Description
N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine (also known as Quadrol) is a monomer based on ethylenediamine used in the production of polyurethane coatings, adhesives, cosmetics and personal care products. It acts as a chelating agent due to the presence of four hydroxyl groups and as a cross-linking agent due to its two amino groups. It is widely used as a component of polymers and copolymers, especially those designed for UV crosslinked polyurethane polymers, dendritic aminopolymers, conductive polymers, inks and coatings. In addition, Quadrol is also used to produce resins, as well as in the manufacture of surfactants, plasticisers and other chemical products.
Chemical Properties
A clear colorless to pale yellow viscous liquid. N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine(Tetrahydroxypropyl ethylenediamine) is a chelating agent that binds with metal ions or metallic compounds, preventing them from adhering to a surface (such as skin, hair, or clothing) or causing contamination, such as in the case of trace amounts of iron.
Uses
N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine is used as a solvent and preservative. A component of the bacteria-killing substance in sugarcane, it is very alkaline and may be irritating to the skin and mucous membranes. It might also cause skin sensitization.
Uses
N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine can be used as cross-linking agent and catalyst in the manufacture of urethan foams; in epoxy resin curing; as complexing agent, humectant, emulsifier, plasticizer.
Definition
ChEBI: Tetrakis(2-hydroxypropyl)ethylenediamine is an amino alcohol.
Application
N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine can be used as:
(1) A monomer in the synthesis of covalently cross-linked and amorphous shape memory polyurethane (SMPU) foams that are used in biomedical applications, which includes SMPU actuators for treating ischemic stroke, thrombus removal activated by laser light, self-deployable SMP neuronal electrodes, vascular stents, sutures in microsurgery, ocular implants, bandages, cell manipulation, and cell therapy.
(2) A precursor in the preparation of self-healing CFRPs (carbon fiber reinforced polymer) which are thermally responsive with excellent mechanical properties.
(3) A crosslinking agent to create a hydrogel that is biocompatible and supports the growth of neural cells. Hydrogels are specifically designed to mimic the properties of the extracellular matrix (ECM), in promoting cell proliferation. The purpose of the hydrogel in this context is to act as an extracellular matrix (ECM) substitute, providing a supportive environment for cell growth and guiding cell adhesion and outgrowth.
brand name
Neutrol TE (BASF);
Quadrol (BASF).
Flammability and Explosibility
Non flammable
Synthesis
N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine can be prepared by the ring-opening addition reaction of ethylenediamine and propylene oxide under the action of a catalyst.
in vitro
Results show that viability of macrophages incubated with Quadrol (N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine) at concentrations of 0.5 mM, 1 mM and 4mM are identical to that for controls. Viability, however, is reduced to 50% of control at concentrations of 16 mM to 32 mM. After four hours, at concentrations of 1 mM and 4 mM, Quadrol produces enhanced spreading of 88% and 80%, respectively, as compared to the control of 28%. Quadrol, at a concentration of 16 mM, shows reduced percentage of spreading of macrophages after four hours. Exposure of macrophages to 1.0 mM or 4.0 mM Quadrol concentrations enhances phagocytic activity, 41% and 57%, respectively, over that of the cells exposed to media alone (34%).
in vivo
On day eight after the implantation, the amount of collagen in the implants of normal mice injected with Quadrol (N,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine) exceeds controls by more than 200% (p<0.025). By day 11, the collagen content increases to over 300% higher than controls (p<0.01) and by the end of two weeks after wounding, the time interval typically required for normal and complete wound healing, the collagen accumulated in the implants of the Quadrol-treated mice is about 50% above control (p<0.1). The accumulation of collagen in the implants of Quadrol treated STZ-diabetic mice about 100% above the untreated diabetic control on days 8 to 11. By day 14, the collagen deposition has increased to 200% above the controls (p<0.0 5).
