Synthesis of cross-linked polymeric microparticles containing hexa-O-benzylsucrose

Figures & data

Table 1. Free radical copolymerization of sucrose monomers 2 and 3 with styrene.

Polymer	Monomers	^a	^b	Average length of linear polystyrene segments^b (number units)	Yield of solid polymer	Tg^c (°C)	Diameter of microparticles^d (nm)
4	2 + styrene	0.1	0.18	3	39%	85.7	380–750
5	3 + styrene	0.1	0.09	6	37%	75.4	600–800

^a Initial (feed) mol ratio of the monomers.

^b Mole ratio of the comonomers in the copolymer, determined indirectly by ¹H-NMR of the soluble fraction.

^c Determined by DSC.

^d Determined by AFM.

Figure 1. AFM images of polymeric particles 4 and 5.

Scheme 1. Synthesis of sucrose-containing monomers from 1′,2,3,3′,4,4′-hexa-O-benzylsucrose 1. (i) (CH₂=C(CH₃)CO)₂O, CH₂Cl₂, Et₃N, DMAP, 35 ºC, 300 W, 10 min, 65% or rt, 4 h, 69%. (ii) CH₂=CH–CH₂–Br, NaH, DMF, 145 °C, 300 W, 10 min, 74% or rt, 3 h, 79%.

Scheme 2. Synthesis of the cross-linked polymer 4.

Scheme 3. Synthesis of the cross-linked polymer 5.