Extract obtained from the bark of Betula Pendula was treated with sodium hydroxide solution to obtain 4-(4-hydroxyphenyl) butan-2-one. New (meth)acrylates were synthesized on the basis of 4-(4-hydroxyphenyl)butan-2-one. Free radical polymerization of the new (meth)acrylates was compared with that of commercial monomers (e. g. phenyl(meth)acrylate, 2-phenoxyethyl methacrylate, and benzyl methacrylate) in solution resulting in soluble polymers as expected in all examples. In contrast to this, free radical polymerization of 4-(4-acryloylox-yphenyl)butan-2-one in bulk resulted in a crosslinked material although an extremely high molecular weight soluble polymer was received in case of bulk polymerization of 4-(4-methacryloyloxyphenyl)butan-2-one. The 3-oxobutyl substituent at the phenyl ring of these monomers may influence their radical polymerization. Furthermore, enzyme mediated radical polymerization and photoinitiated polymerization were applied for the polymer synthesis using 4-(4-methacryloyloxyphenyl)butan-2-one.

No abstract

Synthesis of statistical copolymers is described from bio‐based 4‐(4‐methacryloyloxyphenyl)butan‐2‐one (1) with an aliphatic methacrylate, such as n‐butyl methacrylate (2), N,N‐(dimethylamino)ethyl methacrylate (3), and lauryl methacrylate (4), using mostly dimethyl sulfoxide as solvent in the free radical polymerization. Though 4 is insoluble in dimethyl sulfoxide, diethyl carbonate is the preferred solvent for the copolymerization using this monomer although both yield and molecular weight are lower even for poly(4‐(4‐methacryloyloxyphenyl)butan‐2‐one) than using dimethyl sulfoxide as solvent. 1H NMR spectroscopic analysis gives information about the content on the monomer segments in all copolymers. Furthermore, elementary analysis additionally supports the results obtained for the copolymers made from 1 and 3. As shown by the copolymerization diagrams and the copolymerization parameters, the copolymerization of 1 with 2 is a nearly ideal copolymerization using short polymerization time (20 min). Extending the polymerization time results in slight deviation from an ideal copolymerization. Furthermore, the glass transition temperature of the copolymers determined by DSC and calculated using both the Fox equation and the Gibbs‐DiMarzio equation show the strong influence of the copolymer composition. As expected, the glass transition temperature increases with increasing content on aromatic segments in the copolymer that may be interesting for application in coatings and adhesives, respectively.

No abstract