Step-growth polymerization of 10,11-epoxyundecanoic acid. Synthesis and properties of a new hydroxy-functionalized thermoplastic polyester

White, Jerry E.; Earls, Jim D.; Sherman, John W.; López, Leonardo C.; Dettloff, Marvin L.

doi:10.1016/j.polymer.2007.05.031

Cited by 25 publications

(20 citation statements)

References 12 publications

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“…For accelerating the polymerization of EOA, initial efforts were focused on screening of a catalyst for the polymerization of EOA. Various catalysts such as tertiary amines, an organometallic compound, and a phosphonium salt that have been demonstrated as effective catalysts for accelerating the reaction between a COOH group and an epoxy group were investigated for the polymerization of EOA (Table ). N ‐Methylmorpholine failed to serve as an effective catalyst for the polymerization of the EOA; only a nonviscous, nonsticky oil was formed after the polymerization at 180°C for 6 h. The ineffective catalysis of N ‐methylmorpholine might be due to its evaporation from the reaction mixture during the polymerization reaction because the boiling point of N ‐methylmorpholine was 113–116°C.…”

Section: Resultsmentioning

confidence: 99%

“…For eliminating the concerns over the low reaction temperature and evaporation of the catalyst, the reaction temperature of 160°C, and dimethylbenzylamine with its boiling point (180°C) being higher than the reaction temperature were investigated and also did not result in substantial polymerization of the EOA (Table ). Tetraphenylphosphonium bromide, an effective catalyst for the step‐growth polymerization of 10,11‐epoxyundecanoic acid that has a terminal epoxy group, was also not an effective catalyst for the polymerization of EOA. CTAA, an organometallic catalyst, effectively and efficiently accelerated the polymerization of EOA, affording a viscous and sticky resin.…”

Section: Resultsmentioning

confidence: 99%

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Development and evaluation of pressure sensitive adhesives from a fatty ester

2014

J of Applied Polymer Sci

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Novel pressure sensitive adhesives (PSAs) were developed from renewable methyl oleate (MO) and fully evaluated for their peel strength, tack force and shear resistance. MO was epoxidized and selectively hydrolyzed on the ester group to form epoxidized oleic acid (EOA) that is a bifunctional monomer containing both a carboxylic acid group and an epoxy group. EOA was step‐growth polymerized to form a hydroxyl‐containing polyester, which was then cured in the presence of a small amount of a polyfunctional epoxide [epoxidized soybean oil or trimethylolpropane triglycidyl ether (TMPTGE)] to afford PSAs. The PSAs from the polyester cured with TMPTGE exhibited high peel strength (2.4 N/10 mm), high tack force (5.8 N), and sufficient shear resistance (9.0 min). The PSAs can be fully based on renewable natural materials, and their preparations are environmentally friendly. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41143.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Development and evaluation of pressure sensitive adhesives from a fatty ester

2014

J of Applied Polymer Sci

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“…27. Among classical efficient base catalysts are: (i) imidazoles [142][143][144], (ii) tertiary amines [138,145,146], (iii) phosphonium bromide [140,147] and (iv) some metal salts [80][81][82]. For instance, 1,2-dimethylimidazole [142] and dimethylbenzylamine [145] as well as tetrabutylphosphonium bromide [140] and zinc acetate [82] have been reported as very efficient catalysts (Fig.…”

Section: Carboxylic Acidsmentioning

confidence: 99%

Control of reactions and network structures of epoxy thermosets

Vidil¹,

Tournilhac²,

Musso

et al. 2016

Progress in Polymer Science

299

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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“…[61,62,63] Polycondensation of 10,11-epoxyundecanoic acid (EUA) 74 initiated by tetraphenylphosphonium bromide (TPPB) in propylene glycol monomethyl ether acetate (PMA) results in a white fibrous solid 86 (Scheme 21). [96] The mechanism of initiation by TPPB occurs through haloalkoxide formation and subsequent abstraction of a proton from 10,11-EUA which initiates the polymerization. The halohydrin formed during initiation takes part in the polymerization through direct substitution of the bromide by a 10,11-epoxyundecanoic acetate anion or through the formation of an epoxide by intramolecular substitution.…”

Section: Polyamides and Polyestersmentioning

confidence: 99%

Undecylenic Acid: A Valuable and Physiologically Active Renewable Building Block from Castor Oil

2009

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A lot of attention is currently being paid to the transition to a biobased economy. In this movement, most efforts concentrate on the development of bioenergy applications including bioethanol, biodiesel, thermochemical conversion of biomass, and others. However, in the energy sector other nonbiomass alternatives are known, whereas no valuable alternatives are available when thinking about chemical building blocks. Therefore, it is also essential to develop new routes for the synthesis of bio-based chemicals and materials derived thereof. Such intermediates can originate either from plants or from animals. Castor oil is a non-edible oil extracted from the seeds of the castor bean plant Ricinus communis (Euphorbiaceae), which grows in tropical and subtropical areas. Globally, around one million tons of castor seeds are produced every year, the leading producing areas being India, PR China, and Brazil.2 10-Undecenoic acid or undecylenic acid is a fatty acid derived from castor oil that, owing to its bifunctional nature, has many possibilities to develop sustainable applications.

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Step-growth polymerization of 10,11-epoxyundecanoic acid. Synthesis and properties of a new hydroxy-functionalized thermoplastic polyester

Cited by 25 publications

References 12 publications

Development and evaluation of pressure sensitive adhesives from a fatty ester

Development and evaluation of pressure sensitive adhesives from a fatty ester

Control of reactions and network structures of epoxy thermosets

Undecylenic Acid: A Valuable and Physiologically Active Renewable Building Block from Castor Oil

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