Low temperature RAFT/MADIX gel polymerisation: access to controlled ultra-high molar mass polyacrylamides
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1 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 Eletroni upplementry Informtion Low temperture RAFT/MADIX gel polymeristion: ess to ontrolled ultr-high molr mss polyrylmides Emmnuelle Red, Aymeri Guinudeu, D. Jmes Wilson, b Arnud Cdix, b Frédéri Violleu nd Mthis Destr * Contents of the upplementry Informtion doument: I. Experimentl etion... 2 A. RAFT/MADIX synthesis of AM-bsed polymers... 2 B. RAFT/MADIX synthesis of DMA-bsed polymers... 3 C. Instrumenttion nd mesurements:... 4 II. Mro-MADIX gents hrteriztion... 5 A. PAM 7 -XA B. P(AM-stt-AMP) 7 -XA C. PDMA 7 -XA III. Molr msses results... 8 A. Homopolymers... 8 B. AMP-bsed sttistil opolymers... 8 Université Pul btier, Lbortoire Heterohimie Fondmentle et Appliquée, UMR-CNR 5069,Bt 2R1, 118 route de Nrbonne,31062 Toulouse Cedex9, Frne,. Fx: +33 (0) ; Tel:+33 (0) E-mil: destr@himie.ups-tlse.fr b olvy Novere, Reserh nd Innovtion Centre - Pris, 52 rue de l Hie oq, Aubervilliers Cedex, Frne Université de Toulouse, Eole d Ingénieurs de Purpn, UPP/DGER 115, 75, voie du TEC, BP 57611, F-31076, Toulouse Cedex 03, Frne To whom orrespondene should be dressed : destr@himie.ups-tlse.fr
2 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 I. Experimentl etion Mterils 2,2 -zobisisobutyronitrile (AIBN, Jnssen Chemi, 98%) ws reristllised twie from methnol before use. Arylmide (AM, NF, 50% in wter stbilized with 100 ppm MEHQ), N,N-dimethylrylmide (DMA, Aldrih, 99%), N-isopropylrylmide (NIPAM, Aldrih, 97%), 2-rylmido-2-methylpropne sulfoni id sodium slt (AMP, Aldrih, 50% in wter) were used reeived. -ethyl--(1-methoxyrbonyl)ethyl dithiorbonte gent (Rhodixn A1, olvy), mmonium persulfte (AP, Aros, 98+%), sodium formldehyde sulfoxylte dihydrte (NAF, Aros, 98%) nd L(+) sorbi id (AsA, Aros, 99%), 2,2 - zobis(2-methylpropionmidine) dihydrohloride (V-50, Aros, 98%), ethyl ette (pure for synthesis, Crlo Erb regent), N,N-dimethylformmide (DMF, Aldrih, HPLC grde>99.9%), ethnol (VWR, 99.9%) nd distilled wter were used without prior purifition. A. RAFT/MADIX synthesis of AM-bsed polymers ynthesis of PAM 7 -XA1. Rhodixn A1 (1.69 g, 8.1 mmol) ws dissolved in 5.94 g of ethnol in two-nek round-bottom flsk. Then, AM (8 g, 56.3 mmol), V-50 (69.4 mg, 0.35 mmol) nd distilled wter (4.61 g) were dded. The mixture ws degssed by bubbling rgon for 30 min while stirring. Then it ws heted under rgon tmosphere t 60 C for 3h until the ompletion of the retion. The ethnol ws evported under vuum prior to freeze-drying the smple to give light yellow powder. (AM onversion=100%, M n, RMN =650 ) ynthesis of P(AM-stt-AMP) 7 -XA1. Rhodixn A1 (2.34 g, 11.2mmol) ws dissolved in 6.52 g of ethnol. Then AM (5.40 g, 38 mmol), AMP (5.74 g, 12.5 mmol) nd V-50 (83.6 mg, 0.31mmol) were simultneously dded with 6.52 g of wter. The mixture ws degssed by bubbling rgon for 30 min while stirring. Then it ws heted under rgon tmosphere t 60 C for 3h until the ompletion of the retion. The ethnol ws evported under vuum prior to freeze-drying the smple. (AM onversion>99%, AMP onversion>99%, F AMP =0.245, M n, RMN =700 ) Redox-initited queous RAFT/MADIX polymeriztion of AM. Typilly, the polymeriztion ws performed s follows: AM (8.00 g, 56.3 mmol), 2% wt solution of PAM 7 - XA1 (0.13 g, mmol) were dissolved in 7.88 g of distilled wter nd pled in thermostted bth set t 10 C while bubbling rgon for 30min before injeting simultneously 0.1 ml of 0.3% wt solutions in wter of AP nd NAF. The retion ws let t 10 C under strem of rgon for 2h until ompletion of the retion (AM onversion>99.9%, M n,ec = , Ð=1.12, dn/d=0.185 ml g -1 ) Redox initited queous RAFT/MADIX sttistil polymeriztion of AM nd AMP. AM (4.25 g, 29.9 mmol), AMP (4.58 g, 9.9 mmol), 5% wt solution of P(AM-stt-AMP) 7 -XA1 (0.05g, mmol) were dissolved in 8.65 g of distilled wter nd pled in thermostted bth set t 10 C. For 30 min, it ws degssed by bubbling rgon before injeting simultneously 0.42 ml of 0.3% wt queous solutions of AP nd NAF. The retion ws let t 10 C under strem of rgon for 2h until ompletion of the retion (AM onversion>99%, AMP onversion>99%, M n,ec = , Ð=1.36, dn/d (P(AM-stt- AMP))=0.147 ml g -1 ) Chin extension. PAM-XA1 (M n,th = ) (0.32 g, 6.65x10-7 mol), AM (0.71 g, 5.00 mmol) were dissolved in 4.48 g of distilled wter nd pled in thermostted bth set t 10 C. For 30 min, it ws degssed by bubbling rgon before injeting simultneously ml of 0.03% wt queous solutions of AP nd NAF. The retion ws let t 10 C under strem of rgon for 2h until ompletion of the retion (AM onversion>99%, M n,ec = , Ð=1.09, dn/d (P(AM))=0.185 ml g -1 ).
3 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 B. RAFT/MADIX synthesis of DMA-bsed polymers ynthesis of PDMA 7 -XA1. N,N-dimethylrylmide (4.98 g, 50.0mmol), Rhodixn A1 (1.49 g, 7.20 mmol), AIBN ( g, 0.07mmol) nd ethyl ette (18.5 g, 210 mmol) were dded t mbient temperture in two-nek round-bottom flsk. The mixture ws degssed by bubbling rgon for 30 min while stirring. Then it ws heted under rgon tmosphere t 60 C for 24h until the ompletion of the retion. Finlly the solvent ws evported under vuum. (DMA onversion=97.6%, M n,rmn =1050 ) Redox initited queous RAFT/MADIX polymeriztion of DMA. PDMA 7 -XA1 5 % wt solution in wter (0.124 mg, mmol), DMA (5.99 g, 60 mmol) were mixed in distilled wter (27.5 ml) in shlenk flsk nd thermostted t 20 C. The mixture ws gently degssed with rgon for 30 min before injeting simultneously 0.75 ml of 1.2%wt queous solutions of AP nd NAF. The retion ws let t 20 C under strem of rgon for 24h until ompletion of the retion (DMA onversion>99.9%, M n, EC = , Ð=1.11, dn/d=0.087 ml g -1 ) Redox initited queous RAFT/MADIX sttistil polymeriztion of DMA nd AMP. For polymeriztion with f AMP =0.09: DMA (6.04 g, 60.9 mmol), AMP (2.76 g, 6.03 mmol) nd PDMA 7 - XA1 5% wt solution in wter (160 mg, mmol) were mixed together in 25.7 ml of distilled wter. The mixture ws gently degssed with rgon for 30 min before injeting simultneously 1.09 ml of 1.2% wt solutions of AP nd NAF. The retion ws let t mbient temperture (T=20 C) under strem of rgon until ompletion of the retion. (DMA onversion=99%, AMP onversion=100%, M n, EC = , Ð=1.61, dn/d=0.154 ml g -1 ). RAFT/MADIX blok opolymeriztion of NIPAM nd DMA: Aqueous ynthesis of PNIPAM-XA1. NIPAM (2.10 g, 18 mmol), PDMA 7 -XA1 (248 mg, 0.23 mmol) nd AP (42.0 mg, 0.18 mmol) were mixed with distilled wter (7.35 ml) in two-nek round-bottom flsk nd thermostted t 25 C during ll the retion. The mixture ws degssed by bubbling rgon for 30 min. Then 2 ml of solution of AsA (32.5 mg, mol) ws injeted under strem of rgon. The retion ws stopped fter 4 hours of stirring t 25 C. The produt ws then freeze dried to give white powder. (NIPAM onversion >99.9%, M n, EC =13 000, Ð=1.28, dn/d=0.087 ml g -1 ). Redox-initited RAFT/MADIX blok opolymeriztion of DMA from PNIPAM-XA1. PNIPAM-XA1 (40 mg, mmol), DMA (4 g, 40 mmol) were pled in shlenk flsk with 11.8 ml of distilled wter nd degssed with rgon for 30 min t 20 C. Then 0.12 ml of 0.6% wt queous solutions of AP nd NAF were simultneously injeted in the mixture. The retion ws let t 20 C under strem of rgon for 24h. (DMA onversion =100%, M n, EC = nd Ð=1.51, dn/d of P(NIPAM-blok-DMA)=0.087 ml g -1 ).
4 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 C. Instrumenttion nd mesurements NMR nlysis. All 1 H NMR spetr were reorded on Bruker AMX 300 t 300MHz in D 2. ize exlusion hromtogrphy. PAM nd P(AM-stt-AMP). EC ws rried out on Agilent 1100 HPLC system inluding vuum degsser nd n isorti pump monitored by n elipse 2 system (Wytt tehnonology), gurd olumn hodex B807-G nd three olumns hodex Hpk in series (two B-807 HQ (8mm*300mm, 35µm) nd one B-806M HQ (8mm*300 mm, 13µm)) oupled with refrtometer (ptilbrex, Wytt tehnology), UV detetor (Agilent) set t 290 nm nd multi-ngle lser light sttering detetor (Dwn HeleosII + QEL, 18 ngles, Wytt tehnology). The eluent used ws queous NN 3 0.1M with 100ppm NN 3. Prior to injetions, smples were diluted t onentrtion of 0.5 mg ml -1, stirred over week nd filtered through 0.45µm PTFE filters. Dn/d of eh smple ording to its omposition in AMP ws lulted with the Eq. 1 given below with dn/d (AM)=0.185 ml g -1 nd dn/d (AMP)=0.113 ml g -1 in the orresponding eluent t T=25 C. For the hin extension of PAM, olumn hodex B802.5 ws dded to the three previous desribed olumns. PDMA EC ws rried out on system omprising hodex KD-G gurd olumn nd two olumns K-805L (8mm*300mm, 5µm) oupled with refrtometer ( thermostted t 35 C (ptilb Rex, Wytt tehnology), UV detetor (Prostr, Vrin) set t 290 nm nd multi-ngle lser light sttering detetor (Mini Dwn, 3 ngles, Wytt tehnology). DMF/LiBr (10mM) ws used s eluent t 55 C with flow rte of 1 ml min -1.Prior to injetions, smples were diluted t onentrtion of 5 mg ml -1, stirred over week nd filtered through 0.45µm PTFE filters. Dn/d (PDMA)=0.087 ml g -1, dn/d (PNIPAM)=0.087 ml g -1 t 35 C in the orresponding eluent. Dn/d of blok opolymers ws lulted with Eq. 1 given below. P(NIPAM-blok-DMA) The system is the sme s for PDMA exept for the olumns: hodex KD-G gurd olumn nd three olumns hodex KD-804 (8mm*300mm, 7µm), KD (8mm*300mm, 6µm) nd K-805L (8mm*300mm, 5µm). P(DMA-stt-AMP). EC ws rried out on system omprising two olumns PL-qugel-mixed H-8µm (Agilent, 30 m) oupled with refrtometer (Agilent) nd multi-ngle lser light sttering detetor (Mini Dwn TRE, 3 ngles, Wytt tehnology). 15% methnol / 85% queous NCl 100 mm, NH 2 P 4 25 mm, N 2 HP 4 25 mm buffer solution (ph=7) ws used s eluent nd smples were injeted t 0.5 mg ml -1 nd filtered through 0.45 µm PTFE filters. Dn/d of eh smple ws lulted from Eq. 1 desribed below with dn/d (DMA)=0.160 ml g -1 nd dn/d (AMP)=0.133 ml g -1 in the orresponding eluent. Note: dn/d of P(A/B) opolymers ws lulted ording to the following eqution 1: dn/d (A/B) =W A *(dn/d) A +W B *(dn/d) B (Eq. 1) where W A nd W B re the mss frtion of monomers A nd B in the opolymer, respetively.
5 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 II. Mro-MADIX gents hrteriztion A. PAM 7 -XA1 7 H 2 N AIBN EtH:wter 60 C NH 2 heme 1: yntheti pthwy for the synthesis of PAM 7 -XA1 mro-madix gent e g h b 6 NH 2 NH 2 d f f e b + + g h d f1 (ppm) Figure 1 : 1 H NMR spetrum nd ssignements of signls for PAM 7 -XA1 in D DP = b
6 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 B. P(AM-stt-AMP) 7 -XA1 H 2 N + H 2 N 3 N + V-50 EtH:wter 60 C H 2 N stt n HN m 3 - N + heme 2: yntheti pthwy for the synthesis of hydrophili P(AM-stt-AMP) 7 -XA1 mro- MADIX gent d b H 2 N d' e stt n HN e' d f m i H 2 N g h i j 3 - N + b+d+e+i+h+d +e g f j f1 (ppm) Figure 2 : 1 H NMR spetrum nd ssignements of signls for P(AM-stt-AMP) 7 -XA1 in D 2 Mn = DP(AM) M(AM) + DP(AMP) M(AMP) + M(RHDiXAN) Mn = e M(AM) + j/2 M(AMP) + M(RHDiXAN)
7 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 C. PDMA 7 -XA1 7 N AIBN EtA 60 C N heme 3: yntheti pthwy for the synthesis of PDMA 7 -XA1 mro-madix gent Figure 3 : 1 H NMR spetrum nd ssignements of signls for PDMA 7 -XA1 in CDCl 3 DP lultion of PDMA 7 -XA1: DP = g 6m 6
8 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 III. Molr msses results A. Homopolymers Tble 1. Aqueous RAFT/MADIX polymeriztion of AM. [AM] 0 =4.65 mol L -1, [AP] 0 =[NF] 0 = mol L -1 (600ppm / AM monomer),t=10 C, t=2h, AM onv.=100% PAM homopolymers M n,theo/ M n,ec/ b M w,ec/ b Ð b reovery % Xnthte free M n,theo=([am] 0/[PAM 7-XA1] 0)*M AM*AM onv. + M(PAM 7-XA1), b determined by EC-RI-MAL in 0.1M NN 3/100ppm NN 3 with dn/d=0.185 ml g -1, reovery is the rtio of the mss tully eluted over the initil mss of the smple 7 1.0x10 Molr Mss vs. time M n,th = Xnthte free polym. M n,th = dri Molr Mss (g/mol) 6 1.0x time (min) Figure 4 : Log(molr mss)= f(time) for PAM homopolymers under the overly of hromtogrm
9 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 Tble 2. Aqueous RAFT/MADIX polymeriztion of DMA. [DMA] 0 =2 mol L -1, [AP] 0 =[NF] 0 = mol L -1 (1500 ppm / DMA monomer),t=20 C, t=2h, DMA onv.=100% PDMA homopolymers M n,theo/ M n,ec/ b M w,ec/ b Ð b reovery % Mn,theo=([DMA] 0/[PDMA 7-XA1] 0)*M DMA*DMA onv. +M(PDMA -XA1), b determined by EC-RI-MAL in DMF/LiBr (10 mm) with dn/d=0.087 ml g -1 Mn,th= Mn,th= Mn,th= Mn,th= Mn,th= retention time (min) Figure 5 verly of EC hromtogrms of PDMA synthesized t 20 C in wter using vrying onentrtions of PDMA 7 -XA1 B. AMP-bsed sttistil opolymers Tble 3. Aqueous RAFT/MADIX polymeriztion of AM nd AMP [AM] 0 =1.91 mol L -1,[AMP] 0 =0.64 mol L -1 [AP] 0 =[NF] 0 = mol L -1 (280 ppm / AM +AMP monomers),t=10 C, t=2h, AM nd AMP onv.=100% P(AM 75 -stt-amp 25 ) M n,theo/ M n,ec/ b M w,ec/ b Ð b reovery % Xnthte free M n,theo=(mam 0/n(P(AM-stt-AMP)) 7-XA1) 0+ mamp 0/n(P(AM-stt-AMP) 7-XA1) 0 + M(P(AM-stt-AMP) 7-XA1), b EC-RI-MAL in 0.1 M NN 3/100 ppm NN 3 with dn/d=0.147 ml g -1 determined by
10 Eletroni upplementry Mteril (EI) for Polymer Chemistry This journl is The Royl oiety of Chemistry 2014 Tble 4. Aqueous RAFT/MADIX polymeriztion of DMA nd AMP [AP] 0 =[NF] 0 = mol L -1 (1800 ppm / DMA +AMP monomers),t=20 C, t=2h, DMA nd AMP onv.=100% P(DMA-stt-PAMP) %AMP M n,ec/ b M w,ec/ b Ð b reovery % Mn th=1000k Xnthte free polym Mn th=1000k Xnthte free polym Mn th=1000k Xnthte free polym Mn th=1000k Xnthte free polym b Mn,theo=(mDMA 0/n(PDMA 7-XA1) 0+ mamp 0/n(PDMA 7-XA1) 0 + M(PDMA 7-XA1), determined by EC-RI-MAL in 15% methnol / 85% queous NCl 100mM, NH 2P 4 25mM, N 2HP 4 25mM with ponderted dnd for eh opolymer omposition by using dn/d (DMA)=0.160 ml g -1 nd dn/d (AMP)=0.133 ml g -1 9% AMP xnthte free polym. Mnth= % AMP xnthte free polym. Mnth= retention time min retention time min 33% AMP xnthte free polym. Mnth= % AMP xnthte free polym. Mnth= retention time min retention time min Figure 6 : verly of EC hromtogrms for P(DMA-stt-AMP) for eh AMP omposition for M n,th = nd xnthte free polymeriztion
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