CN107810216B - 用于耐用的外用涂料的可交联的氟化聚氨酯添加剂 - Google Patents
用于耐用的外用涂料的可交联的氟化聚氨酯添加剂 Download PDFInfo
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- CN107810216B CN107810216B CN201680038999.6A CN201680038999A CN107810216B CN 107810216 B CN107810216 B CN 107810216B CN 201680038999 A CN201680038999 A CN 201680038999A CN 107810216 B CN107810216 B CN 107810216B
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- isocyanate
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Abstract
本发明涉及可交联的氟化聚氨酯化合物，该可交联的氟化聚氨酯化合物具有至少一个烯键式不饱和官能团。这样的化合物可用作涂料添加剂，使得当将该涂料施加到基底时，允许添加剂化合物首先迁移到表面并随后交联以形成耐用的拒油、拒污、和拒水表面。
Description
技术领域
本发明涉及可交联的氟化聚氨酯化合物，该可交联的氟化聚氨酯化合物具有至少一个烯键式不饱和官能团。这样的化合物可用作涂料添加剂，使得当将该涂料施加到基底时，允许添加剂化合物首先迁移到表面并随后交联以形成耐用的拒油、拒污、和拒水表面。
背景技术
本发明中所关注的涂料组合物包括醇酸涂料组合物、聚氨酯涂料组合物、可水分散的涂料组合物、和不饱和聚酯涂料组合物，通常为漆、透明涂料、或染色剂。以上列出的涂料组合物中的所有在干燥或固化后常常显示低十六烷接触角，易于被油润湿，并且易于脏污。涂料组合物描述于Outlines of Paint Technology(Halstead Press，纽约，NY，第三版，1990)和Surface Coatings Vol.I，Raw Materials and Their Usage(Chapman和Hall，纽约，NY，第二版，1984)中。
氟化聚氨酯丙烯酸酯涂料已经用作硬涂层的树脂。一些化合物诸如描述于
T.等人，Synthesis of Fluorinated Urethane Acrylate Based UV-CurableCoatings，Progress in Organic Coatings，76(2013)388-399中的那些，包括氟化并且烯属的官能度，以允许一旦已经将涂料施加到基底，就发生UV固化。然而，当少量用作建筑涂料的含氟添加剂时，这样的化合物设计用于或表现出提供耐积垢性。
发明内容
水基乳胶涂料基料诸如用作漆涂料的那些，具有低拒油性和不佳的可清洁性评级的趋势。为了赋予内用和外用漆表面更好的可清洁性，已经使用了包括含氟表面活性剂的小分子添加剂。然而，由于它们的小分子尺寸，添加剂不能在经受极端的环境条件影响的外用漆中提供长期性和耐用性。该添加剂可能在几天内从涂层表面洗脱。
通过引入由氟化聚氨酯构成、结合有烯键式可交联侧基的可交联化合物，本发明解决了上述问题。由于含氟添加剂的可交联性质，本发明的组合物为水基乳胶涂料提供性能及耐用性。另外，低分子量允许聚合物在交联之前迁移到涂层表面，以在涂层表面形成耐用的添加剂。本发明的聚合物赋予意料之外的期望表面效果，诸如：赋予涂层膜增大的水和油接触角、增强的耐积垢性、和增强的可清洁性。
在一个实施方案中，本发明涉及具有至少一个烯键式不饱和官能团的可交联化合物，该可交联化合物包括试剂的反应产物，该试剂包括：(a)具有至少2个异氰酸酯基团的至少一种异氰酸酯化合物、或所述化合物的混合物；(b)至少一种式(I)的全氟烷基单醇、或所述氟化单醇的混合物；
Rf-Qv-OH (I)
其中Rf为2至20个碳原子的直链或支链的全氟烷基基团，任选地间杂有一个或多个醚氧-O-、CH2、CFH、或它们的组合；Q为直链、支链或环状结构的亚烷基、亚芳基、亚芳烷基、磺酰基、砜基或亚砜基(sulfoxy)、亚磺酰氨基、亚碳酰氨基(carbonamido)、羰基氧基、亚尿烷基(urethanylene)、1，3-亚脲基、或这样的连接基团的组合；并且v为0或1；(c)至少一种异氰酸酯反应性化合物，该化合物具有一个选自OH、NH2、或SH的异氰酸酯反应性官能团并且具有至少一个烯键式不饱和基团；(d)至少一种异氰酸酯反应性化合物，该化合物具有至少一个末端羧酸和一个选自OH、NH2、或SH的异氰酸酯反应性官能团；以及(e)任选地，至少一种附加的异氰酸酯反应性化合物，该化合物选自水、烷氧基化二醇、或羟基官能的光引发剂化合物；前提条件是如果异氰酸酯化合物(a)具有2个异氰酸酯基团，则水作为附加的异氰酸酯反应性化合物(e)存在。
在另一方面，本发明涉及用于形成具有改善耐积垢性的涂层的方法，该方法包括：(i)使选自水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料的涂料基料与具有至少一个烯键式不饱和官能团的可交联化合物接触以形成涂料混合物；(ii)将该混合物施加到基底以形成涂层；(iii)允许添加剂迁移到涂层表面以形成可交联的表面涂层，以及(iv)随后使可交联的表面涂层的烯键式不饱和基团一起反应；其中该涂料混合物包含基于涂料基料和可交联化合物的总重量计约95重量％至99.98重量％的量的涂料基料和约0.02重量％至5重量％的量的可交联化合物；并且具有至少一个烯键式不饱和官能团的可交联化合物包括试剂的反应产物，该试剂包括；(a)具有至少2个异氰酸酯基团的至少一种含异氰酸酯基团的化合物、或所述化合物的混合物；(b)至少一种式(I)的全氟烷基单醇、或所述氟化单醇的混合物；
Rf-Qv-OH (I)
其中Rf为2至20个碳原子的直链或支链的全氟烷基基团，任选地间杂有一个或多个醚氧-O-、CH2、CFH、或它们的组合；Q为直链、支链或环状结构的亚烷基、亚芳基、亚芳烷基、磺酰基、砜基或亚砜基、亚磺酰氨基、亚碳酰氨基、羰基氧基、亚尿烷基、1，3-亚脲基、或这样的连接基团的组合；并且v为0或1；(c)至少一种异氰酸酯反应性化合物，该化合物具有一个选自OH、NH2、或SH的异氰酸酯反应性官能团并且具有至少一个烯键式不饱和基团；(d)至少一种异氰酸酯反应性化合物，该化合物具有至少一个末端羧酸和一个选自OH、NH2、或SH的异氰酸酯反应性官能团；以及(e)任选地，至少一种附加的异氰酸酯反应性化合物，该化合物选自水、烷氧基化二醇、或羟基官能的光引发剂化合物；前提条件是如果异氰酸酯化合物(a)具有2个异氰酸酯基团，则水作为附加的异氰酸酯反应性化合物(e)存在。
具体实施方式
本文中，所有商标均用大写字母标记。
术语“(甲基)丙烯酸类”或“(甲基)丙烯酸酯”分别指甲基丙烯酸类和/或丙烯酸类、以及甲基丙烯酸酯和/或丙烯酸酯；并且术语(甲基)丙烯酰胺指甲基丙烯酰胺和/或丙烯酰胺。
如下文所用，术语“醇酸涂料”是指基于醇酸树脂的常规液体涂料，通常为漆、透明涂料、或染色剂。醇酸树脂是含有不饱和脂族酸残基的复杂支化和交联聚酯。
如下文所用，术语“聚氨酯涂料”是指基于I型聚氨酯树脂的常规液体涂料，通常为漆、透明涂料、或染色剂。聚氨酯涂料通常包括多异氰酸酯(通常为甲苯二异氰酸酯)与干性油酸的多元醇酯的反应产物。聚氨酯涂料通过ASTM D16归类为五个类别。I型聚氨酯涂料含有最少10重量％的预反应的可自氧化粘结剂，其特征在于不存在显著量的游离异氰酸酯基团。这些也被称为聚醇酸、聚氨酯改性的醇酸、油改性的聚氨酯、聚氨酯油、或聚氨酯醇酸。I型聚氨酯涂料是最大类别的聚氨酯涂料，并且包括漆、透明涂料、或染色剂。I型聚氨酯涂料的固化涂料通过空气氧化和粘结剂中的不饱和干性油残余物的聚合反应形成。
如下文所用，术语“不饱和聚酯涂料”是指基于不饱和聚酯树脂的常规液体涂料，其溶解于单体中，并且根据需要含有引发剂和催化剂，通常作为漆、透明涂料、染色剂、或凝胶涂料制剂。
如本文所用，术语“水分散的涂料”是指旨在装饰或保护基底的表面涂料，基本上包括乳液、乳胶、或分散于水相中的成膜材料悬浮液，并且任选地含有表面活性剂、保护胶体和增稠剂、颜料和体质颜料、防腐剂、杀真菌剂、冻融稳定剂、消泡剂、控制pH的试剂、聚结助剂、以及其它成分。水分散的涂料的示例包括但不限于有颜料涂料诸如乳胶漆、无颜料涂料诸如木材密封剂、染色剂和涂饰剂、用于砖石和水泥的涂料、以及水基沥青乳液。对于乳胶漆，成膜材料为丙烯酸酯丙烯酸类、苯乙烯丙烯酸类、乙烯基-丙烯酸类、乙烯基、或它们的混合物的乳胶聚合物。这样的水分散的涂料组合物由C.R.Martens描述于“Emulsion andWater-Soluble Paints and Coatings”(Reinhold Publishing Corporation，New York，NY，1965)中。
如本文所用，术语“涂料基料”指水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料的液体制剂，其随后施加到基底以用于在所述表面上形成持久的膜。涂料基料包括存在于常规液体涂料中的那些溶剂、颜料、填料、和功能添加剂。例如，涂料基料制剂可包括分散于水中的聚合物树脂和颜料，其中所述聚合物树脂为一种丙烯酸类聚合物乳胶、乙烯基-丙烯酸类聚合物、乙烯基聚合物、I型聚氨酯聚合物、醇酸聚合物、环氧聚合物、或不饱和聚酯聚合物、或它们的混合物。
在一个实施方案中，本发明涉及具有至少一个烯键式不饱和官能团的可交联化合物，该可交联化合物包括试剂的反应产物，该试剂包括：(a)具有至少2个异氰酸酯基团的至少一种异氰酸酯化合物、或所述化合物的混合物；(b)至少一种式(I)的全氟烷基单醇、或所述氟化单醇的混合物；
Rf-Qv-OH (I)
其中Rf为2至20个碳原子的直链或支链的全氟烷基基团，任选地间杂有一个或多个醚氧-O-、CH2、CFH、或它们的组合；Q为直链、支链或环状结构的亚烷基、亚芳基、亚芳烷基、磺酰基、砜基或亚砜基、亚磺酰氨基、亚碳酰氨基、羰基氧基、亚尿烷基、1，3-亚脲基、或这样的连接基团的组合；并且v为0或1；(c)至少一种异氰酸酯反应性化合物，该化合物具有一个选自OH、NH2、或SH的异氰酸酯反应性官能团并且具有至少一个烯键式不饱和基团；(d)至少一种异氰酸酯反应性化合物，该化合物具有至少一个末端羧酸和一个选自OH、NH2、或SH的异氰酸酯反应性官能团；以及(e)任选地，至少一种附加的异氰酸酯反应性化合物，该化合物选自水、烷氧基化二醇、或羟基官能的光引发剂化合物；前提条件是如果异氰酸酯化合物(a)具有2个异氰酸酯基团，则水作为附加的异氰酸酯反应性化合物(e)存在。
作为具有至少2个异氰酸酯基团的至少一种异氰酸酯化合物(a)，主要具有两个或更多个异氰酸酯基团的任何二异氰酸酯或多异氰酸酯适用于本发明。例如，六亚甲基二异氰酸酯均聚物适用于本文并且可商购获得。应认识到，微量二异氰酸酯可保留在具有多个异氰酸酯基团的产物中。这方面的示例为含有少量六亚甲基二异氰酸酯残余的双缩脲。
也适于用作多异氰酸酯反应剂的是烃二异氰酸酯-衍生的异氰尿酸酯三聚体。一种具体的化合物是DESMODUR N-100(基于六亚甲基二异氰酸酯的化合物，其得自美国宾夕法尼亚州匹兹堡拜耳公司(Bayer Corporation，Pittsburgh，PA))。对于本发明而言可用的其它三异氰酸酯是通过反应三摩尔甲苯二异氰酸酯获得的那些。甲苯二异氰酸酯的异氰脲酸酯三聚体和3-异氰酸基甲基-3，4，4-三甲基环己基异氰酸酯的异氰脲酸酯三聚体是可用于本发明目的的三异氰酸酯的其它示例，正如甲烷-三-(苯基异氰酸酯)。多异氰酸酯的前体诸如二异氰酸酯在本发明中也适于用作多异氰酸酯的基底。得自美国宾夕法尼亚州匹兹堡拜耳公司(Bayer Corporation，Pittsburgh，PA)的DESMODUR N-3300、DESMODUR N-3600、DESMODUR Z-4470、DESMODUR H、DESMODUR N3790和DESMODUR XP 2410以及双-(4-异氰酸根合环己基)甲烷也适用于本发明中。优选的多异氰酸酯反应物是含有缩二脲结构的脂族和芳族多异氰酸酯，或含有异氰酸酯的聚二甲基硅氧烷。这样的多异氰酸酯还可含有脂族和芳族取代基二者。
六亚甲基二异氰酸酯均聚物可以商品名DESMODUR N-100、DESMODUR N-75和DESMODUR N-3200从美国宾夕法尼亚州匹兹堡拜耳公司(Bayer Corporation，Pittsburgh，PA)商购获得；3-异氰酸基甲基-3，4，4-三甲基环己基异氰酸酯，可以商品名DESMODUR I从拜耳公司(Bayer Corporation)商购获得；双-(4-异氰酸环己基)甲烷，可以商品名DESMODUR W从拜耳公司(Bayer Corporation)商购获得；并且式(IIa)、(IIb)、(IIc)、(IId)、和(IIe)的二异氰酸酯三聚体是可用的：
二异氰酸酯三聚体(IIa-e)可以商品名例如DESMODUR Z4470、DESMODUR IL、DESMODUR N-3300和DESMODUR XP2410分别从拜耳公司(Baver Corporation)获得。
可将氟化醇掺入可交联的聚氨酯化合物，作为至少一种全氟烷基单醇化合物(b)以改善最终产物的去污特性。可使用任何合适的氟化醇，包括式(I)的氟化醇。在式(I)中，Rf和Q可为直链或支链的。在一个方面，氟化醇为基于调聚物的醇，其中Rf为直链全氟烷基基团，v为1，并且Q为直链亚烷基基团。在一个方面，Rf为C1至C6直链或支链的全氟烷基基团，v为1，并且Q为直链或支链的C1至C6亚烷基基团。在一个实施方案中，Q为1至4个碳原子的直链或支链的亚烷基，并且在第二实施方案中，Q为2至4个碳原子的直链或支链的亚烷基。也可使用氟化单体的混合物。
合适的氟化醇包括但不限于C4F9SO2NH(CH2)3OH、C6F13SO2NH(CH2)3OH、C8F17SO2NH(CH2)3OH、C4F9SO2NH(CH2)2OH、C6F13SO2NH(CH2)2OH、C8F17SO2NH(CH2)2OH、C4F9SO2N(CH3)(CH2)2OH、C6F13SO2N(CH3)(CH2)2OH、C8F17SO2N(CH3)(CH2)2OH、C4F9CH2CF2SO2NH(CH2)3OH、C3F7OCF2CF2SO2NH(CH2)3OH、C4F9CH2CH2CF2CF2SO2NH(CH2)3OH、C4F9OCFHCH2CH2SO2NH(CH2)3OH、C4F9SO2CH2CH2NH(CH2)3OH、C6F13SO2CH2CH2NH(CH2)3OH、C8F17SO2CH2CH2NH(CH2)3OH、C4F9CH2CH2SO2NHCH2CH2OH、C6F13CH2CH2SO2NHCH2CH2OH、C8F17CH2CH2SO2NHCH2CH2OH、C4F9CH2CH2SO2N(CH3)CH2CH2OH、C6F13CH2CH2SO2N(CH3)CH2CH2OH、C8F17CH2CH2SO2N(CH3)CH2CH2OH、C4F9(CH2)2OH、C6F13(CH2)2OH、C8F17(CH2)2OH、C4F9OH、C6F13OH、C8F17OH、C4F9CH2CH2CH2OH、C6F13CH2CH2CH2OH、C4F9CH2OH、C6F13CH2OH、C4F9CH2CF2CH2CH2OH、C6F13CH2CF2CH2CH2OH、C4F9CH2CF2CH2CF2CH2CH2OH、C6F13CH2CF2CH2CF2CH2CH2OH、C3F7OCF2CF2CH2CH2OH、C2F5OCF2CF2CH2CH2OH、CF3OCF2CF2CH2CH2OH、C3F7(OCF2CF2)2CH2CH2OH、C2F5(OCF2CF2)2CH2CH2OH、CF3(OCF2CF2)2CH2CH2OH、C3F7OCHFCF2OCH2CH2OH、C2F5OCHFCF2OCH2CH2OH、CF3OCHFCF2OCH2CH2CH2OH、C3F7OCHFCF2OCH2CH2CH2OH、C2F5OCHFCF2OCH2CH2CH2OH、CF3OCHFCF2OCH2CH2OH、C4F9CH2CH2SCH2CH2OH、C6F13CH2CH2SCH2CH2OH、C4F9SCH2CH2OH、C6F13SCH2CH2OH、C4F9CH2CH2CF2CF2CH2CH2OH、C3F7OCF(CF3)C(O)NHCH2CH2OH、C3F7OCF(CF3)C(O)N(CH3)CH2CH2OH、C4F9NHC(O)NHCH2CH2OH、C6F13NHC(O)NHCH2CH2OH、HCF2(CF2)4CH2OH、HCF2(CF2)6CH2OH、HCF2(CF2)8CH2OH、其类似的变型、以及它们的混合物。
具有至少一个异氰酸酯反应性基团和至少一个烯键式不饱和基团的合适的异氰酸酯反应性化合物(c)包括具有任何异氰酸酯反应性官能团诸如OH、NH2、或SH的化合物。在一个实施方案中，异氰酸酯反应性烯键式不饱和化合物(c)选自羟烷基乙烯基化合物、含有2至30个碳的烷基链并且具有1至15个烯属单元的直链或支链的醇、烯丙基或甲基烯丙基聚醚醇、氨基烷基乙烯基化合物、丙烯酸类或甲基丙烯酸类烷基醇、丙烯酸类或甲基丙烯酸类聚醚醇、或丙烯酸类或甲基丙烯酸类胺。具体示例包括但不限于聚(乙二醇)烯丙基醚、包括二烯丙基醇的烯丙醇、(甲基)丙烯酸羟乙酯、(甲基)丙烯酸羟丙酯、(甲基)丙烯酸羟丁酯、乙氧基化(甲基)丙烯酸酯、油酸、亚油酸、蓖麻油酸、芥酸、棕榈油酸、异油酸、二十碳烯酸、反油酸、eurucicic酸、神经酸、松油酸、花生四烯酸、二十碳五烯酸、二十二碳六烯酸、二十碳二烯酸、二十二碳四烯酸、以及它们的混合物。在一个实施方案中，异氰酸酯反应性化合物(c)具有至少两个烯键式不饱和基团。一些示例包括但不限于二烯丙基醇和三羟甲基丙烷二烯丙基醚。
合适的异氰酸酯反应性化合物(d)具有至少一个末端羧酸和一个异氰酸酯反应性官能团，其包括具有任何异氰酸酯反应性官能团诸如OH、NH2、或SH的化合物。示例包括但不限于羟基乙酸、羟基丙酸、聚乙酸、聚乳酸、羟基辛酸、羟基癸酸、羟基月桂酸、羟基肉豆蔻酸、羟基棕榈酸、羟基硬脂酸、羟基花生酸、羟基二十二烷酸、羟基二十四烷酸、羟基棕榈油酸、羟基亚油酸、羟基花生四烯酸、羟基油酸、或羟基芥酸。优选的示例包括但不限于羟基乙酸、羟基丙酸、和聚乳酸。这样的化合物可有助于改善分散稳定性。最终的聚氨酯化合物具有羧酸侧基，其可用碱诸如氨在用作涂料添加剂之前进一步中和。
任选的附加异氰酸酯反应性化合物(e)可包括诸如水、烷氧基化二醇、或羟基官能的光引发剂化合物。其中异氰酸酯化合物(a)仅含有2个异氰酸酯官能团，存在一种交联化合物诸如水以允许结合所有三种异氰酸酯反应性化合物(b)、(c)、和(d)。
也可掺入烷氧基化二醇作为化合物(e)以改善分散稳定性。这样的化合物可包括例如-(CH2CH2O)s(CH(CH3CH2O)t-H或(C(O)-O-(CH2CH2O)s(CH(CH3)CH2O)tH的嵌段，其中s和t为0至50的整数。在该实施方案中，-(CH2CH2O)-表示氧乙烯基团(EO)，而-(CH(CH3)CH2O)-表示氧丙烯基团(PO)。这些聚醚可仅含有EO基团、仅含有PO基团，或含有它们的混合物。这些聚醚还可作为表示为PEG-PPG-PEG(聚乙二醇-聚丙二醇-聚乙二醇)的三嵌段共聚物存在。在一个方面，烷氧基化二醇具有等于或大于约200的平均分子量。在另一方面，该平均分子量介于350和2000之间。
当使用羟基官能的光引发剂化合物时，一旦可交联的聚氨酯化合物已经迁移到涂层表面，它们就用来引发固化。因为光引发剂与可交联的聚氨酯化合物共价结合，它们已经存在于期望的交联位点处。
这些可交联化合物优选地为含水组合物的一部分，但还可包含选自有机溶剂的溶剂。含水组合物可为含水溶液、含水乳液或含水分散体的形式。在一个实施方案中，可一步制得可交联化合物。在另一个实施方案中，合成可按顺序完成。当使用多官能的化合物诸如水或烷氧基化二醇时，按顺序添加是尤其有用的。在这种情况下，使用的异氰酸酯反应性化合物(b)、(c)、和(d)的摩尔浓度使得仍然有未反应的异氰酸酯基团与化合物(e)反应。在一个实施方案中，化合物(b)的用量为10摩尔％至89摩尔％，在另一个实施方案中，用量为30摩尔％至78摩尔％，并且在第三实施方案中，30摩尔％至70摩尔％。在一个方面，化合物(c)的用量为1摩尔％至25摩尔％，在另一个实施方案中，1摩尔％至15摩尔％，并且在第三实施方案中，1摩尔％至10摩尔％。在一个实施方案中，化合物(d)的用量为10摩尔％至80摩尔％，在另一个实施方案中，用量为20摩尔％至68摩尔％，并且在第三实施方案中，20摩尔％至60摩尔％。在一个实施方案中，化合物(e)的用量为0摩尔％至25摩尔％，在另一个实施方案中，1摩尔％至20摩尔％，并且在第三实施方案中，1摩尔％至10摩尔％。所有摩尔％量基于异氰酸酯反应性化合物的总摩尔数。
这种反应通常通过将化合物(a)至(d)、以及任选的附加异氰酸酯反应性化合物(e)装入反应容器来进行。试剂添加的顺序不是关键的，但是如果使用水，则水应在一种或多种异氰酸酯和化合物(b)、(c)、和(d)之后添加。所装入的反应物的具体重量基于它们的当量以及反应容器的工作容量，并且被调节成使得取代的糖醇将在第一步骤中被消耗掉。通常使用不含异氰酸酯反应性基团的合适的干燥有机溶剂作为溶剂。酮是优选的溶剂，并且为了便利性和可用性，甲基异丁基酮(MIBK)是特别优选的。搅拌装入物，并且温度调节成约40℃至70℃。典型地，然后通常以基于组合物的干重计约0.01重量％至约1.0重量％的量将催化剂诸如氯化铁(III)添加到有机溶剂中，并且温度升高至约80℃至100℃。还可使用助催化剂，诸如碳酸钠。如果添加了水，则进行初始反应，使得小于100％的异氰酸酯基团反应。在保持数小时后的第二步中，加入附加的溶剂、水和任选的第二化合物。在一个实施方案中，允许混合物再反应数小时，或直到所有异氰酸酯已被反应。然后可加入附加的水和表面活性剂(如果需要)用于分散目的，并且搅拌直至充分混合。均化或超声处理步骤之后，可通过减压蒸发除去有机溶剂。对于本领域的技术人员将显而易见的是，还可使用对任何或全部上述过程的多种变化，以将获得最高收率、生产率或产品质量的反应条件最优化。
如上所述制得的含氟聚合物组合物可直接用于涂料组合物，或者可加入附加溶剂(“施加溶剂”)以获得期望的固含量。施加溶剂通常是选自醇和酮的溶剂。含氟聚合物组合物可用作涂料添加剂，其中可将含氟聚合物组合物加入施加到基底的涂料基料中。当将该涂料施加到基底时，允许添加剂化合物首先迁移到表面并随后交联以形成耐用的拒油、拒污、和拒水表面。
因此，本发明涉及一种组合物，该组合物包含(a)选自水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料的涂料基料；和(b)可交联添加剂，其中该可交联添加剂为如上所述的可交联化合物；其中该组合物包含基于(a)和(b)的总重量计约95重量％至99.98重量％的量的(a)和约0.02重量％至5重量％的量的(b)。
如上所述，涂料基料为水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料的液体制剂，其随后施加到基底以用于在所述表面上形成持久的膜。在一个实施方案中，涂料基料包括具有侧羟基或侧羧酸基的聚合物。涂料基料包括存在于常规液体涂料中的那些溶剂、颜料、填料、和功能添加剂。通常涂料基料可包括10重量％至60重量％的树脂化合物，0.1重量％至80重量％的功能添加剂(包括颜料、填料、和其它添加剂)，并且涂料基料组合物的剩余部分为水或溶剂。对于建筑涂料，树脂化合物的量为约30重量％至60重量％，功能添加剂(包括颜料、扩充剂、填料、和其它添加剂)的量为0.1重量％至60重量％，并且剩余部分为水或溶剂。
涂料组合物还可包含附加组分以向所得涂料提供表面效果。例如，组合物还可包含非聚合的烯键式不饱和可交联化合物，用于为可交联聚合物化合物提供附加的交联位点。在一个实施方案中，这种非聚合的可交联化合物为脂肪酸化合物，其量为基于涂料基料、可交联化合物、和脂肪酸的总重量计约0.001重量％至1重量％。可使用任何脂肪酸，包括油酸、亚油酸、蓖麻油酸、芥酸、棕榈油酸、异油酸、二十碳烯酸、反油酸、eurucicic酸、神经酸、(松油酸、花生四烯酸、二十碳五烯酸、二十二碳六烯酸、二十碳二烯酸、二十二碳四烯酸、以及它们的混合物。涂料组合物也可包括固化引发剂(包括光引发剂)，其作为涂料基料制剂的一部分或者作为附加的添加剂。
涂料组合物也可包含颜料。这样的颜料可为涂料基料制剂的一部分，或者可随后加入。任何颜料可用于本发明。如本文所用，术语“颜料”意指在使用中为颗粒状且基本上不挥发的透明和不透明成分。如本文所用，颜料包括标记为颜料的成分，也包括通常在涂料商标中标记为惰性物质、扩充剂、填料、和类似物质的成分。
可用于本发明的代表性的颜料包括但不限于金红石和锐钛矿TiO2、粘土诸如高岭土、石棉、碳酸钙、氧化锌、氧化铬、硫酸钡、氧化铁、氧化锡、硫酸钙、滑石、云母、硅石、白云石、硫化锌、氧化锑、二氧化锆、二氧化硅、硫化镉、硒化镉、铬酸铅、铬酸锌、钛酸镍、硅藻土、玻璃纤维、玻璃粉、玻璃球、单星蓝G(C.I.颜料蓝15)、钼橙(C.I.颜料红104)、甲苯胺红YW(C.I.颜料3)-过程聚集晶体、酞菁蓝(C.I.颜料蓝15)-醋酸纤维素分散体、甲苯胺红(C.I.颜料红3)、色淀红BW(C.I.颜料红48)、甲苯胺黄GW(C.I.颜料黄1)、单星蓝BW(C.I.颜料蓝15)、单星绿BW(C.I.颜料绿7)、颜料猩红(C.I.颜料红60)、金棕(C.I.颜料棕6)、单星绿G(C.I.颜料绿7)、单星褐红B、单星橙、和酞菁绿GW 951。
二氧化钛(TiO2)是本发明使用的优选颜料。用于本发明的二氧化钛颜料可为金红石或锐钛矿结晶形式。其一般通过氯化物方法或硫酸盐方法制得。在氯化物方法中，TiCl4被氧化为TiO2颗粒。在硫酸盐方法中，将硫酸和含钛的矿石溶解，然后所得溶液经过一系列步骤产生TiO2。硫酸盐和氯化物方法均更详细地描述于John Wiley&Sons，NY(1988)，“ThePigment Handbook”，第2版第1卷中，其中的教导内容以引用方式并入本文。
当用作涂料基料的添加剂时，通过例如将含氟聚合物组合物与涂料基料混合，经由充分接触而将可交联聚合物化合物有效地引入到涂料基料中。可例如并且方便地在环境温度下执行含氟聚合物与涂料基料的接触。可采用更复杂的接触或混合方法，诸如使用机械摇动器或提供热量。这样的方法一般不必要，并且一般不显著改善最终的涂料组合物。
当用作涂料基料的添加剂时，本发明的组合物一般按含氟聚合物干重相对于湿漆重量的重量百分比计约0.02重量％至约5重量％加入。在一个实施方案中，使用约0.02重量％至约0.5重量％，并且在第三实施方案中，将约0.05重量％至约0.25重量％的可交联聚合物化合物加入到漆中。
在另一个实施方案中，本发明涉及用于形成具有改善耐积垢性的涂层的方法，该方法包括：(i)使选自水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料的涂料基料与具有至少一个烯键式不饱和官能团的可交联化合物接触以形成涂料混合物；(ii)将该混合物施加到基底以形成涂层；(iii)允许添加剂迁移到涂层表面以形成可交联的表面涂层，以及(iv)随后使可交联的表面涂层的烯键式不饱和基团一起反应；其中该涂料混合物包含基于涂料基料和可交联化合物的总重量计约95重量％至99.98重量％的量的涂料基料和约0.02重量％至5重量％的量的可交联化合物；并且具有至少一个烯键式不饱和官能团的可交联化合物包括试剂的反应产物，该试剂包括：(a)具有至少2个异氰酸酯基团的至少一种异氰酸酯化合物、或所述化合物的混合物；(b)至少一种式(I)的全氟烷基单醇、或所述氟化单醇的混合物；
Rf-Qv-OH (I)
其中Rf为2至20个碳原子的直链或支链的全氟烷基基团，任选地间杂有一个或多个醚氧-O-、CH2、CFH、或它们的组合；Q为直链、支链或环状结构的亚烷基、亚芳基、亚芳烷基、磺酰基、砜基或亚砜基、亚磺酰氨基、亚碳酰氨基、羰基氧基、亚尿烷基、1，3-亚脲基、或这样的连接基团的组合；并且v为0或1；(c)至少一种异氰酸酯反应性化合物，该化合物具有一个选自OH、NH2、或SH的异氰酸酯反应性官能团并且具有至少一个烯键式不饱和基团；(d)至少一种异氰酸酯反应性化合物，该化合物具有至少一个末端羧酸和一个选自OH、NH2、或SH的异氰酸酯反应性官能团；以及(e)任选地，至少一种附加的异氰酸酯反应性化合物，该化合物选自水、烷氧基化二醇、或羟基官能的光引发剂化合物；前提条件是如果异氰酸酯化合物(a)具有2个异氰酸酯基团，则水作为附加的异氰酸酯反应性化合物(e)存在。
本发明的涂料组合物可用于向多种基底提供保护性和/或装饰性涂层。这样的基底主要包括构造材料和硬质表面。基底优选地选自木材、金属、墙板、砖石、混凝土、纤维板和纸材。也可使用其它材料作为基底。
本发明的涂料可用于处理基底，通过将基底与包含涂料基料和式(I)聚合物组合物的涂料组合物接触，并将涂料组合物干燥或固化在基底上，从而处理基底。可使用任何使涂料组合物接触基底的方法。这样的方法是本领域技术人员熟知的，诸如刷涂、喷雾、辊涂、刮涂、擦拭、浸蘸、泡沫、液体注射、浸没或浇铸。在将涂料施加到基底后，使用任何常规方法使聚合物化合物聚合，包括允许添加剂在空气中通过氧化固化来交联。也可采用辐射固化，包括UV固化。固化引发剂和添加剂可与涂料组合物混合以改善固化效率。
本发明的组合物为涂料提供性能以及耐用性。它们赋予意料之外的期望表面效果，诸如：赋予涂层膜增大的水和油接触角、增强的耐积垢性、和增强的可清洁性。出于这些原因，本发明的化合物尤其适于用作外用涂料和漆的添加剂。
材料和测试方法
除非另外指明，否则所有溶剂、单体和试剂均购自西格玛奥德里奇公司(Sigma-Aldrich)，并且按供应的原样直接使用。DESMODUR N3300得自拜耳材料科学公司(BayerMaterial Science LLC)。IRGACURE 2959是一种羟基官能的光引发剂，得自BASF。1H，1H，2H，2H-全氟辛醇得自E.I.DuPont de Nemours&Co，Wilmington，DE。
测试方法
油漆中可交联的聚氨酯添加剂的定量投料和测试板施加
将本发明的含氟丙烯酸共聚物的含水分散体以350ppm的氟含量加入选定的市售内用和外用乳胶漆中，在定量投料之前，该内用和外用乳胶漆不含氟添加剂。使用顶置式考尔斯叶片搅拌器(Cowles Blade stirrer)在600rpm下混合样品10分钟。然后将混合物转移至玻璃瓶，密封并置于辊式开炼机上过夜，以允许含氟聚合物均匀混合。然后使用5mL伯德式涂膜器(bird-applicator)经由BYK-Gardner刮涂装置将样品均匀刮涂在黑色Leneta
卡(5.5″×10″)或铝Q-板(4″×12″)上。然后将漆膜在室温下干燥7天。
测试方法1：经由接触角测量评估拒油性
使用油接触角测量来测试含氟添加剂向漆膜表面的迁移。通过测角计在涂覆有干燥漆膜的Leneta板的1英寸测试带上进行油接触角测试。
使用Ramé-Hart 200型标准自动测角计，该测角计采用DROP image标准软件并且配备有250ul注射器的自动分配体系和带照明的标本台组件。测角计相机通过接口与计算机连接，从而允许在计算机屏幕上能够观察到液滴。使用该软件，可在计算机屏幕上独立调节水平轴线和正交线。
在测量接触角之前，将样品置于样品台上并调节竖直游标以对齐目镜的水平线(轴线)，与样品的水平面重合。定位该台相对于目镜的水平位置以便观察样品界面处测试流体液滴界面区的一侧。
为测定测试流体在样品上的接触角，使用30μL的吸移管尖头和自动分配体系转移校准量的测试流体，将大约一滴测试流体分配到样品上。对于油接触角测量，十六烷是适用的。在200型情况下，在经由样品台调节使样品水平后，经由软件调节水平线和正交线，并且计算机基于建模液滴外观来计算接触角。初始接触角是将测试流体分配到样品表面上后立即测得的角度。大于30度的初始接触角是有效拒油性的标志。
测试方法2：外用油漆的耐积垢性(DPR)测试
DPR测试用于评估涂漆板防止积垢的能力。人造干垢由硅胶(38.7％)、氧化铝粉末(38.7％)、黑色氧化铁粉末(19.35％)和灯黑粉末(3.22％)构成，其用于这一测试。混合灰尘组分并置于辊上48小时以进行充分混合，并且存储在干燥箱中。
将外用油漆样品刮涂在铝Q-板上，该板切成1.5″×2″的大小，并且将这些样品的四个平行测定样用胶带贴在4″×6″的金属板上。使用Hunter Lab色度计测量每个Q-板的初始白度(L*初始)。然后将4”×6”的金属板插入在木块中的45度角的狭槽内。灰尘施加器装有金属网片，其将灰尘分配在板上，直至该板完全覆盖灰尘。然后通过轻敲安装在浅盘内部的木块上的板5次，去除过多的灰尘。然后将保持积尘的板上的4″×6″板夹在Vortex-Genie2上60秒，以去除任何剩余的灰尘。然后移除该板，并且敲击10次以去除任何剩余的灰尘。使用相同的色度计再次测量每个1.5”×2”样品的白度(L*积尘的)，记录用灰尘处理之前和之后的白度差值。将该值取平均值。DPR以ΔL*表示，其中ΔL*＝(L*初始-L*积尘的)。较低的ΔL*值指示较好的耐积垢性。
测试方法3：水洗耐用性(油接触角)
将外用油漆样品刮涂在铝Q-板上，该板切成1.5″×2″的大小，固定成45°角，并且设定用流动水以1L/分钟的流速洗涤五分钟。将样品风干7天，然后如测试方法1所述测量油接触角。
测试方法4：DPR和油接触角耐用性的耐候性(WOM)
涂覆的Q-板的加速风化在ATLAS Ci5000氙灯Weather-o-Meter中进行。氙灯配备有S型Boro Inner和Outer Filters。耐候性循环根据D6695，循环2进行。在风化周期中，板经受重复的2-小时程序，其包括18分钟的光照和水喷雾，随后仅进行102分钟的光照。在整个程序期间，板保持在63℃并且在仅UV时段，相对湿度保持在50％。
对于24-小时的WOM程序，允许刚刚涂覆的铝Q-板风干7天。使用Hunter Lab色度计测量每个Q-板的初始白度(L*初始)。一组板经受DPR测试(按照测试方法2)以及油和水接触角测试(按照测试方法1)。将同样一组板置于weather-o-meter中，并且根据上文所述允许其经受12个连续的2-小时循环。在完成风化循环后，将板干燥，根据测试方法1和2进行评估，并且再次经受DPR。
实施例1
将DESMODUR N3300(6.68g)加到带有磁力搅拌棒的圆底烧瓶中，其保持在N2气氛下。加入甲基异丁基酮(MIBK)(10.9g)，1H，1H，2H，2H-全氟辛醇(4.16g，11.44mmol)，乙醇酸(0.74g，9.7mmol)，聚(乙烯乙二醇)单甲基丙烯酸酯(MW 526，3.1g，5.89mmol)，三羟甲基丙烷二烯丙基醚(1.40g，5.89mmol)和IRGACURE 2959(0.39g，1.73mmol)。将反应混合物加热至60℃并装入在MIBK(0.7g)中的催化剂二月桂酸二丁基锡(0.02g)。然后将反应混合物加热至90℃，持续12小时。反应混合物变成粘稠黄色液体。然随后将混合物冷却至50℃。然后加入NH4OH(0.59g，9.7mmol NH3)在H2O(38mL)中的中和溶液。在pH约10下形成白色浆液，然后将内容物在50℃下加热搅拌30分钟。取样品进行固体重量百分比分析，并且测定为14.6重量％。将计算量的这种分散体(350ppm F)加到外用测试漆的样品中，并且按照所述测试方法评估刮涂板。
实施例2
将DESMODUR N3300(3.86g)加到带有磁力搅拌棒的圆底烧瓶中，其保持在N2气氛下。加入MIBK(16.5g)，1H，1H，2H，2H-全氟辛醇(2.18g，6.0mmol)，2，2-双(二羟甲基)丙酸(1.6g，12.0mmol)和聚(乙烯乙二醇)单甲基丙烯酸酯(Mw 526，0.84g，1.6mmol)，随后加入催化剂二月桂酸二丁基锡(0.013g)。然后将反应加热至90℃，持续四小时。加入水(16.5g)和浓NH4OH(0.83g，13.63mmol NH3)，并且将反应加热至90℃，持续3小时，从而获得白色分散体。减压蒸发溶剂，获得聚氨酯分散体，它是一种白色浆液。取样品进行固体重量百分比分析(23重量％)。将计算量的这种分散体(350ppm F)加到外用测试漆的样品中，并且按照所述测试方法评估刮涂板。
实施例3
将DESMODUR N3300(1153.85g)加到带有机械搅拌的反应器中，其保持在N2气氛下。加入甲基异丁基酮(MIBK)(3693.88g)，1H，1H，2H，2H-全氟辛醇(1006.58g，2764.5mmol)，和在MIBK(47.84g)中的氯化铁(0.24g)。将反应混合物加热至90℃，持续2小时。加入油醇(91.91g，291.00mmol)。将反应混合物保持在90℃，再持续2小时。加入乙醇酸(210.24g，2764.5mmol)。然后将反应混合物保持在90℃，持续18小时。加入水(6.49g)用于交联。该混合物保持在90℃下1小时，然后冷却至70℃。经由加料漏斗，在30分钟内加入在水(15772.29g)中的十二烷基苯磺酸钠(73.88g)。将混合物保持在70℃，持续18小时。加入浓NH4OH水溶液(28％，168.14g，2764.50mmol NH3)。在pH 7下形成白色浆液，然后将内容物在70℃下加热搅拌30分钟。经由奶匀化器将混合物匀化。减压蒸发溶剂，获得白色浆液的聚氨酯分散体，，其具有15.6重量％的固体。将计算量的这种分散体(350ppm F)加到外用测试漆的样品中，并且按照所述测试方法评估刮涂板。
比较例A
带有回流冷凝器、温度探头、磁力搅拌棒、和N2气氛的圆底烧瓶装入在MIBK(22mL)中的异佛乐酮二异氰酸酯(5g，22.5mmo1)。然后加入1H，1H，2H，2H-全氟辛-1-醇(4.3g，11.8mmol)和在MIBK(24mL)中的聚(乙二醇)一甲基醚(Mn约750，8.85g，11.8mmol)。混合物加热至80℃，并且装入二月桂酸二丁基锡(0.01g)。加热混合物20小时。然后加入在MIBK(22mL)中的二羟基甲基丙酸(3.02g，22.5mmol)，并且将混合物在80℃下加热，持续12小时。聚氨酯溶液然后用NH4OH中和，并且减压去除有机物。发现分散体为27重量％的固体。
比较例B
将不含添加剂的外用测试漆的样品施加到刮涂板，并且按照所述的测试方法进行评估。
表1：油接触角和耐积垢性
*值越高，表示接触角性能越好。
**值越低，表示DPR性能越好。
数据表示与其中不存在添加剂的比较例B相比，可交联的聚氨酯显示出优异的初始DPR和油接触角。此外，与其中不存在烯属可交联基团的比较例A相比，实施例1-3的可交联的聚氨酯在水洗和WOM时显示出优异的油接触角保持性能。与在WOM后的比较例B相比，所有实施例也显示出良好的DPR。
Claims (15)
1.一种可交联化合物，所述可交联化合物具有至少一个烯键式不饱和官能团，所述可交联化合物包括试剂的反应产物，所述试剂包括：
(a)具有至少2个异氰酸酯基团的至少一种异氰酸酯化合物、或所述化合物的混合物；
(b)至少一种式(I)的全氟烷基单醇、或所述全氟烷基单醇的混合物；
Rf-Qv-OH (I)
其中
Rf为2至20个碳原子的直链或支链的全氟烷基基团，任选地间杂有一个或多个醚氧-O-、- CH2- 、- CFH- 、或它们的组合；
Q为直链、支链或环状结构的亚烷基、亚芳基、亚芳烷基、磺酰基、砜基或亚砜基、亚磺酰氨基、亚碳酰氨基、羰基氧基、亚尿烷基、1,3-亚脲基、或这样的连接基团的组合；并且
v为0或1；
(c)至少一种异氰酸酯反应性化合物，所述化合物具有一个选自OH、NH2、或SH的异氰酸酯反应性官能团并且具有至少一个烯键式不饱和基团；
(d)至少一种异氰酸酯反应性化合物，所述化合物具有至少一个末端羧酸和一个选自OH、NH2、或SH的异氰酸酯反应性官能团；以及
(e)任选地，至少一种附加的异氰酸酯反应性化合物，所述化合物选自水、烷氧基化二醇、或羟基官能的光引发剂化合物；
前提条件是如果所述异氰酸酯化合物(a)具有2个异氰酸酯基团，则水作为附加的异氰酸酯反应性化合物(e)存在。
2.根据权利要求1所述的可交联化合物，其中Rf为C2至C6全氟烷基基团，v为1，并且Q为C1至C6亚烷基基团。
3.根据权利要求1所述的可交联化合物，其中所述至少一种异氰酸酯反应性化合物(c)选自羟烷基乙烯基化合物、含有2至30个碳的烷基链并且具有1至15个烯属单元的直链或支链的醇、烯丙基或甲基烯丙基聚醚醇、氨基烷基乙烯基化合物、丙烯酸类或甲基丙烯酸类烷基醇、(甲基)丙烯酸类聚醚醇、或(甲基)丙烯酸类胺。
4.根据权利要求1所述的可交联化合物，其中所述至少一种异氰酸酯反应性化合物(d)选自羟基乙酸、羟基丙酸、或聚乳酸。
5.根据权利要求1所述的可交联化合物，其中所述至少一种异氰酸酯化合物选自式(IIa)、(IIb)、(IIc)、(IId)、和(IIe)的化合物：
6.根据权利要求1所述的可交联化合物，其中化合物(e)是存在的。
7.一种组合物，所述组合物包含
(a)涂料基料，所述涂料基料选自水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料；和
(b)可交联添加剂，其中所述可交联添加剂为根据权利要求1所述的可交联化合物；
其中所述组合物包含基于所述(a)和(b)的总重量计95重量％至99.98重量％的量的(a)和0.02重量％至5重量％的量的(b)。
8.根据权利要求7所述的组合物，其中Rf为C2至C6全氟烷基基团；v为1，并且Q为C1至C6亚烷基基团。
9.根据权利要求7所述的组合物，其中所述至少一种异氰酸酯反应性化合物(c)选自羟烷基乙烯基化合物、含有2至30个碳的烷基链并且具有1至15个烯属单元的直链或支链的醇、烯丙基或甲基烯丙基聚醚醇、氨基烷基乙烯基化合物、丙烯酸类或甲基丙烯酸类烷基醇、(甲基)丙烯酸类聚醚醇、或(甲基)丙烯酸类胺。
10.根据权利要求7所述的组合物，其中所述至少一种异氰酸酯反应性化合物(d)选自羟基乙酸、羟基丙酸、或聚乳酸。
11.根据权利要求7所述的组合物，其中所述涂料基料为选自含水丙烯酸类乳胶漆的水分散的涂料。
12.根据权利要求7所述的组合物，其中所述涂料基料包含选自下列的添加剂：TiO2、粘土、石棉、碳酸钙、氧化锌、氧化铬、硫酸钡、氧化铁、氧化锡、硫酸钙、滑石、云母、硅石、白云石、硫化锌、氧化锑、二氧化锆、二氧化硅、硫化镉、硒化镉、铬酸铅、铬酸锌、钛酸镍、硅藻土、玻璃纤维、玻璃粉、玻璃球、蓝色颜料、红色颜料、黄色颜料、橙色颜料、棕色颜料、或绿色颜料。
13.一种用于形成具有改善耐积垢性的涂层的方法，所述方法包括
(i)使选自水分散的涂料、环氧聚合物涂料、醇酸涂料、I型聚氨酯涂料、或不饱和聚酯涂料的涂料基料与具有至少一个烯键式不饱和官能团的可交联化合物接触以形成涂料混合物；
(ii)将所述涂料混合物施加到基底以形成涂层；
(iii)允许所述可交联化合物迁移到所述涂层表面以形成可交联的表面涂层，以及
(iv)随后使所述可交联的表面涂层的所述烯键式不饱和基团一起反应；
其中
所述涂料混合物包含基于所述涂料基料和所述可交联化合物的总重量计95重量％至99.98重量％的量的所述涂料基料和0.02重量％至5重量％的量的所述可交联化合物；
具有至少一个烯键式不饱和官能团的所述可交联化合物包括试剂的反应产物，所述试剂包括：
(a)具有至少2个异氰酸酯基团的至少一种异氰酸酯化合物、或所述化合物的混合物；
(b)至少一种式(I)的全氟烷基单醇、或所述全氟烷基单醇的混合物；
Rf-Qv-OH (I)
其中
Rf为2至20个碳原子的直链或支链的全氟烷基基团，任选地间杂有一个或多个醚氧-O-、- CH2- 、- CFH- 、或它们的组合；
Q为直链、支链或环状结构的亚烷基、亚芳基、亚芳烷基、磺酰基、砜基或亚砜基、亚磺酰氨基、亚碳酰氨基、羰基氧基、亚尿烷基、1,3-亚脲基、或这样的连接基团的组合；并且
v为0或1；
(c)至少一种异氰酸酯反应性化合物，所述化合物具有一个选自OH、NH2、或SH的异氰酸酯反应性官能团并且具有至少一个烯键式不饱和基团；
(d)至少一种异氰酸酯反应性化合物，所述化合物具有至少一个末端羧酸和一个选自OH、NH2、或SH的异氰酸酯反应性官能团；以及
(e)任选地，至少一种附加的异氰酸酯反应性化合物，所述化合物选自水、烷氧基化二醇、或羟基官能的光引发剂化合物；
前提条件是如果所述异氰酸酯化合物(a)具有2个异氰酸酯基团，则水作为附加的异氰酸酯反应性化合物(e)存在。
14.一种涂覆的基底，所述涂覆的基底通过根据权利要求13所述的方法制得。
15.根据权利要求14所述的涂覆的基底，其中所述基底选自木材、金属、墙板、砖石、混凝土、纤维板和纸材。
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| PCT/US2016/029664 WO2016176389A1 (en) | 2015-04-30 | 2016-04-28 | Crosslinkable fluorinated urethane additives for durable exterior coatings |
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| US11261288B2 (en) | 2017-08-22 | 2022-03-01 | Arkema France | Allyl functional urethane oligomers and related compositions for coatings and adhesives |
| CN112048226B (zh) * | 2020-09-13 | 2021-09-03 | 上海普信高分子材料有限公司 | 一种耐酸碱氟硅丙烯酸树脂涂层及其制备方法 |
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| EP3289022B1 (en) | 2020-10-28 |
| CN107810216A (zh) | 2018-03-16 |
| EP3289022A1 (en) | 2018-03-07 |
| US20200377742A1 (en) | 2020-12-03 |
| US10781283B2 (en) | 2020-09-22 |
| WO2016176389A1 (en) | 2016-11-03 |
| US10899939B2 (en) | 2021-01-26 |
| HK1252356A1 (zh) | 2019-05-24 |
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