CN108024939B - 包封的内酰胺 - Google Patents
包封的内酰胺 Download PDFInfo
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- CN108024939B CN108024939B CN201680047462.6A CN201680047462A CN108024939B CN 108024939 B CN108024939 B CN 108024939B CN 201680047462 A CN201680047462 A CN 201680047462A CN 108024939 B CN108024939 B CN 108024939B
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- lactam
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- carrier oil
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- 150000003951 lactams Chemical class 0.000 title claims abstract description 82
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000002199 base oil Substances 0.000 claims description 20
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 15
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 14
- 238000005538 encapsulation Methods 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000012985 polymerization agent Substances 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 6
- 230000003385 bacteriostatic effect Effects 0.000 abstract description 6
- 230000003214 anti-biofilm Effects 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- -1 monosubstituted phenyl Chemical group 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000012696 Interfacial polycondensation Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000002781 deodorant agent Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000002979 fabric softener Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- HHCPGPHTKXVNHA-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methylidenepyrrol-2-one Chemical compound C1=CC(Cl)=CC=C1C1=CC(=O)NC1=C HHCPGPHTKXVNHA-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000005188 oxoalkyl group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- IXQWYGLOOGNNNJ-UHFFFAOYSA-N 4-(4-bromophenyl)-5-hydroxy-5-methyl-1h-pyrrol-2-one Chemical compound CC1(O)NC(=O)C=C1C1=CC=C(Br)C=C1 IXQWYGLOOGNNNJ-UHFFFAOYSA-N 0.000 description 1
- PZRSWNREEOYEQO-UHFFFAOYSA-N 4-(4-fluorophenyl)-5-hydroxy-5-methyl-1h-pyrrol-2-one Chemical compound CC1(O)NC(=O)C=C1C1=CC=C(F)C=C1 PZRSWNREEOYEQO-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- FUKWTNWVVLHOQQ-UHFFFAOYSA-N 5-hydroxy-5-methyl-4-phenyl-1h-pyrrol-2-one Chemical compound CC1(O)NC(=O)C=C1C1=CC=CC=C1 FUKWTNWVVLHOQQ-UHFFFAOYSA-N 0.000 description 1
- YSZWLEFVAJQHJS-UHFFFAOYSA-N 5-methylidene-4-(4-methylphenyl)pyrrol-2-one Chemical compound C1=CC(C)=CC=C1C1=CC(=O)NC1=C YSZWLEFVAJQHJS-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000032770 biofilm formation Effects 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- 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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
-
- 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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/87—Polyurethanes
-
- 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
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Toxicology (AREA)
- Dermatology (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
适用于组合物的包封的内酰胺和包含包封的内酰胺的组合物。所述组合物可用作抗微生物、抗生物膜和抑菌组合物。包封内酰胺的方法。
Description
本申请要求于2015年8月20日提交的EP 15181842.4的优先权,其出于所有目的通过引用并入本文。
技术领域
本发明涉及包封的内酰胺。所述包封的内酰胺适用于组合物,例如抗微生物、抗生物膜和抑菌组合物。本发明还涉及包封内酰胺的方法。
背景技术
WO 2007/085042和WO 2004/016588公开了用于抗微生物益处的内酰胺和关于其合成的步骤。WO2014/118240公开了包含内酰胺和助水溶物的抗微生物组合物。US2011/0059144涉及通过将疏水性活性物质包封在聚脲壳中而改善个人护理组合物的美学的方法。
然而,这些内酰胺的使用受限于与某些制剂的相容性。
发明内容
本发明涉及包封的内酰胺。内酰胺的包封允许制剂的更大的灵活性,因为包封可以允许在更高pH的制剂中使用内酰胺和/或改善它们的溶解性。在一些情况下,包封有助于内酰胺的控制式和触发式释放。
更具体地,本发明涉及包封的内酰胺,如WO 2007/085042和WO 2004/016588中所述,其内容特别是其中明确说明的内酰胺结构通过引用并入本文。
例如,在第一方面,本发明涉及包封的式(I)或(II)的内酰胺:
其中:
R1和R2各自独立地选自氢、卤素、烷基、环烷基、烷氧基、氧代烷基、烯基、杂环基、杂芳基、芳基和芳烷基;和
R3选自氢、羟基、烷基、环烷基、烷氧基、氧代烷基、烯基、杂环基、杂芳基、环烷基、芳基、芳烷基和–C(O)CR6=CH2;
R4和R5独立地选自氢、芳基、杂环基、杂芳基和芳烷基;和
R6选自氢和甲基;和
R7选自氢和–C(O)CR6=CH2;和
优选地,R4和R5中的至少一个是氢。
应理解的是,在适当的情况下,基团可以任选地被取代。任选的取代基可以包括卤素、C1-4烷基、C1-4卤代烷基(例如CF3)和C1-4烷氧基。
烷基可以例如是C1-12烷基,例如C1-6烷基。芳基可以例如是C6-10芳基,例如苯基。
优选地,R1和R2中的至少一个选自杂环基、杂芳基、芳基和芳烷基。
优选地,R1是氢。优选地,R3是氢。优选地,R4是氢。优选地,R5是氢。优选地,R6是氢。优选地,R7是氢。优选地,R2是芳基或芳烷基。更优选地,R2是苯基或取代的苯基,例如单取代的苯基。取代可以是邻位、间位或对位。优选地,其是对位。优选的取代基包括卤素和甲基。例如但不限于,R2可以选自苯基、4-氟苯基、4-氯苯基、4-溴苯基和4-甲基苯基。
因此,在第一方面,本发明可以提供包封的内酰胺,其中所述内酰胺是具有式Ia或式IIa的内酰胺:
其中R是H、卤素(优选F、Cl或Br)或C1-4烷基(优选甲基)。
在一些实施方式中,包封的内酰胺是具有式Ia的内酰胺。在一些实施方式中,包封的内酰胺是具有式IIa的内酰胺。
重要的是,已经发现式Ia的内酰胺在高pH7条件下是不稳定的(高pH是指至少7的pH)。包封改善了在这些条件下的稳定性,允许内酰胺被用于更广泛的组合物。
优选的内酰胺可以包括:
4-(4-氯苯基)-5-亚甲基-吡咯-2-酮(Ref.488);
5-亚甲基-4-(对甲苯基)吡咯-2-酮(Ref.491);
4-苯基-5-羟基-5-甲基-1H-吡咯-2-酮(Ref.131);
4-(4-氟苯基)-5-羟基-5-甲基-1H-吡咯-2-酮(Ref.258);
4-(4-溴苯基)-5-羟基-5-甲基-1H-吡咯-2-酮(Ref.316)。
合适地,包封的内酰胺是聚合物包封的内酰胺。
包封的内酰胺可以被包封在选自聚脲聚合物、三聚氰胺-甲醛共聚物、脲甲醛共聚物及其混合物的聚合物中。
发明人已经惊奇地发现如本文所述的内酰胺抑制自由基聚合。
因此,合适地,聚合物是缩聚物。
例如,聚合物可以是由二胺和二异氰酸酯生成的缩聚物。
例如,聚合物可以是或可以包含式P1的聚脲:
其中RP1包含亚苯基且RP2是亚烷基。
例如,RP1可以是-CH2-亚苯基;换句话说,聚合物可以衍生自多亚甲基多苯基异氰酸酯。
例如,RP2可以是式-(CH2)m-的直链亚烷基。在一些情况下,m是2至10,例如2至8,例如4至8,例如6的整数(换句话说,RP2可以是亚己基)。
换句话说,内酰胺可以被包封在由多亚甲基多苯基异氰酸酯和1,6-己二胺形成的聚合物中。
在一些情况下,聚合物和/或包封物结构被选择和/或配置成允许控制式或触发式释放。例如,包封物可以在某些条件下以预定速率溶解。例如,包封物可以响应于触发因素而释放。触发因素可以是,例如,酸、碱、盐、酶的存在,或某个浓度的酸、碱、盐、酶;或非化学触发因素,如超声或光。
合适地,内酰胺被包封以形成平均直径为约10纳米至约1000微米,优选约50纳米至约100微米,更优选约2至约40微米,甚至更优选约4至15微米的颗粒。特别优选的范围是约5至10微米,例如6至7微米。包囊分布可以是窄的、宽的或多峰的。多峰分布可以由不同类型的包封化学构成。
包封过程合适地在载体油中完成,载体油可以是酮。例如,载体油可以是C5-20烷基酮,例如C5-15烷基酮,例如C5-10烷基酮,例如C6-8烷基酮,例如C7烷基酮。烷基酮可以是支链或直链。优选地,它是直链。烷基酮的氧代基团可位于C2处;换句话说,烷基酮可以是烷基-2-酮。优选的载体油是2-庚酮。
获得的在载体油中的包封的内酰胺可以用作用于组合物的添加剂。
因此,在第二方面,本发明涉及包含包封的内酰胺的添加剂。合适地,包封的内酰胺被提供在载体油中。内酰胺可以是式I或式II的内酰胺。
因此,在第二方面,本发明可以提供包含包封的内酰胺的添加剂,其中所述内酰胺是在载体油中的式Ia或式IIa的内酰胺(其中R如本文所定义)。
优选的内酰胺可以如第一方面所述。
在一些实施方式中,载体油是如上所述的烷基酮。优选它是C5-10烷基-2-酮,最优选它是庚-2-酮。
包封的内酰胺适用于组合物。组合物可以是但不限于个人护理组合物、家庭护理组合物、药物组合物或工业组合物(例如抗生物膜涂料或漆,例如用于海上环境)中的任一种。组合物也可以是农业化学品。组合物可以适合用作抗微生物、抗生物膜和抑菌组合物。本文提供了这样的组合物的非限制性实例。组合物也可以用作添加剂组合物;换句话说,组合物可以与另外的成分(例如赋形剂)组合以形成如上所述的组合物。
因此,本发明的第三方面涉及包含包封的内酰胺的组合物。内酰胺可以是式I或式II的内酰胺。
因此,在第三方面,本发明可以提供包含包封的式Ia或IIa的内酰胺(其中R如本文所定义)的组合物。
优选的内酰胺可以如第一方面所述。
有利地,组合物可以是pH≥7,例如≥8,例如≥9,例如≥10,例如≥11的组合物。
优选地,组合物含有0.000001至50重量%,更优选0.001至50重量%。甚至更优选0.01至5重量%,最优选0.01至2重量%的内酰胺。
在第四方面,本发明涉及包封内酰胺的方法,所述方法包括界面缩聚。内酰胺可以是式I或式II的内酰胺,并且下文描述的选项和优选项可以应用。
因此,在第四方面,本发明可以提供包封式Ia或IIb的内酰胺(其中R如本文所述)的方法,所述方法包括:
(a)将所述内酰胺与载体油合并;然后
(b)将在载体油中的所述内酰胺与第一聚合剂合并;然后
(c)将步骤(b)的产物与稳定剂的水溶液合并;
(d)在搅拌所述混合物的同时将包含第二聚合剂的水溶液加入到步骤(c)的产物中;
其中所述第一聚合剂和第二聚合剂当它们彼此反应时形成聚合物。
应理解,载体油和水溶液是不可混溶的。因此聚合是界面缩聚。
第一聚合剂可以是异氰酸酯。例如,它可以是多亚甲基多苯基异氰酸酯。第二聚合剂可以是二胺,例如C2-10亚烷基α,ω-二胺(α,ω-diamino C2-10alkylene),如1,6-己二胺。
合适地,内酰胺被溶解在载体油中。上文描述了优选的载体油。换句话说,步骤(a)的产品是溶液。合适地,溶液的浓度为约0.5重量%。它可以更高。例如,它可以是约1重量%。在一些情况下,溶液的浓度小于5重量%,合适地小于3重量%。
合适地,步骤(c)包括剧烈搅动,例如均化。速度可以大于5k rpm,例如大于10krpm。它可以是大约15k rpm。合适地,步骤(c)的产物是乳液(即,混合物可以被乳化)。
合适地,步骤(d)包括搅动,例如以至多1000rpm,至多500rpm。它可以是200-300rpm。步骤(d)可以持续大约1小时。
方法可以包括固化步骤(步骤(e))。例如,步骤(e)可以包括将步骤(d)的产物搅动1小时,2小时,3小时,4小时,5小时。搅动可以使用瓶式滚筒。
稳定剂可以是磺酸盐,例如萘磺酸盐,如烷基萘磺酸盐缩合物(NSC)。可商购实例是可获自/>(Surface Chemistry)。
应理解,关于第一方面描述的选项和优选项在可能的情况下同样适用于其他方面,反之亦然。
附图说明
图1显示使用界面缩聚方法的包封的简单代表。
图2显示固化的包含根据本发明的包封的内酰胺的乳液。
图3显示根据本发明的包封的颗粒的显微镜照片。
具体实施方式
内酰胺可以使用在WO 2007/085042和WO 2004/016588中所述的方法获得,其全部内容通过引用并入本文。
组合物
本文所述的组合物可以是具有抗微生物活性的组合物。在一些情况下,组合物是抗菌的。它们可以具有杀菌和/或抑菌活性。发明人已经观察到期望的抑菌活性。因此,在一些情况下,组合物是抑菌组合物。
组合物还可以预防和/或抑制生物膜的形成。当微生物粘附到表面时,形成生物膜。可以形成生物膜细胞外聚合物质。生物膜(也被称为粘泥(slime))在工业环境中带来问题;例如它们可以形成在装置的管道中,或工业和农业结构中、太阳能电池板上、以及船体和其他船舶结构上。生物膜也可以在家庭环境中造成问题。例如,生物膜可以在家用电器例如洗衣机中形成。生物膜也存在于个人护理中,例如它们可以形成在牙齿表面上。
适用于任何和所有这些应用的组合物都在本发明的范围内。在一些情况下,组合物是漆或其他涂料。在这样的情况下,组合物还可以包含粘结剂,任选地颜料和任选地一种或多种常规添加剂(例如,以改变表面张力、改善流动性、改善成品外观、增加湿边、改善颜料稳定性等——这样的添加剂是本领域已知的)。组合物可以包含水性溶剂或有机溶剂以适应目的。
组合物还可以用于医疗应用,例如用于涂覆包括医疗装置的设备。
在一些情况下,组合物是药物组合物。换句话说,组合物可以包含如本文所述的内酰胺和药学上可接受的赋形剂。组合物可适用于局部使用(例如它可以是霜剂或洗剂),它可适用于眼部使用(例如它可以用作药物滴眼剂),它可适用于耳朵使用(例如它可以用作滴耳剂),它可适用作漱口剂,或它可适用于口服施用。
在一些情况下,组合物是适用于家庭(通常被称为家庭护理组合物)或机构的组合物。家庭护理组合物包括但不限于清洁产品、洗衣洗涤剂和织物调理剂。在一些情况下,组合物是家庭护理组合物,例如洗衣液。因此组合物可以包含洗涤表面活性剂和助洗剂。组合物可以是织物调理剂(也被称为织物柔顺剂)并且可以包含抗静电剂。组合物也可以是家庭清洁产品。
在一些情况下,组合物是个人护理组合物。例如,组合物可以旨在用于皮肤上(例如霜剂、清洁剂或精华液(serum))。例如,组合物可用于痤疮的预防和治疗。例如,组合物可以包含聚二甲基硅氧烷、凡士林、保湿剂(例如透明质酸或甘油)和神经酰胺中的一种或多种。组合物可以是除臭/止汗组合物。在一些情况下,组合物是包含洗涤剂的个人护理组合物,例如,组合物可以是洗脸或沐浴凝胶或洗发香波。组合物可以是除香波以外的毛发处理组合物。组合物可以是除臭组合物(例如,除臭粉末、糊剂或液体)。组合物可以是口腔护理组合物(例如牙膏或漱口水),并且可以包含例如氟化物和/或调味剂。
在一些情况下,组合物是隐形眼镜清洁液。
组合物可以是适用于农业的组合物,例如作为土壤添加剂(固体或液体)。
组合物可以是适用于玻璃或透镜的处理或制造的组合物,例如作为用于太阳能电池板的添加剂/处理剂。
实施例
以下合成作为说明和示例提供,而非作为限制。
包封通过界面缩聚方法实现,其可被如图1所示简单地代表。
以下代表性实施例使用4-(4-氯苯基)-5-亚甲基-吡咯-2-酮。
2-庚酮被用作内酰胺的载体(油相),比率为1:199(内酰胺:庚酮),其相当于0.5%内酰胺溶液。发明人已经确定内酰胺也可以以1%溶解。异氰酸酯是多亚甲基多苯基异氰酸酯(Mn340),并且交联剂是1,6-己二胺(HMDA)。乳化在15K的剪切下进行。稳定剂是被称为的商业萘磺酸盐。Morwet形成深棕色溶液,所以包封的浆液通常为浅黄色/棕色。
PU包封程序
油相A的制备:将5g(2-庚酮:内酰胺;1:199)和0.42g异氰酸酯(PMDI,340)在28ml小瓶中混合并搅动至完全溶解。
水相B的制备:在烧杯中制备含有3重量%的MorwetD425的16ml水。
胺溶液C的制备:制备HMDA水溶液(40%)。
将相B在15k rpm匀化下加入相A中,然后将混合物乳化2分钟(得到浅黄色乳液)。之后,在1分钟内将1ml溶液C逐滴加入到乳液中,同时在200-300rpm下搅拌。1小时后,将样品浆液放置在瓶式滚筒上大约5小时以获得图2所示的固化乳液。
从图3可以看出,获得了包封的颗粒。
应理解,除非另有明确规定,否则所有的优选项是可以组合的。
Claims (14)
1.一种包封的内酰胺,其中所述内酰胺选自:
其特征在于包封的内酰胺被包封在缩聚物中,其中所述缩聚物由异氰酸酯和C2-10亚烷基α,ω-二胺形成;并且所述内酰胺被溶解在载体油中,其中所述载体油是庚-2-酮。
2.根据权利要求1所述的包封的内酰胺,其中所述内酰胺被包封在由多亚甲基多苯基异氰酸酯和1,6-己二胺形成的聚合物中。
3.一种添加剂,其包含在载体油中的根据权利要求1-2中任一项所述的包封的内酰胺,其中所述载体油是庚-2-酮。
4.一种组合物,其包含根据权利要求1至2中任一项所述的包封的内酰胺。
5.根据权利要求4所述的组合物,其中所述组合物含有0.000001至50重量%的内酰胺。
6.根据权利要求4所述的组合物,其中所述组合物含有0.001至50重量%的内酰胺。
7.根据权利要求4所述的组合物,其中所述组合物含有0.01至5重量%的内酰胺。
8.根据权利要求4所述的组合物,其中所述组合物含有0.01至2重量%的内酰胺。
9.一种包封内酰胺的方法,其中所述方法是缩聚物包封,其中所述内酰胺选自:
所述方法包括:
(a)将所述内酰胺与载体油合并,其中所述载体油是庚-2-酮;然后
(b)将在所述载体油中的所述内酰胺与第一聚合剂合并,其中所述第一聚合剂是异氰酸酯;然后
(c)将步骤(b)的产物与稳定剂的水溶液合并;
(d)在搅拌所述混合物的同时将包含第二聚合剂的水溶液加入到步骤(c)的产物中,其中所述第二聚合剂是C2-10亚烷基α,ω-二胺;
其中所述第一聚合剂和第二聚合剂当它们彼此反应时形成所述缩聚物。
10.根据权利要求9所述的方法,其中步骤(a)包括将所述内酰胺溶解在所述载体油中以形成溶液,其中所述溶液的浓度小于1重量%。
11.根据权利要求9或10所述的方法,其中所述第一聚合剂是多亚甲基多苯基异氰酸酯。
12.根据权利要求9或10所述的方法,其中所述第二聚合剂是1,6-己二胺。
13.根据权利要求9或10所述的方法,其中所述方法还包括搅拌步骤(d)的产物至少1小时的步骤。
14.根据权利要求9或10所述的方法,其中所述方法还包括搅拌步骤(d)的产物达5小时的步骤。
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- 2016-07-25 WO PCT/EP2016/067613 patent/WO2017029070A1/en active Application Filing
- 2016-07-25 US US15/750,893 patent/US20180228151A1/en not_active Abandoned
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2018
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ZA201800842B (en) | 2019-07-31 |
US20180228151A1 (en) | 2018-08-16 |
WO2017029070A1 (en) | 2017-02-23 |
US10918107B2 (en) | 2021-02-16 |
EP3337452A1 (en) | 2018-06-27 |
BR112018003173A2 (pt) | 2018-12-04 |
BR112018003173B1 (pt) | 2021-12-14 |
CN108024939A (zh) | 2018-05-11 |
EP3337452B1 (en) | 2024-03-27 |
US20200128826A1 (en) | 2020-04-30 |
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