CN114846041A - 导热聚氨酯粘合剂组合物 - Google Patents
导热聚氨酯粘合剂组合物 Download PDFInfo
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- CN114846041A CN114846041A CN202080085078.1A CN202080085078A CN114846041A CN 114846041 A CN114846041 A CN 114846041A CN 202080085078 A CN202080085078 A CN 202080085078A CN 114846041 A CN114846041 A CN 114846041A
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- Prior art keywords
- adhesive composition
- component
- composition according
- isocyanate
- gamma
- Prior art date
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- 239000012948 isocyanate Substances 0.000 claims description 11
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 5
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Abstract
本发明涉及具有优异的机械性能以及老化后改善的性能的导热聚氨酯粘合剂组合物和它的制备方法。此外,本发明涉及制造包含所述导热聚氨酯粘合剂组合物的制品的方法和通过所述方法可获得的制品。
Description
技术领域
本发明涉及具有优异的机械性能以及老化后改善的性能的导热聚氨酯粘合剂组合物和它的制备方法。此外,本发明涉及制造包含所述导热聚氨酯粘合剂组合物的制品的方法和通过所述方法可获得的制品。
背景技术
导热的粘合剂用于其中必须将部件固定在结构上并且其中必须将热量从所述部件中转移的若干应用中。实例有汽车工业中的电子器件或应用,特别是用于在电动交通中的电力存储的电池的粘合。对于高热导率,需要高填充等级,这通常是与未固化的粘合剂的高拉伸强度、高拉伸伸长率和可接受粘度对立的特征。对于目标应用,长寿命和确保的可靠性是强制性的。对于电动车辆中的电力存储,将模块与冷却板粘合,并且需要确保在宽的工作温度范围内的安全和可靠的性能。
然而,在使用导热的但电绝缘的填料例如氧化铝或氢氧化铝以用于高热导率时,需要非常高的填料含量。这些高填充等级强烈地降低了导热粘合剂的机械性能和流变性能。
已经尝试在聚合物组合物中使用经表面处理的颗粒。
例如,JP 2008127212 A公开了用膦酸酯化合物作为聚合引发剂对氧化铝颗粒进行表面处理,以接枝聚苯乙烯。
JP 2003171120 A公开了硅烷偶联剂,该偶联剂用于将氢氧化铝加入到人造大理石中以获得阻燃性和期望的色调。
CN 102115619 B公开了通过聚丙烯酸树脂涂层来表面改性氧化铝以用作聚烯烃中的高性能填料的方法。
WO 200827561 A1公开了氧化铝颗粒的硅烷表面处理的方法,该方法允许控制在聚酯、聚苯乙烯和聚丙烯酸树脂中所使用的调色剂中的金属氧化物颗粒添加剂的摩擦电荷性质和耐湿性。
而且,已经尝试开发具有改善的粘合强度和伸长率的聚氨酯粘合剂。
WO 2018210568 A1公开了用作粘合剂/密封材料,特别是用作胶合各种基材的粘合剂的粘结剂体系,该粘结剂体系包含作为树脂组分的特定多元醇混合物,所述多元醇混合物包含至少一种基于脂肪酸二聚体、脂肪酸三聚体或由它们衍生的醇的聚酯和至少一种作为树脂组分的聚异氰酸酯和/或NCO-封端的聚氨酯预聚物。
US 8399595 B2公开了两部分组合物,该组合物包含了含有异氰酸酯官能团的组分、异氰酸酯反应性组分、一种或多种具有两个或更多个异氰酸酯反应性基团且分子量为120或更小的低分子量化合物、一种或多种用于异氰酸酯官能团与异氰酸酯反应性基团的反应的催化剂,其中所述催化剂可位于含异氰酸酯官能团的组分或异氰酸酯反应性组分中。
US 9637668B2公开了双组分聚氨酯粘合剂,该粘合剂在特别低的玻璃化转变温度下具有高强度和弹性,适合作为结构粘合剂。该粘合剂含有一定比率的三醇、二醇、聚胺、聚异氰酸酯和具有异氰酸酯基团的聚氨酯聚合物,和Fe(III)或Ti(IV)或Zr(IV)或Hf(IV)螯合络合物催化剂。
因此,本发明的目的是通过提供有利组合上述性能的且适合用于电动车辆中的粘合剂组合物来克服上述缺陷。
发明内容
令人惊讶地发现,本发明的目的可以通过使用双组分聚氨酯粘合剂组合物来解决,所述组合物包含经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料。
因此,本发明的第一目的是包含组分A和组分B的粘合剂组合物,
其中所述组分A包含:
A1)多元醇;
A2)扩链剂;和
A3)经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料,并且
其中所述组分B包含至少一种异氰酸酯(NCO)-封端的化合物。
附图说明
图1是示出根据实施例1的固化的粘合剂产品的断裂面的扫描电子显微镜图像。
图2是示出根据对比例1的固化的粘合剂产品的断裂面的扫描电子显微镜图像。
具体实施方式
除非另外说明,否则如果在本文中提及聚合物的分子量,则该提及是指的数均分子量Mn。聚合物的数均分子量Mn可以例如通过根据DIN 55674的凝胶渗透色谱法(GPC)以THF作为洗脱剂来测定。如果没有另外说明,则所有给出的分子量是通过用聚苯乙烯标准物校准的GPC测定的那些。平均分子量Mw也可以通过GPC测定,如针对Mn所述的。
组分A
本发明粘合剂组合物的组分A包含A1)多元醇,A2)扩链剂,和A3)经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料。
通常,对于在粘合剂组合物中所使用的多元醇的分子量没有限制,只要它对该粘合剂组合物的性能和固化的粘合剂的性能没有负面影响。在本发明的优选实施方案中,所述多元醇具有700至12,000g/mol、特别是1,000至10,000g/mol的分子量Mn。甚至更优选地,所述多元醇是聚醚多元醇,优选地聚醚二醇,所述聚醚二醇优选地包含伯羟基或者伯羟基与仲羟基的混合物。合适的聚醚多元醇的实例有聚氧亚烷基多元醇,例如聚乙二醇、聚丙二醇、聚四亚甲基二醇和聚亚丁基二醇。而且,所列聚氧亚烷基多元醇的均聚物或共聚物以及它们的混合物适合于本发明的目的。特别合适的共聚物是包含选自以下的化合物与选自环氧乙烷、环氧丙烷和环氧丁烷的至少一种化合物的加合物的那些:乙二醇、丙二醇、二甘醇、丙二醇、三甘醇、2-乙基己二醇-1,3-甘油、三羟甲基丙烷、三羟甲基乙烷、三(羟基苯基)丙烷、三羟乙基胺和三异丙胺。
这样的多元醇是本领域熟知的。适用于本发明的多元醇的实例以商品名Lupranol系列从BASF商购,以Acclaim系列从Arcol商购和以Desmophen系列从Covestro商购。
在优选的实施方案中,聚醚多元醇是乙二醇封端的聚乙二醇/聚丙二醇二醇。
在本发明的优选实施方案中,基于组分A的总重量,聚醚多元醇在组分A中以至少5重量%、优选地10重量%至35重量%的量存在。在多元醇的量范围内,可以改善粘合剂组合物的粘合性能。
本发明粘合剂组合物出人意料地显示出性能的期望组合,特别是在高体积电阻率下的高热导率与优异的机械性能和粘合基材老化后的改善搭接剪切强度的组合。出人意料地发现,这组性能可以通过将在双组分聚氨酯粘合剂组合物中的经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料与具有特定分子量的多元醇组合来实现。
经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料包含导热无机填料和在所述填料表面上的异氰酸酯反应性基团。在一个实施方案中,所述导热无机填料选自金属氧化物、金属氢氧化物、金属硅酸盐、金属硫化物和它们的组合。
待用作填料的合适金属氧化物的实例有:选自以下的金属的氧化物,锡、铟、锑、铝、钛、铁、镁、锌、稀土金属、碱金属;Mg、Ca、Sr和Ba的氧化物;混合金属氧化物和它们的混合物。
待用作填料的金属氢氧化物的实例有:选自以下的金属的氢氧化物,锡、铟、锑、铝、钛、铁、镁、锌、稀土金属、碱金属;Mg、Ca、Sr和Ba的氢氧化物;混合金属氢氧化物和它们的混合物。
待用作填料的金属硅酸盐的实例有:选自以下的金属的硅酸盐,锡、铟、锑、铝、钛、铁、镁、锌、稀土金属、碱金属;Mg、Ca、Sr和Ba的硅酸盐;混合金属硅酸盐和它们的混合物。
待用作填料的金属硫化物的实例有:选自以下的金属的硫化物,锡、铟、锑、铝、钛、铁、镁、锌、稀土金属、碱金属;Mg、Ca、Sr和Ba的硫化物;混合金属硫化物和它们的混合物。
在优选的实施例中,导热无机填料选自金属氧化物例如氧化铝,和金属硅酸盐例如硅酸铝。
经表面处理的导热无机填料在填料的表面上具有异氰酸酯反应性基团。对导热无机填料的表面上的异氰酸酯反应性基团没有限制。优选地,所述异氰酸酯反应性基团选自羟基、氨基、羧基、硫醇基、环氧基和它们的组合。更优选地,异氰酸酯反应性基团是氨基烷氧基硅烷或环氧化的烷氧基硅烷的水解残基。
氨基烷氧基硅烷的实例有,3-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-氨基丁基三乙氧基硅烷、N-甲基-3-氨基-2-甲基丙基三甲氧基硅烷、N-乙基-3-氨基-2-甲基丙基三甲氧基硅烷、N-乙基-3-氨基-2-甲基丙基二乙氧基甲基硅烷、N-乙基-3-氨基-2-甲基丙基三乙氧基硅烷、N-乙基-3-氨基-2-甲基丙基甲基二甲氧基硅烷、N-丁基-3-氨基-2-甲基丙基三甲氧基硅烷、3-(N-甲基-2-氨基-1-甲基-1-乙氧基)-丙基三甲氧基硅烷、N-乙基-4-氨基-3,3-二甲基丁基二甲氧基甲基硅烷、N-乙基-4-氨基-3,3-二甲基丁基三甲氧基硅烷、N-(环己基)-3-氨基丙基三甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基三甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基三乙氧基硅烷、N-(2-氨基乙基)-3-氨基丙基甲基-二甲氧基硅烷、氨基丙基三乙氧基硅烷、二-(3-三甲氧基甲硅烷基-2-甲基丙基)胺和N-(3'-三甲氧基甲硅烷基丙基)-3-氨基-2-甲基丙基三甲氧基硅烷。
环氧化的烷氧基硅烷的实例有,环氧丙氧基甲基甲基二甲氧基硅烷、环氧丙氧基甲基甲基二乙氧基硅烷、α-环氧丙氧基乙基甲基二甲氧基硅烷、α-环氧丙氧基乙基甲基二乙氧基硅烷、β-环氧丙氧基乙基甲基二甲氧基硅烷、β-环氧丙氧基乙基甲基二乙氧基硅烷、α-环氧丙氧基丙基甲基二甲氧基硅烷、α-环氧丙氧基丙基甲基二乙氧基硅烷、β-环氧丙氧基丙基甲基二甲氧基硅烷、β-环氧丙氧基丙基甲基二乙氧基硅烷、γ-环氧丙氧基丙基甲基二甲氧基硅烷、γ-环氧丙氧基丙基甲基二乙氧基硅烷、γ-环氧丙氧基丙基甲基二丙氧基硅烷、γ-环氧丙氧基丙基甲基二丁氧基硅烷、γ-环氧丙氧基丙基甲基二甲氧基乙氧基硅烷、γ-环氧丙氧基丙基乙基二甲氧基硅烷、γ-环氧丙氧基丙基乙基二乙氧基硅烷、γ-环氧丙氧基丙基乙基二丙氧基硅烷、γ-环氧丙氧基丙基乙烯基二甲氧基硅烷、γ-环氧丙氧基丙基乙烯基二乙氧基硅烷、环氧丙氧基甲基三甲氧基硅烷、环氧丙氧基甲基三乙氧基硅烷、α-环氧丙氧基乙基三甲氧基硅烷、α-环氧丙氧基乙基三乙氧基硅烷、β-环氧丙氧基乙基三甲氧基硅烷、β-环氧丙氧基乙基三乙氧基硅烷、α-环氧丙氧基丙基三甲氧基硅烷、α-环氧丙氧基丙基三乙氧基硅烷、β-环氧丙氧基丙基三甲氧基硅烷、β-环氧丙氧基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三丙氧基硅烷、γ-环氧丙氧基丙基三丁氧基硅烷、γ-环氧丙氧基丙基三甲氧基乙氧基硅烷、α-环氧丙氧基丁基三甲氧基硅烷、α-环氧丙氧基丁基三乙氧基硅烷、β-环氧丙氧基丁基三甲氧基硅烷、β-环氧丙氧基丁基三乙氧基硅烷、γ-环氧丙氧基丁基三甲氧基硅烷、γ-环氧丙氧基丁基三乙氧基硅烷、δ-环氧丙氧基丁基三甲氧基硅烷、δ-环氧丙氧基丁基三乙氧基硅烷、(3,4-环氧基环己基)甲基三甲氧基硅烷、(3,4-环氧基环己基)甲基三乙氧基硅烷、β-(3,4-环氧基环己基)乙基三甲氧基硅烷、β-(3,4-环氧基环己基)乙基三乙氧基硅烷、β-(3,4-环氧基环己基)乙基三丙氧基硅烷、β-(3,4-环氧基环己基)乙基三丁氧基硅烷、β-(3,4-环氧基环己基)乙基三甲氧基乙氧基硅烷、γ-(3,4-环氧基环己基)丙基三甲氧基硅烷、γ-(3,4-环氧基环己基)丙基三乙氧基硅烷、δ-(3,4-环氧基环己基)丁基三甲氧基硅烷、δ-(3,4-环氧基环己基)丁基三乙氧基硅烷。
经表面处理的在填料的表面上具有异氰酸酯反应性基团的导热无机填料可以商购,例如以商品名Silatherm和Silatherm Plus系列从Quarzwerke商购,以Martoxid系列从Huber/Hpf Minerals商购,以Aeroxide系列从Evonik商购。可替代地,通过使用本领域技术人员已知的方法,用对应于异氰酸酯反应性基团的偶联剂或表面处理剂即对应的硅烷对导热无机填料进行表面处理,可以制备经表面处理的导热无机填料。例如,通过用氨基乙基三甲氧基硅烷对氧化铝填料进行表面处理,可以制备经表面处理的在该填料表面上具有氨基乙基三甲氧基甲硅烷基的氧化铝填料。
不希望受任何理论束缚,通过加入经表面处理的在填料的表面上具有异氰酸酯反应性基团的导热无机填料,该填料能够与异氰酸酯封端的化合物反应并且可与聚氨酯主链共价键合,从而实现改善的机械性质例如拉伸强度。
通过使用经表面处理的导热无机填料,根据本发明的导热聚氨酯粘合剂组合物可以实现导热填料的较低填充等级,以便于改善导热粘合剂的机械性能和流变性能。根据本发明,基于组分A的总重量,经表面处理的导热无机填料在组分A中以不大于95重量%、优选地10重量%至90重量%、更优选地45重量%至85重量%、特别是45重量%至65重量%的量存在。
如果填料的量保持在上述范围内,则可以改善粘合剂组合物的热导率而基本上不影响体积电阻率。
粘合剂组合物的组分A进一步包含扩链剂。通常,扩链剂是用以改性给定聚合物主链的低分子量分子。优选地,所述扩链剂具有60至600g/mol、更优选地60至500g/mol的分子量Mn。在优选的实施方案中,所述扩链剂是二醇,特别是具有9个或更少碳原子的线性的或枝化的二醇。在特别优选的实施方案中,所述扩链剂选自1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、3-甲基-1,5-戊二醇、1,6-己二醇、1,9-壬二醇、乙二醇、聚乙二醇、丙二醇、聚丙二醇、新戊二醇、聚丁二醇、环己烷-1,2-二醇、环己烷-1,4-二醇、1,4-二(羟甲基)环己烷和二聚体二醇(dimer diols)(例如来自Croda的Pripol系列)和它们的混合物。
在另外的优选的实施方案中,基于组分A的总重量,扩链剂在组分A中以至少0.1重量%的量,优选地以2重量%至8重量%的量存在。出人意料地发现,通过改变组分A中的扩链剂的量根据需要可以调整本发明的粘合剂组合物的机械性能。
在优选的实施方案中,多元醇和扩链剂在组分A中以20:1至4:1、优选地10:1至5:1的重量比存在。
组分B
本发明的粘合剂组合物的组分B包含至少一种异氰酸酯封端的化合物。在本发明的优选实施方案中,组分B包含脂族或芳族的NCO-封端的化合物,和优选地芳族(聚)异氰酸酯和/或(聚)异氰酸酯预聚物的混合物。
在优选的实施方案中,NCO-封端的化合物选自1,5-亚萘基二异氰酸酯(NDI)、2,4'-或4,4'-二苯基甲烷二异氰酸酯(MDI)、甲代亚苯基二异氰酸酯(TDI)的异构体、亚甲基三苯基三异氰酸酯(MIT)、水合的MDI(H12MDI)、四甲基亚二甲苯基二异氰酸酯(TMXDI)、1-异氰酸酯基甲基-3-异氰酸酯基-1,5,5-三甲基环己烷(IPDI)、亚二甲苯基二异氰酸酯(XDI)、己烷-1,6-二异氰酸酯(HDI)、五亚甲基二异氰酸酯、二环己基甲烷二异氰酸酯以及它们的二聚体、三聚体、低聚物和多聚物。
合适的(聚)异氰酸酯预聚物是包含OH基团和/或NH基团的化合物与过量的聚异氰酸酯的反应产物。合适的预聚物可以例如通过使如上所述的二醇与过量的如上所述的异氰酸酯反应来获得。
在特别优选的实施方案中,NCO-封端的化合物是MDI异构体的混合物。在优选的实施方案中,基于组分B的总重量,组分B包含至少10重量%、更优选地至少25重量%的NCO-封端的化合物。在特别优选的实施方案中,组分B包含10重量%至90重量%、特别是25重量%至40重量%的NCO-封端的化合物。
根据本发明的组合物可进一步包含添加剂。这些添加剂可用于影响组合物的性能,例如机械性能和热导率。优选地,所述一种或多种添加剂选自另外的填料、颜料、流变改性剂、干燥剂、阻燃剂、固化剂、表面活性剂和消泡剂。
在优选的实施方案中,基于组分A和/或B的总重量,存在于组分A和/或B中的添加剂的量为0至95重量%,优选地10至90重量%,更优选地15至75重量%。
除了粘合剂组合物的热导率和机械性能之外,还必须考虑其它特征,例如可加工性。特别地,粘合剂组合物的可固化性必须适应于相应的应用。出人意料地发现,在组分A与组分B的混合比在一定范围内时,有利地平衡了本发明粘合剂组合物的机械性能。因此,其中组分A与组分B的混合重量比为10:1至1:5、优选地10:1至1:1.1、特别是5:1至1:1的本发明的实施方案是优选的。
为了在工业应用中是可加工的,粘合剂组合物需要具有允许容易地且精确地施加的粘度。因此,其中根据本发明的粘合剂组合物具有不大于10,000Pas、优选地不大于1,000Pas、特别是30至1,000Pas的粘度的实施方案是优选的,所述粘度使用布鲁克菲尔德RVDV-II+P,心轴RV T-F在20℃下以10rpm测定。
本发明的粘合剂组合物是导热的。在优选的实施方案中,粘合剂组合物表现出至少0.8W/mK、优选地1.0至3.0W/mK的热导率,该热导率在25℃下根据ISO 22007-2测定。出人意料地发现,如果在上述范围内选择粘合剂组合物的热导率,则可以实现热导率与粘合性之间的有利平衡。另外,在上述范围内的热导率使得粘合剂组合物特别适合用于能量存储设备的组件中。
本发明的另外的目的是通过固化根据本发明的粘合剂组合物可获得的固化的粘合剂产品。通过本领域技术人员熟知的常规方法,例如用辐射如UV光的处理、暴露于湿气、诱导和/或加热,可以进行本发明的粘合剂组合物的固化。
通常,粘合剂组合物的热导率是以粘合剂的成本和粘合剂的机械性能为代价来实现。出人意料地发现,本发明的固化的粘合剂组合物不仅表现出优异的热导率,还具有有利的机械性能。
本发明的固化的粘合剂产品表现出至少7.0MPa、优选地7.0至15MPa的拉伸强度,该拉伸强度根据DIN EN ISO 527在23℃下测定。出人意料地发现,在选择所述数值以处于上述范围内时,固化的组合物显示出有利的内聚强度。
在本发明的另外的优选的实施方案中,固化的粘合剂组合物表现出至少40MPa的拉伸模量,所述拉伸模量根据DIN EN ISO 527在23℃下测定。出人意料地发现,如果拉伸模量在上述范围内,则固化的粘合剂显示出柔韧性,该柔韧性允许吸收机械冲击而不显著影响拉伸强度。
在本发明的还另外优选的实施方案中,固化的粘合剂组合物表现出至少50%的断裂拉伸伸长率,该伸长率根据DIN EN ISO 527在23℃下测定。
在本发明的还另外优选的实施方案中,固化的粘合剂组合物表现出至少5.0MPa、优选地5.0至20MPa的搭接剪切强度,该剪切强度根据DIN EN 1465以用异丙醇清洁的具有0.3mm间隙的喷砂铝基材测定。
在本发明的还另外优选的实施方案中,固化的粘合剂组合物表现出至少3.0MPa、优选地3.0至20MPa的交替气候老化(-30℃至+90℃,20个循环,持续10天)之后的搭接剪切强度,该剪切强度根据DIN EN 1465用喷砂铝基材测定。
在优选的实施方案中,固化的粘合剂组合物表现出至少0.8W/mK、优选地1.0至3.0W/mK的热导率,该热导率在25℃下根据ISO 22007-2测定。
本发明的粘合剂组合物特别适合用于能量存储设备的组件中。因此重要的是,固化的粘合剂组合物不显示任何显著的导电性。因此,在优选的实施方案中,固化的粘合剂组合物具有高的体积电阻率,所述体积电阻率优选大于109Ωm,特别是大于1010Ωm,所述体积电阻率根据DIN EN 62631-3-1测定。
本发明的另外的目的是用于制备本发明的粘合剂组合物的方法。根据本发明的方法包括以下步骤:
a)提供所述组分A和组分B;和
b)将组分A与组分B混合以获得所述粘合剂组合物。
在优选的实施方案中,根据本发明的方法包括以下步骤:
a)提供至少一种多元醇;
b)提供至少一种扩链剂;
c)提供经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料;
d)任选地提供添加剂;
e)混合所提供的组分以获得组分A;
f)提供所述异氰酸酯封端的化合物和任选存在的添加剂作为组分B;和
g)将所述组分A与所述组分B混合以获得所述粘合剂组合物。
本发明的另外的目的是使用根据本发明的粘合剂组合物制造制品的方法。根据本发明的方法包括以下步骤:
i)将根据本发明的粘合剂组合物施加到待粘合的第一基材的表面上;
ii)使经所述粘合剂组合物处理的待粘合的所述第一基材的表面与待粘合的第二基材接触;和
iii)使所述粘合剂组合物固化以获得期望的制品。
在优选的实施方案中,通过施加压力来进行待粘合的第一基材与待粘合的第二基材的接触。
根据本发明的方法特别适合用于温度敏感设备的制造。因此,在优选的实施方案中,在20至100℃、优选地23至70℃的温度下,将粘合剂组合物施加到第一基材的表面上。
另外的目的是根据本发明的制造方法可获得的制品。优选地,根据本发明的制品包含根据本发明的固化的粘合剂组合物。
根据本发明的粘合剂组合物可以应用于各种技术领域中,并且特别适合于热敏的物体,特别是其中产生热量的物体的制造中。因此,本发明的另外的目的是本发明的粘合剂组合物用于以下中的用途:用于管中,优选地用于冷却旋管中;用于电子部件,优选地发光设备、计算机设备、移动电话、平板电脑、触摸屏、汽车技术、高保真系统和音频系统中;用于太阳能加热的供暖设备中的热管与水箱之间的接头中;用于燃料电池和风力涡轮机中;用于计算机芯片的制造中;用于照明设备中;电池;用于外壳中;用于冷却器中;热交换设备;线材;电缆;加热丝;家用电器例如冰箱和洗碗机;空调;蓄电池;变压器;激光器;功能性服装;汽车座椅;医用设备;消防;电动机;飞机和火车。
将通过以下实施例更详细地示例说明本发明,所述实施例不应理解为限制本发明的概念。
实施例
在实施例中使用以下材料。
多元醇4000是具有约4,000的Mn的乙二醇封端的聚乙二醇/聚丙二醇二醇的市售产品。
扩链剂是3-甲基-1,5-戊二醇。
未经表面处理的氧化铝以商品名Martoxid TM 1250从Huber Martinswerk商购获得。
烷基硅烷处理的氧化铝以商品名Martoxid TM 2250从Huber Martinswerk商购获得。
氨基硅烷处理的氧化铝以商品名Martoxid TM 4240从Huber Martinswerk商购获得。
未经表面处理的硅酸铝以商品名Silatherm 1466-506从Quarzwerke商购获得。
环氧硅烷处理的硅酸铝以商品名Silatherm 1466-506EST从Quarzwerke商购获得。
催化剂是二月桂酸二辛基锡。
其它填料包括石墨、氮化硼、沸石和疏水性热解法二氧化硅,都是市售产品。
如实施例和对比例制备两部分聚氨酯粘合剂组合物。根据表1中的组分和量,通过以下方式来配制所述组合物的组分A以获得组分A:用Speed混合器DAC400(来自FlackTekInc.)充分混合除导热填料之外的所有组分直至混合物完全溶解,然后将所述导热填料加入到所述混合物中并充分混合。
所述组合物的组分B含有基于4,4'-MDI的改性异氰酸酯、60重量%的在组分A中所使用的相应氧化铝或硅酸铝、3重量%的石墨、3重量%的沸石和1重量%的疏水性热解法二氧化硅。通过使用Speed混合器DAC400(来自FlackTek Inc.)将所述组分B充分混合。在施加到基材上之前,将组分A与组分B以提供1.05的异氰酸酯指数的重量比混合在一起。NCO指数在此定义为所用异氰酸酯的当量相对于NCO与NCO-反应性官能团1:1反应所需的理论当量的比率。
表1.粘合剂组合物的组分A的配方(按克计)
性能评估
对于在80℃下固化的粘合剂产品,分别在23℃下测定在表2至表6中的以下性能。
表2.机械强度和粘度的测试结果
表3.热导率的测试结果
表4.体积电阻率的测试结果
项目 | 实施例1 | 实施例2 | 实施例3 | 对比例1 | 对比例3 |
体积电阻率[10<sup>10</sup>Ωm] | 4.3 | 4.2 | 3.1 | 1.4 | 3.8 |
表5.搭接剪切强度的测试结果
表6.通过SEM图像评价破碎的拉伸试样断裂面的填料-聚合物界面的主要失效模式
项目 | 实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 对比例1 | 对比例2 | 对比例3 |
失效模式 | 内聚 | 内聚 | 内聚 | 内聚 | 内聚 | 粘合 | 粘合 | 粘合 |
从表2至表6可以看出,本发明实现了良好的热导率与优异的机械性能和老化后的良好性能的组合。具体地,具有较低填料含量的经表面处理的氧化铝或硅酸铝的所有本发明实施例在机械性能和热导率方面表现出优异的性能。
然而,相比于本发明实施例,具有未经处理的氧化铝或硅酸铝的对比例1和3显示出更低的搭接剪切强度和/或老化的搭接剪切强度。此外,对比例2含有经烷基硅烷处理的在填料表面上不具有异氰酸酯反应性基团的氧化铝,相比于本发明实施例,对比例2表现出更差的拉伸模量和拉伸强度。
此外,通过破碎的拉伸试样的填料-聚合物界面的断裂面的SEM图像,进一步证明了粘合剂组合物中所含有的经表面处理的在所述表面上具有异氰酸酯反应性基团的导热无机填料的显著影响,如图1和图2以及表6中所示。在本发明的实施例中,断裂图案主要显示出固化的粘合剂的内聚失效,同时所有对比例显示出在填料与固化的粘合剂的界面处所发生的粘合失效。
Claims (15)
1.粘合剂组合物,其包含组分(A)和组分(B),其中所述组分(A)包含:
A1)多元醇;
A2)扩链剂;和
A3)经表面处理的导热无机填料,所述导热无机填料在所述表面上具有异氰酸酯反应性基团,并且
其中所述组分(B)包含异氰酸酯封端的化合物。
2.根据权利要求1所述的粘合剂组合物,其中所述多元醇是聚醚多元醇,优选地聚醚二醇,所述聚醚二醇优选地包含伯羟基或者伯羟基与仲羟基的混合物。
3.根据权利要求1或2所述的粘合剂组合物,其中所述多元醇具有700至12,000g/mol、优选地1,000至10,000g/mol的分子量Mn。
4.根据权利要求1至3中的任意一项所述的粘合剂组合物,其中所述扩链剂是二醇,优选地选自1,2-丙二醇、1,3-丙二醇、2-甲基-1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、3-甲基-1,5-戊二醇、1,6-己二醇、1,9-壬二醇、乙二醇、聚乙二醇、丙二醇、聚丙二醇、新戊二醇、聚丁二醇、环己烷-1,2-二醇、环己烷-1,4-二醇、1,4-二(羟甲基)环己烷、二聚体二醇和它们的混合物。
5.根据权利要求1至4中的任意一项所述的粘合剂组合物,其中所述扩链剂具有60至600g/mol、优选地70至500g/mol的分子量Mn。
6.根据权利要求1至5中的任意一项所述的粘合剂组合物,其中所述导热无机填料选自金属氧化物、金属氢氧化物、金属硅酸盐、金属硫化物和它们的组合,优选地是氧化铝、氢氧化铝或硅酸铝。
7.根据权利要求1至6中的任意一项所述的粘合剂组合物,其中在所述填料表面上的所述异氰酸酯反应性基团选自羟基、氨基、羧基、硫醇基、环氧基和它们的组合。
8.根据权利要求1至7中的任意一项所述的粘合剂组合物,其中所述异氰酸酯反应性基团是氨基烷氧基甲硅烷基或环氧化的烷氧基甲硅烷基,优选地选自γ-环氧丙氧基丙基三甲氧基甲硅烷基、γ-环氧丙氧基丙基三乙氧基甲硅烷基、γ-环氧丙氧基丙基甲基二甲氧基甲硅烷基、γ-环氧丙氧基丙基甲基二乙氧基甲硅烷基、氨基乙基三甲氧基甲硅烷基、氨基乙基三乙氧基甲硅烷基、氨基丙基三甲氧基甲硅烷基、氨基丙基三乙氧基甲硅烷基、氨基丙基甲基二甲氧基甲硅烷基、氨基丙基甲基二乙氧基甲硅烷基、氨基乙基-γ-氨基丙基-三甲氧基甲硅烷基、亚氨基二(丙基三甲氧基甲硅烷基)和它们的组合。
9.根据权利要求1至8中的任意一项所述的粘合剂组合物,其中所述异氰酸酯封端的化合物是脂族或芳族异氰酸酯封端的化合物,优选地芳族(聚)异氰酸酯和/或芳族(聚)异氰酸酯预聚物的混合物,更优选地亚甲基二苯基二异氰酸酯的异构体的混合物。
10.根据权利要求1至9中的任意一项所述的粘合剂组合物,其中组分A与组分B的质量比为10:1至1:5。
11.根据权利要求1至10中的任意一项所述的粘合剂组合物,其中,基于组分A的总重量,所述经表面处理的导热无机填料以不大于95重量%、优选地10重量%至90重量%、更优选地45重量%至85重量%、特别是45重量%至65重量%的量存在。
12.通过固化根据权利要求1至11中的任意一项所述的粘合剂组合物可获得的固化的粘合剂产品。
13.根据权利要求12所述的固化的粘合剂产品,其中所述产品具有至少0.8W/mK、优选地1.0至3.0W/mK的热导率,所述热导率在25℃下根据ISO 22007-2测定。
14.用于制造根据权利要求1至11中的任意一项所述的粘合剂组合物的方法,所述方法包括:
a)提供所述组分A和所述组分B;和
b)将所述组分A与所述组分B混合以获得所述粘合剂组合物。
15.制造包含至少两个粘合的基材的制品的方法,所述方法包括:
i)将根据权利要求1至11中的任意一项所述的粘合剂组合物施加到待粘合的第一基材的表面上;和
ii)使包含所述粘合剂组合物的待粘合的所述第一基材的表面与待粘合的第二基材接触。
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CN115572363A (zh) * | 2022-09-09 | 2023-01-06 | 天津澳普林特科技股份有限公司 | 一种高导热聚氨酯、制备方法及其用途 |
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CN113736419B (zh) * | 2021-10-19 | 2022-04-12 | 杭州之江新材料有限公司 | 一种双组分聚氨酯导热结构胶及其制备方法 |
WO2023117811A1 (en) | 2021-12-21 | 2023-06-29 | Sika Technology Ag | Injectable thermally conductive curable composition |
WO2023136989A1 (en) * | 2022-01-12 | 2023-07-20 | Ddp Specialty Electronic Materials Us, Llc | Two-component polyurethane adhesive composition |
WO2023178536A1 (en) * | 2022-03-23 | 2023-09-28 | Henkel Ag & Co. Kgaa | Two-component polyurethane based thermal conductive adhesive composition, polyurethane based thermal conductive adhesive and article thereof |
WO2023196365A1 (en) * | 2022-04-06 | 2023-10-12 | Ddp Specialty Electronic Materials Us, Llc | Two-component polyurethane adhesive composition |
WO2023196368A1 (en) * | 2022-04-06 | 2023-10-12 | Ddp Specialty Electronic Materials Us, Llc | Two-component polyurethane adhesive composition |
CN114806486B (zh) * | 2022-05-31 | 2023-05-30 | 韦尔通科技股份有限公司 | 一种导热填料的制备方法及高导热反应型聚氨酯热熔胶组合物 |
CN116515450B (zh) * | 2023-05-16 | 2024-01-30 | 广州市百舜合成材料有限公司 | 一种聚氨酯灌封胶及其制备方法 |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1055703A (zh) * | 1990-04-05 | 1991-10-30 | 明尼苏达州采矿制造公司 | 路面标记材料 |
DE19961973A1 (de) * | 1999-12-22 | 2001-06-28 | Basf Ag | Verfahren zur Herstellung von Polyurethanen mit verbesserter Aushärtung |
JP2005015644A (ja) * | 2003-06-26 | 2005-01-20 | Yokohama Rubber Co Ltd:The | 新規化合物およびそれを含有する硬化性樹脂組成物 |
CN102190881A (zh) * | 2010-02-19 | 2011-09-21 | 市川株式会社 | 抄纸用操作带及其制造方法 |
CN102627937A (zh) * | 2012-03-27 | 2012-08-08 | 合肥工业大学 | 一种双组分导热聚氨酯灌封胶及其制备方法 |
CN102838719A (zh) * | 2012-09-21 | 2012-12-26 | 中国海洋石油总公司 | 高疏水的有机硅—聚氨酯保温复合材料及制备方法 |
CN102876279A (zh) * | 2012-09-17 | 2013-01-16 | 太原市塑料研究所 | 一种非开挖管道修复用聚氨酯胶粘剂及其制备方法 |
CN104789151A (zh) * | 2014-01-22 | 2015-07-22 | 浙江三元电子科技有限公司 | 热熔胶组合物及其制备方法、热熔胶导热片及其制备方法 |
JP5897184B1 (ja) * | 2015-05-12 | 2016-03-30 | サンユレック株式会社 | ポリウレタン樹脂組成物 |
CN105907348A (zh) * | 2016-06-08 | 2016-08-31 | 蚌埠高华电子股份有限公司 | 一种led显示屏用纳米氮化铝改性的复合环氧灌封胶 |
CN106978128A (zh) * | 2017-05-09 | 2017-07-25 | 东莞市普力达光学材料科技有限公司 | 聚氨酯胶粘剂及其制备方法、以及导热胶带 |
CN107488251A (zh) * | 2017-08-01 | 2017-12-19 | 广东工业大学 | 一种水性聚氨酯导热材料及其制备方法 |
CN107513363A (zh) * | 2017-09-27 | 2017-12-26 | 安徽大松树脂有限公司 | 一种耐水阻燃聚氨酯胶黏剂 |
US20170369632A1 (en) * | 2015-03-12 | 2017-12-28 | Henkel Ag & Co. Kgaa | Ultralow Monomer Polyurethanes |
CN107735475A (zh) * | 2015-06-18 | 2018-02-23 | 陶氏环球技术有限责任公司 | 用红外辐射固化的潜伏型双组分聚氨基甲酸酯粘合剂 |
CN109679560A (zh) * | 2018-12-04 | 2019-04-26 | 顺德职业技术学院 | 导热湿气固化有机硅改性阻燃聚氨酯热熔胶及其制备方法 |
WO2019123336A1 (en) * | 2017-12-22 | 2019-06-27 | 3M Innovative Properties Company | Thermally conductive adhesives and articles, and methods of making same |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003171120A (ja) | 2001-11-30 | 2003-06-17 | Sumitomo Chem Co Ltd | 樹脂充填用水酸化アルミニウム及びこれを用いてなる人造大理石用樹脂組成物 |
WO2008027561A2 (en) | 2006-09-01 | 2008-03-06 | Cabot Corporation | Surface-treated metal oxide particles |
JP2008127212A (ja) | 2006-11-16 | 2008-06-05 | Sumitomo Chemical Co Ltd | 表面処理アルミニウム酸化物粒子 |
JP5530355B2 (ja) | 2007-07-23 | 2014-06-25 | ダウ グローバル テクノロジーズ エルエルシー | 使用温度範囲を通して実質的に不変の弾性率gを有する2部分型ポリウレタンの硬化性組成物 |
CN102115619B (zh) | 2009-12-31 | 2013-07-24 | 中国科学院化学研究所 | 对氧化铝进行表面处理的方法 |
EP2706075A1 (de) | 2012-09-11 | 2014-03-12 | Sika Technology AG | Struktureller Polyurethanklebstoff mit tiefer Glasübergangstemperatur |
DE102017208511A1 (de) | 2017-05-19 | 2018-11-22 | Henkel Ag & Co. Kgaa | Polyurethan-basiertes Bindemittel-System |
-
2019
- 2019-12-13 EP EP19216133.9A patent/EP3835332A1/en active Pending
-
2020
- 2020-11-30 KR KR1020227019216A patent/KR20220113383A/ko active Search and Examination
- 2020-11-30 CN CN202080085078.1A patent/CN114846041A/zh active Pending
- 2020-11-30 CA CA3164186A patent/CA3164186A1/en active Pending
- 2020-11-30 WO PCT/EP2020/083843 patent/WO2021115810A1/en active Application Filing
- 2020-11-30 MX MX2022007145A patent/MX2022007145A/es unknown
- 2020-11-30 JP JP2022535725A patent/JP2023505588A/ja active Pending
-
2022
- 2022-05-31 US US17/804,623 patent/US20220290020A1/en active Pending
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1055703A (zh) * | 1990-04-05 | 1991-10-30 | 明尼苏达州采矿制造公司 | 路面标记材料 |
DE19961973A1 (de) * | 1999-12-22 | 2001-06-28 | Basf Ag | Verfahren zur Herstellung von Polyurethanen mit verbesserter Aushärtung |
JP2005015644A (ja) * | 2003-06-26 | 2005-01-20 | Yokohama Rubber Co Ltd:The | 新規化合物およびそれを含有する硬化性樹脂組成物 |
CN102190881A (zh) * | 2010-02-19 | 2011-09-21 | 市川株式会社 | 抄纸用操作带及其制造方法 |
CN102627937A (zh) * | 2012-03-27 | 2012-08-08 | 合肥工业大学 | 一种双组分导热聚氨酯灌封胶及其制备方法 |
CN102876279A (zh) * | 2012-09-17 | 2013-01-16 | 太原市塑料研究所 | 一种非开挖管道修复用聚氨酯胶粘剂及其制备方法 |
CN102838719A (zh) * | 2012-09-21 | 2012-12-26 | 中国海洋石油总公司 | 高疏水的有机硅—聚氨酯保温复合材料及制备方法 |
CN104789151A (zh) * | 2014-01-22 | 2015-07-22 | 浙江三元电子科技有限公司 | 热熔胶组合物及其制备方法、热熔胶导热片及其制备方法 |
US20170369632A1 (en) * | 2015-03-12 | 2017-12-28 | Henkel Ag & Co. Kgaa | Ultralow Monomer Polyurethanes |
JP5897184B1 (ja) * | 2015-05-12 | 2016-03-30 | サンユレック株式会社 | ポリウレタン樹脂組成物 |
CN107735475A (zh) * | 2015-06-18 | 2018-02-23 | 陶氏环球技术有限责任公司 | 用红外辐射固化的潜伏型双组分聚氨基甲酸酯粘合剂 |
CN105907348A (zh) * | 2016-06-08 | 2016-08-31 | 蚌埠高华电子股份有限公司 | 一种led显示屏用纳米氮化铝改性的复合环氧灌封胶 |
CN106978128A (zh) * | 2017-05-09 | 2017-07-25 | 东莞市普力达光学材料科技有限公司 | 聚氨酯胶粘剂及其制备方法、以及导热胶带 |
CN107488251A (zh) * | 2017-08-01 | 2017-12-19 | 广东工业大学 | 一种水性聚氨酯导热材料及其制备方法 |
CN107513363A (zh) * | 2017-09-27 | 2017-12-26 | 安徽大松树脂有限公司 | 一种耐水阻燃聚氨酯胶黏剂 |
WO2019123336A1 (en) * | 2017-12-22 | 2019-06-27 | 3M Innovative Properties Company | Thermally conductive adhesives and articles, and methods of making same |
CN109679560A (zh) * | 2018-12-04 | 2019-04-26 | 顺德职业技术学院 | 导热湿气固化有机硅改性阻燃聚氨酯热熔胶及其制备方法 |
Non-Patent Citations (3)
Title |
---|
EYOB WONDU,等: "Thermal Conductivity and Mechanical Properties of Thermoplastic Polyurethane-/Silane-Modified Al2O3 Composite Fabricated via Melt Compounding", 《POLYMERS》, vol. 11, no. 7, pages 1103, XP055695725, DOI: 10.3390/polym11071103 * |
杨再军,等: "电子封装用聚氨酯灌封胶的研制", 《中国胶粘剂》, vol. 25, no. 6, pages 30 - 34 * |
高旭瑞,等: "光固化水性聚氨酯导热涂层的制备及性能", 《材料保护》, vol. 49, no. 11, pages 26 - 31 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115572363A (zh) * | 2022-09-09 | 2023-01-06 | 天津澳普林特科技股份有限公司 | 一种高导热聚氨酯、制备方法及其用途 |
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