CN106519701A - Method for preparing heatproof silicone rubber having ethyl phenyl hydrogen-assisted cage-type silsesquioxane - Google Patents
Method for preparing heatproof silicone rubber having ethyl phenyl hydrogen-assisted cage-type silsesquioxane Download PDFInfo
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- 229920002379 silicone rubber Polymers 0.000 title claims abstract description 29
- 239000004945 silicone rubber Substances 0.000 title claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 11
- 239000001257 hydrogen Substances 0.000 title claims abstract description 11
- -1 ethyl phenyl hydrogen Chemical compound 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 229920002545 silicone oil Polymers 0.000 claims abstract description 11
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 6
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 6
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 5
- 239000010703 silicon Substances 0.000 claims abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 9
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- 238000013019 agitation Methods 0.000 claims 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 239000003060 catalysis inhibitor Substances 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract description 2
- 238000004073 vulcanization Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
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Abstract
一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法，涉及一种硅橡胶制备方法，本发明中硅橡胶由甲基苯基乙烯基硅油，乙苯基氢基笼型倍半硅氧烷交联剂，金属氧化物，PC610催化剂抑制剂，在Pt催化剂作用下反应得到。本发明将既含有苯环又含有硅氢基的笼型倍半硅氧烷（苯环和硅氢键的个数由笼型八氢基倍半硅氧烷和苯乙烯的摩尔比决定）引入到硅橡胶当中，笼型倍半硅氧烷和硅橡胶中乙烯基发生加成反应，提高了硅橡胶的交联密度，制备出具有良好热稳定性和力学性能的POSS增强型的新型室温硫化硅橡胶。A method for preparing heat-resistant silicone rubber with ethylphenylhydrogen cage-type silsesquioxane, relating to a method for preparing silicone rubber. In the present invention, the silicone rubber is composed of methylphenyl vinyl silicone oil, ethylphenylhydrogen group Cage silsesquioxane crosslinking agent, metal oxide, PC610 catalyst inhibitor, obtained by reaction under the action of Pt catalyst. The present invention introduces cage silsesquioxane containing both benzene ring and silicon hydrogen group (the number of benzene ring and silicon hydrogen bond is determined by the molar ratio of cage octahydrosilsesquioxane and styrene) Addition reaction between cage silsesquioxane and vinyl in silicone rubber increases the cross-linking density of silicone rubber, and prepares a new POSS-enhanced room temperature vulcanization with good thermal stability and mechanical properties. Silicone Rubber.
Description
技术领域technical field
本发明涉及一种硅橡胶制备方法，特别是涉及一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法。The invention relates to a method for preparing silicone rubber, in particular to a method for preparing heat-resistant silicone rubber with ethylphenyl hydrogen group cage type silsesquioxane.
背景技术Background technique
随着现代工业的发展硅橡胶的应用领域越来越广，作为航天航空军事电子电器发动机工业的主要零部件的材料，随着主机性能的提升相应对零部件材料性能的要求越来越苛刻，现有的硅橡胶已无法满足更加严格的耐高温性能要求，直接阻碍了相关产业的发展。因而开发出一种耐高温，力学性能好的硅橡胶成为了当前的研究热点。With the development of modern industry, the application field of silicone rubber is becoming wider and wider. As the main component material of the aerospace military electronic and electrical engine industry, with the improvement of the performance of the main engine, the requirements for the performance of the component materials are becoming more and more stringent. Existing silicone rubber can no longer meet the more stringent high temperature performance requirements, which directly hinders the development of related industries. Therefore, the development of a silicone rubber with high temperature resistance and good mechanical properties has become a current research hotspot.
发明内容Contents of the invention
本发明的目的在于提供一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法，该方法在笼型倍半硅氧烷无机骨架的基础上，还嵌入了苯环，两种结构相互协同作用，大大提高硅橡胶耐热温度及其力学性能。The object of the present invention is to provide a method for preparing heat-resistant silicone rubber with ethylphenylhydrogen cage silsesquioxane, which is based on the inorganic skeleton of cage silsesquioxane and benzene ring , The two structures work together to greatly improve the heat-resistant temperature and mechanical properties of silicone rubber.
本发明的目的是通过以下技术方案实现的：The purpose of the present invention is achieved through the following technical solutions:
一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法，由以下步骤制备的：A preparation method for heat-resistant silicone rubber with ethylphenylhydrogen cage silsesquioxane, prepared by the following steps:
i）乙苯基氢基笼型倍半硅氧烷的合成；i) Synthesis of ethylphenylhydrogen cage silsesquioxane;
ii）依次加入多乙烯基硅油，金属氧化物，PC610抑制剂，Pt铂金催化剂，机械搅拌混合均匀，100℃真空除水5h；再加入上述制备的溶于甲苯的含有乙苯基氢基笼型倍半硅氧烷有机硅交联剂，混合均匀后低压除去体系中的气泡，再于100℃下热处理4h后即可完全固化；ii) Add polyvinyl silicone oil, metal oxide, PC610 inhibitor, Pt platinum catalyst in sequence, mechanically stir and mix well, remove water under vacuum at 100°C for 5 hours; Silsesquioxane organosilicon crosslinking agent, after mixing evenly, remove the air bubbles in the system under low pressure, and then heat treatment at 100°C for 4 hours to completely cure;
反应方程式如下：The reaction equation is as follows:
。 .
所述的一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法，多乙烯基硅油为甲基苯基乙烯基硅油，粘度为30200mPa·s，苯基质量分数为55%，乙烯基质量分数为3.6%；In the preparation method of heat-resistant silicone rubber with ethylphenylhydrogen cage silsesquioxane, the polyvinyl silicone oil is methylphenylvinyl silicone oil, the viscosity is 30200mPa·s, and the mass fraction of phenyl groups is 55%, vinyl mass fraction is 3.6%;
所述的一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法，金属氧化物是Fe2O3、 CeO2、 ZnO、 TiO2、 V2O5，上述氧化物采用单独一种或两种以上，其颗粒度为 0.1～5μm 范围。In the method for preparing heat-resistant silicone rubber with ethylphenylhydrogen cage silsesquioxane, the metal oxides are Fe 2 O 3 , CeO 2 , ZnO, TiO 2 , V 2 O 5 , and the above oxidation One kind or more than two kinds of substances are used, and the particle size is in the range of 0.1-5 μm.
所述的一种带有乙苯基氢基笼型倍半硅氧烷耐热硅橡胶制备方法，上述反应中八氢基笼型倍半硅氧烷和苯乙烯按1：n的摩尔比进行反应n=1,2,3,4,5,6,7,8，根据反应的摩尔比不同，反应产物如上式R基的个数及位置也不同（苯环和氢键的个数由笼型八氢基倍半硅氧烷和苯乙烯的摩尔比决定），在用作硅橡胶交联剂是n不等于8，所以反应式是以摩尔比为1:1反应为例的。The preparation method of heat-resistant silicone rubber with ethylphenylhydrogen cage silsesquioxane, in the above reaction, octahydro cage silsesquioxane and styrene are carried out in a molar ratio of 1:n Reaction n=1, 2, 3, 4, 5, 6, 7, 8, according to the different molar ratios of the reaction, the number and position of the reaction product such as the above formula R groups are also different (the number of benzene rings and hydrogen bonds is determined by the cage The molar ratio of type octahydrosilsesquioxane and styrene is determined), and n is not equal to 8 when used as a silicone rubber crosslinking agent, so the reaction formula is based on a molar ratio of 1:1 as an example.
本发明的优点与效果是：Advantage and effect of the present invention are:
本发明中硅橡胶由甲基苯基乙烯基硅油，乙苯基氢基笼型倍半硅氧烷交联剂，金属氧化物，PC610催化剂抑制剂，在Pt催化剂作用下反应得到。本发明将既含有苯环又含有硅氢基的笼型倍半硅氧烷（苯环和硅氢键的个数由笼型八氢基倍半硅氧烷和苯乙烯的摩尔比决定）引入到硅橡胶当中，笼型倍半硅氧烷和硅橡胶中乙烯基发生加成反应，提高了硅橡胶的交联密度，制备出具有良好热稳定性和力学性能的POSS增强型的新型室温硫化硅橡胶。The silicone rubber in the present invention is obtained by reacting methylphenyl vinyl silicone oil, ethylphenylhydrogen-cage silsesquioxane crosslinking agent, metal oxide, and PC610 catalyst inhibitor under the action of Pt catalyst. The present invention introduces cage silsesquioxane containing both benzene ring and silicon hydrogen group (the number of benzene ring and silicon hydrogen bond is determined by the molar ratio of cage octahydrosilsesquioxane and styrene) Addition reaction between cage silsesquioxane and vinyl in silicone rubber increases the cross-linking density of silicone rubber, and prepares a new POSS-enhanced room temperature vulcanization with good thermal stability and mechanical properties. Silicone Rubber.
具体实施方式detailed description
下面结合实施例对本发明进行详细说明。The present invention will be described in detail below in conjunction with examples.
实施例中原料除特殊说明，均为市购。Unless otherwise specified, the raw materials in the examples are commercially available.
实施例中所用交联剂乙苯基氢基笼型倍半硅氧烷是由八氢基笼型倍半硅氧烷和苯乙烯按1：4的摩尔比进行反应得到的。The cross-linking agent ethylphenylhydrogen cage silsesquioxane used in the examples is obtained by reacting octahydro cage silsesquioxane and styrene at a molar ratio of 1:4.
实施例1Example 1
取100份甲基苯基乙烯基硅油，5份纳米氧化锡，5份纳米氧化铈,0.2份PC610，0.5份Pt铂金催化剂, 机械搅拌混合均匀,100℃真空除水5h。再加入35份溶于甲苯中的乙苯基氢基笼型倍半硅氧烷有机硅交联剂，混合均匀后低压除去体系中的气泡；再于100℃下热处理4h后即可完全固化。按照GB/T 13477.6-2002测试所得固化后胶体的性能。Take 100 parts of methyl phenyl vinyl silicone oil, 5 parts of nano-tin oxide, 5 parts of nano-cerium oxide, 0.2 part of PC610, 0.5 part of Pt platinum catalyst, stir and mix evenly, and remove water in vacuum at 100 ° C for 5 hours. Then add 35 parts of ethylphenylhydrogen cage silsesquioxane organosilicon crosslinking agent dissolved in toluene, mix evenly and remove air bubbles in the system under low pressure; heat treatment at 100°C for 4 hours and then completely solidify. According to GB/T 13477.6-2002, test the properties of the cured colloid.
实施例2Example 2
取100份甲基苯基乙烯基硅油，5份纳米氧化锡，5份纳米氧化铈,0.2份PC610，0.5份Pt铂金催化剂, 机械搅拌混合均匀,100℃真空除水5h。再加入45份溶于甲苯中的乙苯基氢基笼型倍半硅氧烷有机硅交联剂，混合均匀后低压除去体系中的气泡；再于100℃下热处理4h后即可完全固化。按照GB/T 13477.6-2002测试所得固化后胶体的性能。Take 100 parts of methyl phenyl vinyl silicone oil, 5 parts of nano-tin oxide, 5 parts of nano-cerium oxide, 0.2 part of PC610, 0.5 part of Pt platinum catalyst, stir and mix evenly, and remove water in vacuum at 100 ° C for 5 hours. Then add 45 parts of ethylphenylhydrogen cage silsesquioxane organosilicon crosslinking agent dissolved in toluene, mix evenly and remove air bubbles in the system under low pressure; heat treatment at 100°C for 4 hours and then completely solidify. According to GB/T 13477.6-2002, test the properties of the cured colloid.
实施例3Example 3
取100份甲基苯基乙烯基硅油，5份纳米氧化锡，5份纳米氧化铈,0.2份PC610，0.5份Pt铂金催化剂, 机械搅拌混合均匀,100℃真空除水5h。再加入55份溶于甲苯中的乙苯基氢基笼型倍半硅氧烷有机硅交联剂，混合均匀后低压除去体系中的气泡；再于100℃下热处理4h后即可完全固化。按照GB/T 13477.6-2002测试所得固化后胶体的性能：Take 100 parts of methyl phenyl vinyl silicone oil, 5 parts of nano-tin oxide, 5 parts of nano-cerium oxide, 0.2 part of PC610, 0.5 part of Pt platinum catalyst, stir and mix evenly, and remove water in vacuum at 100 ° C for 5 hours. Then add 55 parts of ethylphenylhydrogen cage silsesquioxane organosilicon crosslinking agent dissolved in toluene, mix evenly and remove air bubbles in the system under low pressure; heat treatment at 100°C for 4 hours and then completely solidify. According to GB/T 13477.6-2002 test the properties of the cured colloid:
由以上数据可知，本发明用乙苯基氢基笼型倍半硅氧烷制备得到的硅橡胶，耐热性能优异，力学性能良好。It can be seen from the above data that the silicone rubber prepared by using ethylphenylhydrogen cage silsesquioxane in the present invention has excellent heat resistance and good mechanical properties.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108913089A (en) * | 2018-07-23 | 2018-11-30 | 深圳天鼎新材料有限公司 | Two-component packaging plastic, preparation method and application method and application |
| CN110387054A (en) * | 2019-08-14 | 2019-10-29 | 北京化工大学 | A preparation method of low-cost transparent hybrid silicone rubber |
| CN110536933A (en) * | 2017-04-26 | 2019-12-03 | 信越化学工业株式会社 | Addition curable silicone rubber compound |
| CN112888715A (en) * | 2018-10-18 | 2021-06-01 | 东亚合成株式会社 | Silsesquioxane derivative composition and use thereof |
Citations (1)
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|---|---|---|---|---|
| CN104327273A (en) * | 2014-10-22 | 2015-02-04 | 上海大学 | Organic silicon potting adhesive containing POSS group and preparation method of organic silicon potting adhesive |
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- 2016-10-21 CN CN201610918247.0A patent/CN106519701A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104327273A (en) * | 2014-10-22 | 2015-02-04 | 上海大学 | Organic silicon potting adhesive containing POSS group and preparation method of organic silicon potting adhesive |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110536933A (en) * | 2017-04-26 | 2019-12-03 | 信越化学工业株式会社 | Addition curable silicone rubber compound |
| CN110536933B (en) * | 2017-04-26 | 2022-04-01 | 信越化学工业株式会社 | Addition curing type silicone rubber composition |
| CN108913089A (en) * | 2018-07-23 | 2018-11-30 | 深圳天鼎新材料有限公司 | Two-component packaging plastic, preparation method and application method and application |
| CN112888715A (en) * | 2018-10-18 | 2021-06-01 | 东亚合成株式会社 | Silsesquioxane derivative composition and use thereof |
| CN112888715B (en) * | 2018-10-18 | 2023-11-03 | 东亚合成株式会社 | Silsesquioxane derivative compositions and uses thereof |
| CN110387054A (en) * | 2019-08-14 | 2019-10-29 | 北京化工大学 | A preparation method of low-cost transparent hybrid silicone rubber |
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Application publication date: 20170322 |