JP6099577B2 - ポリグリセリンジアルキル又はアルケニルエーテル、及びこれを含有する化粧料用組成物 - Google Patents
ポリグリセリンジアルキル又はアルケニルエーテル、及びこれを含有する化粧料用組成物 Download PDFInfo
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- JP6099577B2 JP6099577B2 JP2013557504A JP2013557504A JP6099577B2 JP 6099577 B2 JP6099577 B2 JP 6099577B2 JP 2013557504 A JP2013557504 A JP 2013557504A JP 2013557504 A JP2013557504 A JP 2013557504A JP 6099577 B2 JP6099577 B2 JP 6099577B2
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- JP
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- Prior art keywords
- ether
- dialkyl
- alkenyl
- cosmetic composition
- acid
- 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 - Fee Related
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- -1 alkenyl ether Chemical compound 0.000 title claims description 202
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 102
- 239000002537 cosmetic Substances 0.000 title claims description 62
- 239000000203 mixture Substances 0.000 title claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229920000223 polyglycerol Polymers 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 description 50
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 22
- 239000004094 surface-active agent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 18
- HANWHVWXFQSQGJ-UHFFFAOYSA-N 1-tetradecoxytetradecane Chemical compound CCCCCCCCCCCCCCOCCCCCCCCCCCCCC HANWHVWXFQSQGJ-UHFFFAOYSA-N 0.000 description 17
- LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 description 15
- 229940028820 didecyl ether Drugs 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 238000005187 foaming Methods 0.000 description 13
- CMYGERBJJJPWHH-UHFFFAOYSA-N heptacosane-13,14,15-triol Chemical compound CCCCCCCCCCCCC(O)C(O)C(O)CCCCCCCCCCCC CMYGERBJJJPWHH-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 10
- 239000003599 detergent Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
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- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- 229940085632 distearyl ether Drugs 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
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- 239000003054 catalyst Substances 0.000 description 7
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- LKPJRFVEJFVTFQ-UHFFFAOYSA-N hentriacontane-15,16,17-triol Chemical compound CCCCCCCCCCCCCCC(O)C(O)C(O)CCCCCCCCCCCCCC LKPJRFVEJFVTFQ-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
- HZKOKZZUBXUMSE-CLFAGFIQSA-N (9Z,30Z)-nonatriaconta-9,30-diene-19,20,21-triol Chemical compound C(CCCCCCC\C=C/CCCCCCCC)C(C(C(O)CCCCCCCC\C=C/CCCCCCCC)O)O HZKOKZZUBXUMSE-CLFAGFIQSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 229910018287 SbF 5 Inorganic materials 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
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- 238000011156 evaluation Methods 0.000 description 4
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- 125000001165 hydrophobic group Chemical group 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 229920005615 natural polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 210000000245 forearm Anatomy 0.000 description 3
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- 231100000475 skin irritation Toxicity 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
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- NVKSMKFBUGBIGE-UHFFFAOYSA-N 2-(tetradecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCOCC1CO1 NVKSMKFBUGBIGE-UHFFFAOYSA-N 0.000 description 2
- DDHJMUWKDMGQFH-KTKRTIGZSA-N 2-[[(z)-octadec-9-enoxy]methyl]oxirane Chemical compound CCCCCCCC\C=C/CCCCCCCCOCC1CO1 DDHJMUWKDMGQFH-KTKRTIGZSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 229910052627 muscovite Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 229960003921 octisalate Drugs 0.000 description 1
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 229910052628 phlogopite Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
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- CCTFOFUMSKSGRK-UHFFFAOYSA-N propan-2-olate;tin(4+) Chemical compound [Sn+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] CCTFOFUMSKSGRK-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
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- 229940092258 rosemary extract Drugs 0.000 description 1
- 235000020748 rosemary extract Nutrition 0.000 description 1
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
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- 230000001953 sensory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
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- QSQXISIULMTHLV-UHFFFAOYSA-N strontium;dioxido(oxo)silane Chemical compound [Sr+2].[O-][Si]([O-])=O QSQXISIULMTHLV-UHFFFAOYSA-N 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
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Description
本発明の他の目的は、前記ポリグリセリンジアルキル又はアルケニルエーテルを含有する化粧料用組成物を提供する。
本発明の他の目的は、洗浄力及び使用性を兼ね備えるクレンジング化粧料用組成物、すなわち、皮膚が濡れた状態でも、また濡れていない状態でもメイクアップ汚れに容易に馴染み、優れた洗浄力を発揮することができ、且つ、水ですすぐことによりすっきりと油性感を残すことなく洗い流すことができるクレンジング化粧料用組成物を提供することにある。
本発明の更に他の目的は、前記クレンジング化粧料用組成物を含有するクレンジング化粧料を提供することにある。
で表されるポリグリセリンジアルキル又はアルケニルエーテルを提供する。
本発明のポリグリセリンジアルキル又はアルケニルエーテルは、下記式(1)で表される。式中、R1、R2は、同一又は異なって、ヒドロキシル基を有していてもよい直鎖状若しくは分岐鎖状のアルキル基、又は直鎖状若しくは分岐鎖状のアルケニル基である。nはグリセリン単位の数を示し、2以上の整数である。
−CH2−CHOH−CH2O− (2)
−CH(CH2OH)CH2O− (3)
HLB値=(無機性値÷有機性値)×10
式(1)で表されるポリグリセリンジアルキル又はアルケニルエーテルは、例えば、触媒の存在下、脂肪族アルコールにアルキル又はアルケニルグリシジルエーテルを反応させてグリセリンジアルキル又はアルケニルエーテルを得、得られたグリセリンジアルキル又はアルケニルエーテルにグリシドールを反応させる方法により製造することができる。
工程(1):下記式(4)で表されるアルコールに下記式(5)で表されるグリシジルエーテルを反応させることにより下記式(6)で表される2級ヒドロキシル基を有するグリセリンジアルキル又はアルケニルエーテルを得る
工程(2):工程(1)で得られた下記式(6)で表される2級ヒドロキシル基を有するグリセリンジアルキル又はアルケニルエーテル1当量に対し、グリシドールをn当量反応させる
本発明のクレンジング化粧料用組成物は、上記ポリグリセリンジアルキル又はアルケニルエーテルと水を含有する。
本発明のクレンジング化粧料は、上記クレンジング化粧料用組成物を含有することを特徴とする。本発明のクレンジング化粧料は、ローション状、溶液状、乳液状、クリーム状、ジェル状等のいずれのタイプであっても良い。
下記デシルグリシジルエーテル1当量に対して8当量となる量のデシルアルコール(和光純薬工業(株)製試薬、886g)を仕込んだ後、窒素雰囲気下、1mol%塩化スズ(IV)(1.82g)を添加し、反応温度を80℃に維持しつつ、デシルグリシジルエーテル(四日市合成(株)製、150g)を1時間かけて滴下した。滴下終了後、1時間の熟成を行い、反応を停止するため水を加えた。
得られた反応粗液に、炭酸カリウム(和光純薬工業(株)製、9.67g)を加え、水分を除去した後に、ヘプタン(和光純薬工業(株)製、259g)にて希釈した。
ブフナー漏斗を使用して吸引ろ過し、少量のヘプタンで反応器のリンスを行い、ろ液を得た。
ろ液中のヘプタンをエバポレーターで留去後、150℃、減圧度2mmHgの減圧留去をすることにより未反応のデシルグリシジルエーテル留去し、ジデシルグリセロール372gを得た。
デシルグリシジルエーテルに代えてラウリルグリシジルエーテルを使用し、デシルアルコールに代えてラウリルアルコールを使用した以外は製造例1と同様にして、ジラウリルグリセロールを得た。
デシルグリシジルエーテルに代えてテトラデシルグリシジルエーテルを使用し、デシルアルコールに代えてテトラデシルアルコールを使用した以外は製造例1と同様にして、ジテトラデシルグリセロールを得た。
デシルグリシジルエーテルに代えてオレイルグリシジルエーテルを使用し、デシルアルコールに代えてオレイルアルコールを使用した以外は製造例1と同様にして、ジオレイルグリセロールを得た。
製造例2で得られたジラウリルグリセロール104gに対し、200℃、2mmHgでラウリルグリシジルエーテルを留去した後、28%ナトリウムメトキシドメタノール溶液(46.9g)を加え、100℃、2mmHg、10時間、減圧留去することによりメタノールを留去した。
その後、上記ジラウリルグリセロール1当量に対して2当量となる量のグリシドール(54.0g)を、70℃を維持しつつ、10時間かけて滴下し、1時間の熟成を経て、85%リン酸水溶液18.7gを加えて反応を停止した。
得られた反応粗液にメタノール150gを加え希釈した。
その後、加圧ろ過にて粗液中のリン酸塩を除去した後、150℃、常圧にてメタノールを留去し、さらに2mmHgで他の低沸成分を留去することによりトリグリセリンジラウリルエーテル(HLB:6.33)158gを得た。
製造例2で得られたジラウリルグリセロールに代えて、製造例3で得られたジテトラデシルグリセロールを使用した以外は実施例1と同様にして、トリグリセリンジテトラデシルエーテル(HLB:5.14)を得た。
グリシドールの使用量を2当量から3当量に変更した以外は実施例1と同様にして、テトラグリセリンジラウリルエーテル(HLB:6.94)を得た。得られた化合物の1H−NMR(400MHz、CDCl3)スペクトルデータを図1に示す。
製造例2で得られたジラウリルグリセロールに代えて、製造例1で得られたジデシルグリセロールを使用し、グリシドールの使用量を2当量から3当量に変更した以外は実施例1と同様にして、テトラグリセリンジデシルエーテル(HLB:6.87)を得た。得られた化合物の1H−NMR(400MHz、CDCl3)スペクトルデータを図2に示す。
製造例2で得られたジラウリルグリセロールに代えて、製造例4で得られたジオレイルグリセロールを使用し、グリシドールの使用量を2当量から3当量に変更した以外は実施例1と同様にして、テトラグリセリンジオレイルエーテル(HLB:5.25)を得た。
製造例2で得られたジラウリルグリセロールに代えて、製造例1で得られたジデシルグリセロールを使用し、グリシドールの使用量を2当量から4当量に変更した以外は実施例1と同様にして、ペンタグリセリンジデシルエーテル(HLB:8.86)を得た。得られた化合物の1H−NMR(400MHz、DMSO)スペクトルデータを図3に示す。
グリシドールの使用量を2当量から4当量に変更した以外は実施例1と同様にして、ペンタグリセリンジラウリルエーテル(HLB:10.0)を得た。得られた化合物の1H−NMR(400MHz、DMSO)スペクトルデータを図4に示す。
製造例2で得られたジラウリルグリセロールに代えて、製造例1で得られたジデシルグリセロールを使用し、グリシドールの使用量を2当量から6当量に変更した以外は実施例1と同様にして、ヘプタグリセリンジデシルエーテル(HLB:10.5)を得た。
グリシドールの使用量を2当量から6当量に変更した以外は実施例1と同様にして、ヘプタグリセリンジラウリルエーテル(HLB:11.3)を得た。
製造例2で得られたジラウリルグリセロールに代えて、製造例3で得られたジテトラデシルグリセロールを使用し、グリシドールの使用量を2当量から6当量に変更した以外は実施例1と同様にして、ヘプタグリセリンジテトラデシルエーテル(HLB:8.78)を得た。
グリシドールの使用量を2当量から8当量に変更した以外は実施例1と同様にして、ノナグリセリンジラウリルエーテル(HLB:12.3)を得た。
製造例2で得られたジラウリルグリセロールに代えて、製造例3で得られたジテトラデシルグリセロールを使用し、グリシドールの使用量を2当量から9当量に変更した以外は実施例1と同様にして、デカグリセリンジテトラデシルエーテル(HLB:12.2)を得た。
グリシドールの使用量を2当量から10当量に変更した以外は実施例1と同様にして、ウンデカグリセリンジラウリルエーテル(HLB:13.2)を得た。
製造例2で得られたジラウリルグリセロールに代えて、製造例3で得られたジテトラデシルグリセロールを使用し、グリシドールの使用量を2当量から10当量に変更した以外は実施例1と同様にして、ウンデカグリセリンジテトラデシルエーテル(HLB:11.0)を得た。
製造例2で得られたジラウリルグリセロールに代えて、製造例4で得られたジオレイルグリセロールを使用し、グリシドールの使用量を2当量から10当量に変更した以外は実施例1と同様にして、ウンデカグリセリンジオレイルエーテル(HLB:9.74)を得た
グリシドールの使用量を2当量から20当量に変更した以外は実施例1と同様にして、ヘンイコサグリセリンジラウリルエーテル(HLB:14.6)を得た。
下記表1に示される割合(重量%)で原料を配合して洗浄剤組成物を調製した。尚、界面活性剤は実施例で得られたものを使用した。
得られた洗浄剤組成物について、下記試験方法により、洗浄力、及び起泡力を評価した。
洗浄剤組成物の0.2%水溶液700mL(液温:30℃)に、人工汚巧を付着させた平面20cm2のガラス板を専用台にセットして沈め、撹拌羽を回転数250rpmで3分間回転させて洗浄した。
回転終了後、ガラス板を取り出し、乾燥させた後に重量を測定し、下記式を用いて洗浄率を算出し、下記基準で洗浄力を評価した。
洗浄率={(洗浄前の重量−洗浄後の重量)/洗浄前の重量}×100%
評価基準
◎:洗浄力95%以上
○:洗浄力85%以上、95%未満
△:洗浄力50%以上、85%未満
×:洗浄力50%未満
洗浄剤組成物の20倍希釈水溶液を調製し、この溶液100mL(液温:30℃)を500mLメスシリンダーに注入した。次いで、撹拌羽根を上記溶液中に設置し、1000rpmの回転数で1分間撹拌した。その後、生じた泡の体積(mL)を測定し泡立ち量と
した。前記泡立ち量から、下記基準により起泡力を評価した。
評価基準
◎:泡立ち300mL以上
○:泡立ち250mL以上、300mL未満
△:泡立ち200mL以上、250mL未満
×:泡立ち200mL未満
下記表2、3に示される割合(重量%)で原料を配合し、60℃にて撹拌して、クレンジング化粧料を得た。尚、界面活性剤は実施例で得られたものを使用した。
得られたクレンジング化粧料について、下記の方法により評価した。
1.乾いた状態での洗浄力試験
口紅(商品名「マキアージュ スーペリアルージュ RD759」、資生堂(株)製)0.2gを前腕に塗布し、実施例及び比較例で得られたクレンジング化粧料約0.5gを手に取り、10回マッサージして、口紅と馴染ませた。その後、水で洗い流し、口紅の落ち具合を目視で観察し、下記基準に従って評価した。また、洗浄後の皮膚感触を下記基準に従って官能評価した。
2.水に濡れた状態での洗浄力試験
口紅(商品名「マキアージュ スーペリアルージュ RD759」、資生堂(株)製)0.2gを前腕に塗布し、前腕を水で濡らした後、実施例及び比較例で得られたクレンジング化粧料約0.5gを手に取り、10回マッサージして、口紅と馴染ませた。その後、水で洗い流し、口紅の落ち具合を目視で観察し、下記基準に従って評価した。
洗浄力評価基準:
◎:完全に落ちた
○:ほぼ落ちた
△:少し残った
×:ほとんど落ちなかった
使用感評価基準:
◎:非常にさっぱりしている
○:さっぱりしている
△:ややヌルつきがある
×:ヌルつきがある
Claims (5)
- 請求項1に記載のポリグリセリンジアルキル又はアルケニルエーテルを含有する化粧料用組成物。
- 請求項1に記載のポリグリセリンジアルキル又はアルケニルエーテルを1〜70重量%、水を30〜99重量%含有するクレンジング化粧料用組成物。
- 請求項3に記載のクレンジング化粧料用組成物を含有するクレンジング化粧料。
- 更に、高分子化合物を含有する請求項4に記載のクレンジング化粧料。
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JP2012070869 | 2012-03-27 | ||
JP2012070869 | 2012-03-27 | ||
PCT/JP2013/052461 WO2013118676A1 (ja) | 2012-02-08 | 2013-02-04 | ポリグリセリンジアルキル又はアルケニルエーテル、及びこれを含有する化粧料用組成物 |
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US (1) | US20160009619A1 (ja) |
EP (1) | EP2813483A1 (ja) |
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JP2013194209A (ja) * | 2012-03-22 | 2013-09-30 | Daicel Corp | 洗浄剤組成物 |
KR20210004990A (ko) * | 2018-04-19 | 2021-01-13 | 주식회사 쿠라레 | 불포화 이중 결합 함유 화합물, 그것을 사용한 산소 흡수제, 및 수지 조성물 |
WO2020196199A1 (ja) * | 2019-03-22 | 2020-10-01 | 株式会社ダイセル | 半導体ウエハ表面の親水化処理液 |
JP7496305B2 (ja) | 2020-12-28 | 2024-06-06 | 株式会社ヤクルト本社 | クレンジング化粧料の評価方法 |
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JPS5444039A (en) * | 1977-09-12 | 1979-04-07 | Nippon Saafuakutanto Kougiyou | Cosmetics |
FR2467838A1 (fr) * | 1979-10-16 | 1981-04-30 | Oreal | Nouveaux composes non-ioniques polyoxyethylenes a deux chaines lipophiles, leur procede de preparation et compositions les contenant |
JPS5993022A (ja) * | 1982-11-16 | 1984-05-29 | Kao Corp | ポリオ−ルエ−テル化合物およびその製造法ならびにこれを含有する化粧料 |
JPH0672221B2 (ja) | 1982-12-08 | 1994-09-14 | 花王株式会社 | 発色組成物 |
JPS60224638A (ja) * | 1984-04-23 | 1985-11-09 | Kao Corp | 経皮吸収促進剤およびこれを含有する外用剤 |
JPS649304A (en) | 1987-07-01 | 1989-01-12 | Fujitsu Ltd | Height measuring apparatus |
JP3392980B2 (ja) | 1995-04-10 | 2003-03-31 | 花王株式会社 | 水系ジェル状洗浄剤組成物 |
JP3691678B2 (ja) * | 1999-02-18 | 2005-09-07 | 太陽化学株式会社 | 新規ポリエーテルポリオール化合物 |
US6683222B2 (en) * | 1999-02-18 | 2004-01-27 | Taiyo Kagaku Co., Ltd. | Polyether-polyol compound |
JP2001354998A (ja) | 2000-06-15 | 2001-12-25 | Lion Corp | 洗浄剤組成物 |
JP4157123B2 (ja) * | 2005-08-29 | 2008-09-24 | 第一工業製薬株式会社 | 乳化重合用乳化剤、ポリマーエマルションの製造方法及びポリマーエマルション |
JP2007269730A (ja) * | 2006-03-31 | 2007-10-18 | Kao Corp | (ポリ)グリセリルエーテルの製造方法 |
EP2152653A1 (en) * | 2007-04-27 | 2010-02-17 | Dow Global Technologies Inc. | Novel alkoxylate-containing compositions |
JP5444039B2 (ja) * | 2009-06-01 | 2014-03-19 | 三井化学東セロ株式会社 | 樹脂組成物、太陽電池封止材及びそれを用いた太陽電池モジュール |
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