Three different types of PEGdA macromers with varying susceptibility to hydrolytic degradation were synthesized by a two-step process as previously reported [35 (link)]. Briefly, PEG (4000 MW, Fluka, Buchs, Switzerland) was reacted with either chloroacetyl chloride, 2-chloropropionyl chloride, or 4-chlorobutuyrl chloride (Sigma-Aldrich, St. Louis, MO) in the presence of triethylamine (TEA, Sigma) at a 1:4:1.8 molar ratio in dry dichloromethane (Sigma). After 24 hours reaction at room temperature, the reactants were filtered, washed with sodium bicarbonate and water, dried with anhydrous sodium sulfate, and then precipitated in ethyl ether. After recovery, each resulting intermediate product was reacted with sodium acrylate (5X molar ratio) in dry dimethylformamide (Acros, Morris Plains, NJ) for 30 hours at 50, 85, and 100 °C to yield PEG-bis-(acryloyloxy acetate) [PEG-bis-AA], PEG-bis-(acryloyloxy propanoate) [PEG-bis-AP], and PEG-bis-(acryloyloxy butyrate) [PEG-bis-AB], respectively. The products were purified by filtration, rotary evaporation, and precipitation in ethyl ether and dried under vacuum. The structures of each PEGdA and the degree of acrylation were determined from the 1H-NMR (Brucker 300 MHz, CDCl3) spectra. All samples achieved acrylation efficiencies greater than 90%.
2 chloropropionyl chloride
Manufactured by Merck Group
2-chloropropionyl chloride is a chemical compound that is commonly used as an intermediate in organic synthesis. It is a colorless liquid with a pungent odor. The compound is primarily used in the production of various pharmaceutical and agrochemical products.
Automatically generated - may contain errors
Lab products found in correlation
Triethylamine tea, by Merck Group (2 mentions)
Chloroacetyl chloride, by Merck Group (1 mentions)
Dry dichloromethane, by Merck Group (1 mentions)
Dry dimethylformamide, by Thermo Fisher Scientific (1 mentions)
Trifluoroacetic acid, by Thermo Fisher Scientific (1 mentions)
Sodium citrate tribasic dihydrate, by Shanghai Chemical Reagent (1 mentions)
Copper chloride, by Merck Group (1 mentions)
Formaldehyde solution, by Thermo Fisher Scientific (1 mentions)
Acetic acid, by Thermo Fisher Scientific (1 mentions)
Sodium bicarbonate, by Thermo Fisher Scientific (1 mentions)
N isopropylacrylamide nipam, by Merck Group (1 mentions)
Tris 2 aminoethyl amine, by Merck Group (1 mentions)
Polycaprolactone diol pcl diol, by Merck Group (1 mentions)
Chloroform, by Merck Group (1 mentions)
Sodium borohydride, by Merck Group (1 mentions)
Acetonitrile, by Merck Group (1 mentions)
Dimethylformamide, by Merck Group (1 mentions)
Diethyl ether, by Merck Group (1 mentions)
3 protocols using 2 chloropropionyl chloride
1
Synthesis of Hydrolytically Tunable PEGdA Macromers
2
Synthesis and Characterization of PZLLys
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Poly(ε-benzyloxycarbonyl-l -lysine) (PZLLys) were prepared according to the method previously described (Mn = 7000, and Mw/Mn = 1.16) [35 (link)]. N-Isopropylacrylamide (NIPAM, 97%, Kohjin Co., Kumamoto, Japan) was purified by recrystallization from a benzene/n-hexane mixture (65/35 v/v). 2-Chloropropionyl chloride (98%) was purchased from Sigma-Aldrich (Shanghai, China) and used as received. N,N′-Dimethylformamide (DMF) was dried and distilled from anhydrous magnesium sulfate under reduced pressure. Hydrobromic acid in glacial acetic acid (HBr/AcOH, 45% w/v) and trifluoroacetic acid (TFA) was purchased from Alfa Aesar (Shanghai, China) and used without further purification. Sodium citrate tribasic dihydrate and hydrogen tetrachloroaurate trihydrate were obtained from Shanghai Chemical Reagent Company (Shanghai, China). The ligand tris[2-(dimethylamino)ethyl]amine (Me6TREN) was synthesized as reported in the literature [53 (link)]. All the other reagents were of analytical grade and used as received.
3
Synthesis and Characterization of Stimuli-Responsive Polymer Materials
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Acetonitrile (EMD), chloroform (Sigma), diethyl ether (Sigma), dimethylformamide (DMF; Sigma, anhydrous), dichloromethane (DCM; EMD, HPLC grade), formaldehyde solution (Fisher), tetrahydrofuran (THF; EMD, anhydrous), acetic acid (Fisher, glacial), hydrochloric acid (HCl; EMD, 12.1 M), sodium hydroxide (NaOH, EMD), N-isopropyl acrylamide (NIPAM; Sigma), poly(caprolactone diol) (PCL diol; Sigma, Mn ~530), triethylamine (TEA; Sigma, 99.5%), copper chloride (CuCl; Sigma, ≥99%), sodium bicarbonate (NaHCO 3 ; Fisher), magnesium sulfate (MgSO 4 ; J.T. Baker, anhydrous), 2-chloropropionyl chloride (Sigma), tris(2-aminoethyl) amine (TREN, Sigma, 96%), sodium borohydride (Sigma), and aluminum oxide (Fluka) were used as received.
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