CN112778485A - 一种梳型聚氨酯超分散剂的制备方法、分散剂及其应用 - Google Patents
一种梳型聚氨酯超分散剂的制备方法、分散剂及其应用 Download PDFInfo
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- CN112778485A CN112778485A CN202110171883.2A CN202110171883A CN112778485A CN 112778485 A CN112778485 A CN 112778485A CN 202110171883 A CN202110171883 A CN 202110171883A CN 112778485 A CN112778485 A CN 112778485A
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- hyperdispersant
- polyurethane
- comb
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- diisocyanate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- Polyurethanes Or Polyureas (AREA)
Abstract
本发明属于高分子分散剂技术领域，具体公开了一种梳型聚氨酯超分散剂的制备方法、分散剂及其应用，所述制备方法是使单端伯氨基聚醚与至少二倍当量的烷基缩水甘油醚反应，生成含二个羟基的叔胺基聚醚中间体，然后将所述叔胺基聚醚中间体加入到二异氰酸酯与二元醇或二元聚醚的预聚物中扩链，最后加入含有芳基双活性基团的组分，制得梳型聚氨酯超分散剂。本发明利用烷基缩水甘油醚与单端伯氨基聚醚反应形成二羟基中间体，可将聚醚单元胺完全转化，有效避免副产物的产生，得到具有优异且稳定的分散性能的梳型聚氨酯超分散剂。此外，本发明可制备得到适用于水性体系、溶剂型体系或同时适用于水性和溶剂型体系的疏型聚氨酯超分散剂。
Description
技术领域
本发明属于高分子分散剂技术领域，具体涉及一种梳型聚氨酯超分散剂的制备方法、分散剂及其应用。
背景技术
分散剂是促使物料颗粒均匀分散于介质中的物质，高分子型分散剂，又称为多功能颜料分散剂，是最为常用的分散剂，分为多己内多酯多元醇-多乙烯亚胺嵌段共聚物型分散剂、丙烯酸酯高分子型分散剂、聚氨酯或聚酯型高分子分散剂等，它们的高分子链段能够与介质分子缠绕，又具有多个锚锭基团可牢固结合在颜料粒子表面，因此其对于介质中颗粒的贮存稳定性较传统的低分子量分散剂有显著优势。梳型分散剂是新一代的高分子分散剂，除了高分子链段和锚固基团外，还具有梳型支链，即溶剂化链，显著提高了溶剂化能力和空间位阻，避免分散颗粒的吸引团聚，分散效果更佳。
梳型分散剂的制备一般都比较复杂，容易有副产物的产生，导致无法达到预期的使用效果。例如，专利WO2016/077147公开了一种梳型聚氨酯分散剂，由草酰胺二醇与二异氰酸酯反应形成，核心工艺为草酸二乙酯与二乙醇胺(DEA)反应生成4-羟基乙基-2,3-二羰基吗啉(HEMD)，然后HEMD与聚醚单元胺反应制成草酰胺二醇，草酰胺二醇与二异氰酸酯反应合成分子量约13 000-40 000的梳型聚氨酯分散剂；该专利的不足之处在于草酰胺二醇的产率在89.7-95.6%，未转化的聚醚单元胺一端是氨基，另一端是羟基，会与异氰酸酯反应产生副产物，而非梳型的高分子聚氨酯，影响产物纯度。
发明内容
为解决上述问题，本发明提供了一种梳型聚氨酯超分散剂的制备方法。该法可将聚醚单元胺完全转化，有效避免副产物的产生，得到具有优异且稳定的分散性能的梳型聚氨酯超分散剂。
为达到上述目的，本发明采用的具体技术方案如下：
一种梳型聚氨酯超分散剂的制备方法，是使单端伯氨基聚醚与至少二倍当量（即二倍摩尔量）的烷基缩水甘油醚反应，生成含二个羟基的叔胺基聚醚中间体，然后将所述叔胺基聚醚中间体加入到二异氰酸酯与二元醇或二元聚醚的预聚物中进行扩链反应，最后加入含有芳基双活性基团的组分，制得梳型聚氨酯超分散剂。所述含有芳基双活性基团的组分中活性基团是指能够与异氰酸酯基反应且能锚固在颜料颗粒表面的基团，如氨基、羧基、羟基等。本发明梳型聚氨酯超分散剂的亲油亲水性可由单端伯氨基聚醚的HLB值调节控制，所述单端伯氨基聚醚可以是HLB值较高的聚氧乙烯醚胺、HLB值较低的聚氧丙烯醚胺等。
优选的，所述单端伯氨基聚醚分子式如下：
其中，R为H或CH3，X为1-50，Y为3-40。上述结构式中，只要调节乙氧单元和丙氧单元的数量，即可实现梳型聚氨酯超分散剂的亲水亲油性调节，增加丙氧单元数量，亲油性提升，增加乙氧单元数量，亲水性提升。
进一步的，所述单端伯氨基聚醚的分子量为600-5000。分子量过小，溶剂化能力和空间位阻不足，分子量过大，易产生分散剂从分散颗粒表面上脱附的现象。
优选的，所述烷基缩水甘油醚分子式如下：
其中，R1是C1-C12的烷基或不饱和烃基。
优选的，所述含有芳基双活性基团的组分为氨基苯磺酸和/或羟基萘甲酸。
优选的，所述二异氰酸酯为二苯基甲烷二异氰酸酯（简称MDI）、甲苯二异氰酸酯（简称TDI）、六亚甲基二异氰酸酯（简称HDI）、2,2,4-三甲基己烷二异氰酸酯（简称TMHDI）、苯二亚甲基二异氰酸酯（简称XDI）、多苯基甲烷多异氰酸酯（简称PAPI）、 异佛尔酮二异氰酸酯（简称IPDI）、 间1,4-甲基苯亚甲基二异氰酸酯（简称m-TMXDI）、对1,4-甲基苯亚甲基二异氰酸酯（简称p-TMXDI）中的一种或多种。
优选的，所述梳型聚氨酯超分散剂的分子量为10000-60000。
进一步的，所述梳型聚氨酯超分散剂的分子量为15000-30000。
本发明还提供了采用上述梳型聚氨酯超分散剂的制备方法制得的梳型聚氨酯超分散剂，所述梳型聚氨酯超分散剂以二异氰酸酯与二元醇/二元聚醚聚合物链段为主链、氨基聚醚链段为溶剂化梳型侧链，芳基双活性基团为锚固基团。
本发明上述梳型聚氨酯超分散剂可应用于制备油墨或涂料，可将颜料颗粒快速均匀地分散于油墨或涂料中，使油墨或涂料具备良好的分散效果和视觉效果。
本发明利用烷基缩水甘油醚与单端伯氨基聚醚反应形成二羟基中间体，对聚氨酯分散剂预聚物进行扩链，制成一种新的梳型聚氨酯超分散剂。以单端伯氨基聚醚作为聚醚单元胺，其伯胺能在无催化剂条件下与烷基缩水甘油醚的环氧反应生成含活性羟基的仲胺，仲胺与环氧可继续反应生成含双活性羟基的叔胺，反应式如下：
这种方法可以将单端伯氨基聚醚完全转化，克服现有技术中聚醚单元胺残留导致的非理性结构副产物的产生，有效提高产物纯度。
本发明具有以下有益效果：
1、以单端伯氨基聚醚作为聚醚单元胺，将其与烷基缩水甘油醚反应，能够使单端伯氨基聚醚够完全转化，有效减少了反应副产物的产生。
2、本发明梳型聚氨酯超分散剂主链上的芳基双活性基团稳定地锚固在颜料等固体颗粒表面，聚醚侧链提供溶剂化和空间位阻能力，有效避免分散颗粒的吸引团聚，分散效果好，且分散剂分子量大，稳定性好，颜料等固体颗粒不易沉降，利于长期贮存。
3、通过调节单端伯氨基聚醚中乙氧单元和丙氧单元的组成比例，即可实现梳型聚氨酯超分散剂的亲水亲油性调节，本发明可制备得到适用于水性体系、溶剂型体系或同时适用于水性和溶剂型体系的疏型聚氨酯超分散剂。
具体实施方式
以下结合具体实施例对本发明进行进一步的说明。
实施例1：水性梳型聚氨酯超分散剂的制备
S1.中间体A合成
称取单端伯氨基聚醚（分子量1000，具有3个丙氧单元和19个乙氧单元）300克，加入已用分子筛脱水的丙二醇乙醚醋酸酯250克，80℃下搅拌滴加78克丁基缩水甘油醚，保温反应6小时，得到中间体A；
S2.扩链反应
所述扩链反应的主要原料添加配方如下表1所示：
表1
操作时，将2500ml规格三口烧瓶置于冰水浴中，先加入已用分子筛脱水的聚丙二醇160克，60℃下搅拌滴加257.22克液化MDI(Desmodue PC)，然后加入有机铋催化剂0.5克，反应1小时后滴加378克中间体A，升温至80℃反应4h，再融溶滴加34.8克对氨基苯磺酸反应4小时，加入578克去离子水，得到产物。产物为浅黄色透明流体，固体含量50%。
实施例2：油性梳型聚氨酯超分散剂的制备
S1.中间体B合成
称取单端伯氨基聚醚（分子量1000，壬基酚聚氧丙烯醚胺）700克，加入已用分子筛脱水的丙二醇乙醚醋酸酯700克，80℃下搅拌滴加182克丁基缩水甘油醚，保温反应6小时，得到中间体B；
S2.扩链反应
所述扩链反应的主要原料添加配方如下表2所示：
表2
操作时，将5000ml规格三口烧瓶置于冰水浴中，先加入已用分子筛脱水的丙二醇乙醚醋酸酯1050克，再在搅拌下缓慢滴加514.4克TDI(Desmodue T80)以及320克脱水聚乙二醇，升温至80℃反应2h，然后滴加1064克中间体B反应30min，加入5克有机铋催化剂后升温至90℃继续反应4h，熔融滴加对氨基苯磺酸34.7克，反应3h，得到产物。产物为浅黄色透明流体，固体含量50%。
实施例3：油水通用梳型聚氨酯超分散剂的制备
S1.中间体C合成
称取单端伯氨基聚醚（分子量2000，具有10个丙氧单元和31个乙氧单元）1400克，加入已用分子筛脱水的丙二醇乙醚醋酸酯800克，80℃下搅拌滴加182克丁基缩水甘油醚，保温反应4小时，得到中间体C；
S2.扩链反应
所述扩链反应的主要原料添加配方如下表3所示：
表3
操作时，将5000ml规格三口烧瓶置于水浴中，先加入已用分子筛脱水的丙二醇乙醚醋酸酯700克，再加入514.5克液化MDI（Desmodue PC），滴加94.5克己二醇和200克丙二醇乙醚醋酸酯溶液，升温至80℃反应2h，再滴加中间体C反应30min，加入5克有机铋催化剂后升温至90℃继续反应1h，滴加37.4克2-羟基-6-萘甲酸和124.6克丙二醇乙醚醋酸酯溶液反应1h，得到产物。产物为浅黄色透明流体，固体含量55%。
对比试验1：炭黑颜料分散试验
试验过程如下：
一、炭黑颜料浆制备及评价
以丙二醇甲醚为溶剂，加入德固赛FW-200炭黑，分别将实施例2、实施例3、德国BASF EFKA-4050作为分散剂加入，制成三个油性分散体系（各个分散体系中各组分添加的重量份如下表4所示）；在每个分散体系中加入1mm粒径锆珠，曲轴转速660rpm快手研磨1小时，然后纱网过滤掉锆珠，得到分散液A、B、C三种炭黑颜料浆。
测试分散液A、B、C的刮板细度及旋转粘度，其中刮板细度按照GB/T 1724-1979 涂料细度测定法测定，旋转粘度按照ASTM D2196-2018《旋转粘度计对非牛顿材料流变特性的标准测试方法》测定。结果如下表4所示，可以看出，本发明实施例2和实施例3分散剂对于炭黑颜料的分散效果可达到甚至略优于对比分散剂德国BASF EFKA-4050的水平，制成的炭黑颜料浆流动性更好。
表4 炭黑颜料浆配比及评价结果
二、双组分聚氨酯涂料中的应用评价
将分散液A、B、C用于黑色聚氨酯双组分涂料的制备，所述黑色聚氨酯双组分涂料的原料包括60%羟基丙烯酸树脂、二甲苯、醋酸丁酯、炭黑颜料浆、BYK-323流平剂、TEGOAirex932消泡剂，各组分添加的质量份如下表5所示。将22A-75PXHDI固化剂（六亚甲基二异氰酸酯）与经脱水处理的醋酸丁酯以1：1比例混合均匀，作为上述涂料组分的固化剂，使用配比为涂料组分：固化剂：稀释剂=1：1：0.3，然后用槽深为150um的块状涂布器涂布于厚度为3mm，长宽为150mmx100mm的玻璃板上，按GB/T 9754-2007《不含金属颜料的色漆漆膜的20°、60°或 85°镜面光泽的测定》制膜保养并测定60°光泽。采用100微米涂膜器在LENETA黑白卡纸上涂膜，用Xrite MA-68Ⅱ分光光度计按照DIN6274标准测试计算黑度。
黑色聚氨酯双组分涂料涂膜的性能测试结果如下表5所示，可以看到，本发明实施例2和实施例3分散剂制成的分散液应用于双组分聚氨酯涂料，视觉效果好，可达到对比分散剂德国BASF EFKA-4050的水平。
表5 双组分聚氨酯涂料配比及应用评价结果
对比试验2：大红颜料分散试验
试验过程如下：
一、颜料红浆制备及评价
以去离子水为溶剂，加入颜料红122，分别将实施例1、实施例3、德国赢创ZetaSperse3100作为分散剂加入，制成三个水性分散体系（各个分散体系中各组分添加的重量份如下表6所示）；在每个分散体系中加入1mm粒径锆珠，曲轴转速660rpm快手研磨1小时，然后纱网过滤掉锆珠，得到分散液D、E、F三种颜料红浆。
测试分散液D、E、F的刮板细度及旋转粘度，刮板细度和旋转粘度测试方法同对比试验1。结果如下表6所示，可以看出，本发明实施例1和实施例3分散剂相对于颜料红的分散效果可达到甚至略优于对比分散剂德国赢创ZetaSperse3100的水平，制成的颜料红浆流动性更好。
表6 颜料红浆配比及评价结果
二、水性高光泽油墨中的应用评价
将分散液D、E、F用于水性高光泽油墨的制备，所述水性高光泽油墨的原料包括60℃热水、碱溶性丙烯酸树脂、二甲基乙醇胺、异构13醇聚氧乙烯醚、聚酮附着力促进剂、颜料红浆、抗磨剂，各组分添加的质量份如下表7所示，将上述组分混匀搅拌混匀后即制得水性高光泽油墨。
对制得的红色水性高光泽油墨进行着色力、刮板细度及光泽度测量。具体的，光泽度测量方法参照GB/T 8941-2013《纸和纸板镜面光泽度的测定》，本实验采用75型光泽度仪进行测量，牛皮纸印刷后，使用75°角测量表层的光泽度。着色力测量方法如下：在天平中分别称取1g标准红墨和10g白墨，并用同样的方法称取相同比例的自制红墨和白墨，用调墨刀充分调匀；随后将调匀的油墨冲淡，吸取试样放置于刮样纸左上方，取墨样刮于右上方；用刮片自上而下刮80mm到100mm长。观察试样于标样的墨色，通过添加白墨改变试样直至冲淡样与标样达到一致，通过以下公式得出试样着色力：
S=D/C×100%；
其中，S为着色力百分比（%），D为冲淡试样白墨用量（g），C为冲淡标样白墨用量（g）。
红色水性高光泽油墨的性能测试结果如下表7所示，可以看到，本发明实施例1和实施例3分散剂制成的分散液应用于水性高光泽油墨，在分散效果以及制成的油墨的着色力、光泽度上均可达到对比分散剂德国赢创ZetaSperse3100的水平。
表7 水性高光泽油墨配比及应用评价结果
综上，本发明可制得适用于水性体系、溶剂型体系或同时适用于水性和溶剂型体系的疏型聚氨酯超分散剂，每一种对于颜料颗粒都具有极佳的分散效果，并且在涂料或者油墨中的实际应用效果可达到国外优质分散剂的水平。
本具体实施方式仅仅是对本发明的解释，并不是对本发明的限制，本领域技术人员在阅读了本发明的说明书之后所做的任何改变，只要在本发明权利要求书的范围内，都将受到专利法的保护。
Claims (10)
1.一种梳型聚氨酯超分散剂的制备方法，其特征在于：是使单端伯氨基聚醚与至少二倍当量的烷基缩水甘油醚反应，生成含二个羟基的叔胺基聚醚中间体，然后将所述叔胺基聚醚中间体加入到二异氰酸酯与二元醇或二元聚醚的预聚物中进行扩链，最后加入含有芳基双活性基团的组分，制得梳型聚氨酯超分散剂。
2.根据权利要求1所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述单端伯氨基聚醚分子式如下：
其中，R为H或CH3，X为1-50，Y为3-40。
3.根据权利要求2所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述单端伯氨基聚醚的分子量为600-5000。
4.根据权利要求1所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述烷基缩水甘油醚分子式如下：
其中，R1是C1-C12的烷基或不饱和烃基。
5.根据权利要求1所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述含有芳基双活性基团的组分为氨基苯磺酸和/或羟基萘甲酸。
6.根据权利要求1所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述二异氰酸酯为二苯基甲烷二异氰酸酯、甲苯二异氰酸酯、六亚甲基二异氰酸酯、2,2,4-三甲基己烷二异氰酸酯、苯二亚甲基二异氰酸酯、多苯基甲烷多异氰酸酯、 异佛尔酮二异氰酸酯、间或对1,4-甲基苯亚甲基二异氰酸酯中的一种或多种。
7.根据权利要求1所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述梳型聚氨酯超分散剂的分子量为10000-60000。
8.根据权利要求7所述的梳型聚氨酯超分散剂的制备方法，其特征在于：所述梳型聚氨酯超分散剂的分子量为15000-30000。
9.采用权利要求1-8任一项所述的梳型聚氨酯超分散剂的制备方法制备得到的梳型聚氨酯超分散剂。
10.权利要求9所述的梳型聚氨酯超分散剂在制备油墨或涂料中的应用。
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