Poly(urethane-urea)s Based on Oligocarbonatediols Comprising Bis(carbamate)alkanes

Pawłowski, P.; Szymański, Adam; Kozakiewicz, Janusz; Przybylski, Jarosław; Rokicki, Gabriel

doi:10.1295/polymj.37.742

Cited by 17 publications

(13 citation statements)

References 21 publications

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“…Taking into account that in the reaction of trimethylene bis(methyl carbonate) with 1,3‐propanediol cyclic carbonate trimethyl carbonate can be in parallel formed, oligo(trimethylene carbonate) diol was obtained by ring‐opening polymerization of TMC using 1,3‐propanediol as an initiator without use of any catalyst …”

Section: Resultsmentioning

confidence: 99%

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Mazurek

Tomczyk

Auguścik

et al. 2014

Polymers for Advanced Techs

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a Poly(carbonate-urethane-urea)s (PCUU) based on oligocarbonate diols (M n ≈ 2000) with different length of the hydrocarbon chain as soft segments were synthesized and investigated. Carbonate oligomerols were obtained in a two-step method from dimethyl carbonate (DMC) and linear α,ω-diols (1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,9-nonanediol, 1,10-dekanediol and 1,12-dodecanediol). Oligo(trimethylene carbonate) diol was synthesized using ring-opening polymerization of trimethylence carbonate. PCUUs were obtained by prepolymer method using isophorone diisocyanate (IPDI) and water as a chain extender. Changes in polymers properties with increase of methylene group number between carbonate linkages were investigated by differential scanning calorimetry (DSC), dynamic mechanical thermal analysis (DMTA), tensile strength and hardness measurements. The thermal stability was also analyzed by means of thermogravimetric analysis (TGA). Based on FTIR analysis influence of methylene groups number between carbonate linkages on phase separation and concentration of allophanate and biuret groups in the samples were investigated. The obtained poly(carbonate-urethane-urea)s exhibited very good mechanical properties. Tensile strength and elongation at break were 40 MPa and 400-600%, respectively, depending on the oligocarbonate used.

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Section: Resultsmentioning

confidence: 99%

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Mazurek

Tomczyk

Auguścik

et al. 2014

Polymers for Advanced Techs

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“…This results from the fact that the hydrolysis of carbonate linkages does not produce the acidic groups that catalyze the hydrolytic degradation of ester bonds. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] Aliphatic PES or PCs are usually synthesized by the ringopening polymerization (ROP) of cyclic monomers in the presence of coordination catalysts (e.g., Zn, Al, Sn compounds). Furthermore, the commercial biomedical PURs are usually prepared by the polyaddition process catalyzed by organic-metal compounds (mainly Sn).…”

Section: Introductionmentioning

confidence: 99%

Segmented polyurethane elastomers derived from aliphatic polycarbonate and poly(ester‐carbonate) soft segments for biomedical applications

Sobczak

Dębek

Olędzka

et al. 2012

J. Polym. Sci. A Polym. Chem.

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A series of biomedical polyurethane elastomers (PURs) based on poly(ester‐carbonate)s (PECs) and polycarbonates (PCs) were synthesized and spectrally characterized fully. PEC or PC diols were synthesized by the ring‐opening polymerization of ε‐caprolactone, trimethylene carbonate, and neopentyl carbonate catalyzed by lipase from Candida antarctica. PURs were prepared by free‐metal method from PEC or PC diols and 4,4′‐methylenebis(phenyl isocyanate), with 1,4‐butanediol as a chain extender. The physical and mechanical properties as well as hydrolytic stability of the obtained PURs were determined. The toxicity of the received polymers was evaluated using bacterial luminescence test and two protozoans assays. The presented preliminary studies suggest that PEC or PC diols prepared in this way might be applied for the synthesis of biomedical PURs with improved hydrolytic stability. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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“…As it was discussed in our earlier article, high molar excess of propylene carbonate suppresses the formation of linear carbonate linkages . In this case, almost all molecules were terminated with 2‐hydroxypropylcarbonate groups and there was no transesterification reaction leading to the formation of 1 and 1,2‐propylene glycol due to the thermodynamic reason (Scheme ).…”

Section: Resultsmentioning

confidence: 57%

“…Due to the presence of carbonate linkages in the main chains, they exhibit much higher hydrolytic resistance in comparison to ester oligomerols and oxidative resistance in comparison to ether oligomerols . Moreover, polyurethanes based on oligocarbonate diols exhibit excellent mechanical properties such as high tensile strength (40 MPa) and high elongation at break (400%) …”

Section: Introductionmentioning

confidence: 99%

Propylene carbonate as a source of carbonate units in the synthesis of elastomeric poly(carbonate–urethane)s and poly(ester–carbonate–urethane)s

Mazurek

Parzuchowski

Rokicki

2013

J of Applied Polymer Sci

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The synthesis of oligocarbonate diols from propylene carbonate (PC) and α,ω‐diols with hydrocarbon chain of various length is presented and discussed. Syntheses with different catalysts and molar ratio of the reactants were performed. Novel method of the synthesis of oligo(ester–carbonate) diols based on PC, dimethyl succinate, adipate or terephthalate, and α,ω‐diols was investigated. The resultant oligomerols did not contain any oxy‐1,2‐propylene fragments as well as other ether units in their chemical structure. Based on the obtained oligocarbonate and oligo(ester–carbonate) diols, polyurethanes were obtained according to the prepolymer method using isophorone and hexamethylene diisocyanate and water as a chain extender. The obtained products exhibited very good mechanical properties—tensile strength up to 50 MPa with 425% elongation at break [for PUR based on oligo(tetramethylene carbonate) diol] and 45 MPa, 625% [for (oligo(tetramethylene succinate‐co‐carbonate)diol with 44 mol % of carbonate units]. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2014, 131, 39764.

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Poly(urethane-urea)s Based on Oligocarbonatediols Comprising Bis(carbamate)alkanes

Cited by 17 publications

References 21 publications

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Influence of the soft segment length on the properties of water‐cured poly(carbonate‐urethane‐urea)s

Segmented polyurethane elastomers derived from aliphatic polycarbonate and poly(ester‐carbonate) soft segments for biomedical applications

Propylene carbonate as a source of carbonate units in the synthesis of elastomeric poly(carbonate–urethane)s and poly(ester–carbonate–urethane)s

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