JP3557044B2 - 皮膚柔軟化剤 - Google Patents
皮膚柔軟化剤 Download PDFInfo
- Publication number
- JP3557044B2 JP3557044B2 JP13940596A JP13940596A JP3557044B2 JP 3557044 B2 JP3557044 B2 JP 3557044B2 JP 13940596 A JP13940596 A JP 13940596A JP 13940596 A JP13940596 A JP 13940596A JP 3557044 B2 JP3557044 B2 JP 3557044B2
- Authority
- JP
- Japan
- Prior art keywords
- hyaluronic acid
- acetylated
- acetyl group
- test
- molecular weight
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 239000003974 emollient agent Substances 0.000 title claims description 8
- 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 claims description 71
- 229920002674 hyaluronan Polymers 0.000 claims description 70
- 229960003160 hyaluronic acid Drugs 0.000 claims description 70
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 40
- 238000006467 substitution reaction Methods 0.000 claims description 36
- 125000003047 N-acetyl group Chemical group 0.000 claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 230000000694 effects Effects 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 238000012360 testing method Methods 0.000 description 28
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 26
- 229920002385 Sodium hyaluronate Polymers 0.000 description 24
- 229940010747 sodium hyaluronate Drugs 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 23
- 210000003491 skin Anatomy 0.000 description 19
- 239000012085 test solution Substances 0.000 description 18
- 238000006640 acetylation reaction Methods 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 230000003020 moisturizing effect Effects 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 230000021736 acetylation Effects 0.000 description 10
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 9
- 239000001540 sodium lactate Substances 0.000 description 9
- 235000011088 sodium lactate Nutrition 0.000 description 9
- 229940005581 sodium lactate Drugs 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000010586 diagram Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 108010076876 Keratins Proteins 0.000 description 6
- 102000011782 Keratins Human genes 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- 210000000434 stratum corneum Anatomy 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000007809 chemical reaction catalyst Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003906 humectant Substances 0.000 description 3
- 229940014041 hyaluronate Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- -1 acetyl Hyaluronic acid Chemical compound 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical class CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000016942 Elastin Human genes 0.000 description 1
- 108010014258 Elastin Proteins 0.000 description 1
- 108010022355 Fibroins Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 108010003272 Hyaluronate lyase Proteins 0.000 description 1
- 102000001974 Hyaluronidases Human genes 0.000 description 1
- 239000004166 Lanolin Chemical class 0.000 description 1
- 239000008156 Ringer's lactate solution Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229920002549 elastin Polymers 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002948 pantothenic acids Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229960002816 potassium chloride Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 229940045920 sodium pyrrolidone carboxylate Drugs 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- HYRLWUFWDYFEES-UHFFFAOYSA-M sodium;2-oxopyrrolidine-1-carboxylate Chemical compound [Na+].[O-]C(=O)N1CCCC1=O HYRLWUFWDYFEES-UHFFFAOYSA-M 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 235000019263 trisodium citrate Nutrition 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13940596A JP3557044B2 (ja) | 1995-06-29 | 1996-05-08 | 皮膚柔軟化剤 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7-186156 | 1995-06-29 | ||
| JP18615695 | 1995-06-29 | ||
| JP13940596A JP3557044B2 (ja) | 1995-06-29 | 1996-05-08 | 皮膚柔軟化剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH0971602A JPH0971602A (ja) | 1997-03-18 |
| JP3557044B2 true JP3557044B2 (ja) | 2004-08-25 |
| JPH0971602A5 JPH0971602A5 (enExample) | 2004-12-16 |
Family
ID=26472227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13940596A Expired - Lifetime JP3557044B2 (ja) | 1995-06-29 | 1996-05-08 | 皮膚柔軟化剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3557044B2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010196048A (ja) * | 2009-01-30 | 2010-09-09 | Kose Corp | 新規な水溶性ポリマー及びそれを含有する化粧料又は皮膚外用剤 |
| JP2010254974A (ja) * | 2009-03-31 | 2010-11-11 | Kose Corp | 水溶性コポリマー及びそれを配合する化粧料又は皮膚外用剤 |
| KR20140127796A (ko) * | 2012-02-10 | 2014-11-04 | 가부시키가이샤 시세이도 | 수중유형 유화 피부 화장료 |
| JP2016196430A (ja) * | 2015-04-03 | 2016-11-24 | 株式会社ダイセル | エクオール及び保湿剤を含有する外用組成物 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3634113B2 (ja) * | 1997-03-31 | 2005-03-30 | 株式会社資生堂 | 皮膚外用剤 |
| JPH10279418A (ja) * | 1997-03-31 | 1998-10-20 | Shiseido Co Ltd | 皮膚外用剤 |
| JP2004262777A (ja) | 2003-02-27 | 2004-09-24 | Shiseido Co Ltd | アセチル化ヒアルロン酸含有眼用医薬組成物 |
| JP2006349372A (ja) * | 2005-06-13 | 2006-12-28 | Shiseido Co Ltd | 角層中の酸化タンパク質を指標とする肌の柔軟性・弾力性を評価する方法 |
| JP4993890B2 (ja) * | 2005-09-15 | 2012-08-08 | ロート製薬株式会社 | 皮膚外用剤 |
| JP2007186688A (ja) * | 2005-12-13 | 2007-07-26 | Shiseido Co Ltd | 低分子量ヒアルロン酸の製造方法 |
| JP2007186689A (ja) * | 2005-12-13 | 2007-07-26 | Shiseido Co Ltd | 低分子量ヒアルロン酸の製造方法 |
| JP2008050311A (ja) * | 2006-08-25 | 2008-03-06 | Kowa Co | 使用感の良い乳化組成物 |
| US20100008878A1 (en) * | 2007-08-09 | 2010-01-14 | Foodchemifa Co., Ltd | Propylene glycol hyaluronate, and skincare preparation for external use comprising same |
| JP2010208950A (ja) * | 2009-03-06 | 2010-09-24 | Nippon Zettoc Co Ltd | 化粧料およびその製造方法 |
| CN113288824A (zh) | 2013-10-09 | 2021-08-24 | 株式会社资生堂 | 低拉丝性增稠剂和混合有该增稠剂的化妆品 |
| GB201703850D0 (en) * | 2017-03-10 | 2017-04-26 | Givaudan Sa | Improvements in or relating to organic compounds |
-
1996
- 1996-05-08 JP JP13940596A patent/JP3557044B2/ja not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010196048A (ja) * | 2009-01-30 | 2010-09-09 | Kose Corp | 新規な水溶性ポリマー及びそれを含有する化粧料又は皮膚外用剤 |
| JP2010254974A (ja) * | 2009-03-31 | 2010-11-11 | Kose Corp | 水溶性コポリマー及びそれを配合する化粧料又は皮膚外用剤 |
| KR20140127796A (ko) * | 2012-02-10 | 2014-11-04 | 가부시키가이샤 시세이도 | 수중유형 유화 피부 화장료 |
| JP2016196430A (ja) * | 2015-04-03 | 2016-11-24 | 株式会社ダイセル | エクオール及び保湿剤を含有する外用組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0971602A (ja) | 1997-03-18 |
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