WO2021200393A1 - Cosmetic - Google Patents

Cosmetic Download PDF

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Publication number
WO2021200393A1
WO2021200393A1 PCT/JP2021/011945 JP2021011945W WO2021200393A1 WO 2021200393 A1 WO2021200393 A1 WO 2021200393A1 JP 2021011945 W JP2021011945 W JP 2021011945W WO 2021200393 A1 WO2021200393 A1 WO 2021200393A1
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Prior art keywords
cosmetic
present
fatty acid
antiseptic
cosmetics
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PCT/JP2021/011945
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French (fr)
Japanese (ja)
Inventor
達也 川口
江利子 横田
チンエク アン
Original Assignee
株式会社 資生堂
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Application filed by 株式会社 資生堂 filed Critical 株式会社 資生堂
Priority to CN202180018081.6A priority Critical patent/CN115209865A/en
Publication of WO2021200393A1 publication Critical patent/WO2021200393A1/en

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Classifications

    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to a cosmetic having a high antiseptic effect.
  • cosmetics are used for a long time after opening, it is indispensable to have an antiseptic effect to suppress the growth and reproduction of microorganisms. Therefore, it is common for cosmetics to contain parabens such as methylparaben and ethylparaben and preservatives such as phenoxyethanol.
  • parabens such as methylparaben and ethylparaben
  • preservatives such as phenoxyethanol.
  • additive-free cosmetics tend to be preferred as cosmetics, and cosmetics containing no preservatives are required as one of the additives. Therefore, a technique for imparting an antiseptic effect to cosmetics has been developed in place of the conventional preservatives for cosmetics.
  • Patent Document 1 (A) 0.2% by mass or more of n-hexyl 2,2-bis (hydroxymethyl) propionic acid, (B) a polyhydric alcohol having 3 to 9 carbon atoms, and 6 to 8 carbon atoms. It is described that a skin external preparation having an antiseptic and antibacterial effect can be obtained by combining one or more selected from alkyl glyceryl ether and fatty acid glyceryl ester having 8 to 12 carbon atoms in a specific ratio.
  • divalent glycols such as dipropylene glycol and 1,3-butylene glycol are highly safe moisturizers and are widely blended in cosmetics, but are known to have antibacterial activity.
  • divalent glycols such as dipropylene glycol and 1,3-butylene glycol
  • An object of the present invention is to provide a cosmetic having a high antiseptic effect against fungi and bacteria.
  • the present invention (A) Fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) Acetophenone derivative represented by the following formula (1).
  • R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group
  • the cosmetic of the present invention can obtain a cosmetic having a high antiseptic effect against fungi and bacteria. Since a sufficient antiseptic effect can be obtained from the components (A) and (B), it is not necessary to add a high amount of divalent glycol or lower alcohol in order to obtain the antiseptic effect, and it is sticky and irritating to the skin. It is possible to obtain a cosmetic having a good feeling of use. In addition, preservative-free cosmetics that do not contain preservatives that are usually used in cosmetics can be realized.
  • the cosmetic of the present invention is characterized by containing (A) a fatty acid glyceryl ester having 8 to 12 carbon atoms and (B) a specific acetophenone derivative.
  • the combination of the component (A) and the component (B) imparts an antiseptic effect to the cosmetic.
  • each component constituting the cosmetic of the present invention will be described in detail.
  • the (A) fatty acid glyceryl ester (hereinafter, may be simply referred to as “component (A)”) blended in the cosmetic of the present invention is a fatty acid glyceryl ester usually blended in cosmetics and has a carbon number of carbon. It is from 8 to 12. Examples include glyceryl caprylate, glyceryl 2-ethylhexanoate, glyceryl caproate, glyceryl undecylenate, glyceryl laurate and the like.
  • one or more of the above fatty acid glyceryl esters may be used as the component (A).
  • the lower limit of the amount of the component (A) is preferably 0.01% by mass or more or 0.05% by mass or more, and the upper limit is 0.4% by mass or less or 0. It is preferably 3% by mass or less. Therefore, preferred compounding amount ranges include 0.01 to 0.4% by mass, 0.01 to 0.3% by mass, 0.05 to 0.4% by mass, 0.05 to 0.3% by mass, and the like. .. If the blending amount is less than 0.01% by mass, sufficient antiseptic / antibacterial action may not be obtained, and if the blending amount exceeds 0.4% by mass, the skin may be irritated.
  • the (B) acetophenone derivative (hereinafter, may be simply referred to as “component (B)”) blended in the cosmetic of the present invention is an acetophenone derivative usually blended in cosmetics and has the following formula (1). ) Or a salt thereof.
  • R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group, and R 1 and R 2 are arranged at the ortho, meta or para position with respect to the acetyl group.
  • the compound is one or more selected from the group consisting of the following compounds.
  • 4-hydroxyacetophenone is more preferable in the present invention.
  • the salt of the compound represented by the above formula (1) may be a cosmetically acceptable salt or a pharmaceutically acceptable salt, and examples thereof include sodium salt, potassium salt, ammonium salt and the like.
  • the lower limit of the amount of the component (B) is preferably 0.06% by mass or more or 0.1% by mass or more, and the upper limit is 2.0% by mass or less or 1. It is preferably 0% by mass or less. Therefore, preferred compounding amount ranges include 0.06 to 2.0% by mass, 0.06 to 1.0% by mass, 0.1 to 2.0% by mass, 0.1 to 1.0% by mass, and the like. .. If the blending amount is less than 0.06% by mass, sufficient antiseptic / antibacterial action may not be obtained, and if the blending amount exceeds 2.0% by mass, the skin may be irritated.
  • antibacterial means suppressing the growth of bacteria on the surface of an object
  • antiseptic means suppressing the invasion, growth and growth of microorganisms, causing putrefaction and fermentation. Means not to. Therefore, the "antiseptic effect” or “antiseptic effect” in the present invention refers to an effect including both “antibacterial” and “antiseptic”, and when the object is a cosmetic, fungi, yeast and the like in the cosmetic. It means the effect of suppressing the growth of fungi such as molds, preventing the deterioration of cosmetics by bacteria, and improving the storage stability of cosmetics.
  • the fatty acid glyceryl ester has a strong antiseptic effect on yeast and bacteria and has a weak antiseptic effect on mold
  • the acetophenone derivative has a strong antiseptic effect on mold and against yeast and bacteria. It became clear that the antiseptic effect was weak.
  • phenoxyethanol which is usually used as an antiseptic in cosmetics, has a strong antiseptic effect on Pseudomonas aeruginosa, but is inferior in antiseptic effect on other bacteria, yeast and mold.
  • the combination of a fatty acid glyceryl ester and an acetophenone derivative provides a high antiseptic effect against all of molds, yeasts and bacteria without canceling each other's advantages, and is a novel combination having a broad antibacterial spectrum. Was able to be realized.
  • Patent Document 1 describes that the fatty acid glyceryl ester according to the present invention exhibits an antiseptic and antibacterial effect in combination with n-hexyl 2,2-bis (hydroxymethyl) propionic acid.
  • the acetphenone derivative according to the present invention is an acyl amino acid such as acylproline (eg, decanoylproline) and acylglycine (eg, octanoylglycine, undecilenoylglycine) in Patent Document 2 (Japanese Patent Laid-Open No. 2018-90579). It is described that the combination of and polyhydric alcohol has an antiseptic effect on bacteria and fungi.
  • the cosmetic of the present invention may contain various components that are usually blended as cosmetics.
  • hydrocarbon oils higher fatty acids, higher alcohols, synthetic ester oils, silicone oils, liquid fats and oils, solid fats and oils, oils such as wax, UV protective agents, oil phase thickeners, and surfactants that are usually used in cosmetics.
  • Water lower alcohol, polyhydric alcohol, water-soluble polymer, moisturizer, powder, coloring material, fragrance, neutralizer, chelating agent, pH adjuster, vitamins, antioxidants, chemicals, etc. as needed Including.
  • the (A) fatty acid glyceryl ester and the (B) acetophenone derivative provide a sufficient antiseptic effect, so that it is not necessary to add phenoxyethanol and parabens, which are usually used in cosmetics, as preservatives. Therefore, aspects of the present invention include aspects that do not contain phenoxyethanol and / or parabens. According to the present invention, a preservative-free cosmetic, that is, a "preservative-free" cosmetic can be realized.
  • divalent glycols such as dipropylene glycol and 1,3-butylene glycol may be blended in an amount of more than 10% by mass based on the total amount of cosmetics.
  • the blending amount of the divalent glycol can be reduced to 10% by mass or less. Therefore, the aspect of the present invention includes an aspect in which the blending amount of the divalent glycol is 10% by mass or less.
  • the amount of lower alcohol such as ethanol may be increased to obtain an antibacterial effect.
  • the blending amount of the lower alcohol can be set to 3% by mass or less. Therefore, the aspect of the present invention includes an aspect in which the blending amount of the lower alcohol such as ethanol is 10% by mass or less or 3% by mass or less, and a mode in which the lower alcohol is not blended. By reducing the amount of the lower alcohol blended, it is possible to obtain a cosmetic product in which irritation to the skin is sufficiently suppressed.
  • the blended object has excellent antiseptic activity against fungi such as bacteria, yeast and mold. show. Therefore, according to the present invention, by blending the components (A) and (B) according to the present invention with the antiseptic object, the antiseptic power of the antiseptic object against bacteria and fungi can be enhanced. can.
  • the antiseptic object is not limited to cosmetics, and examples thereof include skin external preparations such as ointments, fragrance products such as perfumes and colons, daily hygiene products such as sweat wipes, and baby hygiene products such as wipes. NS.
  • the present invention comprises (A) a fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) an acetophenone derivative represented by the following formula (1).
  • the present invention relates to a method for enhancing the antiseptic activity against fungi and bacteria, including the addition of the above into an antiseptic object.
  • the preservative object is a cosmetic.
  • the components (A) and (B) according to the present invention may be added to the finished product of the antiseptic object, or may be blended during the manufacturing process of the antiseptic object.
  • the component (A) and the component (B) may be blended at the same time or separately. When blended separately, either component (A) or component (B) may come first.
  • the dosage form of the cosmetic according to the present invention is not particularly limited, and any dosage form of ordinary cosmetics can be used. That is, liquid, gel, paste, milky, cream, spray and the like can be used.
  • the cosmetics according to the present invention are not particularly limited, and include skin care cosmetics such as lotions and moisturizing creams, makeup cosmetics such as foundations, BB creams, eye shadows, and lipsticks, sunscreen cosmetics, and packs. Can be blended.
  • skin care cosmetics such as lotions and moisturizing creams
  • makeup cosmetics such as foundations, BB creams, eye shadows, and lipsticks
  • sunscreen cosmetics and packs. Can be blended.
  • the present invention exerts an antiseptic effect on fungi and bacteria by the combination of the (A) fatty acid glyceryl ester and the (B) acetphenone derivative, a wide range including fungi and bacteria is described in the present invention.
  • An antiseptic composition having an antibacterial spectrum can be obtained. That is, the present invention comprises (A) a fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) an acetophenone derivative represented by the following formula (1).
  • R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group
  • the present invention will be described in more detail with reference to examples below, but the present invention is not limited thereto.
  • the blending amount is shown in mass% with respect to the system in which the component is blended.
  • the lotions of Test Examples 1 to 5 having the compositions shown in Table 1 were prepared by a conventional method, and an antiseptic effect test and a use test were carried out.
  • Fungi to be tested Ps: Pseudomonas aeruginosa (strain name: Pseudomonas aeruginosa, ATCC15442)
  • E Escherichia coli (strain name: Escherichia coli, ATCC8739)
  • S Staphylococcus aureus (strain name: Staphylococcus aureus, ATCC6538)
  • Asp Black mold (strain name: Aspergillus brasiliensis, ATCC16404)
  • the antiseptic effect was evaluated according to the following criteria, and only those that were judged as A were judged to have sufficient antiseptic power. Evaluation Criteria for Antiseptic Effect on Ps, E, S A: LRV was 3 or higher after 7 days. B: It took 8 to 14 days for the LRV to show 3 or higher. C: The LRV was less than 3 even after 14 days or more. Evaluation Criteria for Antiseptic Effect on Can A: LRV was 1 or higher after 7 days. B: It took 8 to 14 days for the LRV to show 1 or higher. C: The LRV was less than 1 even after 14 days or more. Evaluation Criteria for Antiseptic Effect on ASP A: LRV was 1 or higher after 14 days. B: It took 15 to 28 days for the LRV to show 1 or higher. C: The LRV was less than 1 even after 28 days or more.
  • ⁇ Usability test> Ten panelists were asked to use the drug twice a day for a week, and they were asked to report the satisfaction of the feeling of use and the presence or absence of skin irritation. The evaluation of usability was classified into the following four criteria, and the number of people who complained of irritation was confirmed. A: 8 or more panelists who have no skin irritation and feel good to use B: 5 or more to less than 8 panelists who have no skin irritation and feel good to use C: No skin irritation and use 3 or more to less than 5 panelists who found it to be comfortable D: Less than 3 panelists who found it to be comfortable to use without skin irritation
  • Toners (Test Examples 1 to 5) having the compositions shown in Table 1 below were prepared by a conventional method. The antiseptic effect on each fungus was evaluated according to the above test and evaluation method.
  • a lotion containing phenoxyethanol which has been conventionally used as a preservative (Test Example 1), has a high antiseptic effect on Pseudomonas aeruginosa (Ps), and Escherichia coli (E) and Candida (Can). And the antiseptic effect on black mold (Asp) was moderate, and the antiseptic effect on Staphylococcus aureus (S) was weak.
  • the lotion containing 4-hydroxyacetophenone, which is an acetophenone derivative (Test Example 2), had a strong antiseptic effect on Ps, E and Asp, a moderate antiseptic effect on Can, and a weak antiseptic effect on S.
  • the lotion (Test Example 3 and Test Example 4) in which glyceryl monocaprate, which is a fatty acid glyceryl ester, and phenoxyethanol are combined is compared with the case of phenoxyethanol alone (Test Example 1), and E, S and While the antiseptic effect on Can was improved, the death rate of Asp was slowed down, and the antiseptic effect on mold was significantly reduced.
  • the combination of fatty acid glyceryl ester with phenoxyethanol counteracts some of the antiseptic effects of phenoxyethanol.
  • the lotion containing the fatty acid glyceryl ester of the present invention in combination with the acetophenone derivative (Test Example 5) showed a sufficient antiseptic effect on all of Ps, E, S, Can and Asp.

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Abstract

The present invention aims to provide a cosmetic that has a high preservative effect against both fungi and bacteria. In addition, the present invention aims to provide a preservative-free cosmetic. This cosmetic is characterized by containing: (A) a C8–12 fatty acid glyceryl ester and (B) a specific acetophenone derivative. The present invention also pertains to a method for improving the preservative power against fungi and bacteria of a cosmetic or other product to be preserved, said method including the blending of component (A) and component (B).

Description

化粧料Cosmetics
　本発明は、高い防腐効果を有する化粧料に関する。 The present invention relates to a cosmetic having a high antiseptic effect.
　化粧料は、開封後長期にわたって使用されるため、微生物の生育や繁殖を抑制するための防腐効果を有することが不可欠である。そのため、化粧料には、メチルパラベン、エチルパラベンなどのパラベン類やフェノキシエタノールといった防腐剤が配合されるのが一般的である。しかしながら、近年の安全性志向の高まりから、化粧料においても無添加化粧料が好まれる傾向があり、添加物の一つとして防腐剤を配合していない化粧料が求められている。そこで、従来の化粧料用防腐剤に替えて、化粧料に防腐効果を付与する技術が開発されている。 Since cosmetics are used for a long time after opening, it is indispensable to have an antiseptic effect to suppress the growth and reproduction of microorganisms. Therefore, it is common for cosmetics to contain parabens such as methylparaben and ethylparaben and preservatives such as phenoxyethanol. However, due to the growing safety consciousness in recent years, additive-free cosmetics tend to be preferred as cosmetics, and cosmetics containing no preservatives are required as one of the additives. Therefore, a technique for imparting an antiseptic effect to cosmetics has been developed in place of the conventional preservatives for cosmetics.
　中鎖脂肪酸グリセリンエステルやショ糖脂肪酸エステルは、安全性が高く、静菌作用を有する物質として提案されている。しかし、高い静菌作用を得ようとして多く配合すると皮膚への刺激が生じることがある。また、酵母やバクテリアに対して静菌作用を示す反面、カビ類に対しては静菌作用が弱く、化粧料に広い抗菌スペクトルを提供することは困難であった。 Medium-chain fatty acid glycerin ester and sucrose fatty acid ester have been proposed as highly safe and bacteriostatic substances. However, if a large amount is added in order to obtain a high bacteriostatic effect, irritation to the skin may occur. In addition, while it has a bacteriostatic effect on yeast and bacteria, it has a weak bacteriostatic effect on molds, and it has been difficult to provide a broad antibacterial spectrum for cosmetics.
　特許文献１では、（Ａ）０．２質量％以上の２，２－ビス（ヒドロキシメチル）プロピオン酸ｎ－ヘキシルと、（Ｂ）炭素数３～９の多価アルコール、炭素数６～８のアルキルグリセリルエーテルおよび炭素数８～１２の脂肪酸グリセリルエステルから選択される１種又は２種以上とを特定比率で組み合わせることによって、防腐抗菌効果を有する皮膚外用剤が得られることが記載されている。 In Patent Document 1, (A) 0.2% by mass or more of n-hexyl 2,2-bis (hydroxymethyl) propionic acid, (B) a polyhydric alcohol having 3 to 9 carbon atoms, and 6 to 8 carbon atoms. It is described that a skin external preparation having an antiseptic and antibacterial effect can be obtained by combining one or more selected from alkyl glyceryl ether and fatty acid glyceryl ester having 8 to 12 carbon atoms in a specific ratio.
　また、ジプロピレングリコール、１，３－ブチレングリコール等の２価グリコールは、安全性が高い保湿剤であり、広く化粧料に配合されるが、抗菌作用も有することが知られている。しかし、このような２価グリコールで高い抗菌効果を得ようとすると化粧料中に高配合する必要があり、化粧料にべたつきが生じる場合があった。 In addition, divalent glycols such as dipropylene glycol and 1,3-butylene glycol are highly safe moisturizers and are widely blended in cosmetics, but are known to have antibacterial activity. However, in order to obtain a high antibacterial effect with such divalent glycol, it is necessary to add a large amount to the cosmetic, and the cosmetic may become sticky.
　よって、化粧料に防腐作用を付与する物質としては、化粧料の使用性を損なうことなく、広い抗菌スペクトルが実現できるものが必要である。 Therefore, as a substance that imparts an antiseptic effect to cosmetics, a substance that can realize a wide antibacterial spectrum without impairing the usability of the cosmetics is required.
特開２０１１－４６７４７号公報Japanese Unexamined Patent Publication No. 2011-46747
　本発明は、真菌類および細菌類に対して高い防腐効果を有する化粧料を提供することを目的とする。 An object of the present invention is to provide a cosmetic having a high antiseptic effect against fungi and bacteria.
　発明者等は、前記の課題を解決すべく鋭意検討を重ねた結果、ある種の脂肪酸グリセリルエステルと特定のアセトフェノン誘導体とを組み合わせた場合に、真菌類および細菌類の両方に対して高い防腐作用を発揮することを見出し、本発明を完成するに至った。 As a result of diligent studies to solve the above problems, the inventors have a high antiseptic effect on both fungi and bacteria when a certain fatty acid glyceryl ester and a specific acetophenone derivative are combined. The present invention has been completed.
　すなわち、本発明は、
（Ａ）炭素数８～１２の脂肪酸グリセリルエステル、および
（Ｂ）以下の式（１）で表されるアセトフェノン誘導体 That is, the present invention
(A) Fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) Acetophenone derivative represented by the following formula (1).
Figure JPOXMLDOC01-appb-C000004
Figure JPOXMLDOC01-appb-C000004
（式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表す）
を含有してなる化粧料を提供する。 (In the formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group)
To provide a cosmetic containing.
　本発明の化粧料は、上記構成とすることにより、真菌類および細菌類に対して高い防腐効果を有する化粧料を得ることができる。前記（Ａ）成分と（Ｂ）成分により十分な防腐効果を得ることができるので、防腐効果を得るために２価グリコールや低級アルコールを高配合する必要がなく、べたつきや肌への刺激性のない、使用感の良好な化粧料を得ることができる。また、通常化粧料に用いられる防腐剤を含まない、すなわち「防腐剤フリー」の化粧料を実現することができる。 By adopting the above-mentioned composition, the cosmetic of the present invention can obtain a cosmetic having a high antiseptic effect against fungi and bacteria. Since a sufficient antiseptic effect can be obtained from the components (A) and (B), it is not necessary to add a high amount of divalent glycol or lower alcohol in order to obtain the antiseptic effect, and it is sticky and irritating to the skin. It is possible to obtain a cosmetic having a good feeling of use. In addition, preservative-free cosmetics that do not contain preservatives that are usually used in cosmetics can be realized.
　本発明の化粧料は、（Ａ）炭素数８～１２の脂肪酸グリセリルエステルと、（Ｂ）特定のアセトフェノン誘導体とを含むことを特徴とする。前記（Ａ）成分および（Ｂ）成分の配合により、化粧料に防腐効果が付与される。以下、本発明の化粧料を構成する各成分について詳述する。 The cosmetic of the present invention is characterized by containing (A) a fatty acid glyceryl ester having 8 to 12 carbon atoms and (B) a specific acetophenone derivative. The combination of the component (A) and the component (B) imparts an antiseptic effect to the cosmetic. Hereinafter, each component constituting the cosmetic of the present invention will be described in detail.
＜（Ａ）脂肪酸グリセリルエステル＞
　本発明の化粧料に配合される（Ａ）脂肪酸グリセリルエステル（以下、単に「（Ａ）成分」と称する場合がある）は、化粧料に通常配合される脂肪酸グリセリルエステルであって、炭素数が８～１２のものである。例としては、カプリル酸グリセリル、２－エチルヘキサン酸グリセリル、カプリン酸グリセリル、ウンデシレン酸グリセリル、ラウリン酸グリセリル等が挙げられる。本発明の化粧料においては、（Ａ）成分として上記の脂肪酸グリセリルエステルの１種又は２種以上を組み合わせて用いてもよい。本発明においては、カプリン酸グリセリルを用いるのが好ましく、モノカプリン酸グリセリルを用いるのがさらに好ましい。 <(A) Fatty acid glyceryl ester>
The (A) fatty acid glyceryl ester (hereinafter, may be simply referred to as “component (A)”) blended in the cosmetic of the present invention is a fatty acid glyceryl ester usually blended in cosmetics and has a carbon number of carbon. It is from 8 to 12. Examples include glyceryl caprylate, glyceryl 2-ethylhexanoate, glyceryl caproate, glyceryl undecylenate, glyceryl laurate and the like. In the cosmetic of the present invention, one or more of the above fatty acid glyceryl esters may be used as the component (A). In the present invention, it is preferable to use glyceryl caprate, and it is more preferable to use glyceryl monocaprate.
　（Ａ）成分の配合量は、化粧料全量に対して、下限値が０．０１質量％以上又は０．０５質量％以上であることが好ましく、上限値が０．４質量％以下又は０．３質量％以下であることが好ましい。よって、好ましい配合量範囲として０．０１～０．４質量％、０．０１～０．３質量％、０．０５～０．４質量％、０．０５～０．３質量％等が挙げられる。配合量が０．０１質量％未満であると十分な防腐・抗菌作用が得られない場合があり、配合量が０．４質量％を超えると肌に刺激を感じる場合がある。 The lower limit of the amount of the component (A) is preferably 0.01% by mass or more or 0.05% by mass or more, and the upper limit is 0.4% by mass or less or 0. It is preferably 3% by mass or less. Therefore, preferred compounding amount ranges include 0.01 to 0.4% by mass, 0.01 to 0.3% by mass, 0.05 to 0.4% by mass, 0.05 to 0.3% by mass, and the like. .. If the blending amount is less than 0.01% by mass, sufficient antiseptic / antibacterial action may not be obtained, and if the blending amount exceeds 0.4% by mass, the skin may be irritated.
＜（Ｂ）アセトフェノン誘導体＞
　本発明の化粧料に配合される（Ｂ）アセトフェノン誘導体（以下、単に「（Ｂ）成分」と称する場合がある）は、化粧料に通常配合されるアセトフェノン誘導体であって、以下の式（１）で表される化合物またはその塩である。 <(B) Acetophenone derivative>
The (B) acetophenone derivative (hereinafter, may be simply referred to as “component (B)”) blended in the cosmetic of the present invention is an acetophenone derivative usually blended in cosmetics and has the following formula (1). ) Or a salt thereof.
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
　上記式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表し、Ｒ１およびＲ２がアセチル基に対して、オルト、メタまたはパラ位に配置する。 In the above formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group, and R 1 and R 2 are arranged at the ortho, meta or para position with respect to the acetyl group.
　本発明においては、以下に挙げる化合物からなる群から選択される１種または２種以上であることが好ましい。 In the present invention, it is preferable that the compound is one or more selected from the group consisting of the following compounds.
アセトフェノン Acetophenone
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
２－ヒドロキシアセトフェノン 2-Hydroxyacetophenone
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
３－ヒドロキシアセトフェノン 3-Hydroxyacetophenone
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
４－ヒドロキシアセトフェノン 4-Hydroxyacetophenone
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　なかでも、本発明においては、４－ヒドロキシアセトフェノンがさらに好ましい。 Among them, 4-hydroxyacetophenone is more preferable in the present invention.
　上記式（１）で表される化合物の塩としては、化粧品として許容可能な塩または薬学的に許容可能な塩であればよく、例としてナトリウム塩、カリウム塩、アンモニウム塩等が挙げられる。 The salt of the compound represented by the above formula (1) may be a cosmetically acceptable salt or a pharmaceutically acceptable salt, and examples thereof include sodium salt, potassium salt, ammonium salt and the like.
　（Ｂ）成分の配合量は、化粧料全量に対して、下限値が０．０６質量％以上又は０．１質量％以上であることが好ましく、上限値が２．０質量％以下又は１．０質量％以下であることが好ましい。よって、好ましい配合量範囲として０．０６～２．０質量％、０．０６～１．０質量％、０．１～２．０質量％、０．１～１．０質量％等が挙げられる。配合量が０．０６質量％未満であると十分な防腐・抗菌作用が得られない場合があり、配合量が２．０質量％を超えると肌に刺激を感じる場合がある。 The lower limit of the amount of the component (B) is preferably 0.06% by mass or more or 0.1% by mass or more, and the upper limit is 2.0% by mass or less or 1. It is preferably 0% by mass or less. Therefore, preferred compounding amount ranges include 0.06 to 2.0% by mass, 0.06 to 1.0% by mass, 0.1 to 2.0% by mass, 0.1 to 1.0% by mass, and the like. .. If the blending amount is less than 0.06% by mass, sufficient antiseptic / antibacterial action may not be obtained, and if the blending amount exceeds 2.0% by mass, the skin may be irritated.
　本明細書において、「抗菌」とは、対象物の表面上における菌の増殖を抑制することを意味し、「防腐」とは、微生物の侵入、生育、増殖を抑制し、腐敗や発酵が起こらないようにすることを意味する。よって、本発明における「防腐効果」あるいは「防腐作用」とは、「抗菌」および「防腐」の両方を含む効果を指し、対象物が化粧料の場合には、化粧料における細菌類、酵母およびカビ等の真菌類の増殖を抑制して、菌による化粧料の変質を防ぎ、化粧料の保存性を高める効果を意味する。 As used herein, "antibacterial" means suppressing the growth of bacteria on the surface of an object, and "antiseptic" means suppressing the invasion, growth and growth of microorganisms, causing putrefaction and fermentation. Means not to. Therefore, the "antiseptic effect" or "antiseptic effect" in the present invention refers to an effect including both "antibacterial" and "antiseptic", and when the object is a cosmetic, fungi, yeast and the like in the cosmetic. It means the effect of suppressing the growth of fungi such as molds, preventing the deterioration of cosmetics by bacteria, and improving the storage stability of cosmetics.
　本発明の研究過程においては、脂肪酸グリセリルエステルは酵母やバクテリアに対する防腐作用が強く、カビに対しては防腐作用が弱い性質があること、アセトフェノン誘導体はカビに対する防腐作用が強く、酵母やバクテリアに対しては防腐作用が弱いという性質が明らかとなった。一方、防腐剤として化粧料に通常用いられるフェノキシエタノールは緑膿菌に対する防腐作用が強いがその他のバクテリアや酵母・カビに対しては防腐作用が劣っていた。そこで、フェノキシエタノールと脂肪酸グリセリルエステルとを組み合わせると、多くの微生物に対して防腐作用が向上したが、カビの死滅速度が著しく遅くなるという両者単独の場合に有していた防腐効果の一部が打ち消されることが明らかとなった。 In the research process of the present invention, the fatty acid glyceryl ester has a strong antiseptic effect on yeast and bacteria and has a weak antiseptic effect on mold, and the acetophenone derivative has a strong antiseptic effect on mold and against yeast and bacteria. It became clear that the antiseptic effect was weak. On the other hand, phenoxyethanol, which is usually used as an antiseptic in cosmetics, has a strong antiseptic effect on Pseudomonas aeruginosa, but is inferior in antiseptic effect on other bacteria, yeast and mold. Therefore, when phenoxyethanol and fatty acid glyceryl ester were combined, the antiseptic effect on many microorganisms was improved, but some of the antiseptic effects that had been possessed in the case of both alone, that the mold killing rate was significantly slowed down, were canceled. It became clear that
　本発明においては、脂肪酸グリセリルエステルとアセトフェノン誘導体とを組み合わせることによって、互いの利点を打ち消すことなく、カビ、酵母およびバクテリアのすべてに対して高い防腐効果が得られ、広い抗菌スペクトルをもつ新規の組み合わせを実現することができた。 In the present invention, the combination of a fatty acid glyceryl ester and an acetophenone derivative provides a high antiseptic effect against all of molds, yeasts and bacteria without canceling each other's advantages, and is a novel combination having a broad antibacterial spectrum. Was able to be realized.
　本発明に係る脂肪酸グリセリルエステルは、特許文献１において、２，２－ビス（ヒドロキシメチル）プロピオン酸ｎ－ヘキシルとの組み合わせによって防腐抗菌効果を示すことが記載されている。また、本発明に係るアセトフェノン誘導体は、特許文献２（特開２０１８－９０５７９）において、アシルプロリン（例としてデカノイルプロリン）、アシルグリシン（例としてオクタノイルグリシン、ウンデシレノイルグリシン）等のアシルアミノ酸と多価アルコールとの組み合わせによって、細菌や真菌に対して防腐効果を示すことが記載されている。 Patent Document 1 describes that the fatty acid glyceryl ester according to the present invention exhibits an antiseptic and antibacterial effect in combination with n-hexyl 2,2-bis (hydroxymethyl) propionic acid. Further, the acetphenone derivative according to the present invention is an acyl amino acid such as acylproline (eg, decanoylproline) and acylglycine (eg, octanoylglycine, undecilenoylglycine) in Patent Document 2 (Japanese Patent Laid-Open No. 2018-90579). It is described that the combination of and polyhydric alcohol has an antiseptic effect on bacteria and fungi.
　一方、本発明においては、（Ａ）脂肪酸グリセリルエステルと（Ｂ）特定のアセトフェノン誘導体とを組み合わせることによって防腐効果が発揮されるので、特許文献１および２に記載される２，２－ビス（ヒドロキシメチル）プロピオン酸ｎ－ヘキシルや、アシルプロリン（例としてデカノイルプロリン）およびアシルグリシン（例としてオクタノイルグリシン、ウンデシレノイルグリシン）等のアシルアミノ酸を配合しなくともよい。よって、本発明の態様には、２，２－ビス（ヒドロキシメチル）プロピオン酸ｎ－ヘキシルおよび／またはアシルアミノ酸を含まない態様が包含される。 On the other hand, in the present invention, since the antiseptic effect is exhibited by combining (A) a fatty acid glyceryl ester and (B) a specific acetphenone derivative, 2,2-bis (hydroxyl) described in Patent Documents 1 and 2 is exhibited. It is not necessary to add n-hexyl propionate (methyl) and acyl amino acids such as acylproline (eg, decanoylproline) and acylglycine (eg, octanoylglycine, undecilenoylglycine). Thus, aspects of the invention include aspects that do not contain n-hexyl 2,2-bis (hydroxymethyl) propionate and / or acyl amino acids.
　本発明の化粧料は、通常化粧料として配合される種種の成分を配合してよい。例として、通常化粧料に用いられる炭化水素油、高級脂肪酸、高級アルコール、合成エステル油、シリコーン油、液体油脂、固体油脂、ロウ等の油分、紫外線防御剤、油相増粘剤、界面活性剤、水、低級アルコール、多価アルコール、水溶性高分子、保湿剤、粉末、色材、香料、中和剤、キレート剤、ｐＨ調整剤、ビタミン類、酸化防止剤、薬剤等を適宜必要に応じて含む。 The cosmetic of the present invention may contain various components that are usually blended as cosmetics. For example, hydrocarbon oils, higher fatty acids, higher alcohols, synthetic ester oils, silicone oils, liquid fats and oils, solid fats and oils, oils such as wax, UV protective agents, oil phase thickeners, and surfactants that are usually used in cosmetics. , Water, lower alcohol, polyhydric alcohol, water-soluble polymer, moisturizer, powder, coloring material, fragrance, neutralizer, chelating agent, pH adjuster, vitamins, antioxidants, chemicals, etc. as needed Including.
　本発明においては、前記（Ａ）脂肪酸グリセリルエステルと前記（Ｂ）アセトフェノン誘導体により、十分な防腐効果が得られるので、防腐剤として化粧料に通常用いられるフェノキシエタノールおよびパラベン類を配合しなくともよい。したがって、本発明の態様には、フェノキシエタノールおよび／またはパラベン類を含まない態様が包含される。本発明によれば、防腐剤を含まない化粧料、すなわち「防腐剤フリー」の化粧料を実現することができる。 In the present invention, the (A) fatty acid glyceryl ester and the (B) acetophenone derivative provide a sufficient antiseptic effect, so that it is not necessary to add phenoxyethanol and parabens, which are usually used in cosmetics, as preservatives. Therefore, aspects of the present invention include aspects that do not contain phenoxyethanol and / or parabens. According to the present invention, a preservative-free cosmetic, that is, a "preservative-free" cosmetic can be realized.
　従来から、化粧料に防腐効果を付与するために、ジプロピレングリコール、１，３－ブチレングリコール等の２価グリコールを化粧料全量に対して１０質量％を超えて配合される場合がある。本発明によれば、前記（Ａ）脂肪酸グリセリルエステルと前記（Ｂ）アセトフェノン誘導体により十分な防腐効果が得られるので、２価グリコールの配合量を１０質量％以下にすることが可能となる。よって、本発明の態様には、２価グリコールの配合量が１０質量％以下である態様が包含される。２価グリコールの配合量を少なくすることにより、べたつきのない使用感を有する化粧料を得ることができる。 Conventionally, in order to impart an antiseptic effect to cosmetics, divalent glycols such as dipropylene glycol and 1,3-butylene glycol may be blended in an amount of more than 10% by mass based on the total amount of cosmetics. According to the present invention, since a sufficient antiseptic effect can be obtained by the (A) fatty acid glyceryl ester and the (B) acetophenone derivative, the blending amount of the divalent glycol can be reduced to 10% by mass or less. Therefore, the aspect of the present invention includes an aspect in which the blending amount of the divalent glycol is 10% by mass or less. By reducing the amount of divalent glycol blended, it is possible to obtain a cosmetic having a non-sticky feel.
　また、従来から、エタノール等の低級アルコールの配合量を増やして抗菌効果を得る場合もある。本発明によれば、前記（Ａ）脂肪酸グリセリルエステルと前記（Ｂ）アセトフェノン誘導体により十分な防腐効果が得られるので、低級アルコールの配合量を３質量％以下とすることができる。よって、本発明の態様には、エタノール等の低級アルコールの配合量が１０質量％以下又は３質量％以下である態様、および低級アルコールを配合しない態様が包含される。低級アルコールの配合量を少なくすることにより、肌への刺激が十分に抑制された化粧料を得ることができる。 In addition, conventionally, the amount of lower alcohol such as ethanol may be increased to obtain an antibacterial effect. According to the present invention, since a sufficient antiseptic effect can be obtained by the (A) fatty acid glyceryl ester and the (B) acetophenone derivative, the blending amount of the lower alcohol can be set to 3% by mass or less. Therefore, the aspect of the present invention includes an aspect in which the blending amount of the lower alcohol such as ethanol is 10% by mass or less or 3% by mass or less, and a mode in which the lower alcohol is not blended. By reducing the amount of the lower alcohol blended, it is possible to obtain a cosmetic product in which irritation to the skin is sufficiently suppressed.
　本発明に係る（Ａ）脂肪酸グリセリルエステルと（Ｂ）特定のアセトフェノン誘導体とを対象物に配合すると、配合した対象物は、細菌類、酵母、カビ等の真菌類に対して優れた防腐力を示す。このため、本発明によれば、防腐対象物に、本発明に係る（Ａ）成分および（Ｂ）成分を配合することにより、該防腐対象物の細菌類および真菌類に対する防腐力を高めることができる。ここで、防腐対象物は化粧料に限定されず、軟膏等の皮膚外用剤、香水、コロン等のフレグランス製品、汗拭きシート等の生活衛生用品、おしり拭き等の乳児用衛生用品等が例示される。 When (A) fatty acid glyceryl ester and (B) specific acetophenone derivative according to the present invention are blended in an object, the blended object has excellent antiseptic activity against fungi such as bacteria, yeast and mold. show. Therefore, according to the present invention, by blending the components (A) and (B) according to the present invention with the antiseptic object, the antiseptic power of the antiseptic object against bacteria and fungi can be enhanced. can. Here, the antiseptic object is not limited to cosmetics, and examples thereof include skin external preparations such as ointments, fragrance products such as perfumes and colons, daily hygiene products such as sweat wipes, and baby hygiene products such as wipes. NS.
　すなわち、本発明は、（Ａ）炭素数８～１２の脂肪酸グリセリルエステル、および
（Ｂ）以下の式（１）で表されるアセトフェノン誘導体 That is, the present invention comprises (A) a fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) an acetophenone derivative represented by the following formula (1).
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
（式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表す）
を、防腐対象物に配合することを含む、真菌類および細菌類に対する防腐力を高める方法に関する。本発明においては、防腐対象物が化粧料であることが好ましい。 (In the formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group)
The present invention relates to a method for enhancing the antiseptic activity against fungi and bacteria, including the addition of the above into an antiseptic object. In the present invention, it is preferable that the preservative object is a cosmetic.
　前記方法においては、本発明に係る（Ａ）成分および（Ｂ）成分は、防腐対象物の完成品に添加されてもよいし、防腐対象物の製造工程の際に配合されてもよい。（Ａ）成分および（Ｂ）成分は、同時に配合されてもよいし、別々に配合されてもよい。別々に配合する場合には、（Ａ）成分および（Ｂ）成分のいずれが先でもよい。 In the above method, the components (A) and (B) according to the present invention may be added to the finished product of the antiseptic object, or may be blended during the manufacturing process of the antiseptic object. The component (A) and the component (B) may be blended at the same time or separately. When blended separately, either component (A) or component (B) may come first.
　本発明に係る化粧料の剤形としては、特に限定されず、通常の化粧料の剤形であればいずれのものも利用できる。すなわち、液状、ゲル状、ペースト状、乳液状、クリーム状、噴霧状等のものが利用できる。 The dosage form of the cosmetic according to the present invention is not particularly limited, and any dosage form of ordinary cosmetics can be used. That is, liquid, gel, paste, milky, cream, spray and the like can be used.
　本発明に係る化粧料としては、特に限定されず、化粧水、保湿クリーム等のスキンケア化粧料、ファンデーション、ＢＢクリーム、アイシャドウ、口紅等のメイクアップ化粧料、日焼け止め化粧料、パック剤等に配合することができる。 The cosmetics according to the present invention are not particularly limited, and include skin care cosmetics such as lotions and moisturizing creams, makeup cosmetics such as foundations, BB creams, eye shadows, and lipsticks, sunscreen cosmetics, and packs. Can be blended.
　また、本発明は、前記（Ａ）脂肪酸グリセリルエステルと前記（Ｂ）アセトフェノン誘導体との組み合わせにより真菌類および細菌類に対する防腐効果を奏するので、本発明によれば、真菌類および細菌類を含む幅広い抗菌スペクトルを有する防腐組成物を得ることができる。すなわち、本発明は、（Ａ）炭素数８～１２の脂肪酸グリセリルエステル、および（Ｂ）以下の式（１）で表されるアセトフェノン誘導体 Further, since the present invention exerts an antiseptic effect on fungi and bacteria by the combination of the (A) fatty acid glyceryl ester and the (B) acetphenone derivative, a wide range including fungi and bacteria is described in the present invention. An antiseptic composition having an antibacterial spectrum can be obtained. That is, the present invention comprises (A) a fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) an acetophenone derivative represented by the following formula (1).
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
（式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表す）
からなる防腐剤組成物に関する。 (In the formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group)
Containing a preservative composition comprising.
　以下に実施例を挙げて本発明をさらに詳述するが、本発明はこれらにより何ら限定されるものではない。配合量は特記しない限り、その成分が配合される系に対する質量％で示す。各実施例について具体的に説明する前に、採用した試験方法および評価方法について説明する。 The present invention will be described in more detail with reference to examples below, but the present invention is not limited thereto. Unless otherwise specified, the blending amount is shown in mass% with respect to the system in which the component is blended. Before concretely explaining each embodiment, the adopted test method and evaluation method will be described.
　常法により、表１に示す組成を有する試験例１～５の化粧水を調製し、防腐効果試験および使用試験を実施した。 The lotions of Test Examples 1 to 5 having the compositions shown in Table 1 were prepared by a conventional method, and an antiseptic effect test and a use test were carried out.
＜防腐効果試験＞
１．試験対象の菌類
Ｐｓ：緑膿菌（菌株名：Ｐｓｅｕｄｏｍｏｎａｓ　ａｅｒｕｇｉｎｏｓａ、ＡＴＣＣ１５４４２）
Ｅ：大腸菌（菌株名：Ｅｓｃｈｅｒｉｃｈｉａ　ｃｏｌｉ、ＡＴＣＣ８７３９）
Ｓ：黄色ブドウ球菌（菌株名：Ｓｔａｐｈｙｌｏｃｏｃｃｕｓ　ａｕｒｅｕｓ、ＡＴＣＣ６５３８）
Ｃａｎ：カンジダ菌（酵母）標準株（菌株名：Ｃａｎｄｉｄａ　ａｌｂｉｃａｎｓ、ＡＴＣＣ１０２３１）
Ａｓｐ：黒カビ（菌株名：Ａｓｐｅｒｇｉｌｌｕｓ　ｂｒａｓｉｌｉｅｎｓｉｓ、ＡＴＣＣ１６４０４） <Preservative effect test>
1. 1. Fungi to be tested Ps: Pseudomonas aeruginosa (strain name: Pseudomonas aeruginosa, ATCC15442)
E: Escherichia coli (strain name: Escherichia coli, ATCC8739)
S: Staphylococcus aureus (strain name: Staphylococcus aureus, ATCC6538)
Can: Candida albicans (yeast) standard strain (strain name: Candida albicans, ATCC10231)
Asp: Black mold (strain name: Aspergillus brasiliensis, ATCC16404)
２．試験
　防腐力評価方法試験はＩＳＯ１１９３０に準じた方法で実施し、以下の式により得られた対数減少値（ＬＲＶ：Ｌｏｇ　Ｒｅｄｕｃｔｉｏｎ　Ｖａｌｕｅ）から細菌類および真菌類に対する防腐力を評価した。
　　ＬＲＶ＝ｌｏｇ１０（０日目の生菌濃度／サンプリング時の生菌濃度） 2. Test Antiseptic power evaluation method The test was carried out by a method according to ISO11930, and the antiseptic power against bacteria and fungi was evaluated from the logarithmic reduction value (LRV: Log Reduction Value) obtained by the following formula.
LRV = log10 (live cell concentration on day 0 / live cell concentration at sampling)
３．評価
　下記基準に従って防腐効果を評価し、Ａ判定であったもののみを十分な防腐力と判断した。
Ｐｓ、Ｅ、Ｓに対する防腐効果の評価基準
　　Ａ：７日後にＬＲＶが３以上を示した。
　　Ｂ：ＬＲＶが３以上を示すのに８日～１４日間必要であった。
　　Ｃ：１４日以上経過してもＬＲＶが３未満であった。
Ｃａｎに対する防腐効果の評価基準
　　Ａ：７日後にＬＲＶが１以上を示した。
　　Ｂ：ＬＲＶが１以上を示すのに８日～１４日間必要であった。
　　Ｃ：１４日以上経過してもＬＲＶが１未満であった。
Ａｓｐに対する防腐効果の評価基準
　　Ａ：１４日後にＬＲＶが１以上を示した。
　　Ｂ：ＬＲＶが１以上を示すのに１５日～２８日間必要であった。
　　Ｃ：２８日以上経過してもＬＲＶが１未満であった。 3. 3. Evaluation The antiseptic effect was evaluated according to the following criteria, and only those that were judged as A were judged to have sufficient antiseptic power.
Evaluation Criteria for Antiseptic Effect on Ps, E, S A: LRV was 3 or higher after 7 days.
B: It took 8 to 14 days for the LRV to show 3 or higher.
C: The LRV was less than 3 even after 14 days or more.
Evaluation Criteria for Antiseptic Effect on Can A: LRV was 1 or higher after 7 days.
B: It took 8 to 14 days for the LRV to show 1 or higher.
C: The LRV was less than 1 even after 14 days or more.
Evaluation Criteria for Antiseptic Effect on ASP A: LRV was 1 or higher after 14 days.
B: It took 15 to 28 days for the LRV to show 1 or higher.
C: The LRV was less than 1 even after 28 days or more.
＜使用性試験＞
　パネラー１０名に対して１日あたり２回の頻度で１週間使用してもらい、使用感の満足度とともに皮膚刺激の有無を申告させた。使用感の評価は以下の４段階の基準に分類し、また、刺激感を訴えた人数を確認した。
Ａ：皮膚刺激がなく、使用感が良いと認めたパネラーが８名以上
Ｂ：皮膚刺激がなく、使用感が良いと認めたパネラーが５名以上～８名未満
Ｃ：皮膚刺激がなく、使用感が良いと認めたパネラーが３名以上～５名未満
Ｄ：皮膚刺激がなく、使用感が良いと認めたパネラーが３名未満 <Usability test>
Ten panelists were asked to use the drug twice a day for a week, and they were asked to report the satisfaction of the feeling of use and the presence or absence of skin irritation. The evaluation of usability was classified into the following four criteria, and the number of people who complained of irritation was confirmed.
A: 8 or more panelists who have no skin irritation and feel good to use B: 5 or more to less than 8 panelists who have no skin irritation and feel good to use C: No skin irritation and use 3 or more to less than 5 panelists who found it to be comfortable D: Less than 3 panelists who found it to be comfortable to use without skin irritation
　以下の表１に記載の組成を有する、化粧水（試験例１～５）を常法により調製した。上記試験および評価方法に従って、各菌類に対する防腐効果を評価した。 Toners (Test Examples 1 to 5) having the compositions shown in Table 1 below were prepared by a conventional method. The antiseptic effect on each fungus was evaluated according to the above test and evaluation method.
Figure JPOXMLDOC01-appb-T000012
Figure JPOXMLDOC01-appb-T000012
　表１に示されるように、従来から防腐剤として用いられるフェノキシエタノールを配合した化粧水（試験例１）は、緑膿菌（Ｐｓ）に対する防腐効果は高く、大腸菌（Ｅ）、カンジダ菌（Ｃａｎ）および黒カビ（Ａｓｐ）に対する防腐効果は中程度であり、黄色ブドウ球菌（Ｓ）に対する防腐効果は弱かった。アセトフェノン誘導体である４－ヒドロキシアセトフェノンを配合した化粧水（試験例２）は、Ｐｓ、ＥおよびＡｓｐに対する防腐効果は強く、Ｃａｎに対する防腐効果は中程度であり、Ｓに対する防腐効果は弱かった。また、脂肪酸グリセリルエステルであるモノカプリン酸グリセリルとフェノキシエタノールとを組み合わせて配合した化粧水（試験例３、試験例４）は、フェノキシエタノール単独の場合（試験例１）と比較して、Ｅ、ＳおよびＣａｎに対する防腐効果が向上した反面、Ａｓｐの死滅速度が遅くなり、カビに対する防腐効果が著しく低下した。このことから、脂肪酸グリセリルエステルをフェノキシエタノールと組み合わせるとフェノキシエタノールが有する防腐効果の一部が打ち消されることが示唆された。
　一方、本発明の脂肪酸グリセリルエステルとアセトフェノン誘導体とを組み合わせて配合した化粧水（試験例５）は、Ｐｓ、Ｅ、Ｓ、Ｃａｎ、Ａｓｐのすべてに対して十分な防腐効果を示した。 As shown in Table 1, a lotion containing phenoxyethanol, which has been conventionally used as a preservative (Test Example 1), has a high antiseptic effect on Pseudomonas aeruginosa (Ps), and Escherichia coli (E) and Candida (Can). And the antiseptic effect on black mold (Asp) was moderate, and the antiseptic effect on Staphylococcus aureus (S) was weak. The lotion containing 4-hydroxyacetophenone, which is an acetophenone derivative (Test Example 2), had a strong antiseptic effect on Ps, E and Asp, a moderate antiseptic effect on Can, and a weak antiseptic effect on S. Further, the lotion (Test Example 3 and Test Example 4) in which glyceryl monocaprate, which is a fatty acid glyceryl ester, and phenoxyethanol are combined, is compared with the case of phenoxyethanol alone (Test Example 1), and E, S and While the antiseptic effect on Can was improved, the death rate of Asp was slowed down, and the antiseptic effect on mold was significantly reduced. This suggests that the combination of fatty acid glyceryl ester with phenoxyethanol counteracts some of the antiseptic effects of phenoxyethanol.
On the other hand, the lotion containing the fatty acid glyceryl ester of the present invention in combination with the acetophenone derivative (Test Example 5) showed a sufficient antiseptic effect on all of Ps, E, S, Can and Asp.

Claims (7)

  1. （Ａ）炭素数８～１２の脂肪酸グリセリルエステル、および
    （Ｂ）以下の式（１）で表されるアセトフェノン誘導体
    Figure JPOXMLDOC01-appb-C000001
     （式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表す）
    を含有してなる化粧料。     (A) Fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) Acetophenone derivative represented by the following formula (1).
    Figure JPOXMLDOC01-appb-C000001
     (In the formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group)
    Cosmetics containing.
  2. 前記（Ａ）成分がカプリン酸グリセリルである、請求項１に記載の化粧料。 The cosmetic according to claim 1, wherein the component (A) is glyceryl caprate.
  3. 前記（Ｂ）成分が４－ヒドロキシアセトフェノンである、請求項１又は２に記載の化粧料。 The cosmetic according to claim 1 or 2, wherein the component (B) is 4-hydroxyacetophenone.
  4. フェノキシエタノールおよびパラベン類を含まない、請求項１から３のいずれか一項に記載の化粧料。 The cosmetic according to any one of claims 1 to 3, which does not contain phenoxyethanol and parabens.
  5. 前記（Ａ）成分の配合量が、化粧料全量に対して０．４質量％以下である、請求項１から４のいずれか一項に記載の化粧料。 The cosmetic according to any one of claims 1 to 4, wherein the blending amount of the component (A) is 0.4% by mass or less with respect to the total amount of the cosmetic.
  6. （Ａ）炭素数８～１２の脂肪酸グリセリルエステル、および
    （Ｂ）以下の式（Ｉ）で表されるアセトフェノン誘導体
    Figure JPOXMLDOC01-appb-C000002
     （式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表す）
    を、化粧料に配合することを含む、真菌類および細菌類に対する防腐力を高める方法。     (A) Fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) Acetophenone derivative represented by the following formula (I).
    Figure JPOXMLDOC01-appb-C000002
     (In the formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group)
    A method of enhancing antiseptic activity against fungi and bacteria, including the addition of the above into cosmetics.
  7. （Ａ）炭素数８～１２の脂肪酸グリセリルエステル、および
    （Ｂ）以下の式（Ｉ）で表されるアセトフェノン誘導体
    Figure JPOXMLDOC01-appb-C000003
     （式中、Ｒ１およびＲ２はそれぞれ独立して、水素、ヒドロキシ基またはメトキシ基を表す）
    からなる防腐剤組成物。     (A) Fatty acid glyceryl ester having 8 to 12 carbon atoms, and (B) Acetophenone derivative represented by the following formula (I).
    Figure JPOXMLDOC01-appb-C000003
     (In the formula, R 1 and R 2 independently represent hydrogen, hydroxy group or methoxy group)
    Preservative composition consisting of.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000204039A (en) * 1999-01-12 2000-07-25 Pola Chem Ind Inc Cosmetic suitable for sensitive skin
JP2014172908A (en) * 2013-03-08 2014-09-22 Symrise Ag Antimicrobial compositions
JP2016222669A (en) * 2015-06-02 2016-12-28 味の素株式会社 Cosmetic composition

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EP2774604B1 (en) * 2013-03-08 2017-08-30 Symrise AG Cosmetic compositions
JP2015086159A (en) * 2013-10-30 2015-05-07 株式会社コスモステクニカルセンター Antimicrobial and antiseptic composition, and cosmetic and/or external preparation for skin compounding the same
DE102014104258A1 (en) * 2014-03-26 2015-10-01 Beiersdorf Ag Active ingredient combinations of 4-hydroxyacetophenone and one or more glycerol and / or oligoglycerol esters of branched-chain and / or unbranched-chain alkanecarboxylic acids, as well as cosmetic or dermatological preparations containing these active substance combinations
EP2962678A1 (en) * 2014-06-30 2016-01-06 Symrise AG Flavour and fragrance compositions comprising acetophenone derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000204039A (en) * 1999-01-12 2000-07-25 Pola Chem Ind Inc Cosmetic suitable for sensitive skin
JP2014172908A (en) * 2013-03-08 2014-09-22 Symrise Ag Antimicrobial compositions
JP2016222669A (en) * 2015-06-02 2016-12-28 味の素株式会社 Cosmetic composition

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