Amphiphilic block polymers prepared by olefin metathesis
A polyolefin, multi-block technology, applied in the field of ester functionalization, can solve the problems of by-products and reactants and energy waste
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[0113] Preparation method of functionalized multi-block polyolefin
[0114] The present invention relates to a process for the preparation of functionalized multiblock polyolefins comprising combining an olefin metathesis catalyst with an acrylate or methacrylate functionalized polyalkylene glycol, and one or more vinyl terminated polyolefins ( oligomer or polymer), preferably a vinyl terminated polyolefin contact comprising one or more of the vinyl terminated polyolefins described herein.
[0115] The reactants are usually combined in a reaction vessel at a temperature of 20°C-200°C (preferably 50°C-160°C, preferably 60°C-140°C) and a pressure of 0-1000 MPa (preferably 0.5-500 MPa, preferably 1-250 MPa) Residence time of 0.5 seconds to 10 hours (preferably 1 second to 5 hours, preferably 1 minute to 1 hour).
[0116] Typically, about 0.4 to about 4.0 (eg, 0.5 to 2.6), preferably about 1.0 to about 2.0, most preferably about 1.1 to about 1.7 moles of the acrylate or methacryl...
Embodiment 1
[0617] Embodiment 1: the synthesis of PE-PEG-PE triblock
[0618] 1-Eicosene (1.08 g, 3.84 mmol), poly(ethylene glycol) diacrylate (1.59 g, 2.05 mmol) with an estimated Mn of 777 g / mol, and Zhan1B (0.0175 g, 0.0239 mmol) combined. Then, pentane (4 mL) and dichloromethane (4 mL) were added to form a homogeneous mixture which was heated on a metal block maintained at 45°C. Additional pentane was added periodically as the mixture evaporated over several hours. Keep the mixture at 39 °C overnight. at this time, 1 The HNMR spectrum indicated that 94% of the acrylate groups had undergone cross-metathesis with eicosene with loss of ethylene. The reaction was quenched by adding a few drops of ethyl vinyl ether. Pentane (100 mL) was added and the mixture was passed slowly down a column of neutral alumina with some loss of product that precipitated on the column. The volatiles were removed under vacuum to afford the product as a white solid. Yield: 1.2 g. 1 HNMR (250MHz, CDCl 3...
Embodiment 2
[0621] Embodiment 2: the synthesis of PE-PEG diblock
[0622] 1-Eicosene (2.38 g, 8.48 mmol) and poly(ethylene glycol) methyl ether acrylate (4.47 g, 8.48 mmol) with an estimated Mn of 527 g / mol were combined in a vial. Dichloromethane (8 mL) was added followed by solid Zhan1B (0.062 g, 0.0848 mmol) and some pentane (5 mL). The mixture was kept near reflux on a metal block maintained at 39°C. After stirring overnight, a few drops of ethyl vinyl ether were added. After 0.5 h, the volatiles were removed and pentane (100 mL) was added. Pass this mixture slowly over neutral alumina. Removal of volatiles provided the diblock product as a white semi-solid. Yield 2.53 g. 1 HNMR (500MHz, CDCl 3 ):
[0623] δ6.96(dt, 1.0H), 5.81(d, 1.0H), 4.29(m, 2.0H), 3.70(m, 2.0H), 3.62(m, 21.3H), 3.51(m, 1.8H), 3.35(s, 2.7H), 2.16(q, 2.0H), 1.15-1.46(m, 35.8H), 0.85(t, 3.3H).
[0624]
[0625] where n=about 10.
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