The reactivity of vinylaryl ethers during copolymerization with vinylchloride and vinylidenechloride

Deryabina, G. I.; Frolov, Yu. L.; Kalabina, A. V.

doi:10.1016/0032-3950(71)90340-6

Polymer Science U.S.S.R.

1971

DOI: 10.1016/0032-3950(71)90340-6

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The reactivity of vinylaryl ethers during copolymerization with vinylchloride and vinylidenechloride

G. I. Deryabina

Yu. L. Frolov

A. V. Kalabina

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Cited by 2 publications

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“…[8][9][10][11]. The significant acetylene consumption and the formation of tars in these syntheses (growing with the increasing concentration of water in the system) is apparently due to the phenolate condensation with acetaldehyde arising through acetylene hydration.…”

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confidence: 99%

“…The pioneering research in this field was carried out by the scientific school of A.V. Kalabina [2-4] who widely used aryl vinyl ethers for the preparation of polymer materials [5][6][7][8][9][10][11][12], in the diene synthesis [13][14][15][16], and also in the design of biologically active compounds, in particular, of insecticides and herbicides [17]. The chemistry of aryl vinyl ethers has been actively developed in the recent decades [18][19][20][21].…”

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Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene

et al. 2015

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Phenols and naphthols react with acetylene in a superbasic system KOH-DMSO forming the corresponding aryl vinyl ethers in up to 80% yields. * For communication XVII, see [1].Aryl vinyl ethers compared with aliphatic analogs are more stable against hydrolysis and are more reactive in the radical polymerization. They are highly reactive building blocks for organic synthesis. The pioneering research in this field was carried out by the scientific school of A.V. Kalabina [2-4] who widely used aryl vinyl ethers for the preparation of polymer materials [5][6][7][8][9][10][11][12], in the diene synthesis [13][14][15][16], and also in the design of biologically active compounds, in particular, of insecticides and herbicides [17]. The chemistry of aryl vinyl ethers has been actively developed in the recent decades [18][19][20][21]. They were utilized for designing new polymer compositions [20,21], reagents for the chemical plant protection [22]. A high selectivity of aryl vinyl ethers was found at the ammetric titration of metal ions, in particular, of Ag(I) [23]. Vinyl ether of fluorescein was recommended as a highly sensitive fluorescent probe for organomercury compounds in cells and living bodies [24]. New methods of aryl vinyl ethers production are under development, among which the following are worth considering: catalytic reaction of phenols with various vinyl equivalents, e.g., vinyl halides [25, 26], vinylboronic acids [27, 28], tetravinyl-and tributyl-(vinyl)tin [29], vinyl esters of carboxylic acids [21, 30], and also the synthesis of aryl vinyl ethers from 2-phenylselenyl-ethanol [31-33] or 2-phenylsulfonylethanol [34] and phenols at treating with Mitsunobu reagent (diethyl ether of azodicarboxylic acidtriphenylphosphine). Recently a new two-stage method was patented of the production of aromatic vinyl ethers in a low yield (10-38%) involving vinylation of 2-aryloxyethanols (100 о С, 3-6 h, acetylene pressure 1.4 at, KОН-DMSO) with the formation of the corresponding 2-aryloxyethyl vinyl ethers followed by heating of the latter (130-140 о С, 6-10 h, DMSO) in the presence of double molar excess of KОН [35].The classic synthesis method of aryl vinyl ether through direct phenol vinylation with acetylene under the basic catalysis conditions not only conserves its importance but possesses obvious advantages before the mentioned procedures [21,[25][26][27][28][29][30][31][32][33][34][35] since it is atomeconomical, one-stage, and is based on a raw material of a large-scale production. Phenols add to acetylene in the presence of KОН at a high pressure (30-50 at) and a high temperature (180-200 о С) [2,[36][37][38][39][40].The aim of this study is the development of a technologically more convenient procedure of the synthesis of aryl vinyl ethers by vinylation of phenols and naphthols with acetylene in superbasic catalytic environment (alkali metal hydroxide-polar hydroxylfree solvent). The application of superbasic media in the acetylene chemistry made it possible to improve the most important reactions of nucleophili...

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Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene

et al. 2015

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Relative reactivities and graft distributions of polystyrene Macromers® in vinyl chloride copolymerization

Schulz¹,

Milkovich²

1994

Polymer International

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Polystyrene macromonomers terminated with methacrylate, vinyl ether, or maleic half ester functionalities were evaluated in free radical initiated copolymerizations with vinyl chloride in aqueous suspension polymerization. Macromers® (M1) terminated with methacrylate disappeared very rapidly in copolymerization with vinyl chloride (M2). The relative reactivity ratio, r2, was determined to be 0.05 in good agreement with literature values of about 0.04. Vinyl ether‐terminated Macromers® had unexpectedly uniform reactivity with vinyl chloride in early conversion samples, but macromonomer conversion was incomplete. Macromers® having maleic half ester functionality were incorporated rapidly in vinyl chloride copolymerization at pH 2.5 (r2 = 0.13). However, at pH 10 these Macromers® had reduced reactivity (r2 = 0.34), which improved graft polymer uniformity. These Macromer® copolymerization relative reactivities are shown to be useful in predicting and controlling graft densities and graft polymer heterogeneity which influence morphology, processing, and mechanical properties.

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The reactivity of vinylaryl ethers during copolymerization with vinylchloride and vinylidenechloride

Cited by 2 publications

References 6 publications

Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene

Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene

Relative reactivities and graft distributions of polystyrene Macromers® in vinyl chloride copolymerization

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