CN101233161A - 基于n-乙烯基吡咯烷酮和支化脂族羧酸的共聚物及其作为加溶剂的用途 - Google Patents
基于n-乙烯基吡咯烷酮和支化脂族羧酸的共聚物及其作为加溶剂的用途 Download PDFInfo
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- CN101233161A CN101233161A CNA2006800278788A CN200680027878A CN101233161A CN 101233161 A CN101233161 A CN 101233161A CN A2006800278788 A CNA2006800278788 A CN A2006800278788A CN 200680027878 A CN200680027878 A CN 200680027878A CN 101233161 A CN101233161 A CN 101233161A
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- vinyl
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- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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Abstract
本发明涉及基于N-乙烯基内酰胺或N-乙烯基酰胺以及支化脂族羧酸的乙烯基酯的共聚物,其制备及其作为微溶于水的物质的加溶剂的用途。
Description
本发明涉及基于N-乙烯基内酰胺或N-乙烯基酰胺和支化脂族羧酸的乙烯基酯的共聚物,涉及该共聚物的制备,及其作为微溶于水的物质的加溶剂的用途。此外,本发明涉及在人、动物和植物中应用的相应制剂。
当制备生物活性物质的均相制剂时,对疏水性物质,即微溶于水的物质的加溶具有非常大的实用意义。
加溶可以理解成,使在某些溶剂,尤其在是水中不溶或微溶的物质通过界面活性化合物,即加溶剂而可溶。这样的加溶剂可将水溶性差或水不溶性的物质转化成澄清,至多乳白色的水溶液,而在该过程中该物质的化学结构没有发生变化(参见Rmpp Chemie Lexikon,第9版,第5卷,第4203页,Thieme Verlag,Stuttgart,1992)。
制备的加溶物因以下事实而值得注意,即水溶性差或水不溶性的物质以胶态溶解的形式存在于在水溶液中形成的表面活性物质的分子缔合物,即所谓的胶束中。得到的溶液是稳定的单相体系,其看起来是澄清至乳白色的,且可以不输入能量而制备。
加溶剂可以例如通过使配制剂透明来改进化妆品配制剂和食品制剂的外观。此外,在药物制剂的情况下,也可以通过使用加溶剂提高药剂的生物利用率,由此提高药剂的效果。
用于药物药剂和化妆品活性成分的加溶剂主要是表面活性剂,如乙氧基化(氢化)蓖麻油、乙氧基化失水山梨糖醇脂肪酸酯或乙氧基化羟基硬脂酸。
然而,迄今为止所用的上述加溶剂具有很多与应用有关的缺点。
因此,例如它们的肠胃外施用伴随着组胺的释放和由此导致的血压下降(Lorenz et al.Agents and Actions,第12卷,1/2,1982)。
已知的加溶剂对于一些微溶的药剂如克霉唑仅具有小的加溶效果。
界面活性化合物经常具有高溶血活性,这阻止了其在药物领域,尤其是在肠胃外给药物质中的应用。
加溶剂的另一个期望的要求是与微溶物质形成所谓的“固体溶液”的能力。术语“固体溶液”是指物质在固体基质例如聚合物基质中呈分子分散分布的状态。这样的固体溶液例如当以微溶的活性成分的固体药物给药形式使用时,会导致活性成分的释放改进。这样的固体溶液的一个重要的要求是即使经长时间储存时也是稳定的,即活性成分不应结晶出。
当形成固体溶液时,除了加溶剂形成固体溶液的基本能力以外,加溶剂的吸湿性也发挥重要的作用。从周围的空气中吸收了太多水的加溶剂会导致固体溶液的潮解,从而导致活性成分的不期望的结晶。过分的吸湿性在得到给药形式的加工中也会产生问题。
US 4,432,881描述了一种分子量为200000-5000000的疏水改性聚丙烯酸,其通过丙烯酸与相应的N-烷基丙烯酰胺或丙烯酸酯共聚得到。得到的聚合物作为可分散的疏水性增稠剂使用。
US 4,395,524描述了疏水性组分(如丙烯酰胺、丙烯酸、N-乙烯基吡咯烷酮等)与N-烷基丙烯酰胺的共聚。以此方式得到的分子量为30000-2000000的聚合物用作增稠剂、沉降稳定剂或分散剂。
EP-A-0 268 164描述了单烯属不饱和酸和单烯属不饱和酸的烷基酯的共聚物稳定O/W乳液的用途。
EP-A 876 819描述了至少60重量%的N-乙烯基吡咯烷酮和具有长链烷基的酰胺或酯的共聚物的用途。
EP-A 948 957描述了单烯属不饱和羧酸如丙烯酸与疏水改性共聚单体如具有C8-C30烷基的不饱和羧酸的N-烷基-或N,N-二烷基酰胺的共聚物的用途。
迄今为止所知的聚合物加溶剂具有的缺点在于它们不能形成稳定的固体溶液,或者太疏水。此外,在含水体系的加溶方面,它们仍然具有改进的空间。
本发明的目的在于,提供用于药物、化妆品、食品和农业技术应用的新型加溶剂。
该目的通过包含如下组分的共聚物实现:
a)60-99重量%的至少一种选自N-乙烯基内酰胺和N-乙烯基酰胺的单体,
b)1-40重量%的至少一种选自脂族支化C8-C30羧酸的乙烯基酯的单体,
c)0-30重量%的乙酸乙烯基酯,
d)0-39重量%的至少一种其他可自由基共聚的单体,
其中各组分的重量%数值加起来是100%,且条件是b)和c)的量之和是总量的1-40重量%。
此外,本发明涉及上述共聚物作为用于微溶于水的物质的加溶剂的用途,以及相应的制剂。
合适的单体a)是N-乙烯基内酰胺,如N-乙烯基吡咯烷酮、N-乙烯基哌啶酮和N-乙烯基己内酰胺,或N-乙烯基酰胺,如N-甲基-N-乙烯基乙酰胺、N-乙烯基乙酰胺和N-乙烯基甲酰胺。
优选的单体a)是N-乙烯基吡咯烷酮和N-乙烯基己内酰胺。
单体a)在共聚物中的比例优选在70-95重量%的范围内,尤其优选在74-94重量%的范围内。
根据本发明,合适的疏水性组分b)是脂族支化,尤其是饱和的支化C8-C30羧酸的乙烯基酯。就此而言合适的尤其是,具有至少8个碳原子的所谓的versatic酸的乙烯基酯。该versatic酸是具有叔位羧基的高度支化的饱和单羧酸,其中α-支化点带有至少一个甲基,并且所述数值是指碳原子总数,这意味着,versatic 8例如是2,2-二甲基己酸。合适的酸还有例如,2,2-二甲基庚酸、2-乙基-2-甲基庚酸、2,2-二甲基辛酸、2-乙基-2-甲基辛酸或2,2-二甲基壬酸,优选versatic 9酸和versatic 10酸的乙烯基酯。这样的versatic酸的乙烯基酯是市售的。
疏水性单体结构单元b)在共聚物中的比例优选在5-30重量%的范围内,尤其优选10-20重量的范围内。
作为单体c),乙酸乙烯基酯的用量为至多30重量%。单体b)和c)的量之和优选为8-30重量%,尤其优选10-30重量%。
组分a)-c)之和尤其优选为100重量%。
此外,该共聚物可以含有下列可自由基共聚的单体d):
单烯属不饱和C3-C8羧酸的N-C8-C30烷基取代酰胺或N,N-C8-C30二烷基取代酰胺,其中烷基是具有8-30个,优选8-18个碳原子的直链或支化的脂族或脂环族烷基。这里,合适的具有3-8个碳原子的单烯属不饱和羧酸是丙烯酸、甲基丙烯酸、二甲基丙烯酸、乙基丙烯酸、马来酸、柠康酸、亚甲基丙二酸、烯丙基乙酸、乙烯基乙酸、巴豆酸、富马酸、中康酸和衣康酸,优选丙烯酸、甲基丙烯酸、马来酸或上述羧酸的混合物。
优选的酰胺化共聚单体例如是,N-硬脂基丙烯酰胺、N-硬脂基甲基丙烯酰胺、N-(1-甲基)十一烷基丙烯酰胺、N-(1-甲基)十一烷基甲基丙烯酰胺、N-十二烷基丙烯酰胺、N-十二烷基甲基丙烯酰胺、N-辛基丙烯酰胺、N-辛基甲基丙烯酰胺、N,N-二辛基丙烯酰胺、N,N-二辛基甲基丙烯酰胺、N-鲸蜡基丙烯酰胺、N-鲸蜡基甲基丙烯酰胺、N-十二烷基丙烯酰胺、N-十二烷基甲基丙烯酰胺、N-肉豆蔻基丙烯酰胺、N-肉豆蔻基甲基丙烯酰胺、N-(2-乙基)己基丙烯酰胺、N-(2-乙基)己基甲基丙烯酰胺。
在马来酸酐作为共聚单体的情况下,它可以以类似聚合物的方式通过开环与N-烷基胺反应,从而得到相应的酰胺。
可使用的额外共聚单体d)是与C8-C30醇,优选C8-C18醇形成的单烯属不饱和C3-C8羧酸酯。
就此而言尤其重要的是,与链长为8-18个碳原子的脂肪醇形成的丙烯酸酯和甲基丙烯酸酯,其中烷基可以是支化的或未支化的。
这里尤其可以提及:丙烯酸辛酯、丙烯酸2-乙基己酯、丙烯酸壬酯、丙烯酸癸酯、丙烯酸月桂基酯、丙烯酸肉豆蔻基酯、丙烯酸鲸蜡基酯、丙烯酸硬脂基酯、丙烯酸油基酯、丙烯酸山萮基酯、甲基丙烯酸辛酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸壬酯、甲基丙烯酸癸酯、甲基丙烯酸月桂基酯、甲基丙烯酸肉豆蔻基酯、甲基丙烯酸鲸蜡基酯、甲基丙烯酸硬脂基酯、甲基丙烯酸油基酯、甲基丙烯酸山萮基酯、丙烯酸叔丁基环己基酯。
作为另一些额外的组分d),可以使用长链脂族饱和或不饱和未支化的C8-C30羧酸的乙烯基酯,所述羧酸例如是,辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸、山萮酸、二十四烷酸、蜡酸和蜂花酸。
此外,可以共聚作为单体d)的C8-C30烷基乙烯基醚,优选C8-C18烷基乙烯基醚。可以提及的优选的乙烯基醚的烷基是支化或未支化的C8-C18烷基链,例如,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、正十五烷基、正十六烷基、正十七烷基和正十八烷基。
合适的额外的自由基共聚的单体d)是:
具有3-8个碳原子的单烯属不饱和羧酸例如是,丙烯酸、甲基丙烯酸、二甲基丙烯酸、乙基丙烯酸、马来酸、柠康酸、亚甲基丙二酸、烯丙基乙酸、巴豆酸、富马酸、中康酸和衣康酸。
从这组单体中,优选使用丙烯酸、甲基丙烯酸或上述羧酸的混合物。
单烯属不饱和羧酸可以在共聚中作为游离酸、作为酸酐,以及以部分或全部被中和的形式使用。
为了中和上述羧酸,优选使用碱金属或碱土金属碱、氨或胺,优选氢氧化钠溶液、氢氧化钾溶液、碳酸钠、碳酸钾、碳酸氢钠、氧化镁、氢氧化钙、氧化钙、气态或含水的氨、三乙胺、乙醇胺、二乙醇胺、三乙醇胺、吗啉、二亚乙基三胺或四亚乙基五胺。
待用于聚合的其他合适的共聚单体d)例如是,0-5摩尔%量的短链C1-C4醇的单烯属不饱和C3-C8羧酸酯或腈。
可以提及的实例是:丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、丙烯酸羟乙基酯、丙烯酸羟丙基酯、丙烯酸羟丁基酯、甲基丙烯酸羟乙基酯、甲基丙烯酸羟丙基酯、丙烯酸羟基异丁基酯、甲基丙烯酸羟基异丁基酯、马来酸单甲酯、马来酸二甲酯、马来酸单乙酯、马来酸二乙酯、丙烯酸2-乙基己酯、甲基丙烯酸2-乙基己酯、N-二甲基丙烯酰胺、N-叔丁基丙烯酰胺、丙烯腈、甲基丙烯腈、丙烯酸二甲基氨基乙基酯、丙烯酸二乙基氨基乙基酯、甲基丙烯酸二甲基氨基乙基酯、甲基丙烯酸二乙基氨基乙基酯,以及上述后提到的单体与羧酸或无机酸的盐,以及季铵化产物。
其他合适的单体d)例如是:
-丙烯酰胺基乙醇酸、乙烯基磺酸、烯丙基磺酸、甲代烯丙基磺酸、苯乙烯磺酸、丙烯酸(3-磺基丙基)酯、甲基丙烯酸(3-磺基丙基)酯以及丙烯酰胺基甲基丙磺酸;
-含有膦酸基团的单体,如乙烯基膦酸、烯丙基膦酸和丙烯酰胺基甲烷丙烷膦酸。
当然也可以使用上述单体的混合物。
优选的单体d)是丙烯酸、甲基丙烯酸、甲基丙烯酸甲酯、丙烯酸乙酯、月桂酸乙烯基酯、甲基丙烯酸硬脂基酯和丙烯酸月桂基酯。
单体结构单元d)为在共聚物中的比例优选在0-5重量%的范围内,尤其优选0重量%。
根据本发明使用的共聚物可以具有10-200,优选为15-100,尤其优选20-50的K值,按照Fikentsher在乙醇中以1重量%浓度测量。
共聚物通过自由基聚合相应的单体制备。
制备通过已知的方法进行,如溶液聚合、沉淀聚合,或通过使用在聚合条件下形成自由基的化合物进行反向悬浮聚合进行。
聚合温度通常在30-200℃,优选在40-110℃的范围内。合适的引发剂例如是,偶氮和过氧化合物,以及常规的氧化还原引发剂体系如过氧化氢与还原化合物的组合,还原化合物例如为亚硫酸钠、亚硫酸氢钠、甲醛合次硫酸氢钠和肼。
所用的反应介质是单体可溶于其中的任何常规溶剂。优选使用水或醇溶剂,例如甲醇、乙醇、正丙醇或异丙醇或这些醇与水的混合物。
为了确保反应产生均匀产物,有利地是分开地向反应溶液中供入单体和引发剂。这例如可以以各反应物的分开进料的形式进行。
如果要建立较低的分子量,也可以在常规调节剂的存在下进行聚合。
得到的有机溶液的固体含量通常是20-60重量%,尤其是25-40重量%。
用于聚合的非水溶剂然后可以通过蒸汽蒸馏移除,并被水代替。
共聚物的水溶液可以通过各种干燥方法,例如,喷雾干燥、流化喷雾干燥、转鼓式干燥或冷冻干燥,转变成粉末形式,可以通过再分散在水中而从该粉末形式再次制备水溶液。
应用:
根据本发明使用的共聚物原则上可以在其中不溶或仅微溶于水的物质在含水制剂中使用,或者在含水介质中发挥它们的作用的所有领域中使用。因此,共聚物用作微溶于水的物质,尤其是生物活性物质的加溶剂。
根据本发明,术语“微溶于水”也包括实质上不溶的物质,是指对于20℃下所述物质在水中的溶液,每克物质需要至少30-100g的水。在实质上不溶的物质的情况下,每克物质需要至少10000g水。
对本发明而言,微溶于水的生物活性物质理解成用于人和动物的药物活性成分、化妆品或农业化学活性成分或食品添加物或饮食活性成分。
此外,合适的待加溶的微溶物质还有染料,如无机或有机颜料。
通过本发明,提供了尤其是用作药物和化妆品制剂以及食品制剂的加溶剂的两亲化合物。它们具有使下述物质溶解增加的性质,所述物质例如为在药物和化妆品领域中的微溶活性成分、微溶的食品添加物如维生素和类胡萝卜素,还有用于作物保护组合物中的微溶活性成分以及兽药活性成分。
令人惊奇地是,在本发明化合物的情况下,已发现了对于药物和化妆品活性成分的良好的加溶能力。此外,通过本发明的化合物获得了用途,特征在于在对皮肤和粘膜进行肠胃外的、口服和局部应用后,溶血速率非常低,且具有无副反应的相容性。尤其是,所述化合物没有由于与血细胞膜的相互作用而导致的二级反应。在肠胃外应用后,没有释放或仅微微地释放组胺。如果需要的话,可以调节加溶剂的分子量使加溶剂通过肾脏。用于化妆品的加溶剂:
根据本发明,所述共聚物可以在化妆品配制剂中用作加溶剂。例如,它们适合作为用于化妆品油的加溶剂。它们具有对脂肪和油或者精油的良好的加溶能力,所述脂肪和油例如为花生油、霍霍巴油、椰子油、杏仁油、橄榄油、棕榈油、蓖麻油、大豆油或小麦胚芽油,所述精油例如为矮松油、熏衣草油、迷迭香油、云杉针油、松针油、桉树油、薄荷油、鼠尾草油、佛手油、松节油(terpentine oil)、蜂花油、鼠尾草油、刺柏油、柠檬皮油、茴香油、小豆蔻油、薄荷油、樟脑油等,或这些油的混合物。
此外,本发明聚合物还可以用作用于不溶或微溶于水的UV吸收剂的加溶剂,所述UV吸收剂例如是,2-羟基-4-甲氧基二苯甲酮(UvinulM 40,BASF)、2,2’,4,4’-四羟基二苯甲酮(UvinulD 50)、2,2’-二羟基-4,4’-二甲氧基二苯甲酮(UvinulD49)、2,4-二羟基二苯甲酮(Uvinul400)、2-氰基-3,3-二苯基丙烯酸2’-乙基己基酯(UvinulN 539)、2,4,6-三苯氨基对(羰基-2’-乙基己基-1’-氧-)-1,3,5-三嗪(UvinulT 150)、3-(4-甲氧基苯亚甲基)樟脑(Eusolex6300,Merck)、N,N-二甲基-4-氨基苯甲酸2-乙基己基酯(Eusolex6007)、3,3,5-三甲基环己基水杨酸酯、4-异丙基二苯甲酰基甲烷(Eusolex8020)、对甲氧基肉桂酸2-乙基己基酯和对甲氧基肉桂酸2-异戊基酯,以及它们的混合物。
因此,本发明还提供了含有至少一种具有开始所指出的组成的本发明共聚物作为加溶剂的化妆品制剂。优选那些除了加溶剂以外,还含有一种或多种微溶的化妆品活性成分,例如上述的油或UV吸收剂的制剂。
这些配制剂是基于水或水和醇的加溶物。根据本发明的加溶剂相对于微溶的化妆品活性成分以0.2∶1-20∶1,优选1∶1-15∶1,尤其优选2∶1-12∶1的比例使用。
取决于活性成分,根据本发明的加溶剂在化妆品制剂中的含量为1-50重量%,优选3-40重量%,尤其优选5-30重量%的范围内。
此外,可以向该配制剂中加入其他辅助剂,例如非离子性、阳离子性或阴离子性表面活性剂,如烷基多苷、脂肪醇硫酸酯、脂肪醇醚硫酸酯、链烷磺酸酯、脂肪醇乙氧化物、脂肪醇磷酸酯、烷基甜菜碱、失水山梨糖醇酯、POE失水山梨糖醇酯、糖脂肪酸酯、脂肪酸聚甘油酯、脂肪酸部分甘油酯、脂肪酸羧酸酯、脂肪醇磺基琥珀酸酯、脂肪酸肌氨酸酯、脂肪酸羟乙基磺酸酯、脂肪酸牛磺酸酯、柠檬酸酯、硅氧烷共聚物、脂肪酸聚二醇酯、脂肪酸酰胺、脂肪酸链烷醇酰胺、季铵化合物、烷基酚乙氧化物、脂肪胺乙氧化物,共溶剂如乙二醇、丙二醇、甘油等。
可以加入的其他组分是天然或合成化合物,如羊毛脂衍生物、胆固醇衍生物、肉豆蔻酸异丙酯、棕榈酸异丙酯、电解质、染料、防腐剂、酸类(如乳酸、柠檬酸)。
这些配制剂例如用于浴用添加制剂(如浴油)、剃须后用品、面部滋补剂、头发滋补剂、古龙香水、化妆水,以及防晒组合物中。此外,它们还用于口部护理,例如牙膏、漱口水或唇膏中。
加溶方法的描述:
在用于化妆品配制剂的加溶物的制备中,根据本发明的共聚物可以以100%浓度的物质使用,或优选作为水溶液使用。
通常,将加溶剂溶解在水中,并与在每种情况下使用的微溶的化妆品活性成分剧烈混合。
然而,也可以将加溶剂与在每种情况下使用的微溶的化妆品活性成分剧烈混合,然后在连续搅拌下加入软化水。
用于药物应用的加溶剂:
本发明的共聚物同样适于用作任何类型的药物制剂中的加溶剂,所述药物制剂的特征在于可以含有一种或多种在水中不溶或微溶的药剂、以及维生素和/或类胡萝卜素。尤其是,它们是用于口服应用或尤其优选用于肠胃外应用的水溶液或加溶物,例如是用于静脉、肌肉、皮下、腹膜内应用的注射溶液。
此外,本发明的共聚物适于以口服给药形式,如片剂、胶囊剂、散剂、溶液使用。这里,它们可以使微溶药剂具有增加的生物利用率。
在肠胃外应用的情况下,除了加溶物以外,还可以使用乳液,例如脂肪乳液。本发明的共聚物也适合该目的,从而加工微溶的药剂。
上述类型的药物配制剂可以通过常规方法加工本发明的共聚物和药物活性成分而得到,其中使用已知或新的活性成分。
根据本发明的应用可以额外包括药物辅助剂和/或稀释剂。作为辅助剂特别提及的是共溶剂、稳定剂、防腐剂。
所用的药物活性成分是在水中不溶或微溶的物质。根据DAB 9(德国药典),药物活性成分的溶解性分类如下:微溶(在30-100份溶剂中溶解);微溶(在100-1000份溶剂中溶解);实质上不溶(在多于10000份溶剂中溶解)。这里的活性成分可以来自任何适应症领域。
这里可以提及的实例是,苯并二氮类,抗高血压药,维生素,细胞生长抑制剂,尤其是紫杉酚,***,精神安定药,抗抑郁药,抗生素,抗真菌药,杀真菌药,化学治疗药,泌尿***药,血小板聚集抑制剂,磺胺类药,解痉药,激素,免疫球蛋白,血清,甲状腺治疗药,精神药理学药,抗震颤麻痹药和其他抗运动过度药,眼药,神经病制剂,钙代谢调节剂,肌肉松弛药,麻醉剂,抗血脂药,肝治疗药,冠状疾病治疗药,强心药,免疫治疗药,调节肽及其抑制剂,催眠药,镇静药,妇科试剂,抗痛风药,纤蛋白溶解剂,酶制剂和运输蛋白,酶抑制剂,催吐药,循环促进剂,利尿药,诊断用药,肾上腺皮质激素类,拟胆碱药,胆管治疗药,平喘药,支气管药(broncholytic),β-受体阻断药,钙拮抗药,ACE抑制剂,抗动脉硬化药,抗炎药,抗凝血药,抗低血压药,抗低血糖药,抗高渗药,抗纤维蛋白溶解药,抗癫痫药,止吐药,解毒药,抗糖尿病药,抗心率失常药,抗贫血药,抗过敏药,驱肠虫药,镇痛药,回苏药,醛固酮拮抗药,以及减食疗法剂。
一种可能的制备方案是将加溶剂溶解在水相中,如果合适的话在温和的加热下进行,然后将活性成分溶解在加溶剂的水溶液中。同样也可以使加溶剂和活性成分同时溶解在水相中。
根据本发明的共聚物作为加溶剂的应用也可以例如通过将活性成分分散在加溶剂中,如果合适的话同时加热,并且在搅拌下将其与水混合来进行。
本发明由此还提供了含有至少一种根据本发明的共聚物作为加溶剂的药物制剂。优选那些除了加溶剂以外,还含有不溶或微溶于水的药物活性成分(例如来自上述适应症领域)的制剂。
在上述的药物制剂中,尤其优选可肠胃外应用的制剂。
取决于活性成分,根据本发明的加溶剂在药物制剂中的含量在1-50重量%,优选3-40重量%,尤其优选5-30重量%的范围内。
用于食品制剂的加溶剂:
除了在化妆品和药物中应用外,根据本发明的共聚物也适合在食品领域中用作不溶或微溶于水的营养物、辅助剂或添加剂(例如脂溶性维生素或类胡萝卜素)的加溶剂。可以提及的实例是被类胡萝卜素着色的澄清饮料。用于作物保护制剂的加溶剂:
根据本发明的共聚物在农业化学品中作为加溶剂的应用可以尤其包括含有农药、除草剂、杀真菌剂或杀虫剂的配制剂,特别是还有那些作为喷雾混合物或浇灌混合物使用的作物保护组合物的制剂。
根据本发明的水溶性共聚物的特征在于尤其好的加溶效果。它们也出人意料地适于制备稳定的固体溶液。
在下面的实施例中,更加详细地说明了根据本发明的共聚物的制备和应用。
实施例
在下面的实施例中使用缩写VEOVA代表versatic酸的乙烯基酯。缩写后的数值是指碳原子数。单体是市售的。
为了制备聚合物,使用下面的设备:
配备有水浴、桨式搅拌器和温度计的2L HWS锅。该HWS锅具有用于3种进料的连接器、回流冷凝器、以及用于引入氮气或蒸汽的入口管。
实施例1
N-乙烯基吡咯烷酮/乙酸乙烯基酯/VEOVA 9(重量比70/15/15)的共聚物的制备
量,g | 物质 | |
初始加料 | 12.0 | 异丙醇 |
70.0 | 部分进料1 | |
1.0 | 部分进料2 | |
进料1 | 222.0 | 异丙醇 |
320.0 | 乙烯基吡咯烷酮 | |
75.0 | VEOVA 9 | |
75.0 | 乙酸乙烯基酯 | |
进料2 | 85.4 | 异丙醇 |
4.5 | 过新戊酸叔丁酯,浓度75% | |
进料3 | 25.6 | 异丙醇 |
30.0 | 乙烯基吡咯烷酮 |
在所述设备中,以180rpm的设定混合12g异丙醇和70g进料1。将温和的氮气流连续通过该设备。同时将***加热至内部温度为70℃。在68℃下加入部分进料2(1.0g),并使混合物聚合10分钟。
然后开始进料1和进料2。经4小时计量加入进料1。经5小时计量加入37g进料2。当进料1完成时,经1小时计量加入进料3。当已加入部分进料2时,将混合物在70℃下进行额外1小时的后聚合。然后将混合物加热至内部温度为75℃。与加热操作平行地开始进料2(剩余量52g),并经2小时计量加入。在进料2结束时,将混合物在75℃下进行额外2小时的后聚合。
然后加入400g完全软化水,并在聚合物溶液中通入3小时蒸汽。
这得到了固体含量为32重量%的黄色粘性溶液。K值是33(在乙醇中以1重量%浓度测量)。
实施例2
N-乙烯基吡咯烷酮/VEOVA 9(重量比80/20)的共聚物的制备
量,g | 物质 | |
初始加料 | 12.0 | 异丙醇 |
78.0 | 部分进料1 | |
5.0 | 部分进料2 | |
进料1 | 222.0 | 异丙醇 |
400.0 | 乙烯基吡咯烷酮 | |
100.0 | VEOVA 9 | |
进料2 | 100.0 | 异丙醇 |
4.5 | 过新戊酸叔丁酯,浓度75% |
在所述设备中,以180rpm的设定混合12g异丙醇和78g进料1。将温和的氮气流连续通过该设备。同时将***加热至内部温度为75℃。在73℃下加入部分进料2(5.0g),并使混合物聚合10分钟。
然后开始进料1和进料2。经4小时计量加入进料1,并经6小时计量加入进料2。然后将混合物进行额外2小时的后聚合。
然后加入400g完全软化水,并在聚合物溶液中通入约3小时蒸汽。
这得到了固体含量为27重量%的黄色粘性溶液。K值是35(在乙醇中以1重量%浓度测量)。
实施例3
N-乙烯基吡咯烷酮/VEOVA 9(重量比90/10)的共聚物的制备
量,g | 物质 | |
初始加料 | 12.0 | 异丙醇 |
78.0 | 部分进料1 | |
5.0 | 部分进料2 | |
进料1 | 222.0 | 异丙醇 |
450.0 | 乙烯基吡咯烷酮 | |
50.0 | VEOVA 9 | |
进料2 | 100.0 | 异丙醇 |
4.5 | 过新戊酸叔丁酯,浓度75% |
在所述设备中,以180rpm的设定混合12g异丙醇和78g进料1。将温和的氮气流连续通过该设备。同时将***加热至内部温度为75℃。在73℃下加入部分进料2(5.0g),并使混合物聚合10分钟。
然后开始进料1和进料2。经4小时计量加入进料1,并经6小时计量加入进料2。然后将混合物进行额外2小时的后聚合。
然后加入400g完全软化水,并在聚合物溶液中通入约3小时蒸汽。
这得到了固体含量为34重量%的黄色粘性溶液。
K值是35(在乙醇中以1重量%浓度测量)。
实施例4
N-乙烯基吡咯烷酮/N-乙烯基己内酰胺/VEOVA 10(重量比70/20/10)的共聚物的制备
量,g | 物质 | |
初始加料 | 12.0 | 异丙醇 |
70.0 | 部分进料1 | |
1.0 | 部分进料2 | |
进料1 | 222.0 | 异丙醇 |
320.0 | 乙烯基吡咯烷酮 | |
75.0 | VEOVA 9 | |
75.0 | 乙酸乙烯基酯 | |
进料2 | 85.4 | 异丙醇 |
4.5 | 过新戊酸叔丁酯,浓度75% | |
进料3 | 25.6 | 异丙醇 |
30.0 | 乙烯基吡咯烷酮 |
在所述设备中,以180rpm的设定混合12g异丙醇和70g进料1。将温和的氮气流连续通过该设备。同时将***加热至内部温度为70℃。在68℃下加入部分进料2(1.0g),并使混合物聚合10分钟。
然后开始进料1和进料2。经4小时计量加入进料1,经5小时计量加入37g进料2。在进料1结束时,经1小时计量加入进料3。当完成所述部分进料2时,将混合物在70℃下进行额外1小时的后聚合。然后将混合物加热至内部温度为75℃。与加热操作平行地,开始进料2(剩余量52g),并经2小时计量加入。在进料2结束时,将混合物在75℃下进行额外2小时的后聚合。
然后加入400g完全软化水,并在聚合物溶液中通入约3小时蒸汽。
这得到了固体含量为32重量%的黄色粘性溶液。
K值是47(在乙醇中以1重量%浓度测量)。
过新戊酸叔丁酯:在脂族混合物中,75重量%的活性物,
TBPPI-75-AL,来自Degussa,82049 Pullach/德国
实施例试验的表格
单体a) | 单体a) | 单体b) | 单体c) | 单体d) | |
实施例1 | 70 VP | 15VEOVA-9 | 15 VAc |
实施例2 | 80 VP | 20VEOVA-9 | |||
实施例3 | 90 VP | 10VEOVA-9 | |||
实施例4 | 70 VP | 20 VCap | 10VEOVA-10 | ||
实施例5 | 50 VP | 20 VCap | 10VEOVA-9 | 20 VAc | |
实施例6 | 40 VP | 40 VCap | 10VEOVA-9 | 10 VAc | |
实施例7 | 50 VP | 30 VIMA | 20VEOVA-9 | ||
实施例8 | 92 VP | 8VEOVA-10 | |||
实施例9 | 85 VP | 10VEOVA-9 | 5 LA |
与实施例1-4类似地制备根据实施例5-9的聚合物。
用于组成的所有数值为重量%。
VP N-乙烯基吡咯烷酮
VAc 乙酸乙烯基酯
VEOVA-9 versatic酸9的乙烯基酯
VEOVA-10 versatic酸10的乙烯基酯
VCap 乙烯基己内酰胺
VIMA N-乙烯基-N-甲基乙酰胺
LA 丙烯酸月桂基酯
固体溶液的制备:一般程序
为了制备聚合物/活性成分混合物,将活性成分和聚合物以重量比1∶1(在每种情况下2g)称入合适的玻璃容器中,然后加入16ml的二甲基甲酰胺作为溶剂。在磁力搅拌器上将该混合物在20℃搅拌24小时。然后使用120μm的刮刀将溶液移出至玻璃板上。将其在通风橱中于室温干燥0.5小时,然后在50℃、10毫巴的干燥箱中额外干燥0.5小时以除去所有的溶剂。然后目视评估试样。如果7天后活性成分没有结晶出,则形成了稳定的固体溶液。
共聚物根据 | 卡马西平(Carbamazepine) | ***(Estradiol) | 克霉唑(Clotrimazol) |
实施例1 | 固体溶液 | 固体溶液 | 固体溶液 |
实施例2 | 固体溶液 | 固体溶液 | 固体溶液 |
实施例3 | 固体溶液 | 固体溶液 | 固体溶液 |
实施例4 | 固体溶液 | 固体溶液 | 固体溶液 |
实施例5 | 固体溶液 | 固体溶液 | 固体溶液 |
加溶物的制备
将2g共聚物称入烧杯中,然后在每种情况下将一种药剂称入如下的混合物中以得到超饱和溶液。(如果称入的物质溶解在介质中,则增加起始重量直至沉降形成。)
活性成分 | 起始重量[g] |
17-β-*** | 0.25 |
吡罗昔康(Piroxicam) | 0.25 |
卡马西平 | 0.35 |
然后加入pH7.0的磷酸酯缓冲液,直至加溶剂和磷酸酯缓冲液以重量比1∶9存在。使用磁力搅拌器,将该混合物在20℃下搅拌72小时。然后接着经过至少1小时的静置时间。过滤混合物后,进行光度法测量,测定活性成分的含量。
结果:加溶的活性成分的含量[g/100ml]
共聚物根据 | 卡马西平 | *** | 吡罗昔康 |
实施例1 | 0.21 | 0.07 | 0.53 |
实施例2 | 0.17 | 0.08 | 0.54 |
实施例3 | 0.19 | 0.04 | 0.48 |
实施例4 | 0.21 | 0.09 | 0.50 |
实施例5 | 0.30 | 0.07 | 0.52 |
Claims (29)
1.一种共聚物,含有:
a)60-99重量%的至少一种选自N-乙烯基内酰胺和N-乙烯基酰胺的单体,
b)1-40重量%的至少一种选自脂族支化C8-C30羧酸的乙烯基酯的单体,
c)0-30重量%的乙酸乙烯基酯,
d)0-39重量%的至少一种其他可自由基共聚的单体,
其中各组分a)至d)的重量%数值加起来是100%,且条件是b)和c)的量之和是总量的1-40重量%。
2.根据权利要求1的共聚物,其中共聚物含有:
a)70-95重量%的至少一种选自N-乙烯基内酰胺和N-乙烯基酰胺的单体,
b)5-30重量%的至少一种选自脂族支化C8-C30羧酸的乙烯基酯的单体,
c) 0-25重量%的乙酸乙烯基酯,
d)0-25重量%的至少一种其他可自由基共聚的单体。
3.根据权利要求1或2的共聚物,其中共聚物具有10-200的K值。
4.根据权利要求1-3中任一项的共聚物,其中单体a)选自N-乙烯基吡咯烷酮、N-乙烯基己内酰胺。
5.根据权利要求1-3中任一项的共聚物,其中共聚物含有versatic酸的乙烯基酯作为单体b)。
6.根据权利要求1-4中任一项的共聚物,其中共聚物含有C9-C10versatic酸的乙烯基酯作为单体b)。
7.根据权利要求1-5中任一项的共聚物,其中b)和c)之和是8-30重量%。
8.根据权利要求1-6中任一项的共聚物,其中共聚物含有至多5重量%的单体d)。
9.根据权利要求1-7中任一项的共聚物,其中单体a)至c)之和是100重量%。
10.根据权利要求1-8中任一项的共聚物,其中共聚物含有N-乙烯基吡咯烷酮或N-乙烯基己内酰胺或其混合物作为单体a)。
11.根据权利要求1-9中任一项的共聚物,通过自由基引发聚合单体a)至d)得到。
12.根据权利要求1-11中任一项的共聚物作为微溶于水的物质的加溶剂的用途。
13.根据权利要求12的用途,用于微溶于水的生物活性物质。
14.根据权利要求12或13的用途,用于制备治疗疾病的药物制剂。
15.根据权利要求12或13的用途,用于化妆品制剂。
16.根据权利要求12或13的用途,用于农业化学制剂。
17.根据权利要求12或13的用途,用于食品添加物或饮食试剂。
18.根据权利要求12的用途,用于食品。
19.根据权利要求12的用途,用于染料制剂。
20.一种微溶于水的物质的制剂,含有根据权利要求1-11中任一项的共聚物作为加溶剂。
21.根据权利要求20的制剂,含有生物活性物质作为微溶于水的物质。
22.根据权利要求20或21的制剂,含有药物活性成分作为微溶于水的生物活性物质。
23.根据权利要求22的制剂,呈可肠胃外应用的给药形式。
24.根据权利要求20或21的制剂,含有化妆品活性成分作为微溶于水的生物活性物质。
25.根据权利要求20或21的制剂,含有农业化学活性成分作为微溶于水的生物活性物质。
26.根据权利要求20或21的制剂,含有食品添加物或饮食活性成分作为微溶于水的生物活性物质。
27.根据权利要求20的制剂,含有染料作为微溶于水的物质。
28.一种制备根据权利要求1-11中任一项的共聚物的方法,其中将组分a)至c)进行自由基聚合。
29.根据权利要求28的方法,其中分开地将组分a)-c)供给聚合反应。
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WO2013037382A1 (en) * | 2011-09-12 | 2013-03-21 | Oxea Gmbh | Vinyl acetate/vinyl 3,5,5-trimethylhexanoate copolymer binder resins |
US20130123104A1 (en) * | 2011-09-19 | 2013-05-16 | Rhodia Operations | Adjuvant Compositions, Agricultural Pesticide Compositions, and Methods for Making and Using Such Compositions |
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