CN101460149A - 醋酸乙烯酯-磺酸盐共聚物作为微水溶性化合物的加溶剂的用途 - Google Patents
醋酸乙烯酯-磺酸盐共聚物作为微水溶性化合物的加溶剂的用途 Download PDFInfo
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- CN101460149A CN101460149A CNA2007800210440A CN200780021044A CN101460149A CN 101460149 A CN101460149 A CN 101460149A CN A2007800210440 A CNA2007800210440 A CN A2007800210440A CN 200780021044 A CN200780021044 A CN 200780021044A CN 101460149 A CN101460149 A CN 101460149A
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- slightly water
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Abstract
共聚物作为微水溶性物质的加溶剂的用途,其中所述共聚物通过如下单体的自由基引发共聚获得:a)80-99.5重量%醋酸乙烯酯和b)0.5-20重量%含磺酸盐基团的单烯键不饱和单体。
Description
本发明涉及醋酸乙烯酯-磺酸盐共聚物作为微水溶性生物活性物质的加溶剂的用途。本发明进一步涉及用于人、动物和植物的相应制剂,并涉及具体共聚物。
在生物活性物质的均相制剂生产中,疏水的,即微水溶性物质的加溶已具有非常显著的实践重要性。
加溶指通过表面活性化合物,即加溶剂使微溶于或不溶于特定溶剂,尤其是水的物质可溶。这样的加溶剂可将水溶性差或水不溶性物质转变为澄清,最多为乳色的水溶液,而不会因此改变这些物质的化学结构(参见 Chemie Lexikon,第9版,第5卷,第4203页,Thieme Verlag,Stuttgart,1992)。
制备的加溶物的特征为:水溶性差或水不溶性物质以胶体溶液的形式存在于水溶液中形成的表面活性化合物分子聚集体-例如,所谓的胶束中。所得溶液为外观光学透明或乳色的稳定单相体系,且无需能量输入就可制备。
通过使配制剂变透明,加溶剂例如可改善化妆品配制剂和流体制剂的外观。在药物制剂情形中,通过使用加溶剂可另外提高生物利用率并因此提高药效。
用于药物和化妆品活性物质的加溶剂主要为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。但是,上述和迄今所用的加溶剂在使用时显露出很多技术缺点。
用于一些微溶药物如克霉唑的已知加溶剂的加溶效果仍然很低。
此外,迄今公开的加溶剂通常为液态或半固态化合物,其因此而表现出不太有利的加工性能。
醋酸乙烯酯-磺酸盐共聚物本身已知。例如,在US 2,834,759中描述了相应的共聚物及其用作纺织品整理剂的用途。
JP-A 51003383公开了醋酸乙烯酯和烯丙基磺酸盐共聚物及其作为环氧树脂乳化剂的用途。
JP-A 50160334公开了醋酸乙烯酯和烯丙基磺酸盐共聚物及其作为丙烯酸树脂涂料组合物乳化剂的用途。
JP-A 09202812公开了在少量烯丙基磺酸盐存在下制备聚乙烯基酯的方法,已知该烯丙基磺酸盐作为相转移剂。
GB 1350282公开了醋酸乙烯酯和少量不饱和磺酸盐的共聚物作为涂布剂的用途。
本发明目的是提供用于药物、化妆品、食品工业和农业技术应用的新型加溶剂,它们可在水性介质中作为合适微水溶性活性成分的加溶剂。
根据本发明,通过使用醋酸乙烯酯-磺酸盐共聚物作为微水溶性物质的加溶剂来达到这一目的。
根据本发明,醋酸乙烯酯-磺酸盐共聚物定义为醋酸乙烯酯和包含磺酸盐基团的单烯键不饱和单体以及,如果合适,其它的共聚单体的共聚物。
适用于本发明的包含磺酸盐基团的单体为单烯键不饱和磺酸化合物。合适的磺酸化合物例如为丙烯酸或甲基丙烯酸的磺基烷基酯,如丙烯酸磺基丙基酯或甲基丙烯酸磺基丙基酯。类似合适的为丙烯酸或甲基丙烯酸的线性或支化C1-C10烷基磺酰胺,例如丙烯酰胺基甲基丙烷磺酸(AMPS)。合适的还有包含2-10个C原子的ω-烯烃-1-磺酸。
优选单体选自乙烯基磺酸盐、烯丙基磺酸盐、甲基烯丙基磺酸盐(2-甲基-2-丙烯磺酸盐)、丙烯酸磺基丙基酯和甲基丙烯酸磺基丙基酯。
磺酸盐单体一般以其盐的形式使用。尤其合适的盐为碱金属盐,如锂、钾或钠盐,优选钠盐和钾盐。磺酸盐单体一般以水溶液形式加入聚合,磺酸盐单体的浓度可能为20-70重量%,优选20-40重量%。
在另一实施方案中,含磺酸单体也可以固体使用并溶解或悬浮在溶剂中。聚合期间单体缓慢溶解。
含磺酸盐基团的共聚物可通过a)80-99.5重量%醋酸乙烯酯和b)0.5-20重量%磺酸盐单体的共聚得到。优选采用a)85-98重量%和b)2-15重量%,尤其优选a)85-95重量%和b)5-15重量%。
制备醋酸乙烯酯-磺酸盐共聚物的一般方法本身已知。采用水混溶性有机溶剂以自由基引发聚合进行制备。合适溶剂的实例为醇类如甲醇、乙醇、正丙醇和异丙醇,以及二醇类如乙二醇和丙三醇。合适的溶剂还有乙酸酯,例如乙酸乙酯或乙酸丁酯。优选溶剂为正丙醇。
优选聚合在60-100℃温度下进行。聚合可以在大气压下进行或在至多1.5兆帕的超计大气压下进行,优选大气压。
聚合通过使用自由基引发剂引发。以所用单体计,引发剂或引发剂混合物的用量为0.01-10重量%,优选为0.3-5重量%。
在本发明的优选实施方案中,聚合进行方式是首先使用油溶性自由基引发剂,根据本发明,其表示可溶于有机溶剂而不溶于水的自由基引发剂,并在后聚合开始时使用水溶性自由基引发剂。在进料方法中,后聚合阶段开始于所有单体都已完全加入后。在分批方法中,通常认为后聚合阶段开始于总反应时间的三分之二以后。
合适的自由基引发剂为有机和无机过氧化物,如过硫酸钠或偶氮引发剂如2,2′-偶氮二[2-(2-咪唑啉-2-基)丙烷]二盐酸盐、2,2′-偶氮二(2-甲基丙酰胺)二盐酸盐)、2,2′-偶氮二(2-脒基丙烷)二盐酸盐、2,2′-偶氮二(2-甲基丁腈)、2,2′-偶氮二[2-(2-咪唑啉-2-基)丙烷]、2,2′-偶氮二(2-甲基丁腈)、2,2′-偶氮二异丁腈、2,2′-偶氮二(2,4-二甲基戊腈)、2,2′-偶氮二(2-甲基丙酸)二甲基酯、2,2′-偶氮二(4-甲氧基-2,4-二甲基戊腈)。
过氧化物引发剂的实例为过氧化二苯甲酰、过氧二乙酰、过氧化琥珀酰、过新戊酸叔丁酯、2-乙基己酸叔丁酯、过新癸酸叔丁酯、过马来酸叔丁酯、二(叔丁基过氧)环己烷、碳酸叔丁基过氧异丙基酯、过乙酸叔丁酯、2,2-二(叔丁基过氧)丁烷、过氧化二枯基、过氧化二叔戊基、过氧化二叔丁基、萜烷过氧化氢、氢过氧化蒎烷、氢过氧化枯烯、过氧化氢叔丁基、过氧化氢及上述引发剂的混合物。所述引发剂还可与氧化还原组分如抗坏血酸组合使用。
聚合期间尤其优选使用可溶于溶剂(因此水溶性差)的自由基引发剂。优选可溶于溶剂的自由基引发剂的实例为2,2′-偶氮二异丁腈、2,2′-偶氮二(2-甲基丁腈)、2,2′-偶氮二(2,4-二甲基戊腈)、2,2′-偶氮二(2-甲基丙酸)二甲基酯、2,2′-偶氮二(4-甲氧基-2,4-二甲基戊腈)、过氧化二苯甲酰、过氧二乙酰、过氧化琥珀酰、过新戊酸叔丁酯、2-乙基己酸叔丁酯、过新癸酸叔丁酯、过马来酸叔丁酯、二(叔丁基过氧)环己烷、碳酸叔丁基过氧异丙基酯、过乙酸叔丁酯、2,2-二(叔丁基过氧)丁烷、过氧化二枯基、过氧化二叔戊基、过氧化二叔丁基、萜烷过氧化氢、氢过氧化蒎烷、氢过氧化枯烯。
自由基聚合如果合适可在乳化剂、如果合适其他保护性胶体、如果合适缓冲体系的存在下进行,并且如果合适随后用碱或酸进行pH值调节。
合适的分子量调节剂为巯基化合物如烷基硫醇,例如正十二烷基硫醇、叔十二烷基硫醇、巯基乙酸及它们的酯,巯基链烷醇如巯基乙醇。更多合适的调节剂见例如DE 197 12 247 A1,第4页。以待聚合单体的量计,分子量调节剂的必需量为0-5重量%,尤其是0.05-2重量%,尤其优选0.1-1.5重量%。优选使用巯基乙醇。
根据本发明可使用的共聚物还可在合适双官能交联剂组分(交联剂)存在时和/或在合适调节剂存在时制备。
合适的交联剂为具有交联功能的单体,例如分子中含有至少两个烯键不饱和的非共轭双键的化合物。
它们的实例为丙烯酸酯、甲基丙烯酸酯、至少二元醇的烯丙基醚或乙烯基醚。潜在醇的OH基团可进一步完全或部分醚化或酯化;但是,交联剂包含至少两个烯键不饱和基团。
潜在醇的实例为二元醇如1,2-乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丁-2-烯-1,4-二醇、1,2-戊二醇、1,5-戊二醇、1,2-己二醇、1,6-己二醇、1,10-癸二醇、1,2-十二烷二醇、1,12-十二烷二醇、新戊二醇、3-甲基戊烷-1,5-二醇、2,5-二甲基-1,3-己二醇、2,2,4-三甲基-1,3-戊二醇、1,2-环己烷二醇、1,4-环己烷二醇、1,4-二(羟甲基)环己烷、羟基新戊酸新戊二醇单酯、2,2-二(4-羟苯基)丙烷、2,2-二[4-(2-羟丙基)苯基]丙烷、二甘醇、三甘醇、四甘醇、双丙甘醇、三丙二醇、四丙二醇、3-硫代戊烷-1,5-二醇以及各自分子量为200-10000的聚乙二醇、聚丙二醇和聚四氢呋喃。除了环氧乙烷和环氧丙烷的均聚物外,还可能使用环氧乙烷或环氧丙烷的嵌段共聚物或包含引入的环氧乙烷和环氧丙烷基团的共聚物。含超过两个OH基团的潜在醇的实例为三羟甲基丙烷、丙三醇、季戊四醇、1,2,5-戊三醇、1,2,6-己三醇、三乙氧基三聚氰酸、失水山梨糖醇,糖类如蔗糖、葡萄糖、甘露糖。当然,多元醇也可在与环氧乙烷或环氧丙烷反应后作为相应的乙氧基化物或丙氧基化物使用。多元醇也可首先通过与表氯醇反应转化为相应的缩水甘油醚。
其它合适的交联剂为乙烯基酯或一元不饱和醇与烯键不饱和C3-C6羧酸的酯,该羧酸例如丙烯酸、甲基丙烯酸、衣康酸、顺丁烯二酸或反丁烯二酸。这样醇的实例为烯丙醇、1-丁烯-3-醇、5-己烯-1-醇、1-辛烯-3-醇、9-癸烯-1-醇、二环戊烯醇、10-十一碳烯-1-醇、肉桂醇、香茅醇、巴豆醇或顺-g-十八碳烯-1-醇。但是,一元不饱和醇也可用多元羧酸,例如丙二酸、酒石酸、偏苯三酸、邻苯二甲酸、对苯二甲酸、柠檬酸或琥珀酸酯化。
其它合适的交联剂为不饱和羧酸与上述多元醇的酯,例如油酸、肉桂酸、巴豆酸或10-十一碳烯酸。
另外合适的交联剂为含有至少两个双键的直链或支链、线性或环状、脂族或芳族烃,其中对于脂族烃的情况,双键必须不共轭,例如二乙烯基苯、二乙烯基甲苯、1,7-辛二烯、1,9-癸二烯、4-乙烯基-1-环己烯、三乙烯基环己烷或分子量为200-20000的聚丁二烯。
其它合适的交联剂为丙烯酰胺、甲基丙烯酰胺和至少双官能胺的N-烯丙基胺。这类胺的实例为1,2-二氨基甲烷、1,2-二氨基乙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、1,12-十二烷基二胺、哌嗪、二亚乙基三胺或异佛尔酮二胺。类似合适的为来自烯丙胺和不饱和羧酸如丙烯酸、甲基丙烯酸、衣康酸、顺丁烯二酸或前述至少二元羧酸的酰胺。
其它合适的交联剂为三烯丙基胺和三烯丙基单烷基铵盐,如三烯丙基甲基氯化铵或-甲基硫酸铵。
还合适的交联剂为脲衍生物的N-乙烯基化合物、至少二官能酰胺、氰尿酸酯或氨基甲酸酯,例如脲、亚乙基脲、亚丙基脲或酒石酰胺,如N,N′-二乙烯基亚乙基脲或N,N′-二乙烯基亚丙基脲。
其它合适的交联剂为二乙烯基二噁烷、四烯丙基硅烷或四乙烯基硅烷。
当然,还可使用上述化合物的混合物。优选使用可溶于单体混合物的那些交联剂。
单体或单体混合物或单体的乳液与通常存在于溶液中的引发剂在聚合温度下一起加入到搅拌反应器中(分批方法),或者如果合适连续地或在多个连续阶段中计量加入到聚合反应器中(进料方法)。在进料方法中,除了有机溶剂或水(以便能对反应器进行搅拌)外,通常在实际聚合开始前还已向反应器加入部分量,少有的是聚合所用全部量的原料如乳化剂、保护胶体、单体、调节剂等或部分量的进料(通常为单体或乳液进料以及引发剂进料)。
采用这种方法得到的共聚物是水溶性或水分散性的。该共聚物以在水中为1重量%的溶液测得的Fikentscher K值为4-30,优选为5-25,尤其优选为5-15。
应用:
原则上,本发明所要用的共聚物可用于其中在水中溶解度低或为零的物质要用于水性制剂或要在水性介质中显示其效果的所有领域。因此将该共聚物用作微水溶性物质,尤其是生物活性物质的加溶剂。
根据本发明,“微水溶性”一词还包括几乎不溶的物质并指要使物质溶于20℃的水,每克该物质需要至少30-100克水。对于几乎不溶的物质,每克物质需要至少10000克水。
本发明上下文中,微水溶性生物活性物质指人或动物用活性药物成分、化妆品或农业化学活性物质或饮食补充剂或饮食活性物质。
其它适合加溶的微溶性物质还有着色剂如无机或有机颜料。
本发明特别提供两亲化合物用作药物和化妆品制剂以及食品制剂的加溶剂。它们不仅在药物和化妆品领域具有加溶微溶性活性成分、微溶性饮食补充剂如维生素和类胡罗卜素的性质,而且加溶作物保护剂中所用的微溶性活性物质和兽药活性成分。
化妆品用加溶剂:
根据本发明可以在化妆品配制剂中使用共聚物作为加溶剂。例如,它们适合作为化妆油加溶剂。它们对于脂肪和油如花生油、霍霍巴油、椰子油、杏仁油、橄榄油、棕榈油、蓖麻油、豆油或小麦胚芽油或对于香精油如矮松油、熏衣草油、迷迭香油、云杉针叶油、松针油、桉树油、薄荷油、鼠尾草油、香柠檬油、松节油、蜂花油、刺柏油、柠檬油、茴香油、豆蔻油、樟脑油等或这些油的混合物具有良好的加溶能力。
本发明的聚合物可进一步用作微水溶性或水不溶性紫外线吸收剂的加溶剂,例如2-羟基-4-甲氧基二苯甲酮( M40,来自BASF)、2,2’,4,4’-四羟基二苯甲酮( D50)、2,2’-二羟基-4,4’-二甲氧基二苯甲酮 D49)、2,4-二羟基二苯甲酮( 400)、2-氰基-3,3-二苯基丙烯酸2′-乙基己基酯( N539)、2,4,6-三苯胺基-对-(2’-乙基己基-1’-氧羰基)-1,3,5-三嗪( T150)、3-(4-甲氧基苯亚甲基)樟脑( 6300,来自Merck)、N,N-二甲基-4-氨基苯甲酸2-乙基己酯( 6007)、水杨酸3,3,5-三甲基环己酯、4-异丙基二苯甲酰甲烷( 8020)、对甲氧基肉桂酸2-乙基己酯和对甲氧基肉桂酸2-异戊酯,以及它们的混合物。
因此,本发明还涉及包含至少一种具有开始所述组成的本发明共聚物作为加溶剂的化妆品制剂。优选的制剂为除了加溶剂外,还包含一种或多种微溶性化妆品活性物质,例如上述油或紫外线吸收剂的那些。
这些配制剂为水基或水/醇基加溶物。本发明的加溶剂相对微溶性化妆品活性物质的使用比例为0.2:1-20:1、优选1:1-15:1、尤其优选2:1-12:1。
根据活性物质的不同,化妆品制剂中本发明加溶剂的含量为1-50重量%,优选3-40重量%,尤其优选5-30重量%。
还可能另外将其它辅料加入到该配制剂中,例如非离子型、阳离子型或阴离子型表面活性剂如烷基聚糖苷、脂肪醇硫酸酯、脂肪醇醚硫酸酯、链烷磺酸酯、脂肪醇乙氧基化物、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、糖类脂肪酸酯、脂肪酸聚丙三醇酯、脂肪酸偏甘油酯、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、聚硅氧烷共聚物、脂肪酸聚乙二醇酯、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、脂肪氨基乙氧基化物,共溶剂如乙二醇、丙二醇、丙三醇和其它物质。
还可加入的其它成分为天然或合成化合物,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、着色剂、防腐剂、酸(如乳酸、柠檬酸)。
将这些配制剂用于诸如沐浴添加剂如浴油、须后水、面部滋养剂、生发油、古龙水、淡香水和防晒组合物中。其它的应用领域为口腔护理领域,例如用于漱口水、牙膏、假牙粘合剂膏等。
该共聚物还适合于工业应用,如用于微溶性着色剂制剂、调色剂、磁性颜料制剂等。
加溶方法说明:
本发明的共聚物可用于制备化妆品配制剂的加溶物,或作为100%的纯物质或优选作为水溶液。
通常将加溶剂溶于水并与在各情况下使用的微溶性化妆品活性物质强力混合。
但是,加溶剂也可以先与在各情况下使用的微溶性化妆品活性物质强力混合,然后在持续搅拌的同时加入软化水。
药物应用加溶剂:
类似地,要求保护的共聚物适合作为加溶剂用于可含有一种或多种微水溶性或水不溶性药物以及维生素和/或类胡罗卜素的任何种类的药物制剂。在此,口服的水溶液或加溶物尤其重要。因此,要求保护的共聚物适用于如片剂、胶囊、粉末、溶液形式的口服剂型。这些剂型中,它们可提高微溶性药物的生物利用率。尤其是使用活性成分和加溶剂的固溶体。
除加溶剂外还可将乳液,例如脂肪乳液用于肠胃外给药。要求保护的共聚物还适用于加工用于此目的的微溶性药物。
采用常规方法并使用已知和新型的活性成分,加工要求保护的共聚物与活性药物成分可以获得上述类型的药物配制剂。
本发明的应用可另外包括药物赋形剂和/或稀释剂。特别提到的赋形剂有共溶剂、稳定剂、防腐剂。
所用活性药物成分不溶于水或难溶于水。根据DAB 9(德国药典),活性药物成分的溶解度分为以下类别:难溶(可溶于30-100份溶剂),微溶(可溶于100-1000份溶剂);几乎不溶(可溶于10000份以上溶剂)。就此而言,活性成分可来自任何适应症范围。
在此可以提到的实例为苯并二氮杂、抗高血压药、维生素、细胞抑制剂-尤其是紫杉醇(Taxol)、麻醉剂、抗精神病药、抗抑郁剂、抗生素、抗真菌药、杀真菌剂、化疗药物、泌尿药物、血小板凝聚抑制剂、磺酰胺类药物、解痉药、激素、免疫球蛋白、血清、甲状腺治疗药物、心理药物、抗帕金森药和其它的抗运动机能亢奋药、眼科药、神经病治疗产品、钙代谢调整剂、肌松剂、麻醉剂、降脂剂、肝病药物、冠脉药剂、强心剂、免疫药物、调节肽及其抑制剂、安眠药、镇静剂、妇科药物、痛风治疗药物、溶解纤维蛋白药物、酶产品和转运蛋白、酶抑制剂、催吐剂、血流刺激剂、利尿剂、诊断辅助药剂、皮质激素、胆碱能药、胆治疗药物、止喘药、支气管扩张药、β-受体阻滞剂、钙拮抗剂、ACE抑制剂、动脉硬化治疗药物、抗炎药、抗凝血剂、抗高血压药、抗低血糖药、抗高血压药、抗纤维蛋白溶解药、抗癫痫药、止吐药、解毒剂、抗糖尿病药、抗心律不齐药、补血药、抗过敏药、驱肠虫剂、镇痛剂、兴奋剂、醛固酮拮抗剂、减肥剂。
一种可能的生产变型是将加溶剂溶于水相,如果合适轻微加热,随后将活性成分溶于加溶剂水溶液。同样可以将加溶剂和活性成分同时溶于水相。
可以使用本发明的共聚物作为加溶剂,例如通过将活性成分分散于加溶剂中,如果合适进行加热,并且在搅拌的同时与水混合。
另一可能性是在熔体中加工加溶剂与活性成分。用此方法尤其有可能获得固溶体。为达此目的,熔融挤出方法也是合适的。生产固溶体的另一可能性是在合适的有机溶剂中制备加溶剂和活性成分的溶液,随后采用常用方法脱除溶剂。注塑工艺和熔融造粒工艺也适合生产固溶体。
因此,本发明总体上还涉及包含至少一种本发明共聚物作为加溶剂的药物制剂。优选的制剂为除了加溶剂外还包含微水溶性或水不溶性活性药物成分,例如来自上述适应症领域的成分的那些。
从以上提及的那些中,尤其优选的药物制剂为可以口服的配制剂。
根据活性成分,药物制剂中本发明加溶剂的含量为1-75重量%,优选为5-60重量%,尤其优选为5-50重量%。
进一步特别优选的实施方案涉及其中活性成分和加溶剂以固溶体形式存在的药物制剂。在此情况下,加溶剂与活性成分的重量比优选为1:1-4:1。食品制剂的加溶剂:
除了用于化妆品和药物外,本发明的共聚物还适合作为微水溶性或水不溶性的食品行业营养物质、辅助物质或添加剂,例如脂溶性维生素或类胡罗卜素的加溶剂。可以提及的实例为用类胡罗卜素着色的饮料。作物保护制剂的加溶剂:
在农业化学中,本发明的共聚物作为加溶剂使用尤其可包含含有杀虫剂、除草剂、杀真菌剂或杀昆虫剂的配制剂,尤其包含作为喷洒或灌溉用配制剂使用的作物保护剂的制剂。
本发明的磺酸盐共聚物以具有特别优良的加溶效果著称。
以下实施例详细说明了本发明共聚物的制备和用途。
实施例1
VAc/磺酸盐90:10
初始加料:120克甲醇,360克醋酸乙烯酯
进料1:156.9克乙烯基磺酸钠(25重量%水溶液)
进料2:1.2克过新癸酸叔丁酯,50克甲醇
在氮气气氛下于2升搅拌容器中进行制备。将初始加料在100转/分钟搅拌速度下加热到65℃。然后在2小时内加入进料1并且在3小时内加入进料2。然后继续聚合2小时。此后通过蒸汽蒸馏脱除有机溶剂,并且获得固体含量为25.4重量%的不透明水溶液。聚合物的K值为25.5(1重量%水溶液)。
实施例2
VAc/磺酸盐90:10
初始加料:153.6克甲醇,360克醋酸乙烯酯,160克烯丙基磺酸钠(25重量%水溶液),1.37克2,2′-偶氮二异丁腈。
在氮气气氛下于2升搅拌容器中进行制备。将初始加料在100转/分钟搅拌速度下加热到65℃。然后在65℃进行聚合8小时,随后通过蒸汽蒸馏脱除有机溶剂,调节水溶液使其固体含量为32重量%。聚合物的K值为5.9(1重量%水溶液)。
实施例3
VAc/磺酸盐80:20
初始加料:150克甲醇,160克醋酸乙烯酯,160克烯丙基磺酸钠(25重量%水溶液),0.69克2,2′-偶氮二异丁腈。
类似实施例2进行制备。蒸汽蒸馏后,通过冷冻干燥分离出聚合物。K值为7.6(1重量%水溶液)。
实施例4
VAc/磺酸盐90:10
初始加料:300克甲醇,180克醋酸乙烯酯
进料1:250克甲醇,20克甲基丙烯酸磺基丙基酯钾(25重量%水溶液)
进料2:1.5克过新癸酸叔丁酯,50克甲醇
进料3:1.5克过新癸酸叔丁酯
在氮气气氛下于2升搅拌容器中进行制备。将初始加料在100转/分钟搅拌速度下加热到64℃。然后在4小时内加入进料1,在5小时内加入进料2。随后加入进料3,在64℃继续聚合2小时。然后通过蒸汽蒸馏脱除有机溶剂,并且获得固体含量为27.8重量%的不透明白色水溶液。
实施例5
初始加料:120克1-丙醇
进料1: 114.3克烯丙基磺酸钠(水中35重量%)
3.40克硫酸
进料2: 1.20克2,2′-偶氮二(异丁酸甲基酯)
50克1-丙醇
进料3: 360克醋酸乙烯酯
进料4: 4.00克2,2′-偶氮二(2-脒基丙烷)二盐酸盐
50克水
在氮气气氛下于2升搅拌容器中进行制备。将初始加料在100转/分钟搅拌速度下加热到内部温度为72℃。然后在3小时内加入进料1和进料3,在4小时内加入进料2。随后在72℃持续进行1小时的聚合。然后加入进料4并在72℃继续聚合另外2小时。随后,通过蒸汽蒸馏脱除有机溶剂,并且获得固体含量为26重量%的不透明白色水溶液。聚合物的K值为9.4(1重量%水溶液)。
实施例6
类似实施例5制备实施例6,不同的是所用烯丙基磺酸钠溶液未用硫酸中和。所得水溶液的固体含量为22.1%,并且聚合物的K值为9.1(1重量%水溶液)。
加溶物的制备
将2克共聚物称入玻璃烧杯中。然后将药物称入各混合物中以获得如下的过饱和溶液。(如果所称物质溶在介质中,则增加重量直到产生沉降物)。
活性成分的称入量:17-β-雌二醇0.2克;吡罗昔康0.2;克霉唑0.2克;卡马西平0.3克;酮康唑0.25克;灰黄霉素0.25克;桂益嗪0.25克。
然后加入pH值为7.0的磷酸盐缓冲剂直到加溶剂和磷酸盐缓冲剂存在的重量比达到1:10。使用磁力搅拌器将该混合物在20℃下搅拌72小时。然后存放至少1小时。过滤混合物,然后采用光度测量法测定,并确定活性成分的含量。
固溶体的制备:一般步骤
将重量比为1:1的活性成分和聚合物(每种2克)称入合适的玻璃容器中,然后加入16毫升二甲基甲酰胺作为溶剂,制得聚合物-活性成分混合物。用磁力搅拌器将混合物在20℃下搅拌24小时。然后用120μm刮刀将溶液施加到玻璃板上。将此板在通风橱下室温干燥0.5小时,然后在干燥箱中于50℃和10毫巴下再干燥0.5小时以定量除去溶剂。随后目视检查样品。如果薄膜为透明且活性成分在7天后不结晶,则评定该活性成分已稳定溶于聚合物中(在表1中指示为:50%溶解)。如果活性成分含量为50重量%时未得到固溶体,则以活性成分加载量为33重量%重复实验(在表中指示为:33%溶解)。本发明的共聚物表现出总体较大的形成固溶体能力。
表:固溶体稳定性
共聚物 | 卡马西平 | 雌二醇 | 吡罗昔康 | 克霉唑 |
实施例1 | 33%溶解 | - | - | 33%溶解 |
实施例2 | 33%溶解 | - | - | 50%溶解 |
实施例4 | 33%溶解 | 33%溶解 | 33%溶解 | 33%溶解 |
实施例5 | 33%溶解 | 33%溶解 | 33%溶解 | 33%溶解 |
实施例6 | 33%溶解 | 33%溶解 | 33%溶解 | 33%溶解 |
Claims (29)
1.共聚物作为微水溶性物质的加溶剂的用途,所述共聚物通过如下单体的自由基引发共聚获得:
a)80-99.5重量%醋酸乙烯酯和
b)0.5-20重量%含磺酸盐基团的单烯键不饱和单体。
2.根据权利要求1所述的用途,其中使用ω-烯烃-1-磺酸或丙烯酸或甲基丙烯酸的磺基烷基酯作为单体b)。
3.根据权利要求1或2所述的用途,其中所述共聚物从如下单体获得:
a)85-98重量%醋酸乙烯酯,
b)2-15重量%至少一种含磺酸盐基团的单烯键不饱和单体。
4.根据权利要求1-3任一项所述的用途,其中所述单体b)以其盐的形式使用。
5.根据权利要求1-4任一项所述的用途,其中所述共聚物包含丙烯酸或甲基丙烯酸的磺基丙基酯作为单体b)。
6.根据权利要求1-5任一项所述的用途,其中所述共聚物包含乙烯基磺酸盐作为单体b)。
7.根据权利要求1-6任一项所述的用途,其中所述共聚物包含烯丙基磺酸盐作为单体b)。
8.根据权利要求1-7任一项所述的用途,其中所述共聚物包含2-甲基丙烯磺酸盐作为单体c)。
9.根据权利要求1-8任一项所述的用途,其中所述共聚物的K值为4-25。
10.根据权利要求1-9任一项所述的用途,其中所述微水溶性物质为生物活性物质。
11.根据权利要求1-10任一项所述的用途,其用于生产治疗疾病的药物组合物。
12.根据权利要求1-10任一项所述的用途,其用于化妆品制剂。
13.根据权利要求1-10任一项所述的用途,其用于农业化学制剂。
14.根据权利要求1-10任一项所述的用途,其用于饮食补充剂或饮食组合物。
15.根据权利要求1-10任一项所述的用途,其用于食品。
16.根据权利要求1-10任一项所述的用途,其用于着色剂制剂。
17.一种微水溶性物质的制剂,其包含作为加溶剂的共聚物,所述共聚物通过如下单体的自由基引发共聚获得:
a)85-98重量%醋酸乙烯酯,
b)2-15重量%至少一种含磺酸盐基团的单烯键不饱和单体。
18.根据权利要求17所述的制剂,其中所述微水溶性物质以固溶体形式存在于共聚物中。
19.根据权利要求17或18所述的制剂,其包含作为微水溶性物质的生物活性物质。
20.根据权利要求17-19任一项所述的制剂,其包含作为微水溶性生物活性物质的活性药物成分。
21.根据权利要求20所述的制剂,其形式为口服剂型。
22.根据权利要求17-20任一项所述的制剂,其包含作为微水溶性生物活性物质的化妆品活性成分。
23.根据权利要求17-19任一项所述的制剂,其包含作为微水溶性生物活性物质的农业化学活性成分。
24.根据权利要求17-19任一项所述的制剂,其包含作为微水溶性生物活性物质的饮食补充剂或饮食活性成分。
25.根据权利要求17或18所述的制剂,其包含作为微水溶性物质的着色剂。
26.一种通过自由基引发共聚制备醋酸乙烯酯和含磺酸盐基团的单体的共聚物的方法,其中首先在微水溶性自由基引发剂的存在下进行聚合,然后在水溶性自由基引发剂的存在下进行后聚合。
27.一种共聚物,其通过如下单体的自由基引发共聚获得:
a)85-98重量%醋酸乙烯酯
b)2-15重量%至少一种丙烯酸或甲基丙烯酸的磺基烷基酯。
28.根据权利要求27所述的共聚物,其包含丙烯酸或甲基丙烯酸的磺基丙基酯作为单体b)。
29.根据权利要求27或28所述的共聚物,其中所述单体b)以其钾盐的形式使用。
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CN107793520A (zh) * | 2016-09-07 | 2018-03-13 | 中国石油化工股份有限公司 | 一种制备聚乙烯‑聚乙酸乙烯酯弹性体无皂微乳液的方法 |
CN107920528A (zh) * | 2015-09-04 | 2018-04-17 | 住友化学株式会社 | 组合物、组合物的制造方法和农药组合物 |
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US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
BRPI0813749A2 (pt) * | 2007-07-06 | 2015-01-06 | Basf Se | Uso de homo- copolímeros p, composição de composto ativo, preparação de composto ativo aquosa, uso de uma composição de composto ativo, processo para a preparação de uma dispersão aquosa de compostos ativos orgânicos fracamente solúveis em água, e, dispersão aquosa de compostos ativos orgânicos fracamente solúveis em água |
CA2707282A1 (en) * | 2007-12-12 | 2009-06-18 | Basf Se | Salts of active ingredients with polymeric counterions |
US20090163449A1 (en) * | 2007-12-20 | 2009-06-25 | Eastman Chemical Company | Sulfo-polymer powder and sulfo-polymer powder blends with carriers and/or additives |
CN103158206A (zh) * | 2013-03-19 | 2013-06-19 | 太仓市佳玲塑料制品有限公司 | 一种醋酸乙烯造粒的制备工艺 |
US11254620B2 (en) * | 2013-08-05 | 2022-02-22 | Verdesian Life Sciences U.S., Llc | Micronutrient-enhanced polymeric seed coatings |
US10647793B2 (en) | 2014-03-28 | 2020-05-12 | Synthomer (Uk) Limited | Use of a sulphur or phosphorous-containing polymer as a processing aid in a polyvinyl chloride polymer composition |
WO2015145174A1 (en) | 2014-03-28 | 2015-10-01 | Synthomer (Uk) Limited | Secondary suspending agent for suspension polymerisation reaction |
GB201405624D0 (en) | 2014-03-28 | 2014-05-14 | Synthomer Uk Ltd | Method of making a branched polymer, a branched polymer and uses of such a polymer |
CN107921000B (zh) | 2015-08-21 | 2021-03-30 | 巴斯夫欧洲公司 | 活性成分与聚合抗衡离子的盐 |
GB201918030D0 (en) | 2019-12-09 | 2020-01-22 | Synthomer Uk Ltd | Improvements in, or relating to, binders and/or coatings |
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CN107920528A (zh) * | 2015-09-04 | 2018-04-17 | 住友化学株式会社 | 组合物、组合物的制造方法和农药组合物 |
CN107793520A (zh) * | 2016-09-07 | 2018-03-13 | 中国石油化工股份有限公司 | 一种制备聚乙烯‑聚乙酸乙烯酯弹性体无皂微乳液的方法 |
CN107793520B (zh) * | 2016-09-07 | 2020-10-23 | 中国石油化工股份有限公司 | 一种制备聚乙烯-聚乙酸乙烯酯弹性体无皂微乳液的方法 |
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