Structure and Properties of Gallic Acid Epoxy Modified Gelatin

HAN Qinggang; ZHANG Xi; GAO Shiyu; LI Kexin; HUANG Ganhui

doi:10.13386/j.issn1002-0306.2023020047

Volume 44 Issue 23

Nov. 2023

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2023 > 44(23): 53-60. > DOI: 10.13386/j.issn1002-0306.2023020047

HAN Qinggang, ZHANG Xi, GAO Shiyu, et al. Structure and Properties of Gallic Acid Epoxy Modified Gelatin[J]. Science and Technology of Food Industry, 2023, 44(23): 53−60. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023020047.

Citation:

PDF (3749 KB)

Structure and Properties of Gallic Acid Epoxy Modified Gelatin

State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China

More Information

Received Date: February 06, 2023
Available Online: October 08, 2023

Graphical Abstract

Abstract

Abstract

In this study, gallic acid (GA) was used to synthesize the gallic acid epoxy (GAE) for the chemical modification of gelatin. The chemical structure, hydration properties, thermal stability, and mechanical properties of GAE modified gelatin (GAEG) were evaluated. It was found that the epoxy group of GAE reacted with the primary amine group of gelatin to form C-N bond and covalent cross-linking. The swelling ratio of GAEG in water was increased by about 5 times. With the cross-linking degree increased from 41.13% to 72.68%, the swelling ratio decreased from 7831% to 6448%. While the gelatin dissolved completely in water within 24 h, the GAEG film remained intact for 7 days, and the disintegration rate decreased significantly with the increase of cross-linking degree. The water contact angle decreased from 88.01° to 59.87° after the modification, indicating increased hydrophilicity. The reduction of dehydration rate and the increase in total dehydration ratio suggested that the water retention capacity has been improved after the modification. The denaturation temperature increased from 55.0 ℃ to 61.7 ℃, and the thermal decomposition temperature increased from 240 ℃ to 274 ℃, with a relative decrease in thermal weight loss. The modification treatment led to a slight decrease in mechanical properties. This study demonstrated that GAE improved the hydration properties and thermal stability of gelatin, contributed to the application of gelatin as water retaining agent and stabilizer in food industry.
- gelatin,
- gallic acid,
- epoxy,
- chemical cross-linking,
- physicochemical property

FullText(HTML)

References (32)

References

[1]	RATHER J A, AKHTER N, ASHRAF Q S, et al. A comprehensive review on gelatin:Understanding impact of the sources, extraction methods, and modifications on potential packaging applications[J]. Food Packaging and Shelf Life,2022,34:100945. doi: 10.1016/j.fpsl.2022.100945
[2]	ALIPAL J, MOHD PU’AD N A S, LEE T C, et al. A review of gelatin:Properties, sources, process, applications, and commercialisation[J]. Materials Today: Proceedings,2021,42:240−250. doi: 10.1016/j.matpr.2020.12.922
[3]	TANG C, ZHOU K, ZHU Y, et al. Collagen and its derivatives:from structure and properties to their applications in food industry[J]. Food Hydrocolloids,2022,131:107748. doi: 10.1016/j.foodhyd.2022.107748
[4]	ERGE A, EREN Ö. Chicken gelatin modification by caffeic acid:A response surface methodology investigation[J]. Food Chemistry,2021,351:129269. doi: 10.1016/j.foodchem.2021.129269
[5]	马东, 石梦瑶, 朱贺, 等. 明胶基生物可降解薄膜的研究进展[J]. 食品工业科技,2021,42(11):365−371. [MA D, SHI M Y, ZHU H, et al. Research progress of gelatin-based biodegradable films[J]. Science and Technology of Food Industry,2021,42(11):365−371. doi: 10.13386/j.issn1002-0306.2020060256 MA D, SHI M Y, ZHU H, et al. Research progress of gelatin-based biodegradable films[J]. Science and Technology of Food Industry, 2021, 42（11）: 365−371. doi: 10.13386/j.issn1002-0306.2020060256
[6]	ZHANG X, DO M D, CASEY P, et al. Chemical modification of gelatin by a natural phenolic cross-linker, tannic acid[J]. Journal of Agricultural and Food Chemistry,2010,58(11):6809−6815. doi: 10.1021/jf1004226
[7]	STOESSEL P R, KREBS U, HUFENUS R, et al. Porous, water-resistant multifilament yarn spun from gelatin[J]. Biomacromolecules,2015,16(7):1997−2005. doi: 10.1021/acs.biomac.5b00424
[8]	郭华, 史泽毅, 张海霞, 等. 明胶-柠檬酸-硬脂酸复合凝胶的制备及性能[J]. 现代食品科技,2021,37(10):171−179,307. [GUO H, SHI Y Z, ZHANG H X, et al. Preparation and properties of gelatin-citric acid-stearic acid composite gel[J]. Modern Food Science and Technology,2021,37(10):171−179,307. doi: 10.13982/j.mfst.1673-9078.2021.10.0183 GUO H, SHI Y Z, ZHANG H X, et al. Preparation and properties of gelatin-citric acid-stearic acid composite gel[J]. Modern Food Science and Technology, 2021, 37（10）: 171−179,307. doi: 10.13982/j.mfst.1673-9078.2021.10.0183
[9]	SKOPINSKA-WISNIEWSKA J, TUSZYNSKA M, OLEWNIK-KRUSZKOWSKA E. Comparative study of gelatin hydrogels modified by various cross-linking agents[J]. Materials,2021,14(2):396. doi: 10.3390/ma14020396
[10]	张单单, 白鸽, 王琳, 等. 戊二醛改性明胶耐酶解条件的优化[J]. 食品工业科技,2016,37(6):133−136,141. [ZHANG D D, BAI G, WANG L, et al. Optimizing conditions of the modified gelatin with glutaraldehyde resistant to enzymatic hydrolysis[J]. Science and Technology of Food Industry,2016,37(6):133−136,141. doi: 10.13386/j.issn1002-0306.2016.06.018 ZHANG D D, BAI G, WANG L, et al. Optimizing conditions of the modified gelatin with glutaraldehyde resistant to enzymatic hydrolysis[J]. Science and Technology of Food Industry, 2016, 37（6）: 133−136,141. doi: 10.13386/j.issn1002-0306.2016.06.018
[11]	WANG Z, CHEN Y, CHEN S, et al. Preparation and characterization of a soy protein based bio-adhesive crosslinked by waterborne epoxy resin and polyacrylamide[J]. RSC Advances,2019,9(60):35273−35279. doi: 10.1039/C9RA05931H
[12]	SHUNDO A, YAMAMOTO S, TANAKA K. Network formation and physical properties of epoxy resins for future practical applications[J]. JACS Au,2022,2(7):1522−1542. doi: 10.1021/jacsau.2c00120
[13]	ZENG Y, XU P, YANG W, et al. Soy protein-based adhesive with superior bonding strength and water resistance by designing densely crosslinking networks[J]. European Polymer Journal,2021,142:110128. doi: 10.1016/j.eurpolymj.2020.110128
[14]	KOH L, ISLAM M, MITRA D, et al. Epoxy cross-linked collagen and collagen-laminin peptide hydrogels as corneal substitutes[J]. Journal of Functional Biomaterials,2013,4(3):162−177. doi: 10.3390/jfb4030162
[15]	ZHENG X, CHEN Y, DAN N, et al. Highly stable collagen scaffolds crosslinked with an epoxidized natural polysaccharide for wound healing[J]. International Journal of Biological Macromolecules,2021,182:1994−2002. doi: 10.1016/j.ijbiomac.2021.05.189
[16]	MA S, LI T, LIU X, et al. Research progress on bio-based thermosetting resins:Research progress on bio-based thermosetting resins[J]. Polymer International,2016,65(2):164−173. doi: 10.1002/pi.5027
[17]	ROCHESTER J R, BOLDEN A L, KWIATKOWSKI C F. Prenatal exposure to bisphenol A and hyperactivity in children:A systematic review and meta-analysis[J]. Environment International,2018,114:343−356. doi: 10.1016/j.envint.2017.12.028
[18]	WAN J, ZHAO J, ZHANG X, et al. Epoxy thermosets and materials derived from bio-based monomeric phenols:Transformations and performances[J]. Progress in Polymer Science,2020,108:101287. doi: 10.1016/j.progpolymsci.2020.101287
[19]	NOURAH A A Z, REDA M El-S, ABDULLAH M A. Recent developments of gallic acid derivatives and their hybrids in medicinal chemistry:A review[J]. European Journal of Medicinal Chemistry,2020,204:112609. doi: 10.1016/j.ejmech.2020.112609
[20]	PATIL D M, PHALAK G A, MHASKE S T. Synthesis of bio-based epoxy resin from gallic acid with various epoxy equivalent weights and its effects on coating properties[J]. Journal of Coatings Technology and Research,2017,14(2):355−365. doi: 10.1007/s11998-016-9853-x
[21]	AOUF C, NOUAILHAS H, FACHE M, et al. Multi-functionalization of gallic acid. synthesis of a novel bio-based epoxy resin[J]. European Polymer Journal,2013,49(6):1185−1195. doi: 10.1016/j.eurpolymj.2012.11.025
[22]	YU N, LI J, MA F, et al. Preparation and properties of cationic gelatin cross-linked with tannin[J]. Journal of Agricultural and Food Chemistry,2020,68(35):9537−9545. doi: 10.1021/acs.jafc.0c01131
[23]	FENG Y, HU Y, MAN L, et al. Biobased thiol-epoxy shape memory networks from gallic acid and vegetable oils[J]. European Polymer Journal,2019,112:619−628. doi: 10.1016/j.eurpolymj.2018.10.025
[24]	CAO L, LIU X, NA H, et al. How a bio-based epoxy monomer enhanced the properties of diglycidyl ether of bisphenol A (DGEBA)/graphene composites[J]. Journal of Materials Chemistry A,2013,1(16):5081−5088. doi: 10.1039/c3ta01700a
[25]	CHEN S, LÜ S, HOU G, et al. Mechanical and thermal properties of biphenyldiol formaldehyde resin/gallic acid epoxy composites enhanced by graphene oxide[J]. Journal of Applied Polymer Science,2015,132(41):42637.
[26]	ZHENG H, ZHAO M, DONG Q, et al. Extruded transglutaminase-modified gelatin-beeswax composite packaging film[J]. Food Hydrocolloids,2022,132:107849. doi: 10.1016/j.foodhyd.2022.107849
[27]	DAI H, PENG L, WANG H, et al. Improved properties of gelatin films involving transglutaminase cross-linking and ethanol dehydration:The self-assembly role of chitosan and montmorillonite[J]. Food Hydrocolloids,2022,132:107870. doi: 10.1016/j.foodhyd.2022.107870
[28]	LIU L, JIANG J, JIN X, et al. Epoxide Cross-linked and lysine-blocked zein ultrafine fibrous scaffolds with prominent wet stability and cytocompatibility[J]. ACS Applied Polymer Materials,2021,3(8):3855−3866. doi: 10.1021/acsapm.1c00439
[29]	王晓婷, 康明丽, 宋丽君, 等. 单宁酸改性明胶脂肪替代物结构及功能性质的研究[J]. 食品工业科技,2022,43(11):104−111. [WANG X T, KANG M L, SONG L J, et al. Study on structure and functional properties of tannic acid modified gelatin fat substitute[J]. Science and Technology of Food Industry,2022,43(11):104−111. doi: 10.13386/j.issn1002-0306.2021090109 WANG X T, KANG M L, SONG L J, et al. Study on structure and functional properties of tannic acid modified gelatin fat substitute[J]. Science and Technology of Food Industry, 2022, 43（11）: 104−111. doi: 10.13386/j.issn1002-0306.2021090109
[30]	WANG P, WANG Y, HONG P, et al. Di-aldehyde starch crystal:A novel bio-crosslinker for strengthening the structure and physio-chemical properties of gelatin-based films[J]. Food Bioscience,2021,43:101308. doi: 10.1016/j.fbio.2021.101308
[31]	章林溪, 易唯奇. 类蛋白质分子的二级结构对力学行为的影响[J]. 高分子学报,2005(5):745−749. [ZHANG L X, YI W Q. Effect of secondary structure on mechanical behavior of protein-like molecules[J]. Acta Polymerica Sinica,2005(5):745−749. doi: 10.3321/j.issn:1000-3304.2005.05.020 ZHANG L X, YI W Q. Effect of secondary structure on mechanical behavior of protein-like molecules[J]. Acta Polymerica Sinica, 2005（5）: 745−749. doi: 10.3321/j.issn:1000-3304.2005.05.020
[32]	钱迅南. 丝素蛋白/角蛋白复合材料的制备与性能研究[D]. 杭州:浙江理工大学, 2020. [QIAN X N. Study on preparation and properties of silk fibroin/keratin composite[D]. Hangzhou:Zhejiang Sci-Tech University, 2020. QIAN X N. Study on preparation and properties of silk fibroin/keratin composite[D]. Hangzhou: Zhejiang Sci-Tech University, 2020.

[1]	LIAO Suqi, WANG Lijun, XIA Xianghua, FU Jin'e, WEI Shugen, LONG Hairong. Determination and Evaluation of Nutritional Components in Stem and Leaves of Kadsura cocinea[J]. Science and Technology of Food Industry, 2021, 42(5): 289-294. DOI: 10.13386/j.issn1002-0306.2020040276
[2]	TIAN Jing, LI Qiao-ling. Rapid Determination of Citric Acid and L-malic Acid Content for Pear Juice by Near Infrared Spectroscopy[J]. Science and Technology of Food Industry, 2018, 39(20): 227-232. DOI: 10.13386/j.issn1002-0306.2018.20.038
[3]	FU Qun, ZHAO Hong-hua, LIU Feng, REN Hong-bo, WEI Jun-qing, CHEN Guo-feng. Determination of five pesticides residues in wild vegetables by ultra performance liquid chromatography-tandem mass spectrometry[J]. Science and Technology of Food Industry, 2017, (15): 238-243. DOI: 10.13386/j.issn1002-0306.2017.15.044
[4]	XU Rui, TAN Hong, YANG Hong-bo, SUN Hai-da, HE Jin-lin. Determination of seven perfluorinated compounds in fast food papers by solid phase extraction couple with solid phase extraction and liquid chromatography-mass spectrometry[J]. Science and Technology of Food Industry, 2015, (06): 49-52. DOI: 10.13386/j.issn1002-0306.2015.06.001
[5]	HE Ming- feng, ZHOU Jian-wei, LIU Dong-hong. Review on migration and determination of bisphenol A and its epoxy derivatives in food can coatings[J]. Science and Technology of Food Industry, 2015, (01): 381-385. DOI: 10.13386/j.issn1002-0306.2015.01.072
[6]	WU Ying, ZHANG Hui, CUI Fang, JIANG Jie. Determination of Urotropine in dried beancurd sticks by ultra performance liquid chromatography-tandem mass spectrometry[J]. Science and Technology of Food Industry, 2014, (17): 298-300. DOI: 10.13386/j.issn1002-0306.2014.17.057
[7]	ZHOU Hong-xia, HUA Chun, TANG Hui-min. Determination of 20 pthalates in feed by Gas Chromatography-Mass Spectrometry[J]. Science and Technology of Food Industry, 2014, (10): 74-78. DOI: 10.13386/j.issn1002-0306.2014.10.007
[8]	WU Jing, LEI Hong-tao, SHEN Yu-dong, WANG Hong, YANG Jin-yi, SUN Yuan-ming, XU Zhen-lin. Trends in the determination of trace acrylamide in food products[J]. Science and Technology of Food Industry, 2013, (23): 380-385. DOI: 10.13386/j.issn1002-0306.2013.23.073
[9]	LI Chun-li, ZHU Xue-liang. Simultaneous determination of 16 kinds of phathalate plasticizers in wine by gas chromatography /triple quadrupole mass spectrometry[J]. Science and Technology of Food Industry, 2013, (21): 310-312. DOI: 10.13386/j.issn1002-0306.2013.21.083
[10]	YUAN Shi-lin, SHANG Yu, QIU Yang. A new method on determination of the total sugar content in edible fungi[J]. Science and Technology of Food Industry, 2013, (18): 78-79. DOI: 10.13386/j.issn1002-0306.2013.18.044