WO2008137209A1 - Fluorinated poss as alloying agents in nonfluorinated polymers - Google Patents
Fluorinated poss as alloying agents in nonfluorinated polymers Download PDFInfo
- Publication number
- WO2008137209A1 WO2008137209A1 PCT/US2008/056611 US2008056611W WO2008137209A1 WO 2008137209 A1 WO2008137209 A1 WO 2008137209A1 US 2008056611 W US2008056611 W US 2008056611W WO 2008137209 A1 WO2008137209 A1 WO 2008137209A1
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- WIPO (PCT)
- Prior art keywords
- polymer
- nanostructured
- chemical
- blending
- nanostructured chemical
- Prior art date
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- 229920006120 non-fluorinated polymer Polymers 0.000 title claims abstract description 18
- 238000005275 alloying Methods 0.000 title abstract description 4
- 229920000642 polymer Polymers 0.000 claims abstract description 67
- 239000000126 substance Substances 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000002156 mixing Methods 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000000704 physical effect Effects 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 10
- 238000005299 abrasion Methods 0.000 claims abstract description 6
- 230000036962 time dependent Effects 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 41
- 239000000945 filler Substances 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002131 composite material Substances 0.000 claims description 9
- 238000013329 compounding Methods 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- 150000002739 metals Chemical class 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 230000035699 permeability Effects 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000005060 rubber Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims 2
- 230000007704 transition Effects 0.000 claims 2
- 239000003575 carbonaceous material Substances 0.000 claims 1
- 239000011243 crosslinked material Substances 0.000 claims 1
- 230000003628 erosive effect Effects 0.000 claims 1
- 238000000227 grinding Methods 0.000 claims 1
- 239000010954 inorganic particle Substances 0.000 claims 1
- 238000003801 milling Methods 0.000 claims 1
- 239000011146 organic particle Substances 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- 238000007740 vapor deposition Methods 0.000 claims 1
- 238000010348 incorporation Methods 0.000 abstract description 22
- 230000002787 reinforcement Effects 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 238000009736 wetting Methods 0.000 abstract description 4
- 238000007906 compression Methods 0.000 abstract description 3
- 230000006835 compression Effects 0.000 abstract description 3
- 238000004140 cleaning Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 16
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 15
- 239000004926 polymethyl methacrylate Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 9
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 238000004293 19F NMR spectroscopy Methods 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910004738 SiO1 Inorganic materials 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229920002313 fluoropolymer Polymers 0.000 description 6
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000002086 nanomaterial Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005341 cation exchange Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KBXJHRABGYYAFC-UHFFFAOYSA-N octaphenylsilsesquioxane Chemical compound O1[Si](O2)(C=3C=CC=CC=3)O[Si](O3)(C=4C=CC=CC=4)O[Si](O4)(C=5C=CC=CC=5)O[Si]1(C=1C=CC=CC=1)O[Si](O1)(C=5C=CC=CC=5)O[Si]2(C=2C=CC=CC=2)O[Si]3(C=2C=CC=CC=2)O[Si]41C1=CC=CC=C1 KBXJHRABGYYAFC-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 3
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229910020381 SiO1.5 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910001411 inorganic cation Inorganic materials 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 230000003075 superhydrophobic effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910021135 KPF6 Inorganic materials 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- XBGNERSKEKDZDS-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]acridine-4-carboxamide Chemical compound C1=CC=C2N=C3C(C(=O)NCCN(C)C)=CC=CC3=CC2=C1 XBGNERSKEKDZDS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000005374 siloxide group Chemical group 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- -1 tetramethyl ammonium Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/18—Plasticising macromolecular compounds
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N70/00—Solid-state devices having no potential barriers, and specially adapted for rectifying, amplifying, oscillating or switching
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
Definitions
- This invention relates generally to methods for enhancing the properties of nonfluorinated thermoplastic and thermoset polymers and particulate and filler surfaces through the addition of fluorine containing POSS nanostructured chemicals.
- the fluorinated component may be contained inside the POSS cage, external to the POSS cage or copolymerized with POSS cages. Additionally fluorinated POSS cages may contain metal atoms to improve their compatibility with polymers and surfaces and to impart catalytic activity.
- This invention also relates to processes and applications of polymeric materials and composites with improved physical properties and function that resemble those of conventional fluorinated materials. These properties and applications include improved surface properties, non-wetting, anti-icing, and low friction surfaces, biological activity, permeation control, fire retardancy, improve time-dependent mechanical properties which include (heat distortion, high temperature stability, compression set, creep, color retention, biological compatibility). BACKGROUND OF THE INVENTION
- polymers can be tailored to a high degree through variables such as polymer sequence, structure, additive and filler incorporation, composition, morphology, thermodynamic and kinetic processing control. It is similarly known that various sizes and shapes of fillers, and particulates (e.g. Teflon ® , calcium carbonate, silica, carbon black, etc.) can be incorporated into polymers, monomer mixtures, and composites to enhance physical properties.
- fillers, and particulates e.g. Teflon ® , calcium carbonate, silica, carbon black, etc.
- Prior art in nonfluoropolymers has utilize fluorinated additives and fluorinated filler particulates to impart characteristics of the fluorinated entity to the nonfluorinated polymer.
- the prior art suffers from process complexity, inappropriate length scale of the reinforcement to access polymer free volume, or the reinforcement lacks sufficient geometrical definition to provide structural regularity and reinforcement at the molecular (10 10 m) and nanoscopic (10 9 m) length scales. Consequently many desirable properties of the nonfluorinated polymer are lost upon incorporation of conventional fluorinated components.
- fluorinated nanostructured chemicals onto the surface of a secondary material (such as TiO 2 , CaCO 3 , glass or mineral fillers, and fibers) can be utilized to creating more surface area on such particle and improve their compatibility with fluorinated and nonfluorinated polymers.
- a secondary material such as TiO 2 , CaCO 3 , glass or mineral fillers, and fibers
- Recent developments in nanoscience have enabled the cost effective manufacture of commercial quantities of materials that are best described as nanostructured chemicals due to their specific chemical formula, hybrid (inorganic- organic) chemical composition, geometrically precise and rigid shape, large physical size relative to traditional chemicals (0.3-0.5 nm), and small physical size relative to larger sized traditional fillers (>50 nm).
- Nanostructured chemicals are best exemplified by those based on low-cost Polyhedral Oligomeric Silsesquioxanes (POSS) and Polyhedral Oligomeric Silicates .
- Figures 4, 5, 6 illustrate some representative examples of fluorinated nanostructured chemicals, which are also referred to as fluorinated POSS in this application. It is recognized that oligomeric, polymeric, and metal containing versions of fluorinated POSS may also be utilized.
- Nanostructured chemicals based on polyhedral oligomeric silsesquioxanes and polyhedral metallosesquioxanes are discussed in detail in U.S. Patent Nos. 5,412,053; 5,484,867; 6,329,490; and 6,716,919, which are expressly incorporated herein by reference in their entirety.
- the present invention describes methods of preparing new compositions by incorporating fluorinated-nanostructured chemicals into nonfluorinated polymers.
- the resulting nano-alloyed polymers are wholly useful by themselves or in combination with other polymers or in combination with macroscopic reinforcements such as fiber, clay, glass, mineral and other fillers and fibers.
- the nano-alloyed polymers are particularly useful for producing polymeric compositions with desirable physical properties such processing aids, surface lubricity, adhesion to polymeric surfaces, composite and metal surfaces, water repellency, reduced melt viscosity, reduced surface energy, low dielectric constant, resistance to abrasion and fire, biological compatibility, optical quality plastics, cosmetic applications.
- compositions presented herein contain three primary material combinations: (1 ) fluorinated nanostructured chemicals, fluorinated-nanostructured oligomers, or fluorinated-nanostructured polymers from the chemical classes of fluorine containing polyhedral oligomeric silsesquioxanes, polysilsesquioxanes, polyhedral oligomeric silicates, polysilicates, polyoxometallates, carboranes, boranes, and fluorinated polymorphs of carbon; (2) nonfluorinated polymer systems such as aromatic and aliphatics, semicrystalline, crystalline, glassy, elastomeric, oils, and lubricants thereof as derived from hydrocarbons, or silicones and copolymers thereof; and (3) inorganics metals, and particulate minerals and silicatious powders, and all forms of carbon including diamond powder, graphite, carbon black, tubes, spheres, mesophase, pitch, and fiber.
- the method of incorporating nanostructured chemicals into nonfluoropolymers is accomplished via blending of the fluorinated nanostructured chemicals with the nonfluorinated materials. All types and techniques of coating, blending, including melt blending, dry blending, solution blending, reactive and nonreactive blending are effective.
- selective incorporation of a nanostructured chemical into a specific region of a polymer can be accomplished by compounding into the polymer a nanostructured chemical with a chemical potential (miscibility) compatible with the chemical potential of the region desired within the material.
- a chemical potential miscibility
- the internally fluorinate cages 7 Cation[(RSiOi s) ⁇ @ F] ⁇ are particularly useful for incorporation into polar polymers (such as hydrogels because they are also polar and hence exhibit compatibility.
- the physical size of POSS cages in combination with tailorable compatibility enables fluorinated POSS to be selectively incorporated into polymers, composites, metals, ceramics and biological materials to control the surface topology, surface properties, and chain dynamics and subsequently favorably impact a multitude of physical properties.
- Properties most favorably improved are surface properties, including contact angle, coefficient of friction, anti-icing, surface tension, hydrophobicity, and lubricity.
- Other properties improved include time dependent mechanical and thermal properties such as heat distortion, heat stability, creep, compression set, shrinkage, modulus, hardness, and abrasion resistance.
- other physical properties are favorably improved, including thermal conductivity, refractive index, fire resistance, oxygen permeability, oxidative stability, electrical properties, printability and biological compatibility and activity.
- FIG 1 illustrates diameter and volume contributions for [(C-C 6 HnSiOi 5 )8 ] ⁇ 8 POSS cage.
- FIG 2 illustrates the surface area contribution for [(C-C 6 H 11 SiOi 5 ) 8 ] ⁇ 8 POSS cage relative to wt % loading.
- FIG. 3 illustrates the volume contribution for [(C-C 6 Hn SiO 1 . 5 ) ⁇ ] ⁇ 8 POSS cage relative to wt % loading.
- FIG. 4 illustrates representative examples of externally fluorinated POSS nanostructured chemicals.
- FIG. 5 illustrates representative examples of internally fluorinated POSS nanostructured chemical which also contain a counter cation to balance charge and assert additional compatibility.
- FIG. 6 illustrates a representative example of partially externally fluorinated POSS nanostructured chemical.
- FIG. 7 illustrates the contact angles for polystyrene showing increasing contact angle with [(CF 3 (CF 2 )7(CH2)2SiO 1 .5)8] ⁇ 8 POSS incorporation.
- FIG. 8 illustrates the contact angles for LDPE showing increasing contact angle with [(CF 3 (CF 2 )7(CH 2 )2SiOi. 5 )8] ⁇ 8 POSS incorporation.
- FIG. 9 illustrates the contact angles for styrene acrylonitrile showing increasing contact angle with [(CF 3 (CF 2 )7(CH2)2SiOi.5)8] ⁇ 8 POSS incorporation.
- FIG. 10 illustrates the contact angles for polymethylmethacrylate showing increasing contact angle with [(CF 3 (CF 2 )7(CH 2 )2SiOi.5)8] ⁇ 8 and (CH3)4N[(CF3(CF 2 )7(CH2)2SiOi. 5 )8@F] ⁇ 8 POSS incorporation.
- Polysilsesquioxanes may be either homoleptic or heteroleptic. Homoleptic systems contain only one type of R group while heteroleptic systems contain more than one type of R group.
- POSS and POS nanostructure compositions are represented by the formula:
- R is the same as defined above and X includes but is not limited to OH, Cl, Br, I, F, alkoxide (OR), acetate (OOCR), peroxide (OOR), amine (NR2) isocyanate (NCO), and R.
- m and n refer to the stoichiometry of the composition.
- the symbol ⁇ indicates that the composition forms a nanostructure and the symbol # refers to the number of silicon atoms contained within the nanostructure.
- the value for # is usually the sum of m+n, where n ranges typically from 1 to 24 and m ranges typically from 1 to 12.
- ⁇ # is not to be confused as a multiplier for determining stoichiometry, as it merely describes the overall nanostructural characteristics of the system (aka cage size).
- the symbol @ is also used in association with the POSS formula representations and indicates the presence of an F anion inside of the cage cavity.
- the present invention teaches the use of fluorinated POSS nanostructured chemicals as agents for imparting the characteristics of a fluorinated material (such as polymers) to nonfluorinated polymers, composites, additives, metals, and all types of particles.
- a fluorinated material such as polymers
- the keys that enable POSS nanostructured chemicals to impart fluorinated characteristics to such a diverse number of materials are: (1 ) their unique size with respect to polymer chain dimensions, and (2) their ability to be compatibilized with polymer systems to overcome forces that promote incompatibility and expulsion of the nanoreinforcing agent by polymer chains and surfaces and (3) their ability to bind to dissimilar surfaces.
- nanoscopic size of the POSS cage imparts these properties to materials at very small loading amounts and affords POSS to dominate the surface and volume characteristics of materials.
- ⁇ G ⁇ H-T ⁇ S
- ⁇ S entropic dispersion
- fluoropolymers are known for their hydrophobicity, low surface energy, and low coefficients of friction
- the incorporation of fluorinated POSS has been shown in US Patent No. 7,193,015 to further improve these properties in fluorinated polymers. Therefore extension of fluorinated POSS into nonfluorinated systems is a logical means for cost-effectively attaining such properties in nonfluorinated polymers.
- Blending processes such as melt blending, dry blending and solution mixing blending are all effective at mixing and alloying nanostructured chemical into plastics.
- Water contact angles are a measure of surface hydrophobicity and provide insight into the free energy of the surface.
- Critical surface tension of the POSS, POSS polymers, and POSS blends were determined.
- the surface tension of the fluid is graphed in relation to its contact angle on the surface. It should be noted that a surface with a contact angle of 90° or higher is considered a “non-wetting" surface, while a surface with a contact angle below 90° is considered “wetting.”
- F @ POSS cages can be controlled through variation of the R group on the cage and through variation of the counter cation associated with the cage. Numerous advantages can be realized by exchanging nonreactive onium cations such as tetramethyl ammonium, and tetrabutyl ammonium with onium cations containing reactive groups capable of polymerization, catalytic activity, wetability, color and pigmentation properties, radiation absorbance, biological activity, or therapeutic properties. Such functional activity is highly desired for the practical utility of F@ POSS.
- Onium exchange can be carried out by dissolving tetramethylammonium octaphenyl octasilsesquioxane fluoride (Me) 4 Nt(PhSiO 1 S ) 8 O F] 18 into THF followed by addition of a stoichiometrically equivalent amount of cetyltrimethyl ammonium chloride and stirring for 10 minutes at 25 0 C. Then 50ml of hexane was added to the mixture to form a second layer into which the resulting Cetyl(Me) 3 N[(PhSiO 1 5 ) 8 @ F] ⁇ 8 was extracted. Upon removal of volatiles and drying a quantitative amount of product was obtained. The Cetyl(Me) 3 N[(PhSi0i. 5 ) 8 @ F] ⁇ 8 was observed to be significantly more effective as a biocidal agent that the tetramethylammonium cation.
- Me tetramethylammonium octaphen
- cation exchange of the onium groups on F@ POSS with an inorganic cation such as K+, Na+, Li+, Ag+ is desirable as they afford higher temperature stability and do not produce a noticeable smell when heated.
- Onium exchange for inorganic cations was successfully accomplished for example, by addition of KPF6 to a THF solution of tetramethylammonium octaphenyl octasilsesquioxane fluoride (Me) 4 NI(PhSiO 1 S ) 8 O F]Ji 8 .
- Copolymers of hepta ⁇ rifluoropropyOpropylmethylmethacrylate octamer POSS [(CF3(CH 2 ) 3 SiOi.5)7(propylmethacrylate)SiOi 5)i] ⁇ a) and methylmethacrylate were prepared using the following general procedure.
- fluorinated POSS cages also bearing reactive groups are desirable for surface modification of metals, fillers, and composites can be prepared.
- Preferred reactive groups include but are not limited to silanols, siloxides, methacrylates, thiols, amines, acids, esters, alcohols, isocyanates, epoxides, and Lewis acidic metals. Incorporation of Fluorinated POSS Cages into Nonfluorinated Polymers.
- fluorinated POSS cages can be prepared and potentially incorporated into polymers and the proper selection of POSS cage is dependent upon its compatibility with the desired polymer. Also of importance is the surface properties of the cage. For example fluorinated POSS cages exhibiting low surface energy, high water contact angle, with low powder density and crystal density are desired. Table 2 contains as summary of preferred systems for incorporation into polymers.
- PMMA Increasing the hydrophobicity of PMMA is highly desirable as water absorption by PMMA is well known to reduce its durability and aesthetics for signage, utensils and optical applications.
- PMMA is widely utilized in dental and prosthetic application, paints, adhesives, and coatings in which the uptake of moisture causes degradation of mechanical properties.
- the contact angles for a series of these blends were measured after annealing for 2 hours at 140 0 C (Table 3) and after annealing for 2 hours at 175°C (Table 4).
- Nonfluorinated thermoplastics were obtained from a variety of commercial suppliers. The melting and processing temperature for each polymer was determined by differential scanning calorimetry (DSC), Externally and internally fluorinated POSS were prepared as described. A general method for incorporation of the POSS into the thermoplastic polymer utilized a twin screw extruder (MicroCompounder, DACA Instruments) and compounding of the polymer and POSS thoroughly until a steady-state of mixer torque was observed.
- DSC differential scanning calorimetry
- Thermosetting polymers can similarly be utilized in which the POSS is incorporated via both high and low shear mixing and copolymerization.
- the preferred method is dependent upon the visual homogenization of the system and the viscosity of the initial resin mixture.
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Abstract
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EP08780474A EP2125908A4 (en) | 2007-03-19 | 2008-03-12 | Fluorinated poss as alloying agents in nonfluorinated polymers |
JP2009554641A JP2010522264A (en) | 2007-03-19 | 2008-03-12 | Fluorinated POSS as an alloying agent in non-fluorinated polymers |
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CN101657473B (en) | 2013-01-02 |
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US7897667B2 (en) | 2011-03-01 |
US20080221262A1 (en) | 2008-09-11 |
EP2125908A4 (en) | 2010-11-10 |
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