CN114828807B - 与壳聚糖交联的聚脲胶囊 - Google Patents
与壳聚糖交联的聚脲胶囊 Download PDFInfo
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- CN114828807B CN114828807B CN202180006595.XA CN202180006595A CN114828807B CN 114828807 B CN114828807 B CN 114828807B CN 202180006595 A CN202180006595 A CN 202180006595A CN 114828807 B CN114828807 B CN 114828807B
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- chitosan
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- aqueous phase
- microcapsules
- core
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Abstract
描述了形成包封有益剂的聚脲和壳聚糖微胶囊的改进方法。所述方法包括形成水相,包括在pH为6.5或更低的酸性介质中水解壳聚糖较长时间,并与多异氰酸酯组合。水解壳聚糖与多异氰酸酯的反应产物产生的微胶囊具有改进释放特性和按OECD测试方法301B具有增强的降解特性。
Description
技术领域
本发明涉及胶囊生产方法和通过所述方法生产的微胶囊。
背景技术
微胶囊化的各种方法以及示例性方法和材料在如下文献中有述:Schwantes(US6,592,990)、Nagai等人(US 4,708,924)、Baker等人(US 4,166,152)、Wojciak(US 4,093,556)、Matsukawa等人(US 3,965,033)、Matsukawa(US 3,660,304)、Ozono(US 4,588,639)、Irgarashi等人(US 4,610,927)、Brown等人(US 4,552,811)、Scher(US 4,285,720)、Shioi 等人(US 4,601,863)、Kiritani等人(US 3,886,085)、Jahns等人(US 5,596,051和US 5,292,835)、Matson(US 3,516,941)、Chao(US 6,375,872)、Foris等人(US 4,001,140;US 4,087,376;US 4,089,802和US 4,100,103)、Greene等人(US 2,800,458;2,800,457和US 2,730,456)、Clark(US 6,531,156)、Saeki等人(US 4,251,386和US 4,356,109),Hoshi等人(US 4,221,710)、Hayford(US 4,444,699)、Hasler等人(US 5,105,823)、Stevens(US 4,197,346)、Riecke(US 4,622,267)、Greiner等人(US 4,547,429)和Tice等人(US 5,407,609),以及由Herbig在Kirk-Othmer Encyclopedia of Chemical Technology V.16第438-463页题为“Microencapsulation”的章节中所教导的。
本申请中提到的每个专利均作为参考引入,引入程度足以提供关于微胶囊化方法和材料的引导。
Jabs等人的US 4,847,152教导了具有聚脲壁的微胶囊。所述壁为具有异氰酸酯反应基团的芳族异氰酸酯的反应产物。所述异氰酸酯反应基团可以包括二胺和多胺,如N-羟基乙基乙二胺、亚乙基-1,2-二胺。
Hotz等人的美国专利公开No.2013/0089590教导了具有聚脲壁的香料微胶囊。所述壁为至少两种双官能的异氰酸酯与双官能的胺的反应产物。
在EP 1693104中Maruyyama公开了具有由多官能异氰酸酯与多官能胺缩聚获得的聚氨酯或聚脲壁的微胶囊。
US 9,816,059描述了聚脲胶囊,所述胶囊包封油芯,其中所述聚脲为多官能异氰酸酯与多官能胺的反应产物。所述多官能胺可以包括己二胺和其它胺,包括壳聚糖。但壳聚糖作为稳定剂、作为多官能胺、作为涂料提及,并没有任何引导或示例给出如何处理这种难以处理的材料。
壳聚糖是一种多糖,在微胶囊化方法中是一种很难使用的材料。壳聚糖通常在pH高于7的水中不溶,而pH低于约6.5时是阳离子。壳聚糖溶于低pH酸性溶液如盐酸、乳酸、丙酸、琥珀酸、乙酸、柠檬酸和磷酸中,形成很难处理的粘稠溶液,但在pH高于7时通常不溶。当pH值低于4时,壳聚糖的氨基促进静电排斥和聚合物膨胀。在酸性溶液中,据信游离的胺基与相邻的氧基形成氢键。
溶解的多糖具有带正电荷的-NH3 +基团并粘附于阴离子表面。壳聚糖与聚阴离子形成聚集体并与重金属螯合。
本领域需要在如下方面具有改进特性的聚脲型微胶囊:更好的沉积效率、按较低游离油测量的较低泄漏量以及当pH小于约7时具有阳离子电荷。如果壳聚糖可用作可溶***联剂,则有可能成为改进的聚脲壁材料。
本发明通过提出与壳聚糖交联的改进聚脲微胶囊克服了现有技术的上述缺陷。壳聚糖发生水解,从而使壳聚糖甚至在pH大于5时可溶,从而使其可用于微胶囊化过程,如界面包封。
虽然现有技术中通常提到壳聚糖在微胶囊化中是形成壁材料的可能组分,但很少有关于如何实际应用这种难以处理的材料的教导。
壳聚糖通常不溶于水、碱和大多数有机溶剂。即使在酸性的低pH条件下,溶解度也通常小于2wt%。所述组合物粘稠、难以处理和需要大幅度稀释。壳聚糖浓度小于2wt%使得材料不适于界面微胶囊化。
壳聚糖在较高pH下不溶,而在胶囊形成条件下形成胶囊通常包括pH为7或9或甚至更碱性的条件,这种情况下壳聚糖基本上是不溶的粘稠物质,不适合界面包封。
需要壳聚糖浓度更高的壳聚糖聚脲组合物,以克服处理壳聚糖的技术难题,并在水相中提供大于2wt%的有用浓度,从而成功地形成壳聚糖-脲聚合物壳。
虽然如Lei等人在美国专利申请no.2013/0330292中提到将壳聚糖用作交联剂来制备聚脲胶囊,但Lei没有提供关于如何应用壳聚糖的任何描述。壳聚糖只在低pH下可溶,在更高pH下不溶。当pH升高时,壳聚糖将从溶液中沉淀出来。另外,由于分子量高,壳聚糖是一种极难用作交联剂的材料。
Bulgarelli等人的WO 2019063515试图通过以固体形式添加壳聚糖来克服Lei的缺点。Bulgarelli提到在乳液的水相中添加壳聚糖。当反应温度达到80℃时,加入未质子化的壳聚糖。权利要求中称以固体形式加入壳聚糖,但Bulgarelli没有提供关于如何有效溶解固体壳聚糖的实例。已知壳聚糖在碱性pH下或甚至在pH大于5时会沉淀。
聚脲微胶囊在某些应用中因不含甲醛而有利。迄今为止,所述聚脲体系的机械特性还没有在某些挑战性应用如洗涤剂、清洁剂、含表面活性剂的组合物、改性剂或其它材料中所需的芯保持性能,导致在长期贮存后倾向于负面影响胶囊的性能。对本领域来说,成功结合以比目前可实现浓度更高的壳聚糖、不需要附加交联剂或表现出较少泄漏的聚脲壳聚糖是一种进步。所形成的这种组合物改进的贮存稳定性、降低的泄漏和降解将是有益的。
附图说明
图1和图2为按本发明制备的微胶囊的zeta电势图线。
发明内容
本发明公开了形成多种微胶囊的组合物和方法,所述微胶囊包括芯和包围所述芯的壳,所述方法包括:在pH为6.5或更低的酸性介质中在温度至少60℃下水解壳聚糖至少1小时。通过上述方法形成水解壳聚糖的水相。另外,通过向油相中溶解或分散至少一种有益剂和至少一种多异氰酸酯而形成油相。有益剂经常可以本身为油相中的油,与多异氰酸酯和有益剂一起溶解,或任选与添加的油一起溶解。通过在高剪切搅拌下混合水相和油相进入过量水相中形成乳液,从而形成水相中分散的油相和有益剂的液滴,而所述液滴包含芯-壳微胶囊的芯。任选地,可以调节乳液的pH为pH 2至pH 6.5。然后通过加热至至少40℃、或甚至至少60℃足够时间固化乳液,以在液滴与水相的界面处形成壳,所述壳为包括多异氰酸酯和水解壳聚糖的反应产物的聚脲,所述壳包围油相和有益剂的液滴。对于许多应用来说,目标液滴尺寸为0.1-80微米,或甚至0.5-50微米。
在另一个实施方案中,首先通过在pH小于6.5如pH为pH 3至pH 6下和在温度至少40℃或甚至至少60℃或甚至至少80℃下水解而处理壳聚糖。水解时间取决于pH和温度,可以很短,但通常为至少1小时,或甚至至少24小时。通过这种处理步骤,在任意实施方案的水解步骤中,壳聚糖脱乙酰化至至少50%或甚至至少75%,或甚至至少80%,或甚至至少85%,或甚至至少92%。理想地,在水解步骤中所述壳聚糖解聚至95千道尔顿(kDa)或更低的平均大小。所形成的壳为聚脲及多异氰酸酯和水解壳聚糖的反应产物,所述多异氰酸酯包括任意的如下物质:异氰酸酯单体、低聚物或预聚物。微胶囊群可以包括含水浆液,或替代地可以喷撒到基质上,或替代地被喷雾干燥,导致在所形成的微胶囊的表面上进一步沉积壳聚糖的聚脲-壳聚糖壳。含水浆液中的未反应壳聚糖如果不丢掉,可以形成在所形成的微胶囊的表面上沉积的进一步的壳聚糖。
在一个实施方案中,微胶囊干燥并在干燥下开裂,从而将芯释放出来。这种实施方案可用于具有香料递送的清洁剂或具有有益剂如农用活性物质的农用试剂中。干燥开裂的干爆型胶囊通过控制反应条件如控制固化时间和控制温度以产生具有薄壁的胶囊而形成。固化温度越高,固化时间越长,可能导致交联密度越高和脆性越大。较薄的壁,如0.1至约300纳米,在干燥时容易变脆。即使在干爆型的实施方案中,本发明的胶囊也表现出较低的泄漏,且在胶囊浆液预干燥过程中更好地保持芯。
在某些实施方案中,相比于多异氰酸酯的量,在聚脲壳中壳聚糖可以为总壳的21-85wt%或甚至90wt%。
在一个特定的实施方案中,本发明方法有可能使得芯-壳微胶囊的聚脲壳中壳聚糖相比于多异氰酸酯的量为总壳的21wt%或更大,更具体地为21-90wt%,或甚至为21-85wt%,或甚至为21-75wt%,或21-55wt%。
在一个替代的实施方案中,本发明的壳聚糖聚脲胶囊有可能形成在聚合物中具有高比例壳聚糖部分的反应聚合物壳。聚合物壳的壳聚糖与脲的重量比可以大于21wt%壳聚糖,或甚至为21-40wt%壳聚糖,或甚至为21-60wt%的壳聚糖,或甚至为25-80wt%或甚至至90wt%的壳聚糖。壳聚糖聚脲微胶囊中这种高壳聚糖重量百分比有可能形成以前利用界面类包封方法无法达到的改进胶囊体系。本发明的方法和组合物不同于基于凝聚的离子型方法,因为本发明的聚合物与聚脲组成单体、低聚物和预聚物共价交联,形成壳聚糖聚脲聚合物壳。
组合物包括芯-壳微胶囊、包含有益剂的芯、包含由异氰酸酯单体、低聚物或预聚物和水解壳聚糖反应形成的聚脲树脂的壳。所述壳聚糖首先在pH 6.5或更低的酸性介质中和至少60℃的温度下水解至少1小时。
在较低pH下,壳聚糖中的游离胺质子化。为了此目的,壳聚糖包括其单体、低聚物、预聚物和聚合物。当壳聚糖质子化时,常规理解是壳聚糖将失去其用作交联剂的能力。壳聚糖在低pH值、通常小于pH 4时,也不再用作乳化剂。
一个令人惊奇的方面是按本发明在低pH下形成的胶囊不仅是在壳聚糖与脲(或多异氰酸酯)的高wt%比下具有低泄漏的紧致胶囊,而且这种胶囊表现出在相对短时间内的可降解特性。相比于由相同或类似材料在不同反应条件形成的胶囊,本发明的微胶囊是可降解的。反应条件的微小差异意外地导致明显不同特性的包封。这种效应对于壳聚糖水解步骤中的反应更为显著,其中将pH调节至约pH 4、或pH2-6、或pH 3-5,但优选pH 3.5-5。对于用在pH 6或更高下水解的壳聚糖制备的胶囊来说,所述胶囊壳按OECD 301(B)方法表现出最小的生物降解。但当胶囊用在pH 5或更低下水解的壳聚糖制备时,胶囊壳在28天内降解超过60%。当水解的pH降低至低于pH 6时,可降解性增加。
在本发明的胶囊形成方法中壳聚糖首先在酸性条件(pH 6.5或更低)下水解。任选地,壳聚糖在pH为2-6.5、或甚至pH为4-6下水解。这产生了具有水溶性的脱乙酰化、解聚后的壳聚糖,但保持了用作乳化剂或不再需要乳化剂的能力,使附加乳化剂变成任选。
可以调节本发明的微胶囊,使其zeta电势在pH 4.5下至少15毫伏(mV),或在pH4.5下甚至至少40mV、或在pH 4.5下甚至至少60mV。这种微胶囊为阳离子型的,和对可用于其中希望沉积到阴离子表面的应用中。在更高的pH下,可以将胶囊制成非离子型或阴离子型。
在一个实施方案中,异氰酸酯单体、低聚物或预聚物与水解壳聚糖的重量比为至多1:10。按多异氰酸酯壳的重量百分比计,壳聚糖可以少至壳的21%和多至95%。基于微胶囊总重,所述壳可以占芯-壳微胶囊的至少5wt%,或甚至至少3wt%、或甚至至少1wt%,和至多15wt%。壳聚糖的脱乙酰度可以为至少75%,或甚至至少85%,或甚至至少92%。在某些实施方案中,芯-壳微胶囊中芯与壳的重量比为至多约99:1,或甚至99.5:0.5。芯-壳微胶囊中的有益剂可以选自香料、农用活性物质、相变材料和这里所述的其它活性物质。所述芯-壳微胶囊的平均颗粒粒度通常为1-100微米。通过在乳化过程中控制液滴尺寸可以获得不同的颗粒粒度。
具体实施方式
本发明涉及一种改进的聚脲-壳聚糖微胶囊。在本发明中,通过在第一步中水解壳聚糖并产生水解壳聚糖的水溶液而成功地制备聚脲-微胶囊。水解壳聚糖可以在酸性至中性pH下用作交联剂,形成芯-壳微胶囊的壳。对于水相来说,pH值为至少2、甚至3或甚至至少4可用于促进水解壳聚糖与异氰酸酯单体的交联。
在本发明中,将水解壳聚糖用作交联剂和乳化剂来制备聚脲胶囊。水解的好处是使壳聚糖脱乙酰和解聚,从而溶解否则难以处理的材料。在本发明中,将壳聚糖加入夹套反应器内的水中,并用酸如浓HCl调整pH为2、或甚至为3-6.5。通过在60分钟内加热至高温如85℃,并在该温度下保持1-1440分钟或更久,水解该混合物中的壳聚糖。然后冷却水相至25℃。任选地,也可以用酶进一步促进或强化脱乙酰,以使壳聚糖解聚或脱乙酰。通过在25℃下在油中溶解异氰酸酯如亚二甲苯基二异氰酸酯(XDI)的三聚物或亚甲基二苯基异氰酸酯(MDI)的聚合物来制备油相。可以应用稀释剂如肉豆蔻酸异丙酯来调节油相的亲水性。然后将油相结合到水相中,并高速研磨以获得目标尺寸。然后在一个或多个加热步骤中固化乳液,如在30分钟内加热至40℃,并在40℃下保持60分钟。时间和温度均为近似值。选择温度和时间,足以在油相液滴与水连续相的界面处形成和固化壳。例如,在60分钟内将乳液加热至85℃,并在85℃下保持360分钟以固化胶囊。然后将浆液冷却至室温。
为此目的,可用于本发明的多异氰酸酯应理解为异氰酸酯单体、异氰酸酯低聚物、异氰酸酯预聚物、或脂族或芳族异氰酸酯的二聚物或三聚物。所有这些单体、预聚物、低聚物或脂族或芳族异氰酸酯的二聚物或三聚物在这里均由术语“多异氰酸酯”涵盖。
多异氰酸酯为脂族或芳族单体、低聚物或预聚物,有用的具有两个或更多个异氰酸酯官能团。例如,多异氰酸酯可以选自用于形成胶囊壁的芳族甲苯二异氰酸酯及其衍生物,或脂族单体、低聚物或预聚物,例如六亚甲基二异氰酸酯及其二聚物或三聚物,或3,3,5-三甲基-5-异氰酰甲基-1-异氰酰环己烷四亚甲基二异氰酸酯。多异氰酸酯可以选自1,3-二异氰酰-2-甲基苯、氢化的MDI、双(4-异氰酰环己基)甲烷、二环己基甲烷-4,4′-二异氰酸酯及它们的低聚物和预聚物。该列表只是示例性的,不用于限制可用于本发明的多异氰酸酯。
可用于本发明的多异氰酸酯包括具有至少两个异氰酸酯基团的异氰酸酯单体、低聚物或预聚物或其二聚物或三聚物。用具有至少三个官能团的多异氰酸酯可以达到最佳交联。
为了本发明的目的,多异氰酸酯被理解为包括具有至少两个异氰酸酯基团且在单体、低聚物或预聚物中包含脂族或芳族部分的任何多异氰酸酯。如果是芳族,则芳族部分可包括苯基、甲苯基、二甲苯基、萘基或二苯基部分,更优选为甲苯基或二甲苯基部分。为此目的,芳族多异氰酸酯可以包括二异氰酸酯衍生物,如缩二脲和多异氰脲酸酯。芳族的多异氰酸酯可以为但不限于亚甲基二苯基异氰酸酯、甲苯二异氰酸酯、四甲基二甲苯胺二异氰酸酯、甲苯二异氰酸酯的多异氰脲酸酯(可由Bayer以商品名RC商购获得)、甲苯二异氰酸酯的三羟甲基丙烷加合物(可由Bayer以商品名/>L75商购获得)、或亚二甲苯基二异氰酸酯的三羟甲基丙烷加合物(可由Mitsui Chemicals以商品名D-110N商购获得)、萘-1,5-二异氰酸酯和亚苯基二异氰酸酯。
脂族的多异氰酸酯被理解为不包含任何芳族部分的多异氰酸酯。优选的是芳族多异氰酸酯,但脂族多异氰酸酯和它们的共混物也是有用的。脂族多异氰酸酯包括六亚甲基二异氰酸酯的三聚物、异佛尔酮二异氰酸酯的三聚物、六亚甲基二异氰酸酯的三羟甲基丙烷加合物(可由Mitsui Chemicals获得)或六亚甲基二异氰酸酯的缩二脲(可由Bayer以商品名N 100商购获得)。
所述胶囊壳也可以应用附加的辅助交联剂如多官能胺和/或多胺如二亚乙基三胺(DETA)、聚乙烯亚胺和聚乙烯基胺强化。
芯
本发明的微胶囊包括有益剂,其包括一种或多种打算包封的组分。有益剂选自多种不同材料,作为示例且不构成限制,如生色团和染料、增香剂、香精、甜味剂、香料、油、脂肪、颜料、清洁油、药品、药用油、香精油、霉菌抑制剂、抗菌剂、粘合剂、相变材料、香味剂、肥料、营养素和除草剂。有益剂和油构成所述芯。所述芯可以是液体或固体。对于环境温度下为固体的芯,对于某些应用,壁材料可以有用地部分包封整个芯,在应用时需要获得聚集体。这种应用可以包括香味释放、清洁组合物、润肤剂、化妆品递送等。当微胶囊芯是相变材料时,应用可以包括在床垫、枕头、床上用品、纺织品、运动设备、医疗设备、建筑产品、结构产品、HVAC、可再生能源、服装、运动场地、电子产品、汽车、航空、鞋、美容护理、洗衣和太阳能中的所述包封材料。
芯构成被微胶囊包封的材料。通常,特别是当芯材料为液体材料时,芯材料与形成微胶囊内壁的一种或多种组合物或用于有益剂的溶剂或分配调节剂组合。如果芯材料可以用作胶囊中的油溶剂,例如用作壁形成材料或有益剂的溶剂或载体,则有可能使芯材料作为主要的被包封材料,或者如果载体本身是有益剂,则可以是全部被包封的材料。但通常情况下,有益剂为0.01-99wt%的胶囊内容物,优选约0.01-65wt%的胶囊内容物,和更优选约0.1-45wt%的胶囊内容物。对于某些应用,即使在痕量下,芯材料也可以是有效的。
当有益剂本身不足以用作油相或溶剂时,特别是对于壁形成材料,油相可以包含合适的载体和/或溶剂。从这个意义上讲,油是任选的,因为有益剂有时本身可以为油。这些载体或溶剂通常为油,优选沸点大于约80℃、具有低挥发度且不易燃。尽管不限于此,但它们优选包含一种或多种酯(优选链长为至多18个碳原子或甚至至多42个碳原子)和/或甘油三酯,如C6-C12脂肪酸和甘油的酯。示例性的载体和溶剂包括但不限于:乙基二苯基甲烷;异丙基二苯基乙烷;丁基二苯基乙烷;苯甲基二甲苯;烷基联苯,如丙基联苯和丁基联苯;邻苯二甲酸二烷基酯,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯、邻苯二甲酸二壬酯和邻苯二甲酸二(十三烷基)酯;2,2,4-三甲基-1,3-戊二醇二异丁酸酯;烷基苯,如十二烷基苯;烷基或芳烷基苯甲酸酯,如苯甲酸苯甲酯;二芳醚;二(芳烷基)醚和芳基芳烷基醚;醚类,如二苯醚、二苯甲基醚和苯基苯甲基醚;液态高级烷基酮(有至少9个碳原子);烷基或芳烷基苯甲酸酯,例如苯甲酸苯甲酯;烷基化萘,如二丙基萘;部分氢化三苯;高沸点的直链或支链烃;烷芳基烃如甲苯、植物和其它作物油,如芥花油、大豆油、玉米油、葵花籽油、棉籽油、柠檬油、橄榄油和松油;由植物油和其它作物油酯交换衍生的脂肪酸的甲酯、油酸的甲酯、植物油的酯,如大豆甲基酯、直链石蜡脂肪烃,和上述物质的混合物。
有用的有益剂包括香精原料,如醇、酮、醛、酯、醚、腈、烯烃、香料、香料增溶剂、精油、相变材料、润滑剂、着色剂、冷却剂、防腐剂、抗菌或抗真菌活性物质、除草剂、抗病毒活性物质、抗菌活性物质、抗氧化剂、生物活性物质、除臭剂、润肤剂、保湿剂、去角质剂、紫外线吸收剂、自愈性组合物、防腐剂、防晒剂、硅油、蜡、烃类、高级脂肪酸、精油、脂类、皮肤冷却剂、维生素、防晒霜、抗氧化剂、甘油、催化剂、漂白颗粒、二氧化硅颗粒、恶臭减少剂、染料、光亮剂、抗菌活性物质、止汗活性物质、阳离子聚合物和它们的混合物。作为描述而非限制,用作有益剂的相变材料可以包括具有13-28个碳原子的链烷烃,各种烃如正二十八烷、正二十七烷、正二十六烷、正二十五烷、正二十四烷、正二十三烷、正二十二烷、正二十一烷、正二十烷、正十九烷、十八烷、正十七烷、正十六烷、正十五烷、正十四烷、正十三烷。相变材料可以替代地任选另外包括:结晶材料,如2,2-二甲基-1,3-丙二醇、2-羟甲基-2-甲基-1,3-丙二醇,直链或支链烃的酸如二十碳烷酸和酯如棕榈酸甲酯、脂肪醇和它们的混合物。
正如这里的实施例中所述,在香料的情况下,香精油优选用作有益剂和壁形成材料的溶剂。
通过所得聚合物的带电域或带电侧链基团化学粘附于微胶囊表面、特别是微胶囊外表面,本发明可以调节壳聚糖脲基微胶囊的表面电荷。
水相可以任选地包括乳化剂。乳化剂的非限定性实例包括:烷基硫酸酯、烷基醚硫酸酯、烷基异硫酸酯、烷基羧酸酯、烷基磺基琥珀酸酯、烷基琥珀酸酯、烷基硫酸酯盐(如十二烷基硫酸钠)、烷基肌氨酸酯、蛋白质水解物的烷基衍生物、酰基天冬氨酸酯、烷基或烷基醚或烷基芳基醚磷酸酯的水溶性盐,十二烷基硫酸钠、磷脂或卵磷脂,或皂、硬脂酸、油酸和棕榈酸的钠、钾或铵盐、烷基芳基磺酸盐如十二烷基苯磺酸钠、二烷基磺基琥珀酸钠、二辛基磺基琥珀酸钠、二月桂基磺基琥珀酸钠、聚(苯乙烯磺酸酯)钠盐、异丁烯-马来酸酐共聚物、***树胶、海藻酸钠、羧甲基纤维素、硫酸纤维素和果胶、聚(苯乙烯磺酸酯)、异丁烯-马来酸酐共聚物、卡拉胶、海藻酸钠、果胶酸、黄蓍胶、杏仁胶和琼脂;半合成聚合物,如羧甲基纤维素、硫酸化的纤维素、硫酸化的甲基纤维素、羧甲基淀粉、磷酸化的淀粉、木质素磺酸;以及合成聚合物,如马来酸酐共聚物(包括其水解物)、聚丙烯酸、聚甲基丙烯酸、丙烯酸-丙烯酸丁酯共聚物或巴豆酸的均聚物和共聚物、乙烯基苯磺酸或2-丙烯酰胺基-2-甲基丙烷磺酸的均聚物和共聚物,以及这些聚合物和共聚物的部分酰胺或部分酯,羧基改性的聚乙烯醇、磺酸改性的聚乙烯醇和磷酸改性的聚乙烯醇、磷酸化或硫酸化的三苯乙烯基苯酚乙氧基化物、棕榈酰胺丙基氯化三铵(Varisoft PATCTM,可由Degussa Evonik,Essen德国获得)、二硬脂基氯化二铵、十六烷基三甲基氯化铵、季铵化合物、脂肪胺、脂族卤化铵、烷基二甲基苯甲基卤化铵、烷基二甲基乙基卤化铵、聚乙烯亚胺、聚(2-二甲氨基)乙基甲基丙烯酸酯)甲基氯季盐,聚(l-乙烯基吡咯烷酮-共-2-二甲氨基乙基甲基丙烯酸酯)、聚(丙烯酰胺-共-二烯丙基二甲基氯化铵)、聚(烯丙胺)、聚[双(2-氯乙基)醚-间-1,3-双[3-(二甲氨基)丙基]脲]季铵化物、和聚(二甲基胺-共-环氧氯丙烷-共-乙二胺)、脂肪胺与环氧烷的缩合产物,具有长链脂族基团的季铵化合物,如二硬脂基氯化二铵和脂肪胺、烷基二甲基苯甲基卤化铵、烷基二甲基乙基卤化铵、聚亚烷基乙二醇醚、烷基酚、脂肪醇或脂肪酸与环氧烷、乙氧基化的烷基酚、乙氧基化的芳基酚、乙氧基化的聚芳基酚的缩合产物,利用多元醇增溶的羧酸酯、聚乙烯醇、聚乙酸乙烯醋、或聚乙烯醇-聚乙酸乙烯酯的共聚物、聚丙烯酰胺、聚(N-异丙基丙烯酰胺)、聚(2-羟基丙基甲基丙烯酸酯)、聚(-乙基-2-恶唑啉)、聚(2-异丙烯基-2-恶唑啉-共-甲基甲基丙烯酸酯)、聚(甲基乙烯基醚)和聚(乙烯醇-共-聚乙烯)和椰酰胺丙基甜菜碱。如果采用,以制剂的总重量为基准,乳化剂通常为约0.1-40wt%,优选约0.2-15wt%,更典型地为0.5-10wt%。
除了有益剂以外,微胶囊还可以包封分配调节剂。分配调节剂的非限定性实例包括肉豆蔻酸异丙酯、C4-C24脂肪酸的单酯、二酯和三酯、蓖麻油、矿物油、大豆油、十六烷酸、异十二烷甲酯、异石蜡油、聚二甲基硅氧烷、溴化植物油和它们的组合物。微胶囊可以具有不同的分配改性剂与有益剂的比,从而制备具有不同释放模式的不同微胶囊群。这些群也可以结合不同的香精油,从而使得微胶囊群展示不同的释放模式和不同的气味体验。US2011-0268802公开了分配微胶囊和调节剂的其它非限定性实例,其在这里作为参考引入。
在壳聚糖微胶囊的形成过程中,水溶液含有残余量的水解壳聚糖。这为微胶囊脱水提供了一种选择,如通过倾析、过滤、离心或其它分离技术脱水。替代地,可以喷雾干燥壳聚糖聚脲微胶囊的含水浆液,形成进一步由来自水相的残余水解壳聚糖层涂覆的壳聚糖聚脲微胶囊。
在一个实施方案中,可将形成的微胶囊浆液进一步分散在附加的水中或利用低浓度的残余外涂层水解壳聚糖,产生可在干燥时开裂的壳聚糖聚脲微胶囊,提供在一些用途中有用的附加释放机理,如香料递送或靶向递送的农用活性物质。
在方法和组合物的一些实例中,微胶囊可由一个或多个不同的群组成。组合物可具有至少两个不同的微胶囊群,这些群在香精油的确切组成以及中值粒径和/或分配改性剂与香精油的重量比(PM:PO)方面不同。在一些实例中,组合物包括两个以上的不同群,它们在香精油的确切组成和断裂强度方面不同。在另一些实例中,微胶囊群可以在分配调节剂与香精油的重量比方面不同。在一些实例中,组合物可以包括分配调节剂与第一香精油的第一重量比为2:3-3:2的第一微胶囊群和分配调节剂与第二香精油的第二重量比小于2:3但大于0的第二微胶囊群。
在一些实施方案中,每个不同的微胶囊群可在不同的浆液中制备。例如,第一微胶囊群可以包含在第一浆液中,和第二微胶囊群可包含在第二浆液中。应理解用于组合的不同浆液的数量没有限制,和配制者可以选择组合如3、10或15种不同的浆液。第一和第二微胶囊群可以在香精油的确切组成和中值粒径和/或PM:PO重量比方面不同。
在一些实施方案中,通过在容器中组合第一和第二浆液与至少一种辅助成分并任选包装起来可以制备所述组合物。在一些实例中,可以在不同的浆液中制备第一和第二微胶囊群,然后喷雾干燥形成颗粒。不同的浆液可以在喷雾干燥前组合、或者单独喷雾干燥和随后以颗粒粉末状态一起组合。一旦呈粉末状态,第一和第二微胶囊群就可以与辅助成分组合,形成可用作消费品、工业品、医疗品或其它商品的原料的组合物。在一些实例中,将至少一个微胶囊群喷雾干燥和与第二微胶囊群的浆液组合。在一些实例中,干燥至少一个微胶囊群,其通过喷雾干燥、流化床干燥、托盘干燥或其它可用的这类干燥方法制备。
在一些实例中,浆液或干颗粒可以包括一种或多种辅助材料,如选自如下的处理助剂:载体、聚集抑制材料、沉积助剂、颗粒悬浮聚合物和它们的混合物。聚集抑制材料的非限定性实例包括可在颗粒周围具有电荷屏蔽效应的盐,如氯化镁、氯化钙、溴化镁、硫酸镁和它们的混合物。颗粒悬浮聚合物的非限定性实例包括:聚合物如黄原胶、卡拉胶、瓜尔豆胶、虫胶、海藻酸钠、壳聚糖;纤维素材料,如羧甲基纤维素、羟基丙基甲基纤维素、带阳离子电荷的纤维素材料;聚丙烯酸;聚乙烯醇;氢化蓖麻油;二硬脂酸乙二醇酯;和它们的混合物。
在一些实施方案中,所述浆液可以包括一种或多种处理助剂,选自水、聚集抑制材料如二价盐、颗粒悬浮聚合物如黄原胶、瓜尔豆胶、羧甲基纤维素。
在本发明的其它实例中,所述浆液可以包括一种或多种选自如下的载体:极性溶剂,包括但不限于水、乙二醇、丙二醇、聚乙二醇、甘油;非极性溶剂,包括但不限于矿物油、香精原料、硅油、烃石蜡油和它们的混合物。
在一些实例中,所述浆液可包括沉积助剂,其可包括选自如下的聚合物:多糖,在一个方面有阳离子改性的淀粉和/或阳离子改性的瓜尔胶;聚硅氧烷;聚二烯丙基二甲基卤化铵;聚二烯丙基二甲基氯化铵与聚乙烯吡咯烷酮的共聚物;含聚乙二醇和聚乙烯吡咯烷酮的组合物;丙烯酰胺;咪唑类;咪唑啉卤化物;聚乙烯胺;聚乙烯胺与N-乙烯基甲酰胺的共聚物;聚乙烯甲酰胺;聚乙烯醇;与硼酸交联的聚乙烯醇;聚丙烯酸;聚甘油醚-有机硅交联聚合物;聚丙烯酸、聚丙烯酸酯、聚乙烯基胺与胺的聚乙烯醇低聚物的共聚物,在一个方面有二亚乙基三胺、乙二胺、双(3-氨基丙基)哌嗪、N,N-双-(3-氨基丙基)甲胺、三(2-氨基乙基)胺和它们的混合物;聚乙烯亚胺、衍生的聚乙烯亚胺,在一个方面有乙氧基化的聚乙烯亚胺;在聚丁二烯、聚异戊二烯、聚丁二烯/苯乙烯、聚丁二烯/丙烯腈、羧基终端的聚丁二烯/丙烯腈或它们的组合物的骨架上含有选自羧酸部分、胺部分、羟基部分和腈部分的至少两个部分的聚合化合物;阴离子表面活性剂与阳离子聚合物的预形成凝聚体;多胺和它们的混合物。
在描述本发明的一些附加实例中,至少一个微胶囊群可包含在聚集体中,然后与不同的微胶囊群和至少一种辅助材料组合。所述聚集体可以包括选自如下的材料:硅石、柠檬酸、碳酸钠、硫酸钠、氯化钠和粘合剂如硅酸钠、改性纤维素、聚乙二醇、聚丙烯酸酯、聚丙烯酸、沸石和它们的混合物.
在这里公开的方法中应用的合适设备可以包括连续搅拌釜反应器、均化器、涡轮搅拌器、循环泵、桨叶混合器、犁式剪切混合器、带式混合器、垂直轴造粒机和圆筒混合机,包括间歇和连续工艺配置(如果可用的话)、喷雾干燥器和挤出机。这种设备可以由LodigeGmbH(Paderborn,德国)、Littleford Day,Inc.(Florence,Ky.,美国)、Forberg AS(Larvik,挪威)、Glatt Ingenieurtechnik GmbH(Weimar,德国)、Niro(Soeborg,丹麦)、Hosokawa Bepex Corp.(Minneapolis,Minn.,美国)、Arde Barinco(New Jersey,美国)获得。确定降解%的程序
降解%按1992年7月17日采纳的“OECD Guideline for Testing of Chemicals”301B CO2 Evolution(Modified Sturm Test)测定。为了方便参考,该测试方法在这里称为测试方法OECD 301B。
确定游离油的程序
这种方法测量水相中的油量,和用作内部标准溶液1mg/ml邻苯二甲酸二丁酯(DBP)/己烷。
称取略多于250mg的DBP至小烧杯中并转移至250ml容量瓶中,彻底冲洗烧杯。注入己烷至250ml。
样品制备:称取约1.5-2克(40滴)胶囊浆液至20ml摇荡瓶中,加入10毫升ISTD溶液,盖紧瓶盖。在30分钟内剧烈摇晃几次,将溶液移到自动进样瓶中,通过GC进行分析。
其它细节。仪器:连接到HP Chem Station Software的HP5890GC;柱子:5m x0.32mm内径,含1μm DB-1液相;温度50℃1分钟,然后以15℃/min加热至320℃;注射器:275℃;检测器:325℃;注射2ul。
计算:加和总峰面积减去样品和标定物的DBP面积。
计算游离芯油mg:
样品的总面积x标定溶液中油mg=游离油mg
标定物的总面积
计算游离芯油%
游离芯油mgx100=湿浆液中游离芯油%
样品重量(mg)
确定有益剂泄漏的程序
获得2个1克有益剂颗粒组合物样品。将1克(样品1)颗粒组合物加入99克其中采用颗粒的产品基质中。在密封玻璃罐中在35℃下老化含颗粒的产品基质(样品1)2周。类似地老化另外1克样品(样品2)。
2周后,应用过滤由产品基质(样品1)和颗粒组合物(样品2)中回收颗粒组合物的颗粒。用溶剂处理每种颗粒样品,其会从每种样品颗粒中提取出所有有益剂。将每个样品的含有益剂的溶剂注入气相色谱,和积分峰面积以确定从每个样品中提取出的有益剂的总量。
通过计算从样品2提取的有益剂总量所得值与样品1的差,确定有益剂的泄漏百分比,按占从样本2提取的有益剂总量的百分比表示,如下式所示:
如图1所示,用壳聚糖制备的聚脲胶囊表现出正zeta电势。这种胶囊对织物有改进的沉积效率。
除非另有说明,否则所有百分比和比均按重量计。除非另有说明,所有百分比和比均以总组合物为基准计。
应理解本说明书中给出的每个最大数值限均包括每个较小数值限,就像这些较小数值限在这里明确写出了一样。本说明书中给出的每个最小数值限将包括每个较大数值限,就像这些较大数值限在这里明确写出了一样。本说明书中给出的每个数值范围将包括落在较宽数值范围内的每个较窄数值范围,就像较窄数值范围在这里明确写出了一样。
在如下实施例中,各缩写对应表1中所列材料。
表1
对比例1
通过在273.60g去离子水中混合86.40g 5%Selvol 540制备水相I。通过一起混合159.38g香精油和23.91g肉豆蔻酸异丙酯和然后在搅拌下向其中溶解4.0g Takenate D-110N制备油相。通过在25.00g水中混合0.38g二亚乙基三胺制备水相II。通过混合油相和水相I并研磨获得目标颗粒粒度而形成乳液。然后向所述乳液中加入水相II,之后在30分钟内加热至40℃并保持60分钟。然后将乳液加热至85℃,并在搅拌下在该温度下保持6小时。最终浆液的游离油为4.068%。
对比例2
通过在夹套反应器中混合的同时将20.66g ChitoClear分散入439.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为2.61。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将139.58g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下没有形成胶囊。
实施例3
通过在夹套反应器中混合的同时将12.40g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.7。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将87.50g香精油和22.50g肉豆蔻酸异丙酯以及15.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.090%的游离油和3.604%的一周泄漏量。
实施例4
通过在夹套反应器中混合的同时将12.40g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为5.0。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及15.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.088%的游离油和2.918%的一周泄漏量。
实施例5
通过在夹套反应器中混合的同时将12.40g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为5.5。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及15.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.043%的游离油和2.009%的一周泄漏量。
实施例6
通过在夹套反应器中混合的同时将12.40g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为6.1。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及15.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.111%的游离油和1.909%的一周泄漏量。
实施例7
通过在夹套反应器中混合的同时将12.40g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为6.0。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及15.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.076%的游离油和1.112%的一周泄漏量。
实施例8
通过在夹套反应器中混合的同时将26.45g ChitoClear分散入450.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为6.0。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.674%的游离油和41.930%的一周泄漏量。
实施例9
通过在夹套反应器中混合的同时将12.40g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为6.0。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.272%的游离油和13.222%的一周泄漏量。
实施例10
通过在夹套反应器中混合的同时将20.66g ChitoClear分散入439.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为6.0。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.304%的游离油和17.454%的一周泄漏量。
实施例11
通过在夹套反应器中混合的同时将20.66g ChitoClear分散入439.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为3.8。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊的一周泄漏量为28.204%。
实施例12
通过在夹套反应器中混合的同时将20.66g ChitoClear分散入439.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.2。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊的一周泄漏量为24.174%。
实施例13
通过在夹套反应器中混合的同时将20.66g ChitoClear分散入439.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.9。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后用盐酸将乳液的pH调节至2.97。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊的一周泄漏量为76.182%。
实施例14
通过在夹套反应器中混合的同时将20.66g ChitoClear分散入439.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.7。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将159.38g香精油和23.91g肉豆蔻酸异丙酯以及4.00gTakenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.225%的游离油和52.824%的一周泄漏量。
实施例15
通过在夹套反应器中混合的同时将5.70g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.7。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将120.00g香精油和30.00g肉豆蔻酸异丙酯以及3.78g Mondur MR混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有7.358%的游离油。
实施例16
通过在夹套反应器中混合的同时将5.70g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.0。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将150.00g SAS-305与3.78g Mondur MR混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.006%的游离油。
实施例17
通过在夹套反应器中混合的同时将5.70g ChitoClear分散入350.00g水中而制备水相。然后在搅拌下用浓HCl将水相的pH调节为4.3。然后在60分钟内将水相温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将水相温度降低至25℃。通过在室温下将150.00g SAS-150与3.78g Mondur MR混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。在该pH条件下形成的胶囊具有0.005%的游离油。
表2
实施例 | 水解pH | 7天降解% | 14天降解% | 21天降解% | 28天降解% |
10 | 6.0 | 2.22 | 5.75 | 8.88 | 11.07 |
11 | 3.8 | 29.3 | 57.54 | 68.48 | 73.28 |
12 | 4.2 | 24.64 | 52.58 | 62.38 | 67.65 |
13 | 4.9 | 28.54 | 52.95 | 61.43 | 64.26 |
14 | 4.7 | 21.51 | 44.54 | 54.95 | 60.04 |
实施例18–对比例
通过在218.88g去离子水混合69.12g 5%Selvol 540制备水相I。通过一起混合124.64g香精油和31.16g肉豆蔻酸异丙酯并在搅拌下向其中溶解3.40g Takenate D-110N制备油相。通过在25.00g水中混合0.32g二亚乙基三胺制备水相II。通过将油相混合入水相I并研磨获得目标体积中值颗粒粒度29.52um而形成乳液。然后向所述乳液中加入水相II,之后在30分钟内加热至40℃并保持60分钟。然后将乳液加热至85℃,并在搅拌下在该温度下保持6小时。然后在90分钟内将乳液冷却至25℃。所形成的胶囊具有0.366%的游离油和一周泄漏量为20.77。
实施例19
通过在夹套反应器中混合的同时将121.50g壳聚糖ChitoClear分散入2578.5g去离子水中而制备壳聚糖原溶液。然后在搅拌下用浓HCl将壳聚糖分散液的pH调节为5.28。然后在60分钟内将壳聚糖溶液的温度升高至85℃,随后在85℃下保持一段时间以水解ChitoClear。水解步骤后在90分钟内将温度降低至25℃。水解壳聚糖溶液的pH为5.36。通过在夹套反应器中混合362.36g上述壳聚糖原溶液而制备水相。通过在室温下将124.64g香精和31.16g肉豆蔻酸异丙酯以及3.40g Takenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。所形成的胶囊具有0.057%的游离油和一周泄漏量为9.19%。
实施例20
通过在夹套反应器中混合362.36g上述壳聚糖原溶液与3.66g Selvol 540溶液而制备水相。通过在室温下将124.64g香精和31.16g肉豆蔻酸异丙酯以及3.40g Takenate D-110N混合在一起制备油相。在高剪切研磨下将油相加入水相中获得乳液。在30分钟内将乳液加热至40℃并保持60分钟。然后在混合的同时将乳液加热至85℃并在该温度下保持6小时。所形成的胶囊具有0.065%的游离油和一周泄漏量为11.38%。
包含递送颗粒的液体织物柔软剂的性能评价
按表4所述制备含递送颗粒的液体织物柔软剂,以获得0.5%的香料当量。将配制物过夜平衡(~12小时)。如表3所列,9磅洗涤负荷中包括棉质和聚酯/棉混纺制品(毛巾、T恤、枕套和手巾)的混合物。应用无香味的洗涤剂实施洗涤循环,和在冲洗循环中以90克的剂量添加配制产品。
表3
洗涤负荷:9lb | 物品个数 | 织物 |
毛巾 | 10 | 100%棉 |
T恤(V-领),L | 12 | 100%棉 |
t-恤(圆领),L | 2 | 100%棉 |
枕套 | 10 | 60/40棉/聚酯混纺 |
手巾 | 10 | 86/14棉/聚酯混纺 |
一个10人小组在洗涤前后对物品进行了评估,按以下等级对感官强度进行评级:0=无气味,1=微弱气味,2=明显气味,3=非常强烈的气味。摩擦前后的感官强度如表4所示。
表4
A | B | C | D | |
液体织物软化剂的制备 | ||||
不含香料的DownyTM液体织物软化剂 | 88.163g | 88.140g | 88.282g | 89.550g |
香精 | 0.450g | |||
经对比例18的递送颗粒的香精 | 1.718g | |||
经实施例19的递送颗粒的香精 | 1.860g | |||
经实施例20的递送颗粒的香精 | 1.837g | |||
感观评价 | ||||
摩擦前的感观强度 | 1.30 | 0.60 | 0.50 | 0.50 |
摩擦后的感观强度 | 1.35 | 1.30 | 0.70 | 0.70 |
包含递送颗粒的洗衣液的性能评价
按下表5所述制备包含递送颗粒的洗衣液,以获得0.5%的香料当量。将配制物过夜平衡(~12小时)。如表3所列,9磅洗涤负荷中包括棉质和聚酯/棉混纺制品(毛巾、T恤、枕套和手巾)的混合物。在冲洗循环中以40克的剂量添加配制产品。
一个10人小组在洗涤前后对物品进行了评估,按以下等级对感官强度进行评级:0=无气味,1=微弱气味,2=明显气味,3=非常强烈的气味。摩擦前后的感官强度如表5所示。
表5
按OECD Guidelines for the Testing of Chemicals的测试方法OECD 301B测量降解百分比。在www.oecd-ilibrary.org.上可以获得其副本。
当按测试方法OECD TG 301B测试时,本发明组合物的壳在14天后降解至少40%、至少20天后降解至少50%和至少28天后降解至少60%。
除非在这里另外指出或在上下文中明确有相反表述,否则单数用语“a”和"an"的应用涵盖单数和复数。术语"包含"、"具有"、"包括"和"含有"应理解为开放式术语。在这里引用的所有参考文献,包括出版物、专利申请和专利,均作为参考引入。将某些实施方案描述为“优选的”实施方案以及将实施方案、特征或范围描述为优选或建议其为优选的,均不应认为是限制性的。本发明包括目前被认为不太优选的实施方案以及在本文中可能这样描述的实施方案。除非在这里另有说明或上下文中明确有相反表述,否则这里描述的所有方法均可以按任何合适的顺序实施。应用本文提供的任何及所有实例或示例性语言(如“例如”)均用于描述本发明,而不是对本发明的范围进行限制。这里有关本发明或优选实施方案的性质或好处的所有描述均不用于限制。本发明包括适用法律所允许的对这里描述主题的所有调整和等价内容。另外,除非在这里另有说明或在上下文中明确有相反表述,否则本发明包括上述元素所有可能变体的任何组合。这里对任何参考文献或专利的描述,即使被确认为"现有技术",也不是认可该文献或专利是针对本发明的可获得的现有技术。权利要求以外的用语均不限制本发明范围。除非在所附权利要求中有所反映,否则这里对构成本发明的某些特征的任何陈述或建议均不构成限制。
Claims (23)
1.一种形成微胶囊群的方法,所述微胶囊包括芯和包围所述芯的壳,所述方法包括:
通过在pH为3-6.5的含水酸性介质中在温度至少60℃下水解壳聚糖至少1小时形成水相;
形成油相,包括任选与添加的油一起溶解至少一种有益剂和至少一种多异氰酸酯;
通过在高剪切搅拌下使水相和油相混合入过量的水相形成乳液,从而形成在水相中分散的油相和有益剂的液滴;
通过加热至至少40℃足够时间固化乳液,从而在液滴与水相的界面处形成壳,所述壳包括多异氰酸酯和水解壳聚糖的反应产物,和所述壳包围含有油相和有益剂的液滴的芯。
2.一种形成微胶囊群的方法,所述微胶囊包括芯和包围所述芯的壳,所述方法包括:
通过在pH为3-6.5的含水酸性介质中在温度至少45℃下水解壳聚糖至少1小时形成水相;
形成油相,包括任选与添加的油一起溶解至少一种有益剂和至少一种多异氰酸酯;
通过在高剪切搅拌下使水相和油相混合入过量的水相形成乳液,从而形成在水相中分散的油相和有益剂的液滴;
通过加热至至少40℃足够时间固化乳液,从而在液滴与水相的界面处形成壳,所述壳包括多异氰酸酯和水解壳聚糖的反应产物,和所述壳包围含有油相和有益剂的液滴的芯。
3.权利要求1所述的方法,其中在水解步骤中所述壳聚糖脱乙酰化至至少75%。
4.权利要求1所述的方法,其中在水解步骤中所述壳聚糖解聚为95kDa或更低的平均大小。
5.权利要求1所述的方法,其中所形成的壳为壳聚糖聚脲,其壳聚糖含量基于所述壳的重量为至少21wt%。
6.权利要求1所述的方法,其中所述微胶囊群包含含水浆液,所述含水浆液在浆液中具有残余水解壳聚糖。
7.权利要求6所述的方法,其中喷雾干燥所述含水浆液形成微胶囊,所述微胶囊包覆有由浆液沉积到微胶囊上的残余水解壳聚糖层。
8.权利要求1所述的方法,其中水相中水解壳聚糖相对于油相中异氰酸酯的重量比为21:79至90:10。
9.权利要求1所述的方法,其中所述多异氰酸酯选自甲苯二异氰酸酯的多异氰脲酸酯、甲苯二异氰酸酯的三羟甲基丙烷加合物、亚二甲苯基二异氰酸酯的三羟甲基丙烷加合物、亚甲基二苯基异氰酸酯、甲苯二异氰酸酯、四甲基二甲苯胺二异氰酸酯、萘-1,5-二异氰酸酯和亚苯基二异氰酸酯。
10.权利要求1所述的方法,其中干燥所述微胶囊,且干燥后开裂,从而将所述芯释放出来。
11.一种组合物,其包含芯-壳微胶囊,所述芯包含有益剂,所述壳包括含多异氰酸酯与壳聚糖的反应产物的聚脲树脂,
其中所述壳聚糖首先在pH为3-6.5的酸性介质中在温度至少60℃下水解至少1小时;
其中所述壳的至少21wt%由衍生自水解壳聚糖的部分组成;
其中当按测试方法OECD 301B测试时所述壳在至少14天内降解至少40%。
12.权利要求11所述的组合物,其中所述微胶囊在干燥后开裂,释放出有益剂。
13.权利要求11所述的组合物,其中多异氰酸酯与水解壳聚糖的重量比为79:21至10:90。
14.权利要求11所述的组合物,所述壳占所述芯-壳微胶囊的1-15wt%。
15.权利要求11所述的组合物,其中所述多异氰酸酯选自甲苯二异氰酸酯的多异氰脲酸酯、甲苯二异氰酸酯的三羟甲基丙烷加合物、亚二甲苯基二异氰酸酯的三羟甲基丙烷加合物、亚甲基二苯基异氰酸酯、甲苯二异氰酸酯、四甲基二甲苯胺二异氰酸酯、萘-1,5-二异氰酸酯和亚苯基二异氰酸酯。
16.权利要求15所述的组合物,其中当按测试方法OECD 301B测试时所述壳在至少20天后降解至少50%。
17.权利要求11所述的组合物,其中所述壳聚糖的脱乙酰度为至少50%。
18.权利要求11所述的组合物,其中所述芯-壳微胶囊的芯壳重量比为至多99.5:0.5。
19.权利要求11所述的组合物,其中所述有益剂选自香精、香料、农用活性物质、相变材料、精油、润滑剂、着色剂、防腐剂、抗菌活性物质、抗真菌活性剂、除草剂、抗病毒活性剂、防腐活性剂、抗氧化剂、生物活性剂、除臭剂、润肤剂、保湿剂、去角质剂、紫外线吸收剂、腐蚀抑制剂、硅油、蜡、漂白颗粒、织物调理剂、恶臭减少剂、染料、荧光增白剂、止汗活性物质和它们的混合物。
20.权利要求11所述的组合物,其中所述芯-壳微胶囊具有1-100微米的平均粒度。
21.权利要求11所述的组合物,其中所述微胶囊为阳离子型的。
22.权利要求11所述的组合物,其中所述微胶囊在pH 4.5下的zeta电势为至少15mV。
23.权利要求15所述的组合物,其中当按测试方法OECD 301B测试时,所述壳在至少28天后降解其质量的至少60%。
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