WO2015072435A1 - 毛髪化粧料 - Google Patents
毛髪化粧料 Download PDFInfo
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- WO2015072435A1 WO2015072435A1 PCT/JP2014/079792 JP2014079792W WO2015072435A1 WO 2015072435 A1 WO2015072435 A1 WO 2015072435A1 JP 2014079792 W JP2014079792 W JP 2014079792W WO 2015072435 A1 WO2015072435 A1 WO 2015072435A1
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- hair
- hair cosmetic
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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
- A45—HAND OR TRAVELLING ARTICLES
- A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
- A45D7/00—Processes of waving, straightening or curling hair
- A45D7/04—Processes of waving, straightening or curling hair chemical
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- A—HUMAN NECESSITIES
- A45—HAND OR TRAVELLING ARTICLES
- A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
- A45D7/00—Processes of waving, straightening or curling hair
- A45D7/06—Processes of waving, straightening or curling hair combined chemical and thermal
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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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
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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
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/594—Mixtures of polymers
Definitions
- the present invention relates to a hair cosmetic containing a specific polymer.
- the amount of adhesive polymer and set polymer that forms a strong film is increased in order to increase the hairstyle set holding power, and the hairstyle is fixed by the adhesiveness of the polymer and the strong polymer film. Is common.
- Hairdressing ingredients that contain a lot of adhesive polymer make hairstyle by adhering to each other by the adhesiveness of the polymer and give the hairstyle durability, but on the other hand, stickiness is strongly expressed, making hair feel natural It was often difficult to keep, which was a problem.
- hair styling that gives hair styling properties and sustainability by forming a strong film can prevent stickiness, but maintains a hairstyle with a strong film, so it is stiff and natural. In terms of giving a touch, it is still insufficient. Therefore, in addition to preparing and maintaining the hair in the desired shape, there is a need to keep the hair in a natural and non-sticky feel at the same time.
- the hair styling agent can re-hair in addition to excellent sustainability.
- a strong demand That is, there is a demand for a hair styling material that can hold the hairstyle firmly while having a natural feel, and that can freely restyle the hair.
- Patent Document 1 proposes a hair cosmetic that can be re-haired by using a specific set polymer.
- Patent Document 2 (a) a solid polyalkylene glycol, (b) a liquid alcohol, an alkylene oxide addition polymer of alcohol or carboxylic acid, or a polyalkylene glycol polymer, (c) a film-forming polymer, (d) Hairdressing cosmetics containing sugar alcohol in a specific ratio have been proposed. It is known that this hairdressing cosmetic composition imparts re-styling power and improves setting power.
- Patent Document 3 for example, a technique for providing a hair cosmetic composition that imparts adhesiveness by blending an equivalent amount of polyalkylene glycol with a specific hair set polymer, and is excellent in setability and re-styling properties. Disclosure.
- Patent Document 1 JP 2001-507368 JP (Patent Document 2) JP 2010-275291 JP (Patent Document 3) JP 2010-126523 JP (Patent Document 4) JP 2010-168294 JP
- the present invention provides a hair cosmetic comprising the following component (A), component (B) and water, wherein component (B) is dispersed in an aqueous phase, and the pH at 25 ° C. is 6 or less. To do.
- A Oxyalkylene polymer represented by the following general formula (a1)-(AO) n- (a1) [In the formula, A represents an alkylene group having 2 to 6 carbon atoms, and n represents a number of 50 to 30,000. However, n AOs consist of at least two types of alkyleneoxy groups, and the arrangement thereof may be either random polymerization or block polymerization. ]
- (B) Consists of a structural unit represented by the following general formula (b1) and a structural unit represented by the following general formula (b2), having a weight average molecular weight of 5,000 to 1,000,000 and an acid value of 5 or more Polymer of 400 or less-(CH 2 CR 1 COOH)-(b1) -(CH 2 CR 2 COOR 3 )-(b2) [Wherein, R 1 and R 2 represent a hydrogen atom or a methyl group, and R 3 represents a hydrocarbon group having 1 to 30 carbon atoms. ]
- the present invention provides a hair styling method that applies the above-described hair cosmetic composition to hair to prepare a hairstyle.
- the present invention provides use of the above-described hair cosmetic as a hair styling agent.
- the present invention has an appropriate rate of pressure-sensitive adhesiveness during drying so that a hairstyle can be incorporated even when set using a drier etc.
- the present invention relates to a hair cosmetic composition that has no feeling and has sufficient setting properties and re-styling properties.
- the inventor combined an oxyalkylene polymer having a specific structure with a (meth) acrylic acid polymer having a specific structure and a specific acid value in an acid form, and the pH of the aqueous phase was set to 6 or less.
- the latter (meth) acrylic acid polymer is present in a dispersed state in the aqueous phase, and after application to the hair, delays the onset of adhesive strength by drying and ensures time to make up the hairstyle. I found out that I can.
- this composition after drying, the oxyalkylene polymer and the (meth) acrylic acid polymer are mixed with each other, forming a uniform transparent film on the hair, and exhibiting sufficient setability and re-styling properties,
- the present inventors have found that it is a hair cosmetic that does not have a sticky or stiff feeling after styling.
- the weight average molecular weights of the component (A), the component (B), and other polymers shall mean polystyrene equivalent values measured by gel permeation chromatography (GPC).
- n is 50 or more from the viewpoint of obtaining sufficient self-selective adhesiveness after the hair cosmetic is dried, further 100 or more, further 150 or more, further 250 or more, further 1,000 The above is preferable.
- n is 50 or more from the viewpoint of obtaining sufficient self-selective adhesiveness after the hair cosmetic is dried, further 100 or more, further 150 or more, further 250 or more, further 1,000 The above is preferable.
- it is 30,000 or less, further 12,000 or less, further 4,000 or less, Further, it is preferably 3,000 or less, more preferably 2,500 or less.
- A is an alkylene group having 2 to 6 carbon atoms
- n AOs are composed of a combination of at least two alkyleneoxy groups.
- 4 is preferably a combination of two or more alkyleneoxy groups, more preferably a combination of 2 and 3 alkyleneoxy groups, that is, a combination of an ethyleneoxy group and a propyleneoxy group.
- the arrangement form of two or more kinds of AO in (AO) n may be either random polymerization or block polymerization.
- the component (A) oxyalkylene polymer has a propyleneoxy group ratio of 1% by mass or more in the whole component (A) from the viewpoint of developing self-selective adhesiveness after the hair cosmetic is dried. It is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the proportion of propyleneoxy groups in the whole component (A) is 60% by mass or less. It is preferably 50% by mass or less, more preferably 40% by mass or less, further 30% by mass or less, and further preferably 15% by mass or less.
- the weight average molecular weight of the oxyalkylene polymer of the component (A) is preferably 3,000 or more, more preferably 5,000 or more, further 7,000 or more, and further 1 from the viewpoint of obtaining sufficient self-selective adhesiveness after the hair cosmetic is dried. It is preferably 10,000 or more, more preferably 50,000 or more. In addition, while exhibiting sufficient self-selective adhesiveness after drying of the hair cosmetics, from the viewpoint of avoiding a decrease in usability accompanying an increase in viscosity, preferably 1.5 million or less, more preferably 600,000 or less, further 200,000 or less, Furthermore, 150,000 or less, Furthermore 100,000 or less are preferable.
- component (A) is not particularly limited, but it is preferably produced by ring-opening polymerization of a cyclic compound containing oxygen such as alkylene oxide, and either a base catalyst or an acid catalyst is used as the polymerization catalyst. May be.
- the content of the oxyalkylene polymer of the component (A) in the hair cosmetic composition of the present invention is the hair styling property and the hair style retention property after drying the hair cosmetic product.
- 20% by mass or less, further 15% by mass or less, further 10% by mass or less, and further 5% by mass or less are preferable.
- the hair cosmetic composition of the present invention does not exhibit tackiness before being applied to hair, it exhibits self-selective tackiness when dried after application.
- the component (B) needs to be dispersed in water in the hair cosmetic composition.
- the structure of component (B) is specified as follows.
- the polymer having the structural units (b1) and (b2) after the hair cosmetic is applied to the hair and dried, the hair cosmetic expresses self-selective adhesiveness, is excellent in setability and re-styling, and is stiff. From the viewpoint of eliminating the above, it is necessary that most of the structural unit (b1) exists in an unneutralized acid form.
- the structural unit (b1) may be partially neutralized, but the pH of the hair cosmetic must be 6 or less from the viewpoint of expressing self-selective adhesiveness, 5.9 or less, and further It is preferably 5.8 or less.
- the pH of the hair cosmetic is preferably 2 or more, more preferably 2.5 or more, more preferably 3 or more, and even more preferably 3.5 or more from the viewpoint of achieving good self-selective adhesiveness after the hair cosmetic is dried.
- the ratio of the equivalent of the base used for neutralization to the acid-type carboxy group before neutralization is 0 to 40%, more preferably 0 to 20%, furthermore 0 to 10% is preferred.
- R 1 and R 2 in the structural units (b1) and (b2) are a hydrogen atom or a methyl group.
- R 3 is a hydrocarbon group having 1 to 30 carbon atoms, and the hydrocarbon group may be saturated or unsaturated, and may be linear or branched.
- the carbon number of R 3 is preferably 2 or more from the viewpoint of making the hair cosmetic material less sticky, and from the viewpoint of improving the dispersibility of the component (B) in the aqueous phase. Hereinafter, it is preferably 16 or less, and more preferably 12 or less.
- the acid value of the component (B) is 5 or more, 30 or more, further 65 or more, and further 100 or more from the viewpoint of good self-selective adhesion after drying the hair cosmetic. It is preferable.
- the acid value of the component (B) is 400 or less, 370 or less, further 360 or less, Is preferably 325 or less, more preferably 180 or less.
- the catalog value is used for the acid value of component (B) if there is a catalog value.
- the catalog value is obtained by the third method described in “28. Acid value measurement method” of the Quasi-drug Raw Material Standard 2006 IV (Pharmaceutical Daily News).
- the mass ratio (b1) / (b2) of the constituent units (b1) and (b2) of the component (B) is: Preferably it is 1/99 or more, More preferably, it is 3/97 or more, More preferably, it is 8/92 or more, Preferably it is 49/51 or less, More preferably, it is 45/55 or less, More preferably, it is 41/59 or less is there.
- the mass ratio of (b1) and (b2) in component (B) can be calculated from the charged amount at the time of polymer synthesis, but it can also be calculated from the molecular weight of (b1) and the acid value of component (B). it can.
- component (B) it is preferable to calculate (b1) / (b2) according to the following formula using the molecular weight of (b1) and the acid value of component (B).
- the component (B) is preferably a non-crosslinkable polymer.
- the polymer of the component (B) may have a structural unit other than (b1) and (b2), and such a structural unit is 30% by mass or less of the entire component (B), and Is preferably 20% by mass or less, more preferably 15% by mass or less, and further preferably 10% by mass or less.
- structural units other than (b1) and (b2) include compounds having a vinyl structure such as vinyl pyrrolidone, vinyl caprolactam, and vinyl acetate, alkyl acrylamides, N, N-dialkyl acrylamides, and hydroxy (meth) acrylates.
- Nonionic structural units derived from compounds having a structure such as alkyl or alkoxy (meth) acrylate PEG; Cationic structural units derived from compounds such as N, N-dimethylaminopropylacrylamide, dimethylaminoethylacrylamide; Croton Anionic properties derived from monocarboxylic acids other than (meth) acrylic acid such as acids, dicarboxylic acids such as itaconic acid, maleic acid and fumaric acid, sulfonic acids such as vinyl sulfonic acid, and phosphoric acids such as acryloyloxyethyl phosphate Structural units of: carboxybetaine, sulfobe Examples include amphoteric structural units derived from compounds having a structure such as tine and phosphobetaine.
- the production method of component (B) is not particularly limited, but acrylic monomers capable of forming the above structural units are prepared by existing polymerization methods such as radical polymerization, living polymerization, living radical polymerization, functional group transfer polymerization (Group-Transfer polymerization). It can be produced by polymerization by ring-opening polymerization or the like.
- the structure of the polymer in this case is not particularly limited, and any of a random polymer, a block polymer, and a graft polymer may be used. From the viewpoint of exhibiting sufficient selective self-adhesion with the oxyethylene polymer, Polymers are preferred.
- the weight average molecular weight of the component (B) is 5,000 or more, preferably 7,000 or more, more preferably 10,000 or more, from the viewpoint of good self-selective adhesiveness after the hair cosmetic is dried. Further, from the viewpoint of suppressing the film formed on the hair from becoming hard and having excellent re-hairing properties, it is 1 million or less, preferably 800,000 or less, and more preferably 600,000 or less.
- Preferred polymers of such component (B) include Rubimer 100P (BASF Japan, INCI name: Acrylates® Copolymer), Rubimer Pro55 (BASF Japan, INCI name: Acrylates® Copolymer), Rubiflex Soft (BASF Japan) , INCI name: Acrylates copolymer), Rubygel FIT (BASF Japan, INCI name: Acrylates / C10-C30 methacrylate copolymer), Daitozol 5000SL (Daito Kasei Co., Ltd., INCI name: Acrylates copolymer).
- the content of the component (B) in the hair cosmetic composition of the present invention is 0.01% by mass or more, more preferably 0.05% by mass or more, from the viewpoint of improving hair styling properties and hairstyle retention after the hair cosmetic product is dried. Further, it is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and further preferably 1% by mass or more. Further, from the viewpoint of having moderate hair styling, 20% by mass or less, further 15% by mass or less, further 10% by mass or less, and further 5% by mass or less are preferable.
- the mass ratio (A) / (B) of the component (A) to the component (B) in the hair cosmetic of the present invention is self-selected after the hair cosmetic is dried by the interaction of the component (A) and the component (B).
- From the viewpoint of good adhesiveness 25/75 or more is preferable, 35/65 or more, and further 40/60 or more is preferable. Further, from the viewpoint of achieving good self-selective adhesion after drying the hair cosmetic, it is preferably 70/30 or less, more preferably 65/35 or less, and even more preferably 60/40 or less.
- the hair cosmetic composition of the present invention in addition to the components (A) and (B), another set polymer can be added as an optional component to further improve the set holding power.
- the polymer for the set include (methacryloyloxyethylcarboxybetaine / alkyl methacrylate) copolymers such as Yucaformer R205, Yukaformer 301 (Mitsubishi Chemical Co., Ltd.), RAM Resin (Osaka Organic Chemical Co., Ltd.); Diaformer Z-651 ( (Acrylates / Lauryl Acrylate / Stearyl Acrylate / Ethylamine Oxide Ethoxide) Copolymers such as Mitsubishi Chemical); Acrylic Acid / Acrylic Amide / Ethyl Acrylate such as Ultrahold 8 and Ultrahold Strong (BASF Japan) Copolymers; Alkyl acrylate / methacrylic acid / silicone copolymers such as Rubyflex Silk (BASF Japan); Polyurethanes such as Ruby Set
- Two or more kinds of the setting polymers other than these components (A) and (B) can be used in combination
- the content is from the viewpoint of maintaining the feature of excellent self-selective adhesiveness in the hair cosmetic composition of the present invention
- the total amount of components (A) and (B), and the mass ratio of the other set polymer [(A) + (B)] / [other set polymer] is preferably in the range of 60/40 or more, more preferably 70/30 or more, and even more preferably 80/20 or more. Further, it is preferably in a range of 99/1 or less, more preferably 97/3 or less.
- the hair cosmetic composition of the present invention contains water as a supporting medium, but can also be used in combination with lower alcohols (ethanol, isopropanol, etc.) and lactones, and these can be used alone or in combination. .
- water or a mixed system of water and ethanol is preferable from the viewpoint of ensuring dispersibility of the component (B).
- the content of the solvent other than water is preferably 20% by mass or less, more preferably 10% by mass or less, and further preferably 5% by mass or less from the viewpoint of securing the dispersibility of the component (B).
- a plasticizer component can be added to the hair cosmetic composition of the present invention for the purpose of imparting appropriate tackiness and re-tackiness properties without impairing self-selective tackiness.
- plasticizer components include polyhydric alcohols such as glycerin, 1,3-butanediol, and dipropylene glycol, and nonionic surfactants.
- a cosmetic oil can be added within a limit (0.1 to 10% by mass) that does not hinder the effects of the present invention.
- Such cosmetic oils include glycerides such as castor oil, cacao oil, mink oil, avocado oil, olive oil; waxes such as beeswax, whale wax, lanolin, carnauba wax; cetyl alcohol, oleyl alcohol, hexadecyl alcohol Higher alcohols such as lauryl alcohol, stearyl alcohol, isostearyl alcohol, 2-octyldodecanol; isopropyl myristate, hexyl laurate, cetyl lactate, propylene glycol monostearate, oleyl oleate, hexadecyl 2-ethylhexanoate, Esters of myristic acid octyldodecyl acid; liquid oils such as liquid paraffin, petrolatum, squalane, hydrogenated polyisobutene; dimethylpoly
- the hair cosmetic composition of the present invention can be added with a fragrance, a pigment, and a preservative and an antioxidant to prevent daily deterioration of the hair cosmetic composition in order to increase commercial value.
- a humidity control agent, a curing agent, an antistatic agent, an antifoaming agent, a dispersing agent, a thickening agent, an ultraviolet absorber, a colored dye, a dye fixing agent, a propellant and the like can be added.
- Aerosol hair cosmetics are manufactured by filling the above hair cosmetics together with a propellant into a pressure resistant container.
- the propellant include liquefied petroleum gas (LPG), dimethyl ether (DME), carbon dioxide gas, nitrogen gas, and mixtures thereof.
- LPG liquefied petroleum gas
- DME dimethyl ether
- CFCs such as HFC-152a can be used.
- the amount of the propellant is the mass ratio of the stock solution to the propellant in order to obtain good jetting properties and good adhesive properties.
- Stock solution / propellant 5/95 to 99/1, especially 20/80 to 95/5 The range of is preferable.
- the pressure in the pressure vessel is preferably adjusted to be 0.12 to 0.45 MPa at a temperature of 25 ° C.
- the hair cosmetic composition of the present invention can be suitably used as a hair styling agent.
- the hair cosmetic composition of the present invention is a non-sticky composition before it is applied to the hair, it is slowly applied to the hair while it is applied, blended, and made into a hairstyle. To express. For this reason, when applying to hair or when shaping with a brush, etc., it is easy to apply evenly to the entire hair, and it is free to handle and shape the hair without being caught even through the brush. Can do.
- the hair cosmetic becomes a firm transparent film having self-selective adhesiveness, and the hairs can be held with strong adhesion.
- a method for using the hair cosmetic composition of the present invention as a hair styling agent includes: i) a step of applying the hair cosmetic composition of the present invention to hair; and ii) a step of adjusting the hairstyle thereafter.
- the hair cosmetic composition of the present invention may be applied to wet hair or may be applied to dry hair.
- the hair cosmetic composition of the present invention is applied and dried or shaped using an iron or a dryer.
- a hair styling method in which hair is shaped using a brush or comb when it is dried or shaped using an iron or a dryer is further preferred. By such a method, the hair can be effectively shaped, and the shape can be maintained.
- a step of towel drying the wet hair may be performed before the step i).
- the hair cosmetic composition of the present invention is applied uniformly from the root or inside of the hair in step i), and further dried using a dryer in step ii) to increase the appearance and feel. It is preferable at the point which can do.
- the set hairstyle can be remade without using a dryer or iron, or the distorted hairstyle can be adjusted to the original shape.
- Such hair styling once set can be easily performed with fingers.
- a hair cosmetic comprising the following component (A), component (B) and water, wherein component (B) is dispersed in an aqueous phase, and the pH at 25 ° C. is 6 or less.
- (B) Consists of a structural unit represented by the following general formula (b1) and a structural unit represented by the following general formula (b2), having a weight average molecular weight of 5,000 to 1,000,000, Whose polymer is 5 or more and 400 or less-(CH 2 CR 1 COOH)-(b1) -(CH 2 CR 2 COOR 3 )-(b2) [Wherein, R 1 and R 2 represent a hydrogen atom or a methyl group, and R 3 represents a hydrocarbon group having 1 to 30 carbon atoms. ]
- the weight average molecular weight of the oxyalkylene polymer of component (A) is preferably 3,000 or more, more preferably 5,000 or more, still more preferably 7,000 or more, still more preferably 10,000 or more, and even more preferably 50,000 or more.
- the hair cosmetic composition according to ⁇ 1> which is preferably 1.5 million or less, more preferably 600,000 or less, further preferably 200,000 or less, further preferably 150,000 or less, and further preferably 100,000 or less.
- n AOs in the component (A) are preferably a combination of two or more alkyleneoxy groups having 2 to 4 carbon atoms, more preferably a combination of an ethyleneoxy group and a propyleneoxy group ⁇ 1 > Or ⁇ 2> hair cosmetics.
- the proportion of propyleneoxy groups in the whole component (A) is preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, and further preferably 10% by mass or more. In addition, it is preferably 60% by mass or less, more preferably 60% by mass or less, further preferably 50% by mass or less, further preferably 40% by mass or less, still more preferably 30% by mass or less, and further preferably 15% by mass or less.
- the hair cosmetic composition according to any one of ⁇ 1> to ⁇ 3>.
- the weight average molecular weight of the polymer of component (B) is preferably 7,000 or more, more preferably 10,000 or more, and preferably 800,000 or less, more preferably 600,000 or less ⁇ 1> to The hair cosmetic composition according to any one of ⁇ 4>.
- the content of component (A) is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, still more preferably 0.1% by mass or more, further preferably 0.5% by mass or more, and further preferably 1% by mass or more. Preferably, it is 20% by mass or less, more preferably 15% by mass or less, further preferably 10% by mass or less, and further preferably 5% by mass or less, according to any one of ⁇ 1> to ⁇ 5>. Hair cosmetics.
- the content of component (B) is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, still more preferably 0.1% by mass or more, further preferably 0.5% by mass or more, and further preferably 1% by mass or more. Preferably, it is 20% by mass or less, more preferably 15% by mass or less, further preferably 10% by mass or less, and further preferably 5% by mass or less, according to any one of ⁇ 1> to ⁇ 6>. Hair cosmetics.
- n is preferably 100 or more, more preferably 150 or more, still more preferably 250 or more, still more preferably 1,000 or more, and preferably 12,000 or less.
- the pH of the hair cosmetic is preferably 5.9 or less, more preferably 5.8 or less, preferably 2 or more, more preferably 2.5 or more, still more preferably 3 or more, and still more preferably 3.5 or more.
- the carbon number of R 3 in the general formula (b2) in the component (B) is preferably 2 or more, preferably 18 or less, more preferably 16 or less, and still more preferably 12 or less.
- the acid value of component (B) is preferably 30 or more, more preferably 65 or more, still more preferably 100 or more, preferably 370 or less, more preferably 360 or less, still more preferably 325 or less, The hair cosmetic according to any one of ⁇ 1> to ⁇ 10>, more preferably 180 or less.
- the mass ratio (A) / (B) of the component (A) to the component (B) is preferably 25/75 or more, more preferably 35/65 or more, and further preferably 40/60 or more.
- the mass ratio of the structural units other than (b1) and (b2) in the polymer of component (B) is preferably 30% by mass or less, more preferably 20% by mass or less, and still more preferably 15% by mass or less.
- the mass ratio (b1) / (b2) of (b1) and (b2), which are constituent units of component (B), is preferably 1/99 or more, more preferably 3/97 or more, and still more preferably 8
- ⁇ 15> The hair cosmetic according to any one of ⁇ 1> to ⁇ 14>, wherein the component (B) is preferably a non-crosslinkable polymer.
- a hair styling method comprising the following steps i) and ii): i) Step of applying the hair cosmetic composition according to any one of ⁇ 1> to ⁇ 15> to the hair ii) Step of adjusting the hairstyle thereafter
- the hair styling method according to ⁇ 16> wherein the hair is shaped while applying heat when the hairstyle is prepared in step ii).
- the weight average molecular weight of each polymer and the acid value of the polymer of component (B) were measured by the following methods.
- Detector Differential refractometer (attached to the GPC device trade name “HLC-8220GPC” (Tosoh Corporation)) Standard polystyrene samples: “TSKstandard POLYSTYRENE F-10” (molecular weight 102,000), F-1 (1020,000), A-1000 (870) (above, Tosoh Corporation), and “POLYSTYRENE STANDARD” (molecular weight 900,000, 3 10,000; Nishio Kogyo)
- Polymer acid value polymer solution or dispersion acid value / polymer concentration (%) x 100
- Synthesis Example 1 Synthesis of alkyl acrylate / acrylic acid (* 8) used in Comparative Example 6 Isopropyl alcohol in a 500 mL glass separable flask equipped with a Teflon crescent stirring blade, reflux condenser, and thermometer 82.1g was charged. Next, after reducing the pressure in the reactor to 20 kPa, a replacement operation was performed three times by blowing nitrogen at normal pressure. Thereafter, the flask was placed in an oil bath, and the temperature of the reaction solution was raised to 80 ° C. while stirring at 100 rpm.
- the mixture was further stirred for 6 hours while maintaining the internal temperature at 80 ° C., and the reaction solution was cooled to room temperature. Thereafter, isopropyl alcohol was distilled off to obtain a polymer.
- the obtained polymer had an acid value of 472 and a weight average molecular weight of 14,000.
- Examples 1 to 15 and Comparative Examples 1 to 6 The compositions shown in Tables 1 and 2 were prepared by a conventional method. The pH was adjusted using 2-aminomethylpropanol (AMP) and lactic acid so as to have a specified pH at 25 ° C. by a conventional method. These compositions were evaluated according to the following evaluation methods.
- AMP 2-aminomethylpropanol
- composition ⁇ Appearance of composition> When 20 g of each composition is put into a transparent screw tube No. 6 manufactured by Marum, and a striped paper with alternating white and black drawn at 4 mm intervals is placed behind the screw tube, and each composition is viewed from the front. Whether or not a stripe pattern in the back was visible was determined according to the following criteria.
- White turbidity The composition is white and turbid, and the stripe pattern is not visible.
- Slightly turbid The composition is white and turbid, but the stripe pattern is visible.
- Transparent The composition is not turbid and the stripe pattern is visible.
- the self-adhesive force of Example 1 is applied to the resistance force when the dry cast films on the PET film are bonded to each other with a force of 1 g / cm 2 and then peeled off at a peeling speed of 30 mm / sec in a T-shaped peeling form after 1 second.
- the self-adhesion power of score 5 and comparative example 1 was scored as 1, and scored in 5 levels and evaluated by sensory evaluation.
- ⁇ Adhesive expression time> Apply 1.0g of each composition to a 25g long, 7g Chinese straight hair trace, lightly stretch it, and then use a dryer (EH5311 made by Matsushita Electric Works) at a distance of 20cm while passing a finger once a second. The time until the finger feels sticky (unit: seconds) was defined as the stickiness expression time. If the time to tackiness is 15 seconds or longer, a hairstyle can be made sufficiently.
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Abstract
Description
(特許文献2)特開2010-275291号公報
(特許文献3)特開2010-126523号公報
(特許文献4)特開2010-168294号公報
-(AO)n- (a1)
〔式中、Aは炭素数2~6のアルキレン基を示し、nは50以上30,000以下の数を示す。ただし、n個のAOは、少なくとも2種のアルキレンオキシ基からなり、またその配列は、ランダム重合、ブロック重合のいずれでもよい。〕
-(CH2CR1COOH)- (b1)
-(CH2CR2COOR3)- (b2)
〔式中、R1及びR2は水素原子又はメチル基を示し、R3は炭素数1以上30以下の炭化水素基を示す。〕
本発明において、成分(A)、成分(B)及びその他の重合体の重量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)により測定したポリスチレン換算値をいうものとする。
一般式(a1)において、nは、毛髪化粧料の乾燥後に十分な自己選択粘着性を得る観点から、50以上であり、更には100以上、更には150以上、更には250以上、更には1,000以上であることが好ましい。また、毛髪化粧料の乾燥後に十分な自己選択粘着性を発揮すると共に、組成物の粘度増加に伴う使用性低下を回避する観点から、30,000以下であり、更には12,000以下、更には4,000以下、更には3,000以下、更には2,500以下であることが好ましい。
本発明の毛髪化粧料は、毛髪に塗布する前には粘着性を発現しないにも拘わらず、塗布後に乾燥すると自己選択粘着性を発現する。このためには、成分(B)は、毛髪化粧料中では水中に分散している状態であることが必要である。更に毛髪化粧料を毛髪に塗布した後、乾燥の進行によって成分(A)と成分(B)が均一に混ざり、自己選択粘着性を発現する必要がある。このような特徴を得るため、成分(B)の構造は以下のように特定される。
=(成分(B)の酸価)/1000/56.11×((b1)の分子量)×100
(成分(B)中の(b2)の質量%)=100-(成分(B)中の(b1)の質量%)
(b1)/(b2)=(成分(B)中の(b1)の質量%)/(成分(B)中の(b2)の質量%)
本発明の毛髪化粧料において、成分(A)及び(B)に加え、更に他のセット用ポリマーを任意成分として加えることで、更にセット保持力を向上させることができる。かかるセット用ポリマーとしては、ユカフォーマーR205、ユカフォーマー301(以上、三菱化学社)、RAMレジン(大阪有機化学社)等の(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)コポリマー;ダイヤフォーマーZ-651(三菱化学社)等の(アクリレーツ/アクリル酸ラウリル/アクリル酸ステアリル/メタクリル酸エチルアミンオキシド)コポリマー;ウルトラホールド8、ウルトラホールドStrong(以上、BASFジャパン社)等のアクリル酸/アクリル酸アミド/アクリル酸エチル共重合体;ルビフレックスSilk(BASFジャパン社)等のアクリル酸アルキル・メタクリル酸・シリコーン共重合体;ルビセットP.U.R.(BASFジャパン社)等のポリウレタン;ルビスコールPlus(BASFジャパン社)等のポリビニルカプロラクタム;アンフォーマー28-4910、アンフォーマーLV-71(以上、アクゾノーベル社)等の(オクチルアクリルアミド/アクリル酸ヒドロキシプロピル/メタクリル酸ブチルアミノエチル)コポリマー;アンフォーマーHC(アクゾノーベル社)等の(アクリル酸アルキル/オクチルアクリルアミド)コポリマー;レジン28-2930(アクゾノーベル社)等の(酢酸ビニル/クロトン酸/ネオデカン酸ビニル)コポリマー;ダイナムX(アクゾノーベル社)等のポリウレタン-14・AMP-アクリレーツコポリマー;アクアフレックスSF-40(アイエスピー・ジャパン社)等の(PVP/ビニルカプロラクタム/アクリル酸DMAPA)コポリマー;アクアフレックスFX-64(アイエスピー・ジャパン社)等の(イソブチレン/エチルマレイミド/ヒドロキシエチルマレイミド)コポリマー;スタイリーゼCC-10(アイエスピー・ジャパン社)等の(ビニルピロリドン/アクリル酸DMAPA)コポリマー;PVP/VA E-735(アイエスピー・ジャパン社)や、ルビスコールVA64P(BASFジャパン社)等の(ビニルピロリドン/酢酸ビニル)コポリマーなどが挙げられる。
本発明の毛髪化粧料は、水を支持媒体として含有するが、更に、低級アルコール(エタノール、イソプロパノール等)、ラクトン類等を併用することもでき、これらは単独で又は混合して用いることができる。これらのうち、成分(B)の分散性確保の観点から、水、又は水とエタノールの混合系が好ましい。また、水以外の溶媒の含有量は、成分(B)の分散性確保の観点から、20質量%以下が好ましく、更には10質量%以下、更には5質量%以下が好ましい。
本発明の毛髪化粧料中には、上記成分のほかに、自己選択粘着性を損なわないかたちで適度な粘着性、再粘着性を付与する目的で、可塑剤成分を加えることができる。このような可塑剤成分としては、グリセリン、1,3-ブタンジオール、ジプロピレングリコール等の多価アルコール類、非イオン界面活性剤等が挙げられる。
本発明の毛髪化粧料の剤型としては、特に制限はなく、透明液状、ローション状、乳液状、霧状(エアゾール、ノンエアゾール)、泡状(エアゾール、ノンエアゾール)などが可能である。
本発明の毛髪化粧料は、整髪剤として好適に使用することができる。本願発明の毛髪化粧料は、毛髪に塗布する前の状態では粘着性の無い組成物であるにもかかわらず、髪に塗布し、なじませ、ヘアスタイルを作っている間にゆっくりと粘着性を発現する。このため、毛髪に塗布する際や、ブラシ等を用いて形付けをする際には毛髪全体に均一に塗布しやすく、ブラシを通しても引っ掛かることがなく、自由に髪を取り扱い、形付けをすることができる。一方で、形付けをして毛髪化粧料が乾燥した後には、毛髪化粧料が自己選択粘着性を有するしっかりとした透明被膜になり、毛髪同士を強い粘着で保持させることができる。このため、本発明の毛髪化粧料の整髪剤としての使用方法、すなわち整髪方法としては、i)本発明の毛髪化粧料を毛髪に適用するステップ、ii)その後髪型を整えるステップを含む整髪方法が好ましい。本発明の毛髪化粧料は、濡れ髪に適用してもよく、乾き髪に適用してもよい。
(A) 下記一般式(a1)で表されるオキシアルキレン重合体
-(AO)n- (a1)
〔式中、Aは炭素数2~6のアルキレン基を示し、nは50以上30,000以下の数を示す。ただし、n個のAOは、少なくとも2種のアルキレンオキシ基からなり、またその配列は、ランダム重合、ブロック重合のいずれでもよい。〕
(B) 下記一般式(b1)で表される構成単位と、下記一般式(b2)で表される構成単位からなり、重量平均分子量が5,000以上100万以下であって、固形分の酸価が5以上400以下である重合体
-(CH2CR1COOH)- (b1)
-(CH2CR2COOR3)- (b2)
〔式中、R1及びR2は水素原子又はメチル基を示し、R3は炭素数1以上30以下の炭化水素基を示す。〕
i)<1>~<15>のいずれかに記載の毛髪化粧料を毛髪に適用するステップ
ii)その後髪型を整えるステップ
カタログ値等が無く、重量平均分子量を測定する必要がある場合は、GPC装置として、商品名「HLC-8220GPC」(東ソー社)を用い、以下の測定条件で測定した。
・サンプル濃度:0.25質量%
・サンプル注入量:100μL
・溶離液:クロロホルム
・流速:1.0mL/min
・測定温度:40℃
・カラム:商品名「K-G」(1本)+商品名「K-804L」(2本)(以上、Shodex社製)の計3本をつないで分析した。
・サンプル濃度:0.25質量%
・サンプル注入量:100μL
・溶離液:N,N-ジメチルホルムアミド溶液(60mmol/L H3PO4、50mmol/L LiBr)
・流速:1.0mL/min
・測定温度:40℃
・カラム:商品名「TSKgel α-M」(2本)(以上、東ソー社製)をつないで分析した。
・検出器:示差屈折計(GPC装置 商品名「HLC-8220GPC」(東ソー社)に付属)
・ポリスチレン標準サンプル:「TSKstandard POLYSTYRENE F-10」(分子量10.2万)、F-1(1.02万)、A-1000(870)(以上、東ソー社)、及び「POLYSTYRENE STANDARD」(分子量90万、3万;西尾工業社)
カタログ値等が無く、成分(B)の酸価を測定する必要がある場合は、日本医薬部外品原料規格2006に記載の酸価測定法(第2法)に従って測定を行った。成分(B)が溶液または分散液である場合は溶液又は分散液の酸価を測定し、成分(B)の濃度に応じて、以下の計算式でポリマーの酸価を算出した。
テフロン(登録商標)製三日月型撹拌翼、還流冷却器、温度計を備えた500mLガラス製セパラブルフラスコにイソプロピルアルコール82.1gを仕込んだ。次に、反応器内を20kPaに減圧した後、常圧の窒素を吹込む置換操作を3回行った。その後、フラスコをオイルバスにつけ、100rpmで撹拌しながら反応液を80℃まで昇温した。昇温を確認後、98質量%アクリル酸180.9g、アクリル酸ステアリル89.1g及びイソプロピルアルコール73.4gの混合溶液と、ジメチル2,2'-アゾビス(2-メチルプロピオネート)1.44g及びイソプロピルアルコール13.0gの混合溶液をそれぞれ別々に反応溶液に4時間かけて滴下した。内温を80℃に保ったまま更に1時間撹拌し、次にジメチル2,2'-アゾビス(2-メチルプロピオネート)0.72g及びイソプロピルアルコール6.5gの混合溶液を30分かけて反応溶液に滴下した。内温を80℃に保ったまま更に6時間撹拌し、反応溶液を室温まで冷却した。その後、イソプロピルアルコールを留去し、ポリマーを得た。得られたポリマーは酸価472、重量平均分子量14,000であった。
表1~2に示す組成物を常法により調製した。なお、pHは、2-アミノメチルプロパノール(AMP)及び乳酸を用いて、常法により25℃で規定のpHとなるように調整した。これらの組成物について、以下の評価方法に従い評価した。
各組成物20gをマルエム社製透明スクリュー管No.6に入れ、4mm間隔で白と黒を交互に描いた縞模様の紙をスクリュー管の背後に置き、各組成物を正面から見たときに背後の縞模様が見えるか否かを下記の基準で判定した。
白濁:組成物が白く濁り、縞模様が見えない
微濁:組成物が白く濁っているが、縞模様が見える
透明:組成物に濁りがなく、縞模様が見える
各組成物0.4gを、二軸延伸PETフィルム(東レ社製、ルミラーL-38-T60)上に30mm×20mmの範囲に塗布し、25℃、40%RHで24時間放置して乾燥させ、皮膜を作製した。このPETフィルム上の皮膜を25℃、40~65%RHの環境下において、以下の方法により皮膜の透明性及び自着力、他着力の評価を行った。
評価は7名のパネラーで行い、PETフィルム上の乾燥キャスト膜の1cm下方に6ポイントの明朝体で印刷した文書を置き、上から見たときの下の文字の見え方について、「文字が鮮明に読み取れる」/「文字が不鮮明だが読み取れる」/「文字が不鮮明で読み取れない」のいずれであるのかを択一的に選択させた。「文字が鮮明に読み取れる」/「文字が不鮮明だが読み取れる」/「文字が不鮮明で読み取れない」と答えたパネラーの人数を順に示す。
1g/cm2の力でPETフィルム上の乾燥キャスト膜同士を張り合わせて、1秒後にT字型剥離形式で剥離速度30mm/secで引き剥がしたときの抵抗力について、実施例1の自着力をスコア5、比較例1の自着力をスコア1として、5段階にスコア化して、官能により評価した。
1g/cm2の力で乾燥キャスト膜を指で押さえた後、0.1秒後に100mm/sで指を剥がすときに感じる抵抗力について、比較例3の他着力をスコア5、実施例1の他着力をスコア1として、5段階にスコア化して、官能により評価した。
長さ25cm、7gの中国人ストレート毛トレスに各組成物を1.0g塗布し、軽く伸ばした後に1秒間に1回の頻度で指を通しながら20cmの距離でドライヤー(松下電工製EH5311)を用いてブローを行い、手指に粘着性を感じるまでの時間(単位:秒)を粘着性発現時間とした。
粘着性発現までの時間が15秒以上であれば、十分にヘアスタイルを作りこむことができる。
長さ25cm、重さ3gの中国人ストレート毛トレスを水で濡らして、タオルドライ後、各組成物を1g適用し、毛髪を手ぐしで内巻きのカールを作りながら1分間ドライヤー乾燥して整髪を行った。整髪後のトレスについて、毛流れの揃いが良く、毛の細かい飛び出しがなく、思い通りにカールの形がつけられるという観点から評価を行った。評価は7名のパネラーに上記操作によって各組成物を用いて処理した際に「形付けしやすい」/「どちらともいえない」/「形付けしにくい」のいずれであるのかを択一的に選択させた。「形付けしやすい」/「どちらともいえない」/「形付けしにくい」と答えたパネラーの人数を順に示す。
整髪性の評価で使用し、手ぐしでカール付けした評価用トレスに対し、5回クシ通し(デルリンスムーズコーム#802(ストレート);滝川株式会社)をして毛束の形をくずした後、再度手指を使って、毛束をクシ通し前の形に戻す操作を行った。操作後のトレスについて、カールのだれがなく、毛の細かい飛び出しがなく、元の毛束の形に戻るという観点から評価を行った。評価は7名のパネラーに上記操作を行った際に「再整髪しやすい」/「どちらともいえない」/「再整髪しにくい」のいずれであるのかを択一的に選択させた。「再整髪しやすい」/「どちらともいえない」/「再整髪しにくい」と答えたパネラーの人数を順に示す。
整髪後のトレスの感触について、7名のパネラーに「べたつきがない」/「どちらともいえない」/「べたつきがある」のいずれであるのかを択一的に選択させた。「べたつきがない」/「どちらともいえない」/「べたつきがある」と答えたパネラーの人数を順に示す。
整髪後のトレスの感触について、7名のパネラーに「ごわつきがない」/「どちらともいえない」/「ごわつきがある」のいずれであるのかを択一的に選択させた。「ごわつきがない」/「どちらともいえない」/「ごわつきがある」と答えたパネラーの人数を順に示す。
*0:重量平均分子量2200、EO/PO質量比=20/80、ブロック重合(三洋化成社ニューポールPE-62)
(EO/PO質量比から算出した重合度:EOは10、POは30)
*1:重量平均分子量100,000、EO/PO質量比=90/10、ランダム重合(明成化学工業社EP1010N)
(EO/PO質量比から算出した重合度:EOは2000、POは200)
*2:重量平均分子量16,000、EO/PO質量比=80/20、ブロック重合(三洋化成社ニューポールPE-108)
(EO/PO質量比から算出した重合度:EOは300、POは55)
*3:重量平均分子量5,000、EO/PO質量比=70/30、ランダム重合(ADEKA社アデカポリエーテルPR5007)
(EO/PO質量比から算出した重合度:EOは80、POは26)
*4:重量平均分子量3,400、EO/PO質量比=40/60、ブロック重合(三洋化成社ニューポールPE-74)
(EO/PO質量比から算出した重合度:EOは30、POは35)
*5:R3=t-Bu,Et、酸価122~162、重量平均分子量60,000、R1=Me,R2=H(BASF社Luvimer Pro55)
*6:R3=Et、酸価283~350、重量平均分子量500,000、R1=Me,R2=H(BASF社Luviflex Soft)
*7:R3=C2-C22アルキル、酸価283~350、R1=CH3,R2=H,CH3(BASF社Luvigel FIT)
*8:R3=C18アルキル、酸価472、重量平均分子量14,000、R1,R2=H
Claims (12)
- 次の成分(A)、成分(B)及び水を含有し、成分(B)が水相中に分散されており、25℃でのpHが6以下である毛髪化粧料。
(A) 下記一般式(a1)で表されるオキシアルキレン重合体
-(AO)n- (a1)
〔式中、Aは炭素数2~6のアルキレン基を示し、nは50以上30,000以下の数を示す。ただし、n個のAOは、少なくとも2種のアルキレンオキシ基からなり、またその配列は、ランダム、ブロックのいずれでもよい。〕
(B) 下記一般式(b1)で表される構成単位と、下記一般式(b2)で表される構成単位からなり、重量平均分子量が5,000以上100万以下であって、酸価が5以上400以下である重合体
-(CH2CR1COOH)- (b1)
-(CH2CR2COOR3)- (b2)
〔式中、R1及びR2は水素原子又はメチル基を示し、R3は炭素数1以上30以下の炭化水素基を示す。〕 - 成分(B)の構成単位である(b1)及び(b2)の質量比(b1)/(b2)が、1/99以上49/51以下である請求項1に記載の毛髪化粧料。
- 成分(B)の重合体における(b1)及び(b2)以外の構成単位の質量割合が10%質量以下である請求項1又は2に記載の毛髪化粧料。
- 成分(B)が非架橋性重合体である請求項1~3のいずれかに記載の毛髪化粧料。
- 成分(A)のオキシアルキレン重合体の重量平均分子量が3,000以上150万以下である請求項1~4のいずれかに記載の毛髪化粧料。
- 成分(A)のオキシアルキレン基がエチレンオキシ基とプロピレンオキシ基である請求項1~5のいずれかに記載の毛髪化粧料。
- 成分(A)の全体中におけるプロピレンオキシ基の割合が1質量%以上60質量%以下である請求項1~6のいずれかに記載の毛髪化粧料。
- 成分(A)と成分(B)の質量比が25/75以上70/30以下である請求項1~7のいずれかに記載の毛髪化粧料。
- 成分(A)における一般式(a1)中のnが、250以上12,000以下である請求項1~8のいずれかに記載の毛髪化粧料。
- 成分(A)の含有量が、0.01質量%以上20質量%以下である請求項1~9のいずれかに記載の毛髪化粧料。
- 成分(B)の含有量が、0.01質量%以上20質量%以下である請求項1~10のいずれかに記載の毛髪化粧料。
- 次のステップi)及びii)を含む整髪方法。
i)請求項1~11のいずれかに記載の毛髪化粧料を毛髪に適用するステップ
ii)その後髪型を整えるステップ
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US11819930B2 (en) | 2016-11-14 | 2023-11-21 | Mitsubishi Gas Chemical Company, Inc. | Material for built-up edge formation and built-up edge formation method |
US11225625B2 (en) | 2017-05-25 | 2022-01-18 | Mitsubishi Gas Chemical Company, Inc. | Lubricant material for assisting machining process, lubricant sheet for assisting machining process, and machining method |
DE102017217467A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
DE102017217461A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
DE102017217455A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
DE102017217463A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
DE102017217458A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
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DE102017217454A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
DE102017217457A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
DE102017217456A1 (de) | 2017-09-29 | 2019-04-04 | Henkel Ag & Co. Kgaa | Mittel und Verfahren zur temporären Verformung keratinhaltiger Fasern |
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