CN107868185B - 氨基酸结构单元官能化乳胶 - Google Patents

氨基酸结构单元官能化乳胶 Download PDF

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CN107868185B
CN107868185B CN201710833106.3A CN201710833106A CN107868185B CN 107868185 B CN107868185 B CN 107868185B CN 201710833106 A CN201710833106 A CN 201710833106A CN 107868185 B CN107868185 B CN 107868185B
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polymer particles
acid monomer
methacrylate
structural units
composition
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CN107868185A (zh
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A·S·布朗奈尔
M·塞西欧萨姆
Y·龚
T·J·贝尔
J·C·勃林
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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。本发明的组合物适用于改善涂料组合物对唇膏污渍的抗性。

Description

氨基酸结构单元官能化乳胶
背景技术
本发明涉及包含氨基酸结构单元(如6-赖氨酸甲基丙烯酸酯)官能化聚合物颗粒(即，乳胶)的稳定水性分散液的组合物。本发明的组合物适用于包覆配制物。
使涂料级乳液聚合物配制成的涂料实现卓越的抗污性和/或污渍阻隔性对于配制者来说是一种持续的挑战，部分原因在于其往往难以在抗污性改善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。为了加入问题的复杂性，疏水性抗污性的改善往往与对亲水性抗污性的损害相关。
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，但是也会有损于抗水性和亲水性抗污性，且加剧了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；尽管如此，已知PEM在造漆工艺期间加剧粗粒形成。另外，在某些配方原材料(如某些类型的绿坡缕石或膨润土粘土)的存在下，含有PEM的聚合物往往展现有限的相容性。
丙烯酸乙酯(EA)官能化聚合物颗粒尤其抗唇膏污渍，但为了看到这种作用，往往需要EA的浓度超过总乳胶颗粒组成的20％，由此限制了其它单体选择。此外，EA具有非常低的气味临界值，因此需要广泛地消除残余单体且有时成本高。
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)可能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组合物解决了所属领域中的一个需求，所述组合物包含聚合物颗粒的稳定水性分散液，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％的可聚合氨基酸的结构单元，所述可聚合氨基酸具有以下结构：
Figure BDA0001409162470000011
其中X是NH、NHCH2CH2O或NHCH2CH(OH)CH2O；且R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稳定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％的可聚合氨基酸的结构单元，所述可聚合氨基酸具有以下结构：
Figure BDA0001409162470000021
其中X是NH、NHCH2CH2O或NHCH2CH(OH)CH2O；且R是H或CH3。
优选的是，X是NH且R是CH3。
如本文所用，术语“聚合物颗粒的稳定水性分散液”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，6-赖氨酸甲基丙烯酸酯(也称为N6-(2-甲基-1-侧氧基-2-丙烯-1-基)-L-赖氨酸)的结构单元说明如下：
Figure BDA0001409162470000022
6-赖氨酸甲基丙烯酸酯的结构单元
其中虚线表示连接到聚合物主链的点。优选的是，可聚合氨基酸的结构单元在聚合物颗粒中(优选6-赖氨酸甲基丙烯酸酯的结构单元在聚合物颗粒中)的浓度以聚合物颗粒重量计是0.1重量％，更优选0.2重量％，且最优选0.25重量％，到2重量％，更优选到1重量％且最优选到0.75重量％。
可聚合胺基酸的其它实例包括N6-(2-羟基-3-(甲基丙烯酰氧基)丙基)-L-赖氨酸：
Figure BDA0001409162470000023
N6-(2-羟基-3-(甲基丙烯酰氧基)丙基)-L-赖氨酸
其可以通过赖氨酸和甲基丙烯酸缩水甘油酯的反应制备；以及N6-(2-(甲基丙烯酰氧基)乙基)-L-赖氨酸：
Figure BDA0001409162470000031
N6-(2-(甲基丙烯酰氧基)乙基)-L-赖氨酸
其可以通过赖氨酸与甲基丙烯酸羟乙酯的缩合制备。
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。适合的酸单体类别包括羧酸、硫酸、磷酸单体。羧酸单体和其盐的实例包括丙烯酸、甲基丙烯酸以及衣康酸(itaconic acid)和其盐；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、乙烯基磺酸以及2-丙烯酰胺基-2-甲基丙磺酸和其盐。
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烷酯或甲基丙烯酸羟烷酯的磷酸酯，包括甲基丙烯酸磷酸乙酯(PEM)和甲基丙烯酸磷酸丙酯。PEM是尤其优选的磷酸单体，由以下结构表示：
Figure BDA0001409162470000032
其中R是H或
Figure BDA0001409162470000033
优选的是，酸单体结构单元的浓度以聚合物颗粒重量计是在0.05重量％(更优选0.1重量％且最优选0.3重量％)到优选6重量％(更优选4重量％且更优选2重量％)的范围内。酸单体还可以是酸单体的组合，例如磷酸单体，以聚合物颗粒重量计，其浓度优选在0.1重量％(更优选0.2重量％且最优选0.5重量％)到优选5重量％(更优选3重量％且最优选2重量％)的范围内；以及羧酸单体，以聚合物颗粒重量计，其浓度优选在0.1重量％(更优选0.2重量％且最优选0.5重量％)到优选4重量％(更优选2.5重量％)的范围内。
聚合物颗粒优选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”是指聚合物颗粒(包括晶种聚合物颗粒)，以聚合物颗粒重量计，其包含至少25重量％的甲基丙烯酸酯或丙烯酸酯单体结构单元或其组合。优选的是，丙烯酸类聚合物颗粒包含50重量％(更优选80重量％且最优选90重量％)到99.9重量％(更优选98重量％且最优选96重量％)的丙烯酸酯或甲基丙烯酸酯单体结构单元或其组合。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多烯系不饱和单体(如二乙烯基苯或甲基丙烯酸烯丙酯)的结构单元，且还可以包含其它单体(如苯乙烯和乙酸乙烯酯)的结构单元。
聚合物颗粒的形态并非关键。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，其中核心部分从聚合物颗粒的壳体部分凸出；且其可以是颜料吸附(例如TiO2吸附)型聚合物颗粒，但不必定是。
本发明的组合物进一步有利地包括颜料，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、杀生物剂和中和剂。已经惊人地发现，由本发明组合物形成的涂料(尤其油漆)对唇膏污渍展现明显的抗性，而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-未经赖氨酸甲基丙烯酸酯官能化的双形态吸附型乳胶的制备
A.核心(预形体)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)与甲基丙烯酸(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℃且启动搅拌。然后添加一部分ME1(70g)，随后快速添加过硫酸钠(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，以线性方式历经40分钟分别添加ME1的其余部分、随后为冲洗液(25g)和过硫酸钠(0.64g)溶解于去离子水(50g)中的引发剂溶液。ME1进料完成之后，使烧瓶的内含物在85℃下保持10分钟，之后完成共进料且然后使烧瓶的内含物在85℃下再保持10分钟。使烧瓶的内含物冷却到室温且用氢氧化铵的稀释溶液中和到pH 3。使用Brookhaven BI 90Plus颗粒分析仪测量的粒度是60-75nm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入口和回流冷凝器的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℃且启动搅拌。然后添加一部分ME2(75g，总单体的3.5％)，随后快速添加过硫酸铵(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，然后添加得自步骤A的一部分预形体(212.5g，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，各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℃的温度下。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，然后添加至烧瓶中。
使烧瓶的内含物冷却到65℃且向烧瓶中添加催化剂/活化剂对以减少残余单体。添加TERGITOLTM15-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pH 9。使用Brookhaven BI 90Plus颗粒分析仪测量的粒度是122nm且固体是49.5％。
比较实例2-未经赖氨酸甲基丙烯酸酯官能化的双阶段球形吸附型乳胶的制备
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)、甲基丙烯酸磷酸乙基酯(30.6g，60％活性)和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)和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入口和回流冷凝器的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℃且启动搅拌。然后添加一部分ME1(105g)，随后快速添加过硫酸铵(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。ME1添加完之后，用去离子水(25g)冲洗含有ME1的容器，然后添加至烧瓶中，且使烧瓶的内含物在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。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)的溶液分别添加到烧瓶中。所有添加完成时，用去离子水(25g)冲洗含有ME2的容器，然后添加至烧瓶中。
使烧瓶的内含物冷却到70℃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pH 9.3。使用Brookhaven BI 90Plus颗粒分析仪测量的粒度是109nm且固体是48.0％。
比较实例3-未经赖氨酸甲基丙烯酸酯官能化的球形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)和甲基丙烯酸(19.52g)混合来制备单体乳液。
向装备有桨式搅拌器、温度计、N2入口和回流冷凝器的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)，和碳酸钠(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℃且启动搅拌。然后添加一部分单体乳液(59g)，随后快速添加过硫酸铵(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，向烧瓶中分别添加单体乳液的其余部分和含有溶解于去离子水(99g)中的过硫酸铵(1.04g)的溶液，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，然后添加至烧瓶中，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℃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pH 8.5。使用Brookhaven BI 90Plus颗粒分析仪测量的粒度是140nm且固体是50.6％。
实例1-赖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，例外之处是在B部分中，将甲基丙烯酸甲酯的量减少17g至780.33g且将赖氨酸甲基丙烯酸酯(68g，12.5％活性，8.5g 6-异构体)添加至ME2混合物中。可以如IP.com第000201337号针对N-甲基丙烯酰基-L-赖氨酸共聚物所述来制备赖氨酸甲基丙烯酸酯。
实例2-赖氨酸甲基丙烯酸酯官能化的双阶段球形吸附型乳胶的制备
基本上如比较实例2中所述制备乳胶，例外之处是将ME2中的甲基丙烯酸甲酯的量减少8.5g至440.98g且将赖氨酸甲基丙烯酸酯(34g，12.5％活性，4.3g 6-异构体)添加至ME2混合物中。
实例3-赖氨酸甲基丙烯酸酯官能化的球形非吸附型乳胶的制备
基本上如比较实例3中所述制备乳胶，例外之处是将单体混合物中的甲基丙烯酸甲酯的量减少9.8g至967.73g且将赖氨酸甲基丙烯酸酯(39.2g，12.5％活性，4.9g的6-异构体)添加至单体乳液混合物中。
表1展现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染抗性测试。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ASP 170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 BDA0001409162470000071
Figure BDA0001409162470000081
表3展现了制备另一种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染抗性测试。粘合剂是指由实例3和比较实例3制备的乳胶。
表2-实例3和比较实例3的包括粘合剂的油漆配制物
lbs gal
研磨剂
水 40.00 4.79
Byk-022 1.00 0.12
Surfonyl CT-111 3.28 0.41
Tamol 2011 8.76 0.96
Ti-Pure R-746 314.25 16.17
松弛剂
粘合剂3 538.88 60.69
Tamol 2011 11.28 1.24
BYK-024 4.99 0.59
Texanol 27.27 3.44
添加研磨剂且将pH调节到8.6
RM-2020 26.22 3.01
RM-8W 2.70 0.31
水 79.00 9.46
将KU调节到95-100，ICI调节到1至1.2，pH调节到～8.6
总计 1046.34 99.97
表3比较了实例和比较性中间实例的粒度和pH值；PS是指聚合物颗粒的平均粒度。
表3-粒度和pH比较
实例编号 PS(nm) pH
1 126 9.1
比较例1 122 9.0
2 110 9.3
比较例2 109 9.4
3 139 8.5
比较例3 140 8.5
结果表明对胶体稳定性无明显有害的影响且6-赖氨酸甲基丙烯酸酯官能基包含于聚合物颗粒中未引起粒度控制减弱。
污渍测试程序(根据ASTM方法D4828改编)
使用7密耳(湿)陶氏涂抹器将测试油漆浇注于黑色乙烯卡片上，且靠近测试油漆浇注对照油漆。在77oF(25℃)下、在50％相对湿度下干燥油漆七天。跨越测试板对二分之一英寸截面作出标记且均匀地涂覆唇膏以填补测试区域。允许污渍浸泡约2小时。将3"×4"海绵浸泡于自来水中且挤压直到没有更多的水从海绵中滴出。然后将海绵附着到1kg磨耗舟上且将10mL充分混合的Leneta标准化非磨耗洗涤介质和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舟，将面板洗涤100个循环。用水充分地冲洗面板且让其干燥；使用BYK色差仪45/0光泽计评定去污程度，以测量面板的洗涤侧和未洗涤侧的LAB*值，且然后计算ΔE值。表4展现了每一种油漆的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 49.1 1.0
油漆1a 49.5 4.1
油漆2 48.0 2.2
油漆2a 48.0 7.6
油漆3 50.4 1.6
油漆3a 50.6 17.8
结果表明含有赖氨酸甲基丙烯酸酯官能化粘合剂的油漆的唇膏污渍抗性显著改善。还已经发现，包含这种相对较低浓度的6-赖氨酸甲基丙烯酸酯对油漆的其它性能特性未产生不利影响。

Claims (8)

1.一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％的可聚合氨基酸结构单元，所述可聚合氨基酸具有以下结构：
Figure FDA0003307796330000011
其中X是NH、NHCH2CH2O或NHCH2CH(OH)CH2O；且R是H或CH3；并且
其中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或其组合的结构单元。
2.根据权利要求1所述的组合物，其中所述可聚合氨基酸是6-赖氨酸甲基丙烯酸酯。
3.根据权利要求2所述的组合物，其中按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6-赖氨酸甲基丙烯酸酯结构单元，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，其中按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6-赖氨酸甲基丙烯酸酯结构单元，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，其中按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单元，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、硫酸单体和磷酸单体。
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选自由以下组成的群组的丙烯酸酯的结构单元：丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-丙基庚酯和丙烯酸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。
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