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EP2488368B1 - Utilisation de substances de marquage à bandes étroites - Google Patents

Utilisation de substances de marquage à bandes étroites Download PDF

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Publication number
EP2488368B1
EP2488368B1 EP10768457.3A EP10768457A EP2488368B1 EP 2488368 B1 EP2488368 B1 EP 2488368B1 EP 10768457 A EP10768457 A EP 10768457A EP 2488368 B1 EP2488368 B1 EP 2488368B1
Authority
EP
European Patent Office
Prior art keywords
article
process according
methyl
absorption
marker
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.)
Revoked
Application number
EP10768457.3A
Other languages
German (de)
English (en)
Other versions
EP2488368A1 (fr
Inventor
Rüdiger Sens
Thomas Gessner
Erwin Thiel
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.)
BASF SE
Original Assignee
BASF SE
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
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Application filed by BASF SE filed Critical BASF SE
Priority to EP10768457.3A priority Critical patent/EP2488368B1/fr
Publication of EP2488368A1 publication Critical patent/EP2488368A1/fr
Application granted granted Critical
Publication of EP2488368B1 publication Critical patent/EP2488368B1/fr
Revoked legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
    • B41M3/14—Security printing
    • G—PHYSICS
    • G07—CHECKING-DEVICES
    • G07D—HANDLING OF COINS OR VALUABLE PAPERS, e.g. TESTING, SORTING BY DENOMINATIONS, COUNTING, DISPENSING, CHANGING OR DEPOSITING
    • G07D7/00—Testing specially adapted to determine the identity or genuineness of valuable papers or for segregating those which are unacceptable, e.g. banknotes that are alien to a currency
    • G07D7/06—Testing specially adapted to determine the identity or genuineness of valuable papers or for segregating those which are unacceptable, e.g. banknotes that are alien to a currency using wave or particle radiation
    • G07D7/12—Visible light, infrared or ultraviolet radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M1/00—Inking and printing with a printer's forme
    • B41M1/26—Printing on other surfaces than ordinary paper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M3/00—Printing processes to produce particular kinds of printed work, e.g. patterns
    • B41M3/14—Security printing
    • B41M3/144—Security printing using fluorescent, luminescent or iridescent effects
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/0041—Digital printing on surfaces other than ordinary paper

Definitions

  • the present invention relates to methods for detecting marks on articles.
  • Another object of the invention are methods for authenticating objects.
  • US 6,303,213 B1 describes substrates protected by the application of visible information against unauthorized copying.
  • the visible information is applied with the aid of dyes or pigments which have a half-width of less than 150 nm, preferably less than 100 nm, in the reflectance spectrum for the longest wavelength band.
  • dyes or pigments which have a half-width of less than 150 nm, preferably less than 100 nm, in the reflectance spectrum for the longest wavelength band.
  • the value of the absorption in solution can be used for the half-width.
  • US 5,238,903 describes azomethine dyes for thermal printing with a half-width at the absorption maximum of 60 to 80 nm in ethyl acetate solution (Example 1).
  • the absorption maxima of the dyes are between 430 and 620 nm.
  • the security tag is achieved by means of an identification tag containing colorless or faintly colored, IR absorbing dyes.
  • IR absorbing dyes include nitroso, cyanine, iminium, diiminium, dithiolene compounds, phthalocyanines or azo compounds.
  • the printing inks described above contain at least one dye or pigment having at least one absorption maximum in the visible region of the electromagnetic spectrum, which is clearly different from the absorption maxima of the primary colors of the CIEXYZ system and / or an absorption band in the visible region of the electromagnetic spectrum having a half-width of, more preferably less than 1500 cm -1 .
  • Dyes and pigments are selected from the classes of cyanines, quinones, porphyrins, phthalocyanines or the hetero-substituted polycyclic hydrocarbons.
  • An object of the present invention was thus to provide such methods which are easy to apply with higher security against counterfeiting.
  • Expressions of the form C a -C b designate in the context of this invention chemical compounds or substituents with a certain number of carbon atoms.
  • the number of carbon atoms can be selected from the entire range from a to b, including a and b, a is at least 1 and b is always greater than a.
  • Further specification of the chemical compounds or substituents is made by terms of the form C a -C b -V.
  • V here stands for a chemical compound class or substituent class, for example for alkyl compounds or alkyl substituents.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, particularly preferably fluorine or chlorine.
  • UV wavelength range of the electromagnetic spectrum is from 180 to 380 nm. Accordingly, the visible and IR wavelength ranges of the electromagnetic spectrum of 380 to 780 nm and 780 to 1800 nm.
  • the narrow bands have a half width of ⁇ (less than) 1500 cm -1 .
  • the half width of a narrow band is ⁇ (less than) 1200 cm -1 , more preferably ⁇ (less than) 1000 cm -1 , most preferably from 20 to 1000 cm -1 , especially from 20 to 800 cm -1 .
  • the marker remains permanently attached to the article after being brought into contact with the article to be marked.
  • the marker may be attached to or bonded to the article to be marked by chemical bonding or physical forces such as adsorption.
  • a permanent connection is achieved by the marker is connected by an intense interaction with the object to be marked. This intense interaction causes the label to be permanently, i. at least for a period of a few minutes to a few years, preferably from a few days to 25 years, more preferably from one year to 20 years, in particular from one year to 10 years remains associated with the object.
  • An advantage of the method according to the invention is therefore that the marking agents have not only isolated, for example in solution, narrow bands, but also after bringing into contact with the object to be marked, for example after a printing operation.
  • the marker is in contact with an article, e.g. a label, this item itself serving to mark another item by temporarily or permanently attaching it to the other item, e.g. via an adhesive.
  • At least one of the markers has at least two narrow bands with a half-value width of ⁇ 1500 cm -1 and these narrow bands are in the UV and / or visible and / or IR wavelength range of the electromagnetic spectrum.
  • the absorption maximum of at least one narrow band is preferably in the wavelength range from 180 to 1100 nm, particularly preferably in the wavelength range from 350 to 900 nm, very particularly preferably from 350 to 750 nm, in particular from 400 to 750 nm.
  • markers selected from organic dyes or pigments are used, these being ironic bands in contact with the article to be marked.
  • inorganic chromophores are also suitable as markers, for example rare earth or transition metal compounds.
  • the ions of the rare earths are to be mentioned here with often very narrow-band emission lines, which are used for example in fluorescent lamps and in cathode ray tubes. Examples are Y 2 O 3 : Eu complexes, Mg 4 GeO 5 .5F or (Ce, Tb) MgAl 11 O 19 (see Industrial Inorganic Pigments: edited by Gunter Buxbaum and Gerhard Pfaff, WILEY-VCH, pp. 274-275 , third, completely revised and extended edition).
  • the narrow band absorption lines of the holmium oxides used for the spectral calibration are Ho 2 O 3 , furthermore Ho (3+) in LiYF 4 or Nd: YAG compounds.
  • the markers are preferably selected from metal-containing or metal-free phthalocyanines, preferably copper phthalocyanines, silicon phthalocyanines, aluminum phthalocyanines, zinc phthalocyanines, particularly preferably silicon phthalocyanines which are provided with sterically demanding substituents on the silicon atom or the Phthalocyaninchromophors; Cyanine dyes, preferably charged cyanine dyes, more preferably rhodamine, oxazine or pseudoisocyanine dyes; Merocyanines, preferably electroneutral merocyanines, more preferably merocyanines in Cyanlimit; perylene; Violanthrones, Isoviolanthrones; Squaric acid dyes; Quinones, coumarins, rhodamines, or porphyrins.
  • metal-containing or metal-free phthalocyanines preferably copper phthalocyanines, silicon phthalocyanines, aluminum phthalocyanines, zinc phthalocyanines, particularly preferably silicon
  • aryl radicals in the general form in the para position may also contain sulfonic acid radicals or alkali metal salts of these substituents (eg -SO 3 H, -SO 3 Na, -SO 3 K).
  • merocyanine dyes are also suitable EP 08168116.5 (Formula IIa p.34 and Formula L2-03 p.37).
  • the merocyanine dye with suitably narrow absorption band.
  • an amount of the marking substance is used which can still be detected with the aid of the respective method for a later detection of the presence of the marking substance.
  • This amount of label may vary over a wide range, for example, depending on the nature of the label or detection method. As a rule, from 50% by weight up to a few ppb, based on the total amount of marker and article to be marked, of the marker is brought into contact with the article to be marked, preferably from 0.01 to 10% by weight.
  • the article to be marked is preferably brought into contact with at least one marker at at least one point on its surface.
  • the location to be marked on the surface is often relatively small in relation to the total surface of the article.
  • the area of the site to be marked is from one square millimeter to one square centimeter.
  • the article to be marked preferably contains paper, for example cardboard or cardboard, metal, glass, ceramic or plastic. Particularly preferably, the article to be marked contains from 1 to 99 wt .-% paper, metal, glass, ceramic or plastic, most preferably from 10 to 99 wt .-%.
  • the object to be marked consists essentially of paper, metal, glass, ceramic and / or plastic.
  • the article to be marked is based on a composite material containing, for example, paper or cardboard and plastic.
  • the object to be marked is based on multilayer plastic films (laminate).
  • the object to be marked contains paper and is a banknote, a security, an admission ticket, a document, a packaging, a label or a document.
  • the object to be marked contains plastic and is a check card, a foil or a packaging.
  • the object to be marked represents a packaging for consumer goods, in particular pharmaceuticals, cosmetics, cleaning agents, foodstuffs or industrial goods, in particular automobile parts.
  • the contacting of the marker with the article to be marked is accomplished by printing the marker or a mixture containing the marker on the article.
  • Inkjet printing inkjet
  • screen printing offset printing
  • flexographic printing thermal printing
  • thermal printing or (electro) photography are preferably used as printing processes.
  • printing inks or inks are used as mixtures containing the marking substance.
  • the formulation of the mixture and / or the application of the marker or the mixture can be done with either aqueous or oil based inks or inks.
  • step b a change in the position of the at least one narrow band made by a solvatochromic, electrochromic, or thermochromic influence.
  • the change in the position of the narrow band by the action of electric and Thermochromism made.
  • a solvatochromic influence on the spectral position of the narrow band can be brought about, for example, by a change in the solvent.
  • Electrochromic influence results from the application and the change of an electric field and a thermochromic influence results from the change of the temperature.
  • a photochromic influence results from the irradiation of electromagnetic radiation.
  • the change of the spectral position is preferably recurring and is modulated with a certain frequency.
  • the modulation frequency is in this case preferably from 0.1 to 10 Hz, in particular from 0.1 to 5 Hz.
  • the irradiation of the object with electromagnetic radiation is preferably carried out with the aid of a narrow-band radiation source.
  • narrow-band radiation sources lasers such as dye lasers, solid-state lasers or laser diodes are used.
  • the narrow-band radiation source preferably has a half-width of 0.01 to 10 nm for the radiation emitted by it, particularly preferably from 0.1 to 5 nm, particularly preferably from 0.1 to 2 nm.
  • the irradiation is carried out with the help of at least two narrow-band radiation sources.
  • At least one of the markers (step a.) Has at least two narrow bands with a half width of 20 cm -1 to 800 cm -1 and these narrow bands are in the UV - and / or visible and / or IR wavelength range of the electromagnetic spectrum and the irradiation (step b.) Is performed by means of at least two narrow-band radiation sources.
  • the determination of the absorption (step d.) Is carried out visually.
  • At least one of the markers (step a.) Has at least two narrow bands with a half-width of 0.5 nm to 10 nm, and these narrow bands are in the UV and / or visible and / or IR wavelength range of the electromagnetic spectrum and the irradiation (step b.) Is performed by means of at least two narrow-band light sources and the determination of the absorption (step d.) Is carried out visually.
  • two light sources are preferably modulated in antiphase (visual lock-in method).
  • the Intensities of the two light beams adjusted so that unlabeled (areas of) objects offer the visual system very similar or substantially the same brightness.
  • the modulation frequency is in this case preferably from 0.1 to 10 Hz, in particular from 0.1 to 5 Hz.
  • the determination of the absorption Is carried out by measuring an absorption spectrum with the aid of a spectrometer.
  • At least one of the markers (step a.) Has at least two narrow bands with a half-value width of 20 cm -1 to 800 cm -1 and these narrow bands are in the UV and / or visible and / or IR wavelength range of the electromagnetic spectrum and the irradiation (step b.) Is performed by means of at least two narrow-band light sources and the determination of the absorption (step d.) Is by measuring an absorption spectrum using a Spectrometer performed.
  • two light sources are preferably modulated in antiphase (electronic lock-in method).
  • the intensities of the two light beams are adjusted so that unmarked (areas of) objects offer the spectrometer very similar or substantially the same intensities.
  • the spectrometer as detection or detection apparatus in marked areas determines an oscillation with the modulation frequency of the light sources.
  • the modulation frequency is in this case preferably from 0.1 to 10 Hz, in particular from 0.1 to 5 Hz.
  • quantities derived from the absorption or the absorption spectrum are used to compare the absorption or the absorption spectrum (step b.).
  • these quantities are intensities or positions of absorption maxima.
  • the comparison Is performed by means of a computer having access to stored data for absorption, absorption spectrum or derived quantities of the authentic object.
  • the method according to the invention can also be carried out using fluorescence measurements, using appropriately markers with narrow fluorescence signals. These markers are preferably selected from the group of the above-mentioned markers.
  • the authentication is carried out with the aid of a ticket, ticket or cash machine.
  • the authentication is performed by means of a portable device.
  • the inventive method for authenticating an article is used in the authentication of consumer goods or industrial goods, in particular securities, documents, packaging.
  • the methods according to the invention for marking for detection and authentication can be carried out with the aid of devices which are known to the person skilled in the art from the prior art and thus can be easily implemented.
  • the combination of narrow band absorption bands, narrow band radiation sources, and the modulation of the radiation source or banding provide an increased safety standard of the tag over known tagging of articles.
  • the basis for the production of the marking ink was the clear lacquer (matt) from Horstmann-Steinberg (ACRYLAC® Matt 57 0080/40, water-based dispersion lacquer).
  • this paint 0.01 wt .-% of the marker at room temperature (21 ° C) were stirred until a homogeneous distribution of the marker was reached.
  • the marker used was a mixture of silicon phthalocaninines:
  • the compounds were used in a 1: 2: 1 (A: B: C) mixture.
  • This marker shows in the marking ink before and after printing a sharp absorption at 666 nm.
  • the solution ethyl acetate shows the mixture at 666 nm a half-width of 265 cm -1 and after printing a half-width of 610 cm -1 .
  • the printing process was carried out with a printing machine from Heidelberger Druckmaschinen type GOT 52 two-color (offset printing).
  • a mark by printing was applied on white SM paper.
  • the concentration The above-mentioned marking substance in the printing ink was reduced to such an extent that, when illuminated with daylight or white artificial light, the marking was located just below the limit of visibility, ie could not be seen with the naked eye.
  • the marked white paper was overprinted with a color image (demo object). This happened with a commercial inkjet printer.
  • This illumination device contains two light sources with different wavelengths. Two laser diodes with wavelengths of 666 nm (absorption maximum of the marker) and 650 nm were used (only weakly absorbed by the marker because of the narrow absorption band).
  • This lighting device has been implemented as a light source in the form of a light pen, with which the mark for the perception can be continuously illuminated with the human eye.
  • Example 1 can be carried out analogously for the case that the detection of the marker pattern is not carried out with the human eye, but with a spectrometer that is used to detect the modulation of an absorption or fluorescence signal.

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Credit Cards Or The Like (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Inspection Of Paper Currency And Valuable Securities (AREA)
  • Printing Methods (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Claims (15)

  1. Procédé de détection de la présence d'inscriptions sur des objets, le procédé comportant les étapes suivantes :
    a. formation d'inscriptions sur l'objet, l'objet sur lequel les inscriptions doivent être apportées étant mis en contact avec au moins une substance d'inscription, le spectre d'absorption de la ou des substances d'inscription en contact avec l'objet présentant au moins une bande étroite dont la largeur à mi-valeur est < 1 500 cm-1 et la ou les bandes étroites étant situées dans la plage des longueurs d'onde UV,
    visibles et/ou IR du spectre électromagnétique,
    b. irradiation de l'objet par un rayonnement électromagnétique comprenant une plage de longueurs d'onde qui recouvre au moins en partie la ou les bandes étroites de la ou des substances d'inscription,
    c. facultativement, pendant l'étape b., exécution d'une modification de la position de la ou des bandes étroites par action solvatochrome, électrochrome, photochrome ou thermochrome et
    d. détermination de l'absorption de l'objet sur une plage de longueurs d'onde qui recouvre au moins en partie la ou les bandes étroites de la ou des substances d'inscription,
    caractérisé en ce que
    l'irradiation de l'objet par un rayonnement électromagnétique est réalisée à l'aide d'au moins deux sources de rayonnement à bande étroite, avec commutation en va-et-vient entre une longueur d'onde à laquelle la substance d'inscription absorbe et une longueur d'onde à laquelle aucune absorption n'a lieu.
  2. Procédé selon la revendication 1, caractérisé en ce que l'étape c. est réalisée.
  3. Procédé selon les revendications 1 ou 2, caractérisé en ce que la détermination de l'absorption est effectuée visuellement.
  4. Procédé selon les revendications 1 ou 2, caractérisé en ce que la détermination de l'absorption est effectuée par mesure du spectre d'absorption à l'aide d'un spectromètre.
  5. Procédé selon les revendications 1 à 4, caractérisé en ce que les substances d'inscription sont sélectionnées parmi les colorants organiques, les chromophores minéraux ou les pigments.
  6. Procédé selon les revendications 1 à 5, caractérisé en ce que les substances d'inscription sont sélectionnées parmi les phtalocyanines contenant des métaux ou ne contenant pas de métaux, les colorants à la cyanine, les mérocyanines, les colorants au pérylène, les violanthrones, les isoviolanthrones, les colorants à l'acide squarique, les quinones, les coumarines, les rhodamines, les porphyrines ou les composés de métaux des terres rares ou des métaux de transition.
  7. Procédé selon les revendications 1 à 6, caractérisé en ce que l'objet sur lequel une inscription doit être apportée est mis en contact avec au moins une substance d'inscription en au moins un emplacement de sa surface.
  8. Procédé selon les revendications 1 à 7, caractérisé en ce que l'objet sur lequel une inscription doit être apportée contient du papier, du métal, du verre, de la céramique ou de la matière synthétique.
  9. Procédé selon la revendication 8, caractérisé en ce que l'objet sur lequel une inscription doit être apportée contient du papier et est un billet de banque, un papier de valeur, une carte d'entrée, un jugement, un emballage, une étiquette ou un document.
  10. Procédé selon la revendication 8, caractérisé en ce que l'objet sur lequel une inscription doit être apportée contient de la matière synthétique et est une carte de banque, un film ou un emballage.
  11. Procédé selon les revendications 9 ou 10, caractérisé en ce que l'objet sur lequel une inscription doit être apportée est un emballage pour produits de consommation ou produits industriels.
  12. Procédé selon les revendications 1 à 11, caractérisé en ce que la mise en contact s'effectue par impression de la substance d'inscription ou d'un mélange contenant la substance d'inscription sur l'objet.
  13. Procédé d'authentification d'un objet, comportant les étapes suivantes :
    a. détection de l'inscription selon les revendications 1 à 12 et
    b. comparaison de l'absorption ou du spectre d'absorption à l'absorption ou au spectre d'absorption qui correspondent à un objet authentifié.
  14. Procédé selon la revendication 13, caractérisé en ce que l'authentification s'effectue à l'aide d'un automate à ticket de voyage, carte d'entrée ou bancaire.
  15. Utilisation du procédé selon les revendications 13 ou 14 pour authentifier des produits de consommation ou des produits industriels.
EP10768457.3A 2009-10-16 2010-10-12 Utilisation de substances de marquage à bandes étroites Revoked EP2488368B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10768457.3A EP2488368B1 (fr) 2009-10-16 2010-10-12 Utilisation de substances de marquage à bandes étroites

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09173310 2009-10-16
EP10768457.3A EP2488368B1 (fr) 2009-10-16 2010-10-12 Utilisation de substances de marquage à bandes étroites
PCT/EP2010/065234 WO2011045294A1 (fr) 2009-10-16 2010-10-12 Substances de marquage à bandes étroites

Publications (2)

Publication Number Publication Date
EP2488368A1 EP2488368A1 (fr) 2012-08-22
EP2488368B1 true EP2488368B1 (fr) 2014-05-14

Family

ID=43431087

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10768457.3A Revoked EP2488368B1 (fr) 2009-10-16 2010-10-12 Utilisation de substances de marquage à bandes étroites

Country Status (5)

Country Link
US (1) US8610893B2 (fr)
EP (1) EP2488368B1 (fr)
JP (1) JP2013507276A (fr)
CN (1) CN102574405B (fr)
WO (1) WO2011045294A1 (fr)

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AT16766U1 (de) * 2018-12-06 2020-08-15 Engel Austria Gmbh Markier- und Detektierverfahren für thermoplastische Halbzeuge

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Publication number Publication date
US8610893B2 (en) 2013-12-17
CN102574405A (zh) 2012-07-11
US20120194801A1 (en) 2012-08-02
JP2013507276A (ja) 2013-03-04
CN102574405B (zh) 2014-11-05
EP2488368A1 (fr) 2012-08-22
WO2011045294A1 (fr) 2011-04-21

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