Dichoric mixture
AssigneeRolic Ltd c/o Rolic Technologies Ltd
InventorsRichard Buchecker, Zoubair M. Cherkaoui, Thomas Peglow, Franco Moia
Life of this patent
Estimating the term…
Abstract
A mesogenic, crosslinkable mixture comprising at least one polymerisable liquid crystal and at least one polymerisable dichroic dye of the general formula (I) wherein A represents a dichroic residue exhibiting at least partial absorption in the visible region >400 nm: n1, n2, n3, n4 signifies 0 or 1 whereby the sum of n1, n2, n3, n4 is >0, and B1 to B4 represent a group of substructure II wherein the broken line symbolizes the linkage to said dichroic residue. 1
Claims63
A mesogenic, crosslinkable mixture comprising at least one polymerisable liquid crystal and at least one polymerisable dichroic dye of the general formula I:
- 24
- wherein
- A represents a dichroic residue exhibiting at least partial absorption in the visible region >400 nm;
- n1, n2, n3, n4 signify 0 or 1, whereby the sum of n1, n2, n3 and n4 is >0, and
- B1 to B4 represent a group of substructure II
- 25
- wherein the broken line symbolises the linkage to said dichroic residue and wherein:
- A1, A2, A3 each independently represent an aromatic or alicyclic group, which is unsubstituted or substituted by fluorine, chlorine, cyano, nitro, or a straight-chain or branched alkyl residue, which is unsubstituted, mono-substituted by cyano or halogeno, or poly-substituted by halogeno, having 1 to 18 carbon atoms, and wherein one or more of the non-adjacent CH2 groups may independently be replaced by Q, whereby Q represents —O—, —CO—, —CO—O—, —O—CO—, —Si(CH3)2—O—Si(CH3)2—, —NR2—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—, —NR2—CO—NR2—, —CH═CH—, —C≡C—, —O—CO—O—, and R2 represents hydrogen or lower alkyl;
- S1, S2 represent a single covalent bond or a spacer unit, such as a straight-chain or branched alkylene residue, which is unsubstituted, mono-substituted by cyano or halogeno, or poly-substituted by halogeno, having 1 to 24 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by Q, wherein Q has the meaning given above;
- Z1, Z2 independently represent a single covalent bond or a spacer unit, such as a straight-chain or branched alkylene residue, which is unsubstituted, mono-substituted by cyano or halogeno, or poly-substituted by halogeno, having 1 to 8 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by Q, —N═N— or —CR2═C—CO—, wherein Q and R2 have the meaning given above;
- P represents a polymerisable group;
- m1, m2, m3 independently are 0 or 1;
- and
- o is 0 or 1, whereby the sum of the symbols o in B1 to B4 is >0.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the alicyclic group is a non-aromatic carbocyclic or heterocyclic ring system having 3 to 10 carbon atoms.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the alicyclic group is cyclopropane, cyclobutane, cyclopentane, cyclopentene, cyclohexane, cyclohexene, cyclohexadiene or decaline.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the straight-chain or branched alkyl group is selected from the group comprising methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 3-methylpentyl, allyl, but-3-en-1-yl, pent-4-en-1-yl, hex-5-en-1-yl, propynyl, butynyl, pentynyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, cyclopentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, 3-methylpentyloxy, allyloxy, but-3-enyloxy, pent-4-enyloxy, cylohexylmethoxy, cyclopentylmethoxy, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, cyclopentyloxycarbonyl, hexyloxycarbonyl, cyclohexyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, 3-methylpentyloxycarbonyl, allyloxycarbonyl, but-3-enyloxycarbonyl, pent-4-enyloxycarbonyl, cylohexylmethoxycarbonyl, cyclopentylmethoxycarbonyl, acetoxy, ethylcarbonyloxy, propylcarbonyloxy, isopropylcarbonyloxy, butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, tert-butylcarbonyloxy, pentylcarbonyloxy, isopentylcarbonyloxy, cyclopentylcarbonyloxy, hexylcarbonyloxy, cyclohexylcarbonyloxy, octylcarbonyloxy, nonylcarbonyloxy, decylcarbonyloxy, undecylcarbonyloxy, dodecylcarbonyloxy, 3-methylpentylcarbonyloxy, but-3-enyloxy, pent-4-enyloxy, acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, pentylcarbonyl, isopentylcarbonyl, cyclohexylcarbonyl, octylcarbonyl, nonylcarbonyl, decylcarbonyl, undecylcarbonyl, dodecylcarbonyl, methoxyacetoxy, 1-methoxy-2-propoxy, 3-methoxy-1-propoxy, 2-methoxyethoxy, 2-isopropoxyethoxy, 1-ethoxy-3-pentyloxy, 3-butynyloxy, 4-pentynyloxy, 5-chloropentynyl, 4-pentynecarbonyloxy, 6-propyloxyhexyl, 6-propyloxyhexyloxy, 2-fluoroethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1H,1 H-pentadecafluorooctyl, 1H,1H,7H-dodecafluoroheptyl, 2-(perfluorooctyl)ethyl, 2-(perfluorobutyl)ethyl, 2-(perfluorohexyl)ethyl, 2-(perfluorodecyl)ethyl, perfluoropropyl, perfluorobutyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, 1-fluoropropoxy, 1-fluoropentyloxy, 2-fluoropropoxy, 2,2-difluoropropoxy, 3-fluoropropoxy, 3,3-difluoropropoxy, 3,3,3-trifluoropropoxy, and trifluoromethoxy.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the lower alkyl is a straight chain or branched hydrocarbon radical having 1 to 6 carbon atoms.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the lower alkyl is a straight chain or branched hydrocarbon radical having 1 to 3 carbon atoms.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the lower alkyl is methyl, ethyl, propyl or isopropyl.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the dichroic dye is an azo dye, an anthraquinone, a benzoquinone, a perylene, an azulene or a merocyanine.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the dichroic dye is a dye comprising azo- or anthraquinone residues.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the sum of substituents B attached to a dichroic residue A expressed by (n1+n2+n3+n4) is preferably ≦3.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the sum of substituents B attached to a dichroic residue A expressed by (n1+n2+n3+n4) is preferably ≦2.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein A1, A2 and A3 independently of each other are unsubstituted, saturated five- or six-membered alicyclic rings or six-membered aromatic rings, optionally substituted by fluorine or chlorine or nitro or by a straight chain or branched alkyl residue, which is unsubstituted, mono- or poly-substituted by fluorine having 1-12 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—, —CH═CH—, —C≡C—, —O—CO—O—, wherein R2 represents hydrogen or lower alkyl.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein A1, A2 and A3 are a unsubstituted cyclopentane-1,3-diyl, unsubstituted cyclohexane-1,4-diyl, or 1,4-phenylene, which is unsubstituted, mono- or poly-substituted by fluorine or chlorine or a straight-chain or branched alkyl residue, which is unsubstituted, mono- or poly-substituted by fluorine having 1-12 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —CH═CH—, —C≡C—.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein S1 and S2 are selected from the group comprising —(CH2)r—, —(CH2)r—O—, —(CH2)r—CO—, —(CH2)r—CO—O—, —(CH2)r—O—CO—, —(CH2)r—CO—NR2—, —(CH2)r—NR2—CO—, —(CH2)r—NR2—, —(CH2)r—O—(CH2)s—, —(CH2)r—CO—O—(CH2)s—, —(CH2)r—O—CO—(CH2)s—, —(CH2)r—NR2—CO—(CH2)s—, —(CH2)r—NR2—CO—O—(CH2)s—, —(CH2)r—O—(CH2)s—O—, —(CH2)r—CO—O—(CH2)s—O—, —(CH2)r—O—CO—(CH2)s—O—, —(CH2)r—NR2—CO—(CH2)s—O —, —(CH2)r—NR2—CO—O—(CH2)s—O—, —O—(CH2)r—, —CO—O—(CH2)r—, —O—CO—(CH2)r—, —NR2—CO—(CH2)r—, —CO—NR2—(CH2)r—, —NR2—(CH2)r—, —O—(CH2)r—CO—O—, —O—(CH2)r—O—CO—, —O—(CH2)r—CO—NR2—, —O—(CH2)r—NR2—, —O—(CH2)r—O—, —O—(CH2)r—NR2—CO—, —NR2—(CH2)r—CO—O—, —NR2—(CH2)r—O—, —NR2—(CH2)r—NR2—, —NR2—(CH2)r—O—CO—, —CO—NR2—(CH2)r—O—, —CO—NR2—(CH2)r—NR2—, —CO—NR2—(CH2)r—O—CO—, —O—CO—(CH2)r—CO—, —O—CO—(CH2)r—O—, —O—CO—(CH2)r—NR2—, —O—CO—(CH2)r—CO—O—, —O—CO—(CH2)r—CO—NR2—, —O—CO—(CH2)r—NR2—CO—, —O—(CH2)r—O—(CH2)s—, —O—(CH2)r—CO—O—(CH2)s—, —O—(CH2)r—NR2—CO—(CH2)s—, —O—(CH2)r—NR2—CO—O—(CH2)s—, —O—(CH2)r—CO—O—(CH2)s—O—, —O—(CH2)r—O—(CH2)s—O—, —O—(CH2)r—NR2—CO—(CH2)s—O—, —O—(CH2)r—NR2—CO—O—(CH2)s—O—, —CO—O—(CH2)r—O—(CH2)s—, —CO—O—(CH2)r—O—(CH2)s—O—, wherein r and s are each an integer from 1 to 20, the sum of r+s≦21, wherein R2 represents hydrogen or lower alkyl, and which are attached to the dichroic residue and the polymerisable group, respectively, such that heteroatoms are not directly linked to each other.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein S1 is selected from the group comprising —(CH2)r—, (CH2)r—O—, —(CH2)r—CO —O—, —(CH2)r—O—CO—, —(CH2)r—CO—NH—, —(CH2)r—NH—CO—, —(CH2)r—NH—CO—(CH2)s—, —(CH2)r—NH—CO—O—(CH2)s—, —(CH2)r—O—(CH2)s—O—, —(CH2)r—NH—CO—(CH2)s—O—, —(CH2)r—NH—CO—O—(CH2)s—O—, —O—(CH2)r—, —CO—O—(CH2)r—, —CO—NH—(CH2)r—, —O—CO—(CH2)r—, —O—CO—(CH2)r—CO—O—, —O—(CH2)r—O—CO—, —O—(CH2)r—CO—NH—, —O—(CH2)r—NH—CO—, —CO—O—(CH2)r—O—, —CO—NH—(CH2)r—O—, —O—(CH2)r—O—, —O—(CH2)r—NH—CO—(CH2)s—, —O—(CH2)r—O—(CH2)s—O—, —O—CO—(CH2)r—O—(CH2)s—O—, —CO—O—(CH2)r—O—(CH2)s—O—, —O—(CH2)r—NH—CO—(CH2)s—O—, —O—CO—(CH2)r—NH—CO—(CH2)s—O—, wherein r and s are each an integer from 1 to 16, the sum of r+s≦18 and which are attached to the dichroic residue and the polymerisable group, respectively, such that heteroatoms are not directly linked to each other.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein S1 selected from the group comprising —(CH2)r—, —(CH2)r—O—, —(CH2)r—CO—O—, —(CH2)r—O—CO—, —(CH2)r—O—(CH2)s—O—, —(CH2)r—NH—CO—O—(CH2)s—O—, and if attached to a carbon atom of the dichroic residue also —O—(CH2)r—, —CO—O—(CH2)r—, —O—CO—(CH2)r—, —O—CO—(CH2)r—CO—O—, —O—(CH2)r—O—CO—, —CO—O—(CH2)r—O—, —O—(CH2)r—O—, —(CH2)r—O—(CH2)s—O—, —O—CO—(CH2)r—O—(CH2)s—O—, —CO—O—(CH2)r—O—(CH2)s—O—, wherein r and s are each an integer from 1 to 12 the sum of r+s≦14, and which are attached to the dichroic residue and the polymerisable group, respectively, such that heteroatoms are not directly linked to each other.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein S1 is selected from the group comprising 1,2-ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, 1,7-heptylene, 1,8-octylene, 1,9-nonylene, 1,10-decylene, 1,11-undecylene, 1,12-dodecylene, 3-methyl-1,4-butylene, 3-propyleneoxy, 3-propyleneoxycarbonyl, 2-ethylenecarbonyloxy, 4-butyleneoxy, 4-butyleneoxycarbonyl, 3-propylenecarbonyloxy, 5-pentyleneoxy, 5-pentyleneoxycarbonyl, 4-butylenecarbonyloxy, 6-hexyleneoxy, 6-hexyleneoxycarbonyl, 5-pentylenecarbonyloxy, 7-heptyleneoxy, 7-heptyleneoxycarbonyvl, 6-hexylenecarbonyloxy, 8-octyleneoxy, 8-octyleneoxycarbonyl, 7-heptylenecarbonyloxy, 9-nonyleneoxy, 9-nonyleneoxycarbonyl, 8-octylenecarbonyloxy, 10-decyleneoxy, 10-decyleneoxycarbonyl, 9-nonylenecarbonyloxy, 11-undecyleneoxy, 11-undecyleneoxycarbonyl, 10-decylenecarbonyloxy, 12-dodecyleneoxy, 12-dodecyleneoxycarbonyl, 11-undecylenecarbonyloxy, 3-propyleneiminocarbonyl, 4-butyleneiminocarbonyl, 5-pentyleneiminocarbonyl, 6-hexyleneiminocarbonyl, 7-heptyleneiminocarbonyl, 8-octyleneiminocarbonyl, 9-nonyleneiminocarbonyl, 10-decyleneiminocarbonyl, 11-undecyleneiminocarbonyl, 12-dodecyleneiminocarbonyl, 2-ethylenecarbonylimino, 3-propylenecarbonylimino, 4-butylenecarbonylimino, 5-pentylenecarbonylirnino, 6-hexylenecarbonylimino, 7-heptylenecarbonylimino, 8-octylenecarbonylimino, 9-nonylenecarbonylimino, 10-decylenecarbonylimino, 11-undecylenecarbonylimino, 6-(3-propyleneirninocarbonyloxy)hexyl, 6-(3-propyleneoxy)hexyl, 6-(3-propyleneoxy)hexyloxy, 6-(3-propyleneiminocarbonyloxy)hexyloxy, 6-(3-propyleneiminocarbonyl)hexyl, 6-(3-propyleneimninocarbonyl)hexyloxy, 1,2-ethylenedioxy, 1,3-propylenedioxy, 1,4-butylenedioxy, 1,5-pentylenedioxy, 1,6-hexylenedioxy, 1,7-heptylenedioxy, 1,8-octylenedioxy, 1,9-nonylenedioxy, 1,10-decylenedioxy, 1,11-undecylenedioxy, and 1,12-dodecylenedioxy.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein Z1 and Z2 groups are a single covalent bond or a straight-chain or branched alkylene residue, which is unsubstituted, mono-substituted or poly-substituted by fluoro, having 1 to 8 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—, —CO—O—, —O—CO—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—, —CH═CH—, —C≡C—, —O—CO—O—, —N═N—, —CR2═C—CO—, wherein R2 represents hydrogen or lower alkyl.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein Z1 and Z2 groups are a single covalent bond or a straight-chain or branched alkylene residue, having 1 to 6 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —CH═CH—, —C≡C—, —O—CO—O—, —N═N—, —CR2═C—CO—, wherein R2 represents hydrogen or lower alkyl.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein Z1 and Z2 groups are a single covalent bond or a straight-chain or branched alkylene residue, having 1 to 4 carbon atoms, wherein one or two of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —N═N—.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the polymerisable groups P are selected from the group of CH2═CW—, CH2═CW—COO—, CH2═CH—CO—NH—, CH2═C(Ph)—CO—NH—, CH2═CH—O—, CH2—═CH—OOC—, Ph—CH═CH—, CH2═CH—Ph—, CH2═CH—Ph—O—, R3—Ph—CH═CH—COO—, R3—OOC—CH═CH—Ph—O—, N-maleinimidyl, wherein
- W is hydrogen, chloro or methyl,
- R3 is lower alkyl or lower alkoxy,
- Ph— is phenyl, and
- —Ph— is 1,4-phenylene.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the polymerisable groups P are CH2═CW—, CH2═CW—COO—, CH2═CH—O— wherein W is hydrogen or methyl.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the number of rings in substructure II expressed by m1+m2+m3 is ≦2.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein at least one of the LCP components comprises more than one polymerisable group.
A mesogenic, crosslinkable mixture according to any preceding claim further comprising isotropic compounds comprising two or more polymerisable groups.
A mesogenic, crosslinkable mixture according to any preceding claim further comprising additives.
A mesogenic, crosslinkable mixture according to any preceding claim, comprising at least one dichroic dye according to the general formula I and at least two polymerisable liquid crystals, wherein at least one of them comprises more than one polymerisable group.
A mesogenic, crosslinkable mixture according to any preceding claim comprising one to four dichroic dyes of formula I and at least two polymerisable liquid crystals comprising each two polymerisable groups.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the total content of dichroic dyes is from 0.1 to 50% wt.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the total content of dichroic dyes is from 0.5 to 30% wt.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the total content the dichroic dyes is from 0.5 to 20% wt.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the dichroic dye is an azo dye of the formulae III-V:
- R4—Ar1—N═N—Ar2—B1 IIIR4—Ar1—N═N—Ar2—N═N—Ar3—B1 IVR4—Ar1—N═N—Ar2—N═N—Ar3—N═N—Ar4—B1 V
- wherein
- R4 represents hydrogen, fluoro, chloro, bromo, cyano, nitro, —NR2R3, a three- to seven-membered cyclic amino group, —CR2═CR3—NO2, —CR2═CR3—CN, —CR2═C(CN)2, or a straight chain or branched alkyl residue, which is unsubstituted, mono- or poly-substituted by fluorine having 1-18 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—,—CH═CH—, —C≡C—, —O—CO—O—, wherein R2 and R3 independently represent hydrogen or lower alkyl;
- Ar1, Ar2, Ar3, Ar4 independently of each other are 1,4-phenylene, 1,4- or 1,5-naphthylene optionally substituted by fluorine, chlorine, hydroxy, —NR2R3 or by a straight chain or branched alkyl residue, which is unsubstituted, mono- or poly-substituted by fluorine having 1-12 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—, —CH═CH—, —C≡C—, —O—CO—O—, wherein R2 and R3 independently represent hydrogen or lower alkyl;
- and
- wherein Ar1 is also a group of formula a) to c)
- 26
- wherein p is an integer of 1 to 3 and R4 of formulae III to V is attached to the nitrogen atom;
- and
- B1 has the meaning given above.
A mesogenic, crosslinkable mixture according to any preceding claim, wherein the dichroic dye is an anthraquinone of the formulae VI-X:
- 27
- wherein one to four hydrogen atoms are substituted by the groups of B1 to B4 either at carbon or nitrogen atoms, and wherein B1 to B4 have the meaning given above, with the provision that at most one of B1 to B4 is attached to the same nitrogen atom.
A dichroic dye of the formulae IV or V:
- R4—Ar1—N═N—Ar2—N═N—Ar3—B1 IVR4—Ar1—N═N—Ar2—N═N—Ar3—N═N—Ar4—B1 V
- wherein
- R4 represents hydrogen, fluoro, chloro, bromo, cyano, nitro, —NR2R3, a three- to seven-membered cyclic amino group, —CR2═CR3—NO2, —CR2═CR3—CN, —CR2═C(CN)2, or a straight chain or branched alkyl residue, which is unsubstituted, mono- or poly-substituted by fluorine having 1-18 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—, —CH═CH—, —C≡C—, —O—CO—O—, wherein R2 and R3 independently represent hydrogen or lower alkyl;
- Ar1, Ar2, Ar3, Ar4 independently of each other are 1,4-phenylene, 1,4- or 1,5-naphthylene optionally substituted by fluorine, chlorine, hydroxy, —NR2R3 or by a straight chain or branched alkyl residue, which is unsubstituted, mono- or poly-substituted by fluorine having 1-12 carbon atoms, wherein one or more of the non-adjacent CH2 groups may independently be replaced by —O—, —CO—O—, —O—CO—, —NR2—CO—, —CO—NR2—, —NR2—CO—O—, —O—CO—NR2—, —CH═CH—, —C≡C—, —O—CO—O—, wherein R2 and R3 independently represent hydrogen or lower alkyl;
- and
- wherein Ar1 is also a group of formula a) to c)
- 28
- wherein p is an integer of 1 to 3 and R4 of formulae III to V is attached to the nitrogen atom;
- and
- B1 represents a group of substructure II
- 29
- wherein the broken line symbolises the linkage to said dichroic residue and wherein:
- A1, A2, A3, S1, S2, Z1, Z2, m1, m2, m3 and o have the same meaning given above, and
- P represents CH2═CW—, CH2═CW—COO—, CH2═CH—CO—NH—, CH2═C(Ph)—CO—NH—, CH2═CH—O—, CH2═CH—OOC—, Ph—CH═CH—, CH2═CH—Ph—O—, R3—Ph—CH═CH—COO—, R3—OOC—CH═CH—Ph—O—, N-maleinimidyl,
- wherein
- W is hydrogen, chloro or methyl,
- R3 is lower alkyl or lower alkoxy,
- Ph— is phenyl, and
- —Ph— is 1,4-phenylene.
A dichroic dye of the formulae VI-X:
- 30
- wherein one to four hydrogen atoms are substituted by the groups of B1 to B4 either at carbon or nitrogen atoms, and wherein
- B1 to B4 represent a group of substructure II
- 31
- wherein the broken line symbolises the linkage to said dichroic residue and wherein:
- A1, A2, A3, S1, S2, Z1, Z2, m1, m2, m3 and o have the same meaning given above, and
- P represents CH2═CW—, CH2═CW—COO—, CH2═CH—CO—NH—, CH2═C(Ph)—CO—NH—, CH2═CH—O—, CH2═CH—OOC—, Ph—CH═CH—, CH2═CH—Ph—O—, R3—Ph—CH═CH—COO—, R3—OOC—CH═CH—Ph—O—, N-maleinimidyl,
- wherein
- W is hydrogen, chloro or methyl,
- R3 is lower alkyl or lower alkoxy,
- Ph— is phenyl, and
- —Ph— is 1,4-phenylene,
- with the provision that at most one of B1to B4 is attached to the same nitrogen atom.
Dependencies are inferred from the claim text.