WO2023124920A1 - Method for preparing modified antifungal liquid from natural plants and product thereof - Google Patents
Method for preparing modified antifungal liquid from natural plants and product thereof Download PDFInfo
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- WO2023124920A1 WO2023124920A1 PCT/CN2022/138168 CN2022138168W WO2023124920A1 WO 2023124920 A1 WO2023124920 A1 WO 2023124920A1 CN 2022138168 W CN2022138168 W CN 2022138168W WO 2023124920 A1 WO2023124920 A1 WO 2023124920A1
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- 239000007788 liquid Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title abstract description 5
- 230000000843 anti-fungal effect Effects 0.000 title abstract 5
- 229940121375 antifungal agent Drugs 0.000 title abstract 5
- 239000002131 composite material Substances 0.000 claims abstract description 8
- 241000196324 Embryophyta Species 0.000 claims description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
- 230000000844 anti-bacterial effect Effects 0.000 claims description 49
- 238000000605 extraction Methods 0.000 claims description 38
- 238000000194 supercritical-fluid extraction Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 16
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 11
- 235000001855 Portulaca oleracea Nutrition 0.000 claims description 10
- 241000219304 Portulacaceae Species 0.000 claims description 10
- -1 3-chloro-2-hydroxypropyltrimethylammonium halide Chemical class 0.000 claims description 9
- 239000003607 modifier Substances 0.000 claims description 9
- 244000107368 Viola confusa Species 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 241001104043 Syringa Species 0.000 claims description 6
- 235000004338 Syringa vulgaris Nutrition 0.000 claims description 6
- 244000223014 Syzygium aromaticum Species 0.000 claims description 4
- 235000016639 Syzygium aromaticum Nutrition 0.000 claims description 4
- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 abstract description 2
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 241000405217 Viola <butterfly> Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 229930182486 flavonoid glycoside Natural products 0.000 description 1
- 150000007955 flavonoid glycosides Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
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- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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]
-
- 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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
Definitions
- the invention belongs to the field of antibacterial agents, and in particular relates to a preparation method of a natural plant modified antibacterial liquid and a product thereof.
- the purpose of the present invention is to provide a preparation method of natural plant modified antibacterial liquid.
- Another object of the present invention is to provide a natural plant modified antibacterial liquid product prepared according to the above method.
- a kind of preparation method of natural plant modified antibacterial liquid is characterized in that, comprises the following steps:
- Step 1 according to the mass ratio of 1:0.4 ⁇ 1.5:0.6 ⁇ 1.0, put the dried clove flower buds, the whole plant of purslane and the whole plant of Viola chinensis into the pulverizer for crushing, and then add it to the supercritical extraction kettle Carry out supercritical extraction in the medium, use CO 2 as extractant, ethanol solution as entrainer, obtain ethanol plant composite extract after extraction is finished;
- step 2 the ethanol-plant composite extract obtained in step 1 is added to the reaction vessel, and L-hydroxyproline is added.
- the amount of L-hydroxyproline is 1%-5% of the total mass of the ethanol-plant composite extract.
- After the reaction add 3-chloro-2-hydroxypropyltrimethylammonium halide modifier and reflux for 12 hours.
- 3-chloro-2-hydroxypropyltrimethylammonium halide The ratio of the molar dosage of the ammonium modifier to the molar dosage of L-hydroxyproline is 0.5-0.95:1 to obtain the natural plant modified antibacterial liquid.
- the extraction pressure is 30-40MPa
- the extraction temperature is 35°C-45°C
- the extraction time is 2-4 hours.
- the concentration of the ethanol solution of the entrainer is 85%-95%.
- the present invention selects lilac flower buds, whole herb of purslane and viola as main antibacterial plants, lilac buds contain eugenol, which has plant aroma and obvious antibacterial and virus-killing effects, and purslane contains flavonoid compounds, which have antiallergic effects , has a good inhibitory effect on Escherichia coli, and the flavonoid glycosides and organic acids in the Viola extract have the most obvious antibacterial and bactericidal effects on Staphylococcus aureus.
- the present invention uses supercritical extraction to extract the three plants to obtain The ethanol plant compound extract is then reacted with L-hydroxyproline. L-hydroxyproline is a food additive.
- the carboxyl and hydroxyl bifunctional groups in the molecular structure can be combined with the hydroxyl and carboxylic acid in the ethanol plant compound extract.
- the grafted compound containing secondary amine groups is obtained through the grafting reaction of the functional groups.
- the grafted secondary amine compound is modified with a halogen-containing modifier to form a cationic quaternary ammonium salt, which further improves the bactericidal and antibacterial properties of the composite extract.
- the advantage of adding L-hydroxyproline in the present invention is that L-hydroxyproline is used as a food flavoring agent, which has high safety. After grafting with the ethanol plant compound extract, the secondary amino group can be combined with the halogen functional group of the modifier.
- a substitution reaction occurs, and the carboxylic acid group can react with the hydroxyl group of the modifier, which can greatly improve the grafting effect of the 3-chloro-2-hydroxypropyltrimethylammonium halide cationic etherification agent, and greatly improve the natural plant
- the bactericidal effect of the extract, and the modified product has low irritation and high safety. It can be used as a bactericide for daily chemicals, lotion products and industrial coatings, and has a wide range of applications.
- the invention modifies the extracted natural plant antibacterial liquid to obtain a compound antibacterial liquid with good bactericidal performance and high safety, the process is simple, the obtained modified antibacterial liquid has little environmental stimulation and wide application fields.
- a kind of natural plant modified antibacterial liquid prepared according to the following steps:
- Step 1 put dried 50g clove flower buds, 40g whole plant of purslane dentata and 30g whole plant of Viola chinensis into a pulverizer for pulverization, then add them into a supercritical extraction kettle for supercritical extraction, using CO2 for The extraction agent, the ethanol entrainer concentration is 95%, the extraction pressure is 35MPa, the extraction temperature is 45°C, the extraction time is 2 hours, and 28g of ethanol plant compound extract is obtained after the extraction is completed;
- Step 2 Add 28g of the ethanol plant compound extract obtained in Step 1 into the reaction vessel, add 0.8g of L-hydroxyproline, and react at 60°C for 6 hours. After the reaction, add 0.9g of 3-chloro -2-Hydroxypropyltrimethylammonium halide modifier was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K1.
- a kind of natural plant modified antibacterial liquid prepared according to the following steps:
- Step 1 put 50g of dried lilac flower buds, 60g of whole plant of purslane dentata and 40g of whole plant of Viola chinensis into a pulverizer for crushing, and then put them into a supercritical extraction kettle for supercritical extraction, using CO2 as the extraction agent, the ethanol entrainer concentration is 85%, the extraction pressure is 35MPa, the extraction temperature is 40°C, the extraction time is 2.5 hours, and 40g of ethanol plant compound extract is obtained after the extraction is completed;
- Step 2 Add 40.0g of ethanol plant compound extract to the reaction vessel, add 1.1g of L-hydroxyproline, and react at 60°C for 6 hours. After the reaction, add 1.2g of 3-chloro-2-hydroxypropyl Trimethyl ammonium chloride was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K2.
- a kind of natural plant modified antibacterial liquid prepared according to the following steps:
- Step 1 put 40g of dried lilac flower buds, 60g of whole plant of purslane dentata and 40g of whole plant of Viola chinensis into a pulverizer for crushing, and then put them into a supercritical extraction kettle for supercritical extraction, using CO2 as the extraction agent, the ethanol entrainer concentration is 90%, the extraction pressure is 35MPa, the extraction temperature is 35°C, the extraction time is 3 hours, and 33g of ethanol plant compound extract is obtained after the extraction is completed;
- Step 2 Add 33.0g ethanol plant compound extract to the reaction vessel, add 1.5g L-hydroxyproline, react at 60°C for 6 hours, after the reaction, add 1.9g 3-chloro-2-hydroxypropyl Trimethyl ammonium chloride was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K3.
- Embodiment 1-3 is detected according to QB/T 2738-2012 "the evaluation method of antibacterial and antibacterial effect of daily chemical products ", section 7.2 suspension quantitative method to Candida albicans antibacterial property, the result is as follows:
- the bactericidal rate of the natural plant-modified antibacterial liquid with a concentration of 1% and 0.5% is both > 90%, which has a good bactericidal effect.
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- Zoology (AREA)
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- Agronomy & Crop Science (AREA)
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- General Chemical & Material Sciences (AREA)
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Abstract
A method for preparing a modified antifungal liquid from natural plants and a product thereof. By means of modifying an antifungal liquid extracted from natural plants, a composite antifungal liquid with a good fungicidal property is obtained. The process is simple. The obtained modified antifungal liquid is green and environmentally friendly, and has little stimulation and a wide application field.
Description
本发明属于抗菌剂领域,具体涉及一种天然植物改性抗菌液的制备方法及其产品。The invention belongs to the field of antibacterial agents, and in particular relates to a preparation method of a natural plant modified antibacterial liquid and a product thereof.
开发绿色安全的抗菌剂一直备受人们的关注。传统的化学合成抗菌剂尽管抗菌效果显著,但使用安全性及潜在的致病风险还有待进一步的评估及优化,特别是在食品接触和化妆品领域,为此人们对天然界植物的抗菌性进行了大量研究。天然的抗菌剂组分大多通过对植物进行乙醇提取浓缩,对人体的刺激性小,但达到相同抗菌效果的有效用量大大高于化学合成的抗菌剂,如何提升天然植物抗菌剂的抗菌性能同时又不影响安全性减少刺激性是当前植物抗菌剂发展的重要方向。The development of green and safe antibacterial agents has always attracted people's attention. Although traditional chemically synthesized antibacterial agents have remarkable antibacterial effects, their safety and potential risk of causing disease still need to be further evaluated and optimized, especially in the fields of food contact and cosmetics. For this reason, the antibacterial properties of natural plants have been studied Researching widely. Most of the natural antibacterial agent components are extracted and concentrated by ethanol from plants, which are less irritating to the human body, but the effective dosage to achieve the same antibacterial effect is much higher than that of chemically synthesized antibacterial agents. How to improve the antibacterial performance of natural plant antibacterial agents and at the same time Reducing irritation without affecting safety is an important direction for the development of plant antibacterial agents.
发明内容Contents of the invention
针对现有技术的不足,本发明目的在于提供一种天然植物改性抗菌液的制备方法。Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a preparation method of natural plant modified antibacterial liquid.
本发明的再一目的在于:提供一种根据上述方法制备的天然植物改性抗菌液产品。Another object of the present invention is to provide a natural plant modified antibacterial liquid product prepared according to the above method.
本发明目的通过如下方案实现:一种天然植物改性抗菌液的制备方法,其特征在于,包括以下步骤:The object of the present invention is realized by following scheme: a kind of preparation method of natural plant modified antibacterial liquid is characterized in that, comprises the following steps:
步骤一,按质量比为1:0.4~1.5:0.6~1.0将晒干的丁香花蕾、马齿笕全草和紫花地丁全草投入到粉碎机中进行粉碎,然后,加入到超临界萃取釜中进行超临界萃取,使用CO
2为萃取剂,乙醇溶液为夹带剂,萃取结束后得到乙醇植物复合提取液;
Step 1, according to the mass ratio of 1:0.4~1.5:0.6~1.0, put the dried clove flower buds, the whole plant of purslane and the whole plant of Viola chinensis into the pulverizer for crushing, and then add it to the supercritical extraction kettle Carry out supercritical extraction in the medium, use CO 2 as extractant, ethanol solution as entrainer, obtain ethanol plant composite extract after extraction is finished;
步骤二将步骤一中得到的乙醇植物复合提取液加入到反应容器中,加入L-羟基脯氨酸,L-羟基脯氨酸的用量为乙醇植物复合提取液总质量的1%-5%,在40℃-60℃下反应6小时,反应结束后,加入3-氯-2-羟丙基三甲基卤化铵改性剂回流12小时,3-氯-2-羟丙基三甲基卤化铵改性剂的摩尔用量与L-羟基脯氨酸摩尔用量的比为0.5~0.95:1,得到天然植物改性抗菌液。In step 2, the ethanol-plant composite extract obtained in step 1 is added to the reaction vessel, and L-hydroxyproline is added. The amount of L-hydroxyproline is 1%-5% of the total mass of the ethanol-plant composite extract. React at 40°C-60°C for 6 hours. After the reaction, add 3-chloro-2-hydroxypropyltrimethylammonium halide modifier and reflux for 12 hours. 3-chloro-2-hydroxypropyltrimethylammonium halide The ratio of the molar dosage of the ammonium modifier to the molar dosage of L-hydroxyproline is 0.5-0.95:1 to obtain the natural plant modified antibacterial liquid.
所述的天然植物改性抗菌液的制备方法,超临界萃取中,萃取压力为30- 40MPa,萃取温度为35℃-45℃,萃取时间为2-4小时。In the preparation method of the natural plant modified antibacterial liquid, in the supercritical extraction, the extraction pressure is 30-40MPa, the extraction temperature is 35°C-45°C, and the extraction time is 2-4 hours.
所述的天然植物改性抗菌液的制备方法,夹带剂乙醇溶液的浓度为85%-95%。In the preparation method of the natural plant modified antibacterial liquid, the concentration of the ethanol solution of the entrainer is 85%-95%.
本发明选择丁香花蕾、马齿笕全草和紫花地丁作为主要抗菌植物,丁香花蕾中含有丁香酚,具有植物芳香和明显的抗菌杀病毒作用,马齿笕含有黄酮化合物,具有抗过敏的功效,对大肠杆菌具有良好的抑制效果,紫花地丁提取物中黄酮甙类和有机酸对金色葡萄球菌的抑菌作用和杀菌作用最明显,本发明采用超临界萃取对三种植物进行提取,得到的乙醇植物复合提取液再与L-羟基脯氨酸进行反应,L-羟基脯氨酸为食品添加剂,分子结构中的羧基和羟基双官能团能够和乙醇植物复合提取液中的羟基和羧酸等官能团发生接枝反应得到含有仲胺基团的接枝化合物,接枝后的仲胺化合物与含卤素的改性剂改性,可形成阳离子季铵盐,进一步提高复合提取液的杀菌抗菌性能。本发明加入L-羟基脯氨酸的优势在于,L-羟基脯氨酸作为食品风味剂,安全性高,与乙醇植物复合提取液接枝后,仲胺基团可以和改性剂的卤素官能团发生取代反应,羧酸基团可以和改性剂的羟基基团发生反应,可以大大提高3-氯-2-羟丙基三甲基卤化铵阳离子醚化剂的接枝效果,大幅提升天然植物萃取液的杀菌效果,同时改性后的产品刺激性小,安全性高,可作为日化品、洗剂产品和工业涂料的杀菌剂使用,应用领域广泛。The present invention selects lilac flower buds, whole herb of purslane and viola as main antibacterial plants, lilac buds contain eugenol, which has plant aroma and obvious antibacterial and virus-killing effects, and purslane contains flavonoid compounds, which have antiallergic effects , has a good inhibitory effect on Escherichia coli, and the flavonoid glycosides and organic acids in the Viola extract have the most obvious antibacterial and bactericidal effects on Staphylococcus aureus. The present invention uses supercritical extraction to extract the three plants to obtain The ethanol plant compound extract is then reacted with L-hydroxyproline. L-hydroxyproline is a food additive. The carboxyl and hydroxyl bifunctional groups in the molecular structure can be combined with the hydroxyl and carboxylic acid in the ethanol plant compound extract. The grafted compound containing secondary amine groups is obtained through the grafting reaction of the functional groups. The grafted secondary amine compound is modified with a halogen-containing modifier to form a cationic quaternary ammonium salt, which further improves the bactericidal and antibacterial properties of the composite extract. The advantage of adding L-hydroxyproline in the present invention is that L-hydroxyproline is used as a food flavoring agent, which has high safety. After grafting with the ethanol plant compound extract, the secondary amino group can be combined with the halogen functional group of the modifier. A substitution reaction occurs, and the carboxylic acid group can react with the hydroxyl group of the modifier, which can greatly improve the grafting effect of the 3-chloro-2-hydroxypropyltrimethylammonium halide cationic etherification agent, and greatly improve the natural plant The bactericidal effect of the extract, and the modified product has low irritation and high safety. It can be used as a bactericide for daily chemicals, lotion products and industrial coatings, and has a wide range of applications.
本发明通过对萃取的天然植物的抗菌液进行改性,得到杀菌性能良好且安全性高的复合抗菌液,工艺简单,得到的改性抗菌液绿色环保刺激小,应用领域广泛。The invention modifies the extracted natural plant antibacterial liquid to obtain a compound antibacterial liquid with good bactericidal performance and high safety, the process is simple, the obtained modified antibacterial liquid has little environmental stimulation and wide application fields.
以下实施例是对本发明专利的进一步说明,但不对本发明专利造成任何限制。The following examples are further descriptions of the patent of the present invention, but do not cause any limitation to the patent of the present invention.
实施例1Example 1
一种天然植物改性抗菌液,按以下步骤制备:A kind of natural plant modified antibacterial liquid, prepared according to the following steps:
步骤一,将晒干的50g丁香花蕾、40g马齿笕全草和30g紫花地丁全草投入到粉碎机中进行粉碎,然后,加入到超临界萃取釜中进行超临界萃取,使用CO
2为萃取剂,乙醇夹带剂浓度为95%,萃取压力为35MPa,萃取温度为45℃, 萃取时间为2小时,萃取结束后得到28g乙醇植物复合提取液;
Step 1, put dried 50g clove flower buds, 40g whole plant of purslane dentata and 30g whole plant of Viola chinensis into a pulverizer for pulverization, then add them into a supercritical extraction kettle for supercritical extraction, using CO2 for The extraction agent, the ethanol entrainer concentration is 95%, the extraction pressure is 35MPa, the extraction temperature is 45°C, the extraction time is 2 hours, and 28g of ethanol plant compound extract is obtained after the extraction is completed;
步骤二,将步骤一中得到的28g乙醇植物复合提取液加入到反应容器中,加入0.8g L-羟基脯氨酸,在60℃下反应6小时,反应结束后,加入0.9g的3-氯-2-羟丙基三甲基卤化铵改性剂回流12小时,得到天然植物改性抗菌液K1。Step 2: Add 28g of the ethanol plant compound extract obtained in Step 1 into the reaction vessel, add 0.8g of L-hydroxyproline, and react at 60°C for 6 hours. After the reaction, add 0.9g of 3-chloro -2-Hydroxypropyltrimethylammonium halide modifier was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K1.
杀菌效果优异,见表1。Excellent bactericidal effect, see Table 1.
实施例2Example 2
一种天然植物改性抗菌液,按以下步骤制备:A kind of natural plant modified antibacterial liquid, prepared according to the following steps:
步骤一,将晒干的50g丁香花蕾、60g马齿笕全草和40g紫花地丁全草投入到粉碎机中进行粉碎,然后加入到超临界萃取釜中进行超临界萃取,使用CO
2为萃取剂,乙醇夹带剂浓度为85%,萃取压力为35MPa,萃取温度为40℃,萃取时间为2.5小时,萃取结束后得到40g乙醇植物复合提取液;
Step 1, put 50g of dried lilac flower buds, 60g of whole plant of purslane dentata and 40g of whole plant of Viola chinensis into a pulverizer for crushing, and then put them into a supercritical extraction kettle for supercritical extraction, using CO2 as the extraction agent, the ethanol entrainer concentration is 85%, the extraction pressure is 35MPa, the extraction temperature is 40°C, the extraction time is 2.5 hours, and 40g of ethanol plant compound extract is obtained after the extraction is completed;
步骤二,将40.0g乙醇植物复合提取液加入到反应容器中,加入1.1g L-羟基脯氨酸,在60℃下反应6小时,反应结束后,加入1.2g 3-氯-2-羟丙基三甲基氯化铵回流12小时,得到天然植物改性抗菌液K2。Step 2: Add 40.0g of ethanol plant compound extract to the reaction vessel, add 1.1g of L-hydroxyproline, and react at 60°C for 6 hours. After the reaction, add 1.2g of 3-chloro-2-hydroxypropyl Trimethyl ammonium chloride was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K2.
杀菌效果优异,见表1。Excellent bactericidal effect, see Table 1.
实施例3Example 3
一种天然植物改性抗菌液,按以下步骤制备:A kind of natural plant modified antibacterial liquid, prepared according to the following steps:
步骤一,将晒干的40g丁香花蕾、60g马齿笕全草和40g紫花地丁全草投入到粉碎机中进行粉碎,然后加入到超临界萃取釜中进行超临界萃取,使用CO
2为萃取剂,乙醇夹带剂浓度为90%,萃取压力为35MPa,萃取温度为35℃,萃取时间为3小时,萃取结束后得到33g乙醇植物复合提取液;
Step 1, put 40g of dried lilac flower buds, 60g of whole plant of purslane dentata and 40g of whole plant of Viola chinensis into a pulverizer for crushing, and then put them into a supercritical extraction kettle for supercritical extraction, using CO2 as the extraction agent, the ethanol entrainer concentration is 90%, the extraction pressure is 35MPa, the extraction temperature is 35°C, the extraction time is 3 hours, and 33g of ethanol plant compound extract is obtained after the extraction is completed;
步骤二,将33.0g乙醇植物复合提取液加入到反应容器中,加入1.5g L-羟基脯氨酸,在60℃下反应6小时,反应结束后,加入1.9g 3-氯-2-羟丙基三甲基氯化铵回流12小时,得到天然植物改性抗菌液K3。Step 2: Add 33.0g ethanol plant compound extract to the reaction vessel, add 1.5g L-hydroxyproline, react at 60°C for 6 hours, after the reaction, add 1.9g 3-chloro-2-hydroxypropyl Trimethyl ammonium chloride was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K3.
杀菌效果优异,见表1。Excellent bactericidal effect, see Table 1.
性能检测:Performance testing:
对实施例1-3按照QB/T 2738-2012《日化产品抗菌抑菌效果的评价方法》中7.2节悬液定量法对白色念珠菌抗菌性能进行检测,结果如下所示:Embodiment 1-3 is detected according to QB/T 2738-2012 " the evaluation method of antibacterial and antibacterial effect of daily chemical products ", section 7.2 suspension quantitative method to Candida albicans antibacterial property, the result is as follows:
从结果可以看出,使用1%和0.5%浓度的天然植物改性抗菌液的杀菌率均>90%,具有良好的杀菌效果。It can be seen from the results that the bactericidal rate of the natural plant-modified antibacterial liquid with a concentration of 1% and 0.5% is both > 90%, which has a good bactericidal effect.
Claims (7)
- 一种天然植物改性抗菌液的制备方法,其特征在于,包括以下步骤:A preparation method of natural plant modified antibacterial liquid, is characterized in that, comprises the following steps:步骤一,按质量比为1:0.4~1.5:0.6~1.0将晒干的丁香花蕾、马齿笕全草和紫花地丁全草投入到粉碎机中进行粉碎,然后,加入到超临界萃取釜中进行超临界萃取,使用CO 2为萃取剂,乙醇溶液为夹带剂,萃取结束后得到乙醇植物复合提取液; Step 1, according to the mass ratio of 1:0.4~1.5:0.6~1.0, put the dried clove flower buds, the whole plant of purslane and the whole plant of Viola chinensis into the pulverizer for crushing, and then add it to the supercritical extraction kettle Carry out supercritical extraction in the medium, use CO 2 as extractant, ethanol solution as entrainer, obtain ethanol plant composite extract after extraction is finished;步骤二将步骤一中得到的乙醇植物复合提取液加入到反应容器中,加入L-羟基脯氨酸,L-羟基脯氨酸的用量为乙醇植物复合提取液总质量的1%-5%,在40℃-60℃下反应6小时,反应结束后,加入3-氯-2-羟丙基三甲基卤化铵改性剂回流12小时,3-氯-2-羟丙基三甲基卤化铵改性剂的摩尔用量与L-羟基脯氨酸摩尔用量的比为0.5~0.95:1,得到天然植物改性抗菌液。In step 2, the ethanol-plant composite extract obtained in step 1 is added to the reaction vessel, and L-hydroxyproline is added. The amount of L-hydroxyproline is 1%-5% of the total mass of the ethanol-plant composite extract. React at 40°C-60°C for 6 hours. After the reaction, add 3-chloro-2-hydroxypropyltrimethylammonium halide modifier and reflux for 12 hours. 3-chloro-2-hydroxypropyltrimethylammonium halide The ratio of the molar dosage of the ammonium modifier to the molar dosage of L-hydroxyproline is 0.5-0.95:1 to obtain the natural plant modified antibacterial liquid.
- 根据权利要求1所述的天然植物改性抗菌液的制备方法,其特征在于,超临界萃取中,萃取压力为30-40MPa,萃取温度为35℃-45℃,萃取时间为2-4小时。The preparation method of natural plant modified antibacterial liquid according to claim 1, characterized in that, in supercritical extraction, the extraction pressure is 30-40MPa, the extraction temperature is 35°C-45°C, and the extraction time is 2-4 hours.
- 根据权利要求1所述的天然植物改性抗菌液的制备方法,其特征在于,夹带剂乙醇溶液的浓度为85%-95%。The preparation method of natural plant modified antibacterial liquid according to claim 1, characterized in that the concentration of entrainer ethanol solution is 85%-95%.
- 根据权利要求1至3任一项所述的天然植物改性抗菌液的制备方法,其特征在于,按以下步骤制备:According to the preparation method of the natural plant modified antibacterial liquid described in any one of claims 1 to 3, it is characterized in that, prepared according to the following steps:步骤一,将晒干的50g丁香花蕾、40g马齿笕全草和30g紫花地丁全草投入到粉碎机中进行粉碎,然后,加入到超临界萃取釜中进行超临界萃取,使用CO 2为萃取剂,乙醇夹带剂浓度为95%,萃取压力为35MPa,萃取温度为45℃,萃取时间为2小时,萃取结束后得到28g乙醇植物复合提取液; Step 1, put dried 50g clove flower buds, 40g whole plant of purslane dentata and 30g whole plant of Viola chinensis into a pulverizer for pulverization, then add them into a supercritical extraction kettle for supercritical extraction, using CO2 for The extraction agent, the ethanol entrainer concentration is 95%, the extraction pressure is 35MPa, the extraction temperature is 45°C, the extraction time is 2 hours, and 28g of ethanol plant compound extract is obtained after the extraction is completed;步骤二,将步骤一中得到的28g乙醇植物复合提取液加入到反应容器中,加入0.8g L-羟基脯氨酸,在60℃下反应6小时,反应结束后,加入0.9g的3-氯-2-羟丙基三甲基卤化铵改性剂回流12小时,得到天然植物改性抗菌液K1。Step 2: Add 28g of the ethanol plant compound extract obtained in Step 1 into the reaction vessel, add 0.8g of L-hydroxyproline, and react at 60°C for 6 hours. After the reaction, add 0.9g of 3-chloro -2-Hydroxypropyltrimethylammonium halide modifier was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K1.
- 根据权利要求1至3任一项所述的天然植物改性抗菌液的制备方法,其特征在于,按以下步骤制备:According to the preparation method of the natural plant modified antibacterial liquid described in any one of claims 1 to 3, it is characterized in that, prepared according to the following steps:步骤一,将晒干的50g丁香花蕾、60g马齿笕全草和40g紫花地丁全草投入到粉碎机中进行粉碎,然后加入到超临界萃取釜中进行超临界萃取,使用CO 2 为萃取剂,乙醇夹带剂浓度为85%,萃取压力为35MPa,萃取温度为40℃,萃取时间为2.5小时,萃取结束后得到40g乙醇植物复合提取液; Step 1, put 50g of dried lilac flower buds, 60g of whole plant of purslane dentata and 40g of whole plant of Viola chinensis into a pulverizer for crushing, and then put them into a supercritical extraction kettle for supercritical extraction, using CO2 as the extraction agent, the ethanol entrainer concentration is 85%, the extraction pressure is 35MPa, the extraction temperature is 40°C, the extraction time is 2.5 hours, and 40g of ethanol plant compound extract is obtained after the extraction is completed;步骤二,将40.0g乙醇植物复合提取液加入到反应容器中,加入1.1g L-羟基脯氨酸,在60℃下反应6小时,反应结束后,加入1.2g 3-氯-2-羟丙基三甲基氯化铵回流12小时,得到天然植物改性抗菌液K2。Step 2: Add 40.0g of ethanol plant compound extract to the reaction vessel, add 1.1g of L-hydroxyproline, and react at 60°C for 6 hours. After the reaction, add 1.2g of 3-chloro-2-hydroxypropyl Trimethyl ammonium chloride was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K2.
- 根据权利要求1至3任一项所述的天然植物改性抗菌液的制备方法,其特征在于,按以下步骤制备:According to the preparation method of the natural plant modified antibacterial liquid described in any one of claims 1 to 3, it is characterized in that, prepared according to the following steps:步骤一,将晒干的40g丁香花蕾、60g马齿笕全草和40g紫花地丁全草投入到粉碎机中进行粉碎,然后加入到超临界萃取釜中进行超临界萃取,使用CO 2为萃取剂,乙醇夹带剂浓度为90%,萃取压力为35MPa,萃取温度为35℃,萃取时间为3小时,萃取结束后得到33g乙醇植物复合提取液; Step 1, put 40g of dried lilac flower buds, 60g of whole plant of purslane dentata and 40g of whole plant of Viola chinensis into a pulverizer for crushing, and then put them into a supercritical extraction kettle for supercritical extraction, using CO2 as the extraction agent, the ethanol entrainer concentration is 90%, the extraction pressure is 35MPa, the extraction temperature is 35°C, the extraction time is 3 hours, and 33g of ethanol plant compound extract is obtained after the extraction is completed;步骤二,将33.0g乙醇植物复合提取液加入到反应容器中,加入1.5g L-羟基脯氨酸,在60℃下反应6小时,反应结束后,加入1.9g 3-氯-2-羟丙基三甲基氯化铵回流12小时,得到天然植物改性抗菌液K3。Step 2: Add 33.0g ethanol plant compound extract to the reaction vessel, add 1.5g L-hydroxyproline, react at 60°C for 6 hours, after the reaction, add 1.9g 3-chloro-2-hydroxypropyl Trimethyl ammonium chloride was refluxed for 12 hours to obtain natural plant modified antibacterial liquid K3.
- 一种天然植物改性抗菌液,其特征在于根据权利要求1-6任一所述方法制备得到。A natural plant modified antibacterial liquid, characterized in that it is prepared according to any one of claims 1-6.
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CN117530369A (en) * | 2023-12-26 | 2024-02-09 | 山东晟迅康生物科技有限公司 | Easily-absorbed feed additive and preparation method thereof |
CN117530369B (en) * | 2023-12-26 | 2024-04-12 | 山东晟迅康生物科技有限公司 | Easily-absorbed feed additive and preparation method thereof |
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