CN114288205A - Hyaluronic acid multiple emulsion with stability improving effect, preparation method and application thereof - Google Patents
Hyaluronic acid multiple emulsion with stability improving effect, preparation method and application thereof Download PDFInfo
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- CN114288205A CN114288205A CN202111631995.8A CN202111631995A CN114288205A CN 114288205 A CN114288205 A CN 114288205A CN 202111631995 A CN202111631995 A CN 202111631995A CN 114288205 A CN114288205 A CN 114288205A
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- hyaluronic acid
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- 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 169
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 169
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 169
- 239000000839 emulsion Substances 0.000 title claims abstract description 115
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 230000000694 effects Effects 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 239000004480 active ingredient Substances 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 96
- 239000003995 emulsifying agent Substances 0.000 claims description 34
- 239000003921 oil Substances 0.000 claims description 23
- 235000019198 oils Nutrition 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 12
- -1 alkyl glycoside Chemical class 0.000 claims description 10
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 10
- 229940049964 oleate Drugs 0.000 claims description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
- 210000003022 colostrum Anatomy 0.000 claims description 8
- 235000021277 colostrum Nutrition 0.000 claims description 8
- 229930182470 glycoside Natural products 0.000 claims description 8
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 8
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 6
- 229960003471 retinol Drugs 0.000 claims description 6
- 235000020944 retinol Nutrition 0.000 claims description 6
- 239000011607 retinol Substances 0.000 claims description 6
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
- 229940032094 squalane Drugs 0.000 claims description 5
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 claims description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 4
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 claims description 4
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 claims description 4
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 4
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 4
- 241000764238 Isis Species 0.000 claims description 4
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 4
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 4
- 235000019774 Rice Bran oil Nutrition 0.000 claims description 4
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 4
- 229940022405 astaxanthin Drugs 0.000 claims description 4
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- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 claims description 4
- 239000001168 astaxanthin Substances 0.000 claims description 4
- 229940106189 ceramide Drugs 0.000 claims description 4
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 235000017471 coenzyme Q10 Nutrition 0.000 claims description 4
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 4
- 229940110767 coenzyme Q10 Drugs 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 4
- 229910021641 deionized water Inorganic materials 0.000 claims description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 4
- LBQIJVLKGVZRIW-ZDUSSCGKSA-N glabridin Chemical compound C1([C@H]2CC3=CC=C4OC(C=CC4=C3OC2)(C)C)=CC=C(O)C=C1O LBQIJVLKGVZRIW-ZDUSSCGKSA-N 0.000 claims description 4
- 229940093767 glabridin Drugs 0.000 claims description 4
- PMPYOYXFIHXBJI-ZDUSSCGKSA-N glabridin Natural products C1([C@H]2CC=3C=CC4=C(C=3OC2)CCC(O4)(C)C)=CC=C(O)C=C1O PMPYOYXFIHXBJI-ZDUSSCGKSA-N 0.000 claims description 4
- LBQIJVLKGVZRIW-UHFFFAOYSA-N glabridine Natural products C1OC2=C3C=CC(C)(C)OC3=CC=C2CC1C1=CC=C(O)C=C1O LBQIJVLKGVZRIW-UHFFFAOYSA-N 0.000 claims description 4
- 238000005417 image-selected in vivo spectroscopy Methods 0.000 claims description 4
- 238000012739 integrated shape imaging system Methods 0.000 claims description 4
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000913 palmityl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 4
- 229940016667 resveratrol Drugs 0.000 claims description 4
- 235000021283 resveratrol Nutrition 0.000 claims description 4
- 239000008165 rice bran oil Substances 0.000 claims description 4
- 229960005078 sorbitan sesquioleate Drugs 0.000 claims description 4
- UIVPNOBLHXUKDX-UHFFFAOYSA-N 3,5,5-trimethylhexyl 3,5,5-trimethylhexanoate Chemical compound CC(C)(C)CC(C)CCOC(=O)CC(C)CC(C)(C)C UIVPNOBLHXUKDX-UHFFFAOYSA-N 0.000 claims description 3
- 229940100554 isononyl isononanoate Drugs 0.000 claims description 3
- 229940048845 polyglyceryl-3 diisostearate Drugs 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 8
- 230000007794 irritation Effects 0.000 abstract description 4
- 239000012071 phase Substances 0.000 description 46
- 229920002385 Sodium hyaluronate Polymers 0.000 description 34
- 229940010747 sodium hyaluronate Drugs 0.000 description 34
- 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 34
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- 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 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229940014041 hyaluronate Drugs 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
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- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
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- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- SSISHJJTAXXQAX-ZETCQYMHSA-N L-ergothioneine Chemical compound C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC(=S)N1 SSISHJJTAXXQAX-ZETCQYMHSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
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- 229940124277 aminobutyric acid Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
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- 229940008099 dimethicone Drugs 0.000 description 1
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- WQXNXVUDBPYKBA-YFKPBYRVSA-N ectoine Chemical compound CC1=[NH+][C@H](C([O-])=O)CCN1 WQXNXVUDBPYKBA-YFKPBYRVSA-N 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
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- 229940093497 ergothioneine Drugs 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940099549 polyglycerin-3 Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
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Abstract
The invention discloses a multiple emulsion containing hyaluronic acid, a preparation method and application thereof. According to the invention, the hyaluronic acid composition is added into the multiple emulsion to be used as an external water phase of the W/O/W type emulsion, and the addition of the hyaluronic acid composition can improve the stability of the multiple emulsion and promote the absorption of active ingredients in the multiple emulsion; the active ingredient with irritation can be wrapped in the internal phase of multiple emulsion, and the addition of hyaluronic acid composition can effectively solve the irritation problem of cosmetics.
Description
Technical Field
The invention relates to the technical field of hyaluronic acid, in particular to a hyaluronic acid multiple emulsion with a stability improving effect, a preparation method and application thereof.
Background
The traditional emulsion has only two types of O/W type and W/O type. The W/O type emulsion has bright appearance and good moisturizing and skin moistening effects, but is easy to be sticky when being smeared, has poor skin feel and is not easy to clean; while the O/W type emulsion has good spreadability and refreshing skin feel, both the moisturizing effect and the skin moisturizing effect are inferior to those of the W/O type emulsion.
Multiple emulsions, which are multi-layer emulsions formed by dispersing one emulsion in another continuous phase, are generally highly dispersed, heterogeneous systems of varying particle size, of which there are many types, most commonly two types, W/O/W and O/W/O. Structurally, the multiple emulsion has a unique 'two-film three-phase' multi-compartment structure, such as a W/O/W type multiple emulsion, which comprises an external water phase, an oil phase and an internal water phase, wherein the oil phase wraps the internal water phase and is suspended in the external water phase to form the emulsion.
However, the multiple emulsion is limited in application to a certain extent because of its special "two-film three-phase" structure, which makes the multi-phase interface of the multiple emulsion have high interfacial energy, thus causing the emulsion to be easily broken and coalesced, and the emulsion to be delaminated after being stored for several weeks. At the same time, whether an active ingredient in a skin care product can exert its effect depends on whether the substance can reach a specific skin site. Therefore, it is important to promote the absorption of actives into the skin while maintaining the stability of multiple emulsions.
Disclosure of Invention
In view of the above problems, the present invention provides a multiple emulsion containing hyaluronic acid, which is of a W/O/W type, and in which a hyaluronic acid composition is added as an external aqueous phase, the stability of the multiple emulsion can be improved, and the transdermal absorption rate of the multiple emulsion can be promoted.
The specific technical scheme of the invention is as follows:
1. a multiple emulsion containing hyaluronic acid, the multiple emulsion comprising an oil phase, a W/O type emulsifier, an O/W type emulsifier, and a hyaluronic acid composition.
2. The multiple emulsion of claim 1, wherein the hyaluronic acid composition comprises hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof.
3. The multiple emulsion according to claim 2, wherein the hyaluronic acid or the salt thereof is 20 to 60%, preferably 25 to 40%, by mass in the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or its salt is 30-70%, preferably 40-55%.
4. A hyaluronic acid composition according to any of claims 1-3, wherein,
the molecular weight of the hyaluronic acid or the salt thereof is 100k-500kDa, preferably 150k-300kDa, and further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
5. The multiple emulsion according to any one of items 1 to 4, wherein the hyaluronic acid composition is 0.01 to 10%, preferably 0.05 to 2%, in terms of mass percentage in the multiple emulsion;
the oil phase is 20-50%, preferably 20-35%.
6. The multiple emulsion according to any one of claims 1 to 5, wherein the oil phase is selected from one or more of squalane, rice bran oil, GTCC, coconut oil and ISIS (isononyl isononanoate).
7. The multiple emulsion according to any one of claims 1 to 6, wherein the O/W type emulsifier is one or more selected from alkyl glycosides, polyglycerin-10 stearate, polyglycerin-10 oleate, and hydrogenated lecithin.
8. The multiple emulsion according to any one of items 1 to 7, wherein the W/O type emulsifier is one or more selected from polyglycerin-2 dipolyhydroxystearate, polyglycerin-2 oleate, polyglycerin-3 diisostearate, cetyl PEG/PPG-10/1 polydimethylsiloxane, sorbitan sesquioleate and PEG-20 glyceryl tristearate.
9. Multiple emulsion according to any one of claims 1 to 8, wherein the multiple emulsion further comprises an active ingredient, preferably the active ingredient has a molecular weight of < 1000Da, more preferably the active ingredient is present in an amount of 0.1 to 0.5% by mass of the multiple emulsion.
10. The multiple emulsion according to claim 9, wherein the active ingredient is one or more selected from the group consisting of glabridin, resveratrol, coenzyme Q10, astaxanthin, ceramide, and retinol.
11. A method of preparing the multiple emulsion of any one of items 1-10, comprising the steps of:
deionized water is used as phase A;
mixing the oil phase, W/O emulsifier and optional active ingredients to obtain phase B, and adding phase A into phase B to obtain W/O colostrum;
adding hyaluronic acid composition and O/W emulsifier into water, mixing to obtain phase C, and adding W/O colostrum into phase C to obtain multiple emulsion.
12. The method of item 11, wherein the multiple emulsion is a W/O/W type multiple emulsion.
13. Use of a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof and hydrolysed hyaluronic acid or a salt thereof in the cosmetic field, preferably in a multiple emulsion, further preferably in a multiple emulsion where improved stability is required.
14. The use according to item 13, wherein the hyaluronic acid or the salt thereof is 20 to 60%, preferably 25 to 40%, by mass of the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or its salt is 30-70%, preferably 40-55%.
15. The use according to claim 13 or 14, wherein the molecular weight of the hyaluronic acid or salt thereof is 100k-500kDa, preferably 150k-300kDa, further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the invention, the hyaluronic acid composition is added into the multiple emulsion to serve as an external water phase of the W/O/W type emulsion, so that the stability of the multiple emulsion can be improved and the absorption of active ingredients in the multiple emulsion can be promoted; the active ingredient with irritation can be wrapped in the internal phase of multiple emulsion, and the addition of hyaluronic acid composition can effectively solve the irritation problem of cosmetics.
Drawings
FIG. 1 is a photomicrograph of the multiple emulsion obtained in example 1
FIG. 2 is a graph showing skin retention in the penetration test conducted in Experimental example 3 using the multiple emulsion described in example 1 and the multiple emulsion described in comparative example 1.
Detailed Description
The present invention is described in detail in the following description of embodiments with reference to the figures, in which like numbers represent like features throughout the figures. While specific embodiments of the invention are shown in the drawings, it should be understood that the invention may be embodied in various forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.
It should be noted that certain terms are used throughout the description and claims to refer to particular components. As one skilled in the art will appreciate, various names may be used to refer to a component. This specification and claims do not intend to distinguish between components that differ in name but not function. In the following description and in the claims, the terms "include" and "comprise" are used in an open-ended fashion, and thus should be interpreted to mean "include, but not limited to. The description which follows is a preferred embodiment of the invention, however, the description is given for the purpose of illustrating the general principles of the invention and not for the purpose of limiting the scope of the invention. The scope of the present invention is defined by the appended claims.
The invention provides a multiple emulsion containing hyaluronic acid, which comprises an oil phase, a W/O type emulsifier, an O/W type emulsifier and a hyaluronic acid composition.
The W/O type emulsifier is a water-in-oil type emulsifier, and the O/W type emulsifier is an oil-in-water type emulsifier.
In one embodiment, the hyaluronic acid composition comprises hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof.
The acetylated hyaluronic acid or the salt thereof is obtained by acetylating hyaluronic acid or the salt thereof, and the acetylated hyaluronic acid or the salt thereof has lipophilicity due to introduction of acetyl.
The hydrolyzed hyaluronic acid or the salt thereof is oligomeric hyaluronic acid or the salt thereof produced by using an enzyme degradation technology, has smaller molecular weight, and is easier to be transdermally absorbed to epidermis and dermis.
In one embodiment, the hyaluronic acid or the salt thereof accounts for 20-60%, preferably 25-40% of the mass percentage of the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or its salt is 30-70%, preferably 40-55%.
For example, the hyaluronic acid or salt thereof may be 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, or any range therebetween, as a mass percentage in the hyaluronic acid composition;
the acetylated hyaluronic acid or salt thereof may be 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50% or any range therebetween;
the hydrolyzed hyaluronic acid or salt thereof may be 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, or any range therebetween.
In one embodiment, the molecular weight of the hyaluronic acid or salt thereof is 100k-500kDa, preferably 150k-300kDa, further preferably 210k-300 kDa; the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
For example, the hyaluronic acid or salt thereof may have a molecular weight of 100kDa, 110kDa, 120kDa, 130kDa, 140kDa, 150kDa, 160kDa, 170kDa, 180kDa, 190kDa, 200kDa, 210kDa, 220kDa, 230kDa, 240kDa, 250kDa, 260kDa, 270kDa, 280kDa, 290kDa, 300kDa, 350kDa, 400kDa, 450kDa, 500kDa, or any range therebetween;
the acetylated hyaluronic acid or salt thereof may have a molecular weight of 10kDa, 20kDa, 30kDa, 40kDa, 50kDa, 60kDa, 70kDa, 80kDa, 90kDa, 100kDa or any range therebetween;
the hydrolyzed hyaluronic acid or salt thereof may have a molecular weight of 0.8kDa, 0.9kDa, 1kDa, 2kDa, 3kDa, 4kDa, 5kDa, 6kDa, 7kDa, 8kDa, 9kDa, 10kDa, 11kDa, 12kDa, 13kDa, 14kDa, 15kDa, 16kDa, 17kDa, 18kDa, 19kDa, 20kDa, or any range therebetween.
The hyaluronate or acetylated hyaluronate or hydrolyzed hyaluronate refers to metal ion salts, such as sodium salt, potassium salt, calcium salt, zinc salt, etc., and is usually sodium salt.
In one embodiment, the hyaluronic acid composition is 0.01-10%, preferably 0.05-2%, by mass percentage in the multiple emulsion;
the oil phase is 20-50%, preferably 20-35%.
For example, the hyaluronic acid composition may be 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or any range therebetween, as a mass percentage in the multiple emulsion;
the oil phase may be 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, or any range therebetween.
The contents of the O/W type emulsifier and the W/O type emulsifier are not limited in the present invention, and they may be selected as needed as long as the functions of the present invention can be achieved.
In one embodiment, the oil phase is selected from one or more, for example two, three or four or more, of squalane, rice bran oil, GTCC, coconut oil, and ISIS.
GTCC is caprylic/capric triglyceride, which is an excellent moisturizing oil, has good spreadability, gives the skin a slippery but not greasy feel, and is easily absorbed by the skin. Has good effect on the uniformity and the fineness of cosmetics and can ensure that the skin is smooth and glossy.
In one embodiment, the O/W type emulsifier is selected from one or more than two of alkyl glycoside (APG1214), polyglycerin-10 stearate, polyglycerin-10 oleate and hydrogenated lecithin, for example, may be selected from two, three or four or more thereof.
The Alkyl glycoside is an Alkyl glycoside (APG) synthesized from glucose and fatty alcohol, and refers to a glycoside having a sugar unit of 2 or more in a complex glycoside compound, and is collectively referred to as Alkyl polyglycoside (or Alkyl polyglycoside). In general, the alkyl polyglycoside has a polymerization degree n of 1.1 to 3, and R is a C8 to C16 alkyl group. APG is white solid powder or light yellow oily liquid at normal temperature, has high solubility in water and is difficult to dissolve in common organic solvents.
In one embodiment, the W/O type emulsifier is selected from one or more than two of polyglyceryl-2 dipolyhydroxystearate, polyglyceryl-2 oleate, polyglyceryl-3 diisostearate, cetyl PEG/PPG-10/1 dimethicone, sorbitan sesquioleate, and PEG-20 glyceryl tristearate, for example, two, three, or four or more thereof.
In one embodiment, the multiple emulsion further comprises an active ingredient, preferably having a molecular weight of < 1000 Da.
The active ingredient may be any active ingredient known to those skilled in the art that can be used in skin care products or gel-type medical devices, and may be, for example, one or more, for example, two, three or more selected from glabridin, resveratrol, coenzyme Q10, astaxanthin, ceramide, retinol, ectoin, ergothioneine, aminobutyric acid, tranexamic acid and glutathione.
In one embodiment, the multiple emulsion comprises an oil phase, a W/O type emulsifier, an O/W type emulsifier, and a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof.
In one embodiment, the multiple emulsion comprises an oil phase, a W/O type emulsifier, an O/W type emulsifier, and a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof, the hyaluronic acid or a salt thereof being 20-60%, preferably 25-40%, by mass percentage in the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or its salt is 30-70%, preferably 40-55%.
In one embodiment, the multiple emulsion comprises an oil phase, a W/O type emulsifier, an O/W type emulsifier, and a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof, the hyaluronic acid or a salt thereof being 20-60%, preferably 25-40%, by mass percentage in the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or the salt thereof is 30-70%, preferably 40-55%, and the molecular weight of the hyaluronic acid or the salt thereof is 100k-500kDa, preferably 150k-300kDa, and further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
In one embodiment, the multiple emulsion comprises an oil phase, a W/O type emulsifier, an O/W type emulsifier, and a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof, the hyaluronic acid or a salt thereof being 20-60%, preferably 25-40%, by mass percentage in the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or the salt thereof is 30-70%, preferably 40-55%, and the molecular weight of the hyaluronic acid or the salt thereof is 100k-500kDa, preferably 150k-300kDa, and further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa;
the hyaluronic acid composition accounts for 0.01-10% of the multiple emulsion by mass percentage, and preferably 0.05-2%;
the oil phase is 20-50%, preferably 20-35%;
preferably, the oil phase is selected from one or more of squalane, rice bran oil, GTCC, coconut oil and ISIS (isononyl isononanoate);
preferably, the O/W type emulsifier is one or more than two of alkyl glycoside, polyglycerol-10 stearate, polyglycerol-10 oleate and hydrogenated lecithin;
preferably, the W/O type emulsifier is one or more selected from polyglyceryl-2 dipolyhydroxystearate, polyglyceryl-2 oleate, polyglyceryl-3 diisostearate, cetyl PEG/PPG-10/1 polydimethylsiloxane, sorbitan sesquioleate and PEG-20 glyceryl tristearate;
preferably, the multiple emulsion further comprises an active ingredient, preferably, the molecular weight of the active ingredient is less than 1000Da, and further preferably, the active ingredient accounts for 0.1-0.5% of the multiple emulsion by mass percentage;
preferably, the active ingredient is one or more selected from glabridin, resveratrol, coenzyme Q10, astaxanthin, ceramide and retinol;
the multiple emulsion provided by the invention adopts the hyaluronic acid composition as the external water phase of the multiple emulsion, can provide the stability of the multiple emulsion, and can promote the transdermal absorption of the multiple emulsion.
The invention provides a method for preparing the multiple emulsion, which comprises the following steps:
taking water as an A phase;
mixing the oil phase, W/O emulsifier and optional active ingredients to obtain phase B, and adding phase A into phase B to obtain W/O colostrum;
adding hyaluronic acid composition and O/W emulsifier into water, mixing to obtain phase C, and adding W/O colostrum into phase C to obtain multiple emulsion.
In one embodiment, the multiple emulsion is a W/O/W type multiple emulsion.
The present invention provides the use of a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof and hydrolysed hyaluronic acid or a salt thereof in the cosmetic field, preferably in a multiple emulsion, further preferably in a multiple emulsion where improved stability is required.
In one embodiment, the hyaluronic acid or the salt thereof accounts for 20-60%, preferably 25-40% of the mass percentage of the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or its salt is 30-70%, preferably 40-55%.
In one embodiment, the molecular weight of the hyaluronic acid or salt thereof is 100k-500kDa, preferably 150k-300kDa, further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
The inventors have creatively invented a method for improving the stability of multiple emulsions in the course of experiments, which can improve the stability of multiple emulsions and also can promote the transdermal absorption of multiple emulsions by adding a hyaluronic acid composition to multiple emulsions.
Examples
The invention is described generally and/or specifically for the materials used in the tests and the test methods, in the following examples,% means wt%, i.e. percent by weight, unless otherwise specified. The reagents or instruments are not indicated by manufacturers, and are all conventional reagent products commercially available, wherein hyaluronic acid or its salt, acetylated hyaluronic acid or its salt, and hydrolyzed hyaluronic acid or its salt are all available from Huaxi Biotechnology Ltd.
Example 1
(1) And starting the constant-temperature water bath kettle, maintaining the temperature at 40-50 ℃, taking a proper amount of deionized water into the beaker A, and preheating the beaker A in the constant-temperature water bath kettle to obtain the phase A.
(2) Weighing squalane, polyglycerol-2 oleate and retinol in a beaker B, uniformly stirring, and preheating in a constant-temperature water bath to obtain a phase B.
(3) Adding phase A to phase B to obtain W/O colostrum.
(4) Weighing deionized water, a hyaluronic acid composition and polyglycerol-10 stearate, mixing in a beaker C to obtain a C phase, adding W/O colostrum into the C phase, and uniformly stirring to obtain a W/O/W multiple emulsion, wherein the contents of the components are shown in Table 1, sodium hyaluronate with the molecular weight of 150kDa accounts for 25%, sodium acetylated hyaluronate with the molecular weight of 10kDa accounts for 40%, and sodium hydrolyzed hyaluronate with the molecular weight of 15kDa accounts for 35% by mass of hyaluronic acid, and a microscope schematic diagram of the obtained multiple emulsion is shown in figure 1.
Examples 2 to 13
Examples 2 to 13 multiple emulsions were prepared according to the method of example 1, wherein the contents of the respective components are shown in table 1, and sodium hyaluronate with a molecular weight of 150kDa was 25%, sodium acetylated hyaluronate with a molecular weight of 10kDa was 40%, and sodium hydrolyzed hyaluronate with a molecular weight of 15kDa was 35% in mass percentage of hyaluronic acid.
Example 14
Example 14 multiple emulsions were prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% by mass of sodium hyaluronate with a molecular weight of 150kDa, 20% by mass of sodium hyaluronate with a molecular weight of 10kDa, and 55% by mass of sodium hyaluronate with a molecular weight of 15kDa, based on the mass percentage of the hyaluronic acid composition.
Example 15
Example 15 multiple emulsions were prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% by mass of sodium hyaluronate with a molecular weight of 150kDa, 20% by mass of sodium hyaluronate with a molecular weight of 10kDa, and 55% by mass of sodium hyaluronate with a molecular weight of 15 kDa.
Example 16
Example 16 multiple emulsions were prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% sodium hyaluronate with a molecular weight of 150kDa, 25% sodium hyaluronate with a molecular weight of 10kDa, and 50% sodium hyaluronate with a molecular weight of 15kDa, in mass percentage in the hyaluronic acid composition.
Example 17
Example 17 multiple emulsions were prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% sodium hyaluronate with a molecular weight of 210kDa, 40% sodium hyaluronate with a molecular weight of 20kDa, and 35% sodium hyaluronate with a molecular weight of 10kDa, in mass percentage in the hyaluronic acid composition.
Example 18
Example 18 a multiple emulsion was prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% by mass of sodium hyaluronate with a molecular weight of 300kDa, 40% by mass of sodium hyaluronate with a molecular weight of 30kDa, and 35% by mass of sodium hyaluronate with a molecular weight of 3 kDa.
Example 19
Example 19 a multiple emulsion was prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% by mass of sodium hyaluronate with a molecular weight of 300kDa, 40% by mass of sodium hyaluronate with a molecular weight of 50kDa, and 35% by mass of sodium hyaluronate with a molecular weight of 15 kDa.
Example 20
Example 20 multiple emulsions were prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% by mass of sodium hyaluronate with a molecular weight of 100kDa, 40% by mass of sodium hyaluronate with a molecular weight of 10kDa, and 35% by mass of sodium hyaluronate with a molecular weight of 20 kDa.
Example 21
Example 21 a multiple emulsion was prepared according to the method of example 1, with the same composition as in example 1, except that the content of each sodium hyaluronate in the hyaluronic acid composition was different, 25% by mass of sodium hyaluronate with a molecular weight of 500kDa, 40% by mass of sodium hyaluronate with a molecular weight of 100kDa, and 35% by mass of sodium hyaluronate with a molecular weight of 0.8kDa, based on the mass percentage of the hyaluronic acid composition.
Comparative examples 1 to 3
Comparative examples 1 to 3 the resulting multiple emulsions were prepared according to the method described in example 1, wherein the contents of the respective components are shown in table 1.
Of these, comparative example 3 is different from example 1 in that comparative example 3 uses only acetylated hyaluronic acid, and example 1 is a multiple emulsion obtained using a hyaluronic acid composition.
TABLE 1 table of contents of components in examples and comparative examples
Experimental example 1 stability test
High-temperature test: placing the sample to be tested in a proper clean container, placing the container at the temperature of 55 ℃ for 10 days, sampling on the 5 th day and the 10 th day, and observing the layering condition of the sample.
And (3) low-temperature test: placing the sample to be tested in a proper clean container, placing the container for 5 days at the temperature of minus 20 ℃, sampling on the 5 th day, and observing the layering condition of the sample.
Centrifugal stability: the centrifuge tube was filled with the sample to be tested at about 2/3 height and stoppered. Then placing into an electric heating constant temperature incubator pre-adjusted to 38 ℃, keeping for 1h, immediately transferring into a centrifuge, adjusting the centrifuge to a centrifugal speed of 2000r/min, rotating for 30min, taking out and observing.
The test results are shown in table 2 below, and it can be seen from the data in table 2 that the addition of the hyaluronic acid composition has an important effect on the stability of the multiple emulsion. The multiple emulsion without the hyaluronic acid composition is placed at room temperature, is poor in heat resistance, cold resistance and centrifugal stability, and the stability of the multiple emulsion is obviously improved after the hyaluronic acid composition is added.
TABLE 2 Heat and Cold resistance and centrifugal stability test results
Experimental example 2 Patch test
Tearing the packaging of the spot tester, and measuring 0.025mL or 0.025g of the prepared sample to be added into a chamber. The patch tester is applied to the curved side of the forearm of the subject and gently pressed with the palm to be uniformly applied to the skin for 24 h.
The reaction results were recorded at 30min, 24h and 48h after removal of the plaque tester as observed in Table 4. The results are shown in Table 5.
TABLE 3 skin response grading Standard for skin Enclosed Patch test
TABLE 4 Patch test results
As can be seen from the results in Table 4, the multiple emulsions obtained according to the present invention are less irritating and show substantially or very little irritating reactions.
Experimental example 3 penetration-promoting test
Franz diffusion cell permeation experiments were performed on example 1 (test substance) and comparative example 1 (control) to explore the penetration promoting effect of hyaluronic acid compositions on the active substance (retinol). The in vitro pigskin is fixed between a supply pool and a receiving pool of a Phoenix DB-6 transdermal test system, about 16ml of receiving liquid is added into a sampling tube according to the liquid height of the sampling tube, and air is exhausted, so that the skin dermis layer is in close contact with the receiving liquid. Then 49. mu.l of 15% (m/v) of the sample to be tested was added to the skin surface, and the sample was spread evenly from the center of the skin to the edge by a stainless steel stirring rod. Each sample was replicated in 3 replicates and was uniformly stirred while maintaining a constant temperature water bath at (32. + -. 1). degree.C.at a speed of 300 rpm/min. After 20h of diffusion, the samples on the surface of the pigskin, in the skin and in the receiving liquid were collected and examined by high performance liquid chromatography to examine the in vitro transdermal effect of the different samples, the results of which are shown in fig. 2 and table 5.
Calculation method
Skin-in-skin retention ratio (part of the detected amount in skin of test substance/part of the detected amount in skin of control substance)
TABLE 5 Retention ratio in skin test results
As can be seen from table 5 and fig. 2, at node 20h, the retention of the active substance in the skin was improved by 28% after the addition of the hyaluronic acid composition, compared to the group without the addition of the hyaluronic acid composition. This demonstrates that the hyaluronic acid composition can promote retention of the active substance and thus further promote transdermal absorption of the active substance by the skin.
In summary, the hyaluronic acid composition is added into the multiple emulsion, so that the stability of the multiple emulsion can be improved, the multiple emulsion is stable at low temperature and high temperature, no obvious layering occurs, and the absorption of active ingredients in the multiple emulsion can be promoted.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are still within the protection scope of the technical solution of the present invention.
Claims (10)
1. A multiple emulsion containing hyaluronic acid, the multiple emulsion comprising an oil phase, a W/O type emulsifier, an O/W type emulsifier, and a hyaluronic acid composition.
2. The multiple emulsion of claim 1, wherein the hyaluronic acid composition comprises hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof, and hydrolyzed hyaluronic acid or a salt thereof.
3. The multiple emulsion according to claim 2, wherein the hyaluronic acid or the salt thereof is 20 to 60%, preferably 25 to 40%, by mass percentage in the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or salt thereof is 30-70%, preferably 40-55%;
preferably, the molecular weight of the hyaluronic acid or the salt thereof is 100k-500kDa, preferably 150k-300kDa, and further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
4. The multiple emulsion according to any one of claims 1 to 3, wherein the hyaluronic acid composition is 0.01 to 10%, preferably 0.05 to 2%;
the oil phase is 20-50%, preferably 20-35%.
5. The multiple emulsion according to any one of claims 1 to 4, wherein the oil phase is selected from one or more of squalane, rice bran oil, GTCC, coconut oil and ISIS (isononyl isononanoate);
preferably, the O/W type emulsifier is one or more than two of alkyl glycoside, polyglycerol-10 stearate, polyglycerol-10 oleate and hydrogenated lecithin;
preferably, the W/O type emulsifier is one or more selected from polyglyceryl-2 dipolyhydroxystearate, polyglyceryl-2 oleate, polyglyceryl-3 diisostearate, cetyl PEG/PPG-10/1 polydimethylsiloxane, sorbitan sesquioleate and PEG-20 glyceryl tristearate.
6. The multiple emulsion according to any one of claims 1 to 5, wherein the multiple emulsion further comprises an active ingredient, preferably the active ingredient has a molecular weight of < 1000Da, further preferably the active ingredient is 0.1-0.5% by mass of the multiple emulsion;
preferably, the active ingredient is one or more selected from glabridin, resveratrol, coenzyme Q10, astaxanthin, ceramide and retinol.
7. A method of preparing the multiple emulsion of any one of claims 1-6, comprising the steps of:
deionized water is used as phase A;
mixing the oil phase, W/O emulsifier and optional active ingredients to obtain phase B, and adding phase A into phase B to obtain W/O colostrum;
adding hyaluronic acid composition and O/W emulsifier into water, mixing to obtain phase C, and adding W/O colostrum into phase C to obtain multiple emulsion.
8. The method of claim 7, wherein the multiple emulsion is a W/O/W type multiple emulsion.
9. Use of a hyaluronic acid composition comprising hyaluronic acid or a salt thereof, acetylated hyaluronic acid or a salt thereof and hydrolysed hyaluronic acid or a salt thereof in the cosmetic field, preferably in a multiple emulsion, further preferably in a multiple emulsion where improved stability is required.
10. The use according to claim 9, wherein the hyaluronic acid or the salt thereof is 20-60%, preferably 25-40% by mass of the hyaluronic acid composition;
the content of the acetylated hyaluronic acid or the salt thereof is 10-50%, and the preferable content is 20-35%;
the hydrolyzed hyaluronic acid or salt thereof is 30-70%, preferably 40-55%;
preferably, the molecular weight of the hyaluronic acid or the salt thereof is 100k-500kDa, preferably 150k-300kDa, and further preferably 210k-300 kDa;
the molecular weight of the acetylated hyaluronic acid or the salt thereof is 10k-100kDa, preferably 10k-50kDa, and more preferably 20k-30 kDa; and
the molecular weight of the hydrolyzed hyaluronic acid or the salt thereof is 0.8k-20kDa, preferably 3k-15kDa, and more preferably 3k-10 kDa.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104135999A (en) * | 2012-02-28 | 2014-11-05 | 三得利控股株式会社 | W/o/w emulsion having long-term stability and method for producing same |
| CN109199878A (en) * | 2018-09-26 | 2019-01-15 | 华南理工大学 | A kind of whitening sun protection W/O/W multiple emulsion and preparation method thereof |
| JP2019006725A (en) * | 2017-06-27 | 2019-01-17 | 日本精化株式会社 | Hyaluronic acid production promoter and cosmetics containing the same |
| JP2020158400A (en) * | 2019-03-25 | 2020-10-01 | 日本精化株式会社 | O/w emulsion composition |
| CN111728883A (en) * | 2020-07-07 | 2020-10-02 | 上海舒彩网络科技有限公司 | Cleansing oil emulsified to form multi-structure emulsion (W/O/W) and preparation method thereof |
| CN112957277A (en) * | 2021-02-06 | 2021-06-15 | 武汉百思凯瑞生物科技有限公司 | Multiple hyaluronic acid nano composition and preparation method and application thereof |
| CN113730296A (en) * | 2020-05-27 | 2021-12-03 | 玫琳凯有限公司 | Topical compositions and methods |
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- 2021-12-28 CN CN202111631995.8A patent/CN114288205A/en active Pending
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| CN104135999A (en) * | 2012-02-28 | 2014-11-05 | 三得利控股株式会社 | W/o/w emulsion having long-term stability and method for producing same |
| JP2019006725A (en) * | 2017-06-27 | 2019-01-17 | 日本精化株式会社 | Hyaluronic acid production promoter and cosmetics containing the same |
| CN109199878A (en) * | 2018-09-26 | 2019-01-15 | 华南理工大学 | A kind of whitening sun protection W/O/W multiple emulsion and preparation method thereof |
| JP2020158400A (en) * | 2019-03-25 | 2020-10-01 | 日本精化株式会社 | O/w emulsion composition |
| CN113730296A (en) * | 2020-05-27 | 2021-12-03 | 玫琳凯有限公司 | Topical compositions and methods |
| CN111728883A (en) * | 2020-07-07 | 2020-10-02 | 上海舒彩网络科技有限公司 | Cleansing oil emulsified to form multi-structure emulsion (W/O/W) and preparation method thereof |
| CN112957277A (en) * | 2021-02-06 | 2021-06-15 | 武汉百思凯瑞生物科技有限公司 | Multiple hyaluronic acid nano composition and preparation method and application thereof |
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