CN114599748B - 用于易洁涂层的水基性uv可固化涂料组合物 - Google Patents
用于易洁涂层的水基性uv可固化涂料组合物 Download PDFInfo
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- CN114599748B CN114599748B CN202080070963.2A CN202080070963A CN114599748B CN 114599748 B CN114599748 B CN 114599748B CN 202080070963 A CN202080070963 A CN 202080070963A CN 114599748 B CN114599748 B CN 114599748B
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Abstract
本发明涉及合成含有全氟聚醚嵌段的羧基官能性不饱和聚氨基甲酸酯,其可用作制备水基性UV可固化涂料组合物的易洁添加剂。该聚氨基甲酸酯可通过包括以下步骤的方法制备:a)使羟基封端的全氟聚醚A与摩尔过量的聚异氰酸酯B进行反应以获得异氰酸酯官能性氨基甲酸酯C,b)将羧基官能性多元醇D添加至反应混合物中,c)将OH‑官能性(甲基)丙烯酸酯单体E添加至该反应混合物中,其中步骤(b)及步骤(c)可按任何次序进行,及d)用中和剂F中和该反应产物。所得涂层具有容易清洁及防污特性。
Description
技术领域
本发明涉及羧基官能性不饱和聚氨基甲酸酯的合成及含有其的水基性UV可固化涂料组合物。涂料组合物可用于制造易洁涂层,其尤其适用于消费型电子装置或汽车涂层的领域。
先前技术
在消费型电子装置(如蜂巢式电话、平板计算机、膝上型计算机及汽车内饰)的领域中,使用各种基材,如塑料、金属及玻璃。通常需要用容易清洁及防污涂层覆盖这些基材。容易清洁意谓表面防水、油和/或污垢。易洁涂层减少或消除清洁表面的需要。
此项技术中已知氟化聚合物,特别是全氟聚醚(PFPE),具有不粘及润滑特性且可用于产生易洁涂层。然而,该树脂仅可溶于氟化溶剂,且因此难以在不使用特殊溶剂的情况下用于涂料配制物中。当有人希望在水基性涂料组合物中使用该树脂时,该问题甚至更大,因为氟化树脂通常不会充分分散于水中。因此,容易清洁特性的改进通常伴随水分散性的恶化。因此,大部分易洁涂层通常为溶剂性的。
需要提供易洁涂料组合物,优选为水基性涂料组合物。也需要涂层为耐用、防污且可耐受磨损。进一步需要涂层充分粘附于用于消费型电子装置或汽车工业中的基材,尤其粘附于塑料基材。
发明内容
为了解决以上提及的需求,本发明在第一方面中提供一种含有全氟聚醚嵌段的羧基官能性不饱和聚氨基甲酸酯,通过凝胶渗透层析法利用聚苯乙烯标准物及四氢呋喃作为移动相测定,该聚氨基甲酸酯的分子量Mn在1,000至5,000范围内,该聚氨基甲酸酯通过包括以下步骤的方法制备:
a)使羟基封端的全氟聚醚A与摩尔过量的聚异氰酸酯B进行反应以获得异氰酸酯官能性氨基甲酸酯,
b)使异氰酸酯官能性氨基甲酸酯与羧基官能性多元醇D进行反应,
c)使异氰酸酯官能性氨基甲酸酯与单-OH-官能性(甲基)丙烯酸酯单体E进行反应,
d)用中和剂G中和步骤b)或c)的反应产物,
其中步骤(b)及(c)可按任何次序进行且其中该方法不包括用二胺或二醇进行的扩链。
在另一方面中,本发明提供一种水基性UV可固化涂料组合物,其包含根据本发明的聚氨基甲酸酯的水性分散体及不同于聚氨基甲酸酯的至少一种聚合物,其中以涂料组合物的树脂固体计,聚氨基甲酸酯以0.01-20重量%的量存在。
本发明还提供一种涂覆基材的方法,该方法包括将根据本发明的涂料组合物涂覆至基材且通过UV辐射固化涂料组合物。
在又一方面中,本发明提供一种根据本发明获得的经涂覆的基材。
附图简单说明
图1展示涂覆有具有永久性标记线的(a)比较涂层(涂层1(Coating 1))及(b)根据本发明的涂层(涂层2(Coating 2))的基材。
图2展示在容易清洁测试之后,涂覆有(a)比较涂层(涂层1)及(b)根据本发明的涂层(涂层2)的基材。
图3(a)展示在用永久性标记绘制之后根据本发明的涂层3的防油墨能力。图3(b)展示已用纸巾将油墨擦掉之后的基材。
实施方式
本发明中所使用的聚合物为基于全氟聚醚(PFPE)树脂的羧基官能性不饱和聚氨基甲酸酯。其可通过包括以下步骤的方法制备。
步骤(a)
在第一步骤(a)中,使羟基封端的全氟聚醚A与摩尔过量的聚异氰酸酯B进行反应以获得异氰酸酯官能性氨基甲酸酯C。
(全)氟聚醚(PFPE)为氟化聚合物,其包含直链或支化的完全或部分氟化的聚环氧烷链,该聚环氧烷链含有具有至少一个悬链线醚键及至少一个氟碳化物部分的重现单元。PFPE可分成非官能性及官能性的;前者包含末端带有(全)卤代烷基的PFPE链,而后者包含具有至少两个末端的PFPE链,其中至少一个末端包含官能团。官能性PFPE,尤其单官能性及双官能性PFPE,包含具有两个末端的PFPE链,其中一个或两个末端带有官能团。优选使用双官能性PFPE。PFPE优选不含有有机硅基团,例如聚硅氧烷链。尽管已知聚硅氧烷链用于具有容易清洁效能的涂层,但认为其在油及水接触角方面比PFPE具有更差效能。羟基封端的全氟聚醚为在两端中的每一处含有一个或多个OH基团的官能性全氟聚醚(PFPE)。羟基封端的全氟聚醚A的数目平均分子量优选为400至3000。Mn可通过凝胶渗透层析法(GPC)使用聚苯乙烯标准物与四氢呋喃作为移动相来测定。
羟基封端的全氟聚醚A可具有通式结构HO-(CF2-CF2-O)n-OH或HO-(CF2-CF2-O)n-(CF2-O)m-OH。其也可包括具有环氧乙烷单元的嵌段且具有以下通式结构:
HO-(CH2CH2O)p-CH2-CF2-Rf-CF2-CH2-(OCH2CH2)q-OH
其中p和q为独立地选自0至50、优选1至50的整数,其中Rf表示具有全氟聚醚结构(CF2CF2O)n、(CF2O)m或(CF2-CF2-O)n-(CF2-O)m的双官能团,其中n及m为独立地选自1至100的整数。当p和q均不为零时,所得聚合物在水中具有优选分散性。优选地,p在1-5范围内且q在1-5范围内。
羟基封端的全氟聚醚可以PFPE或/>PFPE,例如5174X、/>E10H、/>PEG45购自Solvay。
聚异氰酸酯B为具有反应性异氰酸酯基的化合物且具有至少2的官能度。也可使用聚异氰酸酯的混合物。聚异氰酸酯可为脂族或芳族的。适合的聚异氰酸酯的实例包括六亚甲基二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯和/或2,4,4-三甲基六亚甲基二异氰酸酯、对四甲基二甲苯二异氰酸酯及间四甲基二甲苯二异氰酸酯、亚甲基双(异氰酸4-环己酯)(氢化MDI)、异氰酸4,4-亚甲基二苯酯(MDI)、对亚苯基二异氰酸酯及间亚苯基二异氰酸酯、2,4-甲苯二异氰酸酯和/或2,6-甲苯二异氰酸酯(TDI)及其添加物,以及异佛尔酮二异氰酸酯(IPDI)。优选聚异氰酸酯包括脂族二异氰酸酯,如IPDI、MDI及六亚甲基二异氰酸酯。
反应在摩尔过量的异氰酸酯中进行。A与B的官能团的摩尔比优选为1:1.1至1:5,更优选为1:2至1:4。在反应期间,需要使PFPE的所有官能团反应且在其他步骤中保留一定量的聚异氰酸酯B用于反应。异氰酸酯过量也使分子量保持相对较低,因为其防止在同一链中形成具有若干PFPE片段的聚合物链。优选地,异氰酸酯官能性氨基甲酸酯C在聚合物链中不具有超过一个PFPE片段。
形成氨基甲酸酯化合物的反应条件一般为本领域熟练技术人员所已知。反应温度可在40-160℃范围内,优选在50-100℃范围内。可使用已知催化剂,如二月桂酸二丁基锡(DBTDL)、辛酸亚锡、重氮双环(2.2.2)辛烷(DABCO)、Zn ACAC、辛酸锡。催化剂的量优选为每100重量份氨基甲酸酯成型单体0.005至1重量份。可利用适合的溶剂,如乙酸正丁酯、N-甲基-吡咯烷酮、甲苯及其类似物。优选地,溶剂为可与水混溶的。
步骤(a)中获得的包含全氟聚醚嵌段的异氰酸酯官能性氨基甲酸酯C按任何次序进行以下两个步骤(b)及(c)。重要的是,进行步骤(b)及(c)两者。
步骤(b)
在步骤b)中,在氨基甲酸酯形成条件下将羧基官能性多元醇D添加至反应混合物中。
优选地,羧基官能性多元醇D为二醇,更优选为聚酯二醇。优选地,其含有至少一个羧酸基。优选地,羧基为第三酸基。
优选地,化合物D具有下式:
其中R为氢或C1-16烷基。优选地,R为C1-C3烷基。更优选地,化合物D为2,2-二羟甲基丙酸(DMPA)或2,2-二羟甲基丁酸(DMBA)。该化合物为可商购的,例如来自GEO Chemicals的DMPA HA-0135。
化合物D也可为聚合物,例如酸官能性线性聚酯多元醇。该化合物为可商购的,例如来自GEO Chemicals的DMPA多元醇HA-0135LV2。
若化合物D为聚合物,则其OH值优选为20-190,更优选为50-150mg KOH/g树脂。其酸值优选为20-250、更优选50-200mg KOH/g树脂。酸值可通过电位滴定来测量,例如根据DIN EN ISO 3682。羟基值可通过电位滴定使用TSI方法来测量,例如根据ASTM E1899-08。
与羧基官能性多元醇D的反应允许将羧基引入聚合物链中,促成所得聚合物的水分散性。
在一些实施方案中,步骤b)在步骤c)之前进行。在这些实施方案中,不需要监测NCO含量。优选地,步骤b)的反应在过量异氰酸酯基(例如存在聚异氰酸酯B)的条件下进行,以便获得可与步骤c)中的OH-官能性(甲基)丙烯酸酯单体E反应的异氰酸酯官能性聚合物。异氰酸酯官能性氨基甲酸酯与羧基官能性多元醇D的官能团的摩尔比优选为1:1.1至1:5,更优选为1:2至1:4。
在其他实施方案中,步骤b)在步骤c)之后进行。在这些实施方案中,通过随时间分析NCO含量来监测反应进程。当不再侦测到NCO含量时,反应停止。
氨基甲酸酯反应的反应条件为本领域熟练技术人员所已知。通常,可使用针对步骤(a)所描述的条件。
步骤(c)
在步骤c)中,在氨基甲酸酯形成反应的条件下将OH-官能性(甲基)丙烯酸酯单体E添加至反应混合物中。
OH-官能性(甲基)丙烯酸酯单体E具有至少一个OH基团且其优选具有1至5个(甲基)丙烯酸酯基。更优选地,其仅具有一个羟基(单官能性醇)。优选使用分子质量不高于1,500的化合物。适合的化合物包括多元醇的(甲基)丙烯酸酯,例如乙二醇、新戊四醇及二新戊四醇的(甲基)丙烯酸酯。实例包括(甲基)丙烯酸2-羟乙酯、新戊四醇(甲基)丙烯酸酯、新戊四醇二(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、二新戊四醇(甲基)丙烯酸酯、二新戊四醇二(甲基)丙烯酸酯、二新戊四醇三(甲基)丙烯酸酯、二新戊四醇四(甲基)丙烯酸酯及二新戊四醇五(甲基)丙烯酸酯。优选化合物E为二新戊四醇五丙烯酸酯(DPPA)。
氨基甲酸酯反应的反应条件为本领域熟练技术人员所已知。通常,可使用针对步骤(a)所描述的条件。
在一些实施方案中,步骤c)在步骤b)之后进行。在这些实施方案中,通过随时间分析NCO含量来监测反应进程。当不再侦测到NCO含量时,反应停止。
在其他实施方案中,步骤c)在步骤b)之前进行。在这些实施方案中,不需要监测NCO含量。优选地,步骤c)的反应在过量异氰酸酯基的条件下进行,以便获得可与步骤b)中的羧基官能性多元醇D反应的异氰酸酯官能性聚合物。可能需要在步骤b)之前进行步骤c),即在添加多元醇D之前添加单体E,以便防止由成型单体E及多元醇D的多个重复片段所引起的扩链。
可使用已知催化剂,如先前所提及的。优选地使用二月桂酸二丁基锡(DBTDL)。催化剂的量优选为每100重量份氨基甲酸酯成型单体0.005至1重量份。也可使用已知抑制剂,如丁基化羟基甲苯(butylated hydroxytoluene;BHT)。
在进行步骤(b)及步骤(c)两者(按任何次序)之后,获得羧基官能性不饱和聚氨基甲酸酯。通过结构,可认为是具有氨基甲酸酯片段的PFPE链的改质,以引入官能团以便实现水分散性及UV固化。
重要的是,此聚氨基甲酸酯具有足够低的分子量。在不希望受理论束缚的情况下,认为低分子量使得有可能将此聚氨基甲酸酯作为易洁添加剂与不同(非氟化)主基料树脂组合用于涂层中。在涂层固化时,低重量添加剂可迁移至表面且履行其容易清洁特性。对于最优选迁移特性及相关容易清洁特性,聚氨基甲酸酯的重量平均分子量Mw优选在2,000-20,000范围内,更优选在4,000-15,000范围内。Mw的最优选范围包括2,000-12,000及4,000-9,000。聚氨基甲酸酯的数目平均分子量Mn优选在1,000-5,000范围内,更优选在1,000-3,000范围内。分子量Mn及Mw可通过凝胶渗透层析法(GPC)利用聚苯乙烯标准物及四氢呋喃作为移动相来测定。
所得聚氨基甲酸酯的酸值优选在10-50mg KOH/g范围内。酸值可通过电位滴定来测量,例如根据DIN EN ISO 3682。优选地,所得聚氨基甲酸酯不具有OH官能团。羟基值优选<5mg KOH/g,更优选为0mg KOH/g。羟基值可通过电位滴定使用TSI方法来测量,例如根据ASTM E1899-08。
步骤(d)
在步骤(d)中,用中和剂F中和羧基官能性不饱和聚氨基甲酸酯。中和剂F可为氨或叔胺或胺的混合物。
中和剂F优选为饱和叔胺,例如三乙胺、三丙胺、三乙醇胺、二亚乙基三胺、甲胺及N,N-二甲基乙醇胺(DMEA)。优选地,使用DMEA。使用饱和叔胺(如DMEA)的优点为所得聚合物优选可分散于水中。
中和剂F也可为烯属不饱和叔胺,特别是具有(甲基)丙烯酸酯官能团的叔胺。这些的实例包括丙烯酸2-(二乙基氨基)乙酯、甲基丙烯酸2-(二乙基氨基)乙酯、丙烯酸2-(二甲氨基)乙酯、甲基丙烯酸2-(二甲氨基)乙酯、丙烯酸叔丁基氨基乙酯、甲基丙烯酸叔丁基氨基乙酯。优选地,中和剂F包含2-(二甲氨基)-乙基-甲基丙烯酸酯或2-(二甲氨基)-乙基-丙烯酸酯。不饱和胺可促成涂料组合物的较高交联密度,由此改进涂料的物理特性。
中和剂F优选以实现聚氨基甲酸酯的羧酸基的20-150%、更优选80-120%的中和程度的量添加,中和程度计算为来自中和剂的碱基与来自聚氨基甲酸酯的羧酸基的摩尔比。
所得经中和的聚氨基甲酸酯可分散于水中。或者,其可以有机溶剂中的溶液形式提供,随后分散。在后一种情况下,优选使用与水可溶或可与水混溶的有机溶剂。该溶剂的实例包括丙酮、乙酸甲氧基丙酯(PMA)、乙酸丁酯等。当制备水基性涂料组合物时,可与水混溶的溶剂的存在使得在水中乳化更容易。
为了保持分子量较低,需要该方法不含有扩链步骤,例如在聚氨基甲酸酯制备中常见的二胺或二醇。通常,此类步骤将在分散于水中之后进行(步骤(d))。
所获得的聚氨基甲酸酯溶液的固体含量优选在30-70重量%范围内。
所获得的聚氨基甲酸酯可用作制备涂料组合物的易洁添加剂。优选地,聚氨基甲酸酯的溶液按原样使用且进一步乳化(分散于水中)。如果需要,在合成期间使用的溶剂可通过已知方法,例如通过蒸馏自分散体移除。
涂料组合物
在另一方面中,本发明提供一种水基性UV可固化涂料组合物,其包含上述羧基官能性不饱和聚氨基甲酸酯作为添加剂。聚氨基甲酸酯与涂料组合物中的其他聚合物组合使用。使用聚氨基甲酸酯作为添加剂而非作为主要树脂的优点包括例如成本低。良好易洁效能可已通过较低量的添加剂与已知基料树脂组合来实现。
以涂料组合物的总树脂固体重量计,本发明的不饱和聚氨基甲酸酯优选地以0.01-20重量%、或0.05-15重量%、或0.1-5重量%的量使用。总树脂固体重量包括所有基料树脂及交联剂(若存在)的重量,但不包括颜料及添加剂(若存在)的重量。
涂料组合物进一步包含与上文所描述的聚氨基甲酸酯不同的至少一种聚合物。优选地,聚合物为非氟化的。该聚合物可为例如聚酯、聚氨基甲酸酯、(甲基)丙烯酸酯。优选地,另一聚合物也可为辐射可固化的,优选UV可固化的。聚合物可为聚(甲基)丙烯酸酯或其混合物。在“聚(甲基)丙烯酸酯”下,应理解,聚合物具有可交联(甲基)丙烯酸酯官能团。实例包括聚(甲基丙烯酸甲酯)、聚(甲基丙烯酸)、聚甲基丙烯酸酯、聚(甲基丙烯酸乙酯)、聚(甲基丙烯酸2-羟乙酯),且也包括聚氨基甲酸酯(甲基)丙烯酸酯或聚酯(甲基)丙烯酸酯。至少一种其他聚合物的含量优选为涂料组合物的总固体含量的10至90重量%。优选地,以涂料组合物的总重量计,涂料组合物包含30至80重量%的量的至少一种聚(甲基)丙烯酸酯或聚(甲基)丙烯酸酯的混合物。
涂料组合物也可包含可共聚单体及低聚物作为反应性稀释剂。该单体的实例包括(甲基)丙烯酸酯单体,特别是(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸乙酯己酯、二新戊四醇六丙烯酸酯、丙烯腈、甲基丙烯酰胺。也可使用乙烯基单体,例如乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、苯乙烯。
优选地,涂料组合物包含至少一种光引发剂或其混合物。当曝露于辐射能时,光引发剂产生自由基。可使用此项技术中已知的任何适合的UV光引发剂。适合的光引发剂包括安息香衍生物、苯偶酰缩酮、α-羟烷基苯酮、单酰基氧化膦(MAPO)及双酰基氧化膦(BAPO),如二苯基(2,4,6-三甲基苯甲酰基)氧化膦、1-羟基-环己基-苯基-酮、双(2,4,6-三甲基苯甲酰基)-苯基氧化膦、双(2,6-二甲氧基苯甲酰基)-2,4,4-三甲基戊基-氧化膦、2-羟基-2-甲基-1-苯基-丙-1-酮、2-甲基-1[4-(甲硫基)苯基]-2-吗啉酮-丙-1-酮、苯基乙醛酸甲酯。也可采用这些化合物的混合物。光引发剂为可商购的,例如来自IGM Resins。
以组合物的总重量计,光引发剂优选以0.1至10重量%、例如0.5至5.0重量%、或0.5至2.5重量%的量存在。
涂料组合物优选为水基性的。当制备和/或涂覆涂料组合物时,水基性涂料组合物包含水作为主要液相。“主要液相”意谓水占液相的至少50重量%,优选至少80重量%,更优选至少90重量%,在一些实施方案中甚至100重量%。以涂料组合物的总重量计,涂料组合物优选含有20至80重量%的水。
任选地,涂料组合物可此外含有有机溶剂。例如,有机溶剂可以液相的至多40重量%、优选至多30重量%存在。在一些实施方案中,按涂料组合物的总重量计,涂料组合物优选含有小于10重量%的有机溶剂,或甚至不含有有机溶剂。
适合的有机溶剂的实例包括醇(如乙醇、异丙醇、正丁醇、正丙醇)、酯(如乙酸乙酯、乙酸丙酯)、芳族溶剂(如甲苯)、酮溶剂(如丙酮、甲基乙基酮、甲基异丁基酮、环己酮、二丙酮醇);脂族烃;氯化烃(如CH2Cl2);醚(如乙醚、四氢呋喃、丙二醇单甲醚)及其混合物。优选地,溶剂为可与水混溶的。优选有机溶剂包括乙酸丁酯、甲基异丁基酮(MIBK)、甲基乙基酮(MEK)、丙二醇单甲醚及乙酸甲氧基丙酯(PMA)或其混合物。
根据本发明的涂料组合物的固体含量可在1至90重量%、优选5至65重量%、更优选10至50重量%范围内。
涂料组合物可进一步包含已知添加剂,如填充剂、抗氧化剂、消光剂、颜料、耐磨粒子、流动控制剂、表面活性剂、塑化剂、粘着促进剂、触变剂、光稳定剂及其他。
本发明进一步提供一种涂覆基材的方法,该方法包括将根据本发明的涂料组合物涂覆至基材且通过UV辐射固化涂料组合物。
可通过已知技术将涂料组合物涂覆于广泛范围的基材上,该技术包括喷雾、辊压、刮涂、倾注、刷涂或浸渍。在水及任选地选用的有机溶剂(若存在)蒸发之后,涂料组合物产生脱尘干燥至略有粘性的涂层。
固化随后通过UV辐射诱导。可使用任何适合的UV辐射来源,例如Hg灯、金属卤化物灯、氙气灯、UV-LED灯。优选使用UV-LED灯。本领域熟练技术人员能够确定适合于通过UV辐射固化的条件。
可在环境条件(例如,室温)下进行涂料组合物的固化。室温在此处理解为15至30℃。也可通过加热来加速固化。经涂覆的基材可加热至40-100℃,更优选50-80℃范围内的温度。可使用已知方法,例如放置于烘箱中。加热优选在UV固化之前或同时进行。
根据本发明的涂料组合物可涂覆于包括金属及非金属基材的广泛范围的基材。适合的基材包括聚碳酸酯丙烯腈丁二烯苯乙烯(PC/ABS)、聚碳酸酯、聚丙烯酸酯、聚烯烃、聚酰胺、聚苯乙烯、聚酰胺、玻璃、木材、石材、铝、铝合金及其类似物。
根据本发明的涂料组合物可用作直接涂覆至基材的单层,或在多层系统中,例如用作底漆、底涂层或透明涂层。
根据本发明的涂料组合物可用于各种涂料工业中,如消费型电子装置、汽车、封装、木地板及家具、家用电器、玻璃及窗、体育设备。
本发明进一步提供涂覆有自本发明的涂料组合物获得的涂层的基材。根据本发明的涂层具有包括粘着力及耐磨性的格外良好的一般特性。此外,如可通过永久性标记笔测试,涂层也具有极佳的容易清洁及防污特性。
实施例
将参考以下实施例证明本发明。除非此外规定,否则所有份数及百分比均以重量计。
氟连接E10H-来自Solvay、Mn约1600的羟基官能性PFPE聚合物
DPPA-来自Kayaku chemical(Wuxi)有限公司的二新戊四醇五丙烯酸酯.
DMBA-来自Shanghai Dibo Biotechnology有限公司的二羟甲基丁酸.
HA-0135LV2-DMPA多元醇,来自GEO Specialty Chemicals的酸官能性线性聚酯多元醇,酸值为100-115mg KOH/g,OH值为100-115mg KOH/g
DMEA-二甲基乙醇胺
实施例1.聚氨基甲酸酯1的合成
将异佛尔酮二异氰酸酯(15.42g)、乙酸正丁酯(17.6g)、二月桂酸二丁基锡(0.1g)及丁基化羟基甲苯(0.1g)放置于安装有有搅拌器及冷凝器的四颈圆底烧瓶中。在60℃下将氟连接E10H(58.97g)滴加至混合物中持续一小时。在60℃下加热反应混合物持续半小时。随后将DPPA(20.47g)在80℃下在半小时内滴加至混合物中且将混合物在80℃下蒸煮持续半小时。随后在80℃下将二羟甲基丁酸(DMBA)(5.14g)添加至混合物中,在80℃下蒸煮持续一小时。随后使温度升高至90℃,且进行反应直至无法侦测到NCO基团。将反应混合物冷却至60℃且将DMEA(3.41g)添加至混合物中且在60℃下再搅拌半小时。
所得聚氨基甲酸酯具有Mn 1106、Mw 4948、PD 4.5。中和之前聚氨基甲酸酯的酸值为19.5mg KOH/g,OH值为0mg KOH/g。
实施例2.聚氨基甲酸酯2的合成
将异佛尔酮二异氰酸酯(20.05g)、乙酸正丁酯(25g)、二月桂酸二丁基锡(0.1g)及丁基化羟基甲苯(0.1g)放置于安装有有搅拌器及冷凝器的四颈圆底烧瓶中。在60℃下将氟连接E10H(38.34g)滴加至混合物中持续一小时。在60℃下加热反应混合物持续半小时。随后在60℃下在半小时内将HA-0135LV2(14.99g)滴加至混合物中且将混合物在80℃下加热持续半小时。随后在80℃下将DPPA(26.62g)添加至混合物中且在80℃下蒸煮持续一小时。随后使温度升高至90℃,且进行反应直至无法侦测到NCO基团。随后将反应混合物冷却至60℃,添加DMEA(3.21g)且在60℃下再搅拌半小时。
所得聚氨基甲酸酯具有Mn 1497、Mw 12141、PD 8.1。中和之前聚氨基甲酸酯的酸值为27mg KOH/g,OH值为0mg KOH/g。
实施例3.涂料组合物的制备
根据下表1制备两个涂层样品。
表1.
涂层1 | 涂层2 | |
水基性UV树脂(固体含量:45%) | 60g | 60g |
聚氨基甲酸酯1的分散体(固体含量:50重量%) | 0g | 0.24g |
光引发剂(固体含量:60重量%) | 2克 | 2克 |
湿润剂 | 0.3g | 0.3g |
涂层1含有可商购的水基性UV可固化树脂(Mitsui Chemicals,Olester RA7011)。
涂层2含有与实施例1中所制备的0.4重量%聚氨基甲酸酯添加剂(于树脂固体上)相同的水基性UV可固化树脂的混合物且以50重量%于水中的分散体形式添加。
将两个配制物涂覆于PC/ABS基材上且通过曝露于紫外光来固化,形成涂层1及涂层2。
实施例4.测试
分别通过20座滴法在固化涂层的顶部上测量水接触角。液滴设定为3μl/液滴,且测量温度为约20℃。使用具有软件SCA 20的DataPhysics仪器来测量接触角。测试结果展示于下表2中。
用相同方法类似地进行油接触角测试。液滴设定为2μl/液滴,且测量温度为约20℃。测试结果也展示于下表2中。
表2.表面特性:
涂层1 | 涂层2 | |
水接触角 | 83.48 | 106.98 |
十六烷水接触角 | 22.82 | 59.85 |
根据表2,与比较涂层1相比,涂层2的水接触角及十六烷接触角通过使用根据本发明的添加剂显著增大。因此,涂层2与涂层2相比具有好得多的防污及易洁特性,其也可通过图1及图2来确认。
两个涂层的防油基墨能力及容易清洁效能
具有不同颜色的油基永久性标记笔分别用于在固化涂层的顶部上绘制线。拍摄图像以展示在两个涂层上书写的油墨的不同外观。图1展示在涂层1表面上良好扩散的油墨,图2展示红色油墨及蓝色油墨并未良好扩散,但归因于涂层2比涂层1低的表面能而收缩至涂层2表面上的珠粒。然而,黑色油墨扩散良好且不会收缩至涂层2上的珠粒,其可能归因于油墨的化学组分差异及黑色。
图1及图2展示在用干燥纸巾清洁之后涂层1及2的表面外观。油墨无法在涂层1上清洁,但所有彩色油墨可通过干燥纸巾在涂层2上完全擦掉。因此,与比较涂层1的情形相比较,涂层2中的聚氨基甲酸酯添加剂大大改进了容易清洁及防污效能。
实施例5
涂层3以与涂层2相同的方式但使用实施例2中制备的聚氨基甲酸酯2的水性50重量%分散体代替聚氨基甲酸酯1来制备。
将涂料组合物涂覆于PC/ABS基材上且通过曝露于紫外光来固化以形成涂层3。
以与实施例4相同的方式测试防油墨能力及容易清洁效能。
图3(a)展示在用永久性标记绘制之后涂层3的防油墨能力。图3(b)展示已用纸巾将油墨擦掉之后的基材。此实施例表明使用聚氨基甲酸酯2作为容易清洁添加剂的涂层的防油墨及容易清洁特性。
Claims (12)
1.一种水基性UV可固化涂料组合物,其包含聚氨基甲酸酯的水性分散体和至少一种不同于聚氨基甲酸酯的非氟化的聚合物,其中聚氨基甲酸酯作为添加剂以涂料组合物的树脂固体重量计0.1-5重量%的量存在,其中聚氨基甲酸酯为含有全氟聚醚嵌段的羧基官能性不饱和聚氨基甲酸酯,通过凝胶渗透层析法利用聚苯乙烯标准物及四氢呋喃作为移动相测定,所述聚氨基甲酸酯的分子量Mn在1,000至5,000范围内,所述聚氨基甲酸酯的水性分散体通过包括以下步骤的方法制备:
a)使羟基封端的全氟聚醚A与摩尔过量的聚异氰酸酯B进行反应以获得异氰酸酯官能性氨基甲酸酯C,
b)使异氰酸酯官能性氨基甲酸酯C与羧基官能性多元醇D进行反应,
c)使异氰酸酯官能性氨基甲酸酯C与单-OH-官能性(甲基)丙烯酸酯单体E进行反应,
其中步骤(b)及(c)可按任何次序进行,且其中在进行步骤(b)及(c)之后获得羧基官能性不饱和聚氨基甲酸酯,
d)用中和剂G中和在进行步骤(b)及(c)之后获得的羧基官能性不饱和聚氨基甲酸酯以获得中和后的聚氨基甲酸酯,
e)将中和后的聚氨基甲酸酯分散于水中,
其中所述方法不包括在将中和后的聚氨基甲酸酯分散于水中之后用二胺或二醇进行的扩链。
2.如权利要求1的涂料组合物,其中化合物A具有通式结构
HO-(CH2CH2O)p-CH2-CF2-Rf-CF2-CH2-(OCH2CH2)q-OH
其中p和q为独立地选自0至50的整数,Rf表示具有全氟聚醚结构(CF2CF2O)n、(CF2O)m或(CF2-CF2-O)n-(CF2-O)m的双官能团,其中n及m为独立地选自1至100的整数。
3.如权利要求1或2的涂料组合物,其中步骤b)在步骤c)之前进行。
4.如权利要求1或2的涂料组合物,其中步骤c)在步骤b)之前进行。
5.如权利要求1或2的涂料组合物,其中羧基官能性多元醇D为2,2-二羟甲基丙酸(DMPA)或2,2-二羟甲基丁酸(DMBA)。
6.如权利要求1或2的涂料组合物,其中单-OH-官能性(甲基)丙烯酸酯单体E为二新戊四醇五丙烯酸酯(DPPA)。
7.如权利要求1的涂料组合物,其中所述至少一种不同于聚氨基甲酸酯的非氟化的聚合物为聚(甲基)丙烯酸酯。
8.如权利要求1-7中任一项的涂料组合物,其进一步包含光引发剂。
9.如权利要求1-8中任一项的涂料组合物,其进一步包含以涂料组合物的总重量计小于10重量%的量的有机溶剂。
10.一种涂覆基材的方法,其包括将如权利要求1-9中任一项的涂料组合物涂覆至基材且通过UV辐射固化涂料组合物。
11.一种根据如权利要求10的方法获得的经涂覆的基材。
12.如权利要求11的基材,其中基材选自:聚碳酸酯丙烯腈丁二烯苯乙烯(PC/ABS)、聚碳酸酯、聚丙烯酸酯、聚烯烃、聚酰胺、聚苯乙烯、玻璃、木材、铝及铝合金。
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US20090130453A1 (en) * | 2007-10-18 | 2009-05-21 | Kazushi Tanaka | Active energy ray-curable resin composition and laminate thereof |
US20110118405A1 (en) * | 2008-04-30 | 2011-05-19 | Dic Corporation | Active-energy-ray-curable coating composition, cured product thereof, and novel curable resin |
CN103890027A (zh) * | 2011-10-17 | 2014-06-25 | 湛新比利时股份有限公司 | 氟化水-油排斥剂 |
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WO2019129692A1 (en) * | 2017-12-26 | 2019-07-04 | Akzo Nobel Coatings International B.V. | Fluorinate polyacrylate coating composition, the preparation method therefore and use thereof |
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US20090130453A1 (en) * | 2007-10-18 | 2009-05-21 | Kazushi Tanaka | Active energy ray-curable resin composition and laminate thereof |
US20110118405A1 (en) * | 2008-04-30 | 2011-05-19 | Dic Corporation | Active-energy-ray-curable coating composition, cured product thereof, and novel curable resin |
CN103890027A (zh) * | 2011-10-17 | 2014-06-25 | 湛新比利时股份有限公司 | 氟化水-油排斥剂 |
CN108300274A (zh) * | 2017-08-31 | 2018-07-20 | 浙江佑泰新材料科技有限公司 | 一种水性紫外光固化抗指纹涂料及其制备方法 |
WO2019129692A1 (en) * | 2017-12-26 | 2019-07-04 | Akzo Nobel Coatings International B.V. | Fluorinate polyacrylate coating composition, the preparation method therefore and use thereof |
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