WO2020067020A1

WO2020067020A1 - Hair oil

Info

Publication number: WO2020067020A1
Application number: PCT/JP2019/037293
Authority: WO
Inventors: 中村亮太; 坂西裕一
Original assignee: 株式会社ダイセル
Priority date: 2018-09-27
Filing date: 2019-09-24
Publication date: 2020-04-02

Abstract

A hair oil is provided which, when applied to the hair, imparts suppleness, lightness, a moist feeling, anti-frizz properties, and glossiness, and which is not prone to drip when held in the hand, is transparent and aesthetic, and has excellent spreadability. This hair oil contains a thickening agent (A) and an oil agent (B). The thickening agent (A) is represented in formula (1) below, and R¹in the formula is a group obtained by removing 4 hydrogen atoms from the structural formula of an aromatic group, or a group obtained by removing 4 hydrogen atoms from a structural formula in which 2 or more aromatic rings are bonded together via a simple bond or a linking group; R² is an aliphatic hydrocarbon group of 4 or more carbons; and, based on the total content of the thickening agent (A) and the oil agent (B), R³ contains 0.1-30.0 wt% of a compound that is a silicone functional group, and, based on the total content of the thickening agent (A) and the oil agent (B), contains 70.0-99.9 wt% of the oil agent (B). (1)... (R²-HNOC)_4-n-R¹-(CONH-R³)_n

Description

Hair oil

The present invention relates to a hair oil containing a thickener and an oil agent. Priority is claimed on Japanese Patent Application No. 2018-181264, filed on September 27, 2018, the content of which is incorporated herein by reference.

Hair oil is a kind of hair cosmetics used for the purpose of supplementing hair with oil, giving suppleness, moist feeling, ease of cohesion, luster and the like. As hair oils, 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 (see Patent Documents 1 and 2 and Non-Patent Document 1).

However, the above oil agent has a low viscosity at room temperature, and there is a problem that the oil easily falls from between fingers when it is picked up. As a method of solving this problem, there is known a method of adding a thickener to moderately thicken the oil agent. However, an oil composition obtained by thickening an oil with a conventional thickener (for example, a polystyrene-hydrogenated polyisoprene block copolymer described in Patent Document 3, having a number average molecular weight of 10,000 or more) is difficult to spread and spread on hair. It was difficult to apply thin and uniform.

In addition, if a hydrocarbon oil or a fatty acid ester oil is thickened by using a thickener having a specific structure (for example, a low molecular weight thickener described in Patent Document 4), it becomes sagging when picked up. It has been found that an oil composition that is difficult to drop and has excellent spreadability can be obtained. However, no effective low molecular weight thickener for silicone oil has been found.

JP-A-63-183517 JP-A-1-175923 JP-A-8-59765 WO 2015/083740

The inventor studied thickeners when silicone oil was used as an oil agent, and found that conventional thickeners are difficult to dissolve in silicone oil and should be used as thickeners for oil agents containing silicone oil. Turned out to be difficult. That is, a low molecular weight oil thickener effective for silicone oil has not been found, and a conventionally known thickener (gelling agent) imparts an appropriate viscosity to a hair oil using an oil containing silicone oil. That proved difficult.

Therefore, an object of the present invention is to provide a hair oil containing silicone oil as an oil agent, which can be applied to the hair to give suppleness, lightness, a moist feeling, ease of uniting, and a glossy feeling. An object of the present invention is to provide a hair oil which is hard to sag when taken, is transparent, has excellent appearance, and has excellent spreadability.

As a result of intensive studies to solve the above problems, the present inventors have found that a compound represented by the following formula (1) thickens an oil containing silicone oil to an arbitrary viscosity and stably maintains the viscosity. The hair oil containing the oil composition obtained by thickening the oil agent with this compound has an appropriate viscosity stably, so that it does not easily drip from between fingers when taken by hand, and has spreadability. It has been found that, when applied to hair, it is possible to impart flexibility, lightness, moist feeling, ease of uniting, and gloss. The present invention has been completed based on these findings.

That is, the present invention comprises a thickener (A) and an oil agent (B), wherein the thickener (A) is represented by the following formula (1)
(R ² -HNOC) _4-n -R ^1- (CONH-R ³ ) _n (1)
(Wherein, R ¹ is a group obtained by removing four hydrogen atoms from a structural formula of an aromatic ring, or a group obtained by removing four hydrogen atoms from a structural formula in which two or more aromatic rings are bonded via a single bond or a linking group. R ² is an aliphatic hydrocarbon group having 4 or more carbon atoms, R ³ is a silicone functional group represented by the following formula (2), and n is an integer of 1 to 4.)

(Wherein R ⁴ is a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, R ⁵ is a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, and R ⁶ to R ⁹ are the same or different. An alkyl group having 1 to 3 carbon atoms, m represents an integer of 0 to 10)
0.1 to 30.0% by weight based on the total content of the thickener (A) and the oil (B), and the oil (B) is a thickener ( A hair oil containing 70.0 to 99.9% by weight based on the sum of the contents of A) and the oil agent (B).

ヘア In the hair oil of the present invention, the oil agent (B) preferably contains silicone oil.

ヘア The hair oil of the present invention preferably has a silicone oil content of 30.0% by weight or more based on the total amount of the oil agent (B).

ヘア In the hair oil of the present invention, the sum of the contents of the thickener (A) and the oil agent (B) is preferably 10.0% by weight or more based on the total amount of the hair oil.

The hair oil of the present invention preferably has a viscosity of 0.1 to 10 Pa · s at a temperature of 25 ° C. and a shear rate of 10 s ⁻¹ .

ヘア Since the hair oil of the present invention contains the compound represented by the formula (1) as a thickener, it has an appropriate viscosity and can stably maintain the viscosity. Therefore, the hair oil of the present invention is less likely to sag when picked up and has excellent spreadability. That is, the usability of the hair oil is excellent. Further, the hair oil of the present invention has transparency and is excellent in aesthetic appearance. When the hair oil of the present invention is applied to hair, it can impart suppleness, lightness, moist feeling, ease of uniting, and glossiness to the hair.

<Hair oil>
The hair oil of the present invention is a composition containing a thickener (A) and an oil agent (B). In the hair oil of the present invention, a mixture of the thickener (A) and the oil agent (B) may be referred to as an “oil composition”. This oil composition is a mixture of the thickener (A) and the oil agent (B), and is particularly in a form in which the oil agent is thickened and stabilized (gelled) by the thickener. In the hair oil of the present invention, the combination of the oil compositions may be any combination in which the thickener (A) and the oil agent (B) are compatible, and the combination is not particularly limited. The hair oil of the present invention may have other components described below other than the thickener (A) and the oil agent (B). The hair oil of the present invention is not particularly limited as long as it is used by applying it to hair as a treatment or conditioner that does not wash away after shampooing or rinsing.

Incidentally, the term "thickener" in the hair oil of the present invention includes not only a thickener that imparts viscosity, but also a gelling agent that gels, and a stabilizer that stabilizes components of the composition uniformly. is there.

[Thickener (A)]
The thickener (A) in the hair oil of the present invention contains one or more compounds represented by the following formula (1) (hereinafter sometimes referred to as “compound (1)”).
(R ² -HNOC) _4-n -R ^1- (CONH-R ³ ) _n (1)
(Wherein, R ¹ is a group obtained by removing four hydrogen atoms from a structural formula of an aromatic ring, or a group obtained by removing four hydrogen atoms from a structural formula in which two or more aromatic rings are bonded via a single bond or a linking group. R ² is an aliphatic hydrocarbon group having 4 or more carbon atoms, R ³ is a silicone functional group represented by the following formula (2), and n is an integer of 1 to 4.)

(Wherein R ⁴ is a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, R ⁵ is a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, and R ⁶ to R ⁹ are the same or different. An alkyl group having 1 to 3 carbon atoms, m represents an integer of 0 to 10)

A bond extending to the left from R ⁵ in the formula (2) bonds to the nitrogen atom in the formula (1).

Examples of the aromatic ring for R ¹ in the formula (1) include an aromatic hydrocarbon ring such as benzene, naphthalene, and biphenyl; and an aromatic heterocyclic ring such as thiophene, pyrrole, pyrazole, imidazole, pyridine, and furan. it can.

The linking group is a divalent group having one or more atoms, and examples thereof include a divalent hydrocarbon group, an ether bond, an ester bond, a carbonate group, and a group in which a plurality of these groups are linked. it can.

Examples of the divalent hydrocarbon group include a linear or branched alkylene group having 1 to 18 carbon atoms such as a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, and a trimethylene group. , 1,2-cyclopentylene, 1,3-cyclopentylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene and the like having 3 to 18 carbon atoms. And cycloalkylene groups.

{Examples of the structural formula in which the two or more aromatic rings are bonded via a single bond or a linking group include biphenyl and benzophenone.

As the aromatic ring, an aromatic hydrocarbon ring is particularly preferred. R ¹ in the formula (1) is preferably a group obtained by removing four hydrogen atoms from the structural formula of an aromatic hydrocarbon ring, particularly a group obtained by removing four hydrogen atoms from the structural formula of benzene. Is preferred. In addition, in R ¹ in the formula (1), the four hydrogen atoms excluded are hydrogen atoms bonded to carbon constituting an aromatic ring.

Examples of the aliphatic hydrocarbon group having 4 or more carbon atoms for R ² in the formula (1) include a butyl, t-butyl, pentyl, hexyl, octyl, 2-ethylhexyl, decyl, dodecyl, myristyl, stearyl, nonadecyl group Linear or branched alkyl group having about 4 to 20 (preferably 6 to 18, more preferably 8 to 16) carbon atoms; 2-butenyl, 2-pentenyl, isopentenyl, 2-hexenyl, 3- A linear chain having about 4 to 20 carbon atoms (preferably 6 to 18, more preferably 8 to 16) such as hexenyl, 4-hexenyl, 5-hexenyl, 7-octenyl, 9-decenyl, 11-dodecenyl, and oleyl groups. Or a branched alkenyl group; a carbon number 4 such as a butynyl, pentynyl, hexynyl, octynyl, decynyl, pentadecynyl, octadecynyl group or the like; About 20 (preferably 6 to 18, more preferably 8 to 16), and the like straight chain or branched chain alkynyl groups. Among them, as R ² , a linear or branched alkyl group having 4 to 20 carbon atoms is preferable, a linear alkyl group having 6 to 18 carbon atoms is particularly preferable, and a linear alkyl group having 8 to 16 carbon atoms is preferable. Groups are most preferred. N in the formula (1) is preferably 2, 3, 4, more preferably 2 or 4, and particularly preferably 2. In Formula (1), when n is 1 or 2, a plurality of R ² may be the same or different.

Examples of the monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms for R ⁴ in the formula (2) include methyl, ethyl, propyl, butyl, t-butyl, pentyl, hexyl, octyl, 2-ethylhexyl, Examples thereof include linear or branched alkyl groups having 1 to 12 (preferably 1 to 8, more preferably 1 to 6, and more preferably 1 to 4) carbon atoms such as decyl and dodecyl groups.

Examples of the divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms for R ⁵ in the formula (2) include methylene, ethylene, propylene, butylene, t-butylene, pentylene, hexylene, octylene, and 2-ethylhexyl. Examples thereof include linear or branched alkylene groups having 1 to 12 (preferably 2 to 8, more preferably 3 to 6) carbon atoms such as xylene, decylene, and dodecylene groups.

Examples of the alkyl group having 1 to 3 carbon atoms for R ⁶ to R ⁹ in the formula (2) include a methyl, ethyl, propyl and isopropyl group.

M in the formula (2) represents an integer of 0 to 10, preferably an integer of 0 to 8, more preferably an integer of 1 to 6, and particularly preferably an integer of 1 to 4. When m is an integer of 2 to 10, a plurality of R ⁶ and R ⁷ may be the same or different.

When n is 2 to 4, a plurality of silicone functional groups (or R ³ ) represented by formula (2) in formula (1) may be the same or different.

The molecular weight of the compound (1) is, for example, about 500 to 2000, preferably 600 to 1900, particularly preferably 700 to 1800, and most preferably 800 to 1500. When the molecular weight of the compound (1) exceeds 2,000, the extensibility of the hair oil may deteriorate. On the other hand, when the molecular weight of the compound (1) is less than 500, the thickening effect tends to be reduced.

Examples of the compound in which R ¹ in the formula (1) is a group obtained by removing four hydrogen atoms from the structural formula of benzene include, for example, compounds represented by the following formulas (1-a) to (1-e) (benzene Compounds containing a group having an amide bond at the 1, 2, 4, and 5 positions of When the compounds represented by the following formulas (1-a) to (1-e) have a plurality of R ² , those R ² may be the same or different. Similarly, when it has two or more R < ³ >, those R < ³ > may be the same or different.

As the compound in which R ¹ in the formula (1) is a group obtained by removing four hydrogen atoms from the structural formula of benzene, the compound represented by the above formula (1-b) and / or the compound represented by the above formula (1-b) The compound represented by -c) is preferable because it has an excellent effect of appropriately thickening an oil agent (in particular, an oil agent containing silicone oil).

It is preferable that R ² and R ³ in the formula (1) be the following combinations in terms of an excellent effect of appropriately thickening an oil agent (particularly, an oil agent containing silicone oil).
[1] A combination in which R ² is a linear alkyl group having 4 to 10 carbon atoms and R ³ is a silicone functional group in which m in Formula (2) is 0 to 3 [2] A combination in which R ² is 4 carbon atoms to 10 is a linear alkyl group, R ³ is the formula (2) m is 4 to 10 in combination [3] (preferably 4-6) silicone functional group of R ² is - 10 to 16 carbon atoms A combination of (preferably 11 to 14 carbon atoms) a linear alkyl group and R ^{3 wherein} m in the formula (2) is a silicone functional group of 4 to 10 (preferably 4 to 6)

As the compound (1), among the compounds represented by the following formulas (1-1) to (1-16), the compounds having the following formulas (1-1) to (1-16) are preferable because of their excellent thickening stability. The compound represented by 1-9) is preferable in that it has an excellent effect of appropriately thickening the oil agent.

Compound (1) can form a fibrous self-assembly by self-association at an amide bond site by hydrogen bonding. Further, when the oil agent (B) contains a silicone oil, the R ³ group, which is a silicone functional group, has an affinity for the silicone oil contained in the oil agent (B). Therefore, the oil agent (B) (particularly, while maintaining transparency, by making the thickener (A) containing the compound (1) compatible with the oil agent (B) (particularly an oil agent containing silicone oil). Oil agent containing silicone oil) can be thickened moderately and stably over time. In particular, when R ³ in the formula (1) in the compound (1) is two or more different groups, the compound has appropriate crystallinity, so that the viscosity increases without being limited to the type of the oil agent (B). And can exert a thickening effect on a wider range of the oil agent (B). That is, it has a wide oil agent selectivity.

Compound (1) in which n in the formula (1) is 2 and R ¹ is a group obtained by removing four hydrogen atoms from the structural formula of benzene can be obtained, for example, by the following method.
First, benzenetetracarboxylic acid-1,2: 4,5-dianhydride and silicon for introducing a group represented by R ³ in the formula (1) [silicone functional group represented by the formula (2)] The compound is reacted with an amine (R ³ NH ₂ ) in an alcohol to obtain a compound represented by (HOOC) _4-n -R ^1- (CONH-R ³ ) _n as an intermediate. Next, the obtained compound is reacted with a compound (R ² NH ₂ ) for introducing a group represented by R ² in the formula (1) in an alcohol, and water is removed from the reaction system by azeotropic distillation. To obtain the compound (1).

In the above formula, R ² and R ³ are the same as described above. Compound (1) other than the compound represented by the above chemical formula can be synthesized by the same method.

The content of the compound (1) is 0.1 to 30.0% by weight based on the sum of the contents of the thickener (A) and the oil agent (B). The lower limit of the content is preferably 0.2% by weight, more preferably 0.3% by weight, further preferably 0.4% by weight, and particularly preferably 0.5% by weight. The upper limit of the content is preferably 20.0% by weight, more preferably 10.0% by weight, further preferably 8.0% by weight, and particularly preferably 5.0% by weight. When the content of the compound (1) is within the above range, an appropriate viscosity can be imparted to the oil agent, and an appropriate viscosity can be stably maintained. It is hard to sag from such and is excellent in spreadability.

として As the thickener (A), a known and commonly used thickener other than the compound (1) may be used together with the compound (1). The content of the compound (1) in the total amount of the thickener (A) is, for example, 30.0% by weight or more, preferably 50.0% by weight or more, more preferably 70.0% by weight or more, and further preferably 85% by weight or more. It is at least 0.0% by weight, particularly preferably at least 95.0% by weight. When the content of the compound (1) is within the above range, an appropriate viscosity can be imparted to the oil agent, and an appropriate viscosity can be stably maintained. It is hard to sag from and has excellent spreadability.

The content of the thickener (A) (the total amount when two or more kinds are contained) is, for example, 0.1 to 30.0% based on the sum of the contents of the thickener (A) and the oil agent (B). % By weight. The lower limit of the content is preferably 0.2% by weight, more preferably 0.3% by weight, further preferably 0.4% by weight, and particularly preferably 0.5% by weight. The upper limit of the content is preferably 20.0% by weight, more preferably 10.0% by weight, further preferably 8.0% by weight, and particularly preferably 5.0% by weight. When the content of the thickener (A) is within the above range, an appropriate viscosity can be imparted to the oil agent, and the appropriate viscosity can be stably maintained. It is hard to sag from a space or the like and has excellent spreadability.

含有 The content of the thickener (A) (when two or more kinds are contained, the total amount) is, for example, 0.1 to 10.0 parts by weight based on 100 parts by weight of the oil agent (B). The lower limit of the content is preferably 0.2 part by weight, more preferably 0.5 part by weight, further preferably 0.7 part by weight, particularly preferably 0.9 part by weight. The upper limit of the content is preferably 8.0 parts by weight, more preferably 6.0 parts by weight, further preferably 4.0 parts by weight, and particularly preferably 2.0 parts by weight. When the content of the thickener (A) is within the above range, an appropriate viscosity can be imparted to the oil agent, and the appropriate viscosity can be stably maintained. It is hard to sag from a space or the like and has excellent spreadability.

The content of the thickener (A) in the hair oil of the present invention is, for example, 0.05 to 30.0% by weight based on the total amount of the hair oil. The lower limit of the content is preferably 0.2% by weight, more preferably 0.3% by weight, further preferably 0.4% by weight, and particularly preferably 0.5% by weight. The upper limit of the content is preferably 20.0% by weight, more preferably 10.0% by weight, further preferably 8.0% by weight, and particularly preferably 5.0% by weight. When the content of the thickener (A) is within the above range, an appropriate viscosity can be imparted to the oil agent, and the appropriate viscosity can be stably maintained. It is hard to sag from a space or the like and has excellent spreadability.

[Oil (B)]
The oil agent (B) in the hair oil of the present invention is preferably an oil agent capable of imparting suppleness, lightness, moist feeling, ease of cohesion, luster, and the like by being applied to hair. The oil agent (B) preferably contains at least silicone oil. The oil agent (B) containing silicone oil is given an excellent thickening and stabilizing effect by the thickener (A) containing the compound (1) having a silicone functional group. As the oil agent (B), one type can be used alone, or two or more types can be used in combination. The oil agent (B) does not include the thickener (A).

Silicone oil is an oil (oil) composed of a synthetic polymer compound having a main skeleton formed by siloxane bonds. Examples of the silicone oil include decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, aminopropyldimethylsilicone, dimethylsilicone, and diphenylsilicone. Among them, a cyclic silicone having 4 to 10 ring members such as decamethylcyclopentasiloxane is preferred from the viewpoint of stability and safety when used as a hair oil. As the silicone oil, one type can be used alone, or two or more types can be used in combination.

The oil agent (B) may contain an oil other than the silicone oil (for example, a polar oil and a non-polar oil).

Examples of the polar oil include oils and fats (fruit oil and natural oil) such as olive oil and orange oil, waxes such as lanolin, and esters [isopropyl myristate, decyl oleate, cetyl octanoate, cetyl 2-ethylhexanoate]. Esters of fatty acids having 8 or more carbon atoms (preferably 8 to 25 carbon atoms) such as glycerin tri-2-ethylhexanoate and alcohols], higher fatty acids [12 or more carbon atoms such as lauric acid and oleic acid ( Preferred are fatty acids having 12 to 25 carbon atoms], and higher alcohols solid at room temperature [alcohols having 12 or more carbon atoms (preferably 12 to 25 carbon atoms) such as cetanol].

Examples of the non-polar oil include squalane, petrolatum, and hydrocarbon oils (such as isododecane and liquid paraffin).

In addition to the polar and non-polar oils, examples of the oil agent (B) include argan oil, cupuas oil, clary sage oil, tea tree oil, bergamot oil, jojoba oil, lavender oil, rosemary oil, shea oil, horse oil, and the like. May be blended.

As the oil agent (B), at room temperature (23 ° C.), it is preferable to use a liquid or pasty oil, but even a solid oil is used as long as a liquid hair oil can be prepared. Can be.

The content of silicone oil in the oil agent (B) is preferably, for example, 30.0% by weight or more, more preferably 50.0% by weight or more, and more preferably 70.0% by weight, based on the total amount of the oil agent (B). % By weight, more preferably at least 75.0% by weight, particularly preferably at least 90.0% by weight. When the content of the silicone oil is 30.0% by weight or more, the thickening effect of the thickener (A) containing the compound (1) having a silicone functional group tends to be enhanced.

The content of the silicone oil is, for example, 30.0 to 99.9% by weight based on the sum of the contents of the thickener (A) and the oil (B). The lower limit of the content is preferably 40.0% by weight, more preferably 50.0% by weight, further preferably 60.0% by weight, and particularly preferably 70.0% by weight. The upper limit of the content is preferably 99.6% by weight, more preferably 99.4% by weight, further preferably 99.2% by weight, and particularly preferably 99.0% by weight. When the content of the silicone oil is in the above range, the thickening effect of the thickener containing the compound (1) having a silicone functional group can be more exerted.

含有 The content of the oil agent (B) is 70.0 to 99.9% by weight based on the sum of the contents of the thickener (A) and the oil agent (B). The lower limit of the content is preferably 75.0% by weight, more preferably 80.0% by weight, further preferably 85.0% by weight, and particularly preferably 90.0% by weight. The upper limit of the content is preferably 99.6% by weight, more preferably 99.4% by weight, further preferably 99.2% by weight, and particularly preferably 99.0% by weight. When the content of the silicone oil is within the above range, the thickening agent containing the compound (1) having a silicone functional group can exhibit a thickening and stabilizing effect.

含有 The content of the oil agent (B) in the hair oil of the present invention (the total amount when two or more types are contained) is, for example, 50.0 to 99.9% by weight based on the total amount of the hair oil. The lower limit of the content is preferably 60.0% by weight, more preferably 70.0% by weight, further preferably 80.0% by weight, and particularly preferably 90.0% by weight. The upper limit of the content is preferably 99.6% by weight, more preferably 99.4% by weight, further preferably 99.2% by weight, and particularly preferably 99.0% by weight. When the content of the oil agent (B) is in the above range, the thickening effect of the thickener (A) containing the compound (1) having a silicone functional group can be more exerted.

The hair oil of the present invention may contain one or two components other than the thickener (A) and the oil agent (B) used in ordinary hair cosmetics (hair oil) as long as the effects of the present invention are not impaired. More than one species may be contained. Other components include, for example, surfactants, polyhydric alcohols, chelating agents, antibacterial agents, antioxidants, viscosity modifiers, astringents, antidandruff agents, hair restorers, ultraviolet absorbers, coloring agents (dye and Dyes such as pigments), fragrances, cosmetic ingredients (such as vitamins), and aerosol propellants. The content of the components (other components) other than the thickener (A) and the oil agent (B) in the hair oil of the present invention (the total amount when two or more components are contained) is, for example, 10.0% by weight or less, preferably It is at most 7.0% by weight, particularly preferably at most 5.0% by weight.

The sum of the content of the thickener (A) and the content of the oil agent (B) in the hair oil of the present invention is, for example, 90.0% by weight or more, preferably 93.0% by weight or more, based on the total amount of the hair oil of the present invention. It is preferably at least 95.0% by weight.

The hair oil of the present invention has an appropriate viscosity, and the viscosity at a temperature of 25 ° C. and a shear rate of 10 s ⁻¹ is appropriately selected within a range of, for example, 0.1 to 10 Pa · s, preferably 0.5 to 5 Pa · s. can do. When the viscosity exceeds the above range, it tends to be difficult to obtain spreadability. On the other hand, when the viscosity is lower than the above range, it tends to be difficult to prevent dripping when hair oil is picked up. The viscosity can be adjusted by adjusting the content of the thickener (A) within the above range.

ヘア The hair oil of the present invention may be in any state such as liquid, gel, and polyphase. Further, a mist shape, an aerosol shape or the like can be obtained by combination with a container.

ヘア The hair oil of the present invention can be produced, for example, through a step of making the thickener (A) compatible with the oil agent (B). More specifically, it can be manufactured by mixing and heating the total amount of the thickener (A) and the oil agent (B), making them compatible, and then cooling. If necessary, the other components may be added after cooling. It is also possible to mix the thickener (A) with a part of the oil agent (B), heat and compatibilize, cool, and then mix the remaining oil agent (B). it can.

The temperature at the time of compatibility is appropriately selected depending on the types of the thickener (A) and the oil agent (B) and is not particularly limited, but it is preferably not more than 100 ° C., and the boiling point of the oil agent (B) is 100 In the case where the temperature is not higher than about ° C, the boiling point is preferably about the same. Cooling after compatibilization is sufficient as long as it can be cooled to room temperature (for example, 25 ° C. or lower), and it may be gradually cooled at room temperature or may be rapidly cooled by ice cooling or the like.

Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. In addition, "-" in the following Table 1 shows that the component was not mix | blended. A thickener was obtained by the method of Synthesis Example 1-4 below.

Synthesis Example 1 <Production of compound (1-1)>
In a 150 mL four-neck separable flask equipped with a Dimroth condenser, a nitrogen inlet, a dropping funnel, and a thermocouple, 2 g of isobutanol (iBuOH), 16 g of cyclohexane (CHex), 1,2,4,5-benzenetetra 532 mg (2.4 mmol) of carboxylic acid-1,2: 4,5-dianhydride were charged. Thereafter, the temperature in the system of the four-neck separable flask was set at 25 ° C., and the charged compounds were mixed. Thereafter, 1.0 g (4.8 mmol) of 3-aminopropylpentamethyldisiloxane as silicon amine was added dropwise to the mixed compound in the four-neck separable flask over 5 minutes, and the mixture was aged for 2 hours. Thus, 1,4-diaminopropylpentamethyldisiloxane-2,5-benzenedicarboxylic acid as an intermediate of the compound (1-1) was obtained.

Next, 617 mg (4.8 mmol) of diisopropylcarbodiimide (DIC) was charged into a four-neck separable flask over 5 minutes, and aged for 10 minutes. Thereafter, 629 mg (4.8 mmol) of octylamine was added dropwise to the four-neck separable flask over 10 minutes, and the mixture was aged at 25 ° C. for 2 hours. Thereafter, aging was further performed at 40 ° C. for 18 hours. Thereafter, the pressure inside the four-neck separable flask was reduced to remove the solvent, and then the precipitated solid was separated by filtration to obtain 15 g of a crude product. 20 g of acetone was added thereto, followed by washing, and the product was separated and purified by column chromatography to obtain 200 mg of the target compound (1-1). The molecular weight of the compound (1-1) was 851.5.

The chemical formula in Synthesis Example 1 is as follows. The result of ¹ H-NMR measurement of the obtained compound (1-1) was as follows.

¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.5-9.5 (m, 2H), 3.41-3.45 (m, 8H), 1.10-1.82 (m, 28H), 0.80-0.91 (m, 6H), 0.41 -0.60 (m, 4H), 0.01-0.12 (m, 30H).

Synthesis Example 2 <Production of compound (1-4)>
Synthesis was performed in the same manner as in Synthesis Example 1 except that 3-aminopropylpentamethyldisiloxane was changed to 3-aminopropylundecamethylpentasiloxane, to obtain the following compound (1-4). The result of ¹ H-NMR measurement of the obtained compound (1-4) was as follows. The molecular weight of compound (1-4) was 1296.4.

¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.5-9.5 (m, 2H), 3.21-3.45 (m, 8H), 1.10-1.82 (m, 28H), 0.80-0.91 (m, 6H), 0.51 -0.70 (m, 4H), 0.11-0.19 (m, 75H).

Synthesis Example 3 <Production of compound (1-6)>
Synthesis was performed in the same manner as in Synthesis Example 2 except that octylamine was changed to dodecylamine to obtain the following compound (1-6). The result of ¹ H-NMR measurement of the obtained compound (1-6) was as follows. The molecular weight of compound (1-6) was 1408.6.

¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.5-9.5 (m, 2H), 3.21-3.45 (m, 8H), 1.10-1.82 (m, 44H), 0.80-0.91 (m, 6H), 0.51 -0.70 (m, 4H), 0.11-0.19 (m, 75H).

Synthesis Example 4 <Production of Comparative Compound>
Synthesis was performed in the same manner as in Synthesis Example 1 except that 3-aminopropylpentamethyldisiloxane was changed to 1-oleylamine-9,10-ene and octylamine to 2-ethylhexylamine, to obtain the following comparative compound.

Example 1
1 part by weight of the compound (1-1) obtained in Synthesis Example 1 as a thickener, and decamethylcyclopentasiloxane (trade name “KF-995”, manufactured by Shin-Etsu Chemical Co., Ltd.) as an oil agent (silicone oil); Hereinafter, 99 parts by weight of "cyclopentasiloxane" are mixed), heated and stirred at 80 ° C to make them compatible, and then cooled to 25 ° C to obtain a hair oil. The viscosity of the hair oil (1) at 25 ° C. (shear rate 10 s ⁻¹ ) was 2.0 Pa · s. The obtained hair oil was evaluated for usability, spreadability, and transparency by the following evaluation methods.

(Evaluation)
(1) Evaluation of usability and spreadability The hair oil obtained above was subjected to a sensory evaluation by ten female panelists. Specifically, the hair was washed using a shampoo (trade name "Revur", manufactured by Japan Gateway Co., Ltd.), rinsed well, and then dried to a half-dry state with a dryer. Then, take 5 g of the hair oil obtained above and blend it into the head hair. The usability of the hair oil (easiness of sagging when picked up by hand) and spreadability (smoothness of spreading) are as follows. The evaluation was made in five steps using the evaluation criteria, and a score was obtained.
[Evaluation criteria]
Very good: 5 points Good: 4 points Normal: 3 points Bad: 2 points Very poor: 1 point The following evaluation criteria were used to judge from the average of the obtained scores.
[Criteria]
：: 3 points or more △: 2 points ×: Less than 2 points

(2) Evaluation of Transparency The transparency of the hair oil obtained above was judged visually, and the transparency was evaluated according to the following criteria.
[Evaluation criteria]
〇: transparent △: translucent ×: cloudy

Examples 2 and 3, Comparative Example 1-4
A hair oil was obtained in the same manner as in Example 1 except that the formulation was changed to the formulation (unit: parts by weight) shown in Table 1 below, and these were evaluated in the same manner as in Example 1. In addition, as the oil agent of Comparative Examples 3 and 4, a mixture of 70 parts by weight of cyclopentasiloxane and 30 parts by weight of isododecane (trade name “Marcazole R”, manufactured by Maruzen Petrochemical Co., Ltd.) was used. In Comparative Example 2, no evaluation was performed because the comparative compound did not dissolve in the oil agent (cyclopentasiloxane).

The hair oils of the present invention (Examples 1 to 3) were found to be hair oils having excellent usability, spreadability, and transparency. On the other hand, the hair oils (Comparative Examples 1 to 4) in which the compound (1) of the present invention was not used as a thickening agent were easy to sag from between fingers and were poor in usability. As can be seen from Comparative Examples 2 and 3, the comparative compound in which the groups corresponding to R ² and R ³ in the formula (1) are composed of an aliphatic hydrocarbon is dissolved in a mixture of cyclopentasiloxane and isododecane. However, it did not dissolve in cyclopentasiloxane alone as a silicone oil.

As a summary of the above, the configuration of the present invention and its variations will be additionally described below.
[1] A thickener (A) and an oil agent (B), wherein the compound represented by the following formula (1) is used as the thickener (A), and the thickener (A) and the oil agent (B) 0.1 to 30.0% by weight based on the sum of the contents of the oil agent (B) and the oil agent (B) in an amount of 70.0% based on the sum of the contents of the thickener (A) and the oil agent (B). A composition comprising ～ 99.9% by weight.
(R ² -HNOC) _4-n -R ^1- (CONH-R ³ ) _n (1)
[2] The composition according to [1], wherein R ¹ in the formula (1) is a group obtained by removing four hydrogen atoms from the structural formula of an aromatic hydrocarbon ring.
[3] The composition according to [1], wherein R ¹ in the formula (1) is a group obtained by removing four hydrogen atoms from the structural formula of benzene.
[4] The composition according to [1], wherein the compound represented by the formula (1) is at least one compound selected from the compounds represented by the formulas (1-a) to (1-e). Stuff.
[5] The composition according to [1], wherein the compound represented by the formula (1) is a compound represented by the formula (1-b) and / or a compound represented by the formula (1-c). .
[6] The composition according to any one of [1] to [5], wherein R ² and R ³ in the formula (1) are the following (I), (II), or (III).
(I) R ² is a linear alkyl group having 4 to 10 carbon atoms, R ³ is a silicone functional group having m of 0 to 3 in the formula (2). (II) R ² is 4 to 10 carbon atoms. R ³ is a silicone functional group of the formula (2) wherein m is 4 to 10 (preferably 4 to 6); and (III) R ² is a C 10 to 16 (preferably Is a linear alkyl group having 11 to 14 carbon atoms, and R ³ is a silicone functional group having m of 4 to 10 (preferably 4 to 6) in the formula (2) [7] Formula (1) The composition according to [1], wherein the compound represented by formula (1) is at least one compound selected from compounds represented by formulas (1-1) to (1-16).
[8] The composition according to [1], wherein the compound represented by the formula (1) is at least one compound selected from the compounds represented by the formulas (1-1) to (1-9). Stuff.
[9] The composition according to any one of [1] to [8], wherein the compound represented by the formula (1) has a molecular weight of 800 to 1500.
[10] The composition according to any one of [1] to [9], wherein the oil agent (B) contains a silicone oil.
[11] The composition according to [10], wherein the content of the silicone oil is 30.0% by weight or more based on the total amount of the oil agent (B).
[12] The method according to any one of [1] to [11], wherein the sum of the contents of the thickener (A) and the oil agent (B) is 10.0% by weight or more based on the total amount of the composition. Composition.
[13] The composition according to any one of [1] to [12], wherein the viscosity at a temperature of 25 ° C. and a shear rate of 10 s ⁻¹ is 0.1 to 10 Pa · s.
[14] The composition according to any one of [1] to [13], which is a hair oil.
[15] A method for producing a hair oil, comprising producing a hair oil using the composition according to any one of [1] to [13].
[16] Use of the composition according to any one of [1] to [13] as a hair oil.

ヘア The hair oil of the present invention has an appropriate viscosity. Therefore, it is hard to sag when picked up and has excellent spreadability. When the hair oil of the present invention is applied to hair, it can impart suppleness, lightness, moist feeling, ease of uniting, and glossiness to the hair.

Claims

Including a thickener (A) and an oil agent (B),
The following formula (1) is used as the thickener (A).
(R 2 -HNOC) 4-n -R 1- (CONH-R 3 ) n (1)
(Wherein, R 1 is a group obtained by removing four hydrogen atoms from a structural formula of an aromatic ring, or a group obtained by removing four hydrogen atoms from a structural formula in which two or more aromatic rings are bonded via a single bond or a linking group. R 2 is an aliphatic hydrocarbon group having 4 or more carbon atoms, R 3 is a silicone functional group represented by the following formula (2), and n is an integer of 1 to 4.)

(Wherein R 4 is a monovalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, R 5 is a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, and R 6 to R 9 are the same or different. An alkyl group having 1 to 3 carbon atoms, m represents an integer of 0 to 10)
0.1 to 30.0% by weight based on the sum of the contents of the thickener (A) and the oil agent (B), and the oil agent (B) is contained in the thickener Hair oil containing 70.0 to 99.9% by weight based on the sum of the contents of (A) and oil agent (B).
ヘア The hair oil according to claim 1, wherein the oil agent (B) contains silicone oil.
The hair oil according to claim 2, wherein the content of the silicone oil is 30.0% by weight or more based on the total amount of the oil agent (B).
The hair oil according to any one of claims 1 to 3, wherein the sum of the contents of the thickener (A) and the oil agent (B) is 10.0% by weight or more based on the total amount of the hair oil.
The hair oil according to any one of claims 1 to 4, wherein the viscosity at a temperature of 25 ° C and a shear rate of 10 s -1 is 0.1 to 10 Pa · s.