Stereochemical Control in the Anionic Polymerization of β-Butyrolactone Initiated with Alkali-Metal Alkoxides

Jedliński, Zbigniew; Kowalczuk, Marek; Kurcok, Piotr; Adamus, Grażyna; Matuszowicz, Andrzej; Sikorska, Wanda; Gross, Richard A.; Xu, Jin; Lenz, Robert W.

doi:10.1021/ma951888s

Cited by 75 publications

(59 citation statements)

References 31 publications

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“…Chemical synthesis of racemic [16][17][18][19] and chiral 20,21 poly(3-hydroxybutanoic acid) from b-butyrolactone monomer has been reported by some of us previously. Polymers thus obtained were characterized by 1 H and 13 C NMR, gel permeation chromatography, Fourier transform infrared spectroscopy and chemical analysis.…”

Section: Resultsmentioning

confidence: 97%

Electrospray tandem mass spectrometry of poly(3-hydroxybutanoic acid) end groups analysis and fragmentation mechanism

Jedliński

Adamus

Kowalczuk

et al. 1998

Rapid Commun. Mass Spectrom.

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The electrospray ionization tandem mass spectrometry technique applied for the first time to aliphatic polyester analysis, allowed fast and reliable identification of the various macromolecules of poly(3-hydroxybutanoic acid) (PHB), synthesized via ring-opening polymerization of b-butyrolactone. It was demonstrated that the biomimetic polymers studied contain various end groups, depending on the anionic initiator employed, and show close similarity to the natural PHB produced by enzymes in living cells of prokaryotic and eukaryotic organisms. #

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Section: Resultsmentioning

confidence: 97%

Electrospray tandem mass spectrometry of poly(3-hydroxybutanoic acid) end groups analysis and fragmentation mechanism

Jedliński

Adamus

Kowalczuk

et al. 1998

Rapid Commun. Mass Spectrom.

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“…Therefore, several attempts to use a catalyst based on much less toxic metal compounds are being undertaken [2,6,11,[22][23][24][25][26][27]. The anionic polymerization of β-butyrolactone had been widely studied [27][28][29][30][31][32][33][34][35][36][37][38][39][40], and in general polymers with low molecular weight were obtained. Relatively low toxic alkali metal hydrides are among the initiators used for this purpose [27], nevertheless, they have not been used so far for the synthesis of copolymers of (R,S)-BL and CL.…”

Section: Introductionmentioning

confidence: 99%

Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

Monsalve¹,

Contreras²,

Laredo³

et al. 2010

Express Polym. Lett.

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Abstract. Copolymers of racemic β-butyrolactone ((R,S)-BL) and ε-caprolactone (CL), were synthesized by ring-opening polymerization initiated by sodium hydride (NaH). The initiator exhibited a satisfactory catalytic activity, producing copolymers whose yields are greatly influenced by the feed monomer ratio, CL/BL. All polymers obtained were characterized by nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and wide angle X-rays scattering, WAXS. The molar composition of copolyesters determined by 1 H-NMR spectra, showed that the incorporation of CL is favoured over the incorporation of (R,S)-BL. Gel permeation chromatography and 13 C-NMR spectra indicated that CL/BL copolymers had block sequence distribution. The TGA analysis of copolymers showed that these copolymers are stable up to temperatures near 200°C, followed by a decomposition process in two steps; the first one is attributed to the (R,S)-BL block degradation and the second to the remaining PCL block. The crystallization process of these copolymers was studied by DSC and WAXS showing that the amorphous (R,S)-BL segments chains did not affect the crystallinity of the PCL blocks.

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“…In contrast to coordination-insertion mechanism [16][17][18], the spectroscopic data suggest that the nucleophile -OR 0 ion of hybrid material attacks C=O carbon atom in e-CL. As it can be seen from literature survey for the base catalysts [19][20][21][22][23], this is an anionic mechanism.…”

Section: Resultsmentioning

confidence: 99%

Preparation, Characterization and Application of Hybrid Materials Having Multifunctional Properties

Kayan

2015

J Inorg Organomet Polym

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Inorganic-organic hybrid materials were prepared in two steps by the sol gel process. In the first step, new hybrid material, Al(OBu s ) 3 -GPTS-hydrolyzate, was prepared from the hydrolysis of the mixture of aluminum secondary butoxide (Al(OBu s ) 3 ) and 3-glycidyloxypropyltrimethoxysilane (GPTS) in 1:1 mol ratio. The hydrolysis reaction was carried out with 0.1 molar HCl in 50 ml of butanol. In the second step, hydrolyzate hybrid material reacted with KOH, KOBu t , and NaOSiMe 3 in 1:1 mol ratio at room temperature for 24 h. After these stages, hybrid materials were washed, dried and characterized by a combination of elemental analysis, Brunauer-EmmettTeller analysis, Barrett-Joyner-Halenda analysis, powder X-ray diffraction, scanning electron microscope, energy dispersive X-ray, and Fourier transform infrared spectroscopies. These hybrid materials were used in the polymerization of e-caprolactone (e-CL) in order to see the activity of hybrid materials as catalysts. This study showed that hybrid materials were effective catalyst in e-CL polymerization.

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Stereochemical Control in the Anionic Polymerization of β-Butyrolactone Initiated with Alkali-Metal Alkoxides

Cited by 75 publications

References 31 publications

Electrospray tandem mass spectrometry of poly(3-hydroxybutanoic acid) end groups analysis and fragmentation mechanism

Electrospray tandem mass spectrometry of poly(3-hydroxybutanoic acid) end groups analysis and fragmentation mechanism

Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

Preparation, Characterization and Application of Hybrid Materials Having Multifunctional Properties

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