以RAFT活自由基乳化聚合法合成用於不飽和聚酯、乙烯基酯及環氧樹脂之奈米級及次微米級之高分子核殼型添加劑

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研究生：	許毓倫 Yu-Lun Hsu
論文名稱：	以RAFT活自由基乳化聚合法合成用於不飽和聚酯、乙烯基酯及環氧樹脂之奈米級及次微米級之高分子核殼型添加劑 Synthesis of nano-scale and submicron-scale polymeric core-shell rubber additives RAFT living free radical emulsion polymerizations for unsaturated polyester, vinyl ester, and epoxy resins.
指導教授：	黃延吉 Yan-Jyi Huang
口試委員:	陳崇賢 Chorng-Shyan Chern 邱文英 Wen-Yen Chiu
學位類別：	碩士 Master
系所名稱：	工程學院 - 化學工程系 Department of Chemical Engineering
論文出版年：	2011
畢業學年度：	99
語文別：	中文
論文頁數：	340
中文關鍵詞：	RAFT活自由基種子乳化聚合、傳統乳化聚合、核殼型橡膠添加劑、不飽和聚酯、乙烯基酯樹脂、環氧樹脂
外文關鍵詞：	core-shell rubber(CSR), unsaturated polyester resin (UP), epoxy resin (EPR), vinyl ester resin (VER), seeded emulsion polymerizations, reversible addition-fragmentation chain transfer
相關次數：	點閱：308 下載：0
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本文主要探討以乳化聚合法合成具有不同奈米級顆粒大小和不同外殼組成的通用型核殼橡膠(gp-CSR)及以RAFT聚合法(採用自發性相反轉、無界面活性劑乳化聚合法)合成具有不同奈米級顆粒大小的RAFT型特用核殼橡膠(s-CSR)，作為不飽和聚酯樹脂(UP)，環氧樹脂(EPR)和乙烯基酯樹脂(VER)的抗體積收縮劑(LPA)及增韌劑。並且合成兩種不同化學結構之傳統UP，包括MA-PG型、MA-PA-PG型UP，及vinyl ester resin (VER)與環氧樹脂(EPR)，進而設計出具不同相溶性之苯乙烯(St)/UP(或VER)/gp-CSR(或s-CSR)、EPR/DDM(或DDS)/s-CSR三成份系統。通用型核殼橡膠(gp-CSR)先以半批次進料方式聚合丙烯酸正丁酯(BA)，形成PBA軟質核心，再以批次進料方式聚合甲基丙烯酸甲酯(MMA)及丙烯酸甲酯(MA)，分別形成PMMA硬質外殼與PMA軟質外殼，gp-CSR之外殼又添加5 mol%與10 mol%的甲基丙烯酸環丙氧酯(Glycidyl methacrylate, GMA)共單體及交聯劑(EGDMA)進行改質，以合成出具高極性及具特殊官能基基團外殼之gp-CSR，以增加CSR外殼之極性與樹脂基材化學交聯之能力。利用Debye’s eq.及基團貢獻法，計算出UP、EPR、VER與CSR之外殼的偶極矩，以解釋St/UP(或VER)/gp-CSR(或s-CSR)、EPR/DDM(或DDS)/s-CSR三成份系在25℃(St/VER/gp-CSR or s-CSR)及80℃(EPR/DDM/gp-CSR or s-CSR)及95℃(EPR/DDS/gp-CSR or s-CSR) 及110℃(St/VER/gp-CSR or s-CSR)下未反應前之相溶性。再利用掃描式電子顯微鏡(SEM)來觀測St/VER/gp-CSR或EPR/DDM/gp-CSR三成份系統於110℃下聚合固化後樣品被破壞的微觀形態，來了解CSR顆粒大小及化學組成對三成份系統固化過程中之相溶性影響。

Synthesis of acrylic type of core-shell rubbers (gp-CSR) with varied nano-scale and submicron-scale particle size and shell chemical composition. And synthesis of s-CSR by RAFT polymerization via spontaneous phase inversion process and RAFT surfactant-free, batch emulsion polymerization as low-profile additives (LPA) and tougheners for unsaturated polyester resins (UP) ,epoxy resin (EPR) and vinyl ester resin (VER) have been investigated. Two types of conventional nsaturated polyester resin with different chemical structures, namely, MA-PG type of UP and, MA-PA-PG type of UP, epoxy resin (EPR) and vinyl ester resin (VER) ,have also been synthesized so that styrene (St) /UP(or VER) /CSR or EPR/DDM/CSR ternary systems with different miscibility can be designed.
In the synthesis of the core-shell rubber, a semi-batch process was used to synthesize the soft core, which was made from poly(butyl acrylate) (PBA) , whereas a batch process was to employed to synthesize the hard shell , which was composed of poly(methyl crylate) (PMA) . Also, the shell of the gp-CSR was modified with a crosslinking agent, ethylene glycol dimethacrylate (EGDMA). In addition, the shell of gp-CSR has also been modified by introducing glycidyl methacrylate(GMA) as a comonomer to both decrease the molecular polarity and provide the specific functionality for the shell of the CSR.
By using Debye’s equation and the group contribution method, the dipole moments of UP、VER、EPR and the shell component of the CSR can be calculated, which can then explain the phase characteristics of the St/UP(或VER)/gp-CSR(或s-CSR)、EPR/DDM(或DDS)/s-CSR ternary system prior to the reaction at 25℃(St／UP(或VER)／s-CSR)、80℃(EPR/DDM/s-CSR) 、95℃(EPR/DDS/s-CSR) and 110℃(St／VER／gp-CSR).

摘要................................................................................................................................ I
ABSTRACT ............................................................................................................... III
目錄............................................................................................................................... V
圖目錄......................................................................................................................... IX
表目錄........................................................................................................................ XV
第一章 緒論 ............................................................................................................... 1
1-1 簡介 .............................................................................................................................................. 1
1-2 不飽和聚酯(UP)之合成 ............................................................................................................... 5
1-3 環氧樹脂(EPR)之合成 ................................................................................................................ 6
1-4 乙烯基酯樹脂(VER)之合成 ........................................................................................................ 7
1-5 不飽和聚酯樹脂（UP）與苯乙烯（ST）之交聯共聚合反應 .................................................. 8
1-6 種子乳化聚合反應與複合乳膠顆粒的應用及製備 ................................................................. 13
1-7 RAFT聚合法合成無乳化劑自由基乳化聚合反應之特用型核殼橡膠 ................................... 14
1-8 苯乙烯(ST) /不飽和聚酯(UP) /抗收縮劑(LPA)三成份系統之相容性 ..................................... 15
1-9 研究範疇 .................................................................................................................................... 16
第二章 文獻回顧 ....................................................................................................... 18
2-1 不飽和聚酯（UP）之合成 ....................................................................................................... 18
2-2 環氧樹脂(EPOXY RESIN，EPR)之合成 ...................................................................................... 20
2-3 乙烯基酯樹脂(VINYL ESTER RESIN，VER) 之合成 ................................................................ 21
2-4 乳化聚合法 ................................................................................................................................ 26
2-5 自由基聚合反應 ........................................................................................................................ 34
2-6 無乳化劑之乳化聚合反應與機構 ............................................................................................. 37
2-7 活性自由基聚合法 .................................................................................................................... 40
2-8 原子轉移自由基聚合法(ATRP) ................................................................................................ 42
2-9 穩定自由基聚合法(SFRP)......................................................................................................... 44
2-10 可逆加成-斷裂鏈轉移聚合法(RAFT) .................................................................................... 46
2-11 乳液的安定性........................................................................................................................... 49
2-12 共聚合反應機構與控制共聚合體組成 ................................................................................... 54
2-13 苯乙烯（ST）／不飽和聚酯（UP）／抗收縮劑（LPA）三成份系之相溶性 .................. 58
2-14 ST／UP(或VER)／核殼型橡膠(CSR)三成份系之相溶性..................................................... 60
第三章 實驗方法及設備 ......................................................................................... 61
3-1原料 ............................................................................................................................................. 61
3-1-1不飽和聚酯樹脂的合成原料 ............................................................................................. 61
3-1-2 環氧樹脂與乙烯基酯樹脂的合成原料 ............................................................................ 63
3-1-2奈米級通用型核殼型橡膠之合成原料 ............................................................................. 65
3-1-4 RAFT聚合法之鏈轉移詴劑DBTTC(dibenzyltrithiocarbonate)之合成原料 ................ 68
3-1-5以RAFT聚合法合成之特用型核殼型橡膠s-CSR之合成原料 ..................................... 69
3-2實驗儀器 ..................................................................................................................................... 71
3-2-1 UP之合成及鑑定設備 ....................................................................................................... 71
3-2-2 Epoxy之合成設備.............................................................................................................. 73
3-2-3 VER之合成設備 ................................................................................................................ 75
3-2-4 通用型核殼橡膠之合成設備 ............................................................................................ 77
3-2-5 RAFT聚合法合成特用型核殼型橡膠s-CSR之合成設備 ......................................... 79
3-3 實驗步驟 ................................................................................................................................... 81
3-3-1 不飽和聚酯(UP)之合成 .................................................................................................... 81
3-3-2 UP分子量之測定-末端基滴定法 ..................................................................................... 85
3-3-3 EPR(Epoxy Resin)環氧樹脂之合成 ................................................................................... 88
3-3-4 環氧樹脂之環氧當量測定 ................................................................................................ 90
3-3-5乙烯基酯樹脂之合成 ......................................................................................................... 92
3-3-6 VER中未反應酸含量之測定－末端基滴定法 ................................................................ 94
3-3-7 VER中未反應環氧基團含量之測定－末端基滴定法 .................................................... 96
3-3-8 奈米級核殼型橡膠之合成 ................................................................................................ 97
3-3-9 RAFT聚合法之鏈轉移詴DBTTC(dibenzyltrithiocarbonate) ........................................ 104
之合成 ........................................................................................................................................ 104
3-3-10無界面活性劑乳化聚合(Surfactant-Free Emulsion Polymerization)之合成步驟[33,52,97] ................................................................................................................................. 105
3-3-10-1 E1型無界面活性劑乳液之製備 ........................................................................................... 105
3-3-10-2 E2型活高分子之製備............................................................................................................ 105
3-3-10-3 E3型活高分子之製備............................................................................................................ 105
3-3-11總體RAFT共聚合/自發性相反轉Spontaneous Phase Inversion [33,97] .................... 107
3-3-11-1 E4型活高分子之製備 ........................................................................................................... 107
3-3-11-2 E5-5 (Dn=5nm) 型活高分子之製備 ...................................................................................... 108
3-3-11-3 E5-13 (Dn=13nm) 型活高分子之製備 .................................................................................. 109
3-3-12利用自發相反轉程序之無界面活性劑種子乳化聚合 (Emulsifier-free RAFT seeded emulsion polymerizations with spontaneous phase inversion processes):[33,97]....................... 111
3-3-12-1 E6-28 (Dn=28nm) 型活高分子之製備 .................................................................................. 111
3-3-12-2 E6-100 (Dn=100nm) 型活高分子之製備 .............................................................................. 111
3-3-12-3 E7-100 (Dn=100nm) 型核殼型活高分子之製備 .................................................................. 112
3-3-12-4 E7-15 (Dn=15nm) 型核殼型活高分子之製備 ...................................................................... 112
3-3-12-5 E7-60 (Dn=60nm) 型核殼型活高分子之製備 ...................................................................... 112
3-3-13 單體的純化[98] ............................................................................................................. 114
3-3-14轉化率的測定[52,88] ..................................................................................................... 115
3-3-15 乳液粒徑的測定[52,88] ................................................................................................ 116
3-3-16 CSR粉末的製備 ............................................................................................................ 117
3-3-16-1 通用型核殼型橡膠gp-CSR粉末的製備 ............................................................................. 117
3-3-16-2 特用型核殼型橡膠s-CSR粉末的製備 ................................................................................ 118
3-3-17相對分子量及分子量分佈之測定 ................................................................................. 118
3-3-17-2 樣品相對分子量及分子量分布之測定 ................................................................................ 118
3-3-18 核磁共振光譜之測定 .................................................................................................... 119
3-3-19 玻璃轉移溫度(Tg)[29] ................................................................................................... 120
3-3-20 相分離之測定分析[88] ................................................................................................. 120
3-3-20-1 gp-CSR相分離之測定: .......................................................................................................... 120
3-3-20-2 s-CSR相分離之測定: ............................................................................................................ 122
第四章 結果與討論 ................................................................................................. 124
4-1 MA-PG型及MA-PA-PG型之UP樹脂 ................................................................................. 124
4-1-1 MA-PG型及MA-PA-PG型之UP樹脂的合成 ............................................................. 124
4-1-2 MA-PG型及MA-PA-PG型UP樹脂之副反應 ............................................................. 129
4-1-3 MA-PG型及MA-PA-PG型之UP樹脂的鑑定分析 ..................................................... 130
4-2 環氧樹脂 .................................................................................................................................. 142
4-2-1環氧樹脂的合成 ............................................................................................................... 142
4-2-2環氧樹脂的鑑定分析 ....................................................................................................... 143
4-3乙烯基酯樹脂 ........................................................................................................................... 150
4-3-1乙烯基酯樹脂(VER)之合成 ............................................................................................ 150
4-3-2乙烯基酯樹脂(VER)之鑑定分析 .................................................................................... 152
4-4 合成樹脂時注意事項 ............................................................................................................. 158
4-4-1合成MA-PG型及MA-PA-PG型UP時注意事項 ........................................................ 158
4-4-2合成環氧樹脂時注意事項 ............................................................................................... 160
4-4-3合成乙烯基酯樹脂(VER)時注意事項............................................................................. 161
4-4 GPC檢量線之繪製 .................................................................................................................. 162
4-5 通用型奈米級核-殼型橡膠增韌劑(GP-CSR)之合成[43] ....................................................... 163
4-6 通用型奈米級核-殼型橡膠增韌劑(GP-CSR)之NMR分析[43,87,88] .................................. 184
4-7奈米級GP-CSR之玻璃轉移溫度(TG) [43, 52] ......................................................................... 197
4-8 利用TEM觀測通用型核殼型橡膠GP-CSR乳液 ................................................................. 212
4-9 合成GP-CSR時注意事項........................................................................................................ 232
4-10 RAFT聚合法之鏈轉移詴劑DBTTC之鑑定分析 ............................................................... 233
4-11以RAFT聚合法合成之S-CSR之鑑定分析 ......................................................................... 238
4-12 ST/UP(或VER)/GP-CSR(或S-CSR)及EPR/DDM(或DDS) /GP-CSR(或S-CSR)三成份系之相溶性 ................................................................................................................................................. 275
4-12-1 樹脂與gp-CSR、s-CSR外殼之分子極性 ................................................................... 275
VIII
4-12-2 EPR以基團貢獻法計算其偶極矩: ................................................................................ 279
4-12-3 VER以基團貢獻法計算其偶極矩: ............................................................................... 284
4-12-4 MMA-G1、MMA-G2、MMA-G3型gp-CSR以基團貢獻法計算其偶極矩: ............ 286
4-12-5 MA-G1、MA-G2、MA-G3型gp-CSR以基團貢獻法計算其偶極矩: ....................... 290
4-12-6 E7-15型s-CSR以基團貢獻法計算其偶極矩 .............................................................. 294
4-13 PHASE CHARACTERISTICS ........................................................................................................ 306
第五章 結論 ............................................................................................................. 311
第六章 建議與未來工作 ......................................................................................... 313
第七章 參考文獻 ..................................................................................................... 314
第八章 附錄 ............................................................................................................. 322

                                

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