Novel amphiphilic substance with phosphorylcholine-like group, and cosmetics
Patent Information
- Application Number
- JP2023030845
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-03-01
- Publication Date
- 2025-12-05
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Abstract
Description
[Technical field]
[0001] The present invention relates to a compound which is a novel amphiphilic substance having a phosphorylcholine-like group, and to a cosmetic preparation using the same. [Background technology]
[0002] Surfactants are substances that have two opposing groups in their molecules, hydrophilic and hydrophobic groups, or polar and non-polar groups, and can have effects such as emulsification, dispersion, solubilization, wetting, cleaning, corrosion prevention, lubrication, and antistatic. Surfactants are used in a wide range of industries, but in recent years, high-value-added, highly functional surfactants have been attracting attention in fields related to living organisms, such as biochemistry, pharmaceuticals, sanitary materials, and cosmetics.
[0003] Surfactants used in the field of cosmetics include ionic and nonionic surfactants, and the surfactant to be blended is selected each time taking into consideration the intended use, feel when used, stability, etc. Among ionic surfactants, there are also betaine type surfactants that have both cationic and anionic sites in the molecule. In addition, gemini type surfactants (multi-chain, multi-hydrophilic group type amphiphilic substances with multiple hydrophobic chains and hydrophilic groups in one molecule), in which one-chain, one-hydrophilic group type surfactants are bonded via a spacer, have characteristics such as high surface activity represented by low critical micelle concentration and low Krafft point, and molecular association that easily forms higher-order structures such as vesicles.
[0004] On the other hand, the phosphorylcholine group is an amphoteric polar group with high hydrophilicity, and representative cosmetic raw materials having a phosphorylcholine group include phospholipids and lecithin. Gemini surfactants having structures similar to those derived from these natural products have been developed so far. For example, Non-Patent Document 1 reports on the synthesis of a gemini surfactant having a phosphorylcholine-like group as a hydrophilic group and its solution properties, and discloses that the surfactant has excellent interfacial properties.
[0005] Furthermore, in recent years, there has been a demand for the development of surfactants that take into consideration the feel of use and irritation to the skin, and there is a need for highly functional surfactants that are highly compatible with the living body, are low irritation, and are highly safe, while still meeting the characteristics required of a surfactant. In bio-related applications, mild characteristics to the living body, i.e., biocompatibility, are required, so it is preferable to have a surfactant in the biochemistry field (biosurfactant) or a structure similar to a biosurfactant. Among biosurfactants, there are surfactants derived from living bodies (such as lecithin), surfactants produced by microorganisms, and surfactants present in the living body. In addition, it is known that certain types of surfactants function effectively by directly acting on the living body (e.g., skin) in addition to functioning as a surfactant in a formulation. For example, Patent Document 1 shows that a compound containing a phosphorylcholine-like group has been developed, which exhibits a percutaneous absorption promoting effect and a moisturizing improving effect, and is useful for the living body. [Prior art documents] [Patent documents]
[0006] [Patent Document 1] JP 2011-213602 A [Non-patent literature]
[0007] [Non-Patent Document 1] Org.Lett.,Vol.1, No.9, pages 1347-1350 (1999) Summary of the Invention [Problem to be solved by the invention]
[0008] As described above, there is a further need for new surfactants that are biocompatible and have excellent surfactant performance.
[0009] As a result of intensive research, the inventors have discovered that compounds having a specific phosphorylcholine-like group are biocompatible and have high performance as surfactants, for example, for emulsification, dispersion, or solubilization, and have thus completed the present invention.
[0010] An object of the present invention is to provide a novel compound that is biocompatible and has excellent performance as a surfactant, and a cosmetic preparation using the same. [Means for solving the problem]
[0011] The present invention includes, but is not limited to, the embodiments listed below. [1] Formula (I): [ka] [In the formula, R 1 is a hydrocarbon group having 10 to 22 carbon atoms, R 2 is C 1-6 is an alkyl group, R 3 is C 1-6 is an alkyl group, R 4 -NR 5 R 6 , or -N + R 5 R 6 R 7 X - and R 5 is C 1-6 is an alkyl group, R 6 is C 1-6 is an alkyl group, R 7 is a hydrocarbon group having 10 to 22 carbon atoms, X - is an anion, and n is an integer from 2 to 30. A compound represented by the formula: [2] R 1is a straight-chain or branched-chain alkyl group, or a salt thereof. [3] R 1 is a linear alkyl group having 10 to 16 carbon atoms, or a salt thereof according to item [1] or [2]. [4] The compound or salt thereof according to any one of items [1] to [3], wherein n is an integer of 3 to 20. [5] R 2 is a methyl group, and R 3 is a methyl group, and R 5 is a methyl group, and R 6 is a methyl group, or a salt thereof. [6] R 7 is a linear or branched alkyl group, or a salt thereof. [7] R 7 is a linear alkyl group having 10 to 16 carbon atoms, or a salt thereof. [8] X - is a halide ion, or a salt thereof. [9] See below: [ka] The compound according to any one of items [1] to [8], or a salt thereof, selected from the group consisting of:
[10] A surfactant comprising the compound or salt thereof according to any one of items [1] to [9].
[11] A cosmetic preparation comprising the compound or salt thereof according to any one of items [1] to [9].
[12] Use of the compound or salt thereof according to any one of items [1] to [9] for producing a cosmetic preparation.
[13] A method for producing the compound or a salt thereof according to any one of items [1] to [9], reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (Ia): [ka] [In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , and n are as defined in section [1].] A manufacturing method comprising:
[14] The compound of formula (Ia) is reacted with R 7 - reacting with a compound represented by Xa to obtain a compound of formula (Ib-1): [ka] [In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , and n are as defined in item [1], and Xa is a halogen atom. The method according to item
[13] , further comprising: Effect of the Invention
[0012] According to the present invention, it is possible to provide a novel compound which is biocompatible and has excellent surfactant performance, for example, emulsification, dispersion, or solubilization, and a cosmetic preparation using the same. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0013] The present invention will be described in detail below.
[0014] compound The present invention relates to a compound of formula (I): [ka] [In the formula, R 1 is a hydrocarbon group having 10 to 22 carbon atoms, R 2 is C 1-6 is an alkyl group, R3 is C 1-6 is an alkyl group, R 4 -NR 5 R 6 , or -N + R 5 R 6 R 7 X - and R 5 is C 1-6 is an alkyl group, R 6 is C 1-6 is an alkyl group, R 7 is a hydrocarbon group having 10 to 22 carbon atoms, X - is an anion, and n is an integer from 2 to 30. Hereinafter, the compound or a salt thereof will be collectively referred to as the compound of the present invention or the present compound.
[0015] R 1 is a hydrocarbon group having 10 to 22 carbon atoms. The hydrocarbon group may be a saturated or unsaturated hydrocarbon group. The hydrocarbon group having 10 to 22 carbon atoms may be linear, branched, or cyclic. However, from the viewpoint of the performance of the surfactant (e.g., emulsification, solubilization, dispersion, etc.), in the case of a cyclic hydrocarbon group, an alicyclic ring is preferable to an aromatic ring. R 1 The hydrocarbon group of R is preferably a linear or branched hydrocarbon group, and more preferably a linear hydrocarbon group. The hydrocarbon group having 10 to 22 carbon atoms may be a hydrocarbon group having a structure in which a hydroxyl group (OH) is removed from a monovalent aliphatic alcohol (for example, an aliphatic alkyl group or alkenyl group). 1 The number of carbon atoms in the hydrocarbon group in is more preferably 10 to 20, and further preferably 10 to 18. The saturated hydrocarbon group may be, for example, an alkyl group. The unsaturated hydrocarbon group may be, for example, an alkenyl group or an alkynyl group. In the compound of formula (I), R 1can function as a hydrophobic group in a surfactant. 1 The hydrocarbon group is preferably a hydrophobic group.
[0016] R 1 In one embodiment, R is a saturated hydrocarbon group. The saturated hydrocarbon group may be linear or branched. 1 is preferably a linear or branched alkyl group. Examples of linear alkyl groups include decyl group (carbon number 10), dodecyl group (carbon number 12; also called lauryl group), tetradecyl group (carbon number 14; also called myristyl group), hexadecyl group (carbon number 16; also called cetyl group), octadecyl group (carbon number 18; also called stearyl group), and docosyl group (carbon number 22; also called behenyl group). Examples of branched alkyl groups include 16-methylheptadecyl group (carbon number 18; also called isostearyl group). R 1 is preferably a linear alkyl group having a carbon number of 10 to 16. Among these, a decyl group, a dodecyl group, a tetradecyl group, and a hexadecyl group are preferable, and a dodecyl group and a tetradecyl group are more preferable.
[0017] R 1 The hydrocarbon group may be unsaturated, and in this case, the unsaturation may be either carbon-carbon double bond unsaturation or carbon-carbon triple bond unsaturation, but is preferably carbon-carbon double bond unsaturation. The unsaturated hydrocarbon group having a carbon-carbon double bond is also called an alkenyl group. The number of unsaturations is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. When the number of unsaturations is 2 or more, it is preferable that all of them are carbon-carbon double bond unsaturation. Examples of the unsaturated hydrocarbon group include an oleyl group (also called a cis-9-octadecenyl group) and a linoleyl group.
[0018] R 2 is C 1-6 In the present specification, "C 1-6The term "alkyl group" means an alkyl group having 1 to 6 carbon atoms. 2 The alkyl group of R may be a linear alkyl group or a branched alkyl group. 2 The alkyl group of R is more preferably a linear alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group (n-butyl group, sec-butyl group, isobutyl group, tert-butyl group), a pentyl group (n-pentyl group, neopentyl group, etc.), and a hexyl group (n-hexyl group, etc.). 2 is C 1-3 It is preferably an alkyl group (a methyl group, an ethyl group, or a propyl group), more preferably a methyl group or an ethyl group, and even more preferably a methyl group.
[0019] R 3 is C 1-6 It is an alkyl group ("C 1-6 The definition of "alkyl group" is as above. 3 The alkyl group of R may be a linear alkyl group or a branched alkyl group. 3 The alkyl group of R is more preferably a linear alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group (n-butyl group, sec-butyl group, isobutyl group, tert-butyl group), a pentyl group (n-pentyl group, neopentyl group, etc.), and a hexyl group (n-hexyl group, etc.). 3 is C 1-3 It is preferably an alkyl group (a methyl group, an ethyl group, or a propyl group), more preferably a methyl group or an ethyl group, and even more preferably a methyl group.
[0020] R 2 and R 3 may be the same group or different groups. 2 and R 3 R is preferably the same group. 2 and R 3Each of the groups is preferably a methyl group, an ethyl group, or a propyl group, and more preferably a methyl group.
[0021] R 4 -NR 5 R 6 , or -N + R 5 R 6 R 7 X - That is, R 4 teeth, [ka] [wherein the wavy lines represent bonds to other moieties.] It is a group represented by the following formula:
[0022] R 5 is C 1-6 It is an alkyl group ("C 1-6 The definition of "alkyl group" is as above. 5 The alkyl group of R may be a linear alkyl group or a branched alkyl group. 5 The alkyl group of R is more preferably a linear alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group (n-butyl group, sec-butyl group, isobutyl group, tert-butyl group), a pentyl group (n-pentyl group, neopentyl group, etc.), and a hexyl group (n-hexyl group, etc.). 5 is C 1-3 It is preferably an alkyl group (a methyl group, an ethyl group, or a propyl group), more preferably a methyl group or an ethyl group, and even more preferably a methyl group.
[0023] R 6 is C 1-6 It is an alkyl group ("C 1-6 The definition of "alkyl group" is as above. 6 The alkyl group of R may be a linear alkyl group or a branched alkyl group. 6The alkyl group of R is more preferably a linear alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group (n-butyl group, sec-butyl group, isobutyl group, tert-butyl group), a pentyl group (n-pentyl group, neopentyl group, etc.), and a hexyl group (n-hexyl group, etc.). 6 is C 1-3 It is preferably an alkyl group (a methyl group, an ethyl group, or a propyl group), more preferably a methyl group or an ethyl group, and even more preferably a methyl group.
[0024] R 5 and R 6 may be the same group or different groups. 5 and R 6 R is preferably the same group. 5 and R 6 Each of the groups is preferably a methyl group, an ethyl group, or a propyl group, and more preferably a methyl group.
[0025] Here, R 2 , R 3 , R 5 and R 6 are preferably each independently selected from a methyl group, an ethyl group, and a propyl group, more preferably each independently selected from a methyl group and an ethyl group, and even more preferably each independently selected from a methyl group and an ethyl group. 2 , R 3 , R 5 and R 6 are all methyl groups.
[0026] R 7 is a hydrocarbon group having 10 to 22 carbon atoms. The hydrocarbon group may be a saturated or unsaturated hydrocarbon group. The hydrocarbon group having 10 to 22 carbon atoms may be linear, branched, or cyclic. However, from the viewpoint of the performance of the surfactant (e.g., emulsification, solubilization, dispersion, etc.), in the case of a cyclic hydrocarbon group, an alicyclic ring is preferable to an aromatic ring. R 7The hydrocarbon group of R is preferably a linear or branched hydrocarbon group, and more preferably a linear hydrocarbon group. The hydrocarbon group having 10 to 22 carbon atoms may be a hydrocarbon group having a structure in which a hydroxyl group (OH) is removed from a monovalent aliphatic alcohol (for example, an aliphatic alkyl group or alkenyl group). 7 The number of carbon atoms in the hydrocarbon group in is more preferably 10 to 20, and further preferably 10 to 18. The saturated hydrocarbon group may be, for example, an alkyl group. The unsaturated hydrocarbon group may be, for example, an alkenyl group or an alkynyl group. In the compound of formula (I), R 7 can function as a hydrophobic group in a surfactant. 7 The hydrocarbon group is preferably a hydrophobic group.
[0027] R 7 In one embodiment, R is a saturated hydrocarbon group. The saturated hydrocarbon group may be linear or branched. 7 is preferably a linear or branched alkyl group. Examples of linear alkyl groups include decyl group (carbon number 10), dodecyl group (carbon number 12; also called lauryl group), tetradecyl group (carbon number 14; also called myristyl group), hexadecyl group (carbon number 16; also called cetyl group), octadecyl group (carbon number 18; also called stearyl group), and docosyl group (carbon number 22; also called behenyl group). Examples of branched alkyl groups include 16-methylheptadecyl group (carbon number 18; also called isostearyl group). R 7 is preferably a linear alkyl group having a carbon number of 10 to 16. Among these, a decyl group, a dodecyl group, a tetradecyl group, and a hexadecyl group are preferable, and a dodecyl group and a tetradecyl group are more preferable.
[0028] R 7The hydrocarbon group may be unsaturated, and in this case, the unsaturation may be either carbon-carbon double bond unsaturation or carbon-carbon triple bond unsaturation, but is preferably carbon-carbon double bond unsaturation. The unsaturated hydrocarbon group having a carbon-carbon double bond is also called an alkenyl group. The number of unsaturations is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. When the number of unsaturations is 2 or more, it is preferable that all of them are carbon-carbon double bond unsaturation. Examples of the unsaturated hydrocarbon group include an oleyl group (also called a cis-9-octadecenyl group) and a linoleyl group.
[0029] R 1 and R 7 may be the same group or different groups. 1 and R 7 In one preferred embodiment, R 1 and R 7 Both R may be linear alkyl groups having the same number of carbon atoms. 1 and R 7 are preferably both independently selected from a decyl group, a dodecyl group, a tetradecyl group, and a hexadecyl group, and more preferably are selected from a dodecyl group and a tetradecyl group.
[0030] X - is an anion. 4 But -N + R 5 R 6 R 7 X - (if a quaternary amine is present), the compound requires a counter anion to achieve electrical neutrality. - is preferably a monovalent anion. - As for the cations, halide ions (F - , Cl - , Br - , I - ), hydroxide ion (OH -) and organic anions such as acetate ion. - is preferably a halide ion, and more preferably a bromide ion (Br - In a solution, the compound of formula (I) dissociates to form X - It may exist in a state not bound to (free state).
[0031] n is an integer of 2 to 30. n represents the number of methylene chains, and from the viewpoint of synthesis, in the compound of formula (I), it is at least 2. n is preferably 3 or more. n is preferably 25 or less, preferably 20 or less, and preferably 15 or less. n is more preferably 2 to 15, even more preferably 2 to 10, and still more preferably 3 to 10. In addition, n is also preferably 2, 3, 4, or 5. In another preferred embodiment, n is an integer of 3 to 20.
[0032] The compound of formula (I) may be in the form of a salt. For example, the compound of formula (I) may be in the form of a tertiary amine (NR 5 R 6 ), an acid may be added to the tertiary amine to form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, formic acid, and citric acid. In addition, the compound of formula (I) has an anionic phosphate and a cationic quaternary amine, and an ion (cation or anion) may be added to these moieties to form a salt. Examples of cations include Na + , K + Examples of metal cations include halide ions (F - , Cl - , Br - , I - ), inorganic anions such as hydroxide ion, and organic anions such as acetate ion.
[0033] In one embodiment, the compound of formula (I) may be a compound of formula (Ia). [ka] In the formula, R 1 , R 2 , R 3 , R 5 , R 6 and n are as defined in formula (I). The preferred embodiments of these substituents and n are the same as those described in formula (I).
[0034] In another embodiment, the compound of formula (I) may be a compound of formula (Ib). [ka] In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , X - and n are as defined in formula (I). The preferred embodiments of these substituents and n are the same as those described in formula (I).
[0035] Preferred embodiments of the compound of formula (I) are listed below. [Aspect 1-1] R 1 is a hydrocarbon group having 10 to 22 carbon atoms, and R 2 But, C 1-6 is an alkyl group, R 3 But R 2 Same as C 1-6 is an alkyl group, R 4 But -NR 5 R 6 and R 5 But, C 1-6 is an alkyl group, R 6 But R 5 Same as C 1-6 A compound of formula (I), wherein n is an alkyl group and n is 2 to 30. [Aspect 1-2] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-6 is an alkyl group, R 3 But, C1-6 is an alkyl group, R 4 But -NR 5 R 6 and R 5 But, C 1-6 is an alkyl group, R 6 But, C 1-6 A compound of formula (I), wherein n is an alkyl group and n is 2 to 30. [Aspect 1-3] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But, C 1-3 is an alkyl group, R 4 But -NR 5 R 6 and R 5 But, C 1-3 is an alkyl group, R 6 But, C 1-3 A compound of formula (I), wherein n is an alkyl group and n is 2 to 30. [Aspect 1-4] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But R 2 Same as C 1-3 is an alkyl group, R 4 But -NR 5 R 6 and R 5 But, C 1-3 is an alkyl group, R 6 But R 5 Same as C 1-3 A compound of formula (I), wherein n is an alkyl group and n is 2 to 10. [Aspect 1-5] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But R 2 Same as C 1-3 is an alkyl group, R 4 But -NR 5 R 6 and R5 But R 2 Same as C 1-3 is an alkyl group, R 6 But R 2 Same as C 1-3 A compound of formula (I), wherein n is an alkyl group and n is 2 to 10. [Aspect 1-6] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group or an ethyl group, and R 3 is a methyl group or an ethyl group, and R 4 But -NR 5 R 6 and R 5 is a methyl group or an ethyl group, and R 6 is a methyl group or an ethyl group, and n is 2 to 30. [Aspect 1-7] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group or an ethyl group, and R 3 is a methyl group or an ethyl group, and R 4 But -NR 5 R 6 and R 5 is a methyl group or an ethyl group, and R 6 is a methyl group or an ethyl group, and n is 2 to 10. [Aspect 1-8] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group, and R 3 is a methyl group, and R 4 But -NR 5 R 6 and R 5 is a methyl group, and R 6 is a methyl group, and n is 2 to 30. [Aspect 1-9] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group, and R 3 is a methyl group, and R 4But -NR 5 R 6 and R 5 is a methyl group, and R 6 is a methyl group, and n is 2 to 10. [Aspect 1-10] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group, and R 3 is a methyl group, and R 4 But -NR 5 R 6 and R 5 is a methyl group, and R 6 is a methyl group and n is 2, 3, 4 or 5. [Aspect 1-11] R 1 is a dodecyl group or a tetradecyl group, and R 2 is a methyl group or an ethyl group, and R 3 is a methyl group or an ethyl group, and R 4 But -NR 5 R 6 and R 5 is a methyl group or an ethyl group, and R 6 is a methyl group or an ethyl group, and n is 2 to 10.
[0036] Here, all of the above aspects 1-1 to 1-11 are R 4 Ga-NR 5 R 6 and also shows a preferred embodiment of the compound of formula (Ia).
[0037] [Aspect 2-1] R 1 is a hydrocarbon group having 10 to 22 carbon atoms, and R 2 But, C 1-6 is an alkyl group, R 3 But R 2 Same as C 1-6 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X -and R 5 But, C 1-6 is an alkyl group, R 6 But R 5 Same as C 1-6 is an alkyl group, R 7 is a hydrocarbon group having 10 to 22 carbon atoms, and X - is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-2] R 1 is a hydrocarbon group having 10 to 22 carbon atoms, and R 2 But, C 1-6 is an alkyl group, R 3 But R 2 Same as C 1-6 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But, C 1-6 is an alkyl group, R 6 But R 5 Same as C 1-6 is an alkyl group, R 7 But R 1 is a hydrocarbon group having 10 to 22 carbon atoms, the same as X - is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-3] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-6 is an alkyl group, R 3 But, C 1-6 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But, C 1-6 is an alkyl group, R 6 But, C 1-6 is an alkyl group, R 7 But, C 10-22 is an alkyl group, and X- is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-4] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But, C 1-3 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But, C 1-3 is an alkyl group, R 6 But, C 1-3 is an alkyl group, R 7 But, C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-5] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But R 2 Same as C 1-3 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But, C 1-3 is an alkyl group, R 6 But R 5 Same as C 1-3 is an alkyl group, R 7 But R 1 Same as C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 10. [Aspect 2-6] R 1 But, C 10-22 is an alkyl group, R2 But, C 1-3 is an alkyl group, R 3 But R 2 Same as C 1-3 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But R 2 Same as C 1-3 is an alkyl group, R 6 But R 2 Same as C 1-3 is an alkyl group, R 7 But, C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-8] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But R 2 Same as C 1-3 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But R 2 Same as C 1-3 is an alkyl group, R 6 But R 2 Same as C 1-3 is an alkyl group, R 7 But R 1 Same as C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-9] R 1 But, C 10-22 is an alkyl group, R 2 But, C 1-3 is an alkyl group, R 3 But R2 Same as C 1-3 is an alkyl group, R 4 But -N + R 5 R 6 R 7 X - and R 5 But R 2 Same as C 1-3 is an alkyl group, R 6 But R 2 Same as C 1-3 is an alkyl group, R 7 But R 1 Same as C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 10. [Aspect 2-10] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group or an ethyl group, and R 3 is a methyl group or an ethyl group, and R 4 But -N + R 5 R 6 R 7 X - and R 5 is a methyl group or an ethyl group, and R 6 is a methyl group or an ethyl group, and R 7 But, C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 30. [Aspect 2-11] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group or an ethyl group, and R 3 is a methyl group or an ethyl group, and R 4 But -N + R 5 R 6 R 7 X - and R 5 is a methyl group or an ethyl group, and R6 is a methyl group or an ethyl group, and R 7 But R 1 Same as C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 10. [Aspect 2-12] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group, and R 3 is a methyl group, and R 4 But -N + R 5 R 6 R 7 X - and R 5 is a methyl group, and R 6 is a methyl group, and R 7 But, C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2 to 10. [Aspect 2-13] R 1 But, C 10-22 is an alkyl group, R 2 is a methyl group, and R 3 is a methyl group, and R 4 But -N + R 5 R 6 R 7 X - and R 5 is a methyl group, and R 6 is a methyl group, and R 7 But R 1 Same as C 10-22 is an alkyl group, and X - is an anion (preferably a halide ion) and n is 2, 3, 4 or 5. [Aspect 2-14] R 1 is a dodecyl group or a tetradecyl group, and R 2 is a methyl group or an ethyl group, and R 3 is a methyl group or an ethyl group, and R4 But -N + R 5 R 6 R 7 X - and R 5 is a methyl group or an ethyl group, and R 6 is a methyl group or an ethyl group, and R 7 is a dodecyl group or a tetradecyl group, and X - is an anion (preferably a halide ion) and n is 2 to 10. [Aspect 2-15] R 1 is a dodecyl group or a tetradecyl group, and R 2 is a methyl group, and R 3 is a methyl group, and R 4 But -N + R 5 R 6 R 7 X - and R 5 is a methyl group, and R 6 is a methyl group, and R 7 is a dodecyl group or a tetradecyl group, and X - But, Br - and n is 2, 3, 4 or 5.
[0038] Here, all of the above aspects 2-1 to 2-15 are R 4 Ga-N + R 5 R 6 R 7 X - This also shows a preferred embodiment of the compound of formula (Ib).
[0039] The compound of formula (I) may be [ka] More preferably, the compound is selected from the group consisting of:
[0040] As described above, the compound of formula (I) is a compound having a phosphorylcholine-like group. In this specification, a phosphorylcholine-like group refers to a phosphorylcholine group (-O-PO3 - -(CH2)2-N + (CH3)3), specifically, -O-PO3 - -(CH2)2-N + (C 1-6 alkyl)2-.
[0041] The compound of formula (I) has a hydrophilic group and a hydrophobic group, and can function as a surfactant. Therefore, the compound of formula (I) is a novel amphiphilic substance having a phosphorylcholine-like group. In the compound of formula (I), the hydrocarbon group constitutes the hydrophobic group, and the phosphorylcholine-like group or a part thereof (P atom side or N atom side) can constitute the hydrophilic group. Specifically, for example, the compound of formula (I) can exhibit effects such as emulsification, dispersion, solubilization, wetting, cleaning, corrosion prevention, lubrication, and antistatic properties, and can exhibit high functionality, particularly in fields related to living organisms, such as biochemistry, pharmaceuticals, sanitary materials, and cosmetics. And, since the compound of formula (I) has a phosphorylcholine-like group, it is a surfactant with a structure similar to that derived from natural products, and therefore it is possible to obtain the same or similar action as phospholipids and lecithin, or even more. In addition, since the compound of formula (I) has a structure similar to that of a surfactant derived from a living organism, it is possible to obtain a surfactant that is highly biocompatible, low irritation, and highly safe, yet has high surface activity and is comfortable to use. In addition, the compound of formula (I) is expected to have not only surface activity but also direct effects on the living body (moisturizing effect, transdermal absorption promoting effect, etc.). In this specification, biocompatibility means that it is harmless and safe when used externally on the skin, particularly in cosmetics, and preferably does not give the user an unpleasant feeling when used (for example, stickiness, odor, etc.).
[0042] The present invention relates to a surfactant comprising a compound of formula (I) or a salt thereof. As described above, the compound of formula (I) has excellent surface activity and can be used as a surfactant.
[0043] As shown in the examples below, the compound of formula (I) has been demonstrated to have higher solubility in hydrophilic solvents (such as monohydric or polyhydric alcohols) than phosphatidylcholine, which is a phospholipid. Phosphatidylcholine has a structure in which two fatty acids serving as hydrophobic groups are bound to a phosphorylcholine group, with a glycerol structure sandwiched between them. On the other hand, the compound of formula (I) has one hydrocarbon group serving as a hydrophobic group on the phosphorus atom (P) side of the phosphorylcholine-like group, without the glycerol structure, and also has an aminoalkyl group bound to the nitrogen atom (N) side of the phosphorylcholine-like group, and it is presumed that these structures provide higher solubility than phosphatidylcholine and exhibit excellent surface activity.
[0044] Here, the compound of formula (Ia) has a structure in which an alkylaminoalkyl group is bonded to the nitrogen atom (N) side of a phosphorylcholine-like group, and therefore the surfactant ability is improved, making it possible to obtain an excellent preparation.
[0045] In addition, the compound of formula (Ib) has a structure in which an aminoalkyl group having a quaternary amine bonded to a long-chain hydrocarbon group is bonded to the nitrogen atom (N) side of the phosphorylcholine-like group. Such a structure can be said to be a structure in which the structure of a surfactant arranged on the phosphorus atom (P) side of the phosphorylcholine-like group and the structure of a surfactant arranged on the nitrogen atom (N) side of the phosphorylcholine-like group are bonded. In other words, the compound of formula (Ib) can be a gemini surfactant (a multi-chain multi-hydrophilic group type amphiphilic substance having multiple hydrophobic chains and hydrophilic groups in one molecule) in which one-chain one-hydrophilic group type surfactants are bonded by a spacer. Therefore, the compound of formula (Ib) is expected to have characteristics such as high surface activity represented by low critical micelle concentration and low Krafft point, and molecular association that easily forms higher-order structures such as vesicles.
[0046] synthesis In a preferred embodiment, the above compound can be prepared by the method shown in Scheme 1 below. [ka] [In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and n are as defined in formula (I), and Xa is a halogen atom.
[0047] In Scheme 1 above, 2-chloro-2-oxo-1,3,2-dioxaphospholane and R 1 The intermediate compound represented by formula (II) is obtained by reacting with an alcohol represented by -OH (Scheme 1-1). The reaction can be carried out in an organic solvent in the presence of a base such as an organic base. Examples of the organic base include triethylamine. Examples of the organic solvent include tetrahydrofuran. The reaction temperature can be, for example, from -20°C to 60°C. The reaction time can be, for example, from 1 to 6 hours. The compound of formula (II) may or may not be purified. Here, when the compound of formula (II) is purified, it can undergo hydrolysis with water vapor in the air, and the five-membered ring can be opened to generate alkyl 2-hydroxyethyl phosphate. Therefore, the compound of formula (II) can be preferably used in the next reaction without purification.
[0048] Next, the compound represented by formula (II) is reacted with the compound represented by formula (III) to obtain the compound represented by formula (Ia) (Scheme 1-2). The reaction can be carried out in an organic solvent. Examples of the organic solvent include tetrahydrofuran and acetonitrile. The reaction temperature can be, for example, 0°C to 100°C. The reaction can be carried out under reflux conditions. The reaction time can be, for example, 1 to 48 hours. The obtained compound of formula (Ia) can be purified by a conventional method (column chromatography, recrystallization, etc.). Alternatively, when a reaction to obtain formula (Ib-1) is further carried out, the compound of formula (Ia) may be used in the next reaction without purification. In the above manner, the compound of formula (Ia), which is one embodiment of the compound of formula (I), can be obtained.
[0049] Furthermore, the compound of formula (Ia) may be 7 By reacting with a compound represented by -Xa, a compound of formula (Ib-1), which is another embodiment of the compound of formula (I), can be obtained (Scheme 1-3). The reaction can be carried out in an organic solvent. Examples of the organic solvent include acetonitrile. The reaction temperature can be, for example, 0°C to 100°C. The reaction can be carried out under reflux conditions. The reaction time can be, for example, 1 to 24 hours. The obtained compound of formula (Ib-1) can be purified by a conventional method (column chromatography, recrystallization, etc.).
[0050] Here, Xa is a halogen atom, and specific examples thereof include F, Cl, Br, and I. Therefore, Xa - represents a halide ion, specifically, F - , Cl - , Br - , I - Xa is preferably Br.
[0051] The compound of formula (Ib-1) is X - corresponds to the compound of formula (Ib) in which X is a halide ion. -The compound of formula (Ib) in which is an anion other than a halide ion can be, for example, a halide ion (Xa - ) to an anion other than a halide ion (X - The anion exchange can be appropriately carried out using, for example, a generally known anion exchange resin.
[0052] As described above, the preparation of a compound of formula (I) or a salt thereof comprises reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (Ia): [ka] [In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , and n is as defined in formula (I). It is preferred that the compound contains
[0053] In addition, in the preparation of a compound of formula (I) or a salt thereof, a compound of formula (Ia) is reacted with R 7 - reacting with a compound represented by Xa to obtain a compound of formula (Ib-1): [ka] [In the formula, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and n are as defined in formula (I), and Xa is a halogen atom. It is also preferred that the composition further comprises:
[0054] Cosmetics The present invention relates to a cosmetic preparation containing a compound of formula (I) or a salt thereof. As described above, the compound of formula (I) can exhibit excellent surface activity and improve the stability of the cosmetic preparation. In addition, the compound of formula (I) is biocompatible and can provide a cosmetic preparation with little irritation. Furthermore, the compound of formula (I) can be incorporated to improve the feel of the cosmetic preparation. Thus, the compound of formula (I) or a salt thereof can be used to produce a cosmetic preparation, and can preferably be used as a surfactant.
[0055] The cosmetic preparation may be in any form, including a solution, a suspension, an emulsion composition (including O / W type, W / O type, W / O / W type, etc.), a powder-containing composition (including a powder-containing emulsion composition), etc.
[0056] The cosmetic may be a skin cosmetic or a hair cosmetic. The compound of formula (I) has good compatibility with the skin. Therefore, the cosmetic is preferably a skin cosmetic (skin cosmetic). In addition, the compound of formula (I) can be applied to cosmetics for all purposes, including skin care products and makeup products.
[0057] The skin cosmetic is not particularly limited and can be used as a cosmetic for various purposes, for example, a lotion, milky lotion, cream, beauty essence, hand cream, eye cream, body cream, makeup cosmetic, concealer, blush, eye shadow, eye color, lipstick, face powder, makeup base, foundation (e.g., liquid foundation, solid foundation, powder foundation), sunscreen, etc.
[0058] The hair cosmetic is not particularly limited and can be used as a cosmetic for various purposes, for example, hair cream, hair wax, hair rinse, hair mask, hair treatment, sunscreen for hair, etc.
[0059] The cosmetic preparation may contain any suitable cosmetic ingredient that can be incorporated into the cosmetic preparation. The cosmetic preparation may contain the compound of formula (I) or its salt, and other cosmetic ingredients (base, oil, active ingredient, water, etc.). Examples of cosmetic ingredients include oil, polymer, alcohol, surfactant, moisturizer, thickener, powder, pigment, film former, pH adjuster, anti-fading agent, antioxidant, defoamer, beauty ingredient, plant extract, preservative, fragrance, etc.
[0060] In one embodiment, the cosmetic preferably contains alcohols (monohydric or polyhydric alcohols). The alcohols are preferably liquid alcohols. Examples of monohydric alcohols include ethanol and isopropyl alcohol. Examples of polyhydric alcohols include 1,3-butylene glycol, propylene glycol, dipropylene glycol, and glycerin. The alcohols may be a solvent. As shown in the examples below, the compound of formula (I) has excellent solubility in alcohols. Therefore, a highly stable formulation can be obtained.
[0061] The cosmetic may contain an oil. Examples of the oil include hydrocarbon oils (such as squalane), ester oils (such as cetyl 2-ethylhexanoate and cetyl tri-2-ethylhexanoate), silicone oils (such as dimethicone and diphenylsiloxyphenyl trimethicone), higher alcohols (behenyl alcohol), fatty acids (such as stearic acid), fatty acid glyceryl (such as glyceryl stearate), and fatty acid sorbitan (sorbitan oleate). The oil may be liquid, solid, or semi-solid (paste).
[0062] The polymer may be a natural or synthetic polymer. Natural polymers include gums such as xanthan gum. Synthetic polymers include acrylic acid-based polymers such as (acrylates / alkyl acrylate (C10-30)) crosspolymer.
[0063] Examples of the powder include mica, talc, titanium oxide, zinc oxide, and iron oxide.
[0064] The content of the compound of formula (I) in the cosmetic is not limited to this, but when the total amount of the cosmetic is taken as 100 mass%, it can be 0.00001 to 50 mass%, preferably 0.0001 to 40 mass%, more preferably 0.001 to 30 mass%, and even more preferably 0.01 to 20 mass%.
[0065] The cosmetic can be produced by mixing the compound of formula (I) and the cosmetic ingredients. Here, the compound of formula (I) has excellent solubility in alcohols. Therefore, the compound of formula (I) may be dissolved in alcohols and the solution may be mixed with other ingredients. This allows a uniform and stable preparation to be obtained. EXAMPLES
[0066] The compounds of the present invention will be described below with reference to examples, but the present invention is not limited to these examples.
[0067] Measurement equipment and conditions NMR measurements are 1 H NMR: BRUKER ULTRASHIELDTM 300MHz was used, and the standard substance was DSS (sodium 3-(trimethylsilyl)-1-propanesulfonate) or TMS (tetramethylsilane). ESI-MS was used JEOL JMS-T100LC. Elemental analysis was performed using PERKIN-ELMER 24002 CHNS / O.
[0068] Synthesis Example 1: Synthesis of N,N-dimethyl-N-[(N',N'-dimethylamino)propyl]ammonium ethyl dodecyl phosphate (Compound 1: C12PCAm) [ka] In a four-neck flask, 1-dodecanol (5.00 g, 1.0 equivalent) and triethylamine (1.0 equivalent) were added and dissolved in about 50 mL of tetrahydrofuran. Then, 2-chloro-2-oxo-1,3,2-dioxaphosphorane (4.22 g, 1.0 equivalent) dissolved in tetrahydrofuran was added dropwise at 0° C. over about 1 hour. The mixture was further stirred at 0° C. for about 2 hours and at 45° C. for about 2 hours. After the reaction was completed, the precipitated triethylamine hydrochloride was removed by filtration to obtain an intermediate compound. This was used in the next reaction without purification.
[0069] Next, the obtained intermediate compound (1.0 equivalent) was placed in a four-neck flask, N,N,N',N'-tetramethyl-1,3-diaminopropane (1.0 equivalent) was dropped over 30 minutes, and the mixture was heated and refluxed for 24 hours in a mixed solvent of acetonitrile and tetrahydrofuran. After the reaction was completed, the solvent was removed by an evaporator, and the product was dissolved in a mixed solvent of chloroform:methanol:ammonia water (2:10:1, vol / vol / vol), and purified by column chromatography (inner diameter 50 mm, silica gel 280 g) filled with Wakosil (registered trademark) C-200. The solvent was distilled off under reduced pressure by an evaporator, and the title compound (compound 1) was obtained as a white solid (yield: 24.7%). 1 H NMR(D2O,DSS):δ 0.78-0.84(t,3H),1.22(m,18H),1.58-1.62(m,2H),1.90-2.12(m,2H),2.22(s,6H),2.41-2.50(m ,2H),3.16(s,6H),3.35-3.41(m,2H),3.61-3.65(m,2H),3.83-3.90(m,2H),4.22-4.25ppm(m,2H). ESI-MS:Calcd for [M+Na] + :473.635, Found:473.48. Elemental analysis: Calcd. for C 21 H 47 N2O4P·H2O:C,57.25;H,11.21;N,6.36. Found:C,57.75;H,11.36;N,6.45.
[0070] Synthesis Example 2: Synthesis of N,N-dimethyl-N-[(N',N'-dimethylamino)propyl]ammonium ethyl tetradecyl phosphate (Compound 2: C14PCAm) [ka] The title compound (Compound 2) was obtained (yield: 15.2%) by carrying out the same method as in Synthesis Example 1, except that 1-tetradecanol (1.0 equivalent) was used instead of 1-dodecanol (1.0 equivalent). 1 H NMR(D2O,DSS):δ 0.82-0.90(t,3H),1.23(m,22H),1.58-1.62(m,2H),1.92-2.10(m,2H),2.28(s,6H),2.41-2.50(m ,2H),3.19(s,6H),3.40-3.50(m,2H),3.62-3.70(m,2H),3.81-3.90(m,2H),4.20-4.30ppm(m,2H). ESI-MS:Calcd for [M+Na] + :445.58, Found:445.42. Elemental analysis: Calcd. for C 23 H 51 N2O4P·H2O:C,58.95;H,11.40;N,5.98. Found:C,59.89;H,11.68;N,5.99.
[0071] Synthesis Example 3: Synthesis of N,N-dimethyl-N-dodecyl-3-[N',N'-dimethyl-2-(dodecylphosphate)ethylammonium]propylammonium bromide (Compound 3: 2C12PCAm) [ka] 1-Bromododecane (5.56 g, 3.0 equivalents) was added to compound 1 (5.00 g, 1.0 equivalents) obtained in the above synthesis example 1, and the mixture was heated and refluxed in acetonitrile solvent for 6 hours. After the reaction was completed, the solvent was removed using an evaporator, and the mixture was washed with hexane, ethyl acetate, and acetone. The residue was put into chloroform, and insoluble matter was removed by filtration. The chloroform in the filtrate was removed using an evaporator, and the title compound (compound 3) was obtained as a white solid (total yield including the synthesis of compound 1: 1.9%). 1 H NMR(CDCl3,TMS):δ 0.85-0.88(t,6H),1.23(m,36H),1.59-1.70(m,2H),1.70-1.75(m,2H),2.70-2.90(m,2H),3.34(s,6H),3.4 5(s,6H),3.78-3.82(m,4H),3.84-3.90(m,2H),4.01-4.10(m,2H),4.20-4.30(m,2H),4.48-4.53ppm(m,2H). ESI-MS:Calcd for [M+Na] + :591.92, Found:591.57. Elemental analysis: Calcd. for C 33 H 72 N2O4PBr·H2O:C,57.46;H,10.81;N,4.06. Found:C,57.24;H,11.09;N,3.75.
[0072] Synthesis Example 4: Synthesis of N,N-dimethyl-N-tetradecyl-3-[N',N'-dimethyl-2-(tetradecylphosphate)ethylammonium]propylammonium bromide (Compound 4: 2C14PCAm) [ka] The title compound (compound 4) was obtained by carrying out the same method as in Synthesis Example 3, except that compound 2 (1.0 equivalent) was used instead of compound 1 (1.0 equivalent) and 1-bromotetradecane (3.0 equivalent) was used instead of 1-bromododecane (3.0 equivalent). (Total yield including the synthesis of compound 2: 4.2%) 1 H NMR(CDCl3,TMS):δ 0.85-0.90(t,6H),1.12(m,44H),1.50-1.63(m,2H),1.70-1.82(m,2H),2.68-2. 78(m,2H),3.35(s,6H),3.45(s,6H),3.70-3.98(m,10H),4.18-4.30ppm(m,2H). ESI-MS:Calcd for [M+Na] + :648.03, Found:647.69. Elemental analysis: Calcd. for C 37 H 80 N2O4PBr·2H2O:C,58.17;H,11.08;N,3.67. Found:C,58.40;H,10.82;N,3.91.
[0073] Test Example 1 Solubility Test The solubility in solvents (hydrophilic solvents) was examined for compounds 1 to 4. Purified water, ethanol, isopropyl alcohol, 1,3-butylene glycol, propylene glycol, dipropylene glycol, and glycerin were used as the solvents. 5 g of each solvent was mixed with 0.1 g of each compound or phospholipid (phosphatidylcholine) at 25°C and 70°C, and the solubility at each temperature was visually evaluated according to the following criteria. ◎: Uniformly dissolved 〇: Slight turbidity is observed △: Some insoluble matter ×: Insoluble matter present
[0074] The results are shown in Table 1 (Table 1-1 and Table 1-2). [Table 1]
[0075] As shown in the above table, compounds 1 to 4 exhibited high solubility in the solvent, whereas phosphatidylcholine exhibited low solubility.
[0076] Formulation Example 1 Cosmetics (Production Examples 1-1 to 1-6) (lotions) were produced having the compositions (formulations) shown in Table 2. Component A is a surfactant, Component D is a water-based component, and Component C is the other component. [Table 2]
[0077] Manufacturing method 1. Component C and 1,3-butylene glycol were mixed, and a portion of heated purified water was added to obtain a swollen product. 2. The remaining component D was added to component A and mixed to obtain a solution. 3. The above 1 was added to the above 2 to obtain a cosmetic preparation (lotion).
[0078] evaluation Solubility of component A: Solubility in component D (25°C) The solubility of component A in component D of each preparation was visually confirmed and evaluated according to the following criteria. ◎: Uniformly dissolved 〇: Slight turbidity is observed △: Some insoluble matter ×: Insoluble matter present
[0079] Feels good on the skin A test was conducted for each formulation by a panel of 20 experts, who rated it on a four-level scale using the absolute criteria below. The average score of all the panelists was calculated and judged according to the following criteria. Specifically, an appropriate amount of each preparation was applied to the skin, and the compatibility of the cosmetic with the skin upon application was evaluated. (Absolute Standard) 3: Very sensitive 2: Feel 1: Somewhat 0: No feeling (Judgment criteria) ◎: 2.5 points or more ○: 2 points or more and less than 2.5 points △: 1 point or more but less than 2 points ×: Less than 1 point
[0080] Moisturizing sensation 5 hours after application A test was conducted for each formulation by a panel of 20 experts, who rated it on a four-level scale using the absolute criteria below. The average score of all the panelists was calculated and judged according to the following criteria. Specifically, an appropriate amount of each example product was applied to the skin, and the moist feeling was evaluated 5 hours after application. (Absolute Standard) 3: Very sensitive 2: Feel 1: Somewhat 0: No feeling (Judgment criteria) ◎: 2.5 points or more ○: 2 points or more and less than 2.5 points △: 1 point or more but less than 2 points ×: Less than 1 point
[0081] As shown in Table 2, Formulation Examples 1-1 to 1-4 were excellent in solubility of component A, compatibility with the skin, and moisturizing feeling 5 hours after application. Therefore, it was suggested that Compounds 1 to 4 have high surface activity. On the other hand, Formulation Example 1-5 (without component A) and Formulation Example 1-6 (containing phosphatidylcholine) were not evaluated well.
[0082] Formulation Example 2 Cosmetics (Production Examples 2-1 to 2-6) (lotions) were produced having the compositions (formulations) shown in Table 3. Component A is a surfactant, Component B is an oil-based component, Component D is a water-based component, and Component C is the other component. [Table 3]
[0083] Manufacturing method 1. (Acrylates / alkyl acrylate (C10-30)) Crosspolymer and a portion of 1,3-butylene glycol were mixed, and a portion of heated purified water was added to obtain a swollen product. 2. The remaining component D was added to component A and mixed to obtain a solution. 3. To the above 2 was added the above 1 and the remaining component C (sodium hydroxide) to obtain an aqueous mixture. 4. The above 3 was heated to 75°C, and component B, which had been heated and mixed at 75°C, was added thereto and emulsified. After cooling, a cosmetic preparation (lotion) was obtained.
[0084] evaluation Solubility of component A: Solubility in component D (25°C) The solubility of component A in component D of each preparation was visually confirmed and evaluated in the same manner as in the evaluation of Preparation Example 1.
[0085] Feels good on the skin Using the same method as in the evaluation of Formulation Example 1, a use test was conducted for each formulation by a panel of 20 experts to evaluate its compatibility with the skin.
[0086] Moisturizing sensation 5 hours after application Using the same method as in the evaluation of Formulation Example 1, a test was conducted for each formulation by a panel of 20 experts, and the moist feeling was evaluated 5 hours after application.
[0087] As shown in Table 3, Formulation Examples 2-1 to 2-4 were excellent in solubility of Component A, skin compatibility, and moisturizing feeling 5 hours after application. Therefore, it was suggested that Compounds 1 to 4 have high surface activity (especially emulsifying ability). On the other hand, Formulation Example 2-5 (without Component A) and Formulation Example 2-6 (containing phosphatidylcholine) were not evaluated well.
[0088] Formulation Example 3 Cosmetics (Production Examples 3-1 to 3-6) (powder-containing oil-in-water emulsion (base)) were produced with the composition (formulation) shown in Table 4. Component A is a surfactant, component B is an oil-based component, component D is a water-based component, and component C is the other component. [Table 4] (Note) *1:SIMULGEL EG QD (SEPPIC SA)
[0089] Manufacturing method 1. Xanthan gum, (acrylates / alkyl acrylate (C10-30)) crosspolymer, and a portion of 1,3-butylene glycol were mixed, and a portion of heated purified water was added to obtain a swollen product. 2. The powder of component C, polysorbate 80, and a portion of 1,3-butylene glycol were added to obtain a dispersion. 3. The remaining component D was added to component A and mixed to obtain a solution. 4. To the above 3, the above 1, a mixture of (sodium acrylate / sodium acryloyldimethyltaurate) copolymer, isohexadecane, polysorbate 80, water, and triethanolamine were added to obtain an aqueous mixture. 5. The above 4 was heated to 75°C, and component B heated and mixed at 75°C was added thereto and emulsified. After cooling, an emulsion was obtained. 6. Add 2 above to 5 above and mix to obtain a powder-containing oil-in-water emulsion (base).
[0090] evaluation Solubility of component A: Solubility in component D (25°C) The solubility of component A in component D of each preparation was visually confirmed and evaluated in the same manner as in the evaluation of Preparation Example 1.
[0091] Feels good on the skin Using the same method as in the evaluation of Formulation Example 1, a use test was conducted for each formulation by a panel of 20 experts to evaluate its compatibility with the skin.
[0092] Moisturizing sensation 5 hours after application Using the same method as in the evaluation of Formulation Example 1, a test was conducted for each formulation by a panel of 20 experts, and the moist feeling was evaluated 5 hours after application.
[0093] As shown in Table 4, Formulation Examples 3-1 to 3-4 were excellent in solubility of component A, compatibility with the skin, and moisturizing sensation 5 hours after application. Therefore, it was suggested that Compounds 1 to 4 have high surface activity (especially emulsifying ability and dispersing ability). On the other hand, Formulation Example 3-5 (without component A) and Formulation Example 3-6 (containing phosphatidylcholine) were not evaluated well.
Claims
1. Formula (I): 【Chemistry 1】 [In the formula, R １ is a hydrocarbon group having 10 to 22 carbon atoms, R ２ is C １－６ is an alkyl group, R ３ is C １－６ is an alkyl group, R ４ is -NR ５ R ６ , or -N ＋ R ５ R ６ R ７ ・X － and R ５ is C １－６ is an alkyl group, R ６ is C １－６ is an alkyl group, R ７ is a hydrocarbon group having 10 to 22 carbon atoms, X － is an anion, and n is an integer from 2 to 30. A compound represented by the formula (I) or a salt thereof.
2. R １ The compound according to claim 1 , or a salt thereof, wherein is a linear or branched alkyl group.
3. R １ is a linear alkyl group having 10 to 16 carbon atoms, or a salt thereof.
4. 2. The compound according to claim 1, or a salt thereof, wherein n is an integer of 3 to 20.
5. R ２ is a methyl group, and R ３ is a methyl group, and R ５ is a methyl group, and R ６ The compound according to claim 1 , or a salt thereof, wherein is a methyl group.
6. R ７ The compound according to claim 1 , or a salt thereof, wherein is a linear or branched alkyl group.
7. R ７ is a linear alkyl group having 10 to 16 carbon atoms, or a salt thereof.
8. X － The compound according to claim 1 , or a salt thereof, wherein is a halide ion.
9. the below described: 【Chemistry 2】 2. The compound of claim 1, or a salt thereof, selected from the group consisting of:
10. A surfactant comprising the compound or salt thereof according to any one of claims 1 to 9.
11. A cosmetic comprising the compound or salt thereof according to any one of claims 1 to 9.
12. Use of the compound or salt thereof according to any one of claims 1 to 9 for producing a cosmetic preparation.
13. A method for producing the compound or salt thereof according to any one of claims 1 to 9, comprising: reacting a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (Ia): 【Transformation 3】 [In the formula, R １ , R ２ , R ３ , R ５ , R ６ , and n is as defined in claim 1. A manufacturing method comprising:
14. The compound of formula (Ia) is reacted with R ７ -Xa to obtain a compound of formula (Ib-1): 【Chemistry 4】 [In the formula, R １ , R ２ , R ３ , R ５ , R ６ , R ７ and n are as defined in claim 1, and Xa is a halogen atom. The method of claim 13 further comprising: