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WO2018146031A1 - Composition de peinture pour impression en relief, surface microstructurée réalisée à partir de celle-ci et élément d'avion comportant une telle surface microstructurée - Google Patents

Composition de peinture pour impression en relief, surface microstructurée réalisée à partir de celle-ci et élément d'avion comportant une telle surface microstructurée Download PDF

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Publication number
WO2018146031A1
WO2018146031A1 PCT/EP2018/052747 EP2018052747W WO2018146031A1 WO 2018146031 A1 WO2018146031 A1 WO 2018146031A1 EP 2018052747 W EP2018052747 W EP 2018052747W WO 2018146031 A1 WO2018146031 A1 WO 2018146031A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition according
embossing lacquer
lacquer composition
embossing
absorber
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.)
Ceased
Application number
PCT/EP2018/052747
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German (de)
English (en)
Inventor
Dieter Nees
Johannes Götz
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.)
Lufthansa Technik AG
Original Assignee
Lufthansa Technik AG
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 Lufthansa Technik AG filed Critical Lufthansa Technik AG
Priority to EP18707629.4A priority Critical patent/EP3580611A1/fr
Publication of WO2018146031A1 publication Critical patent/WO2018146031A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B64—AIRCRAFT; AVIATION; COSMONAUTICS
    • B64C—AEROPLANES; HELICOPTERS
    • B64C21/00—Influencing air flow over aircraft surfaces by affecting boundary layer flow
    • B64C21/10—Influencing air flow over aircraft surfaces by affecting boundary layer flow using other surface properties, e.g. roughness
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T50/00—Aeronautics or air transport
    • Y02T50/10—Drag reduction

Definitions

  • the present invention relates to a refgelackzusammenset ⁇ requisite for riblet structures based on a prepolymer composition made therefrom a microstructured surface and an aircraft component having such a micro-structured surface ⁇ .
  • Microstructured surfaces are advantageous for a variety of applications.
  • Known examples are so-called flow-favorable riblet structures on surfaces of parts moving relative to a fluid or other medium, for example outer surfaces of aircraft, ships or rotor blades of wind turbines.
  • Such structures are also used, for example, on inner surfaces of pipelines.
  • NIL nanoimprint lithography
  • a polymer composition is patterned by mechanical embossing.
  • This is a high-precision Retriel ⁇ drive, in which it is possible to form even the smallest structures on an appropriate substrate.
  • films having a mikrostruktu ⁇ tured surface can be provided, which are subsequently glued to ent ⁇ speaking surface in this manner substrates.
  • R2R-UV-NIL micro- and nanostructured surfaces such as riblet foils for flow friction reduction can be produced over a large area and at low cost with high throughput.
  • the starting material located on a roll is unrolled on a web of, for example, substrate film at generally high speeds, processed and finally rolled up again. Suitable starting materials can be corresponding pre ⁇ lacquers.
  • EP 2 590 801 B1 discloses a micro- and / or nanostructured surface which is obtained from an acrylate-containing precursor comprising a crosslinkable oligomeric and / or polymeric compound, a reactive diluent, hydrophobic additives and a photoinitiator.
  • NIL embossing lacquers have been optimized for all own sheep ⁇ th as moldability, embossing fidelity, refractive index or ⁇ tzsta ⁇ bility for the structuring of sub-layers.
  • the present invention is therefore based on the object, an embossing lacquer composition and a microstructured To provide surfaces that have due to UV stabilization an increased life and less embrittlement and no yellowing (yellowing).
  • a permanent UV stabilization of (UV) IL embossing lacquers for riblet films is to be made possible in order to reduce the flow friction of commercial aircraft.
  • the invention achieves this object by the inventive embossing lacquer composition for riblet structures based on a prepolymer composition which comprises a system consisting of: a) at least one photoinitiator having a Absorpti ⁇ ons Suite in the longwave UV range and b) at least one UV absorber.
  • embossing lacquer based on a prepolymer composition comprises tung material, any suitable polymerizable coating, the be applied by means of a suitable device to a substrate surface and can there th to mik ⁇ ro gleich believing surface, in particular riblet structured surface cure.
  • a prepolymer composition is a kind of intermediate based on monomers, oligomers and / or polymers to understand that only by curing (ie polymerization) yields the final polymerized product.
  • the curing of the embossing lacquer is preferably carried out by means of UV radiation.
  • all other curing mechanisms known to those skilled in the art may additionally be used.
  • a thermal curing may occur, especially in so-called dual-cure systems.
  • the desired microstructured surface is produced in the already applied embossing lacquer before or during its curing.
  • the embossing lacquers are suitable for use in roll-to-roll, roll-to-plate or sheet-to-sheet processes.
  • the embossing lacquers are particularly preferably used in roll-to-roll UV-NIL processes and have very good impression properties.
  • an absorption region is in the long-wave UV range, preferably a UV range between 340 and 400 nm.
  • Long-wave UV range also means in particular that the absorption range of the photoinitiator must not absorb significantly in the visible range (400 to 800 nm) with wavelengths greater than 400 nm. Otherwise remaining photoinitiator residues lead to yellowing of the embossing lacquer. This applies in particular to colorless paints.
  • the at least one further photoinitiator should also be noted that its decomposition products are not in the visible region absorbie ⁇ ren. For the corresponding decomposition products in many light-curing coating compositions the main reason for yellowing.
  • a photoinitiator having an absorption range in the long-wave UV range between 350 and 390 nm, most preferably between 360 and 385 nm.
  • the at least one photoinitiator and the at least one UV absorber no have overlapping absorption areas.
  • the invention is preferably provided that is Wenig ⁇ least one selected from organic UV absorbers and / or inorganic UV absorbers.
  • the necessary absorption spectrum of the UV stabilizer stabilizing the embossing lacquer is predetermined by the solar spectrum.
  • the organic UV absorber is selected from the group consisting of hydroxyphenyltriazines (HTP), hydroxybenzotriazoles (HBT) and mixtures thereof. Particularly preferred are substituted 2-hydroxyphenyltriazines.
  • the organic UV absorbers are preferably used in a mole fraction of about 2% by weight.
  • Commercially available organic UV absorbers according to the invention are, for example, Tinuvin 479 (BASF), Tinuvin 400 (BASF), Tinuvin 328 (BASF), Tinuvin 384-2 (BASF), Tinuvin 982 (BASF) and Tinuvin 1130 (BASF).
  • the inorganic UV absorber is selected from the group consisting of nanoparticles of T1O 2 , ZrÜ 2 , ZnO, CeÜ 2 and mixtures thereof.
  • ZnO and CeO 2 are particularly preferred since they avoid a photocatalytic effect which can lead to damage to the embossing lacquer.
  • inorganic UV absorbers and in particular UV-absorbing inorganic nanoparticles offers the advantage that they have a greater UV stability and thus a longer service life.
  • such nanoparticles also have a comparatively higher long-term stability compared with the organic UV absorbers, such as benzotriazoles and phenyltriazines.
  • non-UV-active nanoparticles for example silica nanoparticles, they can also increase the scratch resistance and abrasion resistance on account of their hardness.
  • the proportion of UV absorber in the embossing lacquer composition is preferred for the proportion of UV absorber in the embossing lacquer composition to be from 0.9 to 5% by weight, more preferably about 1% by weight.
  • system further comprises at least one radical scavenger.
  • the radical scavenger is a HALS (hindered amine light stabilizer / hindered amine light stabilizer).
  • the HALS is selected from the group consisting of bis (1, 2, 2, 6, 6 pentamethyl-4-piperidyl) sebacate, methyl (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethyl) piperidinyl) sebacate, 2,4-bis [N-butyl- [1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) amino] -6- (2-hydroxyethylamine) -1, 3, 4-triazine and mixtures thereof.
  • HALS are preferably used in a molar proportion of about 1 .-% ⁇ be set.
  • Commercially available HALS invention are at ⁇ play as Tinuvin 292 (BASF), CHISORB 292 (Double Bond Chemical Ind., Co., Ltd.), Tinuvin 123 (BASF) and Tinuvin 152 (BASF).
  • the proportion of Radikalfän ⁇ ger in the embossing lacquer composition from 0.9 to 5 wt .-%, more preferably about 1 wt .-%, is.
  • the at least one photoinitiator is selected from the group consisting of (alkyl) -benzoyl-phenyl-phosphine oxides, 1-hydroxyalkylphenyl ketones, 2, 2-dimethoxy-l, 2-diphenylethane-1-one, thioxanthones, ketosulfones and mixtures thereof, more preferably from (alkyl) benzoyl-phenyl-phosphine oxides, 1-hydroxyalkyl phenyl ketones, and mixtures thereof.
  • TPO-L ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate
  • diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide bis (2,6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide, 1-hydroxycyclohexyl phenyl ketone, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide (BAPO) and mixtures thereof.
  • the photoinitiators are preferably used in a mole fraction of about 3 wt .-%.
  • Commercially available photoinitiators according to the invention are, for example, luciferin (Irgacure) or omnirad TPO-L (BASF or IGM), Genocure TPO (Rahn), Genocure LTM
  • the further constituent ⁇ parts of the prepolymer are independently selected from: i) at least one cross-linkable oligomer and / or polymer compound, ii) at least one monomer as reactive diluent, iii) at least one thiol-containing monomer, and iv) at least one Non-stick additive.
  • the monomers, oligomers and / or polymers used in the prepolymer composition are preferably UV-curable.
  • the at least one crosslinkable oligomer and / or polymer compound of the prepolymer composition is selected from the group consisting of urethane acrylates, polyacrylates, polymethacrylates, epoxyacrylates, silicone acrylates, polyester acrylates, polyether acrylates and mixtures thereof.
  • the at least one crosslinkable oligomer and / or polymer compound is a urethane-acrylate oligomer.
  • the at least one crosslinkable oligomer and / or polymer compound is a photocrosslinkable.
  • Commercially available OF INVENTION ⁇ dung modern urethane-acrylate oligomers are, for example, Ebecryl 8402, Ebecryl 4858, Ebecryl 4680, Genomer 4316, Miramer PU2100 and 2200th It is particularly preferred according to the invention for the at least one crosslinkable oligomer and / or polymer compound to be present in the prepolymer composition in a total amount of from 1 to 60% by weight.
  • the at least one monomer as reac ⁇ tivver Plantner selected from the group consisting of acrylates and methacrylates.
  • the at least one monomer is hexanediol diacrylate (HDDA), cyclohexyl acrylate, norbornyl acrylate, 2-ethylhexyl acrylate or trimethylolpropane triacrylate (TMPTA).
  • HDDA hexanediol diacrylate
  • TMPTA trimethylolpropane triacrylate
  • the at least one oligomer and / or polymer compound and / or the thiol-containing monomer comprises at least two functional groups (bifunk ⁇ tional), particularly preferably more than two functional groups Grup ⁇ (multi-functional) that.
  • Suitable weather-stable urethane-acrylate oligomers and suitable monomers as reactive diluents preferably have as few (poly) ether and (poly) ester groups as possible. Through these groups, the UV and hydrolysis of the embossing ⁇ paints and microstructured surfaces are increased.
  • the thiol-containing monomer may have at least two thiol groups and / o ⁇ selected from the group consisting of 3-mercaptopropionic pionaten, 2-Mercaptoacetaten, len thioglycolates and alkyldithio.
  • the thiol-containing monomer is trimethylolpropane trimercaptopropionate (TMPMP), glycol dimer captopropionate (GDMP), pentaerythritol tetra (3-mercaptopropionate) (PETMP) or tris [2- (3-mercaptopropionyloxy) ethyl] isocyanurate (TEMPIC).
  • Preferred non-stick additives are selected from the group consisting of alkyl (meth) acrylates, poly-siloxane (meth) acrylates, perfluoroalkyl (meth) acrylates, perfluoropolyether (meth) acrylates, alkyl vinyl ethers, Poly-siloxane vinyl ethers, perfluoroalkyl vinyl ethers and perfluoropolyether vinyl ethers.
  • the invention has the advantage that the UV stability of the (UV) IL embossing lacquer is significantly increased by the addition of UV absorber and optionally radical scavenger, already in proportions of about 1% by weight each.
  • embossing lacquer composition according to the invention for riblet structures based on a prepolymer composition comprising the system of UV absorber and photoinitiator, with appropriate matching of the absorption spectra of the components, enables a high UV polymerization and thus R2R UV-NIL prep speed, with excellent UV stabilization and a yellowing not perceptible to the naked eye.
  • R2R-UV-NIL weather and abrasion resistant micro- and nanostructured surfaces for exterior applications can be obtained by means of R2R-UV-NIL.
  • the invention further relates to a microstructured surface, preferably with a riblet structure, which is obtained starting from the embossing lacquer composition according to the invention.
  • Microstructured surfaces have a structure or topography with elevations or depressions whose spacing from each other and depth or height in the sub-millimeter range. Preferably, the distance from one another and the depth are in the range of 0.5 to 100 ⁇ m, more preferably 0.5 to 60 ⁇ m.
  • a before ⁇ ferred microstructured surface is within the scope of the inventions preferably dung a surface with riblet structure.
  • a riblet designates a surface geometry which causes a reduction of the frictional resistance to surfaces turbulently overflowed in a certain flow direction.
  • the invention is also a aircraft component with the inventive microstructured surface, before ⁇ preferably with Riblet structure.
  • FIGS. 3 to 6 show examples of photoinitiator according to the invention and corresponding absorption spectra.
  • Figure 7 Comparative Examples of photoinitiators and ent ⁇ speaking absorption spectra.
  • FIG. 8 a comparison of absorption spectra of different
  • FIG. 1 shows examples of organic UV absorbers according to the invention and their absorption spectra.
  • the organic UV absorbers are substituted 2-hydroxyphenyltriazines, which are commercially available under the trade names Tinuvin 479 and Tinuvin 400.
  • Figure 2 shows examples of the invention of HALS as radical catcher ⁇ .
  • HALS radical catcher ⁇ .
  • a mixture of bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate and methyl (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate (Tinuvin 292, CHISORB 292) and, on the other hand, the compound bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl) sebacate (Tinuvin 123).
  • FIGS. 3 to 6 depict examples of photoinitiators according to the invention and corresponding absorption spectra.
  • 3 shows the compound ethyl (2, 4, 6-trimethylbenzoyl) phenylphosphinate (TPO-L), which is an (alkyl) benzoyl-phenyl-phosphine oxide.
  • the photoinitiator used is particularly preferably 3% by weight of luciferin (Irgacure) TPO-L (BASF). This is set an ⁇ in the form of a liquid and is readily miscible.
  • 4 shows the connection of diphenyl (2, 4, 6-trimethylbenzoyl) phosphine oxide (Genocure TPO) ready to be inserted ⁇ is in the form of a crystalline solid.
  • FIG. 5 shows the absorption spectrum for a photoinitiator mixture of bis (2, 6-dimethoxybenzoyl) -2,4,9-trimethylpentylphosphine oxide and 1-hydroxycyclohexylphenylketone. This mixture is commercially available under the name Genocure LTM. The mixture shows good absorption in the range between 350 and 400 nm.
  • Genocure LTM Genocure LTM
  • FIG. 7 shows two comparative examples of photoinitiators and corresponding absorption spectra. It han ⁇ punched by the compounds 2, 4-Diethyltioxanthon (Genocure DETX) and isopropyl-thioxanthone (ITX Genocure). The two photoinitiators absorbing in a longer wavelength range lead to a yellowing of the embossing lacquer.
  • FIG. 8 shows a comparison of the absorption spectra of various photoinitiators according to the invention and not according to the invention.
  • the strong absorption of the UV absorber (Tinuvin 479) leads to a prevention of the UV curing of the prepolymerization composition (or of the embossing lacquer). This can be avoided by choosing a suitable photoinitiator with absorption in the long wavelength range.
  • the absorption of the photoinitiator is too long-wavelength (greater than 400 nm), this can lead to yellowing of the embossing lacquer. This occurs, for example, for the photoinitiator BAPO (Irgure 819). Therefore, a combination of the photoinitiator TPO-L with the UV absorber Tinuvin 479 is preferably used.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Aviation & Aerospace Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Polymerisation Methods In General (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de peinture pour impression en relief servant à la réalisation de « riblets », à base d'une composition prépolymère qui comprend un système composé : a) d'au moins un photoamorceur présentant une bande d'absorption dans le domaine UV lointain et b) d'au moins un absorbeur d'UV.
PCT/EP2018/052747 2017-02-08 2018-02-05 Composition de peinture pour impression en relief, surface microstructurée réalisée à partir de celle-ci et élément d'avion comportant une telle surface microstructurée Ceased WO2018146031A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP18707629.4A EP3580611A1 (fr) 2017-02-08 2018-02-05 Composition de peinture pour impression en relief, surface microstructurée réalisée à partir de celle-ci et élément d'avion comportant une telle surface microstructurée

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102017201991.3 2017-02-08
DE102017201991.3A DE102017201991A1 (de) 2017-02-08 2017-02-08 Prägelackzusammensetzung, daraus hergestellte mikrostrukturierte Oberfläche und Flugzeugbauteil mit einer solchen mikrostrukturierten Oberfläche

Publications (1)

Publication Number Publication Date
WO2018146031A1 true WO2018146031A1 (fr) 2018-08-16

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EP (1) EP3580611A1 (fr)
DE (1) DE102017201991A1 (fr)
WO (1) WO2018146031A1 (fr)

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WO2016090395A1 (fr) 2014-12-10 2016-06-16 Joanneum Research Forschungsgesellschaft Mbh Composition polymère ou prépolymère ou peinture d'impression en relief comprenant une telle composition et son utilisation

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Publication number Publication date
EP3580611A1 (fr) 2019-12-18
DE102017201991A1 (de) 2018-08-09

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