CN1921822A - 烷氧基苯基羧酸衍生物 - Google Patents
烷氧基苯基羧酸衍生物 Download PDFInfo
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- CN1921822A CN1921822A CNA2005800055075A CN200580005507A CN1921822A CN 1921822 A CN1921822 A CN 1921822A CN A2005800055075 A CNA2005800055075 A CN A2005800055075A CN 200580005507 A CN200580005507 A CN 200580005507A CN 1921822 A CN1921822 A CN 1921822A
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Images
Classifications
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- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- 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
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
Abstract
式(I)的化合物在表面的抗菌处理,化妆品、家用产品、纺织和塑料的防腐,消毒剂使用中的用途,其中R1是取代或未取代的C1-C30烷基或者是取代或未取代的C3-C7环烷基,和R2是H、COOH或者是取代或未取代的O-C1-C30烷基。
Description
本发明涉及烷氧基苯甲酸衍生物在表面的抗菌处理(antimicrobialtreatment)中的应用,在化妆品、家用产品、纺织品和塑料制品的防腐(preservation)中的应用,以及在消毒剂(disinfectants)中的应用。
本发明涉及式(I)化合物在表面的抗菌处理上的应用,
其中
R1是取代或未取代的C1-C30烷基或者是取代或未取代的C3-C7环烷基,和
R2是H、COOH或者是取代或未取代的O-C1-C30烷基。
优选使用本发明的式(I)化合物,其中
R1是取代或未取代的C1-C20烷基或者是取代或未取代的C3-C7环烷基,和
R2是H、COOH或取代或未取代的O-C1-C20烷基。
特别优选使用本发明的式(I)化合物,其中
R1是取代或未取代的C8-C20烷基,和
R2是H、COOH或取代或未取代的O-C8-C20烷基;以及
非常特别优选使用本发明的式(I)化合物,其中
R1是取代或未取代的C8-C20烷基,和
R2是H或COOH。
C1-C30烷基、C1-C20烷基、C8-C20烷基、O-C1-C30烷基、O-C1-C20烷基和O-C8-C20烷基是直链的或支链,并且是未隔断的或被选自烃基和杂原子:-CR3=CR4-和O、S、CO、N、NR5中的至少一种隔断一次或多次的,
其中R3、R4和R5各自独立地是氢或C1-C4烷基。
例如,被O隔断的烷基是:
-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH3,或
-CH2CH2-O-CH2CH3,或-CH2CH2-O-CH2CH2-O-CH2CH2-O-CH2CH3,或
-CH2CH2-O-CH2CH2-CH2CH2-O-CH-(CH3)2。
例如,被N隔断的烷基是:
-CH2CH2CH2CH2CH2CH2CH2CH2-N(CH3)2、
-CH2CH2CH2CH2CHCH2-NH-CH3、-(CH2)7-N(CH3)-CH3、-(CH2)7-NH-CH3、
-CH2CH2CH2CH2-NH-CH2CH2CH2CH3或
-CH2CH2CH2CH2-N(CH3)-CH2CH2CH2CH3。
C1-C30烷基、C1-C20烷基、C8-C20烷基、O-C1-C30烷基、O-C1-C20烷基和-O-C8-C20烷基的取代基是例如,C1-C4烷基、卤化物或CN。
C1-C30烷基是例如,甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、正己基、正庚基、正辛基、1,1′,3,3′-四甲基丁基、2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基(eicosanyl)或三十烷基(tricosanyl)。
C1-C20烷基是例如,甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2′-二甲基丙基、正己基、正庚基、正辛基、1,1′,3,3′-四甲基丁基、2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基或二十烷基。
C8-C20烷基是例如,正辛基、1,1′,3,3′-四甲基丁基、2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基或二十烷基。
C1-C4烷基是例如,甲基、乙基、正丙基、异丙基、正丁基、仲丁基或叔丁基。
-O-C1-C30烷基是例如,甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2′-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1′,3,3′-四甲基丁氧基、2-乙基己氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十三烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基、十八烷氧基、十九烷氧基、二十烷氧基或三十烷氧基。
O-C1-C20烷基是例如,甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2′-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1′,3,3′-四甲基丁氧基、2-乙基己氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十三烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基、十八烷氧基、十九烷氧基或二十烷氧基。
O-C8-C20烷基是例如,正辛氧基、1,1′,3,3′-四甲基丁氧基或2-乙基己氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十三烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基、十八烷氧基、十九烷氧基或二十烷氧基。
C3-C7环烷基是例如,环丙基、环丁基、环戊基、环己基或环庚基。
卤化物是例如,氟化物、溴化物、氯化物或碘化物,优选氯化物。
在本发明的应用中,非常特别优选的化合物的实例是式
和
本发明的烷氧基苯甲酸衍生物是根据本身已知的方法制备,通常如下制备:在合适的溶剂如乙醇、乙腈、二甲基甲酰胺或丙酮中,在有机碱或无机碱优选碳酸钾存在下,用适当的卤代烷烷基化羟基羧酸的羧酸酯(优选为甲酯),然后水解烷氧基羧酸酯形成游离酸:
本发明式(I)的烷氧基苯甲酸衍生物表现出显著的抗菌活性,特别是抑制革兰氏阳性菌和革兰氏阴性菌,还抑制皮肤菌群的细菌,另外抑制酵母菌和霉菌。因此,它们特别适于一般的消毒、除臭以及皮肤和粘膜且还有皮肤附属物(毛发)的抗菌处理,十分特别适于手和伤口的消毒。
因此,本发明式(I)的烷氧基苯甲酸衍生物适于在个人护理制品,例如香波、浴用添加剂(bath additives)、护发制品、液体和固体肥皂(基于合成的表面活性剂和饱和的和/或不饱和的脂肪酸的盐)、洗液和乳膏、除臭剂、其它水或醇溶液如皮肤的清洁液、湿润清洁布(mosit cleansing cloth)、油或粉中用作抗菌活性成分和防腐剂。
本发明涉及一种个人护理制品,包含至少一种式(I)的化合物以及化妆品可容许的(cosmetically tolerable)载体或辅助剂。
本发明还涉及式(I)的化合物在皮肤、口腔和其它粘膜、牙齿的表面和毛发的抗菌处理、除臭和杀菌上的用途。
本发明还涉及式(I)的化合物在表面的杀菌和除臭上的应用。
本发明的个人护理制品,包括:
a)基于制品总重量计的0.01-15%重量,优选为0.1-10%重量的式(I)化合物,和
b)化妆品可容许的辅助剂。
取决于个人护理制品的形式,除了式(I)的烷氧基苯甲酸衍生物,其还可以包含其它组分,例如掩蔽剂(sequestering agent)、着色剂、芳香油、增稠剂或固定剂(稠度调节剂)、润肤剂、UV吸收剂、皮肤保护剂、抗氧化剂、改善力学性质的添加剂如二羧酸和/或C14-C22脂肪酸的铝、锌、钙和镁盐,和任选的防腐剂。
本发明的个人护理制品可以配制成油包水或水包油乳液、醇的制剂或含醇的制剂、离子或非离子的两亲脂质的多泡分散液(vesicular dispersion)、凝胶、固体棒或气溶胶制剂。
在油包水或水包油的乳液的情况下,化妆品可容许的辅助剂优选包含5-50%的油相,5-20%的乳化剂和30-90%的水。油相可以含适于化妆品制剂的任何油,例如一种或多种烃油、蜡、天然油、硅油、脂肪酸酯或脂肪醇。优选的一元或多元-醇是乙醇、异丙醇、丙二醇、己二醇、甘油和山梨糖醇。
本发明的化妆品制剂用于多个方面。例如,特别考虑下列制剂:
-护肤剂,如片剂形式或液体皂、无皂洗涤剂或洗涤糊剂(washingpaste)形式的皮肤洗涤和清洁制剂,
-沐浴制剂,如液体(泡沫浴、乳、淋浴制剂)或固体沐浴制剂,如浴块和浴盐;
-护肤剂,如护肤乳液(skin emulsion)、多重乳液或护肤油(skin oil);
-化妆用个人护理制剂,如以日霜或粉霜(powder cream)、扑面粉(松散的或压实的)、胭脂或乳膏化妆品形式的面部化妆品;眼部护理制剂,如眼影制剂、睫毛膏、眼线膏、眼霜或定眼乳膏(eye-fix cream);唇部护理制剂,如唇膏、润唇膏(lip gloss)、唇线笔;指甲护理制剂,如指甲油、指甲油去除剂、指甲硬化剂或角质层去除剂(cuticleremover);
-个人卫生制剂(intimate hygiene preparation),例如个人卫生洗液或个人用喷雾剂;
-足部护理制剂,如足浴、足粉、足霜或足用香脂(foot balsam),特殊防臭剂和止汗剂或老茧去除制剂(callus-removing preparation);
-光防护制剂,如防晒乳、洗剂、乳膏或油,防晒霜(sunblock)或热带粉(tropical),预晒黑制剂或晒后制剂;
-皮肤晒黑制剂,如自晒黑霜;
-褪色制剂(depigmenting preparation),如漂白皮肤用的制剂或皮肤光亮制剂;
-驱虫剂,如驱虫油、洗剂、喷雾剂或棒;
-除臭剂,如除臭喷雾、泵送喷雾剂、除臭凝胶、棒或走珠;
-止汗剂,如止汗剂棒、霜或走珠;
-用于清洁和护理被玷污皮肤的制剂,如无皂洗涤剂(固体或液体),剥离或擦洗制剂或剥离掩模;
-化学品形式的脱毛剂(脱毛),如毛发去除粉,液体脱毛剂,乳膏或糊形式的脱毛剂,凝胶形式或气溶胶泡沫的脱毛剂;
-剃须制剂,如剃须皂、发泡剃须乳膏、非发泡剃须乳膏、泡沫和凝胶、用于干剃须的须前制剂,须后水或须后洗剂;
-香料制剂,如含香料(科隆香水(eau de Cologne)、化妆香水(eau detoilette)、香味香水(eau de parfum)、化妆香味(parfum de toilette)、香料),芳香油或香料乳膏;
-用于牙齿、假牙和口腔护理的制剂,如牙膏、凝胶牙膏、牙粉、漱口水浓缩液、抗牙斑漱口液、假牙清洁剂或假牙固定剂;
-化妆品头发处理制剂,如洗发剂和调理剂形式的头发洗涤制剂,护发制剂,如预处理制剂、生发油(hair tonics)、造型乳膏(stylingcream)、造型凝胶(styling gels)、润发脂(pomade)、发用漂洗剂、处理包、深入型头发处理剂,头发结构化制剂,如用于烫发(热烫、温烫、冷烫)的烫发制剂,头发拉直制剂,液体头发定型制剂,头发泡沫,头发喷雾,漂发剂,如过氧化氢溶液、光亮洗发剂、漂白乳膏、漂白粉末、漂白糊剂或油,暂时、半永久或永久染发剂,包含自氧化染料、或天然头发着色剂如指甲花染料或甘菊的制剂。抗菌肥皂,例如,具有下列组分:
0.01-5%重量的式(I)化合物
0.3-1%重量的二氧化钛
1-10%重量的硬脂酸,和
加至100%的皂坯(soap base),例如牛油脂肪酸和椰油脂肪酸的钠盐或甘油。
香波,例如具有下列组分:
0.01-5%重量的式(I)化合物
12.0%重量的月桂醇聚氧乙烯醚-2-硫酸钠(sodium laureth-2-sulfate)
4.0%重量的椰油酰氨基丙基甜菜碱
3.0%重量的NaCl,和
加至100%的水。
除臭剂,例如具有下列组分:
0.01-5%重量的式(I)化合物
60%重量的乙醇
0.3%重量的芳香油,和
加至100%的水。
本发明还涉及口腔组合物,包含基于组合物总重量计0.01-15%重量的式(I)化合物,和口腔可容许的辅助剂(orally tolerable adjuvant)。
口腔组合物的实施例:
10%重量的山梨糖醇
10%重量的甘油
15%重量的乙醇
15%重量的丙二醇
0.5%重量的月桂基硫酸钠
0.25%重量的甲基椰油基牛磺酸钠(sodium methylcocyl taurate)
0.25%重量的聚氧丙丙烯/聚氧乙烯嵌段共聚物
0.10%重量的薄荷调味剂
0.1-0.5%重量的式(I)化合物,和
加至100%的水。
本发明的口腔组合物可以是例如凝胶、糊剂、乳膏或水性制剂(漱口水)的形式。
本发明的口腔组合物还可以包含有效地抑制龋齿形成的释放氟离子的化合物,例如无机氟化盐如氟化钠、氟化钾、氟化铵或氟化钙,或有机氟化盐如氟化胺,其商品名为奥拉氟(Olafluor)。
本发明还涉及式(I)化合物在表面防腐中的应用。
本发明还涉及式(I)化合物在抗菌处理,特别是纺织纤维材料的防腐中的应用。这样的材料是天然和染色或印花的纤维材料,例如丝、羊毛、聚酰胺或聚氨酯,特别是所有种类的纤维素纤维材料。这样的纤维材料包括,例如天然纤维素纤维如棉、亚麻、黄麻和大麻,还有纤维素和再生纤维素。优选合适的纺织纤维材料是棉的那些。
本发明还涉及式(I)的化合物在塑料的抗菌处理中的应用,特别是在给予塑料抗菌性或保存塑料上应用,例如聚乙烯、聚丙烯、聚氨酯、聚酯、聚酰胺、聚碳酸酯、胶乳等。其应用领域例如是地板覆盖材料(floor covering)、塑料涂层、塑料容器和包装材料;厨房和浴室器具(例如,刷子、淋浴布;海绵,浴室防滑垫)、胶乳、过滤材料(空气和水过滤器)、医学领域使用的塑料制品,例如绷扎材料(dressing material)、注射器、导管等、所谓的“医疗器械”、手套和床垫。
本发明还涉及式(I)化合物在纸例如尿布、卫生巾、月经带(panty liner)和卫生和家庭区域所用的衣物的抗菌处理中的应用。
本发明还涉及式(I)的化合物在洗涤和清洁配制剂例如液体和粉末去污剂或软化剂的抗菌处理中的应用。
本发明还涉及式(I)的化合物在家用和用于硬表面清洁和消毒的通用目的的清洁剂的抗菌处理中的应用。
清洁剂,例如具有以下组分:
0.01-5% 式(I)的化合物
3.0% 辛醇4EO
1.3% 脂肪醇C8-C10多聚葡萄糖苷
3.0% 异丙醇
加至100% 水。
除了化妆品和家用产品的防腐,在保留和给予商业产品如淀粉或纤维素衍生物的印刷增稠剂、表面涂料和油漆的抗菌性中使用式(I)的化合物以及在工业生产过程如处理纸中把它们用作灭菌剂是有可能的,尤其是在处理纸的溶液中。
本发明还涉及式(I)的化合物在木材和皮革的抗菌处理、皮革的防腐和给予皮革抗菌性中应用。
本发明还涉及式(I)的化合物在使美容产品和家用产品免于细菌损害中的应用。
本发明还涉及式(I)化合物在抑制和消灭形成生物被膜的细菌中的非治疗性应用。
式(I)的化合物适于渗透有生命和无生命表面上的生物被膜(biofilm),防止细菌粘结至表面,而且任选地防止生物被膜进一步形成,分离所述生物被膜和/或抑制生物基体中形成微生物的生物被膜的进一步生长,或者杀死所述微生物。
通常认为“生物被膜”是活微生物和死微生物(特别是细菌)的聚集物,其与它们的细胞外聚合物物质(EPS基体)形式的它们的代谢物(例如多糖)一起粘附在有生命和无生命表面。通常相对于浮游生物细胞表现出明显的生长抑制或致死作用的抗菌物质的活性相对于生物被膜内有机化的微生物显著降低,例如原因是活性物质未充分地渗透进入生物基体中。
在本发明中,这特别涉及人牙齿和口腔粘膜上的生物被膜,其在口腔中的变性疾病(例如牙斑或牙周炎)的发展中具有重要作用,这是由于形成生物被膜的微生物或它们的代谢物的结果。
以下的实施例说明了本发明的,但不限制本发明。
实施例1:2-十二烷氧基-苯甲酸(II)的制备
在氮气气氛下,将40.2ml(312mmol)2-羟基苯甲酸甲酯置于含47.4g(343mmol)碳酸钾的乙腈中,加热回流1小时(白色悬浮液)。然后,加入89.8ml(374mmol)的十二烷基溴和5.2g(31mmol)的碘化钾后,回流下搅拌48小时。
为进行加工(working up),取出溶剂,无色油状固体残留物悬浮在水中,用乙醚振摇萃取。醚相用1N NaOH水溶液洗,Na2SO4干燥。抽取溶剂后,剩下油状-固体残留物,其用甲醇重结晶。
无色晶体,收率:48.1g(理论值的48%)。
对于酯的水解,48.1g(150mmol)的甲酯悬浮于含25.2g(450mmol)KOH的265ml水的溶液中,悬浮液加热回流10小时(无色溶液)。用300ml的水稀释后,混合物用6N HCl的酸化至pH1,分离出无色沉淀,洗涤并干燥。
无色结晶,收率:42.0g(理论值的91%)。
实施例2:5-十六烷氧基-间苯二酸(III)的制备
在氮气气氛下,将24.0g(114mmol)5-羟基-间苯二酸二甲酯和17.3g(125mmol)碳酸钾悬浮于375ml的乙腈中,在80℃下加热1小时。再加入34.8ml(114mmol)的十六烷基溴,在氮气气氛下于80℃搅拌24小时。为进行加工,反应混合物浓缩并过滤;向白色残留物中加入250ml水,用175ml乙醚振摇萃取3次。浓缩有机相后,产物保持足够纯度,用于进一步的反应。
无色固体,收率:44.4g(理论值的90%)。
为水解酯,将90.5g 5-十六烷氧基-间苯二酸二甲酯悬浮于含45.9gKOH的500ml水的溶液中,悬浮液加热回流14小时。向混合物中加入6N的HCl,同时其仍然加热,直到反应强烈酸化;混合物冷却再过滤。残留物用水彻底地洗几次,干燥。
无色固体,收率:62.6g(理论值的73%)。
实施例3:测定琼脂掺入试验(MIC试验)中的最小抑菌浓度(MIC)
培养基: 酪蛋白-大豆粉胨琼脂(Merck)
*Sabouraud 4%葡萄糖琼脂(Merck)
稀释培养基: 无菌0.85%NaCl溶液
试验生物体: 金黄色葡萄球菌(Staphylococcus aureus)ATCC 6853和9144
大肠埃希杆菌(Escherichia coli)ATCC 10536和NCTC 8196
绿浓杆菌(Pseudomonas aemginosa)ATCC 15442
*白念珠菌(Candida albicans)ATCC 10231
*黑曲霉素ATCC 6275
培育: 37℃下24小时
*28℃下3天
试验溶液: 在适合的溶剂中制得所有试验物质的1%母液,用无菌
稀释液尽可能地稀释,以便在琼脂中得到500ppm-10
ppm的最终浓度。
试验原理:
将0.3ml的特定稀释度阶段(stage)和15ml的蒸馏的液体营养培养基混
将0.3ml的特定稀释度阶段(stage)和15ml的蒸馏的液体营养培养基混合。营养基质凝固后,将0.85%NaCl溶液中适合的生物稀释度的10μl的试验菌株点式接种在琼脂培养基中;
金黄色葡萄球菌ATCC 6538 1∶100稀释度
大肠埃希杆菌ATCC 10536 1∶1000稀释度
绿脓杆菌ATCC 15442 1∶1000稀释度
白念珠菌ATCC 10231 1∶10稀释度
黑曲霉素ATCC 6275 1∶10稀释度
表1:
微生物 | 2-十二烷氧基-苯甲酸(II) | 5-十六烷氧基-间苯二酸(III) |
金黄色葡萄球菌ATCC 6538 | 31.25 | 24 |
金黄色葡萄球菌ATCC 9144 | 31.25 | 24 |
表皮葡萄球菌(Staphylococcus epidermidis)ATCC 12228 | 15.63 | 12 |
极小棒杆菌(Corynebacterium minutissimum)ATCC 23348 | 15.63 | 24 |
痤疮丙酸杆菌(Propionibacterium acnes)ATCC 6919(*) | 15.63 | 12 |
大肠埃希杆菌NCTC 8196 | >500 | >48 |
大肠埃希杆菌ATCC 10536 | >500 | >48 |
普通变形菌(Proteus vulgaris)ATCC 6896 | >500 | >48 |
肺炎杆菌(Klebsiella pneumoniae)ATCC 4352 | >500 | >48 |
猪霍乱沙门菌(Salmonella choleraesuis)ATCC 9184 | >500 | >48 |
绿浓杆菌ATCC 15442 | >500 | >48 |
白念珠菌ATCC 10231 | >500 | >48 |
黑曲霉素ATCC 6275 | >500 | >48 |
实施例4:在连续的稀释试验中测定抑制各种口腔生物的MIC
培养基: 具有氯高铁血红素(hemin)和甲萘醌(menadione)的巯基乙酸盐液
体培养基
用于牙龈卟啉单胞菌(P.gingivalis)和变黑普雷沃氏菌(P.
nigrescens)的含氯高铁血红素和甲萘醌的哥伦比亚液体培养基
稀释培养基: 合适的量的物质用移液管直接放在培养基上
试验生物体: 伴放线放线杆菌(Actinobacillus actinomycetemcomitans)ATCC
43718
格氏链球菌(Streptococcus gordonii)ATCC 10558
变异链球菌(Streptococcus mutans)ATCC 33402
粘放线菌(Actinomyces viscosus)ATCC 43146
具核梭杆菌多形亚种(Fusobacterium nucleatum subsp.
polymorphum)ATCC 10953
牙龈卟啉单胞菌(Porphyromonas gingivalis)ATCC 33277
变黑普雷沃氏菌(Prevotella nigrescens)ATCC 33563
培育: 于37℃厌氧下,7-10天,或者含10%CO2的有氧条件下24小时,
用于链球菌和伴放线放线杆菌
试验溶液: 使用所有试验物质的乙醇母液,含1500ppm(w/w)。
试验原理:
使用棉花-羊毛签(cotton-wool-tipped stick)把细菌从血液琼脂平皿中移出,在合适的培养基(McFarland 0.5)达到合适的O.D.;这样的溶液未稀释用于具核梭杆菌和变黑普雷沃氏菌,1∶20稀释的用于其它菌株。0.1ml的细菌培养物加入2ml的各活性物质溶液中,按照上述进行培育。
表2:
微生物 | 2-十二烷氧基-苯甲酸(II) | 5-十六烷氧基-间苯二酸(III) |
伴放线放线杆菌ATCC43718 | >15 | 15 |
格氏链球菌ATCC10558 | 15 | ≤0.94 |
变异链球菌ATCC33402 | 7.5 | 3.75 |
粘放线菌ATCC43146 | 1.88 | 1.88 |
具核梭杆菌多形亚种ATCC10953 | >15 | >15 |
牙龈卟啉单胞菌ATCC3277 | 7.5 | ≤0.94 |
变黑普雷沃氏菌ATCC33563 | >15 | >15 |
实施例5:
测定2-十二烷氧基-苯甲酸(II)和5-十六烷氧基-间苯二酸(III)对于羟基磷灰石的直接性(substantivity)和生长抑制作用的试验
原理:
羟基磷灰石盘(直径10mm)放置在综合性涎(综合性涎)(DeutscheZahnrztliche Zeitschrift DZZ 5/2002)中,于NaCl中漂洗,然后在含50和500ppm的试验物质(II)和(III)的乙醇溶液中培育。然后,将盘引入Nunclon表面滴定平板(12孔),并在Caso养分培养基中于37℃培育24小时,Caso养分培养基已用粘性放线菌ATCC 43146(约105/ml)接种
结果:
图1和图2显示了,与未处理过的对照相比,吸附在用人造唾液预处理的羟基磷灰石盘上的2-十二烷氧基-苯甲酸(II)和5-十六烷氧基-间苯二酸(III)抑制了粘性放线菌的生长。
实施例6:
测试2-十二烷氧基-苯甲酸(II)在生物被膜模型中的活性
原理:参见Guggenheim等人(2001),″Validation of an in vitro biofilmmodel of supragingival plaque″,J.Dent Res.第80卷第(1)期。
羟基磷灰石盘用人唾液预处理,各种革兰氏阳性和革兰氏阴性口腔生物(链球菌、链霉素放线菌、韦荣球菌&具核梭杆菌多形亚种&其它)的确定混合物的生物被膜和酵母菌(白念珠菌)允许在羟基磷灰石上生长。在4天的试验时间内,盘子浸入以下给定的物质(II)的适合配制剂中,总共几次,
十二烷基硫酸钠 | 1.00% |
乙醇 | 20.00% |
物质(II) | 0.5% |
PEG-40氢化蓖麻油 | 5.00% |
丙二醇 | 10.00% |
水 | 63.5% |
在结束后,采集生物被膜并测定活细胞的数目。
结果:
两个独立试验的结果如表3所示。和无活性物质的安慰剂制剂相比,烷氧基苯羧酸引起羟基磷灰石盘上生物被膜的细菌量显著地减少。
表3:
样品 | 2-十二烷氧基-苯甲酸(II)(漱口剂制剂) | 对照(安慰剂制剂) |
(均值)[CFU/盘]CFU=菌落形成单位 | 1.2×1051.7×105 | 5.1×1077.9×107 |
Claims (13)
2、根据权利要求1的用途,其中R1是取代或未取代的C8-C20烷基。
3、根据权利要求1和2的用途,其中式(I)化合物用于皮肤、口腔和其它粘膜,牙齿的表面,和毛发的抗菌处理、除臭和消毒。
4、根据权利要求1-3任一项所述的用途,其中式(I)化合物用于消毒和除臭。
5、根据权利要求1-4任一项所述的用途,其中式(I)化合物用于纺织纤维材料的处理。
6、根据权利要求1-5任一项所述的用途,其中式(I)化合物用于防腐。
7、根据权利要求1-6任一项所述的用途,其中式(I)化合物用于清洗或清洁制剂。
8、根据权利要求1-7任一项所述的用途,其中式(I)化合物用于给予塑料、纸、无纺布、木材、或皮革抗菌性或用于保存塑料、纸、无纺布、木材、或皮革。
9、根据权利要求1-8任一项所述的用途,其中式(I)化合物用于给予商业产品抗菌性或用于保存商业产品。
10、根据权利要求1-9任一项所述的用途,其中式(I)化合物在工业生产中用作灭菌剂。
11、一种个人护理制品,包括
a)基于制品总重量计的0.01-15%重量的权利要求1的式(I)化合物,和
b)化妆品可容许的辅助剂。
12、一种口腔组合物,包括
a)基于组合物总重量计的0.01-15%重量的权利要求1的式(I)化合物,和
b)口用可容许的辅助剂。
13、式(I)的化合物在防止微生物的生物被膜的积累和/或除去生物被膜和/或抑制或消灭形成生物被膜的微生物中的非治疗性用途。
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US (1) | US20070196407A1 (zh) |
EP (1) | EP1715832A1 (zh) |
JP (1) | JP2007526252A (zh) |
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WO (1) | WO2005079744A1 (zh) |
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EA202091213A1 (ru) | 2017-11-14 | 2020-08-13 | Юнилевер Н.В. | Пептиды для повышения содержания меланина в меланоцитах |
US11419803B2 (en) | 2017-12-06 | 2022-08-23 | Conopco, Inc. | Skin darkening composition |
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US4847088A (en) * | 1988-04-28 | 1989-07-11 | Dow Corning Corporation | Synergistic antimicrobial composition |
JPH1081607A (ja) * | 1996-09-06 | 1998-03-31 | Kamiyama:Kk | 抗菌剤 |
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