Skip to main content
Top
Published in: Journal of Polymer Research 1/2024

01-01-2024 | Original Paper

An eco-friendly sustainable plasticizer from isosorbide and nonanoic acid: synthesis and application

Authors: T. Song, L. Ren, W. B. Li, Q. Liu, Y. X. Qin, Y. L. Zhang, Y. B. Wang, Y. D. Shen, W. N. Du, M. Y. Zhang

Published in: Journal of Polymer Research | Issue 1/2024

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

In this contribution, isosorbide dinonanoate (SDN), an environmentally sustainable plasticizer for polypropylene (PP), is successfully synthesized by virtue of esterification reaction using isosorbide and nonanoic acid with the reaction temperature of 120 °C, and the reaction time of 5 h. When the corporation of plasticizer SDN into PP matrix is the value of 15 phr, the impact strength of PP blends reaches 121 J/m, the dramatically increase of 384% compare to that of PP. DMA results shows that the glass transition temperature (Tg) of PP blends gradually decline with the increasing amount of SDN, indicating the efficient plasticization action of the SDN. It is suggested that SDN can be feasibly inserted into the non-polar matrix and then more evenly dispersed in matrix, herein, it will increase the distance between the polymer chains, improving the mobility of the molecular chains and the processing performance of the polymers. Furthermore, the plasticizing effect and environmental friendliness of SDN can be a potential replacement for o-phenyl plasticizers in the industry in the future.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference Zhu J, Liu XQ (2018) Bio-based polymer materials. Science Press, Beijing Zhu J, Liu XQ (2018) Bio-based polymer materials. Science Press, Beijing
2.
go back to reference Bocque M, Voirin C, Lapinte V, Caillol S, Robin JJ (2016) Petro-based and bio-based plasticizers: Chemical structures to Plasticizing properties. J Polym Sci A Polym Chem 54:11–33CrossRef Bocque M, Voirin C, Lapinte V, Caillol S, Robin JJ (2016) Petro-based and bio-based plasticizers: Chemical structures to Plasticizing properties. J Polym Sci A Polym Chem 54:11–33CrossRef
4.
go back to reference Daniels PH (2009) A brief overview of theories of PVC plasticization and methods used to evaluate PVC-plasticizer interaction. J Vinyl Addit Technol 15:219–223CrossRef Daniels PH (2009) A brief overview of theories of PVC plasticization and methods used to evaluate PVC-plasticizer interaction. J Vinyl Addit Technol 15:219–223CrossRef
5.
go back to reference Latini G, Felice CD, Verrotti A (2004) Plasticizers, infant nutrition and reproductive health. Reprod Toxicol 19:27–33PubMedCrossRef Latini G, Felice CD, Verrotti A (2004) Plasticizers, infant nutrition and reproductive health. Reprod Toxicol 19:27–33PubMedCrossRef
6.
go back to reference Chiellini F, Ferri M, Latini G (2011) Physical-chemical assessment of di-(2-ethylhexyl)-phthalate leakage from poly(vinyl chloride) endotracheal tubes after application in high-risk newborns. Int J Pharm 409:57–61PubMedCrossRef Chiellini F, Ferri M, Latini G (2011) Physical-chemical assessment of di-(2-ethylhexyl)-phthalate leakage from poly(vinyl chloride) endotracheal tubes after application in high-risk newborns. Int J Pharm 409:57–61PubMedCrossRef
7.
go back to reference Chiellini F, Ferri M, Morelli A, Dipaola L, Latini G (2013) Perspectives on alternatives to phthalate plasticized poly(vinyl chloride) in medical devices applications. Prog Polym Sci 38:1067–1088CrossRef Chiellini F, Ferri M, Morelli A, Dipaola L, Latini G (2013) Perspectives on alternatives to phthalate plasticized poly(vinyl chloride) in medical devices applications. Prog Polym Sci 38:1067–1088CrossRef
8.
go back to reference Hines CJ, Hopf NB, Deddens JA, Silva MJ, Calafat AM (2012) Occupational exposure to diisononyl phthalate (DiNP) in polyvinyl chloride processing operations. Int Arch Occup Environ Health 85:317–325PubMedCrossRef Hines CJ, Hopf NB, Deddens JA, Silva MJ, Calafat AM (2012) Occupational exposure to diisononyl phthalate (DiNP) in polyvinyl chloride processing operations. Int Arch Occup Environ Health 85:317–325PubMedCrossRef
9.
go back to reference Lithner D, Larsson A, Dave G (2011) Environmental and health hazard ranking and assessment of plastic polymers based on chemical composition. Sci Total Environ 409:3309–3324PubMedCrossRef Lithner D, Larsson A, Dave G (2011) Environmental and health hazard ranking and assessment of plastic polymers based on chemical composition. Sci Total Environ 409:3309–3324PubMedCrossRef
11.
go back to reference Zhang Y, Mu XY, Gao RF, Geng YQ, Liu XQ, Chen XM, Wang YH, Din YB, Wang YX, He JL (2018) Foetal-neonatal exposure of Di (2-ethylhexyl) phthalate disrupts ovarian development in mice by inducing autophagy. J Hazard Mater 358:101–112PubMedCrossRef Zhang Y, Mu XY, Gao RF, Geng YQ, Liu XQ, Chen XM, Wang YH, Din YB, Wang YX, He JL (2018) Foetal-neonatal exposure of Di (2-ethylhexyl) phthalate disrupts ovarian development in mice by inducing autophagy. J Hazard Mater 358:101–112PubMedCrossRef
12.
go back to reference Wang JJ, Tian Y, Li MH, Feng YQ, Kong L, Zhang FL, Shen W (2021) Single-cell transcriptome dissection of the toxic impact of Di (2-ethylhexyl) phthalate on primordial follicle assembly. Theranostics 11:4992–5009PubMedPubMedCentralCrossRef Wang JJ, Tian Y, Li MH, Feng YQ, Kong L, Zhang FL, Shen W (2021) Single-cell transcriptome dissection of the toxic impact of Di (2-ethylhexyl) phthalate on primordial follicle assembly. Theranostics 11:4992–5009PubMedPubMedCentralCrossRef
13.
go back to reference Mekonnen T, Mussone P, Khalil H, Bressler D (2013) Progress in bio-based plastics and plasticizing modifications. J Mater Chem A Mater 1:13379–13398CrossRef Mekonnen T, Mussone P, Khalil H, Bressler D (2013) Progress in bio-based plastics and plasticizing modifications. J Mater Chem A Mater 1:13379–13398CrossRef
14.
go back to reference Meier MAR (2014) Sustainable polymers: reduced environmental impact, renewable raw materials and catalysis. Green Chem 16:1672–1672CrossRef Meier MAR (2014) Sustainable polymers: reduced environmental impact, renewable raw materials and catalysis. Green Chem 16:1672–1672CrossRef
15.
go back to reference Saygin D, Gielen DJ, Draeck M, Worrell E, Patel MK (2014) Assessment of the technical and economic potentials of biomass use for the production of steam, chemicals and polymers. Renew Sustain Energy Rev 40:1153–1167CrossRef Saygin D, Gielen DJ, Draeck M, Worrell E, Patel MK (2014) Assessment of the technical and economic potentials of biomass use for the production of steam, chemicals and polymers. Renew Sustain Energy Rev 40:1153–1167CrossRef
16.
go back to reference Plass C, Adebar N, Hiessl R, Kleber J, Grimm A, Langsch A, Otter R, Liese A, Gröger H (2021) Structure-performance guided design of sustainable plasticizers from Biorenewable Feedstocks. Eur J Org Chem 2021:6086–6096CrossRef Plass C, Adebar N, Hiessl R, Kleber J, Grimm A, Langsch A, Otter R, Liese A, Gröger H (2021) Structure-performance guided design of sustainable plasticizers from Biorenewable Feedstocks. Eur J Org Chem 2021:6086–6096CrossRef
17.
go back to reference Kumar S (2019) Recent developments of biobased plasticizers and their effect on mechanical and thermal properties of poly(vinyl chloride): a review. Ind Eng Chem Res 58:11659–11672CrossRef Kumar S (2019) Recent developments of biobased plasticizers and their effect on mechanical and thermal properties of poly(vinyl chloride): a review. Ind Eng Chem Res 58:11659–11672CrossRef
18.
go back to reference Hao YY, Tian AP, Zhu J, Fan JS, Yang Y (2020) Synthesis and evaluation of Bio-based plasticizers from 5-Hydroxymethyl-2-Furancarboxylic acid for poly(vinyl chloride. Ind Eng Chem Res 59:18290–18297CrossRef Hao YY, Tian AP, Zhu J, Fan JS, Yang Y (2020) Synthesis and evaluation of Bio-based plasticizers from 5-Hydroxymethyl-2-Furancarboxylic acid for poly(vinyl chloride. Ind Eng Chem Res 59:18290–18297CrossRef
19.
go back to reference Hao YY, Wang GY, Shui XX, Tian AP, Yang Y, Zhu J (2021) Design and synthesis of HFCA-based plasticizers with asymmetrical alkyl chains for poly(vinyl chloride). J Appl Polym Sci 138:e51410CrossRef Hao YY, Wang GY, Shui XX, Tian AP, Yang Y, Zhu J (2021) Design and synthesis of HFCA-based plasticizers with asymmetrical alkyl chains for poly(vinyl chloride). J Appl Polym Sci 138:e51410CrossRef
20.
go back to reference Liang XJ, Wu FJ, Xie QL, Wu ZY, Cai JJ, Zheng CW, Fu JH, Nie Y (2021) Insights into biobased epoxidized fatty acid isobutyl esters from biodiesel: Preparation and application as plasticizer. Chin J Chem Eng 44:41–50CrossRef Liang XJ, Wu FJ, Xie QL, Wu ZY, Cai JJ, Zheng CW, Fu JH, Nie Y (2021) Insights into biobased epoxidized fatty acid isobutyl esters from biodiesel: Preparation and application as plasticizer. Chin J Chem Eng 44:41–50CrossRef
21.
go back to reference Chaochanchaikul K, Pongmuksuwan P (2021) Infuence of ozonized soybean oil as a biobased plasticizer on the toughness of polylactic acid. J Polym Environ 30:1095–1105CrossRef Chaochanchaikul K, Pongmuksuwan P (2021) Infuence of ozonized soybean oil as a biobased plasticizer on the toughness of polylactic acid. J Polym Environ 30:1095–1105CrossRef
22.
go back to reference Gama N, Santos R, Godinho B, Silva R, Ferreira A (2019) Triacetin as a secondary PVC Plasticizer. J Polym Environ 27:1294–1301CrossRef Gama N, Santos R, Godinho B, Silva R, Ferreira A (2019) Triacetin as a secondary PVC Plasticizer. J Polym Environ 27:1294–1301CrossRef
23.
go back to reference Yang D, Peng XW, Zhong LX, Cao XF, Chen W, Zhang XM, Liu SJ, Sun RC (2014) Green films from renewable resources: Properties of epoxidized soybean oil plasticized ethyl cellulose films. Carbohydr Polym 103:198–206PubMedCrossRef Yang D, Peng XW, Zhong LX, Cao XF, Chen W, Zhang XM, Liu SJ, Sun RC (2014) Green films from renewable resources: Properties of epoxidized soybean oil plasticized ethyl cellulose films. Carbohydr Polym 103:198–206PubMedCrossRef
24.
go back to reference Nihul PG, Mhaske ST, Shertukde VV (2014) Epoxidized rice bran oil (ERBO) as a plasticizer for poly(vinyl chloride) (PVC). Iran Polym J 23:599–608CrossRef Nihul PG, Mhaske ST, Shertukde VV (2014) Epoxidized rice bran oil (ERBO) as a plasticizer for poly(vinyl chloride) (PVC). Iran Polym J 23:599–608CrossRef
25.
go back to reference Chen J, Liu ZS, Li K, Huang JR, Nie XA, Zhou YH (2015) Synthesis and application of a natural plasticizer based on cardanol for poly(vinyl chloride). J Appl Polym Sci 132:42465CrossRef Chen J, Liu ZS, Li K, Huang JR, Nie XA, Zhou YH (2015) Synthesis and application of a natural plasticizer based on cardanol for poly(vinyl chloride). J Appl Polym Sci 132:42465CrossRef
26.
go back to reference Chen J, Liu ZS, Li XY, Liu P, Jiang JC, Nie XA (2016) Thermal behavior of epoxidized cardanol diethyl phosphate as novel renewable plasticizer for poly(vinyl chloride). Polym Degrad Stab 126:58–64CrossRef Chen J, Liu ZS, Li XY, Liu P, Jiang JC, Nie XA (2016) Thermal behavior of epoxidized cardanol diethyl phosphate as novel renewable plasticizer for poly(vinyl chloride). Polym Degrad Stab 126:58–64CrossRef
27.
go back to reference Chen J, Liu ZS, Jiang JC, Nie XA, Zhou YH, Murray RE (2015) A novel biobased plasticizer of epoxidized cardanol glycidyl ether: synthesis and application in soft poly(vinyl chloride). Films RSC Adv 5:56171–56180CrossRef Chen J, Liu ZS, Jiang JC, Nie XA, Zhou YH, Murray RE (2015) A novel biobased plasticizer of epoxidized cardanol glycidyl ether: synthesis and application in soft poly(vinyl chloride). Films RSC Adv 5:56171–56180CrossRef
28.
go back to reference Satavalekar SD, Savvashe PB, Mhaske ST (2016) Triester-amide based on thiophene and ricinoleic acid as an innovative primary plasticizer for poly(vinyl chloride). RSC Adv 6:115101–115112CrossRef Satavalekar SD, Savvashe PB, Mhaske ST (2016) Triester-amide based on thiophene and ricinoleic acid as an innovative primary plasticizer for poly(vinyl chloride). RSC Adv 6:115101–115112CrossRef
29.
go back to reference Maiza M, Benaniba MT, Massardier-Nageotte V (2016) Plasticizing effects of citrate esters on properties of poly(lactic acid). J Polym Eng 36:371–380CrossRef Maiza M, Benaniba MT, Massardier-Nageotte V (2016) Plasticizing effects of citrate esters on properties of poly(lactic acid). J Polym Eng 36:371–380CrossRef
30.
go back to reference Kim H, Ji YS, Rehman SU, Choi MS, Gye MC, Yoo HH (2019) Pharmacokinetics and metabolism of acetyl triethyl citrate, a water-soluble plasticizer for pharmaceutical polymers in rats. Pharmaceutics 11:162PubMedPubMedCentralCrossRef Kim H, Ji YS, Rehman SU, Choi MS, Gye MC, Yoo HH (2019) Pharmacokinetics and metabolism of acetyl triethyl citrate, a water-soluble plasticizer for pharmaceutical polymers in rats. Pharmaceutics 11:162PubMedPubMedCentralCrossRef
31.
go back to reference Liu JY, Yuan R, Sang Q, Dang L, Gao L, Xu BH, Xu SI (2022) Effect of acetylated citrate plasticizer on mechanical properties of poly (vinyl chloride). Mater Chem Phys 295:127068CrossRef Liu JY, Yuan R, Sang Q, Dang L, Gao L, Xu BH, Xu SI (2022) Effect of acetylated citrate plasticizer on mechanical properties of poly (vinyl chloride). Mater Chem Phys 295:127068CrossRef
32.
go back to reference Harte I, Birkinshaw C, Jones E, Kennedy J, DeBarra E (2013) The effect of citrate ester plasticizers on the thermal and mechanical properties of poly(DL-lactide). J Appl Polym Sci 127:1997–2003CrossRef Harte I, Birkinshaw C, Jones E, Kennedy J, DeBarra E (2013) The effect of citrate ester plasticizers on the thermal and mechanical properties of poly(DL-lactide). J Appl Polym Sci 127:1997–2003CrossRef
33.
go back to reference Tsou CH, Suen MC, Yao WH, Yeh JT, Wu CS, Tsou CY, Chiu SH, Chen JC, Wang RY, Lin SM, Hung WS, De Guzman M, Hu CC, Lee KR (2014) Preparation and characterization of bioplastic-based green renewable composites from tapioca with acetyl tributyl citrate as a plasticizer. Materials 7:5617–5632PubMedPubMedCentralCrossRef Tsou CH, Suen MC, Yao WH, Yeh JT, Wu CS, Tsou CY, Chiu SH, Chen JC, Wang RY, Lin SM, Hung WS, De Guzman M, Hu CC, Lee KR (2014) Preparation and characterization of bioplastic-based green renewable composites from tapioca with acetyl tributyl citrate as a plasticizer. Materials 7:5617–5632PubMedPubMedCentralCrossRef
34.
go back to reference Yin B, Hakkarainen M (2011) Oligomeric Isosorbide Esters as alternative renewable resource plasticizers for PVC. J Appl Polym Sci 119:2400–2407CrossRef Yin B, Hakkarainen M (2011) Oligomeric Isosorbide Esters as alternative renewable resource plasticizers for PVC. J Appl Polym Sci 119:2400–2407CrossRef
35.
go back to reference Adhikari B, Chaudhary DS, Clerfeuille E (2010) Effect of plasticizers on the moisture migration behavior of low-amylose starch films during drying. Dry Technol 28:468–480CrossRef Adhikari B, Chaudhary DS, Clerfeuille E (2010) Effect of plasticizers on the moisture migration behavior of low-amylose starch films during drying. Dry Technol 28:468–480CrossRef
36.
go back to reference Hou BY, Ren L, Fu DM, Jiang YY, Zhang MY, Zhang HX (2021) Novel environmentally sustainable xylitolbased plasticizer: synthesis and application. J Polym Res 28:337CrossRef Hou BY, Ren L, Fu DM, Jiang YY, Zhang MY, Zhang HX (2021) Novel environmentally sustainable xylitolbased plasticizer: synthesis and application. J Polym Res 28:337CrossRef
37.
go back to reference Zdanowicz M, Staciwa P, Spychaj T (2019) Low transition temperature mixtures (LTTM) containing sugars as Potato Starch plasticizers. Starch-Starke 71:1900004CrossRef Zdanowicz M, Staciwa P, Spychaj T (2019) Low transition temperature mixtures (LTTM) containing sugars as Potato Starch plasticizers. Starch-Starke 71:1900004CrossRef
40.
go back to reference Yang Y, Huang JC, Zhang RY, Zhu J (2017) Designing bio-based plasticizers: effect of alkyl chain length on plasticization properties of isosorbide diesters in PVC blends. Mater Des 126:29–36CrossRef Yang Y, Huang JC, Zhang RY, Zhu J (2017) Designing bio-based plasticizers: effect of alkyl chain length on plasticization properties of isosorbide diesters in PVC blends. Mater Des 126:29–36CrossRef
41.
go back to reference Yang Y, Xiong Z, Zhang LS, Tang ZB, Zhang RY, Zhu J (2016) Isosorbide dioctoate as a green plasticizer for poly(lactic acid). Mater Des 91:262–268CrossRef Yang Y, Xiong Z, Zhang LS, Tang ZB, Zhang RY, Zhu J (2016) Isosorbide dioctoate as a green plasticizer for poly(lactic acid). Mater Des 91:262–268CrossRef
42.
go back to reference Yang Y, Xiong Z, Zhang LS, Tang ZB, Zhang RY, Zhu J (2016) Effect of isosorbol-based plasticizers on thermal, mechanical properties and crystalline behavior of PLA. Plast Addit 3:57–62 Yang Y, Xiong Z, Zhang LS, Tang ZB, Zhang RY, Zhu J (2016) Effect of isosorbol-based plasticizers on thermal, mechanical properties and crystalline behavior of PLA. Plast Addit 3:57–62
43.
go back to reference Jiang YY, Ren L, Wu GH, Guo W, Guan XF, Zhang MY, Zhang HX (2022) An environmentally sustainable isosorbide-based plasticizer for biodegradable poly(butylene succinate). J Polym Eng 42:331–342CrossRef Jiang YY, Ren L, Wu GH, Guo W, Guan XF, Zhang MY, Zhang HX (2022) An environmentally sustainable isosorbide-based plasticizer for biodegradable poly(butylene succinate). J Polym Eng 42:331–342CrossRef
44.
go back to reference Li WB, Ren L, Tao ZJ, Shuai JX, Ma H, Zhao HM (2021) The design and preparation of isosorbide-based plasticizer and its application in poly(vinyl chloride). Eng Plast Appl 49:123–126 Li WB, Ren L, Tao ZJ, Shuai JX, Ma H, Zhao HM (2021) The design and preparation of isosorbide-based plasticizer and its application in poly(vinyl chloride). Eng Plast Appl 49:123–126
45.
go back to reference Kirkpatrick A (1940) Some relations between molecular structure and plasticizing effect. J Appl Phys 11:255–261CrossRef Kirkpatrick A (1940) Some relations between molecular structure and plasticizing effect. J Appl Phys 11:255–261CrossRef
46.
go back to reference Flory TGF Jr (1950) Second-order transition temperatures and related properties of polystyrene.I. Influence of molecular weight. J Appl Phys 21:581–591CrossRef Flory TGF Jr (1950) Second-order transition temperatures and related properties of polystyrene.I. Influence of molecular weight. J Appl Phys 21:581–591CrossRef
47.
go back to reference Zhang KX, Du J, Du GF (2014) Material synthesis and preparation research. China Water & Power Press, Beijing Zhang KX, Du J, Du GF (2014) Material synthesis and preparation research. China Water & Power Press, Beijing
Metadata
Title
An eco-friendly sustainable plasticizer from isosorbide and nonanoic acid: synthesis and application
Authors
T. Song
L. Ren
W. B. Li
Q. Liu
Y. X. Qin
Y. L. Zhang
Y. B. Wang
Y. D. Shen
W. N. Du
M. Y. Zhang
Publication date
01-01-2024
Publisher
Springer Netherlands
Published in
Journal of Polymer Research / Issue 1/2024
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-023-03837-w

Other articles of this Issue 1/2024

Journal of Polymer Research 1/2024 Go to the issue

Premium Partners