Polymers of Carbonic Acid. 22. Cholesteric Polycarbonates Derived from (<i>S</i>)-((2-Methylbutyl)thio)hydroquinone or Isosorbide

Kricheldorf, Hans R.; Sun, Shih‐Jieh; Gerken, Andreas; Chang, Teh‐Chou

doi:10.1021/ma960494d

Cited by 53 publications

(34 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the optical properties were largely different. In the case of 1a and 1b a "sausage texture" was found which we have never observed for any other class of cholesteric polyesters (including polycarbonates and polyesterimides) [10][11][12][13][14][15][16][17][18][19] . On the other hand, the polyesters of structure 1a, b did never form a Grandjean (GJ) texture 20) .…”

Section: Introductioncontrasting

confidence: 45%

Layer structures, 13. Chiral sanidic polyesters derived from 2,5-bis(alkylthio)terephthalic acids

Kricheldorf¹,

Wulff

Wutz

1999

Macromol. Chem. Phys.

Self Cite

View full text Add to dashboard Cite

SUMMARY: Two chiral terephthalic acids were synthesized from (S)-2-methylbutane-1-thiol and bromoterephthalic acid or 2,5-dibromoterephthalic acid. A series of chiral polyesters was then prepared by polycondensation of silylated 4,49-dihydroxybiphenyl and mixtures of 2,5-bis(dodecylthio)terephthaloyl chloride and 2,5-bis((S)-2-methylbutylthio)terephthaloyl chloride. The copolyesters were characterized by elemental analyses, viscosity, DSC and X-ray measurements, and optical microscopy. Depending on the reaction conditions low and high molecular weights were obtained. In addition to a solid sanidic phase these polyesters form a chiral sanidic LC-phase and a chiral nematic LC-phase. However, in contrast to a normal cholesteric melt, these polyesters did not form a Grandjean texture but display the unusual "sausage texture".

show abstract

Section: Introductioncontrasting

confidence: 45%

Layer structures, 13. Chiral sanidic polyesters derived from 2,5-bis(alkylthio)terephthalic acids

Kricheldorf¹,

Wulff

Wutz

1999

Macromol. Chem. Phys.

Self Cite

View full text Add to dashboard Cite

show abstract

“…This solid was collected on a glass filter and washed with a 5 wt % aqueous solution of NaHCO 3 and several times with water. The crude product was recrystallized from ethyl acetate and dried in vacuo at 40°C 24, 26. Yield: 26.15 g (65.7%), purity: 98+ %, mp: 107°C–109°C.…”

Section: Methodsmentioning

confidence: 99%

“…Radiation‐curable powder coating resins were prepared by ring‐opening polymerization of 2,2‐dimethyl‐1,3‐trimethylene carbonate, followed by end‐capping with methacrylate moieties 18. Different (co)polycarbonates based on the DAHs were also described in literature, but so far their functionalities and subsequent coating application were not elaborated upon 19–30…”

Section: Introductionmentioning

confidence: 99%

Chemistry, functionality, and coating performance of biobased copolycarbonates from 1,4:3,6‐dianhydrohexitols

Noordover

Haveman

Duchateau

et al. 2011

J of Applied Polymer Sci

View full text Add to dashboard Cite

Biobased polycarbonates were synthesized from 1,4:3,6-dianhydro-D-glucitol, 1,4:3,6-dianhydro-L-iditol, and 1,4:3,6-dianhydro-D-mannitol as the principal diols, using different types of carbonyl sources. The (co)polycarbonates resulting from polycondensation reactions in solution using triphosgene consisted of several types of polymer chains with respect to chain topology (e.g., linear or cyclic chains) and end-group structure (e.g., hydroxyl, chloroformate or alkyl chloride end-groups). The introduction of flexible comonomers seemed to increase the amount of cyclic structures in the product mixtures. The melt polymerization of diphenyl carbonate with 1,4:3,6-dianhydrohexitols required high reaction temperatures and led to almost exclusively hydroxy-functional poly(1,4:3,6-dianhydrohexitol carbonate)s. Copolymerizing the 1,4:3,6-dianhydrohexitols with 1,3-propanediol and diphenyl carbonate at high temperature resulted in the partial loss of 1,3-propanediol. On the other hand, by melt polycondensation of 1,4:3,6-dianhydrohexitol-based bis(phenyl carbonate) monomers in combination with primary diols and/or triols, the insertion of the primary alcohols could be achieved in a more controlled way. OH-functional materials were prepared, having suitable molecular weights, T g values, thermal stability, and melt viscosity profiles for (powder) coating applications. These functional biobased (co)polycarbonates were cured with polyisocyanate curing agents, resulting in colorless to pale yellow transparent, glossy coatings with good mechanical performance and solvent resistance.

show abstract

“…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.

View full text Add to dashboard Cite

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

show abstract

Polymers of Carbonic Acid. 22. Cholesteric Polycarbonates Derived from (S)-((2-Methylbutyl)thio)hydroquinone or Isosorbide

Cited by 53 publications

References 11 publications

Layer structures, 13. Chiral sanidic polyesters derived from 2,5-bis(alkylthio)terephthalic acids

Layer structures, 13. Chiral sanidic polyesters derived from 2,5-bis(alkylthio)terephthalic acids

Chemistry, functionality, and coating performance of biobased copolycarbonates from 1,4:3,6‐dianhydrohexitols

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

Contact Info

Product

Resources

About