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Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating.

ABSTRACT: A new structural fluorine-containing methacrylate monomer CH?=C(CH?)COOC?(CF?)?CF?CF?CF? (5) was synthesized derived from perfluoro-2-methyl-2-pentene (D?). A homopolymer of 5 and copolymers of 5 and methacrylate with different alkyl chain length (chain length n = 1, 2, 4, 6, 8, 12, 18) were obtained. These new fluorinated acrylate polymers showed excellent water and oil repellency. The contact angle of the films of the homopolymer and part of the copolymers were similar with the corresponding polymers prepared from CH?=CHC(O)OCH(C?F?)(CF(CF?)?), but greater than that of the C?F₁₃(CF?)CHOC(O)CH=CH? homopolymer. The structure-property relationship research indicated that the copolymers' hydrophobicity decreased first and then increased with the increase of alkyl chain length. T_d of all the polymers were greater than 220 °C and T_g fluctuated within the range of -51~103.8 °C. Contact angle and T_g could be adjusted by controlling the feed ratio of monomer to meet the requirements of technical indicators in the practical applications. The outstanding liquid repellency and thermal stability make monomer 5 a promising alternative to perfluorinated long-chain fluorosurfactants.

SUBMITTER: Zhang D

PROVIDER: S-EPMC6266613 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating.

Zhang Ding D Xing Ping P Pan Renming R Lin Xiangyang X Sha Min M Jiang Biao B

Materials (Basel, Switzerland) 20181113 11

A new structural fluorine-containing methacrylate monomer CH₂=C(CH₃)COOC⁻(CF₃)₂CF₂CF₂CF₃ (5) was synthesized derived from perfluoro-2-methyl-2-pentene (D₂). A homopolymer of 5 and copolymers of 5 and methacrylate with different alkyl chain length (chain length n = 1, 2, 4, 6, 8, 12, 18) were obtained. These new fluorinated acrylate polymers showed excellent water and oil repellency. The contact angle of the films of the homopolymer and part of the copolymers were simi ...[more]

PMID: 30428523

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Project description:Aminomethylation reactions between chiral amino compounds (S)-(-)-1-phenylethylamine and l-proline with tetranonylresorcinarene and tetra-(4-hydroxyphenyl)resorcinarene in presence of formaldehyde were studied. The reaction between l-proline and resorcinarenes generated regioselectively chiral tetra-Mannich bases, due to the molecular incorporation of the fragment of the chiral amino acid. On the other hand, tetranonylresorcinarene and (S)-(-)-1-phenylethylamine formed regio- and diasteroselectively chiral tetrabenzoxazines, both by chiral auxiliary functionalization and by the transformation of the molecular structure that confers inherent chirality. The products obtained were characterized using IR, 1H-NMR, 13C-NMR, COSY, HMQC, and HMBC techniques. The reaction of (S)-(-)-1-phenylethylamine with tetra-(4-hydroxyphenyl)resorcinarene did not proceed under the experimental conditions. Once the chiral aminomethylated tetra-(4-hydroxyphenyl)resorcinarene was obtained, the chemical modification of poly(GMA-co-EDMA) was studied, and the results showed an efficient incorporation of the aminomethylated compound. For the physical modification, chiral aminomethylated tetranonylresorcinarenes were employed, finding that the incorporation of modified resorcinarenes occurs, but with less efficiency than that observed using chemical modification. The modified polymers were characterized via FT-IR, scanning electron microscopy imaging, and elemental analysis. Finally, polymers modified with chiral resorcinarenes were used as sorbents in norepinephrine microextraction; for practical purposes, artificial urine was prepared and used. To perform the microextraction, the decision was made to use the modern rotating-disk sorptive extraction technique (RDSE), because of its analytical attributes as a green, or eco-friendly, technique. According to the results, the method preliminarily validated for the determination of norepinephrine in artificial urine shows that the modified polymer with chiral derivative of tetra-(4-hydroxyphenyl)resorcinarene worked effectively as a new sorbent phase for the quantitative microextraction of norepinephrine, exhibiting high stability and homogeneity of composition and structure within the working range.

Dataset Information

Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating.

Publications

Preparation and Surface Properties Study of Novel Fluorine-Containing Methacrylate Polymers for Coating.

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