CN107468587B - An oral care composition comprising stabilized polyphenols - Google Patents

An oral care composition comprising stabilized polyphenols Download PDF

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CN107468587B
CN107468587B CN201710825673.4A CN201710825673A CN107468587B CN 107468587 B CN107468587 B CN 107468587B CN 201710825673 A CN201710825673 A CN 201710825673A CN 107468587 B CN107468587 B CN 107468587B
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stannous
oral care
care composition
salts
acid
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CN107468587A (en
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华淑贞
周康
陈晓斌
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Hawley & Hazel Bvi Co ltd
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    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Abstract

The present invention discloses an oral care composition comprising a stabilized polyphenol comprising at least a polyphenol compound and a stannous ion source, the composition having a pH of from 5 to 8. The oral care composition and the product comprising the composition can ensure that the stability exists, and the residual quantity of the EGCg in the tea polyphenol can reach 86 percent after the composition is placed in an environment at 25 ℃ for one month.

Description

An oral care composition comprising stabilized polyphenols
Technical Field
The present invention relates to the field of oral care technology, in particular to an oral care composition comprising stable polyphenols.
Background
Plant extracts containing polyphenol are widely applied to oral care products such as toothpaste and the like, such as tea extracts, and a plurality of toothpaste products containing tea extracts are already available in the market and are popular with consumers. However, the molecular structure of the polyphenol compound contains a plurality of phenolic hydroxyl groups, and the polyphenol compound is easily oxidized to form complex quinones, so that the original antioxidant performance of the polyphenol is lost, and the oral composition is discolored. There is a need to improve stability in oral care products.
Disclosure of Invention
The technical problem to be solved by the present application is to provide an oral care composition comprising stable polyphenols. The composition can ensure the existence of stability, and after the composition is placed in an environment at 25 ℃ for one month, the residual quantity of the EGCg in the tea polyphenol can reach 86%.
In order to solve the technical problems, the invention adopts the following technical scheme:
an oral care composition comprising a stable polyphenol comprising at least a polyphenol compound and a stannous ion source, the composition having a pH of from 5 to 8.
According to certain preferred embodiments of the present application, the pH of the composition is from 5 to 7.5;
according to certain preferred embodiments of the present application, the composition has a pH of 5 to 7;
according to certain preferred embodiments of the present application, the composition has a pH of 6 to 7.
According to certain embodiments of the present application, the composition further comprises a pH adjusting agent to ensure that the pH of the composition is in the range of 5 to 8.
According to certain preferred embodiments of the present application, the pH adjusting agent includes, but is not limited to, sodium hydroxide, hydrochloric acid, sulfuric acid, citric acid and salts thereof, lactic acid and salts thereof, phosphoric acid and salts thereof, phthalic acid and salts thereof, pyrophosphoric acid and salts thereof, tripolyphosphoric acid and salts thereof, polyphosphoric acid and salts thereof, citric acid and salts thereof, acetic acid and salts thereof.
According to certain embodiments of the present application, the polyphenolic compound comprises one or more of the following compounds: epigallocatechin gallate (EGCg), Epicatechin gallate (ECG), Catechin (cathechin), Epicatechin (EC), and Epigallocatechin (EGC), and chlorogenic acid;
according to certain embodiments of the present application, the polyphenol derivative compound is a tea polyphenol
According to certain embodiments of the present application, the mass ratio of the stannous ion source to the polyphenolic compound is greater than 5: 1.
according to certain preferred embodiments of the present application, the mass ratio of the stannous ion source to the polyphenolic compound is greater than 10: 1.
according to certain most preferred embodiments of the present application, the mass ratio of the stannous ion source to the polyphenolic compound is greater than 100: 1.
according to certain embodiments of the present application, the polyphenolic compound is added to the oral care composition in an amount of from 0.0001 to 0.2 wt%.
According to certain embodiments of the present application, the stannous ion source is added in an amount of 0.001 to 1 wt% of the oral care composition.
According to certain embodiments of the present application, adjuvants such as abrasives, humectants and/or thickeners may further be included in the oral care composition;
according to certain embodiments of the present application, active ingredients such as antibacterial agents, anticaries agents, anti-sensitivity agents, anticalculus agents, and/or whitening agents may further be included in the oral care compositions;
any range recited herein is intended to include the endpoints and any number between the endpoints and any subrange subsumed therein or defined therein.
The starting materials of the present invention are commercially available, unless otherwise specified, and the equipment used in the present invention may be any equipment conventionally used in the art or may be any equipment known in the art.
Compared with the prior art, the invention has the following beneficial effects:
after being placed in an environment at 25 ℃ for one month, the residual amount of the EGCg in the tea polyphenol can reach 86%.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The present invention relates to an oral care composition comprising a stabilized polyphenol comprising at least a polyphenol compound and a stannous ion source, said composition having a pH of from 5 to 8.
Applicants have surprisingly found that maintaining the pH of a composition comprising a polyphenol and a stannous ion source between 5 and 8 substantially improves the stability of the composition.
According to certain preferred embodiments of the present application, the composition has a pH of 5 to 7.5, and the composition is more excellent in stability.
According to certain preferred embodiments of the present application, the composition has a pH of 5 to 7; the stability of the composition is particularly superior.
According to certain preferred embodiments of the present application, the composition has a pH of 6 to 7. The stability of the composition is most excellent.
According to certain preferred embodiments of the present application, a pH adjusting agent may be included in the composition to adjust the pH of the composition to between 5 and 8.
According to certain preferred embodiments of the present application, the pH adjusting agent includes, but is not limited to, one or more of sodium hydroxide, hydrochloric acid, sulfuric acid, citric acid and salts thereof, lactic acid and salts thereof, phosphoric acid and salts thereof, phthalic acid and salts thereof, pyrophosphoric acid and salts thereof, tripolyphosphoric acid and salts thereof, polyphosphoric acid and salts thereof, citric acid and salts thereof, acetic acid and salts thereof.
According to certain embodiments of the present application, the polyphenolic compound comprises one or more of the following compounds: epigallocatechin gallate (EGCg), Epicatechin gallate (ECG), Catechin (cathechin), Epicatechin (EC), and Epigallocatechin (EGC), and chlorogenic acid;
according to certain embodiments of the present application, the polyphenol derivative compound is a tea polyphenol
According to certain embodiments of the present application, the mass ratio of the stannous ion source to the polyphenolic compound is greater than 5: 1, or is greater than 10: 1, or is greater than 15: 1, or is greater than 20: 1, or is greater than 25: 1, or is greater than 30: 1, or is greater than 35: 1, or is greater than 40: 1, or is greater than 45: 1, or is greater than 50: 1, or is greater than 55: 1, or is greater than 60: 1, or is greater than 65: 1, or is greater than 70: 1, or is greater than 75: 1, or is greater than 80: 1, or is greater than 85: 1, or is greater than 90: 1, or is greater than 100: 1. but not more than 1000: 1.
according to certain embodiments of the present application, the polyphenolic compound is added to the oral care composition in an amount of from 0.0001 to 0.2 wt%.
According to certain embodiments of the present application, the stannous ion source is added in an amount of 0.001 to 1 wt% of the oral care composition.
According to certain embodiments of the present application, adjuvants such as abrasives, humectants and/or thickeners may further be included in the oral care composition;
the abrasive is the main raw material of the toothpaste, generally accounts for 20-50% of the formula, and has the most important functions of removing tartar and relieving dental calculus in the toothpaste. The abrasive material is selected with due regard to its hardness, size, shape and amount to ensure effective cleaning without abrading the teeth. Exemplary abrasives may include, but are not limited to, one or more of the following: calcium carbonate, calcium hydrogen phosphate, calcium pyrophosphate, tricalcium phosphate, aluminum silicate, aluminum hydroxide, alumina, zeolite, titanium oxide, silicic acid, kaolin, and the like.
"humectants" are ingredients that prevent the oral care composition from becoming dehydrated and hardened. Exemplary humectants include, but are not limited to, such as glycerin, propylene glycol, sorbitol, low molecular weight polyethylene glycols, and the like. The humectant is typically present in the oral care composition in an amount of 10 to 80% by mass.
The thickening agent is a rheological additive, can thicken the coating, prevent sagging phenomenon in construction, and endow the coating with excellent mechanical property and storage stability. There are many thickener types disclosed in the prior art, including inorganic thickeners, cellulosics, polyacrylates and associative polyurethane thickeners. Cellulosic thickeners include, but are not limited to, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methyl cellulose, and the like. Polyacrylate thickeners are classified into two categories: one is a water soluble polyacrylate; the other is a homopolymer or copolymer emulsion thickener of acrylic acid and methacrylic acid, which is acidic in nature and needs to be neutralized to pH 8-9 with alkali or ammonia water to achieve thickening effect, and is also called an acrylic acid-base swelling thickener. Polyurethane thickeners are newly developed associative thickeners in recent years. Inorganic thickeners are a class of gel minerals that swell on absorbing water to form thixotropy. Exemplary inorganic thickeners include, but are not limited to, bentonite, attapulgite, aluminum silicate, and the like.
According to certain embodiments of the present application, active ingredients such as antibacterial agents, anticaries agents, anti-sensitivity agents, anticalculus agents, and/or whitening agents may further be included in the oral care compositions;
by "antibacterial agent" is meant a chemical substance that is capable of maintaining the growth or reproduction of certain microorganisms in an oral care composition below a necessary level over a period of time. Exemplary antimicrobial agents include, but are not limited to: zinc oxide, stannous chloride, tetrahydrocurcumin, cetylpyridinium chloride, triclosan and the like.
"anticaries agent" means a substance having an inhibitory effect on caries, for example, a substance which enhances the anticaries ability of teeth by decreasing the solubility of enamel hydroxyapatite, or a substance which controls plaque, inhibiting bacterial growth. Exemplary anticaries agents include, but are not limited to, a fluoride ion source (e.g., sodium fluoride, potassium fluoride, calcium fluoride, magnesium fluoride, stannous fluoride, ammonium fluoride, sodium monofluorophosphate, potassium monofluorophosphate, fluorosilicate salts, etc.), a phosphorous-containing agent (calcium phosphate, sodium trimetaphosphate, magnesium glycerophosphate, calcium lactate, sodium caseinate, etc.), or arginine and its derivatives. Preferably, in certain embodiments, the anticaries agent comprises a fluoride ion source.
An "anti-sensitivity agent" refers to a substance that prevents or treats dentinal hypersensitivity by inhibiting nerve impulses or being capable of closing or decreasing the permeability of dentinal tubules. Exemplary anti-sensitivity agents include, but are not limited to: potassium ion sources such as dipotassium glycyrrhizinate, potassium fluoride, potassium nitrate, potassium chloride and the like. Preferably, in certain embodiments, the anti-sensitivity agent comprises a source of potassium ions.
"anticalculus agent" refers to a metal ion complex that acts to combat dental calculus. Exemplary anticalculus agents include, but are not limited to: pyrophosphate, tripolyphosphate, hexametaphosphate or citrate.
The "whitening agent" refers to a substance having a whitening effect on teeth. Exemplary whitening agents include, but are not limited to: peroxide bleaching agent, papain and glucose oxidase.
The stability test method of the oral care composition of the present invention is based on: tea polyphenols are mixtures comprising a variety of different polyphenolic compounds, such as epigallocatechin gallate (EGCg), Epicatechin gallate (ECG), Catechin (cathhin), Epicatechin (EC), and Epigallocatechin (EGC). The content of tea polyphenols may be indirectly characterized by the content of EGCg. EGCg is a major bioactive monomer in tea polyphenols. EGCg is determined by methods well known in the art. For example, by HPLC-MS-MS or LC-MS.
Example 1-example 8: oral care compositions
1mol/L sodium hydroxide solution and 1mol/L pyrophosphoric acid solution are prepared, and the two solutions are mixed to prepare buffer solutions with pH2.0, pH4.0, pH5.0, pH6.0, pH7.0, pH7.5, pH8.0 and pH10.0.
The raw materials and amounts of the compositions of examples 1-8 are shown in Table 1 below:
TABLE 1
Figure BDA0001407464320000051
Wherein the content of EGCg in the tea polyphenol material is 64.2%.
The stability test results for examples 1-8 are shown in Table 2 below:
the compositions of the above formulation examples 1 to 8 were placed in an environment of 25 c, 40 c and 50 c, respectively, and tested for the content of EGCg therein by HPLC method when left for one month (aging) to evaluate the stability of tea polyphenol. The test results are shown in table 2.
TABLE 2 EGCg assay results after 1 month aging of the compositions of examples 1-8 (%)
Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8
25℃ 0.0471 0.0553 0.0613 0.0632 0.0629 0.0638 0.0536 0.0559
40℃ 0.0329 0.0415 0.0597 0.0611 0.0601 0.0593 0.0366 0.0407
50℃ 0.0196 0.0289 0.0562 0.0579 0.0553 0.0572 0.0214 0.0268
Examples 9 to 13: oral care compositions
A1 mol/L sodium hydroxide solution and a 1mol/L pyrophosphoric acid solution were prepared, and the two solutions were mixed to prepare a buffer solution having a pH of 7.0.
The compositions of examples 9-13 were prepared as follows in Table 3:
table 3:
Figure BDA0001407464320000061
wherein the content of EGCg in the tea polyphenol material is 64.2%.
The stability test results for the compositions of examples 9-13 are shown in Table 4 below:
table 4: examples 9-13 EGCg assay (ppm) after 1 month aging of compositions
Example 9 Example 10 Example 11 Example 12 Example 13
25℃ 0 39 51 64 63
40℃ 0 19 29 59 61
50℃ 0 0 11 53 57
Example 14
A mouthwash formula comprises the following raw materials in percentage by weight:
Figure BDA0001407464320000062
Figure BDA0001407464320000072
wherein the content of EGCg in the tea polyphenol material is 64.2%.
The pH of the above formulation was 7.5. After being placed at 25 ℃ for one month, the content of EGCg can be detected to be 6 ppm.
Example 15
The toothpaste comprises the following raw materials in percentage by weight:
Figure BDA0001407464320000071
wherein the content of EGCg in the tea polyphenol material is 64.2%.
The above materials can be formed into oral care compositions, such as toothpastes, using methods conventional in the art.
The pH of the above formulation was 7.1. After one month at 25 ℃, the content of EGCg was 0.0613%.
Comparative examples 1 to 8:
chinese patent application CN10607419A discloses oral care compositions comprising free alkaline earth metal ions, stannous ions and polyphenols, which compositions may improve the stability of the polyphenols. Comparative examples 1-8 compare the effect of different pH on the stability of polyphenols in the compositions.
A1 mol/L sodium hydroxide solution and a 1mol/L pyrophosphoric acid solution were prepared, and the two solutions were mixed to prepare a buffer solution having a pH of 9.5.0, a pH of 7.50, a pH of 7.0, a pH of 6.5, a pH of 5.5, a pH of 4.5, a pH of 7.03.5, and a pH of 1.5, respectively.
Table 5: ingredient and raw material ratio tables for comparative examples 1-8 compositions
Figure BDA0001407464320000081
Wherein the content of EGCg in the tea polyphenol material is 64.2%.
TABLE 6 EGCg test results after 1 month aging (%), comparative examples 1-8 compositions
Figure BDA0001407464320000082
It follows that in oral care compositions comprising a stannous ion source and a polyphenol, in addition to alkaline earth metal ions (e.g. calcium ions) having a substantial effect on the stability of the composition, the pH range has a substantial effect on the stability of the composition.
It should be understood that the above-described embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. Not all embodiments are exhaustive. All obvious changes and modifications which are obvious to the technical scheme of the invention are covered by the protection scope of the invention.

Claims (11)

1. An oral care composition comprising a stabilized polyphenol characterized by: at least comprises a polyphenol compound and a stannous ion source, and the pH of the composition is 5-7.6; the polyphenolic compound comprises a compound of one or more of: epigallocatechin gallate and epicatechin gallate.
2. The oral care composition of claim 1, wherein: the composition has a pH of 6-7.
3. The oral care composition of claim 1, wherein: the composition further comprises a pH adjusting agent.
4. The oral care composition of claim 3, wherein: the pH regulator comprises one or more of sodium hydroxide, hydrochloric acid, sulfuric acid, citric acid and salts thereof, lactic acid and salts thereof, phosphoric acid and salts thereof, phthalic acid and salts thereof, pyrophosphoric acid and salts thereof, tripolyphosphoric acid and salts thereof, polyphosphoric acid and salts thereof, and acetic acid and salts thereof.
5. The oral care composition of claim 1, wherein: the polyphenol compound is tea polyphenol.
6. The oral care composition of claim 1, wherein: the stannous ion source is selected from one or more of stannous fluoride, stannous chloride, stannous pyrophosphate, stannous phosphate, stannous bromide, stannous iodide, stannous oxide, stannous sulfide, stannous metaphosphate, stannous acetate, stannous tartrate, stannous citrate, stannous malate, stannous malonate, stannous gluconate, and stannous oxalate.
7. The oral care composition of claim 1, wherein: the mass ratio of the stannous ion source to the polyphenol compound is more than 5: 1.
8. the oral care composition of claim 7, wherein: the mass ratio of the stannous ion source to the polyphenol compound is more than 10: 1.
9. the oral care composition of claim 8, wherein: the mass ratio of the stannous ion source to the polyphenol compound is more than 100: 1.
10. the oral care composition according to any one of claims 1 to 9, characterized in that: the polyphenol compound is added in the oral care composition in an amount of 0.0001-0.2 wt%.
11. The oral care composition according to any one of claims 1 to 9, characterized in that: the stannous ion source is added in the oral care composition in an amount of 0.001-1 wt%.
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WO2021062607A1 (en) * 2019-09-30 2021-04-08 The Procter & Gamble Company Oral care compositions comprising hops beta acid and amino acid
CN113384479B (en) * 2020-03-13 2023-07-21 好维股份有限公司 Oral care composition

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