Preparation of Polyamines by the Michael Reaction

Yoda, Kentaro; Toda, Takao

doi:10.1246/bcsj.41.2519

Cited by 8 publications

(5 citation statements)

References 4 publications

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“…In a similar manner Klee et al obtained branched methacrylates by addition of ethylene glycol acrylate methacrylate to diamines and studied their application in dental composites . An early work from Yoda and Toda described the addition polymerization of different bisacrylates with amines leading to linear polyamines …”

Section: Introductionmentioning

confidence: 99%

“…In a similar 20 An early work from Yoda and Toda described the addition polymerization of different bisacrylates with amines leading to linear polyamines. 21 In this paper, we would like to report the synthesis of a series of novel, branched bismethacrylate hybrid monomers as well as macromonomers with pendant alkoxysilane moieties, prepared via convenient Michael addition of R,ω-alkoxysilane-amines to acrylate-methacrylates. Our investigation focuses on the relationship between molecular structure and viscosity and volume shrinkage as well as mechanical properties of the respective composites.…”

Section: Introductionmentioning

confidence: 99%

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Bismethacrylate-Based Hybrid Monomers via Michael-Addition Reactions

Müh¹,

Marquardt²,

Klee³

et al. 2001

Macromolecules

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Bismethacrylate monomers and macromonomers bearing various alkoxysilyl units were prepared by convenient Michael addition of ethylene glycol acrylate methacrylate (EGAMA) and ethylene glycol bisacrylate (EGBA) to various α,ω-alkoxysilylamines. The resulting monomers and macromonomers have been characterized in detail by NMR spectroscopy, VPO measurements and FAB−MS. Average molecular weights M n ranged between 530 and 1600 (VPO) in addition reactions with bisacrylates. FAB−MS evidenced the formation of a homologous macromonomer series. Viscosities of the liquid monomers are relatively low, ranging from 52 to 305 mPa·s. This renders these compounds interesting as reactive diluents in dental composite formulations. Polymerization of the monomers and macromonomers resulted in low volumetric shrinkage in the range of ΔV = 2.2−7.8% at high methacrylate conversion. Cross-linking was monitored by photo-DSC. Furthermore, composites were prepared by mixing Bis-GMA with the new hybrid monomers, initiator and glass filler. The composites showed compressive strengths of 190−329 MPa, flexural strengths from 23 to 53 MPa and Young's moduli between 2090 and 5060 MPa. Low volumetric shrinkage was observed also for the composites upon photopolymerization, ranging from only 0.8% to 2.2% in comparison to over 3% shrinkage of commercially available composites. Besides the viscosity reducing effect due to the branched structure, the pendant alkoxysilyl groups of the synthesized hybrid monomers can be polymerized to form nanoparticles with reactive acrylate surface, permitting the in situ preparation of nanocomposites.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bismethacrylate-Based Hybrid Monomers via Michael-Addition Reactions

Müh¹,

Marquardt²,

Klee³

et al. 2001

Macromolecules

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“…14,16 While recent focus on PBAEs has been in crosslinked materials for biomedical applications, they have in fact been studied by a variety of research groups. The earliest publication was from 1968 by Yoda and Toda, 18 who described the production of a PBAE from piperazine or trans-2,5-dimethylpiperazine and divinyl sulfone. A short time later, Danusso and Ferruti 19 examined many options of reacting amines with vinyl groups, as well as acrylic diesters.…”

Section: Introductionmentioning

confidence: 99%

Swelling and degradation of hydrogels synthesized with degradable poly(β-amino ester) crosslinkers

McBath

Shipp

2010

Polym. Chem.

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The synthesis of diacrylated poly(b-amino ester) crosslinkers, obtained from the oligomerization of di(ethylene glycol) diacrylate (DEGDA) and piperazine (PIPz), and their use in hydrogels are reported. In particular, the poly(b-amino ester) crosslinkers were used to study swelling and degradation properties of hydrogels made of N-vinylpyrrolidone and 2-hydroxy ethyl methacrylate. Poly(b-amino ester) crosslinkers with two different molecular weights (800 and 3000 g mol À1 ) and hydrogels with 1 and 3% crosslinker were studied. Swelling and degradation of the gels were monitored in phosphate buffered saline (pH ¼ 7.4) at 37 C. The swelling and degradation characteristics of the poly(b-amino ester) crosslinked hydrogels were then compared to hydrogels crosslinked with poly(ethylene glycol) diacrylate (PEGDA) of similar molecular weights. It was found that both swelling and degradation were faster in the poly(b-amino ester) crosslinked hydrogels, particularly for the highest molecular weight poly(b-amino ester) crosslinker.

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“…The Michael addition of amines containing an active hydrogen to activated double bonds like acrylates can be exploited to prepare telechelic macromonomers or polymers. Already in 1968 Yoda and Toda [1] reported on polyamines that are formed by the addition reaction of diacrylates and piperazine. Recently, this reaction type was applied for the modification of poly (propyleneimine) dendrimers with 2-methacryloyloxyethyl acrylate by Moszner et al [2] The formation of branched methacrylates was reported by Klee et al [3] The latter monomers were studied with regard to their applicability as matrix resins for dental composites.…”

Section: Introductionmentioning

confidence: 99%