CN115397891A - 具有可辐射交联基团和可湿交联基团的聚硅氧烷 - Google Patents
具有可辐射交联基团和可湿交联基团的聚硅氧烷 Download PDFInfo
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- CN115397891A CN115397891A CN202080099826.1A CN202080099826A CN115397891A CN 115397891 A CN115397891 A CN 115397891A CN 202080099826 A CN202080099826 A CN 202080099826A CN 115397891 A CN115397891 A CN 115397891A
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
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Abstract
本发明涉及由通式(I)RnSiO(4‑n/2的单元组成的有机(聚)硅氧烷(A),其中R选自基团R1、–OR2、Ru、RS和Q,其中R1、R2、Ru和n表示权利要求1限定的烃基,RS表示具有1至18个碳原子的单价硫醇官能化烃基,Q是式(II)‑CR5R6‑NR4R3氮的官能团,其中R3和R4独立地表示氢或具有1至18个碳原子的取代或未取代的烃基,并且R5和R6独立地表示氢或甲基,条件是所述有机(聚)硅氧烷(A)每分子含有至少一个通式(III)Q‑Si(OR7)2O1/2的单元,其中R7如针对R2所定义的;至少1个脂族不饱和基团Ru;和至少2个硫醇官能化基团RS。本发明还涉及制备有机(聚)硅氧烷(A)的方法,以及可湿交联和可辐射交联的有机(聚)硅氧烷混合物(M),其包含有机(聚)硅氧烷(A)。
Description
本发明涉及在暴露于湿气时和通过辐射可交联的有机(聚)硅氧烷,以及涉及包含这些有机(聚)硅氧烷的有机(聚)硅氧烷混合物。
通过这两种不同交联机理固化的有机(聚)硅氧烷组合物通常称为双固化体系并且是已知的。
纯湿固化有机(聚)硅氧烷制剂的问题是这些制剂的固化反应速率取决于水通过表面扩散。在一定的层厚度以上,固化不再与在表面上(例如在几秒内)一样快地发生,这意味着这种类型的可固化有机(聚)硅氧烷制剂不适合用于需要在短时间内实现物质的粘合或密封特性的应用中。相反,可辐射固化的有机(聚)硅氧烷混合物的缺点在于,尽管它们在暴露于直接辐射时迅速固化,但固化在阴影区域中仅缓慢进行。
为了避免这些缺点,因此已尝试将两种类型的交联结合。
例如,已经通过使OH封端的聚硅氧烷与三烷氧基甲硅烷基官能丙烯酸衍生物反应进行尝试。在此例如参考WO17201229A1,其中描述了有机(聚)硅氧烷组合物,该有机(聚)硅氧烷组合物除了丙烯酸官能单元之外,还具有可水解基团,诸如烷氧基。为了足够快速的湿交联,必须向这些体系中加入催化剂。在大多数情况下,这些是具有毒物学问题的锡化合物。
而在这种情况下,光交联是基于丙烯酸类聚合,为此目的已经努力使用自由基诱导的硫醇-烯交联,因为它具有一些优于丙烯酸类交联的优点,例如较少的大气氧抑制和形成更均匀的无张的网络(参见Hoyle,C.E.,Bowman,C.N.,Angew.Chem.122,1584(2010),section2.1.1)。
WO2019/005393和WO2019/028013以举例的方式描述了具有脂族不饱和基团的聚硅氧烷和具有硫醇官能团的聚硅氧烷的混合物,它们中的每一个能够带有可湿交联的烷氧基。在这种情况下,在阴影区域中没有未交联部分的迁移,但是生产两种单独的聚合物的复杂性非常高并且降低了成本效益。此外,交联催化剂的存在是必要的,这可能对混合物的储存稳定性具有不利影响。对于与电子元件接触的情况下的使用,含金属的催化剂由于它们的离子特性特别地是不希望的。
DE4120418A1(WA9033S Wacker Chemie GmbH;于1991年6月20日提交)描述了一种这样的体系,该体系在一种聚合物中包含可湿交联的H-烷氧基甲硅烷基和可辐射交联的硫代烷基和乙烯基。结果,在阴影区域中没有未交联成分的迁移。为了加速湿交联,长链羧酸诸如油酸作为催化剂是足够的,但这些具有腐蚀特性并且对即用型总混合物的储存稳定性产生不利影响。在短时间之后,甚至在封闭的容器中也发生氢气放出,这导致压力的积累和压力释放时的可燃气体混合物。因此,这些混合物构成安全风险。
本发明涉及由通式(I)的单元组成的有机(聚)硅氧烷(A)
RnSiO(4-n/2 (I)
其中
n为0、1、2或3,其中n=0的单元的比例不大于50摩尔%,且n=1的单元的比例不大于60摩尔%,在每种情况下均基于通式(I)的所有单元,
R选自基团R1、–OR2、Ru、RS和Q,其中
R1表示具有1至18个碳原子的单价取代或未取代的烃基,
R2表示氢原子或具有1至6个碳原子的单价取代或未取代的烃基,
Ru表示具有2至18个碳原子的单价脂族不饱和烃基,
RS表示具有1至18个碳原子的单价硫醇官能化烃基,
Q是式(II)的氮官能团
-CR5R6-NR4R3 (II),
其中
R3和R4各自独立地表示氢或具有1至18个碳原子的取代或未取代的烃基,并且
R5和R6各自独立地表示氢或甲基,
条件是所述有机(聚)硅氧烷(A)每分子含有至少一个通式(III)的单元,至少2个脂族不饱和基团Ru;和至少2个硫醇官能化基团RS;
Q-Si(OR7)2O1/2(III)
其中R7如针对R2所定义的。
利用在一个分子中同时含有可湿交联基团和可辐射交联基团的有机(聚)硅氧烷(A),可以生产不需要用于湿交联的催化剂的储存稳定的有机(聚)硅氧烷组合物(M)。
基团R1优选是具有1至18个碳原子的直链或支链的任选取代的烷基和芳基,其可被非相邻的氧原子中断。
基团R1的实例是烷基,诸如甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基或叔戊基、己基(诸如正己基)、庚基(诸如正庚基)、辛基(诸如正辛基、2-乙基-1-己基,和异辛基诸如2,2,4-三甲基戊基)、壬基(诸如正壬基)、癸基(诸如正癸基)、十二烷基(诸如正十二烷基)、十六烷基(诸如正十六烷基);环烷基,诸如环戊基、环己基、环庚基和甲基环己基;芳基,诸如苯基和萘基;烷芳基,诸如邻-、间-和对-甲苯基、二甲苯基和乙基苯基;芳烷基,诸如苄基、2-苯基-1-丙基或α-和β-苯乙基。
取代烃基R1的实例是烷氧基烷基诸如2-甲氧基-1-乙基、甲氧基甲基,卤代烷基诸如氯甲基、3-氯丙基或3,3,3-三氟丙基,和酰氧基烷基诸如乙酰氧基乙基。
特别优选甲基、苯基和3,3,3-三氟丙基,尤其是甲基。
基团R2和R7优选是具有1至6个碳原子的单价任选取代的烷基。基团R2和R7的实例是烷基,诸如甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基,以及取代的基团,诸如2-甲氧基-1-乙基或2-正丁氧基-1-乙基,特别优选甲基、乙基、正丙基和异丙基,尤其是甲基和乙基,非常特别优选乙基,因为其毒性较低。
基团Ru优选是具有至少一个脂族碳-碳多重键且具有2至18个碳原子的烃基,其也可被非相邻的氧原子取代或中断。
基团Ru的实例是乙烯基、烯丙基、1-丙烯-1-基、炔丙基、丙二烯基、正-丁-3-烯基、正-己-5-烯基、正-十一-10-烯基、3-烯丙氧基苯基、4-烯丙氧基苯基、4-烯丙氧基-2-甲基苯基、4-烯丙氧基苄基、4-烯丙氧基苯氧基苯基和丙-2-炔氧基-正丙基,含有内环碳-碳多重键的基团诸如环戊烯基、环己烯基、环庚烯基、环辛烯基、2-环己烯基-1-乙基或2-降冰片烯基乙基。基团Ru优选是乙烯基或烯丙基,更优选是乙烯基。
单价硫醇官能化基团RS优选是硫醇官能化烃基,其可以被非相邻的氧原子中断,并且具有1至18个碳原子和至少一个SH基团。
基团RS的实例是-(CH2)3SH、-(CH2)6SH、-(CH2)4CH(SH)CH3、2-(3-巯基-1-环己基)-1-乙基、2-(3,4-二巯基-1-环己基)-1-乙基、-(CH2)3O(CH2)3SH、-(CH2)3OCH2CH(SH)CH2SH、-(CH2)3OCH2CH(SH)CH3、-(CH2)3OOCCH2SH、-(CH2)3OOC(CH2)2SH、-(CH2)8SH、-(CH2)6CH(SH)CH3、-(CH2)7SH、-CH2SH、-(CH2)2SH、-(CH2)5CH=CH(CH2)5SH、-(CH2)5CH=CH(CH2)3CH(SH)CH3、-(CH2)5CH(SH)(CH2)4CH=CH2、-(CH2)6CH(SH)(CH2)3CH=CH2、-(CH2)6CH(SH)(CH2)3CH(SH)CH3、-(CH2)5CH(SH)(CH2)4CH(SH)CH3、-(CH2)5CH(SH)(CH2)6SH、-(CH2)6CH(SH)(CH2)6SH、1-巯基-4-环十二-8-烯基、1-巯基-5-环十二-8-烯基、1,6-二巯基-10-环十二烷基、1-巯基-2-环丁基、1-巯基-3-环丁基、1-巯基-2-环戊基、1-巯基-3-环戊基、1-巯基-2-环己基、1-巯基-3-环己基、1-巯基-4-环己基、1-巯基-2-环庚基、1-巯基-3-环庚基、1-巯基-4-环庚基、1-巯基-2-环辛基、1-巯基-3-环辛基、1-巯基-4-环辛基、1-巯基-5-环辛基、1,2-二巯基-4-环己基、1-巯基环己-3-烯-3-基、1-巯基环己-3-烯-4-基、1-巯基环己-2-烯-4-基、-(CH2)3SCH2CH(SH)CH2SH、-(CH2)3S(CH2)3SH、-邻-(CH2)3OC6H4SH、-间-(CH2)3OC6H4SH、-对-(CH2)3OC6H4SH、-邻-(CH2)3OC6H4O(CH2)3SH、-间-(CH2)3OC6H4O(CH2)3SH、-对-(CH2)3OC6H4O(CH2)3SH、-邻-(CH2)3C6H4SH、-间-(CH2)3C6H4SH、-对-(CH2)3C6H4SH、-邻-C6H4SH、-间-C6H4SH、-对-C6H4SH、-(CH2)OOC(CH2)11SH和-(CH2)3OOC(CH2)9CH(SH)CH3。
基团RS优选是具有1至8个碳原子的直链或环状硫代烷基,特别优选具有3至6个碳原子的直链硫代烷基,尤其是-(CH2)3SH、-(CH2)6SH和-(CH2)4CH(SH)CH3。
通式(II)的基团Q是特别重要的,因为它们的结构允许特别快速的湿交联,这意味着可以优选地省去催化剂。
基团R3和R4优选是氢、可被非相邻氧原子中断的任选取代的脂族烃,也可以将基团R3和R4结合到环状结构或优选具有1至8个碳原子的任选取代的芳族烃中。
基团R3和R4的实例是烷基,诸如甲基、乙基、正丙基、异丙基、烯丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基或叔戊基、己基(诸如正己基)、庚基(诸如正庚基)、辛基(诸如正辛基、2,2,3,3-四甲基丁基或2-乙基-1-己基);环烷基,诸如环戊基或环己基;芳基,诸如苯基;烷芳基,诸如邻-、间-或对-甲苯基、二甲苯基;烷芳基,诸如苄基;取代的烷基,诸如2-甲氧基乙基、2-乙氧基乙基、2-异丙氧基乙基、3-甲氧基丙基、3-乙氧基丙基、3-异丙氧基丙基、3-丁氧基丙基或2-(N,N-二甲基氨基)乙基;取代的芳基,诸如4-甲氧基苯基;和杂芳族基团,诸如2-吡啶基、N-咪唑基或2-四氢呋喃基。
-NR4R3单元(其中R3和R4以环状结构形式存在)的实例是N-咪唑基、N-吡咯基、N-3-吡咯啉基、N-吡咯烷基、N-哌啶基、N-4-甲基哌嗪基、N-吡咯烷酮基或N-吗啉基。
NR4R3单元特别优选是二正丁基氨基、苯胺基、环己基氨基或N-吗啉代单元,非常特别优选是二正丁基氨基或环己基氨基单元。
基团R5和R6优选是氢。
本发明的有机(聚)硅氧烷(A)优选是由总共平均优选10至400,更优选10至200,尤其是10至100个通式(I)的单元组成的直链、链式聚硅氧烷。
基于通式(I)的所有单元,其中n=0的单元的比例优选不超过20摩尔%,尤其是不超过10摩尔%。
基于通式(I)的所有单元,其中n=1的单元的比例优选不超过20摩尔%,尤其是不超过10摩尔%。
优选地,通式(I)的所有单元的至少0.5摩尔%是通式(III)的单元。
基于通式(I)的所有硅氧烷单元,本发明的聚硅氧烷(A)中的烷氧基OR7的比例优选为1至40摩尔%,更优选2至15摩尔%之间,尤其是2至10摩尔%之间。
本发明的有机(聚)硅氧烷(A)优选含有至少1个脂族不饱和基团Ru和至少2个硫醇官能化基团RS。为了确保足够的交联密度,基于通式(I)的所有硅氧烷单元,可辐射交联基团Ru和RS的浓度在每种情况下优选在1-30摩尔%的范围内,更优选在3至20摩尔%之间,尤其在5至15摩尔%之间。基团RS与基团Ru的摩尔比优选在0.3至5之间,更优选0.4至4之间,尤其是0.5至3之间的范围内。
本发明的有机(聚)硅氧烷(A)可通过硅酮化学中已知的方法制备。优选通式(IV)的烷氧基硅烷
(R2O)3Si-CR5R6-NR4R3 (IV)
与聚硅氧烷(V)的硅烷醇基团的缩合,所述聚硅氧烷(V)含有脂族不饱和基团Ru和硫醇官能化基团RS。这种含硅烷醇的聚硅氧烷(V)的制备描述于例如DE4120418A1中。因为硫醇官能化基团RS优选经由相应的硫醇官能化烷氧基硅烷结合到聚硅氧烷骨架中,所以聚硅氧烷(V)由于其制备可能已经含有烷氧基,所述烷氧基在与通式(IV)的烷氧基硅烷的缩合反应中被优选地保留。
在优选的实施方案中,有机(聚)硅氧烷(A)具有源自聚硅氧烷(V)的末端单元(R2O)2R1SiO(1/2)。在有机(聚)硅氧烷(A)中,通式(III)的单元与式(R2O)2R1SiO(1/2)的末端单元的比率优选为20∶80至90∶10,更优选40∶60至80∶20。
通式(IV)的烷氧基硅烷的实例是
N,N-二甲基氨基甲基三乙氧基硅烷、N,N-二乙基氨基甲基三乙氧基硅烷、N,N-二异丙基氨基甲基三乙氧基硅烷、N,N-二乙基氨基甲基三异丁氧基硅烷、N,N-二异丙基氨基甲基三异丙氧基硅烷,、N-丁基氨基甲基三乙氧基硅烷、N,N-二丁基氨基甲基三乙氧基硅烷、N-环己基氨基甲基三乙氧基硅烷、N-环己基-N-甲基氨基甲基三乙氧基硅烷、N-吗啉代甲基三乙氧基硅烷、N-苯胺基甲基三甲氧基硅烷、N-吡咯烷基甲基三乙氧基硅烷、1-[(三乙氧基甲硅烷基)甲基]-1H-吡咯、1-[(三乙氧基甲硅烷基)甲基]-哌嗪、1-甲基-4-[(三乙氧基甲硅烷基)甲基]哌嗪、1-[(三乙氧基甲硅烷基)甲基]哌啶和1-[1-(三乙氧基甲硅烷基)乙基]-2-吡咯烷酮,特别优选N,N-二丁基氨基甲基三乙氧基硅烷、N-环己基氨基甲基三乙氧基硅烷和N-吗啉代甲基三乙氧基硅烷。还可以单独地或以与通式(IV)的硅烷的混合物的形式使用所提及的通式(IV)的硅烷的混合物和/或部分水解产物或混合的部分水解产物。
聚硅氧烷(V)与通式(IV)的烷氧基硅烷的反应优选在室温和大气压下进行。由于新形成的通式(III)的单元和通式(IV)的烷氧基硅烷二者与大气湿气的高反应性,该反应优选在排除湿气的情况下,例如在干燥的氮气气氛中进行。为了将存在于聚硅氧烷(V)中的硅烷醇基团尽可能完全地转化成通式(III)的单元,优选使用相对于硅烷醇基团化学计量过量的烷氧基硅烷(IV)。该过量优选为至少5摩尔%,更优选至少20摩尔%,特别是至少50摩尔%。过量的烷氧基硅烷可以在反应之后任选地在减压下蒸馏出。优选地,它保留在混合物中。为了使过量的烷氧基硅烷(IV)能够影响在湿固化期间形成的硫化产品的交联速率和模量,在缩合反应中从一开始就使用更高比例的烷氧基硅烷(IV)并且将过量的烷氧基硅烷(IV)留在可交联的有机(聚)硅氧烷混合物(M)中甚至有时可能是有利的。
当混合物的粘度非常高和/或通式(IV)的烷氧基硅烷为固体时,在反应中使用溶剂可能是有利的。优选使用不含OH基团的溶剂,以避免可改变反应性的烷氧基硅烷(IV)和有机(聚)硅氧烷(A)中的烷氧基的交换。当需要完全或部分替代烷氧基硅烷(IV)中存在的烷氧基时,例如为了降低反应性,可以使用具有醇OH基团的溶剂。然后必须根据需要相应地调节类型和摩尔比以及反应条件诸如时间、温度和压力。在反应期间或之后,优选将从通式(IV)的硅烷中释放的醇与任何过量的所添加的含醇OH基团的溶剂一起完全或部分蒸馏出。
溶剂的实例是烷烃例如戊烷、异戊烷、己烷、庚烷和异辛烷或其混合物,芳烃例如苯、甲苯、二甲苯和均三甲苯,卤代烃例如亚甲基氯、氯仿和1,2,3-三氯丙烷,羧酸酯例如乙酸丁酯和乙酸乙酯,醚例如二乙醚、四氢呋喃、2-甲基四氢呋喃、甲基叔丁基醚、苯甲醚和二丁基醚或不同溶剂的混合物。具有醇OH基团的溶剂的实例是乙醇、正丙醇、异丙醇、正丁醇、异丁醇、2-丁醇、正戊醇、丙烷-1,2-二醇、丙烷-1,3-二醇和甘油。
可以使不同聚硅氧烷(V)的混合物和通式(IV)的烷氧基硅烷的混合物彼此反应。聚硅氧烷(V)与多于一种烷氧基硅烷(IV)连续反应也是可能的。本发明的主要优点是对于聚硅氧烷(V)与烷氧基硅烷(IV)的缩合反应或对于湿交联不需要催化剂。两者均在室温下在几分钟至几小时内进行。
本发明还提供包含有机(聚)硅氧烷(A)的可湿交联和可辐射交联的有机(聚)硅氧烷混合物(M)。
高反应性意味着在本发明的有机(聚)硅氧烷(A)的存储期间和它们所存在于其中的混合物(M)中必须排除水分。
有机(聚)硅氧烷混合物(M)中的光交联是基于自由基反应。因此,有机(聚)硅氧烷混合物(M)优选包含光引发剂(B)。可用于本发明的光引发剂可选自任何已知的在辐射时形成自由基的类型。合适的光引发剂包括UV引发剂,诸如二苯甲酮和取代的二苯甲酮、苯乙酮和取代的苯乙酮,苯偶酰及其二烷基缩酮、苯偶姻及其烷基醚、二酰基氧化膦(尤其是二苯甲酰基氧化膦)、氧杂蒽酮和取代的氧杂蒽酮。典型的代表是苯乙酮、2-乙氧基-2-甲基苯乙酮、三氯丁基苯乙酮、2-乙氧基-2-苯基苯乙酮、异亚丙基丙酮、苯丙酮、二苯甲酮、氧杂蒽酮、二乙氧基苯乙酮(DEAP)、苯偶姻甲醚、苯偶姻乙醚、苯偶姻异丙醚、二乙氧基氧杂蒽酮、噻吨酮、3-氯氧杂蒽酮、氯噻吨酮、异丙基噻吨酮、芴酮、苯甲醛、芴、蒽醌、咔唑、N-乙烯基咔唑、3-甲基苯乙酮、4-甲基苯乙酮、3-溴苯乙酮、4-甲基二苯甲酮、4-氯二苯甲酮、4,4-二甲氧基二苯甲酮、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙-1-酮、偶氮二异丁腈、N-甲基二乙醇胺-二苯甲酮、苯偶酰二甲基缩酮、2-羟基-2-甲基苯丙酮(称为1173)、2-羟基-2-甲基苯丙酮、苯基双(2,4,6-三甲基苯甲酰基)氧化膦及其组合。
光引发剂的选择取决于层/应用的厚度、照射波长和期望的固化速率,并且还取决于与配制物的其它组分的可混溶性。对于低于350nm的UV波长,优选使用α-羟基酮类型的光引发剂。光引发剂以允许对于各自的要求最佳的固化条件的浓度使用。基于有机(聚)硅氧烷组合物(M)的总重量,优选的范围包括约0.05至约5重量%,更优选约0.1至约1重量%。
为了避免不希望的自由基反应,向本发明的有机(聚)硅氧烷混合物(M)中加入防止这种副反应的稳定剂(C),诸如氢醌、氢醌单甲醚(MEHQ)、4-叔丁基焦儿茶酚、4-硝基苯酚和丁基化羟基甲苯(BHT)。
有机(聚)硅氧烷混合物(M)还可包含填料(D),可以添加该填料(D)以优化未交联混合物的流变性质或硫化产品性质。此类填料的实例是沉淀或高度分散的二氧化硅诸如白垩、石英、有机填料,诸如淀粉、纤维素、微纤维素(如果合适)、竹纤维、聚乙烯纤维和聚丙烯腈粉末。也可以加入某些固体以改变电导率或热导率。实例是炭黑、石墨烯、碳纳米管、金属粉末(诸如铝、铁、银、铜或金粉末)、氢氧化铝、氧化铝、二氧化钛、铁氧化物、玻璃珠、硫酸钡、硫酸钠、硫酸镁、硫酸钙、碳酸钙、硅酸钙、磷灰石、钛酸钡、硅、碳化硅、氮化硅、氮化硼或碳化硼。也可以使用一种以上不同的填料。取决于用途,它们在有机(聚)硅氧烷混合物(M)中的比例在0至70%之间。
其它添加剂(E)是例如染料诸如荧光标记物,诸如Tinopal OB(BASF)、KB-140和KB-6002(Kustom Group),荧蒽,香豆素120,芘衍生物和二萘嵌苯。粘合促进剂(E),诸如粘合促进剂AMS 70、系列:GF31、GF62、GF91、GF92、GF93、GF95和GF96,或环氧官能化合物诸如Glymo、环氧官能聚硅氧烷或它们的部分水解产物也可以单独添加或以混合物的形式添加以改善有机(聚)硅氧烷混合物(M)的硫化产品对印刷电路板或金属基材的粘附性。
为了改变硫化产品的粘度和固化性能以及硬度,还可以向有机(聚)硅氧烷混合物(M)添加所谓的反应性稀释剂。这应当优选与有机(聚)硅氧烷混合物(M)的有机(聚)硅氧烷混溶,并且在交联过程期间以使得它变成通过本发明的混合物的交联形成的硫化产品的一部分的这样的方式反应。术语反应性稀释剂本身并不意味着添加该添加剂导致本发明的有机(聚)硅氧烷混合物(M)的粘度降低,而仅仅意味着基础成分有机(聚)硅氧烷(A)被稀释。这可能是出于经济原因或为了帮助改善性能特征。
反应性稀释剂的实例是硫醇官能化烷氧基硅烷,例如3-硫代丙基三甲氧基硅烷、3-硫代丙基甲基二甲氧基硅烷,或其部分水解产物或其与其他烷氧基硅烷(诸如甲基三甲氧基硅烷、正十六烷基三甲氧基硅烷或乙烯基三甲氧基硅烷)的共同部分水解产物,或硫醇官能化有机交联剂诸如季戊四醇四(3-巯基丙酸酯)、季戊四醇四(2-巯基乙酸酯)、季戊四醇四(3-巯基丁酸酯)或三羟甲基丙烷三(2-巯基乙酸酯),或通式(IV)的烷氧基硅烷或其部分水解产物或共水解产物,以及非官能烷氧基硅烷(例如四乙氧基硅烷、二甲基二甲氧基硅烷、甲基三乙氧基硅烷、甲基三甲氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、烯丙基三乙氧基硅烷、烯丙基三甲氧基硅烷、正十六烷基三甲氧基硅烷、正辛基三乙氧基硅烷、正辛基三甲氧基硅烷、2,2,3,3-四甲基丁基三甲氧基硅烷、2,2,3,3-四甲基丁基三乙氧基硅烷)或其水解产物或部分水解产物、硅树脂(优选具有可交联的烷氧基和任选的乙烯基和/或硫醇基),硅油(优选在与本发明的有机(聚)硅氧烷(A)(例如WO2018/162033A1中所述的)和DE102011081264 A1中所述的反应性有机聚合物的条件相当的条件下经受湿交联的那些)。可湿交联性还允许在阴影区域中交联并且防止未交联成分从硫化产品的不期望的后续迁移。为此,优选使用在与本发明的有机(聚)硅氧烷(A)的条件类似的条件下可湿交联的添加剂。此类反应性稀释剂以优选不超过50重量%,更优选不超过30重量%,尤其不超过10重量%的比例用于有机(聚)硅氧烷混合物(M)中。在添加的反应性稀释剂由于脂族不饱和基团和/或硫醇官能团的存在还可能参与辐射固化的情况下,相应的脂族不饱和基团应优选与硫醇官能团处于化学计量平衡。
溶剂也可用于降低粘度和/或改善有机(聚)硅氧烷混合物(M)的各组分的混溶性。为此可以考虑与以上针对聚硅氧烷(V)和通式(IV)的烷氧基硅烷的缩合的方法步骤所述的那些相同的溶剂。这些优选在施用之后但在固化之前大量蒸发。术语溶剂不意味着所有组分必须溶解在其中。优选地,溶剂以0%至50重量%,更优选0%至30重量%,尤其是0%的比例用于有机(聚)硅氧烷混合物(M)中。
为了制备有机(聚)硅氧烷混合物(M),相关混合物的所有成分可以以任何顺序彼此混合。混合优选在室温下进行。
如果有机(聚)硅氧烷混合物(M)由多于一种组分制备,则在包含通式(III)的硅氧烷单元的组分的情况下,应排除在水分存在下的储存;在含有RS和Ru基团的组分的情况下,储存应当避光保护。
当有机(聚)硅氧烷混合物(M)由单一组分组成时,应确保在排除水分和光线的情况下储存。
有机(聚)硅氧烷混合物(M)具有在25℃下优选1至100 000mPa·s,更优选30至5000mPa·s,尤其是30至1000mPa·s的粘度。
有机(聚)硅氧烷混合物(M)可用于在暴露于湿气时和/或通过辐射可交联的组合物迄今为止已经使用的所有目的,尤其是用于产生涂层。
本发明的混合物可以施用到到其上以产生涂层的基材的实例是电子印刷电路板、母板、陶瓷物体或玻璃(包括玻璃纤维,其转而包括光纤)、纸(诸如牛皮纸或玻璃纸)、纸板(包括由石棉制成的板)、玻璃纸、木材、软木、塑料薄膜(例如硅酮薄膜、聚乙烯薄膜或聚丙烯薄膜、PET薄膜)、由天然纤维或合成有机纤维或玻璃纤维制成的织造或非织造织物、金属(诸如铝箔)、聚乙烯涂布的牛皮纸或聚乙烯涂布的纸板。在以上提及聚乙烯的情况下,其在每种情况下可意指高压、中压或低压聚乙烯。
有机(聚)硅氧烷混合物(M)可以以任何适合和熟知的用于由液体物质产生涂层的方式,例如通过浸渍、刷涂、浇注、喷涂、辊涂、刮涂或刮板涂布施用到待涂布的基材。
有机(聚)硅氧烷混合物(M)非常适合于嵌入电气或电子元件。
可以使用有机(聚)硅氧烷混合物(M)而嵌入的电子元件的实例是混合电路,例如用于电子点火器、模块、光伏太阳能发电机和其他半导体阵列的混合电路。
优选地,有机(聚)硅氧烷混合物(M)在用于产生涂层或用于嵌入电气或电子元件时通过紫外光进行预交联,照射时间优选选择为以便在硫化产品上产生触摸干燥的表面。硫化产品的照射部分的后交联或阴影区域中的交联然后通过有机(聚)硅氧烷混合物(M)中存在的通式(III)的硅氧烷单元的湿交联,优选在空气中进行。有机(聚)硅氧烷混合物(M)中通式(III)的硅氧烷单元的比例越高并且相对湿度越高,该交联的速率越大。
有机(聚)硅氧烷混合物(M)的辐射固化优选通过在商业照射设备中在UV光的频率范围内照射来实现。在此,本领域技术人员可以容易地使照射条件诸如强度和持续时间适应环境和要求。实施例描述了导致快速皮膜形成直至在mm范围内的深度固化的典型条件。然而,它们不应被认为是限制性的。
在本发明的上下文中,根据ISO 2555在加热至23℃后使用来自A.Paar(Brookfield systems)的DV 3P旋转粘度计,使用转子5在2.5rpm下测定粘度。
所有粘度数据涉及23℃的温度,其在下文中也称为室温。
实施例:
实施例1(SH:Vi~2.5:1的聚硅氧烷(V)的制备)
向具有磁耦合的玻璃桨式搅拌器、滴液漏斗、温度计和带有柱头的回流冷凝器的0.5L法兰烧瓶装入18.7g的乙烯基甲基二氯硅烷(99%,Wacker Chemie AG),并且在25-27℃下,在20分钟的过程中计量加入152.2g的具有平均27个二甲基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG)。加入0.16g的3,5-二叔丁基-4-羟基甲苯(99%,Sigma-Aldrich)作为稳定剂,然后将混合物加热至100℃并在该温度下搅拌1小时。然后加入0.54g的“PNCl2”(Wacker Chemie AG,平衡催化剂)。在20分钟的时间内,将45g的3-硫代丙基甲基二甲氧基硅烷(≥95%,Sigma-Aldrich)计量加入透明的反应混合物中,然后加入另外0.54g的“PNCl2”。将混合物在100℃下再搅拌2小时,冷却至80℃,并加入30g的1%盐酸,之后将其搅拌15分钟,然后加入4g氧化镁在20g去离子水中的悬浮液。然后将反应混合物在80℃下搅拌1小时,之后在1hPa下将所有挥发物蒸馏出直至110℃。将残余物冷却至室温,然后通过压力吸滤器过滤。获得粘度为65mPa·s的透明液体作为滤液。
通过1H和29Si NMR测定产物的组成。这给出以下平均组成:
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.9:0.1:29.5:2:5.1
X=54% OH,46% OMe
在室温下在琥珀色玻璃瓶中储存6个月后,粘度仅增加至76mPa·s。
实施例1a(SH:Vi~2.5:1的聚硅氧烷(V)的制备)
重复实施例1,但使用33g的9%盐酸代替30g的1%盐酸。
以类似方式的后处理导致分离出粘度为1203mPa·s的油性液体,其根据NMR光谱具有以下平均组成:
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.8:0.2:116.6:6.6:16.4
X=95% OH,5% OMe
在室温下在琥珀色玻璃瓶中储存5周后,聚合物交联形成透明凝胶。较低的残留甲氧基含量不利于聚硅氧烷(V)的储存稳定性。
实施例2(SH:Vi~1:2的聚硅氧烷(V)的制备)
向具有磁耦合的玻璃桨式搅拌器、滴液漏斗、温度计和带有柱头的回流冷凝器的1L 4颈烧瓶装入18.7g的乙烯基甲基二氯硅烷(99%,Wacker Chemie AG),并且在24℃下,在10分钟的过程中计量加入47.7g的具有25摩尔%的甲基乙烯基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG)。然后在20分钟的过程中加入104.5g的具有平均27个二甲基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG)。加入0.16g的3,5-二叔丁基-4-羟基甲苯(99%,Sigma-Aldrich)作为稳定剂,然后将混合物加热至100℃并在该温度下搅拌1小时。然后加入0.5g的三氟甲磺酸(Merck)。在20分钟的时间内,将22.7g的3-硫代丙基甲基二甲氧基硅烷(≥95%,Sigma-Aldrich)计量加入到透明反应混合物中,然后加入另外0.5g的三氟甲磺酸。将混合物在100℃下再搅拌2小时,冷却至80℃,并加入4g氧化镁在46.6g去离子水中的悬浮液。然后将反应混合物在80℃下搅拌1小时,之后在1hPa下将所有挥发物蒸馏出直至110℃。
将残余物冷却至室温,然后通过压力吸滤器过滤。获得粘度为473mPa·s的透明液体作为滤液。通过1H和29Si NMR测定产物的组成。这给出以下平均组成:
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.6:0.4:48.2:6.7:4
X=67% OH,33% OMe
实施例3(SH:Vi~1:2的有机(聚)硅氧烷(A)的制备)
将来自实施例2的60g聚硅氧烷与18.6g的N,N-二正丁基氨基甲基三乙氧基硅烷在室温下在搅拌的同时混合。此后立即记录透明混合物的1H-和29Si-NMR光谱。由积分计算各甲硅烷氧基单元的摩尔比。对2个端基的归一化给出以下组成:
MeO-Me2SiO1/2:MeO-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2:(nBu)2N-CH2-Si(OEt)2O1/2:(nBu)2N-CH2-Si(OEt)3=0.5:0.2:46.3:6:3.7:1.3:3.4
据此,所有的SiOH基团已经与三烷氧基硅烷反应,而过量的硅烷和甲氧基端基不变地存在。
实施例4-交联测试
将10g的来自实施例3的产物与1g的四乙氧基部分水解产物(Wacker TES40)、4g的硅树脂(MQ树脂803)和0.2g的光引发剂1173(Sigma-Aldrich,2-甲基-1-苯基-丙-2-醇-1-酮)混合。将粘度为709mPa·s的透明混合物的一部分以约0.1mm的层厚度倾倒入玻璃槽中,并且在UV室(Uvacube,Hg halide lamp,290-415nm,2000W)中进行UV照射后,在15秒内交联成透明的硫化产品。
在没有照射的情况下,在约45分钟内在空气中在混合物的表面上形成干燥无粘性的皮膜,并且样品在几小时后完全交联。
实施例5(SH:Vi~1:2的有机(聚)硅氧烷(A)的制备)
向具有磁耦合的玻璃桨式搅拌器、滴液漏斗、温度计和带有柱头的回流冷凝器的0.5L 3颈烧瓶装入207.5g的具有平均420个二甲基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG),并加入94.6g的具有25摩尔%比例的甲基乙烯基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG)。然后在25分钟的过程中计量加入37.1g的乙烯基甲基二氯硅烷(99%,Wacker Chemie AG)。加入0.3g的3,5-二叔丁基-4-羟基甲苯(99%,Sigma-Aldrich),将混合物加热至100℃并在该温度下搅拌约25分钟。加入0.4g的10%“PNCl2”的甲苯溶液,然后将混合物在100℃下再搅拌2小时。
在30分钟的时间内,将45g的3-硫代丙基甲基二甲氧基硅烷(≥95%,Sigma-Aldrich)计量加入现在透明反应混合物中,然后加入另外0.4g的10%“PNCl2”溶液。将混合物在100℃下再搅拌2小时,冷却至80℃,并加入7.9g氧化镁在92.7g去离子水中的悬浮液。在80℃下再继续搅拌75分钟,然后使混合物冷却。静置时,反应混合物分离成油相和水相。通过在5000rpm下离心将固体从油相中分离,然后将透明液体在5hPa下加热至110℃。
分离出粘度为1500mPa·s的透明液体。通过1H和29Si NMR测定产物的组成。这给出以下平均组成:
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.58:0.42:45.3:6.2:3.7
X=53% OH,47% OMe
实施例6a(SH:Vi~1:2的有机(聚)硅氧烷(A)的制备)
将来自实施例5的20g聚硅氧烷与4.64g的N,N-二正丁基氨基甲基三乙氧基硅烷在室温下在搅拌的同时混合。
实施例6b(本发明的聚硅氧烷(A)(SH:Vi~1:2)的制备)
将来自实施例5的20g聚硅氧烷与4.4g的N-环己基氨基甲基三乙氧基硅烷在室温下在搅拌的同时混合。
实施例7-有机(聚)硅氧烷(A)的制备
7a)(SH:Vi~1:2的聚硅氧烷(V)的制备)和2*0.01重量%的PNCl2催化剂
向具有磁耦合的玻璃桨式搅拌器、滴液漏斗、温度计和带有柱头的回流冷凝器的2L法兰烧瓶装入56g的乙烯基甲基二氯硅烷(99%,Wacker Chemie AG),并且在25-27℃下,在每种情况下在半个小时的时间内,连续计量加入143g的具有25摩尔%比例的甲基乙烯基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG)和313.5g的具有平均27个二甲基甲硅烷氧基单元的α,ω-二羟基二甲基聚硅氧烷(Wacker Chemie AG)。加入0.5g的3,5-二叔丁基-4-羟基甲苯(99%,Sigma-Aldrich)作为稳定剂,然后将混合物加热至100℃并在该温度下搅拌1小时。然后加入0.6g的10%“PNCl2”的二甲苯溶液(WackerChemie AG,平衡催化剂)(基于总混合物,相当于0.01重量%)。在30分钟的时间内,将68g的3-硫代丙基甲基二甲氧基硅烷(≥95%,Sigma-Aldrich)计量加入透明反应混合物中,然后加入另外0.6g的10%“PNCl2”溶液。将混合物在100℃下再搅拌2小时,冷却至80℃,并加入12g氧化镁在140g去离子水中的悬浮液。然后将反应混合物在75℃-80℃下搅拌75分钟,之后在1hPa下将所有挥发物蒸馏出直至110℃。将残余物冷却至室温,然后通过压力吸滤器过滤。获得粘度为42mPa·s的透明液体作为滤液。通过1H和29Si NMR测定产物的组成。这给出以下平均组成:
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.74:0.26:21:3:1.7
X=39% OH,61% OMe
7b)用基于总混合物2*0.1重量%的“PNCl2”重复实施例7a)。
以类似方式的后处理导致分离出粘度为65mPa·s粘度的透明液体。通过1H和29SiNMR测定产物的组成。这给出以下平均组成:
X-Me2SiO1/2:X-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2=1.67:0.33:27:3.8:2
X=64% OH,36% OMe
7c)–有机(聚)硅氧烷(A)的制备
在室温下将60g的来自实施例7a)的聚合物(根据NMR分析:21mmol SiOH)与7.7g(25mmol)的N,N-二正丁基氨基甲基三乙氧基硅烷、11.2g(59mmol)的乙烯基三乙氧基硅烷(99%,Wacker Chemie AG)和作为稳定剂的0.3g的3,5-二叔丁基-4-羟基甲苯(99%,Sigma-Aldrich)的搅拌的同时混合。此后立即记录透明混合物的1H-和29Si-NMR光谱。由积分计算各甲硅烷氧基单元的摩尔比。对2个端基的归一化给出以下组成:
MeO-Me2SiO1/2:MeO-MeViSiO1/2:Me2SiO2/2:MeViSiO2/2:MeSi(CH2CH2CH2-SH)O2/2:(nBu)2N-CH2-Si(OEt)2O1/2:ViSi(OEt)2O1/2:(nBu)2N-CH2-Si(OEt)3:ViSi(OEt)3=1.1:0.1:27:3.3:1.7:0.6:0.2:0.2:2=>60% MeO,30% DBA-DEO,10% Vi-DEO。
据此,所有的SiOH基团已经与三烷氧基硅烷反应,而过量的硅烷和甲氧基端基不变地存在。
在空气(23℃/50%相对湿度)中,聚合物在几小时内交联以形成凝胶状硫化产品。在UV室(Uvacube,Hg halide lamp,290-415nm,2000W)中进行UV照射后,含有1重量%Darocur 1173的聚合物的混合物在15秒内交联成透明的硫化产品。
来自实施例6的聚合物的交联
将1重量%的2-甲基-1-苯基-丙-2-醇-1-酮(Darocur 1173)或1-羟基环己基苯基酮(Omnirad 184),或二苯甲酮(Omnirad BP Flakes)或2,2-二甲氧基-2-苯基苯乙酮(Omnirad BDK)(所有光引发剂可从北卡罗来纳州的IGM商购获得)添加到来自实施例6a或6b的硅氧烷中。使用刮片(来自Byk Inc.)将混合物,一种粘度<1000mPa.s的透明无色油,以0.1mm的层厚施用到聚酯薄膜。然后在空气存在下照射涂布的聚酯基材。无论光引发剂如何,在UV室(来自公司的Uvacube 2000,配备有1000mJ/cm2的汞金属卤化物(F灯)光源,波长范围为290nm至415nm)中进行紫外线照射30秒后,涂层完全硬化,从而形成干燥的表面。当另一个样品在空气(50%相对湿度,23℃)存在和排除光线的情况下以相同方式放置在模具中进行肖氏硬度测量时,在不到40分钟内出现皮膜形成。紧接在UV交联之后,硫化产品的肖氏OO硬度为50;在随后将硫化产品在23℃和50%相对湿度下储存一周之后,湿交联导致达到最大值65。
存储试验:
各自含有1重量%的Omnirad BDK或二苯甲酮的聚合物6a)和6b)的混合物在70℃下在密闭容器中避光储存2周后,显示出不变的UV交联行为和湿交联行为。
测试:
使用商业印刷电路板(3cm x 7cm FR-4)测试以上实施例。这些电路板基材是双面镀锡的原型。在涂布之前,施加50μl的熔剂(NC265LR)并在测试表面上干燥过夜。如上所述混合硅氧烷P2和P1,然后首先用UV光固化所施加的涂层,并将样品在大气湿度下储存4天以完全固化。完全固化的印刷电路板在热量和湿度(85℃/85% RH,两周内)方面进行了测试。还测试了热稳定性(150℃,2周内)和温度变化(1000小时-40℃/140℃)。在这些测试之后,根据ASTM 3359-09标准划格法(一种确定涂层在基材上的粘附性的可靠方法)评估粘附性。这是通过用解剖刀以网格图案切入完全固化的涂层下至基材表面来完成的。然后将标准胶带粘贴到硫化产品表面并撕下。然后基于ASTM 3359-09中描述的象形图,根据剩余的方格数对粘附性评级/定量。结果示于下表中。在利用上述实施例的原型板的测试中,甚至在不添加粘合促进剂的情况下也观察到优异的粘附性,硫化产品强度和粘附性的优异稳定性也是如此。结果示于表1中。
表1
1)标度范围为0B(不良粘附性)至5B(最佳粘附性,没有从基材任何地方的脱离)。
Claims (11)
1.由通式(I)的单元组成的有机(聚)硅氧烷(A)
RnSiO(4-n/2(I)
其中
n为0、1、2或3,其中n=0的单元的比例不大于50摩尔%,且n=1的单元的比例不大于60摩尔%,在每种情况下均基于通式(I)的所有单元,
R选自基团R1、–OR2、Ru、RS和Q,其中
R1表示具有1至18个碳原子的单价取代或未取代的烃基,
R2表示氢原子或具有1至6个碳原子的单价取代或未取代的烃基,
Ru表示具有2至18个碳原子的单价脂族不饱和烃基,
RS表示具有1至18个碳原子的单价硫醇官能化烃基,
Q是式(II)的氮官能团
-CR5R6-NR4R3(II),
其中
R3和R4各自独立地表示氢或具有1至18个碳原子的取代或未取代的烃基,并且
R5和R6各自独立地表示氢或甲基,
条件是所述有机(聚)硅氧烷(A)每分子含有至少一个通式(III)的单元;至少1个脂族不饱和基团Ru;和至少2个硫醇官能化基团RS;
Q-Si(OR7)2O1/2(III)
其中R7如针对R2所定义的。
2.根据权利要求1所述的有机(聚)硅氧烷(A),其中Ru是乙烯基或烯丙基。
3.根据前述权利要求中任一项所述的有机(聚)硅氧烷(A),其中基团RS表示具有3至6个碳原子的直链硫代烷基。
4.根据前述权利要求中任一项所述的有机(聚)硅氧烷(A),其中单元-NR4R3选自二正丁基氨基、苯胺基、环己基氨基和N-吗啉代单元。
5.根据前述权利要求中任一项所述的有机(聚)硅氧烷(A),其具有10至400个通式(I)的单元。
6.根据前述权利要求中任一项所述的有机(聚)硅氧烷(A),其中通式(I)的所有单元的至少0.5摩尔%是通式(III)的单元。
7.根据前述权利要求中任一项所述的有机(聚)硅氧烷(A),其中所述基团RS与所述基团Ru的摩尔比在0.3至5之间的范围内。
8.制备有机(聚)硅氧烷(A)的方法,其中使通式(IV)的烷氧基硅烷
(R2O)3Si-CR5R6-NR4R3(IV)
与聚硅氧烷(V)的硅烷醇基团进行缩合,所述聚硅氧烷(V)含有硅烷醇基团以及脂族不饱和基团Ru和硫醇官能化基团RS。
9.可湿交联和可辐射交联的有机(聚)硅氧烷混合物(M),其包含根据权利要求1至7所述的有机(聚)硅氧烷(A)。
10.根据权利要求9所述的有机(聚)硅氧烷混合物(M),其包含光引发剂(B)。
11.根据权利要求9或10所述的有机(聚)硅氧烷混合物(M),其包含稳定剂(C)以避免不希望的自由基反应。
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