CN1246393C - 改进颜料荧光性的方法 - Google Patents
改进颜料荧光性的方法 Download PDFInfo
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- CN1246393C CN1246393C CNB018189997A CN01818999A CN1246393C CN 1246393 C CN1246393 C CN 1246393C CN B018189997 A CNB018189997 A CN B018189997A CN 01818999 A CN01818999 A CN 01818999A CN 1246393 C CN1246393 C CN 1246393C
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- Prior art keywords
- pigment
- dyestuff
- pigment dyestuff
- tensio
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
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- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/005—Special methods of performing the coupling reaction characterised by the coupling medium containing low molecular weight dispersing agents; containing surface active polythylene gylcols
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
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Abstract
本发明涉及一种制备具有增强荧光性的有机颜料的方法,该方法包括用表面活性剂处理所述颜料,和涉及通过所述方法获得的荧光有机颜料。根据本发明的颜料可以用于其中要求耐久性荧光的标识用途。
Description
本发明涉及一种增强有机颜料的荧光强度的方法,通过所述方法获得的有机颜料,以及所述颜料作为着色剂的用途,特别是在标识应用中的用途,例如特殊效果印刷或防伪印刷。
颜料与染料的区别在于它们的物理性能而不是化学组成。与颜料不同,染料在其应用过程中不溶解,且在该过程中失去其晶体或颗粒结构。
通常基于有机染料的荧光着色剂是在彩色印刷油墨、油漆和塑料中常用的一类重要材料,用于赋予所希望的颜色。这些着色剂通常称为工业荧光颜料,通过将荧光染料溶解在合适的介质例如树脂基体中来获得。该树脂基体然后碎裂成特定的尺寸,通常是数十微米,从而可以用作颜料。
一般来说,有机颜料不显示荧光性,或它们的荧光性仅仅是低强度的。现有技术仅仅描述了有限数目的荧光有机颜料,例如荧光颜料黄101,描述在W.Herbst和K.Hunger,Industrial OrganicPigments,第2版,VCH Verlagsgesellschaft,Weinheim,1997,571-572中。
与染料相比,颜料有许多优点,例如它们的良好耐光性或耐候性。
所以,希望赋予有机颜料以荧光性,从而获得能够用于例如特殊效果印刷或防伪印刷用途中的荧光有机颜料,显示与颜料的物理特性固有的有利性能,从而成为上述荧光染料的另一种选择。
美国专利5863459和5904878描述了一种增强黄色和橙色二芳基化物颜料的荧光性的方法,其中先将合成的颜料以干粉形式分离出来,然后将干燥的颜料加入有机溶剂或水中,获得浆料,对该浆料在高压下热处理数小时。与未处理的颜料相比,当用光谱仪检测油墨配料在基材上的荧光时,该现有技术方法获得的光谱响应中最大增加约8%。在有机溶剂例如乙醇中处理颜料浆料,使得荧光强度是通过水处理获得的荧光强度的约两倍。该现有技术的缺点是必须在处理之前分离颜料,且该处理需要有机溶剂以便获得可接受的结果。认为另一缺点是在苛刻条件下处理颜料。
所以,仍然需要这样的荧光有机颜料,它们可以直接获得,且容易进行无现有技术缺点的工艺,且该颜料显示高强度的荧光。
已经发现,当用表面活性剂处理颜料时,有机颜料的荧光强度可以显著提高。
因此,本发明的目的是提供一种制备具有增强荧光性的有机颜料的方法,该方法包括用表面活性剂处理颜料。
作为有机颜料,可以考虑例如偶氮颜料或多环颜料,例如在W.Herbst和K.Hunger,Industrial Organic Pigments,第2版,VCHVerlagsgesellschaft,Weinheim,1997,187页起中描述的那些。
在本发明的优选实施方案中,有机颜料是偶氮颜料,优选黄色或橙色偶氮颜料,和特别是黄色或橙色二偶氮颜料。在这里,优选在W.Herbst和K.Hunger,Industrial Organic Pigments,第2版,VCHVerlagsgesellschaft,Weinheim,1997,237-270页中描述的那些黄色或橙色二偶氮颜料,特别是在该文献中描述的二芳基黄或二芳基橙颜料,例如C.I.颜料黄12,C.I.颜料黄13,C.I.颜料黄14,C.I.颜料黄17,C.I.颜料黄55,C.I.颜料黄63,C.I.颜料黄81,C.I.颜料黄87,C.I.颜料黄90,C.I.颜料黄106,C.I.颜料黄113,C.I.颜料黄114,C.I.颜料黄121,C.I.颜料黄124,C.I.颜料黄126,C.I.颜料黄127,C.I.颜料黄136,C.I.颜料黄152,C.I.颜料黄170,C.I.颜料黄171,C.I.颜料黄172,C.I.颜料黄174,C.I.颜料黄176,C.I.颜料黄188,C.I.颜料橙15,C.I.颜料橙16和C.I.颜料橙44。
特别优选的是这样一种方法,其中有机颜料选自C.I.颜料黄12,C.I.颜料黄13,C.I.颜料黄14,C.I.颜料黄17,C.I.颜料黄63,C.I.颜料黄83和C.I.颜料橙16,特别是C.I.颜料黄12,C.I.颜料黄14,C.I.颜料黄63和C.I.颜料橙16。
另外,特别优选的这样一种方法,其中有机颜料选自C.I.颜料黄127、C.I.颜料黄174、C.I.颜料黄176和C.I.颜料黄188的混合偶合颜料。
在本发明范围内可使用的合适的表面活性剂可以是阴离子、阳离子、非离子、两性或高分子表面活性剂,涵盖所有类型的表面活性化合物,例如乙酸盐、甜菜碱、甘氨酸盐、咪唑啉、丙酸盐、烷基硫酸盐、烷基芳基磺酸盐、烷基芳基醚羧酸盐、烷基芳基醚硫酸盐、烷基醚羧酸盐、烷基醚硫酸盐、磷酸酯、肌氨酸盐、磺基琥珀酸盐、酒石酸盐、酰胺、氨基胺、胺盐、胺、二胺、多胺、咪唑啉、季化物、脂肪醇乙氧基化物、烷基酚乙氧基化物、酰胺乙氧基化物、胺乙氧基化物、酯乙氧基化物、脂肪酸乙氧基化物、甘油酯乙氧基化物、羟烷基酰胺、和氧化胺。这些表面活性剂的细节描述在K.Lindner,Tenside-Textilhilfsmittel-Waschrohstoffe,Bd.1,Wissenschaftliche Verlagsgesellschaft Stuttgart,1964,561-1086,或在Surfactants Europa-a directory of surfactantsavailable in Europe,第3版,G.L.Hollis编辑,The Royal Societyof Chemistry,1995。
可以使用一种表面活性剂或者两种或多种表面活性剂的混合物。
优选阴离子、阳离子或非离子表面活性剂。
1、可以提及阴离子表面活性剂的例子是:
1.1磺基琥珀酸二烷基酯,其中烷基部分是支链的或直链的,例如磺基琥珀酸二丙基酯,磺基琥珀酸二丁基酯,磺基琥珀酸二戊基酯,磺基琥珀酸双(2-乙基己基)酯或磺基琥珀酸二辛基酯。
1.2硫酸化或磺化脂肪酸或脂肪酸的脂肪酸酯,例如硫酸化油酸、反油酸或蓖麻油酸,以及它们的低级烷基酯,例如乙基、丙基或丁基酯。相应的硫酸化油也是十分合适的,例如橄榄油、菜籽油或蓖麻油。
1.3环氧乙烷和/或环氧丙烷与饱和或不饱和脂肪酸、脂肪醇、脂肪胺、脂环族醇或脂族-芳族烃的反应产物,它们被无机含氧酸或多元羧酸酯化封端。这些化合物优选是式R-A-(CH2CH2O)p-Q的化合物,其中R是具有8-22个碳原子的脂族烃基,或具有10-22个碳原子的脂环族或脂族-芳族烃基;A是-O-、-NH-或-CO-O-;Q是无机多元酸的酸基,或多元羧酸的基团,p是1-20的数,优选1-5。基团R-A-例如衍生自高级醇,例如癸醇、月桂醇、十三烷基醇、肉豆蔻醇、鲸醋醇、硬脂醇、油醇、花生醇、氢化松香醇或二十二烷醇;衍生自脂肪胺,例如月桂胺、肉豆蔻胺、硬脂胺、棕榈胺或油胺;衍生自脂肪酸,例如辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸、二十二烷酸、椰油脂肪(C8-C18)酸,癸烯酸、十二碳烯酸、十四碳烯酸、十六碳烯酸、油酸、亚油酸、亚麻酸、二十碳烯酸、二十二碳烯酸或4,7,11-二十二碳三烯-18-炔酸;或衍生自烷基酚,例如丁基酚、己基酚、正辛基酚、正壬基酚、对叔辛基酚、对叔壬基酚、癸基酚、十二烷基酚、十四烷基酚或十六烷基酚。
酸基Q通常衍生自低分子量的二羧酸,例如马来酸、丙二酸、琥珀酸或磺基琥珀酸,并通过酯桥与基团R-A-(CH2CH2O)p-连接。但是,优选Q衍生自无机多元酸,例如正磷酸或硫酸。酸基Q优选是盐的形式,例如是碱金属盐、铵盐或胺盐的形式。这些盐的例子是钠盐、钾盐、铵盐、三甲基胺、乙醇胺、二乙醇胺和三乙醇胺盐。
1.4烷基芳基磺酸,其中烷基部分是支链的或直链的,例如是异丙基、正-或异-丁基、正-或异-戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十二烷基、正十四烷基、正十六烷基或正十八烷基,和其中芳基部分是例如苯基或萘基。合适的烷基芳基磺酸的例子是癸基苯磺酸、十二烷基苯磺酸、十四烷基苯磺酸、十六烷基苯磺酸和十八烷基苯磺酸。
阴离子表面活性剂通常是其碱金属盐(例如钠或钾盐)、其铵盐或其水溶性胺盐的形式。
2.合适的阳离子表面活性剂是例如式R-N(R1R2)xHAc的胺,和鎓盐化合物,例如下式的铵、锍和鏻化合物:
[R-N(R1R2R3)]+×Ac-
[R-S(R1R2R3)]+×Ac-,和
[R-P(R1R2R3)]+×Ac-,
优选胺类,其中R是具有8-22个、优选8-18个碳原子的脂族烃基;R1、R2和R3各自独立地是具有1-4个碳原子的低级脂族烃基,例如甲基或乙基;芳烷基,例如苄基;或芳基,例如苯基;和Ac是阴离子基团,例如硫酸根、氯离子、溴离子或乙酸根。在胺类表面活性剂中,R1和R2可以另外是氢,R1和R2之一可以另外是具有8-22个、优选8-18个碳原子的脂族烃基。
所述阳离子表面活性剂通过常规公知的方法获得,例如从下列物质获得:脂肪酸,例如辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、花生酸、二十二烷酸、椰油脂肪(C8-C18)酸,癸烯酸、十二碳烯酸、十四碳烯酸、十六碳烯酸、油酸、亚油酸、亚麻酸、二十碳烯酸、二十二碳烯酸或4,7,11-二十二碳三烯-18-炔酸;或脂肪醇,例如癸醇、月桂醇、十三烷基醇、肉豆蔻醇、鲸醋醇、硬脂醇、油醇、花生醇、氢化松香醇或二十二烷醇;烷基或芳烷基卤化物,例如甲基溴、乙基溴、甲基氯、苄基溴、苄基氯、正丙基溴、正丁基溴、正戊基溴、正己基溴、正庚基溴、正辛基溴、正壬基溴、正癸基溴、正十二烷基溴、正十四烷基溴、正十六烷基溴或正十八烷基溴。
优选的胺类表面活性剂是N,N-二甲基椰油胺(cocoamine)和N,N-二椰油甲基胺,特别是N,N-二甲基椰油胺。
3.非离子表面活性剂的例子是:
环氧乙烷加成物,选自环氧乙烷与高级脂肪酸、饱和或不饱和脂肪醇、脂肪胺、硫醇、脂肪酸酰胺、脂肪酸羟烷基胺或脂肪胺的加成产物,或与烷基酚或烷基噻吩的加成产物(该加成物优选含有5-100摩尔环氧乙烷/摩尔上述化合物),以及环氧乙烷-环氧丙烷嵌段聚合物和乙二胺-环氧乙烷-环氧丙烷加成物。这些非离子表面活性剂包括:
3.1含有20-100摩尔环氧乙烷/摩尔醇的并具有8-20个碳原子的饱和和/或不饱和脂肪醇的反应产物,优选含有25-80摩尔、优选25摩尔环氧乙烷/摩尔醇的饱和直链C16-C18醇;
3.2含有5-20摩尔环氧乙烷/摩尔酸的并具有8-20个碳原子的饱和和/或不饱和脂肪酸的反应产物;
3.3含有2-25摩尔环氧乙烷/摩尔酚羟基的并具有7-12个碳原子的烷基酚的反应产物,优选含有5-20摩尔环氧乙烷/摩尔酚羟基的单-或二-烷基酚的反应产物,例如含有5摩尔环氧乙烷的壬基酚乙氧基化物;
3.4含有5-20摩尔环氧乙烷/摩尔酰胺的并具有最多20个碳原子的饱和和/或不饱和脂肪酸酰胺的反应产物,优选含有8-15摩尔环氧乙烷/摩尔酰胺的油基酰胺;
3.5含有5-20摩尔环氧乙烷/摩尔胺的并具有8-20个碳原子的饱和和/或不饱和脂肪酸胺的反应产物,优选含有8-15摩尔环氧乙烷/摩尔胺的油基胺;
3.6含有10-80%环氧乙烷且分子量为1000-80000的环氧乙烷-环氧丙烷嵌段聚合物;
3.7环氧乙烷-环氧丙烷与乙二胺的加成物。
根据本发明方法特别优选的表面活性剂是烷基芳基磺酸盐、胺和烷基酚乙氧基化物,特别是十二烷基苯磺酸盐、N,N-二甲基椰油胺、N,N-二椰油甲基胺和壬基酚乙氧基化物。
在本发明方法中,表面活性剂的用量优选是基于颜料量计的0.5-50%重量、更优选1-15%重量和特别是2-10%重量。
在本发明的优选实施方案中,C.I.颜料黄12用N,N-二甲基椰油胺、N,N-二椰油甲基胺、十二烷基苯磺酸或壬基酚乙氧基化物处理。
在本发明的另一优选实施方案中,C.I.颜料黄14用N,N-二甲基椰油胺处理。
在本发明的另一优选实施方案中,C.I.颜料黄63用N,N-二甲基椰油胺处理。
本发明的优选实施方案进一步涉及一种方法,其中C.I.颜料橙16用N,N-二甲基椰油胺处理。
在本发明方法中,优选在分离颜料之前和特别是在制备颜料的过程中用表面活性剂处理颜料。
如果待制备的荧光颜料是偶氮颜料,则优选用表面活性剂进行的处理通过在偶合反应之前将表面活性剂加入反应混合物中来进行,和特别是通过将表面活性剂加入含有偶合组分的溶液或悬浮液中来进行。含有偶合组分的溶液或悬浮液以及表面活性剂然后与按照常规方式预先二偶氮化的胺的溶液或悬浮液反应。偶合的颜料然后通过按照常规方法分离,例如过滤、水洗和干燥。
与未经过表面活性剂处理的相同颜料的荧光强度相比,通过本发明方法获得的颜料的荧光强度得到显著提高。与未处理的颜料相比,在最大强度处的波长通常提高至少10%,优选至少15%和最优选至少20%。
本发明的再一个目的涉及通过上述本发明方法获得的荧光有机颜料,在下文中称为本发明的有机颜料,其中变量具有上述意义和优选含义。
本发明的另一个实施方案涉及一种通过本发明方法获得的有机颜料,其中有机颜料是C.I.颜料黄12,表面活性剂是N,N-二甲基椰油胺、N,N-二椰油甲基胺、十二烷基苯磺酸或壬基酚乙氧基化物。
本发明的另一个实施方案涉及一种通过本发明方法获得的有机颜料,其中有机颜料是C.I.颜料黄14,表面活性剂是N,N-二甲基椰油胺。
本发明的另一个实施方案涉及一种通过本发明方法获得的有机颜料,其中有机颜料是C.I.颜料黄63,表面活性剂是N,N-二甲基椰油胺。
本发明的另一个实施方案涉及一种通过本发明方法获得的有机颜料,其中有机颜料是C.I.颜料橙16,表面活性剂是N,N-二甲基椰油胺。
本发明的有机颜料可以进行后处理以便改进它们的性能,例如它们在油墨、油漆或塑料中的分散性。后处理的方法是颜料生产领域的技术人员公知的。
有用的后处理是使用天然或合成的含酸性基团的树脂使本发明的颜料树脂化。优选可溶于碱性溶液和可以用酸沉积到颜料上的树脂。这些优选的树脂包括例如松香,可以是脂松香、木松香或牛油松香,松香衍生物,例如松香酯、氢化松香、歧化松香、二聚松香或聚合松香,酚树脂和含羧基的马来酸或富马酸树脂。树脂可以作为酸或作为其金属盐或胺盐的形式存在。在后处理中树脂的用量可以在宽范围内变化,可以是基于本发明有机颜料的重量计的1-60%重量,更优选25-55%重量。
本发明的另一目的涉及表面活性剂用于增强有机颜料的荧光性的用途,其中变量具有上述含义和优选含义。
本发明的另一个实施方案涉及本发明的荧光颜料作为着色剂的用途,优选在标识应用中的用途,一般通过公知的方法使用,例如
(a)用于批量着色聚合物,其中聚合物可以是聚氯乙烯、醋酸纤维素、聚碳酸酯、聚酰胺、聚氨酯、聚酰亚胺、聚苯并咪唑、蜜胺树脂、硅氧烷、聚酯、聚醚、聚苯乙烯、聚甲基丙烯酸甲酯、聚乙烯、聚丙烯、聚乙酸乙烯酯、聚丙烯腈、聚丁二烯、聚氯丁二烯或聚异戊二烯,或所述单体的共聚物;
(b)用于制备油漆、油漆体系(特别是汽车漆)、涂料组合物、纸张颜料、印刷颜料、油墨(特别是用于喷墨打印机),和用于绘画和书法目的,以及用于电子照相,例如用于干复印机系统(Xerox方法)和激光打印机;
(c)用于防伪标识目的,例如用于支票、信用卡、现金本、增票、文件、身份证件等,其中要求达到特殊的无错误的颜色印刷;
(d)作为着色剂的添加剂,例如颜料和染料,其中要求达到特殊的颜色色调,特别是明亮色调是优选的;
(e)用于通过荧光标识物品的机械确认,优选用于分类物品的机械确认,例如包括塑料的再利用,各种印刷品或条码是优选的;
(f)用于生产对于多种显示器、标语和标识目的的被动显影元件,例如被动显影元件、标语和交通标志,例如交通灯、安全装置;
(g)在固态下用荧光标识;
(h)用于装饰和艺术目的;
(i)用于改进无机基材例如氧化铝、二氧化硅、二氧化钛、氧化锡、氧化镁(特别是“stone wood”)、硅酸盐、粘土矿物、含钙、含石膏或含水泥的表面,例如涂层或石膏表面;
(j)作为流变改进剂;
(k)在光学光收集系统中,在荧光太阳能收集器(参见Nachr.Chem.Tech.Lab.1980,28,716),在荧光活化显示器(参见Elektronik 1977,26,6),在用于光诱导聚合制备塑料的冷光源中,例如检测材料,例如在制备半导体电路的过程中,用于分析集成半导体元件的微观结构,在光导体中,在摄影过程中,在显示器、照明或影象转化器系统中,其中通过电子、离子或UV辐射来激发,例如在荧光显示器、Braun管或荧光灯中,自身或与其它半导体组合作为含有染料的集成半导体电路的一部分,例如以外延的形式,在化学光致发光系统中,例如在化学光致发光闪光灯,在照射免疫分析或其它光致发光检测过程中,作为信号涂料,优选用于目视加重书写或绘画的笔画或其它图片,用于标出信号和其它用于达到特定目视颜色印象的物品,在染料激光器中,优选作为产生激光束的荧光染料,作为光记录介质和作为Q-开关;
(l)用于转化光的频率,例如用于将短波光转化成长波可见光,或用于将非线性光学中的激光频率扩大到两倍或三倍;
(m)用于示踪剂目的,例如在生物化学、医学、技术和自然科学领域中,其中新的着色剂可以与基材共价连接或通过第二化合价例如氢键或疏水作用(吸收);和
(n)在高灵敏度检测工艺中(参见Z.Analyt.Chem.1985,320,361),特别是作为闪烁器中的荧光着色剂。
本发明颜料的用途列在(a)至(i)中。
以下实施例说明本发明的具体方面,并不在任何方面限制本发明的范围,也不应该理解为如此。在实施例中,所有份数是以重量计,除非另有说明。重量份与体积份之间的关系是千克与升的关系。
实施例1(对比):将4.5份乙酸(100%)和13.3份盐酸(36%)在60份水中的溶液加热到60℃,在快速搅拌的同时将其加入28.7份N-乙酰乙酰苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到750份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到93℃,在该温度下保持30分钟,然后通过添加水冷却到70℃。然后,产物经过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例2:将4.5份乙酸(100%)、13.3份盐酸(36%)和3.5份N,N-二甲基椰油胺在60份水中的溶液加热到60℃,在快速搅拌的同时将其加入28.7份N-乙酰乙酰苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到750份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到93℃,在该温度下保持30分钟,然后通过添加水冷却到70℃。然后,产物经过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例3:将10份乙酸(100%)和4份N,N-二甲基椰油胺在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入28.7份N-乙酰乙酰苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加乙酸(100%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料被加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例4:将4.5份乙酸(100%)、13.3份盐酸(36%)和4份十二烷基苯磺酸在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入28.7份N-乙酰乙酰苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例5:将4.5份乙酸(100%)、13.3份盐酸(36%)和4份含5摩尔环氧乙烷的壬基酚乙氧基化物在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入28.7份N-乙酰乙酰苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例6(对比):将4.5份乙酸(100%)和13.3份盐酸(36%)在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入31.0份N-乙酰乙酰邻联甲苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例7:将4.5份乙酸(100%)、13.3份盐酸(36%)和4份N,N-二甲基椰油胺在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入31.0份N-乙酰乙酰邻联甲苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例8(对比):将4.5份乙酸(100%)和13.3份盐酸(36%)在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入32.3份N-乙酰乙酰邻氯代苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例9:将4.5份乙酸(100%)、13.3份盐酸(36%)和4份N,N-二甲基椰油胺在50份水中的溶液加热到70℃,在快速搅拌的同时将其加入32.3份N-乙酰乙酰邻氯代苯胺在14.5份氢氧化钠(50%)的270份水溶液中的溶液中。所得的浆料通过添加水调节到850份,并通过添加氢氧化钠(15%)调节到pH6.0。然后,该浆料与19.5份3,3’-二氯联苯胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应,同时添加氢氧化钠(15%)以便保持pH4.8。然后,偶合的颜料浆料加热到90℃,在该温度下保持20分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例10(对比):将50份N-乙酰乙酰苯胺和24份氢氧化钠(50%)在300份水中的溶液加入25份甲酸钠在420份水中的溶液中。在快速搅拌的同时,向该溶液中加入20.9份乙酸(100%)。所得的浆料通过添加水和冰在17℃下调节到1500份。然后,该浆料与32.8份邻联茴香胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应。在反应期间加入冰,以防止升温超过20℃。然后,偶合的颜料浆料加热到90℃,在该温度下保持60分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
实施例11:将50份N-乙酰乙酰苯胺和24份氢氧化钠(50%)在300份水中的溶液加入25份甲酸钠在420份水中的溶液中。在快速搅拌的同时,向该溶液中加入6份N,N-二甲基椰油胺在20.9份乙酸(100%)中的溶液。所得的浆料通过添加水和冰在17℃下调节到1500份。然后,该浆料与32.8份邻联茴香胺(它已经按照常规方式经亚硝酸钠和盐酸预先四偶氮化)反应。在反应期间加入冰,以防止升温超过20℃。然后,偶合的颜料浆料加热到90℃,在该温度下保持60分钟,然后通过添加水冷却到70℃。然后,产物经过过滤、水洗以除去可溶性盐,进行干燥,并通过研磨转化成粉末。
由实施例1-11所述的颜料组合物制备油墨,并检测其荧光强度。
油墨如下制备:向聚乙烯容器中加入200克的2.0-2.5毫米玻璃珠、31克的硝基纤维素清漆、51克乙醇和18克颜料。将该混合物在工业分散器上振动45分钟。18克的所得研磨料通过再加入17克硝基纤维素清漆、9克乙醇和2.5克乙酸乙烯酯来过滤(strained)和还原。最终的油墨然后用K-棒涂在非吸收性纸上。
通过计算玻璃侧边的横切面(drawdowns)和使用Perkin-ElmerLS-5B荧光仪检测荧光光谱来检测荧光强度。
下表列出了结果:
表
实施例 | 颜料类型 | 荧光强度 |
1(对比) | C.I.颜料黄12 | 15 |
2 | C.I.颜料黄12 | 28 |
3 | C.I.颜料黄12 | 25 |
4 | C.I.颜料黄12 | 28 |
5 | C.I.颜料黄12 | 18 |
6(对比) | C.I.颜料黄14 | 8 |
7 | C.I.颜料黄14 | 14 |
8(对比) | C.I.颜料黄63 | 20 |
9 | C.I.颜料黄63 | 33 |
10(对比) | C.I.颜料橙16 | 4 |
11 | C.I.颜料橙16 | 11 |
附图
图1显示了根据本发明实施例1(曲线a:无表面活性剂)和实施例2(曲线b:有表面活性剂)获得的C.I.颜料黄12与400-650nm之间的波长关系的光谱响应图。
Claims (12)
1.一种制备具有增强荧光性的有机颜料C.I.颜料黄12的方法,该方法包括在有机颜料的合成过程中用表面活性剂十二烷基苯磺酸盐或壬基酚乙氧基化物处理该有机颜料。
2.一种制备具有增强荧光性的有机颜料C.I.颜料黄14的方法,该方法包括在有机颜料的合成过程中用表面活性剂N,N-二甲基椰油胺处理该有机颜料。
3.一种制备具有增强荧光性的有机颜料C.I.颜料黄63的方法,该方法包括在有机颜料的合成过程中用表面活性剂N,N-二甲基椰油胺处理该有机颜料。
4.一种制备具有增强荧光性的有机颜料C.I.颜料橙16的方法,该方法包括在有机颜料的合成过程中用表面活性剂N,N-二甲基椰油胺处理该有机颜料。
5.根据权利要求1-4任一项的方法,其中表面活性剂的用量是基于有机颜料量计的0.5-50%重量。
6.根据权利要求1的方法获得的有机颜料,其中有机颜料是C.I.颜料黄12,表面活性剂是十二烷基苯磺酸或壬基酚乙氧基化物。
7.根据权利要求2的方法获得的有机颜料,其中有机颜料是C.I.颜料黄14,表面活性剂是N,N-二甲基椰油胺。
8.根据权利要求3的方法获得的有机颜料,其中有机颜料是C.I.颜料黄63,表面活性剂是N,N-二甲基椰油胺。
9.根据权利要求4的方法获得的有机颜料,其中有机颜料是C.I.颜料橙16,表面活性剂是N,N-二甲基椰油胺。
10.一种增强颜料标识组合物的荧光性的方法,该方法包括用选自烷基芳基磺酸盐、式R-N(R1R2)-HAc的胺和烷基酚乙氧基化物的表面活性剂处理二芳基黄或二芳基橙有机颜料,
其中R是具有8-22个碳原子的脂族烃基,R1和R2各自独立地是氢或具有1-4个碳原子的脂族烃基,或R2是具有8-22个碳原子的脂族烃基,及
Ac是硫酸根、氯离子、溴离子或乙酸根。
11.根据权利要求10的方法,其中所述二芳基黄或二芳基橙有机颜料用基于所述颜料量计0.5-50%重量的表面活性剂处理。
12.根据权利要求10的方法,其中所述具有增强荧光性的经表面处理的颜料选自:
经十二烷基苯磺酸盐或壬基酚乙氧基化物处理过的C.I.颜料黄12,
经N,N-二甲基椰油胺处理过的C.I.颜料黄14,
经N,N-二甲基椰油胺处理过的C.I.颜料黄63,和
经N,N-二甲基椰油胺处理过的C.I.颜料橙16。
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JP4573088B2 (ja) * | 2002-05-29 | 2010-11-04 | Dic株式会社 | 有機顔料組成物の製造方法および顔料分散体 |
EP1422281A1 (en) * | 2002-11-19 | 2004-05-26 | Ciba SC Holding AG | Organic electroluminescent element |
AU2004224246B2 (en) * | 2003-03-25 | 2010-10-28 | Fluorotechnics Pty Limited | Method of enhancing fluorescence |
AU2003901361A0 (en) * | 2003-03-25 | 2003-04-10 | Fluorotechnics Pty Limited | Method of enhancing fluorescence |
JP4787510B2 (ja) * | 2005-02-04 | 2011-10-05 | 大日精化工業株式会社 | 蛍光性着色組成物、着色方法および着色物品 |
US7662308B2 (en) * | 2006-08-07 | 2010-02-16 | Ciba Specialty Chemicals Corporation | Polyhedral oligomeric silsesquioxane (POSS) based fluorescent colorants |
US20100019169A1 (en) * | 2007-01-29 | 2010-01-28 | Michigan Molecular Institute | Remote laser interrogation of threat clouds and surfaces |
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JPH06272049A (ja) * | 1993-03-17 | 1994-09-27 | Maruman Golf Corp | カラーニッケル複合めっき被膜の形成法 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105238095A (zh) * | 2015-10-15 | 2016-01-13 | 姜堰区喜鹊湖化工厂 | 一种颜料橙16的制备方法 |
Also Published As
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DE60125403D1 (de) | 2007-02-01 |
AU2002229542A1 (en) | 2002-05-27 |
ATE348863T1 (de) | 2007-01-15 |
KR20030048473A (ko) | 2003-06-19 |
US6923856B2 (en) | 2005-08-02 |
BR0115433A (pt) | 2003-10-07 |
US20040011251A1 (en) | 2004-01-22 |
MXPA03004224A (es) | 2003-09-22 |
JP2004514045A (ja) | 2004-05-13 |
US7160371B2 (en) | 2007-01-09 |
DE60125403T2 (de) | 2007-10-11 |
EP1334156A1 (en) | 2003-08-13 |
WO2002040595A1 (en) | 2002-05-23 |
CN1474860A (zh) | 2004-02-11 |
CA2427904A1 (en) | 2002-05-23 |
EP1334156B1 (en) | 2006-12-20 |
US20050218378A1 (en) | 2005-10-06 |
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