WO2021110210A1 - Utilisation de liquides ioniques dans une composition d'apprêt - Google Patents

Utilisation de liquides ioniques dans une composition d'apprêt Download PDF

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Publication number
WO2021110210A1
WO2021110210A1 PCT/DE2020/101011 DE2020101011W WO2021110210A1 WO 2021110210 A1 WO2021110210 A1 WO 2021110210A1 DE 2020101011 W DE2020101011 W DE 2020101011W WO 2021110210 A1 WO2021110210 A1 WO 2021110210A1
Authority
WO
WIPO (PCT)
Prior art keywords
oxide
primer composition
weight
primer
ionic liquid
Prior art date
Application number
PCT/DE2020/101011
Other languages
German (de)
English (en)
Inventor
Danjo LEPPIG
Sven Michael
Wolfgang Cordroch
Thomas Boosmann
Original Assignee
Windmöller & Hölscher Kg
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 Windmöller & Hölscher Kg filed Critical Windmöller & Hölscher Kg
Priority to JP2022534209A priority Critical patent/JP2023505296A/ja
Priority to EP20853557.5A priority patent/EP4069770A1/fr
Publication of WO2021110210A1 publication Critical patent/WO2021110210A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring

Definitions

  • the present invention relates to a primer composition and the use thereof in the production of a primer layer on a carrier in preparation for a digital printing process.
  • Plastic films for example made of polypropylene (PP) or polyethylene (PE), basically have a non-polar property, which makes printing with water-soluble and therefore polar ink difficult.
  • Primer ”
  • PP polypropylene
  • PE polyethylene
  • Prior art water-based primer compositions for the production of primers, ie communication layers comprise not only water but also substantial amounts of low-boiling organic solvents (VOC, volatile organic compounds), usually in amounts of about 20-50% by weight. These VOCs are released during the production of the primer layer or the subsequent drying.
  • VOC low-boiling organic solvents
  • VOCs are often harmful to health. In particular in mass production, this results in problems due to high VOC emissions at the workplace. In addition, the release of VOCs can lead to the formation of explosive and / or flammable mixtures. Finally, there is a need for improvement of corresponding products that comprise a corresponding primer layer with regard to adhesion and chemical resistance.
  • a primer composition comprising: a) 50-97.5% by weight of water; b) 1-48.5% by weight of an ionic liquid; c) 1-30% by weight of an inorganic oxide, a polymer compound, or a mixture of 2 or more thereof; and d) 0.5-10% by weight of a polar organic compound; each based on the total weight of the primer composition.
  • VOCs low-boiling organic solvents
  • the primer composition according to the invention is an aqueous primer composition.
  • the primer composition can be used in preparation for a digital printing process.
  • the preparation of a digital printing process is in particular the application of a primer layer to a carrier in order to facilitate the printing of the carrier in the digital printing process, e.g. in the inkjet printing process using a suitable ink composition, in particular to improve the adhesion of the ink to the carrier.
  • the aqueous primer composition comprises at least 50% by weight of water, based on the total weight of the composition.
  • the aqueous primer composition contains at least 60% by weight of water, alternatively at least 70% by weight, in each case with regard to the total weight of the composition.
  • the primer composition contains water in an amount of at most 95% by weight, alternatively at most 90% by weight, alternatively at most 85% by weight, alternatively at most 80% by weight, each based on the total weight of the Primer composition contains.
  • the ionic liquid is present in an amount of at least 2% by weight, alternatively at least 3% by weight, alternatively at least 4% by weight, alternatively at least 5% by weight is contained in the primer composition It can also be provided that the ionic liquid in the primer composition is at most 45% by weight, alternatively at most 40% by weight, alternatively at most 30% by weight , alternatively a maximum of 20% by weight, alternatively a maximum of 10% by weight, alternatively a maximum of 8% by weight. The percentages relate in each case to the total weight of the primer composition.
  • the inorganic oxide, the polymer compound or the mixture of two or more thereof in a total amount of at least 2% by weight, alternatively at least 4% by weight, alternatively at least 8% by weight, alternatively at least 10% by weight % By weight is contained in the primer composition. It can also be provided that the inorganic oxide, the polymer compound or the mixture of two or more thereof in a total amount of at most 25% by weight, alternatively at most 20% by weight, alternatively at most 17.5% by weight, alternatively at most 15% by weight is contained in the primer composition. The percentages here relate in each case to the total weight of the primer composition.
  • An ionic liquid is an ionic compound (salt) comprising one or more anions and one or more cations, preferably an anion and a cation, which is preferably at a temperature of 200 ° C. or less, preferably 150 ° C. or less, moreover 100 ° C or less, is liquid without the salt being dissolved in a solvent such as water.
  • the ionic liquid has a melting point which is above 60 ° C. Ionic liquids are completely miscible with water. Ionic liquids have no (measurable) vapor pressure, so they are not released into the gas phase even at high temperatures.
  • Exemplary cations that can be contained in the ionic liquid according to the invention are in particular imidazolium, pyridinium, pyrrolidinium, phosphonium, ammonium, guanidinium, uronium or thiouronium. These cations are preferably alkylated cations.
  • Anions according to the invention are, for example, halides and more complex ions such as tetralfluoroborates, trifluoroacetate, triflate, hexafluorophosphate, phosphinate and tosylate.
  • Organic anions for example imides or amides, can also be provided.
  • Preferred anions are I-, Cl-, Br-, SCN-, BF 4 -, PF 6 -, ClO 4 -, SbF 6 - (CF 3 S0 2 ) 2 N-, (CF 3 CF 2 S0 a ) z N -, Ph 4 B-, (C 2 H 4 O 2 B-, (CF 3 SO 2 ) 3 C-, CF 3 COO-, CF 3 SO 3 -.
  • the ionic liquid is an imidazonium salt.
  • the imidazolium is a dialkylimidazolium of the following formula where R 1 and R 2 are independently selected from the group consisting of C 1 -C 8 -alkyl, preferably C 1 -C 6 -alkyl, preferably C 1 -C 4 -alkyl, particularly preferably C 1 -C 3 -alkyl most preferably C 1 -C 2 alkyl.
  • the ionic liquid is 1-ethyl-3-methylimidazoUum tetrafluoroborate.
  • the inorganic oxide is a colloidal inorganic oxide.
  • the polymer compound is in the form of a colloid.
  • a colloid is a finely divided substance that is in the form of discrete particles.
  • the inorganic oxide or the polymer compound is present in the form of particles.
  • the BET surface area of the particles determined in accordance with DIN ISO 5794/1 Annex D with Na, is from 10 to 550 m 2 / g, preferably 25 to 350 m 2 / g.
  • the particles of the inorganic oxide / polymer compound have an average particle diameter of from 2 to 20 ⁇ m, preferably from 5 to 20 ⁇ m. Reference is made here to an average particle diameter determined by means of a Coulter Counter, Model TA ⁇ from Coulter Electronics, determined using the 100 ⁇ m capillary.
  • the inorganic oxide is selected from the group consisting of silicon dioxide, titanium dioxide, zinc oxide, tin oxide, aluminum oxide, indium oxide, magnesium oxide, barium oxide, molybdenum oxide, tungsten oxide, vanadium oxide and a mixture of two or more thereof, preferably Silicon dioxide.
  • the inorganic oxide is precipitated silica
  • precipitated silica is precipitated silica (precipitated silicon dioxide) is an amorphous form of silicon dioxide in the form of a white, powdery material, obtainable by precipitation from a solution containing silicate.
  • Precipitated silica is produced in particular by condensation of silica from dilute alkali silicate solutions
  • the polymer compound can in particular be a colloidal polymer material. It can be provided that this is a hydrophilic colloidal material that comprises a water-soluble polymer. According to the invention it can be provided that the polymer compound, which can be present in the form of a colloidal material, is one or more selected from polyvinyl compounds, some polyvinyl alcohol, polyacrylamide, Polymethacrylamide, poly (N, N-dimethylacrylamide), poly (n-isopropylacrylamide),
  • the polar organic compound comprises two to 18 carbon atoms, preferably two to ten carbon atoms, more preferably two to six carbon atoms, particularly preferably 4 carbon atoms.
  • the polar inorganic compound comprises at least one carboxyl group.
  • the polar organic compound comprises two carboxyl groups.
  • the polar organic compound is tartaric acid.
  • the primer composition contains an organic solvent in an amount of 10% by weight or less, based on the total weight of the primer composition. In a further embodiment it can be provided that the primer composition comprises organic solvent in an amount of 5% by weight or less.
  • Organic solvents in the context of the invention are in particular volatile organic compounds (VOC) and very volatile organic compounds (VVOC).
  • Organic solvents for the purposes of the present invention are, in particular, polar organic solvents, i.e. solvents that are soluble in water.
  • Organic solvents within the meaning of the present invention include in particular DMSO, monoalcohols, polyalcohols, polyalcohols of lower alkyl ethers , Ketones, ethers, esters, nitrogen-containing solvents etc.
  • the primer composition according to the invention comprises no organic solvent or only in an amount of 5% by weight or less, based on the total weight, and the ionic liquid in an amount of at least 5% by weight based on the total weight of the composition
  • the object is also achieved by a method for printing a carrier using the digital printing process, comprising: a) providing the carrier; b) applying a primer layer to at least one surface of the carrier using the primer compositions according to one of the preceding claims; and c) printing the carrier in the digital printing process on the at least one surface which is coated with the primer layer
  • a plastic film can in particular be provided as the carrier according to the invention.
  • the plastic film is a film made of polyethylene, polypropylene or mixtures thereof.
  • the digital printing process which is used in the process according to the invention, as well as the process in which the composition according to the invention is used as ink can be any digital printing process known from the prior art, for example an inkjet printing process.
  • the object is achieved by the use of the primer composition according to the invention for producing a primer layer on a carrier for the preparation of a digital printing process.
  • a prior art primer composition was prepared by mixing the following ingredients.
  • a primer composition according to the present invention was prepared by mixing the following ingredients.
  • Ethylmethylimidazole BF 4 (emimbf 4 ) 5% by mass precipitated silica 12.5% by mass 2,3-dihydroxybutanedioic acid 3% by mass 1,2-benzoisothiazolin-3-one 0.2% by mass
  • the primer composition according to the invention differs from the primer composition according to the prior art (comparative example) in that the organic solvent (DMSO) used in large quantities according to the prior art is partially replaced by an ionic liquid (1-ethyl-3- methylimidazolium tetrafluoroborate) was replaced.
  • DMSO organic solvent
  • the primer compositions according to the example and according to the comparative example were applied to a plastic film in preparation for an inkjet print and then tested for their adhesion and chemical resistance.
  • the assessment is based on the following scale:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

La présente invention concerne une composition d'apprêt comprenant : a) 50 à 97,5 % en poids d'eau ; b) 1 à 48,5 % en poids d'un liquide ionique ; c) 1 à 30 % en poids d'un oxyde inorganique, d'un composé polymère ou d'un mélange d'au moins 2 de ces constituants ; et d) 0,5 à 10 % en poids d'un composé organique polaire, respectivement par rapport au poids total de la composition d'apprêt, ainsi que l'utilisation de cette composition pour la préparation d'un support pour un procédé d'impression numérique.
PCT/DE2020/101011 2019-12-04 2020-12-01 Utilisation de liquides ioniques dans une composition d'apprêt WO2021110210A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2022534209A JP2023505296A (ja) 2019-12-04 2020-12-01 プライマー組成物におけるイオン液体の使用
EP20853557.5A EP4069770A1 (fr) 2019-12-04 2020-12-01 Utilisation de liquides ioniques dans une composition d'apprêt

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102019132984.1 2019-12-04
DE102019132984.1A DE102019132984A1 (de) 2019-12-04 2019-12-04 Verwendung von ionischen Flüssigkeiten in Primer-Zusammensetzung

Publications (1)

Publication Number Publication Date
WO2021110210A1 true WO2021110210A1 (fr) 2021-06-10

Family

ID=74625766

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE2020/101011 WO2021110210A1 (fr) 2019-12-04 2020-12-01 Utilisation de liquides ioniques dans une composition d'apprêt

Country Status (4)

Country Link
EP (1) EP4069770A1 (fr)
JP (1) JP2023505296A (fr)
DE (1) DE102019132984A1 (fr)
WO (1) WO2021110210A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060052493A1 (en) * 2004-09-03 2006-03-09 Toshiaki Nagano Paint compositions
WO2007077057A1 (fr) * 2006-01-03 2007-07-12 Degussa Ag Compositions utilisees de maniere universelle
EP3099754A1 (fr) * 2014-01-31 2016-12-07 Trüb Emulsions Chemie AG Revêtement d'impression de type aqueux utilisable dans un procédé d'impression numérique
WO2017097371A1 (fr) * 2015-12-11 2017-06-15 Hewlett-Packard Indigo B.V. Préparation de substrat d'impression
WO2017106407A1 (fr) * 2015-12-18 2017-06-22 Michelman, Inc. Revêtements imprimables à base d'ionomères

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060052493A1 (en) * 2004-09-03 2006-03-09 Toshiaki Nagano Paint compositions
WO2007077057A1 (fr) * 2006-01-03 2007-07-12 Degussa Ag Compositions utilisees de maniere universelle
EP3099754A1 (fr) * 2014-01-31 2016-12-07 Trüb Emulsions Chemie AG Revêtement d'impression de type aqueux utilisable dans un procédé d'impression numérique
WO2017097371A1 (fr) * 2015-12-11 2017-06-15 Hewlett-Packard Indigo B.V. Préparation de substrat d'impression
WO2017106407A1 (fr) * 2015-12-18 2017-06-22 Michelman, Inc. Revêtements imprimables à base d'ionomères

Also Published As

Publication number Publication date
JP2023505296A (ja) 2023-02-08
DE102019132984A1 (de) 2021-06-10
EP4069770A1 (fr) 2022-10-12

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