WO2007025722A2 - Utilisation d'alcools gras alcoxyles dans des suspensions de vernis clair a viscosite intrinseque, suspension de vernis clair a viscosite intrinseque, et procede de production et utilisation de cette suspension de vernis clair a viscosite intrinseque - Google Patents

Utilisation d'alcools gras alcoxyles dans des suspensions de vernis clair a viscosite intrinseque, suspension de vernis clair a viscosite intrinseque, et procede de production et utilisation de cette suspension de vernis clair a viscosite intrinseque Download PDF

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Publication number
WO2007025722A2
WO2007025722A2 PCT/EP2006/008457 EP2006008457W WO2007025722A2 WO 2007025722 A2 WO2007025722 A2 WO 2007025722A2 EP 2006008457 W EP2006008457 W EP 2006008457W WO 2007025722 A2 WO2007025722 A2 WO 2007025722A2
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WIPO (PCT)
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groups
clearcoat slurry
slurry
slurry according
slurries
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PCT/EP2006/008457
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German (de)
English (en)
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WO2007025722A3 (fr
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Michael Tecklenborg
Bianca Giesen
Marco Deyda
Hubert Baumgart
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Basf Coatings Ag
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Publication of WO2007025722A2 publication Critical patent/WO2007025722A2/fr
Publication of WO2007025722A3 publication Critical patent/WO2007025722A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/10—Homopolymers or copolymers of methacrylic acid esters
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • C09D5/027—Dispersing agents

Definitions

  • the present invention relates to the novel use of alkoxylated fatty alcohols in pseudoplastic clearcoat slurries.
  • the present invention relates to a novel pseudoplastic clearcoat slurry.
  • the present invention relates to a novel process for the preparation of a pseudoplastic clearcoat slurry.
  • the present invention relates to the use of the new pseudoplastic clearcoat slurry for automotive finishing, automotive refinishing, painting of buildings indoors and outdoors, the painting of doors, windows and furniture and industrial coating, including coil coating, container coating , the small parts painting, the impregnation and / or coating of electrical components and the painting of white goods.
  • WO 03/010247 discloses a pseudoplastic clearcoat slurry comprising solid and / or highly viscous particles dimensionally stable under storage and application conditions and at least one wetting agent selected from the group consisting of alkoxylated fatty alcohols having 16 to 18 carbon atoms in the Alkyl radical and on average at least 20 oxaalkandiyl groups in the molecule.
  • the known pseudoplastic clearcoat slurry has a good filterability and a good gear pump handling. It provides clearcoats that have very good optical properties (appearance) and high chemical resistance.
  • the particle size distribution of the known pseudoplastic clearcoat slurry is comparatively broad after its preparation, changes over time and only stabilizes after a storage time of several weeks. That is, the known pseudoplastic clearcoat slurry shows an aging effect. However, this aging effect must be taken into account by the manufacturer and user in order to avoid disadvantages, which increases the logistical effort in the production, handling and application. In addition, the known pseudoplastic clearcoat slurry must be further improved in their stability to sedimentation, their filterability and their gear pump passability.
  • the clearcoats produced from the known pseudoplastic clearcoat slurry must be steadily improved in their chemical stability, weather resistance and the occurrence of paint defects, such as craters or micro-disturbances (starry sky).
  • the object of the present invention is to provide a novel pseudoplastic clearcoat slurry whose performance profile is further improved in comparison with that of the known pseudoplastic clearcoat slurry.
  • the particle size distribution of the novel pseudoplastic clearcoat slurry should be comparatively narrow after its preparation, do not change over time and should be stable immediately after its preparation and not only after a storage time of several weeks. That is, the new pseudoplastic clearcoat slurry no longer show any aging effect, which can be reduced in the manufacturer and user logistical effort in the production, handling and application
  • the known pseudoplastic clearcoat slurry should be further improved in their stability to sedimentation, their filterability and their gear pump passability.
  • the clearcoats produced from the known pseudoplastic clearcoat slurry should be further improved in their chemical stability, weather resistance and the occurrence of paint defects, such as craters or micro-disturbances (starry sky).
  • the slurry according to the invention had a narrow particle size distribution which did not change over time and already immediately after the preparation of the slurry according to the invention and not only after a storage time of several
  • the slurry of the invention exhibited significantly improved stability to sedimentation, significantly improved filterability, and significantly improved gear pump handling.
  • the clearcoats produced from the slurry of the invention were significantly improved in their chemical stability and weather resistance. If anything, paint disturbances, such as craters or micro-disturbances (starry skies), occurred only very occasionally.
  • wetting agents selected from the group consisting of alkoxylated fatty alcohols having 8 to 15 carbon atoms in the alkyl radical and on average 3 to 19 oxaalkanediyl groups in the molecule are used in pseudoplastic clearcoat slurries.
  • the alkyl radical of the alkoxylated fatty alcohol preferably contains 9 to 15, preferably 10 to 14, particularly preferably 5 to 15 and in particular 13 carbon atoms.
  • the alkyl radical can be linear or branched. Preferably, it is branched. In particular, the alkyl radical is isotridecyl (1-C13H 2 7).
  • the alkoxylated fatty alcohol contains on statistical average preferably 5 to 15, preferably 7 to 14, particularly preferably 8 to 12 and in particular 10 oxaalkandiyl groups in the molecule.
  • the oxaalkanediyl groups are selected from the group consisting of 1-oxapropane-1, 3-diyl, 1-oxabutane-1, 4-diyl, 1-oxabutane-1,3-diyl, 1-oxapentane-1, 5 diyl or 1-oxapentane-1,3-diyl, preferably 1-oxapropane-1,3-diyl and 1-oxabutane-1,3-diyl.
  • the oxaalkanediyl group is 1-oxapropane-1,3-diyl (ethylene oxide group).
  • the alkoxylated fatty alcohols to be used according to the invention are commercially available wetting agents and are obtained, for example, from BASF Aktiengesellschaft under the Lutensol® TO brand sold.
  • Lutensol® TO 10 iC 13 H 27 O- (-CH 2 CH 2 O-) 10 -H]
  • Lutensol® 109 mixture of 85% Lutensol® TO 10 and 15% water
  • the amount of wetting agent to be used according to the invention in the pseudoplastic clearcoat slurries can vary widely. It is a very particular advantage of the use according to the invention that comparatively small amounts of wetting agents can be used in order to achieve the advantages of the invention.
  • the wetting agents to be used according to the invention are used in an amount of 0.01 to 2.5, preferably 0.05 to 2.4, particularly preferably 0.1 to 2.2, very particularly preferably 0.15 to 2 and in particular 0, 2 to 1, 8 wt .-%, each based on a given clearcoat slurry used.
  • wetting agents in international patent application WO 03/010247, page 9, line 17 to page 10, line 18, are selected from the group consisting of alkoxylated fatty alcohols having 16 to 18 carbon atoms in the alkyl radical and, on a statistical average, at least 20 oxaalkanediyl groups in the molecule.
  • the ratio (i): (ii) is 9: 1 to 1: 9, preferably 2.5: 7.5 to 7.5: 2.5, more preferably 4.5: 6.5 to 6.5 : 4,5 and especially 1.
  • the use according to the invention is directed to pseudoplastic clearcoat slurries.
  • the viscosity behavior referred to as "structurally viscous” describes a state which, on the one hand, meets the requirements of spray application and, on the other hand, also the requirements with regard to storage and settling stability: In the agitated state, for example when pumping the pseudoplastic clearcoat slurry in the ring line of the paint shop and in the Spraying, takes the pseudoplastic clearcoat slurry one low-viscosity state, which ensures good processability.
  • the pseudoplastic clearcoat slurries which are suitable for the use according to the invention can be of very different composition.
  • the slurries of the invention described below are used.
  • the slurries according to the invention contain solid and / or highly viscous particles which are dimensionally stable under conditions of storage and use and have the following monomodal particle size distribution measured by the laser diffraction method:
  • D (v, 0.1) 0.8 to 1.2 ⁇ m, preferably 0.9 to 1, 1 ⁇ m and in particular 0.95 to 1.1 ⁇ m;
  • D (v, 0.5) 1, 5 to 2.5 microns, preferably 1, 6 to 2.4 microns and especially 1, 7 to
  • the laser diffraction method is a customary and known method for measuring particle sizes and their distribution and can be carried out, for example, with the aid of the Mastersizer® from Malvern Instruments.
  • the particle size distribution of the slurry of the invention to be used according to the invention can be adjusted in any desired manner.
  • the particle size distribution results due to the use according to the invention.
  • the slurry according to the invention preferably contains the wetting agents to be used according to the invention described above, more preferably in the amounts indicated above.
  • the slurries according to the invention can have a wide variety of material compositions. For example
  • Patent application EP 0 899 282 A 1 prepared by secondary dispersion methods, thermally or thermally curable and with actinic radiation clearcoat slurries
  • the clearcoat slurries prepared by the secondary dispersion process which contain the special methacrylate copolymers described below as binders in the dimensionally stable particles.
  • the slurry according to the invention contains dimensionally stable particles.
  • "dimensionally stable" means that under the customary and known conditions of storage and application of clearcoat slurries, the particles only slightly agglomerate, if at all, and / or disintegrate into smaller particles, but also under the influence of shear forces
  • the particles may be highly viscous and / or solid, preferably the dimensionally stable particles are solid.
  • the slurry according to the invention preferably has a content of potentially ionic groups of from 0.05 to 1, preferably from 0.05 to 0.9, preferably from 0.05 to 0.8, particularly preferably from 0.05 to 0.7 and in particular from 0.05 to 0.6 meq / g solids.
  • the amount of neutralizing agent is chosen so that the degree of neutralization is 100%, preferably less than 80%, more preferably less than 60% and in particular less than 50%.
  • the chemical nature of the binder is generally not limitative in this respect as long as it contains ion-forming groups which can be converted into salt groups by neutralization and thereby can take on ionic stabilization of the particles in water.
  • Suitable anionic groups are acid groups such as carboxylic acid, sulfonic acid or phosphonic acid groups, in particular carboxylic acid groups, into consideration. Accordingly, bases such as alkali metal hydroxides, ammonia or amines are used as the neutralizing agent. Alkali metal hydroxides can be used only to a limited extent, since the alkali metal ions are not volatile during firing and, as a result of their incompatibility with organic substances, can cloud the film and lead to loss of gloss. Therefore, ammonia or amines are preferred. In the case of amines, tertiary amines are preferred. Examples include N, N-dimethylethanolamine or aminomethylpropanolamine (AMP) called.
  • bases such as alkali metal hydroxides, ammonia or amines are used as the neutralizing agent. Alkali metal hydroxides can be used only to a limited extent, since the alkali metal ions are not volatile during firing and, as a result of their incompatibility with organic substances,
  • Cation-forming groups are primary, secondary or tertiary amines. Accordingly, low molecular weight organic acids such as formic acid, acetic acid, dimethylolpropionic acid or lactic acid are used as the neutralizing agent.
  • polymers or oligomers having acid groups are preferred as ion-forming groups, since these so-called anionic binders in the Usually have a better resistance to yellowing than the class of cationic binder.
  • cationic binders with groups which can be converted into cations such as amino groups
  • cationic binders with groups which can be converted into cations can also be used in principle, provided that the field of application cope with their typical secondary properties, such as their tendency to yellow.
  • Suitable binders are random, alternating and / or block-structured linear and / or branched and / or comb-like (co) polymers of ethylenically unsaturated monomers, polyaddition resins and / or polycondensation resins. These terms are supplemented by Römpp Lexikon Lacke and Druckmaschine, Georg Thieme Verlag, Stuttgart, New York, 1998, page 457, "polyaddition” and “polyaddition resins (polyadducts)", and pages 463 and 464, “polycondensates”, “polycondensation” and “Polykondensationsharze", and pages 73 and 74, "binder", referenced.
  • suitable (co) polymers are (meth) acrylate (co) polymers or partially saponified polyvinyl esters, in particular (meth) acrylate copolymers.
  • suitable polyaddition resins and / or polycondensation resins are polyesters, alkyds, polyurethanes, polylactones, polycarbonates, polyethers, epoxy resins, epoxy resin-amine adducts, polyureas, polyamides, polyimides, polyester-polyurethanes, polyether-polyurethanes or polyester-polyether-polyurethanes.
  • the (meth) acrylate copolymers, the polyesters, the alkyd resins, the polyurethanes and / or the acrylated polyurethanes are advantageous and are therefore used with preference.
  • reactors for the copolymerization are the customary and known stirred tank, stirred tank cascades, tubular reactors, loop reactors or Taylor reactors, as described, for example, in the patent applications DE 1 071 241 B 1, EP 0 498 583 A1 or DE 198 28 742 A1 or in the article by K. Kataoka in Chemical Engineering Science, Vol. 50, No. 9, 1995, pages 1409-1416.
  • the (meth) acrylate comonomers containing potentially ionic groups are preferably acrylic acid, beta-carboxyethyl acrylate and / or methacrylic acid, in particular methacrylic acid.
  • the (meth) acrylate comonomers containing potentially ionic groups are polymerized into the methacrylate copolymers in an amount such that the above-described content of the particles of potentially ionic groups can be easily adjusted.
  • the methacrylate copolymers have a glass transition temperature Tg of at most 50 0 C on;
  • the glass transition temperature Tg should preferably 1 O preferably 10 and especially not less than 2O 0 C.
  • the glass transition temperature Tg of the methacrylate copolymers is preferably set via at least one methacrylate comonomer free of reactive functional groups and of potentially ionic groups.
  • the glass transition temperature Tg is preferably set via at least two, in particular two, methacrylate comonomers free of reactive functional groups and of potentially ionic groups.
  • the glass transition temperatures Tg of the respective homopolymers of the soft free from reactive functional groups and from potentially ionic groups methacrylate comonomers at most 4O 0 C from one another.
  • Suitable methacrylate comonomers free of reactive functional groups and of potentially ionic groups are methyl, ethyl, n-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl, isoamyl, cyclopentyl , n-hexyl and cyclohexyl methacrylate.
  • i-butyl methacrylate glass transition temperature Tg of the homopolymer: 53 ° C.
  • n-butyl methacrylate glass transition temperature Tg of the homopolymer: 20 ° C.
  • the amount of methacrylate comonomers copolymerized in the methacrylate copolymers to be used according to the invention and free of reactive functional groups and of potentially ionic groups may vary widely. It is essential that the amount is chosen so that the resulting methacrylate copolymers have the glass transition temperature Tg described above. Preferably, the amount is at least 50, preferably at least 55, more preferably at least 60, most preferably at least 65 and in particular at least 70 wt .-%, each based on a given Methacrylatcopolymerisat.
  • the weight ratio of the particularly preferred methacrylate comonomer n-butyl methacrylate and i-butyl methacrylate vary widely.
  • the weight ratio n: i is preferably 10: 1 to 1: 8, preferably 8: 1 to 1: 4, more preferably 6: 1 to 1: 2, very particularly preferably 5: 1 to 1: 1, 5 and in particular 4: 1 to 1: 1.
  • the methacrylate copolymers contain no or only a small number of reactive functional groups which are insignificant for crosslinking.
  • the methacrylate copolymers contain the complementary reactive functional groups described below for thermal crosslinking and / or reactive functional groups which can crosslink "with themselves", ie groups of their own type.
  • the methacrylate copolymers may contain reactive functional groups having at least one bond activatable with actinic radiation. These reactive functional groups are compulsorily included in the methacrylate copolymers of the actinic radiation-curable slurries of the invention if the slurries contain no further radiation-curable constituents.
  • the methacrylate copolymers contain reactive functional groups for thermal crosslinking and / or contain reactive functional groups having at least one bond activatable with actinic radiation.
  • the reactive functional groups having at least one bond activatable with actinic radiation are compulsorily contained in the methacrylate copolymers of the dual-cure slurries according to the invention if the dual-cure slurries contain no further radiation-curable constituents.
  • variable R is an acyclic or cyclic aliphatic, an aromatic and / or an aromatic-aliphatic (araliphatic) radical; the variables R and R stand for identical or different aliphatic radicals or are linked together to form an aliphatic or heteroaliphatic ring.
  • Overview Examples of complementary reactive functional groups
  • the selection of the respective complementary reactive functional groups is based on the fact that in the preparation of the binders and in the production, storage, application and melting of the slurries according to the invention, they do not give rise to any undesired reactions, in particular no formation of polyelectrolyte complexes or premature crosslinking , enter and / or the curing with actinic radiation should not disturb or inhibit, and secondly thereafter, in which temperature range the crosslinking should take place.
  • crosslinking temperatures of 60 to 18O 0 C are applied in the slurries invention.
  • binders with thio, hydroxyl, N-methylolamino-N-alkoxymethylamino, imino, carbamate and / or allophanate groups preferably hydroxyl groups
  • the binders contain in particular methylol, methylol ether and / or N-alkoxymethylamino groups.
  • Complementary reactive functional groups which are suitable for use in the thermally externally crosslinking slurries according to the invention and the dual-cure copolymers according to the invention. Slurries are particularly well suited, hydroxyl groups on the one hand and blocked isocyanate groups on the other.
  • Crosslinking density which one wants to achieve, and / or according to the functionality of the particular crosslinking agent used.
  • crosslinking agent for example, in the case of hydroxyl-containing crosslinking agent
  • Binders the OH number preferably at 20 to 300, preferably 40 to 250, more preferably 60 to 200, most preferably 80 to 190 and especially 90 to 180 mg KOH / g.
  • the complementary reactive functional groups described above can be incorporated into the binders by the usual and known methods of polymer chemistry. This can be done, for example, by the incorporation of methacrylate comonomers bearing the corresponding reactive functional groups and / or by means of polymer-analogous reactions.
  • Suitable methacrylate comonomers having reactive functional groups are methacrylate comonomers bearing at least one hydroxyl, amino, alkoxymethylamino, carbamate, allophanate or imino group per molecule, such as
  • Hydroxyalkyl esters of methacrylic acid derived from an alkylene glycol esterified with the acid or obtainable by reacting the methacrylic acid with an alkylene oxide such as ethylene oxide or propylene oxide, in particular hydroxyalkyl esters of methacrylic acid in which the hydroxyalkyl group is up to 20
  • Containing carbon atoms such as 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 3-hydroxybutyl or 4-hydroxybutyl methacrylate; or hydroxycycloalkyl esters such as 1,4-bis (hydroxymethyl) cyclohexane, octahydro-4,7-methano-1H-indenedimethanol or methylpropanediol monomethacrylate; or reaction products of cyclic esters, e.g. epsilon-caprolactone and these hydroxyalkyl methacrylates;
  • Aminoethyl methacrylate or N-methylaminoethyl methacrylate which may also serve to introduce potentially ionic groups
  • Methacrylic acid amides such as methacrylamide, N-methyl, N-methylol, N, N
  • Methacryloyloxyethyl, propyl or butyl carbamate or allophanate are described in US Pat. Nos. 3,447,328, 3,674,838, 4,126,747, 4,279,833, or 4,340,497;
  • the reactive functional groups for the thermal crosslinking of other olefinically unsaturated monomers such as the corresponding acrylates, allylamine, allyl alcohol or polyols, such as
  • Trimethylolpropanmono- or diallyl ether or pentaerythritol mono-, di- or - triallyl ether introduced.
  • the binders of the dual-cure slurries may contain on statistical average at least one, preferably at least two, group (s) having at least one bond (s) activatable with actinic radiation per molecule.
  • a bond which can be activated by actinic radiation is understood to mean a bond which becomes reactive upon irradiation with actinic radiation and undergoes polymerization reactions and / or crosslinking reactions with other activated bonds of its type which proceed by free-radical and / or ionic mechanisms.
  • suitable bonds are carbon-hydrogen single bonds or carbon-carbon, carbon-oxygen, carbon-nitrogen, carbon-phosphorus or carbon-silicon single bonds or double bonds.
  • the carbon-carbon double bonds are particularly advantageous and therefore very particularly preferably used according to the invention. For the sake of brevity, they will be referred to as "double bonds" in the following.
  • the preferred group according to the invention contains one double bond or two, three or four double bonds. If more than one double bond is used, the double bonds may be conjugated. According to the invention, however, it is advantageous if the double bonds are present in isolation, in particular each terminally, in the group in question here. According to the invention, it is particularly advantageous to use two, in particular one, double bond.
  • the dual-cure binder contains on a statistical average at least one of the actinic radiation activatable groups described above.
  • the functionality of the binder in this regard is an integer, i.e. equal to, for example, two, three, four, five or more, or non-integer, i.e., for example equal to 2.1 to 10.5 or more. Which functionality you choose depends on the requirements of the respective dual-cure slurries.
  • the groups are structurally different or of the same structure.
  • Suitable groups are (meth) acrylate, ethacrylate, crotonate, cinnamate, vinyl ether, vinyl ester, dicyclopentadienyl, norbomenyl, isoprenyl, isopropenyl, allyl or butenyl groups; Dicyclopentadienyl, norbomenyl, isoprenyl, isopropenyl, allyl or butenyl ether groups or dicyclopentadienyl, norbornyl, isoprenyl, isopropenyl, allyl or butenyl ester groups, but especially acrylate groups.
  • the groups are bonded via urethane, urea, allophanate, ester, ether and / or Amid ferry ⁇ , but in particular via ester groups, to the respective basic structures of the binder.
  • This is usually done by conventional and known continuous polymer-analogous reactions such as the reaction of pendant glycidyl groups with olefinically unsaturated comonomers containing an acid group of pendant hydroxyl groups with the halides of these comonomers, of hydroxyl groups containing double bonds containing isocyanates such as vinyl isocyanate, methacryloyl isocyanate and / or 1- (1-isocyanato-1-methylethyl) -3- (1-methylethenyl) benzene (TMI® CYTEC) or of pendant isocyanate groups with the above-described comonomers containing hydroxyl groups.
  • TMI® CYTEC 1- (1-isocyanato-1-methylethyl) -3- (1
  • the content of the dimensionally stable particles on the binders described above may vary widely.
  • the thermally externally crosslinking or thermally externally crosslinking and curable with actinic radiation slurries according to the invention it is preferably from 5 to 80, preferably 6 to 75, more preferably 7 to 70, most preferably 8 to 65 and especially 9 to 60 wt.
  • the content can be up to 100
  • the dimensionally stable particles of the thermal or thermal and actinic radiation curable slurries of the invention may contain crosslinking agents having complementary reactive functional groups for thermal crosslinking and / or reactive functional groups having at least one bond activatable with actinic radiation.
  • Crosslinking agents which are suitable are all crosslinking agents customary in the field of light-stable clearcoats. Examples of suitable crosslinking agents are
  • Carboxyl-containing compounds or resins as described for example in the patent DE 196 52 813 A1 or 198 41 408 A1, in particular 1, 12-dodecanedioic acid,
  • Epoxy-containing compounds or resins as described, for example, in the patents EP 0 299 420 A1, DE 22 14 650 B1, DE 27 49 576 B1, US 4,091,048 A or US Pat. No. 3,781,379 A,
  • Tris (alkoxycarbonylamino) triazines such as 0604922 A are described in the patents US 4939213 A1 US 5084541 A, US 5288865 A or EP patent application,
  • beta-hydroxyalkylamides such as N, N, N ', N'-tetrakis (2-hydroxyethyl) adipamide or N, N, N', N'-tetrakis (2-hydroxypropyl) adipamide.
  • crosslinking agents described above may be used singly or as a mixture of at least two crosslinking agents.
  • the blocked polyisocyanates and / or tris (alkoxycarbonylamino) triazines, in particular the blocked polyisocyanates have particular advantages and are therefore used with particular preference.
  • the content of the dimensionally stable particles of the novel slurry on the crosslinking agents can also vary widely and depends primarily on the functionality and amount of the binder on the one hand and the functionality of the crosslinking agent on the other. Preferably, it is 10 to 95, preferably 12 to 94, more preferably 14 to 93, most preferably 16 to 92 and in particular 18 to 90 wt .-%, each based on the solids of the slurry of the invention.
  • the dimensionally stable particles of the slurry according to the invention may contain, in addition to the essential components described above, additives such as are commonly used in clearcoats. It is essential that these additives do not significantly lower the glass transition temperature Tg of the binders.
  • suitable additives are polymers other than the binders and crosslinking agents described above, crosslinking catalysts, defoamers, adhesion promoters, additives for improving surface wetting, surface-improving additives, matting agents, light stabilizers, corrosion inhibitors, biocides, flame retardants or polymerization inhibitors, in particular photoinhibitors, as described in the book "Lackadditive” by Johan Bielemann, Wiley-VCH, Weinheim, New York, 1998.
  • the dimensionally stable particles may contain other than the binders described above, curable with actinic radiation components as additives, if inventive slurry should be curable thermally and with actinic radiation or with actinic radiation alone.
  • reactive diluents curable with actinic radiation such as those described in Römpp Lexikon Lacke and Druckmaschine, Georg Thieme Verlag, Stuttgart, New York, 1998, on page 491 under the heading "Reactive Thinner”; or to
  • the slurry of the invention may also contain additives in the aqueous phase.
  • nonionic thickeners examples include hydroxyethyl cellulose and polyvinyl alcohols. So-called nonionic associative thickeners are also available on the market in a wide variety of choices. They usually consist of water-dilutable polyurethanes, which are reaction products of water-soluble polyether diols, aliphatic diisocyanates and monofunctional hydroxyl compounds with an organophilic radical.
  • ionic thickeners usually contain anionic groups and are based in particular on special polyacrylate resins having acid groups which may be partially or completely neutralized.
  • suitable thickeners to be used according to the invention are from the textbook “Lackadditive” by Johan Bielemann, Wiley-VCH, Weinheim, New York, 1998, pages 31 to 65, or the German patent application DE 199 08 018 AI. Page 13, line 18, to page 14, line 48, known.
  • a thickener in particular a nonionic thickener, is sufficient to set the desired pseudoplastic behavior.
  • the amount of thickener to be added and, if two different thickeners are used, the ratio of ionic to nonionic thickener depend on the desired viscosity of the slurry of the invention, which in turn are dictated by the required settling stability and the special requirements of the spray application.
  • the person skilled in the art can therefore determine the amount of thickener and, if appropriate, the ratio of thickener types to one another based on simple considerations, if appropriate with the aid of preliminary tests.
  • the aqueous phase of the slurry of the invention may further contain crosslinkable flow control agents in the film.
  • suitable constituents of this type are thermally curable reactive diluents such as positionally isomeric diethyloctanediols or hydroxyl-containing hyperbranched compounds or dendrimers as described in German patent applications DE 198 05 421 A1, DE 198 09 643 A1 or DE 19840405 A1.
  • the slurry according to the invention may contain in its aqueous phase at least one, in particular one, water-soluble salt, preferably in an amount of from 0.1 to 50 mmol per 1,000 g of water present in the slurry according to the invention.
  • the salt is residue-free or decomposes essentially residue-free. This means that it does not form any residues or residues in its decomposition in an amount which does not cause any disadvantageous technical effects in the clearcoats of the invention.
  • the salt may be decomposable by means of heat and / or actinic radiation. Preferably, it is thermally decomposable. It is preferably decomposable under the conditions of curing of the clearcoat films of the invention produced from the slurries. According to the invention, it is advantageous if the salt is decomposable at temperatures above 100 ° C.
  • the decomposition of the salt is preferably complete at 250, preferably 200, more preferably 190 and especially 180 ° C.
  • the decomposition products may be volatile elements, neutral organic or inorganic hydrogen compounds, organic and inorganic bases, organic and inorganic acids or oxides.
  • Examples of volatile elements are phosphorus, sulfur, nitrogen or oxygen, in particular nitrogen.
  • Examples of neutral organic and inorganic hydrogen compounds are water or hydrocarbons, especially water.
  • organic and inorganic bases are ammonia, methylamine, dimethylamine or trimethylamine, especially ammonia.
  • organic and inorganic acids are formic acid, acetic acid, propionic acid, oxalic acid, citric acid, tartaric acid, hydrochloric acid, hydrogen bromide, phosphoric acid, phosphorous acid, amidosulfonic acid, sulfuric acid, sulfurous acid, thiosulfuric acid, HSCN or hydrogen sulfide, especially acetic acid.
  • oxides are carbon dioxide, sulfur dioxide, sulfur trioxide or phosphorus oxides, in particular carbon dioxide.
  • a salt is selected whose decomposition products are not or only slightly toxic and / or non-corrosive or only slightly corrosive. Preference is given to choosing a salt which forms as decomposition products water, nitrogen, carbon dioxide, ammonia and organic acids.
  • the salt is particularly preferably selected from the group of ammonium salts, very particularly preferably from the group consisting of salts of ammonia and of organic amines with organic and inorganic acids.
  • ammonium salt is selected from the group consisting of ammonium carbonate, ammonium thiocyanate, ammonium sulfamate,
  • Ammonium hydrogen oxalate monohydrate, diammonium oxalate monohydrate, ammonium citrate and ammonium tartrate are ammonium hydrogen oxalate monohydrate, diammonium oxalate monohydrate, ammonium citrate and ammonium tartrate. Of these, in turn, ammonium carbonate and
  • Ammonium acetate very particularly advantageous and therefore very particularly preferably used according to the invention.
  • the slurry according to the invention is completely or substantially free of organic solvents.
  • “Completely free” means that the content of the inventive slurry of organic solvents is below the detection limits of the customary and known methods of qualitative and quantitative detection of organic solvents.
  • “Substantially free” means that the content of the slurries according to the invention of organic solvents is so low that it does not adversely affect the performance properties of the slurry.
  • the content in each case based on the slurry of the invention, ⁇ 5 wt .-%, preferably ⁇ 2.5 wt .-% and in particular ⁇ 1 wt .-%.
  • the slurry according to the invention is preferably prepared by the secondary dispersion process known from German Patent Application DE 199 08 018 A1, German Patent DE 198 41 842 C2 or German Patent Application DE 100 55 464 A1.
  • the ionically stabilizable binders and the crosslinking agents and optionally the additives are mixed in organic solution and dispersed together with the aid of neutralizing agents in water. Then it is with
  • the oil-in-water emulsion may also be prepared directly by melt emulsification of the binders and crosslinking agents and optionally the additives in water.
  • the wetting agents to be used according to the invention are added to the organic solution and / or the water before or during the emulsification. Preferably, they are added to the organic solution.
  • the solvent-containing emulsion thus obtained is subsequently freed of solvents by azeotropic distillation.
  • the removal-solvent at a distillation temperature below 7O 0 C, preferably below 5O 0 C and distilled in particular below 40 0C.
  • the distillation pressure is chosen so that this temperature range is maintained at higher boiling solvents.
  • the azeotropic distillation can be accomplished by stirring the emulsion at room temperature in an open vessel for several days.
  • the solvent-containing emulsion is freed from the solvents by vacuum distillation.
  • the evaporated or distilled off amount of water and solvents are replaced by water to avoid high viscosities.
  • the addition of the water can be done before, after or during the evaporation or distillation by adding in portions.
  • the glass transition temperature Tg of the dispersed particles increases, and instead of the previous solvent-containing emulsion, a dispersion, i. the slurry of the invention, from.
  • the salts to be used according to the invention can be introduced in different ways into the slurries or their precursors according to the invention.
  • the salts can be added to customary and known clearcoat slurries, resulting in the slurries according to the invention. They can also be added to the organic solution of constituents of the powder slurry according to the invention. Preferably, they are dissolved in the water before emulsifying the organic solution.
  • the particles of the slurry according to the invention are mechanically comminuted in the wet state, which is also referred to as wet milling.
  • Conditions are preferably used in this case that the temperature of the material to be ground does not exceed 70, preferably 60 and in particular 50 ° C.
  • the specific energy input during the milling process is preferably 10 to 1000, preferably 15 to 750 and in particular 20 to 500 Wh / g.
  • suitable devices which produce low shear fields are customary and known stirred tanks, gap homogenizers, microfluidizers or dissolvers.
  • Examples of suitable devices which produce high shear fields are conventional and known stirred mills or inline dissolvers.
  • the devices that produce high shear fields are used.
  • the agitator mills according to the invention are particularly advantageous and are therefore used with very particular preference.
  • the slurry according to the invention is fed by means of suitable devices, such as pumps, in particular gear pumps, to the devices described above and driven in a circle over this until the desired particle size is reached.
  • the slurry of the invention advantageously has a solids content of 10 to 60 wt .-%, in particular from 20 to 50 wt .-%, on.
  • the slurry of the invention is filtered before use.
  • the usual and known filtration devices and filters are used, as they come into consideration for the filtration of the known clearcoat slurries.
  • the mesh size of the filter can vary widely and depends primarily on the particle size and the particle size distribution of the particles of the slurry according to the invention. The person skilled in the art can therefore easily determine the suitable filters on the basis of this physical parameter. Examples of suitable filters are monofilament area filters or bag filters. These are available on the market under the brands Pong® or Cuno®.
  • bag filters are used with the mesh sizes 25 to 50 microns, for example, Pong® 25 to Pong® 50th
  • the slurry of the invention is applied to the substrate to be coated.
  • the application can be carried out by the usual and known methods, which is a further particular advantage of the slurry according to the invention.
  • the slurry according to the invention dries without problems and shows filming at the processing temperature, generally at room temperature.
  • the slurry applied as a wet layer ventilates at room temperature or slightly elevated temperatures with release of water, wherein the particles contained therein change their original shape and flow together. As a result, the tendency to "mudcracking" is extremely low.
  • the now largely anhydrous layer is crosslinked.
  • Step heating program or a so-called AufMaprampe is driven.
  • the present cross-linking temperature is between 120 and 16O 0 C.
  • the corresponding burn-in time is between 20 and 60 minutes.
  • the thermal curing is supplemented by curing with actinic radiation, the customary and known
  • Curing the actinic radiation curable inventive slurry can be applied.
  • the resulting clearcoat has excellent performance properties. It adheres firmly to all common and familiar basecoats or to substrates such as metal, glass, wood, ceramics, stone, concrete or plastic. It is of high gloss, smooth, scratch-resistant, weather-resistant, chemically stable and also in high layer thicknesses free of disturbances, such as stress cracks or digesters. When loaded with moisture, it no longer shows any whitening. In addition, it is free from micro-noise and shows no disturbing optical effects, such as a metallic effect -like starry sky.
  • the slurry according to the invention has a very good filterability with a very good gear pump passability.
  • the dimensionally stable particles of the slurry according to the invention already have an advantageously narrow particle size distribution immediately after their preparation, which does not change over time, or the change is so marginal that the advantageous performance properties of the slurry according to the invention are not affected ,
  • the slurry of the invention is excellent for the automotive OEM, automotive refinishing, painting of buildings in the interior and exterior, the painting of doors, windows and furniture and industrial coating, including coil coating, container coating, the painting of small parts , the impregnation and / or coating of electrical components or the painting of white goods, suitable.
  • it is mainly used for the production of clearcoats in the context of color and / or effect multi-layer coatings, according to the usual and known wet-in-wet process of basecoats and the slurry of the invention are prepared.
  • the slurry of the present invention can be easily combined with numerous basecoats, especially waterborne basecoats, without problems such as cracking, lack of wettability, and poor intercoat adhesion.
  • the slurry according to the invention can also be used as an adhesive for the production of adhesive layers and as a sealant for the production of seals, in particular in the abovementioned technical fields.
  • the Reaktio ⁇ smischung was allowed to react for 3 h at 78 0 C again. Subsequently, the volatiles were removed by vacuum distillation until a solids content of 70 wt .-% was set. Thereafter, the resin solution was discharged. It had a viscosity of 7.0 to 10.0 dPas (solid resin 60 percent XyIoI at 23 0 C). The acid number was 9.0 to 1, 0 and the hydroxyl number at 110 mg KOH / g of solid resin.
  • the resulting solution of the blocked polyisocyanate had a solids content of 81 wt .-% (1 h at 130 0 C) and a viscosity of 3.4 dPas (70% in methyl ethyl ketone; cone and plate viscometer at 23 ° C) ,
  • the resulting aqueous emulsion was diluted with 739 parts by weight of deionized water. Thereafter, it was removed on a rotary evaporator under vacuum, the same amount of a mixture of volatile organic solvents and water until the solids content was 37 wt .-% (1 h at 130 0 C).
  • the resulting clearcoat slurry had a pronounced pseudoplasticity.
  • the particle size distribution measured by the laser diffraction method was as follows:
  • the particle size distribution did not change over time, d. h., The clearcoat slurry showed no signs of aging.
  • the clearcoat slurry was very shear stable, which could be demonstrated by the gear pump test.
  • a laboratory apparatus was used in which the clearcoat slurry was subjected to a shear stress by pumping in a circle. 500 g of the clearcoat slurry were introduced into a 1 liter storage tank. Subsequently, it was pumped through a 80 cm long plastic tube with an inner diameter of 0.5 cm at a capacity of 600 ml / min at a pressure of 5 bar five times in a circle. The promotion took place by means of a gear pump (company Barmag, 6 ccm).
  • the clearcoat slurry remained very easy to filter even after the shear load.
  • test panels steel sheets were used, which had been coated with a conventional and known, cathodically deposited and baked electrocoating.
  • a layer of a customary and known water filler from BASF Coatings AG a layer of a customary and known, black aqueous basecoat from BASF Coatings AG, wet-in-wet was applied to the electrodeposition coatings. After their application, the layers were each pre-dried at 80 ° C. for 10 minutes.
  • the unloaded, filtered clearcoat slurry in wedge form was applied to the test panels. Subsequently, the resulting clearcoat slurry layer was baked together with the pre-dried water filler layer and the predried aqueous basecoat layer at 150 ° C. for 23 minutes.
  • the dry layer thickness of the resulting clearcoat was 20 to 70 ⁇ m. Due to the application to the vertical test sheets, an edge bead of a dry film thickness of 140 ⁇ m was formed on the lower edge of the part.
  • the clearcoats of the first or second series were completely equivalent in terms of their performance properties. They have excellent flow, gloss, chemical resistance and scratch resistance. They were free of agglomerates, specks, micro-disturbances (starry sky), blighting and craters in the area and at the edge.

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Abstract

L'invention concerne l'utilisation d'agents mouillants sélectionnés dans le groupe rassemblant des alcools gras alcoxylés comportant entre 8 et 15 atomes de carbone dans le groupe alkyle et, en moyenne statistique, entre 3 et 19 groupes d'oxaalkanediyle dans la molécule, dans des suspensions de vernis clair à viscosité intrinsèque. Cette invention concerne également une suspension de vernis clair à viscosité intrinsèque contenant des particules solides et/ou très visqueuses qui présentent une stabilité dimensionnelle dans des conditions de stockage et d'utilisation, et une répartition granulométrique monomode (D) mesurée par la technique de la diffraction laser : D (v, 0,1 ) = 0,8 à 1,2 µm ; D (v, 0,5) = 1,5 à 2,5 µm ; D (v, 0,9) = 2,5 à 3,6 µm, avec une étendue = {[D (v, 0,9)] - [D (v, 0,1 )]}/[D (v, 0,5)] = 0,8 à 1,5. La présente invention se rapporte en outre à un procédé de production et à l'utilisation de cette suspension de vernis clair à viscosité intrinsèque.
PCT/EP2006/008457 2005-09-01 2006-08-29 Utilisation d'alcools gras alcoxyles dans des suspensions de vernis clair a viscosite intrinseque, suspension de vernis clair a viscosite intrinseque, et procede de production et utilisation de cette suspension de vernis clair a viscosite intrinseque WO2007025722A2 (fr)

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DE102005041380.3 2005-09-01
DE200510041380 DE102005041380A1 (de) 2005-09-01 2005-09-01 Verwendung von alkoxylierten Fettalkoholen in strukturviskosen Klarlack-Slurries, strukturviskose Klarlack-Slurry, Verfahren zu ihrer Herstellung und ihre Verwendung

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WO2008063829A1 (fr) * 2006-11-21 2008-05-29 Basf Se Composition de revêtement présentant une faible teneur en composés organiques volatils
US8431639B2 (en) 2007-11-08 2013-04-30 Basf Corporation Wetting additive and composition including the same

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DE102008064254A1 (de) * 2008-12-20 2010-06-24 Basf Coatings Ag Wässriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung

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WO2008063829A1 (fr) * 2006-11-21 2008-05-29 Basf Se Composition de revêtement présentant une faible teneur en composés organiques volatils
US8119717B2 (en) 2006-11-21 2012-02-21 Basf Corporation Coating composition having a low volatile organic compound content
US8431639B2 (en) 2007-11-08 2013-04-30 Basf Corporation Wetting additive and composition including the same

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