Polymerizable, chiral compounds and their use

• US 5,886,242 A
• Filed: 01/12/1998
• Issued: 03/23/1999
• Est. Priority Date: 12/11/1993
• Status: Expired due to Term

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Delavier, Paul, Laupichler, Lothar, Wagenblast, Gerhard, Siemensmeyer, Karl, Etzbach, Karl-Heinz, Vill, Volkmar
• Primary Examiner(s): Richter, Johann
• Assistant Examiner(s): Oswecki, Jane C.
• Application Number:
  US09/006,003
• Time in Patent Office: 435 Days
• Field of Search: 544/224, 544/242, 546/249, 548/136, 548/143, 549/29, 585/25, 585/26, 585/27, 252/299.01, 252/299.61, 252/299.62, 252/299.66
• US Class Current: 585/25
• CPC Class Codes: C07C 69/92 with etherified hydroxyl groups
• CPC Class Codes: C07C 69/94 of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C08F 20/30 containing aromatic rings in the alcohol moiety
• CPC Class Codes: C09K 19/0422 Sugars polysaccharides C09K19/3819
• CPC Class Codes: C09K 19/2028 containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
• CPC Class Codes: C09K 19/30 containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
• CPC Class Codes: C09K 19/3068 chain containing -COO- or -OCO- groups
• CPC Class Codes: C09K 19/322 Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
• CPC Class Codes: C09K 19/3463 Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• CPC Class Codes: C09K 19/3491 having sulfur as hetero atom
• CPC Class Codes: C09K 2019/0448 the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
• CPC Class Codes: C09K 2019/323 containing a binaphthyl
• CPC Class Codes: C09K 2019/3408 Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
• CPC Class Codes: C09K 2019/3425 Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems
• CPC Class Codes: C09K 2019/3427 Six-membered ring with 3 or more oxygen atoms

Abstract

The invention relates to chiral compounds containing at least one divalent or polyvalent chiral group, at least one polymerizable group, at least one spacer and at least one mesogenic group, and to their use as polymerizable, chiral dopes for the preparation of cholesteric networks.

The novel compounds are suitable for use in electro-optical displays or as chiral dopes for nematic or cholesteric liquid crystals in order to produce layers which reflect in colors.

Claims

1. A compound of the formula

View Dependent Claims (2, 3, 4, 5, 6, 7)

2. A compound as claimed in claim 1, where r is 0 or 1.

3. A compound as claimed in claim 1, where n=2.

4. A compound as claimed in claim 1, where X is ##STR61## where L is C₁ - to C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, COOR, OCOR, CONHR or NHCOR, and R is as defined above.

5. A compound as claimed in claim 2, where X is ##STR62## where L is C₁ - to C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, COOR, OCOR, CONHR or NHCOR, and R is defined above.

6. In a process for the preparation of a cholesteric, network the improvement comprising incorporating the compound of claim 1 therein as a polymerizable, chiral dope.

7. The polymerizable, chiral compound as claimed in claim 1,

wherein A is a chain of 2-30 carbon atoms, optionally interrupted in the chain with O, S, NH or NCH₃, and optionally substituted on the chain with fluorine, chlorine, bromine, cyano, methyl or ethyl;

wherein T is selected from the group consisting of the following structures;

##STR63## which structure may be unsubstituted or substituted by fluorine, chlorine, bromine, cyano, hydroxyl or nitro;

and wherein Z is selected from the group consisting of the following structures;

##STR64## where R is defined above.