Ester plasticizers for polyvinyl chloride

Lakeev, S. N.; Maydanova, I. O.; Mullakhmetov, R. F.; Давыдова, О. В.

doi:10.1134/s1070427216010018

Cited by 16 publications

(7 citation statements)

References 27 publications

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“…Primary external plasticizers are highly compatible with the polymer and can be added in large quantities, while secondary plasticizers have high volatility or only limited compatibility with the polymer and are used in combination with primary plasticizers. 11,30 Plasticizers must solvate the polymer and cannot be prone to self-association, which makes esters appropriate compounds. Ideally, plasticizers should be stable, non-toxic, non-volatile, odourless, colourless liquids.…”

Section: Plasticization Of Poly(vinyl Chloride)mentioning

confidence: 99%

“…35 Diesters of terephthalic acid have replaced DEHP in many applications, including sensitive products such as toys, medical and food products. 30 Hydrogenation of ortho-phthalates produces 1,2-cyclohexane dicarboxylates which are also used as plasticizers. Mono-and di-benzoates of branched C 8 -C 10 alcohols are often used as secondary plasticizers due to their high compatibility and high solvating power.…”

Section: Types Of Plasticizersmentioning

confidence: 99%

“…Other plasticizers derived from raw materials, especially citrates, succinates, triglycerides, sugar derivatives and fatty acid esters have been synthesized and used as alternative plasticizers. 30,41 New biobased plasticizers were tested in finished PVC formulation. Despite the accelerated degradation tests of emerging plasticizers, there are still uncertainties about the natural lifelong stability and performance of PVC products created with emerging plasticizers.…”

Section: Types Of Plasticizersmentioning

confidence: 99%

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Plastics in Heritage Collections: Poly(vinyl chloride) Degradation and Characterization

Rijavec

2020

ACSi

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Museums and galleries house increasingly large collections of objects and contemporary art made of plastic materials, many of which undergo rapid material change. The main degradation processes of poly(vinyl chloride) (PVC) are elimination of HCl and plasticizer migration or leaching. This results in visible discolouration, stickiness and cracking. Degradation is known to be a multi-stage process that includes HCl elimination, formation of conjugated polyenes and cross-linking. Elimination of HCl begins due to structural irregularities (allylic and tertiary chlorides) and results in the formation of polyenes. When at least 7 conjugated double bonds are present, discolouration of PVC becomes visible. Non-invasive techniques, such as IR and Raman spectroscopy are used for polymer identification and plasticizer quantification. Plasticizer degradation and particularly the late stages of PVC degradation can be investigated using SEC, GC-MS, TGA and DSC. Studies in heritage collections have revealed that, apart from HCl, PVC objects emit 2-ethylhexanol and other volatile degradation products, however, there is currently no indication that HCl is emitted at usual indoor conditions. There seems to be a general lack of systematic research into PVC degradation at the conditions of storage and display, which could result in the development of dose-response functions and in the development of preventive conservation guidelines for the management of PVC collections.

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Section: Plasticization Of Poly(vinyl Chloride)mentioning

confidence: 99%

Section: Types Of Plasticizersmentioning

confidence: 99%

Section: Types Of Plasticizersmentioning

confidence: 99%

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Plastics in Heritage Collections: Poly(vinyl chloride) Degradation and Characterization

Rijavec

2020

ACSi

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“…The raw material for its production is easily available, biodegradable, and has a relatively low price [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. Another important group of bioplasticizers is esters [ 29 ], including citric acid esters [ 20 , 24 , 30 , 31 ], succinic acid esters [ 9 , 12 , 32 , 33 , 34 , 35 , 36 ], lactic acid esters [ 37 , 38 , 39 ], fatty acid esters [ 40 , 41 , 42 ], glycerol esters [ 43 ] or isosorbide esters [ 44 , 45 , 46 ].…”

Section: Introductionmentioning

confidence: 99%

Effective, Environmentally Friendly PVC Plasticizers Based on Succinic Acid

et al. 2022

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The plasticizers used in this study were synthesized from renewable raw materials using succinic acid, oleic acid, and propylene glycol. Four environmentally friendly plasticizer samples were obtained; their chemical structures and compositions were confirmed by gas chromatography (GC) and infrared spectroscopy (FT–IR) analyses, and their physicochemical properties and thermal stability (TGA analysis) were investigated. The obtained ester mixtures were used as poly(vinyl chloride) (PVC) plasticizers and their plasticization efficiency was determined in comparison to traditional, commercially available phthalate plasticizers, such as DEHP (di(2-ethylhexyl phthalate) and DINP (diisononyl phthalate). Mechanical properties and migration resistance were determined for soft PVC with the use of three concentrations of plasticizers (40 PHR, 50 PHR, and 60 PHR). It was observed that the obtained plasticizers exhibited the same plasticization efficiency and were characterized with good mechanical and physical properties in comparison to commercial plasticizers. The tensile strength was approx. 19 MPa, while the elongation at break was approx. 250% for all tested plasticizers at a concentration of 50 PHR. Furthermore, plasticizer migration studies showed that the synthesized plasticizers had excellent resistance to plasticizer leaching. The best migration test result obtained was 70% lower than that for DEHP or DINP. The ester mixture that was found to be the most favorable plasticizer was characterized by good thermal and thermo-oxidative stability (5% weight loss temperature: 227.8 °C in air and 261.1 °C in nitrogen). The results of the research clearly indicate that the synthesized esters can provide a green alternative to toxic phthalate plasticizers.

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“…Due to these big issues, the use of phthalates has been regulated and restricted especially in the manufacture of children’s toys and medical apparatuses in the USA, Canada, and Europe, strongly incentivizing the development of safer alternatives. Among the several requirements that the new generation of additives should fulfill, their renewable origin and biodegradability certainly represent one of the most important aspects. , As a result, several “greener” nonphthalate plasticizers have been proposed such as succinates, adipates, azelates, and sebacates, esters of aromatic dicarboxylic acids (mono- and dibenzoates), cyclohexanecarboxylates, norbornene derivatives, citrates, and plasticizers derived from glycerol and vegetable oils. ,− Even though some of the nonphthalate plasticizers are already commercially available, the identification and synthesis of new compounds are still important challenges since high performances and economical additives comparable with traditional phthalates have not been found yet.…”

Section: Introductionmentioning

confidence: 99%

Biobased Ketal–Diester Additives Derived from Levulinic Acid: Synthesis and Effect on the Thermal Stability and Thermo-Mechanical Properties of Poly(vinyl chloride)

Sinisi

Esposti

Toselli

et al. 2019

ACS Sustainable Chem. Eng.

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A new class of biobased plasticizers is herein proposed as a replacement of the currently used additives. The molecules were synthesized by a selective protecting-group-free route, which was developed in order to produce valuable asymmetrical ketal–diester derivatives from the renewable levulinic acid, overcoming the typical drawbacks of these types of reactions. Five molecules with different side chains were successfully obtained and fully characterized by means of NMR and FT-IR spectroscopies. These ketal–diester additives were then tested in poly(vinyl chloride) (PVC) as the model polymer. Their compatibility and plasticizing effect were evaluated by scanning electron microscopy (SEM), differential scanning calorimetry (DSC), dynamic-mechanical thermal analysis (DMTA), and thermogravimetric analysis (TGA). The emerged trend showed a clear correlation between the structural features of the ketal–ester and the thermal and mechanical properties of the material. In particular, the best results in terms of glass transition temperature reduction were achieved when the isobutyl- and benzyl-terminated additives were used. Leaching tests in both hydrophilic and hydrophobic environments were also performed. No significant aqueous leaching was found; despite the aggressive treatment in hexane, the extraction for all additives was remarkably low. Importantly, when compared to commercial plasticizers such as di-2-ethylhexyl phthalate (DEHP), 1,2-cyclohexane dicarboxylic acid diisononyl ester (Hexamoll DINCH), acetyl tributyl citrate (ATBC), and diethylhexyl adipate (DEHA), the proposed ketal–diester additives performed comparably and, in some cases, even better. In particular, it was observed that the plasticizing effect already starts at lower concentrations, permitting one to use significantly less additive to obtain a similar effect to the one achieved with the nowadays available plasticizers.

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Ester plasticizers for polyvinyl chloride

Cited by 16 publications

References 27 publications

Plastics in Heritage Collections: Poly(vinyl chloride) Degradation and Characterization

Plastics in Heritage Collections: Poly(vinyl chloride) Degradation and Characterization

Effective, Environmentally Friendly PVC Plasticizers Based on Succinic Acid

Biobased Ketal–Diester Additives Derived from Levulinic Acid: Synthesis and Effect on the Thermal Stability and Thermo-Mechanical Properties of Poly(vinyl chloride)

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