Trimethylolpropane tris(2-methyl-1-aziridinepropionate)

• CAS: 64265-57-2
• Catalog Number: ACM64265572
• Category: Main Products
• Molecular Weight: 467.6
• Molecular Formula: C₂₄H₄₁N₃O₆
• Synonyms: Trimethylolpropane tris(2-methyl-1-aziridinepropionate)
• IUPAC Name: [2-[3-(2-methylaziridin-1-yl)propanoyloxy]-2-[3-(2-methylaziridin-1-yl)propanoyloxymethyl]butyl]3-(2-methylaziridin-1-yl)propanoate
• SMILES: CCC(COC(=O)CCN1CC1C)(COC(=O)CCN2CC2C)OC(=O)CCN3CC3C
• InChI Key: OEOQTSUNXODXQL-UHFFFAOYSA-N
• Flash Point: >110ºC
• Density: 1.1
• Exact Mass: 453.28400
• Hazard Statements: Xn:Harmful

Case Study

Trimethylolpropane Tris(2-Methyl-1-Aziridinepropionate) as a Crosslinking Agent for the Preparation of UV-Curable Waterborne Polyurethane Acrylate Emulsion

Wang, Rui, et al. Coatings, 2022, 12(9), 1293.

Researchers developed a dual-cured UV and aziridine waterborne polyurethane acrylate emulsion using trimethylolpropane tris(2-methyl-1-aziridinepropionate) (Sac-100) which serves as a trifunctional aziridine crosslinking agent to link carboxylic groups. The impact of varying Sac-100 concentrations on gel fraction, tensile properties, hardness, wear resistance, water resistance, and surface morphology of the cured films and coatings was examined.
Key Findings
· As the Sac-100 content increased, the gel fraction, tensile strength, elongation at break, and toughness of the films initially rose, then fell, while wear weight loss and water absorption ratios consistently decreased. Moreover, Sac-100 influenced the surface roughness of the coatings. A comprehensive assessment indicated that the optimal Sac-100 concentration is 4 wt% within the UV/AZ-WPUA system.
· At this optimal level, the coating film exhibits a gel fraction of 89.78 wt%, a tensile strength of 34.58 MPa, an elongation at break of 343.64%, toughness of 65.08 MJ/m3, a wear loss of 4.7 mg, and a water absorption ratio of 11.63 wt%.
· The dual-cured films demonstrate significant enhancements over the UV-cured film without Sac-100, with a 155.4% increase in tensile strength, 129.3% increase in toughness and a 25.7% increase in hardness while reducing water absorption ratio by 27.1%.

Trimethylolpropane Tris(2-Methyl-1-Aziridinepropionate) Used for the Preparation of Star-Shaped and Long-Chain Branched Polylactic Acid

Gu, Liangliang, et al. Journal of Rheology, 2017, 61(4), 785-796.

A trifunctional aziridine linker, trimethylolpropane tris(2-methyl-1-aziridinepropionate) (TTMAP), was melt blended with linear poly(lactic acid) (PLA) to create (i) star-shaped PLA and (ii) long chain branched (LCB) PLA, employing pyromellitic dianhydride (PMDA) alongside TTMAP.
Synthesis Strategy
The melt blending of linear PLA with TTMAP yielded a three-arm star-shaped PLA that demonstrated higher viscosity, lacking strain hardening during extensional flow. The formation of long chain branched PLA occurred through sequential reactions using PMDA followed by TTMAP with PLA.
Key Findings
· PMDA converted some hydroxyl end groups in PLA chains to carboxyl groups; however, this reaction was less vigorous and not fully realized compared to the reaction with TTMAP.
· The star-shaped PLA showed increased viscosity while lacking any strain hardening during extensional flow but the LCB PLA demonstrated significant extensional hardening. The dependency of the extensional hardening coefficient on strain rate suggested a low concentration of LCB molecules in the LCB PLA, potentially forming an H-shaped topological structure.
· This branching method, unlike traditional approaches (such as free radical chemistry or epoxy-functional oligomers), resulted in strain hardening with a minimal increase in shear viscosity.

Custom Q&A

What is the molecular formula of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The molecular formula is C23H39N3O6.

What are the synonyms for Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

Some synonyms include 64265-57-2 and 2-(((3-(2-Methylaziridin-1-yl)propanoyl)oxy)methyl)butane-1,2-diyl bis(3-(2-methylaziridin-1-yl)propanoate).

What is the molecular weight of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The molecular weight is 453.6 g/mol.

When was Trimethylolpropane tris(2-methyl-1-aziridinepropionate) created and modified?

It was created on August 19, 2012, and last modified on October 21, 2023.

What is the IUPAC name of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The IUPAC name is [2-[3-(2-methylaziridin-1-yl)propanoyloxy]-2-[3-(2-methylaziridin-1-yl)propanoyloxymethyl]butyl] 3-(2-methylaziridin-1-yl)propanoate.

What is the InChI of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The InChI is InChI=1S/C23H39N3O6/c1-5-23(32-22(29)8-11-26-14-19(26)4,15-30-20(27)6-9-24-12-17(24)2)16-31-21(28)7-10-25-13-18(25)3/h17-19H,5-16H2,1-4H3.

What is the InChIKey of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The InChIKey is OEOQTSUNXODXQL-UHFFFAOYSA-N.

What is the canonical SMILES of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The canonical SMILES is CCC(COC(=O)CCN1CC1C)(COC(=O)CCN2CC2C)OC(=O)CCN3CC3C.

What is the CAS number of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

The CAS number is 64265-57-2.

What is the physical description of Trimethylolpropane tris(2-methyl-1-aziridinepropionate)?

It is a liquid.