JP7432089B2 - 高効率抗菌性ヒドロキシ酸エステルオリゴマー - Google Patents
高効率抗菌性ヒドロキシ酸エステルオリゴマー Download PDFInfo
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- JP7432089B2 JP7432089B2 JP2021175005A JP2021175005A JP7432089B2 JP 7432089 B2 JP7432089 B2 JP 7432089B2 JP 2021175005 A JP2021175005 A JP 2021175005A JP 2021175005 A JP2021175005 A JP 2021175005A JP 7432089 B2 JP7432089 B2 JP 7432089B2
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- antibacterial
- ester
- acid ester
- hydroxy acid
- ester oligomer
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- 230000000844 anti-bacterial effect Effects 0.000 title claims description 19
- -1 hydroxy acid ester Chemical class 0.000 title description 8
- 239000000126 substance Substances 0.000 claims description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- OMSUIQOIVADKIM-RXMQYKEDSA-N ethyl (R)-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@@H](C)O OMSUIQOIVADKIM-RXMQYKEDSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- KDPXOGYCOOUWOS-MRVPVSSYSA-N hexyl (2R)-2-hydroxypropanoate Chemical compound CCCCCCOC(=O)[C@@H](C)O KDPXOGYCOOUWOS-MRVPVSSYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WHBMMWSBFZVSSR-GSVOUGTGSA-N (R)-3-hydroxybutyric acid Chemical compound C[C@@H](O)CC(O)=O WHBMMWSBFZVSSR-GSVOUGTGSA-N 0.000 description 5
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 5
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 5
- NUOMIZNYSYMUJI-SECBINFHSA-N Hexyl (R)-3-hydroxybutyrate Chemical compound CCCCCCOC(=O)C[C@@H](C)O NUOMIZNYSYMUJI-SECBINFHSA-N 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- OMSUIQOIVADKIM-UHFFFAOYSA-N ethyl 3-hydroxybutyrate Chemical compound CCOC(=O)CC(C)O OMSUIQOIVADKIM-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 239000004599 antimicrobial Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 241001360526 Escherichia coli ATCC 25922 Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- LHDWRKCOQQHAMP-SSDOTTSWSA-N butyl (3r)-3-hydroxybutanoate Chemical compound CCCCOC(=O)C[C@@H](C)O LHDWRKCOQQHAMP-SSDOTTSWSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- YSYUKRFFRSRBMO-SNVBAGLBSA-N heptyl (3R)-3-hydroxybutanoate Chemical compound CCCCCCCOC(C[C@@H](C)O)=O YSYUKRFFRSRBMO-SNVBAGLBSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- OCJMVWOGIMJYNT-LLVKDONJSA-N octyl (3R)-3-hydroxybutanoate Chemical compound CCCCCCCCOC(C[C@@H](C)O)=O OCJMVWOGIMJYNT-LLVKDONJSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- GNYIQDNGLKBFCP-MRVPVSSYSA-N pentyl (3R)-3-hydroxybutanoate Chemical compound CCCCCOC(=O)C[C@@H](C)O GNYIQDNGLKBFCP-MRVPVSSYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 206010011409 Cross infection Diseases 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- LDLDJEAVRNAEBW-UHFFFAOYSA-N Methyl 3-hydroxybutyrate Chemical compound COC(=O)CC(C)O LDLDJEAVRNAEBW-UHFFFAOYSA-N 0.000 description 1
- 206010029803 Nosocomial infection Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 210000002390 cell membrane structure Anatomy 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- KWWOQRSLYPHAMK-UHFFFAOYSA-N ethyl 2-hydroxybutanoate Chemical compound CCOC(=O)C(O)CC KWWOQRSLYPHAMK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PZSYRGVIJCBHDE-SECBINFHSA-N heptyl (2R)-2-hydroxypropanoate Chemical compound CCCCCCCOC(=O)[C@@H](C)O PZSYRGVIJCBHDE-SECBINFHSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- LDLDJEAVRNAEBW-SCSAIBSYSA-N methyl (3r)-3-hydroxybutanoate Chemical compound COC(=O)C[C@@H](C)O LDLDJEAVRNAEBW-SCSAIBSYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000070 poly-3-hydroxybutyrate Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- DYIMQAHDHMHISM-ZCFIWIBFSA-N propyl (3r)-3-hydroxybutanoate Chemical compound CCCOC(=O)C[C@@H](C)O DYIMQAHDHMHISM-ZCFIWIBFSA-N 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Images
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/68—Lactic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Description
1、本発明は、分子構造の設計に注目して、式(I)で表される物質の末端基及び鎖長の構造を合理的に設計するとともに、そのclogP値を制御することにより、本発明の式(I)で表される物質のサイズを適切にし、式(I)で表される物質が細菌の内部への浸透能力及び細菌の細胞膜に対する破壊能力の両方を最大限に向上させることで、効率的な抗菌という目的を達成させる。
2、本発明は、分子構造を正確に設計することでR-(-)-ヒドロキシ酸エステルオリゴマーの親水性と疎水性を調整し、水溶性制御可能なバイオベースの抗菌剤を得、その使用範囲を広げ、例えば、食品、医薬品や化粧品などの分野では、水溶性が高く、使用しやすく、水中の物質が均一に分散している抗菌剤が必要であり、水溶性ヒドロキシ酸エステルオリゴマーは、使用ニーズをよく満たすことができ、一方、塗料、繊維、プラスチックや建材などの分野では、抗菌効果を長持ちさせるために耐水性を有する抗菌剤が必要であり、この場合では、非水溶性のヒドロキシ酸エステルオリゴマーのみがこの要件を満たすことができる。
3、本発明で使用される原材料はすべて、バイオベースの原材料であり、便利で入手が容易であり、合成プロセス中に有毒な触媒及び溶媒の使用を避け、複雑な後処理を避け、且つ触媒をリサイクルすることができ、スケールアップと生産が容易であり、環境保護要件を満たし、生産コストを削減するのにも役立つ。
Claims (1)
Priority Applications (1)
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JP2023136426A JP2023165680A (ja) | 2020-10-26 | 2023-08-24 | 高効率抗菌性ヒドロキシ酸エステルオリゴマー |
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CN202011155869.5 | 2020-10-26 | ||
CN202011155869.5A CN112359071A (zh) | 2020-10-26 | 2020-10-26 | 一种水溶性可控抗菌物质及合成工艺 |
CN202111137059.1 | 2021-09-27 | ||
CN202111137059.1A CN113913474A (zh) | 2020-10-26 | 2021-09-27 | 一种高效抗菌的羟基酸酯低聚物 |
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JP2023136426A Division JP2023165680A (ja) | 2020-10-26 | 2023-08-24 | 高効率抗菌性ヒドロキシ酸エステルオリゴマー |
Publications (2)
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JP2022070249A JP2022070249A (ja) | 2022-05-12 |
JP7432089B2 true JP7432089B2 (ja) | 2024-02-16 |
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JP2021175005A Active JP7432089B2 (ja) | 2020-10-26 | 2021-10-26 | 高効率抗菌性ヒドロキシ酸エステルオリゴマー |
JP2023136426A Pending JP2023165680A (ja) | 2020-10-26 | 2023-08-24 | 高効率抗菌性ヒドロキシ酸エステルオリゴマー |
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JP2023136426A Pending JP2023165680A (ja) | 2020-10-26 | 2023-08-24 | 高効率抗菌性ヒドロキシ酸エステルオリゴマー |
Country Status (5)
Country | Link |
---|---|
US (2) | US20220110905A1 (ja) |
EP (2) | EP3988536A1 (ja) |
JP (2) | JP7432089B2 (ja) |
CN (3) | CN112359071A (ja) |
WO (1) | WO2022088286A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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CN112359071A (zh) * | 2020-10-26 | 2021-02-12 | 浙江英玛特生物科技有限公司 | 一种水溶性可控抗菌物质及合成工艺 |
CN115182161A (zh) * | 2022-07-08 | 2022-10-14 | 浙江英玛特生物科技有限公司 | 采用scf技术将羟基酸酯低聚物固着在纤维表面的方法及抗菌抗病毒产品 |
CN115323774A (zh) * | 2022-08-01 | 2022-11-11 | 浙江英玛特生物科技有限公司 | 基于饱和羟基酸酯低聚物scf体系的抗菌抗病毒纤维的制备方法及其产品 |
CN115627629A (zh) * | 2022-09-08 | 2023-01-20 | 浙江英玛特生物科技有限公司 | 利用羟基酸酯低聚物复配防污剂对渔网绳缆的防污加工方法及其产品 |
CN115652626A (zh) * | 2022-09-08 | 2023-01-31 | 浙江英玛特生物科技有限公司 | 基于scf技术的水溶性纤维抗菌化加工方法及其产品 |
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JP2022070249A (ja) | 2022-05-12 |
CN112359071A (zh) | 2021-02-12 |
EP4292590A3 (en) | 2024-03-13 |
US20240082201A1 (en) | 2024-03-14 |
JP2023165680A (ja) | 2023-11-16 |
CN116178159A (zh) | 2023-05-30 |
EP3988536A1 (en) | 2022-04-27 |
CN113913474A (zh) | 2022-01-11 |
EP4292590A2 (en) | 2023-12-20 |
WO2022088286A1 (zh) | 2022-05-05 |
US20220110905A1 (en) | 2022-04-14 |
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