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I I W O 2U12/U35556 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date i i 22 March 2012 (22.03.2012) W O 2U12/U35556 Al (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C08G 73/18 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/IN20 11/000628 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 14 September 201 1 (14.09.201 1) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, (26) Publication Langi English RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW. 2171/DEL/2010 14 September 2010 (14.09.2010) IN (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): COUN¬ kind of regional protection available): ARIPO (BW, GH, CIL OF SCIENTIFIC & INDUSTRIAL RESEARCH GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, [IN/IN]; Anusandhan Bhawan, Rafi Marg, New Delhi 110 ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, 001 (IN). TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors; and LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, (75) Inventors/ Applicants (for US only): KHARUL, Ulhas, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Kanhaiyalal [IN/IN]; National Chemical Laboratory, Dr. GW, ML, MR, NE, SN, TD, TG). Homi Bhabha Road, Pune 4 11 008, Maharashtra (IN). KUMBHARKAR, Santosh, Chandrakant [IN/IN]; N a Declarations under Rule 4.17 : tional Chemical Laboratory, Dr. Homi Bhabha Road, — as to applicant's entitlement to apply for and be granted Pune 4 11 008, Maharashtra (IN). BHAVSAR, Rupesh, a patent (Rule 4.1 7(H)) Sudhakar [IN/IN]; National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 4 11 008, Maharashtra (IN). — of inventorship (Rule 4.1 7(iv)) SHEVATE, Rahul, Hanumant [IN/IN]; National Chem Published: ical Laboratory, Dr. Homi Bhabha Road, Pune 4 11 008, Maharashtra (IN). — with international search report (Art. 21(3)) (74) Agent: SALHOTRA, Anuradha; Lall Lahiri & Salhotra, — before the expiration of the time limit for amending the Plot No. B-28, Sector 32, Institutional Area, Gurgaon 122 claims and to be republished in the event of receipt of 001, Haryana (IN). amendments (Rule 48.2(h)) * * © © (54) Title: QUATERNISED POLYBENZIMIDAZOLE (57) Abstract: The invention discloses polymeric forms of ionic liquids, PFILs, based on polybenzimidazole (PBI) and a process ¾ for the synthesis of such polymeric forms of ionic liquids. The invention also relates to use of PBI based polymeric forms of ionic liquids and their membranes for gas sorption, permeation and separation. QUATERNISED POLYBENZIMIDAZOLE FIELD OF THE INVENTION The present invention relates to polymeric forms of ionic liquids, PFILs, based on polybenzimidazole (PBI). 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 Polymeric materials exhibiting high C0 2 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 C0 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 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. US2002/0 189444 claims a liquid ionic compound of formula given below for separation of C0 2 from natural gas. WO2006/026064 describes a polymer comprising a polymerized ionic liquid monomer selected from (a) imidazolium-based ionic liquids, consisting of l-[2-(methacryloyloxy)ethyl]-3- butyl- imidazolium tetrafluoroborate ([MABI] [BF4]), 1 -(p-vinylbenzyl)-3-butyl-imidazolium tetrafluoroborate ([VBBI][BF 4]), (b) ammonium-based ionic liquids, consisting of (p- vinylbenzyl)trimethyl ammonium tetrafluoroborate ([VBTMA] [BF4]), (p-vinylbenzyl)triethyl ammonium tetrafluoroborate ([VBTEA][BF4]), (p-vinylbenzyl)tributyl ammonium tetrafluoroborate ([VBTBA][BF4]), and (p-vinylbenzyl)trimethyl ammonium tnfluoromethane sulfonamide ([VBTMA] [Tf2N]), condensation polymerization ionic monomers consisting of bis(2- hydroxyethyl)dimethyl ammouium tetrafluoroborate ([BHEDMA][BF4]), 2,2- bis(methylimidazolium methyl)- 1,3 -propanediol tetrafluoroborate ([BMIMP][BF4]), and 2,2- bis(butylimidazolium methyl)- 1,3-propanediol tetrafluoroborate ([BBIMP][BF4])for absorption ofC0 2 gas. 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 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. An article titled "Advances in C0 2 capture technology—The U.S. Department of Energy's Carbon Sequestration Program" by Jose D. Fiqueroa in INTERNATIONAL JOURNAL OF GREENHOUSE GAS CONTROL 2 (2008) 9 -20, discusses the use of ionic liquid [hmim][Tf2N] for dissolution of C0 2. The ionic liquid is shown to have good thermal stability allowing the recovery of C0 2 without requiring it to cool. The article discusses the development in the use of PBI membranes in H2/C0 2 selectivity. The article further mentions a supported liquid membrane that is C0 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 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. US2006/0021502 discloses cross-linked, supported polybenzimidazole membrane prepared by reacting polybenzimidazole (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 compared 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, o X— R—S— R2— o wherein R and R are independently selected from alkyl having from 1 to 20 carbons, aryl having from 6 to 18 carbons, substituted aryl; wherein R and R 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, 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. 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 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. 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 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. Copolymers incorporating imidazole moiety such as polyether benzimidazoles, poly(arylene ether benzimidazole)s, poly(imide amide benzimidazole), poly(aryl ether benzimidazoles) and hyper branched polybenzimidazoles are known in literature. However, no prior arts have explored
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