Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions

Earla, Aruna; Li, Longbo; Costanzo, Philip J.; Braslau, Rebecca

doi:10.1016/j.polymer.2016.12.014

Cited by 39 publications

(49 citation statements)

References 36 publications

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“…weaker gradually, [19][20][21][22][23]40 indicating the reaction between PVC and aminated tung oil methyl ester was completed.…”

Section: -40mentioning

confidence: 95%

“…In addition, the peaks at around 686 cm attributed to the C-Cl, [19][20][21][22][23] which appeared weak gradually with more aminated tung oil methyl ester connected to the chemical structure of selfplasticizing PVC mistrals, indicating the self-plasticizing PVC materials were gotten.…”

Section: -40mentioning

confidence: 99%

“…Though the modied PVC materials exhibited zero migration, exibility of the materials was reduced compared with PVC/phthalate systems. Earla et al 19,20 reported the covalent attachment of phthalate derivatives onto the PVC chains via click chemistry. The obtained internally plasticized PVC materials gave lower T g than PVC/ diethylhexyl phthalate (DEHP) system, which indicated that the plasticizing strategy was successful.…”

Section: -8mentioning

confidence: 99%

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Internally plasticized PVC materials via covalent attachment of aminated tung oil methyl ester

Jia

Yang

et al. 2017

RSC Adv.

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We developed an internal plasticizer of aminated tung oil methyl ester for the production of non-migration, phthalate-free flexible and internally plasticized poly(vinyl chloride) (PVC) materials. The chemical structure of the synthesized aminated tung oil methyl ester and the internally plasticized PVC materials were characterized. The obtained internally plasticized PVC materials presented a lower glass transition temperature (T g ) and were more flexible than pure PVC. The thermal stability of internally plasticized PVC materials was less thermally stable compared to those of pure PVC due to the active secondary amine groups of aminated tung oil methyl ester. However, the modified PVC materials presented no migration for self-plasticizing PVC films but 15.7% weight loss for 50 wt% of the PVC/Dioctyl phthalate (DOP) system. It is expected that the PVC materials can be widely used in areas with high migration resistance requirements.

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“…weaker gradually, [19][20][21][22][23]40 indicating the reaction between PVC and aminated tung oil methyl ester was completed.…”

Section: -40mentioning

confidence: 95%

Section: -40mentioning

confidence: 99%

Section: -8mentioning

confidence: 99%

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Internally plasticized PVC materials via covalent attachment of aminated tung oil methyl ester

Jia

Yang

et al. 2017

RSC Adv.

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“…The disadvantage of using amine nucleophiles to displace chloride on PVC is that amines are also excellent bases, leading to inevitable competitive elimination, resulting in unsaturation in the polymer chain and consequent low thermal stability . Another method to attach plasticizers to PVC is copper‐catalyzed azide‐alkyne cycloaddtion . However, the use of a copper catalyst leaves a toxic copper residue .…”

Section: Introductionmentioning

confidence: 99%

“…However, the use of a copper catalyst leaves a toxic copper residue . Previous work in the Braslau laboratory on preparing plasticizers covalently linked to PVC has utilized efficient metal‐free Huisgen thermal azide‐alkyne dipolar cycloadditions . Post‐polymerization functionalization involving azide displacement of chlorine atoms on PVC via a facile S N 2 reaction occurs with no detectable competitive elimination.…”

Section: Introductionmentioning

confidence: 99%

Internal plasticization of poly(vinyl) chloride using glutamic acid as a branched linker to incorporate four plasticizers per anchor point

Tek

Wojtecki

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Internal plasticization of polyvinyl chloride (PVC) using thermal azide‐alkyne Huisgen dipolar cycloaddition between azidized PVC and electron‐poor acetylenediamides incorporating a branched glutamic acid linker resulted in incorporation of four plasticizing moieties per attachment point on the polymer chain. A systematic study incorporating either alkyl or polyethylene glycol esters provided materials with varying degrees of plasticization, with depressed Tg values ranging from −1 °C to 62 °C. Three interesting trends were observed. First, Tg values of PVC bearing various internal plasticizers were shown to decrease with increasing chain length of the plasticizing ester. Second, branched internal plasticizers bearing triethylene glycol chains had lower Tg values compared to those with similar length long‐chain alkyl groups. Finally, thermogravimetric analysis of these internally plasticized PVC samples revealed that these branched internal plasticizers bearing alkyl chains are more thermally stable than similarity branched plasticizers bearing triethylene glycol units. These internal tetra‐plasticizers were synthesized and attached to PVC‐azide in three simple synthetic steps. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1821–1835

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Internal plasticization of poly(vinyl chloride) by grafting acrylate copolymers via copper‐mediated atom transfer radical polymerization

Schneider²,

Hoeglund³

et al. 2021

J of Applied Polymer Sci

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Internal plasticization of poly(vinyl chloride) (PVC) was achieved in one‐step using copper‐mediated atom transfer radical polymerization to graft different ratios of random n‐butyl acrylate and 2–2‐(2‐ethoxyethoxy)ethyl acrylate copolymers from defect sites on the PVC chain. Five graft polymers were made with different ratios of poly(butyl acrylate) (PBA) and poly(2–2‐(2‐ethoxyethoxy)ethyl acrylate) (P2EEA); the glass transition temperatures (Tg) of functionalized PVC polymers range from − 25 to − 50°C. Single Tg values were observed for all polymers, indicating good compatibility between PVC and grafted chains, with no evidence of microphase separation. Plasticization efficiency is higher for polyether P2EEA moieties compared with PBA components. The resultant PVC graft copolymers are thermally more stable compared to unmodified PVC. Increasing the reaction scale from 2 to 14 g produces consistent and reproducible results, suggesting this method could be applicable on an industrial scale.

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Phthalate plasticizers covalently linked to PVC via copper-free or copper catalyzed azide-alkyne cycloadditions

Cited by 39 publications

References 36 publications

Internally plasticized PVC materials via covalent attachment of aminated tung oil methyl ester

Internally plasticized PVC materials via covalent attachment of aminated tung oil methyl ester

Internal plasticization of poly(vinyl) chloride using glutamic acid as a branched linker to incorporate four plasticizers per anchor point

Internal plasticization of poly(vinyl chloride) by grafting acrylate copolymers via copper‐mediated atom transfer radical polymerization

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