CN1170348A - 口腔用组合物 - Google Patents
口腔用组合物 Download PDFInfo
- Publication number
- CN1170348A CN1170348A CN95196900A CN95196900A CN1170348A CN 1170348 A CN1170348 A CN 1170348A CN 95196900 A CN95196900 A CN 95196900A CN 95196900 A CN95196900 A CN 95196900A CN 1170348 A CN1170348 A CN 1170348A
- Authority
- CN
- China
- Prior art keywords
- composition
- alkyl
- group
- dimethicone copolyol
- sodium
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 24
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 24
- 229940008099 dimethicone Drugs 0.000 claims abstract description 22
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims abstract description 19
- 239000000551 dentifrice Substances 0.000 claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000000606 toothpaste Substances 0.000 claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000011230 binding agent Substances 0.000 claims abstract description 10
- 239000003906 humectant Substances 0.000 claims abstract description 10
- 239000002324 mouth wash Substances 0.000 claims abstract description 10
- 239000004094 surface-active agent Substances 0.000 claims abstract description 10
- 239000000253 Denture Cleanser Substances 0.000 claims abstract description 9
- 239000003082 abrasive agent Substances 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 229940051866 mouthwash Drugs 0.000 claims abstract description 8
- 235000003599 food sweetener Nutrition 0.000 claims abstract description 7
- 239000003765 sweetening agent Substances 0.000 claims abstract description 7
- 229940034610 toothpaste Drugs 0.000 claims abstract description 7
- 235000015218 chewing gum Nutrition 0.000 claims abstract description 5
- 235000009508 confectionery Nutrition 0.000 claims abstract description 5
- 229940112822 chewing gum Drugs 0.000 claims abstract description 4
- 230000002272 anti-calculus Effects 0.000 claims abstract description 3
- -1 zirconium silicates Chemical class 0.000 claims description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000002882 anti-plaque Effects 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229920000388 Polyphosphate Polymers 0.000 claims description 4
- 235000011180 diphosphates Nutrition 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- 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 claims description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 229940085262 cetyl dimethicone Drugs 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 125000005341 metaphosphate group Chemical group 0.000 claims description 2
- 239000002952 polymeric resin Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 229910000391 tricalcium phosphate Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- ROPDWRCJTIRLTR-UHFFFAOYSA-L calcium metaphosphate Chemical compound [Ca+2].[O-]P(=O)=O.[O-]P(=O)=O ROPDWRCJTIRLTR-UHFFFAOYSA-L 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 1
- 239000000843 powder Substances 0.000 abstract description 5
- 229920005862 polyol Polymers 0.000 abstract description 3
- 150000003077 polyols Chemical class 0.000 abstract description 3
- 239000007844 bleaching agent Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000002243 precursor Substances 0.000 description 14
- 239000000796 flavoring agent Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 230000000845 anti-microbial effect Effects 0.000 description 8
- 239000004088 foaming agent Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 150000002634 lipophilic molecules Chemical class 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 6
- 239000004075 cariostatic agent Substances 0.000 description 6
- 239000002738 chelating agent Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 239000002826 coolant Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 235000013355 food flavoring agent Nutrition 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BGRWYDHXPHLNKA-UHFFFAOYSA-N Tetraacetylethylenediamine Chemical compound CC(=O)N(C(C)=O)CCN(C(C)=O)C(C)=O BGRWYDHXPHLNKA-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 229940041616 menthol Drugs 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 150000004967 organic peroxy acids Chemical class 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 150000004965 peroxy acids Chemical class 0.000 description 4
- 238000005498 polishing Methods 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- 208000006558 Dental Calculus Diseases 0.000 description 3
- 229940120146 EDTMP Drugs 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 235000001465 calcium Nutrition 0.000 description 3
- 235000010216 calcium carbonate Nutrition 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000701 coagulant Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 206010006326 Breath odour Diseases 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- 108010001682 Dextranase Proteins 0.000 description 2
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000001744 Sodium fumarate Substances 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 210000004268 dentin Anatomy 0.000 description 2
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000005342 perphosphate group Chemical group 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920005646 polycarboxylate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229940048084 pyrophosphate Drugs 0.000 description 2
- 108700004121 sarkosyl Proteins 0.000 description 2
- 229910002028 silica xerogel Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 235000019294 sodium fumarate Nutrition 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000004685 tetrahydrates Chemical class 0.000 description 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229960003500 triclosan Drugs 0.000 description 2
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- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 1
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- 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
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 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
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- 239000009637 wintergreen oil Substances 0.000 description 1
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
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Classifications
-
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Abstract
一种牙膏、牙粉、液体洁牙剂、漱口液、托牙清洁剂、口香糖或糖果形式的口腔用组合物,它含有一种或多种选自磨料、粘合剂、保湿剂、表面活性剂、氟离子源、抗牙石剂和甜味剂的口腔用组合物组分,还含有说明书中所定义的二甲聚硅氧烷共聚多元醇。
Description
技术领域
本发明涉及口腔用组合物，如牙膏、牙粉、液体洁牙剂、漱口液、托牙(denture)清洁剂、口香糖、糖果等。具体地，本发明涉及具有更高的抗齿菌斑活性以及优异的清洗性能、物理特性和使用性能的口腔用组合物。
背景
牙斑是当粘附在表膜上的细菌在牙齿表面上形成蛋白质膜时所引起的。粘附的细菌代谢食物成分，并繁殖和聚集从而形成牢固的沉积物，即已知的牙斑。牙斑一般由细菌、细菌终产物如多糖、无机盐、和唾液蛋白所构成。牙斑细菌将食物碳水化合物酵解成有机酸，这些有机酸使牙釉质发生去矿质作用，从而导致牙齿损坏。
牙积石大体上是已和磷酸钙盐矿物化的牙斑。当牙积石成熟和硬化时，它会因吸收食物中的生色团而明显着色。除了外观难看之外，牙床线上的牙积石沉积物是导致齿龈炎和牙周疾病的病因。除了牙斑造成的卫生和健康问题之外，研究已表明，口臭的主要原因，是正常的健康口腔中不断脱落的死细胞物质的滞留及随后的降解。
现代的牙科卫生和牙齿制剂一般都含有抗牙斑剂和/或抗牙石剂，以及抗微生物剂和芳香剂。抗微生物作用可影响牙斑的形成，这或者通过减少口腔/牙齿中的细菌数目，或者通过杀灭那些陷在膜中的细菌以防止其进一步生长和代谢。
芳香剂通过去异味作用而减弱口臭问题。某些抗微生物剂如薄荷脑，也可作为口气除臭剂。然而，抗微生物剂的效力主要取决于它们的在口腔内/牙中滞留情况，尤其是它们在牙齿表面上的滞留时间或当牙斑形成的情况下在牙或托牙上的滞留时间。
已知牙用制剂的典型缺点是，只有较短的时间(在此期间牙齿被清洁或口腔被漱洗)可让制剂中的抗微生物剂发挥作用。该问题因下列事实而加重了：洁牙剂的使用不频繁：大多数是每天使用一次或许二次。因此，对于大多数人而言，在刷牙之间的长时间提供了最佳的牙斑形成条件。
因此，需要开发一种口腔用组合物，它具有长时间的、残余抗微生物效果和/或芳香效果。
已知可在洁牙剂组合物中加入(聚)硅氧烷(silicone)，据称可涂覆牙齿并防止蛀牙和着色。例如，GB-A-689,679公开了一种漱口液，它含有有机聚硅氧烷，以防止下列物质粘附于牙齿或从牙齿上去除下列物质：焦油、色斑、牙石和食物颗粒。漱口液可含有杀菌剂如麝香草酚，和清新芳香剂。
US-A-2,806,814公开了牙用制剂，它同时含有氨基羧酸化合物的高级脂族酰胺作为活性成分以及聚硅氧烷化合物。该专利指出，已提出聚硅氧烷化合物来防止焦油、色斑、牙石等粘附于牙齿或者便于从牙齿上去除这些物质。据说，聚硅氧烷化合物可作为协合剂而改善活性成分的抗细菌活性和抑酸活性。据说二甲基聚硅氧烷特别有效。可含有食用香料油和/或薄荷脑。
US-A-3624120公开了将环状聚硅氧烷的季铵盐用作阳离子表面活性剂、杀细菌剂和抗龋剂。
因此，本发明提供了一类口腔用组合物，它对牙斑、粘液和细菌沉积物具有更佳的效果而且同时它还提供了优异的清洁性能、物理性能和使用性能。
本发明还提供了一类口腔用组合物，它含有亲脂的化合物如香味剂、生理清凉剂或抗微生物剂，而且它对牙齿和托牙具有更佳的直接亲和性、作用力和/或效力。
发明概述
在本发明的第一个方面，提供了一种牙膏、牙粉、液体洁牙剂、漱口液、托牙清洁剂、口香糖或糖果形式的口腔用组合物，它含有一种或多种选自磨料、粘合剂、保湿剂、表面活性剂、氟离子源、抗牙石剂和甜味剂的口腔用组合物组份，还含有选自式(I)所示烷基-和烷氧基-二甲聚硅氧烷共聚多元醇的二甲聚硅氧烷共聚多元醇：
其中，X选自氢，具有1至约16个碳原子的烷基、烷氧基和酰基；Y选自具有约8至约22个碳原子的烷基和烷氧基；n为约0至约200；m为约1至约40；q为约1至约100；残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000，较佳为约250至约1000，且x和y为使氧化乙烯∶氧化丙烯的重量比达到约100∶0至约0∶100(较佳达到约100∶0至约20∶80)的数字。
在本发明的另一方面，提供了一种牙膏、牙粉、液体洁牙剂、漱口液、托牙清洁剂、口香糖或糖果形式的口腔用组合物，它含有选自香味剂、生理清凉剂和抗微生物化合物的口腔用组合物组份，以及选自式(I)所示烷基-和烷氧基-二甲聚硅氧烷共聚多元醇的二甲聚硅氧烷共聚多元醇。
本文中所有的百分比和比率都是按总组合物的重量计算，除非另外说明。
因此，本发明的口腔用组合物含有二甲聚硅氧烷共聚多元醇抗牙斑剂，而优选的组合物还含有亲脂的化合物和/或一种或多种选自磨料、粘合剂、保湿剂、表面活性剂、氟离子源、抗牙石剂和甜味剂的口腔用组合物组份。这些物质中的每一种将会依次叙述。
一般，二甲聚硅氧烷共聚多元醇选自式(I)所示烷基-和烷氧基-二甲聚硅氧烷共聚多元醇：
其中，X选自氢，具有1至约16个碳原子的烷基、烷氧基和酰基；Y选自具有约8至约22个碳原子的烷基和烷氧基；n为约0至约200；m为约1至约40；q为约1至约100；残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000，较佳为约250至约1000，且x和y为使氧化乙烯∶氧化丙烯的重量比达到约100∶0至约0∶100(较佳达到约100∶0至约20∶80)的数字。
在较佳的实施方案中，二甲聚硅氧烷共聚多元醇选自C12-C20烷基二甲聚硅氧烷共聚多元醇及其混合物。极佳的为十六烷基二甲聚硅氧烷共聚多元醇，其商品名为Abil EM90。二甲聚硅氧烷共聚多元醇的量按重量计一般为约0.1至约25％，较佳为约0.1％至约5％，更佳为约0.5％至约1.5％。
本发明的口腔用组合物最好还含有亲脂化合物。一般而言，适用于此处的亲脂化合物是油样的材料，它们在二甲聚硅氧烷共聚多元醇中可溶，较佳地溶解度在25℃时至少约1％，更佳地至少约5％(重量)。优选的亲脂化合物选自香味剂、生理清凉剂和抗微生物化合物。二甲聚硅氧烷共聚多元醇用于提高亲脂化合物对牙齿和/或托牙的直接亲和性，从而提高和/或持续保持香味作用和抗微生物效力。
适用于本发明的亲脂香味剂包括一种或多种选自下列的香味组份：冬青油、牛至油、桂叶油、薄荷油、留兰香油、丁子香油、沙尔维亚油、黄樟油、柠檬油、橘油、茴香油、苯甲醛、苦杏仁油、樟脑、雪松叶油、甘牛至油、香茅油、熏衣草油、芥末油、松油、松针油、迷迭香油、百里香油、肉桂叶油，以及它们的混合物。
适用于本发明的亲脂抗微生物剂包括：麝香草酚、薄荷脑、二氯苯氧氯酚、4-己基间苯二酚、苯酚、桉叶油素、苯甲酸、过氧化苯酰、对羟苯甲酸丁酯、对羟苯甲酸甲酯、对羟苯甲酸丙酯、水杨酰胺，以及它们的混合物。
适用于本发明的亲脂生理清凉剂包括：羧酰胺(carboxamide)、薄荷烷酯和薄荷烷醚，以及它们的混合物。
适用于此处的薄荷烷醚选自具有下式的种类：
其中，R5是可任意地被羟基取代的、含有25个碳原子之内的，较佳地5个碳原子之内的脂族基，而X是氢或羟基。比如那些可从Takasago InternationalCorporation以商品名Takasago购得的种类。一种用于本发明组合物中的特别优选的清凉剂是Takasago 10[3-1-薄荷氧基丙-1，2-二醇(MPD)]。MPD是1-薄荷醇的单甘油衍生物，它具有优异的冷却性。
发现最有用的羧酰胺是在US-A-4,136,163(1979年1月23日，授予Wason等人)和US-A-4,230，688(1980年10月28日，授予Rawsell等人)中所述的种类。
在本发明组合物中亲脂化合物的用量一般为约0.01-10％，较佳地为约0.05-5％，更佳地为约0.1-3％(重量)。
牙膏、托牙清洗液和膏体等形式的组合物一般含有粘合剂和增稠剂。适用于此处的粘合剂包括：羧乙烯聚合物、角叉菜胶、羟乙基纤维素和纤维素醚的水溶性盐如羧甲基纤维素钠和羧甲基羟乙基纤维素钠。还可使用天然胶，如刺梧桐胶、黄原胶、阿拉伯树胶和黄蓍胶。胶体状硅酸镁铝或细氧化硅可用作增稠剂的一部分以进一步提高质感。粘合剂/增稠剂的用量为总组合物重量的约0.1-5.0％，较佳地为约0.1-1％。
还需要在牙膏中加入某些保湿剂以防组合物在暴露于空气时发生硬化。某些保湿剂还可赋予牙膏组合物所需的甜味。液体洁牙剂和漱口液也可含有一定量的保湿剂。适用的保湿剂包括：甘油、山梨糖醇、木糖醇、聚乙二醇、丙二醇、和其它可食用的多羟基醇类，以及它们的混合物。当存在时，保湿剂一般占本发明组合物的约10％-70％(重量)。
牙膏、液体洁牙剂和液体或膏体形式的托牙清洁剂一般可含有研磨抛光材料。可用于此处的研磨抛光材料可以是任何材料，只要其不过分研磨牙质或托牙丙烯酸材料。例如有：包括干凝胶、水凝胶、气凝胶及沉淀氧化硅，碳酸钙和碳酸镁，钙的正磷酸、焦磷酸、偏磷酸及多磷酸盐如二水合正磷酸二钙、焦磷酸钙、磷酸三钙和多偏磷酸钙，不溶性多偏磷酸钠，氧化铝及水合氧化铝如三水合α氧化铝，硅铝酸盐如煅烧的硅酸铝和硅酸铝，镁和锆的硅酸盐如三硅酸镁和热固性聚合树脂如脲和甲醛的微粒缩合产物、聚丙烯酸甲酯、粉末状的聚乙烯和其他在1962年12月25日的美国专利3,070,510中所揭示的其他物质。也可使用这些磨料的混合物。研磨抛光材料的一般的平均粒度为0.1-30微米，较佳地为约5-15微米。
各种类型的氧化硅牙齿磨料可以提供优异的牙齿清洁和抛光性能而不会过分磨损牙珐琅质或牙质。氧化硅磨料可以是沉淀氧化硅或诸如氧化硅干凝胶之类的氧化硅凝胶，如在1970年3月2日授权于Pader等人的美国专利3,538,230和1975年6月21日的授予DiGiulio的美国专利3,862,307所述的，比如W.R.Grace & Company，Davison Chemical Division的商品名为“Syloid”的氧化硅干凝胶。合适的沉淀氧化硅材料包括J.M.Huber Corporation的商品名为“Zeodent”，尤其是牌号为“Zeodent 119”的氧化硅。这些氧化硅磨料在美国专利4,340,583(1982年7月29日)中有描述。
从提供高清洗性能和与抗牙斑剂的优异相容性方面考虑，此处特别优选的是碳酸钙磨料。
在本发明的洁牙剂制剂中，磨料的一般存在量为约10-70％，较佳地为15-25％(重量)。
本发明的组合物还含有表面活性剂。合适的表面活性剂是那些在大的pH范围内可发泡且相当稳定的种类，其中包括非皂用阴离子型、非离子型、阳离子型、两性离子型和两性有机合成清洁剂。许多的此类合适试剂公开于Gieske等人的美国专利4,051,234(1977年9月27日)。
合适的表面活性剂例子包括：烷基硫酸盐；环氧乙烷与脂肪酸、脂族醇、脂族酰胺、多醇(如脱水山梨糖醇单硬脂酸酯、脱水山梨糖醇油酸酯)的缩合产物、与烷基苯酚的缩合产物(如Tergitol)和聚环氧丙烷或聚氧化丁烯(如Pluronics)；氧化胺如氧化二甲椰子胺、氧化二甲基月桂基胺和氧化椰子烷基二甲基胺(cocoalkyldimethyl amine oxide)(Aromox)；聚山梨醇酯如Tween 40和Tween80(Hercules)；山梨糖醇硬脂酸酯、山梨糖醇单油酸酯等；肌氨酸盐如椰子酰肌氨酸钠(sodium cocoylsarcosinate)、月桂酰肌氨酸钠(Hamposyl-95 ex W.R.Grace)；阳离子表面活性剂如氯化鲸腊基吡啶鎓、溴化鲸腊基三甲铵、氯化二-异丁基苯氧基乙氧基乙基-二甲基苄铵和硝酸椰子烷基三甲铵。
还可在本发明的组合物中加入可溶性氟离子源。可溶性氟离子源的用量应足够以提供约50-3500ppm的氟离子。优选的氟化物是氟化钠、氟化亚锡、氟化铟、氟化锌铵、氟化锡铵、氟化钙和单氟磷酸钠。在1960年7月26日授予Norris等人的美国专利2,946,735和1972年7月18日授予Widder等人的美国专利3,678,154中公开了这些盐及其他盐。
本发明的组合物还可含有防龋剂。合适的防龋剂包括焦磷酸二碱金属盐和焦磷酸四碱金属盐，如在EP-A-097476中揭示的。具体的盐包括焦磷酸四碱金属盐、焦磷酸二氢二碱金属盐、焦磷酸一氢三碱金属盐及其混合物，其中碱金属是钠或钾。盐可以以水合和非水合形式使用。用于这些组合物中的焦磷酸盐的用量可以是任何有效的数量，而且按组合物的重量计，一般应足以在组合物中提供至少1.0％P2O7 -4，较佳地为约1.5-1.0％，更佳地为约3-6％。焦磷酸盐在Kirk & Othmer，化学技术百科全书(Encyclopedia of Chemical Technology)，第二版，15卷，Interscience Publishers(1968)中有详细描述。
其他适用于本发明的防龋剂是锌盐。在美国专利4,100,269、4,416,867、4,425,325和4,339,432中揭示了锌盐。一种优选的锌试剂品种是柠檬酸锌。锌化合物的用量应足以提供约0.01-4％，较佳地约0.05-1％(重量)的锌离子。
其他合适的防龋剂包括合成的阴离子聚合物(包括聚丙烯酸酯以及马来酸酐或酸与甲基乙烯基醚的共聚物(如Gantrez)如在美国专利4,627,977中所述)，聚氨基丙磺酸、多磷酸盐(如三聚磷酸盐、六偏磷酸盐)、二膦酸盐(如EHDP、AHP)、多肽(如聚天冬氨酸和聚谷氨酸)，以及它们的混合物。
可以使用的香味剂包括天冬酰苯丙氨酸甲酯、乙酰舒泛、糖精、葡萄糖、果糖和环己烷氨基磺酸钠。甜味剂的用量一般为组合物的约0.005-2重量％。
其他用于本发明的可选组份包括水溶性抗菌剂如二葡萄糖酸洗必泰、季铵抗菌化合物和水溶性的某些金属离子源如锌、铜、银和亚锡(如氯化锌、氯化铜和氯化亚锡，以及硝酸银)；颜料如二氧化钛；可口腔使用的染料/着色剂如FD&C蓝#1、FD&C黄#10、FD&C红#40；抗氧化剂，维生素如维生素C和E，其他抗牙斑剂如亚锡盐、铜盐、锶盐和镁盐；pH调节剂，防龋剂如尿素、甘油磷酸钙、三偏磷酸钠，植物提取物，用于敏感牙齿的脱敏剂如硝酸钾和柠檬酸钾，以及它们的混合物。
通常，漱口液含有上述的水/醇溶液、香味剂、保湿剂、甜味剂、起泡剂、和着色剂。
漱口液可含有约0-60％，较佳地约5-30％(重量)的乙醇。
本发明的托牙清洁剂还可含有一种或多种漂白剂、有机过氧酸前体、起泡剂和螯合剂等。
漂白剂可以是无机过酸盐形式，而且可以选自任何公知的、用于托牙清洁剂的漂白剂，如碱金属和铵的过(二)硫酸盐、过硼酸盐、过碳酸盐和过磷酸盐，以及碱金属和碱土金属的过氧化物。合适的漂白剂例子包括钾、铵、钠和锂的过硫酸盐和过硼酸盐一水合和四水合物，焦磷酸钠过氧水合物(peroxyhydrate)以及镁、钙、锶和锌的过氧化物。其中，优选用于此处的是碱金属的过硫酸盐、过硼酸盐及它们的混合物，特别优选的是碱金属的过硼酸盐。事实上，本发明的一个特征是，即使在没有碱金属的过硫酸盐时，此处的片剂组合物也可提供优异的抗微生物性。
漂白剂在全部组合物中的数量一般为5-70％，较佳地为约10-50％。在含有碱金属的过硫酸盐和过硼酸盐的混合物的组合物中，总过硫酸盐∶过硼酸盐之比宜为约5∶1-1∶5，较佳地为约2∶1-1∶2。
托牙清洁组合物还可加入起泡剂，即在水存在时会释放出二氧化碳或氧气并起泡的材料。起泡剂可选自在酸性、中性或碱性pH条件下有效的气泡发生剂，但最好它由在酸性或中性pH条件下有效或最有效的发生剂和在碱性pH条件下有效或最有效的发生剂一起构成。在酸性或中性pH条件下有效的起泡剂包括：至少一种碱金属的碳酸盐或碳酸氢盐(如碳酸氢钠、碳酸钠、倍半碳酸钠、碳酸钾、碳酸氢钾或它们的混合物)和至少一种无毒的、生理上可接受的有机酸(如酒石酸、富马酸、柠檬酸、苹果酸、马来酸、葡萄糖酸、琥珀酸、水杨酸、己二酸或氨基磺酸，富马酸钠、钠或钾的酸性磷酸盐，盐酸甜菜碱，及它们的混合物)的组合。其中，优选苹果酸。在碱性pH条件下有效的起泡剂包括：前面所述的过酸盐如碱金属和碱土金属的过氧化硼酸盐和过硼酸盐、过硫酸盐、过碳酸盐、过磷酸盐以及它们的混合物，例如碱金属的过硼酸盐(无水的，一水合物或四水合物)和单过硫酸盐如E I du Pont de Nemours Co.生产的Caroat R(它是单过硫酸盐、硫酸钾和硫酸氢钾的2∶1∶1混合物，其活性氧含量为约4.5％。)的混合物。
在片剂形式的优选托牙清洁组合物中，起泡剂是固体碱性材料，它在水存在时释放出二氧化碳或氧气和气泡。合适的是，固体碱性材料中加入了碳酸(氢)盐/酸起泡对，它还可任选地与过硼酸盐/过硫酸盐氧气起泡剂组合使用。为了实现最佳的清洗性和抗微生物性，起泡剂的组合使用对于得到最佳的溶解特性和pH条件是有利的。碳酸(氢)盐组份一般占总组合物的约5-65％，较佳地为约25-55％；而酸组份一般占总组合物的约5-50％，较佳地为约10-30％。
本发明的托牙清洁组合物还可添加此类制剂的其他已知组份。一种特别优选的额外组份是有机过酸(peroxyacid)前体，一般它们可被定义为在下列的过酸形成试验中滴定度至少为1.5毫升0.1N硫代硫酸钠。
通过将下列物质溶解在1000毫升蒸馏水中而制备测试溶液：
| 焦磷酸钠(Na4P2O7·10H2O) | 2.5克 |
| 过硼酸钠(NaBO2·H2O2·3H2O)，有10.4％的可供氧 | 0.615克 |
| 十二烷基苯磺酸钠 | 0.5克 |
向60℃的该溶液中加入一定量的活化剂，从而对于每个存在的可供氧原子引入一分子当量的活化剂。
将加入活化剂而获得的混合物剧烈搅拌并维持在60℃。在加入后5分钟，取出100毫升的部分溶液并立刻移液至250克碎冰和15毫升冰醋酸构成的混合物上。再加入碘化钾(0.4克)，以淀粉为指示剂用0.1N硫代硫酸钠立刻滴定释放的碘直至首次出现蓝色。用去的硫代硫酸钠的毫升数量便是漂白活化剂的效价。
通常，有机过酸前体是含有一个或多个可进行水解(perhydrolysis)的酰基的化合物。优选的活化剂是那些N-酰基或O-酰基型化合物，它们含有R-CO酰基，其中R优选有1-20个碳原子的烃基或取代烃基。合适的过酸前体的例子包括：
1)如美国专利3,117,148中所揭示的式RCONR1R2的酰基有机酰胺，其中RCO是羧酸酰基，R1是酰基而R2是有机残基。该组中的化合物例子有：
a)N，N-二乙酰苯胺和N-乙酰基苯邻二甲酰亚胺；
b)N-酰基海因，如N，N’-二乙酰基-5，5-二甲基海因；
c)聚酰化亚烷基二胺，如N，N，N’，N’-四乙酰基乙二胺(TAED)和相应的六亚甲基二胺(TAHD)衍生物，如在GB-A-907,356，GB-A-907,357和GB-A-907,358中所公开的；
d)酰化甘脲，如四乙酰基甘脲，如在GB-A-1,246,388、GB-A-1,246,339和GB-A-1247,429中所公开的。
2)酰化磺酰氨，如N-甲基-N-苯甲酰基-薄荷烷氨磺酰和N-苯基-N-乙酰基薄荷烷磺酰氨，如在GB-A-3,1 83,266中所公开的。
3)如在GB-A-836,988、GB-A-963,135和GB-A-1,147,871中所公开的羧酸酯。这种类型化合物的例子包括：乙酸苯酯、乙酸基苯磺酸钠、乙酸三氯乙酯、六乙酸山梨糖醇酯、果糖五乙酸酯、对-硝基苯甲醛二乙酸酯、乙酸异丙烯酯、乙酰基乙酰氧肟酸和乙酰基水杨酸。其他例子是苯酚或取代苯酚与α-氯化的低级脂族羧酸(如氯代乙酰基苯酚和氯代乙酰基水杨酸)形成的酯，如在美国专利3,130,165中所公开的。
4)通式为AcL的羧酸酯，其中Ac是有机羧酸的酰基部分，它具有任意取代的、直链或支链的C6-C20烷基或链烯基部分或被C6-C20烷基取代的芳基部分，而L是离去基团，其共轭酸的pKa为4-13，例如羟苯磺酸酯或羟苯甲酸酯。优选的该类型化合物是这样的化合物，其中
a)Ac是R3-CO，而R3是具有6-20个较佳地6-12个更佳地7-9个碳原子的直链或支链烷基，而且从羰基碳原子延伸出的最长的直链烷基链(包括羰基碳原子)含有5-18个，较佳地5-10个碳原子，R3可任选地被Cl、Br、OCH3或OC2H5所取代(尤其是羰基部分的α位)。该类物质的例子包括：3，5，5-三甲基己酰氧基苯磺酸钠、3，5，5-三甲基己酰氧基苯甲酸钠、2-乙基己酰氧基苯磺酸钠、壬酰氧基苯磺酸钠和辛酰氧基苯磺酸钠，在每个具体化合物中的酰氧基优选是对位取代的；
b)具有式R3(AO)mXA的Ac，其中，R3是直链或支链的烷基或烷芳基(其中在烷基部分含有6-20个较佳地6-15个碳原子)，R5可任选地被Cl、Br、OCH3或OC2H5所取代，AO是氧乙烯或氧丙烯，m为0-100，X是O、NR4或CO-NR4，以及A是CO、CO-CO、R6-CO、CO-R6-CO或CO-NR4-R6-CO其中R4是C1-C4烷基而R6是在亚烷基或亚烯基部分有1-8个碳原子的亚烷基、亚烯基(alkenylene)、亚芳基或亚烷芳基。该类型的漂白活化剂包括式R3(AO)mOCOL的碳酸衍生物、式R3OCO(CH2)2COL的琥珀酸衍生物、式R3OCH2COL的乙醇酸衍生物、式R3OCH2CH2COL的羟基丙酸衍生物、式R3OCOCOL的草酸衍生物、式R3OCOCH＝CHCOL的马来酸和富马酸衍生物、式R3CONR1(CH2)6COL的酰基氨基己酸衍生物、式R3CONR1CH2COL的酰基甘氨酸衍生物和式R3N(R1)CO(CH2)4COL的氨基-6-羰基己酸衍生物。在上述化合物中，m优选为0-10，而R3优选为C6-C12较佳地为C6-C10烷基(当m为0时)和C9-C15烷基(当m不为0时)。离去基团L的定义如上。
5)如美国专利说明书No.3,332,882中所公开的酰基-氰尿酸酯，比如三乙酰基-或三苯甲酰基氰尿酸酯。
6)任意取代的苯甲酸酐或苯二甲酸酐，例如苯甲酸酐、间氯苯甲酸酐和苯二甲酸酐。
在所有的上述化合物中，优选的是1(c)和4(a)类型的有机过酸前体。
当存在时，过酸漂白剂前体的浓度较佳地为总组合物重量的约0.1-10％，更佳地为约0.5-5％，而且一般以漂白剂前体附聚物形式添加。
优选用于本发明的漂白前体附聚物一般含有约5-40％，较佳地约10-30％(重量)的粘合剂或凝结剂。合适的凝结剂包括：聚乙烯吡咯烷酮、分子量为20,000-500,000的聚氧乙烯、分子量为约1000-50,000的聚乙二醇、分子量为4000-20,000的Carbowax、非离子型表面活性剂、脂肪酸，羧甲基纤维素钠、明胶、脂族醇、磷酸盐和多磷酸盐、粘土、硅铝酸盐和聚羧酸酯聚合物。其中，特别优选聚乙二醇，尤其是分子量为约1,000-30,000更佳地为2000-10,000的种类。
从最佳溶解性和pH性能的立场考虑，优选的漂白剂前体附聚物含有约10-75％较佳地约20-60％(重量)过酸漂白剂前体、约5-60％较佳地约5-50％更佳地约10-40％碳酸(氢)盐/酸起泡剂组、约0-20％过硼酸盐和约5-40％较佳地约10-30％凝结剂。
最终的漂白剂前体颗粒最好其粒度为约500-1500微米较佳地约500-1000微米。这从最佳的溶解性和美观角度看是有利的。此外，漂白剂前体附聚物的用量，一般为组合物的约1-20％，较佳地为约5-15％(重量)。
本发明的托牙清洁组合物可以是膏体、片剂、颗粒或粉末形式，尽管片剂型组合物在此处是特别优选的。片剂形式的组合物可以是单层或多层的片剂。
本发明的托牙清洗组合物可添加此类制剂的其他常用成分，尤其是表面活性剂、螯合剂、酶、芳香剂、生清凉剂、抗微生物化合物、染料、甜味剂、片剂用粘合剂和填料、消泡剂如二甲基聚硅氧烷、泡沫稳定剂如脂肪酸糖酯、防腐剂、润滑剂如滑石、硬脂酸镁、细分散的无定形煅制氧化硅等。最终组合物中的游离水含量应小于约1％，尤其是小于约0.5％。
适用于本发明的片剂用粘合剂和填料包括：聚乙烯吡咯烷酮、分子量为20,000-500,000的聚氧乙烯、分子量为约1000-50,000的聚乙二醇、分子量为4000-20,000的Carbowax、非离子型表面活性剂、脂肪酸，羧甲基纤维素钠、明胶、脂族醇、粘土、聚羧酸酯聚合物、碳酸钠、碳酸钙、氢氧化钙、氧化镁、碳酸氢镁、硫酸钠、蛋白质、纤维素醚、纤维素酯、聚乙烯醇、藻酸酯、具有假胶体特性的植物脂肪物质。其中，特别优选聚乙二醇，尤其是分子量为约1,000-30,000更佳地约12,000-30,000的种类。
用于本发明的托牙清洁组合物的表面活性剂，可选自众多与托牙清洁剂其他成分相容的种类，可以是干燥状态或溶液状态。据信这类材料可通过协助组合物中其他成分渗透至牙表面而提供它们的效力。这些物质还协助去除附着在牙齿上的食物碎屑。在组合物中可含有占干组合物重量0.1-5％的干粉末或颗粒状的阴离子表面活性剂如十二烷基硫酸钠、N-月桂酰基肌氨酸钠、乙酸十二烷酯磺酸钠、琥珀酸二辛酯磺酸钠，而且表面活性剂较佳地占组合物的约0.5-4％。
合适的阳离子、非离子和两性离子表面活性剂包括例如：季铵化合物如溴化鲸蜡基三甲基铵，烯化氧如环氧乙烷或氧化丙烯与脂族醇、苯酚、脂族胺或脂肪酸链烷醇酰胺的缩合产物，脂肪酸链烷醇酰胺本身，长链(C8-C22)脂肪酸与多醇或糖形成的酯如甘油单硬脂酸酯或蔗糖单月桂酸酯或山梨糖醇聚氧乙烯单-或二硬脂酸酯，甜菜碱、磺甜菜碱(sulphobetaine)或长链烷基氨基羧酸。
螯合剂通过将金属离子如钙、镁和重金属阳离子保持在溶液中，从而有利于清洗和漂白稳定性。合适的螯合剂包括：三聚磷酸钠、酸性焦磷酸钠、焦磷酸四钠、氨基多羧酸盐如次氮基三乙酸和乙二胺四乙酸及其盐、多膦酸盐和氨基多膦酸盐如羟基乙烷二膦酸、乙二胺四亚甲基膦酸、二亚乙基三胺五亚甲基膦酸以及它们的盐。螯合剂选择并不重要，只是处于干状态和水溶液时它必须与托牙清洁剂的其他成分相容。较佳地，螯合剂占组合物重量的0.1-60％，更佳地为0.5-30％。然而，膦酸型螯合剂较佳地占组合物重量的0.1-1％，更佳地为0.1-0.5％。
适用于此处的酶，以蛋白酶、碱性酶(alkalase)、淀粉酶、脂肪酶、葡聚糖酶(dextranase)、变位酶(mutanase)、葡聚糖酶(glucanase)等为代表。
下面的实施例将进一步描述和阐述本发明范围内的较好实施方案。
实施例I至V
下列是本发明代表性的托牙清洁片剂。百分比按总片剂的重量计算。片剂是通过在冲头和冲模压片机中于约105kPa的压力下冲压颗粒状成分的混合物而制成的。
| I | II | III | IV | V | |
| 苹果酸 | 12 | 10 | 15 | - | 14 |
| 柠檬酸 | - | 10 | - | 15 | - |
| 碳酸钠 | 10 | 8 | 10 | 6 | 10 |
| 氨基磺酸 | 5 | - | - | 3 | 3 |
| PEG 20,000 | - | 3 | 7 | 8 | 5 |
| PVP 40,000 | 6 | 3 | - | - | - |
| 碳酸氢钠 | 22 | 25.2 | 25 | 13.9 | 23 |
| 过硼酸钠一水合物 | 15 | 12 | 16 | 30 | 15 |
| 单过硫酸钾 | 15 | 18 | 13 | - | 14 |
| 煅制氧化硅 | - | 0.3 | 0.1 | 0.1 | - |
| 滑石粉 | 2 | - | - | - | - |
| EDTA | - | - | 1 | - | 3 |
| EDTMP1 | 1 | - | - | 1 | - |
| 香味剂5 | 2 | 1 | 2 | 1 | 2 |
| Abil EM904 | 1 | 1.5 | 5 | 10 | 1 |
| 漂白剂前体附聚物 | 9 | 8 | 10 | 12 | 10 |
| 漂白剂前体附聚物 | I | II | III | IV | V |
| TAED2 | 2 | - | 4 | 5 | 2.5 |
| TMHOS3 | 2 | 3 | - | - | - |
| 氨基磺酸 | 2 | 2 | 2 | 2 | 3.5 |
| 碳酸氢钠 | 0.5 | 0.2 | 0.2 | 0.5 | 2 |
| PEG 6000 | 2.5 | 2 | 2.4 | 2.5 | 1.5 |
| 染料 | - | 0.8 | 1.4 | 2 | 0.5 |
1.乙二胺四亚甲基膦酸
2.四乙酰基乙二胺
3. 3，5，5-三甲基己酰氧基苯磺酸钠
4.十六烷基二甲聚硅氧烷共聚多元醇
5.薄荷类香味剂
在上述的实施例I至V中，片剂的总重量为3克；直径25毫米。
实施例I至V的托牙清洁片剂显示出更佳的抗牙斑性、清洁力和抗菌性，以及优异的附着性和其他物理性能及使用性能。
实施例VI-VIII
下列是本发明的代表性的牙膏/托牙清洁膏。百分比按总组合物的重量计算。
| VI | VII | VIII | |
| 碳酸钙 | 20 | 25 | 15 |
| 甘油 | 10 | 12 | 8 |
| CMC钠 | 3.5 | 3 | 4 |
| 二氧化钛 | 0.7 | 0.5 | 0.6 |
| 对羟苯甲酸甲酯/丁酯 | 0.1 | 0.1 | 0.1 |
| 糖精钠 | 0.3 | 0.4 | 0.2 |
| 香味剂5 | 1 | 1 | 2 |
| Abil EM904 | 1 | 1.5 | 0.5 |
| 三氯生(Trichlosan) | - | 0.5 | - |
| 水 | 加至100 | 加至100 | 加至100 |
实施例VI至VIII的牙膏/托牙清洁膏显示出改良的抗牙斑性、香味和抗菌性，以及优异的清洁性能。
Claims (9)
1.一种牙膏、牙粉、液体洁牙剂、漱口液、托牙清洁剂、口香糖或糖果形式的口腔用组合物，其特征在于，它含有一种或多种选自磨料、粘合剂、保湿剂、表面活性剂、氟离子源、抗牙石剂和甜味剂的口腔用组合物组份，还含有选自式(I)所示烷基-和烷氧基-二甲聚硅氧烷共聚多元醇的二甲聚硅氧烷共聚多元醇：
其中，X选自氢，具有1至约16个碳原子的烷基、烷氧基和酰基；Y选自具有约8至约22个碳原子的烷基和烷氧基；n为约0至约200；m为约l至约40；q为约1至约100；残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000，且x和y为使氧化乙烯∶氧化丙烯的重量比达到约100∶0至约0∶100的数字。
2.如权利要求1所述的组合物，其中二甲聚硅氧烷共聚多元醇选自C12-C20烷基二甲聚硅氧烷共聚多元醇及其混合物。
3.如权利要求1或2所述的组合物，其中二甲聚硅氧烷共聚醇为十六烷基二甲聚硅氧烷共聚多元醇。
4.如权利要求1-3中任一权利要求所述的组合物，其中包含约0.01-25％，较佳地约0.1-5重量％的二甲聚硅氧烷共聚多元醇。
5.如权利要求1-4中任一权利要求所述的组合物，其中包含约10-70重量％的选自下组的牙科磨料：氧化硅，氧化铝，硅铝酸盐，硅酸镁和硅酸锆，正磷酸钙，焦磷酸钙，偏磷酸钙及多磷酸钙，碳酸钙和碳酸镁，不溶性偏磷酸盐和热固性聚合树脂。
6.如权利要求1-5中任一权利要求所述的组合物，其中包含足能提供约50-3500ppm的氟离子的氟离子源量。
7.如权利要求1-6中任一权利要求所述的组合物，其中包含约0.1-1重量％粘合剂。
8.二甲聚硅氧烷共聚多元醇在口腔用组合物中作为抗牙斑剂的用途，其特征在于，二甲聚硅氧烷共聚多元醇选自式(I)所示烷基-和烷氧基-二甲聚硅氧烷共聚多元醇：
其中，X选自氢，具有1至约16个碳原子的烷基、烷氧基和酰基；Y选自具有约8至约22个碳原子的烷基和烷氧基；n为约0至约200；m为约1至约40；q为约1至约100；残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000，且x和y为使氧化乙烯∶氧化丙烯的重量比达到约100∶0至约0∶100的数字。
9.如权利要求8所述用途，其特征在于，该口腔用组合物是托牙清洁组合物。
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| GBGB9425941.3A GB9425941D0 (en) | 1994-12-22 | 1994-12-22 | Oral composition |
| GB9425941.3 | 1994-12-22 |
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| EP (1) | EP0793478A4 (zh) |
| JP (1) | JPH10511349A (zh) |
| KR (1) | KR100246832B1 (zh) |
| CN (1) | CN1088578C (zh) |
| AU (1) | AU4514096A (zh) |
| BR (1) | BR9510307A (zh) |
| CA (1) | CA2208364C (zh) |
| CZ (1) | CZ292313B6 (zh) |
| GB (1) | GB9425941D0 (zh) |
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| PL (1) | PL320866A1 (zh) |
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| TR (1) | TR199501645A2 (zh) |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106139204A (zh) * | 2014-08-22 | 2016-11-23 | 穗晔实业股份有限公司 | 具有臭味净化功能的水性溶液 |
| CN107519026A (zh) * | 2017-10-10 | 2017-12-29 | 广州立白企业集团有限公司 | 一种具有去渍及清新口气的牙粉及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6294154B1 (en) | 1994-12-22 | 2001-09-25 | Procter And Gamble Company | Oral compositions containing dimethicone copolyols |
| DE19646985A1 (de) * | 1996-11-14 | 1998-06-04 | Michael Dr Weichsel | Geschmacksverbesserung bei Zahnregulierungsapparaten |
| ATE391467T1 (de) | 1997-01-16 | 2008-04-15 | Procter & Gamble | Verfahren zur behandlung von gebiss-prothesen |
| KR100478211B1 (ko) * | 1997-10-01 | 2005-08-11 | 애경산업(주) | 미백치약조성물 |
| US6648983B1 (en) * | 1998-11-10 | 2003-11-18 | The Procter & Gamble Company | Process of cleaning enamel surfaces |
| US6685921B2 (en) | 2000-10-25 | 2004-02-03 | The Procter & Gamble Company | Dental care compositions |
| KR101168380B1 (ko) | 2003-12-11 | 2012-07-25 | 코닌클리케 필립스 일렉트로닉스 엔.브이. | 구강 조성물을 위한 펌핑 시스템 |
| GB0513367D0 (en) * | 2005-06-30 | 2005-08-03 | Glaxo Group Ltd | Novel composition |
| EP2458986B1 (en) * | 2009-07-27 | 2016-08-31 | Dow Global Technologies LLC | Synergistic antimicrobial composition |
| JP6367343B2 (ja) | 2013-10-28 | 2018-08-01 | ザ プロクター アンド ギャンブル カンパニー | レオロジー変性剤の後期添加 |
| WO2019032795A1 (en) | 2017-08-09 | 2019-02-14 | The Procter & Gamble Company | APTAMERS FOR ORAL CARE COMPOSITIONS |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1034782A (en) * | 1962-01-24 | 1966-07-06 | Union Carbide Corp | Organosilicon compositions |
| US4950479A (en) * | 1986-11-06 | 1990-08-21 | Hill Ira D | Method of interrupting the formation of plaque |
| US5078998A (en) * | 1985-08-02 | 1992-01-07 | Bevan Michael J | Hybrid ligand directed to activation of cytotoxic effector T lymphocytes and target associated antigen |
| US5032387A (en) * | 1986-11-06 | 1991-07-16 | Princeton Pharmaceutical Inc. | Dental and oral hygiene preparations |
| US5078988A (en) * | 1988-11-28 | 1992-01-07 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Dentrifrices including modified aminoalkyl silicones |
| US5284648A (en) * | 1989-03-17 | 1994-02-08 | White Robert D | Alcohol-free, oral rinse and pre-rinse emulsions method of prepration and method of use |
| US5162378A (en) * | 1990-04-20 | 1992-11-10 | Revlon Consumer Products Corporation | Silicone containing water-in-oil microemulsions having increased salt content |
| FR2701845B1 (fr) * | 1993-02-23 | 1995-04-07 | Oreal | Emulsion eau-dans-huile à usage cosmétique ou pharmaceutique. |
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- 1995-12-12 RU RU97112452/14A patent/RU2163480C2/ru not_active IP Right Cessation
- 1995-12-12 CA CA002208364A patent/CA2208364C/en not_active Expired - Fee Related
- 1995-12-12 CN CN95196900A patent/CN1088578C/zh not_active Expired - Fee Related
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- 1995-12-12 WO PCT/US1995/016051 patent/WO1996019191A1/en active IP Right Grant
- 1995-12-12 KR KR1019970704212A patent/KR100246832B1/ko not_active IP Right Cessation
- 1995-12-12 CZ CZ19971886A patent/CZ292313B6/cs not_active IP Right Cessation
- 1995-12-12 SK SK828-97A patent/SK82897A3/sk unknown
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106139204A (zh) * | 2014-08-22 | 2016-11-23 | 穗晔实业股份有限公司 | 具有臭味净化功能的水性溶液 |
| CN107519026A (zh) * | 2017-10-10 | 2017-12-29 | 广州立白企业集团有限公司 | 一种具有去渍及清新口气的牙粉及其制备方法 |
| CN107519026B (zh) * | 2017-10-10 | 2020-08-04 | 广州立白企业集团有限公司 | 一种具有去渍及清新口气的牙粉及其制备方法 |
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| Publication number | Publication date |
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| BR9510307A (pt) | 1997-11-11 |
| KR100246832B1 (ko) | 2000-04-01 |
| MX9704721A (es) | 1997-10-31 |
| AU4514096A (en) | 1996-07-10 |
| HUT77713A (hu) | 1998-07-28 |
| CA2208364A1 (en) | 1996-06-27 |
| CN1088578C (zh) | 2002-08-07 |
| CA2208364C (en) | 2001-11-06 |
| CZ188697A3 (en) | 1997-11-12 |
| HU220794B1 (hu) | 2002-05-28 |
| WO1996019191A1 (en) | 1996-06-27 |
| CZ292313B6 (cs) | 2003-09-17 |
| TR199501645A3 (zh) | 1996-07-21 |
| EP0793478A1 (en) | 1997-09-10 |
| TR199501645A2 (tr) | 1996-07-21 |
| SK82897A3 (en) | 1998-01-14 |
| JPH10511349A (ja) | 1998-11-04 |
| RU2163480C2 (ru) | 2001-02-27 |
| PL320866A1 (en) | 1997-11-10 |
| GB9425941D0 (en) | 1995-02-22 |
| EP0793478A4 (en) | 2005-10-12 |
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