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Abstract

4-Propargyloxy benzoic acid, 6-propargyloxy-2-naphthoic acid and 4′-propargyloxybiphenyl-4-carboxylic acid were synthesized from the corresponding hydroxy acids and converted into the acid chlorides. Diesters were then prepared by the reaction of these acid chlorides with diphenols such as hydroquinone, methylhydroquinone n-octylthiohydroquinone and phenylhydroquinone. Most of these diesters form an enantiotropic nematic melt but some diesters form a monotropic liquid crystal phase. Cholesteric phases were observed for diesters of (S)-2-methylbutylthiohydroquinone. Diesters derived from 6-propargyloxy-2-naphthoic acid begin to crosslink above 200 °C with an optimum cure temperature of 240–250 °C. The crosslinking of the 4′-propargyloxybiphenyl-4-carboxylic acid derivatives occurs at a temperature 60 °C higher. Several diesters crosslink in the nematic state, but most of them undergo isotropization before completion of the crosslinking process. Numerous cholesteric blends of nematic diesters and chiral diesters of isosorbide were studied and Grandjean textures with bright colours were found. Thermal crosslinking in the cholesteric phase was feasible in several cases.

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References

[1] Hegenrother P M 1980 J. Macromal. Sci.-Rev. Macromol. Chem. C 19 1-1

[2] Lee B H and Marvel C S 1982 J. Polym. Sci., Polym. Chem. Ed. 20 393-393

[3] Ishiza K , Prabhu V D G , Draney D , Lee B H and Marvel C S 1982 J. Polym. Sci., Polym. Chem. Ed. 20 2851-2851

[4] Strohmer F , Ahne H , Birkle S , Hammerschmidt A and Geibel K 1994 Ger. Offen. DE 4.226.994 to Siemens AG; 1994 Chem. Abst. 120 219478s-219478s

[5] Mallon J J and Adams P M 1993 J. Polym. Sci, Part A, Polym. Chem. 31 2249-2249

[6] Jahromi S and Mijs W J 1994 Mol. Cryst. Liq. Cryst. Sci., Technol. Sect. A 250 209-209

[7] Carfagna C , Amendola E and Giamberini M 1994 Macromol. Chem. Phys. 195 279-279, 2307-2307

[8] Giamberini M , Amendola E and Carfagna C 1995 Macromol. Chem. Phys. 16 97-97

[9] Barclay G G , Ober C K , Papathomas K J and Wang D W 1992 Macromolecules 25 2947-2947

10.

[10] Hoyt A E and Huang S M 1995 J.M.S.-Pure Appl. Chem. A 32 1931-1931

11.

[11] Kitamura T , Lee C H , Taniguchi H , Matsumoto M and Sano Y 1994 J. Org. Chem. 59 8053-8053

12.

[12] Douglas E P , Langlois D A and Beniccwicz B C 1994 Chem. Mater. 6 1925-1925

13.

[13] Stumpe J , Ziegler A , Berghahn M and Kricheldorf H R 1995 Macromolecules 28 5306-5306

14.

[14] Kricheldorf H R , Probst N , Gurau M and Berghahn M 1995 Macromolecules 28 6565-6565

15.

[15] Kricheldorf H R and Probst N 1995 Macromol. Chem. Phys. 196 3511-3511

16.

[16] Kricheldorf H R and Probst N 1995 High Perform. Polym. 7 471-471

17.

[17] Bouliigand Y 1973 J. Phys. 34 603-603

18.

[18] de Jeu H W and Vertogen G 1977 Thermotropic Liquid Crystals Fundamentals (Berlin: Springer)

19.

[19] Kricheldorf H R , Sun S-J , Gerken A and Chang T Ch 1996 Macromolecules 29 8077-8077

20.

[20] Reppe W 1955 Liebigs Ann. Chem. 596 76-76

21.

[21] Vill V , Fischer F and Thiem J 1988 Z. Naturforsch. 443a 1119-1119

22.

[22] Kricheldorf H R and Probst N 1995 Macromol. Rapid Commun. 16 231-231

23.

[23] Kricheldorf H R and Probst N 1995 High Perform. Polym. 7 461-461

New Polymer Syntheses 87. Thermosetting Nematic or Cholesteric Diesters Having Propargyl Endgroups

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