CN101309899A - 氟化双子表面活性剂 - Google Patents
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Classifications
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- 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
- C11D1/004—Surface-active compounds containing F
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- Oil, Petroleum & Natural Gas (AREA)
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
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Abstract
本发明公开了一种双子表面活性剂，其由以下化学式表示：其中：每Rf独立地代表全氟丁基或全氟丙基；每个R1独立地代表具有1至6个碳原子的烷基；L1和L2代表具有2至18个碳原子的亚烷基；每个R代表具有1至6个碳原子的烷基；Z代表有机二价连接基团；并且代表具有电荷m的阴离子，其中m和n独立地为1或2，并且其中n和m的乘积为2。本发明还公开了包含所述双子表面活性剂的含水组合物。
Description
背景技术
双子表面活性剂(有时称为二聚表面活性剂)在分子中具有两个亲水性基团和两个疏水性基团，与在分子中通常具有单个亲水性基团和单个疏水性基团的传统表面活性剂形成对比。双子表面活性剂的表面活性比在分子中具有类似但仅有单个亲水性基团和疏水性基团的传统表面活性剂大十至一千倍。
发明内容
在一个方面，本发明提供了一种由以下化学式表示的双子表面活性剂：
其中
每个Rf独立地代表全氟丁基或全氟丙基；
每个R1独立地代表具有1至6个碳原子的烷基；
L1和L2代表具有2至18个碳原子的亚烷基；
每个R代表具有1至6个碳原子的烷基；
Z代表有机二价连接基团；以及
nXm-代表具有电荷m的阴离子，其中m和n独立地为1或2，并且其中n和m的乘积为2。
根据本发明，双子表面活性剂可用于例如降低含水组合物的表面张力。在一些实施例中，根据本发明的双子表面活性剂可用于增强具有分散聚合物颗粒的经涂层且干燥的含水组合物光泽。
如本文所用：
“烷基”是指衍生自烷烃的通过去除一个氢原子而得的一价基团；
“亚烷基”是指衍生自烷烃的通过去除两个氢原子而得的二价基团；
“含水的”是指包含至少25重量％的水；
“烃基”是指衍生自烃的通过去除一个氢原子而得的一价基团；
“亚烃基”是指衍生自烃的通过去除两个氢原子而得的二价基团；以及
“全氟烷基”是指所有烷基氢原子均被氟原子取代的烷基。
具体实施方式
根据本发明的双子表面活性剂由以下化学式表示：
每个Rf独立地代表全氟丁基(例如-CF2CF2CF2CF3或-CF2CF(CF3)2)或全氟丙基(例如-CF2CF2CF3或-CF(CF3)2)。
每个R1独立地代表具有1至6个碳原子的烷基(例如甲基、乙基、丙基、己基)。
L1和L2代表具有2至4、2至12、或2至18个碳原子的亚烷基。实例包括亚乙基、亚丙基、亚丁基、亚己基、1，12-亚十二烷基和1，18-亚十八烷基。L可以是直链或支链的，并且可以包含一个或多个环。
每个R代表具有1至6个碳原子的烷基(例如甲基、乙基、丙基、己基)。
Z代表有机二价连接基团。在一些实施例中，Z具有2至10、2至20、或2至30个碳原子。适宜有机二价连接基团的实例包括亚烃基，例如具有2至10、20或30个碳原子的二价无环脂族基团(例如亚乙基、1，3-亚丙基、1，2-亚丙基、1，10-亚癸基、1，30-亚十三烷基)；具有3至10、20或30个碳原子的二价脂环烃基(例如，1，2-亚环丙基、1，4-亚环己基、或二(1-环己基-4-基)丙烷)；具有7至15、20或30个碳原子的混合的二价脂肪族芳族基团(例如
在一些实施例中，Z选自由下列物质组成的组：具有2至30个碳原子的二价亚烃基，一个或多个具有2至30个碳原子的亚烃基与至少一个-O-(例如-CH2CH2O-或-(CH(CH3)CH2)O)10-)、-S-、或-NR2-的组合，其中R2代表H或具有1至12个碳原子的烃基(例如，Z可以是-CH2CH2N(CH3)CH2CH2-)。
nXm-代表具有电荷m的阴离子(例如，如果n＝2)，其中m和n独立地为1或2，并且其中n和m的乘积为2。适宜阴离子的实例包括卤素离子(例如氯离子、溴离子或碘离子)、烷基磺酸根(例如甲磺酸根、三氟甲磺酸根)；芳基磺酸根(例如对甲苯磺酸根)；氢氧根、链烷羧酸根(例如乙酸根、延胡索酸根或酒石酸根)和复合的金属卤素离子(例如BF4 -、SbF6 -或PF6 -)。
通常，为有利于合成，两个Rf基团可相同，两个L基团可相同，并且所有的R基团可相同，但是这不是必须的。
根据本发明，双子表面活性剂的便捷合成路线包括，通过例如使由化学式RfSO2NR1-L-NR2表示的物质与二烷基化剂X-Z-X(例如，其中X为单价)反应生成季铵盐，其中Rf、R1、L和R如上定义。适宜二烷基化剂的实例包括1，4-二(氯甲基)苯；1，6-二溴己烷；或1，11-二氯-3，6，9-三氧杂十一碳烷。
由化学式RfSO2NR1-L-NR2表示的物质的可用合成路线包括，例如，使由化学式RfSO2NR1-L-X表示的物质与二烷基胺R2NH反应。通过使RfSO2NHR1与氨基烷基化剂例如ClC2H4N(CH3)2或类似物反应，可制得RfSO2NR1-L-NR2。通过在吡啶中，用亚硫酰氯(即SOCl2)或甲磺酰氯(即CH3SO2Cl)处理相应的醇RfSO2NR1-L-OH如C4F9SO2N(CH3)CnH2nOH，其中n为2或4，可制得RfSO2NR1-L-X(例如，其中X为Cl或OSO2CH3)。
本发明的表面活性剂基本上不含(也就是说，小于1重量％)从活体中排去缓慢的含氟化合物，因此与其它大多数已知可商购获得的基于含较长全氟化链段或端基表面活性剂的含氟化合物相比，其被认为是环境可持续发展的。
许多先前已知的含氟化合物包含全氟辛基部分。这些表面活性剂最终降解成包含全氟辛基的化合物。已报导，某些包含全氟辛基的化合物趋于在活体中生物体内积累。这种趋向已作为涉及一些含氟化合物潜在问题而被提出。例如，参见美国专利No.5,688,884(Baker等人)。因此，需要包含氟化表面活性剂的组合物，所述组合物可有效提供所期望的表面活性剂特性，并且可控更有效地从体内排去(包括所述组合物和其降解产物)。
预计包含全氟丁基或全氟丙基的本发明氟化双子表面活性剂在存在于环境中的生物、热、氧化、水解和光解条件作用下，分解成多种降解产物。例如，预计包含全氟丁磺酰胺基团的组合物在至少一定程度上最终降解成全氟丁磺酸盐。已令人惊奇地发现，以其钾盐形式测试的全氟丁磺酸盐可比全氟己磺酸盐更有效地从体内排去，并且比全氟辛磺酸盐更加有效。
根据本发明，氟化双子表面活性剂可用于含水的或非水的组合物中，并且通常可有效降低包含有机溶剂和/或水的制剂的表面张力。根据本发明，氟化双子表面活性剂的用途包括例如消泡乳化剂、分散剂、润湿助剂或均质助剂。在一些实施例中，根据本发明，氟化双子表面活性剂可包含于含水组合物中，包括其中具有分散聚合物乳胶颗粒(例如丙烯酸乳胶颗粒)的那些。
本发明的主题和优点可进一步由以下非限制性实例来说明，但是这些实例中所叙述的具体物质及其用量以及其它条件和细节不应被不当地解释为是对本发明的限制。
实例
除非另外指明，实例和说明书其它部分中的所有份数、百分比、比率等均按重量计，并且实例中所用的所有试剂均获自或可得自一般的化学品供应商，例如Sigma-Aldrich Company、Saint Louis、Missouri，或可通过传统方法合成。
表面张力
使用去离子水，将所有产品稀释至指定的浓度。使用Kruss K-12张力计和Du Nouy环方法，在20℃下测定静态表面张力。在相同条件下，使用Sensadyne 5000最大气泡压张力计(可得自Data PhysicsInstruments，Germany)，以4个气泡/秒的气泡速率，在20℃下测定动态表面张力。
制备C
4
F
9
SO
2
N(CH
3
)CH
2
CH
2
N
+
(CH
3
)
2
CH
2
C
6
H
4
CH
2
N
+
(CH
3
)
2
-
CH
2
CH
2
N(CH
3
)SO
2
C
4
F
9
(Cl
-
)
2
(GS1)
将28.8克(g)二甲基氨乙基氯盐酸盐、62.6g C4F9SO2NHCH3(如美国专利No.6,664,354(Savu等人)实例1部分A中所述制备)、40g 50％重量NaOH水溶液和100mL四氢呋喃的溶液回流搅拌2.5小时(hr)。气-液色谱显示转化完全。用水洗涤混合物，用二氯甲烷萃取，并且去除溶剂获得49.3g物质。在120℃/0.2mmHg(30Pa)下将所述物质蒸馏，获得C4F9SO2N(CH3)CH2CH2N(CH3)2，得到45.0g静置固化的棕褐色液体。当7.7g的将固化棕褐色液体与1.75g 1，4-二(氯甲基)苯的10mL乙腈溶液在蒸汽浴上加热时，立即获得沉淀。加入更多的乙腈(15mL)，并且将所述混合物在50至60℃下加热8hr，然后用75mL二乙基醚稀释，并且过滤和干燥，获得7.4g GS1，为白色的盐。去离子水中的静态表面张力：在按重量计25.3份每一百万份(ppm)的浓度下，为31.5达因/厘米(0.315毫牛顿/厘米)；在65.1ppm的浓度下，为21.0达因/厘米(0.210毫牛顿/厘米)；在127.6ppm的浓度下，为19.5达因/厘米(0.195毫牛顿/厘米)。在按重量计浓度为0.5％的水中，GS1的动态表面张力为20.5达因/厘米。
在地板漆中GS1的评价
含水苯乙烯-丙烯酸乳状液地板漆得自Cook Composites andPolymers(Kansas City，Missouri)，其与以商品名“SHIELD-8”由CookComposites and Polymers销售的那个相同；不同的是没有氟化表面活性剂(以商品名“ZONYL FSN”得自E.I.du Pont de Nemours & Co.，Wilmington，Delaware)和水溶胶乳状液均质剂(以商品名“ESI-CRYL842”得自Cook Composites and Polymers)。通过加入100ppm或200ppm含量的GS1，或用于商业地板漆中的对比性氟化表面活性剂(即得自3M Company的“FLUORAD FC-129”)，来制备用于测试的这种地板漆(即FF1)的样本。
将5mL包含100或200ppm含氟化合物表面活性剂的液体地板漆施用到12″x12″预清洁的黑色乙烯基复合地面砖中央，然后使用一块覆盖地面砖整个表面积的薄纱或粗棉布将其铺展，直至获得均匀的涂层。使用覆盖地面砖整个表面积的8字形反复运动施用涂层，直至获得均匀的涂层。然后通过在地面砖对角之间涂布地板漆，来获得“X”。重复所述过程，直至施用共计五层涂层，在再次施用之前，使每一个涂层干燥至少25至30分钟。
所述地面砖涂布有五道地板漆，并且使经涂布的地面砖风干至少7天，然后使用以商品名“MICRO-TRI-GLOSS METER”得自Paul N.Gardner Co.，Inc.(Pompano Beach，Florida)的BYK-Gardner光泽计，测定60°光泽度，取在地面砖涂布表面上六次不同测定的平均值。光泽度量度记录于表1(下文)，并且其中“FS1”是指以商品名“FLUORAD FC-129”得自3M Company的氟化表面活性剂。
表1
| 实例 | 表面活性剂 | 表面活性剂的浓度 | 60°光泽度 |
| FF1 | GS1 | 100ppm | 79 |
| FF2 | GS1 | 200ppm | 89 |
| 对比物1 | FS1 | 100ppm | 62 |
| 对比物2 | FS1 | 200ppm | 62 |
在不脱离本发明的范围和精神的前提下，本领域的技术人员可对本发明进行多种修改和更改，而且应该理解，本发明不受本文中所述示例性实施例的不当限制。
Claims (15)
1.一种双子表面活性剂，由以下化学式表示：
其中
每个Rf独立地代表全氟丁基或全氟丙基；
每个R1独立地代表具有1至6个碳原子的烷基；
L1和L2代表具有2至18个碳原子的亚烷基；
每个R代表具有1至6个碳原子的烷基；
Z代表有机二价连接基团；以及
nXm-代表具有电荷m的阴离子，其中m和n独立地为1或2，并且其中n和m的乘积为2。
2.根据权利要求1所述的双子表面活性剂，其中至少一个Rf为全氟丁基。
3.根据权利要求1所述的双子表面活性剂，其中至少一个R或R1为甲基。
4.根据权利要求1所述的双子表面活性剂，其中至少一个L代表具有2至4个碳原子的亚烷基。
5.根据权利要求1所述的双子表面活性剂，其中至少一个R代表甲基。
6.根据权利要求1所述的双子表面活性剂，其中Z选自由下列物质组成的组：具有2至30个碳原子的二价亚烃基，一个或多个具有2至30个碳原子的亚烃基与至少一个羰基、-O-、-S-或-NR2-的组合，其中R2代表H或具有1至12个碳原子的烃基。
7.根据权利要求1所述的双子表面活性剂，其中Z代表亚烃基。
8.根据权利要求1所述的双子表面活性剂，其中Z代表
9.根据权利要求1所述的双子表面活性剂，其中X选自由下列物质组成的组：卤素离子、烷基磺酸根、芳基磺酸根、氢氧根、链烷羧酸根和复合的金属卤化物离子。
10.一种含水组合物，包含水和根据权利要求1所述的双子表面活性剂。
11.根据权利要求10所述的含水组合物，还包含分散的聚合物乳胶。
12.根据权利要求1所述的双子表面活性剂，其中所述表面活性剂包含至少一种具有以下化学式的物质
13.一种含水组合物，包含水和至少一种根据权利要求1所述的双子表面活性剂。
14.根据权利要求13所述的含水组合物，还包含分散的聚合物颗粒。
15.根据权利要求14所述的含水组合物，其中X选自由下列物质组成的组：卤素离子、烷基磺酸根、芳基磺酸根、氢氧根、链烷羧酸根和复合的金属卤化物离子。
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| PCT/US2006/043591 WO2007061637A2 (en) | 2005-11-17 | 2006-11-09 | Fluorinated gemini surfactants |
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| CN102489216A (zh) * | 2011-12-06 | 2012-06-13 | 华中师范大学 | 两性含氟离子型表面活性剂的制备方法与应用 |
| CN103950311A (zh) * | 2014-04-29 | 2014-07-30 | 江门市蓬江区荷塘镇诚信精细化工厂 | 一种免酒精润版液中的醇替代物及其制备方法 |
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| KR20060113907A (ko) | 2003-09-29 | 2006-11-03 | 에테나 헬스케어 인코포레이티드 | 높은 알코올 함량의 겔-유사 및 포옴 조성물 |
| DE102004062775A1 (de) | 2004-12-21 | 2006-06-29 | Stockhausen Gmbh | Alkoholischer Pumpschaum |
| US8263098B2 (en) | 2005-03-07 | 2012-09-11 | Deb Worldwide Healthcare Inc. | High alcohol content foaming compositions with silicone-based surfactants |
| US20070148101A1 (en) * | 2005-12-28 | 2007-06-28 | Marcia Snyder | Foamable alcoholic composition |
| US7684332B2 (en) * | 2006-08-22 | 2010-03-23 | Embarq Holdings Company, Llc | System and method for adjusting the window size of a TCP packet through network elements |
| US8580860B2 (en) * | 2007-02-23 | 2013-11-12 | Gojo Industries, Inc. | Foamable alcoholic composition |
| US7385077B1 (en) | 2007-03-27 | 2008-06-10 | E. I. Du Pont De Nemours And Company | Fluoroalkyl surfactants |
| CN101314692A (zh) * | 2007-05-30 | 2008-12-03 | 3M创新有限公司 | 水性涂料组合物 |
| US7638650B2 (en) * | 2007-08-06 | 2009-12-29 | E.I. Du Pont De Nemours And Company | Fluoroalkyl surfactants |
| US7399887B1 (en) | 2007-08-06 | 2008-07-15 | E. I. Du Pont De Nemours And Company | Fluorinated sulfonate surfactants |
| US7728163B2 (en) * | 2007-08-06 | 2010-06-01 | E.I. Du Pont De Nemours And Company | Mixed fluoroalkyl-alkyl surfactants |
| US8242309B2 (en) | 2009-09-16 | 2012-08-14 | Living Proof, Inc. | Cationic alcohols and uses thereof |
| WO2012088216A2 (en) | 2010-12-21 | 2012-06-28 | 3M Innovative Properties Company | Method for treating hydrocarbon-bearing formations with fluorinated amine |
| DE102012022441A1 (de) | 2012-11-15 | 2014-05-28 | Merck Patent Gmbh | Neue Phosphinsäureamide, deren Herstellung und Verwendung |
| CN106634894B (zh) * | 2017-01-18 | 2018-02-06 | 中国石油大学(北京) | 双阳离子氟碳表面活性剂及其制备方法和作为双疏型润湿反转剂的应用和钻井液及其应用 |
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| US4167639A (en) | 1973-06-09 | 1979-09-11 | Hoechst Aktiengesellschaft | Fluorinated sulfosuccinates |
| US4841090A (en) | 1982-06-11 | 1989-06-20 | Minnesota Mining And Manufacturing Company | Treatment of fibrous substrates, such as carpet, with fluorochemical |
| US4823873A (en) | 1987-12-07 | 1989-04-25 | Ciba-Geigy Corporation | Steam mediated fluorochemically enhanced oil recovery |
| FR2641781B1 (fr) * | 1988-12-27 | 1991-04-19 | Atochem | Acetates, thioacetates et acetamides de polyfluoroalkyle substitues, leurs procedes de preparation et leur application |
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| US5688884A (en) | 1995-08-31 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
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| DE19608117A1 (de) * | 1996-03-02 | 1997-09-04 | Huels Chemische Werke Ag | Betain-Geminitenside auf der Basis von Aminen |
| US6200369B1 (en) | 1999-04-28 | 2001-03-13 | Xerox Corporation | Ink compositions |
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2005
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102489216A (zh) * | 2011-12-06 | 2012-06-13 | 华中师范大学 | 两性含氟离子型表面活性剂的制备方法与应用 |
| CN102489216B (zh) * | 2011-12-06 | 2014-01-22 | 华中师范大学 | 两性含氟离子型表面活性剂的制备方法与应用 |
| CN103950311A (zh) * | 2014-04-29 | 2014-07-30 | 江门市蓬江区荷塘镇诚信精细化工厂 | 一种免酒精润版液中的醇替代物及其制备方法 |
| CN103950311B (zh) * | 2014-04-29 | 2016-04-06 | 江门市蓬江区荷塘镇诚信精细化工厂 | 一种免酒精润版液中的醇替代物及其制备方法 |
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| CN101309899B (zh) | 2012-07-18 |
| US7164041B1 (en) | 2007-01-16 |
| JP5032492B2 (ja) | 2012-09-26 |
| EP1957445A2 (en) | 2008-08-20 |
| KR20080067347A (ko) | 2008-07-18 |
| EP1957445B1 (en) | 2012-08-01 |
| JP2009515965A (ja) | 2009-04-16 |
| WO2007061637A2 (en) | 2007-05-31 |
| EP1957445A4 (en) | 2011-04-20 |
| BRPI0618616A2 (pt) | 2011-10-18 |
| WO2007061637A3 (en) | 2007-07-12 |
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