O,O'-Bis(2-aminopropyl)polypropyleneglycol
[CAS# 9046-10-0]

Identification

• Classification: Catalysts and additives >> Polymer
• Name: O,O'-Bis(2-aminopropyl)polypropyleneglycol
• Synonyms: Polypropylene glycol bis(2-aminopropyl ether)
• Molecular Formula: (C₃H₆O)_nC6H16N2O
• Molecular Weight: ~230
• CAS Registry Number: 9046-10-0
• EC Number: 695-873-3
• SMILES: CC(N)CO.CC(O)CO

Properties

• Density: 0.948 g/mL (25 ºC)
• Index of Refraction: 1.447

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Hazard Statements: H302-H304-H312-H314-H318-H335-H411-H412
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P331-P362+P364-P363-P391-P403+P233-P405-

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - single exposure	STOT SE	3	H335
Aspiration hazard	Asp. Tox.	1	H304
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Skin corrosion	Skin Corr.	1	H314

• Transport Information: UN 2735

Discovory and Applicatios

O,O'-Bis(2-aminopropyl)polypropyleneglycol, commonly referred to as bis(2-aminopropyl) polypropyleneglycol (BAPG), is a chemical compound notable for its multifunctional properties and versatility in various industrial applications. This compound is synthesized from polypropyleneglycol (PPG) through a reaction with 2-aminopropyl groups, resulting in a product with enhanced reactivity and utility in different chemical processes. BAPG is recognized for its ability to act as a surfactant, stabilizer, and multifunctional additive, making it valuable in industries ranging from coatings to personal care products.

The discovery of BAPG can be traced back to the broader research into polyols and their derivatives during the mid-20th century. Polypropyleneglycol, developed for its unique properties as a polymeric alcohol, laid the foundation for the synthesis of various functionalized derivatives, including BAPG. The introduction of amino groups to polypropyleneglycol was a significant advancement, providing new chemical functionalities that expanded the scope of applications for polyol-based products. This compound has since gained attention in both academic research and industrial applications due to its favorable properties.

One of the primary applications of O,O'-Bis(2-aminopropyl)polypropyleneglycol is in the formulation of surfactants and emulsifiers. In the cosmetic and personal care industry, BAPG is utilized for its ability to stabilize emulsions, enhance the texture of creams and lotions, and improve the overall feel of products on the skin. Its surfactant properties enable the efficient solubilization of oil and water phases, making it a popular choice in formulations for shampoos, conditioners, and skin care products. The compound’s mildness and biocompatibility also make it suitable for use in sensitive formulations, where skin irritation is a concern.

In the coatings industry, BAPG serves as a reactive diluent and viscosity modifier. Its incorporation into paint and coating formulations enhances the application properties of the products, such as flow and leveling, while also improving adhesion and durability. BAPG can be used in various types of coatings, including waterborne, solventborne, and UV-cured systems, contributing to the performance and aesthetic qualities of the final product. The compound's ability to improve the wetting properties of surfaces is particularly beneficial in applications where adhesion to substrates is critical.

Another significant application of O,O'-Bis(2-aminopropyl)polypropyleneglycol is in the field of adhesives and sealants. Due to its amine functionality, BAPG can react with isocyanates to form polyurethane products, which are known for their strong bonding capabilities and flexibility. This reaction allows for the development of high-performance adhesives suitable for a wide range of substrates, including metals, plastics, and composites. BAPG-modified adhesives exhibit excellent mechanical properties, making them ideal for structural applications in industries such as automotive and construction.

BAPG is also explored for its potential in the field of biomaterials. The presence of amino groups in its structure allows for further functionalization, enabling the development of bioactive materials for medical and pharmaceutical applications. Research has indicated that BAPG-based polymers can be designed for drug delivery systems, tissue engineering scaffolds, and other biomedical applications due to their favorable biocompatibility and tunable properties.

In addition to these applications, O,O'-Bis(2-aminopropyl)polypropyleneglycol is being studied for its role in catalysis and as a precursor for the synthesis of various polymeric materials. The ability to tailor its molecular structure and properties opens avenues for innovative applications in advanced materials science.

In summary, the discovery and application of O,O'-Bis(2-aminopropyl)polypropyleneglycol have significantly impacted multiple industries, particularly cosmetics, coatings, adhesives, and biomaterials. Its multifunctional properties, stemming from its unique chemical structure, make it a valuable component in a variety of formulations and applications. As research continues to explore its full potential, BAPG is poised to play an even more prominent role in the development of advanced materials and innovative solutions across diverse sectors.

References

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DOI: 10.1007/s00044-021-02700-1

2015. An efficient one-pot synthesis of polyfunctionalized 2H-pyrroline derivatives by reaction of β-enaminocarbonyls, arylglyoxals and amines. Journal of the Iranian Chemical Society, 12(9).
DOI: 10.1007/s13738-015-0739-0

2012. Low-generation dendrimers with a calixarene core and based on a chiral C2-symmetric pyrrolidine as iminosugar mimics. Beilstein Journal of Organic Chemistry, 8.
DOI: 10.3762/bjoc.8.107