A Complete Guide to Secondary Amine Catalysts

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Catalysts are an important additive in resin synthesis, and polyurethane is no exception. The catalysts commonly used in the synthesis of polyurethanes and their raw materials mainly fall into two categories: tertiary amine catalysts (including their quaternary ammonium salts) and organometallic compounds. Tertiary amine catalysts can be further classified into aliphatic amines, alicyclic amines, aromatic amines, and alcohol amines, as well as their ammonium salt compounds.

Triethylenediamine CAS 280-57-9

Pentamethyldiethylenetriamine CAS 3030-47-5

2,6,10-Trimethyl-2,6,10-triazaundecane CAS 3855-32-1

N,N,N',N'-Tetramethyl-1,6-hexanediamine CAS 111-18-2

2,4,6-Tris(dimethylaminomethyl)phenol 90-72-2

CAS 15875-13-5 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine

CAS 15875-13-5 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine

Hexadecyldimethylamine CAS 112-69-6

N,N-Dimethylethanolamine CAS 108-01-1

Triethylenediamine

Triethylenediamine, abbreviated as TEDA or DABCO, CAS 280-57-9, is a colorless or white crystalline solid at room temperature. It readily absorbs moisture from the air, causing deliquescence and caking. It is alkaline and turns yellow upon absorbing CO₂ from the air. It is highly soluble in acetone, benzene, and ethanol, and soluble in straight-chain hydrocarbon solvents such as pentane. At 25°C, 46 g can be dissolved in 1008 g of water. The relative density of the crystals (at 25°C) is approximately 1.14. The melting point of the pure compound is 158–159°C, the flash point is approximately 60°C, and the boiling point is 174°C. It sublimates readily and has a faint ammonia-like odor. Its vapor pressure is approximately 67 Pa at 21°C, 533 Pa at 50°C, and 7.7 kPa at 100°C. Pure TEDA is very low in toxicity; the LD₅₀ in mice is 2 g/kg. Inhalation of saturated TEDA vapor causes mild mucosal irritation and eye damage, while skin contact may cause allergic reactions.
Tris(2-ethylhexyl)diamine is solid at room temperature, making it inconvenient to use as a catalyst for polyurethane. In industrial applications, it is often melted and dissolved in low-molecular-weight diols to prepare an alcohol solution with a mass fraction of 33% (or other concentrations). Commonly used diols include dipropylene glycol, propylene glycol, diethylene glycol (diethylene glycol), and ethylene glycol.

Properties

Applications:

Tris(ethylenediamine) is a tertiary amine compound with a bicyclic structure and an ammonia-like odor. It serves as an organic synthesis intermediate and a raw material for synthesizing light-stabilizing agents. It is primarily used as a gelation catalyst for polyurethane foams and is widely applied in soft, semi-rigid, and rigid polyurethane foams, as well as elastomers. Additionally, it can be used as a curing catalyst for epoxy resins; a catalyst for ethylene polymerization, acrylonitrile polymerization, and ethylene oxide polymerization; an initiator in the production of pesticides such as hexahydropyridine; and an additive in hydrogen-free electroplating. Its derivatives can serve as corrosion inhibitors, emulsifiers, and other applications.

Pentamethyldiethylenetriamine

Pentamethyldiethylenetriamine is a highly reactive tertiary amine catalyst for polyurethane reactions. with CAS Number 3030-47-5. It is a colorless to pale yellow transparent liquid with a density of approximately 0.827 g/cm³. It is soluble in water and readily soluble in benzene, alcohols, and other solvents. It has low viscosity (approximately 2–3 mPa·s at 25°C), a boiling point of 198°C, and a flash point of 69°C. It is widely used in the production of rigid and flexible polyurethane foams. According to GHS classification, this substance is a flammable liquid and exhibits skin corrosivity and acute toxicity.

Properties

Applications

Pentamethyldiethylenetriamine is a highly active, strong-foaming polyurethane catalyst that is also used to balance the overall foaming and gelation reactions. It is widely used in various types of rigid polyurethane foam, including polyisocyanurate board foam. Due to its strong foaming effect, it improves foam flowability, thereby enhancing the production process and improving product quality.
In addition to rigid foam formulations, pentamethyldiethylenetriamine can also be used in the production of polyether-based polyurethane flexible block foam and molded foam.

2,6,10-Trimethyl-2,6,10-triazaundecane

2,6,10-Trimethyl-2,6,10-triazaundecane is a chemical intermediate. At room temperature, it is a colorless to yellow transparent liquid with a CAS of 3855-32-1, a density of 0.9 ± 0.1 g/cm³, a boiling point of 239.2 ± 8.0 °C, and a flash point of 80.9 ± 9.0 °C. This substance is a flammable liquid and is corrosive to the skin; it must be transported as a Class C hazardous material.

Applications

2,6,10-Trimethyl-2,6,10-triazaundecane is primarily used as a low-odor foaming/gel-balancing catalyst in polyether-based polyurethane flexible and rigid foams, as well as in coatings and adhesives. It is particularly suitable for cold-molded HR foam to improve cell openness and is compatible with the Maxfoam foaming process. It is synthesized through a three-step process involving the Michael addition of methylamine to acrylonitrile, followed by catalytic hydrogenation and methylation, with a total yield of 83.7%.

N,N,N',N'-Tetramethyl-1,6-hexanediamine

N,N,N',N'-Tetramethyl-1,6-hexanediamine, abbreviated as TMHDA, is an organic compound with the chemical formula C₁₀H₂₄N₂ and CAS Number 111-18-2. It has a boiling point of 209.54°C and appears as a colorless to pale yellow transparent liquid that is soluble in water.

Properties:

Applications

N,N,N',N'-Tetramethyl-1,6-hexanediamine is a heat-insensitive catalyst suitable for use in various polyurethane foams, particularly rigid polyurethane foam. It acts as a foaming/gel balance catalyst, improving surface curing and adhesion.

2,4,6-Tris(dimethylaminomethyl)phenol

2,4,6-tris(dimethylaminomethyl)phenol, commonly referred to as DMP-30, is a catalyst for the isocyanate trimerization reaction (CAS 90-72-2). It is a pale yellow to pale red, transparent, viscous liquid that is soluble in water.

Properties

Applications

2,4,6-tris(dimethylaminomethyl)phenol is a catalyst for isocyanate trimerization reactions. It exhibits higher catalytic selectivity for polyisocyanurate (PIR) reactions than for polyurethane (PUR) reactions and is therefore commonly used in formulations for polyisocyanurate reactions. This product is a relatively weak catalyst that requires a higher dosage in formulations. It promotes a mild reaction with a steady rate increase and good flow properties. The resulting products exhibit the high-temperature resistance and flame-retardant properties characteristic of PIR. It can be used to formulate prepregs. It is also used as a curing agent for thermosetting epoxy resins and as an acid neutralizer.

1,3,5-tris(3-dimethylaminopropyl) hexahydro-s-triazine (s-triazine)

1,3,5-Tris(3-dimethylaminopropyl)hexahydro-s-triazine (s-triazine) is a colorless to pale yellow transparent liquid with a very faint odor or is nearly odorless; it is highly soluble in water. CAS 15875-13-5.

Properties

Applications

1,3,5-tris(3-dimethylaminopropyl)hexahydro-s-triazine (s-triazine) is a highly active tri-catalyst for polyurethane rigid foam with excellent foaming and gelling capabilities, typically used in combination with other catalysts. It is primarily used to catalyze polyurethane (PU) and polyisocyanurate (PIR) reactions. In practice, its catalytic selectivity for PU is slightly higher than for PIR reactions. It is commonly used in laminated panels, spray-applied rigid foam, and molded rigid foam and is particularly suitable for PIR rigid foam panels and various foaming processes (including all-water foaming), demonstrating excellent performance in water-foamed rigid foam systems. It is also suitable for microcellular polyurethane elastomers and high-resilience foam products.

N-hexadecyl-N,N-dimethylamine

N-hexadecyl-N,N-dimethylamine is a colorless to yellow liquid (CAS No. 112-69-6) with a relative density of 0.79 at 25°C and a viscosity of 9 mPa·s at 25°C. Its boiling point is >197°C, flash point is 65°C, and vapor pressure is 2.34 kPa. It is insoluble in water.

Applications

N-hexadecyl-N,N-dimethylamine promotes the cross-linking of polyester-based PU soft-pack foam and improves the surface curing of full-skin foam (semi-rigid foam).