WO2008098799A1 - Revêtement anti-graffiti - Google Patents

Revêtement anti-graffiti Download PDF

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Publication number
WO2008098799A1
WO2008098799A1 PCT/EP2008/050076 EP2008050076W WO2008098799A1 WO 2008098799 A1 WO2008098799 A1 WO 2008098799A1 EP 2008050076 W EP2008050076 W EP 2008050076W WO 2008098799 A1 WO2008098799 A1 WO 2008098799A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
zonyl
meth
acrylate
coating
Prior art date
Application number
PCT/EP2008/050076
Other languages
German (de)
English (en)
Inventor
Patrick Becker
Waldemar Kanzler
Margarita Stein
Ghirmay Seyoum
Claudius Neumann
Original Assignee
Evonik Röhm Gmbh
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 Evonik Röhm Gmbh filed Critical Evonik Röhm Gmbh
Publication of WO2008098799A1 publication Critical patent/WO2008098799A1/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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/123—Treatment by wave energy or particle radiation

Definitions

  • the present invention relates to coating compositions for the production of deformable scratch-resistant coatings with dirt-repellent action, molded articles coated with these coating compositions with a scratch-resistant, formable and dirt-repellent coating and to processes for producing the coated molded bodies.
  • thermoplastically deformable plastics do not achieve the scratch resistance of many metals or mineral glasses. Particularly disadvantageous is the susceptibility to scratches in transparent plastics noticeable, since the objects in question are very quickly unsightly.
  • Plastic moldings also scratch-resistant coated, mainly used in the form of panels in the construction exterior, such as noise barriers or as glazings of facades, bus stops, advertising space, Litank columns, so-called “mobile urban”, where they are both natural pollution than also caused by vandalism impurities, such as the graffiti smear are exposed.
  • the cleaning of such surfaces is very expensive, since often the surface is attacked by this.
  • fluorine-containing acrylates are frequently added to the coating compositions.
  • Such coating compositions are described for example in DE 43 19 199.
  • a disadvantage of known coating compositions is that coatings produced therefrom form cracks on plastic bodies during thermal deformation, the coating on the formed body becoming milky and unsightly.
  • Structural parts are made for much wider customer circles than preformed plates made specifically for a customer.
  • the aim was to develop a coating that allows both a low surface energy in the range of 22-27 mN / m, as well as a good cleanability with water pressure washer without the coating being attacked or injured (no flaking, etc.) ,
  • the purpose of the coating is to protect the articles coated with the paint against graffiti attacks, i. that applied paint can be easily removed with a high-pressure cleaner.
  • plastic body with a scratch-resistant coating according to the invention have a high durability, in particular a high resistance to UV irradiation or weathering.
  • Another object of the present invention was to provide antigraffiti-effect coating agents which do not adversely affect the properties of the substrate.
  • the spray paints used to make graffiti should no longer or only very weakly adhere to the plastic body by an antigraffiti finish according to the invention, wherein sprayed substrates should be easy to clean, so that e.g. Water, cloths, surfactants, high pressure cleaners, mild solvents ("easy-to-clean”) are sufficient.
  • the invention has for its object to provide scratch-resistant, dirt-repellent moldings available, which can be produced particularly easily. So should for the production of the moldings in particular Substrates can be used, which are available by extrusion, injection molding and casting.
  • a further object of the present invention was to provide scratch-resistant, formable, dirt-repellent moldings which show excellent mechanical properties. This property is particularly important for applications in which the plastic body should have a high stability against impact.
  • the moldings should have particularly good optical properties.
  • a further object of the present invention was to provide scratch-resistant, formable, dirt-repellent moldings which can be easily adapted to the requirements in a larger form.
  • the products are sold under the brand names Zonyl ® TA-N (fluoroalkyl) and Zonyl ® TM (fluoroalkyl) DuPont commercialized.
  • PLEX ® 8770 F is a prepolymer, available from Rohm GmbH, a copolymer of methyl methacrylate and pentaerythritol tetrathioglycolate understood. Particularly preferred is a prepolymer of:
  • Pentaerythritol tetrathioglycolate 5% pentaerythritol tetrathioglycolate.
  • Byk 045 is understood to mean a course additive.
  • Tinuvin R769 is understood to mean a UV absorber.
  • Irgacure 184 is understood to mean photoinitiator.
  • no anti-graffiti effect means a water contact angle ⁇ 90 °.
  • test conditions for the adhesion test of the coating were chosen as follows:
  • Distance nozzle - Substrate Between 15 and 12 cm. It is tested by means of a high-pressure cleaner in the area of the cross-hatch. After applying the high-pressure cleaner, the area of the cross-hatch is examined for any paint chips according to DIN 53151. The Gt classification from 0 to 5 applies here. A test with crosshatching and adhesive tape can not be used in this test, since the very low surface energy of the antigraffiti coating is not sufficient to produce sufficient adhesion to the adhesive film. Thus, the adhesion between Tesafilm and coating is not significant.
  • the coating For the coating to meet the criteria of the high-pressure cleaner test, u.U. the enriched on the surface of the plastic release agent are removed.
  • the Zonyl ® TA-N completely converted to a concentration of 2% at room temperature in solution.
  • Examples of the C 1 - to C 8 -alkyl esters of acrylic acid or methacrylic acid are methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate and its isomers, n-hexyl (meth) acrylate and its isomers and 2-ethylhexyl (meth) acrylate, heptyl (meth) acrylate and its isomers, octyl (meth) acrylate and isooctyl (meth) acrylate.
  • Preferred monomers are methyl methacrylate and n-butyl acrylate.
  • Zonyl® T-AN / TM completely dissolves up to 10% by weight in butyl acrylate
  • Zonyl ® TA-N / TM dissolves completely up to 7 wt .-% in vinyl methacrylate
  • the polarity of the monomer mixture of the base formulation affects the solubility of the zonyl.
  • the length of the alkyl radical and the functionality of the ester are crucial. For bi- and polyfunctional acrylate crosslinkers, precipitation of zonyl is observed.
  • the paint formulation may be modified with regard to the polarity.
  • the paint system is insensitive to temperature fluctuations. Moreover, the coating with full Zonyl ® solubility is much higher weather resistance of the anti-graffiti effect (s. Fig. 6)
  • the conditions during the UV polymerization process are crucial. If the UV polymerization takes place at a dose D ⁇ 2,000 mJ / cm 2 or at D> 3,500 mJ / cm 2 , this has a disadvantageous effect on the weathering resistance of the active effect. Deviations are already observed after 3 months of natural weathering in Australia. Only in the interval of 2,000 mJ / cm 2 ⁇ D ⁇ 3,500 mJ / cm 2 , the HPPs remain at> 90 ° after 3 months of weathering at HPC.
  • Curing parameters 140W / cm emitter output, 3m / min belt speed, ⁇ 300 ppm O2 at the Print-Concept-System (UV-polymerisation system)
  • Plexiglas ® plates or films can be used as substrates Plexiglas ® plates or films.
  • the coated substrates can be used for example as components in noise barriers, the coated films can be used to provide objects with easy-to-clean surfaces.
  • Figure 6 Comparison of the weather resistance of the anti-graffiti effect between AG200VL (paint formulation with 2% of complete Zonyl ® TA-N solution) with AG140ZA (current paint formulation) in the outdoor weathering Australia.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une composition de revêtement ayant un effet anti-graffiti. La composition selon l'invention est constituée ainsi : 1 à 50 % en poids d'un prépolymérisat ; 0,2 à 48 % en poids d'au moins un fluoroalkyl(méth)acrylate portant 6 à 20 atomes de carbone dans le radical alcool contenant 13 à 42 atomes de fluor ; 20 à 80 % en poids de (méth)acrylates polyvalents, 0,01 à 10 % en poids d'au moins un initiateur, 2 à 75 % en poids d'au moins un diluant, et 0 à 40 % en poids d'additifs habituels.
PCT/EP2008/050076 2007-02-15 2008-01-07 Revêtement anti-graffiti WO2008098799A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200710007999 DE102007007999A1 (de) 2007-02-15 2007-02-15 Antigraffiti Beschichtung
DE102007007999.2 2007-02-15

Publications (1)

Publication Number Publication Date
WO2008098799A1 true WO2008098799A1 (fr) 2008-08-21

Family

ID=39186985

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/050076 WO2008098799A1 (fr) 2007-02-15 2008-01-07 Revêtement anti-graffiti

Country Status (3)

Country Link
DE (1) DE102007007999A1 (fr)
TW (1) TW200838954A (fr)
WO (1) WO2008098799A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009000450A1 (de) 2009-01-28 2010-07-29 Evonik Degussa Gmbh Transparente, witterungsbeständige Barrierefolie, Herstellung durch Lamination, Extrusionslamination oder Extrusionbeschichtung
CN105482604B (zh) * 2015-12-26 2017-08-25 杭州吉华高分子材料股份有限公司 一种水性防涂鸦涂料及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0628610A1 (fr) * 1993-06-09 1994-12-14 Röhm Gmbh Revêtement résistant à l'abrasion antisalissant et anti-graffiti pour masses de moulage
DE102004062773A1 (de) * 2004-12-21 2006-06-22 Röhm GmbH & Co. KG Beschichtungsmittel zur Herstellung von umformbaren Kratzfestbeschichtungen mit schmutzabweisender Wirkung, kratzfeste umformbare schmutzabweisende Formkörper sowie Verfahren zu deren Herstellung
DE102005009209A1 (de) * 2005-02-25 2006-08-31 Röhm GmbH & Co. KG Beschichtungsmittel zur Herstellung von umformbaren Kratzfestbeschichtungen mit schmutzabweisender Wirkung, kratzfeste umformbare schmutzabweisende Formkörper sowie Verfahren zu deren Herstellung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE36294E (en) * 1993-06-09 1999-09-07 Rohm Gmbh Chemische Fabrik Scratch-resistant coating agent based on arcylates
DE19507174A1 (de) 1995-03-02 1996-09-05 Roehm Gmbh UV-härtbare Kratzfestlacke mit einpolymerisierendem Verdicker
DE10260067A1 (de) * 2002-12-19 2004-07-01 Röhm GmbH & Co. KG Beschichtungsmittel zur Herstellung von umformbaren Kratzfestbeschichtungen mit schmutzabweisender Wirkung, kratzfeste umformbare schmutzabweisende Formkörper sowie Verfahrn zu deren Herstellung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0628610A1 (fr) * 1993-06-09 1994-12-14 Röhm Gmbh Revêtement résistant à l'abrasion antisalissant et anti-graffiti pour masses de moulage
DE102004062773A1 (de) * 2004-12-21 2006-06-22 Röhm GmbH & Co. KG Beschichtungsmittel zur Herstellung von umformbaren Kratzfestbeschichtungen mit schmutzabweisender Wirkung, kratzfeste umformbare schmutzabweisende Formkörper sowie Verfahren zu deren Herstellung
DE102005009209A1 (de) * 2005-02-25 2006-08-31 Röhm GmbH & Co. KG Beschichtungsmittel zur Herstellung von umformbaren Kratzfestbeschichtungen mit schmutzabweisender Wirkung, kratzfeste umformbare schmutzabweisende Formkörper sowie Verfahren zu deren Herstellung

Also Published As

Publication number Publication date
DE102007007999A1 (de) 2008-08-21
TW200838954A (en) 2008-10-01

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