EP3875285A1 - Fälschungssichere verpackung - Google Patents

Fälschungssichere verpackung Download PDF

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Publication number
EP3875285A1
EP3875285A1 EP20161380.9A EP20161380A EP3875285A1 EP 3875285 A1 EP3875285 A1 EP 3875285A1 EP 20161380 A EP20161380 A EP 20161380A EP 3875285 A1 EP3875285 A1 EP 3875285A1
Authority
EP
European Patent Office
Prior art keywords
laser
packaging
container
image
markable
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Withdrawn
Application number
EP20161380.9A
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English (en)
French (fr)
Inventor
Quentin VAN DEN HOVE D'ERTSENRYCK
Sam Verbrugghe
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.)
Agfa NV
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Agfa NV
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 Agfa NV filed Critical Agfa NV
Priority to EP20161380.9A priority Critical patent/EP3875285A1/de
Publication of EP3875285A1 publication Critical patent/EP3875285A1/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • B42D25/40—Manufacture
    • B42D25/405—Marking
    • B42D25/41—Marking using electromagnetic radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D23/00—Details of bottles or jars not otherwise provided for
    • B65D23/08—Coverings or external coatings
    • B65D23/0842—Sheets or tubes applied around the bottle with or without subsequent folding operations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D41/00—Caps, e.g. crown caps or crown seals, i.e. members having parts arranged for engagement with the external periphery of a neck or wall defining a pouring opening or discharge aperture; Protective cap-like covers for closure members, e.g. decorative covers of metal foil or paper
    • B65D41/62—Secondary protective cap-like outer covers for closure members
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/28—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/28—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating
    • B41M5/286—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using thermochromic compounds or layers containing liquid crystals, microcapsules, bleachable dyes or heat- decomposable compounds, e.g. gas- liberating using compounds undergoing unimolecular fragmentation to obtain colour shift, e.g. bleachable dyes
    • 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/323—Organic colour formers, e.g. leuco dyes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D2203/00—Decoration means, markings, information elements, contents indicators
    • B65D2203/02—Labels
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D2211/00—Anti-theft means

Definitions

  • the present invention relates to the manufacturing of packaging that makes counterfeiting more difficult. More specifically, the packaging guarantees the authenticity of origin of the product contained therein.
  • the containers containing the luxury products for example bottles containing alcoholic drinks or perfume, including the labels and closures, may be collected and re-filled with "fake” alcoholic drink or perfume.
  • WO94/18087 COURVOISIER
  • US2007/0289935 ACAN PACKAGING CAPSULES
  • alkyl means all variants possible for each number of carbon atoms in the alkyl group i.e. methyl, ethyl, for three carbon atoms: n-propyl and isopropyl; for four carbon atoms: n-butyl, isobutyl and tertiary-butyl; for five carbon atoms: n-pentyl, 1,1-dimethyl-propyl, 2,2-dimethyl-propyl and 2-methyl-butyl, etc.
  • a substituted or unsubstituted alkyl group is preferably a C 1 to C 6 -alkyl group.
  • a substituted or unsubstituted alkenyl group is preferably a C 2 to C 6 -alkenyl group.
  • a substituted or unsubstituted alkynyl group is preferably a C 2 to C 6 -alkynyl group.
  • a substituted or unsubstituted aralkyl group is preferably a phenyl or naphthyl group including one, two, three or more C 1 to C 6 -alkyl groups.
  • a substituted or unsubstituted alkaryl group is preferably a C 7 to C 20 -alkyl group including a phenyl group or naphthyl group.
  • a substituted or unsubstituted aryl group is preferably a phenyl group or naphthyl group
  • a substituted or unsubstituted heteroaryl group is preferably a five- or six-membered ring substituted by one, two or three oxygen atoms, nitrogen atoms, sulphur atoms, selenium atoms or combinations thereof.
  • substituted in e.g. substituted alkyl group means that the alkyl group may be substituted by other atoms than the atoms normally present in such a group, i.e. carbon and hydrogen.
  • a substituted alkyl group may include a halogen atom or a thiol group.
  • An unsubstituted alkyl group contains only carbon and hydrogen atoms
  • a substituted alkyl group, a substituted alkenyl group, a substituted alkynyl group, a substituted aralkyl group, a substituted alkaryl group, a substituted aryl and a substituted heteroaryl group are preferably substituted by one or more constituents selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tertiary-butyl, ester, amide, ether, thioether, ketone, aldehyde, sulfoxide, sulfone, sulfonate ester, sulfonamide, -CI, -Br, -I, -OH, -SH, -CN and -NO 2 .
  • the packaged container according to the present invention includes a laser marked image (500) on a packaging (600) wrapped around the container (50).
  • Inspection of the laser marked image (500) may give an indication on whether or not the packaged container has been counterfeited.
  • the packaging may be a foil that is wrapped around the container.
  • the packaging may be transparent or non-transparent, preferably non-transparent.
  • the foil maybe wrapped around the container by pressure, for example a metal foil around the neck of bottle.
  • a metal foil around the neck of bottle is also referred to as a coiffe.
  • a shrink foil may be used.
  • a shrink foil is typically a polymer foil that shrinks tightly over the container when heat is applied.
  • the shrink foil is preferably a shrink sleeve. Such a shrink sleeve may be used for wine bottles, perfume bottles, olive oil bottles but also for plastic containers and pharmaceutical or paramedical products.
  • the laser marked image for example a logo
  • the original image intended to be put on the packaging will correspond with the original image intended to be put on the packaging.
  • Such an image cannot be reproduced by a counterfeiter by printing it on the packaging material before wrapping it around the container. Due to shrinking and/or the unevenness resulting from the wrapping, the pre-printed images will be altered. Such altered images on the wrapped packaging may then be an indication of counterfeiting.
  • a logo has been laser marked on a wrapped packaging (200) including unevenness (220).
  • the logo LOGO is laser marked as intended, despite the unevenness.
  • a straight line (500) is laser marked on a wrapped packaging (200), also including an unevenness (250).
  • the laser marked line (500) is indeed a straight line as intended (see top view in Fig. 4b ).
  • Figure 5 illustrates an indication that the wrapped container has been counterfeited.
  • the logo LOGO has been pre-printed on the packaging (200) before wrapping it around the container.
  • shrinking and/or the occurrence of unevenness will result in an image that does not correspond anymore with the intended image.
  • the image for example the LOGO, may even become unreadable.
  • a pre-printed straight line on the packaging before wrapping it around the container will not be straight anymore after wrapping the packaging around the container.
  • the wrapped packaging (200) includes an unevenness (250) and the image (500) extends over the unevenness. This is schematically illustrated in Figure 4 .
  • the wrapped packaging (200) includes an area (230) that is not capable of being exposed to the laser (300) between a first (220) and a second (240) area that is capable of being exposed to the laser (300) and the laser marked image (500) extends over both the first (220) and the second area (240) of the packaging.
  • This embodiment is schematically illustrated in Figures 2 and 3 .
  • a simple visual inspection of the areas that are not capable of being laser marked (230) will reveal that indeed those areas will not contain a part of the image.
  • the image would be pre-printed on the packaging before wrapping it around the container then also those areas (230) that are not capable of being laser marked will also contain a part of the image.
  • the image will then also be altered compared to the original image. This means that a simple visual inspection will reveal a counterfeited packaged container.
  • the container is a bottle (50).
  • a preferred packaging for such a bottle for example a bottle of champagne, is a coiffe (600).
  • the container also comprises a laser markable label (700) at least partially overlapping the wrapped packaging (600) and wherein a second image (550) is laser marked with a laser, the second image extending over both the label and the wrapped packaging (see Figure 1 ).
  • the second image When the container is opened, the second image will be destroyed.
  • the destroyed image may also be an indication of counterfeiting.
  • the second image (550) is preferably an image that is difficult or even impossible to reproduce by pre-printing a first part of that image on the wrapped packaging (600) and a second part of that image on the label (700).
  • the first (500) and the second (550) image may be laser marked with the same laser or with different lasers, for example having different emission wavelengths.
  • the latter embodiment makes it even more difficult for a counterfeiter to reproduce the packaged container.
  • the laser markable packaging may be laser marked by exposing it to a laser, preferably an Infrared (IR) laser, more preferably a Near Infrared (NIR) Laser.
  • a laser preferably an Infrared (IR) laser, more preferably a Near Infrared (NIR) Laser.
  • the laser markable packaging may include a laser markable packaging material.
  • the laser markable packaging may be a resin based material comprising laser markable pigments dispersed therein, as for example disclosed in WO2018/095834 (Merck ).
  • the laser markable packaging is a packaging material including a laser markable coating.
  • a laser markable composition is applied on at least one surface of a packaging material thereby forming the laser markable coating on the packaging material.
  • the laser markable coating may be provided on the whole surface of the packaging material or on a part of the surface.
  • the laser markable composition may be applied onto the packaging material by co-extrusion or any conventional coating technique, such as dip coating, knife coating, extrusion coating, spin coating, spray coating, slide hopper coating and curtain coating.
  • the laser markable composition may also be applied onto the packaging material by any printing method such as intaglio printing, screen printing, flexographic printing, offset printing, inkjet printing, rotogravure printing, etc.
  • the laser markable coating may include two, three or more laser markable layers, each layer capable of forming a different colour.
  • Such laser markable coatings capable of forming multicolour images are disclosed in for example EP-A 2722367 (Agfa Gevaert) and WO2013/068729 (Datalase).
  • a protective coating maybe provided on top of the laser markable coating.
  • the protective coating may provide the image with a certain scratch resistance and can also provide a glossy finish to the image.
  • the protective coating may also comprise UV absorbers to improve the daylight stability of the laser marked images.
  • the protective coating is preferably substantially transparent to ensure efficient laser marking through the protective coating.
  • the packaging material may be any material but is preferably a metal or a resin based foil.
  • a preferred metal foil is an aluminium or tin based foil, more preferably an aluminium based foil.
  • a coiffe referred to above is typically an aluminium based foil, for example an aluminium-polyethylene composite foil.
  • a resin based foil is defined as a foil having a continuous phase of a synthetic, a semi-synthetic or natural polymeric material.
  • the thickness of the foil is preferably less than 500 ⁇ m, more preferably less than 250 ⁇ m, most preferably less than 100 ⁇ m.
  • Synthetic resins are defined as resins requiring at least one polymerization step in the manufacturing of the resin.
  • Typical examples are poly(olefines) such as high density polyethylene (PE), low density PE, polypropylene (PP), polyesters, poly(amides), poly(urethanes), poly(acetals), poly(ethers), or a combination thereof.
  • Semi-synthetic resins are defined as resins prepared from natural polymers, such as cellulose, by converting into the final resin by at least one synthetic chemical modification step, such as esterification or alkylation.
  • Typical examples are cellulose acetate butyrate (CAB), cellulose triacetate, nitrocellulose, carboxymethyl cellulose, or phthaloyl gelatin.
  • Natural resin are defined as resins extracted from natural resources and which are not further modified by synthetic chemical steps. Typical examples are dextranes, pullulan, etc.
  • Synthetic resins and semi-synthetic resins are particularly preferred, synthetic resins being the most preferred.
  • Poly(esters), poly(amides) and poly(olefins) are particularly preferred, pol(olefins) being the most preferred.
  • the resin based article is a thermoplastic polymeric film or foil.
  • thermoplastic polymers include polyolefines such as polyethylene (PE), polypropylene (PP), polyesters such as polyethylene terephthalate (PET), polyethylene 2,5-difurandicarboxylate (PEF) and polyethylene naphthenate (PEN), polylactic acid (PLA), polyacrylonitrile (PAN), polyamides (PA), polyurethanes (PU), polyacetals, such as polyvinylbutyral, polymethyl methacrylate (PMMA), polyimide (PI), polystyrene (PS), polycarbonate (PC), acrylonitrile-butadiene-styrene (ABS), polyvinylchloride (PVC), and copolymers thereof.
  • PE polyethylene
  • PP polypropylene
  • PET polyethylene terephthalate
  • PET polyethylene 2,5-difurandicarboxylate
  • PEN polyethylene naphthenate
  • PDA polylactic acid
  • PAN polyacrylonitrile
  • PA polyamide
  • thermoplastic polymers are polyethylene (PE), polypropylene (PP), polyethylene terephthalate (PET) and polyethylene 2,5-furandicarboxylate (PEF).
  • PEF may be produced using a biobased furandicarboxylic acid (FDCA)
  • FDCA biobased furandicarboxylic acid
  • the carbon footpring of its manufacturing process is much smaller compared to for example the production of PET.
  • its barrier properties for example for O 2 and CO 2 , may be better.
  • shrink foil The most commonly used shrink foil includes polyolefin. It is available in a variety of thicknesses, clarities, strengths and shrink ratios. Other shrink foils include PVC, Polyethylene, Polypropylene, and several other compositions.
  • the laser markable label preferably includes a laser markable coating as described above for the laser markable packaging.
  • the laser markable coating for the packaging and the label may be the same or different.
  • the laser markable coating of the label includes a different leuco dye compared to the coating of the laser markable packaging. This means that a laser marked image on the wrapped packaging will have a different colour compared to the laser marked image on the label.
  • a laser marked image (550) is provided that extends over both the label and the wrapped packaging, the part of the image on the label and the part of the image on the wrapped packaging will have a different colour. This will make it even more difficult for a counterfeiter.
  • laser markable coatings of the wrapped packaging and the label preferably includes different optothermal converting agents adapted for both lasers.
  • the method of manufacturing a packaged container as described above according to the present invention comprises the step of laser marking the first image (500) and/or second image (550) with a laser (300).
  • the method includes the step of wrapping the packaging around the container before the laser marking step.
  • the method includes the step of providing the laser markable label overlapping the wrapped packaging before the laser marking step.
  • any laser may be used in the laser marking step.
  • Preferred lasers are ultraviolet (UV) and infrared (IR) lasers, infrared laser being particularly preferred.
  • the infrared laser may be a continuous wave or a pulsed laser.
  • a CO 2 laser For example a CO 2 laser, a continuous wave, high power infrared laser having an emission wavelength of typically 10600 nm (10.6 micrometer) may be used.
  • CO 2 lasers are widely available and cheap.
  • a disadvantage however of such a CO 2 laser is the rather long emission wavelength, limiting the resolution of the laser marked information.
  • NIR near infrared
  • a particularly preferred NIR laser is an optical pumped semiconductor laser.
  • Optically pumped semiconductor lasers have the advantage of unique wavelength flexibility, different from any other solid-state based laser.
  • the output wavelength can be set anywhere between about 920 nm and about 1150 nm. This allows a perfect match between the laser emission wavelength and the absorption maximum of an optothermal converting agent present in the laser markable layer.
  • a preferred pulsed laser is a solid state Q-switched laser.
  • Q-switching is a technique by which a laser can be made to produce a pulsed output beam. The technique allows the production of light pulses with extremely high peak power, much higher than would be produced by the same laser if it were operating in a continuous wave (constant output) mode, Q-switching leads to much lower pulse repetition rates, much higher pulse energies, and much longer pulse durations.
  • One or multiple lasers may be used to laser mark.
  • One or more lasers may be used. Also, a so-called laser bar, for example a LED bar, may be used to laser mark.
  • Laser marking is carried out with an infrared laser.
  • the infrared laser may be a continuous wave or a pulsed laser.
  • Laser marking may also be carried out using a so-called Spatial Light Modulator (SLM) as disclosed in WO2012/044400 (Vardex Laser Solutions).
  • SLM Spatial Light Modulator
  • the image may contain decorative features, company logo's, trademarks, photographs, drawings and/or information.
  • the information may be human readable, such as text, or it may be machine readable, such as a bar code, or a combination of both.
  • machine readable code there is no restriction on the type of machine readable code or the information it contains. It may be a simple bar code, but it may also be a so-called 2D code. Preferred 2D codes include a QR code, a datamatrix code, a cool-data-matrix code, an aztec code, an upcode, a trillcode, a quickmark code, a shot code, a mcode, and a beetagg.
  • the image include a digital fingerprint code as disclosed in EP3120293 (AGFA) and/or a Digimarc® barcode.
  • AGFA digital fingerprint code
  • Digimarc® barcode Both machine-readable codes, generally imperceptible to the human eye, enables identification of the packaged products with for example phones, barcode scanners, cameras, fixed-mount barcode readers and other computer interfaces.
  • the image preferably includes a 2D barcode as disclosed in EP-A 3252680 (Agfa).
  • a 2D barcode as disclosed in EP-A 3252680 (Agfa).
  • the image may also include known security features such as guilloches or microprints.
  • the information present in a machine readable code may be the required information or it may be a link for retrieving the information from a source, such as a database or the internet.
  • the image may also contain a communication for enhancing the customer engagement.
  • An image for enhancing customer engagement may also contain a machine readable code, such as a QR-code, which after scanning by the smartphone of a customer leads to a website of the merchandise article manufacturer for enhancing the customer experience.
  • a laser markable composition typically comprises a colour forming agent.
  • the colour forming agent is capable of forming a colour upon exposure with a laser.
  • the laser markable composition includes an optothermal converting agent that is capable of converting radiation energy in to heat.
  • the laser markable compositions may be aqueous compositions or non-aqueous compositions. Both the aqueous and non-aqueous compositions may be radiation curable, preferably UV curable.
  • Such radiation curable laser markable composition typically include one or more polymerizable compounds and one or more photo-initiators.
  • a curing step is carried out by exposing the applied composition to radiation, preferably UV radiation.
  • Non-aqueous laser markable compositions are disclosed in for example EP-A 3083261 (Agfa Gevaert).
  • Preferred radiation curable non-aqueous laser markable compostion are disclosed in for example EP-A 19202712.6 (Agfa Gevaert filed on 11-10-2019).
  • a preferred aqueous based composition includes encapsulated leuco dyes.
  • leuco dyes are disclosed in for example EP-A 3297837 , EP-A 3470134 and EP-A 3470135 , all from Agfa Gevaert.
  • Preferred radiation curable aqueous composition are disclosed in EP-A 18196206.9 and EP-A 18196211.9 (both from Agfa Gevaert and filed on 24-09-2018).
  • the laser markable composition is preferably a flexographic or inkjet ink.
  • additives may be added to the composition, such as surfactants, wetting/levelling agents, rheology modifiers, adhesion promoting compounds, biocides or antioxidants may be added to the laser markable composition.
  • the laser markable composition comprises a colour forming agent, which is capable of forming a colour upon laser marking.
  • a transition metal oxide such as molybdenum trioxide, has been disclosed in WO2008/075101 (SILTECH).
  • These colour forming agents are capable of forming a black colour upon laser marking.
  • Diacetylene compounds such as disclosed in WO2013/014436 (DATALASE) are capable of forming multiple colours.
  • Preferred colour formers are leuco dyes, as described below.
  • a leuco dye is preferably used in combination with a developing agent.
  • a combination of different colour forming agents may be used, for example to produce different colours.
  • WO2013/068729 (DATALASE)
  • a combination of a diacetylene compound and a leuco dye is used to produce a full colour image upon exposure to UV and IR radiation.
  • a leuco dye is a substantially colourless compound, which may form a coloured dye upon an inter- or intra-molecular reaction.
  • the inter- or intra-molecular reaction may be triggered by heat, preferably heat formed during exposure with an IR laser.
  • leuco dyes are disclosed in WO2015/165854 (Agfa Gevaert), paragraph [069] to [093].
  • the laser markable composition may comprise more than one leuco dye. Using two, three or more leuco dyes may be necessary to realize a particular colour. Also, it has been observed that more stable dispersions may be obtained when two, three or more leuco dyes are used.
  • the amount of leuco dye in the laser markable layer is preferably in the range from 0.05 to 2 g/m 2 , more preferably in the range from 0.1 to 1 g/m 2 .
  • the radiation curable laser markable composition preferably comprises a developing agent.
  • a developing agent is capable of reacting with a colourless leuco dye resulting in the formation of a coloured dye upon laser marking.
  • a compound is released that may react with a leuco dye thereby forming a coloured dye.
  • Thermal acid generators are for example widely used in conventional photoresist material. For more information see for example " Encyclopaedia of polymer science", 4th edition, Wiley or “ Industrial Photoinitiators, A Technical Guide", CRC Press 2010 .
  • Preferred classes of photo- and thermal acid generators are iodonium salts, sulfonium salts, ferrocenium salts, sulfonyl oximes, halomethyl triazines, halomethylarylsulfone, ⁇ -haloacetophenones, sulfonate esters, t-butyl esters, allyl substituted phenols, t-butyl carbonates, sulfate esters, phosphate esters and phosphonate esters.
  • Particularly preferred developing agents have a structure according to Formula (I) wherein
  • Such developing agents according to Formula I and their preparation are disclosed in WO2015/091688 .
  • An optothermal converting agent generates heat upon absorption of radiation.
  • the optothermal converting agent preferably generates heat upon absorption of infrared (IR) radiation, more preferably near infrared (NIR) radiation.
  • IR infrared
  • NIR near infrared
  • Near infrared radiation has a wavelength between 750 and 2500 nm.
  • Optothermal converting agents may be an infrared radiation absorbing dye but is preferably an infrared radiation absorbing pigment, or a combination thereof.
  • a preferred inorganic infrared absorber is a copper salt as disclosed in WO2005/068207 (DATALASE).
  • Another preferred inorganic infrared absorber is a non-stoichiometric metal salt, such as reduced indium tin oxide as disclosed in WO2007/141522 (DATALASE).
  • Particular preferred inorganic infrared absorbers are tungsten oxide or tungstate as disclosed in WO2009/059900 (DATALASE) and WO2015/015200 (DATALASE).
  • a lower absorption in the visible region while having a sufficient absorption in the near infrared region is an advantage of these tungsten oxide or tungstate.
  • IR pigment is carbon black, such as acetylene black, channel black, furnace black, lamp black, and thermal black.
  • the amount of carbon black in the laser markable layer is preferably less than 0.1 g/m2, more preferably less than 0.01 g/m2, most preferably less than 0.005 g/m2.
  • IR dyes Infrared absorbing dyes
  • IR pigments An advantage of Infrared absorbing dyes (IR dyes) compared to IR pigments is their narrow absorption spectrum resulting in less absorption in the visible region. This may be of importance for the processing of transparent resin based articles where optical appearance is of importance.
  • a narrow absorption band is also mandatory for multicolour laser marking using multiple laser each having a different emission wavelength, as disclosed in for example EP-A 3297838 .
  • a narrow absorption band of the IR dye necessitates a good match between absorption maximum of the IR dye and the emission wavelength of the IR laser used to laser mark.
  • these differ too much for example more than 150 nm, it is not possible anymore to obtain laser marked images having a sufficient density.
  • an IR dye having an absorption maximum that does not correspond to the emission wavelength of readily available IR lasers for example around 950 nm, it becomes even more difficult to counterfeit the packaging.
  • IR dye Any IR dye may be used, for example the IR dyes disclosed in "Near-Infrared Dyes for High Technology Applications” (ISBN 978-0-7923-5101-6).
  • Preferred IR dyes are polymethine dyes due to their low absorption in the visible region and their selectivity, i.e. narrow absorption peak in the infrared region.
  • Particular preferred polymethine IR dyes are cyanine IR dyes.
  • Preferred IR dyes having an absorption maximum of more than 1100 nm are those disclosed in EP-A 2722367 , paragraphs [0044] to [0083] and WO2015/165854 , paragraphs [0040] to [0051].
  • IR dyes having an absorption maximum between 1000 nm and 1100 nm are preferably selected from the group consisting of quinoline dyes, indolenine dyes, especially a benzo[cd]indoline dye.
  • a particularly preferred IR dye is 5-[2,5-bis[2-[1-(1-methylbutyl)-benz[cd]indol-2(1H)-ylidene]ethylidene]-cyclopentylidene]-1 -butyl-3-(2-methoxy-1 -methylethyl)- 2,4,6(1 H,3H,5H)-pyrimidinetrione (CASRN 223717-84-8) represented by the Formula IR-1, or the IR dye represented by Formula IR-2:
  • Both IR dyes IR-1 and IR-2 have an absorption maximum ⁇ max around 1052 nm making them very suitable for a Nd-YAG laser having an emission wavelength of 1064 nm.
  • NIR absorbing compounds are those disclosed in WO2019/007833 , paragraph [0034] to [0046]. It has been observed that these NIR absorbing compounds are more stable compared to for example those disclosed in WO2015/165854 .
  • a combination of different optothermal converting agents may also be used.
  • the amount of optothermal converting agent is preferably at least 10 -10 g/m 2 , more preferably between 0.0001 and 0.5 g/m 2 , most preferably between 0.0005 and 0.1 g/m 2 .
  • the laser markable composition including the color forming agent and/or the composition including the optothermal converting agent may be radiation curable compositions, preferably UV curable compositions.
  • Such radiation curable compositions comprise a polymerizable compound.
  • the polymerizable compounds may be monomers, oligomers or prepolymers.
  • the polymerizable compounds may be free radical polymerizable compounds or cationic polymerizable compounds.
  • Cationic polymerization is superior in effectiveness due to lack of inhibition of the polymerization by oxygen, however it is expensive and slow, especially under conditions of high relative humidity. If cationic polymerization is used, it is preferred to use an epoxy compound together with an oxetane compound to increase the rate of polymerization.
  • Preferred monomers and oligomers are those listed in paragraphs [0103] to [0126] of EP-A 1911814 .
  • Preferred free radical polymerizable compounds include at least one acrylate or methacrylate group as polymerizable group, referred to herein as (meth)acrylate monomers, oligomers or prepolymers. Due to their higher reactivity, particularly preferred polymerizable compounds are acrylate monomers, oligomers or prepolymers.
  • N-vinylamides such as N-vinylcaprolactam and acryloylmorpholine.
  • Particular preferred (meth)acrylate monomers, oligomers or prepolymers are selected from the group consisting of tricyclodecanedimethanol diacrylate (TCDDMDA), isobornyl acrylate (IBOA), dipropylene glycol diacrylate (DPGDA), ethoxylated [4] bisphenol diacrylate and urethane acrylate.
  • TCDDMDA tricyclodecanedimethanol diacrylate
  • IBOA isobornyl acrylate
  • DPGDA dipropylene glycol diacrylate
  • ethoxylated [4] bisphenol diacrylate urethane acrylate
  • the radiation curable laser markable composition preferably contains a photoinitiator.
  • the initiator typically initiates the polymerization reaction.
  • the photo-initiator may be a Norrish type I initiator, a Norrish type II initiator or a photo-acid generator, but is preferably a Norrish type I initiator, a Norrish type II initiator or a combination thereof.
  • a preferred Norrish type I-initiator is selected from the group consisting of benzoinethers, benzil ketals, ⁇ , ⁇ -dialkoxyacetophenones, ⁇ -hydroxyalkylphenones, ⁇ -aminoalkylphenones, acylphosphine oxides, acylphosphine sulphides, ⁇ -haloketones, ⁇ -halosulfones and ⁇ -halophenylglyoxalates.
  • a preferred Norrish type II-initiator is selected from the group consisting of benzophenones, thioxanthones, 1,2-diketones and anthraquinones.
  • Suitable photo-initiators are disclosed in CRIVELLO, J.V., et al. VOLUME III: Photoinitiators for Free Radical Cationic & Anionic Photopolymerization. 2nd edition. Edited by BRADLEY, G.. London,UK: John Wiley and Sons Ltd, 1998. p.287-294 .
  • a preferred amount of photoinitiator is 0.3 - 20 wt% of the total weight of the radiation curable composition, more preferably 1 - 15 wt% of the total weight of the radiation curable composition.
  • the radiation curable composition may additionally contain co-initiators.
  • a preferred co-initiator is selected from the group consisting of an aliphatic amine, an aromatic amine and a thiol. Tertiary amines, heterocyclic thiols and 4-dialkylamino-benzoic acid are particularly preferred as co-initiator.
  • the most preferred co-initiators are aminobenzoates for reason of shelf-life stability of the radiation curable composition.
  • a preferred amount of photoinitiator is 0.3 - 20 wt% of the total weight of the radiation curable composition, more preferably 1 - 15 wt% of the total weight of the radiation curable composition.
  • the amount of co-initiator or co-initiators is preferably from 0.1 to 20.0 wt%, more preferably from 1.0 to 10.0 wt%, based in each case on the total weight of the radiation curable composition.
  • the radiation curable laser markable composition may contain a polymerization inhibitor.
  • Suitable polymerization inhibitors include phenol type antioxidants, hindered amine light stabilizers, phosphor type antioxidants, hydroquinone monomethyl ether commonly used in (meth)acrylate monomers, and hydroquinone, t-butylcatechol, pyrogallol may also be used.
  • Suitable commercial inhibitors are, for example, SumilizerTM GA-80, SumilizerTM GM and SumilizerTM GS produced by Sumitomo Chemical Co. Ltd.; GenoradTM 16, GenoradTM 18 and GenoradTM 20 from Rahn AG; IrgastabTM UV10 and IrgastabTM UV22, TinuvinTM 460 and CGS20 from Ciba Specialty Chemicals; FloorstabTM UV range (UV-1, UV-2, UV-5 and UV-8) from Kromachem Ltd, AdditolTM S range (S100, S110, S120 and S130) from Cytec Surface Specialties.
  • the amount capable of preventing polymerization is determined prior to blending.
  • the amount of a polymerization inhibitor is preferably lower than 2 wt% of the total radiation curable laser markable composition.
  • the radiation curable laser markable composition may contain at least one surfactant.
  • the surfactant(s) can be anionic, cationic, non-ionic, or zwitter-ionic and are usually added in a total quantity less than 5 wt% based on the total weight of the inkjet ink and particularly in a total less than 2 wt% based on the total weight of the composition.
  • the radiation curable laser markable composition preferably have a surface tension between 18.0 and 45.0 mN/m at 25°C, more preferably between a surface tension between 21.0 and 39.0 mN/m at 25°C.
  • Preferred surfactants are selected from fluoro surfactants (such as fluorinated hydrocarbons) and/or silicone surfactants.
  • the silicone surfactants are preferably siloxanes and can be alkoxylated, polyester modified, polyether modified, polyether modified hydroxy functional, amine modified, epoxy modified and other modifications or combinations thereof.
  • Preferred siloxanes are polymeric, for example polydimethylsiloxanes.
  • Preferred commercial silicone surfactants include BYKTM 333 and BYKTM UV3510 from BYK Chemie.
  • Silicone surfactants are often preferred in radiation curable laser markable composition, especially the reactive silicone surfactants, which are able to be polymerized together with the polymerizable compounds during the curing step.
  • Examples of useful commercial silicone surfactants are those supplied by BYK CHEMIE GMBH (including BykTM-302, 307, 310, 331, 333, 341, 345, 346, 347, 348, UV3500, UV3510 and UV3530), those supplied by TEGO CHEMIE SERVICE (including Tego RadTM 2100, 2200N, 2250, 2300, 2500, 2600 and 2700), EbecrylTM 1360 a polysilixone hexaacrylate from CYTEC INDUSTRIES BV and EfkaTM-3000 series (including EfkaTM-3232 and EfkaTM-3883) from EFKA CHEMICALS B.V..
  • the laser markable composition preferably comprises at least 1 wt% of an inorganic filler, relative to the total weight of the composition.
  • inorganic fillers examples include calciumcarbonate, clays, alumina trihydrate, talc, mica, and calcium sulphate.
  • an inorganic nanofiller is used to obtain optimal transparency of the laser markable composition.
  • a preferred nanofiller is nanosilica.
  • Nanosilica as referred to herein consist of amorphous silicon dioxide particles having a nano-particle size.
  • the particle size of the nanosilica is preferably in the range from 5 to 250 nm, more preferably in the range from 7.5 to 100 nm, most preferably in the range from 10 to 50 nm.
  • dispersions of nanosilica in acrylate monomers are used.
  • Such commercially available dispersions are for example the Nanocryl® nanosilica dispersions available from Evonik.
  • the amount of the inorganic filler is preferably in the range from 1 to 15 wt%, more preferably in the range from 2 to 10 wt%, most preferably in the range from 2.5 and 7.5 wt%, all relative to the total weight of the composition.
  • the amount of the inorganic filler is preferably in the range from 0.1 to 1.5 g/m2, more preferably in the range from 0.2 to 1 g/m2, most preferably in the range from 0.25 to 0.75 g/m2.
  • the laser markable composition may comprise a white pigment. With such a composition, a white laser markable layer may be formed.
  • the white background typically results in an enhanced contrast of the laser marked image. This may be particularly useful for laser marking barcodes or QR codes.
  • Such a white background may also be realised by applying a white primer before applying a transparent laser markable composition on top of the white primer.
  • the pigments described below may be used both in the laser markable composition or the primer.
  • the white pigment may be an inorganic or an organic pigment.
  • the white pigment may be selected from titanium oxide, barium sulfate, silicon oxide, aluminium oxide, magnesium oxide, calcium carbonate, kaolin, or talc.
  • a preferred white pigment is titanium oxide.
  • Titanium oxide occurs in the crystalline forms of anatase type, rutile type and brookite type.
  • the anatase type has a relatively low density and is easily ground into fine particles, while the rutile type has a relatively high refractive index, exhibiting a high covering power. Either one of these is usable in this invention. It is preferred to make the most possible use of characteristics and to make selections according to the use thereof.
  • the use of the anatase type having a low density and a small particle size can achieve superior dispersion stability, ink storage stability and ejectability. At least two different crystalline forms may be used in combination.
  • the combined use of the anatase type and the rutile type which exhibits a high colouring power can reduce the total amount of titanium oxide, leading to improved storage stability and ejection performance of ink.
  • an aqueous treatment or a gas phase treatment is applied, and an alumina-silica treating agent is usually employed.
  • an alumina-silica treating agent is usually employed for surface treatment of the titanium oxide.
  • Untreated-, alumina treated- or alumina-silica treated-titanium oxide are employable.
  • the volume average particle size of the white pigment is preferably between 0.03 ⁇ m and 0.8 ⁇ m, more preferably between 0.15 ⁇ m and 0.5 ⁇ m. When the volume average particle size of the white pigment is within these preferred ranges, the reflection of light is sufficient to obtain a sufficiently dense white colour.
  • the volume average particle size may be measured by a laser diffraction/scattering type particle size distribution analyzer.

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  • Toxicology (AREA)
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  • Heat Sensitive Colour Forming Recording (AREA)
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Cited By (3)

* Cited by examiner, † Cited by third party
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WO2022070756A1 (en) 2020-09-29 2022-04-07 Ricoh Company, Ltd. Container and containing body
CN116362773A (zh) * 2023-05-31 2023-06-30 酒仙网络科技股份有限公司 一种基于数据分析的红酒智能防伪系统
WO2024223261A1 (de) * 2023-04-28 2024-10-31 Krones Ag Kunststoffbehältnis aus einheitlichem material und verfahren zu dessen herstellung

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022070756A1 (en) 2020-09-29 2022-04-07 Ricoh Company, Ltd. Container and containing body
EP4222069A4 (de) * 2020-09-29 2024-03-13 Ricoh Company, Ltd. Behälter und aufnahmekörper
WO2024223261A1 (de) * 2023-04-28 2024-10-31 Krones Ag Kunststoffbehältnis aus einheitlichem material und verfahren zu dessen herstellung
CN116362773A (zh) * 2023-05-31 2023-06-30 酒仙网络科技股份有限公司 一种基于数据分析的红酒智能防伪系统
CN116362773B (zh) * 2023-05-31 2023-07-28 酒仙网络科技股份有限公司 一种基于数据分析的红酒智能防伪系统

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