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WO2011115314A1 - Effet antioxydant de nanodiamant fonctionnel et utilisation associée - Google Patents

Effet antioxydant de nanodiamant fonctionnel et utilisation associée Download PDF

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Publication number
WO2011115314A1
WO2011115314A1 PCT/KR2010/001688 KR2010001688W WO2011115314A1 WO 2011115314 A1 WO2011115314 A1 WO 2011115314A1 KR 2010001688 W KR2010001688 W KR 2010001688W WO 2011115314 A1 WO2011115314 A1 WO 2011115314A1
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Prior art keywords
antioxidant
nanodiamond
group
formula
compound
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Ceased
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PCT/KR2010/001688
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English (en)
Korean (ko)
Inventor
이민영
지아영
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NANODIAMOND Inc
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NANODIAMOND Inc
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Priority to PCT/KR2010/001688 priority Critical patent/WO2011115314A1/fr
Publication of WO2011115314A1 publication Critical patent/WO2011115314A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0007—Organic substances
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm
    • 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
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the present invention relates to functional nanodiamonds, and more particularly, to an antioxidant composed of surface functionalized nanodiamond compounds prepared by chemically modifying the surface of nanodiamonds.
  • the antioxidant effect on nanodiamonds is not known yet.
  • the present invention relates to functional nanodiamonds, a new concept of antioxidant, which is not known until now.
  • Oxidation of substances not only causes various diseases in vivo, but also causes aging and is known to shorten the life of many industrial materials.
  • Antioxidants or antioxidants are compounds that inhibit or delay the automatic oxidation of a substance. Antioxidants are classified into preventive antioxidants, primary antioxidants and secondary antioxidants according to their mechanism of action. Prophylactic antioxidants are compounds that prevent the production of free radicals, which are literally the source of antioxidants. Primary antioxidants are chain-breaking antioxidants that quickly eliminate free radicals or peroxy radicals already produced. Secondary antioxidants do not have anti-oxidative effects on their own, but they are also known as antioxidant synergists as compounds that increase antioxidant activity by coexisting with free radical inhibitors.
  • Antioxidants can also be divided into natural and synthetic antioxidants.
  • Vitamin C, tocopherol, natural ascorbic acid, polyphenols, and various plant extracts are used as natural antioxidants, and BHA (butylhydroxyanisole) and butylhydroxytoluene (BHT), which are phenolic compounds, are representatively used as synthetic antioxidants.
  • antioxidants that are chemically synthesized are rarely used. Recently, due to the rapid development of nanotechnology, researches to use nanoparticles such as gold, silver and platinum as antioxidants have been activated, but they are still in the research and development stage due to various problems.
  • the first object of the present invention is to prepare a surface functionalized nanodiamond compound maximized antioxidant effect and to measure their antioxidant effect by the ORAC method.
  • a second object of the present invention is to use the nanodiamond compound as an antioxidant additive such as water, beverages, alcoholic beverages, food, cosmetics, pharmaceutical raw materials, oils and fats, and to prevent oxidation of paints, polymers, ceramics, and metals will be.
  • an antioxidant consisting of surface functionalized nanodiamond compounds represented by the following formula (I) or salts thereof.
  • Formula I ND- (R) n , where n is an integer of 2 or greater.
  • ND represents a nanodiamond single particle, and a plurality of R each represent a moiety chemically bonded to the surface of the nanodiamond, wherein R represents an amine group (NH 2 ), a hydroxyl group (OH), It has a chemical structure containing at least one or more selected from the group consisting of a carboxyl group (COOH), and combinations thereof.
  • R represents an amine group (NH 2 ), a hydroxyl group (OH), It has a chemical structure containing at least one or more selected from the group consisting of a carboxyl group (COOH), and combinations thereof.
  • R may be represented by Formula II.
  • X is a linker for covalently linking an amine group to a nanodiamond surface, and includes a group consisting of one or more methylene groups, carboxyl groups, ether groups, amide groups, ester groups, and combinations thereof. It includes one selected from.
  • R may further include a food nutritional or pharmaceutically acceptable salt of Formula II.
  • the antioxidant may be used in one selected from the group consisting of water, beverages, alcoholic beverages, and coffee to exhibit antioxidant, antioxidant, or antioxidant enhancement effects.
  • the antioxidant may be used as a food additive to exhibit antioxidant, antioxidant, or antioxidant enhancement effects.
  • the antioxidant may be used as a cosmetic raw material to exhibit an antioxidant, antioxidant, or antioxidant enhancement effect.
  • the antioxidant may be used as a pharmaceutical composition to exhibit antioxidant, antioxidant, or antioxidant enhancement effects.
  • the antioxidant may be used in tobacco to exhibit antioxidant, antioxidant, or antioxidant enhancement effects.
  • the antioxidant may be used in one selected from the group consisting of soap, shampoo, detergent, bathing articles and can exhibit an antioxidant, antioxidant, or antioxidant enhancement effect.
  • the antioxidant may be used to prevent rancidity of edible fats and oils or industrial oils.
  • the antioxidant can be used as an additive in animal feed.
  • the antioxidant can be used as an additive to preserve the grain.
  • the antioxidant may be used to prevent oxidation of one selected from the group consisting of flowers, fruits, vegetables, meat, poultry, and fish.
  • the antioxidant may be used to prevent one oxidation selected from the group consisting of plastics, rubber, adhesives, fibers, polymer film, and polymer coating agent.
  • the antioxidant may be used to prevent oxidation of one bulk or surface selected from the group consisting of ceramic materials, metal materials, and composite materials in combination thereof.
  • the nanodiamond compounds of the present invention show excellent dispersibility in the liquid phase, so that they can be used as additives in drinking water, beverages, alcohol, food, cosmetics, medicine, coating materials, structural materials, etc. Can be used to show antioxidant effects.
  • Figure 7 Fluorescence attenuation graph according to the concentration of the sample.
  • Nanodiamonds are attracting attention as new nanomaterials because they are not only physically and chemically stable but also have no biotoxicity.
  • particles having a size of 10 nm or less are specifically defined as ultrananocrystalline diamond (UNCD), and their application range is rapidly spreading.
  • UNCD is an ultrafine diamond crystal with a relatively uniform particle size distribution of about 5 nm in diameter, and is mainly synthesized by explosive explosion.
  • due to the problem of dispersibility it has been used in a limited range, and various methods of modifying the surface have been proposed to overcome this problem.
  • nanodiamonds of several nanometers in size can attach a large amount of various functional groups to the surface of nanodiamonds through various chemical synthesis methods in gas phase or liquid phase.
  • the antioxidant effect of such functional nanodiamonds has not been published yet.
  • FRAP ferric reducing / antioxidant power
  • TEAC trolox equivalent antioxidant capacity
  • ORAC oxygen radical absorbance capacity
  • FRAP and TEAC use single electron transfer and ORAC uses hydrogen atom transfer. Since FRAP and TEAC were not developed based on the mechanism of the chain reaction, it is difficult to measure antioxidant activity. Based on the mechanisms that control antioxidant chain reactions, ORAC was first developed in 1993 by researchers at the National Institute of Aging under the NIH, and has since been recognized as a gold standard method of measuring antioxidant effects.
  • Antioxidant effect measurement method using ORAC protocol is as follows.
  • Disodium fluorescein (FL) one of the fluorescent dyes, is fluoresced by the bleaching effect in the presence of an oxidizing agent.
  • Mixing samples that are expected to have an antioxidant effect on the solution prevents the oxidation of FL, resulting in longer fluorescence. That is, the intensity of the fluorescence is reduced when the fluorescent material is oxidized by the oxidizing agent.
  • the presence of antioxidants in the solution decreases the rate of destruction of the fluorescent material and increases the fluorescence intensity.
  • the lower area is calculated from the attenuation curve graph obtained by measuring the intensity of the fluorescence as a function of time.
  • AAPH 2,2'-azobis (2-amidinopropane) dihydrochloride
  • the value obtained by comparing the degree of oxidative destruction of fluorescence with the standard antioxidant Trolox is the ORAC value.
  • a standard curve is created using different Trolox concentrations and then compared to the sample. The final result is expressed as Trolox Equivalent (TE).
  • TE Trolox Equivalent
  • ORAC experiments were performed for the purpose of using functionally-modified nanodiamonds chemically modified on the surface of nanodiamonds as antioxidants or antioxidants.
  • ORAC experiments were performed on pristine nanodiamonds, which showed a certain level of antioxidant effect despite the high dispersibility.
  • the degree of antioxidant effect of functional nanodiamonds depends on the type of functional groups attached to the surface, especially nanodiamonds having a moiety attached to amine groups (hereinafter referred to as aminated nanodiamonds) exhibit the best antioxidant effects. Appeared.
  • These antioxidant nanodiamonds may be applied to various fields such as food, cosmetics, medicine, agriculture, petrochemicals, polymers, ceramics and metals.
  • FIG. 1 is a schematic diagram of one of the nanodiamond (ND) compounds having an amine group.
  • the central portion of the schematic diagram represents nanodiamonds, and amine groups are attached to the surface in large amounts by covalent bonds.
  • the aminated nanodiamond compound is synthesized from the pristine nanodiamond in a liquid phase through a multi-step manufacturing process as shown in various examples below.
  • These functionalized nanodiamonds show excellent dispersibility compared to pristine nanodiamonds, and have a very high antioxidant effect, i.e., an ORAC index.
  • ND- (COOH) n compound 100 mg was added to 30 mL of BH 3 / THF, followed by sonication for 1 hour, followed by the same filtration and drying process as in Example 1, where a plurality of moieties including hydroxyl groups were present on the surface of the nanodiamond. Obtain ND- (CH 2 OH) n attached.
  • ND- (COOH) n powder 100 mg was dissolved in 50 mL of ethylenediamine, and then 50 mg HATU reagent was added and sonicated for 4 hours to prepare nanodiamonds having an amide group.
  • the reaction was diluted with 200 mL of methanol, filtered and dried to obtain ND- (CONHCH 2 CH 2 NH 2 ) n compound powder having a plurality of moieties including amide groups and amine groups on the surface of nanodiamonds. .
  • ND- (CH 2 OH) n powder 100 mg was sonicated in 30 ml THF for 30 minutes to introduce an amine group (NH 2 ) to the nanodiamond surface.
  • 10 mg of diethylazodicarboxylate coupling agent and 50 mg of phthalimide were added thereto, sonicated for 2 hours, 300 mL of methanol was poured out, diluted, filtered and dried.
  • This powder was placed in 50 mL of trifluoroacetic acid (TFA), sonicated for 3 hours, filtered and dried to provide ND- (CH 2 NH 2 ) n powder having a plurality of moieties containing amine groups on the surface of nanodiamonds.
  • TFA trifluoroacetic acid
  • the surface modification of the surface functionalized ND compounds was analyzed by making samples in the form of KBR pellets using FTIR (Varian).
  • the strong peaks appearing at 1670 cm ⁇ 1 in the spectrum of the ND- (COOH) n compound of FIG. 2 are due to C ⁇ O stretching.
  • the C ⁇ O stretching peak disappears and peaks appear at 2923 cm ⁇ 1 and 2845 cm ⁇ 1 , showing the CH stretching oscillation mode in the methylene group.
  • the IR spectrum of the ND- (CONHCH 2 CH 2 NH 2 ) n compound shows a CN stretching oscillation mode at 1030 cm ⁇ 1 .
  • the vibration mode corresponding to carbonyl stretching appears at 1679 cm -1 .
  • the ND- (CH 2 NH 2 ) n compound has an in-plane bending mode of amine group at 1624 cm ⁇ 1 and an out-of-plane bending mode at 737 cm ⁇ 1 .
  • Figure 3 shows the particle size distribution of pristine nanodiamonds and aminated nanodiamonds in aqueous solution.
  • the measurement for the particle size analysis was performed using a dynamic light scattering device (Scatteroscope, Qudix).
  • Pristine nanodiamonds show a bimodal pattern with average particle diameters of 16 nm and 20 ⁇ m, indicating that a large number of nanodiamonds are aggregated in the liquid phase.
  • nanodiamonds have an average particle diameter of 8 nm, showing that they are distributed as single particles without forming aggregates in aqueous solution.
  • the chemical modification of the surface of the nanodiamond has the effect of providing the nanodiamond with excellent dispersibility as well as chemical functionality.
  • Table 1 shows the pH of the aqueous solution measured in the concentration range of ND- (CH 2 NH 2 ) n 0.001 to 10 ⁇ M.
  • ND- (CH 2 NH 2 ) n 0.001 to 10 ⁇ M As a molecular weight value of the nanodiamond required for the concentration calculation, 100,000, which is a value calculated in consideration of the particle size, was used.
  • the pH of the aqueous solution is not linearly proportional to the log 10 value of the ND- (CH 2 NH 2 ) n concentration, which is a typical characteristic of the weakly basic solute.
  • the results shown in Table 1 indicate that the aminated nanodiamonds can be added to water, liquor, or food to increase the pH, and can be used to convert acidic or neutral water into weakly alkaline if necessary. For example, adding 10 mg of aminated nanodiamonds to 1 L of neutral water can produce an aqueous solution of acidity close to 7.4, the physiological pH value.
  • ORAC assay was carried out by the following method. Fluorescence measurement was performed using a fluorescence spectrophotometer (F-4500, Hitachi). The excitation and fluorescence wavelengths were 480 nm and 520 nm, respectively, and all experiments were performed at room temperature.
  • fluorescein (FL) was dissolved in 1 ml of phosphate buffer at pH 7.4 to make 70 ⁇ M of stock solution. This stock solution was stored in the dark and diluted with 70 nM of solution prior to measurement. 0.1356 g of 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPH) was dissolved in phosphate buffer to form a 50 mM aqueous solution. 5 mM Trolox stock solution was prepared by dissolving 0.0125 g of Trolox in 10 mL of phosphate buffer. It was diluted to 1 ⁇ 5 ⁇ M and used to calculate trolox calibration curve.
  • AAPH 2,2'-azobis (2-amidinopropane) dihydrochloride
  • the calibration curve of trolox was measured after incubation of FL solution (240 ⁇ L), AAPH (240 ⁇ L), and trolox (120 ⁇ L) for 10 minutes at 37 ° C. That is, after measuring the fluorescence intensity over time of the buffer solution of FL and AAPH, a series of fluorescence attenuation graphs of the solution in which the trolox solution is mixed to 5 ⁇ M at 1 ⁇ M intervals are obtained in series.
  • the final total solution used for fluorescence measurement was 600 ⁇ L and the fluorescence intensity was measured up to 3,600 seconds (60 minutes) at 25 second intervals.
  • FL solution (240 ⁇ L), AAPH (240 ⁇ L), and antioxidant solution (120 ⁇ L) were mixed and incubated at 37 ° C. for 10 minutes to measure fluorescence for 60 minutes.
  • Blank was measured after incubation of a mixture of buffer (120 ⁇ L), fluorescein solution (240 ⁇ L), and AAPH (240 ⁇ L) at 37 ° C. for 10 minutes.
  • AUC was calculated using the following equation after peak normalization of all fluorescence attenuation graphs to calculate the area under curve (AUC) of the fluorescence attenuation graph.
  • f 0 is the fluorescence intensity at time 0 and n is the number of data for obtaining the fluorescence attenuation graph.
  • the relative ORAC value (Trolox equivalent) from the AUC is calculated by the following equation.
  • ORAC [(AUC sample -AUC blank ) / (AUC sample -AUC blank )]
  • FIG. 4 shows a FL fluorescence attenuation graph according to trolox concentration
  • FIG. 5 is a trolox calibration curve calculated therefrom.
  • x is the trolox concentration ( ⁇ M)
  • y is the AUC.
  • the correlation coefficient (R 2 ) is above 0.99, indicating a very satisfactory level.
  • FIG. 6 is a graph showing fluorescence attenuation of pristine nanodiamonds.
  • the molecular weight value of the pristine diamond required for the concentration calculation 100,000 was calculated based on the size of the nanoparticles.
  • the AUCs were calculated for each of the concentration ranges from 1 to 5 ⁇ M from FIG. 6 and the average value of the relative ORAC values obtained therefrom was 5.2.
  • pristine nanodiamonds exhibit antioxidant effects, they appear to be mainly due to the radical scavenging function of the surface sp 2 structure, but the detailed mechanism is not yet known.
  • Figure 7 shows the fluorescence attenuation graph of vitamin C, clove, surface functionalized nanodiamonds. Since the antioxidant effect of vitamin C is well known, it was selected as a control. Clove was selected for relative comparison because it is known to have the highest ORAC level among natural products known to date. For the relative comparison of their antioxidant levels, a graph of fluorescence attenuation of each sample, especially at 5 ⁇ M, is shown in FIG. 8. At this concentration, the aminated nanodiamond shows little change in fluorescence intensity for 60 minutes and remains constant. 9 shows the AUC of each sample by measurement concentration.
  • Table 2 shows the ORAC values calculated by the above formula for each concentration, and their average values are also shown. Although the molecular weight of the nanodiamond may be slightly changed through surface functionalization, 100,000, which is the same value as the pristine nanodiamond, was used to maintain consistency.
  • Figure 10 shows the ORAC index of vitamin C, clove and functional nanodiamonds. Aminized nanodiamonds exhibited 25-fold antioxidant activity at the same concentrations as compared to vitamin C and also showed higher ORAC values than cloves.

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Abstract

L'invention concerne un antioxydant ou un inhibiteur d'oxydation obtenu au moyen d'un composé nanodiamant fonctionnalisé. Ledit composé comprend des nanoparticules résultant de la modification chimique des surfaces des nanodimants. L'effet antioxydant a été mesuré par le procédé du pouvoir absorbant des radicaux oxydants (ORAC). Il est en outre confirmé que le composé possède un effet antioxydant global, bien qu'il existe quelque variation en fonction de la structure chimique de la partie qui est liée chimiquement à la surface du nanodiamant. Plus précisément, un composé de nanodiamant ayant un groupe amine présente une valeur ORAC qui correspond à 25 fois le niveau de la vitamine C à la même concentration d'eau. Le composé de nanodiamant renforce les propriétés antioxydantes de l'eau, des boissons gazeuses, des boissons alcoolisées, des aliments, des cosmétiques, des produits médicinaux, des graisses alimentaire/huiles ou des grains, ou que l'on peut utiliser afin de prévenir l'oxydation des huiles industrielles, des polymères, des céramiques ou des métaux. (Figure 7).
PCT/KR2010/001688 2010-03-18 2010-03-18 Effet antioxydant de nanodiamant fonctionnel et utilisation associée Ceased WO2011115314A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140076348A (ko) * 2012-12-12 2014-06-20 기초과학연구원 세리아 나노입자를 포함하는 산화방지제
KR20160063529A (ko) * 2014-11-26 2016-06-07 나노리소스 주식회사 항산화 나노다이아몬드, 이의 제조방법 및 이를 포함하는 조성물
PL424917A1 (pl) * 2018-03-16 2019-09-23 Politechnika Koszalińska Sposób modyfikacji antyoksydacyjnych powierzchni opakowań poprzez rozpylanie zawiesiny wodnej detonacyjnych nanocząstek diamentowych
PL424918A1 (pl) * 2018-03-16 2019-09-23 Politechnika Koszalińska Zastosowanie warstw antyoksydacyjnych z naniesionymi detonacyjnymi nanodiamentami na opakowania wybranych produktów spożywczych, wyrobów kosmetycznych, preparatów farmaceutycznych oraz suplementów diety

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20040105096A (ko) * 2003-06-04 2004-12-14 (주)우인나노텍 나노 다이아몬드가 첨가된 주방기구용 코팅재, 이를이용한 주방기구 및 그 제조방법
JP2007119265A (ja) * 2005-10-25 2007-05-17 Nanocarbon Research Institute Co Ltd ナノダイヤモンド組成物とその製造方法
JP2007238411A (ja) * 2006-03-10 2007-09-20 Naoki Komatsu ナノダイヤモンド
KR20080093625A (ko) * 2007-04-17 2008-10-22 현대자동차주식회사 나노 다이아몬드 입자를 이용한 수지 코팅 방법
KR20090037774A (ko) * 2007-10-13 2009-04-16 나노다이아몬드 주식회사 표면 기능화를 통해 제조된 나노다이아몬드 화합물
KR20100099795A (ko) * 2009-03-04 2010-09-15 이화여자대학교 산학협력단 기능성 나노다이아몬드의 항산화 효과 및 그 응용

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20040105096A (ko) * 2003-06-04 2004-12-14 (주)우인나노텍 나노 다이아몬드가 첨가된 주방기구용 코팅재, 이를이용한 주방기구 및 그 제조방법
JP2007119265A (ja) * 2005-10-25 2007-05-17 Nanocarbon Research Institute Co Ltd ナノダイヤモンド組成物とその製造方法
JP2007238411A (ja) * 2006-03-10 2007-09-20 Naoki Komatsu ナノダイヤモンド
KR20080093625A (ko) * 2007-04-17 2008-10-22 현대자동차주식회사 나노 다이아몬드 입자를 이용한 수지 코팅 방법
KR20090037774A (ko) * 2007-10-13 2009-04-16 나노다이아몬드 주식회사 표면 기능화를 통해 제조된 나노다이아몬드 화합물
KR20100099795A (ko) * 2009-03-04 2010-09-15 이화여자대학교 산학협력단 기능성 나노다이아몬드의 항산화 효과 및 그 응용

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140076348A (ko) * 2012-12-12 2014-06-20 기초과학연구원 세리아 나노입자를 포함하는 산화방지제
KR20160063529A (ko) * 2014-11-26 2016-06-07 나노리소스 주식회사 항산화 나노다이아몬드, 이의 제조방법 및 이를 포함하는 조성물
KR102383798B1 (ko) 2014-11-26 2022-04-07 나노리소스 주식회사 항산화 나노다이아몬드 제조방법 및 이를 포함하는 조성물
PL424917A1 (pl) * 2018-03-16 2019-09-23 Politechnika Koszalińska Sposób modyfikacji antyoksydacyjnych powierzchni opakowań poprzez rozpylanie zawiesiny wodnej detonacyjnych nanocząstek diamentowych
PL424918A1 (pl) * 2018-03-16 2019-09-23 Politechnika Koszalińska Zastosowanie warstw antyoksydacyjnych z naniesionymi detonacyjnymi nanodiamentami na opakowania wybranych produktów spożywczych, wyrobów kosmetycznych, preparatów farmaceutycznych oraz suplementów diety

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