EP1960449A2 - Melanges liquides, thermodurcissables, procede de production et d'utilisation associes - Google Patents

Melanges liquides, thermodurcissables, procede de production et d'utilisation associes

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Publication number
EP1960449A2
EP1960449A2 EP06819015A EP06819015A EP1960449A2 EP 1960449 A2 EP1960449 A2 EP 1960449A2 EP 06819015 A EP06819015 A EP 06819015A EP 06819015 A EP06819015 A EP 06819015A EP 1960449 A2 EP1960449 A2 EP 1960449A2
Authority
EP
European Patent Office
Prior art keywords
liquid
mixtures according
thermally
groups
compounds
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.)
Withdrawn
Application number
EP06819015A
Other languages
German (de)
English (en)
Inventor
Andreas Poppe
Elke Westhoff
Simone Hesener
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.)
BASF Coatings GmbH
Original Assignee
BASF Coatings 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 BASF Coatings GmbH filed Critical BASF Coatings GmbH
Publication of EP1960449A2 publication Critical patent/EP1960449A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
    • 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
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
    • 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

Definitions

  • the present invention relates to new, liquid, thermally hardenable mixtures.
  • the present invention relates to a new process for producing liquid, thermally hardenable mixtures.
  • the present invention relates to the use of the new, liquid, thermally hardenable mixtures and to those prepared by the new process. liquid, thermally hardenable mixtures
  • Thermally curable mixtures in particular coating materials, especially clear lacquers, which contain compounds selected from the group consisting of cyclic and cyclic C 9 -C 16 -alkanes which are functionalized with at least two hydroxyl or at least one hydroxyl and at least one thiol group, are known from German patent applications DE 198 09 643 A1 and DE 199 40 855 A1.
  • the known thermally hardenable coating materials necessarily contain at least one polymeric binder.
  • DE 199 38 758 A1 in Example 1 describes the preparation of a polyester which is used as a polymeric binder in Clear lacquer coating materials are used
  • the known coating materials it is necessary to add comparatively large amounts of organic solvents to them.
  • the compounds as reactive thinners bring about an improvement in this regard because the viscosity of the known ones Coating materials compared to the viscosity of the coating materials free of these compounds is significantly lower, however, this effect is not sufficient to provide manageable, in particular applicable, thermally hardenable mixtures, in particular coating materials, especially clearcoats, which have a solids content during application> 80 wt -% to have
  • the object of the present invention was to provide new, liquid, thermally hardenable mixtures which, even with a film-forming solid of up to 100% by weight, have a low viscosity, so that they can be processed and handled, in particular applied, without problems
  • the new, liquid, thermally hardenable mixtures are said to be outstandingly suitable for the production of new thermosetting materials
  • the new coating materials in particular are said to be excellent as primers, primers, fillers, basecoats, solid-color topcoats and clearcoats for the production of new single- or multi-layer polymer coatings, corrosion protection layers,
  • Solid top coats and clear coats can be used. Above all, however, the new clear coats should be excellent for the production of new, single or multi-layer clear coats in the context of new, color and / or effect multi-coat coats, in particular of new multi-coat coats that are wet-in-wet -Procedures to be produced, suitable
  • the new clearcoats should have a very good flow, a high gloss, a low haze, a high level of image differentiation (DOI), as well as a high chemical resistance, condensation resistance, weather resistance and scratch resistance. They should also be free of paint defects such as specks , Craters, stoves, pinpricks and pimples
  • the new, liquid, thermally hardenable mixtures which (A) have at least one low molecular weight polyol with at least three hydroxyl groups and a hydroxyl group content corresponding to a theoretical OH number of 800 to 1 900 mg KOH / g,
  • (B) at least one compound selected from the group consisting of the cyclic and cyclic C 9 -C 16 alkanes which are functionalized with at least two hydroxyl or at least one hydroxyl and at least one thiol group, and (C) contain at least one low molecular weight or ohomeric compound with at least two reactive functional groups (d) which are complementary to hydroxyl groups and thiol groups and which are referred to below as “mixtures according to the invention”
  • thermosetting materials had a low viscosity even with a film-forming solid of up to 100% by weight, so that they could be processed and handled without problems, in particular applied
  • the mixtures according to the invention were outstandingly suitable for the production of new thermosetting materials
  • the coating materials of the invention were excellent as new primers, primers, fillers, basecoats, solid-color topcoats and clearcoats for the production of new, single- or multi-layer primer coatings, corrosion protection layers,
  • Solid-color top coats and clear coats are used. Above all, however, the clear coats according to the invention were outstanding for the production of new, single- or multi-layer clear coats in the context of new, color and / or effect-giving multi-layer coats, in particular new multi-coat coats using the wet-on-wet method be produced, suitable
  • the clearcoats according to the invention had a very good flow, a high gloss, a low haze, a high level of distinctness of image (DOI), as well as a high chemical resistance, condensation resistance, weather resistance and scratch resistance. They were also free from paint defects such as cloudiness, light Dark shades (clouds), specks, craters, stoves, pinpricks and pimples
  • low molecular weight means that the compounds in question have a number average molecular weight ⁇ 1,500 daltons
  • Ohgomeric means that the compounds in question are composed of 3 to 10 low molecular weight structural units. They preferably have a number average molecular weight of 500 to 10,000 daltons, preferably 1,000 to 5,000 daltons and in particular 1,500 to 4,500 daltons
  • Polymer means that the compounds in question are composed of more than 10 low molecular weight structural units. They preferably have a number average Molecular weight of 1,000 to 100,000 daltons, preferably 1,500 to 50,000 daltons and in particular 2,000 to 20,000 daltons
  • the film-forming solid is the sum of all the components of a thermally hardenable mixture that form the thermosetting material when hardened
  • the first essential component of the mixture according to the invention is at least one, in particular one, low molecular weight polyol (A) with at least three, in particular three, hydroxyl groups and a hydroxyl group content corresponding to a theoretical OH number of 800 to 1 900 mg KOH / g
  • Suitable polyols (A) are all polyols which have this property profile
  • the polyol (A) is preferably selected from the group consisting of tylenes, tetrols, pentites and hexites
  • the polyol (A) is preferably selected from the group consisting of t ⁇ methylolmethane, trimethylolethane, t ⁇ methylolpropane, glycerin, erythnt, threit, pentaerythritol, dipentaerythnt, homopentaerythnt, arabit, adonit, xylitol, mannitol, sorbitol, dulcitol and inositol
  • Trimethylolpropane in particular is used
  • the content of compound (A) in the mixture according to the invention can vary widely and can therefore be adapted excellently to the requirements of the individual case.
  • the content is preferably 1 to 30% by weight, preferably 2 to 25% by weight and in particular 3 to 20% by weight. , each based on the film-forming solid of the mixture according to the invention
  • the second essential constituent of the mixture according to the invention is at least one compound (B) which is preferably selected from the group consisting of cyclic and acyclic C 9 -C 16 alkanes which have at least two hydroxyl or at least one hydroxyl and at least one thiol group are functionalized with at least two hydroxyl groups, in particular with two hydroxyl groups.
  • the Cg-C 16 alkanes from which the compounds (B) are derived are basically all linear and branched, preferably branched, alkanes having 9 to 16 carbon atoms
  • the C 9 -C 16 alkanes from which the compounds (B) are derived are preferably selected from the group consisting of 2-methyloctane, 4-methyloctane, 2,3-dimethylheptane, 3,4-dimethylheptane , 2,6-dimethyl-heptane, 3,5-dimethyl-heptane, 2-methyl-4-ethyl-hexane, isopropyl-cyclohexane, 4-ethyl-octane, 2,3,4,5-tetramethyl-hexane, 2,3 -D ⁇ ethyl-hexane 1-methyl-2-n-propyl-cyclohexane, 2,4,5,6-tetramethyl-heptane, 3-methyl-6-ethyl-oct
  • the C 9 -C 16 alkanes are preferably positionally isomeric diethyloctanes
  • Preferred compounds (B) are accordingly the positionally isomeric diethyloctanediols, particularly preferably those which contain linear C 8 carbon chains
  • the C 8 carbon chain with respect to the two ethyl groups can have the substitution pattern 2,3, 2,4, 2,5, 2,6, 2,7, 3,4, 3,5, 3,6 or 4,5
  • the C 8 carbon chain with respect to the two hydroxyl groups can have the substitution pattern 1, 2, 1, 3, 1, 4, 1, 5, 1, 6, 1, 7, 1, 8, 2,3, 2,4, 2 , 5, 2.6, 2.7, 2.8, 3.4, 3.5, 3.6, 3.7, 3.8, 4.5, 4.6, 4.8, 5.6 , 5.7, 5.8, 6.7, 6.8 or 7.8
  • the diethyloctanediols (B) are preferably selected from the group consisting of 2,3-dimethyloctane-1, 2-, -1, 3-, -1, 4-, -1, 5-, -1, 6-, -1 J-, -1, 8-, -2.3-, -2.4-, -2.5 -, -2.6-, -2.7-, -2.8-, -3.4- , -3.5-, -3.6-, -3.7-, -3.8 -, -4.5-, -4.6-, -4.7-, -4.8-, - 5.6 -, -5.7-, -5.8-, -6.7-, -6.8- and - 7.8-diol,
  • the two ethyl groups are preferably in the 2,4-position.
  • the two hydroxyl groups are preferably in the 1,5-position
  • the positionally isomeric diethyloctanediols (B) are compounds known per se and can be prepared by customary and known synthetic methods in organic chemistry, such as base-catalyzed aldol condensation, or they are obtained as by-products of large-scale chemical syntheses, such as the preparation of 2-ethylhexanol
  • the content of compounds (B) in the mixture according to the invention can vary widely and can therefore be adapted excellently to the requirements of the individual case.
  • the content is preferably 2 to 60% by weight, preferably 5 to 50% by weight and in particular 10 to 40% by weight. %, each based on the film-forming solid of the mixture according to the invention
  • the third essential component of the mixture according to the invention is at least one compound (C). At least two, in particular two, compounds (C) are preferably used
  • the compound (C) is low molecular weight or oligomeric and contains at least two, in particular at least three, reactive functional groups (d) which are complementary to hydroxyl groups and thiol groups, in particular hydroxyl groups.
  • the complementary reactive functional groups (d) are preferably selected from the group consisting of carboxyl -, anhydride, epoxy, blocked and unblocked isocyanate, urethane, methylol, methylol ether, silane, carbonate and beta-hydroxyalkylamide groups, the groups (c1) from the group consisting of blocked and unblocked isocyanate groups, urethane groups, methylol groups and methylol ether groups
  • the compounds (C) are particularly preferably selected from the group consisting of blocked and unblocked polyisocyanates and amino resins
  • the very particularly preferred compounds (C) are customary and known crosslinking agents (C), as described, for example, in German patent application DE 198 09 643 A1, page 5, line 17 to page 6, line 61, or the German one Patent application DE 199 40 855 A1, column 24, line 33, until column 27, line 24, are known
  • the content of the compounds (C) in the mixture according to the invention can also vary very widely, so that it can be adapted excellently to the requirements of the individual case.
  • the content is preferably 10 to 90% by weight, preferably 15 to 85% by weight and in particular 20 to 80% by weight, based in each case on the film-forming solid of the mixture according to the invention.
  • Thiol groups in the compounds (B) to the complementary reactive functional groups (c1) in the compounds (C) can vary very widely, so that it can be adapted excellently to the requirements of the individual case.
  • the equivalent ratio is preferably 1: 3 to 3: 1, preferably 1: 2.5 to 2.5: 1, particularly preferably 1: 2 to 2: 1, very particularly preferably 1: 1.5 to 1.5: 1 and in particular 1: 1, 2 to 1, 2: 1.
  • additives (D) which also contain hydroxyl groups and / or thiol groups are used, these groups are taken into account when setting the equivalent ratio, so that this preferably remains within the preferred ranges described above.
  • the mixture according to the invention can also contain at least one additive (D).
  • Additives (D) are all substances which are customarily used in the field of coating materials, adhesives and sealing compounds and the precursors of molded parts and films, in particular in the field of coating materials.
  • the additive (D) is preferably selected from the group consisting of physically, thermally and / or polymeric and oligomeric binders curable with actinic radiation; organic and inorganic solvents; residue-free or essentially residue-free thermally decomposable salts; Neutralizing agents; from the compounds (A) and (B) different, thermally curable reactive diluents; reactive diluents curable with actinic radiation; opaque and transparent, color and / or effect pigments; molecularly dispersible dyes; opaque and transparent fillers; Nanoparticles; Light stabilizers; Antioxidants; Deaerators; Wetting agents; Emulsifiers; Defoaming; Slip additives; Thermal crosslinking catalysts; Polymerization inhibitors; thermolabile free radical initiators; Photoinitiators; Adhesion promoters; Leveling agents; Rheology aids; Flame retardants; Corrosion inhibitors; Adhesion promoters; Flow aids; To grow; Desiccants;
  • thermosetting materials according to the invention which have excellent performance properties.
  • the mixtures according to the invention are used for the production of transparent, in particular clear, thermosetting materials according to the invention, they contain no opaque additives (D).
  • the content of the additives (D) in the mixture according to the invention can vary widely, so that it can be optimally adapted to the particular intended use.
  • the additives (D) are preferably used in the customary and known, effective amounts. These are familiar to the person skilled in the art on the basis of his general specialist knowledge, the information in the aforementioned German patent applications being able to serve as a guideline.
  • the film-forming solid contained in the mixture according to the invention can vary widely and can therefore be adapted excellently to the requirements of the respective intended use.It is a very particular advantage of the mixture according to the invention that it can have a particularly high content of film-forming solid.
  • the film-forming solid is preferably 30 to 100% by weight, preferably 35 to 100% by weight and in particular 40 to 100% by weight, in each case based on the mixture according to the invention
  • the mixtures according to the invention are cured thermally
  • the thermal curing can be supported by the curing initiated with actmic radiation.
  • the curing takes place via groups that contain bonds that can be activated with actmic radiation.
  • electromagnetic radiation such as near infrared (NIR) is visible under actmic radiation
  • UV radiation Light, UV radiation, X-rays or gamma radiation, in particular UV radiation, and corpuscular radiation such as electron radiation, alpha radiation, beta radiation or neutron radiation, in particular electron radiation, are to be understood.
  • corpuscular radiation such as electron radiation, alpha radiation, beta radiation or neutron radiation, in particular electron radiation
  • Thermal curing or dual-cure curing can also be supported by physical curing.
  • the term means
  • Physical hardening means the hardening of a layer from a mixture according to the invention by filming, the linkage within the layer being formed by loops of the
  • the mixtures according to the invention can be free of organic solvents and water, i.e. so-called 100% systems. They can be dissolved or dispersed, ie suspended or emulsified systems in organic solvents and / or water.
  • They can be the one-component systems in which the Components (A) and (B) and the compounds (C) are present side by side, or two- or multi-component systems in which the components (A) and (B) on the one hand and the compounds (C) on the other hand are present separately from one another until shortly before application
  • mixtures according to the invention are 100% systems or systems dissolved in organic solvents
  • the mixtures according to the invention are preferably prepared by the process according to the invention by (1) mixing at least one polyol (A) with at least one compound (B), so that a molecularly disperse solution or a finely divided dispersion (I) results, and
  • the wetting agent (D) is added in process step (1)
  • the mixtures according to the invention are used in the context of the use according to the invention to produce the thermoset materials according to the invention
  • the mixtures according to the invention preferably serve as coating materials, adhesives and sealants according to the invention and as precursors according to the invention of molded parts and films, in particular coating materials, the production of coatings, adhesive layers and seals according to the invention and of molded parts and films, in particular coatings.
  • the coating materials of the invention are particularly preferably used as electrocoat materials, primer coats, fillers or stone chip protection primers, basecoats, solid-color top coats and clear coats for the production of electro-dip coatings, primer paints, filler coatings or stone chip protection primers, basecoats, solid color coats and clear coats.
  • These coatings can be single-layer or multi-layer. They are very particularly preferably multi-layered and can include at least two paints, in particular at least one electrocoat, at least one filler or stone chip protection primer, and at least one basecoat and at least one clear coat or at least one solid-color coat.
  • the multilayer coatings particularly preferably comprise at least one basecoat and at least one clearcoat.
  • the clearcoats are the outermost layer of the multi-coat paint system, which essentially determines the overall visual impression (appearance) and protects the color and / or effect base coat systems from mechanical and chemical damage and radiation damage.
  • the clearcoats according to the invention prove to be particularly insensitive to mechanical stress such as tensile, elongation, impact, scratching or abrasion,
  • mixtures according to the invention are applied to customary and known temporary or permanent substrates
  • Customary and known temporary substrates are preferably used for the production of films and molded parts according to the invention, such as metal and plastic bands or hollow bodies made of metal, glass, plastic, wood or ceramic, which can be easily removed without damaging the films and molded parts according to the invention
  • the substrates are preferably land-based means of transportation operated with muscle power, hot air or wind
  • Water or air such as bicycles, trolleys, rowing boats, sailing boats,
  • Hot air balloons, gas balloons or gliders as well as parts thereof,
  • motorized means of transport on land, water or air such as motorcycles, commercial vehicles or motor vehicles, in particular cars, over or
  • stationary floats such as buoys or parts of port facilities
  • Containers such as coils, containers or packaging
  • electrotechnical components such as electronic winding material, for example coils, optical components,
  • white goods such as household appliances, boilers and radiators
  • the films and molded parts according to the invention can also serve as substrates.
  • the substrates are automobile bodies and parts thereof.
  • the mixtures according to the invention or the coatings according to the invention produced therefrom are preferably used for the initial coating of the Automobile bodies (OEM) or the refinishing of first and second coatings according to the invention and not according to the invention.
  • the first coats of the invention in particular those which contain a clearcoat according to the invention, have excellent overcoatability.
  • the refinish coatings according to the invention adhere outstandingly to the first coats of the invention and not according to the invention
  • the application of the mixtures according to the invention has no special features, but can be carried out by all customary and known application methods suitable for the particular mixture, such as, for example, electrocoating, spraying, spraying, knife coating, brushing, pouring, dipping, dripping or rolling applied
  • Wet-on-wet processes and structures can be used for the production of the multi-layer coatings according to the invention, as described, for example, in German patent applications DE 199 30 067 A1, page 15, line 23, to page 16, line 36, or DE 199 40 855 A1, column 30, line 39, to column 31, line 48, and column 32, lines 15 to 29, are known. It is a very significant advantage of the use according to the invention that basically all layers of the multi-layer coating system according to the invention are produced from the mixtures according to the invention
  • the mixtures according to the invention are generally cured after a certain rest period or exhaust time. They can have a duration of 30 s to 2 h, preferably 1 min to 1 h and in particular 1 to 45 min.
  • the rest period is used, for example, for the course and for degassing applied mixtures according to the invention and for the evaporation of volatile constituents such as any Losem present
  • the exhaust air can be accelerated by an increased temperature, which is not yet sufficient for hardening, and / or by a reduced air humidity
  • the applied mixtures according to the invention are thermally cured, for example, using a gaseous, liquid and / or solid, hot medium, such as hot air, heated oil or heated rollers, or by means of microwave radiation, infrared light and / or near infrared light (NIR).
  • the heating is preferably carried out in a convection oven or by irradiation with IR and / or NIR lamps As with actinic curing Radiation, the thermal curing can also be carried out in stages.
  • the thermal curing is advantageously carried out at temperatures from room temperature to 200 ° C.
  • thermal curing of the mixtures according to the invention can also be carried out with the complete or complete exclusion of oxygen
  • oxygen is considered to be largely excluded if its concentration on the surface of the applied mixtures according to the invention is ⁇ 21% by volume, preferably ⁇ 18% by volume, preferably ⁇ 16% by volume, particularly preferably 14% by volume is particularly preferably 10% by volume and in particular ⁇ 6% by volume
  • oxygen is considered to be completely excluded if its surface concentration is below the detection limit of the customary and known detection methods
  • the concentration of oxygen is preferably> 0.001% by volume, particularly preferably> 0.01% by volume, very particularly preferably> 0.1% by volume and in particular> 0.5% by volume.
  • the desired concentrations of oxygen can be set by the measures described in German patent DE 101 30 972 C1, page 6, paragraphs [0047] to [0052] or by the application of foils
  • Curing with actmic radiation can be carried out with the aid of the customary and known devices and methods, such as those described in German patent application DE 198 18 735 A1, column 10, lines 31 to 61, German patent application DE 102 02 565 A1, page 9, Paragraph [0092], to page 10, paragraph [0106], of German patent application DE 103 16 890 A1, page 17, paragraphs [0128] to [0130], in international patent application WO 94/1 1123, page 2, lines 35 , to page 3, line 6, page 3, lines 10 to 15, and page 8, lines 1 to 14, or US Pat. No. 6,743,466 B2, column 6, line 53, to column 7, line 14 will
  • thermosetting materials according to the invention in particular the films, moldings, coatings, adhesive layers and seals according to the invention, are outstandingly suitable for coating, gluing, sealing, wrapping and packaging the substrates described above
  • the resulting substrates according to the invention which are coated with coatings according to the invention, bonded with adhesive layers according to the invention, sealed with a seal according to the invention and / or enveloped or packaged with films and / or moldings according to the invention, have excellent performance properties combined with a particularly long service life
  • the compound (C1) (blocked polyisocyanate) was prepared by mixing 46.6 parts by weight of Basonat® Hl 100 (polyisocyanate based on hexamethylene densocyanate from BASF AG), dissolved in 30 parts by weight of ethylethoxypropionate, with 23.4 parts by weight of 3.5 -D ⁇ methylpyrazol reacted for four hours at 50 0 C Thereafter, no free isocyanate groups were detectable for the preparation of the clear coat 1 25 parts by weight of the solution (A / B) and 16.6 parts by weight of TACT (T ⁇ s (alkoxycarbonylam ⁇ no) tr ⁇ az ⁇ n, see DE 199 40 855 A1, column 26, lines 27 to 53, in particular lines 49 to 53, compound C2) are mixed together, the resulting mixture was heated during one hour to 70 0 C, then that a clear solution was formed to this solution were 57.5 parts by weight of Solution of the blocked polyisocyanate (C1), 0.2 part by weight of By
  • test sheets used were steel sheets which had been coated with a customary and known, cathodically deposited and baked electro-dip coating.
  • Example 1 The clear coat 1 of Example 1 was applied to the Prufbleche Subsequently, the resulting clearcoat wet layers 1 baked together with the pre-dried Wasserfuller- layer and the pre-dried aqueous basecoat layer at 15O 0 C during 23 minutes The dry film thickness of the resulting clearcoats 1 was 40 microns
  • the resulting multicoat paint systems had an excellent overall appearance (appearance).
  • Your clear coats 1 had an excellent flow and were free from defects such as specks, craters, light / dark shades (clouds), pimples, pinpricks, orange peel and cracks. They were particularly clear and brilliant The clear coats 1 showed very good chemical resistance.
  • the gradient oven test showed the first damage from sulfuric acid only from 43 ° C, NaOH only from 61 0 C, pancreatin only from 37 ° C, tree resin only from 58 ° C and through distilled water only from 45 ° C. They were also scratch-resistant and in the car wash simulation test according to Amtec Kistler (cf. T Khmmasch and T Engbert, Technologietage, Cologne, DFO 1 report 32, pages 59 to 66, 1997) a residual shine after cleaning with white spirit from 58 units

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
  • Sealing Material Composition (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

L'invention concerne des mélanges liquides, thermodurcissables, comprenant : A) des polyols à faible poids moléculaire comprenant au moins trois groupes hydroxyle, la teneur en groupes hydroxyle correspondant à un nombre de OH théorique compris entre 800 et 1900 mg KOH/g ; B) des composés sélectionnés dans le groupe constitué d'alcanes C<SUB>9</SUB>-C<SUB>16</SUB> cycliques et acycliques qui peuvent être rendus fonctionnels par des groupes hydroxyle ou des groupes hydroxyle et au moins un groupe thiol ; et C) des composés à faible poids moléculaire ou oligomères comprenant des groupes (c1) fonctionnels, réactifs aux groupes hydroxyle et aux groupes thiol. L'invention concerne également un procédé de production des mélanges ainsi que leurs utilisations.
EP06819015A 2005-12-09 2006-12-08 Melanges liquides, thermodurcissables, procede de production et d'utilisation associes Withdrawn EP1960449A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005058891A DE102005058891A1 (de) 2005-12-09 2005-12-09 Flüssige, thermisch härtbare Gemische, Verfahren zu ihrer Herstellung und ihre Verwendung
PCT/EP2006/011851 WO2007065707A2 (fr) 2005-12-09 2006-12-08 Melanges liquides, thermodurcissables, procede de production et d'utilisation associes

Publications (1)

Publication Number Publication Date
EP1960449A2 true EP1960449A2 (fr) 2008-08-27

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP06819015A Withdrawn EP1960449A2 (fr) 2005-12-09 2006-12-08 Melanges liquides, thermodurcissables, procede de production et d'utilisation associes

Country Status (6)

Country Link
US (1) US20080293880A1 (fr)
EP (1) EP1960449A2 (fr)
JP (1) JP2009518478A (fr)
CN (1) CN101326211A (fr)
DE (1) DE102005058891A1 (fr)
WO (1) WO2007065707A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9580598B2 (en) * 2011-03-25 2017-02-28 Covestro Llc Polyurethane composites produced by a vacuum infusion process
CA2859278A1 (fr) * 2012-02-28 2013-09-06 Basf Coatings Gmbh Substance de revetement pigmentee et procede de realisation d'un laquage multicouche au moyen de cette substance de revetement pigmentee

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19855167A1 (de) * 1998-11-30 2000-05-31 Basf Coatings Ag Aus mindestens drei Komponenten bestehendes Beschichtungsmittel, Verfahren zu seiner Herstellung sowie seine Verwendung
DE19938758A1 (de) * 1999-08-16 2001-02-22 Basf Coatings Ag Oligomere und Polymere auf der Basis von Diethyloctandiolen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19940855A1 (de) * 1999-08-27 2001-03-01 Basf Coatings Ag Lösemittelhaltiger Beschichtungsstoff und seine Verwendung
DE19961926A1 (de) * 1999-12-22 2001-07-05 Basf Coatings Ag Thermisch mit aktinischer Strahlung härtbare Stoffgemische und ihre Verwendung
DE10001443A1 (de) * 2000-01-15 2001-07-26 Basf Coatings Ag Thixotropierungsmittel, Verfahren zu seiner Herstellung und seine Verwendung
DE10023229A1 (de) * 2000-05-12 2001-11-22 Basf Coatings Ag Mehrkomponentenbeschichtungsstoffe, -klebstoffe und -dichtungsmassen und ihre Verwendung
AU2001261642B2 (en) * 2000-05-18 2005-07-28 Akzo Nobel N.V. Aromatic polyurethane polyol
US6743466B2 (en) * 2001-08-03 2004-06-01 E. I. Du Pont De Nemours And Company Process for repairing coated substrate surfaces

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2007065707A2 *

Also Published As

Publication number Publication date
CN101326211A (zh) 2008-12-17
DE102005058891A1 (de) 2007-06-14
WO2007065707A3 (fr) 2007-11-22
WO2007065707A2 (fr) 2007-06-14
JP2009518478A (ja) 2009-05-07
US20080293880A1 (en) 2008-11-27

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