JP4968338B2 - フッ素樹脂層とエラストマー層からなる積層体 - Google Patents
フッ素樹脂層とエラストマー層からなる積層体 Download PDFInfo
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- JP4968338B2 JP4968338B2 JP2009526487A JP2009526487A JP4968338B2 JP 4968338 B2 JP4968338 B2 JP 4968338B2 JP 2009526487 A JP2009526487 A JP 2009526487A JP 2009526487 A JP2009526487 A JP 2009526487A JP 4968338 B2 JP4968338 B2 JP 4968338B2
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- fluororesin
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- rubber
- elastomer
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- 229920001971 elastomer Polymers 0.000 title claims description 102
- 239000000806 elastomer Substances 0.000 title claims description 74
- 239000000446 fuel Substances 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 41
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 239000005060 rubber Substances 0.000 claims description 28
- -1 polyethylene Polymers 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 23
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 20
- 229920000647 polyepoxide Polymers 0.000 claims description 20
- 239000003822 epoxy resin Substances 0.000 claims description 19
- 229920000459 Nitrile rubber Polymers 0.000 claims description 14
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 8
- 150000001336 alkenes Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 229920005558 epichlorohydrin rubber Polymers 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 229920000573 polyethylene Polymers 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 3
- 229920000800 acrylic rubber Polymers 0.000 claims description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 93
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 125000000962 organic group Chemical group 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000013329 compounding Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
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- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 7
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- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 5
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- 238000005259 measurement Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 208000028659 discharge Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 150000004714 phosphonium salts Chemical group 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 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
- 230000003712 anti-aging effect Effects 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
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- 125000005067 haloformyl group Chemical group 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- ATPFMBHTMKBVLS-UHFFFAOYSA-N n-[6-(cinnamylideneamino)hexyl]-3-phenylprop-2-en-1-imine Chemical compound C=1C=CC=CC=1C=CC=NCCCCCCN=CC=CC1=CC=CC=C1 ATPFMBHTMKBVLS-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DXKZQNUSKZOLTC-UHFFFAOYSA-N 1,3,5-trichloro-2-[chloro-(2,4,6-trichlorophenoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1OP(Cl)(=O)OC1=C(Cl)C=C(Cl)C=C1Cl DXKZQNUSKZOLTC-UHFFFAOYSA-N 0.000 description 2
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- AZINJOAUEDYASP-UHFFFAOYSA-N 1-n,1-n'-diphenylethane-1,1-diamine Chemical compound C=1C=CC=CC=1NC(C)NC1=CC=CC=C1 AZINJOAUEDYASP-UHFFFAOYSA-N 0.000 description 2
- PVRZMTHMPKVOBP-UHFFFAOYSA-N 1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CNC1=CC=C(NC)C=C1 PVRZMTHMPKVOBP-UHFFFAOYSA-N 0.000 description 2
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 2
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- QMIWYOZFFSLIAK-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene Chemical compound FC(F)(F)C(=C)C(F)(F)F QMIWYOZFFSLIAK-UHFFFAOYSA-N 0.000 description 2
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- SCABKEBYDRTODC-UHFFFAOYSA-N bis[2-(2-butoxyethoxy)ethyl] hexanedioate Chemical compound CCCCOCCOCCOC(=O)CCCCC(=O)OCCOCCOCCCC SCABKEBYDRTODC-UHFFFAOYSA-N 0.000 description 2
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- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
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- KSMYREBPTSSZDR-UHFFFAOYSA-M tributyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC=C KSMYREBPTSSZDR-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L11/00—Hoses, i.e. flexible pipes
- F16L11/04—Hoses, i.e. flexible pipes made of rubber or flexible plastics
-
- 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
- B32B1/00—Layered products having a non-planar shape
- B32B1/08—Tubular products
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- 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
- B32B25/00—Layered products comprising a layer of natural or synthetic rubber
- B32B25/04—Layered products comprising a layer of natural or synthetic rubber comprising rubber as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B25/08—Layered products comprising a layer of natural or synthetic rubber comprising rubber 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B25/00—Layered products comprising a layer of natural or synthetic rubber
- B32B25/14—Layered products comprising a layer of natural or synthetic rubber comprising synthetic rubber copolymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
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- 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
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
-
- 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
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
- B32B27/322—Layered products comprising a layer of synthetic resin comprising polyolefins comprising halogenated polyolefins, e.g. PTFE
-
- 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
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
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- 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
- B32B2250/00—Layers arrangement
- B32B2250/24—All layers being polymeric
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- 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
- B32B2270/00—Resin or rubber layer containing a blend of at least two different polymers
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- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/50—Properties of the layers or laminate having particular mechanical properties
- B32B2307/546—Flexural strength; Flexion stiffness
-
- 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
- B32B2307/00—Properties of the layers or laminate
- B32B2307/70—Other properties
- B32B2307/726—Permeability to liquids, absorption
- B32B2307/7265—Non-permeable
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- 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
- B32B2597/00—Tubular articles, e.g. hoses, pipes
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- 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
- B32B2605/00—Vehicles
- B32B2605/08—Cars
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L11/00—Hoses, i.e. flexible pipes
- F16L11/04—Hoses, i.e. flexible pipes made of rubber or flexible plastics
- F16L2011/047—Hoses, i.e. flexible pipes made of rubber or flexible plastics with a diffusion barrier layer
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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
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1386—Natural or synthetic rubber or rubber-like compound containing
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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
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
- Y10T428/1393—Multilayer [continuous layer]
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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
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- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
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Description
1.基材の表面をサンドブラスター処理などで物理的に荒らす方法、
2.フッ素樹脂をナトリウム・エッチング、プラズマ処理、光化学的処理などの表面処理を行う方法、
3.接着剤を用いて接着させる方法、
などが主に検討されている。
エラストマー組成物から形成されるエラストマー層(b)
からなる積層体に関する。
で示される基、ハロホルミル基(−C(=O)X1、X1はハロゲン原子)、ホルミル基(−C(=O)H)、式(2):
で示される基、式:
で示される基、カルボキシル基(−C(=O)OH)、アルコキシカルボニル基(−C(=O)OR5(式中、R5は、炭素原子数1〜20の1価の有機基である))、アミド基(−C(=O)NR6R7(式中、R6およびR7は、同じであっても異なっていてもよく、水素原子または炭素原子数1〜20の1価の有機基である))、
式:
で示される基が好ましく、具体的には、−COOH、−OC(=O)OCH2CH2CH3、−COF、−OC(=O)OCH(CH3)2がより好ましい。
−CR8=CR9R10 (3)
R8、R9およびR10は、同じであっても異なっていてもよく、水素原子、フッ素原子または炭素原子数1〜20の1価の有機基である。式(3)の具体例としては、−CF=CF2、−CH=CF2、−CF=CHF、−CF=CH2、−CH=CH2などがあげられる。
−NR11R12 (4)
R11およびR12は、同じであっても異なっていてもよく、水素原子または炭素原子数1〜20の1価の有機基である。式(4)の具体例としては、−NH2、―NH(CH3)、−N(CH3)2、―NH(CH2CH3)、―N(C2H5)2、―NH(C6H5)などがあげられる。
CF2=CF−Rf 1 (5)
(式中、Rf 1は、−CF3または−ORf 2を表す。Rf 2は、炭素原子数1〜5のパーフルオロアルキル基を表す。)
で表されるパーフルオロエチレン性不飽和化合物などの1種または2種以上のパーフルオロオレフィン;クロロトリフルオロエチレン(以下、CTFEともいう)、トリフルオロエチレン、ヘキサフルオロイソブテン、フッ化ビニリデン(以下、VdFともいう)、フッ化ビニル、式(6):
CH2=CX2(CF2)nX3 (6)
(式中、X2は、水素原子またはフッ素原子を表し、X3は、水素原子、フッ素原子または塩素原子を表し、nは、1〜10の整数を表す。)
などのフルオロオレフィンなどをあげることができる。
(1)TFEとエチレンからなるエチレン−TFE共重合体(以下、ETFEともいう)
(2)TFEと式(5):
CF2=CF−Rf 1 (5)
(式中、Rf 1は、−CF3または−ORf 2を表す。Rf 2は、炭素原子数1〜5のパーフルオロアルキル基を表す。)
で表されるパーフルオロエチレン性不飽和化合物の1種または2種以上からなる、たとえばTFE−パーフルオロ(アルキルビニルエーテル)共重合体(PFA)またはTFE−ヘキサフルオロプロピレン(以下、HFPともいう)共重合体(FEP)
(3)TFE、エチレンおよび式(5):
CF2=CF−Rf 1 (5)
(式中、Rf 1は、−CF3または−ORf 2であり、Rf 2は、炭素数1〜5のパーフルオロアルキル基である)で表されるパーフルオロエチレン性不飽和化合物からなるエチレン−TFE−HFP共重合体、エチレン−TFE−パーフルオロエチレン性不飽和化合物共重合体
(4)ポリフッ化ビニリデン(PVDF)
(5)CTFE、TFEおよび式(5):
CF2=CF−Rf 1 (5)
(式中、Rf 1は、−CF3または−ORf 2であり、Rf 2は、炭素数1〜5のパーフルオロアルキル基である)で表されるパーフルオロエチレン性不飽和化合物からなるCTFE−TFE−パーフルオロエチレン性不飽和化合物共重合体
のいずれかであることが好ましく、(1)、(2)、(5)で表される含フッ素エチレン性重合体であることが好ましい。
ETFEの場合、前記の作用効果に加えて、力学物性や燃料バリア性が発現する点で好ましい。TFE単位とエチレン単位との含有モル比は20:80〜90:10が好ましく、38:62〜85:15がより好ましく、37:63〜80:20が特に好ましい。また、第3成分を含有していてもよく、第3成分としてはTFEおよびエチレンと共重合可能なものであればその種類は限定されない。第3成分としては、通常、下記式
CH2=CX3Rf 3、CF2=CFRf 3、CF2=CFORf 3、CH2=C(Rf 3)2
(式中、X3は水素原子またはフッ素原子、Rf 3はエーテル結合性酸素原子を含んでいてもよいフルオロアルキル基を表す)
で示されるモノマーが用いられ、これらの中でも、CH2=CX3Rf 3で示される含フッ素ビニルモノマーがより好ましく、Rf 3の炭素数が1〜8のモノマーが特に好ましい。
PFAまたはFEPの場合、前記の作用効果においてとりわけ耐熱性が優れたものとなり、また前記の作用効果に加えて優れた燃料バリア性が発現する点で好ましい。特に限定されないが、TFE単位70〜99モル%と式(5)で表されるパーフルオロエチレン性不飽和化合物単位1〜30モル%からなる共重合体であることが好ましく、TFE単位80〜97モル%と式(5)で表されるパーフルオロエチレン性不飽和化合物単位3〜20モル%からなる共重合体であることがより好ましい。TFE単位が70モル%未満では機械物性が低下する傾向があり、99モル%をこえると融点が高くなりすぎ成形性が低下する傾向がある。また、TFEおよび式(5)で表されるパーフルオロエチレン性不飽和化合物からなる含フッ素エチレン性重合体は、第3成分を含有していてもよく、第3成分としてはTFEおよび式(5)で表されるパーフルオロエチレン性不飽和化合物と共重合可能なものであればその種類は限定されない。
CTFE−TFE共重合体の場合、CTFE単位とTFE単位の含有モル比は、CTFE:TFE=2:98〜98:2であることが好ましく、5:95〜90:10であることがより好ましい。CTFE単位が2モル%未満であると薬液透過性が悪化しまた溶融加工が困難になる傾向があり、98モル%をこえると成型時の耐熱性、耐薬品性が悪化する場合がある。また、パーフルオロエチレン性不飽和化合物を共重合することが好ましく、CTFE単位とTFE単位の合計に対して、パーフルオロエチレン性不飽和化合物単位は0.1〜10モル%であり、CTFE単位およびTFE単位は合計で90〜99.9モル%であることが好ましい。パーフルオロエチレン性不飽和化合物単位が0.1モル%未満であると成形性、耐環境応力割れ性および耐ストレスクラック性に劣りやすく、10モル%をこえると薬液低透過性、耐熱性、機械特性、生産性などに劣る傾向にある。
で示される化合物、
式(8):
で示される化合物、および
式(9):
各種フッ素樹脂を金型にセットし、ヒートプレス機により、270〜300℃にて15〜30分保持し、動的架橋組成物を溶融状態にした後、3MPaの負荷を1分間与え圧縮成形し、所定の厚さのシート状試験片を作製した。
各種生ゴムに8インチオープンロールにて加硫剤、充填剤などの各種配合剤を添加し、フルコンパウンドを作製した。このフルコンパウンドをオープンロールにて所定の厚さのシート状試験片を作製した。
前記方法にて厚さ0.5mmのフッ素樹脂シートと厚さ1.5mmのゴム組成物シートを作製した。これらのシート試験片を重ね170℃に昇温した金型にセットし、ヒートプレス機により、170℃にて3MPaの負荷を20分与え、フッ素樹脂層―エラストマー層積層体を作製した。
得られた積層体をそれぞれ1.0cm幅×10cmの短冊状に切断して接着試験用試験片を作製し、この試験片について、オートグラフ((株)島津製作所製 AGS−J 5kN)を使用して、JIS−K−6256(加硫ゴムの接着試験方法)に記載の方法に準拠し、25℃において50mm/minの引張速度で剥離試験を行い、接着強度を測定した。また、剥離モードを観測し、以下の基準で評価した。
◎…フッ素樹脂層/エラストマー層界面は剥離せず、エラストマー層が材料破壊した。
○…フッ素樹脂層/エラストマー層界面で剥離したが、充分に接着しており剥離するのが困難であった。
△…フッ素樹脂層/エラストマー層界面で比較的容易に剥離した。
×…フッ素樹脂層とエラストマー層とが接着性を示さなかった。
前記の方法にて厚さ0.15〜0.30mmのシートを作製し、Perkin−Elmer FT−IRスペクトロメーター1760X(パーキンエルマー社製)を用いて赤外吸収スペクトルを分析した。得られた赤外吸収スペクトルをPerkin−Elmer Spectrum for windows Ver.1.4Cを用いて自動でベースラインを判定させ、所定のピークの吸光度を測定した。なお、フィルムの厚さはマイクロメーターを用いて測定した。
フッ素樹脂の共重合体組成は19F−NMRおよびフッ素の元素分析測定より求めた。
前記の方法で厚さ0.5mmのシート状試験片を作製した。20mLの容積を有するSUS製容器(開放部面積1.26×10-3m2)に模擬燃料であるCE10(トルエン/イソオクタン/エタノール=45/45/10容量%)を18mL入れて、前記シート状試験片を容器開放部にセットして密閉することで、試験体とする。該試験体を恒温装置(60℃)に入れ、試験体の重量を測定し、単位時間あたりの重量減少が一定となったところで下記の式により燃料透過係数を求めた。
前記方法で厚さ2mmのシート状試験片を作製し、ASTM V型ダンベルを用いて幅3.18mm標線間距離1.0mmのダンベル状試験片を打ち抜く。得られたダンベル状試験片を用いて、オートグラフ((株)島津製作所製 AGS−J 5kN)を使用して、ASTM D638に準じて、25℃において50mm/minの引張速度で引張試験を行った。
セイコー型示差走査熱量計〔DSC〕を用い、10℃/分の速度で昇温したときの融解ピークを記録し、極大値に対応する温度を融点とした。
メルトインデクサー(東洋精機製作所社製)を用い、各測定温度において、5kg荷重下で直径2mm、長さ8mmのノズルから単位時間(10分間)あたりに流出するポリマーの質量(g)を測定した。
実施例および比較例では、下記の材料を用いた。
(フッ素樹脂層)
フッ素樹脂(a−1):−COOH基を有するFEP。モノマー組成はTFE/HFP/パーフルオロ(プロピルビニルエーテル)=91.9/7.7/0.4(モル比)。融点260℃。372℃におけるMFRは18g/10min。−COOH基数は480個(炭素原子100万個当たり)。引っ張り弾性率は600MPa。燃料透過係数は0.3(g・mm)/(m2・day)。
エラストマー(b−1):FKMフルコンパウンド。3元フッ素ゴム生ゴム(G−558BP、ダイキン工業(株)製、VdF/TFE/HFP=58/20/22モル%)100質量部にビスフェノールAF(ダイキン工業(株)製)2.2質量部、DBU−B(和光純薬(株)製)0.56質量部、カーボンブラック(シーストS、東海カーボン(株)製)13質量部、酸化マグネシウム(キョーワマグ150、協和化学工業(株)製)3.0質量部、水酸化カルシウム(カルディック2000、近江化学工業(株)製)6.0質量部を添加し8インチオープンロールを用いて混練した。
表1および表2に示すフッ素樹脂層およびエラストマー層の組み合わせで、前記の方法にしたがい積層体を作製した。この積層体の接着強度を前記の方法により測定・評価した。このように、ポリマーの主鎖末端または側鎖にカルボニル基、オレフィン基またはアミノ基を有するフッ素樹脂から形成されるフッ素樹脂層(a)と、エラストマー組成物から形成されるエラストマー層(b)からなる積層体はその界面において良好な接着性を示し、燃料周辺用材料として有用であることがわかった。
Claims (7)
- ポリマーの主鎖末端または側鎖末端にカルボニル基、オレフィン基またはアミノ基を有するフッ素樹脂から形成されるフッ素樹脂層(a)と、
エラストマー組成物から形成されるエラストマー層(b)
からなる積層体であり、
前記フッ素樹脂層(a)におけるフッ素樹脂が、少なくとも1種の多官能化合物(c)を含有し、
該多官能化合物(c)が、分子内にアミノ基またはヒドロキシ基を有することを特徴とする積層体。 - フッ素樹脂層(a)におけるフッ素樹脂が、テトラフルオロエチレンとヘキサフルオロプロピレンからなる共重合体、エチレンとテトラフルオロエチレンからなる共重合体、またはクロロトリフルオロエチレンとテトラフルオロエチレンからなる共重合体である請求項1記載の積層体。
- エラストマー層(b)におけるエラストマー組成物が、アクリロニトリル−ブタジエンゴムまたはその水素添加ゴム、アクリロニトリル−ブタジエンゴムとポリ塩化ビニルとのブレンドゴム、フッ素ゴム、エピクロロヒドリンゴム、エチレン−プロピレンゴム、クロロスルホン化ポリエチレンゴムまたはアクリルゴムからなる請求項1または2記載の積層体。
- エラストマー層(b)におけるエラストマー組成物が、オニウム塩、アミン化合物、エポキシ樹脂よりなる群から選ばれる少なくとも1種の化合物を含有する請求項1〜3のいずれかに記載の積層体。
- 請求項1〜4のいずれかに記載の積層体から形成される成形品。
- 請求項1〜4のいずれかに記載の積層体から形成される燃料チューブ。
- 請求項1〜4のいずれかに記載の積層体の製造方法。
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CN103978751B (zh) * | 2013-02-08 | 2018-02-09 | 大金工业株式会社 | 层积体 |
EP3080601B1 (en) * | 2013-12-09 | 2018-09-26 | 3M Innovative Properties Company | A fluoroelastomer component for contacting ammonia and/or urea |
WO2016067627A1 (ja) | 2014-10-31 | 2016-05-06 | 株式会社Shindo | 積層シートおよびその製造方法 |
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JP6468074B2 (ja) * | 2015-05-26 | 2019-02-13 | Agc株式会社 | フッ素樹脂積層体およびその製造方法 |
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CN113423570B (zh) * | 2019-02-22 | 2024-05-14 | 大金工业株式会社 | 层压体 |
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- 2008-08-07 JP JP2009526487A patent/JP4968338B2/ja active Active
- 2008-08-07 US US12/673,374 patent/US20110287202A1/en not_active Abandoned
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2012
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Publication number | Publication date |
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WO2009020181A1 (ja) | 2009-02-12 |
EP2177353A1 (en) | 2010-04-21 |
US20120231196A1 (en) | 2012-09-13 |
JPWO2009020181A1 (ja) | 2010-11-04 |
EP2177353A4 (en) | 2010-08-25 |
EP2177353B1 (en) | 2014-10-22 |
US20110287202A1 (en) | 2011-11-24 |
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