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Proparagyl urea analogue monomer and optical rotation spiral polymer and its preparation method

A technology of propargyl urea and polymer, applied in the field of polymer materials, can solve the problems of low catalytic activity and enantioselectivity, restriction, loss of metal complex catalyst, etc.

Inactive Publication Date: 2006-11-22
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The application of such catalysts is currently limited due to the structural uncertainty, low catalytic activity and enantioselectivity of synthetic polymer catalysts, and the loss of metal complex catalysts during reactions and handling.

Method used

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  • Proparagyl urea analogue monomer and optical rotation spiral polymer and its preparation method
  • Proparagyl urea analogue monomer and optical rotation spiral polymer and its preparation method
  • Proparagyl urea analogue monomer and optical rotation spiral polymer and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]R(+)-N-Benzyl-α-methylbenzylamine (7 mL) was added dropwise to an ice-bathed solution of solid phosgene (Triphosgene 4.64 g) in ethyl acetate. After the dropwise addition, the reaction was heated to reflux, and nitrogen gas was introduced to remove the by-product hydrogen chloride at the same time, and the reaction was stopped after 30 hours. Evaporate the organic solvent to obtain carbamoyl chloride. Carbamoyl chloride was dissolved in dichloromethane and added dropwise to the solution of propargylamine in dichloromethane, and reacted for 5 hours. The resulting solution was washed three times successively with 2N hydrochloric acid and saturated sodium bicarbonate solution, 30 ml each time, and then dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporation to obtain a colorless viscous liquid: propargylcarbamide.

[0042] Take the above monomer (0.1 g) and (nbd) Rh + B - (C 6 h 5 ) 4 Catalysts (the ratio of monomer to ...

Embodiment 2

[0045] The difference from Example 1 is that the polymerization temperature is 0°C and the polymerization time is 24h. All the other polymerization steps are the same as in Example 1. The number average molecular weight of the obtained polymer was 7800, and the molecular weight distribution index was 1.81. The specific optical rotation of the polymer is 850°. The peaks of CD and UV-Vis spectra of the obtained polymer reached the maximum at chloroform-40℃, and the minimum at 55℃. The shapes of the two spectra are similar to those of the circular dichroism spectrum and the ultraviolet-visible spectrum in Example 1, respectively, and the peaks are 10% higher than those in Example 1.

Embodiment 3

[0047] The difference from Example 1 is that the polymerization temperature is -15°C and the polymerization time is 24h. The remaining polymerization steps were the same as in Example 1, and the number average molecular weight of the obtained polymer was 6800, and the molecular weight distribution index was 1.62. The specific rotation of the polymer is 880°. The peaks of CD and UV spectra of the obtained polymer reach the maximum at chloroform -30°C and the minimum at 55°C. The shapes of the two spectrograms are similar to the circular dichroic spectrum and the ultraviolet-visible spectrum in Example 1, respectively, and the peaks are 15% higher than those in Example 1.

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Abstract

The invention discloses a propargyl urea monomer in the macromolecular material domain, which is characterized by the following: group R1 and R2 in the structure formula (1) of propargyl urea monomer are the same or different, which are aromatic radical or alkyl; the number average molecular weight of structure formula (2) of propargyl urea monomer is 6800-136600 and the molecular weight distribution index is 1.34-2.91 with 100 percent sym-form structure. The making method comprises the following steps: adding secondary amine drip at 3:1 rate in the organic solution of solid phosgene; heating to reflux for 10-30h; cooling; removing organic solvent through boiling to produce carbamyl chloride; reacting carbamyl chloride and propargyl amine at 1:1 rate for 2-5 h; neutralizing through alkali after acid cleaning; dewater; boiling out carrene to produce propargyl urea monomer; solving propargyl urea monomer and transition metal accelerant at 50:1-100:1 rate in the organic solvent protected by nitrogen; blending two solutions to polymerize for 2-24 h at -15-30 deg.c; adding skellysolve B; settling; filtering; drying in the vacuum. The invention can produce polymerization with more ideal molecular weight and molecular weight distribution, which can be used in optical, biological and medicine domain.

Description

technical field [0001] The invention belongs to the field of polymer materials. The present invention relates to specific substitution of acetylene monomers and macromolecules as propargylureas. Such polymers can exhibit stable helical conformation and optical rotation under certain external conditions. Background technique [0002] Some biomacromolecules, such as proteins, DNA, etc., can form a stable helical conformation; chemists have begun to study and imitate the chain structure of biomacromolecules. In 1955, Natta successfully prepared isotactic polypropylene, which is It is the beginning of the field of synthetic helical macromolecules. In 1960, Pino recognized the superhelical helical structure of vinyl polymers in solvents through isotactic poly(3-methyl-1-pentene). Although chiral side groups generally affect the helical conformation of polyolefins, poly(benzyl isobutyrate), synthesized by Okamoto and Yuki in 1979, does not require chiral side groups to form a h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F138/00C08F4/22
Inventor 邓建平杨万泰赵伟国王剑敏张志刚
Owner BEIJING UNIV OF CHEM TECH
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