CN106892985A - 麦芽糊精的二苯乙烯基或三苯乙烯基苯酚单缩水甘油醚加合物 - Google Patents
麦芽糊精的二苯乙烯基或三苯乙烯基苯酚单缩水甘油醚加合物 Download PDFInfo
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Abstract
本发明涉及一种化合物,其为式I化合物的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物:
Description
技术领域
本发明涉及麦芽糊精的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物和其制备。此化合物可作为添加剂,用来改善涂料调配物中的开放时间。
背景技术
政府法规和市场运动不断地推动在涂料调配物中使用零挥发性有机化合物(VOC)。因此,不含挥发性溶剂和聚结剂的水性调配物在行业内已越来越受欢迎。然而,由于这种突变,涂料的性能做出了妥协;这些性能中有开放时间,其为新涂油漆膜可以返工而不留刷痕的一段时间。在溶剂型系统中,开放时间大约是30到45分钟;在典型的水性调配物中,开放时间大约是3到5分钟。因此,现有技术中存在如下需求:找到用于水性调配物的添加剂,与现有添加剂相比,所述添加剂增加开放时间而不降低最终涂层的其他性能,诸如膜粘合性和粘结强度、硬度、防结块性、早期抗起泡性、耐擦洗性和耐水洗性、抗污性和抗划伤性。
发明内容
本发明通过在第一方面提供一种化合物解决了现有技术中的需求,所述化合物是式I化合物的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物:
其中m为1到60。
在第二方面,本发明是一种方法,其包含在足以产生麦芽糊精的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物的条件下,在路易斯酸催化剂的存在下,将麦芽糊精与二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚接触的步骤,其中所述麦芽糊精由式I表示:
其中m为1到60,并且所述二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚由式II表示:
其中每个R独立地为F、Cl、Br、CN、C1-C6烷基或C1-C6烷氧基;R1为H或1-苯乙基;以及每个n独立地为0、1、2或3。
本发明的化合物可用作涂料调配物中的开放时间添加剂。
具体实施方式
本发明是一种化合物,所述化合物是式I化合物的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物:
其中m为1到60。
可通过在反应条件下将环氧卤丙烷与式IIa的二苯乙烯基和/或三苯乙烯基一元酚接触制备所述二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚:
其中R、R1和n如前所限定,以形成式II的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚。
优选通过在碱存在下将环氧卤丙烷与式IIa化合物接触制备式II化合物,所述碱为诸如碱金属或碱土金属氢氧化物、碳酸盐或碳酸氢盐或它们的混合物。合适的碱的实例包括NaOH、KOH、Na2CO3、K2CO3、NaHCO3、KHCO3、NaH和KH,其中优选的为NaOH水溶液。优选的环氧卤丙烷为环氧氯丙烷。在另一种环氧化方法中,式II化合物可与碱金属氢化物(如NaH或KH)反应,随后与环氧卤丙烷反应。
可在合适溶剂的存在下进行所述方法,所述合适溶剂为诸如甲苯、甲基异丁基酮、二氯甲烷或异丙醇。或者,可没有任何辅助溶剂进行所述反应,其中环氧卤丙烷起到试剂和溶剂二者的作用。在任何情况下,环氧卤丙烷有利地以相对于式IIa化合物化学计量过量地使用。
通常在大气压力下或约大气压力下,在优选地从25℃到70℃范围内的温度下,将所述方法进行一段时间,以实现转换成所需产物。
可通过本领域公知的各种方法进行所需产物的回收和纯化;其中环氧氯丙烷被用作溶剂,将真空蒸馏法有利地用于去除和再循环。
在路易斯酸存在下,式II化合物(优选其中每个n都为0)与式I化合物接触以形成式I化合物的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物。路易斯酸的实例包括BF3、ZnCl2、MgBr2、SnCl4、TiCl4、FeCl3、AlCl3、MeAlCl2、Me2AlCl和LiClO4,其中优选BF3。优选在极性非质子性溶剂(诸如二甲基乙酰胺)的存在下,优选在以下范围内的温度下进行所述反应:从25℃、更优选从40℃,最优选至60℃、至165℃、更优选至125℃、最优选至100℃。优选地,在基本上无水、更优选在无水的条件下进行所述反应。
如本文所用,术语“式I化合物的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物”是指自式I化合物(麦芽糊精)和式II化合物的反应形成的化合物或化合物的混合物。所述加合物可以是单官能的或多官能的,优选是单官能的或双官能的,更优选是单官能的。自1摩尔式I化合物和1摩尔式II化合物(其中n为0并且R1为1-苯乙基)反应形成的单官能加合物的一个实例由下面的式III表示:
开环的缩水甘油醚基团的实际连接点可以是麦芽糊精的任何可用OH位。此外,开环的缩水甘油醚基团是由下面的异构体中的一者或二者表示的三苯乙烯基苯氧基丙醇基团:
其中虚线代表三苯乙烯基苯氧基丙醇基团的连接点至麦芽糊精分子的可用氧原子。所述加合物可以通过由基质辅助激光解吸电离质谱法(MALDI-MS)测量的数均分子分子量(Mn)表征。通过定义,假定的是,在质谱中观察到的所有强度的响应因子都相同。加合物的Mn范围为800至10000道尔顿。
不受理论束缚,可以认为庞大的疏水性二苯乙烯基和/或三苯乙烯基对乳胶粒子表面有很强的亲和力,并且在胶体周围形成保护层,同时亲水部分在粒子之间产生空间位阻排斥。这些特征导致了乳胶粒子聚结的延迟,从而增加了开放时间。
实例
中间体实例1-制备三苯乙烯基苯酚单缩水甘油醚
在2升3颈圆底反应器中装入三苯乙烯基苯酚(式II化合物(其中m=0),200.0克,获自Saltigo GmbH,Leverkusen,DE,66%1,3,5-三苯乙烯基苯酚,26%2,6-二苯乙烯基苯酚)和环氧氯丙烷(455.4克)。然后搅拌加入异丙醇(245.2克),接着加入去离子(DI)水(39.6克)。将反应器的内容物加热到51℃,此时经20分钟逐滴加入NaOH水溶液(17.7克,于70.9克去离子水中)。将混合物加热并再搅拌20分钟,此后将内容物沉淀4分钟,形成双相混合物。将水层从反应器中去除,留下清澈的有机材料。将内容物加热到50℃,同时搅拌4分钟,在此时,经15分钟逐滴加入第二份NaOH水溶液(7.9克,于31.5克水中)。将反应物搅拌并再加热20分钟,此后沉淀反应器内容物,形成双相混合物。去除水层,留下清澈的淡黄色有机层。
再次将内容物加热到50℃,同时搅拌1分钟,此后经4分钟逐滴加入第三份NaOH水溶液(2.0克,于7.9克去离子水中)。将反应物搅拌并再加热16分钟,此后将反应器的内容物转移至分液漏斗,并沉淀。去除水层,并用去离子水洗涤有机部分三次。对于第三次清洗,将双相混合物沉淀45分钟。在支撑于侧臂烧瓶上烧结玻璃漏斗中的Na2SO4上干燥所得的有机层,然后真空过滤。在真空中去除溶剂,得到透明的淡黄色粘稠液体(215.19克),如环氧化物滴定法和气相色谱分析所证实,发现所述粘稠液体为三苯乙烯基苯酚的单缩水甘油醚和二苯乙烯基苯酚的单缩水甘油醚的混合物。
实例1-麦芽糊精的三苯乙烯基苯酚单缩水甘油醚加合物的制备
将葡萄糖当量为16.5至19.5的来自Sigma-Aldrich的麦芽糊精(10克,约0.01摩尔)溶解于无水二甲基乙酰胺(50毫升)中。将溶液用导管移入预干燥的装有磁力搅拌棒的250毫升反应烧瓶中。将一份实例1的二苯乙烯基和三苯乙烯基苯酚单缩水甘油醚(TSP-GE,4.62克,0.01摩尔)引入到用N2吹扫的预干燥的50毫升单颈圆底烧瓶中;然后,将15毫升无水二甲基乙酰胺用导管移入反应烧瓶中。TSP-GE经30分钟的时间溶解,然后用导管移入含有麦芽糊精的反应烧瓶中。然后将BF3乙醚络合物(1毫升)加入到烧瓶中,此时将反应内容物加热到80℃后维持21小时。约15小时反应时间后,将额外的BF3乙醚络合物(1毫升)加入到反应烧瓶中。在21小时的加热周期完成之后,将反应的内容物在室温下再搅拌24小时。将NaOH(5毫升的0.05摩尔NaOH,接着是1.5毫升的50%NaOH)添加到内容物中,接着添加乙酸(1毫升)。在真空中去除二甲基乙酰胺,接着对样品进行冷冻干燥。得到灰白色粉末。经1HNMR(δ7.47-6.87,17H,δ5.25-3.01,60H,δ2.39-1.69,15H,δ1.66-1.31,8H)和MALDI-TOF质谱(每组峰分开162Da,且作为一组峰的实例:m/z=1937.7、1961.6、1985.5Da,其中Z是每摩尔的装填量)确认结构。在1961.6处的峰与单取代的麦芽糊精的存在相符(m=8);在1985.5处的峰与未取代的麦芽糊精的存在相符(m=11);并且在1937.7处的峰与双取代的麦芽糊精的存在相符(m=5)。
MALDI-TOF测量
在装备有氮激光器(λ=337纳米)的Bruker Daltonics ultraflex MALDI-TOF质谱仪上获得MALDI质谱。在MALDI实验中,将20毫克的2,5-二羟基苯甲酸溶于1毫升的THF中。以5毫克/毫升的浓度将实例1溶解在二甲基乙酰胺中。以1:10v/v的比例将溶液与基质溶液预混合。将NaI加入到样品/基质混合物中,且然后将0.3微升的混合物放在样品板上且经空气干燥以用于MALDI-MS分析。
制备具有麦芽糊精的缩水甘油醚加合物的涂料调配物:
在以下筛选调配物中评估实例1的麦芽糊精的缩水甘油醚加合物的开放时间:
表1-具有开放时间添加剂的涂料调配物
根据ASTM-D7488测量开放时间。发现具有实例1添加剂的调配物的开放时间为7分钟,而没有任何添加剂的调配物的开放时间为5至6分钟。
Claims (9)
1.一种化合物,其为式I化合物的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物:
其中m为1到60。
2.根据权利要求1所述的化合物,其中所述式I化合物的加合物为单官能或双官能加合物。
3.根据权利要求1所述的化合物,其中所述式I化合物的加合物为三苯乙烯基苯酚单缩水甘油醚的单官能加合物。
4.根据权利要求1所述的化合物,其数均分子量为800到10,000道尔顿。
5.根据权利要求4所述的化合物,其经一个或两个二苯乙烯基苯氧基丙醇基团或一个或两个三苯乙烯基苯氧基丙醇基团;或一个二苯乙烯基苯氧基丙醇基团和一个三苯乙烯基苯氧基丙醇基团取代。
6.根据权利要求4所述的化合物,其经一个三苯乙烯基苯氧基丙醇基团取代。
7.一种方法,其包含在足以产生麦芽糊精的二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚加合物的条件下,在路易斯酸的存在下,将所述麦芽糊精与二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚接触的步骤,其中所述麦芽糊精由式I表示:
其中m为1到60,并且所述二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚由式II表示:
其中每个R独立地为F、Cl、Br、CN、C1-C6烷基或C1-C6烷氧基;R1为H或1-苯乙基;且每个n独立地为0、1、2或3。
8.根据权利要求7所述的方法,其中所述麦芽糊精与所述二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚在无水条件下,在极性非质子性溶剂中,在60℃到125℃范围内的温度下接触在一起,其中所述路易斯酸为三氟化硼,并且其中n为0。
9.根据权利要求8所述的方法,其中所述麦芽糊精与所述二苯乙烯基和/或三苯乙烯基苯酚单缩水甘油醚在60℃到100℃范围内的温度下接触在一起。
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Families Citing this family (4)
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CA2948961C (en) | 2015-12-28 | 2023-12-05 | Dow Global Technologies Llc | Polyether-urethane-urea additives for block resistance and open time |
BR112018075197B1 (pt) | 2016-07-05 | 2022-07-12 | Dow Global Technologies Llc | Composição, e, tinta látex |
AU2018203941B2 (en) * | 2017-06-27 | 2024-04-18 | Dow Global Technologies Llc | Glycidyl ether alkoxylate block copolymers |
WO2019074896A1 (en) | 2017-10-10 | 2019-04-18 | Stepan Company | POLYMER DISPERSANTS OBTAINED FROM ARALKYL PHENOLS |
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Also Published As
Publication number | Publication date |
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CN106892985B (zh) | 2020-11-13 |
US10604590B2 (en) | 2020-03-31 |
BR102016028437A2 (pt) | 2017-06-20 |
EP3181590B1 (en) | 2019-01-30 |
EP3181590A1 (en) | 2017-06-21 |
MX2016015515A (es) | 2017-06-16 |
US20170174793A1 (en) | 2017-06-22 |
CA2948965A1 (en) | 2017-06-17 |
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