PGS elastomers originating from three prepolymers were prepared first and then the structure and properties were studied. The PGS prepolymer synthesis was adapted from established methods[7 ] by a polycondensation reaction of glycerol and sebacic acid with different molar ratios as 1:1, 2:3, and 3:2 mixtures of anhydrous glycerol (Merck) and sebacic acid (Merck). Briefly, they were mixed in an airtight glass jar that was partially immersed in a heated silicone bath. The mixture was gradually heated to 120°C under nitrogen gas flow and stirred with a rotor at 50 rpm for 24 h. The reaction was initially carried out at atmospheric pressure, with a low flow of nitrogen across the reaction mixture. The gas flow was then stopped and vacuum (at −20 kPa) was applied for 24 h. Polycondensation results in a highly viscous uncrosslinked pre polymer. PGS films were obtained by curing the pre polymer in a Petri dish in a vacuum oven (at −20 kPa) at set cure times and 135°C.
Sebacic acid
Manufactured by Merck Group
Sourced in United States, Germany
Sebacic acid is a dicarboxylic acid with the chemical formula CH3(CH2)8COOH. It is a naturally occurring compound and is used as a chemical intermediate in various industrial applications.
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Lab products found in correlation
Glycerol, by Merck Group (26 mentions)
Fetal bovine serum (fbs), by Thermo Fisher Scientific (11 mentions)
Penicillin streptomycin, by Thermo Fisher Scientific (8 mentions)
Ethanol, by Merck Group (5 mentions)
Succinic acid, by Merck Group (5 mentions)
Dimethyl sulfoxide (dmso), by Merck Group (5 mentions)
Citric acid, by Merck Group (4 mentions)
Polyethylene glycol, by Merck Group (3 mentions)
Glycerol, by Thermo Fisher Scientific (3 mentions)
Azelaic acid, by Merck Group (3 mentions)
Phosphate buffered saline (pbs), by Thermo Fisher Scientific (3 mentions)
Glutaraldehyde, by Merck Group (3 mentions)
Taurine, by Merck Group (2 mentions)
Palmitic acid, by Merck Group (2 mentions)
Oleic acid, by Merck Group (2 mentions)
Linoleic acid, by Merck Group (2 mentions)
Diethyl sebacate, by Merck Group (2 mentions)
Novozym 435, by Merck Group (2 mentions)
15 pentadecalactone, by Merck Group (2 mentions)
Hplc grade chloroform, by Merck Group (2 mentions)
54 protocols using sebacic acid
1
Synthesis and Characterization of PGS Elastomers
2
Synthetic Polymeric Biomaterials Fabrication
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Sebacic acid (99.0%), malonic acid (99.0%), glutaric acid (99.0%), polycaprolactone triol (PCL triol, 300 Da), glycerol (99.0%), PEG (200, 1000, 2000 Da), N,N′-diisopropylcarbodiimide (DIC, 99.0%), 4-dimethylaminopyridine (DMAP, 99.0%), anhydrous N,N-dimethylformamide (DMF, 99.8%), anhydrous dimethyl sulfoxide (DMSO, 99.9%), anhydrous dichloromethane (DCM, 99.8%), deuterochloroform (99.96 atom% D), sodium octyl sulfate (SOS, 95.0%), dexamethasone (98.0%), fluorescein isothiocyanate isomer I (FITC, 90.0%), fluorescein sodium salt, hexamethylene diisocyanate (HMDI, 99.0%), dibutyltin dilaurate (Sn(II), 95.0%), and PBS (pH 7.4) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Cyanine5.5 carboxylic acid (Cy5.5, 95.0%) was purchased from Lumiprobe Corporation (Hallandale Beach, FL, USA). Tetrodotoxin (TTX) was obtained from Abcam (Cambridge, MA, USA). TTX ELISA kits were purchased from Reagen LLC (Moorestown, NJ, USA). Dulbecco’s minimum essential medium (DMEM), fetal bovine serum (FBS), and Penicillin Streptomycin was purchased from Thermo Fisher Scientific (Waltham, MA, USA).
3
Synthesis of Polycaprolactone and PGS Polymers
4
Biomimetic Bone Scaffold Fabrication
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Glycerol, sebacic acid, Gelatin, Ɛ-caprolactone (PCL), and hydroxyapatite nanoparticles (particle size < 100 nm) were purchased from Sigma-Aldrich (USA). Chloroform and Isopropanol were ordered from Dr. Mojallali Chemical Industries Complex (Iran). Hexamethylene diisocyanate (HDI) was purchased from Merck (Germany). Phosphate buffer saline (pH 7.3) was obtained from the GIBCO. Adipose-derived mesenchymal stem cells were supplied from the Stem Cell Technology Research Center (Tehran, Iran) and used for cellular experiments.
5
Lipid Standard Procurement and Characterization
6
Lipid and Metabolite Profiling Reagents
7
Enzyme-Catalyzed Synthesis of Polyesters
8
Synthesis of Rosin Acid-based Polyester
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Example 1
This example describes the general synthesis of rosin acid-based polyester (Sample 1).
A 2-L buchi reactor was charged with 356.8 Foral AX (Rosin Acid, available from Pinova), 166 g of neopentyl glycol diglycidyl ether (available from Sigma-Aldrich), and 0.57 g of tetraethyl ammonium bromide (available from Sigma-Aldrich). The mixture was heated to 175° C. over a three hour period with stirring under nitrogen, and then maintained at 175° C. for five more hours and until the acid value of the resulting rosin-diol (Scheme I supra) was 1.8 mg of KOH/g of resin. To the mixture was then added 306 g propylene glycol (available from Archer-Daniels Midland), 844.5 grams of sebacic acid (available from Sigma-Aldrich) and 2 g of TC400 catalyst (available from Elf-Atochem). The mixture was slowly heated to 195° C. over a six hour period, followed by vacuum distillation until the resin viscosity of 15 and acid value of 13.5 mg of KOH/g of resin was obtained. The resin was then discharged and allowed to cool to room temperature.
9
Synthesis of Polyester Compounds
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Ethylene glycol (E), Succinic acid (S), Citric acid(C), Sebacic acid (Se), and Propan-1,3-diol (P) were utilized as such after being bought from Sigma Aldrich. The catalyst, titanium tetraisopropoxide (TiTPo), was bought from Lancaster. The same grade of all other chemicals and solvents was utilized.
10
Fabrication and Evaluation of Gelatin-Based Biomaterials
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The materials used in this study were sourced from various suppliers. Gelatin (Gel) (CAS: 9000-70-8), sebacic acid (CAS: 111-20-6), glycerol (CAS: 56-81-5), dimethyl sulfoxide (DMSO), and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were purchased from Sigma Aldrich/USA. N-Hydroxysuccinimide (NHS), 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), acetic acid, and glutaraldehyde (25% aqueous solution) were obtained from Merck/Germany. Phosphate-buffered saline (PBS), Dulbecco’s modified Eagle’s medium (DMEM), GlutaMAX (high glucose), and penicillin/streptomycin were provided by GIBCO/USA. Trypsin-EDTA (0.05% trypsin in 0.04 mM EDTA) was purchased from Bioidea. The human dermal fibroblast (HDF) cell line was acquired from the Cell Bank of the Pasteur Institute.
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