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US5705093A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermochromic media

Assignee: Merck Patent GmbH
•
Filing: 1994-08-05
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Granted: 1998-01-06
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Expires: 2014-08-05
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Abstract

Abstract An improved ink comprising a thermochromic liquid crystalline media comprising at least one optically inactive nematic component and at least one optically active component, the improvement wherein the optically active component comprises at least one menthol derivative of formula I <IMAGE> I wherein <IMAGE> is 1,4-phenylene optionally substituted by up to 4 methyl group and/or halogen atoms, particularly fluorine atoms or is 1,4 cyclohexylene and MG is a mesogenic group, or forms a mesogenic group together with <IMAGE>

Inventors

  • 👤 David Coates
  • 👤 Alison Linda May
  • 👤 Jacqueline Dawn Percy

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 17:54
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/50; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/3066; C09K19/3068; C09K19/42; C09K19/46; C09K2019/3095; C09K2323/00; C09K2323/06

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 307 words
An improved thermochromic liquid crystalline medium comprising at least one optically inactive nematic component and at least one optically active component, wherein the optically active component comprises at least one compound of formula I having one menthyl group ##STR45## wherein ##STR46## is 1,4-phenylene optionally substituted by 1 to 4 methyl groups, halogen atoms or a combination thereof, or 1,4-cyclohexylene and MG is a group of formula II R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 -- (II) wherein R 1 is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1 to 16 C atoms, wherein one or two nonadjacent CH 2 groups are optionally replaced by --O--, --S--, --CO--O-- or --O--CO--, independently, A 1 and A 2 each independently denote: (a) 1,4-phenylene optionally substituted by 1 to 4 fluorine atoms, in which one or two CH groups may be replaced by N, (b) 1,4-cyclohexylene optionally substituted by --CN or --CH 3 , in which one or two CH 2 groups may be replaced by O, (c) naphthalin-2,5-diyl or piperidin-1,4-diyl, Z 1 and Z 2 are each independently --CO--O--, --O--CO--, --CH 2 O--, --OCH 2 --, --N═CH--, --CH═N--, --CH 2 CH 2 --, --C--C.tbd. or a single bond and m is 0, 1 or 2 and wherein the optically inactive nematic component comprises at least one compound selected from the formula III to VII ##STR47## wherein R 2 and R 3 each independently is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1-16 C atoms, wherein one or two non-adjacent CH 2 groups are optionally replaced by --O--, --S--, --CO--O-- or --O--CO--, independently, R 4 has one of the meanings given for R 2 and R 3 or is halogen or cyano, ##STR48## each independently denote 1,4-phenylene or 1,4-cyclohexylene, n is 1 or 2, and o, p, q are each independently 0, 1 or 2.
Claim 2
Dependent Claim 307 words
An improved thermochromic liquid crystalline medium comprising at least one optically inactive nematic component and at least one optically active component, wherein the optically active component comprises at least one compound of formula I having one menthyl group ##STR45## wherein ##STR46## is 1,4-phenylene optionally substituted by 1 to 4 methyl groups, halogen atoms or a combination thereof, or 1,4-cyclohexylene and MG is a group of formula II R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 -- (II) wherein R 1 is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1 to 16 C atoms, wherein one or two nonadjacent CH 2 groups are optionally replaced by --O--, --S--, --CO--O-- or --O--CO--, independently, A 1 and A 2 each independently denote: (a) 1,4-phenylene optionally substituted by 1 to 4 fluorine atoms, in which one or two CH groups may be replaced by N, (b) 1,4-cyclohexylene optionally substituted by --CN or --CH 3 , in which one or two CH 2 groups may be replaced by O, (c) naphthalin-2,5-diyl or piperidin-1,4-diyl, Z 1 and Z 2 are each independently --CO--O--, --O--CO--, --CH 2 O--, --OCH 2 --, --N═CH--, --CH═N--, --CH 2 CH 2 --, --C--C.tbd. or a single bond and m is 0, 1 or 2 and wherein the optically inactive nematic component comprises at least one compound selected from the formula III to VII ##STR47## wherein R 2 and R 3 each independently is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1-16 C atoms, wherein one or two non-adjacent CH 2 groups are optionally replaced by --O--, --S--, --CO--O-- or --O--CO--, independently, R 4 has one of the meanings given for R 2 and R 3 or is halogen or cyano, ##STR48## each independently denote 1,4-phenylene or 1,4-cyclohexylene, n is 1 or 2, and o, p, q are each independently 0, 1 or 2.
Claim 3
Dependent Claim 9 words
A medium according to claim 1, which is micro-encapsulated.
Claim 4
Dependent Claim 12 words
An electro-optic device containing a liquid crystalline medium according to claim 1.
Claim 5
Dependent Claim 13 words
A temperature indicating device containing a liquid crystalline medium according to claim 1.
Claim 6
Dependent Claim 45 words
A method of surface thermography which includes the step of (a) applying a thin film of a liquid crystalline medium according to claim 1 to a surface, and (b) observing the color of the film in reflection at an angle of 90° to the surface.
Claim 7
Dependent Claim 12 words
A decorative coating or cosmetic containing a medium according to claim 1.
Claim 8
Dependent Claim 118 words
The liquid crystalline medium of claim 1, wherein the compound of formula I is a compound of one of the following formulae I1 to I14: ______________________________________ R.sup.1 --Phe--Phe--COO-Ment I1 R.sup.1 --Cyc--Phe--COO-Ment I2 R.sup.1 --Cyc--Cyc--COO-Ment I3 R.sup.1 --Phe--Phe--Z.sup.2 --Phe--COO-Ment I4 R.sup.1 --Cyc--Phe--Z.sup.2 --Phe--COO-Ment I5 R.sup.1 --Phe--Phe--Phe--COO-Ment I6 R.sup.1 --Cyc--Phe--Phe--COO-Ment I7 R.sup.1 --Cyc--Cyc--Phe--COO-Ment I8 R.sup.1 --PhePheX--COO-Ment I9 R.sup.1 --CycPheX--COO-Ment I10 R.sup.1 --PhePhe--Z.sup.2 --PheX--COO-Ment I11 R.sup.1 --PheXPhe--Z.sup.2 --Phe--COO-Ment I12 R.sup.1 --PhePhePheX--COO-Ment I13 R.sup.1 --PhePheXPhe--COO-Ment I14 ______________________________________ wherein Ment denotes a group of the formula ##STR49## Phe denotes an unsubstituted 1,4-phenylene group, PheX denotes a 1,4-phenylene group substituted by up to four methyl groups, halogen atoms or a combination thereof, Cyc denotes 1,4-cyclohexylene and R 1 and Z 2 are as defined.
Claim 9
Dependent Claim 37 words
The liquid crystalline medium of claim 7, wherein the compound of formula I is of one of the formulae I9 to I14 and contains a PheX group which is 1,4-phenylene substituted by one or two halogen groups.
Claim 10
Dependent Claim 16 words
The liquid crystalline medium of claim 1, wherein R 1 is H or C 1-6 -alkoxy.
Claim 11
Dependent Claim 23 words
The liquid crystalline medium of claim 1, wherein the compound of the formula I has an HTP value of less than 0.5 μm.
Claim 12
Dependent Claim 23 words
The liquid crystalline medium of claim 1 which contains 2 to 80% by weight of one or more compounds of the formula I.
Claim 13
Dependent Claim 59 words
The liquid crystalline medium of claim 1, wherein the optically inactive nematic component comprises a racemic mixture of at least one compound of one of the formulae III to VII having at least one terminal group R 2 , R 3 or R 4 , which is a chiral alkyl or alkoxy group of 4 to 16 carbon atoms.
Claim 14
Dependent Claim 207 words
An improved ink composition comprising a thermochromic liquid crystalline medium comprising at least one optically inactive nematic component and at least one optically active component, the improvement wherein the optically active component comprises at least one menthol derivative of formula I ##STR50## wherein ##STR51## is 1,4-phenylene optionally substituted by 1 to 4 methyl groups, halogen atoms, or a combination thereof, or 1,4-cyclohexylene and MG is a group of formula II R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 -- (II) wherein R 1 is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1 to 16 C atoms, wherein one or two nonadjacent CH 2 groups are optionally replaced by --O--, --S--, --CO--O-- or --O--CO--, independently, A 1 and A 2 each independently denote: (a) 1,4-phenylene optionally substituted by 1 to 4 fluorine atoms, in which one or two CH groups may be replaced by N, (b) 1,4-cyclohexylene optionally substituted by --CN or --CH 3 , in which one or two CH 2 groups may be replaced by O, (c) naphthalin-2,5-diyl or piperidin-1,4-diyl, Z 1 and Z 2 are each independently --CO--O--, --O--CO--, --CH 2 O--, --OCH 2 --, --N═CH--, --CH═N--, --CH 2 CH 2 --, --C.tbd.C-- or a single bond and m is 0, 1 or 2.
Claim 15
Dependent Claim 207 words
An improved ink composition comprising a thermochromic liquid crystalline medium comprising at least one optically inactive nematic component and at least one optically active component, the improvement wherein the optically active component comprises at least one menthol derivative of formula I ##STR50## wherein ##STR51## is 1,4-phenylene optionally substituted by 1 to 4 methyl groups, halogen atoms, or a combination thereof, or 1,4-cyclohexylene and MG is a group of formula II R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 -- (II) wherein R 1 is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1 to 16 C atoms, wherein one or two nonadjacent CH 2 groups are optionally replaced by --O--, --S--, --CO--O-- or --O--CO--, independently, A 1 and A 2 each independently denote: (a) 1,4-phenylene optionally substituted by 1 to 4 fluorine atoms, in which one or two CH groups may be replaced by N, (b) 1,4-cyclohexylene optionally substituted by --CN or --CH 3 , in which one or two CH 2 groups may be replaced by O, (c) naphthalin-2,5-diyl or piperidin-1,4-diyl, Z 1 and Z 2 are each independently --CO--O--, --O--CO--, --CH 2 O--, --OCH 2 --, --N═CH--, --CH═N--, --CH 2 CH 2 --, --C.tbd.C-- or a single bond and m is 0, 1 or 2.
Claim 16
Dependent Claim 112 words
An improved ink composition according to claim 13, wherein the optically inactive nematic medium comprises at least one compound selected from those of the formulae III to VII ##STR52## wherein R 2 and R 3 each independently is hydrogen or a straight-chained or branched alkyl or alkenyl group of 1-16 C atoms, wherein one or two non-adjacent CH 2 groups are optionally replaced by --O-- --S--, --CO--O-- or --O--CO--, independently, R 4 has one of the meanings given for R 2 and R 3 or is halogen or cyano, ##STR53## each independently denote 1,4-phenylene or 1,4-cyclohexylene, n is 1 or 2, and o, p, q are each independently 0, 1 or 2.
Claim 17
Dependent Claim 20 words
An improved composition according to claim 13, wherein said medium comprises 10-30% of at least one compound of formula I.
Claim 18
Dependent Claim 25 words
A substrate coated with a thermochromic ink according to claim 1, wherein said substrate reflects right circular polarized light and absorbs left circular polarized light.
Claim 19
Dependent Claim 25 words
A substrate coated with a thermochromic ink according to claim 1, wherein said substrate reflects left circular polarized light and absorbs right circular polarized light.

References Cited (Backward Citations)

GB1369714A Cited
US4062799A Cited
JPS5740581A Cited
JPS5829876A Cited
JPS611015A Cited
WO1986004328A1 Cited
US5188815A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2001-01-05 2001-07-07 2002-01-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2005-01-05 2005-07-07 2006-01-06 $3760.00 Window Closed / Lapsed
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