Eco-friendly UV-curable pressure sensitive adhesives containing acryloyl derivatives of monosaccharides and their adhesive performances

Baek, Seung-Suk; Hwang, Seok‐Ho

doi:10.1016/j.ijadhadh.2016.06.002

Cited by 25 publications

(16 citation statements)

References 22 publications

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“…Relatively rarely the photopolymerization method is used to obtain a liquid polymer or polymer solutions. Admittedly, in the last decade several publications have been published ‘regarding the method of obtaining acrylate syrups via the photoinduced polymerization process that occurs in large amounts of monomers’ mixture and with a mechanical mixing [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. Obtained products were mainly used as transparent pressure-sensitive adhesives.…”

Section: Introductionmentioning

confidence: 99%

Free-Radical Bulk-Photopolymerization Process as a Method of Obtaining Thermally Curable Structural Self-Adhesive Tapes and Effect of Used Type I Photoinitiators

2020

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A new fabrication method for thin (120 µm) thermally curable structural self-adhesive tapes (SATs) was demonstrated by utilizing a series of acrylic syrups (ASs) modified using Bisphenol A-based liquid epoxy resin. The acrylic syrups containing poly(butyl acrylate-co-butyl methacrylate-co-glycidyl methacrylate-co-2-hydroxyetyl acrylate-co-4-acryloyloxy benzophenone) were synthesized via free-radical bulk-photopolymerization (FRBP) process. Influence of different type I radical photoinitiators (PIs), i.e., α-hydroxyalkylphenones (HPs), acylphosphine oxides (APOs) and its mixtures (HPs/APOs and APO/APO) on selected physico-chemical features of obtained ASs was studied. It turned out that APO-type PIs are more effective in the FRBP process (NMR studies). Self-adhesive tests of SATs revealed that the monomers’ conversion in ASs have a significant influence on adhesion and tack. Moreover, the polymer structures formed at the UV cross-linking stage of SATs significantly affect the cross-linking degree of SATs during thermal curing (differential scanning calorimetry method). The highest values of overlap shear strength were achieved by SATs based on ASs with monomers’ conversion on the level 50–60%.

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Section: Introductionmentioning

confidence: 99%

Free-Radical Bulk-Photopolymerization Process as a Method of Obtaining Thermally Curable Structural Self-Adhesive Tapes and Effect of Used Type I Photoinitiators

2020

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“…In general, the monomer yield/carbohydrate conversion tends to be higher for enzymatic catalysis 12,[23][24][25][26][27][28][29][30][31][32][33][34][35][36] than for the chemical route, 13,[17][18][19][37][38][39][40][41][42] however, high yields in the carbohydrate functionalization can also be achieved using some chemical routes. 13,21,39,42 Moreover, Candida Antarctica lipase B (EC 3.1.1.3), commercially available in a supported form under the name Novozym ® 435, is widely used in the functionalization of carbohydrates in organic media, including the enzymatic-catalyzed carbohydrate (meth)acrylation. 12,[25][26][27][28][29]43 Lipase selectivity for (trans)esterification can be determined by the hydroxyl reactivity.…”

Section: Introductionmentioning

confidence: 99%

“…Table S1 (available in the Supporting information) summarizes the main results reported in the literature regarding the functionalization of glucose and fructose with polymerizable groups using both the chemical and enzymatic (lipase and protease) routes. In general, the monomer yield/carbohydrate conversion tends to be higher for enzymatic catalysis than for the chemical route, however, high yields in the carbohydrate functionalization can also be achieved using some chemical routes . Moreover, Candida Antarctica lipase B (EC 3.1.1.3), commercially available in a supported form under the name Novozym® 435, is widely used in the functionalization of carbohydrates in organic media, including the enzymatic‐catalyzed carbohydrate (meth)acrylation .…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Perin

Felisberti

2018

J of Chemical Tech & Biotech

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BACKGROUND Carbohydrates are important renewable raw materials and their modification by enzymatic reactions with polymerizable groups is of great importance due the possibility of production of polymers with properties for biomedical applications. In this study, D‐fructose‐ and D‐glucose‐based monomers were prepared by enzymatic reactions and structurally characterized. Moreover, hydrogels based on poly(methacryloyl‐D‐fructose) were also prepared and characterized. RESULTS The conversions of 99% and 34% for D‐fructose and D‐glucose, respectively, were achieved using 2,2,2‐trifluoroethyl methacrylate as the methacrylic donor and commercial lipase Novozyme® 435 (EC 3.1.1.3) as enzymatic catalyst in t‐butanol. The molar ratios of D‐fructose and D‐glucose mono‐ and dimethacrylate were 57/43 and 87/13, respectively. These monomers are an isomeric mixture related to the tautomeric equilibrium of the carbohydrates in solution. Methacryloyl‐D‐fructose was polymerized in the presence of a controlled amount of ethyleneglycol dimethacrylate as crosslinker achieving hydrogels with different crosslinking densities which are mechanically stable when subject to compression–decompression cycles and have a high water swelling capability. CONCLUSION The combination of 2,2,2‐trifluoroethylmethacrylate and Novozym® 435 in a heterogeneous media lead to the continuous carbohydrate solubilization and reaction with the formation of carbohydrates‐based monomers. The control of the monomer functionality enables the synthesis of hydrogels with different crosslinking densities that tune their properties. © 2017 Society of Chemical Industry

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“…Figure 2 shows the thermal decomposition temperature ( T d ) of hydrophilic acrylic PSA film. The temperature of acrylic PSA films was raised to 600 °C; all acrylic PSA films decomposed in three -steps [ 36 , 37 ]. The first weight loss occurred below 300 °C.…”

Section: Resultsmentioning

confidence: 99%

Change of Characterization and Film Morphology Based on Acrylic Pressure Sensitive Adhesives by Hydrophilic Derivative Ratio

et al. 2020

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Hydrophilic acrylic pressure-sensitive adhesives (PSAs) were synthesized by controlling the contents of 2-ethylhexyl acrylate (EHA), isobornyl acrylate (IBOA), and 2-hydroxyethyl acrylate (HEA); especially, the characteristic change of the HEA content was analyzed. Surface contact angle of acrylic PSA film decreased from 77.87° to 70.23° in the case of Acryl-2 to Acryl-8 (below HEA 10 wt %). However, the surface contact angle of Acryl-10 to Acryl-40 (HEA 10 wt % to 40 wt %) increased up to 92.29°, indicating hydrophobicity. All acrylic PSA films showed high adhesive force above 1800 gf/25 mm. According to X-ray diffraction (XRD) measurement, hydrophilic acrylic PSAs exhibited amorphous property and it was confirmed that the morphology of acrylic PSA film was significantly affected by the flexibility of the polymer chain and the strength of hydrogen bonding. The affinity with hydrophilic materials for acrylic PSA films was evaluated by T-type peel test, confirming that the affinity with hydrophilic materials is determined by the hydrophilicity of the acrylic PSA film. The synthesized acrylic PSA film is non-toxic regardless of the hydrophilicity.

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Eco-friendly UV-curable pressure sensitive adhesives containing acryloyl derivatives of monosaccharides and their adhesive performances

Cited by 25 publications

References 22 publications

Free-Radical Bulk-Photopolymerization Process as a Method of Obtaining Thermally Curable Structural Self-Adhesive Tapes and Effect of Used Type I Photoinitiators

Free-Radical Bulk-Photopolymerization Process as a Method of Obtaining Thermally Curable Structural Self-Adhesive Tapes and Effect of Used Type I Photoinitiators

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

Change of Characterization and Film Morphology Based on Acrylic Pressure Sensitive Adhesives by Hydrophilic Derivative Ratio

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