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

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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-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
  • 1,3,5-tris--1,3,5-triazinane-2,4,6-trione

Trade names
  • Cyanox 1790 (Syensqo)
  • Irganox 3790 (BASF)
  • Lowinox 1790 (SI Group)
  • Songnox 1790 (Songwon)
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.049.980 Edit this at Wikidata
EC Number
  • 254-996-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,19-21H2,1-15H3Key: InChIKey=XYXJKPCGSGVSBO-UHFFFAOYSA-N
SMILES
  • 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
Chemical formula C42H57N3O6
Molar mass 699.933 g·mol
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)
Solubility in water 0.02 mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

See also

References

  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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