TW201840299A - 玻尿酸複合奈米粒子 - Google Patents
玻尿酸複合奈米粒子 Download PDFInfo
- Publication number
- TW201840299A TW201840299A TW107111567A TW107111567A TW201840299A TW 201840299 A TW201840299 A TW 201840299A TW 107111567 A TW107111567 A TW 107111567A TW 107111567 A TW107111567 A TW 107111567A TW 201840299 A TW201840299 A TW 201840299A
- Authority
- TW
- Taiwan
- Prior art keywords
- hyaluronic acid
- composite nanoparticle
- zwitterionic
- present
- polymer
- Prior art date
Links
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 74
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 73
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 73
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 71
- 239000002131 composite material Substances 0.000 title claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000002245 particle Substances 0.000 claims abstract description 27
- 229920000642 polymer Polymers 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 229950004354 phosphorylcholine Drugs 0.000 claims description 3
- 239000011859 microparticle Substances 0.000 abstract description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 19
- 210000003491 skin Anatomy 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 229960003237 betaine Drugs 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- 229920001661 Chitosan Polymers 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- -1 sodium hyaluronic acid salt Chemical class 0.000 description 7
- 150000001449 anionic compounds Chemical class 0.000 description 6
- 229920006318 anionic polymer Polymers 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000010419 fine particle Substances 0.000 description 6
- 230000003020 moisturizing effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 229920006317 cationic polymer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HZNDZTXHJZSPRN-UHFFFAOYSA-N CC(C)=COCCOP([O-])(OCC[N+](C)(C)C)=O Chemical compound CC(C)=COCCOP([O-])(OCC[N+](C)(C)C)=O HZNDZTXHJZSPRN-UHFFFAOYSA-N 0.000 description 3
- 229920006322 acrylamide copolymer Polymers 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
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- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 3
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
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- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
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- DLRVVLDZNNYCBX-UHFFFAOYSA-N Polydextrose Polymers OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(O)O1 DLRVVLDZNNYCBX-UHFFFAOYSA-N 0.000 description 2
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- IHSPMDXQWYKHOA-UHFFFAOYSA-N dodecyl 2-(dimethylamino)acetate Chemical compound CCCCCCCCCCCCOC(=O)CN(C)C IHSPMDXQWYKHOA-UHFFFAOYSA-N 0.000 description 2
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- 238000010030 laminating Methods 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
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- 229960005323 phenoxyethanol Drugs 0.000 description 2
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- 238000003860 storage Methods 0.000 description 2
- 238000005199 ultracentrifugation Methods 0.000 description 2
- NCBISIFFSNXYQJ-UHFFFAOYSA-N 1-dodecyl-4,5-dihydroimidazole Chemical compound CCCCCCCCCCCCN1CCN=C1 NCBISIFFSNXYQJ-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- FIEMNCUPUKWJBC-UHFFFAOYSA-N 2-methylprop-1-ene-1-thiol Chemical compound CC(C)=CS FIEMNCUPUKWJBC-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- HGWMEBOCADNMGF-AWGDKMGJSA-N C(C)N[C@H]1C(O)(O[C@@H]([C@H]([C@@H]1O)O)CO)C1=CC=CC=2C3=CC=CC=C3CC12 Chemical group C(C)N[C@H]1C(O)(O[C@@H]([C@H]([C@@H]1O)O)CO)C1=CC=CC=2C3=CC=CC=C3CC12 HGWMEBOCADNMGF-AWGDKMGJSA-N 0.000 description 1
- FRVJGSHGYZCQIY-UHFFFAOYSA-N CCC(C[N+](C)(C)C)OP([O-])(OCC)=O Chemical compound CCC(C[N+](C)(C)C)OP([O-])(OCC)=O FRVJGSHGYZCQIY-UHFFFAOYSA-N 0.000 description 1
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- 229920001287 Chondroitin sulfate Polymers 0.000 description 1
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- 229920000288 Keratan sulfate Polymers 0.000 description 1
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- 235000019482 Palm oil Nutrition 0.000 description 1
- 229920000805 Polyaspartic acid Polymers 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
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- 229920002385 Sodium hyaluronate Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
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- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
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- 238000005054 agglomeration Methods 0.000 description 1
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- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical group O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
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- 238000005576 amination reaction Methods 0.000 description 1
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
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- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
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- 230000008859 change Effects 0.000 description 1
- 229940045110 chitosan Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
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- PSHRANCNVXNITH-UHFFFAOYSA-N dimethylamino acetate Chemical compound CN(C)OC(C)=O PSHRANCNVXNITH-UHFFFAOYSA-N 0.000 description 1
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
- KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
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- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Birds (AREA)
- Molecular Biology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017-068605 | 2017-03-30 | ||
| JP2017068605 | 2017-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201840299A true TW201840299A (zh) | 2018-11-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW107111567A TW201840299A (zh) | 2017-03-30 | 2018-03-30 | 玻尿酸複合奈米粒子 |
Country Status (2)
| Country | Link |
|---|---|
| TW (1) | TW201840299A (ja) |
| WO (1) | WO2018182003A1 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4018998A4 (en) * | 2019-08-21 | 2023-09-27 | Shiseido Company, Ltd. | COSMETIC PRODUCT |
| TW202245732A (zh) | 2021-02-10 | 2022-12-01 | 日商資生堂股份有限公司 | 化妝料 |
| CN113952506B (zh) * | 2021-09-26 | 2023-03-21 | 华南理工大学 | 一种仿生软骨表层修复水凝胶的制备方法 |
| CN120152695A (zh) | 2022-12-01 | 2025-06-13 | 株式会社资生堂 | 组合物 |
| WO2025173703A1 (ja) * | 2024-02-13 | 2025-08-21 | ワミレスコスメティックス株式会社 | 化粧料 |
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| JP2003073251A (ja) * | 2001-08-31 | 2003-03-12 | Shiseido Co Ltd | 皮膚外用剤 |
| JP5412078B2 (ja) * | 2008-10-06 | 2014-02-12 | ドクタープログラム株式会社 | 皮膚外用剤 |
| JP2010150151A (ja) * | 2008-12-24 | 2010-07-08 | Hosokawa Micron Corp | ヒアルロン酸担持ナノ粒子及びヒアルロン酸含有複合粒子並びにそれらを用いた化粧料 |
| JP2013159605A (ja) * | 2012-02-09 | 2013-08-19 | Shiseido Co Ltd | 皮膚外用剤組成物 |
| US10357437B2 (en) * | 2015-03-13 | 2019-07-23 | Nof Corporation | Composition for nanoemulsion emulsification, bicontinuous microemulsion, cosmetic, and method for producing same |
-
2018
- 2018-03-30 TW TW107111567A patent/TW201840299A/zh unknown
- 2018-03-30 WO PCT/JP2018/013947 patent/WO2018182003A1/ja not_active Ceased
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| Publication number | Publication date |
|---|---|
| WO2018182003A1 (ja) | 2018-10-04 |
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