Poly(vinyl chloroformate) and its derivatives: 5. New poly(vinyl carbamates) and poly(vinyl thiocarbonates)

Kassir, Fathi; Boivin, Sylviane; Boileau, Sylvie; Cheradame, Hervé; Wooden, Gary P.; Olofson, R. A.

doi:10.1016/0032-3861(85)90209-5

Cited by 15 publications

(6 citation statements)

References 8 publications

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“…77 Boileau et al obtained high molecular weight poly(vinyl carbamates) in good yields by polymerization of a series of vinyl carbamates (25-28) using common thermal initiators like AIBN and DCPD. [33][34][35]78 Though vinyl carbonates gave low molecular weight polymers in poor yields when initiated with AIBN, polymerization of vinyl carbamates proceeded smoothly under the same conditions. From small sample data the authors concluded that the thermal stability of the polymers decreases in the following order: poly(O-vinyl carbamates) > poly(vinyl carbonates) > poly(O-vinyl thiocarbonates).…”

Section: Radical Polymerization With Thermal Initiatorsmentioning

confidence: 99%

“…28,29 Boileau's group then continued these studies over many years. 32,34,35,78,[86][87][88] For the polymerization they used more common thermal initiators like peroxydicarbonates, peroxides and AIBN. It was shown that high molecular weight poly(vinyl carbonates/carbamates) could be obtained by post-treatment of poly(VOC-Cl) with alcohols or amines with a degree of substitution close to 100%.…”

Section: Vinyl Chloroformate (Voc-cl)mentioning

confidence: 99%

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Vinyl carbonates, vinyl carbamates, and related monomers: synthesis, polymerization, and application

Husár

Liska

2012

Chem. Soc. Rev.

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Although acrylates and methacrylates are the state-of-the-art monomers for protective and decorative coatings, skin and inhalation irritancy and potential cytotoxicity of monomers present serious health hazards. Monomers like vinyl carbonates or vinyl carbamates can overcome these problems with their generally lower cytotoxicity and yet similar photoreactivity to (meth)acrylates. The reviewed classes of monomers have not attracted industry's attention until now due to expensive synthetic methods though recently developed affordable routes offer prospect for their increasing use (88 references).

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Section: Radical Polymerization With Thermal Initiatorsmentioning

confidence: 99%

Section: Vinyl Chloroformate (Voc-cl)mentioning

confidence: 99%

Vinyl carbonates, vinyl carbamates, and related monomers: synthesis, polymerization, and application

Husár

Liska

2012

Chem. Soc. Rev.

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“…Ceci nous a incites a examiner en dttail la polyrntrisation de ce monomere (6-8) et de quelques dtrivts (6,8,9) ainsi que la modification chirnique du polychloroforrniate de vinyle (6,(10)(11)(12). L'ernploi de peroxydicarbonates cornrne arnorceurs de la polyrntrisation radicalaire du chloroforrniate de vinyle, en rnasse et en solution, conduit a des polyrneres de masses rnolaires Clevtes (7,8).…”

Section: Introductionunclassified

Polymérisation du chloroformiate de vinyle et de ses dérivés

Boivin¹,

Hémery²,

Boileau³

1985

Can. J. Chem.

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Requ le 19 juin 1984Cet article esr rle'die' a la mkmoire de Monsieur Li Xiao-Bni SYLVIANE BOIVIN, PATRICK HEMERY et SYLVIE BOILEAU. Can. J . Chem. 63, 1337Chem. 63, (1985 La polymCrisation radicalaire du chloroformiate de vinyle a CtC Ctudiee dans le chlorure de mtthylkne a 35"C, avec le peroxydicarbonate de dicyclohexyle comme amorceur. Dcs mesures cinetiques ont Ct C effectuCes par dilatomktrie dans des appareils entikrement scellts sous vide pousse. L'ordre de la rkaction de polymCrisation par rapport B la concentration en monomkre est Cgal a I et celui relatif i la concentration en amorceur est Cgal B 0,5.Par ailleurs, des polymkres nouveaux ont CtC prCparCs soit par polymCrisation radicalaire de monomeres dCrivCs du chloroformiate de vinyle, soit par modification chimique du polychloroformiate de vinyle par des amines, des alcools, des thiols, des acides carboxyliques, KCN . . . , par catalyse par transfert de phase. La structure de ces polymkres ainsi que leur comportement thermique ont Ct C examinks. SYLVIANE BOIVIN, PATRICK HEMERY, and SYLVIE BOILEAU. Can. J . Chem. 63, 1337Chem. 63, (1985. The free-radical polymerization of vinyl chloroformate has been studied in methylene chloride at 3S°C using dicyclohexyl peroxydicarbonate as initiator. Kinetic measurements performed by dilatometry under high vacuum have shown that the reaction order in monomer is equal to one whereas that in catalyst is equal to 0.5.New polymers have been prepared either by free-radical polymerization of monomers derived from vinyl chloroformate or by chemical modification of poly(viny1 chloroformate) with amines, alcohols, thiols, carboxylic acids. KCN . . . using phase transfer catalysis. The structure of these polymers as well as their thermal behaviour have becn studied.

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“…Treatment of poly(vinyl chloroformate) with amines, alcohols, and phenols affords the corresponding poly(vinyl urethanes) and poly(vinyl carbonates). 16,18 Urethanes and carbonates of VOC-Cl also can be polymerized to similar materials with radical initiators. 16-19 These materials are hard (but not brittle) clear thermoplastics with high decomposition temperatures, excellent chemical resistance, and varying glass transition temperatures.…”

mentioning

confidence: 99%

“…16-19 These materials are hard (but not brittle) clear thermoplastics with high decomposition temperatures, excellent chemical resistance, and varying glass transition temperatures. 18 Some products have value as liquid crystals 20 and detergent builders. 21 The divinyl carbonate polymerizes an order of magnitude more easily than the diallyl carbonate to a product of similar properties.…”

mentioning

confidence: 99%