Diethyl ketone‐based imine as efficient latent hardener for epoxy resin

Suzuki, Kuniaki; Matsu-Ura, Nobuki; Horii, Hisakazu; Sugita, Yuko; Sanda, Fumio; Endō, Takeshi

doi:10.1002/app.10101

Cited by 19 publications

(20 citation statements)

References 11 publications

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“…Endo et al, developed diethyl ketone-based imines showing fast hydrolysis rate in atmospheric conditions [47,184,185]. They observed that, despite the imine/enamine equilibrium, mixtures with epoxy resins present pot-life larger than 1 month.…”

Section: Page 20 Of 163mentioning

confidence: 97%

“…They observed that, despite the imine/enamine equilibrium, mixtures with epoxy resins present pot-life larger than 1 month. Thanks to their fast hydrolysis rate, these imines are used as hardeners for adhesives [184]. Endo and coworkers also show that it is possible to increase the curing rate of epoxy-imine mixtures by adding five-membered cyclic dithiocarbonates [186,187].…”

Section: Page 20 Of 163mentioning

confidence: 97%

See 1 more Smart Citation

Control of reactions and network structures of epoxy thermosets

Vidil¹,

Tournilhac²,

Musso

et al. 2016

Progress in Polymer Science

298

252

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Recent advances in macromolecular chemistry have revolutionized the way we perceive the synthesis of polymers. Polymerization, to be modern, must be "controlled", which usually means capable of producing macromolecules of well-defined structure. The purpose of this review is to examine how the chemistry of epoxy resins, an almost century-old chemistry, is also involved in this movement. Epoxy resins are characterized by both the flexibility of implementation and the qualities of the polymers obtained. Key materials in health-, mobility-and energy related technologies, these resins are heavily present in high-performance composites, electronic boards, adhesives and coatings. Currently, a large number of resins and hardeners are available on the market or described in the literature and an interesting point is that almost any combination of the two is possible. Common to all these recipes and processes is that a liquid (or soluble) resin at some point becomes insoluble and solid. It is very important to know how to manage this transition, physically known as the gel point, as it is the point after which the shape of the object is irreversibly set. Taking into account the variety of epoxy polymerization processespolyaddition, anionic or cationic polymerization-we detail a number of methods to program the occurrence of the gel point and how this type of control affects the structure of the growing network.

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Section: Page 20 Of 163mentioning

confidence: 97%

Section: Page 20 Of 163mentioning

confidence: 97%

Control of reactions and network structures of epoxy thermosets

Vidil¹,

Tournilhac²,

Musso

et al. 2016

Progress in Polymer Science

298

252

View full text Add to dashboard Cite

show abstract

“…The curing system of imine‐based one‐component epoxy resin is composed of two steps, that is, the first step is the hydrolysis of the imines releasing amines, and the second step is the reaction of the generated amine with epoxides. We have recently reported that diethyl ketone‐based imines show a faster hydrolysis rate than industrially used methyl ethyl ketone‐ and methyl isobutyl ketone‐based imines, and one‐component epoxy resins with diethyl ketone‐based imines show good curing properties and storage stability 4–6. On the other hand, an amine‐epoxide reaction has been reported by many researchers 7–11.…”

Section: Introductionmentioning

confidence: 99%

Role of cyclic dithiocarbonate as a promoter in the reaction of epoxide and imine in the presence of water

Suzuki

Horii

Sugita

et al. 2004

J. Polym. Sci. A Polym. Chem.

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It was demonstrated that the reaction of epoxide and imine as a latent initiator under highly humid conditions was accelerated by addition of 5‐phenoxymethyl‐1,3‐oxathiolane‐2‐thione (1). When 1 was added to a mixture of glycidyl phenyl ether and an imine, the reaction of the epoxide with an amine released from the imine became faster than was the case without 1, that is, 1 worked as a promoter of the reaction. The curing rate and initial adhesive strength of epoxy resin increased compared with that without 1. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 4276–4283, 2004

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“…Imines are hydrolyzed by atmospheric water to release the corresponding amines as the active species. We have recently reported that diethyl ketone–based imines show a faster hydrolysis rate than that of industrially used methyl ethyl ketone– and methyl isobutyl ketone–based imines, and one‐component epoxy resin with the diethyl ketone–based imines shows good curing properties 2–4…”

Section: Introductionmentioning

confidence: 99%

“…Another remaining issue is the brittleness of epoxy resins, although this difficulty can be overcome by use of amines and/or epoxy resin with soft segments such as flexible aliphatic and polyoxyalkylene groups. We previously elucidated the curing of one‐component epoxy resin containing a bifunctional five‐membered cyclic dithiocarbonate (DTC) 5. DTC reacts with an amine to give the corresponding thiourethane compound with a thiol group 6.…”

Section: Introductionmentioning

confidence: 99%

One‐component epoxy resin with imine as water‐initiated latent hardener: Improvement of the mechanical and adhesive properties by the addition of methacrylate copolymer

Suzuki¹,

Sugita²,

Sanda³

et al. 2005

J of Applied Polymer Sci

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ABSTRACT:The effect of addition of methacrylate polymer into a one-component epoxy resin, containing Epikote 828 and diimine as a water-initiated hardener, was examined. Although the cured epoxy resin in the presence of methyl methacrylate-butyl acrylate (MMA-BA) copolymer was very brittle, the resin containing MMA-BA-[␥-(methacryloxy)propyl]trimethoxysilane (TMSMA) copolymer showed good mechanical and adhesive properties. The adhesive strength of the cured epoxy resin containing MMA-BA-TMSMA copolymer was much higher than that without its polymer.

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Diethyl ketone‐based imine as efficient latent hardener for epoxy resin

Cited by 19 publications

References 11 publications

Control of reactions and network structures of epoxy thermosets

Control of reactions and network structures of epoxy thermosets

Role of cyclic dithiocarbonate as a promoter in the reaction of epoxide and imine in the presence of water

One‐component epoxy resin with imine as water‐initiated latent hardener: Improvement of the mechanical and adhesive properties by the addition of methacrylate copolymer

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