Synthesis and ring-opening reactions of tetraphenyl-substituted bisoxazoline monomers for preparing new thermosets and composites

Culbertson, B. M.; Tong, Yuhua; Schricker, Scott R.

doi:10.1002/(sici)1099-1581(200001)11:1<9::aid-pat923>3.0.co;2-i

Cited by 7 publications

(4 citation statements)

References 8 publications

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“…As far as we know, the substance has not yet been used for the cationic ring-opening polymerization. After purification, the monomer was obtained as a colorless crystalline solid with a melting point comparable to the literature (110°C , lit: 107-109 °C) [46] (Figure S3). The substance was further analyzed by 1 H-and 13 C NMR spectroscopy (supporting info Figure S2).…”

Section: Monomer Synthesismentioning

confidence: 55%

ABA Type Amphiphiles with Poly(2-Benzhydryl-2-Oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

Hahn¹,

Keßler²,

Polzin³

et al. 2021

Preprint

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<div>Thermoresponsive polymers are frequently discussed for various applications. Here, we introduce a novel amphiphilic triblock copolymer, which undergoes inverse thermogelation, i.e. is forms a physical gel upon cooling. The polymers comprises poly(2-benzhydryl-2-oxazine) as the hydrophobic building block, a polymer which has not been reported to date. The physical gels are surprisingly strong with a storage modulus of 22 kPa at 25 wt.% in water. In addition, relatively high yield and flow points were determined by rheology.</div>

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Section: Monomer Synthesismentioning

confidence: 55%

ABA Type Amphiphiles with Poly(2-Benzhydryl-2-Oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

Hahn¹,

Keßler²,

Polzin³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…As far as we know, the substance has not yet been used for the cationic ring-opening polymerization. After purification, the monomer was obtained as a colorless crystalline solid with a melting point comparable to the literature (110°C, lit: 107-109°C) [46] (Figure S3, Supporting Information). The substance was further analyzed by 1 H-and 13 C NMR spectroscopy (Figure S2, Supporting Information).…”

Section: Monomer Synthesismentioning

confidence: 66%

“…[45] The monomer BhOx (Figure S1, Supporting Information) was already synthesized by Culbertson in 2000. [46] It was further converted to a bisoxazoline and then the first ring-opening reactions were carried out. As far as we know, the substance has not yet been used for the cationic ring-opening polymerization.…”

Section: Monomer Synthesismentioning

confidence: 99%

ABA Type Amphiphiles with Poly(2‐benzhydryl‐2‐oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

Hahn¹,

Keßler

Polzin³

et al. 2021

Macro Chemistry & Physics

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Thermoresponsive polymers are frequently involved in the development of materials for various applications. Here, polymers containing poly(2benzhydryl-2-oxazine) (pBhOzi) repeating units are described for the first time. The homopolymer pBhOzi and an ABA type amphiphile comprising two flanking hydrophilic A blocks of poly(2-methyl-2-oxazoline) (pMeOx) and the hydrophobic aromatic pBhOzi central B block (pMeOx-b-pBhOzi-b-pMeOx) are synthesized and the latter is shown to exhibit inverse thermogelling properties at concentrations of 20 wt.% in water. This behavior stands in contrast to a homologue ABA amphiphile consisting of a central poly(2-benzhydryl-2-oxazoline) block (pMeOx-b-pBhOx-b-pMeOx). No inverse thermogelling is observed with this polymer even at 25 wt.%. For 25 wt.% pMeOx-b-pBhOzi-b-pMeOx, a surprisingly high storage modulus of ≈22 kPa and high values for the yield and flow points of 480 Pa and 1.3 kPa are obtained. Exceeding the yield point, pronounced shear thinning is observed. Interestingly, only little difference between self-assemblies of pMeOx-b-pBhOzi-b-pMeOx and pMeOx-b-pBhOx-b-pMeOx is observed by dynamic light scattering while transmission electron microscopy images suggest that the micelles of pMeOx-b-pBhOzi-b-pMeOx interact through their hydrophilic coronas, which is probably decisive for the gel formation. Overall, this study introduces new building blocks for poly(2-oxazoline) and poly(2-oxazine)-based self-assemblies, but additional studies will be needed to unravel the exact mechanism.

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“…[45] The monomer 2-benzhydryl-2-oxazoline (Figure S1) was already synthesized by Culbertson in 2000. [46] It was further converted to a bisoxazoline and then the first ring-opening reactions were carried out. As far as we know, the substance has not yet been used for the cationic ring-opening polymerization.…”

Section: Monomer Synthesismentioning

confidence: 99%

ABA Type Amphiphiles with Poly(2-Benzhydryl-2-Oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

Hahn¹,

Keßler²,

Polzin³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

Synthesis and ring-opening reactions of tetraphenyl-substituted bisoxazoline monomers for preparing new thermosets and composites

Cited by 7 publications

References 8 publications

ABA Type Amphiphiles with Poly(2-Benzhydryl-2-Oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

ABA Type Amphiphiles with Poly(2-Benzhydryl-2-Oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

ABA Type Amphiphiles with Poly(2‐benzhydryl‐2‐oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

ABA Type Amphiphiles with Poly(2-Benzhydryl-2-Oxazine) Moieties: Synthesis, Characterization and Inverse Thermogelation

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