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Chemistry Africa

, Volume 2, Issue 2, pp 215–221 | Cite as

1,3-Propanediol and its Application in Bio-Based Polyesters for Resin Applications

  • Marcel Kluge
  • Sacha Pérocheau Arnaud
  • Tobias RobertEmail author
Invited Review

Abstract

Polyester resins are important raw materials for a myriad of applications especially in the field of coatings and radical curing polymers, such as wood and powder coatings, molding compounds, and UV-curing applications. In addition, polyols derived from polyester resins are precursors for the synthesis of polyurethanes and polycarbonates. Besides dicarboxylic acid, diols are used as monomers in these polyesters. To date most of the diols utilized are derived from petrochemical feedstock. To increase the bio-based content of polyester resins, novel diols derived from renewable resources are of special interest. In this respect, 1,3-propanediol has drawn considerable attention over the last years. It is accessible via microbial fermentation of glucose from starch at a competitive price in sufficient amounts. Therefore, 1,3-propanediol could be a valuable alternative to petrochemical diols, such as 1,6-hexanediol and neopentylglycol, which are currently used as diols in most resin applications. This article gives a brief overview over the utilization of 1,3-propanediol in high molecular weight polyesters for plastic application followed by a more detailed discussion of the most relevant work in the field of polyester resins derived from 1,3-propanediol.

Keywords

1,3-Propanediol Polyester resins Coatings Unsaturated polyesters 

1 Introduction

The last decade has seen a growing interest in bio-based materials. Especially in the polymer field, the demand for alternatives from renewable resources is continuously increasing. This trend is driven by the finite nature of fossils fuels, but also a rising consumer awareness and lately the problem of rising accumulation of (micro) plastic in the environment, in particular in the oceans. The latter results in an increasing attention towards the transition to a circular economy and the development of bio-degradable plastics [1]. Against this background, bio-based polyesters are of special significance [2]. They are derived from renewable resources and exhibit in many cases a higher bio-degradability in comparison to other bio-based plastics, such as bio-polyethylene. The most prominent examples in the field of bio-based polyesters are polylactic acid (PLA) [3, 4, 5] and polyhydroxyalkanoates (PHA) [4, 6, 7, 8, 9], which are both commercially available. Especially PLA is employed in a variety of applications, such as packaging, composite materials and biomedical applications [5, 10, 11, 12, 13, 14].

In addition, other bio-based polyesters have been in the focus of both academic as well as industrial research and are in different stages of commercial availability. A range of bio-sourced monomers, such as furandicarboxylic acid (FDCA), succinic acid, isosorbide, etc. have been used and there are a range of extensive book chapters and review articles that cover this topic of polymer and material science [15, 16, 17, 18, 19, 20, 21, 22]. Among these building blocks, 1,3-propanediol (PDO) has been successfully applied in a several bio-based polyesters.

Even though this diol is accessible by synthetic pathways, for example from acrolein [23] or ethylene oxide [24] these methods suffer from high production costs and undesired and irritant impurities. This led to low interest in this monomer from an industrial viewpoint and therefore very limited applications. However, the situation changed when PDO was made accessible through microbial fermentation of glucose [25, 26]. This biotechnological pathway led to an increased availability of PDO at a competitive price and in turn to more applications of this bio-based building block in polymer materials.

As most promising examples, PDO was used as monomer for the bio-based PET alternatives PTT (poly(trimethylene terephthalate)) [27, 28, 29] and PTF (poly(trimethylenefuroate)) [30, 31, 32] (Fig. 1a). In comparison to PET, PTT shows high resilience and has the ability to rapidly crystallize, which makes it a promising candidate for fiber applications [33]. PTF on the other hand shows superior gas barrier properties than the (partially) petrochemical polymers PET and PTT [34]. As another example in the field of bio-based polyesters with aromatic building blocks, PDO was utilized as diol component with the difuranic monomer 5,5′-(propane-2,2-diyl)-bis(furan-2-carboxylate) [35].
Fig. 1

Chemical structure of a aromatic and b aliphatic polyesters with PDO

In addition, a lot of work was dedicated towards aliphatic polyesters derived from PDO (Fig. 1b) [36, 37, 38, 39]. These polyesters are especially interesting due to their high susceptibility towards enzymatic degradation [37, 40]. This makes these polymers promising candidates for degradable plastics, as well as pharmaceutical applications.

Both the aromatic, as well as aliphatic polyesters derived from PDO have been studied extensively and are the subject of several comprehensive review articles [22, 41, 42, 43, 44, 45]. PDO has also been used as monomer for polyester resins in the coatings field. To the best of our knowledge, no review for this type of polyesters derived from PDO for binder resins has been made. Herein, we try to give an overview of the most important work undertaken in this area in the last years.

2 Polyester Resins from 1,3-Propandiol

2.1 Polyester Polyols for Polyurethanes and Polycarbonates

In 2001 Albertsson and co-workers reported the synthesis of different bio-based poly(1,3-propylene succinate) oligomers, by varying the diol/diacid ratio from 1.05 to 1.25 (Scheme 1a) [46]. This led to polyesters with different properties and low molecular weights up to 3400 g/mol. These oligomers were further reacted with methylenediphenylisocyanate (MDI) to obtain polyester urethanes with molecular weights up to 60,000 g/mol. The properties of these polymers were examined in the dependency of the weight percentage of the polyester polyol incorporated. The melting point varied in the range of 175–210 °C with properties comparable to commercial thermoplastic polyurethanes.
Scheme 1

Bio-based poly(1,3-propylene succinate) as precursor for polyurethanes and polycarbonates through a reaction with a MDI and b phosgene, dimethylamino pyridine (DMAP) and a tertiary amine

The polyester polyols also found application as building blocks for polycarbonates (Fig. 2b) [47]. After the polycondensation step, the polyesters were chain extended by a two-step process using phosgene, a special amine and DMAP, which allows for an exact adjustment of the stoichiometry. The corresponding polycarbonate was obtained with a molecular weight of 48,000 g/mol. Surprisingly, the thermal properties are close to those of the lower molecular weight polyester precursors with only a slight increase of both glass transition and melting temperature. In addition, the authors state that the materials are potentially biodegradable as they are derived from renewable resources. However, no studies were conducted to confirm this statement. The same authors later tried to improve the properties by replacing some of the PDO with the cyclic building block 1,4-cyclohexanedimethanol [48]. However, the properties of the resulting polycarbonates could not be substantially improved.
Fig. 2

Polyester polyols derived from phthalic anhydride, adipic acid and a HDO or b PDO

A very interesting approach to fully bio-based polycarbonates was reported by Koning and co-workers [49]. They were synthesized by a phosgene-free reaction of limonene oxide and CO2 with high molecular weights (Mn > 10,000 g/mol). To obtain material suitable for coating applications, the polycarbonates were subsequently submitted to an alcoholysis reaction using renewable diols, such as PDO and 1,10-decanediol (scheme 2). The resulting OH-terminated polycarbonates with reduced molecular weight were preliminary examined on their potential as coating material. For this, they were mixed with a conventional isocyanate and applied on aluminum plates. The resulting coatings exhibited some interesting properties, such as good acetone resistance. In a subsequent paper, similar polycarbonates were further studied by post-polymerization modification [50]. In addition, the coating properties were examined in more detail, showing a high hardness of the polycarbonate coatings.
Scheme 2

Synthesis of poly limonene carbonate and subsequent alcoholysis with PDO

In another study the influence on the properties of PU-dispersions were examined when PDO was used to replace 1,6-hexanediol (HDO) in the polyester polyol (Fig. 2) [51]. In a first step, the polyesters were synthetized by polycondensation of the two respective diols with adipic acid and phthalic anhydride. The hydrolysis resistance of the two different polyols was examined at a buffered pH value of 4 and 80 °C. In both cases, the molecular weight of the polyesters decreased slowly, with no significant difference when PDO or HDO are used as building block. Both polyesters were then used as polyol compounds for PU-dispersions synthesized by the acetone process. The solid content of the final dispersions was adjusted to 40%. The PU-dispersions were then blended with a commercially available acrylic resin and the blend was coated on wood panels. Weathering test revealed a significant difference in the performance between the blends and the pure acrylic resin used as a reference, with the blend outperforming the acrylic resin.

In 2012 Schirp et al. [52] reported the use of PDO as diol component in PU-dispersions derived from fatty acid-derived polyester polyols. The latter were synthesized by reacting either fatty acids or fatty acid methyl esters with trimethylolpropane (TMP), isophthalic acid and PDO. The resulting dispersions exhibited a good particle size distribution and stability. In addition, the authors were able to show that the surface structure of the coated and dried dispersion strongly correlate to the amount of 2,2-bis(hydroxymethyl)propionic acid (bis-MPA).

More recently, another example of fully bio-based polyester polyols for polyurethanes coating was presented by García González and co-workers [53]. Based on a partially bio-based polyester binder that was reported by the same authors earlier [54], this new polyester was synthesized from glycerol, PDO, succinic acid, and FDCA (Fig. 3). The latter was used as a replacement for the previously used terephthalic acid. The properties of three different polyesters (0, 75, and 100% bio-derived) and the resulting polyurethane materials derived from these three polyesters by a reaction with a petrochemical derived diisocyanate were studied. It could be shown that the polyesters exhibited similar molecular weights from 1200 to 1800 g/mol, with the bio-based polyesters having a slightly lower Tg compared to the polyester derived from fossil resources. This was also true for the PU materials (14 °C against 34 °C for the petrochemical-derived PU). However, the PU derived from the 100% bio-based polyester proved to have superior properties than its fossil counterpart, such as better adhesion, higher stiffness and improved surface tension. In addition to the synthesis and material properties, the production, synthesis and recycling was evaluated by means of LCA. It was shown that the bio-based PU emits 5.5 times less greenhouse gases and exhibits a total non-renewable energy use that is 2.5 times lower compared to the fossil-based material.
Fig. 3

Polyester polyol derived from 100% bio-based building blocks

2.2 Alkyd Resins

PDO has also been used as diol component in bio-based waterborne alkyd resins. Acar and co-workers prepared acryl modified water reducible alkyd resins, where besides TMP, PDO was used as sole alcohol component [55]. The solid content of the acrylic modified alkyd resins was 60 weight-%. The others blended the resin with different ratios of an acrylic co-polymer, which resulted in an improved performance of the final coatings. The best properties were found, when 40% (in respect to the alkyd resin) of the acrylic co-polymer was used. In a consecutive study, the same authors investigated the dilution effect of this kind of acrylic modified alkyd resin on the coating properties, such as film formation and thermal behavior [56].

2.3 Coil Coating

Polyester derived from FDCA, succinic acid, isosorbide and either PDO or 1,5-pentanediol (PeDO) have been examined in coil coatings applications by Lomelí-Rodríguez [57]. Increasing the ratio of FDCA led to an increase in viscosity, molecular weight, but also in coloring. Polyesters synthesized from PDO instead of PeDO were less disperse (1.3–1.6 against 1.5–2.4 with PeDO). Increasing the amount of isosorbide led to a decrease in MW, therefore the amount of isosorbide must stay under 50 mol % of the diol component. The incorporation of FDCA as well as isosorbide had a positive effect on the Tg, as well as Tm, with isosorbide having a bigger influence. The use of PDO also improved the Tg and Tm, due to the lower chain flexibility of the shorter PDO chain. In addition, the polyester derived from IS and PDO exhibited a higher decomposition temperature compared to the similar polyester synthesized from PeDO.

2.4 Powder Coatings

PDO was also examined as diol component in carboxyl functional polyesters in the field of powder coatings [58]. In this case, the powder coatings were formulated with triglycidyl isocyanurate (TGIC) as hardener. It was shown that the coatings based on polyester with PDO exhibited a superior impact resistance and flexibility in comparison with those without PDO. However, in this example PDO is the only bio-derived monomer used.

To increase the amount of bio-based monomers in powder coatings Koning and co-workers examined the use of PDO in combination with succinic acid and isosorbide [59]. The latter was used as bio-based alternative to isophthalic and terephthalic acid to obtain polyester oligomers with high Tg necessary for powder coatings applications (scheme 3). It was shown that PDO can be used to modify the Tg. Due to the flexibility of this aliphatic monomer, the Tg decreases with increasing amount of PDO. This shows that PDO could be an alternative to petrochemical aliphatic diols such as HDO.
Scheme 3

Bio-based polyesters based on succinic acid, isosorbide and PDO

2.5 Unsaturated Polyesters

Unsaturated polyesters derived from PDO and itaconic acid were used as shape memory polymers (SMP) [60]. In this example, the synthesized SMP were almost exclusively composed of bio-based monomers, such as itaconic acid, sebacic acid and PDO. As only exception, diethylene glycol was incorporated to influence the crystallinity of the polymers (scheme 4). These polyesters were then subjected to compression molding with dicumyl peroxide as radical initiator resulting in a set of SMP with interesting properties and potential fields of application.
Scheme 4

SMP derived from polyesters with PDO

1,3-Propanediol was also used as the only diol building block for unsaturated polyester resins [61]. These resins were then used as precursor for thermally curing composites with nanoprecipitated calcium carbonate (NPCC). As other components fumaric acid, succinic acid, and lactic acid were used, resulting in a polyester with a high amount of bio-based monomers. The resins were characterized my means of IR and NMR. In addition to these resins, the authors synthesized a novel reactive diluent as partial replacement for styrene. This reactive diluent was obtained by a reaction of lactic acid with 1,2-propandiol, followed by an end-capping reaction with itaconic anhydride. The resins were subsequently cured with different amounts of reactive diluents (styrene and the bio-based component) and NPCC. It could be shown that the bio-based reactive diluent had a major influence on the properties of the composites.

As another example in the field of unsaturated polyesters, Farmer et al. [62] reported their study on the synthesis of itaconic- and fumaric acid-containing polyesters starting from the corresponding methylesters of itaconic and fumaric acid. Besides PDO, 1,4-butanediol (1,4-BDO) was used as diol component for these completely bio-based polyesters (Fig. 4).
Fig. 4

Bio-based polyesters synthesized by Farmer et al. [62]

The structure of the polyesters as well as side reactions occurring during the polycondensation reaction were thoroughly studied by means of NMR spectroscopy. For example, the degree of mesomerization of the itaconic to the corresponding mesaconic acid species was analyzed. Furthermore NMR was used to elucidate the multiplet complexity of the protons in a-position to the C–O-bond of the ester linkage. In addition, the crosslinking mechanism of polyester itaconates was examined. According to their studies, the crosslinking proceeds through an oxo-Michael-addition, the so called Ordelt reaction [63, 64, 65]. However, the abilities of these polyesters to undergo radical crosslinking or post-polymerization modification was not further examined in the course of this study.

In a recent example, PDO was also used as building block for unsaturated polyesters with itaconic acid as dicarboxylic acid [66]. Polyesters of this kind have been used as binder resins for wood coatings [51, 67]. However, the use of PDO under acid-catalyzed azeotropic polycondensation conditions led to undesired cross-linking and gelation. An effect that is not observed, when other diols, such as HDO or neopentylglycol were used. By screening at set of different Brønsted- and Lewis acids as condensation catalysts, it could be shown, that the use of Brønsted acids, such as methanesulfonic acid leads to an enhanced rate of a competing etherification reaction. This eventually leads in combination with some crosslinking through radical or polar pathways to the gelation of the polyester. This etherification is observed to a much smaller degree, when Lewis acids, such as Zn(OAc)2 or Ti(OBu)4 are used. By employing these catalysts, the gelation can be prevented and polyesters with 100% PDO can be synthesized, setting the stage for the replacement of petrochemical diols with the bio-based PDO. Polyesters of this type have been employed as binder resins in UV-curing offset inks, resulting in binder resins with a renewable content from 47 to 100%, replacing commonly used diols in the preparation of polyester polyols [68].

3 Conclusion

The aim of this mini review was to highlight the potential of PDO in the field of coating resins. Even though a lot of work has been dedicated to plastics derived from this interesting diol, such as PTT or PFT, examples in the coatings field are still somewhat scarce, especially in the scientific literature. The examples presented herein show that PDO can be used as building blocks in a broad field of application, such as polyurethane, polycarbonate, alkyd, and unsaturated polyester resins. In addition, some applications in powder and coil coatings were given. It is worth mentioning that most of the studies focus on other aspects than the mere replacement of traditional diols with PDO. However, the wide range of applications show that PDO can be a bio-based alternative to diols usually used as monomers in the field of polyester resins, such as HDO or neopentylglycol. Depending on the diol being substituted and the composition of the polyester, it can alter the Tg and flexibility of the polymers, allowing for new properties of the resulting materials. PDO can therefore be considered as an additional and valuable tool in the toolbox of polymeric chemistry, for plastics as well as coating materials.

Notes

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

References

  1. 1.
    World Economic Forum, Ellen MacArthur Foundation and McKinsey & Company (2016) The new plastics economy—Rethinking the future of plastics. https://www.ellenmacarthurfoundation.org/publications/the-new-plastics-economy-rethinking-the-future-of-plastics
  2. 2.
    Fakirov S (ed) (2015) Biodegradable polyesters. Wiley, WeinheimGoogle Scholar
  3. 3.
    Auras RA, Lim LT, Selke SEM, Tsuji H (2010) Poly (lactic acid): synthesis, structures, properties, processing, and applications. Wiley, HobokenCrossRefGoogle Scholar
  4. 4.
    Endres H-J, Siebert-Raths A (2011) Engineering biopolymers: markets, manufacturing, properties and applications. Hanser, MunichCrossRefGoogle Scholar
  5. 5.
    Hamad K, Kaseem M, Ayyoob M, Joo J, Deri F (2018) Polylactic acid blends: the future of green, light and tough. Prog Polym Sci 85:83–127CrossRefGoogle Scholar
  6. 6.
    Li Z, Yang J, Loh XJ (2016) Polyhydroxyalkanoates: opening doors for a sustainable future. NPG Asia Mater 8:e265CrossRefGoogle Scholar
  7. 7.
    Philip S, Keshavarz T, Roy I (2007) Polyhydroxyalkanoates: biodegradable polymers with a range of applications. J Chem Technol Biotechnol 82:233–247CrossRefGoogle Scholar
  8. 8.
    Możejko-Ciesielska J, Kiewisz R (2016) Bacterial polyhydroxyalkanoates: still fabulous? Microbiol Res 192:271–282CrossRefGoogle Scholar
  9. 9.
    Anjum A, Zuber M, Zia KM, Noreen A, Anjum MN, Tabasum S (2016) Microbial production of polyhydroxyalkanoates (PHAs) and its copolymers: a review of recent advancements. Int J Biol Macromol 89:161–174CrossRefGoogle Scholar
  10. 10.
    Muller J, González-Martínez C, Chiralt A (2017) Combination Of Poly(lactic) acid and starch for biodegradable food packaging. Materials 10:952CrossRefGoogle Scholar
  11. 11.
    Murariu M, Dubois P (2016) PLA composites: from production to properties. Adv Drug Deliv Rev 107:17–46CrossRefGoogle Scholar
  12. 12.
    Narayanan G, Vernekar VN, Kuyinu EL, Laurencin CT (2016) Poly (lactic acid)-based biomaterials for orthopaedic regenerative engineering. Adv Drug Deliv Rev 107:247–276CrossRefGoogle Scholar
  13. 13.
    Rabnawaz M, Wyman I, Auras R, Cheng S (2017) A roadmap towards green packaging: the current status and future outlook for polyesters in the packaging industry. Green Chem 19:4737–4753CrossRefGoogle Scholar
  14. 14.
    Jain A, Kunduru KR, Basu A, Mizrahi B, Domb AJ, Khan W (2016) Injectable formulations of poly(lactic acid) and its copolymers in clinical use. Adv Drug Deliv Rev 107:213–227CrossRefGoogle Scholar
  15. 15.
    Gandini A, Lacerda TM (2015) From monomers to polymers from renewable resources: recent advances. Prog Polym Sci 48:1–39CrossRefGoogle Scholar
  16. 16.
    Gandini A, Lacerda TM, Carvalho AJF, Trovatti E (2016) Progress of polymers from renewable resources: furans, vegetable oils, and polysaccharides. Chem Rev 116:1637–1669CrossRefGoogle Scholar
  17. 17.
    Gandini A (2008) Polymers from renewable resources: a challenge for the future of macromolecular materials. Macromolecules 41:9491–9504CrossRefGoogle Scholar
  18. 18.
    Mathers RT, Meier MAR (2011) Green polymerization methods: renewable starting materials, catalysis and waste reduction. Wiley, WeinheimCrossRefGoogle Scholar
  19. 19.
    Papageorgiou GZ, Papageorgiou DG, Terzopoulou Z, Bikiaris DN (2016) Production of bio-based 2,5-furan dicarboxylate polyesters: recent progress and critical aspects in their synthesis and thermal properties. Eur Polym J 83:202–229CrossRefGoogle Scholar
  20. 20.
    Vilela C, Sousa AF, Fonseca AC, Serra AC, Coelho JFJ, Freire CSR, Silvestre AJD (2014) The quest for sustainable polyesters–insights into the future. Polym Chem 5:3119–3141CrossRefGoogle Scholar
  21. 21.
    Zhu Y, Romain C, Williams CK (2016) Sustainable polymers from renewable resources. Nature 540:354CrossRefGoogle Scholar
  22. 22.
    Zia KM, Noreen A, Zuber M, Tabasum S, Mujahid M (2016) Recent developments and future prospects on bio-based polyesters derived from renewable resources: a review. Int J Biol Macromol 82:1028–1040CrossRefGoogle Scholar
  23. 23.
    Arntz D, Haas T, Müller A, Wiegand N (1991) Kinetische untersuchung zur hydratisierung von acrolein. Chem Ing Tech 63:733–735CrossRefGoogle Scholar
  24. 24.
    Slaugh LH, Powell JB, Forschner TC, Semple TC, Weider PR (1995) Process for preparing 1,3-propandiol, US Patent 5,463,346.Google Scholar
  25. 25.
    Nakamura CE, Whited GM (2003) Metabolic engineering for the microbial production of 1,3-propanediol. Curr Opin Biotechnol 14:454–459CrossRefGoogle Scholar
  26. 26.
    Saltzberg MA, Byrne AM, Jackson EN, Miller ES, Nelson MJ, Tyreus BD, Zhu Q (2016) DuPont: biorenewables at E.I. DU Pont DE Nemours & Co. In: Domínguez de María P (ed) Industrial biorenewables: a practical viewpoint. Wiley, Hoboken, pp 175–217Google Scholar
  27. 27.
    Whinfield JR, Dickson JT (1941) Improvements Relating to the Manufacture of Highly Polymeric Substances, US Patent 2,465,319.Google Scholar
  28. 28.
    Desborough IJ, Hall IH, Neisser JZ (1979) Structure of Poly (trimethylene terephthalate). Polymer 20:545–552CrossRefGoogle Scholar
  29. 29.
    Roupakias CP, Bikiaris DN, Karayannidis GP (2005) Synthesis, thermal characterization, and tensile properties of alipharomatic polyesters derived from 1,3-propanediol and terephthalic, isophthalic, and 2,6-naphthalenedicarboxylic acid. J Polym Sci Part A Polym Chem 43:3998–4011CrossRefGoogle Scholar
  30. 30.
    Fehrenbacher U, Grosshardt O, Kowollik K, Tübke B, Dingenouts N, Wilhelm M (2009) Synthese und charakterisierung von polyestern und polyamiden auf der basis von furan-2,5-dicarbonsäure. Chem Ing Tech 81:1829–1835CrossRefGoogle Scholar
  31. 31.
    Gomes M, Gandini A, Silvestre AJD, Reis B (2011) Synthesis and characterization of poly(2,5-furan dicarboxylate)s based on a variety of diols. J Polym Sci Part A Polym Chem 49:3759–3768CrossRefGoogle Scholar
  32. 32.
    Papageorgiou GZ, Papageorgiou DG, Tsanaktsis V, Bikiaris DN (2015) Synthesis of the bio-based polyester poly(propylene 2,5-furan dicarboxylate). Comparison of thermal behavior and solid state structure with its terephthalate and naphthalate homologues. Polymer 62:28–38CrossRefGoogle Scholar
  33. 33.
    Ward IM, Wilding MA, Brody H (1976) The mechanical properties and structure of poly(m-methylene terephthalate) fibers. J Polym Sci Polym Phys Edit 14:263–274CrossRefGoogle Scholar
  34. 34.
    Vannini M, Marchese P, Celli A, Lorenzetti C (2015) Fully biobased poly(propylene 2,5-furandicarboxylate) for packaging applications: excellent barrier properties as a function of crystallinity. Green Chem 17:4162–4166CrossRefGoogle Scholar
  35. 35.
    Hbaieb S, Kammoun W, Delaite C, Abid M, Abid S, El Gharbi R (2015) New copolyesters containing aliphatic and bio-based furanic units by bulk copolycondensation. J Macromol Sci Part A 52:365–373CrossRefGoogle Scholar
  36. 36.
    Bikiaris DN, Papageorgiou GZ, Achilias DS (2006) Synthesis and comparative biodegradability studies of three poly(alkylene succinate)s. Polym Degrad Stab 91:31–43CrossRefGoogle Scholar
  37. 37.
    Bikiaris DN, Papageorgiou GZ, Giliopoulos DJ, Stergiou CA (2008) Correlation between chemical and solid-state structures and enzymatic hydrolysis in novel biodegradable polyesters. The case of Poly(propylene alkanedicarboxylate)s. Macromol Biosci 8:728–740CrossRefGoogle Scholar
  38. 38.
    Debuissy T, Pollet E, Averous L (2017) Synthesis and characterization of fully biobased Poly(propylene succinate-ran-propylene adipate). Analysis of the Architecture-Dependent Physicochemical Behavior. J Polym Sci Part A Polym Chem 55:2738–2748CrossRefGoogle Scholar
  39. 39.
    Debuissy T, Sangwan P, Pollet E, Averous L (2017) Study on the structure-properties relationship of biodegradable and biobased aliphatic copolyesters based on 1,3-propanediol, 1,4-butanediol, succinic and adipic acids. Polymer 122:105–116CrossRefGoogle Scholar
  40. 40.
    Umare SS, Chandure AS, Pandey RA (2007) Synthesis, characterization and biodegradable studies of 1,3-propanediol based polyesters. Polym Degrad Stab 92:464–479CrossRefGoogle Scholar
  41. 41.
    Liu H, Ou X, Zhou S, Liu D (2010) Microbial 1,3-propanediol, its copolymerization with terephthalate, and applications. In: Chen G-Q (ed) Plastics from bacteria: natural functions and applications. Springer, Berlin, pp 405–425CrossRefGoogle Scholar
  42. 42.
    Liu H, Xu Y, Zheng Z, Liu D (2010) 1,3-Propanediol and its copolymers: research, development and industrialization. Biotechnol J 5:1137–1148CrossRefGoogle Scholar
  43. 43.
    Sousa AF, Vilela C, Fonseca AC, Matos M, Freire CSR, Gruter G-JM, Coelho JFJ, Silvestre AJD (2015) Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency. Polym Chem 6:5961–5983CrossRefGoogle Scholar
  44. 44.
    Achilias DS, Bikiaris DN (2015) Synthesis, properties, and mathematical modeling of biodegradable aliphatic polyesters based on 1,3-propanediol and dicarboxylic acids. Biodegradable polyesters. Wiley, Weinheim, pp 73–108Google Scholar
  45. 45.
    Papageorgiou GZ, Bikiaris DN (2008) Biodegradable aliphatic polyesters derived from 1,3-propanediol: current status and promises. In: Yamashita H, Nakano Y (eds) Polyester: properties, preparation and applications. Nova Science Publishers, New York, pp 147–173Google Scholar
  46. 46.
    Liu Y, Söderqvist Lindblad M, Ranucci E, Albertsson A-C (2001) New segmented poly(ester-urethane)s from renewable resources. J Polym Sci Part A Polym Chem 39:630–639CrossRefGoogle Scholar
  47. 47.
    Ranucci E, Liu Y, Söderqvist Lindblad M, Albertsson A-C (2000) New biodegradable polymers from renewable sources: High molecular weight poly(ester carbonate)s from succinic acid and 1,3-propanediol. Macromol Rapid Commun 21:680–684CrossRefGoogle Scholar
  48. 48.
    Liu Y, Ranucci E, Söderqvist Lindblad M, Albertsson A-C (2001) New biodegradable polymers from renewable sources: Polyester-carbonates based on 1,3-propylene-co-1,4-cyclohexanedimethylene succinate. J Polym Sci Part A Polym Chem 39:2508–2519CrossRefGoogle Scholar
  49. 49.
    Li C, Sablong RJ, Koning CE (2015) Synthesis and characterization of fully-biobased α, ω-dihydroxyl poly(limonene carbonate)s and their initial evaluation in coating applications. Eur Polymer J 67:449–458CrossRefGoogle Scholar
  50. 50.
    Li C, van Berkel S, Sablong RJ, Koning CE (2016) Post-functionalization of fully biobased poly(limonene carbonate)s: synthesis, characterization and coating evaluation. Eur Polym J 85:466–477CrossRefGoogle Scholar
  51. 51.
    Daniliuc A, Deppe B, Deppe O, Friebel S, Kruse D, Philipp C (2012) New trends in wood coatings and fire retardants. Eur Coat J 7/8:20–25Google Scholar
  52. 52.
    Philipp C, Eschig S (2012) Waterborne polyurethane wood coatings based on rapeseed fatty acid methyl esters. Prog Org Coat 74:705–711CrossRefGoogle Scholar
  53. 53.
    García González MN, Börjesson P, Levi M, Turri S (2018) Development and life cycle assessment of polyester binders containing 2,5-Furandicarboxylic acid and their polyurethane coatings. J Polym Environ 26:3626–3637CrossRefGoogle Scholar
  54. 54.
    Gao C, Han S, Zhang D, Wang B, Wang C, Wu Y, Liu Y (2018) A facile preparation of UV-cured films from waterborne unsaturated polyester via click reaction. Prog Org Coat 124:232–239CrossRefGoogle Scholar
  55. 55.
    Akgün N, Büyükyonga ÖN, Acar I, Güçlü G (2016) Synthesis of novel acrylic modified water reducible alkyd resin: investigation of acrylic copolymer ratio effect on film properties and thermal behaviors. Polym Eng Sci 56:947–954CrossRefGoogle Scholar
  56. 56.
    Büyükyonga ÖN, Akgün N, Acar I, Güçlü G (2017) Synthesis of four-component acrylic-modified water-reducible alkyd resin: investigation of dilution ratio effect on film properties and thermal behaviors. J Coat Technol Res 14:117–128CrossRefGoogle Scholar
  57. 57.
    Lomelí-Rodríguez M, Corpas-Martínez J, Willis S, Mulholland R, Lopez-Sanchez J (2018) Synthesis and characterization of renewable polyester coil coatings from biomass-derived Isosorbide, FDCA, 1,5-pentanediol, succinic acid, and 1,3-propanediol. Polymers 10:600CrossRefGoogle Scholar
  58. 58.
    Thames SF, Zhou L, Smith OW, Boon WH, Forschner TC (2000) Polyester powder coatings based on 1,3-propanediol. Abstr Pap Am Chem Soc 219:U481–U481Google Scholar
  59. 59.
    Noordover BAJ, van Staalduinen VG, Duchateau R, Koning CE, van Benthem R, Mak M, Heise A, Frissen AE, van Haveren J (2006) Co- and terpolyesters based on isosorbide and succinic acid for coating applications: synthesis and characterization. Biomacromol 7:3406–3416CrossRefGoogle Scholar
  60. 60.
    Guo B, Chen Y, Lei Y, Zhang L, Zhou WY, Rabie ABM, Zhao J (2011) Biobased poly(propylene sebacate) as shape memory polymer with tunable switching temperature for potential biomedical applications. Biomacromol 12:1312–1321CrossRefGoogle Scholar
  61. 61.
    Fonseca AC, Costa CSMF, Marques TMP, Coelho JFJ, Serra AC (2017) The impact of a designed lactic acid-based crosslinker in the thermochemical properties of unsaturated polyester resins/nanoprecipitated calcium carbonate composites. J Mater Sci 52:1272–1284CrossRefGoogle Scholar
  62. 62.
    Farmer T, Castle R, Clark J, Macquarrie D (2015) Synthesis of unsaturated polyester resins from various bio-derived platform molecules. Int J Mol Sci 16:14912CrossRefGoogle Scholar
  63. 63.
    Ordelt VZ (1963) Über die Reaktion von Glykolen mit der olefinischen Doppelbindung bei der Darstellung von ungesättigten Polyestern durch Schmelzkondensation. Die Makromolekulare Chemie 63:153–161CrossRefGoogle Scholar
  64. 64.
    Ordelt Z, Krátký B (1969) Aufgabe der Reaktionssteuerung bei der Synthese von ungesättigten Polyestern aus Maleinsäureanhydrid. Farbe und Lack 6:523–531Google Scholar
  65. 65.
    Lehtonen J, Salmi T, Immonen K, Paatero E, Nyholm P (1996) Kinetic model for the homogeneously catalyzed polyesterification of dicarboxylic acids with diols. Ind Eng Chem Res 35:3951–3963CrossRefGoogle Scholar
  66. 66.
    Schoon I, Kluge M, Eschig S, Robert T (2017) Catalyst influence on undesired side reactions in the polycondensation of fully bio-based polyester itaconates. Polymers 9:693CrossRefGoogle Scholar
  67. 67.
    Robert T, Friebel S (2016) Itaconic acid—a versatile building block for renewable polyesters with enhanced functionality. Green Chem 18:2922–2934CrossRefGoogle Scholar
  68. 68.
    Robert T, Eschig S, Biemans T, Scheifler F (2018) Bio-based polyester itaconates as binder resins for UV-curing offset printing inks. J Coat Technol Res.  https://doi.org/10.1007/s11998-018-0146-4 Google Scholar

Copyright information

© The Tunisian Chemical Society and Springer Nature Switzerland AG 2018

Authors and Affiliations

  1. 1.Fraunhofer Institute for Wood Research — Wilhelm-Klauditz-Institut WKIBrunswickGermany

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