Study on the synthesis of urethane oligomers as intermediate products for the production of linear polyurethanes

Król, Piotr; Pilch‐Pitera, Barbara

doi:10.1016/s0014-3057(00)00116-6

Cited by 23 publications

(22 citation statements)

References 16 publications

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“…[7][8][9][10] TDI is widely used with a variety of polyol compounds, such as ethylene glycol, diethylene glycol, trimethylpropanol, and water, to produce TDI prepolymers. Especially, the polymerization reaction of TDI with water, under conditions supplying a proper amount of water, has been widely used for the production of polyurea resin.…”

Section: Introductionmentioning

confidence: 99%

Reaction Monitoring of Toluenediisocyanate (TDI) Polymerization on a Non-Mixable Aqueous Surface by MALDI Mass Spectrometry

Ahn

Kim

2013

ANAL. SCI.

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The polymerization reaction of toluene diisocyanate (TDI) and hydroxyl compounds has been widely used for the production of polyurea resins. Since the composition and molecular-weight distribution of polymer adducts greatly influence the final properties of the resuting polymer, the development of analytical tools capable of monitoring the polyaddition reactions is important to control them as well as the properties of the resuting polymer. Here we report that matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI TOF MS) is useful to precisely monitor time-dependent dynamic events occurring in the polymerization reaction of TDI with water. For this purpose, the polymerization reactions were conducted in two different reaction systems, continuously supplying sufficient water and depleting water after an initial exposure of water to provide an anhydrous storage condition of prepolymer adducts. Samples prepared in a time course from the two different reaction systems were analyzed by a MALDI TOF mass spectrometer. The polymerization adducts of TDI and water were monitored and showed to consist of three structural types of polymer adduct series, including diisocyanate, monoamino, and diamino series. These MALDI mass data efficiently reflected changes in the reaction conditions of each TDI polymerization reaction, thereby providing precise information at the molecular level for time-dependent events occurring during the polymerization reaction. These events included changes between the polymer adduct series and in the molecular-weight distribution of each polymer adduct series. The results obtained in this study suggest that high-throughput MALDI MS-based dynamic monitoring of polymerization can be used to precisely control the polymerization reaction as well as to rapidly monitor the state of prepolymers in storage.

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Section: Introductionmentioning

confidence: 99%

Reaction Monitoring of Toluenediisocyanate (TDI) Polymerization on a Non-Mixable Aqueous Surface by MALDI Mass Spectrometry

Ahn

Kim

2013

ANAL. SCI.

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“…These reactions affect the molar mass distribution and final product properties such as curing dynamics and mechanical properties of segmented polyurethane in various ways [17,18]. The chemical structure of polyurethane prepolymer has been extensively studied by several techniques such as gel permeation chromatography (GPC) [19][20][21][22][23], nuclear magnetic resonance (NMR) spectroscopy [14,24,25] and mass spectrometry (MS) [26][27][28]. It is essential to thoroughly investigate the mechanism of urethane reactions and other side reactions to control the properties of the resulting polyurethane products, and most importantly, to obtain polyurethane prepolymer which could be purified through the thin film evaporator.…”

Section: Introductionmentioning

confidence: 99%

Structural investigations of toluene diisocyanate (TDI) and trimethylolpropane (TMP)-based polyurethane prepolymer

Zhang

et al. 2012

Journal of Industrial and Engineering Chemistry

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“…For example, to produce flexible foams, toluene diisocyanate (TDI) is the most commonly used isocyanate component . Moreover, the TDI used in the industry is a blend of the 2,4‐ and 2,6‐isomers, generally in an 80/20 ratio (TDI‐80), respectively ,. Furthermore, the diisocyanate structure is well known to greatly affect the mechanical performance of the resulting PUs .…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, due to difference in the reactivity of the 2,4‐ and 2,6‐isomers, the catalyst concentration needs to increased when blends with a higher 2,6‐isomer content are used in order to overcome the 2,6‐isomer having a lower reactivity than the 2,4‐isomer . Since the reactivity of the different TDI isomers plays an important role in many PU formulations, the reaction of the pure 2,4‐TDI isomer and that of the TDI‐80 blend with various alcohols are well‐documented ,. Surprisingly, however, despite its importance, studies on the kinetics of the pure 2,6‐TDI isomer with alcohols are very scarce and limited to its kinetics with 1‐butanol only .…”

Section: Introductionmentioning

confidence: 99%

Reactions of 2,6‐Toluene Diisocyanate with Alcohols: Kinetic Studies in the Absence and Presence of Catalysts

Nagy

Kuki

et al. 2017

ChemistrySelect

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The kinetics of the reaction between 2,6‐toluene diisocyanate (2,6‐TDI) and alcohols with varying carbon chain lengths and a primary or secondary hydroxyl group in the absence and presence of tin(II) 2‐ethylhexanoate (TEH) as a catalyst were studied. The alcohols were applied in high molar excess relative to 2,6‐TDI to obtain a pseudo‐first‐order dependence on 2,6‐TDI. Based on the kinetic results, it was found that (i) 2,6‐TDI reacts faster with alcohols with longer carbon chains than those with shorter ones, (ii) secondary alcohols are approximately 3 times less reactive towards 2,6‐TDI than primary ones, and (iii) after the first isocyanate group has been reacted, the reactivity of the remaining isocyanate group decreases. Furthermore, the rate constants were found to depend linearly on catalyst concentration.

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Study on the synthesis of urethane oligomers as intermediate products for the production of linear polyurethanes

Cited by 23 publications

References 16 publications

Reaction Monitoring of Toluenediisocyanate (TDI) Polymerization on a Non-Mixable Aqueous Surface by MALDI Mass Spectrometry

Reaction Monitoring of Toluenediisocyanate (TDI) Polymerization on a Non-Mixable Aqueous Surface by MALDI Mass Spectrometry

Structural investigations of toluene diisocyanate (TDI) and trimethylolpropane (TMP)-based polyurethane prepolymer

Reactions of 2,6‐Toluene Diisocyanate with Alcohols: Kinetic Studies in the Absence and Presence of Catalysts

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