Abstract
A novel initiator, bromoester modified 4-n-butylresorcinol (4nBREBr2), was prepared and utilized in controlled atom transfer radical polymerization (ATRP) to obtain three series of amphiphilic copolymers. The V-shaped copolymers of methyl methacrylate (MMA), 2-hydroxyethyl methacrylate (HEMA), and poly(ethylene glycol) methyl ether methacrylate (MPEGMA), abbreviated to P(HEMA–co–MMA), P(HEMA–co–MPEGMA), and P(MMA–co–MPEGMA), were synthesized. Moreover, P((HEMA–graft–PEG)–co–MMA) graft copolymers were prepared by combining the pre-polymerization modification of HEMA and a “click” reaction using a “grafting onto” approach. All copolymers could form micelles with encapsulated active substances (vitamin C (VitC), vitamin E (VitE), arbutin (ARB)), which are used in cosmetology. In vitro studies carried out in a PBS solution (pH 7.4) demonstrates that in most cases the maximum release of active substance was after 1 h. The polymeric systems presenting satisfactory encapsulation characteristics and release profiles are attractive micellar carriers of cosmetic substances, which show a positive effect on the skin condition.
Highlights
A novel initiator, bromoester modified 4-n-butylresorcinol (4nBREBr2 ), was prepared and utilized in controlled atom transfer radical polymerization (ATRP) to obtain three series of amphiphilic copolymers
Four series of copolymers were synthesized by pseudo-living ATRP, which was initiated by
Four series of copolymers were synthesized by pseudo-living ATRP, which was initiated by bromoester-functionalized 4-n-buthylresorcinol (4nBREBr2) and catalyzed with CuBr/dNbpy in bromoester-functionalized 4-n-buthylresorcinol (4nBREBr2 ) and catalyzed with CuBr/dNbpy in anisole anisole or anisole/methanol at 60 °C
Summary
A novel initiator, bromoester modified 4-n-butylresorcinol (4nBREBr2 ), was prepared and utilized in controlled atom transfer radical polymerization (ATRP) to obtain three series of amphiphilic copolymers. P((HEMA–graft–PEG)–co–MMA) graft copolymers were prepared by combining the pre-polymerization modification of HEMA and a “click” reaction using a “grafting onto” approach. All copolymers could form micelles with encapsulated active substances (vitamin C (VitC), vitamin E (VitE), arbutin (ARB)), which are used in cosmetology. In vitro studies carried out in a PBS solution (pH 7.4) demonstrates that in most cases the maximum release of active substance was after 1 h. The polymeric systems presenting satisfactory encapsulation characteristics and release profiles are attractive micellar carriers of cosmetic substances, which show a positive effect on the skin condition. 4-n-Butylresorcinol (4nBRE) is a derivative of retinol (RET, commonly known as vitamin A), which is widely used in cosmetic products such as anti-wrinkle creams and used to reduce discoloration
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