GB2190288A - Stabilized amine fluoride dental cream - Google Patents
Stabilized amine fluoride dental cream Download PDFInfo
- Publication number
- GB2190288A GB2190288A GB08711302A GB8711302A GB2190288A GB 2190288 A GB2190288 A GB 2190288A GB 08711302 A GB08711302 A GB 08711302A GB 8711302 A GB8711302 A GB 8711302A GB 2190288 A GB2190288 A GB 2190288A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dental cream
- weight
- fluoride
- polyethylene glycol
- present
- 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
- 239000006071 cream Substances 0.000 title claims description 71
- ZVVSSOQAYNYNPP-UHFFFAOYSA-N olaflur Chemical compound F.F.CCCCCCCCCCCCCCCCCCN(CCO)CCCN(CCO)CCO ZVVSSOQAYNYNPP-UHFFFAOYSA-N 0.000 title claims description 22
- 229960001245 olaflur Drugs 0.000 title claims description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims description 20
- 229920001223 polyethylene glycol Polymers 0.000 claims description 20
- 235000011187 glycerol Nutrition 0.000 claims description 19
- 239000003906 humectant Substances 0.000 claims description 17
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 238000005498 polishing Methods 0.000 claims description 15
- 239000000600 sorbitol Substances 0.000 claims description 15
- 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 claims description 14
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 14
- 238000005191 phase separation Methods 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 229940091249 fluoride supplement Drugs 0.000 claims description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 11
- 239000003349 gelling agent Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 8
- AQMNWCRSESPIJM-UHFFFAOYSA-M sodium metaphosphate Chemical group [Na+].[O-]P(=O)=O AQMNWCRSESPIJM-UHFFFAOYSA-M 0.000 claims description 8
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000011775 sodium fluoride Substances 0.000 claims description 4
- 235000013024 sodium fluoride Nutrition 0.000 claims description 4
- 229960004711 sodium monofluorophosphate Drugs 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 238000010348 incorporation Methods 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 229910001506 inorganic fluoride Inorganic materials 0.000 claims 2
- 239000000306 component Substances 0.000 claims 1
- -1 amine hydrofluorides Chemical class 0.000 description 19
- 230000032683 aging Effects 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- KMXTYZBQPJXGNK-UHFFFAOYSA-N hexadecan-1-amine;hydron;fluoride Chemical compound F.CCCCCCCCCCCCCCCCN KMXTYZBQPJXGNK-UHFFFAOYSA-N 0.000 description 3
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- BXGLGOSDYWTPSP-UHFFFAOYSA-N F.F.CCCCCCCCCCCCCCCCCCN Chemical compound F.F.CCCCCCCCCCCCCCCCCCN BXGLGOSDYWTPSP-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical class CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920000388 Polyphosphate Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 229940043256 calcium pyrophosphate Drugs 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 2
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229960001462 sodium cyclamate Drugs 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical class CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical class CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- IICFJQIXSKQPBC-UHFFFAOYSA-M 4,4-didodecylmorpholin-4-ium;fluoride Chemical compound [F-].CCCCCCCCCCCC[N+]1(CCCCCCCCCCCC)CCOCC1 IICFJQIXSKQPBC-UHFFFAOYSA-M 0.000 description 1
- VJFPOZFKRZTINH-UHFFFAOYSA-M 4-ethyl-4-tetradecylmorpholin-4-ium;fluoride Chemical compound [F-].CCCCCCCCCCCCCC[N+]1(CC)CCOCC1 VJFPOZFKRZTINH-UHFFFAOYSA-M 0.000 description 1
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 229910021593 Copper(I) fluoride Inorganic materials 0.000 description 1
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 240000001238 Gaultheria procumbens Species 0.000 description 1
- 235000007297 Gaultheria procumbens Nutrition 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 244000024873 Mentha crispa Species 0.000 description 1
- 235000014749 Mentha crispa Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 244000227633 Ocotea pretiosa Species 0.000 description 1
- 235000004263 Ocotea pretiosa Nutrition 0.000 description 1
- 235000011203 Origanum Nutrition 0.000 description 1
- 240000000783 Origanum majorana Species 0.000 description 1
- 238000013494 PH determination Methods 0.000 description 1
- XCOJIVIDDFTHGB-UEUZTHOGSA-N Perillartine Chemical compound CC(=C)[C@H]1CCC(\C=N\O)=CC1 XCOJIVIDDFTHGB-UEUZTHOGSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical class CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical class [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 125000006294 amino alkylene group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000011575 calcium Substances 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
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- IOLFKOXEKFYZCL-UHFFFAOYSA-N decyl(dimethyl)azanium fluoride Chemical compound [F-].C(CCCCCCCCC)[NH+](C)C IOLFKOXEKFYZCL-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- PQAZELNNXQQEAO-UHFFFAOYSA-M didodecyl(dimethyl)azanium;fluoride Chemical compound [F-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC PQAZELNNXQQEAO-UHFFFAOYSA-M 0.000 description 1
- DGTVXEHQMSJRPE-UHFFFAOYSA-M difluorophosphinate Chemical compound [O-]P(F)(F)=O DGTVXEHQMSJRPE-UHFFFAOYSA-M 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 229940104869 fluorosilicate Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 229910001385 heavy metal Chemical class 0.000 description 1
- SHVBTTRUEDMJTK-UHFFFAOYSA-N hexadec-1-en-1-amine Chemical class CCCCCCCCCCCCCCC=CN SHVBTTRUEDMJTK-UHFFFAOYSA-N 0.000 description 1
- 229940005740 hexametaphosphate Drugs 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical class CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 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
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 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 1
- 229940045919 sodium polymetaphosphate Drugs 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QHKIWQPIFXRUOW-UHFFFAOYSA-N tetracosan-1-amine Chemical class CCCCCCCCCCCCCCCCCCCCCCCCN QHKIWQPIFXRUOW-UHFFFAOYSA-N 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- YUOWTJMRMWQJDA-UHFFFAOYSA-J tin(iv) fluoride Chemical compound [F-].[F-].[F-].[F-].[Sn+4] YUOWTJMRMWQJDA-UHFFFAOYSA-J 0.000 description 1
- WSIJEESPTXCFJF-UHFFFAOYSA-H trimagnesium;diphosphate;trihydrate Chemical compound O.O.O.[Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WSIJEESPTXCFJF-UHFFFAOYSA-H 0.000 description 1
- KYPINKFMTJGZLG-UHFFFAOYSA-M trimethyl(octyl)azanium;fluoride Chemical compound [F-].CCCCCCCC[N+](C)(C)C KYPINKFMTJGZLG-UHFFFAOYSA-M 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/24—Phosphorous; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Description
GB2190288A 1
SPECIFICATION
Stabilized amine fluoride dental cream The present invention relates to a stabilized dental cream containing amine fluoride. In particular, 5 it relates to a dental cream containing amine fluoride which is stabilized against phase separation by the presence of low molecular weight polyethylene glycol.
Amine fluoride compounds have been proposed and used in dental creams and other types of oral compositions, such as mouthwashes, for their effect in promoting oral hygiene. For instance, they have the ability to increase resistance of dental enamel to acids, thereby improving the 10 ability of teeth to resist formation of cavities. They also can reduce formation of gingivitis and plaque in the oral cavity.
British Patents 865,272 and 1,021,058, each to Gaba A.G. describe oral compositions includ ing toothpastes and dental creams which contain amine fluoride compounds. In particular, in British Patent 1,021,058, amine fluoride dental cream compositions are specifically exemplified 15 wherein insoluble sodium metaphosphate is used as polishing agent, sorbitol is present as humectant and gelling agent, including methyl cellulose is also present. The patent also discusses glycerol (that is, glycerine) as an alternative humectant.
U.S. Patent 3,914,406 to Yankell also describes amine fluoride oral compositions including toothpastes and includes an example wherein insoluble sodium metaphosphate polishing agent, 20 sorbitol humectant and hydroxyethyl cellulose gelling agent are employed. The patent also discloses as humectants, -sorbitol, glycerine, polyhydric alcohols of like nature or mixtures thereof-. However, in the specific examples the only mixtures (sorbitol solution and glycerine) are used in mouthwashes, while the toothpastes contain either sorbitol solution or propylene glycol. 25 It has been observed that dental creams such as are generally characteristic of the prior art undergo phase separation when the polishing agent has a substantial content of insoluble alkali metal metaphosphate, the humectant is sorbitol or glycerine and the gelling agent is non-polar cellulosic material. Use of alternative polyhydric alcohol of like nature as the sole or main humectant, for instance in amounts of about 15% or more, has not been satisfactory. For 30 instance, when an amine fluoride dental cream containing 20% of polyethylene glycol of average molecular weight of about 600 is employed, an undesirable flavour note is provided.
It is an advantage of the present invention that separation in amine fluoride dental cream of a liquid phase from the solid or gelled portion of the dental cream is reduced or overcome.
In accordance with certain of its aspects the present invention relates to a dental cream 35 comprising a material which provides to the said dental cream about 0.01- 1% by weight of soluble fluoride, at least about 70% by weight of the said material being an amine fluoride, about 25-80% of an aqueous liquid phase comprising humectant in amount of at least about 20% by weight of the said dental cream, the said humectant being selected from the group consisting of sorbitol, glycerine and mixtures thereof, a solid phase comprising about 0.2-5% by 40 weight of a nonionic cellulosic gelling agent and about 20-75% by weight of a polishing material containing insoluble alkali metal metaphos-phate as at least the major components of the said polishing material, wherein the said dental cream is stabilised against phase separation by incorporation into the said aqueous humectant phase of polyethylene glycol having an average molecular weight of about 200-1000, wherein the weight ratio of the said humectant to the 45 said polyethylene glycol is from about 10:1 to about 12, the amount of polyethylene glycol being at least about 2% by weight.
The term amine fluoride as used herein, includes amine hydrofluorides as well as quaternary ammonium fluorides. These are employed in amounts which provide about 0. 01-1% by weight of soluble fluoride to the dental cream, preferably about 0.05-0.15%. 50 Typically, they are characterised as having the formula:
55.55 F W R 60 Wherein R represents an alkyl, alkenyl, alkylol, alkoxyalkyl, aryl, aryloxyalkyl, aralky], cycloalkyl, cycloalkenyl or heterocyclic group or an additional quaternary ammonium group which may be attached to the nitrogen atom by a bridging group or a group of the formula -R-CO.Y wherein Y represents an OH, alkoxy, cycloalkoxy, or aralkoxy group or 65 2 GB2190288A 2 R2 -N 5 R3 where R' represents an alkylene or arylene-alkylene and each of R 2 and R3 represent a hydrogen atom or an alkyl, alkenyi, alkylol, aryl, aralkyl, cycloalkyl or heterocyclic radical, or R2 and R3 form together with the nitrogen atom a heterocyclic nucleus, each one of the three free valences 10 being satisfied by an alkyl, alkenyl, alkylol, alkoxyalkyl, aryl, aryloxyalkyl, aralkyl, cycloalkyl, or heterocyclic group or at least two of the free valences being satisfied by a group forming together with the nitrogen atom, a saturated or unsaturated, unsubstituted or substituted heterocyclic nucleus. 15 The following compounds are specific examples of amine fluorides which may be employed in 15 accordance with the present invention. The invention is not intended to be limited to these compounds. Octyl-trimethyl-ammonium fluoride, dodecyi-ethyi-dimethyi-ammonium fluoride, tetraethyl ammonium fluoride, dilauryl-dimethyl-ammonium fluoride, 8,9 octadecenyi-benzyi-dimethyi-ammon- ium fluoride, furfuryi-iauryi-dimethyi-ammonium fluoride, phenoxyethyicetyl-dimethyi-ammon- 20 ium fluoride, N,N1-tetra-methyl-N,NI-dilauryi-ethylene-diammonium difluoride, N-cetyl-pyridi nium fluoride, N,N-dilauryl-morpholinium fluoride, N-myristyl-N-ethyl- morpholinium fluoride, N-(oetylamino-carbonylethyl)-N-benzyi-dimethyi-ammonium fluoride, N-(2 ethoxy-ethyi)-N-do decyl-dimethyl-ammonium fluoride, N-(o,-hydroxy-dodecyi)-trimethyi- ammonium fluoride, N-(2-carbomethoxy-ethyi)-N-benzyi-dimethyi-ammonium fluoride, N-(2-carbocyclo-hexoxy- 25 ethyi)-N myristyl-dimethyi-ammonium fluoride, N-(2-carbobenzyioxyethyi)-N- dodecyi-dimethyi- ammonium fluoride, N-(2-(NI, NI-dimethylamino-carbonyi)-ethyi-N-dodecyi- dimethyi-ammon- ium fluoride, and N-carboxy-methyi-N-eicosyi-dimethyi-ammonium fluoride.
The amine fluorides of the present invention are soluble in water, and most of them are also soluble in methanol and ethanol. There are mostly hygroscopic crystalline solids or syrups. 30 Those of the quaternary ammonium fluorides which have long-chain substituents dissolve in water with formation of foaming solutions.
Additional amine fluoride compounds which may be used in the present invention, and indeed are preferred, are amine hydrofluorides having the formula:
35 RXHF Wherein R represents an alkyl or alkenyl group having from about 10 to about 24 carbon atoms, advantageously from 14 to 21 carbon atoms; 40 R2 X represents - NH2 or -N- (CH2)y N 1 3 45 1 1 R R in which y is an integer of from 1 to 3, and R', R2 and R3 each represent a hydrogen atom; a 50 lower alkyl, lower alkenyl or lower alkanol group having up to 5 carbon atoms.
Exemplary of compositions of the present invention are those which comprise the hydrofluo ride salts of decylamine, dodecylamine, dodecenylamine, tetradecylamine, tetradecenylamine, pen tadecylamine, hexadecylamine, hexadecenylamine, octadecylamine, octadecenylamine, eicosylam ine, tetracosylamine, and N-(Bis-(hydroxyethyi)-aminopropyi)-N(hydroxyethyi) alkylamine 55 wherein the alkylamine is a mixture of alkylamine groups containing from about 12 to about 18 carbon atoms.
Advantageous compositions of the present invention are those which comprise 9-icta decbtwhich comprise 9-octadecnylarnine hydrofluoride, hexadecylamine hydrofluoride, N-(Bis-ffly droxyethyi)-aminopropyi)-N(hydroxyethyi)octadecylamine dihydrofluoride, or N,N,N-Tris-(2-hy- 60 droxyethyl 1)-N-octadecyi-l, 3-diamino-propane dihydrofluoride.
Further, a mixture of N-(Bis-(hydroxyethyi)-amino-propyi)-N(hydroxyethyi) octadecylamine dihydrofluoride and hexadecylamine hydrofluoride is also desirable.
In accordance with preferred aspects of the present invention, the entire soluble fluoride providing material is the amine fluoride. Also included are compositions in which up to 30% by 65 3 GB2190288A 3 weight of the soluble fluoride providing material may be an additional non-toxic, water-soluble fluoride-providing compound or mixture thereof. Among these additional compounds (including mixtures thereof) are inorganic salts which provide fluoride, such as suitable alkali metal, alkaline earth metal, and heavy metal salts, for example, sodium fluoride, potassium fluoride, ammonium fluoride, a copper fluoride, such as cuprous fluoride, zinc fluoride, a tin fluoride such as stannous 5 fluoride or stannous chlorofluoride, sodium fluorosilicate, ammonium fluorosilicate, sodium fluoro silicate, sodium fluorosilicate, ammonium fluorosilicate, sodium fluorozirconate, sodium monofluo rophosphate, aluminium mono and difluorophosphate, and fluorinated sodium calcium pyrophos phate. When present, alkali metal salts such as sodium fluoride and sodium monofluorophos- phate are preferred. 10 In dental cream formulations the liquids and solids are proportioned to form a creamy mass of desired consistency which is extrudable from a collapsible tube (for example, lacquered aluminum, wax-lined lead or laminated plastic) or a mechanically operated or pressure differential dispenser. The liquid phase comprises about 25-80% by weight of the dental cream and includes water together with at least one of sorbitol and glycerine as humectant, the amount of 15 sorbitol and/or glycerine being at least about 20% by weight of the dental cream, preferably about 20-40%. Sorbitol is the preferred humectant and is typically employed as a 70% aqueous solution. Water is present, typically in amount of at least about 5% by weight, preferably about 15-40%.
The gelling agent for use in the dental cream formulations of the present invention is a 20 nonionic cellulosic gelling agent, such as methyl cellulose, hydroxymethyl cellulose, ethyl cellu lose, hydroxyethyl cellulose, propyl cellulose, hydroxypropyl cellulose and the like. Hydroxyethyl cellulose is preferred. The gelling agent is present in an amount of about 0.2-5% by weight of the dental cream, preferably about 0.13-2.0%.
Grades of hydroxyethyl cellulose which may be used include those given in Table 1 below: 25 TABLE 1
SUPPLIER HEC GRADE VISCOSITY (CPS) Hercules Natrosol 250M and MR 4500 6500 30 Natrosol 250 HR 1500 - 2500 and 250 H Natrosol 250 HHR 3400 - 5000 35 and 250 HH B.P. Chemicals Cellobond 5000 A 4200 - 5600 11 Cellobond 7000 A 6000 - 7000 40 Hoechst Tylose H 4000 P 3000 - 5000 Tylose H 10000 P 7000 - 12000 Notes on Table 1 45 1% solution (Brookfield; 25oC)
Hoeppler Viscometer (2%; 20OC) Natrosol 250 M is preferred. 50 The polishing material employed in the dental cream formulations is present in amounts of about 20-75% by weight, preferably about 35-65%. Most preferably it is all or substantially all insoluble alkali metal metaphosphate. It is within the scope of the present invention that insol55 uble alkali metal metaphosphate may be present as the major polishing agent (at least 50.0%) in admixutre with a minor amount of secondary polishing agent, such as calcined alumina, decal cium phosphate (anhydrous or dihydrate), calcium pyrophosphate, tricaicium phosphate, calcium carbonate, trimagnesium phosphate trihydrate and magnesium carbonate. When secondary pol ishing agent is present, it is preferred that it be in amount of up to about one-third the amount 60 of insoluble alkali metal metaphosphate, with the weight ratio of insoluble alkali metal metaphos phate to secondary polishing agent being about 3:1 to about 99A, preferably about 8:1 to about 12: 1.
Insoluble sodium metaphosphate is the preferred salt of the waterinsoluble alkali metal polym etaphosphates. It is known, for example, as Maddrell or Kurrol salt. Water-soluble polymetaphos- 65 4 GB2190288A 4 phates such as di-, tri-, tetra-, or hexa-metaphosphate are not intended to be covered by the invention. These latter may, however, be present as impurities in the water-insoluble polymetaphosphates which can be used in accordance with the invention. The commercially available water-insoluble sodium polymetaphosphate may for example, contain up to 4% of a watersoluble metaphosphate. 5 Low molecular weight polyethylene glycol of average molecular weight of about 200-1000, preferably about 400-1000, disperses readily in the liquid vehicle and is effective to prevent the dental cream from undergoing phase separation or syneresis. In order to effect dispersion readily, grades of polyethylene glycol which are normally solid at room temperature are heated to liquify them. Low molecular weight polyethylene glycol is employed in amount such that the 10 weight ratio of humectant (glycerine and/or sorbitol) to polyethylene glycol is from about 10:1 to about 1:2, preferably from about 2:1 to about 1A. the polyethylene glycol is present in amount of at least about 2%, by weight, typically about 2-10% and preferably about 4-10%. Organic surface-active agents may be used in the dental cream of the present invention to achieve increased prophylactic action, assist in achieving thorough and complete dispersion of the com- 15 positions of the present invention throughout the oral cavity, and render the dental creams more cosmetically acceptable. The organic surface-active material is typically non-ionic, ampholytic or cationic in nature, and it is preferred to employ as the surface-active agent a detersive material which imparts to the composition detersive properties.
Suitable surface-active materials include nonionic agents such as condensates of sorbitan 20 monostearate with approximately 20 moles of ethylene oxide, condensates of ethylene oxide with propylene glycol (---Pluronic- materials) and amphoteric agents such as long chain (alkyl) amino-alkylene alkylated amine derivatives, which are available under the trademark---Miranol such as Miranol C2M. Cationic surface-active germicides and antibacterial compounds such as di-isobutyl phenoxy ethoxy ethyl dimethyl benzyi ammonium chloride, benzyi dimethyl steary] 25 ammonium chloride, benzyl dimethyl stearyl ammonium chloride, tertiary amines having one fatty alkyl group (of from 12-18 carbon atoms) and two (poly) oxyethylene groups attached to the nitrogen (typically containing a total of from about 2 to 50 ethanoxy groups per molecule) and salts thereof with acids, and compounds of the structure 30 (CH2 CH 2 0) Z H (CH2CH20) X H 11 i-CH2CH2CH2-N-(CH2CH20) Y H 35 where R represents a fatty alkyl group containing from about 12 to 18 carbon atoms, and x, y and z total 3 or higher, as well as salts thereof with mineral or organic acids, may also be used. 40 It is preferred to use about 0.05-5% by weight of surface-active material.
Any suitable flavouring or sweetening materials may be employed in formulating a flavour for the composition of the present invention. Examples of suitable flavouring constituents include the flavouring oils, e.g. oils of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyp tus, marjoram, cinnamon, lemon and orange, as well as methyl salicylate. Suitable sweetening 45 agents include sucrose, lactose, maltose, xylitol, sodium 6-methyl-3, 4- dihydro-1, 2, 3-oxathi azine-4-one, sodium cyclamate, perillartine, sodium saccharin and saccharin acid. Suitably, flavour and sweetening agents may together comprise from about 0.01 to 5% or more of the compositions of the present invention.
Various other materials may be incorporated in the dental cream. Examples thereof are colour- 50 ing or whitening agents or dyestuffs, preservatives, anti-corrosive agents, silicones, chlorophylic compounds, additional ammoniated materials such as urea, diammonium phosphate and mixtures thereof and other constituents. Whitening agents, such as titanium dioxide, typically in amounts of about 0.05-2%, may be beneficial to the appearance of the dental composition, since upon aging, some discolouration may occur. 55 The adjuvants are incorporated in the compositions of the present invention in amounts which do not substantially adversely affect the properties and characteristics desired and are selected and used in proper amounts depending upon the particular type of compositions involved.
Antibacterial agents may also be employed in the oral compositions of the present invention in an amount of about 0.01-5% by weight. 60 When an insoluble alkaline earth metal salt is present as the secondary polishing agent, there is typically employed various calcium and magnesium ion suppression agents for adjustment of physical properties of the compositions. Suitable agents are the water- soluble inorganic poly phosphate salts, such as tetrasodium pyrophosphate or disodium diacid pyrophosphate, with the partially neutralized or acid polyphosphate preferred. Other suitable agents are the alkali metal, 65 GB2190288A 5 preferably sodium, salts of citric acid. In general, such compounds will be a minor amount or proportion of the formulation. The precise amount will vary depending upon the specific formula tion, such as the physical characteristics of the dental cream, but will usually be from a-bout 0 1 % to about 3% by weight.
The dental creams should have a pH practicable for use. A pH range of about 3.5 to 9 is 5 particularly desirable. The reference to the pH is meant to be the pH determination directly on the dental cream. If desired, materials such as citric acid may be added to adjust the pH to say preferably about 4-8.
The invention may be put into practice in various ways and a number of specific embodiments will be described by way of example to illustrate the invention with reference to the accompany- 10 ing examples. All amounts and proportions are by weight except as otherwise indicated.
EXAMPLES 1A and 18 The following dental creams having the ingredients and proportions set out in Table 2 are prepared: 15 TABLE 2
Examples 1A 1B Ingredients 20 Glycerine 23.0 13.0 Polyethylene Glycol 600 - 10.0 Hydroxyethyl Cellulose (Natrosol 1.5 1.5 25 25OM) Sodium Saccharin 0.4 0.4 Water (Deionised) 27.1 27.1 30 Titanium Dioxide 0.5 0.5 Amine Fluoridel 33% 4.0 4.0 Insoluble Sodium Metaphosphate 42.0 42.0 35 Polyoxyethylene Sorbitan - 0.5 0.5 Ethylene Oxide (20:1) Monostearate 40 Flavour 1.1 1.1 Note on Table 2 45 1 The Amine Fluoride is N,N,N-tris (2-hydroxyethyi)-N-octadecyi-l, 3- diaminopropane dihy drofluoride.
In preparing the above dental cream polyethylene glycol 600 is dispersed with glycerine prior to addition of hydroxyethyl cellulose to form a product of creamy consistency.
After aging for 12 weeks at 43'C the dental cream of Example 113 remains substantially 50 rheologically stable while substantial syneresis of the dental cream of Example 1A is observed within 4 weeks.
EXAMPLES 2A and 28 Dental creams are prepared corresponding to the dental creams of Examples 1A and 113 55 respectively, except that sorbitol (70%) replaces glycerine.
After aging for 12 weeks at 43'C only very slight phase separation is observed with the dental cream of Example 213 while substantial syneresis of the dental cream of Example 2A is observed within 2 weeks.
60 EXAMPLES 3A to 3E The amounts of glycerine and polyethylene glycol 600 in the dental cream of Example 113 are varied as given in Table 3 below:
6 GB2190288A 6 TABLE 3
Glycerine Polyethylene Glycol 600 Example Parts Parts 3A 20.0 2.0 5 313 19.0 3.0 3C 18.0 4.0 3D 16.0 6.0 3E 14.0 8.0 10 After aging for 3 weeks at 49'C, only very slight phase separation is observed with the dental cream of Example 3A, only very slight phase separation with the dental creams of Examples 313 and 3C after 9 weeks at 49'C and substantially no phase separation is observed with the dental creams of Examples 3D and 3E even after aging for 9 weeks at 49'C.
15 EXAMPLES 4A to 4D Polyethylene glycol of average molecular weights indicated below is used to replace polyethylene glycol 600 in the dental cream of Example 113 with the amounts of glycerine and polyethylene glycol also varied as indicated in Table 4 below:
20 TABLE 4
Polyethylene Glycol Glycerine Average Example Parts Mol. wt. Parts 4A 18.000 400 4.000 25 413 16.000 400 6.000 4C 18.000 1000 4.000 41) 16.000 1000 6.000 After aging for 9 weeks at 49'C there is substantially no phase separation with the dental 30 creams of Examples 4A and 4C, only very very slight phase separation with the dental cream of example 413 and only very slight phase separation with the dental cream of Example 4C. In the dental creams of Examples 4A and 4D glycerine is heated to WC prior to dispersion of polyethylene glycol 1000 therein.
35 EXAMPLES 5A to 5C The amounts of sorbitol (70%) and polyethylene glycol 600 in the dental cream of Example 213 is varied as given in Table 5 below:
TABLE 5 40
Sorbitol (70 %) Polyethylene Glycol 600 Examples Parts Parts 5A 18.000 4.000 513 17.000 5.000 5C 16.000 6.000 45 After aging for 9 weeks at 4WC there is substantially no phase separation with the dental creams of Examples 5A and 5C and only an indication of very slight phase separation with the dental cream of Example 5B.
50 EXAMPLE 6
A dental cream which does not separate into phases upon aging is prepared by varying the dental cream of Example 213 to reduce the amount of insoluble sodium metaphosphate to 37.8 parts and including 4.2 parts of calcined alumina.
55 EXAMPLES 7A and 7B The following dental creams having the ingredients and proportins given in Table 6 do not separate into phases upon aging.
7 GB2190288A 7 TABLE 6
Examples 7A 7B Ingredients Parts 5 Glycerine 16.000 16.000 Polyethylene Glycol 600 6.000 6.000 Hydroxyethyl cellulose (Natrosol 1.500 1.500 10 250M) Sodium Saccharin 0.400 0.400 Water (Deionised) 29.133 29.053 15 Titanium Dioxide 0.500 0.500 Amine Fluoride' (33%) 2.800 2.800 Sodium Monofluorophosphate - 0.114 20 Sodium Fluoride 0.067 0.033 Insoluble Sodium Metaphosphate 42.000 42.000 Polyoxyethylene Sorbitan- 0.500 0.500 25 Ethylene Oxide (20:1) Monostearate Flavour 1.1 1.1 30 Note on Table 6 35 1 The Amine Fluoride is N,N,N-tris (2-hydroxyethyi)-N-octadecyi-l, 3diaminopropane dihy drofluoride.
In the foregoing examples, the 4.0 parts of the 33% solution of the Amine Fluoride may be replaced by 4.344 parts of a 1:4 mixture of N-(Bis-(hydroxyethyi)- aminopropyi)-N-(hydroxye- 40 thyl) octadecylamine dihydrofluoride and hexadecylamine hydrofluoride, with similar results.
In the foregoing examples, sodium cyclamate may replace sodium saccharine.
It is apparent that the above examples illustrate the invention and various modifications may be made thereto.
45
Claims (16)
1. A dental cream comprising a material which provides to the said dental cream about 0.01-1% by weight of soluble fluoride, at least about 70% by weight of the said material being an amine fluoride, about 25-80% of an aqueous liquid phase comprising humectant in amount of at least about 20% by weight of the said dental cream, the said humectant being selected from 50 the group consisting of sorbitol, glycerine and mixture thereof, a solid phase comprising about 0.2-5% by weight of a nonionic cellulosic gelling agent and about 20-75% by weight of a polishing material containing insoluble alkali metal metaphosphate as at least the major compo nents of the said polishing material, wherein the said dental cream is stabilised against phase separation by incorporation into the said aqueous humectant phase of polyethylene glycol having 55 an average molecular weight of about 200-1000, wherein the weight ratio of the said humec tant to the said polyethylene glycol is from about 10:1 to about 1:2, the amount of polyethylene glycol being at least about 2% by weight.
2. A dental cream as claimed in Claim 1 in which the said amine fluoride is present in an amount which provides about 0.05-0.15% by weight of soluble fluoride. 60
3. A dental cream as claimed in Claim 1 or Claim 2 in which the said amine fluoride is N,N,N-tris (2-hydroxyethyi)-N-octadecyi-l, 3-diaminopropane dihydrofluoride.
4. A dental cream as claimed in Claim 1, 2 or 3 in which the said nonionic cellulosic gelling agent is present in an amount of about 0.8-2% by weight.
5. A dental cream as claimed in any one of Claims 1 to 4 in which the said nonionic 65 8 GB2190288A 8 cellulosic gelling agent is hydroxyethyl cellulose.
6. A dental cream as claimed in anyone of claims 1 to 5 in which the said polishing agent is present in an amount of about 35-65% by weight.
7. A dental cream as claimed in any one of Claims 1 to 6 in which the said insoluble alkali metal metaphosphate is insoluble sodium metaphosphate. 5
8. A dental cream as claimed in Claim 7 in which the said insoluble sodium metaphosphate is the sole polishing material present.
9. A dental cream as claimed in any one of Claims 1 to 8 in which the said polyethylene glycol is present in an amount of about 2-10% by weight.
10. A dental cream as claimed in Claim 9 in which the said polyethylene glycol is present in 10 an amount of about 4-10%.
11. A dental cream as claimed in any one of Claims 1 to 10 in which the said polyethylene glycol has an average molecular weight of about 400-1000.
12. A dental cream as claimed in Claim 11 in which the said polyethylene glycol has an average molecular weight of about 600. 15
13. A dental cream as claimed in any one of Claims 1 to 12 in which the said amine fluoride is the sole fluoride providing material present.
14. A dental cream as claimed in any one of Claims 1 to 13 in which up to about 30% of the fluoride providing material is inorganic fluoride providing salt.
15. A dental cream as claimed in Claim 14 in which the said inorganic fluoride providing salt 20 is selected from the group consisting of sodium fluoride, sodium monofluorophosphate and mixture thereof.
16. A dental cream as claimed in Claim 1 substantially as specifically described herein with reference to any one of Examples 1 B, 213, 3A to 3E, 4A to 4D, 5A to 5C, 6 or 7A or 7B.
Printed for Her Majesty's Stationery Office by Burgess & Son (Abingdon) Ltd, Dd 8991685, 1987.
Published at The Patent Office, 25 Southampton Buildings, London, WC2A 1 AY, from which copies may be obtained.
1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86284286A | 1986-05-13 | 1986-05-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8711302D0 GB8711302D0 (en) | 1987-06-17 |
| GB2190288A true GB2190288A (en) | 1987-11-18 |
| GB2190288B GB2190288B (en) | 1990-03-28 |
Family
ID=25339512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8711302A Expired - Lifetime GB2190288B (en) | 1986-05-13 | 1987-05-13 | Stabilized amine fluoride dental cream |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT390190B (en) |
| CH (1) | CH674803A5 (en) |
| DE (1) | DE3715366A1 (en) |
| DK (1) | DK240887A (en) |
| FR (1) | FR2598612B1 (en) |
| GB (1) | GB2190288B (en) |
| NL (1) | NL8701141A (en) |
| SE (1) | SE8701877L (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2457829C2 (en) * | 2010-11-08 | 2012-08-10 | Общество С Ограниченной Ответственностью "Сплат-Косметика" (Ооо "Сплат-Косметика") | Mineral and vitamin complex for strengthening tooth enamel, composition for oral cavity hygiene and toothpaste |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102013210931A1 (en) | 2013-06-12 | 2014-12-18 | Henkel Ag & Co. Kgaa | Liquid toothpaste with amine fluoride (s) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL108645C (en) * | 1958-05-29 | |||
| FR2849M (en) * | 1961-11-01 | 1964-10-19 | Gaba Ag | Composition for dental care. |
| ZA737495B (en) * | 1972-10-30 | 1975-05-28 | Colgate Palmolive Co | Toothpastes |
| US3914406A (en) * | 1973-12-28 | 1975-10-21 | Menley & James Lab Ltd | Compositions and method for prevention and treatment of gingivitis |
| US4490353A (en) * | 1983-07-13 | 1984-12-25 | Colgate-Palmolive Company | Antiplaque dentifrice with improved fluoride stability |
| US4584189A (en) * | 1984-09-28 | 1986-04-22 | Hercules Incorporated | Bactericidal toothpastes |
-
1987
- 1987-05-07 SE SE8701877A patent/SE8701877L/en not_active Application Discontinuation
- 1987-05-08 CH CH175687A patent/CH674803A5/de not_active IP Right Cessation
- 1987-05-08 DE DE19873715366 patent/DE3715366A1/en not_active Withdrawn
- 1987-05-12 DK DK240887A patent/DK240887A/en not_active Application Discontinuation
- 1987-05-12 AT AT0119287A patent/AT390190B/en not_active IP Right Cessation
- 1987-05-13 NL NL8701141A patent/NL8701141A/en not_active Application Discontinuation
- 1987-05-13 FR FR8706733A patent/FR2598612B1/en not_active Expired - Lifetime
- 1987-05-13 GB GB8711302A patent/GB2190288B/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2457829C2 (en) * | 2010-11-08 | 2012-08-10 | Общество С Ограниченной Ответственностью "Сплат-Косметика" (Ооо "Сплат-Косметика") | Mineral and vitamin complex for strengthening tooth enamel, composition for oral cavity hygiene and toothpaste |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3715366A1 (en) | 1987-11-26 |
| FR2598612A1 (en) | 1987-11-20 |
| SE8701877D0 (en) | 1987-05-07 |
| GB8711302D0 (en) | 1987-06-17 |
| NL8701141A (en) | 1987-12-01 |
| CH674803A5 (en) | 1990-07-31 |
| GB2190288B (en) | 1990-03-28 |
| SE8701877L (en) | 1987-11-14 |
| DK240887D0 (en) | 1987-05-12 |
| FR2598612B1 (en) | 1991-05-03 |
| ATA119287A (en) | 1989-09-15 |
| AT390190B (en) | 1990-03-26 |
| DK240887A (en) | 1987-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930513 |