As a thermo-responsive elastomer, the membrane polymer (6-arm 96% PCL-co-04% PGMA) was synthesized by ring-opening polymerization of ε-caprolactone (CL; Sigma-Aldrich, MO, USA) and glycidyl methacrylate (GMA; Sigma-Aldrich). Briefly, dipentaerythritol (0.5 mmol, Sigma-Aldrich), hydroquinone (2.1 mmol, Sigma-Aldrich), and distilled CL (329 mmol) were prepared in a 3-necked flask. The mixture was stirred at 110 °C for 10 min. GMA (21 mmol) was added, and the reaction was allowed to proceed for 10 min. Then, a solution of 1,5,7-triazabicyclo [4.4.0] dec-5-ene (Sigma-Aldrich) and anhydrous acetonitrile (Sigma-Aldrich) (3.5 mmol) was added and reacted at 110 °C for 6 h under a nitrogen atmosphere. The product was dissolved in chloroform and precipitated using cold diethyl ether (Sigma-Aldrich). The final product, 6-arm 96% PCL-co-04% PGMA (%: molar ratio), was obtained after vacuum drying for 24 h.
ε caprolactone cl
Manufactured by Merck Group
Sourced in United States, Germany
ε-caprolactone (CL) is a cyclic ester compound used as a precursor in the synthesis of various polymers. It serves as a building block for the production of polycaprolactone and other polyester materials. The core function of ε-caprolactone is to provide a versatile monomer for polymer synthesis applications.
Automatically generated - may contain errors
Lab products found in correlation
Stannous octoate, by Merck Group (3 mentions)
Dichloromethane, by Merck Group (3 mentions)
Diethyl ether, by Merck Group (2 mentions)
Stannous octoate sn oct 2, by Merck Group (2 mentions)
Sn oct 2, by Merck Group (2 mentions)
Chloroform, by Merck Group (2 mentions)
Dipentaerythritol, by Merck Group (1 mentions)
Triazabicyclo 4.4.0 dec 5 ene, by Merck Group (1 mentions)
Hydroquinone, by Merck Group (1 mentions)
Glycidyl methacrylate, by Merck Group (1 mentions)
Anhydrous acetonitrile, by Merck Group (1 mentions)
Peg1000, by Merck Group (1 mentions)
Peg 1500, by Merck Group (1 mentions)
L lactide la, by Boehringer Ingelheim (1 mentions)
Dexamethasone (dex), by Tokyo Chemical Industry (1 mentions)
Ir783, by Merck Group (1 mentions)
3 4 5 dimethylthiazol 2 yl 2 5 diphenyltetrazolium bromide mtt, by Merck Group (1 mentions)
2 bromoisobutyryl bromide, by Merck Group (1 mentions)
Copper 1 bromide, by Merck Group (1 mentions)
Dimethyl phenylphosphonite, by Thermo Fisher Scientific (1 mentions)
14 protocols using ε caprolactone cl
1
Synthesis of Thermoresponsive 6-Arm PCL-co-PGMA
2
Synthesis of Functionalized Polyesters
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2,2-bis(bromomethyl)-1,3-propanediol, sodium iodide and sodium bisulfite were the products of Aladdin Biochemical Technology Co., Ltd. (Shanghai, China). Ethyl chloroformate was acquired from Wuhan Changcheng Chemical Technology Development Co., Ltd. (Wuhan, China). PEG1000 (number-average MW Mn = 1000 Da), PEG1500 (Mn = 1500 Da), Zn(HMDS)2, stannous octoate and ε-caprolactone (CL) were bought from Sigma-Aldrich. Glycolide (GA) and d ,l -lactide (LA) were acquired from Hangzhou Medzone Biotech Ltd. (Hangzhou, China). Iohexol was the product of TCI Development Co., Ltd. (Shanghai, China). Tetrahydrofuran (THF) and TEA were stirred in the presence of calcium hydride (CaH2) for 24 h and then collected by distillation. CCK-8 for mammalian cells was bought from Beyotime Co., Ltd. (Shanghai, China). The other chemical reagents provided by Sinopharm Chemical Reagent Co. (Shanghai, China) were utilized without additional treatment.
3
Lignin-Based Polymer Composite Synthesis
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ABS (HI121H) was purchased
from LG. Chem.
Co. Ltd., Korea. It was of general-purpose injection molding grade
with a melt flow index of 23 g/10 min at 220 °C/10 kg load, as
per ASTM D1238. Soft kraft lignin (the content of lignin and ash was
about 97.1 and 1.6 wt %) was supplied by the Domtar Corporation (North
Carolina, U.S.A). According to the manufacturer, it was brown fine
powder (elemental composition (wt % dry basis): carbon = 62.8, hydrogen
= 5.0, oxygen = 28.1, sulfur = 3.6) with a bulk density of 348 kg/m3, number-average molecular weight (Mn) of 913 g/mol, weight-average molecular weight (Mw) of 1323 g/mol, and polydispersity of 1.45. ε-Caprolactone
(CL), dibutyltin dilaurate (DBTDL), acetic acid, and tetrahydrofuran
(THF) were obtained from Sigma-Aldrich. Two thermal antioxidants,
SONGNOX 1010 (phenolic-based, Songwon) and SONGNOX 1680 (phosphite-based,
Songwon) were used for composite preparation. All reagents were used
without further purification.
from LG. Chem.
Co. Ltd., Korea. It was of general-purpose injection molding grade
with a melt flow index of 23 g/10 min at 220 °C/10 kg load, as
per ASTM D1238. Soft kraft lignin (the content of lignin and ash was
about 97.1 and 1.6 wt %) was supplied by the Domtar Corporation (North
Carolina, U.S.A). According to the manufacturer, it was brown fine
powder (elemental composition (wt % dry basis): carbon = 62.8, hydrogen
= 5.0, oxygen = 28.1, sulfur = 3.6) with a bulk density of 348 kg/m3, number-average molecular weight (Mn) of 913 g/mol, weight-average molecular weight (Mw) of 1323 g/mol, and polydispersity of 1.45. ε-Caprolactone
(CL), dibutyltin dilaurate (DBTDL), acetic acid, and tetrahydrofuran
(THF) were obtained from Sigma-Aldrich. Two thermal antioxidants,
SONGNOX 1010 (phenolic-based, Songwon) and SONGNOX 1680 (phosphite-based,
Songwon) were used for composite preparation. All reagents were used
without further purification.
4
Synthesis of MPEG-based Copolymers
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Methoxy poly(ethylene glycol) (MPEG) (Sigma-Aldrich, number-average molecular weight (Mn = 750)), and Sn(Oct)2 (Sigma-Aldrich, Yongin, Korea) were used as received. l -lactide (LA; Boehringer Ingelheim, Blanquefort, France) was recrystallized in ethyl acetate twice. ε-Caprolactone (CL; Sigma-Aldrich) was distilled over CaH2 under reduced pressure. Dex and Dex(p) were purchased from Tokyo Chemical Industry Co., Ltd. (TCI; Fukaya City, Japan). Hexafluoro-2-propanol (HFIP), IR-780, and IR-783 were purchased from Sigma-Aldrich.
5
Synthesis and Characterization of Functional Polymers
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ε-caprolactone (CL; Sigma-Aldrich, New Jersey, USA) was dried by calcium hydride (CaH2; ChengDu KeLong Chemical Co., Ltd., China) and distilled under reduced pressure. Triethylamine (TEA) (ChengDu KeLong Chemical Co., Ltd.) was dried over CaH2 and distilled. 2-Bromoisobutyryl bromide (98%), stannous octoate (Sn(Oct)2; 95%), copper (I) bromide (CuBr; 99%), pentaerythritol, 2,2′-disulfanediyldiethanol, 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT), 2,2′-bipyridine (BPy), DL-dithiothreitol (DTT) were purchased from Sigma-Aldrich Co. (St Louis, MO, USA) and used as received. 2-Methacryloyloxyethyl phosphorylcholine (MPC) was supplied by Nanjing Joy-Nature Ltd (Nanjing, China) and used as received. Doxorubicin (DOX)·HCl was neutralized with TEA to remove the hydrochloride to make it become hydrophobic DOX. Toluene and tetrahydrofuran (THF) (ChengDu KeLong Chemical Co., Ltd) were dried by refluxing over sodium and distilled before used. All the other reagents and solvents used were analytically pure and without further purification.
6
Synthesis of PEG-Polycaprolactone Polymers
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Poly(ethylene
glycol) (PEG, MW = 20 000, Sigma) and ε-caprolactone
(CL, Sigma) were dried in a vacuum oven at 60 °C to remove residual
water before use. Stannous octoate (Sn(Oct)2, Sigma), triethylamine
(TEA, Sigma), acryloyl chloride (Sigma), dichloromethane (Sigma),
dimethyl phenylphosphonite (Acros Organics), 2,4,6-trimethylbenzoyl
chloride (Sigma), lithium bromide (Sigma), and 2-butanone (Sigma)
were used as received.
glycol) (PEG, MW = 20 000, Sigma) and ε-caprolactone
(CL, Sigma) were dried in a vacuum oven at 60 °C to remove residual
water before use. Stannous octoate (Sn(Oct)2, Sigma), triethylamine
(TEA, Sigma), acryloyl chloride (Sigma), dichloromethane (Sigma),
dimethyl phenylphosphonite (Acros Organics), 2,4,6-trimethylbenzoyl
chloride (Sigma), lithium bromide (Sigma), and 2-butanone (Sigma)
were used as received.
7
Synthesis of PEG-Caprolactone Polymers
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All chemicals and solvents were of reagent grade and used without additional purification unless otherwise stated. Dichloromethane was acquired from Sigma-Aldrich (St. Louis, MI, USA) and dried using phosphorus pentoxide. Toluene was dried by distillation with sodium and was obtained from Fischer Chemical (Waltham, MA, USA). Poly(ethylene glycol) methyl ether (MePEG, Mn = 5000), ε-caprolactone (CL), and a 2 M solution of hydrogen chloride in diethyl ether were acquired from Sigma-Aldrich (St. Louis, MI, USA). CL was dried with calcium hydride and distilled prior to use. Me-PEG (Mn = 5000) was dried twice by azeotropic distillation in toluene that was distilled off completely. Dimethylformamide (DMF) and acetonitrile (ACN) were acquired from Fisher Chemical (Waltham, MA, USA) and Honeywell (Charlotte, NC, USA), respectively.
Primaquine diphosphate 98% was obtained from Sigma-Aldrich (St. Louis, MI, USA). The gold complexes AuSe and AuS were synthesized and characterized as previously described [14 (link)].
Primaquine diphosphate 98% was obtained from Sigma-Aldrich (St. Louis, MI, USA). The gold complexes AuSe and AuS were synthesized and characterized as previously described [14 (link)].
8
Synthesis of PCL and PCL-PLLA Copolymers
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ε-Caprolactone (CL) was purchased from Sigma-Aldrich
(Co., Steinheim, Germany). For PCL polymer synthesis, we used the
ROP method and stannous octoate (Sn(Oct)2) (Sigma-Aldrich
Chemical Co) was added as a catalyst. In the beginning, 10 g of CL
was heated up to 130 °C, consequently, 0.1 g (1 wt %) of Sn(Oct)2 was added for starting polymerization and this continued
under stirring conditions with N2 gas for 6 h (seeFigure 8 a). Next, the polymer
dissolved in chloroform (Merck Chemical Co) or dichloromethane (Merck
Chemical Co), and then the mixture precipitated in an excess of diethyl
ether in a cold bath.
Like PCL polymer, the ROP method was employed using lactic
acid
and CL monomers.dl -lactide monomers were purchased from
Sigma-Aldrich (Co., Steinheim, Germany). For PCL–PLLA co-polymer
synthesis, lactic acid and CL monomers with a ratio of 2.5 to 97.5
were added to a 50 mL round-bottom flask. After increasing the temperature
to 140 °C under stirring in a nitrogen atmosphere, 0.1 g (1 wt
%) of Sn(Oct)2 was added for catalyzing the reaction. After
6 h, the obtained co-polymer was dissolved in chloroform or dichloromethane,
and then to remove excess catalyst and the unreacted monomers, the
mixture precipitated in an excess of diethyl ether in a cold bath
and left at room temperature for solvent evaporation.
(Co., Steinheim, Germany). For PCL polymer synthesis, we used the
ROP method and stannous octoate (Sn(Oct)2) (Sigma-Aldrich
Chemical Co) was added as a catalyst. In the beginning, 10 g of CL
was heated up to 130 °C, consequently, 0.1 g (1 wt %) of Sn(Oct)2 was added for starting polymerization and this continued
under stirring conditions with N2 gas for 6 h (see
dissolved in chloroform (Merck Chemical Co) or dichloromethane (Merck
Chemical Co), and then the mixture precipitated in an excess of diethyl
ether in a cold bath.
Like PCL polymer, the ROP method was employed using lactic
acid
and CL monomers.
Sigma-Aldrich (Co., Steinheim, Germany). For PCL–PLLA co-polymer
synthesis, lactic acid and CL monomers with a ratio of 2.5 to 97.5
were added to a 50 mL round-bottom flask. After increasing the temperature
to 140 °C under stirring in a nitrogen atmosphere, 0.1 g (1 wt
%) of Sn(Oct)2 was added for catalyzing the reaction. After
6 h, the obtained co-polymer was dissolved in chloroform or dichloromethane,
and then to remove excess catalyst and the unreacted monomers, the
mixture precipitated in an excess of diethyl ether in a cold bath
and left at room temperature for solvent evaporation.
9
Enzymatic Synthesis of Polycaprolactone
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ε-Caprolactone (CL) was purchased from Sigma Aldrich (St. Louis, MO, USA) and distilled over CaH2 under reduced pressure before each use. Methionine (Met) and cysteine (Cys) amino acids as well as Novozym®435 (N435, Novozymes, Bagsværd, Denmark), the acrylic resin-immobilized form of Candida antarctica lipase B (CALB), were purchased from Sigma Aldrich (St. Louis, MO, USA) and used after freeze drying. Anhydrous toluene was freshly distilled over sodium under nitrogen atmosphere prior each use. Hexanol was freshly distilled on molecular sieve under vacuum prior use. Other chemicals (N-Boc cysteine, N-Boc methionine, 4 Å molecular sieve, p-toluenesulfonic acid, and NaHCO3) and solvents (methanol, diethyl ether, ethanol, chloroform, and dichloromethane) were purchased from Sigma Aldrich (St. Louis, MO, USA) and used without further purification or drying.
10
Synthesis and Characterization of PEGylated Nanocarriers
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Poly(ethylene glycol) (PEG) with Mn 1.5 kDa (PEG1.5k, Sigma-Aldrich, Milan, Italy), monomethoxy-poly(ethylene glycol) with Mn 2.0 kDa (mPEG L , Sigma-Aldrich, Italy) and monomethoxy-poly(ethylene glycol) with Mn 1.0 kDa (mPEG S , Nanocs Inc., USA) were dehydrated by azeotropic distillation with dry toluene in a Dean-Stark trap. ε-Caprolactone (CL, Sigma-Aldrich, Italy) was distilled over CaH 2 under vacuum. Stannous-(2-ethylhexanoate)2 (Sn(oct) 2 ), N-hydroxysuccinimide (NHS), N,N′-dicyclohexylcarbodiimide (DCC), triethylamine (TEA), dimethylaminopyridine (DMAP), tosyl chloride (TsCl), folic acid (Fol), propargylamine, triphenylphosphine (PPh 3 ), silver(I) oxide, potassium iodide and sodium azide were used without further purification. Copper wires (Carlo Erba, Italy) were treated with H 2 S0 4 for 3 min, washed with water and methanol, and finally dried under vacuum in an oven for 30 minutes at 60°C. 1,4-butandiol, 1-hexanol, N,N-dimethylformamide (DMF) and dichloromethane (DCM) were dried before use according to standard procedures. All the other solvents (analytical grade) were purchased from Sigma-Aldrich and used as received. (2-Hydroxypropyl)β-cyclodextrin (HPβCD, DS 0.9), Nile Red (NR) and Human Serum Albumin (HSA) were from Sigma (Italy).
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