Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1995-05-18
1997-06-10
Wilson, D. R.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C07D30316, C07D30326, C07D30327
Patent
active
056376693
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention concerns monoepoxide compounds, monothiirane compounds, epoxy resins, polythiirane resins and vinyl ester resins which contain one or more discotic mesogenic moieties, as well as thermosettable compositions containing one or more of said resins and products resulting from thermosetting (curing) said curable compositions.
BACKGROUND OF THE INVENTION
A molecule composed of a disk-shaped, rigid, essentially planar core to which four or more flexible aliphatic chains or tails are attached forms the basic structure inherent to the discotic mesogen. This disk-like anisotropy of molecular shape leads to the discotic mesophase wherein the disk-like molecules organize together into thermotropic liquid crystalline columnar structures. By way of contrast, the more commonly encountered rodlike anisotropy of molecular shape, does not lead to the discotic mesophase. According to S. Chandrasekhar and G. S. Ranganath, Rep. Prog. Phys., 53(1), 57 (1989), discotic liquid crystallinity is generally classified into two structural categories: "The columnar phase, in its simplest form, has long-range translational periodicity in two dimensions and liquid-like disorder in the third, whereas the nematic phase is an orientationally ordered arrangement of discs without any long-range translational order." The discotic nematic phase contrasts to the nematic phase exhibited by numerous rodlike mesogenic molecules in that the director represents the preferred orientation of the short molecular axis versus the long molecular axis for rodlike mesogenic molecules. Some variation on the flat, planar core structure of the discotic mesogen can be tolerated while still preserving the columnar mesophase. For example, G. Cometti, E. Dalcanale and A. Du Vosel, Liquid Crystals, 11(1), 93-100 (1992) have prepared bowl-shaped molecules which exhibit a columnar liquid crystalline phase. Similarly, J. Malthete and A. Collet, Nouve. J. Chem., 9, 151 (1985) have replaced the flat, planar core structure with a conical one providing molecules which still exhibit a columnar mesophase. The presence of the flexible aliphatic chains or tails attached to the disk-shaped core is critical to achieving the discotic liquid crystalline state. Chemical structure, length and presence of branching are some of the variables relating to the aliphatic chains that are frequently manipulated to modify discotic mesophase structure and behavior. Regarding the number of flexible aliphatic chains that are required to achieve the discotic liquid crystalline state, it is fully recognized that certain exceptional molecules exist, such as the 1,7,13-trialkanoyldecacyclenes prepared and characterized by E. Keinan, S. Kumar, R. Moshenberg, R. Ghirlando and E. Wachtel, Adv. Mater., 3, 251 (1991) and the 1,3,5-tri(4-alkoxyphenoxycarbonyl)benzenes (the hexyloxy and decyloxy homologs) prepared and characterized by S. Takenaka, K. Nishimura and S. Kusabayashi, Mol. Cryst. Liq. Cryst., 111, 227-236 (1984). Thus the discotic liquid crystalline state depends upon the intermolecular attraction between the disk-like core structures leading to molecular stacking coupled with hydrophobic interaction between aliphatic chains which precludes long range three dimensional order. Thus for the 1,7,13-trialkanoyldecacyclenes the presence of the large polycyclic aromatic core maximizes attractive core to core interactions and thus appears to reduce the requirement for hydrophobic interaction between the aliphatic chains required for the discotic mesophase to be achieved. For the 1,3,5-tri(4-alkoxyphenoxycarbonyl)benzenes (the hexyloxy and decyloxy homologs), interaction of the 4-alkoxyphenoxycarbonyl groups induces molecular symmetry as determined by conformational isomerization around the ester plus increased polarizability due to the alkoxy groups and thus appears to reduce intermolecular attraction between the disk-like core structures required for the discotic mesophase to be achieved.
For molecules such as triglycidyloxynaphthalenes, specifically,
REFERENCES:
patent: 4764581 (1988-08-01), Muller et al.
patent: 4865762 (1989-09-01), Krueder et al.
patent: 4908424 (1990-03-01), Dewhirst et al.
patent: 4954583 (1990-09-01), Wang
patent: 4992488 (1991-02-01), Ruf
patent: 5037934 (1991-08-01), Yasuda et al.
patent: 5128060 (1992-07-01), Rolfe et al.
patent: 5128061 (1992-07-01), Kajiwara et al.
patent: 5128074 (1992-07-01), Nordmann et al.
patent: 5164464 (1992-11-01), Hefner, Jr. et al.
patent: 5274092 (1993-12-01), Keinan
Derwent Abstract 87-338224 (JP 62-242953, 87-10-23).
Derwent Abstract 89-359920/49 (JP 1 268 715, 26-10-89).
Derwernt Abstract 90-336094/85 (DE 3914376-A, 90-10-31.
Japanese Abstract vol. 14, No. 77 (JP 12-094791).
V. Perec, et al., Macromolecules, 25, pp. 1164-1176 (1992).
H. Lee and K. Neville, "Handbook of Epoxy Resins", McGraw-Hill, New York (1967).
Earls Jimmy D.
Hefner, Jr. Robert E.
The Dow Chemical Company
Wilson D. R.
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