CN100564059C - 成像组合物、图像记录介质、制备成像材料的方法 - Google Patents
成像组合物、图像记录介质、制备成像材料的方法 Download PDFInfo
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- CN100564059C CN100564059C CNB2004800319219A CN200480031921A CN100564059C CN 100564059 C CN100564059 C CN 100564059C CN B2004800319219 A CNB2004800319219 A CN B2004800319219A CN 200480031921 A CN200480031921 A CN 200480031921A CN 100564059 C CN100564059 C CN 100564059C
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Abstract
一种涂层,其包括均匀分布和溶解在基质和涂层的隐色染料相中的触角。触角易于吸收能量,其可以以特定的图案施加到成像材料。此吸收的能量加热混合物,使得隐色染料和活化剂混合并且反应,引起隐色染料改变颜色,因而产生标记。一种制备成像材料的方法,该方法包括提供具有活化剂和触角的粉末,溶解活化剂/触角粉末以形成活化剂/基质预聚物溶液,提供隐色染料合金,和将隐色染料合金分散到活化剂/基质预聚物溶液中以形成辐射可固化的膏剂。一种图像记录介质,包括具有触角和活化剂的基质,以及作为独立相分散在该基质中的合金。合金包括触角、隐色染料和促进剂。
Description
技术领域
本发明涉及成像组合物及其制备和应用。
背景技术
当用能量如光或热刺激时产生变色的材料可在成像中具有潜在的应用。例如,这种材料可存在于热敏打印纸和瞬时成像胶片中。通常,已知的材料和组合物可需要多层和/或多相膜结构以及其它加工以产生图像(例如瞬时成像胶片如Polaroid)。在传真介质和热敏头介质的情况中,需要大于1J/cm2的高能量输入以实现优良的图像。在多层/多相介质中的组合物可需要控制成色化学品的扩散和其它加工,并且其存在于游离相和层中。大多数热敏和传真纸涂层由通过制备两个以上组分的精细分散体所制备的涂层组成。当施加能量时,这些组分混合并反应,产生着色材料。为了完成必要的混合,粒子需要跨越三个或更多个相或者层接触以及并入新相。因为这些多相和多层,所以需要高能量来进行这个过程。例如,可能需要具有能量密度为3J/cm2的较大功率的二氧化碳激光器以远大于100微秒的曝光时间来产生标记。在有些情况下,这种高能应用可能损害成像基底。在许多情况中,可能希望使用较小强度、较小功率和/或较短的能量施加而更有效地制造可见标记。
或者,可以使用标记组合物,其用于由激光束辐射在模制品表面上形成清晰标记。涂层成色化学品典型地包括隐色染料和酚类显影剂(活化剂)(两者都具有低溶解度),所述酚类显影剂作为游离相分散在可辐射固化的聚合物基质或溶剂/水性涂层中。该涂层还包括一种触角(antenna),其是一种化学物质,具有与成像激光波长对应的高消光系数吸收谱带。然而,触角仅存在于分离相中的一个中,其不会产生对激光辐射的极高效吸收。因而,标记该涂层所需的能量密度是较高的(>0.5J/cm2,并且通常约3J/cm2)。使用这种能量密度可能导致涂层下的涂层和/或基底被烧蚀或损害。使用这种需要高能量密度的可成像涂层可进一步地使得使用这种涂层来标记温度或能量敏感的数据载体(可记录的CD、DVD等)复杂化。鉴于以上所述,需要快速标记涂层和成色材料,其是由低能辐射引发和可寻址的。
发明内容
本发明涉及一种成像化合物:具有触角和活化剂的基质;和作为独立相分散在所述基质中的合金,所述合金具有触角并且进一步具有均匀分布在合金中的隐色染料和促进剂。
本发明的另一个方面包括制备成像材料的方法。该方法包括提供具有活化剂和触角的粉末,溶解该活化剂/触角粉末以形成活化剂/基质预聚物溶液,提供隐色染料合金,和将隐色染料合金分散到该活化剂/基质预聚物溶液中以形成可辐射固化的膏剂。
本发明的另一个方面包括一种图像记录介质,其包括基底,在基底上的基质,该基质具有触角和活化剂,和作为独立相分散在该基质中的合金,该合金具有触角并且进一步具有均匀分布在合金中的隐色染料和促进剂。
附图说明
尽管本说明书最后部分的权利要求详细地指出且清楚地要求了本发明的保护范围,但是当结合附图阅读以下的发明描述将会更容易地弄清本发明,在附图中:
图1显示了根据本发明的实施方案制备成像材料的方法;和
图2显示根据本发明的实施方案的成像介质。
具体实施方式
本发明包括涂层,当用任何合适的能量源如IR辐射、UV辐射或可见光进行标记时,其产生明晰的标记和极好的图像质量。用于当能量刺激时产生变色的材料可包括成色剂如隐色染料和分散在被施加于基底的基质(如辐射固化的丙烯酸酯低聚物和单体)中的活化剂。在特定的实施方案中,在环境条件下隐色染料或活化剂可基本上不溶于基质。在涂层中还存在高效的辐射能吸收体,其具有吸收能量并且将其提供给反应物的功能。于是可以施加能量,其导致活化剂、成色剂或其两者被加热和混合,使得隐色染料被激活和产生标记。
如这里所用,术语“隐色染料”是指一种成色物质,其在未激活的状态是无色或是第一颜色,随后在活化状态,其显现颜色或者从第一颜色变为第二颜色。如这里所用,术语“活化剂”是一种物质,其与隐色染料反应并引起隐色染料改变其化学结构和改变或获得颜色。仅举例来说,活化剂可为能够实现这种改变的酚类或其它给质子物质。术语“触角”是指任何吸收辐射的化合物。触角容易地吸收期望的标记辐射的特定波长。
本发明涂层的特定实施方案包括可辐射固化的聚合物基质,如基于UV可固化的预聚物的基质。触角均匀分布在或溶于基质中。如这里所用,术语触角包括有效吸收来自成像激光的辐射的任何化合物。在一个特定的实施方案中,触角是红外(IR)染料。触角的实例包括但不局限于IR780(Aldrich 42,531-1)、IR783(Aldrich 54,329-2)、Syntec9/1、Syntec9/3或金属络合物(如二硫戊环金属络合物和靛苯胺金属络合物)。也溶于基质中的是酸性(给质子)活化剂(例如显影剂)。涂层还包括合金(非晶、共晶或多晶),所述合金包括隐色染料、促进剂(优选低熔融温度芳族化合物)和触角。用于本发明特定实施方案中的隐色染料是荧烷基化合物。促进剂的存在助于降低高熔融温度荧烷染料的熔融温度,并因此当加热时提供改进的反应性。使用促进剂还便于触角在隐色染料合金中的均匀溶解。该涂层包括两个分离相。第一相包括可辐射固化的聚合物基质,其具有溶于聚合物基质中的酸性活化剂。第二相包括隐色染料的低熔融温度共晶,其在基质中是不可溶的或其具有较低溶解度(如溶解度小于5%,或者最优选小于2%),但作为精细分散体均匀分布在基质中。
本发明的另一个实施方案包括制备可辐射固化的可成像涂层的方法。该方法包括制备活化剂/触角合金。加热活化剂直到熔化,并且触角溶于该熔体中。任选,触角可以被预溶于较小量的低熔融温度有机溶剂(熔融助剂)中,随后加入活化剂并且使其熔化。将热熔体冷却至环境温度并且研磨至较小粒度(典型地低于约20-约50微米)。在一个特定的实施方案中,活化剂包括具有酚基的酸性(给质子)化合物。用于本发明的合适的活化剂包括任何酸性化合物如双酚A、对羟基苯甲酸苄酯、TG-SA(酚,4,4′-磺酰基双[2-(2-丙烯基)]和多酚。用于本发明的合适活化剂应该与触角有优良的溶解性。
任选地,熔融助剂可被加到涂层中以降低涂层中结晶有机物的熔融温度至约50℃-约120℃。用于本发明的合适熔融助剂包括任何对活化剂和触角均为良好溶剂的化合物。熔融助剂的实例包括但不局限于乙二醇的间甲苯基醚、草酸二苄酯和对苯二甲酸二苄酯。
然后通过将研磨的活化剂/触角合金溶解在UV可固化基质的预聚物溶液中制备活化剂/基质预聚物溶液。在该预聚物溶液中活化剂/触角合金的含量可为约2wt%-约90wt%(基于该预聚物溶液的总重量),理想地为约3wt%-约60wt%,最理想地为5-45wt%。研磨的活化剂/触角合金应该溶于预聚物相中使得组分均匀且均相地分配在液相中。制备活化剂/触角合金提供了触角在液体预聚物中改进的溶解性。这是特别有用的,因为许多常规的IR染料在高粘度的预聚物中具有低溶解度。将触角溶解在活化剂熔体中以及随后将该熔体溶解于预聚物中使得触角能够均匀/均相地分布在基质中,并改进了触角对成像激光辐射的敏感性。
通过将触角溶解在促进剂熔体中而制备隐色染料合金(共晶)。然后将隐色染料溶解在促进剂熔体中,导致隐色染料/促进剂/触角合金的形成,其被冷却并研磨成细粉,优选粒度不大于约20微米,更优选小于10微米。用于本发明的一个特定实施方案中的隐色染料是荧烷型的。适用于本发明的可接受的荧烷隐色染料的实例包括具有下式结构的物质:
其中R可以是烷基或芳基或H原子。
用于本发明的促进剂包括结晶有机固体,其熔融温度为约50℃-约150℃,优选熔融温度为约70℃-约120℃。合适的促进剂包括芳族烃(或其衍生物),其为用于本发明的制剂和方法中的隐色染料和触角提供良好的溶剂特征。除溶解隐色染料和触角之外,促进剂也可助于降低隐色染料的熔融温度和使隐色染料合金在非晶状态中稳定(或减慢隐色染料合金再结晶为各组分)。用于本发明的合适促进剂包括但不局限于间三联苯、对苄基联苯、β-萘酚苄醚、1,2-双(3,4-二甲基苯基)乙烷。
通过将敏化隐色染料合金的粉末分散在活化剂/触角合金的可辐射固化的预聚物(漆)溶液中制备UV可固化的膏剂。可辐射固化的预聚合物作为活化剂/触角合金的溶剂并且作为隐色染料合金的分散介质。在活化剂/漆溶液中溶解性差的隐色染料合金主要作为游离相存在于混合物中。例如,合适的可辐射固化的预聚物(漆)可包括具有光致包装(photo package)的UV可固化的基质如丙烯酸酯衍生物、低聚物和单体。光致包装可包括吸收光的物质,其引发漆如二苯甲酮衍生物的固化反应。自由基聚合单体和预聚物的光引发剂的其他实例包括但不局限于噻吨酮衍生物、蒽醌衍生物、苯乙酮和苯偶姻醚。在本发明特定的实施方案中,可期望选择以不引起变色的辐射形式固化的基质。基于阳离子聚合树脂的基质可能需要基于芳族重氮盐、芳族卤鎓盐、芳族锍盐和金属茂化合物的光引发剂。合适的漆或基质也可包括Nor-Cote CDG000(UV可固化的丙烯酸酯单体和低聚物的混合物),其包含光引发剂(羟基酮)和有机溶剂丙烯酸酯(例如甲基丙烯酸甲酯、甲基丙烯酸己酯、丙烯酸β-苯氧基乙酯和丙烯酸六亚甲基酯)。漆或基质的其他适合的组分可包括但不局限于丙烯酸酯化的聚酯低聚物,如CN293和CN294以及CN-292(低粘度聚酯丙烯酸酯低聚物)、SR-351(三羟甲基丙烷三丙烯酸酯)、SR-395(丙烯酸异癸酯)和SR-256(丙烯酸2(2-乙氧基乙氧基)乙酯)(所用这些都获自Sartomer公司)。
热变色的UV可固化的膏剂被印于基底上,随后进行辐射暴光以固化该涂层。应该选择合适的用于可辐射固化漆的光致包装使得光致包装的活化波长不显著地受存在于涂层中的其他物质的阻碍。通过具有按触角吸收所调谐发射波长的激光可使该固化涂层成像。因此,该涂层有效地吸收激光能量(即能量密度水平低至0.1-0.5J/cm2)。
现参考图2中所举例说明的实施方案,显示了成像介质100、能量110、基底120、成像组合物130和悬浮粒子140。成像介质100可包括基底120。基底120可为任何在其上希望制造标记的基底,如仅举例来说,纸(例如标签、票券、收据或文具)、架空幻灯片或介质如CD-R/RW/ROM或DVD-R/RW/ROM的标记表面。
成像组合物130可包括基质、活化剂和辐射吸收化合物如触角。活化剂和触角可溶于基质中。所形成的促进剂/隐色染料/触角(图1的90)合金可基本上不溶于基质中并且可悬浮或分散在基质中作为均匀分布的粒子140。成像组合物130(包括活化剂和触角)可通过任何可接受的方法如仅仅举例来说轧辊、喷涂或丝网印刷而施加于基底。
能量110可指向成像介质100以形成标记或图像。能量形态可变化,取决于可利用的设备、环境条件和期望的结果。可使用的能量的例子包括IR辐射、UV辐射、X-射线或可见光。触角可吸收能量并且加热成像组合物130。加热可使悬浮粒子140达到一定温度,该温度足以引起最初存在于粒子中的成色物质(例如隐色染料)相互扩散(例如粒子140和基质的玻璃态转化温度(Tg)或熔融温度(Tm))。然后,活化剂和染料可反应以形成颜色或对于隐色染料已着色的情况而言改变其颜色。
实施例1和2举例说明本发明的示范性实施方案。应该理解可以进行一些本发明范围内的变型。例如,适用于本发明的触角60可为有效吸收被施加于成像介质以形成标记类型能量的任何材料。仅仅举例来说,以下化合物IR780(Aldrich 42,531-1)(1)、IR783(Aldrich54,329-2)(2)、Syntec9/1(3)、Syntec9/3(4)或金属络合物(如二硫戊环金属络合物(5)和靛苯胺金属络合物(6))可为合适的触角:
其中M1是过渡金属,R1、R2、R3和R4是有或者没有卤素取代基的烷基或芳基,并且A1、A2、A3和A4可以是S、NH或Se;
其中M2是Ni或Cu且R5和R6是有或没有卤素取代基的芳基或烷基。
合适的触角的另外实例包括醌、酞菁、萘酞菁、金属络合物、偶氮、克酮酸鎓(croconium)、方形酸鎓(squarilium)染料和六官能聚酯低聚物。触角的其他实例可见于“Infrared Absorbing Dyes”,Matsuoka,Masaru编,Plenum Press(1990)(ISBN 0-306-43478-4和“Near-infrared Dyes for High Technology Applications”,Daehne,S.;Resch-Genger,U.;Wolfbeis,O.,编,Kluwer Academic Publishers(ISBN 0-7923-5101-0),两者引入本文作为参考。
活化剂(例如双酚-A)和隐色染料90(例如BK-400)可协力发挥作用以产生标记。活化剂和隐色染料可为任何两种物质,当一起反应时其产生变色。当反应时,活化剂可在隐色染料中引发变色(即使隐色染料显影)。在环境温度在基质中隐色染料可具有低溶解度,但当基质被加热到隐色染料合金和基质的熔融温度以上时,溶解度可显著地增加。因此,当加热时,隐色染料可溶解在基质中。因为存在着溶解在基质中的活化剂,隐色染料和活化剂在同相(基质)中终结,因此彼此反应并且产生颜色。成像后快速冷却来稳定溶解在基质中的着色的隐色染料/活化剂复合物。相反在环境条件下,所形成的隐色染料/促进剂/触角合金可基本上不可溶于漆。“基本上不可溶”是指在环境条件下隐色染料在漆中的溶解度是如此低,以至于没有或者极少出现由于染料和活化剂的反应的变色。因此,在如上所述的实施方案中,在环境条件下,活化剂溶解在漆中而隐色染料/促进剂/触角合金作为基质中的固体保持悬浮或分散状态。活化剂可无限制地包括质子供体和酚类化合物如双酚-A和双酚-S。隐色染料可包括荧烷隐色染料。
适用于本发明的隐色染料包括但不局限于荧烷、苯并呋喃酮、氨基-三芳基甲烷、氨基呫吨、氨基噻吨、氨基-9,10-二氢-吖啶、氨基吩噁嗪、氨基吩噻嗪、氨基二羟基-吩嗪、氨基二苯甲烷、氨基氢化肉桂酸(氰基乙烷、隐色甲川)和相应的酯、2(对羟苯基)-4,5-二苯基咪唑、茚满酮、隐色吲达胺、hydrozine、隐色靛类染料、氨基-2,3-二氢蒽醌、四卤-p,p′-二苯酚、2(对羟苯基)-4,5-二苯基咪唑、苯乙基苯胺和其混合物。在本发明的一个方面,隐色染料可是荧烷、苯并呋喃酮、氨基三芳基甲烷或其混合物。合适的荧烷基隐色染料的一些非限制性实例包括3-二乙基氨基-6-甲基-7-苯胺基荧烷、3-(N-乙基-对甲苯氨基)-6-甲基-7-苯胺基荧烷、3-(N-乙基-N-异戊基氨基)-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-甲基-7-(o,p-二甲基苯胺基)荧烷、3-吡咯烷基-6-甲基-7-苯胺基荧烷、3-哌啶基6-甲基-7-苯胺基荧烷、3-(N-环己基-N-甲基氨基)-6-甲基-7-苯胺基荧烷、3-二乙基氨基-7-(间三氟甲基苯胺基)荧烷、3-二丁基氨基-6-甲基-7-苯胺基荧烷、3-二乙基氨基-6-氯-7-苯胺基荧烷、3-二丁基氨基-7-(邻氯苯胺基)荧烷、3-二乙基氨基-7-(邻氯苯胺基)荧烷、3-二正戊基氨基-6-甲基-7-苯胺基荧烷、3-二正丁基氨基-6-甲基-7-苯胺基荧烷、3-(正乙基-正异戊基氨基)-6-甲基-7-苯胺基荧烷、3-吡咯烷基-6-甲基-7-苯胺基荧烷、1(3H)-异苯并呋喃酮,4,5,6,7-四氯-3,3-双[2-[4-(二甲基氨基)苯基]-2-(4-甲氧基苯基)乙烯基]和其混合物。氨基三芳基甲烷隐色染料也可用于本发明,如三(N,N-二甲基氨基苯基)甲烷(LCV);次-三(N,N-二甲基氨基苯基)甲烷(D-LCV);三(N,N-二乙基氨基苯基)甲烷(LECV);次-三(4-二乙基氨基苯基)甲烷(D-LECV);三(N,N-二正丙基氨基苯基)甲烷(LPCV);三(N,N-二正丁基氨基苯基)甲烷(LBCV);双(4-二乙基氨基苯基)-(4-二乙基氨基-2-甲基-苯基)甲烷(LV-1);双(4-二乙基氨基-2-甲基苯基)-(4-二乙基氨基-苯基)甲烷(LV-2);三(4-二乙基氨基-2-甲基苯基)甲烷(LV-3);次-双(4-二乙基氨基苯基)-(4-二乙基氨基-2-甲基苯基)甲烷(D-LV-1);次-双(4-二乙基氨基-2-甲基苯基)(4-二乙基氨基苯基)甲烷(D-LV-2);双(4-二乙基氨基-2-甲基苯基)(3,4-二甲氧基苯基)甲烷(LB-8);具有键合到氨基部分的不同的烷基取代基的氨基三芳基甲烷隐色染料,其中每个烷基独立地选自C1-C4烷基;和具有任何前述结构的氨基三芳基甲烷隐色染料,其进一步地在芳环上被一种或多种烷基取代,其中所述烷基独立地选自C1-C3烷基。其他隐色染料也可以用于本发明并且为本领域技术人员所知。一些这些类型的隐色染料的更详细讨论可见于美国专利3658543和6251571,其全部引入本文作为参考。用于本发明的其他适合的隐色染料的实例可见于Chemistry and Applications of Leuco Dyes,Muthyala,Ramaiha,编;Plenum Press,NewYork,London;ISBN:0-306-45459-9,其全部内容引入本文作为参考。
当加热引起氧化、质子化、开环等时,在未受抑制的金属络合物活化剂和/或未受保护的辅助活化剂的存在下,以上列举的隐色染料可形成具有各种光学特性的染料。尽管许多组合物适用于本发明,但成色组合物可包含至少约3wt%的隐色染料,更具体地说,可以浓度为约4wt%-约20wt%存在。很清楚这些范围仅仅是示例性的,取决于期望的图像特征及其他考虑因素,可使用其它的重量范围。
可接受的荧烷隐色染料的实例包括如式(7)所示的结构:
其中R可为烷基或芳基或H原子。
漆30可为任何合适的用于溶解和/或分散活化剂、触角和成色剂的基质。仅仅举例来说,可接受的漆可包括具有光致包装的UV可固化的基质如丙烯酸酯衍生物、低聚物和单体。光致包装可包括吸收光的物质,其引发漆如二苯甲酮衍生物的固化反应。自由基聚合单体和预聚物的光引发剂的其他实例包括但不局限于噻吨酮衍生物、蒽醌衍生物、苯乙酮和苯偶姻醚类。可期望选择通过以引起变色的辐射类型之外的辐射形式固化的基质。基于阳离子聚合树脂的基质可需要基于芳族重氮盐、芳族卤鎓盐、芳族锍盐和金属茂化合物的光引发剂。可接受的漆或基质的实例可包括Nor-Cote CDG000(UV可固化的丙烯酸酯单体和低聚物的混合物),其包含光引发剂(羟基酮)和有机溶剂丙烯酸酯(例如甲基丙烯酸甲酯、甲基丙烯酸己酯、丙烯酸β-苯氧基乙酯和丙烯酸六亚甲基酯)。其他可接受的漆或基质可包括丙烯酸酯化的聚酯低聚物如CN293和CN294,可从Sartomer公司获得。
实施例
以下实施例举例说明按照本发明实施方案制备成像溶液的特定方法。以下实施例不应该被认为是对本发明的限制,但应该被看作是基于目前实验数据的印刷介质的代表性的已知实施方案和试验。
实施例I
参考图1的实施方案,其显示一种按照本发明的实施方案制备成像溶液的方法,该方法可包括活化剂熔体10、活化剂/触角溶液20、UV可固化的漆溶液30、漆/触角/活化剂溶液40和两相UV可固化的膏剂50。在图1所举例说明的实施方案中,2克草酸二苄酯被加热至熔化(约85℃)。将20克活化剂双酚-A和1克触角IR780溶解在熔化的草酸二苄酯中。活化剂/触角溶液20被冷却并研磨成细粉70。
5克研磨的活化剂/触角粉末70溶解在15.3克Nor-Cote CDG000UV-漆30(UV可固化的丙烯酸酯单体和低聚物的混合物)中以形成漆/触角/活化剂溶液40。
10克间三联苯(促进剂)50在烧杯中熔化。熔体50被加热到110°F。在恒定搅拌下,将100克BK40055以小的增量添加到熔体。所添加的BK-400是隐色染料(2′-苯胺基-3′-甲基-6′-(二丁基氨基)荧烷),可从Nagase公司获得,其结构由以下式8所述:
(平均粒度小于约5微米)。升高混合物的温度直到170-180℃。继续搅拌直到BK400在熔体中完全溶解(通常经历10-15分钟)以形成促进剂/隐色染料溶液65。在恒定搅拌下将550mg的IR780(IR染料)70添加到熔体。IR780碘化物具有以下化学式:
加热并继续搅拌另外的约2-3分钟,直到IR染料完全溶解在熔体中以形成隐色染料/触角/促进剂合金(共晶)75。隐色染料/触角/促进剂合金75的温度保持在低于约190℃。
然后将隐色染料/触角/促进剂合金75倾入预冷却的衬有铝箔的冷冻器托盘中。固化的熔体被磨碎成粗粉并随后在水分散体中研磨直到所研磨的合金的平均粒度小于约4微米。所研磨的合金在真空中干燥以形成隐色染料共晶粉末80。
使隐色染料/触角/促进剂合金75和漆/触角/活化剂溶液40的混合物形成UV可固化的膏剂90并且以大致约5-约7微米的厚度丝网印刷到基底上形成成像介质(未示出)。然后将介质上的涂层由汞灯UV固化。
用45毫瓦激光在所得的涂层基底上直接进行标记。施加能量约30微秒-约100微秒的时间产生约20微米×45微米的标记。当期望的图像标记在成像介质上时,直接标记出现而未使用印刷媒介物。
实施例II
进行实施例I的方法,不同的是使用20克TG-SA(酚,4,4′-磺酰基双[2-(2-丙烯基)]-(9Cl))(式(9)):
作为活化剂并将1.2克触角IR780溶解在熔化的草酸二苄酯中以形成活化剂/触角溶液20,其然后被冷却和研磨成细粉70。另外,不使用100克BK400作为隐色染料55,而使用15克S-205隐色染料(2-苯胺基-3-甲基-6-(N-乙基-N-异戊基氨基)荧烷-可获自“Nagase Co.,Ltd”)(式(10)):
(平均粒度<5微米)90以形成促进剂/隐色染料溶液65。正如实施例I的情况,使隐色染料/触角/促进剂合金75和漆/触角/活化剂溶液40的混合物形成UV可固化的膏剂90并且以约7微米的厚度丝网印刷到基底上形成成像介质(未示出)。然后将介质上的涂层由汞灯UV固化。用45毫瓦激光在所得的涂层基底上直接进行标记。施加能量约60微秒-约100微秒产生约20微米×45微米的标记。
虽然本发明可能对各种变型和替换形式敏感,但具体的实施方案已经通过在附图中举例的方式进行了说明,并且在本文中已经详细阐述。然而,应当理解的是本发明不拟受限于所公开的具体形式。而是,本发明应覆盖全部的落入由以下所附权利要求所限定的本发明的精神和范围的变型、等价物和备选方案。
Claims (10)
1.一种成像组合物,其包括:
具有触角和活化剂的基质,其中所述活化剂为酚类化合物;和
作为独立相分散在所述基质中的合金,所述合金具有触角并且进一步具有均匀分布在合金中的隐色染料和促进剂,其中所述促进剂为熔融温度为50℃-150℃的芳族烃,
其中所述触角被调谐以吸收激光辐射或红外辐射,并且所述触角包括至少一种选自以下物质的化合物:醌、酞菁、萘酞菁、金属络合物、偶氮、克酮酸鎓、方形酸鎓染料、六官能聚酯低聚物和由以下化学式表示的化合物:
其中M1是过渡金属,R1、R2、R3和R4是有或者没有卤素取代基的烷基或芳基,并且A1、A2、A3和A4可为S、NH或Se;和
其中M2是Ni或Cu,R5和R6是有或者没有卤素取代基的芳基或烷基。
2.权利要求1的组合物,其中基质的触角和合金的触角是不同的化合物。
4.权利要求1的组合物,其中所述活化剂包括酚类化合物。
5.一种图像记录介质,其包括:
基底;
在基底上的基质,该基质具有触角和活化剂,其中所述活化剂为酚类化合物;和
作为独立相分散在基质中的合金,该合金具有触角并且进一步具有分布在合金中的隐色染料和促进剂,其中所述促进剂为熔融温度为50℃-150℃的芳族烃,
其中所述触角被调谐以吸收激光辐射或红外辐射,并且所述触角包括至少一种选自以下物质的化合物:醌、酞菁、萘酞菁、金属络合物、偶氮、克酮酸鎓、方形酸鎓染料、六官能聚酯低聚物和由以下化学式表示的化合物:
其中M1是过渡金属,R1、R2、R3和R4是有或者没有卤素取代基的烷基或芳基,并且A1、A2、A3和A4可为S、NH或Se;和
其中M2是Ni或Cu,R5和R6是有或者没有卤素取代基的芳基或烷基。
6.权利要求5的介质,其中基质的触角和合金的触角是不同的化合物。
7.权利要求5的介质,其中所述隐色染料包括以下结构:
其中R可为烷基、芳基或H原子。
8.一种制备成像材料的方法,该方法包括:
提供具有活化剂和触角的粉末,其中所述活化剂为酚类化合物;
溶解该活化剂/触角粉末以形成活化剂/基质预聚物溶液;
提供隐色染料合金;
将该隐色染料合金分散到该活化剂/基质预聚物溶液以形成可辐射固化的膏剂,
其中所述触角被调谐以吸收激光辐射或红外辐射,并且所述触角包括至少一种选自以下物质的化合物:醌、酞菁、萘酞菁、金属络合物、偶氮、克酮酸鎓、方形酸鎓染料、六官能聚酯低聚物和由以下化学式表示的化合物:
其中M1是过渡金属,R1、R2、R3和R4是有或者没有卤素取代基的烷基或芳基,并且A1、A2、A3和A4可为S、NH或Se;和
其中M2是Ni或Cu,R5和R6是有或者没有卤素取代基的芳基或烷基。
9.权利要求8的方法,其中提供活化剂/触角粉末包括:
熔化活化剂;
将触角溶解于活化剂中以形成活化剂/触角熔体;
冷却该活化剂/触角熔体到环境温度;和
将冷却的活化剂/触角熔体研磨成粉末。
10.权利要求8的方法,其中提供隐色染料合金包括:
提供熔融的促进剂,其中所述促进剂为熔融温度为50℃-150℃的芳族烃;
将触角溶解于熔融的促进剂中;
将隐色染料溶解于熔融的促进剂中;
冷却该隐色染料/触角/促进剂熔体至固态;和
将冷却的隐色染料/触角/促进剂熔体研磨成粉末。
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Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7700258B2 (en) * | 2003-01-24 | 2010-04-20 | Hewlett-Packard Development Company, L.P. | Color forming compositions with improved marking sensitivity and image contrast and associated methods |
US7169542B2 (en) * | 2003-10-28 | 2007-01-30 | Hewlett-Packard Development Company, L.P. | Compositions, systems, and methods for imaging |
US20050231585A1 (en) * | 2004-03-02 | 2005-10-20 | Mudigonda Dhurjati S | Method and system for laser imaging utilizing low power lasers |
US7270943B2 (en) * | 2004-07-08 | 2007-09-18 | Hewlett-Packard Development Company, L.P. | Compositions, systems, and methods for imaging |
US8153706B2 (en) | 2004-10-25 | 2012-04-10 | Hewlett-Packard Development Company, L.P. | Polymeric colorants having pigment and dye components and corresponding ink compositions |
US20060121234A1 (en) * | 2004-12-07 | 2006-06-08 | Marshall Field | Systems, compositions, and methods for laser imaging |
US7198834B2 (en) * | 2005-03-22 | 2007-04-03 | Hewlett-Packard Development Company, L.P. | Imaging media including interference layer for generating human-readable marking on optical media |
US20070015092A1 (en) * | 2005-07-13 | 2007-01-18 | Gore Makarand P | Color forming compositions |
US20070065623A1 (en) * | 2005-09-21 | 2007-03-22 | Vladek Kasperchik | Laser-imageable coating based on exothermic decomposition |
US20070065749A1 (en) | 2005-09-21 | 2007-03-22 | Vladek Kasperchik | Radiation-markable coatings for printing and imaging |
TW200713260A (en) * | 2005-09-28 | 2007-04-01 | Daxon Technology Inc | Optical disc |
US20070086308A1 (en) * | 2005-10-13 | 2007-04-19 | Gore Makarand P | Systems and methods for imaging |
US7390610B2 (en) * | 2005-10-18 | 2008-06-24 | Hewlett-Packard Development Company, L.P. | Color forming composition |
US20070105039A1 (en) * | 2005-10-18 | 2007-05-10 | Vladek Kasperchik | Dual band color forming composition |
US20070092827A1 (en) * | 2005-10-20 | 2007-04-26 | Gore Makarand P | Inks for use on light-activated imaging media |
US7935471B2 (en) * | 2005-10-20 | 2011-05-03 | Hewlett-Packard Development Company, L.P. | NIR/IR curable coatings for light directed imaging |
US7687550B2 (en) * | 2005-10-24 | 2010-03-30 | Hewlett-Packard Development Company, L.P. | Composition including a radiation-curable pre-polymer with a stabilizing additive comprising metal particles |
US20070092680A1 (en) * | 2005-10-26 | 2007-04-26 | Sterling Chaffins | Laser writable media substrate, and systems and methods of laser writing |
US7582405B2 (en) * | 2005-10-26 | 2009-09-01 | Hewlett-Packard Development Company, L.P. | Image recording media and image layers |
US7968166B2 (en) * | 2006-01-31 | 2011-06-28 | Hewlett-Packard Development Company, L.P. | Optical recording system |
US20070178271A1 (en) * | 2006-01-31 | 2007-08-02 | Gore Makarand P | Optical recording medium |
US7754413B2 (en) | 2006-03-10 | 2010-07-13 | Hewlett-Packard Development Company, L.P. | Color forming composition with enhanced image stability |
US20070243354A1 (en) * | 2006-04-18 | 2007-10-18 | Hewlett-Packard Development Company, L.P. | Image-recording medium with thermally insulating layer |
US20070248918A1 (en) * | 2006-04-25 | 2007-10-25 | Vladek Kasperchik | Compositions, systems and methods for imaging |
US8283100B2 (en) * | 2006-05-16 | 2012-10-09 | Hewlett-Packard Development Company, L.P. | Color forming compositions and associated methods |
US20080003396A1 (en) * | 2006-06-15 | 2008-01-03 | Hladik Molly L | Water-soluble coatings for media |
US20080020320A1 (en) * | 2006-07-20 | 2008-01-24 | Dorsh Cari L | Color forming composition containing optional sensitizer |
US20080090925A1 (en) * | 2006-10-13 | 2008-04-17 | Hladik Molly L | Color forming compositions |
US8506695B2 (en) * | 2006-10-25 | 2013-08-13 | Hewlett-Packard Development Company, L.P. | Coating compositions |
WO2008055244A2 (en) | 2006-10-31 | 2008-05-08 | Sensient Colors Inc. | Modified pigments and methods for making and using the same |
US8293450B2 (en) * | 2006-11-28 | 2012-10-23 | Hewlett-Packard Development Company, L.P. | Laser imaging coating and methods for imaging |
US7892619B2 (en) * | 2006-12-16 | 2011-02-22 | Hewlett-Packard Development Company, L.P. | Coating for optical recording |
EP2094498B1 (en) * | 2006-12-19 | 2012-04-04 | Hewlett-Packard Development Company, L.P. | Color forming composition containing a plurality of antenna dyes |
US7575848B2 (en) * | 2007-04-11 | 2009-08-18 | Hewlett-Packard Development Company, L.P. | Image recording media and image layers |
US7575844B2 (en) * | 2007-04-27 | 2009-08-18 | Hewlett-Packard Development Company, L.P. | Color forming composites capable of multi-colored imaging and associated systems and methods |
US7582408B2 (en) * | 2007-04-27 | 2009-09-01 | Hewlett-Packard Development Company, L.P. | Color forming compositions with a fluoran leuco dye having a latent developer |
WO2009012109A2 (en) * | 2007-07-13 | 2009-01-22 | Emory University | Cyanine-containing compounds for cancer imaging and treatment |
US7868059B2 (en) * | 2007-07-27 | 2011-01-11 | Hewlett-Packard Development Company, L.P. | Polymerizable dye-monomer conjugates for encapsulating pigment particles |
CN101855302B (zh) | 2007-08-23 | 2014-10-01 | 森馨颜色公司 | 自分散颜料及制造和使用该自分散颜料的方法 |
WO2009152440A1 (en) * | 2008-06-13 | 2009-12-17 | Cedars-Sinai Medical Center | Small molecule ligand-drug conjugates for targeted cancer therapy |
US8652607B2 (en) * | 2008-06-25 | 2014-02-18 | Hewlett-Packard Development Company, L.P. | Image recording media and imaging layers |
WO2009157924A1 (en) | 2008-06-25 | 2009-12-30 | Hewlett-Packard Development Company, L.P. | Image recording media, methods of making image recording media, imaging layers, and methods of making imaging layers |
JP2012523479A (ja) | 2009-04-07 | 2012-10-04 | センシエント カラーズ エルエルシー | 自己分散性粒子並びにその製造方法及び使用方法 |
CN105190436A (zh) | 2013-02-27 | 2015-12-23 | 富士胶片株式会社 | 红外线感光性显色组合物、红外线固化性显色组合物、平版印刷版原版和制版方法 |
JP2016539031A (ja) * | 2013-12-19 | 2016-12-15 | アグフア−ゲヴエルト | レーザーマーキング可能ラミネート及びドキュメント |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3658543A (en) * | 1970-12-18 | 1972-04-25 | Du Pont | Dual response photosensitive composition containing acyl ester of triethanolamine |
US4343885A (en) * | 1978-05-09 | 1982-08-10 | Dynachem Corporation | Phototropic photosensitive compositions containing fluoran colorformer |
JP2564642B2 (ja) | 1989-02-20 | 1996-12-18 | 日本製紙株式会社 | 光記録体 |
EP0520404B1 (en) * | 1991-06-24 | 1996-09-11 | Nippon Paper Industries Co., Ltd. | Transparent recording medium |
JPH082106A (ja) | 1994-06-24 | 1996-01-09 | Nippon Kayaku Co Ltd | マーキング用組成物及びレーザーマーキング方法 |
US5810397A (en) * | 1993-05-03 | 1998-09-22 | The Standard Register Company | Thermally imagable business record and method of desensitizing a thermally imagable surface |
US5552259A (en) * | 1993-09-23 | 1996-09-03 | Polaroid Corporation | Adhesive composition, and imaging medium comprising this adhesive composition |
US5646088A (en) * | 1995-02-16 | 1997-07-08 | Ricoh Co., Ltd. | Thermosensitive recording material and production process thereof |
US6075223A (en) * | 1997-09-08 | 2000-06-13 | Thermark, Llc | High contrast surface marking |
US6251571B1 (en) * | 1998-03-10 | 2001-06-26 | E. I. Du Pont De Nemours And Company | Non-photosensitive, thermally imageable element having improved room light stability |
US6200647B1 (en) * | 1998-07-02 | 2001-03-13 | 3M Innovative Properties Company | Image receptor medium |
US6432610B1 (en) * | 1998-09-08 | 2002-08-13 | Regents Of The University Of California | Dye precursor molecules chemically reactive with the light-altered form of light-sensitive molecules to form stable fluorescent dye, particularly for optical memories including two-photon three-dimensional optical memories |
JP3470879B2 (ja) * | 1999-01-22 | 2003-11-25 | タイホー工業株式会社 | インクジェット用被記録材用塗工剤及びインクジェット用被記録材 |
IT1309921B1 (it) * | 1999-09-03 | 2002-02-05 | Ferrania Spa | Foglio recettore per stampa a getto d'inchiostro comprendente unacombinazione di gelatina e saccaridi. |
JP3598976B2 (ja) * | 2001-01-31 | 2004-12-08 | 日本電気株式会社 | 電源ノイズセンサ |
GB0107989D0 (en) | 2001-03-30 | 2001-05-23 | Ici Plc | Improvements in or relating to inkjet printing media |
JP2003050442A (ja) * | 2001-06-01 | 2003-02-21 | Fuji Photo Film Co Ltd | 記録材料 |
JP2003076051A (ja) | 2001-08-31 | 2003-03-14 | Fuji Xerox Co Ltd | 記録用紙、及びそれを用いた画像記録方法 |
US7172991B2 (en) | 2001-10-11 | 2007-02-06 | Hewlett-Packard Development Company, L.P. | Integrated CD/DVD recording and labeling |
EP1371697A3 (en) | 2002-06-14 | 2004-01-02 | Rohm And Haas Company | Polymeric binders for inkjet inks |
GB0218505D0 (en) | 2002-08-09 | 2002-09-18 | Eastman Kodak Co | Inkjet recording medium |
US6974661B2 (en) * | 2003-01-24 | 2005-12-13 | Hewlett-Packard Development Company, L.P. | Compositions, systems, and methods for imaging |
MXPA05007805A (es) | 2003-01-24 | 2005-10-18 | Hewlett Packard Development Co | Tintes leuco negros, para su uso en etiquetar cd /dvd. |
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US7018953B2 (en) | 2006-03-28 |
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