Synthesis, UV-curing Behavior and Surface Properties of New Fluorine-containing Aromatic Oxetane Monomers

Shu-Qing Fang; Yu-Lian Pang; Ying-Quan Zou

doi:10.1007/s10118-018-2048-4

Your Location：

Home >

Browse articles >

Synthesis, UV-curing Behavior and Surface Properties of New Fluorine-containing Aromatic Oxetane Monomers

Articles | Updated：2021-02-18

- Synthesis, UV-curing Behavior and Surface Properties of New Fluorine-containing Aromatic Oxetane Monomers
- Chinese Journal of Polymer Science Vol. 36, Issue 4, Pages: 521-527(2018)
- Affiliations：
  
  College of Chemistry, Beijing Normal University, Beijing 100875, China
- Author bio：
  
  E-mail zouyq@263.net
- Funds：
- DOI：10.1007/s10118-018-2048-4
  CLC：
- Received：24 May 2017，
  
  Accepted：22 September 2017，
  
  Online First：20 December 2017，
  
  Published：05 April 2018
- Accepted：
Scan QR Code
Shu-Qing Fang, Yu-Lian Pang, Ying-Quan Zou. Synthesis, UV-curing Behavior and Surface Properties of New Fluorine-containing Aromatic Oxetane Monomers[J]. Chinese Journal of Polymer Science, 2018, 36(4): 521-527.
DOI：

Shu-Qing Fang, Yu-Lian Pang, Ying-Quan Zou. Synthesis, UV-curing Behavior and Surface Properties of New Fluorine-containing Aromatic Oxetane Monomers[J]. Chinese Journal of Polymer Science, 2018, 36(4): 521-527. DOI： 10.1007/s10118-018-2048-4.

摘要

Abstract

In this paper

we combined high-end cationic UV-curable material with fluorinated chain obtaining a series of new fluorine-containing aromatic oxetane monomers

via

a mild nucleophilic substitution reaction. The structures and properties of monomers were characterized using

H-NMR

F-NMR

dynamic viscosity tests and differential scanning calorimetry (DSC). It was determined that all of the fluorinated monomers obtained had much lower viscosity and higher thermostability after the introduction of hexafluorobenzene. Then

UV-curable coatings were prepared using four fluorine-containing aromatic oxetane monomers (FOX1-4); the UV-curing kinetics

with three kinds of initiators

and properties of the cured films were evaluated using real-time Fourier transform infrared (FTIR) spectroscopy

water and diiodomethane contact angle tests

surface energy calculations and scanning electron microscopy (SEM). The FTIR spectroscopy results showed that the coatings possessed excellent conversion rate (

99% with liquid initiator PAG-201 in 150 s)

and as the fluorine content increased

the monomers exhibited decreased mobility with the increasing viscosity and worse solubility with fluorinated monomers

resulting in a lower conversion rate. Moreover

the coatings possessed favorable hydrophobic and oleophobic properties and low surface energies owing to the fluoride chains floating to the membrane-air interface

which was also confirmed by discrete concave structures in SEM images. These new kinds of monomers can replace traditional fluorinated cationic monomers applied to the fingerprint resistant

fouling resistant

scratch resistant and anti-aging coatings

adhesives or printing ink materials.

关键词

Keywords

references

M. Sangermano , R. Bongiovanni , G. Malucelli , A. Priola , R. R. Thomas , R. E. Medsker , Y. Kim , C. M. Kausch . Synthesis and cationic photopolymerization of a new fluorinated oxetane monomer . Polymer , 2004 . 45 ( 7 ): 2133 - 2139 . DOI: 10.1016/j.polymer.2004.01.046 http://doi.org/10.1016/j.polymer.2004.01.046 .

J. Yang , W. Y. Huang . Synthesis and characterization of a novel fluorine-containing hydrophobically associating polymer . Chinese J. Polym. Sci. , 1999 . 17 ( 3 ): 281 - 288 . http://en.cnki.com.cn/Article_en/CJFDTOTAL-GFZK199903010.htm http://en.cnki.com.cn/Article_en/CJFDTOTAL-GFZK199903010.htm , .

S. C. Wan , B. W. Huang , Z. P. Du . Study on the synthesis of 3, 3'-[1, 4-butanediylbis(oxymethylene)]bis[(3-ethyl)oxetane] for the novel cationic curing monomer . Imag. Sci. Photochem. , 2016 . 181 - 189 . https://link.springer.com/article/10.1007/s10118-018-2048-4 https://link.springer.com/article/10.1007/s10118-018-2048-4 , .

P. Kurt , K. J. Wynne . Co-polyoxetanes with alkylammonium and fluorous or PEG-like side chains:soft blocks for surface modifying polyurethanes . Macromolecules , 2007 . 40 ( 26 ): 9537 - 9543 . DOI: 10.1021/ma071763a http://doi.org/10.1021/ma071763a .

O. Škola , B. Jašúrek , D. Veselý , P. Němec . Mechanical properties of polymer layers fabricated via hybrid free radical-cationic polymerization of acrylate, epoxide, and oxetane binders . Prog. Org. Coat. , 2016 . 101 279 - 287 . DOI: 10.1016/j.porgcoat.2016.08.020 http://doi.org/10.1016/j.porgcoat.2016.08.020 .

Y. Nakano , H. Tsutsumi . Ion conduction and electrochemical performance of poly(oxetane)-based electrolytes with tri(cyanoethoxymethyl) moiety as a side chain . ECS Transactions , 2014 . 62 ( 1 ): 255 - 263 . DOI: 10.1149/06201.0255ecst http://doi.org/10.1149/06201.0255ecst .

F. Zhan , X. Cheng , W. F. Shi . Synthesis and properties of oxetane-based polysiloxanes used for cationic UV curing coatings . Polym. Adv. Technol. , 2012 . 23 ( 3 ): 645 - 651 . DOI: 10.1002/pat.v23.3 http://doi.org/10.1002/pat.v23.3 .

R. Bongiovanni , G. Malucelli , M. Sangermano , A. Priola . Fluorinated networks through photopolymerisation processes:synthesis, characterisation and properties . J. Fluorine Chem. , 2004 . 125 ( 2 ): 345 - 351 . DOI: 10.1016/j.jfluchem.2003.07.017 http://doi.org/10.1016/j.jfluchem.2003.07.017 .

H. Mou , L. Chen , C. Wang , Y. L. Wang , X. L. Wang . Paint Coat . Ind. , 2015 . 2 1 - 6 . http://www.astm.org/Standards/paint-and-related-coating-standards.html http://www.astm.org/Standards/paint-and-related-coating-standards.html , .

J. Q. Tan , W. Q. Liu , Z. F. Wang . Preparation and performance of waterborne UV-curable polyurethane containing long fluorinated side chains . J. Appl. Polym. Sci. , 2017 . DOI: 10.1002/app.44506 http://doi.org/10.1002/app.44506 .

B. Liu , Y. Bao , H. F. Ling , W. S. Zhu , R. J. Gong , J. Y. Lin , L. H. Xie , M. D. Yi , W. Huang . Fluorinated p-n type copolyfluorene as polymer electret for stable nonvolatile organic transistor memory device . Chinese J. Polym. Sci. , 2016 . 34 ( 10 ): 1183 - 1195 . DOI: 10.1007/s10118-016-1826-0 http://doi.org/10.1007/s10118-016-1826-0 .

W. Li , P. Feng , Y. Q. Zou , B. Hai . Synthesis and cationic photopolymerization of fluorine-containing vinyl ether monomers for the hydrophobic films . J. Appl. Polym. Sci. , 2014 . 131 ( 21 ): 41019 http://onlinelibrary.wiley.com/resolve/doi?DOI=10.1002%2Fapp.38943 http://onlinelibrary.wiley.com/resolve/doi?DOI=10.1002%2Fapp.38943 , .

W. Li , ou Z , Q. Synthesis Y. . UV-curing behavior and surface properties of fluorine-containing vinyl ether polymers . Chinese J. Polym. Sci. , 2014 . 32 ( 8 ): 1032 - 1039 . DOI: 10.1007/s10118-014-1485-y http://doi.org/10.1007/s10118-014-1485-y .

T. C. Canak , E. Hamuryudan , I. E. Serhatli . Synthesis and characterization of perfluorinatedacrylatemethyl methacrylate copolymers . J. Appl. Polym. Sci. , 2013 . 128 ( 3 ): 1450 - 1461 . http://onlinelibrary.wiley.com/doi/10.1002/app.38128/epdf http://onlinelibrary.wiley.com/doi/10.1002/app.38128/epdf , .

Y. Lin , K. Liao , C. Huang , N. Chou , S. Wang , S. Chu , K. Hsieh . Superhydrophobic films of UV-curable fluorinated epoxy acrylate resins . Polym. Int. , 2010 . 59 ( 9 ): 1205 - 1211 . DOI: 10.1002/pi.2848 http://doi.org/10.1002/pi.2848 .

J. Wang , J. Q. Huang , Y. G.; Qing F. L. Huang . Synthesis and characterization of novel oxetane monomers containing short perfluorocarbon side chains . Chinese J. Org. Chem. , 2009 . 1969 - 1974 . https://www.sciencedirect.com/science/article/pii/S016943320600612X https://www.sciencedirect.com/science/article/pii/S016943320600612X , .

K. Xie , A. Hou , Y. Shi . Synthesis of fluorine-containing acrylate copolymer and application as resinson dyed polyester microfiber fabric . J. Appl. Polym. Sci. , 2008 . 108 ( 3 ): 1778 - 1782 . DOI: 10.1002/(ISSN)1097-4628 http://doi.org/10.1002/(ISSN)1097-4628 .

P. Kurt , A. Chakravorty , X. M. Zeng , K. J. Wynne . Strongly amphiphilic wetting behavior for polyurethanes with polyoxetane soft blocks having-CF 2 H terminated side chains . Polymer , 2014 . 55 ( 9 ): 2170 - 2178 . DOI: 10.1016/j.polymer.2014.03.011 http://doi.org/10.1016/j.polymer.2014.03.011 .

C. Deng , W. F. Xie , B. W. Huang . Study on the properties of oxetane/acrylate UV-cured hybrid system . Imag. Sci. Photochem. , 2014 . 289 - 299 . https://www.researchgate.net/publication/288540363_Study_on_the... https://www.researchgate.net/publication/288540363_Study_on_the... , .

S. Yang , J. Jin , S. Kwak , B. Bae . Photocurable transparent cycloaliphatic epoxy hybrid materials crosslinked by oxetane . J. Appl. Polym. Sci. , 2012 . 126 ( S2 ): E380 - E386 . DOI: 10.1002/app.36654 http://doi.org/10.1002/app.36654 .

F. Zhan , Y. Zhang , W. F. Shi . Synthesis of perfluorinated oxetane and surface properties of its cationic UV cured coating as a reactive additive . Chem. Res. Chinese U. , 2012 . 28 ( 3 ): 550 - 558 . https://www.researchgate.net/publication/267940436_Synthesis_of... https://www.researchgate.net/publication/267940436_Synthesis_of... , .

A. Ertekin , Y. Kim , C. M. Kausch , R. R. Thomas . Adsorption properties of oligo(fluorooxetane)-b-poly(ethylene oxide)-b-oligo(fluorooxetane) triblock copolymers at the air-water interface:comparison of hydroxyl and acetate end groups . J. Colloid Interf. Sci. , 2009 . 336 ( 1 ): 40 - 45 . DOI: 10.1016/j.jcis.2009.03.043 http://doi.org/10.1016/j.jcis.2009.03.043 .

B. J. Song , J. K. Park , H. K. Kim . Novel photocurable multifunctional acrylate monomers containing perfluorinated aromatic units and their copolymers for photonic applications . J. Polym. Sci., Part A:Polym. Chem. , 2004 . 42 ( 24 ): 6375 - 6383 . DOI: 10.1002/(ISSN)1099-0518 http://doi.org/10.1002/(ISSN)1099-0518 .

H. T. Liu , J. H. Mo , H. C. Liu . HuaZhong U.Sci. Technol. . Nat. Sci. Ed. , 2008 . 36 129 - 132 . .

Views

431

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

On-demand Peelable UV-curable Adhesives with Superior Bonding Strength: Rational Molecular Engineering of Cohesion-adhesion Synergy

Bioinspired Zinc-doped Nano Hydroxyapatite Reinforced Poly(lactic acid) Composites for Bone Repair

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

2026-9 Contents

Sliding Dynamics of Ring Chain on a Rod-Coil Block Copolymer in Rotaxane

Related Author

No data

Related Institution

No data

⁰