Chiral compounds and compositions containing the same

Stock material or miscellaneous articles – Liquid crystal optical display having layer of specified...

Reexamination Certificate

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C252S299010, C252S299200, C560S080000, C560S256000

Reexamination Certificate

active

07052743

ABSTRACT:
The invention relates to a novel class of compounds useful as chiral dopants, which compounds are available in both enantiomeric forms. Another aspect of the invention relates to such compounds having a enantiomeric excess of one enantiomeric form, which are useful in liquid crystal formulations. Such formulations are advantageous in displays and various other products.

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patent: 5053555 (1991-10-01), Yeager et al.
patent: 0 307 951 (1989-03-01), None
patent: 9-244231 (1997-09-01), None
Birman et al., “1,1′-Spirobilindane-7,7′-diol: a novel, C2-symmetry chiral ligand”, Tetrahedron: Asymmetry, vol. 10, pp. 125-131, 1999.
CAPLUS 1969: 114866.
JP 9-244231—Abstract.
J. Am. Chem. Soc., vol. 105, No. 25, 1983, Gottarelli et al. “Induction of Cholesteric Mesophase”.
Birman, Vladimir B. et al: “1,1′-Spirobiindan-7,7′-diol: a novel, C2-symmetric chiral ligand” Tetrahedron: Asymmetry, 10(1), 125-131 CODEN: TASYE3; ISSN: 0957-4166, 1999, XP002315481 P. 126, Scheme 1, e.g. compounds 14 to 16; p. 127, compounds 16 to 19; Scheme 2; p. 130, item 3.9.
Database Beilstein, Institut Zur Forderung Der Chemischen, Wissenschaften, Frankfurt am Main, DE; XP002315483, Database accession No. BRN 2034658, abstract & Blatchly et al.: “Thiele-Winter Acetoxylation of Quinones. Part IV. Quinones containing One or More t-Butyl Groups” J. Chem. Soc. Perkin Trans. 1, 1972, pp. 2286-2291, XP009043084.
Database CA Online, Chemical Abstracts Service, Columbus, Ohio, US; Tan, Shiro et al: “Novel diazonaphthoquinone photoactive compound for g-line/i-line compatible positive photoresist,” XP002315484, retrieved from STN, Database assession No. 1990:601153, abstract, and Proceedings of SPIE—The International Society for Optical Engineering, 1262 (Adv. Resist Technol. Process. 7), 513-26 CODEN: PSISDG; ISSN: 0277-786X, 1990.
Database CA Online, Chemical Abstracts Service, Columbus, Ohio, US; Sanchez-Viesca, F. et al: “Preparation and spectroscopy study of 4,4′, 6,6′, 7,7′-hexamethoxy-3, 3, 3′, 3′-tetramethyl-1, 1′-spiro-bis-hydrinden” XPOO2315484, retrieved from STN, Database accession No. 1981: 461829, abstract, and Revista Latinoamericana de Quimica, 12(1), 27-9 CODEN: RLAQA8: ISSN; 0370-5943, 1981.
Dtabase CA Online, Chemical Abstracts Service, Columbus, Ohio, US; Uenishi, Kazuya et al: “Structural effects of diazonaphthoquinonephotoactive compound backbone on resist lithographic properties,” XP002315486, retrieved from STN, Database accession No. 1991:690953, abstract, and Proceedings of SPIE—The International Society for Optical Engineering, 1566 (Adv. Resist Technol. Process. 8), 102-16 CODEN: PSISDG; ISSN: 0277-786X, 1991.
Zhou, Hai et al: “Highly Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc to Enones using Chiral Spiro Phosphoramidites as Ligands,” Journal of Organic Chemistry, 68(4), 1582-1584 CODEN: JOCEAH; ISSN: 0022-3263, vol. 68, No. 4, 2003, pp. 1582-1584, XP002315482, p. 1582, Figure 1; sCHEME 1; Abstract.

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