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Production of irregular phenylethylene/norbornene multipolymer

A norbornene and styrene technology, applied in the chemical industry, can solve the problems of low temperature, limited polymer performance, unfavorable industrial production, etc.

Inactive Publication Date: 2008-11-26
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the catalytic system used is simple, 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 obtained styrene / norbornene copolymer styrene has a relatively low insertion rate. Polymers have limited performance

Method used

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  • Production of irregular phenylethylene/norbornene multipolymer
  • Production of irregular phenylethylene/norbornene multipolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the synthesis of anilino imine nickel compound 1

[0018] Synthesis of Ligand L1:

[0019] 2-fluoro-2,6-dimethylbenzimine (2-F-C 6 h 6 (CH=NC 6 h 3 Synthesis of i-Pr-2, 6)): 11.68g 2-fluorobenzaldehyde and 10.38g 2,6-dimethylaniline were stirred in 40mL n-hexane for 2h, and MgSO was added 4 Dehydration; the obtained bright yellow solution was distilled under reduced pressure, and the fraction at 162-163° C. was collected at 0.5 cmHg to obtain 14.34 g of bright yellow viscous liquid with a yield of 73.7%. Mass Spectrum EI-MS (m / z): 228.2[M] + . Elemental Analysis C 15 h 14 FN: Theoretical: C, 79.22%; H, 6.27%; N, 6.16%. Found values: C, 79.07%; H, 6.21%; N, 6.01%.

[0020] 9.9 mL of butyl lithium (n-BuLi) n-hexane solution (2.6 mol / L) was gradually added to 2,6-dimethylaniline (3.3 mL) in tetrahydrofuran (40 mL) at -78 ° C, and the solution was stirred overnight Slowly rise to room temperature; then dissolve 5.0 mL of 2-fluoro-2,6-dimethylbenzimi...

Embodiment 2

[0023] Embodiment 2: the synthesis of anilino imine nickel compound 2

[0024] Synthesis of Ligand L2:

[0025] According to the synthesis method of ligand L1 in Example 1, 2,6-diisopropylaniline is used to replace 2,6-dimethylaniline and 2-fluoro-2,6-dimethylbenzimine to react, Other operating conditions are the same. 5.31 g of 2-fluoro-2,6-dimethylbenzimine was reacted with 5.10 mL of 2,6-diisopropylaniline and 9.9 mL of n-BuLi (2.6M) to give pale yellow crystals (ligand L2) 3.99 g, 44.4% yield. Mass Spectrum EI-MS (m / z): 385.2[M] + . Elemental Analysis C 27 h 32 N 2 : Theoretical value: C, 84.26%; H, 8.46%; N, 7.28%. Found values: C, 84.21%; H, 8.48%; N, 7.06%.

[0026] Synthesis of compound 2:

[0027] According to the same synthetic method of compound 1 in Example 1, 1.21g ligand L2 and 1.7ml n-BuLi (2.6M) and 1.35g (DME) NiBr 2 After reaction, 1.51 g of dark green solid was obtained. Yield: 66.0%. Mass Spectrum EI-MS (m / z): 521, 522, 523, 524, 525, 526, (iso...

Embodiment 3

[0028] Embodiment 3: the synthesis of anilino imine nickel compound 3

[0029] Synthesis of Ligand L3:

[0030] 2-fluoro-2,6-diisopropylbenzimine (2-F-C 6 h 6 (CH=NC 6 h 3 i PR 2 -2,6)) Synthesis: 11.5g 2-fluorobenzaldehyde and 18.1g 2,6-diisopropylaniline were stirred in 40mL n-hexane for 2h, and the resulting bright yellow solution was frozen in a refrigerator at -10°C. 13.46 g of bright yellow crystals were obtained. After the filtrate was concentrated and cooled, another 4.3 g of crystals were obtained, and a total of 17.68 g of crystals was obtained. Yield 68%. Mass Spectrum EI-MS (m / z): 284.3 [M] + . Elemental Analysis C 19 h 22 NF: Theoretical: C, 80.53%; H, 7.83%; N, 8.94%. Found: C, 80.37%; H, 7.54%; N, 4.73%.

[0031] 14.8mL of n-BuLi hexane solution (2.6M) was slowly added dropwise into a 7.65mL 2,6-diisopropylaniline solution in tetrahydrofuran (40mL) at -78°C, stirred overnight and slowly rose to room temperature; then 10 g of 2-fluoro-2,6-diisopropy...

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Abstract

Production of random phenylethylene / norbornene polymer is carried out by taking catalyst consisting anilino-imino nickel compound and polyaluminum, polymerizing phenylethylene with norbornene and obtaining various polymer materials.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of random styrene / norbornene copolymer. Background technique [0002] Norbornene homopolymer has the advantages of high temperature resistance, chemical corrosion resistance, etc., but 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 The homopolymer has a certain degree of crystallinity, and the light transmission performance of the polymer is not good. Therefore, through the copolymerization of norbornene and α-olefin, the introduction of α-olefin between the norbornene chain segments can improve the performance of the polymer and obtain a cycloolefin copolymer (COC) with excellent performance. [0003] Cycloolefin copolymers not only have excellent heat resistance stability, light resistance, moisture resist...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F212/08C08F4/52C08F232/08
Inventor 高海洋伍青张玲祝方明林尚安
Owner CHINA PETROLEUM & CHEM CORP
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