CN107974191A - 一种萘基改性化合物和uv型阴极电泳涂料及其制备与应用 - Google Patents
一种萘基改性化合物和uv型阴极电泳涂料及其制备与应用 Download PDFInfo
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- CN107974191A CN107974191A CN201711146359.XA CN201711146359A CN107974191A CN 107974191 A CN107974191 A CN 107974191A CN 201711146359 A CN201711146359 A CN 201711146359A CN 107974191 A CN107974191 A CN 107974191A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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Abstract
本发明属于电泳涂料的技术领域,公开了一种萘基改性化合物和UV型阴极电泳涂料及其制备与应用。所述萘基改性化合物的结构式为式I。所述UV型阴极电泳涂料由以下按重量份的组分组成:甲基丙烯酸二甲氨基乙酯10~25份、甲基丙烯酸甲酯15~30份、丙烯酸羟乙酯4~20份、丙烯酸丁酯15~30份、苯乙烯5~20份、二异氰酸酯5~20份、催化剂0.2~1份、阻聚剂1~2份、自由基引发剂1~10份、分散剂2~8份、光引发剂2~8份、萘基改性化合物5~30份、中和剂3~10份、有机溶剂102~210份、水100~1500份。所述UV型阴极电泳涂料具有较好的耐热性、硬度以及光泽度;用于制备电泳制品。
Description
技术领域
本发明属于电泳涂料的技术领域,具体涉及一种萘基改性化合物和UV型阴极电泳涂料及其制备方法与应用。
背景技术
电泳涂料是一种环保水性涂料,电泳涂料经过数代发展和演变,目前市场占主流的是阴极电泳涂料。阴极电泳涂料涂膜固化方式主要为热固化,存在固化温度高的缺点,约为140~180℃,其次固化时间较长,约为30min以上。因此导致许多材料因温度的影响较难进行电泳涂装,同时效率低,能耗大,成本高。为解决这类问题的常常采用是降低涂料涂装时的固化成膜的温度。紫外光(UV)固化是上个世纪60年代出现的一种新型的表面处理技术,通过紫外光引发具有化学活性的液态材料快速聚合交联,立即固化成固态材料。
紫外光固化阴极电泳涂装不需要很高的固化温度,满足产品在电泳涂装时,涂装基材受温度影响的问题,同时一定程度上克服了电泳涂料热固化的缺点,将紫外光固化技术应用到水性涂料,避免了传统的紫外光固化涂料使用活性稀释剂用来调节体系的粘度和流变性,从而促进漆膜的成膜和固化,有很好的发展应用前景。
紫外光固化阴极电泳涂料在应用中也存在一些问题,如可供选择的光引发剂种类不多,漆膜的闪蒸过程对UV固化阴极电泳涂料的性能及其固化速率有着极为重要的影响,同时也存在漆膜硬度和耐热性差问题。
目前常见的紫外光固化阴极电泳涂料存在耐热性差,硬度低。因此非常有必要提供一种具有UV耐热性兼有硬度高的紫外光固化阴极电泳涂料。
发明内容
为了解决现有技术的缺点和不足之处,本发明的首要目的在于提供一种刚性结构的耐热单体即萘基改性化合物及其制备方法。
本发明的另一目的在于提供一种利用上述萘基改性化合物制备的UV型阴极电泳涂料及其制备方法。本发明通过采用萘基改性化合物,解决了UV型阴极电泳涂料耐热性差、硬度低的技术问题。
本发明的再一目的在于提供上述UV型阴极电泳涂料的应用。所述电泳涂料用于制备电泳制品。
本发明的目的通过以下技术方案实现:
一种萘基改性化合物,其结构式为式I
所述萘基改性化合物的制备方法为以有机溶剂为反应介质,以2-萘甲醛和丙烯酸甲酯为反应原料,在催化剂的作用下反应原料进行反应,纯化,得到萘基改性化合物。
所述2-萘甲醛与丙烯酸甲酯的摩尔比为(0.1~0.4)mol:(0.2~0.6)mol。
所述2-萘甲醛与催化剂的用量比为(0.1~0.4)mol:(0.1~0.5)mol;所述2-萘甲醛与有机溶剂的用量比为(0.1~0.4)mol:(50~200)ml。
所述催化剂为三乙胺、三乙烯二胺、四丁基硫酸氢胺、四丁基溴化胺、三乙基苄基氯化胺、4-二甲氨基吡啶中的一种以上;所述有机溶剂为四氢呋喃、乙酸乙酯、甲醇、二甲基亚砜、二甲基甲酰胺中的一种以上。
所述反应的温度为常温,所述反应通过薄层色谱法TLC监控反应是否完成。
所述纯化是指将反应后的产物用去离子水溶解,随后用萃取液萃取,有机相采用干燥剂干燥,过滤,旋蒸,硅胶柱层析,旋蒸,得到萘基改性化合物。
所述萃取液为四氯化碳、乙醇(酒精)、乙酸乙酯中的一种以上;所述干燥剂为无水硫酸镁、无水硫酸钠、无水碳酸钠中的一种以上。
所述旋蒸的温度为30~60℃;干燥剂干燥的时间为6~10h。
所述去离子水用量为50~300ml、萃取液用量为10~50ml、干燥剂用量为5~10g。
一种利用上述萘基改性化合物制备的UV型阴极电泳涂料。
一种利用上述萘基改性化合物制备的UV型阴极电泳涂料,由以下按重量份的组分组成:甲基丙烯酸二甲氨基乙酯(DMAEMA)10~25份、甲基丙烯酸甲酯(MMA)15~30份、丙烯酸羟乙酯(HEA)4~20份、丙烯酸丁酯(BA)15~30份、苯乙烯(St)5~20份、二异氰酸酯5~20份、催化剂0.2~1份、阻聚剂1~2份、自由基引发剂1~10份、分散剂2~8份、光引发剂2~8份、萘基改性化合物5~30份、中和剂3~10份、有机溶剂102~210份、水100~1500份。
所述二异氰酸酯为异佛尔酮二异氰酸酯(IPDI)。
所述催化剂为三乙胺、二月桂酸二丁基锡、三乙烯二胺、四丁基硫酸氢胺、四丁基溴化胺、三乙基苄基氯化胺、4-二甲氨基吡啶中的一种以上。
所述阻聚剂为对苯二酚、对苯醌、2,6-二叔丁基对甲苯酚、β-苯基萘胺、对叔丁基邻苯二酚中的一种以上。
所述自由基引发剂为偶氮二异丁腈、偶氮二异丁酸二甲酯、过氧化苯甲酰中的一种以上。
所述分散剂为乙二醇单丁醚、丙烯乙二醇单丁醚、丙二醇单丙醚、丙二醇单丁醚中的一种以上。
所述光引发剂为1-羟基环己基苯基甲酮、2-羟基-2-甲基-1-苯基丙酮、2,4,6-三甲基苯甲酰基-二苯基氧化膦、2-羟基-2-甲基-1-[4-(2-羟基乙氧基)苯基]-1-丙酮中的一种以上。
所述中和剂为乳酸、冰醋酸、硝酸、二羟基甲基丙酸中的一种以上。
所述有机溶剂为丙二醇甲醚醋酸酯、乙酸乙酯、甲醇、二甲基亚砜、甲基异丁基酮中的一种以上。
所述UV型阴极电泳涂料的制备方法,包括以下步骤:
(1)将甲基丙烯酸二甲氨基乙酯(DMAEMA)10~25份、甲基丙烯酸甲酯(MMA)15~30份、丙烯酸羟乙酯(HEA)2~10份、丙烯酸丁酯(BA)15~30份、苯乙烯(St)5~20份、自由基引发剂1~10份和有机溶剂50~100份混合均匀,得到混合单体溶液;在搅拌的条件下(搅拌转速为120~200r/min),于70℃~90℃,向50~100份有机溶剂中,滴加混合单体溶液,滴加完毕后保温4~6h,减压蒸馏至固含量为50wt%~70wt%,得到产物A;
(2)将二异氰酸酯5~20份和阻聚剂0.5~1份混合均匀,然后在40~70℃下,滴加由丙烯酸羟乙酯(HEA)2~10份和催化剂0.1~0.5份混合而成的混合物,滴加完后,持续反应,当反应体系中-NCO的含量达到半封闭后的理论值的含量时,终止反应,得到产物B;
(3)将催化剂0.1~0.5份、阻聚剂0.5~1份溶于2~10份有机溶剂中,得到催化剂和阻聚剂的混合溶液;将催化剂和阻聚剂的混合溶液与步骤(2)的产物B混合均匀,得到混合物;在搅拌的条件下(搅拌转速为100~150r/min),于40℃~70℃,向步骤(1)的产物A中滴加混合物,滴加完毕,保温3~4h,得到树脂产物;
(4)于40℃~70℃,向步骤(3)的树脂产物加入中和剂3~10份,搅拌均匀,降至室温,加入分散剂2~8份、光引发剂2~8份和萘基改性化合物5~30份,分散均匀,逐步加入100~1500份水使得固含量为10~20%,高速乳化分散,熟化,得到UV型阴极电泳涂料。
步骤(4)中所述高速乳化分散的条件为3000~6000r/min转速下分散20~60min,熟化的条件为以150~250r/min熟化24~48h。
步骤(4)中所述搅拌均匀是指以120~200r/min的速度搅拌20~60min;所述分散均匀是指以180~250r/min转速搅拌5~10min。
步骤(1)中所述减压蒸馏的温度为40℃~70℃;减压蒸馏前需冷却;所述滴加需在2-3h内滴加完毕;
步骤(2)的反应体系中-NCO的含量用二正丁胺法滴定测定;
步骤(2)中所述滴加需在1~2h内滴加完毕;
步骤(3)中所述滴加需1~2h内滴加完毕。
所述UV型阴极电泳涂料用于制备电泳制品。
所述电泳制品包括基底极板以及沉积在基底极板表面的UV型阴极电泳涂料沉积层。所述基底极板是磷化处理过的铁板。
所述电泳制品的具体制备方法为:以UV型阴极电泳涂料为工作液,以铝合金板作为阳极,以基底极板为阴极,进行电泳处理,清洗,干燥,UV灯照射,得到电泳制品。所述阴极和阳极的间距为8~15cm;所述电泳的电源电压100~150V,电泳的时间为60~180s;所述清洗是指用去离子水清洗阴极板表面浮液,所述干燥为于60~100℃干燥2~3min,所述UV灯照射的条件为于1000W~2000W的UV灯下照射10~60s。
所述电泳沉积层厚度为10~15μm。
本发明的有益效果是:本发明的萘基改性化合物具有比苯环更加稳定刚性结构,同时在电泳涂料制备的过程中链封端的异酸酸酯羟基与异氰酸根反应,会进一步提高分子内的交联程度,这将极大提升UV阴极电泳涂料的耐热性、硬度以及光泽度。因此改性后UV阴极电泳涂料具有广阔的应用前景。
附图说明
图1为实施例1中萘基改性化合物的核磁谱图。
具体实施方式
下面结合附图和具体实施例对本发明作进一步详细的描述,但本发明不限于此。薄层色谱法TLC是将适宜的固定相涂布于玻璃板上,成一均匀薄层;待点样、展开后,根据比移值(Rf)与原料按同法所得的色谱图的比移值(Rf)作对比,来监控反应是否完成;当出现与原料点相比极性较大的点时,反应结束。
所述TLC洗脱液是指分别为乙酸乙酯和正己烷。
实施例1
(1)将2-萘甲醛(0.1mol)、丙烯酸甲酯(0.2mol)、4-二甲氨基吡啶(0.15mol)以及有机溶剂四氢呋喃(50ml)混合均匀,在常温下搅拌24h,通过薄层色谱法TLC监控反应是否完成,反应结束后,用去离子水(50ml)水洗溶解,用乙酸乙酯(10ml)萃取,将有机相加入无水硫酸镁(5g)干燥6h,过滤,30℃下减压旋蒸出溶剂,硅胶柱层析,30℃旋蒸,得到萘基改性化合物;
(2)将甲基丙烯酸二甲氨基乙酯(DMAEMA)10份、甲基丙烯酸甲酯(MMA)15份、丙烯酸羟乙酯(HEA)4份、丙烯酸丁酯(BA)15份、苯乙烯(St)5份、偶氮二异丁酸二甲酯2份和有机溶剂丙二醇甲醚醋酸酯50份搅拌均匀备用;将配有搅拌装置,球形冷凝管以及温度计的500mL四口烧瓶置于温度75℃水浴中,向其加入有机溶剂丙二醇甲醚醋酸酯50份搅拌混合均匀,得到混合单体溶液;在搅拌的条件下(搅拌转速为120r/min),于75℃,向50份有机溶剂丙二醇甲醚醋酸酯中,滴加混合单体溶液,控制蠕动泵滴速10rpm,在2h内滴加完毕,保温4h,冷却出料,40℃减压蒸馏至固含量为50wt%左右,得到产物A;
(3)将异佛尔酮二异氰酸酯(IPDI)5份和对苯二酚0.5份混合均匀,然后在搅拌和40℃条件下,滴加由丙烯酸羟乙酯(HEA)2份和三乙胺0.1份混合而成的混合物,通过蠕动泵,控制滴速4rpm,在2h内滴加完毕;滴加完毕后5min后用二正丁胺法滴定法(方法参考国标GBT 18446-2009)测定反应体系中-NCO含量,直至-NCO的含量达到半封闭后的理论值(-NCO,9.18%)的含量,终止反应,得到产物B;
(4)将三乙胺0.1份、对苯二酚0.5份溶于2份有机溶剂丙二醇甲醚醋酸酯中,得到催化剂和阻聚剂的混合溶液;将催化剂和阻聚剂的混合溶液与步骤(3)的产物B混合均匀,得到混合物;在搅拌的条件下(搅拌转速为100r/min),于40℃,向步骤(2)的产物A中滴加混合物,采用蠕动泵滴加,控制滴速5rpm,2h内滴加完毕,保温3h(使用傅立叶红外光谱仪表征分析,确保异氰酸根与羟基反应完全),得到树脂产物;
(5)于40℃,向步骤(4)的树脂产物加入乳酸3份,以120r/min的搅拌速度搅拌20min;然后降至室温,加入乙二醇单丁醚3份、1-羟基环己基苯基甲酮3份和萘基改性化合物5份,以180r/min转速搅拌10min,从而分散均匀;分三次逐渐加入去离子水至固含量降低为20%(质量百分数),用高速分散机进行乳化分散(3000r/min转速下分散60min),以150r/min熟化48h,得到UV型阴极电泳涂料即UV光固化改性丙烯酸水性阴极电泳涂料工作液;
(6)以上述UV型阴极电泳涂料为工作液(阴极电泳工作液),将阴极电泳工作液加入电泳槽中,以150r/min转速进行搅拌;用洁净的铝合金板作为阳极,用乙醇和丙酮清洗后的5×7.5cm磷化板(磷化处理的铁板)作为阴极,两者同等程度地浸入工作液中,调整板间距为8cm;调节电源电压100V后,电泳180s后断开电源;使用去离子水清洗阴极板表面浮液,沥干后置于鼓风干燥箱在70℃干燥3min,去除表面水分;待极板降温后,将其放置于1000W的UV灯下照射20s,获得表面光滑平整的电泳制品。
实施例1中萘基改性化合物的核磁谱图如图1所示。
所述电泳沉积层厚度为10μm,铅笔硬度为6H,耐热性为100℃保持性能不变,光泽度为75,耐丁酮擦拭次数为100,附着力为0级。
实施例2
(1)将2-萘甲醛(0.2mol)、丙烯酸甲酯(0.3mol)、三乙烯二胺(0.2mol)以及有机溶剂乙酸乙酯(100ml)混合均匀,在常温下搅拌30h,通过薄层色谱法TLC监控反应是否完成,反应结束后,用去离子水(100ml)水洗溶解,用乙酸乙酯(30ml)萃取,将有机相加入无水硫酸钠(6g)干燥8h,过滤,40℃下减压旋蒸出溶剂,硅胶柱层析,40℃旋蒸,得到萘基改性化合物;
(2)将甲基丙烯酸二甲氨基乙酯(DMAEMA)15份、甲基丙烯酸甲酯(MMA)20份、丙烯酸羟乙酯(HEA)6份、丙烯酸丁酯(BA)20份、苯乙烯(St)8份、偶氮二异丁腈4份和有乙酸乙酯80份搅拌混合均匀,得到混合单体溶液;在搅拌的条件下(搅拌转速为175r/min),于80℃,向80份有机溶剂乙酸乙酯中,滴加混合单体溶液,控制蠕动泵滴速12rpm,在2.5h内滴加完毕,保温5h,冷却出料,50℃减压蒸馏至固含量为60wt%左右,得到产物A;
(3)将异佛尔酮二异氰酸酯(IPDI)10份和2,6-二叔丁基对甲苯酚0.7份混合均匀,然后在搅拌和50℃条件下,滴加由丙烯酸羟乙酯(HEA)5份和二月桂酸二丁基锡0.3份混合而成的混合物,通过蠕动泵,控制滴速6rpm,在1.5h内滴加完毕;滴加完毕后10min后用二正丁胺法滴定法(方法参考国标GBT18446-2009)测定反应体系中-NCO含量,直至-NCO的含量达到半封闭后的理论值(-NCO,9.18%)的含量,终止反应,得到产物B;
(4)将二月桂酸二丁基锡0.3份、2,6-二叔丁基对甲苯酚0.6份溶于5份有机溶剂乙酸乙酯中,得到催化剂和阻聚剂的混合溶液;将催化剂和阻聚剂的混合溶液与步骤(3)的产物B混合均匀,得到混合物;在搅拌的条件下(搅拌转速为120r/min),于60℃,向步骤(2)的产物A中滴加混合物,采用蠕动泵滴加,控制滴速6rpm,1.5h内滴加完毕,保温4h(使用傅立叶红外光谱仪表征分析,确保异氰酸根与羟基反应完全),得到树脂产物;
(5)于50℃,向步骤(4)的树脂产物加入冰醋酸5份,以150r/min的搅拌速度搅拌30min;然后降至室温,加入乙二醇单丁醚4份、2-羟基-2-甲基-1-苯基丙酮4份和萘基改性化合物10份,以200r/min转速搅拌8min,分散均匀;分三次逐渐加入去离子水至固含量降低为15%,用高速分散机进行乳化分散(4000r/min转速下分散50min),以200r/min熟化40h,得到UV型阴极电泳涂料即UV光固化改性丙烯酸水性阴极电泳涂料工作液;
(6)以上述UV型阴极电泳涂料为工作液(阴极电泳工作液),将阴极电泳工作液加入电泳槽中,以180r/min转速进行搅拌;用洁净的铝合金板作为阳极,用乙醇和丙酮清洗后的5×7.5cm磷化板(磷化处理的铁板)作为阴极,两者同等程度地浸入工作液中,调整板间距为10cm;调节电源电压120V后,电泳100s后断开电源;使用去离子水清洗阴极板表面浮液,沥干后置于鼓风干燥箱在80℃干燥3min,去除表面水分;待极板降温后,将其放置于1000W的UV灯下照射30s,获得表面光滑平整的电泳制品。
所述电泳沉积层厚度为12μm。铅笔硬度为6H,耐热性为120℃保持性能不变,光泽度为90,耐丁酮擦拭次数为300,附着力为0级。
实施例3
(1)将2-萘甲醛(0.3mol)、丙烯酸甲酯(0.4mol)、四丁基硫酸氢胺(0.3mol)以及有机溶剂甲醇(150ml)混合均匀,在常温下搅拌48h,通过薄层色谱法TLC监控反应是否完成,反应结束后,加入去离子水(200ml)水洗溶解,随后用乙酸乙酯(40ml)萃取,将有机相加入无水硫酸钠(8g)干燥9h后过滤,50℃下减压旋蒸出溶剂,硅胶柱层析,50℃旋蒸,得到萘基改性化合物;
(2)将甲基丙烯酸二甲氨基乙酯(DMAEMA)20份、甲基丙烯酸甲酯(MMA)25份、丙烯酸羟乙酯(HEA)8份、丙烯酸丁酯(BA)25份、苯乙烯(St)10份、偶氮二异丁腈5份和有机溶剂甲醇90份搅拌混合均匀,得到混合单体溶液;在搅拌的条件下(搅拌转速为180r/min),于85℃,向90份有机溶剂甲醇中,滴加混合单体溶液,控制蠕动泵滴速14rpm,在2.5h内滴加完毕,保温5h,冷却后出料,65℃减压蒸馏到固含量为65%,得到产物A;
(3)将异佛尔酮二异氰酸酯(IPDI)15份和对苯醌0.8份混合均匀,然后在搅拌和60℃条件下,滴加由丙烯酸羟乙酯(HEA)8份和四丁基硫酸氢胺0.4份混合而成的混合物,通过蠕动泵,控制滴速8rpm,在1h内滴加完毕;滴加完毕后15min后用二正丁胺法滴定法(方法参考国标GBT 18446-2009)测定反应体系中-NCO含量,直至-NCO的含量达到半封闭后的理论值(-NCO,9.18%)的含量,终止反应,得到产物B;
(4)将四丁基硫酸氢胺0.4份、对苯醌0.8份溶于8份有机溶剂甲醇中,得到催化剂和阻聚剂的混合溶液;将催化剂和阻聚剂的混合溶液与步骤(3)的产物B混合均匀,得到混合物;在搅拌的条件下(搅拌转速为140r/min),于50℃,向步骤(2)的产物A中滴加混合物,采用蠕动泵滴加,控制滴速7rpm,1.2h内滴加完毕,保温3h(使用傅立叶红外光谱仪表征分析,确保异氰酸根与羟基反应完全),得到树脂产物;
(5)于60℃,向步骤(4)的树脂产物加入硝酸8份,以180r/min的搅拌速度搅拌50min;然后降至室温,加入丙烯乙二醇单丁醚6份、2,4,6-三甲基苯甲酰基-二苯基氧化膦6份和萘基改性化合物20份,以220r/min搅拌6min,使其分散均匀;分三次逐渐加入去离子水至固含量降低为10%,用高速分散机进行乳化分散(5000r/min转速下分散30min),以180r/min熟化30h,得到UV型阴极电泳涂料即UV光固化改性丙烯酸水性阴极电泳涂料工作液;
(6)以上述UV型阴极电泳涂料为工作液(阴极电泳工作液),将阴极电泳工作液加入电泳槽中,以200r/min转速进行搅拌;用洁净的铝合金板作为阳极,用乙醇和丙酮清洗后的5×7.5cm磷化板(磷化处理的铁板)作为阴极,两者同等程度地浸入工作液中,调整板间距为12cm;调节电源电压100V后,电泳180s后断开电源;使用去离子水清洗阴极板表面浮液,沥干后置于鼓风干燥箱在90℃干燥3min,去除表面水分;待极板降温后,将其放置于2000W的UV灯下照射50s,获得表面光滑平整的电泳制品。
所述电泳沉积层厚度为14μm。铅笔硬度为5H,耐热性为100℃保持性能不变,光泽度为80,耐丁酮擦拭次数为200,附着力为0级。
实施例4
(1)将2-萘甲醛(0.4mol)、丙烯酸甲酯(0.6mol)、4-二甲氨基吡啶(0.5mol)以及有机溶剂二甲基甲酰胺(200ml)混合均匀,在常温下搅拌72h,通过薄层色谱法TLC监控反应是否完成,反应结束后,用去离子水(300ml)水洗溶解,随后用乙酸乙酯(50ml)萃取,将有机相加入无水碳酸钠(10g)干燥10h后过滤,60℃减压旋蒸出溶剂,硅胶柱层析,60℃旋蒸,得到萘基改性化合物;
(2)将甲基丙烯酸二甲氨基乙酯(DMAEMA)25份、甲基丙烯酸甲酯(MMA)30份、丙烯酸羟乙酯(HEA)10份、丙烯酸丁酯(BA)30份、苯乙烯(St)15份、过氧化苯甲酰7份和有机溶剂甲基异丁基酮100份搅拌混合均匀,得到混合单体溶液;在搅拌的条件下(搅拌转速为200r/min),于85℃,向100份有机溶剂甲基异丁基酮中,滴加混合单体溶液,控制蠕动泵滴速15rpm,在3h内滴加完毕,保温6h,冷却后出料,40℃减压蒸馏到固含量为70%,得到产物A;
(3)将异佛尔酮二异氰酸酯(IPDI)20份和β-苯基萘胺1份混合均匀,然后在搅拌和70℃条件下,滴加由丙烯酸羟乙酯(HEA)10份和4-二甲氨基吡啶0.5份混合而成的混合物,通过蠕动泵,控制滴速8rpm,在1h内滴加完毕;滴加完毕后20min后用二正丁胺法滴定法(方法参考国标GBT 18446-2009)测定反应体系中-NCO含量,直至-NCO的含量达到半封闭后的理论值(-NCO,9.18%)的含量,终止反应,得到产物B;
(4)将4-二甲氨基吡啶0.5份、β-苯基萘胺1份溶于10份有机溶剂甲基异丁基酮中,得到催化剂和阻聚剂的混合溶液;将催化剂和阻聚剂的混合溶液与步骤(3)的产物B混合均匀,得到混合物;在搅拌的条件下(搅拌转速为150r/min),于50℃,向步骤(2)的产物A中滴加混合物,采用蠕动泵滴加,控制滴速8rpm,1h内滴加完毕,保温4h(使用傅立叶红外光谱仪表征分析,确保异氰酸根与羟基反应完全),得到树脂产物;
(5)于70℃,向步骤(4)的树脂产物加入二羟基甲基丙酸10份,以200r/min的搅拌速度搅拌60min;然后降至室温,加入丙二醇单丙醚8份、2-羟基-2-甲基-1-[4-(2-羟基乙氧基)苯基]-1-丙酮8份和萘基改性化合物30份,以250r/min搅拌5min,使其分散均匀;分三次逐渐加入去离子水至固含量降低为10%,用高速分散机进行乳化分散(6000r/min转速下分散20min),以150r/min熟化24h,得到UV型阴极电泳涂料即UV光固化改性丙烯酸水性阴极电泳涂料工作液;
(6)以上述UV型阴极电泳涂料为工作液(阴极电泳工作液),将阴极电泳工作液加入电泳槽中,以250r/min转速进行搅拌;用洁净的铝合金板作为阳极,用乙醇和丙酮清洗后的5×7.5cm磷化板(磷化处理的铁板)作为阴极,两者同等程度地浸入工作液中,调整板间距为15cm;调节电源电压100V后,电泳180s后断开电源;使用去离子水清洗阴极板表面浮液,沥干后置于鼓风干燥箱在100℃干燥3min,去除表面水分;待极板降温后,将其放置于2000W的UV灯下照射10s,获得表面光滑平整的电泳制品。
所述电泳沉积层厚度为15μm,铅笔硬度为5H,耐热性为100℃保持性能不变,光泽度为80,耐丁酮擦拭次数为150,附着力为0级。
对比例5
①制备甲基丙烯酸二甲氨基乙酯改性丙烯酸树脂
在装有搅拌棒、回流冷凝管、温度计的四口烧瓶中,加入60g丙二醇甲醚醋酸酯,在100℃下,滴入由15g(占14wt%)甲基丙烯酸二甲氨基乙酯、18g(占17wt%)含羟基的(甲基)丙烯酸酯类单体((甲基)丙烯酸-2-羟基丙酯)、其它丙烯酸酯类单体74g(占69wt%,包括24g甲基丙烯酸甲酯、30g甲基丙烯酸异冰片酯、20g甲基丙烯酸丁酯)及单体总量3wt%的偶氮二异丁腈(3.21g)组成的混合物,3小时滴加完毕,保温反应3小时,使单体转化率达98%以上,制得甲基丙烯酸二甲氨基乙酯改性丙烯酸树脂;
②制备含双键单体封闭改性的异氰酸酯
将1摩尔的异佛尔酮二异氰酸酯与和0.7摩尔的丙烯酸-2羟基丙酯,在月桂酸二丁基锡催化剂作用下,于60℃,反应3小时,制得含双键单体封闭改性的异氰酸酯;
③制备阳离子化的具有聚合活性的树脂
将0.5摩尔步骤②制得的含双键单体封闭改性的异氰酸酯加到1摩尔步骤①制得的甲基丙烯酸二甲氨基乙酯改性丙烯酸酯中,在催化剂作用下,80~90℃反应3小时,升温至100℃保温0.5小时,然后用醋酸中和至pH为5.0~5.5,制得阳离子化的具有聚合活性的树脂;
④制备紫外光固化阴极电泳涂料组合物
取步骤③制得的阳离子化的具有聚合活性的树脂100g,加上3g光引发剂(1-羟基环已烷苯甲酮0.6g和2-羟基-2-甲基-1-苯基丙酮2.4g),再加入具有光学活性的化合物二官能团丙烯酸酯(1,6-己二醇二丙烯酸酯)5g和具有光学活性的低聚物脂肪族聚氨酯丙烯酸酯(EBECRYL8602)10g,共计15g,搅拌混合均匀,即得到紫外光固化阴极电泳涂料组合物,其固体含量为60wt%。
实验结果:涂膜外观好,耐溶剂MEK擦拭50次固化时间为25s,漆膜硬度为4H,光泽度为60,90℃下不分解。
以上所述1~4仅为本发明的实施例,5为对比实施例,从实施例1~4与对比实施例5的性能对比中,萘基改性化合物制备的UV阴极电泳涂料的耐热性能有显著提升,对于电泳涂料的并非因此限制本发明保护的范围,凡是利用本发明说明书内容的等效结构或者等效流程变换,或直接或间接运用在其他相关的技术领域,均同理包括在本发明的专利保护范围内。
Claims (10)
1.一种萘基改性化合物,其特征在于:其结构式为式I
2.根据权利要求1所述萘基改性化合物的制备方法,其特征在于:以有机溶剂为反应介质,以2-萘甲醛和丙烯酸甲酯为反应原料,在催化剂的作用下反应原料进行反应,纯化,得到萘基改性化合物。
3.根据权利要求2所述萘基改性化合物的制备方法,其特征在于:所述2-萘甲醛与丙烯酸甲酯的摩尔比为(0.1~0.4)mol:(0.2~0.6)mol;
所述2-萘甲醛与催化剂的用量比为(0.1~0.4)mol:(0.1~0.5)mol;所述2-萘甲醛与有机溶剂的用量比为(0.1~0.4)mol:(50~200)ml;
所述催化剂为三乙胺、三乙烯二胺、四丁基硫酸氢胺、四丁基溴化胺、三乙基苄基氯化胺、4-二甲氨基吡啶中的一种以上;所述有机溶剂为四氢呋喃、乙酸乙酯、甲醇、二甲基亚砜、二甲基甲酰胺中的一种以上;
所述反应的温度为常温,所述反应通过薄层色谱法TLC监控反应是否完成。
4.一种UV型阴极电泳涂料利用权利要求1所述萘基改性化合物制备而成。
5.根据权利要求4所述UV型阴极电泳涂料,其特征在于:由以下按重量份的组分组成:甲基丙烯酸二甲氨基乙酯10~25份、甲基丙烯酸甲酯15~30份、丙烯酸羟乙酯4~20份、丙烯酸丁酯15~30份、苯乙烯5~20份、二异氰酸酯5~20份、催化剂0.2~1份、阻聚剂1~2份、自由基引发剂1~10份、分散剂2~8份、光引发剂2~8份、萘基改性化合物5~30份、中和剂3~10份、有机溶剂102~210份、水100~1500份。
6.根据权利要求5所述UV型阴极电泳涂料,其特征在于:所述二异氰酸酯为异佛尔酮二异氰酸酯;
所述催化剂为三乙胺、二月桂酸二丁基锡、三乙烯二胺、四丁基硫酸氢胺、四丁基溴化胺、三乙基苄基氯化胺、4-二甲氨基吡啶中的一种以上;
所述阻聚剂为对苯二酚、对苯醌、2,6-二叔丁基对甲苯酚、β-苯基萘胺、对叔丁基邻苯二酚中的一种以上;
所述自由基引发剂为偶氮二异丁腈、偶氮二异丁酸二甲酯、过氧化苯甲酰中的一种以上;
所述分散剂为乙二醇单丁醚、丙烯乙二醇单丁醚、丙二醇单丙醚、丙二醇单丁醚中的一种以上;
所述光引发剂为1-羟基环己基苯基甲酮、2-羟基-2-甲基-1-苯基丙酮、2,4,6-三甲基苯甲酰基-二苯基氧化膦、2-羟基-2-甲基-1-[4-(2-羟基乙氧基)苯基]-1-丙酮中的一种以上;
所述中和剂为乳酸、冰醋酸、硝酸、二羟基甲基丙酸中的一种以上;
所述有机溶剂为丙二醇甲醚醋酸酯、乙酸乙酯、甲醇、二甲基亚砜、甲基异丁基酮中的一种以上。
7.根据权利要求4~6任一项所述UV型阴极电泳涂料的制备方法,其特征在于:包括以下步骤:
(1)将甲基丙烯酸二甲氨基乙酯10~25份、甲基丙烯酸甲酯15~30份、丙烯酸羟乙酯2~10份、丙烯酸丁酯15~30份、苯乙烯5~20份、自由基引发剂1~10份和有机溶剂50~100份混合均匀,得到混合单体溶液;在搅拌的条件下,于70℃~90℃,向50~100份有机溶剂中,滴加混合单体溶液,滴加完毕后保温4~6h,减压蒸馏至固含量为50wt%~70wt%,得到产物A;
(2)将二异氰酸酯5~20份和阻聚剂0.5~1份混合均匀,然后在40~70℃下,滴加由丙烯酸羟乙酯2~10份和催化剂0.1~0.5份混合而成的混合物,滴加完后,持续反应,当反应体系中-NCO的含量达到半封闭后的理论值的含量时,终止反应,得到产物B;
(3)将催化剂0.1~0.5份、阻聚剂0.5~1份溶于2~10份有机溶剂中,得到催化剂和阻聚剂的混合溶液;将催化剂和阻聚剂的混合溶液与步骤(2)的产物B混合均匀,得到混合物;在搅拌的条件下,于40℃~70℃,向步骤(1)的产物A中滴加混合物,滴加完毕,保温3~4h,得到树脂产物;
(4)于40℃~70℃,向步骤(3)的树脂产物加入中和剂3~10份,搅拌均匀,降至室温,加入分散剂2~8份、光引发剂2~8份和萘基改性化合物5~30份,分散均匀,逐步加入100~1500份水使得固含量为10~20%,高速乳化分散,熟化,得到UV型阴极电泳涂料。
8.根据权利要求7所述UV型阴极电泳涂料的制备方法,其特征在于:步骤(4)中所述高速乳化分散的条件为3000~6000r/min转速下分散20~60min,熟化的条件为以150~250r/min熟化24~48h。
9.根据权利要求4~6任一项所述UV型阴极电泳涂料的应用,其特征在于:所述UV型阴极电泳涂料用于制备电泳制品。
10.根据权利要求9所述的应用,其特征在于:所述电泳制品的具体制备方法为:以UV型阴极电泳涂料为工作液,以铝合金板作为阳极,以基底极板为阴极,进行电泳处理,清洗,干燥,UV灯照射,得到电泳制品;
所述阴极和阳极的间距为8~15cm;所述电泳的电源电压100~150V,电泳的时间为60~180s;所述UV灯照射的条件为于1000W~2000W的UV灯下照射10~60s。
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