CN109134840B - 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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CN109134840B
CN109134840B CN201810575442.7A CN201810575442A CN109134840B CN 109134840 B CN109134840 B CN 109134840B CN 201810575442 A CN201810575442 A CN 201810575442A CN 109134840 B CN109134840 B CN 109134840B
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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

本发明涉及一种化合物，具有以下结构I：
Figure DDA0001686667340000011
其中Ar1、R、R1、E、m、n、x、y、p和s在本文中定义。本发明的化合物可用作水性涂料组合物、尤其是水性油漆组合物中的开放时间添加剂。

Description

缩水甘油醚烷氧基化物嵌段共聚物
技术领域
本发明涉及缩水甘油醚烷氧基化物嵌段共聚物，其可用作涂料配方中的开放时间(open time)添加剂。
背景技术
政府法规和市场动态不断推动用于涂料配方的零挥发性有机化合物(VOC)的发展。因此，不含挥发性溶剂和聚结剂的水性配方在行业中越来越受欢迎。然而，油漆的性能由于这一重大变化而被损害；其中之一为开放时间，开放时间是在这段时间内新涂覆的油漆膜可被重新加工而不留下刷痕的时间段。在溶剂型体系中，开放时间为约30至45分钟；在典型的水性配方中，开放时间约为3至5分钟。
US 8,859,684 B2公开了可用作水性油漆配方中的开放时间添加剂的苯基缩水甘油醚烷氧基化物的制备。报道的最佳开放时间为使用2.5重量％的添加剂的情况下的8分钟。然而，由于添加剂导致最终涂层的其它性能降级，因此使用此类高浓度的表面活性剂以实现开放时间的小幅增加所带来的商业价值很有限。因此，本领域需要持续寻找一种用于水性配方的添加剂，其与目前可用的添加剂相比，开放时间明显增加，同时不会使最终涂层的其它性能降级，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 BDA0001686667330000011
其中片段
Figure BDA0001686667330000021
为任选地用O原子或芳基或这两者使C2-C60直链或C3-C60支链或环状二醇、三醇或四醇官能化的结构单元，或未取代的芳族二醇、三醇或四醇的结构单元，或被1至3个C1-C6烷基取代的芳族二醇、三醇或四醇的结构单元；
每个R1独立地为H或C1-C6烷基；
E由以下结构表示：
Figure BDA0001686667330000022
m、n和q各自独立地为1至20；x、y和z各自独立地为1至50；p为0或1；s为0或1；并且
每个Ar1独立地为未取代的苯基或萘基，或被1至3个C1-C6烷基取代的苯基或萘基。
本发明的化合物可用作水性涂料组合物、尤其是水性油漆组合物中的开放时间添加剂。
具体实施方式
本发明为一种具有以下结构I的化合物：
Figure BDA0001686667330000023
其中片段
Figure BDA0001686667330000031
为任选地用O原子或芳基或这两者使C2-C60直链或C3-C60支链或环状二醇、三醇或四醇官能化的结构单元，或未取代的芳族二醇、三醇或四醇的结构单元，或被1至3个C1-C6烷基取代的芳族二醇、三醇或四醇的结构单元；
每个R1独立地为H或C1-C6烷基；
E由以下结构表示：
Figure BDA0001686667330000032
m、n和q各自独立地为1至20；x、y和z各自独立地为1至50；p为0或1；s为0或1；并且
每个Ar1独立地为未取代的苯基或萘基，或被1至3个C1-C6烷基取代的苯基或萘基。
可用于制备本发明化合物的适合二醇的实例包括C2-C20链烷二醇，如1,2-乙二醇、1,3-丙二醇、1,4-丁二醇和1,6-己二醇，以及这些二醇的烷氧基化衍生物；H-(OCH2CH(R2))b-OH类型的聚氧亚烷基二醇，其中b为2至30，优选2、3或4，更优选3；并且R2为H、甲基或乙基；芳族二醇，如1,4-苯二甲醇、儿茶酚、间苯二酚和氢醌，以及这些二醇的烷氧基化衍生物。
适合的三醇的实例包括三羟甲基丙烷、间苯三酚、偏苯三酚、邻苯三酚和甘油，以及这些三醇的烷氧基化衍生物；适合的四醇的实例为季戊四醇和苯四醇以及这些四醇的烷氧基化衍生物。
优选地，每个Ar1独立地为苯基、甲苯基或对叔丁基苯基；优选地，m和n各自独立地在从1，更优选从2至10，更优选至6，最优选至5的范围内。优选地，x和y各自独立地为从5，更优选从10至30，更优选至25。优选地，p和s都为0。
因为每个R1独立地为H或C1-C6烷基，因此氧化亚烷基((OCH2CHR1)n)可为无规或嵌段共聚物。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。
本发明的化合物的子类的实例由以下结构表示：
Figure BDA0001686667330000041
其中，对于Ia，m+n＝4，并且x+y＝30；对于Ib，m＝1，n＝1，并且x+y＝45；对于Ic，m+n＝6，并且x+y＝45；对于Id，m+n+q＝6，并且x+y+z＝40。
可如下方便地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体的条件下，在存在催化量的适合的碱如KOH的情况下，使二醇、三醇或四醇与芳基缩水甘油醚接触，然后使中间体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，多元醇为二醇，更优选三乙二醇。芳基醇优选为苯酚、对叔丁基苯酚或甲酚，并且芳基缩水甘油醚优选为苯基缩水甘油醚、对叔丁基苯酚缩水甘油醚或甲苯基缩水甘油醚。
通过基质辅助激光解吸离子质谱法(MALDI-MS)测定的化合物的数均分子量(Mn)优选地在从300g/mol，更优选从500g/mol，最优选从1000g/mol至优选20,000g/mol，更优选至15,000g/mol，更优选至10,000g/mol，最优选至5,000g/mol的范围内。
本发明的化合物可用作涂料组合物的开放时间添加剂，其包括粘合剂、流变改性剂，以及下列材料中的任何一种或全部：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
向配备有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的500mL圆底烧瓶中装入三乙二醇(61.13g，0.407摩尔)和KOH薄片(1.18g，90％纯)。在100℃下历经5小时加入苯基缩水甘油醚(247.47g，1.65摩尔)，此后将混合物冷却至室温。将所得中间体的一部分(86.7g)装入锥形底的2升Parr反应器中。将反应器密封，检查压力，用N2吹扫，然后加热至120℃。以0.2至0.3克/分钟的速率加入环氧乙烷(151.0g)。将混合物在120℃下保持1小时，然后冷却至60℃，之后倒出产物(652.7g)。将反应产物与0.18g乙酸混合以得到产物Ia(m+n＝4，并且x+y＝30)。
实例2-苯基缩水甘油醚乙氧基化物嵌段共聚物Ib的制备
向配备有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的500mL圆底烧瓶中装入三乙二醇(102.69g，0.711摩尔)和KOH薄片(2.09g，90％纯)。在95℃下历经8小时加入苯基缩水甘油醚(206.26g，1.37摩尔)，然后冷却至室温。将混合物在95℃下搅拌过夜，然后冷却。除去一部分中间体(149.5g，中间体A)，并将剩余部分重新加热至95℃。历经4小时加入第二份苯基缩水甘油醚(220.55g，1.47摩尔)。将混合物在95℃下搅拌过夜，然后冷却以除去第二中间体(333.5g，中间体B)。将中间体A的一部分(49.4g)装入锥形底的2升Parr反应器中。将反应器密封，检查压力，用N2吹扫，然后加热至120℃。以0.3至1克/分钟的速率加入环氧乙烷(218.2g)。将混合物在120℃下保持1.5小时，然后冷却至70℃，之后倒出产物(260.2g)。将反应产物与0.21g乙酸混合以形成产物Ib(m＝1，n＝1，并且x+y＝45)。
实例3-苯基缩水甘油醚乙氧基化物嵌段共聚物Ic的制备
将来自实例2的中间体B的一部分(158.8g)装入锥形底的2升Parr反应器中。将反应器密封，检查压力，用N2吹扫，然后加热至120℃。以0.3至1克/分钟的速率加入环氧乙烷(298.5g)。将混合物在120℃下保持1.5小时，然后冷却至80℃，之后倒出产物(447.0g)。将反应产物与0.17g乙酸混合以形成Ic(m+n＝6，并且x+y＝45)。
实例4-苯基缩水甘油醚乙氧基化物嵌段共聚物Id的制备
向配备有温控加热套、加料漏斗、回流/蒸馏头和顶置式搅拌器的500毫升圆底烧瓶中装入1,1,1-三(羟甲基)丙烷(TMP，59.59g，0.444摩尔)，将其加热至70℃，然后加入KOH薄片(2.75g，90％纯)。将溶液加热至95℃，随后历经4小时加入苯基缩水甘油醚(400.0g，2.66摩尔)。将混合物在90℃下搅拌过夜，然后冷却。将此中间体的一部分(221.9g)装入锥形底的2升Parr反应器中。将反应器密封，检查压力，用N2吹扫，然后加热至120℃。以1至2克/分钟的速率加入环氧乙烷(378.0g)。将混合物在120℃下保持1.5小时，然后冷却至80℃，之后倒出产物(561.3g)。将反应产物与1.5g乙酸混合以形成Id(m+n+q＝6，并且x+y+z＝40)。
通过MALDI-MS测量添加剂的Mn
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的THF中以作为MALDI基质。将于MeOH中的样品溶液与基质溶液以1:20的比例预混合。为了促进样品混合物中的物质的离子化，将NaI加入到样品/基质混合物中。然后将0.3μl的混合物样品置于样品板上并风干以进行MALDI-MS分析。在分析中选择反射器(reflectron)模式以提高质谱的分辨率。
涂料配方
根据表1制备具有和不具有开放时间添加剂的油漆配方。
表1-具有开放时间添加剂的油漆配方
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
开放时间添加剂(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(The Dow ChemicalCompany)或其附属公司的商标。
表2显示了在使用本发明的添加剂时对开放时间的影响。
表2-开放时间数据
Figure BDA0001686667330000071
数据表明含有本发明添加剂的涂料配方的开放时间显著增加。

Claims (9)

1.一种化合物，具有以下结构I：
Figure FDA0003922862560000011
其中片段
Figure FDA0003922862560000012
为任选地用O原子或芳基或这两者使C2-C60直链或C3-C60支链或环状二醇、三醇或四醇官能化的结构单元，或未取代的芳族二醇、三醇或四醇的结构单元，或被1至3个C1-C6烷基取代的芳族二醇、三醇或四醇的结构单元；
每个R1独立地为H或C1-C6烷基；
E由以下结构表示：
Figure FDA0003922862560000013
m、n和q各自独立地为1至20；x、y和z各自独立地为1至50；p为0或1；s为0或1；并且
每个Ar1独立地为未取代的苯基或萘基，或被1至3个C1-C6烷基取代的苯基或萘基。
2.根据权利要求1所述的化合物，其中p为0；s为0；每个R1独立地为H或CH3；m和n各自独立地在1至10的范围内；并且x和y各自独立地在5至30的范围内。
3.根据权利要求1所述的化合物，其中所述片段：
Figure FDA0003922862560000021
为以下醇的结构单元：a)二醇，其为C2-C20链烷二醇或其烷氧基化衍生物；或H-(OCH2CH(R2))b-OH类型的聚氧亚烷基二醇，其中b为2至30，并且R2为H、甲基或乙基；或芳族二醇或其烷氧基化衍生物；或b)三醇或其烷氧基化衍生物；或c)四醇或其烷氧基化衍生物。
4.根据权利要求2所述的化合物，其中所述片段：
Figure FDA0003922862560000022
为H-(OCH2CH2)b-OH类型的聚氧亚烷基二醇的结构单元，其中b为2至30。
5.根据权利要求4所述的化合物，具有在1000克/摩尔至5000克/摩尔的范围内的Mn；其中每个R1为H；并且b为2、3或4。
6.根据权利要求5所述的化合物，其中b为3。
7.根据权利要求1所述的化合物，由以下结构表示：
Figure FDA0003922862560000031
其中m+n＝4，并且x+y＝30；或m＝1，n＝1，并且x+y＝45；或m+n＝6，并且x+y＝45。
8.根据权利要求1所述的化合物，由以下结构表示：
Figure FDA0003922862560000032
其中m+n+q＝6，并且x+y+z＝40。
9.一种涂料组合物，包含根据权利要求1至8中任一项所述的化合物、粘合剂、流变改性剂，以及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、杀生物剂和不透明聚合物。
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