Catalytic double ring-opening polyaddition of spiro orthoester with acid chloride for shrinkage-controlled molding

Nishida, Haruo; Morikawa, Hiroshi; Nakahara, Takeshi; Ogata, Takayuki; Kusumoto, Koshi; Endō, Takeshi

doi:10.1016/j.polymer.2005.02.017

Cited by 17 publications

(9 citation statements)

References 16 publications

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“…The double ring-opening polyaddition of mono- and multifunctional SOEs and acid chlorides was investigated by Nishida and coworkers [ 64 ]. The presence of various tetraphenyl phosphonium halides as catalysts enabled performance of the ring-opening reaction at room temperature with conversions of up to 100%.…”

Section: Expanding Oxacyclesmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

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Section: Expanding Oxacyclesmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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“…22 It was demonstrated that the introduction of ring-opening polymerization monomers such as the monomers with spiro ring or epoxy structure led to volume expansion that could reduce the volume shrinkage. [23][24][25][26] Introducing flexible fragment into the molecule chain and improving the flexibility of molecules should also be effective methods for reducing the volume shrinkage. Jiang 27 found that the volume shrinkage decreased with the increase of carbon chain length between double bonds of monomer, because the longer chain could lead to the lower double bond density and improve the flexibility of molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of polyurethane acrylate modified by different contents of stearyl alcohol

Qin

Nie

2014

J Coat Technol Res

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Polyurethane acrylates (PUAs) modified by different amounts of stearyl alcohol were synthesized from stearyl alcohol (SA), isophorone diisocyanate, 2-hydroxyethyl acrylate, and polycaprolactone triol. The molecular structure was characterized by Fourier transform infrared spectroscopy. Real time infrared spectroscopy was used to investigate the kinetics of photopolymerization of synthesized PUAs. The volume shrinkage was measured by laser displacement sensor. The adhesion on glass, polycarbonate (PC), and polyvinyl chloride (PVC) was tested by the laser micrometer and universal testing machine. The glass transition temperature (T g ) and storage modulus (E¢) were measured by dynamic mechanical analyzer (DMA). The pendulum hardness, pencil hardness and flexibility were also measured. The results showed that the greater the amount of SA in synthesized PUAs, the lower the volume shrinkage and the better the adhesion to glass, PC, and PVC substrates.

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“…Another problem of the epoxy resins is their shrinkage during curing, which can lead to internal compressive stress in the material, poor adhesion of coatings to the substrate, and the appearance of microvoids and microcracks, which reduce the durability of materials 10. One of the best solutions to solve the shrinkage is the use of monomers that show no volume shrinkage in their polymerization, such as spiroorthoesters (SOEs),11, 12 spiroorthocarbonates (SOCs),13, 14 and bicyclicorthoesters (BOEs) 15…”

Section: Introductionmentioning

confidence: 99%

Novel silicon‐containing spiroorthoester to confer combined flame retardancy and low shrinkage properties to epoxy resins

Canadell

Mantecón

Cádiz

2007

J. Polym. Sci. A Polym. Chem.

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A new silicon‐containing spiroorthoester, 1,4,6‐trioxaspiro [4,4]‐2‐nonylmethyl 3‐trimethylsilyl propionate (SOESi), was synthesized with good yield by an esterification reaction with a previously synthesized 2‐hydroxymethyl‐1,4,6‐trioxaspiro [4,4] nonane (SOEOH) and trimethylsilyl propionic acid. The structure of the new SOESi was confirmed by 1H and 3C NMR. The SOESi and a mixture of DGEBA/SOESi were polymerized with ytterbium triflate as a cationic initiator. The curing was studied with differential scanning calorimetry (DSC) and monitored by Fourier transform infrared (FTIR) spectroscopy. The materials were characterized with DSC, termogravimetric analysis (TGA) and thermodynamomechanical analysis (DMTA). The volume change was evaluated with a Micromeritics gas pycnometer and the flame retardancy was tested by the limiting oxygen index (LOI) measurements. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 4211–4224, 2007

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Catalytic double ring-opening polyaddition of spiro orthoester with acid chloride for shrinkage-controlled molding

Cited by 17 publications

References 16 publications

Expanding Monomers as Anti-Shrinkage Additives

Expanding Monomers as Anti-Shrinkage Additives

Synthesis and properties of polyurethane acrylate modified by different contents of stearyl alcohol

Novel silicon‐containing spiroorthoester to confer combined flame retardancy and low shrinkage properties to epoxy resins

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