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WO2011012315A1 - Matériau piézochrome, matériau composite piézochrome et capteur piézochrome - Google Patents

Matériau piézochrome, matériau composite piézochrome et capteur piézochrome Download PDF

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Publication number
WO2011012315A1
WO2011012315A1 PCT/EP2010/004679 EP2010004679W WO2011012315A1 WO 2011012315 A1 WO2011012315 A1 WO 2011012315A1 EP 2010004679 W EP2010004679 W EP 2010004679W WO 2011012315 A1 WO2011012315 A1 WO 2011012315A1
Authority
WO
WIPO (PCT)
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.)
Ceased
Application number
PCT/EP2010/004679
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German (de)
English (en)
Inventor
Arno Seeboth
Ralf Ruhmann
Renate Vetter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV filed Critical Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Priority to EP10742736A priority Critical patent/EP2459677A1/fr
Publication of WO2011012315A1 publication Critical patent/WO2011012315A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Nonlinear Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Business, Economics & Management (AREA)
  • Accounting & Taxation (AREA)
  • Finance (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.
PCT/EP2010/004679 2009-07-30 2010-07-30 Matériau piézochrome, matériau composite piézochrome et capteur piézochrome Ceased WO2011012315A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10742736A EP2459677A1 (fr) 2009-07-30 2010-07-30 Matériau piézochrome, matériau composite piézochrome et capteur piézochrome

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009035363.1 2009-07-30
DE102009035363A DE102009035363A1 (de) 2009-07-30 2009-07-30 Piezochromes Material, piezochromer Verbundwerkstoff und piezochromer Sensor

Publications (1)

Publication Number Publication Date
WO2011012315A1 true WO2011012315A1 (fr) 2011-02-03

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EP (1) EP2459677A1 (fr)
DE (1) DE102009035363A1 (fr)
WO (1) WO2011012315A1 (fr)

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WO2012118487A1 (fr) * 2011-03-01 2012-09-07 Colgate-Palmolive Company Brosse à dents comprenant un dispositif pour indiquer la force de brossage
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
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