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Ep 2616499 B1 (19) TZZ __T (11) EP 2 616 499 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C08G 73/18 (2006.01) 11.03.2015 Bulletin 2015/11 (86) International application number: (21) Application number: 11776596.6 PCT/IN2011/000628 (22) Date of filing: 14.09.2011 (87) International publication number: WO 2012/035556 (22.03.2012 Gazette 2012/12) (54) QUATERNISED POLYBENZIMIDAZOLE QUATERNISIERTES POLYBENZIMIDAZOL POLYBENZIMIDAZOLE QUATERNISÉ (84) Designated Contracting States: • BHAVSAR, Rupesh, Sudhakar AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Maharashtra (IN) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (74) Representative: Towler, Philip Dean Dehns (30) Priority: 14.09.2010 IN DE21712010 St Bride’s House 10 Salisbury Square (43) Date of publication of application: London 24.07.2013 Bulletin 2013/30 EC4Y 8JD (GB) (73) Proprietor: Council of Scientific & Industrial (56) References cited: Research CN-A- 101 392 060 New Delhi 110 001 (IN) • KUMBHARKAR S C ET AL: "N-substitution of (72) Inventors: polybenzimidazoles:Synthesis and evaluation of • KHARUL, Ulhas, Kanhaiyalal physical properties", EUROPEAN POLYMER Maharashtra (IN) JOURNAL, PERGAMON PRESS LTD. OXFORD, • KUMBHARKAR, Santosh, Chandrakant GB, vol.45, no. 12, 1 December 2009 (2009-12-01), Maharashtra (IN) pages3363-3371, XP026764834, ISSN: 0014-3057, DOI: 10.1016/J.EURPOLYMJ.2009.10.006 [retrieved on 2009-10-13] Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 616 499 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 616 499 B1 Description FIELD OF THE INVENTION 5 [0001] The present invention relates to polymeric forms of ionic liquids, PFILs, based on polybenzimidazole (PBI). [0002] More particularly, the present invention further relates to a process for the synthesis of such polymeric forms of ionic liquids useful for gas sorption and permeation and separation. BACKGROUND AND PRIOR ART OF THE INVENTION 10 [0003] Polymeric materials exhibiting high CO2 sorption are attractive materials for their applicability as sorbent and gas separation membrane materials. Polybenzimidazole (PBI) based polymeric forms of ionic liquids (PFILs) have (i) excellent CO 2 sorption characteristics (ii) improved solvent solubility than parent PBIs (needed for membrane preparation either in flat sheet form or hollow fiber form) and (iii) high enough thermal stability. PBI based polymeric forms of ionic 15 liquids (PFILs) are not known in the literature. These materials since are derived from thermally stable PBIs and thus have high thermal stability than their PIL counterparts derived from vinyl monomers known in the prior art, which are aliphatic in nature. [0004] US2002/0189444 claims a liquid ionic compound of formula given below 20 25 for separation of CO2 from natural gas. [0005] WO2006/026064 describes a polymer comprising a polymerized ionic liquid monomer selected from (a) imi- dazolium-based ionic liquids, consisting of 1-[2-(methacryloyloxy)ethyl]-3-butyl-imidazolium tetrafluoroborate ([MABI] [BF4]), 1-(p-vinylbenzyl)-3-butyl-imidazolium tetrafluoroborate ([VBBI][BF 4]), (b) ammonium-based ionic liquids, consist- ing of (p-vinylbenzyl)trimethyl ammonium tetrafluoroborate ([VBTMA][BF 4]), (p-vinylbenzyl)triethyl ammonium tetrafluor- 30 oborate([VBTEA][BF 4]), (p-vinylbenzyl)tributyl ammonium tetrafluoroborate ([VBTBA][BF 4]),and (p-vinylbenzyl)trimethyl ammonium trifluoromethane sulfonamide ([VBTMA] [Tf2N]), condensation polymerization ionic monomers consisting of bis(2-hydroxyethyl)dimethyl ammouiumtetrafluoroborate ([BHEDMA][BF 4]),2,2-bis(methylimidazolium methyl)-1,3-pro- panediol tetrafluoroborate ([BMIMP][BF4]), and 2,2-bis(butylimidazolium methyl)-1,3-propanediol tetrafluoroborate ([BBIMP][BF4]) for absorption of CO2 gas. 35 [0006] US4898917 discloses a unique process for the preparation of N-substituted polybenzimidazole polymers from unsubstituted polybenzimidazole polymers. According to the process of the invention unsubstituted polybenzimidazole polymer is first reacted with an alkali hydride to produce a polybenzimidazole anion in DMSO which is then reacted with a substituted or an unsubstituted alkyl, aryl or alkenyl methyl halide at a temperature of about 50-120 °C for 5-48 hours to produce an N-substituted alkyl, alkenyl or aryl polybenzimidazole polymer. The substituted polybenzimidazole polymer 40 produced by this process can be formed into membranes, films, resins or fibers. The polymers can be used in reverse osmosis, ultrafiltration, microfiltration, electrodialysis, ion exchange and affinity chromatography. It is further described that the composition of the R substituent depends upon the desired N-substituted polybenzimidazole end product. [0007] An article titled "Advances in CO2 capture technology-The U.S. Department of Energy’s Carbon Sequestration Program" by José D. Fiqueroa in INTERNATIONAL JOURNAL OF GREENHOUSE GAS CONTROL 2 (2008) 9 -20, 45 discusses the use of ionic liquid [hmim][Tf2N] for dissolution of CO2. The ionic liquid is shown to have good thermal stability allowing the recovery of CO2 without requiring it to cool. The article discusses the development in the use of PBI membranes in H2/CO2 selectivity. The article further mentions a supported liquid membrane that is CO2 selective and stable at temperatures exceeding 300 °C. The membrane consists of an advanced polymer substrate and an ionic liquid. It is observed that in these supported liquid membranes transport takes place through the liquid within the pores 50 rather than through a solid phase. This feature allows the membranes to take advantage of higher liquid phase diffusivities while maintaining the selectivity of the solution diffusion mechanism. [0008] US2006/0021502 discloses cross-linked, supported polybenzimidazole membrane prepared by reacting poly- benzimidazole (PBI) with the sulfone-containing crosslinking agent 3, 4- dichloro-tetrahydro-thiophene-1, 1-dioxide. The cross- linked polymer exhibits enhanced gas permeability to hydrogen, carbon dioxide, nitrogen, and methane as com- 55 pared to the unmodified analog, without significant loss of selectivity, at temperatures from about 20 degrees Celsius to about 400 degrees Celsius. The cross linking agent has the general formula, 2 EP 2 616 499 B1 5 wherein R1 and R2 are independently selected from alkyl having from 1 to 20 carbons, aryl having from 6 to 18 carbons, substituted aryl; wherein R1 and R2 are connected to form a ring structure having from 2 in 5 carbons; and wherein X and Z are independently selected from chloride, bromide, and iodide The cross linked polymer is given below, 10 15 20 [0009] When ionic liquids (ILs) are impregnated in the porous membranes, all the pores of the porous support should be filled by IL. Moreover, only IL fraction is useful for the effective separation of gases. [0010] In supported ionic liquid membranes (SILMs), liquid is held in the pores of the support via relatively weak capillary forces. When the transmembrane pressure differential is greater than those forces, the liquid will be pushed 25 through the support, destroying the membrane. As a result, the SILMs mentioned above were only tested at pressure differentials of 0.2 atm (Ref: J. Membr. Sci. 2004, 238, 57; Ind. Eng. Chem. Res. 2007, 46, 5397-5404). Further, Poly (RTIL) films are reported to be brittle to make mechanically stable membranes. [0011] Vinyl polymers suffer from more drawbacks such as: Vinyl containing monomers have limitations on structural architecture, they are porous and such porous polymers carry the threat of draining of liquid through the pores. As 30 exemplified in the literature, present PFILs based on vinyl monomers are brittle and need to be crosslinked to form the film for membrane based separations. [0012] Copolymers incorporating imidazole moiety such as polyether benzimidazoles, poly(arylene ether benzimida- zole)s, poly(imide amide benzimidazole), poly(aryl ether benzimidazoles) and hyper branched polybenzimidazoles are known in literature. However, no prior arts have explored PFIL containing ionic liquid component incorporated in the 35 imidazole polymer backbone itself, unlike vinyl polymers, which contain ionic liquid imidazole component in the side chain. [0013] Therefore, there exists a need for polymeric forms of ionic liquids, where, the ionic liquids can be incorporated in the polymeric back bone itself to enhance the structural strength of the polymer thereby enabling the polymer to withstand to any differential pressure and thus with enhanced performance. [0014] Therefore, the present invention aims at fulfilling the existing need for polymeric forms of imidazoles or benz- 40 imidazoles where the ionic liquid moiety is present in the backbone of the polymer chain and exhibit a high degree of sorption for gases like CO2 at differential pressure. There also exists a need to provide a process of making PFIL that allows structural modification, which also the present invention aims to fulfill in the current invention. [0015] Another unfulfilled need in the literature is the ability of the PFILs to possess film forming characteristics without further modification
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