Chromatographic Methods for the Determination of Polyfunctional Amines and Related Compounds Used as Monomers and Additives in Food Packaging Materials: A State‐of‐the‐Art Review

Paseiro-Cerrato, Rafael; Quirós, A. Rodrı́guez-Bernaldo de; Sendón, Raquel; Bustos, Juana; Santillana, María Isabel; Cruz, J.M.; Paseiro-Losada, P.

doi:10.1111/j.1541-4337.2010.00133.x

Cited by 24 publications

(6 citation statements)

References 91 publications

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“…The p K a increases with an increase in the amine basicity. Table gives p K a values of the five amines used in this work. , On the basis of our knowledge, the amines having a p K a value in the range of 5–9 are mainly tertiary aliphatic species, which are not suitable as a curing agent for epoxies. It appears that p K a > 9 is required for amines to properly react with CO 2 and to generate ammonium carbamate salt powders.…”

Section: Results and Discussionmentioning

confidence: 99%

Development of Epoxy Foaming with CO₂ as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Ren

et al. 2015

Ind. Eng. Chem. Res.

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Some commercially available amines used as curing agents for epoxy resins can capture CO2 to form ammonium carbamates, which represent a novel type of latent blowing and curing agent for epoxy foaming. The principles in the selection of suitable amines are critical for final applications. This work aimed to reveal these principles by screening and comparing the preparation, chemical structure and composition, and curing and foaming performance of several types of ammonium carbamates from typical amine curing agents. It is found that amines with pK a >9 are eligible to react with CO2 to form ammonium carbamates with a high yield. Furthermore, the amines should have rigid cyclic groups in their structures to form a solid ammonium carbamate powder, which can be easily mixed with epoxy resins. The curing rate of the amine should not be much faster than the decomposition of the carbamate to obtain epoxy foams with good pore morphology and mechanical performance.

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Section: Results and Discussionmentioning

confidence: 99%

Development of Epoxy Foaming with CO₂ as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Ren

et al. 2015

Ind. Eng. Chem. Res.

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“…DPBD belongs to fluorescent whitening agents; Uvitex OB is an optical brightener, both compounds act protecting the colour of plastic materials from adverse environmental conditions and aid to prevent yellowing and discoloration that polymers can suffer from under unfavorable conditions. Benzophenone, is a photoinitiator for UV-cured inks, commonly used for printing the external face of packaging [5].…”

Section: Introductionmentioning

confidence: 99%

Study of the Migration of Three Model Substances from Low Density Polyethylene into Food Simulant and Fruit Juices

2015

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In the present work, the migration of three chemicals, benzophenone, 1,4-diphenylbutadiene and Uvitex® OB from low-density polyethylene samples into the food simulant, 50% ethanol (v/v), was studied. The key parameters of the diffusion process, the partition and diffusion coefficients, were calculated by using a mathematical model based on Fick’s Second Law. As expected, the diffusion coefficients increased with temperature and the values obtained ranged between 3.87 × 10−11 and 1.00 × 10−8 cm2/s. Furthermore, the migration in different fruit juices was also evaluated and the results indicated that benzophenone migrated to a greater extent in comparison with the other two migrants in all beverages analyzed. To quantify the migrants, a high-performance liquid chromatographic method with a diode array detector (HPLC-DAD) was used. The separation was performed on an Ace 3 C18-HL column (30 × 3 mm, 3 μm particle size) and using a gradient elution system consisting of Milli-Q water and acetonitrile. The total analysis time did not exceed 8 min.

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“…In food packaging these resins are usually employed as inner coatings for cans (Paseiro-Losada et al 1998;Simal-Gándara et al 1998;Simal-Gándara 1999;Paseiro-Cerrato et al 2010). Besides, mXDA is one of the monomers (along with adipic acid) of PA MXD-6 (poly(m-xylylene adipamide)), which is a commercial polyamide (Mitsubishi, Japan), used as barrier layer to gases and water vapour (Robertson 2013).…”

Section: Introductionmentioning

confidence: 99%

Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity

Paseiro-Cerrato

Quirós

Sendón

et al. 2014

Food Additives & Contaminants: Part A

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It is a well-known fact that amines are not stable in food of a fatty nature. In this study the synthesis and characterisation of the products obtained as a result of the reaction of amines in a fatty medium are reported. Based on the well-known reactions among amines and acid and esters groups, two novel compounds were synthesised using m-xylylenediamine (mXDA), a primary diamine widely used as monomer in the manufacture of food contact materials and two fatty acids, oleic acid and palmitic acid, which occur in most fats. The resulting compounds were two molecules belonging to the family of fatty acid amides, dioleamide and dipalmitamide. A complete characterisation of both products was carried out employing several techniques such as infrared spectroscopy, (1)H- and (13)C-NMR spectroscopy, electron ionisation mass spectrometry, LC-MS/MS and UV spectrometry. The results obtained by the different techniques were well correlated. In the second part of the work, the formation of these compounds in real samples was evaluated. For this purpose a certain volume of olive oil was spiked with a known amount of mXDA. Olive oil was selected as a fatty medium since it is a widely consumed food and additionally is used as a fatty food simulant in migration studies of food contact materials. A method was developed to extract the fatty acid amides from the fatty matrix, which were then identified by LC-MS/MS. The toxicity of the synthesised compounds was predicted using a toxicity estimation software tool.

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Chromatographic Methods for the Determination of Polyfunctional Amines and Related Compounds Used as Monomers and Additives in Food Packaging Materials: A State‐of‐the‐Art Review

Cited by 24 publications

References 91 publications

Development of Epoxy Foaming with CO₂ as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Development of Epoxy Foaming with CO₂ as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Study of the Migration of Three Model Substances from Low Density Polyethylene into Food Simulant and Fruit Juices

Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity

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Chromatographic Methods for the Determination of Polyfunctional Amines and Related Compounds Used as Monomers and Additives in Food Packaging Materials: A State‐of‐the‐Art Review

Cited by 24 publications

References 91 publications

Development of Epoxy Foaming with CO2 as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Development of Epoxy Foaming with CO2 as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Study of the Migration of Three Model Substances from Low Density Polyethylene into Food Simulant and Fruit Juices

Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity

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Product

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Development of Epoxy Foaming with CO₂ as Latent Blowing Agent and Principle in Selection of Amine Curing Agent

Development of Epoxy Foaming with CO₂ as Latent Blowing Agent and Principle in Selection of Amine Curing Agent