WO2013133419A1 - 新規糖誘導体ゲル化剤 - Google Patents
新規糖誘導体ゲル化剤 Download PDFInfo
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- WO2013133419A1 WO2013133419A1 PCT/JP2013/056493 JP2013056493W WO2013133419A1 WO 2013133419 A1 WO2013133419 A1 WO 2013133419A1 JP 2013056493 W JP2013056493 W JP 2013056493W WO 2013133419 A1 WO2013133419 A1 WO 2013133419A1
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- Prior art keywords
- gel
- gelling agent
- acid
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- compound
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- 239000003349 gelling agent Substances 0.000 title claims abstract description 201
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 103
- 229910001868 water Inorganic materials 0.000 claims description 103
- 239000000243 solution Substances 0.000 claims description 98
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- -1 amine hydrochloride Chemical class 0.000 claims description 50
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 40
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 36
- 230000002209 hydrophobic effect Effects 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000000463 material Substances 0.000 claims description 30
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 29
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 29
- 239000008103 glucose Substances 0.000 claims description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
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- 238000000034 method Methods 0.000 claims description 15
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- 229920000642 polymer Polymers 0.000 claims description 5
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 4
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 7
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0085—Immobilising or gelification of electrolyte
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Definitions
- the present invention relates to a novel gelling agent containing a sugar derivative.
- a structure in which a fluid is contained in a three-dimensional network structure formed by a substance having a gel forming ability is called a gel.
- a gel a structure in which a fluid is contained in a three-dimensional network structure formed by a substance having a gel forming ability
- a gelling agent a gelling agent
- the fluid is water, hydrogel (hydrogel), water Other organic liquids (organic solvents, oils, etc.) are called organogels or oil gels.
- Oil gels (organogels) are used to adjust the fluidity of cosmetics and paints in the fields of cosmetics, pharmaceuticals, agricultural chemicals, foods, adhesives, paints, resins, and the like.
- waste oil is gelled to prevent water contamination as a solid.
- urea compounds have been disclosed as low-molecular gelling agents that can form gels having excellent stability with a small amount of addition to various organic solvents (for example, Patent Document 1). 2). Further, it is disclosed that ⁇ -aminolactam derivatives have a gelling ability with respect to squalane, liquid paraffin and the like (for example, Patent Document 3). On the other hand, sugar derivatives derived from various monosaccharides have been reported to gel various types of organic solvents because of their structure that tends to form strong hydrogen bonds with each other (Non-patent Document 1).
- the present invention can not only gel water or oil (hydrophilic organic solvent and hydrophobic organic solvent) independently, but also a mixed solvent of water and oil (hydrophilic organic solvent and hydrophobic organic solvent), particularly water and A glucose-type gelling agent capable of gelling a mixed solvent of oil (hydrophobic organic solvent) was found and the present invention was completed.
- this invention relates to the gelatinizer which consists of a compound represented by following formula (1) or Formula (2) as a 1st viewpoint.
- R 1 and R 3 are each independently a linear or branched alkyl group having 1 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, or a group having 2 to 20 carbon atoms.
- n represents 0 or an integer of 1 to 4
- R 2 represents a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or an aryl group which may have a substituent
- R 4 and R 5 represent a hydroxy group.
- the compound represented by said Formula (1) is related with the gelatinizer as described in a 1st viewpoint which is a compound represented by Formula (3).
- the compound represented by said Formula (1) is related with the gelatinizer as described in a 1st viewpoint which is a compound represented by Formula (4).
- a hydrophobic organic solvent a hydrophilic organic solvent, water, a hydrophilic organic solution, a hydrophobic organic solution, or an aqueous solution A gel.
- the present invention relates to the gel according to the fourth aspect, wherein the hydrophobic organic solvent is at least one selected from the group consisting of vegetable oils, esters, silicone oils and hydrocarbons.
- the hydrophilic organic solvent is methanol, ethanol, 2-propanol, i-butanol, pentanol, hexanol, 1-octanol, isooctanol, acetone, cyclohexanone, acetonitrile, dioxane, glycerol, propylene glycol, ethylene glycol
- the gel according to the fourth aspect which is at least one selected from the group consisting of dimethyl sulfoxide.
- the present invention relates to the gel according to the fourth aspect, wherein the hydrophilic organic solution is a mixed solvent of the hydrophilic organic solvent and water according to the sixth aspect.
- the present invention relates to the gel according to the fifth aspect, wherein the hydrophobic organic solution is a mixed solvent of the hydrophobic organic solvent and water according to the fifth aspect.
- the aqueous solution is an organic acid, an inorganic acid, or at least one inorganic salt selected from the group consisting of an inorganic carbonate, an inorganic sulfate, an inorganic phosphate, and an inorganic hydrogen phosphate, or
- a gel according to the fourth aspect which is an aqueous solution in which at least one organic salt selected from the group consisting of acetate, lactate, citrate, organic amine hydrochloride and organic amine acetate is dissolved.
- the organic acid is at least one organic acid selected from the group consisting of acetic acid, citric acid, succinic acid, lactic acid, malic acid, maleic acid, fumaric acid and trifluoroacetic acid
- the inorganic acid is It is at least one inorganic acid selected from the group consisting of hydrochloric acid, phosphoric acid, carbonic acid, sulfuric acid, nitric acid and boric acid
- the inorganic salt is calcium carbonate, sodium carbonate, potassium carbonate, sodium sulfate, potassium sulfate, magnesium sulfate
- the present invention relates to a cosmetic base material or a medical base material comprising the gelling agent according to any one of the first aspect to the third aspect and at least one polymer compound.
- the gel electrolyte containing the gelatinizer as described in any one among a 1st viewpoint thru
- the present invention relates to a cell culture substrate containing the gelling agent according to any one of the first aspect to the third aspect.
- a 15th viewpoint it is related with the base material for biomolecule preservation
- a 16th viewpoint it is related with the base material for external use containing the gelatinizer as described in any one among a 1st viewpoint thru
- a 17th viewpoint it is related with the base material for biochemistry containing the gelatinizer as described in any one of a 1st viewpoint thru
- an 18th viewpoint it is related with the foodstuff base material containing the gelatinizer as described in any one among a 1st viewpoint thru
- the gelling agent of the present invention can form a gel in an aqueous system or an organic solvent system or in both systems. Moreover, the gelling agent of this invention can change the kind of solvent made to gelatinize by changing the kind of substituent on a sugar derivative. Furthermore, the gelling agent of the present invention has good storage stability.
- the gelling agent of the present invention uses a monosaccharide such as glucose, mannose, or a derivative thereof as a raw material, a gel excellent in biological safety can be formed.
- a monosaccharide such as glucose, mannose, or a derivative thereof
- the compound represented by the above formula (3) having a glucose moiety (hereinafter referred to as a glucose-type gelling agent) is widely used even in monosaccharides as the raw material glucose, Not only can the raw material costs for production be kept extremely low, but the total yield throughout the entire synthesis process of the gelling agent is high, and side reactions are unlikely to occur, making it easier to manufacture than conventional gelling agents. In addition, the manufacturing cost can be overwhelmingly reduced.
- the glucose type gelling agent has gel forming ability in both water and oil (hydrophobic organic solvent), and can form a water / oil dispersed gel.
- gelation of alcohol-based solvents is possible.
- a highly transparent gel can be formed with respect to water.
- the compound represented by the above formula (4) having a mannose moiety hereinafter referred to as a mannose type gelling agent
- a mannose type gelling agent is a highly transparent gel with respect to oil (hydrophilic organic solvent and hydrophobic organic solvent).
- a gel excellent in thixotropy can be obtained.
- it can form the transparent gel which can be self-supporting (it has self-supporting property), it is useful as a base material for sticks.
- the above-mentioned gelling agent can be produced from glucose or mannose derivatives in one pot, and a compound that can be easily and inexpensively produced as a gelling agent can be produced.
- a compound that can be easily and inexpensively produced as a gelling agent can be produced.
- no methanol or metal catalyst is required during production, it is possible to produce compounds that can be used as gelling agents for substrates that require high safety, such as cosmetic bases, medical bases, and food bases. it can.
- FIG. 1 is an HPLC chart of the purified compound [G3 ′′] prepared in the examples.
- FIG. 2 is a diagram showing a 1 H NMR (500 MHz, in heavy DMF) spectrum of the purified compound [G3 ′′] prepared in the examples.
- FIG. 3 is a diagram showing the stability of a SH245 gel prepared from mannose-type gelling agents: M1 and M3 and a known compound A (both 0.05 wt%) and SH245 at room temperature after standing for 7 days. is there.
- FIG. 4 is a view showing a micrograph of a water / oil-dispersed gel in isopropyl myristate (IPM) and water using glucose type gelling agent: G4 (1 wt%).
- IPM isopropyl myristate
- FIG. 5 is a view showing the appearance of a water / oil-dispersed gel in SH245 and water using glucose type gelling agent: G3 (0.25 to 1 wt%).
- FIG. 6 is a view showing a confocal laser scanning photomicrograph of SH245 using glucose type gelling agent: G3 (0.25 wt%) and a water / oil dispersion gel (stirring means: vortex mixer) in water.
- FIG. 7 is a view showing confocal laser scanning micrographs of a water / oil dispersion gel (stirring means: homogenizer) in SH245 and water using glucose type gelling agent: G3 (0.25 wt%).
- FIG. 8 is a view showing an appearance (FIG.
- FIG. 9 is a view showing the appearance of a gel taken out from a sample tube of squalene gel using mannose-type gelling agent: M3 (0.5 wt%).
- 9A is a view immediately after removal
- FIG. 9B is a view of the taken gel cut with a cover glass (thickness: 0.12-0.17 mm)
- FIG. 9C is cut. The figure of what overlapped the gel on the cut surfaces is shown, respectively.
- FIG. 10 is a graph showing the sol-gel phase transition temperature (T gel ) with respect to the concentration of the gelling agent in a toluene gel prepared using mannose type gelling agents: M1 to M6 and M8 and compound A which is a known substance. It is.
- FIG. 11 is a diagram showing the appearance of toluene gel (1 wt%) prepared using mannose-type gelling agent: M2 or compound A, which is a known substance, and SEM images of those xerogels.
- FIG. 12 is a diagram showing the appearance of toluene gels prepared using mannose-type gelling agent: M2 or M6 and AFM images of those xerogels.
- FIG. 13 is a view showing appearances of toluene gel (0.5 wt%) and water gel (0.1 wt%) prepared using mannose-type gelling agent: M2 and SEM images of these xerogels.
- FIG. 14 is a diagram showing the appearance of water gels (0.1 wt%) prepared using mannose-type gelling agent: M2 or glucose-type gelling agent G3 and SEM images of those xerogels.
- the gelling agent of the present invention comprises a compound represented by the following formula (1) or formula (2).
- R 1 and R 3 are each independently a linear or branched alkyl group having 1 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, or a group having 2 to 20 carbon atoms.
- n represents 0 or an integer of 1 to 4
- R 2 represents a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, or an aryl group which may have a substituent
- R 4 and R 5 represent a hydroxy group.
- linear alkyl group having 1 to 20 carbon atoms examples include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n- Octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n- Examples include octadecyl group, n-nonadecyl group, and n-eicosyl group.
- Examples of the branched alkyl group having 1 to 20 carbon atoms include isopropyl group, isobutyl group, sec-butyl group, tert-butyl group and 2-ethylhexyl group.
- Examples of the cyclic alkyl group having 3 to 20 carbon atoms include a group having a cyclopentyl ring and a cyclohexyl ring structure.
- Examples of the linear alkenyl group having 2 to 20 carbon atoms include vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, and decenyl group.
- Examples of the branched alkenyl group having 2 to 20 carbon atoms include 2-methyl-2-propenyl group, isopropenyl group, 2-methyl-1-propenyl group and 2-methylallyl group.
- Examples of the linear or branched alkyl group having 1 to 10 carbon atoms include the above-described exemplified linear alkyl group having 1 to 20 carbon atoms and the branched chain having 1 to 20 carbon atoms. Among chain alkyl groups, those having 1 to 10 carbon atoms can be mentioned.
- Examples of the aryl group include a phenyl group, a benzyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, and a 1-phenanthryl group.
- the aryl group may have a substituent, and examples of such a substituent include a linear, branched or cyclic alkyl group which may include an ester bond, an amide bond and an ether bond, and a halogen atom. An atom etc. are mentioned.
- R 2 is preferably a hydrogen atom or a methyl group from the viewpoint of satisfactorily gelling the solvent using the gelling agent of the present invention.
- R 1 is preferably a butyl group, a pentyl group, or a hexyl group.
- R 1 is preferably an octyl group, a decyl group, or a dodecyl group from the viewpoint that a highly transparent gel can be obtained without liquid separation when used for a hydrophilic organic solvent.
- a highly uniform gel can be obtained by mixing both of the organic solvent and the hydrophobic organic solvent such as oil, which may contain a hydrophilic organic solvent, respectively, or by mixing the two solvents.
- 1 is preferably a propyl group, a butyl group or a pentyl group.
- the compound represented by the above (1) or formula (2) can be obtained by a known method, for example, by reacting benzaldehyde dimethyl acetal having the above substituent on the benzene ring with a monosaccharide.
- the monosaccharide that can be used is not particularly limited as long as it is a monosaccharide having a pyranose ring structure, and examples thereof include allose, altrose, glucose, mannose, gulose, idose, galactose, and talose. Among them, glucose and mannose are preferable as monosaccharides from the viewpoint of being relatively inexpensive and particularly expected to be biocompatible.
- a compound represented by the following formula (3) having a glucose moiety or a compound represented by the following formula (4) having a mannose moiety is particularly preferable.
- R 1 , R 2 , R 3 and n are as defined in the formula (1).
- R 1 , R 2 , R 3 and n are as defined in the formula (1).
- the gelation ability of the compound represented by the above formula (3) (glucose type gelling agent) and the gelation ability of the compound represented by the above formula (4) (mannose type gelling agent).
- the compound (glucose-type gelling agent) represented by the above formula (3) is characterized by having a gel-forming ability in both water and oil (hydrophobic organic solvent), and is a water / oil mixed solvent.
- a water / oil-dispersed gel can be formed.
- gelation of an alcohol solvent is possible, and a highly transparent gel is formed with respect to water.
- the compound represented by the above formula (4) can form a highly transparent gel with respect to oil (hydrophilic organic solvent and hydrophobic organic solvent), and is excellent in thixotropic properties.
- a gel can be obtained.
- the transparent gel which can be self-supporting it has self-supporting property
- the gelation ability of the glucose-type gelling agent and the mannose-type gelling agent are different from each other, and application in a wide range of fields in accordance with each feature can be expected.
- the gel of the present invention can be obtained by gelling a solvent with the gelling agent. Specifically, a production method in which a predetermined amount of a gelling agent is dissolved in a solvent by heating and cooled is exemplified. Usually, it is preferable to dissolve completely by heating. In the present specification, gelation means that a fluid liquid loses fluidity. In the gelation of the solvent, the amount of the gelling agent of the present invention is not particularly limited as long as the effect of the present invention is exerted, but is usually 20 to 0.001% by mass, preferably Is 2 to 0.05 mass%.
- the solvent is not particularly limited as long as it does not prevent gelation.
- Preferred specific examples include a hydrophobic organic solvent, a hydrophilic organic solvent, water, a mixed solvent of water and a hydrophilic organic solvent (in this specification, hydrophilic A mixed solvent of hydrophobic organic solvent and water (referred to herein as a hydrophobic organic solution), or an organic acid or inorganic acid in water, or an inorganic salt or organic salt in water.
- An aqueous solution in which is dissolved referred to herein as an aqueous solution).
- hydrophobic organic solvent examples include vegetable oils such as olive oil, coconut oil, castor oil, jojoba oil or sunflower oil; esters such as cetyl octoate, isopropyl myristate or isopropyl palmitate; toluene, xylene, Examples thereof include hydrocarbons such as n-hexane, cyclohexane, octane, mineral oil, silicone oil or hydrogenated polyisobutene.
- vegetable oils such as olive oil, coconut oil, castor oil, jojoba oil or sunflower oil
- esters such as cetyl octoate, isopropyl myristate or isopropyl palmitate
- toluene, xylene examples thereof include hydrocarbons such as n-hexane, cyclohexane, octane, mineral oil, silicone oil or hydrogenated polyisobutene.
- the hydrophobic organic solvent olive oil, isopropyl myristate, toluene, cyclohexane, linear silicone, cyclic silicone, alkyl-modified silicone, phenyl-modified silicone, dimethicone, dimethiconol, and other silicone oils and octane are preferable.
- the silicone oil is a linear silicone (trade name: 2-1184), a cyclic silicone (trade name: SH245), an alkyl-modified silicone (trade name: SS-3408) available from Toray Dow Corning Co., Ltd. Phenyl-modified silicone (trade name: PH-1555), dimethicone (trade name: BY-11-0 series), dimethiconol (trade name: CB-1556) and the like can be used.
- the hydrophilic organic solvent means an organic solvent that dissolves in water at an arbitrary ratio, and examples thereof include alcohol, acetone, cyclohexanone, acetonitrile, dioxane, glycerol, and dimethyl sulfoxide.
- the alcohol is preferably a water-soluble alcohol that is freely soluble in water, and more preferable examples include alcohols having 1 to 9 carbon atoms, polyhydric alcohols, higher alcohols, and glycerides.
- the alcohol having 1 to 9 carbon atoms includes methanol, ethanol, 2-propanol, i-butanol, pentanol, hexanol, 1-octanol, isooctanol and the like;
- the polyhydric alcohol includes ethylene glycol
- Examples of the higher alcohol include octyldodecanol, stearyl alcohol, and oleyl alcohol;
- examples of the glycerides include trioctanoin, tri (caprylcaprylic acid) glyceryl, and stearic acid glyceryl.
- the hydrophilic organic solvents include methanol, ethanol, 2-propanol, i-butanol, pentanol, hexanol, 1-octanol, isooctanol, acetone, cyclohexanone, acetonitrile, dioxane, glycerol, propylene glycol, ethylene Glycol and dimethyl sulfoxide are preferred, and glycerol, propylene glycol and ethylene glycol are more preferred.
- a plurality of types of organic acids or inorganic acids may be added, and examples of preferable organic acids include acetic acid, citric acid, succinic acid, lactic acid, malic acid, maleic acid, fumaric acid and trifluoroacetic acid. More preferred are acetic acid, citric acid, succinic acid, lactic acid and malic acid, and more preferred are acetic acid, citric acid and lactic acid.
- examples of preferred inorganic acids include hydrochloric acid, phosphoric acid, carbonic acid, sulfuric acid, nitric acid and boric acid. More preferred are hydrochloric acid, phosphoric acid, carbonic acid and sulfuric acid, and further preferred are hydrochloric acid, phosphoric acid and carbonic acid.
- a plurality of inorganic salts or organic salts may be added, but one or two are preferable. It is also desirable that the solution has buffer capacity by adding two salts.
- preferred inorganic salts include inorganic carbonates, inorganic sulfates, inorganic phosphates, and inorganic hydrogen phosphates. More preferably, calcium carbonate, sodium carbonate, potassium carbonate, sodium sulfate, potassium sulfate, magnesium sulfate, potassium phosphate, sodium phosphate, disodium hydrogen phosphate or sodium dihydrogen phosphate, more preferably calcium carbonate, Magnesium sulfate, disodium hydrogen phosphate or sodium dihydrogen phosphate.
- organic salts examples include inorganic organic acid salts such as inorganic acetates, inorganic lactates and inorganic citrates, organic amine hydrochlorides and organic amine acetates. More preferred are sodium acetate, potassium acetate, sodium lactate, potassium lactate, sodium citrate, potassium citrate, ethylenediamine hydrochloride, ethylenediaminetetraacetate, and trishydroxymethylaminomethane hydrochloride.
- inorganic organic acid salts such as inorganic acetates, inorganic lactates and inorganic citrates, organic amine hydrochlorides and organic amine acetates. More preferred are sodium acetate, potassium acetate, sodium lactate, potassium lactate, sodium citrate, potassium citrate, ethylenediamine hydrochloride, ethylenediaminetetraacetate, and trishydroxymethylaminomethane hydrochloride.
- the gelling agent of the present invention is preferably 0.001 to 10% by mass with respect to the aforementioned hydrophobic organic solvent, hydrophilic organic solvent, water, hydrophilic organic solution, hydrophobic organic solution or aqueous solution as a medium. Is preferably used in an amount of 0.1 to 10% by mass, for example 0.1 to 5% by mass.
- the gelling agent of the present invention is added to the above-described hydrophobic organic solvent, hydrophilic organic solvent, water, hydrophilic organic solution, hydrophobic organic solution or aqueous solution, and dissolved by heating and stirring as necessary. Thereafter, the gel can be obtained by allowing it to stand at room temperature.
- the gel strength can be adjusted by the concentration of the gelling agent.
- the gel formed by the gelling agent of the present invention has various additives (surfactant, ultraviolet absorber, moisturizing agent) as needed, such as its application, within a range that does not inhibit the gelling ability of the gelling agent.
- additives surfactant, ultraviolet absorber, moisturizing agent
- Organic compounds such as agents, preservatives, antioxidants, fragrances, and physiologically active substances (medicinal ingredients), and inorganic compounds such as titanium oxide, talc, mica, and water) can be mixed.
- the cosmetic base material or medical base material of the present invention contains the gelling agent.
- the cosmetic base material or medical base material of the present invention may contain water, alcohol, polyhydric alcohol, hydrophilic organic solvent, hydrophobic organic solvent, or a mixed solution thereof in addition to the gelling agent. it can.
- examples of the alcohol, polyhydric alcohol, hydrophilic organic solvent, and hydrophobic organic solvent include the compounds exemplified above for the alcohol, polyhydric alcohol, hydrophilic organic solvent, and hydrophobic organic solvent.
- the cosmetic base material or medical base material of the present invention may contain additional components such as physiologically active substances and functional substances that are generally blended into the cosmetic base material or medical base material, if necessary.
- Such additive components include oil bases, moisturizers, feel improvers, surfactants, polymers, thickening / gelling agents, solvents, propellants, antioxidants, reducing agents, oxidizing agents, Preservatives, antibacterial agents, bactericides, chelating agents, pH adjusters, acids, alkalis, powders, inorganic salts, UV absorbers, whitening agents, vitamins and their derivatives, hair growth agents, blood circulation promoters, stimulants , Hormones, anti-wrinkle agents, anti-aging agents, anti-aging agents, cooling sensation agents, warming sensation agents, wound healing promoters, irritation mitigation agents, analgesics, cell activators, plant / animal / microbe extracts, antipruritic agents, keratin Stripping / dissolving agent, antiperspirant, cooling agent, astringent, enzyme, nucleic acid, fragrance, pigment, coloring , Dyes, pigments, anti-inflammatory agents, anti-inflammatory agents, anti-asthmatic, anti-chronic ob
- the cosmetic base material or medical base material of the present invention contains the gelling agent and at least one polymer compound.
- the polymer compound include gelatin, sodium alginate, propylene glycol alginate, gum arabic, polyvinyl alcohol, polyacrylic acid, sodium polyacrylate, carboxymethyl cellulose, gellan gum, xanthan gum, carrageenan polystyrene, polymethyl methacrylate, polyvinyl pyrrolidone, poly Examples include ethylene oxide, polylactic acid, polystyrene sulfonic acid, polyacrylonitrile, polyethylene, and polyethylene terephthalate.
- the gel electrolyte of the present invention is obtained by gelling an electrolyte solution (liquid electrolyte) composed of an organic solvent or water.
- the gelling agent and the electrolytic solution to be used are not particularly limited, and may be appropriately selected according to use.
- an electrolyte salt is dissolved in at least one aprotic organic solvent.
- the aprotic organic solvent include glyme, alkene carbonate, alkyl carbonate, cyclic ether, amides, nitriles, ketones and esters.
- Preferred specific examples include propylene carbonate, ethylene carbonate, diethyl carbonate, ⁇ -butyrolactone, 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, dimethyl sulfoxide, 1,3-dioxolane, formamide, dimethylformamide, 1,4-dioxane, acetonitrile, nitromethane, ethyl monoglyme, phosphoric acid triester , Trimethoxymethane, dioxolane derivative, sulfolane, 3-methyl-2-oxazolidinone, propylene carbonate derivative, tetrahydrofuran derivative, diethyl - ether and 1,3-propane sultone, and the like.
- the electrolyte salt includes a cation metal and a counter anion, and examples of the cation metal include Li + , Na + , K + , and the counter anion includes ClO 4 ⁇ , LiBF 4 ⁇ , PF 6 ⁇ , CF 3 SO.
- the gelling agent of the present invention and the gel obtained therefrom are a cell culture substrate, a substrate for preserving biomolecules such as cells and proteins, an external substrate, a biochemical substrate, a food substrate, a contact lens, It can be used for materials in various fields such as disposable diapers, artificial actuators, and dry land agricultural substrates. In addition, it can be widely used as a bioreactor carrier for enzymes and the like in research, medicine, analysis, and various industries.
- the present invention is also directed to a method for producing a compound represented by the formula (1) or the formula (2) which is the above-described gelling agent of the present invention. That is, the production method has the following formula [A]: (Wherein R 1 and R 3 are each independently a linear or branched alkyl group having 1 to 20 carbon atoms, a cyclic alkyl group having 3 to 20 carbon atoms, or the number of carbon atoms) An acetal derivative obtained by reacting a compound represented by 2 to 20 linear or branched alkenyl groups, n represents 0 or an integer of 1 to 4) with an acetalizing agent; Is carried out in one pot in the presence of ethanol and p-toluenesulfonic acid by subjecting the compound of formula (1) or formula (2) to a ring-condensation reaction with glucose or mannose or a derivative thereof. It is the method characterized by this.
- Sodium sulfate (special grade), sodium chloride (special grade), sodium hydrogen carbonate (special grade), and diethyl ether (special grade) used during post-reaction treatment and purification were obtained from Wako Pure Chemical Industries, Ltd., hexane (special grade), acetic acid Ethyl (special grade), chloroform (special grade), and diisopropyl ether (special grade) were obtained from Kanto Chemical Co., Inc.
- Deuterated chloroform (containing 0.03% TMS (tetramethylsilane)) and deuterated dimethylformamide used for NMR measurement were obtained from Sigma-Aldrich Japan.
- Surfactant Polyoxyethylene sorbitan monolaurate (Tween 20), sodium dodecyl sulfate (SDS, primary), stearyltrimethylammonium bromide (STAB), 3-[(3-cholamidopropyl) dimethylammonio] propanesulfonate (CHAPS) ) was obtained from Wako Pure Chemical Industries.
- Example 1 Synthesis of gelling agent
- a compound that becomes a mannose-type gelling agent and a glucose-type gelling agent can be synthesized according to Scheme A shown below.
- the aromatic aldehyde compound having various hydrocarbon groups as a raw material for the gelling agent a commercially available one is obtained by purchase (see above), and a non-commercial one is synthesized according to Scheme 1 described later.
- the ring condensation reaction between an aromatic aldehyde compound and a sugar is generally carried out via an acetal or from an aldehyde under heating conditions.
- One of the characteristics is that it can be obtained from an aldehyde compound at room temperature by a one-stage condensation reaction.
- Examples 2 to 17 Gel forming ability of gelling agent and various evaluations of the obtained gel
- gelling agents Using the compounds M1-M10, G1-G9, and G11-G13 synthesized in Example 1 as gelling agents, gel formation ability (gelation ability) in various solvents and various evaluations of the obtained gel were performed.
- compound A methyl ⁇ -D-4,6-benzylidenemannose known as a known substance (Non-patent Document 1) and compound B: gelation ability with methyl ⁇ -D-4,6-benzylidene glucose
- Non-patent Document 1 Non-patent Document 1
- compound B gelation ability with methyl ⁇ -D-4,6-benzylidene glucose
- Example 2 Comparison of gelling ability with known substances
- the gelation test was performed as follows. Add a gelling agent and various solvents to a 4 mL screw mouth sample tube, 90 ° C for cyclohexane, acetonitrile, methanol, ethanol, ethanol / water mixed solvent, 100 ° C for toluene, water, DMSO / water mixed solvent, octane, SH245, Olive oil, isopropyl myristate, ethylene glycol, and glycerol were each heated and dissolved at 120 ° C. for 30 minutes. The resulting solution was cooled to room temperature and allowed to stand for 1 hour to observe gel formation.
- the numbers in the table indicate the minimum gelation concentration (wt%), the code in the table indicates the state of the gel formed, the transparent gel is "G”, the translucent gel is “#G”, the cloudy gel “* G”, crystallized “Cr”, and partially gelled “PG”.
- Gelling agent: “ ⁇ ” means that gelation did not occur even at a concentration of 2 wt%.
- Table 1 shows the results of gelation tests of compounds M1 to M10, which are mannose-type gelling agents, and the above-mentioned A compound
- Table 2 shows the results of gelation tests of compounds G3 and G8, which are glucose-type gelling agents, and the above-mentioned B compound. Respectively.
- the gelling agent of the present invention forms a highly transparent gel with respect to various solvents as compared with the gelling agent using Compound A or Compound B, which is a known substance. And the lowest gelling concentration was shown to be low.
- the gelling agent of the present invention is a compound obtained by introducing a hydrocarbon group, which is a hydrophobic functional group, into compound A or compound B, which is a known substance, but it is a nonpolar solvent (octane, toluene).
- octane, toluene a nonpolar solvent
- the gel forming ability to polar solvents having high polarity water, ethanol, ethylene glycol
- G3 which is a glucose type gelling agent, formed a gel that was relatively transparent to water.
- Example 3 Thixotropic test
- the thixotropic properties of various gels composed of mannose type gelling agents were evaluated.
- the thixotropy test was performed as follows. A gel at the lowest gelation concentration was prepared in the same manner as in Example 2. Then, the gel was disintegrated by shaking until it became a sol state from the gel using a vortex mixer, and allowed to stand at room temperature for 1 hour. After 1 hour, the sample tube containing the solution was turned upside down, and when the solution did not flow down, it was judged as “thixotropic”. The results obtained are shown in Table 5. In the table, “ ⁇ ” indicates that thixotropic properties were determined, “ ⁇ ” indicates that thixotropic properties were not determined, and “ ⁇ ” indicates that no gel was formed.
- the gelling agent of the present invention into which a hydrocarbon group was introduced as compared with the known compound A was obtained to form a gel having thixotropic properties.
- Example 4 Storage stability
- the gelling agent of the present invention has a smaller amount of liquid separation than the gelling agent using Compound A, which is a known substance, and obtained a result that it is excellent in storage stability.
- the amount of liquid separation decreases, suggesting that the storage stability of the gel is greatly involved in the alkyl chain length. The result was obtained.
- Example 5 Gelling test of glucose type gelling agent
- the result that it has chemical ability was obtained.
- the result which suggested that the gel which is excellent in thixotropic property and storage stability by the introduction of an alkyl chain was obtained was obtained.
- Example 6 Thixotropic test of alcohol-containing aqueous gel
- Example 5 From the alcohol blending test in Example 5, the amount of alcohol that can be blended with each glucose-type gelling agent was clarified. Therefore, as in Example 3, a thixotropic test of an alcohol-containing aqueous solution gel was performed.
- the thixotropy test was performed as follows. First, the gel preparation was performed in the same manner as in Example 5, and the thixotropic test was performed in the same manner as in Example 3. At this time, the concentration of the gelling agent was prepared from the lowest gelation concentration, and gradually increased until the thixotropic property was expressed, and the expression of thixotropic property was observed. The results are shown in Table 7.
- the numbers in the table (bottom) indicate the concentration (wt%) of the gelling agent that developed thixotropic properties, and the numbers and symbols in () (upper) indicate the minimum gelation concentration and gel concentration shown in Example 5. Represents a state.
- Compound B which is a known substance, reprinted the results shown in Example 2.
- the concentration of the set gelling agent is 0.1, 0.25, 0.5, 1.0, 2.0 wt%. However, those that did not develop thixotropic properties within the set concentration range were indicated as “x”.
- thixotropic expression was confirmed as the chain length of the alkyl chain of the hydrocarbon group bonded to the benzene ring of the gelling agent compound increased.
- compound B which is a known compound, no thixotropic expression was confirmed.
- G or #G the results were obtained that they tend to develop thixotropic properties near the lowest gelation concentration.
- Example 7 Additive compounding test
- antiseptics and surfactants are blended in cosmetics and quasi drugs.
- gelling agent of the present invention the possibility of gelation when a preservative and a surfactant were blended was examined.
- the preservative blending test was conducted as follows. An aqueous solution containing a preservative in which the preservative was dissolved in water to a predetermined concentration was prepared. Thereafter, a gelling agent (glucose-type gelling agent: G3) was added to a 4 mL screw tube so as to have a predetermined concentration, the previously prepared preservative-containing aqueous solution was added, and the mixture was heated and dissolved at 100 ° C. for 30 minutes. The resulting solution was cooled to room temperature, allowed to stand for 1 hour, and the formation of gel was confirmed by inverting the screw tube. The results are shown in Table 8. The preservatives used were methylparaben and phenoxyethanol each alone and a mixture thereof.
- the gelling agent of the present invention obtained a result of forming a gel even when a preservative was blended.
- the surfactant blending test was performed as follows. A surfactant-containing aqueous solution in which a surfactant was dissolved in water to a predetermined concentration was prepared. Thereafter, a gelling agent (glucose-type gelling agent: G3) was added to a 4 mL screw tube to a predetermined concentration, the previously prepared surfactant-containing aqueous solution was added, and the mixture was heated and dissolved at 100 ° C. for 30 minutes. . The resulting solution was cooled to room temperature, allowed to stand for 1 hour, and the formation of gel was confirmed by inverting the screw tube. The results are shown in Table 9.
- the surfactant used was polyoxyethylene sorbitan monolaurate (Tween 20), a nonionic surfactant, sodium dodecyl sulfate (SDS), an anionic surfactant, and stearyltrimethylammonium, a cationic surfactant.
- Teween 20 polyoxyethylene sorbitan monolaurate
- SDS sodium dodecyl sulfate
- anionic surfactant sodium dodecyl sulfate
- stearyltrimethylammonium a cationic surfactant.
- STAB and the amphoteric surfactant 3-[(3-cholamidopropyl) dimethylammonio] propanesulfonate (CHAPS).
- the gelling agent of the present invention obtained a result of forming a gel even when a surfactant was blended.
- Example 8 Water-oil dispersion test using glucose type gelling agent
- a surfactant is generally used to uniformly disperse and stabilize the oil and water.
- the gelling agent of the present invention forms a good gel even when the surfactant is blended was obtained.
- the gelling agents of the present invention particularly glucose type gelling agents: G1 to G4, obtained a result that both water and oil-based solvent form a gel. Yes.
- a water-oil dispersion test was conducted to confirm whether the gelling agent of the present invention can uniformly disperse both water and oil solvents.
- the water-oil dispersion test was performed as follows. A gelling agent (glucose-type gelling agent: G4 or G5) and various solvents were added to a 4 mL screw mouth sample tube so as to have a predetermined concentration, and heated and dissolved at 100 ° C. for 30 minutes. Then, after shearing for 2 minutes using a vortex mixer, the mixture was allowed to stand at room temperature for 1 hour, and the dispersion state was observed. After cooling, the fluidity of the solution was lost, the state in which the solution did not flow down even when the sample tube was inverted, and the state in which water and oil were uniformly dispersed were judged as “water / oil dispersion gel”.
- a gelling agent glue-type gelling agent: G4 or G5
- various solvents were added to a 4 mL screw mouth sample tube so as to have a predetermined concentration, and heated and dissolved at 100 ° C. for 30 minutes. Then, after shearing for 2 minutes using a vortex mixer, the mixture
- the minimum concentration (wt%) of the gelling agent required for the water / oil-dispersed gel was defined as the minimum gelation concentration.
- Table 10 shows the obtained results. The numbers in the table indicate the minimum gelation concentration, “G” for water / oil dispersion gel, “W-sol” for water / oil dispersion but fluidity, “PG” for partially gelled. " In the water-oil dispersion test, G4 having a gelling ability with respect to both water and an oil agent and G5 having a gelling ability only for the oil agent were used. The concentration of these gelling agents was 2.0, 1.0, 0.5, 0.25, and 0.1 wt%.
- FIG. 4 shows the results of optical microscope observation of a water / oil-dispersed gel in isopropyl myristate (IPM) using G4 as a gelling agent and water.
- the droplets observed by optical microscope observation were about 10 to 50 ⁇ m.
- FIG. 5 shows the appearance of the water / oil dispersion gel obtained.
- FIG. 6 shows the results of observation of the water / oil-dispersed gel with a confocal laser scanning microscope.
- the minimum gelation concentration is low, the range of the blending ratio of water and oil is wide, and a good water / oil dispersion gel is formed. Obtained.
- the droplets observed were about 10 to 50 ⁇ m, and the results were obtained to have a relatively uniform size.
- Example 9 Water-oil dispersion test using a homogenizer
- a vortex mixer was used for stirring performed after the gelling agent was dissolved in a solvent by heating.
- a water-oil dispersion test was performed using a homogenizer which is a stirring means having higher shear. By applying high shear with a homogenizer, it is assumed that the droplets formed are smaller.
- the water-oil dispersion test using a homogenizer was performed as follows. Glucose-type gelling agent: G3 (0.25 wt%) and solvent (SH245 and water mixed system: 30/70 to 70/30 (vol / vol)) were added to the test tube, and 30 ° C. at 100 ° C. in the dry bath. It was dissolved by heating for minutes. Then, after shearing for 5 minutes using a homogenizer, the mixture was allowed to stand at room temperature for 1 hour, and the dispersion state was observed with a confocal laser scanning microscope. The results are shown in FIG.
- a uniform water / oil-dispersed gel was also formed by a stirring method using a homogenizer. From the confocal laser scanning microscope, the maximum size of droplets formed using a homogenizer is about 30 ⁇ m (FIG. 7), and the size of droplets using a vortex mixer (10 to 50 ⁇ m: FIG. 6). ) And a relatively small droplet was obtained. That is, a result suggesting that the droplet diameter in the obtained water / oil dispersion can be controlled by controlling the shear rate after the gelling agent is dissolved by heating.
- Example 10 Premix test
- the gelling agent (compound) powder was added to various solvents and then heated and dissolved to perform each test. In this method, it takes time until the gelling agent powder is dissolved in various solvents, and it is difficult to say that it is a general-purpose method due to the difference in dissolution time in various solvents. If it is possible to quickly prepare a gel or water / oil dispersion gel by preparing in advance a dispersion in which a powder gelling agent is dissolved at a high concentration and adding the dispersion to various solvents, From the viewpoint of the gel preparation process, it is considered to be a quick and simple technique.
- a method of adding a high-concentration dispersion of a gelling agent to various solvents later to form a gel or a water / oil-dispersed gel is defined as “premix” in this specification.
- premix In order to conduct a premix test to determine whether the gelling agent of the present invention can be applied to a premix, first, a dispersion capable of dissolving the gelling agent at a high concentration was examined.
- an alcohol solvent such as ethanol (EtOH), propylene glycol (PG), butylene glycol (BG), pentylene glycol (PenG), and glycerin (Gly) was selected.
- EtOH ethanol
- PG propylene glycol
- BG butylene glycol
- PenG pentylene glycol
- Gly glycerin
- dispersions prepared by adding G4 to various alcohol solvents at a concentration of 10 wt% were ethanol, propylene glycol, butylene glycol, and pentylene glycol were uniformly dissolved when heated, and after cooling, It was confirmed that it was redissolved at 80 ° C.
- glycerin was confirmed to be undissolved in both heating and reheating, and the solubility was insufficient as a 10 wt% G4 dispersion, and it was judged to be unsuitable for a premix dispersion.
- propylene glycol that could be re-dissolved was selected as the solvent of the dispersion, and a premix test was performed according to the following procedure.
- the gel prepared from the gelling agent of the present invention is a gel having a self-supporting hardness, while it is very weak against shearing, exhibits liquidity, and has a characteristic of solidifying immediately after shearing. From these characteristics, the prepared gel can be easily taken out from the container, can be easily cut with a sharp blade, and the shape of the gel can be maintained without liquid separation after cutting.
- FIG. 9 shows a photograph of the appearance of the gel taken out from the sample tube.
- FIG. 9 (A) shows a state immediately after taking out
- FIG. 9 (B) shows a cut out gel with a cover glass (thickness: 0.12-0.17 mm)
- FIG. 9 (A) shows a state immediately after taking out
- FIG. 9 (B) shows a cut out gel with a cover glass (thickness: 0.12-0.17 mm)
- FIG. 9 (C) shows a cut surface of the cut gel. It is a photograph of what was superimposed on each other. As shown in FIG. 9, the taken-out gel is self-supporting (self-supporting), maintains the shape of the gel without liquid separation after shearing, and can be re-adhered when overlapped between cut surfaces. The result was that it was a gel that could have self-healing properties.
- G4 glucose gelling agent
- M3 mannose gelling agent
- G4 a gel removal test was performed using G4 which is a glucose gelling agent.
- a glucose gelling agent (G4) and various solvents were added to the sample tube to a predetermined concentration, and then dissolved by heating at 120 to 130 ° C. for 30 minutes. Thereafter, the solution (about 2 mL) was poured into a standing cylindrical tube and allowed to cool to room temperature for 1 hour to prepare a gel.
- a gel removal test was performed by slowly extruding the gel from a cylindrical tube. The results are shown in Table 13. The symbols in the table were determined to be “ ⁇ ” if the gel shape was maintained after removal, “ ⁇ ” if it was slightly loose, and “x” if the shape could not be maintained. Unimplemented items are indicated by hatching.
- Example 12 Spray test
- the gel prepared from the gelling agent of the present invention is a gel having a self-supporting hardness, while it is very weak against shearing, exhibits liquidity, and shears. After that, it has the characteristic of solidifying immediately. From these characteristics, when the gel of the present invention is used in a sprayer such as a spray generally used in cosmetics, a uniform spray can be expected, and immediately after spraying, the gel is formed without dripping. It is expected to have good coating properties.
- the spray test was conducted as follows. Glucose type gelling agent (G3, G6) and water / ethanol mixed solvent (75/25 or 50/50 (vol / vol) (4 mL) are added to the sample tube to 0.25 wt%, and 30 at 80 ° C. Then, the solution was transferred to a spray vial tube (manufactured by Maruemu Co., Ltd., No. 3L) and allowed to cool to room temperature for 1 hour to prepare a gel containing a spray vial tube.
- Glucose type gelling agent G3, G6
- water / ethanol mixed solvent 75/25 or 50/50 (vol / vol) (4 mL)
- the spray vial tube gel was sprayed from a distance of 4 cm toward a glass plate (10 ⁇ 7.5 cm) to evaluate whether or not spraying was possible, and the spread of the sprayed gel (length and length) The result of the spray test is shown in Table 14.
- Example 13 Sol-gel phase transition temperature
- T gel The sol-gel phase transition temperature (T gel ) of toluene was measured.
- a sample tube containing a gel prepared with a mannose-type gelling agent (M1 to M6, M8) or a known compound A and toluene was placed in a temperature-controlled dry bath and allowed to stand at 25 ° C. for 5 minutes. After placing, the sample tube was taken out from the dry bath and turned over to check whether the gel became a solution and dropped downward. When the gel state was maintained, the dry bath was set at 30 ° C., and the sample tube containing the gel was placed and allowed to stand for 5 minutes, and then the same operation was performed.
- FIG. 10 shows the sol-gel phase transition temperature (T gel ) with respect to the concentration of the gelling agent in the toluene gel of each gelling agent.
- Table 15 shows the concentration of the gelling agent and the sol-gel phase transition temperature (T gel ) in the SH245 gel prepared at the lowest gelation concentration by changing the solvent to SH245 by the same test.
- the sol-gel phase transition temperature T gel tends to increase as the concentration of the gelling agent increases, and the carbonization bonded to the benzene ring of the gelling agent is observed.
- the longer the alkyl chain length of the hydrogen group the lower the sol-gel transition temperature. This is thought to be due to the increased affinity of the gelling agent itself for the solvent.
- the gelling agents M2 (CH 3 (CH 2 ) 3 O—) and M8 (3-butenyl-O—) having the same alkyl chain length are compared, the sol-gel transition temperature is increased by introducing an olefin structure at the alkyl terminal. I got the result to go up.
- the SH245 gel obtained using the gelling agents M1 to M6 and M8 has a higher sol-gel phase transition temperature compared to the known gelling agent compound A which is a known substance. To get the result. This indicates that the gelling agent of the present invention can prepare a thermally stable gel as compared with the known compound A.
- Example 14 Toluene gel (xerogel) SEM observation
- Manxose-type gelling agent prepared in Example 1 M2 or toluene gel containing 1 wt% of known substance Compound A was prepared, and then the gel was vacuum dried for 24 hours to obtain a xerogel obtained by scanning microscope ( (SEM). The obtained results are shown in FIG. From the SEM image shown in FIG. 11, a fiber-like image having a width of about 500 nm to 800 nm was obtained with the gelling agent A toluene gel (xerogel), whereas the gelling agent M2 toluene gel (xerogel) had a plate shape. A shaped image was obtained.
- Example 15 AFM observation of toluene gel (xerogel) using gelling agent M2 or M6]
- M2 mannose-type gelling agent synthesized in Example 1
- M6 0.02 wt%
- AFM image was observed.
- a toluene solution to which mannose-type gelling agent synthesized in Example 1: M2 (0.02 wt%) or M6 (0.02 wt%) was added was prepared by heating at 100 ° C., and this was placed on a graphite substrate (HOPG). After casting, the mixture was allowed to stand for 1 hour and then vacuum dried for 24 hours, and HOPG was observed with an atomic force microscope (AFM).
- AFM atomic force microscope
- FIG. 12 the external appearance photograph of the gel gelatinized by the minimum gelation density
- the gel (xerogel) prepared from the toluene solution of the gelling agent M2 was obtained to have a fiber structure whose height from HOPG was about 3.5 nm. From this result, it can be seen that the plate-like body of the gelling agent M2 seen in the SEM image of Example 13 is a plate-like bundle of fiber structures having a width of about 3.5 nm.
- the gel (xerogel) prepared from the gelling agent M2 and M6 in toluene solution is compared and observed by AFM, the gel prepared from the M2 toluene solution (xerogel) forms a fiber structure with a height of about 3.5 nm.
- the fiber having a height of 3.1 nm to 3.8 nm was bundled to obtain a tape-like structure.
- Example 16 SEMM observation of toluene gel and water gel (xerogel) using gelling agent M2
- Mannos type gelling agent prepared in Example 1 Toluene gel added with 0.5 wt% of M2 and water gel added with 0.1 wt% were prepared, and the xerogel obtained by lyophilizing each for 24 hours was stored in SEM. And observed. The obtained result is shown in FIG. From the SEM image shown in FIG. 13, it was found that the toluene gel (xerogel) was a plate-like body in which fibers were bundled, whereas the water gel (xerogel) formed a fiber structure with a width of about 200 nm. Obtained.
- Example 17 SEM observation of water gel (xerogel)]
- M2 or glucose-type gelling agent: G3 prepared in Example 1, and observe the xerogel obtained by freeze-drying for 24 hours with SEM did.
- the obtained result is shown in FIG. From the SEM image shown in FIG. 14, the water gel (xerogel) using M2 forms a fiber structure having a width of about 200 nm, whereas the water gel (xerogel) using G3 is a fiber having a width of about 40 to 50 nm. The result that the structure was formed was obtained. In this way, in water gel, the structure of the sugar part of the gelling agent is changed from mannose to glucose, so that the transparency of the gel is increased and the width of the fiber structure composed of each gelling agent tends to be narrowed. It became the result.
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Abstract
Description
ゲル化剤についての研究は、主に高分子化合物について行われてきたが、近年では、高分子化合物に比べて、多様な機能の導入が容易な低分子化合物についての研究開発が進められている。上述したように、オイルゲル(オルガノゲル)は幅広い分野での利用がされており、今後も利用分野の拡大が期待されている。このため、低分子化合物のゲル化剤(以下、低分子ゲル化剤ということがある)には、オイルゲルの用途拡大に当たり、広範な種類の有機溶剤に対するゲル形成能力が求められている。こうした課題に対し、これまでにも、種々の有機溶剤に対して少量の添加量で安定性に優れるゲルを形成できる低分子ゲル化剤として、尿素化合物が開示されている(例えば、特許文献1、2)。また、α-アミノラクタム誘導体がスクアランや流動パラフィン等に対してゲル化能を有することが開示されている(例えば特許文献3)。
一方、各種単糖類から誘導された糖誘導体は互いに強い水素結合をとりやすい構造のため、様々な種類の有機溶媒をゲル化することが報告されている(非特許文献1)。
また、水と油(親水性有機溶媒及び疎水性有機溶媒)の両方の溶媒をゲル化できるゲル化剤の報告例は本発明者の知る限りこれまでなく、斯様なゲル化性能を発揮するゲル化剤の開発がこれまで望まれてきた。特に、水と油(疎水性有機溶媒)の混合溶媒を界面活性剤等を使用せずともゲル化できるゲル化剤は、生体安全性の高さが求められる化粧品や医薬品基材において有用であるものの、そのような画期的なゲル化剤の提案はこれまでなされていない。
本発明は、上記の事情に基づいてなされたものであり、その解決しようとする課題は、これまで提案されていない構造を有する新規なゲル化剤を提供することにある。特に本発明は、水又は油(親水性有機溶媒及び疎水性有機溶媒)をそれぞれ単独でゲル化できるだけでなく、水と油(親水性有機溶媒及び疎水性有機溶媒)の混合溶媒、特に水と油(疎水性有機溶媒)の混合溶媒についてもゲルすることができるグルコース型のゲル化剤を見出し、本発明を完成させた。
すなわち、本発明は、第1観点として、下記式(1)又は式(2)で表される化合物からなるゲル化剤に関する。
R1及びR3は、それぞれ独立して、炭素原子数1乃至20の直鎖状若しくは分岐鎖状のアルキル基、炭素原子数3乃至20の環状のアルキル基、又は炭素原子数2乃至20の直鎖状若しくは分岐鎖状のアルケニル基を表し、nは0又は1~4の整数を表し、
R2は、水素原子、炭素原子数1乃至10の直鎖状又は分岐鎖状のアルキル基、又は置換基を有していてもよいアリール基を表し、
R4及びR5は、ヒドロキシ基を表す。)
第2観点として、前記式(1)で表される化合物は式(3)で表される化合物である、第1観点に記載のゲル化剤に関する。
第3観点として、前記式(1)で表される化合物は式(4)で表される化合物である、第1観点に記載のゲル化剤に関する
第4観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤と、疎水性有機溶媒、親水性有機溶媒、水、親水性有機溶液、疎水性有機溶液又は水溶液よりなるゲルに関する。
第5観点として、前記疎水性有機溶媒が植物油、エステル類、シリコーン油及び炭化水素類からなる群から選択される少なくとも一種である、第4観点に記載のゲルに関する。
第6観点として、前記親水性有機溶媒がメタノール、エタノール、2-プロパノール、i-ブタノール、ペンタノール、ヘキサノール、1-オクタノール、イソオクタノール、アセトン、シクロヘキサノン、アセトニトリル、ジオキサン、グリセロール、プロピレングリコール、エチレングリコール及びジメチルスルホキシドからなる群から選択される少なくとも一種である、第4観点に記載のゲルに関する。
第7観点として、前記親水性有機溶液が第6観点に記載の親水性有機溶媒と水との混合溶媒である、第4観点に記載のゲルに関する。
第8観点として、前記疎水性有機溶液が第5観点に記載の疎水性有機溶媒と水との混合溶媒である、第5観点に記載のゲルに関する。
第9観点として、前記水溶液が有機酸、又は、無機酸、又は、無機炭酸塩、無機硫酸塩、無機リン酸塩及び無機リン酸水素塩からなる群から選択される少なくとも一種の無機塩、又は、酢酸塩、乳酸塩、クエン酸塩、有機アミン塩酸塩及び有機アミン酢酸塩からなる群から選択される少なくとも一種の有機塩を溶解させた水溶液である、第4観点に記載のゲルに関する。
第10観点として、前記有機酸が酢酸、クエン酸、コハク酸、乳酸、リンゴ酸、マレイン酸、フマル酸及びトリフルオロ酢酸からなる群から選択される少なくとも一種の有機酸であり、前記無機酸が塩酸、リン酸、炭酸、硫酸、硝酸及びホウ酸からなる群から選択される少なくとも一種の無機酸であり、前記無機塩が、炭酸カルシウム、炭酸ナトリウム、炭酸カリウム、硫酸ナトリウム、硫酸カリウム、硫酸マグネシウム、リン酸カリウム、リン酸ナトリウム、リン酸水素二ナトリウム及びリン酸二水素ナトリウムからなる群から選択される少なくとも一種の無機塩であり、前記有機塩が、酢酸ナトリウム、酢酸カリウム、乳酸ナトリウム、乳酸カリウム、クエン酸ナトリウム、クエン酸カリウム、エチレンジアミン塩酸塩、エチレンジアミン四酢酸塩及びトリスヒドロキシメチルアミノメタン塩酸塩からなる群から選択される少なくとも一種の有機塩である、第9観点に記載のゲルに関する。
第11観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、化粧品基材又は医療用基材に関する。
第12観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤及び少なくとも1種の高分子化合物を含む、化粧品基材又は医療用基材に関する。
第13観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、ゲル電解質に関する。
第14観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、細胞培養基材に関する。
第15観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、生体分子保存用基材に関する。
第16観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、外用基材に関する。
第17観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、生化学用基材に関する。
第18観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、食品用基材に関する。
第19観点として、第1観点乃至第3観点のうち何れか1つに記載のゲル化剤を含む、乾燥地農業用基材に関する。
第20観点として、第1観点に記載の式(1)又は式(2)で表される化合物を製造する方法において、
下記式[A]
特にグルコース部分を有する上記式(3)で表される化合物(以下、これをグルコース型ゲル化剤という)は、原料であるグルコースが単糖類の中でも汎用的に扱われており、ゲル化剤の製造にかかる原料コストを極めて低く抑えられるだけでなく、ゲル化剤の合成の全過程を通してのトータル収率が高く、しかも副反応が起こりにくいため、従来のゲル化剤と比べて製造が容易であり且つ製造コストを圧倒的に低く抑えることができる。また、グルコース型ゲル化剤は、水と油(疎水性有機溶媒)のいずれにおいてもゲル形成能を有し、水/油分散型ゲルを形成することができる。またアルコール系溶媒のゲル化を可能とする。このため、幅広い特性を有する媒体を透明且つ低濃度でゲル化できる汎用性の高いゲル化剤となる。特に水に対して透明性の高いゲルを形成できる。
一方、マンノース部分を有する上記式(4)で表される化合物(以下、これをマンノース型ゲル化剤という)は、油(親水性有機溶媒および疎水性有機溶媒)に対して透明性の高いゲルを形成し得、またチキソトロピー性に優れるゲルを得ることができる。そして自立可能(自己支持性を有する)である透明なゲルを形成できるため、スティック用基材として有用である。
本発明のゲル化剤は、下記式(1)又は式(2)で表される化合物からなる。
R1及びR3は、それぞれ独立して、炭素原子数1乃至20の直鎖状若しくは分岐鎖状のアルキル基、炭素原子数3乃至20の環状のアルキル基、又は炭素原子数2乃至20の直鎖状若しくは分岐鎖状のアルケニル基を表し、nは0又は1~4の整数を表し、
R2は、水素原子、炭素原子数1乃至10の直鎖状又は分岐鎖状のアルキル基、又は置換基を有していてもよいアリール基を表し、
R4及びR5は、ヒドロキシ基を表す。)
前記炭素原子数1乃至20の分岐鎖状のアルキル基としては、イソプロピル基、イソブチル基、sec-ブチル基、tert-ブチル基及び2-エチルヘキシル基等が挙げられる。
前記炭素原子数3乃至20の環状のアルキル基としては、シクロペンチル環、シクロヘキシル環構造を有する基等が挙げられる。
前記炭素原子数2乃至20の分岐鎖状のアルケニル基としては、2-メチル-2-プロペニル基、イソプロペニル基、2-メチル-1-プロペニル基及び2-メチルアリル基等が挙げられる。
前記アリール基としては、フェニル基、ベンジル基、1-ナフチル基、2-ナフチル基、1-アントリル基及び1-フェナントリル基等が挙げられる。また、該アリール基は、置換基を有していてもよく、そのような置換基としては、エステル結合、アミド結合やエーテル結合を含んでもよい直鎖状、分岐状あるいは環状のアルキル基やハロゲン原子等が挙げられる。
また、疎水性有機溶媒に対して使用した際に離液することなく透明性の高いゲルを得ることができるという観点においては、R1はブチル基、ペンチル基、ヘキシル基であることが好ましい。
一方、親水性有機溶媒に対して使用した際に離液することなく透明性の高いゲルを得ることができるという観点においては、R1はオクチル基、デシル基、ドデシル基であることが好ましい。
さらには、親水性有機溶媒を含んでもよい水と油等の疎水性有機溶媒の両溶剤をそれぞれ単独に、もしくは両溶剤を混合させ均一性の高いゲルを得ることができるという観点においては、R1はプロピル基、ブチル基、ペンチル基であることが好ましい。
使用できる単糖としては、ピラノース環構造を示す単糖に限れば特に限定されるものではないが、アロース、アルトロース、グルコース、マンノース、グロース、イドース、ガラクトース及びタロース等が挙げられる。
その中でも、比較的安価で生体適合性が特に期待される観点から、単糖としては、グルコース及びマンノースが好ましい。
特に上記式(3)で表される化合物(グルコース型ゲル化剤)は、水と油(疎水性有機溶媒)のいずれにおいてもゲル形成能を有することを最大の特徴とし、水/油混合溶媒に対して水/油分散型ゲルを形成することができる。またアルコール系溶媒のゲル化を可能とし、水に対しては透明性の高いゲルを形成する。
一方、上記式(4)で表される化合物(マンノース型ゲル化剤)は、油(親水性有機溶媒および疎水性有機溶媒)に対して透明性の高いゲルを形成し得、チキソトロピー性に優れるゲルを得ることができる。そして自立可能(自己支持性を有する)である透明なゲルを形成できるという特性をも有する。
このように、グルコース型ゲル化剤とマンノース型ゲル化剤のゲル化能はそれぞれ特徴が異なり、それぞれの特徴に合わせた幅広い分野での適用を期待できる。
本発明のゲルは、上記ゲル化剤で溶媒をゲル化させることにより、得ることができる。具体的には、溶媒に所定量のゲル化剤を加熱溶解させ、冷却するという製造方法が例示される。通常、加熱溶解の際には、完全に溶解させることが好ましい。
なお、本明細書において、ゲル化とは、流動性のある液体が流動性を失った状態となることをいう。
溶媒をゲル化するに際し、本発明のゲル化剤の使用量は、本発明の効果を奏する限り特に限定されないが、ゲル化される溶媒の質量に対して通常20~0.001質量%、好ましくは2~0.05質量%である。
これらの中でも、前記疎水性有機溶媒としては、オリーブ油、ミリスチン酸イソプロピル、トルエン、シクロヘキサン、直鎖状シリコーン、環状シリコーン、アルキル変性シリコーン、フェニル変性シリコーン、ジメチコン又はジメチコノール等のシリコーン油及びオクタンが好ましい。
上記シリコーン油は、東レ・ダウコーニング(株)より入手し得る直鎖状シリコーン(商品名:2-1184)、環状シリコーン(商品名:SH245)、アルキル変性シリコーン(商品名:SS-3408)、フェニル変性シリコーン(商品名:PH-1555)、ジメチコン(商品名:BY-11-0シリーズ)、ジメチコノール(商品名:CB-1556)等を使用し得る。
前記アルコールは、好ましくは水に自由に溶解する水溶性アルコールであり、より好ましくは炭素原子数1乃至9のアルコール、多価アルコール、高級アルコール、グリセライド類が挙げられる。
具体的には、炭素原子数1乃至9のアルコールとしては、メタノール、エタノール、2-プロパノール、i-ブタノール、ペンタノール、ヘキサノール、1-オクタノール、イソオクタノール等;多価アルコールとしては、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等;高級アルコールとしては、オクチルドデカノール、ステアリルアルコール、オレイルアルコール等;グリセライド類としてはトリオクタノイン、トリ(カプリルカプリル酸)グリセリル、ステアリン酸グリセリル等が挙げられる。
これらの中でも、前記親水性有機溶媒としては、メタノール、エタノール、2-プロパノール、i-ブタノール、ペンタノール、ヘキサノール、1-オクタノール、イソオクタノール、アセトン、シクロヘキサノン、アセトニトリル、ジオキサン、グリセロール、プロピレングリコール、エチレングリコール及びジメチルスルホキシドが好ましく、グリセロール、プロピレングリコール及びエチレングリコールがより好ましい。
又、好ましい無機酸の例としては、塩酸、リン酸、炭酸、硫酸、硝酸及びホウ酸が挙げられる。より好ましくは、塩酸、リン酸、炭酸、硫酸であり、さらに好ましくは、塩酸、リン酸、炭酸である。
前記無機塩又は有機塩は、複数種を加えても良いが、好ましくは1又は2種である。塩を2種類加えることで、溶液が緩衝能をもつことも望ましい。
好ましい無機塩の例としては無機炭酸塩、無機硫酸塩、無機リン酸塩及び無機リン酸水素塩が挙げられる。より好ましくは、炭酸カルシウム、炭酸ナトリウム、炭酸カリウム、硫酸ナトリウム、硫酸カリウム、硫酸マグネシウム、リン酸カリウム、リン酸ナトリウム、リン酸水素二ナトリウム又はリン酸二水素ナトリウムであり、さらに好ましくは炭酸カルシウム、硫酸マグネシウム、リン酸水素二ナトリウム又はリン酸二水素ナトリウムである。
又、好ましい有機塩の例としては、無機酢酸塩、無機乳酸塩、無機クエン酸塩といった無機有機酸塩、有機アミンの塩酸塩若しくは有機アミン酢酸塩が挙げられる。より好ましくは、酢酸ナトリウム、酢酸カリウム、乳酸ナトリウム、乳酸カリウム、クエン酸ナトリウム、クエン酸カリウム、エチレンジアミン塩酸塩、エチレンジアミン四酢酸塩、トリスヒドロキシメチルアミノメタン塩酸塩である。
本発明のゲル化剤を、媒体である前述の疎水性有機溶媒、親水性有機溶媒、水、親水性有機溶液、疎水性有機溶液又は水溶液に加え、必要に応じて加熱撹拌して溶解させた後、室温に放置することにより、ゲルを得ることができる。ゲル強度は、ゲル化剤の濃度により調整することが可能である。
本発明の化粧品基材又は医療用基材は、上記ゲル化剤を含む。
また、本発明の化粧品基材又は医療用基材は、上記ゲル化剤の他に、水、アルコール、多価アルコール、親水性有機溶媒、疎水性有機溶媒、又はそれらの混合溶液を含むことができる。なお、前記アルコール、多価アルコール、親水性有機溶媒及び疎水性有機溶媒としては、前述のアルコール、多価アルコール、親水性有機溶媒及び疎水性有機溶媒で例示された化合物が挙げられる。
さらに、本発明の化粧品基材又は医療用基材は、必要に応じて、一般的に化粧品基材又は医療用基材に配合される生理活性物質及び機能性物質等の添加成分を含むことができ、そのような添加成分としては、油性基剤、保湿剤、感触向上剤、界面活性剤、高分子、増粘・ゲル化剤、溶剤、噴射剤、酸化防止剤、還元剤、酸化剤、防腐剤、抗菌剤、殺菌剤、キレート剤、pH調整剤、酸、アルカリ、粉体、無機塩、紫外線吸収剤、美白剤、ビタミン類及びその誘導体類、育毛用薬剤、血行促進剤、刺激剤、ホルモン類、抗しわ剤、抗老化剤、ひきしめ剤、冷感剤、温感剤、創傷治癒促進剤、刺激緩和剤、鎮痛剤、細胞賦活剤、植物・動物・微生物エキス、鎮痒剤、角質剥離・溶解剤、制汗剤、清涼剤、収れん剤、酵素、核酸、香料、色素、着色剤、染料、顔料、消炎剤、抗炎症剤、抗喘息、抗慢性閉塞性肺疾患、抗アレルギー、免疫調整剤、抗感染症剤及び抗真菌剤等が挙げられる。
前記高分子化合物としては、ゼラチン、アルギン酸ナトリウム、アルギン酸プロピレングリコール、アラビアゴム、ポリビニルアルコール、ポリアクリル酸、ポリアクリル酸ナトリウム、カルボキシメチルセルロース、ジェランガム、キサンタンガム、カラギーナンポリスチレン、ポリメチルメタアクリレート、ポリビニルピロリドン、ポリエチレンオキシド、ポリ乳酸、ポリスチレンスルホン酸、ポリアクリロニトリル、ポリエチレン及びポリエチレンテレフタレート等が挙げられる。
本発明のゲル電解質は、有機溶媒あるいは水からなる電解液(液体電解質)をゲル化して得られる。使用するゲル化剤と電解液は特に限定されるものではなく、使用に応じて適時選択すればよい。
例えば、前記有機溶媒からなる電解液の場合、非プロトン性有機溶媒の少なくとも1種に電解質塩を溶解させたものである。
前記非プロトン性有機溶媒としては、グライム、アルケンカーボネート、アルキルカーボネート、環状エーテル、アミド類、ニトリル類、ケトン類及びエステル類等が挙げられ、好ましい具体例として、プロピレンカーボネート、エチレンカーボネート、ジエチルカーボネート、γ-ブチロラクトン、1,2-ジメトキシエタン、テトラヒドロフラン、2-メチルテトラヒドロフラン、ジメチルスルホキシド、1,3-ジオキソラン、ホルムアミド、ジメチルホルムアミド、1,4-ジオキサン、アセトニトリル、ニトロメタン、エチルモノグライム、リン酸トリエステル、トリメトキシメタン、ジオキソラン誘導体、スルホラン、3-メチル-2-オキサゾリジノン、プロピレンカーボネート誘導体、テトラヒドロフラン誘導体、ジエチルエ-テル及び1,3-プロパンサルトン等が挙げられる。これらの有機溶媒は、単独で又は2種以上を組み合わせて使用することができる。
前記電解質塩は、カチオン金属と対アニオンからなり、カチオン金属としてはLi+、Na+、K+などが挙げられ、その対アニオンとしてはClO4 -、LiBF4 -、PF6 -、CF3SO3 -、CF3CO2 -、AsF6 -、SbF6 -、(CF3SO2)2N-、B10Cl10 2-、(1,2-ジメトキシエタン)2ClO4 -、低級脂肪族カルボン酸塩、AlCl4 -、Cl-、Br-、I-、クロロボラン化合物及び四フェニルホウ酸等が挙げられる。これらの中でも、好ましい電解質塩として、リチウム塩が挙げられる。これらの電解質塩は、単独で又は2種以上を組み合わせて使用することができる。
本発明はまた、前述の本発明のゲル化剤である式(1)又は式(2)で表される化合物を製造する方法も対象とする。
すなわち該製造方法は、下記式[A]
なお下記スキームA及びスキーム1~10に示す符号は、各々のスキーム内において付与された符号であり、発明の詳細な説明並びに特許請求の範囲において付した符号とは区別されるものである。
メチルα-D-マンノピラノシド、p-メトキシベンズアルデヒド、p-エトキシベンズアルデヒド、p-(ドデシルオキシ)ベンズアルデヒド、4-ブロモ-1-ブテン、1-ブロモ-3-メチル-2-ブテン,1-ブロモブタン、1-ブロモヘキサン、D(+)-グルコース、エチルα-D-グルコシドは和光純薬工業(株)より入手し、メチルα-D-グルコピラノシド、p-トルエンスルホン酸一水和物、4-プロポキシベンズアルデヒド、4-n-ブトキシベンズアルデヒド、4-n-ペンチルオキシベンズアルデヒド、4-n-ヘキシルオキシベンズアルデヒド、4-n-オクチルオキシベンズアルデヒド、4-n-デシルオキシベンズアルデヒド、オルトギ酸トリメチル、ブロモシクロヘキサン、ヨウ化テトラブチルアンモニウム、オルトギ酸トリエチル、4-ヒドロキシベンズアルデヒド、3-ヒドロキシベンズアルデヒド、バニリン、p-トルエンスルホン酸(無水物)、3,4-ジメトキシベンズアルデヒドは東京化成工業(株)より入手し、テトラフルオロホウ酸銅(II)水和物、2-エチルヘキシルブロミド、ゲラニルブロミドはシグマアルドリッチジャパン(株)より入手した。
また反応溶媒として使用したN,N-ジメチルホルムアミド(DMF)(脱水、有機合成用)、メタノール(脱水、有機合成用)およびエタノール(超脱水、有機合成用)は和光純薬工業(株)より入手した。
反応後処理および精製時に使用した硫酸ナトリウム(特級)、塩化ナトリウム(特級)、炭酸水素ナトリウム(特級)、ジエチルエーテル(特級)は和光純薬工業(株)より入手し、ヘキサン(特級)、酢酸エチル(特級)、クロロホルム(特級)、ジイソプロピルエーテル(特級)は関東化学(株)より入手した。
NMR測定用に使用した重クロロホルム(0.03%TMS(テトラメチルシラン)含有)および重ジメチルホルムアミドはシグマアルドリッチジャパン(株)より入手した。
オクタン(特級)、シクロヘキサン(特級)、トルエン(特級)、エタノール(特級)、オリーブ油、ミリスチン酸イロプロピル(一級)、グリセロール(特級)、スクアラン(一級)、スクアレン(特級)、アセトニトリル(特級)、メタノール(特級)、プロピレングリコール(特級)、1,3-ブタンジオール(別名:ブチレングリコール)(特級)、グリセリン(特級)は和光純薬工業(株)より入手し、エチレングリコール(特級)は関東化学(株)より入手し、SH245は東レ・ダウコーニング(株)より入手し、ペンチレングリコールはアイ・ティー・オー(株)より入手し、ジメチルスルホキシド(DMSO)は東京化成工業(株)より入手した。水は純水を使用した。
またゲル化試験において使用した防腐剤、界面活性剤は以下のとおりである。
防腐剤:メチルパラベン、2-フェノキシエタノール(特級)は和光純薬工業(株)より入手した。
界面活性剤:ポリオキシエチレンソルビタンモノラウレート(Tween20)、ドデシル硫酸ナトリウム(SDS、一級)、ステアリルトリメチルアンモニウムブロミド(STAB)、3-[(3-コールアミドプロピル)ジメチルアンモニオ]プロパンスルホネート(CHAPS)は和光純薬工業(株)より入手した。
(1)1H-NMRスペクトル
・装置:AVANCE500、ブルカー・バイオスピン(株)製
JNM-ECA 600、日本電子(株)製
(2)高速液体クロマトグラフィー(HPLC)
・装置:1200シリーズ、アジレント・テクノロジー(株)製
(3)LC-MS
・装置:e2695(LC)、2489(UV)、3100(MS)、日本ウォーターズ(株)製
(4)光学顕微鏡
・装置:DM2500、ライカマイクロシステムズ(株)製
(5)共焦点レーザースキャン顕微鏡
・装置:LSM700、カールツァイス(株)製
(6)走査型電子顕微鏡(SEM)
・装置:SU8000、日立ハイテクノロジーズ(株)製
(7)原子間力顕微鏡(AFM)
・装置:Nanocute、SIIナノテクノロジー(株)製
(8)ボルテックスミキサー
・装置:Voltex Genie 2、Scientific Industries社製
(9)ホモジナイザー
・装置:Omni TipTM Homogenizing Kit、Omni International社製
マンノース型ゲル化剤及びグルコース型ゲル化剤となる化合物は下記に示すスキームAに従って合成可能である。ゲル化剤の原料となる種々の炭化水素基を有する芳香族アルデヒド化合物は、市販されているものは購入により入手し(上述参照)、市販されていないものは後述するスキーム1に従って合成した。
また、芳香族アルデヒド化合物と糖の縮環反応は、アセタールを経由して縮環反応を実施するか、若しくはアルデヒドから加熱条件下で実施するのが一般的であるが、本発明は、芳香族アルデヒド化合物から室温下で、しかも一段階の縮環反応で得られることも特徴の一つとして挙げられる。
<金属触媒(テトラフルオロホウ酸銅(II)水和物)を用いたジメチルアセタール化(スキーム2)>
下記スキーム2に従い、芳香族アルデヒド化合物のジメチルアセタール化を実施し、アセタール誘導体〔17〕~〔32〕を得た。
下記スキーム4に従い、芳香族アルデヒド化合物のジエチルアセタール化を実施し、アセタール誘導体〔20’〕及び〔21’〕を得た。
<ジメチルアセタール誘導体からのマンノース型ゲル化剤の合成>
下記に示すスキーム5に従い、ジメチルアセタール誘導体にメチルα-D-マンノピラノシドを反応させ、マンノース型ゲル化剤として化合物〔M1〕~〔M10〕を合成した
下記に示すスキーム6に従い、ジメチルアセタール誘導体にメチルα-D-グルコピラノシドを反応させ、グルコース型ゲル化剤として化合物〔G1〕~〔G9〕及び〔G11〕~〔G13〕を合成した。
下記に示すスキーム7に従い、ジエチルセタール誘導体にメチルα-D-グルコピラノシドを反応させ、グルコース型ゲル化剤として化合物〔G3〕及び〔G4〕を合成した。
<メチル-α-D-グルコピラノシドを用いたグルコース型ゲル化剤の合成>
下記に示すスキーム8に従い、芳香族アルデヒド化合物から一段階にてグルコース型ゲル化剤として化合物〔G3〕及び〔G13’〕を合成した。
精製後のHPLCチャートおよび1H NMR(500MHz)をそれぞれ図1および図2に示す。HPLCでは2成分(保持時間2.16分、2.31分(溶媒:アセトニトリル/水=50/50))観測され、1H NMRからも2成分の存在が推定されたもののLC-MSにおいて目的物の分子イオンピーク(ESI-MS cald for C17H25O7[M+H]+ 341,found 341)が観測されたことからα体とβ体の混合物として目的物を得た。:収率32%。
実施例1で合成した化合物M1-M10、G1-G9、G11-G13をゲル化剤として、各種溶媒に対するゲル形成能(ゲル化能)並びに得られたゲルの各種評価を行った。同時に、公知物質(非特許文献1)として知られている化合物A:メチルα-D-4,6-ベンジリデンマンノース及び化合物B:メチルα-D-4,6-ベンジリデングルコースとのゲル化能の比較をそれぞれ行った。
ゲル化試験は次のように行った。4mLのねじ口サンプル管にゲル化剤および各種溶媒を加え、シクロヘキサン、アセトニトリル、メタノール、エタノール、エタノール/水混合溶媒では90℃、トルエン、水、DMSO/水混合溶媒では100℃、オクタン、SH245、オリーブ油、ミリスチン酸イソプロピル、エチレングリコール、グリセロールでは120℃で,それぞれ30分間加熱溶解させた。得られた溶液を室温にまで冷却し1時間放置してゲルの形成を観察した。なお、放冷後、溶液の流動性が失われて、サンプル管を倒置しても溶液が流れ落ちない状態を「ゲル化」と判断した。ゲル化試験はゲル化剤の濃度:2.0、1.0、0.5、0.25、0.1wt%で実施し、ゲル化に要するゲル化剤の最低濃度(wt%)を最低ゲル化濃度とした。ここで、濃度の単位を示すwt%は、wt/vol×100を意味する。得られた結果を表1及び表2に示す。表中の数字は最低ゲル化濃度(wt%)を表し、表中の符号は形成したゲルの状態を示し、透明なゲルは「G」、半透明なゲルは「#G」、濁ったゲルは「*G」、結晶化したものは「Cr」、部分的にゲル化したものは「PG」とした。またゲル化剤:2wt%の濃度でもゲル化しなかったものは「-」とした。
マンノース型ゲル化剤からなる各種ゲルのチキソトロピー性について評価した。チキソトロピー性試験は次のように行った。実施例2と同様に最低ゲル化濃度でのゲルを調製した。その後、ボルテックスミキサーを用いてゲルからゾル状態になるまで振盪させることによりゲルを崩壊させ、室温下、1時間静置した。1時間後、溶液が入ったサンプル管を倒置し、溶液が流れ落ちない状態のとき「チキソトロピー性がある」と判断した。得られた結果を表5に示す。なお表中は、チキソトロピー性があると判断したものを「○」、チキソトロピー性が無いと判断したものを「×」とし、ゲルを形成しないものは「-」とした。
実施例1で作製したマンノース型ゲル化剤:M1及びM3並びに公知物質である化合物Aを0.05wt%加えたSH245のゲルを室温にて7日放置した際のゲルの安定性を評価した。得られた結果を図3に示す。
図3に示すように、本発明のゲル化剤は、公知物質である化合物Aを用いたゲル化剤に比べて離液量が少なく、保存安定性に優れているとする結果を得た。また、ベンゼン環に結合する炭化水素基のアルキル鎖の鎖長が長くなるにつれ、離液量も少なくなることから、アルキル鎖長にゲルの保存安定性が大きく関与していることが示唆される結果を得た。
実施例2乃至実施例4に示すように、公知物質である化合物A及び化合物Bとの比較より、本発明のゲル化剤であるマンノース型ゲル化剤とグルコースゲル化剤がいずれも良好なゲル化能を有するとする結果を得た。また、アルキル鎖の導入によって、チキソトロピー性や保存安定性に優れるゲルを形成することが示唆される結果を得た。
これらの結果を受け、比較的極性溶媒に対して高いゲル化能を有することが示唆されたグルコース型ゲル化剤に関して、化粧品で配合される頻度の高い油剤(ミリスチン酸イソプロピル、オリーブオイル、SH245)及びアルコール(エタノール)配合水溶液に対するゲル化試験を行った。結果を表6に示す。ゲル化試験の条件は実施例2と同様に行った。
実施例5におけるアルコール配合試験より、各グルコース型ゲル化剤の配合可能なアルコール量が明らかになった。そこで、実施例3と同様に、アルコール配合水溶液ゲルのチキソトロピー性試験を行った。チキソトロピー性試験は次のように行った。まず、ゲル調製は実施例5と同様に、そして、チキソトロピー性試験は実施例3と同様に行った。このとき、ゲル化剤の濃度は最低ゲル化濃度から調製し、チキソトロピー性が発現するまで徐々に濃度を高く調製し、チキソトロピー性の発現を観察した。結果を表7に示す。表の枠内(下段)の数字はチキソトロピー性が発現したゲル化剤の濃度(wt%)を示し、( )内(上段)の数字及び記号は実施例5に示す最低ゲル化濃度及びゲルの状態を表している。なお公知物質である化合物Bは実施例2に示す結果を再掲した。設定したゲル化剤の濃度は、0.1、0.25、0.5、1.0、2.0wt%である。但し設定濃度範囲内でチキソトロピー性を発現しなかったものに関しては「×」と表記した。
一般に化粧品や医薬部外品には防腐剤や界面活性剤が配合される。本発明のゲル化剤において、防腐剤や界面活性剤を配合した場合におけるゲル可能について検討した。
防腐剤配合試験は次のように行った。所定の濃度になるように防腐剤を水に溶解させた防腐剤配合水溶液を調製した。その後、4mLのスクリュー管に所定濃度になるようにゲル化剤(グルコース型ゲル化剤:G3)を添加し、先に調製した防腐剤配合水溶液を加え、100℃で30分間加熱溶解させた。得られた溶液を室温にまで冷却し1時間放置して、スクリュー管を倒置させることによりゲルの形成を確認した。結果を表8に示す。用いた防腐剤は、メチルパラベン及びフェノキシエタノールそれぞれ単独のものと、それらを混合させたもので行った。
界面活性剤配合試験は次のように行った。所定の濃度になるように界面活性剤を水に溶解させた界面活性剤配合水溶液を調製した。その後、4mLのスクリュー管に所定濃度になるようにゲル化剤(グルコース型ゲル化剤:G3)を添加し、先に調製した界面活性剤配合水溶液を加え、100℃で30分間加熱溶解させた。得られた溶液を室温にまで冷却し1時間放置して、スクリュー管を倒置させることによりゲルの形成を確認した。結果を表9に示す。用いた界面活性剤は、ノニオン性の界面活性剤であるポリオキシエチレンソルビタンモノラウラート(Tween20)、アニオン性界面活性剤であるドデシル硫酸ナトリウム(SDS)、カチオン性界面活性剤であるステアリルトリメチルアンモニウムブロミド(STAB)及び両性界面活性剤である3-[(3-コールアミドプロピル)ジメチルアンモニオ]プロパンスルホネート(CHAPS)である。
化粧品のクリームやクレンジング剤において、油剤と水を均一に分散化、かつ安定化させるには、一般的に界面活性剤が使用されている。しかし、界面活性剤の配合は、皮膚への刺激や肌荒れの問題から、界面活性剤の配合量の低減が好まれている。
実施例7において、本発明のゲル化剤は界面活性剤配合時においても良好なゲルを形成するとする結果を得た。一方、実施例2及び実施例5に示すように、本発明のゲル化剤、特にグルコース型ゲル化剤:G1~G4は、水と油系溶媒のいずれもゲルを形成するとする結果を得ている。この結果は、本発明のゲル化剤が界面活性剤を用いずとも水と油を均一に分散化、かつ安定化させることが可能であることを示唆するものである。そこで、実施例8では、本発明のゲル化剤が水と油剤の両溶媒を均一に分散できるかどうかを確認すべく、水-油分散試験を行った。
水-油分散試験には、水と油剤の両方に対してゲル化能を有するG4と、油剤のみゲル化能を有するG5を用いた。これらゲル化剤の濃度は2.0、1.0、0.5、0.25、0.1wt%で実施した。
図5に示すように、G3についてもG4と同様に、最低ゲル化濃度が低く、かつ水と油の分散可能な配合割合の範囲が広く、良好な水/油分散ゲルを形成するとする結果を得た。さらに図6に示す共焦点レーザースキャン顕微鏡観察の結果より観測される液滴は約10~50μm程度であり、比較的に均一な大きさを有しているとする結果を得た。
実施例8における水-油分散試験では、ゲル化剤を溶媒に加熱溶解させた後に実施した撹拌にボルテックスミキサーを用いた。本実施例では、より高せん断の撹拌手段であるホモジナイザーを用いて水-油分散試験を実施した。ホモジナイザーにより高せん断を与えることにより、形成される液滴はより小さくなることが推測される。
実施例2~実施例9におけるゲル化試験並びに水-油分散試験は、ゲル化剤(化合物)粉末を各種溶媒に加えた後、加熱溶解させ各試験を実施したものである。この手法では、ゲル化剤粉末が各種溶媒に溶解するまでに時間を要する他、各種溶媒に対する溶解時間の違いから、汎用的な手法とは言い難い。仮に、粉末のゲル化剤を高濃度に溶解させた分散液を事前に調製し、その分散液を各種溶媒に添加することにより、ゲルもしくは水/油分散ゲルを迅速に調製することができれば、ゲル調製のプロセスの観点から迅速かつ簡便な手法であると考えられる。このようにゲル化剤の高濃度分散液を後から各種溶媒に添加し、ゲル、もしくは水/油分散ゲルを形成させる手法を、本明細書において「プレミックス」と定義する。本発明のゲル化剤においてプレミックスへの適用が可能であるかを判定すべくプレミックス試験を実施するために、まずゲル化剤を高濃度に溶解し得る分散液の検討を行った。
分散液に用いる溶媒の検討は次のように実施した。ゲル化剤(グルコース型ゲル化剤:G4)が所定の濃度(10wt%)になるように各種溶媒に加え、30分間ドライバス中で80~100℃にて加熱後、ゲル化剤の溶解の有無を確認し、1時間放冷させ室温に戻した。その後、プレミックス用分散液として使用可能かどうか確認するために、80℃での再溶解試験を実施した。分散液に使用した溶媒はエタノール(EtOH)、プロピレングリコール(PG)、ブチレングリコール(BG)、ペンチレングリコール(PenG)、グリセリン(Gly)のアルコール系溶媒を選択した。結果を表11に示す。
以上の結果より、分散液の溶媒として、再溶解可能であったプロピレングリコールを選択し、以下の手順に従いプレミックス試験を実施した。
プレミックス試験は次のとおり行った。まず、スクリュー管にミリスチン酸イソプロピル(21g)を加え、80℃で加熱した。その後、80℃に加熱した10wt%G4プロピレングリコール分散液(6.6g)を加え、均一溶液とした後、70℃で加熱した水(9g)を添加した。ホモジナイザーで10分間撹拌し、水/ミリスチン酸イソプロピル分散ゲルを調製した。
プレミックス試験後の最終組成を表12に示す。また図8に、水/ミリスチン酸イソプロピル分散ゲルの外観(図8(A))及び顕微鏡観察の結果(図8(B))を示す。
本発明のゲル化剤から調製されたゲルは、自立可能な固さを有するゲルであり、一方、せん断に対しては非常に弱く、液性を示し、せん断後は直ちに固まる特徴を有する。これらの特徴から、調製されたゲルは、容器から容易に取り出すことが可能であり、また鋭利な刃物で容易に切断し、切断後は離液することなくゲルの形状を維持し得る。
マンノース型ゲル化剤(M3)を用いたゲル取り出し試験は次のように行った。サンプル管に0.5wt%になるようにM3及びスクアレン(2.5mL)を添加後、130℃で30分間加熱溶解させ、1時間室温まで放冷することで、ゲルを調製した。その後、スパーテルを用いてゆっくりとゲルを取り出した。図9に、サンプル管より取り出したゲルの外観の写真を示す。図9(A)は取り出し直後、図9(B)は取り出したゲルをカバーガラス(厚さ:0.12-0.17mm)で切断したもの、図9(C)は切断したゲルを切断面同士で重ね合わせたものの写真である。
図9に示すように、取り出したゲルは自立可能(自己支持性)であり、またせん断後に離液することなくゲルの形状を維持し、また切断面同士で重ね合わせた場合に再接着可能であり、すなわち自己修復性を有し得るゲルであるとする結果を得た。
マンノース型ゲル化剤(M3)と同様に、グルコース型ゲル化剤であるG4を用いて、ゲル取り出し試験を行った。サンプル管に所定の濃度になるようにグルコース型ゲル化剤(G4)及び各種溶媒を添加後、120~130℃で30分間、加熱溶解させた。その後、その溶液(約2mL)を、立ててある円筒状の筒に流し込み、1時間室温まで放冷させることで、ゲルを調製した。円筒状の筒からゆっくりとゲルを押し出すことで、ゲルの取り出し試験を行った。結果を表13に示す。表中の記号は、取り出し後、ゲル形状を維持できたものは「○」、少し緩んでいるものは「△」、形状を維持できなかったものは「×」と判断した。また、未実施のものは斜線で示す。
実施例11の結果に示すように、本発明のゲル化剤から調製されたゲルは自立可能な固さを有するゲルであり、一方、せん断に対しては非常に弱く、液性を示し、せん断後は直ちに固まる特徴を有する。これらの特徴より、本発明のゲルが化粧品等で一般的に使用されるスプレー等の噴霧器において使用した場合に、均一な噴霧が期待でき、また噴霧後、直ちにゲル状となり、液だれすることなく良好な塗布特性を有することが期待される。
トルエンのゾルーゲル相転移温度(Tgel)を測定した。測定は、マンノース型ゲル化剤(M1~M6、M8)又は公知物質の化合物Aとトルエンにて調製したゲルが入ったサンプル管を、温度制御されたドライバス中に入れ25℃で5分間静置した後、ドライバスからサンプル管を取り出し、倒置してゲルが溶液となり下方に落ちるか確認した。ゲルの状態を維持していたときはドライバスを30℃に設定し、ゲルが入ったサンプル管を入れて5分間静置した後、同様の操作を行った。以上の操作を繰り返しドライバスを5℃ずつ昇温していき、サンプル管を倒置してゲルが溶液となり下方に落ちた温度をTgelとした。図10に各ゲル化剤のトルエンゲルにおけるゲル化剤の濃度に対するゾルーゲル相転移温度(Tgel)を示す。
同様の試験により、溶媒をSH245に変更し、最低ゲル化濃度にて調製したSH245ゲルにおけるゲル化剤の濃度とゾルーゲル相転移温度(Tgel)を表15に示す。
また、表15に示すように、公知物質である既知のゲル化剤化合物Aと比較して、ゲル化剤M1~M6およびM8を用いて得たSH245ゲルはゾル-ゲル相転移温度が高いとする結果を得た。このことは既知の化合物Aと比較し、本発明のゲル化剤が熱的に安定なゲルが調製可能なことを示すものである。
実施例1で調製したマンノース型ゲル化剤:M2又は公知物質の化合物Aを1wt%加えたトルエンゲルを調製した後、このゲルを24時間真空乾燥させることにより得られたキセロゲルを走査型顕微鏡(SEM)にて観察した。得られた結果を図11に示す。
図11に示すSEM画像より、ゲル化剤Aのトルエンゲル(キセロゲル)では幅がおよそ500nmから800nmのファイバー状の像が得られたのに対し、ゲル化剤M2のトルエンゲル(キセロゲル)では板状の像が得られた。
実施例14のSEM像において確認された本発明のゲル化剤より得られたトルエンゲル(キセロゲル)における板状体の詳細な情報を確認すべく、AFM像の観察を行った。
実施例1で合成したマンノース型ゲル化剤:M2(0.02wt%)又はM6(0.02wt%)を加えたトルエン溶液を100℃にて加熱調製し、これをグラファイト基板(HOPG)上にキャストした後、1時間静置後24時間真空乾燥し、HOPGを原子間力顕微鏡(AFM)にて観察した。得られた結果を図12に示す。なお図12には、最低ゲル化濃度(M2:0.5wt%、M6:2wt%)でゲル化させたゲルの外観写真も合わせて示す。
図12に示すAFM画像より、ゲル化剤M2のトルエン溶液から調製したゲル(キセロゲル)はHOPGからの高さが約3.5nmのファイバー構造を有しているとみられる結果を得た。この結果より、実施例13のSEM画像で見られたゲル化剤M2の板状体は、幅約3.5nmのファイバー構造がバンドル化して板状になっているとみられる。
また、ゲル化剤M2とM6のトルエン溶液から調製したゲル(キセロゲル)をAFMにより比較観察すると、M2のトルエン溶液から調製したゲル(キセロゲル)では高さが約3.5nmのファイバー構造を形成しているのに対し、M6のトルエン溶液から調製したゲル(キセロゲル)では高さが3.1nmから3.8nmのファイバーがバンドル化し、テープ状構造を形成しているとみられる結果を得た。
実施例1で作製したマンノース型ゲル化剤:M2を0.5wt%加えたトルエンゲル及び0.1wt%加えた水ゲルを調製し、それぞれ24時間凍結乾燥させることにより得られたキセロゲルをSEMにて観察した。得られた結果を図13に示す。
図13に示すSEM画像より、トルエンゲル(キセロゲル)はファイバーがバンドル化した板状体であったのに対し、水ゲル(キセロゲル)は幅約200nmのファイバー構造を形成しているとする結果を得た。
実施例1で作製したマンノース型ゲル化剤:M2又はグルコース型ゲル化剤:G3を0.1wt%加えた水ゲルを調製し、24時間凍結乾燥させることにより得られたキセロゲルをSEMにて観察した。得られた結果を図14に示す。
図14に示すSEM画像より、M2を用いた水ゲル(キセロゲル)は幅約200nmのファイバー構造を形成しているのに対し、G3を用いた水ゲル(キセロゲル)は幅約40から50nmのファイバー構造を形成しているとする結果を得た。
このように、水ゲルにおいて、ゲル化剤の糖部分の構造をマンノースからグルコースに変えることでゲルの透明性が高まること、そして各々のゲル化剤からなるファイバー構造の幅が細くなる傾向にあるとする結果となった。
Claims (20)
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤と、疎水性有機溶媒、親水性有機溶媒、水、親水性有機溶液、疎水性有機溶液又は水溶液よりなるゲル。
- 前記疎水性有機溶媒は植物油、エステル類、シリコーン油及び炭化水素類からなる群から選択される少なくとも一種である、請求項4に記載のゲル。
- 前記親水性有機溶媒はメタノール、エタノール、2-プロパノール、i-ブタノール、ペンタノール、ヘキサノール、1-オクタノール、イソオクタノール、アセトン、シクロヘキサノン、アセトニトリル、ジオキサン、グリセロール、プロピレングリコール、エチレングリコール及びジメチルスルホキシドからなる群から選択される少なくとも一種である、請求項4に記載のゲル。
- 前記親水性有機溶液は請求項6に記載の親水性有機溶媒と水との混合溶媒である、請求項4に記載のゲル。
- 前記疎水性有機溶液は請求項5に記載の疎水性有機溶媒と水との混合溶媒である、請求項4に記載のゲル。
- 前記水溶液は有機酸、又は、無機酸、又は、無機炭酸塩、無機硫酸塩、無機リン酸塩及び無機リン酸水素塩からなる群から選択される少なくとも一種の無機塩、又は、酢酸塩、乳酸塩、クエン酸塩、有機アミン塩酸塩及び有機アミン酢酸塩からなる群から選択される少なくとも一種の有機塩を溶解させた水溶液である、請求項4に記載のゲル。
- 前記有機酸が酢酸、クエン酸、コハク酸、乳酸、リンゴ酸、マレイン酸、フマル酸及びトリフルオロ酢酸からなる群から選択される少なくとも一種の有機酸であり、前記無機酸が塩酸、リン酸、炭酸、硫酸、硝酸及びホウ酸からなる群から選択される少なくとも一種の無機酸であり、前記無機塩が、炭酸カルシウム、炭酸ナトリウム、炭酸カリウム、硫酸ナトリウム、硫酸カリウム、硫酸マグネシウム、リン酸カリウム、リン酸ナトリウム、リン酸水素二ナトリウム及びリン酸二水素ナトリウムからなる群から選択される少なくとも一種の無機塩であり、前記有機塩が、酢酸ナトリウム、酢酸カリウム、乳酸ナトリウム、乳酸カリウム、クエン酸ナトリウム、クエン酸カリウム、エチレンジアミン塩酸塩、エチレンジアミン四酢酸塩及びトリスヒドロキシメチルアミノメタン塩酸塩からなる群から選択される少なくとも一種の有機塩である、請求項9に記載のゲル。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、化粧品基材又は医療用基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤及び少なくとも1種の高分子化合物を含む、化粧品基材又は医療用基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、ゲル電解質。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、細胞培養基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、生体分子保存用基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、外用基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、生化学用基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、食品用基材。
- 請求項1乃至請求項3のうち何れか1項に記載のゲル化剤を含む、乾燥地農業用基材。
- 請求項1に記載の式(1)又は式(2)で表される化合物を製造する方法において、
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017034005A1 (ja) * | 2015-08-25 | 2017-03-02 | 日産化学工業株式会社 | オイルゲル化剤による高含水率エマルションゲルの調製法 |
WO2017034004A1 (ja) * | 2015-08-25 | 2017-03-02 | 国立大学法人九州大学 | 新規糖誘導体ゲル化剤 |
WO2017099232A1 (ja) | 2015-12-11 | 2017-06-15 | 国立大学法人静岡大学 | オイルゲル化剤 |
JP2022536428A (ja) * | 2020-06-04 | 2022-08-17 | 雲南中煙工業有限責任公司 | 可逆的相転移特性を有する霧化液ゲル、その製造方法、及び使用 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104478847B (zh) * | 2014-12-10 | 2016-08-24 | 天津大学 | 缩醛取代的葡萄糖酰胺及制备方法及制备超分子凝胶的方法 |
WO2018002947A1 (en) * | 2016-06-30 | 2018-01-04 | Hindustan Petroleum Corporation Ltd. | C5 sugar based gelators for oil spills |
EP3496698A1 (de) | 2016-08-09 | 2019-06-19 | Symrise AG | Mischungen enthaltend (e)-3-benzo[1,3]dioxol-5-yl-n,n-diphenyl-2-propenamid |
CN108492989A (zh) * | 2018-03-01 | 2018-09-04 | 成都理工大学 | 一种基于胆固醇衍生物的准固态电解质的制备方法 |
CN112142805B (zh) * | 2020-09-09 | 2022-03-25 | 江南大学 | 一种n-烷基葡萄糖胺小分子醇凝胶及其制备方法和应用 |
CN113363603A (zh) * | 2021-06-07 | 2021-09-07 | 南开大学 | 一种用于水系可充锌电池的弱酸性电解液添加剂及其应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0363224A (ja) * | 1989-08-02 | 1991-03-19 | Kureha Chem Ind Co Ltd | プロトカテキュアルデヒド類の糖誘導体 |
JPH03218390A (ja) * | 1989-08-18 | 1991-09-25 | Basf K & F Corp | 新規な環状アセタールならびにこれを含有する喫煙組成物及び食品 |
JPH10265761A (ja) | 1997-03-24 | 1998-10-06 | Jsr Corp | オイルゲル化剤 |
JPH11323309A (ja) * | 1998-03-13 | 1999-11-26 | Japan Science & Technology Corp | 糖ベンジリデン誘導体から成るゲル化剤 |
JP2000256303A (ja) | 1999-03-11 | 2000-09-19 | Ajinomoto Co Inc | 液状有機媒体のゲル化又は固化剤 |
JP2004359643A (ja) | 2003-06-09 | 2004-12-24 | Kyowa Hakko Chemical Co Ltd | リジン誘導体及びゲル化剤 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01139519A (ja) * | 1987-11-24 | 1989-06-01 | Kanebo Ltd | 皮膚刺激を抑制した化粧料 |
WO2002096921A1 (fr) | 2001-05-30 | 2002-12-05 | Nisshin Seifun Group Inc. | Nouveau derive glucose induisant l'apoptose, procede de production et utilisation comme medicament |
ITMI20060530A1 (it) * | 2006-03-22 | 2007-09-23 | Univ Milano Bicocca | Antinfiammatori a struttura monosaccaridica |
FR2934998B1 (fr) * | 2008-08-12 | 2010-09-03 | Robert Vachy | Nouveaux derives de glucopyranose, leur preparation et leurs applications biologiques |
CN101735284B (zh) * | 2008-11-24 | 2012-05-23 | 上海医药工业研究院 | 一种4,6-o-苄叉-d-吡喃葡萄糖的制备方法 |
-
2013
- 2013-03-08 CN CN201380013053.0A patent/CN104159992B/zh active Active
- 2013-03-08 US US14/383,654 patent/US9278989B2/en active Active
- 2013-03-08 KR KR1020147026154A patent/KR102073769B1/ko active IP Right Grant
- 2013-03-08 WO PCT/JP2013/056493 patent/WO2013133419A1/ja active Application Filing
- 2013-03-08 CN CN201610635933.7A patent/CN106349299B/zh active Active
- 2013-03-08 JP JP2014503563A patent/JP6347742B2/ja active Active
- 2013-03-08 EP EP13757549.4A patent/EP2824157B1/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0363224A (ja) * | 1989-08-02 | 1991-03-19 | Kureha Chem Ind Co Ltd | プロトカテキュアルデヒド類の糖誘導体 |
JPH03218390A (ja) * | 1989-08-18 | 1991-09-25 | Basf K & F Corp | 新規な環状アセタールならびにこれを含有する喫煙組成物及び食品 |
JPH10265761A (ja) | 1997-03-24 | 1998-10-06 | Jsr Corp | オイルゲル化剤 |
JPH11323309A (ja) * | 1998-03-13 | 1999-11-26 | Japan Science & Technology Corp | 糖ベンジリデン誘導体から成るゲル化剤 |
JP2000256303A (ja) | 1999-03-11 | 2000-09-19 | Ajinomoto Co Inc | 液状有機媒体のゲル化又は固化剤 |
JP2004359643A (ja) | 2003-06-09 | 2004-12-24 | Kyowa Hakko Chemical Co Ltd | リジン誘導体及びゲル化剤 |
Non-Patent Citations (2)
Title |
---|
MARLON F.ABREU ET AL.: "Tuning methyl 4,6-0- benzylidene a-D-glucopyranosides'gelation ability by minor group modifications", CARBOHYDRATE RESEARCH, vol. 353, 3 April 2012 (2012-04-03), pages 69 - 78, XP055161660 * |
S. SHINKAI ET AL., CHEM. EUR. J., vol. 7, no. 20, 2001, pages 4327 - 4334 |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2017034004A1 (ja) * | 2015-08-25 | 2018-08-30 | 国立大学法人九州大学 | 新規糖誘導体ゲル化剤 |
US10544181B2 (en) | 2015-08-25 | 2020-01-28 | Kyushu University | Sugar derivative gelators |
CN108350012B (zh) * | 2015-08-25 | 2021-11-05 | 国立大学法人九州大学 | 新的糖衍生物胶凝剂 |
CN108350012A (zh) * | 2015-08-25 | 2018-07-31 | 国立大学法人九州大学 | 新的糖衍生物胶凝剂 |
US20180280296A1 (en) * | 2015-08-25 | 2018-10-04 | Nissan Chemical Industries, Ltd. | Method for preparing high-water-content emulsion gel using oil gelling agent |
JPWO2017034005A1 (ja) * | 2015-08-25 | 2018-08-23 | 日産化学株式会社 | オイルゲル化剤による高含水率エマルションゲルの調製法 |
WO2017034004A1 (ja) * | 2015-08-25 | 2017-03-02 | 国立大学法人九州大学 | 新規糖誘導体ゲル化剤 |
WO2017034005A1 (ja) * | 2015-08-25 | 2017-03-02 | 日産化学工業株式会社 | オイルゲル化剤による高含水率エマルションゲルの調製法 |
EP3838250A1 (en) | 2015-08-25 | 2021-06-23 | Kyushu University | Novel sugar derivative gelators |
US10640462B2 (en) | 2015-12-11 | 2020-05-05 | National University Corporation Shizuoka University | Oil gelator |
KR20180093898A (ko) | 2015-12-11 | 2018-08-22 | 닛산 가가쿠 가부시키가이샤 | 오일겔화제 |
WO2017099232A1 (ja) | 2015-12-11 | 2017-06-15 | 国立大学法人静岡大学 | オイルゲル化剤 |
JP2022536428A (ja) * | 2020-06-04 | 2022-08-17 | 雲南中煙工業有限責任公司 | 可逆的相転移特性を有する霧化液ゲル、その製造方法、及び使用 |
JP7198919B2 (ja) | 2020-06-04 | 2023-01-04 | 雲南中煙工業有限責任公司 | 可逆的相転移特性を有する霧化液ゲル、その製造方法、及び使用 |
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EP2824157B1 (en) | 2020-02-12 |
CN106349299B (zh) | 2019-09-27 |
KR20140138748A (ko) | 2014-12-04 |
EP2824157A1 (en) | 2015-01-14 |
CN104159992B (zh) | 2017-03-08 |
CN104159992A (zh) | 2014-11-19 |
US9278989B2 (en) | 2016-03-08 |
JP6347742B2 (ja) | 2018-06-27 |
JPWO2013133419A1 (ja) | 2015-07-30 |
KR102073769B1 (ko) | 2020-02-05 |
EP2824157A4 (en) | 2015-11-18 |
CN106349299A (zh) | 2017-01-25 |
US20150025157A1 (en) | 2015-01-22 |
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