CN108699314B - 光固化性树脂组合物、油墨和涂料 - Google Patents
光固化性树脂组合物、油墨和涂料 Download PDFInfo
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- CN108699314B CN108699314B CN201780014338.4A CN201780014338A CN108699314B CN 108699314 B CN108699314 B CN 108699314B CN 201780014338 A CN201780014338 A CN 201780014338A CN 108699314 B CN108699314 B CN 108699314B
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Abstract
本发明的目的在于,提供:能构成印刷适合性优异的组合物的光固化性树脂组合物。本发明涉及一种光固化性树脂组合物,其特征在于,含有:将下述通式(I)所示的烯丙基系化合物聚合而得到的烯丙基系聚合物(A);和,胶凝剂(B)[通式(I)中,R1和R2分别表示H或CH3,X表示不具有取代基的饱和或一部分不饱和的四元~八元环的环状骨架、且为a价的基团,a表示2或3。]。
Description
技术领域
本发明涉及含有烯丙基系聚合物(A)和胶凝剂(B)的光固化性树脂组合物、以及包含该树脂组合物而成的油墨、涂料。更详细而言,涉及印刷适合性优异的光固化性树脂组合物。
背景技术
以往,利用光(例如紫外线)而固化的各种树脂组合物在油墨、涂料、粘接剂、光致抗蚀剂等中使用。例如,紫外线固化型的印刷油墨在因固化速度快而能够短时间内固化、因不使用溶剂而适于环境、节约资源·节约能源等方面有较高评价,实用化正在推进。
这样的树脂组合物中,含有由苯二甲酸二烯丙酯(邻苯二甲酸二烯丙酯、间苯二甲酸二烯丙酯、对苯二甲酸二烯丙酯)衍生的苯二甲酸二烯丙酯树脂的树脂组合物作为纸用的UV胶版油墨采用。
专利文献1中记载了活性能量射线固化型印刷油墨用凝胶清漆,其将含有A.铝醇盐或铝螯合化合物、B.苯二甲酸二烯丙酯预聚物和C.与B相容的活性能量射线固化性液态化合物的混合物加热而得到,虽然印刷机的操作性优异,但印刷适合性尚有改善的余地。
现有技术文献
专利文献
专利文献1:日本特开2013-091715号公报
发明内容
发明要解决的问题
本发明的目的在于,提供:能构成印刷适合性良好的组合物的光固化性树脂组合物。
用于解决问题的方案
本发明人深入研究,结果发现:含有将具有特定结构的烯丙基系化合物聚合而得到的烯丙基系聚合物(A)和胶凝剂(B)的光固化性树脂组合物可以构成印刷适合性(流动性、印刷响应性)良好的组合物,想到了本发明。
即,本发明的光固化性树脂组合物的特征在于,含有:
将下述通式(I)所示的烯丙基系化合物聚合而得到的烯丙基系聚合物(A);和,胶凝剂(B)。
[R1和R2分别表示H或CH3,
X表示不具有取代基的饱和或一部分不饱和的四元~八元环的环状骨架、且为a价的基团,a表示2或3。]
含有将上述通式(I)所示的烯丙基系化合物聚合而得到的烯丙基系聚合物(A)和胶凝剂(B)时,成为印刷适合性优异的光固化性树脂组合物。
本发明的光固化性树脂组合物中,优选前述通式(I)中的X具有下述的任意环状骨架。
本发明的光固化性树脂组合物优选还含有烯属不饱和化合物(C)。
通过含有烯属不饱和化合物(C),光固化性树脂组合物的干燥性、所得固化物的覆膜强度提高,另外,可以调整为适合用于印刷的粘度,可以得到涂布作业性优异的组合物。
本发明的光固化性树脂组合物优选还含有光聚合引发剂。通过含有光聚合引发剂,由于利用光照射的聚合顺利进行,因此可以在短时间内得到更高分子量的聚合物。
本发明的油墨的特征在于,包含本发明的光固化性树脂组合物。
该油墨的印刷适合性优异。
本发明的涂料的特征在于,包含本发明的光固化性树脂组合物。
另外,本发明的涂料优选为罩印清漆。
发明的效果
根据本发明,可以得到在用作油墨、涂料、粘接剂和光致抗蚀剂的成分时印刷适合性(流动性、印刷响应性)优异的光固化性树脂组合物。
具体实施方式
本发明的光固化性树脂组合物含有将具有特定结构的烯丙基系化合物聚合而得到的烯丙基系聚合物(A)和胶凝剂(B),因此,可以降低低频区域(0.01~0.1Hz附近)中的储能模量,具有良好的流动性,和/或可以增大高频区域(10~100Hz附近)中的储能模量,提高高速印刷中的响应速度,可以得到良好的印刷响应性。
如此,本发明中,通过将烯丙基系聚合物(A)和胶凝剂(B)组合使用,可以得到良好的流动性和/或印刷响应性,印刷适合性优异,可以适合作为油墨、涂料使用。
另外,一般而言,流动性与印刷响应性是对立性能,但通过将烯丙基系聚合物(A)和胶凝剂(B)组合使用、进而使用铝络合物化合物作为胶凝剂(B),从而可以兼顾流动性和印刷响应性,印刷适合性更优异,可以更适合作为油墨、涂料使用。
需要说明的是,通过将烯丙基系聚合物(A)和胶凝剂(B)组合使用,可以降低低频区域(0.01~0.1Hz附近)中的储能模量是令人惊奇的发现。
推测:通过与烯丙基系聚合物(A)一起含有胶凝剂(B),模拟地形成交联链,高频区域中的储能模量增大,响应速度变快,可以得到良好的印刷响应性。另一方面,可以降低低频区域中的储能模量的理由尚不清楚,但推测:其源自烯丙基系聚合物(A)的环状骨架X的结构。
另外,印刷(特别是胶版印刷)时使用水(例如湿水)的情况下油墨中会混入水,但本发明的光固化性树脂组合物在不存在水的情况、存在水的情况的任意状态下,均可以降低低频区域中的储能模量,具有良好的流动性,和/或可以增大高频区域中的储能模量,提高高速印刷中的响应速度,可以得到良好的印刷响应性。
进而,已知作为胶版油墨使用时如果配混苯二甲酸二烯丙酯树脂,则与塑料基材的密合性不充分。近年来,市场上可购买到各种类的塑料制品,例如聚对苯二甲酸乙二醇酯(PET)、聚丙烯(PP)等,并且要求提高苯二甲酸二烯丙酯树脂与塑料基材的密合性,这正是它的缺点。
另一方面,本发明的光固化性树脂组合物的对塑料基材的密合性优异、特别是对PP(聚丙烯)树脂的密合性优异。另外,如果含有烯丙基系聚合物(A)和胶凝剂(B),则与其他树脂成分组合时可以构成相容性良好的组合物。因此,本发明的光固化性树脂组合物适合作为以往的使用苯二甲酸二烯丙酯树脂的组合物中难以提高密合性的PP树脂用的油墨、涂料的成分。
由此,本发明的油墨适合作为用于印刷至塑料基材的油墨,特别适合作为用于印刷至PP树脂制的片、薄膜等基材的油墨。
另外,本发明的涂料适合作为用于绘制至塑料基材的涂料,特别适合作为用于绘制至PP树脂制的片、薄膜等基材的涂料。
以下,对本发明详细进行说明。
烯丙基系聚合物(A)
本发明的光固化性树脂组合物含有将下述通式(I)所示的烯丙基系化合物聚合而得到的烯丙基系聚合物(A)。
[R1和R2分别表示H或CH3,
X表示不具有取代基的饱和或一部分不饱和的四元~八元环的环状骨架、且为a价的基团,a表示2或3。]
作为上述通式(I)中的X的优选例,可以举出以下的环状骨架。
作为上述通式(I)中的X的更优选例,可以举出以下的环状骨架。
作为上述通式(I)中的X的进一步优选例,可以举出以下的环状骨架。
X可以为各种骨架,也可以为除了上述之外的环状骨架。环状骨架为一部分不饱和的情况下,环状骨架所具有的双键的数量不限定于1,也可以为2以上。其中,X不是芳香族的六元环骨架。
X可以在分子内交联,作为在分子内交联的X的例子,可以举出:金刚烷、降冰片烯、降冰片烷等。
X为a价的基团,a为2或3,因此,X为2价或3价基团。X的环状骨架上键合有a个(2个或3个)的通式(I)中所示的烯丙酯基[-CO-O-CH2-CR2=CHR1]。
X的环上的烯丙酯基[-CO-O-CH2-CR2=CHR1]的取代位置可以为任意组合,也可以为烯丙基系化合物具有不同取代位置的组合的物质的混合物。特别是,2个烯丙酯基与六元环的X键合时,2个烯丙酯基为邻取向、间取向或对取向均可,优选为邻取向或对取向。
作为上述通式(I)所示的烯丙基系化合物的具体例,可以举出:1,2-环己烷二羧酸二烯丙酯、1,3-环己烷二羧酸二烯丙酯、1,4-环己烷二羧酸二烯丙酯、4-环己烯-1,2-二羧酸二烯丙酯、2-环己烯-1,2-二羧酸二烯丙酯等。其中,优选1,2-环己烷二羧酸二烯丙酯、4-环己烯-1,2-二羧酸二烯丙酯、1,4-环己烷二羧酸二烯丙酯,更优选1,2-环己烷二羧酸二烯丙酯。可以将选自由上述烯丙基系化合物组成的组中的至少1种以上聚合而得到的烯丙基系聚合物(A)用于光固化性树脂组合物。进而,也可以将上述通式(I)所示的烯丙基系化合物与其他能够聚合的化合物共聚而成的物质用于光固化性树脂组合物。作为能够共聚的化合物,例如可以举出苯二甲酸3-甲基-六氢-1,2-二烯丙酯、苯二甲酸4-甲基-六氢-1,2-二烯丙酯、苯二甲酸3-甲基-1,2,3,6-四氢-1,2-二烯丙酯、苯二甲酸4-甲基-1,2,3,6-四氢-1,2-二烯丙酯等。
作为得到以上述通式(I)所示的烯丙基系化合物的具体例而列举的化合物的方法的例子,可以举出:使环己烷二羧酸或环己烷二羧酸酐与烯丙醇或烯丙基酰氯进行酯化反应的方法;和,使环己烯二羧酸或环己烯二羧酸酐与烯丙醇或烯丙基酰氯进行酯化反应的方法。
另外,也可以使用以上述通式(I)所示的烯丙基系化合物的具体例而列举的化合物的市售品。
上述通式(I)所示的烯丙基系化合物的聚合方法没有特别限定,可以使用通常的聚合反应。根据需要,可以在上述聚合反应中适当添加聚合引发剂。通过使用聚合引发剂,可以在短时间内得到更高分子量的聚合物。
作为烯丙基系化合物的聚合反应中使用的聚合引发剂,可以举出:偶氮二异丁腈、2,2’-偶氮二异丁酸二甲酯等偶氮引发剂、酮过氧化物、过氧化缩酮、氢过氧化物、二烷基过氧化物、二酰基过氧化物、过氧化二碳酸酯、过氧化酯、过氧化苯甲酰等过氧化物引发剂、2-甲基-1-[4-(甲基硫代)苯基]-2-吗啉基-1-丙酮、1-羟基环己基苯基酮等苯乙酮系、苯偶姻、苯偶姻乙醚等苯偶姻系、二苯甲酮等二苯甲酮系、酰基氧化膦等磷系、噻吨酮等硫系、苯偶酰、9,10-菲醌等苯偶酰系的光聚合引发剂。
聚合引发剂的量相对于通式(I)所示的烯丙基系化合物的单体100重量份优选为5.0重量份以下、更优选为3.0重量份以下。另外,进一步优选为0.001~3.0重量份。
聚合时的反应温度优选为60~240℃、例如为80~220℃。反应时间优选为0.1~100小时、例如1~30小时。
利用上述方法等将上述通式(I)所示的烯丙基系化合物聚合,从而可以制备具有基于上述通式(I)所示的烯丙基系化合物的单体单元的烯丙基系聚合物(A)。
基于上述通式(I)所示的烯丙基系化合物的单体单元的含量在烯丙基系聚合物(A)100重量%中优选为20重量%以上、更优选为50重量%以上、进一步优选为80重量%以上、特别优选为98重量%以上,也可以为100重量%。
烯丙基系聚合物(A)的重均分子量优选为300000以下、更优选为200000以下。另外,进一步优选为2000~150000、特别优选为5000~140000。
本发明的光固化性树脂组合物中的烯丙基系聚合物(A)的含量相对于光固化性树脂组合物总量,优选1~60重量%、更优选2~55重量%、进一步优选5~50重量%。如果为上述范围内,则即使添加后述的胶凝剂(B)、烯属不饱和化合物(C),也保持充分溶解的状态,可以形成相容性优异的组合物,可以更适合地得到本发明的效果。
胶凝剂(B)
本发明中,作为含有烯丙基系聚合物(A)的光固化性树脂组合物中使用的胶凝剂(B),只要通过与烯丙基系聚合物(A)一起使用而可以形成模拟地交联链就没有特别限定。作为胶凝剂(B),例如可以举出铝络合物化合物,可以举出:环状铝化合物类、例如环状氧化辛酸铝(Kawaken Fine Chemical Company制Algomer 800)、环状氧化硬脂酸铝(KawakenFine Chemical Company制Algomer 1000S)等、作为铝醇盐类的乙醇铝、异丙醇铝(KawakenFine Chemical Company制AIPD)、仲丁醇铝(Kawaken Fine Chemical Company制ASPD)、二异丙醇单仲丁醇铝(Kawaken Fine Chemical Company制AMD)、铝烷基乙酸酯类、例如二正丁醇铝-乙酰乙酸乙酯(Hope Medicine Company制Chelope-Al-EB2)、二异丁醇铝-乙酰乙酸甲酯(Hope Medicine Company制Chelope-Al-MB12)、二异丁醇铝-乙酰乙酸乙酯(HopeMedicine Company制Chelope-Al-EB102)、二异丁醇铝-乙酰乙酸乙酯(Hope MedicineCompany制Chelope-Al-EB2)、二异丙醇铝-乙酰乙酸乙酯(Hope Medicine Company制Chelope-Al-EP12、Kawaken Fine Chemical Company制ALCH)、三(乙酰丙酮)铝(KawakenFine Chemical Company制ALCH-TR)、三(乙酰丙酮)铝(Kawaken Fine Chemical Company制铝螯合-A)、双(乙基乙酰丙酮)-单乙酰丙酮铝(Kawaken Fine Chemical Company制铝螯合D)、铝螯合M(Kawaken Fine Chemical Company制)、铝螯合NB-15(Hope MedicineCompany制)、Kelope S(Hope Medicine Company制)、Kelope ACS-2(Hope MedicineCompany制、液态Olive AOO(Hope Medicine Company制)、液态Olive AOS(Hope MedicineCompany制)。作为铝皂,可以举出硬脂酸铝(日油株式会社制)、油酸铝、萘酸铝、月桂酸铝、乙酰丙酮铝等。
作为其他胶凝剂(B),可以举出环状二肽类、具有使有机液体凝胶化的性质的亚乙基双(12-羟基十八烷酸)酰胺等双酰胺类、Al-Mg-羟基癸酸酯、Al-Mg-羟基肉豆蔻酸酯、Al-Mg-羟基棕榈酸酯、Al-Mg-羟基山萮酸酯等粉末状的铝-镁化合物。进而,可以举出AIP、ASB、AIE-M、ASE-M、OAO、OAO-EF、OAO-HT、Cyco-Gel、Ketalin、Ketalin-II、Ketalin-III、TRI-HLP-49、P-95、KHD、ATC-30、OASMS、OAS/607、ALAC、AO-L47(以上Chattem Chemicals,Inc)等。进而,可以举出钛酸四异丙酯、钛酸四正丁酯、四丁氧基钛、乙酰丙酮钛、钛辛二醇酯、钛乳酸酯、钛乳酸酯乙酯等有机钛酸酯等。另外,可以举出四丁醇锆、四丙醇锆、乙酰丙酮丁醇锆、乙酰乙酸乙酯丁醇锆等锆醇盐类、四乙酰丙酮锆、三丁氧基单乙酰丙酮锆、二丁氧基二乙酰丙酮锆、单丁氧基三乙酰丙酮锆、乙基乙酰乙酸酯锆、氯化锆化合物、乳酸锆铵盐等锆络合物化合物等有机锆等。
胶凝剂(B)中,优选铝络合物化合物、有机锆,优选铝烷基乙酸酯类、有机锆,更优选二异丙醇铝-乙酰乙酸乙酯、三(乙酰丙酮)铝、四丁醇锆、四乙酰丙酮锆、乙酰丙酮丁醇锆。
光固化性树脂组合物中含有的胶凝剂(B)的含量相对于光固化性树脂组合物的烯丙基系聚合物(A)100重量份,优选0.1~10重量份、更优选0.5~5重量份、特别优选1~3重量份。如果为上述范围内,则可以更适合地得到本发明的效果。另外,可以得到与塑料基材的充分的密合性,且保持烯丙基系聚合物(A)与胶凝剂(B)充分溶解的状态,成为相容性优异的组合物。进而,即使添加烯属不饱和化合物(C),也可以保持充分溶解的状态。
烯属不饱和化合物(C)
本发明的光固化性树脂组合物优选含有利用光照射能够固化的烯属不饱和化合物(C)。烯属不饱和化合物(C)优选具有1~20个碳-碳双键,更优选具有1~10个,进一步优选具有2~6个。作为烯属不饱和化合物(C),可以举出:(甲基)丙烯酸酯化合物、(甲基)烯丙基化合物和乙烯基化合物等。另外,烯属不饱和化合物也可以使用2种以上化合物的混合物。
作为(甲基)丙烯酸酯化合物,可以举出:季戊四醇、二季戊四醇、三羟甲基丙烷、二(三羟甲基)丙烷、新戊二醇、1,6-己二醇、丙三醇、聚乙二醇、聚丙二醇等醇类的(甲基)丙烯酸酯化合物、和在它们上加成环氧乙烷、环氧丙烷等环氧烷而得到的(甲基)丙烯酸酯化合物;在双酚A、双酚F等双酚类上加成环氧乙烷、环氧丙烷等环氧烷而得到的(甲基)丙烯酸酯化合物;环氧(甲基)丙烯酸酯、氨基甲酸酯(甲基)丙烯酸酯、醇酸(甲基)丙烯酸酯等(甲基)丙烯酸酯化合物;环氧化大豆油丙烯酸酯等(甲基)丙烯酸酯化合物,优选为季戊四醇、二季戊四醇、三羟甲基丙烷、二(三羟甲基)丙烷、新戊二醇、1,6-己二醇、丙三醇、聚乙二醇、聚丙二醇等醇类的(甲基)丙烯酸酯化合物、和在它们上加成环氧乙烷、环氧丙烷等环氧烷而得到的(甲基)丙烯酸酯化合物,更优选为季戊四醇、二季戊四醇、三羟甲基丙烷、二(三羟甲基)丙烷等醇类的(甲基)丙烯酸酯化合物、和在它们上加成环氧乙烷、环氧丙烷等环氧烷而得到的(甲基)丙烯酸酯化合物。
作为(甲基)烯丙基化合物,可以举出:苯二甲酸二(甲基)烯丙酯、异氰脲酸三(甲基)烯丙酯等。
作为乙烯基化合物,可以举出:苯乙烯、二乙烯基苯、N-乙烯基吡咯烷酮、乙酸乙烯酯等。
其中,从与烯丙基系聚合物(A)的相容性、光固化时的固化性的方面出发,优选二(三羟甲基)丙烷四丙烯酸酯、三羟甲基丙烷三丙烯酸酯、二季戊四醇六丙烯酸酯,更优选二(三羟甲基)丙烷四丙烯酸酯。
本发明的光固化性树脂组合物中含有的烯属不饱和化合物(C)的含量相对于光固化性树脂组合物中的烯丙基系聚合物(A)100重量份,优选50~1000重量份、更优选50~400重量份、进一步优选50~300重量份。
另外,光固化性树脂组合物中含有的烯属不饱和化合物(C)的含量优选以光固化性树脂组合物的粘度成为100~500Pa·s(25℃)的范围内的方式添加。
其他添加物
本发明的光固化性树脂组合物也可以包含聚合引发剂,特别优选含有光聚合引发剂。作为光固化性树脂组合物中含有的光聚合引发剂,可以举出:2-甲基-1-[4-(甲基硫代)苯基]-2-吗啉基-1-丙酮、1-羟基环己基苯基酮等苯乙酮系、苯偶姻、苯偶姻乙醚等苯偶姻系、二苯甲酮等二苯甲酮系、酰基氧化膦等磷系、噻吨酮等硫系、苯偶酰、9,10-菲醌等二苯偶酰系。
光固化性树脂组合物中含有的光聚合引发剂的量相对于光固化性树脂组合物整体优选为0.1~15重量%的范围、更优选为0.5~12重量%的范围、进一步优选为1~10重量%的范围。
光固化性树脂组合物中可以组合使用光引发助剂(例如三乙醇胺等胺系光引发助剂)。
光引发助剂的量相对于光固化性树脂组合物整体优选为0.1~5重量%的范围、更优选为0.5~3重量%的范围。
本发明的光固化性树脂组合物可以根据目的而含有各种添加剂,可列举稳定剂(例如氢醌、甲氧基苯酚等阻聚剂)、颜料(例如菁蓝、双偶氮黄、胭脂红6b、色淀红C(LakeRed C)、炭黑、钛白)等着色剂、填充剂、粘度调节剂(例如蜡)等各种添加剂。光固化性树脂组合物中含有的稳定剂的量相对于光固化性树脂组合物整体优选为0.01~2重量%的范围、更优选为0.1~1重量%的范围。
着色剂的量相对于光固化性树脂组合物整体优选为1~50重量%的范围、更优选为1~45重量%的范围。
本发明的光固化性树脂组合物与未配混胶凝剂(B)的光固化性树脂组合物相比,通过配混胶凝剂(B),优选0.01Hz(低频区域)中的储能模量优选成为70%以下、更优选成为50%以下、进一步优选成为40%以下。由此,可以得到更良好的流动性。
另外,本发明的光固化性树脂组合物与未配混胶凝剂(B)的光固化性树脂组合物相比,通过配混胶凝剂(B),优选10Hz(高频区域)中的储能模量优选成为120%以上、更优选成为150%以上。由此,可以得到更良好的印刷响应性。
此处,储能模量是通过实施例中记载的方法测定的值。
本发明的光固化性树脂组合物可以通过在烯丙基系聚合物(A)中加入胶凝剂(B),根据需要混合烯属不饱和化合物(C)、进而光聚合引发剂、光引发助剂、添加剂(例如稳定剂、颜料)来制造。本发明的光固化性树脂组合物通过照射光而固化。固化中使用的光一般为紫外线。
光固化性树脂组合物的固化反应中使用的固化装置、以及固化条件没有特别限定,只要为通常的光固化反应中使用的方法即可。
本发明的光固化性树脂组合物的用途没有特别限定。可以在油墨(例如光固化性平版用印刷油墨、丝网印刷油墨、凹印油墨等印刷油墨)、涂料(例如纸用、塑料用、金属用、木工用等的涂料,可列举罩印清漆)、粘接剂、光致抗蚀剂等技术领域中使用。
包含本发明的光固化性树脂组合物的油墨是本发明的油墨,包含本发明的光固化性树脂组合物的涂料是本发明的涂料。另外,本发明的涂料优选为罩印清漆。
例如,油墨的一般的制作方法如下所述。在60℃~120℃的温度下,边搅拌边使烯丙基系聚合物(A)、胶凝剂(B)和稳定剂等溶解于烯属不饱和化合物(C)中,制作清漆。用Butterfly Mixer在该清漆中将颜料、光聚合引发剂、其他添加剂搅拌混合后,用三辊磨等进行研墨,从而得到油墨。
另外,罩印清漆的制成除了不使用颜料之外,可以通过与油墨同样的步骤进行。
(实施例)
以下,列举实施例对本发明进行更具体地说明,但本发明不限定于这些实施例。
烯丙基系聚合物的重均分子量(Mw)、分子量分布(Mw/Mn)的测定重均分子量(Mw)、分子量分布(Mw/Mn)使用GPC进行测定。是标准聚苯乙烯换算的重均分子量的值。
柱:将ShodexKF-806L、KF-804、KF-803、KF-802、KF-801串联连接
流速:1.0mL/分钟
温度:40℃
检测:RID-6A
试样:使试样20mg溶解于四氢呋喃10mL作为测定用的样品。
制造例1 1,2-环己烷二羧酸二烯丙酯聚合物的合成
1,2-环己烷二羧酸二烯丙酯通过使环己烷二羧酸酐和烯丙醇进行酯化反应来制造。
在3L的可拆式烧瓶中加入1,2-环己烷二羧酸二烯丙酯2400g,加入60g的过氧化苯甲酰,在80℃下进行加热搅拌。使其反应2.5小时后,冷却至30℃。冷却后,向烧瓶中加入甲醇,使聚合物沉淀。将所得聚合物在40℃下进行16小时减压干燥(收量:408g、收率:17%、Mw=32000、Mw/Mn=2.8)。将所得聚合物作为聚合物1。
(实施例1、2)
(1)清漆的制备
以树脂(上述聚合物1)35重量份、DTMPTA(SR-355NS:Sartomer公司制的二(三羟甲基)丙烷四丙烯酸酯)65重量份、阻聚剂(IRGANOX1076:BASF Japan株式会社制的3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷酯)0.3重量份的比率投入,在100℃下使其热溶解,制备微淡黄色透明的清漆。
(2)凝胶清漆的制备
相对于(1)中制备的清漆100重量份,添加胶凝剂(ALCH:Kawaken Fine ChemicalCompany制的二异丙醇铝-乙酰乙酸乙酯(铝络合物化合物))0.6重量份(实施例1)、胶凝剂(Orgatics ZC-150:Matsumoto Fine Chemical Co.,Ltd.制的四乙酰丙酮锆(有机锆))1.0重量份(实施例2),在110℃下搅拌1小时,制备透明的凝胶清漆。
(3)油墨的制备
光固化性油墨的制备方法
将上述(2)中制备的凝胶清漆62.6重量份、二(三羟甲基)丙烷四丙烯酸酯(DTMPTA)10.4重量份、聚乙烯蜡2重量份、光聚合引发剂(Irgacure907:BASF Japan株式会社制、2-甲基-1-[4-(甲基硫代)苯基]-2-吗啉基-1-丙酮5重量份、颜料(酞菁蓝)20重量份用三辊磨研磨,制备油墨。
(比较例1)
使用(1)中制备的清漆代替凝胶清漆(上述(2)中制备的凝胶清漆),除此之外,通过与实施例1、2同样的方法,制备油墨。
(动态粘弹性测定)
使用制备好的实施例1、2和比较例1的油墨,进行动态粘弹性测定,测定储能模量。需要说明的是,对于假定混入了水的情况的“乳化后的”试验,相对于油墨100重量份添加水100重量份后,用分散器搅拌混合3分钟,制备乳化后的油墨,使用乳化后的油墨进行粘弹性试验。
(动态粘弹性测定的条件)
用HAAKE MARS III粘弹性测定装置(Thermo Scientific公司制),使用直径35mm、锥角2度的锥板,在25℃下进行频率扫描测定。
测定好的储能模量是将比较例1的结果设为100进行指数表示,将评价结果示于表1。指数越大,表示储能模量越大。
(粘度测定)
对于制备好的凝胶清漆、清漆,使用BROOKFIELD VISCOMETER DV-II+Pro,测定25℃下的粘度(Pa·s)。将评价结果示于表1。
[表1]
由表1可知,对于含有将具有特定结构的烯丙基系化合物聚合而得到的烯丙基系聚合物(A)和胶凝剂(B)的实施例1,在不存在水的情况(乳化前)、存在水的情况(乳化后)的任意状态下,均可以降低低频区域中的储能模量,具有良好的流动性,且可以增大高频区域中的储能模量,提高高速印刷中的响应速度,可以得到良好的印刷响应性。另外,对于实施例2,在不存在水的情况(乳化前)、存在水的情况(乳化后)的任意状态下,均可以降低低频区域中的储能模量,具有良好的流动性。即,可知通过将烯丙基系聚合物(A)和胶凝剂(B)组合使用,可以得到良好的流动性和/或印刷响应性,印刷适合性优异,可以适合作为油墨使用。
另外,通过添加胶凝剂,清漆的粘度上升,可以增大高频区域中的储能模量,通过与烯丙基系聚合物(A)一起含有胶凝剂(B),模拟地形成交联链。进而,实施例1的凝胶清漆的外观为无色透明,实施例2的凝胶清漆的外观为淡黄色透明,可以适合用于油墨(例如胶版油墨)、涂料、粘接剂、光致抗蚀剂等。
产业上的可利用性
本发明的光固化性树脂组合物可以用于油墨(例如胶版油墨)、涂料、粘接剂、光致抗蚀剂等(特别是作为塑料基材用)。
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