JP2003524684A - ビス置換オキセタンモノマーを基剤としたアモルファスポリエーテルグリコール - Google Patents
ビス置換オキセタンモノマーを基剤としたアモルファスポリエーテルグリコールInfo
- Publication number
- JP2003524684A JP2003524684A JP2001511522A JP2001511522A JP2003524684A JP 2003524684 A JP2003524684 A JP 2003524684A JP 2001511522 A JP2001511522 A JP 2001511522A JP 2001511522 A JP2001511522 A JP 2001511522A JP 2003524684 A JP2003524684 A JP 2003524684A
- Authority
- JP
- Japan
- Prior art keywords
- oxetane
- fox
- heptafluorobutoxymethyl
- monomer
- fluorinated
- 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.)
- Pending
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 203
- -1 bis-substituted oxetane Chemical class 0.000 title claims abstract description 53
- 229920000570 polyether Polymers 0.000 title claims description 49
- 239000004721 Polyphenylene oxide Substances 0.000 title claims description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title description 67
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 299
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 125
- 239000000203 mixture Substances 0.000 claims abstract description 103
- 229920000642 polymer Polymers 0.000 claims abstract description 97
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 72
- 229920003225 polyurethane elastomer Polymers 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 229920001971 elastomer Polymers 0.000 claims description 57
- 239000000806 elastomer Substances 0.000 claims description 55
- 239000000126 substance Substances 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 34
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- 239000004971 Cross linker Substances 0.000 claims description 28
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 150000002921 oxetanes Chemical class 0.000 claims description 23
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 22
- 229920001187 thermosetting polymer Polymers 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- KNLXBOKBOCQJTG-UHFFFAOYSA-N 3-methyl-3-(2,2,2-trifluoroethoxymethyl)oxetane Chemical compound FC(F)(F)COCC1(C)COC1 KNLXBOKBOCQJTG-UHFFFAOYSA-N 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
- 229920005862 polyol Polymers 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 8
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 8
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 8
- 239000004970 Chain extender Substances 0.000 claims description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- 229920000768 polyamine Polymers 0.000 claims description 5
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical compound CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- HEYQAPHUQYODBI-UHFFFAOYSA-N 3-(2,2,2-trifluoroethoxymethyl)oxetane Chemical compound FC(F)(F)COCC1COC1 HEYQAPHUQYODBI-UHFFFAOYSA-N 0.000 claims 12
- MVXDQPWDKQXWJF-UHFFFAOYSA-N 3-(2,2,3,3,4,4,4-heptafluorobutoxymethyl)-3-(2,2,2-trifluoroethoxymethyl)oxetane Chemical group FC(F)(F)C(F)(F)C(F)(F)COCC1(COCC(F)(F)F)COC1 MVXDQPWDKQXWJF-UHFFFAOYSA-N 0.000 claims 8
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 claims 4
- QZYAQRJJGPOBHO-UHFFFAOYSA-N 3-(2,2,3,3,4,4,4-heptafluorobutoxymethyl)-3-methyloxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)COCC1(C)COC1 QZYAQRJJGPOBHO-UHFFFAOYSA-N 0.000 claims 3
- SPCZTNDZQKQHDT-UHFFFAOYSA-N 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecoxymethyl)-3-methyloxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOCC1(C)COC1 SPCZTNDZQKQHDT-UHFFFAOYSA-N 0.000 claims 3
- XCBUJZSDVFFWHE-UHFFFAOYSA-N 3-methyl-3-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxymethyl)oxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)COCC1(C)COC1 XCBUJZSDVFFWHE-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 2
- FEOPWEMPQGJKCX-UHFFFAOYSA-N 3-(2,2,3,3,4,4,4-heptafluorobutoxymethyl)-3-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctoxymethyl)oxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)COCC1(COCC(F)(F)C(F)(F)C(F)(F)F)COC1 FEOPWEMPQGJKCX-UHFFFAOYSA-N 0.000 claims 1
- LQNTUZNRNFCSPU-UHFFFAOYSA-N 3-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecoxymethyl)-3-(2,2,2-trifluoroethoxymethyl)oxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOCC1(COCC(F)(F)F)COC1 LQNTUZNRNFCSPU-UHFFFAOYSA-N 0.000 claims 1
- BLEKNANGAFKAAG-UHFFFAOYSA-N 3-methyl-2-(2,2,2-trifluoroethoxymethyl)oxetane Chemical compound CC1COC1COCC(F)(F)F BLEKNANGAFKAAG-UHFFFAOYSA-N 0.000 claims 1
- FUKBVIWXOZPQGY-UHFFFAOYSA-N 3-methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctoxymethyl)oxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCOCC1(C)COC1 FUKBVIWXOZPQGY-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000463 material Substances 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 229920002635 polyurethane Polymers 0.000 description 45
- 239000004814 polyurethane Substances 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 43
- 239000003921 oil Substances 0.000 description 43
- 239000003054 catalyst Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 36
- 239000004809 Teflon Substances 0.000 description 31
- 229920006362 Teflon® Polymers 0.000 description 29
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 27
- 239000003999 initiator Substances 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 25
- 239000000758 substrate Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 229910052731 fluorine Inorganic materials 0.000 description 22
- 238000005227 gel permeation chromatography Methods 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 20
- 125000004122 cyclic group Chemical group 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 20
- 230000009477 glass transition Effects 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000005056 polyisocyanate Substances 0.000 description 17
- 229920001228 polyisocyanate Polymers 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 150000002334 glycols Chemical class 0.000 description 14
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 14
- 238000007334 copolymerization reaction Methods 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- QKFCXWZBHYFIHE-UHFFFAOYSA-N 3,3-bis(2,2,3,3,4,4,4-heptafluorobutoxymethyl)oxetane Chemical compound FC(F)(F)C(F)(F)C(F)(F)COCC1(COCC(F)(F)C(F)(F)C(F)(F)F)COC1 QKFCXWZBHYFIHE-UHFFFAOYSA-N 0.000 description 10
- 238000005299 abrasion Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 150000004292 cyclic ethers Chemical class 0.000 description 9
- 230000002209 hydrophobic effect Effects 0.000 description 9
- BMMZDTNPYHSDMO-UHFFFAOYSA-N oxolane-2-carboxylic acid;trifluoroborane Chemical group FB(F)F.OC(=O)C1CCCO1 BMMZDTNPYHSDMO-UHFFFAOYSA-N 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000012975 dibutyltin dilaurate Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229920005604 random copolymer Polymers 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- VMJRXKQPAMYKLG-UHFFFAOYSA-N 3,3-bis(2,2,2-trifluoroethoxymethyl)oxetane Chemical compound FC(F)(F)COCC1(COCC(F)(F)F)COC1 VMJRXKQPAMYKLG-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000005228 aryl sulfonate group Chemical group 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229920006311 Urethane elastomer Polymers 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 229920001973 fluoroelastomer Polymers 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ANRASKQFUDPONQ-UHFFFAOYSA-M tributyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CCCC)(CCCC)CCCC ANRASKQFUDPONQ-UHFFFAOYSA-M 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C08G18/28—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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
- C08G18/5015—Polyethers having heteroatoms other than oxygen having halogens having fluorine atoms
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14437599P | 1999-07-16 | 1999-07-16 | |
| US60/144,375 | 1999-07-16 | ||
| PCT/US2000/019097 WO2001005871A1 (en) | 1999-07-16 | 2000-07-13 | Amorphous polyether glycols based on bis-substituted oxetane monomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003524684A true JP2003524684A (ja) | 2003-08-19 |
| JP2003524684A5 JP2003524684A5 (enExample) | 2004-12-24 |
Family
ID=22508307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001511522A Pending JP2003524684A (ja) | 1999-07-16 | 2000-07-13 | ビス置換オキセタンモノマーを基剤としたアモルファスポリエーテルグリコール |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US6479623B1 (enExample) |
| EP (1) | EP1228121A1 (enExample) |
| JP (1) | JP2003524684A (enExample) |
| AU (1) | AU6095100A (enExample) |
| CA (1) | CA2379371A1 (enExample) |
| WO (1) | WO2001005871A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016088997A (ja) * | 2014-10-31 | 2016-05-23 | Nok株式会社 | ポリウレタンエラストマーの製造方法、ポリウレタンエラストマー、ｈｄｄストッパー、内部離型剤の使用及びポリウレタンエラストマー原料 |
| CN111484598A (zh) * | 2020-04-14 | 2020-08-04 | 中国铁道科学研究院集团有限公司铁道建筑研究所 | 一种高强度单组份隧道衬砌结构防护涂料 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020127420A1 (en) * | 1998-03-05 | 2002-09-12 | Weinert Raymond J. | Two stage thermoformable fluorinated polyoxetane-polyester copolymers |
| US7320829B2 (en) | 1998-03-05 | 2008-01-22 | Omnova Solutions Inc. | Fluorinated polymer and amine resin compositions and products formed therefrom |
| US7727436B2 (en) * | 1998-03-05 | 2010-06-01 | Omnova Solutions Inc. | Coating derived from polyesters crosslinked with melamine formaldehyde |
| US6673889B1 (en) * | 1999-06-28 | 2004-01-06 | Omnova Solutions Inc. | Radiation curable coating containing polyfuorooxetane |
| US6962966B2 (en) | 1999-12-28 | 2005-11-08 | Omnova Solutions Inc. | Monohydric polyfluorooxetane oligomers, polymers, and copolymers and coatings containing the same |
| US6403760B1 (en) | 1999-12-28 | 2002-06-11 | Omnova Solutions Inc. | Monohydric polyfluorooxetane polymer and radiation curable coatings containing a monofunctional polyfluorooxetane polymer |
| GB0025092D0 (en) * | 2000-10-13 | 2000-11-29 | Glaxo Group Ltd | Medicament dispenser |
| CA2447132C (en) | 2001-05-14 | 2008-10-07 | Omnova Solutions Inc. | Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups |
| US6855775B2 (en) * | 2001-12-13 | 2005-02-15 | Omnova Solutions Inc. | Polymeric blocks of an oxetane oligomer, polymer or copolymer, containing ether side chains terminated by fluorinated aliphatic groups, and hydrocarbon polymers or copolymers |
| US20040162381A1 (en) * | 2003-02-19 | 2004-08-19 | Dey Subir K. | Anti-graffiti composition |
| US7396590B2 (en) * | 2003-07-09 | 2008-07-08 | Virginia Commonwealth University | Soft block with repeat units that favor migration to a surface and repeat units with an activity of interest, and polymeric articles or coatings using same |
| US7771793B2 (en) * | 2003-07-09 | 2010-08-10 | Virginia Commonwealth University | Functional polymers via surface modifying agents, and methods for polymeric surface modification |
| TW200628515A (en) * | 2004-12-13 | 2006-08-16 | Omnova Solutions Inc | Polyether block copolymers |
| US20060135725A1 (en) * | 2004-12-21 | 2006-06-22 | Scimed Life Systems, Inc. | New balloon materials |
| US7608710B2 (en) * | 2005-06-07 | 2009-10-27 | Omnova Solutions Inc. | Cationic surfactants |
| US7420472B2 (en) * | 2005-10-16 | 2008-09-02 | Bao Tran | Patient monitoring apparatus |
| CN201461555U (zh) * | 2009-04-24 | 2010-05-12 | 东莞动利电子有限公司 | 风扇防尘防漏油结构 |
| US20130209735A1 (en) * | 2010-08-18 | 2013-08-15 | Higher Dimension Materials, Inc. | Protective material having guard plates with improved surface properties |
| JP5866179B2 (ja) * | 2011-11-10 | 2016-02-17 | イーストマン コダック カンパニー | 平版印刷版前駆体及び平版印刷版の作製方法 |
| US10248053B2 (en) | 2016-09-16 | 2019-04-02 | Xerox Corporation | Transfer assist members |
| US10191405B2 (en) * | 2016-11-11 | 2019-01-29 | Xerox Corporation | Electrostatic charging member |
| CN110770271B (zh) | 2017-05-19 | 2023-04-18 | 埃特纳科技有限公司 | 官能化氟化单体的制备方法、氟化单体及用于制备其的组合物 |
| CN120004874A (zh) * | 2023-09-28 | 2025-05-16 | 西安近代化学研究所 | 一种3,3-二（4-叠氮基呋咱-3-氧甲基）氧杂环丁烷及其合成方法 |
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| US2909492A (en) | 1954-06-15 | 1959-10-20 | Hercules Powder Co Ltd | Preparation of oxetane polymers |
| US2895924A (en) | 1956-08-27 | 1959-07-21 | Hercules Powder Co Ltd | Preparation of oxetane polymers |
| US2895921A (en) | 1956-08-27 | 1959-07-21 | Hercules Powder Co Ltd | Preparation of oxetane polymers |
| US2905647A (en) | 1956-08-27 | 1959-09-22 | Hercules Powder Co Ltd | Preparation of oxetane polymers |
| US2895931A (en) | 1958-03-31 | 1959-07-21 | Hercules Powder Co Ltd | Method for preparation of 3,3-disubstituted oxetane polymers |
| DE1495627A1 (de) | 1960-03-31 | 1970-03-19 | Hoechst Ag | Lineare Polyaether aus Oxacyclobutanderivaten,die in 3-Stellung durch halogenhaltige Gruppen disubstituiert sind,und Verfahren zu ihrer Herstellung |
| US3096344A (en) | 1961-05-09 | 1963-07-02 | Research Corp | Perfluoroalkyloxetanes |
| US3347801A (en) | 1962-11-16 | 1967-10-17 | Exxon Research Engineering Co | 3-difluoroaminomethyl-3-difluoroamino-oxetane and polymers thereof |
| DE1643323A1 (de) | 1967-07-06 | 1971-03-25 | Hoechst Ag | Disubstituierte Oxetane und Verfahren zu ihrer Herstellung |
| AU507270B2 (en) | 1975-01-28 | 1980-02-07 | Bell-Matic A/S | Slot machine |
| US4097046A (en) * | 1977-02-08 | 1978-06-27 | Elias Stewart Friant | Lacrosse stick |
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| US4414384A (en) | 1982-06-14 | 1983-11-08 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis and polymerization of 3-azidooxetane |
| US4675452A (en) | 1985-07-18 | 1987-06-23 | Lagow Richard J | Perfluorinated polyether fluids |
| US4827042A (en) | 1985-11-08 | 1989-05-02 | Exfluor Research Corporation | Perfluoropolyethers |
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| US4764586A (en) | 1986-10-29 | 1988-08-16 | Morton Thiokol, Inc. | Internally-plasticized polyethers from substituted oxetanes |
| US4847427A (en) | 1988-04-13 | 1989-07-11 | E. I. Du Pont De Nemours And Company | Process for preparing fluorocarbon polyethers |
| IT1217658B (it) | 1988-05-20 | 1990-03-30 | Ausimont Spa | Processo perfezionato per la produzione di perfluoropolieteri costituiti sostanzialmente da unita' perfludossietilenche e perfluoroossipropileniche |
| US4965342A (en) | 1988-06-03 | 1990-10-23 | Arizona Board Of Regents, Acting On Behalf Of Arizona State University | High molecular weight polymers and copolymers of 3-hydroxyoxetane and derivatives thereof |
| US4946992A (en) | 1988-06-20 | 1990-08-07 | Ciba-Geigy Corporation | Heteroatom containing perfluoroalkyl terminated neopentyl glycols and compositions therefrom |
| US4898981A (en) | 1988-06-20 | 1990-02-06 | Ciba-Geigy Corporation | Heteroatom containing perfluoroalkyl terminated neopentyl glycols and compositions therefrom |
| US4898987A (en) | 1989-03-17 | 1990-02-06 | Texaco Chemical Company | Method for production of phenol/acetone from cumene hydroperoxide |
| US4948992A (en) * | 1988-10-31 | 1990-08-14 | International Business Machines Corporation | Static method to negate offset voltages in CMOS operational amplifiers |
| US4970295A (en) | 1989-02-27 | 1990-11-13 | Arco Chemical Technology, Inc. | Preparation of oxetane polyether polyols using a bleaching earth catalyst |
| US4988797B1 (en) * | 1989-03-14 | 1993-12-28 | Cationic polymerization of cyclic ethers | |
| US4986797A (en) | 1989-04-03 | 1991-01-22 | Robert Nemirovsky | XY positioning apparatus |
| US5097048A (en) | 1989-11-30 | 1992-03-17 | Ciba-Geigy Corporation | Heteroatom containing 3,3-bis-perfluoroalkyl oxetanes and polyethers therefrom |
| US5463084A (en) | 1992-02-18 | 1995-10-31 | Rensselaer Polytechnic Institute | Photocurable silicone oxetanes |
| GB2269816B (en) * | 1992-07-10 | 1996-10-30 | Aerojet General Co | Preparation and polymerization of perfluoroalkoxy alkylene oxides to prepare hydrophobic polyethers |
| US5807977A (en) | 1992-07-10 | 1998-09-15 | Aerojet General Corporation | Polymers and prepolymers from mono-substituted fluorinated oxetane monomers |
| US5650453A (en) | 1995-04-28 | 1997-07-22 | General Electric Company | UV curable epoxysilicone blend compositions |
| US6383651B1 (en) * | 1998-03-05 | 2002-05-07 | Omnova Solutions Inc. | Polyester with partially fluorinated side chains |
-
2000
- 2000-07-13 CA CA002379371A patent/CA2379371A1/en not_active Abandoned
- 2000-07-13 JP JP2001511522A patent/JP2003524684A/ja active Pending
- 2000-07-13 WO PCT/US2000/019097 patent/WO2001005871A1/en not_active Ceased
- 2000-07-13 AU AU60951/00A patent/AU6095100A/en not_active Abandoned
- 2000-07-13 EP EP00947321A patent/EP1228121A1/en not_active Withdrawn
- 2000-07-13 US US09/615,160 patent/US6479623B1/en not_active Expired - Lifetime
-
2002
- 2002-11-08 US US10/291,139 patent/US6825316B2/en not_active Expired - Fee Related
-
2004
- 2004-11-29 US US10/999,362 patent/US6998460B2/en not_active Expired - Fee Related
-
2006
- 2006-02-13 US US11/353,689 patent/US7148309B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016088997A (ja) * | 2014-10-31 | 2016-05-23 | Nok株式会社 | ポリウレタンエラストマーの製造方法、ポリウレタンエラストマー、ｈｄｄストッパー、内部離型剤の使用及びポリウレタンエラストマー原料 |
| CN111484598A (zh) * | 2020-04-14 | 2020-08-04 | 中国铁道科学研究院集团有限公司铁道建筑研究所 | 一种高强度单组份隧道衬砌结构防护涂料 |
| CN111484598B (zh) * | 2020-04-14 | 2022-03-08 | 中国铁道科学研究院集团有限公司铁道建筑研究所 | 一种高强度单组份隧道衬砌结构防护涂料 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6479623B1 (en) | 2002-11-12 |
| US6998460B2 (en) | 2006-02-14 |
| AU6095100A (en) | 2001-02-05 |
| US20050154217A1 (en) | 2005-07-14 |
| EP1228121A1 (en) | 2002-08-07 |
| US7148309B2 (en) | 2006-12-12 |
| WO2001005871A1 (en) | 2001-01-25 |
| CA2379371A1 (en) | 2001-01-25 |
| US20060135729A1 (en) | 2006-06-22 |
| US6825316B2 (en) | 2004-11-30 |
| US20030158373A1 (en) | 2003-08-21 |
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