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WO2018135200A1 - Composition comprenant un groupe hydrophobe et des saccharides - Google Patents

Composition comprenant un groupe hydrophobe et des saccharides Download PDF

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Publication number
WO2018135200A1
WO2018135200A1 PCT/JP2017/045097 JP2017045097W WO2018135200A1 WO 2018135200 A1 WO2018135200 A1 WO 2018135200A1 JP 2017045097 W JP2017045097 W JP 2017045097W WO 2018135200 A1 WO2018135200 A1 WO 2018135200A1
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WIPO (PCT)
Prior art keywords
powder composition
fullerene
composition according
water
hydrophobic
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Ceased
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PCT/JP2017/045097
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English (en)
Japanese (ja)
Inventor
瑞希 坂田
平田　修
鷹行 井本
畑中　大輔
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Nissan Chemical Corp
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Nissan Chemical Corp
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Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Publication of WO2018135200A1 publication Critical patent/WO2018135200A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/152—Fullerenes
    • C01B32/156—After-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00

Definitions

  • the present invention relates to a composition for water-solubilizing or water-dispersing a hydrophobic cluster, particularly fullerene, and a method for producing the composition.
  • the hydrophobic cluster described here is a hydrophobic organic substance or inorganic substance that cannot generally be dispersed / dissolved in water, and atoms or molecules aggregate through van der Waals force, hydrogen bond, covalent bond, etc. Refers to an aggregate of fine particles of several nanometers to several hundred nanometers.
  • hydrophobic organic substances such as ⁇ -conjugated compounds such as conductive polymers, conjugated cyclic compounds, carotenoids, carbon materials such as carbon nanotubes, fullerenes, graphene, graphite, carbon black, carbon atoms and heteroatoms
  • carbon clusters such as boron atoms and carbolines such as carbolines, metal oxides, and inorganic inorganic particles such as hydrophobic inorganic substances are applied to basic research and practical application in the fields of electronic materials, pharmaceuticals, foods, cosmetics and daily necessities. Have been widely studied.
  • fullerene a kind of carbon allotrope along with diamond, graphene, graphite, and carbon nanotube, has attracted attention in the fields of electronic materials, pharmaceuticals, foods, cosmetics and daily necessities due to its unique chemical structure and electronic properties. .
  • Fullerene is a hydrophobic carbon cluster having a hollow structure in which many carbon atoms are bonded in a cage shape.
  • fullerene (Cn, n: number of carbon atoms) is a molecular chemical species having a molecular weight.
  • C 70 , C 74 , C C Higher order fullerenes such as 76 and C 78 have been reported so far.
  • solubility medium fullerenes is very low, good its solubility with respect to a limited organic solvents are solvents high and difficult to say (for example, the solubility of C 60 fullerene, toluene; 2.9 mg / mL, benzene; 1.5 mg / mL, carbon tetrachloride; 0.32 mg / mL, N-methyl-2-pyrrolidone; 0.89 mg / mL, polyethylene glycol; 0.004 mg / mL, dimethyl sulfoxide; 0.001 mg / mL, ethanol; 0.001 mg / mL), and solubility in water is extremely low ( ⁇ 0.00001 mg / mL) (see, for example, Patent Document 1). At present, the solubility of fullerenes in a medium and low storage stability are major issues in application development.
  • a method for producing a fullerene aqueous dispersion in which fullerene is saturated and dissolved in a relatively good polar organic solvent (for example, dimethyl sulfoxide or tetrahydrofuran), water is added, and then the solvent is removed if necessary.
  • a relatively good polar organic solvent for example, dimethyl sulfoxide or tetrahydrofuran
  • water is added, and then the solvent is removed if necessary.
  • the aqueous dispersion contains an organic solvent and that an organic solvent having a boiling point lower than that of water must be used to remove the organic solvent.
  • Patent Documents 5 and 6 polysaccharides or oligosaccharides that form inclusion complexes with fullerenes are selected, and there are no reports on polysaccharides, oligosaccharides, or sugar alcohols that do not form inclusion complexes. .
  • JP 2005-60380 A Special table 2013-528582 JP 2001-348214 A JP 2007-70147 A International Publication No. 2011/066541 JP 2006-69812 A
  • the present invention has been made in view of the above problems, and provides a composition comprising a hydrophobic cluster having water solubility or water dispersibility sufficient for practical use, and a method for producing the composition.
  • the present invention is as follows: (1) A water-soluble or water-dispersible powder composition comprising a powder obtained by dry-grinding a mixture of hydrophobic clusters and saccharides. (2) The powder composition according to the above (1), wherein the ratio (by weight) of the hydrophobic cluster to the saccharide is in the range of 1: 100 to 1: 1. (3) The powder composition according to either (1) or (2) above, wherein the saccharide is a polysaccharide, an oligosaccharide or a sugar alcohol. (4) The powder composition according to (3), wherein the polysaccharide is selected from the group consisting of chitosan, xanthan gum, hydroxymethylcellulose, calcium alginate, ⁇ -carrageenan and pectin.
  • a method for producing a water-soluble or water-dispersible powder composition comprising dry pulverizing a mixture comprising hydrophobic clusters and saccharides to obtain a powder.
  • the powder composition of the present invention can be uniformly dissolved or dispersed in an aqueous medium without requiring selection based on the particle size and specific gravity of fullerene in the preparation process. Furthermore, a solid gel can also be formed by increasing the concentration of the powder composition in the aqueous medium or adding metal ions.
  • the aqueous fullerene dispersion obtained from the powder composition of the present invention can have a high concentration (for example, 10 to 1000 ppm) that is not comparable to that obtained by conventional techniques, and has excellent long-term stability. .
  • the powder composition of the present invention includes a powder obtained by dry-grinding a mixture of hydrophobic clusters and saccharides, and is characterized by being water-soluble or water-dispersible.
  • the water dispersibility means that the powder composition of the present invention is added to an aqueous medium, and after stirring by overturning, the powder composition is visually dispersed well, and after standing at room temperature for 1 day, preferably 1 After standing for a week, it means that there are no aggregates visually.
  • a hydrophobic cluster-containing aqueous composition described later obtained from the powder composition of the present invention is allowed to stand at room temperature for 1 day, more preferably for 1 week, and then a filter having a pore size of 0.45 ⁇ m (material is regenerated cellulose) Is preferable).
  • hydrophobic cluster in the present invention is an organic or inorganic substance that is usually insoluble or low in dispersibility in water, and is formed by aggregation of atoms or molecules through van der Waals force, hydrogen bond, covalent bond, or the like. Means an aggregate of nanometer to hundreds of nanometer particles.
  • hydrophobic organic materials include ⁇ -conjugated compounds and the like
  • hydrophobic inorganic materials include carbon clusters, metal oxides, inorganic fine particles, and the like.
  • ⁇ -conjugated compound is a general term for compounds having delocalized electrons by alternately locating single bonds and multiple bonds in the compound.
  • ⁇ -conjugated compounds are known to reduce the energy of the whole molecule and increase the stability. Unshared electron pairs, radicals, carbenium ions, etc. are also considered as part of the conjugated system.
  • ⁇ -conjugated compounds include conductive polymers such as polyphenylene, polyphenylene vinylene, polythiophene, polyethynylene, polydiacetylene, polyacetylene, polypyrrole, polyfuran, polyaniline; porphyrin, pentacene, naphthacene, pyrene, anthracene, naphthalene, benzene, Conjugated cyclic compounds such as annulene, azulene, cyclopentadiene; cinnam alcohol, cinnamaldehyde, orthophenylphenol, butylhydroxyanisole, butylhydroxytoluene, flavonoids (eg, catechin), nicotinic acid, nicotinamide, ⁇ -tocopherol, Aromatic compounds which may contain heteroatoms such as nitrogen, oxygen and sulfur atoms such as coumarin and salicylic acid; and ⁇ -carotene, retino
  • carbon clusters include carbon nanotubes such as single-walled carbon nanotubes or multi-walled carbon nanotubes, carbon materials such as fullerene, graphene, graphite (graphite), activated carbon, carbon black, furnace black, acetylene black, and ketjen black. It is done. These may contain hetero atoms such as nitrogen atom, oxygen atom, sulfur atom and boron atom, and specific examples thereof include boron clusters such as carborane and carboline composed of carbon atom and boron atom. Among these, carbon nanotubes such as single-walled carbon nanotubes and multi-walled carbon nanotubes, fullerene, graphene, graphite, and carbon black are preferable, and fullerene is particularly preferable.
  • the fullerene used in the present invention is a fullerene having 60 to 120 carbon atoms, preferably 60, 70, 76, 78, 80, 82, 84, 86, 88, 90, 92, 94, 96 fullerenes.
  • the carbon atom in the fullerene hollow structure is modified with another functional group, the hollow structure includes an ionic species, and the hollow structure is partially ring-opened.
  • the fullerene is not particularly limited, but fullerene having 60 and 70 carbon atoms (that is, C 60 fullerene and C 70 fullerene) or a mixture thereof is more preferable, and fullerene having 60 carbon atoms (that is, C 60 fullerene). Is most preferred.
  • the fullerene used in the present invention may include carbon materials other than fullerene such as graphite and other powder materials as impurities.
  • a fullerene containing 20% by mass or more, preferably 70% by mass or more, more preferably 90% by mass or more can be used.
  • saccharide used as a dispersant for the hydrophobic cluster in the present invention include polysaccharides, oligosaccharides, and sugar alcohols.
  • Polysaccharide is a general term for substances in which a number of monosaccharide molecules are linked by glycosidic bonds.
  • starch amylose, amylopectin, pectin, alginic acid, alginate (eg, calcium alginate), alginate (eg, propylene glycol alginate), glycogen, guar gum, dextran, and celluloses (eg, methylcellulose, hydroxymethylcellulose) , Hydroxyethylcellulose, hydroxyethylmethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose), carrageenan (eg, ⁇ -carrageenan), caraya gum, carboxymethyldextran, agar, xanthan gum, chitin, chitosan, chondroitin sulfate, mucopolysaccharide
  • chitosan and xanthan gum Hydroxymethyl cellulose, calcium alginate, .kappa. is preferably selected from carrageenan and pectin, chitosan, xanthan gum, and especially preferably selected
  • the oligosaccharide of the present invention means an oligomer in which several monosaccharide molecules are linked by glycosidic bonds, and the number of monosaccharide molecules is from 2 to 10 sugars, preferably from 2 to 8 sugars. It is as follows. Specific examples include sucrose, cyclodextrin, trehalose, lactose, oligohyaluronic acid, maltose, and hydrolyzed polysaccharides, among which oligohyaluronic acid or trehalose is preferable.
  • UniqSens SFE System unique sense SFE system, natural emulsifier consisting of pectin / xanthan gum / carrageenan
  • CP KELCO unique sense SFE system, natural emulsifier consisting of pectin / xanthan gum / carrageenan
  • the ratio (by weight) of hydrophobic clusters to saccharides is in the range of 1: 100 to 1: 1.
  • the ratio (by weight) of fullerene to saccharide is in the range of 1: 100 to 1: 1, preferably in the range of 1:50 to 1: 2, and more preferably 1 : The range is 25 to 1: 3.
  • the dry grinding conditions for the mixture of hydrophobic clusters and saccharides are not particularly limited as long as the hydrophobic clusters and saccharides can be pulverized into small pieces, but the mortar, ball mill, pot mill, crusher, cutter mill, homogenizer, It is desirable to use a pulverizer such as a bead shocker, pin mill, jet mill, hybridization, extruder or mass collider.
  • a pulverizer such as a bead shocker, pin mill, jet mill, hybridization, extruder or mass collider.
  • the pulverization time and the treatment pressure are appropriately adjusted according to the hardness of the hydrophobic cluster and saccharide to be pulverized.
  • the ball mill, pot mill, crusher, multi-bead shocker, hybridization, extruder or masco is effective in that the dispersibility of fullerene in the resulting composition is improved under the conditions of dry pulverization in a mixture of fullerene and saccharide. Dry crushing is preferably performed using a Royder.
  • the average particle size of the dry pulverized powder can be determined, for example, by the scattering intensity average particle size by a dynamic light scattering device (DLS) in an aqueous medium.
  • the average particle diameter is 1 ⁇ m or less, preferably 500 nm or less, more preferably 300 nm or less.
  • the lower limit value of the average particle diameter is, for example, 10 nm.
  • a hydrophobic cluster-containing aqueous composition can be obtained by dissolving or dispersing the powder composition of the present invention in an aqueous medium. Since the hydrophobic cluster-containing aqueous composition of the present invention can uniformly disperse a high concentration of hydrophobic clusters in an aqueous medium and has excellent long-term stability, the field of electronic materials, pharmaceuticals, foods, cosmetics and daily necessities Can be used. The concentration of the hydrophobic cluster contained in the aqueous composition of the present invention is appropriately set according to the properties of the powder composition.
  • the concentration is 10 ppm to 1000 ppm, preferably 10 ppm to 500 ppm, more preferably 10 ppm to 300 ppm, It is preferably 10 ppm to 200 ppm, particularly preferably 10 ppm to 100 ppm.
  • the aqueous medium is water, a water-miscible organic solvent or a mixture thereof, preferably water or a mixture of water and a water-miscible organic solvent.
  • water miscible organic solvents include alcohols having 1 to 4 carbon atoms such as methanol, ethanol, isopropyl alcohol and butanol, ketones such as acetone, nitriles such as acetonitrile, N-methylpyrrolidone, N-cyclohexylpyrrolidone Amides such as N, N-dimethylacetamide and N, N-dimethylformamide, lactones such as ⁇ -butyrolactone, and ethers such as tetrahydrofuran. These are appropriately selected according to the purpose of the hydrophobic cluster-containing aqueous composition of the present invention, and can be contained within a range that does not adversely affect the dissolution or dispersion of the hydrophobic clusters.
  • the hydrophobic cluster-containing aqueous composition of the present invention may contain other components depending on the purpose.
  • any other component can be added as long as it does not adversely affect the dissolution or dispersion of fullerene or astaxanthin.
  • examples of such other components include alcohols, polyhydric alcohols, sugars, emollients, nonionic surfactants, plant extracts, water-soluble polymers, fragrances, colorants, UV protection agents, pH adjusters. , Antiseptics, bactericides, antioxidants, sequestering agents and bioactive ingredients.
  • blend a dispersing agent, a thickener, or surfactant suitably for melt
  • ⁇ Crusher No. 18D manufactured by Ishikawa Factory Co., Ltd.
  • Dynamic light scattering device DLS: manufactured by Malvern Instruments Ltd, Zetasizer Nano ZS ⁇ Viscometer: A & A Co., tuning fork type (SV type) viscometer
  • Hybridization Nara Machinery Co., Ltd.
  • Extruder Nara Machinery Co., Ltd.
  • Multi-Bead Shocker Yasui Instrument Co., Ltd.
  • Mascoloider Masuyuki Sangyo Co., Ltd.
  • oligohyaluronic acid manufactured by Kewpie Co., Ltd.
  • trehalose manufactured by Hayashibara Co., Ltd.
  • chitosan manufactured by Koyo Chemical Co., Ltd.
  • xanthan gum manufactured by Sansho Co., Ltd.
  • hydroxypropyl Cellulose manufactured by Nippon Soda Co., Ltd.
  • Metrose hydroxypropylmethylcellulose type
  • Dispersion test A dispersion test of C 60 fullerene powder compositions obtained in Examples 1 to 6 and Comparative Examples 1 to 5 in water was performed. The test method, the powder composition of the C 60 fullerene to a predetermined concentration shown in Table 2 was added to water, after inclining-stirring to obtain an aqueous dispersion. The obtained aqueous dispersion was allowed to stand overnight, and the dispersion state was visually confirmed.
  • Examples 7 to 15 Preparation of powder composition C 60 fullerene (manufactured by Sigma-Aldrich CO. LLC.) And dispersant are weighed according to Table 3, and dry pulverized and mixed together (16200 rpm) by hybridization (manufactured by Nara Machinery Co., Ltd.). 3 to 10 minutes) to obtain a powder composition of C 60 fullerene of Examples 7 to 15.
  • ⁇ -carrageenan manufactured by Sanki Co., Ltd.
  • mannitol manufactured by Junsei Chemical Co., Ltd.
  • oligohyaluronic acid manufactured by Kewpie Co., Ltd.
  • trehalose manufactured by Hayashibara Co., Ltd.
  • Xanthan gum KELTROL registered trademark
  • CG-SFT manufactured by Sanki Co., Ltd.
  • Examples 16 to 17 (1) Preparation of powder composition Weigh C 60 fullerene (manufactured by Sigma-Aldrich CO. LLC.) And dispersant according to Table 4 and dry-grind and mix together with an extruder (manufactured by Nara Machinery Co., Ltd.). The treatment (75 rpm, 5 passes) was performed, and the powder compositions of C 60 fullerene of Examples 16 and 17 were obtained.
  • sugars disersing agents
  • xanthan gum KELTROL registered trademark
  • CG-SFT manufactured by Sanki Co., Ltd.
  • pectin manufactured by Sanki Co., Ltd.
  • Examples 18 to 29, Comparative Example 6 (1) Preparation of powder composition C 60 fullerene (manufactured by Sigma-Aldrich CO. LLC.) And dispersant are weighed according to Table 5, and dry pulverized and mixed together with a multi-bead shocker (manufactured by Yasui Kikai Co., Ltd.). The treatment (26000 rpm, 4 minutes) was carried out to obtain a C 60 fullerene powder composition of Examples 18 to 29.
  • Examples 30 to 31 (1) Preparation of powder composition C 60 fullerene (manufactured by Sigma-Aldrich CO. LLC.) And dispersant are weighed according to Table 6, and dry pulverized and mixed with a mass colloider (manufactured by Masuko Sangyo Co., Ltd.) together. (15000 rpm, 5 passes) to obtain a powder composition of C 60 fullerene of Examples 30 to 31.
  • Examples 32 to 39 (1) Preparation of powder composition According to Table 7, astaxanthin (manufactured by Wako Pure Chemical Industries, Ltd.) and polysaccharide (dispersant) are weighed together and dry pulverized together with a multi-bead shocker (manufactured by Yasui Kikai Co., Ltd.). A mixing process (2700 rpm, 30 seconds, 2 minutes, 3 minutes) was performed to obtain an astaxanthin powder composition.
  • xanthan gum As sugars (dispersing agents), xanthan gum (KELTROL (registered trademark) CG-SFT; manufactured by Sanki Co., Ltd.) and pectin (GENU (registered trademark) LM-104AS-J; manufactured by Sanki Co., Ltd.) were used. .
  • Dispersion test A dispersion test of the powder composition of astaxanthin obtained in Examples 32 to 39 in water was performed. As the test method, each astaxanthin powder composition was added to water so as to have a predetermined concentration described in Table 7, and after stirring by overturning, an aqueous dispersion was obtained. The obtained aqueous dispersion was allowed to stand overnight, and the dispersion state was visually confirmed. In each aqueous dispersion, the powder composition of astaxanthin is visually dispersed: ⁇ : well dispersed and highly transparent; ⁇ : suspended and dispersed; ⁇ : dispersed but aggregated over time; x: completely dispersed Without defining it. The results are shown in Table 7.
  • the method for producing the water-soluble or water-dispersible powder composition of the present invention is very simple, and there is no need to perform complicated processes such as filtration, centrifugation, sediment removal, and distillation operation, and the hydrophobic composition is efficiently hydrophobic.
  • a cluster (particularly fullerene or astaxanthin) -containing aqueous composition can be obtained, which is characterized by being dispersible in water.
  • the dispersible hydrophobic cluster can be applied to a wide range of concentrations, so that it can be used in various industrial fields such as electronic materials, pharmaceuticals and daily necessities.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nanotechnology (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne : une composition de poudre soluble dans l'eau ou dispersible dans l'eau comprenant une poudre obtenue par broyage à sec d'un mélange comprenant un groupe hydrophobe et des saccharides ; et son procédé de production.
PCT/JP2017/045097 2017-01-17 2017-12-15 Composition comprenant un groupe hydrophobe et des saccharides Ceased WO2018135200A1 (fr)

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JP2017-006153 2017-01-17
JP2017006153A JP2020037489A (ja) 2017-01-17 2017-01-17 疎水性クラスター及び糖類を含む組成物

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Cited By (5)

* Cited by examiner, † Cited by third party
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WO2019117224A1 (fr) * 2017-12-15 2019-06-20 日産化学株式会社 Antioxydant comprenant un agrégat hydrophobe et des saccharides
CN110342499A (zh) * 2019-07-26 2019-10-18 广西科学院 一种生物质高温碳化末端微氧烧蚀制备类富勒烯碳球的方法
JP2020125256A (ja) * 2019-02-04 2020-08-20 日清紡ホールディングス株式会社 疎水性アルギン酸粒子群及びその製造方法
CN113522363A (zh) * 2021-06-29 2021-10-22 北京科技大学 水凝胶中金属离子改性mof微/纳结构的制备方法及应用
EP3848014A4 (fr) * 2018-08-02 2022-08-10 Beijing Fullcan Biotechnology Co., Ltd Composition topique de fullerène soluble dans l'eau

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CN111547706B (zh) * 2020-05-11 2022-12-06 赤峰福纳康生物技术有限公司 一种脱除富勒烯溶剂残留的方法

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019117224A1 (fr) * 2017-12-15 2019-06-20 日産化学株式会社 Antioxydant comprenant un agrégat hydrophobe et des saccharides
EP3848014A4 (fr) * 2018-08-02 2022-08-10 Beijing Fullcan Biotechnology Co., Ltd Composition topique de fullerène soluble dans l'eau
JP2020125256A (ja) * 2019-02-04 2020-08-20 日清紡ホールディングス株式会社 疎水性アルギン酸粒子群及びその製造方法
CN110342499A (zh) * 2019-07-26 2019-10-18 广西科学院 一种生物质高温碳化末端微氧烧蚀制备类富勒烯碳球的方法
CN113522363A (zh) * 2021-06-29 2021-10-22 北京科技大学 水凝胶中金属离子改性mof微/纳结构的制备方法及应用
CN113522363B (zh) * 2021-06-29 2022-11-15 北京科技大学 水凝胶中金属离子改性mof微/纳结构的制备方法及应用

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