KR20230056879A - Biodegradable microcapsules and manufacturing method of the same - Google Patents
Biodegradable microcapsules and manufacturing method of the same Download PDFInfo
- Publication number
- KR20230056879A KR20230056879A KR1020210140663A KR20210140663A KR20230056879A KR 20230056879 A KR20230056879 A KR 20230056879A KR 1020210140663 A KR1020210140663 A KR 1020210140663A KR 20210140663 A KR20210140663 A KR 20210140663A KR 20230056879 A KR20230056879 A KR 20230056879A
- Authority
- KR
- South Korea
- Prior art keywords
- biodegradable
- diisocyanate
- based material
- cyclohexane
- capsule
- Prior art date
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- 239000003094 microcapsule Substances 0.000 title claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 169
- 239000002775 capsule Substances 0.000 claims abstract description 82
- -1 aliphatic isocyanate Chemical class 0.000 claims abstract description 71
- 239000011162 core material Substances 0.000 claims abstract description 69
- 239000012948 isocyanate Substances 0.000 claims abstract description 47
- 239000000178 monomer Substances 0.000 claims abstract description 45
- 150000002632 lipids Chemical class 0.000 claims abstract description 40
- 229920002988 biodegradable polymer Polymers 0.000 claims abstract description 10
- 239000004621 biodegradable polymer Substances 0.000 claims abstract description 10
- 239000003921 oil Substances 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 66
- 229930186217 Glycolipid Natural products 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 42
- 150000003904 phospholipids Chemical class 0.000 claims description 41
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 claims description 36
- 239000012782 phase change material Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 229940088594 vitamin Drugs 0.000 claims description 26
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- JSPNNZKWADNWHI-PNANGNLXSA-N (2r)-2-hydroxy-n-[(2s,3r,4e,8e)-3-hydroxy-9-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]heptadecanamide Chemical compound CCCCCCCCCCCCCCC[C@@H](O)C(=O)N[C@H]([C@H](O)\C=C\CC\C=C(/C)CCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JSPNNZKWADNWHI-PNANGNLXSA-N 0.000 claims description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 24
- 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 24
- 229930183167 cerebroside Natural products 0.000 claims description 24
- RIZIAUKTHDLMQX-UHFFFAOYSA-N cerebroside D Natural products CCCCCCCCCCCCCCCCC(O)C(=O)NC(C(O)C=CCCC=C(C)CCCCCCCCC)COC1OC(CO)C(O)C(O)C1O RIZIAUKTHDLMQX-UHFFFAOYSA-N 0.000 claims description 24
- 239000000796 flavoring agent Substances 0.000 claims description 22
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- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- 239000000839 emulsion Substances 0.000 claims description 19
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 19
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 18
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 17
- 230000001681 protective effect Effects 0.000 claims description 17
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 claims description 16
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 claims description 16
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- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 16
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- 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 12
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- 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 12
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/20—After-treatment of capsule walls, e.g. hardening
- B01J13/206—Hardening; drying
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
Description
본 발명은 생분해성 캡슐 및 그 제조방법에 관한 것으로, 더욱 상세하게는 자연에서 분해되어 환경을 오염시키지 않고, 인체에 유해한 성분이 잔류하지 않아 피부 등의 인체에 무해하며, 생분해성의 캡슐벽 내부에 심물질이 포집되어 안정화된 상태를 이루는 생분해성 마이크로캡슐 및 그 제조방법에 관한 것이다.The present invention relates to a biodegradable capsule and a manufacturing method thereof, and more particularly, to a biodegradable capsule wall that is degradable in nature and does not pollute the environment, and is harmless to the human body such as the skin because there is no residual component harmful to the human body. It relates to biodegradable microcapsules in which core substances are collected and stabilized, and a manufacturing method thereof.
최근 전세계적 이슈가 되고 있는 미세플라스틱의 환경오염은 해양 생태계를 파괴하고, 더 나아가 인간의 식탁에까지 영향을 미치는 상황에 이르렀다. 이에 국제기구 및 각국은 미세플라스틱의 생산 및 판매에 제동을 걸기 시작했으며, 대체 물질을 찾지 않으면 여러 산업분야에 사용되는 기능성 화학소재에 입자 형태의 물질을 활용하여 기능성을 부여하기가 어려워지고 있다.The environmental pollution of microplastics, which has recently become a global issue, has reached a situation where it destroys the marine ecosystem and further affects the human table. Accordingly, international organizations and countries have begun to put a brake on the production and sale of microplastics, and unless alternative materials are found, it is becoming difficult to impart functionality by using particle-type materials to functional chemical materials used in various industries.
또한, 국내에서는 살생물제 등의 부작용을 겪으면서 각종 산업소재, 자재 부품에 적용되는 화학소재의 안전성을 강화하고 있다.In addition, in Korea, the safety of chemical materials applied to various industrial materials and materials parts is being strengthened while experiencing side effects such as biocides.
기존 마이크로캡슐들은 대부분 플라스틱 소재로 되어 있으며, 포름알데히드, 유기용매 등과 같은 유해 물질이 포함되어 있다.Existing microcapsules are mostly made of plastic materials and contain harmful substances such as formaldehyde and organic solvents.
한편, 지금까지 생분해성 물질과 관련된 개발 분야는 생분해성 수지나 약물전달시스템 등에 집중되어 있고, 입자의 형태는 천연물을 이용하여 다층코팅이나 이온겔화반응 등을 통해 리포솜, 비드, 에멀젼 형태로 만들어지고 있다. 생분해가 가능한 물질로 생분해 마이크로캡슐을 제조하는 경우에는 드롭핑(Dropping), 마이크로-플뤼드 시스템(Micro-Fluid System), 다층코팅의 방법 등으로 만들어지는데, 이와 같은 방법으로는 마이크로캡슐의 벽재 성분의 제한, 제조방법 상의 한계 등으로 인해 마이크로캡슐의 생산성이나 안정성을 확보하기 어렵다.On the other hand, development fields related to biodegradable materials have been concentrated on biodegradable resins or drug delivery systems so far, and the shape of particles is made in the form of liposomes, beads, and emulsions through multi-layer coating or ion gelation reaction using natural materials. there is. In the case of manufacturing biodegradable microcapsules with biodegradable materials, they are made by methods such as dropping, micro-fluid system, and multi-layer coating. These methods include wall components of microcapsules. It is difficult to secure the productivity or stability of microcapsules due to limitations in manufacturing methods and limitations of manufacturing methods.
따라서, 환경을 오염시키지 않으면서 인체에 해가 되지 않고, 기존 생분해 캡슐보다 성능이 향상된 새로운 개념의 캡슐 개발이 요구되고 있다.Therefore, there is a demand for the development of a new concept capsule that does not pollute the environment, does not harm the human body, and has improved performance compared to existing biodegradable capsules.
본 발명이 해결하고자 하는 과제는 자연에서 분해되어 환경을 오염시키지 않고, 인체에 유해한 성분이 잔류하지 않아 피부 등의 인체에 무해하며, 생분해성의 캡슐벽 내부에 심물질이 포집되어 안정화된 상태를 이루는 생분해성 마이크로캡슐 및 그 제조방법을 제공함에 있다. The problem to be solved by the present invention is that it is decomposed in nature, does not pollute the environment, does not remain harmful to the human body, is harmless to the human body such as the skin, and core substances are collected inside the biodegradable capsule wall to achieve a stable state. It is to provide a biodegradable microcapsule and a manufacturing method thereof.
본 발명은, 캡슐벽이 심물질의 유상을 둘러싸고 있는 형태를 갖는 캡슐로서, 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽을 이루고, 상기 캡슐은 0.1∼300㎛의 크기를 갖는 생분해성 마이크로캡슐을 제공한다. The present invention is a capsule having a shape in which the capsule wall surrounds the oil phase of the core material, and a biodegradable polymer formed by reacting a biodegradable lipid-based material with an aliphatic isocyanate monomer constitutes the capsule wall of the capsule, and the capsule has a 0.1 Biodegradable microcapsules with a size of -300 μm are provided.
상기 생분해성 지질계 물질은 스핑고 지질계 물질, 당지질계 물질, 스핑고 당지질계 물질 및 인지질계 물질로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The biodegradable lipid-based material may include at least one material selected from the group consisting of sphingo lipid-based materials, glycolipid-based materials, sphingo-glycolipid-based materials, and phospholipid-based materials.
상기 스핑고 지질계 물질은 세라미드, 피토세라미드, 스핑고미엘린, 세레브로시드, 갱글리오시드 또는 이들의 혼합물을 포함할 수 있다.The sphingolipid-based material may include ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물을 포함할 수 있다.The glycolipid-based material may include glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof.
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물을 포함할 수 있다.The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, It may include sulfatide (sulfated galactocerebroside), ganglioside, globoside, or mixtures thereof.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin) 또는 이들의 혼합물을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin or Mixtures of these may be included.
상기 지방족계 이소시아네이트 단량체는 4,4'-디시클로헥실메탄 디이소시아네이트(4,4'-Dicyclohexylmethane diisocyanate), 트랜스-1,4-시클로헥산 디이소시아네이트(trans-1,4-Cyclohexane diisocyanate), 이소포론 디이소시아네이트(Isophorone diisocyanate), 헥사메틸렌 디이소시아네이트(Hexamethylene diisocyanate), 트리메틸 헥사메틸렌 디이소시아네이트(Trimethyl hexamethylene diisocyanate), 1,3-비스(이소시아노메틸)시클로헥산(1,3-Bis(Isocyanomethyl) cyclohexane), 2.4-디이소시아네이토시클로헥산(2.4-diisocyanato cyclohexane), 1,6-디이소시아네이토-2,2,4-트리메틸헥산(1,6-diisocyanato-2,2,4-trimethylhexane), 1, 6-디이소시아네이토-2,4,4-트리메틸헥산(1,6-diisocyanato-2,4,4-trimethylhexane), 1-이소시아네이토메틸-3-이소시아네이토-l,5,5-트리메틸시클로헥산(1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), 테트라메톡시부탄 1,4- 디이소시아네이트(tetramethoxybutane 1,4- diisocyanate), 부탄 1,4-디이소시아네이트(butane 1,4-diisocyanate), 헥산 1,6- 디이소시아네이트(hexane 1,6- diisocyanate), 디시클로헥실메탄 디이소시아네이트(dicyclohexylmethane diisocyanate) 및 시클로헥산 1,4-디이소시아네이트(cyclohexane 1,4-diisocyanate)로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate, isophorone Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-Bis(Isocyanomethyl)cyclohexane ), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-isocyanato-l, 5,5-trimethylcyclohexane (1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), tetramethoxybutane 1,4- diisocyanate, butane 1,4- Butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4-diisocyanate 4-diisocyanate) may include one or more materials selected from the group consisting of.
상기 심물질은 노나데칸, 옥타데칸, 헵타데칸, 헥사데칸, 테트라데칸, 펜타데칸스테아린산, 시안 아미드, 프로필 아미드 및 펜타에리츠리톨 로 이루어진 군으로부터 선택된 1종 이상의 상변화물질을 포함할 수 있다.The core material may include at least one phase change material selected from the group consisting of nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecane stearic acid, cyanamide, propyl amide, and pentaerythritol.
상기 심물질은 α-카로틴, β-카로틴, 레티놀, 트레티노인, 알파칼시돌, 다이하이드로타키스테롤, 칼시포트리올, 토코페롤, 나프토퀴논 및 필로퀴논으로 이루어진 군으로부터 선택된 1종 이상의 지용성 비타민을 포함할 수 있다.The heart substance includes at least one fat-soluble vitamin selected from the group consisting of α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotakisterol, calcipotriol, tocopherol, naphthoquinone, and phylloquinone. can do.
상기 심물질은 상변화물질(PCM; phase change material), 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물을 포함할 수 있다.The core material may include a phase change material (PCM), a fat-soluble vitamin, a functional fragrance, a functional oil, or a mixture thereof.
또한, 본 발명은, 캡슐벽이 심물질의 유상을 둘러싸고 있는 형태를 갖는 캡슐을 제조하는 방법으로서, 심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체를 혼합하는 단계와, 심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체의 혼합물에 상기 심물질을 유화시킬 수 있는 인지질계 물질 수용액을 혼합하고 유화시켜 유상/수상 에멀젼이 형성되게 하는 단계와, 상기 유상/수상 에멀젼에 열을 가하여 교반하면서 반응시켜 캡슐이 형성되게 하는 단계 및 상기 반응 결과물에 보호콜로이드 화합물을 혼합하는 단계를 포함하며, 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽을 이루고, 상기 캡슐은 0.1∼300㎛의 크기를 갖는 생분해성 마이크로캡슐의 제조방법을 제공한다. In addition, the present invention is a method for manufacturing a capsule having a shape in which the capsule wall surrounds the oil phase of the core material, comprising the steps of mixing the core material, a biodegradable lipid-based material and an aliphatic isocyanate monomer, Mixing and emulsifying an aqueous solution of a phospholipid-based material capable of emulsifying the core material with a mixture of a lipid-based material and an aliphatic-based isocyanate monomer to form an oil/aqueous phase emulsion, while stirring by applying heat to the oil/water phase emulsion Reacting to form a capsule and mixing a protective colloid compound with the reaction product, wherein the biodegradable polymer formed by reacting the biodegradable lipid-based material with the aliphatic isocyanate monomer forms the capsule wall of the capsule, The capsule provides a method for producing biodegradable microcapsules having a size of 0.1 to 300 μm.
상기 생분해성 지질계 물질은 스핑고 지질계 물질, 당지질계 물질, 스핑고 당지질계 물질 및 인지질계 물질로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The biodegradable lipid-based material may include at least one material selected from the group consisting of sphingo lipid-based materials, glycolipid-based materials, sphingo-glycolipid-based materials, and phospholipid-based materials.
상기 스핑고 지질계 물질은 세라미드, 피토세라미드, 스핑고미엘린, 세레브로시드, 갱글리오시드 또는 이들의 혼합물을 포함할 수 있다.The sphingolipid-based material may include ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물을 포함할 수 있다.The glycolipid-based material may include glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof.
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드, 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물을 포함할 수 있다.The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactoserebroside, glucose cerebroside, sulfatide ( sulfatide or sulfurized galactocerebroside), ganglioside, globoside, or mixtures thereof.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin) 또는 이들의 혼합물을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin or Mixtures of these may be included.
상기 지방족계 이소시아네이트 단량체는 4,4'-디시클로헥실메탄 디이소시아네이트(4,4'-Dicyclohexylmethane diisocyanate), 트랜스-1,4-시클로헥산 디이소시아네이트(trans-1,4-Cyclohexane diisocyanate), 이소포론 디이소시아네이트(Isophorone diisocyanate), 헥사메틸렌 디이소시아네이트(Hexamethylene diisocyanate), 트리메틸 헥사메틸렌 디이소시아네이트(Trimethyl hexamethylene diisocyanate), 1,3-비스(이소시아노메틸)시클로헥산(1,3-Bis(Isocyanomethyl) cyclohexane), 2.4-디이소시아네이토시클로헥산(2.4-diisocyanato cyclohexane), 1,6-디이소시아네이토-2,2,4-트리메틸헥산(1,6-diisocyanato-2,2,4-trimethylhexane), 1, 6-디이소시아네이토-2,4,4-트리메틸헥산(1,6-diisocyanato-2,4,4-trimethylhexane), 1-이소시아네이토메틸-3-이소시아네이토-l,5,5-트리메틸시클로헥산(1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), 테트라메톡시부탄 1,4- 디이소시아네이트(tetramethoxybutane 1,4- diisocyanate), 부탄 1,4-디이소시아네이트(butane 1,4-diisocyanate), 헥산 1,6- 디이소시아네이트(hexane 1,6- diisocyanate), 디시클로헥실메탄 디이소시아네이트(dicyclohexylmethane diisocyanate) 및 시클로헥산 1,4-디이소시아네이트(cyclohexane 1,4-diisocyanate)로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate, isophorone Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-Bis(Isocyanomethyl)cyclohexane ), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-isocyanato-l, 5,5-trimethylcyclohexane (1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), tetramethoxybutane 1,4- diisocyanate, butane 1,4- Butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4-diisocyanate 4-diisocyanate) may include one or more materials selected from the group consisting of.
상기 생분해성 지질계 물질은 심물질 100중량부에 대하여 1∼20중량부를 혼합하는 것이 바람직하다.The biodegradable lipid-based material is preferably mixed in an amount of 1 to 20 parts by weight based on 100 parts by weight of the core material.
상기 지방족계 이소시아네이트 단량체는 심물질 100중량부에 대하여 0.1∼10중량부를 혼합하는 것이 바람직하다.It is preferable to mix 0.1 to 10 parts by weight of the aliphatic isocyanate monomer based on 100 parts by weight of the core material.
상기 인지질계 물질 수용액은 심물질 100중량부에 대하여 인지질계 물질을 1∼10중량부 혼합하고 심물질 100중량부에 대하여 물을 10∼90중량부를 투입하여 만든 수용액일 수 있다.The aqueous solution of the phospholipid-based material may be an aqueous solution prepared by mixing 1 to 10 parts by weight of the phospholipid-based material with respect to 100 parts by weight of the core material and adding 10 to 90 parts by weight of water with respect to 100 parts by weight of the core material.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin) 및 세팔린(Cephalin)으로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin and cephalin. It may include one or more materials selected from the group consisting of.
상기 보호콜로이드 화합물은 상기 지방족계 이소시아네이트 단량체와 반응 가능한 하이드록시기 또는 아민기를 가진 물질을 포함할 수 있다.The protective colloidal compound may include a material having a hydroxy group or an amine group capable of reacting with the aliphatic isocyanate monomer.
상기 심물질은 노나데칸, 옥타데칸, 헵타데칸, 헥사데칸, 테트라데칸, 펜타데칸스테아린산, 시안 아미드, 프로필 아미드 및 펜타에리츠리톨 로 이루어진 군으로부터 선택된 1종 이상의 상변화물질을 포함할 수 있다.The core material may include at least one phase change material selected from the group consisting of nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecane stearic acid, cyanamide, propyl amide, and pentaerythritol.
상기 심물질은 α-카로틴, β-카로틴, 레티놀, 트레티노인, 알파칼시돌, 다이하이드로타키스테롤, 칼시포트리올, 토코페롤, 나프토퀴논 및 필로퀴논으로 이루어진 군으로부터 선택된 1종 이상의 지용성 비타민을 포함할 수 있다.The heart substance includes at least one fat-soluble vitamin selected from the group consisting of α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotakisterol, calcipotriol, tocopherol, naphthoquinone, and phylloquinone. can do.
상기 심물질은 상변화물질(PCM; phase change material), 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물을 포함할 수 있다.The core material may include a phase change material (PCM), a fat-soluble vitamin, a functional fragrance, a functional oil, or a mixture thereof.
본 발명에 의하면, 자연에서 분해되어 환경을 오염시키지 않고, 인체에 유해한 성분이 잔류하지 않아 피부 등의 인체에 무해하며, 생분해성의 캡슐벽 내부에 심물질이 포집되어 안정화된 상태를 이룬다. According to the present invention, it is decomposed in nature and does not pollute the environment, and no components harmful to the human body remain, so it is harmless to the human body such as the skin, and the core material is collected inside the biodegradable capsule wall to form a stable state.
본 발명에 의하면, 공기 중에서 쉽게 휘발되거나 산화로 인하여 변질될 수 있는 불안정한 향료나 기능성 오일을 캡슐화하여 안정화시킴으로써 불안정한 향료나 기능성 오일을 화학 생활용품, 화장품 제형 등에 적용함에 있어서 발생하던 불안정성 문제를 개선할 수 있으며, 제품의 효능도 오래 지속할 수 있다. According to the present invention, by encapsulating and stabilizing unstable fragrances or functional oils that can be easily volatilized in air or deteriorated due to oxidation, it is possible to improve the instability problem that occurs when applying unstable fragrances or functional oils to chemical household products, cosmetic formulations, etc. and the effectiveness of the product can last for a long time.
생분해성의 캡슐벽을 갖는 생분해성 마이크로캡슐은 그 내부에 심물질이 포집되어 안정화 된다. 이러한 생분해성 마이크로캡슐은 건축·토목용 자재, 액체세제, 섬유유연제 등과 같은 화학제품의 소재 뿐만 아니라, 액체제형의 샴푸, 바디소프 등 퍼스널케어 등의 액체제형의 화장품 소재로도 폭넓게 적용할 수 있다.A biodegradable microcapsule having a biodegradable capsule wall is stabilized by collecting core material therein. These biodegradable microcapsules can be widely applied not only as materials for chemical products such as building and civil engineering materials, liquid detergents, and fabric softeners, but also as liquid-type cosmetic materials such as liquid-type shampoo and body soap for personal care. .
도 1은 본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐을 도시한 도면이다.1 is a view showing a biodegradable microcapsule according to a preferred embodiment of the present invention.
이하, 첨부된 도면을 참조하여 본 발명에 따른 바람직한 실시예를 상세하게 설명한다. 그러나, 이하의 실시예는 이 기술분야에서 통상적인 지식을 가진 자에게 본 발명이 충분히 이해되도록 제공되는 것으로서 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 다음에 기술되는 실시예에 한정되는 것은 아니다. Hereinafter, preferred embodiments according to the present invention will be described in detail with reference to the accompanying drawings. However, the following embodiments are provided to those skilled in the art to sufficiently understand the present invention, and may be modified in various forms, and the scope of the present invention is limited to the following examples. it is not going to be
발명의 상세한 설명 또는 청구범위에서 어느 하나의 구성요소가 다른 구성요소를 "포함"한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 당해 구성요소만으로 이루어지는 것으로 한정되어 해석되지 아니하며, 다른 구성요소를 더 포함할 수 있는 것으로 이해되어야 한다.When it is said that any one component "includes" another component in the detailed description or claims of the invention, it is not construed as being limited to only the corresponding component unless otherwise stated, and other components are not further defined. It should be understood that it can include.
본 발명은 사용 후 자연에서 분해되어 환경을 오염시키지 않고, 인체에 유해한 성분이 잔류하지 않아 피부 등의 인체에 무해하며, 기존의 생분해 캡슐과 비교하여 물리화학적 성질, 경제성 및 활용성이 향상된 생분해성 마이크로캡슐 및 그 제조방법을 제시한다.The present invention is degraded in nature after use and does not pollute the environment, does not remain harmful to the human body, is harmless to the human body such as the skin, and has improved physicochemical properties, economic feasibility and usability compared to existing biodegradable capsules. Microcapsules and their manufacturing method are presented.
본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐은, 캡슐벽이 심물질의 유상을 둘러싸고 있는 형태를 갖는 캡슐로서, 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽을 이루고, 상기 캡슐은 0.1∼300㎛의 크기를 가질 수 있다. The biodegradable microcapsule according to a preferred embodiment of the present invention is a capsule having a shape in which the capsule wall surrounds the oil phase of the core material, and the biodegradable polymer formed by reacting the biodegradable lipid-based material with the aliphatic isocyanate monomer is the capsule. forming a capsule wall, and the capsule may have a size of 0.1 to 300 μm.
상기 생분해성 지질계 물질은 스핑고 지질계 물질, 당지질계 물질, 스핑고 당지질계 물질 및 인지질계 물질로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The biodegradable lipid-based material may include at least one material selected from the group consisting of sphingo lipid-based materials, glycolipid-based materials, sphingo-glycolipid-based materials, and phospholipid-based materials.
상기 스핑고 지질계 물질은 세라미드, 피토세라미드, 스핑고미엘린, 세레브로시드, 갱글리오시드 또는 이들의 혼합물을 포함할 수 있다.The sphingolipid-based material may include ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물을 포함할 수 있다.The glycolipid-based material may include glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof.
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물을 포함할 수 있다.The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, It may include sulfatide (sulfated galactocerebroside), ganglioside, globoside, or mixtures thereof.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin) 또는 이들의 혼합물을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin or Mixtures of these may be included.
상기 지방족계 이소시아네이트 단량체는 4,4'-디시클로헥실메탄 디이소시아네이트(4,4'-Dicyclohexylmethane diisocyanate), 트랜스-1,4-시클로헥산 디이소시아네이트(trans-1,4-Cyclohexane diisocyanate), 이소포론 디이소시아네이트(Isophorone diisocyanate), 헥사메틸렌 디이소시아네이트(Hexamethylene diisocyanate), 트리메틸 헥사메틸렌 디이소시아네이트(Trimethyl hexamethylene diisocyanate), 1,3-비스(이소시아노메틸)시클로헥산(1,3-Bis(Isocyanomethyl) cyclohexane), 2.4-디이소시아네이토시클로헥산(2.4-diisocyanato cyclohexane), 1,6-디이소시아네이토-2,2,4-트리메틸헥산(1,6-diisocyanato-2,2,4-trimethylhexane), 1, 6-디이소시아네이토-2,4,4-트리메틸헥산(1,6-diisocyanato-2,4,4-trimethylhexane), 1-이소시아네이토메틸-3-이소시아네이토-l,5,5-트리메틸시클로헥산(1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), 테트라메톡시부탄 1,4- 디이소시아네이트(tetramethoxybutane 1,4- diisocyanate), 부탄 1,4-디이소시아네이트(butane 1,4-diisocyanate), 헥산 1,6- 디이소시아네이트(hexane 1,6- diisocyanate), 디시클로헥실메탄 디이소시아네이트(dicyclohexylmethane diisocyanate) 및 시클로헥산 1,4-디이소시아네이트(cyclohexane 1,4-diisocyanate)로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate, isophorone Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-Bis(Isocyanomethyl)cyclohexane ), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-isocyanato-l, 5,5-trimethylcyclohexane (1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), tetramethoxybutane 1,4- diisocyanate, butane 1,4- Butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4-diisocyanate 4-diisocyanate) may include one or more materials selected from the group consisting of.
상기 심물질은 노나데칸, 옥타데칸, 헵타데칸, 헥사데칸, 테트라데칸, 펜타데칸스테아린산, 시안 아미드, 프로필 아미드 및 펜타에리츠리톨 로 이루어진 군으로부터 선택된 1종 이상의 상변화물질을 포함할 수 있다.The core material may include at least one phase change material selected from the group consisting of nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecane stearic acid, cyanamide, propyl amide, and pentaerythritol.
상기 심물질은 α-카로틴, β-카로틴, 레티놀, 트레티노인, 알파칼시돌, 다이하이드로타키스테롤, 칼시포트리올, 토코페롤, 나프토퀴논 및 필로퀴논으로 이루어진 군으로부터 선택된 1종 이상의 지용성 비타민을 포함할 수 있다.The heart substance includes at least one fat-soluble vitamin selected from the group consisting of α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotakisterol, calcipotriol, tocopherol, naphthoquinone, and phylloquinone. can do.
상기 심물질은 상변화물질(PCM; phase change material), 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물을 포함할 수 있다.The core material may include a phase change material (PCM), a fat-soluble vitamin, a functional fragrance, a functional oil, or a mixture thereof.
본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐의 제조방법은, 캡슐벽이 심물질의 유상을 둘러싸고 있는 형태를 갖는 캡슐을 제조하는 방법으로서, 심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체를 혼합하는 단계와, 심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체의 혼합물에 상기 심물질을 유화시킬 수 있는 인지질계 물질 수용액을 혼합하고 유화시켜 유상/수상 에멀젼이 형성되게 하는 단계와, 상기 유상/수상 에멀젼에 열을 가하여 교반하면서 반응시켜 캡슐이 형성되게 하는 단계 및 상기 반응 결과물에 보호콜로이드 화합물을 혼합하는 단계를 포함하며, 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽을 이루고, 상기 캡슐은 0.1∼300㎛의 크기를 가질 수 있다. A method for manufacturing biodegradable microcapsules according to a preferred embodiment of the present invention is a method for manufacturing a capsule having a shape in which the capsule wall surrounds the oil phase of the core substance, the core substance, the biodegradable lipid-based substance and the aliphatic isocyanate monomer. Mixing and emulsifying an aqueous solution of a phospholipid-based material capable of emulsifying the core material with a mixture of a core material, a biodegradable lipid-based material, and an aliphatic isocyanate monomer to form an oil/water phase emulsion; Biodegradation formed by reacting a biodegradable lipid-based material with an aliphatic isocyanate monomer, comprising a step of reacting with stirring while applying heat to the oil/aqueous emulsion to form a capsule and mixing a protective colloid compound with the reaction product A sex polymer forms the capsule wall of the capsule, and the capsule may have a size of 0.1 to 300 μm.
상기 생분해성 지질계 물질은 스핑고 지질계 물질, 당지질계 물질, 스핑고 당지질계 물질 및 인지질계 물질로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The biodegradable lipid-based material may include at least one material selected from the group consisting of sphingo lipid-based materials, glycolipid-based materials, sphingo-glycolipid-based materials, and phospholipid-based materials.
상기 스핑고 지질계 물질은 세라미드, 피토세라미드, 스핑고미엘린, 세레브로시드, 갱글리오시드 또는 이들의 혼합물을 포함할 수 있다.The sphingolipid-based material may include ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물을 포함할 수 있다.The glycolipid-based material may include glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof.
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물을 포함할 수 있다.The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, It may include sulfatide (sulfated galactocerebroside), ganglioside, globoside, or mixtures thereof.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin) 또는 이들의 혼합물을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin or Mixtures of these may be included.
상기 지방족계 이소시아네이트 단량체는 4,4'-디시클로헥실메탄 디이소시아네이트(4,4'-Dicyclohexylmethane diisocyanate), 트랜스-1,4-시클로헥산 디이소시아네이트(trans-1,4-Cyclohexane diisocyanate), 이소포론 디이소시아네이트(Isophorone diisocyanate), 헥사메틸렌 디이소시아네이트(Hexamethylene diisocyanate), 트리메틸 헥사메틸렌 디이소시아네이트(Trimethyl hexamethylene diisocyanate), 1,3-비스(이소시아노메틸)시클로헥산(1,3-Bis(Isocyanomethyl) cyclohexane), 2.4-디이소시아네이토시클로헥산(2.4-diisocyanato cyclohexane), 1,6-디이소시아네이토-2,2,4-트리메틸헥산(1,6-diisocyanato-2,2,4-trimethylhexane), 1, 6-디이소시아네이토-2,4,4-트리메틸헥산(1,6-diisocyanato-2,4,4-trimethylhexane), 1-이소시아네이토메틸-3-이소시아네이토-l,5,5-트리메틸시클로헥산(1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), 테트라메톡시부탄 1,4- 디이소시아네이트(tetramethoxybutane 1,4- diisocyanate), 부탄 1,4-디이소시아네이트(butane 1,4-diisocyanate), 헥산 1,6- 디이소시아네이트(hexane 1,6- diisocyanate), 디시클로헥실메탄 디이소시아네이트(dicyclohexylmethane diisocyanate) 및 시클로헥산 1,4-디이소시아네이트(cyclohexane 1,4-diisocyanate)로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate, isophorone Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-Bis(Isocyanomethyl)cyclohexane ), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-isocyanato-l, 5,5-trimethylcyclohexane (1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), tetramethoxybutane 1,4- diisocyanate, butane 1,4- Butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4-diisocyanate 4-diisocyanate) may include one or more materials selected from the group consisting of.
상기 생분해성 지질계 물질은 심물질 100중량부에 대하여 1∼20중량부를 혼합하는 것이 바람직하다.The biodegradable lipid-based material is preferably mixed in an amount of 1 to 20 parts by weight based on 100 parts by weight of the core material.
상기 지방족계 이소시아네이트 단량체는 심물질 100중량부에 대하여 0.1∼10중량부를 혼합하는 것이 바람직하다.It is preferable to mix 0.1 to 10 parts by weight of the aliphatic isocyanate monomer based on 100 parts by weight of the core material.
상기 인지질계 물질 수용액은 심물질 100중량부에 대하여 인지질계 물질을 1∼10중량부 혼합하고 심물질 100중량부에 대하여 물을 10∼90중량부를 투입하여 만든 수용액일 수 있다.The aqueous solution of the phospholipid-based material may be an aqueous solution prepared by mixing 1 to 10 parts by weight of the phospholipid-based material with respect to 100 parts by weight of the core material and adding 10 to 90 parts by weight of water with respect to 100 parts by weight of the core material.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin) 및 세팔린(Cephalin)으로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin and cephalin. It may include one or more materials selected from the group consisting of.
상기 보호콜로이드 화합물은 상기 지방족계 이소시아네이트 단량체와 반응 가능한 하이드록시기 또는 아민기를 가진 물질을 포함할 수 있다.The protective colloidal compound may include a material having a hydroxy group or an amine group capable of reacting with the aliphatic isocyanate monomer.
상기 심물질은 노나데칸, 옥타데칸, 헵타데칸, 헥사데칸, 테트라데칸, 펜타데칸스테아린산, 시안 아미드, 프로필 아미드 및 펜타에리츠리톨 로 이루어진 군으로부터 선택된 1종 이상의 상변화물질을 포함할 수 있다.The core material may include at least one phase change material selected from the group consisting of nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecane stearic acid, cyanamide, propyl amide, and pentaerythritol.
상기 심물질은 α-카로틴, β-카로틴, 레티놀, 트레티노인, 알파칼시돌, 다이하이드로타키스테롤, 칼시포트리올, 토코페롤, 나프토퀴논 및 필로퀴논으로 이루어진 군으로부터 선택된 1종 이상의 지용성 비타민을 포함할 수 있다.The heart substance includes at least one fat-soluble vitamin selected from the group consisting of α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotakisterol, calcipotriol, tocopherol, naphthoquinone, and phylloquinone. can do.
상기 심물질은 상변화물질(PCM; phase change material), 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물을 포함할 수 있다.The core material may include a phase change material (PCM), a fat-soluble vitamin, a functional fragrance, a functional oil, or a mixture thereof.
이하에서, 본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐을 더욱 구체적으로 설명한다. Hereinafter, the biodegradable microcapsules according to a preferred embodiment of the present invention will be described in more detail.
도 1은 본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐을 도시한 도면이다.1 is a view showing a biodegradable microcapsule according to a preferred embodiment of the present invention.
도 1을 참조하면, 본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐은, 캡슐벽(10)이 심물질의 유상(20)을 둘러싸고 있는 형태를 갖는 캡슐로서, 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽(10)을 이루고, 상기 캡슐은 0.1∼300㎛의 직경을 갖는다. Referring to FIG. 1, the biodegradable microcapsule according to a preferred embodiment of the present invention is a capsule having a shape in which the
상기 심물질은 상변화물질(PCM; phase change material), 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물을 포함할 수 있다. The core material may include a phase change material (PCM), a fat-soluble vitamin, a functional fragrance, a functional oil, or a mixture thereof.
상기 생분해성 마이크로캡슐은 상변화물질, 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들의 혼합물이 캡슐벽 내부에 심물질로서 포집되어 있는 형태를 이루고 있다. The biodegradable microcapsules form a form in which phase change materials, fat-soluble vitamins, functional flavors, functional oils, or mixtures thereof are trapped inside the capsule walls as core substances.
상기 상변화물질은 노나데칸, 옥타데칸, 헵타데칸, 헥사데칸, 테트라데칸, 펜타데칸스테아린산, 시안 아미드, 프로필 아미드, 펜타에리츠리톨 또는 이들의 혼합물 등과 같이 건축용이나 토목용 기능성 소재로 쓰여지는 물질일 수 있다. The phase change material is a material used as a functional material for construction or civil engineering, such as nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecane stearic acid, cyanamide, propyl amide, pentaerythritol or mixtures thereof can be
상기 지용성 비타민은 α-카로틴, β-카로틴, 레티놀, 트레티노인, 알파칼시돌, 다이하이드로타키스테롤, 칼시포트리올, 토코페롤, 나프토퀴논, 필로퀴논 또는 이들의 혼합물 등일 수 있다. The fat-soluble vitamin may be α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotakisterol, calcipotriol, tocopherol, naphthoquinone, phylloquinone, or mixtures thereof.
상기 기능성 향료는 아로마허브향료, 장미향료, 자스민향료, 라벤더향료, 민트향료, 바나나향료, 사과향료, 딸기향료, 바닐라향료 또는 이들의 혼합물 등일 수 있다.The functional flavor may be aroma herb flavor, rose flavor, jasmine flavor, lavender flavor, mint flavor, banana flavor, apple flavor, strawberry flavor, vanilla flavor, or a mixture thereof.
상기 기능성 오일은 천연오일, 합성오일, 유성오일 또는 이들의 혼합물일 수 있다. 상기 천연오일은 파라핀/스쿠알란 등의 탄화수소계 오일, 호호바오일, 올리브오일, 허브오일, 메도폼씨드오일, 로즈힙오일, 카놀라오일, 동백오일, 아르간오일, 아보카도오일, 코코넛오일, 아몬드오일, 마카다미아오일, 티트리오일, 유칼립투스오일, 로즈마리오일, 라벤더오일 또는 이들의 혼합물 등일 수 있다. 상기 합성오일은 에스테르계 오일, 디메치콘, 메칠폴리실록산 등의 실리콘계 오일 또는 이들의 혼합물 등일 수 있다. 상기 유성오일은 레티놀, 세라마이드, 에칠헥실살리실레이트, 에칠헥실메톡시신나메이트, 알파-비사보롤, 유용성감초추출물, 토코페롤, 레티놀 등의 비타민계 오일, 아데노신, 알부틴, 카르노신, 페닐에틸레조시놀, 에틸헥실트리아존, 에틸헥실메톡시신나메이트, 에틸헥실살리실레이트, 옥토크릴렌, 이소아밀-p-메톡시신나메이트, 디에틸헥실 2,6-나프탈레이트, 에틸헥실이소노나노에이트 또는 이들의 혼합물 등과 같이 화장품, 퍼스널케어 용품 등의 생활용품 원료로 쓰여지는 물질일 수 있다. 아데노신, 알부틴, 카르노신, 페닐에틸레조시놀 등은 주름개선, 미백개선 물질로 화장품 원료로 사용되고, 에틸헥실트리아존, 에틸헥실메톡시신나메이트, 에틸헥실살리실레이트, 옥토크릴렌, 이소아밀-p-메톡시신나메이트 등은 자외선 차단제의 원료로 사용되며, 디에틸헥실 2,6-나프탈레이트, 에틸헥실이소노나노에이트 등은 피부유연화 용도의 기능성 오일로 화장품 원료로 사용된다. The functional oil may be natural oil, synthetic oil, oily oil, or a mixture thereof. The natural oils include hydrocarbon oils such as paraffin/squalane, jojoba oil, olive oil, herb oil, meadowfoam seed oil, rosehip oil, canola oil, camellia oil, argan oil, avocado oil, coconut oil, almond oil, and macadamia oil. , tea tree oil, eucalyptus oil, rosemary oil, lavender oil, or mixtures thereof. The synthetic oil may be a silicone-based oil such as ester-based oil, dimethicone, or methylpolysiloxane, or a mixture thereof. The oily oil is retinol, ceramide, ethylhexyl salicylate, ethylhexyl methoxycinnamate, alpha-bisabolol, oil-soluble licorice extract, tocopherol, vitamin-based oils such as retinol, adenosine, arbutin, carnosine, phenylethylreso Cynol, ethylhexyltriazone, ethylhexylmethoxycinnamate, ethylhexyl salicylate, octocrylene, isoamyl-p-methoxycinnamate, diethylhexyl 2,6-naphthalate, ethylhexylisononano It may be a material used as a raw material for household items such as cosmetics, personal care products, etc., such as eight or a mixture thereof. Adenosine, arbutin, carnosine, phenylethylresorcinol, etc. are used as cosmetic raw materials for wrinkle improvement and whitening improvement substances, and ethylhexyltriazone, ethylhexylmethoxycinnamate, ethylhexyl salicylate, octocrylene, isoamyl -p-Methoxycinnamate is used as a raw material for sunscreens, and diethylhexyl 2,6-naphthalate and ethylhexyl isononanoate are functional oils for skin softening and are used as raw materials for cosmetics.
상기 생분해성 폴리머는 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성되고 상기 캡슐의 캡슐벽(10)을 이루고 있다. 후술하는 바와 같이, 제조 과정에서 유화를 위해 첨가하는 인지질계 물질 수용액에 함유된 인지질계 물질의 일부도 지방족계 이소시아네이트 단량체와 반응하여 캡슐의 캡슐벽(10)을 이룰 수 있다. The biodegradable polymer is formed by reacting a biodegradable lipid-based material with an aliphatic isocyanate monomer and forms the
상기 생분해성 지질계 물질은 스핑고 지질계 물질, 당지질계 물질, 스핑고 당지질계 물질 및 인지질계 물질로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The biodegradable lipid-based material may include at least one material selected from the group consisting of sphingo lipid-based materials, glycolipid-based materials, sphingo-glycolipid-based materials, and phospholipid-based materials.
상기 스핑고 지질계 물질은 세라미드, 피토세라미드, 스핑고미엘린, 세레브로시드, 갱글리오시드 또는 이들의 혼합물 등을 포함할 수 있다. The sphingolipid-based material may include ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물 등을 포함할 수 있다. The glycolipid-based material may include glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof.
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물 등을 포함할 수 있다. The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, It may include sulfatide (sulfatide or sulfurized galactocerebroside), ganglioside, globoside, or mixtures thereof.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(PE; phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin), 이들의 혼합물 등을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine (PE), phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin ), mixtures thereof, and the like.
상기 지방족계 이소시아네이트 단량체는 4,4'-디시클로헥실메탄 디이소시아네이트(4,4'-Dicyclohexylmethane diisocyanate), 트랜스-1,4-시클로헥산 디이소시아네이트(trans-1,4-Cyclohexane diisocyanate), 이소포론 디이소시아네이트(Isophorone diisocyanate), 헥사메틸렌 디이소시아네이트(Hexamethylene diisocyanate), 트리메틸 헥사메틸렌 디이소시아네이트(Trimethyl hexamethylene diisocyanate), 1,3-비스(이소시아노메틸)시클로헥산(1,3-Bis(Isocyanomethyl) cyclohexane), 2.4-디이소시아네이토시클로헥산(2.4-diisocyanato cyclohexane), 1,6-디이소시아네이토-2,2,4-트리메틸헥산(1,6-diisocyanato-2,2,4-trimethylhexane), 1, 6-디이소시아네이토-2,4,4-트리메틸헥산(1,6-diisocyanato-2,4,4-trimethylhexane), 1-이소시아네이토메틸-3-이소시아네이토-l,5,5-트리메틸시클로헥산(1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), 테트라메톡시부탄 1,4- 디이소시아네이트(tetramethoxybutane 1,4- diisocyanate), 부탄 1,4-디이소시아네이트(butane 1,4-diisocyanate), 헥산 1,6- 디이소시아네이트(hexane 1,6- diisocyanate), 디시클로헥실메탄 디이소시아네이트(dicyclohexylmethane diisocyanate) 및 시클로헥산 1,4-디이소시아네이트(cyclohexane 1,4-diisocyanate)로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate, isophorone Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-Bis(Isocyanomethyl)cyclohexane ), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-isocyanato-l, 5,5-trimethylcyclohexane (1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), tetramethoxybutane 1,4- diisocyanate, butane 1,4- Butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4-diisocyanate 4-diisocyanate) may include one or more materials selected from the group consisting of.
캡슐벽(10)을 형성하는 상기 생분해성 폴리머는 심물질의 유상(20)(상변화물질, 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들의 혼합물의 유상) 100중량부에 대하여 2∼80중량부, 더욱 바람직하게는 5∼50중량부를 이루고 있는 것이 바람직하다. 생분해성 폴리머를 상기 범위보다 적게 사용한 경우 심물질의 유상(20)을 포집하여 캡슐을 형성하기 어려운 문제점이 있을 수 있고, 지나치게 많이 사용한 경우에는 입자의 크기가 너무 커져서 뭉침 현상이 발생할 수 있다. The biodegradable polymer forming the
이하에서, 본 발명의 바람직한 실시예에 따른 생분해성 마이크로캡슐의 제조방법을 더욱 구체적으로 설명한다. Hereinafter, a method for preparing biodegradable microcapsules according to a preferred embodiment of the present invention will be described in more detail.
심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체를 혼합한다. 이에 대하여 더욱 구체적으로 설명한다.A core material, a biodegradable lipid-based material, and an aliphatic isocyanate monomer are mixed. This will be described in more detail.
심물질과 생분해성 지질계 물질을 혼합한다. 상기 생분해성 지질계 물질은 심물질 100중량부에 대하여 1∼20중량부를 혼합하는 것이 바람직하다.Mix the core material and the biodegradable lipid-based material. The biodegradable lipid-based material is preferably mixed in an amount of 1 to 20 parts by weight based on 100 parts by weight of the core material.
상기 심물질은 상변화물질(PCM; phase change material), 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물을 포함할 수 있다. The core material may include a phase change material (PCM), a fat-soluble vitamin, a functional fragrance, a functional oil, or a mixture thereof.
상기 상변화물질은 노나데칸, 옥타데칸, 헵타데칸, 헥사데칸, 테트라데칸, 펜타데칸스테아린산, 시안 아미드, 프로필 아미드, 펜타에리츠리톨 또는 이들의 혼합물 등과 같이 건축용이나 토목용 기능성 소재로 쓰여지는 물질일 수 있다. The phase change material is a material used as a functional material for construction or civil engineering, such as nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecane stearic acid, cyanamide, propyl amide, pentaerythritol or mixtures thereof can be
상기 지용성 비타민은 α-카로틴, β-카로틴, 레티놀, 트레티노인, 알파칼시돌, 다이하이드로타키스테롤, 칼시포트리올, 토코페롤, 나프토퀴논, 필로퀴논 또는 이들의 혼합물 등일 수 있다. The fat-soluble vitamin may be α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotakisterol, calcipotriol, tocopherol, naphthoquinone, phylloquinone, or mixtures thereof.
상기 기능성 향료는 아로마허브향료, 장미향료, 자스민향료, 라벤더향료, 민트향료, 바나나향료, 사과향료, 딸기향료, 바닐라향료 또는 이들의 혼합물 등일 수 있다.The functional flavor may be aroma herb flavor, rose flavor, jasmine flavor, lavender flavor, mint flavor, banana flavor, apple flavor, strawberry flavor, vanilla flavor, or a mixture thereof.
상기 기능성 오일은 천연오일, 합성오일, 유성오일 또는 이들의 혼합물일 수 있다. 상기 천연오일은 파라핀/스쿠알란 등의 탄화수소계 오일, 호호바오일, 올리브오일, 허브오일, 메도폼씨드오일, 로즈힙오일, 카놀라오일, 동백오일, 아르간오일, 아보카도오일, 코코넛오일, 아몬드오일, 마카다미아오일, 티트리오일, 유칼립투스오일, 로즈마리오일, 라벤더오일 또는 이들의 혼합물 등일 수 있다. 상기 합성오일은 에스테르계 오일, 디메치콘, 메칠폴리실록산 등의 실리콘계 오일 또는 이들의 혼합물 등일 수 있다. 상기 유성오일은 레티놀, 세라마이드, 에칠헥실살리실레이트, 에칠헥실메톡시신나메이트, 알파-비사보롤, 유용성감초추출물, 토코페롤, 레티놀 등의 비타민계 오일, 아데노신, 알부틴, 카르노신, 페닐에틸레조시놀, 에틸헥실트리아존, 에틸헥실메톡시신나메이트, 에틸헥실살리실레이트, 옥토크릴렌, 이소아밀-p-메톡시신나메이트, 디에틸헥실 2,6-나프탈레이트, 에틸헥실이소노나노에이트 또는 이들의 혼합물 등과 같이 화장품, 퍼스널케어 용품 등의 생활용품 원료로 쓰여지는 물질일 수 있다. 아데노신, 알부틴, 카르노신, 페닐에틸레조시놀 등은 주름개선, 미백개선 물질로 화장품 원료로 사용되고, 에틸헥실트리아존, 에틸헥실메톡시신나메이트, 에틸헥실살리실레이트, 옥토크릴렌, 이소아밀-p-메톡시신나메이트 등은 자외선 차단제의 원료로 사용되며, 디에틸헥실 2,6-나프탈레이트, 에틸헥실이소노나노에이트 등은 피부유연화 용도의 기능성 오일로 화장품 원료로 사용된다. The functional oil may be natural oil, synthetic oil, oily oil, or a mixture thereof. The natural oils include hydrocarbon oils such as paraffin/squalane, jojoba oil, olive oil, herb oil, meadowfoam seed oil, rosehip oil, canola oil, camellia oil, argan oil, avocado oil, coconut oil, almond oil, and macadamia oil. , tea tree oil, eucalyptus oil, rosemary oil, lavender oil, or mixtures thereof. The synthetic oil may be a silicone-based oil such as ester-based oil, dimethicone, or methylpolysiloxane, or a mixture thereof. The oily oil is retinol, ceramide, ethylhexyl salicylate, ethylhexyl methoxycinnamate, alpha-bisabolol, oil-soluble licorice extract, tocopherol, vitamin-based oils such as retinol, adenosine, arbutin, carnosine, phenylethylreso Cynol, ethylhexyltriazone, ethylhexylmethoxycinnamate, ethylhexyl salicylate, octocrylene, isoamyl-p-methoxycinnamate, diethylhexyl 2,6-naphthalate, ethylhexylisononano It may be a material used as a raw material for household items such as cosmetics, personal care products, etc., such as eight or a mixture thereof. Adenosine, arbutin, carnosine, phenylethylresorcinol, etc. are used as cosmetic raw materials for wrinkle improvement and whitening improvement substances, and ethylhexyltriazone, ethylhexylmethoxycinnamate, ethylhexyl salicylate, octocrylene, isoamyl -p-Methoxycinnamate is used as a raw material for sunscreens, and diethylhexyl 2,6-naphthalate and ethylhexyl isononanoate are functional oils for skin softening and are used as raw materials for cosmetics.
상기 심물질은 건축·토목 등의 기능성 소재(상변화물질), 화장품, 퍼스널케어 용품, 생활용품 등에서 요구되는 기능성 향료, 기능성 오일, 지용성 비타민 등으로서 캡슐화가 필요하다면 상기에 열거된 물질에 국한되는 것은 아니다. The core material is a functional material (phase change material) such as construction and civil engineering, functional fragrance, functional oil, fat-soluble vitamin, etc. required for cosmetics, personal care products, household goods, etc. If encapsulation is required, it is limited to the materials listed above It is not.
상기 생분해성 지질계 물질은 스핑고 지질계 물질, 당지질계 물질, 스핑고 당지질계 물질 및 인지질계 물질로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The biodegradable lipid-based material may include at least one material selected from the group consisting of sphingo lipid-based materials, glycolipid-based materials, sphingo-glycolipid-based materials, and phospholipid-based materials.
상기 스핑고 지질계 물질은 세라미드, 피토세라미드, 스핑고미엘린, 세레브로시드, 갱글리오시드 또는 이들의 혼합물 등일 수 있다. The sphingolipid-based material may be ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물 등일 수 있다. The glycolipid-based material may be a glycerol glycolipid, a galatolipid, a sulfolipid, or a mixture thereof.
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물 등일 수 있다. The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, It may be sulfatide (sulfatide or sulfurized galactocerebroside), ganglioside, globoside, or mixtures thereof.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(PE; phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin) 및 세팔린(Cephalin)으로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine (PE), phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin and cephalin. ) may include one or more materials selected from the group consisting of.
심물질과 생분해성 지질계 물질의 혼합물에 지방족계 이소시아네이트 단량체를 혼합한다. 상기 지방족계 이소시아네이트 단량체는 심물질 100중량부에 대하여 0.1∼10중량부를 혼합하는 것이 바람직하다.An aliphatic isocyanate monomer is mixed with a mixture of a core material and a biodegradable lipid-based material. It is preferable to mix 0.1 to 10 parts by weight of the aliphatic isocyanate monomer based on 100 parts by weight of the core material.
상기 지방족계 이소시아네이트 단량체는 4,4'-디시클로헥실메탄 디이소시아네이트(4,4'-Dicyclohexylmethane diisocyanate), 트랜스-1,4-시클로헥산 디이소시아네이트(trans-1,4-Cyclohexane diisocyanate), 이소포론 디이소시아네이트(Isophorone diisocyanate), 헥사메틸렌 디이소시아네이트(Hexamethylene diisocyanate), 트리메틸 헥사메틸렌 디이소시아네이트(Trimethyl hexamethylene diisocyanate), 1,3-비스(이소시아노메틸)시클로헥산(1,3-Bis(Isocyanomethyl) cyclohexane), 2.4-디이소시아네이토시클로헥산(2.4-diisocyanato cyclohexane), 1,6-디이소시아네이토-2,2,4-트리메틸헥산(1,6-diisocyanato-2,2,4-trimethylhexane), 1, 6-디이소시아네이토-2,4,4-트리메틸헥산(1,6-diisocyanato-2,4,4-trimethylhexane), 1-이소시아네이토메틸-3-이소시아네이토-l,5,5-트리메틸시클로헥산(1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), 테트라메톡시부탄 1,4- 디이소시아네이트(tetramethoxybutane 1,4- diisocyanate), 부탄 1,4-디이소시아네이트(butane 1,4-diisocyanate), 헥산 1,6- 디이소시아네이트(hexane 1,6- diisocyanate), 디시클로헥실메탄 디이소시아네이트(dicyclohexylmethane diisocyanate) 및 시클로헥산 1,4-디이소시아네이트(cyclohexane 1,4-diisocyanate) 로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다.The aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate, isophorone Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-Bis(Isocyanomethyl)cyclohexane ), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-isocyanato-l, 5,5-trimethylcyclohexane (1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane), tetramethoxybutane 1,4- diisocyanate, butane 1,4- Butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4-diisocyanate 4-diisocyanate) may include one or more materials selected from the group consisting of.
심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체의 혼합물에 인지질계 물질 수용액을 혼합하고 유화시켜 유상/수상 에멀젼이 형성되게 한다. 심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체를 혼합한 후, 심물질을 유화시킬 수 있는 인지질계 물질 수용액을 혼합하고 교반하게 되면 유화가 일어난다. 상기 유화에 의해 유상/수상(Oil/Water, O/W 또는 Oil in Water) 에멀젼(유화 에멀젼)이 형성되게 된다. 상기 유상/수상 에멀젼을 형성하는 유화 공정 단계에서 그 교반 속도 및 교반 시간을 조절하여 캡슐 입자 크기를 조절할 수 있다. 생분해성 마이크로캡슐을 제조함에 있어서, 캡슐 입자 크기를 조절하기 위해서는 교반 속도, 교반 시간 등을 조절한다. 상기 교반은 호모믹서 등을 이용할 수 있으며, 교반 속도는 500∼5,000rpm 정도인 것이 바람직하고, 교반 시간은 1분∼1시간, 더욱 바람직하게는 1∼30분 정도인 것이 바람직하다. 교반 시간이 지나치게 짧으면 캡슐 크기가 커져서 생분해성 마이크로캡슐을 건축재료, 화학제품 등과 혼합시 분산 안정성이 나빠져서 침전이 발생할 수 있고, 캡슐의 효능이 저하될 수 있다. 교반을 지나치게 오랫동안 많이 하면 캡슐의 크기가 지나치게 작아져 캡슐 내에 심물질의 포집이 어려워질 수 있으며, 포집율이 저하될 수 있다. 교반 속도, 교반 시간 등을 조절하여 생분해성 마이크로캡슐의 크기를 조절할 수 있으며, 심물질인 상변화물질, 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물의 안정도를 높여 주어, 생분해성 마이크로캡슐을 건축재료, 화학제품 등에 혼합시 분산성 및 안정성을 높여줄 수가 있다. 교반 속도를 높이고 교반 시간을 길게 해주면 작은 입자가 형성되어 심물질(상변화물질, 지용성 비타민, 기능성 향료, 기능성 오일 또는 이들 혼합물)의 안정도를 더 높일 수 있다. An aqueous solution of a phospholipid-based material is mixed with a mixture of a core material, a biodegradable lipid-based material, and an aliphatic isocyanate monomer, and then emulsified to form an oil/water phase emulsion. After mixing the core material, the biodegradable lipid-based material, and the aliphatic isocyanate monomer, emulsification occurs when an aqueous solution of the phospholipid-based material capable of emulsifying the core material is mixed and stirred. By the emulsification, an oil/water phase (Oil/Water, O/W or Oil in Water) emulsion (emulsion emulsion) is formed. In the emulsification process step of forming the oil/aqueous emulsion, the size of the capsule particles may be adjusted by adjusting the stirring speed and stirring time. In preparing biodegradable microcapsules, stirring speed, stirring time, etc. are adjusted in order to control the size of the capsule particles. For the stirring, a homomixer or the like may be used, and the stirring speed is preferably about 500 to 5,000 rpm, and the stirring time is about 1 minute to 1 hour, more preferably about 1 to 30 minutes. If the stirring time is too short, the size of the capsules increases, and when the biodegradable microcapsules are mixed with building materials, chemicals, etc., dispersion stability may be deteriorated, and precipitation may occur, and the effectiveness of the capsules may be reduced. If the agitation is carried out for an excessively long time, the size of the capsule becomes too small, making it difficult to collect the core material in the capsule, and the collection rate may decrease. The size of biodegradable microcapsules can be controlled by adjusting the stirring speed and stirring time, and the stability of core substances such as phase change substances, fat-soluble vitamins, functional flavors, functional oils, or mixtures thereof is increased to build biodegradable microcapsules. Dispersibility and stability can be improved when mixing materials and chemicals. If the stirring speed is increased and the stirring time is increased, small particles are formed and the stability of the core material (phase change material, fat-soluble vitamin, functional flavor, functional oil, or a mixture thereof) can be further increased.
심물질을 유화시킬 수 있는 인지질계 물질 수용액은 심물질 100중량부에 대하여 인지질계 물질을 1∼10중량부 혼합하고 심물질 100중량부에 대하여 물을 10∼90중량부를 투입하여 만든 수용액일 수 있다. 상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(PE; phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin) 및 세팔린(Cephalin)으로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함할 수 있다. An aqueous solution of a phospholipid-based material capable of emulsifying a core material may be an aqueous solution made by mixing 1 to 10 parts by weight of a phospholipid-based material with respect to 100 parts by weight of the core material and adding 10 to 90 parts by weight of water with respect to 100 parts by weight of the core material. there is. The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine (PE), phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin and cephalin. ) may include one or more materials selected from the group consisting of.
상기 유상/수상 에멀젼에 열을 가하여 교반하면서 반응시켜 캡슐이 형성되게 한다. 상기 유상/수상 에멀젼을 교반하면서 반응시키게 되면 생분해성 마이크로캡슐이 형성되게 된다. 상기 반응은 40∼90℃, 더욱 바람직하게는 50∼80℃, 가장 바람직하게는 60∼80℃의 온도에서 수행하는 것이 바람직하다. 상기 교반은 100∼1000rpm 정도의 속도로 수행하는 것이 바람직하다. 상기 유상/수상 에멀젼을 반응시키게 되면 시간이 지남에 따라 경화되어 캡슐벽이 형성되고, 최종적으로는 생분해 마이크로캡슐이 형성되게 된다. 상기 생분해성 마이크로캡슐은 생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 캡슐의 캡슐벽을 이루며, 인지질계 물질 수용액에 함유된 인지질계 물질의 일부도 지방족계 이소시아네이트 단량체와 반응하여 캡슐의 캡슐벽을 이룰 수 있다. 사용하는 생분해성 지질계 물질, 사용하는 인지질계 물질 수용액, 사용하는 지방족계 이소시아네이트 단량체, 이들의 배합비 등에 따라서 캡슐벽의 강도를 조절할 수 있다. Heat is applied to the oil/aqueous emulsion to react while stirring to form capsules. When the oil/aqueous emulsion is reacted while stirring, biodegradable microcapsules are formed. The reaction is preferably carried out at a temperature of 40 to 90°C, more preferably 50 to 80°C, and most preferably 60 to 80°C. The stirring is preferably performed at a speed of about 100 to 1000 rpm. When the oil/aqueous emulsion is reacted, it hardens over time to form a capsule wall, and finally biodegradable microcapsules are formed. In the biodegradable microcapsule, a biodegradable lipid-based material reacts with an aliphatic isocyanate monomer to form a capsule wall, and a portion of the phospholipid-based material contained in an aqueous phospholipid-based material reacts with the aliphatic isocyanate monomer to form a capsule wall of the capsule. can achieve The strength of the capsule wall can be adjusted according to the biodegradable lipid-based material used, the aqueous solution of the phospholipid-based material used, the aliphatic isocyanate monomer used, and the mixing ratio thereof.
상기 반응 결과물에 보호콜로이드 화합물을 혼합한다. 상기 보호콜로이드 화합물은 상기 지방족계 이소시아네이트와 반응 가능한 하이드록시기 또는 아민기를 가진 물질을 포함한다. 이러한 상기 보호콜로이드 화합물의 예로는 피이지-20소르비탄모노라우레이트, 피이지-20소르비탄모노팔미테이트, 피이지-20소르비탄스테아레이트, 피이지-20소르비탄모노올레이트, 피이지-40하이드로제네이티드캐스터오일, 피이지-50하이드로제네이티드캐스터오일, 피이지-60하이드로제네이티드캐스터오일, 폴리비닐알코올, 메틸 셀룰로오스, 에틸 셀룰로오스, 하이드록시메틸 셀룰로오스, 하이드록시에틸 셀룰로오스, 하이드록시프로필 셀룰로오스, 하이드록시프로필메틸 셀룰로오스, 카르복시메틸 셀룰로오스, 덱스트린, 전분류, 폴리글리세린스테아린산에스테르, 폴리글리세린라우린산에스테르, 폴리글리세린미리스틴산에스테르, 키토산, 코코넛 아민, 스테아릴 아민, 자당스테아린산에스테르, 또는 이들의 혼합물 등을 들 수 있다.A protective colloidal compound is mixed with the reaction product. The protective colloidal compound includes a material having a hydroxy group or an amine group capable of reacting with the aliphatic isocyanate. Examples of such protective colloidal compounds are PEG-20 sorbitan monolaurate, PEG-20 sorbitan monopalmitate, PEG-20 sorbitan stearate, PEG-20 sorbitan monooleate, PEG-20 40 Hydrogenated Castor Oil, PEG-50 Hydrogenated Castor Oil, PEG-60 Hydrogenated Castor Oil, Polyvinyl Alcohol, Methyl Cellulose, Ethyl Cellulose, Hydroxymethyl Cellulose, Hydroxyethyl Cellulose, Hydroxypropyl Cellulose, hydroxypropylmethyl cellulose, carboxymethyl cellulose, dextrin, starch, polyglycerin stearate, polyglycerin laurate, polyglycerin myristate, chitosan, coconut amine, stearyl amine, sucrose stearate, or mixtures thereof; and the like.
상기 생분해성 지질계 물질과 상기 지방족계 이소시아네이트 단량체의 반응성, 인지질계 물질 수용액, 심물질의 함량 등에 따라 보호콜로이드 화합물의 사용되는 양은 달라질 수 있는데, 상기 보호콜로이드 화합물은 상기 심물질 100중량부에 대하여 1∼20중량부, 더욱 바람직하게는 1∼10중량부를 첨가하는 것이 바람직하다. 상기 보호콜로이드 화합물은 캡슐벽이 형성되는 과정에서 캡슐벽 사이가 서로 붙는 것을 억제하여 응집을 방지하는 역할을 한다. 또한, 상기 보호콜로이드 화합물은 미반응된 지방족계 이소시아네이트 단량체와 완전히 반응하여 지방족 이소시아네이트 단량체의 잔류량이 남아 있지 않게 된다. 하이드록시기를 갖는 보호콜로이드 화합물은 지방족 이소시아네이트 단량체와 반응하여 우레탄을 형성하며, 아민기를 갖는 보호콜로이드 화합물은 지방족계 이소시아네이트 단량체와 반응하여 우레아를 형성하므로, 미반응 지방족계 이소시아네이트는 완전히 제거될 수 있다.The amount of the protective colloid compound used may vary depending on the reactivity of the biodegradable lipid-based material and the aliphatic isocyanate monomer, the aqueous solution of the phospholipid-based material, the content of the core material, etc. The protective colloid compound is based on 100 parts by weight of the core material. It is preferable to add 1 to 20 parts by weight, more preferably 1 to 10 parts by weight. The protective colloidal compound serves to prevent aggregation by suppressing adhesion between capsule walls during the process of forming the capsule walls. In addition, the protective colloidal compound completely reacts with the unreacted aliphatic isocyanate monomer so that no residual amount of the aliphatic isocyanate monomer remains. Since the protective colloid compound having a hydroxy group reacts with the aliphatic isocyanate monomer to form urethane, and the protective colloid compound having an amine group reacts with the aliphatic isocyanate monomer to form urea, unreacted aliphatic isocyanate can be completely removed.
이렇게 제조된 생분해성 마이크로캡슐은 0.1∼300㎛, 더욱 바람직하게는 1∼300㎛의 크기로 제조하는 것이 바람직하며, 보다 작으면 캡슐의 기능이 원활히 발휘되기 어렵고 대량생산에 제약이 있어 경제성을 확보하기 어려울 수 있으며, 이보다 크면 캡슐의 안정성을 확보하기 어렵고 다양한 제품에 적용하는데 제약이 따를 수 있다.The biodegradable microcapsules prepared in this way are preferably manufactured in a size of 0.1 to 300 μm, more preferably 1 to 300 μm. If the size is smaller, it is difficult to perform the function of the capsule smoothly and there are restrictions on mass production to secure economic feasibility. It may be difficult to do, and if it is larger than this, it is difficult to secure the stability of the capsule and there may be restrictions on application to various products.
본 발명에 따른 생분해성 마이크로캡슐은 미량 잔류할 수 있는 지방족 이소시아네이트 단량체를 반응 가능한 보호콜로이드 화합물을 사용하여 완전히 반응시킴으로써, 인체에 자극이 될 수 있는 지방족 이소시아네이트 단량체를 제거하여 안전성을 확보하는 것이 가능하다.The biodegradable microcapsule according to the present invention completely reacts the aliphatic isocyanate monomer, which may remain in trace amounts, using a reactive protective colloidal compound, thereby removing the aliphatic isocyanate monomer, which may be irritating to the human body, to ensure safety. .
이렇게 제조된 기능성 소재용 생분해성 마이크로캡슐은, 사용 후 자연에서 분해되어 환경을 오염시키지 않고, 인체에 유해한 성분이 잔류하지 않아 피부 등의 인체에 무해하며, 기존의 캡슐과 비교하여 물리화학적 성질, 경제성 및 활용성이 향상된다. The biodegradable microcapsules for functional materials manufactured in this way do not pollute the environment as they are degraded in nature after use, and are harmless to the human body such as the skin because no harmful ingredients remain in the human body. Economic feasibility and usability are improved.
건축·토목용 자재나 화학 생활용품 등에 생분해성 마이크로캡슐의 심물질인 상변화물질, 지용성 비타민, 기능성 향료 또는 기능성 오일을 효과적으로 적용하기 위해서 고려되어야 할 점은 상변화물질, 지용성 비타민, 기능성 향료, 기능성 오일의 안정화 및 가용화이다. In order to effectively apply phase change materials, fat-soluble vitamins, functional fragrances, or functional oils, which are the core materials of biodegradable microcapsules, to building and civil engineering materials and chemical household products, the points to be considered are phase change materials, fat-soluble vitamins, functional fragrances, Stabilization and solubilization of functional oils.
상변화물질, 지용성 비타민, 기능성 오일의 가용화, 불안정한 향료 또는 오일의 안정도를 증가시키기 위하여 생분해성 캡슐로 제조함으로써 안정도를 확보하고 이를 화학제품 소재 등으로 활용할 수 있다. 공기 중에서 쉽게 휘발되거나 산화로 인하여 변질될 수 있는 불안정한 향료나 기능성 오일을 캡슐화하여 안정화시킴으로써 불안정한 향료나 기능성 오일을 화학 생활용품, 화장품 제형 등에 적용함에 있어서 발생하던 불안정성 문제를 개선할 수 있으며, 제품의 효능도 오래 지속할 수 있다. In order to solubilize phase change substances, fat-soluble vitamins, and functional oils, and to increase the stability of unstable fragrances or oils, they can be manufactured into biodegradable capsules to ensure stability and to be used as materials for chemical products. By encapsulating and stabilizing unstable fragrances or functional oils that can easily volatilize in the air or deteriorate due to oxidation, instability problems that occur when applying unstable fragrances or functional oils to chemical household products and cosmetic formulations can be improved. Efficacy can also last for a long time.
생분해성의 캡슐벽을 갖는 생분해성 마이크로캡슐은 그 내부에 심물질이 포집되어 안정화 된다. 이러한 생분해성 마이크로캡슐은 건축·토목용 자재, 액체세제, 섬유유연제 등과 같은 화학제품의 소재 뿐만 아니라, 액체제형의 샴푸, 바디소프 등 퍼스널케어 등의 액체제형의 화장품 소재로도 폭넓게 적용할 수 있다.A biodegradable microcapsule having a biodegradable capsule wall is stabilized by collecting core material therein. These biodegradable microcapsules can be widely applied not only as materials for chemical products such as building and civil engineering materials, liquid detergents, and fabric softeners, but also as liquid-type cosmetic materials such as liquid-type shampoo and body soap for personal care. .
이하에서, 본 발명에 따른 실험예들을 구체적으로 제시하며, 다음에 제시하는 실험예들에 의하여 본 발명이 한정되는 것은 아니다. Hereinafter, experimental examples according to the present invention are specifically presented, and the present invention is not limited by the experimental examples presented below.
<실험예 1><Experimental Example 1>
500㎖ 비이커에 노나데칸 100g, 생분해성 지질계 물질인 모노글리코실 세라미드(Monoglycosyl ceramide, Avati Polar Lipid Inc.社 제품) 15g을 균일하게 혼합하고, 미리 준비해둔 헥사메틸렌 디이소시아네이트 5g을 추가 혼합한 후, 인지질계 물질인 포스파티딜톨린(Phosphatidyl choline, Natural Factors 社 제품) 10g과 물 90g을 혼합하여 만든 인지질계 물질 수용액을 투입하고 호모믹서기를 사용하여 3,000rpm의 속도로 약 20분 간 교반시켜 유상/수상 에멀젼을 형성하였다. In a 500 ml beaker, 100 g of nonadecane and 15 g of monoglycosyl ceramide (Monoglycosyl ceramide, manufactured by Avati Polar Lipid Inc.), a biodegradable lipid-based material, were evenly mixed, and 5 g of hexamethylene diisocyanate prepared in advance was added and mixed. , Phosphatidyl choline (Phosphatidyl choline, a product of Natural Factors), a phospholipid-based substance, was mixed with 10 g of water and 90 g of water, and an aqueous solution of phospholipid-based substance was added and stirred for about 20 minutes at a speed of 3,000 rpm using a homomixer to form an oil/aqueous phase. An emulsion was formed.
500㎖ 4구 플라스크에 상기 유상/수상 에멀젼을 투입한 후 반응온도를 70℃로 조정한 후 약 3시간 동안 교반하면서 반응시켜 캡슐을 합성한 후, 보호콜로이드 화합물인 피이지-20소르비탄모노라우레이트 10g을 투입하여 최종적으로 생분해성 마이크로캡슐을 제조하였다.After adding the oil/aqueous emulsion to a 500 ml four-necked flask, adjusting the reaction temperature to 70 ° C, reacting with stirring for about 3 hours to synthesize a capsule, and then a protective colloidal compound, PEG-20 Sorbitan Monolau By adding 10 g of late, biodegradable microcapsules were finally prepared.
이렇게 얻어진 생분해성 마이크로캡슐의 평균 입경은 6.5㎛ 이었다. The average particle diameter of the biodegradable microcapsules thus obtained was 6.5 μm.
<실험예 2><Experimental Example 2>
생분해성 지질계 물질로서 글리코리피드(Glycolipid, RHEACEⓡOne, Evonik 社제품) 15g을 사용하는 것을 제외하고는 상기 실험예 1과 동일한 방법으로 생분해성 마이크로캡슐을 제조하였다. Biodegradable microcapsules were prepared in the same manner as in Experimental Example 1, except that 15 g of glycolipid (RHEACE ⓡ One, manufactured by Evonik) was used as a biodegradable lipid-based material.
이렇게 얻어진 생분해성 마이크로캡슐의 평균 입경은 8.3㎛ 이었다.The average particle diameter of the biodegradable microcapsules thus obtained was 8.3 μm.
<실험예 3><Experimental Example 3>
생분해성 지질계 물질로서 글루코세레브로시드(Glucocerebroside, Watson社제품) 15g을 사용하는 것을 제외하고는 상기 실험예 1과 동일한 방법으로 생분해성 마이크로캡슐을 제조하였다. Biodegradable microcapsules were prepared in the same manner as in Experimental Example 1, except that 15 g of glucocerebroside (Watson Co.) was used as a biodegradable lipid-based material.
이렇게 얻어진 생분해성 마이크로캡슐의 평균 입경은 9.7㎛ 이었다.The average particle diameter of the biodegradable microcapsules thus obtained was 9.7 μm.
<실험예 4><Experimental Example 4>
생분해성 지질계 물질로서 갱글리오시드(Ganglioside, GM2, Nagara science Co.,Ltd 社제품) 15g을 사용하는 것을 제외하고는 상기 실험예 1과 동일한 방법으로 생분해성 마이크로캡슐을 제조하였다. Biodegradable microcapsules were prepared in the same manner as in Experimental Example 1, except that 15 g of ganglioside (GM2, manufactured by Nagara Science Co., Ltd.) was used as a biodegradable lipid-based material.
이렇게 얻어진 생분해성 마이크로캡슐의 평균 입경은 5.5㎛ 이었다.The average particle diameter of the biodegradable microcapsules thus obtained was 5.5 μm.
상기 실험예들의 특성을 보다 용이하게 파악할 수 있도록 비교예를 제시하며, 아래의 비교예는 단순히 이해를 돕기 위하여 제시하는 것으로 본 발명의 선행기술이 아니다. Comparative examples are presented so that the characteristics of the above experimental examples can be more easily grasped, and the following comparative examples are simply presented to aid understanding and are not prior art of the present invention.
<비교예><Comparative example>
실험예 1 내지 실험예 4에 따른 생분해성 마이크로캡슐의 제조에 대한 비교예로서, 생분해성 물질을 사용하지 않은 일반적인 캡슐인 멜라민 마이크로캡슐의 제조를 다음과 같이 수행하였다.As a comparative example for the production of biodegradable microcapsules according to Experimental Examples 1 to 4, the preparation of melamine microcapsules, which are general capsules without using biodegradable materials, was performed as follows.
1ℓ 4구 플라스크에 멜라민 10g, 증류수 40g, 35wt% 포름알데히드 수용액 20g, 소량의 수산화나트륨을 첨가하여 pH를 8∼10으로 조절하고, 80℃에서 30분간 교반하여 멜라민-포름알데히드 전중합체(Prepolymer)를 제조하였다. Add 10 g of melamine, 40 g of distilled water, 20 g of 35 wt% formaldehyde aqueous solution, and a small amount of sodium hydroxide to a 1 liter four-necked flask to adjust the pH to 8-10, and stir at 80 ° C for 30 minutes to obtain a melamine-formaldehyde prepolymer. was manufactured.
별도의 1ℓ 비이커에 에틸렌-말레인산 공중합 수지를 5wt% 함유한 유화제 200g을 제조하고, 여기에 노나데칸 100g을 투입하여 호모믹서기를 사용해 3,500rpm의 속도로 약 20분간 교반시켜 에멀젼을 제조하였다.In a separate 1-liter beaker, 200 g of an emulsifier containing 5 wt% of ethylene-maleic acid copolymer resin was prepared, and 100 g of nonadecane was added thereto and stirred for about 20 minutes at a speed of 3,500 rpm using a homomixer to prepare an emulsion.
상기 멜라민-포름알데히드 전중합체와 상기 에멀젼을 혼합한 후, 70℃에서 2시간 동안 교반하여 멜라민 마이크로캡슐을 제조하였다. After mixing the melamine-formaldehyde prepolymer and the emulsion, they were stirred at 70° C. for 2 hours to prepare melamine microcapsules.
이렇게 얻어진 멜라민 마이크로캡슐의 평균 입경은 5.9㎛ 이었다.The average particle diameter of the melamine microcapsules thus obtained was 5.9 μm.
상기 실험예 1 내지 실험예 4, 비교예에 따라 제조한 마이크로캡슐에 대하여 생분해성, 파부자극 및 안정성에 대한 평가를 실시하였다.The microcapsules prepared according to Experimental Examples 1 to 4 and Comparative Example were evaluated for biodegradability, breakage irritation and stability.
[생분해도 측정방법 및 판정기준][Method of measuring biodegradability and criteria]
상기 실험예 1∼4, 비교예에서 제조한 각각의 마이크로캡슐을 수질-밀폐형 호흡측정계의 산소요구량 측정에 의한 액상 매질에서의 유기화합물의 호기성 최종 생분해도를 측정하는 KS I ISO 9408 및 이에 준하는 OECD 301F 방법으로 평가하였다.KS I ISO 9408 and OECD equivalent for measuring the aerobic final biodegradability of organic compounds in a liquid medium by measuring the oxygen demand of each microcapsule prepared in Experimental Examples 1 to 4 and Comparative Example. Evaluated by the 301F method.
구체적으로 생분해도 측정값에 따라 하기와 같이 표 1에 나타내었다.Specifically, it is shown in Table 1 as follows according to the measured biodegradability.
○ : 생분해도 값이 기준물질 대비 60% 이상○: Biodegradability value is 60% or more compared to the reference material
△ : 생분해도 값이 기준물질 대비 30% 이상∼60% 미만△: Biodegradability value is 30% or more to less than 60% compared to the reference material
Ⅹ : 생분해도 값이 기준물질 대비 30% 미만X: Biodegradability value is less than 30% compared to the standard substance
[피부자극 시험방법 및 평가기준][Skin irritation test method and evaluation criteria]
상기 실험예 1∼4, 비교예에서 제조한 각각의 마이크로캡슐을 피험자 31명의 등에 24시간 첩포한 후, 첩포 제거 30분, 24시간, 48시간 후에 관찰하여 국제접촉피부염학회(ICDRG) 및 미국화장품협회(PCPC) 기준을 응용한 기준에 따라 무자극/저자극/경자극/중자극/강자극으로 평가하여 표 1에 나타내었다.Each of the microcapsules prepared in Experimental Examples 1 to 4 and Comparative Example was patched on the back of 31 subjects for 24 hours, and then observed 30 minutes, 24 hours, and 48 hours after removing the patch, and the International Contact Dermatitis Society (ICDRG) and American Cosmetics According to the criteria applied with the association (PCPC) criteria, it was evaluated as non-irritating / low-irritating / light-irritating / medium-irritating / strong-stimulating, and shown in Table 1.
[안정성 시험방법 및 평가기준][Stability test method and evaluation criteria]
상기 실험예 1∼4, 비교예에서 제조한 각각의 마이크로캡슐을 40℃가 유지되는 인큐베이터에 방치한 후, 캡슐이 침전되지 않을 때까지의 시간을 측정하고 그 안정성이 유지되는 시간을 평가하여 표 1에 나타내었다.After leaving each of the microcapsules prepared in Experimental Examples 1 to 4 and Comparative Example in an incubator maintained at 40 ° C., the time until the capsules do not precipitate was measured, and the time for maintaining their stability was evaluated and the table 1.
상기 표 1에 나타낸 바와 같이, 실험예 1 내지 실험예 4의 경우가 비교예에 비해 생분해성, 피부자극 및 안정성 측면에서 모두 우수한 결과를 나타내었다. As shown in Table 1, Experimental Examples 1 to 4 showed excellent results in terms of biodegradability, skin irritation and stability compared to Comparative Examples.
이상, 본 발명의 바람직한 실시예를 들어 상세하게 설명하였으나, 본 발명은 상기 실시예에 한정되는 것은 아니며, 당 분야에서 통상의 지식을 가진 자에 의하여 여러 가지 변형이 가능하다.In the above, the preferred embodiment of the present invention has been described in detail, but the present invention is not limited to the above embodiment, and various modifications are possible by those skilled in the art.
10: 캡슐벽
20: 심물질의 유상10: capsule wall
20: Oil phase of core substance
Claims (17)
생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽을 이루고,
상기 캡슐은 0.1∼300㎛의 크기를 갖는 것을 특징으로 하는 생분해성 마이크로캡슐.
A capsule having a shape in which the capsule wall surrounds the oil phase of the heart substance,
A biodegradable polymer formed by reacting a biodegradable lipid-based material with an aliphatic isocyanate monomer forms the capsule wall of the capsule,
The capsule is a biodegradable microcapsule, characterized in that having a size of 0.1 ~ 300㎛.
The method of claim 1, wherein the biodegradable lipid-based material is biodegradable, characterized in that it comprises at least one material selected from the group consisting of sphingo lipid-based material, glycolipid-based material, sphingo glycolipid-based material and phospholipid-based material. microcapsule.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물을 포함하며,
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물을 포함하고,
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin) 또는 이들의 혼합물을 포함하는 것을 특징으로 하는 생분해성 마이크로캡슐.
The method of claim 2, wherein the sphingolipid-based material includes ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof,
The glycolipid-based material includes glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof,
The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, Contains sulfatide (sulfatide or sulfurized galactocerebroside), ganglioside, globoside or mixtures thereof;
The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin or Biodegradable microcapsules comprising a mixture thereof.
The method of claim 1, wherein the aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate (trans-1,4- Cyclohexane diisocyanate, Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-bis(isocyanomethyl)cyclohexane (1,3 -Bis (Isocyanomethyl) cyclohexane), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane (1,6-diisocyanato-2,2 ,4-trimethylhexane), 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-iso 1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane, tetramethoxybutane 1,4- diisocyanate , butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4- A biodegradable microcapsule comprising at least one material selected from the group consisting of cyclohexane 1,4-diisocyanate.
The method of claim 1, wherein the core material is at least one phase change material selected from the group consisting of nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecanestearic acid, cyanamide, propyl amide, and pentaerythritol. Biodegradable microcapsules comprising a.
The method of claim 1, wherein the heart substance is 1 selected from the group consisting of α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotachisterol, calcipotriol, tocopherol, naphthoquinone, and phylloquinone. Biodegradable microcapsules, characterized in that they contain more than one kind of fat-soluble vitamins.
The biodegradable microcapsule according to claim 1, wherein the core material includes phase change material (PCM), fat-soluble vitamins, functional flavors, functional oils, or mixtures thereof.
심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체를 혼합하는 단계;
심물질, 생분해성 지질계 물질 및 지방족계 이소시아네이트 단량체의 혼합물에 상기 심물질을 유화시킬 수 있는 인지질계 물질 수용액을 혼합하고 유화시켜 유상/수상 에멀젼이 형성되게 하는 단계;
상기 유상/수상 에멀젼에 열을 가하여 교반하면서 반응시켜 캡슐이 형성되게 하는 단계; 및
상기 반응 결과물에 보호콜로이드 화합물을 혼합하는 단계를 포함하며,
생분해성 지질계 물질과 지방족계 이소시아네이트 단량체가 반응하여 형성된 생분해성 폴리머가 상기 캡슐의 캡슐벽을 이루고,
상기 캡슐은 0.1∼300㎛의 크기를 갖는 것을 특징으로 하는 생분해성 마이크로캡슐의 제조방법.
A method for producing a capsule having a shape in which the capsule wall surrounds the oil phase of the core substance,
mixing a core material, a biodegradable lipid-based material, and an aliphatic isocyanate monomer;
Mixing and emulsifying an aqueous solution of a phospholipid-based material capable of emulsifying the core material with a mixture of a core material, a biodegradable lipid-based material, and an aliphatic isocyanate monomer to form an oil/water phase emulsion;
Applying heat to the oil/aqueous emulsion to react while stirring to form capsules; and
Mixing a protective colloidal compound with the reaction product,
A biodegradable polymer formed by reacting a biodegradable lipid-based material with an aliphatic isocyanate monomer forms the capsule wall of the capsule,
The method of producing a biodegradable microcapsule, characterized in that the capsule has a size of 0.1 ~ 300㎛.
The method of claim 8, wherein the biodegradable lipid-based material is biodegradable, characterized in that it comprises at least one material selected from the group consisting of sphingo lipid-based material, glycolipid-based material, sphingo glycolipid-based material and phospholipid-based material Manufacturing method of microcapsules.
상기 당지질계 물질은 글리세르당지질, 갈락토지질(galatolipid), 황지질(sulfolipid) 또는 이들의 혼합물을 포함하며,
상기 스핑고 당지질계 물질은 글리코리피드(Glycolipid), 세레브로시드(Cerebroside), 글루코세레브로시드(Glucocerebroside), 모노글리코실세라미드(monoglycosylceramide), 갈락토세레브로시드(galactocerebroside), 포도당세레브로시드, 설파타이드(sulfatide 또는 황화 갈락토세레브로시드), 갱글리오시드(Ganglioside), 글로보시드(Globoside) 또는 이들의 혼합물을 포함하고,
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin), 세팔린(Cephalin) 또는 이들의 혼합물을 포함하는 것을 특징으로 하는 생분해성 마이크로캡슐의 제조방법.
10. The method of claim 9, wherein the sphingolipid-based material includes ceramide, phytoceramide, sphingomyelin, cerebroside, ganglioside, or a mixture thereof,
The glycolipid-based material includes glycerol glycolipids, galatolipids, sulfolipids, or mixtures thereof,
The sphingo glycolipid-based substance is glycolipid, cerebroside, glucocerebroside, monoglycosylceramide, galactocerebroside, glucose cerebroside, Contains sulfatide (sulfatide or sulfurized galactocerebroside), ganglioside, globoside or mixtures thereof;
The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin, cephalin or A method for producing biodegradable microcapsules comprising a mixture thereof.
The method of claim 8, wherein the aliphatic isocyanate monomer is 4,4'-dicyclohexylmethane diisocyanate, trans-1,4-cyclohexane diisocyanate (trans-1,4- Cyclohexane diisocyanate, Isophorone diisocyanate, Hexamethylene diisocyanate, Trimethyl hexamethylene diisocyanate, 1,3-bis(isocyanomethyl)cyclohexane (1,3 -Bis (Isocyanomethyl) cyclohexane), 2.4-diisocyanato cyclohexane, 1,6-diisocyanato-2,2,4-trimethylhexane (1,6-diisocyanato-2,2 ,4-trimethylhexane), 1,6-diisocyanato-2,4,4-trimethylhexane (1,6-diisocyanato-2,4,4-trimethylhexane), 1-isocyanatomethyl-3-iso 1-isocyanatomethyl-3-isocyanato-l,5,5-trimethyl cyclohexane, tetramethoxybutane 1,4- diisocyanate , butane 1,4-diisocyanate, hexane 1,6- diisocyanate, dicyclohexylmethane diisocyanate and cyclohexane 1,4- A method for producing biodegradable microcapsules comprising at least one material selected from the group consisting of diisocyanate (cyclohexane 1,4-diisocyanate).
상기 지방족계 이소시아네이트 단량체는 심물질 100중량부에 대하여 0.1∼10중량부를 혼합하는 것을 특징으로 하는 생분해성 마이크로캡슐의 제조방법.
The method of claim 8, wherein the biodegradable lipid-based material is mixed with 1 to 20 parts by weight based on 100 parts by weight of the core material,
The aliphatic isocyanate monomer is a method for producing biodegradable microcapsules, characterized in that 0.1 to 10 parts by weight is mixed with respect to 100 parts by weight of the core material.
상기 인지질계 물질은 포스파티딜콜린(phosphatidyl choline), 포스파티딘산(phosphatidic acid), 포스파티딜에탄올아민(phosphatidylethanolamine), 포스파티딜세린(phosphatidylserine), 포스파티딜이노시톨, 다이포스파티딜글리세롤, 레시틴(Lecithin) 및 세팔린(Cephalin)으로 이루어진 군으로부터 선택된 1종 이상의 물질을 포함하는 것을 특징으로 하는 생분해성 마이크로캡슐의 제조방법.
The method of claim 8, wherein the aqueous solution of the phospholipid-based material is an aqueous solution prepared by mixing 1 to 10 parts by weight of the phospholipid-based material with respect to 100 parts by weight of the core material and adding 10 to 90 parts by weight of water with respect to 100 parts by weight of the core material,
The phospholipid-based material is phosphatidyl choline, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, diphosphatidylglycerol, lecithin and cephalin. A method for producing biodegradable microcapsules comprising at least one material selected from the group consisting of:
9. The method of claim 8, wherein the protective colloidal compound comprises a material having a hydroxy group or an amine group capable of reacting with the aliphatic isocyanate monomer.
The method of claim 8, wherein the core material is at least one phase change material selected from the group consisting of nonadecane, octadecane, heptadecane, hexadecane, tetradecane, pentadecanestearic acid, cyanamide, propyl amide and pentaerythritol Method for producing biodegradable microcapsules comprising a.
The method of claim 8, wherein the heart substance is α-carotene, β-carotene, retinol, tretinoin, alphacalcidol, dihydrotachisterol, calcipotriol, tocopherol, naphthoquinone and phylloquinone selected from the group consisting of 1 A method for producing biodegradable microcapsules comprising at least one fat-soluble vitamin.
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