CN108136222B - 口腔护理组合物 - Google Patents
口腔护理组合物 Download PDFInfo
- Publication number
- CN108136222B CN108136222B CN201580083469.9A CN201580083469A CN108136222B CN 108136222 B CN108136222 B CN 108136222B CN 201580083469 A CN201580083469 A CN 201580083469A CN 108136222 B CN108136222 B CN 108136222B
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- Prior art keywords
- oral care
- care composition
- phosphate
- weight
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 126
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- FSBZGYYPMXSIEE-UHFFFAOYSA-H tin(2+);diphosphate Chemical compound [Sn+2].[Sn+2].[Sn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O FSBZGYYPMXSIEE-UHFFFAOYSA-H 0.000 claims abstract description 17
- 229910001463 metal phosphate Inorganic materials 0.000 claims abstract description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 73
- 239000000377 silicon dioxide Substances 0.000 claims description 34
- -1 fluoride ions Chemical class 0.000 claims description 28
- 229910019142 PO4 Inorganic materials 0.000 claims description 15
- 239000000551 dentifrice Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 235000021317 phosphate Nutrition 0.000 claims description 12
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 239000003906 humectant Substances 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 235000011180 diphosphates Nutrition 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 claims description 6
- 239000011775 sodium fluoride Substances 0.000 claims description 6
- 235000013024 sodium fluoride Nutrition 0.000 claims description 6
- 229920000388 Polyphosphate Polymers 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000001205 polyphosphate Substances 0.000 claims description 5
- 235000011176 polyphosphates Nutrition 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 4
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical class OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 3
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
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- 235000015218 chewing gum Nutrition 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- 239000007937 lozenge Substances 0.000 claims description 2
- 125000005341 metaphosphate group Chemical group 0.000 claims description 2
- 230000002087 whitening effect Effects 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 19
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 6
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 abstract description 3
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 abstract description 3
- 239000004137 magnesium phosphate Substances 0.000 abstract description 3
- 229910000157 magnesium phosphate Inorganic materials 0.000 abstract description 3
- 229960002261 magnesium phosphate Drugs 0.000 abstract description 3
- 235000010994 magnesium phosphates Nutrition 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 16
- 229940024606 amino acid Drugs 0.000 description 15
- 235000001014 amino acid Nutrition 0.000 description 15
- 150000001413 amino acids Chemical class 0.000 description 15
- 239000011734 sodium Substances 0.000 description 13
- 210000003298 dental enamel Anatomy 0.000 description 12
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- 239000003945 anionic surfactant Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 239000000606 toothpaste Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 229940034610 toothpaste Drugs 0.000 description 9
- 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 8
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- 239000000796 flavoring agent Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 7
- 229960002799 stannous fluoride Drugs 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- 239000004475 Arginine Substances 0.000 description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
- 235000009697 arginine Nutrition 0.000 description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 229940091249 fluoride supplement Drugs 0.000 description 6
- 235000013355 food flavoring agent Nutrition 0.000 description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 6
- 229910052770 Uranium Inorganic materials 0.000 description 5
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- 208000002925 dental caries Diseases 0.000 description 5
- 230000003628 erosive effect Effects 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 210000000214 mouth Anatomy 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 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 5
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 208000006558 Dental Calculus Diseases 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
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- 239000000178 monomer Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 201000005581 enamel erosion Diseases 0.000 description 3
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Abstract
一种口腔护理组合物，其包含选自磷酸亚锡、磷酸镁或磷酸铝的至少一种金属磷酸盐；和至少一种氟离子源。将所述至少一种磷酸盐以预先形成的盐的形式加入所述口腔护理组合物中。还公开了将所述口腔护理组合物施用给受试者的方法。
Description
背景技术
牙齿酸蚀涉及由非细菌来源的酸侵袭导致的牙齿结构脱矿化和损伤。酸蚀最初发现在牙釉质中，如果不加以控制，可能会进入下面的牙质。酸性食物和饮料、与氯化游泳池水的接触以及胃酸回流可引起或加剧牙齿酸蚀。
牙釉质是带负电的表面，其自然倾向于吸引带正电的离子如氢离子和钙离子，同时排斥带负电的离子如氟离子。根据周围唾液的相对pH值，牙釉质将失去或获得带正电的离子如钙离子。一般唾液的pH值在7.2与7.4之间。当pH降低时，围绕牙齿的流体介质相对于牙齿矿物相变得不饱和并且牙齿溶解，从而释放钙离子和磷酸根离子。这会损害牙釉质并形成多孔的海绵状粗糙表面。如果唾液在较长时间内保持酸性，则可能不会发生再矿化，并且牙齿将继续失去矿物质，从而导致牙齿变弱并最终失去结构。
诸如锌和亚锡的重金属离子可抵抗酸侵袭。已经证实这些离子会形成不溶性化合物，这些化合物沉积在牙齿表面而形成可保护牙釉质免于酸蚀的膜，如美国专利申请No.2003/0165442中所教导，该专利的公开内容据此以引用方式整体并入本文。此外，亚锡在斑块和龋齿研究中已被证实具有抗微生物特性并且已知可提供抗龈炎益处。
可溶性亚锡盐如氟化亚锡、氯化亚锡、乙酸亚锡、氟化亚锡钠、氟化亚锡钾、六氟锆酸钠、硫酸亚锡、酒石酸亚锡、葡萄糖酸亚锡等已经用于洁齿剂组合物中，但具有缺点。溶液中的亚锡离子带来令人不愉快的发涩口感，因此难以实现提供有效的亚锡水平并且还具有可接受的治疗特性的制剂。此外，游离亚锡离子在水溶液中不稳定。氟化亚锡在水中的不稳定性主要是由于亚锡离子(Sn2+)的反应性。锡在高于4的pH下容易水解，从而导致溶液沉淀，结果丧失治疗特性。
因此，需要提供稳定的亚锡制剂，其可以提供亚锡的一种或多种治疗益处。还希望提供用于治疗或控制牙釉质酸蚀、提高抗微生物效力、减少牙斑或治疗或控制牙龈炎的改进产品。
发明内容
本公开涉及一种口腔护理组合物。所述组合物包含选自磷酸亚锡、磷酸镁或磷酸铝的至少一种金属磷酸盐；和至少一种氟离子源。将所述至少一种磷酸盐以预先形成的盐的形式加入所述口腔护理组合物中。
由下文中所提供的详细说明，本公开的其他适用领域将变得显而易见。应理解的是，虽然详细说明和具体实例指出本公开的优选实施方案，但是这些详细描述和具体实例意图仅达到说明的目的，而无意限制本公开的范围。
具体实施方式
以下对优选实施方案的描述在本质上仅是示例性的，并且决不意图限制本公开、本公开的应用或用途。
如通篇所用，范围用作描述范围内的每个值的简略表达方式。范围内的任何值都可以选为范围终点。另外，本文引用的所有参考文献据此全文以引用方式并入。如果本公开中的定义和所引用参考文献的定义发生冲突，则以本公开为准。
除非另外规定，否则本文和在本说明书中其他处表达的所有百分比和量应理解为是指重量百分比。给定的量是基于材料的有效重量计。
本公开的一个实施方案涉及用于间歇使用(例如日常使用)的呈洁齿剂形式的口腔护理组合物。所述口腔护理组合物包含：选自磷酸亚锡、磷酸镁或磷酸铝的至少一种金属磷酸盐，其中所述至少一种磷酸盐以预先形成的盐的形式加入口腔护理组合物中；和至少一种氟离子源。如本文所用，术语“预先形成的盐”是指磷酸盐不是在口腔护理组合物中原位(例如通过磷酸和亚锡盐的反应)形成。
在一个实施方案中，金属磷酸盐是亚锡、镁或铝的无机磷酸盐。本文使用的“磷酸盐”涵盖口服可接受的单磷酸盐和多磷酸盐，例如，P1-6磷酸盐，例如单体磷酸盐如一元磷酸盐、二元磷酸盐或三元磷酸盐；和二聚磷酸盐如焦磷酸盐；和多聚磷酸盐。在一个实施方案中，金属磷酸盐是无水或水合磷酸亚锡盐，例如三元磷酸亚锡。在一个实施方案中，磷酸盐不是焦磷酸盐、偏磷酸盐或其他多磷酸盐。除了磷酸亚锡以外，还可以使用预先形成的亚锡盐，而不是磷酸亚锡。在另一个实施方案中，所述组合物中使用的唯一预先形成的亚锡化合物是磷酸亚锡。在一个实施方案中，磷酸亚锡化合物不包括有机配体。
可采用任何量的有效保护免于牙釉质酸蚀和/或提供本文所述其他益处的金属磷酸盐。相对于洁齿剂组合物的重量，合适量的金属磷酸盐的实例可以在0.1至10重量％，例如0.2至5重量％，例如0.5至4重量％的范围内。
金属磷酸盐当置于制剂中时，例如在酸性或碱性pH下，可以在使用时充分溶解，以对牙釉质提供有效浓度的金属离子，从而防止酸蚀、减少细菌定殖和生物膜形成，并且对牙齿提供增强的光泽。在一些实施方案中，所述制剂包含氨基酸，例如碱性氨基酸如精氨酸或赖氨酸，其可以赋予制剂碱性pH。
本公开的组合物还包含至少一种氟离子源，例如氟化物盐。可采用多种产氟离子的物质作为本发明组合物中的可溶性氟化物的来源。合适的产氟离子的物质的实例见于授予Briner等人的美国专利No.3,535,421、授予Parran，Jr.等人的美国专利No.4,885,155和授予Widder等人的美国专利Widder等人的美国专利No.3,678,154，其每个的公开内容据此以引用的方式整体并入。代表性氟离子源包括但不限于氟化亚锡、氟化钠、氟化钾、单氟磷酸钠、氟硅酸钠、氟硅酸铵、胺氟化物、氟化铵及其组合。在某些实施方案中，氟离子源包括氟化亚锡和氟化钠、单氟磷酸钠及其混合物。本发明的发明人已经发现与磷酸亚锡组合的这些氟离子源可提供增强的抗微生物和/或抗酸蚀特性。加入至少一种氟离子可潜在地提供一种或多种其他优点，例如减少有害斑块和细菌。
在某些实施方案中，本公开的口腔护理组合物可包含氟离子源或提供氟的成分，所述氟离子源或提供氟的成分的量足以提供25ppm至25,000ppm(质量分数)的氟离子，通常至少500ppm，例如500至2000ppm，例如1000至1600ppm，例如约1450ppm。氟化物的适当含量将取决于特定应用。供一般消费者使用的牙膏将典型地具有1000至1500ppm，其中儿童牙膏略低。供专业人员施加的洁齿剂或涂层可具有多达5,000或甚至25,000ppm的氟化物。氟离子源可基于组合物的总重量计按以下水平添加到本公开的组合物中：在一个实施方案中从0.01重量％至10重量％，或0.03重量％至5重量％，以及在另一个实施方案中0.1重量％至1重量％。用于提供适当水平的氟离子的氟化物盐的重量将基于盐中的抗衡离子的重量而明显地变化。
所述组合物可以任选地包含适用于口腔护理组合物的附加成分。这种成分的实例包括活性剂，例如另外的氟化物源和/或另外的磷酸盐源。可将组合物配制在洁齿剂基料中，例如包含磨料例如二氧化硅磨料、表面活性剂、发泡剂、维生素、聚合物、酶、湿润剂、增稠剂、另外的抗微生物剂、防腐剂、调味剂、着色剂和/或它们的组合。合适的洁齿剂基料的实例在本领域中是已知的。或者，可将组合物配制成凝胶(例如用于牙托中)、口香糖、锭剂或薄荷。以下将更详细地讨论可用于本公开的组合物中的合适的附加成分的实例。
活性剂：本公开的组合物可以包含各种其他活性剂，所述活性剂用于保护和增强牙釉质和牙齿结构的强度和完整性和/或减少细菌和相关的龋齿和/或牙龈疾病。在本文中供使用的活性成分的有效浓度将取决于所使用的特定药剂和递送系统。浓度也将取决于所选择的确切的盐或聚合物。例如，在以盐形式提供活性剂的情况下，抗衡离子将影响盐的重量，以使得如果抗衡离子较重，则将需要以重量计更多的盐来在最终产品中提供相同浓度的活性离子。当存在时，精氨酸可以例如0.1重量％至20重量％(表示为游离碱的重量)的水平存在，例如，针对消费者牙膏来说1重量％至10重量％，或针对专业或处方治疗产品来说，7重量％至20重量％。在一个实施方案中，三氯生牙膏可包含0.1重量％至1重量％，例如约0.3重量％三氯生。
氨基酸：在一些实施方案中，本公开的组合物包含氨基酸。在特定的实施方案中，氨基酸可以是碱性氨基酸。所谓“碱性氨基酸”是指天然存在的碱性氨基酸诸如精氨酸、赖氨酸和组氨酸，以及分子中具有羧基和氨基的任何碱性氨基酸，所述碱性氨基酸是水溶性的并提供pH为7或更大的水溶液。因此，碱性氨基酸包括但不限于精氨酸、赖氨酸、瓜氨酸、鸟氨酸、肌氨酸、组氨酸、二氨基丁酸、二氨基丙酸、其盐和/或其组合。在一个特定实施方案中，碱性氨基酸选自精氨酸、瓜氨酸和鸟氨酸。在某些实施方案中，碱性氨基酸是精氨酸，例如L-精氨酸或其盐。在其他实施方案中，氨基酸被季铵化，例如氨基另外被取代形成季铵部分，其可以与羧基形成内盐，例如甜菜碱(N，N，N-三甲基甘氨酸)。
在各种实施方案中，在洁齿剂的情况下，氨基酸的存在量为总组合物重量的0.5重量％至20重量％、总组合物重量的0.5重量％至10重量％，例如总组合物重量的1.5重量％、3.75重量％、5重量％或7.5重量％。
磨料：本公开的组合物可包含磨料，所述磨料可包括任何合适的二氧化硅磨料，例如标准清洁二氧化硅、高清洁二氧化硅和/或其他磨料二氧化硅。其他合适的附加磨料包括例如磷酸钙磨料，例如磷酸三钙(Ca3(PO4)2)、羟磷灰石(Ca10(PO4)6(OH)2)或二水磷酸二钙(CaHPO4·2H2O，有时在本文也称为DiCal)或焦磷酸钙；碳酸钙磨料；或磨料如偏磷酸钠、偏磷酸钾、硅酸铝、煅烧氧化铝、膨润土或其他硅质材料，或其组合。
本文中适用的二氧化硅磨料抛光材料以及其他磨料通常具有在0.1微米与30微米之间，例如在5微米与15微米之间的范围内的平均粒度。二氧化硅磨料可来自沉淀二氧化硅或二氧化硅凝胶，诸如在授予Pader等人的美国专利No.3,538,230和授予Digiulio的美国专利No.3,862,307中描述的二氧化硅干凝胶，这些专利的公开内容以引用的方式整体并入本文。特定的二氧化硅干凝胶由W.R.Grace & Co.Davison Chemical Division以商标名
出售。沉淀二氧化硅材料包括由J.M.Huber Corp.以商标名
出售的那些，包括带有标示Zeodent 115和119的二氧化硅。这些二氧化硅磨料在授予Wason的美国专利No.4,340,583中有描述，该专利的公开内容以引用的方式整体并入本文。在某些实施方案中，适用于根据本公开的口腔护理组合物的实践的磨料材料包括二氧化硅凝胶和沉淀非晶形二氧化硅，其具有小于100cc/100g二氧化硅并且在45cc/100g二氧化硅至70cc/100g二氧化硅范围内的吸油值。吸油值使用ASTARub-Out Method(擦掉法)D281来测量。在某些实施方案中，二氧化硅是具有3微米至12微米和5微米至10微米的平均粒度的胶态颗粒。特别适用于本公开的实践的低吸油量二氧化硅磨料以商标名Sylodent
由W.R.Grace &Co.，Baltimore，Md.21203的Davison Chemical Division销售。Sylodent 650
是适用于本公开的实践的低吸油量二氧化硅磨料的实例，其为由胶态二氧化硅的颗粒构成的二氧化硅水凝胶，所述颗粒具有的水含量29重量％，直径平均为7微米至10微米，并且吸油量低于70cc/100g二氧化硅。在某些实施方案中，二氧化硅是具有3微米至12微米和5微米至10微米的平均粒度的胶态颗粒。尤其适用于本发明的实践的低吸油量二氧化硅磨料以商标名Sylodent
由W.R.Grace & Co.，Baltimore，Md.21203的Davison ChemicalDivision销售。Sylodent 650
是适用于本发明的实践的低吸油量二氧化硅磨料的实例，其为由胶态二氧化硅的颗粒构成的二氧化硅水凝胶，所述颗粒具有的水含量为29重量％，直径平均为7微米至10微米，并且吸油量低于70cc/100g二氧化硅。
可采用任何合适量的二氧化硅磨料。合适量的实例包括基于组合物的总重量计5重量％或更多干重的二氧化硅颗粒，例如5重量％至40重量％，或15重量％至30重量％或15重量％至25重量％。
发泡剂：本公开的口腔护理组合物还可包含当刷动口腔时增加所产生的泡沫的量的试剂。增加泡沫量的试剂的说明性实例包括但不限于聚氧乙烯和某些聚合物，包括但不限于海藻酸盐聚合物。聚氧乙烯可增加由本公开的口腔护理组合物所产生的泡沫的量和泡沫的浓密程度。聚氧乙烯也通常被称为聚乙二醇(“PEG”)或聚氧化乙烯。适合于本公开组合物的聚氧乙烯将具有200,000至7,000,000的分子量。在一个实施方案中，分子量将为600,000至2,000,000，以及在另一个实施方案中800,000至1,000,000。
是由UnionCarbide生产的高分子量聚氧乙烯的商标名。基于本公开的口腔护理组合物的重量计，发泡剂(例如聚氧乙烯)的存在量可以为0.1％至50％，在一个实施方案中为0.5％至20％，在另一个实施方案中为1％至10％，或2％至5％。
表面活性剂：本公开的组合物可包含阴离子表面活性剂，例如：
i.高级脂肪酸单硫酸单甘油酯的水溶性盐，诸如氢化椰子油脂肪酸的单硫酸化单甘油酯的钠盐，诸如N-甲基N-椰油基牛磺酸钠、椰油酸单甘油酯硫酸钠，
ii高级烷基硫酸盐，诸如月桂基硫酸钠，
iii.高级烷基醚硫酸盐，例如，式CH3(CH2)mCH2(OCH2CH2)nOSO3X的高级烷基醚硫酸盐，其中m为6-16，例如10，n为1-6，例如2、3或4，并且X为Na或K，例如月桂基聚氧乙烯(2)醚硫酸钠(CH3(CH2)10CH2(OCH2CH2)2OSO3Na)，
iv.高级烷基芳基磺酸盐，诸如月桂基苯磺酸钠(月桂基苯磺酸钠)，
v.高级烷基磺基乙酸盐，如月桂基磺基乙酸钠(月桂基磺基乙酸钠)、1，2二羟基丙烷磺酸的高级脂肪酸酯、磺基月桂酸盐(sulfocolaurate)(N-2-乙基月桂酸钾磺基乙酰胺)和月桂基肌氨酸钠。
“高级烷基”意思是例如C6-30烷基。在特定实施方案中，阴离子表面活性剂选自月桂基硫酸钠和月桂基醚硫酸钠。阴离子表面活性剂可以有效的(例如，大于配方的0.01重量％)，但不处于将刺激口腔组织的浓度下(例如，小于10％)的量存在，并且最佳浓度取决于特定配方和特定表面活性剂。在一个实施方案中，阴离子表面活性剂以0.3重量％至4.5重量％(例如，约1.5重量％)存在于牙膏中。本公开的组合物可任选地包含表面活性剂的混合物，例如，包含阴离子表面活性剂和可为阴离子、阳离子、两性离子或非离子的其他表面活性剂。通常，合适的表面活性剂是在宽的pH范围内合理稳定的那些表面活性剂。表面活性剂更全面地例如在授予Agricola等人的美国专利No.3,959,458、授予Haefele的美国专利No.3,937,807和授予Gieske等人的美国专利No.4,051,234进行了描述，这些专利的公开内容以引用的方式整体并入本文。在某些实施方案中，适用于本文中的阴离子表面活性剂包括在烷基中具有10至18个碳原子的烷基硫酸酯的水溶性盐以及具有10至18个碳原子的脂肪酸的磺化单甘油酯的水溶性盐。月桂基硫酸钠、月桂酰肌氨酸钠以及椰子基单甘油酯磺酸钠为这一类型的阴离子表面活性剂的实例。在一个特定实施方案中，所述组合物包含月桂基硫酸钠。在某些实施方案中，适用于本文中的阴离子表面活性剂包括在烷基中具有10至18个碳原子的烷基硫酸酯的水溶性盐以及具有10至18个碳原子的脂肪酸的磺化单甘油酯的水溶性盐。月桂基硫酸钠、月桂酰肌氨酸钠以及椰子基单甘油酯磺酸钠为这一类型的阴离子表面活性剂的实例。在一个实施方案中，所述组合物包含月桂基硫酸钠。
除阴离子表面活性剂之外并入的表面活性剂或相容表面活性剂的混合物可以基于总组合物的重量计以0.1％至5.0％，在另一个实施方案中0.3％至3.0％，以及在另一个实施方案中0.5％至2.0％存在于本公开的组合物中。这些范围不包括阴离子表面活性剂的量。
在一个实施方案中，本公开的组合物包含两性离子表面活性剂，例如甜菜碱表面活性剂，例如椰油酰胺丙基甜菜碱，其量为0.1重量％至4.5重量％，例如0.5％至2％的椰油酰胺丙基甜菜碱。
牙垢控制剂：在本公开的各种实施方案中，所述组合物包含抗牙结石(牙垢控制)剂。合适的抗牙结石剂非限制地包括磷酸盐和聚磷酸盐(例如焦磷酸盐)、聚氨基丙磺酸(AMPS)、六偏磷酸盐、柠檬酸锌三水合物、多肽、聚烯烃磺酸盐、聚烯烃磷酸盐和二磷酸盐。因此，本公开内容除了磷酸亚锡以外还可以包含磷酸盐。在特定实施方案中，这些盐是碱金属磷酸盐，例如碱金属氢氧化物或碱土金属氢氧化物的盐，例如钠盐、钾盐或钙盐(例如六偏磷酸钠)。这里使用的“磷酸盐”如上所定义。在具体的实例中，磷酸盐选自碱金属磷酸氢盐和碱金属焦磷酸盐，例如选自磷酸氢二钠、磷酸氢二钾、磷酸二钙二水合物、焦磷酸钙、焦磷酸四钠、焦磷酸四钾、三聚磷酸钠，以及其中任何两种或更多种的混合物。在一个特定实施方案中，例如所述组合物包含焦磷酸四钠(Na4P2O7)，焦磷酸钙(Ca2P2O7)和磷酸氢二钠(Na2HPO4)的混合物，例如量为3重量％至4重量％的磷酸氢二钠和0.2重量％至1重量％的每种焦磷酸盐。在另一个实施方案中，所述组合物包含焦磷酸四钠(TSPP)和三聚磷酸钠(STPP)(Na5P3O10)的混合物，例如比例为基于所述组合物的重量计0.5重量％至5重量％例如1重量％至2重量％的TSPP与7％至10％的STPP。以有效减少牙釉质的酸蚀以有助于清洁牙齿和/或减少牙齿上的牙垢积聚的量，例如0.2重量％至20重量％如1重量％至15重量％的量提供此类磷酸盐。
调味剂：本公开的口腔护理组合物也可包含调味剂。用于本公开的实践中的调味剂包括但不限于精油以及各种调味醛、酯、醇以及类似物质。精油的实例包括留兰香、胡椒薄荷、冬青、黄樟、三叶草、鼠尾草、桉树、牛至属植物、肉桂、柠檬、酸橙、柚子和橙的油。诸如薄荷醇、香芹酮以及茴香脑等化学品也适用。某些实施方案采用薄荷油和绿薄荷油。调味剂可以按0.1重量％至5重量％和0.5重量％至1.5重量％的浓度掺入口腔组合物中。
聚合物：本公开的口腔护理组合物还可以包含另外的聚合物以调节配方的粘度或增强其他成分的溶解性。此类另外的聚合物包括聚乙二醇、多糖(例如纤维素衍生物，例如羧甲基纤维素、微晶纤维素或多糖胶，例如黄原胶或角叉菜胶)。酸性聚合物(例如聚丙烯酸酯凝胶)可以其游离酸或者部分或完全中和的水溶性碱金属(例如钾和钠)或铵盐的形式提供。
在水性介质中形成聚合物结构或凝胶的二氧化硅增稠剂可以存在。注意，这些二氧化硅增稠剂在物理和功能上有别于也存在于组合物中的微粒二氧化硅磨料，因为二氧化硅增稠剂非常精细地分散并提供极少作用或无研磨作用。其他增稠剂为羧基乙烯基聚合物、角叉菜胶、羟乙基纤维素和纤维素醚的水溶性盐，诸如羧甲基纤维素钠和羧甲基羟乙基纤维素钠。也可将天然胶诸如刺梧桐胶、阿拉伯树胶和黄芪胶掺入。胶态硅酸镁铝也可用作增稠组合物的组分以便进一步改善组合物的质地。在某些实施方案中，使用基于总组合物的重量计0.5％至5.0％的量的增稠剂。
本公开的组合物可以包含阴离子聚合物，例如其量为0.05％至5％。通常已知用于洁齿剂中的此类试剂的实例公开于美国专利No.5,188,821和5,192,531中，这些专利的公开内容以引用的方式整体并入本文；并且包括合成的阴离子聚合聚碳酸酯，诸如马来酸酐或马来酸与另一可聚合烯属不饱和单体的1∶4至4∶1共聚物，优选具有30,000至1,000,000例如300,000至800,000的分子量(M.W.)的甲基乙烯基醚/马来酸酐。这些共聚物可例如作为Gantrez获得，例如，可得自ISP Technologies，Inc.，Bound Brook，N.J.08805的AN 139(M.W.500,000)、AN 119(M.W.250,000)和优选的S-97药物级(M.W.700,000)。增强剂当存在时以0.05重量％至3重量％的量存在。其他起作用的聚合物包括诸如马来酸酐与丙烯酸乙酯、甲基丙烯酸羟乙酯、N-乙烯基-2-吡咯烷酮或乙烯的1∶1共聚物的那些，后者可例如以Monsanto EMA编号1103、M.W.10,000以及EMA等级61获得；以及丙烯酸与甲基丙烯酸甲酯或甲基丙烯酸羟乙酯、丙烯酸甲酯或丙烯酸乙酯、异丁基乙烯醚或N-乙烯基-2-吡咯烷酮的1∶1共聚物。一般来讲，适合的是包含活性碳-碳烯属双键和至少一个羧基的聚合的烯属或烯系不饱和羧酸，即包含因为在相对于羧基的α-β位置中或作为未端亚甲基群组的一部分存在于单体分子中而容易在聚合中起作用的烯属双键的酸。此类酸的例证为丙烯酸、甲基丙烯酸、乙基丙烯酸、α-氯代丙烯酸、巴豆酸、β-丙烯酰氧基丙酸、山梨酸、α-氯代山梨酸、肉桂酸、β-苯乙烯基丙烯酸、粘糠酸、衣康酸、柠康酸、中康酸、戊烯二酸、乌头酸、α-苯基丙烯酸、2-苯甲基丙烯酸、2-环己基丙烯酸、当归酸、伞形酸、富马酸、马来酸以及酸酐。可与此类含羧基单体共聚的其他不同的烯属单体包括乙烯基乙酸酯、氯乙烯、马来酸二甲酯等。共聚物包含对于水溶性来讲足够的含羧基盐基团。另一类聚合剂包括包含取代丙烯酰胺的均聚物和/或不饱和磺酸及其盐的均聚物的组合物，特别地其中聚合物是分子量为1,000至2,000,000的基于选自丙烯酰胺基烷基磺酸(诸如2-丙烯酰胺2甲基丙烷磺酸)的不饱和磺酸，其在授予Zahid的1989年6月27日的美国专利No.4,842,847中有所描述，该专利的公开内容以引用的方式整体并入本文。另一类适用的聚合剂包括包含成比例的阴离子表面活性氨基酸的聚氨基酸，诸如天冬氨酸、谷氨酸和磷酸丝氨酸，例如，如颁发给Sikes等人的美国专利No.4,866,161中公开的那些，该专利的公开内容以引用的方式整体并入本文。
水：口腔组合物可以包含显着水平的水，例如基于组合物的总重量计超过10重量％，例如15重量％至70重量％或20重量％至50重量％。商业口腔组合物的制备中采用的水可以为去离子的(有时也称为软化水)并且不包含机杂质。组合物中该量的水包括所添加的游离水加上与其他材料一起引入的量的水。
湿润剂：在口腔组合物的某些实施方案内，掺入湿润剂来防止组合物在暴露于空气之后硬化也是合乎需要的。某些湿润剂也可将合乎需要的甜味或风味赋予洁齿剂组合物。适合的湿润剂包括可食用的多羟基醇，诸如甘油、山梨糖醇、木糖醇、丙二醇以及其他多元醇和这些湿润剂的混合物。在本公开的一个实施方案中，主要湿润剂是甘油、山梨糖醇或其组合中的一种。保湿剂可以基于组合物的总重量计以大于25重量％，例如25重量％至55重量％，或30重量％至50重量％的水平存在。
其他任选成分：除上述组分之外，本公开的实施方案还可以包含多种任选的洁齿剂成分，其中一些在下文描述。任选的成分包括例如但不限于粘合剂、起泡剂、调味剂、甜味剂，例如糖精钠、另外的抗牙斑剂、磨料、美观剂例如TiO2包覆的云母或其他着色剂。这些和其他任选的组分在授予Majeti的美国专利No.5,004,597、授予Agricola等人的美国专利No.3,959,458和授予Haefele的美国专利No.3,937,807中有进一步描述，所有这些专利均以引用方式并入本文。
在一个实施方案中，本公开的组合物基本上不含或不包含以下成分中的任何一种或多种：酰基肌氨酸酯或其盐，例如月桂酰肌氨酸钠、椰油酰肌氨酸钠、肉豆蔻酰肌氨酸钠、月桂酰肌氨酸TEA盐、椰油酰肌氨酸铵、月桂酰肌氨酸铵；抗氧化剂，如没食子酸丙酯、丁基化羟基茴香醚(BHA)、丁基化羟基甲苯(BHT)、乙基香草醛、迷迭香油、卵磷脂、维生素E、芦丁、桑色素、非瑟酮和其他生物类黄酮；植酸化合物，其在本文中定义为包括植酸及其盐，例如碱金属或碱土金属盐和植酸钙镁，以及肌肉-肌醇五磷酸及其盐；乙二胺四乙酸盐；熔融石英；交联的聚乙烯吡咯烷酮增稠剂；选自硝酸钾、柠檬酸钾、氯化钾、碳酸氢钾和草酸钾的钾盐脱敏剂；含铜化合物，例如铜盐或选自硫酸铜、卤化铜和拟卤化物的释放铜离子的其他铜化合物、硝酸铜、同系列甲酸至癸酸中的羧酸的铜盐、系列草酸至辛二酸中的多元酸的铜盐、选自乙醇酸、乳酸、酒石酸、苹果酸和柠檬酸的羟基羧酸的铜盐、在固体或胶体载体上沉淀的铜、例如选自以下的载体：二氧化硅、粘土、生物聚合物和合成聚合物，以及铜水滑石；或可以呈颗粒形式的聚有机倍半硅氧烷，例如聚甲基倍半硅氧烷。术语“基本上不含”在本文中定义为基于组合物的总重量计小于0.01重量％。
本申请还公开了使用本文所述的组合物来提高牙釉质中的亚锡水平，以及治疗、减少或控制牙釉质酸蚀发生的方法，其包括将本文所述的任何组合物例如通过刷涂施用于牙齿。在各种实施方案中，本公开提供了一种方法，其用于(i)降低牙齿的超敏，(ii)减少牙斑累积，(iii)减少或抑制脱矿化和促进牙齿的再矿化，(iv)抑制口腔中的微生物生物膜形成，(v)减少或抑制齿龈炎，(vi)促进嘴部中疱疹或割口的愈合，(vii)降低产酸细菌的水平，(viii)增加非龋齿和/或非牙斑形成细菌的相对水平，(ix)减少或抑制龋齿的形成，(x)减少、修补或抑制牙釉质的龋齿前(pre-carious)病灶，例如，如通过定量光诱导荧光(QLF)或电气龋齿测量法(ECM)所检测的，(xi)治疗、缓解或减少口干，(xii)清洁牙齿和口腔，(xiii)减少酸蚀，(xiv)美白牙齿；(xv)减少牙垢积聚和，和/或(xvi)促进全身健康，包括心血管健康，例如，通过减少经由口腔组织引起全身性感染的可能性来促进，所述方法包括例如通过用本公开的任何组合物每天刷牙一次或多次来将如上所述的任何组合物施用于有需要的人的口腔。本公开进一步提供了用于这些方法中的任何一种的组合物。
实施例
实施例1-洁齿剂制剂
如表1所示，根据实施例1的下列配方制备包含1％磷酸亚锡与0.243％氟化钠组合的测试洁齿剂。还制备了表1中实施例2和比较例A的制剂。列出的成分量以组合物的重量计。
表1
实施例2
如下评估实施例1和比较例A的制剂的功效：
1.从4名健康志愿者采集牙斑，并且汇合在一起作为接种物。使接种物的光密度(“O.D.’)与在610nm处的0.3吸光度相匹配。
2.将ACTA盖子上的无菌竖直羟磷灰石(“HAP”)圆盘在37℃下在厌氧条件下与1ml无菌人工唾液(具有0.01％蔗糖)和1ml汇合唾液一起在24孔微板中温育24小时。使用ACTA盖子来对所有的孔进行同时处理。
3.将新鲜制备的处理溶液(1份在测试的实施例的牙膏对应于2份无菌蒸馏水)添加至孔中，并且使其与HAP圆盘接触10分钟。
4.用2ml无菌磷酸盐缓冲盐水(“PBS”)替换浆液并使其接触1分钟。
5.移除液相，并且用2ml无菌人工唾液替换。
6.对于对照和测试洁齿剂，将圆盘一式三份地处理8天。
7.在2、4和8天的间隔下，无菌收集圆盘，并转移至强度被预先降低一半的巯基乙醇酸盐培养基中。
8.将各圆盘的100ml 10-4稀释物、10-5稀释物和10-6稀释物一式两份地涂铺在新霉素-万古霉素(NV)琼脂和羊血琼脂上以测定总革兰氏阴性厌氧菌和总厌氧细菌。
9.使用无菌涂布器涂布各板表面，并且在37℃下厌氧温育72小时，随后对菌落计数。
10.使用液相对整个研究周期监测pH。
在下表2中以log 10降低值来记录平板计数。单位为平均Log 10CFU/ml，其中平均值是基于针对每个实施例制剂测试的样品数量来计算。
表2
| 新霉素万古霉素琼脂 | 第8天 | |
| 实施例1 | 含磷酸亚锡的牙膏 | 4.2 |
| 比较例A | 含云母/磷酸锌的牙膏和氟化亚锡牙膏 | 4.22 |
| 比较例B | 不含金属盐的牙膏 | 4.45 |
如表1和2所示，比较例A采用与实施例1中所用类似的基础牙膏配方，但采用磷酸锌和氟化亚锡来代替磷酸亚锡。比较例B是不含金属盐的牙膏形式。如表2中报道的结果所示，与比较例A和比较例B的制剂相比，含有磷酸亚锡的实施例1的制剂提供了改善的抗微生物活性。
实施例3-稳定性数据
对实施例1和2以及比较例A的制剂进行稳定性测试。提供每种制剂的三个样品。将每种制剂的样品在不同的温度下(包括在室温(约25℃)、40℃和49℃下)保持3个月。在研究开始时测量每个样品的初始氟浓度，然后在每个月研究后定期测量。结果表明实施例1和比较例A制剂的氟化物源对于商业应用而言足够稳定，其中实施例1的制剂与比较例A的制剂相比略加稳定。发现实施例2的制剂与实施例1的制剂相比稳定性较低。
Claims (14)
1.一种口腔护理组合物，其包含：
至少一种金属磷酸盐，其中所述至少一种金属磷酸盐是量为0.5重量%至4.0重量%的磷酸亚锡，其中磷酸亚锡以预先形成的盐的形式加入所述口腔护理组合物中，
其中所述磷酸盐不是焦磷酸盐、偏磷酸盐或其他多磷酸盐；和
至少一种氟离子源，其包括氟化钠，其中所述氟化钠以0.1重量%至1.0重量%的量存在。
2.根据权利要求1所述的口腔护理组合物，其还包含磨料。
3.根据权利要求1所述的口腔护理组合物，其进一步包含一种或多种湿润剂和一种或多种表面活性剂。
4.根据权利要求1所述的口腔护理组合物，其还包含效量的不同于所述至少一种金属磷酸盐的一种或多种碱金属磷酸盐。
5.根据前述权利要求中任一项所述的口腔护理组合物，其还包含增白剂。
6.根据权利要求1所述的口腔护理组合物，前提条件是所述口腔护理组合物不含酰基肌氨酸酯或其盐、抗氧化剂、植酸化合物、含铜化合物、乙二胺四乙酸盐和聚有机倍半硅氧烷。
7.根据权利要求1所述的口腔护理组合物，其中所述口腔护理组合物为洁齿剂。
8.根据权利要求1所述的口腔护理组合物，其中所述口腔护理组合物包含：
0.5重量%至4.0重量%的磷酸亚锡；
1重量%至8重量%的碱金属磷酸盐，其选自磷酸氢二钠、磷酸氢二钾、磷酸二钙二水合物以及其中任何两种或更多种的混合物；
0.1重量%至1.0重量%的氟化钠；和
二氧化硅磨料洁齿剂基料。
9.根据权利要求1所述的口腔护理组合物，其中所述口腔护理组合物为凝胶。
10.根据权利要求1所述的口腔护理组合物，其中所述口腔护理组合物为锭剂的形式。
11.根据权利要求1所述的口腔护理组合物，其中所述口腔护理组合物为口香糖。
12.根据权利要求1所述的口腔护理组合物，其还包含效量的一种或多种抗微生物剂。
13.根据权利要求1所述的口腔护理组合物，其中所述组合物的pH为酸性的。
14.根据权利要求1所述的口腔护理组合物，其中所述组合物的pH为碱性的。
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| PCT/US2015/054791 WO2017062020A1 (en) | 2015-10-08 | 2015-10-08 | Oral care compositions |
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| EP (1) | EP3349859B1 (zh) |
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| BR (1) | BR112018006201B1 (zh) |
| CA (1) | CA2979552A1 (zh) |
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| EP3883529A1 (en) | 2018-12-26 | 2021-09-29 | Colgate-Palmolive Company | Oral care compositions |
| CN114288208A (zh) * | 2022-02-22 | 2022-04-08 | 克劳丽化妆品股份有限公司 | 一种牙齿美白组合物、口腔护理清洁用品及其制备方法 |
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- 2015-10-08 US US15/766,517 patent/US20180289599A1/en not_active Abandoned
- 2015-10-08 CA CA2979552A patent/CA2979552A1/en active Pending
- 2015-10-08 EP EP15784529.8A patent/EP3349859B1/en active Active
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| GB845611A (en) * | 1957-01-15 | 1960-08-24 | Hedley Thomas & Co Ltd | Improvements in and relating to toothpastes |
| CN1420757A (zh) * | 1999-11-12 | 2003-05-28 | 宝洁公司 | 亚锡口腔组合物 |
| CN104768520A (zh) * | 2012-11-05 | 2015-07-08 | 宝洁公司 | 热处理的沉淀二氧化硅 |
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| Publication number | Publication date |
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| MX2018003773A (es) | 2018-06-18 |
| CN108136222A (zh) | 2018-06-08 |
| AU2015411327B2 (en) | 2019-05-30 |
| RU2018112161A3 (zh) | 2019-10-07 |
| IL258305A (en) | 2018-05-31 |
| EP3349859A1 (en) | 2018-07-25 |
| EP3349859B1 (en) | 2020-09-23 |
| CA2979552A1 (en) | 2017-04-13 |
| ZA201801038B (en) | 2021-08-25 |
| RU2018112161A (ru) | 2019-10-07 |
| RU2732396C2 (ru) | 2020-09-16 |
| AU2015411327A1 (en) | 2018-04-19 |
| WO2017062020A1 (en) | 2017-04-13 |
| BR112018006201A2 (pt) | 2018-10-09 |
| US20180289599A1 (en) | 2018-10-11 |
| MX382007B (es) | 2025-03-13 |
| BR112018006201B1 (pt) | 2021-03-16 |
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