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1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC), is a building block that can be used in polymer science.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) has also shown to have synergistic flame retardancy properties.
Additive to plastics, especially to impart thermal stability.
CAS: 839-90-7
MF: C9H15N3O6
MW: 261.23
EINECS: 212-660-9
Synonyms
1,3,5-TRIS(2-HYDROXYETHYL) 1,3,5-TRIAZINE-2,4,6(1H,3H,6H)TRIONE;1,3,5-TRIS(2-HYDROXYETHYL)CYANURIC ACID;1,3,5-TRIS(2-HYDROXYETHYL)-HEXAHYDRO-S-TRIAZINE-2,4,6-TRIONE;1,3,5-TRIS(2-HYDROXYETHYL)ISOCYANURIC ACID;ISOCYANURIC ACID TRIS(2-HYDROXYETHYL) ESTER;TRIS(HYDROXYETHYL) ISOCYANURATE;1,3,5-tris(2-hydroxyethyl)isocyanurate;tris(beta-hydroxyethyl)isocyanurate
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is a white crystalline powder that is soluble in water, THF and hot lower alcohols.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is insoluble in other common organic solvents.
This symmetrical triol undergoes reactions typical of unhindered, primary hydroxyl groups.
Tris(2-hydroxyethyl) isocyanurate, often abbreviated as 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC), is a chemical compound with various industrial applications due to its unique properties.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC), commonly referred to as THEIC, is a symmetrical triol compound with the molecular formula C₉H₁₅N₃O₆.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) appears as a white crystalline powder that is soluble in water and certain organic solvents, such as tetrahydrofuran and hot lower alcohols, but insoluble in many common organic solvents.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is characterized by its trifunctionality, allowing it to participate in various
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is a chemical compound containing hydroxyl groups.
Three hydroxyethyl groups are attached to an isocyanurate ring, specifically to its nitrogen atoms.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) Chemical Properties
Melting point: 136-140 °C(lit.)
Boiling point: 526.7±45.0 °C(Predicted)
density: 1.498±0.06 g/cm3(Predicted)
vapor pressure: 0.001Pa at 50℃
Fp: 241℃
storage temp.: Store below +30°C.
solubility: 1150g/l
pka: 14.03±0.10(Predicted)
form: Solid
color: White to Off-White
PH: 7 (100g/l, H2O, 20℃)
Water Solubility: 572g/L at 20℃
Stability: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C9H15N3O6/c13-4-1-10-7(16)11(2-5-14)9(18)12(3-6-15)8(10)17/h13-15H,1-6H2
InChIKey: BPXVHIRIPLPOPT-UHFFFAOYSA-N
LogP: -1.63 at 23℃
CAS DataBase Reference: 839-90-7(CAS DataBase Reference)
EPA Substance Registry System: 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) (839-90-7)
Reactivity Profile
An organo-isocyanate.
Isocyanates and thioisocyanates are incompatible with many classes of compounds, reacting exothermically to release toxic gases.
Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat.
Acids and bases initiate polymerization reactions in these materials.
Some isocyanates react with water to form amines and liberate carbon dioxide.
Flame Retardant Properties:
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) exhibits inherent flame retardancy due to its unique chemical structure.
Research suggests its ability to decompose and release non-flammable gases when exposed to heat, potentially acting as a flame retardant additive in various materials.
Studies have explored incorporating 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) into polymers and textiles to enhance their flame resistance properties.
Biomedical Applications:
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC)'s biocompatibility and water solubility make it a potential candidate for drug delivery applications.
Research has investigated its use as a carrier molecule for encapsulating and delivering therapeutic drugs within the body.
Additionally, studies have explored 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC)'s potential as a crosslinking agent in hydrogels for biomedical applications.
Uses
Used in the manufacture of heat-resistant enameled wires and lacquers with excellent mechanical properties, various polyurethane plastics, water-soluble baking varnishes, unsaturated polyester resins, insecticides, plasticizers, dyes, pharmaceuticals and other organic synthetic intermediates.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is also used as a stabilizer for PVC to improve the processing temperature and performance of PVC.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is used as a monomer in special polyester resins.
Compared to conventional polyester resin monomers, 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) offers exceptional heat resistance due to its isocyanurate ring.
Furthermore, resins based on tris(2-hydroxyethyl)isocyanurate are highly resistant to solvents and simultaneously very flexible, making them particularly suitable for use in wire enamels.
A disadvantage of 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) is its high price compared to conventional resin monomers.
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) has diverse applications across multiple industries:
Coatings: Used as a monomer for producing thermosetting paints, magnet wire enamels, and electrical insulating varnishes.
Polymer Production: Acts as a crosslinking agent for rigid urethane foams and postforming laminating resins.
Flame Retardants: Incorporated into intumescent flame retardant systems for plastics like polypropylene to enhance thermal stability and fire resistance.
Intermediate in Synthesis: Serves as an intermediate for synthesizing dyes, agrochemicals, pharmaceuticals, and plasticizers.
Organic Synthesis:
1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC)'s reactive hydroxyl groups and cyclic structure make it a valuable intermediate in organic synthesis.
Researchers have utilized 1,3,5-Tris(2-hydroxyethyl)isocyanurate (THEIC) as a building block for synthesizing various functional molecules, including dyes, pharmaceuticals, and plasticizers.
