EP1989241A1 - Polyole auf der basis von modifizierten aminoplastharzen, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
Polyole auf der basis von modifizierten aminoplastharzen, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- EP1989241A1 EP1989241A1 EP07703383A EP07703383A EP1989241A1 EP 1989241 A1 EP1989241 A1 EP 1989241A1 EP 07703383 A EP07703383 A EP 07703383A EP 07703383 A EP07703383 A EP 07703383A EP 1989241 A1 EP1989241 A1 EP 1989241A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyols
- variable
- general formula
- coatings
- polyol
- 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- Withdrawn
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Classifications
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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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/44—Chemically modified polycondensates by esterifying
-
- 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
- C08G6/00—Condensation polymers of aldehydes or ketones only
- C08G6/02—Condensation polymers of aldehydes or ketones only of aldehydes with ketones
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- 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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C09D161/32—Modified amine-aldehyde condensates
Definitions
- the present invention relates to novel polyols based on modified aminoplast resins. Moreover, the present invention relates to a novel process for the modification of aminoplast resins. Last but not least, the present invention relates to the use of the novel polyols based on modified aminoplast resins as well as the polyols prepared with the aid of the novel process for the modification of aminoplast resins as curable materials or for their preparation.
- Aminoplast resins in particular acetalized or etherified melamine / formaldehyde resins, and their use as crosslinking agents in thermally curable materials, in particular coating materials, have long been known (cf., for example, Johan Bieleman, "Lackadditive”, “7.2.2 Melamine resin-crosslinking systems", Wiley-VCH, Weinheim, New York, 1998, pages 242-250).
- the relevant coating materials are known to provide coatings with high surface hardness.
- aminoplast resins tend to self-condense, which increases the brittleness of the coatings and reduces their elasticity.
- the aminoplast resins are also used as co-crosslinking agents in coating materials prepared from so-called multi-component systems, in particular two-component systems.
- the multicomponent systems comprise at least one binder component, which preferably contains hydroxyl-containing components, and at least one crosslinker component, which preferably contains polyisocyanates.
- the two components are stored separately from each other and mixed together just before use for the preparation of the actual coating material.
- the coatings produced from these coating materials are known to have advantageous property combinations, such as a good etch resistance and a good wet scratch resistance.
- acetalically bound alcohol can be split off from the aminoplast resins, whereby the original equivalent ratio of hydroxyl groups to isocyanate groups changes in an unpredictable manner.
- the liberated alcohol then inevitably forms network end groups by reaction with the polyisocyanates in the resulting thermoset material, which can adversely reduce the network density and hence the scratch resistance of the subject coatings.
- aminoplast resins with compounds containing a carbamate group, such as methyl carbamate, is known from US patent application US 2005/0182189 A1. This results in aminoplast resins containing groups of the formula> N-CH 2 -NH-C (O) -OCH 3 .
- aminoplast resins because of the lack of isocyanate-reactive functional groups, their high melting point and their high crosslinking temperatures, these amino resins are unsuitable as constituents of multicomponent systems.
- thermosetting materials are eminently useful as novel thermosetting materials or components for new thermosetting materials and which can be readily prepared from known, readily available starting materials.
- the new thermally curable materials should be stable on storage and transportable and are particularly suitable as new coating materials, adhesives, sealants and precursors for moldings and films, in particular coating materials, especially coating materials, which are prepared from multicomponent systems shortly before their use.
- the new coating materials are said to be outstandingly suitable as electrodeposition paints, primers, fillers, primers, basecoats, solid-color topcoats and clearcoats, especially clearcoats.
- the new thermosetting materials should also be ideal for the production of new thermoset materials, especially coatings, adhesive layers, gaskets, moldings and films, especially coatings.
- the new coatings are primarily intended for new electrodeposition coatings, primer coatings, surfacer coatings, antistonechip primers,
- the new coatings should have a high etch resistance, chemical resistance, weather resistance and moisture resistance, a very good flow, an excellent overall appearance (appearance), a very good wet scratch resistance and a particularly high dry scratch resistance.
- novel polyols (A) were found on the basis of modified aminoplast resins, preparable by the reaction of at least one aminoplast resin (B) with at least three acetalated or etherified N-methylol groups of the general formula I:
- variable R denotes a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms
- variable R 1 denotes an alkyl group having 1 to 6 carbon atoms
- index n is a number from 2 to 6 and the variable R 2 is a bivalent to six-bond organic radical; in an equivalent ratio IM:
- variable R 1 has the meaning given above; from the aminoplast resin (B).
- polyols (A) based on modified aminoplast resins are referred to below as "polyols (A) according to the invention.
- variable R denotes a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms
- variable R 1 denotes an alkyl group having 1 to 6 carbon atoms
- index n is a number from 2 to 6 and the variable R 2 is a bivalent to six-bond organic radical; in an equivalent ratio III:
- variable R 1 has the meaning given above; from the aminoplast resin (B).
- the novel process for preparing the polyols (A) according to the invention is referred to below as the "process according to the invention".
- polyols (A) according to the invention could be used excellently as new thermally curable materials or constituents for new thermally curable materials within the scope of the inventive use and prepared in a particularly simple manner from known, readily available starting materials using the process according to the invention could become.
- thermally curable materials according to the invention were storage-stable and transportable and were particularly suitable as new coating materials, adhesives, sealants and precursors for moldings and films, in particular coating materials, especially coating materials, which were prepared shortly before their use of multicomponent systems.
- the coating materials according to the invention were outstandingly suitable in particular as novel electrodeposition paints, primers, fillers, primers, basecoats, solid-color topcoats and clearcoats, especially clearcoats.
- thermoset materials especially Coatings, adhesive layers, gaskets, moldings and films, in particular coatings.
- the coatings according to the invention were, above all, novel electrodeposition coatings, primer coatings, surfacer coatings, antistonechip primers,
- the coatings according to the invention had a high etch resistance, chemical resistance, weathering resistance and moisture resistance, a very good flow, an excellent overall appearance (appearance), a very good wet scratch resistance and a particularly high dry scratch resistance.
- the coatings according to the invention in particular the clearcoats of the invention, were therefore outstandingly suitable for the coating of particularly high-grade economic goods, in particular automobile bodies and parts thereof.
- the preparation of the polyols (A) according to the invention in the context of the process according to the invention starts from at least one, in particular one, aminoplast resin (B) containing at least three, preferably at least four, preferably at least five and in particular six acetalated or etherified N-methylol groups of the general formula I:
- variable R denotes a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms, but especially a hydrogen atom
- variable R 1 denotes an alkyl group having 1 to 6, preferably 1 to 4, carbon atoms, in particular but methyl, butyl or isobutyl, called.
- the aminoplast resin (B) is selected from the group consisting of melamine, guanamine, urea and glycoluril resins as well as amides and compounds at least two carbamate groups selected.
- the aminoplast resin (B) is a melamine resin.
- aminoplast resins (B) are well-known compounds and are described, for example, in detail in US patent application US 2005/0182189 A1, page 1, paragraph [0014], to page 4, paragraph [0028].
- the aminoplast resin (B) is reacted with at least one polyol (C) and preferably at least two and in particular two polyols (C) of the general formula II:
- n is a number from 2 to 6, preferably an integer from 2 to 6, preferably 2 or 3 and especially 2 and the variable R 2 is a divalent to hexavalent, preferably divalent or trivalent and in particular divalent organic residue is; implemented.
- the organic radicals R 2 are preferably radicals which contain or consist of aliphatic, cycloaliphatic and / or aromatic groups.
- they contain 2 to 50, preferably 2 to 40, particularly preferably 2 to 30
- Carbon atoms may also contain functional groups which link the aliphatic, cycloaliphatic and / or aromatic groups with one another, as described, for example, in German Patent Application DE 199 47 523 A1, page 5, lines 38 to 47. In addition, they may be substituted. Examples of suitable
- Suitable polyols (C) are triols, tetrols, pentites and hexites, such as trimethylolmethane, trimethylolethane, trimethylolpropane, glycerol, erythritol, threitol, pentaerythritol, dipentaerythritol, homopentaerythritol, arabitol, adonite, xyNt, mannitol, sorbitol, dulcitol and inositol.
- suitable diols (C) are cyclic and acyclic which are functionalized with two hydroxyl groups.
- the C 9 -C 16 alkanes, from which the compounds (B) are derived from the group consisting of 2-methyloctane, 4-methyloctane, 2,3-dimethyl-heptane, 3,4-dimethyl-heptane , 2,6-dimethylheptane, 3,5-dimethylheptane, 2-methyl-4-ethylhexane, isopropylcyclohexane, 4-ethyloctane, 2,3,4,5-tetramethylhexane, 2,3 diethyl-hexane 1-methyl-2-n-propyl-cyclohexane, 2,4,5,6-tetramethyl-heptane, 3-methyl-6-ethyl-octane, 1 '-ethyl-butyl cyclohexane, 3 positionally Diethyloctane , 4-dimethyl-5-ethyl-nonane, 4,6-dimethyl-5
- the C 9 -C 16 -alkanes are preferably position-isomeric diethyloctanes.
- preferred compounds (B) are the positionally isomeric diethyloctanediols, more preferably those containing linear C 8 carbon chains.
- the C 8 carbon chain with respect to the two ethyl groups 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 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 selected from the group consisting of
- the two ethyl groups are in the 2,4-position.
- the two hydroxyl groups are preferably in the 1,5-position.
- 2,4-diethyloctane-1, 5-diol is used as the diol (C).
- the positionally isomeric diethyloctanediols (C) are compounds which are known per se and can be prepared by customary and known synthesis methods of organic chemistry, such as the base-catalyzed aldol condensation, or they are obtained as by-products of major chemical syntheses such as the preparation of 2-ethylhexanol.
- diols (C) are known from German patent application DE 199 48 004 A1, page 5, line 38, page 6, line 7.
- propylene glycol and hydroxypivalic acid neopentyl glycol esters are used.
- the aminoplast resin (B) and the polyol (C) are reacted with one another in a quantitative ratio such that an equivalent ratio III of
- Group I of (B): polyol (C) 0.5 to 1.2, preferably 0.6 to 1, and especially 1
- variable R 1 has the meaning given above; split off from the aminoplast resin (B).
- the monoalcohol (D) is methanol, n-butanol and isobutanol, especially methanol.
- the reaction is carried out at 80 to 150 c C.
- the monoalcohol (D) is preferably removed continuously from the reaction mixture.
- the reaction can be carried out in organic solution. Preferably, it is carried out in bulk.
- the aminoplast resin (B) and the polyol (C) are preferably carried out in the presence of a catalyst (E).
- An acid catalyst (E) is particularly preferably used.
- an acid catalyst (E) is used, as is commonly used for the condensation of melamine resins. Examples Suitable catalysts (E) are known from Johan Bieleman, "Paint Additives,””7.2.2 Melamine Resin Crosslinking Systems,” Wiley-VCH, Weinheim, New York, 1998, pages 242-250.
- the resulting polyols (A) according to the invention can serve a wide variety of uses. In the context of the inventive use, they preferably serve as thermally curable materials according to the invention or for the production of the thermally curable materials according to the invention.
- thermally curable materials according to the invention can also be curable physically, oxidatively and / or with actinic radiation.
- Actinic radiation is understood to mean electromagnetic radiation, such as near infrared (NIR), visible light, UV radiation, X-radiation and gamma radiation, in particular UV radiation, and corpuscular radiation, such as electron radiation, beta radiation, proton radiation, neutron radiation and alpha radiation, in particular electron radiation.
- NIR near infrared
- UV radiation visible light
- X-radiation and gamma radiation in particular UV radiation
- corpuscular radiation such as electron radiation, beta radiation, proton radiation, neutron radiation and alpha radiation, in particular electron radiation.
- novel materials are preferably used as new coating materials, adhesives, sealants and precursors for moldings and films curable thermally or thermally and with actinic radiation.
- the coating materials of the invention may be conventional coating materials based on organic solvents, aqueous coating materials, powdered coating materials or suspensions of powders (powder slurries). They can be one-component or multi-component systems, in particular
- Two-component systems be.
- they are two-component systems consisting of a binder component containing components having isocyanate-reactive functional groups, especially hydroxyl groups, and a crosslinker component containing polyisocyanates.
- novel coating materials are particularly preferably new electrodeposition paints, primers, fillers, primers, basecoats, solid-color topcoats and clearcoats, especially clearcoats.
- the preparation of the thermally curable materials according to the invention offers no special features, but they are obtained by mixing the polyols (A) according to the invention mixed with customary and known constituents of coating materials, after which the mixtures are homogenized.
- suitable mixing units for producing the thermally curable materials according to the invention are stirred tanks, inline dissolvers, rotor / stator dispersers, Ultraturrax, Microfluidizers, high-pressure homogenizers or jet-jet dispersants. If the thermally curable materials of the invention are to contain constituents which can be activated with actinic radiation, the exclusion of actinic radiation in the production and the subsequent storage of the thermally curable materials according to the invention is recommended.
- the content of the thermally curable materials according to the invention in the polyols (A) according to the invention can vary very widely and can thus be optimally adapted to the requirements of the individual case.
- the content of (A) is preferably from 5 to 95% by weight, preferably from 5 to 90% by weight, particularly preferably from 10 to 80% by weight and in particular from 10 to 70% by weight, in each case based on the solids of the coating material according to the invention, where "solid” is understood to be the sum of all constituents which build up the thermosetting material produced from the thermally curable material according to the invention
- the usual and known constituents of the coating materials are selected from the group consisting of oxidatively, physically, thermally and / or with actinic radiation-curable binders, crosslinking agents, neutralizing agents; organic solvents, thermal reactant thermally curable with actinic radiation and thermally and with actinic radiation; transparent and opaque, coloring, effecting and coloring and effect pigments; transparent and opaque fillers; nanoparticles; molecularly soluble dyes; Light stabilizers; antioxidants; Neutralizing agents; Wetting agents; emulsifiers; slip additives; polymerization inhibitors; Catalysts for thermal crosslinking; thermolabile radical initiators; Photoinitiators and co-initiators; Adhesion promoters; Leveling agents; film-forming aids; rheological; Flame retardants; Corrosion inhibitors; To grow; driers; Biocides and matting agents; selected.
- thermally curable materials according to the invention are clearcoats or precursors for clear films and moldings, they contain no opaque constituents.
- suitable constituents of coating materials are known from German patent application DE 199 14 899 A1, page 14, line 36, to page 16, line 63, page 17, line 7, to page 18, line 13, page 18, lines 16 to 21, Page 19, lines 10 to 22 and 30 to 61, known.
- thermoset materials of the invention are used in the context of the inventive use of the preparation of the thermoset materials of the invention.
- thermoset materials according to the invention are preferably novel coatings, adhesive layers, seals, moldings and films, in particular new coatings.
- the coatings according to the invention are preferably new electrodeposition coatings
- Primer coatings surfacer coatings or antistonechip primers
- Basecoats solid-color topcoats and clearcoats, especially clearcoats.
- These coatings according to the invention may be single-layered or multi-layered. Most preferably, they are multi-layered and may comprise at least two finishes, in particular at least one electrodeposition coating, at least one surfacer or antistonechip primer and at least one basecoat and at least one clearcoat or at least one solid-color topcoat.
- the multicoat paint systems according to the invention comprise at least one basecoat and at least one clearcoat.
- the clearcoats of the invention are the outermost layer of the multicoat system of the invention, which substantially determines the overall visual appearance (appearance) and protects the color and / or effect basecoats against mechanical and chemical damage and radiation damage.
- the clearcoats of the invention prove to be as particularly insensitive to mechanical stress such as tensile, elongation, impact, scratching or abrasion, as particularly resistant to moisture (eg in the form of water vapor), solvents and diluted chemicals and as particularly resistant to environmental influences such as
- the materials according to the invention are applied to temporary or permanent substrates.
- conventional and known temporary substrates are preferably used, such as metal and plastic tapes or hollow bodies of metal, glass, plastic, wood or ceramic, which can be easily removed without damaging the films and moldings according to the invention ,
- mixtures according to the invention are used for the production of coatings, adhesives and seals, permanent substrates are used.
- the substrates are um
- land, sea or air powered means of muscle, hot air or wind such as bicycles, trolleys, rowing boats, sailboats, hot air balloons, gas balloons or gliders, and parts thereof, powered by land, sea or air, such as motorcycles, commercial vehicles or motor vehicles, in particular cars, over- or
- stationary buoys such as buoys or parts of docks, indoor and outdoor structures, doors, windows and furniture, and - glass hollow bodies, industrial small parts such as screws, nuts, end caps or rims, Containers, such as coils, containers or packaging, electrotechnical components, such as electronic winding goods, such as coils, optical components, mechanical components and - white goods, such as household appliances, boilers and radiators.
- the films and moldings according to the invention can likewise serve as substrates.
- the substrates are automobile bodies and parts thereof.
- the thermally curable materials according to the invention or the coatings produced therefrom according to the invention are preferably used for this purpose
- the first coatings according to the invention in particular those which contain a clearcoat according to the invention, have excellent recoatability.
- the refinishes according to the invention are excellently adhering to the novel and noninventive primary finishes.
- the application of the thermally curable materials according to the invention has no special features, but can by all customary and known, suitable for the respective mixture application methods, such as. Electrocoating, spraying, spraying, knife coating, brushing, pouring, dipping, trickling or rolling take place. Preferably, spray application methods are used.
- thermally curable materials according to the invention are additionally curable with actinic radiation.
- the flash-off time or rest time may have a duration of 30 seconds to 2 hours, preferably 1 minute to 1 hour and especially 1 to 45 minutes.
- the rest period is used for example for the course and the
- the ventilation can be accelerated by an increased temperature and / or by a reduced humidity.
- the thermal curing of the applied materials according to the invention can be accelerated, for example, by the action of a gaseous, liquid and / or solid, hot medium, such as hot air, heated oil or heated rollers, or microwave radiation, infrared light and / or near infrared light (NIR).
- a gaseous, liquid and / or solid, hot medium such as hot air, heated oil or heated rollers, or microwave radiation, infrared light and / or near infrared light (NIR).
- the heating takes place in a circulating air oven or by irradiation with IR and / or NIR lamps.
- the curing with actinic radiation can with the aid of conventional and known devices and methods, as described for example in German Patent Application DE 198 18 735 A 1, column 10, lines 31 to 61, the German patent application DE 102 02 565 A1, page 9, Paragraph [0092], to page 10, paragraph [0106], German patent application DE 103 16 890 A1, page 17, paragraphs [0128] to [0130], in the international patent application WO 94/11123, page 2, lines 35, to page 3, line 6, page 3, lines 10 to 15, and page 8, lines 1 to 14, or US patent US 6,743,466 B2, column 6, line 53, to column 7, line 14 ,
- the curing of the thermally curable materials according to the invention can also be carried out with substantial or complete exclusion of oxygen.
- the oxygen is considered largely excluded if its concentration at the surface of the applied mixtures according to the invention ⁇ 21 vol .-%, preferably ⁇ 18 vol .-%, preferably ⁇ 16 vol .-%, particularly preferably 14 vol. -%, most preferably 10 vol .-% and in particular ⁇ 6 vol .-%.
- the oxygen is considered completely excluded if its concentration at the surface is below the detection limit of the usual and known detection methods.
- concentration of oxygen is preferably> 0.001% by volume, more 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 adjusted by the measures described in German Patent DE 101 30 972 C1, page 6, paragraphs [0047] to [0052], or by the application of films.
- thermoset materials according to the invention preferably the films, moldings, coatings, adhesive layers and gaskets according to the invention, particularly preferably the inventive coatings, very particularly preferably the electrodeposition coatings of the invention, primer coatings, surfacers or antistonechip primers, basecoats, solid-color topcoats and clearcoats, in particular the clearcoats of the invention , are eminently suitable for coating, gluing, sealing, wrapping and packaging the primed or unprimed substrates described above as well as for attachment to or incorporation into the primed or unprimed substrates described above.
- the resulting substrates according to the invention which are coated with coatings according to the invention, bonded to adhesive layers according to the invention, sealed with gaskets according to the invention and / or enveloped, packed and / or bonded with films and / or molded parts according to the invention have outstanding performance properties combined with a particularly long service life.
- the polyol (A1) was outstandingly suitable for the production of coating materials, adhesives, sealants and precursors for moldings and films. In particular, it was eminently suitable for the production of multicomponent systems comprising polyisocyanate-containing crosslinker components.
- Example 2 Analogously to the experimental procedure given in Example 1, the polyols (A2) to (A5) were prepared from the starting materials indicated in Table 1. The same HMMM as in Example 1 was used. The listed parts are parts by weight. Essential properties of the resulting polyols (A2) to (A5) can also be found in Table 1.
- the polyols (A2) to (A5) were also outstandingly suitable for the production of coating materials, adhesives, sealants and precursors for moldings and films. In particular, they were eminently suitable for the production of multicomponent systems containing polyisocyanates
- a hydroxyl-containing methacrylate copolymer was first prepared as a binder according to the following experimental procedure.
- an initiator solution of 153.4 parts by weight of tert-butyl perethylhexanoate and from the other feed vessel was heated for 4.5 hours 92.4 parts by weight of pentyl acetate added uniformly to the template.
- the reaction mixture was postpolymerized for 2 hours at 137 0 C.
- the resulting binder solution was diluted with pentyl acetate to a solids content of 65 wt .-% (determined in a convection oven for one hour at 130 0 C).
- the hydroxyl number was 185 mg KOH / g of solid resin, corresponding to a hydroxy equivalent weight of 303.
- Table 2 gives an overview of the composition of the clearcoats 1 to 4 of Examples 6 to 9 and the clearcoat V1 of Comparative Experiment V1.
- Binder component
- Binder solution 1 0.6 0.6 0.6 0.5
- the binder components of Examples 6 to 9 of Table 2 were transportable and could be stored for months without any settling or segregation of ingredients or viscosity increase.
- the clearcoats 1 to 4 and V1 prepared from the two-component systems of Examples 6 to 9 and Comparative Experiment V1 had a pot life or processing time within which they could be applied without problems of several hours. For the application, they were adjusted to a spray viscosity of 25 to 30 seconds in the DIN4 cup by addition of butyl acetate.
- the clearcoat 1 of Example 6 was used.
- the clearcoat material 2 of Example 7 was used.
- Example 12 For the preparation of the multi-layer coating 3 of Example 12, the clearcoat 3 of Example 8 was used.
- Black multicoat paint systems were produced because they were particularly good at evaluating flow, appearance and scratch resistance. They were prepared according to the following general experimental procedure.
- the clearcoat materials were applied uniformly in each case in two spray passes with a 4-minute flash-off time, resulting in a dry film thickness of 50 ⁇ m.
- the resulting clearcoat films were flashed off for 10 minutes at room temperature and dried for 45 minutes at 6O 0 C in a forced air oven.
- the gloss (20 °) was measured according to DIN 67530.
- V2 / V1 good gloss 76/89 84 35
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006006130A DE102006006130A1 (de) | 2006-02-10 | 2006-02-10 | Polyole auf der Basis von modifizierten Aminoplastharzen, Verfahren zu ihrer Herstellung und Ihre Verwendung |
PCT/EP2007/001141 WO2007090679A1 (de) | 2006-02-10 | 2007-02-09 | Polyole auf der basis von modifizierten aminoplastharzen, verfahren zu ihrer herstellung und ihre verwendung |
Publications (1)
Publication Number | Publication Date |
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EP1989241A1 true EP1989241A1 (de) | 2008-11-12 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP07703383A Withdrawn EP1989241A1 (de) | 2006-02-10 | 2007-02-09 | Polyole auf der basis von modifizierten aminoplastharzen, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (6)
Country | Link |
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US (1) | US8153752B2 (de) |
EP (1) | EP1989241A1 (de) |
JP (1) | JP5361397B2 (de) |
CN (1) | CN101384635B (de) |
DE (1) | DE102006006130A1 (de) |
WO (1) | WO2007090679A1 (de) |
Citations (3)
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EP0940459A2 (de) * | 1998-03-06 | 1999-09-08 | BASF Coatings Aktiengesellschaft | Beschichtungsmittel und Klebstoffe, ihre Verwendung und Verfahren zu ihrer Herstellung |
WO2001012696A1 (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 |
WO2003061965A1 (de) * | 2002-01-25 | 2003-07-31 | Basf Coatings Ag | Verwendung von polyhydroxyfunktionalisierten alkanen als haftvermittler in verbunden aus beschichtung, klebschicht und verbundglasscheibe sowie verbunde dieser art, verfahren zu ihrer herstellung und ihre verwendung |
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DE1049094B (de) * | 1956-09-01 | 1959-01-22 | Bayer Ag | Verfahren zur Herstellung von linearen oder verzweigten N-Methylenoxygruppen enthaltenden Polyaethern |
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JPS6035060A (ja) * | 1983-08-05 | 1985-02-22 | Dainippon Ink & Chem Inc | 塗料用樹脂組成物 |
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JPS61246273A (ja) * | 1985-04-25 | 1986-11-01 | Dainippon Ink & Chem Inc | 顔料ベ−スト |
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-
2006
- 2006-02-10 DE DE102006006130A patent/DE102006006130A1/de not_active Withdrawn
-
2007
- 2007-02-09 US US12/160,348 patent/US8153752B2/en not_active Expired - Fee Related
- 2007-02-09 CN CN2007800051001A patent/CN101384635B/zh not_active Expired - Fee Related
- 2007-02-09 EP EP07703383A patent/EP1989241A1/de not_active Withdrawn
- 2007-02-09 WO PCT/EP2007/001141 patent/WO2007090679A1/de active Application Filing
- 2007-02-09 JP JP2008553689A patent/JP5361397B2/ja not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0940459A2 (de) * | 1998-03-06 | 1999-09-08 | BASF Coatings Aktiengesellschaft | Beschichtungsmittel und Klebstoffe, ihre Verwendung und Verfahren zu ihrer Herstellung |
WO2001012696A1 (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 |
WO2003061965A1 (de) * | 2002-01-25 | 2003-07-31 | Basf Coatings Ag | Verwendung von polyhydroxyfunktionalisierten alkanen als haftvermittler in verbunden aus beschichtung, klebschicht und verbundglasscheibe sowie verbunde dieser art, verfahren zu ihrer herstellung und ihre verwendung |
Non-Patent Citations (1)
Title |
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See also references of WO2007090679A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2007090679A1 (de) | 2007-08-16 |
JP2009526106A (ja) | 2009-07-16 |
JP5361397B2 (ja) | 2013-12-04 |
US20100273975A1 (en) | 2010-10-28 |
DE102006006130A1 (de) | 2007-08-16 |
US8153752B2 (en) | 2012-04-10 |
CN101384635A (zh) | 2009-03-11 |
CN101384635B (zh) | 2011-08-17 |
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