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Ultra-high molecular weight poly(4-alkoxystyrene) and preparation method thereof

An alkoxystyrene, ultra-high molecular weight technology, used in chemical instruments and methods, platinum group organic compounds, organic chemistry, etc. Wide distribution and other problems, to achieve the effect of efficient and controllable polymerization reaction, excellent catalytic performance, and high polymerization activity

Active Publication Date: 2019-12-03
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

4-Alkoxystyrene is also prone to cationic polymerization, and its monomer conversion rate is relatively high. However, the reaction regulation of cationic polymerization is harsh, and various side reactions are very prone to occur, and it is difficult to obtain high molecular weight polymers (less than 100,000) , the molecular weight distribution of the polymer is relatively broad
However, due to the presence of polar methoxy groups and metal centers, the activity of these catalyst systems to catalyze the coordination polymerization of 4-alkoxystyrene is usually not high, and it is difficult to prepare narrow-distribution, ultra-high molecular weight poly(4-methyl oxystyrene), the molecular weight of the obtained polymers is all below 200,000

Method used

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  • Ultra-high molecular weight poly(4-alkoxystyrene) and preparation method thereof
  • Ultra-high molecular weight poly(4-alkoxystyrene) and preparation method thereof
  • Ultra-high molecular weight poly(4-alkoxystyrene) and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] This example provides a synthesis of α-diimine palladium complex 1. Its reaction scheme is as follows Figure 4 ,details as follows.

[0058] Synthesis of diketone: under nitrogen protection, anthracene (8.90 g, 50.0 mmol, 1 eq.) and vinylene carbonate (31.6 mL, 500.0 mmol, 10 eq.) were added to a 250 mL high-pressure reaction flask and heated to 180 ° C for reaction. After 8 hours, the heating was stopped, the reaction system was cooled to room temperature, and 150 mL of methanol was added. A large amount of solid was washed out from the reaction system, filtered, the solid was washed with methanol, and dried in vacuo to obtain a gray powder. Then this gray powder (5.60g, 21.0mmol, 1eq.) was dissolved in 50mL of absolute ethanol, potassium hydroxide (3.00g, 53.5mmol, 2.6eq.) was slowly added under stirring, and stirring was continued for 6 hours. The resulting mixed solution was filtered to remove suspended matter, and was slowly added dropwise to water, and a large...

Embodiment 2

[0062] This example provides a synthesis of α-diimine palladium complex 2. Its reaction scheme is as follows Figure 4 ,details as follows.

[0063] The synthesis of diketone is the same as in Example 1.

[0064] Synthesis of Ligand L2: Under a nitrogen atmosphere, diketone (2.34g, 10.0mmol, 1eq) and 2,6-dimethylaniline (2.7mL, 22.0mmol, 2.2eq) prepared in the above steps were dissolved in 100mL of toluene, Add p-toluenesulfonic acid, heat and reflux for 24 hours. The reacted mixture was rotary evaporated to remove the solvent, and the resulting solid was recrystallized from ethanol to obtain ligand L2 with a yield of 75%. 1 H NMR (CDCl 3 ,300MHz),δ(ppm):7.07-7.25(m,12H,Ar-H),4.91(s,2H,CH),2.53(m,4H,CH),1.23(s,18H,CH 3 ),1.15(m,12H,CH3),1.03(m,12H,CH 3 ). 13 C NMR (400MHz, CDCl 3 ), δ (ppm): 155.16, 143.22, 140.34, 136.77, 128.34, 126.65, 123.32, 122.31, 34.50, 31.36, 30.51, 28.94, 23.37.

[0065] Synthesis of α-diimine palladium complex 2: α-diimine methylpalladium c...

Embodiment 3

[0067] This example provides a synthesis of α-diimine palladium complex 3. Its reaction scheme is as follows Figure 4 ,details as follows.

[0068] The synthesis of diketone is the same as in Example 1.

[0069] Synthesis of Ligand L3: Under nitrogen atmosphere, diketone (2.34g, 10.0mmol, 1eq) and 2,6-diisopropylaniline (3.7mL, 22.0mmol, 2.2eq) prepared in the above steps were dissolved in 100mL of toluene , adding p-toluenesulfonic acid, heating to reflux for 24 hours. The reacted mixture was rotary evaporated to remove the solvent, and the resulting solid was recrystallized from ethanol to obtain ligand L3 with a yield of 82%. 1 H NMR (400MHz, CDCl 3 ),7.15-7.25(m,14H,Ar-H),4.97(d,2H,CH),2.51(m,4H,CH(CH 3 ) 2 ),1.16(d,12H,CH 3 ),1.03(d,12H,CH3 ). 13 C NMR (400MHz, CDCl 3 ), δ (ppm): 158.44, 145.59, 136.39, 127.30, 125.42, 124.15, 122.81, 51.15, 28.32, 23.29, 22.47.

[0070] Synthesis of α-diimine palladium complex 3: α-diimine methylpalladium chloride complex 3 is...

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Abstract

The invention relates to an ultra-high molecular weight poly(4-alkoxystyrene) and a preparation method thereof. The ultra-high molecular weight poly(4-alkoxystyrene) is of a structure as shown in a formula (I), wherein R is methyl or ethyl; and the weight-average molecular weight is not less than 1 million. The provided ultra-high molecular weight poly(4-alkoxystyrene) has the weight-average molecular weight of not less than 1 million, and better mechanical properties, thermal stability, and hydrophilic properties are realized comparing with commercial polystyrene .

Description

technical field [0001] The invention belongs to the technical field of olefin catalytic polymerization, and in particular relates to an ultrahigh molecular weight poly(4-alkoxystyrene) and a preparation method thereof. Background technique [0002] 4-Alkoxy styrene is a monomer with a polar alkoxy group, and functional polystyrene can be prepared by direct polymerization of this monomer. In addition to maintaining the excellent mechanical properties, dielectric properties, surface properties, barrier properties, solvent resistance and heat resistance of polystyrene, this kind of polymers also endows them with better hydrophilicity and adhesion. . In terms of polymerization mechanism, 4-alkoxystyrene can undergo free radical, cationic or coordination polymerization. Due to the electron-donating effect of the alkoxy group, the polymerization activity of the radical polymerization of 4-alkoxystyrene is relatively low, and the obtained poly(4-alkoxystyrene) molecular weight is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F112/14C08F4/26C07F15/00
CPCC07F15/006C08F112/14C08F2500/01C08F2500/03C08F4/26
Inventor 高海洋廖光福张智诚钟柳
Owner SUN YAT SEN UNIV
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