Isolation and identification of some unknown substances in disposable nitrile-butadiene rubber gloves used for food handling

• Published in: Food additives and contaminants Vol. 19; no. 11; pp. 1097 - 1103
• Main Authors: Mutsuga, M., Wakui, C., Kawamura, Y., Maitani, T.
• Format: Journal Article
• Language: English
• Published: London Taylor & Francis Group 01.11.2002; Taylor & Francis
• Subjects: 1,4-DIONE-2,5-BIS(1,1-DIMETHYLPROPYL) Cyclohexadiene; 2,4,6-TRIS(1,1,3,3-TETRAMETHYLBUTYL)PHENOL; Applied sciences; Biological and medical sciences; Disposable Equipment; Elastomers; Exact sciences and technology; Food Handling - methods; Food industries; Food toxicology; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; Gc/MS; Gloves, Protective; Magnetic Resonance Spectroscopy; Mass Spectrometry; Nitrile-BUTADIENE Rubber Gloves; Nmr; Organic Chemicals - isolation & purification; Polymer industry, paints, wood; Properties and testing; Rubber - chemistry; Technology of polymers; Testing and control; Glove; Migration; Quality control; Contact interaction; Polymer; Isolation; Identification; Chemical diffusion; Nitrile rubber; Chemical contamination
• ISSN: 0265-203X; 1464-5122
• DOI: 10.1080/02652030210151886

In Japan, disposable gloves made from nitrile-butadiene rubber (NBR) are frequently used in contact with foods. In a previous paper, we investigated substances migrating from various gloves made of polyvinyl chloride, polyethylene, natural rubber and NBR. Zinc di-n-butyldithiocarbamate (ZDBC), diethyldithiocarbamate (ZDEC) used as vulcanization accelerators, di(2-ethylhexyl)phthalate (DEHP) used as a plasticizer and many unknown compounds that migrated from NBR gloves into n-heptane were detected by GC/MS. In this paper, six unknown compounds were obtained from one kind of NBR glove by n-hexane extraction and each was isolated by silica gel chromatography. From the results of NMR and mass spectral analysis of the six unknown compounds, their structures are proposed as 1,4-dione-2,5-bis(1,1-dimethylpropyl)cyclohexadiene (1), 2-(1,1-dimethylethyl)-4-(1,1,3,3-tetra methylbutyl)phenol (2), 2,6-bis(1,1-dimethylethyl)-4-(1,1,3,3-tetramethylbutyl)phenol (3), 2,4-bis(1,1,3,3-tetramethylbutyl)phenol (4), 2-(1,1-dimethylethyl)4,6-bis(1,1,3,3-tetramethylbutyl)phenol (5) and 2,4,6-tris(1,1,3,3-tetramethylbutyl)phenol (6). Compound 1 was observed in five of the seven kinds of NBR gloves, and compounds 2-4 and 6, which are not listed in Chemical Abstract (CA), were present in four kinds of gloves.