CN102449013B - 聚氨酯分散体、生产它的方法、涂布的制品、以及涂布制品的方法 - Google Patents
聚氨酯分散体、生产它的方法、涂布的制品、以及涂布制品的方法 Download PDFInfo
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- CN102449013B CN102449013B CN2010800236230A CN201080023623A CN102449013B CN 102449013 B CN102449013 B CN 102449013B CN 2010800236230 A CN2010800236230 A CN 2010800236230A CN 201080023623 A CN201080023623 A CN 201080023623A CN 102449013 B CN102449013 B CN 102449013B
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- polyvalent alcohol
- natural oil
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Abstract
本发明是聚氨酯分散体、其制备方法、涂布制品、和涂布制品的方法。根据本发明的聚氨酯分散体包含(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括溶解在一缩二丙二醇二甲基醚中的一种或多种基于天然油的多元醇在一种或多种第一表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水。
Description
相关申请的交叉引用
本申请是非临时申请,要求2009年3月31日提交的题为“POLYURETHANE DISPERSION,METHOD OF PRODUCING THE SAME,COATED ARTICLES,AND METHOD FOR COATING ARTICLES”的美国临时专利申请61/165,013的优先权,其教导通过参考并入本申请,就像它在下文中全文再现一样。
技术领域
本发明涉及聚氨酯分散体、制备聚氨酯分散体的方法、涂布的制品、以及涂布制品的方法。
背景技术
粘合性是表面涂层应用的重要性能特性,所述表面涂层应用例如木材涂层应用、混凝土涂层应用、金属涂层应用、或塑料涂层应用。聚氨酯分散体通常由原始设备制造商或之后的个别最终用户用于这样的表面涂层应用。由于木材表面的性质和聚氨酯化学,木材表面的粘合性是受到极大挑战的。已经使用过几种不同的方法来促进木材基板上的较好的粘合性。这些方法包括,例如,在聚氨酯主链上结合硅烷官能团,结合进丙烯酸类/乙烯基官能团(例如混合物和共混物),对主链的脂肪酸改性,引入可紫外线固化的部分以及更为特殊的化学方法例如氟化、氯化。使用粘合促进剂作为添加剂促进粘合也是常见的。但是,这些方法为达到所需性能而导致成本和工作增加。
因此,需要例如在木材涂层应用、混凝土涂层应用、金属涂层应用、或塑料涂层应用中提供改善的粘合性质的聚氨酯分散体。此外,需要例如在木材涂层应用、混凝土涂层应用、金属涂层应用、或塑料涂层应用中提供改善的粘合性质的聚氨酯分散体的制备方法。
发明内容
本发明是聚氨酯分散体、制备聚氨酯分散体的方法、涂布的制品、以及涂布制品的方法。
在一种实施方式中,本发明提供聚氨酯分散体,其包含(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水。
在另一种实施方式中,本发明提供制备聚氨酯分散体的方法,包括以下步骤:(1)提供包含一种或多种预聚物的第一流,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物,并且其中所述预聚物任选地由一种或多种中和剂中和;(2)提供包含水的第二流;(3)将所述第一流和所述第二流合并在一起;(4)从而形成预聚物分散体;(5)任选地中和所述预聚物分散体;(6)使所述预聚物增链;(7)从而形成所述聚氨酯分散体。
在另一种实施方式中,本发明提供涂布的制品,其包括基板;和与所述基板的一个或多个表面相连的涂层,其中所述涂层源自包含以下物质的聚氨酯分散体:(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水。
在另一种实施方式中,本发明提供制备涂布的制品的方法,包括以下步骤:(1)选择基板;(2)选择包括聚氨酯分散体的涂层组合物,其中所述聚氨酯分散体包含以下物质(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水;(3)将所述涂层组合物施用于所述基板的一个或多个表面;(4)移除至少一部分的水;(5)从而形成所述涂布的制品。
在可替换的实施方式中,本发明提供根据前述实施方式中任一种的聚氨酯分散体、制备聚氨酯分散体的方法、涂布的制品、以及涂布制品的方法,所不同的是所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物。
附图说明
为了说明本发明,在附图中显示了示例性的形式;但是应该理解的是,本发明并不限于所示的精确排列和方式。
图1说明大豆单体(soy monomer)化学的第一实施方式;和
图2是说明剪切应力与监控早期硬度发展(early hardness development)的时间的关系图。
具体实施方式
本发明是聚氨酯分散体、制备聚氨酯分散体的方法、涂布的制品、以及涂布制品的方法。根据本发明的聚氨酯分散体包含(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种第一表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水。制备根据本发明的聚氨酯分散体的方法包括以下步骤:(1)提供包含一种或多种预聚物的第一流,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种第一表面活性剂的存在下与一种或多种异氰酸酯的反应产物,并且其中所述预聚物任选地由一种或多种中和剂中和;(2)提供包含水的第二流;(3)将所述第一流和第二流合并在一起;(4)从而形成预聚物分散体;(5)任选地中和所述预聚物分散体;(6)使所述预聚物增链;(7)从而形成所述聚氨酯分散体。
本发明的聚氨酯分散体的固体内容物的平均粒度直径为50至1000nm;例如,该平均粒度直径为50至500nm;在可替换的实施方式中,为50至500nm;在可替换的实施方式中,为50至150nm;在可替换的实施方式中,为60至100nm;在可替换的实施方式中,为60至80nm。本发明的聚氨酯分散体的固体内容物可以为20至60wt%,其中不包括任何另外的填料的重量;例如,固体内容物为30至50wt%;在可替换的实施方式中,为20至50wt%;在可替换的实施方式中,为30至40wt%。本发明的聚氨酯分散体在25℃的粘度为100至3000cPs;例如,在25℃的粘度为100至1000cPs;在可替换的实施方式中,在25℃的粘度为200至900cPs;在可替换的实施方式中,在25℃的粘度为200至600cPs。本发明的聚氨酯分散体可以包含0至30重量%、或5至25重量%、或5至20重量%、或0至20重量%的一种或多种溶剂。
根据本发明的聚氨酯分散体可以进一步包含一种或多种填料、一种或多种交联剂、一种或多种消泡剂、一种或多种颜料或着色剂、一种或多种流变学改性剂、一种或多种粘合促进剂、一种或多种耐磨和增滑剂(mar and slipagents)、一种或多种润湿剂、一种或多种防冻剂、一种或多种生物灭杀剂或抗菌剂;一种或多种表面活性剂;一种或多种UV稳定剂;一种或多种抗氧化剂;一种或多种流动控制剂、及其组合。
所述一种或多种预聚物包括溶解在一缩二丙二醇二甲基醚中的混合物在一种或多种第一表面活性剂的存在下与一种或多种异氰酸酯的反应产物,其中所述混合物包含一种或多种基于天然油的多元醇、和一种或多种己二酸酯多元醇、和任选的一种或多种短链二醇。
基于天然油的多元醇
基于天然油的多元醇是基于或源自可再生原料资源(如天然和/或基因修饰的植物的植物种籽油和/或动物源脂肪)的多元醇。这样的油和/或脂肪通常包括甘油三酯,即,与甘油相连的脂肪酸。优选的是在甘油三酯中具有至少70%不饱和脂肪酸的植物油。天然产物可以包含至少约85重量%的不饱和脂肪酸。优选的植物油的实例包括但不限于,例如,来自蓖麻、大豆、橄榄、花生、油菜籽、玉米、芝麻、棉花、芸苔(canola)、红花(safflower)、亚麻子、棕榈、葡萄籽、黑香菜(black caraway)、南瓜仁、琉璃苣籽、木菌、杏仁(apricotkernel)、阿月浑子、杏仁(almond)、澳大利亚坚果、鳄梨、海洋鼠李植物(seabuckthorn)、大麻、榛实、夜来香、野玫瑰、蓟、胡桃、向日葵、麻疯籽油(jatropha seed oils)、或其组合的那些。此外,也可以使用得自有机体如藻类的油。动物产品的实例包括猪油、牛脂、鱼油及其混合物。也可以使用基于植物和动物的油/脂肪的组合。
几种化学方法可以用来制备基于天然油的多元醇。可再生资源的这种改性包括但不限于,例如,环氧化作用、羟基化作用、臭氧分解、酯化作用、加氢甲酰化作用、或烷氧基化作用。这样的改性通常是本领域已知的。
在通过改性天然油制备这样的多元醇之后,可以对改性的产物进行进一步的烷氧基化。使用环氧乙烷(EO)或EO与其它氧化物的混合物,将亲水基团引入到多元醇中。在一种实施方式中,使改性的产物经历与足量EO的烷氧基化作用以制备包含10至60重量%EO(例如,20至约40重量%EO)的基于天然油的多元醇。
在另一种实施方式中,基于天然油的多元醇通过多步法得到,其中使动物或植物油/脂肪经受酯交换反应并回收脂肪酸组分。在该步骤之后,对脂肪酸组分中的碳-碳双键进行加氢甲酰化以形成羟基甲基基团,并然后通过羟基甲基化的脂肪酸与适当的引发剂化合物的反应形成聚酯或聚醚/聚酯。这样的多步法通常是本领域已知的,并且描述于,例如,PCT公开WO2004/096882和2004/096883。所述多步法使得产生具有疏水基团和亲水基团的多元醇,这可同时增强多元醇与水以及与常规基于石油的多元醇的溶混性。
用于制备基于天然油的多元醇的多步法的引发剂可以是用于制备常规基于石油的多元醇的任何引发剂。引发剂可以,例如,选自新戊二醇;1,2-丙二醇;三羟甲基丙烷;季戊四醇;山梨糖醇;蔗糖;甘油;二乙醇胺;烷烃二醇,如1,6-己二醇、1,4-丁二醇;1,4-环己二醇;2,5-己二醇;乙二醇;二甘醇、三甘醇;双-3-氨基丙基甲胺;乙二胺;二亚乙基三胺;9(1)-羟基甲基十八烷醇、1,4-双羟基甲基环己烷;8,8-双(羟基甲基)三环[5,2,1,02,6]癸烯;Dimerol醇(得自Henkel Corporation的36碳二醇);氢化双酚;9,9(10,10)-双羟基甲基十八烷醇;1,2,6-己三醇及其组合。在可替换的实施方式中,引发剂可以选自甘油;乙二醇;1,2-丙二醇;三羟甲基丙烷;乙二胺;季戊四醇;二亚乙基三胺;山梨糖醇;蔗糖;或任何前述的物质,其中物质中存在的醇或胺基团中的至少一个已经与环氧乙烷、环氧丙烷或其混合物发生反应;及其组合。在另一种可替换的实施方式中,引发剂是甘油、三羟甲基丙烷、季戊四醇、蔗糖、山梨糖醇、和/或其组合。
在一种实施方式中,用环氧乙烷或环氧乙烷与至少一种其它环氧烷烃的混合物将引发剂烷氧基化以得到分子量为约200至约6000(优选为约500至约3000)的烷氧基化的引发剂。
至少一种基于天然油的多元醇的官能度高于约1.5并且通常不高于约6。在一种实施方式中,该官能度低于约4。在一种实施方式中,该官能度为1.5至3。至少一种基于天然油的多元醇的羟值低于约150mg KOH/g,优选为约50至约120mg KOH/g,更优选为约60至约120mg KOH/g。在一种实施方式中,该羟值低于约100mg KOH/g。
可再生原料在基于天然油的多元醇中的含量可以为约10至约100%,通常为约10至约90%。
基于天然油的多元醇可以占多元醇共混物的至多约90重量%。但是,在一种实施方式中,基于天然油的多元醇可以占多元醇共混物总重量的至少5重量%、至少10重量%、至少25重量%、至少35重量%、至少40重量%、至少50重量%、或至少55重量%。基于天然油的多元醇可以占混合多元醇总重量的40重量%或更多、50重量%或更多、60重量%或更多、75重量%或更多、85重量%或更多、90重量%或更多、或95重量%或更多。也可以使用两种或更多种类型的基于天然油的多元醇的组合。
基于天然油的多元醇的在25℃测得的粘度通常小于约6,000mPa.s;例如,基于天然油的多元醇的在25℃测得的粘度小于约5,000mPa.s。基于天然油的多元醇的分子量可500至3000道尔顿;例如,为800至1500道尔顿。
NOP可以为与任何的下列物质的共混物:
包括基于己内酯的聚酯多元醇的脂族和芳族聚酯多元醇,任何聚酯/聚醚混合多元醇,基于PTMEG的聚醚多元醇;基于环氧乙烷、环氧丙烷、环氧丁烷及其混合物的聚醚多元醇;聚碳酸酯多元醇;聚缩醛多元醇,聚丙烯酸酯多元醇;聚酯酰胺多元醇;聚硫醚多元醇;聚烯烃多元醇例如饱和或不饱和的聚丁二烯多元醇。
异氰酸酯:
多异氰酸酯化合物的实例包括2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、间苯二异氰酸酯、对苯二异氰酸酯、4,4′-二苯基甲烷二异氰酸酯、2,4′-二苯基甲烷二异氰酸酯、2,2′-二苯基甲烷二异氰酸酯、3,3′-二甲基-4,4′-联苯二异氰酸酯、3,3′-二甲氧基-4,4′-联苯二异氰酸酯、3,3′-二氯-4,4′-联苯二异氰酸酯、1,5-萘二异氰酸酯、1,5-四氢化萘二异氰酸酯、四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、十二亚甲基二异氰酸酯、三甲基六亚甲基二异氰酸酯、1,3-双(异氰酸基甲基)环己烷和1,4-双(异氰酸基甲基)环己烷、二甲苯二异氰酸酯、四甲基二甲苯二异氰酸酯、氢化二甲苯二异氰酸酯、赖氨酸二异氰酸酯、异佛尔酮二异氰酸酯、4,4′-二环己基甲烷二异氰酸酯、3,3′-二甲基-4,4′-二环己基甲烷二异氰酸酯、其异构体、和/或其组合。
第一表面活性剂
第一表面活性剂可以占小于6重量%;例如,第一表面活性剂可以占4至6重量%。示例性的第一表面活性剂包括但不限于,二羟甲基丙酸、二羟甲基丙酸、二羟甲基丁酸、和二氨基磺酸盐/酯。
溶剂
溶剂可以是任何溶剂;例如,溶剂可以是有机溶剂。示例性的溶剂包括但不限于一缩二丙二醇二甲基醚,其可以商业名称PROGLYDEDMM商购自The Dow Chemical Company,和二缩三丙二醇二甲基醚。另外的溶剂可以包括丙酮、甲基乙基酮、甲苯、四氢呋喃(THF)。
另外的溶剂包括但不限于丙二醇甲基醚乙酸酯、一缩二丙二醇甲基醚乙酸酯、丙二醇二乙酸酯、一缩二丙二醇二甲基醚、二甘醇正丁醚乙酸酯、乙二醇正丁醚乙酸酯。
预聚物:
所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物。用于本发明的聚氨酯预聚物可以通过任何常规的已知方法生产,例如,溶液法、热熔体法、或聚氨酯预聚物混合法,例如,在间歇或连续法中生产。而且,氨酯预聚物可以,例如,经使多异氰酸酯化合物与含活性氢的化合物(即,一种或多种基于天然油的多元醇)反应的方法制备,并且其实例包括使多异氰酸酯化合物与一种或多种基于天然油的多元醇在有机溶剂中反应,然后任选地移除溶剂的方法。在一种实施方式中,所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种第一表面活性剂的存在下与一种或多种异氰酸酯的反应产物。在一种实施方式中,预聚物不含N-甲基吡咯烷酮(NMP)。
例如,所述多异氰酸酯化合物可以与溶解在有机溶剂中的一种或多种基于天然油的多元醇在以下条件下反应:反应温度为约20℃至约150℃;在可替换的实施方式中,为30℃至130℃;异氰酸酯基团与活性氢基团的当量比为,例如,1.1∶1至3∶1,在可替换的实施方式中,为1.2∶1至2∶1。在可替换的实施方式中,预聚物可以使用过量的活性氢基团制备从而促进产生端基为羟基的聚合物。
源自有机溶剂中的一种或多种基于天然油的多元醇的聚氨酯预聚物可以在一种或多种反应性或非反应性的烯键式不饱和单体的存在下制备。这样的单体可以进一步聚合从而得到混合的聚氨酯分散体。
聚氨酯预聚物可以进一步包括一个或多个离子基团。用于制备这种具有离子基团的预聚物的官能部分包括磺酸二醇,例如,3-(2,3-二羟基丙氧基)-1-丙烷-磺酸;磺基多羧酸,例如,磺基间苯二甲酸,磺基琥珀酸;和氨基磺酸,例如2-氨基乙烷磺酸和3-氨基丙烷磺酸;氨基磺酸二醇,例如,N,N-双(2-羟基烷基)氨基磺酸(C1至C6烷基),或其环氧烷烃(AO)例如环氧乙烷和环氧丙烷的加成物,N,N-双(2-羟基-乙基)氨基磺酸;双(2-羟基乙基)磷酸酯;二羟烷基链烷酸C6至C24,例如,2,2-二羟甲基丙酸,2,2-二羟甲基丁酸,2,2-二羟甲基庚酸,2,2-二羟甲基辛酸;和氨基酸,例如,2-氨基乙酸;以及它们的盐,例如,胺例如三乙胺、链烷醇胺、吗啉的盐,和/或碱金属盐例如钠盐。包含阳离子基团的实例包括但不限于,含季铵碱的二醇、含叔铵基团的二醇及其盐。
聚氨酯预聚物还可以包括亲水基团。本申请使用的术语“亲水基团”是指阴离子基团(例如,羧基、磺酸基、或磷酸基),或阳离子基团(例如,叔氨基、或季氨基),或非离子亲水基团(例如,由环氧乙烷的重复单元组成的基团,或由环氧乙烷的重复单元和另一种环氧烷烃的重复单元组成的基团)。
在亲水基团中,包含环氧乙烷的重复单元的非离子亲水基团可以,例如,是优选的,因为最终得到的聚氨酯乳液具有优越的与其它类型的乳液的相容性。引入羧基和/或磺酸基可以有效地使颗粒大小更细。
当离子基团是阴离子基团时,用于中和的中和剂包括,例如可以使用非挥发性碱例如氢氧化钠和氢氧化钾;和挥发性碱例如叔胺(例如,三甲胺、三乙胺、二甲基乙醇胺、甲基二乙醇胺、和三乙醇胺)和氨。
当离子基团是阳离子基团时,可用的中和剂包括,例如,无机酸例如盐酸、硫酸、和硝酸;和有机酸例如甲酸和乙酸。
中和可以在含离子基团的聚氨酯预聚物发生聚合之前、过程中或之后进行。中和可以通过将中和剂直接添加到聚氨酯预聚物中或通过将中和剂在制备聚氨酯分散体的过程中添加到水相中完成。
聚氨酯预聚物可以进一步经增链剂增链。制备聚氨酯的领域的普通技术人员已知的任何增链剂都可以用于本发明。这样的增链剂的分子量通常为约30至约500并且包含至少两个含活性氢的基团。多胺是优选的一类增链剂。其它物质特别是水可以用来增加链长度并且因此是针对本发明目的的增链剂。特别优选的是,增链剂是水或水与胺的混合物,所述胺例如氨化的聚丙二醇例如得自Huntsman Chemical Company的JEFFAMINE D-400、氨基乙基哌嗪、2-甲基哌嗪、1,5-二氨基-3-甲基-戊烷、异佛尔酮二胺、乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、乙醇胺、呈其任何立体异构形式的赖氨酸及其盐、己二胺、肼和哌嗪。在本发明的实践中,增链剂可以作为增链剂在水中的溶液使用。
制备聚氨酯分散体(PUD)
根据本发明的PUD可以经间歇法或连续法生产。将聚氨酯预聚物、任选的一种或多种表面活性剂、和水进料到混合机例如OAKS混合机或IKA混合机中,从而使聚氨酯预聚物分散到水中,然后其以伯胺或仲胺增链从而形成PUD。在一种实施方式中,PUD不含N-甲基吡咯烷酮(NMP)。
在一种实施方式中,制备根据本发明的聚氨酯分散体的方法包括以下步骤:(1)提供包含一种或多种预聚物的第一流,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种第一表面活性剂的存在下与一种或多种异氰酸酯的反应产物,并且其中所述预聚物任选地由一种或多种中和剂中和;(2)提供包含水的第二流;(3)将所述第一流和所述第二流合并在一起;(4)从而形成预聚物分散体;(5)任选地中和所述预聚物分散体;(6)使所述预聚物增链;(7)从而形成所述聚氨酯分散体。
最终用途应用
根据本发明的涂布的制品包括基板;和与所述基板的一个或多个表面相连的涂层,其中所述涂层源自上文所述的本发明的聚氨酯分散体。在施用本发明的聚氨酯分散体之前,可以处理(例如,涂底漆)所述基板的一个或多个表面。所述基板可以是任何基板;例如,所述基板可以包括木材、混凝土、塑料、金属、及其组合。
在一种实施方式中,涂布的制品包括基板;和与所述基板的一个或多个表面相连的涂层,其中所述涂层源自聚氨酯分散体,所述聚氨酯分散体包含:(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水。
在另一种实施方式中,制备涂布的制品的方法包括以下步骤:(1)选择基板;(2)选择包括聚氨酯分散体的涂层组合物,其中所述聚氨酯分散体包含以下物质:(a)一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和(b)水;(3)将所述涂层组合物施用于所述基板的一个或多个表面;(4)移除至少一部分的水;(5)从而形成所述涂布的制品。
本发明的聚氨酯分散体可以经任何方法施用于基板的一个或多个表面;例如,经喷射、刷涂、浸渍、拖曳等。
本发明的聚氨酯分散体是形成膜的组合物。源自本发明聚氨酯分散体的膜的厚度可以为1μm至2mm;或者,在可替换的实施方式中,为1至500μm;或者,在可替换的实施方式中,为1至200μm;或者,在可替换的实施方式中,为1至100μm;或者,在可替换的实施方式中,为20μm至50μm。源自本发明聚氨酯分散体的膜的粘合性可以大于30%剩余;在可替换的实施方式中,大于40%剩余;在可替换的实施方式中,大于50%剩余;在可替换的实施方式中,大于60%剩余,根据ASTM D-3359测得。本发明的聚氨酯分散体的硬度发展速率可以大于或等于0.002MPa/min;在可替换的实施方式中,大于或等于0.003MPa/min;在可替换的实施方式中,大于或等于0.004MPa/min;在可替换的实施方式中,大于或等于0.005MPa/min。
在已经制备完本发明的聚氨酯分散体之后,可以将另外的溶剂添加到这样的分散体中。这样的溶剂包括但不限于丙二醇甲基醚,一缩二丙二醇甲基醚,二缩三丙二醇甲基醚,丙二醇正丙醚,一缩二丙二醇正丙醚,二缩三丙二醇正丙醚,丙二醇正苯醚,二甘醇乙基醚,二甘醇甲基醚,二甘醇正丁醚,二甘醇己基醚,乙二醇丙基醚,乙二醇正丁醚,乙二醇己基醚,三甘醇甲基醚,三甘醇乙基醚,三甘醇丙基醚,乙二醇正丁醚,乙二醇苯基醚,乙二醇正丁醚混合物,以及这些溶剂的混合物。
最终用途应用包括但不限于在任何基板上的工业和建筑涂层;所述基板例如木材、混凝土、塑料、金属、及其组合。这样的最终用途应用包括但不限于家具、地板、橱柜等。
实施例
以下实施例说明本发明但不意图限制本发明的范围。
合成NOP多元醇
天然油多元醇(NOP)由源自大豆油的脂肪酸甲酯(FAMES)在三步反应中制备。首先将FAMES加氢甲酰化为醛中间体,然后在第二步中氢化为大豆单体,如图1所示。大豆单体的平均羟基官能度大约1.0。
然后以适宜的二醇将得到的单体酯化。在该方法中,多元醇分子量同时通过单体与二醇引发剂之间的缩合以及单体之间的自缩合而增长。通过控制单体的平均官能度以及它们与二醇引发剂的比率,多元醇的分子量和平均官能度都可以被系统地控制。而且,可以调节引发剂的结构从而获得所需的性能特征或相容性。优选的二醇引发剂包含反应性伯羟基,例如1,6-己二醇和UNOXOL二醇。UNOXOLTM二醇是液态脂环族二醇,其为1,3-环己烷二甲醇和1,4-环己烷二甲醇的约50∶50混合物,即顺式和反式异构体的混合物。
预聚物的制备过程
预聚物的制备在装备有添加装置、水冷冷凝器、机械搅拌器、温度计、和氮气入口/出口管的500-mL的4颈圆底烧瓶中进行。在整个反应过程中使用氮气吹洗和500rpm的搅拌速率。油浴用作保持反应温度的加热源。在通常的预聚物制备过程中,将聚酯多元醇和二羟甲基丙酸[DMPA]添加到反应烧瓶中,然后添加异氰酸酯。首先将单独添加或作为共混物添加的多元醇加热至比所需反应温度低15-20℃的温度。当添加完多元醇和溶剂时,将反应混合物在搅拌下(200rpm)加热至所需温度(80-90℃)。当达到理论的百分比NCO时,将终产物转移至具有氮气保护层的样品容器中并用于分散体。预聚物的适宜溶剂包括丙酮、甲基乙基酮和一缩二丙二醇的二甲基醚。
合成聚氨酯分散体(PUD)
PUD在小规模(500ml)间歇法中制备,其中预聚物使用以用于预聚物的酸的化学计量量(摩尔数)的95-110%的叔胺(例如,三乙胺,TEA)中和。将预定量的水缓慢添加到预聚物中,其中预聚物与水使用产生高剪切(50,000-100,000sec-1)的特殊混合机剧烈混合。连续添加水,直至分散体的粘度降至低于~3000cP(Brookfield心轴#4,50rpm)。然后使用胺(例如,乙二胺)使分散体充分增链。最终分散体的固体含量为~35wt%,而数均粒度为~100nm。
本发明实施例1:
表1:合成PUD的配方
以上段落描述的过程和以上的配方得到所需的PUD。在将PUD涂布在不同的基板上之前,表征它们的百分比固体和粒度。使用涂料刷将在预密封的橡木制基板上制备涂层。在环境条件(50%RH和23℃)将样品干燥7天,然后测试其性质。
制备对比例2
制备对比例3
制备对比例4
制备涂层样品
使用涂料刷将在预密封的橡木制基板上制备涂层。在环境条件(50%RH和23℃)将样品干燥7天,然后测试其性质。
根据ASTM D-3359进行粘合性测量。涂层在橡木上制备并在环境条件下干燥7天,然后进行试验。交叉阴影(cross-hatch)工具用来产生100个尺寸为边长1mm见方的正方形的栅格从而测试粘合性。得自3M的剥离强度为60N/m2的透明胶带用于测试粘合性。切下一条胶带放在交叉阴影的顶端并用橡皮按压从而产生均匀的触感。在胶带粘结90秒的时间后以180度的角度扯下胶带。记录其中涂层损毁或移除的正方形的数目使用%剩余这一参数测量粘合性。表2总结该结果。
表2:根据ASTM D3359在木材上的PUD涂层的粘合性结果和使用DMA确定的硬度发展速率
*在减去4小时用于蒸发水的时间之后计算该速率。该结果基于描述的试验方法且不能外推至敞开的空气干燥。
早期硬度发展:
硬度发展通过使用动态力学波谱法测量随时间变化的模量来监控。使用改型的平行板几何结构以剪切模式进行测量。将含水PUD放入直径为25mm的铝杯中并通过相连的板挤成厚度为1mm的膜从而测量测压元件。振荡剪切测量在1Hz以基于固化程度的不同的百分比应变进行。试验在23℃和50%RH进行。在24小时的期间内,每10分钟收集数据点。与竞争者PUD以及以己二酸酯多元醇制备的PUD相比,当使用大豆多元醇和PROGLYDEDMM溶剂的组合时的硬度发展较快。结果如图2所示。它们的y轴表示以1Hz的频率和线性区域的应变速率每10分钟测量的剪切应力。起点的变化可以归因于PUD中的含水量。直线的速率或斜率给出硬度发展速率,并且可以清楚地看出,大豆PUD与PROGLYDEDMM显示出较快速率早期硬度发展。
其它实施例
样品A
将包含48.5g(800MW,0.12当量)天然油聚酯多元醇(NOP)、4g(144MW,0.06当量)UNOXOL二醇、1,3环己烷二甲醇和1,4环己烷二甲醇异构体的50/50混合物、5g(134MW,0.07当量)二羟甲基丙酸(DMPA)、25gPROGLYDEDMM溶剂(一缩二丙二醇二甲基醚)、0.01g二月桂酸二丁基锡(DBDTL)催化剂的混合物添加到装备有搅拌器、加热器、热电偶和冷凝器的夹套反应容器中并在氮气下搅拌加热至80℃。将42.5g(222MW,0.38当量)异佛尔酮二异氰酸酯(IPDI)添加到反应混合物(初始异氰酸酯与羟基含量的比率:1.5当量/当量)并在80℃保持4小时从而形成NCO含量为5.5wt%的氨基甲酸酯预聚物。将反应混合物冷却至60℃并伴随搅拌添加3.8g(101MW,0.04当量)三乙胺(TEA)从而中和DMPA的COOH基团(0.04当量)(羧基与胺含量的比率:1当量/当量)。在混合的过程中添加140g水从而形成阴离子稳定的预聚物在水中的分散体。针对增链步骤在搅拌下添加41g乙二胺(EDA,60MW,0.14当量)在水中的冷的10%溶液从而形成具有剩余NCO基团的脲连接基(异氰酸酯与胺含量的比率:0.96当量/当量)。将聚氨酯分散体(PUD)冷却至室温并确定以下性质:
外观:半透明分散体,干燥至澄清的膜
pH:8-10
密度:1.1g/cc,在25℃
粘度:500cP,在25℃
平均粒度:120nm
固体:34重量%
最小形成膜的温度:<0℃
样品B
样品B使用与样品A相同的制剂和过程制备,唯一的差别是中和(使用TEA),增链(使用EDA),和分散步骤在转子定子机械分散器而非在间歇混合机中进行。样品B的性质基本上类似于样品A。
样品C
样品C使用与样品A相同的过程制备,所不同的是多元醇组成中的下列变化:48.5g(800MW,0.12当量)天然油聚酯多元醇和4g(144MW,0.06当量)UNOXOL二醇替换为22g(0.06当量)天然油聚酯多元醇,6g(0.08当量)UNOXOL二醇和22g UNOXOL己二酸酯(884MW,0.05当量)。反应之前的NCO/OH比率无变化,为1.5。样品C的PUD物理性质基本上类似于样品A。与得自样品A的膜相比,得自样品C的膜较硬并且具有较好的耐磨性,这是因为较高含量的短链二醇和归因于聚合物硬链段含量的较高Tg的聚酯多元醇。
样品D
样品D使用与样品A相同的制剂和过程制备,所不同的是溶剂类型的下列变化:用25g的n-甲基吡咯烷酮代替25g PROGLYDE DMM。样品D的性质基本上类似于样品A。
样品E
样品E是得自Essential Industries(R-4188)的商业高固体脂族PUD,其包含9%NMP溶剂,用作圬工(masonry)类型基板的密封剂或顶涂层。PUD性质是
外观:半透明的
pH:7.6
固体:38重量%
粘度:50cP,在25℃
密度:1.05g/cc,在25℃
样品F
样品F是得自Essential Industries(R-4388)的商业不含溶剂的脂族氨基甲酸酯丙烯酸类化合物混合物,用于混凝土顶涂层应用。该性质是:
外观:半透明的
pH:7.7
固体:41重量%
粘度:<300cP,在25℃
密度:1.05g/cc,在25℃
PUD膜性能试验:
膜性能试验通过将所有的PUD样品稀释至30重量%固体进行以达到相同的膜构造。样品A、B、C、D全部形成良好的均匀无缺陷膜,而无需助溶剂,而样品E(9%NMP)&样品F(0%NMP)需要5%的另外的NMP才能形成良好品质的无缺陷膜。
粘合性试验
粘合性试验根据ASTM D 3359进行。该试验通过以下过程评估涂层膜与整洁涂底漆的基板的粘合性:在膜中形成包含1/8”交叉阴影划线(scribes)的格型切割物,将压敏胶带施用于划线的区域。扯下压敏胶带,通过计算剩余的交叉阴影正方形确定举起或移除的涂层量。在多涂层体系中重要的是确定粘合性失效是在涂层之间还是在涂层和基板之间。与底漆层或基板具有良好粘合性的涂层在胶带扯拉试验中表现的%涂层剩余的值>80%,优选为>90%,再更优选为>95%。
混凝土试验模型(blocks)
根据ASTM规范(Patio Concrete Products Inc.)进行的混凝土试验模型涂布有丙烯酸类环氧化物乳液(Quikrete 02-51730车库地板密封剂),并使其在室温空气干燥一周。然后使用样品A至F涂布涂底漆的的混凝土块。各种样品的实验测试结果展示于表1A并且显示出
●包含PROGLYDE DMM溶剂的本发明的NOP PUD样品A和B表现了非常良好的粘合性,两者都是纯的且具有低含量的外部交联剂(吖丙啶)。作为对比,使用相同制剂制备且包含NMP的NOPPUD对比样品D表现出非常差的无法接受的粘合性,两者都是纯的且具有低含量的外部交联剂(吖丙啶)。该对比样品将需要制剂中的粘合促进剂或在施用过程中的粘结层以克服该缺点;
●与以相同含量NMP溶剂制备的NOP PUD对比样品D相比,包含PROGLYDE DMM溶剂的本发明的NOP PUD样品C表现出非常良好的粘合性,两者都是纯的且具有低含量的外部交联剂(吖丙啶)。这些制剂是相当的,所不同的是聚酯多元醇(NOP,UNOXOL己二酸酯)和短链二醇(UNOXOL)的含量;
●商业PUD和WB氨基甲酸酯丙烯酸类化合物对照样品E和F(以9%和0%NMP制备,并用5%另外的用于形成良好膜的NMP溶剂配制)在呈纯形式的情况下表现出非常差的无法接受的粘合性。而且,以低含量外部交联剂(吖丙啶)试验的样品F表现出非常差的无法接受的粘合性。这些对照样品将需要制剂中的粘合促进剂或在施用过程中的粘结层以克服粘合性缺点。
表1A
耐沾污性试验
耐沾污性通过中国国家标准方法测量。将涂层施涂于白色塑料板上,在室温干燥7天,使用型号6805的BYK Gardner色度计在3处位置确定初始Y反射比。将用作代表性污垢介质的煤灰与水混合(1∶1),用软刷将0.7g该混合物作为膏剂均匀施涂在白色涂布塑料板上并在23℃,50%RH干燥2小时。将塑料板放在冲水设备的样品架上并用与水龙头相连的洒水装置冲洗1分钟,由此模拟淋雨。移动塑料板以确定所有的位置都可以被流水冲洗到。使塑料板在23℃和50%RH干燥24小时,并将以上周期总共重复5次循环。在相同位置确定塑料板的最终Y反射比,并计算平均的反射比变化(ΔY)。
●Y反射比的变化=ΔY=100*(初始Y反射比-最终Y反射比)/初始Y反射比
具有良好耐沾污性的涂层在煤灰暴露和清洗的5次循环之后表现出的反射比值的变化(ΔY)为15或更低,优选为10或更低和再更优选为5或更低。
样品的实际实验测试结果展示于表2A并且表明:
●在DPR试验中,以PROGLYDE DMM溶剂制备的本发明的NOP PUD样品(样品A、B&C)当以纯形式试验时表现出非常低的ΔY值,而当以吖丙啶交联剂试验时表现出低ΔY值。视觉上,涂布的样品在DPR试验的5次循环之后白度的变化最小;
●使用与样品A、B&C相同含量的NMP溶剂(样品D)和与样品A&B相同的制剂制备的对比NOP PUD样品当以纯形式试验时表现出低ΔY值,但当以吖丙啶交联剂试验时表现出高ΔY值。对于后一种样品,涂布的样品在DPR试验的5次循环之后白度的变化是明显值得注意的,是因为涂层上的黑色剩余物;
●以9和0%NMP溶剂制备并且用另外5%无缺陷膜的NMP溶剂配制的商业对照样品E&F以纯形式试验时表现出高ΔY值,而当以吖丙啶交联剂试验时表现出甚至更高的ΔY值。对于两种样品和在两种情况下,涂布的样品在DPR试验的5次循环之后白度的变化非常显著,是因为在涂层上保留了黑色剩余物;
●以9和0%NMP溶剂制备并用另外5%无缺陷膜的NMP溶剂配制的商业对照样品E&F以纯形式试验时表现出高ΔY值,而当以吖丙啶交联剂试验时表现出甚至更高的ΔY值。对于两种样品和在两种情况下,涂布的样品在DPR试验的5次循环之后白度的变化非常显著,是因为在涂层上保留了黑色剩余物;
表2A
纯PUD样品 | A | B | C | D | E | F |
初始反射比L | 87.57 | 87.5 | 88.4 | 87.99 | 87.13 | 90.88 |
最终反射比L | 77.95 | 78.87 | 82.05 | 77.97 | 62.05 | 75.53 |
反射比的变化ΔL | 9.62 | 8.63 | 6.35 | 10.02 | 25.08 | 15.35 |
PUD+3%吖丙啶XAMA-7交联剂样品 | A | B | C | D | E | F |
初始反射比L | 89.76 | 89.48 | 89.5 | 90.09 | 90.68 | 90.89 |
最终反射比L | 77.33 | 78.37 | 79.09 | 71.81 | 65.64 | 70.86 |
反射比的变化ΔL | 12.43 | 11.11 | 10.41 | 18.28 | 25.04 | 20.03 |
重要的是确认,溶剂类型从NMP变化至PROGLYDEDMM对由天然油多元醇贡献的PUD涂层性质例如疏水性不具有任何负面影响。耐水性试验根据ASTM D 870通过以下过程进行:将水滴(覆盖有表玻璃以防止蒸发)置于涂布样品上一段固定的时间,使水滴从表面干燥并检查涂层的任何缺陷例如变白、雾浊、溶胀、起泡或分层。涂层在室温干燥7天,然后进行试验并经受水接触2小时。表3A所示的四种NOP PUD样品的试验结果表明,水对涂层的影响非常小。结果证明,天然油多元醇对涂层性能特征的贡献例如耐水性在PUD涂层中得以保留并且与溶剂选择无关。
表3A
预期使用较低沸点溶剂例如PROGLYDEDMM(蒸发速率:0.13,相对于nBuAc=100)代替较高沸点溶剂例如NMP(蒸发速率:0.03,相对于nBuAc=100)可改善固化过程中的性质发展(例如早期耐水性、硬度发展等),这是由于溶剂从涂层中较快的挥发。但是,未预期到溶剂选择会影响固化涂层的最终的性能特征,例如粘合性和耐沾污性。由于使用较为良性的溶剂而使性能特征改善是不可预料到的,这也形成了本发明的基础。
本发明可以以不背离其精神和本质特征的其它形式实施,因此,当指明本发明的范围时,应该参考所附权利要求,而不是参考前述说明书。
Claims (4)
1.一种聚氨酯分散体,包含:
一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和
水,
其中所述基于天然油的多元醇通过选自环氧化作用、羟基化作用、臭氧分解、酯化作用、加氢甲酰化作用、和烷氧基化作用中的方法改性可再生原料资源而制备。
2.制备聚氨酯分散体的方法,包括以下步骤:
提供包含一种或多种预聚物的第一流,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物,并且其中所述预聚物任选地由一种或多种中和剂中和;
提供包含水的第二流;
将所述第一流和所述第二流合并在一起;
从而形成预聚物分散体;
任选地中和所述预聚物分散体;
使所述预聚物增链;
从而形成所述聚氨酯分散体,
其中所述基于天然油的多元醇通过选自环氧化作用、羟基化作用、臭氧分解、酯化作用、加氢甲酰化作用、和烷氧基化作用中的方法改性可再生原料资源而制备。
3.涂布的制品,包括:
基板;
与所述基板的一个或多个表面相连的涂层,其中所述涂层源自包含以下物质的聚氨酯分散体:
一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和
水,
其中所述基于天然油的多元醇通过选自环氧化作用、羟基化作用、臭氧分解、酯化作用、加氢甲酰化作用、和烷氧基化作用中的方法改性可再生原料资源而制备。
4.制备涂布的制品的方法,包括以下步骤:
选择基板;
选择包括聚氨酯分散体的涂层组合物,其中所述聚氨酯分散体包含以下物质:
一个或多个源自一种或多种预聚物的聚氨酯单元,其中所述一种或多种预聚物包括一种或多种溶解在一缩二丙二醇二甲基醚中的基于天然油的多元醇在一种或多种表面活性剂的存在下与一种或多种异氰酸酯的反应产物;和
水;
将所述涂层组合物施用于所述基板的一个或多个表面;
移除至少一部分的水;
从而形成所述涂布的制品,
其中所述基于天然油的多元醇通过选自环氧化作用、羟基化作用、臭氧分解、酯化作用、加氢甲酰化作用、和烷氧基化作用中的方法改性可再生原料资源而制备。
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6559225B1 (en) * | 1999-07-05 | 2003-05-06 | Bayer Aktiengesellschaft | Polyurethane dispersions |
EP1849810A1 (en) * | 2006-04-27 | 2007-10-31 | Cytec Surface Specialties Austria GmbH | Oil based aqueous polyurethane dispersions |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3941733A (en) | 1975-01-02 | 1976-03-02 | Minnesota Mining And Manufacturing Company | Silanol-containing urethane dispersions |
US4496487A (en) | 1982-09-07 | 1985-01-29 | Henkel Corporation | Hydroxymethyl polyols |
DE4020455A1 (de) * | 1990-06-27 | 1992-01-02 | Henkel Kgaa | Waessrige polyurethandispersion, deren herstellung und verwendung in der lederzurichtung |
ES2128549T3 (es) | 1992-12-08 | 1999-05-16 | Minnesota Mining & Mfg | Dispersiones de poliuretano terminado con silano curables a temperatura ambiente. |
CA2130604A1 (en) * | 1993-10-12 | 1995-04-13 | Han X. Xiao | Self-crosslinkable water-dispersible poly (urethane-urea) compositions |
AT409134B (de) | 1999-02-04 | 2002-05-27 | Solutia Austria Gmbh | Oxydativ trocknende polyurethandispersionen |
JP2000273138A (ja) * | 1999-03-26 | 2000-10-03 | Sekisui Chem Co Ltd | ウレタン系水性組成物 |
DE10016548A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | Polyurethan-Dispersionen |
US6465566B2 (en) | 2000-07-06 | 2002-10-15 | Omnova Solutions Inc. | Anionic waterborne polyurethane dispersions containing polyfluorooxetanes |
CA2524887C (en) | 2003-04-25 | 2012-10-02 | Dow Global Technologies Inc. | Polyurethane foams made from hydroxymethyl-containing polyester polyols |
JP2006524744A (ja) * | 2003-04-25 | 2006-11-02 | ダウ グローバル テクノロジーズ インコーポレイティド | 植物油系ポリオール及びそれから製造したポリウレタン |
DE10334753A1 (de) | 2003-07-30 | 2005-03-10 | Constr Res & Tech Gmbh | Selbstvernetzende hochmolekulare Polyurethan-Dispersion |
US20050238815A1 (en) * | 2004-04-27 | 2005-10-27 | Dvorchak Michael J | UV curable coating composition |
AU2005299520A1 (en) * | 2004-10-25 | 2006-05-04 | Dow Global Technologies, Inc. | Prepolymers made from hydroxmethyl-containing polyester polyols derived from fatty acids |
DE102007001868A1 (de) * | 2007-01-12 | 2008-07-17 | Bayer Materialscience Ag | Polyurethan-Dispersionen auf Basis von 2,2'MDI |
WO2010114643A1 (en) * | 2009-03-31 | 2010-10-07 | Dow Global Technologies Inc. | Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles |
-
2010
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6559225B1 (en) * | 1999-07-05 | 2003-05-06 | Bayer Aktiengesellschaft | Polyurethane dispersions |
EP1849810A1 (en) * | 2006-04-27 | 2007-10-31 | Cytec Surface Specialties Austria GmbH | Oil based aqueous polyurethane dispersions |
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