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Preparation method of cyclolefin copolymer

A technology of styrene and polymerization, applied in the field of cyclic olefin copolymers, which can solve the problems of limited polymer properties, low temperature, and unfavorable industrial production.

Inactive Publication Date: 2009-06-10
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the research on the copolymerization of norbornene and ethylene monomer is relatively extensive, but the research on the copolymerization of norbornene with styrene and methyl methacrylate is relatively few.
The copolymerization of norbornene and styrene monomer is only reported in 5 related documents and patents, and the catalytic system used is mainly simple nickel stearate, nickel acetylacetonate, and bridged α-diimide nickel. Catalyst system, in addition, there is no report on other catalytic systems; and the research on the copolymerization of norbornene and methyl methacrylate has not yet been reported
In addition, the catalytic system used in the copolymerization of cycloolefins is simple, so the amount of catalyst used in the polymerization is relatively large, and the temperature during the copolymerization is too low, which is not conducive to industrial production, and the performance of the polymer is limited.

Method used

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  • Preparation method of cyclolefin copolymer
  • Preparation method of cyclolefin copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the synthesis of salicylaldimine nickel compound 1

[0018] Ligand L 1 Synthesis:

[0019] Add 3mL (28mmol) of salicylaldehyde and 3.86g (28mmol) of p-nitroaniline to 80mL of absolute ethanol, and dropwise add 0.5mL of formic acid to reflux reaction for five hours, stop heating, and place the reaction bottle in the refrigerator overnight, with an orange-red solid Precipitated, filtered and dried to obtain 6.3 g of orange-red powder with a yield of 93%. Then recrystallize from a mixture of ethanol and tetrahydrofuran to obtain orange-red crystals. Elemental analysis measured value (%): N, 11.75; C, 64.91; H, 4.11; theoretical value (%): N, 11.55; C, 64.45; H, 4.13; 1 HNMR: (300MHZ, CDCl 3 , δ): 12.55 (s, 1H), 8.63 (s, 1H), 8.31 (d, 2H), 7.44 (m, 4H), 7.00 (m, 2H).

[0020] Synthesis of compound 1:

[0021] Vacuumize the 100mL flask with a branch pipe and fill it with nitrogen, feed nickel acetate hexahydrate, salicylaldehyde, and the corresponding p-n...

Embodiment 2

[0022] Embodiment 2: the synthesis of salicylaldimine nickel compound 2

[0023] Ligand L 2 Synthesis:

[0024] According to the ligand L in Example 1 1 3mL (28mmol) salicylaldehyde and 3.45g (28mmol) p-methoxyaniline were added to 80mL absolute ethanol, and 0.5mL formic acid was added dropwise for reflux reaction for five hours, heating was stopped, and the reaction bottle was placed in the refrigerator overnight , a yellow-green solid was precipitated, which was filtered and dried to obtain 5.8 g of a solid, with a yield of 91%. Then recrystallize with ethanol to obtain yellow-green scale-like crystals. Elemental analysis measured value (%): N, 6.11; C, 73.65; H, 5.69; theoretical value (%): N, 6.15; C, 73.91; H, 5.71; 1 HNMR: (300MHZ, CDCl 3 , δ): 13.44 (s, 1H), 8.593 (s, 1H), 7.367 (d, 2H), 7.273 (d, 2H), 6.90-7.1 (m, 4H), 3.844 (s, 3H).

[0025] Synthesis of compound 2:

[0026] The synthesis method is the same as the preparation of compound 1. Equimolar p-methoxya...

Embodiment 3

[0027] Embodiment 3: the synthesis of salicylaldimine nickel compound 3

[0028] Ligand L 3 Synthesis:

[0029] Add 125g (0.61mol) of 2,4-di-tert-butylphenol, 170g (1.21mol) of hexamethylenetetramine, and 300mL of glacial acetic acid into a 2L three-necked round-bottomed flask, stir magnetically, and within one hour Slowly raise the temperature to 130°C, keep the temperature for 2 hours, cool to 75°C and add 300mL of 33% (W / W) H 2 SO 4 Aqueous solution, under magnetic stirring, the solution is heated to 105°C and refluxed for 1 hour, the stirring and heating are stopped, and then cooled to 75°C, and the reaction mixture is transferred to a separating funnel at a constant temperature, and the organic phase is separated and transferred to 1L In the reaction bottle, after cooling to 50°C, 100 mL of methanol was added, and the mixture was cooled in a refrigerator. A light yellow solid precipitated out. After vacuum filtration, the obtained solid was recrystallized in methanol t...

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Abstract

The present invention discloses process of preparing cycloolefine copolymer. The present invention synthesizes norbornene copolymer material with different monomer contents through polymerization of styrene or methyl methacrylate and norbornene in different monomer material ratios at proper temperature and in the presence of catalyst system comprising salicylal imine-Ni compound, polyaluminoxane and triphenyl phosphine.

Description

technical field [0001] The invention relates to a cycloolefin copolymer, in particular to a preparation method of a cycloolefin copolymer. Background technique [0002] In recent years, scholars at home and abroad have reported that late transition metal catalysts catalyze cyclic olefins (such as norbornene) for vinyl addition polymerization, and the obtained addition polymer polynorbornene has the advantages of high temperature resistance and chemical corrosion resistance. However, because the glass transition temperature of the homopolymer is too high (Tg>360 ℃), it is not conducive to processing, which limits its popularization and application; at the same time, norbornene homopolymer has a certain degree of crystallinity, and the light transmission properties of the polymer not good. Therefore, through the copolymerization of cyclic olefins with ethylene, propylene or other α-olefins, aliphatic chains are introduced into the cyclic olefin polymer chains, which can im...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F4/70C08F2/06C08F220/14C08F212/08
Inventor 林尚安陈晓丽祝方明伍青高海洋
Owner SUN YAT SEN UNIV
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