CN108138021A - 聚氨基甲酸酯粘合剂组合物 - Google Patents
聚氨基甲酸酯粘合剂组合物 Download PDFInfo
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Abstract
本发明提供一种粘合剂组合物,按所述粘合剂组合物的总干重计,其包含70干重%到96干重%聚氨基甲酸酯分散体、1干重%到20干重%环氧树脂和0.5干重%到15干重%脂族胺交联剂。本发明进一步提供一种包含所述粘合剂组合物的层压材料。
Description
技术领域
本发明涉及一种粘合剂组合物和其用于制造层压材料的方法。本发明尤其涉及一种具有良好的粘接强度、热封强度和连袋煮沸抗性(boil in bag resistance)的聚氨基甲酸酯粘合剂组合物。所述聚氨基甲酸酯粘合剂组合物特别适合于粘接聚乙烯和金属。
前言
总的来说,粘合剂组合物的功能是将选自聚乙烯(PE)、聚丙烯、聚酯、聚酰胺、金属、纸或玻璃纸的衬底粘接在一起以形成复合膜,即用于不同目的的层压材料。不同的衬底和应用目的对涂覆于其上的粘合剂具有不同的偏好和要求。为了将聚乙烯衬底与金属衬底粘接,例如,要求粘合剂在粘接强度(BS)、热封强度(HS)和连袋煮沸抗性(BBR)方面表现特别好。
由其制成的层压材料通常用于包装工业,特别用于制造食品包装。由于环境、健康和安全原因,粘合剂优选是水性的或不含溶剂的。
因此,期望提供在BS、HS和BBR方面具有良好性能的聚氨基甲酸酯粘合剂组合物,因此其特别适合于粘接PE和金属。
发明内容
本发明提供一种粘合剂组合物,按所述粘合剂组合物的总干重计,其包含70干重%到96干重%聚氨基甲酸酯分散体、1干重%到20干重%环氧树脂和0.5干重%到15干重%脂族胺交联剂。
本发明进一步提供包含粘合剂组合物的层压材料。
具体实施方式
按粘合剂组合物的总干重计,本发明的粘合剂组合物包含70干重%到96干重%、优选75干重%到93干重%且更优选80干重%到90干重%聚氨基甲酸酯分散体、1干重%到20干重%、优选2干重%到15干重%且更优选3干重%到13干重%的环氧树脂和0.5干重%到15干重%、优选0.7干重%到12干重%且更优选为1.0干重%到10干重%脂族胺交联剂。
粘合剂组合物是水性的,并且优选不含溶剂的,也就是说,按粘合剂组合物的总干重计,粘合剂组合物包含小于4干重%、优选小于2干重%且更优选小于1干重%有机溶剂。
有机溶剂是在25℃下呈液体并且沸点低于300℃的化合物。
聚氨基甲酸酯分散体
聚氨基甲酸酯分散体是通过在离子型表面活性剂的协助下将聚氨基甲酸酯预聚物分散到水中来制备的。
按聚氨基甲酸酯预聚物的总干重计,聚氨基甲酸酯预聚物包含:10干重%到40干重%、优选12干重%到38干重%且更优选15干重%到35干重%单体芳香族二异氰酸酯和20干重%到85干重%、优选25干重%到80干重%且更优选30干重%到75干重%聚醚多元醇作为聚合单元。
任选地,按聚氨基甲酸酯预聚物的总干重计,聚氨基甲酸酯预聚物进一步包含0.1干重%到30干重%、优选18干重%到28干重%且更优选20干重%到25干重%聚酯多元醇作为聚合单元。
单体芳香族二异氰酸酯的分子量Mw优选小于500g/mol、优选小于300g/mol且更优选小于275g/mol。
优选单体芳香族二异氰酸酯选自二苯基甲烷二异氰酸酯(MDI)、甲苯二异氰酸酯(TDI)和其组合。TDI通常可以带有任何常用的异构体分布一起使用。最常用的TDI的异构体分布是80%2,4-异构体和20%2,6-异构体。也可以使用具有其他异构体分布的TDI。当使用MDI制备聚氨基甲酸酯预聚物时,其优选是纯4,4'-MDI或MDI异构体的任意组合。更优选地,其是纯4,4'-MDI和4,4'-MDI与其他MDI异构体的任意组合。当使用4,4'-MDI与其他MDI异构体的组合时,4,4'-MDI的优选浓度是所有MDI异构体的25%到75%。
聚醚多元醇和聚酯多元醇的分子量Mw各个都是400到4000g/mol、优选750到3500g/mol且更优选800到3000g/mol。聚醚多元醇和聚酯多元醇的官能度各个都是1.8到4、优选1.9到3且更优选2到2.5。
聚醚多元醇是环氧乙烷、环氧丙烷、四氢呋喃与环氧丁烷的加聚产物和接枝产物、多元醇的缩合产物和其任意组合。聚醚多元醇的合适实例包括聚丙二醇(PPG)、聚乙二醇(PEG)、聚丁二醇、聚四亚甲基醚二醇(PTMEG)和其任意组合。聚醚多元醇优选是PEG与至少一种选自上述加聚和接枝产物以及缩合产物的另一种聚醚多元醇的组合。聚醚多元醇更优选是PEG与PPG、聚丁二醇和PTMEG中的至少一种的组合。
聚酯多元醇是二醇的缩合产物或其衍生物以及二羧酸和其衍生物。
二醇的合适实例是乙二醇、丁二醇、二乙二醇、三乙二醇、聚亚烷基二醇(诸如聚乙二醇、1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、1,6-己二醇、新戊二醇、3-甲基-1,5-戊二醇和其任意组合)。为了实现大于2的多元醇官能度,也可以使用三醇和/或四醇。这种三醇的合适实例包括三羟甲基丙烷和丙三醇。这种四醇的合适实例包括赤藓醇和季戊四醇。
二羧酸选自芳香族酸、脂族酸和其组合。芳香族酸的合适实例是邻苯二甲酸、间苯二甲酸和对苯二甲酸;而脂肪酸的合适实例是己二酸、壬二酸、癸二酸、戊二酸、四氯邻苯二甲酸、马来酸、富马酸、衣康酸、丙二酸、辛二酸、2-甲基琥珀酸、3,3-二乙基戊二酸和2,2-二甲基琥珀酸。这些酸的酸酐同样也可以使用。为了本发明的目的,酸酐因此涵盖在术语“酸”的表述中。优选地,所述脂族酸和芳香族酸是饱和的,并且分别是己二酸和间苯二甲酸。诸如苯甲酸和己烷羧酸的一元羧酸应减少使用或排除。
聚酯多元醇也可以通过内酯与二醇、三醇和/或四醇的加聚反应来制备。内酯的合适实例包括己内酯、丁内酯和戊内酯。二醇的合适实例是乙二醇、丁二醇、二乙二醇、三乙二醇、聚亚烷基二醇(诸如聚乙二醇、1,2-丙二醇、1,3-丙二醇、2-甲基1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、1,6-己二醇、新戊二醇、3-甲基1,5-戊二醇和其任意组合)。三醇的合适实例包括三羟甲基丙烷和丙三醇。四醇的合适实例包括赤藓醇和季戊四醇。
聚氨基甲酸酯预聚物是以所属领域的一般技术人员所熟知的任何方式来制备的,包括缩聚反应。聚氨基甲酸酯预聚物优选是NCO基封端的预聚物。有机溶剂优选不用于制备聚氨基甲酸酯预聚物。
在制备本发明的聚氨基甲酸酯分散体的实践中,优选在添加水之前将离子型表面活性剂引入聚氨基甲酸酯预聚物中,但是在添加聚氨基甲酸酯预聚物之前将表面活性剂装入水中并不在本发明的范围之外。
按聚氨基甲酸酯分散体的总干重计,离子型表面活性剂是0.5干重%到10干重%、优选1干重%到8干重%且更优选1.5干重%到6干重%。
离子型表面活性剂优选是阴离子型的。阴离子型表面活性剂的合适实例包括磺酸盐、磷酸盐、羧酸盐和其任意组合。阴离子型表面活性剂优选是磺酸盐,诸如十二烷基苯磺酸钠,十二烷基磺酸钠,十二烷基二苯醚二磺酸钠,正癸基二苯醚二磺酸钠,十二烷基苯磺酸异丙胺盐和己基二苯醚二磺酸钠。阴离子型表面活性剂更优选是十二烷基苯磺酸钠。
为了达成扩链目的,添加离子型表面活性剂和水之后,接着添加0.1干重%到8干重%、优选0.2干重%到6干重%且更优选0.5干重%到5干重%多胺(按聚氨基甲酸酯分散体的总干重计)。
多胺优选是二胺,其中每个胺基是伯胺或仲胺。二胺的合适实例包括乙二胺、1,2-和1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、异佛尔酮二胺和其任意组合。
聚氨基甲酸酯分散体的固体含量优选是25%到60%、优选30%到55%且更优选35%到50%。
环氧树脂
将环氧树脂添加到聚氨基甲酸酯分散体中,在搅拌下形成稳定的混合物。
环氧树脂是具有至少2个、优选2到4个且更优选2个环氧基团的化合物。环氧树脂可以通过使含有环氧基团的化合物与二醇或多元醇反应来获得。含有环氧基团的化合物的合适实例包括在与环氧基团相邻的碳原子上被卤原子(尤其是氯原子)取代的那些含有环氧基团的化合物。表氯醇是优选的含有环氧基团的化合物。这些化合物与二醇或多元醇的反应将形成具有末端环氧基团的环氧树脂。二醇或多元醇优选是脂族化合物。多元醇是优选的。多元醇的合适实例包括聚二醇(诸如聚乙二醇(PEG)、聚丙二醇(PPG)、聚丁二醇(PBG))、聚二醇共聚物和其组合。脂族多元醇优选是聚乙二醇(PEG)、聚丙二醇(PPG)、其共聚物和其组合。多元醇更优选是聚丙二醇(PPG)。
特别优选的环氧树脂是表氯醇与PPG的反应产物。
合适环氧树脂的数均摩尔重量优选在200与1000g/mol之间,尤其在300与800g/mol之间。
环氧树脂的合适实例可以是从陶氏化学公司(The Dow Chemical Company)商购的D.E.R.TM732环氧树脂、D.E.R.TM734环氧树脂和D.E.R.TM736环氧树脂。
脂族胺交联剂
将脂族胺交联剂添加到聚氨基甲酸酯分散体与环氧树脂的混合物中,在搅拌下制备本发明的粘合剂组合物。
脂族胺交联剂是具有至少两个与环氧基团反应的反应性氢基团的化合物。脂族胺交联剂优选是在水中可乳化、可分散或可溶解的。脂族胺交联剂尤其是在水中可溶解的。
合适的脂族胺交联剂是含有伯或仲氨基、优选伯和仲氨基的脂族胺。
脂族胺交联剂的合适实例是二亚乙基三胺(DETA)、三亚乙基五胺(TEPA)、三亚乙基四胺(TETA)、聚醚胺和其任意组合。
其它添加剂
聚氨基甲酸酯分散体可以进一步包含反应性地结合到聚氨基甲酸酯预聚物主链上的粘合促进剂。粘合促进剂也可作为后添加剂添加到粘合剂组合物中。选择适当的粘合促进剂在所属领域内众所周知,并且按聚氨基甲酸酯预聚物的总干重计,所述粘合促进剂的用量范围是0.1干重%到3干重%、优选0.1干重%到2干重%且更优选0.1干重%到1干重%。
任何粘合促进剂都可以用于本发明中,同时优选使用硅烷粘合促进剂。硅烷粘合促进剂的合适实例包括诸如氨丙基三乙氧基硅烷的氨基硅烷、诸如3-环氧丙氧基丙基三乙氧基硅烷的环氧硅烷和诸如γ-巯基丙基三甲氧基硅烷的巯基硅烷。
由聚氨基甲酸酯粘合剂组合物制成的层压材料
将粘合剂组合物涂覆到包括金属箔、聚酯膜和尼龙膜的衬底的表面上。优选地,将其涂覆到金属箔的表面上。更优选地,金属箔是铝(Al)箔。
随后干燥涂覆粘合剂组合物以形成干燥层。当剩余的水小于涂覆粘合剂组合物的10%时,涂覆粘合剂组合物被认为是干燥的。
将聚乙烯膜的表面覆盖在涂覆粘合剂组合物的干燥层上,从而形成聚乙烯膜-粘合剂-金属箔复合物(复合膜,并且也被称为层压材料)。在不同的应用中,金属箔可以被聚酯膜或尼龙膜所替代。层压材料优选经受机械力以更加紧密地压制膜。优选通过使层压材料在辊之间通过来施加这种机械力。优选加热辊。
层压材料可以是较厚型层压材料的一部分,其包含附加膜和附加粘合剂组合物。附加膜可以与本发明的层压材料中所包含的膜相同或不同,并且可以是层压工业中常用的任何聚合物膜、纸、金属箔。附加粘合剂组合物可以与本发明的粘合剂组合物相同或不同,并且可以是层压工业中的任何常用粘合剂组合物。
实例
I.原材料
单体芳香族二异氰酸酯:
ISONATETM125M异氰酸酯(125M)是从陶氏化学公司商购的纯4,4'-MDI。
聚醚多元醇:
VORANOLTMV1010多元醇(V1010)是聚醚多元醇,并且可以从陶氏化学公司商购。
VORANOLTMCP450多元醇(CP450)是聚醚多元醇,并且可以从陶氏化学公司商购。
VORANOLTM9287A(9287A)是聚醚多元醇,并且可以从陶氏化学公司商购。
CARBOWAXTM聚乙二醇1000(PEG 1000)是聚醚多元醇,并且可以从陶氏化学公司商购。
TERATHANETM聚四亚甲基醚二醇2000(PTMEG 2000)是聚醚多元醇,并且可以从英威达公司(Invista Company)商购。
聚酯多元醇:
HSM-822-3多元醇(HSM)是聚酯多元醇,并且可以从旭川化学(苏州)有限公司(Xuchuan Chemical(Suzhou)Co.Ltd)商购。
XCP-940AD多元醇(XCP)是聚酯多元醇,并且可以从旭川化学(苏州)有限公司商购。
环氧树脂:
D.E.R.TM736是聚二醇二环氧液体树脂,并且可以从陶氏化学公司商购。
脂族胺交联剂:
D.E.H.TM26是从陶氏化学公司商购的脂族胺交联剂。
异氰酸酯交联剂
CR3A是从陶氏化学公司商购的脂族聚异氰酸酯。
基于脂族异氰酸酯的聚氨基甲酸酯分散体:
PRIMALTM粘结剂U-51是基于脂族异氰酸酯的聚氨基甲酸酯分散体,并且可以从陶氏化学公司商购。
其他:
RHODACALTMDS-4表面活性剂(DS-4)是具有23%固体含量的阴离子型表面活性剂,并且可以从罗地亚公司(Rhodia Company)商购。
1,2-丙二胺(PDA)是化学品级纯扩链剂,并且可以从西格玛奥德里奇公司(Sigma-Aldrich Company)商购。
II.测试方法
1.粘接强度(BS)
将由粘合剂组合物制备的层压材料切割成15mm宽的带材以用于在250mm/min十字头速度下使用从斯特朗公司(Instron Corporation)获得的5940系列单立柱台式试验***(5940Series Single Column Table Top System)进行T-剥离测试。在测试期间,用手指轻轻拉动每条带材的尾部以确保尾部与剥离方向保持呈90度。测试每个样品的三条带材并计算平均值。结果以N/15mm为单位。值越高,粘接强度越好。
2.热封强度(HS)
将由粘合剂组合物制备的层压材料热封在140℃密封温度和300N压力下的从Brugger Company获得的HSG-C热封机中1秒,然后冷却并切割成15mm宽的带材以用于在250mm/min十字头速度下使用从斯特朗公司获得的5940系列单立柱台式试验***进行热封强度测试。测试每个样品的三条带材并计算平均值。结果以N/15mm为单位。值越高,热封强度越好。
3.连袋煮沸抗性(BBR)
将由粘合剂组合物制备的层压材料切割成8cm×12cm片材,并通过热制成密封且内部有水的袋子。然后将袋子放入沸水中并放置在那里30分钟,确保在整个煮沸过程中所有袋子都一直浸在水中。完成后,记录隧穿、分层或泄漏的程度。通过测试的样品将不会显示出隧穿、分层或泄漏的迹象。接着打开袋子、倒空并让其冷却,然后切割成15mm宽的带材以测试斯特朗5943机器中的T-剥离粘接强度。测试三条带材以取平均值。
III.实例
1.制备对比聚氨基甲酸酯分散体1到3(对比PU 1到3)和本发明的聚氨基甲酸酯分散体4到6(PU 4到6)
根据表1,将不同量的异氰酸酯添加到多元醇混合物中,并且在65-90℃下反应4-5小时直到所述混合物达到理论上的异氰酸酯基(NCO)含量,并制备聚氨基甲酸酯预聚物。将所制备的聚氨基甲酸酯预聚物转移到塑料罐中,并且将RHODACALTMDS-4表面活性剂添加到塑料罐中,并以2000-3000rpm搅拌1-3分钟。在搅拌下,将5℃去离子水添加到同一罐中以制备均匀分散体。然后缓慢地将1,2-丙二胺(PDA)(20%水溶液)添加到所述分散体中,并以1000-1500rpm搅拌15-30分钟以制备聚氨基甲酸酯分散体。将额外的环氧树脂添加到聚氨基甲酸酯分散体中并搅拌10-15分钟以制备本发明的聚氨基甲酸酯分散体。每种聚氨基甲酸酯分散体的详细组分都列于表1中。
PRIMALTM粘结剂U-51是基于脂族异氰酸酯的聚氨基甲酸酯分散体,并且与或不与5%D.E.R.TM736环氧树脂混合以分别制备对比聚氨基甲酸酯分散体8和7(对比PU 7到8)。
表1
2.制备粘合剂组合物和层压材料
使聚氨基甲酸酯分散体与0.7干重%D.E.H.26环氧固化剂(用于本发明的聚氨基甲酸酯分散体(PU 4-6)和对比聚氨基甲酸酯分散体8(对比PU 8))(按聚氨基甲酸酯分散体的总干重计)或2干重%CR3A交联剂(用于对比聚氨基甲酸酯分散体(对比PU 1-3和7))(按聚氨基甲酸酯分散体的总干重计)混合以形成对比粘合剂组合物1到3和7到8(对比AC 1到3和7到8)和本发明的粘合剂组合物4到6(AC 4到6)。然后将所述粘合剂组合物涂覆到聚对苯二甲酸乙二醇酯(PET)背衬的Al箔上,并在80℃下的烘箱中干燥40秒。接着将涂覆在Al箔上的粘合剂组合物从烘箱中取出并使用从Cheminstruments,Inc获得的HL-101层压机用40um厚的PE膜覆盖(或层压)。使Al箔-粘合剂组合物-PE膜层压材料在50℃下固化48小时并测试。
IV.结果
表2
本发明的粘合剂组合物4具有与对比粘合剂组合物1相同的聚氨基甲酸酯组合物,本发明的粘合剂组合物5具有与对比粘合剂组合物2相同的聚氨基甲酸酯组合物,并且本发明的粘合剂组合物6具有与对比粘合剂组合物3相同的聚氨基甲酸酯组合物。所有本发明的粘合剂组合物都包含建议的环氧树脂和建议的脂族胺交联剂,而所有对比粘合剂组合物却都不包含。之后,每一组都比较环氧树脂与脂族胺交联剂对粘合剂组合物的影响。如表2所示,本发明的粘合剂组合物4与对比粘合剂组合物1相比较,本发明的粘合剂组合物5与对比粘合剂组合物2相比较,以及本发明的粘合剂组合物6与对比粘合剂组合物3相比较,所有组合物都具有显著改进的粘接强度、热封强度和连袋煮沸抗性。结果表明环氧树脂和脂族胺交联剂在本发明中起到非常重要的作用。
改进的粘合剂性能不仅仅是因为选择了环氧树脂和交联剂,而且还因为选择了聚氨基甲酸酯组合物。
对比粘合剂组合物8包含PRIMALTM粘结剂U-51,一种可商购的聚氨基甲酸酯分散体,其包含脂族异氰酸酯、建议的环氧树脂和建议的交联剂,而对比粘合剂组合物7仅包含PRIMALTM粘结剂U-51和未建议的交联剂。如表2所示,与对比粘合剂组合物7相比,对比粘合剂组合物8并没有显示出改进的粘接强度、热封强度和连袋煮沸抗性。结果表明选择聚氨基甲酸酯组合物的重要性。
Claims (15)
1.一种粘合剂组合物,按所述粘合剂组合物的总干重计,其包含70干重%到96干重%聚氨基甲酸酯分散体、1干重%到20干重%环氧树脂和0.5干重%到15干重%脂族胺交联剂。
2.根据权利要求1所述的粘合剂组合物,其中所述聚氨基甲酸酯分散体包含聚氨基甲酸酯预聚物,并且按所述聚氨基甲酸酯分散体的总干重计,包含0.5干重%到10干重%离子型表面活性剂和0.1干重%到8干重%多胺。
3.根据权利要求2所述的粘合剂组合物,其中按所述聚氨基甲酸酯预聚物的总干重计,所述聚氨基甲酸酯预聚物包含10干重%到40干重%单体芳香族二异氰酸酯和20干重%到85干重%聚醚多元醇作为聚合单元。
4.根据权利要求3所述的粘合剂组合物,其中按所述聚氨基甲酸酯预聚物的总干重计,所述聚氨基甲酸酯预聚物进一步包含0.1干重%到30干重%聚酯多元醇作为聚合单元。
5.根据权利要求3所述的粘合剂组合物,其中所述单体芳香族二异氰酸酯的分子量Mw小于500g/mol。
6.根据权利要求3所述的粘合剂组合物,其中所述单体芳香族二异氰酸酯选自二苯基甲烷二异氰酸酯、甲苯二异氰酸酯和其组合。
7.根据权利要求3所述的粘合剂组合物,其中所述聚醚多元醇的分子量Mw是400到4000g/mol,并且官能度是1.8到4。
8.根据权利要求4所述的粘合剂组合物,其中所述聚酯多元醇的分子量Mw是400到4000g/mol,并且官能度是1.8到4。
9.根据权利要求2所述的粘合剂组合物,其中所述离子型表面活性剂选自磺酸盐、磷酸盐、羧酸盐和其组合。
10.根据权利要求1所述的粘合剂组合物,其中所述聚氨基甲酸酯分散体的固体含量是25%到60%。
11.根据权利要求1所述的粘合剂组合物,其中所述环氧树脂是具有至少2个环氧基团的化合物。
12.根据权利要求1所述的粘合剂组合物,其中所述环氧树脂可以通过使表氯醇与脂族二醇或多元醇反应来获得。
13.根据权利要求12所述的粘合剂组合物,其中所述多元醇是聚丙二醇。
14.根据权利要求1所述的粘合剂组合物,其中所述脂族胺交联剂选自二亚乙基三胺、三亚乙基五胺、三亚乙基四胺、聚醚胺和其任意组合。
15.一种层压材料,其包含权利要求1所述的粘合剂组合物。
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CN114207074A (zh) * | 2019-07-25 | 2022-03-18 | 洛德公司 | 热塑性聚氨酯用单组分粘合剂 |
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EP3694898A4 (en) | 2017-10-12 | 2021-07-14 | Swimc LLC | POLYURETHANE COATING COMPOSITION |
WO2021173301A2 (en) * | 2020-02-27 | 2021-09-02 | Illinois Tool Works Inc. | Heat transfer label and process for the use thereof |
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CN113490702A (zh) * | 2018-12-03 | 2021-10-08 | 洛德公司 | 用于可浇铸聚氨酯的粘合剂 |
CN113490702B (zh) * | 2018-12-03 | 2023-10-27 | 洛德公司 | 用于可浇铸聚氨酯的粘合剂 |
CN114207074A (zh) * | 2019-07-25 | 2022-03-18 | 洛德公司 | 热塑性聚氨酯用单组分粘合剂 |
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RU2018117539A3 (zh) | 2019-11-11 |
BR112018006395B1 (pt) | 2022-05-31 |
EP3368628A4 (en) | 2019-05-22 |
TWI734703B (zh) | 2021-08-01 |
CN108138021B (zh) | 2021-05-04 |
TW201718812A (zh) | 2017-06-01 |
MX2018004384A (es) | 2018-05-11 |
JP6681978B2 (ja) | 2020-04-15 |
EP3368628B1 (en) | 2022-01-26 |
BR112018006395A2 (pt) | 2018-10-09 |
JP2018538375A (ja) | 2018-12-27 |
AR106382A1 (es) | 2018-01-10 |
RU2018117539A (ru) | 2019-11-11 |
EP3368628A1 (en) | 2018-09-05 |
WO2017070820A1 (en) | 2017-05-04 |
US20180298253A1 (en) | 2018-10-18 |
RU2707345C2 (ru) | 2019-11-27 |
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