Yasuo Moriya

New manufacturing processes for block and graft copolymers by radical reactions

Abstract New radical processes to obtain block and graft copolymers were developed by using special organic peroxides. Polymeric peroxides excelling in safety and solubility were newly prepared. PM 1 having OO bonds in its chain was prepared by polymerization of M 1 with polymeric peroxide, and M 2 was polymerized with PM 1 to provide PM 1 - b -PM 2 . A monomer having an OO bond was copolymerized with M 1 at a temperature below the decomposition temperature of the OO bond and PM 1 having pendant OO bonds was obtained. M 2 was addition-polymerized to pendant OO bonds to get PM 1 - g -PM 2 . Vinyl polymers having OO bonds were thermally mixed in an extruder with polyolefins and polyolefin- g -vinyl polymer was obtained by the reactive processing.

Synthesis and surfactant properties of novel fluoroalkylated allyl- and diallylammonium chloride oligomers

Abstract New fluoroalkylated allyl- and diallylammonium chloride oligomers with carbon—carbon bond formation have been prepared by the oligomerization of allylammonium chloride and the cyclo-oligomerization of diallylammonium chloride by the use of fluoroalkanoyl peroxides, respectively. These obtained fluoroalkylated cationic oligomers were able to reduce the surface tension of water to around 10 mN m−1, and are applicable to new cationic oligosurfactants containing fluoroalkyl groups.

Synthesis and surfactant properties of novel acrylic acid oligomers containing perfluoro-oxa-alkylene units: an approach to anti-human immunodeficiency virus type-1 agents

Abstract A new polymeric perfluoro-oxa-alkane diacyl peroxide has been prepared by the reaction of the corresponding perfluoro-oxa-alkane diacid fluoride and hydrogen peroxide under alkaline conditions. The decomposition behavior of this peroxide was quite similar to those of the fluoroalkanoyl peroxides [(RFCOO2)2; RF = perfiuoroalkyl and perfluoro-oxa-alkyl groups]. This peroxide decomposed homolytically with decarboxylation to afford the -RF- unit and, in addition, was useful for the introduction of the perfluoro-oxa-alkylene (-RF-) unit into acrylic acid homo- and co-oligomers via a radical process. These new acrylic acid oligomers containing the perfluoro-oxa-alkylene unit were shown to be soluble in water, methanol, ethanol, and tetrahydrofuran and were not only able to reduce the surface tension of water effectively but also to confer a good oil repellency. Furthermore, acrylic acid co-oligomers containing this perfluoro-oxa-alkylene unit were found to be potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) in vitro.

Synthesis and properties of fluoroalkylated vinyl alcohol oligomers

Abstract New fluoroalkylated vinyl alcohol oligomers were prepared by the alcoholysis of the corresponding fluoroalkylated vinyl acetate oligomers, which were obtained by the reactions of fluoroalkanoyl peroxides with vinyl acetate. These vinyl alcohol oligomers exhibited a quite different solubility from non-fluorinated poly(vinyl alcohol).

Synthesis and properties of novel fluoroalkylated allyl alcohol oligomers

Abstract Allyl alcohol and allyl alcohol containing the polyoxyethylene unit were found to react with fluoroalkanoyl peroxides to afford the corresponding fluoroalkylated allyl alcohol oligomers via a radical process under very mild conditions. In particular, fluoroalkylated allyl alcohol oligomers containing the polyoxyethylene unit were shown to be effective in reducing the surface tension of water, and to be applicable for new non-ionic fluorinated amphiphiles.

Synthesis of a novel polymeric perfluoro-oxa-alkane diacyl peroxide. A convenient tool for the introduction of the perfluoro-oxa-alkylene unit

A new polymeric perfluoro-oxa-alkane diacyl peroxide was prepared by the reaction of the corresponding perfluoro-oxa-alkane diacid fluoride and hydrogen peroxide, and this peroxide was shown to be useful for the introduction of the perfluoro-oxa-alkylene unit into acrylic acid oligomers.