Alternating poly(ester amide)s from succinic anhydride and α,ω‐amino alcohols: synthesis and thermal characterization

Fey, Thomas; Hölscher, Markus; Keul, Helmut; Höcker, Hartwig

doi:10.1002/pi.1354

Cited by 20 publications

(21 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The series of PDEU(x) with even numbers of methylene chains of urethanediol units (x = 2, 4, 6) showed a slightly higher T m value than the PDEU(x) series with odd numbers of methylene chains (x = 3, 5). Fey et al reported similar behavior for poly(ester-amide)s [22,23] and polyurethanes. [24,25] The decomposition temperatures at 5 wt % weight loss (T d(5 %) ) of the PDEUs showed similar values around 313-318 8C except for PDEU(2), whose slightly lower T d(5 %) value may be attributed to the low thermal stability of urethanediol(2) itself.…”

Section: Thermal and Mechanical Properties Of The Polyurethanessupporting

confidence: 57%

Chemoenzymatic Synthesis and Chemical Recycling of Sustainable Polyurethanes

et al. 2008

View full text Add to dashboard Cite

Two novel types of chemically recyclable ester-containing polyurethanes, namely, a diol-diacid-type poly(diester-urethane) (PDEU) and a hydroxy acid type poly(ester-urethane) (PEU), were prepared by a green synthetic route that avoids the use of hazardous diisocyanate. The urethane linkage was introduced by the reaction of ethylene carbonate with amino alcohols and amino acids to form urethanediol and urethane-containing hydroxy acids, respectively. The urethanediol underwent polymerization with dimethyl adipate in the presence of lipase to produce a high-molecular-weight PDEU, while PEU was prepared by the lipase-catalyzed direct polycondensation of the urethane-containing hydroxy acid monomer. The periodic introduction of ester linkages into the polyurethane chain afforded primary biodegradation points and chemically recyclable segments. Both PDEU and PEU were readily degraded in the presence of lipase into oligomers which were readily repolymerized in the presence of the same enzyme.

show abstract

Section: Thermal and Mechanical Properties Of The Polyurethanessupporting

confidence: 57%

Chemoenzymatic Synthesis and Chemical Recycling of Sustainable Polyurethanes

et al. 2008

View full text Add to dashboard Cite

show abstract

“…In a previous paper [11] we have shown that poly(ester amide)s from succinic anhydride and amino alcohols, upon thermal degradation, result in N-hydroxyalkyl imides 6a-e and not in the corresponding cyclic ester amides 7a-e (Scheme 2). Theoretical calculations have shown that cyclic ester amides based on succinic anhydride are clearly richer in energy than are the corresponding N-hydroxyalkyl imides.…”

Section: Cyclic Ester Amides 4a-ementioning

confidence: 99%

Interconversion of Alternating Poly(ester amide)s and Cyclic Ester Amides from Adipic Anhydride and α,ω‐Amino Alcohols

Fey

Keul

Höcker

2003

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

Poly(esters amide)s from adipic anhydride and α,ω‐amino alcohols were obtained by polycondensation of α‐carboxyl‐ω‐hydroxyl amides under mild conditions in solution or by bulk polycondensation at elevated temperatures. For the polycondensation in bulk the influence of catalyst and of temperature on the number‐average molecular weight was studied. At a temperature of 170 °C the polycondensation process is followed by a ring‐closing depolymerisation and the formation of cyclic ester amides. Ten‐ to fourteen‐membered cyclic ester amides were obtained and characterized. The ring‐opening polymerisation of these cyclic ester amides leads, in a controlled mode, to poly(ester amide)s. The interconversion of poly(ester amide)s and cyclic ester amides by ring‐closing depolymerisation and ring‐opening polymerisation is possible. The poly(ester amide)s from adipic anhydride and homologous α,ω‐amino alcohols H2N(CH2)xOH (x = 2–6) are semicrystalline materials, their melting points show the odd/even effect observed for [n]‐polyamides and [n]‐polyurethanes.

show abstract

“…The properties of these polymers are not only determined by the building blocks but also by the concentration and by the distribution -random or regular -of the functional groups. Excellent examples of this principle are the poly-(ester amide)s [6][7][8][9][10][11][12][13][14][15][16][17]. Due to hydrogen bonds between the amide groups, these materials have improved mechanical and thermal properties compared with polyesters; the ester groups are mainly responsible for hydrolytical degradation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of alternating poly(amide urea)s and poly(amide urethane urethane)s from ε-caprolactam, diamines, and diphenyl carbonate or ethylene carbonate

Ubaghs¹,

Sharma²,

Keul³

et al. 2003

E-Polymers

Self Cite

View full text Add to dashboard Cite

Alternating poly(amide urea)s from ε-caprolactam, diamines H 2 N-(CH 2 ) x -NH 2 (x = 2 -4), and diphenyl carbonate were prepared in two steps. The microstructure of the poly(amide urea)s, as determined by means of 1 H NMR spectroscopy, reveals a strictly alternating sequence of the building blocks. The molecular weights and polydispersities obtained were 7500 < M n < 10 000 and 1.48 < M w /M n < 1.56, respectively. Thermal properties were determined by means of differential scanning calorimetry (DSC) (163.9°C < T m < 197.2°C; 55.5°C < T g (2 nd heating) < 72.2°C), and thermogravimetric analysis (TGA). TGA shows a three-step decomposition at 200, 350, and 450°C, which was attributed to the cleavage of O-phenyl urethane end groups, as well as urea and amide linkages. These assignments were made by comparison with model compounds. Furthermore, alternating poly-(amide urethane urethane)s from ε-caprolactam, diamines, and ethylene carbonate were prepared in three steps. The microstructure of the poly(amide urethane urethane)s, as determined by means of 1 H NMR spectroscopy, reveals imperfections. The molecular weights and polydispersities obtained were 5400 < M n < 17 000 and 2.08 < M w /M n < 2.99, respectively. Thermal properties were determined by means of DSC (155.9°C < T m < 159.0°C; 35.5°C < T g (2 nd heating) < 39.0°C) and TGA. TGA shows a complex decomposition due to the formation of ethylene carbonate by cleavage of the urethane groups (at approx. 230°C) and formation of poly(amide urea)s. The newly formed poly(amide urea)s decompose in a similar way as the poly(amide urea)s.

show abstract

Alternating poly(ester amide)s from succinic anhydride and α,ω‐amino alcohols: synthesis and thermal characterization

Cited by 20 publications

References 30 publications

Chemoenzymatic Synthesis and Chemical Recycling of Sustainable Polyurethanes

Chemoenzymatic Synthesis and Chemical Recycling of Sustainable Polyurethanes

Interconversion of Alternating Poly(ester amide)s and Cyclic Ester Amides from Adipic Anhydride and α,ω‐Amino Alcohols

Synthesis and characterization of alternating poly(amide urea)s and poly(amide urethane urethane)s from ε-caprolactam, diamines, and diphenyl carbonate or ethylene carbonate

Contact Info

Product

Resources

About