CN111032664A - 有机改性的单甲硅烷基化合物、其制备及其应用 - Google Patents
有机改性的单甲硅烷基化合物、其制备及其应用 Download PDFInfo
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- CN111032664A CN111032664A CN201880054393.0A CN201880054393A CN111032664A CN 111032664 A CN111032664 A CN 111032664A CN 201880054393 A CN201880054393 A CN 201880054393A CN 111032664 A CN111032664 A CN 111032664A
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Abstract
如本文中限定的有机改性的单甲硅烷基化合物展现出优异的在宽的pH范围内的耐水解性和优异的润湿性质。所述有机改性的单甲硅烷基化合物有利地在各种各样的产品(例如农用化学组合物、助表面活性剂、涂料、个人护理产品和家庭护理产品)的任一种中作为润湿剂使用。
Description
相关申请的交叉引用
本申请要求在2017年8月21日提交的序列号为15/681,750美国申请的优先权，该美国申请的全部内容通过引用特此并入。
技术领域
本发明涉及在宽的pH范围内展现出耐水解性的有机改性的单甲硅烷基化合物。更具体地，本发明涉及在约2到约12范围pH内具有耐水解性的耐水解的有机改性的单甲硅烷基化合物。本发明还涉及这样的耐水解的有机改性的单甲硅烷基化合物作为农用(农业)、化妆、家庭护理和涂料组合物的组分。
背景技术
液体组合物对有生命和无生命物两者表面的局部施加以实现期望的变化牵涉控制性润湿、铺展、发泡、洗净(detergency)等过程。当以水溶液的形式使用以改善活性成分向被处理表面的输送时，已经发现，三硅氧烷型化合物在实现这些过程的控制以达到期望效果方面是有用的。然而，三硅氧烷化合物仅可在窄的pH范围(从略酸性的pH 6到非常温和的碱性pH 7.5的pH范围)内使用。在该窄的pH范围之外，三硅氧烷对于水解是不稳定的，经历快速分解。
在宽的pH范围内对于水解稳定的基于硅的表面活性剂是非常期望的，因为这样的化合物将容许组合物提供更有效的对有生命和无生命物两者表面的局部施加、较少量的水的使用、和/或在农用喷雾剂的有效性方面的提升。
发明内容
按照本发明，提供如下通式的有机改性的单甲硅烷基化合物：
R1-Si(CH3)2-Z
其中：
R1为含有至少两个甲基基团的5到8个碳原子的支化的一价烃基团；
Z为R2或R3；
R2为CH2CH2CH2-O-(C2H4-O)a(C3H6O)b(C4H8O)c-R4，其中R4为氢、1到约4个碳原子的线型或支化的一价烃基团、或者酰基，下标a为1到约20，下标b为0到约19，下标c为0到约19，并且下标a、b和c之和为1到约20；和，
R3为
其中R5为1到约4个碳原子的线型或支化的烃基团、或者乙酰基，并且X-为任选地包含1或2个羟基的2到约22个碳原子的饱和或不饱和的羧酸根阴离子。
本发明的有机改性的单甲硅烷基化合物可引入到许多类型的组合物(例如农用组合物、化妆组合物、家庭护理组合物和涂料组合物)中，其优异的在宽的pH范围内的稳定性和杰出的润湿性质向所述组合物赋予显著的功能优势。
具体实施方式
在本文的说明书和权利要求中，以下术语和表述应按指出的那样理解。
单数形式“一(种)”、“一(个)”和“所述(该)”包括复数，并且对具体数值的提及至少包括该具体值，除非上下文清楚地另外指明。
除了在工作实施例中或在另外指明的情况下之外，在说明书和权利要求书中记载的表示材料的量、反应条件、时间持续期、材料的定量性质等的所有数字应理解为在所有情形下均被术语“约”所修饰。
本文中描述的所有方法可按任意适合的次序实施，除非在本文中另外指明或明显地与上下文相悖。本文中提供的任意和所有实例或示例性语言(如“例如”)的使用仅旨在更好地说明本发明并且不对本发明的范围施加限制，除非另外主张。
说明书中的任何语言均不应解释为将任何未要求的要素指定为对本发明的实施是必要的。
术语“包含”、“包括”、“含有”、“其特征在于”及其语义等同物是包含性的或开放式术语，其不排除另外的未述及的要素或方法步骤，但是还将理解为包括更加限缩性的术语“由……组成”和“基本上由……组成”。
将理解，本文中记载的任何数量范围包括在该范围内的所有子范围以及这样的范围或子范围的不同端点的任意组合。
如本文中使用的，化学计量下标的整数值是指分子物种(种类，species)，而化学计量下标的非整数值是指以分子量平均值计、以数量平均值计、或以摩尔分数计的分子物种混合物。
将会进一步理解，在说明书中明确或隐含地公开和/或在权利要求中所述的作为属于在结构、组成和/或功能上相关的化合物、材料或物质的组的任意化合物、材料或物质包括该组的单独代表及其所有组合。
术语“佐剂”意指提升生物活性材料的效力的任意组合物、材料或物质。
术语“生物活性物”是指农用化学品或材料，其包括但不限于农药，例如除草剂、杀真菌剂、杀虫剂、杀螨剂和杀软体动物剂；植物养分；脱叶剂；以及，植物生长调节剂。
表述“烃基团”意指一个或多个氢原子已经从其除去的任意烃，并且包括烷基、烯基、炔基、环烷基、环烯基、环炔基、芳基、芳烷基和烷芳基(arenyl)基团并且包括含有至少一个杂原子的烃基团。
术语“烷基”意指任意一价的饱和的直链、支化或环状的烃基团；术语“烯基”意指含有一个或多个碳-碳双键的任意一价的直链、支化或环状的烃基团，其中该基团的连接位点可在碳-碳双键或其中的其它位置处；和，术语“炔基”意指含有一个或多个碳-碳三键和任选的一个或多个碳-碳双键的任意一价的直链、支化或环状的烃基团，其中该基团的连接位点可在碳-碳三键、碳-碳双键或其中的其它位置处。烷基的实例包括甲基、乙基、丙基和异丁基。烯基的实例包括乙烯基、丙烯基、烯丙基、甲基烯丙基、乙叉基降冰片烷、乙叉降冰片基、乙叉基降冰片烯和乙叉降冰片烯基。炔基的实例包括乙炔基、丙炔基和甲基乙炔基。
在有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的一些实施方式中，R1为支化的烷基CR6R7R8(CR9R10)m(CR11R12)nCHR13CH2-，其中R6、R7、R8、R9、R10、R11、R12和R13各自独立地为氢或甲基，R6、R7、R8、R9、R10、R11、R12和R13的2到4个为甲基，并且下标m和n各自独立地为0或1。
在有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的其它实施方式中，R1包含2到4个甲基，CR6R7R8为H3C-、(H3C)2CH-或(H3C)3C-，下标m和/或n为0，Z为R2且R2为-CH2CH2CH2-O-(C2H4O)a(C3H6O)b-R4，其中R4为氢、1到4个碳原子的线型或支化的烷基、或者酰基，下标a为1到约20、优选地2到约15、和更优选地4到约10，下标b为0或1到约10、优选地0或1到约6、和更优选地0或1到约4，并且下标a和b之和为1到约20、优选地2到约15、和更优选地4到约10。
在有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的还更其它的实施方式中，R1包含2到4个甲基，CR6R7R8为H3C-、(H3C)2CH-或(CH3)3C-，m为0或1，n为0，Z为R2且R2为-CH2CH2CH2-O-(C2H4O)a-R4，其中R4为氢、1到4个碳原子的线型或支化的烷基、或者酰基，并且下标a为1到约20、优选地2到约15、和更优选地4到约10。
在有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的进一步的实施方式中，CR6R7R8为H3C-、(H3C)2CH-或(H3C)3C-，m和/或n为0或1，Z为R3且R3为
其中R5为1到约4个碳原子的线型或支化的烷基，并且X-如前面定义的。
在有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的还更进一步的实施方式中，R1包含2到4个甲基，CR1R2R3为(H3C)2CH-或(H3C)3C-，m为0或1，n为0，Z为R3且R3为
其中R5为1到约4个碳原子的线型或支化的烷基，并且X-为任选地包含1或2个羟基的2到约22个碳原子、优选地2到约10个碳原子、和更优选地2到6个碳原子的羧酸根阴离子。
在本文的有机改性的单甲硅烷基化合物的具体实施方式中，X-为如下的阴离子：单羧酸，例如乙酸、丙酸或丁酸；二元羧酸，例如琥珀酸、马来酸或草酸；三元羧酸；α-羟基酸，例如乙醇酸、乳酸、柠檬酸或扁桃酸；β-羟基酸，例如羟基丙酸、水杨酸、肉毒碱、β-羟基β-甲基丁酸或3-羟基丁酸；二羟基酸，例如二羟甲基丙酸；或者，饱和或不饱和的脂肪酸，例如辛酸、癸酸、己酸、油酸、肉豆蔻油酸、硬脂酸、亚油酸或芥酸。
A.用于制备有机改性的单甲硅烷基化合物的方法
本发明的有机改性的单甲硅烷基化合物可通过若干种合成工艺的任一种而制备，所述合成工艺的要求在本领域中是公知的。
根据本发明的有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的一种制备方法，使至少一种支化的烯烃和二甲基甲硅烷基氯化物在催化性氢化硅烷化反应条件下反应以提供氯硅烷加合物，然后使其经历还原以提供相应的甲硅烷基氢化物(silylhydride)中间体。可用于制备在本文的有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的制备中使用的前述氯硅烷加合物和甲硅烷基氢化物中间体的支化的烯烃包括例如以下烯烃及其混合物：
用于提供甲硅烷基氢化物中间体的氯硅烷加合物(包括其混合物)的还原可使用本领域中公知的各种金属络合物(例如金属如铝、锂、镍、钯或铂的络合物)的任意种而便利地实施。很多种用于卤代硅烷的还原的铝催化剂是已知的并且这样的络合物可用于产生本文中的氢化物中间体。在一个实施方式中，所述金属络合物为有机铝化合物双(2-甲氧基乙基)铝氢化钠，其可作为Vitride(Vertellus)或Red-Al(Sigma-Aldrich)在市场上获得。
所述氢化物中间体与一种或多种烯丙基-或甲基烯丙基-醚或聚醚(例如具有通式H2C＝CR13CH2-O-(C2H4O)a(C3H6O)b(C4H8O)c-R4，其中R4为氢或甲基并且R13以及下标a、b和c如前面定义的)的反应在催化性氢化硅烷化反应条件下实施以提供本发明的醚/聚醚-改性的单甲硅烷基化合物。
用于提供本发明的醚/聚醚-改性的单甲硅烷基化合物的可与甲硅烷基氢化物中间体反应的适合的烯属改性的醚/聚醚(包括其混合物在内)包括烯丙基丙基醚、甲基烯丙基丙基醚、聚乙二醇烯丙基醚、聚乙二醇聚丙二醇烯丙基醚、聚丙二醇烯丙基醚、甲氧基聚乙二醇烯丙基醚、甲氧基聚乙二醇聚丙二醇烯丙基醚、丁氧基聚乙二醇聚丙二醇烯丙基醚、甲氧基聚丙二醇烯丙基醚、丁氧基聚丙二醇烯丙基醚、聚乙二醇聚丁二醇烯丙基醚、聚乙二醇聚丙二醇聚丁二醇烯丙基醚、及它们的混合物。烯丙基-和甲基烯丙基-封端的聚醚包括无规和嵌段型的那些。
氢化硅烷化催化剂及它们的使用在本领域中是公知的，并且包括金属例如铑、钌、钯、锇、铱和铂的络合物。很多种含铂的氢化硅烷化催化剂均可在本文中使用，例如如在美国专利No.3,159,601中记载的具有式PtCl2烯烃和HPtCl3烯烃的那些，该美国专利通过引用特此并入。其它的含铂的氢化硅烷化催化剂包括如在美国专利No.3,220,972中记载的具有至多2摩尔/克铂的氯铂酸和醇、醚、醛的络合物及其混合物，该美国专利通过引用特此并入。在制备本发明的有机改性的甲硅烷基化的化合物中可使用的另外的含铂的氢化硅烷化催化剂记载于美国专利No.3,715,334、3,775,452和3,814,730中(Karstedt催化剂)，所述美国专利通过引用特此并入。关于氢化硅烷化的进一步的背景可见于J.L.Spier的“Homogeneous Catalysis of Hydrosilylation by Transition Metals”,Advances inOrganometallic Chemistry,第17卷,第407-447页,F.G.A.Stone和R.West编辑,AcademicPress出版(New York,1979)，其通过引用特此并入。本领域技术人员对于给定的氢化硅烷化反应能够容易地确定催化剂的有效量。通常，对于期望的氢化硅烷化，在约0.1到50重量百万分率的范围内的氢化硅烷化催化剂的量将是令人满意的。
以3,3-二甲基-丁-1-烯进行说明，用于制备本发明的醚/聚醚-改性的单甲硅烷基化合物的一个工艺可被认为如下进行：
以下本发明的醚/聚醚-改性的单甲硅烷基化合物可按照上述合成制备：
按照用于制备有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的另一工艺、特别是提供本发明的季铵-改性的单甲硅烷基化合物的工艺，使如上所示获得的甲硅烷基氢化物中间体与缩水甘油基醚和/或甲基烯丙基缩水甘油基醚反应，随后与烷基二甲基季铵盐、或所需酸X和烷基二甲基叔胺的季铵形成用混合物(quat-forming mixture)进行开环反应，如以下反应方案所说明的：
以下本发明的季铵改性的单甲硅烷基化合物R1-Si(CH3)2-Z可按照上述合成制备：
B.包含有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的组合物
本发明的有机改性的单甲硅烷基化合物可单独地或以其组合以如下的多种形式使用：作为液体溶液、固体在液体中的分散体、液体在液体中的分散体、固体混合物或固溶体等。组合物通常会包含润湿剂有效量的本发明的一种或多种有机改性的甲硅烷基化合物R1-Si(CH3)2-Z，例如，取决于给定组合物的具体意图或用途，基于所述组合物的重量约0.01到约99、和有利地约0.1到约50重量百分比的有机改性的甲硅烷基化合物。
1.农用化学组合物
很多农药应用需要将佐剂加入到喷雾剂混合物以提供叶子表面上的润湿和铺展。通常该佐剂为表面活性剂，其能发挥多个功能，例如提升在难以润湿的叶子表面上的喷雾液滴保留性、增强铺展以改善喷雾剂覆盖、或提供除草剂向植物表皮中的渗透。所述佐剂作为桶边(桶混，tank-side)添加剂提供、或作为农药配制剂中的组分使用。
农药的典型用途包括农业、园艺、草皮、观赏植物、庭院、兽用和林业应用。本发明的农药组合物还包括至少一种农药，其中本发明的季铵有机硅表面活性剂按足以向最终使用浓度递送0.005至2重量百分比农药的量作为浓缩物存在或在桶混中稀释。任选地，农药组合物可包括赋形剂、助表面活性剂、溶剂、泡沫控制剂、沉积辅助剂、漂移阻滞剂、生物制剂、微量营养素、肥料等。术语农药意指用于消灭害虫的任意化合物，例如灭鼠剂、杀虫剂、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、有丝分裂破坏剂、脂类生物合成抑制剂、细胞壁抑制剂和细胞膜破坏剂。在本发明组合物中使用的农药量随所使用的农药类型而变。可与本发明组合物并用的农药化合物的更具体实例为但不限于除草剂和生长调节剂，例如：苯氧基乙酸、苯氧基丙酸、苯氧基丁酸、苯甲酸、三嗪和均三嗪、取代的脲、尿嘧啶、苯达松、甜菜安(desmedipham)、灭草唑、甜菜宁、哒草特、杀草强、广灭灵、氟啶草酮、达草灭(norflurazone)、二硝基苯胺、异乐灵、氨磺乐灵、二甲戊乐灵、氨氟乐灵、氟乐灵、草甘膦、磺酰脲、咪唑啉酮、烯草酮、禾草灵-甲基，
唑禾草灵-乙基、吡氟禾草灵-对丁基、吡氟氯禾灵-甲基、喹禾灵、稀禾定、敌草腈、异
酰草胺和联吡啶
化合物。
可与本发明一起使用的杀真菌剂组合物包括但不限于，杀螟丹、克啉菌、十二环吗啉、烯酰吗啉；氟硅唑、戊环唑、环唑醇、氟环唑、呋菌唑、丙环唑、戊唑醇等；抑霉唑、托布津、苯菌灵、多菌灵、百菌清、氯硝胺、肟菌酯、氟嘧菌酯(fluoxystrobin)、醚菌胺、嘧菌酯、灭菌胺(furcaranil)、咪鲜胺、磺菌胺、恶唑菌酮、克菌丹、代森锰、代森锰锌、多地辛、多果定和甲霜灵。
可与本发明组合物一起使用的杀虫剂(其包括杀幼虫剂、杀螨药和杀卵剂化合物)不限于，苏云金芽孢杆菌、多杀菌素、阿维菌素、多拉菌素、雷皮菌素、除虫菊酯、甲萘威、抗蚜威(primicarb)、涕灭威、灭多威、双甲脒、硼酸、杀虫脒、甲硝脲、双氟脲、灭氟脲、除虫脲、吡虫啉、二嗪农、乙酰甲胺、硫丹、凯夫兰、乐果、益棉磷、谷硫磷、异
唑磷(izoxathion)、毒死蜱、氯苯噻嗪、高效氯氟氰菊酯、氯菊酯、联苯菊酯、氯氰菊酯等。
2.肥料和微量营养素
肥料或微量营养素包括但不限于，硫酸锌、硫酸亚铁、硫酸铵、尿素、脲铵氮、硫代硫酸铵、硫酸钾、磷酸一铵、磷酸脲、硝酸钙、硼酸、硼酸的钾和钠盐、磷酸、氢氧化镁、碳酸锰、多硫化钙、硫酸铜、硫酸锰、硫酸铁、硫酸钙、钼酸钠、氯化钙。
所述肥料或微量营养素可为液体或固体。如果其为固体，则如下是优选的：在施加之前它在溶剂或本发明的季铵有机硅表面活性剂中是可溶解的，并且所述有机硅可充当溶剂、或者对于这样的溶解性的表面活性剂或另外的表面活性剂可实现该功能。
3.农用赋形剂
在本发明组合物中还可包括缓冲剂、防腐剂和本领域中知晓的其它标准农用赋形剂。
在本发明组合物中还可包括溶剂。所述溶剂在室温下为液态。实例包括水、醇、芳族溶剂、油(即矿物油、植物油、硅油等)、植物油的低级烷基酯、脂肪酸、酮、二醇(glycol)、聚乙二醇、二元醇(diol)、石蜡类(paraffinic)等。具体溶剂将为如美国专利No.5,674,832(其通过引用特此并入)中说明的2,2,4-三甲基-1,3-戊烷二醇及其烷氧基化的(特别地乙氧基化的)形式，或N-甲基-吡咯烷酮。
4.助表面活性剂
在本文的组合物中可使用的助表面活性剂包括非离子型、阳离子型、阴离子型、两性、两性离子型、聚合物型表面活性剂、或它们的任意混合物。表面活性剂典型地为基于烃的、基于有机硅的、或基于碳氟化合物的。
而且，如美国专利No.5,558,806中描述的不妨碍超铺展的具有短链疏水基的其它助表面活性剂也是可用的，该美国专利通过引用并入本文中。
可用的表面活性剂包括，包含嵌段共聚物(包括环氧乙烷、环氧丙烷、环氧丁烷及其混合物的共聚物)的烷氧基化物，特别是乙氧基化物；烷基芳基烷氧基化物(特别地乙氧基化物或丙氧基化物)和它们的衍生物(其包括烷基苯酚乙氧基化物)；芳基芳基烷氧基化物(特别地乙氧基化物或丙氧基化物)和它们的衍生物；胺烷氧基化物(特别地胺乙氧基化物)；脂肪酸烷氧基化物；脂肪醇烷氧基化物；烷基磺酸盐；烷基苯和烷基萘磺酸盐；硫酸化的脂肪醇、胺或酰胺；羟乙基磺酸钠的酸酯；磺基琥珀酸钠的酯；硫酸化或磺酸化脂肪酸酯；石油磺酸盐；N-酰基肌氨酸盐；烷基多糖苷；烷基乙氧基化胺；等。
具体实例包括烷基炔属二醇(SURFONYL-Air Products)、基于吡咯烷酮的表面活性剂(例如SURFADONE–LP 100–Ashland)、硫酸2-乙基己基酯、异癸基醇乙氧基化物(例如RHODASURF DA 530–Rhodia)、乙二胺烷氧基化物(TETRONICS–BASF)、环氧乙烷/环氧丙烷共聚物(PLURONICS–BASF)、挛连(Gemini)型表面活性剂(Rhodia)和二苯基醚挛连型表面活性剂(例如DOWFAX–Dow Chemical)。
优选的表面活性剂包括环氧乙烷/环氧丙烷共聚物(EO/PO)；胺乙氧基化物；烷基多糖苷；氧代-十三烷基醇乙氧基化物，等。
在一种优选的实施方式中，本发明的农用化学组合物进一步包括一种或多种农用化学成分。适合的农用化学成分包括但不限于除草剂、杀虫剂、生长调节剂、杀真菌剂、杀螨药、杀螨剂、肥料、生物制剂、植物养料、微量营养素、生物杀灭剂、石蜡矿物油、甲基化种籽油(即大豆脂肪酸甲酯或芥花脂肪酸甲酯(methyl canolate))、植物油(例如大豆油和芥花油)、水调理剂例如
(Loveland Industries,Greeley,CO)和
(HelenaChemical,Collierville,TN)、改性粘土例如
(BASF)、泡沫控制剂、表面活性剂、润湿剂、分散剂、乳化剂、沉积助剂、抗漂移组分和水。
适合的农用化学组合物通过将以上组分的一种或多种与本发明的季铵有机硅表面活性剂按本领域中知晓的方式(例如通过混合)合并作为桶混合物(桶混，tank-mix)或作为“罐装(配方，in-can)”配制剂而制成。术语“桶混(合物)”意指在使用时将至少一种农用化学品加入到喷雾剂介质例如水或油。术语“罐装”是指包含至少一种农用化学组分的配制剂或浓缩物。于是，“罐装”配制剂可在使用时典型地在桶混中稀释到使用浓度，或其可在未稀释的情况下使用。
5.涂料组合物
典型地，出于乳化、组分增容、整平、流动和减少表面缺陷的意图，涂料配制剂需要润湿剂或表面活性剂。另外，所述添加剂可提供固化的或干膜的改善，例如改善的耐磨性、抗粘连、亲水、和疏水性质。涂料配制剂可作为溶剂型涂料、水型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，例如工业维护涂料和船舶涂料；
典型的树脂类型包括：聚酯、醇酸树脂、丙烯酸类、环氧类和聚氨酯。
6.个人护理产品
在一种优选实施方式中，本发明的季铵有机硅表面活性剂包括按100重量份(“pbw”)个人护理组合物计0.1到99pbw、更优选地0.5pbw至30pbw、和甚至更优选地1到15pbw的季铵有机硅表面活性剂以及1pbw至99.9pbw、更优选地70pbw至99.5pbw、和甚至更优选地85pbw至99pbw的个人护理组合物。
本发明的甲硅烷基化的表面活性剂组合物可在个人护理乳液例如香波和调理剂以及洗剂和乳膏中使用。
其中可使用本发明的甲硅烷基化的表面活性剂组合物和源自其的本发明的有机硅组合物的个人护理应用品包括但不限于体香剂，止汗剂，止汗剂/体香剂，剃须产品，皮肤洗剂，保湿剂，爽肤水(收敛剂)，沐浴产品，清洗产品，毛发护理产品例如香波、调理剂、摩丝、定型凝胶、喷发剂、染发剂、发色产品、毛发漂白剂、烫发产品、直发剂，美甲产品例如指甲油,指甲油去除剂、指甲膏和洗剂、表皮软化剂，防护性乳膏例如防晒霜、驱虫和抗老化产品，彩妆品例如唇膏、粉底、扑面粉、眼线膏、眼影、腮红、化妆品、睫毛膏和常规上一直添加有机硅组分的其它个人护理配制剂，以及用于局部施加待施加到皮肤的药用组合物的药物递送体系。
在一种优选实施方式中，本发明的个人护理组合物进一步包括一种或多种个人护理成分。适合的个人护理成分包括例如润肤剂、保湿剂、增湿剂、颜料(包括珠母般颜料例如氯氧化铋和二氧化钛涂覆的云母)、着色剂、香料、杀生物剂、防腐剂、抗氧化剂、抗微生物剂、抗真菌剂、止汗剂、剥离素、激素、酶、药用化合物、维生素、盐、电解质、醇、多元醇、用于紫外辐射的吸收剂、植物提取物、表面活性剂、硅油、挥发性有机硅、有机油、蜡、成膜剂、增稠剂例如气相二氧化硅或水合二氧化硅、颗粒填料例如滑石、高岭土、淀粉、改性淀粉、云母、尼龙、粘土例如膨润土和有机改性的粘土。
适合的个人护理组合物通过将以上组分的一种或多种与甲硅烷基化的表面活性剂组合物按本领域中知晓的方式(例如通过混合)进行组合而制成。适合的个人护理组合物可为单相的形式，或其中有机硅相可为不连续相或连续相的乳液(包括水包油型、油包水型和无水乳液)以及多重乳液例如油包水包油型乳液和水包油包水型乳液的形式。
在另一有用的实施方式中，皮肤护理组合物包括本发明的甲硅烷基化的表面活性剂组合物和载剂例如硅油或有机油。皮肤护理组合物可任选地进一步包括润肤剂例如甘油三酯、蜡酯、脂肪酸的烷基或烯基酯或多羟基醇酯，以及常规上在皮肤护理组合物中使用的一种或多种已知组分例如颜料，维生素例如维生素A、维生素C和维生素E，防晒霜或遮光化合物例如二氧化钛、氧化锌，氧苯酮，肉桂酸辛基甲氧基酯，丁基甲氧基二苯甲酰甲烷，对氨基苯甲酸，和辛基二甲基-对氨基苯甲酸。
在另一有用的实施方式中，彩妆组合物例如唇膏、化妆品或睫毛膏组合物包括甲硅烷基化的表面活性剂组合物以及着色试剂例如颜料、水溶性染料或脂溶性染料。
本发明组合物的用途不限于个人护理组合物，还可联想到其它产品例如蜡、抛光剂和通过本发明组合物处理的纺织品。
7.家庭护理产品
家庭护理应用包括衣物洗涤剂和织物软化剂、洗洁精、木材和家具上光剂、地板上光剂、浴缸和瓷砖清洁剂、抽水马桶清洁剂、硬表面清洁剂、窗户清洁剂、防雾剂、下水道清洁剂、自动洗碟洗涤剂和展开剂(sheeting agent)、地毯清洁剂、预洗除污剂、锈迹清洁剂和除垢剂。
下面的实施例对本发明的有机改性的甲硅烷基化的表面活性剂、其制备、其性质、及其在除草剂组合物中的用途进行说明。
实施例1：氯硅烷加合物的制备
将2000mL四颈圆底烧瓶用磁力搅拌棒、带有氮气进口的回流冷凝器、热电偶、滴液漏斗和加热套进行装配。在15℃在N2下向所述烧瓶加入3,3-二甲基-1-丁烯(170.69g，2.02mol，99.6重量百分比的纯度)和Karstedt催化剂(5ppm)。将所述烧瓶温热到35℃，将二甲基甲硅烷基氯化物(192.08g，2mol，98.5重量百分比的纯度)加入到滴液漏斗，并滴加到所述圆底烧瓶。注意立刻放热。在2.5小时内继续加入二甲基甲硅烷基氯化物。在加入后，将反应维持在40℃3小时，并然后通过气相色谱法进行分析。发现：转化为氯硅烷加合物的转化率>95％。
实施例2：氢化物中间体的制备
将实施例1的氯硅烷加合物冷却到1℃。将二氢-双(2-甲氧基乙氧基)铝酸钠的溶液(Vitride，甲苯中61.8重量百分比；359.83g的溶液，1.1mol)加入到滴液漏斗并将其以维持反应温度<5℃的速率滴加到所述氯硅烷的溶液(总的加入时间～3.5小时)。在加入完成之后，将反应混合物搅拌并缓慢地容许其温热到室温(～12小时)。最后，向该反应混合物加入275g一缩二乙二醇二丁基醚并在真空下汽提。收集澄清无色的产物作为50重量百分比的在甲苯中的溶液。将产物通过气相色谱法进行分析并发现其已经经历定量转化为期望的还原产物。
实施例3-7；对比例1-3：有机改性的单甲硅烷基化合物的制备
进一步将实施例2的氢化物中间体用各种烯丙基聚氧化亚烷基进行改性以产生本发明的有机改性的单甲硅烷基化合物(表1)以及落在本发明范围之外的用于对比意图的若干种化合物(表2)。
本发明的有机改性的单甲硅烷基化合物以及用于对比意图而制备的化合物通过例如在Bailey的美国专利No.3,299,112中记载的铂-介导的氢化硅烷化的常规方法而获得，该美国专利通过引用并入本文中。一种代表性的合成叙述于下。
将100mL圆底烧瓶用磁力搅拌棒、带有氮气进口的回流冷凝器、热电偶、滴液漏斗和加热套装配。将具有约350g/mol平均分子量的烯丙基聚醚(3.5g；0.01mol)、氯铂酸(5ppm)和丙酸钠(3.5mg)加入到所述圆底烧瓶、搅拌并使其达到85℃。将碳硅烷(实施例2)在甲苯中的溶液(15g的8重量百分比的溶液；0.00833mol碳硅烷)加入到滴液漏斗并滴加到所述烧瓶。注意立即放热，在45分钟内继续加入。在完全加入之后，将反应在85℃维持5小时。测试反应产物的Si-H含量并表明0cc H2/g的剩余。将反应混合物汽提(～10mm Hg，100℃)1.5小时以除去挥发物，容许其冷却到<40℃，用硅藻土和碳酸氢钠处理，搅拌，加压过滤，并装瓶。产率：4g澄清的棕色液体。
下表1列出本发明的符合如下一般结构的经聚醚-改性的单甲硅烷基化合物：
(CH3)3C(CH2)2Si(CH3)2CH2CH2CH2-O-(CH2CH2O)a(CH2CH(CH3)O)b R4
其中下标a和b以及基团R4为如在其中所说明的。
表1：本发明化合物
| 化合物 | 下标a | 下标b | R<sup>4</sup> |
| 实施例3 | 7.5 | 0 | CH<sub>3</sub> |
| 实施例4 | 7.5 | 0 | H |
| 实施例5 | 4 | 0 | H |
| 实施例6 | 11 | 0 | H |
| 实施例7 | 5 | 2.5 | H |
表2列举在本发明范围之外并符合如下的一般结构的三种有机改性的单甲硅烷基化合物：
(CH3)3Si(CH2)2Si(CH3)2CH2CH2CH2-O-(CH2CH2O)c Y
其中下标b和基团Y为如在其中所说明的。对比例1-3的化合物各自与本发明的化合物的不同之处在于键合到硅原子的烷基的种类(nature)，具体在于与在烷基中必须包含至少5个且最高达8个碳原子的本发明化合物相比，其在烷基中具有仅4个碳原子。
表2：对比性的有机改性的单甲硅烷基化合物
| 化合物 | 下标c | Y |
| 对比例1 | 7.5 | CH<sub>3</sub> |
| 对比例2 | 7.5 | H |
| 对比例3 | 11 | H |
实施例8：季铵-改性的单甲硅烷基化合物(QC-1)的制备
下面的反应方案显示使用已知且常规的合成程序的季铵-改性的单甲硅烷基化合物的制备：
将26g(0.1mol)以上所示的单环氧官能的单甲硅烷基化合物、10.39g(0.1mol)的N,N'-二甲基氨基丙醇、13.86g(0.1mol)二羟甲基丙酸和16.75g一缩二丙二醇溶剂加入到设置有冷凝器和氮气罩(blanket)的三颈烧瓶中。将所述混合物快速地加热到80-82℃并连续地搅拌18小时。之后将烧瓶冷却到室温以获得以上提到的季铵改性的单甲硅烷基化合物(H3C)3CCH2CH2-Si
[(CH2OH)2(CH3)C-COO-]以75wt％在一缩二丙二醇中的棕色粘稠溶液。
实施例9：有机改性的单甲硅烷基化合物R1-Si(CH3)2-Z的铺展性质
铺展通过如下而测定：在50至70％之间的相对湿度(在22到25℃)，将表面活性剂溶液的10μL液滴施加到聚苯乙烯培养皿(Fisher Scientific)并在30秒之后测量铺展直径(mm)。通过自动移液管施加所述溶液以提供可再现体积的液滴。使用通过微孔过滤系统进一步纯化的去离子水制备表面活性剂溶液。
表3表明，本发明的化合物(实施例3-8)提供与对比性化合物(对比例1-3)类似的铺展性质。另外，随聚乙烯含量从约4个EO增至7.5个EO增至11个EO单元(比较实施例6与实施例2的结果)，本发明化合物的铺展相应地增大。
表3：化合物的铺展性质
实施例10：有机改性的单甲硅烷基化的化合物的水解稳定性
使用铺展作为稳定性指标测定本发明代表性化合物的水解稳定性。公知的是，在暴露到低pH环境(例如pH为3)时，有机硅表面活性剂的水解随温度时间显著减少。
根据实施例1中描述的方法测定铺展。在去离子水(～pH 5)和pH为3的缓冲溶液(Fischer Scientific)中制备表面活性剂溶液。
表4表明，本发明的有机改性的单甲硅烷基化合物在pH 3和pH 4下是耐水解的。铺展在测试期内基本上不变。
表4：pH对有机改性的甲硅烷基化合物的水解稳定性的影响
| 化合物 | 初始 | 24h | 5d | 30d | 90d |
| 对比例1 | 55 | 52 | 49 | nd | nd |
| 对比例1，在pH 3缓冲液中 | 49 | 45 | 42 | nd | 42 |
| 实施例4 | 41 | 46 | 41 | nd | nd |
| 实施例4，在pH 3缓冲液中 | 44 | 39 | 37 | 47 | 47 |
| 实施例4，在pH 4缓冲液中 | 45 | nd | nd | 47 | 46 |
实施例11：2,4-D-二甲基胺盐在油菜叶中的摄取
根据Lui在Pro.18th Asian-Pacific Weed Sci.Soc.Conf.,pp.561-566.Liu,ZQ；2001中记载的方法，在油菜中在2HAT和24HAT(处理后的小时数)时测定[C14]-2,4-二氯苯氧基乙酸二甲基胺盐(2,4-D DMA盐)(1％a.e./100L/ha)的摄取。
表6表明，本发明的有机改性的单甲硅烷基化合物相对于对比例1的化合物显示出相当的或改善的2,4-D二甲基胺在油菜叶中的摄取。
表6：[C14]-2,4-D,DMA盐在油菜叶中的摄取
具有共同后标(postscript)的平均值不是有显著差异的(p＝0.05)。
实施例12：喷雾液滴粘附对油菜叶上的总可用剂量的影响
通过动力系统经由喷雾喷嘴产生喷雾液滴。将化合物加入到喷雾混合物可帮助减小表面张力，容许液滴粘附到目标叶子。然而，并非所有化合物均促进相同水平的液滴粘附，且因此喷雾的仅一部分粘附到叶子。其余的喷雾可从所述叶子弹开，使得期望的农用化学品(即除草剂、杀真菌剂、肥料等)的递送低效。
总可用剂量(TAD)将农用化学品的摄取和喷雾液滴粘附两者纳入考虑。该TAD为递送到植物表面(粘附，Adhesion)的可供摄取(摄取，Uptake)到叶子中的材料量。基本上，TAD＝摄取(％)X液滴粘附(％)。TAD越高，摄取潜力(可能性)越高。
如以前所记载的(Stevens等人，1993)，使用具有200μm喷嘴孔的压电液滴发生器形成大约450μm的单尺寸液滴来测定雾滴粘附(以受冲击的液滴的a％)。液滴自由下落距离为53cm。使用油菜叶子(难以润湿的)作为冲击表面，其中叶角(叶倾角)为22.5°。
使用去离子水制备本发明化合物和对比例1化合物的溶液(0.15％)。溶液还包含作为除草剂的2,4-D DMA盐(1％)。
TAD的测定使用来自前面实施例的摄取结果(表7)以及表6中报告的粘附结果。
下表7表明，本发明的有机改性的单甲硅烷基化合物相对于对比性化合物提供近似或更好的在油菜叶上的液滴粘附。然而，本发明化合物提供比对比例1化合物高的TAD。
表7：液滴粘附对2,4-D DMA在油菜叶中的总可用剂量的影响
具有共同后标的平均值不是有显著差异的(p＝0.05)。
尽管参考具体实施方式已经对本发明进行描述，但是本领域技术人员将理解，可作出各种各样的改变并可对其要素用等同物进行替代而不偏离本发明的范围。希望，本发明不受限于所公开的具体实施方式，而是它涵盖落在所附权利要求的范围内的所有实施方式。
Claims (21)
1.如下通式的有机改性的单甲硅烷基化合物：
R1-Si(CH3)2-Z
其中：
R1为含有至少两个甲基基团的5到8个碳原子的支化的一价烃基团；
Z为R2或R3；
R2为CH2CH2CH2-O(C2H4-O)a(C3H6O)b(C4H8O)c-R4，其中R4为氢、1到约4个碳原子的线型或支化的一价烃基团、或者酰基，下标a为1到约20，下标b为0到约19，下标c为0到约19，并且下标a、b和c之和为1到约20；和
R3为
[X-]，其中R5为1到约4个碳原子的线型或支化的烃基团、或者乙酰基，并且X-为含有0到2个羟基的2到约22个碳原子的饱和或不饱和的羧酸根阴离子。
2.如权利要求1所述的有机改性的单甲硅烷基化合物，其中R1为支化的烷基CR6R7R8(CR9R10)m(CR11R12)nCHR13CH2-，其中R6、R7、R8、R9、R10、R11、R12和R13各自独立地为氢或甲基，R6、R7、R8、R9、R10、R11、R12和R13中的2到4个为甲基，并且下标m和n各自独立地为0或1。
3.如权利要求2所述的有机改性的单甲硅烷基化合物，其中R1包含2到4个甲基，CR6R7R8为H3C-、(H3C)2CH-或(H3C)3C-，下标m和/或n为0，Z为R2且R2为-CH2CH2CH2-O-(C2H4O)a(C3H6O)b-R4，其中R4为氢、1到4个碳原子的线型或支化的烷基、或者酰基，下标a为1到约20，下标b为0到约10，并且下标a和b之和为1到约20。
4.如权利要求3所述的有机改性的单甲硅烷基化合物，其中下标a为2到约15。
5.如权利要求3所述的有机改性的单甲硅烷基化合物，其中下标a为4到约10。
6.如权利要求3所述的有机改性的单甲硅烷基化合物，其中下标b为0到约6。
7.如权利要求4所述的有机改性的单甲硅烷基化合物，其中下标b为0到约6，并且下标a和b之和为2到约15。
8.如权利要求5所述的有机改性的单甲硅烷基化合物，其中下标b为0到约4，并且下标a和b之和为约4到约10。
9.如权利要求2所述的有机改性的单甲硅烷基化合物，其中R1包含2到4个甲基，CR6R7R8为H3C-、(H3C)2CH-或(H3C)3C-，m和/或n为0或1，Z为R3且R3为
[X-]，其中R5为1到约4个碳原子的线型或支化的烷基。
10.如权利要求2所述的有机改性的单甲硅烷基化合物，其中R1包含2到4个甲基，CR1R2R3为(H3C)2CH-或(H3C)3C-，m为0或1，n为0，Z为R3且R3为
[X-]，其中R5为1到约4个碳原子的线型或支化的烷基，并且X-为0到2个羟基和2到约10个碳原子的羧酸根阴离子。
11.如权利要求10所述的有机改性的化合物，其中X-为0到2个羟基和2到约6个碳原子的羧酸根阴离子。
12.如权利要求2所述的有机改性的单甲硅烷基化合物，其为选自如下的至少一种醚-或聚醚-改性的单甲硅烷基化合物：
13.如权利要求2所述的有机改性的单甲硅烷基化合物，其为选自如下的至少一种季铵-改性的单甲硅烷基化合物：
14.农用化学组合物、助表面活性剂、涂料、个人护理产品或家庭护理产品，其包括润湿剂有效量的至少一种如权利要求1所述的有机改性的单甲硅烷基化合物。
15.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求2所述的有机改性的单甲硅烷基化合物。
16.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求3所述的有机改性的单甲硅烷基化合物。
17.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求6所述的有机改性的单甲硅烷基化合物。
18.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求9所述的有机改性的单甲硅烷基化合物。
19.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求10所述的有机改性的单甲硅烷基化合物。
20.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求12所述的有机改性的单甲硅烷基化合物。
21.农用化学组合物，其包括润湿剂有效量的至少一种如权利要求13所述的有机改性的单甲硅烷基化合物。
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|---|---|
| NZ761475A (en) | 2024-03-22 |
| AU2018321549B2 (en) | 2021-12-23 |
| AU2018321549A1 (en) | 2020-02-27 |
| EP3652185A1 (en) | 2020-05-20 |
| WO2019040110A1 (en) | 2019-02-28 |
| EP3652185B1 (en) | 2021-08-04 |
| CN111032664B (zh) | 2024-01-30 |
| US20190055271A1 (en) | 2019-02-21 |
| US10233200B2 (en) | 2019-03-19 |
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