CN101374885A - 聚合物抗微生物剂 - Google Patents
聚合物抗微生物剂 Download PDFInfo
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- CN101374885A CN101374885A CNA2007800037150A CN200780003715A CN101374885A CN 101374885 A CN101374885 A CN 101374885A CN A2007800037150 A CNA2007800037150 A CN A2007800037150A CN 200780003715 A CN200780003715 A CN 200780003715A CN 101374885 A CN101374885 A CN 101374885A
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- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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Abstract
本发明提供通过取代乙烯亚胺聚合物主链中的氮原子而制备的聚合物抗微生物剂。认为该试剂具有低的人类毒性,同时可有效地对抗各种病原体,并且可用于涉及与人接触的应用例如化妆品、护发产品和织物,也可用于与人接触少得多的应用例如涂料。
Description
技术领域
本发明涉及衍生自聚乙烯亚胺(polyethylenimine)的聚合物抗微生物剂(polymeric anti-microbial agents)。所述聚合物抗微生物剂被认为对人类具有低毒性,同时能够有效对抗各种病原体,并且可用于涉及与人类接触的应用(例如化妆品、护发产品和织物)中,也可用于与人类接触少得多的应用(例如涂料)中。
背景技术
抗微生物化合物广泛用作多种产品和材料的一部分,并且得到了认可。抗菌皂、对植物进行抗真菌处理、局部医疗处置、防污涂层(anti-foulingcoatings)和消毒清洁剂仅仅是抗微生物材料的几种普通用途。
对抗微生物化合物的使用而言,明显困境是:这些化合物必须对活体有活性,但是对人类、动物或期望的植物是没有毒性的。本发明所披露的化合物能有效对抗各种有害微生物,并且预期比许多其它抗微生物化合物对人类的危害更小,这部分可归因于本发明化合物的聚合物性质。
美国专利6,090,772、5,955,408、6,071,866、6,358,906(在此引入它们的全部内容作为参考)和WO96/06152披露了包括三氯生作为抗细菌剂的组合物在个人应用中的用途。
美国专利5,635,462也披露了包括抗细菌剂的组合物,在此引入其全部内容,作为参考。
WO98/55096披露了抗微生物的擦拭物,其具有浸渍有包含活性抗微生物剂的抗细菌组合物的多孔片材。
美国专利6,861,397披露了个人护理和清洁组合物,其中包含抗细菌剂的局部活性化合物的沉积(deposition)得到了改善,在此引入其全部内容,作为参考。
美国专利6,872,241披露了对传染性空气传播的微生物具有保护能力的抗病原性空气过滤介质(anti-pathogenic air filtration media)和空气处理设备,在此引入其全部内容,作为参考。
美国专利3,116,969描述了具有氯化烷基芳基季铵盐防腐杀菌化合物(antiseptic compound)的过滤器,该化合物经由包括吸湿剂、增稠剂和成膜剂的粘性组合物而保持在过滤器纤维(filter fiber)上,在此引入其全部内容,作为参考。
从国际公开文本WO 00/64264的英文摘要可知,该国际公开文本披露了用于过滤器的杀菌有机聚合物材料,其由包括主链以及与主链连接的的聚合物侧基的聚合物基质制成,所述侧基包括衍生自N-烷基-N-乙烯基烷基酰胺和三碘离子(triiodide ion)的单元。
美国专利5,405,919披露了将生物活性的二醇二氮烯鎓NO-释放基团(biologically active diazeniumdiolate NO-releasing groups)与聚合物结合或偶联的方法,所述聚合物包括聚烯烃、聚乙烯亚胺、聚酯、聚醚、聚氨酯等,在此引入其全部内容,作为参考。
JP-09157113-A、JP 09012717-A和JP 07188698披露了使用烷基(C8~C30)、酰基和羟基烷基改性的聚乙烯亚胺作为抗微生物剂,在Zn盐、Cu盐和Ag盐的情况下,该抗微生物剂特别有效。
Klibanov,Biotechnol.Prog.2002,18,1082-1086;Biotech.and Bioengin.2003,83,168-172描述了有效作为抗微生物剂的N-烷基化的聚乙烯亚胺衍生物。
重要的是,抗微生物化合物(例如抗细菌组合物中存在的那些抗微生物化合物)能够迅速提供实质上和广谱性的微生物种群减少,而没有与毒性和皮肤刺激相关的问题。针对广谱的微生物进行抗细菌活性评价,包括革兰氏阳性和革兰氏阴性微生物。抗细菌组合物所提供的细菌种群的对数减少值(log reduction)或者减少百分比与抗细菌活性相关。对于具体的接触时间(通常为15秒~5分钟),对数减少值为3-5是最优选的,对数减少值为1-3是优选的,而对数减少值小于1是最低优选的。因此,高度优选的抗细菌组合物在短的接触时间内对广谱微生物显示出3-5的对数减少值。
对抗微生物溶液而言,现有技术采用鸡尾酒方法,该方法通过混合两种或多种抗微生物化合物提供了广谱的抗微生物活性。该方法常常与相容性问题相关,这是因为抗微生物化合物的物理性质和化学性质不同,例如,稳定性、溶解性和渗出率(leaching rate)不同。抗微生物聚合物的优点是,可通过将不同的官能团结合到相同的聚合物链上而实现广谱的抗微生物活性,而不会产生任何相容性问题。也可引入官能团来调整抗微生物聚合物的物理和化学性质,并因此改善它们在应用中的性能。我们的实验已经证明,通过进一步向聚合物链上引入官能团,能够显著增加抗微生物聚合物在水和/或二醇中的溶解性,而不会影响抗微生物的活性。
发明内容
本发明提供新的抗微生物聚乙烯亚胺化合物。这些聚合物和低聚物在与微生物接触时对微生物是高度活性的,并且在长时期里保持活性,这部分是由于它们的尺寸和聚合物性质导致的,它们的尺寸和聚合物性质使得它们更加不易于被无意间除去。所述化合物也被认为比其它化合物对人类接触时的危害更小,其它化合物更加容易吸收经过皮肤或者通过分散到环境中而变得生物可用(bio-available)。
本发明提供抗微生物的乙烯亚胺聚合物或共聚物,
其中所述聚合物或共聚物主链中10-100%的氮原子(在本申请中也称为N原子)被一个或多个取代基a-d取代:
a)C1-24烷基、C3-24烯基、C1-24烷基羰基或C3-24烯基羰基,所述基团是未被隔断的或被氧原子、硫原子、-SO-或-SO2-中的一个或多个隔断一次或多次,并且被一个或多个以下基团取代一次或多次:C3-6环烷基、-OR、-COOR、-COOM、-SO3M、-SO3H、膦酸基团(phosphonic acid)、卤素、-CONR’R、-NR’R、膦酸根(phosphonate salt)、铵根(ammonium salt)或式—L-Ar的基团,或基团-Si(G)3,其中G各自独立地为羟基、C1-4烷基或C1-4烷氧基,
条件是未被隔断的C1-24烷基不被以下基团取代:双胍、C3-6环烷基、-COOM、R是未取代的烷基的-COOR、R是H或未取代的烷基羰基的-OR或-CONR’R,除非所述C1-24烷基上也存在所述取代基中的至少一种另外的取代基;
b)下式的杂环:
或
其中Y和Y’独立地为N、C-R、C-OR或C-NRR’,D和D’独立地为R、-OR或-NRR’;
c)下式的基团:
其中m和n独立地为1、2、3、4、5或6;
或
d)-L-Poly,其中Poly是支化的或未支化的聚合物或低聚物,所述聚合物或低聚物选自聚醚、聚硅氧烷、苯乙烯聚合物或聚醇;
其中
R、R’和R”各自独立地为氢;
C1-24烷基、C3-24烯基、C3-6环烷基或C1-24烷基羰基,所述基团是未被隔断的或被氧原子、硫原子、羰基、-COO-、-CONH-、-NH-、-CON(C1-8烷基)-或-N(C1-8烷基)-中的一个或多个隔断一次或多次,所述未被隔断的或被隔断的烷基、烯基、环烷基或烷基羰基是未取代的或被一个或多个以下基团取代一次或多次:卤素、-OH、C7-12芳烷基、C2-12烷基羰基、C1-24烷氧基、C2-24烷基羧基、-COOM、-CONH2、-CON(H)(C1-8烷基)、-CON(C1-8烷基)2、-NH2,
-N(H)(C1-8烷基)、-N(C1-8烷基)2、-SO3M、苯基、被一个或多个C1-8烷基取代一次或多次的苯基、萘基、被一个或多个C1-8烷基取代一次或多次的萘基、嘌呤、吡啶、嘧啶、三嗪或咪唑,所述嘌呤、吡啶、嘧啶、三嗪或咪唑是未取代的或被一个或多个C1-12烷基取代,其中所述嘌呤、吡啶、嘧啶、三嗪或咪唑是中性的或离子带电的、脒、胍、铵根、膦酸基团、膦酸根或基团其中Q或Q’各自独立地为氢、C1-12烷基、苯基或苄基;
或者
当R和R’与氮原子连接时,R和R’与它们所连接的氮原子一起形成5-、6-或7-元环,所述环是未被隔断的或被-O-、-NH-或-N(C1-12烷基)-隔断;
L是直接键、C1-12亚烷基,所述C1-12亚烷基是未被隔断的或被一个或多个氧原子隔断,并且所述C1-12亚烷基是未取代的或被一个或多个以下基团取代一次或多次:-OH、C1-8烷基、C1-24烷氧基、C2-24烷基羧基、-NH2、-N(H)(C1-8烷基)、-N(C1-8烷基)2或铵根:
Ar是C6-10芳族基团或饱和的或不饱和的C1-9杂环,所述芳族基团或杂环是未取代的或被一个或多个以下基团取代一次或多次:卤素、-OH、C1-24烷氧基、C2-24烷基羧基、-COOQ”、-CONH2、-CON(H)(C1-8烷基)、-CON(C1-8烷基)2、-NH2、-N(H)(C1-8烷基)、-N(C1-8烷基)2、-SO3M、SO3H、铵根、膦酸基团、膦酸根,未取代的或被一个或多个卤素取代一次或多次的C1-24烷基、未取代的或被一个或多个C1-8烷基取代一次或多次的苯基、萘基、嘌呤、吡啶、嘧啶、三嗪或咪唑,所述嘌呤、吡啶、嘧啶、三嗪或咪唑是未取代的或被一个或多个C1-12烷基取代,其中所述嘌呤、吡啶、嘧啶、三嗪或咪唑是中性的或离子带电的;
其中Q”是氢、金属阳离子、二醇醚(glycol ether)、聚硅氧烷、苯基或苄基;或被卤素、羟基、C1-24烷氧基或C1-12烷基中的一个或多个取代一次或多次的苯基或苄基,
M是金属阳离子或铵阳离子,
并且当所述乙烯亚胺聚合物的N原子被四取代时,它是具有相应抗衡阴离子的阳离子。
例如,本发明提供如上所述的抗微生物的乙烯亚胺聚合物或共聚物,其中至少部分的所述取代基是C1-24烷基、C3-24烯基、C1-24烷基羰基或C3-24烯基羰基,所述基团是未被隔断的或被氧原子、硫原子、-SO-或-SO2-中的一个或多个隔断一次或多次,和被一个或多个以下基团取代一次或多次:-OR、-COOR、-COOM、-NR’R、-SO3M、-SO3H、卤素、-NR’R、铵根或式—L-Ar或的基团,
条件是未被隔断的C1-24烷基不被以下基团取代:双胍、-COOM、R是未取代的烷基的-COOR,或R是H或未取代的烷基羰基的-OR,除非所述C1-24烷基上也存在所述取代基中的至少另一种基团;
例如,一种抗微生物的乙烯亚胺聚合物或共聚物,其中至少部分的所述取代基是C1-24烷基或C1-24烷基羰基,所述C1-24烷基或C1-24烷基羰基被一个或多个以下基团取代:卤素、铵根、-L-Ar、或其中R是-L-Ar或的-OR;
例如一种抗微生物的乙烯亚胺聚合物或共聚物,其中至少部分的所述取代基是被卤素或铵根中的一个或多个取代一次或多次的C1-24烷基,被卤素或铵根中的一个或多个取代一次或多次的C1-24烷基羰基,或者至少部分的所述取代基是苄基、苯甲酰基;或被卤素、羟基、C1-12烷基、C1-12烷氧基或C1-12烷基羧基中的一个或多个取代一次或多次的苄基或苯甲酰基;
例如一种抗微生物的乙烯亚胺聚合物或共聚物,其中至少部分的所述取代基是被选自铵根、苯氧基、苄氧基、取代的苯氧基、取代的苄氧基、苄基、取代的苄基、和中的至少一个基团取代的C1-24烷基或C1-24烷基羰基,其中n是1~12的数;
例如,抗微生物的乙烯亚胺聚合物或共聚物主链中10-100%的N原子至少部分是取代的,且被一个或多个C1-24烷基取代,所述C1-24烷基烷基被至少一个基团OR取代和被卤素、NR’R、SO3M、SO3H、铵根或式 Ar、或的基团中的至少一种取代;
例如,本发明提供抗微生物的乙烯亚胺聚合物或共聚物,其中抗微生物的乙烯亚胺聚合物或共聚物主链中10-100%的N原子至少部分是取代的,所述取代基选自:
C2-24烷基,C2-24烷基羰基,C3-24烯基,和C3-24烯基羰基,所述基团被氧原子、硫原子、-SO-或-SO2-中的一个或多个隔断一次或多次,是未取代的或被以下基团中的一个或多个取代的一次或多次:卤素、-OR、-COOR、-COOM、-CONR’R、-NR’R、-SO3M、-SO3H、膦酸基团、膦酸根、铵根或式或-L-Ar的基团;
例如,本发明提供抗微生物的乙烯亚胺聚合物或共聚物,其中聚合物或共聚物主链中10-100%的氮原子至少部分是取代的,且被下式中的一个或多个取代,
或
其中Y和Y’独立地为N、C-R、C-OR或C-NRR’和
D和D’独立地为R、OR或NRR’;
例如,抗微生物的乙烯亚胺聚合物或共聚物,其中至少部分的所述取代基是
D和D’独立地为R、OR或NRR’,其中R和R’独立地为氢,铵根,C1-24烷基,C1-24烷酰基,所述C1-24烷基,C1-24烷酰基是未取代的或被卤素、羟基或铵根中的一个或多个取代一次或多次;或者R和R’独立地为-L-Ar、或
其中L是直接键或C1-12亚烷基,和
Ar是苯基和被一个或多个以下基团取代一次或多次的苯基:卤素、-OH、C1-24烷氧基、C2-24烷基羧基、-COOH、-COOM、-CONH2、-CON(H)(C1-12烷基)、-CON(C1-12烷基)2、-NH2、-N(H)(C1-12烷基)、-N(C1-12烷基)2、铵根、C1-12烷基或烷基,所述C1-12烷基或烷基被一个或多个卤素取代一次或多次。
例如,抗微生物的乙烯亚胺聚合物或共聚物主链中10-100%的氮原子至少部分是取代的,且被以下基团取代:
基团-L-Poly,其中Poly是选自聚醚和聚硅氧烷的聚合物或低聚物;
饱和的或不饱和的C1-9杂环是至少3个原子的单环或多环,所述杂环含有1-9个碳原子且也可是离子带电的。
例如,饱和的或不饱和的C1-9杂环是含有1、2或3个氮原子的5、6或7元环,其可与另一碳环或杂环稠合;
例如,饱和的或不饱和的C1-9杂环是含有1、2或3个氮原子的5、6或7元环,其可与苯环稠合;
例如,饱和的或不饱和的C1-9杂环是嘌呤、咪唑、吡啶、嘧啶(pyramidine)或三唑环;
其中所述杂环可如上所述被取代,并且该杂环也可以是离子带电的。
烷基是具有指定数目的碳原子的直链或支链,例如为甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十六烷基、正十八烷基或二十二烷基等。
烯基是含有一个或多个碳碳双键且具有指定数目的碳原子的直链或支链,例如为正丙烯基、正丁烯基、仲丁烯基、正己烯基、正辛烯基、正己二烯、正辛二烯、2-乙基己烯基、正壬烯基、正癸烯基、正十一碳烯基、正十二碳烯基、正十三碳烯基、正十四碳烯基、正十六碳烯基、正十八碳烯基、正十八碳二烯基、正十四碳二烯基、正十六碳二烯基、正十六碳三烯基、正十八碳二烯基、正十八碳三烯基。
烷酰基在连接点具有羰基的具有指定数目的碳原子的直链或支链。
铵盐为例如未取代的铵,被一种或多种选自以下的基团取代1、2或3次的铵:
C6-10芳基、C1-24烷基、C1-24支化烷基、被一个或多个氧原子、羰基、羧基或C6-10亚芳基隔断的C1-24烷基和被一个或多个氧原子、羰基、羧基或C6-10亚芳基隔断的C1-24支化烷基,
和被烷基、芳基、OH、烷氧基(OAlkyl)、酰氧基(OAcyl)取代的所述芳基、烷基、支化烷基、隔断的烷基和隔断的支化烷基;加上相应的抗衡阴离子。
铵盐也可包括环或多环,该环或多环可被取代。
例如,铵盐是三苄基铵、单-C1-24烷基铵、二-C1-24烷基铵、三-C1-24烷基铵,其中每个烷基可相同或不同;单-苄基铵、二-苄基铵、三-苄基铵、单-C1-24羟基烷基铵、二-C1-24羟基烷基铵或三-C1-24羟基烷基铵,其中每个烷基可为相同或不同。
例如,铵盐为二-或三-取代的铵,其中每个取代基独立地选自C1-24烷基、苄基和C1-24羟基烷基。
所述取代的铵盐的C1-24烷基、苄基和C1-24羟基烷基也可被C1-8烷基或支化烷基、羟基、C1-24羧酸酯基、C1-24烷氧基、C1-24酰氧基或卤素取代。
当M是铵阳离子时,它为例如未取代的铵,
被一种或多种选自以下的基团取代1、2、3或4次的铵:
C1-24烷基、C1-24支化烷基、被氧原子、C6-10芳基、C7-9芳烷基中的一个或多个隔断的所述烷基和支化烷基,和被烷基、OH、OC1-24烷基、OC1-24酰基取代的所述烷基、支化烷基、隔断的烷基、隔断的支化烷基和芳基。
乙烯亚胺聚合物或共聚物的N原子可被许多种不同的上述取代基、几种上述取代基或一种上述取代基取代。单个取代基不需要取代乙烯亚胺聚合物或共聚物主链中10%或以上的N原子,只要上述其它取代基(在下文中也称为本发明的取代基)也存在并使得至少10%的N原子被一种或多种本发明的取代基取代即可。
本发明的取代基的实例包括:
苄基、苯甲酰基、
被卤素、C1-8烷基、铵根、羟基、酰氧基、羧酸、酸式盐(acid salt)和/或酯基中的一个或多个取代的苄基或苯甲酰基;
铵根、苯基、萘基、取代的或未取代的杂环例如嘌呤、吡啶、嘧啶、嘧啶或三嗪中的一个或多个取代的C1-24烷基或烷基羰基;
C1-24烷基或烷基羰基,所述C1-24烷基或烷基羰基被铵根、卤素、基团OR、苯基、萘基、取代的或未取代的杂环中的一个或多个取代,也带有至少一种其它不同的取代基,所述取代基选自卤素、羟基、酰氧基、羧酸、酸式盐和/或酯基,例如被羟基和卤素取代的烷基,或酰基和取代的嘌呤;
被氧隔断和被以下基团取代的C1-24烷基:苄基、苯甲酰基、取代的苄基、取代的苯甲酰基、取代的或未取代的杂环例如嘌呤、吡啶、嘧啶、嘧啶、三嗪、进一步被所述杂环或一个或多个卤素取代的酰基。
未取代的或被C1-8烷基、烷基胺、芳基胺、苯基、苄基、取代的苯基或苄基、酰氧基、羧酸、酸式盐和/或酯基中的一个或多个取代的杂环例如嘌呤、嘧啶或三嗪杂环。
例如本发明的取代基选自:
被F、Cl、Br或I,或F、Cl、Br或I的任何组合取代1-5次的苄基;
下式的嘧啶或三嗪:
其中Y是CR或N;
被一个或多个以下基团取代的C1-24烷基或烷基羰基:
被一个或多个以下基团取代的C1-24烷基或烷基羰基:
其中Y是C或N。
例如,本发明的取代基包括以下结构式,以下结构式的异构体和所述结构式的类似物以及所述异构体的类似物:
其中Y、Y’和Y”是C或N,R如以上所定义。
在本发明的一种实施方式中,抗微生物的乙烯亚胺聚合物或共聚物主链中10-100%的N原子至少部分被烷基取代,所述烷基被选自下式中的至少两种不同的基团取代:OR、COOM、卤素、CONR’R、NR’R、SO3M、SO3H、膦酸基团、膦酸根、铵根或下式的基团,
乙烯亚胺聚合物或共聚物可被提供不同活性的基团取代。例如,该聚合物可带有使聚合物抗细菌的取代基和使聚合物抗真菌的其它取代基。
在本发明的一种实施方式中,单个乙烯亚胺聚合物、共聚物或低聚物包括至少两种不同的取代基,其中取代基各自提供不同的抗微生物活性,例如,聚合物的N原子带有两种不同的取代基,每种取代基提供不同的活性。
在另一实施方式中,单个N原子取代基带有提供不同活性的至少两种不同的取代基,例如,N原子被烷基取代,所述烷基被两个基团取代,一个基团提供抗细菌活性,另一个基团提供抗真菌活性。
在另一实施方式中,将至少两种不同的本发明的乙烯亚胺聚合物,共聚物或低聚物共混。
在另一实施方式中,将本发明的乙烯亚胺聚合物、共聚物或低聚物与另一种抗微生物化合物共混。
除了上述的本发明的取代基之外,以上未提及的取代基,例如,简单的烷基取代基如C1-24烷基或被羟基、羧基或羧酸酯基取代的C1-24烷基也可作为另外的取代基存在于乙烯亚胺聚合物或共聚物的N原子上。
剩余的氮原子可以是未取代的或被C1-24烷基或被-OR、COOR、COOM取代的所述烷基取代,其中R和M如上所述。因此本发明包括乙烯亚胺聚合物和共聚物,其中10-100%,尤其是10-99%的氮原子带有本发明的取代基,而剩余的氮原子(例如1-90%)是未取代的,或被C1-24烷基或被-OR、COOR、COOM取代的所述烷基取代,其中R和M如上所述,或者一部分是未取代的,而剩余的被C1-24烷基或被-OR、COOR、COOM取代的所述烷基取代,其中R和M如上所述。
例如,本发明也涉及如权利要求1的抗微生物的乙烯亚胺聚合物或共聚物,其中乙烯亚胺聚合物或共聚物主链的N原子的10-99%如上所述被取代,和乙烯亚胺聚合物或共聚物主链中至少1%的N原子被C1-24烷基或被-OR、COOR、COOM取代的所述烷基取代,其中R和M如上所述。
乙烯亚胺聚合物或共聚物主链的任何氮原子也都可被相同的取代基取代不止1次,或者被不止1种取代基取代。
例如,聚合物或共聚物主链中部分N原子可被苄基取代,一部分被氯苄基取代,一部分被苄基和氯苄基取代。例如,聚合物或共聚物主链中10%或更多的N原子可被羟基和铵阳离子取代的烷基链取代,剩余的主链N原子的一部分被简单的烷基取代。
可通过已知的下述反应对预先存在的聚合物的N原子进行取代,或者通过对乙烯亚胺单体或低聚物的N原子进行取代,然后进行接下来的聚合反应,而容易地制备本发明的取代的乙烯亚胺聚合物或共聚物。这种预先存在的聚合物是可以以“预聚物”商购的,它是可聚合的乙烯亚胺单体或低聚物。
取代之前,聚合物或共聚物的分子量为300~50000,通常为400~50,000,例如400~5,000,并且可为支化的或未支化的。该聚合物也可以是固有交联的,即,通过基于乙烯亚胺物质的反应而交联,或通过试剂例如表氯醇、二环氧化物、环氧树脂或酐交联。
本发明将要被取代的所存在的乙烯亚胺聚合物、共聚物或低聚物的N原子可为单-,二-,或三-取代的胺,这取决于支化和交联的量。因此每个N原子具有一个或多个本发明的或非本发明的取代基,并且该聚合物或共聚物可为阳离子。
通过任何已知的胺取代反应使乙烯亚胺聚合物、共聚物或低聚物的N原子被取代。例如,可在合适的条件下通常是在碱存在下,通过与烷基、芳基或杂环的卤化物、磺酸酯、环氧化物等的反应而使胺被烷基化、芳基化或被杂环取代。胺的烷基化反应也在与乙烯基酯、酰胺、腈、砜等的反应中通过双键的加成而发生。胺可通过与酰基卤、酯、酐、羧酸等的反应而被酰基化。也已知各种金属催化的反应,例如Heck and Suzuki反应,对胺进行衍生化。
反应条件将决定聚合物或共聚物主链的N原子的取代量。例如,当用烷基卤化物对N原子进行烷基化时,在该反应中所用的烷基卤化物的量代表可结合的烷基化试剂的量的上限。如上所述,在该反应条件下,聚合物或共聚物主链的N原子可被取代不止1次。因此,通常选择在该反应中所用的取代试剂的量,使其提供的取代比例为0.2~2摩尔当量取代基/摩尔聚合物所含的N原子。所述烷基卤化物是商业产品或容易通过已知方法制备。
例如,取决于条件,聚乙烯亚胺与苄基臭的反应将产生含有以下基团的取代的聚合物,
和其它苄基氨基(benzyl amino)基团,包括苄基仲氨基和苄基伯氨基。
本发明的抗微生物的乙烯亚胺聚合物或共聚物显示出延长的抗微生物的作用,例若,抗致病性革兰氏阳性和革兰氏阴性细菌和抗皮肤菌从(skinflora)的细菌,以及抗酵母和霉菌。因此它们适合用于灭菌、除臭、和皮肤和粘膜以及外皮附器(毛发)的一般处理和抗微生物处理,例如,用于手和伤口的灭菌。
因此它们适合在个人护理制剂中作为抗微生物活性物质和防腐剂,所述在个人护理制剂例如香波、沐浴添加剂、护发制剂、液体和固体皂(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)、露和霜、除臭剂、其它含水或醇的溶液如皮肤清洁溶液、湿的除尘器用布(moist cleaningcloth)、油或粉。
因此本发明也涉及包括至少一种本发明的抗微生物的乙烯亚胺聚合物或共聚物和化妆品容许的载体或助剂的个人护理制剂。
本发明的个人护理制剂含有本发明组合物总重量的0.01~15wt%,例如0.1~10wt%本发明的抗微生物的乙烯亚胺聚合物或共聚物,和化妆品容许的助剂。
取决于个人护理制剂的形式,它除了包括抗微生物的乙烯亚胺聚合物或共聚物之外,还包括组分例如掩蔽剂、色料、芳香油、增稠剂或固化剂(稠度调节剂)、柔润剂、UV-吸收剂、皮肤保护剂、抗氧化剂、改善机械性能的添加剂,例如二羧酸和/或C14-C22脂肪酸的铝盐、锌盐、钙盐或镁盐,以及任选的防腐剂。
根据本发明的个人护理制剂可为油包水或水包油乳液、醇或含醇制剂、离子或非离子两亲脂质的囊状分散体、凝胶、固体棒或气溶胶制剂的形式。
作为油包水或水包油乳液,化妆品容许的助剂含有优选5~50%的油相,5~20%的乳化剂和30~90%的水。油相可包括任何施用于化妆品制剂的油,例如一种或多种烃油、蜡、天然油、硅油、脂肪酸酯或脂肪醇。优选的一元醇或多元醇是乙醇、异丙醇、丙二醇、己二醇、甘油和山梨醇。
根据本发明的化妆品制剂可用于各种领域。可考虑例如例如以下制剂:
-护肤剂,如片剂形式或液体皂、合成洗涤剂或洗涤糊剂形式(washingpaste)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);
-个人护理制剂,如以日霜或粉霜(powder cream)、扑面粉(散粉或粉饼)、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、亮唇膏(lip gloss)、唇线笔(lip contour pencil);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;
-私人卫生制剂,例如私人洗液或私人喷雾;
-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、防晒露、防晒霜、防晒油、防晒剂(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;
-去色素制剂(depigmenting preparation),如漂白皮肤用的制剂或皮肤光亮制剂(skin-lightening preparation);
-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,如合成洗涤剂(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),如脱毛粉,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形式的脱毛剂;
-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),芳香油或香料霜(perfume creams);
-牙科护理,假牙护理和口腔护理制剂,例如牙膏,凝胶型牙膏(geltoothpaste),牙粉,嗽口剂浓缩液,抗牙菌斑漱口剂,假牙清洁剂或假牙固定剂;
-化妆品毛发处理制剂,如香波和毛发调理剂形式的毛发洗涤制剂,护发制剂,如预处理制剂、生发油(hair tonics)、造型乳膏(styling cream)、造型凝胶(styling gels)、润发脂(pomade)、发用漂洗剂、处理包、深入的毛发处理剂,毛发结构化制剂,如用于烫发(热烫、温烫、冷烫)的烫发制剂,毛发拉直制剂,液体毛发定型制剂,毛发泡沫(hairfoam),毛发喷雾,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,暂时性、半长效或长效毛发着色剂,包含自氧化染料、或天然毛发着色剂如指甲花染料或甘菊的制剂的制剂。
抗微生物肥皂具有例如以下组成:
0.01~5wt%速溶的(instant)抗微生物聚合物,
0.3~1wt%二氧化钛,
1~10wt%硬脂酸,
余量的皂基,例如牛油脂肪酸或椰油脂肪酸的钠盐,或甘油的钠盐。
香波具有例如以下组成:
0.01~5wt%速溶的抗微生物聚合物,
12.0wt%月桂基聚氧乙烯(2)醚硫酸钠,
4.0wt%椰油酰氨基丙基甜菜碱,
3.0wt%NaCl和
余量的水。
除臭剂具有例如以下组成:
0.01~5wt%速溶的抗微生物聚合物,
60wt%乙醇,
0.3wt%芳香油,和
余量的水。
本发明也涉及口腔组合物,其含有组合物总重量的0.01~15wt%速溶的抗微生物聚合物,和口腔容许的助剂。
口腔组合物的实例:
10wt%山梨醇,
10wt%甘油,
15wt%乙醇,
15wt%丙二醇,
0.5wt%月桂基硫酸钠,
0.25wt%甲基椰油酰基牛磺酸钠,
0.25wt%聚氧丙烯/聚氧乙烯嵌段共聚物,
0.10wt%薄荷调味剂(peppermint flavouring),
0.1~0.5wt%式(1)的化合物,和
48.6wt%水。
本发明的口腔组合物可为例如凝胶、糊剂、霜或含水制剂(漱口剂)的形式。
本发明的口腔组合物也可包括释放氟离子的化合物,其能够有效地对抗龋齿的形成,例如无机氟化物盐,例如氟化钠、氟化钾、氟化铵或氟化钙,或有机氟化物盐,例如胺氟化物,其以商品名Olafluor得知。
本发明抗微生物的乙烯亚胺聚合物或共聚物也适合用于处理,尤其是保护织物纤维材料。这种材料是未染色的和染色的或印刷的纤维材料,例如由丝、羊毛、聚酰胺或聚氨酯,和尤其是各种类型的纤维素纤维材料制成的材料。这种纤维材料是例如天然纤维素纤维,例如棉花,亚麻制品,黄麻和大麻(hemp),以及纤维素和再生纤维素。
本发明的抗微生物的乙烯亚胺聚合物或共聚物适合用于处理,尤其是赋予塑料抗微生物性质或使塑料防腐,所述塑料例如聚乙烯、聚丙烯、聚氨酯、聚酯、聚酰胺、聚碳酸酯、胶乳等。因此应用领域是例如,地板覆盖物(floor covering)、塑料涂层、塑料容器和包装材料;厨房和浴室用具(例如刷子、淋浴帘、海绵(sponge)、浴室防滑垫(bathmats))、胶乳、过滤材料(空气和水的过滤器);医学领域使用的塑料制品,例如绷扎材料(dressingmaterial),注射器,导管(catheter)等,所谓的"医疗器械",手套和床垫。
本发明的抗微生物的乙烯亚胺聚合物或共聚物也适合用于处理,尤其是赋予工业制剂抗微生物性质或使工业制剂防腐,所述工业制剂例如涂料,润滑剂等。
也可使用本发明的抗微生物的乙烯亚胺聚合物或共聚物给纸例如用于卫生目的的纸提供抗微生物性质。
也可将其用于需要根据本发明赋予抗微生物性质的非纺织制品,例如尿布(nappy)/尿布(diaper)、卫生巾(sanitary towel)、女裤护垫(panty liner)和用于卫生和家用用途的衣服。
本发明的抗微生物的乙烯亚胺聚合物或共聚物也用于洗涤和清洁制剂,例如用于液体或粉末形式的洗涤剂或柔软剂。
尤其是,也可将本发明的抗微生物的乙烯亚胺聚合物或共聚物用于对硬表面进行清洁和灭菌的家用和多用途的清洁剂中。
清洁制剂具有例如以下组成:
0.01~5wt%式(1)的化合物
3.0wt%辛醇氧乙烯(4)醚(octyl alcohol 4EO)
1.3wt%脂肪醇C8-C10多聚葡糖苷
3.0wt%异丙醇
余量的水。
除了对化妆品用和家用产品进行防腐之外,也可用于对工业产品进行防腐,提供具有抗微生物性质的工业产品和在工艺流程(technical process)中用作生物杀灭剂,例如在纸处理尤其是在纸处理液(treatment liquor)、淀粉或纤维素衍生物的印刷增稠剂、表面涂料和油漆中使用。
本发明的抗微生物的乙烯亚胺聚合物或共聚物也适合用于木材的抗微生物处理和皮革的抗微生物处理,皮革的防腐和提供具有抗微生物性质的皮革。
本发明的化合物也适合用于保护化妆品产品和家用产品不受微生物损害。
共同未决申请60/720,662披露了可在涂料或膜中用于保护表面不产生生物淤积的化合物,将该申请的全部内容引入本申请,作为参考。这种表面包括与海洋环境(包括淡水环境、微咸水环境和盐水环境)接触的表面,例如船体、船坞表面或水循环或流通系统中的管内侧。其它表面也易于产生类似的生物淤积,例如暴露于雨水的墙壁、淋浴的墙壁(walls of shower)、屋顶、排水沟、池塘区域、桑拿室、暴露于潮湿环境的地板和墙壁例如地下室或车库,甚至是工具和户外设备的外壳。
本发明的抗微生物的乙烯亚胺聚合物或共聚物也可用于:通过将抗微生物的乙烯亚胺聚合物或共聚物加入到所关心的制品或制品的表面中,或者通过将抗微生物的乙烯亚胺聚合物或共聚物直接地或作为涂料或膜的一部分施用到这些表面上,而防止在共同未决申请60/720,662中披露的表面上生物淤积,或者消除或控制在共同未决申请60/720,662中披露的微生物表面上的积聚,如共同未决申请60/720,662中所述。
当作为膜或涂料的一部分施用时,本发明的抗微生物的乙烯亚胺聚合物或共聚物是组合物的一部分,所述组合物也包括粘合剂。
粘合剂可为与本发明的抗微生物剂相容的任何聚合物或低聚物。所述粘合剂可以在制备防污组合物之前是聚合物或低聚物的形式,或者可以在制备的过程中或在制备之后(包括在施用至基材之后)通过聚合反应形成。在某些应用例如某些涂料应用中,会期望在施用之后使防污组合物的低聚物或聚合物交联。
在本发明中所用的术语粘合剂也包括材料例如在木材、塑料、玻璃和其它表面的护理中商业用的二醇类、油、蜡和表面活性剂。实例包括木材的防水材料、乙烯基防护剂、防护蜡等。
该组合物可为涂料或膜。当该组合物是通过使用粘着剂或熔融施涂方法施用到表面上的热塑性膜时,粘合剂是用于制备该膜的热塑性聚合物基质,所述熔融施涂方法包括压延和共挤出。
当组合物是涂料时,可将其作为液体溶液或悬浮液、糊剂、凝胶、油而施用(或者所述涂覆组合物可为固体,则通过例如粉末涂布而施用),接着通过加热、紫外光或其它方法使其固化。
由于本发明的组合物可为涂料或膜,所以该粘合剂可由涂料制剂或膜制品(film preparation)中所用的任何聚合物组成。例如,该粘合剂是热固性、热塑性、弹性、内在交联的或交联的聚合物。
热固性、热塑性、弹性、内在交联的或交联的聚合物包括聚烯烃、聚酰胺、聚氨酯、聚丙烯酸酯、聚丙烯酰胺、聚碳酸酯、聚苯乙烯、聚乙酸乙烯酯、聚乙烯醇、聚酯、卤化的乙烯基聚合物例如PVC、天然和合成橡胶、醇酸树脂、环氧树脂、不饱和的聚酯、不饱和的聚酰胺、聚酰亚胺、含硅的氨基甲酸酯(或盐)聚合物(silicon containing and carbamate polymer)、氟化的聚合物、衍生自取代的丙烯酸酯的可交联的丙烯酸类树脂,所述取代的丙烯酸酯例如衍生自环氧丙烯酸酯、聚氨酯丙烯酸酯或聚酯丙烯酸酯。所述聚合物也可为前述化合物的共混物和共聚物。
可生物相容的涂料聚合物如聚[-烷氧基链烷酸酯-共聚-3-羟基链烯酸酯](PHAE)聚酯(Geiger et.al.Polymer Bulletin 52,65-70(2004))也可用作本发明的粘合剂。
醇酸树脂、聚酯、聚氨酯、环氧树脂、含硅聚合物、氟化聚合物和乙酸乙烯酯的聚合物、乙烯醇和乙烯基胺是在本发明中有用的普通涂层粘合剂(coating binder)的非限制性实例。当然其它涂层粘合剂也是本发明的一部分。
常常使用例如三聚氰胺树脂、脲醛树脂、异氰酸酯、异氰脲酸酯、聚异氰酸酯、环氧树脂、酐、多元酸和胺,在存在或不存在促进剂的情况下使涂层交联。
本发明的组合物是例如施用到暴露于容易产生生物淤积的表面的涂料。在所述涂料中存在本发明的抗微生物的乙烯亚胺聚合物或共聚物将防止有机体粘附到该表面上。
本发明的抗微生物化合物可为完整的涂料或油漆制剂例如海用凝胶涂层(marine gel-coat)、虫胶、清漆、真漆(lacquer)或油漆的一部分,或者所述防污组合物可仅包括本发明的聚合物和粘合剂,或者本发明的聚合物、粘合剂和载体物质。可以预期,也可将在这种涂料制剂或应用中使用的其它添加剂任选地用于本发明的应用。
所述涂料可以是含有溶剂的或者是水性的。通常认为水性的是更加环境友好的。
所述涂料是例如本发明的聚合物和基于粘合剂或水的涂料或油漆的水分散体。例如,所述涂料包括本发明的聚合物和丙烯酸类、甲基丙烯酸类或丙烯酰胺类聚合物或共聚物或聚[-烷氧基链烷酸酯-共聚-3-羟基链烯酸酯]聚酯的水分散体。
所述涂料是例如在海上应用中使用的涂料或清漆。
可将该涂料施用至已经涂覆了的表面上,例如保护性涂层、透明涂层或已经施用于前面涂覆的制品的外层的保护性蜡上。
涂料系统(Coating system)包括海用涂料,木材涂料(wood coating),用于金属的其它涂料和塑料和陶瓷上的涂料。海用涂料的示例是包括不饱和聚酯、苯乙烯和催化剂的凝胶涂料。
所述涂料是例如建筑用漆(house paint),或其它装饰涂料(decorativepaint)或防护漆(protective paint)。它可为施用至水泥、混凝土或其它石工制品上的油漆或其它涂料。对于地下室或地基,所述涂料可为防水材料(waterproofer)。
由于意图将防污组合物用于海事应用中以及池塘附近的区域等,所以该组合物可为防滑涂料的一部分,所述防滑涂料包括用于阶梯、道路和扶手的涂料。
通过任何常规的方法将该涂覆组合物施用至表面,所述方法包括旋涂、浸涂、喷涂、刮涂(draw down),或者通过刷子、辊子或其它涂抹器涂覆。通常会需要干燥期(drying period)或养护期。
涂料厚度或膜厚度将根据应用而变化,它将在有限的试验之后对本领域技术人员来说变得显而易见。
组合物可为保护性层压膜的形式。
这种膜通常包括热固性、热塑性、弹性或交联的聚合物。这种聚合物的实例包括但不限于聚烯烃、聚酰胺、聚氨酯、聚丙烯酸酯、聚丙烯酰胺、聚碳酸酯、聚苯乙烯、聚乙酸乙烯酯、聚乙烯醇、聚酯、卤化的乙烯基聚合物例如PVC、天然和合成橡胶、醇酸树脂、环氧树脂、不饱和的聚酯、不饱和的聚酰胺、聚酰亚胺、氟化的聚合物、含硅的聚合和氨基甲酸酯聚合物。所述聚合物也可为前述化合物的共混物和共聚物。
当所述防污组合物是预成型的膜时,就通过例如使用粘合剂将它施用到表面上,或者将它共挤出到表面上。也可通过紧固件将它机械固定,这可能需要使用密封剂或嵌缝胶(caulk),在所述密封剂或嵌缝胶中也可有利地使用本发明的酯。
也可借助于热方法来施涂塑料膜,所述热方法包括压延、熔融施涂(meltapplication)和收缩包装。
该组合物可为以下制剂的一部分:上光剂,如家具擦光漆(furniturepolish),或分散剂或表面活性剂制剂例如二醇或矿物油分散体,或用于例如木材保护的其它制剂。
有用的表面活性剂的实例包括但不限于基于聚氧乙烯的表面活性物质,其包括聚氧乙烯失水山梨醇醚四油酸酯(PST)、聚氧乙烯山梨醇六油酸酯(PSH)、聚氧乙烯(6)十三烷基醚、聚氧乙烯(12)十三烷基醚、聚氧乙烯(18)十三烷基醚、TWEEN RTM表面活性剂、TRITON RTM表面活性剂,以及聚氧乙烯-聚氧丙烯共聚物例如PLURONIC RTM和POLOXAMER RTM产品系列(得自BASF)。其它形成基质的组分包括葡聚糖、直链PEG分子(MW500~5,000,000)、星形PEG分子、梳形和树枝状、超支化的(hyperbrached)PEG分子,以及类似的直链、星形和树枝状聚胺聚合物(polyamine polymer),和各种碳酸酯化的表面活性剂、全氟化的表面活性剂(例如,DUPONT ZONYLRTM含氟表面活性剂)和硅化的表面活性剂(例如,二甲基硅氧烷-氧化乙烯嵌段共聚物)。
对于本发明的抗微生物组合物的广泛应用,该组合物可含有其它添加剂例如抗氧化剂、UV吸收剂、受阻胺、磷酸式盐(或酯)或膦酸式盐(或酯)、苯并呋喃-2-酮、含硫增效剂(thiosynergist)、聚酰胺稳定剂、金属硬脂酸式盐、成核剂、填料、增强剂、润滑剂、乳化剂、染料、颜料、分散剂、其它光学增亮剂、阻燃剂、防静电剂、发泡剂等,例如以下所列的材料,或其混合物。
基材可为无机基材或有机基材例如金属或金属合金;如上所述的热塑性、弹性、内在交联的或交联的聚合物;天然聚合物例如木材或橡胶;陶瓷材料;玻璃;皮革或其它织物。
基材可为例如非金属无机表面例如硅石(silica)、二氧化硅、氧化钛、氧化铝、氧化铁、碳、硅、各种硅酸式盐和溶胶凝胶、砌石(masonry)和复合材料例如玻璃纤维和塑料木材(plastic lumber)(聚合物与木材刨花、木粉或其它木材颗粒的共混物)。
无机或有机基材是例如金属或金属合金,热塑性、弹性、内在交联的或交联的聚合物,陶瓷材料或玻璃。
基材可为每层中由相同或不同的组分组成的多层制品。涂覆的或层压的表面可以是已经施涂的涂层或层压物的暴露表面。
要涂覆或层压的无机或有机基材可为任何固体形式。
例如,聚合物基材可为膜、注塑制品、挤出的工件、纤维、毡或纺织品形式的塑料。
例如用于构建和制造耐久品(如壁板、绷带(fascia)和邮箱)的模塑的或挤出的聚合物制品都可由于得益于本发明的方法而增加了稳定性。
可得益于本发明的方法的塑料包括但不限于用于构建或制造耐久品或机器零件的塑料,所述耐久品或机器零件包括户外设备、船、壁板、屋顶、釉(glazing)、保护膜、贴花膜(decal)、密封剂、复合物如塑料木材和纤维增强的复合物、功能膜(functional film),其包括用于显示器中的膜、以及由合成纤维构造的制品例如布篷(awning),用于例如帆布或帆篷中的织物,和橡胶制品例如户外席子,以及用于本披露中所引用的其它用途。这种塑料的实例是聚丙烯、聚乙烯、PVC、POM、聚砜、苯乙烯类(styrenic)、聚酰胺、聚氨酯、聚酯、聚碳酸酯、丙烯酸类、丁二烯、热塑性聚烯烃、离子聚合物、不饱和聚酯,和聚合物树脂ABS、SAN和PC/ABS的共混物。
本发明的组合物的应用的实例是施用于易受损的表面的表面涂料、防护漆、其它涂层和层压物,所述易受损的表面例如船的船体、船坞表面或水循环或流通系统中的管内侧、暴露于雨水的墙壁、淋浴的墙壁、屋顶、排水沟、池塘区域、桑拿室、暴露于潮湿环境的地板和墙壁例如地下室或车库、工具和户外设备的外壳。
例如,本发明的组合物尤其是可用于以下物质的表面上:
船体、船坞、浮标、钻探平台、压舱水罐(ballast water tank),
机器、机器零件、娱乐设施(recreational)、空调系统、离子交换剂、工业用水系统(process water system)、其它工业用水系统(industrial watersystem)、太阳能单元(solar-powered unit)、热交换器、井底水窝水泵(sumppump,油池泵)、排水系统,
盖屋顶的材料、地下室、墙壁、建筑物立面、温室、工棚(shed)、罐区、布篷、花园栅栏、木材保护(wood protection)、帐篷屋顶材料、织物、户外设备、门垫,
公共厕所、浴室、淋浴室(shower)、游泳池、桑拿室、接合物(jointing)、密封接合物、公共运输工具(public conveyance)、衣帽间等。
工业用水包括在封闭的或开放的循环系统中用于加热和冷却目的的任何工业用水蒸汽(process water stream)。
因此,本发明的具体实施方式涉及
保护塑料、涂层、家用或个人护理制剂、工业制剂或工艺流程不受微生物作用的方法,其包括向该制剂或工艺中添加有效量的本发明的聚合物或共聚物;
保护皮肤、粘膜和外皮附器不受微生物作用的方法,其包括施用包含有效量的本发明的聚合物或共聚物的制剂;
保护纸、木材、皮革、合成织物材料或天然织物材料如棉花不受微生物作用的方法,其包括加入或施用有效量的本发明的聚合物或共聚物,或包含有效量的本发明的聚合物或共聚物的组合物;
对硬表面进行清洁和灭菌的方法,其包括施用包含有效量的本发明的聚合物或共聚物的制剂;
防止制品的生物淤积的方法,其包括将本发明的抗微生物的乙烯亚胺聚合物或共聚物加到该制品或制品的表面,或者将所述抗微生物的乙烯亚胺聚合物或共聚物直接或者作为涂料或膜的一部分施用到这些表面上。
以下非限制性的实例说明本发明的一些方面。
工作实施例
实施例1
向80℃的1.7g聚乙烯亚胺聚合物的水溶液中加入6.8g苄基溴和5.6g碳酸钾在6mL甲醇和7mL水中的溶液,将混合物搅拌直到通过薄层色谱(TLC)检测到没有苄基溴为止。蒸发溶剂,用40mL乙醇将残余物回流处理15分钟,将混合物冷却并过滤,将得到的溶液浓缩,并将其真空干燥。加入40mL己烷,并将混合物加热至回流,得到分开的两相,将含有聚合物的油状层与己烷层分开,并将油状层真空蒸发至干,得到3.22g苄基取代的聚乙烯亚胺,为黄色固体。NMR分析揭示1.3-1.5当量的苄基基团/乙烯亚胺单体基团,和5-7%的副产物--苄醇。
实施例2
也通过加热回流5g聚乙烯亚胺、10g苄基溴、3.8g氢氧化钾和50ml乙醇的混合物,直到通过TLC检测到没有苄基溴为止,而使聚乙烯亚胺苄基化。过滤反应混合物,浓缩该溶液并真空干燥,得到7.8g苄基取代的聚乙烯亚胺,为黄色浆液。
实施例3
将5.6g聚乙烯亚胺和2.9g氰胺的混合物和100mL甲苯回流搅拌12小时。真空除去溶剂,得到8.4g胍取代的聚乙烯亚胺,为固体,通过13C NMR进行结构确认。
使用实施例1或2的普通方法的变化形式(variant),使聚乙烯亚胺聚合物与以下卤化物(RX)反应,得到相应的N-取代的聚合物。所述卤化物是是商业产品或容易通过已知方法制备。
实施例 RX RX/单体 取代/单体
5 0.25 0.25
RX是所用的卤化物
RX/单体是对于初始聚合物的每乙烯亚胺单体单元(-CH2-CH2-NR-)所用的卤化物的比例
取代/单体是在得到的产物中聚合物主链N原子取代的百分比
使用实施例1或2的普通方法的变化形式,使用0.25~2当量的合适卤化物(RX)/单体,用以下取代基对分子量为800、2,000和/或25,000的三种不同的聚乙烯亚胺聚合物进行取代,从而得到相应的N-取代的聚合物,并且测试所得聚合物抗以下生物的活性:细菌,大肠杆菌(e.coloi)、金黄色葡萄球菌(s.aureus);真菌,出芽短梗霉(a.pull)、绳状青霉(p.funic)、黑曲霉(a.niger),微生物粘附或生物膜积聚。每种化合物在至少一个试验中是有效的;有些在不止一种试验或者在所有的试验中都是有效的。
实施例 取代基
18
19
21
24
使用实施例1或2的普通方法的变化形式,使用0.5或1当量的合适卤化物(RX)/单体,用以下成对的取代基对聚乙烯亚胺聚合物进行取代,在每个实施例中所述取代基卤化物以相对于彼此1:1的比例加入,从而得到相应的N-取代的聚合物,并且测试所得聚合物抗以下生物的活性:细菌,大肠杆菌,金黄色葡萄球菌;真菌,出芽短梗霉,绳状青霉,黑曲霉,微生物粘附或生物膜积聚。每种化合物在至少一个试验中是有效的;有些在不止一种试验或者在所有的试验中都是有效的。
实施例 取代基1 取代基2
31 苄基
32 苄基 十二烷基
36 苄基
38 十二烷基
PEI的微生物活性:
杀菌活性(microbicidalactivity):
根据标准EN1040试验方法的微小改进(trivial modification)来测试杀菌活性。将细胞数为约107cfu/ml的细菌悬浮液与合适浓度的指定物质接触,在室温连续搅拌的条件下孵育5分钟和30分钟之后测定残余的细胞数。金黄色葡萄球菌(Staphylococcus aureus)测试为革兰氏阳性(gram+),大肠杆菌(Escherichia coli)为革兰氏阴性(gram-)有机体。将得到的细胞数减少与水对照进行比较。
杀真菌活性:
根据标准EN12175试验方法的微小改进来测试杀真菌活性。将孢子细胞数为约106cfu/ml的真菌孢子(fungal spore)悬浮液与合适浓度的指定物质接触,在室温连续搅拌的条件下孵育30分钟和60分钟之后测定残余的孢子细胞数。经测试,绳状青霉(Penicillium funiculosum)、黑曲霉(Aspergillusniger)和出芽短梗霉(Aureobasidium pullulans)为重要的霉菌菌株(moldstrain)。将得到的细胞数减少与水对照进行比较。
生物膜抑制(Biofilm inhibition):
在基于微量培养板的筛选测定中,测试化合物抑制初始阶段的生物膜形成的能力。使聚碳酸酯的标准试验样本与化合物在水或乙醇中的浓度为0.5%的溶液接触1/2小时,使化合物在针表面(pin surface)上形成膜。然后使针在室温和层流条件下干燥。在微量培养板中,使涂覆的针与细胞数为104-105cfu/ml的金黄色葡萄球菌的细菌接种物接触,历时24小时,使生物膜形成于该塑料表面上。然后在两个冲洗步骤中冲洗掉松附着的细胞,然后通过超声处理除去表面上的生物膜。将洗脱的细胞(eluted cell)转移到新微量培养板中的Caso培养液中(Caso broth),在24小时内通过测量620nm的光密度来跟踪生长情况。将结果计算为洗脱细胞在24小时孵育过程中的生长曲线,将其与未处理的样品的生长曲线进行比较。
聚乙烯亚胺样品(例如被Quab 342,Quab 426,苄基溴和己基溴所官能化)在上述的筛选测定中显示出完全的生物膜抑制。
Claims (22)
1.抗微生物的乙烯亚胺聚合物或共聚物,其中所述聚合物或共聚物主链中10-100%的氮原子被一个或多个取代基a-d取代:
a)C1-24烷基、C3-24烯基、C1-24烷基羰基或C3-24烯基羰基,所述基团是未被隔断的或被氧原子、硫原子、-SO-或-SO2-中的一个或多个隔断一次或多次,并且被一个或多个以下基团取代一次或多次:C3-6环烷基、-OR、-COOR、-COOM、-SO3M、-SO3H、膦酸基团、卤素、-CONR’R、-NR’R、膦酸根、铵根或式—L-Ar的基团,或基团-Si(G)3,其中G各自独立地为羟基、C1-4烷基或C1-4烷氧基,
条件是未被隔断的C1-24烷基不被以下基团取代:双胍、C3-6环烷基、-COOM、R是未取代的烷基的-COOR、R是H或未取代的烷基羰基的-OR或-CONR’R,除非所述C1-24烷基上也存在所述取代基中的至少一种另外的取代基;
b)下式的杂环:
其中Y和Y’独立地为N、C-R、C-OR或C-NRR’,D和D’独立地为R、-OR或-NRR’;
c)下式的基团:
其中m和n独立地为1、2、3、4、5或6;
或
d)-L-Poly,其中Poly是支化的或未支化的聚合物或低聚物,所述聚合物或低聚物选自聚醚、聚硅氧烷、苯乙烯聚合物或聚醇;
以上定义中:
R、R’和R”各自独立地为氢;
C1-24烷基、C3-24烯基、C3-6环烷基或C1-24烷基羰基,所述C1-24烷基、C3-24烯基、C3-6环烷基或C1-24烷基羰基是未被隔断的或被氧原子、硫原子、羰基、-COO-、-CONH-、-NH-、-CON(C1-8烷基)-或-N(C1-8烷基)-中的一个或多个隔断一次或多次,所述未被隔断的或被隔断的烷基、烯基、环烷基或烷基羰基是未取代的或被一个或多个以下基团取代一次或多次:卤素、-OH、C7-12芳烷基、C2-12烷基羰基、C1-24烷氧基、C2-24烷基羧基、-COOM、-CONH2、-CON(H)(C1-8烷基)、-CON(C1-8烷基)2、-NH2,
-N(H)(C1-8烷基)、-N(C1-8烷基)2、-SO3M、苯基、被一个或多个C1-8烷基取代一次或多次的苯基、萘基、被一个或多个C1-8烷基取代一次或多次的萘基、嘌呤、吡啶、嘧啶、三嗪或咪唑,所述嘌呤、吡啶、嘧啶、三嗪或咪唑是未取代的或被一个或多个C1-12烷基取代,其中所述嘌呤、吡啶、嘧啶、三嗪或咪唑是中性的或离子带电的、脒、胍、铵根、膦酸基团、膦酸根或基团,其中Q或Q’各自独立地为氢、C1-12烷基、苯基或苄基;
或者
当R和R’与氮原子连接时,R和R’与它们所连接的氮原子一起形成5-、6-或7-元环,所述环是未被隔断的或被-O-、-NH-或-N(C1-12烷基)-隔断;
L是直接键,C1-12亚烷基,所述C1-12亚烷基是未被隔断的或被一个或多个氧原子隔断,并且所述C1-12亚烷基是未取代的或被一个或多个以下基团取代一次或多次:-OH、C1-8烷基、C1-24烷氧基、C2-24烷基羧基、-NH2、-N(H)(C1-8烷基)、
-N(C1-8烷基)2或铵根;
Ar是C6-10芳族基团或饱和的或不饱和的C1-9杂环,所述芳族基团或杂环是未取代的或被一个或多个以下基团取代一次或多次:卤素、-OH、C1-24烷氧基、C2-24烷基羧基、-COOQ”、-CONH2、-CON(H)(C1-8烷基)、-CON(C1-8烷基)2、-NH2、-N(H)(C1-8烷基)、-N(C1-8烷基)2、-SO3M、SO3H、铵根、膦酸基团、膦酸根,
未取代的或被一个或多个卤素取代一次或多次的C1-24烷基、未取代的或被一个或多个C1-8烷基取代一次或多次的苯基、萘基、嘌呤、吡啶、嘧啶、三嗪或咪唑,所述嘌呤、吡啶、嘧啶、三嗪或咪唑是未取代的或被一个或多个C1-12烷基取代,其中所述嘌呤、吡啶、嘧啶、三嗪或咪唑是中性的或离子带电的;
其中Q”是氢、金属阳离子、二醇醚、聚硅氧烷、苯基或苄基;或被卤素、羟基、C1-24烷氧基或C1-12烷基中的一个或多个取代一次或多次的苯基或苄基,
M是金属阳离子或铵阳离子,
并且当所述乙烯亚胺聚合物的N原子被四取代时,它是具有相应抗衡阴离子的阳离子。
4.如权利要求2的聚合物或共聚物,其中
至少部分的所述取代基是:被卤素或铵根中的一个或多个取代一次或多次的C1-24烷基;被卤素或铵根中的一个或多个取代一次或多次的C1-24烷基羰基,或者
至少部分的所述取代基是:苄基、苯甲酰基;或被卤素、羟基、C1-12烷基、C1-12烷氧基或C1-12烷基羧基中的一个或多个取代一次或多次的苄基或苯甲酰基。
7.如权利要求1的聚合物或共聚物,其中至少部分的所述取代基选自被至少两种不同的基团取代的C1-24烷基或C1-24烷基羰基。
8.如权利要求1的聚合物或共聚物,其中至少部分的所述取代基是:
其中Y和Y’独立地为N、C-R、C-OR或C-NRR’,和
D和D’独立地为R、OR或NRR’;
尤其是,其中至少部分的所述取代基为
其中
D和D’独立地为R、OR或NRR’,其中R和R’独立地为氢;铵根;C1-24烷基、C1-24烷酰基,所述C1-24烷基或C1-24烷酰基是未取代的或被卤素、羟基或铵根中的一个或多个取代一次或多次;或者R和R’独立地为-L-Ar、或
其中L是直接键或C1-12亚烷基,和
Ar是苯基或被一个或多个以下基团取代一次或多次的苯基:卤素、-OH、C1-24烷氧基、C2-24烷基羧基、-COOH、-COOM、-CONH2、-CON(H)(C1-12烷基)、-CON(C1-12烷基)2、-NH2、-N(H)(C1-12烷基)、-N(C1-12烷基)2、铵根、C1-12烷基或烷基,所述C1-12烷基或烷基被一个或多个卤素取代一次或多次。
9.如权利要求1的聚合物或共聚物,其中至少部分的所述取代基选自-L-Poly,其中Poly为支化的或未支化的选自聚醚和聚硅氧烷的聚合物或低聚物。
10.抗微生物的乙烯亚胺聚合物或共聚物,其包括至少两种不同的如权利要求1的取代基。
11.如权利要求1的聚合物或共聚物,其中所述聚合物或共聚物主链的氮原子的一部分被两种不同的取代基取代。
12.抗微生物的乙烯亚胺聚合物或共聚物,其中所述乙烯亚胺聚合物或共聚物主链中10-99%的氮原子如权利要求1所述被取代,而所述乙烯亚胺聚合物或共聚物主链中至少1%的N原子被以下基团取代:
C1-24烷基或被-OH、-COOC1-24烷基、-COOH或-COOM取代的烷基,其中M如权利要求1中所述。
13.保护塑料、涂层、家用或个人护理制剂、工业制剂或工艺流程不受微生物作用的方法,其包括向所述制剂或工艺中添加有效量的权利要求1的聚合物或共聚物。
14.保护皮肤、粘膜和外皮附器不受微生物作用的方法,其包括施用包含有效量的权利要求1的聚合物或共聚物的制剂。
15.保护纸、木材、皮革或织物材料不受微生物作用的方法,其包括加入或施用有效量的权利要求1的聚合物或共聚物,或包含有效量的权利要求1的聚合物或共聚物的组合物。
16.包括权利要求1的聚合物或共聚物的个人护理制剂、口腔卫生制剂或洗涤和清洁制剂。
17.一种组合物,其包括权利要求1的聚合物或共聚物和另一种天然或合成的聚合物。
18.一种组合物,其包括不止一种权利要求1的聚合物或共聚物。
19.如权利要求17的组合物,其是纺织的或无纺的织物、纸制品、涂覆组合物或塑料制品。
20.对硬表面进行清洁和灭菌的方法,其包括施用包含有效量的权利要求1的聚合物或共聚物的制剂。
21.防止制品的生物淤积的方法,其包括将权利要求1的抗微生物的乙烯亚胺聚合物或共聚物加到该制品或制品的表面,或者将所述抗微生物的乙烯亚胺聚合物或共聚物直接或者作为涂料或膜的一部分施用到这些表面上。
22.权利要求1的乙烯亚胺聚合物或共聚物的用途,其作为硬表面的清洁剂和/或灭菌剂;或者作为塑料、涂层、家用或个人护理制剂、工业制剂、纸、木材、皮革、织物材料的抗微生物作用的防腐剂,或在工艺流程中作为抗微生物作用的防腐剂;或者用于制备用于保护皮肤、粘膜和/或外皮附器不受微生物作用的制剂。
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CN (1) | CN101374885A (zh) |
AU (1) | AU2007209376B2 (zh) |
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CN107200798A (zh) * | 2017-06-12 | 2017-09-26 | 厦门建霖健康家居股份有限公司 | 一种具有广谱抗菌的抗菌剂 |
CN107141474A (zh) * | 2017-07-04 | 2017-09-08 | 南开大学 | 含三氯生的聚(β‑氨酯)制备方法及在选择性杀灭口腔变形链球菌生物被膜中的应用 |
CN111345298A (zh) * | 2020-04-26 | 2020-06-30 | 深圳市润贝化工有限公司 | 一种水溶性季铵盐消毒剂 |
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JP2009524719A (ja) | 2009-07-02 |
BRPI0707305A2 (pt) | 2011-05-03 |
AU2007209376B2 (en) | 2013-02-07 |
AU2007209376A1 (en) | 2007-08-02 |
CA2636739A1 (en) | 2007-08-02 |
KR20080086520A (ko) | 2008-09-25 |
WO2007085552A3 (en) | 2008-03-27 |
WO2007085552A2 (en) | 2007-08-02 |
US20070231291A1 (en) | 2007-10-04 |
EP1984426A2 (en) | 2008-10-29 |
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