WO2011115034A1 - 液体口腔用組成物及びその製造方法 - Google Patents

液体口腔用組成物及びその製造方法 Download PDF

Info

Publication number
WO2011115034A1
WO2011115034A1 PCT/JP2011/055888 JP2011055888W WO2011115034A1 WO 2011115034 A1 WO2011115034 A1 WO 2011115034A1 JP 2011055888 W JP2011055888 W JP 2011055888W WO 2011115034 A1 WO2011115034 A1 WO 2011115034A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
liquid oral
oral composition
composition
emulsion
Prior art date
Application number
PCT/JP2011/055888
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
祐司 新倉
隆 平山
Original Assignee
ライオン株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ライオン株式会社 filed Critical ライオン株式会社
Priority to JP2012505657A priority Critical patent/JP5690811B2/ja
Priority to CN201180015720.XA priority patent/CN102811702B/zh
Priority to KR1020127025933A priority patent/KR101790809B1/ko
Publication of WO2011115034A1 publication Critical patent/WO2011115034A1/ja

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • A61K8/375Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients

Definitions

  • the present invention relates to a non-ethanol type emulsified liquid oral composition and a method for producing the same that are excellent in appearance stability, have a good feeling in use in the oral cavity, and maintain a good refreshing feeling and staying feeling.
  • ethanol is blended in the liquid oral composition in order to give a refreshing feeling to use.
  • ethanol may be accompanied by irritation in the oral cavity, and for users who do not like irritation such as ethanol, non-ethanol preparations substantially free of ethanol have been developed and marketed.
  • non-ethanol preparations are inferior to refreshing use feelings, i.e., no stickiness, compared to ethanol-containing preparations due to the mild use feeling, and further, the effect feeling, i.e. the feeling of staying in the oral cavity of the preparation. It was inferior.
  • L-menthol In terms of a refreshing feeling, it can be imparted by blending ingredients such as L-menthol, but the blending effect with non-ethanol preparations is not sufficient, and the refreshing feeling after use is particularly poor. Further, L-menthol has a problem that a negative feeling of use such as irritation derived from menthol appears as the blending amount increases.
  • Patent Document 1 JP-A-2005-1792331
  • JP-A-2005-1792331 a technology has been proposed in which the effect is improved by blending a specific emulsion with a liquid oral composition containing ethanol
  • Patent Document 1 JP-A-2005-1792331
  • this technology is for ethanol blended preparations, and in non-ethanol preparations, there is a problem in that emulsion blending tends to cause oily sticky feeling derived from emulsion, resulting in marked stickiness and impaired usability. there were.
  • the emulsion is easily disintegrated, and it is difficult to maintain good appearance stability of the preparation.
  • Patent Document 2 Japanese Patent Laid-Open No. 2000-290151 describes the amount of menthol blended by combining a non-alcohol type or low alcohol type oral liquid composition with a specific taste agent and a cooling sensation agent. Although it is disclosed that at least a strong refreshing feeling is exhibited, it is difficult to say that this technique is sufficient to improve menthol stimulation. In addition, Patent Document 2 does not show the blending of the emulsion, and the appearance stability and usability of the emulsion blended preparation cannot be predicted from this technique.
  • a liquid oral composition that can maintain good appearance stability, has a mild and refreshing feeling without causing oily stickiness, and maintains an excellent refreshing feeling and staying feeling. Things are desired.
  • the present invention has been made in view of the above circumstances, has excellent appearance stability, has a mild and refreshing feeling without causing a sticky feeling when used in the oral cavity, and has an excellent refreshing feeling and a feeling of staying.
  • An object of the present invention is to provide a non-ethanol type liquid oral composition and a method for producing the same.
  • Non-ethanol type emulsified liquid that has excellent appearance stability, has no stickiness when used in the oral cavity, has a mild and refreshing feeling, and maintains a refreshing feeling and staying in the oral cavity after use. It has been found that an oral composition can be obtained.
  • liquid oral composition containing isopropylmethylphenol, a specific anionic surfactant, polyoxyethylene hydrogenated castor oil, and polyoxyethylene.
  • a liquid oral composition containing a nonionic surfactant selected from alkyl ethers and a wetting agent and having a water content of 70% by mass or more and containing no ethanol was proposed (Patent Document 3; International Publication No. 07). / 148551 pamphlet).
  • liquid oral composition containing isopropylmethylphenol and substantially no ethanol, polyoxyethylene hydrogenated castor oil having an average addition mole number of ethylene oxide of 40 to 100 moles, and decaglycerin.
  • An emulsified liquid oral cavity in which an emulsion having an average particle size of 50 to 500 nm composed of mono fatty acid ester, trifatty acid glyceryl, glycerin and water and a polyhydric alcohol selected from glycerin, propylene glycol and polyethylene glycol having an average molecular weight of 190 to 630 are blended.
  • a composition was proposed in PCT / JP2010 / 70070.
  • the emulsion is stably blended, the isopropyl methylphenol residual ratio in the oral cavity is high, and periodontopathic biofilm bactericidal power and high-temperature and low-temperature appearance stability can both be achieved.
  • periodontopathic biofilm bactericidal power and high-temperature and low-temperature appearance stability can both be achieved.
  • Applicants have further researched on non-ethanol type liquid oral compositions containing the above-mentioned emulsions, and techniques such as expression of stickiness when blending emulsions in non-ethanol preparations, weakness of coolness and retention
  • the technical problem is solved by blending L-menthol and 3- (L-menthoxy) propane-1,2-diol, and the feeling of use by combining the fragrance component (F) described later. It has been found that the retention feeling can be further improved and the present invention has been made.
  • a specific polyoxyethylene hydrogenated castor oil as a solubilizing agent and an emulsion of a specific average particle size composed of pre-decaglycerin monofatty acid ester, trifatty acid glyceryl, glycerin and water as an emulsifier are prepared.
  • An emulsion can be stably blended in a non-ethanol type liquid oral composition.
  • the mechanism of action is unclear, but the emulsion remains stable even when stored for about 3 months at high or low temperatures, which makes the emulsion unstable.
  • the color tone of the preparation is not faded or the oily component is separated and liquid-separated, the appearance stability of the preparation is excellent, and the oral retention feeling of the preparation is also improved.
  • ethanol is not blended and a large amount of surfactant does not have to be blended, so that it can be made into a mild preparation at the time of use, for example, mouthwash.
  • the present invention it is particularly important to improve the appearance stability and the retention in the oral cavity of a specific emulsion by combining a specific emulsion with a specific polyoxyethylene hydrogenated castor oil and a polyhydric alcohol in an appropriate combination.
  • the object of the present invention cannot be achieved even if an inappropriate emulsion is blended or any of the above essential requirements is lacking.
  • the present invention provides the following liquid oral composition.
  • Claim 1 To liquid oral composition substantially free of ethanol, (A) polyoxyethylene hydrogenated castor oil having an average addition mole number of ethylene oxide of 40 to 100 moles, (B) (B-1) decaglycerin monofatty acid ester, (B-2) trifatty acid glyceryl, (B-3) glycerin, and an emulsion having an average particle size of 50 to 500 nm, (C) L-menthol, (D) 3- (L-menthoxy) propane-1,2-diol, (E) A liquid oral composition comprising glycerin, propylene glycol, and at least one polyhydric alcohol selected from polyethylene glycol having an average molecular weight of 190 to 630.
  • a liquid oral composition comprising glycerin, propylene glycol, and at least one polyhydric alcohol selected from polyethylene glycol having an average molecular weight of 190 to 630.
  • Claim 2 The mass ratio of ⁇ (A) component and (B-1) decaglycerin monofatty acid ester ⁇ / ⁇ (B-2) trifatty acid glyceryl amount ⁇ is 0.77 to 1.87, and (E) The liquid oral composition according to claim 1, wherein the amount of the component is 5 to 15% by mass.
  • Claim 3 The total blending amount of the polyoxyethylene hydrogenated castor oil as the component (A) and the decaglycerin monofatty acid ester as the component (B-1) is 0.18 to 0.49% by mass of the whole composition.
  • Claim 4 The fatty acid of the decaglycerin monofatty acid ester of component (B-1) has 12 to 16 carbon atoms, and the fatty acid of the trifatty acid glyceryl of component (B-2) has 6 to 12 carbon atoms.
  • Claim 5 The liquid oral composition according to any one of claims 1 to 4, wherein the ethanol content in the composition is 100 ppm or less.
  • Claim 7 The liquid oral composition according to claim 6, wherein 0.001 to 500 ppm of component (F) is blended.
  • a method for producing the liquid oral composition Claim 9; The method according to claim 8, wherein the ethanol content in the composition is 100 ppm or less.
  • Claim 10 In addition to blending the above components (A), (C) to (E), (F) at least selected from violet extract, ⁇ -damasenone, benzyl alcohol, ⁇ -terpineol, methyl jasmonate, anise oil, and fennel oil The method according to claim 8 or 9, wherein the emulsion of the component (B) is added after blending one kind.
  • the non-ethanol type emulsifies with excellent appearance stability, has a mild and refreshing feeling without causing a sticky feeling when used in the oral cavity, and maintains an excellent refreshing feeling and staying feeling.
  • a liquid oral composition of the mold is obtained.
  • the following components (A) to (E) are blended with a liquid oral composition substantially free of ethanol, and more preferably the following component (F) is blended.
  • E glycerin, propylene glycol, and an average molecular weight of 190-
  • At least one polyhydric alcohol (F) violet extract selected from 630 polyethylene glycol, at least one selected from ⁇ -damasenone, benzyl alcohol, ⁇ -terpineol, methyl jasmonate, anise oil, and fennel oil
  • the component (A) polyoxyethylene hydrogenated castor oil has an average addition mole number of ethylene oxide of 40 to 100 moles, preferably 60 to 100 moles. When the average added mole number is less than 40 moles, the appearance stability is poor, and those exceeding 100 moles are generally not commercially available.
  • the blending amount of the component (A) is 0.15 to 0.40% (mass%, the same applies hereinafter) of the entire composition, particularly 0.20 to 0.00%, in terms of appearance stability and refreshing feeling. 30% is preferred. If the blending amount is less than 0.15%, the appearance stability may be inferior, and if it exceeds 0.40%, the sustainability of the refreshing feeling may be impaired.
  • the emulsion of component (B) is an emulsion having an average particle size of 50 to 500 nm, comprising (B-1) decaglycerin monofatty acid ester, (B-2) trifatty acid glyceryl, (B-3) glycerin, and water.
  • An oily component is tri fatty acid glyceryl
  • an aqueous component is water and glycerin, and it can mix using decaglycerin mono fatty acid ester which is a nonionic surfactant, and can prepare an emulsion.
  • the emulsion is obtained by dispersing water and (B-3) glycerin as a dispersion medium, and (B-2) trifatty acid glyceryl as an oil component in the presence of decaglycerin monofatty acid ester.
  • An O / W emulsion having an average particle size of 50 to 500 nm, wherein the oil droplet particles of the O / W emulsion are dispersed in the liquid oral composition, and the dispersion medium is dispersed in the aqueous phase of the liquid oral composition. It is integrated and dissolved, and exists as an O / W type emulsion in the liquid oral composition.
  • the decaglycerin monofatty acid ester having a fatty acid having 12 to 16 carbon atoms is suitable, and examples thereof include decaglyceryl monomyristate and decaglyceryl monolaurate.
  • the amount of decaglycerin monofatty acid ester is usually 5 to 15% in the emulsion. If it is less than 5%, the oily component is separated, and if it exceeds 15%, gelation may occur.
  • tri fatty acid glyceryl in the emulsion those having a carbon chain length of 6 to 12 are suitable, and examples thereof include glyceryl tricaprylate, glyceryl tricaprate, glyceryl tri (capryl / capric acid), and the like. More than seeds are used.
  • the amount of tri-fatty acid glyceryl is usually 40 to 60% in the emulsion. If it is less than 40%, an emulsion cannot be formed, and if it exceeds 60%, the oily component may be separated and the appearance stability may be impaired.
  • the amount of glycerin in the emulsion can be 1-30%, especially 10-20%. If it is less than 1%, uniform dissolution of the surfactant becomes complicated, and if it exceeds 30%, the oil component may be separated.
  • the average particle size of the emulsion is 50 to 500 nm, preferably 100 to 300 nm. When the average particle size is out of the above range, the appearance stability cannot be satisfactorily improved.
  • the measuring method of the average particle diameter of an emulsion is based on the method as described in the below-mentioned Example.
  • the form of the emulsion is an O / W type, and a known method can be adopted as the preparation method.
  • a predetermined amount of decaglycerin monofatty acid ester, glycerin and half amount of water can be prepared by stirring with a homomixer, adding trifatty acid glyceryl to form an emulsion, and finally adding the remaining water.
  • a method of adjusting the average particle diameter of the prepared emulsion using a high-pressure homogenizer can be preferably employed.
  • the target oral composition can be obtained by adding a predetermined amount of the emulsion thus prepared to the liquid oral composition.
  • commercially available products such as NET-TE-50 manufactured by Nikko Chemicals can be used.
  • the blending amount of the component (B) emulsion is 0.3 to 0.9%, particularly 0.4 to 0.4% of the total composition in terms of appearance stability, retention feeling, persistence of refreshing feeling, and lack of stickiness. 0.7% is preferable. If the blending amount is less than 0.3%, the color tone of the composition may fade (transparent) during high-temperature storage, the appearance stability may be impaired, and a sufficient staying feeling may not be obtained. If it exceeds 0.9%, the refreshing sensation, lack of stickiness, and appearance stability may be impaired.
  • the mass ratio of tri-fatty acid glyceryl ⁇ is preferably 0.77 to 1.87, and particularly preferably 1.00 to 1.20, whereby the appearance stability can be further enhanced.
  • the emulsion may collapse in low temperature (frozen) storage and the oil may be separated to impair appearance stability. If it exceeds 1.87, the color tone will fade in high temperature storage. , Appearance stability may be impaired.
  • the total amount of (A) component polyoxyethylene hydrogenated castor oil and (B-1) decaglycerin monofatty acid ester in component (B) is 0.18 to 0.49% of the total composition,
  • the content is preferably 0.2 to 0.37%, and by making the total blending amount in the above range, appearance stability and sustainability of a refreshing feeling can be further improved. If the blending amount is less than 0.18%, the oil may separate in the low temperature (frozen) storage to impair the appearance stability, and if it exceeds 0.49%, the refreshing feeling may be impaired.
  • Component (C) is L-menthol (CAS NO. (CAS registration number) 2216-51-5).
  • L-menthol CAS NO. (CAS registration number) 2216-51-5
  • menthol JP trade name
  • an essential oil containing L-menthol for example, essential oils such as peppermint oil (manufactured by Takasago International Corporation) and peppermint oil (manufactured by Toyo Hakkan Kogyo Co., Ltd.
  • L-menthol and an essential oil containing L-menthol are used in combination, a refreshing feeling is imparted and bitterness can be reduced.
  • (C) L-menthol is added in an amount of 0.001 to 1%, particularly 0.02 to 0.3% of the total composition in terms of sustaining a refreshing feeling, no stickiness, and no irritation of menthol. %, Particularly 0.05 to 0.2% is preferable. If it is less than 0.001%, sufficient sustainability of the refreshing feeling and lack of stickiness may not be obtained, and if it exceeds 1%, the bitterness and irritation of menthol may become strong, which may be undesirable in use.
  • the blending of 3- (L-menthoxy) propane-1,2-diol as component (D) with component (C) improves the refreshing feeling after use and maintains the refreshing feeling. And the non-stickiness of the preparation can be improved.
  • the 3- (L-menthoxy) propane-1,2-diol a commercially available product can be used, for example, cooling agent CA10 (trade name) manufactured by Takasago International Corporation.
  • Component (D) is blended in an amount of 0.0001 to 1%, particularly 0.001 to 0.2% of the total composition in terms of sustaining a refreshing feeling, no stickiness, and no menthol irritation. In particular, 0.005 to 0.1% is preferable. If it is less than 0.0001%, the sustainability of the refreshing feeling and the lack of stickiness may be impaired, and if it exceeds 1%, menthol irritation and bitterness may occur, which may be undesirable in use.
  • polyhydric alcohol of component (E) one selected from glycerin, propylene glycol, and polyethylene glycol having an average molecular weight of 190 to 630 is used alone or in combination of two or more.
  • the average molecular weight mentioned above shows the average molecular weight described in the Quasi-drug Raw Material Standard 2006, which is an average measured by reacting with phthalic anhydride in pyridine to form a phthalic acid ester and titrating with sodium hydroxide.
  • Molecular weight examples of polyethylene glycol having an average molecular weight of 190 to 630 include polyethylene glycol 200 (average molecular weight 190 to 210), polyethylene glycol 300 (average molecular weight 290 to 310), polyethylene glycol 400 (average molecular weight 390 to 410), polyethylene glycol 600 (590 to 610). ) Is applicable.
  • component (E) it is preferable to use 2 or more types of component (E) from the viewpoint of appearance stability and irritation during use, and more preferably 3 or more types.
  • component (E) As a combination of two kinds, a combination of glycerin, propylene glycol and polyethylene glycol 400 is preferable as a combination of three kinds of glycerin and polyethylene glycol 400.
  • the total amount of component (E) is preferably 5 to 15% of the entire composition in terms of appearance stability and no stickiness, and particularly preferably 6 to 13% in terms of appearance stability and no stickiness. If the blending amount is less than 5%, it may be difficult to maintain the appearance stability, and if it exceeds 15%, the color tone may fade and the appearance stability may be deteriorated or a sticky feeling may be produced.
  • component (E) glycerin should be blended at 0.5% or more of the entire composition
  • propylene glycol should be blended at 1% or more of the entire composition
  • polyethylene glycol having an average molecular weight of 190 to 630 should be blended at 1% or more of the entire composition. Is preferred.
  • Component (F) is composed of violet extract, ⁇ -damasenone (CAS NO. 23726-93-4), benzyl alcohol (CAS NO. 100-51-6), ⁇ -terpineol (CAS NO. 98-55-5) , One or more perfume ingredients selected from methyl jasmonate (CAS NO. 39924-52-2), anise oil, and fennel oil.
  • violet extract and ⁇ -damasenone are particularly preferred from the viewpoint of the absence of irritation of menthol and the persistence of the refreshing feeling.
  • (I) Violet extract The violet extract is obtained by distilling violet flower concrete, violet flower absolute, or oil obtained by distilling violet flower absolute, violet leaf concrete, violet leaf absolute, or violet leaf absolute. There are several types, such as oil, any of which can be used, but violet leaf absolute is particularly preferred among violet extracts.
  • the violet extract a commercially available product can be used. For example, a violet leaf absolute manufactured by Charabo Co., Ltd. or Ve Man Fis Fragrance Co., Ltd. can be used.
  • the extract is a plant body extracted with water and / or an organic solvent such as ethanol.
  • an organic solvent such as ethanol.
  • extract, oleoresin, resinoid, concrete, and absolute correspond to the extract, and these should be used.
  • a raw or dried plant may be used as it is, or a pulverized plant powder may be used as a raw material, and extraction may be performed under a normal condition by a known extraction method.
  • the extraction solvent is not particularly limited as long as it is used as a plant extraction solvent.
  • water, hexane, carbon dioxide, monohydric alcohol, polyhydric alcohol, or a mixture thereof can be used.
  • the solvent include lower monohydric alcohols such as water, methanol, ethanol, and isopropanol, and polyhydric alcohols such as ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, and 1,3-butylene glycol. Can be used singly or in combination of two or more.
  • the solvent extract can be used in the form of a solution as it is, but it is general to use an absolute obtained by distilling off the solvent and concentrating to an appropriate concentration. These may be used by lyophilization or the like and dried to remove the solvent, and may be used as it is, or may be used as it is or after adding an excipient or the like. A powdery product such as a freeze-dried product may be used by re-dissolving in a solvent and adjusting the concentration appropriately.
  • ⁇ -Damasenone (CAS No. 23726-93-4) Specifically, commercially available ⁇ -damasenone (manufactured by Iwata Fragrance Co., Ltd.) can be used.
  • Benzyl alcohol (CAS No. 100-51-6) Specifically, commercially available benzyl alcohol (manufactured by Iwata Fragrance Co., Ltd.) can be used.
  • ⁇ -Terpineol CAS No. 98-55-5) Specifically, commercially available ⁇ -terpineol (manufactured by Takasago International Corporation) can be used.
  • Methyl jasmonate (CAS No. 39924-52-2)
  • Examples of methyl jasmonate include methyl jasmonate, methyl dihydrojasmonate, methyl epijasmonate, and methyl epidihydrojasmonate, and any of them can be used.
  • Methyl epijasmonate is more preferred because it improves the refreshing feeling sustainability.
  • commercially available products such as methyl epijasmonate (manufactured by Iwata Fragrance Co., Ltd.) can be used.
  • anise oil As anise oil, it is possible to use an essential oil obtained from Pimpinella anisum, a magnolia family star anise (Illicium verum). The resulting essential oil can be used. As anise oil, a commercial item can be used, for example, a product made by Ve Man Fis Fragrance Co., Ltd. can be used.
  • fennel oil As the fennel oil, an essential oil obtained from fennel (Feniculum var. Vulgare) of the ciraceae family can be used. For example, an essential oil obtained by steam distillation of a ripe fruit can be used. Commercially available products can be used as the fennel oil, for example, Payan Bertrand S. A. Fennel oil made by the company can be used.
  • the essential oil as used herein refers to oil obtained by steam distillation from the whole plant or a plant such as flowers, fruits, leaves, stems, roots, seeds, and the like. Oil from which the reservoir has been removed may be used.
  • the blending amount is 0.001 to 500 ppm, particularly 0.01 to 100 ppm, especially 0.01, based on the whole composition from the viewpoint of non-irritating menthol and sustaining a refreshing feeling. ⁇ 10 ppm is preferred. If it is less than 0.001 ppm, the menthol irritation cannot be sufficiently suppressed, and the refreshing feeling may not be sufficiently maintained. If it exceeds 500 ppm, the sustainability of the refreshing feeling may be impaired.
  • the liquid oral composition of the present invention is substantially free of ethanol.
  • “substantially free of ethanol” means that the amount of ethanol in the composition is preferably 100 ppm or less, more preferably 50 ppm or less, particularly preferably 10 ppm or less, based on the total composition. The value is 0 ppm.
  • the liquid oral composition of the present invention contains no ethanol, but there are cases where a small amount of raw material-derived ethanol is contained in the fragrance compounded in the composition. In addition, it contains no ethanol other than a small amount of ethanol contained in the perfume.
  • the liquid oral cavity composition of the present invention can be prepared and applied as a mouthwash, liquid dentifrice, etc., depending on its dosage form, in addition to the above components, in addition to the above components
  • Appropriate known components can be blended.
  • a solvent, a wetting agent other than the polyhydric alcohol of component (E), a thickener, a surfactant other than the surfactant in component (A) and component (B), and if necessary, a pH adjuster, antiseptic Additives, sweeteners, fragrances other than the components (C), (D) and (F), active ingredients, colorants and the like can be contained.
  • wetting agent examples include sugar alcohols such as sorbitol, xylit, maltite, and lactit, and ethylene glycol.
  • sugar alcohols such as sorbitol, xylit, maltite, and lactit
  • ethylene glycol examples of the wetting agent.
  • xanthan gum sodium alginate, polyvinyl alcohol and the like can be contained within a range not impeding the effects of the present invention (the blending amount is usually 0 to 5%).
  • pH adjusters examples include phthalic acid, phosphoric acid, citric acid, succinic acid, acetic acid, fumaric acid, malic acid and carbonic acid and their potassium, sodium and ammonium salts, ribonucleic acid and its salts, and sodium hydroxide. Or a combination of phosphoric acid, citric acid and their sodium salts is particularly preferred.
  • the liquid oral composition of the present invention preferably adjusts the pH at 25 ° C. to 5.5 to 7.5, and sodium dihydrogen phosphate and sodium monohydrogen phosphate as pH adjusters in the vicinity thereof, Alternatively, it is preferable to use a combination of citric acid and sodium citrate.
  • purified water is usually used, and the blending amount is usually 60% or more.
  • paraoxybenzoic acid esters such as sodium benzoate, methylparaben, ethylparaben, propylparaben, butylparaben, alkyldiaminoethylglycine hydrochloride, potassium sorbate and the like can be contained.
  • saccharin sodium, stevocyte, sucralose, reduced palatinose, erythritol and the like can be contained as sweeteners.
  • natural essential oils such as spearmint oil, eucalyptus oil, winter green oil, clove oil, thyme oil, sage oil, cardamom oil, rosemary oil, marjoram oil, lemon oil, nutmeg oil, lavender oil, paracres oil, and the like
  • Fragrance components contained in the above natural essential oils such as L-carvone, 1,8-cineol, methyl salicylate, eugenol, thymol, linalool, limonene, menthone, menthyl acetate, citral, camphor, borneol, pinene, spirantol, etc.
  • Examples of the surfactant other than the nonionic surfactant contained in the component (A) and the component (B) include alkyl sulfates (for example, sodium lauryl sulfate, potassium lauryl sulfate, sodium myristyl sulfate, potassium myristyl sulfate, etc.) Alkali metal salts of alkyl sulfates having an alkyl group of 12 to 16), N-acyl amino acid alkali metal salts of 12 to 16 carbon atoms of acyl groups, lauroylmethyl taurine, acyl amino acid salts, sodium dodecylbenzenesulfonate, ⁇ - Anionic surfactants such as sulfofatty acid alkyl ester / sodium and alkyl phosphate ester salts, betaine acetate type amphoteric surfactants such as alkyldimethylaminoacetic acid betaine and fatty acid amidopropyldimethylaminoace
  • a surfactant other than the nonionic surfactant as the component (A) and the component (B), particularly a nonionic surfactant may not be added, and may be 0%. In this case, 0.01 to 1% of the entire composition is desirable.
  • Active ingredients include, for example, fungicides such as isopropylmethylphenol, tocopherol acetate, triclosan, cetylpyridinium chloride, anti-inflammatory agents such as tranexamic acid, epsilon-aminocaproic acid, dextranase, amylase, protease, mutanase, lysozyme, lysis Enzymes, enzymes such as lytechenzyme, fluorides such as sodium fluoride, sodium monofluorophosphate, stannous fluoride, vitamin C such as aluminum chlorohydroxy allantoin, allantoin, azulene, lysozyme chloride, ascorbic acid, dihydrocholesterol , Plant extracts such as glycyrrhetin salts, glycyrrhetinic acids, hydrocholesterol, chlorophyll, copper chlorophyllin sodium, thyme, ogon, clove, hamamelis,
  • these active ingredients can be mix
  • a colorant a highly safe water-soluble pigment such as Blue No. 1, Green No. 3, Yellow No. 4, Red No. 105 can be added.
  • PET polyethylene terephthalate
  • glass polypropylene
  • polyethylene polyethylene
  • the liquid oral composition of the present invention comprises a liquid oral composition substantially free of ethanol, (A) component polyoxyethylene hydrogenated castor oil, (C) component L-menthol, and (D) component. It can be produced by adding 3- (L-menthoxy) propane-1,2-diol and the polyhydric alcohol of component (E) and then adding the emulsion of component (B). Further, when the component (F) is blended, it is desirable to blend the components (A), (C) to (E) and the component (F) and then add the emulsion of the component (B).
  • polyoxyethylene (60) hydrogenated castor oil manufactured by Nikko Chemicals, average added mole number of ethylene oxide 60
  • POE (80) hydrogenated castor oil (manufactured by Nikko Chemicals) Average added mole number of ethylene oxide 80
  • emulsion average particle size 200 nm, NET-TE-50, manufactured by Nikko Chemicals
  • glycerin 100%, manufactured by Sakamoto Pharmaceutical Co., Ltd.
  • propylene glycol produced by Asahi Glass Co., Ltd.
  • Polyethylene glycol # 400 manufactured by Lion Chemical Co., Ltd.
  • citric acid manufactured by Fuso Chemical Co., Ltd.
  • sodium citrate manufactured by Fuso Chemical Co., Ltd.
  • polyoxyethylene (30) hydrogenated castor oil manufactured by Nikko Chemicals Co., Ltd., average added mole number of ethylene oxide 30
  • emulsion comparative examples. Further, the following components were used.
  • composition of emulsion (average particle size 200 nm)] Decaglyceryl monomyristate 10% Tri (Capryl / Capric Acid) Glyceryl 50 Glycerin 15 Water 25 Total 100%
  • composition and preparation method of comparative emulsion (average particle size 10 nm)] Decaglyceryl monolaurate 10% Olive oil 50 Glycerin 15 Water 25 Total 100% After pre-stirring glycerin, half amount of water and decaglyceryl monolaurate, olive oil was added and stirred with a homomixer, and finally the remaining water was added.
  • the average particle size of the emulsion was measured by the following method. [Measurement method of average particle diameter] Using a dynamic light scattering photometer N5 manufactured by BECKMAN COULTER, the emulsion was diluted 100 times with purified water, placed in a cell, and the average particle size at 25 ° C. was measured.
  • Appearance stability evaluation Fill the sample liquid oral composition into a 450 ml PET container (polyethylene terephthalate container, manufactured by Yoshino Kogyo) and store it in a 50 ° C thermostatic bath for 3 months or in a -10 ° C thermostatic bath for 3 months
  • the stability after storage was visually determined according to the following criteria in comparison with the control product (the product immediately after production in Example 1).
  • Evaluation criteria for appearance stability 50 ° C., 3 months
  • A No change is observed in the color tone of the preparation.
  • Although the fading of the color tone of the preparation is progressing slightly, it is a level at which there is no problem.
  • Fading of the color tone of the preparation is progressing.
  • X The color tone of the preparation is remarkably faded without comparison with the control product.
  • fading progresses is a state in which the color tone immediately after preparation of the preparation is white, and the color fades transparently, the cause of which is unknown in detail, This is considered to be solubilized by the free active agent.
  • Evaluation criteria for appearance stability ( ⁇ 10 ° C., 3 months) A : No change is observed.
  • Slight separation is observed, but there is no problem.
  • Separation is progressing.
  • X Considerable separation is observed, and the color tone of the preparation is also fading.
PCT/JP2011/055888 2010-03-19 2011-03-14 液体口腔用組成物及びその製造方法 WO2011115034A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2012505657A JP5690811B2 (ja) 2010-03-19 2011-03-14 液体口腔用組成物及びその製造方法
CN201180015720.XA CN102811702B (zh) 2010-03-19 2011-03-14 液体口腔用组合物及其制造方法
KR1020127025933A KR101790809B1 (ko) 2010-03-19 2011-03-14 액체 구강용 조성물 및 그 제조 방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010-064128 2010-03-19
JP2010064128 2010-03-19

Publications (1)

Publication Number Publication Date
WO2011115034A1 true WO2011115034A1 (ja) 2011-09-22

Family

ID=44649127

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2011/055888 WO2011115034A1 (ja) 2010-03-19 2011-03-14 液体口腔用組成物及びその製造方法

Country Status (5)

Country Link
JP (1) JP5690811B2 (zh)
KR (1) KR101790809B1 (zh)
CN (1) CN102811702B (zh)
MY (1) MY157740A (zh)
WO (1) WO2011115034A1 (zh)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013099621A1 (ja) * 2011-12-26 2013-07-04 ライオン株式会社 口腔用組成物
JP2014051445A (ja) * 2012-09-06 2014-03-20 Lion Corp 2層分離型液体口腔用組成物
JP2015205836A (ja) * 2014-04-21 2015-11-19 ライオン株式会社 液体口腔用組成物及び該組成物でのアラントイン又はその誘導体の低温安定化方法
JP2016150927A (ja) * 2015-02-19 2016-08-22 ライオン株式会社 口腔用組成物
KR20160145601A (ko) 2014-04-21 2016-12-20 라이온 가부시키가이샤 액체 구강용 조성물 및 그 동결 복원성 향상 방법
JP2017184636A (ja) * 2016-04-01 2017-10-12 長谷川香料株式会社 乳化組成物および粉末組成物
JP2019216614A (ja) * 2018-06-15 2019-12-26 国立研究開発法人農業・食品産業技術総合研究機構 メントールの刺激抑制剤および刺激抑制方法
JP2020070263A (ja) * 2018-11-01 2020-05-07 ライオン株式会社 液体口腔用組成物
JP2020105095A (ja) * 2018-12-27 2020-07-09 小林製薬株式会社 口腔用組成物

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2948676C (en) * 2014-05-15 2019-07-09 The Procter & Gamble Company Oral care compositions containing polyethylene glycol for physical stability
CN112675058A (zh) * 2020-12-31 2021-04-20 泰州市榕兴医疗用品股份有限公司 一种抑菌清凉的口腔清洁组合物及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09217083A (ja) * 1996-02-08 1997-08-19 Takasago Internatl Corp 清涼感改善剤
JP2000351988A (ja) * 1999-05-03 2000-12-19 Haarmann & Reimer Gmbh ミント及び/又はフルーツ香味組成物
JP2005179231A (ja) * 2003-12-18 2005-07-07 Lion Corp 液体口腔用組成物
WO2007148551A1 (ja) * 2006-06-23 2007-12-27 Lion Corporation イソプロピルメチルフェノール含有液体口腔用組成物
JP2008094772A (ja) * 2006-10-13 2008-04-24 Lion Corp 液体口腔用組成物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101098676B (zh) * 2004-12-22 2010-12-15 狮王株式会社 含有水解丝的口腔用组合物
JP4985905B2 (ja) 2005-07-29 2012-07-25 ライオン株式会社 液体口腔用組成物及びl−メントールの析出防止方法
TWI458495B (zh) * 2006-03-23 2014-11-01 Glaxosmithkline Llc 牙齒器具清潔劑
JP5196127B2 (ja) 2007-12-19 2013-05-15 ライオン株式会社 口腔用組成物
JP5397181B2 (ja) 2009-11-18 2014-01-22 ライオン株式会社 口腔スプレー用組成物及び口腔用製剤

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09217083A (ja) * 1996-02-08 1997-08-19 Takasago Internatl Corp 清涼感改善剤
JP2000351988A (ja) * 1999-05-03 2000-12-19 Haarmann & Reimer Gmbh ミント及び/又はフルーツ香味組成物
JP2005179231A (ja) * 2003-12-18 2005-07-07 Lion Corp 液体口腔用組成物
WO2007148551A1 (ja) * 2006-06-23 2007-12-27 Lion Corporation イソプロピルメチルフェノール含有液体口腔用組成物
JP2008094772A (ja) * 2006-10-13 2008-04-24 Lion Corp 液体口腔用組成物

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013099621A1 (ja) * 2011-12-26 2013-07-04 ライオン株式会社 口腔用組成物
JP2013133280A (ja) * 2011-12-26 2013-07-08 Lion Corp 口腔用組成物
JP2014051445A (ja) * 2012-09-06 2014-03-20 Lion Corp 2層分離型液体口腔用組成物
JP2015205836A (ja) * 2014-04-21 2015-11-19 ライオン株式会社 液体口腔用組成物及び該組成物でのアラントイン又はその誘導体の低温安定化方法
KR20160145601A (ko) 2014-04-21 2016-12-20 라이온 가부시키가이샤 액체 구강용 조성물 및 그 동결 복원성 향상 방법
JP2016150927A (ja) * 2015-02-19 2016-08-22 ライオン株式会社 口腔用組成物
JP2017184636A (ja) * 2016-04-01 2017-10-12 長谷川香料株式会社 乳化組成物および粉末組成物
JP2019216614A (ja) * 2018-06-15 2019-12-26 国立研究開発法人農業・食品産業技術総合研究機構 メントールの刺激抑制剤および刺激抑制方法
JP7261419B2 (ja) 2018-06-15 2023-04-20 国立研究開発法人農業・食品産業技術総合研究機構 メントールの刺激抑制剤および刺激抑制方法
JP7462238B2 (ja) 2018-06-15 2024-04-05 国立研究開発法人農業・食品産業技術総合研究機構 メントールの刺激抑制剤および刺激抑制方法
JP2020070263A (ja) * 2018-11-01 2020-05-07 ライオン株式会社 液体口腔用組成物
JP2020105095A (ja) * 2018-12-27 2020-07-09 小林製薬株式会社 口腔用組成物

Also Published As

Publication number Publication date
JP5690811B2 (ja) 2015-03-25
MY157740A (en) 2016-07-15
CN102811702B (zh) 2014-10-08
KR20130050282A (ko) 2013-05-15
CN102811702A (zh) 2012-12-05
KR101790809B1 (ko) 2017-11-20
JPWO2011115034A1 (ja) 2013-06-27

Similar Documents

Publication Publication Date Title
JP5690811B2 (ja) 液体口腔用組成物及びその製造方法
JP5624773B2 (ja) 口腔用組成物の製造方法
WO2013094504A1 (ja) 口腔用組成物
KR102345066B1 (ko) 액체 구강용 조성물 및 그 동결 복원성 향상 방법
JP2013107837A (ja) 液体口腔用組成物及び液体口腔用組成物における変色抑制方法
JP2005179231A (ja) 液体口腔用組成物
JP5753344B2 (ja) 口腔用組成物
JP5690744B2 (ja) 乳化型液体口腔用組成物及びその製造方法
JP2015089870A (ja) 液体口腔用組成物
JP5971988B2 (ja) 液体口腔用組成物
JP5825088B2 (ja) 液体口腔用組成物
CN110650720B (zh) 液体口腔用组合物
JP6610001B2 (ja) 液体口腔用組成物
WO2017209088A1 (ja) 口腔用組成物
JP7155943B2 (ja) 液体口腔用組成物及び口腔用スプレー製剤
JP2014214107A (ja) 歯磨組成物
CN111031999B (zh) 牙膏组合物
JP6331641B2 (ja) 液体口腔用組成物、その製造方法及び前記組成物でのアラントイン又はその誘導体の低温安定化方法
WO2022255124A1 (ja) 液体口腔用組成物
JP2023004666A (ja) 化粧料
JP2024030671A (ja) 口腔用組成物
JP2019210279A (ja) 練歯磨剤組成物
JP2020015702A (ja) 口腔用組成物
JP2020070263A (ja) 液体口腔用組成物
WO2018043275A1 (ja) 液体口腔用組成物

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201180015720.X

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11756219

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2012505657

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 1201004827

Country of ref document: TH

ENP Entry into the national phase

Ref document number: 20127025933

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 11756219

Country of ref document: EP

Kind code of ref document: A1