CN107847405A - 口腔护理组合物 - Google Patents
口腔护理组合物 Download PDFInfo
- Publication number
- CN107847405A CN107847405A CN201580081667.1A CN201580081667A CN107847405A CN 107847405 A CN107847405 A CN 107847405A CN 201580081667 A CN201580081667 A CN 201580081667A CN 107847405 A CN107847405 A CN 107847405A
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- CN
- China
- Prior art keywords
- oral care
- weight
- care composition
- zinc
- composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 218
- 239000004094 surface-active agent Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 7
- 229940006486 zinc cation Drugs 0.000 claims abstract description 6
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 5
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 210000000214 mouth Anatomy 0.000 claims description 39
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 37
- 239000011701 zinc Substances 0.000 claims description 36
- 229910052725 zinc Inorganic materials 0.000 claims description 36
- -1 Zn (II) cation Chemical group 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 241000894006 Bacteria Species 0.000 claims description 17
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 208000007565 gingivitis Diseases 0.000 claims description 11
- 201000001245 periodontitis Diseases 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000551 dentifrice Substances 0.000 claims description 9
- 208000002064 Dental Plaque Diseases 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- 230000007406 plaque accumulation Effects 0.000 claims description 6
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 claims description 6
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 235000005979 Citrus limon Nutrition 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
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- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- CLWNPUARORRDFD-UHFFFAOYSA-N 2-hydroxybutanedioic acid;zinc Chemical compound [Zn].OC(=O)C(O)CC(O)=O CLWNPUARORRDFD-UHFFFAOYSA-N 0.000 claims description 2
- 244000131522 Citrus pyriformis Species 0.000 claims description 2
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
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- 235000005074 zinc chloride Nutrition 0.000 claims description 2
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- 239000011576 zinc lactate Substances 0.000 claims description 2
- 235000000193 zinc lactate Nutrition 0.000 claims description 2
- 229940050168 zinc lactate Drugs 0.000 claims description 2
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 2
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 2
- VRGNUPCISFMPEM-ZVGUSBNCSA-L zinc;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Zn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VRGNUPCISFMPEM-ZVGUSBNCSA-L 0.000 claims description 2
- 244000248349 Citrus limon Species 0.000 claims 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 claims 1
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- VDGJOQCBCPGFFD-UHFFFAOYSA-N oxygen(2-) silicon(4+) titanium(4+) Chemical compound [Si+4].[O-2].[O-2].[Ti+4] VDGJOQCBCPGFFD-UHFFFAOYSA-N 0.000 claims 1
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- 239000011670 zinc gluconate Substances 0.000 claims 1
- 235000011478 zinc gluconate Nutrition 0.000 claims 1
- 229960000306 zinc gluconate Drugs 0.000 claims 1
- 235000016804 zinc Nutrition 0.000 description 32
- 239000003795 chemical substances by application Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 11
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- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 6
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
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- 229910052708 sodium Inorganic materials 0.000 description 6
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- PLXBWHJQWKZRKG-UHFFFAOYSA-N Resazurin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3[N+]([O-])=C21 PLXBWHJQWKZRKG-UHFFFAOYSA-N 0.000 description 4
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- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
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- ZVVSSOQAYNYNPP-UHFFFAOYSA-N olaflur Chemical compound F.F.CCCCCCCCCCCCCCCCCCN(CCO)CCCN(CCO)CCO ZVVSSOQAYNYNPP-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明提供了一种包含具有下式的表面活性剂的口腔护理组合物[R(OC2H4)xOSO3]2M其中R为具有8‑30个碳原子的烷基链长的饱和或不饱和烷基；x为0至10；并且M是选自锌阳离子、铜阳离子和亚锡阳离子的二价金属阳离子。
Description
背景技术
本发明涉及包含金属阳离子的口腔护理组合物，并且特别涉及包含锌、铜和亚锡阳离子的口腔护理组合物。本发明还涉及此类组合物用于口腔护理的用途，以及使用此类组合物的方法。
诸如锌、铜和亚锡的金属阳离子可用在口腔护理组合物中以提供口腔护理益处，诸如抗菌和抑菌活性，以及对抗牙斑和牙龈炎。然而，包含金属阳离子的口腔护理组合物可能遭受负面的味道问题。具体而言，某些消费者可能发现包含金属阳离子的口腔护理组合物是味涩的。
因此希望能够配制包含有益金属阳离子的口腔护理组合物，该组合物不会遭受过度的味道问题。
发明内容
现在已令人惊讶地发现，将烷基硫酸盐表面活性剂形式的金属阳离子掺入口腔护理组合物中可以在比传统金属化合物更低的掺入水平下提供治疗有用水平的金属组分。因此，任何负面的味道影响得以降低。
根据本发明的第一方面，提供了一种口腔护理组合物，其包含具有下式的表面活性剂：
[R(OC2H4)xOSO3]2M
其中
R为具有8-30个碳原子的烷基链长的饱和或不饱和烷基；
x为0至10；并且
M是选自锌阳离子、铜阳离子和亚锡阳离子的二价金属阳离子。
任选地，表面活性剂按组合物的总重量计以0.10重量％至10.0重量％的量存在。
任选地，R是具有10至18个碳原子的饱和或不饱和烷基。进一步任选地，R是具有10至18个碳原子的饱和烷基。
任选地，x为1至4。
任选地，R为具有11个碳原子的饱和烷基，并且x为3。
任选地，口腔护理组合物包含表面活性剂化合物的混合物，所述表面活性剂化合物具有10-16个碳原子的平均烷基链长。
任选地，口腔护理组合物包含具有1至4的x平均值的表面活性剂化合物的混合物。进一步任选地，口腔护理组合物包含具有10-16个碳原子的平均烷基链长和1-4的x平均值的表面活性剂化合物的混合物。
任选地，M是Zn(II)阳离子。
任选地，口腔护理组合物按组合物的总重量计包含0.01重量％至1.0重量％的M。进一步任选地，口腔护理组合物按组合物的总重量计包含0.01重量％至0.80重量％的M。进一步任选地，口腔护理组合物按组合物的总重量计包含0.01重量％至0.75重量％的M、0.01重量％至0.60重量％的M、0.01重量％至0.50重量％的M或0.02重量％至0.20重量％的M。
任选地，口腔护理组合物包含椰油醇硫酸酯锌或椰油醇聚醚硫酸酯锌。进一步任选地，口腔护理组合物包含椰油醇聚醚硫酸酯锌。
任选地，口腔护理组合物还包含口腔可接受的媒介物。
任选地，组合物为洁齿剂或漱口水的形式。
任选地，组合物还包含氟离子源。
任选地，组合物还包含选自柠檬酸锌、硫酸锌、氧化锌、氟化锌、氯化锌、乳酸锌、葡萄糖酸锌、苹果酸锌、酒石酸锌、碳酸锌、磷酸锌及其混合物的锌离子源。
任选地，组合物还包含不含锌的阴离子表面活性剂。进一步任选地，组合物还包含月桂基硫酸钠。
任选地，口腔护理组合物还包含二氧化硅。
可选地，口腔护理组合物还包含多磷酸盐。
任选地，组合物为洁齿剂，其包含：
0.10重量％至10.0重量％的椰油醇聚醚硫酸酯锌；和
0.05重量％至5.0重量％的月桂基硫酸钠。
根据本发明的另一方面，提供了一种用于以下项的方法：
(i)治疗牙龈炎和/或牙周炎，
(ii)减少牙斑积聚和/或
(iii)减少受试者口腔中的细菌，
所述方法包括将根据任一项前述权利要求所述的组合物施用于受试者的口腔。
根据本发明的另一方面，还提供了一种用于以下项的方法中的组合物：
(i)治疗牙龈炎和/或牙周炎，
(ii)减少牙斑积聚和/或
(iii)减少受试者口腔中的细菌，
所述方法包括将组合物施用于受试者的口腔。
根据本发明的另一方面，还提供了组合物用于以下项的用途：
(i)治疗牙龈炎和/或牙周炎，
(ii)减少牙斑积聚和/或
(iii)减少受试者口腔中的细菌。
本发明的其他适用领域从下文提供的详细说明中将变得显而易见。应了解，详细说明和特定实例虽然指示本发明的优选实施方案，但旨在仅用于说明的目的而无意限制本发明的范围。
附图说明
从详细说明和附图中将更全面地理解本发明，其中：
图1说明了根据本发明的组合物对细菌代谢/活力的影响。
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发明、本发明的应用或用途。
通篇使用的范围用作描述范围内的每个值的简略表达方式。范围内的任何值可选为范围终点。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。
本发明的口腔护理组合物包含具有下式的烷基醚硫酸盐表面活性剂
[R(OC2H4)xOSO3]2M
其中
R为具有8-30个碳原子的烷基链长的饱和或不饱和烷基；
x为0至10；并且
M是选自锌阳离子、铜阳离子和亚锡阳离子的二价金属阳离子。
在某些实施方案中，本发明的口腔护理组合物包含各自具有下式的表面活性剂分子的混合物
[R(OC2H4)xOSO3]2M
其中
R为具有8-30个碳原子的烷基链长的饱和或不饱和烷基；
x为0至10；并且
M是选自锌阳离子、铜阳离子和亚锡阳离子的二价金属阳离子。
用于本发明组合物中的阴离子表面活性剂在头部和烃尾部包含阴离子硫酸盐基团。烷基醚硫酸盐(即其中x大于1的式[R(OC2H4)xOSO3]2M的化合物)通常制备为环氧乙烷与具有约8至约30个碳原子的一元醇的缩合产物。醇可以来源于脂肪如椰子油、棕榈油、牛脂，或者可以是合成醇。在某些实施方案中，用于本发明组合物中的表面活性剂(例如烷基醚硫酸盐)由衍生自椰子油和棕榈油的直链醇制备。在某些实施方案中，本发明的组合物包含由衍生自椰子油的直链醇制备的烷基醚硫酸盐。椰子油包含脂肪酸混合物，并且可以包含辛酸饱和C8脂肪酸、癸酸饱和C10脂肪酸、月桂酸饱和C12脂肪酸、肉豆蔻酸饱和C14脂肪酸、棕榈酸饱和C16脂肪酸和油酸单不饱和C18：1脂肪酸。醇可以与1摩尔至约10摩尔的环氧乙烷反应，所得产物被硫酸化并中和。通过这种方法获得的表面活性剂可以包含具有不同R基团(烷基链长)和不同乙氧基化程度(x)的组分的混合物。
本发明的口腔护理组合物可以包含单独的表面活性剂化合物的混合物，例如烷基醚硫酸盐化合物的混合物。在某些实施方案中，组合物包含化合物的混合物，其中混合物具有8-16个碳原子，例如12-16个碳原子的平均烷基链长(R)。烷基链R可以是饱和或不饱和的、直链或支链的。在某些实施方案中，组合物包含平均烷基链长为约12至约16个碳原子和平均乙氧基化程度为约1至约4摩尔环氧乙烷(即，x的平均值为1至4)的烷基醚硫酸盐化合物的混合物。在某些实施方案中，组合物包含表面活性剂，其中R是具有11个碳原子的直链非支化烷基链，并且x是3。在某些实施方案中，组合物可以包含化合物的混合物，所述混合物具有约0至约20重量％的烷基链长(R)为12至13个碳原子的化合物；约60至约100重量％的烷基链长(R)为14至16个碳原子的化合物；0至约20重量％的烷基链长(R)为17至19个碳原子的化合物；约45重量％至约90重量％的x为约1至约4的化合物；约10重量％至约25重量％的x为5至8的化合物以及约0.1重量％至约15重量％的x为9至10的化合物。
本发明的表面活性剂包含可以提供口腔护理益处的金属阳离子。已知某些金属离子提供治疗性口腔护理益处，包括抗菌活性、减少牙斑和/或减少口腔恶臭(口臭)。但是，将金属盐掺入口腔护理产品中会导致令人不悦的味涩感官感觉，诸如口腔中的干燥、起皱感。通过将有益的金属阳离子以烷基醚硫酸盐表面活性剂的形式掺入口腔护理组合物中，本发明人已经发现可以在较低水平的总金属下配制能够提供高水平的抗菌功效的组合物。因此，组合物中金属的令人不悦的涩味被最大程度减轻，而不损害所得的口腔护理益处。
在某些实施方案中，M是二价亚锡(锡)、铜或锌阳离子。在某些实施方案中，M是锌(II)阳离子。在某些实施方案中，本发明的组合物包含烷基醚硫酸锌表面活性剂。在某些实施方案中，本发明的口腔护理组合物包含烷基醚硫酸锌表面活性剂，例如基于椰子油的烷基醚硫酸锌表面活性剂。在某些实施方案中，本发明的组合物包含椰油醇硫酸酯锌。在某些实施方案中，本发明的组合物包含椰油醇聚醚硫酸酯锌。适用于本发明组合物的表面活性剂是由Zschimmer&Schartz以名称ZETESOL ZN出售的椰油醇聚醚硫酸酯锌。在某些实施方案中，椰油醇聚醚硫酸酯锌以25％溶液的形式掺入组合物中，即作为包含25％活性物质的溶液。
在某些实施方案中，烷基醚硫酸盐按组合物的总重量计以0.10重量％至10.0重量％活性物质的量存在于口腔护理组合物中。在某些实施方案中，烷基醚硫酸盐按组合物的总重量计以0.20重量％至8.0重量％活性物质，按组合物的总重量计以0.20重量％至6.0重量％活性物质，按组合物的总重量计以0.20重量％至5.0重量％活性物质，按组合物的总重量计以0.50重量％至10.0重量％活性物质，按组合物的总重量计以0.50重量％至8.0重量％活性物质，按组合物的总重量计以1.0重量％至8.0重量％活性物质或按组合物的总重量计以1.0重量％至5.0重量％活性物质的量存在于口腔护理组合物中。例如，在某些实施方案中，口腔护理组合物按组合物的总重量计可以包含0.10重量％至10.0重量％的椰油醇聚醚硫酸酯锌、0.20重量％至8.0重量％的椰油醇聚醚硫酸酯锌、0.20重量％至6.0重量％的椰油醇聚醚硫酸酯锌、0.20重量％至5.0重量％的椰油醇聚醚硫酸酯锌、0.50重量％至10.0重量％的椰油醇聚醚硫酸酯锌、0.50重量％至8.0重量％的椰油醇聚醚硫酸酯锌、1.0重量％至8.0重量％的椰油醇聚醚硫酸酯锌或1.0重量％至5.0重量％的椰油醇聚醚硫酸酯锌。
在某些实施方案中，组合物是洁齿剂、漱口水或漱口液。在某些实施方案中，组合物是牙膏、透明糊剂或凝胶。在某些实施方案中，组合物是待施用于嘴唇的糊剂或凝胶。在某些实施方案中，组合物是洁齿剂，诸如牙膏或凝胶。
在某些实施方案中，口腔护理组合物包含阳离子抗菌剂。在某些实施方案中，阳离子抗菌剂选自：苄索氯铵、奥替尼啶、海克替啶、己脒定、西吡氯铵(CPC)、阿来西定、Nα-酰基氨基酸烷基酯盐(诸如月桂酰基精氨酸乙酯盐酸盐(ELAH))及其混合物。
本发明的组合物可以包含氟离子源。在某些实施方案中，组合物包含一种或多种氟离子源，例如可溶性氟化物盐。适用于本发明的氟化物源可以包括但不限于：离子氟化物，包括碱金属氟化物；胺氟化物，诸如奥拉氟(N′-十八烷基三乙烯二胺-N，N，N′-三(2-乙醇)-二氢氟化物)、氟化铟、氟化钠、氟化钾、氟化钙、氟化锌、氟化铵锌、氟化锂、氟化铵、氟化亚锡、氟锆酸亚锡、单氟磷酸钠、单氟磷酸钾、月桂胺氢氟酸盐(laurylaminehydrofluoride)、二乙基氨基乙基辛酰基酰胺氢氟酸盐(diethylaminoethyloctoylamidehydrofluoride)、二癸基二甲基氟化按、十六烷基氟化吡啶鎓、二月桂基氟化吗啉鎓(dilaurylmorpholinium fluoride)、肌氨酸氟化亚锡(sarcosine stannous fluoride)、甘氨酸氟化钾(glycine potassium fluoride)、甘氨酸氢氟酸盐、氟化胺或其组合；以及离子单氟磷酸盐，包括碱金属单氟磷酸盐诸如氟化钾、氟化钠和氟化铵，以及单氟磷酸盐及其混合物。
在某些实施方案中，组合物包含选自以下一者或多者的氟离子源：氟化亚锡、氟化钠、氟化钾、单氟磷酸钠、氟硅酸钠、氟硅酸铵、氟化胺、氟化铵以及其两种或更多种的组合。
在某些实施方案中，组合物包含单氟磷酸钠。
在某些实施方案中，本发明的口腔护理组合物包含氟离子或提供氟的成分的来源，所述来源的量足以提供约50至约5000ppm的氟离子，例如，约100至约1000ppm、约200至约500ppm或约250ppm的氟离子。氟离子源可以按约0.001重量％至约10重量％，例如约0.003重量％％至约5重量％，0.01重量％至约1重量％，或约0.05重量％的水平加入本发明的组合物中。然而，应当理解，提供适当水平的氟离子的氟化物盐的重量将显然基于盐中的抗衡离子的重量而变化，并且本领域技术人员可以容易地确定这样的量。
在某些实施方案中，组合物包含足以提供约25ppm至约25,000ppm氟离子，例如约500ppm至约200ppm、约1000ppm至约1600ppm的量的氟离子源。
在某些实施方案中，组合物包含约0.03至约5.0重量％的单氟磷酸钠，例如约0.5至约2.0重量％、0.90至约1.30重量％、约0.90至约1.20重量％的单氟磷酸钠或约1.00至约1.20重量％的单氟磷酸钠。
所述组合物还可包含至少一种调味剂，所述调味剂可用于例如增强组合物的味道。可使用任何口腔可接受的天然或合成的调味剂，包括但不限于香草醛、鼠尾草、马郁兰、欧芹油、留兰香油、肉桂油、冬青油(水杨酸甲酯)、薄荷油、丁香油、月桂油、茴香油、桉树油、柑橘油、水果油和水果香精(包括源自柠檬、桔子、酸橙、葡萄柚、杏子、香蕉、葡萄、苹果、草莓、樱桃、菠萝等的那些)、源自豆类和坚果的调味剂(诸如咖啡、可可、可乐果、花生、杏仁)等，吸附的和包封的调味剂等。还涵盖在本文的调味剂之内的是在口中提供芳香和/或其他感官效果(包括凉爽或温热效果)的成分。此类成分例示性地包括薄荷醇、乙酸薄荷酯、乳酸薄荷酯、樟脑、桉树油、桉油醇、茴香脑、丁香酚、肉桂(cassia)、覆盆子酮(oxanone)、α-紫罗兰酮、丙烯基乙基愈创木酚(propenyl guaiethol)、麝香草酚、里哪醇、苯甲醛、肉桂醛、N-乙基-对-薄荷烷-3-甲酰胺(N-ethyl-p-menthan-3-carboxamine)、N，2，3-三甲基-2-异丙基丁酰胺、3-(1-薄荷氧基)-丙烷-1，2-二醇、肉桂醛甘油缩醛(CGA)、薄荷酮甘油缩醛(MGA)等。按组合物的总重量计，一种或多种调味剂任选的存在总量为约0.01重量％％至约5重量％，例如约0.1重量至约2.5重量％。
本发明的组合物任选地包含一种或多种抗敏剂，例如钾盐如硝酸钾、碳酸氢钾、氯化钾、柠檬酸钾和草酸钾；辣椒素；丁香酚；锶盐；及其组合。此类试剂可以按组合物的总重量计以例如约1重量％％至约20重量％的有效量添加，具体取决于所选的试剂。
在某些实施方案中，组合物可以包含一种或多种螯合剂。在某些实施方案中，组合物包含一种或多种能够络合细菌细胞壁中发现的钙的螯合剂。在某些实施方案中，组合物包含一种或多种可溶性焦磷酸盐作为螯合剂。在某些实施方案中，焦磷酸盐可以是任何碱金属焦磷酸盐。在某些实施方案中，盐包括四碱金属焦磷酸盐、二碱金属焦磷酸二氢盐、三碱金属焦磷酸一氢盐及其混合物，其中碱金属为钠或钾。在某些实施方案中，组合物包含这样的焦磷酸盐，其量将提供至少约1重量％的焦磷酸盐离子，例如约1.5重量％至约6重量％或约3.5重量％至约6重量％。
在某些实施方案中，本发明的组合物包含一种或多种聚合物，诸如聚乙二醇、聚乙烯基甲醚-马来酸共聚物和多糖(例如，纤维素衍生物诸如羧甲基纤维素或微晶纤维素，或多糖胶诸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。
在某些实施方案中，组合物包含约0.05至约5％的增强口腔护理剂递送及其在口腔表面上的保留的试剂。在某些实施方案中，组合物包含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，优选具有约30,000至约1,000,000的分子量的甲基乙烯基醚/马来酸酐。在某些实施方案中，组合物包含约0.05至约3重量％的此类试剂。
在某些实施方案中，组合物包含增稠材料以增强制剂的性能。在某些实施方案中，增稠剂是二氧化硅、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、***树胶和黄芪胶包含在内。在某些实施方案中，组合物包含胶体硅酸铝镁或细分的二氧化硅。在某些实施方案中，增稠剂以约0.5至约5.0％的量存在。在某些实施方案中，组合物包含约0.5至约5％的纤维素胶。在某些实施方案中，组合物包含1.0-10重量％的无定形二氧化硅。
在某些实施方案中，组合物包含一种或多种湿润剂。湿润剂可防止组合物在暴露于空气时硬化。在某些实施方案中，组合物包含一种或多种选自可食用多元醇如甘油、山梨糖醇、木糖醇、丙二醇及其混合物的湿润剂。在某些实施方案中，组合物包含约5至约25％的湿润剂。在某些实施方案中，组合物包含约5至约25％的甘油。
在某些实施方案中，组合物包含一种或多种研磨剂。在某些实施方案中，组合物包含硅胶或沉淀二氧化硅磨料。在某些实施方案中，组合物包含5至30重量％的二氧化硅磨料。
口腔护理组合物可包含至少一种甜味剂，所述甜味剂可用于例如增强组合物的味道。一种或多种甜味剂任选的存在总量密切取决于选择的特定甜味剂，但是通常为按组合物的总重量计0.005重量％至5重量％，任选地0.01重量％至1重量％，还任选地按口腔护理组合物的总重量计0.1重量％至0.5重量％。
口腔护理组合物可包含至少一种着色剂。本文中的着色剂包括颜料、染料、色淀和赋予特定光泽或反射率的试剂诸如珠光剂。可使用任何口服可接受的着色剂。本文中的着色剂包括颜料、染料、色淀和赋予特定光泽或反射率的试剂诸如珠光剂。在某些实施方案中，使用白色着色剂，例如二氧化钛(TiO2)、二氧化钛色覆云母(例如Timiron)、矿物质或粘土。按口腔护理组合物的总重量计，一种或多种着色剂任选的存在总量为约0.0001重量％至约5重量％，例如约0.0001重量％至约1重量％，或约0.0005重量％至约0.1重量％。
组合物还可以包含抗氧化剂。可以使用任何口腔可接受的抗氧化剂，包括丁基化羟基茴香醚(BHA)、丁基化羟基甲苯(BHT)、维生素A、类胡萝卜素、维生素E、黄酮类、多酚类、抗坏血酸、草药抗氧化剂、叶绿素、褪黑素及其混合物。
本发明的组合物可以另外任选地包含牙垢控制剂(抗牙结石剂)。可用于本文的牙垢控制剂包括特定试剂的盐，包括碱金属盐和铵盐。所述试剂包括：磷酸盐和多磷酸盐(例如，焦磷酸盐)、聚氨基丙烷磺酸(AMPS)、聚烯烃磺酸盐、聚烯烃磷酸盐、二磷酸盐诸如氮杂环烷烃-2，2-二磷酸盐(例如，氮杂环庚烷-2，2-二磷酸)、N-甲基氮杂环戊烷-2，3-二磷酸、乙烷-1-羟基-1，1-二磷酸(EHDP)以及乙烷-1-氨基-1，1-二磷酸盐、磷酰基烷烃羧酸。可用的无机磷酸盐和多磷酸盐包括磷酸氢二钠、磷酸二氢钠和磷酸钠、三聚磷酸钠、四聚磷酸钠、焦磷酸单钠、焦磷酸二钠、焦磷酸三钠和焦磷酸四钠、三偏磷酸钠、六偏磷酸钠及其混合物。其他可用的牙垢控制剂包括聚羧酸盐聚合物、羧酸盐-磷酸盐共聚物和聚乙烯基甲基醚/马来酸酐(PVME/MA)共聚物，诸如在某些实施方案中，本发明的组合物包含0.1至45重量％的牙垢控制剂。在某些实施方案中，本发明的组合物可以包含0.1至45重量％的多磷酸盐，例如20至30重量％的多磷酸盐。
在一些实施方案中，本发明的组合物还包含营养剂。合适的营养素包括维生素、矿物质、氨基酸及其混合物。维生素包括维生素C和D、硫胺、核黄素、泛酸钙、烟酸、叶酸、烟酰胺、吡哆醇、氰钴胺、对氨基苯甲酸、生物类黄酮及其混合物。营养补充剂包括氨基酸(例如L-色氨酸、L-赖氨酸、甲硫氨酸、苏氨酸、左卡尼汀和L-肉毒碱)、亲脂物质(诸如胆碱、肌醇、甜菜碱和亚油酸)及其混合物。
可在口腔可接受的载体或媒介物中提供口腔组合物。载体可以是液体、半固体或固相的，呈漱口液、洁齿剂(包括牙膏、牙粉和预防用牙膏)、糖果(包括锭剂和口香糖)、药物、薄膜的形式或本领域技术人员已知的任何其他形式。对特定载体组分的选择取决于所需的产品形式。
可以用于形成上面列出的载体的常规成分是技术人员已知的。如本领域的技术人员所认识到，口腔组合物除了之前所述的那些组分外还任选地包含其他材料，包括例如表面活性剂、乳化剂和泡沫调节剂、粘度改性剂和增稠剂、湿润剂、稀释剂、另外的pH调节剂、润肤剂、保湿剂、口感剂、甜味剂、调味剂、着色剂、防腐剂、溶剂(诸如水)及其组合。任何给定的一种材料均可起到在材料的这些类别的两种或更多种中的目的。优选地，针对与活性成分的所有组分(包括蜂胶提取物)和为口腔组合物选择的一种或多种口腔护理活性化合物的相容性和稳定性来选择此类载体材料。
典型的可用的表面活性剂在上文提及和讨论的专利参考文献中公开，包括在美国专利号4,894,220中公开。表面活性剂通常是口腔组合物的重要方面，因为它们可以起到表面活性剂、乳化剂泡沫调节剂和/或活性成分分散剂的作用。因此，针对与活性成分组分的相容性对它们进行选择是重要的。例如，在口腔组合物具有包含阳离子抗菌剂的活性成分的实施方案中，优选的是，载体包含不是强阴离子的表面活性剂，因为此类阴离子化合物可以与阳离子活性成分结合，从而可能降低其生物利用率。
合适的表面活性剂是在宽pH范围内合理地稳定并起泡的那些试剂。这些化合物是本领域已知的，并包括非皂阴离子(例如，月桂基硫酸钠(SLS)、N-肉豆蔻酰和N-棕榈酰肌氨酸)、非离子(例如，聚山梨醇酯20(聚氧乙烯(20)失水山梨醇单月桂酸酯，TWEEN.RTM.20)和聚山梨醇酯80(聚氧乙烯(20)失水山梨醇单月桂酸酯，TWEEN.RTM.80)、可以商品名Pluronic.RTM.F127得自BASF Corporation的泊洛沙姆407)、阳离子、两性离子(例如，椰油酰胺丙基甜菜碱和月桂酰胺丙基甜菜碱)和两性有机合成洗涤剂。在活性成分包含阳离子化合物的实施方案中，表面活性剂可选自：非离子表面活性剂、阳离子表面活性剂、甜菜碱表面活性剂、两性表面活性剂或其混合物。在多种实施方案中，一种或多种表面活性剂以约0.001％至约5％或约0.5％至约2.5％的量存在于口腔组合物中。
在口腔组合物呈漱口液或漱口水形式的实施方案中，示例性载体基本上为液体。术语“漱口液”包括漱口水、喷雾、漱口剂等。在这样的制备物中，口腔可接受的载体通常具有包含水或水与醇的混合物的水相。另外，在多种实施方案中，口腔载体通常具有湿润剂、表面活性剂和pH缓冲剂。
本发明的组合物可用于治疗牙龈炎和/或牙周炎。牙龈炎和牙周炎是口腔的牙周组织的炎症状态。牙龈炎(牙龈组织或齿龈的炎症)可以通过治疗和良好的口腔卫生来逆转，但是如果不经治疗则可能会发展为牙周炎(牙周组织的炎症)。未经治疗的牙周炎最终会导致牙齿脱落。本发明的组合物可通过任何方式施用于受试者的口腔(特别是人或动物受试者的口腔)。施用手段可以根据口腔护理组合物的制剂而变化。例如，在某些实施方案中，口腔护理组合物是洁齿剂，并且可以使用器具(例如刷子、牙刷、棒、海绵或棉签)局部施用于口腔。在某些实施方案中，口腔护理组合物为漱口水或漱口液的形式，并通过灌洗(“漱口”)施用于口腔。在某些实施方案中，使用牙托盘将口腔护理组合物施用于口腔中的表面。在某些实施方案中，使用牙条(dental strip)将口腔护理组合物施用于口腔中的表面，例如通过将包含口腔护理组合物的条粘附至牙齿或牙龈的表面。在某些实施方案中，使用口腔护理笔将口腔护理组合物施用至口腔。在某些实施方案中，口腔护理组合物每天至少一次或至少两次施用于口腔。
本发明的组合物可包含本文的一个实例中描述的第一特征以及本文另一个实例中描述的第二特征。换句话讲，本发明考虑以各种组合来混合并搭配来自所公开的实施方案的特征。
实施例
实施例1
使用细胞活力测定法将0.5重量％的相当于0.0393重量％元素锌的椰油醇聚醚硫酸酯锌溶液(得自Zschimmer&Schwarz的ZETESOL ZN，作为具有23.5-25.5％活性ZCS的组合物提供)的抗菌功效与0.5重量％的月桂基醚硫酸钠(月桂醇醚硫酸钠或SLES)以及1.0重量％氧化锌和0.5重量％柠檬酸锌(相当于0.8重量％元素锌)的含水混合物的抗菌功效进行了比较。在基于代谢活性细菌减少蓝色染料刃天青能力的测定中测试这些化合物。使用代表性口腔细菌物种的五个物种的组合来模拟口腔环境的复杂细菌菌群。将包含粘性放线菌(Actinomyces viscosus)、干酪乳杆菌(Lactobacillus casei)、口腔链球菌(Streptococcus oralis)、核粒梭菌(Fusobacteriaum nucleatum)和小韦荣氏菌(Veillonella parvulal)的细菌混合物与所研究的化合物一起在37℃下温育1小时，中和，洗涤并用50μg/ml刃天青溶液染色。当用刃天青温育活的细菌时，蓝色非荧光染料被细菌还原成粉色荧光试卤灵(resrufin)。在560nm激发/590nm发射下读取测试样品的荧光并将其与活细菌和死细菌的标准混合物的荧光相比较，以确定在温育之后活着的初始群体的百分比。表1中提供了该测定的结果：
表1
该测定的结果表明，椰油醇聚醚硫酸酯锌(ZCS)比单独的表面活性剂或0.8重量％全元素锌的水溶液明显更有效。
实施例2
制备包含椰油醇聚醚硫酸酯锌的洁齿剂组合物，并使用如实施例1中所述的刃天青细胞活力测定法研究这些配方的体外抗菌功效。表2中提供了这些组合物的制剂。
表2
为了使配方赋形剂的影响最小化，在该测定中使用稀释的1∶100和1∶100的洁齿剂制剂在水中的浆液。如前所述，将测试化合物(作为稀浆液)与细菌一起在37℃下温育1小时，中和，洗涤并用50μg/ml刃天青溶液染色。然后确定活细菌的百分比。结果在表3中示出。
表3
证实ZCS组合物的益处的进一步数据如图1所示，其中0.4％ZCS相当于0.98％ZnCit，而1％ZCS相似于1.24％ZnCit，且2％ZCS相当于1％ZCS+1.12％ZnCit。该图表表明，在有或没有ZnCit的情况下，ZCS的进一步增加似乎表现出同样有效。含有1.5％SLS的2和3％ZCS似乎比其他SLS组合物更好。在10％的处理稀释度下，细菌活力严重降低，使得不能区分测试样品。然而，用10％的0.4和1％ZCS溶液处理似乎表现比ZnCit样品好。以相对低水平的总锌包含ZCS的配方使得当从传统的锌化合物诸如柠檬酸锌递送时产生与0.8％元素锌相当的功效。ZCS递送的锌可以提供具有高水平的体外抗菌功效的配方。因此，可以提供抗菌功效，同时避免现有锌制剂的负面味道影响。
实施例3
如表4所示制备含有椰油醇聚醚硫酸酯锌的漱口水组合物。
| 成分(重量％) | 漱口水A |
| DM水、甜味剂、调味剂、着色剂 | 79.17 |
| 泊洛沙姆407 | 0.40 |
| CPC | 0.075 |
| 氟化钠 | 0.05 |
| 椰油醇聚醚硫酸酯锌，25％溶液 | 0.20 |
| 山梨酸钾 | 0.05 |
| 湿润剂 | 20.00 |
| 乳酸 | 0.053 |
表4。
Claims (26)
1.一种包含具有下式的表面活性剂的口腔护理组合物
[R(OC2H4)xOSO3]2M
其中
R为具有8-30个碳原子的烷基链长的饱和或不饱和烷基；
x为0至10；并且
M是选自锌阳离子、铜阳离子和亚锡阳离子的二价金属阳离子。
2.根据权利要求1所述的口腔护理组合物，其中所述表面活性剂按所述组合物的总重量计以0.10重量％至10.0重量％的量存在。
3.根据任一项前述权利要求所述的口腔护理组合物，其中R是具有10至18个碳原子的饱和或不饱和烷基。
4.根据任一项前述权利要求所述的口腔护理组合物，其中R是具有10至18个碳原子的饱和烷基。
5.根据任一项前述权利要求所述的口腔护理组合物，其中x为1至4。
6.权利任一项前述权利要求所述的口腔护理组合物，其中R是具有11个碳原子的饱和烷基，并且其中x是3。
7.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物包含下式的表面活性剂化合物的混合物
[R(OC2H4)xOSO3]2M，
所述表面活性剂化合物具有10至16个碳原子的平均烷基链长。
8.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物包含具有1至4的x平均值的表面活性剂化合物的混合物。
9.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物包含表面活性剂化合物的混合物，所述表面活性剂化合物具有10至16个碳原子的平均烷基链长和1至4的x平均值。
10.根据任一项前述权利要求所述的口腔护理组合物，其中M为Zn(II)阳离子。
11.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物按所述组合物的总重量计包含0.01重量％至1.0重量％的M。
12.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物按所述组合物的总重量计包含0.01重量％至0.80重量％的M、0.01重量％至0.75重量％的M、0.01重量％至0.60重量％的M、0.01重量％至0.50重量％的M或0.02重量％至0.20重量％的M。
13.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物包含椰油醇硫酸酯锌或椰油醇聚醚硫酸酯锌。
14.根据任一项前述权利要求所述的口腔护理组合物，其中所述口腔护理组合物包含椰油醇聚醚硫酸酯锌。
15.根据任一项前述权利要求所述的口腔护理组合物，其还包含口腔可接受的媒介物。
16.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物为洁齿剂或漱口水。
17.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物还包含氟离子源。
18.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物还包含选自柠檬酸锌、硫酸锌、氧化锌、氟化锌、氯化锌、乳酸锌、葡萄糖酸锌、苹果酸锌、酒石酸锌、碳酸锌、磷酸锌及其混合物的锌离子源。
19.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物还包含不含锌的阴离子表面活性剂。
20.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物还包含月桂基硫酸钠。
21.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物还包含二氧化硅。
22.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物还包含多磷酸盐。
23.根据任一项前述权利要求所述的口腔护理组合物，其中所述组合物为洁齿剂，其包含：
0.10重量％至10.0重量％的椰油醇聚醚硫酸酯锌；和
0.05重量％至5.0重量％的月桂基硫酸钠。
24.一种用于以下项的方法：
(i)治疗牙龈炎和/或牙周炎，
(ii)减少牙斑积聚和/或
(iii)减少受试者口腔中的细菌
所述方法包括将根据任一项前述权利要求所述的组合物施用于受试者的口腔。
25.一种在用于以下项的方法中使用的根据权利要求1至23中任一项所述的组合物：
(i)治疗牙龈炎和/或牙周炎，
(i)减少牙斑积聚和/或
(ii)减少受试者口腔中的细菌，
所述方法包括将组合物施用于受试者的口腔。
26.根据权利要求1至23中任一项所述的组合物在用于以下方面中的用途：
(i)治疗牙龈炎和/或牙周炎，
(ii)减少牙斑积聚和/或
(iii)减少受试者口腔中的细菌。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2015/040927 WO2017014723A1 (en) | 2015-07-17 | 2015-07-17 | Oral care compositions |
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| Publication Number | Publication Date |
|---|---|
| CN107847405A true CN107847405A (zh) | 2018-03-27 |
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| CN201580081667.1A Pending CN107847405A (zh) | 2015-07-17 | 2015-07-17 | 口腔护理组合物 |
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| Country | Link |
|---|---|
| US (1) | US10736831B2 (zh) |
| EP (1) | EP3316852A1 (zh) |
| CN (1) | CN107847405A (zh) |
| AU (1) | AU2015402571B2 (zh) |
| BR (1) | BR112018000826A2 (zh) |
| CA (1) | CA2991917A1 (zh) |
| IL (1) | IL256719B (zh) |
| MX (1) | MX2018000635A (zh) |
| RU (1) | RU2726198C2 (zh) |
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| ZA (1) | ZA201800096B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115463043A (zh) * | 2022-08-25 | 2022-12-13 | 克劳丽化妆品股份有限公司 | 一种口腔护理组合物及漱口水 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021059215A2 (en) | 2019-09-25 | 2021-04-01 | Church & Dwight Co., Inc. | Oral care composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1074247A2 (en) * | 1999-07-20 | 2001-02-07 | Zschimmer & Schwarz Italiana S.p.A. | Cleansing or cosmetic compositions comprising zinc alkylsulphates and/or alky(poly)ethoxysulphates as surfactants and preservatives |
| EP2399576A1 (en) * | 2010-06-25 | 2011-12-28 | Farmaceutici Dott. Ciccarelli S.p.A. | Use of antibacterial compounds for the oral cavity hygiene |
| WO2014100930A1 (en) * | 2012-12-24 | 2014-07-03 | Colgate-Palmolive Company | Oral care composition |
| DE102014223535A1 (de) * | 2014-11-18 | 2015-07-23 | Henkel Ag & Co. Kgaa | Mund- und Zahnpflege- und -reinigungsmittel mit verbesserter Plaqueentfernung |
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| JPS5236106A (en) | 1975-09-16 | 1977-03-19 | Kao Corp | Liquid detergent composition |
| US4894220A (en) | 1987-01-30 | 1990-01-16 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition |
| US5635466A (en) | 1992-08-21 | 1997-06-03 | The Procter & Gamble Company | Concentrated liquid detergent composition comprising an alkyl ether sulphate and a process for making the composition |
| US5980877A (en) | 1996-10-25 | 1999-11-09 | The Procter & Gamble Company | Conditioning shampoo composition |
| AR031782A1 (es) | 2000-12-05 | 2003-10-01 | Colgate Palmolive Co | Dentifrico de astringencia reducida, que contiene zinc |
| EP1698324A1 (en) * | 2004-11-09 | 2006-09-06 | The Procter & Gamble Company | Zinc-containing dentifrice compositions having an improved taste |
| DK2101720T3 (en) | 2006-12-13 | 2016-06-13 | Aseptix Res Bv | Mild composition for skin disinfection |
| FR2980691B1 (fr) | 2011-09-30 | 2014-03-14 | Galderma Sa | Composition de lavage |
| FR2992859B1 (fr) | 2012-07-09 | 2014-10-03 | Fabre Pierre Dermo Cosmetique | Utilisation de coceth sulfate de zinc comme agent antibacterien vis a vis de propionibacterium acnes |
-
2015
- 2015-07-17 CA CA2991917A patent/CA2991917A1/en not_active Abandoned
- 2015-07-17 RU RU2018101668A patent/RU2726198C2/ru active
- 2015-07-17 BR BR112018000826A patent/BR112018000826A2/pt active Search and Examination
- 2015-07-17 CN CN201580081667.1A patent/CN107847405A/zh active Pending
- 2015-07-17 WO PCT/US2015/040927 patent/WO2017014723A1/en active Application Filing
- 2015-07-17 MX MX2018000635A patent/MX2018000635A/es unknown
- 2015-07-17 US US15/745,484 patent/US10736831B2/en active Active
- 2015-07-17 AU AU2015402571A patent/AU2015402571B2/en not_active Ceased
- 2015-07-17 EP EP15745667.4A patent/EP3316852A1/en active Pending
-
2018
- 2018-01-03 IL IL256719A patent/IL256719B/en active IP Right Grant
- 2018-01-05 ZA ZA2018/00096A patent/ZA201800096B/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1074247A2 (en) * | 1999-07-20 | 2001-02-07 | Zschimmer & Schwarz Italiana S.p.A. | Cleansing or cosmetic compositions comprising zinc alkylsulphates and/or alky(poly)ethoxysulphates as surfactants and preservatives |
| EP2399576A1 (en) * | 2010-06-25 | 2011-12-28 | Farmaceutici Dott. Ciccarelli S.p.A. | Use of antibacterial compounds for the oral cavity hygiene |
| WO2014100930A1 (en) * | 2012-12-24 | 2014-07-03 | Colgate-Palmolive Company | Oral care composition |
| DE102014223535A1 (de) * | 2014-11-18 | 2015-07-23 | Henkel Ag & Co. Kgaa | Mund- und Zahnpflege- und -reinigungsmittel mit verbesserter Plaqueentfernung |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115463043A (zh) * | 2022-08-25 | 2022-12-13 | 克劳丽化妆品股份有限公司 | 一种口腔护理组合物及漱口水 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2018000635A (es) | 2018-04-24 |
| RU2726198C2 (ru) | 2020-07-09 |
| ZA201800096B (en) | 2019-09-25 |
| US20180207076A1 (en) | 2018-07-26 |
| WO2017014723A1 (en) | 2017-01-26 |
| EP3316852A1 (en) | 2018-05-09 |
| CA2991917A1 (en) | 2017-01-26 |
| AU2015402571A1 (en) | 2018-01-25 |
| RU2018101668A3 (zh) | 2019-08-19 |
| AU2015402571B2 (en) | 2018-12-20 |
| IL256719A (en) | 2018-03-29 |
| US10736831B2 (en) | 2020-08-11 |
| RU2018101668A (ru) | 2019-08-19 |
| IL256719B (en) | 2020-02-27 |
| BR112018000826A2 (pt) | 2018-09-04 |
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