WO2000064647A1 - Fermetures traitees - Google Patents
Fermetures traitees Download PDFInfo
- Publication number
- WO2000064647A1 WO2000064647A1 PCT/AU2000/000365 AU0000365W WO0064647A1 WO 2000064647 A1 WO2000064647 A1 WO 2000064647A1 AU 0000365 W AU0000365 W AU 0000365W WO 0064647 A1 WO0064647 A1 WO 0064647A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copolymer
- cork
- coating
- substrate
- active
- Prior art date
Links
- 238000000576 coating method Methods 0.000 claims abstract description 63
- 239000007799 cork Substances 0.000 claims abstract description 60
- 239000011248 coating agent Substances 0.000 claims abstract description 49
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 36
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000009792 diffusion process Methods 0.000 claims abstract description 17
- 230000004888 barrier function Effects 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 11
- 235000013334 alcoholic beverage Nutrition 0.000 claims abstract description 9
- 235000013361 beverage Nutrition 0.000 claims abstract description 8
- 235000013305 food Nutrition 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- -1 polyethylene terephthalate Polymers 0.000 claims description 37
- 229920001577 copolymer Polymers 0.000 claims description 27
- 239000004698 Polyethylene Substances 0.000 claims description 24
- 229920000573 polyethylene Polymers 0.000 claims description 24
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 12
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 12
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 9
- 239000005001 laminate film Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000005062 Polybutadiene Substances 0.000 claims description 5
- 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 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 4
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 3
- 229920000554 ionomer Polymers 0.000 claims description 3
- 230000035699 permeability Effects 0.000 claims description 3
- 229920000298 Cellophane Polymers 0.000 claims description 2
- 239000000020 Nitrocellulose Substances 0.000 claims description 2
- 229930182556 Polyacetal Natural products 0.000 claims description 2
- 229920002367 Polyisobutene Polymers 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims description 2
- 229920001220 nitrocellulos Polymers 0.000 claims description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920001195 polyisoprene Polymers 0.000 claims description 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 claims description 2
- CLYZNABPUKUSDX-UHFFFAOYSA-N trichloromethoxybenzene Chemical class ClC(Cl)(Cl)OC1=CC=CC=C1 CLYZNABPUKUSDX-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 claims 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 claims 1
- 230000001953 sensory effect Effects 0.000 description 23
- 238000011156 evaluation Methods 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000012360 testing method Methods 0.000 description 18
- 235000014101 wine Nutrition 0.000 description 16
- 239000010410 layer Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000010408 film Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000007766 curtain coating Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000386 microscopy Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000004291 sulphur dioxide Substances 0.000 description 2
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000001029 thermal curing Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- 235000020097 white wine Nutrition 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 description 1
- 239000000592 Artificial Cell Substances 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 229920001986 Vinylidene chloride-vinyl chloride copolymer Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- UFRKOOWSQGXVKV-UHFFFAOYSA-N ethene;ethenol Chemical compound C=C.OC=C UFRKOOWSQGXVKV-UHFFFAOYSA-N 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000002081 peroxide group Chemical group 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B67—OPENING, CLOSING OR CLEANING BOTTLES, JARS OR SIMILAR CONTAINERS; LIQUID HANDLING
- B67B—APPLYING CLOSURE MEMBERS TO BOTTLES JARS, OR SIMILAR CONTAINERS; OPENING CLOSED CONTAINERS
- B67B1/00—Closing bottles, jars or similar containers by applying stoppers
- B67B1/03—Pretreatment of stoppers, e.g. cleaning, steaming, heating, impregnating or coating; Applying resilient rings to stoppers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D51/00—Closures not otherwise provided for
- B65D51/005—Closures provided with linings or internal coatings so as to avoid contact of the closure with the contents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
- B27K3/153—Without in-situ polymerisation, condensation, or cross-linking reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K7/00—Chemical or physical treatment of cork
Definitions
- This invention provides improved closures for use in connection with food or beverages.
- One application is in relation to closures for wine bottles.
- corks made from natural cork material.
- this material can be subject to initial flaws, or deteriorate in use, resulting in contamination or spoilage of the wine.
- oxidation of the wine due to permeation of oxygen through the cork into the wine, results in vinegar flavour.
- vinegar flavour due to the presence of trichloro-anisoles (TCA) and other undesirable flavour-active or odour-active compounds in the cork, imparts a musty or mouldy smell and flavour to the wine.
- TCA trichloro-anisoles
- Leakage can also be a problem.
- cork is a relatively expensive material, as most supplies still come from Portugal.
- Synthetic "corks” and screw-cap stoppers have been used in the wine industry, but have not yet been tested adequately over the prolonged storage periods of quality red wines. There is some indication, however, that synthetic "corks” may impart flat flavours to wines. Furthermore, there is considerable consumer resistance to use of synthetic "corks” and screw-cap stoppers, particularly for quality wines. A further disadvantage is that synthetic "corks” are generally far more difficult to remove, using a hand-operated corkscrew, than natural corks.
- the first cork coatings were simply lubricants such as paraffin and Vaseline. These merelv ensured that the cork was easier to insert into the bottle and later remove, without disintegration. The other problems associated with cork stoppers were not addressed.
- materials used in surface treatment of corks include oils and silicone resins, emulsions of various formulations, as well as some synthetic coatings. These coatings do prevent leakage of the wine, but do not provide a barrier against taint and oxidation.
- Hybrid corks have been moulded from natural cork and synthetic cork cells made from a synthetic polymer.
- the synthetic cells fill the gaps between the cork cells, and a binding agent (such as polyurethane) is used to bind the cells together.
- a binding agent such as polyurethane
- hybrid corks have to date proved unsatisfactory, as they often leak and can disintegrate and be difficult to extract from a bottle.
- the present invention provides an improved closure having a surface coating or diffusion layer comprising an appropriate polymer.
- This coating or diffusion layer has many properties which are of benefit when used (for example) in relation to corks (either natural or synthetic) for wine bottles.
- the coating or diffusion layer limits oxygen permeability, inhibits or prevents the diffusion of rrichloro-anisoles (TCA) and other flavour-active or odour-active compounds from the cork to the alcoholic beverage, adheres strongly to the cork and/ or penetrates into the surface of the cork, is sufficiently flexible to be capable of withstanding compression and decompression during the corking process, enables the coated cork to be readily extracted from the bottle, reduces or prevents wine leakage, is resistant to sulphur dioxide, and has long life under alcoholic beverage conditions.
- TCA rrichloro-anisoles
- These coatings or diffusion layers are also applicable to substrates other than cork (eg packaging and wrapping materials) which are in contact with food products or beverages.
- an appropriate polymer which forms a physical barrier to gases (eg oxygen) and flavour-active or odour-active compounds (eg TCA), is applied as a surface coating or diffusion layer to a substrate for use in contact with food products or beverages.
- gases eg oxygen
- flavour-active or odour-active compounds eg TCA
- Polymeric materials the molecular structure and/ or morphology of which help to prevent permeation of gases and vapours (such as oxygen) and flavour-active or odour-active compounds (commonly know as taint compounds), can be classed as barrier polymers.
- Barrier polymers with low oxygen permeability see RTajima, A.Banba, M. Takanori, T.
- the present invention provides a method for producing a coating or diffusion layer on a substrate (eg a cork) for use in contact with a food product or beverage, said coating or diffusion layer preventing or inhibiting passage therethrough (eg from a cork to an alcoholic beverage) of flavour-active or odour-active compounds, and said method comprising applying to the surface of said substrate an effective amount of a barrier polymer, said barrier polymer being a polymeric material, the molecular structure and/ or morphology of which prevents or inhibits passage therethrough (eg from a cork to an alcoholic beverage) of flavour-active or odour-active compounds.
- the present invention provides a coated substrate, and in particular a coated natural or synthetic cork, produced according to that method.
- the substrate may, for example, be a bottle closure (such as a cork), packaging and wrapping materials (such as packaging for cheese), or a bottle or other container.
- a bottle closure such as a cork
- packaging and wrapping materials such as packaging for cheese
- the polymer is selected so as to form a physical barrier to the passage of gases and flavour-active or odour-active compounds.
- the polymer coating or diffusion layer of the present invention will prevent any flavour- active or odour-active compounds migrating from a cork to an alcoholic beverage. It must also adhere strongly to the substrate and/ or penetrate into the surface of the substrate, and be sufficiently flexible for its proposed use (eg to withstand compression and decompression during the corking process, if the substrate is a cork).
- the polymer coating or diffusion layer must enable the coated cork to be readily extracted from the bottle, prevent wine leakage, and have long life under alcoholic beverage conditions.
- the polymer coating or diffusion layer will also be resistant to sulphur dioxide and changes in pH.
- Polymers which may be used include: polyurethane and copolymers and ionomers polyethylene terephthalate (PET) polyethylene vinyl alcohol polyvinyl alcohol polyacrylonitrile and copolymers, eg styrene-acrylonitrile and acrylonitrile- butadiene-styrene (ABS) polyvinylidene chloride (PVDC) and copolymers polyvinylchloride and copolymers Cellophane Saran (a vinylidene chloride-vinyl chloride copolymer) epoxy polymers siloxane copolymers, eg comprising polyethylene glycol (PEG), isoprene, butadiene, lactone, amino, terephthalate, amino acid, heterocyclic, hydride
- SiH thiol or epoxy functionalities monofunctional, difunctional and polyfunctional silanes, eg (RO) 3 SiNH wherein R is alkyl
- functionalised and unfunctionalised polysilsesquioxanes examples of which are disclosed in the following references:
- Polyethylene vinyl alcohol has been found to be particularly suitable. Modifications of the polymers may be necessary to improve resistance to reactions with various components of the food product or beverage (eg wine).
- the polymer coatings and diffusion layers of the present invention may be used in conjunction with lubricants, such as paraffin or Vaseline, to make the coated cork easier to insert into a bottle and later extract.
- lubricants such as paraffin or Vaseline
- the method of applying the polymer to the substrate will be dependent on the nature of the polymer and of the substrate, and will include such conventional processes as film formation, adsorption from solution, reactive-adhesion to cork, melt polymer application (eg thermof orming, vacuum forming and plasma polymerisation), UV curing and Corona discharge processes.
- the polymers may also be components of multilayer laminate structures.
- the substrate eg cork
- a solution eg ethanol, water or a mixture of ethanol and water
- FIG 1 is the result of Scanning Electrode Microscopy (SEM) of the coating of Example 1.
- FIG 2 is the result of SEM of the coating of Example 2.
- FIGS 3A-D are the results of SEM of the coating of Example 3.
- Corks were spiked with TCA by soaking 100 corks in 1.5 litres of a lOOmg/L solution of TCA in absolute ethanol for 24 hours. The corks were then removed from the solution and allowed to dry in a 40°C oven for 24 hours before being submitted for sensory evaluation to ensure that the corks have TCA odours. These corks were then coated with the coatings described below and sent for sensory evaluation.
- Coated TCA spiked corks were immersed in approximately 150mL of white wine for 24 hours.
- the wine was evaluated for unacceptable odours by a team of experts, being a group of no less than three qualified trained sensory e valuators.
- the samples were given a rating of between 1 and 4.
- a rating 1 indicated a slight odour, rating 2 a moderate odour, rating 3 a strong odour and rating 4 a very strong odour.
- a rating of 2 or less was acceptable.
- the sensory evaluation tests related primarily to TCA odours, which were indicative of likely problems relating to undesirable flavour- and odour- active compounds.
- TCA spiked cork and a non-TCA cork were coated with the coatings described below and subjected to sensory evaluation.
- a solution of 10% Bistrimethoxysilypropylamine in ethanol was stirred while water (adjusted to pH 10 using sodium hydroxide) was added.
- the corks were immediately dipped into the solution and allowed to cure in an oven at 80 C for 30 minutes.
- a bistriethoxysilane (BTSE) solution was prepared by adding ethanol to a 5% BTSE-in-water solution adjusted to a pH of 10 with acetic acid. The solution was allowed to hydrolyse for 48 hours.
- a TCA spiked cork was dipped into this solution and quickly dried with compressed air. Next, the cork was dipped into a 2% amino propyltriethoxysilane-in- water solution, which had been allowed to hydrolyse for 48 hours. The cork was then cured in an 80°C oven for 10 minutes.
- the coating formulation consisted of a mixture of 75mL of polyvinyiacetate emulsion (PVA) and 25mL of polymethylhydrogen siloxane emulsion. 100 corks were placed into a tumbler and 20mL of the coating formulation was distributed casually over the corks. The corks were tumbled, to evenly distribute and dry the coating, for 1 hour at 40 C.
- PVA polyvinyiacetate emulsion
- Corks were dipped into this coating and allowed to cure in an oven at 40 C for 24 hours.
- the polymer was diluted to 25% (v/v) with ethanol and the cork was dipped into this coating and then dried at 40 C for 24 hours.
- Polyethylene vinyl alcohol (EVOH) film (9g) was placed into a reaction vessel and purged with nitrogen for several minutes. Toluene (280mL), isocyanatopropyltriethoxysilane (lOmL) and dibutyltin dilaurate (lmL) were added and the reaction was allowed to proceed under nitrogen at 50 C for 24 hours. The film samples was then washed with tetrahydrofuran (THF) (3xl5mL), tert-butyl alcohol (2xl5mL), toluene (2xl5mL) and dried under vacuum (10 hours). The film was wrapped around the cork, and then sealed with a heat gun.
- THF tetrahydrofuran
- Example 7 Partial co-hydrolysis and condensation of TMOS and EVOH- OC(0)NH(CH 2 ) 3 Si(OEt) 3
- TMOS tetramethoxysilane
- tert-butyl alcohol 86.6mL
- water 12.2mL
- hydrochloric acid 0.2mL
- the reaction was allowed to proceed for 48 hours at room temperature, washed with tert-butyl alcohol (3x5mL), water (3x5mL) and toluene (3xl5mL), and dried under vacuum for 6 hours.
- the film was wrapped around the cork, and then sealed with a heat gun.
- Example 8 Polyethylene / Metallised Polyethylene Terephthalate / Polyethylene Laminate Film
- a polyethylene/ metallised polyethylene terephthalate/ polyethylene laminate film was wrapped around the cork, and then sealed with a heat gun.
- Example 9 Polyethylene / Polyethylene Vinyl Alcohol / Polyethylene Laminate Film
- a polyethylene/ polyethylene vinyl alcohol/ polyethylene laminate film was wrapped around the cork, and then sealed with a heat gun.
- a polyethylene/ nylon/ polyethylene laminate film was wrapped around the cork, and then sealed with a heat gun.
- Example 11 Polyvinyiacetate / Aminosiloxane Emulsion
- the cork was dipped into a solution consisting of 75% Polyvinyiacetate emulsion and 25% Aminosiloxane emulsion. The coating was then cured in an oven at 38 C for 1 hour.
- Example 12 Polyvinylidene Chloride / Polymethylhydrogen Siloxane Emulsion
- the cork was dipped into a solution consisting of 75% Polyvinylidene chloride and 25% polymethylhydrogen siloxane emulsion. The coating was then cured in an oven at 38 C for 1 hour.
- Corks can be rinsed or soaked with hot or cold water, alcohol, or a mixture of both water and alcohol, before the coating is applied. This reduces the occurrence of taint and other unwanted odours by washing away any taint compounds already on the surface of the cork. It is thought that any surface taint could mix with the coating during the coating process and remain on the surface of the coating, thus contributing to, rather than preventing, the taint problem. Accordingly, it is preferable to carry out a washing procedure, eg as in Example A, B, C or D below, prior to coating corks. The corks are then dried, eg in an oven at 40 C for 24 hours, prior to being coated.
- a washing procedure eg as in Example A, B, C or D below
- Corks spiked with lOOmg/L of TCA in absolute ethanol were arranged in a single layer and passed through streams of hot water for 30 seconds and then allowed to dry.
- Corks spiked with lOOmg/L of TCA in absolute ethanol were arranged in a single layer and passed through streams of liquid containing cold water and absolute ethanol and then allowed to dry.
- Corks spiked with lOOmg/L of TCA in absolute ethanol were completely immersed in a solution of hot water for 30 minutes and allowed to dry.
- Corks spiked with lOOmg/L of TCA in absolute ethanol were completely immersed in a solution containing a mixture of cold water and absolute ethanol.
- the simplest application method is dip coating, involving a container filled with the coating formulation into which the substrate (such as a cork) is immersed and then withdrawn.
- a typical dip coating unit consists of a bath, filled with the coating formulation, and a mechanism on which the substrate is mounted for immersion and withdrawal. It is often necessary to circulate and filter the coating to maintain a homogeneous mixture.
- a fixing mechanism must be designed to ensure the proper orientation of the substrate during immersion into and withdrawal from the fluid.
- the fluid is atomised into fine droplets for application to the substrate.
- the size of the droplets formed during atomisation can be controlled by such properties as fluid flow, fluid pressure, air pressure, solution viscosity, and surface tension.
- a number of different nozzle designs are used in industry, such as compressed air spray nozzles, airless spray nozzles, and hot spray systems.
- Slot coating and curtain coating are more appropriate techniques for a continuous operation.
- the methods involve a stationary die, which delivers a layer of coating onto a substrate moving beneath it.
- the difference between the methods is in the way that the coating is transferred from the die to the moving substrate.
- the coating is spread by the slot method when the die slot is close to the substrate; but changing the orientation of the die slot relative to the conveyor and allowing the formulation to cascade is referred to as curtain coating.
- Multiple slots in the die face or converging feed to a single slot can produce multilayer coatings.
- Roll coating is another method used in continuous manufacturing operations primarily for coating films.
- a substrate is fed between two rotating cylinders, while simultaneously directing the coating into the space between the cylinders.
- Formulation viscosity, speed of the substrate, coating flow rate, and distance between the rolls all contribute to coating thickness and uniformity. Although these systems are limited in the types of substrate that can be coated, they can rapidly produce a very uniform product.
- UV light One of the most popular techniques used to initiate cross-linking is irradiation by ultraviolet light. It can be a more rapid process than thermal curing, sometimes taking less than a second to act. Very little heat is generated during the exposure, which can often be carried out at room temperature.
- Electron beam (E-beam) radiation shares the same benefits as UN radiation, without the need for a photoinitiation.
- the exposure forms free radicals that cause the chain reaction.
- Cycle times for Y-ray systems can be longer than for E-beam, at least for conventional polymer matrices, but for curing hydrophilic coatings this does not present a problem.
- Thin polymer films can be deposited onto various substrates through the use of plasma polymerisation.
- a plasma is generated by means of electron excitation, with a gas mixture and an organic monomer.
- These thin films can be between a few hundred angstroms to a micrometre in thickness.
- Cross-linking density is usually greater than in conventionally applied coatings, and thin films exhibiting good adhesion can be laid down on virtually any type of substrate.
- Surface grafting techniques incorporate some of the same general concepts as coating and curing operations but may be more appropriate where exceptionally thin surface layers are desired. Points that distinguish surface grafting from "wet" coating operations are related mainly to the formation of the modified surface layer and the general molecular structures that result.
- a continuous phase is formed by the reactions of the monomeric or polymeric ingredients, and is adhered to the substrate surface through secondary molecular interactions such as hydrogen bonding, London dispersive forces or acid-base interactions. Primary covalent bonding is also possible if the substrate has been pre-treated with molecular groups.
- the monomeric (or polymeric with reactive end groups) components react directly with a polymeric substrate.
- Various forms of radiation such as UV, electron beam, and Y-rays, may be used to cause the formation of peroxide groups on the polymer surface. These are unstable so decompose, and cause initiation of polymerisation in the process.
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- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Details Of Rigid Or Semi-Rigid Containers (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU39492/00A AU3949200A (en) | 1999-04-22 | 2000-04-20 | Treated closures 1 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPP9892 | 1999-04-22 | ||
AUPP9892A AUPP989299A0 (en) | 1999-04-22 | 1999-04-22 | Treated closures 1 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000064647A1 true WO2000064647A1 (fr) | 2000-11-02 |
Family
ID=3814091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AU2000/000365 WO2000064647A1 (fr) | 1999-04-22 | 2000-04-20 | Fermetures traitees |
Country Status (2)
Country | Link |
---|---|
AU (1) | AUPP989299A0 (fr) |
WO (1) | WO2000064647A1 (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6416817B1 (en) * | 2000-03-03 | 2002-07-09 | Dow Corning Sa | Barrier coatings having bis-silanes |
WO2003074379A3 (fr) * | 2002-03-06 | 2003-11-27 | Bacchus Wine Closures Ltd | Bouchons |
WO2004060763A1 (fr) * | 2003-01-07 | 2004-07-22 | Procork Pty Ltd | Procede et appareil permettant d'appliquer un film sur un bouchon de recipient |
US6793972B2 (en) * | 2000-09-12 | 2004-09-21 | The Dow Chemical Company | Gas permeation resistant synthetic cork closure |
AU2002318964B2 (en) * | 2001-07-04 | 2005-05-12 | Procork Pty Ltd | Container stopper |
DE102006016054A1 (de) * | 2006-04-04 | 2007-10-11 | Henkel Kgaa | PU Korkbeschichtung |
WO2013174970A1 (fr) | 2012-05-24 | 2013-11-28 | Henkel Ag & Co. Kgaa | Corps moulé obtenus à partir de granulés et de colles polyuréthane bicomposantes, et contenant des isocyanates aliphatiques |
Citations (12)
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US4254170A (en) * | 1978-02-13 | 1981-03-03 | Rhone-Poulenc Industries | Process for rendering polyester hollow bodies gastight |
EP0039626A1 (fr) * | 1980-05-07 | 1981-11-11 | Toyo Seikan Kaisha Limited | Bouteille en matière plastique et procédé pour sa fabrication |
AU4799585A (en) * | 1984-09-26 | 1986-04-10 | Laporte Chemicals (Australia) Pty. Limited | Treated corks |
EP0341937A2 (fr) * | 1988-05-09 | 1989-11-15 | International Paper Company | Récipient sans fuites et imperméable à l'oxygène |
EP0423511A1 (fr) * | 1989-10-16 | 1991-04-24 | Tetra Laval Holdings & Finance SA | Matériau d'emballage stratifié |
EP0538774A2 (fr) * | 1991-10-22 | 1993-04-28 | Toyo Boseki Kabushiki Kaisha | Composition de polyester pour le revêtement d'un feuille métallique utilisée pour la fabrication de boîtes en deux parties, et feuille revêtue de cette composition |
WO1996028378A1 (fr) * | 1995-03-16 | 1996-09-19 | Dewco Investments Pty. Ltd. | Dispositif de fermeture en liege presentant une couche impermeable aux liquides et resistante pour eviter toute alteration |
US5576068A (en) * | 1995-05-04 | 1996-11-19 | Societe De Transformation Des Elastomers A Usages Medicaux Et Industriels | Method of treating a packaging element, especially for medical or pharmaceutical use; packaging element thus treated |
WO1997001427A1 (fr) * | 1995-06-26 | 1997-01-16 | Valyi Emery I | Recipient pour aliments et boissons en plastique moule et procede correspondant |
WO1997011894A1 (fr) * | 1995-09-28 | 1997-04-03 | Jess Paul Fuller | Bouchon de liege pourvu d'un revetement |
WO1997030122A1 (fr) * | 1996-02-20 | 1997-08-21 | Cellresin Technologies, L.L.C. | Bouteilles pour boissons en polymere rigide dotees d'une resistance amelioree a l'elution de permeants |
DE29912842U1 (de) * | 1999-07-22 | 1999-09-16 | Bleckmann GmbH & Co., 74080 Heilbronn | Flaschenkorken |
-
1999
- 1999-04-22 AU AUPP9892A patent/AUPP989299A0/en not_active Abandoned
-
2000
- 2000-04-20 WO PCT/AU2000/000365 patent/WO2000064647A1/fr active Application Filing
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US4254170A (en) * | 1978-02-13 | 1981-03-03 | Rhone-Poulenc Industries | Process for rendering polyester hollow bodies gastight |
EP0039626A1 (fr) * | 1980-05-07 | 1981-11-11 | Toyo Seikan Kaisha Limited | Bouteille en matière plastique et procédé pour sa fabrication |
AU4799585A (en) * | 1984-09-26 | 1986-04-10 | Laporte Chemicals (Australia) Pty. Limited | Treated corks |
EP0341937A2 (fr) * | 1988-05-09 | 1989-11-15 | International Paper Company | Récipient sans fuites et imperméable à l'oxygène |
EP0423511A1 (fr) * | 1989-10-16 | 1991-04-24 | Tetra Laval Holdings & Finance SA | Matériau d'emballage stratifié |
EP0538774A2 (fr) * | 1991-10-22 | 1993-04-28 | Toyo Boseki Kabushiki Kaisha | Composition de polyester pour le revêtement d'un feuille métallique utilisée pour la fabrication de boîtes en deux parties, et feuille revêtue de cette composition |
WO1996028378A1 (fr) * | 1995-03-16 | 1996-09-19 | Dewco Investments Pty. Ltd. | Dispositif de fermeture en liege presentant une couche impermeable aux liquides et resistante pour eviter toute alteration |
US5576068A (en) * | 1995-05-04 | 1996-11-19 | Societe De Transformation Des Elastomers A Usages Medicaux Et Industriels | Method of treating a packaging element, especially for medical or pharmaceutical use; packaging element thus treated |
WO1997001427A1 (fr) * | 1995-06-26 | 1997-01-16 | Valyi Emery I | Recipient pour aliments et boissons en plastique moule et procede correspondant |
WO1997011894A1 (fr) * | 1995-09-28 | 1997-04-03 | Jess Paul Fuller | Bouchon de liege pourvu d'un revetement |
WO1997030122A1 (fr) * | 1996-02-20 | 1997-08-21 | Cellresin Technologies, L.L.C. | Bouteilles pour boissons en polymere rigide dotees d'une resistance amelioree a l'elution de permeants |
DE29912842U1 (de) * | 1999-07-22 | 1999-09-16 | Bleckmann GmbH & Co., 74080 Heilbronn | Flaschenkorken |
Non-Patent Citations (1)
Title |
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DATABASE WPI Derwent World Patents Index; Class A92, AN 1999-529425/45 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6416817B1 (en) * | 2000-03-03 | 2002-07-09 | Dow Corning Sa | Barrier coatings having bis-silanes |
US6793972B2 (en) * | 2000-09-12 | 2004-09-21 | The Dow Chemical Company | Gas permeation resistant synthetic cork closure |
AU2002318964B2 (en) * | 2001-07-04 | 2005-05-12 | Procork Pty Ltd | Container stopper |
AU2002318964B8 (en) * | 2001-07-04 | 2005-09-29 | Procork Pty Ltd | Container stopper |
WO2003074379A3 (fr) * | 2002-03-06 | 2003-11-27 | Bacchus Wine Closures Ltd | Bouchons |
AU2003209462B2 (en) * | 2002-03-06 | 2009-10-01 | Bacchus Technologies Limited | Stopper |
US7993743B2 (en) | 2002-03-06 | 2011-08-09 | Bacchus Technologies Ltd. | Stoppers comprising a cork substrate and a composite barrier layer comprising reactive hot melt polyurethane adhesive |
WO2004060763A1 (fr) * | 2003-01-07 | 2004-07-22 | Procork Pty Ltd | Procede et appareil permettant d'appliquer un film sur un bouchon de recipient |
DE102006016054A1 (de) * | 2006-04-04 | 2007-10-11 | Henkel Kgaa | PU Korkbeschichtung |
WO2013174970A1 (fr) | 2012-05-24 | 2013-11-28 | Henkel Ag & Co. Kgaa | Corps moulé obtenus à partir de granulés et de colles polyuréthane bicomposantes, et contenant des isocyanates aliphatiques |
Also Published As
Publication number | Publication date |
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AUPP989299A0 (en) | 1999-05-13 |
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