Nonmigratory internal plasticization of poly(vinyl chloride) via pendant triazoles bearing alkyl or polyether esters

Higa, Chad M.; Tek, Andy T.; Wojtecki, Rudy J.; Braslau, Rebecca

doi:10.1002/pola.29205

Cited by 25 publications

(30 citation statements)

References 63 publications

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“…To examine the effect of doubling the density of ester plasticizing moieties using this branched linker, a comparison with TEGMe dieaters plasticizers 7 and 7′ from previous work in the Braslau lab is useful (Scheme ). For 4 mol % PVC samples, the T g value of diester 7 = 61 °C, whereas for the tetraester 6e , the T g = 40 °C.…”

Section: Resultsmentioning

confidence: 99%

“…In order to evaluate the efficacy of plasticization, T g values of these branched internally plasticized PVC samples were compared to that of externally plasticized DEHP‐PVC as a function of plasticizer content by weight percentage [Fig. (a)].…”

Section: Resultsmentioning

confidence: 99%

“…PVC (25.00 g, 400 mmol) was dissolved in THF (250 mL) . The solution was precipitated in MeOH (1 L).…”

Section: Methodsmentioning

confidence: 99%

“…To a 50 mL round bottom flask was added PVC‐4.4%‐N 3 5 (805.2 mg, 12.88 mmol), alkyne 2a (384.3 mg, 0.6440 mmol), and 3‐pentanone (8 mL) . The reaction mixture was heated to 90 °C for 48 h. The resulting polymer was purified via precipitation in 100 mL of MeOH three times.…”

Section: Methodsmentioning

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%

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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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…PVC (25.00 g, 400 mmol) was dissolved in THF (250 mL) . The solution was precipitated in MeOH (1 L).…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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 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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Facile Preparation and Properties of Crosslinked Copolyether Elastomers with 1,2,3‐Triazole and Urethane Subunit via Click Polymerization

Zhang¹,

Liu²,

Hu³

et al. 2019

ChemistryOpen

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An azide terminated ethylene oxide‐tetrahydrofuran copolymer with urethane segments (ATUPET) as a novel binder pre‐polymer, has been prepared through ethylene oxide‐tetrahydrofuran random copolymer (PET) end‐capping modification via one‐pot method. The structure characterization of the modifier has been analyzed by FTIR, 1 H NMR, 13 C NMR and GPC. In comparison with PET, ATUPET has a slightly higher viscosity because it has additional hydrogen bonding interaction generated by the urethane in ATUPET. Triazole cross‐linked elastomers based on ATUPET with various functional molar ratios were prepared using tripropargylamine as a curing agent and cross‐linker. Mechanical properties indicate that the modulus E and tensile strength σ b exhibit a parabolic dependence with the increase in R. At around the stoichiometric ratio, the modulus E and tensile strength σ b reach a maximum and the elongation at break exhibit an acceptable value at the same time. Swelling tests demonstrate that the apparent cross‐linking densities (N 0 ) have a maximum value at the stoichiometric ratio. Thermal analysis shows that the ATUPET prepolymer and its polytriazoles elastomers exhibit a satisfactory stability. The results demonstrated that ATUPET might be a promising polymeric binder for future propellant formulations especially in the field of isocyanate‐free curing technology.

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Nonmigratory internal plasticization of poly(vinyl chloride) via pendant triazoles bearing alkyl or polyether esters

Cited by 25 publications

References 63 publications

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 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

Facile Preparation and Properties of Crosslinked Copolyether Elastomers with 1,2,3‐Triazole and Urethane Subunit via Click Polymerization

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