WO2000059461A1 - Oral composition with an improved teeth whitening effect - Google Patents
Oral composition with an improved teeth whitening effect Download PDFInfo
- Publication number
- WO2000059461A1 WO2000059461A1 PCT/EP2000/002858 EP0002858W WO0059461A1 WO 2000059461 A1 WO2000059461 A1 WO 2000059461A1 EP 0002858 W EP0002858 W EP 0002858W WO 0059461 A1 WO0059461 A1 WO 0059461A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- pyridin
- oral care
- peroxy compound
- catalyst
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 230000002087 whitening effect Effects 0.000 title claims abstract description 11
- -1 peroxy compound Chemical class 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 239000003446 ligand Substances 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002506 iron compounds Chemical class 0.000 claims abstract description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims abstract description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- 238000009472 formulation Methods 0.000 claims description 14
- 150000004965 peroxy acids Chemical class 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000012459 cleaning agent Substances 0.000 claims description 4
- 230000001680 brushing effect Effects 0.000 claims description 3
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007844 bleaching agent Substances 0.000 description 16
- 239000002243 precursor Substances 0.000 description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 11
- 150000003839 salts Chemical group 0.000 description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- 150000002148 esters Chemical group 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 238000004061 bleaching Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- IZWKOTBNIORNES-UHFFFAOYSA-N 1,1-dipyridin-2-yl-n,n-bis(pyridin-2-ylmethyl)ethanamine Chemical compound C=1C=CC=NC=1C(C=1N=CC=CC=1)(C)N(CC=1N=CC=CC=1)CC1=CC=CC=N1 IZWKOTBNIORNES-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
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- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 description 1
- RMKNCYHVESPYFD-UHFFFAOYSA-N decan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCC[NH3+] RMKNCYHVESPYFD-UHFFFAOYSA-N 0.000 description 1
- UNWDCFHEVIWFCW-UHFFFAOYSA-N decanediperoxoic acid Chemical compound OOC(=O)CCCCCCCCC(=O)OO UNWDCFHEVIWFCW-UHFFFAOYSA-N 0.000 description 1
- 239000003975 dentin desensitizing agent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- TVQLLNFANZSCGY-UHFFFAOYSA-N disodium;dioxido(oxo)tin Chemical compound [Na+].[Na+].[O-][Sn]([O-])=O TVQLLNFANZSCGY-UHFFFAOYSA-N 0.000 description 1
- BRDYCNFHFWUBCZ-UHFFFAOYSA-N dodecaneperoxoic acid Chemical compound CCCCCCCCCCCC(=O)OO BRDYCNFHFWUBCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960004867 hexetidine Drugs 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(III) nitrate Inorganic materials [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 1
- 239000000832 lactitol Substances 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
- 235000010448 lactitol Nutrition 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 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
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- YRIMJGKNHJOEFO-UHFFFAOYSA-N n,n-bis(1h-imidazol-2-ylmethyl)-1,1-dipyridin-2-ylethanamine Chemical compound C=1C=CC=NC=1C(C=1N=CC=CC=1)(C)N(CC=1NC=CN=1)CC1=NC=CN1 YRIMJGKNHJOEFO-UHFFFAOYSA-N 0.000 description 1
- SOCWPCWSEIVSKB-UHFFFAOYSA-N n,n-bis(1h-imidazol-2-ylmethyl)-2-phenyl-1,1-dipyridin-2-ylethanamine Chemical compound N=1C=CNC=1CN(C(CC=1C=CC=CC=1)(C=1N=CC=CC=1)C=1N=CC=CC=1)CC1=NC=CN1 SOCWPCWSEIVSKB-UHFFFAOYSA-N 0.000 description 1
- PJQKKTCJVOUVLQ-UHFFFAOYSA-N n,n-bis(pyrazol-1-ylmethyl)-1,1-dipyridin-2-ylethanamine Chemical compound C=1C=CC=NC=1C(C=1N=CC=CC=1)(C)N(CN1N=CC=C1)CN1C=CC=N1 PJQKKTCJVOUVLQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229960001774 octenidine Drugs 0.000 description 1
- SMGTYJPMKXNQFY-UHFFFAOYSA-N octenidine dihydrochloride Chemical compound Cl.Cl.C1=CC(=NCCCCCCCC)C=CN1CCCCCCCCCCN1C=CC(=NCCCCCCCC)C=C1 SMGTYJPMKXNQFY-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- RRCSSMRVSNZOFR-UHFFFAOYSA-N phenyl 3,5,5-trimethylhexanoate;sodium Chemical compound [Na].CC(C)(C)CC(C)CC(=O)OC1=CC=CC=C1 RRCSSMRVSNZOFR-UHFFFAOYSA-N 0.000 description 1
- VVTMNCICAIKIRN-UHFFFAOYSA-N phenyl benzoate;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 VVTMNCICAIKIRN-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229940084560 sanguinarine Drugs 0.000 description 1
- YZRQUTZNTDAYPJ-UHFFFAOYSA-N sanguinarine pseudobase Natural products C1=C2OCOC2=CC2=C3N(C)C(O)C4=C(OCO5)C5=CC=C4C3=CC=C21 YZRQUTZNTDAYPJ-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229940079864 sodium stannate Drugs 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- YKOLYTVUIVUUDY-UHFFFAOYSA-K sodium;zinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Na+].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YKOLYTVUIVUUDY-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000007852 tooth bleaching agent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [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 description 1
- 229940045136 urea Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 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
- 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
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/25—Silicon; Compounds thereof
Definitions
- the present invention relates to an oral composition with an improved teeth whitening effect. More particularly, it relates to an oral composition with an improved teeth whitening effect comprising, in addition to particulate abrasive cleaning agents, a safe and effective amount of peroxy compounds and certain catalysts .
- peroxy compounds in oral care compostions has already been proposed in the prior art.
- Many peroxy compounds have been suggested for whitening/bleaching human teeth, and representative examples of such peroxy compounds are hydrogen peroxide, urea peroxide, organic peracids such as perphthalic acid, diperoxycarboxylic acids, 1,12- dodecanedioic peroxy acid, peroxy acetic acid and systems comprising a peroxy compound and a peroxy acid precursor which generate peroxy acetic acid in situ, such as sodium perborate and tetraacetylethylene diamine (TAED) .
- TAED tetraacetylethylene diamine
- the use of peroxy acetic acid is suggested in particular in e.g. EP-A- 0545,594 (Colgate), which also sets out the various prior proposals, made in the art for several peroxy compounds as bleaching/whitening agent for human teeth.
- the catalyst according to the present invention provides a bleach and oxidation catalyst comprising an Fe-complex having formula (A) :
- Fe is iron in the II, III, IV or V oxidation state
- X represents a coordinating species such as H 2 0, ROH, NR 3 , RCN, OH “ , OOH “ , OOR “ , RS “ , RO “ , RCOO “ , OCN “ , SCN “ , N 3 ⁇ , CN “ , F “ , Cl “ , Br “ , I “ , O 2” , N0 3 “ , N0 2 “ , S0 4 2” , S0 3 2” , P0 4 3” or aromatic N donors such as pyridines, pyrazines, pyrazoles, i idazoles, benzimidazoles, pyrimidines, triazoles and thiazoles with R being H, optionally substituted alkyl or optionally substituted aryl ; n is an integer ranging from 0-3; Y is a counter ion, the type of which is dependent on the charge of the complex;
- L represents a ligand of general formula (B) :
- R ⁇ -R 5 which contains at least five nitrogen atoms and in which the substituent groups R ⁇ -R 5 are independently selected from hydrogen, hydroxy, halogen, nitroso, formyl , carboxyl, and esters and salts thereof, carbamoyl, sulfo, and esters and salts hereof, sulfamoyl, nitro, amino, C 0 -C 20 - alkyl -hydroxy, C 0 -C 0 -alkyl-halogen, C 0 -C 20 -alkyl-nitroso, C 0 -C 2 o-alkyl- formyl , C 0 -C 20 -alkyl -carboxyl, and esters and salts thereof, Co -C 20 - alkyl -carbamoyl, C 0 -C 20 -alkyl-sulfo, and esters and salts hereof, C 0 -C 20 -alkyl-sulf
- the peroxy compound bleach is selected from hydrogen peroxide, hydrogen peroxide-liberating or - generating compounds, peroxyacids and their salts, and mixtures thereof, optionally together with peroxyacid bleach precursors, and a catalyst according to the present invention.
- An advantage of the Fe-complex catalysts according to the present invention is that they exhibit a remarkably high oxidation activity in alkaline aqueous media in the presence of peroxy compounds .
- a second advantage of the new Fe-complex catalysts of the invention is that they show good bleaching activity at a broader pH range (generally pH 6-11) than those observed for the previously disclosed iron complexes. Their performance was especially improved at a more alkaline pH. This advantage may be particularly beneficial in view of the current chalk toothpaste formulations that employ rather alkaline conditions, as well as the tendency to shift the pH during brushing from alkaline (typically, a pH of 9) to more neutral values.
- catalysts of the invention have a relatively low molecular weight and, consequently, are very weight-effective.
- Precursors of the active Fe-complex catalysts of the invention can be any iron co-ordination complex, which, during brushing, is transformed into the active iron complex of general formula (A) .
- the precursor of the Fe-complex of the invention can be a mixture of an iron salt, such as Fe(N0 3 ) 3 , and the ligand L. It is also possible that the catalyst is present mainly in the ligand for, i.e. without complexed Fe, as this also exhibits catalytic activity since any iron present in the oral cavity e.g. in the stain can complex with the ligand.
- a preferred class of ligands is that of compounds of general formula (B) , in which R 2 , R 3 , R 4 , R 5 are independently chosen from C 0 -C 5 alkyl substituted with nitrogen-containing heterocyclic aromatic groups, such as pyridines, pyrazines, pyrazoles, imidazoles, benzimidazoles, thiazoles, triazoles and pyrimidines, in particular pyridines, and in which the substituent group Ri represents any group other than hydrogen, e.g.
- a more preferred class of ligands is that of compounds of general formula (B) , in which the substituent group Ri is selected from C 0 -C 20 alkylaryl, C 0 -C 2 o alkylheteroaryl , and C 0 - C 2 o alkyl, and in which the substituent groups R 2 , R 3 , R 4 , and R 5 are independently chosen from C 0 -C 5 alkyl substituted with a pyridine ring.
- Examples of preferred ligands in their simplest forms are: N,N-bis (pyridin-2 -yl -methyl) -1, 1-bis (pyridin-2 -yl) -1- aminoethane ; N,N-bis (pyridin-2 -yl -methyl) -1, 1-bis (pyridin-2 -yl) -2-phenyl -
- More preferred ligands are:
- the most preferred ligands are:
- BzNPy N,N-bis (pyridin-2 -yl-methyl) -1, 1-bis (pyridin-2 -yl) -2-phenyl - 1-aminoethane, hereafter referred to as BzNPy.
- Suitable counter ions are those which give rise to the formation of storage-stable solids.
- composition of the invention has particular application in toothpaste formulations, to form a new and improved composition within the purview of the invention comprising a peroxy compound bleach as defined above, the aforesaid Fe- complex catalyst having general formula (A) , particulate abrasive cleaning agents.
- the Fe-complex catalyst will be present in the oral care composition according to the invention in amounts so as to provide the required level in the mouth.
- the Fe- complex catalyst level in the composition corresponds to an iron content of from 0.0005% to 0.5% by weight.
- the Fe content in the formulation is suitably 0.0025 to 0.5%, preferably 0.005 to 0.25% by weight.
- the Fe content in the formulation is suitably 0.0005 to 0.1%, preferably 0.001 to 0.05% by weight.
- compositions of the invention are effective over a wide pH- range of between 7 and 13, with optimal pH-range lying between 8 and 10.
- the peroxy compound is preferably hydrogen peroxide but it may also be a compound which is capable of yielding hydrogen peroxide in aqueous solution.
- Hydrogen peroxide sources are well known in the art. They include the alkali metal peroxides, organic peroxides such as urea peroxide, and inorganic persalts, such as the alkali metal perborates, percarbonates, perphosphates persilicates and persulphates . Mixtures of two or more such compounds may also be suitable.
- Another suitable hydrogen peroxide generating system is a combination of a C ⁇ -C 4 alkanol oxidase and a C ⁇ -C 4 alkanol, especially a combination of methanol oxidase (MOX) and ethanol or even a similar system such as glucose oxidase and glucose.
- MOX methanol oxidase
- ethanol or even a similar system such as glucose oxidase and glucose.
- Organic peroxyacids may also be suitable as the peroxy bleaching compound.
- Such materials normally have the general formula :
- R is an alkyl- or alkylidene- or substituted alkylene group containing from 1 to about 20 carbon atoms, optionally having an internal amide linkage; or a phenylene or substituted phenylene group; and Y is hydrogen, halogen, alkyl, aryl, an imido-aromatic or non-aromatic group, a COOH or COOOH group or a quaternary ammonium group .
- Typical monoperoxy acids useful herein include, for example: (i) peroxybenzoic acid and ring-substituted peroxybenzoic acids, e.g. peroxy- ⁇ -naphthoic acid; (ii) aliphatic, substituted aliphatic and arylalkyl monoperoxyacids, e.g. peroxylauric acid, peroxystearic acid and N, N-phthaloylaminoperoxy caproic acid (PAP) ; and (iii) 6-octylamino-6-oxo-peroxyhexanoic acid.
- peroxybenzoic acid and ring-substituted peroxybenzoic acids e.g. peroxy- ⁇ -naphthoic acid
- aliphatic, substituted aliphatic and arylalkyl monoperoxyacids e.g. peroxylauric acid, peroxystearic acid and N, N-phthaloylaminoper
- Typical diperoxyacids useful herein include, for example
- inorganic peroxyacid compounds are suitable, such as for example potassium monopersulphate (MPS) . If organic or inorganic peroxyacids are used as the peroxygen compound, the amount thereof will normally be within the range of about 2-10 % by weight, preferably from 4-8 % by weight.
- MPS potassium monopersulphate
- the bleaching composition of the invention can be suitably formulated to contain from 0.001 to 15% , preferably from 0.01 to 5% by weight, of the peroxy bleaching agent .
- Peroxyacid bleach precursors are known and amply described in literature, such as in GB-A-836988 ; GB-A-86 , 798 ; GB-A- 907,356; GB-A-1 , 003 , 310 and GB-A-1 , 519 , 351 ; DE-A-3 , 337 , 921 ; EP-A-0,185,522; EP-A-0 , 174 , 132 ; EP-A- 0 , 120 , 591 ; and US-A- 1,246,339; US-A-3 , 332 , 882 ; US-A-4 , 128 , 494 ; US-A-4 , 412 , 934 and US-A-4, 675, 393.
- peroxyacid bleach precursors are those of the cationic i.e. quaternary ammonium substituted peroxyacid precursors as disclosed in US-A-4 , 751 , 015 and US- A-4, 397, 757, in EP-A-0,284,292 and EP-A-331 , 229.
- peroxyacid bleach precursors of this class are:
- peroxyacid bleach precursors can be used in the present invention, although some may be more preferred than others .
- the preferred classes are the esters, including acyl phenol sulphonates and acyl alkyl phenol sulphonates; the acyl -amides; and the quaternary ammonium substituted peroxyacid precursors.
- Examples of said preferred peroxyacid bleach precursors or activators are sodium-4-benzoyloxy benzene sulphonate (SBOBS) ; N, N, N 'N' -tetraacetyl ethylene diamine (TAED) ; sodium- 1 -methyl -2 -benzoyloxy benzene-4-sulphonate; sodium-4- methyl-3-benzoloxy benzoate; 2- (N,N,N-trimethyl ammonium) ethyl sodium-4 -sulphophenyl carbonate chloride (SPCC) ; trimethyl ammonium toluyloxy-benzene sulphonate; sodium nonanoyloxybenzene sulphonate (SNOBS); and sodium 3,5,5- trimethyl hexanoyl-oxybenzene sulphonate (STHOBS) .
- the precursors may be used in an amount of up to 12 %, preferably from 1-10 % by weight, of the composition.
- the preferred peroxy compound is hydrogen peroxide
- the preferred catalyst is Fe N,N-bis (pyridin-2 -yl -methyl ) -1, 1 - bis (pyridin-2-yl) -1 -aminoethane ( FeMeN4Py )
- the catalyst is used generally in an amount of 0.0001 to 5 % by weight, preferably 0.025 to 1.5 % by weight, and particulary preferably 0.005 to 1 % by weight of the oral care composition.
- the oral compositions can be formulated in any suitable application form, such as gels, mouthwashes, toothpowders and toothpastes.
- An alternative product form may be an adhesive patch which fits over the tooth surface and keeps the bleaching agents in contact with the tooth surface for a short period of time, e.g. over-night. They may be formulated into a single formulation or they may be formulated for multi compartment containers into different formulations, e.g. one containing the peroxy compound and ingredients compatible therewith, and another containing the remaining ingredients.
- the oral care compositions of the present invention may furthermore comprise optional, conventional ingredients such as pharmaceutically acceptable carriers like starch, sucrose, water or water/alcohol systems etc.. Small amounts of surfactants may also be included, such as anionic, nonionic and amphoteric surfactants. When formulated into a dentifrice, such formulation may contain all the usual dentifrice ingredients.
- particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, calcium pyrophosphates hydroxyapatites , trimetaphosphates, insoluble hexametaphosphates, agglomerated particulate abrasive materials and so on, usually in amounts between 5 and 60 % by weight.
- the dentifrice formulations may comprise humectants such as glycerol, sorbitol, propyleneglycol , xylitol, lactitol and so on.
- Binders and thickeners such as sodium carboxymethyl- cellulose, xanthan gum, gum arabic etc. may also be included, as well as synthetic polymers such as polyacrylates and carboxyvinyl polymers such as Carbopol ® .
- Flavours such as peppermint and spearmint oils may also be included, as well as preservatives, opacifying agents, colouring agents, pH-adjusting agents, sweetening agents and so on.
- Stabilising agents for the organic peroxy compounds such as dipicolinic acid or sodium stannate may also be usefully included.
- Anti -bacterial agents may also be included such as Triclosan, chlorhexidine, copper-, zinc- and stannous salts such as zinc citrate, sodium zinc citrate and stannous pyrophosphate, sanguinarine extract, metronidazole.
- Further examples of anti -bacterial agents are quaternary ammonium compounds such as cetylpyridinium chloride; bis-guanides such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; halogenated bisphenolic compounds such as 2,2' methylenebis- (4-chloro-6-bromophenol) .
- Polymeric compounds which can enhance the delivery of active ingredients such as anti -bacterial agents can also be included.
- examples of such polymers are copolymers of polyvinylmethylether with maleic anhydride and other similar delivery enhancing polymers, e.g. those described in DE-A- 3,942,643 (Colgate)
- anti- inflammatory agents such as ibuprofen, flurbiprofen, aspirin, indomethacin etc. may also be included.
- Anti -caries agents such as sodium- and stannous fluoride, aminefluorides, monosodiumfluorophosphate, casein, plaque buffers such as urea, calcium lactate, calcium glycerophosphate, strontium polyacrylates may also be included.
- Other optional ingredients include vitamins such as Vitamin C, and plant extracts.
- Desensitising agents such as potassium citrate, potassium chloride, potasium tartrate, potassium bicarbonate, potassium oxalate, potassium nitrate as well as strontium salts may also be included.
- Buffers and salts to buffer the pH and ionic strength of the compositions may also be included.
- the pH of the compositions usually ranges from 5-10, preferably 6-9 and especially preferably 7-8.5.
- Liposomes and other encapsulates may also be used to improve delivery or stability of active ingredients.
- the oral compositions may comprise anti- calculus agents such as alkalimetal pyrophosphates, hypophosphite-containing polymers, organic phosphonates, alkalimetal tripolyphosphates, phosphocitrates etc..
- anti- calculus agents such as alkalimetal pyrophosphates, hypophosphite-containing polymers, organic phosphonates, alkalimetal tripolyphosphates, phosphocitrates etc.
- compositions may comprise functional biomolecules such as bacteriocins , antibodies, enzymes and so on.
- effervescing systems such as sodium bicarbonate/citric acid systems, colour change systems, and so on.
- compositions may also contain a bleach precursor.
- the oral care composition When formulated as a mouthwash, the oral care composition usually comprises a water/alcohol solution, flavour, humectant, sweetener and colorant.
- the invention also includes the use of the combination of a peroxy compound and a catalyst according to the invention as teeth whitening effect.
- Example I The present invention will further be illustrated by way of Example .
- Example I Example I
- the catalyst was further evaluated as follows
- Synthetic hydroxyapatite discs (an alternative mimic of the tooth surface) were polished and placed in sterile saliva overnight to form a pellicle. They were then stained by immersing in a tea/coffee mixture for four days before being immersed in experimental bleach solutions. The change in colour of the discs was measured using a Minolta chromameter and the percentage stain removal was calculated.
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Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00914175A EP1165029A1 (en) | 1999-04-01 | 2000-03-31 | Oral composition with an improved teeth whitening effect |
BR0009452-8A BR0009452A (en) | 1999-04-01 | 2000-03-31 | Oral care composition with an increased teeth whitening effect, and use of a peroxide compound and a catalyst |
AU35585/00A AU3558500A (en) | 1999-04-01 | 2000-03-31 | Oral composition with an improved teeth whitening effect |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99302582 | 1999-04-01 | ||
EP99302582.4 | 1999-04-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000059461A1 true WO2000059461A1 (en) | 2000-10-12 |
Family
ID=8241307
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/002858 WO2000059461A1 (en) | 1999-04-01 | 2000-03-31 | Oral composition with an improved teeth whitening effect |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1165029A1 (en) |
CN (1) | CN1345223A (en) |
AU (1) | AU3558500A (en) |
BR (1) | BR0009452A (en) |
ID (1) | ID30331A (en) |
WO (1) | WO2000059461A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6290935B1 (en) * | 2000-07-21 | 2001-09-18 | Colgate-Palmolive Company | Dual component oral composition having accelerated tooth whitening effect |
WO2002047638A1 (en) * | 2000-12-15 | 2002-06-20 | Unilever N.V. | Oral bleaching composition |
US6709647B2 (en) | 2001-01-16 | 2004-03-23 | Unilever Home & Personal Care Usa, A Division Of Conopco, Inc. | Antimicrobial deodorant compositions |
WO2009109533A1 (en) * | 2008-03-07 | 2009-09-11 | Basf Se | Bleach catalysts and their use as teeth whitening agents |
EP3127583A1 (en) * | 2013-06-24 | 2017-02-08 | The Procter and Gamble Company | A method of demonstrating stain-proof efficacy of an oral care composition |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112019007889A2 (en) | 2016-10-26 | 2019-07-09 | Procter & Gamble | teeth whitening |
CN110799248B (en) * | 2017-06-19 | 2023-06-16 | 高露洁-棕榄公司 | Oral care product and whitening composition thereof |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0332551A1 (en) * | 1988-02-11 | 1989-09-13 | RECHERCHE- CONCEPTION- DEVELOPPEMENT "R.C.D. LABO" S.à.r.l. | Solid galenic forms containing at least one peroxidic substance and a transition metal salt |
EP0516872A1 (en) * | 1990-02-02 | 1992-12-09 | Demetron Research Corp. | Dental composition and method for bleaching teeth |
EP0545594A1 (en) * | 1991-11-22 | 1993-06-09 | Colgate-Palmolive Company | Oral composition having improved tooth whitening effect |
WO1995034628A1 (en) * | 1994-06-13 | 1995-12-21 | Unilever N.V. | Bleach activation |
WO1996005802A2 (en) * | 1994-08-22 | 1996-02-29 | Unilever N.V. | Teeth whitening composition containing organic peroxyacids |
JPH1157488A (en) * | 1997-08-26 | 1999-03-02 | Mitsui Chem Inc | Catalyst composition against bleaching action of peroxide |
EP0909809A2 (en) * | 1997-10-01 | 1999-04-21 | Unilever Plc | Bleach activation |
JPH11130649A (en) * | 1997-10-23 | 1999-05-18 | Lion Corp | Detergent for artificial tooth |
-
2000
- 2000-03-31 AU AU35585/00A patent/AU3558500A/en not_active Abandoned
- 2000-03-31 CN CN 00805516 patent/CN1345223A/en active Pending
- 2000-03-31 WO PCT/EP2000/002858 patent/WO2000059461A1/en not_active Application Discontinuation
- 2000-03-31 EP EP00914175A patent/EP1165029A1/en not_active Withdrawn
- 2000-03-31 BR BR0009452-8A patent/BR0009452A/en not_active Application Discontinuation
- 2000-03-31 ID IDW00200102098A patent/ID30331A/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0332551A1 (en) * | 1988-02-11 | 1989-09-13 | RECHERCHE- CONCEPTION- DEVELOPPEMENT "R.C.D. LABO" S.à.r.l. | Solid galenic forms containing at least one peroxidic substance and a transition metal salt |
EP0516872A1 (en) * | 1990-02-02 | 1992-12-09 | Demetron Research Corp. | Dental composition and method for bleaching teeth |
EP0545594A1 (en) * | 1991-11-22 | 1993-06-09 | Colgate-Palmolive Company | Oral composition having improved tooth whitening effect |
WO1995034628A1 (en) * | 1994-06-13 | 1995-12-21 | Unilever N.V. | Bleach activation |
WO1996005802A2 (en) * | 1994-08-22 | 1996-02-29 | Unilever N.V. | Teeth whitening composition containing organic peroxyacids |
JPH1157488A (en) * | 1997-08-26 | 1999-03-02 | Mitsui Chem Inc | Catalyst composition against bleaching action of peroxide |
EP0909809A2 (en) * | 1997-10-01 | 1999-04-21 | Unilever Plc | Bleach activation |
JPH11130649A (en) * | 1997-10-23 | 1999-05-18 | Lion Corp | Detergent for artificial tooth |
Non-Patent Citations (2)
Title |
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PATENT ABSTRACTS OF JAPAN vol. 1999, no. 08 30 June 1999 (1999-06-30) * |
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 10 31 August 1999 (1999-08-31) * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6290935B1 (en) * | 2000-07-21 | 2001-09-18 | Colgate-Palmolive Company | Dual component oral composition having accelerated tooth whitening effect |
WO2002047638A1 (en) * | 2000-12-15 | 2002-06-20 | Unilever N.V. | Oral bleaching composition |
US6475472B2 (en) | 2000-12-15 | 2002-11-05 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Oral bleaching composition |
US6709647B2 (en) | 2001-01-16 | 2004-03-23 | Unilever Home & Personal Care Usa, A Division Of Conopco, Inc. | Antimicrobial deodorant compositions |
WO2009109533A1 (en) * | 2008-03-07 | 2009-09-11 | Basf Se | Bleach catalysts and their use as teeth whitening agents |
EP3127583A1 (en) * | 2013-06-24 | 2017-02-08 | The Procter and Gamble Company | A method of demonstrating stain-proof efficacy of an oral care composition |
Also Published As
Publication number | Publication date |
---|---|
BR0009452A (en) | 2002-01-08 |
CN1345223A (en) | 2002-04-17 |
ID30331A (en) | 2001-11-22 |
EP1165029A1 (en) | 2002-01-02 |
AU3558500A (en) | 2000-10-23 |
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