CN106074716B - tea tree oil microcapsule and preparation method and application thereof - Google Patents
tea tree oil microcapsule and preparation method and application thereof Download PDFInfo
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- CN106074716B CN106074716B CN201610511923.2A CN201610511923A CN106074716B CN 106074716 B CN106074716 B CN 106074716B CN 201610511923 A CN201610511923 A CN 201610511923A CN 106074716 B CN106074716 B CN 106074716B
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- 239000010677 tea tree oil Substances 0.000 title claims abstract description 88
- 229940111630 tea tree oil Drugs 0.000 title claims abstract description 88
- 239000003094 microcapsule Substances 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000003756 stirring Methods 0.000 claims abstract description 42
- 229920001807 Urea-formaldehyde Polymers 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 18
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 239000013067 intermediate product Substances 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 9
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
- 239000003995 emulsifying agent Substances 0.000 claims description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004659 sterilization and disinfection Methods 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 244000183278 Nephelium litchi Species 0.000 claims description 2
- 238000004378 air conditioning Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 14
- 229940079593 drug Drugs 0.000 description 13
- 238000011068 loading method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000013268 sustained release Methods 0.000 description 7
- 239000012730 sustained-release form Substances 0.000 description 7
- 239000000341 volatile oil Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- -1 terpene compounds Chemical class 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 229930006739 camphene Natural products 0.000 description 2
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 208000035404 Autolysis Diseases 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010005913 Body tinea Diseases 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010057248 Cell death Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 244000011376 Leptospermum laevigatum Species 0.000 description 1
- 235000017865 Leptospermum laevigatum Nutrition 0.000 description 1
- 241000378467 Melaleuca Species 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241001148134 Veillonella Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 125000000567 diterpene group Chemical group 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- KKOXKGNSUHTUBV-UHFFFAOYSA-N racemic zingiberene Natural products CC(C)=CCCC(C)C1CC=C(C)C=C1 KKOXKGNSUHTUBV-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000028043 self proteolysis Effects 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 201000003875 tinea corporis Diseases 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- KKOXKGNSUHTUBV-LSDHHAIUSA-N zingiberene Chemical compound CC(C)=CCC[C@H](C)[C@H]1CC=C(C)C=C1 KKOXKGNSUHTUBV-LSDHHAIUSA-N 0.000 description 1
- 229930001895 zingiberene Natural products 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/28—Myrtaceae [Myrtle family], e.g. teatree or clove
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Zoology (AREA)
- Mycology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Biotechnology (AREA)
- Public Health (AREA)
- Botany (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
the invention relates to the technical field of modified materials, and discloses a tea tree oil microcapsule and a preparation method thereof, wherein the preparation method comprises the steps of S2, uniformly stirring urea-formaldehyde resin prepolymer of S1, sodium dodecyl sulfate and water at normal temperature to obtain a first mixture, S3, dissolving tea tree oil in absolute ethyl alcohol, slowly adding the mixture into the first mixture, stirring for 10 ~ 20min, adjusting the pH value of the system and stirring process, heating the system to 30 ~ 35 ℃, curing for 80 ~ 120min, and filtering to obtain an intermediate product, wherein the mass ratio of the tea tree oil to the absolute ethyl alcohol is (8 ~ 15) to (1 ~ 5) to (3 ~ 6), and the mass of the sodium dodecyl sulfate is 1% to ~ 4% of the total mass of the urea-formaldehyde resin prepolymer.
Description
Technical Field
the invention relates to the technical field of microcapsules, and particularly relates to a tea tree oil microcapsule and a preparation method and application thereof.
Background
tea tree oil is an aromatic essential oil prepared by distilling branches and leaves of Melaleuca. It contains hundreds of chemical components, is a natural mixture with extremely complex composition, and the basic components of the natural mixture are roughly divided into four types: (ii) terpene compounds: is the main chemical component of plant essential oil, has a molecular formula of chain or cyclic olefin of isoprene structural unit, has simple multiple relation with isoprene, and can be written as (C)5H8) n is the same as the formula (I). Terpenes are in various types and have various isomers, and can be classified into hemiterpenes, monoterpenes (e.g., pinene, limonene, myrcene, camphene), sesquiterpenes (e.g., zingiberene), diterpenes (e.g., camphene), polyterpenes, etc. according to their structures. (II) aromatic Compound: the compounds are the second compounds of the plant essential oil, and are mainly divided into two types: terpene-derived derivatives and phenylpropane derivatives. ③ aliphatic compounds: including alkenes, alkanes, alcohols, etc., are the compounds with the smallest molecular weight in plant essential oils, and almost all essential oils contain the compounds, but the contents are small and the essential oils are not the main components. Nitrogen-containing and sulfur-containing compounds: these compounds generally have an irritating odor and are present in relatively low levels in plant essential oils.
Tea tree oil is one of natural antibacterial preparations which are scientifically certified, and the antibacterial activity of the tea tree oil is widely researched and applied. Is widely applied in the fields of life, medicine and cosmetics. The tea tree oil has been reported to have good bacteriostatic activity on gram strains such as candida albicans, staphylococcus aureus, escherichia coli, pseudomonas aeruginosa and the like and 24 fungi. In the study of the antibacterial mechanism of tea tree oil, the tea tree oil is found to increase the permeability of the somatic intercellular substance, so that cells are disintegrated and die by autolysis. The tea tree oil has good antiviral activity besides antibacterial activity, can effectively treat varicella, and at present, as the varieties of the tea tree oil introduced in China are increased and are greatly different from the chemical components of Australian tea tree oil, most of the tea tree oil species in China also have good broad-spectrum antibacterial activity, and the research proves that the tea tree oil produced in China has good antibacterial effect on strains such as staphylococcus aureus, Escherichia coli, bacillus subtilis, pseudomonas aeruginosa and the like; hammer et al research proves that the minimum inhibitory concentration of the tea tree oil is between 0.003% and 2.0%, and the tea tree oil has strong inactivation effect on oral pathogenic bacteria such as actinomycetes, lactobacillus, veillonella and the like; the research of handsome and the like proves that the tea tree oil produced in China has the inhibition effect on the aspergillus niger. Due to the excellent antibacterial activity of tea tree oil, the tea tree oil is commonly used for treating tinea pedis, acne, tinea corporis, face sore and skin diseases caused by bacterial infection in medicines and cosmetics, and improving oil secretion of skin, and is mainly used as an antiseptic antibacterial agent and a flavoring agent in the aspects of food, widely used for meat products, fish eggs, fruits, vegetables, frozen food and the like, and also used as an air freshener, a household hospital, tableware sanitary disinfection, pet products and the like.
However, tea tree oil is volatile, unstable, and inconvenient to transport, store, and use. Therefore, a tea tree oil storage mode is needed, waste of the tea tree oil is reduced, the antibacterial effect of the tea tree oil is better exerted, and resources are fully and effectively utilized.
Disclosure of Invention
The invention aims to solve the technical problem of the existing tea tree oil and provides a tea tree oil microcapsule which has uniform particle size distribution, smooth and full particles, high drug loading rate up to 45 percent and good slow release effect.
The invention also aims to provide a preparation method of the tea tree oil microcapsule.
The invention also aims to provide application of the tea tree oil microcapsule.
the above object of the present invention is solved by the following technical means:
A preparation method of tea tree oil microcapsules is characterized by comprising the following steps:
s1, preparing a urea-formaldehyde resin prepolymer by reacting formaldehyde and urea;
S2, uniformly stirring the urea-formaldehyde resin prepolymer of S1, an emulsifier and water at normal temperature to obtain a first mixture;
S3, dissolving the tea tree oil in absolute ethyl alcohol, slowly adding the tea tree oil into the first mixture, stirring and reacting, and then adjusting the pH value of the system to be 3-6 to continue stirring and reacting; then adjusting the pH value of the system to 2.5-3.5, and continuously stirring for reaction; adjusting the pH value to 1-3 again, and continuously stirring for reaction; then heating the system to 30-35 ℃, curing for 80-120 min, and filtering to obtain an intermediate product;
s4, drying the intermediate product at 35-45 ℃ to obtain the tea tree oil microcapsule;
urea-formaldehyde resin prepolymer: tea tree oil: the mass ratio of the absolute ethyl alcohol is (8-15) to (1-5) to (3-6), and the mass of the emulsifier is 1-4% of the total mass of the urea resin prepolymer.
The emulsifier includes, but is not limited to, tween 20, tween 80, sodium dodecylbenzenesulfonate, sodium dodecylsulfate, sodium polyacrylate, sodium sulfosuccinate, sodium carboxymethylcellulose, etc.
In the invention, in-situ polymerization is adopted, under the action of an emulsifier, core material tea tree oil is uniformly dispersed in a water phase, urea-formaldehyde resin prepolymer is dissolved in water, urea-formaldehyde resin with a cross-linked structure is gradually formed along with the progress of polymerization reaction, and is separated out from the water phase and deposited on the surface of the core material, thereby forming the microcapsule. The reaction mechanism is as follows: (1) hydroxymethylation (prepolymerization stage): under the condition of alkalescence, formaldehyde and urea are firstly subjected to addition reaction to generate urea-formaldehyde resin prepolymer. (2) And (3) resin reaction: the stage is condensation polymerization, under the weak acidity condition, active hydroxymethyl in the urea resin prepolymer can be subjected to dehydration condensation reaction with active hydrogen connected with nitrogen atoms in urea or hydroxymethyl urea molecules, and the condensation polymerization enables generated urea precursors to be connected in a methylene bond mode to generate a polymer with a linear structure.
The tea tree oil has the characteristics of easy volatilization, instability and the like. According to the invention, in the process of preparing the microcapsule, the pH conditions of the urea resin prepolymer and tea tree oil at different stages of the mixing reaction are creatively controlled, and the combination of the type, the amount and the curing time of the emulsifier is adopted, so that a polymer uniformly covered on the surface of tea tree oil particles is formed, and the microcapsule with high drug loading capacity, uniform particle size and good sustained release effect is obtained.
Preferably, the reaction of S3 is carried out in the absence of light to reduce the effect of light on the structure of tea tree oil.
preferably, the mass ratio of the formaldehyde to the urea in the S1 is 2.5-2: 1.
Preferably, in S1, formaldehyde and urea are heated and reacted for 1-2 h under the condition that the pH value is 8 and the temperature is 70 ℃.
Preferably, the urea-formaldehyde resin prepolymer, the sodium dodecyl sulfate and the water in the S2 are stirred for 15min at the normal temperature and the rotating speed of 1000 r/min.
preferably, the urea resin prepolymer: tea tree oil: the mass ratio of the absolute ethyl alcohol is (8-15) to (1-5) to (3-6), and the mass of the emulsifier is 4% of the total mass of the urea resin prepolymer.
Preferably, the urea resin prepolymer: tea tree oil: the mass ratio of the absolute ethyl alcohol is 12:3:6, and the mass of the emulsifier is 4% of the total mass of the urea resin prepolymer. Preferably, S3, dissolving the tea tree oil in absolute ethyl alcohol, slowly adding the tea tree oil into the first mixture, and stirring for 10-30min, wherein the rotating speed of a stirrer is 800-; then adjusting the pH value of the system to 3-6, and continuously stirring for 10-20 min; then adjusting the pH value of the system to 2.5-3.5, and stirring for 10-30min at the rotating speed of the stirrer of 300-; adjusting the pH value to 1-3 again, and continuing stirring for 20-60 min; and then heating the system to 30-35 ℃, curing for 80-120 min, and filtering to obtain an intermediate product.
Preferably, S3, dissolving the tea tree oil in absolute ethyl alcohol, slowly adding the tea tree oil into the first mixture, stirring for 15-20 min, wherein the rotation speed of a stirrer is 800r/min, then adjusting the pH value of the system to 4.5-5.5, and continuously stirring for 10-20 min; then adjusting the pH value of the system to 2.5-3.5, controlling the rotating speed of a stirrer to 300r/min, and continuously stirring for 15-20 min; adjusting the pH value to 1.8-2.2 again, and continuing stirring for 25-35 min; then heating the system to 30-35 ℃, curing for 80-120 min, and filtering to obtain an intermediate product;
Preferably, S3, dissolving the tea tree oil in absolute ethyl alcohol, slowly adding the tea tree oil into the first mixture, and stirring for 15min, wherein the rotating speed of a stirrer is 800 r/min; then adjusting the pH value of the system to 5, and continuing stirring for 15 min; then adjusting the pH value of the system to 3, and stirring for 15min at the rotating speed of the stirrer of 300 r/min; adjusting the pH value to 2 again, and continuing stirring for 30 min; and then heating the system to 30-35 ℃, curing for 80min, and filtering to obtain an intermediate product.
An application of the tea tree oil microcapsule in litchi preservation, medical sterilization and vehicle air-conditioning outlet sterilization.
Compared with the prior art, the invention has the following beneficial effects:
The preparation method of the tea tree oil microcapsule can effectively overcome the volatile and unstable properties of tea tree oil, the prepared tea tree oil microcapsule has uniform particle size distribution, smooth and full particles and the drug loading rate of 45 percent; the sustained-release effect is good, the sustained release tends to be balanced when the sustained-release time reaches 50h, and the maximum sustained-release amount is 50.2%.
Drawings
FIG. 1 is a diagram of microcapsules prepared with different amounts of emulsifier.
Detailed Description
the present invention is further explained and illustrated with reference to the following specific examples, which are not intended to limit the present invention in any way. In the following examples, the drugs and equipment used are commercially available products.
In the following examples, the test methods for microcapsule properties are as follows:
1. Determination of microcapsule sustained Release Properties
The sustained release amount of the microcapsule is measured by an ultraviolet spectrophotometer, and the method comprises the following steps: (1) absolute ethyl alcohol is used as a solvent, tea tree oil solutions with different concentrations are prepared, and an ultraviolet spectrophotometer is used for measuring a standard working curve equation of the tea tree oil under the condition that the maximum absorption wavelength is 266nm, wherein the standard working curve equation is as follows: c-205.99 a + 3.4718. (2) Weighing a certain amount of dried microcapsule sample respectively, placing the microcapsule sample in 100mL conical flasks, transferring 1mL of tea tree oil solution from each conical flask into a 50mL volumetric flask at fixed time intervals, and metering the volume to a scale mark by using absolute ethyl alcohol. (3) Then, 1mL of absolute ethanol was added back to each flask. (4) The absorbance A of each sample was measured at a wavelength of 266nm with an ultraviolet spectrophotometer. The cumulative amount of microcapsules released was calculated as follows.
The formula for calculating the cumulative release amount Ri of the microcapsule is as follows:
where rhoithe concentration of tea tree oil in the solution taken out for the ith time (mg. L-1); LC is the drug loading of the microcapsule; mi is the mass of the microcapsule.
2. determination of microcapsule drug loading
Similar to the test of the slow release performance, a certain mass of microcapsules are placed in conical flasks added with 100mL of absolute ethyl alcohol, after ultrasonic oscillation for 10min, the conical flasks are kept stand for 24h, 1mL of microcapsules are transferred into a 25mL volumetric flask, absolute ethyl alcohol is used for fixing the volume to a scale, and the absorbance of each sample is measured by an ultraviolet spectrophotometer. The drug loading rate calculation formula is as follows:
Wherein c is the measured final concentration of each sample, mg.L < -1 >; b is the dilution multiple; m is the weight of the weighed microcapsule.
Example 1
A preparation method of tea tree oil microcapsules comprises the following steps:
S1, weighing 30g of urea, 70.9g of formaldehyde and 126g of water in a three-neck flask, adjusting the pH value of the system to be 8 by using triethanolamine, and heating for 1h in an oil bath kettle at 70 ℃, wherein the obtained colorless liquid is the urea-formaldehyde resin prepolymer.
S2, weighing 12g of urea-formaldehyde resin prepolymer and 0.48g of sodium dodecyl sulfate in a beaker with 20ml of water, and stirring for 15min by using a magnetic stirrer at normal temperature at the rotating speed of 1000r/min to obtain a first mixture;
S3.1) dissolving 3g of tea tree oil in 6g of absolute ethyl alcohol, dropwise adding the tea tree oil into the first mixture, adjusting the rotating speed of a magnetic stirrer to be 800r/min, and stirring for 15 min; 2) then adjusting the pH value of the system to 5, and continuing stirring for 15 min; 3) regulating the rotation speed to 300r/min and the pH value of the regulating system to be 3, stirring for 15min, then continuously regulating the pH value of the regulating system to be 2, and stirring for 30 min; 4) heating the system to 30-35 ℃, and curing for 80 min.
S4, performing suction filtration by using a sand core funnel, putting the obtained product into a vacuum drying oven at 40 ℃, and completely drying for 24 hours to obtain white powder, namely the tea tree oil microcapsule.
Examples 2 to 4
The main steps of examples 2 to 4 are the same as those of example 1, except that the process conditions of steps S1 to S4, and the specific parameters are shown in Table 1.
TABLE 1
Comparative examples 1 to 4
the main steps of comparative examples 1 to 4 are the same as in example 1, except that the amount of the emulsifier used in step S2 is different, and the specific parameters are shown in Table 2.
TABLE 2
The tea tree oil microcapsules prepared in the above examples and comparative examples are used for measuring the slow release performance and drug loading rate, and the test results are as follows:
Because the emulsifier is the premise of preparing the microcapsule, the addition of the emulsifier ensures that the oil and the water are not layered, and the tea tree oil is uniformly dispersed in the continuous phase to form stable and uniform emulsion.
As can be seen from FIG. 1, the amount of the emulsifier used in example 1 is different from that used in comparative examples 1-2, and the morphology of the prepared microcapsule has a large difference. When the content of the emulsifier is less than 1% or exceeds 4%, a large amount of fragments are obviously accumulated on the surface of the obtained microcapsule, and the particles are unevenly distributed and are in an agglomerated state.
It can be seen from table 3 that when the emulsifier content was 4% of the prepolymer, the amount of tea tree oil coating reached 45%. The surface tension between oil and water can be better reduced by a proper amount of emulsifier, oil drops are fully dispersed in the continuous phase, and the urea resin can be deposited on the surfaces of a large number of oil drops to generate polymerization coating of the oil drops. In the preparation process of the microcapsule, as the tea tree oil is volatile, part of the tea tree oil is lost in the preparation process, so that the integral coating rate is not very high.
TABLE 3 Effect of emulsifier dosage on drug Loading
Table 4 reflects the effect of cure time on microcapsule loading. Because of the volatility of tea tree oil, when the curing time is prolonged, the more tea tree oil that volatilizes, lead to the tea tree oil to lose in a large number for the drug loading reduces, and when the curing time is 160min, the drug loading reaches minimum, and the tea tree oil loss is more serious.
TABLE 4 Effect of curing time on drug loading
| Serial number | curing time/min | LC/％ |
| Comparative example 5 | 40 | 28.84 |
| Example 1 | 80 | 36.56 |
| Example 3 | 120 | 32.19 |
| Comparative example 6 | 160 | 22.53 |
When the content of the emulsifier accounts for 3 percent of the content of the prepolymer, the slow release tends to be balanced when the slow release time reaches 55 hours, and the maximum release content is 29.5 percent. However, when the content of the emulsifier accounts for 4% of the content of the prepolymer, the slow release tends to be balanced when the slow release time reaches 50h, and the maximum slow release amount is 50.2%.
when the curing time is 160min, the slow release reaches the balance when the slow release time is 70h, and the accumulated release Ri amount is 30%. When the curing time is 80min and 120min, the slow release reaches the balance when the slow release time is 65h, and the cumulative release amount Ri is 57 percent and 68 percent respectively.
Claims (10)
1. A preparation method of tea tree oil microcapsules is characterized by comprising the following steps:
S1, preparing a urea-formaldehyde resin prepolymer by reacting formaldehyde and urea;
S2, uniformly stirring the urea-formaldehyde resin prepolymer of S1, an emulsifier and water at normal temperature to obtain a first mixture;
S3, dissolving the tea tree oil in absolute ethyl alcohol, slowly adding the tea tree oil into the first mixture, stirring and reacting, and then adjusting the pH value of the system to be 3-6 to continue stirring and reacting; then adjusting the pH value of the system to 2.5-3.5, and continuously stirring for reaction; adjusting the pH value to 1-3 again, and continuously stirring for reaction; then heating the system to 30-35 ℃, curing for 80-120 min, and filtering to obtain an intermediate product;
S4, drying the intermediate product at 35-45 ℃ to obtain the tea tree oil microcapsule;
Urea-formaldehyde resin prepolymer: tea tree oil: the mass ratio of the absolute ethyl alcohol is (8-15) to (1-5) to (3-6), and the mass of the emulsifier is 1-4% of the total mass of the urea resin prepolymer.
2. The preparation method of the tea tree oil microcapsule as claimed in claim 1, wherein the mass ratio of formaldehyde to urea in S1 is 2.5-2: 1.
3. The preparation method of the tea tree oil microcapsule as claimed in claim 2, wherein the formaldehyde in S1 is reacted with urea at 70 ℃ at pH 8 for 1-2 h.
4. the preparation method of the tea tree oil microcapsule as claimed in claim 1, wherein the urea formaldehyde resin prepolymer, the sodium dodecyl sulfate and the water in the S2 are stirred at the normal temperature of 1000r/min for 15 min.
5. The method for preparing tea tree oil microcapsules according to claim 1, wherein the urea resin prepolymer: tea tree oil: the mass ratio of the absolute ethyl alcohol is (8-15) to (1-5) to (3-6), and the mass of the emulsifier is 4% of the total mass of the urea resin prepolymer.
6. The preparation method of the tea tree oil microcapsule as claimed in claim 1, wherein S3. dissolving tea tree oil in absolute ethanol, slowly adding into the first mixture and stirring for 10-30min, wherein the rotation speed of the stirrer is 800-; then adjusting the pH value of the system to 3-6, and continuously stirring for 10-20 min; then adjusting the pH value of the system to 2.5-3.5, and stirring for 10-30min at the rotating speed of the stirrer of 300-; adjusting the pH value to 1-3 again, and continuing stirring for 20-60 min; and then heating the system to 30-35 ℃, curing for 80-120 min, and filtering to obtain an intermediate product.
7. The preparation method of the tea tree oil microcapsule as claimed in claim 6, wherein S3. dissolving tea tree oil in absolute ethyl alcohol, slowly adding the tea tree oil into the first mixture, stirring for 15-20 min at a rotation speed of 800r/min, adjusting the pH of the system to 4.5-5.5, and continuously stirring for 10-20 min; then adjusting the pH value of the system to 2.5-3.5, controlling the rotating speed of a stirrer to 300r/min, and continuously stirring for 15-20 min; adjusting the pH value to 1.8-2.2 again, and continuing stirring for 25-35 min; and then heating the system to 30-35 ℃, curing for 80-120 min, and filtering to obtain an intermediate product.
8. The preparation method of the tea tree oil microcapsule as claimed in claim 6, wherein S3. dissolving tea tree oil in absolute ethanol, slowly adding into the first mixture and stirring for 15min, wherein the rotation speed of the stirrer is 800 r/min; then adjusting the pH value of the system to 5, and continuing stirring for 15 min; then adjusting the pH value of the system to 3, and stirring for 15min at the rotating speed of the stirrer of 300 r/min; adjusting the pH value to 2 again, and continuing stirring for 30 min; and then heating the system to 30-35 ℃, curing for 80min, and filtering to obtain an intermediate product.
9. A tea tree oil microcapsule prepared by the process according to any one of claims 1 to 8.
10. An application of the tea tree oil microcapsule of claim 9 in litchi fresh-keeping, medical sterilization and vehicle air-conditioning outlet sterilization.
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