WO2022200192A1 - Revêtement de surface incolore - Google Patents

Revêtement de surface incolore Download PDF

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Publication number
WO2022200192A1
WO2022200192A1 PCT/EP2022/057092 EP2022057092W WO2022200192A1 WO 2022200192 A1 WO2022200192 A1 WO 2022200192A1 EP 2022057092 W EP2022057092 W EP 2022057092W WO 2022200192 A1 WO2022200192 A1 WO 2022200192A1
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Prior art keywords
coated
nir
vis
use according
radical
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PCT/EP2022/057092
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German (de)
English (en)
Inventor
Lukas Appelhoff
Qunying WANG
Bernd Strehmel
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Hochschule Niederrhein
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Publication of WO2022200192A1 publication Critical patent/WO2022200192A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0209—Multistage baking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0254—After-treatment
    • B05D3/0263—After-treatment with IR heaters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
    • B05D3/065—After-treatment
    • B05D3/067—Curing or cross-linking the coating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2270/00—Compositions for creating interpenetrating networks

Definitions

  • the invention is in the field of lacquers and paints and relates to surface coatings based on aqueous dispersions with polymeric binders, which are characterized in that they are colorless to the human eye after drying/filming and crosslinking.
  • Lacquers and paints are by far the most important means of coating surfaces. In addition to aesthetic aspects, protective functions, in particular protection against corrosion, are paramount. More than 30 billion tons of coatings are produced worldwide every year, more than half of which are used in the construction industry, followed by industrial and powder coatings.
  • the surface coating with lacquers or paints is based on the fact that an aqueous dispersion is applied with a binder, which then dries and forms a film through polymerization.
  • the drying usually takes place physically, i.e. the water is evaporated in an oven and the dry film remains.
  • such a process is time-consuming and requires the supply of energy from the outside.
  • FEW CHEMICALS relates to cyanine dyes containing sulfo-aryl and N-sulfo-alkyl groups or trialkylammonium-alkyl groups, where the alkyl group has 1-4 carbon atoms and a bridged five- or six-membered ring structure
  • Methine group containing a differently substituted pyrimidinetrione in its meso position with a reactive group which enables binding to carrier substances, with at least one oxygen atom, preferably an oxygen atom in the para-position to the bond to the methine chain, in the pyrimidinetrione optionally by a sulfur atom is substituted is new.
  • WO 2012 063964 A1 (HAYASHIBARA) describes a new near infrared absorbing cyanine pigment, namely a benzo[c,d]indolium heptamethine cyanine pigment.
  • WO 2014078 140 A1 discloses a negative working lithographic printing plate precursor used for making lithographic printing plates from infrared radiation images.
  • the precursor comprises a free radical source and a specific cyanine dye as an infrared radiation absorber.
  • US 6,140,384 A relates to a photopolymerizable composition
  • a photopolymerizable composition comprising i) an addition polymerizable compound having an ethylenically unsaturated double bond, ii) a sensitizing dye and iii) a titanocene compound.
  • JP 2002 189291 A1 relates to a photopolymerizable composition containing (A) an ethylenically unsaturated compound, (B) a sensitizer and (C) a photopolymerization initiator, the sensitizer being a cyanine compound having a tetrazolyloxy group or a tetrazolylthio group on a heptamethine chain.
  • JP 2014 172333 A discloses a resin composition for laser engraving, comprising a binder polymer containing ethylenically unsaturated groups; and a compound containing tertiary ester groups and ethylenically unsaturated groups.
  • US Pat. No. 10,767,064 B2 (AGFA) relates to an ink for an inkjet printer containing water, a water-soluble organic solvent, a resin and an anionic heptamethine cyanine dye which contains a substituted or unsubstituted five- or six-membered ring in the heptamethine chain, where the dye has an absorption maximum between 800 and 1200 nm to increase drying speed and improve image quality when dried with NIR or CIR dryers.
  • J. Coat Technol Res 16, pp. 1527-1541 discloses the use of LEDs that emit NIR radiation for drying or filming of paint layers and as a replacement for the previously known oven processes.
  • the object of the present invention was therefore to provide colorless surface coatings, be they lacquers or paints, based on aqueous dispersions which are colorless and almost water-free after photonic drying and curing.
  • the invention relates to a colorless surface coating which can be obtained or obtained by:
  • At least one NIR absorber at least one NIR absorber, and (d) contain at least one radical-forming UV-VIS photoinitiator or system.
  • Polymeric binders in the dispersions are preferably reaction products of di- and tri-isocyanate compounds with hydroxyl compounds, which form a polyurethane film after application to the surfaces and drying.
  • the isocyanate and the hydroxyl components can be added individually to the dispersion, but it is also possible to use a precondensate of the two substances.
  • isocyanate compounds can be of aliphatic origin, such as hexamethylene diisocyanate, the preferred embodiments include aromatic or cycloaliphatic compounds. Particular preference is given to toluylene diisocyanate, as is available on the market under the brand name Desmodur®, for example. In view of the performance of the final product, a tolylene diisocyanate comprising about 50 to about 80 mol% of the 2,4-isomer is particularly preferred. 2,4,6-Toluene-triyl triisocyanate or triphenylmethane-4,4',4"-triisocyanate can be used as higher-functional isocyanates:
  • Isophorone diisocyanate can also be considered as a cycloaliphatic alternative.
  • Particularly suitable hydroxyl compounds are polyethers, specifically polyethylene and polypropylene glycol ethers with molecular weights in the range from 150 to 1500, which can also be end-capped with methyl or butyl functions at one end.
  • PEG300, PEG500, PEG1000, MPEG300, MPEG350, MPEG1000, BPEG300 or BPEG350 are particularly suitable.
  • the isocyanates and the hydroxyl compounds are used in a molar ratio of about 1:1 to about 1:5 and in particular about 1.2 to about 1:3.
  • other aqueous dispersions are suitable for this invention, the z. B. based on (meth) acrylic compounds are constructed. These can be built up from one or more (meth)acrylic acid derivatives and other vinyl derivatives which polymerize free-radically.
  • All compounds which polymerize according to the mechanism of free radical polymerization and crosslink with a functionality >2 can be used as free-radically polymerizable crosslinking agents (component b).
  • These include, in particular, acrylic acid and/or methacrylic acid derivatives and esters derived therefrom, such as 1,6-hexanediol diarylate, trimethylolpropane triacrylate, urethane dimethacrylate, or else tri(propylene glycol) diacrylate, with mixtures of several crosslinking monomers also being able to be used.
  • the following monomers M1-M4 represent some of the other numerous alternatives.
  • additives can be added as needed to improve the dispersibility of the monomer(s) in the aqueous dispersion.
  • polymethines polymethine dyes
  • cyanine dyes Physicai Sciences Reviews 2020, 20190145
  • Heptamethine structure selected. These ideally absorb in a spectral range of 700- 1500 nm.
  • Compounds A1 -A16 represent just a few of the many possible structures.
  • Photoinitiators (component d) used are preferably those which, after Norrish Type I cleavage with a UV/VIS LED, form initiating radicals for a free-radical polymerization.
  • Photoinitiators are shown in "Photoinitiators for Polymer Synthesis", Wiley-VCH, Weinheim, 2012 or “Industrial Photoinitiators: A Technical Guide", CRC Press, Boca Raton, 2010, among others. In principle, therefore, all substances that form free radicals and absorb light in the range from 350 to 450 nm are suitable.
  • the structures PI1 to PI3 are named as representative of this.
  • type II initiators are also suitable which contain, among other things, derivatives of thioxanthone as a light-absorbing component and a coinitiator.
  • Camphorquinone can also be used.
  • Possible coinitiators are onium salts such as iodonium or sulfonium salts, or amines such as DABCO or dimethylamino(ethyl benzoate).
  • the coating dispersions according to the invention must contain a polymeric binder (either a mixture of isocyanate and hydroxyl compound or a precondensate made therefrom) and a crosslinking agent.
  • An NIR absorber must also be present for the first step of photonic drying and a UV photoinitiator for curing.
  • the dispersions can also contain free-radical initiators such as hydrazine, solvents, namely water, and pH regulators.
  • a typical dispersion according to the present invention has the following composition (all data as % by weight):
  • the paint dispersion can also be prepared in stages, for example by preparing an aqueous predispersion of binder and free-radical initiator, adjusting the pH and only then adding the other components, ie crosslinking agent, absorber and photoinitiator.
  • the photonic drying can preferably be carried out using semiconductor light sources such as LEDs or lasers, provided these have the required emission in the range from 700 to 1,200 nm. Large-area LEDs with emissions at 800 to 870 nm, 920 to 950 nm and 950 to 1050 nm are particularly preferred.
  • semiconductor light sources such as LEDs or lasers
  • Large-area LEDs with emissions at 800 to 870 nm, 920 to 950 nm and 950 to 1050 nm are particularly preferred.
  • the physical drying takes place with an NIR light source, whereby the generation of heat, which is required for the physical drying of the coating material, is coupled to a photonic process. After light absorption has taken place, the lower vibrational modes of the excited state are coupled with higher vibrational modes of the ground state. The efficiency of this process is >75% and is referred to in the professional world as internal conversion. The release of excess energy from higher modes of the ground state occurs through collisions with matrix molecules.
  • UV-VIS light sources Conventional medium-pressure mercury lamps or semiconductor light sources such as LEDs can be used as UV-VIS light sources, provided there is an emission in the range from 350 to 450 nm.
  • large-area LEDs are preferred which emit at 350-370 nm, 380-395 nm, 400-420 nm and 440-470 nm.
  • Another subject of the invention relates to the use of aqueous dispersions containing
  • At least one radical-forming UV-VIS photoinitiator for producing colorless surface coatings are used in the furniture industry, the packaging industry, the graphics industry with a focus on printed matter, the textile industry, the construction industry - to name just a few areas of possible commercial use.
  • the surfaces to be coated can be selected from the group formed by wood, stone, ceramics, glass, paper, cardboard, metal, textile surfaces and textile fibers as well as medical and orthopedic hard surfaces such as teeth or implants.
  • the surfaces to be coated can be selected from the group formed by wood, stone, ceramics, glass, paper, cardboard, metal, textile surfaces and textile fibers as well as medical and orthopedic hard surfaces such as teeth or implants.
  • the polyurethane dispersion used was created according to the following recipe.
  • the polyether (Voranol 101 OL) was used unchanged by Dow Chemicals. Other chemicals used in the synthesis were: dimethylolpropionic acid (2,2-bis(hydroxymethyl)propionic acid), isophorone diisocyanate, triethylamine, and hydrazine hydrate.
  • the compounds from items 1-3 in the above table were placed in the reaction flask and slowly heated to 90° C. with stirring. The isocyanate content was determined after about 60 minutes. As soon as this was below 8.9%, it was cooled to 60.degree. The compound in position 4 is carefully added dropwise and the heating is removed from the reaction solution. The water (position 5) was then rapidly added dropwise with vigorous stirring, so that an emulsion without phase separation was formed.
  • the coating obtained in this way was then treated with an NIR source, which is suitably an NIR LED with emission at 805 nm or 860 nm or NIR laser with line focus with emission at 980 nm (length of the laser line: 2 cm, width of the laser line: 1 mm). exposed.
  • the applied solution filmed and was then exposed to a UV LED.
  • the colored coating filmed with an NIR source lost its color and was colorless and crosslinked after UV exposure. The glass transition temperature had increased for these semi-interpenetrating networks, indicating a reaction of the monomer.
  • These films were characterized using dynamic mechanical analysis. The results are summarized in Table 2.
  • the coatings applied in this way were not tacky after the second exposure step and had a clear, colorless appearance. According to FTIR investigations, the cured films were practically free of water.
  • Figures 1 to 4 show selected graphs of the storage modulus of the examined systems of Examples 3 to 6, which were recorded with dynamic mechanical analysis (DMA).
  • Figure 5 shows the films which, following the above procedure, were first irradiated with an NIR source and then with a UV LED, yielding a transparent, clear, colorless film.
  • the coating solution described in example 1 was applied to different surfaces under the conditions described in example 2.
  • the procedure is such that the amount that was applied to achieve the described layer thickness of a glass substrate was 1.5 times the amount.
  • the substrates described in Table 3 were not transparent.
  • An NIR LED with emission at 860 nm and UV LED m emission at 395 nm under the conditions specified in Example 2 was used as the NIR source. The following results were obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Paints Or Removers (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention concerne un revêtement de surface incolore obtenu par la mise en contact d'une surface à revêtir avec une dispersion aqueuse de peinture, puis le séchage et le recouvrement de la surface ainsi traitée avec un film à l'aide d'un rayonnement NIR, puis la réticulation du film séché au moyen d'un rayonnement UV-VIS.
PCT/EP2022/057092 2021-03-22 2022-03-17 Revêtement de surface incolore WO2022200192A1 (fr)

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DE102021106964.5 2021-03-22
DE102021106964.5A DE102021106964A1 (de) 2021-03-22 2021-03-22 Farblose oberflächenbeschichtung

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024070694A1 (fr) * 2022-09-26 2024-04-04 富士フイルム株式会社 Composition, film, filtre optique, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, capteur infrarouge, module caméra et composé

Citations (10)

* Cited by examiner, † Cited by third party
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DE4331162A1 (de) 1993-09-14 1995-03-16 Bayer Ag Verfahren zur Herstellung von Cyaninfarbstoffen
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