氢化共轭二烯烃类聚合物的制备与应用
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摘要
共轭二烯烃类聚合物,特别是橡胶类聚合物的氢化反应,由于其为橡胶带来新的结构和性能的改进,长久以来一直是很活跃的研究领域。将活性阴离子可控聚合技术和氢化反应技术相结合来合成结构可控的饱和的烯烃共聚物是一个重要的研究方向。本论文以催化加氢反应为主线,采用低成本、高活性、在环己烷中溶解性好的环烷酸镍(Ni)／三异丁基铝(Al)为催化体系对一系列均聚物、嵌段共聚物和无规共聚物进行氢化反应,重点考察了Al／Ni催化体系的反应条件对氢化反应的影响规律,制备了多种新型结构的高分子材料。
对均聚物(聚丁二烯PB和聚异戊二烯PI)分别进行氢化和氘化反应,制备了设定分子量且单分散的聚乙烯(HPB)、氘代聚乙烯(DPB)、乙烯-丙烯交替共聚物(HPI)和氘代乙烯-丙烯交替共聚物(DPI),为中子示踪研究聚集态结构提供了模板聚合物。采用上述催化体系对顺-1,4结构含量为100%的全顺式聚异戊二烯(HCPI)进行氢化反应,首次制备了具有完全交替结构的乙烯-丙烯交替共聚物；对立构嵌段聚丁二烯(LVPB-b-HVPB)进行氢化反应,制备了一系列不同嵌段比的聚乙烯-b-聚丁烯-1嵌段共聚物(PE-b-PBt-1),并将其作为聚丙烯／低密度聚乙烯(PP/LLDPE)的增容剂进行了研究；对高顺式聚异戊二烯-b-聚己内酯嵌段共聚物(HCPI-b-PCL)进行氢化反应制备了乙烯-丙烯交替共聚物-b-聚己内酯两嵌段共聚物(alt-EP-b-PCL);对苯乙烯-异戊二烯-丁二烯三元无规共聚物(SIBR)进行氢化反应制备了氢化SIBR(HSIBR)。将星形乙烯-丙烯交替共聚物(S-alt-EP)、线形HSIBR和星形HSIBR(S-HSIBR)三种氢化产品用作润滑油的黏度指数改进剂,对其微观结构与性能的关系进行了研究。HSIBR作为新型材料,研究了其单体含量和加氢度对于抗热氧稳定性和物理机械性能的影响。主要研究结果及结论如下：
以均聚物(PB、PI和HCPI)为氢化反应底物,得到完全氢化或氘化的产物。研究了Al／Ni催化体系中反应条件对于聚丁二烯氢化反应的影响,得出了最佳反应条件如下：Ni用量为2mgNi／g聚合物、Al/Ni比为6、反应温度为70℃、反应压力为4MPa、反应时间3h。
以嵌段共聚物(LVPB-b-HVPB和HCPI-b-PCL)为氢化底物,制备了难以通过单体直接聚合得到的结构可控的饱和的烯烃共聚物(PE-b-PBt-1和alt-EP-b-PCL)。PE-b-PBt-1可作为PP/LLDPE共混物的增容剂,冲击强度和断裂伸长率随增容剂含量的增加而增加。在PP/LLDPE摩尔比为8：2的共混体系中PE嵌段含量越低的增容剂增容效果越好,共混物的力学性能越优异。通过NMR, FTIR和广角X射线衍射测试,结果表明alt-EP-b-PCL为具有高度规整的序列结构的嵌段共聚物。
以系列化的SIBR为底物进行氢化反应,制备一系列HSIBR。研究了反应条件对SIBR氢化反应的影响规律,确定了最优反应条件：Ni用量为2mgNi／g聚合物、Al／Ni比为6、反应温度为60℃、反应压力为4MPa、聚合物浓度为10%、反应时间3h。在上述氢化条件下SIBR加氢度大于98%。研究了SIBR氢化反应的动力学,通过1H NMR测试得到了SIBR中各微观结构的氢化反应速率大小顺序依次为：B1,2>B1,4>13,4>11,4。
HSIBR用作润滑油黏度指数改进剂(viscosity index improver, VII),重点考察HSIBR分子量、微观结构和SIBR中聚丁二烯单元含量对VII黏度指数改进剂性能的影响规律进行了研究。结果表明,HSIBR是一种具有非常突出的剪切稳定性和低温性能的黏度指数改进剂。
HSIBR作为新型材料,对不同单体配比和不同加氢度的胶样进行开炼硫化,对样品的热空气老化性能、拉伸强度和硬度进行了研究。结果表明,随着异戊二烯含量增加,样品硬度增大,tanδ峰值增加；随着加氢度增加,氢化样品硬度降低,抗老化性能显著提高,tanδ峰值先降低后升高,储能模量E’不断降低,损耗模量E”峰值不断降低。
Hydrogenation reaction of conjugated diene polymer, especially rubber-like polymer, has been an active field of research for a long time because hydrogenated rubbers include new or improved properties comparing to the base rubbers. Combination of living anionic polymerization and hydrogenation reaction for preparation of saturated olefin copolymers with a controlled architecture is an important research field. In this paper, throughout catalytic hydrogenation reaction, a series of homopolymer, block copolymer and random copolymer were hydrogenated by a Ziegler-Natta type catalyst with low cost, high activity and good solubility in cyclohexane, which was prepared with nickel naphthenate (Ni) as main catalyst and aluminum triisobutyl (Al) as assist catalyst. The effect of reaction condition on the extent of hydrogenation was investigated. A series of polymer materials with new structure were prepared.
Designed molecular weight and monodisperse hydrogenated polybutadiene (HPB), deuterated polybutadiene (DPB), hydrogenated polyisoprene (HPI) and deuterated polyisoprene (DPI) were prepared by hydrogenation or deuteration of homopolymers (polybutadiene and polyisoprene). Alternating ethylene-propylene copolymer (alt-EP) was prepared for the first time by hydrogenation of polyisoprene (HCPI) having high cis-1,4content (～100%) with the catalyst mentioned above. A series of polyethylene-b-polybutylene (PE-b-PBt-1) samples with different block ratio were prepared by hydrogenation of low-vinyl-polybutadiene-b-high-vinyl-polybutadiene (LVPB-b-HVPB), which can be used as compatibilizer of polypropylene/linear low density polyethylene (PP/LLDPE). High cis-polyisoprene-b-polycaprolactone (HCPI-b-PCL), and styrene-isoprene-butadiene rubber (SIBR) were hydrogenated to prepare new materials. Star-shaped alt-EP (S-alt-EP), hydrogenated SIBR (HSIBR) and star-shaped HSIBR (S-HSIBR) can be used as viscosity index improver (VII) in lubricants due to their improved thermal and oxidative resistance. The relationship of microstructure and performance was investigated. When HSIBR was used as damping material, the effect of monomer content and hydrogenation degree on thermal oxidative stability and dynamic mechanical property was investigated. The main results and conclusions are as follows:
The fully hydrogenated or deuterated products were obtained using homopolymer as hydrogenation substrate. The effect of reaction condition on the extent of hydrogenation was investigated. The optimum hydrogenation condition was as follows:catalyst amount,2mg Ni per each1gram of polymer; Al/Ni molar ratio,6; temperature,70℃; hydrogen pressure,4MPa; and time,3h.
PE-b-PBt-1and alt-EP-b-PCL were prepared by hydrogenation using block copolymer as hydrogenation substrate. Used as compatibilizer of PP/LLDPE, impact strength and breaking elongation of blend increased with the increase of the compatibilizer content. In the blend with the PP/LLDPE molar ratio of8:2, compatibilization effect and mechanical properties increased with the decrease of PE block content in solubilizer.The results obtained from NMR, FTIR and WAXD indicated that alt-EP-b-PCL was block copolymer having high alternating ethylene and propylene block.
HSIBR was prepared by hydrogenation using random terpolymer (SIBR) as hydrogenation substrate. The effect of reaction condition on the extent of hydrogenation of SIBR was investigated. The optimum hydrogenation condition was as follows:catalyst amount,2mg Ni per each1gram of polymer; Al/Ni molar ratio,6; temperature,60℃; hydrogen pressure,4MPa; polymer concentration,10%; and time,3h. HSIBR with hydrogenation degree of98%was obtained in the hydrogenation condition as mentioned above. Hydrogenation reaction kinetics of SIBR was also investigated in this paper. The results obtained from1H NMR indicated that the hydrogenation rates of microstructures decreased as follow:B1,2>B1,4>Ⅰ3,4>Ⅰ1,4.
HSIBR can be used as Ⅶ in lubricant. The effect of molecular weight, microstructure and butadiene units content of HSIBR on performance as Ⅶ was investigated in this paper. The results indicated that HSIBR was a Ⅶ with outstanding shear stability and high HTHS viscosities, while maintaining correspondingly high thickening power and viscosity index, as well as excellent low-temperature fluidity.
HSIBR can also be used as damping material. After mixing and vulcanizing, hydrogenated samples with different monomer ratio and different hydrogenation degree was obtained. Physical mechanical properties such as, aging, tensile and hardness (Shore A) experiments were investigated. The results indicated that with the increase of isoprene unit content, hardness of samples increased, the peak value of tan δ increased, and that with the increase of hydrogenation degree, hardness of samples decreased, aging property was improverd, the peak value of tan δ increased first, then decreased, storage modulus (E') decreased, loss modulus (E") decreased first, then increased. Content of isoprene play a very important role in damping capacity of polymer. Hydrogenated product obtain from SIBR with high isoprene content could be suitable for damping materials.
对均聚物(聚丁二烯PB和聚异戊二烯PI)分别进行氢化和氘化反应,制备了设定分子量且单分散的聚乙烯(HPB)、氘代聚乙烯(DPB)、乙烯-丙烯交替共聚物(HPI)和氘代乙烯-丙烯交替共聚物(DPI),为中子示踪研究聚集态结构提供了模板聚合物。采用上述催化体系对顺-1,4结构含量为100%的全顺式聚异戊二烯(HCPI)进行氢化反应,首次制备了具有完全交替结构的乙烯-丙烯交替共聚物；对立构嵌段聚丁二烯(LVPB-b-HVPB)进行氢化反应,制备了一系列不同嵌段比的聚乙烯-b-聚丁烯-1嵌段共聚物(PE-b-PBt-1),并将其作为聚丙烯／低密度聚乙烯(PP/LLDPE)的增容剂进行了研究；对高顺式聚异戊二烯-b-聚己内酯嵌段共聚物(HCPI-b-PCL)进行氢化反应制备了乙烯-丙烯交替共聚物-b-聚己内酯两嵌段共聚物(alt-EP-b-PCL);对苯乙烯-异戊二烯-丁二烯三元无规共聚物(SIBR)进行氢化反应制备了氢化SIBR(HSIBR)。将星形乙烯-丙烯交替共聚物(S-alt-EP)、线形HSIBR和星形HSIBR(S-HSIBR)三种氢化产品用作润滑油的黏度指数改进剂,对其微观结构与性能的关系进行了研究。HSIBR作为新型材料,研究了其单体含量和加氢度对于抗热氧稳定性和物理机械性能的影响。主要研究结果及结论如下：
以均聚物(PB、PI和HCPI)为氢化反应底物,得到完全氢化或氘化的产物。研究了Al／Ni催化体系中反应条件对于聚丁二烯氢化反应的影响,得出了最佳反应条件如下：Ni用量为2mgNi／g聚合物、Al/Ni比为6、反应温度为70℃、反应压力为4MPa、反应时间3h。
以嵌段共聚物(LVPB-b-HVPB和HCPI-b-PCL)为氢化底物,制备了难以通过单体直接聚合得到的结构可控的饱和的烯烃共聚物(PE-b-PBt-1和alt-EP-b-PCL)。PE-b-PBt-1可作为PP/LLDPE共混物的增容剂,冲击强度和断裂伸长率随增容剂含量的增加而增加。在PP/LLDPE摩尔比为8：2的共混体系中PE嵌段含量越低的增容剂增容效果越好,共混物的力学性能越优异。通过NMR, FTIR和广角X射线衍射测试,结果表明alt-EP-b-PCL为具有高度规整的序列结构的嵌段共聚物。
以系列化的SIBR为底物进行氢化反应,制备一系列HSIBR。研究了反应条件对SIBR氢化反应的影响规律,确定了最优反应条件：Ni用量为2mgNi／g聚合物、Al／Ni比为6、反应温度为60℃、反应压力为4MPa、聚合物浓度为10%、反应时间3h。在上述氢化条件下SIBR加氢度大于98%。研究了SIBR氢化反应的动力学,通过1H NMR测试得到了SIBR中各微观结构的氢化反应速率大小顺序依次为：B1,2>B1,4>13,4>11,4。
HSIBR用作润滑油黏度指数改进剂(viscosity index improver, VII),重点考察HSIBR分子量、微观结构和SIBR中聚丁二烯单元含量对VII黏度指数改进剂性能的影响规律进行了研究。结果表明,HSIBR是一种具有非常突出的剪切稳定性和低温性能的黏度指数改进剂。
HSIBR作为新型材料,对不同单体配比和不同加氢度的胶样进行开炼硫化,对样品的热空气老化性能、拉伸强度和硬度进行了研究。结果表明,随着异戊二烯含量增加,样品硬度增大,tanδ峰值增加；随着加氢度增加,氢化样品硬度降低,抗老化性能显著提高,tanδ峰值先降低后升高,储能模量E’不断降低,损耗模量E”峰值不断降低。
Hydrogenation reaction of conjugated diene polymer, especially rubber-like polymer, has been an active field of research for a long time because hydrogenated rubbers include new or improved properties comparing to the base rubbers. Combination of living anionic polymerization and hydrogenation reaction for preparation of saturated olefin copolymers with a controlled architecture is an important research field. In this paper, throughout catalytic hydrogenation reaction, a series of homopolymer, block copolymer and random copolymer were hydrogenated by a Ziegler-Natta type catalyst with low cost, high activity and good solubility in cyclohexane, which was prepared with nickel naphthenate (Ni) as main catalyst and aluminum triisobutyl (Al) as assist catalyst. The effect of reaction condition on the extent of hydrogenation was investigated. A series of polymer materials with new structure were prepared.
Designed molecular weight and monodisperse hydrogenated polybutadiene (HPB), deuterated polybutadiene (DPB), hydrogenated polyisoprene (HPI) and deuterated polyisoprene (DPI) were prepared by hydrogenation or deuteration of homopolymers (polybutadiene and polyisoprene). Alternating ethylene-propylene copolymer (alt-EP) was prepared for the first time by hydrogenation of polyisoprene (HCPI) having high cis-1,4content (～100%) with the catalyst mentioned above. A series of polyethylene-b-polybutylene (PE-b-PBt-1) samples with different block ratio were prepared by hydrogenation of low-vinyl-polybutadiene-b-high-vinyl-polybutadiene (LVPB-b-HVPB), which can be used as compatibilizer of polypropylene/linear low density polyethylene (PP/LLDPE). High cis-polyisoprene-b-polycaprolactone (HCPI-b-PCL), and styrene-isoprene-butadiene rubber (SIBR) were hydrogenated to prepare new materials. Star-shaped alt-EP (S-alt-EP), hydrogenated SIBR (HSIBR) and star-shaped HSIBR (S-HSIBR) can be used as viscosity index improver (VII) in lubricants due to their improved thermal and oxidative resistance. The relationship of microstructure and performance was investigated. When HSIBR was used as damping material, the effect of monomer content and hydrogenation degree on thermal oxidative stability and dynamic mechanical property was investigated. The main results and conclusions are as follows:
The fully hydrogenated or deuterated products were obtained using homopolymer as hydrogenation substrate. The effect of reaction condition on the extent of hydrogenation was investigated. The optimum hydrogenation condition was as follows:catalyst amount,2mg Ni per each1gram of polymer; Al/Ni molar ratio,6; temperature,70℃; hydrogen pressure,4MPa; and time,3h.
PE-b-PBt-1and alt-EP-b-PCL were prepared by hydrogenation using block copolymer as hydrogenation substrate. Used as compatibilizer of PP/LLDPE, impact strength and breaking elongation of blend increased with the increase of the compatibilizer content. In the blend with the PP/LLDPE molar ratio of8:2, compatibilization effect and mechanical properties increased with the decrease of PE block content in solubilizer.The results obtained from NMR, FTIR and WAXD indicated that alt-EP-b-PCL was block copolymer having high alternating ethylene and propylene block.
HSIBR was prepared by hydrogenation using random terpolymer (SIBR) as hydrogenation substrate. The effect of reaction condition on the extent of hydrogenation of SIBR was investigated. The optimum hydrogenation condition was as follows:catalyst amount,2mg Ni per each1gram of polymer; Al/Ni molar ratio,6; temperature,60℃; hydrogen pressure,4MPa; polymer concentration,10%; and time,3h. HSIBR with hydrogenation degree of98%was obtained in the hydrogenation condition as mentioned above. Hydrogenation reaction kinetics of SIBR was also investigated in this paper. The results obtained from1H NMR indicated that the hydrogenation rates of microstructures decreased as follow:B1,2>B1,4>Ⅰ3,4>Ⅰ1,4.
HSIBR can be used as Ⅶ in lubricant. The effect of molecular weight, microstructure and butadiene units content of HSIBR on performance as Ⅶ was investigated in this paper. The results indicated that HSIBR was a Ⅶ with outstanding shear stability and high HTHS viscosities, while maintaining correspondingly high thickening power and viscosity index, as well as excellent low-temperature fluidity.
HSIBR can also be used as damping material. After mixing and vulcanizing, hydrogenated samples with different monomer ratio and different hydrogenation degree was obtained. Physical mechanical properties such as, aging, tensile and hardness (Shore A) experiments were investigated. The results indicated that with the increase of isoprene unit content, hardness of samples increased, the peak value of tan δ increased, and that with the increase of hydrogenation degree, hardness of samples decreased, aging property was improverd, the peak value of tan δ increased first, then decreased, storage modulus (E') decreased, loss modulus (E") decreased first, then increased. Content of isoprene play a very important role in damping capacity of polymer. Hydrogenated product obtain from SIBR with high isoprene content could be suitable for damping materials.
引文
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