Fluorinated epoxides as surface modifying agents of UV‐curable systems

Sangermano, Marco; Bongiovanni, Roberta Maria; Malucelli, Giulio; Priola, Aldo; Pollicino, Antonino; Recca, A.

doi:10.1002/app.12244

Cited by 53 publications

(49 citation statements)

References 16 publications

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“…At the air interface, all the films are hydrophobic ( Air Ͼ 90°). 48 There is a marked increase in Air for films based on III (124 -153°). Films based on III are also hazy.…”

Section: Contact-angle Analysismentioning

confidence: 98%

Crosslinking of 1,9‐bis[glycidyloxypropyl]penta‐ (1′H,1′H,2′H,2′H‐perfluoroalkylmethylsiloxane)s with α,ω‐diaminoalkanes: The cure behavior and film properties

Grunlan

Lee

Weber

2004

J of Applied Polymer Sci

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A series of nine films were prepared via phenol-catalyzed thermal crosslinking reactions of 1,9-bis-[glycidyloxypropyl]pentasiloxanes {1,9-bis[glycidyloxypropyl]decamethylpentasiloxane (I), 1,9-bis[glycidyloxypropyl]-3,5,7-tris(3Ј,3Ј,3Ј-trifluoropropyl)heptamethylpentasiloxane (II), and 1,9-bis[glycidyloxypropyl]-3,5,7-tris(1ЈH,1ЈH,2ЈH,, and 1,12-diaminododecane (c)]. The crosslink density was controlled by the choice of a-c. The cure behavior of I-III with a-c was studied with differential scanning calorimetry. The mechanical properties of the films were determined by dynamic mechanical thermal analysis. Their thermal stability was analyzed by thermogravimetric analysis. The surface properties of the films were evaluated with static contact-angle measurements. These films represented a novel class of epoxies with an unusual combination of properties: high flexibility (low glasstransition temperature), good thermal stability, and hydrophobic surfaces.

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“…At the air interface, all the films are hydrophobic ( Air Ͼ 90°). 48 There is a marked increase in Air for films based on III (124 -153°). Films based on III are also hazy.…”

Section: Contact-angle Analysismentioning

confidence: 98%

Crosslinking of 1,9‐bis[glycidyloxypropyl]penta‐ (1′H,1′H,2′H,2′H‐perfluoroalkylmethylsiloxane)s with α,ω‐diaminoalkanes: The cure behavior and film properties

Grunlan

Lee

Weber

2004

J of Applied Polymer Sci

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“…Fluorinated coatings have hydrophobicity, chemical stability, weathering resistance, low refractive indices, good release properties, low coefficients of friction, water impermeability, low surface free energies and non-stick properties [22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Coating Performance of UV-Curable Hybrid Polymers Containing 1H,1H,2H,2H-Perfluorooctyltriethoxysilane Coated on Aluminum Substrates

Çakır

2017

Coatings

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This study describes preparation and characterization of fluorine-containing organicinorganic hybrid coatings. The organic part consists of bisphenol-A glycerolate (1 glycerol/phenol) diacrylate resin and 1,6-hexanediol diacrylate reactive diluent. The inorganically rich part comprises trimethoxysilane-terminated urethane, 1H,1H,2H,2H-perfluorooctyltriethoxysilane, 3-(trimethoxysilyl) propyl methacrylate and sol-gel precursors that are products of hydrolysis and condensation reactions. Bisphenol-A glycerolate (1 glycerol/phenol) diacrylate resin was added to the inorganic part in predetermined amounts. The resultant mixture was utilized in the preparation of free films as well as coatings on aluminum substrates. Thermal and mechanical tests such as DSC, thermo-gravimetric analysis (TGA), and tensile and shore D hardness tests were performed on free films. Water contact angle, gloss, Taber abrasion test, cross-cut and tubular impact tests were conducted on the coated samples. SEM examination and EDS analysis was performed on the fractured surfaces of free films. The hybrid coatings on the aluminum sheets gave rise to properties such as moderately glossed surface; low wear rate and hydrophobicity. Tensile strength of free films increased with up to 10% inorganic content in the hybrid structure and this increase was approximately three times that of the control sample. As expected; the % strain value decreased by 17.3 with the increase in inorganic content and elastic modulus values increased by a factor of approximately 6. Resistance to ketone-based solvents was proven and an increase in hardness was observed as the ratio of the inorganic part increased. Samples which contain 10% sol-gel content were observed to provide optimal properties.

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“…18 The concentration of a photoinitiator, Irgacure 907, was adjusted to 5.0 wt % for mixtures of each base monomer with 16F-AC. The weight percentage (wt %) of 16F-AC in the UV-curable resins was changed in the range 027 wt %.…”

mentioning

confidence: 99%

“…17 16F-AC was chosen as the fluorinated reactive additive because of its good miscibility with the base monomers and according to the previous report that an outermost surface occupied by difluoromethyl groups shows a low surface free energy. 18 The concentration of a photoinitiator, Irgacure 907, was adjusted to 5.0 wt % for mixtures of each base monomer with 16F-AC. The weight percentage (wt %) of 16F-AC in the UV-curable resins was changed in the range 027 wt %.…”

mentioning

confidence: 99%

Surface Segregation of 1H,1H,9H-Hexadecafluorononyl Acrylate in Dimethacrylate Resin Films Cured by Exposure to Ultraviolet Light

et al. 2012

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The surface free energies of dimethacrylate resin films containing a fluorinated reactive additive, 1H,1H,9H-hexadecafluorononyl acrylate, cured by exposure to ultraviolet (UV) light, were investigated. Hansen's solubility parameter was useful for choosing a base monomer suitable for the fluorinated additive, which lowered the surface free energy of the cured resin film and decreased the release energy on demolding in UV nanoimprinting.Ultraviolet nanoimprint lithography (UV-NIL) is one of the promising technologies for the mass production of electrical, optical, and magnetic nanostructured devices.1,2 The practical use of UV-NIL mainly requires establishment of the basic science and technology for the elimination of resist pattern defects, improvement of throughput, and a reduction in the cost of fabricating a master silica mold. One approach to elongating the mold lifetime is to the reduce mechanical stress that the mold experiences during repeated demolding processes. The use of a silica mold modified with a release layer is one of the general approaches to decrease the demolding force.35 However, this method has the problem that resin components adhere partially to the modified mold surface during continuous demolding. 68 The demolding force can be decreased by using UV-curable resins containing fluorinated compounds, which lower the surface free energies of cured resin films.911 An organicinorganic resin pattern containing 1H,1H,2H,2H-perfluorooctyltriethoxysilane enabled continuous nanoimprinting as many as 50 times, and an 80-nm-wide channel transistor was made on a silicon substrate by subsequent dry etching. 12 Although there have been several studies on lowering the surface free energies of cured resins by searching for the most effective fluorinated additive to a certain resin, 13,14 general knowledge of what type of main monomer causes surface segregation of a certain fluorinated additive in a UV-curable resin is still lacking. In this communication, we demonstrated that Hansen's solubility parameter 15,16 was useful in searching for a suitable methacrylate monomer that decreased the surface free energy of a cured resin by adding 1H,1H,9H-hexadecafluorononyl acrylate (16F-AC).Glycerin 1,3-dimethacrylate (GDM) and 1,3-butanediol dimethacrylate (BDM) were used as the base monomers because of their similar chemical structures, in addition to their low viscosities, which are required for UV-NIL.17 16F-AC was chosen as the fluorinated reactive additive because of its good miscibility with the base monomers and according to the previous report that an outermost surface occupied by difluoromethyl groups shows a low surface free energy. 18 The concentration of a photoinitiator, Irgacure 907, was adjusted to 5.0 wt % for mixtures of each base monomer with 16F-AC. The weight percentage (wt %) of 16F-AC in the UV-curable resins was changed in the range 027 wt %. The chemical structures are shown in Figure 1. Thin films of each UV-curable resin, having a thickness of approximately 2.0¯m, were prepared by spinco...

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Fluorinated epoxides as surface modifying agents of UV‐curable systems

Cited by 53 publications

References 16 publications

Crosslinking of 1,9‐bis[glycidyloxypropyl]penta‐ (1′H,1′H,2′H,2′H‐perfluoroalkylmethylsiloxane)s with α,ω‐diaminoalkanes: The cure behavior and film properties

Crosslinking of 1,9‐bis[glycidyloxypropyl]penta‐ (1′H,1′H,2′H,2′H‐perfluoroalkylmethylsiloxane)s with α,ω‐diaminoalkanes: The cure behavior and film properties

Investigation of Coating Performance of UV-Curable Hybrid Polymers Containing 1H,1H,2H,2H-Perfluorooctyltriethoxysilane Coated on Aluminum Substrates

Surface Segregation of 1H,1H,9H-Hexadecafluorononyl Acrylate in Dimethacrylate Resin Films Cured by Exposure to Ultraviolet Light

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