聚烯烃弹性体与乙烯基单体接枝反应及其接枝产物对SAN树脂增韧作用的研究
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摘要
聚烯烃弹性体分子链因没有碳-碳双键或碳-碳双键含量低而具有优异的耐老化性能。用聚烯烃弹性体与乙烯基单体的接枝改性产物对塑料进行共混改性，可制备出耐气候老化黄变性能优异的高抗冲工程塑料，广泛用于制造汽车及其他机动车配件和露天构件，应用前景广阔。聚烯烃弹性体与乙烯基单体接枝共聚的反应行为和反应机理鲜有报道，研究其反应行为和反应机理有助于掌握和控制接枝共聚的反应过程及接枝产物的结构、形态和性质，具有重要的理论意义和实践价值。
本文以BPO为引发剂分别引发EPDM/St-AN、EPDM/St、EPDM/MMA、EPM/St-AN、PEB/MMA-AN和IIR/MMA-AN的悬浮体系与EPDM/MMA的溶液体系共7个体系在80℃下进行自由基接枝共聚反应，对每个体系以不同聚合反应时间合成了一系列的接枝共聚反应产物，将产物的各组分逐一分离，建立了体系的单体转化率（CR）、平均接枝率（GRa）、接枝效率（GE）、单体接枝转化率（CRg）、单体非接枝转化率（CRf）、橡胶接枝率（GRr）、真实接枝率（GRt）和凝胶率（CPR）与反应时间的关系曲线。用GPC、FTIR和1H-NMR等现代测试分析技术对产物各组分进行表征，为探明各体系的基元反应和反应机理提供了可靠的实验依据。结果表明，各体系在反应初期就发生弹性体/单体的自由基链转移接枝聚合和单体非接枝聚合的竞争反应，并且除IIR/MMA-AN悬浮体系外，其余6个体系的自由基链转移接枝的反应速率都明显高于单体非接枝聚合的反应速率。各体系的自由基链转移接枝反应基本都在反应时间为100min左右停止。建立了弹性体/单体自由基链转移接枝反应行为的蜷曲线团粒子模型，成功地阐释了各体系自由基链转移接枝反应快速进行和停止的机理。
通过研究体系的平均接枝率GRa随反应时间的延长变化的规律，根据体系的自由基链转移接枝反应停止后，体系的GRa仍然继续提高的事实，分析了反应过程中体系可能发生的接枝基元反应。结果表明，各个体系除在反应初始阶段都发生自由基链转移接枝这一基元反应外，还会发生接枝共聚物的接枝链与游离聚合物“嫁接”和“架桥”交联的接枝基元反应。其中，EPDM/St-AN和EPDM/MMA悬浮体系先发生了“嫁接”反应后发生了“架桥”交联反应，并推导了“嫁接”和“架桥”的化学反应方程式；EPDM/St悬浮体系因St单元的苯环无反应活性而既无“嫁接”反应也无“架桥”交联反应，但存在热引发接枝反应；而其他体系则只有“嫁接”反应而无“架桥”交联反应。
用GPC分析了接枝共聚反应初期生成的游离聚合物，发现在其谱图上出现两个分子量分布峰，证实低分子量分布峰是表征链增长自由基向弹性体大分子链转移终止形成的低聚物。根据这一发现和自由基链转移接枝反应机理，推导出计算接枝链分子量的普适公式为M g, n=m g M L, n/(m f r)，用该公式计算了7个体系的接枝链的数均分子量。结果表明，接枝链的数均分子量显著大于由链增长自由基链转移终止形成的低聚物的数均分子量，而普遍小于由链增长自由基双基终止形成的游离聚合物的数均分子量。
研究了7个体系的GRr、接枝链的分子量、游离聚合物的分子量和未接枝橡胶的分子量随反应时间的延长而变化的规律，发现在自由基链转移接枝反应停止后，除EPDM/St悬浮体系外，各体系都发生已接枝橡胶和未接枝橡胶大分子断链随机再接生成多“嵌段”共聚物，导致GRr进一步显著提高的反应。推导了断链随机再接形成多“嵌段”共聚物的化学反应方程式。
研究了产物与SAN树脂共混物的缺口冲击强度与体系的反应行为之间的关系，发现影响产物对SAN树脂增韧效率的主要因素是产物的GRr及其通过“架桥”交联形成的凝胶结构：对于同一体系，GRr较高的产物对SAN树脂具有更高的增韧效率；对于不同体系，含有通过“架桥”交联形成的凝胶结构的产物对SAN树脂具有更高的增韧效率。TEM分析表明，随着合成产物反应时间的延长，其共混物的橡胶相的相畴尺寸逐渐减小，缺口冲击强度逐渐提高；其中具有包藏结构的粒状分散相对共混物的增韧效率最高。SEM分析表明，当共混物冲击断面的基体发生以“冷拉伸”为特征的高度剪切屈服时，其缺口冲击强度达到最高水平。用FTIR和1H-NMR定量分析法研究了游离共聚物和接枝链各自的共组成比随反应时间的延长而发生的变化，为分析产物与SAN树脂的相容性提供了依据。DMA分析表明，接枝共聚物能显著改善橡胶与SAN树脂之间的相容性。熔体流动速率（MFR）测试表明，各体系产物与SAN树脂共混物的MFR随着合成产物反应时间的延长而降低。
研究了产物的回收方法对产物结构与性能的影响。发现“加入链终止剂且在常温干燥”的产物回收方法有效地避免了残留BPO在产物回收过程中所引发的后续副反应，从而可以更加真实地反映接枝共聚体系的反应行为和反应机理；“不加入链终止剂，在80℃干燥8h”的产物回收方法导致产物的结构与性能发生深刻的变化。
Polyolefin elastomers are endowed with excellent properties of weatherability and agingresistance due to no C=C double bond or low C=C content in their molecular chains, e.g.ethylene propylene diene terpolymer (EPDM), ethylene propylene monomer (EPM),poly(ethene-co-1-butene)(PEB) and isobutylene isoprene rubber (IIR). Graft copolymerssynthesized by grafting these polyolefin elastomers with vinyl monomers can be used ascompatibilizers and toughening agents in polymer blends to prepare high impact strengthengineering plastics of resistance against oxygen, heat, aging and yellow discoloration. Theseplastics are particularly suited for outdoor applications, such as automotive sealing systemsand roofing for buildings. Therefore, the study of the reaction mechanism of graftcopolymerization of polyolefin elastomers/vinyl monomers can not only help us understandthe reaction process of graft copolymerization and the structure and properties of the graftcopolymers, but also guide us through the synthesis of the graft copolymers that can bettersatisfy the requirement.
In this thesis, seven graft copolymerization systems, including EPDM/St-AN, EPDM/St,EPDM/MMA, EPM/St-AN, PEB/MMA-AN and IIR/MMA-AN in suspension andEPDM/MMA in solution, were carried out by free radical polymerization at80℃usingbenzoyl peroxide (BPO) as initiator. For each system, a sequential reaction products ofdifferent reaction times were synthesized. After the synthesis, each product was separated bySoxhlet extraction to obtain purified components, which were subsequently characterized byGPC, FTIR and1H-NMR analyses. The monomer conversion rate (CR), average graft ratio(GRa), graft efficiency (GE), grafted monomer conversion rate (CRg), non-grafted monomerconversion rate (CRf), rubber graft ratio (GRr), true graft ratio (GRt) and gel rate (CPR) werecalculated and plotted against the reaction time. The dependence of these reaction behaviors onreaction time was systematically investigated. The results showed that the chain transfer graftreaction (i.e.“graft from” reaction) occurred at the same time as the free polymerizationreaction at the beginning of the synthesis and stopped after about100min, and the reactionrate of the former was significantly higher than that of the latter in all systems exceptIIR/MMA-AN. A “curled-coil” model of suspension particle formed by aggregates ofmonomers, initiators, free radicals and macromolecules of the polyolefin elastomers/vinylmonomers graft copolymerization system was established to explain the above-mentionedreaction behaviors.
Based on the study of the variation of GRawith increasing reaction time and the analysisresult that GRakept rising after the “graft from” reaction stopped, we discovered that therewere still two other potential grafting elementary reactions, which we called the “graft onto”reaction and the “bridge” crosslinking reaction, occurring between the grafted chains of thegraft copolymers and the molecular chains of the free polymers via their reactive side groups.As for EPDM/St-AN and EPDM/MMA in suspension, the “bridge” crosslinking reactionoccurred after the “graft onto” reaction, and both chemical reaction equations of them werederived; however, neither of them but the suspected thermal initiation of St graftpolymerization was found in the EPDM/St suspension system, and in the other systems onlythe “graft onto” reaction was found.
GPC analysis showed that there was a bimodal molecular weight distribution of the freepolymers formed in the early stage of the reaction process, due to the co-existence of twodistinct molecular populations of low and high molecular weights, which were respectivelyformed by chain transfer termination and bi-radical termination of the free polymeric radicals.According to this discovery and the mechanism of the chain transfer graft reaction, we deriveda universal formula M g, n=m g M L, n/(m f r)to estimate the number-average molecularweight of the grafted chains of every system. The results showed that the number-averagemolecular weight of the grafted chains was much larger than that of the free polymers formedby chain transfer termination of the free polymeric radicals, and was generally smaller than thatof the free polymers formed by bi-radical termination of the free polymeric radicals.
Based on the study of the effect of reaction time on GRrand the molecular weight of thegrafted chains, the free polymers and the non-grafted rubber, we discovered that after the “graftfrom” reaction stopped, the chain scission reaction of grafted and non-grafted rubbers occurredin all systems except EPDM/St, followed by the random radical-radical combination of theresultant chain segments to form soluble “multi-block” copolymers, leading to a furthersignificant improvement of GRr. Both chemical reaction equations of them were derived.
The effect of the reaction behaviors on the notched Izod impact strength of the blendsprepared by melt blending of the reaction product and the styrene-acrylonitrile copolymers(SAN resin) was investigated. The results showed that for the same system, GRrplayed adominant role in the toughening effect of the reaction product on the SAN resin; for differentsystems, the reaction product with gel structure formed by “bridge” crosslinking reaction had ahigher toughening effect on the SAN resin. TEM analysis showed that with increasing reactiontime, the domain size of the rubber phase of the blends decreased and the notched Izod impact strength of the blends increased; the dispersed phase of rubber particles which exhibited a“salami” like structure had the highest toughening efficiency on the SAN resin. At the sametime, SEM analysis showed that the toughening mechanism of the blends was high shearyielding with “cold drawing” of the SAN matrix. The co-constitute ratio of the free copolymersand the grafted chains was measured by FTIR and1H-NMR quantitative analyses, respectively,providing experimental proof for analyzing the compatibility of the reaction product and theSAN resin. DMA analysis showed that the graft copolymers in the reaction product couldsignificantly improve the compatibility between the rubber phase and the SAN phase. Meltmass-flow rate (MFR) measurements showed that the MFR of the blends declined withincreasing reaction time.
The effect of the recovery method of the reaction product on the structure and properties ofthe reaction product was also studied. The results showed that the method, which ended thereaction using p-benzoquinone (PBQ) as terminator and dried the reaction product at roomtemperature, could effectively avoid the ensuing side reactions induced by the residual BPO inthe reaction product during the recovery process, and thus ensure the accuracy of the reactionbehaviors in the study of the reaction mechanisms of the graft copolymerization system.However, the method, which ended the reaction without using any terminator and dried thereaction product at80℃for8hours, resulted in a profound change in the structure andproperties of the reaction product.
本文以BPO为引发剂分别引发EPDM/St-AN、EPDM/St、EPDM/MMA、EPM/St-AN、PEB/MMA-AN和IIR/MMA-AN的悬浮体系与EPDM/MMA的溶液体系共7个体系在80℃下进行自由基接枝共聚反应，对每个体系以不同聚合反应时间合成了一系列的接枝共聚反应产物，将产物的各组分逐一分离，建立了体系的单体转化率（CR）、平均接枝率（GRa）、接枝效率（GE）、单体接枝转化率（CRg）、单体非接枝转化率（CRf）、橡胶接枝率（GRr）、真实接枝率（GRt）和凝胶率（CPR）与反应时间的关系曲线。用GPC、FTIR和1H-NMR等现代测试分析技术对产物各组分进行表征，为探明各体系的基元反应和反应机理提供了可靠的实验依据。结果表明，各体系在反应初期就发生弹性体/单体的自由基链转移接枝聚合和单体非接枝聚合的竞争反应，并且除IIR/MMA-AN悬浮体系外，其余6个体系的自由基链转移接枝的反应速率都明显高于单体非接枝聚合的反应速率。各体系的自由基链转移接枝反应基本都在反应时间为100min左右停止。建立了弹性体/单体自由基链转移接枝反应行为的蜷曲线团粒子模型，成功地阐释了各体系自由基链转移接枝反应快速进行和停止的机理。
通过研究体系的平均接枝率GRa随反应时间的延长变化的规律，根据体系的自由基链转移接枝反应停止后，体系的GRa仍然继续提高的事实，分析了反应过程中体系可能发生的接枝基元反应。结果表明，各个体系除在反应初始阶段都发生自由基链转移接枝这一基元反应外，还会发生接枝共聚物的接枝链与游离聚合物“嫁接”和“架桥”交联的接枝基元反应。其中，EPDM/St-AN和EPDM/MMA悬浮体系先发生了“嫁接”反应后发生了“架桥”交联反应，并推导了“嫁接”和“架桥”的化学反应方程式；EPDM/St悬浮体系因St单元的苯环无反应活性而既无“嫁接”反应也无“架桥”交联反应，但存在热引发接枝反应；而其他体系则只有“嫁接”反应而无“架桥”交联反应。
用GPC分析了接枝共聚反应初期生成的游离聚合物，发现在其谱图上出现两个分子量分布峰，证实低分子量分布峰是表征链增长自由基向弹性体大分子链转移终止形成的低聚物。根据这一发现和自由基链转移接枝反应机理，推导出计算接枝链分子量的普适公式为M g, n=m g M L, n/(m f r)，用该公式计算了7个体系的接枝链的数均分子量。结果表明，接枝链的数均分子量显著大于由链增长自由基链转移终止形成的低聚物的数均分子量，而普遍小于由链增长自由基双基终止形成的游离聚合物的数均分子量。
研究了7个体系的GRr、接枝链的分子量、游离聚合物的分子量和未接枝橡胶的分子量随反应时间的延长而变化的规律，发现在自由基链转移接枝反应停止后，除EPDM/St悬浮体系外，各体系都发生已接枝橡胶和未接枝橡胶大分子断链随机再接生成多“嵌段”共聚物，导致GRr进一步显著提高的反应。推导了断链随机再接形成多“嵌段”共聚物的化学反应方程式。
研究了产物与SAN树脂共混物的缺口冲击强度与体系的反应行为之间的关系，发现影响产物对SAN树脂增韧效率的主要因素是产物的GRr及其通过“架桥”交联形成的凝胶结构：对于同一体系，GRr较高的产物对SAN树脂具有更高的增韧效率；对于不同体系，含有通过“架桥”交联形成的凝胶结构的产物对SAN树脂具有更高的增韧效率。TEM分析表明，随着合成产物反应时间的延长，其共混物的橡胶相的相畴尺寸逐渐减小，缺口冲击强度逐渐提高；其中具有包藏结构的粒状分散相对共混物的增韧效率最高。SEM分析表明，当共混物冲击断面的基体发生以“冷拉伸”为特征的高度剪切屈服时，其缺口冲击强度达到最高水平。用FTIR和1H-NMR定量分析法研究了游离共聚物和接枝链各自的共组成比随反应时间的延长而发生的变化，为分析产物与SAN树脂的相容性提供了依据。DMA分析表明，接枝共聚物能显著改善橡胶与SAN树脂之间的相容性。熔体流动速率（MFR）测试表明，各体系产物与SAN树脂共混物的MFR随着合成产物反应时间的延长而降低。
研究了产物的回收方法对产物结构与性能的影响。发现“加入链终止剂且在常温干燥”的产物回收方法有效地避免了残留BPO在产物回收过程中所引发的后续副反应，从而可以更加真实地反映接枝共聚体系的反应行为和反应机理；“不加入链终止剂，在80℃干燥8h”的产物回收方法导致产物的结构与性能发生深刻的变化。
Polyolefin elastomers are endowed with excellent properties of weatherability and agingresistance due to no C=C double bond or low C=C content in their molecular chains, e.g.ethylene propylene diene terpolymer (EPDM), ethylene propylene monomer (EPM),poly(ethene-co-1-butene)(PEB) and isobutylene isoprene rubber (IIR). Graft copolymerssynthesized by grafting these polyolefin elastomers with vinyl monomers can be used ascompatibilizers and toughening agents in polymer blends to prepare high impact strengthengineering plastics of resistance against oxygen, heat, aging and yellow discoloration. Theseplastics are particularly suited for outdoor applications, such as automotive sealing systemsand roofing for buildings. Therefore, the study of the reaction mechanism of graftcopolymerization of polyolefin elastomers/vinyl monomers can not only help us understandthe reaction process of graft copolymerization and the structure and properties of the graftcopolymers, but also guide us through the synthesis of the graft copolymers that can bettersatisfy the requirement.
In this thesis, seven graft copolymerization systems, including EPDM/St-AN, EPDM/St,EPDM/MMA, EPM/St-AN, PEB/MMA-AN and IIR/MMA-AN in suspension andEPDM/MMA in solution, were carried out by free radical polymerization at80℃usingbenzoyl peroxide (BPO) as initiator. For each system, a sequential reaction products ofdifferent reaction times were synthesized. After the synthesis, each product was separated bySoxhlet extraction to obtain purified components, which were subsequently characterized byGPC, FTIR and1H-NMR analyses. The monomer conversion rate (CR), average graft ratio(GRa), graft efficiency (GE), grafted monomer conversion rate (CRg), non-grafted monomerconversion rate (CRf), rubber graft ratio (GRr), true graft ratio (GRt) and gel rate (CPR) werecalculated and plotted against the reaction time. The dependence of these reaction behaviors onreaction time was systematically investigated. The results showed that the chain transfer graftreaction (i.e.“graft from” reaction) occurred at the same time as the free polymerizationreaction at the beginning of the synthesis and stopped after about100min, and the reactionrate of the former was significantly higher than that of the latter in all systems exceptIIR/MMA-AN. A “curled-coil” model of suspension particle formed by aggregates ofmonomers, initiators, free radicals and macromolecules of the polyolefin elastomers/vinylmonomers graft copolymerization system was established to explain the above-mentionedreaction behaviors.
Based on the study of the variation of GRawith increasing reaction time and the analysisresult that GRakept rising after the “graft from” reaction stopped, we discovered that therewere still two other potential grafting elementary reactions, which we called the “graft onto”reaction and the “bridge” crosslinking reaction, occurring between the grafted chains of thegraft copolymers and the molecular chains of the free polymers via their reactive side groups.As for EPDM/St-AN and EPDM/MMA in suspension, the “bridge” crosslinking reactionoccurred after the “graft onto” reaction, and both chemical reaction equations of them werederived; however, neither of them but the suspected thermal initiation of St graftpolymerization was found in the EPDM/St suspension system, and in the other systems onlythe “graft onto” reaction was found.
GPC analysis showed that there was a bimodal molecular weight distribution of the freepolymers formed in the early stage of the reaction process, due to the co-existence of twodistinct molecular populations of low and high molecular weights, which were respectivelyformed by chain transfer termination and bi-radical termination of the free polymeric radicals.According to this discovery and the mechanism of the chain transfer graft reaction, we deriveda universal formula M g, n=m g M L, n/(m f r)to estimate the number-average molecularweight of the grafted chains of every system. The results showed that the number-averagemolecular weight of the grafted chains was much larger than that of the free polymers formedby chain transfer termination of the free polymeric radicals, and was generally smaller than thatof the free polymers formed by bi-radical termination of the free polymeric radicals.
Based on the study of the effect of reaction time on GRrand the molecular weight of thegrafted chains, the free polymers and the non-grafted rubber, we discovered that after the “graftfrom” reaction stopped, the chain scission reaction of grafted and non-grafted rubbers occurredin all systems except EPDM/St, followed by the random radical-radical combination of theresultant chain segments to form soluble “multi-block” copolymers, leading to a furthersignificant improvement of GRr. Both chemical reaction equations of them were derived.
The effect of the reaction behaviors on the notched Izod impact strength of the blendsprepared by melt blending of the reaction product and the styrene-acrylonitrile copolymers(SAN resin) was investigated. The results showed that for the same system, GRrplayed adominant role in the toughening effect of the reaction product on the SAN resin; for differentsystems, the reaction product with gel structure formed by “bridge” crosslinking reaction had ahigher toughening effect on the SAN resin. TEM analysis showed that with increasing reactiontime, the domain size of the rubber phase of the blends decreased and the notched Izod impact strength of the blends increased; the dispersed phase of rubber particles which exhibited a“salami” like structure had the highest toughening efficiency on the SAN resin. At the sametime, SEM analysis showed that the toughening mechanism of the blends was high shearyielding with “cold drawing” of the SAN matrix. The co-constitute ratio of the free copolymersand the grafted chains was measured by FTIR and1H-NMR quantitative analyses, respectively,providing experimental proof for analyzing the compatibility of the reaction product and theSAN resin. DMA analysis showed that the graft copolymers in the reaction product couldsignificantly improve the compatibility between the rubber phase and the SAN phase. Meltmass-flow rate (MFR) measurements showed that the MFR of the blends declined withincreasing reaction time.
The effect of the recovery method of the reaction product on the structure and properties ofthe reaction product was also studied. The results showed that the method, which ended thereaction using p-benzoquinone (PBQ) as terminator and dried the reaction product at roomtemperature, could effectively avoid the ensuing side reactions induced by the residual BPO inthe reaction product during the recovery process, and thus ensure the accuracy of the reactionbehaviors in the study of the reaction mechanisms of the graft copolymerization system.However, the method, which ended the reaction without using any terminator and dried thereaction product at80℃for8hours, resulted in a profound change in the structure andproperties of the reaction product.
引文
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