KR20230001874A - Surface modified retinoid immersion porous silica - Google Patents
Surface modified retinoid immersion porous silica Download PDFInfo
- Publication number
- KR20230001874A KR20230001874A KR1020210084952A KR20210084952A KR20230001874A KR 20230001874 A KR20230001874 A KR 20230001874A KR 1020210084952 A KR1020210084952 A KR 1020210084952A KR 20210084952 A KR20210084952 A KR 20210084952A KR 20230001874 A KR20230001874 A KR 20230001874A
- Authority
- KR
- South Korea
- Prior art keywords
- retinoid
- porous silica
- polyethoxylated
- supported
- modified
- Prior art date
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 214
- 239000000377 silicon dioxide Substances 0.000 title claims abstract description 104
- 150000004492 retinoid derivatives Chemical class 0.000 title claims abstract description 86
- 238000007654 immersion Methods 0.000 title 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000002537 cosmetic Substances 0.000 claims abstract description 20
- 229910000077 silane Inorganic materials 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims description 42
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 claims description 6
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 6
- 238000002845 discoloration Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
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- 239000003795 chemical substances by application Substances 0.000 claims description 4
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000516 sunscreening agent Substances 0.000 claims description 3
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 claims description 3
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 claims description 3
- MLXDKRSDUJLNAB-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MLXDKRSDUJLNAB-UHFFFAOYSA-N 0.000 claims description 3
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 claims description 2
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- 229920002545 silicone oil Polymers 0.000 claims description 2
- MASNVFNHVJIXLL-UHFFFAOYSA-N ethenyl(ethoxy)silicon Chemical compound CCO[Si]C=C MASNVFNHVJIXLL-UHFFFAOYSA-N 0.000 claims 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims 2
- 150000004756 silanes Chemical class 0.000 claims 1
- 239000012730 sustained-release form Substances 0.000 abstract description 9
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- 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 description 16
- 230000037384 skin absorption Effects 0.000 description 12
- 231100000274 skin absorption Toxicity 0.000 description 12
- 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 description 11
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- 229960003471 retinol Drugs 0.000 description 5
- 235000020944 retinol Nutrition 0.000 description 5
- 239000011607 retinol Substances 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 4
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- -1 lipid peroxides Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
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- 238000000338 in vitro Methods 0.000 description 3
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- 239000012756 surface treatment agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 150000004347 all-trans-retinol derivatives Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- BIVBRWYINDPWKA-VLQRKCJKSA-L Glycyrrhizinate dipotassium Chemical compound [K+].[K+].O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H]1CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)C)C(O)=O)C([O-])=O)[C@@H]1O[C@H](C([O-])=O)[C@@H](O)[C@H](O)[C@H]1O BIVBRWYINDPWKA-VLQRKCJKSA-L 0.000 description 1
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- 229920002701 Polyoxyl 40 Stearate Polymers 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
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- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
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- FRDGQNBJYVOCMQ-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound C(=C)[Si](OCC)(OCC)OCC.C(=C)[Si](OCC)(OCC)OCC FRDGQNBJYVOCMQ-UHFFFAOYSA-N 0.000 description 1
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 239000000344 soap Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 229950011392 sorbitan stearate Drugs 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
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Images
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
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- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
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- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
본 발명은 안정성 및 안전성이 개선된 저자극의 표면 개질된 레티노이드 담지 다공성 실리카에 관한 것이다.The present invention relates to a hypoallergenic surface-modified retinoid-supported porous silica with improved stability and safety.
비타민 A 혹은 그 유도체는 현재까지 알려진 노화피부 개선의 대표적인 물질이며 이들을 함유한 제품이 많이 판매되고 있다. 비타민 A 혹은 그 유도체는 피부내 섬유아세포의 증식 및 콜라겐 합성을 증식 시키는 것으로 알려져 있으며, 주름 기능성 화장품의 유효성분으로 다양하게 활용되고 있다. 하지만 비타민 A는 지용성으로 빛, 산소, 열, 지질과산화물에 의하여 불안정하는 단점이 있어 안정화 기술이 필수적이며, 제품 개발시에 용기 또한 빛과 산소가 차단되는 용기를 사용 하여야 안정성을 확보할 수 있다. 또한 과량의 비타민 A 혹은 그 유도체는 햇빛에 의해서 피부 감수성을 증가시킬 수 있는 물질이다. 소비자가 비티민 A 혹은 그 유도체가 포함되는 화장품을 사용할 경우 피부에서 피부 붉어짐, 홍반, 따가움, 간지러움 등의 다양한 형태로 피부에 발현하게 된다.Vitamin A or a derivative thereof is a representative material for improving aging skin known to date, and many products containing them are sold. Vitamin A or its derivatives are known to increase the proliferation of fibroblasts and collagen synthesis in the skin, and are widely used as active ingredients in wrinkle functional cosmetics. However, since vitamin A is fat-soluble, it has the disadvantage of being unstable by light, oxygen, heat, and lipid peroxides, so stabilization technology is essential. In addition, excessive vitamin A or its derivatives are substances that can increase skin sensitivity to sunlight. When consumers use cosmetics containing vitamin A or its derivatives, various forms of skin redness, erythema, stinging, and itching appear on the skin.
이러한 비타민 A 및 그 유도체의 안정성 및 안전성 개선을 위해서 등록특허 (10-1314100) 등에서 리포좀 등의 다양한 약물전달시스템을 이용하여 안정성/안전성을 개선하기 위해서 노력하고 있다. 하지만 이러한 약물전달지지체는 유효성분의 담지 효율이 현저히 낮을 뿐만 아니라, 화장품 제형 내에서 다른 보조 성분 및 제형 제조공정 중에서 약물전달지지체의 형태가 일시적으로 붕괴 혹은 일부가 붕괴되는 현상이 발생하게 된다. 그에 따라 레티노이드의 안정성 개선 효과가 크지 못하며, 서방형 방출로 야기되는 안전성 개선효과 또한 여전히 미흡하다.In order to improve the stability and safety of vitamin A and its derivatives, efforts are being made to improve stability/safety by using various drug delivery systems such as liposomes in the registered patent (10-1314100). However, these drug delivery scaffolds not only have significantly low carrying efficiency of active ingredients, but also temporarily collapse or partially collapse the shape of the drug delivery scaffold during the manufacturing process of other auxiliary ingredients and formulations in the cosmetic formulation. Accordingly, the effect of improving the stability of retinoids is not great, and the effect of improving safety caused by the sustained-release type is still insufficient.
본 발명의 목적은 안정성/안전성이 개선된 저자극의 레티노이드 담지 다공성 실리카 및 이의 제조방법을 제공하는 것이다.An object of the present invention is to provide a hypoallergenic retinoid-supported porous silica with improved stability/safety and a method for preparing the same.
본 발명의 다른 목적은 상기 저자극의 레티노이드 담지 다공성 실리카를 포함하는 화장료 조성물을 제공하는 것이다.Another object of the present invention is to provide a cosmetic composition comprising the hypoallergenic retinoid-supporting porous silica.
상기 목적을 달성하기 위하여, 본 발명은 폴리에톡실화된 레티노이드가 담지되고, 실란계 화합물에 의해 표면 개질된 레티노이드 담지 다공성 실리카를 제공한다.In order to achieve the above object, the present invention provides a retinoid-supported porous silica loaded with polyethoxylated retinoid and surface-modified with a silane-based compound.
본 발명은 또한 폴리에톡실화된 레티노이드 용액 및 다공성 실리카를 혼합하여 다공성 실리카 내에 폴리에톡실화된 레티노이드를 담지하는 단계; 및The present invention also includes the steps of supporting the polyethoxylated retinoid in the porous silica by mixing the polyethoxylated retinoid solution and the porous silica; and
폴리에톡실화된 레티노이드가 담지된 다공성 실리카 및 실란계 화합물을 반응시켜 다공성 실리카의 표면을 개질하는 단계를 포함하는 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법을 제공한다.Provided is a method for producing a surface-modified retinoid-supported porous silica comprising the step of modifying the surface of the porous silica by reacting the porous silica supported with polyethoxylated retinoid and a silane-based compound.
본 발명은 또한 상기의 표면 개질된 레티노이드 담지 다공성 실리카를 포함하는 화장료 조성물을 제공한다.The present invention also provides a cosmetic composition comprising the surface-modified retinoid-supporting porous silica.
본 발명은 폴리에톡실화된 형태의 레티노이드를 다공성 실리카에 담지한 후 실란계 화합물로 표면 처리함으로써 레티노이드의 담지 효율을 높이고, 서방성 방출 효율을 개선하여 안정성과 안전성이 개선된 기능성 화장품의 유효성분으로 활용할 수 있다.The present invention increases the loading efficiency of retinoid by loading polyethoxylated retinoid on porous silica and then treating the surface with a silane-based compound, and improves the sustained-release efficiency to improve the stability and safety of functional cosmetics. can be utilized as
도 1은 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카의 제조공정을 도시한 것이다.
도 2는 프란쯔 확산 셀(Franze diffusion cell)을 이용한 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카의 O/W(수중유형, Oil in Water type) 제형에서의 레티노이드 방출 거동 실험 결과를 나타낸 것으로, 제형 생체외 피부 흡수 실험 결과이다.
도 3은 프란쯔 확산 셀(Franze diffusion cell)을 이용한 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카의 O/W 제형에서의 레티노이드 방출 거동 실험 결과를 나타낸 것으로, 제형 적용 시간별 피부 흡수량 결과이다.
도 4는 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카의 생체내 소비자 품평 테스트 결과이다.1 shows a manufacturing process of the surface-modified retinoid-supported porous silica of the present invention.
Figure 2 shows the results of experiments on retinoid release behavior in an O/W (Oil in Water type) formulation of the surface-modified retinoid-supported porous silica of the present invention using a Franze diffusion cell. This is the result of in vitro skin absorption test.
FIG. 3 shows the results of an experiment on retinoid release behavior in an O/W formulation of the surface-modified retinoid-supported porous silica of the present invention using a Franze diffusion cell, showing the results of skin absorption by time of application of the formulation.
4 is a result of an in vivo consumer evaluation test of the surface-modified retinoid-supported porous silica of the present invention.
이하, 본 발명의 구성을 구체적으로 설명한다.Hereinafter, the configuration of the present invention will be described in detail.
본 발명은 폴리에톡실화된 레티노이드가 담지되고, 실란계 화합물에 의해 표면 개질된 레티노이드 담지 다공성 실리카에 관한 것이다.The present invention relates to a retinoid-supported porous silica loaded with polyethoxylated retinoid and surface-modified with a silane-based compound.
본 발명은 비타민 A 유도체인 레티노이드의 1) 안정성을 개선하기 위해 화장품 제형내에서 다른 성분들에 의해서 분해/변성이 쉽지 일어나지 않으며, 레티노이드류의 빛/산소의 노출을 감소시켜 안정성을 향상시킬 수 있으며, 다른 약물전달지지체 대비하여 고함량의 레티노이드를 담지할 수 있는 장점을 담체로 다공성 실리카를 사용하며, 2) 레티노이드 안전성을 개선하기 위해 다공성 실리카 표면을 실란계 화합물로 표면 처리함으로써 서방형으로 레티노이드를 용출시키는 것을 특징으로 한다.In order to improve the stability of retinoids, which are vitamin A derivatives, the present invention is not easily decomposed/denatured by other ingredients in cosmetic formulations, and the stability can be improved by reducing the exposure of retinoids to light/oxygen. Compared to other drug delivery scaffolds, porous silica is used as a carrier for the advantage of carrying a high content of retinoid. 2) To improve the safety of retinoid, the surface of the porous silica is treated with a silane-based compound to release retinoid in a sustained release form. It is characterized by elution.
본 발명의 일 구체예에 따르면, 레티노이드의 방출 거동은 O/W 제형에 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카와 다공성 실리카에 담지하지 않은 레티노이드를 프란쯔 확산 셀(Franze diffusion cell)을 이용하여 비교하였고, 레티노이드의 안전성을 비교하기 위해서는 표면 개질된 레티노이드 담지 다공성 실리카 파우더의 HET-CAM 테스트 및 소비자 품평을 통해서 자극 지수를 확인하였다. 그 결과, 25℃ 및 40℃에서 표면 개질된 레티노이드 담지 다공성 실리카 파우더 적용 제형은 16주에서도 안정하였으며, 실란계 화합물의 농도 의존적으로 레티노이드 용출량이 감소하여 레티노이드를 서서히 용출시킴으로써 서방형 제제로서의 응용 가능성을 확인하였다.According to one embodiment of the present invention, the release behavior of the retinoid is measured by using the surface-modified retinoid-supported porous silica of the present invention and the retinoid not loaded on the porous silica in an O/W formulation using a Franze diffusion cell. In order to compare the safety of the retinoids, the stimulation index was confirmed through the HET-CAM test and consumer reviews of the surface-modified retinoid-supported porous silica powder. As a result, the surface-modified retinoid-supported porous silica powder application formulation at 25 ° C and 40 ° C was stable even after 16 weeks, and the retinoid elution amount decreased in a concentration-dependent manner of the silane-based compound, thereby slowly dissolving the retinoid, thereby increasing the possibility of application as a sustained-release preparation. Confirmed.
상기 폴리에톡실화된 레티노이드는 폴리에톡실레이티드 레틴아마이드(polyethoxylated retinamide)를 사용할 수 있다.As the polyethoxylated retinoid, polyethoxylated retinamide may be used.
상기 다공성 실리카는 1 내지 50 ㎛의 직경 크기를 가질 수 있다.The porous silica may have a diameter of 1 to 50 μm.
상기 실란계 화합물은 트리에톡시카프릴릴실란(Triethoxycaprylylsilane), 아미노프로필트라이에톡시실레인(Aminopropyl Triethoxysilane), 글라이시독시프로필트라이메톡시실란(Glycidoxypropyl Trimethoxysilane), 아이소뷰틸트리에톡시실레인(Isobutyltriethoxysilane), 퍼플루오로옥틸에틸트라이에톡시실레인(Perfluorooctylethyl Triethoxysilane), 퍼플루오로옥틸트라이에톡시실레인(Perfluorooctyl Triethoxysilane), 스테아릴트라이에톡시실레인(Stearyl Triethoxysilane), 메틸트라이에톡시실레인(Methyltriethoxysilane), 피이지-8 메틸에터트라이에톡시실레인(PEG-8 Methyl Ether Triethoxysilane), 비닐에톡시실레인(Vinyltriethoxysilane) 등을 단독 또는 2종 이상 사용할 수 있다.The silane-based compound is triethoxycaprylylsilane, aminopropyl triethoxysilane, glycidoxypropyl trimethoxysilane, isobutyltriethoxysilane ), Perfluorooctylethyl Triethoxysilane, Perfluorooctyl Triethoxysilane, Stearyl Triethoxysilane, Methyltriethoxysilane (Methyltriethoxysilane), PEG-8 Methyl Ether Triethoxysilane (PEG-8 Methyl Ether Triethoxysilane), and vinyltriethoxysilane (Vinyltriethoxysilane) may be used alone or in combination of two or more.
본 발명은 또한 폴리에톡실화된 레티노이드 용액 및 다공성 실리카를 혼합하여 다공성 실리카 내에 폴리에톡실화된 레티노이드를 담지하는 단계; 및The present invention also includes the steps of supporting the polyethoxylated retinoid in the porous silica by mixing the polyethoxylated retinoid solution and the porous silica; and
폴리에톡실화된 레티노이드가 담지된 다공성 실리카 및 실란계 화합물을 반응시켜 다공성 실리카의 표면을 개질하는 단계를 포함하는 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법에 관한 것이다.A method for preparing a surface-modified retinoid-supported porous silica comprising the step of modifying the surface of the porous silica by reacting the porous silica supported with polyethoxylated retinoid and a silane-based compound.
본 발명의 표면 개질된 레티노이드 담지 다공성 실리카는 페길화에 의해 친수부를 갖는 레티노이드를 다공성 실리카에 담지시킨 후 열처리를 통해 소수성의 실란계 화합물로 표면 코팅함으로써 제조되는 것을 특징으로 한다.The surface-modified retinoid-supported porous silica of the present invention is characterized in that it is prepared by carrying a retinoid having a hydrophilic part on the porous silica by pegylation and then coating the surface with a hydrophobic silane-based compound through heat treatment.
본 발명의 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법을 단계별로 구체적으로 설명하면 다음과 같다.The step-by-step method for preparing the surface-modified retinoid-supported porous silica of the present invention will be described in detail.
제1단계는 폴리에톡실화된 레티노이드를 다공성 실리카에 담지시키는 단계이다.The first step is to support the polyethoxylated retinoid on porous silica.
이를 위해 우선 폴리에톡실화된 레티노이드를 광 차단 조건에서 용매에 고르게 용해시켜 레티노이드 용액을 제조한다.To this end, a retinoid solution is prepared by uniformly dissolving the polyethoxylated retinoid in a solvent under light blocking conditions.
상기 폴리에톡실화된 레티노이드는 표면 개질된 레티노이드 담지 다공성 실리카 100 중량%에 대해 0.5 내지 20 중량%, 더 구체적으로 5 내지 15 중량%로 혼합될 수 있다. 상기 범위를 벗어날 경우, 다공성 실리카 내에 담지되지 않고 잔류하는 레티노이드 함량이 늘어나 경제성이 떨어질 수 있다.The polyethoxylated retinoid may be mixed in an amount of 0.5 to 20 wt%, more specifically 5 to 15 wt%, based on 100 wt% of the surface-modified retinoid-supported porous silica. If it is out of the above range, the content of retinoid remaining without being supported in the porous silica increases, and economic feasibility may decrease.
상기 용매는 메탄올 또는 에탄올을 사용할 수 있다. 상기 용매의 함량은 레티노이드의 함량에 따라 당업자 수준에서 적절히 조절될 수 있어 특별히 제한하지는 않는다.As the solvent, methanol or ethanol may be used. The amount of the solvent may be appropriately adjusted by those skilled in the art according to the content of the retinoid and is not particularly limited.
상기 레티노이드 용액 제조 시 필요에 따라 하이드로카본계 오일, 에스터 오일, 천연오일, 실리콘 오일, 항산화제, 광안정성제, 항염제, 변색방지제, 자외선 차단제, 염료, 안료 등으로 등을 추가로 첨가할 수 있다. When preparing the retinoid solution, hydrocarbon oil, ester oil, natural oil, silicone oil, antioxidant, light stabilizer, anti-inflammatory agent, anti-discoloration agent, sunscreen, dye, pigment, etc. may be additionally added as needed. .
다음으로, 다공성 실리카에 폴리에톡실화된 레티노이드 용액을 서서히 투입하여 믹서, 예컨대 헨셀믹서 등을 이용하여 상온에서 10분 이상 동안 고르게 섞어준다.Next, the polyethoxylated retinoid solution is gradually added to the porous silica and mixed evenly at room temperature for 10 minutes or more using a mixer, such as a Henschel mixer.
상기 다공성 실리카는 1 내지 50 ㎛의 직경 크기를 가질 수 있다. 상기 다공성 실리카의 오일 흡유량은 0.3 내지 3 cc/g 수준의 원료를 사용할 수 있다. 상기 다공성 실리카는 표면 개질된 레티노이드 담지 다공성 실리카 100 중량%에 대해 50 내지 99 중량%, 바람직하게는 60 내지 99 중량%, 더욱 바람직하게는 65 내지 94 중량%로 혼합될 수 있다. 상기 범위를 벗어날 경우 다공성 실리카 파우더가 균일한 가루 형태가 되지 않고 뭉친 형태로 제조될 수 있다. 이는 다른 화장품 제형에 분산시켰을 때 안정성에 영향을 끼칠 수 있다.The porous silica may have a diameter of 1 to 50 μm. The porous silica may use a raw material having an oil absorption of 0.3 to 3 cc/g. The porous silica may be mixed in an amount of 50 to 99 wt%, preferably 60 to 99 wt%, and more preferably 65 to 94 wt%, based on 100 wt% of the surface-modified retinoid-supported porous silica. If outside the above range, the porous silica powder may not be in the form of a uniform powder and may be manufactured in an agglomerated form. This may affect stability when dispersed in other cosmetic formulations.
제2단계는 표면 처리(개질)제로 실란계 화합물을 사용하여 폴리에톡실화된 레티노이드가 담지된 다공성 실리카의 표면을 개질하는 단계이다.The second step is a step of modifying the surface of the porous silica on which the polyethoxylated retinoid is supported by using a silane-based compound as a surface treatment (modification) agent.
제1단계에서 제조된 폴리에톡실화된 레티노이드가 담지된 다공성 실리카에 실란계 화합물을 투입하고 헨셀믹서를 이용하여 약 10분간 고르게 섞어준다. 다음으로, 표면 처리를 위해 40 내지 120 ℃에서 30분 내지 5시간, 더 구체적으로, 80 내지 100 ℃에서 1시간 내지 4시간 동안 반응시키는 열처리를 수행한 후 냉각시켜 표면 개질된 레티노이드 담지 다공성 실리카를 제조한다. 열처리가 상기 범위를 벗어나는 경우, 저온에서는 표면처리게 제대로 진행되지 않을수 있으며, 고온의 경우 레티노이드 변색 및 기타 물질의 안정성에 영향을 끼칠 수 있다.Introduce the silane-based compound to the porous silica supported with the polyethoxylated retinoid prepared in the first step, and mix evenly for about 10 minutes using a Henschel mixer. Next, for surface treatment, heat treatment is performed at 40 to 120 ° C. for 30 minutes to 5 hours, more specifically, at 80 to 100 ° C. for 1 hour to 4 hours, and then cooled to obtain a surface-modified retinoid-supported porous silica. manufacture If the heat treatment is out of the above range, surface treatment may not proceed properly at low temperatures, and discoloration of retinoid and stability of other materials may be affected in the case of high temperatures.
상기 실란계 화합물은 표면 개질된 레티노이드 담지 다공성 실리카 100 중량%에 대해 0.5 내지 20 중량%, 더 구체적으로 1 내지 15 중량%로 혼합될 수 있다. 상기 범위를 벗어날 경우 레티노이드 용출량이 감소하여 레티노이드의 효과가 감소되거나, 너무 과량일 경우 다공성 실리카 내부에 포집되지 못하고 실리카 표면에 존재할 수 있다. The silane-based compound may be mixed in an amount of 0.5 to 20 wt%, more specifically 1 to 15 wt%, based on 100 wt% of the surface-modified retinoid-supported porous silica. If the retinoid is out of the above range, the effect of the retinoid is reduced due to a decrease in the elution amount of the retinoid, or if the retinoid is too excessive, it may not be captured in the porous silica and may exist on the silica surface.
본 발명은 또한 상기의 표면 개질된 레티노이드 담지 다공성 실리카를 포함하는 화장료 조성물에 관한 것이다.The present invention also relates to a cosmetic composition comprising the surface-modified retinoid-supporting porous silica.
레티노이드는 피부내 섬유아세포의 증식 및 콜라겐 합성을 중식시키므로 본 발명의 화장료 조성물은 주름 기능성 화장품에 사용될 수 있다. Since retinoids neutralize the proliferation of fibroblasts and collagen synthesis in the skin, the cosmetic composition of the present invention can be used in wrinkle functional cosmetics.
또한, 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카는 O/W 제형에 파우더 형태로 사용될 수 있다. 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카는 화장료 조성물 100 중량%에 대해 0.01 내지 5 중량%, 더 구체적으로 0.05 내지 4 중량%로 포함될 수 있다. 상기 범위를 벗어나는 경우, 레티노이드의 효과가 미비하거나, 과량 사용으로 안정성 및 안전성에 영향을 끼칠 수 있다.In addition, the surface-modified retinoid-supported porous silica of the present invention can be used in an O/W formulation in powder form. The surface-modified retinoid-supported porous silica of the present invention may be included in an amount of 0.01 to 5% by weight, more specifically, 0.05 to 4% by weight, based on 100% by weight of the cosmetic composition. If it is out of the above range, the effect of the retinoid may be insignificant, or the stability and safety may be affected due to excessive use.
본 발명의 화장료 조성물은 일반적인 유화제형 또는 가용화 제형의 화장품 형태로 제조할 수 있다. 예컨대, 유연 화장수 또는 영양 화장수 등과 같은 화장수, 훼이셜 로션, 바디로션 등과 같은 유액, 영양 크림, 수분 크림, 아이 크림 등과 같은 크림, 에센스, 화장연고, 스프레이, 젤, 팩, 선 스크린, 메이크업 베이스, 액체 타입, 고체 타입 또는 스프레이 타입 등의 파운데이션, 파우더, 클렌징 크림, 클렌징 로션, 클렌징 오일과 같은 메이크업 제거제, 클렌징 폼, 비누, 바디 워쉬 등과 같은 세정제 등의 제형을 가질 수 있다. The cosmetic composition of the present invention may be prepared in the form of a general emulsifier or solubilization formulation. For example, lotion such as softening lotion or nourishing lotion, emulsion such as facial lotion, body lotion, etc., cream such as nourishing cream, moisture cream, eye cream, essence, cosmetic ointment, spray, gel, pack, sunscreen, makeup base, liquid It may have formulations such as foundation, powder, cleansing cream, cleansing lotion, makeup remover such as cleansing oil, cleanser such as cleansing foam, soap, body wash, and the like.
또한, 본 발명의 화장료 조성물은 일반적인 화장료 조성물의 제조 시 사용하는 보조 성분으로서 지방 물질, 유기 용매, 용해제, 농축제 및 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온봉쇄제 및 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭 또는 화장품에 통상적으로 사용되는 임의의 다른 성분과 같은 화장품학 분야에서 통상적으로 사용되는 보조제를 함유할 수 있다.In addition, the cosmetic composition of the present invention includes a fatty substance, an organic solvent, a solubilizing agent, a thickening agent and a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, Fragrance agents, surfactants, water, ionic or nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, blocking agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic actives, lipid vesicles or It may contain adjuvants commonly used in cosmetology, such as any other ingredients commonly used in cosmetics.
본 발명의 일 구체예에 따르면, 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카는 O/W 제형에 파우더 형태로 사용될 수 있으며, O/W 제형은 하기 표 2의 조성에 따라 75℃에서 유상 및 수상 성분을 완전히 용해시킨 이후, 호모믹서를 이용하여 1차 유화시키고, 본 발명의 표면 개질된 레티노이드 담지 다공성 실리카 파우더를 45℃에서 투입하여 2차 유화시켜 제조될 수 있다.According to one embodiment of the present invention, the surface-modified retinoid-supported porous silica of the present invention can be used in powder form in an O/W formulation, and the O/W formulation is an oil phase and an aqueous phase at 75° C. according to the composition of Table 2 below. After completely dissolving the ingredients, it can be prepared by primary emulsification using a homomixer, and secondary emulsification by introducing the surface-modified retinoid-supporting porous silica powder of the present invention at 45°C.
이하, 본 발명에 따르는 실시예 통하여 본 발명을 보다 상세히 설명하나, 본 발명의 범위가 하기 제시된 실시예에 의해 제한되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples according to the present invention, but the scope of the present invention is not limited by the examples presented below.
<실시예 1> 내지 <실시예 4> 표면 개질된 레티노이드 담지 다공성 실리카 파우더 제조 및 적용 제형<Example 1> to <Example 4> Preparation of surface-modified retinoid-supported porous silica powder and application formulation
표면 개질된 레티노이드 담지 다공성 실리카 제조를 위한 레티노이드는 폴리에톡실화 레틴아마이드를 사용하였다. 표 1의 조성과 같이 레티노이드 및 에탄올을 광 차단 조건에서 고르게 용해시킨 후, 헨셀믹서를 이용해서 다공성 실리카에 만들어진 레티노이드 용액을 서서히 투입하여 10분간 고르게 섞어주었다. 다공성 실리카의 크기는 1~50 ㎛의 직경을 사용하며, 다공성 실리카의 오일 흡유량은 0.3~3cc/g 수준의 원료를 사용하였다. 1차로 만들어진 파우더에 트리에톡시카프릴릴실란(triethoxycaprylylsilane)을 투입하여 헨셀믹서를 이용하여 10분간 고르게 섞어주었다. 표면 처리를 위해서 약 100℃에서 4시간 동안 반응시켜 표면 처리 반응을 실시한 후, 냉각하여 최종 표면 개질된 레티노이드 담지 다공성 실리카 파우더를 얻었다.Polyethoxylated retinamide was used as the retinoid for preparing the surface-modified retinoid-supported porous silica. As shown in Table 1, the retinoid and ethanol were evenly dissolved under light blocking conditions, and then the retinoid solution made in the porous silica was slowly added using a Henschel mixer and mixed evenly for 10 minutes. The porous silica used a diameter of 1 to 50 μm, and a raw material with an oil absorption of 0.3 to 3 cc/g was used. Triethoxycaprylylsilane was added to the powder made primarily and mixed evenly for 10 minutes using a Henschel mixer. For surface treatment, the surface treatment reaction was carried out by reacting at about 100 ° C. for 4 hours, and then cooled to obtain a final surface-modified retinoid-supported porous silica powder.
만들어진 레티노이드 담지 다공성 실리카 파우더를 실제 O/W 제형에 적용하였으며 조성은 표 2와 같다. 제조 방법은 75℃에서 유상 및 수상을 완전히 용해시킨 이후에, 호모믹서를 이용하여 1차 유화하여 제조하며 레티노이드 및 레티노이드 다공성 실리카 파우더는 45℃에서 투입 후, 2차 유화를 진행하였다.The prepared retinoid-supported porous silica powder was applied to the actual O/W formulation, and the composition is shown in Table 2. The manufacturing method is prepared by first emulsifying using a homomixer after completely dissolving the oil phase and the aqueous phase at 75 ° C. After introducing the retinoid and retinoid porous silica powder at 45 ° C, the second emulsification was performed.
(폴리에톡실화 레틴아마이드)retinoid
(Polyethoxylated Retinamide)
본 발명에서 사용된 레티노이드는 (주)엘에스켐에서 제조된 Medimin A(평균 분자량 831)를 이용하였으며, 다공성 실리카는 선진뷰티사이언스에서 제조된 sunsil-130, 표면처리제는 신에츠사의 AES 원료, 레티놀은 BASF사의 Retinol 50C를 사용하였다.The retinoid used in the present invention was Medimin A (average molecular weight 831) manufactured by LS Chem Co., Ltd., porous silica was sunsil-130 manufactured by Sunjin Beauty Science, surface treatment agent was Shin-Etsu's AES raw material, and retinol was BASF. Retinol 50C from the company was used.
<실험예 1> 레티놀/레티노이드 변색 비교 실험<Experimental Example 1> Retinol/Retinoid Discoloration Comparison Experiment
폴리에톡실화된 레티노이드가 담지된 다공성 실리카(실시예 3)에 실란계 화합물을 투입하고 헨셀믹서를 이용해서 고르게 분산시킨후 열처리 온도 조건에서 4시간 동안 반응시킨 후 얻어진 파우더는 아래와 같다. 비교예 3과 같이 레티놀의 경우 열처리 시에 변색이 일어난 반면, 실시예 3의 경우 열처리 온도가 100℃에서 연노란빛의 파우더가 얻어졌다. 반면에 130℃ 이상의 고온에서 열처리를 진행하는 경우 주황색의 파우더가 얻어진다.A silane-based compound was added to the porous silica (Example 3) loaded with polyethoxylated retinoid, dispersed evenly using a Henschel mixer, and then reacted for 4 hours under heat treatment temperature conditions. The obtained powder is as follows. As in Comparative Example 3, in the case of retinol, discoloration occurred during heat treatment, whereas in the case of Example 3, light yellow powder was obtained at a heat treatment temperature of 100 ° C. On the other hand, when heat treatment is performed at a high temperature of 130 ° C. or higher, orange powder is obtained.
<실험예 2> 레티노이드 안정성 개선 효과<Experimental Example 2> Retinoid stability improvement effect
레티노이드의 안정성을 확인하기 위해 순수 레티노이드(비교예 4), 레티노이드 담지 다공성 실리카 파우더 적용 제형(비교예 5), 표면 개질된 레티노이드 담지 다공성 실리카 파우더 적용 제형(실시예 4)에 대해서 경시별 역가분석을 실시하였다.In order to confirm the stability of the retinoid, a potency analysis over time was performed on the pure retinoid (Comparative Example 4), the retinoid-supporting porous silica powder-applied formulation (Comparative Example 5), and the surface-modified retinoid-supporting porous silica powder-applied formulation (Example 4). conducted.
표 4에 나타난 바와 같이, 비교예 4 < 비교예 5 = 실시예 4 순서로 안정성을 개선됨을 확인할 수 있었다. As shown in Table 4, it was confirmed that the stability was improved in the order of Comparative Example 4 < Comparative Example 5 = Example 4.
<실험예 3> 안전성 개선을 위한 서방형 약물전달체로서의 레티노이드 용출 거동 실험<Experimental Example 3> Retinoid dissolution behavior test as a sustained-release drug delivery system for safety improvement
(용매 조건별 레티노이드 용출 거동 실험)(Retinoid dissolution behavior test by solvent condition)
레티노이드의 방출 거동을 살펴 보기 위해 비교예 2 및 실시예 1~3을 화장품에서 흔히 사용하는 용매를 이용하여 1차적으로 용출 실험을 실시하였다. 용매로는 1,3-부틸렌 글리콜(1,3-butylene glycol)을 사용하였으며 비교예 2 및 실시예 1~3번 파우더를 용매에 5% 분산시킨 후 일주일 동안 진탕 배양기(shaking incubator)에서 일주일간 용출시켰다. 일주일 후, 용매의 상등액만을 분석하여 용출량을 계산하였다.In order to examine the release behavior of retinoid, comparative example 2 and examples 1 to 3 were primarily subjected to dissolution experiments using solvents commonly used in cosmetics. 1,3-butylene glycol was used as the solvent, and after dispersing 5% of the powders of Comparative Example 2 and Examples 1 to 3 in the solvent, the mixture was worked in a shaking incubator for a week. eluted for a week. After one week, only the supernatant of the solvent was analyzed to calculate the elution amount.
표 5에 나타난 바와 같이, 표면 처리가 안된 비교예 2의 경우 레티노이드가 모두 용출되었으며, 표면 처리된 실시예 1~3의 경우 서방형 약물전달체로 서서히 레티노이드를 용출시키는 것을 확인할 수 있었다. 또한, 트리에톡시카프릴릴실란의 농도 의존적(2~7%)으로 레티노이드의 용출량이 감소하였으며, 이를 통해 표면 개질된 레티노이드 다공성 실리카 파우더가 서방형 제제로서 응용 가능성이 있음을 확인하였다.As shown in Table 5, in the case of Comparative Example 2 where the surface was not treated, all retinoids were eluted, and in the case of Examples 1 to 3 where the surface was treated, it was confirmed that the retinoid was slowly eluted as a sustained-release drug delivery system. In addition, the amount of elution of retinoid decreased in a concentration-dependent manner (2-7%) of triethoxycaprylylsilane, and through this, it was confirmed that the surface-modified retinoid porous silica powder has applicability as a sustained-release formulation.
(O/W 제형에서의 레티노이드 방출 거동 실험)(Retinoid release behavior test in O/W formulation)
실제 화장품 제형에서의 레티노이드 용출 거동 및 피부 투과를 확인하기 위해 비교예 4의 제형과 용출량이 가장 낮은 실시예 3을 적용한 실시예 4 제형을 프란쯔 확산 셀(Franze diffusion cell) 실험을 통해 비교하였다. 피부 투과 장치는 아래 그림과 같은 장치를 사용하였으며 피부투과장치는 공여칸(donor chamber)과 수용칸(receptor chamber)으로 구성되어 있고 이 사이에 피부를 위치시킨 후 고정하였다(도 2 참조). 동일한 시험에 사용하는 각 셀은 2.54 cm2 의 동일한 표면적을 갖는다. 준비된 피부는 각질층(stratum corneum)이 위로 위치하도록 하여 피부투과장치에 고정한다. 수용칸의 수용액 양은 2.4 mL이며 시험물질의 확산에 영향을 주지 않게 300rpm 으로 교반하였다. 본 시험에서의 레티노이드의 농도는 196.85 ㎍/cm2 로 정하여 사용하였다. 피부 내 최대흡수율을 유지하기 위해 적용하는 제형의 양은 39.370 ㎕/cm2 로 하여 일정한 피부흡수상태를 유지하였으며, 피부 위에 고르게 도포 하였다. 시험 물질 도포 후, 6시간 / 24시간 실험이 종료된 시점에 피부를 채취하여 피부흡수율을 파악하였다.In order to confirm retinoid dissolution behavior and skin permeation in actual cosmetic formulations, the formulation of Comparative Example 4 and the formulation of Example 4 to which Example 3, which had the lowest dissolution amount, were compared through a Franze diffusion cell experiment. The skin penetration device used the device shown in the figure below, and the skin penetration device consisted of a donor chamber and a receptor chamber, and the skin was placed between them and then fixed (see FIG. 2). Each cell used for the same test has the same surface area of 2.54 cm 2 . The prepared skin is fixed to the skin penetrating device with the stratum corneum on top. The amount of aqueous solution in the receiving compartment was 2.4 mL and was stirred at 300 rpm so as not to affect the diffusion of the test substance. The concentration of retinoid in this test was set at 196.85 μg/cm 2 . The amount of the formulation applied to maintain the maximum absorption rate in the skin was 39.370 μl/cm 2 to maintain a constant skin absorption state, and was applied evenly on the skin. After the test substance was applied, the skin was collected at the end of the 6-hour / 24-hour experiment to determine the skin absorption rate.
표 6과 7 및 도 3과 4에서와 같이, 6시간 피부 흡수량을 비교하였을 때 비교예 4 대비 실시예 4는 서방형 약물전달체로 용출되는 레티노이드의 함량이 작지만, 24시간 피부 흡수량 비교 결과 다공성 실리카에 담지하지 않은 레티노이드와 동일량 흡수됨을 확인하였다. 따라서, 서방형 제제로 실시예 4가 레티노이드를 서서히 용출하지만 다공성 실리카에 담지하지 않은 레티노이드와 유사한 수준으로 흡수되며 동일한 효능/효과를 나타낼 수 있음을 확인할 수 있었다.As shown in Tables 6 and 7 and FIGS. 3 and 4, when the 6-hour skin absorption amount was compared, Example 4 compared to Comparative Example 4 had a small content of retinoid eluted as a sustained-release drug delivery system, but as a result of comparing the 24-hour skin absorption amount, porous silica It was confirmed that it was absorbed in the same amount as the retinoid not contained in the Accordingly, it was confirmed that Example 4, as a sustained-release formulation, slowly released the retinoid, but was absorbed at a similar level to the retinoid not loaded in the porous silica and exhibited the same efficacy/effect.
(㎍/cm2)skin absorption
(μg/cm 2 )
(24시간)Skin absorption rate (%)
(24 hours)
<실험예 4> 레티노이드 담지 다공성 실리카 파우더의 안전성 개선 효과<Experimental Example 4> Safety improvement effect of retinoid supported porous silica powder
(In vitro HET-CAM 테스트)( In vitro HET-CAM test)
유정란 안점막자극가능성평가를 통해서 안전성 개선 효과를 알아 보았다. 사용된 유정란의 종 및 계통은 백색 레그혼(white leghorn, white egg)이다. 유정란의 민감도를 점검하기 위해서 기준물질인 텍사폰(Texapon)을 이용하여 예비실험을 진행하여 출혈 및 용혈정도를 파악하며, 실험군과 비교하였다. 자극판단의 기준은 약한 자극성(slightly irritating), 중등도 자극성(moderately irritating), 자극성(irritating), 강한 자극성(severely irritating)으로 나눠서 평가 하였다. 표면 개질된 레티노이드 담지 다공성 실리카 파우더의 안전성을 확인하기 위해 비교예 1, 실시예 3 샘플을 HET-CAM 테스트를 진행하였다.The safety improvement effect was investigated through the evaluation of the possibility of irritation of the fertilized egg eye mucosa. The species and strain of fertilized eggs used are white leghorn (white egg). In order to check the sensitivity of fertilized eggs, a preliminary experiment was conducted using Texapon, a reference material, to determine the degree of bleeding and hemolysis, and compared with the experimental group. The criterion for judging stimulation was evaluated by dividing it into slightly irritating, moderately irritating, irritating, and severely irritating. In order to confirm the safety of the surface-modified retinoid-supported porous silica powder, the samples of Comparative Example 1 and Example 3 were subjected to the HET-CAM test.
표 8에 나타난 바와 같이, 다공성 실리카 담지 및 표면 개질된 실시예 3 샘플의 자극 지수가 비교예 1의 자극 지수대비 낮음을 확인하였다. As shown in Table 8, it was confirmed that the irritation index of the porous silica-supported and surface-modified sample of Example 3 was lower than that of Comparative Example 1.
(In vivo 소비자 품평 테스트)( In vivo consumer evaluation test)
표면 개질된 레티노이드 다공성 실리카 파우더의 안전성 개선 효과를 알아 보기 위해서 비교예 5와 실시예 4 샘플을 이용하여 소비자 자극 품평 테스트를 진행하였다. 품평은 여성 소비자 25명을 대상으로 저녁에 1회 사용하며 일주일간 사용한 후 최종 자극 품평을 진행하였다. 자극 품평의 척도는 5점 척도로 하였으며, 점수가 커질수록 자극의 강도가 세짐을 의미한다.In order to investigate the safety improvement effect of the surface-modified retinoid porous silica powder, a consumer stimulation evaluation test was conducted using samples of Comparative Example 5 and Example 4. For the evaluation, 25 female consumers used it once in the evening, and after using it for a week, the final stimulation evaluation was conducted. The scale of evaluation of the stimulus was on a 5-point scale, and the higher the score, the stronger the intensity of the stimulus.
도 5에 나타난 바와 같이, 비교예 5 및 실시예 4 둘 다 2점 이하로 자극이 약한 것으로 나타났다. As shown in FIG. 5, both Comparative Example 5 and Example 4 showed weak stimulation with 2 points or less.
Claims (15)
Retinoid-supported porous silica on which polyethoxylated retinoid is supported and whose surface is modified with a silane-based compound.
폴리에톡실화된 레티노이드는 폴리에톡실레이티드 레틴아마이드(polyethoxylated retinamide)를 포함하는, 레티노이드 담지 다공성 실리카.
According to claim 1,
A retinoid-supported porous silica, wherein the polyethoxylated retinoid includes polyethoxylated retinamide.
다공성 실리카는 1 내지 50 ㎛의 직경 크기를 갖는, 레티노이드 담지 다공성 실리카.
According to claim 1,
The porous silica having a diameter size of 1 to 50 μm, the retinoid-supported porous silica.
실란계 화합물은 트라이에톡시카프릴릴실레인(Triethoxycaprylylsilane), 아미노프로필트라이에톡시실레인(Aminopropyl Triethoxysilane), 글라이시독시프로필트라이메톡시실란(Glycidoxypropyl Trimethoxysilane), 아이소뷰틸트리에톡시실레인(Isobutyltriethoxysilane), 퍼플루오로옥틸에틸트라이에톡시실레인(Perfluorooctylethyl Triethoxysilane), 퍼플루오로옥틸트라이에톡시실레인(Perfluorooctyl Triethoxysilane), 스테아릴트라이에톡시실레인(Stearyl Triethoxysilane), 메틸트라이에톡시실레인(Methyltriethoxysilane), 피이지-8 메틸에터트라이에톡시실레인(PEG-8 Methyl Ether Triethoxysilane) 및 비닐에톡시실레인(Vinyltriethoxysilane)으로 이루어진 군에서 선택되는 하나 이상인, 레티노이드 담지 다공성 실리카.
According to claim 1,
Silane-based compounds include triethoxycaprylylsilane, aminopropyl triethoxysilane, glycidoxypropyl trimethoxysilane, and isobutyltriethoxysilane. ), Perfluorooctylethyl Triethoxysilane, Perfluorooctyl Triethoxysilane, Stearyl Triethoxysilane, Methyltriethoxysilane (Methyltriethoxysilane), PEG-8 Methyl Ether Triethoxysilane (PEG-8 Methyl Ether Triethoxysilane), and at least one selected from the group consisting of vinylethoxysilane (Vinyltriethoxysilane), retinoid-supported porous silica.
레티노이드 담지 다공성 실리카는 폴리에톡실화된 레티노이드 용액 및 다공성 실리카를 혼합하여 다공성 실리카 내에 폴리에톡실화된 레티노이드를 담지하고, 폴리에톡실화된 레티노이드가 담지된 다공성 실리카 및 실란계 화합물을 반응시켜 다공성 실리카의 표면을 개질하여 제조되는, 레티노이드 담지 다공성 실리카.
According to claim 1,
The retinoid-supported porous silica is formed by mixing a polyethoxylated retinoid solution and porous silica to support the polyethoxylated retinoid in the porous silica, and reacting the porous silica supported with the polyethoxylated retinoid with a silane-based compound to form porous silica. Retinoid-supported porous silica prepared by modifying the surface of silica.
폴리에톡실화된 레티노이드가 담지된 다공성 실리카 및 실란계 화합물을 반응시켜 다공성 실리카의 표면을 개질하는 단계를 포함하는 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
mixing the polyethoxylated retinoid solution and porous silica to support the polyethoxylated retinoid in the porous silica; and
A method for producing a surface-modified retinoid-supported porous silica comprising the step of modifying the surface of the porous silica by reacting the porous silica supported with polyethoxylated retinoid and a silane-based compound.
폴리에톡실화된 레티노이드는 폴리에톡실레이티드 레틴아마이드(polyethoxylated retinamide)를 포함하는, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
A method for producing surface-modified retinoid-supported porous silica, wherein the polyethoxylated retinoid includes polyethoxylated retinamide.
폴리에톡실화된 레티노이드 용액은 폴리에톡실화된 레티노이드를 광 차단 조건에서 용매에 녹여 제조하는, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
A method for producing a surface-modified retinoid-supported porous silica, wherein the polyethoxylated retinoid solution is prepared by dissolving the polyethoxylated retinoid in a solvent under light blocking conditions.
용매는 메탄올 또는 에탄올인, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 8,
Method for producing surface-modified retinoid-supported porous silica, wherein the solvent is methanol or ethanol.
폴리에톡실화된 레티노이드 용액은 하이드로카본계 오일, 에스터 오일, 천연오일, 실리콘 오일, 항산화제, 광안정성제, 항염제, 변색방지제, 자외선 차단제, 염료 및 안료로 이루어진 군에서 선택된 하나 이상을 더 포함하는, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
The polyethoxylated retinoid solution further contains at least one selected from the group consisting of hydrocarbon oils, ester oils, natural oils, silicone oils, antioxidants, light stabilizers, anti-inflammatory agents, anti-discoloration agents, sunscreens, dyes and pigments. Method for producing surface-modified retinoid-supported porous silica.
다공성 실리카는 1 내지 50 ㎛의 직경 크기를 갖는, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
A method for producing a surface-modified retinoid-supported porous silica, wherein the porous silica has a diameter of 1 to 50 μm.
폴리에톡실화된 레티노이드가 담지된 다공성 실리카 및 실란계 화합물의 반응은 40 내지 120℃에서 30분 내지 5시간 동안 수행되는, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
A method for producing a surface-modified retinoid-supported porous silica, wherein the reaction of the polyethoxylated retinoid-supported porous silica and the silane-based compound is performed at 40 to 120° C. for 30 minutes to 5 hours.
실란계 화합물은 트리에톡시카프릴릴실란(Triethoxycaprylylsilane), 아미노프로필트라이에톡시실레인(Aminopropyl Triethoxysilane), 글라이시독시프로필트라이메톡시실란(Glycidoxypropyl Trimethoxysilane), 아이소뷰틸트리에톡시실레인(Isobutyltriethoxysilane), 퍼플루오로옥틸에틸트라이에톡시실레인(Perfluorooctylethyl Triethoxysilane), 퍼플루오로옥틸트라이에톡시실레인(Perfluorooctyl Triethoxysilane), 스테아릴트라이에톡시실레인(Stearyl Triethoxysilane), 메틸트라이에톡시실레인(Methyltriethoxysilane), 피이지-8 메틸에터트라이에톡시실레인(PEG-8 Methyl Ether Triethoxysilane) 및 비닐에톡시실레인(Vinyltriethoxysilane)으로 이루어진 군에서 선택되는 하나 이상인, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
Silane compounds include Triethoxycaprylylsilane, Aminopropyl Triethoxysilane, Glycidoxypropyl Trimethoxysilane, Isobutyltriethoxysilane , Perfluorooctylethyl Triethoxysilane, Perfluorooctyl Triethoxysilane, Stearyl Triethoxysilane, Methyltriethoxysilane ( Methyltriethoxysilane), PEG-8 Methyl Ether Triethoxysilane (PEG-8 Methyl Ether Triethoxysilane), and at least one selected from the group consisting of vinylethoxysilane (Vinyltriethoxysilane), Preparation of surface-modified retinoid-supported porous silica method.
실란계 화합물은 표면 개질된 레티노이드 담지 다공성 실리카 100 중량%에 대해 0.5 내지 20 중량%로 혼합되는, 표면 개질된 레티노이드 담지 다공성 실리카의 제조방법.
According to claim 6,
A method for preparing a surface-modified retinoid-supported porous silica, wherein the silane-based compound is mixed in an amount of 0.5 to 20% by weight based on 100% by weight of the surface-modified retinoid-supported porous silica.
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| CN202210710367.7A CN115531230A (en) | 2021-06-29 | 2022-06-22 | Surface modified retinoid-loaded porous silica |
| TW111123770A TW202317065A (en) | 2021-06-29 | 2022-06-24 | Surface modified retinoid immersion porous silica |
| PCT/KR2022/009120 WO2023277479A1 (en) | 2021-06-29 | 2022-06-27 | Surface-modified retinoid-impregnated porous silica |
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| KR20230001874A true KR20230001874A (en) | 2023-01-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020210084952A KR20230001874A (en) | 2021-06-29 | 2021-06-29 | Surface modified retinoid immersion porous silica |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR20230001874A (en) |
| CN (1) | CN115531230A (en) |
| TW (1) | TW202317065A (en) |
| WO (1) | WO2023277479A1 (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101314100B1 (en) | 2011-07-12 | 2013-10-04 | (주)에이씨티 | Stabilizing method of an unstable retinol using nanoparticles of silica coated lipid monolayer shell and biodegradable polymer core and cosmetic composition containing the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2451534A2 (en) * | 2009-06-19 | 2012-05-16 | U.S. Cosmetics Corporation | Cosmetic compositions and methods for enhanced uv protection |
| KR101346792B1 (en) * | 2010-09-03 | 2014-01-02 | 주식회사 엘지생활건강 | Cosmetic composition for improving skin wrinkle comprising polyethoxylated retinamide in nanoliposome comprising UV absorber |
| KR20210028109A (en) * | 2019-08-28 | 2021-03-11 | 주식회사 비제이바이오켐 | Cosmetic composition comprising silica ceramide composite |
-
2021
- 2021-06-29 KR KR1020210084952A patent/KR20230001874A/en not_active Application Discontinuation
-
2022
- 2022-06-22 CN CN202210710367.7A patent/CN115531230A/en active Pending
- 2022-06-24 TW TW111123770A patent/TW202317065A/en unknown
- 2022-06-27 WO PCT/KR2022/009120 patent/WO2023277479A1/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101314100B1 (en) | 2011-07-12 | 2013-10-04 | (주)에이씨티 | Stabilizing method of an unstable retinol using nanoparticles of silica coated lipid monolayer shell and biodegradable polymer core and cosmetic composition containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023277479A1 (en) | 2023-01-05 |
| CN115531230A (en) | 2022-12-30 |
| TW202317065A (en) | 2023-05-01 |
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