US2955985A - Dentifrice compositions - Google Patents
Dentifrice compositions Download PDFInfo
- Publication number
- US2955985A US2955985A US595133A US59513356A US2955985A US 2955985 A US2955985 A US 2955985A US 595133 A US595133 A US 595133A US 59513356 A US59513356 A US 59513356A US 2955985 A US2955985 A US 2955985A
- Authority
- US
- United States
- Prior art keywords
- dentifrice
- phosphate
- water
- sodium
- paste
- 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.)
- Expired - Lifetime
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- 239000000551 dentifrice Substances 0.000 title claims description 38
- 239000000203 mixture Substances 0.000 title description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 24
- 239000010452 phosphate Substances 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
- 235000021317 phosphate Nutrition 0.000 description 23
- -1 fluoroalkyl phosphates Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000006072 paste Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000606 toothpaste Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 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 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000005498 polishing Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229940034610 toothpaste Drugs 0.000 description 6
- 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 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 239000001506 calcium phosphate Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 229940105329 carboxymethylcellulose Drugs 0.000 description 4
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 4
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 4
- 229940038472 dicalcium phosphate Drugs 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- 239000003765 sweetening agent Substances 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000000271 synthetic detergent Substances 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- WGIMXKDCVCTHGW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCO WGIMXKDCVCTHGW-UHFFFAOYSA-N 0.000 description 1
- PWVUXRBUUYZMKM-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCO PWVUXRBUUYZMKM-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
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 101100203600 Caenorhabditis elegans sor-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 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
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 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
- 229940043256 calcium pyrophosphate Drugs 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- 229940031768 diglycol stearate Drugs 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000004408 titanium dioxide 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
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
- A61K8/70—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
-
- 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
- This invention relates to a dentifrice, and more particularly to a dentifrice in paste, powder or liquid form, which tends to reduce the normal susceptibility of the teeth to attack from acid.
- the present invention is based upon the discovery that a dentifrice containing as an essential ingredient or comwherein n is an integer from 1 to 5, inclusive, x is an integer from 1 to 3, inclusive, y equals 3x, and'M is hydrogen, an alkali-metal or an ammonium ion.
- the preferred esters are those in which n is an integer from 2 to 4, inclusive, x is 1, y is 2; and M is an alka i-metal or an ammonium ion, desirably the latter.
- the ammonium salt of 1,1,7-trihydroperfiuoroheptyl phosphate has provided excellent results.
- the contemplated alkalimetals are lithium, potassium and sodium, preferably the latter.
- esters of phosphoric acid and their water-soluble salts defined above will be referred to in this specification as the fluoroalkyl phosphates.
- fluoroalkylphosphates contemplated for incorpor ation into the dentifrices of the invention fall withinthe following three types.
- n and M have the same definitions as above.
- the water-soluble salts of the monoesters, and particularly their ammonium salts are pre ferred because of their greater water-solubility, whereas the triesters have substantially reduced solubility in water and are therefore not the preferred esters for use in the invention.
- the triesters, as a class, frequently are liquids and therefore are not as suitable in the preparation of dry powder dentifrices.
- esters and their salts and their methods of preparation are described in U.S. Patent No. 2,597,702 of A. F. Benning. It is intended to incorporate by reference the entire disclosure of the patent into this specification. These esters may be produced by several methods, including the reaction between an appropriate fluorinated alk anol and phosphorus pentoxide or phosphorus oxy- I chloride.
- phosphates contemplated for employment in the'dentifrices of the invention are: l,1,7-trihydroperfluoroheptyl phosphate" and its ammonium salt; l,1,3-trihydroperfluoropropyl phosphate and phosphate, etc., and mixtures of them.
- the ammonium ion in the salts may be replaced with an alkali-metal ion to form the sodium, potassium or lithium salts.
- the concentration of the selected fiuoroalkyl phosphate or its salts in the dentifrice may Vary, best results are obtained where the selectedphosphatecon-f stitutes betweenabout' 0.05% and '2;0%, andipre ferab'ly" between 1.0% and 1.8%, by weight of the total dentifrice composition. Below 0.05% the phosphate may be ineffective, and above 2.0% it may not be utilized efiiciently.
- the dentifrice is a paste or powder it is desirable to incorporate into the dentifrice a solid polishing agent, such as dicalcium phosphate, calcium pyrophosphate', tri calcium phosphate or powdered chalk (calcium carbonate), etc.
- a solid polishing agent such as dicalcium phosphate, calcium pyrophosphate', tri calcium phosphate or powdered chalk (calcium carbonate), etc.
- Non-calcium-containing polishingagents such as aluminum oxide, titanium dioxide, ground pumice, 1
- powdered nylon, etc. may be employed.
- the dentifrice can contain as optional ingredients a soap or synthetic detergent as a surface tension depressant.
- a soap or synthetic detergent as a surface tension depressant.
- Soaps of high molecular weight fatty acids including, for example, -sodium and potassium soaps of myristic, stearic and palmitic acids and the fatty acid mixtures of palm oil and coconut oil, as well as diglycol laurate, diglycol stearate and glyco-. stearine, can be employed.
- Typical synthetic detergents include the alkyl sulfates and sulfonates having alkyl' groups of from about 8 to'about 18 carbon atoms, such as sodium lauryl sulfate, the sulfated fatty alcohols derived from coconut oil and palm oil, sodium cetyl sulfate," sulfated sperm oil fatty alcohols and sodium oleyl sulfate, sulfated glycerides, such as oleyl, stearic, palrnitic and ricinoleic glycerides, usually in the form of mixed glycerides and sulfonated hydrocarbons having from 8 to 20 carbon atoms, such as sulfonated decanes, dodccan e s. andoctadecanes. Particularly good results are obtained:
- Tweens such as Tween 20 which is the polyoxyethylene derivative of sorbitan
- Atlas G-2160 which is the polyoxyethylene derivative of mannitan.
- Drucals such as sodium lauryl isethionate, or sodium mixed alkyl isethionates.
- a dentifrice which may be present include flavoring materials, such as the flavoring oils (peppermint oil, etc.) sweeteners, such as sucrose, glueose, saccharin and sodium cyclamate, and harmless coloring materials, in proportions to give any desired taste or flavor or other effect.
- flavoring oils peppermint oil, etc.
- sweeteners such as sucrose, glueose, saccharin and sodium cyclamate
- harmless coloring materials in proportions to give any desired taste or flavor or other effect.
- the dentifrice is in the form of a paste, and in this event it will contain a carrier and softener and a binder in amounts to give the dentifrice a smooth texture and good flowability.
- a carrier and softener and a binder in amounts to give the dentifrice a smooth texture and good flowability.
- Glycerin and sorbitol are preferred humectants, carriers and softeners, but syrup, glucose and invert sugars and honey can also be employed.
- binders there can be used carboxymethylcellulose, gum tragacanth, sodium alginate, Irish moss, gum acacia, pectin, etc.
- the pastes may be either of the aqueous type, containing substantial amounts of water (above 18%), or of the relatively anhydrous type, containing less than 5% water. Formulations are given below for both types.
- the dentifrices of the invention may be in the form of powders or liquids.
- the main difference between a paste and powder is that the latter contains little or no water and usually no binder or softener.
- a liquid usually differs from a paste in that it is more fluid and it contains no solid polishing agent.
- Aqueous tooth paste Parts by weight Relatively anhydrous tooth paste Parts by weight Fluoroalkyl phosphate 0.05 to 2.0 Water to 4.5 Binder 0.3 to 1.2 Polishing agent 45 to 70 Humectant 25 to 45 Detergent 0 to 2 Sweetener 0.03 to 0.10 Flavoring oils 0.9 to 1.2
- Fluoroalkyl phosphate 0.05 to 2.0 Water 60.1 to 92 Detergent 1.5 to 5 Softener 5 to 30 Binder or suspending agent 0.5 to 1.5 Flavoring agent 0.85 to 1.2 Sweetener 0.1 to 0.2
- EXAMPLE IV The following is an example of a tooth paste formulation which is relatively anhydrous, i.e., having less than 5% water:
- n is an integer from 1 to 5, inclusive
- 2 is an 6 integer from 1 to 3, inclusive
- y equals 3x
- M is a member selected from the class consisting of hydrogen, an alkali-metal ion and an ammonium ion.
- a dentifrice comprising a dentifrice vehicle and at least about 0.05% by weight of a fluoroalkyl phosphate of the formula:
- n is an integer from 1 to 5, inclusive
- M is a member selected from the class consisting of hydrogen, an alkali-metal ion and an ammonium ion.
- a dentifrice is accordance with claim 1, in which the vehicle is a paste.
- fluoroalkyl phosphate is' monoammonium-1,1,7-trihydroperfluoroheptyl phosphate.
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Description
Patented Oct. 11, 1960 iiee% DENTIFRICE coMrosrrroNs Martin Kuna, Westfield, NJ., assignor to Bristol-Myers Company, New York, N.Y., a corporation of Delaware No Drawing. Filed July 2, 1956, Ser. No. 595,133
Claims. (Cl. 167-93) This invention relates to a dentifrice, and more particularly to a dentifrice in paste, powder or liquid form, which tends to reduce the normal susceptibility of the teeth to attack from acid.
It is generally accepted that dental caries result at least partially from the acids formed by microorganisms in the mouth in the course of their metabolism. These acids, when in contact with the teeth, attack the enamel of the teeth, dissolving the enamel, and result in tooth decay. A considerable amount of research effort has been devoted to find a means of protecting the teeth against the attack of these acids. Numerous proposals have been advanced to solve the problem. Those skilled in the dentifrice art are familiar with these proposals. One proposal was the incorporation of a basic ammonium salt in a dentifrice. These were known as the ammoniated dentifrices. Another was the use of chlorophyll in a dentifrice. Another was the incorporation of a socalled anti-enzyme, such as sodium lauryl sulfate, into a dentifrice. While some of these proposals have given indications of being helpful, none of them has provided satisfactory protection of the teeth against the ravages of acids, such as are formed in the mouth. I
It is an object of the present invention to provide an improved dentifrice having the property of reducing the normal susceptibility of the teeth to acid attack.
It is another object of the present invention to incorporate in a dentifrice an agent affording protection to the teeth enamel against acid attack and resisting calculus formation on the teeth.
Other objects will be apparent to those skilled in the 7 art from reading the description which follows.
The present invention is based upon the discovery that a dentifrice containing as an essential ingredient or comwherein n is an integer from 1 to 5, inclusive, x is an integer from 1 to 3, inclusive, y equals 3x, and'M is hydrogen, an alkali-metal or an ammonium ion. The preferred esters are those in which n is an integer from 2 to 4, inclusive, x is 1, y is 2; and M is an alka i-metal or an ammonium ion, desirably the latter. The ammonium salt of 1,1,7-trihydroperfiuoroheptyl phosphate has provided excellent results. The contemplated alkalimetals are lithium, potassium and sodium, preferably the latter.
The esters of phosphoric acid and their water-soluble salts defined above will be referred to in this specification as the fluoroalkyl phosphates.
2 The fluoroalkylphosphates contemplated for incorpor ation into the dentifrices of the invention fall withinthe following three types.
H CF CH OPO(OM -(monoester) H (CF 2 CH Ol P0 OM )--(diester) [H (CF CH O] PO(triester) wherein n and M have the same definitions as above. As indicated above, the water-soluble salts of the monoesters, and particularly their ammonium salts, are pre ferred because of their greater water-solubility, whereas the triesters have substantially reduced solubility in water and are therefore not the preferred esters for use in the invention. The triesters, as a class, frequently are liquids and therefore are not as suitable in the preparation of dry powder dentifrices.
The selected fluoroalkyl phosphates and their watersoluble salts described above are known chemical compounds and per se do not constitute a part of this invention. These esters and their salts and their methods of preparation are described in U.S. Patent No. 2,597,702 of A. F. Benning. It is intended to incorporate by reference the entire disclosure of the patent into this specification. These esters may be produced by several methods, including the reaction between an appropriate fluorinated alk anol and phosphorus pentoxide or phosphorus oxy- I chloride.
Among the preferred fluoroa'lkyl, phosphates contemplated for employment in the'dentifrices of the invention are: l,1,7-trihydroperfluoroheptyl phosphate" and its ammonium salt; l,1,3-trihydroperfluoropropyl phosphate and phosphate, etc., and mixtures of them. The ammonium ion in the salts may be replaced with an alkali-metal ion to form the sodium, potassium or lithium salts.
While the concentration of the selected fiuoroalkyl phosphate or its salts in the dentifrice may Vary, best results are obtained where the selectedphosphatecon-f stitutes betweenabout' 0.05% and '2;0%, andipre ferab'ly" between 1.0% and 1.8%, by weight of the total dentifrice composition. Below 0.05% the phosphate may be ineffective, and above 2.0% it may not be utilized efiiciently.
Where the dentifrice is a paste or powder it is desirable to incorporate into the dentifrice a solid polishing agent, such as dicalcium phosphate, calcium pyrophosphate', tri calcium phosphate or powdered chalk (calcium carbonate), etc. Non-calcium-containing polishingagents, such as aluminum oxide, titanium dioxide, ground pumice, 1
powdered nylon, etc., may be employed.
In addition to the selected fiuoroalkyl phosphate and polishing agent- (when desired), the dentifrice can contain as optional ingredients a soap or synthetic detergent as a surface tension depressant. Soaps of high molecular weight fatty acids, including, for example, -sodium and potassium soaps of myristic, stearic and palmitic acids and the fatty acid mixtures of palm oil and coconut oil, as well as diglycol laurate, diglycol stearate and glyco-. stearine, can be employed. Typical synthetic detergents include the alkyl sulfates and sulfonates having alkyl' groups of from about 8 to'about 18 carbon atoms, such as sodium lauryl sulfate, the sulfated fatty alcohols derived from coconut oil and palm oil, sodium cetyl sulfate," sulfated sperm oil fatty alcohols and sodium oleyl sulfate, sulfated glycerides, such as oleyl, stearic, palrnitic and ricinoleic glycerides, usually in the form of mixed glycerides and sulfonated hydrocarbons having from 8 to 20 carbon atoms, such as sulfonated decanes, dodccan e s. andoctadecanes. Particularly good results are obtained:
diammonium 1,1,9 trihydroperfiuorononyl' with Tweens, such as Tween 20 which is the polyoxyethylene derivative of sorbitan, and Atlas G-2160 which is the polyoxyethylene derivative of mannitan. Another type is the Drucals, such as sodium lauryl isethionate, or sodium mixed alkyl isethionates.
Other optional conventional components of a dentifrice which may be present include flavoring materials, such as the flavoring oils (peppermint oil, etc.) sweeteners, such as sucrose, glueose, saccharin and sodium cyclamate, and harmless coloring materials, in proportions to give any desired taste or flavor or other effect.
In a preferred embodiment of the invention, the dentifrice is in the form of a paste, and in this event it will contain a carrier and softener and a binder in amounts to give the dentifrice a smooth texture and good flowability. Glycerin and sorbitol are preferred humectants, carriers and softeners, but syrup, glucose and invert sugars and honey can also be employed. As binders there can be used carboxymethylcellulose, gum tragacanth, sodium alginate, Irish moss, gum acacia, pectin, etc. Those skilled in the dentifrice art will know other carriers, softeners and binders. The pastes may be either of the aqueous type, containing substantial amounts of water (above 18%), or of the relatively anhydrous type, containing less than 5% water. Formulations are given below for both types.
In addition to pastes, the dentifrices of the invention may be in the form of powders or liquids. The main difference between a paste and powder is that the latter contains little or no water and usually no binder or softener. A liquid usually differs from a paste in that it is more fluid and it contains no solid polishing agent.
The following are general formulations of tooth pastes, powders and liquids of the type contemplated according to the present invention (parts are expressed in terms of parts by weight):
Aqueous tooth paste Parts by weight Relatively anhydrous tooth paste Parts by weight Fluoroalkyl phosphate 0.05 to 2.0 Water to 4.5 Binder 0.3 to 1.2 Polishing agent 45 to 70 Humectant 25 to 45 Detergent 0 to 2 Sweetener 0.03 to 0.10 Flavoring oils 0.9 to 1.2
Powder Parts by weight Fluoroalkyl phosphate 0.05 to 2.0 Polishing agent 93.6 to 98 Detergent 1 to 3 Flavoring oils 0.85 to 1.2 Sweetener 0.1 to 0.2
Liquid Parts by weight Fluoroalkyl phosphate 0.05 to 2.0 Water 60.1 to 92 Detergent 1.5 to 5 Softener 5 to 30 Binder or suspending agent 0.5 to 1.5 Flavoring agent 0.85 to 1.2 Sweetener 0.1 to 0.2
EXAMPLE I The following is an example of a tooth paste formulation:
Ingredient: Parts by weight Monoammonium 1,1,7-trihydroperfluoroheptyl phosphate 1.0 Deionized water 22.9 Soluble saccharin 0.15 Carboxymethylcellulose (HV-l20) 1.0 Dicalcium phosphate 49.0 Sorbitol 23.05 Sodium lauryl sulfate 1.8 Flavoring oils 1.10
EXAMPLE II The following is an example of a series of tooth paste formulations:
Ingredient A B Ammonium di- (1, 1, 5-trihydroperfluoramyl) phosphate 1. 80 Diammonium 1 ,1, Q-trihydroperfluorononyl phosphate 1. 80 Deionized water 22. 90 22. 90 Soluble saecharin 0.15 0.15 Carboxymethylcellulose (H 20 1.0 1.0 Dicalcium phosphate 50.0 50.0
Sorbitol 23.05 23.05 Flavoring oils 1. 10 1.10
EXAMPLE III The following is an example of a series of tooth paste formulations:
Ingredient A l B C l D Monoammonium 1,1,7-trihydroperfluoroheptyl phosphate 1. 8 0. 9 1.0 1.0 22. 90 22. 90 22.8 22. 5 Soluble saecharin 0.15 0.15 0.15 0.15 Garboxymethylcellulose (EV-120)-.. 1.0 1.0 1.0 1.0 Diealcium phosphate 50.0 50.0 49. 0 49. 65 Sorbitol 23.05 23.05 23.05 23.05
Drucal (CHD)-(a mixture of sodium lauryl isethionate and sodium myristyl isethionate) 0.9 Sodium lauryl sulfate 1.0 1. 50 Flavoring oils 1. 1 1.1 1.1 1.1
EXAMPLE IV The following is an example of a tooth paste formulation which is relatively anhydrous, i.e., having less than 5% water:
Ingredient: Parts by weight Monoammonium 1,1,7 trihydroperfluoroheptyl phosphate 1.55 Water, deionized 4.35 Glycerin U.S.P. 41.0
Saccharin, soluble U.S.P. 0.05 Carbomethylcellulose (HV-120) 0.50 Dicalcium phosphate 50.85 Sodium lauryl sulfate 1.80 Flavoring oils 1.0
5 EXAMPLE v The following is an example of a series of tooth powder formulations:
Ingredient A B Monoamlmonium-l,1,7-tr1hydroperfluoroheptyl ate EXAMPLE VI The following is an example of a series of liquid dentifrice formulations:
Ingredient A B Monoammonium-l,1,7-trihydroperfluorohepty1 phosphate 1. 5 1. 5 Sorbitol 20. O 15. Water 75.0 79. Carboxymethylce llulose 1. 0 1. O Soluble saccharin 0. 15 0.15 Polyoxyethylene sor 1. 5 1. 5 Flavoring oils 0. 85 1.0
[H(CF ,,CH O],;PO(OM) wherein n is an integer from 1 to 5, inclusive, 2: is an 6 integer from 1 to 3, inclusive, y equals 3x, and M is a member selected from the class consisting of hydrogen, an alkali-metal ion and an ammonium ion.
2. A dentifrice comprising a dentifrice vehicle and at least about 0.05% by weight of a fluoroalkyl phosphate of the formula:
H(CF CH OPO(OM) wherein n is an integer from 1 to 5, inclusive, and M is a member selected from the class consisting of hydrogen, an alkali-metal ion and an ammonium ion.
3. A dentifrice is accordance with claim 1, in which the vehicle is a paste.
4. A dentifrice in accordance with claim 1, in which the vehicle is a powder.
5. A dentifrice in accordance with claim 1, in which the vehicle is a liquid.
6. A dentifrice in accordance with claim 1, which also contains a polishing agent.
7. A dentifrice in accordance with claim 1, which also contains a surface tension depressant.
8. A dentifrice in accordance with claim 7, wherein the surface tension depressant is a synthetic detergent.
9. A dentifrice in accordance with claim 1, which also contains a binder.
10. A dentifrice in accordance with claim 1, wherein the fluoroalkyl phosphate is' monoammonium-1,1,7-trihydroperfluoroheptyl phosphate.
References Cited in the file of this patent UNITED STATES PATENTS 2,692,264 Wojcik Oct. 19, 1954 FOREIGN PATENTS 158,717 Australia Sept. 9, 1954 OTHER REFERENCES Shourie et al: J. Dent. Res., August 1950, pp. 529-533.
Claims (1)
1. A DENTIFRICE COMPRISING A DENTIFRICE VEHICLE AND AT LEAST ABOUT 0.05% BY WEIGHT OF A FLUOROALKYL PHOSPHATE OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US595133A US2955985A (en) | 1956-06-18 | 1956-07-02 | Dentifrice compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US591808A US2955984A (en) | 1956-06-18 | 1956-06-18 | Dentifrices |
| US595133A US2955985A (en) | 1956-06-18 | 1956-07-02 | Dentifrice compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2955985A true US2955985A (en) | 1960-10-11 |
Family
ID=27081256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US595133A Expired - Lifetime US2955985A (en) | 1956-06-18 | 1956-07-02 | Dentifrice compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2955985A (en) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3152181A (en) * | 1961-01-18 | 1964-10-06 | Us Vitamin Pharm Corp | Alkoxypropylene biguanides |
| US3183230A (en) * | 1961-01-13 | 1965-05-11 | Us Vitamin Pharm Corp | Haloaralkyl biguanides |
| US3308208A (en) * | 1964-05-04 | 1967-03-07 | Douglas Aircraft Co Inc | Polyfluorinated phosphate esters |
| US3308207A (en) * | 1964-05-04 | 1967-03-07 | Douglas Aircraft Co Inc | Polyfluorinated phosphate esters |
| US3939261A (en) * | 1974-08-30 | 1976-02-17 | Colgate-Palmolive Company | Flavored dentifrice |
| WO1979000455A1 (en) * | 1977-12-29 | 1979-07-26 | Minnesota Mining & Mfg | Composition and method for inhibiting plaque formation |
| WO1979000456A1 (en) * | 1977-12-29 | 1979-07-26 | Minnesota Mining & Mfg | Compositions and methods for inhibiting plaque formation |
| US4243658A (en) * | 1979-04-02 | 1981-01-06 | Minnesota Mining And Manufacturing Company | Compositions and methods for reducing elution of therapeutic agents from teeth |
| US4304766A (en) * | 1979-04-02 | 1981-12-08 | Minnesota Mining And Manufacturing Company | Compositions for reducing elution of therapeutic agents from teeth |
| US4353892A (en) * | 1981-08-13 | 1982-10-12 | Forsyth Dental Infirmary For Children | Fluoride preparations containing surface-active agents |
| US4366146A (en) * | 1980-08-11 | 1982-12-28 | Minnesota Mining & Manufacturing Co. | Compositions and method for reducing elution of therapeutic agents from teeth |
| US4428930A (en) | 1981-09-18 | 1984-01-31 | Minnesota Mining And Manufacturing Company | Compositions and method for reducing elution of therapeutic agents from teeth |
| US4470964A (en) * | 1981-09-18 | 1984-09-11 | Minnesota Minning And Manufacturing Company | Composition and method for reducing elution of therapeutic agents from teeth |
| US4485090A (en) * | 1981-09-18 | 1984-11-27 | Minnesota Mining And Manufacturing Company | Composition and method for reducing elution of therapeutic agents from teeth |
| USRE31787E (en) * | 1979-04-02 | 1985-01-01 | Minnesota Mining And Manufacturing Company | Compositions for reducing elution of therapeutic agents from teeth |
| US4510127A (en) * | 1981-09-18 | 1985-04-09 | Minnesota Mining And Manufacturing Company | Compositions and method for reducing elution of therapeutic agents from teeth |
| WO2014000982A1 (en) * | 2012-06-26 | 2014-01-03 | Unilever Plc | Oral care compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692264A (en) * | 1950-05-02 | 1954-10-19 | Hooker Electrochemical Co | Quaternary ammonium containing compounds containing fluoroalkyl monocyclic aromatic hydrocarbon groups |
-
1956
- 1956-07-02 US US595133A patent/US2955985A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692264A (en) * | 1950-05-02 | 1954-10-19 | Hooker Electrochemical Co | Quaternary ammonium containing compounds containing fluoroalkyl monocyclic aromatic hydrocarbon groups |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183230A (en) * | 1961-01-13 | 1965-05-11 | Us Vitamin Pharm Corp | Haloaralkyl biguanides |
| US3152181A (en) * | 1961-01-18 | 1964-10-06 | Us Vitamin Pharm Corp | Alkoxypropylene biguanides |
| US3308208A (en) * | 1964-05-04 | 1967-03-07 | Douglas Aircraft Co Inc | Polyfluorinated phosphate esters |
| US3308207A (en) * | 1964-05-04 | 1967-03-07 | Douglas Aircraft Co Inc | Polyfluorinated phosphate esters |
| US3939261A (en) * | 1974-08-30 | 1976-02-17 | Colgate-Palmolive Company | Flavored dentifrice |
| US4071615A (en) * | 1974-08-30 | 1978-01-31 | Colgate Palmolive Company | Flavored dentifrice |
| US4170636A (en) * | 1977-12-29 | 1979-10-09 | Minnesota Mining And Manufacturing Company | Composition and method for inhibiting plaque formation |
| WO1979000456A1 (en) * | 1977-12-29 | 1979-07-26 | Minnesota Mining & Mfg | Compositions and methods for inhibiting plaque formation |
| WO1979000455A1 (en) * | 1977-12-29 | 1979-07-26 | Minnesota Mining & Mfg | Composition and method for inhibiting plaque formation |
| US4243658A (en) * | 1979-04-02 | 1981-01-06 | Minnesota Mining And Manufacturing Company | Compositions and methods for reducing elution of therapeutic agents from teeth |
| US4304766A (en) * | 1979-04-02 | 1981-12-08 | Minnesota Mining And Manufacturing Company | Compositions for reducing elution of therapeutic agents from teeth |
| USRE31787E (en) * | 1979-04-02 | 1985-01-01 | Minnesota Mining And Manufacturing Company | Compositions for reducing elution of therapeutic agents from teeth |
| US4366146A (en) * | 1980-08-11 | 1982-12-28 | Minnesota Mining & Manufacturing Co. | Compositions and method for reducing elution of therapeutic agents from teeth |
| US4353892A (en) * | 1981-08-13 | 1982-10-12 | Forsyth Dental Infirmary For Children | Fluoride preparations containing surface-active agents |
| US4428930A (en) | 1981-09-18 | 1984-01-31 | Minnesota Mining And Manufacturing Company | Compositions and method for reducing elution of therapeutic agents from teeth |
| US4470964A (en) * | 1981-09-18 | 1984-09-11 | Minnesota Minning And Manufacturing Company | Composition and method for reducing elution of therapeutic agents from teeth |
| US4485090A (en) * | 1981-09-18 | 1984-11-27 | Minnesota Mining And Manufacturing Company | Composition and method for reducing elution of therapeutic agents from teeth |
| US4510127A (en) * | 1981-09-18 | 1985-04-09 | Minnesota Mining And Manufacturing Company | Compositions and method for reducing elution of therapeutic agents from teeth |
| WO2014000982A1 (en) * | 2012-06-26 | 2014-01-03 | Unilever Plc | Oral care compositions |
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