O,O'-Bis(2-aminopropyl)polypropyleneglycol

• CAS: 9046-10-0
• Catalog Number: ACM9046100-9
• Category: Main Products
• Molecular Weight: 103.12g/mol
• Molecular Formula: C4H9NO2
• Synonyms: Poly(propylene glycol) bis(2-aminopropyl ether)
• IUPAC Name: (3S,4S)-pyrrolidine-3,4-diol
• Canonical SMILES: C1C(C(CN1)O)O
• InChI: InChI=1S/C4H9NO2/c6-3-1-5-2-4(3)7/h3-7H,1-2H2/t3-,4-/m0/s1
• InChI Key: JCZPOYAMKJFOLA-IMJSIDKUSA-N
• Appearance: Liquid
• Application: The purpose of O,O'-Bis(2-aminopropyl)polypropyleneglycol is to provide good alkali and water resistance, as well as moderate acid resistance. When used to cure epoxy resins, it enhances electrical properties. Polyetheramines, like this product, offer unique properties that make them valuable in a wide range of epoxy applications including coatings, potting materials, construction materials, composites, and adhesives.
• Complexity: 58.7
• Covalently-Bonded Unit Count: 1
• EC Number: 618-561-0
• Exact Mass: 103.063329g/mol
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Heavy Atom Count: 7
• Monoisotopic Mass: 103.063329g/mol
• Rotatable Bond Count: 0
• XLogP3: -1.7

Case Study

O,O'-Bis(2-aminopropyl)polypropyleneglycol hydrogel for controlled fertilizer release

Sabadini, Rodrigo Cesar, et al. Journal of Applied Polymer Science 135.2 (2018): 45636.

A new super absorbent gel was synthesized based on gellan gum and O,O'-Bis(2-aminopropyl)polypropyleneglycol using EDC/NHS as crosslinkers, aiming to develop its controlled release in fertilizers. Infrared spectroscopy and thermal analysis confirmed the crosslinking. Morphological analysis showed that samples with higher crosslinking points had a denser structure. The swelling degree of high acyl gellan gum hydrogel was equivalent to 145 times its dry weight, while it was 77 times when low acyl gellan gum was used. The hydrogel also showed water retention of 450 minutes compared to 280 minutes for pure water, which demonstrated good moisture control and was suitable for use in arid climates. They also demonstrated a maximum release of about 400 mg per gram for commercial fertilizers KH PO and about 300 mg per gram for NPK 20-5-20.
Hydrogels were prepared by dissolving 0.1 g of gellan gum (HA or LA) in 20 ml of ethanesulfonic acid buffer (pH 5 ± 5). After complete dissolution, 0.4 mL of O,O'-Bis(2-aminopropyl)polypropyleneglycol was added to the solution. Different crosslinking densities were obtained by adding 1, 2, 3, and 4 mmol of N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) to the solution, and the samples were named 1, 2, 3, and 4 according to the amount of EDC/NHS added in the samples. After mixing for 2 h, the hydrogels were frozen in a refrigerator at 220 ± 8 °C for about 6 h and then warmed to room temperature. This process was repeated three times. The samples were washed several times and dried at 40 ± 8 °C; no further treatment was used.

O,O'-Bis(2-aminopropyl)polypropyleneglycol for functional transparent quasi-solid-state dye-sensitized solar cells

Sygkridou, Dimitra, Andreas Rapsomanikis, and Elias Stathatos. Solar Energy Materials and Solar Cells 159 (2017): 600-607.

Five different organic-inorganic hybrid materials were synthesized using different molecular weights (230, 400 and 2000) of O,O-bis(2-aminopropyl)polypropylene glycol, O,O-bis(2-aminopropyl)polyethylene glycol (900) or O,O-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol (600) and 3-isocyanatopropyltriethoxysilane, which were used as gelling agents and ion conductors for quasi-solid-state electrolytes in dye-sensitized solar cells (DSSCs). Initially, the electrolyte was liquid, allowing the electrolyte molecules to penetrate the semiconductor nanoparticles, and as the acetic acid solvent decomposition occurred, they gelled, bonding the two electrodes together. The stability of the different electrolytes was thermally characterized, and their conductivity was also measured. Functional quasi-solid-state DSSCs were achieved using transparent TiO2 thin films deposited on conductive glass using a spin coating method. The structural properties of the photoanode were studied by scanning electron microscopy and porosity analysis. The experimental results showed that the thickness of the prepared transparent film was between 3.5 and 4.2 μm. The dye-sensitized solar cells (DSSCs) made of transparent TiO2 thin films were electrically studied to determine if there was any variation in their performance when using different quasi-solid electrolytes. The results showed that all the cells had comparable results and the overall performance of converting sunlight to electrical energy was 3.3-3.9% depending on the mixed materials in the quasi-solid electrolyte.
Five different organic-inorganic hybrid materials were prepared and used in five different electrolytes to facilitate their gelation process. The organic-inorganic hybrid materials were prepared according to the following procedure. O,O-bis(2-aminopropyl)polypropylene glycol of various molecular weights (M 230, 400 and 2000), or O,O-bis(2-aminopropyl)polyethylene glycol (M 900) or O,O-bis(2-aminopropyl)polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol and 3-isocyanatopropyltriethoxysilane (ICS; molar ratio ICS/diamine = 2) were placed in a container for reaction (acylation reaction) to produce urea linkage groups between polymer units and inorganic parts. Organic-inorganic hybrid materials are abbreviated according to the precursor materials used to make them and their molecular weights (PPG230-ICS, PPG400-ICS, PPG2000-ICS, PEG900-ICS and ED600-ICS).

Preparation of novel ion-conducting organic electrolytes from O,O'-Bis(2-aminopropyl)polypropyleneglycol

Dahmouche, Karim, et al. Journal of sol-gel science and technology 13 (1998): 909-913.

Two groups of hybrid organic-inorganic composites with ion-conducting properties have been prepared by sol-gel process. The first group was prepared from a mixture of lithium salts and 3-isocyanatopropyltriethoxysilane (IsoTrEOS), O,O-bis(2-aminopropyl)polypropyleneglycol. These materials produce chemical bonds between the organic phase (polymer) and the inorganic phase (silica). The second group was prepared from a mixture of tetraethoxysilane (TEOS), polypropyleneglycol and lithium salts by ultrasonic method. There is no chemical bonding between the organic and inorganic phases in these samples. The lithium ion conductivity σ of all these materials has been studied by electrochemical impedance spectroscopy up to 100°C. A systematic study of the effect of lithium concentration, polymer chain length and polymer to silica weight ratio on σ shows that σ has a strong dependence on the preparation conditions. The dynamic properties of lithium ions and polymer chains as a function of temperature between -100°C and 120°C were studied using lithium solid-state NMR measurements. The ionic conductivity of the two families was compared, with a particular focus on the nature of the bonds between the organic and inorganic components.
For the first type of material, equimolar amounts of 3-isocyanatopropyltriethoxysilane (IsoTrEOS) and O,O-bis(2-aminopropyl)polypropylene glycol were stirred together in tetrahydrofuran (THF) under reflux for 6 h. THF was evaporated and the pure hybrid precursor (OEt)3Si-PPG-Si(OEt)3 was obtained. 0.5 g of this precursor was mixed with 1 ml of ethanol containing NH4F (NH4F/Si=0.005), to which the required amount of lithium salt (LiClO4) was added. Finally, 0.2 ml of water was added under stirring, and an overall wet gel was obtained within 4 h. The ethanol was then slowly removed to obtain a rubbery material body.

O,O'-Bis(2-aminopropyl)polypropyleneglycol for bio-based non-isocyanate synthesis

Fu, Yuqi, et al. Industrial & Engineering Chemistry Research 58.47 (2019): 21513-21520.

A green synthesis route for bio-based non-isocyanate thermoplastic polyoxamide-urea (POXAU) containing flexible poly(propylene oxide) segments was proposed. Hexamethylenediamine-diester (HDODE) was synthesized by the reaction of 1,6-hexamethylenediamine with excess diethyl oxalate. Four H2N-terminated polyoxamide prepolymers (PrePOXA) were synthesized by melt polycondensation of HDODE with O,O'-bis(2-aminopropyl)polypropylene glycol. PrePOXA was chain-extended with bis(hydroxyethyl)hexamethylenediurethane as a chain extender to prepare four chain-extended POXA or POXAU. POXAU was characterized by size exclusion chromatography, FT-IR, 1H-NMR, WAXS, differential scanning calorimetry, thermogravimetric analysis, and tensile testing. POXAU has an Mn of up to 29900 g mol-1, a melting temperature of 148 to 156 °C, an initial decomposition temperature of more than 242 °C, a tensile strength of up to 60 MPa, and an elongation at break of 8% to 16%. Crystalline bio-based thermoplastic polyoxadioxamide-urea with excellent thermal and mechanical properties was successfully synthesized via a non-isocyanate route.
3.16 g (0.0100 mol) of hexanedioxamide-dieste (HDODE) and 2.88 g (0.0128 mol) of O,O'-bis(2-aminopropyl)polypropylene glycol were placed in a 100 mL three-necked round-bottom flask equipped with a distillation adapter, a condenser, and a receiver. The mixture was stirred at 170 °C under reduced pressure at 30 °C for 0.5 h. Thereafter, the pressure in the flask was always maintained at 3 mmHg. This was continued for a period of time until no ethanol was distilled out. Finally, the PrePOXA-1 and D230:HDODE molar ratio (x) was 1.28 and the degree of polymerization to obtain the repeat unit (DP) or m was 3.6.