TWI267524B - High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content - Google Patents
High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content Download PDFInfo
- Publication number
- TWI267524B TWI267524B TW091101965A TW91101965A TWI267524B TW I267524 B TWI267524 B TW I267524B TW 091101965 A TW091101965 A TW 091101965A TW 91101965 A TW91101965 A TW 91101965A TW I267524 B TWI267524 B TW I267524B
- Authority
- TW
- Taiwan
- Prior art keywords
- thermoplastic polyurethane
- polyurethane
- polyol
- secondary hydroxyl
- polyol component
- Prior art date
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- 229920005862 polyol Polymers 0.000 title claims abstract description 97
- 150000003077 polyols Chemical class 0.000 title claims abstract description 95
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 83
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims abstract description 67
- 239000004433 Thermoplastic polyurethane Substances 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000004970 Chain extender Substances 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 229920002635 polyurethane Polymers 0.000 claims abstract description 28
- 239000004814 polyurethane Substances 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 229920000570 polyether Polymers 0.000 claims description 41
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 40
- 239000005056 polyisocyanate Substances 0.000 claims description 25
- 229920001228 polyisocyanate Polymers 0.000 claims description 25
- 150000002009 diols Chemical class 0.000 claims description 21
- 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 claims description 20
- -1 hydroxyl group polyol Chemical group 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 230000005540 biological transmission Effects 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 229920006264 polyurethane film Polymers 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 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 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 2
- 229910052797 bismuth Inorganic materials 0.000 claims 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 2
- 229910052707 ruthenium Inorganic materials 0.000 claims 2
- DWGIDUHBATXDPW-UHFFFAOYSA-N CO.CO.CCCCCC.C1CCCCC1 Chemical compound CO.CO.CCCCCC.C1CCCCC1 DWGIDUHBATXDPW-UHFFFAOYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 229960004217 benzyl alcohol Drugs 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 239000000306 component Substances 0.000 claims 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims 1
- CVMNKHMWNZSNLW-UHFFFAOYSA-N hexane-1,6-diol;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.OCCCCCCO CVMNKHMWNZSNLW-UHFFFAOYSA-N 0.000 claims 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 claims 1
- 229910052747 lanthanoid Inorganic materials 0.000 claims 1
- 150000002602 lanthanoids Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 150000003303 ruthenium Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 3
- 125000005442 diisocyanate group Chemical group 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 12
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical class [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 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 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- DWANEFRJKWXRSG-UHFFFAOYSA-N 1,2-tetradecanediol Chemical compound CCCCCCCCCCCCC(O)CO DWANEFRJKWXRSG-UHFFFAOYSA-N 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 2
- 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 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- PHNGKIFUTBFGAG-UHFFFAOYSA-N 2-ethoxybenzene-1,4-diol Chemical compound CCOC1=CC(O)=CC=C1O PHNGKIFUTBFGAG-UHFFFAOYSA-N 0.000 description 1
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102100022260 Killin Human genes 0.000 description 1
- 101710193777 Killin Proteins 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
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- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- 239000010974 bronze Substances 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- VCVOSERVUCJNPR-UHFFFAOYSA-N cyclopentane-1,2-diol Chemical compound OC1CCCC1O VCVOSERVUCJNPR-UHFFFAOYSA-N 0.000 description 1
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- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
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- 239000005001 laminate film Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
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- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
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- 235000018553 tannin Nutrition 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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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
- C08G18/28—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
-
- 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
- C08G18/0895—Manufacture of polymers by continuous processes
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
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)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/781,791 US6734273B2 (en) | 2001-02-12 | 2001-02-12 | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI267524B true TWI267524B (en) | 2006-12-01 |
Family
ID=25123951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091101965A TWI267524B (en) | 2001-02-12 | 2002-02-05 | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6734273B2 (https=) |
| EP (1) | EP1366100B1 (https=) |
| JP (1) | JP2004522840A (https=) |
| KR (1) | KR20030076673A (https=) |
| CN (1) | CN100381478C (https=) |
| AT (1) | ATE389682T1 (https=) |
| AU (1) | AU2002242013A1 (https=) |
| BR (1) | BR0207167A (https=) |
| DE (1) | DE60225674T2 (https=) |
| ES (1) | ES2302514T3 (https=) |
| TW (1) | TWI267524B (https=) |
| WO (1) | WO2002064656A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI465472B (https=) * | 2012-11-19 | 2014-12-21 | ||
| TWI584932B (zh) * | 2012-11-19 | 2017-06-01 | Perfection Mighty Industrial Co Ltd | Instantaneous heating and mixing reaction device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7906199B2 (en) * | 2004-12-23 | 2011-03-15 | Ppg Industries Ohio, Inc. | Color harmonization coatings for articles of manufacture comprising different substrate materials |
| US20070020463A1 (en) * | 2004-12-23 | 2007-01-25 | Trainham James A | Flexible polymer coating and coated flexible substrates |
| US8389113B2 (en) * | 2002-09-17 | 2013-03-05 | Ppg Industries Ohio, Inc. | Substrates and articles of manufacture coated with a waterborne 2K coating composition |
| US20070004892A1 (en) * | 2005-07-01 | 2007-01-04 | Rye Karen R | Flexible polymer coating and coated flexible substrates |
| US7202322B2 (en) † | 2002-11-08 | 2007-04-10 | Noveon, Inc. | Heat resistant high moisture vapor transmission thermoplastic polyurethane |
| AU2004281178A1 (en) * | 2003-10-15 | 2005-04-28 | Tyco Healthcare Group, Lp | Method of joining materials |
| US7592398B1 (en) | 2004-06-18 | 2009-09-22 | Ppg Industries Ohio, Inc. | Flexible polymer coating and coated flexible substrates |
| WO2006047130A1 (en) * | 2004-10-25 | 2006-05-04 | Omnova Solutions Inc. | Moisture transmissive laminate |
| US20060141264A1 (en) * | 2004-12-23 | 2006-06-29 | Rearick Brian K | Soft feel coating for a rigid substrate |
| US7758949B1 (en) | 2005-02-08 | 2010-07-20 | Sloan Donald D | Thermal reactive ink transfer system |
| US20060258831A1 (en) * | 2005-05-10 | 2006-11-16 | Nigel Barksby | High molecular weight thermoplastic polyurethanes made from polyols having high secondary hydroxyl content |
| CN103788324A (zh) * | 2005-09-30 | 2014-05-14 | 路博润高级材料公司 | 含聚酯和聚醚二醇结构单元的热塑性聚氨酯 |
| WO2007048145A2 (en) * | 2005-10-21 | 2007-04-26 | Entrotech, Inc. | Protective sheets, articles, and methods |
| US8545960B2 (en) * | 2006-10-23 | 2013-10-01 | Entrotech, Inc. | Articles comprising protective sheets and related methods |
| EP2040066B1 (de) * | 2007-09-20 | 2017-03-08 | Oesch Sensor Technology Ag | Verwendung eines Sensormaterials für eine potentiometrische Elektrode |
| EP2193024A4 (en) | 2007-09-25 | 2013-11-06 | Entrotech Inc | PAINT SHEET FILMS, COMPOUNDS THEREOF AND RELATED METHODS |
| US10981371B2 (en) * | 2008-01-19 | 2021-04-20 | Entrotech, Inc. | Protected graphics and related methods |
| US20090246393A1 (en) * | 2008-03-27 | 2009-10-01 | Ppg Industries Ohio, Inc. | Polycarbodiimides |
| US20110054056A1 (en) * | 2008-05-22 | 2011-03-03 | Hefner Jr Robert E | Thermoset polyurethanes |
| US20100096062A1 (en) * | 2008-09-16 | 2010-04-22 | Serigraph, Inc. | Supported Article for Use in Decorating a Substrate |
| US20110033515A1 (en) * | 2009-08-04 | 2011-02-10 | Rst Implanted Cell Technology | Tissue contacting material |
| CN102770473B (zh) | 2010-02-26 | 2015-02-18 | 巴斯夫欧洲公司 | 热塑性聚氨酯的催化颗粒热处理 |
| US8455608B2 (en) | 2010-02-26 | 2013-06-04 | Basf Se | Catalyzed pellet heat treatment for thermoplastic polyurethanes |
| US8598248B2 (en) * | 2010-07-16 | 2013-12-03 | Bayer Materialscience Llc | Flexible polyurethane foams made from alkoxylated natural oil |
| WO2012078322A1 (en) * | 2010-12-07 | 2012-06-14 | Dow Global Technologies Llc | Polyurethane elastomers made using mixtures of aliphatic diol chain extender and secondary amine |
| US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
| WO2013138161A1 (en) * | 2012-03-12 | 2013-09-19 | Novomer, Inc. | Polymer compositions and methods |
| US20130255103A1 (en) | 2012-04-03 | 2013-10-03 | Nike, Inc. | Apparel And Other Products Incorporating A Thermoplastic Polymer Material |
| WO2018057379A1 (en) | 2016-09-20 | 2018-03-29 | Aero Advanced Paint Technology, Inc. | Paint film appliques with reduced defects, articles, and methods |
| CN110573548B (zh) * | 2017-04-26 | 2022-10-18 | 巴斯夫欧洲公司 | 使用包含多环芳族部分的聚酯多元醇制备聚氨酯的方法 |
| US12168712B2 (en) | 2018-11-29 | 2024-12-17 | Basf Se | Continuous production of a PPG-based TPU |
| WO2021026030A1 (en) | 2019-08-02 | 2021-02-11 | Nike, Inc. | An upper for an article of footwear |
| WO2021101979A1 (en) | 2019-11-18 | 2021-05-27 | Nike Innovate C.V. | Knitted component having a foam surface feature |
| BR112022016996A2 (pt) | 2020-02-28 | 2022-10-25 | Basf Se | Pelotas espumadas, processo de produção de pelotas espumadas, uso de pelotas espumadas e material híbrido |
| US12508487B2 (en) | 2020-11-20 | 2025-12-30 | Acushnet Company | Golf ball having at least one radar detectable mark |
| JP2025022805A (ja) | 2023-08-03 | 2025-02-14 | アクシュネット カンパニー | 少なくとも１つのレーダー検出可能マークを具備するゴルフボール |
| WO2025093626A1 (en) | 2023-10-31 | 2025-05-08 | Basf Se | Process for producing thermoplastic polyurethanes |
| EP4653063A1 (en) | 2024-05-24 | 2025-11-26 | Acushnet Company | Golf ball |
| EP4653064A1 (en) | 2024-05-24 | 2025-11-26 | Acushnet Company | Golf ball |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3829505A (en) | 1970-02-24 | 1974-08-13 | Gen Tire & Rubber Co | Polyethers and method for making the same |
| US4202957A (en) | 1974-09-09 | 1980-05-13 | The Upjohn Company | Thermoplastic polyurethane elastomers from polyoxypropylene polyoxyethylene block copolymers |
| US4131731A (en) | 1976-11-08 | 1978-12-26 | Beatrice Foods Company | Process for preparing polycarbonates |
| US4124572A (en) | 1977-07-05 | 1978-11-07 | Uniroyal, Inc. | Thermoplastic polyurethane elastomer |
| US4239879A (en) | 1979-06-25 | 1980-12-16 | The General Tire & Rubber Company | Thermoplastic polyurethane prepared from a poly-1,2-propylene ether glycol, a low molecular weight glycol and 2,4-tolylene diisocyanate |
| JPS61200114A (ja) * | 1985-02-28 | 1986-09-04 | Nippon Zeon Co Ltd | 抗血栓性ポリウレタン化合物及びその製造方法 |
| 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 |
| DE4125454A1 (de) * | 1991-08-01 | 1993-02-04 | Bayer Ag | Beschichtungsmittel und ihre verwendung zur erzeugung wasserdampfdurchlaessiger beschichtungen |
| US5677413A (en) | 1995-06-15 | 1997-10-14 | Arco Chemical Technology, L.P. | Polyurethane elastomers exhibiting improved demold green strength and water absorption and haze-free polyols suitable for their preparation |
| ATE198756T1 (de) | 1995-12-08 | 2001-02-15 | Huntsman Ici Chem Llc | Polyurethanelastomere |
| US5696221A (en) * | 1996-07-15 | 1997-12-09 | Arco Chemical Technology, L.P. | Polyurethane/urea heat-cured and moisture-cured elastomers with improved physical properties |
| KR100528640B1 (ko) * | 1996-10-11 | 2005-11-16 | 아르코 케미컬 테크날러쥐. 엘.피. | 개선된 스판덱스 엘라스토머 |
| EP0881244A3 (de) | 1997-05-27 | 2000-01-19 | Basf Aktiengesellschaft | Verfahren zur Herstellung von thermoplastischen Polyurethanen |
-
2001
- 2001-02-12 US US09/781,791 patent/US6734273B2/en not_active Expired - Lifetime
-
2002
- 2002-01-30 AT AT02707615T patent/ATE389682T1/de not_active IP Right Cessation
- 2002-01-30 ES ES02707615T patent/ES2302514T3/es not_active Expired - Lifetime
- 2002-01-30 AU AU2002242013A patent/AU2002242013A1/en not_active Abandoned
- 2002-01-30 WO PCT/US2002/002584 patent/WO2002064656A2/en not_active Ceased
- 2002-01-30 EP EP02707615A patent/EP1366100B1/en not_active Expired - Lifetime
- 2002-01-30 JP JP2002564983A patent/JP2004522840A/ja active Pending
- 2002-01-30 DE DE60225674T patent/DE60225674T2/de not_active Expired - Lifetime
- 2002-01-30 CN CNB028054989A patent/CN100381478C/zh not_active Expired - Fee Related
- 2002-01-30 KR KR20037010601A patent/KR20030076673A/ko not_active Abandoned
- 2002-01-30 BR BR0207167-3A patent/BR0207167A/pt active Search and Examination
- 2002-02-05 TW TW091101965A patent/TWI267524B/zh not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI465472B (https=) * | 2012-11-19 | 2014-12-21 | ||
| TWI584932B (zh) * | 2012-11-19 | 2017-06-01 | Perfection Mighty Industrial Co Ltd | Instantaneous heating and mixing reaction device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004522840A (ja) | 2004-07-29 |
| US20020156225A1 (en) | 2002-10-24 |
| KR20030076673A (ko) | 2003-09-26 |
| ES2302514T3 (es) | 2008-07-16 |
| BR0207167A (pt) | 2004-02-10 |
| DE60225674T2 (de) | 2009-04-02 |
| WO2002064656A3 (en) | 2002-10-24 |
| CN100381478C (zh) | 2008-04-16 |
| AU2002242013A1 (en) | 2002-08-28 |
| WO2002064656A2 (en) | 2002-08-22 |
| EP1366100B1 (en) | 2008-03-19 |
| CN1492892A (zh) | 2004-04-28 |
| ATE389682T1 (de) | 2008-04-15 |
| US6734273B2 (en) | 2004-05-11 |
| DE60225674D1 (de) | 2008-04-30 |
| EP1366100A2 (en) | 2003-12-03 |
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