CN1130430C - 用于油墨和涂料的具有离去基团的改性碳产品和其组合物 - Google Patents
用于油墨和涂料的具有离去基团的改性碳产品和其组合物 Download PDFInfo
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- CN1130430C CN1130430C CN98810037A CN98810037A CN1130430C CN 1130430 C CN1130430 C CN 1130430C CN 98810037 A CN98810037 A CN 98810037A CN 98810037 A CN98810037 A CN 98810037A CN 1130430 C CN1130430 C CN 1130430C
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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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/44—Carbon
- C09C1/48—Carbon black
- C09C1/56—Treatment of carbon black ; Purification
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- 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
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
- D01F11/10—Chemical after-treatment of artificial filaments or the like during manufacture of carbon
- D01F11/14—Chemical after-treatment of artificial filaments or the like during manufacture of carbon with organic compounds, e.g. macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
Abstract
公开了改性碳产品,它包括已连接至少一个有机基团的碳,其中所述有机基团包括a)至少一个芳族基团或C1-C12烷基,和b)具有式-AG-Sp-LG-Z的离子或可电离的基团,其中AG是活化基团,Sp是有助于活化基团促进离去基团除去效果的间隔基,LG是离去基团,且Z是抗衡离子,其中芳族基团或C1-C12烷基直接连接到碳上,且有机基团可以任何量存在。还公开了一种含改性碳产品的油墨和涂料。
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。
目前所用的有很多种类的油墨。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.7p.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,其中该有机基团包括a)至少一个芳族基团或C1-C12烷基和b)具有式-AG-Sp-LG-Z的基团,其中AG是活化基团,Sp是有助于活化基团促进离去基团除去效果的间隔基。LG是离去基团,且Z是抗衡离子。芳基或C1-C12烷基直接与碳连接。本发明还涉及包括上述改性碳产品的涂料或油墨组合物。
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连接至少一个有机基团的碳,其中该有机基团包括a)至少一个芳族基团或C1-C12烷基和b)具有式-AG-Sp-LG-Z的基团,其中AG是活化基团,Sp是有助于活化基团促进离去基团除去效果的间隔基。LG是离去基团,且Z是抗衡离子。活化基团可为促进离去基团除去的任何基团。活化基团的例子包括但不限于:-SO2-,-NRSO2-,-NRCO-,-O2C-,-SO2NR等。R独立地为氢、C1-C12取代或未取代烷基,C2-C12取代或未取代链烯基、氰乙基、或取代或未取代的C7-C20芳烷基或烷芳基。间隔基优选是在邻近-AG的碳上具有至少一个氢的任意亚乙基或取代的亚乙基。该离去基团是可以从连接到碳着色剂或颜料上的有机基团上除去的任意基团。离去基团从连接到碳产品的有机基团除去后,减少了仍连在碳产品上的离子基团或可电离的基团的数目。离去基团的例子包括但不限于:-OSO3-,-SSO3 -,-OPO3 2-,Q+等。Q+是NR3 +,N(C2H4)3N+或N-取代的杂环,如吡啶鎓。芳族基团或C1-C12烷基直接与碳连接且对在碳上存在的有机基团的量没有限制。优选在碳上该有机基团的存在量为约0.10至约4.0μmol/m2,更优选为约2.0至3.3μmol/m2,以碳的CTAB或t-面积计。适宜的式-AG-Sp-LG-Z的离子或可电离的基团包括但不限于:
SO2C2H4OSO3 -M+,SO2C2H4SSO3 -M+,
SO2C2H4OPO3 2-M2 +,SO2C2H4Q+X-,NRSO2C2H4OSO3 -M+,NRSO2C2H4SSO3 -M+,
NRSO2C2H4OPO3 2-M2 +,NRSO2C2H4Q+X-,SO2NRC2H4OSO3 -M+,SO2NRC2H4SSO3 -M+
,SO2NRC2H4OPO3 2-M2 +,SO2NRC2H4Q+X-,NRCOC2H4OSO3 -M+,
NRCOC2H4S-SO3 -M+,NRCOC2H4Q+X-,O2CC2H4OSO3 -M+,O2CC2H4SSO3 -M+,
SO2C2H4SO2C6H4SO3 -M+,SO2C2H4SO2C6H4CO2 -M+,NRCOC2H4SO2C2H4OSO3 -M+,
NRCOC2H4SO2C6H4SO3 -M+,NRCOC2H4SO2C6H4CO2 -M+,其中R独立地为氢、C1-C12取代或未取代烷基,C2-C12取代或未取代链烯基、氰乙基、或C7-C20取代或未取代芳烷基或烷芳基;M是H,或碱金属离子,如Li,Na,K,Cs,或Rb,以及Q如上定义。X是卤离子或衍生于矿物酸或有机酸的阴离子。
也可使用通常所述和上面特别提及的杂环和环状离子或可电离的基团,如N-取代的杂环。特定的例子包括但不限于:在上述的N-环式中,SO3 -是LG,M+是抗衡离子。AG-Sp是N-环。环的例子包括:其中R定义如上,且“波浪”线表示连接到有机基团,如芳香基。更具体的例子为:其中直线代表连接到碳产品上。在高温或碱性条件下,这些环型结构可释放出亚硫酸根离子。
优选的有机基团是C6H4SO2C2H4OSO3 -Na+。当把碳产品例如置于含水油墨或涂料制剂中时,该离子或可电离的基团的LG-Z优选通过消除反应从碳产品上除去。消除反应在一般时间在加热或不加热下进行。这种消除反应的例子是SO2C2H4OSO3M+与(CH3)2NC2H4OH反应形成SO2CH2=CH2基团和M+H(CH3)2N+C2H4OHSO4 2-。可制备含有一种或多种这些改性碳产品和适宜有机溶剂或水性介质如水的水性或非水性油墨和涂料组合物或制剂。当这些改性碳产品含在涂料制剂中且发生了消除反应时,改性碳产品包括连接上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)具有式-AG-CH=CH2,-AG-C2H4OH或-AG-C2H4-O-C2H4-AG-的基团,其中每个AG可相同或不同并连接到碳上。含有这些改性碳产品的油墨和涂料也可是本发明的一部分。
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。
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。
其它另外的有机基团也可连接到本发明的碳产品上。这些另外的有机基团包括a)至少一个芳族基团或C1-C12烷基和b)离子基团或可电离的基团,其中该离子基团或可电离基团不从有机基团除去。优选这些另外的但为任选的离子或可电离的基团的浓度低于2.4μmol/m2。这些可电离的基团在使用介质时能形成离子基团。离子基团可为阴离子或阳离子,可电离基团可形成阴离子或阳离子。可以连接的其它另外的有机基团的例子包括但不限于:例如,C6H4SO3 -Na+和C6H4CO2 -Na+。其它例子介绍于U.S专利5,571,311和5,630,868中和同时待审的U.S申请08/572,542,08/663,707,08/663,694中,所有这些文献全文引入作为参考。
本发明改性碳产物的分散液在加入稳定剂或缓冲剂如苯甲酸钠或乙酸钠下对过早的消除或水解是稳定的。这些稳定剂或缓冲剂在水溶液中通常以提高这些分散液的稳定性的量而存在,并优选低于约0.05M。除了式-AG-Sp-LG-Z外还含有连接的羧酸根的碳产品可具有改进的稳定性。
本发明的改性碳产品可用于水性和非水性油墨和涂料配料中。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)。其它已知的油墨添加剂可加入到油墨配料中。使用未改性碳产品和改性碳产品的混合物也在本发明的范围内。
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也可用于喷墨油墨配料中。在U.S专利5,571,311和5,630,868中所述的添加剂和配料可与本发明的改性碳产品一起使用。
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、酞菁蓝等)、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。
下面的实施例用于说明,而不是限制本发明的保护范围。
用ASTM D-4820获得BET氮表面积。用ASTM D-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)。
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,单位埃)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t作图,在t值点3.9与6.2埃之间拟合一直线。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
制备炭黑产品
该实施例介绍制备称为A-J的炭黑产品。对于每一个样品,将具有CTAB表面积361m2/g和DBPA 117ml/100g的炭黑10g加入到对氨基苯磺酸和4-氨基苯基硫酸根合乙基砜(APSES)(其量如下表所示)在约90g水中的在约70℃下搅拌的溶液中。将亚硝酸钠在数mL水中的溶液在一分钟内加入,并将混合物在70℃下搅拌1小时。生成的分散液含有具有已连接C6H4-SO3 -Na+和/或C6H4SO2C2H4OSO3 -Na+基团的炭黑产品。
实施例 | 对氨基苯磺酸,g | APSES,g | NaNO2,g |
A | 0.61 | 1.49 | 0.61 |
B | 0.00 | 4.08 | 1.01 |
C | 1.30 | 0.90 | 0.74 |
D | 1.75 | 1.24 | 1.00 |
E | 0.87 | 2.14 | 0.87 |
F | 1.96 | 0.37 | 0.87 |
G | 1.37 | 0.25 | 0.61 |
H | 0.00 | 3.00 | 0.74 |
I | 1.85 | 0.00 | 0.74 |
J | 2.50 | 0.00 | 1.00 |
实施例2
制备炭黑产品
将300g具有CTAB表面积350m2/g和DBPA 120ml/100g的炭黑和对氨基苯磺酸(SA)和4-氨基苯基硫酸根合乙基砜(APSES)(其量如下表所示)加入直径8英寸的销钉式造粒机中。将该造粒机在100rpm下旋转1分钟。在65℃下加入去离子水和亚硝酸钠的溶液并使造粒机在600rpm下转动1分钟。加入另外5g水并在600rpm下再转动1分钟。在现场生成氢氧化4-磺基苯重氮盐内盐和/或氢氧化4-(2-硫酸根合乙基)磺基苯重氮盐内盐并使其与炭黑反应。产品已连接有对-C6H4SO3 -Na+和/或对-C6H4SO2C2H4OSO3 -Na+基团。把选择的样品在0.5M氢氧化钠中煮沸1小时并用水在Soxhlet萃取仪中萃取过夜、干燥并分析其含硫量来确定连接的砜的量。
实施例 | SA,g | APSES,g | NaNO2,g | H2O,g | 总处理量,μmol/m2 | 连上的砜μmol/m2 |
2A | 0 | 122 | 31.0 | 253 | 4.14 | 3.26 |
2B | 0 | 106 | 26.9 | 253 | 3.60 | 2.88 |
2C | 0 | 90.2 | 22.8 | 253 | 3.06 | 2.69 |
2D | 26.5 | 63.7 | 26.9 | 229 | 3.62 | - |
2E | 24.1 | 57.8 | 22.8 | 253 | 3.29 | - |
实施例3
制备炭黑产品
将300g具有CTAB表面积350m2/g和DBPA 120ml/100g的炭黑和66.1g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100rpm下旋转1分钟。在65℃下加入去离子水(228.5g)和亚硝酸钠(26.9g)的溶液并使造粒机在600rpm下转动1分钟。加入另外5g水并在600rpm下再转动1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。干燥样品并用甲醇在Soxhlet萃取仪中萃取过夜、干燥并分析其含硫量。该产品已连接有对-C6H4SO3 -Na+基团。
实施例4
制备炭黑产品
将100份/小时具有CTAB表面积361m2/g和DBPA 117mL/100g的炭黑与对氨基苯磺酸和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。
实施例 | 对氨基苯磺酸,份/小时 | NaNO2,份/小时 |
4A | 25 | 10 |
4B | 18 | 7.2 |
实施例5
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实施例1中的炭黑产品。按如下方法制备涂料组合物:
组合物A:把水(289g),0.5g Patco 845消泡剂和17g二甲基乙醇胺使用低剪切混合器混合5分钟。加入Cargill 17-7241丙烯酸酯树脂(172g)和21.5gSURFYNOL CT136表面活性剂并把该组合物用低剪切混合器混合10分钟。Patco 845消泡剂购自于American Ingredients Co.,Kansas City,MO。Cargill 17-4271丙烯酸酯树脂购自于Cargill Inc.,Minneapolis,MN。SURFYNOL CT 136是Air Products and Chemicals,Inc.,Allentown,PA的注册商标。
组合物B:把水(61.0g),84.4g Cargill 17-7241丙烯酸酯树脂,10.1g二甲基乙醇胺,19.8g Cargill 23-2347蜜胺树脂和1.14g BYK-306表面活性剂使用低剪切混合器混合10分钟。Cargill 23-2347蜜胺树脂购自于Cargill Inc.,Minneapolis,MN。BYK-306是BYK-Chemie USA,Wallingford制造并销售的表面活性剂的注册商标。
组合物C:如下制备实施例1的炭黑产品的2%重量的分散液:把该炭黑加入到水中并在低剪切下搅拌约15分钟。这种分散液(12.5g)与3.2g组合物A和9.3g组合物B用磁力棒搅拌约20分钟。让涂料组合物在使用前静止的指定的时间。
用具有氮表面积560m2/g和DBPA 100ml/100g以及挥发物含量为9.5%的炭黑制备对照涂料组合物。把组合物A(28.2g),19.4g水,2.6g炭黑和155g#550钢珠在油漆振荡器的1/2品脱罐中振荡3小时。过滤后,把这种材料加入到19.3g组合物B中并把该混合物用用磁力棒搅拌约15分钟。让涂料组合物在使用前静止的指定的时间。
用3密尔Bird涂布仪把涂料涂在Leneta纸上并在163℃下干燥15分钟。涂布透明涂层并再次干燥样品。测定L*、a*和b*值并与对照炭黑相比较。下表表明:当使用具有连上对-C6H4SO2C2H4OSO3 -Na+基团的炭黑产品时,得到具有改善黑度的涂层。
来自实施例的炭黑 | 时间(天) | ΔL* | Δa* | Δb* |
A | 9 | -0.51 | 0.10 | -0.09 |
B | 9 | -0.29 | 0.07 | 0.26 |
C# | 7 | -0.23 | 0.02 | 0.21 |
D## | 7 | 0.04 | -0.02 | 0.08 |
D## | 9 | -0.16 | 0.09 | -0.12 |
E | 7 | -0.41 | 0.02 | 0.14 |
F | 7 | 0.08 | -0.07 | 0.11 |
F | 9 | -0.03 | 0.19 | -0.18 |
G | 7 | -0.32 | -0.02 | 0.10 |
H | 7 | -0.24 | 0.23 | 0.22 |
I | 7 | 0.21 | 0.09 | 0.20 |
J | 7 | 0.07 | -0.15 | 0.16 |
#为三次实验的平均值
##为二次实验的平均值
实施例6
炭黑产品用于
涂料组合物中
本实施例说明在实施例5的水性涂料组合物中使用实施例1B中的炭黑产品。如实施例5制备和评估涂料,除了在不同时间涂布和用和不用透明涂料来评估外。其结果表明:当让该液体涂料制剂在使用前静止一段时间时,改善了涂料的黑度。
有透明涂层 | 无透明涂层 | |||||
时间 | ΔL* | Δa* | Δb* | ΔL* | Δa* | Δb* |
1小时21小时3天7天9天 | 0.340.01-0.28-0.40-0.29 | 0.190.15-0.060.000.07 | 0.400.270.170.040.26 | 0.360.14-0.31-0.20-0.24 | 0.300.150.080.210.05 | 0.340.260.260.320.47 |
实施例7
炭黑产品用于
涂料组合物中
本实施例说明在水溶性热固性丙烯酸组合物中使用实施例2-4中的炭黑产品。按如下方法制备涂料组合物:
组合物A:把水(289.2g),0.4g Patco 845消泡剂和17g二甲基乙醇胺使用低剪切混合器混合5分钟。加入Cargill 17-7241丙烯酸酯树脂(86.0g)和10.7g SURFYNOL CT136表面活性剂并把该组合物用低剪切混合器混合10分钟。
组合物B:把水(685.5g),230.2g Cargill 17-7241丙烯酸酯树脂,27.4g二甲基乙醇胺,54.0份Cargill 23-2347蜜胺树脂和3.0份BYK-306表面活性剂使用低剪切混合器混合10分钟。
组合物C:如下制备实施例2B的炭黑产品的10%重量的分散液:把该炭黑加入到水中并在低剪切下搅拌约15分钟。这种分散液(2.5g)与3.2g组合物A和19.3g组合物B用磁力棒搅拌约20分钟。让涂料组合物在使用前静止的指定的时间。
用实施例5的方法评估涂料并与对照炭黑相比较。下表表明:当使用具有连上C6H4SO2C2H4OSO3 -Na+基团的实施例炭黑产品时,得到具有改善黑度的涂层。
来自实施例的炭黑 | 时间天 | SA处理量,μmol/m2 | APSES处理量,μmol/m2 | 总处理量,μmol/m2 | ΔL* | Δa* | Δb* |
2A | 5 | 0 | 4.14 | 4.14 | -0.40 | 0.12 | 0.18 |
2B | 2 | 0 | 3.60 | 3.60 | -0.61 | 0.05 | 0.03 |
2B | 5 | 0 | 3.60 | 3.60 | -0.61 | 0.12 | 0.05 |
2C | 5 | 0 | 3.06 | 3.06 | -0.47 | 0.02 | 0.07 |
2D | 5 | 1.46 | 2.16 | 3.62 | -0.32 | 0.05 | 0.14 |
2E | 5 | 1.33 | 1.96 | 3.29 | -0.44 | -0.07 | 0.17 |
3 | 5 | 3.63 | 0 | 3.63 | 0.27 | -0.02 | 0.10 |
4A | 5 | 4.14 | 0 | 4.14 | 0.30 | -0.06 | 0.14 |
4B | 5 | 2.97 | 0 | 2.97 | 0.02 | 0.186 | -0.01 |
实施例8
炭黑产品用于
涂料组合物中
本实施例说明在类似于实施例5的水性涂料组合物中使用实施例2B中的炭黑产品。按如下方法制备涂料组合物:
组合物A:把水(57.8g),0.1g Patco 845消泡剂和胺使用低剪切混合器混合5分钟。加入Cargill 17-7241丙烯酸酯树脂(34.4g)和4.3g SURFYNOLCT136表面活性剂并把该组合物用低剪切混合器混合另外10分钟。
组合物B:把水(342.7g),115.1g Cargill 17-7241丙烯酸酯树脂,胺,27.0gCargill 23-2347蜜胺树脂和1.5g BYK-306表面活性剂使用低剪切混合器混合10分钟。
组合物C:如下制备实施例2B的炭黑产品的10%重量的分散液:把该炭黑加入到水中并在低剪切下搅拌约15分钟。这种分散液(2.5g)与3.2g组合物A和19.3g组合物B用磁力棒搅拌约20分钟。让涂料组合物在使用前静止的指定的时间。
用实施例5的方法评估涂料并与实施例5的对照炭黑相比较。
胺 | 用于组合物A的胺重量,g | 用于组合物B的胺重量,g | 时间小时 | ΔL* | Δa* | Δb* |
三乙基胺 | 3.9 | 15.5 | 1 | -0.05 | 0.06 | -0.05 |
三乙基胺 | 3.9 | 15.5 | 120 | -0.28 | 0.17 | 0.15 |
2-氨基-2-甲基丙醇 | 3.4 | 13.7 | 1 | 0.82 | 0.38 | 0.82 |
2-氨基-2-甲基丙醇 | 3.4 | 13.7 | 120 | -0.07 | 0.05 | 0.24 |
实施例9
制备炭黑产品
将100份/小时具有CTAB表面积361m2/g和DBPA 117mL/100g的炭黑与35份/小时对氨基苯基硫酸根合乙基砜和100.4份/小时亚硝酸钠的9%水溶液投入连续操作的销钉式造粒机中。所得物质连上C6H4SO2C2H4OSO3 -Na+基团。
实施例10
炭黑产品用于
涂料组合物中
本实施例说明在实施例5的水性涂料组合物中使用实施例9中的炭黑产品。制备涂料并在8天后如实施例5加以评估。涂料的ΔL*、Δa*、Δb*值分别为-0.43,0.00和0.15。
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 (44)
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)具有式-AG-Sp-LG-Z的离子或可电离的基团,其中AG是活化基团,Sp是帮助活化基团以促进LG的除去的间隔基,LG是离去基团,且Z是抗衡离子,其中芳族基团或C1-C12烷基直接连接到碳上。
2.权利要求1的改性碳产品,其中所说的离子或可电离基团为
SO2C2H4OSO3 -M+,SO2C2H4SSO3 -M+,SO2C2H4OPO3 2-M2 +,
SO2C2H4Q+X-,NRSO2C2H4OSO3 -M+,NRSO2C2H4SSO3 -M+,NRSO2C2H4OPO3 2-M2 +,
NRSO2C2H4Q+X-,SO2NRC2H4OSO3 -M+,SO2NRC2H4SSO3 -M+,SO2NRC2H4OPO3 2-M2 +,
SO2NRC2H4Q+X-,NRCOC2H4OSO3 -M+,NRCOC2H4SSO3 -M+,NRCOC2H4Q+X-
,O2CC2H4OSO3 -M+,O2CC2H4SSO3 -M+,SO2C2H4SO2C6H4SO3 -M+,
SO2C2H4SO2C6H4CO2 -M+,NRCOC2H4SO2C2H4OSO3 -M+,NRCOC2H4SO2C6H4SO3 -M+
,NRCOC2H4SO2C6H4CO2 -M+其中R独立地为氢、C1-C12取代或未取代烷基,C2-C12取代或未取代链烯基、氰乙基、或C7-C20取代或未取代芳烷基或烷芳基;M是H,Li,Na,K或Cs,以及Q+是NR3 +,N(C2H4)3N+或N-取代的杂环,X是卤离子或衍生于矿物酸或有机酸的阴离子。
3.权利要求2的改性碳产品,其中所说的离子或可电离基团为SO2C2H4OSO3 -M+。
4.权利要求1的改性碳产品,其中所说的活化基团为-SO2,-NRSO2,-NRCO,-O2C或-SO2NH。
5.权利要求1的改性碳产品,其中该间隔基是亚乙基或取代的亚乙基。
6.权利要求5的改性碳产品,其中所说的间隔基是在邻近-AG的碳上具有至少一个氢的基团。
7.权利要求1的改性碳产品,其中所说的离去基团为-OSO3 -,-SSO3 -,-OPO3 2-或Q+,而Q+是NR3 +,N(C3H4)3N+或N-取代的杂环,其中R独立地为氢、C1-C12取代或未取代烷基,C2-C12取代或未取代链烯基、氰乙基、或C7-C20取代或未取代芳烷基或烷芳基。
8.权利要求1的改性碳产品,其中所说的抗衡离子是H,Li,Na,K,Rb,Cs,或卤离子或衍生于矿物酸或有机酸的阴离子。
9.权利要求1的改性碳产品,其中所说的碳为炭黑、石墨、碳纤维、玻璃碳、细分的碳、活性炭或其混合物。
10.权利要求1的改性碳产品,其中碳为炭黑。
11.权利要求1的改性碳产品,还包括连接到所说碳上的第二有机基团,其是所说的第二有机基团包括a)一个芳族基团或C1-C12烷基和b)离子基团或可电离的基团,其中该离子基团或可电离基团不从有机基团除去。
12.权利要求11的改性碳产品,其中所说的第二有机基团是C6H4SO3 -Na+或C6H4CO2 -Na+。
13.权利要求11的改性碳产品,其中所说的第二有机基团在碳上的浓度低于2.4μmol/m2。
14.权利要求1的改性碳产品,其中所说的有机基团的存在量为所用碳的约0.10-约4.0微摩尔/m2,以碳的CTAB或t面积计。
15.权利要求14的改性碳产品,其中所说的存在量为所用碳的约2.0-约3.3微摩尔/m2,以碳的CTAB或t面积计。
16.一种油墨组合物,包括a)权利要求1的改性碳产品和b)非水性或水性载体。
17.一种涂料组合物,包括a)权利要求1的改性碳产品和b)非水性或水性载体。
18.权利要求16的油墨组合物,其中所说的碳为炭黑、石墨、碳纤维、玻璃碳、细分的碳、活性炭或其混合物。
19.权利要求18的油墨组合物,其中所说的碳为炭黑。
20.权利要求17的涂料组合物,其中所说的碳为炭黑、石墨、碳纤维、玻璃碳、细分的碳、活性炭或其混合物。
21.权利要求20的涂料组合物,其中所说的碳为炭黑。
22.一种涂料组合物,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。
23.一种涂料组合物,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。
24.一种涂料组合物,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。
25.一种涂料组合物,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。
26.一种涂料组合物,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。
27.一种涂料组合物,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。
28.一种涂料组合物,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。
29.一种涂料组合物,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。
30.一种涂料组合物,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。
31.一种涂料组合物,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。
32.一种涂料组合物,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。
33.一种油墨组合物,包括a)权利要求11的改性碳产品和b)非水性或水性载体。
34.一种涂料组合物,包括a)权利要求11的改性碳产品和b)非水性或水性载体。
35.一种水性组合物,包括a)权利要求1的改性碳产品和b)缓冲剂、稳定剂或两者。
36.权利要求35的水性组合物,其中所说的缓冲剂为苯甲酸钠或乙酸钠。
37.一种喷墨油墨组合物,包括a)权利要求1的改性碳产品和b)非水性或水性载体。
38.权利要求37的喷墨油墨组合物,其中所说的碳为炭黑、石墨、碳纤维、玻璃碳、细分的碳、活性炭或其混合物。
39.权利要求38的喷墨油墨组合物,其中所说的碳为炭黑。
40.权利要求1的改性碳产品,其中所说的离子或可电离的基团包括环状或杂环基。
42.一种油墨组合物,包括a)权利要求40的改性碳产品和b)非水性或水性载体。
43一种涂料组合物,包括a)权利要求40的改性碳产品和b)非水性或水性载体。
44.一种喷墨油墨组合物,包括a)权利要求40的改性碳产品和b)非水性或水性载体。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/909,944 | 1997-08-12 | ||
US08/909,944 US5895522A (en) | 1997-08-12 | 1997-08-12 | Modified carbon products with leaving groups and inks and coatings containing modified carbon products |
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CN1130430C true CN1130430C (zh) | 2003-12-10 |
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CN98810037A Expired - Fee Related CN1130430C (zh) | 1997-08-12 | 1998-08-07 | 用于油墨和涂料的具有离去基团的改性碳产品和其组合物 |
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US (2) | US5895522A (zh) |
EP (1) | EP1007595B1 (zh) |
JP (2) | JP4633923B2 (zh) |
KR (1) | KR100546523B1 (zh) |
CN (1) | CN1130430C (zh) |
AR (1) | AR016601A1 (zh) |
AU (1) | AU740370B2 (zh) |
BR (1) | BR9815653B1 (zh) |
CA (1) | CA2300981C (zh) |
DE (1) | DE69812970T2 (zh) |
ES (1) | ES2196593T3 (zh) |
HU (1) | HU224219B1 (zh) |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8060834B2 (en) | 2004-05-04 | 2011-11-15 | Fisher-Rosemount Systems, Inc. | Graphics integration into a process configuration and control environment |
Families Citing this family (131)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6852156B2 (en) | 2000-06-05 | 2005-02-08 | E.I. Du Pont De Nemours And Company | Self-dispersing pigment and process of making and use of same |
US6726686B2 (en) * | 1997-11-12 | 2004-04-27 | Sherwood Services Ag | Bipolar electrosurgical instrument for sealing vessels |
DE69901944T3 (de) | 1998-04-03 | 2009-05-14 | Cabot Corp., Boston | Modifizierte pigmente mit verbesserten dispergierenden eigenschaften |
EP1100849B1 (en) * | 1998-07-24 | 2006-09-06 | Cabot Corporation | Methods for preparing silica-coated carbon products |
US6277183B1 (en) | 1998-10-08 | 2001-08-21 | Cabot Corporation | Ink compositions containing metal oxides |
CA2626296C (en) | 1999-01-20 | 2011-12-13 | Cabot Corporation | Polymer foams comprising chemically modified carbonaceous filler |
EP2316874A1 (en) | 1999-01-20 | 2011-05-04 | Cabot Corporation | Aggregates having attached polymer groups and polymer foams |
DE60002564T2 (de) | 1999-03-05 | 2004-04-08 | Cabot Corp., Boston | Verfahren zur herstellung von farbpigmenten |
AU4170600A (en) | 1999-03-12 | 2000-09-28 | Cabot Corporation | Cationic pigments and aqueous compositions containing same |
EP1218457A1 (en) * | 1999-08-09 | 2002-07-03 | Cabot Corporation | Ink compositions having modified pigments with high or low treatment levels |
JP4510256B2 (ja) * | 1999-09-17 | 2010-07-21 | キヤノン株式会社 | インク、インクセット、インクカートリッジ、カラー画像記録装置および画像記録方法 |
ATE239770T1 (de) * | 1999-10-01 | 2003-05-15 | Cabot Corp | Modifizierte pigmente mit sterischen und amphiphilen gruppen |
AU1353501A (en) | 1999-10-28 | 2001-05-08 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
JP4851040B2 (ja) | 1999-10-28 | 2012-01-11 | キャボット コーポレイション | インクジェット用インク、インク、および着色顔料を含有するその他の組成物 |
AU2284701A (en) | 1999-12-20 | 2001-07-03 | Cabot Corporation | Inkjet ink and other ink compositions containing cyclic amides |
EP1244906A1 (en) | 1999-12-30 | 2002-10-02 | Cabot Corporation | Sensors with improved properties |
WO2001051566A1 (en) * | 2000-01-07 | 2001-07-19 | Cabot Corporation | Polymers and other groups attached to pigments and subsequent reactions |
WO2001055245A2 (en) | 2000-01-25 | 2001-08-02 | Cabot Corporation | Polymers containing modified pigments and methods of preparing the same |
US6522522B2 (en) | 2000-02-01 | 2003-02-18 | Cabot Corporation | Capacitors and supercapacitors containing modified carbon products |
US6660075B2 (en) * | 2000-03-16 | 2003-12-09 | Degussa Ag | Carbon black |
US6547381B2 (en) * | 2000-06-23 | 2003-04-15 | Canon Kabushiki Kaisha | Ink, image recording process, ink cartridge, recording unit, ink set, crust-preventing method and image forming apparatus |
US6599356B2 (en) * | 2000-06-28 | 2003-07-29 | Seiko Epson Corporation | Method for manufacturing pigment dispersed liquid, and pigment dispersed liquid, and ink for ink-jet printer recording using said pigment dispersed liquid |
AU2001271652A1 (en) * | 2000-07-06 | 2002-01-21 | Cabot Corporation | Printing plates comprising modified pigment products |
JP5230886B2 (ja) * | 2000-07-06 | 2013-07-10 | キャボット コーポレイション | 修飾顔料生成物、その分散体、およびそれを含有する組成物 |
US6468337B1 (en) | 2000-07-19 | 2002-10-22 | Xerox Corporation | Ink compositions with amine-functionalized pigments |
US6500401B2 (en) | 2000-07-20 | 2002-12-31 | Cabot Corporation | Carbon foams and methods of making the same |
US20020117446A1 (en) * | 2000-09-01 | 2002-08-29 | Agathagelos Kyrlidis | Chromatography and other adsorptions using modified carbon clad metal oxide particles |
US6822781B1 (en) | 2000-10-24 | 2004-11-23 | Cabot Corporation | Gyricon displays containing modified particles |
US7294187B2 (en) * | 2001-01-24 | 2007-11-13 | Ada Foundation | Rapid-hardening calcium phosphate cement compositions |
EP1355998B1 (en) * | 2001-02-02 | 2006-04-05 | Cabot Corporation | Ink compositions comprising salts with polyvalent ions |
US6645287B2 (en) | 2001-04-27 | 2003-11-11 | Cabot Corporation | Coating compositions comprising high t-area carbon products |
US6712894B2 (en) | 2001-05-09 | 2004-03-30 | Cabot Corporation | Method of producing secure images using inks comprising modified pigment particles |
JP4188091B2 (ja) * | 2001-05-15 | 2008-11-26 | イー インク コーポレイション | 電気泳動粒子 |
US20100148385A1 (en) * | 2001-05-15 | 2010-06-17 | E Ink Corporation | Electrophoretic media and processes for the production thereof |
JP4964372B2 (ja) * | 2001-07-17 | 2012-06-27 | 独立行政法人産業技術総合研究所 | 炭素材料の製造方法 |
US6641653B2 (en) | 2001-07-19 | 2003-11-04 | Cabot Corporation | Ink compositions comprising modified colored pigments and methods for preparing the same |
US6641656B2 (en) | 2001-10-17 | 2003-11-04 | Cabot Corporation | Dispersions comprising modified pigments |
JP2006503114A (ja) * | 2002-01-07 | 2006-01-26 | キャボット コーポレイション | 改質ピグメント生成物およびそれを含むブラックマトリクス |
EP1465956A1 (en) * | 2002-01-16 | 2004-10-13 | E.I. Du Pont De Nemours And Company | Smear resistant inkjet inks |
US7001934B2 (en) * | 2002-01-24 | 2006-02-21 | Cabot Coroporation | Inkjet ink systems comprising a gelling agent |
AU2003226020A1 (en) * | 2002-03-27 | 2003-10-13 | Cabot Corporation | Method for attachment of one or more organic groups onto a particle |
US7173078B2 (en) | 2002-04-12 | 2007-02-06 | Cabot Corporation | Process for preparing modified pigments |
US6699319B2 (en) | 2002-05-06 | 2004-03-02 | Cabot Corporation | Process for preparing modified pigments |
US6833026B2 (en) | 2002-05-10 | 2004-12-21 | Cabot Corporation | Modified pigments and process for preparing modified pigments |
US6899754B2 (en) * | 2002-06-06 | 2005-05-31 | E. I. Du Pont De Nemours And Company | Inkjet inks with increased optical density |
JP3771206B2 (ja) * | 2002-09-25 | 2006-04-26 | 松下電器産業株式会社 | 水溶性材料及びパターン形成方法 |
US7045002B2 (en) * | 2002-11-15 | 2006-05-16 | E. I. Du Pont De Nemours And Company | Interactive ink set for inkjet printing |
US20040201658A1 (en) * | 2003-01-16 | 2004-10-14 | Christian Jackson | Inkjet ink set and method of using same |
US7223302B2 (en) * | 2003-01-17 | 2007-05-29 | Cabot Corporation | Methods of preparing aqueous colored pigment dispersions, and inkjet ink compositions |
US6942724B2 (en) * | 2003-04-16 | 2005-09-13 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
US6936097B2 (en) * | 2003-04-16 | 2005-08-30 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
US20050020730A1 (en) | 2003-05-19 | 2005-01-27 | Valentini Jose E. | Inkjet ink |
US20050039631A1 (en) * | 2003-05-23 | 2005-02-24 | Best Kevin J. | Pigmented inkjet ink set |
US20050090599A1 (en) * | 2003-06-06 | 2005-04-28 | Spinelli Harry J. | Aqueous ionically stabilized dispersions |
US20050032930A1 (en) * | 2003-07-02 | 2005-02-10 | Christian Jackson | Inkjet ink |
US7001936B2 (en) * | 2003-07-16 | 2006-02-21 | Lexmark International, Inc. | Pigmented inkjet ink |
DE602004009958T2 (de) * | 2003-09-08 | 2008-08-28 | E.I. Dupont De Nemours And Co., Wilmington | Tintenstrahldrucktinte, tintenkombination und druckverfahren |
US7192472B2 (en) * | 2003-09-18 | 2007-03-20 | E. I. Du Pont De Nemours And Company | Inkjet ink composition |
JP4791369B2 (ja) * | 2003-11-12 | 2011-10-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | インクジェット・インク、インクセットおよび印刷の方法 |
US7018453B2 (en) * | 2003-12-31 | 2006-03-28 | Sun Chemical Corporation | Low VOC web offset heatset inks |
US20050182154A1 (en) * | 2004-01-21 | 2005-08-18 | Berge Charles T. | Inkjet inks containing crosslinked polyurethanes |
US20050256225A1 (en) * | 2004-05-11 | 2005-11-17 | Viola Michael S | Aqueous inkjet ink compositions comprising comb-branched copolymers |
US7351278B2 (en) * | 2004-06-09 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Additive for high optical density inkjet ink |
US7347892B2 (en) * | 2004-08-13 | 2008-03-25 | Xerox Corporation | Phase change inks containing modified pigment particles |
US20060038867A1 (en) * | 2004-08-18 | 2006-02-23 | Valentini Jose E | Inkjet ink with long latency |
CA2583739A1 (en) | 2004-10-15 | 2006-04-27 | Cabot Corporation | High resistivity compositions |
US20060170746A1 (en) * | 2005-01-10 | 2006-08-03 | Christian Jackson | Inkjet ink set |
US7655372B2 (en) | 2005-01-28 | 2010-02-02 | Cabot Corporation | Toners comprising modified pigments and processes for preparing the same |
TW200643114A (en) | 2005-03-24 | 2006-12-16 | Cabot Corp | Fluoroquinolonoquinolones and inkjet ink compositions comprising the same |
JP2009521535A (ja) * | 2005-08-08 | 2009-06-04 | キャボット コーポレイション | ナノチューブを含むポリマー組成物 |
KR101441141B1 (ko) | 2005-10-31 | 2014-09-18 | 캐보트 코포레이션 | 변성 착색제, 및 변성 착색제를 포함하는 잉크젯 잉크조성물 |
JP2007131831A (ja) * | 2005-11-09 | 2007-05-31 | Cheil Industries Inc | ベンゼン化合物で表面処理されたカーボンブラック及びこれを利用したカラーフィルター用ブラックマトリックスに用いるカーボンブラック分散液組成物 |
US7749957B2 (en) | 2006-04-06 | 2010-07-06 | E.I. Du Pont De Nemours And Company | Clay-binding peptides and methods of use |
US8728223B2 (en) | 2006-05-16 | 2014-05-20 | Cabot Corporation | Low viscosity, high particulate loading dispersions |
US8585816B2 (en) * | 2006-05-16 | 2013-11-19 | Cabot Corporation | Low viscosity, high particulate loading dispersions |
KR100725023B1 (ko) * | 2006-10-16 | 2007-06-07 | 제일모직주식회사 | 카도계 수지를 함유한 수지 조성물 및 그에 의한 패턴의 제조방법, 이를 이용한 컬러필터 |
WO2008055245A2 (en) | 2006-10-31 | 2008-05-08 | Sensient Colors Inc. | Inks comprising modified pigments and methods for making and using the same |
CN101646734A (zh) * | 2007-01-24 | 2010-02-10 | 卡伯特公司 | 形成改性颜料的方法 |
US7771523B2 (en) * | 2007-04-20 | 2010-08-10 | E.I. Du Pont De Nemours And Company | Ink jet ink |
US7799121B2 (en) * | 2007-04-20 | 2010-09-21 | E.I. Du Pont De Nemours And Company | Inkjet ink |
US20090020035A1 (en) * | 2007-04-20 | 2009-01-22 | Christian Jackson | Inkjet ink |
EP2201072B1 (en) | 2007-08-23 | 2018-11-14 | Sensient Colors LLC | Self-dispersed pigments and methods for making and using the same |
EP2222801A1 (en) * | 2007-12-18 | 2010-09-01 | E. I. du Pont de Nemours and Company | Aqueous inkjet ink comprising a bleed control agent |
US20090192261A1 (en) * | 2008-01-25 | 2009-07-30 | Waifong Liew Anton | Ink jet inks having improved corrosion resistance |
EP2235121A1 (en) * | 2008-01-25 | 2010-10-06 | E. I. du Pont de Nemours and Company | Ink jet inks having improved corrosion resistance for use in ink jet print heads comprising nickel or nickel alloys |
KR20100116623A (ko) * | 2008-02-19 | 2010-11-01 | 캐보트 코포레이션 | 메조기공성 탄소 블랙 및 그의 제조 방법 |
JP2011521085A (ja) * | 2008-05-22 | 2011-07-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | インクジェットインクと共に用いられる定着インク |
US20100081740A1 (en) * | 2008-09-29 | 2010-04-01 | Christian Jackson | Aqueous inkjet ink comprising self-dispersing pigment |
BRPI1007209A2 (pt) | 2009-01-09 | 2016-07-19 | Cabot Corp | pigmentos modificados contendo composições de tinta para jato de tinta tendo um aumento de condutividade reduzido |
WO2010111343A1 (en) | 2009-03-24 | 2010-09-30 | E. I. Du Pont De Nemours And Company | Pigmented inkjet ink comprising a bleed control agent |
BRPI1014677A2 (pt) | 2009-03-30 | 2016-04-12 | Du Pont | sistemas baseados em peptídeos para distribuição de agentes cosméticos |
US8481678B2 (en) | 2009-03-30 | 2013-07-09 | E I Du Pont De Nemours And Company | Peptide-based tooth whitening reagents |
WO2010118187A2 (en) | 2009-04-07 | 2010-10-14 | Sensient Colors Inc. | Self-dispersing particles and methods for making and using the same |
US8580024B2 (en) | 2009-06-04 | 2013-11-12 | Cabot Corporation | Inkjet ink compositions comprising modified pigments |
EP2484727A4 (en) | 2009-09-30 | 2014-08-20 | Dainippon Printing Co Ltd | Ink Composition |
WO2011150301A1 (en) | 2010-05-27 | 2011-12-01 | E. I. Du Pont De Nemours And Company | Fixer inks for use with ink jet inks |
WO2012016125A2 (en) | 2010-07-30 | 2012-02-02 | Cabot Corporation | Polymeric pigment systems and methods |
TWI465500B (zh) | 2010-09-03 | 2014-12-21 | Cabot Corp | 經修飾充填物及包含其之彈性複合物 |
CN102436142B (zh) | 2010-09-29 | 2013-11-06 | 第一毛织株式会社 | 黑色光敏树脂组合物以及使用其的光阻层 |
KR101367253B1 (ko) | 2010-10-13 | 2014-03-13 | 제일모직 주식회사 | 감광성 수지 조성물 및 이를 이용한 차광층 |
US9238736B2 (en) | 2010-10-15 | 2016-01-19 | Cabot Corporation | Surface modified organic black pigments, surface modified carbon blacks, pigment mixtures using them, and low dielectric black dispersions, coatings, films, black matrices, and devices containing same |
JP2012188644A (ja) * | 2010-11-25 | 2012-10-04 | Dic Corp | インクジェット記録用水性顔料分散液の製造方法 |
KR101486560B1 (ko) | 2010-12-10 | 2015-01-27 | 제일모직 주식회사 | 감광성 수지 조성물 및 이를 이용한 차광층 |
KR101453769B1 (ko) | 2010-12-24 | 2014-10-22 | 제일모직 주식회사 | 감광성 수지 조성물 및 이를 이용한 컬러 필터 |
US8435707B2 (en) | 2011-06-16 | 2013-05-07 | Cabot Corporation | Toner additive comprising carbon-silica dual phase particles |
US9546286B2 (en) | 2011-07-22 | 2017-01-17 | Cabot Corporation | High resistivity coating compositions having unique percolation behavior, and electrostatic image developing systems and components thereof incorporating same |
KR101344786B1 (ko) | 2011-12-02 | 2013-12-26 | 제일모직주식회사 | 컬러필터용 감광성 수지 조성물 및 이를 이용한 컬러필터 |
US9175150B2 (en) | 2012-03-02 | 2015-11-03 | Cabot Corporation | Modified carbon blacks having low PAH amounts and elastomers containing the same |
MX2014010497A (es) | 2012-03-02 | 2014-11-14 | Cabot Corp | Compuestos elastomericos que contienen rellenos modificados y elastomeros funcionalizados. |
NL2011151C2 (en) | 2012-07-13 | 2015-03-24 | Cabot Corp | High structure carbon blacks. |
US20140120339A1 (en) | 2012-10-31 | 2014-05-01 | Cabot Corporation | Porous carbon monoliths templated by pickering emulsions |
KR20140076320A (ko) | 2012-12-12 | 2014-06-20 | 제일모직주식회사 | 감광성 수지 조성물 및 이를 이용한 블랙 스페이서 |
JP2016516105A (ja) | 2013-03-05 | 2016-06-02 | キャボット コーポレイションCabot Corporation | 水性の顔料分散液 |
GB2526023A (en) | 2013-03-12 | 2015-11-11 | Cabot Corp | Aqueous dispersions comprising nanocrystalline cellulose, and compositions for commercial inkjet printing |
JP6173556B2 (ja) | 2013-03-13 | 2017-08-02 | キャボット コーポレイションCabot Corporation | 組み合わされた低誘電率、高抵抗率及び光学濃度特性、ならびに、制御された電気抵抗率を有するフィラー−ポリマー組成物を含むコーティング、それから製造されるデバイス及びその製造方法 |
BR112015022726A2 (pt) | 2013-03-14 | 2017-07-18 | Cabot Corp | materiais poliméricos de núcleo-casca |
WO2015148793A1 (en) | 2014-03-28 | 2015-10-01 | Cabot Corporation | Modified carbon black for oilfield fluids |
WO2016061090A1 (en) | 2014-10-14 | 2016-04-21 | Cabot Corporation | Aqueous inkjet ink compositions |
WO2016187059A1 (en) | 2015-05-15 | 2016-11-24 | Cabot Corporation | Amphoteric polymers and use in inkjet ink compositions |
CN108431142A (zh) | 2015-11-18 | 2018-08-21 | 卡博特公司 | 喷墨油墨组合物 |
JP6860330B2 (ja) * | 2015-12-28 | 2021-04-14 | キヤノン株式会社 | 自己分散顔料の製造方法、インクの製造方法、及びインクジェット記録方法 |
FR3058151B1 (fr) | 2016-10-31 | 2021-04-09 | Cabot Corp | Polymeres pour des encres pour imprimantes a jet d'encre |
WO2019051021A1 (en) | 2017-09-07 | 2019-03-14 | Cabot Corporation | INK COMPOSITIONS FOR INKJET PRINTING |
CN108408717B (zh) * | 2018-03-19 | 2020-01-03 | 中国工程物理研究院激光聚变研究中心 | 一种毫米级多孔二氧化硅/碳杂化球的制备方法 |
CN113165974A (zh) | 2018-10-31 | 2021-07-23 | 卡博特公司 | 包含经化学处理的碳颜料的砌筑组合物 |
CN114174399B (zh) | 2019-06-05 | 2023-11-07 | 超越莲花有限责任公司 | 轮胎胎面 |
EP3960818A1 (en) | 2020-08-24 | 2022-03-02 | Orion Engineered Carbons Ip Gmbh & Co. Kg | Composite carbon black particles |
US20240026094A1 (en) | 2020-12-09 | 2024-01-25 | Beyond Lotus Llc | Methods of preparing a composite comprising never-dried natural rubber and filler |
CN116635454A (zh) | 2020-12-09 | 2023-08-22 | 超越莲花有限责任公司 | 制备具有弹性体和填料的配混物的方法 |
CA3226817A1 (en) | 2021-07-20 | 2023-01-26 | Beyond Lotus Llc | Stored elastomer composites |
WO2023184057A1 (en) | 2022-03-28 | 2023-10-05 | Cabot Corporation | Dispersions of carbon black in alkylene glycol and in situ polymerization of polyester therewith |
Family Cites Families (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US860001A (en) * | 1906-08-02 | 1907-07-16 | Richard D White | Ship's telegraphy. |
US2121535A (en) * | 1934-09-22 | 1938-06-21 | Cabot Godfrey L Inc | Granular product and method of preparing the same |
US2439442A (en) * | 1943-02-06 | 1948-04-13 | Cabot Godfrey L Inc | Process of making hydrophilic carbon black |
US2793100A (en) * | 1952-10-16 | 1957-05-21 | Degussa | Process of modifying carbon black |
US3011902A (en) * | 1954-05-27 | 1961-12-05 | Cabot Corp | Process of manufacturing carbon black pellets for inks |
US2867540A (en) * | 1955-12-30 | 1959-01-06 | Monsanto Chemicals | Modified carbon black product and process |
FR72775E (fr) * | 1958-01-07 | 1960-07-22 | Etude Des Ind Du Petrole Au Po | Noir de carbone soluble dans l'eau et sa préparation |
GB862018A (en) * | 1957-01-16 | 1961-03-01 | Etude Des Ind Du Petrole Au Po | Water-dispersible carbon black and production thereof |
GB910309A (en) * | 1958-07-22 | 1962-11-14 | Dunlop Rubber Co | Rubber compositions |
FR1331889A (fr) * | 1962-08-24 | 1963-07-05 | Bayer Ag | Fabrication de préparations de noir de fumée |
US3317458A (en) * | 1963-10-07 | 1967-05-02 | Degussa | Mixture of carbon black and light filler aqueous suspension added to rubber latex |
DE1231251B (de) * | 1963-11-28 | 1966-12-29 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Diazoverbindungen |
US3335020A (en) * | 1964-03-02 | 1967-08-08 | Huber Corp J M | Modified carbon blacks |
DE1720988B1 (de) * | 1966-08-18 | 1972-05-31 | Japan Gas Chemical Company Inc | Verfahren zur herstellung einer russ-kunstharz-masse |
UST860001I4 (en) * | 1966-12-22 | 1969-03-18 | Defensive publication | |
US3528840A (en) * | 1967-11-15 | 1970-09-15 | Huber Corp J M | Sulfonated carbon black |
US3671476A (en) * | 1969-03-01 | 1972-06-20 | Sumitomo Light Metal Ind | Electrodeposition color coating composition and method for electrodeposition color coating of metal therewith |
DE1948443C3 (de) * | 1969-09-25 | 1981-02-19 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung hochdisperser, homogener aus Siliciumdioxid und RuB bestehender oder diese enthaltender Mischungen |
US3686111A (en) * | 1970-06-22 | 1972-08-22 | Ppg Industries Inc | Non-aqueous polymeric pseudo-dispersion |
US4014844A (en) * | 1970-06-26 | 1977-03-29 | Agence Nationale De Valorisation De La Recherche (Anvar) | Process for grafting polymers on carbon black through free radical mechanism |
DE2355758C2 (de) * | 1973-11-08 | 1983-06-01 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von geschönten Rußen |
GB1506464A (en) * | 1974-05-29 | 1978-04-05 | Degussa | Aqueous carbon black preparation |
DE2825655A1 (de) * | 1978-06-12 | 1979-12-20 | Hoechst Ag | Verfahren zur kontinuierlichen diazotierung von aminen |
DE2908202A1 (de) * | 1979-03-02 | 1980-10-30 | Degussa | Verfahren zur herstellung von wasserhaltigen russpraeparationen |
JPS5626972A (en) * | 1979-08-13 | 1981-03-16 | Mitsubishi Rayon Co Ltd | Oil-containing waste water-treating material comprising modified active carbon |
US4265768A (en) * | 1979-12-26 | 1981-05-05 | Rohm And Haas Company | Ion exchange material prepared from partially pyrolyzed macroporous polymer particles |
DE3115532A1 (de) * | 1980-04-17 | 1982-01-28 | Canon K.K., Tokyo | Tintenstrahl-aufzeichnungsverfahren und aufzeichnungstinte fuer die aufzeichnung auf einem bildempfangsmaterial |
DE3039527C2 (de) * | 1980-10-20 | 1984-02-02 | Chemische Werke Brockhues AG, 6229 Walluf | Färbemittel für zementhaltige Gegenstände |
JPS5938016B2 (ja) * | 1980-11-10 | 1984-09-13 | 呉羽化学工業株式会社 | 塩基性悪臭成分の補集剤及び補集濃縮方法 |
CA1177297A (en) * | 1981-03-30 | 1984-11-06 | Michael G. Blankenship | Polarization retaining single-mode optical fibers and methods of making |
US4452638A (en) * | 1981-05-14 | 1984-06-05 | Union Oil Company Of California | Marker fluid composition for spotting cement in offshore wells |
DE3278360D1 (en) * | 1982-07-09 | 1988-05-26 | Battelle Memorial Institute | Low viscosity stable aqueous dispersion of graft carbon black |
JPS5982467A (ja) * | 1982-10-29 | 1984-05-12 | 三菱レイヨン株式会社 | 炭素繊維の表面処理方法 |
EP0115560A3 (en) * | 1983-02-02 | 1985-09-18 | Won Pyo Hong | Improved portland cement, process for preparing same, and compositions containing same |
JPS62191040A (ja) * | 1986-02-17 | 1987-08-21 | Nippon Denso Co Ltd | 吸着性炭素材およびその製造方法 |
IN168779B (zh) * | 1986-03-24 | 1991-06-01 | Cabot Corp | |
JPS62250073A (ja) * | 1986-04-23 | 1987-10-30 | Asahi Carbon Kk | 表面改質カ−ボンブラツクおよび製造方法 |
JPH068366B2 (ja) * | 1987-04-23 | 1994-02-02 | 株式会社ブリヂストン | タイヤ用ゴム組成物 |
DE3926564A1 (de) * | 1989-08-11 | 1991-02-14 | Hoechst Ag | Neue pigmentzubereitungen auf basis von perylenverbindungen |
EP0429828B1 (en) * | 1989-10-19 | 1994-03-16 | Canon Kabushiki Kaisha | Ink and ink jet recording method, ink cartridge, ink jet device and ink jet recording apparatus using the same |
DE69020540T2 (de) * | 1989-11-21 | 1996-02-22 | Seiko Epson Corp | Tinte zum tintenstrahldruckverfahren. |
US5200164A (en) * | 1990-04-04 | 1993-04-06 | Cabot Corporation | Easily dispersible carbon blacks |
DE4023537A1 (de) * | 1990-07-25 | 1992-01-30 | Degussa | Mit organosiliciumverbindungen chemisch modifizierte russe, verfahren zu deren herstellung und deren verwendung |
US5281261A (en) * | 1990-08-31 | 1994-01-25 | Xerox Corporation | Ink compositions containing modified pigment particles |
US5282887A (en) * | 1990-10-31 | 1994-02-01 | W. C. Richards Company | Conductive coating composition comprising pigment grade carbon |
DE4038000A1 (de) * | 1990-11-29 | 1992-06-04 | Bayer Ag | Kautschukvulkanisate mit verbessertem hysterese-verhalten |
FR2672307B1 (fr) * | 1991-02-01 | 1993-06-04 | Centre Nat Rech Scient | Procede de modification de la surface de materiaux carbones par reduction electrochimique de sels de diazonium, notamment de fibres de carbone pour materiaux composites, materiaux carbones ainsi modifies. |
JPH0667421A (ja) * | 1992-08-19 | 1994-03-11 | Nippon Kayaku Co Ltd | 黒色光重合性組成物及びその黒色硬化膜及びカラーフィルターの製造方法 |
DK0639237T3 (da) * | 1992-11-27 | 1997-12-29 | Basf Ag | Farvestoffer, deres fremstilling og anvendelse til farvning af substrater |
US5401313A (en) * | 1993-02-10 | 1995-03-28 | Harcros Pigments, Inc. | Surface modified particles and method of making the same |
GB9313871D0 (en) * | 1993-07-05 | 1993-08-18 | Secr Defence | Substituted activated carbons |
US5654357A (en) * | 1994-07-12 | 1997-08-05 | Cabot Cororation | Dispersible carbonblack pellets |
IL154538A (en) * | 1994-12-15 | 2009-12-24 | Cabot Corp | The reaction of carbon black with diazonium salts, the resulting carbon black products |
US5554739A (en) * | 1994-12-15 | 1996-09-10 | Cabot Corporation | Process for preparing carbon materials with diazonium salts and resultant carbon products |
US5571311A (en) * | 1994-12-15 | 1996-11-05 | Cabot Corporation | Ink jet ink formulations containing carbon black products |
IL116378A (en) * | 1994-12-15 | 2003-05-29 | Cabot Corp | Non-aqueous coating or ink composition with improved optical properties containing modified carbon product and method of preparation of the composition |
IL116379A (en) * | 1994-12-15 | 2003-12-10 | Cabot Corp | Aqueous inks and coatings containing modified carbon products |
US5559169A (en) * | 1994-12-15 | 1996-09-24 | Cabot Corporation | EPDM, HNBR and Butyl rubber compositions containing carbon black products |
US5575845A (en) * | 1994-12-15 | 1996-11-19 | Cabot Corporation | Carbon black products for coloring mineral binders |
IL116376A (en) * | 1994-12-15 | 2001-03-19 | Cabot Corp | Aqueous ink jet ink compositions containing modified carbon products |
WO1996034916A2 (en) * | 1995-05-01 | 1996-11-07 | Zeneca Limited | Ink composition |
EP0828789B1 (en) * | 1995-05-22 | 2005-09-14 | Cabot Corporation | Elastomeric compounds incorporating silicon-treated carbon blacks |
US5698016A (en) * | 1996-06-14 | 1997-12-16 | Cabot Corporation | Compositions of modified carbon products and amphiphilic ions and methods of using the same |
US5707432A (en) * | 1996-06-14 | 1998-01-13 | Cabot Corporation | Modified carbon products and inks and coatings containing modified carbon products |
-
1997
- 1997-08-12 US US08/909,944 patent/US5895522A/en not_active Expired - Lifetime
-
1998
- 1998-08-06 US US09/129,785 patent/US5968243A/en not_active Expired - Lifetime
- 1998-08-07 IL IL13447298A patent/IL134472A/xx not_active IP Right Cessation
- 1998-08-07 BR BRPI9815653-5A patent/BR9815653B1/pt not_active IP Right Cessation
- 1998-08-07 ID IDW20000321A patent/ID24313A/id unknown
- 1998-08-07 ES ES98938461T patent/ES2196593T3/es not_active Expired - Lifetime
- 1998-08-07 DE DE69812970T patent/DE69812970T2/de not_active Expired - Lifetime
- 1998-08-07 HU HU0003337A patent/HU224219B1/hu not_active IP Right Cessation
- 1998-08-07 WO PCT/US1998/016532 patent/WO1999007794A1/en active IP Right Grant
- 1998-08-07 JP JP2000506285A patent/JP4633923B2/ja not_active Expired - Lifetime
- 1998-08-07 CA CA002300981A patent/CA2300981C/en not_active Expired - Fee Related
- 1998-08-07 AU AU86985/98A patent/AU740370B2/en not_active Ceased
- 1998-08-07 CN CN98810037A patent/CN1130430C/zh not_active Expired - Fee Related
- 1998-08-07 EP EP98938461A patent/EP1007595B1/en not_active Expired - Lifetime
- 1998-08-07 KR KR1020007001446A patent/KR100546523B1/ko not_active IP Right Cessation
- 1998-08-11 MY MYPI98003641A patent/MY117256A/en unknown
- 1998-08-11 AR ARP980103967A patent/AR016601A1/es active IP Right Grant
- 1998-08-11 TW TW87113174A patent/TW574326B/zh not_active IP Right Cessation
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2010
- 2010-08-02 JP JP2010173631A patent/JP5399997B2/ja not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8060834B2 (en) | 2004-05-04 | 2011-11-15 | Fisher-Rosemount Systems, Inc. | Graphics integration into a process configuration and control environment |
US8185219B2 (en) | 2004-05-04 | 2012-05-22 | Fisher-Rosemount Systems, Inc. | Graphic element with multiple visualizations in a process environment |
Also Published As
Publication number | Publication date |
---|---|
JP2001512776A (ja) | 2001-08-28 |
US5895522A (en) | 1999-04-20 |
HUP0003337A2 (en) | 2001-03-28 |
BR9815653B1 (pt) | 2009-01-13 |
MY117256A (en) | 2004-06-30 |
CA2300981A1 (en) | 1999-02-18 |
JP5399997B2 (ja) | 2014-01-29 |
EP1007595B1 (en) | 2003-04-02 |
DE69812970T2 (de) | 2004-01-29 |
DE69812970D1 (de) | 2003-05-08 |
KR20010022844A (ko) | 2001-03-26 |
US5968243A (en) | 1999-10-19 |
WO1999007794A1 (en) | 1999-02-18 |
JP2010265478A (ja) | 2010-11-25 |
CN1275150A (zh) | 2000-11-29 |
CA2300981C (en) | 2008-04-01 |
EP1007595A1 (en) | 2000-06-14 |
AU740370B2 (en) | 2001-11-01 |
IL134472A0 (en) | 2001-04-30 |
TW574326B (en) | 2004-02-01 |
AR016601A1 (es) | 2001-07-25 |
BR9815653A (pt) | 2001-10-30 |
AU8698598A (en) | 1999-03-01 |
ES2196593T3 (es) | 2003-12-16 |
JP4633923B2 (ja) | 2011-02-16 |
ID24313A (id) | 2000-07-13 |
KR100546523B1 (ko) | 2006-01-26 |
IL134472A (en) | 2005-12-18 |
HU224219B1 (hu) | 2005-06-28 |
HUP0003337A3 (en) | 2002-01-28 |
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