CN105339345A - 作为水凝胶化添加剂的基于己内酰胺的脂肪酰胺 - Google Patents
作为水凝胶化添加剂的基于己内酰胺的脂肪酰胺 Download PDFInfo
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Abstract
本发明涉及基于脂肪酰胺的水凝胶化添加剂,其由脂肪酸R1CO2H在己内酰胺上的加成反应制得,该产物携带酸形式或通过中和剂成盐的形式的末端羧酸官能团,且所述添加剂由以下物质组成或含有以下物质:三种不同酰胺化合物的混合物,其得自所述反应,且特征在于引入的己内酰胺单元的数量n,该数量n分别是1、2和3,其中单元的平均数量n(每分子平均)为0.8-3。本发明还涉及含有所述添加剂的含水组合物,特别是用于涂料、胶、粘合剂或化妆品或用于处理纤维或纺织品或用于清洁剂或剥离剂、或污染去除剂或絮凝剂的含水组合物,例如该添加剂作为水凝胶化试剂的用途。
Description
本发明涉及携带羧酸端部或为盐形式的脂肪酰胺添加剂,其用作用于含水组合物的水凝胶因子(水胶凝剂,hydrogelator),特别是用于涂料(涂层,coating)或粘合剂,或纤维或纺织品的处理,或用于清洁剂、剥离剂、去污染剂(depollutingagents)或絮凝剂的水凝胶因子。
可在水中凝胶的多种系统是已知的并在多种应用中使用。
FR2976948描述了硼的酸(例如硼酸)、与N-烷基醛糖酰胺(特别是N-十二烷基-D-葡糖酰胺(glucoanamide))和单价盐(例如NaCl)的三元组合,以便得到用于多种应用且特别是用于去垢的在(含盐的)水介质中的凝胶。
已知的水凝胶因子包括基于赖氨酸的衍生物的那些,如M.Suzuki等在Chem.Soc.Rev.,2009,38,967-975中所描述的,其中还描述了用作有机凝胶因子(organogelators)的衍生物。在这些衍生物中,给出了始自赖氨酸的二脲-酯、二酰胺-酯或酰胺-脲-酯的描述。
L.A.Estroff等在ChemicalReviews,2004,104,3,1201-1217中对水性凝胶因子进行了品论,其中对已知的特征方法和结构进行了盘点。在其中特别挑出了具有亲水性头部和一个或两个憎水性链的传统两亲性衍生物、具有通过憎水性链键合的两个亲水性头部的哑铃型两亲物(bolaamphiphiles)、具有由具有两个柔性端链的刚性间隔物(rigidspacer)分开的双离子性头部的表面活性剂、衍生自糖的体系。人们认识到不存在使得可发现在分子的亲水性和憎水性之间令人满意的折衷的可适用的通用规则,因此也不存在在水介质中形成凝胶的能力和防止纤维沉淀的趋势之间的通用规则。
这些水性凝胶因子的缺点是这样的事实:它们基于氨基酸,所述氨基酸根据制备所述凝胶因子的条件可经历副反应且特别是不受控的链增长,和由此可影响它们的精细结构和因此它们的凝胶因子性能。更进一步地,引用的文件中都没有形容或教导如何获得通过己内酰胺改性的且具有改进的性能的酰胺添加剂,这是本发明的主题以克服现有技术中缺点。
具体而言,本发明试图开发通过己内酰胺(等价于C6氨基酸)改性的新型酰胺添加剂,而不必依靠与自身缩合的氨基酸或通过缩聚反应且具有待除去的副产物的酸和胺。这些经改性的酰胺使得可在己内酰胺受控的开环的情况下使用简单且对于实施而言实用的制备方法,以便避免在使用等价的氨基酸且难以避免的副反应并且不需要最终产物的分离和/或纯化的阶段,这展现出令人满意的在水介质中的流变性能,而不影响针对于可与其联合使用的含水粘结剂的性能。
本发明的第一主题是基于脂肪酰胺的水性凝胶因子添加剂,该添加剂是脂肪酸R1CO2H与己内酰胺加成反应的产物(没有副产物,如缩聚反应中的)并(其产物)带有酸形式或通过中和剂成盐的形式的末端羧基官能团,所述添加剂由以下物质组成或含有以下物质:3种不同酰胺化合物的混合物,所述3种不同酰胺化合物得自所述反应且特征在于引入的己内酰胺单元的数量n,该数量分别为1、2和3,其中单元的平均数量n(每分子平均)为0.8-3、优选0.9-2.75和更优选0.9-2.5。更具体地,所述三种化合物可根据下列式(I)定义,并且分别对应于n=1、n=2和n=3:
R1-C(=O)-[NH(CH2)5C(=O)-]n-1-NH(CH2)5-CO2M(I)
其中M为-H或在所述成盐形式的情况下为阳离子,所述阳离子与所述中和剂相关。
所述脂肪酸R1CO2H含有10-24的碳原子数,其意味着R1是含9-23个碳原子的烷基,其优选为直链的烷基。
作为R1CO2H的合适的例子,可提及脂肪一元酸,例如癸酸至十一烷酸、十二烷或月桂酸、十三烷酸、十四烷(或肉豆蔻)酸、十五烷酸、十六烷酸(棕榈酸)、十七烷酸、十八烷酸(硬脂酸)或它们的异构体和它们的混合物。
脂肪酸R1CO2H还可在其结构中含有烯属不饱和度,如在使用油酸(9-十八烯酸)的情况下。
R1CO2H可在其结构中含有羟基官能团,也就是说可以是脂肪羟基酸,例如12-羟基硬脂酸、9-羟基硬脂酸和/或10-羟基硬脂酸或14-羟基二十烷酸,优选单独的12-羟基硬脂酸或由9-羟基硬脂酸和/或10-羟基硬脂酸或14-羟基二十烷酸部分替代的12-羟基硬脂酸。R1CO2H可同时含有烯属不饱和度和OH官能团,例如,蓖麻油酸(或12-羟基-9-十八碳烯酸)或14-羟基二十碳烯酸。优选地,所述脂肪酸R1CO2H不包括任何羟基(OH)或胺官能团或其它可与己内酰胺反应的官能团,以避免任何潜在的副反应并更好地控制根据本发明的所述酰胺添加剂的最终结构和组成。
根据可能的选择,所述酰胺添加剂为成盐的形式(羧酸盐的形式)并且所述中和剂选自有机或无机碱。作为有机碱的实例,可提及伯胺、仲胺和叔胺,优选叔胺,以形成为季铵的阳离子M,对阴离子为通过酰胺链携带的羧酸根。作为无机碱,可提及碱金属氢氧化物,例如LiOH、NaOH或KOH,或碱土金属氢氧化物,例如Ca(OH)2、Mg(OH)2或Ba(OH)2。
更特别地,本发明的添加剂可是微粉化粉末(mirconizedpowder)的形式,优选地具有低于50μm、优选低于25μm的体积-平均尺寸。该粒径分布可通过激光衍射直接在干粉末上测定,例如在来自Malvern的S上的激光衍射。该技术基于这样的原理:穿过激光光束的颗粒根据作为它们的尺寸的不同角度衍射光线,具有小尺寸的颗粒在大角度下衍射,而具有较大尺寸的颗粒在小角度下衍射。
本发明的所述添加剂可特别地以凝胶形式用于水中使用或作为水凝胶因子和更优选在低于5%的重量含量下且还更优选不超过1重量%的含量下使用,该百分比是相对于水+添加剂的重量定义。
本发明的第二主题是根据本发明的水凝胶因子添加剂的制备方法,该方法包括脂肪酸R1CO2H和己内酰胺之间加成反应的阶段,其中所述己内酰胺相对于所述脂肪酸的摩尔比为0.8-3、优选0.9-2.75且更优选0.9-2.5,所述方法不含任何分离或纯化阶段。
该反应是在熔融状态下的批量本体加成(bulkaddition)反应,其可在200℃-300℃的温度下和在惰性气氛下或在几巴至低于30巴的压力下发生。可将催化剂用于该反应,例如,路易斯酸。冷却后,得到的产品通过机械研磨或通过在低于熔点的温度下空气喷射进行微粉化。筛分使得可获得精细且受控的粒径分布,其中体积-平均尺寸低于50μm、优选低于25μm,通过激光衍射测定,例如在来自Malvern的S上通过激光衍射测定。
本发明的另一主题是含有作为水凝胶因子的至少一种如上限定的或由本发明描述的方法得到的添加剂的含水组合物。
这样的含水组合物可为具有或不具有粘结剂(binder)的含水组合物。在不具有粘结剂的情况下,其可对应于所述添加剂在水中的简单分散体,其作为水凝胶因子起作用。水凝胶因子的效果通过随着凝胶的实现而提高的粘度来体现,通过如下事实:形成的纤维体系中分子的组合,其中水凝胶化一方面为添加剂的分子憎水性/亲水性之间的折衷,和另一方面为溶解的水平(有限但足够的)和朝向待避免的沉淀的趋势之间的折衷。这还可对应于适于去垢需求或油性产物(植物或矿物或烃来源的油)或精细分开地固体产物(颗粒形式的树脂分散体)的分散需求的含水分散剂或表面活性剂的溶液或分散体。
所述含水组合物可是有机粘结剂组合物,其可是反应性或非反应性的、单组份或二组份的、单体或低聚物或树脂或聚合物,或单体和低聚物或树脂或聚合物的混合物。因为其涉及含水介质,所述粘结剂可是水溶性的、经由其自身结构是水分散性的或使用针对含水介质的表面活性剂或分散剂在水中是可分散的。
特别的,含水组合物的pH是碱性的,优选为至少9,更优选为至少10。该pH通过过量加入的碱调节,也就是说超过所述添加剂的所述末端羧酸官能团的简单中和的添加,并且这对于水中凝胶形式的添加剂也保持同等有效。
根据第一个优选选择,所述组合物是含水粘结剂组合物且优选是含水涂料组合物,特别是含水清漆、油漆(paint)或油墨组合物,或粘合剂组合物或化妆品组合物或用于纤维或纺织品处理的组合物,其中所述水凝胶因子添加剂用作流变添加剂。
根据另一选择,所述含水组合物是表面活性剂组合物,特别是清洁剂或剥离剂或去污染剂或絮凝剂组合物。在含水粘结剂组合物中,所述酰胺添加剂作为水性凝胶因子存在以使可应用的组合物由于仅限于为所述可应用的组合物而计划的最终用途的原因而胶凝。
本发明的另一主题是根据本发明的如上限定的添加剂作为含水组合物中的水凝胶因子添加剂的用途。这样的用途已经在上文进行了描述,特别是在含水粘结剂组合物中,更特别是在含水涂料或粘合剂或化妆品组合物或用于处理纤维或纺织品的组合物中,特别是作为流变添加剂。在含水组合物中的另一用途涉及表面活性剂组合物以及特别是清洁剂、剥离剂、去污染剂或絮凝剂组合物。最终,得自本发明所述添加剂作为水性凝胶因子的用途的终产物也涵盖在本发明中,特别选自:涂料或粘合剂或化妆品或经处理的纤维或经处理的纺织品或清洁剂或剥离剂或去污染剂或絮凝剂。作为得自这些用途的产物的水凝胶也涵盖在本发明中。
以下的实施例通过说明本发明及其性能的方式呈现,且不以任何方式限制本发明的范围。
实验部分
I-所用起始材料
表1:所用起始材料
II-制备基于己内酰胺的水凝胶因子的实施例
实施例1:通过使1mol硬脂酸与1mol己内酰胺反应制备酰胺A1:
在氮气物流下,向配有温度计、冷凝器和搅拌器的1升反应器中引入113.16g己内酰胺(1mol)和284.48g硬脂酸(1mol)。然后仍在氮气物流下将混合物加热至250℃。通过粘度监测反应。15小时后,粘度值变为恒定(>0.32泊或>32mPa.s,在120℃在CAP1000上测量)和将反应混合物冷却至150℃,然后排到有机硅胶模具中。一旦冷却至环境温度,通过研磨将产物机械微粉化。实施筛分以获得精细的且受控的粒径分布,其中获得的平均尺寸为7μm。
实施例2:通过1mol硬脂酸与2mol己内酰胺反应制备酰胺A2:
在氮气气流下,向配有温度计、冷凝器和搅拌器的1升反应器中引入226.32克己内酰胺(即2mol)和284.48克硬脂酸。
其余步骤与上文实施例1中描述的相同。
III-水凝胶因子性能评价
1.用于水凝胶因子评价的配制物
将99克软化水、1克根据实施例1和2制备的磨碎的或微粉化的待测添加剂(水凝胶因子),和随后几滴高于待测水凝胶因子的羧酸当量4倍的浓氢氧化钠溶液引入到装有磁棒的Erlenmeyer烧瓶中。然后封闭Erlenmeyer烧瓶。将混合物在85℃下搅拌超过5小时以具有完全溶解的水凝胶因子添加剂,和乳状的但无沉淀物的混合物。最终将混合物引入测试管中,并在25℃下静置24小时。
在这些制备条件下,用实施例1的酰胺A1、实施例2的酰胺A2以及作为对比参照的硬脂酸生产了3个配制物。在下表2中总结了这3个测试。
表2:配制物
2.凝胶的评估
3个配制物测试以两种方式评价:首先根据24小时后测试管中制备的配制物外观(见表3)和然后且特别根据它们在不同剪切速率下在粘度计上的粘度(见表4)。
表3:外观
测试标号 | 外观 |
1 | 悬浮液 |
2 | 凝胶 |
3 | 凝胶 |
表4:不同速率下的粘度
*通过指示的方式,应当注意对比测试1的结果重复性不好,因为该配制物不是均质的。
与硬脂酸相比,由1%酰胺A1或A2获得的配制物以水凝胶因子的凝胶形式特征存在。
对于粘度结果,它们清楚地表现出含酰胺A1的配制物(测试2)不但是触变的,而且还比水或含硬脂酸的配制物更粘。
Claims (16)
1.基于脂肪酰胺的水凝胶因子添加剂,特征在于,其是脂肪酸R1CO2H与己内酰胺加成反应的产物,并且携带酸形式或通过中和剂成盐形式的末端羧基官能团,并且特征在于所述添加剂由以下物质组成或含有以下物质:3种不同酰胺化合物的混合物,所述3种不同酰胺化合物得自所述反应且特征在于引入的己内酰胺单元的数量n,该数量分别为1、2和3,其中单元的平均数量n(每分子平均)为0.8-3、优选0.9-2.75和更优选0.9-2.5。
2.根据权利要求1的添加剂,特征在于,所述3种化合物根据以下化学式(I)定义且分别对应于n=1、n=2和n=3:
R1-C(=O)-[NH(CH2)5C(=O)-]n-1-NH(CH2)5-CO2M(I)
其中M为-H或在所述成盐形式的情况下为阳离子,所述阳离子与所述中和剂相关。
3.根据权利要求1或2的添加剂,特征在于,所述脂肪酸包括10-24的碳原子数。
4.根据权利要求1-3中一项的添加剂,特征在于,所述添加剂是微粉化粉末的形式,优选地具有低于50μm、优选低于25μm的体积-平均尺寸。
5.根据权利要求1-4中一项的添加剂,特征在于其是成盐的形式且特征在于所述中和剂选自有机或无机碱。
6.根据权利要求1-5中一项的添加剂,特征在于,其是在水中的凝胶形式或作为水凝胶因子且更优选在低于5%的重量含量下且还更优选在不超过1重量%的含量下。
7.根据权利要求1-6中一项的添加剂的制备方法,特征在于,其包括脂肪酸R1CO2H和己内酰胺之间加成反应的阶段,其中所述己内酰胺相对于所述脂肪酸的摩尔比为0.8-3、优选0.9-2.75且更优选0.9-2.5,所述方法不含任何分离或纯化阶段。
8.含水组合物,特别是含水粘结剂组合物,特征在于,其含有作为水凝胶因子的至少一种根据权利要求1-6中任一项定义的添加剂或根据权利要求7定义的方法得到的添加剂。
9.根据权利要求8的组合物,特征在于,其具有碱性pH,优选至少9、更优选至少10的pH。
10.根据权利要求8或9的组合物,特征在于,其为含水粘结剂组合物,优选含水涂料组合物,特别是含水清漆、油漆或油墨组合物,或粘合剂组合物或化妆品组合物或用于处理纤维或纺织品的组合物,其中所述水凝胶因子添加剂用作流变添加剂。
11.根据权利要求8或9的组合物,特征在于,其为表面活性剂组合物,特别是清洁剂或剥离剂或去污染剂或絮凝剂组合物。
12.根据权利要求1-6中的一项定义的添加剂作为含水组合物中的水凝胶因子添加剂的用途。
13.根据权利要求12的用途,特征在于,所述添加剂用于含水粘结剂组合物中,更特别地,用在含水涂料或粘合剂或化妆品组合物中,用于处理纤维或用于处理纺织品,特别是作为流变添加剂。
14.根据权利要求12的用途,特征在于,所述添加剂用于表面活性剂组合物中,特别是清洁剂或剥离剂或去污染剂或絮凝剂组合物。
15.水凝胶,特征在于,其为由根据权利要求1-6中的一项定义的或根据权利要求7定义的方法得到的添加剂的根据权利要求12-14中的一项定义的用途获得的产物。
16.由根据权利要求1-6中的一项定义的或根据权利要求7定义的方法得到的至少一种添加剂作为水凝胶因子的用途得到的终产品,特别选自:涂料或粘合剂或化妆品或经处理的纤维或经处理的纺织品或清洁剂或剥离剂或去污染剂或絮凝剂。
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US4022606A (en) * | 1973-11-03 | 1977-05-10 | Henkel & Cie G.M.B.H. | Antimicrobial use of ω-aminocarboxylic acid amides |
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US6391844B1 (en) * | 1996-10-04 | 2002-05-21 | The Procter & Gamble Company | Process for making a detergent composition by non-tower process |
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US2956068A (en) * | 1956-08-28 | 1960-10-11 | Henkel & Compagnie G M B H | Preparation of acylamino carboxylic acids |
US4022606A (en) * | 1973-11-03 | 1977-05-10 | Henkel & Cie G.M.B.H. | Antimicrobial use of ω-aminocarboxylic acid amides |
WO1995007883A1 (en) * | 1993-09-14 | 1995-03-23 | The Procter & Gamble Company | Synthesis of amido acids from carboxylic acids and lactams |
Non-Patent Citations (4)
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A. I. RAKHIMOV ET AL.: "Importance of Acyl Rearrangement in the Acid-Catalyzed Reaction of ɛ-Caprolactam with Carboxylic Acids", 《RUSSIAN JOURNAL OF ORGANIC CHEMISTRY》 * |
Importance of Acyl Rearrangement in the Acid-Catalyzed Reaction of ɛ-Caprolactam with Carboxylic Acids;A. I. Rakhimov et al.;《Russian Journal of Organic Chemistry》;20061231;第42卷(第8期);第1252-1253页 * |
L-Lysine-based low-molecular-weight gelators;Masahiro Suzuki et al.;《Chemical Society Reviews》;20090209;第38卷;第967-975页 * |
MASAHIRO SUZUKI ET AL.: "L-Lysine-based low-molecular-weight gelators", 《CHEMICAL SOCIETY REVIEWS》 * |
Also Published As
Publication number | Publication date |
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KR20160027098A (ko) | 2016-03-09 |
EP3013791A1 (fr) | 2016-05-04 |
BR112015030478A2 (pt) | 2017-07-25 |
US20160144327A1 (en) | 2016-05-26 |
FR3007759B1 (fr) | 2015-07-24 |
JP6190054B2 (ja) | 2017-08-30 |
TWI523832B (zh) | 2016-03-01 |
TW201502113A (zh) | 2015-01-16 |
CN105339345B (zh) | 2018-01-05 |
FR3007759A1 (fr) | 2015-01-02 |
JP2016529343A (ja) | 2016-09-23 |
WO2014207343A1 (fr) | 2014-12-31 |
EP3013791B1 (fr) | 2018-01-17 |
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