Ultraviolet-curable optically clear resins using novel fluorinated imide-modified urethane acrylates

Ha, Yu‐Mi; Cho, Eunbee; Lim, Hyun‐Tae; Won, Jong Chan; Kim, Yun Ho; Kim, Yong Seok

doi:10.1016/j.mtcomm.2022.104370

Cited by 7 publications

(5 citation statements)

References 29 publications

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“…It can also observe the appearance of small NH group peaks at 3546 cm -1 suggesting that AEPO has reacted with isocyanates and shows that urethane linkage has formed [15]. C-F peak also present at 1011cm -1 that showed linkage between HDFDMA [16]. However, the existence of free isocyanate group at 2341 cm -1 suggested that the reaction was incomplete [14].…”

Section: Resultsmentioning

confidence: 94%

“…The disappearance of this peak shows the complete consumption of C=C crosslink with other monomers. In addition, the CF stretching can be observed at 1024 cm -1 that shows the successful of HDFDMA addition [16]. The weaker N-H peak at 3542cm -1 was observed as compared to Method 2 due to the lower reaction of AEPO with IPDI due to complex structure of AEPO.…”

Section: Clear Brownish Liquidmentioning

confidence: 88%

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Characterization of Fluoroacrylate Palm Oil Polyurethane (FPOPU) with Different Synthesis Methods Using Fourier-Transform Infra-Red (FTIR)

Mohamad Isa,

Binti Mustapha,

Bin Roslan

2024

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In this study, fluoroacrylate palm oil polyurethane (FPOPU) was synthesized with different synthesis methods. FPOPU was synthesized stepwise starting with the synthesis of acrylated epoxidized palm oil (AEPO) by a reaction of acrylic acid (AA) and triethylamine (TEA) as the catalyst. Then, palm oil polyurethane (POPU) was formed by the reaction of AEPO with isophorone diisocyanate (IPDI) and hydroxyethyl acrylate (HEA) as an end cap agent. POPU was further added with 1,6 hexanediol diacrylate (HDDA), trimethyloltripropane triacrylate (TMPTA), and heptafluorodecyl methyl-metacrylate (HDFDMA) monomers to form FPOPU. FPOPU synthesis methods were studied by manipulating the sequence of chemicals added, temperature, and mixing time of POPU. The FPOPU mixture was finally cast onto a silicone mold with 1 mm thickness and cured under UV radiation at 120 seconds. Based on the analysis, pre-mixed IPDI with HEA at 60°C for 15 min followed by the addition of AEPO at 60°C and further mixed for 3 hours (Method 2) shows the complete formation of the urethane chain. It is proven by the existence of NH peak at 3500 cm-1 and the disappearance of NCO peak at the range of 2200-2500 cm-1 indicating the NCO functional group has completely reacted with OH group in AEPO. The addition of fluorination also can be proved by the existence of CF stretching at 1012 cm-1. This study provides information regarding comparison between the synthesis method of FPOPU.

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Section: Resultsmentioning

confidence: 94%

Section: Clear Brownish Liquidmentioning

confidence: 88%

Characterization of Fluoroacrylate Palm Oil Polyurethane (FPOPU) with Different Synthesis Methods Using Fourier-Transform Infra-Red (FTIR)

Mohamad Isa,

Binti Mustapha,

Bin Roslan

2024

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“…38 1-(hydroxymethyl)-10-oxatricyclo [5.2.1.02.6]dec-8-ene-3,5-dione-2-aminoethanol (HODA) was obtained using the modified four-step technique. 3,25,39,40 Then HODA and dichloromethane were added to the round bottom flask equipped with a thermometer, magnetic stirrer, and dropper. After argon gas purging, hexamethylene diisocyanate (HDI) or isophorone diisocyanate (IPDI) was added dropwise over 1 h while stirring.…”

Section: Synthesis Of Uas With Built-in Diels-alder Structure (Ua-da)mentioning

confidence: 99%

“…[18][19][20][21][22] UA oligomers are obtained in a two-step process from diisocyanates (used in excess) and diols, resulting in a prepolymer containing terminal isocyanate groups, and then reacting the prepolymer with hydroxy acrylate. 1,[23][24][25][26] Consequently, these types of polymers have a favorable set of mechanical properties characteristic of polyurethanes 27 and partially exhibit optical properties typical of acrylates, 28 as well as the possibility of curing them with UV radiation. 29 Polyurethane acrylates (PUA) are characterized by distinctive structure, that is, the presence of "hard" segments (formed from urethane groups as well as acrylate groups) and "soft" segments (derived from polyester or aliphatic polyether chains).…”

Section: Introductionmentioning

confidence: 99%

Effect of hard segment chemistry and structure on the self‐healing properties of UV‐curable coatings based on the urethane acrylates with built‐in Diels–Alder adduct

Bednarczyk

Mozelewska

Nowak

et al. 2023

J of Applied Polymer Sci

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The development of new photoreactive resins to obtain smart coatings and enhance the self-healing (SH) properties of photoreactive resins has attracted great interest in the past few years, and the investigation of the relationship between phase structure and smart properties is necessary. Herein, four types of urethane acrylate resins with built-in DA structures with different hard segment structures, and a slight change in the length of the polyol soft segment were prepared. The hard segments were made of hexamethylene diisocyanate (HDI) with a linear structure and isophorone diisocyanate (IPDI) with an alicyclic structure, and the soft segments consisted of polyethylene glycols (PEG 400 and PEG 1000, respectively). The obtained resins were used to prepare polymer films that were cured using UV radiation. The coatings obtained in this way were tested for the influence of the polymer chain architecture on the kinetics of photopolymerization, the properties of the cured coatings, as well as the thermal characteristics and thermoreversibility performance of the cured coatings and their SH ability.

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“…Urethane methacrylate resins are widely used for hard coatings and adhesives because of their toughness, elongation, and high hardness. [1][2][3][4][5][6][7][8][9] Since urethane methacrylate is one of the UV-curable monomers, it is often used for 3D printer modeling and dental materials in recent years. [6][7][8][9][10][11][12] To further expand the applications of urethane methacrylate resins, academic and industry researchers are working to improve various physical properties commencing with heat resistance.…”

Section: Introductionmentioning

confidence: 99%

Stereospecific radical polymerization of methacrylate bearing oxazolidone structure and improvement of glass transition temperature of urethane methacrylate copolymers

Yoshinaga

Yoshida

2023

Journal of Polymer Science

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We synthesized the novel methacrylate monomer bearing an oxazolidone structure (M1) and performed radical polymerization of M1 by traditional procedures. The glass transition temperature (Tg) of the obtained polymer (P1) was a significantly high value compared to that of poly(methyl methacrylate) and typical poly(urethane methacrylate)s. The copolymers of M1 and monofunctional urethane methacrylate derived from 2‐hydroxyethyl methacrylate and phenyl isocyanate (M2) exhibited a linear rise of the Tg values depending on the composition ratio of M1. The NMR analysis and the estimation of monomer reactivity ratio and Q–e values suggested that the improvement of glass transition temperature resulted from a stereoregularity, meaning a syndiotacticity of the copolymers improved with increasing the composition ratio of M1. Furthermore, the thermal curing reaction of M1 or M2 with bifunctional urethane acrylate successfully proceeded, then the Tg value of the cured product from M1 was much higher than that from M2.

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Ultraviolet-curable optically clear resins using novel fluorinated imide-modified urethane acrylates

Cited by 7 publications

References 29 publications

Characterization of Fluoroacrylate Palm Oil Polyurethane (FPOPU) with Different Synthesis Methods Using Fourier-Transform Infra-Red (FTIR)

Characterization of Fluoroacrylate Palm Oil Polyurethane (FPOPU) with Different Synthesis Methods Using Fourier-Transform Infra-Red (FTIR)

Effect of hard segment chemistry and structure on the self‐healing properties of UV‐curable coatings based on the urethane acrylates with built‐in Diels–Alder adduct

Stereospecific radical polymerization of methacrylate bearing oxazolidone structure and improvement of glass transition temperature of urethane methacrylate copolymers

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