CN103547614A - 含有有机改性的碳硅氧烷单体的组合物及其用途 - Google Patents
含有有机改性的碳硅氧烷单体的组合物及其用途 Download PDFInfo
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- CN103547614A CN103547614A CN201180071089.5A CN201180071089A CN103547614A CN 103547614 A CN103547614 A CN 103547614A CN 201180071089 A CN201180071089 A CN 201180071089A CN 103547614 A CN103547614 A CN 103547614A
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
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- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A61K8/8141—Compositions of homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
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- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
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- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
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Abstract
本发明提供包含碳硅氧烷连接基以改善耐水解性的新型单-丙烯酸酯官能化硅氧烷单体。本发明还提供使用这些单体制备的共聚物及其在多种应用中的用途。
Description
技术领域
本发明涉及包含新型单-丙烯酸酯官能化有机改性的碳硅氧烷单体的组合物，其与相应的常规硅氧烷单体相比在酸性、碱性和中性pH条件下显示改善的水解稳定性。更具体而言，本发明涉及改善的组合物，其包括在pH6.5、7.0和7.5处的水解稳定性。
背景技术
给出本申请所讨论的任何出版物或参考文献，以描述本发明的背景和提供有关其实施的其它细节。在此不应认为本发明人承认由于在先发明而没有权利领先于这些公开内容。
由于其吸水性和高的氧渗透性，基于硅氧烷的水凝胶用于健康护理、个人护理、农业、涂料、家庭护理等领域中的多种应用。然而，这些有机硅水凝胶在酸性或碱性pH条件下显示差的水解稳定性。该效应在硅氧烷链长太短时是突出的。具体而言，众所周知基于三硅氧烷的化合物在酸性或碱性pH条件下经历快速水解裂解。本发明披露了水解更稳定的并且可用于形成水解稳定的有机硅水凝胶共聚物的硅氧烷组合物，所述有机硅水凝胶共聚物可潜在地用于包括上述的那些应用在内的多种应用中。
卡波姆是用作制药和化妆品中的增稠、分散、混悬和乳化试剂的合成性高分子量丙烯酸聚合物的通用名。它们可以是丙烯酸的均聚物以及与甲基丙烯酸和其它丙烯酸酯的共聚物。
发明内容
本发明的目的是提供单-丙烯酸酯官能化有机改性的碳硅氧烷组合物，其包含具有以下通式(I)的有机硅单体：
(R1R2R3)Si-Y1-[Si(R4R5)(Y2)]a-Si(R6R7)-Z (I)
其中a是0至约100；Y1是取代或未取代的含有1至约10个碳原子的二价烷基连接基；Y2是取代或未取代的含有1至约10个碳原子的二价烷基连接基或者杂原子诸如氮、氧或硫；R1、R2、R3、R4、R5、R6和R7独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基、-Y2-Si(R8R9R10)和A，其中R8R9R10独立地选自含有1至约10个碳的一价脂肪族、脂环族和芳族烃基；A是一价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；
Z具有以下通式(II)，
-R11-B-X (II)
其中R11是直链或支化的具有0至约20个碳原子的二价烷基连接基；B是二价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；X是丙烯酰胺或具有以下通式(III)的可聚合基团，
其中R12、R13和R14是氢或者取代或未取代的具有1至约20个碳的饱和一价烃基团。
本发明的另一目的是提供有机硅组合物，其包含源于本文所述的单体的均聚物和共聚物。
本发明的另一目的是提供含卡波姆的组合物，其显示其卡波姆组分的高水平分散，可用于制备各种个人护理产品、化妆品等。采用常规的设备和标准制造实践，能有效可行地获得本发明组合物及由其制备的制剂。
本发明的另一实施方式涉及制备所述有机硅单体的方法，其包括使具有以下所示通式的含有机硅化合物与具有如以下(V)所示的通式的末端不饱和基团化学反应，
(R1R2R3)Si-Y1-[Si(R4R5)(Y2)]a-Si(R6R7)-H (IV)
其中a是0至100；Y1是取代或未取代的含有1至约10个碳原子的二价烷基连接基，Y2可以是与Y1相同的或者可以是杂原子诸如氮、氧或硫。R1至R7独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基。此外，R1-R7可以是-Y2-Si(R8R9R10)和A，其中R8至R10独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基。A可以是一价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃并任选地包含杂原子。它一旦制得，即与具有如以下(V)所示的通式的末端不饱和基团反应，
R15-B-M (V)
其中R15是具有约0至约20个碳原子的直链或支化不饱和烷基基团，B是二价部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；优选地，B包含官能团诸如醇、醚、酯、酰胺、胺、酸及其盐、氰基、硫代基团、氨基甲酸乙酯、脲、磺酸酯、磺酰胺、磷酸酯以及它们的组合。M可以是羟基或卤素或环氧基或羧基。
当Y2是氧原子时，反应产物称为碳硅氧烷。一旦制得官能化碳硅氧烷，它与具有通式(VI)的烷基丙烯酰化合物反应以产生所述有机硅单体。
其中G可以是卤素或者羟基或者具有1至10个碳原子的烷基氧基。R12至R14可选自氢或者具有1至约20个碳的取代或未取代的饱和一价烃基团。官能化碳硅氧烷与具有通式(VI)的烷基丙烯酰化合物的反应可在季胺碱或碱性离子交换树脂(IER)或者形成共沸物的溶剂或反应物的存在下进行。形成共沸物的溶剂可选自己烷、庚烷、甲苯等，反应物诸如在惰性反应条件下的甲基丙烯酸甲酯。
附图说明
图1图示了针对实施例1和对比实施例2中制备的单体获得的在85℃在不同pH条件下的水解稳定性数据：(A)pH6.5、(B)pH7.0和(C)pH7.5。
具体实施方式
根据本发明，提供了包含单-丙烯酸酯和甲基丙烯酸酯官能化碳硅氧烷单体的组合物，所述单-丙烯酸酯和甲基丙烯酸酯官能化碳硅氧烷单体是非庞大的(non-bulky)并且显示改善的耐水解性。与相应的常规硅氧烷单体相比，本发明的碳硅氧烷单体显示在酸性和碱性pH下改善的耐水解性。与相应的常规硅氧烷单体的组合物/膜相比，由这些单体制备的固化组合物显示更好的氧渗透性和表面可湿性和较低的模量。
本申请所用的“均聚物”是由相同的重复单体制成的聚合物，“共聚物”是包含至少两种结构不同的单体的聚合物。名称诸如(甲基)丙烯酸酯是指具有丙烯酸酯或甲基丙烯酸酯官能团的单体。
在本申请说明书和所附权利要求中使用的单数形式“一”、“一种”和“该”包括复数形式，并且提及的具体数值至少包括该具体值，除非上下文中另外清楚地指出。
范围可以在本申请中表示为从“约”或“大约”一具体值和/或至“约”或“大约”另一具体值。当表达这样的范围时，另一实施方式包括从所述一具体值和/或至所述另一具体值。类似地，当数值通过使用前缀“约”表达为近似值时，应理解为该具体值形成另一实施方式。
本申请所述的所有方法可按任何适宜的顺序进行，除非本文另外指出或者根据上下文另有明显的冲突。本文给出的使用任何和所有的实例或者示例性语言(例如"诸如")仅仅意在更好地阐明本发明，而不对本发明的范围施加限定，除非另有要求。说明书中的语言不应理解为指定任何非要求保护的要素作为本发明实施所必需的。
本申请使用“包含”、“包括”、“含有”、“其特征在于”以及它们的语法等价表达是包含性或开放性术语，不排除其它未描述的要素或方法步骤，但是还要理解包括更严格的术语“由…组成”和“基本上…由组成”。
包含本发明的(甲基)丙烯酸酯官能化有机硅单体/聚合物的组合物、由这些组合物制备的产品以及它们的制备将在下文中进一步进行描述。
在本发明中，披露的单体具有碳硅烷连接基-Si-(CH2)n-Si-，其使得可能制备具有水解稳定的(耐水解)单体和聚合物的组合物。具体而言，本发明涉及包含用作水解稳定的有机硅单体的直链单-丙烯酸酯官能化有机改性的碳硅氧烷化合物的组合物。本发明的单-丙烯酸酯官能化的碳硅氧烷单体具有式(I)中所示的通式结构：
(R1R2R3)Si-Y1-[Si(R4R5)(Y2)]a-Si(R6R7)-Z (I).
本发明的式(I)的一种优选变体是具有如下所示的通式的单-丙烯酸酯官能化的碳硅氧烷单体。
其中a是0至100；Y1是取代或未取代的含有1至约10个碳原子的二价烷基连接基，Y2可是与Y1相同的或者可以为杂原子诸如氮、氧或硫。R1至R7独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基。R1-R7也可独立地选自-Y2-Si(R8R9R10)和A，其中R8至R10独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基。A可以是一价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃并且任选地包含杂原子。优选地，A包含官能团诸如烷基、醇、醚、酯、酰胺、胺、酸及其盐、氰基、硫代基团、氨基甲酸乙酯、脲、磺酸酯、磺酰胺、磷酸酯以及它们的组合。
在上面结构中的Z可具有如下所示的通式(II)，
-R11-B-X (II)
其中R11是直链或支化的具有约0至约20个碳原子的二价烷基连接基。
在通式(II)中的B是二价部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；优选地，B包含官能团诸如醇、醚、酯、酰胺、胺、酸及其盐、氰基、硫代基团、氨基甲酸乙酯、脲、磺酸酯、磺酰胺、磷酸酯以及它们的组合。
具体而言，B的一些代表性官能团示于下文。
-O-(C2H4O)p-(C3H6O)q-(C4H8O)r-
聚醚
其中p和q独立地为0至约100；r是0至约50并且(p+q+r)大于0。
羟基环己基
羟基丙基
氨基甲酸乙酯
脲
脲和氨基甲酸乙酯
碳酸酯
氨基甲酸酯
X是具有通式(III)的可聚合基团
其中R12至R14可选自氢或者具有1至约20个碳的取代或未取代的饱和一价烃基团或者X是丙烯酰胺。
本发明还涉及包含通过本文提供的碳硅氧烷单体的反应产物形成的聚合物的组合物。这些聚合物可以是一种本发明单体的均聚物或者两种结构不同的本发明有机硅单体的共聚物、和/或一种或多种本发明有机硅单体与至少一种适于在有机硅水凝胶中使用的其它亲水不饱和有机单体的共聚物，所述其它亲水不饱和有机单体的优选的非限制性实例是N,N-二甲基丙烯酰胺、甲基丙烯酸2-羟基乙基酯(HEMA)、丙烯酸2-羟基乙基酯(HEA)、N-乙烯基吡咯烷酮和甲基丙烯酸。在所述共聚物中，本发明的有机硅单体与所述其它亲水不饱和有机单体的比例是约1:100至约100:1，优选约20:80至约90:10，更优选约30:70至约80:20。
本发明的不饱和有机单体和碳硅氧烷单体是相互可混溶的并且形成均质混合物。相容溶剂的使用不是必需的。本发明的碳硅氧烷单体也是水溶性或水可分散的。水溶性碳硅氧烷单体可以按各种比例与水混溶以产生均质溶液。水可分散性碳硅氧烷单体不完全溶解在水中。浊度、雾度、形成凝胶和类似的在含水混合物中的不均匀性的可见迹象表明是分散体而不是溶液。水可溶性和水可分散性二者均是本发明的碳硅氧烷单体的适宜特性。当碳硅氧烷单体包含甲基丙烯酸酯化乙氧基化聚醚链段时，在聚醚含量小于总分子量的约60重量%时观察到水可分散性，在聚醚链段大于约60重量%时观察到水可溶性。
在形成包含聚合物的组合物之前，聚合物通过如下方法形成：混合期望的单体，将所得的混合物聚合并通过已知的使用自由基或阳离子或阴离子引发剂的热技术固化和使用光引发剂的UV固化技术在交联剂的存在下形成透明薄膜。向反应混合物中加入以形成聚合物的单体可以是单体或者预聚物。“预聚物”是具有可聚合基团的中分子量反应中间体聚合物。因此，应理解术语"含有有机硅的单体"、"碳硅氧烷单体"和"亲水单体"包括预聚物。
本发明的结构(I)的碳硅氧烷单体的一种优选变体具有下式
其中B是如代表实例中所示的二价聚醚，p是0至约100，优选2至约15，更优选约8，q和r等于0；Y1是约1至约10个碳、优选1至约5个碳、更优选约2个碳的二价烷基-连接基团。Y2是二价杂原子和二价烷基基团的组合，X是可聚合的甲基丙烯酸酯基团，a是0至约100，更优选0至20并包括0和20，甚至更优选1。在单体通式结构(I)中的各R基团是一价烷基-连接基团，优选甲基基团。R1至R7也可选自-Y2-Si(R8R9R10)和A。
来自本发明的结构(I)的碳硅氧烷单体的另一优选变体具有下式
其中B是二价含有羟基的脂环族环；X是可聚合的甲基丙烯酸酯基团，a是0至约100，更优选0至约20并包括0和20，甚至更优选1。Y1是约1至约10个碳、优选1至约5个碳、更优选约2个碳的二价烷基-连接基团。Y2是二价杂原子和二价烷基基团的组合。在单体通式结构(I)中的各R基团是一价烷基-连接基团，优选甲基基团。R1至R7也可选自–Y2-Si(R8R9R10)和A。
来自本发明的结构(I)的碳硅氧烷单体的又一优选变体具有下式，
其中B是二价烷基基团；X是可聚合的甲基丙烯酸酯基团，a是0至约100，更优选0至约20并包括0和20，甚至更优选1。Y1是约1至约10个碳、优选1至约5个碳、更优选约2个碳的二价烷基-连接基团。Y2是二价杂原子和二价烷基基团的组合。在单体通式结构(I)中的各R基团是一价烷基-连接基团，优选甲基基团。R1至R7也可选自–Y2-Si(R8R9R10)和A。
本发明的另一实施方式涉及制备所述碳硅氧烷单体的方法，其包括使碳硅氧烷化合物与具有如下所示通式的SiH官能团进行化学反应，
(R1R2R3)Si-Y1-[Si(R4R5)(Y2)]a-Si(R6R7)-H (IV)
其中a是0至100；Y1是取代或未取代的含有1至约10个碳原子的二价烷基连接基，Y2可以是Y1或二价杂原子。R1至R7独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基。此外，R1-R7可以是–Y2-Si(R8R9R10)和A，其中R8至R10独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族烃基和具有1至约10个碳的卤代烃基。A可以是一价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃并且任选地包含杂原子。通式(IV)化合物一旦制得，即与具有如以下(V)所示的通式的末端不饱和化合物反应，
R15-B–M (V)
其中R15是具有约0至约20个碳原子的直链或支化不饱和烷基，B是二价部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；优选地，B包含官能团诸如醇、醚、酯、酰胺、胺、酸及其盐、氰基、硫代基团、氨基甲酸乙酯、脲、磺酸酯、磺酰胺、磷酸酯以及它们的组合。M可以是羟基或卤素或环氧基或羧基。
一旦制得官能化碳硅氧烷，它与具有通式(VI)的烷基丙烯酰化合物反应以产生所述有机硅单体。
其中G可以是卤素或者羟基或者具有1至10个碳原子的烷基氧基。R12至R14可选自氢或者具有1至约20个碳的取代或未取代的饱和一价烃基团。官能化碳硅氧烷与具有通式(VI)的烷基丙烯酰化合物的反应可在季胺碱或碱性离子交换树脂(IER)或者形成共沸物的溶剂或反应物的存在下进行。形成共沸物的溶剂可选自己烷、庚烷、甲苯等，反应物诸如在惰性反应条件下的甲基丙烯酸甲酯。
一旦如上所述制得单体和聚合物，它们就可与其它相同或不同的单体或聚合物混合以制备本发明组合物。发现这些组合物具有有利于在化妆品和医药业中使用的性质。下文提供了本发明组合物的不同用途的一些实例和讨论。
本发明组合物的用途：
I.健康护理：
由于其与常规的水凝胶相比具有改善的氧渗透性，有机硅水凝胶共聚物在健康护理业中对于多种应用诸如隐形眼镜、伤口处理和给药应用显得日益重要。在健康护理中的一个主要挑战是用于这些应用的材料应是尺寸和化学稳定的，不应在使用条件(诸如灭菌、在含有缓冲液的含水媒介物中存储等)下发生水解性降解和渗出降解产物。本发明的碳硅氧烷单体显示相对于常规的硅氧烷单体改善的水解稳定性，其能够制备具有改善的水解稳定性的有机硅水凝胶共聚物用于健康护理相关的应用，其具体细节示于下面的段落中。此外，其单-官能化可聚合基团(单-丙烯酸酯或单-甲基丙烯酸酯官能度)提供对制备具有依据终端应用而期望的模量的有机硅水凝胶共聚物更好的控制。
A.隐形眼镜：
本发明的单-官能化的碳硅氧烷单体用于隐形眼镜应用具有多种优点。例如，(1)在本发明的硅氧烷单体组合物中存在碳硅氧烷连接基-Si-(CH2)n-Si-可有助于制备具有改善的水解稳定性的软水凝胶隐形眼镜材料。这意味着制得的有机硅水凝胶隐形眼镜是水解稳定的并且当其经受例如在眼睛中或者在消毒溶液中或者灭菌期间的使用条件时其化学组成和物理尺寸不发生变化。本发明的隐形眼镜材料还是能复原的。当在本文中使用术语能复原的，其是指在透镜变形之后透镜将快速返回其原始形状。(2)含有亲水侧链的本发明的单体与水凝胶共聚单体在整个组合物范围内相容，而无需使用任何溶剂或相容剂。使用各种水凝胶共聚单体和其混合物制备的共聚物膜是透明的，吸水的并固有地具有可湿润表面。(3)而且，人角膜要求约2×10-6cm3/(s cm2atm.)的氧气通过隐形眼镜以获得更好的眼睛健康，如Hill和Fatt报道(American Journal of Optometry and Archives of the AmericanAcademy of Optometry,Vol.47,p.50,1970)。由本发明单体制备的有机硅-水凝胶隐形眼镜材料允许氧通过其的更好的透过性，以满足人角膜所需的氧气要求。(4)本发明的单体可用于制备具有期望的较低模量的水凝胶共聚物，以改善透镜佩戴者的舒适性。(5)隐形眼镜材料可用本发明的单体制备，其采用本领域已知的固化技术(例如热和光化学辐照固化方法)而无需使用溶剂或相容剂。
B.伤口处理器件：
需要具有高的水含量和氧渗透性的水凝胶来制备伤口处理器件(例如透皮贴剂、伤口愈合贴剂、创伤敷裹贴片等)。在创伤敷裹材料中存在的水有助于提供湿气环境，以获得更好的舒适性和无痛的伤口处理。氧气也在伤口愈合中发挥重要的作用，在创伤敷裹材料中缺乏氧气转运已经确定为影响伤口愈合过程的一种最常见问题(Bok Y.Lee"The Wound Management Manual",McGraw-Hill,New York,2005,p.44)。氧气经血红蛋白转运至伤口是伤口愈合的重要过程。然而，伤口中损伤的组织可作为血红蛋白的障碍物，导致在伤口处的局部氧不足。由于细胞消耗了大量氧气，受损的组织通常是缺氧的。白细胞消耗氧气以产生抗感染的氧化剂。此外，成纤维细胞和内皮细胞针对伤口愈合也要求氧气。因此，氧气转运至伤口外部的唯一方式来自于大气，这要求创伤敷裹材料具有优良的氧渗透性以更好地治愈伤口。具有亲水部分诸如聚醚或其它亲水部分的本发明单体能够提供不但水解稳定的而且还吸水并高度氧渗透的有机硅水凝胶，使得它们适用于各种伤口处理应用的创伤敷裹材料。本发明的亲水有机硅组合物还提供优异的湿气环境以获得更好的舒适性和无痛的伤口处理。本发明的有机硅组合物可用作各种活性成分的潜在的载体或器件和那些活性物质在不同条件(例如pH、压力、温度、化学反应等)下的受控释放。
C.生物活性物质的靶向和受控给药
给药容易性和大的吸收表面积使得胃肠(GI)道成为给药的最受欢迎的途径。目前，正在研究几种水凝胶作为位点特异性给药的潜在器件以实现有效治疗。例如，生物相容的水凝胶用作结肠特异性给药系统用于治疗胃溃疡病中幽门螺杆菌感染。这些生物相容的水凝胶设计为高度溶胀的，并且在结肠酶或者微生物菌群存在下降解，以提供结肠特异性给药。此外，在药物在小肠中释放之前，生物相容的水凝胶在胃的苛刻的酸性环境中保护胰岛素。本发明的亲水性有机硅组合物可用于制备生物相容的基于有机硅水凝胶的给药装置，以在胃肠道中局部地释放药物至特异性位点。本发明的亲水性有机硅组合物也可用于其它生物相容的给药应用诸如泪点塞(puncta plugs)、眼线圈(ophtha coils)、视网膜移植、透皮贴剂、伤口愈合贴剂、经皮离子电渗疗法等。
D.经皮给药：
本发明的有机硅组合物可用于经皮给药应用。向皮肤给药通常用于治疗皮肤病或者用于皮肤的消毒。近年来，给药的经皮途径已经得到研究。已经探究溶胀的软水凝胶用于长时期给药，并且这些水凝胶可无痛地从皮肤上容易地除去，改善了患者的舒适性。在该领域的研究目前集中于离子电渗和电穿孔。正在研究基于水凝胶的制剂用于使用经皮离子电渗疗法的电助给药以提高产品诸如激素和烟碱的渗入。
E.皮下给药：
本发明的有机硅组合物也可用于皮下给药应用。在水凝胶的各种可能的治疗应用中，最有价值的应用是可植入的治疗器件。水凝胶制剂具有高的含水量、与生物组织环境相似性，使得它们相对生物相容的，并被提议用作药物的皮下给药。例如，水凝胶可用于蛋白质和肽的给药。目前，可植入的水凝胶通向可生物降解系统的发展，这不需要载药的植入物的手术移除。
其它健康护理应用包括组织工程的支架，抗微生物器件，抗菌器件，抗污涂料和抗真菌器件。
II.农药(pesticide)-农业、园艺、草皮(Turf)、观赏性植物(Ornamental)
和林业(Forestry)：
许多农药应用要求将助剂加到喷雾混合物中以在叶面上提供润湿和铺展。助剂常常是表面活性剂，其可具有各种功能，例如增加喷雾液滴在难以润湿的叶面上的保持力，提高铺展以改善喷雾的覆盖率，或者提供除草剂进入植物表皮的渗透性。这些助剂或者以罐侧添加剂(tank-side additive)提供，或者用作农药制剂中的组分。农药的典型应用包括农业、园艺、草皮、观赏性植物、家庭和花园、兽医和林业应用。
本发明的有机硅组合物及其聚合物可在农药组合物中用作水解稳定的表面活性剂，以作为桶混制剂中的浓缩物或稀释物的形式存在，存在的量足以提供0.005%～2%的最终使用浓度。任选地，农药组合物可包括赋形剂、助表面活性剂、溶剂、控泡剂、沉积助剂、阻流剂(drift retardants)、生物制剂、微量营养素、肥料等。术语农药是指用于消灭害虫的任何化合物，例如杀鼠剂、杀虫剂(insecticide)、杀螨剂、杀真菌剂和除草剂。可使用的农药的说明性实例包括，但不限于，生长调节剂、光合作用抑制剂、颜料抑制剂、有丝分裂中断剂(mitotic disrupter)、脂质生物合成抑制剂(lipid biosynthesisinhibitors)、细胞壁抑制剂，和细胞膜破裂剂(cell membrane disrupter)。在本发明的组合物中使用的农药的量随着所用的农药的类型而变化。可与本发明的组合物一起使用的农药化合物更具体的实例是，但不限于，除草剂和生长调节剂，例如：苯氧乙酸、苯氧丙酸、苯氧丁酸、苯甲酸、三嗪和均三嗪、取代的脲、尿嘧啶、苯达松、异苯敌草、灭草定、苯敌草、达草止、杀草强、异恶草酮、氟草同(fluridone)、达草灭、二硝基苯胺、异乐灵、黄草消、胺消草、氨基丙氟灵(prodiamnine)、氟乐灵、草甘膦、磺酰脲、咪唑啉酮、烯草酮、氯甲草、噁唑禾草灵、精吡氟禾草灵、吡氟氯禾灵、禾草克(quizalofop)、烯禾定、敌草腈、异恶草胺、和联吡啶鎓(bipyridylium)化合物。
本发明中可使用的杀真菌组合物可包括，但不限于，aldimorph、克啉菌、吗菌灵、烯酰吗啉；氟硅唑、戊环唑、环唑醇、氧唑菌、呋菌唑、丙环唑、戊唑醇等；烯菌灵、托布津、苯菌灵、多菌灵、百菌清(chlorothialonil)、氯硝胺、肟菌酯(trifloxystrobin)、氟嘧菌酯(fluoxystrobin)、醚菌胺(dimoxystrobin)、腈嘧菌酯(azoxystrobin)、灭菌胺(furcaranil)、丙氯灵、磺菌胺、恶唑菌酮(famoxadone)、克菌丹、代森锰、代森锰锌、多敌菌、多果定，和甲霜灵。
能与本发明的组合物一起使用的杀虫剂、杀幼虫剂、杀螨剂和杀卵剂(ovacide)化合物包括，但不限于，苏云金杆菌、艾克敌105(spinosad)、齐墩螨素(abamectin)、多拉克汀(doramectin)、lepimectin、除虫菊酯、西维因、抗蚜威(pirimicarb)、涕灭威、灭多虫、虫螨脒、硼酸、杀虫脒、双苯氟脲(novaluron)、双三氟虫脲(bistrifluron)、杀虫隆、氟脲杀、咪蚜胺、二嗪农、乙酰甲胺磷、硫丹、克来范、乐果、乙基谷硫磷、谷硫磷、异恶唑磷(izoxathion)、毒死蜱、四螨嗪、氯氟氰菊酯、氯菊酯、氟氯菊酯、氯氰菊酯等。
肥料和微量营养素包括，但不限于，硫酸锌、硫酸亚铁、硫酸铵、脲、脲铵氮(urea ammonium nitrogen)、硫代硫酸铵、硫酸钾、磷酸一铵、磷酸脲、硝酸钙、硼酸、硼酸的钾盐和钠盐、磷酸、氢氧化镁、碳酸锰、多硫化钙、硫酸铜、硫酸锰、硫酸铁(iron sulfate)、硫酸钙、钼酸钠、氯化钙。
农药或肥料可为液体或固体。如果是固体，优选在施用之前它在溶剂或本发明的有机改性的硅氧烷中可溶，有机硅可用作溶剂，或者用于这种溶解性的表面活性剂，或者另外的表面活性剂可完成该功能。
III.涂料：
为了乳化、组分的增容、匀化(leveling)、流动和减少表面缺陷的目的，涂料制剂通常需要润湿剂或表面活性剂。此外，这些添加剂可给固化的或干的膜带来改进，例如改善的耐磨性、防粘连性、亲水性和疏水性。涂料制剂可作为抗污涂料、生物涂料、种子涂料、含溶剂的涂料、含水的涂料和粉末涂料存在。
涂料组分可用作：建筑涂料；OEM产品涂料例如汽车涂料和卷材涂料；专用涂料例如工业保养涂料(industrial maintenance coating)和船舶涂料；
典型的树脂类型包括：聚酯、醇酸树脂、丙烯酸类(acrylics)、环氧化合物以及它们的组合。
V.个人护理品：
本发明的有机改性的硅氧烷表面活性剂组合物可以以个人护理品乳液，例如露和霜的形式使用。如一般已知的，乳液包括至少两个不混溶相，其中一个是连续的，另一个是不连续的。另外的乳液可为具有变化的粘度的液体或固体。此外，乳液的粒度可使乳液是微乳液或迷你乳液，当粒度是足够小时，这些乳液可以是透明的。还可能制备乳液的乳液，它们通常被称为多重乳状液。这些乳液可为：1)水乳液，其中不连续相包括水，连续相包括本发明的有机改性的硅氧烷组合物；2)水乳液，其中不连续相包括本发明的有机改性的硅氧烷组合物，连续相包括水；3)非水乳液，其中不连续相包括非水羟基溶剂，连续相包括本发明的有机改性的硅氧烷组合物；和4)非水乳液，其中连续相包括非水羟基有机溶剂，不连续相包括本发明的有机改性的硅氧烷组合物。
本发明的单体可使用乳液聚合进行聚合，并且这些获得的单体与丙烯酸类共聚单体的共聚物形成优异的膜，其可用于各种皮肤护理和毛发护理应用(例如用于睫毛膏、定型胶、太阳光防护膜等)中。合适的个人护理品组合物通过以本领域已知的方式合并制得，例如，通过将一种或多种上述组分与所述的有机改性的硅氧烷组合物混合而制得。合适的个人护理品组合物可为单相的形式或乳液的形式，所述乳液形式包括其中有机硅相可为不连续相或连续相的水包油、油包水和无水乳液，以及多重乳状液，例如，油包水包油乳液和水包油包水乳液。
VI.家庭护理品：
本发明的有机改性的硅氧烷组合物及其聚合物可用作在家庭护理品应用中的表面活性剂，所述家庭护理品应用诸如衣物洗涤剂和织物柔软剂、餐具洗涤液、木材和家具上光剂、地板蜡、浴盆和瓷砖清洗剂、抽水马桶清洁剂、硬表面清洗剂、窗户清洁剂、防雾剂、排水沟清理剂、自动餐具洗涤剂和被单洗涤剂、地毯清洁剂、预洗剂指示剂(prewash spotter)、除锈剂和除垢剂。
合成实施例
以下实施例仅仅是示例说明，不应理解为限制本发明，其在所附权利要求中得到恰当描述。具有不同的官能团的单-甲基丙烯酸酯化碳硅氧烷单体如下制备。
单体制备
实施例1：
合成下式代表的化合物
该单体使用两步法制备。在第一步中，在羟基封端的甲代烯丙基聚醚与单-氢化物官能化碳硅氧烷之间发生氢化硅烷化反应。在第二步中，羟基基团通过甲基丙烯酸化反应转化为可聚合的甲基丙烯酸酯基团。单-氢化物官能化碳硅氧烷使用US7,259,220B1中所述的方法制备，US7,259,220B1以其整体通过引用并入本申请中。
在一种具体的方法中，将1-(2-三甲基甲硅烷基乙基)-1,1,3,3-四甲基二硅氧烷(25g)、氢化物官能化碳硅氧烷和甲代烯丙基-封端的聚乙二醇(46g,链中平均具有8个氧化乙烯(EO)单元)引入装备回流冷凝器、机械搅拌器、具有热电偶的温度控制器和氮气进气管的250mL三口圆底(RB)烧瓶中。将内容物在Karstedt催化剂(相对于全部反应物进料，50至100ppm的Pt)和缓冲液(US5,986,122)的存在下加热至80℃至90℃以避免例如脱氢偶合反应等副反应发生。在完成氢化硅烷化之后，从反应产物中减压除去挥发性化合物。以定量产率得到最终的产物，羟基封端的碳硅氧烷聚醚，其为无色透明液体，没有任何不期望的副产物。所得的纯净产物通过多核NMR谱进行很好的表征。本发明的有机硅聚醚的合成可使用或者不使用溶剂进行。若使用溶剂，则优选的溶剂包括甲苯、异丙醇或者甲乙酮。
H-NMR(ppm)：0.02(Si(CH3),0.3&0.6(SiCH2CH),0.4(SiCH2CH2Si),1.0(Si(CH3),1.9(-CH<),3.2&3.3(>CH-CH2-O-),3.6(-CH2CH2O-)。
Si-NMR(ppm)：3.4(Si(CH3)3CH2),7.2(O-Si(CH3)2(CH2)),8.5(O-Si(CH3)2(CH2CH2)。
然后，将上面步骤中合成的碳硅氧烷聚醚、三乙基胺(11.3g)和甲乙酮(100ml)引入装备滴液漏斗和搅拌桨的1升的三口圆底烧瓶中。将该烧瓶浸入冰浴中，在持续搅拌下使用滴液漏斗滴加甲基丙烯酰氯(11.2g)，历时约1小时。滴加完成之后，在室温继续搅拌另外的3小时。滤出在反应期间析出的三乙基胺盐酸盐。用旋转真空蒸发仪除去溶剂，得到最终的单体，其为无色至浅黄色透明液体。所采用的低沸点溶剂使得溶剂能在真空(即，小于约10mm Hg)下在约30℃至40℃的温度完全除去。所得的单体通过红外光谱、多核NMR谱得到很好的表征。
H-NMR(ppm)：0.02(Si(CH3),0.3&0.6(SiCH2CH),0.4(SiCH2CH2Si),0.98(Si(CH3),1.98(CH3),3.1&3.3(>CH-CH2-O-),3.64(-CH2CH2O-),4.2(CH2COO),5.6&6.15(CH2=)。
Si-NMR(ppm)：3.5(Si(CH3)3CH2),7.2(O-Si(CH3)2(CH2)),8.4(O-Si(CH3)2(CH2CH2)。
实施例2：
合成下式代表的化合物
该单体也使用两步法制备。在第一步中，在氢化物官能化碳硅氧烷与乙烯基官能化环己烯环氧化物之间发生氢化硅烷化反应。在第二步中，环氧基团与不饱和酸反应以在其中引入可聚合基团。
在一种具体的方法中，将1-(2-三甲基甲硅烷基乙基)-1,1,3,3-四甲基二硅氧烷(25g)和乙烯基环己烯环氧化物(13.2g)引入装备回流冷凝器、机械搅拌器、具有热电偶的温度控制器和氮气进气管的250mL三口圆底(RB)烧瓶中。将内容物在Karstedt催化剂(相对于全部反应物进料，10至50ppm的Pt)和缓冲液(US5,986,122)的存在下加热至80℃至90℃以避免例如脱氢偶合反应等副反应发生。在完成氢化硅烷化之后，通过减压蒸出不需要的挥发性化合物提纯反应产物。以定量产率得到最终的产物环氧官能化碳硅氧烷，其为无色透明液体，没有任何不期望的副产物。所得的纯净产物通过质子NMR谱进行很好的表征。本发明的环氧官能化碳硅氧烷的合成可使用或者不使用溶剂进行。若使用溶剂，则优选的溶剂包括甲苯、异丙醇或者甲乙酮。
H-NMR(ppm)：0.02(Si(CH3),0.4(SiCH2CH2Si),0.5(SiCH2),1.2-2(CH2)。
然后，将上面步骤中合成的环氧官能化碳硅氧烷、异丙醇钛(0.4wt%，相对于碳硅氧烷)和氢醌(0.0025wt%，相对于碳硅氧烷)引入装备滴液漏斗和搅拌桨的1升的三口圆底烧瓶中。将该烧瓶在油浴中加热至90℃，然后在持续搅拌下向该烧瓶中滴加丙烯酸(7.68g)。滴加完成之后，在90℃继续搅拌另外的5小时。溶剂(甲苯)和其它挥发性杂质使用旋转真空蒸发仪除去，得到最终的单体，其为无色透明液体。所得的单-丙烯酸酯化碳硅氧烷单体通过红外光谱、质子NMR谱得到很好的表征。
H-NMR(ppm):0.02(Si(CH3),0.4(SiCH2CH2Si),0.5(SiCH2),1.2-2(CH2),3.8&4.8(CH2),5.8,6.2&6.4(CH2=CH-)。
实施例3
形成有机硅-水凝胶膜
将实施例1中制得的化合物(49重量份)、甲基丙烯酸2-羟基乙基酯(49重量份)、乙二醇二甲基丙烯酸酯(EGDMA)(1重量份)和过氧化苯甲酰(1重量份)进行混合和搅拌。所得的澄清、均匀、透明的反应混合物用氮气进行净化，然后倒入不锈钢模具中。反应混合物的薄膜使用热空气烘箱在85℃热固化8小时。由此制得的有机硅水凝胶膜是透明和吸水的。
实施例4
以与实施例3中相同的方式制备有机硅-水凝胶膜，不同之处是使用实施例2中制得的化合物代替实施例1中制得的化合物。由此制得的有机硅水凝胶膜是透明和吸水的。
对比实施例1(CEx.1)
以与实施例1相同的方式制备单体，不同之处是使用1,1,1,3,5,5,5-七甲基三硅氧烷代替1-(2-三甲基甲硅烷基乙基)-1,1,3,3-四甲基二硅氧烷。制得的单-丙烯酸酯化硅氧烷单体通过红外光谱、多核NMR谱得到很好的表征。
H-NMR(ppm):0.02(Si(CH3),0.3&0.6(SiCH2CH),0.98(Si(CH3),1.98(CH3),3.1&3.3(>CH-CH2-O-),3.64(-CH2CH2O-),4.3(CH2COO),5.6&6.15(CH2=)。
Si-NMR(ppm):8(-Si(CH3)3),-22(O-Si(CH3)2-)。
本发明单体的水解稳定性通过使用HPLC进行测量(US专利申请公开20100069279)。将0.5wt%的实施例1(Ex.1)中制得的单体引入3个含有6.5、7和7.5pH溶液的不同小瓶中。将这些小瓶用防漏密封条进行密封，并加热至85℃。使用HPLC进行监控随时间变化的热加速的水解降解组成变化。与常规的硅氧烷单体(CEx.1)在酸性、中性和碱性pH条件下相比，本发明的单体(Ex.1)显示在酸性、碱性和中性条件下改善的水解稳定性(图1)。
图1显示在Ex.1和CEx.2中制得的单体在85℃在不同pH条件下的水解稳定性数据；(A)pH6.5、(B)pH7.0和(C)pH7.5。从图1中的曲线图可看出，与常规的硅氧烷单体(CEx.2)在酸性、中性和碱性pH条件下相比本发明的单体(Ex.1)显示在酸性、碱性和中性条件下改善的水解稳定性(图1)。
尽管参照优选实施方式描述了本发明，但是本领域技术人员应理解，可进行各种改变和用等同物代替其元素，而不脱离本发明范围。意图是，本发明不限于作为实施本发明的最佳方式披露的具体实施方式，本发明包括落在所附权利要求范围内的所有实施方式。将本申请提及的所有引用通过引用的方式清楚地并入本文。
Claims (26)
1.有机硅组合物，其包含至少一种具有通式(I)的碳硅氧烷连接基团：
(R1R2R3)Si-Y1-[Si(R4R5)(Y2)]a-Si(R6R7)-Z (I)
其中a是0至约100；
Y1是取代或未取代的含有1至约10个碳原子的二价烷基连接基；
Y2是取代或未取代的含有1至约10个碳原子的二价烷基连接基或者杂原子；
R1、R2、R3、R4、R5、R6和R7独立地选自含有1至约10个碳的一价脂肪族、脂环族或芳族或者卤代烃基，-Y2-Si(R8R9R10)和/或A，其中R8R9R10独立地选自含有1至约10个碳的一价脂肪族、脂环族和芳族烃基；A是一价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；
Z具有以下通式(II)
-R11-B-X (II)
其中R11是具有0至约20个碳原子的直链或支化二价烷基连接基，B是二价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃，X是丙烯酰胺或者选自以下的可聚合基团：取代或未取代的不饱和脂肪族或芳族烃、丙烯酸酯和甲基丙烯酸酯。
2.权利要求1的有机硅组合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13和R14独立地包括1至约9个碳原子的饱和一价烃基，氟代烃，芳烷基或芳基烷基，或者硅氧烷基。
3.权利要求1的有机硅组合物，其中A和B包含至少一种选自下组的官能团：烷基、醇基团、醚基团、酯基团、酰胺基团、胺基团、酸及其盐基团、氰基基团、硫代基团、氨基甲酸乙酯基团、脲基团、碳酸酯基团、氨基甲酸酯基团、磺酸酯基团、磺酰胺基团和磷酸酯基团。
4.权利要求1的有机硅组合物，其中B是以下二价部分中的一种：
-O-(C2H4O)p-(C3H6O)q-(C4H8O)r-
聚醚
其中p和q独立地为0至约100；r是0至约50，(p+q+r)大于0；
羟基化环己基，
羟基化丙基，
氨基甲酸乙酯，
脲，
脲和氨基甲酸乙酯，
碳酸酯，或者
氨基甲酸酯。
5.权利要求1的有机硅组合物，其中X是具有通式(III)的可聚合部分：
其中R12、R13和R14是氢或者具有1至约20个碳的取代或未取代的饱和一价烃或者卤代烃基。
6.权利要求1的水溶性和水可分散性碳硅氧烷组合物，其包含亲水聚乙二醇并具有以下所示通式：
其中p大于5。
7.权利要求1的碳硅氧烷组合物，具有下式
8.权利要求1的有机硅组合物，其中R1-R14中的一个包括氟代烃。
9.权利要求1的有机硅组合物，其中R1-R14各自独立地包含至少一个选自以下的部分：具有1至约9个碳原子的饱和一价脂肪族或芳族烃、和硅氧烷基。
10.权利要求1的有机硅组合物，其中A和B包含至少一种选自下组的官能团：醇基团、醚基团、酯基团、酰胺基团、胺基团、酸及其盐基团、氰基、硫代基团、氨基甲酸乙酯基团、脲基团、碳酸酯基团、氨基甲酸酯基团、磺酸酯基团、磺酰胺基团和磷酸酯基团。
11.包含权利要求1的有机硅组合物的健康护理组合物，其中该健康护理组合物包含生物活性物质，抗痤疮剂，抗老化剂，抗龋剂，抗真菌剂，抗微生物剂，抗氧化剂，抗肿瘤剂，抗病毒剂，抗炎剂，抗凝血剂，止血剂，皮肤角质层剥离剂，激素，酶，医药化合物，生物杀灭剂，外用止痛剂，口腔护理剂，口腔护理药物，氧化剂，还原剂，皮肤保护剂，香精油，驱虫剂，紫外线吸收剂，日光过滤剂，颜料，保湿剂，维生素以及它们的组合物。
12.权利要求11的包含权利要求1的有机硅组合物的健康护理组合物，其可用于包括以下的健康护理应用：水凝胶，给药系统，透皮贴剂，伤口愈合贴剂，创伤敷裹贴片，泪点塞，眼线圈，视网膜移植，透皮离子导入，组织工程的支架，抗微生物器件，抗菌器件，生物膜耐磨涂层，抗真菌器件，伤口处理器件，眼科器件，生物嵌入物，假肢和体内植入物。
13.包含权利要求1的有机硅组合物的个人护理组合物，其中个人护理成分包括：表面活性剂、乳化剂、溶剂、润肤剂、润湿剂、保湿剂、颜料、着色剂、香料、生物杀灭剂、防腐剂、螯合剂、抗氧化剂、抗微生物剂、抗真菌剂、止汗剂、皮肤角质层剥离剂、激素、酶、医药化合物、维生素、α-羟基酸、β-羟基酸、视黄醇、烟酰胺、亮肤剂、盐、电解质、醇、多元醇、紫外线吸收剂、植物性提取物、有机油、蜡、增稠剂、粒子填料、有机硅、粘土、增塑剂、吸留剂、感觉增强剂、酯、树脂、成膜剂、膜形成乳化剂、高折射率材料及其组合。
14.权利要求13的包含权利要求1的有机硅组合物的个人护理组合物，其可用于包括以下的个人护理应用：止汗剂/除臭剂，包括喷雾、棒和滚珠产品；剃须产品、皮肤洗剂、润湿剂、调色剂、沐浴产品、清洁产品、香波、调理剂、组合的香波/调理剂、摩丝、定型发胶、喷发胶、染发剂、染发产品、毛发漂白剂、卷发产品、直发剂、指甲抛光剂、指甲抛光剂去除剂、润甲霜和润甲水、角质层软化剂、防晒剂、驱虫剂、抗老化产品、口红、粉底、化妆底粉、眼线膏、眼影、胭脂、美容品、睫毛油、保湿制品、粉底、身体和手部制品、护肤制品、面部和颈部制品、强壮剂、化妆品、毛发修饰剂、气溶胶固定剂、芳香制品、剃须后用品、化妆制品、柔焦应用、夜用和日用护肤制品、非着色毛发制品、晒黑制品、合成和非合成皂条、洗手液、鼻贴、用于个人护理的非织造布应用、婴儿洗剂、婴儿沐浴液和香波、婴儿调理剂、剃须制品、黄瓜片、皮肤垫、化妆品去除剂、面部清洁产品、冷霜、防晒剂产品、摩丝、喷洒剂、膏状面膜和泥浆、面膜、古龙水和花露水、毛发护膜层、沐浴凝胶、面部和身体洗剂、个人护理冲洗产品、凝胶、泡沫浴用品、擦洗清洁剂、收敛剂、指甲调理剂、眼影条、用于面部或眼部的粉、唇部香脂、透明高光亮唇膏、毛发护理泵吸喷雾剂和其它非气溶胶喷雾剂、毛发卷曲控制凝胶、毛发免洗调理剂、发脂、毛发脱缠结产品、毛发固定剂、毛发漂白产品、皮肤洗剂、剃须前用品和电动剃须前用品、无水乳膏和洗剂、油/水乳液、水/油乳液、多重乳液和粗乳液和微乳液、防水乳膏和洗剂、抗痤疮制品、漱口剂、按摩油、牙膏、透明凝胶和棒、软膏基质、局部创伤愈合产品、气溶胶滑石粉、防护喷雾剂、维生素和抗老化制品、草本植物提取物制品、浴盐、沐浴和爽身乳液、毛发定型助剂、毛发、眼部、指甲和皮肤软固体施用品、受控释放个人护理品、毛发调理喷雾剂、皮肤护理润湿喷雾剂、皮肤擦拭剂、毛孔皮肤擦拭剂、毛孔清洁剂、瑕疵减少剂、皮肤角质层剥离剂、皮肤脱屑增强剂、皮肤用湿巾和布、脱毛制品、个人护理润滑剂、指甲着色制品、防晒剂、美容剂、毛发护理产品、皮肤护理产品、牙膏、用于施用至皮肤的医疗组合物的局部施用的药物递送系统和包含前述应用中的至少一种的组合。
15.包含权利要求1的有机硅组合物的农药制剂。
16.包含权利要求1的有机硅组合物的肥料制剂。
17.包含权利要求1的有机硅组合物的肥料涂料、种子涂料、抗污涂料、含水的涂料制剂。
18.制备权利要求1的有机硅组合物的的方法，包括使具有通式(IV)的含有机硅化合物与具有通式(V)的末端不饱和基团反应，产生官能化的碳硅氧烷，
(R1R2R3)Si-Y1-[Si(R4R5)(Y2)]a-Si(R6R7)-H (IV)
其中a是0至100；
Y1是取代或未取代的含有1至约10个碳原子的二价烷基连接基；
Y2是取代或未取代的含有1至约10个碳原子的二价烷基连接基或者二价杂原子；
R1、R2、R3、R4、R5、R6和R7独立地选自具有1至约10个碳的一价脂肪族、脂环族或芳族或卤代烃基，-Y2-Si(R8R9R10)和A，其中R8R9R10独立地选自含有1至约10个碳的一价脂肪族、脂环族和芳族烃基；A是一价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳环族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃；
R15-B-M (V)
其中R15选自具有0至约20个碳原子的直链或支化不饱和烷基，B是二价亲水或疏水部分，其选自取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃和含有杂原子的取代或未取代的、饱和和未饱和的脂肪族、脂环族或芳族烃，
A和B包括包含选自下组的官能团：烷基、醇基团、醚基团、酯基团、酰胺基团、胺基团、酸及其盐基团、氰基、硫代基团、氨基甲酸乙酯基团、脲基团、碳酸酯基团、氨基甲酸酯基团、磺酸酯基团、磺酰胺基团、磷酸酯基团和它们的组合；
M选自羟基、卤素、环氧和羧基；以及
使该官能化碳硅氧烷与具有下式(VI)的烷基丙烯酰化合物反应，产生具有权利要求1的通式(I)的所述有机硅单体：
其中G选自卤素、羟基和具有1至10个碳原子的烷基氧基，R12、R13和R14独立地选自氢、取代的具有1至约20个碳的饱和一价烃和未取代的具有1至约20个碳的饱和一价烃。
19.权利要求18的方法，其中所述官能化碳硅氧烷与所述烷基丙烯酰化合物的所述反应在至少一种叔碱或至少一种离子交换树脂(IER)和低沸点极性溶剂存在下进行。权利要求18的方法，其中发生反应的碳硅氧烷的存在量为总组合物的约5至约90重量%，烷基丙烯酰的存在量为总组合物的约5至约80重量%。
20.包含由权利要求18的方法制备的有机硅组合物的健康护理组合物，其中健康护理制剂包含生物活性物质，抗痤疮剂，抗老化剂，抗龋剂，抗真菌剂，抗微生物剂，抗氧化剂，抗肿瘤剂，抗病毒剂，抗炎剂，抗凝血剂，止血剂，皮肤角质层剥离剂，激素，酶，医药化合物，生物杀灭剂，外用止痛剂，口腔护理剂，口腔护理药物，氧化剂，还原剂，皮肤保护剂，香精油，驱虫剂，紫外线吸收剂，日光过滤剂，颜料，保湿剂，维生素以及它们的组合物。
21.权利要求20的包含由权利要求18的方法制备的有机硅组合物的健康护理组合物，其可用于包括以下的健康护理应用：水凝胶，给药系统，透皮贴剂，伤口愈合贴剂，创伤敷裹贴片，泪点塞，眼线圈，视网膜移植，透皮离子导入，组织工程的支架，抗微生物器件，抗菌器件，生物膜耐磨涂层，抗真菌器件，伤口处理器件，眼科器件，生物嵌入物，假肢和体内植入物。
22.包含由权利要求18的方法制备的有机硅组合物的个人护理组合物，其中个人护理成分包括：表面活性剂、乳化剂、溶剂、润肤剂、润湿剂、保湿剂、颜料、着色剂、香料、生物杀灭剂、防腐剂、螯合剂、抗氧化剂、抗微生物剂、抗真菌剂、止汗剂、皮肤角质层剥离剂、激素、酶、医药化合物、维生素、α-羟基酸、β-羟基酸、视黄醇、烟酰胺、亮肤剂、盐、电解质、醇、多元醇、紫外线吸收剂、植物性提取物、有机油、蜡、增稠剂、粒子填料、有机硅、粘土、增塑剂、吸留剂、感觉增强剂、酯、树脂、成膜剂、膜形成乳化剂、高折射率材料及其组合。
23.权利要求22的包含由权利要求18的方法制备的有机硅组合物的个人护理组合物，其可用于包括以下的个人护理应用：止汗剂/除臭剂，包括喷雾、棒和滚珠产品；剃须产品、皮肤洗剂、润湿剂、调色剂、沐浴产品、清洁产品、香波、调理剂、组合的香波/调理剂、摩丝、定型发胶、喷发胶、染发剂、染发产品、毛发漂白剂、卷发产品、直发剂、指甲抛光剂、指甲抛光剂去除剂、润甲霜和润甲水、角质层软化剂、防晒剂、驱虫剂、抗老化产品、口红、粉底、化妆底粉、眼线膏、眼影、胭脂、美容品、睫毛油、保湿制品、粉底、身体和手部制品、护肤制品、面部和颈部制品、强壮剂、化妆品、毛发修饰剂、气溶胶固定剂、芳香制品、剃须后用品、化妆制品、柔焦应用、夜用和日用护肤制品、非着色毛发制品、晒黑制品、合成和非合成皂条、洗手液、鼻贴、用于个人护理的非织造布应用、婴儿洗剂、婴儿沐浴液和香波、婴儿调理剂、剃须制品、黄瓜片、皮肤垫、化妆品去除剂、面部清洁产品、冷霜、防晒剂产品、摩丝、喷洒剂、膏状面膜和泥浆、面膜、古龙水和花露水、毛发护膜层、沐浴凝胶、面部和身体洗剂、个人护理冲洗产品、凝胶、泡沫浴用品、擦洗清洁剂、收敛剂、指甲调理剂、眼影条、用于面部或眼部的粉、唇部香脂、透明高光亮唇膏、毛发护理泵吸喷雾剂和其它非气溶胶喷雾剂、毛发卷曲控制凝胶、毛发免洗调理剂、发脂、毛发脱缠结产品、毛发固定剂、毛发漂白产品、皮肤洗剂、剃须前用品和电动剃须前用品、无水乳膏和洗剂、油/水乳液、水/油乳液、多重乳液和粗乳液和微乳液、防水乳膏和洗剂、抗痤疮制品、漱口剂、按摩油、牙膏、透明凝胶和棒、软膏基质、局部创伤愈合产品、气溶胶滑石粉、防护喷雾剂、维生素和抗老化制品、草本植物提取物制品、浴盐、沐浴和爽身乳液、毛发定型助剂、毛发、眼部、指甲和皮肤软固体施用品、受控释放个人护理品、毛发调理喷雾剂、皮肤护理润湿喷雾剂、皮肤擦拭剂、毛孔皮肤擦拭剂、毛孔清洁剂、瑕疵减少剂、皮肤角质层剥离剂、皮肤脱屑增强剂、皮肤用湿巾和布、脱毛制品、个人护理润滑剂、指甲着色制品、防晒剂、美容剂、毛发护理产品、皮肤护理产品、牙膏、用于施用至皮肤的医疗组合物的局部施用的药物递送系统和包含前述应用中的至少一种的组合。
24.包含由权利要求18的方法制备的有机硅组合物的农药制剂。
25.包含由权利要求18的方法制备的有机硅组合物的肥料制剂。
26.包含由权利要求18的方法制备的有机硅组合物的肥料涂料、种子涂料、抗污涂料、含水的涂料制剂。
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- 2011-03-21 KR KR1020137027384A patent/KR20130139347A/ko active IP Right Grant
- 2011-03-21 WO PCT/US2011/029164 patent/WO2012128751A1/en unknown
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- 2011-03-21 EP EP11713113.6A patent/EP2688938B1/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104288064A (zh) * | 2014-07-31 | 2015-01-21 | 广州市洁宝日用品有限公司 | 一种丝滑保湿水润面膜及其制备方法 |
| CN109068634A (zh) * | 2016-03-31 | 2018-12-21 | 莫门蒂夫性能材料股份有限公司 | 包含有机硅润湿剂的基于卵磷脂的喷雾佐剂 |
| CN106177874A (zh) * | 2016-08-30 | 2016-12-07 | 郑州市久久不忘生物技术有限公司 | 一种治疗咳喘的药物贴片及其制备方法 |
| CN110431195A (zh) * | 2017-01-19 | 2019-11-08 | 佐敦有限公司 | 防污组合物 |
| CN110431195B (zh) * | 2017-01-19 | 2022-02-08 | 佐敦有限公司 | 防污组合物 |
| CN108546336A (zh) * | 2018-04-25 | 2018-09-18 | 上海交通大学 | 一种利用转氨基作用制备可再加工交联弹性体的方法 |
| CN108546336B (zh) * | 2018-04-25 | 2020-11-10 | 上海交通大学 | 一种利用转氨基作用制备可再加工交联弹性体的方法 |
| CN109294242A (zh) * | 2018-08-23 | 2019-02-01 | 湖南博隽生物医药有限公司 | 一种婴幼儿雾化吸入器用材料及其制备方法 |
| CN109294242B (zh) * | 2018-08-23 | 2021-05-04 | 润生药业有限公司 | 一种婴幼儿雾化吸入器用材料及其制备方法 |
| CN109894990A (zh) * | 2019-03-22 | 2019-06-18 | 湖南科技大学 | 一种具有胀流特性的柔性磨具及其抛光方法 |
| CN112480335A (zh) * | 2020-11-18 | 2021-03-12 | 广州科莱瑞迪医疗器材股份有限公司 | 一种放射治疗用组织补偿胶及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5947874B2 (ja) | 2016-07-06 |
| EP2688938A1 (en) | 2014-01-29 |
| CA2829340A1 (en) | 2012-09-27 |
| BR112013024116A2 (pt) | 2016-12-13 |
| JP2014509612A (ja) | 2014-04-21 |
| EP2688938B1 (en) | 2019-10-16 |
| AU2011363043A1 (en) | 2013-09-26 |
| CA2829340C (en) | 2017-10-03 |
| KR20130139347A (ko) | 2013-12-20 |
| AU2011363043B2 (en) | 2015-05-14 |
| WO2012128751A1 (en) | 2012-09-27 |
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