CN107920976A - 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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- CN107920976A CN107920976A CN201680046624.4A CN201680046624A CN107920976A CN 107920976 A CN107920976 A CN 107920976A CN 201680046624 A CN201680046624 A CN 201680046624A CN 107920976 A CN107920976 A CN 107920976A
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- lactams
- biosurfactant
- rhamnolipid
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- 239000003876 biosurfactant Substances 0.000 claims abstract description 24
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
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- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- 229910052794 bromium Inorganic materials 0.000 claims description 2
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- 241000894006 Bacteria Species 0.000 abstract description 4
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- -1 heterocyclic radical Chemical class 0.000 description 11
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- 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
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- 206010011224 Cough Diseases 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
- 229920002306 Glycocalyx Polymers 0.000 description 1
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- 102000004895 Lipoproteins Human genes 0.000 description 1
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- 239000004909 Moisturizer Substances 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
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- HIWPGCMGAMJNRG-ACCAVRKYSA-N Sophorose Natural products O([C@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HIWPGCMGAMJNRG-ACCAVRKYSA-N 0.000 description 1
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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
- A01N25/30—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
- 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
- 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
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
包含内酰胺和生物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
本申请要求于2015年8月20日提交的EP 15181851.5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生物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生物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。组合物还包含内酰胺和生物表面活性剂。
例如,在第一方面,本发明涉及组合物,其包含内酰胺和生物表面活性剂,其中所述内酰胺是具有式(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是苯基或取代苯基,例如单取代苯基。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,其包含内酰胺和生物表面活性剂,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任何家庭护理组合物(机构的、组织的或消费者家庭的)或个人护理组合物(例如护肤霜或浆液(serum)),或者工业组合物(例如抗生物膜涂料或漆,例如用于海上环境)。组合物也可以是农业化学品。组合物可以适用于用作抗微生物组合物。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%,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%的内酰胺。
生物表面活性剂优选地包含微生物来源的生物表面活性剂。优选地,其包含糖脂生物表面活性剂部分,所述糖脂生物表面活性剂部分可以是鼠李糖脂或槐糖脂或海藻糖脂(trehalolipid)或甘露糖赤藓糖醇脂(MEL)或其组合。
替代性地或另外地,生物表面活性剂可以包含任何剪切稀化生物表面活性剂,并且在这方面可以延伸至包含任何剪切稀化的上述糖脂生物表面活性剂,或者任何剪切稀化的纤维二糖、肽基的生物表面活性剂、脂蛋白、脂肽(例如表面活性肽)、脂肪酸(例如corynomucolic酸(优选地具有烃链C12-C14))、磷脂(例如由在正烷烃上生长的红串红球菌产生的磷脂酰乙醇胺,导致水和十六烷之间的界面张力降低至小于1mN m-1且CMC为30mg L-1(Kretschner等,1982))、刺孢青霉酸(spiculisporic acid)、聚合物生物表面活性剂(包括emulsan、liposan、甘露糖蛋白或多糖-蛋白质复合物)或其组合。
优选地,生物表面活性剂是鼠李糖脂或槐糖脂。
优选地,生物表面活性剂部分包含鼠李糖脂。
生物表面活性剂部分可以包含一个或多个糖部分,例如糖环。在鼠李糖脂的情况下,鼠李糖脂可以包含一种组分或组分两者:具有单一鼠李糖糖环的单鼠李糖脂和具有两个鼠李糖糖环的二鼠李糖脂。
在鼠李糖脂的情况下,在整个本专利说明书中,前缀单-和二-分别用于表示单鼠李糖脂(具有单一鼠李糖糖环)和二鼠李糖脂(具有两个鼠李糖糖环)。如果使用缩写,R1是单鼠李糖脂并且R2是二鼠李糖脂。
槐糖脂包含疏水性脂肪酸尾和亲水性碳水化合物槐糖(sophotose)头。脂肪酸尾可以是饱和的或不饱和的。槐糖脂是本领域已知的。
内酰胺与生物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。
生物表面活性剂可用于替代组合物中总表面活性剂的至少50重量%。
优选地生物表面活性剂以总表面活性剂的20-90重量%的水平存在,更优选地生物表面活性剂以总表面活性剂的50-80重量%存在,且更优选地总表面活性剂的50-75重量%。
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。
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、清洁剂或浆液)。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
使用以下方法,使用超临界CO2,从由提供的JBR425的商业样品提取和纯化单鼠李糖脂和二鼠李糖脂。
将JBR425(来自)的商业样品与Celllite 载体混合并转移到超临界CO2提取器。增加温度和压力以产生超临界CO2,并且在脱脂步骤中从提取器移除残留的油和脂肪。然后在超临界CO2存在下将助溶剂(工业甲基化溶剂(IMS))加入到Cellite 载体上的剩余脱脂鼠李糖脂混合物中。以2.5%至10%的递增梯度引入助溶剂IMS以促进不同单鼠李糖脂和二鼠李糖脂比率的分离和移除。
制备以下结果中所示的水平的生物表面活性剂溶液以用于筛选。测试的最高水平取决于表面活性剂在水中的溶解度。以下代表性实施例使用4-(4-氯苯基)-5-亚甲基-吡咯-2-酮。
将固体内酰胺称量到配有0.45μm尼龙过滤器的Mini Uniprep样品小瓶中滤(每小瓶2.7至3.3mg)。将50μL的溶剂溶液放入每个样品小瓶中,给小瓶盖上盖子并用手轻轻振摇以摇动固体,然后放置于Thermo Labsystems平板摇床上并连续摇动48小时。此后,使用整体式滤过膜去除小瓶中的过量固体,并通过HPLC分析所得溶液以测定溶解的内酰胺的水平。
使用配有Hypersil Gold C18柱(15×2.1×3μm)的Agilent系列HPLC,使用流速为0.4mL/min的60/40甲醇/水(+0.1%甲酸)等度洗脱,使用DAD检测器在285nm分析样品。4-(4-氯苯基)-5-亚甲基-吡咯-2-酮的保留时间为约2.8分钟。
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对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。
发明人已经证实鼠李糖脂生物表面活性剂有益于增加水中的内酰胺溶解度,特别是在较低浓度下。最好的实施例是R2。
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 (7)
1.一种组合物,其包含内酰胺和生物表面活性剂,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.权利要求1所述的组合物,其中R是H、F、Cl、Br或Me。
3.前述权利要求中任一项所述的组合物,其中所述内酰胺选自:
4.前述权利要求中任一项所述的组合物,其中所述生物表面活性剂是鼠李糖脂。
5.权利要求1至3中任一项所述的组合物,其中所述生物表面活性剂是二鼠李糖脂。
6.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至多20-90重量%的生物表面活性剂。
7.权利要求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。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101410372A (zh) * | 2006-01-24 | 2009-04-15 | 拜欧希格诺有限公司 | 新内酰胺类 |
WO2014118240A1 (en) * | 2013-02-01 | 2014-08-07 | Unilever Plc | Antimicrobial composition comprising a lactam and a hydrotrope |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2207031A1 (en) | 1994-12-06 | 1996-06-13 | The Procter & Gamble Company | Shelf stable skin cleansing liquid with gel forming polymer, lipid and crystalline ethylene glycol fatty acid ester |
BR9610945A (pt) | 1995-09-18 | 1999-07-13 | Procter & Gamble | Sistema de distribuição de alta eficiência compreendendo zeólitos |
AU2002950862A0 (en) | 2002-08-19 | 2002-09-12 | Biosignal Pty Ltd | Furanone derivatives and methods of making same |
US20070269473A1 (en) | 2004-04-27 | 2007-11-22 | Micap Plc | Microbial Encapsulation |
US20130142855A1 (en) * | 2004-12-22 | 2013-06-06 | Polytechnic Institute Of New York University | Modified sophorolipids combinations as antimicrobial agents |
GB0502790D0 (en) | 2005-02-10 | 2005-03-16 | Univ London Pharmacy | Solid dispersion of hydrophobic bioactive |
US20070006951A1 (en) * | 2005-07-07 | 2007-01-11 | Wade Summers | Ventilated tires |
WO2008013899A2 (en) * | 2006-07-27 | 2008-01-31 | Aurora Advance Beauty Labs | Rhamnolipid-based formulations |
US20100038816A1 (en) | 2006-08-16 | 2010-02-18 | Novartis Ag | Method of making solid dispersions of highly crystalline therapeutic compounds |
US20090175810A1 (en) | 2008-01-03 | 2009-07-09 | Gareth Winckle | Compositions and methods for treating diseases of the nail |
JP2011510006A (ja) | 2008-01-16 | 2011-03-31 | ダウ グローバル テクノロジーズ エルエルシー | 界面重合によるカプセル化疎水性活性物質 |
BRPI0922586A2 (pt) | 2008-12-18 | 2016-07-26 | Unilever Nv | composição detergente para lavagem de tecidos, processo para a lavagem de tecidos, e, processo para a fabricação da referida composição |
US8592381B2 (en) * | 2008-12-18 | 2013-11-26 | Rhamnopharma Inc. | Method for treating rhinitis and sinusitis by rhamnolipids |
US10226405B2 (en) | 2009-09-18 | 2019-03-12 | International Flavors & Fragrances Inc. | Purified polyurea capsules, methods of preparation, and products containing the same |
US11311467B2 (en) | 2009-09-18 | 2022-04-26 | International Flavors & Fragrances Inc. | Polyurea capsules prepared with a polyisocyanate and cross-linking agent |
RU2013134339A (ru) | 2010-12-23 | 2015-01-27 | Эбботт Гмбх Унд Ко. Кг | Твердые составы с замедленным действием на основе твердой дисперсии |
BR112013028716A2 (pt) | 2011-05-13 | 2017-01-24 | Unilever Nv | detergente de lavanderia líquido concentrado aquoso, composição, método de lavagem de tecidos de poliéster e seu uso |
US20140294925A1 (en) * | 2013-03-08 | 2014-10-02 | AGAE Technologies LLC | Formulations combining ramoplanin and rhamnolipids for combating bacterial infection |
DE102013218134A1 (de) | 2013-09-11 | 2015-03-12 | Evonik Industries Ag | Beschichtungsmittel enthaltend Polysiloxan-Quats |
CN108024938A (zh) | 2015-08-20 | 2018-05-11 | 荷兰联合利华有限公司 | 改善的内酰胺溶解度 |
WO2017029112A1 (en) | 2015-08-20 | 2017-02-23 | Unilever Plc | Lactam compositions |
-
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101410372A (zh) * | 2006-01-24 | 2009-04-15 | 拜欧希格诺有限公司 | 新内酰胺类 |
WO2014118240A1 (en) * | 2013-02-01 | 2014-08-07 | Unilever Plc | Antimicrobial composition comprising a lactam and a hydrotrope |
Non-Patent Citations (1)
Title |
---|
林晖 等: ""不同组分鼠李糖脂的胶束性质及其对三氯生的增溶作用"", 《环境科学学报》 * |
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