WO2011160996A1 - Non-aqueous oral care compositions - Google Patents
Non-aqueous oral care compositions Download PDFInfo
- Publication number
- WO2011160996A1 WO2011160996A1 PCT/EP2011/060003 EP2011060003W WO2011160996A1 WO 2011160996 A1 WO2011160996 A1 WO 2011160996A1 EP 2011060003 W EP2011060003 W EP 2011060003W WO 2011160996 A1 WO2011160996 A1 WO 2011160996A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- polyethylene glycol
- oral care
- melting point
- mixture
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 115
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 41
- 239000007788 liquid Substances 0.000 claims abstract description 25
- 239000000551 dentifrice Substances 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 21
- 239000003906 humectant Substances 0.000 claims abstract description 16
- 238000002844 melting Methods 0.000 claims abstract description 16
- 230000008018 melting Effects 0.000 claims abstract description 16
- 239000002562 thickening agent Substances 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 28
- 229920002125 Sokalan® Polymers 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- -1 allyl ethers Chemical class 0.000 claims description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000378 calcium silicate Substances 0.000 claims description 6
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 6
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical group [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 6
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 6
- 239000001488 sodium phosphate Substances 0.000 claims description 6
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 6
- 235000019801 trisodium phosphate Nutrition 0.000 claims description 6
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims description 6
- 239000012459 cleaning agent Substances 0.000 claims description 5
- 229920001519 homopolymer Polymers 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 4
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 125000006353 oxyethylene group Chemical group 0.000 claims description 3
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- KUQWZSZYIQGTHT-UHFFFAOYSA-N hexa-1,5-diene-3,4-diol Chemical compound C=CC(O)C(O)C=C KUQWZSZYIQGTHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 238000009472 formulation Methods 0.000 abstract description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 8
- 229960005069 calcium Drugs 0.000 description 7
- 235000001465 calcium Nutrition 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 235000012241 calcium silicate Nutrition 0.000 description 5
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000004141 Sodium laurylsulphate Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 229940091249 fluoride supplement Drugs 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000003082 abrasive agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003755 preservative agent Substances 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
- 239000000377 silicon dioxide Substances 0.000 description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- MCNJOIMMYWLFBA-UHFFFAOYSA-N 2-dodecoxy-2-oxoethanesulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCCOC(=O)CS(O)(=O)=O MCNJOIMMYWLFBA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000001736 Calcium glycerylphosphate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-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
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000002272 anti-calculus Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- UILNZNXXNSBJFL-UHFFFAOYSA-N azanium;cobalt;fluoride Chemical compound [NH4+].[F-].[Co] UILNZNXXNSBJFL-UHFFFAOYSA-N 0.000 description 1
- BHVHWURIWAJJON-UHFFFAOYSA-N azanium;tin;fluoride Chemical compound [NH4+].[F-].[Sn] BHVHWURIWAJJON-UHFFFAOYSA-N 0.000 description 1
- XVRKEHYQBKGNBA-UHFFFAOYSA-N azanium;zinc;fluoride Chemical compound [NH4+].[F-].[Zn] XVRKEHYQBKGNBA-UHFFFAOYSA-N 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 239000000872 buffer Substances 0.000 description 1
- 239000000648 calcium alginate Substances 0.000 description 1
- 235000010410 calcium alginate Nutrition 0.000 description 1
- 229960002681 calcium alginate Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
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- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical class [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000004227 calcium gluconate Substances 0.000 description 1
- 235000013927 calcium gluconate Nutrition 0.000 description 1
- 229960004494 calcium gluconate Drugs 0.000 description 1
- UHHRFSOMMCWGSO-UHFFFAOYSA-L calcium glycerophosphate Chemical compound [Ca+2].OCC(CO)OP([O-])([O-])=O UHHRFSOMMCWGSO-UHFFFAOYSA-L 0.000 description 1
- 229940095618 calcium glycerophosphate Drugs 0.000 description 1
- 235000019299 calcium glycerylphosphate Nutrition 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
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- 229940095643 calcium hydroxide Drugs 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 1
- 239000001527 calcium lactate Substances 0.000 description 1
- 235000011086 calcium lactate Nutrition 0.000 description 1
- 229960002401 calcium lactate Drugs 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229940087373 calcium oxide Drugs 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 229960001714 calcium phosphate Drugs 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000011635 calcium salts of citric acid Substances 0.000 description 1
- 235000019842 calcium salts of citric acid Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 1
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 1
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- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
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- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical class [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 239000011775 sodium fluoride Substances 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
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- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 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
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- 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
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/30—Characterized by the absence of a particular group of ingredients
- A61K2800/31—Anhydrous
Definitions
- the present invention is concerned with non-aqueous oral care compositions.
- compositions such as dentifrices typically contain dentally acceptable abrasive, humectant, water, and water-soluble polymer which serves as a thickener and binder for the ingredients.
- dentally acceptable abrasive, humectant, water, and water-soluble polymer which serves as a thickener and binder for the ingredients.
- other ingredients such as flavours, sweeteners, preservatives and fluoride are also utilized at low levels.
- flavours, sweeteners, preservatives and fluoride are also utilized at low levels.
- materials which are physically or chemically
- Non-aqueous formulations have been suggested as a way of improving the stability of these materials.
- WO96/03108 describes a non-aqueous dentifrice composition comprising a carboxyvinyl polymer, a humectant, a polyethylene glycol and a dentally acceptable abrasive.
- the carboxyvinyl polymer is stated to thicken the humectant materials and provide the necessary rheology in order to suspend any required abrasive material.
- a polyethylene glycol selected from PEG 300 and PEG 400 is stated to reduce stickiness from the formulation and give a smooth textured product.
- WO96/03108 is that they do not behave Theologically like a typical aqueous dentifrice. This problem is observed both during manufacture and during use by the consumer. It has led to manufacturing difficulties and reduced acceptance amongst consumers. Viscosity profile and flow characteristics are key factors governing ease of processing, product performance and consumer perception of a dentifrice.
- the present invention provides a non-aqueous oral care composition with a liquid continuous phase comprising a thickening agent, a humectant, and one or more liquid polyethylene glycols having a melting point below 25°C, in which the liquid continuous phase is structured with crystals of one or more solid polyethylene glycols having a melting point of 25°C or above.
- composition of the invention corresponds well with the characteristic rheological behaviour of typical aqueous dentifrice formulations. This correspondence is observed across a wide range of conditions of temperature and shear. Compared to previous non-aqueous dentifrice formulations, the composition of the invention has improved microstructure, ease of processing and excellent sensory properties.
- composition of the invention is its thermal storage stability across an extended range of temperature. Contrary to what has been observed in previous anhydrous dentifrice formulations, the composition of the invention remains fully stable and functional at temperatures as low as 5°C and as high as 50°C. Detailed Description of the Invention
- the composition of the invention is non-aqueous.
- non-aqueous it is generally meant that water is not deliberately added to the composition in any significant quantity.
- non-aqueous does not mean that small amounts of water cannot be present, for example as a consequence of its association with hygroscopic raw materials.
- non-aqueous generally means that water is present in an amount no greater than about 5%, more preferably no greater than about 3% by weight based on the total weight of the composition.
- the liquid continuous phase of the composition of the invention comprises a thickening agent.
- the thickening agent helps to impart a desirable viscosity profile and desirable flow characteristics to the composition.
- Suitable thickening agents for use in the invention are those which are operable in non-aqueous systems. Examples of such materials include organic
- macromolecules which do not necessarily require hydration with water in order to build viscosity, but can also build viscosity by alternative mechanisms such as by hydrogen bonding in the presence of hydroxyl donors such as polyols.
- Carboxyvinyl polymers have been found to be useful in this context.
- Preferred carboxyvinyl polymers for use in the invention have a molecular weight of at least about 750,000, more preferably at least about 1 ,250,000, most preferably at least about 3,000,000 g/mol.
- a suitable chemical class of such carboxyvinyl polymers for use in the invention includes crosslinked polymers having a polymer backbone derived from acrylic acid, substituted acrylic acid, or salts or esters thereof, in which the crosslinking agent contains two or more carbon-carbon double bonds and is derived from a polyhydric alcohol. Specific examples of such materials are homopolymers of acrylic acid cross-linked with allyl ethers of sucrose or
- carboxyvinyl polymer for use in the compositions of the present invention is a homopolymer of acrylic acid crosslinked with allyl ethers of pentaerythritol, which is slightly pre-neutralised (1 to 3%) by potassium salt. This pre-neutralisation is done in order to precipitate polyacrylic acid in the presence of the polymerisation solvent.
- a material is commercially available, for example, as CARBOPOL® 974P NF Polymer, ex Lubrizol Advanced Materials, Inc. Mixtures of any of the above described materials may also be used.
- the level of thickening agent will depend on the particular type chosen, but generally ranges from 0.05 to 10% by total weight thickener based on the total weight of the composition.
- the thickening agent is a carboxyvinyl polymer (as described above)
- the amount of carboxyvinyl polymer in compositions of the invention suitably ranges from 0.05 to 5%, preferably from 0.1 to 2%, more preferably from 0.2 to 0.5% by total weight carboxyvinyl polymer based on the total weight of the composition.
- the liquid continuous phase of the composition of the invention comprises a humectant.
- the humectant helps to keep the composition from hardening or crystallizing upon exposure to air. It also helps to give the composition a moist feel to the mouth, and may in some cases impart a desirable sweetness.
- Preferred humectants for use in the invention include organic polyols having 3 or more hydroxyl groups in the molecule (hereinafter termed "organic polyols").
- Examples of such materials include glycerol, sorbitol, xylitol, mannitol, lactitol, maltitol, erythritol, and hydrogenated partially hydrolyzed polysaccharides.
- the most preferred organic polyol is glycerol. Mixtures of any of the above described materials may also be used.
- the level of humectant will depend on the particular type chosen, but generally ranges from about 20 to 90% by weight based on the total weight of the composition.
- the humectant is one or more organic polyols (as described above)
- the amount of organic polyol suitably ranges from 35 to 75%, more preferably from 45 to 70% by total weight organic polyol based on the total weight of the composition.
- the composition of the invention is organic polyol-based.
- organic polyol- based means that the composition is not oil-based or water-based, but instead, organic polyols (as defined above) are a principal component in the composition.
- composition of the invention is glycerol-based (i.e glycerol makes up a higher portion of the composition's weight than any other compound) and contains from 45 to 70% by weight glycerol based on the total weight of the composition.
- the liquid continuous phase of the composition of the invention is structured with crystals of one or more solid polyethylene glycols having a melting point of 25°C or above.
- the melting point ranges from 35 to 65°C, more preferably from 55 to 60° C.
- the crystals of the solid polyethylene glycol(s) help to provide an optimised microstructure for the composition.
- Polyethylene glycols have the general formula H(OCH 2 CH 2 )n OH, where n is the number of repeating oxyethylene units.
- Commercially available polyethylene glycols are usually not uniform chemical compounds, but instead consist of a distribution of similar polymer members of the homologous polyethylene glycol series, defined by average values of n and molecular weight.
- the melting point generally increases with increasing average values of n and molecular weight.
- Suitable solid polyethylene glycols have an average value of n in the above general formula ranging from about 20 to 220, preferably from about 40 to 150, more preferably from about 32 to 90, most preferably from about 60 to 75.
- the average molecular weight suitably ranges from about 950 to 1 1 ,250, preferably from about 1800 to 6600, more preferably from about 1400 to 4400, most preferably from about 2700 to 3700 g/mol.
- Suitable commercially available materials include for example Polyglykol® 3000 (ex Clariant). Mixtures of any of the above described materials may also be used.
- the amount of solid polyethylene glycol (as defined above) in compositions of the invention suitably ranges from 0.1 to 5%, preferably from 0.5 to 3%, more preferably from 1 to 2.5% by total weight solid polyethylene glycol (as defined above) based on the total weight of the composition.
- the liquid continuous phase of the composition of the invention one or more liquid polyethylene glycols having a melting point below 25°C.
- the melting point ranges from -50 to 22°C, more preferably from -15 to 8° C, most preferably from 4 to 8°C.
- the liquid polyethylene glycol(s) helps to make processing of the composition easier, especially at high shear, by reducing the overall viscosity of the liquid continuous phase.
- Preferred liquid polyethylene glycols have an average value of n in the general formula ⁇ ( ⁇ 2 ⁇ 2 ) ⁇ ⁇ (as described above) ranging from about 4 to 12, more preferably about 6 to 8, most preferably about 8.
- the average molecular weight suitably ranges from about 190 to 630, more preferably from about 285 to 420, most preferably from about 380 to 420 g/mol.
- Suitable commercially available materials include for example PEG 400 (ex BDH Chemicals). Mixtures of any of the above described materials may also be used.
- liquid polyethylene glycol (as defined above) in compositions of the invention suitably ranges from 1 to 20%, preferably from 5 to 15%, more preferably from 8 to 12% by total weight liquid polyethylene glycol (as defined above) based on the total weight of the composition.
- the composition of the invention is typically in the form of a dentifrice.
- dentifrice denotes a formulation which are used to clean the surfaces of the oral cavity.
- the dentifrice is an oral composition that is not intentionally swallowed for purposes of systemic administration of therapeutic agents, but is retained in the oral cavity for a sufficient time to contact substantially all of the dental surfaces and/or mucosal tissues for purposes of oral activity.
- the dentifrice is suitable for application with a toothbrush and is rinsed off after use.
- the dentifrice is in the form of an extrudable semi-solid such as a cream, paste or gel (or mixture thereof).
- a dentifrice composition according to the invention will generally contain further ingredients to enhance performance and/or consumer acceptability such as abrasive cleaning agent and surfactant.
- a dentifrice will usually comprise an abrasive cleaning agent in an amount of from 3 to 75% by weight based on the total weight of the dentifrice.
- Suitable abrasive cleaning agents include particulate abrasive materials such as abrasive silicas, aluminas, calcium carbonates, zirconium silicate,
- polymethylmethacrylate polymethylmethacrylate, dicalcium phosphates, calcium pyrophosphates, hydroxyapatites, trimetaphosphates, insoluble hexametaphosphates and agglomerates and/or mixtures thereof.
- a dentifrice will usually contain a surfactant in an amount of from 0.2 to 5% by weight based on the total weight of the dentifrice.
- Suitable surfactants include anionic surfactants, such as the sodium, magnesium, ammonium or ethanolamine salts of Cs to Cis alkyl sulphates (for example sodium lauryl sulphate), Cs to Cis alkyl sulphosuccinates (for example dioctyl sodium
- Cs to Cis alkyl sulphoacetates such as sodium lauryl sulphoacetate
- Cs to Cis alkyl sarcosinates such as sodium lauryl sarcosinate
- Cs to Cis alkyl phosphates which can optionally comprise up to 10 ethylene oxide and/or propylene oxide units) and sulphated monoglycerides.
- Suitable surfactants include nonionic surfactants, such as optionally polyethoxylated fatty acid sorbitan esters, ethoxylated fatty acids, esters of polyethylene glycol, ethoxylates of fatty acid monoglycerides and diglycerides, and ethylene oxide/propylene oxide block polymers.
- suitable surfactants include amphoteric surfactants, such as betaines or sulphobetaines. Mixtures of any of the above described materials may also be used.
- the composition of the invention is particularly suitable as a vehicle for oral care actives which may be physically or chemically incompatible with water, or which may function less efficiently in an aqueous environment.
- Specific examples of oral care actives which may be included in the compositions of the invention include: fluoride sources such as sodium fluoride, stannous fluoride, sodium
- compositions of the invention include agents for the remineralisation of teeth.
- remineralisation in the context of the present invention means the in situ generation of hydroxyapatite on teeth.
- a specific example of a suitable agent for the remineralisation of teeth is a mixture of a calcium source and a phosphate source which, when delivered to the teeth results in the in situ generation of hydroxyapatite on teeth.
- remineralising calcium sources include, for example, calcium phosphate, calcium gluconate, calcium oxide, calcium lactate, calcium glycerophosphate, calcium carbonate, calcium hydroxide, calcium sulphate, calcium carboxymethyl cellulose, calcium alginate, calcium salts of citric acid, calcium silicate and mixtures thereof.
- the remineralising calcium source is calcium silicate.
- the amount of remineralising calcium source(s) (e.g. calcium silicate) in the composition of the invention typically ranges from 1 to 30%, preferably from 5 to 20% by total weight remineralising calcium source based on the total weight of the oral care composition.
- remineralising phosphate sources include, for example, sodium dihydrogen phosphate, disodium hydrogen phosphate, sodium pyrophosphate, tetrasodium pyrophosphate, sodium tripolyphosphate, sodium hexametaphosphate, potassium dihydrogenphosphate, trisodium phosphate, tripotassium phosphate and mixtures thereof.
- the remineralising phosphate source is a mixture of trisodium phosphate and sodium dihydrogen phosphate.
- the amount of remineralising phosphate source(s) (e.g. trisodium phosphate and sodium dihydrogen phosphate) in the composition of this invention typically ranges from 2 to 15%, preferably from 4 to 10% by total weight remineralising phosphate source based on the total weight of the oral care composition.
- compositions of the present invention may also contain further optional ingredients customary in the art such as anticaries agents, anticalculus agents, buffers, flavouring agents, sweetening agents, colouring agents, opacifying agents, preservatives, antisensitivity agents, antimicrobial agents and the like.
- the invention also provides a process of preparing a non-aqueous oral care composition as defined above, comprising the steps of forming a mixture comprising the thickening agent, the humectant, the liquid polyethylene glycol(s) and the solid polyethylene glycol(s), heating the mixture to a temperature above the melting point of the solid polyethylene glycol(s), and cooling the mixture to form crystals of the solid polyethylene glycol(s).
- a preferred process according of the invention comprises the following steps:
- powdered ingredients such as abrasive cleaning agent and/or surfactant
- ingredients such as the fluoride sources and/or the agents for the remineralisation of teeth, as described above may suitably be added between steps (i) and (ii).
- the following formulation represents a dentifrice composition according to the invention.
- CARBOPOL® 974P NF Polymer (ex Lubrizol 0.3
- the formulation was prepared as follows:
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11725927.5A EP2585031B1 (en) | 2010-06-23 | 2011-06-16 | Non-aqueous oral care compositions |
MX2013004197A MX346376B (en) | 2010-06-23 | 2011-06-16 | Non-aqueous oral care compositions. |
BR112012030590-5A BR112012030590B1 (en) | 2010-06-23 | 2011-06-16 | Non-aqueous Composition for Oral Care and Process for Preparing a Non-aqueous Composition for Oral Care |
CN201180030826.7A CN102946847B (en) | 2010-06-23 | 2011-06-16 | Non-aqueous oral care composition |
US13/704,108 US9877911B2 (en) | 2010-06-23 | 2011-06-16 | Non-aqueous oral care compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10167070.1 | 2010-06-23 | ||
EP10167070 | 2010-06-23 |
Publications (1)
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WO2011160996A1 true WO2011160996A1 (en) | 2011-12-29 |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2011/060003 WO2011160996A1 (en) | 2010-06-23 | 2011-06-16 | Non-aqueous oral care compositions |
Country Status (7)
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US (1) | US9877911B2 (en) |
EP (1) | EP2585031B1 (en) |
CN (1) | CN102946847B (en) |
BR (1) | BR112012030590B1 (en) |
CL (1) | CL2012003664A1 (en) |
MX (1) | MX346376B (en) |
WO (1) | WO2011160996A1 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013033090A1 (en) * | 2011-09-01 | 2013-03-07 | The Procter & Gamble Company | Oral care compositions with improved rheology |
WO2013149830A1 (en) | 2012-04-05 | 2013-10-10 | Unilever N.V. | Non-aqueous oral care composition |
WO2015007503A1 (en) | 2013-07-19 | 2015-01-22 | Unilever Plc | Remineralising oral care products |
WO2015172323A1 (en) * | 2014-05-14 | 2015-11-19 | The Procter & Gamble Company | Oral care compositions having improved stability |
CN105163705A (en) * | 2013-02-14 | 2015-12-16 | 荷兰联合利华有限公司 | Non-aqueous oral care compositions |
WO2016071182A1 (en) | 2014-11-03 | 2016-05-12 | Unilever Plc | Modelling method |
US20160213581A1 (en) * | 2013-09-02 | 2016-07-28 | Glaxo Group Limited | Novel dentifrice composition |
WO2016148946A1 (en) * | 2015-03-18 | 2016-09-22 | Psmg, Llc | Stable polyethylene glycol particle dispersions and methods for forming the stable dispersions |
US10595976B2 (en) | 2015-06-05 | 2020-03-24 | Conopco Inc. | Oral care device |
WO2023180107A1 (en) | 2022-03-24 | 2023-09-28 | Unilever Ip Holdings B.V. | Method for demonstrating efficacy of oral care product |
WO2023180108A1 (en) | 2022-03-24 | 2023-09-28 | Unilever Ip Holdings B.V. | Method for demonstrating efficacy of oral care product |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3128998B1 (en) | 2014-04-10 | 2019-08-07 | Basf Se | Oral care compositions |
WO2023186746A1 (en) | 2022-04-01 | 2023-10-05 | Unilever Ip Holdings B.V. | An oral care composition |
WO2023186648A1 (en) | 2022-04-01 | 2023-10-05 | Unilever Ip Holdings B.V. | An oral care composition |
WO2023186583A1 (en) | 2022-04-01 | 2023-10-05 | Unilever Ip Holdings B.V. | An oral care composition |
WO2024046751A1 (en) * | 2022-08-31 | 2024-03-07 | Unilever Ip Holdings B.V. | Process for the manufacture of a non-aqueous composition |
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Also Published As
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BR112012030590A2 (en) | 2016-08-16 |
CN102946847B (en) | 2016-08-24 |
EP2585031A1 (en) | 2013-05-01 |
EP2585031B1 (en) | 2017-08-30 |
MX346376B (en) | 2017-03-16 |
US20130095045A1 (en) | 2013-04-18 |
CN102946847A (en) | 2013-02-27 |
MX2013004197A (en) | 2013-06-05 |
BR112012030590B1 (en) | 2018-01-23 |
CL2012003664A1 (en) | 2013-06-07 |
US9877911B2 (en) | 2018-01-30 |
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