CN112250816A - 一种侧链含氟降解聚氨酯树脂的制备方法 - Google Patents
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Abstract
本发明提供了一种侧链含氟降解聚氨酯树脂的制备方法,利用异氟尔酮二异氰酸酯在催化剂二月桂酸二丁基锡下两个‑NCO基团的反应活性不同,将聚乙二醇链段和疏水性含氟聚合物链段同时接枝到丙烯酸树脂侧链得到含氟降解聚氨酯树脂。由于聚乙二醇链段的加入能够改善树脂的降解性能,利用含氟聚合物链段的低表面能性质以及更易在表面聚集的性质可以更好的抑制蛋白质分子以及海洋污损生物的附着,以达到更好的防污效果。
Description
技术领域
本发明属于化工材料技术领域,具体地说,本发明涉及一种防污涂料用侧链含氟降解聚氨酯树脂的制备方法。
背景技术
船舶运输作为一种拥有较低成本且利用海洋运输而不受陆地不同地形的限制的运输方式,在运输业中占据了很大的比重。但是海洋中存在的海洋污损生物不仅会增大航行阻力、增加油耗,还会使船舶及海洋设备腐蚀加剧,导致设备发生故障。目前主要的防污方式便是在船舶表面涂覆防污涂料。市场中大部分使用的防污涂料为无锡自抛光型防污涂料,防污机理是通过加入氧化亚铜作为防污剂,涂层在海水中逐渐分解释放出防污剂,进而杀死海洋污损生物。此类防污涂料的缺点在于加入的氧化亚铜会在生物体内富集,破坏海洋的生态环境。随着防污涂料的配方工艺的不断的进步,不断从传统的添加毒料杀死附着生物的方式到无毒、环境友好型防污涂料发展。
丙烯酸系聚合物是良好的成膜物质并且具有良好的物理化学性能,用其作为树脂基体制备的涂料具有着良好的性能,如颜色纯正、有着良好的耐候性能,耐光性、对于酸碱等都有着良好的抗腐蚀性能,并且可以通过对于共聚单体的配方调试可以获得具有不同硬度、强度的漆膜。
本发明通过在丙烯酸树脂侧链接枝上含氟聚合物和聚乙二醇,构成含氟结构的聚氨酯树脂基体,并且聚乙二醇链段的加入以改善聚氨酯树脂的降解性能,利用含氟聚合物链段的低表面张力的性能来抑制蛋白质分子的表面吸附性能,通过物理防污来提高抑制海洋生物的附着的效果,得到防污涂料用侧链含氟降解聚氨酯树脂。
发明内容
本发明的目的在于提供一种防污涂料用侧链含氟降解聚氨酯树脂的制备方法。
为实现上述目的,本发明采用如下技术方案:
一种侧链含氟降解聚氨酯树脂的制备方法,包括如下步骤:
1)将丙烯酸树脂(聚甲基丙烯酸-2-羟乙酯)在二甲苯中溶解分散倒入三口烧瓶内,在冰水浴条件下加入异氟尔酮二异氰酸酯,加入催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;
2)将1H,1H,2H,2H-全氟-1-辛醇在四氢呋喃中分散,在冰水浴条件下加入异氟尔酮二异氰酸酯,加入催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备基团改性的1H,1H,2H,2H-全氟-1-辛醇;
3)将基团改性的丙烯酸树脂加入三口烧瓶中,缓慢滴入聚乙二醇(分子量为200-800),在250r/min的转速下加热至50℃反应2h,再滴入基团改性的1H,1H,2H,2H-全氟-1-辛醇在60℃反应2h,得到侧链含氟降解聚氨酯树脂。
本发明的优点在于:
本发明以侧链包含反应性基团羟基的丙烯酸树脂作为基料,聚乙二醇作为改善降解速率链段,含氟聚合物作为疏水性低表面能链段,利用异氟尔酮二异氰酸酯作为连接剂将两聚合物链段接枝到侧链中以构成含氟结构的聚氨酯树脂。聚乙二醇链段的加入能够改善聚氨酯树脂的降解性能,利用含氟聚合物链段的低表面能性质以及更易在表面聚集的性质可以更好的抑制蛋白质分子以及海洋污损生物的附着,以达到更好的防污效果。
(1)采用异氟尔酮二异氰酸酯进行基团改性
由于异氟尔酮二异氰酸酯中两个异氰酸基团所处的化学环境不同,导致两个异氰酸基团的活性不同。当使用二月桂酸二丁基锡作为催化剂时,反应活性高的-NCO基团先与-OH基团反应生成-NHCOO基团,当其反应完全后,活性低的-NCO基团才开始与-OH基团反应。
(2)构成侧链含氟结构以获得低表面能性质以提高防污能力
在丙烯酸树脂侧链上同时接枝聚乙二醇和含氟聚合物,其制备的防污涂料在基板上附着后,氟原子会分布于涂层表面使涂层具有低表面能、优异的化学稳定性和热稳定性,能够提高抑制海洋污损生物的附着的效果。同时聚乙二醇的加入能够改善聚氨酯的降解性能以提高涂层的防污性能。
附图说明
图1为聚合物薄膜在海水中的失重率, A为侧链接枝含氟聚合物的聚氨酯树脂,B为同时接枝聚乙二醇和含氟聚合物的聚氨酯树脂;
图2为防污涂料用侧链含氟聚氨酯树脂合成路线图;
图3为本发明合成的侧链含氟聚氨酯树脂的红外谱图;
图4为聚合物薄膜表面硅藻附着密度。
具体实施方式
为让本发明的上述特征和优点能更明显易懂,下文特举实施例,作详细说明。本发明的方法如无特殊说明,均为本领域常规方法。
实施例1:将10g聚甲基丙烯酸-2-羟乙酯在二甲苯中溶解分散倒入三口烧瓶内,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.15g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;将17.47g1H,1H,2H,2H-全氟-1-辛醇在四氢呋喃中分散,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.23g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h;称取38.4gPEG800缓慢滴入装有基团改性的丙烯酸树脂的三口烧瓶中,在250r/min的转速下加热至50℃反应2h,再滴入改性后的1H,1H,2H,2H-全氟-1-辛醇加热至60℃反应2h,反应完成后进行提纯、过滤。
图3为本发明合成的侧链含氟聚氨酯树脂的红外谱图;其中,a为基团改性后的丙烯酸树脂,b为接枝上聚乙二醇的丙烯酸树脂,c为同时接枝聚乙二醇和含氟聚合物的丙烯酸树脂。曲线a中3338cm-1为氨基甲酸酯键中的-NH伸缩振动,1538cm-1为-NH的弯曲振动;2266cm-1为-NCO基团的特征吸收峰;1720cm-1为C=O的伸缩振动;1104cm-1为C-O-C的对称伸缩振动。曲线b中3517cm-1为聚乙二醇中-OH的伸缩振动,-NCO基团的特征吸收峰(2266cm-1)消失,说明聚乙二醇中的-OH与-NCO基团反应。曲线c中-NCO基团的特征吸收峰(2266cm-1)未出现,1238cm-1为C-F的伸缩振动强吸收峰,将1259cm-1峰掩盖,证明存在着C-F。
实施例2:将10g聚甲基丙烯酸-2-羟乙酯在二甲苯中溶解分散倒入三口烧瓶内,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.08g(0.25ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;将13.98g 1H,1H,2H,2H-全氟-1-辛醇在四氢呋喃中分散,在冰水浴条件下加入8.53g异氟尔酮二异氰酸酯,加入0.09g(0.25ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h;称取23.04gPEG600缓慢滴入装有基团改性的丙烯酸树脂的三口烧瓶中,在250r/min的转速下加热至50℃反应2h,再滴入改性后的1H,1H,2H,2H-全氟-1-辛醇加热至60℃反应2h,反应完成后进行提纯、过滤。
实施例3:将10g聚甲基丙烯酸-2-羟乙酯在二甲苯中溶解分散倒入三口烧瓶内,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.15g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;将13.98g1H,1H,2H,2H-全氟-1-辛醇在四氢呋喃中分散,在冰水浴条件下加入8.53g异氟尔酮二异氰酸酯,加入0.18g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h;称取19.2gPEG400缓慢滴入装有基团改性的丙烯酸树脂的三口烧瓶中,在250r/min的转速下加热至50℃反应2h,再滴入改性后的1H,1H,2H,2H-全氟-1-辛醇加热至60℃反应2h,反应完成后进行提纯、过滤。
实施例4:将10g聚甲基丙烯酸-2-羟乙酯在二甲苯中分散倒入三口烧瓶内,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.15g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;将17.47g1H,1H,2H,2H-全氟-1-辛醇在四氢呋喃中分散,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.23g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h;称取7.68g PEG200缓慢滴入装有基团改性的丙烯酸树脂的三口烧瓶中,在250r/min的转速下加热至50℃反应2h,再滴入改性后的1H,1H,2H,2H-全氟-1-辛醇加热至60℃反应2h,反应完成后进行提纯、过滤。
对比例:
将10g聚甲基丙烯酸-2-羟乙酯在二甲苯中溶解分散倒入三口烧瓶内,在冰水浴条件下加入10.66g异氟尔酮二异氰酸酯,加入0.15g(0.5ωt%)催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;称取17.47g 1H,1H,2H,2H-全氟-1-辛醇缓慢滴入装有基团改性的丙烯酸树脂的三口烧瓶中,在250r/min的转速下加热至50℃反应2h,得到侧链接枝含氟聚合物的聚氨酯树脂。
降解实验:
将聚合物在载玻片中制成聚合物薄膜称量薄膜的质量,将其放入海水中间隔一定时间后取出,进行干燥称取重量。防污涂料用侧链含氟聚氨酯树脂的降解速率数据如图1所示:
图1中A为侧链接枝含氟聚合物的聚氨酯树脂(对比例)在海水中的失重率,B为实施例1中同时接枝聚乙二醇和含氟聚合物的聚氨酯树脂在海水中的失重率。从图中可以看出在侧链只有含氟聚合物的时候由于含氟聚合物链段的疏水性,薄膜的降解速率较慢。在接枝上聚乙二醇链段后由于其亲水性容易水解,降解速率会明显大于侧链仅有含氟聚合物链段聚氨酯树脂。因此可以通过加入聚乙二醇链段来调节改善聚氨酯树脂的降解性能。
防污实验:
取用天然海水,经滤膜过滤后放入高压灭菌锅进行灭菌处理。然后取200ml灭菌海水,加入藻类专用的营养液,加入舟型硅藻液,温度设置为25℃,光照3级。每隔24h拿出放置在摇床上摇动30min,大约5-7天达到生长指数期。将树脂置于载玻片表面,待其固化,将载玻片移入培养皿中,最后将硅藻培养液滴入培养皿中。在25℃培养箱中培养一周,取出载玻片,用少量清水缓慢冲洗薄膜表面,然后采用倒置显微镜观察薄膜表面硅藻附着情况。其附着密度如图4所示:
从图中可以看出经过一周后,在各聚合物薄膜中,对比例中的硅藻附着密度相比于实施例中的硅藻密度有大幅度的增加,说明在侧链只接枝含氟聚合物的聚氨酯树脂抑制硅藻附着的能力不如同时接枝上聚乙二醇和含氟聚合物的降解型聚氨酯树脂。同时从实施例硅藻附着密度对比中可以看出,随着聚乙二醇分子量的增加,硅藻的附着呈现出下降的趋势。
以上所述仅为本发明的较佳实施例,凡依本发明申请专利范围所做的均等变化与修饰,皆应属本发明的涵盖范围。
Claims (2)
1.一种侧链含氟降解聚氨酯树脂的制备方法,其特征在于,包括如下步骤:
(1)将聚甲基丙烯酸-2-羟乙酯在二甲苯中溶解分散倒入三口烧瓶内,在冰水浴条件下加入异氟尔酮二异氰酸酯,加入催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备出基团改性的丙烯酸树脂;
(2)将1H,1H,2H,2H-全氟-1-辛醇在四氢呋喃中分散,在冰水浴条件下加入异氟尔酮二异氰酸酯,加入催化剂二月桂酸二丁基锡,在250r/min转速下逐渐升温至40℃反应2h制备基团改性的1H,1H,2H,2H-全氟-1-辛醇;
(3)将基团改性的丙烯酸树脂加入三口烧瓶中,缓慢滴入聚乙二醇,在250r/min的转速下加热至50℃反应2h,再滴入基团改性的1H,1H,2H,2H-全氟-1-辛醇在60℃反应2h,得到侧链含氟降解聚氨酯树脂。
2.根据权利要求1所述的制备方法,其特征在于,聚乙二醇分子量为200-800。
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