CN114805048A - 一种碘鎓盐引发剂及包含其的免处理热敏版前体和免处理热敏版及应用 - Google Patents
一种碘鎓盐引发剂及包含其的免处理热敏版前体和免处理热敏版及应用 Download PDFInfo
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- CN114805048A CN114805048A CN202210432509.8A CN202210432509A CN114805048A CN 114805048 A CN114805048 A CN 114805048A CN 202210432509 A CN202210432509 A CN 202210432509A CN 114805048 A CN114805048 A CN 114805048A
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- iodonium salt
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- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical group [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
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- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
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- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41N—PRINTING PLATES OR FOILS; MATERIALS FOR SURFACES USED IN PRINTING MACHINES FOR PRINTING, INKING, DAMPING, OR THE LIKE; PREPARING SUCH SURFACES FOR USE AND CONSERVING THEM
- B41N1/00—Printing plates or foils; Materials therefor
- B41N1/12—Printing plates or foils; Materials therefor non-metallic other than stone, e.g. printing plates or foils comprising inorganic materials in an organic matrix
- B41N1/14—Lithographic printing foils
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
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- C07C271/48—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C09D129/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
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Abstract
本发明提供一种碘鎓盐引发剂及包含其的免处理热敏版前体和免处理热敏版及应用,该碘鎓盐引发剂在两个苯环的两个对位之中至少有一个为含有碳或氮或氧原子且末端含双键的烯烃基,该烯烃基能增加碘鎓盐的位阻,同时该烯烃基在激光成像时能参与成像层的交联反应,减低碘鎓盐分解产生的小分子对成像层的破坏。该碘鎓盐引发剂能有效地解决现有技术中鎓盐类引发剂在成像层中存在的的表面迁移和残留问题,能提升免处理热敏版、特别是含有离散颗粒的免处理热敏版的性能。
Description
技术领域
本发明属于平版印刷技术领域,具体涉及一种碘鎓盐引发剂及包含其的免处理热敏版前体和免处理热敏版及应用。
背景技术
现代印刷广泛采用计算机直接制版技术(CTP技术),常见的CTP版材分为光敏CTP版和热敏CTP版。
热敏CTP版材(简称热敏版)是一种采用红外激光进行成像的胶印版材。热敏版由于可明室操作,成像质量高而等到广泛使用。
印刷行业是对环境不友好的高污染行业,特别是印刷过程中产生的废弃显影液对环境造成很大的伤害。因此,全世界印刷业都在倡导推行绿色印刷技术。绿色印刷技术是指采用环保材料和工艺技术,减少印刷过程中产生的污染。开发是绿色环保印版是发展绿色印刷的重中之重。
热敏版技术在不断地进步和发展,热敏版材也在更新换代,其中技术发展方向之一就是探索绿色印刷技术,开发环境友好的免处理热敏版。
免处理热敏版技术路线很多,可分为热烧蚀技术、相变技术和热熔技术等等。热烧蚀技术指红外激光能量烧蚀亲油涂层,露出铝版亲水表面形成亲水区;相变技术指激光能量使聚合物发生亲水亲油转换,实现墨、水分离;热熔技术是激光能量使分散在交联亲水层中的热塑性聚合物颗粒融化,由亲水性变成疏水亲油性。
免处理热敏版可分为两大类:(1)直接上机免处理热敏版。版材成像后可以直接上机,在印刷机润版液作用下进行显影、印刷,;(2)低化学显影型免处理热敏版。版材在制版机上曝光成像后,不需要化学显影液,采用清水清洗即实现可显影,然后上机印刷。
开发免处理热敏版、特别是开发免处理热敏版的前体,是当今世界开发免处理热敏版的热点。免处理热敏版的前体是指制造免处理热敏版的前驱体,泛指制造免处理热敏版前所需的必要材料和技术。
开发免处理热敏版前体的技术:WO2013/032780公开了一种用于在机显影的平版印版前体;EP0980754介绍了脱羧实现亲水疏水转变技术;WO94/23954介绍了热熔使微胶技术;US4004924介绍一种热塑性疏水颗粒和亲水粘结剂的混合体;EP 2006-5-2406114475.4介绍一种热熔热塑性颗粒;US 2005-8-3 11/196,124介绍一种一维线性结构亲水性的粘合剂;US 2006-7-27 11/494,235介绍一种含亲水基和酯化烯丙基印版前体等等。
目前免处理热敏版材采用的技术很多,其中主流技术之一就是利用激光的热作用于引发剂,引发剂触发热敏层产生化学反应,实现激光成像。其中,鎓盐类引发剂被广泛应用于免处理热敏版材的激光成像体系中。
在免处理热敏版技术不断发展、提高的过程中,技术人员发现,鎓盐类引发剂用于免处理热敏版材的激光成像体系中存在如下急需解决难题:1、鎓盐类引发剂在成像层中的表面迁移问题。鎓盐类引发剂在成像层中的表面迁移问题直接影响引发效率,造成深层引发不足,图像网点还原不真实、涂层不牢固等问题;2、激光分解后的鎓盐类引发剂产生的小分子对成像层的破坏。上述问题在成像层中含有离散颗粒的免处理热敏版材中尤为明显。
为了解决述鎓盐类引发剂在成像层中存在的的表面迁移和残留问题,提高引发效率,进一步提升免处理热敏版的性能,是本发明的目的。
发明内容
为解决上述问题,本发明提供一种碘鎓盐引发剂及包含其的免处理热敏版前体和免处理热敏版及应用,该碘鎓盐引发剂在两个苯环的两个对位之中至少有一个为含有碳或氮或氧原子且末端含双键的烯烃基,该烯烃基能增加碘鎓盐的位阻,同时该烯烃基在激光成像时能参与成像层的交联反应,减低碘鎓盐分解产生的小分子对成像层的破坏。该碘鎓盐引发剂能有效地解决现有技术中鎓盐类引发剂在成像层中存在的的表面迁移和残留问题,能提升免处理热敏版、特别是含有离散颗粒的免处理热敏版的性能。
本发明的目的是以下述方式实现的:
本发明所述的一种碘鎓盐引发剂是一种阳离子引发剂,具体地说是一种含有双键的大分子碘鎓盐,具有如下结构:
其中:
R1、R2为H,或为1-12个碳原子的烷基,或为含有碳或氧或氮原子且末端含双键的烯烃基,并且R1、R2之中至少有一个为含有碳或氮或氧原子且末端含双键的烯烃基,
R3、R4、R5、R6独立的为H或1-12个碳原子的烷基,
X-为酸根阴离子,优选的,X-为六氟磷酸根阴离子、六氟锑酸根阴离子或四氟硼酸根阴离子。
一种免处理热敏版前体,包括载体、成像层,成像层包括亲水热敏树脂、可交联预聚体、热引发剂和红外吸收剂;热引发剂为本申请所提供的上述结构的碘鎓盐引发剂。
本发明提供的碘鎓盐引发剂是一种含有双键的大分子碘鎓盐,在两个苯环的两个对位之中至少有一个为含有碳或氮或氧原子且末端含双键的烯烃基,该烯烃基能增加碘鎓盐的位阻,提高碘鎓盐和热敏树脂、可交联预聚体的相融性,减少碘鎓盐在成像层中的表面迁移,提高引发效率;激光成像时,碘鎓盐残端含有的双键可以和热敏树脂、交联预聚体发生交联反应,减少小分子的产生对成像层的破坏;同时可以选择在两个苯环的四个间位可以设置取代基增加碘鎓盐的位阻,进一步减少碘鎓盐在成像层中的表面迁移,提高引发效率,进一步达到提升免处理热敏版性能目的。
具体实施方式
本发明所述的一种碘鎓盐引发剂是一种阳离子引发剂,具体地说是一种含有双键的大分子碘鎓盐,具有如下结构:
其中:
R1、R2为H,或为1-12个碳原子的烷基,或为含有碳或氧或氮原子且末端含双键的烯烃基,并且R1、R2之中至少有一个为含有碳或氮或氧原子且末端含双键的烯烃基,
R3、R4、R5、R6独立的为H或1-12个碳原子的烷基,
X-为酸根阴离子,优选的,X-为六氟磷酸根阴离子、六氟锑酸根阴离子或四氟硼酸根阴离子。
一种免处理热敏版前体,包括载体、成像层,成像层包括亲水热敏树脂、可交联预聚体、热引发剂和红外吸收剂;热引发剂为本申请所提供的上述结构的碘鎓盐引发剂。
本申请结构的碘鎓盐引发剂在激光热的作用下能发生均裂和异裂,能同时产生自由基和亲电的质子酸,使得热敏树脂和可交联预聚体发生自由基聚合和阳离子聚合,实现激光成像。
本发明的碘鎓盐的X-为鎓盐反离子,鎓盐反离子包括酸根阴离子,如氯离子等卤素阴离子、硫酸根、对甲苯磺酸根、六氟磷酸根、六氟锑酸根、四氟砷酸根等等。本发明所述的鎓盐反离子优选六氟磷酸根、六氟锑酸根、四氟砷酸根。
具有本发明所述结构的大分子碘鎓盐(代号D),可以列举的具体例子如下(不仅限于此):
D1:
D2:
D3:
D4:
D5
D6:
D7
D8:
D9:
D10:
D11:
D12:
D13:
D14
D15
D16
D17:
D18
D19
D20
D21
D22:
D23:
成像层中的热引发剂,按重量百分比计占组成物固体总量的1-10%。
下面描述成像层中的亲水热敏树脂:
免处理热敏版成像层中需要一种高分子树脂,具体而言,它是一种带有功能基团的高分子成膜树脂。本发明的成像层中的亲水热敏树脂就是一种功能性成膜树脂,这种高分子树脂除了要具备成膜性,能保证成像层涂布液干燥后成膜附着在载体上外,还要具备亲水和热敏感的特殊的功能。
本发明的免处理热敏版前体中所述的亲水热敏树脂为支链含有亲水基和环氧基的聚烯烃树脂。更进一步,本发明的免处理热敏版前体中所述的亲水热敏树脂为共聚链上至少含有聚醚类丙烯酸酯或丙烯酰胺类亲水共聚单元和环氧类丙烯酸酯共聚单元的聚烯烃树脂。
作为免处理热敏版成像层中的主体树脂,它首先要具备亲水性,激光成像时,未交联部分能实现水或含有树胶的水简单预清洁,或在机印刷在润版液的作用下实现清洁,露出亲水版基,而受激光热作用后交联成像部分由于亲水树脂和预聚体交联形成三维网状结构,树脂的极性和溶解性改变,由亲水转变为疏水。实现树脂水溶性的最好办法就是直接选择具有亲水侧基的乙烯基单体作为树脂的共聚单元。亲水侧基有羧基、羟基、磷酸基、磺酸基、氨基、酰胺基、醚基等等。本发明的亲水热敏树脂选用支链聚醚或酰胺基作为亲水基,即亲水热敏树脂为共聚链上至少含有聚醚类丙烯酸酯或丙烯酰胺类亲水共聚单元。聚醚类丙烯酸酯或丙烯酰胺类亲水共聚单元赋予亲水热敏树脂良好的自乳化性,能使亲水热敏树脂形成纳微米热塑性颗粒状态,同时聚醚基和丙烯酰胺具有良好的耐溶剂性,可以抵抗UV油墨中的单体对成像层的浸蚀。
另外,作为免处理热敏版成像层中的主体树脂,树脂最好含有对热敏感的基团,有助于热敏成像。这类成像基团可以是能发生自由基聚合的双键或能发生阳离子聚合的环氧基等等。本发明的亲水热敏树脂含有对热敏感的基团,选用能发生阳离子聚合的环氧基作为光敏基团,所以在树脂结构单元上含有环氧类丙烯酸酯共聚单元,可以优先甲基丙烯酸缩水甘油酯、3,4-环氧环己基甲基丙烯酸酯等环氧类丙烯酸单体,进一步可以优先含有环己基的环氧类丙烯酸单体,如3,4-环氧环己基甲基丙烯酸酯,环己己可以较好的刚性,而且环己基上的环氧基具有非常高的阳离子聚合的活性。
最后,作为免处理热敏版成像层中的主体树脂,还需考虑树脂的刚性、亲墨性等综合性能。当树脂为纳微米颗粒状态作为免化学处理热敏版的粘合剂时,树脂最好含有热塑性结构单元,有利于激光热熔成膜。本发明的亲水热敏树脂优选苯乙烯结构单元。众所周知,苯乙烯结构单元具有良好的热塑性,玻璃转化温度较高,苯乙烯共聚物作为免化学处理热敏CTP版粘合剂具有受热部分更容易热熔,分子之间排列更为紧密,热影像部分更为牢固,能增加版材耐印力的优点。
免处理热敏版成像层中亲水热敏树脂的形态可以是固体状体、溶液状态或者是乳液状态等等。优选为离散颗粒状态,热敏成像时激光能使离散颗粒状态的热塑性聚合物颗粒的温度发生凝集反应,曝光区由亲水性变成疏水亲油性。
合成本发明所述的亲水热敏树脂采用溶液或乳液共聚的方法,共聚反应可选无规共聚或嵌段共聚,优选无规共聚。聚合的引发剂包括过氧化物如二叔丁基过氧化物、苯甲酰基过氧化物,过硫酸盐如过硫酸钾、过硫酸胺,偶氮化合物如偶氮二异丁腈等,共聚方式优选乳液聚合。
可选用的反应溶剂有水、醇类、酮类、酯类、醚类等溶剂或者是它们的混合物。共聚反应温度优选40-100℃,最优为60-90℃。
本发明的免处理热敏版前体,其中所述的亲水热敏树脂可以优选苯乙烯、聚乙二醇丙烯酸酯(分子量为2000)、异丙基丙烯酰胺和3,4-环氧环己基甲基丙烯酸酯共聚得到的聚烯烃树脂,亲水热敏树脂中共聚单元按重量百分比计算,苯乙烯占30-70%、聚乙二醇甲醚甲基丙烯酸酯(数均分子量Mn=2000)占5-20%、异丙基丙烯酰胺占5-20%、3,4-环氧环己基甲基丙烯酸酯占10-30%。状态为粒径为50-200nm的离散颗粒。
成像层中的亲水热敏树脂,按重量百分比计占组成物固体总量的40-80%,
下面描述成像层中的可交联预聚体:
成像层中的可交联预聚体可以是能发生自由基聚合的单体或能发生阳离子聚合的单体等等。自由基聚合的单体一般为含有双键的丙烯酸类单体,能发生阳离子聚合的单体一般为含有环氧基的单体。本发明所述成像层中的可交联预聚体为多官能度丙烯酸类单体或多官能度聚氨酯丙烯酸类单体,这里多官能度的含义是指是指它含有多个双键。多官能度丙烯酸类单体如1,6-己二醇二丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、五丙烯酸二季戊四醇酯、三羟甲基丙烷三丙烯酸酯、羟丙基甘油基三丙烯酸酯、羟乙基三羟甲基丙烷三丙烯酸酯、聚乙二醇二甲基丙烯酸酯、二季戊四醇六丙烯酸酯等;多官能度聚氨酯丙烯酸类单体为异氰酸酯和多官能度丙烯酸酯缩合的产物,如异氰酸酯与羟乙基丙烯酸酯和季戊四醇三丙烯酸酯缩合的产物等;或者是含双键的异氰酸酯如甲基丙烯酰氧异氰酸酯和多羟基化合物如季戊四醇缩合的产物。
成像层中的可交联预聚体,按重量百分比计占组成物固体总量的10-50%。
下面描述成像层中的红外吸收剂:
本发明成像层中的红外吸收剂主要起能量转移的作用,红外激光的热量通过红外吸收剂将激光能量传递给热引发剂,热引发剂裂解产生活性基使亲水热敏树脂和可交联预聚体发生三维网状聚合,实现热敏成像。红外吸收剂的最大吸收波长范围为750-1100nm,选自碳黑、偶氮染料、三芳胺染料、吲哚鎓染料、氧杂菁染料、花青染料、份菁染料、吲哚菁染料、酞菁染料、聚噻吩染料、吡唑啉偶氮染料、噁嗪染料、萘醌染料、蒽醌染料、醌亚胺染料、次甲基染料、卟啉染料等等。为了提高制版反差,有利于印刷操作工肉眼校版检测印版的图像弊病,同时有利于现代的高度智能化的印刷机通过版材四个角的十字线图像自动定位识别实现了自动智能装版。选用的红外吸收剂可以选择具有变色功能的红外吸收剂,通过激光裂解实现高反差图像的呈现。本发明成像层中的红外吸收剂优选为750-850nm的菁染料。
本发明成像层中的红外吸收剂,按重量百分比计占组成物固体总量的1-10%。
下面详述本发明免处理热敏版前体中的载体。
本发明成像层需涂布到载体上,载体包括金属版基如钢基、铜基、铝基等等金属版基本发明所选的载体为经过电解粗化、阳极氧化后的铝版基。
铝版基通过电解粗化制得,中心线平均粗度0.3-0.6um。采用铝99%以上,铁占0.1%-0.5%、硅占0.03%-0.3%、铜占0.003%-0.03%,钛占0.01%-0.l%的铝版基,电解粗化电解液可以是酸、碱或盐的水溶液。首先把铝版放在1%-30%的氢氧化钠、氢氧化钾、碳酸钠、硅酸钠等的水溶液中,在20-80℃的温度5-250秒化学腐蚀。然后在10%-30%的硝酸或硫酸中以20-70℃的温度中和,去除灰质。在10-60℃的温度下,用正负性交互变化的矩形波、台型波或正弦波等,以5-100A/dm2的电流密度,在硝酸或者盐酸的电解液中电解处理10-300秒。电解粗化和阳极氧化处理的铝版基接着进行阳极氧化处理。阳极氧化通常用硫酸法,使用的硫酸的浓度为5-30%,电流密度为1-15A/dm2,氧化温度在20-60℃,氧化时间为5-250秒,以形成1-10g/m2的氧化膜,最后封孔处理。电解粗化和阳极氧化处理的铝版基可以选择或不选择进行封孔处理,封孔处理可以使用各种各样的方法,以封闭氧化膜微孔的50-80%体积为佳,例如在经过上述处理的铝板上涂敷厚度为3mg/m2聚乙烯基膦酸封闭氧化膜微孔。
本发明的免处理热敏版前体可以用来制造免处理热敏版,制造的免处理热敏版步骤至少包括载体处理和成像层涂布。还可以选择或不选择涂布保护层。在成像层上再涂布一层保护层,减少氧气产生阻聚效应影响热敏版成像层的性能,同成像层不被外界环境污染、划伤作用。保护层可以采用结晶性比较优良的水溶性高分子化合物,如聚乙烯醇、聚乙烯吡咯烷酮、羟丙基纤维素、明胶、阿拉伯树胶、聚丙烯酸等水溶性聚合物。
使用本发明的免处理热敏版前体制造的免处理热敏版时还可以加入包括一些其它必要的助剂,如溶剂、常温热聚合抑制剂、表面活性剂、图层着色剂等等。溶剂主要是为了把热敏组合物配制热敏涂层感光液,包括:醇类、酮类、酯类、醚类、酰胺类、芳香类溶剂以及二氯化乙烯、四氢呋喃等,溶剂可以以纯的或混合物形式使用;常温热聚合抑制剂是为了防止板材在常温下发生聚合,提高版材的常温稳定性。热聚合抑制剂包括:氢醌、氮氧自由基哌啶醇、对甲氧基苯酚、二叔丁基对甲酚、连苯三酚、叔丁基儿茶酚、苯醌、4,4'-硫代双-(3-甲基-6-叔丁基苯酚)、2,2’-亚甲基双(4-甲基-16-叔丁基苯酚),以及N-亚硝基苯基羟基胺的伯铈盐等等;加入图层着色剂是为了增加热敏版制版后的图像密度,便于对制版后热敏版进行目测检查或图像分析测量设备测量版材性能,它包括:甲基紫、乙基紫、结晶紫、结晶内紫、维多利亚蓝、油绿、油蓝、油黄、若丹明B、甲基紫罗兰、孔雀石绿、亚甲基蓝、三嗪类等等;涂层还需加入表面活性剂,可选用非离子表面活性剂、两性表面活性剂、含硅表面活性剂、含氟表面活性剂等,如甜菜碱类、硬脂酸甘油酯类、山梨酸棕油酯类、聚硅氧烷类、聚氟烷基醚类。
使用本发明的免处理热敏版前体制备的免处理热敏版通常用该领域己知技术涂布(如,刀涂,刮涂,条涂,辊涂,压涂等)。
使用本发明的免处理热敏版前体制造的免处理热敏版使用热敏CTP制版机扫描曝光后,经过水冲洗显影后或直接装版到印刷机上经印刷机润版液显影、印刷。
下面结合具体实施例对本发明进行具体描述,有必要在此指出的是本实施例只用于对本发明进行进一步说明,不能理解为对本发明保护范围的限制,该领域的技术熟练人员可以根据上述本发明的内容做出一些非本质的改进和调整。
下面是本发明的合成实例,但本发明并不局限于下述实例。
第一部分:引发剂合成实例(D1-D23均由乐凯华光合成,以下是合成基本路线)。
主要原材料可以从以下公司获得:四水合硼酸钠、氯化铵、碘酸钾、氯化钡来自上海百灵威科技,浓硫酸(质量分数为98%)、乙酸、乙酸酐、环己酮、甲醇来自开封试剂有限公司,4-N(烯丙基)-3,5-二异丙基碘苯、3,5-二甲基-4-叔丁基对碘苯来自沈阳化工研究院,N-(丙烯酸乙酯)-2,6-二甲基-苯甲酸、(甲基丙烯酸羟丙酯取代)异丙基-2,6-二甲基苯和N-(丙烯酰氧基)-2,6-二甲基苯来自乐凯华光,六氟磷酸钾、四氟硼酸钾、六氟锑酸钾来自天津博迪化工有限公司,乙醚、石油醚来自天津化学试剂二厂。
不对称大分子碘鎓盐合成实例:
碘鎓盐D13的合成:
在500ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加23g四水合硼酸钠、40g乙酸、60g乙酸酐,在30℃下搅拌1.5小时,然后加入58.2g 3,5-二甲基-4-叔丁基对碘苯,在40℃下搅拌1.5小时,然后降温至0℃,然后加入43.4g N-(丙烯酸乙酯)-2,6-二甲基-苯甲酸,温度控制5℃以下,滴加30ml浓硫酸和30ml乙酸的混合液,升温至15℃搅拌24小时,将反应液倒入冰水中搅拌0.5小时,用石油醚萃取3次,然后向水相中慢慢滴加质量分数为20%的氯化铵水溶液1000ml,析出固体、过滤、去离子水洗涤、真空干燥,然后将所得固体溶于甲醇中,加入30g氟硼酸钾反应2小时,反应液去离子1000ml去离子水中,过滤收集析出的固体,去离子水洗涤,真空干燥获得目标产物D13。
碘鎓盐D16的合成:
在500ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加23g四水合硼酸钠、40g乙酸、60g乙酸酐,在30℃下搅拌1.5小时,然后加入43.4g 4-N(烯丙基)-3,5-二异丙基碘苯,在40℃都下搅拌1.5小时,然后降温至0℃,然后加入53g N-(丙烯酸乙酯)-2,6-二甲基-苯甲酸,温度控制5℃以下,滴加30ml浓硫酸和30ml乙酸的混合液,升温至15℃搅拌24小时,将反应液倒入冰水中搅拌0.5小时,用石油醚萃取3次,然后向水相中慢慢滴加质量分数为20%的氯化铵水溶液1000ml,析出固体、过滤、去离子水洗涤、真空干燥,然后将所得固体溶于甲醇中,缓慢滴入质量分数为10%的六氟磷酸钾水溶液400ml,过滤收集析出的固体,去离子水洗涤,真空干燥获得目标产物D16。
对称大分子碘鎓盐合成实例:
碘鎓盐D17的合成:
在500ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加碘酸钾47.1g、N-(丙烯酸乙酯)-2,6-二甲基-苯甲酸78g、冰乙酸200ml、乙酸酐100ml,冰水浴中下搅拌,缓慢滴加浓硫酸40ml和乙酸60ml的混合液,反应6小时,然后升温至15℃搅拌24小时,过滤不溶物,加入乙醚500g和水500g的混合液,取水相,再用乙醚200ml萃取2次,取水相,加去离子水稀释至1000ml,缓慢滴入质量分数为10%的六氟磷酸钾水溶液400ml,过滤收集析出的固体,去离子水和乙醚交替洗涤2次,真空干燥获得目标产物D17。
碘鎓盐D19的合成:
在1000ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加碘酸钾47.1g、2,6-二甲基-N-(丙烯酸乙酯)-苯甲酸78g、氯化钡21g、冰乙酸200ml、乙酸酐100ml、冰水浴中下搅拌,缓慢滴加浓硫酸40ml和乙酸60ml的混合液,反应6小时,然后升温至15℃搅拌24小时,过滤不溶物,加入环己酮200ml和40g六氟锑酸钾,反应2小时,反应液滴入1000ml去离子水中,过滤收集析出的固体,去离子水洗涤2次,真空干燥获得目标产物D19。
参照上述合成基本路线,合成大分子碘鎓盐D1-D23。
第二部分:亲水热敏树脂合成实例(编号A1-A22)。
主要原材料可以从以下公司获得:苯乙烯St、异丙基丙烯酰胺IPAM、异丙醇来自上海百灵威科技;聚乙二醇甲醚甲基丙烯酸酯PEGMA(数均分子量Mn=2000)来自默克化学Sigma-Adrich;3,4-环氧环己基甲基丙烯酸酯CMA来自日本三菱丽阳化学株式会社;甲乙酮MEK:兰州石化,偶氮二异丁氰AIBN:天津福晨化学试剂。
亲水热敏树脂A1:在500ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加75g去离子水、250g异丙醇,升温至80℃开始滴加下列混合液:30g(30重量%)苯乙烯St、20g(20重量%)聚乙二醇甲醚甲基丙烯酸酯PEGMA(数均分子量Mn=2000)、20g(20重量%)异丙基丙烯酰胺IPAM、30g(30重量%)3,4-环氧环己基甲基丙烯酸酯、1g偶氮二异丁腈,滴加时间60分钟,然后80℃下反应8小时,补加入0.51g偶氮二异丁腈再继续反应8小时后降温结束反应,测得粒径50nm。反应原液按含固量直接使用。
按照表1给出的共聚单元比例,参照亲水热敏树脂A1合成工艺,调整水、醇用量以及滴加时间,合成不同共聚单元比例和粒径的亲水热敏树脂A1-A22,粒径见表1。
合成本发明的亲水热敏树脂的比较例亲水热敏树脂:
按照爱克发专利EP 2006-5-24 06114475.4介绍,合成爱克发聚合物F,聚合物不含化亲水性基团,聚合物结构:
基本操作:在1000ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加75g去离子水、250g异丙醇,、5g十二烷基硫酸钠,80℃下滴加60g(60重量%)St(苯乙烯)、40g(40重量%)AN(丙烯腈)、0.7g AIBN(偶氮二异丁腈),滴加时间0.5小时,再反应7.5小时后补加0.3g AIBN(偶氮二异丁腈),继续再反应12小时后结束。
按照柯达专利US 2005-8-3 11/196,合成柯达聚合物K,聚合物含聚醚亲水性基团,但不含环氧基,聚合物结构:
基本操作:在1000ml带温控加热、机械搅拌、冷凝回流和氮气保护装置的四口烧瓶中加75g去离子水、250g正丙醇,80℃下滴加20g(20重量%)St(苯乙烯)、70g(70重量%)AN(丙烯腈)、10g(10重量%)PEGMA(聚乙氧基甲基丙烯酸酯)、AIBN(偶氮二异丁腈),滴加时间0.5小时,再反应7.5小时后补加0.3g AIBN(偶氮二异丁腈),继续再反应12小时后结束。
实施例1
版基的制备:纯度99.5%、厚0.3mm的A1050压延铝版,在质量分数为5%的氢氧化钠水溶液中70℃下浸蚀20秒,用流水冲洗后,立即用质量分数为1%的硝酸水溶液中和。然后在质量分数为1%的盐酸水溶液中,40℃下用正弦波交流电以50A/dm2的电流密度电解粗化16秒,接着40℃下,用质量分数为5%的氢氧化钠水溶液中和10秒,水洗。最后在30℃下,用质量分数为20%的硫酸水溶液,以15A/dm2的电流密度,阳极氧化20秒,水洗。80℃下用质量分数为5%的硅酸纳水溶液进行封孔处理18秒,水洗,干燥,这样得到的版基,中心线平均粗度为0.5μm,氧化膜重3.0g/dm2。
成像层原料:符合本发明要求的红外吸收剂可以从Dye Chemical或Merck公司获得,示例中红外吸收剂(IR820)为Merck公司产品Sigma-Adrich543365,化学名:2-[2-[2-氯-3-[[1,3-二氢-1,1-二甲基-3-(4-磺酸丁基)-2H-苯并[e]吲哚-2-亚基]-亚乙基]-1-环己烯-1-基]-乙烯基]-1,1-二甲基-3-(4-磺酸丁基)-1H-苯并[e]吲哚鎓氢氧化物内盐;多官能度丙烯酸酯:SR399为二季戊四醇五丙烯酸酯,来至沙多玛;多官能度聚氨酯丙烯酸酯:PU100为聚氨酯丙烯酸酯,是科思创Desmodurn100和丙烯酸羟乙酯、季戊四醇三丙烯酸酯缩聚物,从沈阳化工研究院获得;表面活性剂BYK306来至BYK公司;1-甲氧基-2-丙醇来至联碳化学;聚乙烯醇PVA-205来至日本可乐丽株式会社;聚乙烯吡咯烷酮PVPK30来至德国BASF;乳化剂OP-10来至德国汉姆。
成像层原料(具体原料和用量如表2):
亲水热敏树脂
可交联预聚体
热引发剂
红外吸收剂(IR820)
将上述原料加入0.5g表面活性剂BYK306,1-甲氧基-2-丙醇700g配置成成像层涂布液,在上述经过亲水化处理的版基上挤压涂布成像层涂布液,在100℃下干燥60秒。得到15mg/dm2的涂层干重。
在成像层上挤压涂布下述的保护层,然后在110℃下干燥60秒。得到10mg/dm2的涂层干重。
保护层配方:
用上面相同的工艺制备不同的热敏版:版基、保护层、溶剂等必要添加剂不变,按照表2给出的数据改变成像层配方,制作实施例1-22和比较例热敏版1-12,其性能列于后面的表3中。
版材的测试分析:
初始:指版材刚制造出来的时候;
强制老化:以强制的方式模拟自然存放的状态;
1、初始感度:感度是以成像时需要的激光能量值表征,刚生产出来的版材如果引发效率越低,激光成像需要的能量越高;将上述刚生产的所有版材在Kodak全胜热敏CTP制版机上,以5mJ/cm2的递进量,在80-200mJ/cm2的能量范围内进行曝光,按照PantoneLIVE色彩数字工作流程,测定其版材的初始感度,其性能列于后面的表3中。
2、初始网点质量:网点质量是以激光成像后1-99%的网点是否都能来表征的,例如1-99%代表1%的网点到99%的网点均能还原,这是最佳值,2-98%代表仅能还原2-98%的网点,1%和99%的网点不能还原,稍差,依此类推。刚生产出来的版材如果引发效率越低,就不能完全还原1-100%的网点高。将上述所有版材在Kodak全胜热敏CTP制版机上以最佳感度的能量进行曝光,按照PantoneLIVE色彩数字工作流程,测定其图像初始网点还原值,其性能列于后面的表3中。
3、强制老化感度:强制老化是模拟热敏版在自然存放条件保质期内的变化,将上述所有版材放入标准热敏版产品包装盒内,在40℃、80%湿度的老化箱里强制老化5天后。然后在Kodak全胜热敏CTP制版机上,以5mJ/cm2的递进量,在80-200mJ/cm2的能量范围内进行曝光,按照PantoneLIVE色彩数字工作流程,测定其版材的感度,其性能列于后面的表3中。
4、强制老化网点质量:将上述所有版材放入标准热敏版产品包装盒内,在40℃、80%湿度的老化箱里强制老化5天后,然后在Kodak全胜热敏CTP制版机上以最佳感度的能量进行曝光,按照PantoneLIVE色彩数字工作流程,测定其图像网点还原值,其性能列于后面的表3中。
5、迁移评级:将上述所有版材放入标准热敏版产品包装盒内,在40℃、80%湿度的老化箱里强制老化7天后,热引发剂迁移到版材表面,和刚制作的敏版相比较,表观会产生差异,采用爱色丽(X.rite)彩通eXact扫描分光光度仪,按照PantoneLIVE色彩数字工作流程对热敏版表观质量进行分析评级,获得迁移值,10分制评分,分为1-10分,10分为最差,1分为最好。
6、耐印力:如果碘鎓盐引发效率低,成像层固化不充分,将降低版材的耐印力;另外,如果碘鎓盐在成像层中产生表面迁移,激光曝光同时还产生小分子破化成像层结构,也大大降低版材的耐印力。使用Heidelberg-XL754C印刷机上机印刷,测试热敏版印刷出正常印品的总印张数,其性能列于后面的表3中。
由表3的检测应用结果表明,与其它免处理版材相比较,本发明的免处理热敏版前体制造的热敏版具有优良的成像性能、稳定性和耐印力,这是因为本发明的免处理热敏版前体中的热引发剂是一种含有双键的大分子碘鎓盐,在两个苯环的两个对位之中至少有一个为含有碳或氮或氧原子且末端含双键的烯烃基,该烯烃基能增加碘鎓盐的位阻,提高碘鎓盐和热敏树脂、可交联预聚体的相融性,减少碘鎓盐在成像层中的表面迁移,提高引发效率;激光成像时,碘鎓盐残端含有的双键可以和热敏树脂、交联预聚体发生,减少小分子产生对热敏涂层的破坏;同时可以选择在两个苯环的四个间位可以设置取代基增加碘鎓盐的位阻,减少碘鎓盐在成像层中的表面迁移,提高引发效率,达到提升免处理热敏版性能目的。
表1亲水热敏树脂合成重量百分比投料及颗粒粒径表
表2实施例和比较例版材成像层投料表(单位:克)
表3版材应用性能表
以上所述的仅是本发明的优选实施方式,但本发明的保护范围并不局限于此,应当指出,对于本领域的及任何熟悉本技术领域的技术人员来说,在不脱离本发明整体构思前提下,根据本发明的技术方案及其发明构思加以等同替换或改变,及作出的若干改变和改进,这些也应该视为本发明的保护范围。
Claims (14)
2.根据权利要求1所述的碘鎓盐引发剂,其特征在于:X-为六氟磷酸根阴离子、六氟锑酸根阴离子或四氟硼酸根阴离子。
3.根据权利要求1所述的碘鎓盐引发剂,其特征在于:1-12个碳原子的烷基为甲基、乙基、异丙基、叔丁基或十二烷基。
4.根据权利要求1所述的碘鎓盐引发剂,其特征在于:所述的含有碳或氧或氮原子且末端含双键的烯烃基为通过亚甲基、酯基、酰胺基连接的末端双键烯烃。
5.一种免处理热敏版前体,包括载体和成像层,其特征在于:成像层包括亲水热敏树脂、可交联预聚体、热引发剂和红外吸收剂;热引发剂为权利要求1-4任一权利要求所述的碘鎓盐引发剂。
6.根据权利要求5所述的免处理热敏版前体,其特征在于:成像层按重量百分比计,亲水热敏树脂占组成物固体总量的40-80%,可交联预聚体占组成物固体总量的10-50%,热引发剂占组成物固体总量的1-10%,红外吸收剂占组成物固体总量的1-10%。
7.根据权利要求5所述的免处理热敏版前体,其特征在于:成像层上还设有保护层。
8.根据权利要求5-7任一权利要求所述的免处理热敏版前体,其特征在于:亲水热敏树脂为支链含有亲水基和环氧基的聚烯烃树脂;可交联预聚体为为多官能度丙烯酸类单体或多官能度聚氨酯丙烯酸类单体。
9.根据权利要求8所述的免处理热敏版前体,其特征在于:亲水热敏树脂为共聚链上至少含有聚醚类丙烯酸酯或丙烯酰胺类亲水共聚单元和环氧类丙烯酸酯共聚单元的聚烯烃树脂。
10.根据权利要求8所述的免处理热敏版前体,其特征在于:亲水热敏树脂为苯乙烯、聚乙二醇甲醚甲基丙烯酸酯(数均分子量Mn=2000)、异丙基丙烯酰胺和3,4-环氧环己基甲基丙烯酸酯共聚得到的聚烯烃树脂;按重量百分比计算,苯乙烯占30-70%、聚乙二醇甲醚甲基丙烯酸酯(数均分子量Mn=2000)占5-20%、异丙基丙烯酰胺占5-20%、3,4-环氧环己基甲基丙烯酸酯占10-30%。
11.根据权利要求5所述的免处理热敏版前体,其特征在于:亲水热敏树脂状态为粒径为50-200nm的离散颗粒。
12.根据权利要求5所述的免处理热敏版前体,其特征在于:红外吸收剂为吸收峰在750-850nm的菁染料,载体是经过电解粗化和阳极氧化处理的铝版基。
13.一种免处理热敏版,其特征在于:由权利要求5-12任一权利要求所述的免处理热敏版前体制备而成。
14.根据权利要求13所述的免处理热敏版的应用,其特征在于:该热敏版在使用热敏CTP制版机扫描曝光后,经过水冲洗显影后装版到印刷机上印刷或直接装版到印刷机上经印刷机润版液显影、印刷。
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