)のトランス−トランス異性体から選択される、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリイソシアネートが、3−イソシアナト−メチル−3,5,5−トリメチルシクロヘキシル−イソシアネート;メタ−テトラメチルキシレンジイソシアネート(1,3−ビス(1−イソシアナト−1−メチルエチル)−ベンゼン)およびこれらの混合物から選択される、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記プレポリマーが、2.1〜4.0未満のNCO/OH当量比を有する、請求項42に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、ポリエーテルポリオールおよびその混合物から選択される、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、200〜32,000の数平均分子量を有する、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテル含有ポリオール材料が、2,000〜15,000の数平均分子量を有する、請求項46に記載のポリエーテル含有ポリウレアウレタン。
- ポリエーテルポリオールから誘導されるブロック部分を含む、請求項43に記載のポリエーテル含有ポリウレアウレタン。
- 前記ポリエーテルポリオールが、以下の式:
H−(O−CRRCRR−Yn)a−(CRRCRR−Yn−O)b−(CRRCRR−Yn−O)c−H
を有し、ここで、Rは、水素またはC1〜C6アルキルを表し得;Yは、CH2を表し得;nは、0〜6の整数であり得;a、b、およびcは、各々、0〜300の整数であり得、ここで、a、bおよびcは、該ポリオールの重量平均分子量が32,000を超えないように選択される、請求項43に記載のポリエーテル含有ポリウレアウレタン。 - 前記アミン含有硬化剤が、4,4’−メチレンビス(3−クロロ−2,6−ジエチルアニリン)である、請求項42に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、2,4−ジアミノ−3,5−ジエチル−トルエン;2,6−ジアミノ−3,5−ジエチル−トルエン、およびこれらの混合物から選択される、請求項42に記載のポリエーテル含有ポリウレアウレタン。
- 前記アミン含有硬化剤が、1.0 NCO/0.60 NH2〜1.0 NCO/1.20 NH2のNCO/NH2当量比を有する、請求項42に記載のポリエーテル含有ポリウレアウレタン。
- ポリエーテル含有ポリウレアウレタンを含む光学物品であって、該ポリエーテル含有ポリウレアウレタンは、少なくとも部分的に硬化され、かつ両面に硬性コーティングを有する、平面構造の、2.2mmの最大中心厚さを有するレンズとして試験される場合、高衝撃試験によって規定される場合に、1秒間あたり少なくとも148フィートの衝撃耐性を有する、光学物品。
- ポリエーテル含有ポリウレアウレタンを含む光学物品であって、該ポリエーテル含有ポリウレアウレタンは、以下:
(a)ポリイソシアネートおよび少なくとも1種のポリエーテル含有ポリオールを含む、プレポリマー;ならびに
(b)アミン含有硬化剤、
の反応生成物を含み、ここで、該プレポリマーが、2.0〜4.5のNCO/OH当量比を有する、光学物品。 - ポリエーテル含有ポリウレアウレタンを含むフォトクロミック物品であって、該ポリエーテル含有ポリウレアウレタンは、少なくとも部分的に硬化され、かつ両面に硬性コーティングを有する、平面構造の、2.2mmの最大中心厚さを有するレンズとして試験される場合、高衝撃試験によって規定される場合に、1秒間あたり少なくとも148フィートの衝撃耐性を有する、フォトクロミック物品。
- ポリエーテル含有ポリウレアウレタンを含むフォトクロミック物品であって、該ポリエーテル含有ポリウレアウレタンは、以下:
(a)ポリイソシアネートおよび少なくとも1種のポリエーテル含有ポリオールを含む、プレポリマー;ならびに
(b)アミン含有硬化剤、
の反応生成物を含み、ここで、該プレポリマーが、2.0〜4.5のNCO/OH当量比を有する、フォトクロミック物品。
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US33282701P | 2001-11-16 | 2001-11-16 | |
US10/287,880 US20030096935A1 (en) | 2001-11-16 | 2002-11-05 | Impact resistant polyureaurethane and method of preparation |
PCT/US2002/036471 WO2003044071A1 (en) | 2001-11-16 | 2002-11-14 | Impact resistant polyureaurethane and method of preparation |
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EP (1) | EP1444281B1 (ja) |
JP (2) | JP2005509704A (ja) |
KR (1) | KR100638194B1 (ja) |
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CA (1) | CA2467193A1 (ja) |
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-
2002
- 2002-11-05 US US10/287,880 patent/US20030096935A1/en not_active Abandoned
- 2002-11-14 AU AU2002352686A patent/AU2002352686B2/en not_active Ceased
- 2002-11-14 DE DE60235712T patent/DE60235712D1/de not_active Expired - Lifetime
- 2002-11-14 TW TW091133409A patent/TW200300420A/zh unknown
- 2002-11-14 WO PCT/US2002/036471 patent/WO2003044071A1/en active Search and Examination
- 2002-11-14 EP EP02789634A patent/EP1444281B1/en not_active Revoked
- 2002-11-14 HU HU0500847A patent/HUP0500847A2/hu unknown
- 2002-11-14 BR BRPI0214235-0A patent/BR0214235A/pt not_active Application Discontinuation
- 2002-11-14 KR KR1020047007432A patent/KR100638194B1/ko active IP Right Grant
- 2002-11-14 CA CA002467193A patent/CA2467193A1/en not_active Abandoned
- 2002-11-14 MX MXPA04004651A patent/MXPA04004651A/es active IP Right Grant
- 2002-11-14 CN CNB028256476A patent/CN100516105C/zh not_active Expired - Fee Related
- 2002-11-14 AT AT02789634T patent/ATE461233T1/de not_active IP Right Cessation
- 2002-11-14 JP JP2003545705A patent/JP2005509704A/ja not_active Withdrawn
- 2002-11-14 ES ES02789634T patent/ES2339753T3/es not_active Expired - Lifetime
-
2004
- 2004-05-13 IL IL161981A patent/IL161981A/en active IP Right Grant
-
2005
- 2005-10-20 HK HK05109357.3A patent/HK1077312A1/xx not_active IP Right Cessation
-
2007
- 2007-03-01 JP JP2007051931A patent/JP2007146181A/ja active Pending
- 2007-03-14 US US11/685,794 patent/US20070155940A1/en not_active Abandoned
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JP2009536257A (ja) * | 2006-05-05 | 2009-10-08 | ピーピージー インダストリーズ オハイオ インコーポレーテツド | チオエーテル官能性ポリチオールオリゴマーおよびそれから調製される物品 |
JP2009536255A (ja) * | 2006-05-05 | 2009-10-08 | ピーピージー インダストリーズ オハイオ インコーポレーテツド | チオエーテル官能性ポリチオールオリゴマーから調製される組成物および物品 |
WO2012018070A1 (ja) * | 2010-08-06 | 2012-02-09 | 株式会社トクヤマ | フォトクロミック組成物 |
JP2012052091A (ja) * | 2010-08-06 | 2012-03-15 | Tokuyama Corp | フォトクロミック組成物 |
AU2011286681B2 (en) * | 2010-08-06 | 2014-01-16 | Tokuyama Corporation | Photochromic composition |
US9234984B2 (en) | 2010-08-06 | 2016-01-12 | Tokuyama Corporation | Photochromic composition |
WO2013099640A1 (ja) | 2011-12-26 | 2013-07-04 | 株式会社トクヤマ | フォトクロミック組成物 |
JPWO2013099640A1 (ja) * | 2011-12-26 | 2015-05-07 | 株式会社トクヤマ | フォトクロミック組成物 |
US9316765B2 (en) | 2011-12-26 | 2016-04-19 | Tokuyama Corporation | Photochromic composition |
JP7033605B2 (ja) | 2017-03-01 | 2022-03-10 | ヤンガー・マニュファクチャリング・カンパニー・ドゥーイング/ビジネス/アズ・ヤンガー・オプティックス | フォトクロミックアイウェアレンズの製造方法およびフォトクロミックアイウェア製品 |
Also Published As
Publication number | Publication date |
---|---|
HK1077312A1 (en) | 2006-02-10 |
CN100516105C (zh) | 2009-07-22 |
AU2002352686A1 (en) | 2003-06-10 |
KR100638194B1 (ko) | 2006-10-26 |
EP1444281A1 (en) | 2004-08-11 |
WO2003044071A1 (en) | 2003-05-30 |
KR20040094664A (ko) | 2004-11-10 |
BR0214235A (pt) | 2006-09-19 |
CA2467193A1 (en) | 2003-05-30 |
TW200300420A (en) | 2003-06-01 |
AU2002352686B2 (en) | 2006-06-22 |
MXPA04004651A (es) | 2004-08-12 |
DE60235712D1 (de) | 2010-04-29 |
EP1444281B1 (en) | 2010-03-17 |
IL161981A (en) | 2010-11-30 |
US20030096935A1 (en) | 2003-05-22 |
ATE461233T1 (de) | 2010-04-15 |
ES2339753T3 (es) | 2010-05-25 |
JP2007146181A (ja) | 2007-06-14 |
CN1633451A (zh) | 2005-06-29 |
HUP0500847A2 (en) | 2007-07-30 |
US20070155940A1 (en) | 2007-07-05 |
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