AU2005211523A1 - Structure comprising at least one polyethylene layer and at least one layer of barrier polymer - Google Patents
Structure comprising at least one polyethylene layer and at least one layer of barrier polymer Download PDFInfo
- Publication number
- AU2005211523A1 AU2005211523A1 AU2005211523A AU2005211523A AU2005211523A1 AU 2005211523 A1 AU2005211523 A1 AU 2005211523A1 AU 2005211523 A AU2005211523 A AU 2005211523A AU 2005211523 A AU2005211523 A AU 2005211523A AU 2005211523 A1 AU2005211523 A1 AU 2005211523A1
- Authority
- AU
- Australia
- Prior art keywords
- layer
- polyethylene
- barrier polymer
- polymer
- functional groups
- 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.)
- Abandoned
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- -1 polyethylene Polymers 0.000 title description 65
- 229920000642 polymer Polymers 0.000 title description 58
- 239000004698 Polyethylene Substances 0.000 title description 52
- 229920000573 polyethylene Polymers 0.000 title description 52
- 230000004888 barrier function Effects 0.000 title description 47
- 125000000524 functional group Chemical group 0.000 description 28
- 239000004593 Epoxy Substances 0.000 description 27
- 239000000178 monomer Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 229920001903 high density polyethylene Polymers 0.000 description 12
- 239000004700 high-density polyethylene Substances 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 11
- 239000002033 PVDF binder Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- 150000002118 epoxides Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- 229920007457 Kynar® 720 Polymers 0.000 description 7
- 229920002313 fluoropolymer Polymers 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000004734 Polyphenylene sulfide Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000069 polyphenylene sulfide Polymers 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- 239000004738 Fortron® Substances 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 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 2
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229920000092 linear low density polyethylene Polymers 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- 229920001684 low density polyethylene Polymers 0.000 description 2
- 239000004702 low-density polyethylene Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WFLOTYSKFUPZQB-OWOJBTEDSA-N (e)-1,2-difluoroethene Chemical group F\C=C\F WFLOTYSKFUPZQB-OWOJBTEDSA-N 0.000 description 1
- WLQXEFXDBYHMRG-UPHRSURJSA-N (z)-4-(oxiran-2-ylmethoxy)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCC1CO1 WLQXEFXDBYHMRG-UPHRSURJSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical compound FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- PCIUZPXMSXBQKY-UHFFFAOYSA-N 2-(cyclohex-2-en-1-yloxymethyl)oxirane Chemical compound C1OC1COC1CCCC=C1 PCIUZPXMSXBQKY-UHFFFAOYSA-N 0.000 description 1
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- NMSZFQAFWHFSPE-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxycarbonyl)but-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OCC1CO1 NMSZFQAFWHFSPE-UHFFFAOYSA-N 0.000 description 1
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 238000004435 EPR spectroscopy Methods 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 229920013633 Fortron Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C08L23/0869—Acids or derivatives thereof
- C08L23/0884—Epoxide containing esters
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- B32B1/00—Layered products having a general shape other than plane
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- B32B1/00—Layered products having a general shape other than plane
- B32B1/08—Tubular products
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- 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
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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
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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
- B32B2250/00—Layers arrangement
- B32B2250/03—3 layers
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- B32B2250/00—Layers arrangement
- B32B2250/05—5 or more layers
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- B32B2250/24—All layers being polymeric
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- B32B2250/40—Symmetrical or sandwich layers, e.g. ABA, ABCBA, ABCCBA
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- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
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- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
- B32B2307/3065—Flame resistant or retardant, fire resistant or retardant
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- B32B2307/70—Other properties
- B32B2307/714—Inert, i.e. inert to chemical degradation, corrosion
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- 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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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2439/00—Containers; Receptacles
- B32B2439/40—Closed containers
- B32B2439/60—Bottles
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- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
Description
P001 Section 29 Regulation 3.2(2)
AUSTRALIA
Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Application Number: Lodged: Invention Title: Structure comprising at least one polyethylene layer and at least one layer of barrier polymer The following statement is a full description of this invention, including the best method of performing it known to us: Field of the invention The present invention relates to a structure comprising at least one polyethylene layer and at least one layer of barrier polymer. These structures are of use, for example, in the manufacture of pipes, tanks, bottles and containers in which the layer of barrier polymer is in contact with the stored or transported fluid. The preceding objects can be manufactured by the usual techniques for the conversion of thermoplastic materials, such as coextrusion or coextrusion blow-moulding. The term "barrier" means, for example, that this layer does not allow the petrol used in motor vehicles to pass through or allows only a very small amount to pass through.
The prior art and the technical problem Polyethylene has barrier properties with regard to petrol but these properties are unsatisfactory for many uses. It is necessary for the structure to also comprise a layer of barrier polymer. However, the majority of barrier polymers are incompatible with polyethylene. Thus, it is necessary to position a tie layer between the polyethylene layer and the layer of barrier polymer. Polyethylenes which carry epoxy functional groups, such as, for example, glycidyl (meth)acrylate, are possible ties between polyethylene and a barrier material, such as PPS or a polyester. The abbreviation "PPS" denotes poly(phenylene sulphide). However, it is sometimes difficult to coextrude these materials and the peel strength is sometimes too low. It has now been found that a blend of a polyethylene carrying epoxy functional groups with a viscous polymer which is compatible with it is a very good tie.
Brief description of the invention The present invention relates to a structure successively comprising: a layer of barrier polymer, a tie layer comprising, the total being 100%: 0 1 to 80% of at least one polyethylene carrying epoxy functional groups, 99 to 20% of at least one viscous polymer compatible with the polyethylene carrying epoxy functional groups, 2 a polyethylene layer, the layers adhering in their respective contact zones.
According to an alternative form, the present invention relates to a structure successively comprising: a layer of barrier polymer, a tie layer comprising, the total being 100%: 1 to 80% of at least one polyethylene carrying epoxy functional groups, 99 to 20% of at least one viscous polymer compatible with the polyethylene carrying epoxy functional groups, a polyethylene layer, a tie layer comprising, the total being 100%: 1 to 80% of at least one polyethylene carrying epoxy functional groups, 99 to 20% of at least one viscous polymer compatible with the polyethylene carrying epoxy functional groups, a layer of barrier polymer, the layers adhering in their respective contact zones.
According to a preferred form, the viscous polymer compatible with the polyethylene carrying epoxy functional groups is a polyethylene.
According to one alternative form of the invention, if the viscous polymer compatible with the polyethylene carrying epoxy functional groups is a polyethylene and if the blend of this viscous polyethylene compatible with the polyethylene carrying epoxy functional groups has sufficient mechanical strength to be able to be coextruded with the barrier polymer, then it is possible to dispense with the polyethylene layer which is adjacent to the tie layer, that is to say that, in this alternative form, the structure successively comprises: either: a layer of barrier polymer, a tie layer comprising, the total being 100%: 1 to 80% of at least one polyethylene carrying epoxy functional groups, 99 to 20% of at least one viscous polyethylene compatible with the polyethylene carrying epoxy functional groups, the layers adhering.in their respective contact zones.
or: a layer of barrier polymer, a tie layer comprising, the total being 100%: 1 to 80% of at least one polyethylene carrying epoxy functional groups, 99 to 20% of at least one viscous polyethylene compatible with the polyethylene carrying epoxy functional groups, a layer of barrier polymer, the layers adhering in their respective contact zones.
This structure is of use in preparing devices for the storage or transfer of fluids, in particular in motor vehicles. The invention also relates to these devices.
These devices can be pipes, tanks, bottles or containers in which the layer of barrier polymer is in contact with the stored or transported fluid. These structures can comprise other layers composed of other materials.
Detailed description of the invention As regards the barrier polymer, mention may be made, by way of example, of PVDF. This term is used to denote PVDFs which are vinylidene fluoride (VDF) homopolymers and vinylidene fluoride (VDF) copolymers preferably comprising at least 50% by weight of VDF and at least one other monomer which is copolymerizable with VDF. The comonomer is advantageously fluorinated. It can be chosen, for example, from vinyl fluoride; trifluoroethylene (VF3); chlorotrifluoroethylene (CTFE); 1,2-difluoroethylene; tetrafluoroethylene (TFE); hexafluoropropylene (HFP); perfluoro(alkyl vinyl ether)s, such as perfluoro(methyl vinyl ether) (PMVE), perfluoro(ethyl vinyl ether) (PEVE) and perfluoro(propyl vinyl ether) (PPVE); perfluoro(1,3-dioxole); and perfluoro(2,2dimethyl-1,3-dioxole) (PDD). The optional comonomer is preferably chosen from chlorotrifluoroethylene (CTFE), hexafluoropropylene (HFP), trifluoroethylene (VF3) and tetrafluoroethylene (TFE).
Preferably, the PVDF comprises, by weight, at least 50% of VDF, more preferably at least 75% and better still at least 85%. The comonomer is advantageously HFP.
Mention may also be made of polyesters, such as PBT (poly(butylene terephthalate)), PEN (poly(ethylene naphthalate)) and PBN (poly(butylene naphthalate)).
Mention may also be made of polyketones, poly(dimethyl ketene)s and PPS.
Poly(dimethyl ketene)s are disclosed in patents EP 1 388 553, EP 1 002 819 and WO 04/044030.
The barrier polymer is not PVC nor polypropylene.
The barrier polymer can be functionalized in all or part, that is to say that the layer of barrier polymer comprises, the total being 100%, from 1 to 100% of functionalized barrier polymer and from 99 to 0% of barrier polymer.
Advantageously, the layer of barrier polymer comprises, the total being 100%, from 1 to 40% of functionalized barrier polymer and from 99 to 60% of barrier polymer. Preferably, the layer of barrier polymer comprises, the total being 100%, from 15 to 40% of functionalized barrier polymer and from 85 to 60% of barrier polymer.
According to another form of the invention, the layer of barrier polymer can be composed of two layers, one comprising a blend, the total being 100%, of 1 to 100% of functionalized barrier polymer and from 99 to 0% of barrier polymer, this layer being positioned against the tie layer, and the other composed of the barrier polymer.
According to an advantageous form of the invention, the layer of barrier polymer is composed of two layers, one comprising a blend, the total being 100%, of 1 to of functionalized barrier polymer and from 99 to 60% of barrier polymer, this layer being positioned against the tie layer, and the other composed of the barrier polymer.
According to a preferred form of the invention, the layer of barrier polymer is composed of two layers, one comprising a blend, the total being 100%, of 15 to of functionalized barrier polymer and from 85 to 60% of barrier polymer, this layer being positioned against the tie layer, and the other composed of the barrier polymer.
A functionalized barrier polymer is a barrier polymer comprising at least one polar groups (such as an epoxy group, an anhydride group, an acid group, a salt from an acid group) linked to the chains of the barrier polymer. As way of example, it can be mentioned a PVDF grafted by an unsaturated monomer or a copolymer of VDF and at least one unsaturated monomer (possibly along with another comonomer, in which case the polymer is a terpolymer).
The PVDF grafted by an unsaturated monomer can be manufactured according to a grafting process in which: a) the fluorinated polymer is melt blended with the unsaturated monomer, b) the blend obtained in a) is formed into films, sheets, granules or powders, c) the products from stage b) are subjected, in the absence of air, to photon irradiation or electron irradiation under a dose of between 1 and 15 Mrad, d) the product obtained in c) is optionally treated to remove all or part of the unsaturated monomer which has not been grafted to the fluorinated polymer.
As regards the unsaturated grafting monomer, mention may be made, by way of examples, of carboxylic acids and their derivatives, such as acid anhydrides, acid chlorides, isocyanates, oxazolines, epoxides, amines or hydroxides.
Preferably, the unsaturated monomer contains only one C=C double bond, ao as to avoid any cross-linking of the PVDF (leading to an increase of the viscosity and potential difficulties in extruding the material).
Examples of unsaturated carboxylic acids are those having 2 to 20 carbon atoms, such as acrylic acid, methacrylic acid, maleic acid, fumaric acid and itaconic acid. The functional derivatives of these acids comprise, for example, the anhydrides, the ester derivatives, the amide derivatives, the imide derivatives and the metal salts (such as the alkali metal salts) of the unsaturated carboxylic acids. Mention may also be made of undecylenic acid.
Unsaturated dicarboxylic acids having 4 to 10 carbon atoms and their functional derivatives, particularly their anhydrides, are particularly preferred grafting monomers. Maleic anhydride is preferred as it shows little homopolymerization and gives good adhesion values. The grafting of maleic anhydride is preferred as the copolymerization of VDF and maleic anhydride is not easily carried out with the current dispersed industrial processes (emulsion or suspension).
Stage a) is carried out in any blending device, such as extruders or mixers, used in the thermoplastics industry.
As regards the proportions of the fluorinated polymer and of the unsaturated monomer, the proportion of fluorinated polymer is advantageously, by weight, from 90 to 99.9% for respectively from 0.1 to 10% of unsaturated monomer.
Preferably, the proportion of fluorinated polymer is from 95 to 99.9% for respectively from 0.1 to 5% of unsaturated monomer.
On conclusion of stage it is found that the blend of the fluorinated polymer and of the unsaturated monomer has lost approximately from 10 to 50% of the 7 unsaturated monomer which had been introduced at the beginning of stage a).
This proportion depends on the volatility and on the nature of the unsaturated monomer. In fact, the monomer has been degassed in the extruder or the mixer and it is recovered in the vent lines.
As regards stage the products recovered on conclusion of stage b) are advantageously packed in polyethylene bags, the air is driven off and then they are closed. With regard to the irradiation method, use may be made, without distinction, of electron irradiation, better known under the name of 13 irradiation, and photon irradiation, better known under the name of y irradiation.
Advantageously, the dose is between 2 and 6 Mrad and preferably between 3 and 5 Mrad. Preferably, the source of irradiation is 60 cobalt bomb.
The grafting process takes place "cold" typically at temperatures below 1000C, or even below 500C, so that the PVDF/unsaturated monomer compound is not in the melt state, as in the case of a conventional grafting process carried out in an extruder. One essential difference is therefore that, in the case of a semicrystalline (as is the case with PVDF), the grafting takes place in the amorphous phase and not in the crystalline phase, whereas homogeneous grafting takes place in the case of melt grafting in an extruder. The unsaturated monomer is therefore not distributed along the PVDF chains in the same way in the case of radiation grafting as in the case of grafting carried out in an extruder.
As regards stage the ungrafted monomer can be removed by any means.
The proportion of grafted monomer with respect to the monomer present at the beginning of stage is between 50 and 100%. Washing can be carried out with solvents which are inert with respect to the fluorinated polymer and the grafted functional groups. For example, when maleic anhydride is grafted, washing can be carried out with chlorobenzene. It is also possible more simply to degas by placing the product recovered in stage c) under vacuum.
As regards the tie layer and first the polyethylene carrying epoxy functional groups, this can be a polyethylene to which epoxy functional groups have been grafted or a copolymer of ethylene and of an unsaturated epoxide.
As regards the copolymers of ethylene and of an unsaturated epoxide, mention may be made, for example, of copolymers of ethylene, of an alkyl (meth)acrylate and of an unsaturated epoxide or copolymers of ethylene, of a saturated carboxylic acid vinyl ester and of an unsaturated epoxide. These copolymers are prepared by a high pressure copolymerization process (P higher than 1000 bar). The amount of epoxide can be up to 15% by weight of the copolymer and the amount of ethylene at least 50% by weight.
Advantageously, the proportion of epoxide is between 2 and 12% by weight.
Advantageously, the proportion of alkyl (meth)acrylate is between 0 and and preferably between 5 and 35% by weight.
Advantageously, it is a copolymer of ethylene, of an alkyl (meth)acrylate and of an unsaturated epoxide. Preferably, the alkyl (meth)acrylate is such that the alkyl has 1 to 10 carbon atoms.
The examples of alkyl acrylate or methacrylate which can be used are in particular methyl methacrylate, methyl acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate or 2-ethylhexyl acrylate. Preferably, it is ethyl acrylate, butyl acrylate, methyl acrylate or 2-ethylhexyl acrylate.
The MFI (melt flow index) can be, for example, between 0.1 and 50 (g/10 min at 1900C under 2.16 kg).
Examples of unsaturated epoxides which can be used are in particular: aliphatic glycidyl esters and ethers, such as allyl glycidyl ether, vinyl glycidyl ether, glycidyl maleate, glycidyl itaconate, glycidyl acrylate and glycidyl methacrylate, and alicyclic glycidyl esters and ethers, such as 2-cyclohexen-l-yl glycidyl ether, diglycidyl glycidyl cyclohexene-4-carboxylate, glycidyl norbornene-2-carboxylate and diglycidyl endo-cisbicyclo[2.2.1 ]hept-5-ene-2,3-dicarboxylate.
Glycidyl methacrylate is preferred as it is easily copolymerized with ethylene and shows a good chemical reactivity.
As regards the tie layer and now the viscous polymer compatible with the polyethylene carrying epoxy functional groups, mention may be made of hydrogenated SBS block copolymers, such as, for example, SEBSs, EPRs, EPDMs and polyethylene. This polyethylene can be LDPE, LLDPE, HDPE and any polyethylene manufactured by any process, whether in the gas phase, in bulk or in solution and whether by Ziegler catalysis, by radical initiation or by metallocene catalysis (or monosite catalysis). Advantageously, the MFI (Melt Flow Index) of this compatible viscous polymer is between 0.1 and 1 g/10 min at 190 0 C and under 2.16 kg and preferably between 0.15 and 0.5. It is advantageously an HDPE.
With regard to the proportions of the constituants of the tie layer, they are: 1 to 80% of the polyethylene carrying epoxy functional groups, 99 to 20% of the viscous polymer compatible with the polyethylene carrying epoxy functional groups, advantageously: 10 to 50% of the polyethylene carrying epoxy functional groups, to 50% of the viscous polymer compatible with the polyethylene carrying epoxy functional groups, and preferably: to 40% of the polyethylene carrying epoxy functional groups, 90 to 60% of the viscous polymer compatible with the polyethylene carrying epoxy functional groups.
Advantageously, the MFI of the tie is between 0.15 and 1 g/10 minutes (measured at 1900C under 2.16 kg).
As regards the polyethylene layer, this polyethylene can be LDPE, LLDPE, HDPE and any polyethylene manufactured by any process, whether in the gas phase, in bulk or in solution and whether by Ziegler catalysis, by radical initiation or by metallocene catalysis (or monosite catalysis). It is advantageously HDPE as HDPE has excellent tensile and impact properties at temperatures as low as -500 C.
The structures of the invention can comprise other layers.
The structure can have any thickness. The thickness is, for example, between 100 pm and 25 mm.
As regards the alternative form in which the viscous polymer compatible with the polyethylene carrying epoxy functional groups is a polyethylene and in which the blend of this viscous polyethylene compatible with the polyethylene carrying epoxy functional groups has sufficient mechanical strength to be able to be coextruded with the barrier polymer, it has been seen that it is possible to dispense with the polyethylene layer which is adjacent to the tie layer.
Everything which has been described above, and in particular the composition of the tie, the composition of the barrier layer (or layers) and the nature of the products, is valid in this alternative form, except, of course, that which is specific to this alternative form. In fact, in this alternative form, the viscous polymer compatible with the polyethylene carrying epoxy functional groups is advantageously HDPE.
Examples The following polymers were used: Kynar® 720: PVDF homopolymer from Atofina and with an MVI (Melt Volume Index) of 10 cm 3 /10 min (2300C, 5 kg).
PVDF-1: PVDF homopolymer (Kynar® 720) grafted by maleic anhydride, grafted at 9000 ppm, with an MVI (Melt Volume Index) of 7cm 3 /10 min (measured at 230°C under 5 kg). The grafting was carried out through the irradiation with a cobalt 60 bomb of a mixture of Kynar 720 and maleic anhydride that was obtained with a twi-screw extruder at 230°C, 150 rpm with a mass flow-rate of 10 kg/h. The irradiation was carried out under 3 Mrad for 17 hours. After the irradiation step, the product is placed overnight under vacuum at 1300C to get free of the ungrafted maleic anhydride. The content of the grafted maleic anhydride (9000 ppm) was determined by infrared spectroscopy.
Lotader® 8840: copolymer of ethylene and of glycidyl methacrylate from Atofina and with an MVI (Melt Volume Index) of 5 cm 3 /10 min (190°C, 2.16 kg).
It comprises 92% of ethylene and 8% of glycidyl methacrylate by weight.
Finathene@ 3802 HDPE: denotes a high density polyethylene from Atofina with an MFI of 0.2 g/10 minutes under 2.16 kg at 190°C. Its density is 0.938.
Fortron® 0214: denotes a poly(phenylene sulphide) from Ticona with an MFI of 57 at 315°C, under 5 kg. Its density is 1.35.
Example 1 (according to the invention): The preparation is carried out, on an extruder of McNeil type, of a three layer structure composed, from the inside outwards, of a layer with a thickness of 300 p/m of a blend of 30% of PVDF-1 and of 70% of Kynar® 720, coextruded over a layer with a thickness of 100 pm of a blend obtained by dry blending, at the foot of the machine, 50% by weight of Lotader@ 8840 and 50% of Finathene® 3802 HDPE. This layer is itself coextruded over a layer with a thickness of 2.6 mm of Finathene@ 3802. The final structure exhibits an external diameter of 32 mm and a thickness of 3 mm. This coextrusion is carried out at a temperature of 240°C for each of the extruders used, and for the coextrusion head. The die is maintained at a temperature of 250°C. Peeling at t+24 hours (that is to say, 24 h after extrusion) gives an adhesive strength of 60 N/cm. The structure obtained does not exhibit any coextrusion defect; the internal surface is perfectly smooth, without any coextrusion corrugation.
Example 2 (comparative): The preparation is carried out, on an extruder of McNeil type, of a three layer structure composed, from the inside outwards, of a layer with a thickness of 300 pm of a blend of 30% of PVDF-1 and of 70% of Kynar® 720, coextruded over a layer with a thickness of 100 pm of Lotader® 8840. This layer is itself coextruded over a layer with a thickness of 2.6 mm of Finathene@ 3802. The final structure exhibits an external diameter of 32 mm and a thickness of 3 mm.
This coextrusion is carried out at a temperature of 240°C for each of the extruders used, and for the coextrusion head. The die is maintained at a temperature of 250°C. Peeling at t+24 hours give an adhesive strength of N/cm. The internal surface exhibits slight coextrusion corrugations.
Example 3 (comparative): The preparation is carried out, on an extruder of McNeil type, of a three layer structure composed, from the inside outwards, of a layer with a thickness of 300 pm of Fortron 0214, coextruded over a layer with a thickness of 100pm of Lotader® 8840. This layer is itself coextruded over a layer with a thickness of 2.6 mm of Finathene® 3802. The final structure exhibits an external diameter of 32 mm and a thickness of 3 mm. This coextrusion is carried out at a temperature of 3150C for the PPS extruder and 240°C for the other materials, and for the coextrusion head. The die is maintained at a temperature of 3150C.
Peeling at t+24 hours give an adhesive strength of 40 N/cm. The internal surface exhibits slight coextrusion corrugations.
Example 4 (according to the invention): The preparation is carried out, on an extruder of McNeil type, of a three layer structure composed, from the inside outwards, of a layer with a thickness of 300 pm of Fortron® 0214, coextruded over a layer with a thickness of 100 pm of a blend obtained by dry blending, at the foot of the machine, 50% by weight of Lotader 8840 and 50% of Finathene® 3802 HDPE. This layer is itself coextruded over a layer with a thickness of 2.6 mm of Finathene® 3802. The final structure exhibits an external diameter of 32 mm and a thickness of 3 mm.
This coextrusion is carried out at a temperature of 3150C for the PPS extruder and 2400C for the other materials, and for the coextrusion head. The die is maintained at a temperature of 3150C. Peeling at t+24 hours gives an adhesive strength of 45 N/cm. The structure obtained exhibits a few gel particles but no coextrusion defect; the internal surface is perfectly smooth, without any corrugation.
Example 5 (according to the invention): The preparation is carried out, on an extruder of McNeil type, of a three layer structure composed, from the inside outwards, of a layer with a thickness of 300 pm of a blend of 30% of PVDF-1 and of 70% of Kynar® 720, coextruded over a layer with a thickness of 100 pm of a blend obtained by dry blending, at the foot of the machine, 30% by weight of Lotader® 8840 and 70% of Finathene® 3802 HDPE. This layer is itself coextruded over a layer with a thickness of 2.6 mm of Finathene® 3802. The final structure exhibits an external diameter of 32 mm and a thickness of 3 mm. This coextrusion is carried out at a temperature of 240°C for each of the extruders used, and for the coextrusion head. The die is maintained at a temperature of 2500C. Peeling at t+24 hours gives an adhesive strength of 65 N/cm. The structure obtained does not exhibit any coextrusion defect; the internal surface is perfectly smooth, without any coextrusion corrugation.
Example 6 (according to the invention): The preparation is carried out, on an extruder of McNeil type, of a three layer structure composed, from the inside outwards, of a layer with a thickness of 300 pm of a blend of 30% of PVDF-1 and of 70% of Kynar® 720, coextruded over a layer with a thickness of 100 pm of a blend obtained by dry blending, at the foot of the machine, 15% by weight of Lotader® 8840 and 85% of Finathene® 3802 HDPE. This layer is itself coextruded over a layer with a thickness of 2.6 mm of Finathene@ 3802. The final structure exhibits an external diameter of 32 mm and a thickness of 3 mm. This coextrusion is carried out at a temperature of 2400C for each of the extruders used, and for the coextrusion head. The die is maintained at a temperature of 2500C. Peeling at t+24 hours gives an adhesive strength of 70 N/cm. The structure obtained does not exhibit any coextrusion defect; the internal surface is perfectly smooth, without any coextrusion corrugation.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR04.09755 | 2004-09-15 | ||
FR0409755A FR2875169B1 (en) | 2004-09-15 | 2004-09-15 | STRUCTURE COMPRISING AT LEAST ONE POLYETHYLENE LAYER AND AT LEAST ONE BARRIER POLYMER LAYER |
Publications (1)
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AU2005211523A1 true AU2005211523A1 (en) | 2006-03-30 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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AU2005211523A Abandoned AU2005211523A1 (en) | 2004-09-15 | 2005-09-14 | Structure comprising at least one polyethylene layer and at least one layer of barrier polymer |
Country Status (9)
Country | Link |
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EP (1) | EP1637319A1 (en) |
JP (1) | JP2006082554A (en) |
KR (2) | KR20060051359A (en) |
CN (1) | CN100491119C (en) |
AU (1) | AU2005211523A1 (en) |
BR (1) | BRPI0503819A (en) |
CA (1) | CA2519734A1 (en) |
FR (1) | FR2875169B1 (en) |
TW (1) | TWI266694B (en) |
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FR2906535A1 (en) * | 2006-10-03 | 2008-04-04 | Arkema France | Hot-melting adhesive composition based on a copolymer, comprising ethylene unit and polyisocyanate, resulting from reaction of ethylene copolymer and grafted/copolymerized unsaturated epoxy with carboxylic acid |
FR2908075B1 (en) * | 2006-11-07 | 2012-03-16 | Arkema France | MULTILAYER STRUCTURE BASED ON A BARRIER POLYMER POSSIBLY REINFORCED WITH IMPACT |
EP2460640B1 (en) | 2008-05-05 | 2014-08-27 | A. Schulman, Inc. | Multilayer clear over color polyolefin sheets and layered backing structure |
JP6163721B2 (en) * | 2012-09-12 | 2017-07-19 | 住友ベークライト株式会社 | Tire inner liner seat and tire |
WO2023161185A1 (en) * | 2022-02-24 | 2023-08-31 | Solvay Specialty Polymers Italy S.P.A. | Thermoplastic polymeric composition having good adhesion to polyolefin and fluoropolymer based materials |
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FR2659085B1 (en) * | 1990-03-02 | 1992-05-15 | Atochem | COMPOSITION COEXTRUDABLE WITH VINYLIDENE POLYFLUORIDE ALLOWING THE ADHESION OF THE SAME WITH A NON-COMPATIBLE POLYMERIC RESIN - COMPOSITE OBTAINED WITH THIS COMPOSITION. |
DE69431579T2 (en) * | 1993-08-03 | 2003-03-27 | Nitta Moore Co Ltd | Fuel transport tube |
US5427831B1 (en) * | 1993-11-12 | 1998-01-06 | Du Pont | Fluoropolymer laminates |
KR100229258B1 (en) * | 1993-12-13 | 1999-11-01 | 엘프 아토켐 소시에떼아노님 | Multilayer article including a valcanised elastomer directly combind with a thermoplastic |
DE4410148A1 (en) * | 1994-03-24 | 1995-09-28 | Huels Chemische Werke Ag | Multi-layer plastic tube |
EP0711658B1 (en) * | 1994-11-10 | 2002-10-23 | Sumitomo Chemical Company Limited | Multi-layer molded article and method for producing the same |
FR2786190B1 (en) | 1998-11-20 | 2003-07-18 | Atochem Elf Sa | POLY (DIMETHYLCETENE) BASED STRUCTURE, PACKAGING MATERIAL COMPRISING THE SAME |
FR2843116B1 (en) | 2002-08-02 | 2004-09-24 | Atofina | USE OF A POLY (DIMETHYLCETENE) BASED STRUCTURE AND OBJECTS COMPRISING THE SAME |
FR2846660B1 (en) | 2002-11-05 | 2006-07-07 | Atofina | CATIONIC CATALYSIS SYSTEM COMPRISING AN INITIATOR, CATALYST AND CO-CATALYST |
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2004
- 2004-09-15 FR FR0409755A patent/FR2875169B1/en not_active Expired - Fee Related
-
2005
- 2005-09-07 TW TW094130779A patent/TWI266694B/en not_active IP Right Cessation
- 2005-09-13 EP EP05291880A patent/EP1637319A1/en not_active Withdrawn
- 2005-09-13 BR BRPI0503819-7A patent/BRPI0503819A/en not_active IP Right Cessation
- 2005-09-14 AU AU2005211523A patent/AU2005211523A1/en not_active Abandoned
- 2005-09-15 JP JP2005267945A patent/JP2006082554A/en not_active Ceased
- 2005-09-15 KR KR1020050086498A patent/KR20060051359A/en not_active Application Discontinuation
- 2005-09-15 CA CA002519734A patent/CA2519734A1/en not_active Abandoned
- 2005-09-15 CN CNB2005101132121A patent/CN100491119C/en not_active Expired - Fee Related
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2007
- 2007-07-18 KR KR1020070071906A patent/KR20070088419A/en not_active Application Discontinuation
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TW200624257A (en) | 2006-07-16 |
EP1637319A1 (en) | 2006-03-22 |
BRPI0503819A (en) | 2006-04-25 |
FR2875169B1 (en) | 2008-07-04 |
KR20060051359A (en) | 2006-05-19 |
CA2519734A1 (en) | 2006-03-15 |
JP2006082554A (en) | 2006-03-30 |
CN1762698A (en) | 2006-04-26 |
FR2875169A1 (en) | 2006-03-17 |
TWI266694B (en) | 2006-11-21 |
KR20070088419A (en) | 2007-08-29 |
CN100491119C (en) | 2009-05-27 |
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