CN1227584A - 用于油墨和涂料的改性碳产品 - Google Patents
用于油墨和涂料的改性碳产品 Download PDFInfo
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- CN1227584A CN1227584A CN97197039A CN97197039A CN1227584A CN 1227584 A CN1227584 A CN 1227584A CN 97197039 A CN97197039 A CN 97197039A CN 97197039 A CN97197039 A CN 97197039A CN 1227584 A CN1227584 A CN 1227584A
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Abstract
公开的改性碳产品,它包括已连接至少一个有机基团的碳。该有机基团包括a)至少一个芳族基团或C1-C12烷基,和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物。有机基团的至少一个芳族基团或C1-C12烷基直接连接到碳上,有机基团的存在量为约0.10至约2.7μmol/m2使用的碳(基于碳的CTAB或t-面积),或其存在量应使改性碳产品具有的残余值大于约5wt%。还公开了一种含改性碳产品的水性和非水性油墨和涂料。还公开了一种提高油墨流动性的方法,包括将改性碳产品加入油墨中作为油墨的一部分,所述流动性通过玻板流动测量。此外,公开了含合适溶剂和包括已连接至少一个有机基团的碳的改性碳产品的非水性油墨和涂料配料,其中有机基团包括:a)至少一个芳族基团或C1-C12烷基和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物,其中有机基团以任意量存在。
Description
本发明领域
本发明涉及改性碳产品及含该改性碳产品的油墨和涂料。
相关技术的描述
目前,绝大部分黑色颜料为炭黑,如可以干燥粉末形式、挤水色浆或液体浓缩物形式用作着色剂的炉法炭黑。通常,着色剂的形式影响色彩、持久性、疏松性(bulk)、不透明度、光泽、流变性、最终用途和印刷质量。
目前所用的有很多分类的油墨。这些油墨的类型包括印刷油墨、紫外线固化油墨、圆珠笔油墨、和打印油墨。通常,油墨可通过凸版印刷、平版印刷、苯胺印刷、凹版印刷、丝网印刷、模板印刷、复印和静电印刷施用。因此可发现油墨在诸如报纸、杂志、商业折叠纸盒、书籍、波纹纸盒、纸袋、包装物、标签、金属容器、塑料容器、塑料膜、箔、层压制品、食品垫块、卫生纸、纺织品等中的最终用途。McGraw-Hill科学技术大全,Vol.7 p.159-164进一步提供了可市购的油墨类型和其用途,这部分内容这里都作为参考引入。
涂料也可包含颜料,并用于各种表面的装饰、防护和功能处理。这些表面包括线圈、金属、仪表、家具、硬质纤维板、木材和胶合板、船舶、维护表面、汽车、罐和纸板。某些涂料如海底管线上的那些涂料是用于防护目的的。其它诸如汽车外部涂料起到装饰和防护的双重目的。另一些涂料提供对船甲板或轿车座位的摩擦控制。某些涂料控制污染船底,其它涂料保护罐中的食物和饮料。硅片、印刷电路板、输送信号的导波纤维上的涂料,以及录象带和计算机磁盘上的磁性涂料属于所谓涂料在高科技上的应用。
用于含水油墨和涂料的水性漆料类型包括其中粘合剂溶于水的那些漆料,其中粘合剂以胶体形式分散的那些漆料,和其中乳化剂乳化形成乳胶的那些漆料。粘合剂与挥发性液体的混合物称为漆料,它可为溶液或细粘合剂颗粒在非溶剂中的分散体。颜料为分散于漆料中的并在最终薄膜中分布于整个粘合剂中的微细不溶性固体颗粒。表面活性剂可用作颜料分散剂。水性涂料的各组分和其制备方法进一步公开于聚合物、科学和工程简明大全,p 160-171(1990)中,这里作为参考引入。
非水性油墨和涂料用于水性漆料不适合的很多领域。例如,印在疏水性、无孔基材如金属、玻璃或塑料上的油墨必须快速干燥。因此,经常用溶剂如酮、酯、醇或烃代替水。这些溶剂基油墨在工业上广泛用于印制纸版箱和各种金属或塑料容器和部件的标签。具体的例子包括新油墨组合物和卷筒胶印光泽热定型油墨组合物。
还要求油墨和涂料在某些环境下是耐水的。在这些情况下,耐水性树脂可溶于油墨和涂料配料的非水溶剂中,以在干燥后提供所需的耐水性。这些非水性涂料的主要用途是用于金属和塑料汽车配件上。
本发明概述
本发明涉及一种包括已连接至少一个有机基团的碳的改性碳产品。该有机基团包括a)至少一个芳族基团或C1-C12烷基和b)至少一个离子基团、至少一个可电离基团、或离子基团与可电离基团的混合物。芳族基团或C1-C12烷基直接与碳原子连接,该有机基团的存在量为约0.10至约2.7μmol/m2或其量应使改性碳产品不容易分散于水中(正如本申请中定义的)。
本发明还涉及包括上述改性碳产品的水性或非水性涂料或油墨组合物。
本发明进一步涉及包括改性碳产品和非水性溶剂的非水性涂料或油墨组合物。改性碳产品包括已连接至少一个有机基团的碳,其中有机基团包括a)至少一个芳族基团或C1-C12烷基和b)至少一个离子基团、至少一个可电离的基团,或离子基团与可电离基团的混合物。芳族基团或C1-C12烷基直接与碳连接,而对于可存在的有机基团的数量并无限制。
这里使用的碳可为结晶或无定形类型。其例子包括但不限于石墨、炭黑、碳纤维、玻璃碳和活性炭(activated charcoal)或活性炭(activated carbon)。上述碳的微细形式是优选的;还可以使用不同碳的混合物。
优选实施方案的描述
本发明的改性碳产品包括已与其连接的至少一个有机基团的碳。此有机基团包括a)至少一个芳族基团或C1-C12烷基和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物。有机基团的芳族基团或C1-C12烷基直接与碳连接。此外,该有机基团的存在量为约0.10至约2.7μmol/m2或其量应使改性碳产品不容易分散于水中(正如本申请中定义的)。
这里使用的碳可为结晶或无定形类型。其例子包括但不限于石墨、炭黑、玻璃碳、活性炭(activated charcoal)、碳纤维、活性炭(activated carbon)和其混合物。上述碳的微细形式是优选的;还可以使用不同碳的混合物。
可通过碳与重氮盐在液体反应介质中反应使至少一个有机基团与碳连接,来制备改性碳产品。重氮盐可含有待与碳连接的有机基团。重氮盐为具有一个或多个重氮基团的有机化合物。优选的反应介质包括水、任何含水介质和任何含醇介质。水是最优选的介质。其中碳为炭黑的改性碳产品的例子和制备这些产品的各种优选方法描述于发明名称为“炭黑与重氮盐的反应、所得的炭黑产品及其用途”的US专利申请流水号no.08/356,660(申请日1995年12月15日)和其部分继续申请US专利申请流水号no.08/572,525(申请日1995年12月14日)中,这两份申请这里作为参考引入。其中碳不为炭黑的改性碳产品的例子和制备这些产品的各种优选方法描述于发明名称为“碳物质与重氮盐的反应产品和所得的碳产品”的US5,554,739、WO 96/18696和WO 96/18688中,所有这些文献这里都作为参考引入。
在上述改性碳产品的优选制备方法中,仅要求重氮盐足够稳定以使其与碳反应。因此,可用其它情况下认为是不稳定和要分解的一些重氮盐进行反应。一些分解过程将与碳和重氮盐之间的反应竞争并会降低与碳原子连接的有机基团的总数。此外,该反应可在许多重氮盐容易分解的高温下进行。高温还可有利地提高重氮盐在反应介质中的溶解性并改进其在工艺中的操作性。然而,高温会导致一些重氮盐因其它分解过程造成的损失。重氮盐可在现场制备。本发明的改性碳产品优选不含副产品或未连接的盐。
在优选的制备方法中,炭黑可与容易搅拌的稀含水淤浆形式的重氮盐反应,或在形成炭黑粒料的合适量的水存在下反应。若需要,炭黑珠粒可用常规造粒技术形成。其它碳可类似地与重氮盐反应。此外,例如当将采用除炭黑外的碳的改性碳产品用于非水性油墨和涂料中时,在优选的方法中碳优选应在与重氮盐反应前磨成细颗粒以防止改性碳产品在油墨和涂料中的不想要的沉淀。此外,当将采用除炭黑外的碳的改性碳产品用于喷墨油墨中时,在优选的方法中碳优选应在与重氮盐反应前磨成细颗粒以防止改性碳产品在油墨中的不想要的沉淀。当在碳上使用低含量的有机基团时必须在喷墨油墨中使用另一稳定颗粒的方式。其中一种方式可使用聚合物分散剂。
为本发明的一个实施方案的目的,与碳原子连接的有机基团的量对于后面将改性碳产品用于诸如涂料和油墨体系中是重要的。该量特别应低一些。换言之,有机基团的量可为约0.10至约2.7μmol/m2,优选约0.4至约2.5μmol/m2使用的碳,按碳的CTAB或t-面积计)。表征与碳原子连接形成改性碳产品的低含量的有机基团的另一方式是测量改性碳产品的残余物。具体地,这些残余值的测试为:首先将改性碳加入水溶液,如水中,然后将该含改性碳的水溶液通过325目筛子,并用水清洗直至滤液无色。可调节水的pH以增强碳上基团电离。对未通过筛子的改性碳称重。未通过筛子的重量百分比为残余值。对于本发明,具有残余值大于约5wt(重量)%的改性碳将认为不“容易分散于水中”。
一般认为与碳连接的有机基团的量越多,性能越好。然而,在某些情况下,与碳原子连接少量的有机基团获得更好的性能。例如当使用将本发明的改性碳产品用于非水领域如非水性油墨体系(包括非水性光泽油墨体系和非水性涂料配料)中时,可看到这些更好的性能。当本发明的改性碳产品用于这些体系和配料中时,获得改进的黑度(jetness)、浅蓝色和光泽,在某些情况下,还改进了油墨的流变性(通过Laray粘度测定)、平行板粘度测量值和垂直玻璃板流动性能。在某些油墨配料中,流动性比未处理的碳产品显著增加。
如上所述,有机基团包括芳族基团或C1-C12烷基。芳族基团包括但不限于含一个或多个环的不饱和环烃。芳族基团可为取代或未取代的。芳族基团包括芳基(例如苯基、萘基、蒽基等),和杂芳基(咪唑基、吡唑基、吡啶基、噻吩基、噻唑基、呋喃基、三嗪基、吲哚基等)。C1-C12烷基可为支化或未支化的,优选乙基。
可电离的基团为能够在使用的介质中形成离子基团的基团。离子基团可为阴离子基团或阳离子基团,可电离基团可形成阴离子或阳离子。
形成阴离子的可电离官能基团包括(例如)酸性基团或酸性基团的盐。因此,有机基团可包括衍生自有机酸的基团。当有机基团含形成阴离子的可电离基团时,该有机基团优选具有a)一个芳基或C1-C12烷基和b)至少一个具有pKa低于11的酸性基团,或至少一个具有pKa低于11的酸性基团的盐,或至少一个具有pKa低于11的酸性基团与至少一个具有pKa低于11的酸性基团的盐的混合物。酸性基团的pKa是指整个有机基团的pKa,而不只是酸性取代基。pKa更优选低于10,最优选低于9。芳族基团可为未取代的或可进一步被(例如)烷基取代。更优选地,有机基团为苯基或萘基,酸性基团为磺酸基、亚磺酸基、膦酸基或羧酸基。例子包括-COOH、-SO3H和-PO3H2、-SO2NHCOR和其盐,例如-COONa、-COOK、-COO-NR4 +、-SO3Na、-HPO3Na、-SO3NR4 +和PO3Na2,其中R为饱和或不饱和烷基或苯基。特别优选的可电离取代基为-COOH和-SO3H及其钠和钾盐。
因此,碳优选用含至少一个酸性官能团的芳基重氮盐处理。芳基重氮盐的例子包括,但不限于由对氨基苯磺酸、4-氨基苯甲酸、4-氨基水杨酸、7-氨基-4-羟基-2-萘磺酸、氨苯基硼酸、氨苯基膦酸和间氨基苯磺酸制备的那些重氮盐。
有机基团可为取代或未取代的磺苯基或其盐;取代或未取代的(多磺)苯基或其盐;取代或未取代的磺萘基或其盐;取代或未取代的(多磺)萘基或其盐;磺苯基的一个例子是羟磺苯基或其盐。
具有一个形成阴离子的可电离官能团的具体有机基团为对磺基苯基和4-羟基-3-磺苯基。
胺代表形成阳离子基团并可连接至与上述形成阴离子的可电离基团相同的有机基团上的可电离官能团。例如,氨可在酸性介质中质子化形成铵基。具有胺取代基的有机基团的pKb优选低于5。季铵基团(-NR3 +)和季鏻(-PR3 +)也代表阳离子基团的例子并可与上述形成阴离子的可电离基团相同的有机基团连接。有机基团优选含一个芳族基团,如苯基或萘基,和季铵或季鏻基团。季铵化环胺和季铵化的芳胺也可用作有机基团。
因此,N-取代的吡啶鎓化合物,如N-甲基-吡啶基可用于此。有机基团的例子包括但不限于3-C5H4N(C2H5)+X-,C6H4NC5H5 +X-,C6H4COCH2N(CH3)3 +X-,C6H4COCH2(NC5H5)+X-,3-C5H4N(CH3)+X-,C6H4N(CH3)3 +X-和C6H4CH2N(CH3)3 +X-,其中X为衍生自无机或有机酸的卤素或阴离子。
可存在于有机基团上的另一些非必要的官能团包括但不限于R、OR、COR、COOR、OCOR、卤素、CN、NR2、SO2NR(COR)、SO2NR2、NR(COR)、CONR2、NO2、SO3M、SO3NR4和N=NR′。R独立地表示氢、C1-C20取代或未取代烷基(支化或未支化的)、C3-C20取代或未取代链烯基、(C2-C4链烯氧基)xR″、或取代或未取代芳基。R′独立地为氢、C1-C20取代或未取代烷基(支化或未支化的)、或取代或未取代芳基。R″为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、C1-C20取代或未取代烷酰基或取代或未取代芳酰基。M为H、Li、Na、Cs或K。整数x为1-40,优选2-25。
有机基团的另一个例子是通式AyAr-的芳族基团,相当于通式AyArNH2的伯胺。在该通式中,变量具有如下含义:Ar为选自苯基、萘基、蒽基、菲基、联苯基、吡啶基和三嗪基的芳族基团。A为独立地选自上述官能团的芳族基团上的取代基,或A为未被取代或被一个或多个这些官能团取代的直链、支化或环烃基(优选含1至20个碳原子);当Ar为苯基时y为1至5的整数,当Ar为萘基时y为1至7的整数,当Ar为蒽基、菲基或联苯基时y为1至9的整数,当Ar吡啶基时y为1至4的整数,或当Ar为三嗪基时y为1至2的整数。当A为(C2-C4链烯氧基)xR″时,它优选为聚乙氧基化基团、聚丙氧基化基团或这两种基团的无规或嵌段混合物。
改性碳产品的另一个例子包括碳和连接的有机基团,该有机基团具有a)一个芳基或C1-C12烷基和b)至少一个通式SO2NR2或SO2NR(COR)的基团。R独立地为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、(C2-C4链烯氧基)xR′、或取代或未取代芳基。R′为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、C1-C20取代或未取代烷酰基或取代或未取代芳酰基;x为1至40。芳族基团包括对-C6H4SO2NH2、对-C6H4SO2NHC6H13、对-C6H4SO2NHCOCH3、对-C6H4SO2NHCOC5H11和对-C6H4SO2NHCOC6H5。
如上所述,上述改性碳产品可用于非水性油墨配料中。因此,本发明提供一种改进的含合适溶剂和已连接一个有机基团的改性碳产品,所述有机基团包括a)取代或未取代芳族基团或C1-C12烷基和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物。其它已知的油墨添加剂可加入油墨配料中。在本发明范围内还可使用含未改性碳产品和改性碳产品的混合物的油墨配料。
通常,油墨包括着色剂或颜料及调节粘度和干燥性的溶剂。油墨还可非必要地包括在印刷期间起到载体作用的漆料或清漆和/或改进印刷性能、干燥性等的添加剂。对于油墨性能、制备方法和用途的一般性讨论,参见印刷手册,第5版,R.H.Leach等人编著(Chapman & Hall,1993)。
本发明的改性碳产品可采用标准技术以预分散体或固体形式加入油墨配料中。使用本发明的改性碳产品可通过降低配料的粘度而具有显著的优点并节省费用。还可在配料中加入更多的碳产品。还可降低研磨时间。本发明的改性碳产品还可提供改进的黑色、蓝色调和光泽。
上述改性碳产品还可用于非水性涂料组合物如漆或面漆中。因此,本发明的一个优选实施方案是含合适溶剂和本发明的改性碳产品的涂料组合物。其它常规涂料添加剂可加入非水性涂料组合物如粘合剂中。
非水性涂料配料可根据最终用途的情况和需要在宽范围内变化。通常,涂料体系含至多30wt%的碳。树脂含量可在宽范围内变化,最多接近100%。例子包括丙烯酸、醇酸、氨基甲酸酯、环氧、纤维素等。溶剂含量可在0至80%内变化。例子包括芳烃,脂族烃,醇、多醇、酮、酯等。两类其它一般性添加剂为填料和改性剂。填料的例子为其它着色颜料(例如TiO2、酞青蓝等)、粘土、滑石、二氧化硅和碳酸盐。加入的填料量可高达60%,取决于最终要求。改性剂的例子为流平助剂和杀生物剂,其加入量通常低于5%。本发明的改性碳产品可用标准技术以预分散体或固体形式加入非水性涂料组合物中。
加入含本发明改性碳产品的组合物中的非水性介质包括但不限于三聚氰胺-丙烯酸酯树脂、三聚氰胺-醇酸树脂、氨基甲酸酯-硬化醇酸树脂、氨基甲酸酯-硬化丙烯酸酯树脂等。本发明的改性碳产品还可用于含水乳液漆料中。在这些类型的漆料中,具有一含颜料的非水性部分,其中该非水性部分分散于含水漆料中。因此本发明的改性碳产品可用作随后分散入含水乳液漆料中的非水性部分。
本发明的改性碳产品还可用于水性油墨和涂料配料中。水介质包括水与其它水混溶或水分散物质(如醇)的混合物。因此,本发明提供一种包括水和本发明的改性碳产品的水性油墨组合物。其它已知水性油墨添加剂可加入水性油墨配料中。如上所述,油墨可由上述各种组分组成。例如在US2,833,736、3,607,813、4,104,833、4,308,061、4,770,706和5,026,755中还公开了各种水性油墨组合物,这些文献这里都作为参考引入。
本发明的改性碳产品可用标准技术以预分散体或固体形式加入水性油墨配料中。
苯胺印刷油墨代表一类水性油墨组合物。水性油墨通常包括颜料、着色剂、粘合剂和溶剂。本发明的改性碳产品可用着水性油墨着色剂。本发明的改性碳产品用于水性报纸油墨中。例如,水性报纸油墨组合物包括水、本发明的改性碳产品、树脂和常规添加剂如消泡添加剂或表面活性剂。
本发明的改性碳产品还可用于水性涂料组合物如漆或面漆中。因此,本发明的一个实施方案是改进的含水涂料组合物,它包括水、树脂和本发明的改性碳产品。其它已知的含水涂料添加剂可加入水性涂料组合物中。例如,参见McGraw-Hill科技大全,第5版(McGraw-Hill,1982),这里作为参考引入。还可参见US5,051,466、5,319,044、5,204,404、5,051,464、4,692,481、5,356,973、5,314,945、5,266,406和5,266,361,所有这些文献这里都作为参考引入。本发明的水性组合物还可包括其它着色颜料(例如TiO2、酞青蓝等)、粘土、滑石、二氧化硅和碳酸盐。本发明的改性碳产品可用标准技术以预分散体或固体形式加入水性涂料组合物中。
油墨和涂料可用于各种领域,在本发明水性油墨和涂料中,改性碳产品的存在量低于或等于油墨或涂料的20%。在本发明范围内还可以使用未改性碳与本发明改性碳产品的混合物。下述常规添加剂可加入分散体中以进一步改进水性油墨或涂料的性能。
本发明的改性涂料还可用于其中油墨配料基于溶剂、水、或水乳液的喷墨油墨中。
此外,本发明还涉及其它非水性油墨和涂料配料。在这些配料中,合适的溶剂与本发明的改性碳产品一起存在。对于这些配料,改性碳产品包括已连接至少一个有机基团的碳,其中有机基团包括a)至少一个芳族基团或C1-C12烷基和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物。芳族基团直接与碳相连,存在于碳上的有机基团的量并无限制。对于非水性油墨和涂料配料,除了有机基团的量无上限或下限外,上述各种辅助添加剂组分以及各种组分的量同样无上限或下限。上面关于有机基团和其例子的讨论这里同样适合。
下面的实施例用于说明,而不是限制本发明的保护范围。
用ASTMD-4820获得BET氮表面积。用ASTMD-2414获得CATB面积。油墨和涂膜的光学性能用如下仪器测量:L*a*b*值用Hunter Scan6000(10°,D65 CIELAB色空间仪);光密度用Macbeth RD918密度计测量;光泽用BYK Gardner型号4527光泽测量仪测定。
氮和外表面积(t-面积)按照ASTM D-3037中描述的样品制备和测量步骤测定。在该测量中,氮气吸收等温线延伸至0.55相对压力。相对压力为压力(P)除以饱和压力(Po,氮气冷凝时的压力)。吸收层厚度(t,单位A)用如下关系式计算:
t=0.88(P/Po)2+6.45(P/Po)+2.98
然后将吸收的氮气体积(v)相对于t1作图,在t值点3.9与6.2A之间拟合一直线。t-面积由该直线的斜率按如下公式获得:
t-面积,m2/g=15.47×斜率
炭黑产品上的硫含量通过在对各样品进行Soxhlet洗涤后的燃烧分析测定。连接上的硫的mmol数通过与未处理的炭黑的分析结果测定相减而得到。
实施例1
用在现场生成的重
氮盐制备炭黑产品
将对氨基苯磺酸(3.0g)加入900mL去离子水中并将混合物加热至70-90℃。向该溶液中加入具有CTAB表面积350m2/g、t-面积366m2/g和DBPA120ml/100g的炭黑(100g)。将该混合物充分搅拌以使所有炭黑润湿。将1.2g亚硝酸钠在1.0mL去离子水中的溶液加入炭黑淤浆中。气体在数分钟内放出。将加热的混合物悬浮并将混合物在连续搅拌下冷却至室温。通过在70-100℃的烘箱中蒸发溶液使产品分离出来。该产品已连接对-C6H4-SO3Ha基团。
此外,该产品可通过在Buchner漏斗中过滤淤浆并用去离子水洗涤固体而分离。
实施例2
制备具有不同量的
连接基团的炭黑产品
用具有CTAB表面积350m2/g、t-面积366m2/g和DBPA120ml/100g的炭黑采用下表中所列的试剂量重复实施例1的步骤:
实施例 | 对氨基苯磺酸(g) | gNaNO2/g H2O | 炭黑(g) |
2a | 7.0 | 2.8/3 | 100 |
2b | 15.0 | 6.0/6 | 100 |
实施例3
用销钉式造粒机制备炭黑产品
将300g具有CTAB表面积350m2/g、t-面积366m2/g和DBPA 120ml/100g的炭黑和15g对氨基苯磺酸加入直径8英寸的销钉式造粒机中。将该造粒机在150rpm下旋转1分钟。加入去离子水(280mL)和亚硝酸钠(5.98g)的溶液并使造粒机在250rpm下转动2分钟。使造粒机停止转动,并取出转轴和销钉式,然后使造粒机在650rpm下再转动3分钟。在现场生成氢氧化4-磺基苯重氮盐内盐并使其与炭黑反应。将产品从造粒机中卸出,并在烘箱中在70-100℃下干燥。该产品已连接对-C6H4-SO3Na基团。对样品中的含硫量进行Soxhlet萃取分析,显示该产品具有0.15毫当量/g的连接磺酸根基团,或0.43μmol/m2的连接磺酸根基团。
实施例4
制备炭黑产品
按如下步骤制备4-氨基水杨酸的重氮盐溶液。向550mL去离子水中加入57.4g 4-氨基水杨酸。将该混合物在冰浴中冷却并加入93.75mL浓盐酸。向该冷却的混合物中加入25.9g亚硝酸钠在50mL去离子水中的溶液。该混合物颜色变黑并释放出一些气体。计算该溶液含0.038g 4-氨基水杨酸重氮盐/g溶液。
向在冰浴中冷却的具有CTAB表面积350m2/g和DBPA120ml/100g的炭黑(200g)在1.8L去离子水中的充分搅拌淤浆中加入233.2g 4-氨基水杨酸重氮盐溶液。释放出气体。连续搅拌直至不再观察到气体放出为止。将该淤浆真空过滤并用去离子水洗涤。将湿滤饼在烘箱中在75℃下干燥。产品已连接对-C6H3-(2-OH)-COOH基团。
实施例5
制备炭黑产品
向在冰浴中冷却的具有CTAB表面积350m2/g和DBPA120ml/100g的炭黑(200g)在1.8L去离子水中的充分搅拌淤浆中加入实施例4中制备的1168g 4-氨基水杨酸重氮盐溶液。释放出气体。连续搅拌直至不再观察到气体放出为止。将该淤浆真空过滤并用去离子水洗涤。将湿滤饼在烘箱中在75℃下干燥。产品已连接对-C6H3-(2-OH)-COOH基团。
实施例6
制备炭黑产品
按如下步骤制备4-氨基苯甲酸的重氮盐溶液。向925mL去离子水中加入89.1g 4-氨基苯甲酸。将该混合物在冰浴中冷却并加入162.5mL浓盐酸。加入丙酮(50mL)使4-氨基苯甲酸完全溶解。向该冷却混合物中加入44.9g亚硝酸钠在100mL去离子水中的溶液。向该冷却的混合物中加入44.9g亚硝酸钠在100mL去离子水中的溶液。该混合物颜色变黑并释放出一些气体。计算该溶液含0.061g 4-氨基苯甲酸重氮盐/g溶液。
向在冰浴中冷却的具有CTAM5表面积350m2/g和DBPA120ml/100g的炭黑(200g)在1.8L去离子水中的充分搅拌淤浆中加入131g 4-氨基苯甲酸重氮盐溶液。释放出气体。连续搅拌直至不再观察到气体放出为止。将该淤浆真空过滤并用去离子水洗涤。将湿滤饼在烘箱中在75℃下干燥。产品具有对-C6H4-COOH基团。该产品具有90%的325目残余物。
实施例7
制备具有不同量的
连接基团的炭黑产品
用实施例6中制备的重氮盐溶液,将具有CTAB表面积350m2/g和DBPA120mL/100g的炭黑采用不同量的苯基羧酸酯基团官能化。使用的量在下表中给出。使用的工艺与实施例6相似。
实施例 | 重氮盐溶液的量 | 炭黑的量 | 325目残余物 |
7a | 263g | 200g | 63.7% |
7b | 394g | 200g | 3.9% |
7c | 656g | 200g | 4.0% |
实施例8
在销钉式造粒机中制备炭黑产品
本方法与实施例3类似,但使用300g具有CTAB表面积350m2/g和DBPA120ml/100g的炭黑和24g 4-氨基苯甲酸。将该造粒机在500rpm下转动1分钟。加入去离子水(300mL)和亚硝酸钠(12.1g)的溶液并使造粒机在1100rpm下转动2-3分钟。将该产品从造粒机中卸出并在烘箱中在70-100℃干燥。该产品已连接对-C6H4-COONa基团。
实施例9
制备炭黑产品
本实施例代表生产类似于实施例6的产品的另一方法。将实施例8的产品(150g)在500mL去离子水中淤浆化。向该淤浆中加入21.9mL浓盐酸。搅拌30分钟后,将淤浆过滤并用去离子水洗涤,将该湿滤饼在75℃下干燥。该产品已连接对-C6H4-COONa基团。
实施例10
制备炭黑产品
本工艺与实施例1类似,但使用具有氮表面积560m2/g、DBPA 90mL/100g和挥发性含量9.5%的氧化炭黑。用于各处理程度的试剂的量在下表中给出。炭黑为在去离子水中的10%淤浆。
实施例 | 对氨基苯磺酸(g) | gNaNO2/gH2O | 炭黑(g) | mmol连接的S/g产品 |
10a | 6.0 | 2.4/3 | 200 | 0.162 |
10b | 10.0 | 4.0/5 | 200 | 0.237 |
10c | 20.0 | 8.0/8 | 200 | 0.496 |
10d | 30.0 | 12.0/12 | 200 | 0.670 |
10e | 50.0 | 19.9/20 | 200 | 1.00 |
实施例11
制备炭黑产品
使用实施例3的步骤,其中炭黑具有的t-面积为93m2/g和DBPA 55mL/100g。使用的试剂量在下表中给出。
来自实施例#的炭黑 | 炭黑(g) | 对氨基苯磺酸(g) | NaNO2(g) | 去离子水(mL) | mmol连接的S/g产品 | μmol连接的S/m2产品 |
11a | 400 | 0 | 0 | 215 | 0 | 0 |
11b | 400 | 4 | 1.6 | 215 | 0.041 | 0.44 |
11c | 400 | 8 | 3.2 | 215 | 0.084 | 0.90 |
11d | 400 | 20 | 8.0 | 215 | 0.193 | 2.08 |
这些产品已连接对-C6H4-COONa基团。对各样品进行Soxhlet萃取(乙醇)并分析硫含量。结果以及相应的连接量/m2在表中给出。
将本方法生产的粒料在8-英寸喷射磨(Sturtevant,Boston,MA)中研磨以将粒料转化为“飞扬”型产品。该方法描述于“Perry化学工程师手册”(第6版,R.H.Preey和D.Green编著,pp.8-46)中。这些研磨物质在实施例18中使用。
实施例12
制备炭黑产品
该方法描述在连续操作条件下制备炭黑产品。将100份/小时具有CTAB表面积350m2/g和DBPA 120mL/100g的炭黑与25份/小时对氨基苯磺酸和10份/小时亚硝酸钠水溶液投入连续操作的销钉式造粒机中。将所得物质干燥得到已连接对-C6H4SO3Na基团的炭黑产品。对样品进行Soxhlet萃取(乙醇)分析硫含量,显示产品具有0.95毫当量/g连接的磺酸根基团,或2.7μmol/m2连接的磺酸根基团。
实施例13
炭黑产品用于
涂料组合物中
本实施例说明在热固性丙烯酸组合物中使用炭黑产品。标准物为具有CTAB表面积350m2/g和DBPA 120mL/100g的炭黑(未进行任何额外处理)。这里评估的物质在实施例1、2a、2b和12中制备。
按如下方法制备涂料组合物,向各半加仑钢球磨中投入:2.1kg 1/4″钢球、3.3kg 1/2″钢球、282g研磨母料(64份ACRYLOID AT400树脂、30份正丁醇、6份甲基-正戊基酮)和30g炭黑。将球磨机罐在以82rpm运行的罐转动磨机(Paul O.Abbe mode 96806或等同设备)上在44rpm下转动给定时间。最终涂料配料通过首先用249g AT-400树脂中淡每一磨,然后在缸式球磨机上旋转1小时制备。第二次中淡通过加入304g 33份AT-400树脂、35.3份CYMEL 303三聚氰胺-甲醛树脂、7.2份甲基正戊基酮、8.5份乙酸2-乙氧基乙酯(乙酸溶纤剂-UnionCarbide)、1.8份CYCAT4040(苯磺酸和异丙醇的酸催化剂)、0.3份FLUORAD FC431添加剂、14份正丁醇的混合物,并旋转1小时进行。
ACRYLOID为购自Rohm and Haas,Philadelphia,PA的树脂的注册商标;CYMEL和CYCAT为购自CytecIndustries West Patterson,NJ的产品的注册商标;FLUORAD为购自3M,St,Paul,MN的添加剂的注册商标。光学性能通过在已空气干燥30分钟接着在250℃下烘烤30分钟的密封Leneta图纸上对3密耳薄膜进行光学性能测定。用Hunter色度计测量L*、a*和b*值。光密度用MacBeth RD918光密度计测量。光泽用BYK Gardner型号4527光泽计测量。粘度用在Brookfield KU-1粘度计上的Krebs Units中测量。
热固性丙烯酸配料根据描述的一般性方法通过在球磨机中研磨27小时制备。制备3密耳厚的刮涂膜并评估其光学性能。结果概列于下表中:
来自实施例#的炭黑 | 光密度 | L* | a* | b* | 光泽(60°) | 粘度 |
标准物 | 2.76 | 1.55 | 0.02 | 0.02 | 89.9 | 107 |
1 | 2.81 | 1.29 | -0.05 | -0.12 | 92.0 | 105 |
2a | 2.75 | 1.44 | 0.03 | -0.06 | 90.0 | 98 |
2b | 2.71 | 1.46 | -0.06 | 0.15 | 87.5 | 91 |
12 | 2.77 | 1.40 | 0.02 | 0.12 | 81.3 | 82 |
配料粘度随处理量增加而降低。所有光学性能在较低量时达到最大;用来自实施例1的炭黑产品(用3wt%对氨基苯磺酸重氮盐处理)生产的涂料与其它所有物质相比具有更大的光密度、更好的黑度、蓝色调和光泽。将这些样品进行重量补偿处理,即在各配料中炭黑的重量相同。
实施例14
用各种量的水杨酸官能化的炭黑产品
用于热固性丙烯酸涂料配料中
按照实施例13中的通常方法将实施例4和5中制备的产品经研磨18和42小时后在热固性丙烯酸配料中评估。结果概列于下表中。在本实施例中,将相同量的炭黑产品用于各配料中。标准物为具有CTAB表面积350m2/g和DBPA120mL/100g的炭黑(未进行任何额外处理)。
来自实施例#的炭黑 | 研磨时间(h) | 光密度 | L* | a* | b* | 光泽(60°) | 粘度 |
标准物 | 18 | 2.82 | 1.35 | -0.15 | 0.03 | 93.0 | 93 |
标准物 | 42 | 2.82 | 1.24 | -0.07 | -0.27 | 91.2 | 101 |
4 | 18 | 2.87 | 1.16 | -0.14 | -0.16 | 93.7 | 97 |
4 | 42 | 2.94 | 1.02 | -0.04 | -0.41 | 92.8 | 103 |
5 | 18 | 2.85 | 1.25 | -0.16 | -0.18 | 92.2 | 94 |
5 | 42 | 2.86 | 1.10 | 0.03 | -0.36 | 92.5 | 98 |
在各研磨时间下,来自实施例4的较低程度处理的物质与未处理的标准物或来自实施例5的更高程度处理的物质相比显示较大的光密度、黑度(L*)、更深的蓝色调和更好的光泽。
实施例15
用各种量的4-氨基苯甲酸处理的炭黑
产品用于热固性丙烯酸涂料组合物中
按照实施例13的描述将实施例6、7a和7b中制备的炭黑产品在热固性丙烯酸配料中评估。经27小时研磨后制备的涂料的光学性能在下表中给出。各配料含30g炭黑产品。标准物为具有CTAB表面积350m2/g和DBPA120mL/100g的炭黑(未进行任何额外处理)。
来自实施例#的炭黑 | 光密度 | L* | a* | b* | 光泽(60°) | 粘度 |
标准物** | 2.82 | 1.58 | -0.06 | 0.17 | 91.6 | 94 |
6 | 3.09 | 0.88 | -0.15 | -0.26 | 91.7 | 100 |
7a | 3.19 | 0.75 | -0.04 | -0.22 | 96.5 | 91 |
7b | 3.22 | 0.75 | -0.06 | -0.22 | 98.0 | 88 |
7c | 3.20 | 0.74 | -0.10 | -0.20 | 98.4 | 85 |
**经24小时研磨后制备的样品。
在本实施例中,来自实施例7a的用8wt%4-氨基苯甲酸重氮盐处理的具有连接的苯甲酸基团的炭黑与未处理的标准炭黑相比足以给出改进的光学性能。较高的处理量未显著改进涂料的性能。
实施例16
用各种量的对-氨基苯磺酸重氮盐进一步
官能化的表面处理的炭黑产品的性能
按实施例13的描述,在热固性丙烯酸配料中评估实施例10a-e(对氨基苯磺酸重氮盐分别为3、5、10、15、25wt%)中制备的炭黑产品。下表中给出27小时研磨后制备的涂料的光学性能。各配料含等量炭黑产品。标准物为具有氮表面积560m2/g和DBPA 90mL/100g和挥发物含量9.5%的表面处理炭黑。
来自实施例#的炭黑 | 光密度 | L* | a* | b* | 光泽(60°) | 粘度 |
标准物 | 2.68 | 1.74 | -0.07 | 0.11 | 88.8 | 92 |
10a | 2.95 | 1.32 | -0.01 | 0.14 | 93.7 | 89 |
10b | 2.88 | 1.12 | -0.11 | -0.19 | 86.5 | 98 |
10c | 2.84 | 1.21 | -0.08 | -0.10 | 76.9 | 102 |
10d | 2.85 | 1.24 | -0.07 | -0.06 | 84.0 | 99 |
10e | 2.81 | 1.34 | -0.03 | 0.08 | 90.0 | 97 |
具有连接的磺酸盐基团的氧化炭黑产品与未处理的标准物相比,具有更大的光密度、黑度和更蓝的色调。实施例10b(5wt%处理)比其它物质更黑且更蓝。
实施例17
用各种量的对氨基苯磺酸处理的炭黑产
品用于氨基甲酸酯硬化的丙烯酸配料中
本实施例说明炭黑产品在丙烯酸磁漆配料中的应用。将来自实施例3和12的炭黑产品用于如下组合物中。将这些炭黑产品在油漆搅拌器上的小钢磨(2-1/16″高x2-3/32″直径)中研磨。将200g 3/16"铬钢球、2.19g碳产品和19.9研磨漆料(由DMR-499丙烯酸混合磁漆(PPG罩面漆,Strongsville,OH)和二甲苯的80/20混合物组成)加入每一磨中。将该混合物研磨50分钟。将样品在赫格曼细度计上测定。通过将23.3g DMR-499、17.3g二甲苯和1.4g DXR-80氨基甲酸酯硬化剂(PPG罩面漆,Strongsville,OH)加入磨中并振摇15分钟,制备最终的配料。在密封的Leneta图纸上制备最终配料的3mil厚刮涂膜。将该涂膜空气干燥30分钟,在140°F下烘烤30分钟。按实施例13的描述测定光密度。
标准物为具有CTAB表面积350m2/g和DBPA120mL/100g的炭黑(未进行任何额外处理)。光密度和赫格曼细度在下表中给出。赫格曼值在赫格曼细度计上测定,其中使5个“砂子”颗粒聚集。
来自实施例#的炭黑 | 光密度 | L* | a* | b* | 光泽(60°) | 在50分钟时的赫格曼细度 |
标准物 | 2.83 | 1.23 | 0.08 | 0.05 | 52.3 | 4.0 |
3 | 3.08 | 0.70 | -0.04 | -0.27 | 88.0 | 6.6 |
12 | 2.79 | 1.41 | 0.17 | -0.03 | 92.5 | 6.2 |
在该配料中,通过极低光泽和赫格曼细度读数证实,标准物润湿不完全。来自实施例12的碳在重量上补偿对碳的处理量(2.66g)。实施例3的产品(5wt%对氨基苯磺酸重氮盐处理量)与标准物和更高程度的处理物质相比显示更好的光密度、黑度和蓝色调值。
实施例18
评估在光泽油墨
配料中的炭黑产品
将实施例11a-11d的炭黑产品在三辊磨上制备的标准热定形光泽油墨配料中评估。将11b-11d的性能与对比样品(实施例11a)比较。在三辊磨上通过将15g炭黑与35g研磨母料手工混合研磨制备炭黑样品。对样品按如下方式进行处理量重量补偿:11a,15.0g;11b 15.2g;11c,15.3g;11d,15.8g。该母料由9重量份LV-3427XL(热固着研磨漆料,LawterInternational,Northbrook,IL)和1份MAGIESOL 47油组成。将50g该混合物在70°F下转动的Kent三辊磨上研磨。将样品与等量的研磨母料混合进行配漆,然后涂于NIPRI生产的细度计G-2上评估细度。将标准物通常通过磨4次。若细度读数大于20μm,则再通过磨数次。将研磨后的物质与等量的配漆母料(3重量份LV3427XL、12份LV6025(热固着凝胶漆料、Lawter International)、5份MAGIESOL 47油)混合并将该混合物通过三辊磨一次,生产最终的油墨。
MAGIESOL为购自Magie Brothers,Franklin Park,IL的油的注册商标。
所得油墨的研磨细度数据和测量粘度在下表中给出。细度数据表中的值用μm表示(在G-2细度计上测量),并给出在细度计上检测到5个划痕/10个划痕/5个缺陷纹理时的值。钢棒Laray粘度按照ASTM方法D4040-91在25℃下用TMI 95-15-00 Laray粘度计测量(Testing Machines Inc.),垂直玻板流动性通过在竖立玻板之前使样品静置0、30和60分钟后0.5cc油墨样品向下垂直流过玻璃板的距离测量,平行板粘度性能用Toyoseiki平行板粘度计(Testing Machines Inc.)按照Japanese Industrial Standard,TestingMethods for Lithogarphic and Letterpress Inks(JIS K5701-4.1.2)中描述的方法测量。
性能/样品 | 11a | 11b | 11c | 11d |
炭黑性能 | ||||
油墨制剂研磨基础(5个划痕/10个划痕/砂子)三辊磨 | ||||
通过1次 | 6/0/46 | 0/0/27 | 0/0/24 | 0/0/24 |
通过2次 | 0/0/24 | 0/0/14 | 0/0/22 | 0/0/20 |
通过3次 | 0/0/20 | 0/0/13 | 0/0/12 | 0/0/17 |
通过4次 | 0/0/16 | 0/0/8 | 0/0/12 | 0/0/18 |
油墨性能钢棒Laray粘度 | ||||
粘度(在2500s-1时,泊) | 66.7 | 64.6 | 61.7 | 58.2 |
屈服值(在2.5s-1时,达因/cm) | 507 | 553 | 533 | 490 |
垂直玻板流动性能(mm) | ||||
未固着20分钟 85 125 105 11540分钟 95 155 132 14460分钟 105 175 145 167 | ||||
30分钟固着20分钟 43 98 85 9540分钟 56 126 109 11960分钟 61 145 126 139 | ||||
60分钟固着20分钟 26 95 79 8640分钟 42 125 102 11560分钟 48 143 120 135 | ||||
平行板粘度性能 | ||||
斜率(mm) | 8.6 | 9.8 | 9.3 | 9.2 |
截距(mm) | 23.9 | 23.3 | 24.9 | 25.6 |
屈服值(dye/cm2) | 128.4 | 113.3 | 116.0 | 114.1 |
这些数据说明处理是如何改进油墨配料的流变性的。在这些情况下,增加处理量会轻微降低Laray粘度,但显著升高流动性(垂直玻板流动性)。一小时固着后保持高流动性显示该油墨组合物随着时间流逝更均匀流动。这对于胶印油墨特别有价值。
平行板粘度斜率也是流动性的标志,但是在不同剪切条件下的流动性标志(较高的值相应于较大的流动性)。平行板粘度截距是样品塑性粘度的标志。
由炭黑产品11b-11d和标准炭黑(11a)制备的油墨的光学性能由使用RNA-42印刷性能试验仪(Research North America Inc.)印制的点测定并在下表中给出。由在薄膜厚度范围内印制的点的数据回归来计算1.0μm和2.0μm薄膜厚度的值。
由样品11a-d制备的1μm薄膜的光学性能
实施例 | OD | L* | a* | b* | 光泽60° |
11a | 1.47 | 19.9 | 1.94 | 5.87 | 45.3 |
11b | 1.37 | 23.23 | 1.93 | 6.18 | 45.1 |
11c | 1.38 | 23.67 | 1.79 | 5.72 | 42.3 |
11d | 1.20 | 31.10 | 1.63 | 5.84 | 38.6 |
由样品11a-d制备的2μm的光学性能
实施例 | OD | L* | a* | b* | 光泽60° |
11a | 2.28 | 2.93 | 0.68 | 0.75 | 49.1 |
11b | 2.24 | 3.16 | 0.94 | 1.33 | 46.8 |
11c | 2.08 | 5.41 | 1.53 | 2.67 | 48.1 |
11d | 2.10 | 4.30 | 0.95 | 1.39 | 39.7 |
这些数据显示增加处理量一定程度地降低光学性能。实施例11b综合了改进的流变性能(对于胶印油墨)和非常良好的分散性,同时具有最小的光学性能的损失。
实施例19
制备炭黑产品
使用实施例3的步骤,其中炭黑具有t-表面积93m2/g和DBPA 55mL/100g。使用的试剂量在下表中给出。
实施例# | 炭黑(g) | 对氨基苯甲酸(g) | NaNO2(g) | 去离子水(mL) |
19a19b19c19d | 400400400400 | 04820 | 02.014.0110.0 | 220220220220 |
这些产品已连接对-C6H4-CO2Na基团。
将由该方法生产的粒料干燥,然后用8英寸喷射磨(Sturtevant,Boston,MA)研磨使粒料转化为“飞扬性”产品。该方法描述于Perry化学工程师手册(第6版,R.H.Perry和D.Green编著,p8-46中)中,这里作为参考引入。这些研磨材料用于实施例20中。
实施例20
评估光泽油墨配料中的炭黑产品
将实施例19a-19d的炭黑产品在按实施例18所述的三辊磨上制备的标准热固着光泽油墨配料中进行评估。所有试验都按实施例18的描述进行。实施例19的炭黑产品为对比产品。按如下方式对样品进行处理量重量补偿:19a,15.0g;19b,15.2g;19c,15.3g;19d,15.8g。
所得油墨的研磨细度数据和粘度测量值在下表中给出。术语“回挂(hangback)”表示炭黑在第一次研磨期间不均匀分散于树脂中。
性能/样品 | 19 | 19 | 19 | 19 |
炭黑性能 | ||||
油墨制剂研磨基础(5个划痕/10个划痕/砂子)通过1次通过2次通过3次通过4次 | 10/6/466/4/345/0/260/0/20 | 回挂0/0/320/0/260/0/10 | 回挂0/0/300/0/12 | 回挂0/0/300/0/240/0/21 |
油墨粘度钢棒Laray粘度粘度(在2500s-1时,泊)屈服值(在2.5s-1时,dyne/cm) | 71.7832 | 71.8655 | 77.0715 | 75.5785 |
垂直玻板流动性能(mm)未固着20分钟40分钟60分钟30分钟固着20分钟40分钟60分钟60分钟固着20分钟40分钟60分钟 | 110133145781001156890102 | 105122130557078354349 | 125160179105137155100135150 | 1191511759412915092126146 |
平行板粘度性能斜率(mm)截距(mm)屈服值(dye/cm2) | 8.929.194.3 | 8.730.0107.9 | 9.028.6102.3 | 7.229.796.2 |
这些数据说明处理是如何改进油墨配料的流变性的。在这些情况下,增加处理量会显著增加流动性(垂直玻板流动性)。一小时固着后保持高流动性显示该油墨组合物随时间流逝更均匀流动。这对于胶印油墨特别有价值。此外,实施例19c的炭黑以比对比例19a更快的速率分散于油墨中。
平行板粘度斜率也是流动性的标志,但是在不同剪切条件下的流动性标志(更高的值对应于更大的流动性)。平行板粘度截流是样品塑性粘度的标志。
由对比炭黑19a和炭黑产品19b-19d制备的油墨的光学性能按实施例18中的描述进行测定。由在薄膜厚度范围内印制的点的回归数据计算1.0μm和2.0μm薄膜厚度的值。
由样品19a-d制备的1μm薄膜的光学性能
实施例 | OD | L* | a* | b* | 光泽60° |
19a19b19c19d | 1.401.541.341.17 | 24.519.5325.1628.40 | 1.181.811.801.32 | 3.675.385.714.32 | 36.741.942.731.4 |
由样品19a-d制备的2μm薄膜的光学性能
实施例 | OD | L* | a* | b* | 光泽60° |
19a19b19c19d | 2.142.252.131.85 | 5.123.474.899.37 | 0.830.751.321.21 | 1.530.922.422.85 | 44.849.842.131.7 |
这些数据显示增加处理量一定程度地降低光学性能。实施例19c具有改进的流变性能(用于胶印油墨)、非常良好的分散性,和可与对比例相比的光学性能。
实施例21
制备炭黑产品
在连续操作条件下制备具有不同量的连接基团的炭黑产品。将100份/小时炭黑(其t-面积为342m2/g、DBPA为106mL/100g)投入连续操作的销钉式造粒机中。各实施例中使用的对氨基苯磺酸、亚硝酸钠和水的量在下表中给出。将所得物质干燥得到具有连接的对-C6H4SO3Na基团的炭黑产品。连接的基团量通过Soxhlet萃取各产品样品分析硫含量测定。所得结果在下表中给出。
来自实施例#的碳 | 对氨基苯磺酸(份/小时) | NaNO2(份/小时) | 去离子水(份/小时) | mmol连接的S/g产品 | μmol连接的S/m2产品 |
21a21b21c21d21e | 357915 | 1.222.83.66.0 | 115115115115115 | 0.150.180.280.340.54 | 0.440.520.821.01.6 |
实施例22
将用各种量的对氨基苯磺酸处理的
炭黑用于氨基甲酸酯硬化的丙烯酸配料中
本实施例按照实施例17的描述进行。将来自实施例21a-e的炭黑产品用于组合物中。各实施例的研磨时间为60分钟。
来自实施例#的碳 | 光密度 | L* | a* | b* | 光泽(60°) | 研磨60分钟后的赫格曼细度 |
21a21b21c21d21e | 2.982.943.203.282.92 | 0.950.990.690.480.89 | -0.010.01-0.08-0.070.01 | -0.05-0.08-0.28-0.14-0.09 | 82.181.588.890.889.0 | 6.16.86.87.37.0 |
在该配料中,对于实施例21d的产品发现改进的光密度、黑度和光泽。具有更高或更低量的连接有机基团的碳产品并不改进涂料的颜色性能。
实施例23
制备炭黑产品
本方法描述在连续操作条件下制备炭黑产品。将100份/小时炭黑(其CTAB表面积为361m2/g、DBPA为117mL/100g)与9份/小时对氨基苯磺酸和3.8份/小时亚硝酸钠(以水溶液形式)投入连续操作的销钉式混合机中。将所得物质干燥得到已连接的对-C6H4SO3Na基团的颗粒状炭黑产品。对在Soxhlet萃取器中用90%乙醇萃取过夜的产品分析显示该产品具有0.35mmol/g连接磺酸盐基团,或0.97μmol/g连接磺酸盐基团。将该产品的样品用4英寸喷射磨在3磅/小时速率研磨,得到飞扬性物质。
实施例24
将炭黑产品用于涂料组合物中
本实施例说明将炭黑产品用于含另一颜料的热固性丙烯酸组合物中。标准炭黑为具有氮表面积560m2/g、DBPA 100mL/100g和挥发性含量9.5%的表面处理炭黑。这里评估的物质在实施例23中制备。
按如下方式制备涂料组合物:
组合物A:将15.1g炭黑、238.4g ACRYLOID AT400树脂、23.6g乙酸丁酯、23.6g乙二醇单单甲基醚乙酸酯和11.8g二甲苯投入1夸脱容器中,并用高速搅拌混合机在6000rpm下混合。将900g#550钢砂并在钢砂磨上研磨该混合物直至获得赫格曼细度7.5,制备研磨料。将564.4gACRYLOID AT400树脂、260g CYMEL 325三聚氰胺-甲醛树脂、27g乙酸丁酯、27g乙二醇单甲基醚乙酸酯和13.5g二甲苯在一加仑罐中辊磨4小时制备调和漆料。将研磨料(200份)和255份调和漆料用高速搅拌机在3000rpm下混合。
组合物B:将2kg 20mm陶瓷介质、204g ACRYLOID AT400树脂、356g DuPont R900 TiO2、16g乙酸丁酯、16g乙二醇单甲基醚和8g二甲苯投入半加仑陶瓷球磨机。将研磨缸在以82rpm操作的缸式辊磨机上研磨4小时使赫格曼细度达到7.5。再加入241g ACRYLOID AT400树脂、88.9gCYMEL 325三聚氰胺-甲醛树脂、18.3g乙酸丁酯、18.3g乙二醇单甲基醚乙酸酯和9.2g二甲苯,并将该混合物在球磨机上再辊磨4小时。
组合物C:将组合物A和组合物B的掺混物在油漆搅拌器上混合30分钟。
将组合物C的样品用6mil伯德涂抹器在玻璃板上制备刮涂膜,将该刮涂膜在室温下闪蒸5-10分钟.,并在100℃的烘箱中固化25分钟。测量L*、a*、b*值。从下表中可以看出,实施例23的颗粒状和飞扬性炭黑产品与对比炭黑相比呈现更大的着色力。当在制备组合物A中将所有碳产品研磨40分钟后,颗粒状物质获得类似结果,但飞扬性材料除外。
碳产品 | 组合物A份数 | 组合物B份数 | 组合物C中的炭黑% | 试验的样品 | L* | a* | b* |
对比例实施例23a实施例23a实施例23b | 202012.520 | 20202020 | 1.061.060.821.06 | 3213 | 50.2537.7644.3846.60 | -1.29-1.06-1.14-1.50 | -2.98-2.50-2.49-4.44 |
a=颗粒状
b=飞扬性
实施例25
制备炭黑产品
本方法描述在连续操作条件下制备炭黑产品。将100份/小时炭黑(其CTAB表面积为361m2/g、DBPA为117mL/100g)与对氨基苯磺酸和亚硝酸钠(以水溶液形式)投入连续操作的混合器中。将一部分所得物质干燥,得到已连接的对-C6H4SO3Na基团的炭黑产品。由分析已在Soxhlet萃取器中用甲醇萃取一夜的样品中的硫测定对-C6H4SO3Na基团的浓度。
实施例 | 份数/小时对氨基苯磺 | 份/小时NaNO2 | 份/小时水 | μmol连接的C6H4SO3Na/g | μmol连接的C6H4SO3Na/m2 | 325目残余物% |
25a25b25c25d25e | 25.420.11816.614.9 | 10.08.17.06.65.9 | 7575757575 | 1220940860800680 | 3.382.602.382.221.88 | 0.050.020.581.241.99 |
实施例26
炭黑产品用于涂料组合物中
本实施例说明实施例25的产品在水性热固性丙烯酸组合物中的用途。按如下方式制备涂料组合物:
组合物A:将水(57.8g)、0.1g Patco 845消泡剂和3.4g二甲基乙醇铵用低剪切混合器混合5分钟。加入Cargill 17-8241丙烯酸树脂(34.4g)和4.3g SURFYNOL CT136表面活性剂并将该混合物用低剪切混合器再混合10分钟。Patco 845消泡剂购自American Ingredients Co.,Kansas City,MO。Cargill 17-7241丙烯酸树脂购自Cargill,Inc.,Minneapolis,MN。SURFYNOLCT 136为Air Product and Chemical,Inc.,Allentown,PA.的注册商标。
组合物B:将水(68.5g)、23.0g Cargill 17-8241丙烯酸树脂、2.7g二甲基乙醇胺、5.4g Cargill 23-2347三聚氰胺树脂和0.3g BYK 306表面活性剂用低剪切混合器混合10分钟。Cargill23-2347三聚氰胺树脂购自Cargill,Inc.,Minneapolis,MN。BYK-306为BYK-Chemie USA,Wallingford生产并销售的表面活性剂的注册商标。
组合物C:将炭黑产品加入水中并在低剪切下搅拌约15分钟制备实施例25的炭黑产品的10wt%分散液。将组合物A(3.2g)加入该炭黑产品分散体中并用磁搅拌器混合15分钟。加入组合物B(19.3g)并将所得物质用磁搅拌棒再混合15分钟。将该涂料组合物在使用前静置过夜。
用3mil伯德涂膜器将涂料刮涂于在lenetta纸上并在163℃下干燥15分钟。下表给出当使用具有降低处理量的炭黑产品时获得的具有改进黑度的涂料。
来自实施例的碳 | μmol连接的C6H4SO3Na/m2 | L* | a* | b* |
25a25b25c25d25e | 3.382.602.382.221.88 | 1.811.551.301.161.19 | -0.16-0.020.030.04-0.03 | -0.030.010.020.06-0.03 |
本领域熟练技术人员通过理解这里公开的本发明说明书和实施方式,对于本发明的其它实施方案将是显而易见的。说明书和实施例仅认为是举例性的,本发明的真正范围和精神在后面的权利要求中给出。
Claims (43)
1.一种包括已连接至少一个有机基团的碳的改性碳产品,所述有机基团包括a)至少一个芳族基团或C1-C12烷基,和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物,其中有机基团的至少一个芳族基团或C1-C12烷基直接连接到碳上,且所述有机基团的存在量为约0.10至约2.7μmol/m2使用的碳,以碳的CTAB或t-面积计,或其存在量应使改性碳产品具有的残余值大于约5重量%。
2.权利要求1的组合物,其中有机基团的量为约0.4至约2.5μmol/m2使用的碳,以碳的CTAB或t-面积计。
3.权利要求1的组合物,其中离子或可电离基团为羧酸或其盐。
4.权利要求1的组合物,其中离子或可电离基团为磺酸或其盐。
5.权利要求1的组合物,其中有机基团为磺基苯基或其盐。
6.权利要求1的组合物,其中有机基团为对磺基苯基或其盐。
7.权利要求1的组合物,其中有机基团为对-C6H4SO3Na。
8.权利要求1的组合物,其中有机基团为羧基苯基或其盐。
9.权利要求1的组合物,其中有机基团为对羧基苯基或其盐。
10.权利要求1的组合物,其中有机基团为对-C6H4CO2H。
11.权利要求1的组合物,其中离子或可电离基团为季铵盐。
12.权利要求1的组合物,其中有机基团为3-C5H4N(C2H5)+X-,C6H4NC5H5 +X-,C6H4COCH2N(CH3)3 +X-,C6H4COCH2(NC5H5)+X-,3-C5H4N(CH3)+X-,C6H4N(CH3)3 +X-和C6H4CH2N(CH3)3 +X-,其中X为衍生自无机或有机酸的卤素或阴离子。
13.权利要求12的组合物,其中有机基团为C6H4NC5H5 +X-或C6H4CH2N(CH3)3 +X-。
14.权利要求1的组合物,其中有机基团为羧基-羟苯基或其盐。
15.权利要求1的组合物,其中有机基团为4-羧基-3-羟苯基。
16.权利要求1的组合物,其中碳为炭黑、石墨、碳纤维、玻璃碳、细分的碳、活性炭(activated charcoal)、活性炭黑(activated carbon)或其混合物。
17.权利要求16的组合物,其中碳为炭黑。
18.权利要求1的组合物,其中芳族基团的芳环为芳基。
18.权利要求1的组合物,其中芳族基团的芳环为芳基。
19.权利要求1的组合物,其中芳族基团的芳环为杂芳基。
20.权利要求1的组合物,其中有机基团为选自R、OR、COR、COOR、OCOR、卤素、CN、NR2、SO2NR(COR)、SO2NR2、NR(COR)、CONR2、NO2、SO3M、SO3NR4和N=NR′的一个或多个基团;其中R独立地为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、(C2-C4链烯氧基)xR″、或取代或未取代芳基;R′独立地为氢、C1-C20取代或未取代烷基、或取代或未取代芳基;R″为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、C1-C20取代或未取代烷酰基或取代或未取代芳酰基;M为H、Li、Na、Cs或K;X为1-40的整数。
21.权利要求1的组合物,其中改性碳产品进一步具有一通式AyAr-的芳族基团与改性碳产品连接,其中
Ar为选自苯基、萘基、蒽基、菲基、联苯基、吡啶基和三嗪基的芳族基团;
A为氢或选自R、OR、COR、COOR、OCOR、卤素、CN、NR2、SO2NR2、SO2NR(COR)、NR(COR)、CONR2、NO2、SO3M、SO3NR4和N=NR′的官能团,或A为未被取代或被一个或多个所述官能团取代的直链、支链或环烃基;
R独立地为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、(C2-C4链烯氧基)xR″、或取代或未取代芳基;
R′为氢、C1-C20取代或未取代烷基、或取代或未取代芳基;
R″为氢、C1-C20取代或未取代烷基、C3-C20取代或未取代链烯基、C1-C20取代或未取代烷酰基或取代或未取代芳酰基;x为1-40;
M为H、Li、Na、Cs或K;和
当Ar为苯基时y为1至5的整数,当Ar为萘基时y为1至7的整数,当Ar为蒽基、菲基或联苯基时y为1至9的整数,当Ar吡啶基时y为1至4的整数,或当Ar为三嗪基时y为1至2的整数。
22.一种非水性涂料组合物,包括非水溶剂和权利要求1的改性碳产品。
23.一种非水性油墨组合物,包括非水性漆料和权利要求1的改性碳产品。
24.一种水性涂料组合物,包括水和权利要求1的改性碳产品。
25.一种水性油墨组合物,包括水和权利要求1的改性碳产品。
26.一种非水性油墨或涂料组合物,包括改性碳产品和非水性溶剂或漆料,其中改性碳产品包括连接至少一个有机基团的碳,所述机基团包括a)至少一个芳族基团,和b)至少一个离子基团、至少一个可电离的基团、或离子基团与可电离基团的混合物,其中有机基团的至少一个芳族基团直接连接到碳上。
27.一种提高油墨流动性的方法,包括将权利要求1的改性碳产品加入油墨中,所述流动性通过玻板流动测量。
28.一种涂料组合物,包括水或非水溶剂、权利要求1的改性碳产品和除炭黑之外的着色颜料。
29.一种涂料组合物,包括水或非水溶剂、权利要求2的改性碳产品和除炭黑之外的着色颜料。
30.一种涂料组合物,包括水或非水溶剂、权利要求3的改性碳产品和除炭黑之外的着色颜料。
31.一种涂料组合物,包括水或非水溶剂、权利要求4的改性碳产品和除炭黑之外的着色颜料。
32.一种涂料组合物,包括水或非水溶剂、权利要求5的改性碳产品和除炭黑之外的着色颜料。
33.一种涂料组合物,包括水或非水溶剂、权利要求6的改性碳产品和除炭黑之外的着色颜料。
34.一种涂料组合物,包括水或非水溶剂、权利要求7的改性碳产品和除炭黑之外的着色颜料。
35.一种涂料组合物,包括水或非水溶剂、权利要求8的改性碳产品和除炭黑之外的着色颜料。
36.一种涂料组合物,包括水或非水溶剂、权利要求10的改性碳产品和除炭黑之外的着色颜料。
37.一种涂料组合物,包括水或非水溶剂、权利要求11的改性碳产品和除炭黑之外的着色颜料。
38.一种涂料组合物,包括水或非水溶剂、权利要求12的改性碳产品和除炭黑之外的着色颜料。和除炭黑之外的着色颜料。
40.一种涂料组合物,包括水或非水溶剂、权利要求20的改性碳产品和除炭黑之外的着色颜料。
41.一种涂料组合物,包括水或非水溶剂、权利要求21的改性碳产品和除炭黑之外的着色颜料。
42.权利要求26的涂料组合物,还包括除炭黑之外的着色颜料。
43.一种涂料组合物,包括水或非水溶剂、权利要求1的改性碳产品和粘土、滑石、二氧化硅或碳酸盐。
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US08/663,707 US5707432A (en) | 1996-06-14 | 1996-06-14 | Modified carbon products and inks and coatings containing modified carbon products |
US08/663,707 | 1997-01-14 |
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CN1227584A true CN1227584A (zh) | 1999-09-01 |
CN1108349C CN1108349C (zh) | 2003-05-14 |
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CN97197039A Expired - Lifetime CN1108349C (zh) | 1996-06-14 | 1997-06-11 | 用于油墨和涂料的改性碳产品含有其的组合物和其用途 |
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US (3) | US5707432A (zh) |
EP (1) | EP0910611B1 (zh) |
CN (1) | CN1108349C (zh) |
AR (2) | AR007604A1 (zh) |
AU (1) | AU726728B2 (zh) |
BR (1) | BR9710977A (zh) |
CA (1) | CA2258188C (zh) |
CO (2) | CO5021157A1 (zh) |
DE (1) | DE69707462T2 (zh) |
ES (1) | ES2165069T3 (zh) |
ID (1) | ID18342A (zh) |
IL (1) | IL127547A0 (zh) |
MX (1) | MX211243B (zh) |
MY (2) | MY117648A (zh) |
PH (2) | PH11997056948B1 (zh) |
TW (2) | TW371669B (zh) |
WO (1) | WO1997047692A1 (zh) |
ZA (2) | ZA975224B (zh) |
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1997
- 1997-01-14 US US08/783,411 patent/US5803959A/en not_active Expired - Lifetime
- 1997-06-11 IL IL12754797A patent/IL127547A0/xx not_active IP Right Cessation
- 1997-06-11 CA CA002258188A patent/CA2258188C/en not_active Expired - Lifetime
- 1997-06-11 DE DE69707462T patent/DE69707462T2/de not_active Expired - Lifetime
- 1997-06-11 WO PCT/US1997/010027 patent/WO1997047692A1/en active IP Right Grant
- 1997-06-11 EP EP97928937A patent/EP0910611B1/en not_active Expired - Lifetime
- 1997-06-11 CN CN97197039A patent/CN1108349C/zh not_active Expired - Lifetime
- 1997-06-11 AU AU33086/97A patent/AU726728B2/en not_active Ceased
- 1997-06-11 ES ES97928937T patent/ES2165069T3/es not_active Expired - Lifetime
- 1997-06-11 PH PH56948A patent/PH11997056948B1/en unknown
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- 1997-06-11 BR BR9710977-0A patent/BR9710977A/pt not_active IP Right Cessation
- 1997-06-12 ZA ZA9705224A patent/ZA975224B/xx unknown
- 1997-06-12 ZA ZA9705222A patent/ZA975222B/xx unknown
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- 1997-06-13 MY MYPI97002624A patent/MY117648A/en unknown
- 1997-06-13 MY MYPI97002628A patent/MY121268A/en unknown
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- 1997-06-13 TW TW086108216A patent/TW457285B/zh not_active IP Right Cessation
- 1997-06-16 CO CO97033302A patent/CO4990986A1/es unknown
- 1997-06-17 AR ARP970102642A patent/AR007604A1/es active IP Right Grant
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN100378180C (zh) * | 2001-04-27 | 2008-04-02 | 卡伯特公司 | 含有大t-面积碳制品的涂料组合物 |
CN1886472B (zh) * | 2003-09-30 | 2010-06-02 | 精工爱普生株式会社 | 油墨组合物 |
CN102558933B (zh) * | 2004-10-15 | 2014-12-17 | 卡伯特公司 | 高电阻率组合物 |
CN104151943A (zh) * | 2014-07-21 | 2014-11-19 | 深圳市墨库图文技术有限公司 | 一种接枝自分散炭黑分散液及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
MY121268A (en) | 2006-01-28 |
DE69707462D1 (de) | 2001-11-22 |
MY117648A (en) | 2004-07-31 |
CO4990986A1 (es) | 2000-12-26 |
BR9710977A (pt) | 2002-01-22 |
AR007604A1 (es) | 1999-11-10 |
DE69707462T2 (de) | 2002-06-06 |
EP0910611B1 (en) | 2001-10-17 |
CN1108349C (zh) | 2003-05-14 |
TW457285B (en) | 2001-10-01 |
ZA975222B (en) | 1998-01-14 |
ZA975224B (en) | 1998-01-05 |
US5707432A (en) | 1998-01-13 |
AR007605A1 (es) | 1999-11-10 |
TW371669B (en) | 1999-10-11 |
AU3308697A (en) | 1998-01-07 |
AU726728B2 (en) | 2000-11-16 |
MX211243B (en) | 2002-11-08 |
ID18342A (id) | 1998-04-02 |
EP0910611A1 (en) | 1999-04-28 |
PH11997056948B1 (en) | 2003-05-26 |
JP4001922B2 (ja) | 2007-10-31 |
US5885335A (en) | 1999-03-23 |
JP2000512329A (ja) | 2000-09-19 |
CA2258188C (en) | 2006-10-24 |
US5803959A (en) | 1998-09-08 |
CO5021157A1 (es) | 2001-03-27 |
WO1997047692A1 (en) | 1997-12-18 |
CA2258188A1 (en) | 1997-12-18 |
ES2165069T3 (es) | 2002-03-01 |
IL127547A0 (en) | 1999-10-28 |
PH11997056964B1 (en) | 2000-03-24 |
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