Amine-Manganese Complex as an Efficient Catalyst for Polyurethane Syntheses

Inoue, Shin‐ichi; Nagai, Yasutaka; Okamoto, Hiroshi

doi:10.1295/polymj.34.298

Cited by 14 publications

(13 citation statements)

References 16 publications

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“…When Zr(acac) 4 –triethylamine system is used, its catalytic activity is comparable with that of dibutyltin diacetate . Polymerization reaction of hexamethylene diisocyanate with diethylene glycol can be catalyzed by M(acac) 2 –triethylenediamine system (M = Mn, Fe, Co, Ni, and Cu) and Mn(acac) 2 –triethylenediamine system has comparable catalytic activity with that of DBTDL.…”

Section: Introductionmentioning

confidence: 99%

“…To solve this problem, the catalysts having slightly lower reactivity than Cu(OAc) 2 (en) 2 were prepared. As amine is known to act as cocatalyst for M(acac) 2 in the reaction between hexamethylene diisocyanate and diethylene glycol to give polyurethane, we were interested to synthesize metal acetylacetonate–amine and metal nitrate–amine complexes from the reaction between metal salts and aliphatic amines. The metal salts used were Cu(acac) 2 , Zn(acac)2, and Cu(NO 3 ) 2 .…”

Section: Introductionmentioning

confidence: 99%

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Metal acetylacetonate–amine and metal nitrate–amine complexes as low‐emission catalysts for rigid polyurethane foam preparation

Sridaeng

Limsirinawa

Sirojpornphasut

et al. 2015

J of Applied Polymer Sci

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Six metal-amine complexes, Cu(acac) 2 (trien), Zn(acac) 2 (en), Zn(acac) 2 (trien), Cu(NO 3 ) 2 (en) 2 , Cu(NO 3 ) 2 (trien), and Cu(NO 3 ) 2 (tetraen), are synthesized from metal acetylacetonates [M(acac) 2 , where M 5 Cu and Zn] or metal nitrate [M(NO 3 ) 2 , where M 5 Cu] and aliphatic amines (en 5 ethylenediamine, trien 5 triethylenetetramine, and tetraen 5 tetraethylenepentamine). These metal-amine complexes can be used as catalysts in the preparation of rigid polyurethane (RPUR) foams. All metal-amine complexes emit very weak odor when compared with N,N-dimethylcyclohexylamine (DMCHA), which is a commercial catalyst commonly used in the preparation of RPUR foams. DMCHA emits very strong amine odor that affects working environment in RPUR foam processing. Among all metal complexes, Cu(acac) 2 (trien) has the highest catalytic activity. In comparison with DMCHA, Cu(acac) 2 (trien) shows slightly higher catalytic activity in gelling reaction but lower catalytic activity in blowing reaction. RPUR foam prepared from Cu(acac) 2 (trien) has lower density and compressive strength than that prepared from DMCHA. V C 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42332.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metal acetylacetonate–amine and metal nitrate–amine complexes as low‐emission catalysts for rigid polyurethane foam preparation

Sridaeng

Limsirinawa

Sirojpornphasut

et al. 2015

J of Applied Polymer Sci

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“…Besides amines, metal compounds and metal complexes can be used as catalysts in the preparation of polyurethane and waterborne polyurethane (8)(9)(10)(11)(12)(13). Our research group synthesized new catalysts with good catalytic activity for the preparation of water-blown rigid polyurethane (RPUR) foams (14).…”

Section: Introductionmentioning

confidence: 99%

Copper-amine complex solution as a low-emission catalyst for flexible polyurethane foam preparation

et al. 2015

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A low-emission catalyst for the preparation of flexible polyurethane (FPUR) foams was developed. Copper-amine complex solutions in ethylene glycol (EG), namely, Cu(OAc) 2 (en) 2 -EG and Cu(OAc) 2 (trien)-EG (en, ethylenediamine; trien, triethylenetetramine), were synthesized and used as catalysts for the preparation of FPUR foams. The synthesis of Cu(OAc) 2 (en) 2 -EG and Cu(OAc) 2 (trien)-EG is convenient because the synthesis of copper-amine complexes can be done in situ using ethylene glycol as a solvent and no purification step is needed. It was found that Cu(OAc) 2 (en) 2 -EG was a suitable catalyst for FPUR foam preparation. In comparison to Dabco EG (or triethylenediamine), which is a commercial catalyst for FPUR foam preparation, Cu(OAc) 2 (en) 2 -EG had a comparable catalytic activity in gelling reaction and a higher catalytic activity in blowing reaction. The FPUR foam prepared from Cu(OAc) 2 (en) 2 -EG had a lower density than that prepared from Dabco EG.

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“…8 Other catalysts used for polyurethane formation have been metal complexes based on bismuth, zirconium, zinc, titanium, iron, and aluminum. [9][10][11][12] Copper(II)-amine complexes have been used as catalysts in the oxidative polymerization of phenol derivatives, [13][14][15][16] hydrolysis of organophosphate esters, 17 O-arylation reaction of phenols, 18 and epoxidation reaction. 19 For nickel(II)-amine complexes, they were employed as a catalyst for enecarbamate additions to butane-2,3-dione 20 and as a catalyst for alkane hydroxylation with meta-chloroperoxybenzoic acid (m-CPBA).…”

Section: Introductionmentioning

confidence: 99%

Copper–amine complexes as new catalysts for rigid polyurethane foam preparations

Pengjam¹,

Saengfak²,

Ekgasit³

et al. 2011

J of Applied Polymer Sci

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A new class of catalyst for the preparation of rigid polyurethane (RPUR) foams was developed. Metal(II)-amine complexes [M(en) 2 and M(trien), where M ¼ Cu or Ni, en ¼ ethylenediamine, and trien ¼ triethylenetetramine] were synthesized and used as catalysts in the preparation of RPUR foams. The catalytic activity of the metal(II)-amine complexes and properties of the RPUR foams were investigated and compared to those prepared by N,N-dimethylcyclohexylamine (DMCHA), which is a common commercial tertiary amine catalyst used in the preparation of RPUR foams. The use of M(en) 2 and M(trien) can improve the working environment in RPUR foam processing because DMCHA and other commercial tertiary amine catalysts have a strong odor, whereas M(en) 2 and M(trien) do not have any odor. The reaction times in RPUR foam preparation, namely, cream time, gel time, tack-free time, and rise time, were investigated. These data indicated that the copper-ethylenediamine complex [Cu(en) 2 ] and copper-triethylenetetramine complex [Cu(trien)] had comparable catalytic activity to DMCHA, whereas the catalytic activity of the nickel complexes was not good. Attenuated total reflection-IR spectroscopy of the RPUR foams prepared with Cu(en) 2 and Cu(trien) showed quantitative isocyanate (NCO) conversion. The density and compressive strength of the RPUR foams prepared from Cu(en) 2 and Cu(trien) were comparable to those prepared from DMCHA.

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Amine-Manganese Complex as an Efficient Catalyst for Polyurethane Syntheses

Cited by 14 publications

References 16 publications

Metal acetylacetonate–amine and metal nitrate–amine complexes as low‐emission catalysts for rigid polyurethane foam preparation

Metal acetylacetonate–amine and metal nitrate–amine complexes as low‐emission catalysts for rigid polyurethane foam preparation

Copper-amine complex solution as a low-emission catalyst for flexible polyurethane foam preparation

Copper–amine complexes as new catalysts for rigid polyurethane foam preparations

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