Fluorinated Oligomers and Polymers in Photopolymerization

Vitale, Alessandra; Bongiovanni, Roberta Maria; Améduri, Bruno

doi:10.1021/acs.chemrev.5b00120

Cited by 208 publications

(125 citation statements)

References 252 publications

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“…Proton nuclear magnetic resonance ( 1 H-NMR) spectra were recorded on a UAVANCEIII 400 MHz spectrometer (Santa Clara, CA, USA). All spectra were collected at room temperature with a 0.5% (w/v) sample solution in CDCl 3 or DMSO-d 6 . During the spectra collecting, zg45 pulse sequence was used and 24 scans were performed for each sample.…”

Section: Characterizationmentioning

confidence: 99%

“…Over the past few years, fluoropolymers [1][2][3][4] have attracted much attention due to their many advantages, such as weather resistance, heat resistance, and solvent resistance [5,6]. As the C-F bonds are particularly strong (bond energy of 485 kJ mol −1 ) and the fluorine atoms exhibit low polarizability and strong electronegativity [7], polymers containing a significant fraction of fluorine atoms usually possess excellent chemical and thermal stability [8].…”

Section: Introductionmentioning

confidence: 99%

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Preparation of UV-Curable Low Surface Energy Polyurethane Acrylate/Fluorinated Siloxane Resin Hybrid Coating with Enhanced Surface and Abrasion Resistance Properties

et al. 2020

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Low surface energy coatings have gained considerable attention due to their superior surface hydrophobic properties. However, their abrasion resistance and sustainability of surface hydrophobicity are still not very satisfactory and need to be improved. In this work, a series of utraviolet (UV)-curable fluorosiloxane copolymers were synthesized and used as reactive additives to prepare polyurethane acrylate coatings with low surface energy. The effect of the addition of the fluorinated graft copolymers on the mechanical durability and surface hydrophobicity of the UV-cured hybrid films during the friction-annealing treatment cycles was investigated. The results show that introducing fluorosiloxane additives can greatly enhance surface hydrophobicity of the hybrid film. With addition of 2 wt.% fluorosiloxane copolymers, the water contact angle (WCA) value of the hybrid film was almost tripled compared to that of the pristine PU film, increasing from 58 • to 144 • . The hybrid film also showed enhanced abrasion resistance and could withstand up to about 60 times of friction under a pressure of 20 kPa. The microstructure formed in the annealed film was found to contribute much to achieve better surface hydrophobicity. The polyurethane acrylate/fluorinated siloxane resin hybrid film prepared in this study exhibits excellent potential for applications in the low surface energy field.Especially, some pioneering studies demonstrated that the robust and self-healing ability of the fluorinated materials contribute significantly to the performance of superhydrophobic coatings. For example, Lin et al. [15] prepared superhydrophobic fabrics under 12 KPa and 28,000 cycles of abrasion with wool felt by using a fluoroalkyl silane and crosslinked polydimethylsiloxane (PDMS). Their results showed that the water contact angle of the fabrics remained above 150 • , indicating that the superhydrophobic surface character was retained. They also utilized fluorinated-decyl polyhedral oligomeric silsesquioxane (FD-POSS) and hydrolyzed fluorinated alkyl silane (FAS) to prepare superhydrophobic fabrics, which still exhibited superhydrophobic surface even under ten plasma-and-heat cycles [16]. Zhang et al. [17] combined thiol-ene fluorinated siloxane (T-FAS) and hydrophobic fumed silica nanoparticles to prepare superhydrophobic coatings that could withstand approximately 100 abrasion cycles at 45 KPa [18]. It should be noted that, in these examples, the materials were surface-modified materials rather than pure fluoropolymers.Incorporation of fluorinated groups into acrylate copolymers could bring several desirable properties to the polyacrylate coatings. Depending on their chain length, the contribution of the introduced fluoroalkyl-containing moieties to the material surface properties can be tailored. If the molecular chain of the moieties are too short, they may be buried within the polymer matrix, thus mitigating their contribution [19]. In this aspect, Koji Honda et al. [9] studied the effects of side chain length on the molecular ag...

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Section: Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of UV-Curable Low Surface Energy Polyurethane Acrylate/Fluorinated Siloxane Resin Hybrid Coating with Enhanced Surface and Abrasion Resistance Properties

et al. 2020

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“…The development of synthetic methods to prepare semifluorinated polymers is of great interest because these materials often possess interesting characteristics,s uch as high hydrophobicity,t unable lipophilicity,a nd improved thermal and chemical stability. [1,2] As ar esult, av ariety of methods have been developed for the preparation of such polymers. [3] Controlled/living radical polymerization (CRP), [3a] which enables the operationally simple polymerization of semifluorinated (meth)acrylates,isamong the most useful synthetic methods.…”

Section: Organocatalyzed Photocontrolled Radical Polymerization Of Sementioning

confidence: 99%

Organocatalyzed Photocontrolled Radical Polymerization of Semifluorinated (Meth)acrylates Driven by Visible Light

et al. 2017

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Fluorinated polymers are important materials that are widely used in many areas.Herein, we report the development of ametal-free photocontrolled radical polymerization of semifluorinated (meth)acrylates with an ew visible-lightabsorbing organocatalyst. This method enabled the production of av ariety of semifluorinated polymers with narrowm olarweight distributions from semifluorinated trithiocarbonates or perfluoroalkyl iodides.T he high performance of "ON/OFF" control and chain-extension experiments further demonstrate the utility and reliability of this method. Furthermore,t o streamline the preparation of semifluorinated polymers,ascalable continuous-flowapproach has been developed. Given the broad interest in fluorinated materials and photopolymerization, we expect that this method will facilitate the development of advanced materials with unique properties.The development of synthetic methods to prepare semifluorinated polymers is of great interest because these materials often possess interesting characteristics,s uch as high hydrophobicity,t unable lipophilicity,a nd improved thermal and chemical stability. [1,2] As ar esult, av ariety of methods have been developed for the preparation of such polymers. [3] Controlled/living radical polymerization (CRP), [3a] which enables the operationally simple polymerization of semifluorinated (meth)acrylates,isamong the most useful synthetic methods.[3] Fore xample,a tom-transfer radical polymerization (ATRP) [4] and its variants, [5] reversible addition-fragmentation chain transfer (RAFT) polymerization, [6] and nitroxide-mediated polymerization (NMP; [7] Scheme 1A,t op) have shown promising results for the preparation of precisely fluorinated materials.H owever,i n contrast to the CRP of nonfluorinated monomers, [4a,6a, 7a] most methods suffer from one or several of limitations,i ncluding 1) decreased control over molecular-weight distribution () at high conversion;2 )the use of af luorinated solvent; 3) undesired side reactions (e.g.,t ransesterification);o r 4) the use of am etal catalyst. Furthermore,c ontrol of the polymerization of semifluorinated monomers with an external stimulus, [8] such as visible light, has rarely been possible.[5]Recently,p hotoredox catalysis has found widespread application in ATRP, [9] RAFT/iniferter polymerization, [10] ring-opening metathesis polymerization, [11] and cationic polymerization, [12] thus providing arange of photo-CRP methods with excellent spatiotemporal control over chain growth. [13] Forthese processes,(meth)acrylates,acrylamides,and styrene derivatives are the most frequently investigated monomers. [13] Hawker and co-workers recently reported the precise synthesis of semifluorinated poly(meth)acrylates from activated alkyl bromides by the copper-catalyzed photo-ATRP method.[5] In their study,ametal catalyst and UV light were used to ensure efficient polymerization. Additionally,asemifluorinated tertiary alcohol solvent was required to suppress the transesterification.[5] Am etal-free method usi...

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“…11 When these compounds are added to its structure uorine atoms or CF 3 substituents, some properties are improved, such as oil and water repellences, refractive index, dielectric constant and thermal resistance. 12,13 Fluorinated acrylates and methacrylates are unsaturated esters that are used to develop a family of uorinated compounds [14][15][16][17][18] that have brought a greater interest in their application in various industries and research elds, such as 2,2,2-tri-uoroethylmethacrylate (CH 3 CH 2 C(O)OCH 2 CF 3 ) that has been used as a copolymer in stone monument coatings in Italy, since it prevents cyclization reactions. 19 Another example is the use of these uorinated unsaturated esters (UEF) in the area of medicine, with the application of relatively low doses of PFC emulsion (peruorinated chemicals) to maintain tissue oxygenation, which means that the autologous blood (blood transfusion) can be preserved and reinfused in the patient towards the end of the surgery, or in the postoperative period, as necessary, allowing surgery to begin at a reduced cell volume, reducing cell loss during subsequent bleeding.…”

Section: Introductionmentioning

confidence: 99%

Degradation of a series of fluorinated acrylates and methacrylates initiated by OH radicals at different temperatures

et al. 2020

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Fluorinated Oligomers and Polymers in Photopolymerization

Cited by 208 publications

References 252 publications

Preparation of UV-Curable Low Surface Energy Polyurethane Acrylate/Fluorinated Siloxane Resin Hybrid Coating with Enhanced Surface and Abrasion Resistance Properties

Preparation of UV-Curable Low Surface Energy Polyurethane Acrylate/Fluorinated Siloxane Resin Hybrid Coating with Enhanced Surface and Abrasion Resistance Properties

Organocatalyzed Photocontrolled Radical Polymerization of Semifluorinated (Meth)acrylates Driven by Visible Light

Degradation of a series of fluorinated acrylates and methacrylates initiated by OH radicals at different temperatures

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