CA2327362C - Multi-layer compositions comprising a fluoropolymer - Google Patents
Multi-layer compositions comprising a fluoropolymer Download PDFInfo
- Publication number
- CA2327362C CA2327362C CA002327362A CA2327362A CA2327362C CA 2327362 C CA2327362 C CA 2327362C CA 002327362 A CA002327362 A CA 002327362A CA 2327362 A CA2327362 A CA 2327362A CA 2327362 C CA2327362 C CA 2327362C
- Authority
- CA
- Canada
- Prior art keywords
- fluorinated
- layer
- group
- substantially non
- base
- 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.)
- Expired - Fee Related
Links
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 82
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 69
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000000463 material Substances 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims abstract description 39
- 229920006120 non-fluorinated polymer Polymers 0.000 claims abstract description 34
- 239000000853 adhesive Substances 0.000 claims abstract description 30
- 230000001070 adhesive effect Effects 0.000 claims abstract description 30
- 125000003368 amide group Chemical group 0.000 claims abstract description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 75
- 239000002585 base Substances 0.000 claims description 64
- 239000004814 polyurethane Substances 0.000 claims description 46
- 229920002635 polyurethane Polymers 0.000 claims description 43
- 239000000178 monomer Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 25
- -1 hexafluoropropylene, tetrafluoroethylene Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 20
- 125000002015 acyclic group Chemical group 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 239000004952 Polyamide Substances 0.000 claims description 16
- 229920002647 polyamide Polymers 0.000 claims description 16
- 150000002500 ions Chemical class 0.000 claims description 13
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 10
- 239000001099 ammonium carbonate Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 10
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 9
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 9
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 9
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 6
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 5
- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 claims description 3
- RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 claims description 3
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 25
- 238000010276 construction Methods 0.000 abstract description 14
- 239000000446 fuel Substances 0.000 abstract description 9
- 239000002131 composite material Substances 0.000 abstract description 8
- 239000010410 layer Substances 0.000 description 162
- 229920001778 nylon Polymers 0.000 description 50
- 239000004677 Nylon Substances 0.000 description 49
- 239000010408 film Substances 0.000 description 39
- 239000008188 pellet Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000004744 fabric Substances 0.000 description 16
- 238000013329 compounding Methods 0.000 description 15
- 238000003825 pressing Methods 0.000 description 15
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 14
- 238000002156 mixing Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229920006264 polyurethane film Polymers 0.000 description 10
- 229920006284 nylon film Polymers 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 230000004888 barrier function Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000004962 Polyamide-imide Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229920001973 fluoroelastomer Polymers 0.000 description 5
- 239000004005 microsphere Substances 0.000 description 5
- 229920002312 polyamide-imide Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- 239000012790 adhesive layer Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920001601 polyetherimide Polymers 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229920005601 base polymer Polymers 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 241000206607 Porphyra umbilicalis Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003491 array Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical class OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920001470 polyketone Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229920006345 thermoplastic polyamide Polymers 0.000 description 2
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 description 1
- KQDQZEZWWRPNQH-UHFFFAOYSA-N 1,3-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1CN2 KQDQZEZWWRPNQH-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical class FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 1
- YTCHAEAIYHLXBK-UHFFFAOYSA-N 2-chloro-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Cl)C(F)(F)F YTCHAEAIYHLXBK-UHFFFAOYSA-N 0.000 description 1
- CFEMBVVZPUEPPP-UHFFFAOYSA-N 2-methylbuta-1,3-diene;prop-2-enenitrile Chemical compound C=CC#N.CC(=C)C=C CFEMBVVZPUEPPP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GVCWGFZDSIWLMO-UHFFFAOYSA-N 4-bromo-3,3,4,4-tetrafluorobut-1-ene Chemical compound FC(F)(Br)C(F)(F)C=C GVCWGFZDSIWLMO-UHFFFAOYSA-N 0.000 description 1
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 229920001780 ECTFE Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920006370 Kynar Polymers 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001312297 Selar Species 0.000 description 1
- 229920003365 Selar® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229920004738 ULTEM® Polymers 0.000 description 1
- 102220602575 Ubiquitin conjugation factor E4 A_C88A_mutation Human genes 0.000 description 1
- YGCODSQDUUUKIV-UHFFFAOYSA-N Zoxazolamine Chemical compound ClC1=CC=C2OC(N)=NC2=C1 YGCODSQDUUUKIV-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
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- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
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- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 150000002891 organic anions Chemical class 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
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- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
- C08J5/121—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives by heating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- 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
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- 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
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
-
- 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
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
-
- 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
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2848—Three or more layers
-
- 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
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- 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
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
- Y10T428/31544—Addition polymer is perhalogenated
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Laminated Bodies (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/058,421 | 1998-04-09 | ||
| US09/058,421 US6156400A (en) | 1998-04-09 | 1998-04-09 | Multi-layer compositions comprising a fluoropolymer |
| PCT/US1998/016865 WO1999052974A1 (en) | 1998-04-09 | 1998-08-12 | Multi-layer compositions comprising a fluoropolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2327362A1 CA2327362A1 (en) | 1999-10-21 |
| CA2327362C true CA2327362C (en) | 2008-02-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002327362A Expired - Fee Related CA2327362C (en) | 1998-04-09 | 1998-08-12 | Multi-layer compositions comprising a fluoropolymer |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6156400A (enExample) |
| EP (1) | EP1080140B1 (enExample) |
| JP (1) | JP2002511511A (enExample) |
| AU (1) | AU8906498A (enExample) |
| CA (1) | CA2327362C (enExample) |
| DE (1) | DE69814179T2 (enExample) |
| WO (1) | WO1999052974A1 (enExample) |
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| WO2000006376A1 (en) | 1998-07-30 | 2000-02-10 | Dyneon Llc | Composite articles including a fluoropolymer |
| WO2000052084A1 (en) * | 1999-03-02 | 2000-09-08 | 3M Innovative Properties Company | Compositions for fluoropolymer bonding to non-fluorinated polymers |
| US6417255B1 (en) * | 1999-12-15 | 2002-07-09 | General Electric Company | High performance thermoplastic compositions with improved melt flow behavior |
| US6767948B1 (en) | 1999-12-22 | 2004-07-27 | 3M Innovative Properties Company | Polyolefin polymer and catalyst blend for bonding fluoropolymers |
| CA2398147A1 (en) * | 2000-02-08 | 2001-08-16 | 3M Innovative Properties Company | Ink fixing materials and methods of fixing ink |
| US6293312B1 (en) * | 2000-05-23 | 2001-09-25 | Dayco Products, Inc. | Thermoplastic tubing |
| US8166969B2 (en) | 2001-03-06 | 2012-05-01 | Texas Research International, Inc. | Chemically and biologically resistant hydration system |
| US7141303B2 (en) * | 2001-03-06 | 2006-11-28 | 3M Innovative Properties Company | Protective articles |
| US7381666B2 (en) * | 2002-12-20 | 2008-06-03 | Kimberly-Clark Worldwide, Inc. | Breathable film and fabric having liquid and viral barrier |
| CN101352949A (zh) * | 2003-06-17 | 2009-01-28 | 大金工业株式会社 | 层积树脂成型体、层积树脂成型体制造方法及多层成型品 |
| US6986947B2 (en) * | 2003-10-09 | 2006-01-17 | 3M Innovative Properties Company | Method of modifying a fluoropolymer and articles thereby |
| US20050276944A1 (en) * | 2004-06-09 | 2005-12-15 | Muggli Mark M | Composite articles and methods of making the same |
| US20050276945A1 (en) * | 2004-06-09 | 2005-12-15 | Muggli Mark W | Composite articles and methods of making the same |
| US20050276985A1 (en) * | 2004-06-09 | 2005-12-15 | Muggli Mark W | Composite article having a tie layer and method of making the same |
| WO2006019922A1 (en) * | 2004-07-15 | 2006-02-23 | E.I. Dupont De Nemours And Company | Composition comprising ethylene-acrylate copolymer and polyolefin and tackifier |
| DE602005006573D1 (de) * | 2004-07-15 | 2008-06-19 | Du Pont | Zusammensetzung, enthaltend ethylencopolymere und polyolefine |
| US20060105285A1 (en) * | 2004-11-17 | 2006-05-18 | Naiyong Jing | Nonelastomeric dental article with a protective fluoropolymer layer |
| US20060105179A1 (en) * | 2004-11-17 | 2006-05-18 | Hofman Gerald R A | Elastomeric dental article with a protective fluoropolymer layer |
| US20080070182A1 (en) * | 2006-09-20 | 2008-03-20 | 3M Innovative Properties Company | Orthodontic elements and other medical devices with a fluorinated polymer, and methods |
| US8276785B1 (en) | 2008-04-19 | 2012-10-02 | D. Wheatley Enterprise, Inc. | NBC/CBRNE personal hydration system |
| US8524097B2 (en) * | 2009-03-18 | 2013-09-03 | Medtronic, Inc. | Plasma deposition to increase adhesion |
| US8361334B2 (en) * | 2009-03-18 | 2013-01-29 | Medtronic, Inc. | Plasma deposition to increase adhesion |
| BE1018516A3 (nl) * | 2009-03-30 | 2011-02-01 | Tekni Plex Europ Nv Nv | Werkwijze voor het vervaardigen van een meerlagige filmstructuur op basis van fluorpolymeren, en filmstructuur op deze wijze vervaardigd, alsook haar gebruik in de fotovolta¤sche toepassingen. |
| JP5936699B2 (ja) * | 2011-09-29 | 2016-06-22 | スリーエム イノベイティブ プロパティズ カンパニー | アミノ置換オルガノシランエステル触媒プライマー |
| CN102491993B (zh) * | 2011-11-24 | 2014-03-12 | 山东大学 | 一种三甲基硅醇锂的制备方法 |
| EP2620277A1 (de) | 2012-01-26 | 2013-07-31 | LANXESS Deutschland GmbH | Mehrschichtsysteme |
| CN108883617B (zh) * | 2016-04-01 | 2020-09-15 | 3M创新有限公司 | 多层含氟聚合物膜 |
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| US24906A (en) * | 1859-07-26 | Simeon goodfellow | ||
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| USRE24906E (en) | 1955-11-18 | 1960-12-13 | Pressure-sensitive adhesive sheet material | |
| US3190178A (en) * | 1961-06-29 | 1965-06-22 | Minnesota Mining & Mfg | Reflex-reflecting sheeting |
| US3467565A (en) * | 1961-07-27 | 1969-09-16 | Multifol Patentverwertungs Ag | Method of laminating a carrier web and a high melting plastic film |
| US4112213A (en) * | 1964-09-28 | 1978-09-05 | Johnson & Johnson | Pressure sensitive adhesive tapes and method of making same |
| US3551025A (en) * | 1969-03-28 | 1970-12-29 | Minnesota Mining & Mfg | Highly flexible reflex reflecting constructions |
| CA971093A (en) * | 1970-04-25 | 1975-07-15 | Yasuhiro Moriyama | Method for preparing laminated film of polymeric substances |
| US3689346A (en) * | 1970-09-29 | 1972-09-05 | Rowland Dev Corp | Method for producing retroreflective material |
| US4143204A (en) * | 1971-12-27 | 1979-03-06 | E. I. Du Pont De Nemours And Company | Articles coated with fluorocarbon resins |
| US4025159A (en) * | 1976-02-17 | 1977-05-24 | Minnesota Mining And Manufacturing Company | Cellular retroreflective sheeting |
| US4348312A (en) * | 1978-11-20 | 1982-09-07 | Minnesota Mining And Manufacturing Company | Ultra-high-index glass microspheres and products made therefrom with a fluoropolymer and an ester polymer blend |
| US4315045A (en) * | 1978-12-19 | 1982-02-09 | Crown City Plating Co. | Conditioning of polyamides for electroless plating |
| US4233421A (en) * | 1979-02-26 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition containing sulfonium curing agents |
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| JPH01177447A (ja) * | 1987-12-27 | 1989-07-13 | Toyoda Gosei Co Ltd | ダイヤフラム |
| US4912171A (en) * | 1988-04-01 | 1990-03-27 | Minnesota Mining And Manufacturing Company | Fluoroelastomer curing process with phosphonium compound |
| US5069964A (en) * | 1989-05-23 | 1991-12-03 | Minnesota Mining And Manufacturing Company | Flexible, substrate-insular retroreflective sheeting |
| US5112424A (en) * | 1989-09-01 | 1992-05-12 | Eastman Kodak Company | Low temperature multi-layer extrusion coating process |
| US5212279A (en) * | 1990-10-22 | 1993-05-18 | Hitachi Chemical Co., Ltd. | Hot-melt adhesive and its use in polyimide film and printed circuit board |
| US5441782A (en) * | 1991-07-16 | 1995-08-15 | Central Glass Company, Limited | Plastic laminate having polyamide resin surface layer and fluororesin surface layer |
| US5170011A (en) * | 1991-09-25 | 1992-12-08 | Teleflex Incorporated | Hose assembly |
| JPH085167B2 (ja) * | 1992-01-06 | 1996-01-24 | パイロット インダストリーズ、インコーポレイテッド | フルオロポリマー複合材料製チューブおよびその製造方法 |
| WO1993014933A1 (en) * | 1992-01-30 | 1993-08-05 | E.I. Du Pont De Nemours And Company | Laminar structure of polyimide and low melting fluoropolymer |
| US5383087A (en) * | 1992-04-14 | 1995-01-17 | Itt Corporation | Multi-layer fuel and vapor tube |
| US5284184A (en) * | 1992-04-14 | 1994-02-08 | Itt Corporation | Corrugated multi-layer tubing having at least one fluoroplastic layer |
| JPH0625617A (ja) * | 1992-07-08 | 1994-02-01 | Nitto Denko Corp | 粘着テープ |
| US5262490A (en) * | 1992-08-24 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| FR2699927B1 (fr) * | 1992-12-30 | 1995-02-03 | Hispano Suiza Sa | Procédé d'assemblage d'une première pièce en matériau composite réalisé en un polymère du type polyamide ou polyimide avec une deuxième pièce grâce à un adhésif approprié. |
| EP0637509B1 (en) * | 1993-08-03 | 2002-10-23 | Nitta Moore Company | A tube for fuel transportation |
| DE69429480T2 (de) * | 1993-09-09 | 2002-08-08 | Ausimont S.P.A., Mailand/Milano | Mehrschichtstrukturen aus fluorierten und nicht-fluorierten thermoplastischen Polymeren |
| WO1995011464A2 (en) * | 1993-10-20 | 1995-04-27 | Minnesota Mining And Manufacturing Company | Ultra-flexible retroreflective cube corner composite sheetings and methods of manufacture |
| US5450235A (en) * | 1993-10-20 | 1995-09-12 | Minnesota Mining And Manufacturing Company | Flexible cube-corner retroreflective sheeting |
| JPH09508079A (ja) * | 1994-01-24 | 1997-08-19 | ケムファブ コーポレイション | フルオロポリマーと熱的非粘着性非フルオロポリマーとの複合物及びその製造方法 |
| US5658670A (en) * | 1994-08-19 | 1997-08-19 | Minnesota Mining And Manufactury Company | Multi-layer compositions having a fluoropolymer layer |
| US5552199A (en) * | 1994-09-02 | 1996-09-03 | Minnesota Mining And Manufacturing Company | Melt-processable electroconductive fluoroplastic |
| JPH08281884A (ja) * | 1995-04-19 | 1996-10-29 | Mitsubishi Chem Corp | 積層体 |
| DE19537003A1 (de) * | 1995-10-04 | 1997-04-10 | Inventa Ag | Haftvermittler auf Polyamidbasis |
| US5591804A (en) * | 1995-12-21 | 1997-01-07 | Minnesota Mining And Manufacturing Company | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
| US5855977A (en) * | 1996-08-26 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Multi-layer compositions comprising a fluoropolymer |
| US6080487A (en) * | 1996-08-26 | 2000-06-27 | 3M Innovative Properties Company | Method of improving adhesion between a fluoropolymer and a substrate |
| US6165166A (en) * | 1997-04-25 | 2000-12-26 | Schneider (Usa) Inc. | Trilayer, extruded medical tubing and medical devices incorporating such tubing |
-
1998
- 1998-04-09 US US09/058,421 patent/US6156400A/en not_active Expired - Fee Related
- 1998-08-12 WO PCT/US1998/016865 patent/WO1999052974A1/en not_active Ceased
- 1998-08-12 DE DE69814179T patent/DE69814179T2/de not_active Expired - Fee Related
- 1998-08-12 EP EP98940887A patent/EP1080140B1/en not_active Expired - Lifetime
- 1998-08-12 AU AU89064/98A patent/AU8906498A/en not_active Abandoned
- 1998-08-12 CA CA002327362A patent/CA2327362C/en not_active Expired - Fee Related
- 1998-08-12 JP JP2000543526A patent/JP2002511511A/ja active Pending
-
2000
- 2000-09-28 US US09/676,196 patent/US6649005B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1080140A1 (en) | 2001-03-07 |
| EP1080140B1 (en) | 2003-05-02 |
| DE69814179T2 (de) | 2004-03-18 |
| WO1999052974A1 (en) | 1999-10-21 |
| DE69814179D1 (de) | 2003-06-05 |
| US6649005B1 (en) | 2003-11-18 |
| CA2327362A1 (en) | 1999-10-21 |
| US6156400A (en) | 2000-12-05 |
| AU8906498A (en) | 1999-11-01 |
| JP2002511511A (ja) | 2002-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |