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US 6,616,989 B1Granted
Isoxazole derivatives, and their use in liquid-crystalline mixtures
AssigneeClariant International Ltd.
InventorsWolfgang Schmidt, Barbara Hornung, Rainer Wingen
Life of this patent
Estimating the term…
Abstract
Isoxazole derivatives of the formula (I) where the symbols and indices have the following meanings, for example: T is X is S or O R1 and R2 are identical or different and are each hydrogen, F, CN or a straight-chain or branched C1-C20-alkyl or C2-C20-alkenyl radical (with or without asymmetric carbon atoms), A1 and A2 are undirected and identical or different and are each phenylene-1,4-diyl, M1 is undirected and is —OC(═O)—, —OCH2—, —SC(═O)—, —SCH2—, —CH2CH2—, —OC(═O)CH2CH2—, —OCH2CH2CH2—, —C≡C—, —(CH2)4— or a single bond; a is 0 or 1, are used in liquid-crystal mixtures.
Claims12
An isoxazole derivative of the formula (I)
- where the symbols and indices have the following meanings:
- T is
- R1 and R2 are identical or different and are each hydrogen, F, CN or a straight-chain or branched C1-C20-alkyl or C2-C20-alkenyl radical (with or without asymmetric carbon atoms), where
- a) one to three nonterminal CH2 groups may be replaced, independently of one another, by —O—, or —C(═O)—, with the proviso that heteroatoms cannot be linked directly to one another;
- and/or
- b) one CH2 group may be replaced by —CH═CH— or —C≡C—;
- and/or
- c) one CH2 group may be replaced by —Si(CH3)2—, cyclopropane-1,2-diyl, oxirane-2,3-diyl cyclobutane-1,3-diyl, cyclopentane-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl or cyclohexane-1,4-diyl;
- and/or
- d) one or more H atoms may be replaced, independently of one another, by F or CN;
- e) in the case of an alkyl or alkenyl radical containing asymmetric carbon atoms, the asymmetric carbon atoms have —CH3, —OCH3, —CF3, —F, —CN and/or —Cl as substituents;
- f) with the proviso that-only one of R1 and R2 is a hydrogen, F or CN;
- A1 and A2 are undirected and identical or different and are each phenylene-1,4-diyl, unsubstituted or monosubstituted or disubstituted by CN or F, phenylene-1,3-diyl, unsubstituted or monosubstituted or disubstituted by CN or F, cyclohexane-1,4-diyl, in which one or two H atoms may be replaced, independently of one another by CN, CH3 or F, 1-cyclohexene-1,4-diyl, in which one H atom may be replaced by F, pyridine-2,5-diyl, unsubstituted or monosubstituted by F, thiophene-2,5-diyl, unsubstituted or monosubstituted by F, furan-2,5-diyl or naphthalene-2,6-diyl, unsubstituted or monosubstituted or disubstituted by CN or F;
- M1 is undirected and is —OC(═O)—, —OCH2—, —SC(═O)— —SCH2— —CH2CH2—, —OC(═O)CH2CH2— —OCH2CH2CH2—, —C≡C—, —(CH2)4— or a single bond;
- a is 0 or 1.
12 more elements
An isoxazole derivative of the formula (I)
- where the symbols and indices have the following meanings:
- T is
- X is S
- R1 and R2 are identical or different and are each hydrogen, F, CN or a straight-chain or branched C1-C20-alkyl or C2-C20-alkenyl radical (with or without asymmetric carbon atoms), where
- (a) one to three nonterminal CH2 groups may be replaced, independently of one another, by —S— or —C(═O)—, with the proviso that heteroatoms cannot be linked directly to one another;
- or
- (b) one CH2 group may be replaced by —CH═CH— or —C≡C—;
- and/or
- (c) one CH2 group may be replaced by —Si(CH3)2—, cyclopropane-1,2-diyl, oxirane-2,3-diyl cyclobutane-1,3-diyl, cyclopentane-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl or cyclohexane-1,4-diyl;
- and/or
- (d) one or more H atoms may be replaced, independently of one another, by F or CN;
- (e) in the case of an alkyl or alkenyl radical containing asymmetric carbon atoms, the asymmetric carbon atoms have —CH3, —OCH3, —CF3, —F, —CN and/or —Cl as substituents;
- (f) with the proviso that only one of R1 and R2— is a hydrogen, F or CN;
- A1 and A2 are undirected and identical or different and are each phenylene-1,4-diyl, unsubstituted or monosubstituted or disubstituted by CN or F, phenylene-1,3-diyl, unsubstituted or monosubstituted or disubstituted by CN or F, cyclohexane-1,4-diyl, in which one or two H atoms may be replaced, independently of one another, by CN, CH3 or F;
- 1-cyclohexene-1,4-diyl, in which one H atom may be replaced by F, pyridine-2,5-diyl, unsubstituted or monosubstituted by F, thiophene-2,5-diyl, unsubstituted or monosubstituted by F;
- furan-2,5-diyl or naphthalene-2,6-diyl, unsubstituted or monosubstituted or disubstituted by CN or F;
- M1 is undirected and is —OC(═O)—, OCH2—, —SC(═O)—, —SCH2—, —CH2CH2—, —OC(═O)CH2CH2—, —OCH2CH2CH2—, —C≡C—, —(CH2)4— or a single bond;
- and
- a is 0 or 1.
16 more elements
Dependencies are inferred from the claim text.