耐辐照硅橡胶研究
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摘要
本文系统地研究了提高硅橡胶(包括高温硫化硅橡胶和室温硫化硅橡胶)耐辐照性能的途径，合成了一系列能提高硅橡胶耐辐照性能的化合物作抗辐射剂，并利用IR、~1HNMR等对其进行了表征；研究了不同配方的硅橡胶样品在不同氛围(真空、氮气、空气)、不同辐照剂量下交联密度和力学性能的变化；同时，合成了具有优异的耐辐照性能的高苯基含量甲基苯基硅橡胶。
芳香族化合物(联苯、萘、菲)能有效地提高高温硫化硅橡胶的耐辐照性能，其辐射保护效果随着芳香性的增大而增大；菲由于在三者之中具有最大的芳香性而具有最好的辐射保护效果。当芳香族化合物的共轭原子数较多时，分子量较大，其熔点较高(高于硅橡胶的一段硫化温度170℃)，导致在硅橡胶体系中的分散性较差，进而影响了硅橡胶的综合力学性能和其辐射保护效果。因此，对联三苯和9，10二苯基蒽虽然含有较多的共轭原子，其对硅橡胶的辐射保护效果并不及上述三者。二苯乙炔和二苯甲酮由于其独特的辐射保护机理而具有很好的辐射保护效果。这些化合物在硅橡胶中的最佳用量为6份(重量份数)。由于芳香族化合物是物理性分散在硅橡胶体系内的，其辐射保护效果为“外保护”。
利用芳香族化合物来提高硅橡胶耐辐照性时，存在其在硅橡胶体系内的分散性和相容性的问题，因此通过化学反应把具有大共轭结构的多苯基基团引入到有机硅化合物中是一个很好的解决办法。利用四苯基环戊二烯酮和乙烯基的Diels—Alder反应合成了两种含有四苯基苯基的有机硅化合物：(四苯基苯基)三乙烯基四甲基环四硅氧烷和四甲基乙烯基(四苯基苯基)二硅氧烷。当前者作为添加剂应用于高温硫化硅橡胶时，由于其每分子内含有三个乙烯基，在辐照过程中过多的乙烯基非常容易引发辐射交联反应，因而其不能用作硅橡胶的耐辐照添加剂；而四甲基乙烯基(四苯基苯基)二硅氧烷则可以用作高温硫化硅橡胶的一种耐辐射添加剂，其最佳用量为4～6份。
因此，为了得到具有较好辐射保护效果的化合物，所合成的化合物理应具有如下条件：
(1)、含有较多的具有大共轭结构的稠环基团；
(2)、具有较低的熔点，最好在常温下为液态，且与硅橡胶的相容性较好；
(3)、体系内的乙烯基含量较少。
根据此原则，利用四苯基环戊二烯酮、苊式环戊二烯酮和菲式环戊二烯酮与C胶上的乙烯基进行Diels—Alder反应，分别合成了三种含稠环基团的乙烯基硅油：四苯基苯基乙烯基硅油(C_1胶)，苊式多苯基苯基乙烯基硅油(C_2胶)和菲式多苯基苯基乙烯基硅油(C_3胶)，并根据~1HNMR谱图上不同氢原子的积分面积计算了三种胶中稠环基团和乙烯基的含量。
把C_1胶、C_2胶或C_3胶作为一种耐辐射添加剂引入到高温硫化硅橡胶体系时，当采用过氧化物(双—2，5)硫化时，由于C_1胶、C_2胶或C_3胶侧链上的稠环基团具有大共轭结构，能够稳定橡胶硫化过程中过氧化物分解产生的自由基，进而随着含稠环基团的硅油用量的增多，硅橡胶变得不易硫化，即使增加过氧化物的用量，也不能很好地解决橡胶片“欠硫化”的问题；当利用氯铂酸作催化剂，采用加成型硫化体系时，含有C_1胶、C_2胶或C_3胶的硅橡胶样品都可以完全硫化，其最佳用量为10～14份。当C_1胶、C_2胶和C_3胶应用于二甲基二苯基硅橡胶时，由于硅橡胶体系中同时存在大量的苯基和稠环基团，二者会产生协同效应，所得样品具有较好的耐辐照性能。如在N_2中辐照后，甲基乙烯基硅橡胶的拉伸强度为5.7MPa(350kGy)，3.2MPa(500kGy)和2.0MPa(850kGy)；含有10份C_1胶的甲基乙烯基硅橡胶辐照后的拉伸强度分别为6.7MPa，4.5MPa和2.6MPa；含有10份C_1胶的二甲基二苯基硅橡胶的拉伸强度分别为8.7MPa，5.7MPa和3.5MPa。
C_1胶、C_2胶和C_3胶能明显地提高硅橡胶的耐辐照性能，主要归因于乙烯基硅油侧链上稠环基团的大共轭结构。稠环基团体系内的离域的大π键能够分散辐照时体系所吸收的辐射能，使激发能在分子间或分子内进行转移，从而避免了化学键的断裂，因而材料的耐辐照性能得到大幅度地提高。另外，当把含稠环基团的乙烯基硅油作为一种抗辐射剂来引入到硅橡胶体系中时，硅油分子链上少量的乙烯基则是必不可少的官能团。当硅橡胶在硫化时，C_1胶、C_2胶或C_3胶侧链上的乙烯基能参与交联反应而形成交联网络。在这个过程中，稠环基团就会被引入到交联网络中，其辐射保护效果可以称为“内保护”。
试验发现C_2胶具有最好的辐射保护效果。利用紫外光谱研究发现C_2胶侧链上的苊式多苯基苯基具有最大的芳香性。但是，在C_1胶、C_2胶和C_3胶三者中，C_1胶侧链上的四苯基苯基和C_3胶侧链上的菲式多苯基苯基都含有30个碳原子，而C_2胶侧链上的苊式多苯基苯基含有28个碳原子，比前面二者小2个碳原子，理应其芳香性在三者之中最小，但事实却恰恰相反。为了解释其原因，我们利用量子力学方法进行了计算，研究了三种稠环基团在B3LYP／6-31G*基组水平下优化得到的几何结构，发现苊式多苯基苯基中的萘环和中间的苯环共面，电子离域性最大，而其他二者所有苯环都不共面，发生了明显地扭曲；同时，在优化几何结构的基础上，对三种化合物进行了前线分子轨道的分析，利用密度泛函理论方法(density function theory，DFT)计算了稠环基团的最高占有轨道(HOMO)和最低未占轨道(LUMO)之间的能量差，即能隙(Eg)，发现C_2胶上苊式多苯基苯基的Eg最小，解释了C_2胶具有最好的辐射保护效果的原因。
利用甲基三氯硅烷和溴苯的格氏反应合成了甲基苯基二氯硅烷，用核磁分析证实了格氏反应中高沸点副产物为甲基二苯基氯硅烷；通过甲基苯基二氯硅烷和二甲基二氯硅烷的共水解，再裂解而制得含Me_2SiO链节的甲基苯基环硅氧烷混合物，进而利用碱胶开环聚合得到甲基苯基硅橡胶生胶；也可通过甲基苯基二氯硅烷水解所得甲基苯基环硅氧烷(D_3~(3Ph)、D_4~(4Ph_)与D_4开环聚合制得甲基苯基硅橡胶生胶。研究发现高苯基含量的甲基苯基硅橡胶(苯基含量30mol％)具有优异的耐辐照性能，这归因于体系内存在大量的具有共轭结构的苯基基团。如在经过450kGy的辐照后，其拉伸强度从6.0MPa降到5.4MPa，只降低10.0％。同时对比了甲基苯基硅橡胶和二甲基二苯基硅橡胶耐辐照性能的好坏。发现，当二者具有相同的苯基含量时，在经过高剂量的高能射线辐照后(900kGy)，甲基苯基硅橡胶的耐辐照性能稍微比二甲基二苯基硅橡胶要好。这应归因于前者体系内的苯基分布比后者较为均匀。
为了提高缩合型室温硫化硅橡胶的耐辐照性能，首次合成了两种新型的缩合型室温硫化硅橡胶交联剂：(苊式多苯基苯基)三乙氧基硅烷和(菲式多苯基苯基)三乙氧基硅烷。其熔点分别为：49℃和76℃，并通过核磁、红外谱图进行了表征。当(苊式多苯基苯基)三乙氧基硅烷和(菲式多苯基苯基)三乙氧基硅烷用作缩合型RTV硅橡胶的交联剂时，由于二者所含的稠环基团的空间位阻较大，因而样品硫化速度较慢。为了加快RTV胶的硫化速度，可提高温度促进样品的硫化(50～60℃)。研究发现，交联剂(苊式多苯基苯基)三乙氧基硅烷和(菲式多苯基苯基)三乙氧基硅烷能够有效地提高硅橡胶的耐辐照性能，其最佳用量为14～18份。
In this paper, ways to improve the radiation resistance of silicone rubber (including HTV and RTV silicone rubber) are studied systematically. And a series of compounds, characterized by IR and HNMR analysis, are synthesized and used as anti-rays to improve silicone rubber's radiation resistance. The changes of crosslinking density and mechanical properties under different atmosphere (in vacuum, N_2 and air) and different radiation dose are studied. Moreover, polymethylphenylsilicone rubber with excellent radiation resistance is also synthesized.
Aromatic compounds (such as biphenyl,.naphthalene and phenanthrene) can be used as additives to improve HTV silicone rubber's radiation resistance. The bigger the aromaticity, the better the radiation protection effects are. Phenanthrene has the best radiation protection effects among them. When the aromatic compounds contain more conjugated atoms, their molecular weight becomes bigger and their melting points become higher. Once the melting points are higher than 170℃(the first cure temperature of silicone rubber), their dispersion in rubber system becomes worse, which affects silicone rubber's mechanical properties and the radiation protection effects of aromatic additives. Thus the radiation protection effects of p-terphenyl and 9,10-diphenylanthracene are worse than biphenyl, naphthalene and phenanthrene in spite of their bigger conjugated structure. Diphenylacetylene and benzophenone have good radiation protection effects due to their special radiation protection mechanism. And the suitable amount of aromatic compounds used in silicone rubber is 6 phr (weight parts). Since aromatic compounds are dispersed physically in rubber system, their radiation protection effects can be characterized as "external protection".
When aromatic compounds are used to improve silicone rubber's radiation resistance, there exist two problems: their dispersion and compatibility in the rubber system. Introducing multi-phenylphenyl groups into silicone compound seems to be a good way to solve the problems. By the Diels-Alder reaction between tetraphenylcyclopentadienone and vinyl groups, two compounds containing tetraphenylphenyl groups are synthesized: (tetraphenylphenyl) trivinyltetramethyl cyclotetrasiloxane and tetramethylvinyl (tetraphenylphenyl) disiloxane. When the former is used in HTV silicone rubber, many vinyl groups are also introduced into rubber system, which can be easily broken by irradiation and then induce radiation crosslinking reactions. So, (tetraphenylphenyl) trivinyltetramethyl cyclotetrasiloxane can not be used to improve rubber's radiation resistance. While tetramethylvinyl (tetraphenylphenyl) disiloxane can be used to improve rubber's radiation resistance, and its suitable amount used is 4-6 phr.
Therefore, in order to obtain compounds with good radiation protection effects, the compounds should:
(1) Contain condensed aromatics with big conjugated structure;
(2) Have lower melting point and have good compatibility with silicone rubber,
(3) Contain less vinyl groups.
So, by the Diels-Alder reaction of tetraphenylcyclopentadienone, acenaphthenecyclone and benzophenanthrenecyclone with the vinyl groups in C gum, three kinds of polymethylvinylsilicone oil with condensed aromatics are synthesized respectively: polymethylvinylsilicone oil with tetraphenylphenyl groups (called C_1 gum for short), polymethylvinylsilicone oil with acenaphthenyl groups (C_2 gum) and polymethylvinylsilicone oil with benzophenanthrene groups (C3 gum). And the content of vinyl groups and condensed aromatics in C_1 gum, C_2 gum and C_3 gum is calculated by ~1HNMR analysis according to the integral value of various H atoms.
C_1 gum, C_2 gum and C_3 gum are used as additives in silicone rubber to improve the radiation resistance. When vulcanizates are cured by peroxide (DBPMH), the condensed aromatics with big conjugated structure have stabilization on radicals forming during decomposition of initiator and inhibit the crosslinking reactions of silicone rubber, causing the vulcanizates to be in a state of "lack of cure". Even increasing the amount of peroxide used, vulcanizates with better vulcanization characteristics are not easy to be obtained. When vulcanizates are cured by hydrosilylation, which is catalysed by chloroplatinic acid catalyst, vulcanizates can be cured adequately when C_1 gum, C_2 gum and C_3 gum are used. And their suitable amount used is 10-14 phr. When C_1 gum, C_2 gum and C3 gum are used in poly(dimethyl-diphenyl) silicone rubber, both the condensed aromatics and phenyl groups can provide radiation protection effects to silicone rubber with Synergistic effect. For example, after irradiated in N_2, the tensile strength of polymethylvinyl silicone rubber is 5.7 MPa (350 kGy), 3.2 MPa (500 kGy) and 2.0 MPa (850 kGy); the tensile strength of polymethylvinyl silicone rubber containing 10 phr C_1 gum is 6.7 MPa, 4.5 MPa and 2.6 MPa respectively; the tensile strength of poly(dimethyl-diphenyl) silicone rubber containing 10 phr C_1 gum is 8.7 MPa, 5.7 MPa and 3.5 MPa respectively.
The reason that C_1 gum, C_2 gum and C_3 gum can obviously improve silicone rubber's radiation resistance is attributed to the condensed aromatics in polymethylvinyl silicone oil. When samples are irradiated, the absorbed energy could dissipate in the large conjugated structure of condensed aromatics before bond rupture occurs. So the radiation resistance is improved greatly. In addition, the vinyl groups in silicone oil are necessary. During the curing of silicone rubber, condensed aromatics could be introduced into the molecular network of silicone rubber by the reaction of vinyl groups in C_1 gum, C_2 gum and C_3 gum. So, their radiation protection effects could be characterized as "internal protection".
According to the experiment results, C_2 gum has the best radiation protection effects among three gums. From the UV spectra, it can be found that the aromaticity of acenaphthenyl groups in C_2 gum is the largest. But there are 30 carbon atoms in the conjugated structure of condensed aromatics in C_1 gum and C_3 gum, while 28 carbon atoms in acenaphthenyl groups in C_2 gum. So, the aromaticity of acenaphthenyl groups in C_2 gum should be the least. In order to explain the reason, quantum chemical calculation is utilized. The optimized geometrical structrures of condensed aromatics in C_1 gum, C_2 gum and C_3 gum are calculated at B3LYP/6-31G* levels. We find that some phenyl groups in acenaphthenyl groups are coplanar and have the largest conjugated structure. While all the phenyl groups in tetraphenylphenyl groups or benzophenanthrene groups are not coplanar. At the same time, by density function theory (DFT), the electronic energy gap (Eg) between HOMO and LUMO frontier molecular orbitals of condensed aromatics are calculated and the Eg of acenaphthenyl groups in C_2 gum is the smallest, which explains the reason why C_2 gum has the best radiation protection effects.
Methylphenyldichlorosilane is synthesized by Grignard reaction between methyltrichlorosiliane with bromobenzene. And the by-product with high boiling point in Grignard reaction is proved as methyldiphenylchlorosilane by ~1HNMR analysis. By the hydrolyzation of MePhSiCl_2 and Me_2SiCl_2, polymethylphenylsilicone rubber can be obtained. And the rubber containing 30 mol% phenyl groups has excellent radiation resistance, which is attributed to the phenyl groups in rubber system. For example, after 450 kGy radiation, the tensile strength decreased from 6.0 MPa to 5.4 MPa, only decreased 10%. When the content of phenyl groups in rubber system is the same, the radiation resistance of polymethylphenylsilicone rubber is a little better than that of poly(dimethyl-diphenyl)silicone rubber after higher dose radiation (900 kGy). This is attributed to the distribution of phenyl groups in rubber system.
In order to improve the radiation resistance of condensed-type RTV silicone rubber, two kinds of crosslinking agents are synthesized successfully: triethoxysilane with acenaphthenyl groups (m.p. 49℃) and triethoxysilane with benzophenanthrene groups (m.p. 76℃), characterized by IR and ~1HNMR analysis. When they are used as crosslinking agent in condensed-type RTV silicone rubber, the curing speed can be accelerated by improving the curing temperature (50-60℃). After radiation, the results show that they can effectively improve the radiation resistance of RTV silicone rubber and their suitable amount used is 14-18 phr.
芳香族化合物(联苯、萘、菲)能有效地提高高温硫化硅橡胶的耐辐照性能，其辐射保护效果随着芳香性的增大而增大；菲由于在三者之中具有最大的芳香性而具有最好的辐射保护效果。当芳香族化合物的共轭原子数较多时，分子量较大，其熔点较高(高于硅橡胶的一段硫化温度170℃)，导致在硅橡胶体系中的分散性较差，进而影响了硅橡胶的综合力学性能和其辐射保护效果。因此，对联三苯和9，10二苯基蒽虽然含有较多的共轭原子，其对硅橡胶的辐射保护效果并不及上述三者。二苯乙炔和二苯甲酮由于其独特的辐射保护机理而具有很好的辐射保护效果。这些化合物在硅橡胶中的最佳用量为6份(重量份数)。由于芳香族化合物是物理性分散在硅橡胶体系内的，其辐射保护效果为“外保护”。
利用芳香族化合物来提高硅橡胶耐辐照性时，存在其在硅橡胶体系内的分散性和相容性的问题，因此通过化学反应把具有大共轭结构的多苯基基团引入到有机硅化合物中是一个很好的解决办法。利用四苯基环戊二烯酮和乙烯基的Diels—Alder反应合成了两种含有四苯基苯基的有机硅化合物：(四苯基苯基)三乙烯基四甲基环四硅氧烷和四甲基乙烯基(四苯基苯基)二硅氧烷。当前者作为添加剂应用于高温硫化硅橡胶时，由于其每分子内含有三个乙烯基，在辐照过程中过多的乙烯基非常容易引发辐射交联反应，因而其不能用作硅橡胶的耐辐照添加剂；而四甲基乙烯基(四苯基苯基)二硅氧烷则可以用作高温硫化硅橡胶的一种耐辐射添加剂，其最佳用量为4～6份。
因此，为了得到具有较好辐射保护效果的化合物，所合成的化合物理应具有如下条件：
(1)、含有较多的具有大共轭结构的稠环基团；
(2)、具有较低的熔点，最好在常温下为液态，且与硅橡胶的相容性较好；
(3)、体系内的乙烯基含量较少。
根据此原则，利用四苯基环戊二烯酮、苊式环戊二烯酮和菲式环戊二烯酮与C胶上的乙烯基进行Diels—Alder反应，分别合成了三种含稠环基团的乙烯基硅油：四苯基苯基乙烯基硅油(C_1胶)，苊式多苯基苯基乙烯基硅油(C_2胶)和菲式多苯基苯基乙烯基硅油(C_3胶)，并根据~1HNMR谱图上不同氢原子的积分面积计算了三种胶中稠环基团和乙烯基的含量。
把C_1胶、C_2胶或C_3胶作为一种耐辐射添加剂引入到高温硫化硅橡胶体系时，当采用过氧化物(双—2，5)硫化时，由于C_1胶、C_2胶或C_3胶侧链上的稠环基团具有大共轭结构，能够稳定橡胶硫化过程中过氧化物分解产生的自由基，进而随着含稠环基团的硅油用量的增多，硅橡胶变得不易硫化，即使增加过氧化物的用量，也不能很好地解决橡胶片“欠硫化”的问题；当利用氯铂酸作催化剂，采用加成型硫化体系时，含有C_1胶、C_2胶或C_3胶的硅橡胶样品都可以完全硫化，其最佳用量为10～14份。当C_1胶、C_2胶和C_3胶应用于二甲基二苯基硅橡胶时，由于硅橡胶体系中同时存在大量的苯基和稠环基团，二者会产生协同效应，所得样品具有较好的耐辐照性能。如在N_2中辐照后，甲基乙烯基硅橡胶的拉伸强度为5.7MPa(350kGy)，3.2MPa(500kGy)和2.0MPa(850kGy)；含有10份C_1胶的甲基乙烯基硅橡胶辐照后的拉伸强度分别为6.7MPa，4.5MPa和2.6MPa；含有10份C_1胶的二甲基二苯基硅橡胶的拉伸强度分别为8.7MPa，5.7MPa和3.5MPa。
C_1胶、C_2胶和C_3胶能明显地提高硅橡胶的耐辐照性能，主要归因于乙烯基硅油侧链上稠环基团的大共轭结构。稠环基团体系内的离域的大π键能够分散辐照时体系所吸收的辐射能，使激发能在分子间或分子内进行转移，从而避免了化学键的断裂，因而材料的耐辐照性能得到大幅度地提高。另外，当把含稠环基团的乙烯基硅油作为一种抗辐射剂来引入到硅橡胶体系中时，硅油分子链上少量的乙烯基则是必不可少的官能团。当硅橡胶在硫化时，C_1胶、C_2胶或C_3胶侧链上的乙烯基能参与交联反应而形成交联网络。在这个过程中，稠环基团就会被引入到交联网络中，其辐射保护效果可以称为“内保护”。
试验发现C_2胶具有最好的辐射保护效果。利用紫外光谱研究发现C_2胶侧链上的苊式多苯基苯基具有最大的芳香性。但是，在C_1胶、C_2胶和C_3胶三者中，C_1胶侧链上的四苯基苯基和C_3胶侧链上的菲式多苯基苯基都含有30个碳原子，而C_2胶侧链上的苊式多苯基苯基含有28个碳原子，比前面二者小2个碳原子，理应其芳香性在三者之中最小，但事实却恰恰相反。为了解释其原因，我们利用量子力学方法进行了计算，研究了三种稠环基团在B3LYP／6-31G*基组水平下优化得到的几何结构，发现苊式多苯基苯基中的萘环和中间的苯环共面，电子离域性最大，而其他二者所有苯环都不共面，发生了明显地扭曲；同时，在优化几何结构的基础上，对三种化合物进行了前线分子轨道的分析，利用密度泛函理论方法(density function theory，DFT)计算了稠环基团的最高占有轨道(HOMO)和最低未占轨道(LUMO)之间的能量差，即能隙(Eg)，发现C_2胶上苊式多苯基苯基的Eg最小，解释了C_2胶具有最好的辐射保护效果的原因。
利用甲基三氯硅烷和溴苯的格氏反应合成了甲基苯基二氯硅烷，用核磁分析证实了格氏反应中高沸点副产物为甲基二苯基氯硅烷；通过甲基苯基二氯硅烷和二甲基二氯硅烷的共水解，再裂解而制得含Me_2SiO链节的甲基苯基环硅氧烷混合物，进而利用碱胶开环聚合得到甲基苯基硅橡胶生胶；也可通过甲基苯基二氯硅烷水解所得甲基苯基环硅氧烷(D_3~(3Ph)、D_4~(4Ph_)与D_4开环聚合制得甲基苯基硅橡胶生胶。研究发现高苯基含量的甲基苯基硅橡胶(苯基含量30mol％)具有优异的耐辐照性能，这归因于体系内存在大量的具有共轭结构的苯基基团。如在经过450kGy的辐照后，其拉伸强度从6.0MPa降到5.4MPa，只降低10.0％。同时对比了甲基苯基硅橡胶和二甲基二苯基硅橡胶耐辐照性能的好坏。发现，当二者具有相同的苯基含量时，在经过高剂量的高能射线辐照后(900kGy)，甲基苯基硅橡胶的耐辐照性能稍微比二甲基二苯基硅橡胶要好。这应归因于前者体系内的苯基分布比后者较为均匀。
为了提高缩合型室温硫化硅橡胶的耐辐照性能，首次合成了两种新型的缩合型室温硫化硅橡胶交联剂：(苊式多苯基苯基)三乙氧基硅烷和(菲式多苯基苯基)三乙氧基硅烷。其熔点分别为：49℃和76℃，并通过核磁、红外谱图进行了表征。当(苊式多苯基苯基)三乙氧基硅烷和(菲式多苯基苯基)三乙氧基硅烷用作缩合型RTV硅橡胶的交联剂时，由于二者所含的稠环基团的空间位阻较大，因而样品硫化速度较慢。为了加快RTV胶的硫化速度，可提高温度促进样品的硫化(50～60℃)。研究发现，交联剂(苊式多苯基苯基)三乙氧基硅烷和(菲式多苯基苯基)三乙氧基硅烷能够有效地提高硅橡胶的耐辐照性能，其最佳用量为14～18份。
In this paper, ways to improve the radiation resistance of silicone rubber (including HTV and RTV silicone rubber) are studied systematically. And a series of compounds, characterized by IR and HNMR analysis, are synthesized and used as anti-rays to improve silicone rubber's radiation resistance. The changes of crosslinking density and mechanical properties under different atmosphere (in vacuum, N_2 and air) and different radiation dose are studied. Moreover, polymethylphenylsilicone rubber with excellent radiation resistance is also synthesized.
Aromatic compounds (such as biphenyl,.naphthalene and phenanthrene) can be used as additives to improve HTV silicone rubber's radiation resistance. The bigger the aromaticity, the better the radiation protection effects are. Phenanthrene has the best radiation protection effects among them. When the aromatic compounds contain more conjugated atoms, their molecular weight becomes bigger and their melting points become higher. Once the melting points are higher than 170℃(the first cure temperature of silicone rubber), their dispersion in rubber system becomes worse, which affects silicone rubber's mechanical properties and the radiation protection effects of aromatic additives. Thus the radiation protection effects of p-terphenyl and 9,10-diphenylanthracene are worse than biphenyl, naphthalene and phenanthrene in spite of their bigger conjugated structure. Diphenylacetylene and benzophenone have good radiation protection effects due to their special radiation protection mechanism. And the suitable amount of aromatic compounds used in silicone rubber is 6 phr (weight parts). Since aromatic compounds are dispersed physically in rubber system, their radiation protection effects can be characterized as "external protection".
When aromatic compounds are used to improve silicone rubber's radiation resistance, there exist two problems: their dispersion and compatibility in the rubber system. Introducing multi-phenylphenyl groups into silicone compound seems to be a good way to solve the problems. By the Diels-Alder reaction between tetraphenylcyclopentadienone and vinyl groups, two compounds containing tetraphenylphenyl groups are synthesized: (tetraphenylphenyl) trivinyltetramethyl cyclotetrasiloxane and tetramethylvinyl (tetraphenylphenyl) disiloxane. When the former is used in HTV silicone rubber, many vinyl groups are also introduced into rubber system, which can be easily broken by irradiation and then induce radiation crosslinking reactions. So, (tetraphenylphenyl) trivinyltetramethyl cyclotetrasiloxane can not be used to improve rubber's radiation resistance. While tetramethylvinyl (tetraphenylphenyl) disiloxane can be used to improve rubber's radiation resistance, and its suitable amount used is 4-6 phr.
Therefore, in order to obtain compounds with good radiation protection effects, the compounds should:
(1) Contain condensed aromatics with big conjugated structure;
(2) Have lower melting point and have good compatibility with silicone rubber,
(3) Contain less vinyl groups.
So, by the Diels-Alder reaction of tetraphenylcyclopentadienone, acenaphthenecyclone and benzophenanthrenecyclone with the vinyl groups in C gum, three kinds of polymethylvinylsilicone oil with condensed aromatics are synthesized respectively: polymethylvinylsilicone oil with tetraphenylphenyl groups (called C_1 gum for short), polymethylvinylsilicone oil with acenaphthenyl groups (C_2 gum) and polymethylvinylsilicone oil with benzophenanthrene groups (C3 gum). And the content of vinyl groups and condensed aromatics in C_1 gum, C_2 gum and C_3 gum is calculated by ~1HNMR analysis according to the integral value of various H atoms.
C_1 gum, C_2 gum and C_3 gum are used as additives in silicone rubber to improve the radiation resistance. When vulcanizates are cured by peroxide (DBPMH), the condensed aromatics with big conjugated structure have stabilization on radicals forming during decomposition of initiator and inhibit the crosslinking reactions of silicone rubber, causing the vulcanizates to be in a state of "lack of cure". Even increasing the amount of peroxide used, vulcanizates with better vulcanization characteristics are not easy to be obtained. When vulcanizates are cured by hydrosilylation, which is catalysed by chloroplatinic acid catalyst, vulcanizates can be cured adequately when C_1 gum, C_2 gum and C_3 gum are used. And their suitable amount used is 10-14 phr. When C_1 gum, C_2 gum and C3 gum are used in poly(dimethyl-diphenyl) silicone rubber, both the condensed aromatics and phenyl groups can provide radiation protection effects to silicone rubber with Synergistic effect. For example, after irradiated in N_2, the tensile strength of polymethylvinyl silicone rubber is 5.7 MPa (350 kGy), 3.2 MPa (500 kGy) and 2.0 MPa (850 kGy); the tensile strength of polymethylvinyl silicone rubber containing 10 phr C_1 gum is 6.7 MPa, 4.5 MPa and 2.6 MPa respectively; the tensile strength of poly(dimethyl-diphenyl) silicone rubber containing 10 phr C_1 gum is 8.7 MPa, 5.7 MPa and 3.5 MPa respectively.
The reason that C_1 gum, C_2 gum and C_3 gum can obviously improve silicone rubber's radiation resistance is attributed to the condensed aromatics in polymethylvinyl silicone oil. When samples are irradiated, the absorbed energy could dissipate in the large conjugated structure of condensed aromatics before bond rupture occurs. So the radiation resistance is improved greatly. In addition, the vinyl groups in silicone oil are necessary. During the curing of silicone rubber, condensed aromatics could be introduced into the molecular network of silicone rubber by the reaction of vinyl groups in C_1 gum, C_2 gum and C_3 gum. So, their radiation protection effects could be characterized as "internal protection".
According to the experiment results, C_2 gum has the best radiation protection effects among three gums. From the UV spectra, it can be found that the aromaticity of acenaphthenyl groups in C_2 gum is the largest. But there are 30 carbon atoms in the conjugated structure of condensed aromatics in C_1 gum and C_3 gum, while 28 carbon atoms in acenaphthenyl groups in C_2 gum. So, the aromaticity of acenaphthenyl groups in C_2 gum should be the least. In order to explain the reason, quantum chemical calculation is utilized. The optimized geometrical structrures of condensed aromatics in C_1 gum, C_2 gum and C_3 gum are calculated at B3LYP/6-31G* levels. We find that some phenyl groups in acenaphthenyl groups are coplanar and have the largest conjugated structure. While all the phenyl groups in tetraphenylphenyl groups or benzophenanthrene groups are not coplanar. At the same time, by density function theory (DFT), the electronic energy gap (Eg) between HOMO and LUMO frontier molecular orbitals of condensed aromatics are calculated and the Eg of acenaphthenyl groups in C_2 gum is the smallest, which explains the reason why C_2 gum has the best radiation protection effects.
Methylphenyldichlorosilane is synthesized by Grignard reaction between methyltrichlorosiliane with bromobenzene. And the by-product with high boiling point in Grignard reaction is proved as methyldiphenylchlorosilane by ~1HNMR analysis. By the hydrolyzation of MePhSiCl_2 and Me_2SiCl_2, polymethylphenylsilicone rubber can be obtained. And the rubber containing 30 mol% phenyl groups has excellent radiation resistance, which is attributed to the phenyl groups in rubber system. For example, after 450 kGy radiation, the tensile strength decreased from 6.0 MPa to 5.4 MPa, only decreased 10%. When the content of phenyl groups in rubber system is the same, the radiation resistance of polymethylphenylsilicone rubber is a little better than that of poly(dimethyl-diphenyl)silicone rubber after higher dose radiation (900 kGy). This is attributed to the distribution of phenyl groups in rubber system.
In order to improve the radiation resistance of condensed-type RTV silicone rubber, two kinds of crosslinking agents are synthesized successfully: triethoxysilane with acenaphthenyl groups (m.p. 49℃) and triethoxysilane with benzophenanthrene groups (m.p. 76℃), characterized by IR and ~1HNMR analysis. When they are used as crosslinking agent in condensed-type RTV silicone rubber, the curing speed can be accelerated by improving the curing temperature (50-60℃). After radiation, the results show that they can effectively improve the radiation resistance of RTV silicone rubber and their suitable amount used is 14-18 phr.
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