CHARACTERIZATION OF BRANCHED POLYMERS

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1 CHARACTERIZATIN F BRANCHED PLYMERS verview: Properties Branching topology Branching degree Albena Lederer Leibniz-Institute of Polymer Research Dresden Member of Gottfried Wilhelm Leibniz Society WGL Hohe Strasse 6, D Dresden, Germany

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3 Branching architectures AK Prof Müller

4 Branching architectures Topologies linear hyperbranched polymers stars dendrimers short chain branching (SCB) comb polymers (eg long chain branching, LCB) networks eg, microgels

5 Branched vs Linear Properties linear polymers branched polymers cristallinity molar mass distribution viscosity amorphous coils or ordered chains does not change with the molar mass (free radical polymerisation or linear polycondensation) high viscosity low crystallization increases with molar mass low viscosity functionallity lower with the molar mass higher with the molar mass

6 Branched architectures Synthetic ways vs MMD Free radical polymerisation and polycondensation high molar mass distributions (MMD,M w / M n ) long and short chain branching in polyolefins (electron beam irradiation, chain-walking, metalocen catalysis);graft copolymers (star, comb) (if controlled lower MMD) M w / M n M w ( for linear polymers M w / M n = 2 acc Schulz-Flory Distribution) Living polymerisation low molar mass distributions Stars, comb polymers (for linear even M w / M n 1 + M 0 /M n ) ne-pot polycondensation high MMD hyperbranched polymers (AB 2 or A 2 +B 3 ) with M w / M n M w 1/2 Multistepp polycondensation no MMD dendrimers with M w / M n = 1

7 Branched architectures in the nature A typical amylopectin molecule has about 1,000 glucose molecules arranged into branched chains with a branch occurring every 24 to 30 glucose units Complete hydrolysis of amylopectin yields glucose; partial hydrolysis produces mixtures called dextrins, which are used as food additives and in mucilage, paste, and finishes for paper and fabrics Glycogen is an energy reserve in animals, just as starch is in plants Glycogen is similar in structure to amylopectin, but in a glycogen molecule a branch is found every 12 glucose units Glycogen is stored in the liver and skeletal muscle tissues First observations Staudinger in 1937 First expanded characterizations from W Burchard, 1960-

8 Branched architectures Characterization First observations Staudinger 1935 Polyethylen branching dependend on pressure 1940 (LCB, SCB) Flory 1943 first theoretical calculations on kinetics of gelation and statistical branching Characterization of branching is generally based on qualifying the particular properties of branched macromolecules: Decrease of the size (increase of the density) of the branched compared to the linear molecules at the same molar mass: M lin = M HB V h, lin > V h, HB M lin < M HB V h, lin = V h,hb Influence on radius of gyration and viscosity!!!

9 Branched architectures Characterization First observations Staudinger 1935 Polyethylen branching dependend on pressure 1940 (LCB, SCB) Flory 1943 first theoretical calculations on kinetics of gelation and statistical branching Characterization of branching is generally based on qualifying the particular properties of branched macromolecules: Decrease of the size (increase of the density) of the branched compared to the linear molecules: Flory-Fox equation [η] M = φ R 3 Radius of gyration Universal constant Molar mass Intrinsic viscosity Developed for linear and some (less) branched polymers (LCB) by Zimm-Stockmayer, 1949 Fractal dimension, d f leads to more correct classification of branched polymers

10 Branched architectures Characterization methods In solution Light Scattering (R g, R h, A 2,M w ), Size Exclusion Chromatography (M w, M n ), Viscosity ([η]) Informations about: Contraction factors: g = R 2 g, branched / R 2 g, linear (linear and branched polymers of g = [η] branched / [η] linear the same chemical character) Controlled by molecular architecture, excluded volume, intermolecular hydrodynamic interactions Molar mass dependencies, ie Conformation, Shape, Scaling parameters In Bulk rheological characterization scillatory Shear Flow, Uniaxial Elongation Flow Information about entangled dynamics and melt flow Identification of branches is very sensitive but only qualitative Spectroscopy NMR, FTIR Information about branching frequency in SCB polymers and degree of branching in hyperbranched polymers Simulation Numerical simulations: Monte Carlo, Molecular dynamics, Brownian dynamics Information about equilibrium and dynamic behaviour and rheological and hydrodynamical properties of simple polymer systems

11 Branching topology Regularly branched star polymers f = functionality of the core = branching parameter f=3 f=4 linear chain with m units f=6 - Global parameters of non linear polymer - Internal structure can be easilly characterized by spectroscopy (comprable to linear structures)

12 Branching topology Regular comb polymers m f = number of side chains n short side chains (like substituted linear chain) short backbone (like star polymer)

13 Branching topology Dendrimers f = functionality of the branching unit g1 g 2 g 3 g 4 g 1 g 2

14 Branching topology Randomly branched systems Flory ideal randomnes: - all functional groups have the same reactivity, independent on molar mass - ring formation is excluded Extent of reaction: α = Number of reacted functional groups Number of all functional groups Fully random systems are treated by random statistics (eg Gauss statistic) from Burchard,W Adv Polym Sci 143, 1999

15 Branching topology Hyperbranched systems AB (f-1) polycondensation: A can react only with B Extent of reaction of A-groups α = 0 to 1 Extent of reaction of B-groups β = α / (f - 1) No gelation! from A B B B 1 from A, where B 1 and B 2 have different reactivity B 2 longer linear chain sections!

16 Branching degree Long chain branching Branching ratio Radius Method or Viscosity Method (contraction factor) R 2 g, branched g = 2 Rg, linear at the same M [ η] g' = [ η] branched linear at the same M 1,0 where 0 < g <1 Influence of b on g Branching ratio Mass Method M g = M linear branched ( a+1) b at the samev g = (M linear /M branched ) (a+1)/b 0,8 0,6 0,4 0,2 a = 0,7, b= 0,5 a = 0,7, b= 1 a = 0,7, b= 1,5 0,0 0,0 0,2 0,4 0,6 0,8 1,0 where b is a drainage parameter with values M linear /M branched between 0,5 and 1

17 Branching degree Long chain branching Determination of g for randomly branched polymers (Zimm and Stockmayer, 1949) Trifunctional branching Polydisperse g 3 1/ 2 1/ 2 1/ B (2 + B) + B = ln 1 1/ 2 1/ 2 B 2 B (2 + B) B Monodisperse g 3 1/ 2 B 4B = π 1/ 2 Tetrafunctional branching Polydisperse g 4 = ln(1 + B B) Branching per molecule, B Monodisperse g 4 1/ 2 B 4B = π 1/ 2

18 Branching degree Branching per molecule, B Long chain branching Influence of B on g branching ratio, g 1,0 0,8 0,6 0,4 0,2 4-functional polydisperse 4-functional monodisperse 3-functional monodisperse 3-functional polydisperse Long chain branching per 1000 repeat units M λ =1000B 0 M repeat unit molar mass 0,0 0,01 0, branching per molecule B molar mass of a branched polymer

19 Characterization of branching Long chain branched polyolefins SEC 1,2,4-trichlorobenzene, 150 C, flow rate 10 ml/min, 2 columns PL-mixed-B-LS, RI detector Relative (linear standard calibration) Iterative (external [η]) Absolute (LS detector)

20 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation

21 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation polymer logm size exclusion adsorption SEC separation solvent column material elution volume

22 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation

23 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation I (RI, UV, LS, Visco) elution time (elution volume)

24 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation M Peak elution time (elution volume)

25 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation M peak I elution time (elution volume)

26 Characterization methods SEC Size Exclusion Chromatography (SEC) = molar mass determination on the basis of molecular size separation I M n M w M z molar mass A Lederer

27 Characterization methods Multi Angle Laser Light Scattering (MALLS) detection R θ ( I = θ I I LM θ 0 V ) R 2 Static Light Scattering isotrope scattering d << λ/20 anisotrope scattering d λ/20

28 Multi Angle Laser Light Scattering (MALLS) detection M c N dc dn n R L λ π θ = = c A c A M R c K θ K = i i i c M c K R ) ( lim 0 θ w i i i i i c M M c c R c K 1 ) ( lim 0 = = θ Characterization methods Static Light Scattering

29 Multi Angle Laser Light Scatterinng (MALLS) detection M c N dc dn n R L λ π θ = = c A M w R c K θ 0 ) ( = = θ θ θ I I P c A P M R c K w 2 ) ( = θ θ 2 sin ) ( θ λ π θ z r G P + = K Characterization methods Static Light Scattering

30 Degree of branching For AB2 polycondensation D=dendritic units, two B functionalities reacted L=linear units, one B functionality reacted T=terminal units, no B functionality reacted Determination of degree of branching via 1 H-NMR: DB Fréchet = T+L DB Frey = T+L+D 2D 2D+L DB Fréchet suitable for higher molar masses DB Frey also for oligomers 1 H NMR signals fraction DB Fréchet DB Frey Aryl-H F6 0,54 0,45 1D 2T F9 0,54 0,47 2D 2L F11 0,55 0,51 1L1T F13 0,56 0,52 F15 0,56 0,52 H N H H H NH H NH H H N HN NH H Hyperbranched polymers H H H N H NH HN H D H N HN H NH H N H N NH = H HN NH H H N N L H H H H N H N n,hb H H T NH hyperbranched poly(etheramide) H -NH DLT (ppm) F6 0,56 0,48 F9 0,57 0,50 F11 0,57 0,53 F13 0,56 0,53 F15 0,56 0,54 Branching fraction FB D 1 = = DB 2D + L 2 = N 1000

31 The molar mass determination of hb structures LS UC DRI/PS DRI/PE

32 Sepration of HB aromatic polyester with H end groups H C RI, LS [V] n, hvz 0,30 0,25 0,20 0,15 0,10 Mw = g/mol Mw/Mn = 2,0 Z n = approx 85 RI LS 90 Molar mass Solvent: THF PLgel mixed B column dn/dc = 0,25 ml/g column-polymer interactions Molar mass [g/mol] 0, , Volume [ml]

33 Sepration of hyperbranched aromatic polyester with H end groups H C n, hvz Mw = g/mol Mw/Mn = 2,0 Z n = approx 85 Solvent: DMAc+ LiCl (2g/L) PLgel mixed B column dn/dc = -0,275 ml/g N column-polymer interactions up to g/mol Molmasse [g/mol] ,5 5,0 5,5 6,0 6,5 7,0 7,5 8,0 Elutionsvolumen (ml)

34 Asymmetric Flow Field Flow Fractionation (A4F)

35 Asymmetric Flow Field Flow Fractionation (A4F) M n M w M z I (detection: RI, UV, LS, Visco) elution time (elution volume)

36 Sepration of hyperbranched aromatic polyester with H end groups H C n, hvz Solvent: THF A4F channel dn/dc = 0,25 ml/g Membrane cut-off 5 kda Flow (ml/min) Inject/ Focus cross/focus flow inject flow Elution 0,8 0,6 0,4 0,2 Mw = g/mol Mw/Mn = 2,0 Z n = approx 140 RI, LS signal [V] RI LS 90 0,4 Molar mass 0,3 0,2 0, ,5 0, Molar mass [g/mol] 0 0, Mw = g/mol Mw/Mn = 4,5 Z n = approx 250 RI, LS 90 [V] 0,3 0,2 0,1 RI LS 90 Molar mass elution time (min) Molar mass [g/mol] 0, Volume [ml] , Volume [ml] 10 2

37 Flow (ml/min) Sepration of hyperbranched aromatic polyester with H end groups Inject/ Focus cross/focus flow inject flow Elution 0,8 0,6 0,4 0,2 Solvent: THF A4F channel dn/dc = 0,25 ml/g Membrane cut-off 5 kda Flow (ml/min) Inject/ Focus cross/focus flow inject flow Elution 0,8 0,6 0,4 0,2 0 0, Mw = g/mol Mw/Mn = 3,3 0,5 0,4 elution time (min) RI LS 90 Molar mass , Mw = g/mol Mw/Mn = 4,5 Z n = approx 250 elution time (min) RI 0,5 LS 90 Molar mass , RI, LS 90 (V) 0,3 0,2 0, Molar mass [g/mol] RI, LS 90 [V] 0,3 0,2 0, Molar mass [g/mol] 0, elution time (min) , Volume [ml] 10 2

38 Characterization of branching Long chain branched polyolefins SEC 1,2,4-trichlorobenzene, 150 C, flow rate 10 ml/min, 2 columns PL-mixed-B-LS, RI detector Relative (linear standard calibration) Iterative (external [η]) Absolute (LS detector)

39 Characterization of branching Long chain branched polyolefins absolute MM-determination SEC LS I i ~ M i RI I i ~ C i Data Processing AS1, AS2 Wyatt MMD, LCB, R g

40 Characterization of branching Long chain branched polyolefins MM-determination via iterative calculation method SEC RI I i ~C i [η] ext Wyatt Data processing & Iterative calculation MMD, LCB, a

41 Molar mass characterization methods Iterative calculation method Inputs Postulates C i log[η] i M i V ei = f([η] i M i ) [η] br i = KM ia g b (Kuhn-Mark-Houwink) log[η] i V ei V ei g b = [η] br i / [η] lin i = f (λ i M i ) λ i = B i / M i = const [η] ext lin = KM a lin logm i [η] ext B, number of branches per molecule g b, branching ratio A Lederer

42 Characterization of branching Long chain branched polyolefins Iterative calculation method Calculation [η] calc = Σ m i [η] i If [η] calc = [η] ext linear polymer If [η] calc > [η] ext LCB polymer iteration from λ LCB

43 Characterization of branching Long chain branched polyolefins Investigated Systems PPL linear PP commercial product PPB-a branched PP PPL after e - -beam irradiation PPB-b PPB-1 branched PP commercial product PPB-2 HDPE linear PE commercial product LDPE branched PE commercial product

44 Characterization of branching Long chain branched polyolefins Investigated Systems PPL linear PP commercial product PPB-a branched PP PPL after e - -beam irradiation PPB-b PPB-1 branched PP commercial product PPB-2 HDPE linear PE commercial product LDPE branched PE commercial product mean square radius of gyration [nm] molar mass [g/mol] initial PP 20 kgy 60 kgy 100 kgy 150 kgy

45 Characterization of branching Long chain branched polyolefins Investigated Systems PPL linear PP commercial product PPB-a branched PP PPL after e - -beam irradiation PPB-b PPB-1 branched PP commercial product PPB-2 HDPE linear PE commercial product LDPE branched PE commercial product

46 Characterization of branching Long chain branched polyolefins conv SEC SEC-LS iteration M n M w M n M w M n M w PPL PPB-a PPB-b PPB PPB HDPE LDPE

47 Characterization of branching Molar Mass Characterization via Conventional SEC SEC-LS-as1 SEC-iteration Long chain branched polyolefins molar mass, M w [g/mol, x10-3 ] PPL HDPE PPB-a PPB-b PPB-1 PPB-2 LDPE rel deviation of M w compared to LSas2

48 Characterization of branching Long Chain Branching via Long chain branched polyolefins SEC-iteration SEC-LS-as1 Long chain branhcing per 1000 monomer units 3,5 3,0 2,5 2,0 1,5 1,0 0,5 0,0 PPL HDPE PPB-a PPB-b PPB-1 PPB-2 LDPE

49 Characterization of branching Long chain branched polyolefins Long Chain Branching results comparison between SEC-LS and iterative method 4,0 1,0 branches per 1000 monomers 3,5 3,0 2,5 2,0 1,5 1,0 Iteration LS as2 [η] calc [η] ext LCB/10 3 monomers LCB/10 3 monomers PPL PPBa PPBb ,9 0,8 0,7 0,6 0,5 0,4 0,3 0,2 cum weight fraction 0,5 0,1 0,0 0,0 1,00E+03 1,00E+04 1,00E+05 1,00E+06 1,00E+07 1,00E+08 molar mass ( g/mol )

50 Degree of branching Dendritic polymers 100% degree of branching of dendrimers is defined by their step wise synthesis Divergent: + Deprotection Degree of branching (DB)=100% I dendrimer II D T Convergent: + III II dendron

51 Degree of branching Hyperbranched polymers 50% degree of branching for polycondensation of AB 2 polymers is theoretically predicted by Flory if: - A can react only with B - all B groups have the same reactivity independent on molar mass - no ring formation and other side reactions ne-pot polycondensation: + n L D Degree of branching (DB)=ca 50% T

52 Degree of branching Hyperbranched polymers 1 H NMR of hyperbranched poly(etheramide) in DMS-d H T L NH D L T 1D,3T 3L,5L 1L1T 9D9L 3D 8 Terminal H H 2 2T 3T 1T DMS 4T NH H 7T 8 2D 3D 1D 9D 4D NH 7D 8 Linear H 2L 3L 1L 9L 4L NH 6L x 5L 7L 8 x= N-methylcaprolactame x x x Dendritic δ in ppm

53 1 H NMR of hyperbranched aliphatic-aromatic polyester in DMS-d 6 H Degree of branching Hyperbranched polymers C H CH 3 n, hb H C H H T H 3 C H H C CH 3 C D H 3 C CH 3 C C CH 3 C C CH 3 H C C CH 3 H 3 C H L H

54 Degree of branching Hyperbranched polymers 1 H NMR of hyperbranched aliphatic-aromatic polyester in DMS-d 6 CH (ppm) H H H 1180 H H H 2 DMS-d 6 CH 2 CH2-CH DP = I N NMR N H number of specific groups per repeating unit H 1 p a =1 DP 1 DB Frey = p a δ (ppm) p a = 0,931; DB Frey = 0, CH 3 00 M n = DP M 0

55 Degree of branching 9/18 6/15 7/16 8 /17 7 /16 8/17 Hyperbranched polymers 1 9 / δ(ppm) 5/14 3/12 2/11 1/ δ 45 (ppm) δ (ppm) H H H CH C C C C 5 6' H H 7' 8' R2 R 1 13 C NMR of hyperbranched aliphatic-aromatic polyester in DMS-d H H CH C C C C 15' 14 H H 16' 17' R2 9' 18' R 3 R 3 DB Fréchet = T+L 2D =0,45 DB Frey = =0,47 T+L+D 2D+L

56 Hyperbranched polyphenylenes - variations 4+2 (Diels Alder) cycloaddition reaction with subsequent decarbonylation R R R + Diphenyl ether 230 C 48 h Ph Ph Ph Ph Ph Ph - C R R R A: fully phenylated cyclopentadienone - B: fully phenylated alkyne A 2 AB 2 AB B 3

57 Hyperbranched polyphenylenes - variations +B +B A A A a a a A 2 Aa a 2 B B B b b +A +A +A B B B b b b b B 3 B 2 b Bb 2 b 3 DB = 2D 2D + L = 2( b 3 2( b ) + 3 ) ( Bb 2 )

58 Hyperbranched polyphenylenes polymer synthesis hb AB 2 polyphenylenes - pol#ymer backbone: hexaphenylbenzene units - linked in 1, 2 & 4 position - via para-substituted phenyl rings n Ph 2, 230 C Monomer reaction time [h] yield [%] M w [g/mol] M w /M n T at 10% weight loss [ C] AB AB AB

59 Hyperbranched polyphenylenes polymer synthesis hb A 2 +B 3 polyphenylenes - linked in 1 & 3 or 1 & 4 position - phenyl ring from A 2 via para position n Ph 2, 230 C - phenyl ring from B 3 1,3,5- substituted m monomer ratio A 2 + B 3 reaction time [h] yield [%] M w [g/mol] M w /M n T at 10% weight loss [ C] 1 : : : : no glass transitions up to 360 o C

60 Hyperbranched polyphenylenes characterization hb AB 2 and AB 2 +AB polyphenylenes - AB 2 broad signals - restrained rotation AB C 6 C a' e a b d c - +AB less broad & higher intensities - more linear units a'' f g n,hb - focal unit not detected - 2 ethyne signals from T and L units with similar intensities - statistical polymerization AB 2 +AB (1:1) higher signal intensities - no quantification of T, L & D units or AB content possible

61 Hyperbranched polyphenylenes characterization hb A 2 +B 3 polyphenylenes: 13 C NMR 1:1 3:2 3:1 terminal unit (B 2 b) linear unit (Bb 2 ) dendritic unit (b 3 ) terminal unit (Aa) linear unit (a 2 ) R R R R R R R R R R R R

62 Hyperbranched polyphenylenes characterization - higher structural variability than AB 2 assignment T, L & D possible - signal overlap quantification only for T, L and A & B content possible - D unit in spectra under-represented - comparison with theoretical calculations: amount of L increased amount of D decreased S 2 C - 3 rd B group reacts very slowly due to - steric hindrance - (verified by T dependent NMR) T = K S 1 B' ' A' I' I B A - no crosslinking C C - mostly linear - backbone with - A or B terminated - side groups monomer ratio A 2 + B 3 M w [g/mol] ratio of A : B functionalities ratio of B 2 b (T) : Bb 2 (L) groups 1 : : : 68 3 : : 3 5 : 95 2 : : 2 5 : 95 3 : : 1 only Bb 2

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