CN114026091A - 有机荧光化合物的新晶型 - Google Patents
有机荧光化合物的新晶型 Download PDFInfo
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- CN114026091A CN114026091A CN202080043837.8A CN202080043837A CN114026091A CN 114026091 A CN114026091 A CN 114026091A CN 202080043837 A CN202080043837 A CN 202080043837A CN 114026091 A CN114026091 A CN 114026091A
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Abstract
本发明涉及下式化合物的新晶型及其制备方法。该化合物可用于油墨、油漆和塑料的组合物中,尤其是用于宽范围的印刷***中,并且特别适用于安全应用。
Description
本发明涉及一种荧光化合物的新晶型及其制备方法。该化合物可用于油墨、油漆和塑料的组合物中,尤其是用于宽范围的印刷***中,并且特别适用于安全应用。
WO2017/121833涉及具有刚性2,2'-联苯氧基桥的苝二酰亚胺,其可用于颜色转换器中以改进LED的发光效率和用于安全印刷的印刷油墨配制剂中。
DE102006020190描述了苝类染料在水中的纳米分散体,其可用作例如瓮染料或媒染料,用作油墨、油漆和塑料的纳米颜料,用于标记和测试应用以及用于药物中的示踪剂应用。
在DE3545004A1的实施例2中,描述了下式化合物的合成:
令人惊讶地发现下式化合物的新晶型:
(1)(化合物(1)的晶型B),比DE3545004A1中描述的化合物(1)的晶型A更热稳定。化合物(1)的该新晶型显示出对化学品和溶剂的高耐性,而不损失它们的其他优点,例如良好的光稳定性和良好的热稳定性。它们可有利地用作安全印刷,尤其是钞票印刷的荧光化合物。
X射线衍射图用Cu-Kα辐射测量。当然,可以理解,d值和散射角(2θ)受由于+/-0.2(散射角)的实验误差引起的波动的影响。
化合物(1)的新晶型比其特征在于X射线衍射图具有对应于9.2、11.1、13.3和14.9的2θ散射角的衍射峰的化合物(1)的晶型(化合物(1)的晶型A)更稳定。
在另一方面中,本发明提供了一种用于安全印刷的印刷油墨配制剂,其包含如上文和下文所定义的化合物(1)的新晶型。
在另一方面中,本发明提供了一种安全文件,其包含基材和如上文和下文所定义的化合物(1)的新晶型。
在另一方面中,本发明提供了一种可通过印刷方法获得的安全文件,其中使用包含如上文和下文所定义的化合物(1)的新晶型的印刷油墨配制剂。
图1显示了DE3545004A1所述的化合物(1)的晶型A的粉末X射线衍射(PXRD)图。
图2描述了本发明化合物(1)的晶型B的PXRD图。
化合物(1)的新晶型的特征在于图2中所示的PXRD图。
通常,化合物(1)具有至少一种下列有利性质:
-高摩尔消光系数,
-高荧光量子产率,
-良好的耐化学品牢度,特别是耐次氯酸盐漂白牢度和耐溶剂(如甲苯、丙酮或二氯甲烷)牢度,
-良好的耐沸水牢度,
-良好的耐光牢度,
-良好的热稳定性,
-与多种配制剂,特别是用于安全印刷的印刷油墨配制剂的高相容性。
化合物(1)的新晶型(化合物(1)的晶型B)比DE3545004A1中所述的化合物(1)的晶型A更热稳定。如本申请实施例1所示,化合物(1)的晶型B是热力学稳定的晶型,因此与化合物(1)的晶型A相比,其特征在于改善的加工稳定性(对于较高温度操作没有问题)、加工性、再现性和储存稳定性。此外,化合物(1)的晶型B具有更高的有序度,因为它每单位晶胞有4个分子,而化合物(1)的晶型A每单位晶胞有6个分子。
本发明的式(1)化合物的新晶型可通过将其特征在于X射线衍射图具有对应于9.2、11.1、13.3和14.9的2θ散射角的衍射峰的式(1)化合物的晶型在升高的温度下加热5分钟至12小时来制备。
如果使用二甲基甲酰胺作为溶剂,则将混合物在100-120℃下回流1-10小时,通过加入乙酸沉淀固体,并通过在冰乙酸中重结晶并用乙酸、乙醇和水洗涤来纯化。参见本申请的实施例1。
化合物(1)的新晶型或根据上文或下文所述的方法获得的化合物(1)的新晶型尤其可用于安全印刷、用于着色涂料、印刷油墨和塑料、用于数据存储、用于光学标签、用于文件中的安全标签和用于品牌保护、用于太阳能集热器、用于光波导、用作农业的波长转换材料或用作生物分子的荧光标记。
化合物(1)的新晶型也可以以混合物的形式使用,所述混合物包含化合物(1)的新晶型和至少一种不同于化合物(1)的新晶型的其他荧光化合物。合适的其他荧光化合物原则上是与化合物(1)的新晶型相容的所有已知类型的荧光化合物。合适的其他荧光化合物例如为香豆素类、类、苯并噁唑类、阴丹士林类、苯并噻唑类、苯并二唑类、联吡啶衍生物、稀土金属配位化合物、无色无机荧光材料以及日光荧光有机材料,例如苝类、呫吨类、吖啶类、马来酰亚胺类、萘二甲酰亚胺类、颜料黄101(=2,2'-二羟基萘醛连氮(Gelb S 0790))、Irgazin GelGF(1,2,3,4-四氯苯并[4,5]咪唑并[2,1-a]异吲哚-11-酮)。
取决于所选的应用,化合物(1)的新晶型通常可以以10ppm至25%,优选100ppm至10%的浓度使用。
本发明还涉及包含荧光化合物(1)的新晶型或根据上文或下文所述的方法获得的化合物(1)的新晶型的塑料材料。优选地,塑料材料包括至少一种热塑性聚合物。优选地,热塑性聚合物选自:
-均聚物和共聚物,其包含至少一种选自C2-C10单烯烃、1,3-丁二烯、2-氯-1,3-丁二烯、乙烯醇及其C2-C10烷基酯、氯乙烯、偏二氯乙烯、丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、C1-C10醇的丙烯酸酯和甲基丙烯酸酯、乙烯基芳族化合物、(甲基)丙烯腈、马来酸酐和烯属不饱和单-和二羧酸的共聚单体,
-乙烯醇缩醛的均聚物和共聚物,
-聚乙烯酯,
-聚氯乙烯,
-聚碳酸酯,
-聚酯,
-聚醚,
-聚醚酮,
-热塑性聚氨酯,
-聚硫醚,
-聚砜,
-聚醚砜,
-纤维素烷基酯,
-聚丙烯,
-聚对苯二甲酸乙二醇酯
及其两种或更多种的混合物。
作为实例,可以提及具有相同或不同醇结构部分的聚丙烯酸酯,所述醇结构部分选自C4-C8醇(特别是丁醇、己醇、辛醇和2-乙基己醇)、聚碳酸酯、聚甲基丙烯酸甲酯(PMMA)、甲基丙烯酸甲酯、丙烯酸丁酯共聚物、丙烯腈-丁二烯-苯乙烯共聚物(ABS)、乙烯-丙烯共聚物、乙烯-丙烯-二烯共聚物(EPDM)、聚苯乙烯(PS)、苯乙烯-丙烯腈共聚物(SAN)、丙烯腈-苯乙烯-丙烯酸酯(ASA)、苯乙烯-丁二烯-甲基丙烯酸甲酯共聚物(SBMMA)、苯乙烯-马来酸酐共聚物、苯乙烯-甲基丙烯酸共聚物(SMA)、聚甲醛(POM)、聚乙烯醇(PVAL)、聚乙酸乙烯酯(PVA)、聚乙烯醇缩丁醛(PVB)、聚己内酯(PCL)、聚羟基丁酸(PHB)、聚羟基戊酸(PHV)、聚乳酸(PLA)、乙基纤维素(EC)、乙酸纤维素(CA)、丙酸纤维素(CP)和乙酸/丁酸纤维素(CAB)。
优选地,塑料材料包括选自如下组的聚合物,特别是由选自如下组的聚合物组成:聚酯、聚碳酸酯(PC)、聚苯乙烯(PS)、聚甲基丙烯酸甲酯(PMMA)、聚氯乙烯、聚酰胺、聚乙烯、聚丙烯、苯乙烯/丙烯腈(SAN)、丙烯腈/丁二烯/苯乙烯(ABS)及其两种或更多种的混合物。特别优选聚碳酸酯、聚酯或聚甲基丙烯酸甲酯。
塑料材料可进一步包含合适的稳定剂以稳定聚合物。该稳定剂是本领域技术人员已知的,包括抗氧化剂、UV吸收剂、光稳定剂、受阻胺光稳定剂、抗臭氧剂等,特别是受阻胺光稳定剂。术语“受阻胺光稳定剂”是指通常由2,2,6,6-四烷基哌啶表示的化合物类别的位阻胺。
在塑料材料包含稳定剂的情况下,基体材料优选包含其量为0.001-10重量%的稳定剂,基于所有塑料材料的总重量。
根据一个优选实施方案,塑料材料由聚合材料组成。
安全印刷是处理诸如货币、护照、防篡改标签、股票、邮票、身份证等物品的印刷的领域。安全印刷的主要目的是防止伪造、篡改或假冒。
在自动钞票处理领域中,荧光起着重要的作用。大多数实际流通的货币不仅带有可见的彩色印刷物,而且带有仅通过UV光照射才能检测到的特定特征。通常,实施这些荧光特征以供自动货币处理设备在银行和售货应用(自动柜员机、自动售货机等)中使用,以便识别确定的货币钞票并验证其真实性,特别是将其与彩色复印机制作的复制品区分开。
所有安全文件都需要具有良好的稳定性和耐久性。在钞票的情况下,这些要求是极端的,因为钞票经受公众最苛刻的使用条件—它们经受折叠、压皱等引起的材料应力,经受磨损,暴露于天气,暴露于体液如汗液,洗涤,干洗,熨烫等—并且在经受这些之后,预期它们像开始时那样易读。此外,尽管遭受上述条件,但重要的是,文件应具有合理的寿命,理想地为数年。在此期间,文件和因此位于其上的油墨(包括不可见的安全标记)应当抗褪色或变色。因此,用于安全印刷工艺的任何油墨在固化时应当是牢固的、耐水的、耐各种化学品的和柔性的。此外,由于某些国家正在抛弃使用纸作为钞票的基材,所采用的印刷油墨配制剂应当可用在塑料和纸上。化合物(1)的新晶型由于其独特的应用性能而特别适用于安全印刷用的印刷油墨配制剂,尤其用于钞票的印刷油墨配制剂。
在安全印刷中,将化合物(1)的新晶型加入印刷油墨配制剂中。合适的印刷油墨是基于颜料或染料的水基、油基或溶剂基印刷油墨,其用于喷墨印刷、柔性版印刷、丝网印刷、凹版印刷、胶版印刷、激光印刷或凸版印刷以及用于电子照相术。用于这些印刷方法的印刷油墨通常包含溶剂、粘合剂以及各种添加剂,例如增塑剂、抗静电剂或蜡。用于胶版印刷和凸版印刷的印刷油墨通常被配制成高粘度的糊状印刷油墨,而用于柔性版印刷和凹版印刷的印刷油墨通常被配制成具有相对低粘度的液体印刷油墨。
在本发明的上下文中,表述“印刷油墨”还涵盖除化合物(1)的新晶型以外还包含着色剂的配制剂。表述“印刷油墨”还涵盖不含着色剂的印刷漆。
本发明的用于安全印刷的印刷油墨配制剂优选包含:
a)如上所定义的化合物(1)的新晶型或根据上文或下文所述的方法获得的化合物(1)的新晶型,
b)聚合性粘合剂,
c)溶剂,
d)任选地,至少一种着色剂,和
e)任选地,至少一种其他添加剂。
印刷油墨的合适组分是常规的,并且是本领域技术人员公知的。该类组分的实例描述于“Printing Ink Manual”,第四版,Leach R.H.等(编辑),Van Nostrand Reinhold,Wokingham(1988)中。印刷油墨及其配制剂的细节也公开在“Printing Ink”,Ullmann'sEncyclopedia of Industrial Chemistry,第六版,1999年电子版中。IR吸收凹版油墨配制剂的配方描述在US20080241492A1中。上述文献的公开内容在此引入作为参考。
本发明的印刷油墨配制剂通常包含0.0001-25重量%,优选0.001-5重量%,特别是0.01-0.1重量%的组分a),基于印刷油墨配制剂的总重量。
化合物(1)的新晶型以溶解形式或固体形式(以细碎分散状态)存在于印刷油墨配制剂中。
本发明的印刷油墨配制剂通常包含5-74重量%,优选10-60重量%,更优选15-40重量%的组分b),基于印刷油墨配制剂的总重量。
用于本发明印刷油墨配制剂的合适聚合物粘合剂b)例如选自天然树脂、酚树脂、酚改性树脂、醇酸树脂、聚苯乙烯均聚物和共聚物、萜烯树脂、有机硅树脂、聚氨酯树脂、脲-甲醛树脂、三聚氰胺树脂、聚酰胺树脂、聚丙烯酸酯、聚甲基丙烯酸酯、氯化橡胶、乙烯基酯树脂、丙烯酸类树脂、环氧树脂、硝化纤维素、烃树脂、乙酸纤维素及其混合物。
本发明的印刷油墨配制剂还可包含通过固化工艺形成聚合物粘合剂的组分。因此,本发明的印刷油墨配制剂也可配制成可能量固化的,例如能够通过UV光或EB(电子束)辐射固化。在该实施方案中,粘合剂包含一种或多种可固化的单体和/或低聚物。相应的配制剂是本领域所已知的,并且可参见标准教科书,例如系列“Chemistry&Technology ofUV&EB Formulation for Coatings,Inks&Paints”,于1997-1998年由John Wiley&Sons与SITA Technology Limited联合以7卷出版。
合适的单体和低聚物(也称为预聚物)包括环氧丙烯酸酯、丙烯酸酯化的油、氨基甲酸酯丙烯酸酯、聚酯丙烯酸酯、有机硅丙烯酸酯、丙烯酸酯化的胺和丙烯酸类饱和树脂。进一步的细节和实例在“Chemistry&Technology of UV&EB Formulation for Coatings,Inks&Paints”,第II卷:Prepolymers&Reactive Diluents,编辑G Webster中给出。
如果使用可固化的聚合物粘合剂,则其可包含反应性稀释剂,即充当溶剂且在固化时引入到聚合物粘合剂内的单体。反应性单体通常选自丙烯酸酯或甲基丙烯酸酯,并且可以是单官能或多官能的。多官能单体的实例包括聚酯丙烯酸酯或甲基丙烯酸酯、多元醇丙烯酸酯或甲基丙烯酸酯,以及聚醚丙烯酸酯或甲基丙烯酸酯。
在印刷油墨配制剂通过UV辐射固化的情况下,通常必须包含至少一种光引发剂以在暴露于UV辐射时引发单体的固化反应。可用的光引发剂的实例可参见标准教科书,例如“Chemistry&Technology of UV&EB Formulation for Coatings,Inks&Paints”,第III卷,“Photoinitiators for Free Radical Cationic and Anionic Polymerisation”,第2版,J.V.Crivello&K.Dietliker,由G.Bradley编辑,于1998年由John Wiley&Sons与SITATechnology Limited联合出版。为了实现有效的固化,还可有利地包含与光引发剂结合的敏化剂。
本发明的印刷油墨配制剂通常包含1-94.9999重量%,优选5-90重量%,特别是10-85重量%的溶剂c),基于印刷油墨配制剂的总重量。
合适的溶剂选自水、有机溶剂及其混合物。就本发明而言,也用作溶剂的反应性单体被认为是上述粘合剂组分b)的一部分。
溶剂的实例包括水;醇,例如乙醇、1-丙醇、2-丙醇、乙二醇、丙二醇、二甘醇和乙氧基丙醇;酯,例如乙酸乙酯、乙酸异丙酯、乙酸正丙酯和乙酸正丁酯;烃,例如甲苯、二甲苯、矿物油和植物油;及其混合物。
本发明的印刷油墨配制剂可包含额外的着色剂d)。优选地,印刷油墨配制剂包含0-25重量%,更优选0.1-20重量%,特别是1-15重量%的着色剂d),基于印刷油墨配制剂的总重量。
合适的着色剂d)选自常规染料,特别是常规颜料。术语“颜料”在本发明的上下文中全面地用于表示所有颜料和填料,实例为彩色颜料、白色颜料和无机填料。这些包括无机白色颜料如二氧化钛,优选金红石形式,硫酸钡,氧化锌,硫化锌,碱式碳酸铅,三氧化锑,锌钡白(硫化锌+硫酸钡),或彩色颜料,实例为铁氧化物,炭黑,石墨,锌黄,锌绿,群青,锰黑,锑黑,锰紫,巴黎蓝或巴黎绿。除无机颜料以外,本发明的印刷油墨配制剂还可包含有机彩色颜料,实例为乌贼染料、藤黄、铁棕、甲苯胺红、对位红、汉撒黄、靛蓝、偶氮染料、蒽醌和靛蓝染料,以及偶氮、二噁嗪、喹吖啶酮、苝、喹酞酮、二酮吡咯并吡咯、酞菁、异吲哚啉、异吲哚啉酮和金属配合物颜料。合适的还有具有空气夹杂物以增加光散射的合成白色颜料,例如分散体。合适的填料例如为铝硅酸盐如长石,硅酸盐如高岭土、滑石、云母、菱镁矿,碱土金属碳酸盐如碳酸钙,例如方解石或白垩形式,碳酸镁,白云石,碱土金属硫酸盐如硫酸钙,二氧化硅等。
本发明的印刷油墨配制剂可包含至少一种添加剂e)。优选地,印刷油墨配制剂包含0-25重量%,更优选0.1-20重量%,特别是1-15重量%的至少一种组分e),基于印刷油墨配制剂的总重量。
合适的添加剂(组分e)选自增塑剂、蜡、催干剂、抗静电剂、螯合剂、抗氧化剂、稳定剂、增粘剂、表面活性剂、流动调节剂、消泡剂、生物杀伤剂、增稠剂等,及其组合。这些添加剂特别用于精细调节印刷油墨的与应用相关的性质,例如粘合性、耐磨性、干燥速率或滑爽性。
特别地,本发明的用于安全印刷的印刷油墨配制剂优选包含:
a)0.0001-25重量%的化合物(1)的新晶型或根据上文或下文所述的方法获得的化合物(1)的新晶型,
b)5-74重量%的至少一种聚合物粘合剂,
c)1-94.9999重量%的至少一种溶剂,
d)0-25重量%的至少一种着色剂,和
e)0-25重量%的至少一种其他添加剂,
其中组分a)至e)的总和为100%。
本发明的印刷油墨配制剂有利地以常规方式制备,例如通过混合各组分。如前所述,化合物(1)的新晶型以(部分)溶解或细碎分散的固体形式存在于印刷油墨配制剂中。在本发明的印刷油墨配制剂中或在单独的油墨配制剂中可以使用额外的着色剂。当在单独的配制剂中使用额外的着色剂时,本发明的印刷油墨配制剂的施加时间通常是不重要的。例如,可首先施加本发明的印刷油墨配制剂,然后用常规印刷油墨套印。然而,该顺序也可以颠倒,或者,作为选择,以与常规印刷油墨的混合物形式施加本发明的印刷油墨配制剂。在每种情况下,印刷物都可用合适的光源读取。
可在本发明的印刷油墨配制剂之前施加底漆。例如,施加底漆以改善对基材的粘合性。还可以施加额外的印刷漆,例如呈覆盖物的形式,以保护印刷的图像。也可以施加额外的印刷漆以用于美学目的,或用于控制与应用相关的性质。例如,可以使用适当配制的额外印刷漆来影响基材表面的粗糙度、电性能或水蒸气冷凝性能。印刷漆通常通过涂漆***在用于印刷本发明印刷油墨配制剂的印刷机上在线施加。
本发明的印刷油墨配制剂也适用于多层材料。多层材料例如由两个或多个塑料箔组成,例如聚烯烃箔、金属箔或金属化的塑料箔,它们例如通过层压或借助合适的层压胶粘剂彼此结合。这些复合材料也可以包括其他功能层,例如气味阻隔层或水蒸气阻隔层。
以下实施例阐述本发明而不限制本发明。
实施例
X射线粉末衍射法:
获得粉末X射线衍射(XRD)图的条件:粉末X射线衍射图通过本领域已知的方法使用具有X’Celerator检测器的PANanalytical X-pert Pro衍射仪,使用CuKα辐射(在45kV和40mA下操作的管)以Bragg-Brentano(反射)几何学获得。数据记录为从3.006至35.006°2θ,步长为0.0167113°2θ,测量时间为每步19.050秒。使用可变的发散和抗散射狭缝来保持5mm的照射样品长度。
对比例1
化合物(1)的晶型A的制备:
该化合物由DE3545004A1已知,其制备描述于DE3545004A1的实施例2中。所得产物(晶体)显示化合物(1)的晶型A的PXRD图。参见图1。
实施例1
将100g对比例1中获得的化合物(1)的固体(化合物(1)的晶型A)悬浮于0.9L二甲基甲酰胺中。将混合物在110℃下搅拌4小时,冷却至室温,加入0.2L乙醇。为了沉淀,加入0.26L 40%乙酸,过滤沉淀物并用40%乙酸洗涤。将所得固体悬浮于0.35L冰乙酸中并在90℃下搅拌4小时,冷却至室温,过滤,在70℃下用40%乙酸、乙醇和水洗涤并干燥,获得75g化合物(1)的新晶型(化合物(1)的晶型B)。
化合物(1)的晶型B的特征在于以下X射线衍射图:
散射角(2θ) | d间距(埃) | 相对强度(%) |
4.9±0.2 | 17.96014 | 28.91 |
8.0±0.2 | 11.03162 | 78.42 |
12.3±0.2 | 7.17132 | 54.71 |
13.1±0.2 | 6.74129 | 26.63 |
14.0±0.2 | 6.32307 | 77.81 |
14.4±0.2 | 6.13231 | 100 |
15.5±0.2 | 5.73131 | 17.26 |
17.1±0.2 | 5.19731 | 20.7 |
19.9±0.2 | 4.45561 | 24.99 |
21.3±0.2 | 4.17184 | 27.55 |
23.7±0.2 | 3.74982 | 15.27 |
参见图2。
应用实施例1—UV油墨
在60mL广口瓶中,在Speedmixer装置中混合0.1g化合物(1)的晶型B、100gPE 46T和3g二苯基(2,4,6-三甲基苯甲酰基)氧化膦(或(2,4,6-三甲基苯甲酰基)苯基次膦酸乙酯)。用12(或24)μm螺旋绕线棒在PET箔上制备刮涂物。在UV带(具有Hg灯(UT 51072-0004)的Technigraf Aktiprint T/e)下,在120W/cm2下固化涂覆的PET箔3次。获得的膜显示出明亮的荧光。
应用实施例2—UV油墨
将0.1g化合物(1)的晶型B溶解在7gDPGDA(二丙二醇二丙烯酸酯)中。将3g184溶解在7gDPGDA中。将两种溶液加入83gUA 9048中,并通过手动或在speedmixer设备中混合。用具有汞灯(UT 51072–0004)的Technigraf Aktiprint T/e在120W/cm2和20m/分钟,或在120W/cm2下2×40m/分钟下固化位于PET膜上的使用24μm螺旋绕线棒获得的刮涂膜。获得的膜显示出明亮的荧光。
应用实施例3—UV油墨
在Speedmixer DAC 400.1FVZ中,将0.125g化合物(1)的晶型B、100gUA 9072、25gDPGDA和6.25g二苯基(2,4,6-三甲基苯甲酰基)氧化膦与5个直径为4mm的玻璃珠在60mL广口瓶中混合2*140分钟。在Luerence4001/50μm上用12μm螺旋绕线棒刮涂,在UV固化(3*120W/cm2)之后显示出强的明亮荧光。
应用实施例4—氯乙烯共聚物油墨
在Scandex中,将0.4g化合物(1)的晶型B的39.6g氯乙烯树脂溶液(VINNOL E 15/48A 10%的乙酸乙酯/甲基乙基酮/甲基异丁基酮=20:30:47溶液)在有50g直径为2mm的玻璃珠的100mL玻璃广口瓶中分散30分钟。用24μm螺旋绕线棒在乙酸酯膜上制备刮涂物。该膜显示出明亮的荧光。
Claims (13)
2.根据权利要求1所述的化合物(1)的晶型,其特征在于其比特征在于X射线衍射图具有对应于9.2、11.1、13.3和14.9的2θ散射角的衍射峰的式(1)化合物的晶型更稳定。
3.一种制备根据权利要求1或2所述的化合物(1)的晶型的方法,其包括在溶剂中在回流下5分钟至12小时加热特征在于X射线衍射图具有对应于9.2、11.1、13.3和14.9的2θ散射角的衍射峰的式(1)化合物的晶型。
4.根据权利要求3所述的方法,其中溶剂为二甲基甲酰胺,并将混合物在100-120℃下加热1-10小时。
5.根据权利要求3或4所述的方法,其中在加热混合物后,通过加入乙酸沉淀固体,并通过在冰乙酸中重结晶纯化。
6.根据权利要求1或2所述的化合物(1)的晶型或根据权利要求3-5中任一项所述的方法获得的化合物(1)的晶型的用途,其用于安全印刷、用于着色涂料、印刷油墨和塑料、用于数据存储、用于光学标签、用于文件中的安全标签和用于品牌保护、用于太阳能集热器、用于光波导、用作农业的波长转换材料或用作生物分子的荧光标记。
7.一种包含至少一个荧光膜层的制品,所述膜层包含聚合物基体、根据权利要求1或2所述的化合物(1)的晶型或根据权利要求3-5中任一项所述的方法获得的化合物(1)的晶型。
8.用于安全印刷的印刷油墨配制剂,其包含:
a)如权利要求1或2所定义的化合物(1)的晶型或根据权利要求3-5中任一项所述的方法获得的化合物(1)的晶型,
b)聚合物粘合剂,
c)溶剂,
d)任选地,至少一种着色剂,和
e)任选地,至少一种其他添加剂。
9.根据权利要求8所述的印刷油墨配制剂,其包含:
a)0.0001-25重量%的化合物(1)的晶型或根据权利要求3-5中任一项所述的方法获得的化合物(1)的晶型,
b)5-74重量%的至少一种聚合物粘合剂,
c)1-94.9999重量%的至少一种溶剂,
d)0-25重量%的至少一种着色剂,和
e)0-25重量%的至少一种其他添加剂,
其中组分a)至e)的总和为100%。
10.安全文件,其包含基材和如权利要求1或2所定义的化合物(1)的晶型或根据权利要求3-5中任一项所述的方法获得的化合物(1)的晶型。
11.可通过印刷方法获得的安全文件,其中使用如权利要求8或9所定义的印刷油墨配制剂。
12.根据权利要求10或11所述的安全文件,其选自钞票、护照、支票、凭证、ID卡或交易卡、邮票和税收标签。
13.一种检测如权利要求10-12中任一项所定义的安全文件的真实性的方法,包括以下步骤:
a)在电磁波谱的UV/VIS范围内测量安全文件的吸收、反射或透射光谱;和
b)将在a)下测量的光谱和/或由其导出的信息与真实安全元件的相应光谱和/或信息进行比较。
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PCT/EP2020/072726 WO2021037575A1 (en) | 2019-08-23 | 2020-08-13 | New crystal form of an organic fluorescent compound |
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EP (1) | EP4017922A1 (zh) |
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DE3545004A1 (de) | 1985-12-19 | 1987-06-25 | Basf Ag | Fluoreszierende aroxysubstituierte perylen-3,4,9,10-tetracarbonsaeurediimide und ihre verwendung zur flaechenmaessigen konzentriertung von licht |
ES2321008T5 (es) | 2005-11-25 | 2012-06-01 | Sicpa Holding Sa | Tinta para huecograbado que absorbe en el infrarrojo |
DE102006020190A1 (de) | 2006-05-02 | 2007-11-08 | Langhals, Heinz, Prof. Dr. | Perylenfarbstoffe als fluoreszierende Nanopartikel in wässriger Phase |
KR20180101493A (ko) | 2016-01-14 | 2018-09-12 | 바스프 에스이 | 강성 2,2'-비페녹시 가교를 갖는 페릴렌 비스이미드 |
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