3779-63-3

Basic information

• Product Name: (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene) isocyanate
• Synonyms: (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene) isocyanate;1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(6-isocyanatohexyl)-;HEXAMETHYLENEDIISOCYANATEISOCYANURATE;HDIISOCYANURATE;1,6-HEXAMETHYLENEDIISOCYANATEISOCYANURATE;TRISHEXAMETHYLENE TRIISOCYANATE);[(1,2,3,4,5,6-Hexahydro-2,4,6-trioxo-1,3,5-triazine-1,3,5-triyl)trishexamethylene]triisocyanate;1,3,5-Tris(6-isocyanatohexyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
• CAS NO: 3779-63-3
• Molecular Formula: C₂₄H₃₆N₆O₆
• Molecular Weight: 505.58718
• EINECS: 223-242-0
• Mol File: 3779-63-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 648.2°Cat760mmHg
• Flash Point: 345.8°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.001Pa at 20℃
• Refractive Index: 1.601
• PKA: -2.17±0.20(Predicted)
• CAS DataBase Reference: (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene) isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene) isocyanate(3779-63-3)
• EPA Substance Registry System: (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene) isocyanate(3779-63-3)

Safety Data

• Hazardous Substances Data: 3779-63-3(Hazardous Substances Data)

Usage

Uses

Hexamethylene Diisocyanate Isocyanurate Trimer is used as a building block for non-volatile polycondensation products, such as HDI-isocyanurate (HDI-IC) and HDI-biuret (HDI-BT).

Definition

ChEBI: A derivative of isocyanuric acid having a 6-isocyanatohexyl group at each of the 1-, 3- and 5-positions.

InChI:InChI=1/C27H33N9O9/c37-16-28-13-7-1-4-10-22(31-19-40)34-25(43)35(23(32-20-41)11-5-2-8-14-29-17-38)27(45)36(26(34)44)24(33-21-42)12-6-3-9-15-30-18-39/h22-24H,1-15H2

Synthetic route

cyanuric acid (108-80-5) + 1-chloro-6-isocyanato-hexane (13654-91-6) → (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 105 - 110℃; for 3h;

Hexamethylene diisocyanate (822-06-0) + butan-1-ol (71-36-3) → primary HDI n-butyl allophanate + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3)

Conditions	Yield
Stage #1: Hexamethylene diisocyanate With 1,1,1,3,3,3-hexamethyl-disilazane at 113 - 120℃; for 2.25h; Stage #2: butan-1-ol at 80℃; for 1h;

trioctylammonium caprolactamate + Hexamethylene diisocyanate (822-06-0) → hexamethylene diisocyanate uretdione + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3)

Conditions	Yield
With Bis(2-ethylhexyl)phosphoric acid In methanol at 80℃; for 7h; Reagent/catalyst; Cooling;

Hexamethylene diisocyanate (822-06-0) → (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3)

Conditions	Yield
With 2-Methylaziridine In ethyl acetate at 10℃; for 1h;

2-oxo-1,3-dioxolane-4-carboxylic acid (871835-30-2) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C27H40N6O9 (1621165-97-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;	100%

2-oxo-1,3-dioxolane-4-carboxylic acid (871835-30-2) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C30H44N6O12 (1621165-98-7)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 12h; Inert atmosphere;	100%

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol (678-39-7) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C54H51F51N6O9

Conditions	Yield
With dibutyltin dilaurate In 2-methyloctan-4-one; 4-methyl-2-pentanone at 75℃; for 4.5h;	97%

(2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + 1H,1H,2H,3H,3H-Perfluoro-1,2,-undecanediol (94159-84-9) → C57H57F51N6O12

Conditions	Yield
With dibutyltin dilaurate In 2-methyloctan-4-one; 4-methyl-2-pentanone at 75℃; for 1.5h;	91%

N,N'-bis(2,6-diisopropylphenyl)carbodiimide (2162-74-5) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C99H138N12O6

Conditions	Yield
at 110℃; for 7h; Sealed tube;	0.98%

C40H60N10O10 (180466-83-5) + C56H84N14O14 (180466-84-6) + 1H,1H,2H,2H-nonafluoro-1-hexanol (2043-47-2) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C42H51F27N6O9 + C64H80F36N10O14 + C86H109F45N14O19

Conditions	Yield
dibutyltin dilaurate In 4-methyl-2-pentanone at 72 - 76℃; for 5.5h;

C40H60N10O10 (180466-83-5) + C56H84N14O14 (180466-84-6) + N-methyl-1,1,2,2,3,3,4,4-nonafluoro-N-(2-hydroxyethyl)butane-1-sulphonamide (34454-97-2) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C45H60F27N9O15S3 + C68H92F36N14O22S4 + C91H124F45N19O29S5

Conditions	Yield
dibutyltin dilaurate In 4-methyl-2-pentanone at 72 - 75℃; for 2.5h;

2-(3,3,4,4,5,5,6,6,6-nonafluorohexylsulfonyl)ethanol (875628-34-5) + C40H60N10O10 (180466-83-5) + C56H84N14O14 (180466-84-6) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C48H63F27N6O15S3 + C72H96F36N10O22S4 + C96H129F45N14O29S5

Conditions	Yield
dibutyltin dilaurate In 4-methyl-2-pentanone at 72 - 75℃; for 2.5h;

3-(perfluorobutylsulfonyl)propan-1-ol (762241-70-3) + C40H60N10O10 (180466-83-5) + C56H84N14O14 (180466-84-6) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C45H57F27N6O15S3 + C68H88F36N10O22S4 + C91H119F45N14O29S5

Conditions	Yield
dibutyltin dilaurate In 4-methyl-2-pentanone at 72 - 75℃; for 2.5h;

Butane-1,4-diol (110-63-4) + 2-methoxy-ethanol (109-86-4) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) + pentaerythritol triacrylate (3524-68-3) → 1,4-butanediol; DESMODUR N-100; 2-methoxyethanol; methyl isocytocine; PETA; mixture of, heated

Conditions	Yield
Stage #1: Butane-1,4-diol; (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate; dibutyltin dilaurate In ISOPROPYLAMIDE at 40℃; for 0.5h; Stage #2: 2-amino-6-methylpyrimidin-4-ol In ISOPROPYLAMIDE at 40 - 87℃; Stage #3: 2-methoxy-ethanol; pentaerythritol triacrylate With hydroquinone more than 3 stages;

Butane-1,4-diol (110-63-4) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + 2-amino-6-methylpyrimidin-4-ol (3977-29-5) + pentaerythritol triacrylate (3524-68-3) → 1,4-butanediol; DESMODUR N-100; methyl isocytocine; PETA; mixture of, heated

Conditions	Yield
Stage #1: (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate; 2-amino-6-methylpyrimidin-4-ol In ISOPROPYLAMIDE at 87 - 90℃; Stage #2: pentaerythritol triacrylate With hydroquinone; dibutyltin dilaurate In ISOPROPYLAMIDE at 40 - 60℃; for 5.5h; Stage #3: Butane-1,4-diol In ISOPROPYLAMIDE at 50℃; for 5.5h;

oxiranyl-methanol (556-52-5) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C33H54N6O12 (125025-77-6)

Conditions	Yield
dibutyltin dilaurate at 35 - 55℃;

2-oxo-1,3-dioxolane-4-carboxylic acid (871835-30-2) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C33H48N6O15 (1445796-65-5)

Conditions	Yield
With dmap In tetrahydrofuran at 20℃;	130 g

(2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + 2-hydroxyethyl acrylate (818-61-1) → C39H60N6O15

Conditions	Yield
With dibutyltin dilaurate; 4-methoxy-phenol at 70 - 80℃; for 6h;

(2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + pentaerythritol triacrylate (3524-68-3) → C66H90N6O27

Conditions	Yield
With dibutyltin dilaurate; 4-methoxy-phenol at 70 - 80℃; for 5h;

1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine (131807-04-0) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C53H105N9O14Si2

Conditions	Yield
Stage #1: 1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine; (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate With dibutyltin dilaurate In tetrahydrofuran at 55℃; Stage #2: 3-(trimethoxysilyl)propan-1-amine In tetrahydrofuran for 0.0833333h;

1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine (131807-04-0) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C64H123N9O13Si

Conditions	Yield
Stage #1: 1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine; (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate With dibutyltin dilaurate In tetrahydrofuran at 55℃; Stage #2: 3-(trimethoxysilyl)propan-1-amine In tetrahydrofuran for 0.0833333h;

(2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) → C30H48N6O8

Conditions	Yield
With allyl alcohol In toluene

1-octyloxy-4-amino-2,2,6,6-tetramethylpiperidine (131807-05-1) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + pentaerythritol triacrylate (3524-68-3) → C69H108N8O21

Conditions	Yield
Stage #1: 1-octyloxy-4-amino-2,2,6,6-tetramethylpiperidine; (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate With dibutyltin(II) dilaurate In tetrahydrofuran at 55℃; for 0.166667h; Stage #2: pentaerythritol triacrylate In tetrahydrofuran

1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine (131807-04-0) + (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + pentaerythritol triacrylate (3524-68-3) → C72H124N8O17

Conditions	Yield
Stage #1: 1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine; (2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate With dibutyltin(II) dilaurate In tetrahydrofuran at 55℃; Stage #2: pentaerythritol triacrylate In tetrahydrofuran for 4.5h;

(2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + 4-Hydroxybenzophenone (1137-42-4) → C63H66N6O12

Conditions	Yield
With dibutyltin dilaurate at 60 - 105℃; for 10h;

(2,4,6-trioxotriazine-1,3,5(2H,4H,6H)-triyl)tris(hexamethylene)isocyanate (3779-63-3) + diisopropanolamine (110-97-4) → C42H81N9O12

Conditions	Yield
In water at 20 - 30℃;

Upstream product

• 822-06-0 Hexamethylene diisocyanate 
• 71-36-3 butan-1-ol 
• 108-80-5 cyanuric acid 
• 13654-91-6 1-chloro-6-isocyanato-hexane 

Relevant articles and documents

A novel compound, a method for preparing the same and a curing agent comprising the same

The present invention relates to a novel compound, a producing method thereof and a curing agent comprising the same. Disclosed are a compound comprising an amide bond and an aziridin group in a molecule by reacting a compound having one or more isocyanate groups with a compound comprising an aziridin group, and a curing agent comprising the same. According to the present invention, provided is a curing agent having a long pot life and a short aging time when being mixed with a main agent.(AA) Penetration rate %(BB) Wave numberCOPYRIGHT KIPO 2016

Method for preparing low viscosity tricondensate polyfunctional isocyanates

A method is described for preparing a tricondensate polyfunctional isocyanate composition, preferably having at least an isocyanurate and/or biuret group, which includes adding to a tricondensate polyfunctional isocyanate, or a mixture of different tricondensate polyfunctional isocyantes, obtained by (cyclo)condensation, in particular (cyclo)trimerization of one or several identical or different isocyanate monomers and optionally of another monomer, an allophanate of one or several identical or different isocyanates, or a mixture of different allophanates. The isocyanates or isocyanate monomer mixtures used for preparing the polyfunctional isocyanate(s) may be identical to or different from the isocyanate(s) or isocyanate mixture used for preparing the allophanate(s).