Synthesis of tung oil–diacrylate copolymers via the Diels‐Alder reaction and properties of films from the copolymers

Trumbo, David L.; Mote, B. E.

doi:10.1002/app.1343

Cited by 26 publications

(19 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For films containing tung oil, a reduction of elongation from 8.3 to 2.4 % was observed and attributed to total fatty acid content of up to 80 % poly unsaturated fatty acids such as a-eleostearic acid, 15 % oleic acid and only 5 % saturated acids (Trumbo and Mote 2001). The high content of triple unsaturated conjugated acids play an important role in the selfpolymerization of tung oil under temperature, ultraviolet light and presence of compared to cedar wood essential oils with negligible fatty acid contents oxygen (Li and Larock 2000).…”

Section: Mechanical Properties Of the Filmsmentioning

confidence: 94%

“…Span 80 is a non-ionic surfactant also known as sorbitan monooleate or oleate with band at 3300-2900 cm -1 from hydroxyl, methylene and methyl CH stretching. The addition of CWO or tung oil into SBL film resulted in the appearance of two new bands at 1741 and 1463 cm -1 from carbonyl groups (C=O) associated with esters, carboxylic, carboxylates and double bonds from polyunsaturated palmitic, stearic acid, linoleic fatty components of tung oil (Pereda et al 2010;Trumbo and Mote 2001); sesquiterpenes alcohol, including cedrol, widdrol, sesquiterpenes such as cedrene, thujopsene from CWO (Kamatou et al 2010;Panten et al 2004). The increase in intensity of bands at 2927, 2866, 1463, and 1236 cm -1 from methylene and methyl groups was observed with increase of the amount of oils, clearly confirming their origin from eleostearic and oleic acid from tung oil as well as CWO terpenes.…”

Section: Mechanical Properties Of the Filmsmentioning

confidence: 99%

See 1 more Smart Citation

Antimicrobial activity of sugar beet lignocellulose films containing tung oil and cedarwood essential oil

Shen

Kamdem

2015

Cellulose

View full text Add to dashboard Cite

Several studies have been reported on the use of cellulose, lignocellulose, chitin and other biological macromolecules for food packaging. One of the major drawbacks limiting their wide uses is their limited antimicrobial and water vapor barrier properties. In this study, cedarwood (Thuja occidentalis) essential oil (CWO), known to contain terpenes, polyphenols and tung oil, known to contain fatty acids, were used as additives to improve water vapor barrier, antimicrobial, and physical properties of laboratory cast lignocellulose films. Physicochemical and mechanical properties were tested to evaluate the impact of the addition of oils in the films formulations. The addition of 15 % CWO and tung oils improved water vapor permeability by more than 25 % as also evidenced by the increase of contact angle between water and film by 134 % from 38.98°to 89.36°with 15 % tung oil. FTIR was used to monitor the presence of hydrophobic groups at 1463 and 1741 cm -1 from the oil on the film spectra confirming the improvement of film hydrophobicity from oils interactions. However, the addition of 15 % hydrophobic oils promoted a significant decrease in tensile properties of films (p B 0.05) by 40 % for CWO and 32 % for tung oil, respectively, due to a partial incompatibility between hydrophilic lignocellulose and hydrophobic oils. The use of a tailored coupling agent to reduce the incompatibility and to improve the load charge transfer between hydrophobic and hydrophilic group might reduce the decrease of the tensile properties with the addition of hydrophobic compounds. No significant difference (p [ 0.05) was observed on the thermal stability of films using TGA. The antimicrobial effects of lignocellulose films against bacteria namely Listeria innocua, Escherichia coli, and Salmonella enterica was tested by disk inhibition zone method and showed an improvement with the addition of 5 % CWO in the film. The Microbe Growth Index of the lignocellulose cellulosic films containing 20 % w/w of CWO decreases by 80 %. CWO and tung oil are good candidates to control microbial growth and water vapor permeability in flexible films. Future work will focus on the olfactory and tensile properties for applications in food packaging.

show abstract

Section: Mechanical Properties Of the Filmsmentioning

confidence: 94%

Section: Mechanical Properties Of the Filmsmentioning

confidence: 99%

Antimicrobial activity of sugar beet lignocellulose films containing tung oil and cedarwood essential oil

Shen

Kamdem

2015

Cellulose

View full text Add to dashboard Cite

show abstract

“…Tung oil, main constituent a glyceride of eleostearic acid with a conjugated triene structure, is readily available as a major product from the seeds of the tung tree. The high unsaturation and conjugation of the C@C bonds in tung oil makes it a high chemical reactivity with styrene, 15 divinylbenzene, 16 acrylates, 17 or maleic anhydride. 18 Therefore, we try to introduce the flexible chains into rosins by modifying rosin acid with tung oil before esterification.…”

Section: Introductionmentioning

confidence: 99%

Preparation and properties of glycerin ester of tung oil modified rosin

Ma¹,

Zhang

et al. 2013

J of Applied Polymer Sci

View full text Add to dashboard Cite

Tung oil modified rosins (TR) were prepared by reaction rosin with different amount of tung oil via Diels-Alder addition reaction and further used in the formulation of glycerin ester of tung oil modified rosins (GTR) with flexible characteristics. The effects of the amount of tung oil on the bromine value, molecular weight, thermostability, physical, and tackifying properties of GTRs were studied. The results showed that the bromine value of GTRs decreased and molecular weight of GTRs increased with the increase in the amount of tung oil. Meanwhile, increasing the amount of tung oil resulted in a significant decrease in both the softening points and viscosities of GTRs, but a slight increase in the thermostability of GTRs due to the incorporation of the flexible fatty chains into the rigid hydrophenanthrene units in rosins. Applied in PU adhesive as tackifier, the increase of the flexible chains content in GTRs led to an increase first and then decrease in both the miscibility of GTRs with PU and the T-peel strength of adhesives. The elongation at break of films increased monotonously, but their tensile strengths increased first and then decreased with increasing the flexible chains content in GTRs. GTRs with desired properties were prepared when the tung oil/rosin weight ratios were in the range from10/100 to 40/100.

show abstract

“…It is well known that tung-oil fatty acids can undergo a Diels-Alder reaction easily with a dienophile because of the conjugated double bonds. 13 The Diels-Alder reaction has been successfully used to synthesize tung-oil alkyds 12 and styrene-tung-oil resins.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and properties of acrylate‐modified tung‐oil waterborne insulation varnish

Wang

She

et al. 2014

J of Applied Polymer Sci

View full text Add to dashboard Cite

An acrylate-modified tung-oil waterborne insulation varnish was synthesized from tung oil, maleic anhydride, and acrylates via a Diels-Alder reaction and free-radical polymerization, and the varnish could be solidified at a relatively low temperature with blocked hexamethylene diisocyanate as a curing agent. The resulting films were characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, and differential scanning calorimetry. The insulation properties (electrical insulation strength, volume resistivity, and surface resistivity) of the varnish films were tested, and the resistances of films to salted water were evaluated. With an increase in the maleic anhydride content, the thermal stability of the film was improved, whereas the electrical insulation strength, volume resistivity, and surface resistivity decreased. The electrical insulation strength of the film after it was immersed in the NaCl solution was lower than that in dry state, and it decreased as the immersed time was prolonged. In particular, the electrical insulation strength loss of the film increased significantly at maleic anhydride contents beyond 25 wt %. Furthermore, the hardness of the film increased with increasing methyl methacrylate/N-butyl acrylate ratio, whereas the flexibility and adhesion of film decreased to a certain degree at the same time.

show abstract

Synthesis of tung oil–diacrylate copolymers via the Diels‐Alder reaction and properties of films from the copolymers

Cited by 26 publications

References 4 publications

Antimicrobial activity of sugar beet lignocellulose films containing tung oil and cedarwood essential oil

Antimicrobial activity of sugar beet lignocellulose films containing tung oil and cedarwood essential oil

Preparation and properties of glycerin ester of tung oil modified rosin

Synthesis, characterization, and properties of acrylate‐modified tung‐oil waterborne insulation varnish

Contact Info

Product

Resources

About