EP1345581A2 - Zinc containing dentifrice of reduced astringency - Google Patents
Zinc containing dentifrice of reduced astringencyInfo
- Publication number
- EP1345581A2 EP1345581A2 EP01992031A EP01992031A EP1345581A2 EP 1345581 A2 EP1345581 A2 EP 1345581A2 EP 01992031 A EP01992031 A EP 01992031A EP 01992031 A EP01992031 A EP 01992031A EP 1345581 A2 EP1345581 A2 EP 1345581A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- zinc
- pyrophosphate
- salt
- weight
- 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.)
- Withdrawn
Links
- 235000019606 astringent taste Nutrition 0.000 title claims abstract description 20
- 239000011701 zinc Substances 0.000 title claims abstract description 16
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 16
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000000551 dentifrice Substances 0.000 title description 18
- 239000000203 mixture Substances 0.000 claims abstract description 50
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims abstract description 20
- 150000003751 zinc Chemical class 0.000 claims abstract description 18
- 229920005646 polycarboxylate Polymers 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 125000000129 anionic group Chemical group 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003906 humectant Substances 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical group [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 claims description 6
- 239000011746 zinc citrate Substances 0.000 claims description 6
- 235000006076 zinc citrate Nutrition 0.000 claims description 6
- 229940068475 zinc citrate Drugs 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 5
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical group [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims description 4
- 235000019818 tetrasodium diphosphate Nutrition 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 2
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 claims 2
- 239000000047 product Substances 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 8
- 229920000388 Polyphosphate Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000001205 polyphosphate Substances 0.000 description 6
- 235000011176 polyphosphates Nutrition 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- -1 Na2P2O7 Chemical class 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000003765 sweetening agent Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003082 abrasive agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229920006318 anionic polymer Polymers 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 235000019629 palatability Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- RPZANUYHRMRTTE-UHFFFAOYSA-N 2,3,4-trimethoxy-6-(methoxymethyl)-5-[3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxyoxane;1-[[3,4,5-tris(2-hydroxybutoxy)-6-[4,5,6-tris(2-hydroxybutoxy)-2-(2-hydroxybutoxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]butan-2-ol Chemical compound COC1C(OC)C(OC)C(COC)OC1OC1C(OC)C(OC)C(OC)OC1COC.CCC(O)COC1C(OCC(O)CC)C(OCC(O)CC)C(COCC(O)CC)OC1OC1C(OCC(O)CC)C(OCC(O)CC)C(OCC(O)CC)OC1COCC(O)CC RPZANUYHRMRTTE-UHFFFAOYSA-N 0.000 description 1
- LFJJOPDNPVFCNZ-UHFFFAOYSA-N 2-[hexadecanoyl(methyl)amino]acetic acid Chemical class CCCCCCCCCCCCCCCC(=O)N(C)CC(O)=O LFJJOPDNPVFCNZ-UHFFFAOYSA-N 0.000 description 1
- NGOZDSMNMIRDFP-UHFFFAOYSA-N 2-[methyl(tetradecanoyl)amino]acetic acid Chemical class CCCCCCCCCCCCCC(=O)N(C)CC(O)=O NGOZDSMNMIRDFP-UHFFFAOYSA-N 0.000 description 1
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
- RFRMMZAKBNXNHE-UHFFFAOYSA-N 6-[4,6-dihydroxy-5-(2-hydroxyethoxy)-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)-5-(2-hydroxypropoxy)oxane-3,4-diol Chemical compound CC(O)COC1C(O)C(O)C(CO)OC1OC1C(O)C(OCCO)C(O)OC1CO RFRMMZAKBNXNHE-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010006326 Breath odour Diseases 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 208000002064 Dental Plaque Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 208000032139 Halitosis Diseases 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch 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
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 1
- 229940043256 calcium pyrophosphate Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940023487 dental product Drugs 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940005740 hexametaphosphate Drugs 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000013588 oral product Substances 0.000 description 1
- 229940023486 oral product Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 1
- 229940099402 potassium metaphosphate Drugs 0.000 description 1
- 235000019828 potassium polyphosphate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical class OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000000606 toothpaste Substances 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
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- VSJRDSLPNMGNFG-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate;trihydrate Chemical compound O.O.O.[Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O VSJRDSLPNMGNFG-UHFFFAOYSA-H 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
- 229940085658 zinc citrate trihydrate Drugs 0.000 description 1
- 229940077935 zinc phosphate Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/24—Phosphorous; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Definitions
- the present invention relates to a dentifrice composition useful for reducing oral malodor and more particularly a low astringent breath freshening oral care product for the treatment of oral malodor containing a combination of zinc and pyrophosphate salts.
- Oral malodor, or halitosis is caused by the putrefactive activity of microorganisms on appropriate substrate components of dental plaque, debris adhering to mucous membranes and salivary cellular elements to produce volatile sulfur compounds primarily hydrogen sulfide, methyl mercaptan and traces of methyl sulfide.
- US 4,138,477 discloses a zinc salt containing oral composition of reduced astringency wherein the composition contains a zinc-polymer complex formed by the reaction of a zinc salt with an anionic polymer containing carboxylic, sulfonic and/or phosphonic acid radicals.
- US 5,000,944 discloses a zinc containing antitartar oral product substantially free of astringency, containing as the essential agent, a zinc/polyphosphate complex having at least about a 50% water solubility, formed by reaction of a zinc salt with a potassium or sodium polyphosphate salt by dissolving a zinc salt in a polyphosphate solution such as pyrophosphate, tripolyphosphate, hexametaphosphate and combinations thereof.
- a zinc/polyphosphate complex having at least about a 50% water solubility, formed by reaction of a zinc salt with a potassium or sodium polyphosphate salt by dissolving a zinc salt in a polyphosphate solution such as pyrophosphate, tripolyphosphate, hexametaphosphate and combinations thereof.
- a drawback to zinc/polyphosphate complex salts is that although astringency is substantially reduced, dentifrices containing zinc and polyphosphate salts have a propensity towards instability, wherein during storage, polycrystalline lumps form, such formation being believed to be caused by the aggregation of crystals of the zinc- polyphosphate complex. These lumps are visible to the naked eye, have a substantial hardness so that the spontaneous formation of these zinc/polyphosphate crystals are highly undesirable and detrimental to consumer acceptance of the dental product. Therefore, there is a need in the art for a means whereby both the stability and astringency characteristics of oral care products containing zinc salts can be improved so that such products will be more acceptable for use by consumers.
- a stable aqueous oral care composition for the treatment of oral malodor having limited astringency comprising an orally acceptable vehicle containing a complex formed from zinc salt, anionic polycarboxylate polymer and a pyrophosphate salt ingredients incorporated in to the oral care composition.
- the presence of the zinc anionic polycarboxylate polymer pyrophosphate complex in the oral care product unexpectedly provides a stable product of substantially reduced astringency having improved palatability when used by the consumer.
- the source of zinc ion used to form the zinc/anionic polycarboxylate polymer/pyrophosphate complex in the oral care composition is generally a zinc salt that is fully or partially soluble in water, including zinc nitrate, zinc sulfate, zinc citrate, zinc chloride, zinc citrate being preferred.
- the zinc salt is generally incorporated in the oral care composition of the present invention at a concentration of about 1 to about 5% by weight and preferably about 1.5 to about 3% by weight.
- Anionic polycarboxylate polymers used to form the zinc/anionic polycarboxylate polymer/pyrophosphate complex are generally employed in the form of their free acids or preferably partially or fully neutralized water soluble alkali metal (e.g., potassium and preferably sodium) or ammonium salts.
- Preferred are 1 :4 to 4:1 copolymers of maleic anhydride or acid with another polmerizable ethylenically unsaturated monomer, preferably methylvinylether/maleic anhydride having a molecular weight (M.W.) of about 30,000 to about 1,800,000 most preferably about 30,000 to about 700,000.
- copolymers examples are available from ISP Corporation under the tradename Gantrez, e.g., AN 139 (M.W. 500,000), AN 119 (M.W. 250,000); S-97 Pharmaceutical Grade (M.W. 700,000), AN 169 (M.W. 1,200,000-1800,000), and AN 179 (M.W. above 1,800,000); wherein the preferred copolymer is S-97 Pharmaceutical Grade (M.W. 700,000).
- Gantrez e.g., AN 139 (M.W. 500,000), AN 119 (M.W. 250,000); S-97 Pharmaceutical Grade (M.W. 700,000), AN 169 (M.W. 1,200,000-1800,000), and AN 179 (M.W. above 1,800,000); wherein the preferred copolymer is S-97 Pharmaceutical Grade (M.W. 700,000).
- the anionic polycarboxylate polymer is employed in amounts effective to form the zinc-polymer-pyrophosphate complex within the oral composition.
- the anionic polycarboxylate polymer is incorporated in the oral care composition from about 0.1% to about 10% by weight, preferably from about 0.2% to about 3.0% by weight.
- Pyrophosphate salts used to prepare the zinc/anionic polymer/pyrophosphate complexes include dialkali or tetraalkali metal pyrophosphate salts such as Na 2 P 2 O 7 ,
- the pyrophosphate salts are included in the oral composition of the present invention at a concentration of about 1 to about 5% by weight and preferably about 0.5 to about 3% by weight.
- the zinc salt anionic polycarboxylate polymer and pyrophosphate salt ingredients are incorporated in the oral care product which includes a vehicle which contains water, humectant, surfactant and a polishing agent.
- the humectant is generally a mixture of humectants, such as glycerol, sorbitol and polyethylene glycol of molecular weight in the range of 200-1000, but other mixtures of humectants and single humectants may also be employed.
- the humectant content is in the range about of 10% to about 80% by weight and preferably about 30 to about 50% by weight.
- the water content is in the range of about 10 to about 25% by weight.
- Inorganic thickeners may be included in the dentifrice component in which potassium salts are included as an ingredient include fumed silicas such as Cabosil available from Cabot Corporation, and thickening silicas including those available from Crosfield Chemicals designated Sorbosil TC-15 or Sylox 15 from W.R. Grace.
- fumed silicas such as Cabosil available from Cabot Corporation
- thickening silicas including those available from Crosfield Chemicals designated Sorbosil TC-15 or Sylox 15 from W.R. Grace.
- Organic thickeners of natural and synthetic gums may be incorporated in the oral care composition of the present invention.
- examples of such thickeners are carrageenan (Irish moss), xanthan gum, sodium carboxymethyl cellulose, starch, polyvinylpyrrolidone, hydroxyethylpropylcellulose,hydroxybutyl methyl cellulose, hydroxypropyl methyl cellulose, and hydroxyethyl cellulose.
- the organic thickener may be incorporated in the compositions of the present invention at a concentration of about 0.25 to about 2% by weight and preferably about 0.5 to about 1% by weight.
- Surfactants may be incorporated in the oral care product of the present invention included as an ingredient to provide foaming properties.
- the surfactant is preferably anionic, suitable examples of which include higher alkyl sulfates such as potassium or sodium lauryl sulfate which is preferred, higher fatty acid monoglyceride monosulfates, such as the salt of the monosulfated monoglyceride of hydrogenated coconut oil fatty acids, alkyl aryl sulfonates such as sodium dodecyl benzene sulfonate, higher fatty sulfoacetates, higher fatty acid esters of 1,2 dihydroxy propane sulfonate, and the substantially saturated higher aliphatic acyl amides of lower aliphatic amino carboxylic acid compounds, such as those having 12 to 16 carbons in the fatty acid, alkyl or acyl radicals, and the like.
- amides are N-lauroyl sarcosine, and the salts of N-lauroyl, N-myristoyl, or N-palmitoyl sarcosine.
- the surfactant is generally present in the oral care compositions of the present invention at a concentration of about 0.5 to about 5.0% by weight.
- Abrasives may be incorporated in the oral composition of the present invention and preferred abrasives are siliceous materials, such as silica.
- a preferred silica is a precipitated amorphous hydrated silica, such as Sorbosil AC-35, marketed by Crosfield Chemicals, or Zeodent 115 and Zeodent 165 from Huber Company but other abrasives may also be employed, including sodium metaphosphate, potassium metaphosphate, tricalcium phosphate, calcium phosphate dihydrate, anhydrous dicalcium phosphate, calcium pyrophosphate, magnesium orthophosphate, calcium carbonate, sodium bicarbonate, alumina trihydrate, aluminum silicate, calcined alumina and bentonite.
- the concentration of abrasive in the oral composition of the present invention will normally be in the range of 5 to about 40% by weight and preferably 10 to 30% by weight.
- ingredients which may be incorporated in the oral care composition of the present invention include pigment, sweetener, flavor and preservative.
- the pigment of choice is titanium dioxide, rutile, and the proportion thereof will normally be in the range of 0.5 to 1.25% by weight, preferably 0.75 to 1 % by weight.
- the sweetener content will normally be that of an artificial or synthetic sweetener and the normal proportion thereof present will be in the range of 0.1 to 1% by weight, preferably 0.3 to 0.5% by weight.
- the flavor content which is preferably of a mixed peppermint/menthol flavor, will usually be in the range of 0.5 to 2% by weight, preferably 0.5 to 1.5% by weight.
- F.D the pigment of choice is titanium dioxide, rutile, and the proportion thereof will normally be in the range of 0.5 to 1.25% by weight, preferably 0.75 to 1 % by weight.
- the sweetener content will normally be that of an artificial or synthetic sweetener and the normal proportion thereof present will be in the range of 0.1 to 1% by weight
- the contents of other components or adjuvants of the potassium salt containing dentifrice will normally not exceed 10% by weight, often will be less than 5% by weight, and can be as low as 0%.
- the zinc salt is added to a mixture of water, humectants and anionic polycarboxylate polymer and dispersed in a conventional mixer until the mixture becomes a slurry which is smooth in appearance.
- the pyrophosphate salt may also be added at this point, preferably predissolved as a water solution.
- Other water soluble ingredients such as fluoride salts and sweeteners such as sodium saccharin may also be added at this point.
- This mixture may be heated to 100-110°F and mixed for 10 to 30 minutes producing a homogeneous gel phase. The mixture is transferred to a vacuum mixer.
- the abrasive is then added and mixed for 10 to 30 minutes at high speed under a vacuum in the range of 5 to 100 millimeter of mercury pressure, preferably 5 to 50 mm Hg, providing a homogenous mixture.
- the surfactant and flavor are then added to the paste which is followed by mixing another 10 to 20 minutes under vacuum of 5 to 50 mm Hg.
- the resultant product is a stable astringent dentifrice of a texture like that of normal toothpastes or gels having a pH in the range of 5 to 8, preferably 6.5 to 7.5, e.g., 7, and of satisfactory flavor.
- the astringency and palatability of the dentifrice was evaluated by a flavorist for attributes such as astringency and taste acceptability as compared to a commercial non- astringent antibacterial dentifrice which did not contain zinc ion and a commercial dentifrice known to be astringent containing 2% by weight zinc citrate.
- the flavorist rated the dentifrice as having minor astringency.
- the dentifrice of the Example was prepared in which the zinc citrate was incorporated in the dentifrice composition together with 1% by weight tetrasodium pyrophosphate and 7% by weight of sodium tripolyphosphate and the anionic polycarboxylate polymer Gantrez S-97 was not included in the dentifrice composition, the composition had low astringency but undesirable crystals formed in the dentifrice within 15 days when stored in plastic tubes at room temperature.
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Abstract
Description
Claims
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73014300A | 2000-12-05 | 2000-12-05 | |
| US730143 | 2000-12-05 | ||
| PCT/US2001/046895 WO2002045678A2 (en) | 2000-12-05 | 2001-12-04 | Zinc containing dentifrice of reduced astringency |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1345581A2 true EP1345581A2 (en) | 2003-09-24 |
Family
ID=24934113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP01992031A Withdrawn EP1345581A2 (en) | 2000-12-05 | 2001-12-04 | Zinc containing dentifrice of reduced astringency |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1345581A2 (en) |
| JP (1) | JP2004517833A (en) |
| KR (1) | KR20030068166A (en) |
| CN (1) | CN1220479C (en) |
| AR (1) | AR031782A1 (en) |
| AU (1) | AU2002232507A1 (en) |
| BR (1) | BR0115949A (en) |
| CA (1) | CA2431002A1 (en) |
| CZ (1) | CZ20031836A3 (en) |
| EC (1) | ECSP034678A (en) |
| HU (1) | HUP0600590A2 (en) |
| MX (1) | MXPA03004922A (en) |
| PL (1) | PL361856A1 (en) |
| RU (1) | RU2259193C2 (en) |
| SK (1) | SK8642003A3 (en) |
| WO (1) | WO2002045678A2 (en) |
| YU (1) | YU44003A (en) |
| ZA (1) | ZA200304561B (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG169990A1 (en) | 2005-12-21 | 2011-04-29 | Colgate Palmolive Co | Improved oral compositions comprising zinc citrate and/or tocopherol agents |
| US8628755B2 (en) | 2007-01-30 | 2014-01-14 | Colgate-Palmolive Company | Dentifrice containing zinc ions and polyphosphate ions |
| CA2753671C (en) * | 2009-04-02 | 2014-11-18 | Colgate-Palmolive Company | Dentifrice composition |
| TWI442937B (en) * | 2009-05-26 | 2014-07-01 | 美國棕欖公司 | Higher loading zinc-containing films |
| CN102596154B (en) | 2009-10-29 | 2014-12-24 | 高露洁-棕榄公司 | Dentifrice comprising stannous fluoride plus zinc citrate and low levels of water |
| TWI554286B (en) * | 2010-01-29 | 2016-10-21 | 美國棕欖公司 | Oral care products for sensitive enamel care (2) |
| SG182316A1 (en) * | 2010-01-29 | 2012-08-30 | Colgate Palmolive Co | Oral care product for sensitive enamel care |
| CN103260704B (en) * | 2010-11-04 | 2016-09-07 | 高露洁-棕榄公司 | Dentifrice composition with reduced astringency |
| MX353686B (en) | 2012-12-18 | 2018-01-24 | Colgate Palmolive Co | Stable metal ion containing compositions. |
| CN106456461B (en) * | 2014-04-30 | 2020-03-06 | 高露洁-棕榄公司 | Oral care compositions containing silica and zinc citrate |
| CN106255487B (en) * | 2014-05-14 | 2020-06-16 | 宝洁公司 | Oral care compositions with improved stability |
| RU2726198C2 (en) | 2015-07-17 | 2020-07-09 | Колгейт-Палмолив Компани | Compositions for oral care |
| MX375425B (en) | 2015-11-13 | 2025-03-06 | Procter & Gamble | Dentifrice compositions with improved fluoride uptake |
| MX383491B (en) * | 2015-11-13 | 2025-03-14 | Procter & Gamble | TOOTHPASTE COMPOSITIONS WITH ANTI-TARTAR AND ANTIBACTERIAL BENEFITS. |
| CN117338605A (en) | 2015-11-13 | 2024-01-05 | 宝洁公司 | Dentifrice composition with dual fluoride source and improved fluoride uptake |
| MX366957B (en) | 2015-11-13 | 2019-07-29 | Procter & Gamble | Dentifrice compositions with improved fluoride stability. |
| CN109152719A (en) * | 2016-05-10 | 2019-01-04 | 高露洁-棕榄公司 | Alginates dentifrice composition and preparation method thereof |
| CN106955244B (en) * | 2017-03-03 | 2019-09-24 | 广州薇美姿实业有限公司 | A kind of composition covering bad mouthfeel and its application in oral care product |
| GB201811065D0 (en) * | 2018-07-05 | 2018-08-22 | GlaxoSmithKline Consumer Healthcare UK IP Ltd | Novel composition |
| BR112022017654A2 (en) | 2020-03-03 | 2022-10-18 | Unilever Ip Holdings B V | AQUEOUS TOOTHPASTE GEL WITHOUT ALCOHOL |
| CN112315827B (en) * | 2020-09-25 | 2023-02-28 | 好维股份有限公司 | Oral care composition and application |
| JP2022100677A (en) * | 2020-12-24 | 2022-07-06 | ライオン株式会社 | Dentifrice composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138477A (en) * | 1976-05-28 | 1979-02-06 | Colgate Palmolive Company | Composition to control mouth odor |
| US5334375A (en) * | 1988-12-29 | 1994-08-02 | Colgate Palmolive Company | Antibacterial antiplaque oral composition |
| US5000944A (en) * | 1989-06-09 | 1991-03-19 | Colgate-Palmolive Company | Zinc-containing oral products with reduced astringency |
| HUT72042A (en) * | 1992-12-18 | 1996-03-28 | Procter & Gamble | Oral compositions containing antiplaque, anticalculus agents |
| US6169118B1 (en) * | 1998-11-12 | 2001-01-02 | Block Drug Company, Inc. | Flavor blend for masking unpleasant taste of zinc compounds |
-
2001
- 2001-12-04 MX MXPA03004922A patent/MXPA03004922A/en not_active Application Discontinuation
- 2001-12-04 HU HU0600590A patent/HUP0600590A2/en unknown
- 2001-12-04 CN CNB01820063XA patent/CN1220479C/en not_active Expired - Fee Related
- 2001-12-04 AU AU2002232507A patent/AU2002232507A1/en not_active Abandoned
- 2001-12-04 RU RU2003120062/15A patent/RU2259193C2/en not_active IP Right Cessation
- 2001-12-04 JP JP2002547464A patent/JP2004517833A/en active Pending
- 2001-12-04 PL PL01361856A patent/PL361856A1/en not_active Application Discontinuation
- 2001-12-04 EP EP01992031A patent/EP1345581A2/en not_active Withdrawn
- 2001-12-04 KR KR10-2003-7007402A patent/KR20030068166A/en not_active Withdrawn
- 2001-12-04 WO PCT/US2001/046895 patent/WO2002045678A2/en not_active Ceased
- 2001-12-04 AR ARP010105634A patent/AR031782A1/en not_active Application Discontinuation
- 2001-12-04 YU YU44003A patent/YU44003A/en unknown
- 2001-12-04 CZ CZ20031836A patent/CZ20031836A3/en unknown
- 2001-12-04 CA CA002431002A patent/CA2431002A1/en not_active Abandoned
- 2001-12-04 SK SK864-2003A patent/SK8642003A3/en unknown
- 2001-12-04 BR BR0115949-6A patent/BR0115949A/en not_active IP Right Cessation
-
2003
- 2003-06-11 ZA ZA200304561A patent/ZA200304561B/en unknown
- 2003-06-27 EC EC2003004678A patent/ECSP034678A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO0245678A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP034678A (en) | 2003-08-29 |
| SK8642003A3 (en) | 2003-12-02 |
| YU44003A (en) | 2006-01-16 |
| CN1479607A (en) | 2004-03-03 |
| HUP0600590A2 (en) | 2007-01-29 |
| AR031782A1 (en) | 2003-10-01 |
| RU2259193C2 (en) | 2005-08-27 |
| ZA200304561B (en) | 2004-08-03 |
| MXPA03004922A (en) | 2003-09-10 |
| JP2004517833A (en) | 2004-06-17 |
| RU2003120062A (en) | 2005-02-10 |
| WO2002045678A3 (en) | 2003-01-16 |
| CA2431002A1 (en) | 2002-06-13 |
| PL361856A1 (en) | 2004-10-04 |
| AU2002232507A1 (en) | 2002-06-18 |
| KR20030068166A (en) | 2003-08-19 |
| WO2002045678A2 (en) | 2002-06-13 |
| BR0115949A (en) | 2003-11-04 |
| CZ20031836A3 (en) | 2003-11-12 |
| CN1220479C (en) | 2005-09-28 |
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