RESUMO
Acrylates (acrylic esters) are versatile monomers that are widely used in polymer formulations because of their highly reactive α,ß-unsaturated carboxyl structure. Commonly used acrylates such as butyl acrylate are known to emit a strong unpleasant odour, and the monomers are therefore potential off-odorants in acrylic polymers. However, up to now, the odour properties of structurally related acrylic esters have not been characterised in detail. To obtain deeper insights into the smell properties of different acrylates, we investigated the relationship between the molecular structure and odour thresholds as well as the odour qualities of 20 acrylic esters, nine of these synthesised here for the first time. The OT values of 16 acrylates fell within the range from 0.73 to 20 ng/Lair, corresponding to a high-odour activity. Moreover, sec-butyl acrylate and 2-methoxyphenyl acrylate showed even lower OT values of 0.073 and 0.068, respectively. On the other hand, the OT values of the hydroxylated acrylates 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate were 5-244 times higher than those of the other compounds, demonstrating that the presence of a hydroxyl group obviously favours odour inactivity.
RESUMO
Elastic therapeutic tapes are an important tool in the field of physical therapy and medicine. These tapes contain types of adhesive. However, sensory evaluations revealed the release of pronounced and irritating odors of the tapes. Negative odors were, amongst others, reported in elastic therapeutic tapes containing acrylic adhesives. In this study, the odor of four different tape samples was evaluated applying a descriptive analysis approach carried out by a trained sensory panel. Afterwards, the volatile compounds were recovered from the samples by solvent extraction and isolated by solvent-assisted flavor evaporation (SAFE). The obtained distillates were subsequently analyzed by gas chromatography-olfactometry (GC-O) and two-dimensional GC-O coupled with mass spectrometry (2D-GC-MS/O). To determine the most potent odorants in the distillates, odor extract dilution analyses (OEDA) were carried out. Thirty-one odorants were successfully identified using this approach, which were all described for the first time as odorants in tapes. Amongst the set of volatiles, unsaturated and saturated aldehydes were present, eliciting fatty, soapy, and citrus-like odor impressions, as well as a range of glue-like, moldy, and fruity smelling odor-active volatiles, such as 2-ethyl-1-hexanol, butyl benzoate, and 3-phenyltoluene. Based on their relative intensities, the concentrations of the glue-like smelling substances were determined: 2-ethyl-1-hexanol, present in all samples, was determined with concentrations ranging from 10 to 200 mg/kg in the investigated tapes.
Assuntos
Adesivos/química , Aldeídos/análise , Hexanóis/análise , Odorantes/análise , Compostos Orgânicos Voláteis/análise , Cromatografia Gasosa-Espectrometria de Massas/métodos , Humanos , Olfatometria/métodos , Modalidades de FisioterapiaRESUMO
Most children's toys on the market are primarily made out of plastic and other complex composite materials. Consumer complaints about offensive odors or irritating effects associated with toy products have increased in recent years. One example is the strongly perceivable negative odor reported for a particular series of toy swords. Characterizing the presence of contaminants, including those that have the potential to be deleterious to health, in such products is a significant analytical challenge due to the high baseline abundance of chemical constituents of the materials used in the products. In the present study, the nature of offensive odorants associated with toy sword products was examined by gas chromatography (GC). After initial sensory evaluations, the volatile compounds from the toy products were recovered using solvent extraction and solvent-assisted flavor evaporation. The extracts were analyzed using GC-olfactometry (GC-O) and two-dimensional GC-O coupled with mass spectrometry (GC-GC-MS/O). A total of 26 odor-active compounds, including aromatic hydrocarbons and phenols, were identified among numerous non-odorous volatile by-products. These substances also included polycyclic aromatic hydrocarbons, which were analyzed by GC-MS. Representative substances were naphthalene and 1,2-dihydronaphthalene that exhibited moldy, mothball-like odor impressions, and phenol derivatives with leather-like, phenolic, horse-stable-like smells. The odorants detected correlated with the assigned attributes from the sensory analyses. This study clearly shows that the detection and identification of such odorous contaminants can provide key indications of potentially harmful yet unknown substances in everyday products such as toys. Graphical abstract á .
Assuntos
Odorantes/análise , Olfatometria , Jogos e Brinquedos , Hidrocarbonetos Policíclicos Aromáticos/análise , Cromatografia Gasosa-Espectrometria de Massas , HumanosRESUMO
The still-rising global demand for plastics warrants the substitution of non-renewable mineral oil-based resources with natural products as a decisive step towards sustainability. Lignin is one of the most abundant natural polymers and represents an ideal but hitherto highly underutilized raw material to replace petroleum-based resources. In particular, the use of lignin composites, especially polyolefin-lignin blends, is currently on the rise. In addition to specific mechanical property requirements, a challenge of implementing these alternative polymers is their heavy odor load. This is especially relevant for lignin, which exhibits an intrinsic odor that limits its use as an ingredient in blends intended for high quality applications. The present study addressed this issue by undertaking a systematic evaluation of the odor properties and constituent odorants of commercially available lignins and related high-density polyethylene (HDPE) blends. The potent odors of the investigated samples could be attributed to the presence of 71 individual odorous constituents that originated primarily from the structurally complex lignin. The majority of them was assignable to six main substance classes: carboxylic acids, aldehydes, phenols, furan compounds, alkylated 2-cyclopenten-1-ones, and sulfur compounds. The odors were strongly related to both the lignin raw materials and the different processes of their extraction, while the production of the blends had a lower but also significant influence. Especially the investigated soda lignin with hay- and honey-like odors was highly different in its odorant composition compared to lignins resulting from the sulfurous kraft process predominantly characterized by smoky and burnt odors. These observations highlight the importance of sufficient purification of the lignin raw material and the need for odor abatement procedures during the compounding process. The molecular elucidation of the odorants causing the strong odor represents an important procedure to develop odor reduction strategies.