Method for preparing plant oil-based cyclic carbonate prepolymer through thiol-ene click reaction
A cyclocarbonate and vegetable oil-based technology, which is applied in the field of preparation of vegetable oil-based cyclocarbonate prepolymers, can solve the problem of not being able to design and control the number of cyclocarbonate group connections, unfavorable safety production, and reduced reactivity, etc. problem, achieving highly reproducible, method-simple, and highly reactive results
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Embodiment 1
[0019] 1) the preparation method that contains mercapto ring carbonate:
[0020] Add 5.4g of glycerol cyclocarbonate, 5.8g of 3-mercaptopropionic acid, 0.56g of p-toluenesulfonic acid, and 20ml of dichloromethane into the reaction flask in turn, and reflux at 80°C for 8h; wash the solution three times with deionized water , and then dried with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain 3.6 g of mercapto-containing ring carbonate with a yield of 67%.
[0021] 1 H NMR (400MHz, δppm) 4.95 (ddd, J = 9.1, 6.1, 3.8Hz, 1H), 4.58 (t, J = 8.6Hz, 1H), 4.43 (dd, J = 12.6, 3.3Hz, 1H), 4.35 (dd,J=5.2,2.6Hz,1H),4.32(d,J=5.3Hz,1H),2.81(td,J=7.9,4.0Hz,2H),2.74(dd,J=10.2,3.9Hz, 2H),1.71–1.61(m,1H).
[0022] 13 C NMR (100MHz, CDCl 3, δppm) 171.18(OC=O), 154.56(OC(O)O), 73.82(CH), 65.19(CH 2 ), 63.24 (CH 2 ), 38.09 (CH 2 ), 19.45 (CH 2 ).
[0023] FTIR(KBr)ν:2954,2571(SH),1794(OC(O)O),1740(OC=O),1400,1097,1057,772,708cm -1 .
[0024] 2) T...
Embodiment 2
[0046] The mercapto-containing ring carbonate that 1.36g embodiment 1 makes, 1.9g castor oil, 0.097g 2-hydroxyl-2-methyl-1-phenylacetone, 3ml trichloromethane are added in reaction flask successively, at 2.0 mw / cm 2 Under ultraviolet light irradiation, react at 35° C. for 10 h; remove the solvent to obtain a castor oil-based cyclocarbonate prepolymer with an average functional group number of cyclocarbonate of 2.9, and the yield is 100%.
[0047] 1 H NMR (400MHz, CDCl 3,δppm) 5.27(d, J=20.4Hz, 1H), 4.96(s, 3H), 4.57(t, J=8.4Hz, 3H), 4.50–4.23(m, 10H), 4.14(dd, J=11.8, 5.9Hz, 3H), 3.68(dt, J=47.9, 23.9Hz, 3H), 3.05–2.47(m, 20H), 2.44–2.22(m, 6H), 1.84–1.05(m, 77H), 0.87(d ,J=6.7Hz,9H).
[0048] 13 C NMR (100MHz, CDCl 3, δppm) 173.17(OC=O), 171.32(OC=O), 154.25(OC(O)O), 73.70(CH), 71.86(CH), 68.91(CH), 65.96(CH 2 ), 63.19 (CH 2 ),62.05(CH 2 ), 46.15 (CH 2 ), 37.76 (CH 2 ),37.56(CH 2 ), 34.33 (CH 2 ), 33.89–33.20 (CH 2 ), 32.68–32.60 (CH 2 ), 30.53 (CH 2 ), 26.80–...
Embodiment 3
[0050] Add 1.48g of the mercapto-containing ring carbonate prepared in Example 1, 1.9g of olive oil, 0.1g of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, and 3ml of chloroform into the reaction flask at 1.4mw / cm 2 Under ultraviolet light irradiation, react at 30° C. for 16 h; remove the solvent to obtain an olive oil-based cyclocarbonate prepolymer with an average functional group number of 3 cyclocarbonates, and the yield is 100%.
[0051] 1 H NMR (400MHz, CDCl 3, δppm)5.25(s,1H),4.95(s,3H),4.58(td,J=8.6,3.5Hz,3H),4.35(ddt,J=21.6,19.0,9.2Hz,10H),4.14(dd, J=11.8, 5.7Hz, 2H), 3.03–2.47(m, 15H), 2.33(dd, J=20.7, 13.6Hz, 6H), 1.77–1.11(m, 75H), 0.87(t, J=6.5Hz ,9H).
[0052] 13 C NMR (100MHz, CDCl 3, δppm) 173.14(OC=O), 171.48(OC=O), 154.25(OC(O)O), 73.64(CH), 68.90(CH), 66.03(CH 2 ), 63.14 (CH 2 ), 62.08 (CH 2 ), 58.46(CH), 46.39(CH 2 ),37.77(CH 2 ),34.75(CH 2 ), 33.87 (CH 2 ), 3.89 (CH 2 ), 29.79-29.383 (CH 2 ), 29.21 (CH 2 ), 26.8078 (CH 2 ),25.15(CH 2 ),2...
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