Polymerization of cyclic imino ethers. II. Oxazines

Levy, Avishai; Litt, Morton H.

doi:10.1002/pol.1967.110050928

Cited by 72 publications

(48 citation statements)

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“…The polymerization was stopped by adding an excess of sodium azide and kept at 80 8C during 24 h. The polymer was purified by precipitation in diethyl ether, then dried under vacuum. 1 3.42 (ÀNÀCH 2 ÀCH 2 ÀNÀ).…”

Section: Synthesis Of Azido-poxzmentioning

confidence: 99%

“…[1][2][3][4] Poly(2-oxazoline)-based compounds have interesting properties in the field of biomedical applications. [5] Our interest has focused on poly(2-methyl-2-oxazoline) (POXZ), which is a hydrophilic and non-ionic polymer showing properties such as biocompatibility and lack of toxicity as evidenced by early studies in relation to the biomedical applications.…”

Section: Introductionmentioning

confidence: 99%

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Click‐Chemistry: An Alternative Way to Functionalize Poly(2‐methyl‐2‐oxazoline)

Volet

Lav

Babinot

et al. 2010

Macro Chemistry & Physics

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CROP has been used to synthesize well‐defined POXZ with a monofunctional (iodomethane) or a bifunctional (1,3‐diiodopropane) initiator. POXZ has been functionalized with an azido group at one (α‐azido‐POXZ, $\overline {M} _{{\rm n}} $ = 3.58 × 103 g · mol−1) or both ends (α,ω‐azido‐POXZ, $\overline {M} _{{\rm n}} $ = 6.21 × 103 g · mol−1) of the macromolecular chain. The Huisgen 1,3‐dipolar cycloaddition has been investigated between azido‐POXZ and a terminal alkyne on a small or larger molecule (PEG). In each case, the click reaction has been successful and quantitative. In this way, different telechelic polymers (polymers bearing different functions such as acrylate, epoxide, or carboxylic acid) and block copolymers of POXZ and PEG have been prepared. The polymers have been characterized by means of FTIR, 1H NMR, and SEC. magnified image

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Section: Synthesis Of Azido-poxzmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Click‐Chemistry: An Alternative Way to Functionalize Poly(2‐methyl‐2‐oxazoline)

Volet

Lav

Babinot

et al. 2010

Macro Chemistry & Physics

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“…The cationic ring-opening polymerization of 2-substituted-2-oxazolines has been intensively studied since the mid sixties by several groups. [4][5][6][7] It is known, for example, that the polymerization of 2-phenyl-2-oxazoline takes place by treating the monomer with strong electrophiles (e.g., methyl tosylate) to generate poly(N-benzoylethylenimine) (Scheme 1). Recent research investigated the effect of temperature on the polymerization of 2-phenyl-2-oxazoline with methyl tosylate under conventional heating.…”

Section: Introductionmentioning

confidence: 99%

Microwave Accelerated Polymerization of 2‐Phenyl‐2‐oxazoline

Sinnwell

Ritter

2005

Macromol. Rapid Commun.

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Summary: We studied the cationic ring‐opening polymerization of 2‐phenyl‐2‐oxazoline under microwave irradiation. A comparison with thermal heating shows a great enhancement in the reaction rates while the living character of the polymerization is conserved. The polymerizations were performed at the temperature of boiling butyronitrile (123 °C). The polymerization of 2‐phenyl‐2‐oxazoline under microwave conditions, described herein for the first time, is shown to be a rapid and environmentally friendly alternative to the classical methods.Schematic of the activation of the reactive site by microwave irradiation.imageSchematic of the activation of the reactive site by microwave irradiation.

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“…In addition, the increased number of methylene units in the main-chain will change the physical properties of such polymers compared to P-2-OZO while the 2-substituent can still be used to further tune the polymer properties. Even though the first report on the CROP of 2-OZI appeared shortly after the first 2-OZO reports, [11] the P-2-OZI received much less attention than P-2-OZO. P-2-OZO can also be substituted on the 4th or 5th position, which introduces a chiral group in the polymer main-chain.…”

Section: Introductionmentioning

confidence: 93%

“…The synthesis of a series of P-2-substituted-2-OZI ( Figure 1) was already reported in 1967 by Litt and coworkers, shortly after the first reports on P-2-OZO. [11] The glass transition temperature (T g ) ( Table 1) of P-2-OZI is about 30-50 8C lower than the T g of the corresponding P-2-OZO due to the increased chain flexibility resulting from the additional methylene unit in the main chain. Saegusa and coworkers synthesized P-2-unsubstituted-2-OZI, [16] which is a semi-crystalline white solid with a melting point of %120 8C.…”

Section: Crop Of 2-oxazinesmentioning

confidence: 99%

Poly(cyclic imino ether)s Beyond 2‐Substituted‐2‐oxazolines

Bloksma

Schubert

Hoogenboom

2011

Macromol. Rapid Commun.

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2-Oxazolines (2-OZO) are 5-membered cyclic imino ethers whose cationic ring-opening polymerization (CROP) mechanism and resulting polymer properties are extensively studied. However, also 6- and 7-membered cyclic imino ethers can be polymerized via CROP. Together with the much less studied 4- and 5-substituted main-chain chiral poly(2-oxazoline)s (P-2-OZO), these compounds are interesting monomers to enhance the versatility of (co)poly(cyclic imino ether)s. To emphasize the potential of such alternative cyclic imino ether monomers, we provide an overview on the polymerizations of 2-oxazine (2-OZI) and chiral 4- and 5-substituted 2-OZO as well as of selected properties of the resulting polymers. In addition, the hydrolysis of these polymers into the corresponding poly(alkylene imine)s will be addressed.

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Polymerization of cyclic imino ethers. II. Oxazines

Cited by 72 publications

References 1 publication

Click‐Chemistry: An Alternative Way to Functionalize Poly(2‐methyl‐2‐oxazoline)

Click‐Chemistry: An Alternative Way to Functionalize Poly(2‐methyl‐2‐oxazoline)

Microwave Accelerated Polymerization of 2‐Phenyl‐2‐oxazoline

Poly(cyclic imino ether)s Beyond 2‐Substituted‐2‐oxazolines

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