EP2459677A1 - Matériau piézochrome, matériau composite piézochrome et capteur piézochrome - Google Patents
Matériau piézochrome, matériau composite piézochrome et capteur piézochromeInfo
- Publication number
- EP2459677A1 EP2459677A1 EP10742736A EP10742736A EP2459677A1 EP 2459677 A1 EP2459677 A1 EP 2459677A1 EP 10742736 A EP10742736 A EP 10742736A EP 10742736 A EP10742736 A EP 10742736A EP 2459677 A1 EP2459677 A1 EP 2459677A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- piezochromic
- material according
- meth
- acrylate
- piezochrome
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000463 material Substances 0.000 title claims abstract description 55
- 239000002131 composite material Substances 0.000 title claims abstract description 24
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 25
- 239000013543 active substance Substances 0.000 claims abstract description 20
- 229920006254 polymer film Polymers 0.000 claims abstract description 15
- 239000011159 matrix material Substances 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- 238000005516 engineering process Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 19
- 239000004971 Cross linker Substances 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- -1 p-ethoxybenzylidene Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 11
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 235000012000 cholesterol Nutrition 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- DMJDEZUEYXVYNO-DHZHZOJOSA-N (e)-3-(4-phenylphenyl)prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C1=CC=CC=C1 DMJDEZUEYXVYNO-DHZHZOJOSA-N 0.000 claims description 3
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 claims description 3
- 229930184652 p-Terphenyl Natural products 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
- 235000021286 stilbenes Nutrition 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- DKSFZDGJNIPROA-UHFFFAOYSA-N (4-octan-2-yloxycarbonylphenyl) 4-hexanoylbenzoate Chemical compound CC(CCCCCC)OC(C1=CC=C(C=C1)OC(C1=CC=C(C=C1)C(CCCCC)=O)=O)=O DKSFZDGJNIPROA-UHFFFAOYSA-N 0.000 claims 1
- 210000003918 fraction a Anatomy 0.000 claims 1
- 230000000694 effects Effects 0.000 description 7
- DBOAVDSSZWDGTH-UHFFFAOYSA-N n-(4-butylphenyl)-1-(4-ethoxyphenyl)methanimine Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OCC)C=C1 DBOAVDSSZWDGTH-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- MGRRGKWPEVFJSH-UHFFFAOYSA-N 10-(10-oxoanthracen-9-ylidene)anthracen-9-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC=C2C1=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MGRRGKWPEVFJSH-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 230000001980 ionochromic effect Effects 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- PLGPDUBTEHIWRH-UHFFFAOYSA-N (4-octan-2-yloxycarbonylphenyl) 4-hexoxybenzoate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)OC1=CC=C(C(=O)OC(C)CCCCCC)C=C1 PLGPDUBTEHIWRH-UHFFFAOYSA-N 0.000 description 1
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- RFKWIEFTBMACPZ-UHFFFAOYSA-N 3-dodecylthiophene Chemical compound CCCCCCCCCCCCC=1C=CSC=1 RFKWIEFTBMACPZ-UHFFFAOYSA-N 0.000 description 1
- SXXWAWNPJCEOGD-UHFFFAOYSA-N 9-xanthen-9-ylidenexanthene Chemical group C12=CC=CC=C2OC2=CC=CC=C2C1=C1C2=CC=CC=C2OC2=CC=CC=C21 SXXWAWNPJCEOGD-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 206010011985 Decubitus ulcer Diseases 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- XMPIMLRYNVGZIA-CCEZHUSRSA-N [10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] [(e)-octadec-9-enyl] carbonate Chemical compound C12CCC3(C)C(C(C)CCCC(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)OCCCCCCCC/C=C/CCCCCCCC)C2 XMPIMLRYNVGZIA-CCEZHUSRSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001841 cholesterols Chemical class 0.000 description 1
- UVZUFUGNHDDLRQ-LLHZKFLPSA-N cholesteryl benzoate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)C1=CC=CC=C1 UVZUFUGNHDDLRQ-LLHZKFLPSA-N 0.000 description 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical class [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- CJADAVIATOALFB-UHFFFAOYSA-N helianthrone Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=C2C3=C1C=CC=C3C(=O)C1=CC=CC=C12 CJADAVIATOALFB-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000004038 photonic crystal Substances 0.000 description 1
- 125000005506 phthalide group Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
- B42D25/00—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof
- B42D25/20—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof characterised by a particular use or purpose
- B42D25/28—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof characterised by a particular use or purpose for use in medical treatment or therapy
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
- B42D25/00—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof
- B42D25/20—Information-bearing cards or sheet-like structures characterised by identification or security features; Manufacture thereof characterised by a particular use or purpose
- B42D25/29—Securities; Bank notes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/36—Steroidal liquid crystal compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01L—MEASURING FORCE, STRESS, TORQUE, WORK, MECHANICAL POWER, MECHANICAL EFFICIENCY, OR FLUID PRESSURE
- G01L1/00—Measuring force or stress, in general
- G01L1/24—Measuring force or stress, in general by measuring variations of optical properties of material when it is stressed, e.g. by photoelastic stress analysis using infrared, visible light, ultraviolet
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/0128—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on electro-mechanical, magneto-mechanical, elasto-optic effects
- G02F1/0131—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on electro-mechanical, magneto-mechanical, elasto-optic effects based on photo-elastic effects, e.g. mechanically induced birefringence
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/1313—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells specially adapted for a particular application
-
- B42D2033/12—
-
- B42D2033/26—
Definitions
- the present invention relates to a piezochromic material consisting essentially of a matrix of a polymer or copolymer in which a liquid crystal and a chirally optically active substance are distributed.
- the present invention relates to a piezochromic composite material in which a layer of the aforementioned piezochromic material is embedded between two polymer films.
- the piezochromic material or the composite material are used primarily in the field of sensors. The need for geometrically deformable sensors to visualize low pressure changes in the real life area, ie below 50 bar, is enormous and continues to increase steadily. Piezochrome effects based on changeable lattice structures in inorganic crystals or absorption effects in organic systems offer so far no solution approach.
- Piezochromes by modification changes in inorganic crystals such. B. in LiF or NaCl
- Liquid crystals such as biphenyls or cholesterol derivatives are used and as piezochrome components xanthenes, diflavines, dianthrones, phthalocyanine-cobalt complexes or spiropyranes are used. Pressures between 1450 psi (99.9 bar) and 15000 psi (1034 bar) should be detectable.
- piezochromic materials refer to use as a security feature in banknotes such as
- the piezochromic system consists of an ionochromic substance and a developer, whereby an electron donor system is formed.
- the piezochrome material can be applied as a color print on banknotes and serves accordingly as a security feature.
- ionochromic substances pH-sensitive dyes or leuco dyes are used. Specifically named are substances like
- Phthalide derivatives derivatives of imidazole, pyrrole, bianthrone, xanthylidenanthrone, dixanthylene or Helianthrone.
- piezochromic substances based on hydroxycarboxylic acids or indolinospirobenzo-thiopyran derivatives are favored.
- FR 2698390 A1 as in WO / 2005/092995, a piezochromic material is likewise described as a security feature for banknotes.
- the films with a layer thickness of 0.8 - 2 mm consist of a polymer matrix and a liquid crystal. Suitable matrix components are polyester, cellulose, polyurethane,
- the liquid crystal has a cholesterol structure. Numerical values for the pressure are not specified.
- the known inorganic as well as organic materials can not be used as piezochromic sensors under realistic conditions under pressure changes significantly below 50 bar. Accordingly, the previously known piezochromic materials can not be used as a security feature in bank notes or in medical technology as a visual pressure sensor for prostheses, dialysis machines, decubitus prophylaxis or compression dressings. The same applies to the simplest visual color sensors which are intended to detect pressure or mechanical deformation (destruction) in packaging materials or in smart labeis (security ID).
- Object of the present invention is therefore, a develop piezochromic material, which at low pressure - below 50 bar - provides a clear optical signal to the human eye and which is mechanically deformable, so that an application in the above areas is possible.
- a piezochromic material which comprises a matrix of at least one polymer and / or copolymer in which at least one liquid crystal and at least one chirally opaquently active substance are distributed.
- a chirally optically active substance is understood according to the invention to mean a component with chiral (helical) properties.
- the resulting continuously twisted optical medium acts as a one-dimensional photonic crystal.
- the at least one liquid crystal is selected from the group consisting of N- (p-ethoxybenzylidene) -pn-butylaniline, N- (p-methoxybenzylidene) -pn-butylaniline, 4-n-alkylbenzoic acid (4-alkylphenyl ) Cholesteryl benzoate, cholesterol, tolane, alkanoic acids, stilbene, azobenzene, 4-phenylcinnamic acid, p-terphenyl, 1, 2-bisbenzoethylene and / or mixtures thereof.
- At least one chirally optically active substance in particular compounds selected from the group consisting of 4- (4-hexyloxybenzoyloxy) benzoate, cholesteryl derivatives and / or mixtures are suitable.
- Poly (meth) acrylates and / or copoly (meth) acrylates are preferably composed of at least one monofunctional monomer and / or at least one polyfunctional one
- the monomer selected from the group consisting of benzyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, methoxyethyl (meth) acrylate, octadecyl (meth) acrylate and / or mixtures thereof is advantageous.
- preferred crosslinkers are selected from the group consisting of 1,4-butanediol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, bisphenol A glycerolate (1-glycerol) phenoldiarcrylate and / or mixtures thereof.
- Advantageous material properties are obtained when the weight ratio between crosslinker and monomer is between 0.01 and 0.8, preferably between 0.1 and 0.6, particularly preferably between 0.2 and 0.4.
- the piezochromic material it is kart if the weight fraction of the liquid crystal, based on the polymer matrix up to 90 wt .-%, preferably between 15 and 60 wt .-%, particularly preferably between 25 and 32 wt .-% is.
- the content of the optically active substance, based on the matrix is preferably up to 10% by weight, preferably between 0.1 and 2.5% by weight, particularly preferably between 0.15 and 0.55% by weight.
- the piezochrome material is in the form of an elastic and highly ordered system, which preferably has a helical structure.
- the piezochromic material according to the invention is further preferably characterized in that a perceptible color change perceptible to the human eye occurs with pressure changes of less than 100 bar, preferably less than 50, particularly preferably less than 10 bar.
- a piezochromic composite comprising a layer of the piezochromic material of any one of the preceding claims, wherein on at least one side, preferably on both sides of the layer of the piezochromic material, a polymer film is applied, preferably of polyolefins, polyesters, polyvinyl chloride and / or polyamides is formed.
- the piezochromic material preferably has a layer thickness of the piezochromic material between 5 ⁇ m to 1 mm, particularly preferably between 5 ⁇ m to 100 ⁇ m.
- Preferred layer thicknesses of the used Polymer film lie between 5 .mu.m and 100 .mu.m, preferably between 10 .mu.m and 30 .mu.m.
- the polymer film has, at least on the side which is brought into contact with the piezochromic material, an orientation layer suitable for liquid crystals.
- This can also be monomolecular. This is a mature technology used for decades in the manufacture of LCDs. This is prior art, U.S. 4,278,326;
- the orientation layer stabilizes the supramolecular helical structure during the polymerization; it should be applied to at least one of the two polymer layers.
- the formation of a stable lattice structure, which is achieved by the crosslinking between the monomers and crosslinkers in the system, is a prerequisite for long-term stability and high switching rates between the different pressure states.
- the Polymer film with its orientation layer for the functionality no longer required. It can, if that is technologically advantageous, be removed. This may be the case if the
- the piezochrome composite system can be easily and reproducibly produced.
- the mixture of liquid crystal and optically active substance is first prepared, which already leads to the formation of a helical structure, which can be characterized well in polarized light.
- the addition of the monomer and the crosslinker takes place.
- the addition can be done sequentially or as a mixture of monomer and crosslinker.
- the initiator is usually added as the last component.
- Polymer films are preferably polyolefins (PE and PP, also the cyclic form Zeonor), polyester, polyvinyl chloride or polyamide used.
- the mixture obtained is applied to a polymer film in layers following the mixing steps a) to c) of the process described above, preferably between two polymer films and subsequently by exposure to temperature and / or light and / or polymerized by chemical initiation.
- a piezochromic sensor is provided, which has a previously stated
- piezochromic material or a piezochromic composite material.
- the piezochromic materials and / or the piezochromic composites are used in particular as a security feature in banknotes; as a pressure sensor, in particular in medical technology; as part of an optical, electrical, opto-electric, piezochromic and / or chromogenic module.
- Crosslinking agents 1,4-butanediol diaccylate (BDA, Aldrich), polyethylene glycol diacrylate (PEG-DA, M700, Aldrich), 1,10-decanediol diacrylate (DDA, Aldrich) - optically active substance: 4- (4- Hexyloxybenzoyl oxy) benzoate (S811, Merck), cholesteryl derivative (Aldrich)
- Photoinitiator Genocure LTM (Rahn), Daracure, Irgacure (Ciba), Lucerin (BASF)
- Ethoxybenzylidene) -pn-butylaniline (EBBA, Riedel-De Haen) or N- (p-methoxybenzylidene) -pn-butylaniline (MBBA, Riedel-De Haen) or derivatives of 4-n-alkylbenzoic acid ( 4-alkylphenyl ester) n,
- Alkanoic acids stilbene, azobenzene, 4-phenylcinnamic acid, p-terphenyl, or for example 1, 2-bis benzoyläthen.
- the weight fractions of the initiator and the optically active substance in the composite system are preferably below 10%. It should be noted at this point that the molecular ratio of the individual substances to one another is important for the functioning of the piezochromic material.
- the crosslinker is preferably present at up to 20%; Monomer and
- Liquid crystal preferably each with up to 90%.
- the piezochromic effect becomes visible at a pressure of less than 50 bar.
- the composite consists of at least one monomer, one
- Crosslinker a photoinitiator, a liquid crystal and an optically active substance. It is explicitly pointed out that the resulting macroscopic properties do not derive linearly from the individual materials used.
- the newly formed supramolecular elastic system has unique physicochemical properties. Of particular advantage is a helical structure.
- the switching speed between the different colors as a function of the pressure change is preferably in the second range. Above all, it can be controlled by the proportion of crosslinker in the system. At high crosslinker content, the back reaction can also be in the minutes range or even higher.
- Piezochrome layers with a thickness of between 5 ⁇ m and 100 ⁇ m can be produced as described above. If necessary, the layer thickness can also be greater, but this is the case for the piezochromic effect. is not necessary.
- Component A The liquid-crystal mixture E5 (mixture consisting of four components of alkylcyanobiphenyl derivatives and one component of alkoxycyano-biphenyl derivative) is admixed with the optically active substance S-811 in a proportion by weight of 22%.
- the mixture is heated to 58 ° C. above the clearing point of the E5 component and then cooled again at room temperature.
- Component B 34% by weight DDA is doped to the monomer BzMA.
- the mixture is heated at 60 ° C. for 25 minutes.
- the mixtures A and B are mixed in a ratio of 1: 2.4 at a temperature between 50 ° C and 55 ° C.
- 0.2% by weight of Genocure LTM polymerization initiator is added.
- the piezochromic material thickens with a layer thickness of 25 ⁇ m between two 15 ⁇ m each
- Example 2 Component A: To the liquid crystal EBBA, the optically active substance cholesteryloleyl carbonate is doped with 27% by weight. The mixture is heated above the clear point of EBBA to 52 ° C. Component B: To the monomer ODA is doped 28% by weight of the crosslinker PEG-DA, M70, the mixture being heated to 55 ° C.
- the mixtures A and B are mixed in a ratio of 1: 1.9 at a temperature between 45 ° C and
- the piezochromic material is mounted with a layer thickness of 30 ⁇ m between each two 12 ⁇ m thick Zeonorfolien. Both Zeonor foils are mixed with a maleic anhydride
- Styrene copolymer orientation layer (less than 1 micron) provided.
- the system is polymerized in UV light for 20 minutes; then the Zeonor foil can be easily removed.
- Component A To a liquid crystal mixture consisting of EBBA and MBBA in the ratio 3: 1, the optically active substance S-811 (4- [[4- (hexyloxy) benzoyl] oxy] benzoic acid 2-octyl ester) is doped with 30 weight percent, wherein the temperature is above 50 0 C and the duration of at least 8 min. is.
- Component B To the monomer MEA, 22% by weight of a crosslinker mixture consisting of BDA: DDA in a ratio of 1: 2.5 is mixed. The temperature here is between 50 0 C and 55 ° C. Daracur at 0.4% by weight is used as a photoinitiator for the subsequent polymerization.
- piezochrome material is thick with a thickness of 50 microns between two each 20 microns
- lecithin-coated PE films were additionally rubbed in the direction of the dipping process.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Finance (AREA)
- Business, Economics & Management (AREA)
- Accounting & Taxation (AREA)
- Polarising Elements (AREA)
Abstract
La présente invention concerne un matériau piézochrome qui est constitué sensiblement d'une matrice en polymère ou copolymère, dans laquelle sont répartis un cristal liquide et une substance chirale optiquement active. L'invention concerne également un matériau composite piézochrome constitué d'une couche, du matériau piézochrome susmentionné, enrobée entre deux films polymères. Le matériau piézochrome et le matériau composite trouvent une application surtout dans le domaine de la technologie des capteurs.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009035363A DE102009035363A1 (de) | 2009-07-30 | 2009-07-30 | Piezochromes Material, piezochromer Verbundwerkstoff und piezochromer Sensor |
PCT/EP2010/004679 WO2011012315A1 (fr) | 2009-07-30 | 2010-07-30 | Matériau piézochrome, matériau composite piézochrome et capteur piézochrome |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2459677A1 true EP2459677A1 (fr) | 2012-06-06 |
Family
ID=43128298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP10742736A Withdrawn EP2459677A1 (fr) | 2009-07-30 | 2010-07-30 | Matériau piézochrome, matériau composite piézochrome et capteur piézochrome |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP2459677A1 (fr) |
DE (1) | DE102009035363A1 (fr) |
WO (1) | WO2011012315A1 (fr) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101562721B1 (ko) * | 2011-03-01 | 2015-10-22 | 콜게이트-파아므올리브캄파니 | 칫솔질 힘을 표시하기 위한 장치를 포함하는 칫솔 |
EP3284993A1 (fr) | 2016-08-16 | 2018-02-21 | Masterflex SE | Tuyaux flexible comprenant un materiel de detection integre |
EP3501324A1 (fr) * | 2017-12-21 | 2019-06-26 | The Swatch Group Research and Development Ltd | Élément d'habillage pour pièce d'horlogerie ou de bijouterie |
DE102018222633A1 (de) | 2018-12-20 | 2020-06-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Fingersegment für einen Handschuh |
DE102020210756A1 (de) | 2020-08-25 | 2022-03-03 | B. Braun Melsungen Aktiengesellschaft | Medizinische Vorrichtung zum visuellen Darstellen eines Injektionsdruckes eines Fluides |
DE102022107940A1 (de) | 2022-04-04 | 2023-10-05 | Gilbert Duong | Zahnputznavigationssystem und Verfahren zur Zahnputznavigation |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5314230B2 (fr) | 1973-02-17 | 1978-05-16 | ||
JPS5220847A (en) | 1975-08-09 | 1977-02-17 | Sharp Corp | Base panel for holding liquid crystal |
JPS54121757A (en) | 1978-03-15 | 1979-09-21 | Hitachi Ltd | Liquid crystal display element |
JPS5764209A (en) | 1980-10-07 | 1982-04-19 | Hitachi Ltd | Liquid crystal display element and its manufacture |
DD221024A1 (de) | 1983-12-22 | 1985-04-10 | Werk Fernsehelektronik Veb | Farbige fluessigkristallanzeige |
DD252449A1 (de) | 1986-09-04 | 1987-12-16 | Werk Fernsehelektronik Veb | Verfahren zur orientierung von fluessigkristallen |
JP3030471B2 (ja) | 1991-03-13 | 2000-04-10 | 大塚化学株式会社 | インドリノスピロベンゾチオピラン誘導体とその開環型異性体を含むことからなる結晶、その製造方法及び該結晶からなるピエゾクロミック材料 |
US6104448A (en) * | 1991-05-02 | 2000-08-15 | Kent State University | Pressure sensitive liquid crystalline light modulating device and material |
KR100320567B1 (ko) * | 1992-05-18 | 2002-06-20 | 액정광변조장치및재료 | |
FR2698390B1 (fr) | 1992-11-20 | 1994-12-23 | Arjo Wiggins Sa | Document de sécurité authentifiable par effet piezooptique. |
GB9902080D0 (en) | 1999-01-29 | 1999-03-24 | Unilever Plc | Toothbrush |
NL1012463C2 (nl) | 1999-06-29 | 2001-01-02 | Meyn Food Proc Technology Bv | Inrichting voor het lossnijden van de aars van geslacht gevogelte. |
MXPA04010175A (es) | 2002-04-18 | 2005-02-03 | Stowe Woodward Llc | Rodillo con cubierta indicadora de tension y/o temperatura. |
DE10312464A1 (de) * | 2003-03-20 | 2004-09-30 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Zusammensetzung zur Herstellung eines Duroplasten mit thermochromen Eigenschaften |
JP2007528929A (ja) | 2004-03-12 | 2007-10-18 | サン・ケミカル・コーポレーション | 可逆性感圧変色システム |
US7576829B2 (en) * | 2004-03-19 | 2009-08-18 | Japan Science And Technology Agency | Liquid crystal display device |
US7652731B2 (en) * | 2006-05-16 | 2010-01-26 | Kent State University | Polymer enhanced cholesteric electro-optical devices |
EP2137271A1 (fr) * | 2007-03-13 | 2009-12-30 | Technische Universiteit Eindhoven | Mélange cristallin liquide polymérisable approprié pour le jet d'encre |
US7648647B2 (en) * | 2007-05-08 | 2010-01-19 | Kyushu University, National University Corporation | Polymer/liquid crystal composite and liquid crystal element |
JP2010531468A (ja) * | 2007-06-25 | 2010-09-24 | ヴライト イノヴェーションズ リミテッド | 高分子分散液晶構造 |
-
2009
- 2009-07-30 DE DE102009035363A patent/DE102009035363A1/de not_active Withdrawn
-
2010
- 2010-07-30 EP EP10742736A patent/EP2459677A1/fr not_active Withdrawn
- 2010-07-30 WO PCT/EP2010/004679 patent/WO2011012315A1/fr active Application Filing
Non-Patent Citations (1)
Title |
---|
See references of WO2011012315A1 * |
Also Published As
Publication number | Publication date |
---|---|
DE102009035363A1 (de) | 2011-02-03 |
WO2011012315A1 (fr) | 2011-02-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2011012315A1 (fr) | Matériau piézochrome, matériau composite piézochrome et capteur piézochrome | |
DE60212183T2 (de) | Verfahren zur herstellung eines verbundes | |
DE69836228T2 (de) | Zusammengesetzter, phasenseparierter organischer film und dessen herstellung | |
EP2818919B1 (fr) | Méthode pour produire une encre d'imprimerie piezochromique, encre d'imprimerie piezochromique, et méthode pour produire un élément de sécurité piézochrome | |
DE69310442T2 (de) | Flüssigkristallverbundschicht vom Dispersions-typ, deren Herstellungsverfahren sowie in ihr zu verwendendes Flüssigkristallmaterial | |
DE3854910T2 (de) | Flüssigkristallvorrichtung | |
EP0622789B1 (fr) | Structures encouche contenant des polymères à chaíne latérale | |
DE69733987T2 (de) | Kompensator | |
DE69612609T3 (de) | Polymerischer film | |
WO2000037585A1 (fr) | Utilisation de substances polymerisables a cristaux liquides pour la fabrication de composants optiques | |
DE69716357T2 (de) | Schaltbare Flüssigkristallvorrichtung und Verfahren zu deren Herstellung | |
DE4008525C2 (fr) | ||
DE19504224A1 (de) | Flüssigkristallines Material | |
DE19623147B4 (de) | Folie, Verfahren zur Herstellung derselben und seine Verwendung in einem Flüssigkristalldisplay | |
DE68917914T2 (de) | Licht modulierende materialien enthaltend flüssigkristallmikrotröpfen dispergiert in einer polymermatritze. | |
EP2798397A1 (fr) | Dispositif de régulation en fonction de la température du passage d'énergie à travers une surface transparente | |
DE3020645A1 (de) | Fluessigkristallanzeige und verfahren zu ihrer herstellung | |
DE69308049T2 (de) | Piezoelektrisches Material mit einem polymeren Netzwerk | |
EP1294785A1 (fr) | Copolymeres en bloc pour la memorisation optique de donnees | |
DE3340954A1 (de) | Polymere fluessigkristalle | |
EP1558699A1 (fr) | Melanges polymerisables | |
EP2174183B1 (fr) | Cellule d'affichage dotée d'une couche de cristaux liquides compartimentée, procédé pour sa fabrication et mélange contenant un matériau de cristaux liquides et convenant dans ce but | |
DE69915258T2 (de) | Effiziente photolumineszente polarisatoren, verfahren zu deren herstellung, und ihre anwendung bei anzeigevorrichtungen | |
EP1449283B1 (fr) | Milieu amplificateur pour laser a colorants a solide | |
DE3027571C2 (de) | Flüssigkristallanzeige mit einer orientierenden und polarisierenden Schicht |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20120223 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR |
|
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20170201 |