Stereospecific radical polymerization of fluoroalkyl acrylates

Liu, Weihong

doi:10.1002/(sici)1099-0518(20000315)38:6<1024::aid-pola12>3.0.co;2-d

Cited by 16 publications

(6 citation statements)

References 12 publications

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“…By optimization of the conditions, the racemo contents reached r ) 81% for the polymerization of 1,1,1,3,3,3-hexafluoro-2-propyl acrylate (BM-62). 285 2,2,2-Trifluoroethyl methacrylate (BM-64) gave syndiotactic-rich polymer but almost the same tacticity as that for the corresponding nonfluoro methacrylate (rr ) 56% at 60°C). 286 …”

Section: Polymerization Of Bulky Monomersmentioning

confidence: 99%

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

2009

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Section: Polymerization Of Bulky Monomersmentioning

confidence: 99%

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

2009

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“…cently, we found that the stereochemistry of radical polymerization of triphenylmethyl methacrylate was remarkably dependent on monomer concentration.2 A clear concentration effect was also found in the radical polymerization of l,l,l,3,3,3-hexafluoro-2-propyl acrylate at low temperature. 4 In the present work, monomer concentration effect on the stereochemistry in the polymerization of DMAA in toluene and (CF 3 ) 3 COH was investigated. As shown in Table I ( [M] 0 = 1.0 M and 9.8 M) and Table II, in both solvents, a higher m specificity was observed at a lower monomer concentration.…”

Section: Dmaa Monomer Concentration Effectmentioning

confidence: 99%

“…This result is similar to those in the polymerization of l,l,1,3,3,3-hexafluoro-2-propyl acrylate in THF. 4 Polym. J .• Vol.…”

Section: Dmaa Monomer Concentration Effectmentioning

confidence: 99%

“…Control of the stereochemistry (tacticity) in free-radical polymerization is especially intriguing since there are only limited successful examples in spite of the convenience and industrial importance of radical polymerization. 1 Several methods have been devised to control the stereochemistry of radical polymerization of methacrylates, i -3 acrylates, 4 acrylamides, 5 • 6 and vinyl esters. 7 It has been recognized that stereocontrol of acrylic monomers, in contrast to that of methacrylic counterparts, is generally difficult due to the lack of a-CH 3 group: for example, methyl acrylate (MA) gives an atactic polymer regardless of reaction conditions of radical polymerization 8 while methyl methacrylate (MMA) affords a highly syndiotactic polymer by radical mechanism under selected conditions.…”

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confidence: 99%

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Stereocontrol in Radical Polymerization of N,N-Dimethylacrylamide and N,N-Diphenylacrylamide and Thermal Properties of Syndiotactic Poly(methyl acrylate)s Derived from the Obtained Polymers

Liu

2000

Polym J

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Free-radical polymerizations of N,N-dimethylacrylamide (DMAA) and N,N-diphenylacrylamide (DPAA) were carried out under various conditions. DMAA gave an isotactic-rich polymer in most cases, whereas DPAA gave a syndiotactic polymer. The polymerization stereochemistry was also affected by reaction solvents including toluene, tetrahydrofuran, and fluoroalcohols. It is notable that the stereochemistry of the polymerization depended on monomer concentration: a lower monomer concentration led to a higher isotacticity for DMAA polymerization and a higher syndiotacticity for DPAA polymerization. This effect was explained by assuming that there exist two types of growing radicals having different stereoselectivities. By optimizing the aforementioned reaction conditions, poly(DMAA) with diad isotacticity (m) of 77% (polymerization in toluene at-78°C at [M] 0 =0.1 M) and poly(DPAA) with diad syndiotacticity (r) of93% (polymerization in THF at-98°C at [Mlo=0.22M) were obtained. Stereoregular poly(methyl acrylate)s were derived from the poly(DPAA)s. Thermal property of the poly(methyl acrylate)s with different tacticities was studied by DSC.

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“…In addition, adequate design of monomers led to effective stereoregulation. [4][5][6][7][8] In this work, the stereochemistry of radical polymerization of N-methyl methacrylamide (N-MMAm) was studied. This type of monomer is often used to prepare water-soluble polymers for biomedical purposes; however, the examples of stereochemical study on the polymerization of methacrylamide and its derivatives are limited and only moderate tacticity (syndiotactic triad (rr) of 65-68%) has been achieved.…”

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Stereospecific Radical Polymerization of N-Methyl Methacrylamide

Zhang

Liu

Nakano

et al. 2000

Polym J

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N-Methyl methacrylamide (N-MMAm) was polymerized using radical initiators under various conditions. The triad tacticity of the obtained polymers was determined by 100 MHz 13 C NMR. The polymers were rich in syndiotactic configuration. At a given temperature, the syndiotacticity increased with an increase in solvent polarity. This solvent effect may have connection with the hydrogen bonding interaction among solvent, monomer, and growing species. The fraction of rr triad increased with decreasing polymerization temperature in all solvents. Monomer concentration also affected the stereochemistry of the polymerization. By optimizing conditions, a high rr specificity (rr =95%) was achieved. Thermal property of the poly(N-MMAm)s with different tacticities was studied by DSC.KEY WORDS Radical Polymerization/ Tacticity / Stereochemistry / Solvent Effect/ Syndiotacticity / Methacrylamides /

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Stereospecific radical polymerization of fluoroalkyl acrylates

Cited by 16 publications

References 12 publications

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

Stereospecific Living Radical Polymerization: Dual Control of Chain Length and Tacticity for Precision Polymer Synthesis

Stereocontrol in Radical Polymerization of N,N-Dimethylacrylamide and N,N-Diphenylacrylamide and Thermal Properties of Syndiotactic Poly(methyl acrylate)s Derived from the Obtained Polymers

Stereospecific Radical Polymerization of N-Methyl Methacrylamide

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