CN1110509C - 在制备水不溶性物质中n－乙烯基吡咯烷酮共聚物的用途 - Google Patents
在制备水不溶性物质中n－乙烯基吡咯烷酮共聚物的用途 Download PDFInfo
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- CN1110509C CN1110509C CN98108749A CN98108749A CN1110509C CN 1110509 C CN1110509 C CN 1110509C CN 98108749 A CN98108749 A CN 98108749A CN 98108749 A CN98108749 A CN 98108749A CN 1110509 C CN1110509 C CN 1110509C
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/911—Emulsifying agents
Abstract
下列物质共聚物的用途，用作水不溶性物质制剂中的表面活性物质：A)60-99摩尔%N-乙烯基吡咯烷酮，和B)1-40摩尔%选自以下组的单体：b1)一烯属不饱和C3-C8羧酸的C8-C30烷基酯，b2)N-烷基-或N，N-二烷基取代的丙烯酸或甲基丙烯酸的酰胺，其中烷基是C8-C18烷基，或b3)脂族C8-C30羧酸的乙烯酯，或这些单体的混合物。
Description
本发明涉及下列物质的共聚物在制备水不溶性物质中作为表面活性物质的用途：a)60-99摩尔％N-乙烯基吡咯烷酮，和b)1-40摩尔％选自以下组的单体：
b1)一烯属不饱和C3-C8羧酸的C8-C30烷基酯
b2)N-烷基-或N，N-二烷基取代的丙烯酸或甲基丙烯酸的酰胺，其中烷基C8-C18烷基是，或
b3)脂族C8-C30羧酸的乙烯酯，或这些单体的混合物，以及涉及含有这些共聚物的制剂。优选的用途是在药物或化妆品制剂中使用。
DE-A2514100公开了乙烯基吡咯烷酮和长链甲基丙烯酸烷基酯的共聚物和乙烯基吡咯烷酮，乙酸乙烯酯和长链甲基丙烯酸烷基酯的三元聚合物用作油包水乳化液中的乳化剂。所述共聚物中的乙烯基吡咯烷酮与羧酸酯的摩尔比为1∶1-1∶20，优选1∶1.5-1∶10。
所述聚合物作为水包油乳化液中乳化剂的用途尚属未知。同样乙烯基吡咯烷酮/羧酸酯摩尔比大于1∶1的共聚物和三元聚合物在化妆品或药物制剂中的用途也未被公开。
药物和化妆品添加剂并不总能充分地溶解在水中。添加剂在水中不适宜的溶解度是指不能获得均匀并具有令人满意外观的制剂，并且在许多情况下也指不能达到最佳的所需效果。因此，必须要用亲水亲油辅助物质例如表面活性剂来加溶这种类型的添加剂。以这种方法来提高添加剂的生物利用率和效果。
本发明的一个目的是提供用于药物、化妆品或其它水不溶性添加剂或不能均匀分散物质的物质的加溶剂，并由此使它们能够充分地在体内吸收和分布。另一个意图是提供能够稳定水包油乳化液的物质。
我们发现采用开头限定的共聚物能够实现这个目的。
含N-乙烯基吡咯烷酮的聚合物通过游离基聚合相应的单体来制备，所述单体在各种情况下含有至少60摩尔％的乙烯基吡咯烷酮。
合适的共聚用单体B)是选自以下组b1)-b3)中一种的至少1摩尔％，小于40摩尔％，优选10-20摩尔％的单体或这些共聚用单体的混合物。
合适的单体b1)是一乙烯基化不饱和C3-C8羧酸的C8-C30烷基酯。合适羧酸的实例是丙烯酸、甲基丙烯酸、二甲基丙烯酸、乙基丙烯酸(ethacrylic acid)、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、中康酸或衣康酸，丙烯酸和/或甲基丙烯酸是优选的。合适的烷基包括环烷基。优选使用C8-C18烷基酯。合适单体的实例是丙烯酸辛酯、丙烯酸2-乙基己酯、甲基丙烯酸2-乙基己酯、丙烯酸壬酯、丙烯酸癸酯、丙烯酸十二酯、丙烯酸十四酯、丙烯酸十六酯、丙烯酸十八酯、丙烯酸油酯、丙烯酸二十二酯、甲基丙烯酸己酯、甲基丙烯酸辛酯、甲基丙烯酸壬酯、甲基丙烯酸癸酯、甲基丙烯酸十二酯、甲基丙烯酸十四酯、甲基丙烯酸十六酯、甲基丙烯酸十八酯、甲基丙烯酸油酯、甲基丙烯酸二十二酯或丙烯酸叔丁基环己酯。
此外，合适的单体b2)也是N-烷基-或N，N-二烷基取代的丙烯酸或甲基丙烯酸的羧酰胺(carboxamide)，其中烷基是C8-C18烷基或环烷基，例如N-硬脂基丙烯酰胺、N-硬脂基甲基丙烯酰胺、N-辛基丙烯酰胺、N，N-二辛基丙烯酰胺、N，N-二辛基甲基丙烯酰胺、N-十六烷基丙烯酰胺、N-十六烷基甲基丙烯酰胺、N-十二烷基丙烯酰胺、N-十二烷基甲基丙烯酰胺、N-十四烷基丙烯酰胺、2-乙基己基丙烯酰胺。在N，N-二烷基酰胺的情况下，C8-和C9-烷基是优选的。
其它合适的单体B是脂族羧酸(C8-C30羧酸)的乙烯酯。优选使用C8-C18羧酸的乙烯酯，例如辛酸、壬酸、癸酸、十一酸、月桂酸、十三酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸或二十二酸或油酸的乙烯酯。
当然，也可使用两种或多种羧酸酯、羧酰胺或乙烯酯的混合物，只要这些共聚用单体所占比例的总量不超过40摩尔％就行。
此外，共聚用单体C)可以使用下列共聚单体(或者是它们的混合物)(0-39摩尔％，优选0-20摩尔％，更优选0-10摩尔％)。
它们是具有3-8个碳原子的一烯属不饱和羧酸例如丙烯酸、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、乙烯基乙酸、巴豆酸、富马酸、中康酸或衣康酸。这些单体组中优选使用丙烯酸、甲基丙烯酸、马来酸或所述羧酸的混合物。一烯属不饱和羧酸可以在共聚合中以游离酸的形式使用，必要时以酐或部分或全部中和的形式使用。这些单体最好用碱金属或碱土金属的碱、氨或胺来中和，实例包括氢氧化钠溶液、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、气态氨或氨水、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。
其它合适共聚用单体C)的实例是上述羧酸的C1-C4烷基酯、酰胺和腈，例如丙烯酸甲酯、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、马来酸一甲酯、马来酸二甲酯、马来酸一乙酯、马来酸二乙酯、丙烯酰胺、甲基丙烯酰胺、N，N-二甲基丙烯酰胺、N-叔丁基丙烯酰胺、丙烯腈、甲基丙烯腈、二甲基氨基乙基丙烯酸酯、二乙基氨基乙基丙烯酸酯、二乙基氨基乙基甲基丙烯酸酯和上述单体与羧酸或无机酸的盐和季铵化产物。
其它合适的共聚用单体C)是丙烯酰氨基乙醇酸、乙烯磺酸、烯丙基磺酸、甲基烯丙基磺酸、苯乙烯磺酸、3-磺丙基丙烯酸酯、3-磺丙基甲基丙烯酸酯和丙烯酰氨甲基丙基磺酸和含膦酰基单体例如乙烯基膦酸、烯丙基膦酸和丙烯酰氨甲基丙基膦酸。
其它合适的共聚化合物C)是N-乙烯基己内酰胺、N-乙烯基咪唑、N-乙烯基-2-甲基咪唑、N-乙烯基-4-甲基咪唑、二烯丙基氯化铵、乙酸乙烯酯和丙酸乙烯酯。也可使用所述单体的混合物。
共聚用单体可用聚合条件下形成游离基的化合物通过诸如溶液、沉淀或反悬浮液聚合的已知方法来制备。
聚合通常是在30-200，优选40-110℃下进行。合适引发剂的实例是偶氮和过氧化合物，和通常的氧化还原引发剂体系，例如过氧化氢和还原化合物的混合物，例如亚硫酸钠、亚硫酸氢钠、甲醛合次硫酸氢钠和肼。
共聚物具有的K值至少为7，至多为130，优选10-100，更优选10-20。K值用H.Fikentscher，《纤维素化学》13(1932)58-64和71-74的方法，在25℃下浓度为0.1-5％(取决于K值)的水溶液中测定。
根据本发明，所述共聚物适用于作为制剂中的表面活性物质，所述制剂含有一种或多种水不溶性物质作为主要组分。用于本发明目的的水不溶性物质是在使用条件下在水中明显难溶的物质。这是指在使用条件下溶解物质的量是不充分的。因此，水不溶性物质在常规条件下与水不混溶，或者不能自发地形成均匀的水相。用于本发明目的的水不溶性物质特指药物或化妆品添加剂，但是也包括在农作物保护组合物中使用的添加剂、此外还指兽医医用添加剂、诸如用于膳食食品的食品添加剂、食品着色剂或用于家畜食物的添加剂。此外，共聚物可用来提高添加剂的生物利用率，而这种添加剂具有低的溶解度或是难溶的，或者作为含水介质的加溶剂或用来稳定分散水溶液例如悬浮液或油包水乳化液。
在药物制剂领域中，共聚物适合于以口服给药的固态药物形式、栓剂、阴道给药形式、经粘膜的给药的药物、眼药或耳药、药物溶液、肺部给药形式、药用指甲清漆(medicinal nail varnishes)、药用护发组合物、肠胃外给药的药物形式、肠胃外消化制剂、或经皮下的形式使用，以提高皮肤对添加剂的吸收性。经皮下的形式除了乳油、软膏、凝胶或洗剂外还可以是膏药例如烟碱膏药或例如给药甾类激素的膏药、硝基化合物、止痛药、羟基羧酸、纤维素A酸或其它视网膜样、抗真菌、抗感染、抑制病毒复制剂、α-或β阻滞物。
根据本发明，化妆品制剂是用于护肤、护发、护指甲或口腔卫生的组合物。例如共聚物适合于加溶或稳定芳香油、精油、香精或油浴添加剂。
用于农作物保护的制剂含有农药、除草剂、杀菌剂或杀虫剂，尤其包括那些用作喷雾或洒水混合物的制剂。
共聚物还适合于食品工业部门，例如作为低溶解性食品着色的保护胶体或分散助剂例如类胡罗卜素。
同样，共聚物可用作乳化液或悬浮液聚合或照相制剂或有机调色剂中的保护胶体。
共聚物的用量按制剂的总量计为0.05-20％，优选0.1-10％，特别优选0.5-5％。制剂可以是液体，优选水溶液的制剂或者是固体或半固体制剂。它们除了共聚物和水不溶性物质外还含有通常用于特定用途的辅剂，其用量为用于该目的的常规量。
实施例1-4
用下列实施例提及的共聚物试验对添加剂苯甲二氮的加溶作用。使用1％(重量)聚合物水溶液。
| 聚合物 | K值(1％水中) | 加溶作用 |
| 实施例1N-乙烯基吡咯烷酮/丙烯酸十八烷酯共聚物(90∶10重量％) | 20.0 | 185μg/ml苯甲二氮 |
| 实施例2N-乙烯基吡咯烷酮/甲基丙烯酸十六烷酯共聚物(80∶20重量％) | 18.3 | 205μg/ml苯甲二氮 |
| 实施例3N-乙烯基吡咯烷酮/乙烯基己内酰胺/十二烷基甲基丙烯酰胺三元聚合物(60∶20∶20重量％) | 10.9 | 200μg/ml苯甲二氮 |
| 实施例4N-乙烯基吡咯烷酮/硬酯酸乙烯酯共聚物(90∶10重量％) | 25 | 195μg/ml苯甲二氮 |
Claims (4)
1.水不溶性物质的制剂，其中包括下列物质的共聚物作为表面活性物质A)60-99摩尔％N-乙烯基吡咯烷酮，和B)1-40摩尔％选自以下组的单体：
b1)一烯属不饱和C3-C8羧酸的C8-C30烷基酯，
b2)N-烷基-或N，N-二烷基取代的丙烯酸或甲基丙烯酸的酰胺，其中烷基是C8-C18烷基，或
b3)脂族C8-C30羧酸的乙烯酯。
2.根据权利要求1的水不溶性物质的制剂，其中所述共聚物包括0-39摩尔％其它游离基共聚单体C)。
3.水不溶性药物添加剂的制剂，其中包括权利要求1中的共聚物作为表面活性物质。
4.水不溶性化妆品添加剂的制剂，其中包括权利要求1中的共聚物作为表面活性物质。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19719187A DE19719187A1 (de) | 1997-05-07 | 1997-05-07 | Verwendung von Copolymerisaten des N-Vinyl-pyrrolidons in Zubereitungen wasserunlöslicher Stoffe |
| DE19719187.8 | 1997-05-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1198441A CN1198441A (zh) | 1998-11-11 |
| CN1110509C true CN1110509C (zh) | 2003-06-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98108749A Expired - Fee Related CN1110509C (zh) | 1997-05-07 | 1998-05-06 | 在制备水不溶性物质中n－乙烯基吡咯烷酮共聚物的用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6075107A (zh) |
| EP (1) | EP0876819B1 (zh) |
| JP (1) | JPH10314571A (zh) |
| CN (1) | CN1110509C (zh) |
| DE (2) | DE19719187A1 (zh) |
| ES (1) | ES2206782T3 (zh) |
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| DE19753298A1 (de) | 1997-12-01 | 1999-06-02 | Basf Ag | Verfahren zur Herstellung von festen Dosierungsformen |
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| DE19908184A1 (de) | 1999-02-25 | 2000-08-31 | Basf Ag | Verfahren zur Herstellung wässriger Dispersionen von Copolymerisaten aus hydrophilen und hydrophoben Monomeren sowie daraus erhältliche Copolymerisate und deren Anwendungen |
| US6479076B2 (en) * | 2001-01-12 | 2002-11-12 | Izhak Blank | Nicotine delivery compositions |
| DE10108387A1 (de) * | 2001-02-21 | 2002-08-29 | Basf Ag | Kosmetisches oder pharmazeutisches Mittel |
| DE10217440A1 (de) | 2002-04-18 | 2003-11-06 | Basf Ag | Verwendung hydrophob modifizierter Copolymere auf Basis von N-Vinylmonomeren zur Herstellung von Membranen |
| GB0229147D0 (en) | 2002-12-13 | 2003-01-15 | Unilever Plc | Polymers and laundry detergent compositions containing them |
| GB0229146D0 (en) * | 2002-12-13 | 2003-01-15 | Unilever Plc | Polymers and laundry detergent compositions containing them |
| ITMI20022673A1 (it) * | 2002-12-18 | 2004-06-19 | 3V Sigma Spa | Composizioni detergenti per la pulizia. |
| DE102004020767A1 (de) * | 2004-04-27 | 2005-11-24 | Basf Ag | Oberflächenmodifizierte Metalloxide, Verfahren zur Herstellung und deren Verwendung in kosmetischen Zubereitungen |
| RU2378293C2 (ru) * | 2004-06-08 | 2010-01-10 | Басф Акциенгезельшафт | Амфифильные полимерные композиции и их применение |
| JP4876073B2 (ja) * | 2004-08-03 | 2012-02-15 | ティシュームド リミテッド | 組織接着性材料 |
| DE102004040104A1 (de) * | 2004-08-18 | 2006-02-23 | Basf Ag | Verwendung von amphiphilen Copolymerisaten als Solubilisatoren |
| WO2006050115A1 (en) * | 2004-10-28 | 2006-05-11 | Bayer Healthcare Llc | Hydrogel composition |
| DE102004058952A1 (de) * | 2004-12-07 | 2006-06-14 | Basf Ag | Verfahren zur Herstellung wässriger Sekundärdispersionen von in Wasser nicht löslichen Polymeren |
| EP1879551A2 (de) | 2005-02-21 | 2008-01-23 | Basf Aktiengesellschaft | Wirkstoffzusammensetzung die wenigstens ein stickstoffatomhaltiges, hyperverzweigtes polymer enthält |
| DE102005025972A1 (de) * | 2005-06-03 | 2006-12-07 | Basf Ag | Oberflächenmodifizierte Metalloxide, Verfahren zur Herstellung und deren Verwendung in kosmetischen Zubereitungen |
| DE102005036328A1 (de) * | 2005-07-29 | 2007-02-01 | Basf Ag | Copolymere auf Basis von N-Vinylpyrrolidon und verzweigten aliphatischen Carbonsäuren und deren Verwendung als Solubilisatoren |
| EP1915407A2 (de) * | 2005-08-11 | 2008-04-30 | Basf Se | Copolymere auf basis von n-vinylcaprolactam und deren verwendung als solubilisatoren |
| DE102005053066A1 (de) | 2005-11-04 | 2007-05-10 | Basf Ag | Verwendung von Copolymeren als Solubilisatoren für in Wasser schwerlöslichen Verbindungen |
| WO2007065846A2 (de) * | 2005-12-09 | 2007-06-14 | Basf Se | Verwendung von polyvinyllactam-polyoxyalkylen-blockcopolymeren als solubilisatoren für in wasser schwerlösliche verbindungen |
| JP2009525109A (ja) * | 2006-02-03 | 2009-07-09 | ティシューメッド リミテッド | 組織接着材料 |
| EA019366B1 (ru) | 2006-11-13 | 2014-03-31 | Басф Се | Применение блок-сополимеров на основе виниллактамов и винилацетата в качестве ингибиторов кристаллизации, препарат агрохимических компонентов, включающий поливиниллактам-поливинилацетатный блок-сополимер, способ борьбы с нежелательным нападением насекомых или клещей и/или борьбы с фитопатогенными грибами и способ борьбы с нежелательным ростом растений |
| JP5323715B2 (ja) * | 2006-11-30 | 2013-10-23 | ビーエーエスエフ ソシエタス・ヨーロピア | １−ビニル−２−ピロリジノンコポリマーを含む農薬製剤 |
| EP2173781A1 (de) * | 2007-07-26 | 2010-04-14 | Basf Se | Verfahren zur herstellung von durch pfropfpolymerisation in lösung erhaltenen copolymeren auf basis von polyethern in fester form |
| EP2022805A3 (en) | 2007-08-03 | 2009-02-25 | Basf Se | Copolymers based on N-vinyllactams and olefins as their use as solubilizers for slightly water-soluble compounds |
| US20100204045A1 (en) * | 2007-09-27 | 2010-08-12 | Basf Se | Systemicity Enhancers |
| US20100104610A1 (en) * | 2008-10-01 | 2010-04-29 | Dueva-Koganov Olga V | Color cosmetics comprising a random terpolymer |
| EP2429286B1 (de) * | 2009-05-11 | 2015-08-19 | Basf Se | Polymere zur erhöhung der bodenbeweglichkeit von schwer löslichen insektiziden |
| BRPI1010550B1 (pt) | 2009-05-13 | 2019-11-05 | Basf Se | formas de dosagem, e, processo para a produção de preparações para formas de dosagem de substâncias ativas fracamente solúveis em água |
| WO2011086073A2 (en) | 2010-01-14 | 2011-07-21 | Basf Se | Water-resistant cosmetic formulations comprising a hydrophobically modified vinylpyrrolidone copolymer |
| WO2013149925A1 (en) * | 2012-04-04 | 2013-10-10 | Basf Se | Agroformulation comprising copolymer of vinyllactam, n-alkyl acrylamide, and alkyl (meth)acrylate |
| WO2015093924A1 (es) * | 2013-12-19 | 2015-06-25 | CASTRO ALDRETE, Jorge Issac | Vehículo para la administración de compuestos farmacéuticos |
| AU2016355475A1 (en) * | 2015-11-20 | 2018-06-07 | Isp Investments Llc | Fragrance delivery composition comprising copolymers of acryloyl lactam and alkylmethacrylates, process for preparing the same, and method of use thereof |
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| DE3390556T1 (de) * | 1983-12-01 | 1985-11-14 | Vsesojuznyj naučno-issledovatel'skij i ispytatel'nyj institut medicinskoj techniki, Moskau/Moskva | Material von Bindeelementen für weiche Gewebe und innere Organe |
| DE4438706A1 (de) * | 1994-10-29 | 1996-05-02 | Basf Ag | Lösliche Copolymerisate für die Haarkosmetik |
-
1997
- 1997-05-07 DE DE19719187A patent/DE19719187A1/de not_active Withdrawn
-
1998
- 1998-04-23 EP EP98107386A patent/EP0876819B1/de not_active Expired - Lifetime
- 1998-04-23 ES ES98107386T patent/ES2206782T3/es not_active Expired - Lifetime
- 1998-04-23 DE DE59809317T patent/DE59809317D1/de not_active Expired - Lifetime
- 1998-05-06 CN CN98108749A patent/CN1110509C/zh not_active Expired - Fee Related
- 1998-05-06 JP JP10123417A patent/JPH10314571A/ja active Pending
- 1998-05-07 US US09/073,856 patent/US6075107A/en not_active Expired - Lifetime
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| US5132417A (en) * | 1988-12-15 | 1992-07-21 | Basf Aktiengesellschaft | Copolymer based on tert-butyl acrylate or methacrylate |
| US5008321A (en) * | 1988-12-20 | 1991-04-16 | Basf Aktiengesellschaft | Preparation of stable water-in-oil emulsions of hydrolyzed polymers of N-vinylamides and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59809317D1 (de) | 2003-09-25 |
| JPH10314571A (ja) | 1998-12-02 |
| ES2206782T3 (es) | 2004-05-16 |
| DE19719187A1 (de) | 1998-11-12 |
| EP0876819B1 (de) | 2003-08-20 |
| CN1198441A (zh) | 1998-11-11 |
| EP0876819A1 (de) | 1998-11-11 |
| US6075107A (en) | 2000-06-13 |
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