• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    In a sensor ink comprising at least one fluorophore, a polymeric support matrix and at least one organic solvent is a carrier matrix as a organi cal system or a homo- or co-polymer selected from the group polystyrenes, Polysul fone, polyetherimides, polyethersulfones, polyvinyl chloride (PVC ), Polyphenylene oxide (PPO), poly sulfone derivatives, polyethylene terephthalate, biobased polymers, polylactic acid, cellulose esters and cellulose ethers having a molecular weight between 80,000 and 300,000, preferably between 100,000 and 240,000, and the fluororephor is in an amount of 1.5% by weight 7 wt .-% based on the polymer concentration, wherein the carrier matrix and the Fluorephor with the organic solvent form a viscosity of between 4 and 200 mPa · s having solution, and a method for producing a fluorescence sensor and sensor.
    公开号:AT520591A1
    申请号:T422/2017
    申请日:2017-10-30
    公开日:2019-05-15
    发明作者:Iris Maria Ribitsch Dr；Claudia Pekari-Krottmaier Mag；Zehetner Gerhard；Johannes Krottmaier Dr
    申请人:Technische Farben Ges B R；
    IPC主号:
    专利说明:

    The present invention relates to a sensor ink comprising at least one fluorophore, a polymeric carrier matrix and at least one organic solvent and a method for producing a fluorescence sensor using the sensor ink and a sensor produced in this way.
    Fluorescence or luminescence sensors, which are used to measure gas concentrations in the interior of, for example, food packaging or pharmaceuticals, have been known for some time and are used in particular to determine whether, for example, the packaging is tight or whether the products contained in the packaging already spoiled and can no longer be used. Since at the same time the number of pre-packaged, especially gas-tight packed products that go on sale, steadily rising and, for example, in the food sector sausage, cheese or meat are almost exclusively already sold in packaged form, it is both for the manufacturer and for the Consumers of increasing importance to be able to immediately determine whether the packaged products are still edible, whether the packaging is tight or the hygiene requirements are met.
    Recently, methods have been developed with which sensors can be applied to the inside of packages, which sensors can subsequently be read out without contact or by contacting the film with the read-out detector such that depending on the emitted or unexposed beams Beams can be immediately recognized whether the products contained inside the package are in order, for example, whether the oxygen content inside the package is too high, indicating a leaking packaging, or the like.
    Such sensors, which usually consist of luminescent or fluorescent dyes contained in a polymer matrix, have been applied to the inside of the film by means of special printing methods, such as screen printing or sputtering, whereby sensor dots or patterns on the inside of the package were obtained. The sensors have a relatively large thickness of about 40 pm and in addition to the excessive consumption of polymer and fluorescent or luminescent dye and a long time to dry, so that these sensors in a continuous process, especially in mass production, hardly for Can use, since the slowness of the manufacturing process and in particular the large or thick sensor points formed have proven to be disadvantageous.
    There is therefore still a need for the formation of a sensor or a sensor ink, with which it is possible to form extremely thin sensor dots on plastic films, which thin sensor points, however, sufficiently high concentrations of fluorescence or. On the other hand, which sensor points can be dried so quickly that they are already in a dried state when leaving the printer luminecent dye in order to be able to read them out without doubt and safely. Finally, a production method of such sensors must be able to be implemented on common mass media in order to be able to provide a sufficient number of sensors for bulk goods.
    The invention therefore aims to provide such a sensor ink satisfying the above requirements, as well as a method of manufacturing a fluorescence sensor using such a sensor ink, and a sensor formed using such a sensor ink.
    To achieve the object, the sensor ink according to the invention is essentially characterized in that the carrier matrix is a silicon-organic system or a homo- or co-polymer selected from the group polystyrenes, polysulfones, polyetherimides, polyethersulfone, polyvinyl chloride (PVC), polyphenylene oxide ( PPO), polysulfone derivatives, polyethylene terephthalate, biobased polymers such as Polylactic acid, cellulose esters and cellulose ethers having a molecular weight of between 80,000 and 300,000, preferably between 100,000 and 240,000, the fluorophore is present in an amount of from 1.0% to 7% by weight, based on the polymer concentration, and in that the carrier matrix and the fluorophore with the organic solvent form a solution having a viscosity between 4 and 200 mPa's. By using as the carrier material for the sensor ink, a silicon-organic system or a homo- or copolymer selected from the group polystyrenes, polysulfones, polyetherimides, polyethersulfones, polyvinyl chloride (PVC), polyphenylene oxide (PPO), polysulfone derivatives, polyolefins, polyethylene terephthalate, biobased polymers, polylactic acid, Cellulose esters and cellulose ethers having a molecular weight of between 80,000 and 300,000, preferably between 100,000 and 240,000, it is possible to provide a basis for the trained from the sensor ink sensor which is deformable after application to, for example, a plastic film and even with excessive movement the film, for example a packaging material, to which such a sensor point is applied, does not break or detach from the packaging material. A formed from this polymer or copolymer sensor is flexible, elastic and adheres well to a variety of plastic surfaces. However, the sensor can also be used on non-deformable or slightly deformable, transparent or semi-transparent materials such as e.g. Glass containers or relatively rigid plastic containers are used.
    Furthermore, by having the fluorophore present in the polymeric matrix in the amount of 1.5% to 7% by weight, based on the polymer concentration, it is possible to incorporate sufficient amounts of fluorophore into the sensor ink to produce a sensor This ink to be able to measure a reproducible signal, which is not too weak and in particular does not allow erroneous interpretations. In this case, the polymer concentration is substantially chosen so that a fluorescence signal received by a detector is greater by at least a factor of 5 than the background signal. When the concentration of
    Fluorophore in the sensor ink drops below 1.0% by weight, a sufficiently strong fluorescence or luminescence signal of the sensor can no longer be guaranteed, and if the content rises above 7% by weight, based on the polymer concentration, it can not be prevented that an aggregation or accumulation of individual sensor molecules and a clumping thereof in the interior of a zusammengeallten from the sensor ink according to the invention sensor, which can lead to self-extinction of a fluorescence or luminescence signal, whereby measurement results can be inaccurate and especially not representative ,
    By further containing, in addition to the carrier matrix and the fluorophore, an organic solvent, with which the viscosity of the sensor ink is adjusted to a value between 4 and 200 mPa's, it is possible to produce a printable ink, which can be used in particular in mass printing processes in which it It is necessary that the used inks are thin and, especially after application, dry extremely quickly, the solvent must be selected so that it dries residue-free and allows sensors with extremely small layer thicknesses of a few pm, such as 1 - 10 pm.
    The term sensor ink as used in the present application includes any solution consisting of a polymer, a fluorophore and a low boiling solvent, regardless of the fact whether this solution is a colored or non-colored solution. The only criterion is that the fluorophore molecules contained in this sensor ink can be excited to emit a fluorescent or luminescent light and are present in molecular solution in the sensor ink.
    By, as corresponds to a development of the invention, the sensor ink is formed so that the fluorophore contained therein is selected from the group of metal porphyrins, Phenanthrolinkomplexe, such as diphenylphenantroline, ruthenium (II) complexes, fluorescein derivatives, coumarin derivatives and Phenylmethanfarbstoffe. The fact that the fluorophore is selected from the abovementioned group or from derivatives of this group, in particular various derivatives of metalloporphyrins, makes it possible to provide a sensor ink in which even large concentrations of about 3 to 7% of the fluorophore are dissolved Form present in the polymer matrix and which fluorophore in particular is not prone to form aggregates or after preparation of a sensor tends to self-extinction.
    By using the organic solvents selected from the group consisting of methyl ethyl ketone, chloroform, ethyl acetate or fluorinated organic compounds, e.g. Octofluorotoluene, which is chosen in such a way as to be able to dissolve the respective matrix polymer, makes it possible to produce a sensor ink in which the viscosity can be set exactly to that for a mass printing process, such as flexographic printing, offset printing or ink jet printing. In addition, such solvents are chosen so that it has a boiling point of below 100 ° C, so that a separate drying process for the sensor after its application to the carrier film is not required, but the sensor already inside the printing unit / the printing press in the Drying section provided for this purpose is completely dried, ie the solvent evaporates. In addition, such organic solvents ensure that they leave a homogeneous surface as they evaporate and evaporate uniformly, thereby providing a homogeneous sensor in which the fluorophore molecules are also present in the dried form as discrete molecules which are sufficiently spaced apart from each other Use of the sensor is not prone to self-extinction but give a strong reproducible signal is achievable.
    In particular, in order to prevent self-extinction of the fluorophore or the excited fluorophore molecules in a measurement with certainty, the sensor ink according to the present invention is essentially further developed such that the fluorophore is present in the polymer solution molecularly dissolved. Such a molecular solution can be achieved only by an exact interaction of the selected polymer or homo- or copolymer and the chosen solvent and in particular the polymer and the solvent must be chosen so that not only in solution of the fluorophore is present molecularly dissolved and the Fluorophormoleküle spaced apart, but also after drying a sensor point on the carrier film. In this case, it must be ensured that migration of the fluorophore molecules does not take place in the carrier matrix and that formation of agglomerates can not take place in order to ensure an always consistent, reproducible measurement, which only depends on the concentration of the fluorophore in the polymer and the layer thickness thereof depends.
    The term "molecularly dissolved" is understood to mean that the fluorophore molecules in the polymer solution and in the solidified polymer are present as discrete single molecules and no agglomerates, no adducts and the like are formed.
    By, as this corresponds to a development of the invention, the sensor ink is selected so that the viscosity of the solution for an ink jet pressure between 4 and 20 mPa's is selected, it also succeeds with an ink jet pressure sensor points produce, which always exactly the same thickness or the same size are because a thread pulling pressure is stopped due to the exact set solution viscosity. This method is mainly used for printing containers made of glass or plastic.
    The same applies if, as also corresponds to a development of the invention, the viscosity of the solution for a flexographic printing or offset printing between 15 and 200 mPa's, in particular 20 to 70 mPa's is selected. In mass printing, flexographic printing or offset printing, it is usually necessary to set the viscosity of the solution slightly higher than in ink jet printing in order to be able to produce discrete and reproducible sensor points. In these printing methods as well, it is essential to set the viscosity of the solution such that the individual points thereof can be prevented from drawing off during printing, in order to achieve always reproducible results in which the amount of ink can flow Fluorophore, which is contained in a single sensor point, is reproducible in order to obtain correspondingly reproducible results.
    For this it is favorable that, as corresponds to a development of the invention, the sensor ink is formed so that its elasticity in a visco-elastic system, expressed as G 'at frequencies £ 50 Hz is less than the amount of the viscosity value, printed as G". When setting such an elasticity can be ensured that a printing is done without threading and that a formed with this sensor ink sensor point is sufficiently elastic to follow the movements of the carrier film without breaking or detachment of the same takes place. In order to further avoid peeling, the surface properties of the films on which such sensors are printed can be improved, for example, by a corona treatment.
    Such a sensor ink is suitable for the production of fluorescence sensors by means of mass printing method, according to the invention, a method for producing such a fluorescence sensor essentially characterized in that it comprises the following steps: a) producing a sensor ink according to one of claims 1 to 7 by mixing all components with stirring until a homogeneous solution is formed, b) applying the sensor ink by means of a mass printing process on a heat sealable, a surface tension of> 36 N / m2 having plastic film or a plastic container or a glass container, c) evaporation of the in Sensor ink contained solvent in a printer device, and d) optionally rolling the printed with the sensor ink plastic film into rolls.
    With the method according to the invention, it is possible for the first time to use a sensor ink
    Applying mass printing method to a plastic film or a plastic container or a glass container, which not only succeeds in applying the sensor ink to the film, but in particular makes it possible that due to the specific composition of the sensor ink evaporates the solvent contained in the ink in the drying section of the printer unit or is vaporized and at extremely high printing speeds, a sensor or a plurality of very small thickness sensors can be formed, which are directly available for further use.
    In order to ensure the evaporation of the solvent inside the printer safely and completely, and in particular in the short time it takes for a film to be transported across the dryer section of the printer, the method is further developed such that the evaporation of the solvent in the Inside the printer at a temperature in the printer <90 ° C is performed. At the evaporation temperature below 90 ° C., it is ensured that the abovementioned abovementioned solvents, namely methyl ethyl ketone, ethyl acetate, chloroform or fluorinated organic compounds, are readily evaporated off without leaving residues and without the sensor formed having irregularities, in particular surface roughness or an agglomeration of the fluorophore contained in the sensor takes place.
    Such an ink may be used in particular in a flexographic printing, offset printing or ink jet printing process for printing the ink on a plastic film or a plastic or glass container. With the hitherto known inks, the implementation of such a method was not possible and in particular there was a prejudice that it was not possible to achieve such a rapid drying of the sensor material that a mass printing method could be carried out, since otherwise the individual sides of the film or If the rotations of a roll or the occasional plastic or glass containers stick together, the sensors would be destroyed or torn off.
    Particularly suitable for carrying out the method according to the present invention have, as this corresponds to a development of the invention, films selected from the group polysulfone (PS), polypropylene (PP), polyethylene (PE), polyamide (PA), poly ethylene terephthalate incl. BioPolymere, such as polylactic acid (PLA), polyethylene terephthalate (BioPET), cellophane) proved. Such films are sufficiently flexible to be printed, have sufficient temperature stability so as not to be degraded during printing, and can be thermo-sealed to make, for example, food packaging or medical device packaging.
    In particular, to use the method for the production of fluorescence sensors, which can be used to detect, for example, the oxygen content in packaging or to prove whether a package is tightly sealed, the plastic film is selected according to a preferred embodiment of the method so that it has a high Has oxygen barrier effect. In particular, in this case films can be used which have an oxygen permeability of less than 10 cm 3 / m 2 / day / atm.
    Finally, the invention relates to a sensor, in particular a fluorescence sensor, which is produced by means of a method of the present invention and has been formed inside a package or a vessel which can be sealed by means of a plastic film. Such a sensor is essentially characterized in that the fluorophore is present in the polymer matrix as a discrete dye molecule in an amount of 2 to 5 wt .-% of the polymer matrix and has a thickness of less than 6 pm. Sensors with such small thicknesses could not be produced by the conventional printing methods such as screen printing methods, in particular, it was not possible at the same time to provide a sufficient concentration of the fluorophore in the sensor material and to form an extremely thin sensor. Only by selecting the polymer matrix of the present invention and the solvent and the method of applying the sensor ink to a plastic film according to the present invention, it is possible to produce sensors with such low layer thicknesses and simultaneously large concentrations of fluorophore. Such a sensor according to the present invention can be applied to the carrier foils by means of mass printing media, such as flexographic printing, offset printing or inkjet printing, so that they are suitable for mass production.
    A printing solution according to the invention prepared by the process of the invention contains 16-20% by weight of polymer and 80 to 85% by weight of the solvent. With such a printing solution sensors with thicknesses between 1.5 and 5 pm, preferably 2 to 3 pm can be obtained.
    权利要求:
    Claims (12)
    [1]
    1. sensor ink for a flexographic printing or offset printing, comprising at least one fluorophore, a polymeric carrier matrix and at least one organic solvent, characterized in that as a carrier matrix, a silicon-organic system or a homo- or co-polymer selected from the group polystyrenes, polysulfones, Polyether sulfides, polyether sulfones, polyvinyl chloride (PVC), polyphenylene oxide (PPO), polysulfone derivatives, polyethylene terephthalate, bio-based polymers, polylactic acid, cellulose esters and cellulose ethers having a molecular weight between 80,000 and 300,000, preferably between 100,000 and 240,000, the fluorophore is contained in an amount of 1 , 0 wt .-% to 7 wt .-% based on the polymer concentration is present and that the carrier matrix and the fluorophore with the organic solvent form a viscosity of between 15 and 200 mPa's, in particular 20 to 70 mPa's having solution.
    1. sensor ink comprising at least one fluorophore, a polymeric carrier matrix and at least one organic solvent, characterized in that as a carrier matrix, a silicon-organic system or a homo- or co-polymer selected from the group polystyrenes, polysulfones, polyetherimides, polyethersulfones, polyvinyl chloride ( PVC), polyphenylene oxide (PPO), polysulfone derivatives, polyethylene terephthalate, biobased polymers, polylactic acid, cellulose esters and cellulose ethers having a molecular weight between 80,000 and 300,000, preferably between 100,000 and 240,000, the fluorophore is present in an amount of 1.0 wt. -% to 7 wt .-% based on the polymer concentration is present and that the carrier matrix and the fluorophore with the organic solvent form a viscosity of between 4 and 200 mPa's having solution.
    [2]
    2. sensor ink according to claim 1, characterized in that the fluorophore is selected from the group: metal porphyrins, Phenanthrolinkomplexe, such as diphenylphenantroline, Ru thenium (II) complexes, fluorescein derivatives, coumarin derivatives and phenylmethane.
    2. sensor ink according to claim 1, characterized in that the fluorophore is selected from the group: metal porphyrins, Phenanthrolinkomplexe, such as diphenylphenantroline, Ru thenium (II) complexes, fluorescein derivatives, coumarin derivatives and phenylmethane.
    [3]
    3. sensor ink according to claim 1 or 2, characterized in that the organic solvent is selected from the group: methyl ethyl ketone, chloroform, ethyl acetate or fluorinated organic compounds.
    3. sensor ink according to claim 1 or 2, characterized in that the organic solvent is selected from the group: methyl ethyl ketone, chloroform, ethyl acetate or fluorinated organic compounds.
    [4]
    4. sensor ink according to claim 1, 2 or 3, characterized in that the fluorophore is present dissolved in the polymer solution molecular.
    4. sensor ink according to claim 1, 2 or 3, characterized in that the fluorophore is present dissolved in the polymer solution molecular.
    [5]
    5. sensor ink according to one of claims 1 or 4, characterized in that its elasticity in a visco-elastic system, expressed as G 'at frequencies <50 Hz is less than the amount of the viscosity value, expressed as G ".
    5. sensor ink according to claim 1, characterized in that the viscosity of the solution for an ink jet pressure between 4 and 20 mPa's is selected.
    [6]
    6. A method for producing a fluorescence sensor, characterized in that it comprises the following steps: a) producing a sensor ink according to one of claims 1 to 5 by mixing all the ingredients with stirring until a homogeneous solution is formed, b) applying the sensor ink by means a mass-printing process on a heat-sealable, a surface tension of> 36 N / m2 having plastic film or a glass container, c) evaporation of the solvent contained in the sensor ink, and d) optionally rolling the printed with the sensor ink plastic film into rolls.
    6. sensor ink according to claim 1, characterized in that the viscosity of the solution for a flexographic printing or offset printing between 15 and 200 mPa's, in particular 20 to 70 mPa's is selected.
    [7]
    7. The method according to claim 6, characterized in that the evaporation of the solvent in the interior of the printer at a temperature present in the printer <90 ° C is performed.
    7. sensor ink according to claim 5 or 6, characterized in that its elasticity in a visco-elastic system, expressed as G 'at frequencies £ 50 Hz is less than the amount of the viscosity value, expressed as G ".
    [8]
    8. The method according to claim 6 or 7, characterized in that the sensor ink is applied by a method selected from flexographic or offset printing on the plastic film, plastic or glass containers.
    8. A method for producing a fluorescence sensor, characterized in that it comprises the following steps: a) producing a sensor ink according to one of claims 1 to 7 by mixing all the ingredients with stirring until a homogeneous solution is formed, b) applying the sensor ink by means a mass-printing process on a heat-sealable, a surface tension of> 36 N / m2 having plastic film or a glass container, c) evaporation of the solvent contained in the sensor ink, and d) optionally rolling the printed with the sensor ink plastic film into rolls.
    [9]
    9. The method according to any one of claims 6, 7 or 8, characterized in that the film to be printed is selected from the group: polysulfone (PS), polypropylene (PP), polyethylene (PE), polyamide (PA), polyethylene terephthalate incl. Bio-polymers such as polylactic acid (PLA), polyethylene terephthalate (BioPET), cellophane).
    9. The method according to claim 8, characterized in that the evaporation of the solvent in the interior of the printer at a temperature present in the printer <90 ° C is performed.
    [10]
    10. The method according to claim 9, characterized in that a plastic film with high oxygen barrier effect or an oxygen permeability of less than 10 cm3 / m2 / day / atm is used.
    10. The method according to claim 8 or 9, characterized in that the sensor ink is applied by a method selected from flexographic printing, offset printing or inkjet printing on the plastic film, plastic or glass containers.
    [11]
    11. Sensor, in particular fluorescence sensor, produced by a method according to one of claims 6 to 9 on a heat-sealable plastic film or plastic container or a glass container, characterized in that the fluorophore in the polymer matrix as discrete dye molecules in an amount of 2 to 5 wt .-% of the polymer matrix is present.
    11. The method according to any one of claims 8, 9 or 10, characterized in that the film to be printed is selected from the group: polysulfone (PS), polypropylene (PP), polyethylene (PE), polyamide (PA), polyethylene terephthalate incl. Bio-polymers such as polylactic acid (PLA), polyethylene terephthalate (BioPET), cellophane).
    12. The method according to claim 11, characterized in that a plastic film with high oxygen barrier effect or an oxygen permeability of less than 10 cm3 / m2 / day / atm is used.
    13. Sensor, in particular fluorescence sensor, produced by a method according to one of claims 8 to 11 on a heat-sealable plastic film or plastic container or a glass container, characterized in that the fluorophore in the polymer matrix as discrete dye molecules in an amount of 2 to 5 wt .-% of the polymer matrix is present.
    14. Sensor according to claim 13, characterized in that a layer cover of a dried sensor ink on the plastic film is less than 6 pm, in particular less than 5 pm. claims:
    [12]
    12. Sensor according to claim 11, characterized in that a layer cover of a dried sensor ink on the plastic film is less than 6 pm, in particular less than 5 pm.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US4186020A|1974-11-04|1980-01-29|A. B. Dick Company|Fluorescent ink for automatic identification|
    WO1998018871A1|1996-10-28|1998-05-07|Eastman Chemical Company|Organic solvent based ink for invisible marking/identification|
    US7947772B2|2004-11-10|2011-05-24|The Regents Of The University Of Michigan|Multiphasic nano-components comprising colorants|
    US20100143675A1|2006-11-20|2010-06-10|Adrian Guckian|Inks and coatings for the production of oxygen sensitive elements with improved photostability|
    JP6024040B2|2012-09-20|2016-11-09|ゼネラル株式会社|Non-aqueous inkjet ink and ink set|
    US10377901B2|2014-08-12|2019-08-13|Georgia State University Research Foundation, Inc.|Near infrared absorbing fluorescent compositions|CN110596070A|2019-10-24|2019-12-20|哈尔滨工业大学|Use of ratiometric oxygen sensing membranes for gaseous oxygen detection|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    ATA422/2017A|AT520591B1|2017-10-30|2017-10-30|Sensor ink, method for producing a fluorescence sensor with the sensor ink and sensor|ATA422/2017A| AT520591B1|2017-10-30|2017-10-30|Sensor ink, method for producing a fluorescence sensor with the sensor ink and sensor|
    JP2020543653A| JP2021501256A|2017-10-30|2018-10-25|Sensor ink for detecting components in hermetically sealed packaging, methods and sensors for manufacturing fluorescent sensors containing the sensor ink|
    PCT/AT2018/000088| WO2019084582A1|2017-10-30|2018-10-25|Sensor ink for detecting components in sealed packagings, process for producing a fluorescence sensor comprising the sensor ink and sensor|
    CA3081101A| CA3081101A1|2017-10-30|2018-10-25|Sensor ink for detecting components in sealed packaging, process for producing a fluorescent sensor comprising the sensor ink and sensor|
    RU2020117607A| RU2020117607A3|2017-10-30|2018-10-25|
    US16/760,051| US20200347255A1|2017-10-30|2018-10-25|Sensor ink for detecting components in sealed packaging process for producing a fluorescence sensor comprising the sensor ink and sensor|
    EP18450009.8A| EP3476908A1|2017-10-30|2018-10-25|Sensor ink, method for producing a fluorescence sensor with the sensortine and sensor|
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