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1 DOI: /jcprm , ( ). 1*,. 1,. 2 1,, 37,, ( ), zj@weburg.me, gvictor@e1.ru 2,, 21,,, ( ), o.shishlov@ucp.ru, -,, (Cashew Nut Shell Liquid).,.,.. :,,,,,,.,,. -., -,, - [1]., - [2]. [3 5], - Cashew Nut Shell Liquid (, CNSL).,, (C15). [3 5],,,.: (343) , gvictor@e1.ru, zj@weburg.me,.: (3435) , shishlov@ucp.ru [5]. -, -,. *,.
2 6.,.,. : Anacardium occidentale L,, -. [4, 5], (N-CNSL) -, (I), (II), (III) 2- (IV): OH COOH OH OH H 3 C OH R R HO R HO I II III IV R, R,,,. (D-CNSL DD-CNSL),., : -,,,. 1. C.K.S. Pillai [6 8]. -,, -,,, -.,,,.. [6] -. (GP ). -., 20 (0,67 ),. 180 C.,, - (0,2, 1%) ( ), ( 4 10 ) - ( 0 3%)., 140 1%., % %,., C C, C. 1,2 30 C 3,4 140 C.
3 , 7 2% - (. 1). -. : 6, C 8, C. 8,98. [6],.. -., -, : C.K.S. Pillai G. John [7, 8] -. S. Manjula, V.G. Kumar,.S. Pillai [9] -, ( H 2 SO 4 ) ( H 3 PO 4 ). H 2 SO 4 25%- ( ). 50 (0,166 ) 3 ( 0,014 0,017 ), C 30..,., H 3 PO , -,, 600, , -. (. 2), GPC, ,. 1. [4] a BF 3 OEt 2, %, %, % % M n M w D b 0, ,88 0, ,83 1,0 12,6 12,6 74, ,06 2, ,15 3,0 c a 140 C 10 ; b D = M w /M n = ; c.
4 8.,.,. 2. [9], %., C, , ,009 3 H 2 SO 4 (6%) ,032 4 H 3 PO 4 (10%) , [9], (M), % (DM), % (T), % (TM), % 1 100,0 2 94,13 2,68 3,19 3 9,90 9,30 21,41 59, ,07 35,50 17,11 26,30 GPC, - 1 [9] - (V):, -,. ( ), -. (D), (T) -. [9],,, - : DES H 2 SO 4 50 C [9]. [10],. 5%
5 , 9 2. S. Kobayashi. - : [1, 2]. -,. [1], - : - ( );, ;. - [2]. ( ) ),,, (. 4). ( 4. 4). 0,60 (2,0 ) 20 12,5 12,5 (ph 7) (6%-, 1,5, 2,0 ) (20 ),.. -.,,, 0,41 (69%)., -,. (M n ) (M n /M w ) -. (. 4),,, a -, -, ), % M n M n / M w, % 1 5 / (20) ,7 19 (75 : 25) 2 5 / (20) (75 : 25) 3 5 1,4- / - (20) (85 : 15) 4 2 / - (10) ,8 0 (50 : 50) 5 2 / - (50) (50 : 50) 6 2 / - (10) (70 : 30) 7 2 / (50 : 50) (10) ,6 35 a (0,6 ) (25 ) -.
6 10.,.,. 1 - [2], -, -, - : R (3 %) (34 %) (22 %) (41 %),, [2]. [11] (3- ). H 2 O 2-24., (72 85%) ph.. 3-, %. -, -. - [12] C.,. [1] (83 84%) Fe-Salen (Fe, Co, Cu.) Salen,. Fe-Salen Fe-N,N'- ).. (6,0, 20 ) Fe-Salen (64, 0,20 ). (30%-, 2,3, 20 ) Fe-Salen 0,5 1,5% ( ),., 0,5%,, 1,0 1,5%., 30,, 2. -
7 , %, , (M w /M n ) 1,6 4, C -.,, Fe-Salen,. - Salen,, Salen -. 1, -., II,, III IV, -.,, : (3% ) ( C 30 ). ( 23 41%). -,,,. -.,. 3. Q. Chen, H. Xue, J. Lin [13] -. -,, -. ( ) - 2,1 6 /10. - ( ).. : -, /. 180 C 50./. -,. 80 C , 0,2% (d ) ( -g- ), [13] -.,, -,,, :
8 12.,.,.. ( ) -,. ( ) g-, -,,. -g- -. -g-, - ( -g- ) 5., 20% -g-, 20. -g g-, [13],,, %, % 1005±24 54,5±0,30 41±2 48,2 -g- 808±28 45,1±0,98 846±23 47,2 1498±55 31,43±1,07 16±1 24,79 -g- 1226±51 31,49±1,49 37±1 24, , -,.,,.
9 , Ikeda R., Tanaka H., Uyama H., Kobayashi S. Synthesis and curing behaviors of a crosslinkable polymer from cashew nut shell liquid // Polymer Vol. 43, N12. Pp Ikeda R., Tanaka H., Uyama H., Kobayashi S. Enzymatic-synthesis and curing of poly(cardanol) // Polymer J Vol. 32, N7. Pp Manjula S., Pillai C.K.S. Naturally Occurring Organic Bio-Monomers as Possible Future Sourses for Polymers // Polymer News Vol. 12, N12. Pp Talbiersky J., Polaczek J., Ramamoorty R., Shishlov O. Phenols from Cashew Nut Shell Oil as a Feedstock for Making Resins and Chemicals // OIL GAS Europeen Magazine N1. p ,., - ( ) // Antony R., Pillai.S. GPC Studies on The Cationic Polymerization of Cardanol Initiated by Borontrifluoridediethyletherate // J. Appl. Polym. Sci Vol. 41. N7 8. Pp John G., Pillai C.K.S. Grafting of bio-monomers. 1. Cationic graft copolymerisation of cardanol using borontrifluoridediethyletherate onto cellulose // Polym. Bull Vol. 22, N1. Pp John G., Pillai C.K.S. Chemical modification of cellulose by cationic grafting of vinyl biomonomers: Structure and properties // 33rd IUPAC Int. Symp. Macromol., Montreal, July 8 13, 1990: Book Abstr. [Montreal] P Manjula S., Kumar V.G., Pillai.S. Kinetics and Mechanism of Oligomerization of Cardanol Using Acid Catalysts // J. Appl. Polym. Sci Vol. 45. N2. Pp Patent (KR). Preparation method of cardanol polymer / Choi Jeong Su, Park Jae Yeon Alva K.Sh., Nayak P.L., Kumor J., Tripanthy S.K. Enzymatic polymerization of phenolic biomonomers derived from Cashew nut shell liquid // J. Macromol. Sci. A Vol. 34. N4. p Kim Y.H., Won K., Kwon J.M., Jeong H.S., Park S.Y., An E.S., Song B.K. Synthesis of polycardanol from a renewable resource using a fungal peroxidase from Coprinus cinereus // J. Mol. Catal. B Vol. 34. N1 6. Pp Chen Q., Xue H., Lin J. Preparation of Polypropylene-graft-Cardanol by Reactive Extrusion and Its Composite Material with Bamboo Powder // J. Appl. Polym. Sci Vol. 115, N2. Pp Glukhikh V.V. 1*, Shkuro A.E. 1, Shishlov O.F. 2 SYNTHESIS, PROPERTIES & APPLICATIONS POLYMERIZATION PRODUCTS OF CARDANOL (REVIEW) 1 Ural State Forest Engineering University, Sibirskii trakt, 37, Ekaterinburg, (Russia), zj@weburg.m, gvictor@e1.ru 2 Uralchimplast, Severnoye shosse, 21, Nizhny Tagil, Sverdlovsk region, (Russia), o.shishlov@ucp.ru Synthesis, properties and applications of polymerization and copolymerization products of ardanol which is natural phenol derived from plant materials (Cashew Nut Shell Liquid) were considered. The results of studies of ardanol polymerization in the presence of radical type initiators, cation initiators, enzymes and metal complexes were described. This paper shows that cationic and radical types of catalysts lead to ardanol polymerization by opening the double bonds in alkyl substituent. In case of the oxidative polymerization growth of ardanol polymer chain occurs with the participation of double bonds in the phenolic ring. Keywords: review, cardanol, polymerization, copolymerization, products, properties, applications. * Corresponding author.
10 14.,.,. References 1. Ikeda R., Tanaka H., Uyama H., Kobayashi S. Polymer, 2002, vol. 43, no. 12, pp Ikeda R., Tanaka H., Uyama H., Kobayashi S. Polymer J., 2000, vol. 32, no. 7, pp Manjula S., Pillai C.K.S. Polymer News, 1987, vol. 12, no. 12, pp Talbiersky J., Polaczek J., Ramamoorty R., Shishlov O. OIL GAS Europeen Magazine, 2009, no. 1, pp Shishlov O.F., Glukhikh V.V. Khimiia rastitel'nogo syr'ia, 2011, no. 1, pp (in Russ.). 6. Antony R., Pillai.S. J. Appl. Polym. Sci., 1990, vol. 41, no. 7 8, pp John G., Pillai C.K.S. Polym. Bull., 1989, vol. 22, no. 1, pp John G., Pillai C.K.S. 33rd IUPAC Int. Symp. Macromol., Montreal, July 8 13, 1990: Book Abstr. Montreal, 1990, P Manjula S., Kumar V.G., Pillai.S. J. Appl. Polym. Sci., 1992, vol. 45, no. 2, pp Patent (KR) Alva K.Sh., Nayak P.L., Kumor J., Tripanthy S.K. J. Macromol. Sci. A, 1997, vol. 34, no. 4, pp Kim Y.H., Won K., Kwon J.M., Jeong H.S., Park S.Y., An E.S., Song B.K. J. Mol. Catal. B, 2005, vol. 34, no. 1 6, pp Chen Q., Xue H., Lin J. J. Appl. Polym. Sci., 2010, vol. 115, no. 2, pp Received December 1, 2011
DOI: /jcprm
. 2014. 4.. 219 227. DOI: 10.14258/jcprm.201404232 544.4:674.03:678. 1*,. 1,. 2 1,, 21,,, 622012 ( ), -mail: shishlov@ucp.ru 2,, 37,, 620100 ( ), -mail: vvg@usfeu.ru. -. -,,. - ( ). :,,,,, -. -, -, [1,
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