WO2010119940A1 - 整髪用化粧料 - Google Patents
整髪用化粧料 Download PDFInfo
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- WO2010119940A1 WO2010119940A1 PCT/JP2010/056821 JP2010056821W WO2010119940A1 WO 2010119940 A1 WO2010119940 A1 WO 2010119940A1 JP 2010056821 W JP2010056821 W JP 2010056821W WO 2010119940 A1 WO2010119940 A1 WO 2010119940A1
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- hair
- hair styling
- component
- styling
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- 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
- A61K8/34—Alcohols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/90—Block copolymers
Definitions
- the present invention is a hair styling cosmetic, particularly easy to apply and thickens immediately after application, so it has a good hair styling effect and is well-familiar to the hair, and has no stickiness at the end of hair styling and excellent re-styling properties It relates to hairdressing cosmetics.
- Hairdressing cosmetics are products used to moisturize the hair while preparing the hairstyle or maintaining the set hairstyle.
- a variety of products such as hair foams, hair sprays, gels, hair waxes, pomades, hair creams, etc. are marketed for these hair styling cosmetics according to various usage forms and preferences of consumers.
- liquid hairdressing cosmetics containing a compound in which polyalkylene glycol is added to a polyhydric alcohol are disclosed (Patent Documents 1 and 2).
- gel-like, spray-like and foam-like hairdressing cosmetics containing resins such as vinyl, acrylic and urethane are disclosed (Patent Document 3 and Patent Document 4).
- waxy hairdressing cosmetics prepared by emulsifying solid wax are disclosed (Patent Documents 5 and 6).
- conventional hairdressing cosmetics such as wax are very excellent in hairstyling power and re-styling properties due to their high viscosity, they are not well adapted to hair and difficult to apply uniformly. Also, some hairs had a sticky feeling after hair styling, and the hair was dusty.
- conventional liquid cosmetics such as liquids, gels, and sprays are water-based and do not have high viscosity, so they are well-adapted to the hair and can be applied uniformly throughout. There is a drawback that it is difficult to exert the hair-styling power until the volatile components such as evaporate and dry.
- the present invention has been made in view of the above prior art, and the problem to be solved is that even in an aqueous base that can be applied uniformly, such as liquid, gel, and spray, the hair-styling effect is obtained immediately after application.
- An object of the present invention is to provide a hair styling cosmetic that can be exerted, has no stickiness at the end of hair styling, and has an appropriate setting power and excellent styling.
- the hairdressing cosmetic composition according to the present invention comprises (a) block-type alkylene oxide derivatives ((I), (II), () that are solid at room temperature (25 ° C.), insoluble in water, and transparently soluble in lower alcohols.
- the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group is 20 to 80% by mass, and R 1 and R 2 may be the same or different and may be the same or different.
- a hydrogen group or a hydrogen atom, and R 3 is a linear or branched hydrocarbon group having 1 to 36 carbon atoms.
- the hair is well-familiar and can be applied uniformly.
- the hair-styling cosmetic composition has hair styling power immediately after application, does not become sticky after hair styling, imparts an appropriate setting power to the hair, and at the same time has excellent hair styling properties.
- Block-type alkylene oxide derivative contained in the hairdressing cosmetic composition of the present invention is one or more compounds selected from the following formulas (I), (II), and (III): Yes, it is solid at room temperature (25 ° C.), insoluble in water, and transparently soluble in lower alcohols.
- AO is an oxyalkylene group having 3 to 4 carbon atoms, and specifically includes an oxypropylene group, an oxybutylene group, an oxyisobutylene group, and an oxytrimethylene group. And an oxytetramethylene group. Preferably, an oxypropylene group and an oxybutylene group are mentioned.
- EO is an oxyethylene group.
- the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group is 20 to 80% by mass, preferably 40 to 70% by mass.
- the proportion of the oxyethylene group is less than 20% by mass, it tends to be inferior in smoothness, and when it exceeds 80% by mass, it tends to cause stickiness.
- R 1 and R 2 are a hydrocarbon group having 1 to 4 carbon atoms or a hydrogen atom, and examples of the hydrocarbon group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, Examples thereof include a tert-butyl group.
- a methyl group and an ethyl group are preferred.
- Hydrocarbon groups having 5 or more carbon atoms tend to have poor hydrophilicity and a feeling of moisture.
- R 1 and R 2 may be the same type, or may be a mixture of a hydrocarbon group having 1 to 4 carbon atoms and a hydrogen atom, or a mixture of different hydrocarbon groups having 1 to 4 carbon atoms. Good. More preferably, R 1 and R 2 are the same or different hydrocarbon groups having 1 to 4 carbon atoms.
- R 3 is a linear or branched hydrocarbon group having 1 to 36 carbon atoms.
- alkylene oxide derivative of the present invention examples include POE (14) POP (7) dimethyl ether, POE (10) POP (10) dimethyl ether, POE (6) POP (14) dimethyl ether, POE (15) POP (5 ) Dimethyl ether, POE (25) POP (25) dimethyl ether, POE (7) POP (12) dimethyl ether, POE (22) POP (40) dimethyl ether, POE (35) POP (40) dimethyl ether, POE (50) POP (40) ) Dimethyl ether, POE (55) POP (30) dimethyl ether, POE (30) POP (34) dimethyl ether, POE (25) POP (30) dimethyl ether, POE (27) POP (14) dimethyl ether, POE (55) POP (2) ) Dimethyl ether, POE (36) POP (41) dimethyl ether, POE (7) POP (12) dimethyl ether, POE (14) POB (7) dimethyl ether, POE (10) POP (10) diethyl
- the blending amount of the block-type alkylene oxide derivative in the hairdressing cosmetic composition of the present invention is preferably 1 to 50% by mass, more preferably 2 to 20% by mass. If the blending amount is less than 1% by mass, the effect of blending may not be sufficiently exhibited, and if it exceeds 50% by mass, stickiness may occur.
- the block-type alkylene oxide derivative of the present invention can be produced by a known method. For example, it can be obtained by addition-polymerizing ethylene oxide and an alkylene oxide having 3 to 4 carbon atoms to a compound having a hydroxyl group, and then subjecting an alkyl halide to an ether reaction in the presence of an alkali catalyst.
- the solvent of the hairdressing cosmetic composition of the present invention contains water and a lower alcohol.
- the water used to water the present invention is not particularly limited, and specifically ion-exchanged water, purified water, tap water, and the like.
- the blending amount of water is preferably 60% by mass or less, and particularly preferably 50% by mass or less, based on the total amount of the hairdressing cosmetic. If it is 60% by mass or more, the block-type alkylene oxide derivative may be separated, and the hair styling effect tends to be insufficient.
- Lower alcohol As the lower alcohol used in the present invention, a monovalent aliphatic alcohol having 1 to 4 carbon atoms can be used, and specifically, ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol and the like can be mentioned. Preferably, ethanol is used.
- the blending amount of the lower alcohol is preferably 40% by mass or more, and particularly preferably 50% by mass or more, based on the total amount of the hairdressing cosmetic composition. If it is less than 40% by mass, the block-type alkylene oxide derivative may be separated, and the hair-styling effect tends to be insufficient and may become sticky.
- the specific block type alkylene oxide derivative (a) component is completely dissolved in a solvent containing water and lower alcohol (b) component.
- the component (a) is in a mixed state in a solvent having a changed composition, thereby providing hair styling power superior to that immediately after application.
- the hairdressing cosmetic composition according to the present invention is such that substantially all of the solvent is volatilized after hairdressing, and the hair-styling component (a) block-type alkylene oxide derivative is deposited in a deposited state on the hair. It is possible to maintain the hair style by demonstrating hair styling power and re-styling.
- the amount of water and lower alcohol as component (b) is such that the time for all the solvent to evaporate is within 20 minutes, more preferably within 10 minutes during normal use. It is desirable to adjust the blending ratio. If the time until all the solvent evaporates is too long, it may be difficult to adjust the hair, but there is no particular limitation as it is possible to use a method of adjusting the hair while forcibly drying it with a dryer or the like. It can be adjusted.
- the hairdressing cosmetic composition of the present invention if necessary, moisturizer, surfactant, ultraviolet absorber, fragrance, antioxidant, antiseptic / antifungal agent, extender pigment, coloring pigment, Ingredients usually used in hairdressing cosmetics such as alcohol can be blended. Further, in the present invention, by blending a specific block type alkylene oxide derivative as a hair styling component, it is more familiar to hair than hair styling cosmetics using conventional hair styling components such as waxes and film-forming polymers.
- hairdressing cosmetic composition having an appropriate setting power and re-styling properties, but in a range not impairing the effect of the present invention, It can also be used in combination with conventional hair styling ingredients such as waxes and film-forming polymers.
- the dosage form of the hairdressing cosmetic composition according to the present invention may be any of a solubilizing system, an emulsifying system, a powder dispersion system, an oil-water two-layer system, and an oil-water-powder three-layer system.
- Preferable use modes of the hairdressing cosmetic composition of the present invention include aerosol type hair spray, pump type hair spray, foam aerosol, hair mist, set lotion, hair styling gel, hair liquid and the like.
- the present invention will be described in more detail with reference to examples.
- the present invention is not limited to these examples.
- the blending amount indicates mass%.
- the scoring standards and evaluation methods used in the present invention will be described.
- Evaluation (1) Familiarity About 10 women's specialties regarding familiarity when 0.5g of sample is applied to a bundle of black virgin hair (length 20cm, mass 4g) and fingered. Evaluation was made by a sensory test using a panel. The evaluation criteria are as follows. Scoring criteria 5 points: Familiar 4 points: Familiar 3 points: Normal 2 points: Slightly familiar 1 point: Familiarity
- Evaluation (2) Hair styling power (arrangement power) during application Applying 0.5g of sample to a bundle of black virgin hair (length 20cm, mass 2g), and 10 people who can easily arrange the hair bundle just after it has been stretched and pinched was evaluated by a sensory test by a female specialist panel.
- the evaluation criteria are as follows. Scoring criteria 5 points: 4 points that are easy to arrange 4 points: 3 points that are easy to arrange 3 points: normal 2 points: 1 point that is difficult to arrange 1 point: cannot be arranged
- Evaluation (3) Hair fixing force (setting force) at the end of hair styling Apply 0.2g of sample to black virgin hair (length 10cm, mass 0.5g), use comb to adjust the shape to straighten, dry at room temperature for 20 minutes, 5 pieces per sample A strand was produced. The maximum stress when this strand was pressed 5 mm was measured using a rheometer (RTC-2002DD (manufactured by Rheotech)).
- the evaluation method is as follows. Evaluation method A: Maximum stress value is 200 g weight or more B: Maximum stress value is 150 to less than 200 g weight C: Maximum stress value is less than 100 to 150 g weight D: Maximum stress value is less than 50 to 100 g weight E: Maximum stress value Less than 50g
- Evaluation (4) Re-styling power at the end of hair styling (arrangement power) After the evaluation (2), the ease of arrangement when the hair bundle dried for 20 minutes at room temperature was pinched again and twisted and moved was evaluated by a sensory test by 10 female panelists.
- the evaluation criteria are as follows. Scoring criteria 5 points: 4 points that are easy to arrange 4 points: 3 points that are easy to arrange 3 points: normal 2 points: 1 point that is difficult to arrange 1 point: cannot be arranged
- Evaluation (5) No stickiness at the end of hair styling Evaluation of the stickiness of the hair when performing the evaluation (4) was evaluated by a sensory test by 10 female panelists.
- the evaluation criteria are as follows. Scoring criteria : 5 points: No stickiness at all 4 points: No stickiness at all 3 points: Neither point: 2 points: Somewhat sticky feelings: 1 point: Very sticky
- Evaluation (6) Hair styling power (arrangement power) 2 hours after application After the evaluation (2), the ease of arrangement when the hair bundle left for 2 hours was pinched again and twisted and moved was evaluated by a sensory test by 10 female panelists.
- the evaluation criteria are as follows. Scoring criteria 5 points: 4 points that are easy to arrange 4 points: 3 points that are easy to arrange 3 points: normal 2 points: 1 point that is difficult to arrange 1 point: cannot be arranged
- Evaluation (7) Solubility After the sample was prepared, the solubility was visually observed.
- the evaluation method is as follows. Evaluation method A: Transparent and uniformly dispersed B: White turbidity, but uniformly dispersed C: White turbidity, not uniformly dispersed
- the present inventors prepared samples having the composition shown in Table 1 below, in which various ingredients were blended as hair styling ingredients, and manufactured hair styling cosmetics by conventional methods. And each sample was evaluated by the said evaluation method about the evaluation item (3). Furthermore, the specialized panelists asked each sample to evaluate the evaluation items (1), (2), (4) to (6) according to the above scoring criteria, and the total score was evaluated by the following evaluation method. The results are shown in Table 1. Evaluation method A: Total score is 40 or more B: Total score is 30 or more and less than 40 C: Total score is 20 or more and less than 30 D: Total score is less than 20
- Test Example 1-1 in which an alkylene oxide derivative was blended as a hair styling component, was a hair styling cosmetic with good hair styling and excellent hair styling power when applied. Further, at the end of styling, the solvent in the hair styling cosmetic volatilizes and has an appropriate fixing force (setting force), and is non-sticky and can be restyled even in a hair bundle after 2 hours.
- Test Example 1-2 in which polyvinylpyrrolidone / vinyl acetate copolymer was blended as a hair styling component, the hair was well adapted to hair, but the hair styling power at the time of application was slightly inferior, non-sticky, and re-hair styling. It was inferior in nature.
- Test Example 1-3 in which an acrylic resin alkanolamine was blended as a hair styling component, it was excellent in hair fitting and setting power at the end of hair styling, but was slightly inferior in hair styling power at the time of application and once dried Since the hair became hardened, the hair could not be reshaped and had stickiness.
- Test Example 1-4 in which amphoteric urethane resin was blended as a hair styling component, it was excellent in hair fitting and setting power at the end of hair styling, but was slightly inferior in hair styling power and re-styling properties at the time of application, and also had stickiness Met.
- Test Example 1-5 in which a silylated urethane resin was blended as a hair styling component, the hair was well-familiar and the setting power at the end of hair styling was excellent, but the hair styling power at the time of application was not sufficient and the hair once dried Since the resin hardened, the hair could not be reshaped and had stickiness.
- Test Examples 1-6 in which bead wax is blended as a hair styling component, the hair arrangement ability and re-styling properties are excellent at the time of application, but it is slightly inferior in terms of familiarity with hair, and the hair is set at the end of hair styling. It was inferior in power and very sticky.
- Test Examples 1-7 in which microcrystalline wax was blended as a hair styling component, although the hair arranging power and re-styling properties at the time of application were excellent, stickiness at the end of hair styling was seen, and the hair was familiar and set power It was also inferior.
- the present inventors have studied an alkylene oxide derivative to be blended as a hair styling component.
- the alkylene oxide derivatives of compounds 1 to 12 shown in Table 2 below the solubility at room temperature (25 ° C.) and 60 ° C., the solubility in water and ethanol were confirmed. The case where some undissolved material was observed was evaluated as ⁇ , and the case where it was not dissolved at all was evaluated as ⁇ . The results are shown in Table 2.
- the present inventors prepared samples having the composition described in Tables 3 and 4 below using each of the above alkylene oxide derivatives, and based on the following production method, hairdressing cosmetics (transparent hair cosmetics) Manufactured.
- Hair cosmetic production method Compounds 1 to 12 were heated and melted, dissolved in ethanol, and then ion-exchanged water was added and mixed by stirring to obtain a liquid hair styling agent.
- Evaluation method A Total score is 40 or more B: Total score is 30 or more and less than 40 C: Total score is 20 or more and less than 30 D: Total score is less than 20
- a block type alkylene oxide derivative (one selected from the above formulas (I), (II), and (III)) that is solid at room temperature, insoluble in water and transparently soluble in lower alcohol according to the present invention.
- the hair styling cosmetics of Test Examples 2-1 to 2-8 containing two or more compounds) are well-familiar with the hair, and have a hair styling power at the time of application and a re-hair styling power (arrangement power) at the end of hair styling. Both were excellent.
- Test Example 2-9 which is a block-type alkylene oxide derivative represented by the above formula (I) and is compounded with compound 9 that is liquid at room temperature, is well-suited to hair, but has the hair-styling ability and hair-styling at the time of application. Both of the re-styling power (arrangement power) at the end were inferior. Further, the ratio of the oxyethylene group to the total of the oxyalkylene group having 3 to 4 carbon atoms and the oxyethylene group in the block type alkylene oxide derivative of the above formula (II) is about 87% by mass, and is transparently dissolved in water and lower alcohol.
- Test Example 2-10 formulated with possible compound 10 was well-familiar with hair and was excellent in re-styling power (arrangement power) at the end of hair styling, but was inferior in hair styling power at the time of application .
- Test Example 2-11 which is a solid at room temperature but dissolved in water and insoluble in lower alcohol and having a molecular weight of 4000 glycol (Compound 11), is excellent in re-styling power (arrangement power) at the end of hair styling. However, the familiarity with hair was slightly inferior, and the hair styling ability at the time of application was inferior.
- Test Example 2-12 which was mixed with a random alkylene oxide derivative (compound 12) that was liquid at room temperature and slightly insoluble in water, was well-familiar with hair, but the hair styling power at the time of application and the completion of hair styling It was inferior to the re-styling power (arrangement power) at the time.
- the block-type alkylene oxide derivatives (formulas (I), (II) and (III) above) which are solid at room temperature (25 ° C.), insoluble in water and transparently soluble in lower alcohols 1 or 2 or more compounds selected from the above, and (b) a hairdressing cosmetic composition containing water and a lower alcohol as a solvent is excellent in familiarity with hair and has hairstyling power immediately after application. all right. Further, such a hairdressing cosmetic composition according to the present invention has all the solvent volatilized after the completion of hairdressing, the hairdressing component is deposited on the hair, has an appropriate setting power and re-styling property, and also has no stickiness. Met.
- Test Examples 3-1 and 3-2 which had a small blending amount of ethanol and a large blending amount of water, were inferior in all evaluations.
- the improvement of the hair styling power due to the volatilization could not be realized.
- the solubility of the component (a) was poor, the component (a) became cloudy and was not uniformly dispersed.
- Test Examples 3-3 and 2-3 it becomes possible to disperse uniformly as the blending amount of ethanol increases, and not only the hair styling power at the time of application but also the preferential volatilization of ethanol. Accordingly, a hairdressing cosmetic material with improved hairstyling power was obtained.
- the component (a) is dissolved in the component (b) in the cosmetic composition.
- a specific (a) block-type alkylene oxide derivative is blended as a hairdressing component
- 40% by mass or less of lower alcohol and 60% by mass or less of water may be blended in the total amount of the cosmetic. Is preferred.
- hairdressing cosmetic preparations according to the present invention are given below, but the technical scope of the present invention is not limited thereto. All of the obtained hairdressing cosmetics are well-familiar with the hair and can be applied evenly, and have hair-styling power immediately after application, and all the solvent is volatilized after the hairstyling is finished, and there is no stickiness. Also, it had re-styling properties.
- Aerosol spray (% by mass) (1) Ion-exchanged water The remainder (2) Ethanol 50.0 (3) Compound of Test Example 1 10.0 (4) Acrylic resin alkanolamine 5.0 (Plus size L-9909B (manufactured by Reciprocal Chemical Co., Ltd.)) (5) Diglycerin 0.5 (6) Fragrance 0.1 ⁇ Production method> (3) melted in (2), then (4) and (6) are added, and the mixture stirred until uniform is used as the alcohol part. On the other hand, (5) is added to (1) and alcohol parts are further added and stirred uniformly to obtain a stock solution. The aerosol solution 60% and dimethyl ether 40% were filled into an aerosol can and mixed to obtain an aerosol spray.
- Formulation Example 8 Mist Hair Conditioner (mass%) (1) Ion-exchanged water The remainder (2) Ethanol 50.0 (3) Compound of Test Example 5.0 (4) 1,3-BG 5.0 (5) Fragrance 0.2 (6) Wine extract 0.1 ⁇ Production method> (3) melted in (2) and (5) and (6) were added and uniformly dispersed to obtain an alcohol part. Subsequently, the alcohol part was put into the solution obtained by adding (4) to (1) and transparently dissolving it to obtain a transparent mist-like hairdressing agent.
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Abstract
Description
例えば、多価アルコールにポリアルキレングリコールが付加した化合物を配合したリキッド状の整髪用化粧料が開示されている(特許文献1、特許文献2)。また、ビニル、アクリル、ウレタンなどの樹脂を配合したジェル状、スプレー状、フォーム状の整髪用化粧料が開示されている(特許文献3、特許文献4)。また、固形のロウを乳化して配合したワックス状の整髪用化粧料が開示されている(特許文献5、特許文献6)。
一方、従来のリキッド状、ジェル状、スプレー状等の整髪用化粧料は、水系で粘度も高くないため毛髪へのなじみがよく、全体に均一に塗布可能であるが、塗布後、水やアルコールなどの揮発成分が揮散し乾くまで整髪力を発揮しにくいという欠点があった。
本発明は上記従来技術に鑑み行われたものであり、その解決すべき課題は、リキッド状、ジェル状、スプレー状のような均一に塗布可能な水系基剤においても、塗布直後より整髪効果を発揮でき、整髪終了時にはべたつきがなく適度なセット力と再整髪性に優れた整髪用化粧料を提供することにある。
(b)水および低級アルコールを含む溶媒とを含み、
(a)成分が(b)成分に溶解するものであり、
塗布後低級アルコールの優先的な揮散に伴い、(a)成分が組成の変化した溶媒中で混和状態を経て、実質的に全溶媒が揮散することを特徴とする整髪用化粧料である。
R1O-[(AO)p(EO)q(AO)r]-R2 (I)
R1O-[(EO)p(AO)q(EO)r]-R2 (II)
R1O-[(EO)p(AO)qR3(AO)s(EO)r]-R2 (III)
(式中、AOは炭素数3~4のオキシアルキレン基、EOはオキシエチレン基、p、q、rおよびsは平均付加モル数で、1≦p+r≦90、1≦q+s≦90である。炭素数3~4のオキシアルキレン基とオキシエチレン基の合計に対するオキシエチレン基の割合は20~80質量%である。R1およびR2は同一もしくは異なっていてもよい炭素数1~4の炭化水素基又は水素原子であり、R3は炭素数1~36の直鎖または分岐の炭化水素基である。)
前記整髪用化粧料において、(a)成分の配合量が1~50質量%であることが好適である。
前記整髪用化粧料において、(b)成分の水の配合量が60質量%以下、低級アルコールの配合量が40質量%以上であることが好適である。
本発明の整髪用化粧料に含まれるブロック型アルキレンオキシド誘導体は、下記(I)、(II)、(III)式から選ばれる1種または2種以上の化合物であり、常温(25℃)で固体で、水に不溶で低級アルコールに透明溶解可能なものである。
R1O-[(AO)p(EO)q(AO)r]-R2 (I)
R1O-[(EO)p(AO)q(EO)r]-R2 (II)
R1O-[(EO)p(AO)qR3(AO)s(EO)r]-R2 (III)
p、q、r、sは平均付加モル数で、1≦p+r≦90である。また、1≦q+s≦90である。炭素数3~4のオキシアルキレン基またはオキシエチレン基が0であるとなめらかさが落ち、90を超えると使用時のべたつきが過剰になり、アレンジしづらくなる傾向にある。
また、炭素数3~4のオキシアルキレン基とオキシエチレン基の合計に対するオキシエチレン基の割合は20~80質量%であり、好ましくは40~70質量%である。オキシエチレン基の割合が20質量%未満であると、なめらかさに劣る傾向にあり、80質量%を超えると、べたつきを生じる傾向にある。
R1およびR2はそれぞれ同種のものを用いても、炭素数1~4の炭化水素基と水素原子とが混在しても、異種の炭素数1~4の炭化水素基が混在してもよい。より好ましくは、R1およびR2が同一もしくは異なる炭素数1~4の炭化水素基である。
また、R3は炭素数1~36の直鎖または分岐の炭化水素基である。
なお、上記POE、POP、POBは、それぞれポリオキシエチレン、ポリオキシプロピレン、ポリオキシブチレンの略であり、以下、このように略して記載することがある。
本発明のブロック型アルキレンオキシド誘導体は公知の方法で製造することができる。例えば、水酸基を有している化合物にエチレンオキシドおよび炭素数3~4のアルキレンオキシドを付加重合した後、ハロゲン化アルキルをアルカリ触媒の存在下にエーテル反応させることによって得られる。
本発明の整髪用化粧料の溶媒は、水および低級アルコールを含むものである。
本発明に用いる水としては、特に限定されず、具体的にはイオン交換水、精製水、水道水等が挙げられる。
水の配合量は、整髪用化粧料全量に対し、60質量%以下であることが好適であり、特に50質量%以下であることが好適である。60質量%以上ではブロック型アルキレンオキシド誘導体が分離する場合があり、整髪効果が十分でない傾向にある。
本発明に用いる低級アルコールとしては、炭素数1~4の1価脂肪族アルコールを用いることができ、具体的にはエタノール、プロパノール、イソプロパノール、イソブチルアルコール、t-ブチルアルコール等が挙げられる。好ましくはエタノールが挙げられる。
低級アルコールの配合量は、整髪用化粧料全量に対し、40質量%以上であることが好適であり、50質量%以上配合することが特に好適である。40質量%未満ではブロック型アルキレンオキシド誘導体が分離する場合があり、整髪効果が十分でない傾向にあるとともに、べたつく場合がある。
本発明の整髪用化粧料において、通常の使用時においては全溶媒が揮散する時間が20分以内、より好適には10分以内となるよう(b)成分である水および低級アルコールの配合量や配合比を調整することが望ましい。全溶媒が揮散するまでの時間があまりにも長いと、整髪しにくくなる場合があるが、ドライヤーなどで強制的に乾燥させながら整髪する方法も可能であることから、特に限定されるものではなく適宜調整可能である。
また、本発明においては、整髪成分として特定のブロック型アルキレンオキシド誘導体を配合することで、従来の整髪成分であるワックス、皮膜形成性ポリマー等を使用する整髪用化粧料よりも毛髪へのなじみが良く、塗布時の整髪力がありながらも整髪終了時のべたつきがなく、適度なセット力と再整髪性を有する整髪用化粧料を得ることができるが、本発明の効果を損なわない範囲において、従来の整髪成分であるワックス、皮膜形成性ポリマー等と組み合わせて使用することも可能である。
1束の黒色バージンヘア(長さ20cm、質量4g)に試料を0.5g塗布し、指でなじませていったときのなじみのよさについて、10名の女性専門パネラーによる官能試験にて評価した。評価基準は、以下の通りである。
採点基準
5点:なじみがよい
4点:ややなじみがよい
3点:普通
2点:ややなじみが悪い
1点:なじみが悪い
1束の黒色バージンヘア(長さ20cm、質量2g)に試料を0.5g塗布し、均一にのばした直後の毛束について、つまんでねじって動かしたときのアレンジのしやすさを10名の女性専門パネラーによる官能試験にて評価した。評価基準は、以下の通りである。
採点基準
5点:かなりアレンジしやすい
4点:ややアレンジしやすい
3点:普通
2点:ややアレンジしにくい
1点:アレンジできない
黒色バージンヘア(長さ10cm、質量0.5g)に、試料を0.2g塗布し、くしを使いなじませ、まっすぐになるよう形を整え、室温で20分乾燥させ、1試料あたり5本のストランドを作製した。このストランドを5mm押し当てたときの最大応力をレオメーター(RTC-2002DD(レオテック社製))を用いて測定した。評価方法は以下の通りである。
・評価方法
A:最大応力値が200g重以上
B:最大応力値が150~200g重未満
C:最大応力値が100~150g重未満
D:最大応力値が50~100g重未満
E:最大応力値が50g重未満
評価(2)を行った後、室温で20分乾燥させた毛束について、再びつまんでねじって動かしたときのアレンジのしやすさを10名の女性専門パネラーによる官能試験にて評価した。評価基準は、以下の通りである。
採点基準
5点:かなりアレンジしやすい
4点:ややアレンジしやすい
3点:普通
2点:ややアレンジしにくい
1点:アレンジできない
評価(4)を行った際の毛髪のべたつき感を10名の女性専門パネラーによる官能試験にて評価した。評価基準は、以下の通りである。
採点基準
5点:全くべたつきを感じない
4点:ややべたつきを感じない
3点:どちらともいえない
2点:ややべたつきを感じる
1点:かなりべたつきを感じる
評価(2)を行った後、2時間放置させた毛束において、再びつまんでねじって動かしたときのアレンジのしやすさを10名の女性専門パネラーによる官能試験にて評価した。評価基準は、以下の通りである。
採点基準
5点:かなりアレンジしやすい
4点:ややアレンジしやすい
3点:普通
2点:ややアレンジしにくい
1点:アレンジできない
試料を調整後、溶解性を目視で観察した。評価方法は以下の通りである。
・評価方法
A:透明で、均一に分散している
B:白濁があるが、均一に分散している
C:白濁があり、均一に分散していない
そして、各試料を評価項目(3)について上記評価方法で評価した。さらに、専門パネラーには、各試料を評価項目(1)、(2)、(4)~(6)について上記採点基準にて評価してもらい、採点の合計を下記評価方法にて評価した。結果を表1に示す。
・評価方法
A:合計点が40点以上
B:合計点が30点以上40点未満
C:合計点が20点以上30点未満
D:合計点が20点未満
一方、整髪成分としてポリビニルピロリドン・酢酸ビニル共重合体を配合した試験例1-2では、毛髪へのなじみはよいものであったが、塗布時の整髪力にやや劣り、べたつきのなさ、再整髪性にも劣るものであった。
整髪成分としてアクリル樹脂アルカノールアミンを配合した試験例1-3では、毛髪へのなじみおよび整髪終了時のセット力に優れていたが、塗布時の整髪力にやや劣り、一度乾燥してしまうと樹脂が固まってしまうため再整髪できず、べたつきも有するものであった。
整髪成分として両性ウレタン樹脂を配合した試験例1-4では、毛髪へのなじみおよび整髪終了時のセット力に優れていたが、塗布時の整髪力および再整髪性にやや劣り、べたつきも有するものであった。
整髪成分としてシリル化ウレタン系樹脂を配合した試験例1-5では、毛髪へのなじみおよび整髪終了時のセット力に優れていたが、塗布時の整髪力が十分でなく、一度乾燥してしまうと樹脂が固まってしまうため再整髪できず、べたつきも有するものであった。
整髪成分としてビーズワックスを配合した試験例1-6では、塗布時の毛髪のアレンジ力および再整髪性には優れているものの、毛髪へのなじみの点でやや劣り、整髪終了時の毛髪のセット力にも劣り、非常にべたつきのあるものであった。
整髪成分としてマイクロクリスタリンワックスを配合した試験例1-7では、塗布時の毛髪のアレンジ力および再整髪性には優れているものの、整髪終了時のべたつきが見られ、毛髪へのなじみおよびセット力にも劣るものであった。
はじめに、下記表2に示す化合物1~12のアルキレンオキシド誘導体について、常温(25℃)および60℃での状態、水およびエタノールへの溶解性を確認し、完全に溶解しているものを○、溶解していないものが若干見られたものを△、全く溶解していないものを×と評価した。結果を表2に示す。
化合物1~12を加温融解させた後、エタノールに溶解させ、続いてイオン交換水を加えて撹拌混合し液状整髪剤を得た。
・評価方法
A:合計点が40点以上
B:合計点が30点以上40点未満
C:合計点が20点以上30点未満
D:合計点が20点未満
しかし、上記(I)式で表せるブロック型アルキレンオキシド誘導体であるが、常温において液体である化合物9を配合した試験例2-9は、毛髪へのなじみはよいが、塗布時の整髪力および整髪終了時の再整髪力(アレンジ力)のどちらも劣るものであった。
また、上記(II)式のブロック型アルキレンオキシド誘導体における炭素数3~4のオキシアルキレン基とオキシエチレン基の合計に対するオキシエチレン基の割合が約87質量%であり、水および低級アルコールに透明溶解可能である化合物10を配合した試験例2-10は、毛髪へのなじみはよく、整髪終了時の再整髪力(アレンジ力)に優れていたが、塗布時の整髪力に劣るものであった。
また、常温で固体であるが、水に溶解し低級アルコールに不溶な分子量4000のポリエチレングリコール(化合物11)を配合した試験例2-11は、整髪終了時の再整髪力(アレンジ力)に優れていたが、毛髪へのなじみがやや劣り、塗布時の整髪力に劣るものであった。
また、常温において液体で、水への溶解性もやや劣るランダム型アルキレンオキシド誘導体(化合物12)を配合した試験例2-12は、毛髪へのなじみはよいが、塗布時の整髪力および整髪終了時の再整髪力(アレンジ力)に劣るものであった。
一方、試験例3-3、2-3のように、エタノールの配合量を多くするにしたがって、均一に分散することが可能となり、塗布時の整髪力のみならず、エタノールの優先的な揮散に伴い整髪力の向上する整髪用化粧料が得られた。
また、低級アルコールとしてプロパノールを配合した場合にも、プロパノールの配合量が少なく水の配合量が多い試験例3-4において、プロパノールの優先的な揮散に伴う整髪力の向上が実現できなかった。また(a)成分の溶解性に乏しいため(a)成分が白濁し、均一に分散していなかった。
一方、試験例3-5~3-7のように、プロパノールの配合量を多くするにしたがって、均一に分散することが可能となり、塗布時の整髪力のみならず、プロパノールの優先的な揮散に伴い整髪力の向上する整髪用化粧料が得られた。
(質量%)
(1)イオン交換水 残部
(2)エタノール 50.0
(3)試験例1の化合物 10.0
(4)ソルビトール 3.0
(5)POP(70)デカグリセリルエーテル 3.0
(6)ビニルピロリドン・メタクリル酸ジメチルアミノエチル共重合体ジエチル硫酸塩 3.0
(ガフコート755N(ISP社製))
(7)加水分解コムギタンパク液 0.5
(クロペプタイドW(クローダジャパン株式会社製))
(8)トリメチルグリシン 0.5
(9)ポリエーテル変性シリコーン 0.5
(FZ-2222(東レダウコーニング株式会社製))
(10)香料 適量
<製法>
(1)に(4)(7)(8)を溶解させた水相パーツに、(2)に融解させた(3)(5)(6)(9)(10)を順に入れ透明溶解させたものを添加し、攪拌溶解させることで、透明な外観の霧状整髪剤(ヘアミスト)を得た。
(質量%)
(1)イオン交換水 残部
(2)エタノール 40.0
(3)試験例2の化合物 20.0
(4)トレハロース 0.5
(5)POP(9)ジグリセリル 3.0
(6)メタクリロイルオキシエチルカルボキシベタイン・メタクリル酸アルキル共重合体 3.0
(ユカフォーマーR205(三菱化学株式会社製))
(7)ヒドロキシエチル尿素 0.5
(8)塩化ステアリルトリメチルアンモニウム(25%水溶液) 0.5
(9)ポリエーテル変性シリコーン 0.5
(SS-2802(東レダウコーニング株式会社製))
(10)香料 適量
<製法>
(1)に(4)(7)(8)を溶解させた水相パーツに、(2)に融解させた(3)(5)(6)(9)(10)を順に入れ透明溶解させたものを添加し、攪拌溶解させることで、透明な外観の霧状整髪剤(ヘアミスト)を得た。
(質量%)
(1)イオン交換水 残部
(2)イソプロパノール 40.0
(3)試験例3の化合物 5.0
(4)乳酸 0.02
(5)POP(9)ジグリセリル 3.0
(6)アクリル樹脂アルカノールアミン 3.0
(プラスサイズL-9909B(互応化学工業株式会社製))
(7)ポリエチレングリコール(分子量1500) 0.5
(8)POE(3)・POP(20)オリゴコハク酸エステル 0.5
(エステモール50(日清オイリオ株式会社製))
(9)ジココイルエチルヒドロキシエチルモニウムメトサルフェート
0.1
(DEHYQUART L80(コグニス・ジャパン社製))
(10)香料 適量
<製法>
(1)に融解させた(7)(4)(9)を溶解させた水相パーツに、(2)に融解させた(3)(5)(6)(8)(10)を順に入れ透明溶解させたものを添加し、攪拌溶解させることで、透明な外観の霧状整髪剤(ヘアミスト)を得た。
(質量%)
(1)イオン交換水 残部
(2)エタノール 50.0
(3)試験例4の化合物 20.0
(4)ジグリセリン 5.0
(5)キシリトール 0.5
(6)ヒドロキシプロピルセルロース 1.0
(HPC-H(日本曹達株式会社製))
(7)ビニルピロリドン・メタクリル酸N,N-ジメチルアミノエチル・アクリル酸アルキル・ジアクリル酸トリプロピレングリコール共重合体
0.5
(コスカットGA467(大阪有機化学工業株式会社製))
(8)乳酸 0.3
(9)塩化ステアリルトリメチルアンモニウム(25%) 0.5
(10)ポリエーテル変性シリコーン 0.5
(SH3771(東レダウコーニング株式会社製))
(11)ポリ-γ-グルタミン酸Na 0.1
(ジェルプロテインA-8001(出光テクノファイン株式会社製))
(12)ハッカ油 0.1
<製法>
(2)に融解させた(3)(6)(7)(10)(12)を添加しよく均一分散させたものをアルコールパーツとする。一方、(1)に(4)(5)(8)(9)(11)を順に入れ透明溶解させたものにアルコールパーツを入れ、ホモミキサーを用い均一にすることで透明ジェル状の整髪剤を得た。
(質量%)
(1)イオン交換水 残部
(2)エタノール 50.0
(3)試験例5の化合物 30.0
(4)POE(5)・POP(65)ペンタエリスリトールエステル
2.0
(5)ポリエチレングリコール(分子量6000) 2.0
(6)カルボキシビニルポリマー 0.2
(ハイビスワコー105(和光純薬工業株式会社製))
(7)アクリル酸・アクリル酸アルキル(C10-30)共重合体
0.2
(PEMULEN TR-2(B.F.Goodrich Chemical Company社製))
(8)2-アミノメチルプロパノール 0.3
(9)POE(24)・POP(13)デシルテトラデシルエーテル
0.5
(10)ジラウロイルグルタミン酸リシンNa 0.3
(11)イザヨイバラ果実エキス 0.1
(12)香料 0.1
<製法>
(1)に(6)(7)を入れよく分散させた後、融解した(5)、(10)(11)をいれ水相パーツとする。一方、(2)に融解させた(3)(4)(9)(12)を添加し透明溶解させたものを水相パーツに添加、さらに(8)を入れ、攪拌させることで透明ジェル状の整髪剤を得た。
(質量%)
(1)イオン交換水 残部
(2)エタノール 50.0
(3)試験例6の化合物 10.0
(4)イノシトール 0.4
(5)POE(10)メチルグルコシド 2.0
(グルカムE-10(日本ルーブリゾール株式会社製))
(6)ポリビニルピロリドン・酢酸ビニル共重合体 0.2
(PVP/VA S-630(ISP社製))
(7)ジメチルアクリルアミド・アクリロイルジメチルタウリンNaクロスポリマー(特開2005-132782の合成例4) 1.0
(8)POE(50)オレイルエーテル 0.5
(9)ポリエーテル変性シリコーン 0.3
(FZ-2222(東レダウコーニング株式会社製))
(10)真珠タンパクエキス 0.1
(11)香料 0.1
<製法>
(2)に融解させた(3)(8)、続いて(9)(11)を添加し、さらに(7)を入れ均一になるまで攪拌したものをアルコールパーツとする。一方、(1)に(4)(5)(6)(10)を添加し溶解させたものに、アルコールパーツを加え均一攪拌し透明ジェル状の整髪剤を得た。
(質量%)
(1)イオン交換水 残部
(2)エタノール 50.0
(3)試験例1の化合物 10.0
(4)アクリル樹脂アルカノールアミン 5.0
(プラスサイズL-9909B(互応化学工業株式会社製))
(5)ジグリセリン 0.5
(6)香料 0.1
<製法>
(2)に融解させた(3)、続いて(4)(6)を添加し、均一になるまで攪拌したものをアルコールパーツとする。一方、(1)に(5)を加え、さらにアルコールパーツを加え均一に攪拌したものを原液とする。この原液60%とジメチルエーテル40%をエアゾール缶に充填し混合し、エアゾールスプレーを得た。
(質量%)
(1)イオン交換水 残部
(2)エタノール 50.0
(3)試験例7の化合物 5.0
(4)1,3-BG 5.0
(5)香料 0.2
(6)ワインエキス 0.1
<製法>
(2)に融解させた(3)と、(5)(6)を添加しよく均一分散させたものをアルコールパーツとする。続いて、(1)に(4)を入れ透明溶解させたものにアルコールパーツを入れ、透明ミスト状の整髪剤を得た。
Claims (3)
- (a)常温(25℃)で固体で、水に不溶で低級アルコールに透明溶解可能なブロック型アルキレンオキシド誘導体((I)、(II)、(III)式から選ばれる1種または2種以上の化合物)と、
(b)水および低級アルコールを含む溶媒とを含み、
(a)成分が(b)成分に溶解するものであり、
塗布後低級アルコールの優先的な揮散に伴い、(a)成分が組成の変化した溶媒中で混和状態を経て、実質的に全溶媒が揮散することを特徴とする整髪用化粧料。
(式中、AOは炭素数3~4のオキシアルキレン基、EOはオキシエチレン基、p、q、rおよびsは平均付加モル数で、1≦p+r≦90、1≦q+s≦90である。炭素数3~4のオキシアルキレン基とオキシエチレン基の合計に対するオキシエチレン基の割合は20~80質量%である。R1およびR2は同一もしくは異なっていてもよい炭素数1~4の炭化水素基又は水素原子であり、R3は炭素数1~36の直鎖または分岐の炭化水素基である。) - 請求項1に記載の整髪用化粧料において、(a)成分の配合量が1~50質量%であることを特徴とする整髪用化粧料。
- 請求項1または2に記載の整髪用化粧料において、(b)成分の水の配合量が60質量%以下、低級アルコールの配合量が40質量%以上であることを特徴とする整髪用化粧料。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010522117A JP4728449B2 (ja) | 2009-04-16 | 2010-04-16 | 整髪用化粧料 |
EP10764522A EP2420220A4 (en) | 2009-04-16 | 2010-04-16 | HAIR STYLING COSMETIC |
US13/263,101 US20120027710A1 (en) | 2009-04-16 | 2010-04-16 | Hairstyling Cosmetic |
CN2010800169541A CN102395350B (zh) | 2009-04-16 | 2010-04-16 | 整发用化妆品 |
KR1020117025063A KR101168829B1 (ko) | 2009-04-16 | 2010-04-16 | 정발용 화장료 |
HK12106004.7A HK1165291A1 (en) | 2009-04-16 | 2012-06-19 | Hair styling cosmetic |
Applications Claiming Priority (2)
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JP2009-099939 | 2009-04-16 | ||
JP2009099939 | 2009-04-16 |
Publications (1)
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WO2010119940A1 true WO2010119940A1 (ja) | 2010-10-21 |
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PCT/JP2010/056821 WO2010119940A1 (ja) | 2009-04-16 | 2010-04-16 | 整髪用化粧料 |
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US (1) | US20120027710A1 (ja) |
EP (1) | EP2420220A4 (ja) |
JP (1) | JP4728449B2 (ja) |
KR (1) | KR101168829B1 (ja) |
CN (1) | CN102395350B (ja) |
HK (1) | HK1165291A1 (ja) |
TW (1) | TWI386230B (ja) |
WO (1) | WO2010119940A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014214143A (ja) * | 2013-04-30 | 2014-11-17 | 株式会社 資生堂 | 整髪用化粧料 |
JP2015117227A (ja) * | 2013-11-15 | 2015-06-25 | 花王株式会社 | 毛髪化粧料 |
JP2017052726A (ja) * | 2015-09-10 | 2017-03-16 | 株式会社ダリヤ | 毛髪化粧料 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102012203942A1 (de) * | 2012-03-14 | 2013-09-19 | Beiersdorf Ag | Neue Haarfestigungsmittel mit Sorbitol |
CN104379218B (zh) * | 2012-05-15 | 2017-09-08 | 花王株式会社 | 毛发化妆品组合物 |
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JPH06135823A (ja) | 1992-10-28 | 1994-05-17 | Shiseido Co Ltd | 毛髪化粧料 |
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JP2003012467A (ja) * | 2001-06-28 | 2003-01-15 | Mandom Corp | 頭髪用化粧料 |
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-
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- 2010-04-16 US US13/263,101 patent/US20120027710A1/en not_active Abandoned
- 2010-04-16 EP EP10764522A patent/EP2420220A4/en not_active Withdrawn
- 2010-04-16 WO PCT/JP2010/056821 patent/WO2010119940A1/ja active Application Filing
- 2010-04-16 TW TW099111918A patent/TWI386230B/zh not_active IP Right Cessation
- 2010-04-16 CN CN2010800169541A patent/CN102395350B/zh active Active
- 2010-04-16 KR KR1020117025063A patent/KR101168829B1/ko active IP Right Grant
- 2010-04-16 JP JP2010522117A patent/JP4728449B2/ja active Active
-
2012
- 2012-06-19 HK HK12106004.7A patent/HK1165291A1/xx not_active IP Right Cessation
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JPH06135823A (ja) | 1992-10-28 | 1994-05-17 | Shiseido Co Ltd | 毛髪化粧料 |
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JP2014214143A (ja) * | 2013-04-30 | 2014-11-17 | 株式会社 資生堂 | 整髪用化粧料 |
JP2015117227A (ja) * | 2013-11-15 | 2015-06-25 | 花王株式会社 | 毛髪化粧料 |
JP2017052726A (ja) * | 2015-09-10 | 2017-03-16 | 株式会社ダリヤ | 毛髪化粧料 |
Also Published As
Publication number | Publication date |
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KR101168829B1 (ko) | 2012-07-25 |
EP2420220A4 (en) | 2012-04-25 |
JPWO2010119940A1 (ja) | 2012-10-22 |
CN102395350A (zh) | 2012-03-28 |
TWI386230B (zh) | 2013-02-21 |
KR20110134918A (ko) | 2011-12-15 |
HK1165291A1 (en) | 2012-10-05 |
EP2420220A1 (en) | 2012-02-22 |
CN102395350B (zh) | 2013-05-22 |
US20120027710A1 (en) | 2012-02-02 |
JP4728449B2 (ja) | 2011-07-20 |
TW201043258A (en) | 2010-12-16 |
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