CN117024291A - 烷氧基化酯胺及其盐 - Google Patents
烷氧基化酯胺及其盐 Download PDFInfo
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- CN117024291A CN117024291A CN202310957048.0A CN202310957048A CN117024291A CN 117024291 A CN117024291 A CN 117024291A CN 202310957048 A CN202310957048 A CN 202310957048A CN 117024291 A CN117024291 A CN 117024291A
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- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
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Abstract
本发明涉及式(I)的烷氧基化酯胺及其盐。根据本发明的酯胺可以用于清洁组合物,例如用于液体衣物洗涤剂。例如当在冷水洗涤条件下使用时,它们导致所述组合物的清洁性能改进。它们令人惊奇地提高了液体衣物洗涤剂的油脂清洁性能,尤其是在冷水洗涤条件下。还改进了白度。根据本发明的酯胺在液体衣物洗涤剂配制剂中显示出改进相容性。
Description
本申请是申请号为201880043926.5、申请日为2018年6月26日、发明名称为“烷氧基化酯胺及其盐”的专利申请的分案申请。
技术领域
本发明涉及烷氧基化酯胺及其盐。
背景技术
由于合成纤维制成的易护理织物的日益普及以及能源成本的增加和洗涤剂使用者日益关注的生态问题,曾经流行的热水洗涤现在已屈居于冷水洗涤织物。甚至许多市售衣物洗涤剂被宣传为适合在40℃或30℃下或甚至在室温下洗涤织物。为了在该类低温下获得令人满意的洗涤结果,即与使用热水洗涤所获得的那些相当的结果,对低温洗涤剂的要求特别高。
已知在洗涤剂组合物中包括某些添加剂来增强常规表面活性剂的洗涤能力,从而改善在60℃及更低的温度下油脂污渍的移除。
US6346643公开了一种制备聚乙二醇与氨基酸盐酸盐的酯的方法。
DE 2025629公开了谷氨酸和C10-C18脂肪醇的酯以及衍生物。
WO 2007/054226描述了焦谷氨酸酯作为气体水合物抑制剂的用途。焦谷氨酸酯通过焦谷氨酸或谷氨酸与包含1-100个羟基的醇的酯化获得。
JP2003064282公开了基于经C2-C21氨基酸酯化的三甘醇C1-C7单醚的半导体颗粒的配体。
JP2005263890公开了乙氧基化甘油的C6-C10ζ-至κ-氨基酸的酯。
WO2003059317描述了作为药用气溶胶组合物的一部分的经α-氨基酸酯化的聚乙二醇单甲基或乙基醚。
持续需要由织物和其他染污的物质移除油脂污渍的清洁组合物,因为油脂污渍为难以移除的污渍。用于油脂移除的常规清洁组合物通常使用各种胺化合物,该胺化合物往往对白度显示出强负面影响。结果,仍持续需要提供由织物和其他染污的物质移除油脂的能力且其同时不会负面影响粘土清洁能力或白度的胺化合物。需要在低温下具有油脂清洁能力的化合物。
发明内容
本发明的一个目的为提供符合上述目的和需要的化合物。
该目的通过如下文所述且如权利要求所反映的本发明实现。
在整个说明书和随后的权利要求书中,除非上下文另有要求,否则词语“包含(comprise)”以及变体如“包含(comprises)”和“包含(comprising)”将被理解为暗示包括所述整数或步骤或者整数或步骤的组,但不排除任何其他整数或步骤或整数或步骤的组。当在本文中使用时,术语“包含”可以用术语“含有”或“包括”替代,或者有时在本文中使用时用术语“具有”替代。
当在本文中使用时,“由...组成”排除权利要求要素中未指定的任何要素、步骤或成分。当在本文中使用时,“基本上由...组成”不排除不会实质性影响权利要求的基本和新特征的材料或步骤。
在本文的每种情况下,任何术语“包含”、“基本上由...组成”和“由...组成”可用其他两个术语中的任一个替代。
通常,如本文所用,术语“可通过……获得”是指相应产品不必须通过相应具体上下文中所述的相应方法或工艺过程来生产(即获得),而且还包括显现出通过所述相应方法或工艺过程生产(获得)的所有特征的产品,其中所述产品实际上并非通过该方法或工艺过程生产(获得)。然而,术语“可通过……获得”还包括更限制性的术语“通过……获得”,即实际上通过在相应具体上下文中所述的方法或工艺过程生产(获得)的产品。
本发明涉及式(I)的烷氧基化酯胺及其盐,
其中彼此独立地
t为1至100的整数;
A1对于每个重复单元t独立地选自由如下组成的列举:亚乙基氧基,1,2-亚丙基氧基,1,2-亚丁基氧基,2,3-亚丁基氧基,亚异丁基氧基,亚戊基氧基,亚己基氧基,苯乙烯基氧基,癸烯基氧基,十二碳烯基氧基,十四碳烯基氧基和十六碳烷基氧基,其中对于t等于1,基团A1的氧原子与基团B键合,且随后的基团A1总是通过氧原子与前面的基团A1键合;
B1独立地选自由如下组成的组:键,直链C1至C12烷二基和支化C1至C12烷二基;
R4、R8和R12选自由如下组成的组:H,直链烷基,支化烷基和环烷基;条件为Z1选自由如下组成的组:丙氨酸,精氨酸,天冬酰胺,天冬氨酸,半胱氨酸,谷氨酰胺,甘氨酸,组氨酸,异亮氨酸,亮氨酸,赖氨酸,蛋氨酸,苯丙氨酸,脯氨酸,丝氨酸,苏氨酸,色氨酸,酪氨酸,缬氨酸和根据式(II)的化合物,其中所述根据式(II)的化合物通过标记有*的键与根据式(I)的化合物连接,条件为至少一个基团R4、R8和/或R12包含至少7个或更多个碳原子;
其中彼此独立地
w为0至12的整数;
R13和R14对于每个重复单元w独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基;
R15、R16、R17和R18选自由如下组成的组:H,直链烷基,支化烷基和环烷基。
根据本发明的酯胺可以用于清洁组合物,例如液体衣物洗涤剂。例如当在冷水洗涤条件下使用时,它们导致所述组合物的清洁性能的改善。它们令人惊奇地提高了液体衣物洗涤剂的油脂清洁性能,尤其是在冷水洗涤条件下。根据本发明的酯胺在液体衣物洗涤剂配制剂中显示出改善的相容性。
具体实施方式
在下文中更详细地描述本发明的各种实施方案:
A1对于每个重复单元t独立地选自由如下组成的列举:亚乙基氧基,1,2-亚丙基氧基,1,2-亚丁基氧基,2,3-亚丁基氧基,亚异丁基氧基,戊烯基氧基,己氧基,苯乙烯基氧基,癸烯基氧基,十二碳烷基氧基,十四碳烯基氧基和十六碳烯基氧基,其中对于t等于1,基团A1的氧原子与基团B键合,且随后的基团A1总是通过氧原子与前面的基团A1键合。当t等于或大于2时,对每个重复单元t独立选择的A1形成各种亚烷基氧基(alkylenyloxy)单元的随机分布的侧链,或形成本身重复至少两次的具有至少一个亚烷基氧基的嵌段结构(任选地随后为本身重复至少两次的不同亚烷基氧基的其他嵌段)。
在一个实施方案中,A1对于每个重复单元t独立地选自由如下组成的列举:亚乙基氧基,1,2-亚丙基氧基,1,2-1,2-亚丙基氧基和1,2-亚丁基氧基。在另一实施方案中,A1形成至少两个亚乙基氧基的嵌段和随后的至少两个亚丙基氧基的嵌段以及任选地随后的至少两个亚乙基氧基的另外嵌段。在另一实施方案中,A1形成至少两个1,2-亚丙基氧基的嵌段和随后的至少两个亚乙基氧基的嵌段以及任选地随后的至少两个1,2-亚丙基氧基的另外嵌段。在另一实施方案中,A1选自由如下组成的列举:亚乙基氧基,1,2-亚丙基氧基和1,2-亚丁基氧基,使得形成至少一个亚乙基氧基、1,2-亚丙基氧基或1,2-亚丁基氧基的嵌段以及任选地随后的一个或多个亚乙基氧基、1,2-亚丙基氧基或1,2-亚丁基氧基的嵌段。在另一实施方案中,A1为亚乙基氧基。在另一实施方案中,A1为1,2-亚丙基氧基。在另一实施方案中,A1以使得1-5个亚乙基氧基的嵌段随后为1-3个亚丙基氧基的嵌段以及随后的1-5个亚乙基氧基的嵌段的方式选择。
在一个实施方案中,t为1-50。在另一实施方案中,t为1-20。在另一实施方案中,t为2-10。
在本发明的一个实施方案中,B1选自由如下组成的组:键和直链C1至C12烷二基。在另一实施方案中,B1选自由如下组成的组:键和直链C1至C6烷二基。在另一实施方案中,B1选自由如下组成的组:键和直链C1至C3烷二基。在另一实施方案中,B1选自由如下组成的组:键和C1烷二基。在另一实施方案中,B1选自由如下组成的组:键和C1烷二基。在另一实施方案中,B1为键。
在本发明的一个实施方案中,R4、R8和R12均独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基。在一个实施方案中,R4、R8和R12均独立地选自由如下组成的组:H,直链C1至C12烷基和支化C1至C12烷基。在另一实施方案中,R4、R8和R12均独立地选自由如下组成的组:H,直链C1至C6烷基和支化C1至C9烷基。
对于Z1选择根据式(II)的化合物,所述根据式(II)的化合物通过标记有*的键与式(I)的化合物连接,
其中彼此独立地
w为0至12的整数;
R13和R14对于每个重复单元w独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基;
R15、R16、R17和R18选自由如下组成的组:H,直链烷基,支化烷基和环烷基。在本发明的一个实施方案中,R13、R14、R15、R16、R17和R18均独立地选自由如下组成的组:H,直链C1至C12烷基和支化C1至C12烷基。在另一实施方案中,R13、R14、R15、R16、R17和R18均独立地选自由如下组成的组:H,直链C1至C6烷基和支化C1至C9烷基。
在本发明的一个实施方案中,Z1选自由如下组成的组:丙氨酸,甘氨酸,赖氨酸和其中w为1-4的整数的根据式(II)的化合物,且根据式(II)的化合物通过标记有*的键与根据式(I)的化合物连接,条件为至少一个基团R4、R8和/或R12包含至少7个或更多个碳原子。在另一实施方案中,Z1为丙氨酸。在另一实施方案中,Z1为w=0和R15至R18均为H的根据式(II)的化合物。在另一实施方案中,Z1为w=1和R13至R18均为H的根据式(II)的化合物。在另一实施方案中,Z1为w=3和R13至R18均为H的根据式(II)的化合物。
在本发明的另一实施方案中,B1选自支化或直链C1至C12烷基且R8选自直链或支化C6至C23烷基。在本发明的另一实施方案中,B1选自支化或直链C1至C12烷基且R8选自直链或支化C1至C3烷基。另一实施方案由如下组成:B1为2-乙基乙烷二基和R8为直链C3烷基。
在本发明的另一实施方案中,B1选自支化或直链C1至C12烷基且R8选自直链或支化C1至C3烷基,且Z1为w=3和R13至R18均为H的根据式(II)的化合物。
在本发明的另一实施方案中,B1选自支化或直链C6至C12烷基且R8选自直链或支化C1至C3烷基,t为1-10,A1对于每个重复单元t为亚乙基氧基,且Z1选自由如下组成的组:丙氨酸,其中w=0和R15至R18均为H的根据式(II)的化合物,其中w=1和R13至R18均为H的根据式(II)的化合物以及其中w=3和R13至R18均为H的根据式(II)的化合物。
在本发明的另一实施方案中,B1选自支化或直链C6至C12烷基且R8选自直链或支化C1至C3烷基,R4和R12选自H和直链或支化C1-C3烷基,t为1-10,A1对于每个重复单元t为1,2-亚丙基氧基,且Z1选自由如下组成的组:丙氨酸,其中w=0和R15至R18均为H的根据式(II)的化合物,其中w=1和R13至R18均为H的根据式(II)的化合物以及其中w=3和R13至R18均为H的根据式(II)的化合物。
根据本发明的酯胺以游离胺、其盐或游离胺和盐的混合物形式获得。盐通过用作为质子性有机酸或质子性无机酸的酸使胺基团至少部分质子化而形成。在一个实施方案中,用于使胺基团至少部分质子化的酸选自由如下组成的组:甲磺酸,盐酸,氢溴酸,硫酸,磷酸,柠檬酸和乳酸。在一个实施方案中,该酸选自甲磺酸、盐酸和硫酸的组。在另一实施方案中,该酸为甲磺酸。
部分质子化在一个实施方案中为所有胺基团的1-99mol%,在另一实施方案中为所有胺基团的10-90mol%,在另一实施方案中为所有胺基团的25-85mol%,在另一实施方案中为所有胺基团的40-75mol%范围内的胺基团的质子化。
本发明还包括至少两个如本文所述的实施方案的组合。
本发明还涉及制备酯胺或其盐的方法,其包括以下步骤:
a)用一种或多种C2-C16氧化烯使根据式(III)的醇烷氧基化:
其中彼此独立地
B1彼此独立地选自由如下组成的组:键,直链C1至C12烷二基和支化C1至C12烷二基;
R4、R8和R12选自由如下组成的组:H,直链烷基,支化烷基和环烷基;b)用至少一种选自由如下组成的组的酸使烷氧基化醇至少部分酯化:丙氨酸,精氨酸,天冬酰胺,天冬氨酸,半胱氨酸,谷氨酰胺,甘氨酸,组氨酸,异亮氨酸,亮氨酸,赖氨酸,蛋氨酸,苯丙氨酸,脯氨酸,丝氨酸,苏氨酸,色氨酸,酪氨酸,缬氨酸和式(IV)的酸,
其中w为0至12的整数;
R13和R14对于每个重复单元w独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基;
R15、R16、R17和R18选自由如下组成的组:H,直链烷基,支化烷基和环烷基。
在本发明的一个实施方案中,B1选自由如下组成的组:键和直链C1至C12烷二基。在另一实施方案中,B1选自由如下组成的组:键和直链C1至C6烷二基。在另一实施方案中,B1选自由如下组成的组:键和直链C1至C3烷二基。在另一实施方案中,B1选自由如下组成的组:键和C1烷二基。在另一实施方案中,B1为键。
在本发明的一个实施方案中,R4、R8和R12均独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基。在一个实施方案中,R4、R8和R12均独立地选自由如下组成的组:H,直链C1至C12烷基和支化C1至C12烷基。在另一实施方案中,R4、R8和R12均独立地选自由如下组成的组:H,直链C1至C6烷基和支化C1至C9烷基。
步骤a)用至少一种C2-C16氧化烯使根据式(III)的醇烷氧基化
可使式(III)的醇与一种单C2至C16氧化烯或两种或更多种不同的C2至C16氧化烯的组合反应。使用两种或更多种不同的C2至C16氧化烯,可以以嵌段结构或无规结构获得所得聚合物。
式(III)的醇与总氧化烯的摩尔比可以为1:1至1:400。在一个实施方案中,式(III)的醇的羟基的摩尔数与用其进行烷氧基化反应的氧化烯的摩尔比可以为1:1至1:100。在另一实施方案中,式(III)的醇的羟基的摩尔数与用其进行烷氧基化反应的氧化烯的比例可以为1:2至1:50,在另一实施方案中为1:3至1:10。
该反应通常可以在催化剂存在下在约70至约200℃,在另一实施方案中约80至约160℃的反应温度下进行。该反应可以在至多约10巴的压力下进行,在另一实施方案中在至多约8巴的压力下进行。
合适催化剂的实例包括碱性催化剂如碱金属和碱土金属氢氧化物,例如氢氧化钠、氢氧化钾和氢氧化钙,碱金属醇盐,尤其是钠和钾的C1-C4醇盐,例如甲醇钠、乙醇钠和叔丁醇钾,碱金属和碱土金属氢化物如氢化钠和氢化钙以及碱金属碳酸盐如碳酸钠和碳酸钾。在一个实施方案中,使用碱金属氢氧化物。在另一实施方案中,使用氢氧化钾和氢氧化钠。基于醇和C2至C16氧化烯的总量,碱的典型用量为0.01-10重量%,尤其是0.05-2重量%。
步骤b)酯化
酯化反应可以如本领域中所已知的进行。可以将无机或有机质子酸加入步骤a)的产物。氨基酸与步骤a)的烷氧基化醇的羟基的摩尔比为0.8:1至1:1.5。在一个实施方案中,该方法以0.1:1至1:1的酸与步骤a)的烷氧基化醇的羟基的摩尔比进行。反应温度可以为50-200℃,在另一实施方案中为80-160℃。反应可以通过施加1000毫巴至1毫巴,在另一实施方案中500毫巴至5毫巴的真空进行。反应时间可为2-48小时。适用于该反应的溶剂可以为水、甲苯、二甲苯。
如本文所述和所示例的洗衣效果可以外推至个人护理应用。
酯胺及其盐可用于个人护理中、作为环氧树脂的固化剂,作为聚合物生产中的反应物、在聚氨酯、聚脲中或作为热塑性聚酰胺粘合剂中的应用。还可以用于洗发水或洁身配制剂中。酯胺及其盐可以包括于个人护理组合物中。
方法
1H NMR用Bruker Avance 400MHz光谱仪在MeOD中测量。
pH在10%水溶液中测量。
羟值根据DIN 53240-1测量。
聚氧化烯(例如聚乙二醇)的分子量由所测得的羟值通过下式计算出:
分子量[g/mol]=1000/(羟值[mgKOH/g]/56.11)x每分子的羟基数
实施例
实施例1:经3摩尔氧化乙烯乙氧基化的2-丙基庚醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入58.1g用3摩尔氧化乙烯乙氧基化的2-丙基庚醇和26.2g 6-氨基己酸并加热至90℃。在10分钟内向该混合物中加入19.6g甲磺酸。将反应混合物加热至130℃,并在130℃下搅拌0.5小时。施加真空(2毫巴),并将反应混合物在130℃下再搅拌10小时。得到90.5g浅棕色固体。在MeOD中的1H-NMR表明完全转化为甲磺酸盐形式的6-氨基己酸-三甘醇2-丙基庚基醚酯。
实施例2:经3摩尔氧化乙烯乙氧基化的C13羰基合成醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入65.93g用3摩尔氧化乙烯乙氧基化的C13羰基合成醇和26.23g 6-氨基己酸并加热至90℃。在10分钟内向该混合物中加入19.6g甲磺酸。将反应混合物加热至135℃,并在135℃下搅拌7.0小时。施加真空(5毫巴),并将反应混合物在130℃下再搅拌3小时。得到101.95g浅棕色固体。在MeOD中的1H-NMR表明完全转化为甲磺酸盐形式的6-氨基己酸-三甘醇C13羰基合成醇酯。
实施例3:
3a:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的C12/C14脂肪醇
在2升高压釜中放入573.6g C12/C14脂肪醇和2.4g叔丁醇钾,并将混合物加热至140℃。用氮气吹扫容器三次,并在5小时内加入348.5g氧化丙烯。将混合物再搅拌6小时,然后在5小时内加入264.3g氧化乙烯。为了完成反应,使混合物在140℃下再后反应6小时。用氮气汽提反应混合物,并在80℃下真空移除挥发性化合物。在过滤后,获得1178.0g浅黄色油(羟基值:141.8mgKOH/g)。
3b:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的C12/C14脂肪醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入59.3g经2mol氧化丙烯和2mol氧化乙烯烷氧基化的C12/C14脂肪醇和17.9g 6-氨基己酸并加热至90℃。在10分钟内向该混合物中加入13.4g甲磺酸。在加料期间使温度升至70℃。将反应混合物加热至130℃,并在130℃下搅拌13小时。在升高的温度(135℃)下真空(2毫巴)移除挥发性化合物,并得到81.0g浅棕色固体。在MeOD中的1H-NMR表明完全转化为经2mol氧化丙烯和2mol氧化乙烯烷氧基化的C12/C14脂肪醇与6-氨基己酸的酯的甲磺酸盐。
实施例4:
4a:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-乙基己醇
在2升高压釜中放入390.7g 2-乙基己醇和2.0g叔丁醇钾,并将混合物加热至140℃。用氮气吹扫容器三次,并在4小时内加入348.5g氧化丙烯。将混合物再搅拌6小时,然后在3小时内加入264.3g氧化乙烯。为了完成反应,使混合物在140℃下再后反应6小时。用氮气汽提反应混合物,并在80℃下真空移除挥发性化合物。获得1024.0g浅黄色油(羟基值:164.0mgKOH/g)。
4b:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-乙基己醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入50.2g经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-乙基己醇和17.9g 6-氨基己酸并加热至60℃。在10分钟内向该混合物中加入13.4g甲磺酸。在加料期间使温度升至70℃。将反应混合物加热至130℃,并在130℃下搅拌13小时。在升高的温度(135℃)下真空(2毫巴)移除挥发性化合物,并得到72.0g浅棕色固体。在MeOD中的1H-NMR表明完全转化为经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-乙基己醇与6-氨基己酸的酯的甲磺酸盐。
实施例5:
5a:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-丙基庚醇
在2升高压釜中放入474.0g 2-丙基庚醇和2.4g叔丁醇钾,并将混合物加热至140℃。用氮气吹扫容器三次,并在4小时内加入348.5g氧化丙烯。将混合物再搅拌6小时,然后在3小时内加入264.3g氧化乙烯。为了完成反应,使混合物在140℃下再后反应6小时。用氮气汽提反应混合物,并在80℃下真空移除挥发性化合物。获得1065.0g浅黄色油(羟基值:152.0mgKOH/g)。
5b:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-丙基庚醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入59.8g经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-丙基庚醇和19.7g 6-氨基己酸并加热至60℃。在10分钟内向该混合物中加入14.7g甲磺酸。在加料期间使温度升至70℃。将反应混合物加热至130℃,并在130℃下搅拌5小时。然后,施加真空(800毫巴)并将混合物在这些条件下搅拌2小时。在升高的温度(140℃)下真空(2毫巴)移除挥发性化合物,并得到86.9g浅棕色固体。在MeOD中的1H-NMR表明完全转化为经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-丙基庚醇与6-氨基己酸的酯的甲磺酸盐。
实施例6:
6a:经1mol氧化乙烯乙氧基化的2-乙基己醇
在2升高压釜中放入651.1g 2-乙基己醇和1.74g叔丁醇钾,并将混合物加热至140℃。用氮气吹扫容器三次,并在4小时内加入220.3g氧化乙烯。为了完成反应,使混合物在140℃下再搅拌5小时。用氮气汽提反应混合物,并在80℃下真空移除挥发性化合物。获得870.0g浅黄色油(羟基值:321.0mgKOH/g)。
6b:经1mol氧化乙烯乙氧基化的2-乙基己醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入38.3g经1mol氧化乙烯乙氧基化的2-乙基己醇和26.2g 6-氨基己酸并加热至60℃。在10分钟内向该混合物中加入19.6g甲磺酸。在加料期间使温度升至70℃。将反应混合物加热至130℃,并在130℃下搅拌4小时。施加真空并在升高的温度(135℃)下真空(5毫巴)移除挥发性化合物。得到72.0g浅棕色固体。在MeOD中的1H-NMR表明完全转化为经1mol氧化乙烯乙氧基化的2-乙基己醇与6-氨基己酸的酯的甲磺酸盐。
实施例7:
7a:经1mol氧化乙烯乙氧基化的2-丙基庚醇
在2升高压釜中放入794.0g 2-丙基庚醇和2.0g叔丁醇钾,并将混合物加热至140℃。用氮气吹扫容器三次,并在4小时内加入220.9g氧化乙烯。为了完成反应,使混合物在140℃下再搅拌5小时。用氮气汽提反应混合物,并在65℃下真空移除挥发性化合物。获得1010.0g浅黄色油(羟基值:275.0mgKOH/g)。
7b:经1mol氧化乙烯乙氧基化的2-丙基庚醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入44.5g经1mol氧化乙烯乙氧基化的2-丙基庚醇和26.2g 6-氨基己酸并加热至60℃。在10分钟内向该混合物中加入19.6g甲磺酸。在加料期间使温度升至70℃。将反应混合物加热至130℃,并在130℃下搅拌4小时。施加真空并在升高的温度(135℃)下真空(4毫巴)移除挥发性化合物。得到80.0g浅棕色固体。在MeOD中的1H-NMR表明完全转化为经1mol氧化乙烯乙氧基化的2-丙基庚醇与6-氨基己酸的酯的甲磺酸盐。
对比例1:丁基三甘醇醚与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入64.39g丁基三甘醇醚和39.35g 6-氨基己酸并加热至90℃。在10分钟内向混合物中加入29.4g甲磺酸。将反应混合物加热至135℃,并在135℃下搅拌4小时。施加真空(5毫巴),并将反应混合物在130℃下再搅拌13.5小时。得到122.0g浅棕色固体。在MeOD中的1H-NMR表明完全转化为甲磺酸盐形式的6-氨基己酸-丁基三甘醇酯。
对比例2:Mw为约200g/mol的聚乙二醇与6-氨基己酸的酯的甲磺酸盐
在具有温度计、回流冷凝器、氮气入口、滴液漏斗和搅拌器的4颈烧瓶中放入30.0g聚乙二醇(Mw为约200g/mol)和39.35g 6-氨基己酸并加热至90℃。在10分钟内向混合物中加入29.4g甲磺酸。将反应混合物加热至135℃,并在135℃下搅拌4小时。施加真空(5毫巴),并将反应混合物在135℃下再搅拌22小时。得到97.0g浅棕色固体。在MeOD中的1H-NMR表明完全转化为甲磺酸盐形式的6-氨基己酸-聚乙二醇酯。
实施例8作为在洗涤剂中的添加剂的用途
包含咸肉油脂(Bacon Grease)的蓝色针织棉的技术性污渍色样购自WarwickEquest Ltd.。在室温下使用每罐500mL洗涤溶液,20个金属球和压载物织物,在launder-o-meter(由SDL Atlas制造)中将污渍洗涤30分钟。该洗涤溶液包含5000ppm洗涤剂组合物DC1(表1)。水硬度为2.5mM(Ca2+:Mg2+为4:1)。将添加剂以如下详述的量分别加入各罐的洗涤溶液中。在加料后,将pH值再调节至不含添加剂的洗涤溶液的pH值。
在洗涤前后,使用标准比色法测量获得各污渍的L*、a*和b*值。由L*、a*和b*值,以污渍和未处理的织物之间的色差ΔE(根据DIN EN ISO 11664-4计算)计算污渍水平。
由样品移除的污渍的计算如下:
ΔE初始=洗涤前的污渍水平
ΔE洗涤后=洗涤后的污渍水平
污渍水平对应于织物上的油脂量。洗涤前的织物污渍水平(ΔE初始)高,在洗涤过程中,移除污渍,且洗涤后的污渍水平(ΔE洗涤后)较小。移除污渍越好,ΔE洗涤后的值越小,差也就越接近ΔE初始。因此,除污指数的值会随着洗涤性能的提高而增加。
表1:洗涤剂组合物DC1
表2:使用实施例2的洗涤实验
表3:使用实施例5b的洗涤实验:经2mol氧化丙烯和2mol氧化乙烯烷氧基化的2-丙基庚醇与6-氨基己酸的酯的甲磺酸盐
作为在洗涤剂中的添加剂的用途
使用来自wfk Testgewebe GmbH的技术性污渍wfk20D(聚酯/棉65/35,污染物:颜料/皮脂)。如上所述但使用1584ppm的洗涤剂组合物2(表4)进行洗涤程序和除污指数的测定。在使用和不使用添加剂洗涤之前,在每种情况下将洗涤溶液的pH调节至pH=8.0。
表4:洗涤剂组合物DC2
液体洗涤剂组合物DC2的成分 | 重量百分比 |
直链C11.8-烷基苯磺酸 | 17,6 |
C12-C15烷基乙氧基(1.8)硫酸盐 | 4.4 |
C12-C14醇+9氧化乙烯 | 0.9 |
C12-C18脂肪酸 | 1.1 |
C12-C14氧化胺 | 0.8 |
螯合剂 | 2.8 |
溶剂 | 14.8 |
增白剂 | 0.2 |
氢氧化钠 | 1.9 |
水 | 余量 |
Claims (13)
1.式(I)的酯胺的盐:
其中彼此独立地
t为1至20的整数;
A1对于每个重复单元t独立地选自由如下组成的列举:亚乙基氧基,1,2-亚丙基氧基,1,2-亚丁基氧基,2,3-亚丁基氧基,亚异丁基氧基,亚戊基氧基,亚己基氧基,苯乙烯基氧基,癸烯基氧基,十二碳烯基氧基,十四碳烯基氧基和十六碳烷基氧基,其中对于t等于1,基团A1的氧原子与基团B键合,且随后的基团A1总是通过氧原子与前面的基团A1键合;
B1独立地选自由如下组成的组:键,直链C1至C12烷二基和支化C1至C12烷二基;
R4、R8和R12选自由如下组成的组:H,直链烷基,支化烷基和环烷基;条件为Z1选自由如下组成的组:丙氨酸,精氨酸,天冬酰胺,半胱氨酸,谷氨酰胺,甘氨酸,组氨酸,异亮氨酸,亮氨酸,赖氨酸,蛋氨酸,苯丙氨酸,脯氨酸,丝氨酸,苏氨酸,色氨酸,酪氨酸,缬氨酸和根据式(II)的化合物,其中所述根据式(II)的化合物通过标记有*的键与根据式(I)的化合物连接,条件为至少一个基团R4、R8和/或R12包含至少7个或更多个碳原子;
其中彼此独立地
w为0至12的整数;
R13和R14对于每个重复单元w独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基;
R15、R16、R17和R18选自由如下组成的组:H,直链烷基,支化烷基和环烷基,
其中该盐通过由作为质子性有机酸或无机酸的酸使胺基团至少部分质子化而形成。
2.根据权利要求1的酯胺的盐,其中该盐通过选自由如下组成的组的酸使胺基团至少部分质子化而形成:甲磺酸,盐酸,氢溴酸,硫酸,磷酸,柠檬酸和乳酸。
3.根据前述权利要求中任一项的酯胺的盐,其中A1对于每个重复单元t独立地选自由如下组成的列举:亚乙基氧基,1,2-亚丙基氧基和1,2-亚丁基氧基。
4.根据前述权利要求中任一项的酯胺的盐,其中Z1选自由如下组成的组:丙氨酸,甘氨酸,赖氨酸和其中w为1-4的整数的根据式(II)的化合物,其中根据式(II)的化合物通过标记有*的键与根据式(I)的化合物连接,条件为至少一个基团R4、R8和/或R12包含至少7个或更多个碳原子。
5.制备根据权利要求1的酯胺的盐的方法,其包括以下步骤:
a)使根据式(III)的醇与一种或多种C2-C16氧化烯反应:
其中彼此独立地
B1彼此独立地选自由如下组成的组:键,直链C1至C12烷二基和支化C1至C12烷二基;
R4、R8和R12选自由如下组成的组:H,直链烷基,支化烷基和环烷基;然后
b)用至少一种选自由如下组成的组的化合物至少部分酯化烷氧基化醇:丙氨酸,精氨酸,天冬酰胺,半胱氨酸,谷氨酰胺,甘氨酸,组氨酸,异亮氨酸,亮氨酸,赖氨酸,蛋氨酸,苯丙氨酸,脯氨酸,丝氨酸,苏氨酸,色氨酸,酪氨酸,缬氨酸、根据式(IV)的酸及其盐,
其中w为0至12的整数;
R13和R14对于每个重复单元w独立地选自由如下组成的组:H,直链烷基,支化烷基和环烷基;
R15、R16、R17和R18选自由如下组成的组:H,直链烷基,支化烷基和环烷基。
6.根据权利要求5的方法,其中根据式(III)的醇与总C2-C12氧化烯的摩尔比为1:1至1:400。
7.根据权利要求5或6的方法,其中酸与烷氧基化醇的羟基的摩尔比为0.1:1至1:1。
8.根据权利要求1-4的酯胺的盐在洗涤剂中的用途。
9.根据权利要求8的酯胺的盐的用途,其中所述酯胺的盐用于液体洗涤剂。
10.根据权利要求9的用途,其中所述酯胺的盐用于液体衣物洗涤剂。
11.一种洗涤剂组合物,包含根据权利要求1-5中任一项的酯胺的盐。
12.根据权利要求11的洗涤剂组合物,其为液体形式。
13.根据权利要求12的洗涤剂组合物,其为液体衣物洗涤剂。
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