Synthesis, characterization, and performance of a novel polymeric cationic surfactant based on low molecular weight chitosan and 3-chloro-2-hydroxypropyl dimethyl dehydroabietyl ammonium chloride (CHPDMDHA)

Journal of Surfactants and Detergents

Volumn 18, Issue 3, 2015, Pages 463-470

  Qi, Fan ^a,b   Cai, Zhao Sheng ^a   Zhu, Xue Mei ^a   Shang, Shi Bing ^b   Pei, Li Jun ^b  

^a YANCHENG INSTITUTE OF TECHNOLOGY   (China)

^b RESEARCH INSTITUTE OF FORESTRY   (China)

Author keywords

Aggregate behavior; Emulsifying property; Low molecular weigh chitosan; Polymeric cationic surfactants; Surface activities

Indexed keywords

AGGLOMERATION; AGGREGATES; BIOPHYSICS; CHITIN; CHITOSAN; CHLORINE COMPOUNDS; CRITICAL MICELLE CONCENTRATION; DYES; EMULSIFICATION; EMULSIONS; GRAFTING (CHEMICAL); MOLECULAR WEIGHT; POLYMERS; SOLUTIONS; SURFACE ACTIVE AGENTS; SURFACE TENSION; TRANSMISSION ELECTRON MICROSCOPY;

AGGREGATE BEHAVIOR; AGGREGATION BEHAVIOR; AMMONIUM CHLORIDE; CRITICAL MICELLE CONCENTRATION (CMC); EMULSIFYING PROPERTY; LOW MOLECULAR WEIGHT CHITOSANS; SURFACE ACTIVITIES;

CATIONIC SURFACTANTS;

EID: 84939952390     PISSN: 10973958     EISSN: 15589293     Source Type: Journal    
DOI: 10.1007/s11743-015-1676-8     Document Type: Article

References (48)

1. Shahidi F, Arachchi JKV, Jeon Y-J (1999) Food applications of chitin and chitosans. Trends Food Sci Tech 10:37-51
2. Cravotto G, Tagliapietra S, Robaldo B, Trotta M (2005) Chemical modification of chitosan under high-intensity ultrasound. Sonochem 12:95-98
3. Philippova OE, Korchagina EV, Volkov EV, Smirnov VA, Khokhlov AR, Rinaudo M (2012) Aggregation of some water-soluble derivatives of chitin in aqueous solutions: role of the degree of acetylation and effect of hydrogen bond breaker. Carbohydr Polym 87:687-694
4. Rinaudo M (2006) Chitin and chitosan: properties and applications. Prog Polym Sci 31:603-632
5. Dash M, Chiellini F, Ottenbrite RM, Chiellini E (2011) Chitosan - a versatile semi-synthetic polymer in biomedical applications. Prog Polym Sci 36:981-1014
6. Kumar R, Muzzarelli MNV, Muzzarelli RAA, Sashiwa CH, Domb AJ (2004) Chitosan chemistry and pharmaceutical perspectives. Chem Rev 104:6017-6084
7. Alves NM, Mano JF (2008) Chitosan derivatives obtained by chemical modifications for biomedical and environmental applications. Int J Biol Macromol 43:401-414
8. Crini G, Badot PM (2008) Application of chitosan, a natural aminopolysaccharide, for dye removal from aqueous solutions by adsorption processes using batch studies: a review of recent literature. Prog Polym Sci 33:399-447
9. Wibowo S, Velazquez G, Savant V, Torres JA (2007) Effect of chitosan type on protein and water recovery efficiency from surimi wash water treated with chitosan-alginate complexes. Bioresour Technol 98:539-545
10. Ashori A, Raverty WD, Vanderhoek N, Ward JV (2008) Surface topography of kenaf (Hibiscus cannabinus) sized papers. Bioresour Technol 99:404-410
11. Xia W, Liu P, Liu J (2008) Advance in chitosan hydrolysis by non-specific cellulases. Bioresour Technol 99:6751-6762
12. Wang W, Du Y, Qiu Y, Wang X, Hu Y, Yang J, Cai J, Kennedy JF (2008) A new green technology for direct production of low molecular weight chitosan. Carbohydr Polym 74:127-132
13. Prasertsung I, Damrongsakkul S, Terashima C, Saito N, Takai O (2012) Preparation of low molecular weight chitosan using solution plasma system. Carbohydr Polym 87:2745-2749
14. Mai-ngam K (2006) Comblike poly(ethylene oxide)/hydrophobic C6 branched chitosan surfactant polymers as anti-infection surface modifying agents. Colloids Surf B Biointerfaces 49:117-125
15. Tikhonov VE, Stepnova EA, Babak VG, Yamskov IA, Palma-Guerrero J, Jansson H-B, Lopez-Llorca LV, Salinas J, Gerasimenko DV, Avdienko ID, Varlamov VP (2006) Bactericidal and antifungal activities of a low molecular weight chitosan and its N-/2(3)-(dodec-2-enyl) succinoyl/-derivatives. Carbohydr Polym 64:66-72
16. Yakovlev GI, Mitkevich VA, Struminskaya NK, Varlamov VP, Makarov AA (2007) Low molecular weight chitosan is an efficient inhibitor of ribonucleases. Biochem Biophys Res Commun 357:584-588
17. Huang K-S, Wu W-J, Chen J-B, Lian H-S (2008) Application of low-molecular-weight chitosan in durable press finishing. Carbohydr Polym 73:254-260
18. Chung Y-C, Chen C-Y (2008) Antibacterial characteristics and activity of acid-soluble chitosan. Bioresour Technol 99:2806-2814
19. Xiang Y, Si J, Zhang Q, Liu Y, Guo H (2009) Homogeneous graft copolymerization and characterization of novel artificial glycoprotein: chitosan-poly(l-tryptophan) copolymers with secondary structural side chains. J Polym Sci Part A Polym Chem 47:925-934
20. Jin YH, Hu HY, Qiao MX, Zhu J, Qi JW, Hu CJ, Zhang Q, Chen DW (2012) pH-sensitive chitosan-derived nanoparticles as doxorubicin carriers for effective anti-tumor activity: preparation and in vitro evaluation. Colloids Surf B Biointerfaces 94:184-191
21. Huang Y-C, Jan J-S (2014) Carboxylmethyl chitosan-graft-poly(g-benzyl-l-glutamate) glycopeptides: synthesis and particle formation as encapsulants. Polymer 55:540-549
22. Sagnella S, Mai-Ngam K (2005) Chitosan based surfactant polymers designed to improve blood compatibility on biomaterials. Colloids Surf B Biointerfaces 42:147-155
23. Yao Z, Zhang C, Ping Q, Yu L (2007) A series of novel chitosan derivatives: synthesis, characterization and micellar solubilization of paclitaxel. Carbohydr Polym 68:781-792
24. Chen X, Ding S, Qu G, Zhang C (2008) Synthesis, characterization of novel chitosan derivatives and micellar solubilization of cyclosporine A. J Bioact Compat Polym 23:563-578
25. Yoksan R, Akashi M (2009) Low molecular weight chitosan-g-l-phenylalanine: preparation, characterization, and complex formation with DNA. Carbohydr Polym 75:95-103
26. Liu J, Li H, Jiang X, Zhang C, Ping Q (2010) Novel pH-sensitive chitosan-derived micelles loaded with paclitaxel. Carbohydr Polym 82:432-439
27. Huo M, Zhang Y, Zhou J, Zou A, Li J (2011) Formation, microstructure, biodistribution and absence of toxicity of polymeric micelles formed by N-octyl-N,O-carboxymethyl chitosan. Carbohydr Polym 83:1959-1969
28. Rinaudo M (2011) New amphiphilic grafted copolymers based on polysaccharides. Carbohydr Polym 83:1338-1344
29. Zhang W, Du Z, Wang W, Li G (2012) Aggregation behavior of amphiphic comb-like copolymer containing poly(ethylene oxide) methyl ether grafts. Colloids Surf A Physicochem Eng Asp 395:175-182
30. Shu H-Y, Tang X-H, Fu R-H (2004) Graft copolymer of dimethyldiallylammonium chloride onto chitosan. Chin J Appl Chem 21:734-736
31. Lee M-Y, Hong K-J, Kajiuchi T, Yang J-W (2005) Synthesis of chitosan-based polymeric surfactants and their adsorption properties for heavy metals and fatty acids. Int J Biol Macromol 36:152-158
32. Jiang G, Quan D, Liao K, Wang H (2006) Preparation of polymeric micelles based on chitosan bearing a small amount of highly hydrophobic groups. Carbohydr Polym 66:514-520
33. Sui W, Yin C, Chen Y, Zhang Z, Kong X (2006) Self-assembly of an amphiphilic derivative of chitosan and micellar solubilization of puerarin. Colloids Surf B Biointerfaces 48:13-16
34. Elsabee MZ, Morsi RE, Al-Sabagh AM (2009) Surface active properties of chitosan and its derivatives. Colloids Surf B Biointerfaces 74:1-16
35. Sajomsang W, Gonil P, Ruktanonchai UR, Pimpha N, Sramala I, Nuchuchua O, Saesoo S, Chaleawlert-umpon S, Puttipipatkhachorn S (2011) Self-aggregates formation and mucoadhesive property of water-soluble β-cyclodextrin grafted with chitosan. Int J Biol Macromol 48:589-595
36. Wang C-C, Lin L-H, Lee H-T, Ye Y-W (2011) Surface activity and micellization properties of chitosan-succinyl derivatives. Colloids Surf A Physicochem Eng Asp 389:246-253
37. Sarkar K, Kundu PP (2012) Preparation of low molecular weight N-maleated chitosan-graft-PAMAM copolymer for enhanced DNA complexation. Int J Biol Macromol 51:859-867
38. Piispanen PS, Hedman B, Norin T (2002) Synthesis and characterization of dehydroabietic acid derivatives suitable for surfactant synthesis. J Surfactant Deterg 5:165-168
39. Gottstein WJ, Cheney LC (1965) Dehydroabietylamine - a new resolving agent. J Org Chem 30:2072-2073
40. Pei L, Cai Z, Song Z, Zhu X, Shang S (2014) 3-Chloro-2-hydroxypropyl dimethyl dehydroabietyl ammonium chloride: synthesis, characterization, and physicochemical properties. J Surfactant Deterg 17:493-499
41. Qin C, Xiao L, Du Y, Shi X, Chen J (2002) A new cross-linked quaternized-chitosan resin as the support of borohydride reducing agent. React Funct Polym 50:165-171
42. Hong P, Fa C, Wei Y, Sen Z (2007) Surface properties and synthesis of the cellulose-based amphoteric polymeric surfactant. Carbohydr Polym 69:625-630
43. Cai Z-S, Song Z-Q, Shang S-B, Yang C-S (2007) Study on the flocculating properties of quaternized carboxymethyl chitosan. Polym Bull 2007(59):655-665
44. Cai Z-S, Yang C-S, Zhu X-M (2010) Preparation of quaternized carboxymethyl chitosan and its capacity to flocculate COD from printing wastewater. J Appl Polym Sci 118:299-305
45. Wu H, Zhang J, Xiao B, Zan X, Gao J, Wan Y (2011) N-(2-hydroxypropyl)-3-trimethylammonium chitosan-poly(ε-caprolactone) copolymers and their antibacterial activity. Carbohydr Polym 83:824-830
46. Muñoz-Bonilla A, Fernández-García M (2012) Polymeric materials with antimicrobial activity. Prog Polym Sci 37:281-339
47. Hebeish A, Higazy A, El-Shafei A, Sharaf S (2010) Synthesis of carboxymethyl cellulose (CMC) and starch-based hybrids and their applications in flocculation and sizing. Carbohydr Polym 79:60-69
48. Zamana M, Xiao H, Chibante F, Ni Y (2012) Synthesis and characterization of cationically modified nanocrystalline cellulose. Carbohydr Polym 89:163-170