Separation of Complex Branched Polymer Architectures. Albena Lederer
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1 Separation of Complex Branched Polymer Architectures Albena Lederer
2 2-dimensional separation A 2 +B 3 Poly(urea-urethane)s n, hb Fraction 9 n, lin hb-pu-ph lin-pu (ppm ) ,35 Fraction 17 0,30 0,25 aromatic dendritic 0,20 p-urethane m i 0,15 o-urethane p-urea o-urea 0,10 0, (p p m ) , Fractions
3 2-dimensional separation A 2 +B 3 Poly(urea-urethane)s hb-pu-ph n, hb lin-pu n, lin sample SEC with PVPcalibration* SEC- MALLS** M w M w /M n M w fraction fraction fraction fraction m i 0,35 0,30 0,25 0,20 0,15 0,10 fraction fraction fraction fraction fraction fraction ,05 0, Fractions starting sample hb-pu-ph
4 2-dimensional separation A 2 +B 3 Poly(urea-urethane)s hb-pu-ph n, hb lin-pu Diphenylurea+Li Da n, lin TDI+DEA+phenylisocyanate 398Da fraction 17 0,35 0,30 0,25 fraction 12 m i 0,20 0,15 fraction 10 0,10 0,05 fraction 5 0, Fractions
5 2-dimensional separation A 2 +B 3 Poly(urea-urethane)s n, hb n, hb n, lin hb-pu- hb-pu-ph lin-pu 0.0 lin-pu α= 0.72 log[η] -0.5 hb-pu- α = B-PU-Ph α = logm w
6 2-dimensional separation Branched polymers Elution Fractionation Molar mass
7 2-dimensional chromatography (LCxLC) Branched polymers I SEC elution volume
8 Separation of linear and branched polymer 2D-LC SEC Branched LAC Linear molar mass Branched Linear Coelution in SEC elution volume [ml] Separation in the 2 nd Dimension
9 Sample Pump 2 nd D Pump 1 st D Gradient Chromatography: Two-Dimensional Liquid Chromatographic Set-up normalized ELSD Signalintensity [%] D-LC Waste SEC Separation: ydrodynamic Volume Elution volume [ml] ELSD
10 Pump 1 st D Sample Pump 2 nd D ELSD Waste Detector Intensity
11 2-dimensional chromatography (LCxLC) Branched polymers n-line 2D separation of a mixture of PS star polymers having an arm molecular weight M arm = 4800 and polydisperse polystyrene adke, e-polymers, 2005
12 Separation of linear and branched polymer Liquid chromatography at critical conditions LCCC Si n molar mass SEC LAC 6x10 4 5x10 4 SY-0 SY-18 SY-38 SY-50 elution volume [ml] M W / g mol -1 4x10 4 3x10 4 2x % acetone: 6% TF At critical conditions of the linear polymer, LAC separation according to branching! Location of the end groups and compaction of the molecule responsible B elution volume / ml Macromolecules 2010, 43,
13 Separation of linear and branched polymer 2D-LC hyperbranched, DB = 50% V e, GLAC linear, DB = 0% Si n pseudo-dendrimer, DB = 100% molar mass, g/mol V e, GLAC linear, DB = 0% Macromolecules 2010, 43, molar mass, g/mol
14 Phase Distribution Chromatography What is Phase Distribution Chromatography? First publication in the year 1970 from Casper and Schulz (Mainz) [.. Casper, G.V. Schulz; J. Polym. Sci, Part A-2; (1970); 8; ] Developed for determination of molecular weight distribution of narrow distributed Polystyrenes Experiment of dynamic phase separation PDC equipment Mainz
15 Phase Distribution Chromatography Thermodynamic-kinetic interactions between Mobile Phase Diluted solution of polymer to be separated Stationary Phase Gel of same polymer, linear, high molecular, non-crosslinked Below theta-temperature (Cyclohexane Polystyrene 34 C) within the solubility gap Curves of 2 Polystyrenes (Mw = 135,000 and 415,000 g/mol) depending on temperature (1970) 4
16 First Separations First Experiments of Fractionation C / polymer blends Mobile phase: cyclohexane (C, θ-solvent), polymer solution (1 wt%) flow rate: ml/h Stationary phase: concentrated ultra high molecular polystyrene (UPS) adhering at Ballotini (glass beads, Ø = 0.1 mm) insoluble below 36 C, non crosslinked M w = 5,800,000 g/mol PDI = 1.16 fractions Column: Length = 26 cm Ø = 1.3 cm 5
17 Preparation of stationary phase SEM images of pure and coated Ballotini made with Phenom (Fei Company) Compositional mode Compositional mode 160 µm wt% of UPS = 0.25 % Frequent changes of solvent / non-solvent Flushing with C (loss of 20 %) Topographic mode Topographic mode 6
18 First Separations: Preliminary Tests Mixture (1:1) of two linear polystyrenes PS1: M w = 125,000 g/mol; PDI = 1.01 PS2: M w = 300,000 g/mol; PDI = 1.01 Fractionation at ambient temperature (23 C) Composition of each fraction determined by SEC-I-signals Preliminary test 2: Separation according to molar mass? concentration (mg/ml) 1,0 0,8 0,6 0,4 0,2 0,0 Distribution of polymer concentrations during fractionation V C (ml) percentage of PS (%) atios of PS1 and PS2 in fractions determined by GPC-I signals V C (ml) Separation according to MM! 125k 300k 9
19 First Separations: Preliminary Tests Distribution of polymer concentrations during fractionation Preliminary test 3: Influence of stationary phase? concentration (mg/ml) 0,5 0,4 0,3 0,2 0,1 0, V C (m l) o separation effect using pure Ballotini without UPS! percentage of PS (%) atios of PS1 and PS2 in fractions determined by GPC-I signals V C (ml) 125k 300k 10
20 Turbidimetric measurements Equipment for cloud point determination Thermometer Pt100 PC Multimeter Photo diode Thermostat Laser Magnetic stirrer 11
21 Turbidimetric measurements 1,0 5 wt% star-shaped PS Turbidimetric measurements Solvent: Cyclohexane Linear polystyrene (M w = 300,000 g/mol; PDI = 1.01) Star-shaped polystyrene; 3 arms (M w = 305,000 g/mol; PDI = 1.06) Cooling rate: 0.1 K/min I/I o 28 0,8 5 wt% linear PS 0,6 Inflection point 0,4 0,2 0, T( C) Linear PS Star-shaped PS Polymer content (wt%) inflection point T( C) Polymer content (wt%) inflection point T( C) T ( C) C linear C star Determination of preferential concentration and temperature! polymer content (wt%) 12
22 Upscale: Separation of linear and star-shaped Polystyrene Using a system with PLC pump, column (300 x 7.5 mm), I- and UV-detector (λ = 280 nm) First measurements with low concentration (0.2 wt%) to determine flow rate and injection volume Checking elution times of Polystyrenes with different molar masses (flow rate 14 ml/h, temperature 24 C) UV - signal (V) 0,08 0,06 0,04 0,02 0, retention time (min) PS 2k PS 19k PS 92k PS 233k PS 300k molar mass (g/mol) 3x10 5 2x10 5 1x k, 8 arms 77k, 4 arms 300k, 3 arms Linear PS Star shaped - PS 0 4,4 4,8 5,2 5,6 6,0 retention volume (ml) Separation according to branching! 15
23 Upscale: Separation of linear and star-shaped Polystyrene Tempreature dependent separation according to branching!
24 Amphiphilic polymers drug p < 7 encapsulation release -C -C C- C- C- -C C- -C C- -C C- -C C- -C C- C- C- C- -C -C -C -C C- C- C- -C -C -C -C C- -C -C -C C- C- C-
25 Amphiphilic polymers with hb core Br Br Br Br Br Br Br epoxy photocuring C C isocyanato thermocuring
26 a.u. monomer conversion [%] Star Formation Br m 1.) 100 eq. PhC, 100 C, 6 h n,hb 2.) PhC, 100 C 10 min n,hb h: 75% monomer conv. died living-chain-ends start 2 h 6 h 18.5 h 22.5 h 18.5 h: 74% monomer conv. 6 h: 47% monomer conv. 2 h: 17% monomer conv elution volume [ml] SEC in DMAc + 3 g/l LiCl time [h]
27 Star growing Br m 1.) 100 eq. PhC, 100 C, 6 h n,hb 2.) PhC, 100 C 10 min n,hb 1,0 normalized I signal normalized UV signal 0,8 hyperbranched star nomalized signal I and UV 0,6 0,4 0,2 polyoxazoline chains grown from impurities 0,0 6,5 7,0 7,5 8,0 8,5 9,0 9,5 10,0 elution volume [ml]
28 Star dimerization FD277cap_01 (Y1) FD278capw_01 (Y1) 0.5 M K/ Et+1% 2 90 LS signal ( volt ) 0,03 0,02 0,01 0, elution volume ( ml )
29 Amphiphilic nanocarrier 0,4 2 I-Signal LS-Signal 0,2 0,0 6 8 Elutionsvolumen [ml] 0,020 0,015 0,010 0,005 0,000 I-Signal [V] LS-Signal [V] M n 2000 g/mol M w 2600 g/mol dn/dc DMAc LiCl 3 C 2 0, I-Signal M/EV-Abhängigkeit 0,6 0,5 M n g/mol M w g/mol dn/dc DMAc LiCl LS-Signal 0, , , , , Elutionsvolumen [ml Molekulargewicht [g/mol] LS-,I-Detektor [V] n T, 72 h DMF 3 C n 6
30 PEI poly (glutamic acid ester) core-shell I-Signal M/EV-Abhängigkeit Elutionsvolumen [ml] Molekulargewicht [g/mol] LS-,I- Detektor [V] LS-Signal I-Signal M/EV-Abhängigkeit Elutionsvolumen [ml] Molekulargewicht [g/mol] LS-,I- Detektor [V] DMF 50 C, 72 h n 2 n M n g/mol M w g/mol dn/dc DMAc LiCl 2 LS-Signal M n 7600 g/mol M w g/mol dn/dc DMAc LiCl
31 PEI poly (hydroxy ethyl glutamin) core-shell 2 n 2 n C, 72 h 2 n 2 n Aminolysis I-Signal LS-Signal M/EV-Abhängigkeit Molekulargewicht [g/mol Elutionsvolumen [ml] g/mol 0.20 LS-,I-Detektor [V] A4F M n g/mol M w g/mol dn/dc
32 PEI poly (L- glutamic acid) core-shell 2 n 2 2 n a Me/ 2 (1:1) a n I-Signal LS-Signal M/EV-Abhängigkeit Elutionsvolumen [ml] n Molekulargewicht [g/mol] LS-, I-Detektor [V] ydrolysis PEI PEI-PLGA p U [mv]
33 Complex dendritic polymers and their interactions for biological applications J. Chromatogr. A 2010, 1217, Polym. Prepr.(ACS) 2010, 51 (2), orgchem.science.ru.nl
34 Glycopolymer Multifunctional macromolecules for potential polymeric therapeutics and diagnostics Specific interactions e.g. with proteins and polypeptides Transport molecules for metal ions and particles, A und DA molecules Exploration/tailoring of biological processes ecognition/non-recognition of oligosaccharide-modified molecules on cell membrane surfaces Formation of biocompatible surfaces hb polymers dendrimers linear polymers spherical globular compact worm-like polymers coil-like polymers
35 1 st generation MI copolymer 2 nd generation MI copolymer 3 rd generation MI copolymer = Dendronised MI copolymers decorated with maltose shell maltose epeating units of MI copolymers with dendritic lysine side groups for use as bio-hybrid structures in solution and in thin layer technology
36 14 applications: molecular containers guest-host interactions drug-delivery systems biomimetic materialien synthetic nanoparticles tailored catalytic systems Topology linear main chain (maleimide-ethylene-copolymer) modified end groups with maltose poly-l-lysin-dendrones in 4 generations ( ) ( ) ( ) ( ) ( ) ( ) ( ) ( ) ( ) ( ) Dendronised Polymers: aggregation behaviour Manuscript in preparation
37 Principle of FFF separation Source: Postnova Analytics Separation in a narrow channel Separation force perpendicular to the solvent flow
38 FFF separation methods Source: Postnova Analytics
39 AF4 separation principle Laminar flow inside the channel Log M Source: Postnova Analytics Size separation: V E ~ h Elution Volume
40 AF4-MALS of dendronised glycopolymers linear F x -gradient broad distributions elution time F f, F x (ml/min) 1,5 1,0 0,5 Fokus/ Injektion Fraktionierung/ Elution linearer F x -Gradient exponentieller F x -Gradient AF4-MALS 50 mm a 3 -Puffer c= 1 mg/ml, p = 5,5 exponential F x -gradient aggregate resolution elution time 0, Elutionszeit (min) radius (nm) MI-G0-Mal MI-G1-Mal MI-G2-Mal MI-G3-Mal I and LS signal (90 ) (V) molar mass (g/mol) MI-G0-Mal MI-G1-Mal MI-G2-Mal MI-G3-Mal I and LS signal (V) elution time (min) elution time (min)
41 AF4-MALS of dendronised glycopolymers aggregation number (M w /M w,0 ) p = 3.5 p = 5 p = 7 p = 8.5 p = generation number no aggregation in 1st and 2nd generation strong aggregation at low and high p of 0 and 3th generation 16
42 Molecular Dynamic simulation of MI-G0-Mal C 2 C 2 C C = 200 repeating units elical structure calculated 17
43 AF4 Untersuchungen der Glykopolymere AF4-MALS of dendronised glycopolymers Scaling parameter ν: g = KM ν log( g ) (nm) for MI-G0-Mal: 2,5 2,0 1,5 p = 3,5 p = 7 p = 11 y=-0,26x 2 +1,17x+1,29 y=0,98x+1,31 y=0,67x+1,18 y=0,25x+1,27 1,0 0,0 0,5 1,0 1,5 2,0 2,5 log(m w *10-6 ) (g/mol) ν > 1 stiff rod ν = 0,5-0,7 coil in a good solvent ν = 0,33 hard sphere W.Burchard, Advances in Polymer Sciences, Vol
44 Mikroskopie AFM of aggregates of 3rd generation dendronised glycopolymers 48 nm 88 nm 165 nm 167 nm 20
45 Dendritic delivery systems Core-shell polymers - Capped (Meijer) dendrimer box Guest molecules remain well within the interiour of the box. Additional capability: guest molecules can be entrapped by the shell. Crosslinked dendritic polymers A new way to deliver drugs in the cavities among dendritic molecules. Uncapped dendrimer box Guest molecules exhibit Brownian motion and are not strongly coupled. Collaboration Dr. Appelhans Multi-shell Core-shell structure Additional capability to entrap different types of guest molecules (hydrophilic and hydrophobic) as well as tune physico-chemical properties of the polymer.
46 PEI-maltose J Chrom A 2010, 1217, 4841
47 L PEI-maltose core-shell = PEI = D 2 Mal (maltose) 2 ose Bengal D PEI L L PEI-Mal
48 PEI-Mal variation PEI PEI 2 M w 5k Da and 25k Da Dense shell Structure A 1 PEI pen shell Mal 1 pen shell Structure B PEI Mal Mal Dense shell Mal = 1: mono- and oligosaccharides eduction agent: B 3 *Py complex pen shell Structure C Maltose A5 PEI-5 kda + Maltose A25 PEI-25 kda + Maltose B5 PEI-5 kda + Maltose B25 PEI-25 kda + Maltose C5 PEI-5 kda + Maltose C25 PEI-25 kda + Maltose Biomacromolecules 2009, 10,
49 PEI-Mal encapsulation ose Bengal pure ose p p Wavelength (nm) Wavelenght (nm) UV-Vis absorption maximum for pure ose Bengal at p 6.7: λ = 550 nm
50 Where are the guest moelcules? Low complexation ratio drug:pei-mal complexation in PEI core 1,0 0,8 Vis spectra of ose Bengal Low complexation ratio B in water B in ethylamine sol igh complexation ratio drug:pei-mal complexation in PEI core and maltose shell Absorbance 0,6 0,4 0,2 1:1 complex B:B25 0, Wavelenght [nm] 1,6 1,4 1,2 igh excess of B B in maltose solution Absorbance 1,0 0,8 0,6 0,4 0,2 B in water 30:1 complex B:B25 0, Wavelenght [nm]
51 Separation of B and B@PEI-Mal Focus flow Injection Focus flow Membrane
52 Separation of B and B@PEI-Mal Focus flow Focus flow Membrane
53 Quantitative determination of free B Injected ose Bengal (µg) LS, AUX (volts) Chromatograms B Konzreihe 2 C05 5kD 3... B Konzreihe 2 C07 5kD 2... B Konzreihe 2 C085 5kD_... B Konzreihe 2 C12 5kD_0... B Konzreihe 2 C17 5kD 2... B Konzreihe 2 C20 5kD_ Volume (ml) Injection/detection limits: Minimum = 18 µg Maximum = 80 µg Peak Area Pure ose Bengal solutions with different concentrations prepared from stock solution (3 injections; 100 µl) Method: Focus Flow 3 ml/min for 20 min; UV detector (550 nm) at cross flow outlet Eluent: pure water (0.02% a 3 ) p 6.4
54 Membrane modification with free B 5 crossflow injection flow 1.0 flow rate (ml/min) filtration/ focussing fractionation/ elution elution time (min) injection flow rate (ml/min) peak area of UV-signal Method: Focus Flow 3 ml/min for 20 min; UV detector (550 nm) at cross flow outlet (waste line), Eluent: pure water (0.02% a 3 ) injected B (50 µg) injected B (100 µg) injection number epeated injections of pure ose Bengal solution: 250 µg needed to modify the membrane); stable B layer formation
55 UV esponse (V) eproducibility tests with free B µl 100 µl 200 µl Elution Time (min) Injected volume (µl) Injected mass (µg) UV peak area Calculated mass (µg) Variation of injected volume at same B solution concentration (0.33 mg/ml)
56 Comlexation kinetics 1 : 169 = PEI-Mal : B 1.0x10 6 molar mass (g/mol) 8.0x x x x10 5 M w M n molar mass (g/mol) Zeit (min) 5.0x x x10-8 bounded ose Bengal isolated ose Bengal standard deviation < 2% 2.0x time (min) stable B@PEI-Mal complexes over 630 min
57 Complexation studies of B and PEI-Mal determined B:PEI-Mal B quantity by UV-detection calc from M n increase (MALLS) injected B:PEI-Mal 0 J Chrom A 2010, 1217, 4841
58 determined B:PEI-Mal Complexation studies of B and PEI-Mal B@PEI 25K-Mal B B@PEI 5K-Mal B B@PEI 5K-C11-Mal A injected B:PEI-Mal
59 TAKS Susanne Boye Dietmar Appelhans Petra Treppe Christin oßberg ikita Polikarpov Frank Däbritz
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