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可逆的架橋が可能な有機・無機ハイブリッド 高分子 …...1 神奈川大学...
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1 神奈川大学 大学院工学研究科 応用化学専攻 教授 亀山 敦 可逆的架橋が可能な有機・無機ハイブリッド 高分子材料 2017年12月5日
Transcript of 可逆的架橋が可能な有機・無機ハイブリッド 高分子 …...1 神奈川大学...
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神奈川大学 大学院工学研究科
応用化学専攻
教授 亀山 敦
可逆的架橋が可能な有機・無機ハイブリッド
高分子材料
2017年12月5日
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研究分野の背景
・自動車のEVシフトが加速
⇒ パワーエレクトロニクスデバイス
の小型化が急務
⇒例えば、インバーター高温実装
⇒ 耐熱性、実装プロセス低コスト化
を両立できる封止材、さらに、リ
サイクル性を実現できる封止材
が求められている。
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研究分野の背景 有機・無機ハイブリッド高分子材料の合成法 １．物理的な混合
Toyota Process, 1993
課題： ナノフィラーの 凝集を抑制した 均一分散
２．化学的手法（ゾル-ゲル法）によるハイブリッド化
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研究分野の背景 無機ナノフィラーとしてのPOSS
R: 有機置換基（相溶性向上、 反応性基の場合 ⇒ 混合後に化学反応で主剤に固定化）
POSS: かご型シルセスキオキサン
d=1~3 nm
Advantege: a) High chemical stability b) Mechanical strength c) High thermal stability
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
OR
R
R R
R
R
RR
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
OR
R R
R
R
R
RR
NH
OO
O
NNMe Bu
R =
Y. Chujo et al., J. Am. Chem. Soc. 2010, 132, 17649-17651. Y. Chujo et al., Polym. J. 2011, 43, 708-713.
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
ON COOH
NN
N
N
NN
N
COOH
COOH
HOOCCOOHHOOC
HOOC
HOOC
HOOC
HOOC
HOOC
HOOC HOOC COOH
HOOCCOOH
K. Naka et al., Langmuir 2007, 23, 9057-9063.
報告例
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従来技術とその問題点 ２．化学的手法によるハイブリッドエポキシ樹脂
1) ゾル-ゲル法によるシリカハイブリッドエポキシ樹脂
2) POSS類似エポキシモノマーを添加したハイブリッドエポキシ樹脂
越智光一、ネットワークポリマー、32(5), 245-249 (2011).
・耐熱性、強度が向上したハイブリッドエポキシ樹脂が得られるが、
脆性が問題。
POSS類似エポキシモノマー
+ エポキシ樹脂 ハイブリッド エポキシ樹脂
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新技術
☆ 優れた耐熱性と靱性を有する
シリカハイブリッド高分子材料
☆ 実装性
☆ リサイクル性の実現
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R:
B. Seurer, E. B. Coughlin, Macromol. Chem. Phys. 2008, 209, 2040-2048 L. Zheng et al., Macromolecules 2004, 37, 8606-8611.
有機・無機ハイブリッド高分子材料の新しい合成法 ３．高分子の分子設計
Si
Si
Si
SiSi
Si
SiSi
O
O
O
O
O
O
O O
O
O
OO
R
RR
R
R
R
R
r Bm n
A
R: Phenyl
無機フィラー成分であるPOSSを共有結合で
高分子の側鎖に導入
＊POSSの分散状態の制御が容易
＊有機成分と無機成分の結合が強固
＊共重合体の化学構造の制御により、
耐熱性と靱性の両立が可能
報告例（従来技術）
課題： ・いずれの例でも、エラストマーの 特性向上を目的としている。 ・高分子の化学構造について、 汎用性が低い。
新技術の特長・従来技術との比較
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Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
F
BuNBuBu
Bu
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O On
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架橋したハイブリッド高分子
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
RR
架橋
可溶性高分子
新技術
Si
Si
Si
SiSi
Si
SiSi
O
O
O
O
O
O
O O
O
O
OO
R
RR
R
R
R
R
r Bm n
A
解架橋
可逆的架橋が可能な有機・無機ハイブリッド高分子材料
リサイクル
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Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
側鎖にPOSS部分を有するポリメタクリル酸エステル誘導体 －特 徴－
＊汎用性の高い化学構造、合成が容易
＊高耐熱性、高透明性
＊多様な化学構造を持つ高分子の合成が可能
⇒ 強度と靱性を両立することが可能
＊可逆的な架橋の実現
なぜ、可逆的架橋ができるのか？
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
OTBAF
F
SiHO
OHHO
SiSi
Si
Si
Si
Si
SiO
OO
O
OH
OHOO
OO O
OH
BuNBuBu
Bu
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
FBuNBuBu
Bu
H2O -H2O
Chem. Mater. 2008, 20, 4299-4309.
新技術
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Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
F
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
NBu4
Si
Si
Si
Si
Si
Si
SiO
O
HOHO
O
OOO
OHO O
O
O O
Bu4NF
SiHO OH
OH NBu4
F
Si OHOH
ROH
Si OHOH
ROH
SiOH
HOOH
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
R
O On
新技術 可逆的架橋システム
(TBAF)
高分子の 架橋・解架橋
動的なPOSSの組換え反応を基盤とした可逆的架橋の反応様式
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Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
F
BuNBuBu
Bu
SiOEt
EtOOEt
TBAF
excess
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O On
THFr.t., 24 h
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PMAPhPOSS Mn 10000, PDI 1.31
POSS部分が架橋した高分子
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O O
n
RR
TBAF 架橋剤
可溶性高分子
可逆的架橋反応
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PMAPhPOSS +
TBAF +
cross-linker
in THF
8
濃縮
代表的な実験結果
200 400 600 8000
10
20
30
40
50
60
70
80
90
100
Tra
nsm
itta
nce /
%
Wavelength / nm
0 200 400 6000
20
40
60
80
100
weig
ht
resi
due (%)
Temperature (oC)
PMAPhPOSS as-made washed with THF washed with acetone washed with methanol washed with ether
優れた透明性 優れた熱安定性
架橋ハイブリッド高分子
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10 15 20
Retention volume (mL)
PMAPhPOSS Mn 10000, PDI 1.31
12
PMAPhPOSS （架橋前）
解架橋された生成物
TMS H2O CHCl3
GPC (THF) 解架橋された生成物 Mn 15000, PDI 1.43
Si
SiSi
Si
Si
Si
Si
SiO
OO
O
O
OOO
OO O
O
O Ox
Si
SiSi
Si
Si
Si SiOOHO
OH
O
OOO
OOOH
O
O O
y
動的解架橋のキャラクタリゼーション
推定構造
Graph1
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