A Water-Soluble Polyimide Precursor: Synthesis and Characterization of Poly(amic acid) Salt
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1 Maromoleular Researh, Vol. 12, No. 3, pp (2004) A Water-Soluble Polyimide Preursor: Synthesis and Charaterization of Poly(ami aid) Salt Jun Yang and Myong-Hoon Lee* Department of Polymer Siene & Tehnology, Chonbuk National University, Dukjin, Dukjin, Chonju, Chonbuk Korea Reeived November 26, 2003; Revised Marh 22, 2004 Abstrat: We have synthesized a water-soluble polyimide preursor, poly(ami aid) amine salt (PAD), from pyromelliti dianhydride (PMDA), 4,4'-oxydianiline, and N,N'-dimethylethanolamine (DMEA) and have investigated in detail its properties with respet to the degree of salt formation (D sf ). The maximum value of D sf we obtained upon preipitation of the preursor solution into aetone was 79%. We synthesized a PAD having a D sf of 100% (PAD100) by the solid state drying of an organi solution. The preursors showed different solubility depending on the D sf to make up to 4 wt% solutions in water ontaining a small amount of DMEA. PAD100 is ompletely soluble in pure water. We investigated the imidization behavior of PAD in aqueous solution using various spetrosopi methods, whih revealed that PAD100 has faster imidization kinetis relative to that of the poly(ami aid)-type preursors. The resulting polyimide films prepared from an aqueous preursor solution possess almost similar physial and thermal properties as those prepared from N-methyl-2-pyrrolidone(NMP) solution. Therefore, we have demonstrated that PAD an be used as a water-based preursor of polyimide; this proedure avoids the use of toxi organi solvents, suh as NMP. Keywords: polyimide preursor, poly(ami aid) salt, PMDA, ODA, FTIR spetrosopy, water-soluble, stepwise thermal imidization. Introdution Polyimides (PI), a lass of high-performane materials, have been widely used as eletrial insulators, oatings, adhesives, substrates for flexible printed iruits, and alignment films for liquid rystal displays due to their high temperature stability, exellent mehanial properties and good hemial resistane. Conventionally PI were prepared in two steps: First, aromati dianhydride is added to a solution of aromati diamine in a highly polar aproti solvent suh as dimethylformamide (DMF), dimethylaetamide (DMA), dimethyl sulfoxide (DMSO), or N-methyl-2-pyrrolidone (NMP), until a highly visous poly(ami aid) (PAA) solution was obtained. Seond, poly(ami aid) is onverted to polyimide by either thermal or hemial imidization. Sine poly (ami aid)s are soluble only in strongly polar solvents as mentioned above, whih are toxi, areful handling is neessary to avoid environmental problems. Moreover, due to the hydrolyti instability for PAAs over storage, there have been efforts to prepare other preursors of polyimides, suh as * mhlee2@honbuk.a.kr /04/ Polymer Soiety of Korea poly(ami aid) esters, 1-2 and poly(ami aid) salts (PAAS), 3-6 whih have no storage problem in solution. Espeially, ompared to poly(ami aid) and poly(ami aid) ester, PAAS is attrative beause it is easy to synthesize and is soluble in water, whih are benefiial for both the environmental and pratial issues. Despite suh advantages, however, PAAS has not been studied systematially as a water-soluble preursor. In this paper, we desribed the synthesis and haraterization of water soluble polyimide preursor, poly(ami aid) dimethylethanol amine salt (PAD). In addition, its properties and imidization behavior were also investigated. Experimental Materials. Pyromelliti dianhydride (PMDA) and 4,4'- oxydianiline (ODA) were purhased from Aldrih and used after areful vauum sublimation. NMP was dried with alium hydride and vauum distilled before use. The saltforming ompound, N,N'-dimethylethanolamine (DMEA) (99 %) (Janssen Chimia), was used as reeived without further purifiation. Preparation of poly(ami aid)s (PAA). Poly(ami aid)s 263
2 J. Yang and M.-H. Lee (PAA) was prepared aording to the typial proedure 7 in a round-bottom flask under nitrogen atmosphere. PMDA (0.015 mole) was added to 55 ml of dry NMP solution ontaining dissolved stoihiometri equivalent amount of ODA (0.015 mole). The mixture was stirred for 18 hrs at room temperature. With the gradual dissolution of PMDA, visous and yellowish PAA solution was obtained. For NMR measurements, PAA powder was obtained by preipitating the reation mixture into aetone followed by subsequent drying at 40 o C in vauum oven overnight. Preparation of poly(ami aid) dimethylethanol amine salts (PAD) with different degree of salt formation (D sf ). PADs with various degree of salt formation (D sf ) were synthesized by adding different amount of DMEA (2.0, 1.5, 1.0, and 0.5 mole equivalent to PMDA, respetively) into the PAA solution. Typially, alulated amount of DMEA was added into PAA solution 8 at room temperature and the mixture was stirred for 45 min under nitrogen atmosphere. Upon the addition of DMEA, large inrease of visosity was observed with a loal white preipitation of polymer as reported by Kreuz et. al. 5 The preipitated polymer was redissolved in NMP with stirring to give homogeneous and yellowish solution. The solution was poured into aetone, and the preipitated solid was filtered, dried in vauum and pulverized in a mortar. Subsequent drying in vauum at 40 o C for 24 hrs gave light yellow PAD powder. It should be noted that the highest D sf ahieved by preipitation was a. 79%. PAD of 100% D sf (PAD100) was prepared by asting 4 wt% PAD solution (D sf = 79%) in 2% (v/v) DMEA/H 2 O on a glass plate and dried at 40 o C in vauum overnight. The omplete elimination of free amine was onfirmed by NMR spetrum in DMSO-d 6. Preparation of polyimide films. In this study, polyimide films were prepared by asting aqueous PAD100 solutions (4.0 wt.%) onto a glass plate followed by multi-step thermal imidization proesses as depited in Figure 2. A polyimide film was also obtained from PAA for omparison. In this ase, PAA solution in NMP was used with the same proedure. The thikness of the final films was a µm. Determination of degree of salt formation (D sf ). D sf was determined by 1 H-NMR (in DMSO-d 6, JEOL-EX, 400 MHz). In the 1 H-NMR method, the integration value of methylene proton peak of DMEA entered at 3.7 ppm was ompared to that of ODA aromati proton at 7.0 ppm. The detailed alulation is disussed in the results and disussion setion. Visosity Measurements. Inherent solution visosities (η inh ) were measured for 0.14% (v/v) dilute aqueous solution of PAD100. To investigate the hydrolyti stability, two aqueous PAD solutions of different onentrations, 0.14 and 3.5% (v/v), were stored at 25 o C, and visosity of the solution was measured periodially. It should be noted here that the 3.5% PAD100 aqueous solution was diluted to 0.14% solution before the visosity test. All the tests were performed by using Cannon-Fenske type visometers with apillaries sized to give flow rate in the se range in water bath with temperature ontrolled at o C. Thermogravimetri Analysis. Dynami thermal behavior of the polyimide films made from aqueous PAD100 solution and PAA solution in NMP were determined by measuring the weight losses while heating from 50 o C to 700 o C at 15 o C/min under nitrogen with gas flow rate of 40 ml/s by using thermogravimetri analyzer (TGA 2050, TA Instruments). FT-IR Measurement. Infrared spetra were obtained with Figure 1. Reation sheme for preparation of PAD from poly(ami aid) in NMP. Figure 2. Stepwise thermal imidization proedure (Vauum + Furnae). 264 Maromol. Res., Vol. 12, No. 3, 2004
3 A Water-Soluble Polyimide Preursor: Synthesis and Charaterization of Poly(ami aid) Salt JASCO Model 300E FT-IR spetrometer at a resolution of 2m -1 and 30 aumulations in order to study the stepwise uring temperature effet on the degree of imidization. Thin films were made by spin-oating 4% (g/ml) PAD100 aqueous solution and 5% (g/ml) in DMSO solution, respetively, onto small squared silion wafers followed by a subsequent drying at room temperature in vauum oven overnight. PAA film was also made in the same way from 10% (g/ml) NMP solution for omparison. The absene of solvent in the film before thermal uring was onfirmed from the FT-IR spetra (Figure 7) in order to eliminate the solvent effet on the thermal imidization. 9,10 Results and Disussion Determination of D sf. Degree of salt formation is alulated from 1 H-NMR spetrum (JEOL-EX 1 H-NMR spetrometer, 400 MHz). In Figure 3, 1 H-NMR spetrum of PAD salt was ompared with those of free PAA and DMEA. H e and H f peaks shifted downfield due to the formation of ammonium salt. D sf was obtained by omparing the integral values of H e with that of H a by the following equation: D sf ( %) 2m = = 4 A ---- e A a where, 2m and 4 denote the numbers of proton e and a, respetively, in one PAD moleule unit and A is the area under the orresponding peaks. Syntheses of PADs. To investigate the effet of reation ondition on the salt formation degree (D sf ), the mole ratio of PAA and DMEA was varied from 1.0 : 0.5 to 1.0 : 4.0 (PAA : DMEA). The results were summarized in Table I. In the ase of PADs prepared by preipitation, the highest D sf of a. 79% was obtained when the stoihiometri amount of Figure 3. 1 H-NMR spetra of N,N-dimethylethanolamine (DMEA), free poly(ami aid) (PAA), and its orresponding ammonium salt (PAD). (1) Table I. Effets of PAA:DMEA Mole Ratio and Reation Time on D sf of PAD Sample Number PAA:DMEA (Mole ratio) a Reation time (hr) D sf (mole %) b Dissolve time (min.) in DMEA/H 2 O PAD-1 1: PAD-2 1: PAD-3 1: PAD-4 1: PAD-5 1: PAD-6 1: PAD-7 1: PAD-8 1: PAD-9 1: PAD-10 1: a Per one repeating unit of PAA. b D sf values are estimated from NMR spetra. 2.0 % (v/v) DMEA in DMEA/H 2 O mixed solvent. DMEA was used to the PAA repeating unit. Larger amounts of DMEA did not have signifiant effet on the inrease of salt formation degree (D sf ). In this experiment, PADs from PAD-1 to PAD-4 were used for further haraterizations. In addition to these, the reation time was varied, and the results are also shown in Table I. Reation time did not affet the salt formation degree onsiderably. The low salt formation degree would be attributed to the elimination of amine moleules due to the equilibrium hange between free amine and ammonium salt during the preipitation into aetone. The resulting polymers were insoluble in pure water, but soluble in 2% (v/v) DMEA/H 2 O mixture to make a homogeneous solution of up to 4 wt% solid ontent. The higher D sf, the faster dissolution was observed in DMEA/H 2 O mixed solvent. When the above PAD samples (PAD-1 ~ PAD-4) were redissolved in 2% (v/v) DMEA/H 2 O mixture, ast on a glass plate, and dried at 40 o C in vauum for overnight, PADs of 100% D sf (PAD100) were obtained. From the NMR spetra of PAD100 in DMSO-d 6, 100% salt formation degree was onfirmed by the absene of peaks orresponding to free amine and exat agreement in integration values of other peaks. Therefore, it is not likely that the elimination of free amine ourred during the vauum drying in the ase of PAD-1~PAD-4. The resulting polymer was soluble in pure water as well as in DMSO, while the PADs (PAD-1~PAD- 4) obtained from the preipitation method were only soluble in water ontaining extra DMEA. Hydrolyti stability of PAD100 in aqueous solution. In Figure 4, hanges of the intrinsi visosity of 0.14% (v/v) and 3.5% (v/v) aqueous PAD100 solutions stored at 25 o C were plotted against the storage time. Compared to the PAA in DMA, whih exhibits a fast derease in visosity due to Maromol. Res., Vol. 12, No. 3,
4 J. Yang and M.-H. Lee Figure 4. Effet of onentration and storage time on the stability of PAD100 in aqueous solution. the aid-atalyzed hydrolysis as reported by Sroog et al., 7 aqueous PAD solutions showed muh slower derease in visosity for both ases. The more onentrated solution of 3.5% (v/v) PAD exhibited even better stability than the diluted solution. The improved stability of PAD may be attributed to that the aid-atalyzed hydrolysis to amine and unstable anhydride is suppressed by the presene of amine salts. 17 FT-IR Experiment. Thermal imidization of the ast films was performed by stepwise heating for overnight at room temperature, 2 hrs at 40 o C, 2hrs at 80 o C, 1 hr at 160 o C under vauum ondition, and then 30 min eah at 250, 300, and 350 o C 11 in the furnae. To avoid possible water sorption, 12 the sample films were ooled in the furnae to 50 o C after eah heating steps, and the FT-IR measurement was done as quikly as possible. The infrared spetra of polymer films obtained from aqueous PAD100 solution, PAD100 solution in DMSO and PAA solution in NMP were ompared during the stepwise thermal imidization. As seen in Figure 5(a), for the film made from aqueous PAD100 solution, the adsorption at 1550 m -1 (amide I: C(=O)NH vibration) disappeared and the absorption peak at 1380 m -1 orresponding to imide C-N strething vibration 13 appeared after 80 o C. In omparison, for the film prepared from NMP solution of PAA, suh phenomenon ould only be observed after uring at 160 o C. This implies that PAD100 in aqueous solution starts to be imidized at 80 o C, whih is muh lower temperature than that of PAA in NMP. The band appearing at 1500 m -1 (C-C strething of the p- substituted benzene) was used as an internal standard for the alibration purpose. 13 Among the bands indiative of the imide formation during the uring, the band at 1380 m -1 (imide II: C-N strething vibration), was used as the measure of imidization onversion perent sine the two imide feature bands at 1720 and 1780 m -1 fell in the region of anhydride Figure 5. Effet of uring temperature on the FT-IR spetra of (a) PAD100 film made from PAD100 aqueous solution, and (b) PAA film from PAA (PMDA/ODA) in NMP solution. absorption. 14 The onversion (%) to polyimide was alulated by the following equation 15 : ( D 1 Conversion to PI (% ) 1380m D m ) = T 100 ( D m D m ) 350 o C (2) where D is the optial density. Figure 6 summarizes the onversion (%) to polyimide at various uring temperatures for the films of from aqueous PAD100 solution (Figure 6a), from PAD100 in DMSO solution (Figure 6b), and from PAA in NMP solution (Figure 6). Both films prepared from PAD100 solutions in water and DMSO showed more than 95% imidization at 160 o C under vauum ondition, while the film from PAA solution in NMP showed only 50% onversion. Furthermore, 50% of imidization was deteted at 80 o C for the film from aqueous PAD100 solution, while almost no imidization was observed in either ase of PAD100 in DMSO and PAA in NMP. Imidization degrees between 160 o C and 266 Maromol. Res., Vol. 12, No. 3, 2004
5 A Water-Soluble Polyimide Preursor: Synthesis and Charaterization of Poly(ami aid) Salt Figure 6. Conversion to PI (%) at various uring temperatures for (a) PAD100 in water, (b) PAD100 in DMSO, and () PAA in NMP. Figure 8. FT-IR spetra of PI films made from (a) PAD100 aqueous solution, and (b) PAA (PMDA/ODA) in NMP solution. Figure 9. TGA of PI films from poly(ami aid) in NMP solution (solid line), and PAD100 aqueous solution (dashed line). Figure 7. Different solvent effet on the IR spetra of (a) PAD100 film from 4.0% (v/v) PAD100 aqueous solution, (b) PAD100 film from 5.0% (v/v) PAD100 in DMSO solution, and () film from PAA solution in NMP. All are treated at 40 o C for 2hrs under vauum ondition before test. 250 o C for PAD100 films were also muh higher than PAA film, whih an be attributed to the different hemial strutures of preursors. For the film from the aqueous PAD100 solution (Figure 7a), the harateristi band of COOH at 1720 m -1 disappeared, and a band at 1580 m -1 whih is harateristi of arboxylate arbonyls appeared. This suggests all the arboxyli aid groups in PAD100 have been onverted into arboxylate anions due to the ionization effet in water. In other ases (Figure 7b and 7), however, the arboxyli aid group is still present. This suggests the formation of the arboxylate anion as the preferred preursor to the ativated omplex is important for the imide ring losure. 16 Thermal stability. The hemial strutures of the final polyimide films obtained either from onventional PAA-NMP or PAD100 aqueous solution after the same thermal imidization proedure were almost idential as onfirmed by FT-IR spetra shown in Figure 8. Thermal stability has been determined for both polyimide films by weight loss measurement. The results of thermal properties and physial properties, summarized in Figure 9 and Table II, show the polyimide film made from aqueous PAD100 solution still retains relatively high thermal stability, good hardness and toughness. There were slight losses of thermal stability and transpareny ompared with those of PI film obtained from onventional poly(ami aid). It is proposed that the small derease of Maromol. Res., Vol. 12, No. 3,
6 J. Yang and M.-H. Lee Table II. Thermal and Physial Properties of final Polyimide Films Sample Number moleular weight has ourred due to the presene of free DMEA whih ated as a base atalyst for the deomposition of amide linkages during the uring proess. This interpretation an explain the differene of thermal stability between the two polyimide films. Conlusions T i (ºC) T d1 (ºC) T d2 (ºC) Residue at 700 ºC (%) Penil Hardness 1 a HB~H 2 b HB~H a Polyimide film prepared from PAA(PMDA/ODA) in NMP solution. b Polyimide film prepared from aqueous PAD100 solution. T i, T d1, and T d2 are the initial deomposing temperature, 1% weight loss temperature, and 5% weight loss temperature, respetively. We reported the preparation of water-soluble poly(ami aid) salt (PAD) as a preursor for polyimide. In order to study the solubility of PAD in water, PAD samples with different amine frations were prepared from the reation of the orresponding free poly(ami aid) and dimethyl ethanol amine. The inrease of the ion onentration in water was suggested to interpret the solubility inrease of PAD with higher amine moiety. PAD having 100% degree of salt formation (PAD100) showed omplete dissolution in pure water, whih an be used as an aqueous preursor solution for making a polyimide film. The imidization behavior of the resulting PAD100 aqueous solution was first investigated by using FT-IR spetrosopy. The polyimide film prepared from aqueous PAD100 solution showed faster imidization kinetis ompared to that made from PAA solution in NMP, whih was explained by the presene of arboxylate anion ating as a preferred intermediate for the imide ring losure. The resulting polyimide film showed almost omparable physial and thermal properties as those of onventional polyimide prepared from NMP solution. In onlusion, we showed that PAD an be used as an water-based preursor of polyimide, whih onsequently an avoid the use of toxi organi solvents suh as NMP. Aknowledgements. This work was supported by Korea Researh Foundation Grant (KRF E00335). Referenes (1) N. Yoda and H, Hiramoto, J. Maromol. Si. Chem., A21, 1641 (1984). (2) S. Kubota, T. Moriwaki, T. Ando, and A. Fukami, J. Appl. Polym. Si., 33, 1763 (1987). (3) Q. Li, T. Yamashita, K. Horie, H. Yoshimoto, T. Miwa, Y. Maekawa, J. Polym. S., Part A: Polym. Chem., 36, 1329 (1998). (4) Y. Ding, B. Bikson, and J. K. Nelson, Maromoleules, 35, 905 (2002). (5) J. A. Kreuz, A. L. Endrey, F. P. Gay, and C. E. Sroog, J. Polym. Si., Part A: Polym. Chem., 4, 2607 (1966). (6) R. J. W. Reynolds and J. D. Seddon, J. Polym. Si., Part C: Polym. Lett., 23, 45 (1968). (7) C. E. Sroog, A. L. Endrey, S. V. Abramo, C. E. Berr, W. M. Edward, and K. L. Olivier, J. Polym. Si., Part A: Polym. Chem., 3, 1373 (1965). (8) A. L. Endrey, U. S. Pat. 3,179,631 (1965). (9) I. Kardash, A. Y. Ardashnikov, F. S. Yakushin, and A. N. Pravednikov, Polym. Si. USSR, 17, 689 (1975). (10) N. C. Stoffel, E. J. Krame, W. Volksen, and T. P. Russell, Polymer, 34, 4524 (1993). (11) J. V. Fainelli, S. L. Gardner, L. Dong, C. L. Sensenih, R. M. Davis, and J. S. Riffle, Maromoleules, 29, 7342 (1996). (12) K. H. Yu, Y. H. Yoo, J. M. Rhee, M.-H. Lee, and S.-C. Yu, Mat. Res. Innov., 7, 51 (2003). (13) H. Han, C. C. Gryte, and M. Ree, Polymer, 36, 1663 (1995). (14) C. A. Pryde, J. Polym. Si., Part A: Polym. Chem., 27, 711 (1989). (15) S. Gan, J. Si. Eng. Comp. Mater., 2, 119 (1992). (16) K. Kim, S. Choi, S. Kim, S. Chao, and C. Wang, J. Mat. Si., 28, 1537 (1993) (17) T. Nishino, M. Kotera, N. Inayoshi, N. Miki, and K. Nakamae, Polymer, 41, 6913 (2000). 268 Maromol. Res., Vol. 12, No. 3, 2004
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