JP6940064B2 - Liquid crystal display of spicrysporic acid or its derivative, its manufacturing method - Google Patents

Description

The present invention relates to a liquid crystal display formed from spicrysporic acid or a derivative thereof or a salt thereof, and its utilization.

Spikrisporic acid is a natural polyvalent carboxylic acid obtained by fermentation, and various uses have been proposed due to its properties such as many reaction sites and low skin irritation. In addition, derivatization thereof has also been attempted (Patent Document 1).

Japanese Unexamined Patent Publication No. 08-198864

The present inventors have unexpectedly found that a liquid crystal can be formed by combining a specific spicrysporic acid derivative or a salt thereof with a specific solvent. The liquid crystal formed in this way can be used for various purposes, and is particularly useful for applications such as cosmetics and microstructure control.

またはその誘導体あるいはその塩と、溶媒とを含む液晶。
（項目２）
前記スピクリスポール酸またはその誘導体あるいはその塩が、開環スピクリスポール酸

の塩である、項目１に記載の液晶。
（項目３）
前記溶媒がアルコールを含む、項目１または２に記載の液晶。
（項目４）
前記アルコールが、１，３−ブタンジオール、１−オクタノール、エチレングリコール、ポリエチレングリコール、プロピレングリコール、ポリプロピレングリコール、グリセリン、ポリグリセリン、１，２−ヘキサンジオール、１，２−ペンタンジオール、３−メチル−１，３−ブタンジオール、エリスリトール、ソルビトール、キシリトールおよびそれらの組み合わせからなる群から選択される、項目３に記載の液晶。
（項目５）
前記溶媒が、１，３−ブタンジオールまたは１−オクタノールを含む、項目３に記載の液晶。
（項目６）
リオトロピック液晶である、項目１〜５のいずれか１項に記載の液晶。
（項目７）
ヘキサゴナル液晶またはラメラ液晶である、項目６に記載の液晶。
（項目８）
項目１〜７のいずれか１項に記載の液晶を含む化粧品。
（項目９）
前記スピクリスポール酸またはその誘導体あるいはその塩が、開環スピクリスポール酸

の塩である、項目８に記載の化粧品。
（項目１０）
前記開環スピクリスポール酸の塩が、１分子の開環スピクリスポール酸に対して１分子の陽イオン種が組み合わされた塩である、項目９記載の化粧品。
（項目１１）
前記液晶がラメラ液晶である、項目８〜１０のいずれか１項に記載の化粧品。
（項目１２）
項目１〜７のいずれか１項に記載の液晶の製造方法であって、
前記スピクリスポール酸またはその誘導体あるいはその塩と、前記溶媒とを混合して液晶を形成させる工程を含む製造方法。
（項目１３）
多孔質材料の製造方法であって、
スピクリスポール酸

またはその誘導体あるいはその塩と、溶媒とを含む組成物を提供する工程、および
該組成物中で多孔質材料を調製する工程
を含む製造方法。
（項目１４）
前記スピクリスポール酸またはその誘導体あるいはその塩が、開環スピクリスポール酸

の塩である、項目１３に記載の製造方法。
（項目１５）
多孔質材料の製造方法であって、
項目１〜７のいずれか１項に記載の液晶を提供する工程、および
形成された液晶を鋳型として多孔質材料を調製する工程
を含む製造方法。
（項目１６）
前記液晶がヘキサゴナル液晶である、項目１３〜１５のいずれか１項に記載の製造方法。
（項目１７）
前記多孔質材料がメソポーラスシリカである、項目１３〜１６のいずれか１項に記載の製造方法。
（項目１８）
項目１３〜１７のいずれか１項に記載の製造方法によって製造された多孔質材料。 Therefore, the present invention provides the following.
(Item 1)
Spicrisporic acid

Or a liquid crystal display containing a derivative thereof or a salt thereof and a solvent.
(Item 2)
The ring-opening spicrysporic acid is the spicysporic acid or a derivative thereof or a salt thereof.

The liquid crystal display according to item 1, which is a salt of the above.
(Item 3)
The liquid crystal display according to item 1 or 2, wherein the solvent contains alcohol.
(Item 4)
The alcohol is 1,3-butanediol, 1-octanol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, glycerin, polyglycerin, 1,2-hexanediol, 1,2-pentanediol, 3-methyl-. The liquid crystal according to item 3, which is selected from the group consisting of 1,3-butanediol, erythritol, sorbitol, xylitol and combinations thereof.
(Item 5)
The liquid crystal display according to item 3, wherein the solvent contains 1,3-butanediol or 1-octanol.
(Item 6)
The liquid crystal according to any one of items 1 to 5, which is a lyotropic liquid crystal.
(Item 7)
The liquid crystal according to item 6, which is a hexagonal liquid crystal or a lamellar liquid crystal.
(Item 8)
The cosmetic containing the liquid crystal according to any one of items 1 to 7.
(Item 9)
The ring-opening spicrysporic acid is the spicysporic acid or a derivative thereof or a salt thereof.

The cosmetic product according to item 8, which is a salt of.
(Item 10)
Item 9. The cosmetic product according to Item 9, wherein the salt of the ring-opening spicrysporic acid is a salt in which one molecule of the ring-opening spicysporic acid is combined with one molecule of a cationic species.
(Item 11)
The cosmetic product according to any one of items 8 to 10, wherein the liquid crystal is a lamellar liquid crystal.
(Item 12)
The method for manufacturing a liquid crystal according to any one of items 1 to 7.
A production method comprising a step of mixing the above-mentioned spicrysporic acid or a derivative thereof or a salt thereof with the above-mentioned solvent to form a liquid crystal display.
(Item 13)
It is a method for manufacturing a porous material.
Spicrisporic acid

A production method comprising a step of providing a composition containing the derivative or a salt thereof and a solvent, and a step of preparing a porous material in the composition.
(Item 14)
The ring-opening spicrysporic acid is the spicysporic acid or a derivative thereof or a salt thereof.

The production method according to item 13, which is a salt of the above.
(Item 15)
It is a method for manufacturing a porous material.
A production method comprising the step of providing the liquid crystal according to any one of items 1 to 7 and the step of preparing a porous material using the formed liquid crystal as a template.
(Item 16)
The production method according to any one of items 13 to 15, wherein the liquid crystal is a hexagonal liquid crystal.
(Item 17)
The production method according to any one of items 13 to 16, wherein the porous material is mesoporous silica.
(Item 18)
A porous material produced by the production method according to any one of items 13 to 17.

In the present invention, it is intended that the one or more features described above may be provided in combination in addition to the specified combinations. Further embodiments and advantages of the present invention will be recognized by those skilled in the art upon reading and understanding the following detailed description, if necessary.

The present invention provides a liquid crystal display formed from spicrysporic acid or a derivative thereof or a salt thereof, thereby providing a novel material useful for use in cosmetics, fine structure control, and the like.

FIG. 1 shows the critical micelle concentration (CMC) of spicrysporic acid or a derivative thereof or a salt thereof and the surface tension value (γ _CMC ) at CMC. It also shows the ability to capture Ca by chelation. FIG. 2 shows the particle size of micelles formed by the trisodium salt (O-3Na) of ring-opened spicrysporic acid. The horizontal axis represents the particle size of micelles in a logarithm, and the vertical axis represents the number of micelle particles of each particle size when the number of formed micelle particles is 100%. The particle size of micelles of O-3Na was 3.4 ± 0.4 nm. FIG. 3 shows the success or failure of liquid crystal formation when only O-3Na and water are used, or when glycerin, 1,3-butanediol or sorbitol is further added to O-3Na and water. A liquid crystal (hexagonal liquid crystal) was formed only in the solution to which 1,3-butanediol was added. The lower photograph is an image taken by a polarizing microscope (OLYMPUS BX41), and the scale bar represents 60 μm. FIG. 4 shows the ability to form a lyotropic liquid crystal in a three-component system of O-3Na, water and 1,3-butanediol (1,3-BG). The photograph is an image taken by a polarizing microscope (OLYMPUS BX41) in the composition of O-3Na: water: 1,3-butanediol (w / w) = 53: 35: 12 (top) and 46: 46: 8 (bottom). Yes, the scale bar represents 60 μm. A fan-shaped texture peculiar to hexagonal liquid crystal was observed. FIG. 5 shows an image of a liquid crystal display formed in a three-component system of O-3Na, water, and 1-octanol. It is an image by a polarizing microscope (OLYMPUS BX41) in the composition of O-3Na: water: 1-octanol (w / w) = 65: 28: 7, and the scale bar represents 60 μm. A mosaic-like texture peculiar to lamellar liquid crystal was observed. FIG. 6 is a schematic diagram of the synthesis of mesoporous silica (MS). FIG. 7 shows a performance evaluation of mesoporous silica (MS) obtained by using a trisodium salt (O-3Na) of ring-opened spicrysporic acid as a template. The nitrogen adsorption isotherms of the mesoporous silica obtained by using O-3Na as a template, the mesoporous silica obtained by using sodium dodecyl sulfate (SDS) as a template, and the mesoporous silica of SBA-15 are shown. The filled circles indicate the adsorption isotherms, and the white circles indicate the desorption isotherms. FIG. 8 shows SEM images (top) and TEM images (bottom) of mesoporous silica (MS) obtained by using a trisodium salt (O-3Na) of ring-opened spicrysporic acid as a template, and O acid and O acid at pH = 10. Shows the chemical state of the silica skeleton. The scale bar represents 100 nm.

Hereinafter, the present invention will be described while showing the best mode. Throughout the specification, it should be understood that the singular representation also includes its plural concept, unless otherwise stated. Therefore, it should be understood that singular articles (eg, "a", "an", "the", etc. in English) also include the plural concept unless otherwise noted. It should also be understood that the terms used herein are used in the meaning commonly used in the art unless otherwise noted. Thus, unless otherwise defined, all terminology and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, this specification (including definitions) takes precedence.

(Definition)
The definitions and / or basic technical contents of terms particularly used in the present specification will be described below as appropriate.

As used herein, the term "cationic species" refers to a molecule that is mostly present as a cation when present at a dilute concentration in water at pH = 7 at normal temperature and pressure, or a molecule containing a cationic moiety (eg, for example. Refers to a molecule or atom that exists as an amino acid, etc.). For example, as cation species, Na (sodium), Mg (magnesium), NH ₃ (ammonia), CH ₂ (OH) CH ₂ NH ₂ (ethanolamine), and CH (COOH) (NH ₂ ) CH ₂ CH ₂ CH ₂ CH ₂ NH ₂ (lysine) can be mentioned, but is not limited thereto. In the present specification, regardless of whether the cation species is an atom or a molecule, it is counted as one molecule of cation species and two molecules of cation species.

（３Ｓ，４Ｓ）−３−ヒドロキシ−１，３，４−テトラデカントリカルボン酸１，３−ラクトン（Ｓ酸）
を有する天然の両親媒性化合物であり、糸状菌（Penisillium spiculisporum Lehman 10−1）から生産することができる。本明細書において、（３Ｓ，４Ｓ）−３−ヒドロキシ−１，３，４−テトラデカントリカルボン酸１，３−ラクトンおよびその塩を総称して、スピクリスポール酸またはＳ酸と呼ぶ。スピクリスポール酸は微生物由来の酵素反応によって生産され、分子内に少なくとも二つのキラル炭素を含み、複数の官能基を有することが特徴である。スピクリスポール酸は二価の酸であり、ｐＫａ_１は４．５１であり、ｐＫａ_２は６．８８である。１分子のスピクリスポール酸は、１分子の陽イオン種または２分子の陽イオン種とともに塩を形成し得る。本明細書において、「Ｓ−１Ｂ」および「Ｓ−２Ｂ」（Ｂは、Ｎａ（ナトリウム）などの陽イオン種を表す）と表記する場合、それぞれ、１分子のスピクリスポール酸に対して１分子の陽イオン種が組み合わされた塩、および１分子のスピクリスポール酸に対して２分子の陽イオン種が組み合わされた塩を表す。例えば、スピクリスポール酸の２ナトリウム塩は、「Ｓ−２Ｎａ」と表記される。ここで、陽イオン種Ｂは、常温常圧でｐＨ＝７の水中に薄い濃度で存在する場合に大部分が１価、２価またはそれより多くの価数の陽イオンとして存在する原子または分子であり得る。 Spikrisporic acid (also referred to herein as "S acid") has the following structure:

(3S, 4S) -3-Hydroxy-1,3,4-Tetradecane tricarboxylic acid 1,3-lactone (S acid)
It is a natural amphipathic compound having, and can be produced from a filamentous fungus (Penisillium spiculisporum Lehman 10-1). In the present specification, (3S, 4S) -3-hydroxy-1,3,4-tetradecantricarboxylic acid 1,3-lactone and salts thereof are collectively referred to as spicrysporic acid or S acid. Spicrisporic acid is produced by an enzymatic reaction derived from a microorganism, contains at least two chiral carbons in the molecule, and is characterized by having a plurality of functional groups. Spicrisporic acid is a divalent acid, pKa ₁ is 4.51 and pKa ₂ is 6.88. One molecule of spicrysporic acid can form a salt with one molecule of cation species or two molecules of cation species. In the present specification, when referred to as "S-1B" and "S-2B" (B represents a cationic species such as Na (sodium)), one molecule is used for one molecule of spicrysporic acid, respectively. Represents a salt in which two cation species are combined with each other, and a salt in which two molecules of cation species are combined with one molecule of spicrysporic acid. For example, the disodium salt of spicrysporic acid is written as "S-2Na". Here, the cation species B is an atom or molecule that is mostly present as cations having a valence of monovalent, divalent or higher when present at a low concentration in water at pH = 7 at normal temperature and pressure. Can be.

As used herein, the term "spicrysporic acid derivative" refers to a compound having a chemical structure similar to that of spicysporic acid. In one embodiment, the spicrysporic acid derivative can be a compound synthesized from spicysporic acid as a starting material.

（３Ｓ，４Ｓ）−３−ヒドロキシ−１，３，４−テトラデカントリカルボン酸
を有する天然の両親媒性化合物であり、スピクリスポール酸誘導体の１種である。本明細書において、（３Ｓ，４Ｓ）−３−ヒドロキシ−１，３，４−テトラデカントリカルボン酸およびその塩を総称して、開環スピクリスポール酸またはＯ酸と呼ぶ。開環スピクリスポール酸は三価の酸であり、ｐＫａ_１は４．８６であり、ｐＫａ_２は６．５６であり、ｐＫａ_３は７．４４である。１分子の開環スピクリスポール酸は、１分子の陽イオン種、２分子の陽イオン種または３分子の陽イオン種とともに塩を形成し得る。本明細書において、「Ｏ−１Ｂ」、「Ｏ−２Ｂ」および「Ｏ−３Ｂ」（Ｂは、Ｎａ（ナトリウム）などの陽イオン種を表す）と表記する場合、それぞれ、１分子の開環スピクリスポール酸に対して１分子の陽イオン種が組み合わた塩、１分子の開環スピクリスポール酸に対して２分子の陽イオン種が組み合わた塩および１分子の開環スピクリスポール酸に対して３分子の陽イオン種が組み合わた塩を表す。例えば、開環スピクリスポール酸の３ナトリウム塩は、「Ｏ−３Ｎａ」と表記される。ここで、陽イオン種Ｂは、常温常圧でｐＨ＝７の水中に薄い濃度で存在する場合に大部分が１価、２価またはそれより多くの価数の陽イオンとして存在する原子または分子であり得る。 Ring-opening spicrysporic acid (open ring acid) (also referred to herein as "O acid") has the following structure:

(3S, 4S) A natural amphipathic compound having -3-hydroxy-1,3,4-tetradecantricarboxylic acid, which is one of the spicrysporic acid derivatives. In the present specification, (3S, 4S) -3-hydroxy-1,3,4-tetradecantricarboxylic acid and salts thereof are collectively referred to as ring-opening spicrysporic acid or O acid. Ring-opening spicrysporic acid is a trivalent acid, pKa ₁ is 4.86, pKa ₂ is 6.56, and pKa ₃ is 7.44. One molecule of ring-opening spiclisporic acid can form a salt with one molecule of cation species, two molecules of cation species or three molecules of cation species. In the present specification, when referred to as "O-1B", "O-2B" and "O-3B" (B represents a cation species such as Na (sodium)), one molecule is opened, respectively. For spicrysporic acid with one molecule of cationic species, for one molecule of ring-opening spicrysporic acid with two molecules of cationic species for salt and for one molecule of ring-opening spicrysporic acid Represents a salt in which three cation species are combined. For example, the trisodium salt of ring-opened spicrysporic acid is labeled "O-3Na". Here, the cation species B is an atom or molecule that is mostly present as cations having a valence of monovalent, divalent or higher when present at a low concentration in water at pH = 7 at normal temperature and pressure. Can be.

As used herein, the term "solvent" refers to any liquid in which a spicrysporic acid derivative or a salt thereof can be dispersed. Spikrisporic acid or a derivative thereof or a salt thereof mixed with a solvent may be dissolved, may form micelles, may form a liquid crystal display, or may be in an insoluble state such as suspension. It may be.

As used herein, the term "micelle" refers to an aggregate of amphipathic molecules formed in water. When micelles are formed in water, the lipophilic portion of the amphipathic molecule is oriented towards the inside of the aggregate and the polar hydrophilic portion is oriented towards the outside of the aggregate. Further, when excess oil is added to the micelles formed in water, an oil-in-water emulsion in which the oil is dispersed in water is formed.

As used herein, the term "liquid crystal" refers to the form of a substance in a state between the isotropic molecular order found in a typical liquid and the structured order of molecules found in a typical solid. In liquid crystals, molecular order is formed in liquids. In the liquid crystal display, spicrysporic acid or a derivative thereof is arranged so as to exhibit some molecular order. Some compound can be held in the space between the formed liquid crystal structures. It is known that a specific compound has a liquid crystal forming ability, but it has not been known that a liquid crystal can be formed from spicrysporic acid or a derivative thereof.

As used herein, the term "lyotropic liquid crystal" refers to a liquid crystal capable of causing a phase change from an isotropic phase to a liquid crystal phase (or vice versa) by changing the concentration of a component in a solvent.

In the present specification, the "hexagonal liquid crystal" refers to a liquid crystal having a molecular order of a honeycomb-like structure (hexagonal phase) in which a large number of hexagonal columns are arranged.

In the present specification, the "lamellar liquid crystal" or "Lα liquid crystal" is a bilayer film formed by orienting the hydrophilic portion of an amphipathic molecule outward and the hydrophobic portion inward. Refers to a liquid crystal having a phase having a molecular order (lamellar phase). The lamellar and hexagonal phases can be observed, for example, through a polarizing microscope.

As used herein, the term "cubic liquid crystal" refers to a liquid crystal having a molecular order in which micelles formed by amphipathic molecules are arranged in cubic crystals. Cubic liquid crystals are optically isotropic and cannot be observed through a polarizing microscope, but their formation can be confirmed by, for example, small-angle X-ray scattering or viscoelasticity measurement.

In the present specification, when "X% is a liquid crystal display" for a certain component, it means that X% of the components existing in the composition are involved in the formation of the liquid crystal structure.

As used herein, the term "cosmetics" is used to cleanse, beautify, enhance attractiveness, change the appearance of the body, or apply it to the body, spray it, or otherwise in a similar manner to keep the skin or hair healthy. Refers to any product intended to be used. In the present specification, the “cosmetics” is not limited to “cosmetics” under the so-called Pharmaceutical and Medical Devices Act (former Pharmaceutical Affairs Law), and may be, for example, quasi-drugs, pharmaceuticals, or miscellaneous goods.

As used herein, the term "mesoporous silica" refers to a porous material containing silicon dioxide (silica) as a main component and having uniform pores (mesopores) having an average diameter of 2 to 50 nm. Mesoporous silica is used as a catalyst, an adsorbent material, an optical device, a gas sensor, a separation membrane, and the like.

(Formation of liquid crystal display)
In one aspect, the present invention provides a liquid crystal display containing spicrysporic acid or a derivative thereof or a salt thereof, and a solvent. The inventors have found that it is possible to form a liquid crystal display by using a specific one of spicrysporic acid or a derivative thereof. In one embodiment, the liquid crystal can be a lyotropic liquid crystal. In one embodiment, the liquid crystal can be a hexagonal liquid crystal, a lamellar liquid crystal, a triangular columnar liquid crystal or a cubic liquid crystal. Even when the same spicrysporic acid derivative (for example, O acid) is used, the structure of the liquid crystal formed may be different depending on the form of the salt. The morphology of the liquid crystal can be confirmed, for example, by observing with a polarizing microscope.

In one aspect, the present invention provides a method for producing a liquid crystal display containing spicrysporic acid or a derivative thereof or a salt thereof, and a solvent. In one embodiment, the liquid crystal display of the present invention can be prepared by mixing spicrysporic acid or a derivative thereof or a salt thereof with a solvent, heating and stirring the mixture, and then allowing the mixture to stand. In one embodiment, the solvent can be mixed in various proportions with spicrysporic acid or a derivative thereof or a salt thereof. In one embodiment, the heating can be up to around 70 ° C. Any means can be used for stirring, for example, a vortex mixer or the like can be used. In one embodiment, heating, stirring and subsequent standing may be repeated multiple times.

で表される構造を有し、式中、
Ｒ^１、Ｒ^２およびＲ^３は、それぞれ独立に、−ＯＲ^Ａ、−ＮＨＲ^Ａまたは−Ｎ（Ｒ^Ａ）_２であり、
Ｒ^４は、Ｈまたは−ＯＲ^Ａであり、
ここで、Ｒ^Ａは、炭素数１〜２１の飽和又は不飽和である分岐または直鎖炭化水素基であり、例えば、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｎ−ペンチル、アリル、オクチル、４−オクテニル、２−オクテニル、２−エチルヘキシル、オレイル、パルミチル、ヘキシル、２−ヘキセニル、１１−ヘキサデセニル、ヘキサデシル、シクロヘキシル、ステアリル、またはゲラニルなどであるか、または
Ｒ^１、Ｒ^２、Ｒ^３およびＲ^４のうちのいずれか２つは、一緒になって環を形成していてもよく、ここで、Ｒ^１、Ｒ^２、Ｒ^３およびＲ^４のうちの環を形成した２つは、一緒になって−Ｏ−を形成する、あるいは、２つの分子におけるＲ^１、Ｒ^２、Ｒ^３およびＲ^４のうちのいずれか１つ同士が分子間で連結し、２量体を形成してもよい。 In one embodiment, the liquid crystal display of the present invention is formed from spicrysporic acid or a derivative thereof or a salt thereof. In one embodiment, the spicrysporic acid derivative used is the formula I below.

It has a structure represented by, and in the formula,
R ¹ , R ² and R ³ are independently -OR ^A , -NHR ^A or -N ( ^RA ) ₂ , respectively.
R ⁴ is H or -OR ^A,
Here, ^RA is a branched or linear hydrocarbon group having 1 to 21 carbon atoms, which is saturated or unsaturated, and is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl. , Allyl, octyl, 4-octenyl, 2-octenyl, 2-ethylhexyl, oleyl, palmityl, hexyl, 2-hexenyl, 11-hexadecenyl, hexadecyl, cyclohexyl, stearyl, or geranyl, or R ¹ , R ² , R ³ and R ⁴ may be combined to form a ring, where the ring of R ¹ , R ² , R ³ and R ⁴ is formed 2 One forms -O- together, or any one of R ¹ , R ² , R ³ and R ^{4 in} the two molecules is linked between the molecules to form a dimer. It may be formed.

の構造を有する開環スピクリスポール酸（Ｏ酸）である。１つの実施形態において、スピクリスポール酸またはその誘導体は塩の形態で使用される。スピクリスポール酸またはその誘導体の塩は、スピクリスポール酸またはその誘導体と、水酸化ナトリウム、水酸化カリウム、水酸化リチウム、水酸化マグネシウム、水酸化カルシウム、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、グアニジン、アルギニン、リシンおよびそれらの組み合わせから選択される塩基との組み合わせで形成される塩であり得る。スピクリスポール酸またはその誘導体の塩は、スピクリスポール酸またはその誘導体に対して、ナトリウム、カリウム、リチウム、マグネシウム、カルシウム、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、グアニジン、アルギニン、リシンおよびそれらの組み合わせから選択される陽イオン種が組み合わされた塩であり得る。１つの実施形態において、本発明の液晶は、開環スピクリスポール酸（Ｏ酸）と、水酸化ナトリウムとの組み合わせで形成される塩から形成される。 In one embodiment, the spicrysporic acid or derivative thereof used

It is a ring-opening spicrysporic acid (O acid) having the structure of. In one embodiment, spicrysporic acid or its derivatives are used in the form of salts. The salts of spicrysporic acid or its derivatives include sodium hydroxide, potassium hydroxide, lithium hydroxide, magnesium hydroxide, calcium hydroxide, monoethanolamine, diethanolamine, triethanolamine, guanidine, and spicrysporic acid or its derivatives. It can be a salt formed in combination with a base selected from arginine, lysine and combinations thereof. Salts of spicrysporic acid or its derivatives are derived from sodium, potassium, lithium, magnesium, calcium, monoethanolamine, diethanolamine, triethanolamine, guanidine, arginine, lysine and combinations thereof, relative to spicrysporic acid or its derivatives. It can be a combination salt of the selected cation species. In one embodiment, the liquid crystal display of the present invention is formed from a salt formed by a combination of ring-opening spicrysporic acid (O acid) and sodium hydroxide.

In one embodiment, the liquid crystal of the present invention is a salt (O-1B) in which one molecule of ring-opening spicrysporic acid (O acid) is combined with one molecule of a cation species, and two molecules of cations. It is formed from a salt with a combination of seeds (O-2B) or a salt with a combination of three molecules of cationic species (O-3B) (where B represents a cationic species). The number and / or valence of cationic species in the salt of spicrysporic acid or a derivative thereof can affect the morphology of the liquid crystal display. In one embodiment, the liquid crystal of the present invention is a lamellar liquid crystal formed from a salt (O-1B) in which one molecule of cation species is combined with one molecule of ring-opening spicrysporic acid. In one embodiment, the liquid crystal display of the present invention combines one molecule of ring-opening spicrysporic acid with a salt (O-2B) in which two molecules of cationic species are combined or three molecules of cationic species combined. It is a hexagonal liquid crystal formed from the salt (O-3B).

In one embodiment, the liquid crystals of the invention are formed in a solvent containing alcohol. If the solvent containing the alcohol (the type of solvent and / or the weight ratio of the composition) is not properly selected, it is possible that no liquid crystal will be formed or the desired liquid crystal will not be formed. In one embodiment, the alcohol-containing solvent comprises water. Examples of water include, but are not limited to, normal water, purified water, hard water, soft water, natural water, deep ocean water, electrolytic alkaline ionized water, electrolytically acidic ionized water, ionized water, and cluster water. In one embodiment, the alcohol is 1,3-butanediol, 1-octanol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, glycerin, polyglycerin, 1,2-hexanediol, 1,2-pentanediol. , 3-Methyl-1,3-butanediol, erythritol, sorbitol, xylitol and combinations thereof. When polymer alcohols such as polyethylene glycol, polypropylene glycol and polyglycerin are used in one embodiment, their number average molecular weight is 100 to 20000, preferably 200 to 2000, more preferably 400 to 1500.

In one embodiment, spicysporic acid or a derivative thereof or a salt thereof, water,
A liquid crystal display can be obtained from only the three components of alcohol and alcohol.

The liquid crystal display of the present invention may further contain a surfactant other than spicrysporic acid or a derivative thereof or a salt thereof. Further addition of a surfactant other than spicrysporic acid or a derivative thereof or a salt thereof may change the structure of the formed liquid crystal. As such a surfactant, an appropriate one can be arbitrarily selected depending on the application such as microstructure control of cosmetics and materials. For example, as the surfactant, a fatty acid sequel (sodium laurate, palmitic acid) can be selected. (Sodium, etc.), anionic surfactants such as potassium lauryl sulfate, triethanolamine ether alkylsulfate, cationic surfactants such as stearyltrimethylammonium chloride, benzalconium chloride, and laurylamine oxide, betaine-based surfactants. (Alkylbetaine, amide betaine, sulfobetaine, etc.), imidazoline-based amphoteric surfactant (2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyroxy disodium salt, etc.), amphoteric surfactant such as acylmethyltaurine Agents, polyethylene glycol fatty acid esters (polyethylene glycol monooleate, polyethylene glycol monostearate, polyethylene glycol monolaurate, etc.), sorbitan fatty acid esters (sorbitan monooleate, sorbitan monostearate, sorbitan monoisostearate, sorbitan monolaurate, etc.) , Sesquioleate sorbitan, etc.), Monoglycerin fatty acids (glycerin laurate, glycerin myristate, glycerin stearate, glycerin behenate, glycerin oleate, glycerin isostearate, coconut oil fatty acid glycerin, hardened beef oil fatty acid glycerin, lanophosphate Glycerin, etc.), Polyglycerin fatty acids (diglyceryl stearate, diglyceryl oleate, diglyceryl isostearate, tetraglyceryl stearate, tetraglyceryl oleate, hexaglyceryl laurate, decaglyceryl stearate, etc.), propylene glycol fatty acid ester Classes (propylene glycol monostearate, etc.), cured castor oil derivatives, glycerin alkyl ethers, POE sorbitan fatty acid esters (polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, monooleine) Polyoxyethylene sorbitan acid, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan triisostearate, etc.), POE sorbit fatty acid esters (POE-sorbit monolaurate, etc.) , POE glycerin fatty acid esters (polyoxyethylene glyceryl monomyristate, polyoxyethylene glyceryl monostearate, polyoxyethylene glyceryl monoisostearate, polyoxyethylene glyceryl triisostearate, etc.), POE fatty acid esters (POE monooleate, POE, etc.) Distearate, etc.), POE alkyl ethers (polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene behenyl ether, polyoxyethylene oleyl ether, polyoxyethylene hexyl decyl ether, polyoxyethylene iso) Stearyl ether, polyoxyethylene octyldodecyl ether, polyoxyethylene decylpentadecyl ether, polyoxyethylene decyltetradecyl ether, polyoxyethylene cholesteryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene poly Oxypropylene cetyl ether, polyoxyethylene polyoxypropylene decyl tetradecyl ether, etc.), POE alkylphenyl ethers (POE nonylphenyl ether, etc.), polyoxyethylene fatty acid amide (lauric acid diethanolamide, coconut oil fatty acid diethanolamide, polyoxy) Ethylene stearate amide, etc.), Pluronic type, POE / POP alkyl ethers (POE / POP2-decyltetradecyl ether, etc.), Tetronics, POE castor oil / hardened castor oil derivative (POE castor oil, POE cured castor oil, etc.) Etc.), sucrose fatty acid ester, alkyl glucoside, polyoxyethylene sorbit honey wax, polyoxyethylene lanolin, polyoxyethylene lanolin alcohol, polyoxyethylene sorbitol lanolin, nonionic surfactants such as dimethyllaurylamine oxide, etc. Be done.

The liquid crystal of the present invention may further contain at least one selected from oily components, various active ingredients, thickeners, powders, ultraviolet absorbers, organically modified clay minerals and the like.

In one embodiment, the liquid crystal of the present invention is in a solvent containing 0.02-70% by weight, preferably 27-70% by weight, more preferably 43-63% by weight of spicrysporic acid or a derivative thereof or a salt thereof. Is formed by. In one embodiment, the liquid crystal display of the present invention is formed in a solvent containing 5 to 46% by weight, preferably 7 to 46% by weight, more preferably 8 to 30% by weight of water. In one embodiment, the liquid crystals of the invention are formed in a solvent containing 9-55% by weight, preferably 9-29% by weight, more preferably 14-22% by weight of alcohol. In one embodiment, the weight ratio of the composition of the salt, water and alcohol of spicrysporic acid or a derivative thereof preferred for forming the liquid crystal is ring-opening spicysporate: water: (1,3-butanediol or 1). -Octanol) = 53: 36: 11-47: 31: 22. In one embodiment, the preferred combination of spicrysporic acid or derivatives thereof, water and alcohol for forming hexagonal liquid crystals is ring-opening spicrysporate, water and 1,3-butanediol or 1-octanol. Although not bound by theory, the addition of alkanediols such as 1,3-butanediol improves the hydrophilicity of spicrysporic acid or its derivatives or salts thereof, making them more compatible with water. It is thought to promote the formation of liquid crystals.

In one embodiment, when a liquid crystal is formed from spicrysporic acid or a derivative thereof or a salt thereof, the component can be supported in the formed liquid crystal by adding another component. Any component to be supported on the liquid crystal can be selected according to the purpose. For example, a surfactant, an oil component, various active ingredients, a thickener, a powder, an ultraviolet absorber, and an organically modified clay mineral. And so on.

(Use of LCD)
In one aspect, the present invention provides a composition comprising a liquid crystal formed from spicrysporic acid or a derivative thereof or a salt thereof. The composition can be used in any application suitable for the liquid crystals of the present invention. In one embodiment, the composition can be a composition for cosmetics. In one embodiment, the composition can be a composition for controlling the microstructure of the material. In one embodiment, the composition can be a composition for the preparation of porous materials.

In one embodiment, the compositions of the present invention for cosmetics contain 0.02-70% by weight, preferably 27-70% by weight, more preferably 43-63% by weight of a spicrysporic acid derivative or salt thereof. include. The liquid crystal-forming spicrysporic acid or a derivative thereof or a salt thereof can maintain the liquid crystal state even after being added to the composition. In one embodiment, the composition of the present invention for cosmetics comprises a hexagonal liquid crystal or lamellar liquid crystal, preferably a lamellar liquid crystal, formed from spicrysporic acid or a derivative thereof or a salt thereof. By making the liquid crystal structure of the lyotropic liquid crystal a lamellar structure, it can be approximated to the structure formed by the intercellular lipids of the human stratum corneum. By making the liquid crystal structure of the lyotropic liquid crystal into a lamellar structure in this way, the affinity for the structure of the intercellular lipid is increased, and the components retained in the liquid crystal can be easily adapted to the skin.

In one embodiment, the spicrysporic acid derivative or salt thereof contained in the composition of the present invention for cosmetics is 0.02 to 70% by weight, preferably 27 to 70% by weight, more preferably 43 to 63. Weight% is liquid crystal.

The composition of the present invention for cosmetics may be in any form suitable for the liquid crystal of the present invention, and may be, for example, oil-in-water (O / W) type, water-in-oil (W / O) type, W / Emulsified cosmetics such as O / W type and O / W / O type, oil-based cosmetics, solid cosmetics, liquid cosmetics, paste-like cosmetics, stick-like cosmetics, volatile oil-type cosmetics, powder-like cosmetics, jelly-like cosmetics, gel-like Examples thereof include cosmetics, paste-like cosmetics, emulsified polymer-type cosmetics, sheet-like cosmetics, mist-like cosmetics, spray-type cosmetics, and aerosol-type cosmetics.

The compositions of the present invention for cosmetics can be used in any application suitable for the liquid crystal of the present invention, for example, cleaning cosmetics, hair cosmetics, basic cosmetics, make-up cosmetics, aromatic cosmetics, tans and tans. It can be used as a stop cosmetic, lip cosmetic or bath salt.

The composition of the present invention for cosmetics may be added with any ingredient or additive usually used in cosmetics, for example, an oily base, a moisturizer, a surfactant, a thickener, a solvent / jet. Agents, antioxidants, reducing agents, oxidizing agents, preservatives, chelating agents, pH regulators, powders, inorganic salts, UV absorbers, vitamins, anti-inflammatory agents, blood circulation promoters, hormones, anti-wrinkle agents , Anti-aging agents, tightening agents, cold sensation agents, warming agents, wound healing promoters, irritation palliatives, painkillers, cell activators, plant / animal / microbial extracts, antipruritic agents, keratin exfoliating / dissolving agents, Sweat agents, refreshing agents, astringents, enzymes, nucleic acids, fragrances, pigments / colorants / dyes / pigments and the like may be added.

In one embodiment, the composition of the present invention for controlling the microstructure of a material comprises 0.02-70% by weight, preferably 0.02-63% by weight, of spicrysporic acid or a derivative thereof or a salt thereof. More preferably, it contains 0.02 to 50% by weight. The liquid crystal-forming spicrysporic acid or a derivative thereof or a salt thereof can maintain the liquid crystal state even after being added to the composition.

The compositions of the present invention for controlling the microstructure of materials can be used in any application suitable for the liquid crystals of the present invention, such as base materials for cosmetics and pharmaceuticals, templates for the preparation of porous materials, etc. It can be used as a liquid crystal emulsification method, an electronic material, a specific reaction field, and the like. In one embodiment, the porous material is mesoporous silica (MS). In one embodiment, the preferred liquid crystal for the production of the porous material may be a hexagonal liquid crystal having a honeycomb-like honeycomb structure. This is because the surface area (specific surface area) per unit volume of the formed porous material is large and the adsorption amount is large.

In one aspect, the present invention is a method for producing a porous material, wherein a step of providing a composition containing spicrysporic acid or a derivative thereof or a salt thereof and a solvent, and the porous material in the composition. Provided is a manufacturing method including a step of preparing. In one embodiment, the present invention is a method for producing a porous material, wherein a step of providing a liquid crystal containing spicrysporic acid or a derivative thereof or a salt thereof and a solvent, and the formed liquid crystal as a template are porous. Provided is a manufacturing method including a step of preparing a material. In one embodiment, liquid crystals can be obtained from only three components, spicrysporic acid or its derivatives or salts thereof, water, and alcohols, and porous materials can be prepared without the use of petroleum-derived synthetic surfactants.

As used herein, "or" is used when "at least one" of the matters listed in the text can be adopted. The same applies to "or". When "within a range" of "two values" is specified in the present specification, the range also includes the two values themselves.

References such as scientific literature, patents, and patent applications cited herein are incorporated herein by reference in their entirety to the same extent as each specifically described.

The present invention has been described above with reference to preferred embodiments for ease of understanding. Hereinafter, the present invention will be described based on examples, but the above description and the following examples are provided for purposes of illustration only and not for the purpose of limiting the present invention. Therefore, the scope of the present invention is not limited to the embodiments or examples specifically described in the present specification, but is limited only by the claims.

Examples are described below.
(Example 1)
Synthesis of trisodium salt (O-3Na) of ring-opened spicrysporic acid

Weigh 10 g of spicrysporic acid (S acid) (Iwata Kagaku, Shizuoka, Japan) in a eggplant flask, add 15 ml of water and 35 ml of 3N NaOH aqueous solution (3.2 equal to S acid) to dissolve, and dissolve. The mixture was refluxed at 100 ° C. for 2 hours. By performing an evaporator and freeze-drying treatment, a trisodium salt (O-3Na) of ring-opening spicrysporic acid was obtained.

Various NMR (Bruker AVANCE 400) (Bruker Biospin, Kanagawa, Japan) measurements were performed to identify the resulting products. 30 mg of the product was dissolved in 0.6 ml of heavy water, and 2 μl of 1,4-dioxane was added as an internal standard substance. ^{When 1} H-NMR (400 MHz) and ¹³ C-NMR (100 MHz) were measured for this solution, the following spectra were obtained.

^{1 1} H-NMR (400 MHz) spectrum: δ (ppm) = 2.54 (dd, J = 4.0, 12.0 Hz, 1H, CHOONa, d), 2.27 (m, 1H, CH ₂ , f) , 1.96 (m, 2H, CH ₂ , e and f), 1.66 (m, 2H, CH ₂ , can and e), 1.23, (17H, -CH _2- , band c), 0.82 (t, J = 6.5Hz). (The peak of water was used as a reference (δ = 4.79)).

¹³ C-NMR (100 MHz) spectrum: δ (ppm) = 184.8 (C = O, g), 184.3 (C = O, i), 181.9 (C = O, h), 80.9 (C, j), 57.0 (CH, d), 37.1 (CH ₂ , e), 34.4 (CH ₂ , f), 32.8 (CH ₂ ), 30.4 (CH ₂ ) , 30.3 (2C, CH ₂ ), 30.1 (2C, CH ₂ ), 29.6 (CH ₂ ), 28.9 (CH ₂ ), 23.6 (CH ₂ ), 15.0 (CH) ₃ , a). (The peak of 1,4-dioxane was used as a reference (δ = 68.1)).

(Example 2)
Surface Tension Measurement O-3Na obtained in Example 1 was dissolved in ultrapure water to prepare a dilute aqueous solution of O-3Na having various concentrations. The aqueous solution was placed in a petri dish and allowed to stand for 1 day, and then surface tension was measured (Kyowa DY-500) (Kyowa Interface Science, Saitama, Japan) at 25 ° C. by the Wilhelmy method. Similarly, measurements were also made for S-1Na, S-2Na, O-1Na and O-2Na. As a result, the critical micelle concentration (CMC) of O-3Na was 85 mM, the surface tension value at that time _{was 36.9 mN / m for γ CMC} , and the critical micelle concentration of other salts and the surface tension value at that time were It was found that it was as shown in FIG. In addition, the chelating ability of S-1Na, S-2Na and O-3Na to Ca was measured. The results are shown in FIG.

From this, the chelating ability for Ca was significantly improved with the dissociation of the three carboxyl groups of the ring-opening spicrysporic acid, and among them, the trisodium salt (O-3Na) of the ring-opening spicrysporic acid was excellent for Ca. It is understood that it has a chelating ability. It is considered that this is because the chelating ability is enhanced by the molecular assembly of O-3Na, and it is useful as a chelating agent in cosmetics, foods and the like.

(Example 3)
Particle size measurement of micelles formed by the trisodium salt (O-3Na) of ring-opening spicrysporic acid The particle size of micelles formed by O-3Na was measured by a dynamic light scattering method (DLS). A 100 mM O-3Na aqueous solution was prepared and filtered through a PVDF syringe filter (pores: 0.45 μm, Merck Millipore, USA, Massachusetts). Measurement was performed at ^{a scattering angle of 90 o} using an Ar laser (wavelength: 488 nm) using DLS7000 (Otsuka Electronics, Osaka, Japan). The results are shown in FIG. O-3Na formed micelles, the particle size of which was 3.4 ± 0.4 nm.

From this, it is understood that O-3Na forms micelles having a diameter about twice the molecular length thereof.

(Example 4)
Liquid crystal formation by selection of solvent Only O-3Na and water, or four kinds of solutions in which glycerin, 1,3-butanediol or sorbitol were further added to O-3Na and water, the concentration of each component was adjusted. , 3-Butanediol was added to form the liquid crystal only in the solution (Fig. 3).

The ability to form lyotropic liquid crystals was evaluated in a three-component system of O-3Na, water and 1,3-butanediol. Samples measured in test tubes to various concentrations were heated at 70 ° C. for about 20 minutes in a constant temperature bath, stirred with a vortex for about 3 minutes, and then allowed to stand at room temperature. A sample obtained by repeating this operation several times was used. A three-component phase diagram was prepared by visually observing this sample and observing it with a polarizing microscope (OLYMPUS BX41) (Olympus, Tokyo, Japan). The result is shown in FIG. It was found that O-3Na forms a lyotropic liquid crystal in a wide range. In addition, the fan-shaped texture peculiar to the hexagonal liquid crystal was obtained, suggesting the formation of the hexagonal liquid crystal among the riotropic liquid crystals.

In addition, a lyotropic liquid crystal could be formed in a three-component system of O-3Na, water, and 1-octanol. At the composition of O-3Na: water: 1-octanol = 63: 27:10 or 65:28: 7, a mosaic-like texture peculiar to the lamellar liquid crystal was observed, suggesting the formation of the lamellar liquid crystal ( FIG. 5).

It has been shown that the structure and / or pattern of the liquid crystal can be controlled by selecting the type and composition of the solvent.

(Example 5)
Liquid crystal formation with spicrysporic acid derivative salt S acid, S-1Na, S-2Na, O acid, O-1Na, O-2Na, or O-3Na were combined with water and 1-octanol to observe the formation of liquid crystal. .. When the concentration of each component was adjusted, a liquid crystal was not formed when S acid, S-1Na, S-2Na or O acid was used, and a lamellar liquid crystal was formed when O-1Na was used. Hexagonal liquid crystals were formed when -2Na or O-3Na was used.

It has been shown that the structure and / or pattern of the liquid crystal can be controlled by the selection of spicrysporic acid or a derivative thereof or a salt thereof.

(Example 6)
Synthesis of Mesoporous Silica (MS) Obtained Using Trisodium Salt (O-3Na) of Ring-Opening Spikrisporic Acid as a Template Mesoporous silica (MS) was synthesized using a liquid crystal formed from O-3Na as a template (Fig. 6). ). O-3Na was added to a water / ethanol mixed solution (water: ethanol = 3: 1 (volume ratio)) to prepare a 52 mM O-3Na solution, and the mixture was stirred for about 3 hours. Next, N-trimethoxysilylpropyl-N, N, N-trimethylammonium chloride (TMAPS) and tetraethoxysilane (TEOS) were added as silica sources in 1.0 equal amounts and 9.1 with respect to O-3Na, respectively. Equal amounts were added and the pH was adjusted to 10.0 with an aqueous sodium hydroxide solution. After stirring at 60 ° C. for 24 hours, the mixture was allowed to stand to promote the hydrolysis of silica. The resulting product was washed with a sufficient amount of water by suction filtration, dried (100 ° C., 10 hours, 1 ° C./min) and calcined (550 ° C., 5 hours, 1 ° C./min). O-3Na was thermally decomposed and removed to obtain a white powder.

(Example 7)
Performance Evaluation of Mesoporous Silica (MS) Obtained Using Trisodium Salt (O-3Na) of Ring-Opening Spikrisporic Acid as a Template In order to evaluate the pore characteristics of the white powder obtained in Example 5, nitrogen adsorption / desorption measurement was performed. (BELSORP-mini) (Microtrack Bell, Osaka, Japan) was performed. After pretreatment (300 ° C., 8 hours, vacuum), measurement was performed while maintaining a constant temperature (77K) with liquid nitrogen.

The obtained adsorption / desorption isotherm is shown in FIG. For comparison, mesoporous silica obtained using the anionic surfactant sodium dodecyl sulfate (SDS) as a template, SBA-15, for example, Dongyuan Zhao, Jianglin Feng, Qisheng Huo, Nicholas Melosh, Glenn H. Fredrickson, Bradley F. Chmelka, Galen D. Stucky. Science 279 (1998) 548-552. And Abdelhamid Syari, Bao-Hang Han, Yong Yang. J. AM. CHEM. SOC. 126 (2004) 14348-14349.) The results for mesoporous silica are also shown. Mesoporous silica using O-3Na as a template showed the highest amount of nitrogen adsorption. The amount of nitrogen adsorbed changed rapidly in the vicinity of the nitrogen partial pressure of 0.4 to 0.8, and the isotherm adsorption process and the desorption process did not match. This hysteresis is considered to be due to the capillary condensation phenomenon peculiar to the mesopores.

The table below shows the results of analyzing the specific surface area (BET method), total pore volume, and pore diameter (BJH method) of the obtained MS from the adsorption isotherm. _{The pore diameter (d BJH} ) of the MS using O-3Na as a template was 12.1 nm, and the total pore volume (V _total ) was 0.94 cm ³ / g, which were larger than those of other MSs. On the other hand, the specific surface area ( _SBET ) of mesoporous silica using O-3Na as a template was smaller than that of the others.
Table 1. Pore characteristics of each MS

In addition, SEM and TEM observations of mesoporous silica using O-3Na as a template were performed. In SEM, MS synthesized in a 20 mM O-3Na solution was observed, and in TEM, MS synthesized in a 52 mM O-3Na solution was observed. SEM (Hitachi S-4800) (Hitachi, Tokyo, Japan) attached a carbon tape to the center of the sample table, attached the sample to it, set the sample table on the device, and took an image. In addition, the retarding mode was set in order to observe at a higher magnification while reducing the damage to the sample. The acceleration voltage used was 0.5 to 1.0 kV. TEM (Hitachi H-7650) (Hitachi, Tokyo, Japan) adds ultrapure water to a powder sample, suspends it by vortex stirring, drops it on a Cu grid, and then puts it in a desiccator. It was dried for one day and imaged. An acceleration voltage of 120 kV was used. The results are shown in FIGS. 7 and 8. From the SEM image, the uneven structure of the surface was confirmed, and from the TEM image, it was confirmed that nanoparticles of about 5 nm were deposited, suggesting that pores were formed between these particles. By using O-3Na as a template, MS exhibiting excellent adsorption characteristics was synthesized.

It has been shown that a material having better properties than before can be prepared by microstructure control using a liquid crystal display formed from spicrysporic acid or a derivative thereof or a salt thereof.

(Note)
As described above, the present invention has been illustrated using the preferred embodiments of the present invention, but it is understood that the scope of the present invention should be interpreted only by the scope of claims. The patents, patent applications and documents cited herein are to be incorporated by reference in their content as they are specifically described herein. Understood.

The present invention can be used in cosmetics, microstructure control materials and their development.

Claims (18)

Spicrisporic acid

Or ring-opening spicy sporic acid

Alternatively, a liquid crystal which is a hexagonal liquid crystal or a lamellar liquid crystal containing a salt thereof and a solvent. Spicrisporic acid

Or ring-opening spicy sporic acid

Alternatively, a liquid crystal display containing the salt and a solvent containing alcohol. The liquid crystal according to claim 2, which is a lyotropic liquid crystal. The liquid crystal according to claim 3, which is a hexagonal liquid crystal or a lamellar liquid crystal. The liquid crystal display according to any one of claims 1 to 4, wherein the spicysporic acid or the ring-opening spicysporic acid or a salt thereof is a salt of the ring-opening spicysporic acid. The solvent is 1,3-butanediol, 1-octanol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, glycerin, polyglycerin, 1,2-hexanediol, 1,2-pentanediol, 3-methyl-. The liquid crystal according to any one of claims 1 to 5, which comprises an alcohol selected from the group consisting of 1,3-butanediol, erythritol, sorbitol, xylitol and combinations thereof. The liquid crystal display according to any one of claims 1 to 5, wherein the solvent contains 1,3-butanediol or 1-octanol. The cosmetic containing the liquid crystal according to any one of claims 1 to 7. The ring-opening spicysporic acid or the ring-opening spicysporic acid or a salt thereof is the ring-opening spicysporic acid.

The cosmetic product according to claim 8, which is a salt of the above. The cosmetic product according to claim 9, wherein the salt of the ring-opening spicrysporic acid is a salt in which one molecule of the ring-opening spicrysporic acid is combined with one molecule of a cationic species. The cosmetic product according to any one of claims 8 to 10, wherein the liquid crystal is a lamellar liquid crystal. The method for producing a liquid crystal according to any one of claims 1 to 7.
A production method comprising a step of mixing the solvent with the spicysporic acid or the ring-opening spicysporic acid or a salt thereof to form a liquid crystal display. It is a method for manufacturing a porous material.
Spicrisporic acid

Or ring-opening spicy sporic acid

Alternatively, a production method comprising a step of providing a composition containing a salt thereof and a solvent, and a step of preparing a porous material in the composition. The ring-opening spicysporic acid or the ring-opening spicysporic acid or a salt thereof is the ring-opening spicysporic acid.

The production method according to claim 13, which is a salt of the above. It is a method for manufacturing a porous material.
A production method comprising the step of providing the liquid crystal according to any one of claims 1 to 7 and the step of preparing a porous material using the formed liquid crystal as a template. The manufacturing method according to any one of claims 13 to 15, wherein the liquid crystal is a hexagonal liquid crystal. The production method according to any one of claims 13 to 16, wherein the porous material is mesoporous silica. A porous material produced by the production method according to any one of claims 13 to 17.

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