JP2005534771A - フッ素化ポリマー - Google Patents
フッ素化ポリマー Download PDFInfo
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- JP2005534771A JP2005534771A JP2004526018A JP2004526018A JP2005534771A JP 2005534771 A JP2005534771 A JP 2005534771A JP 2004526018 A JP2004526018 A JP 2004526018A JP 2004526018 A JP2004526018 A JP 2004526018A JP 2005534771 A JP2005534771 A JP 2005534771A
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- block copolymer
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- 229920002313 fluoropolymer Polymers 0.000 title description 6
- 239000000178 monomer Substances 0.000 claims abstract description 107
- 229920001400 block copolymer Polymers 0.000 claims abstract description 75
- 229920000642 polymer Polymers 0.000 claims abstract description 72
- 125000000524 functional group Chemical group 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims description 69
- 239000000463 material Substances 0.000 claims description 56
- -1 alkyl methacrylates Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 22
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 9
- 150000002924 oxiranes Chemical class 0.000 claims description 9
- 239000006260 foam Substances 0.000 claims description 8
- 229920005604 random copolymer Polymers 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- 150000003440 styrenes Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920000307 polymer substrate Polymers 0.000 claims description 3
- 229920000428 triblock copolymer Polymers 0.000 claims description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
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- 238000006243 chemical reaction Methods 0.000 description 42
- 239000003999 initiator Substances 0.000 description 35
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 31
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- 230000015572 biosynthetic process Effects 0.000 description 17
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 238000003786 synthesis reaction Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 11
- 238000005984 hydrogenation reaction Methods 0.000 description 11
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 9
- 241000628997 Flos Species 0.000 description 8
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- 238000002360 preparation method Methods 0.000 description 8
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- 125000006239 protecting group Chemical group 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- BEIWUHUHJDEMQO-UHFFFAOYSA-N 2-[methyl(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)amino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BEIWUHUHJDEMQO-UHFFFAOYSA-N 0.000 description 6
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
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- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
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- 230000000171 quenching effect Effects 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229920000359 diblock copolymer Polymers 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- JMSAQNDFUOUWPU-UHFFFAOYSA-N 2-methylbuta-1,3-diene;2-[methyl(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)amino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C=C.CC(=C)C(=O)OCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JMSAQNDFUOUWPU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- 230000009977 dual effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical class CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000005211 surface analysis Methods 0.000 description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 238000006276 transfer reaction Methods 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- OGBWMWKMTUSNKE-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CCCCCC(OC(=O)C(C)=C)OC(=O)C(C)=C OGBWMWKMTUSNKE-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229920003350 Spectratech® Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- 238000002835 absorbance Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 2
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- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- UUQLCJCZFWUWHH-UHFFFAOYSA-N lithium;1-phenylhexylbenzene Chemical compound [Li+].C=1C=CC=CC=1[C-](CCCCC)C1=CC=CC=C1 UUQLCJCZFWUWHH-UHFFFAOYSA-N 0.000 description 2
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 2
- 238000010551 living anionic polymerization reaction Methods 0.000 description 2
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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- 239000000376 reactant Substances 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
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- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
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- RYGFDWHDMQEQMB-UHFFFAOYSA-N 1,2,3-tris(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CCl)=C1CCl RYGFDWHDMQEQMB-UHFFFAOYSA-N 0.000 description 1
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- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
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- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 235000013175 Crataegus laevigata Nutrition 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
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
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- YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 description 1
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- FYOQEFGAZKEPGG-UHFFFAOYSA-N [Li]C1=CC=C(C)C=C1 Chemical compound [Li]C1=CC=C(C)C=C1 FYOQEFGAZKEPGG-UHFFFAOYSA-N 0.000 description 1
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- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 1
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- VMRZYTKLQVKYKQ-UHFFFAOYSA-N lithium;1,9-dihydrofluoren-1-ide Chemical compound [Li+].C1=C[C-]=C2CC3=CC=CC=C3C2=C1 VMRZYTKLQVKYKQ-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- BONOXOHRDYVMPV-UHFFFAOYSA-N lithium;prop-1-en-2-ylbenzene Chemical compound [Li].CC(=C)C1=CC=CC=C1 BONOXOHRDYVMPV-UHFFFAOYSA-N 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- DQDWATOXYCARFV-UHFFFAOYSA-M magnesium;2-methanidylpropane;bromide Chemical compound [Mg+2].[Br-].CC(C)[CH2-] DQDWATOXYCARFV-UHFFFAOYSA-M 0.000 description 1
- UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
- WSHFRLGXCNEKRX-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CC[CH-]C WSHFRLGXCNEKRX-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing atoms other than carbon or hydrogen
- C08L23/0869—Copolymers of ethene with unsaturated hydrocarbons containing atoms other than carbon or hydrogen with unsaturated acids, e.g. [meth]acrylic acid; with unsaturated esters, e.g. [meth]acrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/005—Modified block copolymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/005—Modified block copolymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
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- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
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| US10/211,096 US6903173B2 (en) | 2002-08-02 | 2002-08-02 | Fluorinated polymers |
| PCT/US2003/020944 WO2004013225A1 (en) | 2002-08-02 | 2003-07-03 | Fluorinated polymers |
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| JP2005534771A true JP2005534771A (ja) | 2005-11-17 |
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| EP (1) | EP1527135A1 (enExample) |
| JP (1) | JP2005534771A (enExample) |
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| MX (1) | MXPA05001161A (enExample) |
| WO (1) | WO2004013225A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007186671A (ja) * | 2005-12-13 | 2007-07-26 | Agc Seimi Chemical Co Ltd | 界面活性剤および表面張力低下方法 |
| JP2008266490A (ja) * | 2007-04-23 | 2008-11-06 | Tokyo Institute Of Technology | Ｎ−メタクリロイルアゼチジン系ブロック共重合体 |
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| AU1440901A (en) * | 1999-10-27 | 2001-05-08 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
| WO2003082303A1 (en) * | 2002-03-29 | 2003-10-09 | Wisconsin Alumni Research Foundation | Polymeric micelle formulations of hydrophobic compounds and methods |
| US7632916B2 (en) * | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| US7402625B2 (en) * | 2003-06-11 | 2008-07-22 | 3M Innovative Properties Company | Compositions and method for improving the processing of polymer composites |
| US8236874B2 (en) * | 2003-06-11 | 2012-08-07 | 3M Innovative Properties Company | Compositions and method for improving the processing of polymer composites |
| EP1732485A2 (en) * | 2004-01-02 | 2006-12-20 | Wisconsin Alumni Research Foundation | Encapsulation of chemical compounds in fluorous-core and fluorous-inner-shell micelles formed from semifluorinated-block or fluorinated-block copolymers |
| US6969491B1 (en) | 2004-09-01 | 2005-11-29 | 3M Innovative Properties Company | Stirred tube reactor and method of using the same |
| EP1632464B1 (en) * | 2004-09-02 | 2011-04-13 | 3M Innovative Properties Company | Method for treating porous stone using a fluorochemical composition |
| US7691932B2 (en) * | 2004-09-27 | 2010-04-06 | 3M Innovative Properties Company | Method of making a composition and nanocomposites therefrom |
| US7329702B2 (en) * | 2004-09-27 | 2008-02-12 | 3M Innovative Properties Company | Composition and method of making the same |
| US7495051B2 (en) * | 2004-09-27 | 2009-02-24 | 3M Innovative Properties Company | Nanocomposite and method of making the same |
| BRPI0517820A (pt) * | 2004-11-16 | 2008-10-21 | 3M Innovative Properties Co | composição, e, método |
| US8193270B2 (en) * | 2004-12-14 | 2012-06-05 | 3M Innovative Properties Company | Method of making composites and nanocomposites |
| US7495118B2 (en) | 2004-12-30 | 2009-02-24 | 3M Innovative Properties Company | Compositions containing C4-swallow tail silanes |
| US7160850B2 (en) | 2004-12-30 | 2007-01-09 | 3M Innovative Properties Company | Compositions of monomeric surfactants |
| US7776983B2 (en) * | 2004-12-30 | 2010-08-17 | 3M Innovative Properties Company | Fluorochemical polymeric surfactants |
| BRPI0606959A2 (pt) * | 2005-02-23 | 2017-06-13 | 3M Innovative Properties Co | mescla polimérica |
| ES2453566T3 (es) * | 2005-08-26 | 2014-04-08 | Kuraray Co., Ltd. | Composición de elastómero termoplástico y artículo moldeado compuesto fabricado a partir de la misma |
| US20070135577A1 (en) * | 2005-12-09 | 2007-06-14 | Shefelbine Terri A | Intermediate elastomer compositions |
| EP1960839A4 (en) * | 2005-12-16 | 2012-01-11 | Arkema Inc | METHOD AND APPLICATIONS FOR PRODUCING BLOCK COPOLYMERS WITH LOW SURFACE ENERGY |
| US7629298B2 (en) * | 2006-02-21 | 2009-12-08 | 3M Innovative Properties Company | Sandstone having a modified wettability and a method for modifying the surface energy of sandstone |
| US7569715B2 (en) * | 2006-07-05 | 2009-08-04 | 3M Innovative Properties Company | Compositions containing silanes |
| WO2008070490A2 (en) * | 2006-11-28 | 2008-06-12 | Wisconsin Alumni Research Foundation | Fluoropolymer-based emulsions for the intravenous delivery of fluorinated volatile anesthetics |
| US20080139722A1 (en) * | 2006-12-08 | 2008-06-12 | 3M Innovative Properties Company | Vibration damping polymer composites |
| US8900562B2 (en) * | 2007-01-12 | 2014-12-02 | Wisconsin Alumni Research Foundation | Semi-fluorinated block copolymers for delivery of therapeutic agents |
| KR20100126785A (ko) * | 2008-03-04 | 2010-12-02 | 코넬 유니버시티 | 삼중블록 폴리머 및 폴리머 코팅 |
| US8809209B2 (en) | 2010-12-17 | 2014-08-19 | E I Du Pont De Nemours And Company | Fluorinated copolymers |
| EP3497172A4 (en) * | 2016-08-10 | 2020-02-26 | 3M Innovative Properties Company | FLUORED TAPE MAKER FOR ADHESIVE ADHESIVES AND ADHESIVE ITEMS |
| EP3336112A1 (en) * | 2016-12-19 | 2018-06-20 | 3M Innovative Properties Company | Fluoroalkyl (meth)acrylate polymers and compositions |
| EP4526357A1 (en) * | 2022-05-18 | 2025-03-26 | University of Houston System | Fluorinated polymerization catalysts and methods of making and using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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-
2002
- 2002-08-02 US US10/211,096 patent/US6903173B2/en not_active Expired - Fee Related
-
2003
- 2003-07-03 CA CA 2494333 patent/CA2494333A1/en not_active Abandoned
- 2003-07-03 BR BR0313119A patent/BR0313119A/pt not_active IP Right Cessation
- 2003-07-03 EP EP20030742423 patent/EP1527135A1/en not_active Withdrawn
- 2003-07-03 KR KR1020057001860A patent/KR20050030969A/ko not_active Withdrawn
- 2003-07-03 MX MXPA05001161A patent/MXPA05001161A/es unknown
- 2003-07-03 AU AU2003281868A patent/AU2003281868A1/en not_active Abandoned
- 2003-07-03 CN CNA03823212XA patent/CN1685010A/zh active Pending
- 2003-07-03 JP JP2004526018A patent/JP2005534771A/ja not_active Withdrawn
- 2003-07-03 WO PCT/US2003/020944 patent/WO2004013225A1/en not_active Ceased
-
2004
- 2004-11-24 US US10/997,468 patent/US20050154142A1/en not_active Abandoned
- 2004-11-24 US US10/997,471 patent/US20050154071A1/en not_active Abandoned
-
2006
- 2006-10-05 US US11/538,962 patent/US20070100006A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007186671A (ja) * | 2005-12-13 | 2007-07-26 | Agc Seimi Chemical Co Ltd | 界面活性剤および表面張力低下方法 |
| JP2008266490A (ja) * | 2007-04-23 | 2008-11-06 | Tokyo Institute Of Technology | Ｎ−メタクリロイルアゼチジン系ブロック共重合体 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070100006A1 (en) | 2007-05-03 |
| AU2003281868A1 (en) | 2004-02-23 |
| CN1685010A (zh) | 2005-10-19 |
| BR0313119A (pt) | 2005-07-05 |
| CA2494333A1 (en) | 2004-02-12 |
| US20040023016A1 (en) | 2004-02-05 |
| US20050154142A1 (en) | 2005-07-14 |
| KR20050030969A (ko) | 2005-03-31 |
| US20050154071A1 (en) | 2005-07-14 |
| US6903173B2 (en) | 2005-06-07 |
| MXPA05001161A (es) | 2005-05-16 |
| EP1527135A1 (en) | 2005-05-04 |
| WO2004013225A1 (en) | 2004-02-12 |
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