CN116983220A - 改善的内酰胺溶解度 - Google Patents
改善的内酰胺溶解度 Download PDFInfo
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- CN116983220A CN116983220A CN202311169175.0A CN202311169175A CN116983220A CN 116983220 A CN116983220 A CN 116983220A CN 202311169175 A CN202311169175 A CN 202311169175A CN 116983220 A CN116983220 A CN 116983220A
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- nonionic surfactant
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- 150000003951 lactams Chemical class 0.000 title claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 94
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 44
- 239000000194 fatty acid Substances 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- -1 ethyleneoxy groups Chemical group 0.000 claims description 6
- 125000005313 fatty acid group Chemical group 0.000 claims description 2
- 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
- 125000000217 alkyl group Chemical group 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
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- 239000000654 additive Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
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- 230000000996 additive effect Effects 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
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- 239000007787 solid Substances 0.000 description 5
- 229920001213 Polysorbate 20 Polymers 0.000 description 4
- 229920001219 Polysorbate 40 Polymers 0.000 description 4
- 125000003147 glycosyl group Chemical group 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
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- 239000008103 glucose Substances 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
- 229950008882 polysorbate Drugs 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 2
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 2
- 229940068977 polysorbate 20 Drugs 0.000 description 2
- 229940101027 polysorbate 40 Drugs 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 125000001424 substituent group Chemical group 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
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
- 239000004677 Nylon Substances 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- OURRXQUGYQRVML-AREMUKBSSA-N [4-[(2s)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate Chemical compound CC1=CC(C)=CC=C1C(=O)OCC1=CC=C([C@@H](CN)C(=O)NC=2C=C3C=CN=CC3=CC=2)C=C1 OURRXQUGYQRVML-AREMUKBSSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000032770 biofilm formation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000003221 ear drop Substances 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
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 239000003752 hydrotrope Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 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
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
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- 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
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- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005406 washing Methods 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
- 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
- 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
- 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
- A01N25/30—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 characterised by the surfactants
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
Abstract
包含内酰胺和非离子表面活性剂的组合物,适用于用作抗微生物、抗生物膜和抑菌组合物。
Description
本案是本申请人于2016年7月28日提交的申请号为201680047398.1、题为“改善的内酰胺溶解度”的专利申请的分案申请,该母案的全部内容通过引用并入本分案。
本申请要求于2015年8月20日提交的EP 15181858.0的优先权,其出于所有目的通过引用并入本文。
技术领域
本发明涉及包含内酰胺和非离子表面活性剂的组合物。组合物适合用作例如抗微生物、抗生物膜和抑菌组合物。
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。
然而,这些内酰胺的使用受限于与某些制剂的相容性,特别是在某些水溶液中的溶解度。
发明内容
本发明涉及包含内酰胺和非离子表面活性剂的组合物。发明人已经惊奇地发现非离子表面活性剂的存在有利地改善了内酰胺的溶解度。
更具体地,本发明涉及如WO 2007/085042和WO 2004/016588中所述的包含内酰胺的组合物,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。组合物还包含非离子表面活性剂。
例如,在第一方面,本发明涉及组合物,其包含内酰胺和非离子表面活性剂,其中所述内酰胺是具有式(I)或(II)的内酰胺:
(I)或(II)/>
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,本发明可以提供组合物,其包含内酰胺和非离子表面活性剂,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,内酰胺是具有式Ia的内酰胺。在一些实施方式中,内酰胺是具有式IIa的内酰胺。
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)。
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。
合适地,组合物是水性组合物。它可以是非水性组合物。
优选地,组合物含有0.000001至50重量%内酰胺,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%。
在一些情况下,非离子表面活性剂可以是聚山梨醇酯(换句话说,用脂肪酸酯化的聚乙二醇化失水山梨糖醇)。聚山梨醇酯是可商购的并且通常被称为聚山梨醇酯XX或XX,其中XX表示PEG单位的总数量。
合适的聚山梨醇酯可以包括聚山梨醇酯20(聚氧乙烯(20)失水山梨糖醇单月桂酸酯),聚山梨醇酯40(聚氧乙烯(20)失水山梨糖醇单棕榈酸酯),聚山梨醇酯60(聚氧乙烯(20)失水山梨糖醇单硬脂酸酯),聚山梨醇酯80(聚氧乙烯(20)失水山梨糖醇单油酸酯)。优选的非离子表面活性剂可以包括20。
在一些情况下,非离子表面活性剂可以是脂肪酸烷氧基化物,例如乙氧基化物。脂肪酸烷氧基化物可以具有C8-35烷基或烯基链,优选C10-18烷基或烯基链,最优选C10-18烷基链,例如C10-12烷基链或C12-15烷基链。应理解,烷基和烯基链可以是支链或直链。脂肪酸乙氧基化物可以具有例如3至25,更优选5至15个亚乙基氧基基团,例如表面活性剂。优选的表面活性剂是具有7个亚乙基氧基基团的C12-15醇乙氧基化物。这可以被称为25-7。
换句话说,非离子表面活性剂可以是式(II)的脂肪酸乙氧基化物:
Alk-(OCH2)pOH (II)
其中p是3至25,优选5至15,更优选5至10,最优选7;
并且Alk是C8-35烷基或烯基链,优选C10-15烷基链,例如C10-15烷基链,例如C12-15烷基链。
组合物可以包含至多20重量%,例如至多15重量%的非离子表面活性剂。合适地,非离子表面活性剂的量是组合物的至多10重量%。例如,组合物可以包含0.01至10重量%,例如0.1至10重量%,任选地1至10重量%的表面活性剂。在一些情况下,非离子表面活性剂的量可以是至多9重量%,8重量%,7重量%,6重量%,5重量%,4重量%,3重量%或甚至至多2重量%。如本文所证明的,可以使用非常少量的表面活性剂而仍然提供增强的溶解度。例如,量可以小于2重量%,例如小于1.5重量%,小于1重量%,并且在一些情况下低至0.5重量%。
内酰胺与非离子表面活性剂的比率可以例如是1:0.5至1:20,优选1:0.5至1:10,例如1:0.5至1:5。
本发明还包括下列项目:
1.一种组合物,其包含内酰胺和非离子表面活性剂,其中所述内酰胺是具有式Ia或式IIa的内酰胺:
其中R是H、卤素或C1-4烷基。
2.项目1所述的组合物,其中R是H、F、Cl、Br或Me。
3.前述项目中任一项所述的组合物,其中所述内酰胺选自:
4.前述项目中任一项所述的组合物,其中所述非离子表面活性剂是聚山梨醇酯,任选地其中所述聚山梨醇酯是20。
5.项目1至3中任一项所述的组合物,其中所述非离子表面活性剂是脂肪酸烷氧基化物,任选地其中所述非离子表面活性剂具有式(II)的结构:
Alk-(OCH2)pOH (II)
其中Alk是C8-35烷基或烯基链,且p是3至25。
6.项目5所述的组合物,其中所述非离子表面活性剂是具有7个亚乙基氧基基团的C12-15醇乙氧基化物;任选地其中所述非离子表面活性剂是25-7。
7.前述项目中任一项所述的组合物,其中所述组合物包含至多20重量%的非离子表面活性剂,任选地其中所述组合物包含小于2重量%的非离子表面活性剂。
8.项目1至6中任一项所述的组合物,其中内酰胺与非离子表面活性剂的比率为1:0.5至1:20。
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。
非离子表面活性剂
出于本公开的目的,除非另有说明,否则“非离子表面活性剂”应被定义为分子量小于约10,000的两亲性分子,其基本上不含在6-11的正常洗涤pH下表现出净电荷的任何官能团。
虽然在下文中进一步讨论优选材料,但是可以使用任何类型的非离子表面活性剂。高度优选的是脂肪酸烷氧基化物,特别是乙氧基化物,其具有C8-35烷基或烯基链,优选C8-30烷基或烯基链,更优选C10-24烷基或烯基链,特别是C10-18烷基或烯基链,烷基可以是优选的,并且具有优选3至25,更优选5至15个亚乙基氧基基团,例如可获自(海牙,荷兰)的/>表面活性剂;可以具有1,000至30,000分子量的环氧乙烷/环氧丙烷嵌段聚合物,例如来自BASF(Ludwigshafen,德国)的/>和烷基酚乙氧基化物,例如可获自Dow/>(Midland,Mich.,USA)的Triton/>
其他非离子表面活性剂可以是优选的。这些包括烷醇胺与脂肪酸的缩合物,例如椰油酰胺DEA,多元醇-脂肪酸酯,例如可获自(Gouda,荷兰)的Span系列,乙氧基化多元醇-脂肪酸酯,例如可获自Uniqema(Gouda,荷兰)的/>系列,烷基多葡糖苷,例如可获自/>(Düsseldorf,德国)的APG类,和正烷基吡咯烷酮,例如ISP(Wayne,N.J.,USA)销售的/>系列产品。
例如,非离子表面活性剂可以是包含酯化失水山梨糖醇的非离子表面活性剂,例如式(III)的非离子表面活性剂:
其中w+x+y+z是0至20,并且n是烷基或烯基。例如,w+x+y+z可以是0,如在可获自的Span系列中;并且Alk可以是C8-35,例如C10-24,特别是C10-18。例如,在Span单棕榈酸酯中,Alk是C15烷基,而在Span 20中,Alk是C11烷基。
例如,w+x+y+z可以是20,如在系列中,也被称为聚山梨醇酯。合适的聚山梨醇酯可以包括聚山梨醇酯20(聚氧乙烯(20)失水山梨糖醇单月桂酸酯),聚山梨醇酯40(聚氧乙烯(20)失水山梨糖醇单棕榈酸酯),聚山梨醇酯60(聚氧乙烯(20)失水山梨糖醇单硬脂酸酯),聚山梨醇酯80(聚氧乙烯(20)失水山梨糖醇单油酸酯)。
非离子表面活性剂可以是例如式IV的烷基多糖:
RO(CnH2nO)t(糖基)x(IV)
其中R选自烷基、烷基苯基、羟烷基、羟烷基苯基及其混合物,其中烷基含有约10至约18,优选约12至约14个碳原子;n是0至3,优选2;t是0至约10,优选0;并且x是1.3至约10,优选1.3至约2.7。糖基优选来源于葡萄糖。为了制备这些化合物,首先形成醇或烷基多乙氧基醇,然后与葡萄糖或葡萄糖源反应以形成葡糖苷(在1位连接)。然后可以将额外的糖基单元连接在它们的1-位与前面的糖基单元的2-、3-、4-和/或6-位(优选主要是2-位)之间。
此外,也可以使用上文没有具体提到的,但在定义范围内的非离子表面活性剂。
当然,应理解,可以使用多于一种非离子表面活性剂;换句话说,组合物可以包含多于一种如本文所述的非离子表面活性剂。在这种情况下,本文公开的非离子表面活性剂的量是指非离子表面活性剂的总量。
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。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
NIS的筛选
以下代表性实施例使用4-(4-氯苯基)-5-亚甲基-吡咯-2-酮。
将过量的固体内酰胺(约3mg)置于配有0.45μm尼龙过滤器的MiniUniprep样品小瓶中。加入水或水+添加剂(NIS)(500μL),摇晃混合物并短暂地轻敲以开始分散固体,然后使用配有小瓶支架的平板摇床摇动混合物48小时。48小时后,通过将具有整体式过滤器的柱塞在小瓶上向下按压,从系统中除去固体。这除去固体并在内室中提供过滤溶液,然后使其准备用于分析。
使用HPLC分析定量溶解在溶液中的内酰胺的水平。在配有Thermo HypersilC18柱(15×2.1×3μm)的Agilent/>系列HPLC上分析样品,用60/40的甲醇/水(+0.1%甲酸)等度洗脱,流速为0.4mL/min,在285nm处使用DAD检测器。测试的内酰胺具有约2.8分钟的保留时间。
对于每种添加剂,测量溶液中的内酰胺的绝对水平,并报告为相对于单独的水的内酰胺溶解度的增加。
一式三份测试每个测试表面活性剂溶液,并计算溶液中的内酰胺的平均值。溶解度值被引用作为相对于单独的水的水溶性的改善(即,溶解在水+溶剂中的内酰胺的平均水平/溶解在水中的内酰胺的平均水平)以允许在不同天数进行筛选之间的比较。
发明人已经证明,非离子表面活性剂有益于增加内酰胺在水中的溶解度,特别是在较低浓度下。最好的实例是20和/>25-7。
应理解的是,除非另有明确规定,否则所有的优选项是可以组合的。
Claims (5)
1.一种组合物,其包含内酰胺和0.5至2重量%的非离子表面活性剂,其中所述内酰胺是选自以下的内酰胺:
并且其中所述非离子表面活性剂是脂肪酸乙氧基化物,其中所述脂肪酸乙氧基化物是具有5至15个亚乙基氧基基团的C12-15醇乙氧基化物。
2.根据权利要求1所述的组合物,其中所述非离子表面活性剂是具有7个亚乙基氧基基团的C12-15醇乙氧基化物。
3.根据权利要求1所述的组合物,其中所述非离子表面活性剂是25-7。
4.根据前述权利要求中任一项所述的组合物,其中所述组合物包含小于2重量%的非离子表面活性剂。
5.根据权利要求1至3中任一项所述的组合物,其中内酰胺与非离子表面活性剂的比率为1:0.5至1:20。
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DE212014000038U1 (de) * | 2013-02-01 | 2015-09-21 | Unilever N.V. | Zusammensetzung |
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WO2017029071A1 (en) * | 2015-08-20 | 2017-02-23 | Unilever Plc | Dispersed lactams |
EP3337451B1 (en) * | 2015-08-20 | 2018-12-26 | Unilever PLC | Improved lactam solubility |
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- 2016-07-28 CN CN202311169175.0A patent/CN116983220A/zh active Pending
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2018
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WO2017029093A1 (en) | 2017-02-23 |
EP3337450B1 (en) | 2023-05-10 |
CN107920979A (zh) | 2018-04-17 |
BR112018003182A2 (pt) | 2018-09-25 |
US20180220643A1 (en) | 2018-08-09 |
EP3337450A1 (en) | 2018-06-27 |
US10888087B2 (en) | 2021-01-12 |
ZA201800840B (en) | 2019-07-31 |
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