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Poly ε caprolactone diol

Manufactured by Merck Group
Sourced in Germany

Poly(ε-caprolactone) diol is a synthetic polymer widely used in various laboratory applications. It is a linear, aliphatic polyester with a molecular weight range that can be adjusted for specific needs. The core function of this material is to serve as a versatile building block or precursor in the synthesis and formulation of diverse polymeric systems.

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7 protocols using poly ε caprolactone diol

1

Synthesis of Polycaprolactone-based Polyurethanes

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Poly(ε-caprolactone) diol (PCLD, Mn = 2000 g/mol), dimethyl-sulfoxide (99.9 %, DMSO, stored on molecular sieve), 1,6-hexamethylene diisocyanate (HDI, reagent grade), Tin(II) 2-ethylhexanoate (reagent grade) were purchased from Sigma-Aldrich (Darmstadt, Germany) and were used as received. D(+)-sucrose (puriss, Ph. Eur. 6.) from Reanal (Budapest, Hungary) was powdered and dried in a vacuum oven at 40 °C for overnight before use. Toluene (analytical grade), acetone (99.9%, HPLC grade) from Sigma-Aldrich (Darmstadt, Germany), methanol (HPLC grade) from Merck (Darmstadt, Germany) and hexane (HPLC grade) from VWR (Debrecen, Hungary) were used without any purification.
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2

Microfluidic Seeding and Polyurethane Nanoparticles

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For seeding of microfluidic devices: polydimethylsiloxane (PDMS) (Sylgard 184 silicone elastomer kit) was purchased from Dow Corning. Fibrinogen (cat. no. F8630), fibronectin (cat. no. C010), poly-L-lysine (cat. no P4707) and thrombin (cat. no. T9549) were purchased from Sigma-Aldrich.
For PU synthesis: Poly(ε-caprolactone)-diol (PCL-diol (2,000 g mol−1), Poly(ethylenglicole) (PEG 2000 g mol−1), n-BOC Serinol, Dibutyl Dilaurate (DBTL), and 1,6 Hexamethylene diisocyanate (HDI) were purchased from Sigma-Aldrich (Milan, Italy).
For PU NP preparation: L-α-phosphatidylglycerol (Egg-PG), 1,2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[carboxyl(polyethylene glycol)-2000] (DSPE-PEG-COOH) and L-α-phosphatidylethanolamine-N-(lissamine-rhodamine B-sulfonyl) (Egg-Liss-Rhod PE) were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Holo-Tf Human (cat. no. T4132), N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC), N-Hydroxysuccinimide (NHS), 2-(N-morpholino)ethanesulfonic acid (MES) hemisodium salt, were purchased from Sigma-Aldrich (Milan, Italy).
Red fluorescent carboxylate PS NPs (cat. no. F8801, F8810, FluoSpheres) were purchased from Life Technologies and Spherotech (cat no. CFP-0562-2).
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3

Synthesis of Photocurable PCL-based Hydrogels

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Poly(ε-caprolactone) diol (PCL90-diol; Mn ~10 k g/mol), trimethylamine (Et3N), acryloyl chloride, 4-dimethylaminopyridine (DMAP), 2,2-dimethoxy-2-phenylacetophenone (DMP), 1-vinyl-2-pyrrolidinone (NVP), potassium carbonate (K2CO3), sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium chloride (NaCl), octamethylcyclotetrasiloxane (D4), triflic acid, hexamethyldisilazane (HMDS), ε-caprolactone, stannous 2-ethylhexanoate, sodium chloride (NaCl), sodium bicarbonate (NaCO3), potassium chloride (KCl), dipotassium hydrogen phosphate trihydrate (K2HPO4·3H2O), magnesium chloride hexahydrate (MgCl2·6H2O), calcium chloride (CaCl2), sodium sulfate (Na2SO4), phosphate buffered saline (PBS; pH 7.4), and tris(hydroxymethyl)aminomethane were obtained from Sigma-Aldrich. Anhydrous magnesium sulfate (MgSO4) was obtained from Thermo Fisher Scientific. Tetramethyldisiloxane (tetra-SiH), tetrakis(dimethylsiloxy)siloxane (tetrakis-SiH), and platinum-divinyl-tetramethyldisiloxane complex in xylene (Karstedt’s catalyst) were obtained from Gelest. Reagent-grade dichloromethane (CH2Cl2) and NMR-grade CDCl3 were dried over 4 Å molecular sieves prior to use.
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4

Polyurethane Synthesis with Crosslinked Porous Scaffold

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For the polyurethane synthesis poly(ε-caprolactone)diol (PCD, Mn = 2000 g/mol), polyethylene glycol (PEG, Mn = 600 g/mol), 1,6-hexamethylene diisocyanate (HDI, reagent grade, 98%), tin(II) 2-ethylhexanoate (Sn(Oct)2), Mn = 405.12 g/mol, 92.5–100%), and 1,4-butanediol (BDO) Reagent Plus® (99%) M = 90.12 g/mol were purchased from Sigma-Aldrich (Darmstadt, Germany) and D,L-lactic acid (LA, 88% assay, from Spektrum 3D Ltd. Debrecen, Hungary) was used. D(+)-sucrose (puriss, Ph. Eur. 6.) from Reanal (Budapest, Hungary) was powdered and dried in a vacuum oven at 40 °C overnight before use as a crosslinker. Toluene (analytical grade) and dimethyl-sulfoxide (99.9%, DMSO, stored in a molecular sieve) from Sigma-Aldrich (Darmstadt, Germany) were used as solvents without any purification. Sodium chloride (a.r.) from Molar Chemicals Ltd. (Halásztelek, Hungary) was used to form the scaffold. Reverse osmosis filtered water (RO) was used for the dissolution of salt. The RO was produced with an HFRO1.0 device manufactured by Hidrofilt Ltd. (Nagykanizsa, Hungary).
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5

Synthesis and Characterization of PEG-based Polyurethane

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Poly(ethylene glycol) of 2050 Da, poly(propylene glycol) of 2000 Da, poly(ε-caprolactone)-diol of 2000 Da, hexamethylene diisocyanate (HMDI) 99%, dibutyltin dilaurate 95% were purchased from Sigma Aldrich and used as received without further purification. Anhydrous toluene and anhydrous diethyl ether are sourced from TEDIA. Toluene was further dried and stored over pre-activated 4 Å molecular sieves.
Gel permeation chromatography (GPC) was conducted on a Viscotek TDAmax which consists of three components – the GPCmax integrated solvent and sample delivery module, the TDA 302 Triple Detector Array, and the OmniSEC software. The TDA 302 array incorporates refractive index (RI) and light scattering detectors as well as a viscometer. 2 columns (2 × PLgel 10 μm mixed-B (500 to 10 000 000)) were applied in sequence for separation. THF was used as the eluent at 1.0 ml min−1 with column and detector temperature at 40 °C. Polystyrene standard (Mw 21 960, dn/dc = 0.185, IV = 0.1471, PDI = 1.02) was used for the multi-detector calibration to calibrate the detector constants. Samples' concentration was input to determine their dn/dc and Mw. 1H nuclear magnetic resonance (NMR) spectra were recorded using a JEOL 500 MHz NMR spectrometer (Tokyo, Japan) at room temperature.
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6

Synthesis and Characterization of Biodegradable Polyurethane

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Isophorone diisocyanate (IPDI, product number 4098719), 2,2-bis(hydroxymethyl)propionic acid (DMPA, product number 106615), 1,4-butanediol (product number 493732), poly(ε-caprolactone) diol (PCL diol; Mn = 2000 Da, product number 189421), triethylamine (TEA, product number 471283), methyl ethylketone (MEK), ethylenediamine (product number 03550), PEO (Mn = 900 kDa, product number 189456), MTT (product number M5655), and acetone were purchased from Sigma-Aldrich Chemical Corporation (St Louis, MO, USA). All chemicals were used as received. Antibiotics, trypsin–ethylenediaminetetraacetic acid, Dulbecco’s modified Eagle’s medium (DMEM), and fetal bovine serum (FBS) were purchased from HyClone.
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7

Polymer Synthesis and Characterization

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D,L-lactide (Lot no.: 2009002968) and glycolide (Lot no.: 1210002433) were purchased from Corbion (Gorinchem, The Netherlands). Tin (II) 2-ethylhexanoate (92.5–100%, Lot no.: 1003287404), poly(ε-caprolactone) diol (PCL, Mn = 2000 g.mol−1, WXBD4206V), 1,3-propanediol (>98%, Lot no.: S768868143) were provided by Sigma Aldrich (St-Quentin Fallavier, France) and used as received. 1,4-Dioxane (ACS-Reagent, Lot no.: M1600), distilled in the presence of CaH2, was provided by Honeywell (Offenbach, Germany). Diethyl ether (Batch Number: V1G060031H), n-pentane (Batch Number: V9C059249D), dichloromethane (Batch Number: V1M602021N) and sodium chloride (Batch Number: V1L077212C) were provided by Carlo Erba Reagents (Val de Reuil, France). Hexamethylene diisocyanate (HDI; >98%, Lot no.: IVRTI-NJ) was provided by TCI Europe (Zwikndrecht, Belgium) and used as received.
Zinc diethyldithiocarbamate (ZDEC, Lot no.: A-223K) and high-density polyethylene film (HDPU, Lot no.: C-221) were provided by Hatano Research Institute, Food and Drug Safety Center (Hadano, Japan).
Dulbecco’s Modified Eagle Medium (DMEM/F-12, Lot no.: RNBL4062), PenicillinStreptomycin (Lot No.: 0000205667) and GlutaMAXTM (Lot no.: 2554717) were purchased from ThermoFisher Scientific (Waltham, MA, USA). Tissue Culture Polystyrene (TCPS) 96-well plates were purchased from Becton Dickinson (Le Pont-de-Claix, France).
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