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


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.

1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione
Structure of 1,3,5-Tris(4-(tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione
Names
Preferred IUPAC name
1,3,5-Tris(4-(Tert-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione
Other names
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)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.049.980 Edit this at Wikidata
EC Number
  • 254-996-9
UNII
  • 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
    Key: InChIKey=XYXJKPCGSGVSBO-UHFFFAOYSA-N
  • 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
Properties
C42H57N3O6
Molar mass 699.933 g·mol−1
Appearance White solid
Density 1.15
Melting point 158 to 162 °C (316 to 324 °F; 431 to 435 K)
Boiling point 370 °C (698 °F; 643 K)
0.02 mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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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

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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

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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,[1] which makes it common choice in synthetic fibres (polyurethane, polyester and polyamide), particularly elastane.

References

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  1. ^ Vulic, Ivan; Vitarelli, Giacomo; Zenner, John M. (January 2002). "Structure–property relationships: phenolic antioxidants with high efficiency and low colour contribution". Polymer Degradation and Stability. 78 (1): 27–34. doi:10.1016/S0141-3910(02)00115-5.
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