Skip to main content
SpringerLink
Log in

Cross-Linking Agents

  • Living reference work entry
  • Latest version View entry history
  • First Online:
Polymers and Polymeric Composites: A Reference Series

Part of the book series: Polymers and Polymeric Composites: A Reference Series ((POPOC))

  • 192 Accesses

Abstract

A cross-linking agent is one of the important additives in the plastic industry. Cross-linking agents have an effect on the physical and mechanical properties of the polymers. In general, the curing or cross-linking process is an irreversible process. The cross-linking of polymer which is done by cross-linkers through covalent bond enables to control the physical and mechanical (i.e., impact and resistance of cracking) properties of the obtained polymer for commercial or scientific purposes. At the beginning of the entry, some important definitions as cross-link and cross-linking density were summarized. The types of cross-linking agents were discussed in detail in the entry. Then, some interesting items were discussed as there are cross-linking agents utilized in the plastic industry without external stimuli and others that need external stimuli (i.e., thermal or photo-irradiation, etc.), the latter of which are called latent curing agents. The common latent cross-linking agents based on imidazole are mentioned, and its working mechanism in the curing process is shown in the entry. The selection of the appropriate cross-linker was mentioned through discussion of the cross-linking agents based on the functional groups present on the polymer such as amine or anhydride groups. Consequently, the illustration of the function group should be present on the polymer needed to cure. For example, cross-linking agents based on polyamines were utilized with polymers that have epoxide, thiirane or methylene chloride, or ketone groups. The former cross-linking based on compounds have amino, the working mechanisms of each cross-linking agent were illustrated in detail. At the end of entries, cross-linking of important daily used plastic by different cross-linking agents was discussed such as polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), polyurethane (PU), and polyepoxide (epoxy).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

References

  • Amariutei OA, Ramsdale-Capper R, Álvarez MC, Chan LKY, Foreman JP (2018) Modelling the properties of a difunctional epoxy resin cured with aromatic diamine isomers. Polymer 156(7):203–213

    Article  CAS  Google Scholar 

  • Anbarasan R, Babot O, Maillard B (2004) Cross-linking of high-density polyethylene in the presence of organic peroxides. J Appl Polym Sci 93:75–81

    Article  CAS  Google Scholar 

  • Arimitsu K, Fuse S, Kudo K, Furutani M (2015) Imidazole derivatives as latent curing agents for epoxy thermosetting resins. Mater Lett 161:408–410

    Article  CAS  Google Scholar 

  • Atta AM (2003) Epoxy resin based on poly(ethylene terephthalate) waste: synthesis and characterization. Prog Rubber Plast Recycl Technol 19(1):17–40

    Article  CAS  Google Scholar 

  • Biju R, Nair CPR (2013) Synthesis and characterization of shape memory epoxy-an hydride system. J Polym Res 20:82–92

    Article  CAS  Google Scholar 

  • Chaudhary BI, Sengupta SS, Cogen JM, Curto M (2011) Silane grafting and moisture cross-linking of polypropylene. Polym Eng Sci 51(2):237–246

    Article  CAS  Google Scholar 

  • Chino K, Suga K, Ikawa M, Satoh H (2001) Novel rapid-cure adhesives for low temperature using Thiirane compound. J Appl Polym Sci 82:2953–2957

    Article  CAS  Google Scholar 

  • Chiu Y-C, Huang C-C, Tsai H-C, Prasannan A, Toyoko I (2013) Effect of aromatic and aliphatic amines as curing agents in sulfone epoxy monomer curing process. Polym Bull 70:1367–1382

    Article  CAS  Google Scholar 

  • Chodák I (1999) Chapter. Cross-linking of polypropylene. In: Polypropylene, volume 2 of the series. Polymer science and technology series. Springer, Dordrecht, pp 128–134

    Google Scholar 

  • Choi HK, Choi BG, Lee YY, Na JS (2015) Cationic catalyst as latent curing agent for epoxy resin. Appl Mech Mater 749:126–128

    Article  Google Scholar 

  • Chung Y-C, Choi JW, Moon S, Chun BC (2009) Effect of cross-linking agent structure on the shape memory property of polyurethane block copolymer. Fiber Polym 10(4):430–436

    Article  CAS  Google Scholar 

  • Costa ML, Pardini LC, Rezende MC (2005) Influence of aromatic amine hardeners in the cure kinetics of an epoxy resin used in advanced composites. Mater Res 8(1):65–70

    Article  CAS  Google Scholar 

  • Fedoseev MS, Derzhavinskaya LF, Valeev NS, Chulanova SN, Yampol’skaya VD (2008) Curing of epoxy oligomers by the eutectic mixture of aromatic amines. Polym Sci Ser D Glues Sealing Mater 1(1):41–43

    Article  Google Scholar 

  • Fedoseev MS, Derzhavinskaya LF, Strel’nikov VN (2010) Curing of epoxy-anhydride formulations in the presence of imidazoles. Russ J Appl Chem 83(8):1408–1412

    Article  CAS  Google Scholar 

  • Fedoseev MS, Gruzdev MS, Derzhavinskaya LF (2014) 1-Butyl-3-methylimidazolium salts as new catalysts to produce epoxy-anhydride polymers with improved properties. Int J Polym Sci 2014:Article ID 607341, 8 pages

    Article  CAS  Google Scholar 

  • Ferdosian F, Yuan Z, Anderson M, (Charles) Xu C (2015) Sustainable lignin-based epoxy resins cured with aromatic and aliphatic amine curing agents: Curing kinetics and thermal properties. Thermochim Acta 618:48–55

    Article  CAS  Google Scholar 

  • Fraga F, Vazquez EC, Rodríguez-Núñez E, Martínez-Ageitos JM (2008) Curing kinetics of the epoxy system diglycidyl ether of bisphenol A/isophoronediamine by Fourier transform infrared spectroscopy. Polym Adv Technol 19, 1623–1628

    Google Scholar 

  • Francis B, Rao VL, Jose S, Catherine BK, Ramaswamy R, Jose J, Thoma S (2006) Poly(ether ether ketone) with pendent methyl groups as a toughening agent for amine cured DGEBA epoxy resin. J Mater Sci 41:5467–5479

    Article  CAS  Google Scholar 

  • García L, Morales G, Avalos BF, Acunã P (2013) Use of the trifunctional cyclic initiator, DEKTP, as the radical initiator in the modification of poly(propylene) in the presence of different branching/cross-linking co-agents. Macromol Symp 325–326:213–219

    Article  CAS  Google Scholar 

  • García-Quesada JC, Marcilla A, Gilbert M (2001) Thermal degradation of silane crosslinked unplasticized PVC. J Anal Appl Pyrolysis 60(2):159–177

    Article  Google Scholar 

  • Ghasemi I, Morshedian J (2003) The effect of co-agent on the peroxide cross-linking of LDPE. Iran Polym J 12(2):119–125

    CAS  Google Scholar 

  • Gilbert M, Garci’a-Quesada JC (1999) Cross-linking of rigid poly(vinyl chloride). Plast Rubber Compos 28(3):125–130

    Article  CAS  Google Scholar 

  • Gilbert MD, Schneider NS, MacKnight WJ (1991) Mechanism of the dicyandiamide/epoxide reaction. Macromolecules 24(2):360–369

    Article  CAS  Google Scholar 

  • González MG, Cabanelas JC, Pozuelo J, Baselga J (2011) Preparation of cycloaliphatic epoxy hybrids with non-conventional amine-curing agents. J Therm Anal Calorim 103(2):717–723

    Article  CAS  Google Scholar 

  • Gooch JW (2011) Polyurethane. In: Gooch JW (ed) Encyclopedic dictionary of polymers. Springer, New York

    Chapter  Google Scholar 

  • Gunewardena A, Gilbert M (2008) Peroxide cross-linking of rigid poly(vinyl chloride). J Vinyl Addit Technol 14(3):92–98

    Article  CAS  Google Scholar 

  • Ham YR, Kim SH, Shin YJ, Lee DH, Yang M, Min JH, Shin JS (2010) A comparison of some imidazoles in the curing of epoxy resin. J Ind Eng Chem 16(4):556–559

    Article  CAS  Google Scholar 

  • Hara O (1990) Curing agents for epoxy resin. Three Bond Technical News Issued

    Google Scholar 

  • Hartshorn SJ (1986) Durability of adhesive joints in structural adhesives. Plenum Press, New York, ISBN 978-1-4684-7781-8

    Google Scholar 

  • Kelnar I, Schatz M (1993) Silane cross-linking of PVC. II. Influence of silane type and conditions on cross-linking by water. J Appl Polym Sci 48:669–676

    Article  CAS  Google Scholar 

  • Kim TH, Kim DY, Lim CS, Seo BK (2017) Studies of the physical properties of cycloaliphatic epoxy resin reacted with anhydride curing agents. Key Eng Mater 737:248–255

    Article  Google Scholar 

  • Kolář F, Svítilová J (2007) Kinetics and mechanism of curing epoxy/anhydride systems. Acta Geodyn Geomater 4(3)(147):85–92

    Google Scholar 

  • Kudo K, Furutani M, Arimitsu K (2015) Imidazole derivatives with an intramolecular hydrogen bond as thermal latent curing agents for thermosetting resins ACS. Macro Lett 4(10):1085–1088

    Article  CAS  Google Scholar 

  • Kumar A, Ujjwal RR, Mittal A, Bansal A, Ojha U (2014) Polyacryloyl hydrazide: an efficient, simple, and cost effective precursor to a range of functional materials through hydrazide based click reactions. ACS Appl Mater Interfaces 6(3):1855–1865

    Article  CAS  PubMed  Google Scholar 

  • Lendlein A, Kelch S (2002) Shape memory polymers. Angew Chem Int Ed 41:2034–2057

    Article  CAS  Google Scholar 

  • Li L, Chen X, He B (2007) Cross-linking of rigid poly(vinyl chloride) with epoxysilane. J Vinyl Addit Technol 13(2):103–109

    Article  CAS  Google Scholar 

  • Li J, Wang B, Chen K, Tian X, Zeng J, Xu J, Gao W (2017) The use of lignin as cross-linker for polyurethane foam for potential application in adsorbing materials. BioRes 12(4):8653–8671

    CAS  Google Scholar 

  • Liu H, Chuai C, Iqbal M, Wang H, Kalsoom BB, Khattak M, Khattak MQ (2011) Improving foam ability of polypropylene by cross-linking. J Appl Polym Sci 122:973–980

    Article  CAS  Google Scholar 

  • López-Barajas F, Ramos-DeValle LF, Sánchez-Valdes S, Ramírez-Vargas E, Martínez-Colunga G, Espinoza-Martínez AB, Flores-Gallardo S, Mendez-Nonell J, Morales-Cepeda AB, Lozano-Ramirez T, Beltrán-Ramírez FI (2019) Curing kinetics of diglycidyl ether of bisphenol-A epoxy system using a tertiary amine, through the study of its rheometric characteristics. Polym Test 73:346–351

    Article  CAS  Google Scholar 

  • Luo Y, Zou J, Li J, Zou H, Liang M (2018) Effect of crosslinking agent on properties and morphology of water-blown semirigid polyurethane foam. J Appl Polym Sci 135(42):1953–1959

    Article  CAS  Google Scholar 

  • Mallick PK (1997) Composites engineering handbook. Marcel Dekker, New York, p 121

    Book  Google Scholar 

  • Massingill JL, Bauer RS (2000) Epoxy Resins. Applied Polymer Science: 21st Century, Pergamon, 393–424, ISBN 9780080434179

    Google Scholar 

  • Meloa RP, Aguiara VO, Marques MFV (2015) Silane crosslinked polyethylene from different commercial PE’s: influence of comonomer, catalyst type and evaluation of HLPB as cross-linking coagent. Mater Res 18(2):313–319

    Article  CAS  Google Scholar 

  • Miller (1995) Introduction to plastics and composites: mechanical properties and engineering applications. Volume 101 of Mechanical engineering. Marcel Dekker, INC. New York: CRC Press, pp 122–143

    Google Scholar 

  • Minsker KS, Kolesov SV, Zaikov GE (1995) Degradation and stabilization of vinyl chloride-based polymers. Pergamon, Oxford, p 76, 1998.

    Google Scholar 

  • Mori A, Kitayama T, Takatani M, Okamoto T (2004) A honeymoon-type adhesive for wood products based on acetoacetylated poly(vinyl alcohol) and diamines: effect of diamines and degree of acetoacetylation. J Appl Polym Sci 91:2966–2972

    Article  CAS  Google Scholar 

  • Nikolic G, Zlatkovic S, Cakic M, Cakic S, Lacnjevac C, Rajic Z (2010) Fast Fourier transform IR characterization of epoxy GY systems crosslinked with aliphatic and cycloaliphatic EH polyamine adducts. Sensors 10:684–696

    Article  CAS  PubMed  Google Scholar 

  • Paulmer RDA, Shah CS, Patni MJ, Pandya MV (1991) Effect of crosslinking agents on the structure and properties of polyurethane millable elastomer composites. J Appl Polym Sci 43, 1953–1959

    Google Scholar 

  • Petrie EM (2006) Epoxy adhesive formulations. McGraw-Hill chemical engineering. McGraw-Hill, New York, p 62

    Google Scholar 

  • Ray P (2011) Polymer cross-linkling. In: Encyclopedia of polymer science and technology. https://doi.org/10.1002/0471440264.pst400

    Chapter  Google Scholar 

  • Rocks J, George GA, Vohwinkel F (2003) Curing kinetics and thermomechanical behaviour of co-anhydride cured aminoglycidyl epoxy resins. Polym Int 52:1758–1766

    Article  CAS  Google Scholar 

  • Saethre B, Gilbert M (1996) Peroxide cross-linking of plasticized poly(vinyl chloride). Polymer 37(15):3379–3386

    Article  CAS  Google Scholar 

  • Song G, Yang S, Yang C, She X (2006) Foaming polypropylene prepared by a novel one-step silane-grafting and cross-linking method. J Porous Mater 13:297–301

    Article  CAS  Google Scholar 

  • Su WF, Huang HW, Pan WP (2002a) Thermal properties of rigid rod epoxies cured with diaminodiphenylsulfone and dicyandiamide. Thermochim Acta 392–393:391–394

    Article  Google Scholar 

  • Su WF, Lee YC, Pan WP (2002b) Thermal properties of phthalic anhydride- and phenolic resin-cured rigid rod epoxy resins. Thermochim Acta 392–393:395–398

    Article  Google Scholar 

  • Suyama S, Ishigaki H, Watanabe Y, Nakamura T (1995) Cross-linking of polyethylene by dicumyl peroxide in the presence of 2,4-diphenyl-4-methyl-1-pentene. Polym J 27(4):371–375

    Article  CAS  Google Scholar 

  • Tamboli SM, Mhaske ST, kale DD (2004) Cross-linking polyethylene. IJCT 11:853–864

    CAS  Google Scholar 

  • Thomas NL, Zheng X (2007) Peroxide cross-linking of rigid poly(vinyl chloride). J Appl Polym Sci 103(5):2904–2909

    Article  CAS  Google Scholar 

  • Tomuta AM, Ramis X, Ferrando F, Serra A (2012) The use of dihydrazides as latent curing agents in diglycidyl ether of bisphenol-A coatings. Prog Org Coat 74:59–66

    Article  CAS  Google Scholar 

  • Tötsch W, Gaensslen H (1992) Poly (vinylchloride): environmental aspects of a common plastic. Elsevier Applied Science, London/New York. ISBN 1-85166-774-1

    Google Scholar 

  • Varma IK, Gupta VB (2000) 2.01 – Thermosetting Resin–Properties. Comprehensive Composite Materials, Pergamon, 1–56, ISBN 9780080429939

    Google Scholar 

  • Wang J, Xu YZ, Fu YF, Liu XD (2016) Latent curing systems stabilized by reaction equilibrium in homogeneous mixtures of benzoxazine and amine. Sci Rep 6:Article number: 38584

    Article  PubMed Central  CAS  Google Scholar 

  • Wang Y, Liu W, Qiu Y, Wei Y (2018) A one-component, fast-cure, and economical epoxy resin system suitable for liquid molding of automotive composite parts. Materials (Basel) 11(5):685–696

    Article  PubMed Central  CAS  Google Scholar 

  • Wlodarska M, Maj A, Mossety-Leszczak B, Bak GW, Galina H, Okrasa L, Izdebski M (2013) Liquid crystal epoxy resins based on biphenyl group cured with aromatic amines – studied by dielectric spectroscopy. J Polym Res 20:227–234

    Article  CAS  Google Scholar 

  • Wu F, Zhou X, Yu X (2018) Reaction mechanism, cure behavior and properties of a multifunctional epoxy resin, TGDDM, with latent curing agent dicyandiamide. RSC Adv 8:8248–8258

    Article  CAS  Google Scholar 

  • Xie M, Zhang Z, Gu Y, Li M, Su Y (2009) A new method to characterize the cure state of epoxy prepreg by dynamic mechanical analysis. Thermochim Acta 487:8–17

    Article  CAS  Google Scholar 

  • Xiong C, Yao C (2009) Synthesis, characterization and application of triethylenetetramine modified polystyrene resin in removal of mercury, cadmium and lead from aqueous solutions. Chem Eng J 155:844–850

    Article  CAS  Google Scholar 

  • Yadav RP, Gope PC, Sah PL (2007) Mechanical and thermal properties of acrylic hydrazide cured epoxy; in-situ polymerization experimental analysis of nano and engineering materials and structures. Springer: Springer Netherlands. Print ISBN: 978-1-4020-6238-4. Electronic ISBN: 978-1-4020-6239-1

    Google Scholar 

  • Yang B, Mao Y, Zhang Y, Bian G, Zhang L, Wei Y, Jiang Q, Qiu Y, Liu W (2019) A novel liquid imidazole-copper (II) complex as a thermal latent curing agent for epoxy resins. Polymer 178:121586

    Article  CAS  Google Scholar 

  • Yin GT, Rong MZ, Zhang MQ, Yang GC (2007) Self-healing epoxy composites – preparation and effect of the healant consisting of microencapsulated epoxy and latent curing agent. Compos Sci Technol 67(2):201–212

    Article  CAS  Google Scholar 

  • Yu Q, Zhu S (1999) Peroxide cross-linking of isotactic and syndiotactic polypropylene. Polymer 40(11):2961–2968

    Google Scholar 

  • Zadhoush A, Esmaeili M, Ghaeli I (2009) Cross-linking of plasticized PVC used in coated fabrics. J Vinyl Addit Technol 15(2):108–112

    CAS  Google Scholar 

  • Zhang C, Liu X, Cheng J, Zhang J (2015) Study on curing kinetics of diglycidyl 1,2-cyclohexane dicarboxylate epoxy/episulfide resin system with hexahydro-4-methylphthalic anhydride as a curing agent. J Therm Anal Calorim 120(3):1893–1903

    Article  CAS  Google Scholar 

  • Zhou S, Hu M, Hu Y, Wang Z (2009) Influence of coagents on the silane grafting and cross-linking of polypropylene. Polym Plast Technol Eng 48(2):193–200

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt

    Soliman Mehawed Abdellatif Soliman

Authors
  1. Soliman Mehawed Abdellatif Soliman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Soliman Mehawed Abdellatif Soliman .

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer-Verlag GmbH Germany, part of Springer Nature

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Soliman, S.M.A. (2020). Cross-Linking Agents. In: Polymers and Polymeric Composites: A Reference Series. Polymers and Polymeric Composites: A Reference Series. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-37179-0_82-2

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-37179-0_82-2

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-37179-0

  • Online ISBN: 978-3-642-37179-0

  • eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

Publish with us

Policies and ethics

Chapter history

  1. Latest

    Cross-Linking Agents
    Published:
    05 June 2020

    DOI: https://doi.org/10.1007/978-3-642-37179-0_82-2

  2. Original

    Cross-Linking Agents
    Published:
    13 November 2019

    DOI: https://doi.org/10.1007/978-3-642-37179-0_82-1

Search

Navigation