1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione

tert 1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione PAO-4 100.svg Structure of 1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione Tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinanetrione Chemical names Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-xylyl)methyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione 1,3,5-tris-[(3,5-di-tert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Trade names Cyanox 1790 (Syensqo) Irganox 3790 (BASF) Lowinox 1790 (SI Group) Songnox 1790 (Songwon) 84161 InChI=1S/C42H57N3O6/c1-22-16-31(40(7,8)9)34(46)25(4)28(22)19-43-37(49)44(20-29-23(2)17-32(41(10,11)12)35(47)26(29)5)39(51)45(38(43)50)21-30-24(3)18-33(42(13,14)15)36(48)27(30)6/h16-18,46-48H,19-21H2,1-15H3 InChIKey=XYXJKPCGSGVSBO-UHFFFAOYSA-N 3184256 40601-76-1 93221 254-996-9 253H13NWCQ C(N1C(=O)N(CC2=C(C)C(O)=C(C(C)(C)C)C=C2C)C(=O)N(CC3=C(C)C(O)=C(C(C)(C)C)C=C3C)C1=O)C4=C(C)C(O)=C(C(C)(C)C)C=C4C 42 57 3 6 White solid 1.15 158 to 162 370 0.02 mg/L 1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione (abbreviated here as Antioxidant 1790) is a speciality antioxidant used to stabilise plastics and synthetic fibres. Synthesis It can be synthesised in a 2-step manner. Firstly, 2,4-dimethyl-6-tert-butylphenol is reacted with formaldehyde and HCl (Blanc reaction) to generate a chloromethyl group in the less hindered meta position. This intermediate then reacts with cyanuric acid to give the desired product. Properties As each phenol group contains only a single t-butyl group they are considered to have low steric hindrance and thus high activity. Arranging three of these around an isocyanurate core gives a compound with a sufficiently high boiling point that it is not volatilised out of the plastic during plastic extrusion and moulding (up to 320 °C in the case of PA). The isocyanurate core also promotes a high level of crystallinity, which greatly reduces extraction of the antioxidant into water. Applications Although it is compatible with polyolefins Antioxidant 1790 is a fairly expensive antioxidant and it is primarily used in speciality applications. It has good compatibility with the engineering plastics, high activity and low colour formation,Vulic Ivan Vitarelli Giacomo Zenner John M. Structure–property relationships: phenolic antioxidants with high efficiency and low colour contribution Polymer Degradation and Stability January 2002 78 1 27–34 10.1016/S0141-3910(02)00115-5 which makes it common choice in synthetic fibres (polyurethane, polyester and polyamide), particularly elastane. See also Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate - related phenolic antioxidant with a cyanurate core References Category:Tert-butyl compounds Category:3-Hydroxyphenyl compounds Category:Triazines Category:Triketones Category:Phenol antioxidants