CN101283008A - 基于n-乙烯基已内酰胺的共聚物及其作为增溶剂的用途 - Google Patents
基于n-乙烯基已内酰胺的共聚物及其作为增溶剂的用途 Download PDFInfo
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Abstract
本发明涉及包含以下组分的共聚物作为微溶于水的物质的增溶剂的用途:a)60-99重量%的N-乙烯基己内酰胺;b)1-40重量%的至少一种选自以下的单体b):b1)单烯属不饱和C3-C8羧酸的C8-C30烷基酯,b2)具有C8-C30烷基的丙烯酸或甲基丙烯酸的N-烷基-或N,N-二烷基酰胺,b3)未支化的脂族C8-C30羧酸的乙烯基酯,b4)C8-C30烷基乙烯基醚。
Description
本发明涉及基于N-乙烯基己内酰胺的共聚物及其作为微溶于水的物质的增溶剂的用途。另外,本发明涉及相应的用于治疗人、动物和植物的制剂,以及用于工业应用的制剂。
当特别制备生物活性物质的均匀制剂时,疏水性物质(即,微溶于水的物质)的增溶已经具有非常重要的实际意义。
增溶表示使不溶于或微溶于特定溶剂(特别是水)的物质在界面活性化合物(即增溶剂)的作用下成为可溶性的。这些增溶剂能将水溶性差或不溶于水的物质转化成透明的、最多乳白色的水溶液,且这些物质的化学结构在此过程中没有发生变化(参见Chemie Lexikon,第9版,第5卷,第4203页,Thieme Verlag,Stuttgart,1992)。
所制备的被增溶物的特征在于水溶性差或不溶于水的物质以胶态溶解的形式存在于形成水溶液的表面活性化合物分子缔合物中,即所谓的胶束。所得的溶液是稳定的单相体系,表现为在视觉上是透明至乳白色的,并可以在不需要输入能量的情况下制备。
增溶剂可以例如通过使化妆品制剂和食品制剂变成透明的而改进这些制剂的外观。此外,在药物制剂的情况下,生物利用率以及进而药物的效果也可以通过使用增溶剂得到提高。
用于药物和化妆品活性成分的增溶剂主要是表面活性剂,例如乙氧基化(氢化)蓖麻油、乙氧基化脱水山梨醇脂肪酸酯或乙氧基化羟基硬脂酸。但是,迄今使用的上述增溶剂具有与应用相关的许多缺点。
公知的增溶剂对于微溶性药物(例如克霉唑)仅仅具有小的增溶效果。
EP-A 876 819公开了使用至少60重量%N-乙烯基吡咯烷酮和具有长链烷基的酰胺或酯形成的共聚物。
EP-A 948 957公开了使用单烯属不饱和羧酸(例如丙烯酸)与疏水改性共聚单体形成的共聚物,共聚单体是例如具有C8-C30烷基的不饱和羧酸N-烷基-或N,N-二烷基酰胺。
对增溶剂的另一个要求是能与微溶性物质形成所谓的“固溶体”。术语“固溶体”表示这样一种状态,其中物质以分子分散形式分布在固体基质中,例如聚合物基质中。这些固溶体例如当用于微溶性活性成分的固体药物给药形式时导致活性成分的释放得到改进。对这种固溶体的重要要求是它们即使在长期储存时也是稳定的,即活性成分不应该结晶出来。
当形成固溶体时,除了增溶剂形成固溶体的基本能力之外,增溶体的吸湿性也起到重要作用。从环境空气吸收过多水的增溶剂会导致固溶体的潮解,并导致活性成分的不利结晶。过度的吸湿性也在生产给药制剂的加工期间导致问题。
现有技术中的聚合物增溶剂的缺点是它们不能形成稳定的固溶体或者吸湿性太大。此外,它们仍然在含水体系中的增溶方面需要改进。
所以,本发明的目的是提供用于药物、化妆品、食品和农业技术或其它工业应用的新型改进的增溶剂,其不具有上述缺点。
此目的通过使用包含以下组分的共聚物实现:
a)60-99重量%的N-乙烯基己内酰胺,
b)1-40重量%的至少一种选自以下的单体:
b1)单烯属不饱和C3-C8羧酸的C8-C30烷基酯,
b2)具有C8-C30烷基的丙烯酸或甲基丙烯酸N-烷基-或N,N-二烷基酰胺,
b3)未支化的脂族C8-C30羧酸的乙烯基酯,
b4)C8-C30烷基乙烯基醚,
其中各组分的重量%数据的总和是100重量%。
另外,本发明涉及用于微溶于水的物质的制剂。
如果合适的话,所述共聚物可以含有0-39重量%的至少一种其它可自由基共聚的单体c),其中各组分a)至c)的重量%数据的总和是100重量%。
单体a)在共聚物中的比例优选是70-95重量%,特别优选75-90重量%。
合适的单体b)是:单烯属不饱和C3-C8羧酸的N-C8-C30烷基-或N,N--C8-C30二烷基酰胺,其中烷基是具有8-30、优选8-18个碳原子的直链或支链的脂族或脂环族烷基。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、马来酸或所述羧酸的混合物。
优选的酰胺化单体是例如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-鲸醋基丙烯酰胺、N-鲸醋基-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。
在马来酸酐用作共聚单体的情况下,其可以按照聚合物类似方式与N-烷基胺进行开环反应,得到相应的酰胺。
其它可以使用的共聚单体b)是单烯属不饱和C3-C8羧酸与C8-C30醇、优选C8-C18醇形成的酯。
在这方面,重要的是具有8-18个碳原子链长的脂肪醇丙烯酸酯和甲基丙烯酸酯,其中烷基可以是支化或非支化的。
特别是,可以提到:丙烯酸辛酯、丙烯酸2-乙基己酯、丙烯酸壬基酯、丙烯酸癸基酯、丙烯酸月桂基酯、丙烯酸肉豆蔻基酯、丙烯酸鲸醋基酯、丙烯酸硬脂基酯、丙烯酸油基酯、丙烯酸二十二烷基酯、甲基丙烯酸辛酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸壬基酯、甲基丙烯酸癸基酯、甲基丙烯酸月桂基酯、甲基丙烯酸肉豆蔻基酯、甲基丙烯酸鲸醋基酯、甲基丙烯酸硬脂基酯、甲基丙烯酸油基酯、甲基丙烯酸二十二烷基酯、丙烯酸叔丁基环己酯。
作为其它的组分b),可以使用长链脂族的、饱和或不饱和的、非支化的C8-C30羧酸的乙烯基酯,所述羧酸是例如辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸、二十二烷酸、二十四烷酸、二十六烷酸和三十烷酸。
另外,作为单体b),C8-C30-烷基乙烯基醚、优选C8-C18-烷基乙烯基醚可以进行共聚。可以提到的优选的乙烯基醚的烷基是支化或非支化的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。
特别优选的单体b)是丙烯酸月桂基酯和月桂酸乙烯酯。
单体b)的比例优选是1-25重量%,非常特别优选5-15重量%。
合适的其它可自由基共聚的单体c)是:具有3-8个碳原子的单烯属不饱和羧酸或其盐,例如丙烯酸、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。
对于此组单体,优选使用丙烯酸、甲基丙烯酸或所述羧酸的混合物。
单烯属不饱和羧酸可以在共聚中作为游离酸、作为羧酸以及以部分或完全中和的形式使用。
对于上述羧酸的中和,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。
其它合适的共聚单体c)是例如单烯属不饱和C3-C8羧酸与C1-C4-一元醇或二元醇形成的酯,或所述酸的腈。可以提到的例子是:丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、丙烯酸羟乙酯、丙烯酸羟丙酯、丙烯酸羟丁酯、甲基丙烯酸羟乙酯、甲基丙烯酸羟丙酯、丙烯酸羟基异丁酯、甲基丙烯酸羟基异丁酯、马来酸单甲酯、马来酸二甲酯、马来酸单乙酯、马来酸二乙酯、丙烯腈、甲基丙烯腈。其它合适的共聚单体c)是丙烯酸或甲基丙烯酸的N-C1-C4烷基-或N,N-C1-C4-二烷基-酰胺,例如N-二甲基丙烯酰胺或N-叔丁基丙烯酰胺。也合适的是丙烯酸N,N-C1-C4二烷基氨基-C1-C4烷基酯,例如丙烯酸二甲基氨基乙酯、丙烯酸二乙基氨基乙酯、甲基丙烯酸二甲基氨基乙酯、甲基丙烯酸二乙基氨基乙酯,上述单体与羧酸或无机酸形成的盐,以及季化产物。
其它合适的单体c)是例如:丙烯酰氨基乙醇酸;单烯属不饱和磺酸,例如乙烯基磺酸、烯丙基磺酸、甲代烯丙基磺酸、苯乙烯磺酸,丙烯酸(3-磺丙基)酯、甲基丙烯酸(3-磺丙基)酯和丙烯酰氨基丙磺酸;含膦酸基团的单烯属不饱和单体,例如乙烯基膦酸、烯丙基膦酸、丙烯酰氨基甲烷丙烷膦酸。
另外,作为单体c),共聚物也可以含有乙酸乙烯酯、N-乙烯基吡咯烷酮、N-乙烯基咪唑、甲基化N-乙烯基咪唑或N-乙烯基甲酰胺。
当然也可以使用上述单体的混合物。
特别优选的单体c)是丙烯酸、甲基丙烯酸或衣康酸以及它们的碱金属盐,非常特别优选丙烯酸钠。
单体结构单元c)在共聚物中的比例优选是0-15重量%,特别优选2-10重量%。
按照Fikentscher在0.1摩尔NaCl溶液中在1%浓度下检测,本发明使用的共聚物的K值是5-60,优选10-35,特别优选12-30。
共聚物通过相应单体的自由基聚合制备。
制备可以通过公知的方法进行,例如溶液聚合、沉淀聚合或通过反相悬浮聚合,其中使用能在聚合条件下形成自由基的化合物。
聚合温度通常是30-200℃,优选40-110℃。合适的引发剂是例如偶氮和过氧化合物,以及常规的氧化还原引发剂体系,例如过氧化氢与还原化合物组合,还原化合物是例如亚硫酸钠、亚硫酸氢钠、甲醛合次硫酸氢钠和酰肼。
所用的反应介质是能溶解单体的任何常规溶剂。优选使用水或醇类溶剂,例如甲醇、乙醇、正丙醇或异丙醇或这些醇与水的混合物。
为了确保反应得到均匀产物,有利的是向反应溶液分别提供单体和起始剂。这可以例如以对于各反应物的单独进料形式提供。
聚合也可以在常规调节剂的存在下进行,如果需要达到较低分子量的话。
所得有机溶液的固含量通常是20-60重量%,特别是20-35重量%。
然后,可以通过水蒸气蒸馏除去用于聚合的非水性溶剂,并用水代替。
共聚物的水溶液可以通过各种干燥工艺被转化成粉末形式,例如喷雾干燥、流化喷雾干燥、转鼓干燥或冷冻干燥,可以由粉末形式通过再分散在水中再次制备水分散液或溶液。
应用:
根据本发明使用的共聚物原则上可以用于所有不溶于水或微溶于水的物质要作为含水制剂或要在含水介质中发挥作用的所有领域中。因此,共聚物用作微溶于水的物质的增溶剂,特别是用作生物活性物质的增溶剂。
根据本发明,术语“微溶于水”也包括基本不溶性的物质,表示对于物质在20℃在水中的溶液,需要至少30-100g水/每g所述物质。在基本不溶性物质的情况下,需要至少10000g水/每g所述物质。
为了本发明的目的,微溶于水的生物活性物质表示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者食物补品或营养活性成分。
另外,合适的要被增溶的微溶性物质也是染料,例如无机或有机颜料。
通过本发明,提供了两亲性化合物,其特别用作药物和化妆品制剂的增溶剂,以及用作食品制剂的增溶剂。它们具有增溶以下物质的性能:药物和化妆品领域中的微溶性活性成分,微溶性食物补品例如维生素和胡萝卜素,在作物保护组合物中的微溶性活性成分,以及兽医药物活性组分。
用于化妆品的增溶剂:
根据本发明,共聚物可以用作化妆品制剂中的增溶剂。例如,它们适合作为化妆油的增溶剂。它们对于脂肪和油具有良好的增溶能力,例如花生油、霍霍巴油、椰子油、杏仁油、橄榄油、棕榈油、蓖麻油、豆油或麦芽油,或用于精油,例如矮松油、熏衣草油、迷迭香油、云杉针油、松针油、桉树油、薄荷油、香紫苏油、香柠檬油、松精油、蜜蜂花油、刺柏油、柠檬油、茴香油、小豆蔻油;薄荷油、樟脑油等,或用于这些油的混合物。
另外,本发明的聚合物可以用作不溶于水或微溶于水的UV吸收剂的增溶剂,UV吸收剂是例如2-羟基-4-甲氧基二苯酮(UvinulM 40,BASF),2,2‘,4,4‘-四羟基二苯酮(UvinulD 50),2,2‘-二羟基-4,4‘-二甲氧基二苯酮(UvinulD49),2,4-二羟基二苯酮(Uvinul400),2-氰基-3,3-二苯基丙烯酸2′-乙基己基酯(UvinulN 539),2,4,6-三苯胺基-p-(碳-2‘-乙基己基-1‘-氧基)-1,3,5-三嗪(UvinulT 150),3-(4-甲氧基亚苄基)樟脑(Eusolex6300,Merck),N,N-二甲基-4-氨基苯甲酸2-乙基己基酯(Eusolex6007),水杨酸3,3,5-三甲基环己基酯,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。
所以,本发明还涉及含有作为增溶剂的按照上述定义组成的至少一种本发明共聚物的化妆品制剂。优选这样的制剂,其中除了增溶剂之外还含有一种或多种微溶性化妆活性成分,例如上述油或UV吸收剂。
这些制剂是基于水或水/醇的被增溶物。本发明的增溶剂相对于微溶性化妆品活性成分的比率是0.2∶1至20∶1,优选1∶1至15∶1,特别优选2∶1至12∶1。
本发明增溶剂在化妆品制剂中的含量取决于活性成分,在1-50重量%、优选3-40重量%、特别优选5-30重量%的范围内。
另外,其它助剂可以加入此配料中,例如非离子、阳离子或阴离子表面活性剂,例如烷基聚苷、脂肪醇硫酸盐、脂肪醇醚硫酸盐、链烷磺酸盐、脂肪醇乙氧基化物、脂肪醇磷酸盐、烷基甜菜碱、脱水山梨醇酯、POE脱水山梨醇酯、糖脂肪酸酯、脂肪酸聚甘油酯、脂肪酸偏甘油酯、脂肪酸羧酸盐、脂肪醇磺基琥珀酸盐、脂肪酸肌氨酸盐、脂肪酸羟乙基磺酸盐、脂肪酸酒石酸盐、柠檬酸酯、有机硅共聚物、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、烷基酚乙氧基化物、脂肪胺乙氧基化物,助溶剂,例如乙二醇、丙二醇、甘油等。
其它可以加入的组分是天然或合成化合物,例如羊毛脂衍生物、胆固醇衍生物、肉豆蔻酸异丙基酯、棕榈酸异丙基酯、电解质、染料、防腐剂、酸(例如乳酸、柠檬酸)。
这些配料例如用于洗浴添加剂制剂中,例如沐浴油、须后水、面部滋养剂、头发滋养剂、古龙香水、化妆水和防晒组合物。其它应用领域是口腔护理领域,例如在漱口水、牙膏、用于牙齿的粘合膏等中。
另外,共聚物也适用于工业应用,例如用于微溶性着色剂的制剂,用于调色剂中,用于磁性颜料的制剂中,等。
增溶方法的描述:
在用于化妆品制剂的被增溶物的制备中,本发明的共聚物可以作为100%浓度的物质使用,或优选作为水溶液使用。
通常,增溶剂溶解在水中,并与在每种情况下要使用的微溶性化妆品活性成分强烈混合。
但是,也可以将增溶剂与在每种情况下要使用的微溶性化妆品活性成分强烈混合,然后在连续搅拌下加入去离子水。
用于药物应用的增溶剂:
所述共聚物也适用作任何类型的药物制剂中的增溶剂,这些药物制剂的特征是它们可以含有一种或多种不溶于水或微溶于水的药物以及维生素和/或胡萝卜素。特别是,这些是用于口腔应用的固溶体或被增溶物。
因此,所述共聚物适用于口腔给药形式中,例如片剂、胶囊、粉末、溶液。在这里,它们使得微溶性药物具有提高的生物利用率。特别优选使用活性成分和增溶剂的固溶体。
在胃肠应用的情况下,除了被增溶物之外也可以使用乳液,例如脂肪乳液。所述共聚物也适用于此目的,从而加工微溶性药物。
上述药物制剂可以通过按照常规方法和使用公知和新型的活性成分加工所述共聚物和药物活性成分获得。
本发明的用途可以另外包括药物助剂和/或稀释剂。作为助剂特别提到的是助溶剂、稳定剂、防腐剂。
所用的药物活性成分是不溶于水或稍微溶于水的物质。根据DAB 9(德国药典),药物活性成分的溶解度如下分类:稍微溶解(可溶于30-100份的溶剂),微溶(可溶于100-1000份的溶剂),基本上不溶(可溶于超过10000份的溶剂)。活性成分可以来自任何所述的领域。
可以提到的例子是苯并二氮杂化物、抗高血压药、维生素、细胞抑制剂,特别是泰素,麻醉剂,抗精神病药,抗抑郁药,抗生素,抗真菌药,杀菌剂,化疗药,泌尿科药,血小板聚集抑制剂,磺酰胺,解痉药,激素,免疫球蛋白,血清,甲状腺治疗剂,心理学药物,抗帕金森病药和其它抗高血压药,眼科药物,神经药物制剂,钙新陈代谢调节剂,肌肉松弛剂,尼古丁,降血脂药,肝病治疗剂,抗心血管病药,抗心脏病药,免疫治疗剂,调节肽及其抑制剂,催眠药,镇静剂,妇科药,痛风药,抗血栓药物,酶制剂以及转运蛋白,酶抑制剂,催吐药,循环促进剂,利尿药,诊断剂,皮质激素,胆碱药,胆道治疗剂,抗气喘药,支气管炎药,β-受体阻断剂,钙拮抗药,ACE抑制剂,抗动脉硬化药,抗炎药,抗凝聚药,抗高血压药,抗糖尿病药,抗高渗药,抗纤维蛋白溶素,抗癫痫药,止吐药,解毒剂,减肥药,抗心律失常药,抗贫血药,抗过敏药,驱虫药,止痛药,兴奋药,醛固酮拮抗剂和减肥药。
一种可能的制备变型是将增溶剂溶解在水相中,如果合适的话进行温和的加热,然后将活性成分溶解在含水的增溶剂溶液中。增溶剂和活性成分在水相中的同时溶解也是可能的。
本发明共聚物作为增溶剂的应用也可以通过将活性成分分散在增溶剂中,如果合适的话加热,并与水在搅拌下混合进行。
另外,增溶剂也可以在熔体中与活性成分一起加工。特别是,可以以此方式获得固溶体。对此合适的特别也是熔体挤出工艺。另一种制备固溶体的方式也是制备增溶剂和活性成分在合适有机溶剂中的溶液,然后通过常规方法除去溶剂。
本发明因此还提供含有作为增溶剂的至少一种本发明共聚物的药物制剂。优选这样的制剂,其中除了增溶剂之外还含有不溶于水或微溶于水的药物活性成分,例如来自所述的上述领域。
在上述药物制剂中,特别优选作为口腔给药制剂的那些。
本发明增溶剂在药物制剂中的含量取决于活性成分,在1-75重量%的范围内,优选5-50重量%,特别优选10-30重量%。
其它特别优选的实施方案指其中活性成分和增溶剂作为固溶体存在的药物制剂。这里,增溶剂与活性成分的重量比优选是1∶1至4∶1。
用于食品制剂的增溶剂:
除了用于化妆品和药物领域之外,本发明的共聚物也适合在食品领域中用作不溶于水或微溶于水的营养品、助剂或添加剂的增溶剂,例如可溶于脂肪的维生素或胡萝卜素。可以提到的例子是用胡萝卜素着色的透明饮料。
用于作物保护制剂的增溶剂:
本发明共聚物在农业化学中作为增溶剂的应用可以特别包括含有农药、除草剂、杀菌剂或杀虫剂的配料,特别是作为喷洒组合物或倾倒混合物使用的那些作物保护组合物制剂。
本发明共聚物的特征在于具有特别优良的增溶效果。
在下面的实施例中,更详细地说明本发明共聚物的制备和应用。
实施例
为了制备聚合物,使用以下设备:
2L设备,其带有工艺控制的水浴、锚式搅拌器和温度计。该设备具有对于三种进料的连接器、回流冷凝器和用于引入氮气或水蒸气的入口管。
根据Fikentscher的K值:聚合物在0.1摩尔NaCl水溶液中的1重量%浓度溶液。
所用的缩写:
VCap:N-乙烯基己内酰胺
VP:N-乙烯基吡咯烷酮
LA:丙烯酸月桂基酯
VL:月桂酸乙烯酯
NaA:丙烯酸钠
实施例1
N-乙烯基己内酰胺/丙烯酸月桂基酯/丙烯酸钠(重量比85/5/10)共聚物的制备
初始进料用氮气吹扫,并加热到75℃的反应器内部温度。然后在150rpm的搅拌器速度下,在4小时内加入进料1和进料2,在4.5小时内加入进料3。然后将混合物在75℃再进行后聚合2小时。然后蒸馏出300ml的乙醇,并使反应混合物进行水蒸气蒸馏。为此,在102℃的内部温度,将1L的水作为水蒸气在1.5小时内引入。在蒸馏之后,用500ml水稀释聚合物溶液。
量 物质
g
初始进料 350.0 乙醇
10.0 VCap
进料1 400.0 乙醇
330.0 VCap
20.0 LA
进料2 107.2g NaA在水中的37.3重量%溶液
进料3 89.3 乙醇
10.7 过新戊酸叔丁酯*
这得到透明的粘性溶液。K值是17.1。
实施例2
N-乙烯基己内酰胺/丙烯酸月桂基酯/丙烯酸钠(重量比80/10/10)共聚物的制备
按照实施例1所述类似地进行制备。
量 物质
g
初始进料 350.0 乙醇
10.0 VCap
进料1 400.0 乙醇
310.0 VCap
40.0 LA
进料2
107.2 NaA在水中的37.3重量%溶液
42.8 水
进料3 89.3 乙醇
10.7 过新戊酸叔丁酯
这得到透明的粘性溶液。K值是14.9。
实施例3
N-乙烯基己内酰胺/N-乙烯基吡咯烷酮/月桂酸乙烯基酯(重量比60/30/10)共聚物的制备
异丙醇和部分进料1的初始进料用氮气吹扫,并在75rpm的搅拌速度下加热到75℃的反应器内部温度。在达到73℃的内部温度时,加入部分进料2,并使混合物聚合10分钟。然后在4小时内加入其余的进料1,并在5小时内加入其余的进料2。然后将混合物在75℃再进行后聚合2小时。然后蒸馏出异丙醇,用水稀释反应混合物,并进行水蒸气蒸馏,得到固含量为31.2重量%的溶液。在1重量%水溶液中检测的K值是13.5。
量 物质
g
初始进料 100.0 异丙醇
10.0 VCap
75.0 进料1
5.33 进料2
进料1 250.0 异丙醇
300.0 VCap
150.0 VP
50.0 VL
进料2 100.0 异丙醇
6.66 过新戊酸叔丁酯
这得到透明的粘性溶液。K值是14.9。
●过新戊酸叔丁酯:在脂族化合物混合物中的75重量%活性,来自Degussa的TBPPI-75-AL(82049Pullach/德国)
为了对比,制备以下共聚物:
对比例A:N-乙烯基吡咯烷酮/丙烯酸月桂基酯/丙烯酸钠(重量比80/10/10)的共聚物,K值为13.5
对比例B:N-乙烯基吡咯烷酮/丙烯酸月桂基酯/丙烯酸钠(重量比85/5/10)的共聚物,K值为14.4
制备固溶体:一般工序
为了制备聚合物/活性成分混合物,将活性成分和聚合物按照1∶1的重量比(在每种情况下2g)称量加入合适的玻璃容器中,然后加入作为溶剂的16ml二甲基甲酰胺。该混合物在20℃在磁力搅拌器的作用下搅拌24小时。然后使用120微米刮刀在玻璃片上拉出溶液。该溶液在通风橱中在室温干燥0.5小时,然后在干燥室中于50℃和10毫巴再干燥0.5小时,从而除去所有溶剂。然后目测评价样品。如果膜是透明的且在7天后没有结晶出活性成分,则认为活性成分是稳定溶解于聚合物中的(表1中的数据:50%溶解)。如果使用50重量%的活性成分含量不能获得固溶体,则使用33重量%的活性成分含量重复进行实验(表1中的数据:33%溶解)。总体上,本发明的共聚物显示出形成固溶体的更高能力。
表1:固溶体的稳定性
共聚物 | 卡马西平 | *** | 吡罗昔康 | 克霉唑 |
实施例1 | 50%溶解 | 50%溶解 | 33%溶解 | 50%溶解 |
实施例2 | 33%溶解 | 50%溶解 | 50%溶解 | 50%溶解 |
实施例3 | 50%溶解 | 50%溶解 | 33%溶解 | 50%溶解 |
对比例A | 33%溶解 | 33%溶解 | 33%溶解 | 33%溶解 |
对比例B | 33%溶解 | 33%溶解 | 33%溶解 | 33%溶解 |
增溶物的制备
将2g共聚物称量加入烧杯中。然后,在每种情况下将一种下述药物称量加入混合物中以获得超饱和的溶液。(如果称量加入的物质溶解在介质中,则初始重量增加直到形成沉淀)。
活性成分的添加量:17-β-***0.2g;吡罗昔康0.2g;克霉唑0.2g;卡马西平0.3g。
然后加入磷酸盐缓冲剂pH7.0,直到增溶剂和磷酸盐缓冲剂以1∶10的重量比存在。使用磁力搅拌器,将该混合物在20℃搅拌72小时。然后静置至少1小时。在过滤混合物之后,用光度计检测,并确定活性成分的含量。
特别在生理学上有意义的37℃增溶的情况下,本发明的增溶剂是显著更优异的。
表2:20℃的增溶,g/100ml
共聚物 | 卡马西平 | *** | 吡罗昔康 |
实施例1 | 0.14 | 0.24 | 0.49 |
实施例2 | 0.21 | 0.44 | 0.47 |
对比例A | 0.11 | 0.12 | 0.28 |
表3:37℃的增溶,g/100ml
共聚物 | 卡马西平 | *** | 吡罗昔康 | 克霉唑 |
实施例1 | 0.26 | 0.22 | 0.75 | - |
实施例2 | 0.37 | 0.36 | 0.59 | 0,12 |
对比例A | 0.16 | 0.12 | 0.31 | - |
测定吸湿性
为了检测吸湿性,在恒定大气湿度(76%)下储存24小时之后检测共聚物样品的重量增加,并在14天之后再次核查。在14天后,这些值没有变化。本发明的共聚物显示显著更低的吸湿性。
表4
Claims (27)
1.包含以下组分的共聚物作为微溶于水的物质的增溶剂的用途:
a)60-99重量%的N-乙烯基己内酰胺,
b)1-40重量%的至少一种选自以下的单体b):
b1)单烯属不饱和C3-C8羧酸的C8-C30烷基酯,
b2)具有C8-C30烷基的丙烯酸或甲基丙烯酸N-烷基-或N,N-二烷基酰胺,
b3)未支化的脂族C8-C30羧酸的乙烯基酯,
b4)C8-C30烷基乙烯基醚。
2.权利要求1的用途,其中共聚物含有0-39重量%的至少一种其它可自由基共聚的单体c),所述单体c)选自:具有3-8个碳原子的单烯属不饱和羧酸及其盐,单烯属不饱和C3-C8羧酸与C1-C4-一元醇或二元醇形成的酯以及所述酸的腈,丙烯酸或甲基丙烯酸的N-C1-C4烷基-或N,N-C1-C4二烷基-酰胺,丙烯酸N,N-CX-C4二烷基氨基-C1-C4烷基酯及其盐,丙烯酰氨基乙醇酸,单烯属不饱和磺酸,含膦酸基团的单烯属不饱和单体,乙酸乙烯酯、N-乙烯基吡咯烷酮,N-乙烯基咪唑,以及N-乙烯基甲酰胺,其中各组分a)至c)的重量%数据的总和是100重量%。
3.权利要求1或2的用途,其中共聚物含有:
a)70-95重量%的N-乙烯基己内酰胺,
b)5-30重量%的至少一种单体b),
c)0-25重量%的至少一种其它可自由基共聚的单体c)。
4.权利要求1-3中任一项的用途,其中共聚物含有2-10重量%的单体c)。
5.权利要求1-4中任一项的用途,其中共聚物含有丙烯酸或甲基丙烯酸的C8-C30烷基酯作为单体b)。
6.权利要求1-5中任一项的用途,其中共聚物含有丙烯酸月桂基酯作为单体b)。
7.权利要求1-6中任一项的用途,其中共聚物含有月桂酸乙烯基酯作为单体b)。
8.权利要求1-7中任一项的用途,其中共聚物含有丙烯酸钠作为单体c)。
9.权利要求1-8中任一项的用途,其中共聚物具有12-30的K值。
10.权利要求1-9中任一项的用途,其中共聚物是通过单体a)至c)的自由基聚合反应获得的。
11.权利要求1-10中任一项的用途,其中微溶于水的物质是生物活性物质。
12.权利要求1-11中任一项的用途,用于制备治疗疾病的药物制剂。
13.权利要求1-11中任一项的用途,用于化妆品制剂。
14.权利要求1-11中任一项的用途,用于农业化学制剂。
15.权利要求1-11中任一项的用途,用于食品补充剂或营养剂。
16.权利要求1-11中任一项的用途,用于食品。
17.权利要求1-11中任一项的用途,用于染料制剂。
18.一种微溶于水的物质的制剂,其含有作为增溶剂的共聚物,所述共聚物含有:
a)60-99重量%的N-乙烯基己内酰胺,
b)1-40重量%的至少一种选自以下的单体b):
b1)单烯属不饱和C3-C8羧酸的C8-C30烷基酯,
b2)具有C8-C30烷基的丙烯酸或甲基丙烯酸的N-烷基-或N,N-二烷基酰胺,
b3)未支化的脂族C8-C30羧酸的乙烯基酯,
b4)C8-C30烷基乙烯基醚,
19.权利要求18的制剂,其中共聚物含有0-39重量%的至少一种其它可自由基共聚的单体c),并且各组分a)至c)的重量%数据的总和是100重量%。
20.权利要求18或19的制剂,其中微溶于水的物质以固溶体的形式存在于共聚物中。
21.权利要求18-20中任一项的制剂,其含有生物活性物质作为微溶于水的物质。
22.权利要求18-21中任一项的制剂,其含有药物活性成分作为微溶于水的生物活性物质。
23.权利要求22的制剂,其是口服给药形式。
24.权利要求18-21中任一项的制剂,其含有化妆品活性成分作为微溶于水的生物活性物质。
25.权利要求18-21中任一项的制剂,其含有农业化学活性成分作为微溶于水的生物活性物质。
26.权利要求18-21中任一项的制剂,其含有食品补充剂或营养活性成分作为微溶于水的生物活性物质。
27.权利要求18或20的制剂,其含有染料作为微溶于水的物质。
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EP (1) | EP1915407A2 (zh) |
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Cited By (2)
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CN107920998A (zh) * | 2015-08-21 | 2018-04-17 | 巴斯夫欧洲公司 | 基于n‑乙烯基吡咯烷酮和丙烯酸的水溶性聚合物作为药物助剂的用途 |
CN108623744A (zh) * | 2018-06-01 | 2018-10-09 | 辽宁奥克医药辅料股份有限公司 | 共聚物、增溶剂及制备方法 |
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DE10026698A1 (de) | 2000-05-30 | 2001-12-06 | Basf Ag | Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung |
US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
CN103190396A (zh) * | 2008-02-21 | 2013-07-10 | 巴斯夫欧洲公司 | 涂覆的惰性颗粒 |
BR112013020877B1 (pt) | 2011-02-28 | 2020-06-02 | Basf Se | Processo para produzir composições de revestimento pulverulentas |
US20130236505A1 (en) | 2012-03-09 | 2013-09-12 | Basf Se | Production Of Pharmaceutical Protective Coatings With Good Resistance In A Neutral Environment |
EP2636403A1 (de) | 2012-03-09 | 2013-09-11 | Basf Se | Herstellung von pharmazeutischen protektiven Überzügen mit guter Resistenz im neutralen Milieu |
EP3728353B1 (en) * | 2017-12-20 | 2023-08-02 | Basf Se | Novel terpolymers and their use in pharmaceutical dosage forms |
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US5191043A (en) * | 1992-03-16 | 1993-03-02 | Isp Investments Inc. | Precipitation polmerization of copolymers of a vinyl lactam and a polymerizable carboxylic acid having a molecular weight of less than 20,000 in a cosolvent mixture of an aliphatic hydrocarbon solvent and isopropanol |
JPH09241335A (ja) * | 1996-03-08 | 1997-09-16 | Nippon Shokubai Co Ltd | 難燃材 |
JP3869898B2 (ja) * | 1997-01-10 | 2007-01-17 | 住友精化株式会社 | アクリルアミド系重合体分散液の製造方法 |
DE19719187A1 (de) * | 1997-05-07 | 1998-11-12 | Basf Ag | Verwendung von Copolymerisaten des N-Vinyl-pyrrolidons in Zubereitungen wasserunlöslicher Stoffe |
US6177068B1 (en) * | 1997-12-10 | 2001-01-23 | Isp Investments Inc. | Vinyl amide polymer delivery system for hair and skin treating compositions |
DE19811919A1 (de) * | 1998-03-18 | 1999-09-23 | Basf Ag | Verwendung von Copolymerisaten monoethylenisch ungesättigter Carbonsäuren als Solubilisatoren |
US7019046B2 (en) * | 2001-08-08 | 2006-03-28 | Isp Investments Inc. | Aqueous suspension agent for water insoluble compounds |
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2006
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- 2006-08-02 US US12/063,492 patent/US20100137455A1/en not_active Abandoned
- 2006-08-02 CN CNA2006800375519A patent/CN101283008A/zh active Pending
- 2006-08-02 JP JP2008525552A patent/JP2009504605A/ja not_active Withdrawn
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CN107920998A (zh) * | 2015-08-21 | 2018-04-17 | 巴斯夫欧洲公司 | 基于n‑乙烯基吡咯烷酮和丙烯酸的水溶性聚合物作为药物助剂的用途 |
CN108623744A (zh) * | 2018-06-01 | 2018-10-09 | 辽宁奥克医药辅料股份有限公司 | 共聚物、增溶剂及制备方法 |
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WO2007017452A2 (de) | 2007-02-15 |
EP1915407A2 (de) | 2008-04-30 |
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