CN109081913B - 缩水甘油醚烷氧基化物嵌段共聚物 - Google Patents

缩水甘油醚烷氧基化物嵌段共聚物 Download PDF

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CN109081913B
CN109081913B CN201810556336.4A CN201810556336A CN109081913B CN 109081913 B CN109081913 B CN 109081913B CN 201810556336 A CN201810556336 A CN 201810556336A CN 109081913 B CN109081913 B CN 109081913B
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E·D·道格斯
J·J·拉巴斯克
A·K·范戴克
T·张
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Rohm and Haas Co
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Abstract

本发明涉及具有以下结构I的化合物：
Figure DDA0001681437540000011
其中Ar1、Ar2；R1、m和n在本文中定义。本发明的化合物可用作水基涂料组合物、尤其水基油漆组合物中的敞开时间添加剂。

Description

缩水甘油醚烷氧基化物嵌段共聚物
背景技术
本发明涉及缩水甘油醚烷氧基化物嵌段共聚物，其可用作涂料调配物中的敞开时间添加剂。
政府法规和市场动态不断推动用于涂料调配物的零挥发性有机化合物(volatileorganic compound，VOC)。因此，不含挥发性溶剂和聚结剂的水基调配物在行业中已变得越来越受欢迎。尽管如此，油漆的性能由于这一重大变化而受到影响；其中之一为敞开时间，所述敞开时间为在这段时间内新涂覆的油漆膜可以被重新加工而不留下刷痕的时间段。在溶剂基体系中，敞开时间为约30到45分钟；在典型的水基调配物中，敞开时间约为3到5分钟。
US 8,859,684 B2公开了苯基缩水甘油醚烷氧基化物的制备，其可用作水基油漆调配物中的敞开时间添加剂。所报告的最佳敞开时间为8分钟，使用2.5重量％的添加剂。然而，由于添加剂导致最终涂层的其它性能退化，使用这种高浓度的表面活性剂以实现敞开时间的小幅增加具有有限的商业价值。因此，本领域持续需要找到一种用于水基调配物的添加剂，其优于目前可用添加剂使敞开时间明显增加，而不会使最终涂层的其它性能退化，如膜粘合强度和内聚强度、硬度、抗粘连性、早期抗起泡性、耐擦洗性和耐洗性、耐沾污性和耐擦伤性。
发明内容
本发明通过提供具有以下结构I的化合物来满足本领域的需要：
Figure BDA0001681437530000011
其中Ar1为未经取代的苯基或萘基，或经1到3个C1-C6烷基取代的苯基或萘基；并且Ar2为苯基、苯基-OCH2CH2-、苄基、萘基、萘基-CH2-或萘基-OCH2CH2-，其中Ar2的苯基或萘基部分未经取代或经1到3个C1-C6烷基取代；每个R1独立地为H或C1-C6烷基；m为1到20；并且n为1到100。本发明的化合物可用作水基涂料组合物、尤其水基油漆组合物中的敞开时间添加剂。
具体实施方式
本发明为具有以下结构I的化合物：
Figure BDA0001681437530000021
其中Ar1为未经取代的苯基或萘基，或经1到3个C1-C6烷基取代的苯基或萘基；并且Ar2为苯基、苯基-OCH2CH2-、苄基、萘基、萘基-CH2-或萘基-OCH2CH2-，其中Ar2的苯基或萘基部分未经取代或经1到3个C1-C6烷基取代；每个R1独立地为H或C1-C6-烷基；m为1到20；并且n为1到100。
本发明化合物的子类的实例由以下结构表示：
Figure BDA0001681437530000022
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Figure BDA0001681437530000031
优选地，m在1、更优选2到10、更优选6的范围内；并且n在5到40的范围内。每个R1独立地为H或C1-C6-烷基，因此氧化烯基团((OCH2CHR1)n)可以是无规或嵌段共聚物。优选地，每个R1独立地为H、甲基或乙基；更优选H或甲基；最优选每个R1为H。
可以方便地通过以下制备本发明的化合物：首先在足以制备芳基缩水甘油醚低聚物中间产物的条件下，在催化量的合适碱(如KOH)存在下使芳基醇与芳基缩水甘油醚接触，然后使中间产物与氧化烯(如环氧乙烷)在足以形成所需化合物I的条件下接触。优选地，芳基醇为苯酚、甲酚或苯氧基乙醇，并且芳基缩水甘油醚为苯基缩水甘油醚或甲苯基缩水甘油醚。
如通过基质辅助激光解吸离子质谱法(MALDI-MS)测定的，化合物的数量平均分子量(Mn)优选在300、更优选500g/mol到优选20,000、更优选到15,000、更优选到10,000、最优选到5,000g/mol范围内。
本发明化合物可用作涂料组合物的敞开时间添加剂，其包含粘合剂、流变改性剂以及任何或所有以下材料：分散剂、颜料、消泡剂、表面活性剂、溶剂、增量剂、聚结剂、杀生物剂、不透明聚合物和着色剂。
实例
实例1-苯基缩水甘油醚乙氧基化物嵌段共聚物Ia的制备
将苯酚(102.44克，1.09摩尔)、甲苯(337.83克)和KOH薄片(8.12g，90％纯)装入装备有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的2升圆底烧瓶中。将溶液在N2下加热以蒸出一部分甲苯(110g)。然后在110℃到120℃下将苯基缩水甘油醚(490.78g，3.27摩尔)历时4小时加入所得的浓缩溶液中。将混合物再搅拌2小时，并使烧瓶冷却。将一部分所得溶液(302.3g，227.9g烷氧基化物中间产物)装入锥形底2升帕尔(Parr)反应器中。将反应器密封，检查压力，用N2吹扫，然后加热到120℃。以1-2g/min的速率加入环氧乙烷(363.2g)。将混合物在120℃下保持1小时，然后冷却到60℃，之后倒出产物(652.7g)。产物用MagSil(34.8g)和水(8.9g)处理，并过滤；真空去除溶剂，产生Ia(n＝3，m＝20；523.3g)。
实例2-苯基缩水甘油醚乙氧基化物嵌段共聚物Ib的制备
向装备有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的250毫升圆底烧瓶中加入苯氧基乙醇(62.26g 0.45摩尔)和KOH薄片(1.01g，90％纯)。将溶液在N2下加热到120℃持续2小时。在120℃到125℃下历经2.5小时将苯基缩水甘油醚(203.8g，1.36摩尔)加入到所得溶液中。将混合物在120℃下搅拌过夜，然后冷却。将中间产物的一部分(240.32g)装入锥形底2升帕尔反应器中。将反应器密封，检查压力，用N2吹扫，然后加热到120℃。以1到2g/min的速率加入环氧乙烷(357.6g)。将混合物在120℃下保持过夜，然后冷却到80℃，之后倒出产物(598.4g)。将反应产物与乙酸(0.28g)混合，产生Ib(m＝3，n＝20)。
实例3-苯基缩水甘油醚乙氧基化物嵌段共聚物Ic的制备
向配有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的250毫升圆底烧瓶中加入间甲酚(48.5g，0.45摩尔)和KOH薄片(1.34g，90％活性)。将溶液在N2下加热到120℃持续2.5小时。在120℃到130℃下历经3小时将苯基缩水甘油醚(203.17g，1.35摩尔)加入到溶液中。将混合物在120℃下搅拌过夜，然后冷却。将中间产物的一部分(236.77g)装入圆锥底2升帕尔反应器中。将反应器密封，检查压力，用N2吹扫，然后加热到120℃。以1-2g/min的速率加入环氧乙烷(368.9g)。将混合物在120℃下保持过夜，然后冷却到80℃，之后倒出产物(591.38g)。将反应产物与乙酸(0.44g)混合，产生Ic(m＝3，n＝20)。
实例4-苯基缩水甘油醚乙氧基化物嵌段共聚物Id的制备
向配有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的250毫升圆底烧瓶中加入苯甲醇(44.60g，0.41摩尔)和KOH薄片(2.35g，90％纯)。将溶液在N2下加热到120℃持续1小时。在120℃到130℃下历经2小时将苯基缩水甘油醚(188.64g，1.26摩尔)加入到溶液中。将混合物在120℃下搅拌过夜，然后冷却。将中间产物的一部分(209.06g)装入锥形底2升帕尔反应器中。将反应器密封，检查压力，用N2吹扫，然后加热到120℃。以2到3g/min的速率加入环氧乙烷(322.7g)。将混合物在120℃下保持过夜，然后冷却到80℃，之后倒出产物(519.56g)。将反应产物与乙酸(0.73g)混合，产生Id(m＝3，n＝20)。
实例5-苯基缩水甘油醚乙氧基化物嵌段共聚物Ia的制备
将苯酚(62.94g，0.67摩尔)、甲苯(341.34g)和KOH薄片(4.75g，90％纯)装入装备有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的2升圆底烧瓶中。将溶液在N2下加热以蒸出一部分甲苯(82.81g)。然后在110℃到120℃下历时4小时将苯基缩水甘油醚(502.18g，3.34摩尔)加入到所得浓缩溶液中，并且搅拌混合物2小时。将一部分所得溶液(374.9g)装入圆锥底2升帕尔反应器中。将反应器密封，检查压力，用N2吹扫，然后加热到120℃。以1-2g/min的速率加入环氧乙烷(289.3g)。将混合物在120℃下保持1小时，然后冷却到60℃，之后倒出产物(650.6g)。将反应产物用乙酸(1.07g)处理，真空去除溶剂，得到Ia(m＝5，n＝20；541.6g)。
在于油漆中测试之前，将上述实例中制备的化合物以40重量％固体溶解于水中。根据表1中所示的配方制备具有和不具有示例性敞开时间添加剂的油漆调配物。以调配物的重量计，调配物中的敞开时间添加剂的浓度为1重量％。
表1-具有敞开时间添加剂的油漆调配物
材料名称 磅 加仑
RHOPLEX<sup>TM</sup>HG-706粘合剂 584.1 66.0
BYK-024消泡剂 1.0 0.1
丙二醇 4.3 0.5
TRITON<sup>TM</sup>X-100表面活性剂 4.4 0.5
水 16.7 2.0
KATHON<sup>TM</sup>LX 1.5％杀生物剂 1.5 0.2
TAMOL<sup>TM</sup>2002分散剂 2.0 0.2
氨(28％) 1.0 0.1
Ti-Pure R-746TiO<sub>2</sub> 285.0 14.7
水 20.0 2.4
Texanol聚结剂 7.9 1.0
ACRYSOL<sup>TM</sup>RM-2020E流变改性剂 20.0 2.3
ACRYSOL<sup>TM</sup>RM-725流变改性剂 3.0 0.4
BYK-024消泡剂 2.0 0.2
敞开时间添加剂(40％水溶液) 25.8 2.84
水 79 9.5
总计 1030 100
RHOPLEX、TRITON、KATHON、TAMOL和ACRYSOL都是陶氏化学公司或其附属公司的商标。
添加剂通过MALDI-MS的Mn测量
在配备有氮激光器(λ＝337nm)的Bruker Daltonics ultraflex MALDI-TOF质谱仪上获得MALDI质谱。在MALDI实验中，将20mg的2,5-二羟基苯甲酸溶解在1mL THF中作为MALDI基质。将于MeOH中的样品溶液与基质溶液以1:20的比率预混合。为了促进样品混合物中物种的离子化，将NaI加入到样品/基质混合物中。然后将0.3μl混合物样品置于样品板上并风干以进行MALDI-MS分析。在分析中选择反射模式以提高质谱的分辨率。
表2显示了在使用本发明的添加剂时对敞开时间的影响。
表2-敞开时间数据
Figure BDA0001681437530000061
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Claims (4)

1.一种具有以下结构I的化合物：
Figure FDA0003986194570000011
其中Ar1为苯基或邻甲基苯基；并且Ar2为苯基或苯基-OCH2CH2-，其中Ar2的所述苯基部分未经取代或经1到3个C1-C6烷基取代；每个R1独立地为H或CH3；
m为2到20；并且n为5到40。
2.根据权利要求1所述的化合物，具有在300到20,000g/mol范围内的数量平均分子量。
3.根据权利要求2所述的化合物，具有在500到10,000g/mol范围内的数量平均分子量，选自由以下组成的组：
Figure FDA0003986194570000012
Figure FDA0003986194570000021
/>
4.一种涂料组合物，包括根据权利要求1所述的化合物、粘合剂、流变改性剂和至少一种选自由以下组成的组的材料：分散剂、颜料、消泡剂、表面活性剂、溶剂、增量剂、聚结剂、杀生物剂、不透明聚合物和着色剂。
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