KR20150010550A - Compositions for oral-care - Google Patents

Abstract

The present invention relates to an oral-care composition. According to the present invention, the oral-care composition contains oral care components having a specific functional group which can covalently bond with a protein residue on the surface of oral organ, and forms covalent bond in oral organ without damage, thereby semipermanently providing the desired oral-care effect.

Description

[0001] Compositions for oral-care [0002]

The present invention relates to a reactive oral care component and a composition for oral care combined with a functional group binding to a protein.

Oral care is generally defined as oral care, which is applied, dispersed, or otherwise used in the oral cavity to clean and brighten the mouth and teeth, increase appeal, change appearance, or keep the mouth and teeth healthy , And the action is defined as being mild.

It is defined that quasi-drugs do not have the purpose of use, such as toothpaste and odorant mouth, but have a slight action and are not used for the treatment or prevention of disease, and affect the structure and function of the body .

Oral care or care products include functions such as toothpaste and toothpaste and mouthwashes such as mouthwash, tooth decay prevention, bad breath prevention, periodontal disease prevention, gum care, tongue care, prevention of tartar deposition, Orientation with orientation function Includes oral cavity.

Common raw materials used for constituting such mouthwashes include oily materials such as oil, wax, hydrocarbon, higher fatty acid, higher alcohol, ester oil and silicone oil, anion, cation, amphoteric, nonionic surfactant, moisturizer, An antioxidant, a metal ion blocking agent, a coloring material including a dye and a pigment, a perfume, a preservative, and the like, which are used as a thickening agent and a film forming agent.

 In addition, as the oral pharmaceutical ingredient for providing a special performance, sodium fluoride, sodium fluoride, sodium monofluorophosphate, chlorhexidine gluconate, cetylpyridinium chloride, isopropylmethylphenol, dextralase, mutagenase, A form in which allantoin and its derivatives, glycyrrhizic acid and its salts, ε-aminocaproic acid, tranexamic acid, dihydrocholesterol, azulene, ginseng extract, aluminum allantoin, Sodium chloride, pyridoxine chloride, sodium chlorophosphate, sodium polyphosphate, zeolite, polyethylene glycol, enzymes, hormones, amino acids, and natural products derived from natural sources.

However, in the case of care or management of the oral cavity and teeth with such ingredients for oral cavity and medicines, there is always a need to provide a temporary effect only until the next cleaning after the composition treatment, Document 1].

Korea Patent Publication No. 2013-0116486

It is an object of the present invention to provide a composition for oral care which can continuously provide a permanent oral care effect without damaging teeth or gums.

As a means for solving the above problems, the present invention provides a composition for oral care comprising a carbodiimide compound and a mouth care component.

As another means for solving the above problems, the present invention provides a composition for oral care comprising at least one compound selected from the group consisting of carbodiimide, imido ester, aryl azide, diazirine, hydroxymethylphosphine, pentafluorophenyl ester, pyridyl disulfide, At least one tooth selected from the group consisting of hydroxysuccinimide ester, alkoxyamine, hydrazide, haloacetyl, and azide, and a functional group that is covalently bonded to the protein on the surface of the gum.

As another means for solving the above problems, the present invention provides a composition for oral care comprising the reactive oral care component.

The composition for oral care according to the present invention contains a reactive oral care component and / or a carbodiimide compound into which a specific functional group capable of covalent bonding with a protein moiety of the oral cavity or teeth is incorporated, thereby forming a covalent bond without damaging the oral cavity Thus providing a permanent oral care effect.

The present invention relates to a composition for oral care comprising a carbodiimide compound and an oral care ingredient.

The composition for oral care according to the present invention can be prepared, for example, by reacting a carbodiimide compound with a known oral care ingredient to form a covalent bond with the protein of teeth or gums through a reactive oral care ingredient having a carbodiimide group To maximize the oral care effect.

The carbodiimide compound may be used in an amount of 0.001 to 10 parts by weight, 0.01 to 7 parts by weight, or 0.1 to 5 parts by weight based on 100 parts by weight of the total composition. If the content is less than 0.001 part by weight, the amount of the covalent bond is too small to exhibit a substantial effect and a continuous effect is difficult to be exhibited. If the content is more than 10 parts by weight, A carbodiimide compound does not react with the skin in a state where it does not react with the skin, thereby failing to improve persistence and acting as a lost ingredient.

In the present invention, the 'oral care effect' is a function of cleansing, grooming, attracting, or maintaining and managing healthy oral tissues such as gums, teeth, and tongue, (Prevention) or improvement of periodontal disease.

As used herein, "oral care composition" is intended not to be intentionally swallowed for systemic administration of a therapeutic agent but to retain within the mouth for a period of time sufficient to contact virtually all of the tooth surface and / Of the product. The term may also refer to a product which may be intentionally swallowed but which can not be swallowed for systemic administration of the therapeutic agent. Such oral care compositions include toothpastes, gels, rinses, edible films, and lozenges.

The oral care ingredient used in the present invention may be an oily ingredient such as oil, wax, hydrocarbon, higher fatty acid, higher alcohol, ester oil, silicone oil, anion, cation, Antioxidants, metal ion sequestrants, colorants including dyes and pigments, fragrances, preservatives, and the like. Examples of the component having an oral care function include sodium fluoride, sodium fluoride, sodium monofluorophosphate, chlorhexidine gluconate, cetylpyridinium chloride, isopropylmethylphenol, dextralase, mutagenase, A form in which allantoin and its derivatives, glycyrrhizic acid and its salts, ε-aminocaproic acid, tranexamic acid, dihydrocholesterol, azulene, ginseng extract, aluminum allantoin, aluminum lactate, A derivative thereof, sodium chloride, pyridoxine chloride, sodium chlorophyllin, sodium polyphosphate, zeolite, polyethylene glycol, enzymes, hormones, amino acids and natural products.

The oral care ingredient is preferably used in an amount of 0.001 to 50 parts by weight, 0.001 to 30 parts by weight, 0.01 to 10 parts by weight, or 0.1 to 5 parts by weight based on 100 parts by weight of the total composition. When the content is less than 0.001 part by weight, the effect of the active ingredient is limited. When the content exceeds 50 parts by weight, there is a problem that it acts as a component that can not be stabilized and reacted with time in formulation and formulation.

Particularly, in the present invention, the oral care component can increase the reaction efficiency with the carbodiimide compound by including a carboxyl group or an amine group in the molecule.

In addition, in the present invention, the oral care component may have a functional group capable of covalent bonding with protein residues on the oral cavity surface.

The functional group covalently bonded to the protein is selected from imide ester, aryl azide, diazyline, hydroxymethylphosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxy succinimide ester, alkoxyamine, hydrazide, The present invention relates to a process for the preparation of a compound of formula (I) as defined in claim 1, wherein the compound is selected from the group consisting of: haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, But are not limited to, at least one selected from the group consisting of oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone Do not.

In addition, the protein may comprise reactive residues of thiol, hydroxyl, carboxyl or amine.

The carbodiimide compound is generally referred to as a compound containing a structure represented by the following formula (1) in the molecule.

[Chemical Formula 1]

-N = C = N-

The carbodiimide compound preferably has at least 1 to 1000 structures represented by the formula (1), more preferably 1 to 100 structures represented by the formula (1) It is more preferable that the structure includes 1 to 10 structures in the molecule.

In this case, if the number of the carbodiimide groups represented by the formula (1) exceeds 1,000 in one molecule, the viscosity of the starting material is too large, the molecular weight is excessively large, the reaction position where the reaction can be performed becomes excessively large, The molecule having the bodymide group becomes too large, and the efficiency is lowered by blocking the portion showing the functional effect of the molecule having the substantial function.

In the present invention, a specific example of the carbodiimide compound may be a compound represented by the following formula (2), wherein n is 4 and m is 11 in the following formula (2): benzene, 1,3, Isocyanato-1-methylethyl) -, homopolymer, polyethylene glycol mono-ether-block (benzene, 1-isocyanato- Me-ether-blocked (hereinafter referred to as polymeric carbodiimide compound of formula (2)).

(2)

In the above formula (2), n is 1 to 100 and m is 1 to 100.

Another example of the carbodiimide compound in the present invention is 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, which is a compound represented by the following formula (3) carbodiimide or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl may be used.

(3)

In one preferred embodiment of the composition for oral care according to the present invention, the oral care ingredient having a carboxyl group is made into a form of a reactive ester oral care ingredient having a direct bioreactivity, or an amino acid excessive in an oral cavity (15.5 to 23.5% (ex., aspartic acid, glutamic acid) is reacted with a carbodiimide compound capable of targeting an oral care component containing an amine group to increase the reaction efficiency by producing an ester form (reactive oral care component) having a reactivity The effect can be remarkably increased. In addition, it is also possible to use carbodiimides, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy The effect of the oral care component containing a functional group such as amine, hydrazide, haloacetyl, or azide in the molecule can be further increased.

In a more preferred embodiment, the polymeric carbodiimide compound of formula (2) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide is first added to the surface of the oral care component molecule or oral cavity organ with a carboxyl group. A carbodiimide compound such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl is firstly reacted to form a reactive ester, and an oral care ingredient having an amine in its molecule in addition to the reactive ester functional group formed Or by reacting with an amine on the surface of the oral cavity, an excellent oral care effect can be obtained. The reaction is preferably carried out at a pH of 2 to 10, more preferably at a pH of 3 to 9, most preferably at an acidic to slightly acidic pH of about 4 to 5 The reaction efficiency can be increased most. The reaction is completed within 1 minute to 30 minutes.

In the following Reaction Scheme 1, the oral care component molecule having a carboxyl group reacts with a carbodiimide compound to form a reactive ester, and then reacts with an amino acid having an amine residue to form a covalent bond.

[Reaction Scheme 1]

In the following Reaction Scheme 2, asparaginic acid and glutamic acid, which are bioamino acids having a carboxyl group on the surface of the protein of the oral cavity (oral + tooth), react first reaction with a carbodiimide compound to form a reactive ester, followed by reaction with an oral care component having an amine residue To form a covalent bond.

[Reaction Scheme 2]

The carbodiimide compound increases the reaction efficiency between the protein of the oral cavity and the oral care component, so that the reactive oral care ingredient bound to the oral cavity does not fall off well during general oral cleaning due to toothpaste, toothpaste, goggles, etc., So that it can remain attached to the oral cavity.

The present invention also relates to the oral care composition comprising at least one compound selected from the group consisting of carbodiimide groups, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, The present invention relates to a process for the preparation of a pharmaceutical composition which comprises administering an effective amount of a compound selected from the group consisting of an amine, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, At least one member selected from the group consisting of diesters, imidazoles, oxycarbonylamidazoles, imines, thiols, maleimides, vinylsulfones, ethyleneimines, thioethers, acrylonitriles, acrylic acid or methacrylic acid esters, disulfides and ketones May contain a reactive oral care component with a functional group covalently bonded to the protein have.

For example, as shown in Reaction Scheme 1, a carbodiimide compound may be bonded to a carbodiimide group to form an oral care component. In addition, the present invention may include a composition for oral care comprising the reactive oral care component.

In order to enhance the secondary effects of the composition for oral care according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, and cationic quaternary alkyl quaternary ammonium salts such as linear and branched long chain alkyl quaternary ammonium salts When mixed with a cationic polymer such as a surfactant, cationized cellulose, cationic guar, cationized polyvinylpyrrolidone, silicone, etc., formulation can be facilitated. In addition, for formulation, auxiliary ingredients such as a solvent, a surfactant, a thickener, a stabilizer, a preservative, a colorant, a pH adjuster, a sequestering agent, a colorant, a pearlizing agent, can do. The ingredients for the formulation may be used in an amount of 40 to 99 parts by weight based on 100 parts by weight of the total composition.

The composition for oral care according to the present invention can be used for prescription of a cosmetic composition for oral care including a component having an oral care function having a functional group. Application examples of oral products may include all formulations, such as, for example, dentifrices, chewable toothpaste, gels, rinses, edible films, candies, sugars, gums and lozenges.

More preferably, the oral care composition according to the present invention comprises a carbodiimide-based compound and at the same time an oral care component having a reactive functional group. When the activity of the above-mentioned preparation is lowered in the aqueous system, It may be easier to maintain the activity in the buffer solution before the reaction, or may be mixed with a buffer for pH control just before use, or may be brought into contact with water during the washing process. Examples of non-aqueous formulations include liquid, sheet, powder, tablet, oil, wax, ampoule, gel and the like which are used as ordinary non-aqueous cosmetic preparations. In addition, the carbodiimide compound and the oral care ingredient can be formulated as a single agent in encapsulated form or in two separate forms, respectively. In addition, a method of blocking a derivative in which a functional group having a reactivity and a component having an oral care function are combined through encapsulation from moisture can also be used.

In order to enhance the oral care effect of a functional oral care composition according to the present invention, it is preferred to use 2-basic acid esters such as dioctylsuccinate, dioctyl adipate, diethyl sebacate and the like, polyols, polyethylene glycol, propylene glycol , Hexylene glycol, butane diol and their isomers, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof. The above-mentioned solvents increase the permeability of the oral cavity and are used as a solvent for a poorly soluble substance. More preferably, the solvent used for increasing the activity maintaining effect of the oral care ingredient having a functional group is diethyl sebacate, ethoxy glycol, bis-ethoxy glycol cyclohexane 1,4-dicarboxylate, and the like.

Hereinafter, the present invention will be described in detail by the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.

Example  1 to 4 and Comparative Example  1 to 2

An oral dentifrice composition was prepared by using ε-aminocaproic acid and trienamic acid containing a carboxyl group and an amine group in the molecule while being effective in improving gum bleeding.

Sorbitol was added to the buffer solution (pH 4.5) by the composition and content as shown in Table 1 below, and ε-aminocaproic acid and trinechemic acid were added, respectively. Sodium fluorophosphate, sodium saccharin and sodium salt of alginic acid, in which the preservative was dissolved and dispersed in glycerin, were added thereto. To the composition, calcium carbonate, fragrance and lauryl glucoside were further added to prepare an oral dentifrice composition.

Category (% by weight) Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Example 4 Sodium saccharin 0.2 0.2 0.2 0.2 0.2 0.2 Sodium fluorophosphate 1.0 1.0 1.0 1.0 1.0 1.0 antiseptic 0.1 0.1 0.1 0.1 0.1 0.1 Sorbitol 35.0 35.0 35.0 35.0 35.0 35.0 glycerin 7.0 7.0 7.0 7.0 7.0 7.0 Sodium alginate 0.5 0.5 0.5 0.5 0.5 0.5 Calcium carbonate 20.0 20.0 20.0 20.0 20.0 20.0 Lauryl glucoside 3.0 3.0 3.0 3.0 3.0 3.0 Spices 0.2 0.2 0.2 0.2 0.2 0.2 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride - - 1.0 1.0 - - Benzene, 1,3, -bis (1-isocyanato-1-methylethyl) -, homopolymers, polyethylene glycol mono-ether- - - - - 1.0 1.0 ? -aminocaproic acid 1.0 - 1.0 - 1.0 - Tranexamic acid - 1.0 - 1.0 - 1.0 The buffer (pH 4.5) 32.0 32.0 31.0 31.0 31.0 31.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0

Experimental Example  One

After the dentifrice compositions of Comparative Examples 1 to 2 and Examples 1 to 4 were applied to the applicants having 10 gum bleeding problems for each composition for 3 or more times a day for 10 days, 5 points scale (5 points with better effect), and the results are shown in Table 2.

In comparison with the results (Table 2) of Examples 1 to 4 and Comparative Examples 1 and 2 and Comparative Examples 1 and 2 which did not include carbodiimide, Examples 1 to 4 including carbodiimide were found to share carbodiimide Binding formation effect showed better gingival bleeding effect.

Claims (9)

Carbodiimide compounds; And oral care ingredients.
The method according to claim 1,
Wherein the oral care component comprises a carboxyl group or an amine group in the molecule.
The method according to claim 1,
Wherein the oral care component is selected from the group consisting of sodium fluoride, tin fluoride, sodium monofluorophosphate, chlorhexidine gluconate, cetylpyridinium chloride, isopropylmethylphenol, dextralase, mutagenase, histoxiol, allantoin and its derivatives, Glycyrrhizic acid and its salts, ε-aminocaproic acid, tranexamic acid, dihydrocholesterol, azulene, angelica extract, aluminum allantoin, aluminum lactate, vitamin E and derivatives, sodium chloride, pyridoxine chloride, Sodium, zeolite, polyethylene glycol, enzymes, hormones, amino acids, and natural products.
The method according to claim 1,
Wherein the oral care ingredient has a functional group capable of covalently bonding to protein residues on the surface of the oral cavity.
5. The method of claim 4,
The functional group covalently bonded to the protein is selected from imide ester, aryl azide, diazyline, hydroxymethylphosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxy succinimide ester, alkoxyamine, hydrazide, The present invention relates to a process for the preparation of a compound of formula (I) as defined in claim 1, wherein the compound is selected from the group consisting of: haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, Wherein the composition is at least one selected from the group consisting of oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone.
The method according to claim 1,
Wherein the carbodiimide compound is 0.001 to 10 parts by weight per 100 parts by weight of the total composition.
The method according to claim 1,
A carbodiimide compound and an oral care ingredient are formulated into a single preparation in encapsulated form; Wherein the carbodiimide compound and the oral care ingredient are separated from each other.
The oral care component may further comprise at least one compound selected from the group consisting of carbodiimide, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, , Haloacetyl, and azide. ≪ RTI ID = 0.0 > A < / RTI >
A composition for oral care comprising a reactive oral care ingredient according to claim 8.