AU771871B2 - Gum base and chewing gum containing edible polyesters - Google Patents
Gum base and chewing gum containing edible polyesters Download PDFInfo
- Publication number
- AU771871B2 AU771871B2 AU23626/00A AU2362600A AU771871B2 AU 771871 B2 AU771871 B2 AU 771871B2 AU 23626/00 A AU23626/00 A AU 23626/00A AU 2362600 A AU2362600 A AU 2362600A AU 771871 B2 AU771871 B2 AU 771871B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- group
- polyester
- gum
- base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920000728 polyester Polymers 0.000 title claims description 110
- 229940112822 chewing gum Drugs 0.000 title claims description 54
- 235000015218 chewing gum Nutrition 0.000 title claims description 54
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 87
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 54
- -1 1,3 butylene diol Chemical class 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 235000011037 adipic acid Nutrition 0.000 claims description 34
- 239000001361 adipic acid Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 32
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 12
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 9
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 235000013355 food flavoring agent Nutrition 0.000 description 8
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
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- 239000000945 filler Substances 0.000 description 5
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000008122 artificial sweetener Substances 0.000 description 4
- 235000021311 artificial sweeteners Nutrition 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
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- 239000003086 colorant Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 150000002314 glycerols Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- 239000001993 wax Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
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- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241001495453 Parthenium argentatum Species 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
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- 241001541238 Vachellia tortilis subsp. raddiana Species 0.000 description 1
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- 229920002494 Zein Polymers 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical class CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
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- 229920003054 adipate polyester Polymers 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 235000019409 alitame Nutrition 0.000 description 1
- 108010009985 alitame Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
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- 150000008064 anhydrides Chemical class 0.000 description 1
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- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000010500 citrus oil Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Chemical class 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 229940099371 diacetylated monoglycerides Drugs 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
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- 239000003480 eluent Substances 0.000 description 1
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- 230000032050 esterification Effects 0.000 description 1
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- UXAYDBNWIBJTRO-UHFFFAOYSA-N ethenyl acetate;ethenyl dodecanoate Chemical compound CC(=O)OC=C.CCCCCCCCCCCC(=O)OC=C UXAYDBNWIBJTRO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
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- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Chemical class C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Chemical class CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical class O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- SELIRUAKCBWGGE-UHFFFAOYSA-N hexadecanoic acid;octadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O SELIRUAKCBWGGE-UHFFFAOYSA-N 0.000 description 1
- BQBUMJXDLQOOAJ-UHFFFAOYSA-N hexanedioic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)CCCCC(O)=O BQBUMJXDLQOOAJ-UHFFFAOYSA-N 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 229920003008 liquid latex Polymers 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 239000001683 mentha spicata herb oil Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
- 235000013856 polydextrose Nutrition 0.000 description 1
- 229940035035 polydextrose Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- MILWSGRFEGYSGM-UHFFFAOYSA-N propane-1,2-diol;propane-1,2,3-triol Chemical compound CC(O)CO.OCC(O)CO MILWSGRFEGYSGM-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Chemical class 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000000892 thaumatin Substances 0.000 description 1
- 235000010436 thaumatin Nutrition 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
- A23G4/08—Chewing gum characterised by the composition containing organic or inorganic compounds of the chewing gum base
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
- A23L33/25—Synthetic polymers, e.g. vinylic or acrylic polymers
- A23L33/26—Polyol polyesters, e.g. sucrose polyesters; Synthetic sugar polymers, e.g. polydextrose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Mycology (AREA)
- Confectionery (AREA)
Description
1 Gum Base And Chewing Gum Containing Edible Polyesters Background of the Invention The present invention relates generally to chewing gum. More specifically the present invention relates to improved formulations for chewing gum and gum bases.
It is of course known to construct chewing gum from a water insoluble gum base and a water soluble portion along with flavor(s). Gum base is designed to be retained in the mouth throughout the chewing period. The water soluble portion and flavors are designed to dissipate during chewing.
Insoluble gum base generally comprises elastomers, resins, fats and oils, softeners, o0 and inorganic fillers. The elastomers can include either synthetic elastomers or natural elastomers. Natural elastomers include natural rubber. Synthetic elastomers include polyisobutylene, isobutylene-isoprene copolymers, styrene-butadiene copolymers, polyvinyl acetate, polyisoprene, polyethylene, vinyl acetate-vinyl laurate copolymers, and S.combinations thereof.
l5 It is also known to use in gum base elastomer plasticizers. Such elastomer plasticizers can include natural rosin esters as well as other elastomer plasticizers.
Additionally, chewing gum base can include filler/texturizers and softener/emulsifiers.
Softeners optimise the chewability and mouth feel of the chewing gum.
Softeners/emulsifiers that are typically used include tallow, hydrogenated tallow, hydrogenated and partially hydrogenated vegetable oils, cocoa butter, glycerol monostearate, glycerol triacetate, lecithin, and combinations thereof.
In addition to a water insoluble gum base portion, a typical chewing gum composition includes a water soluble portion and one or more flavoring agents. The water soluble portion can include bulk sweeteners, high intensity sweeteners, flavoring i 25 agents, softeners, emulsifiers, colors, acidulants, fillers, antioxidants, and other components that provide desirable attributes.
Summary of the Invention The present invention provides improved chewing gum formulations and bases, as well as methods of producing chewing gum and bases. Pursuant to the present invention chewing gum and gum bases that include end-capped edible polyesters are provided. In this regard, traditionally used elastomers and elastomer plasticizers can be replaced with these edible polyesters.
According to a first embodiment of the present invention there is provided a gum base including at least one polyester that is produced through a reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene [R:\LBVV]O3398speci.doc:njc diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
According to a second embodiment of the present invention there is provided a gum base including at least approximately 1% by weight of a polyester that is a product of a reaction of at least one alcohol chosen from the group consisting of trihydroxyl alcohol and dihydroxyl alcohol, and one acid chosen from the group consisting of dicarboxylic acid and tricarboxylic acid, the polyester being end-capped with a monofunctional 0o ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
According to a third embodiment of the present invention there is provided a chewing gum formulation comprising: an insoluble gum base; a water soluble portion; a flavor; and at least 0.1% by weight of a polyester produced by the reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene diol and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid, the polyester being end-capped with a 20 monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
According to a fourth embodiment of the present invention there is provided a method for manufacturing chewing gum comprising the step of adding to a water soluble portion and a flavor an edible polyester produced by the reaction of at least one alcohol 25 chosen from the group consisting of trihydroxyl alcohol and dihydroxyl alcohol and at least one acid chosen from the group consisting of dicarboxylic acid and tricarboxylic acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
According to a fifth embodiment of the present invention there is provided a gum base including at least one polyester that is produced through a reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycerol, and 1,3 butylene diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic aid, and tartaric acid, the polyester being end-capped by a monofunctional ingredient selected from the group consisting of alcohols, acids, [R:\LIBVV]03398speci.doc:njc chlorides, and esters that comprises approximately 22 to about 28% by weight of a resultant polyester.
According to a sixth embodiment of the present invention there is provided a chewing gum whenever manufactured by the method of the fourth embodiment.
The specification describes, in an embodiment, a gum base including at least one edible polyester that is produced through a reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid. The polyester is then end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides and esters.
In an embodiment, the monofunctional ingredient is chosen from the group consisting of long chain or medium chain acyl alcohols, acyl chlorides, fatty acids, fatty alcohols and fatty acid esters.
In an embodiment, the base is wax-free.
15 In an embodiment, the base is non-tacky.
In an embodiment, the base is a bubble gum-type base.
In an embodiment, the edible polyester comprises approximately 1% to about by weight of the base.
In another embodiment, the specification describes a gum base including at least 20 approximately 1% by weight of an edible polyester that is a product of a condensation reaction of at least one alcohol chosen from the group consisting of trihydroxyl alcohol and dihydroxyl alcohol, and at least one acid chosen from the group consisting of dicarboxylic acid and tricarboxylic acid. The polyester is then end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides 25 and esters.
In an embodiment, the monofunctional ingredient is chosen from the group consisting of long or medium chain acyl alcohols, acyl chlorides, fatty acids, fatty alcohols, and fatty acid esters.
In a further embodiment, the specification describes a chewing gum formulation comprising an insoluble gum base, a water soluble portion, a flavor, and at least 0.1% by weight of an edible polyester. The edible polyester is produced by the reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene diol and at least one acid chosen from the group consisting of citric acid, fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid. The polyester is then end- [R:\LIBW]03398speci.doc:njc 3a capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
In an embodiment, the formulation includes a bulk sweetener.
In an embodiment, the formulation includes a high intensity sweetener.
In an embodiment, the formulation includes an elastomer plasticizer.
In an embodiment, the formulation includes an elastomer.
In an embodiment, the chewing gum is sugar free.
In yet a still further embodiment, the specification describes a method for manufacturing chewing gum comprising the step of adding to a water soluble portion and a flavor an edible polyester that is produced by the condensation reaction of at least one alcohol chosen from the group consisting of trihydroxyl alcohol and dihydroxyl alcohol and at least one acid chosen from the group consisting of dicarboxylic acid and tricarboxylic acid. The polyester is then end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
i5 It is an advantage of the present invention to provide an improved gum base.
Still further an advantage of the present invention is to provide an improved chewing gum formulation.
Another advantage of the present invention is to provide an improved method for making chewing gum.
[R:\LIBVV]03398speci.doc:njc WO 00/35297 PCT/US99/29774 Still further an advantage of the present invention is to provide an improved method for making gum base.
Moreover, an advantage of the present invention is that the gum base is biodegradable.
Furthermore, an advantage of the present invention is to replace traditional elastomers or elastomer plasticizers in chewing gum bases with other polymers.
Additional features and advantages of the present invention are described in, and will be apparent from, the detailed description of the presently preferred embodiments.
DETAILED DESCRIPTION OF THE PRESENTLY PREFERRED EMBODIMENTS The present invention provides improved chewing gum formulations and gum base formulations. To this end, the present invention allows for the replacement or substitution for traditional elastomers and elastomer plasticizers with other polymers specifically edible polyesters that are end-capped.
Polyesters are polymers obtained by the esterification of dicarboxylic acid and dihydroxyl alcohol. Ester linkages may be formed at each end of each molecule.
Thus, it is possible to build up a large molecule containing many ester linkages.
For example, one of the most common polyesters in use is polyethylene terephthalate made from ethylene glycol and terephthalic acid. Polyethylene terephthalate was developed as a fiber called Dacron. This polyester can also be used to make a film having unusual strength. Polyethylene terephthalate is currently used to make PET (polyethylene terephthalate) plastic bottles used for soft drinks.
In making polyesters, if a trihydroxyl alcohol such as glycerol is used, possible crosslinking occurs. The resultant resinous materials, glyptols, from glycerol and phthalic acid, find applications as coatings in the lacquer and paint industry.
It is possible to construct polyesters from edible or food grade materials. To this end, the tri or dihydroxyl alcohols glycerol, propylene glycol, and 1,3-butylene diol can be reacted with tri- or dicarboxylic acids such as citric, fumaric, adipic, malic, succinic, and tartaric acids.
WO 00/35297 PCTIUS99/29774 With respect to these alcohols and acids, the reaction of the alcohol and acid form the ester linkages. As the reaction continues extended polyester chains are created by a condensation reaction. An initial study of various polyesters from these materials by the condensation reaction yielded polyesters that had rubbery, plastic or hard, resinlike textures. Because the starting alcohols and acids are food grade materials the resultant product is edible and can be used in food or confectionary products.
Edible polyesters made from glycerol and food grade acids are long chain polymers that continue to grow by a condensation reaction and when the reaction is stopped, free acid and alcohol ends of the polymer are available. The free acid and alcohol ends can be "end-capped" by reacting them with mono-alcohol or mono-acid functional ingredients. Examples of materials that can endcap an edible polyester are: cetyl alcohol (n-hexadecanol, also called palmitic alcohol); palmitic acid; stearic acid; stearic alcohol; stearoyl chloride; other medium and long chain fatty alcohols and acids; cinnamic aldehyde; cellulose; cellulose acetate; modified starch; starch; adipoyl chloride; succinic anhydride; glutaric anhydride and other alphatic chlorides and anhydrides; gum talha; zein; and gelatin.
In a preferred embodiment, medium and long chain fatty acids are used to endcap the edible polyester. In a most preferred embodiment, palmitic acid and palmitic alcohol are used.
To end-cap an edible polyester, generally about 1% to 35% of fatty acids/alcohols is used to obtain the desirable polyester. High levels of fatty acid/alcohols would afford improved texture, more hydrophobicity, and less water extractables. A level of approximately 20 to 28% fatty acid/alcohols is preferred, and most preferably 22 to 28%, to provide the desired edible polyester. Although higher levels may be used to end-cap the polyester, however, too high a level may reduce polyester biodegradability.
The end-capping material may be added any time during the early, middle, or late stages of the reaction.
The end-capped edible polyesters have improved physical properties as base ingredients replacing elastomers, elastomer plasticizers, and resins. These polyesters have improved texture with more rubberiness, improved processability, improved hydrophobicity for extended flavor retention, and better water extractability. By end- WO 00/35297 PCT/US99/29774 capping the edible polyester, the physical properties are improved making them more similar to gum base elastomers, elastomer plasticizers, and resins.
By way of example and not limitation, several polyesters were made using the various food acids and glycerol or propylene glycol. Gram quantities were made in a test tube heated in an oil bath at about 180'-250°C from V 2 hr. to 5 hours to obtain polyesters.
The following polyesters were made: Molar Ratios Glycerin Propvlene Glycol A Adipic Acid 2\1.28 B Adipic Acid 3.54\1.66 C Adipic Acid 1.4\2.03 D Malic Acid 2.0\1.28 E Malic Acid 2\1 F Malic Acid 2\0.5 G Adipic/Malic Acid l\1\1.28 H Adipic/Malic Acid -1.5\1.5\1 I Adipic Acid -2\1 J Adipic Acid 2\2 K Tartaric Acid 2\1 L Fumaric Acid/Citric Acid 1\1\1 M Fumaric Acid 2\1 N Fumaric Acid/Citric Acid 1\1\1 O Adipic Acid 2\1\1** P Adipic Acid Q Adipic Acid -2\.25\1 R Adipic Acid -2\0.4*\2 Low levels of Glycerol added Made with Adipic Acid\Glycerin\Propylene Glycol WO 00/35297 PCT/US99/29774 Products that were formed were viscous liquids to waxy rubbery-like or plastic gels to hard gels. Generally, as the mixtures were heated, moisture was driven off.
Over several hours, liquids turned to gels or if removed from heat became solid gels.
The resultant polyesters were soft to hard plastic and soft to hard rubbery characteristics that had resin like texture. These polyesters appear to be very useful in a gum product. The glycerol adipate polyester was insoluble in water, chloroform, methanol, isopropyl alcohol, 0.1N sodium hydroxide, and concentrated HC1. Other polyesters were not tested for solubility but are believed to be less than 1% soluble in water.
The compatibility of polyesters with other gum base ingredients can be improved by increasing the lipophilicity of the polyester. This can be accomplished by increasing the length of the carbon backbone between the two acids of the dicarboxylic acid molecule.
In this regard, adipic acid has a 4 carbon chain between the two carboxylic acid groups. By increasing the carbon chain between the two groups to a 6, 8, or carbon chain, lipophilicity can be increased. The 6 carbon chain diacid is suberic acid, and 8 carbon chain diacid is sebacic acid, and the 10 carbon chain diacid is dodecanedioic acid.
Other types of naturally occurring diacids may also be used to provide a more lipophilic polyester. Some such diacids include glucaric acid, glutamic acid, glutaric acid, and azelaic acid. Other materials that have at least two carboxylic acids or alcohol groups can also be used as reactants. Such materials with alcohol or hydroxyl groups are sorbitol, mannitol, glycerol monofatty acids and hydrocolloids.
Polyesters can be made by a variety of processes. Besides conventional methods of production, polyesters can be made by a condensation reaction in an extruder, by a condensation reaction in a batch process, or may be made by an enzymatic processes. The process of making the polyester is not limiting.
The polyesters that can be used pursuant to the present invention are not limited to linear polyesters, but can also include polyesters that may be branched or crosslinked. These may be made with tricarboxylic acids or trihyrdoxyl alcohols. The WO 00/35297 PCT/US99/29774 desired polyester may have a broad range of physical properties from thick and syrupy to hard and rubbery with thermoplastic properties.
The examples of polyesters set forth below in Examples A-E were prepared from adipic acid and glycerin or propylene glycol. Both glycerin and propylene glycol were predried by heating in a round bottom flask at 50-60°C under vacuum overnight and stored over a dry helium atmosphere. By way of example, and not limitation, the following examples were made: Example A: In a 2L cylindrical glass reactor equipped with a mechanical stirrer and heating jacket, 800g of dried glycerol was charged. A stream of dry helium was circulated in the reactor and the outlet was connected to a trap maintained in ice-water.
The solution was heated to 100 0 C for 90 min. Then 1900g of adipic was charged into the reactor and the temperature was raised to 150 0 C. Water droplets started condensing. The amount of water condensed is tabulated below as a function of reaction time.
Time of Reaction Amount of water condensed Extent of reaction completed min 100g 21% 150 min 200g 42% 180 min 250g 53% 220 min 310g 66% 240 min 340g 72.6% After 4 hrs the gel point was reached. Two samples were picked out from the reactor at 180 min (Sample and 220 min of reaction (Sample #AA) for analysis. The final product (Sample AAA) was recovered from the reactor. It was observed that the product near the walls was more sticky than the product inside the reactor and was kept in a separate jar. The product inside the reactor was foamy.
FTIR spectroscopy analysis of polymer films of samples A and AA cast on KBr windows from chloroform solutions confirmed the polycondensation products. Also the amount of water condensed from the reaction indicated polyester formation.
WO 00/35297 PCT/US99/29774 Example B In a 3L cylindrical glass reactor equipped with a mechanical stirrer and heating jacket, 700g (9.19 mole) of dried propylene glycol was charged. A stream of dry helium was circulated in the reactor and the outlet was connected to a trap maintained in ice cold water.
The solution was heated to 100 0 C for 90 min. Then 1344.5g (9.19 mole) of adipic acid was charged into the reactor and the temperature was raised to 150 C. Water droplets started condensing. After two hours the reaction temperature was raised to 180°C. In about 3 hrs. 210 ml of water was collected in the trap. The temperature of the reactor was maintained at 180°C and vacuum was applied for about 2 hrs. An additional 120 ml of water was collected in the trap.
An SEC (Size Exclusion Chromatography) analysis (Sample B) of the product indicates the presence of dimers and trimers. The total Mw (Weight Average Molecular Weight) of the product was found to be 2800 and (Weight Average Molecular Weight/Number Average Molecular Weight Polydispersity) Mw/Mn 1.75.
The mechanical stirrer was removed from the reactor and the solution was heated further under vacuum (10 3 mm Hg) at 150°C for 2 hrs; at 180C for 2 hrs; and at 200°C for another 5 hrs. A 15 ml quantity of condensate was collected during this period of heating under a vacuum. An SEC analysis of this product (Sample #BB) shows a Mw of 5500 with Mw/Mn 1.90.
Example C In a 3L cylindrical glass reactor equipped with a mechanical stirrer and heating jacket, 700g (9.19 mole) of dried propylene glycol was charged. A stream of dry helium was circulated in the reactor and the outlet was connected to a trap maintained in ice cold waters.
The solution was heated to 70 0 C for 30 min. Then 1344.5g (9.19 mole) of adipic acid was charged into the reactor and the temperature was raised to 100 0 C. Water droplets started condensing. After one hour 5ml of HCI (0.5 mole%) was added as a catalyst and the reaction temperature was raised to 150°C. In about 1 hr. 100 ml of water was collected in the trap. The pH of the collected water was around 4. The temperature of the reactor was raised to 180 0 C and around 145 ml of water was collected in the trap.
WO 00/35297 PCT/US99/29774 An SEC analysis (Sample C) indicates the presence of dimers and trimers.
The total Mw of the product was 1700 and Mw/Mn 2.43.
The mechanical stirrer was removed from the reactor. 2.5 ml (0.25 mole%) of HCl was added and the solution was heated further under vacuum (10- 3 mm Hg) at 220'C for 4 hrs. A 25 ml quantity of condensate was collected during this period of heating under vacuum. An SEC analysis of this product (Sample #CC) shows the Mw to be 3700 with Mw/Mn 2.47.
As in Example B, size exclusion chromatography (SEC) was carried out on a Varian liquid chromatograph equipped with a refractive detector. Three GPC columns from Supelco were used with THF as the eluent. The columns were calibrated with monodisperse polystyrene standards. The molecular weights and the polydispersity indice were calculated.
Example D In a 3L cylindrical glass reactor equipped with a mechanical stirrer and heating jacket, 313 g (4.11 mole) of dried propylene glycol and 252 g (2.74 mole) of glycerol were charged. A stream of dry helium was circulated in the reactor and the outlet was connected to a trap maintained in ice cold water.
The solution was heated to 75'C for an hour. Then 1200 g (8.22 mole) of adipic acid was charged into the reactor and the temperature of the reactor was kept at 75°C for 2 hours. The temperature was raised to 180'C and water droplets started condensing. After 2 hours, 140 ml of water was collected in the trap. The temperature of the reactor was increased to 220 C and around 90 ml of water was collected in another 2 hrs. Vacuum was applied for about 1 hr at 220 0
C.
The solution became viscous and turned into a gel in about 1 hr. An additional 30 ml of water was collected in the trap. The final product (Sample D) was soft, sticky and difficult to remove from the reactor.
Example E In a 3L cylindrical glass reactor equipped with a mechanical stirrer and heating jacket, 468 g (6.15 mole) of dried propylene glycol and 252 g (2.74 mole) of glycerol were charged. A stream of dry helium was circulated in the reactor and the outlet was connected to a trap maintained in ice cold water.
WO 00/35297 PCTIUS99/29774 The solution was heated to 75'C for an hour. Then 1500 g (10.26 mole) of adipic acid was charged into the reactor and the temperature was kept at 75 C for 2 hrs.
The temperature was raised to 180 0 C and water droplets started condensing. After 2 hrs.
140 ml of water was collected in the trap. The temperature of the reactor was increased to 220 0 C and around 100 ml of water was collected in another 2 hrs. Vacuum was applied for about 1 hr at 220 0
C.
The solution became viscous and a sample was collected after 30 min.
(Sample EE). It was fluid-like. The vacuum was applied for another 30 min. upon which the solution turned into a gel. An additional 70 ml of water was collected in the trap.
The reactor was allowed to cool and final product was recovered. The product (Sample E) was soft and sticky.
Samples D, E, EE were cross linked and would not dissolve in THF and therefore were not analyzed by SEC.
In order to determine the amount of initial material remaining a water washing of Example E was done. Using a Brabender Plasticorder with a 120ml Sigma mixer bowl and blade, 75.8 g of Example E was mixed with 20 ml of deionized water for 16 minutes. After some swelling another 20 ml of water was added and mixed 16 minutes. Then the water extract was removed and more water added. This was repeated more times and the extracts analyzed for solids content. A total of 1.7% of Example E was extracted indicating very little material remained in the polyester. Polyester examples D E were soaked in deionized water at room temperature for about 1 week.
The polyesters were removed from the water and dried in a vacuum oven overnight at to By way of example, and not limitation, examples of end-capped polyesters will now be given.
Example F A reaction mixture of 22.6% palmitic acid, 51.6% adipic acid, and 25.8% glycerol by weight can be prepared as described above. This mixture consists of approximately equimolar amounts of acid and hydroxyl groups.
Briefly the process proceeded using a total mixture of 1600 grams and was as follows: Add 413 grams of dry glycerol to the reaction vessel and heat to 100 0 C. Add -11- WO 00/35297 PCT/US99/29774 825 grams of adipic acid and 362 grams of palmitic acid to the reaction vessel and heat to about 150 0 C and acid continue heating as water starts condensing and continues to condense until the reaction mixture reaches gelation. The batch is considered gelled when it begins to climb the agitator shaft.
At the gelation point for the polyester, tests have shown that approximately of its acid and hydroxyl groups have reacted. This leaves about 30% of the acid and hydroxyl groups non-reacted. A polymer gel has reached its gelatin point where it is a solid matrix and can no longer melt; it can be softened, but cannot melt. For use in gum base it is desirable to have a gelled polyester in order to reduce water extractable materials.
Example G A quantity of polyester can be prepared by mixing 15% hexadecanol (also called cetyl alcohol or palmitic alcohol), 56.6% acidic acid, and 28.4% glycerol by weight and can be prepared as previously described.
Example H A quantity of polyester can be prepared by mixing 11.6% palmitic acid, 11.0% hexadecanol, 51.6% adipic acid, and 25.8% glycerol by weight. Palmitic acid may be added with adipic acid, and hexadecanol near the end of the batch. Process the same as previously described.
The following gum bases were made from the 2 washed polyesters set forth above using a Haake Rheocord Rheometer and Sigma mixer.
Base Example 1 A 50.0 gram quantity of polyester of Example D was placed in a Haake Rheocord with a Sigma blade mixer. Added to this was 20.0 grams of calcium carbonate and blended for 15 minutes at 115 C.
Base Example 2 A 45.0 gram quantity of base of Example 1 above was added to the Haake Rheocord and blended at 115 °C with 20.0 grams of medium molecular weight PVAc for min.
-12- WO 00/35297 PCT/US99/29774 Base Example 3 A 50.2 gram quantity of polyester of Example E was placed in the Haake Rheocord with the sigma mixer blade. Added to this was 30.0 grams of calcium carbonate and blended at 115 °C for 20 minutes.
Base Example 4 A 40.8 gram quantity of base of Example 3 was placed in the Haake Rheocord and blended at 115 C with 10.0 grams of low molecular weight PVAc for minutes.
Gum Examples 5. 6. and 7 The following gums were made from bases made above in a Brabender Plasticorder at 37 C.
Ex 5 Ex6 Ex 7 Base Examples Ex 1 Ex 2 Ex 4 Base, grams 18 18 18 Sugar, grams 41 41 41 45B6 Corn Syrup, grams 11 11 11 Peppt. Flavor, grams 0.7 0.7 0.7 Total 70.7 70.7 70.7 Gum evaluation showed Example 5 with polyester and calcium carbonate had a good initial texture but became very soft and tacky in the late chew texture. Example 6 had a good initial texture as well as a good texture character throughout and was slightly tacky. Example 7 had a good initial texture, but became slightly soft and slightly tacky late.
The polyesters made here were not readily compatible with other base ingredients such as elastomers, elastomer plasticizers, waxes, and fats. By using a 2monoglyceride as the starting diol instead of glycerin or propylene glycol, it is believed that more compatible polyesters can be developed and used with other gum base ingredients.
It was concluded that a quality chewing gum base and gum product can be made from polyesters from adipic acid and glycerol and/or propylene glycol.
WO 00/35297 PCT/US99/29774 The previous Examples F, G, and H of polyesters were made using the following procedure: Procedure The reactants are added to a 2-liter reaction flask having a heating jacket and equipped with a stirrer, a nitrogen inlet, a nitrogen/vacuum outlet with a trap, and a thermocouple. The reactants are added to the reaction vessel in the desired molar ratios of alcohol and acid groups (usually stoichiometrically equivalent).
The reaction vessel is purged with nitrogen and heated to 150 0 C to ensure melting of both reactants. After the reactants are melted, the mixture is stirred with a mechanical stirrer. The mixture is allowed to react for 2-3 hours.
Water is then collected in the condenser and measured to determine the extent of the reaction. When water elution slows (usually about an hour), the nitrogen purge is discontinued and the system is run under vacuum. When water elution slowed again (about 1 hour), the temperature is raised to 180 0 C. After the polyester forms a viscous gel (about 70% reaction completion) and begins to climb the agitator shaft that stops the mixer (usually about 0.5 to 1 hour), the heat is removed. The polyester is then removed and allowed to cool.
Pursuant to the present invention, the polyesters can be used in base formulations and/or chewing gum formulations. In this regard, the polyesters can be used as elastomers and/or elastomer plasticizers. As part of a gum base, the edible polyesters can comprise approximately 1 to about 80% by weight of the gum base. As part of the chewing gum, the edible polyesters can comprise approximately 0.1 to about 70% by weight of the chewing gum.
The polyesters can be used in a variety of different chewing gum and base formulations.
As previously noted, chewing gum generally consists of a water insoluble gum base, a water soluble portion, and flavors.
The insoluble gum base generally comprises elastomers, resins, fats and oils, softeners, and inorganic fillers. The gum base may or may not include wax. The insoluble gum base can constitute approximately 5 to about 95 percent, by weight, of the chewing gum, more commonly, the gum base comprises 10 to about 50 percent of the WO 00/35297 PCT/US99/29774 gum, and in some preferred embodiments, 20 to about 35 percent, by weight, of the chewing gum.
In an embodiment, the chewing gum base of the present invention contains about 1% to about 80% weight percent food grade polyester, about 20 to about 60 weight percent synthetic elastomer, 0 to about 30 weight percent natural elastomer, about 5 to about 55 weight percent elastomer plasticizer, about 4 to about 35 weight percent filler, about 5 to about 35 weight percent softener, and optional minor amounts (about one percent or less) of miscellaneous ingredients such as colorants, antioxidants, etc.
Synthetic elastomers may include, but are not limited to, polyisobutylene with a GPC weight average molecular weight of about 10,000 to about 95,000, isobutyleneisoprene copolymer (butyl elastomer), styrene-butadiene copolymers having styrenebutadiene ratios of about 1:3 to about 3:1, polyvinyl acetate having a GPC weight average molecular weight of about 2,000 to about 90,000, polyisoprene, polyethylene, vinyl acetate-vinyl laurate copolymer having vinyl laurate content of about 5 to about percent by weight of the copolymer, and combinations thereof.
Preferred ranges are, for polyisobutylene, 50,000 to 80,000 GPC weight average molecular weight, for styrene-butadiene, 1:1 to 1:3 bound styrene-butadiene, for polyvinyl acetate, 10,000 to 65,000 GPC weight average molecular weight with the higher molecular weight polyvinyl acetates typically used in bubble gum base, and for vinyl acetate-vinyl laurate, vinyl laurate content of 10-45 percent.
If used, natural elastomers may include natural rubber such as smoked or liquid latex and guayule as well as natural gums such as jelutong, lechi caspi, perillo, sorva, massaranduba balata, massaranduba chocolate, nispero, rosindinha, chicle, gutta hang kang, and combinations thereof. The preferred synthetic elastomer and natural elastomer concentrations vary depending on whether the chewing gum in which the base is used is adhesive or conventional, bubble gum or regular gum, as discussed below.
Preferred natural elastomers include jelutong, chicle, sorva and massaranduba balata.
If used, elastomer plasticizers may include, but are not limited to, natural rosin esters, often called estergums, such as glycerol esters of partially hydrogenated rosin, glycerol esters polymerized rosin, glycerol esters of partially dimerized rosin, WO 00/35297 PCTIUS99/29774 glycerol esters of rosin, pentaerythritol esters of partially hydrogenated rosin, methyl and partially hydrogenated methyl esters of rosin, pentaerythritol esters of rosin; synthetics such as terpene resins derived from alpha-pinene, beta-pinene, and/or d-limonene; and any suitable combinations of the foregoing. the preferred elastomer plasticizers will also vary depending on the specific application, and on the type of elastomer which is used.
Fillers/texturizers may include magnesium and calcium carbonate, ground limestone, silicate types such as magnesium and aluminum silicate, clay, alumina, talc, titanium oxide, mono-, di- and tri-calcium phosphate, cellulose polymers, such as wood, and combinations thereof.
Softeners/emulsifiers may include tallow, hydrogenated tallow, hydrogenated and partially hydrogenated vegetable oils, cocoa butter, glycerol monostearate, glycerol triacetate, lecithin, mono-, di- and triglycerides, acetylated monoglycerides, fatty acids stearic, palmitic, oleic and linoleic acids), and combinations thereof.
Colorants and whiteners may include FD&C-type dyes and lakes, fruit and vegetable extracts, titanium dioxide, and combinations thereof.
The base may or may not include wax. An example of a wax-free gum base is disclosed in U.S. Patent No. 5,286,500, the disclosure of which is incorporated herein by reference.
In addition to a water insoluble gum base portion, a typical chewing gum composition includes a water soluble bulk portion and one or more flavoring agents. The water soluble portion can include bulk sweeteners, high intensity sweeteners, flavoring agents, softeners, emulsifiers, colors, acidulants, fillers, antioxidants, and other components that provide desired attributes.
The softeners, which are also known as plasticizers and plasticizing agents, generally constitute between approximately 0.5 to about 15% by weight of the chewing gum. The softeners may include glycerin, lecithin, and combinations thereof. Aqueous sweetener solutions such as those containing sorbitol, hydrogenated starch hydrolysates, corn syrup and combinations thereof, may also be used as softeners and binding agents in chewing gum.
WO 00/35297 PCT/US99/29774 Bulk sweeteners include both sugar and sugarless components. Bulk sweeteners typically constitute 5 to about 95% by weight of the chewing gum, more typically, 20 to 80% by weight, and more commonly, 30 to 60% by weight of the gum.
Sugar sweeteners generally include saccharide-containing components commonly known in the chewing gum art, including, but not limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, galactose, corn syrup solids, and the like, alone or in combination.
Sorbitol can be used as a sugarless sweetener. Additionally, sugarless sweeteners can include, but are not limited to, other sugar alcohols such as mannitol, hydrogenated isomoltulose (palatinit), xylitol, hydrogenated starch hydrolysates, maltitol, lactitol and the like, alone or in combination.
High intensity artificial sweeteners can also be used in combination with the above. Preferred sweeteners include, but are not limited to sucralose, aspartame, salts of acesulfame, alitame, saccharin and its salts, cyclamic acid and its salts, glycyrrhizin, dihydrochalcones, thaumatin, monellin, and the like, alone or in combination. In order to provide longer lasting sweetness and flavor perception, it may be desirable to encapsulate or otherwise control the release of at least a portion of the artificial sweetener. Such techniques as wet granulation, wax granulation, spray drying, spray chilling, fluid bed coating, coacervation, and fiber extension may be used to achieve the desired release characteristics.
Usage level of the artificial sweetener will vary greatly and will depend on such factors as potency of the sweetener, rate of release, desired sweetness of the product, level and type of flavor used and cost considerations. Thus, the active level of artificial sweetener may vary from 0.02 to about When carriers used for encapsulation are included, the usage level of the encapsulated sweetener will be proportionately higher.
Combinations of sugar and/or sugarless sweeteners may be used in chewing gum. Additionally, the softener may also provide additional sweetness such as with aqueous sugar or alditol solutions.
If a low calorie gum is desired, a low caloric bulking agent can be used.
Example of low caloric bulking agents include: polydextrose; Raftilose, Raftilin; Fructooligosaccharides (NutraFlora); Palatinose oligosaccharide; Guar Gum Hydrolysate WO 00/35297 PCT/US99/29774 (Sun Fiber); or indigestible dextrin (Fibersol). However, other low calorie bulking agents can be used.
A variety of flavoring agents can be used. The flavor can be used in amounts of approximately 0.1 to about 15 weight percent of the gum, and preferably, about 0.2 to about Flavoring agents may include essential oils, synthetic flavors or mixtures thereof including, but not limited to, oils derived from plants and fruits such as citrus oils, fruit essences, peppermint oil, spearmint oil, other mint oils, clove oil, oil of wintergreen, anise and the like. Artificial flavoring agents and components may also be used. Natural and artificial flavoring agents may be combined in any sensorially acceptable fashion.
The present invention, it is believed, can be used with a variety of processes for manufacturing chewing gum.
Chewing gum is generally manufactured by sequentially adding the various chewing gum ingredients to commercially available mixers known in the art. After the ingredients have been thoroughly mixed, the chewing gum mass is discharged from the mixer and shaped into the desired form, such as by rolling into sheets and cutting into sticks, extruding into chunks, or casting into pellets.
Generally, the ingredients are mixed by first melting the gum base and adding it to the running mixer. The gum base may alternatively be melted in the mixer. Color and emulsifiers can be added at this time.
A chewing gum softener such as glycerin can be added next along with part of the bulk portion. Further parts of the bulk portion may then be added to the mixer.
Flavoring agents are typically added with the final part of the bulk portion. The entire mixing process typically takes from five to fifteen minutes, although longer mixing times are sometimes required.
It should be understood that various changes and modifications to the presently preferred embodiments described herein will be apparent to those skilled in the art. Such changes and modifications can be made without departing from the spirit and scope of the present invention and without diminishing its attendant advantages. It is therefore intended that such changes and modifications be covered by the appended claims.
Claims (26)
1. A gum base including at least one polyester that is produced through a reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
2. The gum base of Claim 1 wherein the monofunctional ingredient is selected from the group consisting of long or medium chain acyl alcohols, acyl chlorides, fatty acids, fatty alcohols, and fatty acid esters.
3. The gum base of Claim 1 wherein the base is wax-free.
4. The gum base of Claim 1 wherein the base is non-tacky. The gum base of Claim 1 wherein the base is a bubble gum-type base.
6. The gum base of Claim 1 wherein the polyester comprises approximately 1% to about 80% by weight of the base.
7. The gum base of Claim 1 including at least one elastomer.
8. The gum base of Claim 1 wherein the polyester is end-capped with palmitic acid.
9. The gum base of Claim 1 wherein the monofunctional ingredient comprises approximately 20 to about 28% of the polyester. A gum base including at least approximately 1% by weight of a polyester that is a product of a reaction of at least one alcohol chosen from the group consisting oftrihyrdoxyl alcohol and dihydroxyl alcohol, and one acid chosen from the group consisting of dicarboxylic acid and tricarboxylic acid, the polyester being end- capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
11. The gum base of Claim 10 wherein the monofunctional ingredient is selected from the group consisting of an alcohol or acid selected from the group consisting of long or medium chain acyl alcohols, acyl chlorides, fatty acids, fatty alcohols, and fatty acid esters.
12. The gum base of Claim 10 wherein the base is wax-free. -19- WO 00/35297 PCT[US99/29774
13. The gum base of Claim 10 wherein the base is non-tacky.
14. The gum base of Claim 10 wherein the base is a bubble gum-type base. The gum base of Claim 10 including at least one elastomer.
16. A chewing gum formulation comprising: an insoluble gum base; a water soluble portion; a flavor; and at least 0.1% by weight of a polyester produced by the reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene diol and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
17. The chewing gum of Claim 16 wherein the monofunctional group is selected from the group consisting of an alcohol or acid selected from the group consisting of long or medium chain acyl alcohols, acyl chlorides, fatty acids, fatty alcohols, and fatty acid esters.
18. The chewing gum formulation of Claim 16 wherein the formulation includes a bulk sweetener.
19. The chewing gum formulation of Claim 16 wherein the formulation includes a high intensity sweetener. The chewing gum formulation of Claim 16 wherein the formulation includes an elastomer plasticizer.
21. The chewing gum formulation of Claim 16 wherein the formulation includes an elastomer.
22. The chewing gum of Claim 16 wherein the chewing gum is sugar free.
23. A method for manufacturing chewing gum comprising the step of adding to a water soluble portion and a flavor an edible polyester produced by the reaction of at least one alcohol chosen from the group consisting of trihydroxyl alcohol and dihydroxyl alcohol and at least one acid chosen from the group consisting of 21 dicarboxylic acid and tricarboxylic acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters.
24. A gum base including at least one polyester that is produced through a reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycerol, and 1,3 butylene diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic aid, and tartaric acid, the polyester being end-capped by a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters that comprises approximately 22 to about 28% by io weight of a resultant polyester. The gum base of claim 24 wherein the monofunctional acid is a fatty acid.
26. The gum base of claim 24 wherein the monofunctional acid is chosen from the group consisting of palmitic acid and palmitic alcohol.
27. A gum including at least one polyester that is produced through a reaction of 15 at least one alcohol chosen from the group consisting of glycerol, propylene glycol, and 1,3 butylene diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic acid, and tartaric acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, chlorides, and esters, substantially as herein described with reference to the examples. 20 28. A gum base including at least approximately 1% by weight of a polyester that is a product of a reaction of at least one alcohol chosen from the group consisting of trihydroxyl alcohol and dihydroxyl alcohol, and one acid chosen from the group 0* consisting of dicarboxylic acid and tricarboxylic acid, the polyester being end-capped with a monofunctional ingredient selected from the group consisting of alcohols, acids, 25 chlorides, and esters, substantially as herein described with reference to the examples.
29. A chewing gum formulation substantially as herein described with reference to the examples. A method for manufacturing a chewing gum comprising the step of adding to a water soluble portion and a flavour an edible polyester, which polyester is substantially as herein described with reference to the examples.
31. A gum base including at least one polyester that is produced through a reaction of at least one alcohol chosen from the group consisting of glycerol, propylene glycerol, and 1,3 butylene diol, and at least one acid chosen from the group consisting of fumaric acid, adipic acid, malic acid, succinic aid, and tartaric acid, the polyester being end-capped by a monofunctional ingredient selected from the group consisting of [R:\LIBVV]03398spcci.doc:njc 4 22 alcohols, acids, chlorides, and esters that comprises approximately 22 to about 28% by weight of a resultant polyester, substantially as herein described with reference to the examples.
32. A chewing gum whenever manufactured by the method of claim 23 or Dated 10 February, 2004 Win. Wrigley Jr. Company Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON 0O S OSOS 0S 0 0S S. S OS 5 S S S
555. S. 55 5 0 0 0 S. S 5* S. 55.5 @0.0 5.5. S 0055 00 S 0@ OS SOS. 00 S S S S S SO S *5e50* S S [KALIBVV]03398speci.doc:njc
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/213672 | 1998-12-17 | ||
| US09/213,672 US6013287A (en) | 1996-10-22 | 1998-12-17 | Gum base and chewing gum containing edible polyesters |
| PCT/US1999/029774 WO2000035297A1 (en) | 1998-12-17 | 1999-12-15 | Gum base and chewing gum containing edible polyesters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2362600A AU2362600A (en) | 2000-07-03 |
| AU771871B2 true AU771871B2 (en) | 2004-04-01 |
Family
ID=22796042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU23626/00A Ceased AU771871B2 (en) | 1998-12-17 | 1999-12-15 | Gum base and chewing gum containing edible polyesters |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1139775A4 (en) |
| AU (1) | AU771871B2 (en) |
| CA (1) | CA2356935C (en) |
| WO (1) | WO2000035297A1 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002076227A1 (en) | 2001-03-23 | 2002-10-03 | Gumlink A/S | Coated degradable chewing gum with improved shelf life and process for preparing same |
| US7722894B2 (en) | 2001-10-22 | 2010-05-25 | Massachusetts Institute Of Technology | Biodegradable polymer |
| JP2005516091A (en) * | 2001-10-22 | 2005-06-02 | マサチューセッツ インスティテュート オブ テクノロジー | Biodegradable polymer |
| AU2002342578B2 (en) | 2002-09-24 | 2008-05-15 | Gumlink A/S | Biodegradable chewing gum comprising at least one high molecular weight biodegradable polymer |
| MXPA05002961A (en) * | 2002-09-24 | 2005-06-03 | Gumlink As | Chewing gum comprising at least two different biodegradable polymers. |
| WO2007038919A1 (en) * | 2005-10-03 | 2007-04-12 | Cadbury Schweppes Plc | Chewing gum having modified release |
| EP1973493A2 (en) | 2006-01-12 | 2008-10-01 | Massachusetts Institute of Technology | Biodegradable elastomers |
| US8912304B2 (en) | 2007-05-17 | 2014-12-16 | Massachusetts Institute Of Technology | Polyol-based polymers |
| NO3030597T3 (en) * | 2013-08-09 | 2018-02-10 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122057A (en) * | 1974-09-03 | 1978-10-24 | Emery Industries, Inc. | Mixed-terminated polyester plasticizers |
| US4278785A (en) * | 1979-06-04 | 1981-07-14 | Hooker Chemicals & Plastics Corp. | Polyester composition, process therefor and molded articles therefrom |
| JPS5967248A (en) * | 1982-10-08 | 1984-04-16 | Daicel Chem Ind Ltd | Polyester compound |
| US4525363A (en) * | 1983-06-29 | 1985-06-25 | Nabisco Brands, Inc. | Single compatibilizing agents for elastomer-resin combination gum base |
| KR920702928A (en) * | 1989-11-09 | 1992-12-17 | 원본미기재 | Oral-delivery composition to which flavor is added, and preparation method thereof |
| US5137743A (en) * | 1990-09-07 | 1992-08-11 | Opta Food Ingredients, Inc. | Foods having an oil phase thickened with an oil soluble polyester |
| US5118783A (en) * | 1990-09-12 | 1992-06-02 | Reichhold Chemicals, Inc. | Chain-stopped unsaturated polyester resins |
| DE4034334A1 (en) * | 1990-10-29 | 1992-04-30 | Basf Ag | USE OF WINE ACID CONCENTRATED POLYESTERS AS A DETERGENT ADDITIVE, METHOD OF PREPARING POLYESTER AND POLYESTER FROM WINE ACIDS AND TETRACARBONE ACIDS |
| US5480962A (en) * | 1993-07-22 | 1996-01-02 | Eastman Chemical Company | Copolyesters having repeat units derived from succinic acid |
| NL9401703A (en) * | 1994-10-14 | 1996-05-01 | Rijksuniversiteit | Chewing gum. |
-
1999
- 1999-12-15 EP EP99967326A patent/EP1139775A4/en not_active Withdrawn
- 1999-12-15 CA CA002356935A patent/CA2356935C/en not_active Expired - Fee Related
- 1999-12-15 AU AU23626/00A patent/AU771871B2/en not_active Ceased
- 1999-12-15 WO PCT/US1999/029774 patent/WO2000035297A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1139775A1 (en) | 2001-10-10 |
| CA2356935C (en) | 2005-03-29 |
| CA2356935A1 (en) | 2000-06-22 |
| AU2362600A (en) | 2000-07-03 |
| EP1139775A4 (en) | 2005-01-05 |
| WO2000035297A1 (en) | 2000-06-22 |
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