US 6,395,351 B1Granted

Polymerisable liquid crystalline compounds

AssigneeRolic AG

InventorsCarsten Benecke, Teodor Lukàc, Angela Ohlemacker

Life of this patent

Estimating the term…

Loading patent…

Abstract

Compounds with the general formula (I): R—S1—A—Z1—B—S2—R, where A and B are independent ring systems with the formulae (a1), (a2) or (b), whereby in the trans-1,4-cyclohexylene ring, one or two non-adjacent CH2 groups may be replaced by oxygen, and whereby, in the 1,4-phenylene ring, one or two non-adjacent CH groups may be replaced by nitrogen; L1, L2, L3 represent, independently, hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkyloxy, C1-C20-alkyloxy carbonyl, formyl, C1C20-alkyl carbonyl, C1-C20-alkyl carbonyloxy, halogen, cyano or nitro; Z1, Z2, Z3 represent, independently, a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, —(CH2)4—, —O(CH2)3—, —(CH2)3O— or —C≡C—; S1, S2 represent a spacer unit; R represents crosslinkable groups, with the proviso that at least one of the ring systems A or B represents a ring system with the formula (a1) or (a2), Z1 or Z2 denoting a single bond.

Claims20

Dependent claims

A compound of the formula I:

R—S1—A—Z1—B—S2—R I
where
A and B are each an independent ring system and each have the formulae a1, a2 or b,
whereby, in the trans-1,4-cyclohexylene ring, one or two non-adjacent CH2 groups may be replaced by oxygen, and whereby, in the 1,4-phenylene ring, one or two non-adjacent CH groups may be replaced by nitrogen;
L1, L2, L3 represent, independently, hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkyloxy, C1-C20-alkyloxy carbonyl, formyl, C1-C20-alkyl carbonyl, C1-C20-alkyl carbonyloxy, halogen, cyano or nitro;
Z1, Z2, Z3 represent, independently, a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, —(CH2)4—, —O(CH2)3—, —(CH2)3O— or —C≡C—;
S1, S2 each independently represent a straight chain or branched alkylene grouping —(CH2)r, unsubstituted or substituted singly or multiply with fluorine, or —((CH2)2—O)r—, or a chain with the formula —(CH2)r—Y—(CH2)s—, where Y represents a single bond or the linking functional group —O—, —COO—, —OOC—, —NR1—, NR1—CO—, —CO—NR1—, NR1—COO—, —OCO—NR1—, NR1, —CO—NR1—, —O—OC—O—, —CH═CH—, or —C≡C—;
where R1 represents hydrogen or low alkyl, and where r and s each represent a whole number from 0 to 20 on condition that 2≦(r+s)≦20;
R represents a crosslinkable groupwith the structure CH2═CHCOO—, CH2═C(CH3)—COO—, CH2═C(Cl)COO—, CH2═C(Ph)—COO—, CH2═CH—COO—Ph—, CH2═CH—CO—NH—, CH2═C(CH3)—CONH—, CH2═C(Cl)—CONH—, CH2═C(Ph)—CONH—, CH2═C(COOR′)—CH2—COO—, CH2═CH—OOC—, Ph—CH═CH—, CH3—C(═NR′)—, cis or trans-HOOC—R′═CR′—COO—,
Ph reresents phenyl;
R′ represents methyl, ethyl, propyl, butyl or pentyl, and
R″ represents methyl, methoxy, cyano or halogen,
with the proviso that at least one of the ring systems A or B represents a ring system with the formula a1 or a2, at least one of Z1 and Z2 represent a single bond, and —R—S1 and R—S2 do not contain —O—O or —N—O— groups.

10 more elements

A compound of the formula I:

R—S1—A—Z1—B—S2—R I
where
A and B are each independent ring system and each have the formula a1, a2 or b,
whereby, in the trans-1,4-cyclohexylene ring, one or two non-adjacent CH2 groups may be replaced by oxygen, and whereby, in the 1,4-phenylene ring, one or two non-adjacent CH groups may be replaced by nitrogen;
L1, L2, L3 represent, independently, hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkyloxy, C1-C20-alkyloxy carbonyl, formyl, C1-C20-alkyl carbonyl, C1-C20-alkyl carbonyloxy, halogen, cyano or nitro;
Z1, Z2, Z3 represent, independently, a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, —(CH2)4—, —O(CH2)3—, —(CH2)3O— or —C≡C—;
S1, S2 each independently represent a spacer unit;
R represents a crosslinkable group with the structure CH2═CHCOO—, CH2═C(CH3)—COO—, CH2═C(Cl)COO—, CH2═C(Ph)—COO—, CH2═CH—COO—Ph—, CH2═CH—CO—NH—, CH2═C(CH3)—CONH—, CH2═C(Cl)—CONH—, CH2═C(Ph)—CONH—, CH2═C(COOR′)—CH2—COO—, CH2═CH—OOC—, Ph—CH═CH—, CH3—C(═NR′)—, cis or trans-HOOC—R′═CR′—COO—,
Ph represents phenyl;
R′ represents methyl, ethyl, propyl, butyl or pentyl, and
R″ represents methyl, methoxy, cyano or halogen,
with the proviso that at least one of the ring systems A or B represents a ring system with the formula a1 or a2, at least one of Z1 and Z2 represent a single bond, and —R—S1 and R—S2 do not contain —O—O or —N—O— groups, wherein the compound is a compound of the formula I-A, I-B, I-C, I-D, I-E, or I-F:
wherein, one or two non-adjacent CH2 groups of the trans-1,4-cyclohexylene ring may be replaced by oxygen and one or two non-adjacent CH groups of the 1,4-phenylene ring may be replaced by nitrogen;
L11, L12, L13 represent, independently, hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkoxy, C1-C20-alkoxycarbonyl, formyl, C1-C20-alkylcarbonyl, C1-C20-alkylcarbonyloxy, halogen, cyano or nitro;
Z4 represents a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, —(CH2)4—, —O(CH2)3—, —(CH2)3O— or —C≡C—;
and
Z5 represents a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, or —C≡C—.

14 more elements

A compound of the formula I:

R—S1—A—Z1—B—S2—R I
where A and B are each an independent ring system and each have the formula a1, a2 or b,
whereby, in the trans-1,4-cyclohexylene ring, one or two non-adjacent CH2 groups may be replaced by oxygen, and whereby, in the 1,4-phenylene ring, one or two non-adjacent CH groups may be replaced by nitrogen;
L1, L2, L3 represent, independently, hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkyloxy, C1-C20-alkyloxy carbonyl, formyl, C1-C20-alkyl carbonyl, C1-C20-alkyl carbonyloxy, halogen, cyano or nitro;
Z1, Z2, Z3 represent, independently, a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, —(CH2)4—, —O(CH2)3—, —(CH2)3O— or —C≡C—;
S1, S2 each independently represent a spacer unit;
R represents a crosslinkable group with the structure CH2═CHCOO—, CH2═C(CH3)—COO—, CH2═C(Cl)COO—, CH2═C(Ph)—COO—, CH2═CH—COO—Ph—, CH2═CH—CO—NH—, CH2═C(CH3)—CONH—, CH2═C(Cl)—CONH—, CH2═C(Ph)—CONH—, CH2═C(COOR′)—CH2—COO—, CH2═CH—OOC—, Ph—CH═CH—, CH3—C(═NR′)—, cis or trans-HOOC—R′═CR′—COO—,
Ph represents phenyl;
R′ represents methyl, ethyl, propyl, butyl or pentyl, and
R″ represents methyl, methoxy, cyano or halogen,
with the proviso that at least one of the ring systems A or B represents a ring system with the formula a1 or a2, at least one of Z1 and Z2 represent a single bond, and —R—S1 and R—S2 do not contain —O—O or —N—O— groups, wherein the compound is a compound of the formula I-A-1 or I-A-2
where
L11, L12, L13 each represent, independently, hydrogen, C1-C12-alkykl, C1-C12-alkenyl, C1-C12-alkoxy, C1-C12-alkoxycarbonyl, formyl, C1-C12-alkylcarbonyl, C1-C12-alkylcarbonyloxy, fluorine, chlorine, cyano or nitro;
Z4 represents —CH2CH2—, —OCH2, —COO— or —OOC—;
Z5 represents a single bond, —CH2CH2—, —COO— or —OOC—, or —C≡C—;
R represents a crosslinkable groups with the structure CH2═CH—, CH2═CHCOO—, CH2═C(CH3)—COO—, CH2═C(Cl)COO—, or
and
m, n each represent, indepoendently, a whole number from 2 to 20.

15 more elements

A crosslinkable, liquid crystalline mixture, which comprises at least two components, wherein at least one of the components is a crosslinkable compound of the formula I

R—S1—A—Z1—B—S2—R I
where
A and B are each an independent ring system and each have the formula a1, a2 or b,
whereby, in the trans-1,4-cyclohexylene ring, one or two non-adjacent CH2 groups may be replaced by oxygen, and whereby, in the 1,4-phenylene ring, one or two non-adjacent CH groups may be replaced by nitrogen;
L1, L2, L3 represent, independently, hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkyloxy, C1-C20-alkyloxy carbonyl, formyl, C1-C20-alkyl carbonyl, C1-C20-alkyl carbonyloxy, halogen, cyano or nitro;
Z1, Z2, Z3 represent, independently, a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OOC—, —(CH2)4—, —O(CH2)3—, —(CH2)3O— or —C≡C—;
S1, S2 each independently reopresent a spacer unit;
R represents a crosslinkable group with the structure CH2═CH—, CH2═CHCOO—, CH2═C(CH3)—COO—, CH2═C(Cl)COO—, CH2═C(Ph)—COO—, CH2═CH—COO—Ph—, CH2═CH—CO—NH—, CH2═C(CH3)—CONH—, CH2═C(Cl)—CONH—, CH2═C(Ph)—CONH—, CH2═C(COOR′)—CH2—COO—, CH2═CH—O—, CH2═CH—OOC—, Ph—CH═CH—, CH3—C(═NR′)—, cis or trans-HOOC—R′═CR′—COO—,
Ph represents phenyl;
R′ represents methyl, ethyl, propyl, butyl or pentyl, and
R″ represents methyl, methoxy, cyano or halogen,
with the proviso that at least one of the ring systems A or B represents a ring system with the formula a1 or a2, at least one of Z1 and Z2 represent a single bond, and —R—S1 and R—S2 do not contain —O—O or —N—O— groups, which also comprises one or more compounds from the group of formulae
where
X represents hydrogen, C1-C20-alkyl, C1-C20-alkenyl, C1-C20-alkyoxy, C1-C20-alkyoxy carbonyl, formyl, C1-C20-alkyl carbonyl, C1-C20-alkyl carbonyloxy, halogen, cyan or nitro;
m′ represents a whole number from 2 to 20;
t represents a whole number from 2 to 12;
Z represents —COO—, —OOC—, —OCH2—, —CH2O—, —O(CH2)3—, —OOC(CH2)2—, or —COO(CH2)3—;
D represents 1,4-phenylene, trans-1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or trans-1,4-cyclohexylene-1,4-phenylene;
E represents 1,4-phenylene, or 2- or 3-fluoro-1,4-phenylene;
S′ represents —(CH2)m′— or —O(CH2)m′—;
Ra represents a crosslinkable group with the structure CH2═CH—, CH2═CH—COO—, CH2═C(CH3)—COO—, CH2═C(Cl)—COO—, or

18 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/443,214Filed 19 Nov 1999 · continuation
Priority: EP 9710825922 May 1997
Granted: 28 May 2002
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07C 69/92
Of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic…
C07C 69/54
Monocarboxylic acid esters having only one carbon-to-carbon double bond: acrylic acid esters; Methacrylic acid esters
C07C 69/94
Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring: of polycyclic hydroxy carboxylic acids,…
C09K 19/3059
Cyclohexane rings: in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds