CN109641985A - 光固化性树脂组合物、油墨及涂料 - Google Patents
光固化性树脂组合物、油墨及涂料 Download PDFInfo
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- CN109641985A CN109641985A CN201780051267.5A CN201780051267A CN109641985A CN 109641985 A CN109641985 A CN 109641985A CN 201780051267 A CN201780051267 A CN 201780051267A CN 109641985 A CN109641985 A CN 109641985A
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Abstract
本发明提供与塑料基材的密合性优异的包含聚合物(A)的光固化性树脂组合物。本发明涉及光固化性树脂组合物,其特征在于,含有使通式[I]所示的化合物聚合而得到的聚合物(A)(式中,R1表示[‑CH2‑CR3=CHR2]基、缩水甘油基、碳数1~5的烷基或氢原子,各个R1任选不同或相同,其中至少1个为[‑CH2‑CR3=CHR2]基,[‑CH2‑CR3=CHR2]基中的R2及R3各自表示H或CH3。)。
Description
技术领域
本发明涉及含有使通式[I]所示的化合物聚合而得到的聚合物(A)的光固化性树脂组合物、以及包含该树脂组合物的油墨、涂料。更详细而言,涉及与塑料基材的密合性优异的光固化性树脂组合物。
背景技术
以往,通过光(例如紫外线)固化的各种树脂组合物用于油墨、涂料、粘接剂、光致抗蚀剂等。例如,紫外线固化型的印刷油墨在如下方面被高度评价并展开了实用化:固化速度快、能够在短时间内固化;由于不使用溶剂而适于环境;节省资源/节能等。
这样的树脂组合物中,采用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胶印油墨。
但是,已知在作为胶印油墨使用时,若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(例如,专利文献1)。另外,记载了一种非吸收材料用紫外线固化型喷墨墨水组合物,其含有颜料、紫外线固化性树脂、光聚合引发剂,且紫外线固化性树脂中包含具有三嗪环的3官能以上的烯丙基、聚酯丙烯酸酯和(甲基)丙烯酸酯(专利文献2)。但是,为喷墨用的组合物,在对塑料基材的密合性、干燥性的方面不充分。
近年来,聚对苯二甲酸乙二醇酯(PET)、聚丙烯(PP)等各种塑料制品已经商品化,并且需要改善与塑料基材的密合性、即苯二甲酸二烯丙酯树脂的缺点。
现有技术文献
专利文献
专利文献1:日本特开昭52-4310号公报
专利文献2:日本特开2005-68255号公报
发明内容
发明要解决的问题
本发明的目的在于,提供与塑料基材的密合性优异的包含聚合物(A)的光固化性树脂组合物。
用于解决问题的方案
本发明人进行了深入研究,结果发现,含有使具有特定结构的化合物聚合而得到的聚合物(A)的光固化性树脂组合物与塑料基材的密合性优异,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,
含有使下述通式[I]所示的化合物聚合而得到的聚合物(A)。
(式中,R1表示[-CH2-CR3=CHR2]基、缩水甘油基、碳数1~5的烷基或氢原子,各个R1任选不同或相同,其中至少1个为[-CH2-CR3=CHR2]基,[-CH2-CR3=CHR2]基中的R2及R3各自表示H或CH3。)
含有使上述通式[I]所示的化合物聚合而得到的聚合物(A)时,会成为对塑料基材的密合性优异、干燥性也优异的光固化性树脂组合物。
另外,该光固化性树脂组合物特别是对PP(聚丙烯)树脂的密合性优异,因此,适合作为对于以往的使用苯二甲酸二烯丙酯树脂的组合物而言难以提高密合性的PP树脂用的油墨、涂料的成分。
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(B)。通过使用烯属不饱和化合物,从而光固化性树脂组合物的干燥性提高,能够调整为适合用于印刷的粘度,成为涂布操作性优异的组合物。
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,从而基于光照射的聚合顺利地进行,因此能够以短时间得到固化物。
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。
该油墨适合作为用于在塑料基材上印刷的油墨,特别适合作为用于在PP树脂制的片、薄膜等基材上印刷的油墨。
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。
该涂料适合作为用于在塑料基材上描绘的涂料,特别适合作为用于在PP树脂制的片、薄膜等基材上描绘的涂料。
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,作为油墨、涂料、粘接剂及光致抗蚀剂的成分使用的情况下,可得到对合成高分子的基材、特别是塑料基材的密合性优异的光固化性树脂组合物。
具体实施方式
以下,详细地对本发明进行说明。
聚合物(A)
本发明的光固化性树脂组合物的特征在于,含有使下述通式[I]所示的化合物聚合而得到的聚合物(A)。
本发明中,对于通过含有聚合物(A)从而对合成高分子的基材、特别是塑料基材的密合性优异的理由尚不确定,但推测如下。
推测为:在使下述通式[I]所示的化合物聚合而得到的聚合物(A)中,连续存在有基于异氰脲酸酯环的结构(下述通式[I]中的环结构(异氰酸酯的三聚体)),并且通过连续存在的基于异氰脲酸酯环的结构,对合成高分子的基材、特别是塑料基材的密合性优异。
(式中,R1表示[-CH2-CR3=CHR2]基、缩水甘油基、碳数1~5(优选碳数1~3)的烷基或氢原子,各个R1任选不同或相同,其中至少1个(特别优选2个、更优选3个)为[-CH2-CR3=CHR2]基,[-CH2-CR3=CHR2]基中的R2及R3各自表示H或CH3。)
如上所述,对于R1,至少1个为[-CH2-CR3=CHR2]基,优选2个为[-CH2-CR3=CHR2]基,更优选3个为[-CH2-CR3=CHR2]基。[-CH2-CR3=CHR2]基的数量越多,反应性越提高,变得容易得到更高分子量的聚合物。
对于R2及R3,优选为H(氢原子)、更优选均为H(氢原子)。
通式[I]中,R1为烷基的情况下,可列举出甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基等,其中,优选甲基、乙基、丙基、异丙基,更优选甲基、乙基。
作为具有通式[I]所示的结构的化合物的具体例,可列举出三烯丙基异氰脲酸酯、二烯丙基单缩水甘油基异氰脲酸酯、二烯丙基单甲基异氰脲酸酯、二烯丙基单乙基异氰脲酸酯、二烯丙基单丙基异氰脲酸酯、三甲代烯丙基异氰脲酸酯、二烯丙基异氰脲酸酯、单烯丙基二甲基异氰脲酸酯、单烯丙基二乙基异氰脲酸酯、单烯丙基二丙基异氰脲酸酯、单烯丙基二缩水甘油基异氰脲酸酯、单烯丙基单乙基单甲基异氰脲酸酯、单烯丙基异氰脲酸酯、单烯丙基二甲代烯丙基异氰脲酸酯、单烯丙基单甲代烯丙基单甲基异氰脲酸酯等。这些当中,优选三烯丙基异氰脲酸酯、二烯丙基单缩水甘油基异氰脲酸酯、二烯丙基单甲基异氰脲酸酯、二烯丙基异氰脲酸酯,更优选三烯丙基异氰脲酸酯、二烯丙基单甲基异氰脲酸酯、二烯丙基异氰脲酸酯,特别优选三烯丙基异氰脲酸酯。
可以将通过使上述式[I]所示的化合物聚合而得到的聚合物(A)用于光固化性树脂组合物。进而也可以将使上述通式[I]所示的化合物与其他可聚合的化合物共聚而得到的聚合物用于光固化性树脂组合物。作为可共聚的化合物,可列举出丙烯酸甲酯、丙烯酸丁酯等丙烯酸酯类、乙酸乙烯酯、月桂酸乙烯酯、苯甲酸乙烯酯等各种脂肪族及芳香族羧酸乙烯基酯类、氯乙烯、溴乙烯等乙烯基类、偏二氯乙烯、偏二溴乙烯等偏二烯类、甲基乙烯基醚、丁基乙烯基醚等乙烯基烷基醚类、三羟甲基丙烷二烯丙基醚、季戊四醇三烯丙基醚等烯丙基醚类、乙酸烯丙酯、苯甲酸烯丙酯等各种脂肪族及芳香族羧酸烯丙基酯类、对苯二甲酸二烯丙酯、柠檬酸三烯丙酯等多元酸烯丙基酯类等。聚合物(A)中的共聚成分的配混比率为2~50重量%即可,优选为2~20重量%。
对于作为获得上述通式[I]所示的化合物的具体例而举出的化合物的方法的例子,可以通过通常已知的聚合方法来合成,也可以使用市售品。
上述通式[I]所示的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,上述聚合反应中可以适宜添加聚合引发剂。通过使用聚合引发剂,从而能够在短时间内获得更高分子量的聚合物(A)。
作为通式[I]所示的化合物的聚合反应中使用的聚合引发剂,可列举出偶氮双异丁腈、2,2’-偶氮双异丁酸二甲酯等偶氮引发剂、酮过氧化物、过氧化缩酮、过氧化氢、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-吗啉基丙烷-1-酮、1-羟基环己基苯基酮等苯乙酮系、苯偶姻、苯偶姻乙基醚等苯偶姻系、二苯甲酮等二苯甲酮系、酰基氧化膦等磷系、噻吨酮等硫系、联苯酰、9,10-菲醌等苯偶酰系的光聚合引发剂。
对于聚合引发剂的量,相对于通式[I]所示的化合物的单体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,特别优选为0.001~3.0重量份。
聚合时的反应温度为60~240℃,例如优选为80~220℃。反应时间为0.1~100小时,例如优选为1~30小时。
通过上述方法等使上述通式[I]所示的化合物聚合,由此能够制备具有基于上述通式[I]所示的化合物的单体单元的聚合物(A)。
对于基于上述通式[I]所示的化合物的单体单元的含量,在聚合物(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,可以为100重量%。
聚合物(A)的重均分子量(Mw)优选为250000以下、更优选为200000以下。另外,聚合物(A)的重均分子量优选为2000以上、更优选为5000以上。另外,聚合物(A)的重均分子量进一步优选为10000~150000、特别优选为20000~140000。
聚合物(A)的分子量分布(重均分子量(Mw)/数均分子量(Mn))优选1.5~10.0、更优选3.0~7.5。
本说明书中,聚合物(A)的重均分子量(Mw)、数均分子量(Mn)为通过实施例中记载的方法测定的值。
对于本发明的光固化性树脂组合物中的聚合物(A)的含量,相对于光固化性树脂组合物总量,优选为1~50重量%、更优选为1~40重量%、进一步优选为1~30重量%。下限特别优选为1重量%,可以为5重量%。若聚合物(A)的含量超过50重量%,则有时在烯属不饱和化合物(B)中的溶解性变差、粘度也变高、处理性变差。若聚合物(A)的含量不足1重量%,则有时得到的光固化性树脂组合物得不到充分的干燥性、密合性。
烯属不饱和化合物(B)
本发明的光固化性树脂组合物优选含有通过光照射可固化的烯属不饱和化合物(B)。烯属不饱和化合物(B)优选具有碳-碳双键1~20个、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(B),可列举出(甲基)丙烯酸酯化合物、(甲基)烯丙基化合物及乙烯基化合物等。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,可例示出季戊四醇、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、甘油、聚乙二醇、聚丙二醇等醇类的(甲基)丙烯酸酯化合物、及在上述物质上加成环氧乙烷、环氧丙烷等环氧烷烃而得到的(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、环氧丙烷等环氧烷烃而得到的物质的(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、甘油、聚乙二醇、聚丙二醇等醇类的(甲基)丙烯酸酯化合物、及在上述物质上加成环氧乙烷、环氧丙烷等环氧烷烃而得到的(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、及在上述物质上加成环氧乙烷、环氧丙烷等环氧烷烃而得到的(甲基)丙烯酸酯化合物。
作为(甲基)烯丙基化合物,可例示出二(甲基)烯丙基苯二甲酸酯等。
作为乙烯基化合物,可例示出苯乙烯、二乙烯基苯、N-乙烯基吡咯烷酮、乙酸乙烯酯等。
其中,从与聚合物(A)的相容性、进行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、及在上述物质上加成环氧乙烷、环氧丙烷等环氧烷烃而得到的物质。
对于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(B)的含量,相对于光固化性树脂组合物中的聚合物(A)100重量份,优选为50~1200重量份、更优选为50~1000重量份、进一步优选为100~900重量份。
另外,本发明的光固化性树脂组合物中的聚合物(A)与烯属不饱和化合物(B)的比率(聚合物:烯属不饱和化合物)以重量比计为5:95~95:5的范围即可,优选为10:90~90:10的范围、更优选为10:90~70:30的范围、进一步优选为10:90~50:50的范围。为上述范围内时,容易得到对塑料基材的充分的密合性。
其他添加物
本发明的光固化性树脂组合物可以含有聚合引发剂,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,可列举出2-甲基-1-[4-(甲基硫代)苯基]-2-吗啉基丙烷-1-酮、1-羟基环己基苯基酮等苯乙酮系、苯偶姻、苯偶姻乙基醚等苯偶姻系、二苯甲酮等二苯甲酮系、酰基氧化膦等磷系、噻吨酮等硫系、联苯酰、9,10-菲醌等苯偶酰系。
对于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0.5~12重量%的范围、进一步优选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含有各种添加剂,可例示出稳定剂(例如,氢醌、对羟基苯甲醚、甲基氢醌等阻聚剂)、颜料(例如,酞菁蓝、双偶氮黄(disazoyellow)、宝红6b(carmine 6b)、色淀红C(lake red C)、炭黑、钛白)等着色剂、填充剂、粘度调整剂等。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1~45重量%的范围。
本发明的光固化性树脂组合物可以通过在聚合物(A)中根据需要混合烯属不饱和化合物(B)、以及光聚合引发剂、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发生固化。固化中使用的光通常为紫外线。
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,为通常的光固化反应中所用的方法即可。
本发明的光固化性树脂组合物的用途没有特别限定。可以用于油墨(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、木工用等涂料、可例示出罩印清漆)、粘接剂、光致抗蚀剂等的技术领域。
包含本发明的光固化性树脂组合物的油墨为本发明的油墨,包含本发明的光固化性树脂组合物的涂料为本发明的涂料。另外,本发明的涂料优选为罩印清漆。
例如,油墨的通常的制作方法如下。边将聚合物(A)及稳定剂等在60℃~100℃的温度下搅拌边使之溶解于烯属不饱和化合物(B),制作清漆。在该清漆中将颜料、光聚合引发剂、其他添加剂用蝶形搅拌机搅拌混合后,用三辊磨等进行研墨,由此得到油墨。
另外,对于罩印清漆的制作,除了不使用颜料以外,通过与油墨同样的步骤进行。
(实施例)
以下,举出实施例,更具体地对本发明进行说明,但本发明并不限定于这些实施例。
聚合物(A)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。Mw、Mn为标准聚苯乙烯换算的重均分子量、数均分子量的值。
柱:将ShodexLF-804×2根串联连接
流速:1.0mL/分钟
温度:40℃
检测:RID-20A
试样:使试样30mg溶解于四氢呋喃3mL,作为测定用的样品。
制造例1三烯丙基异氰脲酸酯聚合物1的合成
在3L的可拆式烧瓶中加入三烯丙基异氰脲酸酯600g,加入15g过氧化苯甲酰,在80℃下加热搅拌。反应1小时后,冷却至室温(25℃)。冷却后,向烧瓶中加入甲醇,使聚合物沉淀。将得到的聚合物在40℃下进行16小时减压干燥(收量:73g、收率:12%、Mw=53000、Mw/Mn=3.3)。将得到的聚合物作为聚合物1,用于实施例1、4~6。
制造例2三烯丙基异氰脲酸酯聚合物2的合成
将制造例1的反应时间设为1.25小时,除此以外,通过同样的方法进行合成。(收量:84g、收率:14%、Mw=94000、Mw/Mn=5.3)。将得到的聚合物作为聚合物2,用于实施例2。
制造例3三烯丙基异氰脲酸酯聚合物3的合成
将制造例1的反应时间设为1.5小时,除此以外,通过同样的方法进行合成。(收量:94g、收率:16%、Mw=126000、Mw/Mn=6.9)。将得到的聚合物作为聚合物3,用于实施例3。
实施例1~6、比较例1、2
制备下述表1中记载的各组成的光固化性树脂组合物,对光固化性树脂组合物的特性进行评价。
[表1]
表1所示的聚合物1~3以外的成分如下。
另外,表1所示的组成量用重量份来表示。
DAP树脂:OSAKASODACO.,LTD.制DAISO DAP A(苯二甲酸二烯丙酯树脂)
三烯丙基异氰脲酸酯(单体)
DTMPTA:Sartomer株式会社制SR355二(三羟甲基)丙烷四丙烯酸酯
Irgacure907:BASF JAPAN LTD.制2-甲基-1-[4-(甲基硫代)苯基]-2-吗啉基丙烷-1-酮
Irganox1076:BASF JAPAN LTD.制十八烷基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯
1)光固化性树脂组合物的溶解性的评价
按表1中记载的各组成量添加各制造例中得到的各聚合物1~3、DAP树脂、三烯丙基异氰脲酸酯(单体)、烯属化合物、及聚合引发剂,进行加热混合,制备光固化性树脂组合物。将各组合物冷却至室温(25℃)后,通过经过一晚后的外观是否为透明来确认溶解性。将冷却后外观仍透明的组合物记为○、将发生了白浊的组合物记为×。将结果示于表2。
2)干燥性试验
用RI测试仪将制备的光固化性树脂组合物涂布于塑料薄膜(聚丙烯基材:龙田化学株式会社制无拉伸高透明PP片商品名:High P Crystal ST-500厚度0.3mm),用输出120W/cm的金属卤化物灯(灯距离11cm、传送带速度50m/分钟)使其固化。需要说明的是,UV固化装置使用EYE GRAPHICS CO.,LTD.制传送带型紫外线固化装置。用手指触摸涂膜,使其通过多次直至达到表面没有指纹的状态(不粘手)为止,用该次数来评价干燥性。将评价结果示于表2。
3)密合性试验
通过与干燥性试验同样的方法将制备的光固化性树脂组合物涂布于塑料薄膜并使其固化。在得到的涂膜上贴附Nichiban Co.,Ltd.制的宽18mm的Cellotape(注册商标、产品编号:LP-18、粘合力:4.01N/10mm),用拇指强烈摩擦10次后,在正上方将Cellotape(注册商标)缓慢剥离。将完全没发生剥离者记为○、将完全剥离者记为×。将评价结果示于表2。
[表2]
实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 比较例1 | 比较例2 | |
溶解性 | ○ | ○ | ○ | ○ | ○ | ○ | ○ | ○ |
干燥性(次) | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 3 |
密合性(PP片) | ○ | ○ | ○ | ○ | ○ | ○ | × | × |
由实施例1~6所示,使用使通式[I]所示的化合物聚合而得到的聚合物1~3制备的光固化性树脂组合物与比较例1所示的使用DAP树脂制备的光固化性树脂组合物具有同等干燥性。而且,对于对使用DAP树脂制备的比较例1、使用三烯丙基异氰脲酸酯(单体)进行了调整的比较例2的光固化性树脂组合物而言难以密合的聚丙烯片的密合性也优异。
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塑料基材用的油墨(例如,胶印油墨)、涂料、粘接剂、光致抗蚀剂等。
Claims (6)
1.一种光固化性树脂组合物,其含有使通式[I]所示的化合物聚合而得到的聚合物(A),
式中,R1表示[-CH2-CR3=CHR2]基、缩水甘油基、碳数1~5的烷基或氢原子,各个R1任选不同或相同,其中至少1个为[-CH2-CR3=CHR2]基,[-CH2-CR3=CHR2]基中的R2及R3各自表示H或CH3。
2.根据权利要求1所述的光固化性树脂组合物,其特征在于,还含有烯属不饱和化合物(B)。
3.根据权利要求1或2所述的光固化性树脂组合物,其中,还含有光聚合引发剂。
4.一种油墨,其特征在于,包含权利要求1~3中任一项所述的光固化性树脂组合物。
5.一种涂料,其特征在于,包含权利要求1~3中任一项所述的光固化性树脂组合物。
6.根据权利要求5所述的涂料,其为罩印清漆。
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- 2017-08-08 CN CN201780051267.5A patent/CN109641985B/zh active Active
- 2017-08-08 US US16/323,697 patent/US11149157B2/en active Active
- 2017-08-08 WO PCT/JP2017/028766 patent/WO2018037912A1/ja active Application Filing
- 2017-08-08 KR KR1020197003656A patent/KR20190043530A/ko not_active IP Right Cessation
- 2017-08-08 JP JP2018535588A patent/JP7081486B2/ja active Active
- 2017-08-08 EP EP17843397.5A patent/EP3502150A4/en active Pending
- 2017-08-10 TW TW106127016A patent/TWI808944B/zh active
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Also Published As
Publication number | Publication date |
---|---|
US11149157B2 (en) | 2021-10-19 |
CN109641985B (zh) | 2022-04-22 |
EP3502150A1 (en) | 2019-06-26 |
WO2018037912A1 (ja) | 2018-03-01 |
KR20190043530A (ko) | 2019-04-26 |
JPWO2018037912A1 (ja) | 2019-06-20 |
US20190203061A1 (en) | 2019-07-04 |
JP7081486B2 (ja) | 2022-06-07 |
EP3502150A4 (en) | 2020-01-22 |
TW201809171A (zh) | 2018-03-16 |
TWI808944B (zh) | 2023-07-21 |
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