NDLI: Polyurethanes with pendant hydroxy groups: polycondensation of D-mannitol-1,2:5,6-dicarbonate with diamines

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Polyurethanes with pendant hydroxy groups: polycondensation of D-mannitol-1,2:5,6-dicarbonate with diamines

Content Provider	Taylor & Francis Online
Author	Keul, Helmut Prömpers, Günter Höcker, Hartwig
Abstract	The bis(ethylene carbonate) monomers 3,4-O-isopropylidene-D-mannitol-1,2:5,6-dicarbonate (2) and D-mannitol-1,2:5,6-dicarbonate (1) were prepared fromD-mannitol in yields of 81 and 74%, respectively. These AA-type monomers were reacted with α, ω-diamines (H2N—(CH2) x –NH2; x = 2–10 and 12) as BB-type monomers in the sense of a polycondensation reaction. The molecular weights of the polyurethanes with pendant hydroxy groups obtained were determined by means of gel permeation chromatography in dimethylacetamide/LiCl and are in the range of 20 × 103 to 87 × 103 with polydispersity indices of ca. 1.6. The polyurethanes show primary and secondary hydroxy groups with a ratio of ca. 15:85. This is a consequence of the different direction of opening of the substituted ethylene carbonate ring which results in structurally isomeric repeating units. The polyurethanes obtained from 2 and diamines with two free hydroxy groups and two protected hydroxy groups in the repeating unit are semicrystalline materials with melting points between 160 and 190°C and glass transition temperatures of 64 to 79°C. The polyurethanes derived from 1 and diamines with four free hydroxy groups in the repeating unit show glass transition temperatures of 50 to 70°C; no melting transition is observed before decomposition starts at ca. 200°C. Polymer analogous esterification reactions were successfully performed with acyl chlorides; the properties of the acylated polyurethanes differ from those of the starting polymers and depend on the acyl chloride used.
Starting Page	547
Ending Page	569
Page Count	23
File Format	PDF HTM / HTML
ISSN	15685551
DOI	10.1163/156855505774597830
Journal	Designed Monomers and Polymers
Volume Number	8
Issue Number	6
Language	English
Publisher	Taylor & Francis Group
Publisher Date	2012-04-02
Access Restriction	Open
Subject Keyword	D-MANNITOL-12:5,6-DICARBONATE POLYURETHANES PENDANT HYDROXY GROUPS POLYCONDENSATION BIS(ETHYLENE CARBONATE)S DIAMINES POLYMER ANALOGOUS REACTIONS MICROSTRUCTURE NMR THERMAL PROPERTIES
Content Type	Text
Resource Type	Article
Subject	Chemistry Materials Chemistry Chemical Engineering Polymers and Plastics

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