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Polymer Bulletin

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30-01-2022 | Original Paper

Surface modification of film chitosan materials with aldehydes for wettability and biodegradation control

Authors: Ekaterina Bryuzgina, Vitaliya Yartseva, Evgeny Bryuzgin, Oleg Tuzhikov, Alexander Navrotskiy

Published in: Polymer Bulletin | Issue 1/2023

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Abstract

Chitosan is one of the prospective polymers for use in regenerative medicine which has unique properties such as biocompatibility, biodegradability, antimicrobial, anti-inflammatory, and antitumor potency. In this article, we study the peculiarities of the surface modification of chitosan films with carbonyl-containing compounds, which differed both in molecular characteristics and in their hydrophilic and hydrophobic properties. The potential for controlling the biodegradation of the resulting materials has been established, which can be used in the creation of wound dressings. Both the destruction time and lyophilic properties of the surface depend on the length of the modifier’s hydrocarbon radical. The contact angle and water absorption of obtained film materials correlate with hydrophobicity, which estimated by the calculated value of the hydrophilic–lipophilic balance. The cytotoxicity of modified chitosan films was studied, and it was found that they are non-toxic (cytotoxic index of < 50%) for human skin cell cultures, which shows their potential for use in the creation of materials for skin protection and external wound healing.

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da Silva D, Kaduri M, Poley M et al (2018) Biocompatibility, biodegradation and excretion of polylactic acid (PLA) in medical implants and theranostic systems. Chem Eng J 340:9–14. https://doi.org/10.1016/j.cej.2018.01.010CrossRef

Hong Y, Gong Y, Gao C, Shen J (2008) Collagen-coated polylactide microcarriers/chitosan hydrogel composite: injectable scaffold for cartilage regeneration. J Biomed Mater Res - Part A 85:628–637. https://doi.org/10.1002/jbm.a.31603CrossRef

Muzzarelli RAA, Biagini G, Bellardini M et al (1993) Osteoconduction exerted by methylpyrrolidinone chitosan used in dental surgery. Biomaterials 14:39–43. https://doi.org/10.1016/0142-9612(93)90073-BCrossRef

Da Silva CM, Da Silva DL, Modolo LV et al (2011) Schiff bases: A short review of their antimicrobial activities. J Adv Res 2:1–8. https://doi.org/10.1016/j.jare.2010.05.004CrossRef

Wan Y, Wu H, Yu A, Wen D (2006) Biodegradable polylactide/chitosan blend membranes. Biomacromol 7:1362–1372. https://doi.org/10.1021/bm0600825CrossRef

Wang Y, Su Y, Wang W et al (2019) The advances of polysaccharide-based aerogels: preparation and potential application. Carbohydr Polym. https://doi.org/10.1016/j.carbpol.2019.115242CrossRef

Wan Y, Fang Y, Wu H, Cao X (2007) Porous polylactide/chitosan scaffolds for tissue engineering. J Biomed Mater Res - Part A 80:776–789. https://doi.org/10.1002/jbm.a.31025CrossRef

Wu T, Zivanovic S, Draughon FA et al (2005) Physicochemical properties and bioactivity of fungal chitin and chitosan. J Agric Food Chem 53:3888–3894. https://doi.org/10.1021/jf048202sCrossRef

Wang J, Wang L, Zhou Z et al (2016) Biodegradable polymer membranes applied in guided bone/tissue regeneration: a review. Polymers (Basel) 8:115–135. https://doi.org/10.3390/polym8040115CrossRef

10.

Singh B, Choi YJ, Park IK et al (2014) Chemical modification of chitosan with ph-sensitive molecules and specific ligands for efficient DNA transfection and siRNA silencing. J Nanosci Nanotechnol 14:564–576. https://doi.org/10.1166/jnn.2014.9079CrossRef

11.

Vroman I, Tighzert L (2009) Biodegradable polymers. Materials (Basel) 2:307–344. https://doi.org/10.3390/ma2020307CrossRef

12.

Banerjee A, Chatterjee K, Madras G (2014) Enzymatic degradation of polymers: a brief review. Mater Sci Technol 30:567–573. https://doi.org/10.1179/1743284713Y.0000000503CrossRef

13.

Hu Z-H, Yu H-Q, Zhu R-F (2005) Influence of particle size and pH on anaerobic degradation of cellulose by ruminal microbes. Int Biodeterior Biodegradation 55:233–238. https://doi.org/10.1016/j.ibiod.2005.02.002CrossRef

14.

Camacho-Muñoz R, Villada-Castillo HS, Solanilla-Duque JF (2020) Anaerobic biodegradation under slurry thermophilic conditions of poly(lactic acid)/starch blend compatibilized by maleic anhydride. Int J Biol Macromol 163:1859–1865. https://doi.org/10.1016/j.ijbiomac.2020.09.183CrossRef

15.

Nidheesh T, Gaurav Kumar P, Suresh PV (2015) Enzymatic degradation of chitosan and production of d-glucosamine by solid substrate fermentation of exo-β-d-glucosaminidase (exochitosanase) by Penicillium decumbens CFRNT15. Int Biodeterior Biodegradation 97:97–106. https://doi.org/10.1016/j.ibiod.2014.10.016CrossRef

16.

Tai C, Li S, Xu Q et al (2010) Chitosan production from hemicellulose hydrolysate of corn straw: impact of degradation products on Rhizopus oryzae growth and chitosan fermentation. Lett Appl Microbiol 51:278–284. https://doi.org/10.1111/j.1472-765X.2010.02893.xCrossRef

17.

Zhang L, Bao Y, Chen H et al (2020) Functional microbiota for polypeptide degradation during hypertonic moromi-fermentation of pixian broad bean paste. Foods 9:930. https://doi.org/10.3390/foods9070930CrossRef

18.

De AM, Rizzello CG, Fasano A et al (2006) VSL#3 probiotic preparation has the capacity to hydrolyze gliadin polypeptides responsible for Celiac Sprue probiotics and gluten intolerance. Biochim Biophys Acta - Mol Basis Dis 1762:80–93. https://doi.org/10.1016/j.bbadis.2005.09.008CrossRef

19.

Rogovina SZ, Lomakin SM, Aleksanyan KV, Prut EV (2012) The structure, properties, and thermal destruction of biodegradable blends of cellulose and ethylcellulose with synthetic polymers. Russ J Phys Chem B 6:416–424. https://doi.org/10.1134/S1990793112060048CrossRef

20.

Mamleev V, Bourbigot S, Yvon J (2007) Kinetic analysis of the thermal decomposition of cellulose: the main step of mass loss. J Anal Appl Pyrolysis 80:151–165. https://doi.org/10.1016/j.jaap.2007.01.013CrossRef

21.

Villetti MA, Crespo JS, Soldi MS et al (2002) Thermal degradation of natural polymers. J Therm Anal Calorim. https://doi.org/10.1023/A:1013902510952CrossRef

22.

Mahesh B, Kathyayani D, Nanjundaswamy GS et al (2019) Miscibility studies of plastic-mimetic polypeptide with hydroxypropylmethylcellulose blends and generation of non-woven fabrics. Carbohydr Polym 212:129–141. https://doi.org/10.1016/j.carbpol.2019.02.042CrossRef

23.

Mahesh B, Kathyayani D, Channe Gowda D, Mrutunjaya K (2020) Blends of synthetic plastic-derived polypeptide with Hydroxypropylmethylcellulose and polyvinyl alcohol: unraveling the specific interaction parameters, morphology and thermal stability of the polymers couple. J Polym Res 27:278. https://doi.org/10.1007/s10965-020-02191-5CrossRef

24.

Neto CGT, Giacometti JA, Job AE et al (2005) Thermal analysis of chitosan based networks. Carbohydr Polym 62:97–103. https://doi.org/10.1016/j.carbpol.2005.02.022CrossRef

25.

Quijada-Garrido I (2007) The role played by the interactions of small molecules with chitosan and their transition temperatures. Glass-forming liquids: 1,2,3-Propantriol (glycerol). Carbohydr Polym 68:173–186. https://doi.org/10.1016/j.carbpol.2006.07.025CrossRef

26.

Guan Y, Liu X, Zhang Y, Yao K (1998) Study of phase behavior on chitosan/viscose rayon blend film. J Appl Polym Sci 67:1965–1972. https://doi.org/10.1002/(SICI)1097-4628(19980321)67:12%3c1965::AID-APP2%3e3.0.CO;2-LCrossRef

27.

Dong Y, Ruan Y, Wang H et al (2004) Studies on glass transition temperature of chitosan with four techniques. J Appl Polym Sci 93:1553–1558. https://doi.org/10.1002/app.20630CrossRef

28.

Mucha M, Pawlak A (2005) Thermal analysis of chitosan and its blends. Thermochim Acta 427:69–76. https://doi.org/10.1016/j.tca.2004.08.014CrossRef

29.

Hsu S, Chang Y-B, Tsai C-L et al (2011) Characterization and biocompatibility of chitosan nanocomposites. Colloids Surfaces B Biointerfaces 85:198–206. https://doi.org/10.1016/j.colsurfb.2011.02.029CrossRef

30.

Sakurai K (2000) Glass transition temperature of chitosan and miscibility of chitosan/poly(N-vinyl pyrrolidone) blends. Polymer (Guildf) 41:7051–7056. https://doi.org/10.1016/S0032-3861(00)00067-7CrossRef

31.

Kean T, Thanou M (2010) Biodegradation, biodistribution and toxicity of chitosan. Adv Drug Deliv Rev 62:3–11. https://doi.org/10.1016/j.addr.2009.09.004CrossRef

32.

Bakhtiari SSE, Karbasi S, Tabrizi SAH, Ebrahimi-Kahrizsangi R (2019) Chitosan/MWCNTs composite as bone substitute: Physical, mechanical, bioactivity, and biodegradation evaluation. Polym Compos 40:E1622–E1632. https://doi.org/10.1002/pc.25104CrossRef

33.

Babicheva TS, Gegel NO, Shipovskaya AB (2017) Visualization of morphological features of chitosan microtubes during biodegradation. J Phys Conf Ser. https://doi.org/10.1088/1742-6596/917/4/042026CrossRef

34.

Aranaz I, Harris R, Navarro-García F et al (2016) Chitosan based films as supports for dual antimicrobial release. Carbohydr Polym 146:402–410. https://doi.org/10.1016/j.carbpol.2016.03.064CrossRef

35.

Liu H, Wang C, Li C et al (2018) A functional chitosan-based hydrogel as a wound dressing and drug delivery system in the treatment of wound healing. RSC Adv 8:7533–7549. https://doi.org/10.1039/c7ra13510fCrossRef

36.

Mohebbi S, Nezhad MN, Zarrintaj P et al (2018) Chitosan in biomedical engineering: a critical review. Curr Stem Cell Res Ther 14:93–116. https://doi.org/10.2174/1574888x13666180912142028CrossRef

37.

Intini C, Elviri L, Cabral J et al (2018) 3D-printed chitosan-based scaffolds: an in vitro study of human skin cell growth and an in-vivo wound healing evaluation in experimental diabetes in rats. Carbohydr Polym 199:593–602. https://doi.org/10.1016/j.carbpol.2018.07.057CrossRef

38.

Morin-Crini N, Lichtfouse E, Torri G, Crini G (2019) Applications of chitosan in food, pharmaceuticals, medicine, cosmetics, agriculture, textiles, pulp and paper, biotechnology, and environmental chemistry. Environ Chem Lett 17:1667–1692. https://doi.org/10.1007/s10311-019-00904-xCrossRef

39.

Ganesan K, Budtova T, Ratke L et al (2018) Review on the production of polysaccharide aerogel particles. Materials (Basel) 11:2144–2181. https://doi.org/10.3390/ma11112144CrossRef

40.

İlk S, Ramanauskaitė A, Koç Bilican B et al (2020) Usage of natural chitosan membrane obtained from insect corneal lenses as a drug carrier and its potential for point of care tests. Mater Sci Eng C Eng C 112:110897. https://doi.org/10.1016/j.msec.2020.110897CrossRef

41.

Takeshita S, Konishi A, Takebayashi Y et al (2017) Aldehyde approach to hydrophobic modification of chitosan aerogels. Biomacromol 18:2172–2178. https://doi.org/10.1021/acs.biomac.7b00562CrossRef

42.

Guinesi LS, Cavalheiro ÉTG (2006) Influence of some reactional parameters on the substitution degree of biopolymeric Schiff bases prepared from chitosan and salicylaldehyde. Carbohydr Polym 65:557–561. https://doi.org/10.1016/j.carbpol.2006.01.030CrossRef

43.

Dos Santos JE, Dockal ER, Cavalheiro ÉTG (2005) Synthesis and characterization of Schiff bases from chitosan and salicylaldehyde derivatives. Carbohydr Polym 60:277–282. https://doi.org/10.1016/j.carbpol.2004.12.008CrossRef

44.

Fen YW (2011) Optical properties of crosslinked chitosan thin film with glutaraldehyde using surface plasmon resonance technique. Am J Eng Appl Sci 4:61–65. https://doi.org/10.3844/ajeassp.2011.61.65CrossRef

45.

Argüelles-Monal W, Goycoolea PM, Peniche C, Higuera-Ciapara I (1998) Rheological study of the chitosan/glutaraldehyde chemical gel system. Polym Gels Netw 6:429–440. https://doi.org/10.1016/S0966-7822(98)00032-XCrossRef

46.

Ramachandran S, Nandhakumar S, Dhanaraju MD (2011) Formulation and characterization of glutaraldehyde cross-linked chitosan biodegradable microspheres loaded with famotidine. Trop J Pharm Res 10:309–316. https://doi.org/10.4314/tjpr.v10i3.13CrossRef

47.

Kyzas GZ, Bikiaris DN (2015) Recent modifications of chitosan for adsorption applications: a critical and systematic review. Mar Drugs 13:312–337. https://doi.org/10.3390/md13010312CrossRef

48.

Poon L, Wilson LD, Headley JV (2014) Chitosan-glutaraldehyde copolymers and their sorption properties. Carbohydr Polym 109:92–101. https://doi.org/10.1016/j.carbpol.2014.02.086CrossRef

49.

Kimura S, Isobe N, Wada M et al (2011) Enzymatic hydrolysis of chitosan-dialdehyde cellulose hydrogels. Carbohydr Polym 83:1850–1853. https://doi.org/10.1016/j.carbpol.2010.10.049CrossRef

50.

Monteiro OAC Jr, Airoldi C (1999) Some studies of crosslinking chitosan-glutaraldehyde interaction in a homogeneous system. Int J Biol Macromol 26:119–128. https://doi.org/10.1016/S0141-8130(99)00068-9CrossRef

51.

Liu Y, Shen X, Zhou H et al (2016) Chemical modification of chitosan film via surface grafting of citric acid molecular to promote the biomineralization. Appl Surf Sci 370:270–278. https://doi.org/10.1016/j.apsusc.2016.02.124CrossRef

52.

Vallapa N, Wiarachai O, Thongchul N et al (2011) Enhancing antibacterial activity of chitosan surface by heterogeneous quaternization. Carbohydr Polym 83:868–875. https://doi.org/10.1016/j.carbpol.2010.08.075CrossRef

53.

Marin L, Ailincai D, Mares M et al (2015) Imino-chitosan biopolymeric films. Obtaining, self-assembling, surface and antimicrobial properties. Carbohydr Polym 117:762–770. https://doi.org/10.1016/j.carbpol.2014.10.050CrossRef

54.

Chernyshova EB, Berezin AS, Tuzhikov OI (2017) Hydrophobization of chitosan-based films with acrolein. Russ J Appl Chem 90:1165–1170. https://doi.org/10.1134/S1070427217070229CrossRef

55.

Yudin VE, Dobrovolskaya IP, Neelov IM et al (2014) Wet spinning of fibers made of chitosan and chitin nanofibrils. Carbohydr Polym 108:176–182. https://doi.org/10.1016/j.carbpol.2014.02.090CrossRef

56.

Klotzbach T, Watt M, Ansari Y, Minteer SD (2006) Effects of hydrophobic modification of chitosan and Nafion on transport properties, ion-exchange capacities, and enzyme immobilization. J Memb Sci 282:276–283. https://doi.org/10.1016/j.memsci.2006.05.029CrossRef

57.

Bryuzgin EV, Klimov VV, Repin SA et al (2017) Aluminum surface modification with fluoroalkyl methacrylate-based copolymers to attain superhydrophobic properties. Appl Surf Sci 419:454–459. https://doi.org/10.1016/j.apsusc.2017.04.222CrossRef

58.

Davies JT (1957) A quantitative kinetic theory of emulsion type. I. Physical chemistry of the emulsifying agent. A Quantitative Kinet Theory Emuls Type I Phys Chem Emuls Agent 1:426–438

59.

Calmon-Decriaud A, Bellon-Maurel V, Silvestre F (1998) Standard methods for testing the aerobic biodegradation of polymeric materials. Review and perspectives. Blockcopolym-Polyelectro-Biodegrad 135:207–226. https://doi.org/10.1007/3-540-69191-X_3

60.

Popryadukhin PV, Dobrovolskaya IP, Yudin VE et al (2012) Composite materials based on chitosan and montmorillonite: prospects for use as a matrix for cultivation of stem and regenerative cells. Cell tissue biol 6:82–88. https://doi.org/10.1134/S1990519X12010099CrossRef

61.

El-Hefian EA, Elgannoudi ES, Mainal A, Yahaya AH (2010) Characterization of chitosan in acetic acid: rheological and thermal studies. Turkish J Chem 34:47–56. https://doi.org/10.3906/kim-0901-38CrossRef

62.

Park SY, Marsh KS, Rhim JW (2002) Characteristics of different molecular weight chitosan films affected by the type of organic solvents. J Food Sci 67:194–197. https://doi.org/10.1111/j.1365-2621.2002.tb11382.xCrossRef

63.

Boinovich LB, Emelyanenko AM (2008) Hydrophobic materials and coatings: principles of design, properties and applications. Russ Chem Rev 77:583–600. https://doi.org/10.1070/rc2008v077n07abeh003775CrossRef

64.

Ma J, Choudhury NA, Sahai Y, Buchheit RG (2011) A high performance direct borohydride fuel cell employing cross-linked chitosan membrane. J Power Sour 196:8257–8264. https://doi.org/10.1016/j.jpowsour.2011.06.009CrossRef

Title: Surface modification of film chitosan materials with aldehydes for wettability and biodegradation control
Authors: Ekaterina Bryuzgina
Vitaliya Yartseva
Evgeny Bryuzgin
Oleg Tuzhikov
Alexander Navrotskiy
Publication date: 30-01-2022
Publisher: Springer Berlin Heidelberg
Published in: Polymer Bulletin / Issue 1/2023
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI: https://doi.org/10.1007/s00289-021-04039-4

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