CN103282110B - 分散剂和分散体组合物 - Google Patents
分散剂和分散体组合物 Download PDFInfo
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- CN103282110B CN103282110B CN201180062579.9A CN201180062579A CN103282110B CN 103282110 B CN103282110 B CN 103282110B CN 201180062579 A CN201180062579 A CN 201180062579A CN 103282110 B CN103282110 B CN 103282110B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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Abstract
本发明提供能够适用于广泛范围的分散质,少量添加即能够发挥优异的分散稳定性的非水性分散介质用分散剂。该分散剂是含有下述(1)表示的化合物的分散剂,
Description
技术领域
本发明涉及分散剂和使用该分散剂形成的分散体组合物。
背景技术
来自无机物或来自有机物的各向同性材料和/或各向异性材料在混杂材料、表面保护剂、导电膏、导电墨水、传感器、精密分析元件、光存储器、液晶显示元件、纳米磁体、传热介质、燃料电池用高性能催化剂、有机太阳能电池、纳米玻璃设备、研磨剂、药物载体、环境催化剂、涂料、印刷墨水、喷墨用墨水、滤色器用抗蚀剂、书写用具用墨水等用途领域中作为主体材料使用。此时,上述来自无机物或者来自有机物的各向同性材料和/或各向异性材料在水性分散介质或非水性分散介质中作为微小颗粒调制成分散体来利用,从而有效提高加工性能、产品性能和原料物性,在产业上被用作有望实现品质稳定化和制造时的成品率提高的物质。
另一方面,分散质的原料变更、颗粒尺寸的微小化及定向形状控制存在着使分散质的稳定分散难以施行、分散质在分散介质中短时间内即产生凝集的问题。分散质的凝集在分散体的制造中不仅会导致生产率降低、加工性能降低、操作性能降低以及成品率降低,还会引起最终产品的产品性能、原料物性和品质的降低。此外,外观上也会出现透明性、光泽、着色力的降低,产生色散以及裂纹等不良现象。为了抑制这样的分散质的凝集并实现分散稳定化而使用分散剂。
作为已提出过的低分子量分散剂,具有羧基的有机化合物除了例如甲酸、乙酸、丙酸、丁酸、己酸、庚酸、辛酸、壬酸、癸酸、十一烷酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、油酸、亚油酸、亚麻酸等碳原子数1~20的饱和及不饱和羧酸类之外,还包括羟基羧酸类、碳原子数6~34的脂环族或芳香族羧酸类等。烯基琥珀酸酐类包括辛烯基琥珀酸酐、十二碳烯基琥珀酸酐、十六碳烯基琥珀酸酐等。具有硫醇基的有机化合物包括例如巯基乙醇、巯基-2-丙醇、1-巯基-2,3-丙二醇、3-巯基丙基三甲氧基硅烷、巯基琥珀酸、己硫醇、戊二硫醇、十二烷硫醇、十一烷硫醇、癸硫醇等烷基硫醇。具有酚环的有机化合物包括例如三苯基膦、三丁基膦、三辛基膦、三丁基膦等。具有氨基的有机化合物包括例如丙胺、丁胺、己胺、庚胺、辛胺、2-乙基己胺、壬胺、癸胺、十二烷基胺、十六烷基胺、油胺等。此外,作为高分子量分散剂,主要是作为颜料等的分散剂而被开发的具有羧基、氨基、羟基、酯键、酰胺键、芳香环、杂环等骨架的高分子型分散剂也可转用于本用途中,市售产品有Byk Chemie公司制DISPERBYK系列、EFKAAdditives公司制Ciba EFKA系列、Lubrizol公司制Solsperse系列、楠本化成公司制DISPARLON系列等。
此外,也提出有将现存的表面活性剂用作分散剂的方案,作为阴离子表面活性剂,例如有高级脂肪酸盐、烷基磺酸盐、α-烯烃磺酸盐、链烷烃磺酸盐、烷基苯磺酸盐、磺基琥珀酸酯盐、烷基硫酸酯盐、烷基醚硫酸酯盐、烷基磷酸酯盐、烷基醚磷酸酯盐、烷基醚碳酸盐、α-磺基脂肪酸甲酯盐、甲基牛磺酸盐等。作为非离子表面活性剂,例如有甘油脂肪酸酯、聚甘油脂肪酸酯、蔗糖脂肪酸酯、脱水山梨糖醇脂肪酸酯、聚氧乙烯失水山梨糖醇脂肪酸酯、聚氧乙烯烷基醚、聚氧乙烯烷基苯基醚、聚氧乙烯脂肪酸酯、脂肪酸烷醇酰胺、烷基糖苷等。作为两性表面活性剂,例如有烷基甜菜碱、脂肪酰胺丙基甜菜碱、烷基氧化胺等。作为阳离子表面活性剂,例如有烷基三甲基铵盐、二烷基二甲基铵盐、烷基二甲基苄基铵盐、烷基吡啶鎓盐等。此外,还有氟类表面活性剂或纤维素衍生物、多羧酸盐、聚苯乙烯磺酸盐等高分子表面活性剂。
尽管进行了使用上述已有分散剂来抑制分散体的凝集以得到稳定的分散体组合物的研究,但是,在分散介质、分散质的多样化,分散质的颗粒尺寸的微小化、形状的多样化,最终产品的高品质化、生产率提高、加工性能的高要求等方面,已提出的分散剂尚未充分满足所需求的性能。
例如,在分散介质为水的情况下,对基于分散剂的疏水性相互作用的表面吸附作用、离子性基团所带来的电吸附作用、来自芳香环的π电子相互作用,还有粒子之间形成电偶极子层所带来的粒子之间的静电推斥作用的利用,以及形成空间位阻所带来的分散稳定化作用,或者作为稳定剂添加保护胶体、增稠剂等均是有效的,可采用能够实现分散稳定化和抑制凝集的多种方案。
另一方面,在非水性分散介质的情况下,疏水性相互作用、离子性基团所带来的表面电吸附作用、静电推斥作用的效果极其有限,因此,分散剂的在分散颗粒的表面吸附很大程度上取决于分散质颗粒与分散剂的特定部位之间的酸碱相互作用。即,实际上,分散剂的选择是根据分散质的表面性能来进行个别优化,分散剂的用途处于受到极大限制的状况,而且,实际上分散剂相对于与之一起使用的分散介质的亲和性也需要综合考虑所使用的分散介质来进行最优分散剂的个别选择。
尽管上述各种离子性表面活性剂作为水系分散剂非常有效,但是其中多为不溶于非水系分散介质的成分,其适用范围受到极大限制。
分散质颗粒的大小为微米级尺寸的情况下,由于能够采用多个吸附点进行多点吸附,或者通过形成空间位阻的高密度的厚保护层来设计分散体系,从而适合选择高分子量分散剂。但在分散质颗粒的大小为纳米级或亚纳米级尺寸的情况下,基于分散质颗粒的大小和分散剂分子的大小的差异难以实现利用高分子量分散剂的分散体系设计或者设计受限。即,当使用分子大小相对于分散质颗粒的大小明显较大的高分子量分散剂时,会发生分散质颗粒和分散剂之间、分散剂的分子和分散剂的分子之间的多点吸附或者缠结或交联,促进了分散质颗粒的凝集,因此,在分散稳定化方面具有本质问题。
再者,为了实现分散稳定化,常规方法是利用分散质颗粒和分散剂之间的更强的相互作用来进行分散体系的设计,但是,除了分散介质的置换及极性变更、确保分散体组合物的力学或化学稳定性、分散质颗粒的清出、成膜化(能够以低温且较短时间形成高光泽度的膜的成膜性)之外,还要求兼具有在除去分散剂时易于从分散剂表面脱离的易解吸性的性能,这对于最终产品的生产率提高、加工性能和品质稳定而言是重要因素。在这一点上,已有的分散剂也不是能够充分满足要求性能的制品。
另外,树脂中分散有微小的纳米尺寸的无机颗粒(粒径1~100nm)或有机填料、颜料等的复合材料被称为聚合物纳米复合材料,可以预见通过复合实现了折射率提高等效果,能够用于光学材料用途。但是,纳米尺寸的颗粒容易凝集、与树脂的亲和性低,因此极难在树脂中均匀分散。就将纳米尺寸的颗粒均匀分散在树脂中而言,利用水性分散介质非常困难或者受限,所以通常采用使用分散剂调制纳米颗粒在非水性分散介质中均匀分散的分散体,使树脂溶解混合在该分散体中的方法,或者将树脂溶解在溶剂中的溶液状态的产物与上述分散体混合,使之溶解和分散的方法是很有效的。作为这样的分散剂的例子,可以使用上述专利中所举出的聚氧乙烯烷基磷酸、聚氧乙烯烷基羧酸盐(专利文献1)。
此外,作为用于使金属颗粒、金属氧化物、颜料、各种填料类能够轻易地再分散到分散介质或树脂中的预处理,已知有用表面改性剂或表面保护剂覆盖分散质颗粒、或者使表面改性剂等浸渍到分散质颗粒中来利用的技术,但是,在先技术中多会对分散介质的种类或分散质的添加量有所限制,应用范围极其受限,而尚未找到解决该问题的分散剂或者表面改性剂、表面保护剂。如果能够找到可以解决上述问题的分散剂,即,如能找到分散介质的种类及分散质的添加量不受限制,对广泛原料具有通用性的分散剂,得到使用该分散剂的非水性分散体,或将该分散剂用作分散质的表面改性剂或表面保护剂,得到由该分散剂覆盖或者浸渍有该分散剂的粉状、粒状或膏状的产物,就将在溶剂的置换及极性变更、与树脂、树脂溶液的混合等方面产生极大的产业利用价值。
例如,作为这类在先技术,在专利文献2中公开了一种含有金属纳米颗粒(A)和覆盖该金属纳米颗粒(A)的保护胶体(B)的金属胶体颗粒,上述保护胶体(B)是含有具有羧基的有机化合物(B1)和高分子分散剂(B2)的金属胶体颗粒。
此外,本申请提出时尚未公开的日本特愿2010-120122号中,记载了一种含有具有支链的烷基和/或链烯基的非水性分散介质用分散剂。如果使用该分散剂,就能够适用于很宽范围内的分散质,添加很少的量就能够发挥优异的分散稳定性。但是,人们对能够分散更多量的无机微粒和填料等分散质的分散剂的开发仍有需求。
在先技术文献
专利文献
专利文献1:日本特开2004-354568号公报
专利文献2:日本特开2009-74171号公报
发明内容
发明要解决的课题
上述现有技术的聚氧化乙烯烷基磷酸、聚氧乙烯烷基羧酸盐的使用会因无机微粒与树脂或者填料与树脂的结合而出现无法得到期望的分散性的情况。例如,聚氧乙烯烷基羧酸与作为芳香族类通用光固化型树脂材料的苯氧乙基丙烯酸酯(PHE)的组合制作的分散液出现了透明性明显消失、分散性降低。基于这样的理由,需要能够将无机微粒分散在各种树脂中的分散剂。
本发明是鉴于现有技术所具有的上述问题而做出,其目的在于提供能够适用于广泛范围的分散质、少量添加即能够发挥优异的分散稳定性、且适用于大量分散质的分散的介质分散用分散剂。另外,本发明的目的还在于提供使用该分散剂形成的分散体组合物。而且,本发明的目的还在于提供由该分散剂覆盖或者浸渍有该分散剂而得到的有机物颗粒或无机物颗粒。
解决课题的手段
为了实现上述目的,本发明的分散剂为含有下述(1)表示的化合物的分散剂。
其中,式(1)中的R表示含有至少一个以上的芳香环的烃基;式(1)中的AO表示碳原子数1~4的氧化烯基;n表示氧化烯的平均加成摩尔数,其为1~30的范围内的数值;式(1)中的X为含有O原子、S原子、—NR1—(R1为H原子或者为含有C原子、H原子、O原子中的任意原子的基团)中的任意基团的连接基,式(1)中的Y为含有C、H、O原子中的任意基团的连接基。
在此,式(1)中的R优选为下述式(2)所示的苯乙烯化苯基。
其中,式(2)中的k为平均值,其为1~5的范围内的数值。
式(1)中的Y优选为碳原子数1~15的亚烷基,或下述式(3)所示的官能团。
其中,式(3)中的Z表示选自碳原子数1~15的亚烷基、亚乙烯基、亚苯基以及含有羧基的亚苯基中的任一个。
本发明的无机物颗粒是被上述任一所述分散剂覆盖或者含浸有该分散剂的颗粒。
本发明的分散体组合物是使用上述任一所述分散剂,在非水性分散介质中将无机物颗粒分散而得的组合物。
另外,本发明的涂料组合物是含有作为非水性分散介质使用了树脂的上述分散体组合物的涂料组合物。
另外,本发明的分散体组合物是含有作为非水性分散介质使用了溶剂的上述分散体组合物与树脂的混合物的组合物。
本发明的部件是在基材上涂敷任一上述涂料组合物之后,通过反应得到的部件。
发明的效果
根据本发明,能够将无机微粒或者填料分散到现有分散剂的情况下难以分散的分散介质中,提供透明性高的稳定的分散体组合物。此外,还能够提供少量添加即能够稳定分散大量分散质的分散剂。另外,还能够提供使用该分散剂形成的分散体组合物和含有该分散体组合物的涂料组合物。
具体实施方式
本发明的分散剂如式(1)所示,包括含有至少一个以上的芳香环的烃基的分散介质亲和性部位、和含有氧化烯基以及羧基的分散质亲和性部位,分散介质亲和性部位和分散质亲和性部位通过连接基X连接。下面对本发明的优选实施方式进行详细说明。
1.关于疏水基(R)
在能够用于本发明的分散剂的疏水基(R)中,R为含有至少一个以上的芳香环的烃基,具体而言,除了上述式(2)表示的苯乙烯化苯基以外,还可举出含有辛基苯基、壬基苯基、枯烯基苯基、邻苯基-苯基、对苯基-苯基等的官能团。还能够举出含有萘基、蒽基、苯并芘、苯并菲、六苯并苯、碗状分子碗烯(Corannulene)、萘并萘、芘、三亚苯等多环芳香烃的官能团。另外,在本申请中,例如,萘被视为含有2个芳香环的化合物,蒽被视为含有3个芳香环的化合物。在本发明的分散剂中,芳香环被认为大大有助于分散性的提高。这些官能团中,为了实现本发明的目的,优选使用式(2)表示的含有苯乙烯化苯基的化合物。
2.连接基(X)
连接基(X)为含有O原子、S原子、—NR1—中的任意基团的连接基,R1为H原子或含有C原子、H原子、O原子中的任意原子的基团。作为R1,例如可以举出正己基、正辛基等碳原子数1~18的饱和直链烷基,2-乙基己基、异癸基等碳原子数1~18的饱和支链烷基,亚油基、亚麻基、油基、椰油烷基、牛脂烷基、固化牛脂烷基等不饱和长链烷基。
3.氧化烯基(AO)n
本发明的分散剂适宜选择的氧化烯基是式(1)中以AO表示的碳原子数1~4的氧化烯基,具体而言,碳原子数为2的氧化烯基是氧化乙烯。碳原子数为3的氧化烯基为氧化丙烯。碳原子数为4的氧化烯基为四氢呋喃或氧化丁烯,优选为1,2-氧化丁烯或2,3-氧化丁烯。在本发明的分散剂中,氧化烯链(—(AO)n—)在调节分散剂的分散介质亲和性的目的下,氧化烯基既可以是均聚链,也可以是两种以上的氧化烯的无规共聚链或嵌段共聚链,此外,还可以是其组合。式(1)的表示氧化烯基的平均加成摩尔数的n为1~30的范围,优选为3~20的范围。
4.连接基(Y)
连接基(Y)可从具有碳原子、氢原子、氧原子的公知结构中选择,优选为饱和烃基、不饱和烃基、醚基、羰基、酯基,可以具有脂环结构、芳香环结构,且还可以具有重复单元。由于连接基Y在含有氮原子和/或硫原子和/或磷原子等的情况下,具有减弱羧基与分散质的亲和效果的作用,因此,这样的结构不适于用作本发明的分散剂的结构因子。
此外,式(1)中的Y优选为碳原子数1~15的亚烷基,更优选为碳原子数为1~8的亚烷基。
式(1)的Y优选为上述式(3)表示的物质。其中,在式(3)中,Z为选自碳原子数1~15的亚烷基、亚乙烯基、亚苯基以及含有羧基的亚苯基中的任一个。
5.分散质颗粒
由本发明的分散剂分散的分散质颗粒能够从来自无机物的颗粒和/或来自有机物的颗粒中选择。例如,作为来自无机物的颗粒,能够使用铁、铝、铬、镍、钴、锌、钨、铟、锡、钯、锆、钛、铜、银、金、铂等及其合金,或者它们的混合物。此时,为了从介质中稳定地清出上述金属颗粒,可以用链烷酸类或脂肪酸类、羟基羧酸类、脂环族羧酸类、芳香族羧酸类、烯烃琥珀酸酐类、硫醇类、酚衍生物类、两亲性聚合物、高分子表面活性剂、低分子表面活性剂等保护剂覆盖。此外,还有高岭土、粘土、滑石、云母、膨润土、白云石、硅酸钙、硅酸镁、石棉、碳酸钙、碳酸镁、碳酸钡、硫酸钙、硫酸钡、硫酸铝、氢氧化铝、氢氧化铁、硅酸铝、氧化锆、氧化镁、氧化铝、氧化钛、氧化铁、氧化锌、三氧化锑、氧化铟、氧化铟锡、碳化硅、氮化硅、氮化硼、钛酸钡、硅藻土、炭黑、石墨、矿棉、玻璃棉、玻璃纤维、碳纤维、碳纳米纤维、碳纳米管(单壁碳纳米管、双壁碳纳米管、多壁碳纳米管)等。此外,作为来自有机物的颗粒,可以举出偶氮类、重氮类、缩合偶氮类、硫靛类、阴丹士林类、喹吖啶酮类、蒽醌类、苯并咪唑酮类、二萘嵌苯类、酞菁类、蒽吡啶类(anthrapyridine)、二噁嗪类颜料等有机颜料;聚乙烯树脂、聚丙烯树脂、聚酯树脂、尼龙树脂、聚酰胺树脂、芳族聚酰胺树脂、丙烯酸树脂、维尼纶树脂、聚氨酯树脂、三聚氰胺树脂、聚苯乙烯树脂、聚乳酸、醋酸纤维、纤维素、半纤维素、木质素、甲壳素、淀粉、聚缩醛、芳族聚酰胺树脂、聚碳酸酯、聚苯醚、聚醚醚酮、聚醚酮-聚对苯二甲酸丁二酯、聚萘二甲酸乙二酯、聚萘二甲酸丁二酯、聚砜、聚苯硫醚、聚酰亚胺等。通过本发明的分散剂分散的上述分散质颗粒既可以是结晶状,也可以是非晶状。此外,通过本发明的分散剂分散的上述分散质颗粒既可以是各向同性颗粒,也可以是各向异性颗粒,还可以是纤维状。
在本发明中作为分散质的上述分散质颗粒能够采用可由公知方法得到的颗粒。作为微粒的调制方法,有将粗大颗粒机械粉碎,使其微细化的自顶向下(Top-down)方式;和生成多种单位颗粒,经由单位颗粒凝集的聚集态而形成颗粒的自底向上(Bottom-up)方式这两种方式,但由任一种方法调制的制品均适合采用。此外,这些颗粒也可以是通过湿式法、干式法中的任一方法得到。此外,自底向上方式包括物理方法和化学方法,可采用其中任一种方法。本发明的分散剂既可以用于将粗大颗粒机械粉碎,使其微细化的自顶向下方式的工艺,也可以用于生成多种单位颗粒,经由单位颗粒凝集的聚集态而形成颗粒的自底向上的工艺。或者,还可以使用事先用上述方法调制出微粒之后,为了从介质中稳定清出该分散质颗粒,用被称为表面改性剂或表面保护剂的公知的保护剂包覆或使该保护剂浸渍于其中而被清出的颗粒。也可将上述公知分散剂代为用作保护剂。
为了更具体地说明自底向上方式,举出了上述分散质颗粒中的金属纳米颗粒的调制方法例。作为自底向上方式中的物理方法的代表例,有使基体金属(bulk metal)在不活泼气体中蒸发,利用其与气体的碰撞使其冷却冷凝,生成纳米颗粒的气体中蒸发法。此外,化学方法则有在保护剂的存在下,在液相中还原金属离子,使生成的零价金属在纳米尺寸下稳定的液相还原法及金属配位化合物的热解法等。作为液相还原法,可利用化学还原法、电化学还原法、光还原法或化学还原法与光照射法的组合方法等。
此外,可适用于本发明的分散质颗粒,如上所述,可以是由自顶向下方式、自底向上方式中的任一种方法得到的颗粒,这些颗粒可以是在水系、非水系、气相中的任一种环境下调制而得的颗粒。
6.分散剂
作为能够用于本发明的分散介质,可以举出甲苯、二甲苯、芳香烃类溶剂、正己烷、环己烷、正庚烷等烃类溶剂;二氯甲烷、氯仿、二氯乙烷等卤化烃类溶剂;乙醚、异丙醚、二噁烷、四氢呋喃、二丁醚、丁基乙基醚、甲基叔丁基醚、松油基甲基醚、二氢松油基甲基醚、二甘醇二甲醚、1,3-二氧戊环等醚类溶剂;丙酮、苯乙酮、丁酮、甲基丙基酮、二乙基酮、甲基-正丁基酮、甲基异丁基酮、二丙基酮、二异丁基酮、甲基戊基酮、丙酮基丙酮、异佛尔酮、环己酮、甲基环己酮、2-(1-环己烯基)环己酮甲基异丁基酮、环己酮、异佛尔酮等酮类溶剂;甲酸乙酯、甲酸丙酯、甲酸丁酯、甲酸异丁酯、甲酸戊酯、乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸异戊酯、乙酸环己酯、乳酸乙酯、乙酸-3-甲氧基丁酯、乙酸仲己酯、乙酸-2-乙基丁酯、乙酸-2-乙基己酯、乙酸苄酯、丙酸甲酯、丙酸乙酯、单氯乙酸甲酯、单氯乙酸乙酯、单氯乙酸丁酯、乙酰乙酸甲酯、乙酰乙酸乙酯、丙酸丁酯、丙酸异戊酯、γ-丁内酯等酯类溶剂;乙二醇单乙醚、乙二醇单异丙醚、乙二醇单丁醚、二乙二醇单乙醚、二乙二醇单正丁醚、丙二醇单甲醚、丙二醇单乙醚、丙二醇单正丙醚、丙二醇单正丁醚、二丙二醇单甲醚、二丙二醇单乙醚、二丙二醇单正丙醚、二丙二醇单正丁醚、三乙二醇单甲醚、三乙二醇单乙醚、三乙二醇单正丙醚、三乙二醇单正丁醚、三丙二醇单乙醚、三丙二醇单正丙醚、三丙二醇单正丁醚等二醇醚类溶剂,以及这些单醚类的乙酸乙酯类溶剂;二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲基异丁醚、二丙二醇二甲醚、二丙二醇二乙醚等二烷基醚类溶剂。
此外,还可以举出甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、庚醇、正戊醇、仲戊醇、正己醇、四羟基糠醇、糠醇、烯丙醇、氯乙醇、辛基十二烷醇、1-乙基-1-丙醇、2-甲基-1-丁醇、异戊醇、叔戊醇、仲异戊醇、新戊醇、己醇、2-甲基-1-戊醇、4-甲基-2-戊醇、庚醇、正辛醇、2-乙基-己醇、壬醇、癸醇、十一烷醇、月桂醇、环戊醇、环己醇、苄醇、α-松油醇、松油醇C、L-α-松油醇、二氢松油醇、松油基氧乙醇、二氢松油基氧乙醇、日本Terpene化学株式会社制Terusolve MTPH、Terusolve DTO-210、Terusolve THA-90、Terusolve THA-70、环己醇、3-甲氧基丁醇、双丙酮醇、1,4-丁二醇、辛二醇等,日产化学工业株式会社制Fine oxocol140N、Fine oxocol1600、Fine oxocol180、Fine oxocol180N、Fine oxocol2000等醇类溶剂、乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、1,3-丁二醇、己二醇、聚乙二醇、聚丙二醇等二醇类溶剂。
此外,还可以举出二甲基乙酰胺、二甲基甲酰胺等酰胺类溶剂等。此外,作为分散介质,也能够使用具有反应性基团的(甲基)丙烯酸、(甲基)丙烯酸酯类、乙酸乙烯酯等乙烯类单体、乙烯醚衍生物类、聚烯丙基衍生物等乙烯类不饱和单体类。此外,也能够没有特别限定地使用通常的涂料用及粘合用、成型用中所利用的各种树脂类、低聚物类、单体类。具体而言,可以举出丙烯酸树脂、聚酯树脂、醇酸树脂、聚氨酯树脂、有机硅树脂、氟树脂、环氧树脂、聚碳酸酯树脂、聚氯乙烯树脂、聚乙烯醇等。此外,上述分散介质可以单独使用一种,也可混合两种以上适当使用。此外,尽管本发明的分散剂是以提供在非水性环境下的微粒分散体为目的,但对于上述分散介质,无论是有意还是偶然,在微粒分散体的制造工艺中,或者根据目标用途的状况,或者在最终产品设计中,都不完全否定水的混入和混合。
7.其它
本发明的分散剂能够通过公知的方法制造,在上述范围内,通过特别限定的选定疏水基的种类、氧化烯基种类及其加成形态、加成摩尔量、连接基等选定最优组成,与公知的分散剂相比,能够分散更广泛种类的分散质,能够在更广泛的种类的分散介质中将分散质稳定分散,在这一点上,在产业上的利用价值很大。
本发明的分散剂通过公知的精制方法,能够减少所含有的离子种,特别是碱金属离子、碱土金属离子、重金属离子、卤离子各种离子的含量。分散剂中的离子种对分散体的分散稳定性、耐腐蚀性、抗氧化性、分散涂膜的电性能(导电性能、绝缘性能)、时效稳定性、耐热性、低湿性、耐候性具有很大的影响,因此,虽然能够适宜决定上述离子的含量,但优选在分散剂中低于10ppm。
适于本发明采用的分散剂的含量只要是能够将分散质在上述非水性分散介质中均匀分散即可,除此没有特别限定,根据用途不同,用量各异,不过如以分散体组合物的整体为100重量%,优选为在0.1~20重量%的范围内,分散质颗粒的含量优选在1~90重量%的范围内。另外,分散剂的含量相对于分散质颗粒优选在1~300重量%的范围内。当以分散体组合物的整体为100重量%时,分散介质的含量优选在1~99重量%的范围内。此外,分散质颗粒的平均粒径优选在1~500nm的范围内,更优选在1~100nm的范围内。
本发明的分散剂能够通过公知的方法制造。例如,能够通过以醇、胺、硫醇中加合烯化氧的通常的非离子表面活性剂化合物为原料,使用单卤化低级羧酸或其盐,在碱的存在下与烯化氧末端的羟基反应的方法,或者使用酸酐与烯化氧末端的羟基进行开环反应的方法制造,但是不限于这些方法。
此外,本发明的分散体组合物能够使用公知的搅拌方式、均化方式、分散化方式调制。作为能够采用的分散器的一例,可以举出双辊、三辊辊磨机,球磨机、振动球磨机等球磨机,涂料搅拌机,连续盘型珠磨机、连续环型珠磨机等珠磨装置,混砂机,喷磨机等。此外,还可以在超声波发生浴中进行分散处理。
另外,本发明的分散剂不仅对于在非水性分散介质中的分散质颗粒的分散稳定化与公知技术相比能够发挥优异的分散稳定化效果,并且能够作为将分散质颗粒从介质中稳定清出的保护剂使用。作为用于从介质中稳定清出分散质颗粒的保护剂的功能,可以举出抑制生成颗粒的凝集、对于向容器壁面吸附的抑制和防止污染、赋予易再分散性、防止金属颗粒的氧化、颗粒表面的表面改性、防止功能性表面的劣化、溶剂置换时和极性变更时的冲击的缓和、粉末流动性的改善、粉末固化的防止等。本发明的分散剂在上述功能方面优于公知的保护剂,通过适当选择最优的氧化乙烯的加成形态及其加成摩尔量、疏水基的种类、连接基等,与公知的保护剂相比,能够在更宽范围的分散介质中将所期望的分散质稳定分散。
作为涂敷含有将树脂用作非水性分散介质的本发明的分散体组合物的涂料组合物,或者含有将溶剂用作非水性分散介质的本发明的分散体组合物和树脂的混合物的涂料组合物的基材,例如能够使用玻璃、树脂膜、玻璃复合材料、陶瓷、金属板或钢板等。
实施例
下面说明本发明的实施例和比较例。需要说明的是,下文中表示配合量的“份”是指“重量份”,“%”表示“重量%”。不言而喻,本发明不限于下述实施例,在不脱离本发明的技术范围的范围内,能够进行适当变更及修正。
<分散剂的合成>
制造例1(苯乙烯化苯酚(k=3)氧化乙烯8摩尔加合物的合成)
在高压釜中加入苯乙烯化苯酚(k=3)415g(1摩尔)、氢氧化钾1g(0.018摩尔)进行均匀混合。然后在反应体系的温度为130℃的条件下,向反应体系中滴加352g(8摩尔)氧化乙烯。氧化乙烯的滴加结束后,在该温度下,将压力维持在0.1MPa进行1小时熟化,得到苯乙烯化苯酚8EO加合物。
制造例2(苯乙烯化苯酚(k=3)氧化乙烯14摩尔加合物的合成)
除了使制造例1中的氧化乙烯的添加量为616g(14摩尔)之外,用与制造例1同样的方法进行合成,得到苯乙烯化苯酚14EO加合物。
制造例3(分散剂1的合成)
在甲苯溶液中,在反应器中加入制造例1中得到的苯乙烯化苯酚(k=3)氧化乙烯8摩尔加合物767g(1摩尔)和单氯乙酸钠152g(1.3摩尔)搅拌至均匀。然后在反应体系的温度为60℃的条件下添加52g氢氧化钠,之后将反应体系的温度升高到80℃,进行3小时熟化。熟化之后冷却到50℃,在50℃的条件下滴加98%硫酸117g(1.2摩尔),由此得到白色悬浊溶液。接着用蒸馏水清洗该白色悬浊溶液,减压馏去溶剂,得到实施例1所述的分散剂1(R:苯乙烯化苯基(k=3),AO:氧化乙烯,n:8,X:O,Y:CH2)。
制造例4(实施例2的分散剂的合成)
除了在制造例3中使用苯乙烯化苯酚(k=3)氧化乙烯14摩尔加合物1020g(1摩尔)代替苯乙烯化苯酚(k=3)氧化乙烯8摩尔加合物以外,使用与制造例1同样的方法进行,得到实施例2所述的分散剂(R:苯乙烯化苯基(k=3),AO:氧化乙烯,n:14,X:O,Y:CH2)。
制造例5(实施例3的分散剂的合成)
使苯乙烯化苯酚(k=2)氧化乙烯8摩尔加合物654g(1摩尔)和琥珀酸酐100g(1摩尔)在120℃的温度下反应2小时,得到实施例3所述的分散剂(R:苯乙烯化苯基(k=2)、AO:氧化乙烯,n:8,X:O,Y:COCH2CH2)。
制造例6(实施例4的分散剂的合成)
除了在制造例3中使用苯乙烯化苯酚(k=2)氧化乙烯8摩尔加合物654g(1摩尔)代替苯乙烯化苯酚(k=3)氧化乙烯8摩尔加合物以外,使用与制造例1同样的方法进行,得到实施例4所述的分散剂4(R:苯乙烯化苯基(k=2),AO:氧化乙烯,n:8、X:O,Y:CH2)。
制造例7(比较例1的分散剂的合成)
除了在制造例3中,作为原料的EO加合物使用异十三烷醇氧化乙烯10摩尔加合物640g(1摩尔)代替苯乙烯化苯酚(k=3)氧化乙烯8摩尔加合物之外,使用与制造例3同样的方法进行,得到比较例3所述的分散剂(R:异癸基,AO:氧化乙烯,n:10,X:O,Y:CH2)。
另外,上述所示的各材料以及此外的实施例、比较例中所使用的材料全部使用市售材料。
<氧化锆的丙烯酸酯单体分散体的制作>
在100份的市售氧化锆分散体(堺化学公司制,商品名SZR-M,一次粒径3nm、含有30重量%的甲醇的分散体)中添加下表1所示的分散剂1.5份、苯氧乙基丙烯酸酯(第一工业制药公司生产的商品名Newfrontier PHE)或苯硫基乙基丙烯酸酯(DAELIN Chemical Co.Ltd制,商品名:Electromer HRI-01)或邻苯基苯氧乙基丙烯酸酯28.5份、3-甲氧基-3-甲基丁醇12份并混合,然后使用旋转式汽化器减压除去甲醇,得到氧化锆的丙烯酸酯单体分散体。邻苯基苯氧乙基丙烯酸酯使用市售材料制成分散体。
<分散体的性能评价>
a.外观的透明性
将氧化锆的丙烯酸酯单体分散体加入透明玻璃容器,在上述玻璃容器之下放置记录着以12号字打印的字母的纸,通过穿越该分散体是否能够辨别字母来评价分散体的透明性,评价基准如下。
○:分散体放入1cm深度的玻璃容器之后,能够看清12号字的字母文字。分散体透明。
×:分散体放入1cm深度的玻璃容器之后,无法看清12号字的字母文字。分散体有混浊。其结果示于表1。
b.分散体的粘度评价
使用E型粘度计(东机产业株式会社制,商品名RE-80R)在25℃的温度下测量分散性良好的氧化锆的丙烯酸酯单体分散体的粘度。其结果一并示于表1。
c.分散体的折射率评价
使用阿贝折光仪(Atago公司制,商品名NAR-1T)在25℃的温度下测量分散性良好的氧化锆的丙烯酸酯单体分散体的折射率。其结果一并示于表1。
表1
*1)苯乙烯化苯基的原料,为在苯酚中引入了k个苯乙烯单体后的苯乙烯化苯酚
由表1可知,使用了疏水基中含有芳香环、端基为羧酸的分散剂的实施例1~6显示出对于含有芳香族类的丙烯酸酯单体的分散质非常优异的分散性。另一方面,在疏水基不含芳香环的比较例1~3和6的情况下,在与实施例1~6相同的分散剂添加量的情况下,分散性差。而且,即使在疏水基含有芳香环的情况下,但在端基为羧酸钠盐的比较例4以及端基为醇的比较例5的情况下,对溶剂的分散性大大变差。由此可知,在本发明中,端基的羧酸与芳香环同样在分散性方面具有重要作用。
在实施例1~6所示的分散体中,通过分散剂和丙烯酸酯单体的组合,与不含稀释溶液的条件无关,均为粘度低达1400~4000mPa·sec的分散体。由于分散体的粘度低就容易在基材上涂敷,因此可以说产业价值很高。另外,实施例1~6所示的分散体的折射率为1.6~1.645,与原丙烯酸酯单体种相比均得到提高,因此,使用了本发明的分散剂和氧化锆的分散体组合物,能够实现透明性和高折射率性能优异的分散体组合物和涂敷材料。
产业实用性
本发明的分散体组合物能够用于混杂材料、表面保护剂、导电膏、导电墨水、传感器、精密分析元件、光存储器、液晶显示元件、纳米磁体、传热介质、燃料电池用高性能催化剂、有机太阳能电池、纳米玻璃设备、研磨剂、药物载体、环境催化剂、涂料、印刷墨水、喷墨用墨水、滤色器用抗蚀剂、书写用具用墨水、光学薄膜、粘合剂、防反射膜、硬质涂膜等领域。本发明的分散剂在非水性分散介质中将上述用途制品及其制造工艺中作为主体成分的纳米尺寸的来自无机物或者来自有机物的各向同性材料和/或各向异性材料稳定分散,抑制分散质在分散介质中的凝集,实现长时间的分散稳定化,因此在用于提高所期望的产品性能、加工性能、品质稳定化、生产率方面十分有效。
Claims (7)
1.一种分散剂,所述分散剂是下述(1)所示的化合物,
其中,式(1)中的R为下述式(2)所示的苯乙烯化苯基,
式(1)中的AO表示碳原子数1~4的氧化烯基,n表示氧化烯基的平均加成摩尔数,该n为1~30的范围内的数值,
式(1)中的X由O原子、S原子、—NR1—中的任意原子或基团构成,其中,R1为H原子或者为含有C原子、H原子、O原子中的任意原子的基团,
式(1)中的Y由饱和烃基、不饱和烃基、醚基、羰基、酯基中的任意基团构成,
式(2)中的k为平均值,为1~5的范围内的数值。
2.如权利要求1所述的分散剂,其特征在于,式(1)中的Y为碳原子数1~15的亚烷基,或者下述式(3)所示的官能团,
其中,式(3)中的Z表示选自碳原子数1~15的亚烷基、亚乙烯基、亚苯基以及含有羧基的亚苯基中的任一个。
3.一种无机物颗粒,其特征在于,所述无机物颗粒是被权利要求1或2所述的分散剂覆盖或者含浸有所述分散剂的颗粒。
4.一种分散体组合物,其特征在于,所述分散体组合物是使用权利要求1或2所述的分散剂,在非水性分散介质中将无机物颗粒分散而得的组合物。
5.一种涂料组合物,其特征在于,所述涂料组合物是含有作为非水性分散介质使用了树脂的权利要求4所述的分散体组合物的涂料组合物。
6.一种涂料组合物,其特征在于,所述涂料组合物是含有作为非水性分散介质使用了溶剂的权利要求4所述的分散体组合物与树脂的混合物的涂料组合物。
7.一种部件,其特征在于,所述部件是在基材上涂敷权利要求5或6所述的涂料组合物之后,通过反应得到的部件。
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