CN1252091A - 洗涤剂化合物 - Google Patents

洗涤剂化合物 Download PDF

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CN1252091A
CN1252091A CN 98804060 CN98804060A CN1252091A CN 1252091 A CN1252091 A CN 1252091A CN 98804060 CN98804060 CN 98804060 CN 98804060 A CN98804060 A CN 98804060A CN 1252091 A CN1252091 A CN 1252091A
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cationic surfactant
poly
polyamine
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S·W·海因兹曼
B·T·因格拉姆
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Procter and Gamble Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
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    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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    • C11D1/65—Mixtures of anionic with cationic compounds

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Abstract

本发明涉及含有至少一个季铵基团和至少一个伯、仲或叔胺基团的阳离子表面活性剂。该表面活性剂可以用于任何需要表面活性的应用中。它们尤其可以用于清洗或洗涤剂组合物或其组分中。

Description

洗涤剂化合物
                     技术领域
本发明涉及含有至少一个季铵基团和至少一个伯、仲或叔胺基团的聚胺阳离子表面活性剂及其制备方法。该表面活性剂可以用于任何需要表面活性的应用中。具体地，它们可以用于清洗或洗涤剂组合物或其组分中。
                     发明背景
令人满意地除去油脂污垢/污渍(即具有高比例甘油三酯或脂肪酸的污垢/污渍)是用于洗衣和洗餐具方法中的洗涤剂组合物配方师所面临的一个复杂问题。在洗涤剂产品中已经常规地使用了表面活性剂组分以便有助于除去这样的油脂污垢/污渍。具体地，对于用于除去油脂污垢/污渍，已经描述了包括阳离子的表面活性剂体系。
在文献中可以发现用于洗涤剂的表面活性剂的很多选择，但现实是：很多这样的表面活性剂由于其具有某些性质(例如在酸性或碱性环境中的不稳定性、与漂白剂的不相容性、异味问题、可生物降解性问题)，所以它们为并不总是适合于洗涤剂的化学品。因此，这些各种因素增加了洗涤剂制造商寻求改进性能的困难。例如，某些不能生物降解的组分已经不受欢迎了。结果制造商比文献建议的有效的并可得到的组分选择(范围)多少有更多的限制。
各种阳离子表面活性剂被建议用于洗涤剂中。一类被广泛研究的阳离子表面活性剂是由季铵或咪唑化合物组成的，它们通常被设计成用于特殊的用途。例如，已经建议了各种季铵表面活性剂用于洗发剂组合物中并且据说将化妆品益处提供给了头发。
US-A-4228042公开了可生物降解的阳离子表面活性剂，包括用于洗涤剂组合物中以便提供去除油脂/油质污垢的阳离子酯表面活性剂。例如，US3567729公开了用于洗涤剂中的二季铵化合物。例如，US5068431描述了含有两性氧化胺基团的季铵化合物。
本申请人现已发现：某些含有至少一个带阳离子电荷季铵基团和至少一个伯、仲或叔胺基团的聚胺阳离子化合物是非常好的表面活性剂，适用于清洗或洗涤剂组合物中。发现这些化合物在碱性洗涤条件下的表面活性非常好，并且发现它们提供了极好的清洗性能益处。人们相信：这是由于该化合物含有带正电荷的基团和中性的、更疏水的基团。
此外，发现这些表面活性剂的几个实例与大多数季铵化合物相比是更(容易)生物降解的并且具有非常低的水生毒性。
已经发现该聚胺阳离子表面活性剂的稳定性不受pH变化的影响，另外，已经发现：取决于其结构，本发明大部分的聚胺阳离子化合物和含有这些聚胺阳离子表面活性剂的洗涤剂组合物在标准储存和洗涤条件下是稳定的。
此外，还已经发现：该聚胺阳离子表面活性剂可以是与漂白剂，尤其是氧基漂白剂相容的，并且与某些漂白活化剂是相容的。
该聚胺阳离子表面活性剂可以通过各种有效的合成路线得到，并且这些化合物的生产是非常经济有效的。
在本发明说明书中引用的所有文献在相应部分均引入本文作为参考。
                     发明概述
本发明涉及含有至少一个季铵基团和至少一个伯、仲或叔胺基团的聚胺阳离子表面活性剂。本发明还涉及该聚胺阳离子表面活性剂的制备方法。本发明的该聚胺阳离子化合物可以在任何需要表面活性的组合物中，例如在清洗或洗涤剂组合物或其组分中用作表面活性剂。
                     发明详述
阳离子表面活性剂
根据本发明的阳离子表面活性剂包括至少一种季铵化的基团和至少一个伯、仲或叔胺基团，由此不多于1个直链或支链聚氧化烯基团是作为取代基存在的。
本发明的优选的阳离子表面活性剂是下面通式(I)的聚胺阳离子表面活性剂： 其中L是连接单元，并且每个L各自独立地选自C2-C30直链或支链亚烷基、亚烯基、亚烷芳基、亚芳烷基、亚芳基、(多)羟基亚烷基、(聚)亚烷氧基、(多)羟基亚烯基；L可以被一个或多个A、B、C或D单元取代；x是0-10的数，y是0-10的数；并且其中单元A-和D-各自独立地选自下面的基团：和
Figure A9880406000072
Figure A9880406000073
和其中R1、R2、R3、R4、R5、R6、R7和R8独立地选自C1-C30直链或支链烷基、链烯基、烷芳基、芳烷基、芳基、(多)羟基烷基、(多)羟基链烯基、烷氧基和氢，R1、R2、R3、R4、R5、R6、R7或R8之一可以是具有2-26个氧化烯单元的直链或支链聚氧化烯基团，或者R1和R2，R1和R2和R3，R4和R5或R6和R7与氮原子一起形成环结构的一部分；或者R3不存在并且R1或R2双键键合到该氮上；或者R7不存在并且R6双键键合到该氮上；或者R5不存在并且R4双键键合到该氮上；或者当x和y是0时，R1或R2或R3，和R4或R5与A和D的氮原子一起形成环结构的一部分；M-是一个或多个抗衡离子，并且至少一个A或D包括季铵基团，其中R1、R2或R3都不是氢，或者存在至少一个B，其中R6或R7都不是氢，和至少一个A或D包括伯、仲或叔胺基团，或者存在至少一个C。
当单元B-L和C-L都存在(即当x和y不等于0时)，它们是键连的，并且它们可以沿终端单元A-L和D之间的链无规地存在。
x+y的值优选是1-4。优选地，当x+y大于1时，存在的基团A、B、C或D的至少一个是伯或仲铵基团。
更优选地，x＝0并且y是1-4的数。更优选x和y都是0。
如果x+y不等于0，那么优选的是该表面活性剂仅包括一个季基团A或D。
R6、R7和/或R8优选各自独立地选自C1-C6，更优选C1-C3烷基、烷氧基烷基或(多)羟基烷基，或最优选氢。
R1优选是C6-C14烷基、(多)羟基烷基或烷氧基或芳烷基，最优选是2-乙基己基，R2和R3各自独立地是C1-C6，更优选C1-C3烷基或羟基烷基，和R4和R5(以及R6、R7和R8，当其存在时)优选各自独立地是C1-C6，更优选C1-C3烷基、烷氧基烷基或(多)羟基烷基，或最优选氢原子。
在另一个优选的方案中，R4优选是C6-C14烷基、(多)羟基烷基、烷氧基或芳烷基，最优选2-乙基己基，R5优选是C1-C6，更优选C1-C3烷基、(多)羟基烷基或氢，和R1、R2和R3(和R6、R7和R8，当其存在时)优选各自独立地是C1-C6，更优选C1-C3烷基、烷氧基烷基或(多)羟基烷基或芳烷基。
当R1和R2，R1和R2和R3，R4和R5或R6和R7与氮原子一起形成环结构的一部分时，该环结构优选是苯环结构、吗啉代环结构或哌嗪基环结构，或者取代的苯结构或取代的吗啉代结构或取代的哌嗪基环结构。
当x+y是0并且R1或R2或R3，和R4或R5与A和D的氮原子一起形成环结构的一部分时，该环结构优选是苯环结构、吗啉代环结构或哌嗪基环结构，或者取代的苯结构或取代的吗啉代结构或取代的哌嗪基环结构。
L基团优选独立地是C2-C8，更优选C2-C4直链或支链烷基、羟基烷基、烷氧基或羟基烷氧基。如果x+y是0，那么L基团优选是C2烷基。如果L基团包括多于2个碳原子的话，那么表面活性剂优选包括至少一个伯或仲的A、B、C或D基团。
本发明的优选的聚胺阳离子表面活性剂的例子是下面这些：
Figure A9880406000091
Figure A9880406000092
其中，R1、R4、R6和R8与上面所述的相同；R2、R3和R5独立地选自甲基、乙基、羟乙基、羟基丙基、多羟基丙基、乙氧基、丙氧基或2，3，4，5，6-五羟基己基，最优选是甲基或羟乙基；R10是甲基或羟乙基；L与上面所述的相同；R1和/或R2和/或R4最优选是2-乙基己基。
非常优选的阳离子聚胺表面活性剂是如上面所定义的式VI，其中R2是羟基丙基或羟基乙基，R3和R10是甲基，L是C2-C3烷基。
非常优选的聚胺阳离子表面活性剂是下式的这些：
Figure A9880406000102
或
Figure A9880406000103
其中R1与上面所述的相同，优选C2-C14，优选C6-C14直链或支链烷基、(多)羟基烷基、烷氧基或芳烷基；特别优选的R1是羟基烷基，其中该烷基具有2-5个碳原子，特别地，羟乙基和羟基丙基是优选的；特别优选的烷基R1基团具有最高达9个碳原子，最优选R1是2-乙基己基；R11是C2-C14烷基、(多)羟基烷基、烷氧基或芳烷基或如上所述的A或D单元。
阴离子M-是该带阳离子电荷的聚胺表面活性剂的抗衡离子。因此，M-阴离子存在的数取决于聚胺表面活性剂的阳离子电荷，其取决于基团A、B、C和D。M-阴离子的数至少是1。优选的抗衡离子是卤素阴离子，更优选硫酸根阴离子。
聚胺阳离子表面活性剂的合成
可以使用各种合成路线制备本发明的聚胺阳离子表面活性剂。取决于要制备的聚胺阳离子表面活性剂反应产物和可得到的原料，比起其它可能的合成路线来，一种合成路线是优选的，并且这种选择在本领域技术人员的知识范围内，下面给出实例。该原料可以选自各种可(容易)购得的化合物，这取决于要制备的聚胺阳离子表面活性剂的需要，这一选择也在本领域技术人员的知识范围内。该原料优选是胺或二胺化合物。
优选的合成路线(A-D)
A、2个含胺化合物的反应
优选的合成路线如下。在优选的有机溶剂中，优选以1.5∶1-3∶1的摩尔比将一个或多个伯或仲胺化合物和含卤化季盐或硫酸化季盐的胺化合物混合使其一起反应。当反应完成时，加入碱性化合物，优选氢氧化钠，并通过常规的方法可以从反应混合物中分离出聚胺阳离子表面活性剂反应产物。
该合成路线的例子是：在有机溶剂(乙醇)中，以约2∶1的比例，将己胺、辛胺、癸胺、十二烷胺或2-乙基己基胺的任一个与(3-溴代、氯代或硫酸盐丙基)三甲基铵的溴化物、氯化物或硫酸盐反应，之后加入氢氧化钠。当反应基本上完成时(反应高达24小时后)，通过蒸发从反应混合物中除去有机溶剂和可能未反应的胺化合物，并用(例如)二乙醚洗涤，从而得到白色的固体二胺阳离子表面活性剂，即(1-己基、辛基、癸基、十二烷基或2-乙基己基胺)(3-三甲基胺)丙烷。B、二胺的烷基化
另一个优选的合成路线如下。
在有机溶剂中将二胺化合物和烷基化试剂混合，优选该二胺与烷基化试剂的摩尔比是3.5∶1-1.1∶1。当反应完成时，可以通过常规的方法从反应混合物中分离出聚胺阳离子表面活性剂反应产物。
该合成路线的例子是：在有机溶剂(乙醇)中，将1-溴代或氯代己烷、辛烷、癸烷、十二烷或十四烷或2-乙基己基溴化物的任一个与四甲基丙二胺反应。反应物的摩尔比优选是约1∶1。当反应基本上完成时，通过蒸发从反应混合物中除去有机溶剂和任何未反应的胺化合物。然后用(例如)二乙醚洗涤剩余的产物，从而得到二胺阳离子表面活性剂，即己基、辛基、癸基、十二烷基、十四烷基、2-乙基己基、四甲基丙二胺。
C、亚胺的制备，还原和烷基化
再一个优选的合成路线如下。
在有机溶剂中，将醛化合物和二胺化合物以2∶1-1∶2的摩尔比混合，由此形成亚胺。将该亚胺反应产物用还原剂还原成仲二胺。然后用烷基化试剂例如甲醛/甲酸将该仲二胺产物在该仲胺上选择性地烷基化。然后使用烷基化试剂将该二胺季铵化/烷基化从而形成二胺阳离子表面活性剂。
该合成路线的例子是：在有机溶剂(甲苯)中，以约1∶1的摩尔比将2-乙基己醛、己醛、辛醛、癸醛或十二醛的任一个与N，N，二亚甲基二胺反应。当反应基本上完成时，除去溶剂并加入氢硼化物以便实现还原步骤。然后用甲酸和甲醛中和该还原的反应产物。然后将甲基溴化物/氯化物加入到该反应产物中从而得到白色的固体二胺阳离子表面活性剂，即N’-己基、辛基、癸基、十二烷基或乙基己基N，N，二甲基乙二胺。
D、二胺的选择烷基化
又一个优选的合成路线如下：
在有机溶剂中，将叔/伯烷基二胺和酐、酸、甲基酯或酰基氯反应，由此将伯胺基团酰化从而制备酰胺化合物。然后用烷基化试剂将该反应产物选择地烷基化，和用无机酸水解该酰胺产物从而制备二胺阳离子表面活性剂。
该合成路线的例子是：在有机溶剂(甲苯)中，将N，N二甲基乙二胺与乙酸酐反应，接着在有机溶剂(乙醇)中用溴代或氯代己烷、辛烷、癸烷或十二烷烷基化从而得到季铵酰胺。使用氢溴酸在水中将该反应产物水解从而制备二胺阳离子表面活性剂，即N，N，N，己基、辛基、癸基或十二烷基-二甲基乙二胺。
优选的聚胺阳离子表面活性剂的小规模合成实施例
                    实施例1
1.1
向250ml的装有回流冷凝器和干燥管的圆底烧瓶中放入在100ml乙醇中的1-溴代己烷(10.0g，0.061mol)和四甲基丙二胺(8.68g，0.067mol)。回流该混合物72小时。通过旋转蒸发除去乙醇，加入另外的乙醇以便除去未反应的胺。用二乙醚研制得到的粘性固体，而剩余的是糖浆。用270M Hz 1H NMR在CDCl3中分析得到下面峰值：δ0.9(t，4H)，1.3-1.5(bs)，1.7(m，2H)，1.95(m，2H)，2.25(s，6H)，2.4(t，2H)，3.4-3.7(2s，m，14H，包括乙醇)。
该合成也使用下面的原料进行：
1.2用其它烷基溴化物代替溴代己烷：
溴代辛烷          收率24％
溴代癸烷          收率14％
1.3用四甲基乙二胺代替四甲基丙二胺并使用下面的烷基溴化物：
烷基溴化物           收率
溴代己烷             85％
溴代辛烷             91％
溴代癸烷             85％
溴代十四烷           75％
2-乙基己基溴化物     88％
                  实施例2
2.1
向250ml的装有回流冷凝器和干燥管的圆底烧瓶中放入在100ml乙醇中的辛胺(7.50g，0.58mol)和(3-溴代丙基)三甲基溴化铵(10.15g，0.0387mol)。回流该混合物1天。再加入辛胺(2.50g，0.0193mol)，并回流该混合物1天。加入氢氧化钠(1.56g)并过滤该混合物以便除去所得的沉淀物。通过旋转蒸发除去乙醇，加入另外的乙醇以便除去未反应的胺。用二乙醚研制得到的粘性固体从而得到白色固体(10g，收率87.60％)。用270M Hz 1H NMR在CD3OD中分析得到下面峰值：δ0.9(t)，1.2-1.4(bs)，1.6(m)，2.0(m)，2.5-2.7(2m)，3.2(2s)，3.4(m)。
该合成也使用下面的原料进行：
2.2用下面的烷基胺代替辛胺。
    丁胺
    己胺
    癸胺
    十二烷基胺
    2-乙基己基胺
洗涤剂组合物和其组分
本发明的聚胺阳离子表面活性剂可用于任何需要表面活性的应用。例如，本发明的聚胺阳离子表面活性剂可用于洗涤剂组合物或其组分中。
取决于洗涤剂组合物或其组分的类型，本发明的聚胺阳离子表面活性剂可以以组合物或组分重量的0.05％-95％的含量存在。
洗涤剂组合物或其组分可以含有任何常规已知并用于洗涤剂的成分或组分。这些组分的确切性质和其加入量取决于组合物的物理形式和要使用其的洗涤操作的确切性质。
该洗涤剂组合物或其组分优选含有一种或多种洗涤剂组分，这些组分选自：附加的表面活性剂、漂白剂、漂白催化剂、漂白剂前体、水溶的和水不溶的助洗剂、螯合剂、有机聚合物、酶、抑泡剂、钙皂分散剂、污垢悬浮和抗再沉积剂、香料、增白剂和腐蚀抑制剂。
附加的表面活性剂可以选自阴离子、非离子、附加的阳离子、两性(ampholytic)、两性(amphoteric)和两性离子表面活性剂，和其混合物。
当其存在时，两性(ampholytic)、两性(amphoteric)和两性离子表面活性剂通常与一种或多种阴离子和/或非离子表面活性剂组合使用。洗涤剂组合物的pH
洗涤剂组合物作为1％去离子水溶液测定的pH优选至少是8.5，优选9.0-12.5，更优选9.5-11.0。
组合物的形式
包括本发明聚胺阳离子表面活性剂的洗涤剂或清洗组合物可以采用各种物理形式，包括粒状、片状、条状和液体形式。优选地，该组合物是所谓的浓缩粒状洗涤剂组合物，其适合于借助置于洗衣机转筒中的分配装置与脏织物负载一起入到洗衣机中。
通常，本发明的粒状洗涤剂组合物可以通过各种方法包括干混合、喷雾干燥、附聚和造粒来制备。

Claims (13)

1、一种阳离子表面活性剂，其包括至少一个季铵基团和至少一个伯、仲或叔胺基团，其中不多于1个直链或支链聚氧化烯基团是作为取代基存在的。
2、根据权利要求1的阳离子表面活性剂，其具有以下通式： 其中L是连接单元，并且每个L各自独立地选自C2-C30直链或支链亚烷基、亚烯基、亚烷芳基、亚芳烷基、亚芳基、(多)羟基亚烷基、(聚)亚烷氧基、(多)羟基亚烯基；L可以被一个或多个A、B、C或D单元取代；x是0-10的数，y是0-10的数；并且其中单元A-和D-各自独立地选自：
Figure A9880406000022
和
Figure A9880406000023
；和
Figure A9880406000025
其中R1、R2、R3、R4、R5、R6、R7和R8独立地选自C1-C30直链或支链烷基、链烯基、烷芳基、芳烷基、芳基、(多)羟基烷基、(多)羟基链烯基、烷氧基和氢，R1、R2、R3、R4、R5、R6、R7或R8之一可以是具有2-26个氧化烯单元的直链或支链聚氧化烯基团，或者R1和R2，R1和R2和R3，R4和R5或R6和R7与氮原子一起形成环结构的一部分；或者R3不存在并且R1或R2双键键合到该氮上；或者R7不存在并且R6双键键合到该氮上；或者R5不存在并且R4双键键合到该氮上；M-是一个或多个抗衡离子，并且至少一个A或D包括季铵基团，其中R1、R2或R3都不是氢，或者存在至少一个B，其中R6或R7都不是氢，和至少一个A或D包括伯、仲或叔胺基团，或者存在至少一个C。
3、根据权利要求2的聚胺阳离子表面活性剂，其中x＝0。
4、根据权利要求2的聚胺阳离子表面活性剂，其中x＝0和y＝0。
5、根据权利要求2-4任一项的聚胺阳离子表面活性剂，其中R1是C6-C14烷基。
6、根据权利要求2-5任一项的聚胺阳离子表面活性剂，其中R1或R4是2-乙基己基。
7、根据权利要求5的聚胺阳离子表面活性剂，其中R4和R5相互独立地是C1-C6烷基或(多)羟基烷基或氢原子。
8、根据权利要求5或7的聚胺阳离子表面活性剂，其中R4和R5是氢。
                (申请时未提供)
14、一种制备权利要求4-10任一项的聚胺阳离子表面活性剂的方法，其包括下面步骤：
(1)将二胺与酐反应从而形成酰化的二胺；
(2)将该酰化的二胺选择性地烷基化从而形成酰化和烷基化的二胺；和
(3)将该酰化烷基化的二胺水解从而形成根据权利要求4-10任一项的聚胺阳离子表面活性剂。
15、一种洗涤剂组合物或其组分，其含有根据权利要求1-10任一项的聚胺阳离子表面活性剂并含有一种或多种其它洗涤剂组分。
16、根据权利要求15的洗涤剂组合物，其中该洗涤剂组合物选自阴离子、非离子表面活性剂，水溶性和水不溶性的助洗剂及漂白剂。
17、制备权利要求15或16的洗涤剂组合物的方法，其包括将根据权利要求1-10任一项的聚胺阳离子表面活性剂与一种或多种其它洗涤剂组分混合。
18、根据权利要求17制备的洗涤剂组合物。
CN 98804060 1997-02-11 1998-02-11 洗涤剂化合物 Pending CN1252091A (zh)

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