New phenylenediamine antiozonants for commodities based on natural and synthetic rubber.
For protection of elastomeric materials against ageing, antioxidants such as UV-stabilizers and antiozonants are used. Although historically N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD) was the only approved antiozonant in Germany, a range of other phenylene diamine antiozonants (excluding 6PPD) are permitted for use in rubber articles intended for repeat food-contact use in the US (FDA regulations chapter 21 Part 177.2600). The biggest disadvantage of 6PPD is its partial decomposition during the vulcanization leading to the formation of toxic primary aromatic amines (PAA), such as aniline and secondary aromatic amines (SAA). A number of new PPDs have been developed and patented, that due to their chemical structures, are far less soluble in aqueous solutions but a lot more soluble within the rubber matrix. They therefore show significantly less migration of PAA and SAA. These new antiozonants were investigated and compared to 6PPD using commercial rubber materials with a certain content of antiozonant with regard to their migration of PAA and SAA into three different food simulants. The lowest concentration of PAA and SAA in all food simulants was measured in the RU 997 stabilized elastomer. Due to this fact RU 997 was permitted as a new antiozonant for commodities based on rubber according to the Recommendation XXI 'Articles based on natural and synthetic rubber' of the Federal Institute for Risk Assessment (BfR). RU 997 therefore represents an alternative for 6PPD with less migration of aromatic amines.
Krüger
R H
RH
Fedral Institut for Materials Research and Testing, Berlin, Germany. Rita.Krueger@bam.de
Boissiére
C
C
Klein-Hartwig
K
K
Kretzschmar
H-J
HJ
D000588:Amines / Q000737:chemistry; D020724:Elastomers / Q000737:chemistry; D004781:Environmental Exposure / Q000009:adverse effects; D005506:Food Contamination; D018857:Food Packaging; D006801:Humans; D010126:Ozone / Q000037:antagonists & inhibitors; D010655:Phenylenediamines / Q000737:chemistry; D012408:Rubber; D012995:Solubility; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Q000379:methods; D013185:Squalene / Q000737:chemistry
D000588:Amines; D020724:Elastomers; D010655:Phenylenediamines; D010126:Ozone; D013185:Squalene; D012408:Rubber; C016096:N-(1,3-dimethylbutyl)-N'-phenyl-1,4-phenylenediamine