WO2018186260A1 - Huile capillaire et son procédé de production - Google Patents

Huile capillaire et son procédé de production Download PDF

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Publication number
WO2018186260A1
WO2018186260A1 PCT/JP2018/012864 JP2018012864W WO2018186260A1 WO 2018186260 A1 WO2018186260 A1 WO 2018186260A1 JP 2018012864 W JP2018012864 W JP 2018012864W WO 2018186260 A1 WO2018186260 A1 WO 2018186260A1
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group
oil
thickener
hair
weight
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PCT/JP2018/012864
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English (en)
Japanese (ja)
Inventor
坂西裕一
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株式会社ダイセル
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Priority to JP2019511184A priority Critical patent/JPWO2018186260A1/ja
Publication of WO2018186260A1 publication Critical patent/WO2018186260A1/fr

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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
    • A61K8/73—Polysaccharides
    • 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

Definitions

  • the present invention contains a compatible agent of a thickener and an oil agent, is hard to fall off when picked up by hand, spreads smoothly when applied to hair, suppleness, lightness, moist feeling, unity
  • the present invention relates to a hair oil having an effect of imparting ease, luster and the like to hair, and a method for producing the same.
  • Hair oil is a type of cosmetic for hair that is used for the purpose of supplementing the hair with oil, giving it a suppleness, moist feeling, ease of cohesion, luster and the like.
  • vegetable oils such as camellia oil and olive oil, mineral oils such as liquid paraffin, higher fatty acids, silicone oils and the like have been used as hair oils (see Patent Documents 1 and 2 and Non-Patent Document 1).
  • the above-mentioned oil agent has a low viscosity at room temperature, and it has been a problem that it easily drops from between fingers when picked up.
  • a method for solving this problem a method is known in which a thickener is added to moderately thicken the oil agent.
  • a compatible material thickened with a conventional thickener for example, a polystyrene-hydrogenated polyisoprene block copolymer described in Patent Document 3
  • Patent Document 4 describes 1,2,3-propanetricarboxylic acid tris (2-methylcyclohexylamide) as a gelling agent for hydrophilic or lipophilic compounds.
  • 1,2,3-propanetricarboxylic acid tris (2-methylcyclohexylamide) is difficult to dissolve in the oil agent and it is difficult to use it as a thickener for the oil agent.
  • an object of the present invention is a hair oil that can be applied to hair to give suppleness, lightness, moist feeling, ease of uniting, glossiness, etc.
  • the object is to provide a hair oil that is hard to fall off and has excellent spreadability.
  • Another object of the present invention is a hair oil that can be applied to hair to give it suppleness, lightness, moist feeling, ease of cohesion, glossiness, and the like, and is transparent and excellent in aesthetics. It is intended to provide a hair oil that is resistant to dripping when taken on and has excellent spreadability.
  • Another object of the present invention is to provide a method for producing the hair oil.
  • a cellulose fiber having a group represented by the following formula (1-1) and / or a group represented by the following formula (1-2) that is, The modified cellulose fiber
  • the modified cellulose fiber is capable of thickening the oil to an arbitrary viscosity and maintaining the viscosity stably, and the hair oil containing the oil moderately thickened by the modified cellulose fiber was picked up by hand. It has been found that sometimes it is difficult to sag from between fingers or the like, has excellent spreadability, and can be applied to hair to give suppleness, lightness, moist feeling, ease of gathering, glossiness, and the like.
  • the present invention has been completed based on these findings.
  • this invention provides the hair oil containing the compatible material of an oil agent (A) and the following thickener (B).
  • Thickener (B) a modification having a structure in which a group represented by the following formula (1-1) and / or a group represented by the following formula (1-2) is bonded to a pyranose ring constituting the cellulose fiber.
  • Cellulose fiber (Wherein R 1 represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms, n represents 0 or 1, m represents an integer of 10 to 100, and m R 2 s are the same or different and represent carbon atoms. And represents an alkylene group having 2 to 4.
  • R 3 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms.
  • the compatibilizer of the oil agent (A) and the thickener (B) contains 0.1 to 40 parts by weight of the (B) per 100 parts by weight of the (A). Provide hair oil.
  • This invention also provides the manufacturing method of hair oil which obtains said hair oil through the process of making oil agent (A) and the following thickener (B) compatible.
  • Thickener (B) a modification having a structure in which a group represented by the following formula (1-1) and / or a group represented by the following formula (1-2) is bonded to a pyranose ring constituting the cellulose fiber.
  • Cellulose fiber (Wherein R 1 represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms, n represents 0 or 1, m represents an integer of 10 to 100, and m R 2 s are the same or different and represent carbon atoms. And represents an alkylene group having 2 to 4.
  • R 3 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms.
  • the oil agent (A) and the thickening agent (B) are compatible with each other at a ratio of 0.1 to 40 parts by weight with respect to 100 parts by weight of the (A).
  • a method for producing a hair oil is provided.
  • the hair oil of the present invention has an appropriate viscosity when the oil agent is thickened by the modified cellulose fiber, and the viscosity is stably maintained over time. In addition, it has excellent spreadability. That is, it is excellent in usability. Moreover, the hair oil of this invention has transparency and is excellent in aesthetics. When the hair oil of the present invention is applied to hair, the hair can be given a suppleness, lightness, moist feeling, ease of grouping, glossiness, and the like.
  • the hair oil of this invention contains the compatible material of an oil agent (A) and a thickener (B).
  • oil agent (A) and the thickener (B) can be used alone or in combination of two or more.
  • Oil agent (A) As the oil agent (A) in the present invention, any oil agent can be used without particular limitation as long as it is capable of imparting suppleness, lightness, moist feeling, ease of grouping, glossiness and the like by applying to the hair. Oils include polar oils, nonpolar oils, and mixtures thereof.
  • oils and fats such as olive oil, waxes such as lanolin, esters [isopropyl myristate, decyl oleate, cetyl octanoate, cetyl 2-ethylhexanoate, and glycerin tri-2-ethylhexanoate.
  • esters of fatty acids and alcohols having 8 or more carbon atoms preferably 8 to 25 carbon atoms
  • higher fatty acids preferably 12 to 25 carbon atoms
  • Fatty acids higher alcohols that are solid at normal temperature
  • alcohols having 12 or more carbon atoms (preferably, 12 to 25 carbon atoms) such as cetanol] and the like.
  • nonpolar oil examples include squalane, petrolatum, hydrocarbon oil (isododecane, liquid paraffin, etc.), chain or cyclic silicone oil, and the like.
  • thickener (B) In the thickener (B) in the present invention, the group represented by the following formula (1-1) and / or the group represented by the following formula (1-2) are bonded to the pyranose ring constituting the cellulose fiber.
  • a modified cellulose fiber having a structure hereinafter, simply referred to as “modified cellulose fiber”. Since the hair oil of the present invention contains the modified cellulose fiber as a thickener, the oil agent (A) can be appropriately thickened and the viscosity can be stably maintained. Moreover, if an oil agent (A) is transparent, it can thicken, maintaining the transparency.
  • R 1 represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms
  • n represents 0 or 1
  • m represents an integer of 10 to 100
  • m R 2 s are the same or different and represent carbon atoms.
  • R 3 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms.
  • the aliphatic hydrocarbon group for R 1 has 1 to 30 carbon atoms, preferably 3 to 30, more preferably 5 to 25, particularly preferably 10 to 20, and most preferably 15 to 20.
  • the aliphatic hydrocarbon group for R 1 includes a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group.
  • saturated aliphatic hydrocarbon group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, decyl group, and lauryl.
  • a linear or branched alkyl group such as a group, a myristyl group, and a stearyl group.
  • the unsaturated aliphatic hydrocarbon group is an aliphatic hydrocarbon group having at least one unsaturated bond, and an aliphatic hydrocarbon having at least one unsaturated bond selected from a double bond and a triple bond Groups.
  • the unsaturated aliphatic hydrocarbon group only needs to have at least one unsaturated bond, and may have one unsaturated bond or two or more.
  • the upper limit of the number of unsaturated bonds is, for example, 6, preferably 3.
  • the number of unsaturated bonds that the unsaturated aliphatic hydrocarbon group has is, for example, 1 to 6, preferably 1 to 3.
  • the group may have any configuration of cis and trans.
  • R 1 is preferably an unsaturated aliphatic hydrocarbon group, particularly preferably an aliphatic hydrocarbon group having at least one double bond, and most preferably 1 to 2 double bonds.
  • 6 preferably 1 to 3 linear or branched aliphatic hydrocarbon groups (for example, vinyl group, allyl group, 1-butenyl group, 4-hexenyl group, 5-hexenyl group, 7- Octenyl group, 9-decenyl group, 11-dodecenyl group, oleyl group and the like.
  • R 1 in particular, 1 to 30 (preferably 3 to 30, more preferably 5 to 25, particularly preferably 10) carbon atoms having 1 to 6 (preferably 1 to 3) double bonds.
  • 1 to 30 preferably 3 to 30, more preferably 5 to 25, particularly preferably 10
  • carbon atoms having 1 to 6 (preferably 1 to 3) double bonds preferably 1 to 3) double bonds.
  • linear or branched aliphatic hydrocarbon groups are preferred.
  • alkylene group having 2 to 4 carbon atoms in R 2 examples include linear or branched alkylene such as methylene, methylmethylene, dimethylmethylene, ethylene, propylene, trimethylene, and tetramethylene. Groups.
  • M represents an integer of 10 to 100, and the lower limit of m is preferably 15, particularly preferably 20, most preferably 25, and particularly preferably 30.
  • the upper limit of m is preferably 80, particularly preferably 70, most preferably 60, and particularly preferably 50.
  • Examples of the aliphatic hydrocarbon group having 1 to 20 carbon atoms in R 3 include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, An alkyl group having about 1 to 20 carbon atoms (preferably 1 to 10, particularly preferably 1 to 3) such as a hexyl group, a decyl group, or a dodecyl group; a carbon number such as a vinyl group, an allyl group, or a 1-butenyl group.
  • Alkenyl group having about 20 (preferably 2 to 10, particularly preferably 2 to 3); Alkynyl group having about 2 to 20 carbon atoms (preferably 2 to 10, particularly preferably 2 to 3) such as ethynyl group and propynyl group Etc.
  • an alkyl group (particularly preferably an alkyl group having 1 to 10 carbon atoms, particularly preferably an alkyl group having 1 to 3 carbon atoms) is preferable.
  • the thickener (B) has at least one group selected from the group represented by the above formula (1-1) and the group represented by the above formula (1-2) as a cellulose fiber. It contains a modified cellulose fiber having a structure bonded to a constituent pyranose ring (more specifically, bonded to a carbon atom constituting the pyranose ring).
  • the ratio of the group represented by the above formula (1-1) and the group represented by the above formula (1-2) in the modified cellulose fiber can be appropriately adjusted depending on the application, for example,
  • the average total degree of substitution of each group (that is, the sum of the average degree of substitution of the group represented by the formula (1-1) and the average degree of substitution of the group represented by the formula (1-2)) is: For example, it is 0.05 to 3.0.
  • the upper limit of the total degree of substitution is preferably 2.8, particularly preferably 2.7, and most preferably 2.6.
  • the lower limit of the total degree of substitution is preferably 0.1, more preferably 0.3, particularly preferably 0.5, most preferably 1.0, particularly preferably 1.5.
  • the degree of substitution of the group represented by the above formula (1-1) can be measured by the following method. 1.
  • the modified cellulose fiber is dissolved in dimethylacetamide and acylated with a carboxylic acid anhydride (eg acetic anhydride) in the presence of a catalyst (eg pyridine).
  • a catalyst eg pyridine
  • the obtained sample is reprecipitated with a poor solvent to remove unreacted components.
  • the total degree of substitution can be determined by dissolving in dimethylacetamide, saponifying with potassium hydroxide, and quantifying the amount of free fatty acid produced.
  • the completion of acylation can be confirmed by the absence of hydroxyl absorption in the vicinity of 3400 cm ⁇ 1 in the IR spectrum.
  • the degree of substitution (Dx) of the modified cellulose fiber having a configuration in which the group represented by the above formula (1-1) is bonded can be calculated as follows.
  • AV% % by weight of free fatty acid (for example, acetic acid) generated by saponification with respect to the sample weight before saponification
  • a + OH Molecular weight of free fatty acid corresponding to the acyl group introduced for the purpose of analysis (for example, when acetic anhydride is used as the carboxylic anhydride, the molecular weight of acetic acid (60.52 g / mol))
  • [AH] Difference in molecular weight between an acyl group introduced for analysis and a proton (for example, 42.037 g / mol when the acyl group is an acetyl group)
  • [XH] Difference in molecular weight between R 1 group and proton (for example, 264.45 g / mol when R 1 group is a cis-oleyl group)
  • G
  • the degree of substitution of the group represented by the above formula (1-2) can also be determined by the same method as that for the group represented by the above formula (1-1).
  • At least one of the hydroxyl groups bonded to the pyranose ring constituting the compound represented by the following formula (1) (In the formula, R 1 is the same as described above.
  • N represents 1) It can manufacture by making the carboxylic acid represented by these, or its derivative (s) react.
  • Examples of the cellulose fiber that is a raw material of the modified cellulose fiber include pulps obtained from natural plant materials such as wood, bamboo, hemp, jute, kenaf, cotton, beet, agricultural wastes, and cloth; regenerated cellulose fibers such as rayon and cellophane Is mentioned. Of these, pulp is preferable.
  • Examples of the pulp include chemical pulp obtained by chemically or mechanically pulping plant raw materials (for example, wood, cotton, etc.), deinked waste paper pulp, corrugated waste paper pulp, and magazine waste paper pulp. It is done.
  • kraft pulps derived from conifers having strong fiber strength for example, unbleached kraft pulps of conifers, unbleached kraft pulps exposed to oxygen from conifers, and bleached kraft pulps of conifers are preferable.
  • These raw materials are preferably subjected to delignification treatment or bleaching treatment as necessary. Moreover, you may perform the refiner process which beats the said raw material and makes it microfibril.
  • Examples of the carboxylic acid represented by the above formula (1) include saturated aliphatic carboxylic acids such as butanoic acid, pentanoic acid, caprylic acid, capric acid, lauric acid, myristic acid, stearic acid; crotonic acid, myristoleic acid , Monounsaturated aliphatic carboxylic acids such as palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid, erucic acid, nervonic acid; diunsaturated such as sorbic acid, linoleic acid, eicosadienoic acid, docosadienoic acid Aliphatic carboxylic acids; triunsaturated aliphatic carboxylic acids such as linolenic acid, pinolenic acid, eleostearic acid, dihomo- ⁇ -linolenic acid, eicosatrienoic acid; stea
  • Examples of the alcohol represented by the formula (1 ′) include saturated alcohols such as butanol, pentanol, 1-decanol, 1-dodecanol and stearyl alcohol; allyl alcohol, octadecadienol, docosenol, dodecedienol, oleyl alcohol , Unsaturated alcohols such as tridecenol and linoleyl alcohol.
  • the amount of the modifying agent used is, for example, 0.1 to 20 mol, preferably 0.4 to 10 mol, per 1 mol of glucose unit in the cellulose fiber.
  • the reaction may be stopped when the denaturant is used in excess and the reaction is carried out until a predetermined average substitution degree is reached.
  • the reaction for modifying the cellulose fiber with the group represented by the above formula (1-1) is preferably performed in the presence of a catalyst.
  • a catalyst include acid catalysts such as hydrochloric acid, sulfuric acid, and acetic acid, and basic catalysts. Among these, it is preferable to use a basic catalyst.
  • the basic catalyst examples include nitrogen-containing aromatic heterocyclic compounds such as pyridine and dimethylaminopyridine (DMAP); acyclic or cyclic tertiary amine compounds such as triethylamine, trimethylamine and diazabicyclooctane; potassium carbonate And alkali metal carbonates such as sodium carbonate.
  • nitrogen-containing aromatic heterocyclic compounds such as pyridine and dimethylaminopyridine (DMAP)
  • DMAP dimethylaminopyridine
  • acyclic or cyclic tertiary amine compounds such as triethylamine, trimethylamine and diazabicyclooctane
  • potassium carbonate alkali metal carbonates such as sodium carbonate.
  • the amount of the catalyst used is, for example, about 0.1 to 10 mol per 1 mol of glucose unit in cellulose fiber.
  • the reaction temperature of the modification reaction is, for example, about 20 to 160 ° C.
  • the reaction time is, for example, about 2 to 30 hours.
  • the modification reaction is preferably performed in a non-aqueous solvent.
  • the non-aqueous solvent include halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; ketones such as acetone and methyl ethyl ketone (MEK); diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, 1, 2 -Ethers such as dimethoxyethane and cyclopentylmethyl ether; Amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone; Saturated or unsaturated hydrocarbons such as pentane, hexane, heptane and octane; Aromatics such as benzene, toluene and xylene Hydrocarbons; and mixtures thereof.
  • halogenated hydrocarbons such as methylene chloride, chloroform and carbon t
  • the cellulose fiber is subjected to a crushing treatment, and a modifier is added thereto to cause the reaction, thereby improving the degree of substitution and better compatibility with the oil agent (A). It is preferable at the point which can provide.
  • the modified cellulose fiber having a structure in which the group represented by the above formula (1-2) is bonded to the pyranose ring constituting the cellulose fiber is a cellulose fiber [preferably constituting a cellulose fiber.
  • an oxidizing agent with the 6-position hydroxymethyl group (—CH 2 OH) of the pyranose ring]
  • an oxidized cellulose fiber in which a carboxyl group is bonded to the pyranose ring constituting the cellulose fiber is obtained (oxidation step). It can be produced by reacting at least one carboxyl group of the oxidized cellulose fiber with a polyetheramine as a modifier to form a salt (amine modification step).
  • the cellulose fiber it is possible to use the same cellulose fiber as in the case of producing a modified cellulose fiber having a structure in which the group represented by the formula (1-1) is bonded to the pyranose ring constituting the cellulose fiber. it can.
  • Examples of the oxidizing agent used in the oxidation step include hypohalous acid or a salt thereof (hypochlorous acid or a salt thereof, hypobromite or a salt thereof, hypoiodous acid or a salt thereof, etc.), halogenous acid Or a salt thereof (chlorous acid or a salt thereof, bromine acid or a salt thereof, iodic acid or a salt thereof), a perhalogen acid or a salt thereof (perchloric acid or a salt thereof, periodic acid or a salt thereof), halogen (chlorine, bromine, iodine), halogen oxides (ClO, ClO 2, Cl 2 O 6, BrO 2, Br 3 O 7 , etc.), nitrogen oxides (NO, NO 2, N 2 O 3 , etc.), Examples include peracids (hydrogen peroxide, peracetic acid, persulfuric acid, perbenzoic acid, etc.). These can be used alone or in combination of two or more.
  • the reaction between the cellulose fiber and the oxidizing agent is preferably performed in the presence of a catalyst.
  • bromides and iodides alkali metal bromides such as lithium bromide, potassium bromide and sodium bromide; alkali metal iodides such as lithium iodide, potassium iodide and sodium iodide; Alkaline earth metal bromides such as calcium iodide, magnesium bromide and strontium bromide; alkaline earth metal iodides such as calcium iodide, magnesium iodide and strontium iodide) may be used in combination.
  • alkali metal bromides such as lithium bromide, potassium bromide and sodium bromide
  • alkali metal iodides such as lithium iodide, potassium iodide and sodium iodide
  • Alkaline earth metal bromides such as calcium iodide, magnesium bromide and strontium bromide
  • alkaline earth metal iodides such as calcium iodide, magnesium iodide and strontium
  • the reaction solution in the alkaline range (for example, pH 9 to 12, preferably 10 to 11) in order to sufficiently proceed the oxidation reaction.
  • the carboxyl group bonded to the cellulose nanofiber is present in the form of a salt (for example, sodium salt) after completion of the oxidation step, it is preferable to add an acid to substitute the carboxyl group.
  • a salt for example, sodium salt
  • the polyetheramine as a modifier used in the amine modification step is represented, for example, by the following formula (2).
  • R 2 , R 3 and m are the same as above.
  • Polyetheramine can be used singly or in combination of two or more.
  • the weight average molecular weight of polyetheramine (converted to standard polystyrene by GPC) is, for example, 300 or more, preferably 500 or more, particularly preferably 1000 or more, and most preferably 1500 or more.
  • the upper limit of the weight average molecular weight is, for example, 5000, preferably 4000, and particularly preferably 3000.
  • the amine modification reaction is preferably performed in the presence of a solvent.
  • the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; saturated or unsaturated hydrocarbons such as n-hexane, n-octane, cyclohexane, and methylcyclohexane; dichloromethane, dichloroethane, chloroform, methylene chloride, four Halogenated hydrocarbons such as carbon chloride, fluorotrichloromethane, trichlorotrifluoromethane, hexafluorobenzene; tetrahydrofuran, 1,2-dimethoxyethane, cyclopentylmethyl ether, methyl-t-butyl ether (MTBE), 1,4-dioxane, methyl And ethers such as cellosolve; and mixtures thereof.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • the oxidized cellulose fiber obtained through the oxidation process is subjected to a crushing treatment, and a modifier is added to the reaction to improve the degree of substitution. It is preferable at the point which can provide more excellent compatibility.
  • the hair oil of this invention contains the compatible material of an oil agent (A) and a thickener (B).
  • the hair oil of the present invention can be produced, for example, through a process in which the oil (A) and the thickener (B) are compatible. More specifically, it can be manufactured by mixing and heating the oil agent (A) and the thickening agent (B) together, allowing them to dissolve, and then cooling. In addition, the thickener (B) is mixed with a part of the oil (A), heated and dissolved, cooled, and then mixed with the remaining oil (A). Can do.
  • the temperature at the time of compatibility is appropriately selected depending on the types of the oil agent (A) and the thickener (B), and is not particularly limited, but preferably does not exceed 100 ° C., and the boiling point of the oil agent (A) is 100. When the temperature is not higher than ° C., the boiling point is preferable.
  • the cooling after the compatibilization is only required to be able to cool to 25 ° C. or less, and may be gradually cooled at room temperature, or may be rapidly cooled by ice cooling or the like.
  • the amount of the thickener (B) used is, for example, 0.1 to 40 parts by weight, preferably 0.3 to 20 parts by weight with respect to 100 parts by weight of the oil (A). Parts, particularly preferably 0.5 to 10 parts by weight, most preferably 0.5 to 5 parts by weight.
  • the thickener (B) is used in the above range, an appropriate viscosity can be imparted to the oil agent (A), and when it is picked up by a hand, it is difficult to drop off and a hair oil excellent in spreadability can be obtained.
  • the compatible material of the oil agent (A) and the thickener (B) preferably contains 0.1 to 40 parts by weight of the (B) per 100 parts by weight of the (A). Is 0.3 to 20 parts by weight, particularly preferably 0.5 to 10 parts by weight, and most preferably 0.5 to 5 parts by weight.
  • the proportion of the thickener (B) in the present invention is, for example, 30% by weight or more, preferably 50% by weight or more, particularly preferably 70% by weight or more, and most preferably 85% or more.
  • the “thickener” in the present invention is a concept including a thickener that imparts viscosity, a gelling agent that gels, and a stabilizer that uniformly stabilizes the components of the composition.
  • the content of the compatible material is, for example, 20% by weight or more, preferably 30% by weight or more, more preferably 50% by weight or more, still more preferably 60% by weight or more, particularly preferably 80% by weight or more of the total amount of hair oil. Most preferably, it is 90 weight% or more, Most preferably, it is 95 weight% or more. In addition, the upper limit of content of the said compatible material is 100 weight%. Hair oils containing the above-mentioned compatible materials in the above range are excellent in spreadability while stably maintaining an appropriate viscosity, and give hair suppleness, lightness, moist feeling, ease of cohesion, glossiness, and the like. be able to.
  • the content of the oil agent (A) (the total amount when containing two or more) is, for example, 70.0 to 99.9% by weight of the total amount of the hair oil.
  • the upper limit of the content of the oil agent (A) is preferably 99.5% by weight, particularly preferably 99.0% by weight, and most preferably 98.5% by weight.
  • the lower limit of the content of the oil agent (A) is preferably 75.0% by weight, more preferably 80% by weight, particularly preferably 85.0% by weight, and most preferably 90.0% by weight.
  • the hair oil contains the oil agent (A) in the above range, the hair can be provided with suppleness, lightness, moist feeling, ease of grouping, glossiness, and the like.
  • the water content in the hair oil of the present invention is, for example, 1% by weight or less, preferably 0.2% by weight or less, based on the total amount of the hair oil.
  • the hair oil of the present invention may be substantially free of water.
  • the hair oil of the present invention may contain one or more other components in addition to the above-mentioned compatible material as long as the effects of the present invention are not impaired.
  • an aqueous component and a non-aqueous component may be sufficient, Preferably it is a non-aqueous component.
  • the other components include oily components other than the oil agent (A), surfactants, polyhydric alcohols, chelating agents, antibacterial agents, antioxidants, viscosity modifiers, astringents, antidandruff agents, and hair restorers. UV absorbers, colorants (pigments such as dyes and pigments), fragrances, beauty ingredients (vitamins, etc.), aerosol propellants and the like.
  • the content of the other components is, for example, about 10.0% by weight or less, preferably 7.0% by weight or less, particularly preferably 5.% or less, based on the total amount of the hair oil of the present invention. 0 wt% or less, most preferably 1.0 wt% or less.
  • the hair oil of the present invention has an appropriate viscosity, and the viscosity [at 25 ° C., at a shear rate of 10 s ⁇ 1 ] is, for example, 0.1 to 10 Pa ⁇ s (preferably 0.5 to 7 Pa ⁇ s, more preferably 1). Within a range of 0.0 to 6.5 Pa ⁇ s, particularly preferably 2.0 to 6.0 Pa ⁇ s), can be appropriately selected according to the application. When the viscosity exceeds the above range, the spreadability tends to be difficult to obtain. On the other hand, if the viscosity is below the above range, it tends to be difficult to prevent dripping when the hair oil is picked up. In addition, adjustment of a viscosity can be performed by adjusting content of a thickener (B) within the said range.
  • B thickener
  • the hair oil of the present invention may be in any state such as liquid, gel or multiphase. Moreover, it can also be set as mist form, aerosol form, etc. by the combination with a container.
  • Preparation Example 1 (Preparation of modified cellulose fiber) Refiner-treated softwood bleached kraft pulp (manufactured by Oji Paper Co., Ltd.) was dispersed in water to prepare a pulp water suspension having a solid content concentration of 1% by weight. The obtained pulp water suspension is fibrillated using a stone mill (trade name “Serendipitter MKCA6-3”, manufactured by Masuko Sangyo Co., Ltd., disk rotation speed: 1500 rpm) to obtain fibrillated cellulose. An aqueous suspension (solid content concentration: 1% by weight) was obtained.
  • Preparation Example 2 (Preparation of modified cellulose fiber) (Oxidation process) After adding 150 mL of water, 0.25 g of sodium bromide, and TEMPO (0.025 g) to 2 g of softwood pulp, and stirring and dispersing, 13% sodium hypochlorite aqueous solution (co-oxidant) was added to the pulp 1 The amount of sodium hypochlorite to be 5.2 mmol / g with respect to 0.0 g was added to start the reaction. Since the pH decreased with the progress of the reaction, the reaction was performed for 120 minutes while maintaining the pH at 10 to 11 by adding a 0.5N aqueous sodium hydroxide solution dropwise.
  • 0.1N hydrochloric acid was added for neutralization, followed by purification by repeated filtration and water washing to obtain oxidized cellulose whose fiber surface was oxidized. Subsequently, water contained in the oxidized cellulose was replaced with ethanol to obtain an oxidized cellulose suspension.
  • Example 1 (Preparation of hair oil) 2 parts by weight of the thickener (1) obtained in Preparation Example 1 and 98 parts by weight of isododecane as an oil agent are mixed, heated and stirred at 80 ° C. to dissolve them, and then cooled to 25 ° C. Solute (1) was obtained and this was designated as hair oil (1).
  • the viscosity of the obtained hair oil (1) at 25 ° C. and a shear rate of 10 s ⁇ 1 was 2.4 Pa ⁇ s.
  • Examples 2 to 5 and Comparative Examples 1 to 3 A hair oil was obtained in the same manner as in Example 1 except that the formulation was changed to the formulation shown in the following table (unit: parts by weight).
  • the average value of the obtained scores was further determined using the following three-step criteria. ⁇ : 3 points or more ⁇ : 2 points or more and less than 3 points ⁇ : Less than 2 points
  • Thickener (1) The thickener obtained in Preparation Example 1 was used.
  • Thickener (2) The thickener obtained in Preparation Example 2 was used.
  • the hair oil of the present invention has excellent usability, spreadability, and transparency.
  • the modified cellulose fiber in the present invention was not used as a thickener, the obtained hair oil was easily dropped from between the fingers, and the usability was poor. Moreover, it was inferior also in the point of transparency.
  • Thickener (B) a modification having a structure in which a group represented by the following formula (1-1) and / or a group represented by the following formula (1-2) is bonded to a pyranose ring constituting the cellulose fiber.
  • Cellulose fiber (Wherein R 1 represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms, n represents 0 or 1, m represents an integer of 10 to 100, and m R 2 s are the same or different and represent carbon atoms. And represents an alkylene group having 2 to 4.
  • R 3 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms.
  • the oil agent (A) is selected from the group consisting of a polar oil, a nonpolar oil, and a mixture thereof.
  • Oil (A) is a polar oil, oils and oils including olive oil, waxes including lanolin, esters [isopropyl myristate, decyl oleate, cetyl octanoate, cetyl 2-ethylhexanoate, tri-2 -Ester of fatty acid and alcohol having 8 or more carbon atoms (including 8 to 25 carbon atoms) including glyceryl ethylhexanoate, higher fatty acids [lauric acid, oleic acid, etc.
  • the oil agent (A) is a nonpolar oil, and is selected from the group consisting of squalane, petrolatum, hydrocarbon oil (including isododecane and liquid paraffin), and chain or cyclic silicone oil.
  • the hair oil according to any one of [3].
  • the aliphatic hydrocarbon group in R 1 is a saturated aliphatic hydrocarbon group, and is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl A linear or branched alkyl group selected from the group consisting of a group, a hexyl group, a decyl group, a lauryl group, a myristyl group, and a stearyl group, according to any one of [1] to [5] Hair oil.
  • the aliphatic hydrocarbon group in R 1 is an unsaturated aliphatic hydrocarbon group, an aliphatic hydrocarbon group having at least one unsaturated bond, and at least selected from a double bond and a triple bond It has one unsaturated bond, the number of unsaturated bonds is selected from at least 1, 2 or more, 1-6 or 1-3, and the upper limit of the number of unsaturated bonds is 6 or 3
  • the hair oil according to any one of [1] to [6].
  • the unsaturated aliphatic hydrocarbon group in R 1 is an aliphatic hydrocarbon group having at least one double bond, a linear or branched chain having 1 to 6 or 1 to 3 double bonds
  • An aliphatic hydrocarbon group comprising a vinyl group, an allyl group, a 1-butenyl group, a 4-hexenyl group, a 5-hexenyl group, a 7-octenyl group, a 9-decenyl group, an 11-dodecenyl group, and an oleyl group
  • the hair oil according to any one of [1] to [7], selected from the group.
  • R 1 is a straight chain having 1 to 6 or 1 to 3 double bonds and having 1 to 30, 3 to 30, 5 to 25, 10 to 20, or 15 to 20 carbon atoms.
  • alkylene group R 2 having 2 to 4 carbon atoms in the methylene group, methylmethylene group, dimethylmethylene group, an ethylene group, a propylene group, trimethylene group, straight-chain is selected from the group consisting of tetramethylene group or
  • m represents an integer of 10 to 100, the lower limit value of m is 15, 20, 25, or 30, and the upper limit value of m is 80, 70, 60, or 50.
  • the hair oil according to any one of [10].
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms in R 3 is methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, An alkyl group having 1 to 20, 1 to 10, or 1 to 3 carbon atoms including a group selected from the group consisting of hexyl, decyl, and dodecyl; from the group consisting of vinyl, allyl, and 1-butenyl An alkenyl group having 2 to 20, 2 to 10, or 2 to 3 carbon atoms including a selected group; 2 to 20, 2 to 10, or 2 to 3 carbon atoms including a group
  • the compatibility of the oil agent (A) and the thickener (B) is 0.1 to 40 parts by weight, 0.3 to 20 parts by weight of (B) per 100 parts by weight of (A).
  • the hair oil according to any one of [1] to [15] selected from the group consisting of 0.5 to 10 parts by weight.
  • the content of the compatible material is 20% by weight or more, 30% by weight or more, 50% by weight or more, 60% by weight or more, 80% by weight or more, 90% by weight or more, 95% by weight or more of the total amount of the hair oil.
  • the hair oil according to any one of [1] to [16] which is 100% by weight.
  • the content of the oil agent (A) (when two or more types are contained, the total amount thereof) is 70.0 to 99.9% by weight of the total amount of the hair oil, and the upper limit of the content of the oil agent (A) is 99.5 wt%, 99.0 wt%, or 98.5 wt%, and the lower limit of the content of the oil agent (A) is 75.0 wt%, 80 wt%, 85.0 wt%, or 90
  • a method for producing hair oil wherein the hair oil according to [1] is obtained through a step of compatibilizing the oil agent (A) and the following thickener (B).
  • Thickener (B) a modification having a structure in which a group represented by the following formula (1-1) and / or a group represented by the following formula (1-2) is bonded to a pyranose ring constituting the cellulose fiber.
  • Cellulose fiber (Wherein R 1 represents an aliphatic hydrocarbon group having 1 to 30 carbon atoms, n represents 0 or 1, m represents an integer of 10 to 100, and m R 2 s are the same or different and represent carbon atoms. And represents an alkylene group having 2 to 4.
  • R 3 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms.
  • the oil agent (A) and the thickener (B) are mixed in a ratio of 0.1 to 40 parts by weight with respect to 100 parts by weight of the above (A), [19] The manufacturing method of hair oil as described. [21] The total amount of the oil agent (A) and the thickener (B) are mixed and heated, and after dissolving, the cooling agent is included, or the thickener is included in part of the oil agent (A)
  • the method for producing a hair oil according to [19] or [20] which comprises mixing (B), heating and dissolving, cooling, and then mixing the remaining oil agent (A).
  • the temperature at the time of compatibilization does not exceed 100 ° C., or is about the boiling point when the boiling point of the oil agent (A) is 100 ° C. or lower. Any one of [19] to [21] The manufacturing method of hair oil as described. [23] Any of [19] to [22], wherein the cooling after the compatibilization is achieved by cooling to 25 ° C. or lower, gradually cooling at room temperature, or rapid cooling by ice cooling. The manufacturing method of the hair oil as described in one.
  • the hair oil of the present invention has an appropriate viscosity when the oil agent is thickened by the modified cellulose fiber, and the viscosity is stably maintained over time. In addition, it has excellent spreadability. That is, it is excellent in usability. Moreover, the hair oil of this invention has transparency and is excellent in aesthetics. When the hair oil of the present invention is applied to hair, the hair can be given a suppleness, lightness, moist feeling, ease of grouping, glossiness, and the like.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

Lorsqu'elle est appliquée sur les cheveux, l'huile capillaire selon la présente invention peut conférer souplesse, légèreté, hydratation, facilité de coiffure et brillance, ne tend pas à goutter lorsqu'elle est maintenue dans la main, et présente une excellente aptitude à l'étalement. L'huile capillaire selon l'invention contient un produit compatibilisé d'un agent huileux (A) et de l'épaississant (B) décrit ci-dessous. L'épaississant (B) est une fibre de cellulose modifiée ayant une structure dans laquelle un groupe représenté par l'expression (1-1) et/ou un groupe représenté par l'expression (1-2) est lié à un cycle pyranose constituant une fibre de cellulose (dans l'expression, R1 représente un groupe hydrocarboné aliphatique de 1 à 30 atomes de carbone, et n représente 0 ou 1.m représente un entier de 10 à 100, et les m R2 sont identiques ou différents et représentent un groupe alkylène de 2 à 4 carbones. R3 représente un groupe hydrocarboné aliphatique de 1 à 20 atomes de carbone.)
PCT/JP2018/012864 2017-04-04 2018-03-28 Huile capillaire et son procédé de production WO2018186260A1 (fr)

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008513480A (ja) * 2004-09-16 2008-05-01 イーストマン ケミカル カンパニー セルロース脂肪酸エステルを含むパーソナルケア製品
JP2009507926A (ja) * 2005-09-14 2009-02-26 イーストマン ケミカル カンパニー セルロース脂肪酸エステルを組み込んだパーソナルケア製品
JP2015527451A (ja) * 2012-07-31 2015-09-17 ハーキュリーズ・インコーポレーテッド 安定化多相水性組成物
WO2015174343A1 (fr) * 2014-05-14 2015-11-19 株式会社ダイセル Huile capillaire
JP2017014115A (ja) * 2015-06-26 2017-01-19 花王株式会社 皮膚化粧料
JP2017014116A (ja) * 2015-06-26 2017-01-19 花王株式会社 皮膚化粧料
JP2017019896A (ja) * 2015-07-08 2017-01-26 第一工業製薬株式会社 ゲル状組成物の製法およびそれにより得られたゲル状組成物
JP2017222610A (ja) * 2016-06-16 2017-12-21 日本製紙株式会社 発泡性エアゾール組成物
JP2018070851A (ja) * 2016-11-04 2018-05-10 株式会社服部商店 非水系粘度調整剤

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008513480A (ja) * 2004-09-16 2008-05-01 イーストマン ケミカル カンパニー セルロース脂肪酸エステルを含むパーソナルケア製品
JP2009507926A (ja) * 2005-09-14 2009-02-26 イーストマン ケミカル カンパニー セルロース脂肪酸エステルを組み込んだパーソナルケア製品
JP2015527451A (ja) * 2012-07-31 2015-09-17 ハーキュリーズ・インコーポレーテッド 安定化多相水性組成物
WO2015174343A1 (fr) * 2014-05-14 2015-11-19 株式会社ダイセル Huile capillaire
JP2017014115A (ja) * 2015-06-26 2017-01-19 花王株式会社 皮膚化粧料
JP2017014116A (ja) * 2015-06-26 2017-01-19 花王株式会社 皮膚化粧料
JP2017019896A (ja) * 2015-07-08 2017-01-26 第一工業製薬株式会社 ゲル状組成物の製法およびそれにより得られたゲル状組成物
JP2017222610A (ja) * 2016-06-16 2017-12-21 日本製紙株式会社 発泡性エアゾール組成物
JP2018070851A (ja) * 2016-11-04 2018-05-10 株式会社服部商店 非水系粘度調整剤

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