Cyclopolymer containing carbamido large ring and production method and application thereof

A polymer and urea-based technology, applied in the field of cyclized polymers containing urea-based macrocycles and their preparation, can solve problems such as limiting polymer yields, overcome low polymerization yields, high reaction yields, and achieve achievable The effect of controlled change

Active Publication Date: 2019-07-09
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, low concentrations of reactants often limit the yield of polymers [Gokel G.W., Leevy W.M. and Weber M.E. Chem. Rev., 2004, 104, 2723-2750]

Method used

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  • Cyclopolymer containing carbamido large ring and production method and application thereof
  • Cyclopolymer containing carbamido large ring and production method and application thereof
  • Cyclopolymer containing carbamido large ring and production method and application thereof

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preparation example Construction

[0039] The present invention provides a kind of preparation method of the cyclic polymer containing ureido macrocycle, comprising:

[0040]A monomer, a chain transfer agent, an initiator and a solvent are mixed and reacted to obtain a ureido-containing macrocyclic cyclic polymer having a structure of formula (II);

[0041] Wherein, the monomer has a structure shown in formula (I),

[0042]

[0043] where the R 1 is hydrogen or C1-C10 alkyl;

[0044] The R 2 is hydrogen or C1-C10 alkyl;

[0045] The X is a C2-C10 straight-chain alkylene group, a C3-C8 cycloalkyl group, a C3-C30 cycloalkyl-containing alkylene group, a C6-C20 arylene group, a C8-C30 aromatic hydrocarbon group-containing Hydrocarbylene or C2-C20 hydrocarbon containing ether group;

[0046] m is 10-100.

[0047] According to the present invention, the present invention mixes and reacts monomers, chain transfer agents, initiators and solvents to obtain cyclized polymers containing ureido macrocycles; wherei...

Embodiment 1

[0081] Monomer: 1,2-bis(acryloyloxyethylurea)cyclohexane (formula I-X-1), in the general formula of bifunctional monomer M, X is ortho-cyclohexyl, R 1 , R 2 for hydrogen. The synthesis steps are as follows:

[0082] Weigh 11.40 g (0.10 mol) of 1,2-cyclohexanediamine, dissolve it in 150 mL of dry dichloromethane, and add acryloyloxyethyl isocyanate (0.20 mol) in dichloromethane dropwise at room temperature under nitrogen protection. Solution 150mL. After the dropwise addition was completed, stirring was continued for 3 hours to obtain a white solid. Suction filtration, washing with dichloromethane three times (30mL×3), and vacuum drying gave 34.10g of 1,2-bis(acryloyloxyethylurea)cyclohexane, m.p.>280°C, yield 86.0%.

[0083] 1 H NMR (400MHz, DMSO, δin ppm): 1.02-1.17 (4H, -CH 2 (CH 2 ) 2 CH 2 -), 1.53-1.55 (2H, -CH 2 (CH2) 2 CH 2 -), 1.79-1.82 (2H, -CH 2 (CH 2 ) 2 CH 2 -), 3.18-3.22 (4H, -COOCH 2 CH 2NH-), 3.95-4.05 (4H, -COOCH 2 CH 2 NH-), 5.81-5.83 (2H, -...

Embodiment 2

[0086] Monomer: 1,3-bis(acryloyloxyethylurea) benzene (formula I-X-5), in the general formula of bifunctional monomer M, X is meta-phenyl, R 1 , R 2 for hydrogen, R 3 for hydrogen. The synthesis steps are as follows:

[0087] Weigh 10.80 g (0.10 mol) of 1,3-phenylenediamine, dissolve it in 150 mL of dry dichloromethane, and add acryloyloxyethyl isocyanate (0.20 mol) in dichloromethane dropwise at 30°C under nitrogen protection. Solution 150mL. After the dropwise addition was completed, stirring was continued at this temperature for 10 hours to obtain a white solid. Suction filtration, washing with dichloromethane three times (30mL×3), and vacuum drying gave 37.20g of 1,3-bis(acryloyloxyethylurea)benzene, m.p.=180-181°C, yield 95.4%.

[0088] 1 H NMR (400MHz, DMSO, δin ppm): 3.30-3.34 (4H, -COOCH2CH2NH-), 4.09-4.12 (4H, -COOCH2CH2NH-), 5.92-5.94 (2H, -CONHPh), 6.12-6.14 (2H, - CH2NHCO), 6.16-6.35 (6H, CH2=CH-), 6.92-7.02 (2H, Ph), 7.40-7.43 (1H, Ph), 8.48 (1H, Ph).

[0...

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Abstract

The invention provides a cyclopolymer containing a carbamido large ring and a production method and application thereof. The production method comprises the step of mixing monomer, a chain transfer agent, an initiator and a solvent for reaction to obtain the cyclopolymer containing the carbamido large ring; and by choosing the specific monomer for large ring production, the problem that in ordinary bifunctional monomer, due to low intramolecular bifunctional reactive activity, synthesis of large ring cyclopolymer is difficult is solved. The monomer can be subjected to cyclization reaction whenthe concentration is lower than 0.3 mol/L, and the reaction yield is high, so that the problems that under a low concentration condition, the polymerization yield is low, and under a high concentration condition, cross-linking is liable to happen during polymerization are solved. Moreover, by changing the length of an X group chain, controllable change of the size of the large ring can be achieved.

Description

technical field [0001] The invention relates to the field of macromolecular polymers, in particular to a cyclized polymer containing ureido macrocycles, a preparation method and application thereof. Background technique [0002] Macrocyclic polymers usually refer to macromolecules with 12 or more covalent atoms combined to form rings. Designing and synthesizing macrocyclic polymers has always been an important field of research for chemists [Aviles-Moreno J.R., Quesada-Moreno M.M., Lopez-Gonzalez J.J.et al.J.Phys.Chem.B, 2013, 117(32):9362-9370; Cheng C., CaiZ.W., Peng X.S., et al.J.Org.Chem., 2013, 78(17):8562-8573]. Cyclopolymers containing macrocycles are a class of polymers obtained by intramolecular and intermolecular alternate chain growth of bifunctional monomers [Sakai, R., Satoh, T., Kakuchi, R., et al. al. Macromolecules, 2004, 37, 3996-4003]. The macrocycles in this type of polymer can be recognized as metal ions, small organic molecules, chiral molecules, etc....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F122/22C08F2/38C02F1/28C02F101/20
CPCC02F1/285C02F2101/20C08F2/38C08F122/22
Inventor 孙允凯王小峰王梦蝶周文文
Owner NANHUA UNIV
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