Polymeric Linoleic Acid–Polyolefin Conjugates: Cell Adhesion and Biocompatibility

Abstract

To diversify edible-oil polymer composite, polymeric linoleic acid (PLina) peroxide was obtained by the auto-oxidation of linoleic acid in a simple way for use as a macroinitiator in free radical polymerization of vinyl monomers. Peroxidation, epoxidation, and/or perepoxidation reactions of linoleic acid under air at room temperature resulted in PLina, having soluble fraction more than 91 weight percent (wt%), with molecular weight ranging from 1,644 to 2,763 Da, and containing up to 1.0 wt% of peroxide. PLina initiated the free radical polymerization of ether styrene (S), methyl methacrylate (MMA), or n-butyl methacrylate (nBMA) to give PLina-g-polystyrene (PS), PLina-g-poly-MMA (PMMA), and PLina-g-polynBMA (PnBMA) graft copolymers. The polymers obtained were characterized by proton nuclear magnetic resonance ( 1 H NMR), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), and gel permeation chromatography (GPC) techniques. Microstructure of the graft copolymers was observed by using scanning electron microscope (SEM). Graft copolymers obtained contained polymeric linoleic acid in a range between 8.5 and 19.3 mol percent (mol%). PLina-g-PS, PLina-g-PMMA andPLina-g-PnBMA graft copolymer samples were also used in cell culture studies. Fibroblast and macrophage cells were strongly adhered and spread on the copolymer film surfaces. These newly synthesized copolymers were tested for their effects on human blood protein adsorption compared with PMMA graft copolymers containing polymeric soybean oil and polymeric linseed oil; interestingly we observed a dramatic decrease in the protein adsorption on the linoleic acid graft copolymer, which is important in tissue engineering.

In Vitro characterization of low modulus linoleic acid coated strontium‐substituted hydroxyapatite containing PMMA bone cement

“…16 On this basis, our group developed linoleic acid-functionalized strontium substituted hydroxyapatite particles (Sr5-HA) by using the liquid-solid solution method. 17 We hypothesize that the addition of Sr5-HA and linoleic acid in the liquid phase could reduce the modulus of the bone cement.…”

Effects of different epoxidation methods of soybean oil on the characteristics of acrylated epoxidized soybean oil-co-poly(methyl methacrylate) copolymer

“…According to Hazer and coworkers [26][27][28][29][30][31][32][33], vegetable oils were autooxidized by exposure to sunlight or daylight in air for a given time to produce epoxides, peroxides, peroxides, and hydroperoxides in the molecular chains and were also graft copolymerized by free radical polymerization with other materials such as methyl methacrylate and styrene. Recently, the vegetable oil-based polymers have been prepared by cationic, olefin metathesis and condensation polymerization reactions, including the use of 'click' chemistry and carbon dioxide [5,[34][35][36][37].…”

Synthesis and Characterization of Poly(N‐Isopropyl Acryl Amide)‐g‐Poly(Linoleic Acid)/Poly(Linolenic Acid) Graft Copolymers

“…For the autoxidation of linoleic acid and linolenic acid, the same procedure reported in the literature [18] was used. Briefly, 5.0 g of linoleic acid (or linolenic acid) spread out in a Petri dish ([ = 5 cm) was exposed to sunlight in the air at room temperature.…”

“…Oxidation is initiated by abstraction of the bis-allylic hydrogen atom generating a radical, which can undergo trapping at either terminus or at the central (bis-allylic) position. These oil/ oily acid macroperoxides can initiate the free radical polymerization of vinyl monomers, leading to graft copolymers [17][18][19]. To the best of our knowledge, there are no papers describing PNIPAM copolymers containing polyunsaturated fatty acids.…”