CN108203484B - 用精氨酸官能化单体结构单元官能化的乳胶 - Google Patents

用精氨酸官能化单体结构单元官能化的乳胶 Download PDF

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CN108203484B
CN108203484B CN201711187298.1A CN201711187298A CN108203484B CN 108203484 B CN108203484 B CN 108203484B CN 201711187298 A CN201711187298 A CN 201711187298A CN 108203484 B CN108203484 B CN 108203484B
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polymer particles
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methacrylate
arginine
structural units
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CN108203484A (zh
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J·C·勃林
A·S·布朗奈尔
M·塞西欧萨姆
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Rohm and Haas Co
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Abstract

本发明涉及一种包含聚合物颗粒的稳定水性分散液的组合物，所述聚合物颗粒包含可聚合氨基酸的结构单元和酸单体或其盐的结构单元。本发明的组合物可用于改善涂料组合物对唇膏污渍的抗性。

Description

用精氨酸官能化单体结构单元官能化的乳胶
背景技术
本发明涉及一种组合物，所述组合物包含用精氨酸官能化单体结构单元官能化的聚合物颗粒的稳定水性分散液(即，乳胶)。本发明的组合物可用于涂料配制物中。
使涂料级乳液聚合物配制的涂料具有卓越的抗污性和/或污渍阻隔性对于配制者来说一直是一种挑战，这部分是因为通常很难在改善抗污性与同时造成的对其它油漆性能特性的不利影响之间达成平衡。疏水性污渍抗性的改善通常与对亲水性污渍抗性的损害相关，又增加了问题的复杂性。
举例来说，已知使用浓度超过2重量％的月桂基硫酸钠表面活性剂可以对许多疏水性污渍产生正面影响，但同时会损害抗水性和亲水性污渍抗性，而且还会加剧表面活性剂沥出和水渍。
将甲基丙烯酸磷酸乙酯(PEM)并入涂料配制物的粘合剂中可以大大提高针对亲水性污渍(具体地说，咖啡)的抗性；然而，已知PEM在造漆工艺期间会加剧粗粒形成。另外，在某些配方原材料(如某些类型的绿坡缕石或膨润土)存在下，含有PEM的聚合物通常展现有限的相容性。
丙烯酸乙酯(EA)官能化的聚合物颗粒对唇膏污渍特别具有抗性，但为了看到这种作用，通常需要EA的浓度超过总乳胶颗粒组合物的20％，由此限制了其它单体的选择。此外，EA具有非常低的气味阈值，因此需要彻底地消除残余单体且有时成本高昂。
另外，用于实现胶体稳定性的多种酸单体或佐剂，如表面活性剂和过硫酸盐，会对抗污性产生负面影响。因此，找到一种在抗污性与其它性能特性之间达成良好平衡的方式在抗污技术中将是一个进步。
发明内容
本发明通过提供一种包含聚合物颗粒的水性分散液的组合物解决了本领域中的需求，所述聚合物颗粒包含0.02到4重量％的酸单体或其盐的结构单元；以及0.05到3重量％的精氨酸官能化单体的结构单元，所述精氨酸官能化单体由以下结构表征：
Figure BDA0001479485030000021
其中X是NH、NHCH2CH2O、NHCH2CH2NR或NHCH2CH(OH)CH2O；并且R各自独立地是H或CH3。
本发明的组合物特别有效地改善油漆对唇膏污渍的抗性。
具体实施方式
本发明是一种包含聚合物颗粒的水性分散液的组合物，所述聚合物颗粒包含0.02到4重量％的酸单体或其盐的结构单元；以及0.05到3重量％的精氨酸官能化单体的结构单元，所述精氨酸官能化单体由以下结构表征：
Figure BDA0001479485030000022
其中X是NH、NHCH2CH2O、NHCH2CH2NR或NHCH2CH(OH)CH2O；并且R各自独立地是H或CH3。
优选的是，X是NH且R是CH3。
如本文所用，术语“聚合物颗粒的水性分散液”与“乳胶”一词同义。
如本文所用，术语“结构单元”是指单体在聚合之后的残余物。举例来说，N2-精氨酸甲基丙烯酸酯的结构单元如下所示：
Figure BDA0001479485030000023
N2-精氨酸甲基丙烯酸酯的结构单元
其中虚线表示与聚合物主链的连接点。优选的是，聚合物颗粒中的精氨酸官能化甲基丙烯酸酯，优选聚合物颗粒中的N2-精氨酸甲基丙烯酸酯的结构单元的浓度以聚合物颗粒的重量计是从0.1重量％，更优选从0.2重量％并且最优选从0.25重量％到2重量％，更优选到1重量％并且最优选到0.75重量％。应了解，精氨酸官能化单体的结构单元包括盐及其两性离子。
N2-精氨酸甲基丙烯酸酯宜通过使精氨酸与甲基丙烯酸酐在室温下接触来制备。
精氨酸官能化甲基丙烯酸酯的其它实例包括N2-(2-羟基-3-(甲基丙烯酰氧基)丙基-精氨酸，它可以通过N2-精氨酸与甲基丙烯酸缩水甘油酯反应来制备：
Figure BDA0001479485030000031
N2-(2-羟基-3-(甲基丙烯酰氧基)丙基-精氨酸；
以及N2-(2-(甲基丙烯酰氧基)乙基)-精氨酸，宜通过精氨酸与甲基丙烯酸2-羟基乙酯的缩合反应制备。
Figure BDA0001479485030000032
N2-(2-(甲基丙烯酰氧基)乙基)-精氨酸
如本文所用，术语“酸单体”是含有可电离质子的烯系不饱和单体。适合的酸单体种类包括羧酸、硫酸、磷酸单体。羧酸单体和其盐的实例包括丙烯酸、甲基丙烯酸和衣康酸(itaconic acid)及其盐；适合的硫酸单体的实例包括甲基丙烯酸磺乙酯、甲基丙烯酸磺丙酯、苯乙烯磺酸、乙烯基磺酸和2-丙烯酰胺基-2-甲基丙磺酸，以及其盐。
适合的磷酸单体的实例包括醇的膦酸酯和磷酸二氢酯，其中所述醇含有可聚合乙烯基或烯烃基团，或被所述基团取代。优选的磷酸二氢酯是丙烯酸羟基烷酯或甲基丙烯酸羟基烷酯的磷酸酯，包括甲基丙烯酸磷酸乙酯(PEM)和甲基丙烯酸磷酸丙酯。PEM是特别优选的磷酸单体，由以下结构表示：
Figure BDA0001479485030000041
其中R是H或
Figure BDA0001479485030000042
优选的是，酸单体的结构单元的浓度以聚合物颗粒的重量计是在从0.05重量％，更优选从0.1重量％并且最优选从0.3重量％到优选6重量％，更优选到4重量％并且更优选到2重量％范围内。酸单体还可以是酸单体的组合，例如以聚合物颗粒的重量计浓度优选在从0.1重量％，更优选从0.2重量％并且最优选从0.5重量％到优选5重量％，更优选到3重量％并且最优选到2重量％范围内的磷酸单体；以及以聚合物颗粒的重量计浓度优选在从0.1重量％，更优选从0.2重量％并且最优选从0.5重量％到优选4重量％，更优选2.5重量％范围内的羧酸单体。
聚合物颗粒优选是丙烯酸类聚合物颗粒。如本文所用，术语“丙烯酸类聚合物颗粒”是指以聚合物颗粒的重量计包含至少25重量％的甲基丙烯酸酯或丙烯酸酯单体的结构单元或其组合的聚合物颗粒(包括种子聚合物颗粒)。优选的是，丙烯酸类聚合物颗粒包含从50重量％，更优选从80重量％并且最优选从90重量％到99.9重量％，更优选到98重量％并且最优选到96重量％的丙烯酸酯或甲基丙烯酸酯单体的结构单元或其组合。优选的是，聚合物颗粒包含一种或多种甲基丙烯酸酯单体，如甲基丙烯酸甲酯、甲基丙烯酸乙酯或甲基丙烯酸丁酯；以及b)一种或多种丙烯酸酯单体，如丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-丙基庚酯或丙烯酸2-乙基己酯。
丙烯酸类聚合物颗粒还可以包含0.1到0.5重量％的多烯系不饱和单体的结构单元，如二乙烯基苯或甲基丙烯酸烯丙酯，并且还可以包含其它单体的结构单元，如以聚合物颗粒的重量计在5到50重量％范围内的苯乙烯，和以聚合物颗粒的重量计在50到75重量％范围内的乙酸乙烯酯。
聚合物颗粒的形态并不重要。聚合物颗粒可以借助于单段或多段聚合反应制备；其可以具有球形形态或橡果形态，其中核部分从聚合物颗粒的壳部分凸出；并且其可以是颜料吸附(例如TiO2吸附)型聚合物颗粒，但这不是必须的。
本发明的组合物还有利地包括颜料，如TiO2，和其它添加剂，如消泡剂、表面活性剂、分散剂、流变改性剂、杀生物剂以及中和剂。已经意外地发现，由本发明组合物形成的涂料，尤其是油漆，对唇膏污渍显示出明显的抗性，而且不会对油漆的其它性能特性产生不利影响。
实例
比较实例1-未用N2-精氨酸甲基丙烯酸酯官能化的双形态吸附型乳胶的制备
A.核(预成形体)合成
通过将去离子水(200g)、Disponil FES 993表面活性剂(43g，30％活性)、丙烯酸丁酯(371.2g)、甲基丙烯酸甲酯(195.2g)、甲基丙烯酸烯丙酯(9.6g)、甲基丙烯酸磷酸乙酯(51.2g，60％活性)以及甲基丙烯酸(12.8g)混合来制备第一单体乳液(ME1)。向配备有桨式搅拌器、温度计、氮气入口以及回流冷凝器的5L四颈圆底烧瓶中添加去离子水(600g)和Disponil FES 32表面活性剂(43g，30％活性)。在N2下将烧瓶的内含物加热到85℃，并且开始搅拌。然后添加一部分ME1(70g)，随后迅速添加过硫酸钠(2.56g)溶解于去离子水(30g)中的溶液，随后添加去离子水冲洗液(5g)。搅拌10分钟之后，以线性方式经40分钟分别依序添加ME1的其余部分、冲洗液(25g)，以及过硫酸钠(0.64g)溶解于去离子水(50g)中的引发剂溶液。在ME1进料完成之后，使烧瓶的内含物在85℃下保持10分钟，之后完成共进料并且然后使烧瓶的内含物在85℃下再保持10分钟。将烧瓶的内含物冷却到室温，并且用稀氢氧化铵溶液中和到pH3。使用Brookhaven BI 90Plus颗粒分析议测量到粒度是60-75nm并且固体是40％。
B.橡果核-壳合成
使用去离子水(400g)、十二烷基苯磺酸钠(55.4g，23％活性)、Disponil FES 993表面活性剂(48.17g，30％活性)、丙烯酸丁酯(775.2g)、甲基丙烯酸甲酯(797.33g)、脲基甲基丙烯酸酯(44.2g，50％活性)、丙烯酸(10.2g)以及4-乙烯基苯磺酸钠(11.33g，90％活性)制备第二单体乳液(ME2)。
向配备有桨式搅拌器、温度计、N2入口以及回流冷凝器的5L四颈圆底烧瓶中添加去离子水(850g)和Disponil FES 993表面活性剂(5.65g，30％活性)。在N2下将烧瓶的内含物加热到84℃，并且开始搅拌。然后添加一部分ME2(75g，占总单体的3.5％)，随后迅速添加过硫酸铵(5.1g)溶解于去离子水(25g)中的水溶液，随后添加去离子水冲洗液(5g)。搅拌10分钟之后，然后添加来自步骤A的一部分预成形体(212.5g，占总单体的5.0％)，随后添加ME2的其余部分且然后添加含有溶解于去离子水(55g)中的过硫酸铵(1.7g)和氢氧化铵(5g，29％活性)的溶液，这些各自以线性方式分别添加到烧瓶中，总共历时80分钟。在添加第二单体乳液期间，使烧瓶的内含物维持在84℃的温度。当所有添加都完成时，用去离子水(25g)冲洗含有第二单体乳液的容器，然后将其添加到烧瓶中。
将烧瓶的内含物冷却到65℃，并且向烧瓶中添加催化剂/活化剂对以减少残余单体。添加TERGITOLTM 15-S-40表面活性剂(陶氏化学公司(The Dow Chemical Company)或其附属公司的商标，12.15g，70％固体)。然后用稀氢氧化铵溶液将聚合物中和到pH9。使用Brookhaven BI 90 Plus颗粒分析议测量到粒度是122nm并且固体是49.5％。
比较实例2-未用N2-精氨酸甲基丙烯酸酯官能化的2阶段球状吸附型乳胶的制备
通过将去离子水(200g)、Disponil FES 993表面活性剂(34g，30％活性)、丙烯酸丁酯(309.4g)、甲基丙烯酸甲酯(252.62g)、甲基丙烯酸磷酸乙酯(30.6g，60％活性)以及4-乙烯基苯磺酸钠(2.64g，90％活性)混合来制备ME1。
使用去离子水(300g)、Disponil FES 32表面活性剂(28.33g，30％活性)、丙烯酸丁酯(574.6g)、甲基丙烯酸甲酯(449.48g)、脲基甲基丙烯酸酯(51g，50％活性)、甲基丙烯酸乙酰乙酰氧基乙酯(53.68g，95％活性)以及4-乙烯基苯磺酸钠(4.92g，90％活性)制备ME2。
向配备有桨式搅拌器、温度计、N2入口以及回流冷凝器的5L四颈圆底烧瓶中添加去离子水(900g)和Disponil FES 32表面活性剂(5.65g，30％活性)。在N2下将烧瓶的内含物加热到85℃，并且开始搅拌。接着添加一部分ME1(105g)，随后迅速添加过硫酸铵(5.1g)溶解于去离子水(25g)中的水溶液，随后添加去离子水冲洗液(5g)。搅拌10分钟之后，以线性方式向烧瓶中分别添加ME1的其余部分和含有溶解于去离子水(30g)中的过硫酸铵(0.67g)的溶液，总共历时45分钟。在ME1添加完之后，用去离子水(25g)冲洗含有ME1的容器，然后将其添加到烧瓶中，并使烧瓶的内含物在85℃温度下维持15分钟。以线性方式将ME2和含有溶解于去离子水(50g)中的过硫酸铵(1.03g)的溶液分别添加到烧瓶中，总共历时70分钟。在ME2添加20分钟之后，在添加ME2的同时，以线性方式将含有溶解于去离子水(20g)中的氢氧化铵(10g，29％活性)的溶液单独地添加到烧瓶中。所有添加完成时，用去离子水(25g)冲洗含有ME2的容器，然后将其添加到烧瓶中。
将烧瓶的内含物冷却到70℃，并且向烧瓶中添加催化剂/活化剂对以减少残余单体。然后用稀氢氧化铵溶液将聚合物中和到pH9.3。使用Brookhaven BI 90Plus颗粒分析议测量到粒度是109nm并且固体是48.0％。
比较实例3-未用N2-精氨酸甲基丙烯酸酯官能化的球状非吸附型乳胶的制备
通过将去离子水(800g)、月桂基硫酸钠(16.59g，28％活性)、丙烯酸丁酯(957.95g)、甲基丙烯酸甲酯(977.53g)以及甲基丙烯酸(19.52g)混合来制备单体乳液。
向装备有桨式搅拌器、温度计、N2入口以及回流冷凝器的5L四颈圆底烧瓶中添加去离子水(700g)、月桂基硫酸钠(19.73g，28％活性)，以及碳酸钠(6.8g)溶解于去离子水(67g)中的溶液。在N2下将烧瓶的内含物加热到88℃，并且开始搅拌。然后添加一部分单体乳液(59g)，随后迅速添加过硫酸铵(6.8g)溶解于去离子水(25g)中的水溶液，随后添加去离子水冲洗液(5g)。搅拌10分钟之后，分别将单体乳液的其余部分以及含有溶解于去离子水(99g)中的过硫酸铵(1.04g)的溶液添加到烧瓶中，总共历时65分钟。单体乳液添加完之后，用去离子水(25g)冲洗含有单体乳液的容器，然后将其添加到烧瓶中，并且使烧瓶的内含物在88℃温度下维持5分钟。
使烧瓶的内含物冷却到75℃，并且向烧瓶中添加催化剂/活化剂对以减少残余单体。接着用稀氢氧化铵溶液将聚合物中和到pH8.5。使用Brookhaven BI 90Plus颗粒分析议测量到粒度是140nm并且固体是50.6％。
实例1-用N2-精氨酸甲基丙烯酸酯官能化的双形态吸附型乳胶的制备
基本上如比较实例1中所述制备乳胶，不过在B部分中，将甲基丙烯酸甲酯的量减少17g达到780.33g并且将N2-精氨酸甲基丙烯酸酯(42.5g，40％活性)添加到ME2混合物中。使用Brookhaven BI 90Plus颗粒分析议测量到粒度是128nm并且固体是49.2％。
实例2-用N2-精氨酸甲基丙烯酸酯官能化的2阶段球状吸附型乳胶的制备
基本上如比较实例2中所述制备乳胶，不过将ME2中甲基丙烯酸甲酯的量减少8.5g达到440.98g且将N2-精氨酸甲基丙烯酸酯(21.2g，40％活性)添加到ME2混合物中。使用Brookhaven BI 90Plus颗粒分析议测量到粒度是106nm并且固体是48.4％。
实例3-用N2-精氨酸甲基丙烯酸酯官能化的球状非吸附型乳胶的制备
基本上如比较实例3中所描述制备乳胶，不过单体混合物中甲基丙烯酸甲酯的量减少9.8g达到967.73g并且将N2精氨酸甲基丙烯酸酯(24.5g，40％活性)添加到单体乳液混合物中。使用Brookhaven BI 90Plus颗粒分析议测量到粒度是131 nm并且固体是50.6％。
表1显示了制备油漆配制物所用的材料和步骤，对所述油漆配制物进行唇膏污渍抗性测试。粘合剂是指由实例1和2以及比较实例1和2制备的乳胶。Ultra是指ROPAQUETMUltra不透明聚合物；Kronos 4311是指Kronos 4311TiO2浆料；Tamol 2011是指TAMOLTM2011分散剂；Tergitol 15-S-40是指TERGITOLTM15-S-40表面活性剂；ASP 170是指ASP170高岭粘土；Minex 10是指Minex 10霞石正长岩；Attagel 50是指Attagel 50增量剂；Optifilm 400是指Optifilm 400聚结剂。ROPAQUE、TAMOL和TERGITOL都是陶氏化学公司或其附属公司的商标。
表1-使用实例1和2以及比较实例1和2的油漆配制物
Figure BDA0001479485030000081
表3显示了制备另一油漆配制物所用的材料和步骤，对所述油漆配制物进行唇膏污渍抗性测试。粘合剂是指由实例3和比较实例3制备的乳胶。
表2-包括来自实例3和比较实例3的粘合剂的油漆配制物
Figure BDA0001479485030000091
表3比较了实例和比较性中间物实例的粒度和pH值；PS是指聚合物颗粒的平均粒度。
表3-粒度和pH值比较
实例编号 PS(nm) pH
1 128 9.3
比较实例1 122 9.0
2 106 9.3
比较实例2 109 9.4
3 131 8.5
比较实例3 140 8.5
结果表明通过将N2-精氨酸甲基丙烯酸酯官能团包括在聚合物颗粒中对胶体稳定性无明显有害影响并且不会失去粒度控制。
污渍测试程序(根据ASTM方法D4828改编)
使用7密耳(湿)陶氏施料器(Dow applicator)将测试油漆浇注于黑色乙烯卡片上，并且在测试油漆附近浇注对照油漆。在77°F(25℃)和50％相对湿度下干燥油漆七天。横过测试板对二分之一英寸截面作出标记并均匀地涂覆唇膏以填满测试区域。使污渍浸入约2小时。将3″×4″海绵浸泡于自来水中并挤压直到再没有水从海绵中滴出。然后将海绵附着到1kg带磨粒的船型器皿上并将10mL充分混合的Leneta标准化无磨粒擦洗介质(Standardized Non-Abrasive Scrub Medium)和15mL自来水施加到海绵的暴露表面上。然后使用GARDCO可洗性及磨损测试仪(型号D10WA-2151)，使用1kg船型器皿将面板擦洗100个循环。用水充分地冲洗面板并使其干燥；使用BYK Spectro-guide色差仪45/0光泽计测量面板的擦洗侧和未擦洗侧的LAB*值来评定去污程度，并且然后计算ΔE值。表4显示了每一种油漆的ΔE值。油漆1到3是指使用实例1到3的乳胶所制备的油漆；油漆1a、1b和1c是指使用比较实例1、2和3的乳胶所制备的油漆。
表4-唇膏污渍抗性结果
实例编号 固体(％) ΔE
油漆1 49.2 0.7
油漆1a 49.5 4.3
油漆2 48.4 0.3
油漆2a 48.0 8.2
油漆3 50.6 0.3
油漆3a 50.6 3.7
结果表明含有N2-精氨酸甲基丙烯酸酯官能化粘合剂的油漆对唇膏污渍的抗性显著改善。还发现，包括此类相对较低浓度的N2-精氨酸甲基丙烯酸酯对油漆的其它性能特性，如油漆粘度稳定性、遮盖力、耐擦洗性以及抗粘连性无不利地影响。

Claims (9)

1.一种包含聚合物颗粒的水性分散液的组合物，所述聚合物颗粒包含80到99.9重量％的甲基丙烯酸酯或丙烯酸酯单体的结构单元或其组合，0.02到4重量％的酸单体或其盐的结构单元；和0.05到3重量％的精氨酸官能化单体的结构单元，所述精氨酸官能化单体由以下结构表征：
Figure FDA0003410624140000011
其中X是NH、NHCH2CH2O、NHCH2CH2NR或NHCH2CH(OH)CH2O；并且R各自独立地是H或CH3。
2.根据权利要求1所述的组合物，其中所述精氨酸官能化单体是N2-精氨酸甲基丙烯酸酯。
3.根据权利要求2所述的组合物，其中以所述聚合物颗粒的重量计，所述聚合物颗粒包含0.1到4重量％的羧酸单体或其盐的结构单元，和0.2到2重量％的N2-精氨酸甲基丙烯酸酯的结构单元，其中所述羧酸单体是丙烯酸、甲基丙烯酸或衣康酸。
4.根据权利要求2所述的组合物，其中以所述聚合物颗粒的重量计，所述聚合物颗粒包含0.1到4重量％的硫酸单体或其盐的结构单元，和0.2到2重量％的N2-精氨酸甲基丙烯酸酯的结构单元，其中所述硫酸单体是苯乙烯磺酸或2-丙烯酰胺基-2-甲基丙烷磺酸。
5.根据权利要求2所述的组合物，其中以所述聚合物颗粒的重量计，所述聚合物颗粒包含0.2到3重量％的甲基丙烯酸磷酸乙酯或其盐。
6.根据权利要求2所述的组合物，其中所述聚合物颗粒包含0.1到4重量％的酸单体或其盐的结构，其中所述酸单体是a)羧酸单体和硫酸单体；或b)羧酸单体和磷酸单体；或c)硫酸单体和磷酸单体；或d)羧酸单体、硫酸单体以及磷酸单体。
7.根据权利要求1所述的组合物，其中所述聚合物颗粒包含甲基丙烯酸甲酯和一种或多种丙烯酸酯的结构单元，所述丙烯酸酯选自由以下组成的组：丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-丙基庚酯以及丙烯酸2-乙基己酯。
8.根据权利要求1所述的组合物，其中所述聚合物颗粒是具有橡果形态的TiO2吸附型颗粒；或球形TiO2吸附型颗粒；或TiO2非吸附型聚合物颗粒，或其组合。
9.根据权利要求1所述的组合物，所述组合物还包含TiO2和一种或多种添加剂，所述添加剂选自由以下组成的组：消泡剂、表面活性剂、分散剂、流变改性剂、杀生物剂以及中和剂。
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