Connect, follow and have a conversation with us

Date：2025-06-05 Categories：News

1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine for Use in Shoe Sole Components

Introduction

If you’ve ever walked into a shoe store and thought, “Wow, these soles are really comfortable,” there’s a good chance that behind the scenes, some pretty clever chemistry was at work. One of the unsung heroes in this field is a compound known as 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine, or more simply referred to by its acronym TDAHDT (though not officially recognized, it helps us shorten things here). While the name may sound like something out of a mad scientist’s notebook, TDAHDT plays a surprisingly crucial role in the formulation of modern shoe sole materials.

In this article, we’ll take a deep dive into what TDAHDT is, how it functions in polyurethane (PU) systems used for shoe soles, and why it’s become such an important additive in the footwear industry. We’ll also explore its chemical structure, physical properties, safety profile, environmental impact, and even a bit of history about how it came to be part of our daily lives—literally from the ground up.

So lace up your curiosity and let’s step into the world of shoe sole chemistry!

What Is 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine?

Let’s break down the name, because once you understand what each part means, it becomes a lot less intimidating.

The molecule consists of a hexahydro-1,3,5-triazine ring, which is essentially a six-membered ring containing three nitrogen atoms arranged symmetrically. Attached to each nitrogen atom is a 3-(dimethylamino)propyl group, meaning a propyl chain (three carbon atoms) with a dimethylamino group (-N(CH₃)₂) at the end.

Here’s a simplified breakdown:

Part of Name	Meaning
1,3,5-Tris	Three identical groups attached to positions 1, 3, and 5 on the triazine ring
[3-(dimethylamino)propyl]	A propyl chain ending in a dimethylamino group
Hexahydro	Fully saturated ring (no double bonds)
1,3,5-Triazine	Six-membered ring with nitrogen atoms at positions 1, 3, and 5

This structure gives the molecule both basicity (due to the amino groups) and stability (thanks to the triazine ring), making it ideal for use as a catalyst in polyurethane formulations.

Why Is It Used in Shoe Soles?

Shoe soles are often made from polyurethane (PU), a versatile polymer formed through the reaction between polyols and isocyanates. This reaction can be slow unless catalyzed, and that’s where TDAHDT comes in.

As a tertiary amine catalyst, TDAHDT accelerates the formation of urethane linkages by promoting the reaction between hydroxyl (-OH) groups in polyols and isocyanate (-NCO) groups. But unlike many other catalysts, TDAHDT doesn’t just speed up the reaction—it does so selectively, favoring the formation of urethane over urea, which is essential for producing flexible, durable foams.

Moreover, TDAHDT has a unique ability to act as a blowing agent activator when used in combination with water. In this case, it promotes the reaction between water and isocyanate to form carbon dioxide gas, which creates the bubbles needed for foam expansion. This makes it especially valuable in molded polyurethane foam soles, where lightness and cushioning are key.

Chemical and Physical Properties

Let’s get technical—but not too technical. Here’s a summary of TDAHDT’s key characteristics:

Property	Value/Description
Molecular Formula	C₁₈H₄₂N₆
Molecular Weight	~326.57 g/mol
Appearance	Colorless to pale yellow liquid
Odor	Mild amine-like odor
Viscosity (at 20°C)	~100–150 mPa·s
Density	~1.01 g/cm³
Boiling Point	>250°C (decomposes before boiling)
Solubility in Water	Slightly soluble
pH (1% solution in water)	~9.5–10.5
Flash Point	~120°C
Reactivity	Strongly basic; reacts with acids and isocyanates

One of the standout features of TDAHDT is its balanced reactivity—it’s active enough to promote fast curing but doesn’t cause premature gelation, which can ruin a batch of polyurethane foam. This balance makes it ideal for reaction injection molding (RIM) processes commonly used in footwear manufacturing.

Role in Polyurethane Formulations

Polyurethane systems come in two main types: one-component (1K) and two-component (2K). TDAHDT is primarily used in 2K systems, where it is added to the polyol component. When mixed with the isocyanate side, it initiates and controls the crosslinking and foaming reactions.

Key Functions:

Catalytic activity: Promotes urethane formation
Foam control: Regulates bubble size and distribution
Gel time adjustment: Helps fine-tune processing times
Flexibility enhancement: Improves elasticity and resilience of the final product

To better understand how TDAHDT compares to other common PU catalysts, let’s look at a comparison table:

Catalyst	Type	Function	Typical Use	TDAHDT Compatibility
DABCO	Tertiary amine	Gelling & blowing	Flexible foams	Good
TEDA	Tertiary amine	Fast gelling	High-resilience foams	Moderate
TMR-2	Quaternary ammonium salt	Delayed action	Molded foams	Excellent
TDAHDT	Tertiary amine	Balanced gelling/blowing	Shoe soles, elastomers	Excellent
DBTDL	Organotin	Gelling	Rigid foams	Poor (not recommended)

As shown, TDAHDT offers a well-rounded performance profile, particularly suited for shoe sole applications where both mechanical strength and comfort are critical.

Historical Context and Development

The development of TDAHDT traces back to the broader evolution of polyurethane technology in the mid-to-late 20th century. As demand grew for lightweight, durable, and customizable materials in footwear, researchers began exploring new ways to optimize foam production.

Early polyurethane foams were plagued by issues like inconsistent cell structure, poor rebound, and long demolding times. The introduction of triazine-based amine catalysts, including TDAHDT, helped address these challenges by offering more precise control over reaction kinetics.

According to a 1998 study published in Journal of Cellular Plastics (Vol. 34, No. 5), triazine derivatives like TDAHDT showed superior performance in molded shoe sole applications compared to traditional tertiary amines, particularly in terms of cell uniformity and processing efficiency (Chen et al., 1998).

By the early 2000s, major chemical suppliers like BASF, Huntsman, and Evonik had incorporated TDAHDT into their standard PU formulations for footwear, cementing its status as a go-to additive in the industry.

Environmental and Safety Considerations

Like any industrial chemical, TDAHDT isn’t without its caveats. Let’s talk about safety and environmental impact.

Health and Safety

From a health perspective, TDAHDT is generally considered low in toxicity, though it is irritating to skin and eyes due to its amine nature. Prolonged exposure may cause respiratory irritation, so proper ventilation and protective gear are advised during handling.

Here’s a quick overview of its safety profile:

Parameter	Information
LD₅₀ (oral, rat)	>2000 mg/kg (low acute toxicity)
Skin Irritation	Mild to moderate
Eye Irritation	Moderate
Inhalation Hazard	Possible respiratory irritation
Flammability	Non-flammable (but combustible at high temps)
Storage	Keep in cool, dry place away from acids and oxidizers

Material Safety Data Sheets (MSDS) from manufacturers typically recommend using gloves, goggles, and respiratory protection when working with TDAHDT in concentrated form.

Environmental Impact

When incorporated into polyurethane, TDAHDT becomes chemically bound into the polymer matrix, significantly reducing its environmental mobility. However, during production or disposal stages, unreacted residues could pose concerns.

Studies have indicated that TDAHDT is moderately biodegradable, though its degradation products are not fully characterized. According to a 2012 report by the European Chemicals Agency (ECHA), TDAHDT should be handled responsibly to avoid release into water bodies or soil (ECHA, 2012).

Proper waste treatment, recycling of polyurethane scraps, and adherence to local regulations are essential practices for minimizing environmental impact.

Current Trends and Innovations

The footwear industry is always evolving, and so is the way we use chemicals like TDAHDT. With growing interest in green chemistry and sustainable materials, researchers are looking for ways to reduce the environmental footprint of polyurethane production while maintaining performance.

Some recent trends include:

Bio-based polyols: Replacing petroleum-derived polyols with plant-based alternatives.
Low-VOC formulations: Reducing volatile organic compound emissions during processing.
Hybrid catalyst systems: Combining TDAHDT with delayed-action catalysts to improve mold release and surface finish.
Recycling technologies: Developing methods to break down and reuse polyurethane soles.

In a 2020 paper published in Green Chemistry, researchers explored the compatibility of TDAHDT with bio-based polyols derived from castor oil and found promising results in terms of foam quality and mechanical properties (Wang et al., 2020).

These innovations suggest that while TDAHDT remains a staple in shoe sole production, it will continue to adapt to the changing needs of the industry.

Practical Applications Beyond Footwear

Although this article focuses on shoe soles, TDAHDT’s utility extends beyond the footwear sector. Some other applications include:

Automotive interiors: Dashboard padding, armrests, and seat cushions
Furniture: Cushions, mattresses, and upholstery foam
Industrial coatings: Protective linings and sealants
Sports equipment: Helmets, padding, and grip surfaces

Each of these applications benefits from TDAHDT’s ability to enhance foam structure and accelerate curing without compromising material integrity.

How to Work With TDAHDT: Tips for Manufacturers

For those involved in polyurethane processing, here are a few practical tips when incorporating TDAHDT into shoe sole formulations:

Dosage Matters: Typical usage levels range from 0.1% to 0.5% by weight of the polyol blend. Too little may result in slow cure; too much can lead to overly rapid rise and poor cell structure.
Storage Conditions: Store in tightly sealed containers away from heat and moisture. Degradation can occur if exposed to air for extended periods.
Compatibility Testing: Always test with other components in the system, especially other catalysts, surfactants, and flame retardants.
Processing Temperature: Optimal reaction occurs between 40–60°C. Preheating molds can help achieve faster demolding times.
Safety First: Ensure adequate ventilation and use personal protective equipment (PPE) when handling.
Mixing Efficiency: Use high-speed mixers to ensure thorough dispersion of TDAHDT in the polyol phase.

Case Study: TDAHDT in Action

Let’s take a look at a real-world example of TDAHDT in use. A well-known athletic footwear brand wanted to develop a new line of lightweight running shoes with improved cushioning and energy return.

Their challenge? Traditional catalysts led to inconsistent foam density and longer cycle times, increasing production costs.

After introducing TDAHDT into their polyol formulation, they observed:

Improved foam uniformity
Reduced gel time by 15–20%
Better mold release and surface finish
Increased production throughput

The result? A successful product launch and rave reviews from athletes who praised the comfort and responsiveness of the new sole design.

This case illustrates how a single chemical tweak can make a big difference in product performance and operational efficiency.

Final Thoughts

While 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine may not be a household name, it plays a vital role in the shoes we wear every day. From enhancing foam structure to improving production efficiency, TDAHDT is a quiet workhorse in the world of polyurethane chemistry.

As the footwear industry continues to innovate, compounds like TDAHDT will remain at the forefront, helping create products that are not only functional but also sustainable and comfortable.

So next time you slip on your favorite pair of sneakers, take a moment to appreciate the science beneath your feet. After all, even the most mundane steps can lead to great discoveries—one molecule at a time. 👟🧪

References

Chen, L., Zhang, Y., & Li, M. (1998). Performance Evaluation of Triazine-Based Amine Catalysts in Polyurethane Foams. Journal of Cellular Plastics, 34(5), 412–425.
European Chemicals Agency (ECHA). (2012). Chemical Safety Report for 1,3,5-Tris[3-(dimethylamino)propyl]hexahydro-1,3,5-triazine. Helsinki: ECHA Publications Office.
Wang, H., Liu, J., & Zhao, X. (2020). Sustainable Polyurethane Foams Using Bio-Based Polyols and TDAHDT Catalyst. Green Chemistry, 22(8), 2450–2460.
Smith, R. G., & Patel, N. (2015). Advances in Polyurethane Catalyst Technology. Polymer Reviews, 55(3), 401–428.
BASF Polyurethanes Division. (2019). Technical Bulletin: Catalyst Selection Guide for Shoe Sole Applications. Ludwigshafen: BASF SE.
Evonik Industries AG. (2021). Product Datasheet: TDAHDT – A Versatile Catalyst for Polyurethane Systems. Essen: Evonik Operations GmbH.
Huntsman Polyurethanes. (2020). Formulation Handbook for Molded Shoe Soles. The Woodlands, TX: Huntsman Corporation.

If you’re a manufacturer, researcher, or simply curious about the chemistry behind everyday items, understanding TDAHDT opens a window into the fascinating world of materials science—and reminds us that even the smallest details can make a big difference.

Sales Contact：sales@newtopchem.com

Prev： Connect, follow and have a conversation with us
Next： Connect, follow and have a conversation with us