Synthesis of Novel Polyurethanes and Polyureas by Polyaddition Reactions of Dianhydrohexitol Configurated Diisocyanates

Bachmann, Frank; Reimer, J.M.; Ruppenstein, Marcus; Thiem, Joachim

doi:10.1002/1521-3935(20011101)202:17<3410::aid-macp3410>3.0.co;2-q

Cited by 73 publications

(55 citation statements)

References 6 publications

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“…XXXX, XXX, XXX−XXX by reaction with phosgene. 194 Likewise, the dithiodiisocyanate derivative was prepared from the 2,5-diamino-2,5-dideoxy-Lidide (84) and thiophosgene. Thus, poly(thio)urethanes and poly(thio)ureas were synthesized from the three monomers (82−84).…”

Section: Polyurethanesmentioning

confidence: 99%

“…Koning et al described some poly-(urethane urea) dispersions containing renewable building blocks including isosorbide (1) 181 and thermoplastic poly(ester urethane urea)s from biobased monomers, such as L-lysine diisocyanate, isoidide diisocyanate, 1,4-diaminobutane, and diaminoisoidide (84). 219 Thiem et al 194 described the preparation of fully sugar-based polyureas by polyaddition reactions of the 1,6-diamino-1,6-dideoxy-dianhydrohexytols (82−84) to the isoidide diisocyanate. Galbis and co-workers 107 also described the synthesis of a semicrystalline polyurea (Scheme 51) by polyaddition reaction of the O-benzyl-1,6-diamino-L-arabinitol (66) to HDI.…”

Section: Polyureasmentioning

confidence: 99%

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Synthetic Polymers from Sugar-Based Monomers

et al. 2015

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Scheme 2. (a) Lactide Polymerization Coinitiated by Carbohydrates; (b) Copolymerization of Lactone Derived from D-Gluconolactone and ε-Caprolactone (CL) Scheme 3. Polyesters Based on Pentitols and Pentaric Acid Scheme 4. Protein-Resistant Polyesters Based on Galactitol and D-Mannitol Scheme 5. Polyesters Based on L-Tartaric Acid Derivatives Scheme 6. PBS Copolyesters Based on L-Tartaric Acid Derivatives Scheme 7. Erythritol-Based Polyesters Containing Triazol Rings

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Section: Polyurethanesmentioning

confidence: 99%

Section: Polyureasmentioning

confidence: 99%

Synthetic Polymers from Sugar-Based Monomers

et al. 2015

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“…In particular, the former two compounds are readily available from D ‐glucose and D ‐mannose, respectively, by hydrogenation followed by acid‐catalyzed intramolecular dehydration 15. These carbohydrate‐based stereoisomeric diols 1a – 1c represent highly useful diol components for the synthesis of a variety of polymers such as polyesters,16–27 polyethers,28 polyurethanes,29–31 polyureas,31 poly(ester anhydride)s,32 poly(ester amide)s,33–35 poly(ester carbonate)s,36 and polycarbonates 37, 38. We have so far reported the synthesis of various biodegradable polymers based on 1a – 1c .…”

Section: Introductionmentioning

confidence: 99%

Biodegradable polymers based on renewable resources. IX. Synthesis and degradation behavior of polycarbonates based on 1,4:3,6‐dianhydrohexitols and tartaric acid derivatives with pendant functional groups

Yokoe

Aoi

Okada

2005

J. Polym. Sci. A Polym. Chem.

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Novel polycarbonates, with pendant functional groups, based on 1,4:3,6‐dianhydrohexitols and L‐tartaric acid derivatives were synthesized. Solution polycondensations of 1,4:3,6‐dianhydro‐bis‐O‐(p‐nitrophenoxycarbonyl)hexitols and 2,3‐di‐O‐methyl‐L‐threitol or 2,3‐O‐isopropylidene‐L‐threitol afforded polycarbonates having pendant methoxy or isopropylidene groups, respectively, with number average molecular weight (Mn) values up to 3.61 × 104. Subsequent acid‐catalyzed deprotection of isopropylidene groups gave well‐defined polycarbonates having pendant hydroxyl groups regularly distributed along the polymer chain. Differential scanning calorimetry (DSC) demonstrated that all the polycarbonates were amorphous with glass transition temperatures ranging from 57 to 98 °C. Degradability of the polycarbonates was assessed by hydrolysis test in phosphate buffer solution at 37 °C and by biochemical oxygen demand (BOD) measurements in an activated sludge at 25 °C. In both tests, the polycarbonates with pendant hydroxyl groups were degraded much faster than the polycarbonates with pendant methoxy and isopropylidene groups. It is noteworthy that degradation of the polycarbonates with pendant hydroxyl groups was remarkably fast. They were completely degraded within only 150 min in a phosphate buffer solution and their BOD‐biodegradability reached nearly 70% in an activated sludge after 28 days. The degradation behavior of the polycarbonates is discussed in terms of their chemical and physical properties. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 3909–3919, 2005

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“…16,17 Isosorbide is thermally stable, available in large quantities and useful for the synthesis of bio-based polymers, such as polyesters, [18][19][20][21][22][23][24][25][26][27][28] polyamides 29 and polyurethanes. [30][31][32][33][34][35][36] A polycarbonate derived from petroleum is a bisphenol A-based polycarbonate (BPAPC). BPAPC possesses superior properties, such as high transparency, impact resistance, high tensile strength, durability and heat resistance.…”

Section: Introductionmentioning

confidence: 99%

Preparation and mechanical properties of a copolycarbonate composed of bio-based isosorbide and bisphenol A

Lee

Takagi

Okamoto

et al. 2015

Polym J

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A series of copolycarbonates were prepared by transesterification polymerization of isosorbide, bisphenol A and diphenylcarbonate using several catalysts. The copolymers with the highest molecular weights were obtained using N,N-dimethylaminopyridine as a catalyst. The storage moduli of the polymers ranged from 2.3 to 3.5 GPa at 25°C, and the tensile moduli were 1.7-2.6 GPa, increasing with the isosorbide content. The storage and tensile moduli of the polymers indicated that they could exhibit better strength than bisphenol A-based polycarbonates. These properties endow the polymers with potential for use as high-performance materials.

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Synthesis of Novel Polyurethanes and Polyureas by Polyaddition Reactions of Dianhydrohexitol Configurated Diisocyanates

Cited by 73 publications

References 6 publications

Synthetic Polymers from Sugar-Based Monomers

Synthetic Polymers from Sugar-Based Monomers

Biodegradable polymers based on renewable resources. IX. Synthesis and degradation behavior of polycarbonates based on 1,4:3,6‐dianhydrohexitols and tartaric acid derivatives with pendant functional groups

Preparation and mechanical properties of a copolycarbonate composed of bio-based isosorbide and bisphenol A

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