WO2007110924A1 - Procede d'inhibition d'oxydation utilisant un composant volatil - Google Patents

Procede d'inhibition d'oxydation utilisant un composant volatil Download PDF

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Publication number
WO2007110924A1
WO2007110924A1 PCT/JP2006/306264 JP2006306264W WO2007110924A1 WO 2007110924 A1 WO2007110924 A1 WO 2007110924A1 JP 2006306264 W JP2006306264 W JP 2006306264W WO 2007110924 A1 WO2007110924 A1 WO 2007110924A1
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WO
WIPO (PCT)
Prior art keywords
substituent
oily component
antioxidant
absorbance
alkyl
Prior art date
Application number
PCT/JP2006/306264
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English (en)
Japanese (ja)
Inventor
Teruo Miyazawa
Kiyotaka Nakagawa
Jun Kariya
Original Assignee
Tohoku University
Project M Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tohoku University, Project M Co., Ltd. filed Critical Tohoku University
Priority to PCT/JP2006/306264 priority Critical patent/WO2007110924A1/fr
Priority to JP2008507311A priority patent/JPWO2007110924A1/ja
Publication of WO2007110924A1 publication Critical patent/WO2007110924A1/fr

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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
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen

Definitions

  • the present invention evaluates the oxidation prevention method using volatilized phenolic compounds, the antioxidant containing the phenolic compounds, and the antioxidant ability of the test substance in the volatile state. On how to do.
  • Antioxidants include natural antioxidants such as ascorbic acid (vitamin C), tocopherol (vitamin E) and flavonoids, and synthetic antioxidants such as butylhydroxylazole (BHA) and dibutylhydroxytoluene (BHT).
  • vitamin C ascorbic acid
  • vitamin E tocopherol
  • flavonoids synthetic antioxidants
  • BHA butylhydroxylazole
  • BHT dibutylhydroxytoluene
  • Ascorbic acid is a water-soluble compound and is difficult to use in oil and fat foods.
  • Tocopherol needs to be used in combination with other anti-oxidant agents that have a very high anti-acid power.
  • Flavonoids are colored and have limited use.
  • Synthetic acid inhibitors, such as BHA and BHT are a safety issue and their use in foods and pharmaceuticals is restricted. against this background, the development of excellent antioxidants to replace conventional antioxidants is desired!
  • An object of the present invention is to provide a method for preventing oxidation that is excellent in antioxidative power, safe and versatile.
  • the present inventors have found that an excellent anti-oxidative effect is exhibited by using a phenolic compound in a volatilizable state. The present invention has been completed.
  • the present invention includes the following inventions.
  • a method for preventing acidification which comprises allowing a phenolic compound to coexist with a target substance in a volatilizable state.
  • a phenolic compound is represented by the following formula I:
  • R 1 may have a substituent, may be C alkyl or have a substituent! /, May! /, C
  • R 2 may have a hydrogen atom or a substituent, or may have C alkyl or a substituent! /
  • R 3 to R 5 are each independently a hydrogen atom or a substituent
  • the antioxidant method according to (1) which is a compound represented by the formula:
  • the phenolic compound is at least one selected from the group forces of guaiacol, bulguaiacol, eugenol, isoeugenol and 2,4,6-trimethylphenol (1) to (3 ) The method for preventing acidification according to any of the above.
  • R 1 may have a substituent, may be C alkyl or have a substituent! /, May! /, C
  • R 2 may have a hydrogen atom or a substituent, or may have C alkyl or a substituent! /
  • R 3 to R 5 are each independently a hydrogen atom or a substituent
  • the antioxidant containing the phenolic compound represented by these The antioxidant containing the phenolic compound represented by these.
  • the antioxidant according to (5) or (6) comprising at least one selected from the group forces of guaiacol, bulguaiacol, eugenol, isoeugenol and 2,4,6 trimethylphenol.
  • step d calculating the difference between the amount of malondialdehyde measured in step a and the amount of malondialdehyde measured in step c;
  • FIG. 1 shows an embodiment of the evaluation method of the present invention.
  • FIG. 2 shows the amount of fading of
  • FIG. 3 shows the amount of fading of the / 3 straight mouth ten days after the addition of various substances.
  • FIG. 4 shows changes in malondialdehyde after 5 days when various substances are added.
  • the present invention relates to a method for preventing acidification, which comprises causing a phenolic compound to coexist with a target substance in a volatizable state.
  • the phenolic compound refers to a compound having a skeleton structure in which 1 to 3 hydroxyl groups are directly bonded to a benzene ring, and the benzene ring further having a substituent.
  • phenolic compounds do not include phenol itself! /.
  • the substituents are halogen, C alkyl, C alkyl, C alkyl, C alkoxy.
  • the number of substituents is preferably 1 to 3.
  • halogen is preferably selected from fluorine, chlorine, bromine or iodine.
  • 1-6 2-6 2-6 1-6 Coxy alone or as part of another group, includes alkyl, alkyl, alkyl, or alkoxy containing the specified number of carbon atoms, respectively. It may be linear or branched.
  • the phenolic compound of the present invention preferably has one hydroxyl group directly bonded to the benzene ring, and in this case, C alkoxy or C
  • a compound having volatility at room temperature that is, about 25 ° C. is used as the phenolic compound.
  • the phenolic compound is preferably of formula I:
  • R 1 may have a substituent, may be C alkyl or have a substituent! /, May! /, C
  • R 2 may have a hydrogen atom or a substituent, or may have C alkyl or a substituent! /
  • R 3 to R 5 are each independently a hydrogen atom or a substituent
  • the phenolic compound containing the compound of the formula I includes stereoisomers such as several isomers, rotational isomers and optical isomers of the above compounds, and salts and solvates.
  • the salt is not particularly limited, and examples thereof include ammonium salts such as trimethylammonium salt, alkali metal salts such as sodium and potassium salts, alkaline earth metal salts such as calcium and magnesium salts, and the like. Is mentioned.
  • Examples of the substituent in ⁇ ⁇ include, for example, halogen, C alkyl, C alk-
  • C alkyl and C alkoxy have a maximum of three substituents.
  • R 1 is preferably C alkyl or C alkoxy, more preferably C alkyl.
  • R 2 is preferably a hydrogen atom, C alkyl, C alkyl or C alkyl.
  • R 3 to R 5 are preferably each independently a hydrogen atom, halogen or C alkyl.
  • R 1 is C alkyl, preferably R 2 and R 3 are each independently C
  • R 4 and R 5 are hydrogen atoms.
  • R 1 is C alkoxy, preferably R 2 is C alkell and R 3 to R 5
  • phenolic compound in the present invention include 4-aryl 2,6-dimethoxyphenol, 4-arylphenol, force rubachlor, catechol, cresol, m-taresole, o-cresol, p-cresol, dihydro Eugenol, 2, 6 Dimethoki Siphenol, 2,3-Dimethylphenol, 2,6 Dimethylphenol, 3,5 Dimethylphenol, p-Ethoxyphenol, 4-Ethylda Ayacol, 2 Ethenophenol, 3 Ethylphenol, 4 Ethylphenol, 2 Ethylthioenol, Eugen Nonole, Guayako Nore, Vininole Guayako Nore, Hexenoresi Hexinorecetanol, 4-Hydroxybenzoitquaside, 4-Hydroxybenzylethyl ether, Isoeugenol, 2-Isopropylphenol, 4-Isopropylphenol, 3- Methoxy-1-5-methylphenol, 3-me
  • the phenolic compound may be used alone or in combination of two or more.
  • the present invention is characterized in that the phenolic compound as described above coexists with the target substance in a volatizable state.
  • the phenolic compound may be a synthetic compound or a natural one extracted from a plant.
  • guaiacol can extract forces such as sasa
  • eugenol can extract forces such as clove, keihi, -kuzuku, pimento
  • isoeugenol can extract forces such as kuzukuku.
  • a phenolic compound produced under the processing conditions of food and natural products For example, vinyl diaiacol produced during roasting of coffee can be mentioned.
  • To coexist with a target substance in a volatilizable state means to allow the phenolic compound to coexist with the target substance in a volatilized state, or to preserve the phenolic property for at least a certain period in the process of storage or the like. It means that the compound is volatilized and coexists with the target substance.
  • the method includes volatilizing the phenolic compound and bringing it into contact with the target substance, or bringing the phenolic compound in a gaseous state into contact with the target substance.
  • the concentration of the volatile phenolic compound in the space can be reduced.
  • the volatile phenolic compound can be efficiently brought into contact with the target substance.
  • the target substance and the phenolic compound are allowed to coexist in a suitable container.
  • the container is preferably a sealed container, but may not be a complete sealed container.
  • the target substance and the phenolic compound are placed in the same room, for example, the same storage room, a display shelf, Coexist in the case etc.
  • the anti-oxidation agent that is widely used at present is used by adding to the target substance, it is necessary to consider the solubility in the target object.
  • acidity and bitterness may be imparted and coloring may occur. Therefore, the method of the present invention in which the phenolic compound is allowed to coexist with the target substance in a volatilizable state can be a simpler method for preventing acidification than the conventional acid inhibitor that requires addition.
  • a phenolic compound is usually present in an amount of 20 to 80 ⁇ mol, preferably 40 to 60 ⁇ mol, per lg of the subject substance under the condition that the phenolic compound strength is 25 ° C.
  • the Ministry of Health, Labor and Welfare has indicated a provisional guideline value that the indoor volatile organic matter (VOC) concentration should be kept to 400 gZm 3 or less, so organic substances including phenolic compounds in volatiles It is desirable that the upper limit of the substance concentration is about 400 ⁇ gZm 3 .
  • the target substance for preventing acidification in the present invention is not particularly limited, and examples thereof include foods, pharmaceuticals, quasi drugs, cosmetics, and feeds.
  • the present invention is particularly preferably used for the prevention of acidification of an oily component or a substance containing an oily component.
  • the oily component is not particularly limited and may be synthetic or natural.
  • hydrocarbons straw steals, animal and vegetable oils and fats, waxes, goose fats, higher fatty acids, and higher alcohols , Silicone-based substances, sterols, greaves, etc., which have been treated enzymatically (hydrolysis, transesterification, etc.) or chemical treatment (transesterification, hydrogenation, etc.).
  • Examples of the substance containing an oily component include foods and drinks, pharmaceuticals, quasi drugs, cosmetics, and feeds containing an oily component.
  • ramen, tanmen, udon, buckwheat, macaroni, spaghetti, fried rice cake, non-fried rice cake, etc . powder and liquid soup
  • milk such as yogurt, prepared milk, infant formula, ice cream, yogurt, cream, whipped cream Products
  • Chikuwa power mackerel, fish sausages, fish ham and other marine products
  • Frozen foods such as fried chicken, frozen fried food, frozen dumplings, frozen sweet potatoes; miso, hamburger, ham, sausage, dumplings, sweet potatoes, bread, cooking oil, butter, margarine, shortening, cheese, mayonnaise, dressing, beverage, health Food, treatment Other foods such as food; lipstick, cosmetic cream, milky lotion, shi
  • the present invention also provides formula I:
  • R 1 may have a substituent, may be C alkyl or have a substituent! /, May! /, C
  • R 2 may have a hydrogen atom or a substituent, or may have C alkyl or a substituent! /
  • R 3 to R 5 are each independently a hydrogen atom or a substituent
  • the present invention relates to an antioxidant containing a phenolic compound represented by the formula:
  • the compounds of formula I and preferred compounds are the same as described for the antioxidant method.
  • the antioxidant of the present invention may contain one or more compounds as the compound of formula I.
  • the antioxidant of the present invention is preferably for preventing the oxidation of oily components.
  • the oil component is as described above.
  • the phenolic compound is volatilized.
  • the phenolic compound that has been vaporized into gas comes into contact with the target substance, and is in a state where it can exhibit the effect of preventing acidification.
  • the present invention also relates to a method for evaluating the antioxidant ability of a test substance in a volatile state.
  • the present invention relates to a method for evaluating the antioxidant ability of a test substance in a volatile state.
  • A) a step of measuring the absorbance of a solution containing linoleic acid and
  • the above embodiment utilizes the fact that ⁇ -carotene reacts with the reaction of acidified linoleic acid and ⁇ -carotene over time.
  • the volatilized test substance reacts with the ⁇ -carotene solution to suppress the fading of ⁇ -carotene.
  • the antioxidant ability of the test substance can be evaluated.
  • a surfactant is not particularly limited, but for example, Tween 40 can be used.
  • As the solvent water or ethanol can be used, and a buffer solution may be prepared if desired.
  • Concentration of Reno one Honoré acid in the solution is usually 100 to 500 8/1! 1, preferably 200 ⁇ 400 ⁇ gZmL, concentration of ⁇ - carotene, usually 5 to 50 GZmL, preferably 10 to 40 mu gZmL.
  • the pH of the solution is normally 5-8.
  • the time for placing the solution and the test substance in the sealed container is appropriately selected, but is usually 0.5 to 3 hours, preferably 1 to 2.5 hours, and the temperature is usually 10 to 30 ° C. .
  • the solution and the test substance may be introduced into another hole using, for example, a 96-well plate and placed in a sealed container. Disposing separately means that the solution and the test substance are not mixed or contacted.
  • the present invention relates to a method for evaluating the antioxidative ability of a test substance to an oily component in a volatile state, comprising: a) an oily component to which linoleic acid and
  • the above embodiment also reacts 13-carotene with linoleic acid that has been acidified over time, It uses the discoloration of carotene, and is different in that it uses an oily component with linoleic acid added.
  • the oily component is not particularly limited, but may be appropriately selected from the above oily components and the like which are preferably liquids at the temperature to be tested, usually room temperature.
  • corn oil, soybean oil, rapeseed oil, sesame oil, cottonseed oil, safflower oil, sunflower oil, peanut oil, rice germ oil, wheat germ oil, brown rice germ oil, pearl barley oil, mackerel damian nut oil, garlic oil, camellia oil Vegetable oils such as palm oil and olive oil can be used.
  • the concentration of linoleic acid in the oily component is usually 0.1 to 6 mgZmL, preferably 0.5 to 5 mgZmL.
  • gm is preferably 3 to 50 ⁇ g ZmL.
  • the present invention relates to a method for evaluating the antioxidative ability of an analyte in an volatile state of a test substance, comprising: a) measuring the amount of malondialdehyde in the oil component; b) A step of separately placing the oily component and the test substance in a sealed container; c) a step of measuring the amount of malondialdehyde in the oily component after a certain period of time; and d) the amount of malondialdehyde measured in step a) Calculating the difference in the amount of malondialdehyde measured in steps c and c,
  • Malondialdehyde is a secondary product of lipid peroxide and reacts with acid-conditioned thiobarbituric acid to form a red pigment.
  • Lipid peracid can be measured by measuring the absorption wavelength of the resulting red pigment at 595 nm (Ohkawa H et al, Anal. Biochem., 95, 351-358 (1979), Kikukawa K et al "Anal Biochem., 202: 249-255 (19 92)).
  • the time for placing the oily component and the test substance in the sealed container is an appropriately selected force.
  • L0 days preferably 5 to 7 days.
  • the temperature is usually 50-60 ° C.
  • the evaluation method using the oil component is advantageous in that it can more accurately evaluate the antioxidant ability of the test substance against the oil component.
  • the anti-acid ability is evaluated by measuring the fading of ⁇ -strength by the difference in absorbance, after 150 minutes at room temperature (25 ° C) in the presence of 500 mol of the test substance. If the difference in absorbance is 0.8 or less, preferably 0.7 or less, the test substance can be determined to have an antioxidant ability in a volatile state. Alternatively, if the difference in absorbance is 1.5 or less, preferably 1.2 or less after 5 days at 50 ° C in the presence of 500 mol of the test substance, the test substance is in a volatile state. It can be determined that it has antioxidant ability.
  • the anti-acidic ability is evaluated by measuring the amount of malondialdehyde, control of the amount of malondialdehyde after 5 days at 50 ° C in the presence of 500 ⁇ mol of the test substance. If the ratio is 0.8 or less per lg of oily component, preferably 0.6 or less, the test substance can be determined to have antioxidant ability in a volatile state.
  • the test substance is not particularly limited and may be liquid or solid.
  • peptides, proteins, non-peptidic compounds, synthetic compounds, fermented products, cell extracts, plant extracts, animal tissue extracts, etc. are used, and these substances may be novel substances. It may be a known substance.
  • the 96-well plate used was TPP TISSUE CULTURE TEST PLATES 96F.
  • an anero pack jar (inside dimensions: 19.5 cm ⁇ 19.7 cm ⁇ l. 8 cm) manufactured by Sgiamagen Co., Ltd. was used.
  • As a microplate reader Nippon Bio-Rad (Model550) was used. All reagents were purchased from Wako Pure Chemical.
  • j8-carotene was prepared at lmg / mL, linoleic acid at 0.1 lg / mL, and Tween 40 at 0.2 gZmL.
  • sodium dihydrogen phosphate was adjusted to a concentration of 24 g / mL (0.2 M)
  • disodium hydrogen phosphate was adjusted to a concentration of 28 g ZmL (0.2 M).
  • the phenolic compound of the present invention has an excellent antioxidant power in a volatile state.
  • the 96-well plate used was TPP TISSUE CULTURE TEST PLATES 96F.
  • an anero pack jar (inside dimensions: 19.5 cm ⁇ 19.7 cm ⁇ l. 8 cm) manufactured by Sgiamagen Co., Ltd. was used.
  • As a microplate reader Nippon Bio-Rad (Model550) was used. Reagents were purchased from Wako Pure Chemical.
  • the concentration of ⁇ -strength mouth is lmgZmL and linoleic acid is 0.lgZmL
  • the ⁇ -carotene solution (240 L) and linoleic acid solution (480 L) were placed in a test tube with a lid, and the black mouth form was completely removed with nitrogen gas. Then, tocopherol-removed corn oil (6m
  • the acetic acid buffer was prepared by dissolving 20 mL of acetic acid in water to make 10 mL, and adjusted to pH 3.5 with ION NaOH. The 8% TBA solution was heated and then subjected to ultrasound to completely dissolve the reagent.
  • FIG. 3 shows the amount of decrease in absorbance after 5 days when each substance is added, that is, the amount of fading of ⁇ -strength.
  • Fig. 4 shows the ratio of malondialdehyde to control after 5 days when each substance was added.
  • the phenolic compounds bull guaiacol, isoeugenol, eugenol, and guaiacol were volatilized in a sealed container, they showed strong antioxidant capacity.
  • the other substances used for comparison did not show any action, and it was found that this acid / anti-oxidation effect was peculiar to phenolic compounds.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Abstract

La présente invention concerne un procédé d'inhibition d'oxydation qui est excellent en termes de pouvoir antioxydant, est sans risque et assure une grande polyvalence. On propose un procédé d'inhibition d'oxydation, permettant à un composé phénolique sous forme volatile de coexister avec une substance objet.
PCT/JP2006/306264 2006-03-28 2006-03-28 Procede d'inhibition d'oxydation utilisant un composant volatil WO2007110924A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/JP2006/306264 WO2007110924A1 (fr) 2006-03-28 2006-03-28 Procede d'inhibition d'oxydation utilisant un composant volatil
JP2008507311A JPWO2007110924A1 (ja) 2006-03-28 2006-03-28 揮発性成分を用いた酸化防止方法

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PCT/JP2006/306264 WO2007110924A1 (fr) 2006-03-28 2006-03-28 Procede d'inhibition d'oxydation utilisant un composant volatil

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013103147A1 (fr) 2011-12-27 2013-07-11 Dow Corning Toray Co., Ltd. Silicone modifié par dérivé de diglycérol, émulsifiant pour une émulsion eau-dans-huile l'utilisant, préparation pour usage externe et composition cosmétique
JP2014509845A (ja) * 2011-02-07 2014-04-24 フイルメニツヒ ソシエテ アノニム 抗真菌性のフレーバリング成分およびフレーバリング組成物
JP2014143951A (ja) * 2013-01-29 2014-08-14 Kinki Univ サフラン色素の退色防止方法
US9169409B2 (en) 2008-11-07 2015-10-27 Lg Display Co., Ltd. Ink composition for imprint lithography and roll printing

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JP2004093061A (ja) * 2002-09-03 2004-03-25 Mitsubishi Electric Corp 冷蔵庫、抗酸化剤用収納容器
JP2004238453A (ja) * 2003-02-05 2004-08-26 Sanwa Shiyurui Kk 抗酸化作用を有する組成物及び該組成物の製造方法

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JPH03506024A (ja) * 1988-07-22 1991-12-26 シロス・タッチ・エルティーディー 皮膚病の治療及び創傷の治癒を促進させる組成物及び方法
JP2000087268A (ja) * 1998-07-29 2000-03-28 Excor Korrosionsforschung Gmbh 気相腐蝕抑制剤及びその製造方法
JP2001226211A (ja) * 2000-02-09 2001-08-21 Sannin:Kk ハナミョウガ属植物含有難揮発性成分より成る防虫剤および酸化防止剤
JP2001231536A (ja) * 2000-02-18 2001-08-28 Takara Shuzo Co Ltd 新規みりん類及びその製造方法
JP2003055314A (ja) * 2001-08-20 2003-02-26 Fujita Masao ヒドロキシけい皮酸誘導体及びこれを用いた抗酸化剤
JP2004093061A (ja) * 2002-09-03 2004-03-25 Mitsubishi Electric Corp 冷蔵庫、抗酸化剤用収納容器
JP2004238453A (ja) * 2003-02-05 2004-08-26 Sanwa Shiyurui Kk 抗酸化作用を有する組成物及び該組成物の製造方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9169409B2 (en) 2008-11-07 2015-10-27 Lg Display Co., Ltd. Ink composition for imprint lithography and roll printing
JP2014509845A (ja) * 2011-02-07 2014-04-24 フイルメニツヒ ソシエテ アノニム 抗真菌性のフレーバリング成分およびフレーバリング組成物
WO2013103147A1 (fr) 2011-12-27 2013-07-11 Dow Corning Toray Co., Ltd. Silicone modifié par dérivé de diglycérol, émulsifiant pour une émulsion eau-dans-huile l'utilisant, préparation pour usage externe et composition cosmétique
JP2014143951A (ja) * 2013-01-29 2014-08-14 Kinki Univ サフラン色素の退色防止方法

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