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
  • C08G18/3225—Polyamines
  • C08G18/3253—Polyamines being in latent form
  • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
• • 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
  • C08G18/2805—Compounds having only one group containing active hydrogen
  • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
  • C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether 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
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
  • C08G18/78—Nitrogen
  • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
  • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
  • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• • 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
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
  • C08K3/013—Fillers, pigments or reinforcing additives
• • 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
  • C08K3/00—Use of inorganic substances as compounding ingredients
  • C08K3/32—Phosphorus-containing compounds
• • 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
  • C08G2150/00—Compositions for coatings
  • C08G2150/90—Compositions for anticorrosive coatings
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31678—Of metal

Definitions

• the present invention relates to coating compositions comprising at least one isocyanate-containing compound, at least one hydroxyl-containing compound, at least one aldimine and / or ketimine, one or more fillers, one or more pigments, at least one solvent and optionally one or more additives.
• the invention also relates to processes for the preparation of these coating compositions, their use as automotive refinish paints, in vehicle, commercial vehicle (including wells, chassis), and agricultural and railroad equipment and machinery.
• the coating compositions according to the invention are preferably used as primer (primer) with and without chemical pretreatment, such as iron or zinc phosphating, with and without mechanical pretreatment, such as sandblasting, grinding or the like.
• Coating compositions especially polyurethane coatings prepared by reaction of isocyanate-containing resins with polyol resins. These coatings are known to have a number of excellent properties including high durability and chemical resistance. Due to their good glamor qualities they are excellently suited for car repair, commercial vehicle and automotive repair applications as well as for technical applications. In comparison to aqueous compositions, they have significantly better drying times and improved corrosion protection.
• the polyol component due to the formation of hydrogen bonds and due to the molecular weight of the polymer backbone, provides the largest contribution to the overall viscosity of the coating, thereby limiting the freedom to incorporate other substances in the formulation and to meet the specification solids content specifications. The reduction in the molecular weight of the polyol ultimately results in slow network buildup unless significant amounts of energy are input.
• CX5NFIRMATION COPY Although the use of more solvents can reduce the overall viscosity of the coating and thus accelerate the network construction, the use of high amounts of solvents is of concern to the environment.
• coating compositions containing high levels of volatile organic compounds, particularly solvents (VOCs) do not meet the requirements of guidelines that specify the maximum level of VOCs. In the future, very low solvent contents or VOC contents of at most 280 g / l can be achieved.
• a coating composition comprising from 10 to 20% by weight of at least one isocyanate-containing compound, from 5 to 20% by weight of at least one hydroxyl-containing compound, from 5 to 25% by weight of at least one aldimine and / or ketimine, 2.5-60 %
• fillers, coloring pigments and anti-corrosive pigments wherein the filler or a calcium hydrogen phosphate is contained in a mass fraction of 1.0 to 20 wt .-%, each based on the total weight of the coating composition, and at least one solvent, wherein at least one silane compound of the general formula (I),
• R 1 for H; unsubstituted or at least monosubstituted alkyl; unsubstituted or at least monosubstituted heteroalkyl; unsubstituted or at least monosubstituted cycloalkyl or cycloalkenyl; unsubstituted or at least monosubstituted heterocycloalkyl or heterocycloalkenyl; unsubstituted or at least monosubstituted aryl or unsubstituted or at least monosubstituted - (alkylene) -aryl or - (alkenylene) -aryl;
• R 2 is unsubstituted or at least monosubstituted - (alkylene) -; unsubstituted or at least monosubstituted - (heteroalkylene) -; unsubstituted or at least monosubstituted - (arylene) -; unsubstituted or at least monosubstituted - (alkylene) - (arylene) - or unsubstituted or at least monosubstituted - (heteroalkylene) - (arylene) -;
• R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently H; unsubstituted or substituted alkyl or unsubstituted or substituted heteroalkyl;
• the coating compositions of the invention generally contain a solvent. Coating compositions according to the invention may also contain reactive diluents instead of the solvents, which may likewise lead to a reduction in the viscosity. These coating compositions adhere well to very well to aluminum, steel and / or multi-fabric substrates, have good weathering properties, provide good to very good corrosion protection, dry quickly and have good sandability.
• alkyl for the purposes of the present invention acyclic saturated hydrocarbon residues which can be branched or straight chained and unsubstituted or at least may be monosubstituted with as in the case of Ci- 12 alkyl 1 to 12 (ie, 1, 2, 3, 4 , 5, 6, 7, 8, 9, 10, 11 or 12) carbon atoms or with as in the case of C 1-6 -alkyl 1 to 6 (ie 1, 2, 3, 4, 5 or 6)
• Ci-1 2 alkyl radicals which may be unsubstituted or substituted one or more times, are for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl , 2-pentyl, 3-pentyl, iso-pentyl, neo-pentyl, n-hexyl, 2-hexyl, 3-hexyl, n-heptyl, n-octyl, -C (H) (C 2 H 5 ) 2 , -C (H) (nC 3 H 7 ) 2 and -CH 2 - CH 2 -C (H) (CH 3 ) - (CH 2 ) 3 -CH 3 .
• Suitable d- ⁇ -alkyl radicals are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, iso-pentyl , neo-pentyl, n-hexyl, 2-hexyl and 3-hexyl.
• multiply substituted alkyl radicals are meant those alkyl radicals which are monosubstituted, preferably triply or twice, at different or identical carbon atoms, for example, three times at the same carbon atom as in the case of -CF 3 or in various places as in the case of - (CHCl) - (CH 2 F). Multiple substitution can be with the same or different substituents.
• substituted alkyl radicals for example -CF 3 , -CF 2 H, -CFH 2 , - (CHz) -CN, - (CH 2 HCF 3 ), - (CH 2 ) - (CHF 2 ), - (CH 2 ) - (CH 2 F), - (CH 2 ) - (CH 2 ) -CN, - (CF 2 HCF 3 ) and - (CH 2 HCH 2 HCF 3 ).
• alkenyl in the context of the present invention comprises acyclic unsaturated hydrocarbon radicals which may be branched or straight-chained and unsubstituted or at least monosubstituted and have at least one double bond, preferably 1, 2 or 3 double bonds, as in the case of C 2 -12 alkenyl 2 to 12 (ie 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) carbon atoms or with as in the case of C 2, 6 alkenyl 2 to 6 (ie 2, 3, 4, 5 or 6) C atoms
• substituents are an alkenyl radical or have an alkenyl radical which is monosubstituted or polysubstituted, this may preferably be substituted by 1, if appropriate, 2, 3, 4 or 5, more preferably 1, 2 or 3, substituents independently selected from the group consisting of F, Cl, Br, I, -NO 2 , -CN, -OH, -SH, -NH 2 , -N (Ci -5
• Ci- 5 alkyl 2 groups where the above C- ⁇ - 5 alkyl radicals may be linear or branched and the abovementioned phenyl radicals preferably having 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of F, Cl, Br, I, -CN 1 -CF 3 , methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl and tert-butyl may be substituted. Particularly preferred substituents can be independently selected from the group consisting of F, Cl, Br, I, -NO 2 and -CN.
• heteroalkyl refers to an alkyl radical as described above in which one or more C atoms have each been replaced by a heteroatom independently selected from the group consisting of oxygen, sulfur and nitrogen (NH).
• Heteroalkyl radicals may preferably have 1, 2 or 3 heteroatom (s) independently of one another selected from the group consisting of oxygen, sulfur and nitrogen (NH) as chain member (s).
• the heteroatom is an oxygen or sulfur atom.
• the heteroatom is an oxygen atom.
• Heteroalkyl radicals may preferably be 2- to 12-membered, more preferably 2- to 6-membered.
• heteroalkyl radicals which may be unsubstituted or mono- or polysubstituted are -CH 2 -O-CH 3 , -CH 2 -OC 2 H 5 , -CH 2 -O-CH (CHa) 2 , -CH 2-OC (CHa) 3, -CH 2 -CH 2 -O-CH 3, -CH 2 -CH 2 -OC 2 H 5, -CH 2 -CH 2 -O- CH (CH 3) 2, -CH 2 -CH 2 -OC (CH 3 ) 3 , -CH 2 -S-CH 2 -O-CH 3 , -CH 2 -O-CH 2 -OC 2 H 5 , -CH 2 -O-CH 2 -O- CH (CH 3 ) 2 , -CH 2 -S-CH 2 -OC (CHs) 3 , -CH 2 -O-CH 2 -S-CH 3 , -CH 2 -O-CH 2 -SC 2
• Suitable substituted heteroalkyl radicals are - (CH 2 JO- (CF 3 ), - (CH 2 JO- (CHF 2 ), - (CH 2 JO- (CH 2 F), - (CF 2 ) -O- (CF 3 ) and - (CH 2 ) - (CH 2 ) - (CH 2 ) -O- (CF 3 ).
• cycloalkyl in the context of the present invention means a cyclic saturated hydrocarbon radical having preferably 3, 4, 5, 6, 7, 8 or 9 C atoms, particularly preferably 3, 4, 5, 6 or 7 C atoms. Atoms, most preferably having 5 or 6 carbon atoms, the remainder being unsubstituted or simple substituted or polysubstituted by identical or different substituents.
• Cs-g-cycloalkyl radicals which may be unsubstituted or monosubstituted or polysubstituted are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclononyl.
• Suitable 03.7-cycloalkyl radicals cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl may be mentioned.
• heterocycloalkyl in the context of the present invention means a cyclic saturated hydrocarbon radical having preferably 3, 4, 5, 6, 7, 8 or 9 C atoms, particularly preferably 3, 4, 5, 6 or 7 C atoms. Atoms, very particularly preferably having 5 or 6 C atoms, in which one or more C atoms have in each case been replaced by a heteroatom independently of one another selected from the group consisting of oxygen, sulfur and nitrogen (NH) Heterocycloalkyl radicals may preferably be 1 , 2 or 3 heteroatom (s) independently of one another selected from the group consisting of oxygen, sulfur and nitrogen (NH) as ring member (s).
• heteroatom is particularly preferably an oxygen or sulfur atom
• Heterocycloalkyl radical can be unsubstituted or monosubstituted or polysubstituted by identical or different substituents.
• Heterocycloalkyl radicals can preferably be 3- to 9-membered, in particular s is preferably 3- to 7-membered, very particularly preferably 5- to 7-membered.
• suitable 5- to 7-membered heterocycloalkyl radicals include tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyranyl, oxetanyl and (1,3) -dioxolan-2-yl.
• heterocycloalkenyl in the context of the present invention means a cyclic unsaturated hydrocarbon radical having preferably 4, 5, 6, 7, 8 or 9 C atoms, more preferably having 4, 5, 6 or 7 C atoms, very particularly preferably having 5 or 6 C atoms, which has at least one double bond, preferably a double bond, and in which one or more C atoms have each been replaced by a heteroatom independently selected from the group consisting of oxygen, sulfur and nitrogen (NH)
• Heterocycloalkenyl radicals may preferably have 1, 2 or 3 heteroatom (s) independently of one another selected from the group consisting of oxygen, sulfur and nitrogen (NH) as ring member (s).
• the heteroatom is an oxygen or sulfur atom.
• the heteroatom is an oxygen atom.
• a heterocycloalkenyl radical can be unsubstituted or monosubstituted or polysubstituted by identical or different substituents.
• Heterocycloalkenyl radicals may preferably be 4- to 9-membered, more preferably 4-7-membered, most preferably 5-7-membered.
• heterocycloalkenyl radicals or of suitable 5- to 7-membered heterocycloalkenyl radicals which may be unsubstituted or monosubstituted or polysubstituted are (2,3) -dihydrofuranyl, (2,5) -dihydrofuranyl, (2, 3) - dihydrothienyl, (2,5) -dihydrothienyl, (2,3) -dihydrooxazolyl, (4,5) -dihydrooxazolyl, (2,5) -dihydrooxazolyl and dihydropyranyl.
• Heterocycloalkyl radical, cycloalkenyl radical or heterocycloalkenyl radical or have such a radical which is monosubstituted or polysubstituted, this may preferably with optionally 1, 2, 3, 4 or 5, particularly preferably with optionally 1, 2 or 3, substituents independently selected from the group consisting of F 1 Cl, Br, I, -CN, -CF 3 , -OH 1 -NH 2 , -O-CF 3 , -SH, -Ods-alkyl, -O- Phenyl, -O-CH 2 -phenyl, - (CH 2 JOC 1, 5 -alkyl, -C 1-5 -alkyl, -C 2-5 -alkenyl, -C 2-5 -alkynyl, -C ( O ) -O-Ci.
• Ci -5 alkyl radicals may each be linear or branched and the phenyl radicals each unsubstituted or with 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, substituents independently selected from the group consisting of F, Cl, Br, I, -CN, -CF 3 , -OH, -NH 2 , -O-CF 3 , -SH, -O-Ci-.
• aryl means a monocyclic or polycyclic, preferably a monocyclic or bicyclic, aromatic hydrocarbon radical having preferably 6, 10 or 14 carbon atoms
• An aryl radical may be unsubstituted or monosubstituted or polysubstituted Examples of suitable aryl radicals which may be mentioned are phenyl, 1-naphthyl, 2-naphthyl and anthracenyl, and particularly preferably an aryl radical is a phenyl radical.
• arylene in the context of the present invention means a monocyclic or bicyclic, aromatic hydrocarbon radical having preferably 6 or 10 C atoms which is divalent, ie the radical has two open valences or bonding sites in the skeleton of the general formula I.
• An aryl radical can be unsubstituted or monosubstituted or polysubstituted by identical or different substituents.
• An arylene radical can be unsubstituted or monosubstituted or polysubstituted by identical or different substituents.
• a preferred arylene radical is phenylene.
• - (alkylene) - (arylene) -" and “- (heteroalkylene) - (arylene) - mean in the context of the present invention bivalent or divalent hydrocarbon radicals in which an open valency on the alkyl or heteroalkyl
• a - (alkylene) - (arylene) - or - (heteroalkylene) - (arylene) - may be unsubstituted or monosubstituted or polysubstituted by identical or different substituents.
• Suitable - (alkylene) - (arylene) radicals which may be unsubstituted or monosubstituted or polysubstituted are - (CH 2 ) -phenylene and - (CH 2 ) - (CH 2 ) -phenylene.
• d- may be linear or branched 5 alkyl radicals and the cyclic substituents or the cyclic residues of these substituents even with optionally 1, 2, 3, 4 or 5, preferably with optionally 1, 2, 3 or 4, substituents independently of one another selected from the group consisting of F, Cl, Br, I 1 -CN, -NO 2 , -OH, -SH, -NH 2 , -C ⁇ -alkyl, -OC 1-5 -alkyl, -CF 3 , -CHF 2 , -CH 2 F, -O-CF 3 , -O-CHF 2 and 0-CH 2 F may be substituted.
• the substituents each independently selected from the group consisting of F, Cl, Br, I, -CN, -NO 2 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 2-butyl , tert-butyl, -O-CH 3 , -O-C 2 H 5 , -O-C 3 H 7 , -OC (CH 3 ) 3 , -CF 3 , -CHF 2 and -CH 2 F.
• alkylene encompasses divalent acyclic saturated hydrocarbon chains which connect the hydrocarbon radical with the compound of the general formula I or with another substituent Alkylene chains can be branched or straight-chain and unsubstituted or at least monosubstituted with as in the case of Ci-1 2 -alkylene 1 to 12 (ie, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) C atoms, as in the case of Ci - 6 - Alkylene 1 to 6 (ie 1, 2, 3, 4, 5 or 6) carbon atoms or with as in the case of Ci -3 - alkylene 1 to 3 (ie, 1, 2 or 3) carbon atoms.
• Ci -5 alkylene groups such as - (CH 2) -, - (CH2) Z-, -C (H) (CH 3) -, - (CHz) 3 -, - (CH 2 J 4 - , - (CHz) 5 -, -C (CH 3 ) 2 -, -C (H) (CH 3 ) -, -C (H) (C (H) (CH 3 ) 2 ) - and C (C 2 H 5 ) (H) - called.
• alkenylene in the context of the present invention comprises acyclic unsaturated hydrocarbon chains which connect hydrocarbon radical with compound of general formula I or with another substituent.
• Alkenylene chains have at least one double bond, preferably 1, 2 or 3 double bonds, and may be branched or straight-chain and unsubstituted or at least monosubstituted with as in the case of C 2 -12 -alkenes 2 to 12 (ie 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12) C atoms, as in the case of C 2-6 alkenylene 2 to 6 (ie 2, 3, 4, 5 or 6) C- Atoms or with as in the case of C 2-3 - Alkenylene 2 to 3 (ie 2 or 3) C atoms.
• heteroalkylene refers to an alkylene chain as described above in which one or more C atoms have each been replaced by a heteroatom independently selected from the group consisting of oxygen, sulfur and nitrogen (NH).
• Heteroalkylene groups may preferably have 1, 2 or 3 heteroatom (s), more preferably a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen (NH) as a chain member (s).
• the heteroatom is an oxygen or
• heteroalkylene groups may preferably be 2- to 12-membered, particularly preferably 2- to 6-membered, very particularly preferably 2- or 3-membered.
• Heteroalkylene group or have such a group which is monosubstituted or polysubstituted, these may preferably with optionally 1, 2, 3, 4 or 5, particularly preferably with optionally 1, 2 or 3, substituents independently selected from Group consisting of F, Cl, Br, I, -NO 2 and -CN be substituted.
• the coating composition comprises from 12 to 20% by weight of polyisocyanate and from 8 to 18% by weight of polyol and from 8 to 25% of ketimine or aldimines or mixtures thereof.
• the coating composition according to the invention preferably contains from 30 to 60% by weight, preferably from 40 to 60% by weight, of one or more fillers, coloring pigments and anti-corrosive pigments.
• the filler or the anticorrosive pigmentation is not chromate-containing.
• the coating composition according to the invention contains calcium hydrogen phosphate in a mass fraction of 1 to 10 wt .-%, particularly preferably 1- 5 wt .-%.
• the coating composition according to the invention preferably contains from 0.1 to 3% by weight of at least one silane compound of the general formula (I).
• Phenyl or benzyl radical which is unsubstituted or having 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of F, Cl, Br, I, -CN, -NO 2 , methyl, ethyl, n Propyl, isopropyl, n-butyl, isobutyl, 2-butyl, tert-butyl, -O-CH 3) -O-C 2 H 5 , -O-C 3 H 7 , -OC (CH 3 ) 3 , - CF 3 , -CHF 2 and -CH 2 F is substituted;
• R 2 -Akenylen 5 radical represents a Ci- which is substituted consisting of F, Cl, Br, I, -NO 2, and -CN unsubstituted or optionally substituted with 1, 2 or 3 substituents independently selected from the group;
• R 1 for H an alkyl radical selected from the group consisting of methyl, ethyl, n -propyl, isopropyl, n -butyl, 2-butyl, isobutyl, tert -butyl, n -pentyl and n -hexyl, which is unsubstituted; or is a phenyl radical which is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently of one another selected from the group consisting of F, Cl, Br and methyl;
• R 2 is - (CH 2 ) -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, - (CH 2 ) 4 - or - (CH 2 ) 5 -;
• R 3 is -OR 6 or H
• R 4 is -OR 8 or H
• R 5 is -OR 10 or H; and R 6 , R 8 and R 10 , independently of one another, are each H or an alkyl radical selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl Butyl, n-pentyl and n-hexyl, which is unsubstituted.
• silane compounds of the general formula (I) in which R 1 is H; or is a phenyl radical which is unsubstituted or substituted by 1, 2, 3, 4 or 5 substituents independently of one another selected from the group consisting of F, Cl, Br and methyl; R 2 is - (CHz) 3 -; R 3 is -OR 6 ; R 4 is -OR 8 ; R 5 is -OR 10 ; and R 6 , R 8 and R 10 , independently of one another, each represent a methyl or ethyl radical.
• silane compounds of general formula (I) selected from the group consisting of
• 3-aminopropyltrimethoxysilane e.g. Commercially available as Geniosil GF 96 from Wackerchemie, 4-amino-3,3-dimethylbutyltrimethoxysilane commercially available as Silquest A-1637 from the company.
• Momentive and N-phenyl- ⁇ -aminopropyltrimethoxysilane for example, commercially available as Y-15085 (Silquest Y-9669) from the company Momentive.
• the calcium hydrogen phosphate preferably has a particle size of 1.0 to 10.0 ⁇ m, preferably 2.5 to 4.0 ⁇ m (measured with a Coulter Multisizer II). Using particles of this size results in particularly smooth surfaces.
• the coating composition is preferably a combination of at least one isocyanate-containing compound, at least one hydroxyl-containing compound, at least one ketimine, one or more fillers, coloring pigments and anticorrosion pigments, where a filler is calcium hydrogenphosphate, at least one solvent and at least one silane of the above.
• the coating composition particularly preferably contains 10 to 20% by weight of at least one isocyanate-containing compound, 5 to 20% by weight of at least one hydroxyl-containing compound, 5 to 25% by weight of at least one ketimine, and 30 to 60% by weight of one or a plurality of fillers, coloring pigments and anti-corrosive pigments, wherein as the or a filler calcium hydrogen phosphate in a mass fraction of 0.1 to 20 wt .-% is contained, and at least one compound of the above formula (I) in one Mass fraction of 0.1 to 5 wt .-%, each based on the total weight of the coating composition.
• the coating composition most preferably contains from 12 to 20% by weight of at least one isocyanate-containing compound, from 12 to 20% by weight of at least one hydroxyl-containing compound, from 8 to 18% by weight of at least one ketimine, and from 8 to 25% by weight of one or more fillers, coloring pigments and anticorrosive pigments, wherein as the or a filler calcium hydrogen phosphate is contained in a mass fraction of 1 to 10 wt .-%, at least one solvent, and at least one compound of the above formula (I) in a mass fraction of 0.1 to 3 wt .-%, each based on the total weight of the coating composition.
• polyisocyanates which are used as bases for the isocyanate group-containing compounds preferably used in accordance with the invention are preferably per se known substituted or unsubstituted aromatic, aliphatic, cycloaliphatic and / or heterocyclic polyisocyanates.
• the polyisocyanate or the isocyanate-containing compound preferably has an average NCO functionality of 2 to 6.
• polyisocyanates examples include: 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, diphenylmethane-4,4'-diisocyanate, diphenylmethane-2,4'-diisocyanate, p-phenylene diisocyanate, biphenyl diisocyanates, 3,3'-dimethyl-4 , 4'-diphenyl diisocyanate, tetramethylene-1,4-diisocyanate, hexamethylene-1,6-diisocyanate, 2,2,4-trimethylhexane-1,6-diisocyanate, isophorone diisocyanate, ethylene diisocyanate, 1,12-dodecane diisocyanate, cyclobutane-1, 3-diisocyanate, cyclohexane-1,4-diiso
• polyisocyanates are those obtained by oligomerization, trimerization, dimerization, urethane, biuret or allophanate formation of a polyisocyanate derived from a polyisocyanate or a mixture of these.
• the latter polyisocyanates have a low viscosity.
• Particularly preferred polyisocyanates are hexamethylene-1, 6-diisocyanate
• Very particularly preferred polyisocyanates are asymmetric trimers of
• Hexamethylene-1,6-diisocyanate are particularly low viscosity.
• the hydroxyl-containing compound used is preferably a low molecular weight polyol, an oligomeric polyol, a polymeric polyol or a mixture of these polyols.
• the hydroxyl-containing compounds preferably have viscosities ⁇ 4500 m "Pa" s at 23 ° C measured in accordance with DIN EN ISO 3219 / A.3 and glass transition temperatures of ⁇ 0 0 C measured by DSC.
• the hydroxyl number of the polyols is 5 to 350, preferably 8 to 200 mg KOH / g substance.
• the hydroxyl number indicates how much mg of potassium hydroxide is equivalent to the amount of acetic acid bound by 1 g of substance in the acetylation.
• the sample is boiled in the determination with acetic anhydride-pyridine and the resulting acid is titrated with potassium hydroxide solution (DIN 53240-2).
• the acid number indicates the number of mg of potassium hydroxide used to neutralize 1 g of the respective hydroxyl-containing compound (DIN EN ISO 2114).
• mass-average molecular weights Mw of the polyols are between 650 and 20,000 daltons, more preferably between 750 and 10,000 daltons, in each case measured by gel permeation chromatography (GPC) against a polystyrene standard.
• the hydroxyl-containing compound is preferably a polyol having ether and / or ester groups. Preferably, this polyol is branched.
• polyester polyols are further (eg Ullmanns Enzyklopadie der ischen Chemie, 4th Edition, Volume 19, pp 62-65) are difunctional alcohols such as ethylene glycol, 1, 2 and 1, 3-propylene glycol , 1, 3-, 1, 4-, 2,3-butanediol, 1,6-hexanediol, neopentyl glycol, trimethylhexanediol, triethylene glycol, tetraethylene glycol, hydrogenated bisphenols, trimethylpentanediol, diethylenediglycol, dipropylene-diglycol, 1,4-cyclohexanediol, 1, 4
• Cyclohexanedimethanol and difunctional carboxylic acids or their anhydrides such as adipic acid, phthalic acid (anhydride), isophthalic acid, maleic acid (anhydride), terephthalic acid, tetrahydrophthalic acid (anhydride), hexahydrophthalic acid (anhydride), succinic acid (anhydride), fumaric acid, azelaic acid, dimer fatty acids.
• Monocarboxylic acids such as benzoic acid, 2-ethylhexanoic acid, oleic acid, soybean oil fatty acid, stearin fatty acid, peanut oil fatty acid, linseed fatty acid, nonanoic acid, cyclohexane monocarboxylic acid, isononanoic acid, sorbic acid, conjuene fatty acid, higher functional carboxylic acids or alcohols such as trimellitic acid (anhydride), butanetetracarboxylic acid are also suitable for use in minor amounts , Trimer fatty acids,
• the proportion by weight of the hydroxyl-containing fatty acid based on the hydroxyl contents of the hydroxyl-containing compounds is preferably more than 60, more preferably more than 80 and particularly preferably more than 120%.
• lactone-based polyesterdiols which are homopolymers or copolymers of lactones, preferably addition products of lactones such as terminal hydroxyl groups.
• suitable polyol components are polyether polyols. They are z. B. by polymerization of ethylene oxide, propylene oxide and / or tetrahydrofuran with itself, z. B. in the presence of BF 3 or basic catalysts or by addition of these compounds optionally also in admixture or in succession, to starter components with reactive hydrogen atoms, such as alcohols, amines, amino alcohols or water.
• Corresponding polyether polyols that can be used in the claimed invention are also in fat science technology / fat science
• Preferred examples of commercial hydroxyl-containing compounds are Desmophen 1150, Sovermol 818, Sovermol 805, Sovermol 750, Caspol 5009, Caspol 1938 and Caspol 1842.
• the aldimine or ketimine used is the reaction product of the reaction of isophoronediamine with a corresponding aldehyde or ketone.
• These reaction products have a low viscosity and are therefore suitable for use in the coating compositions according to the invention.
• aldimines and ketimines can be prepared as described in March, Advanced Organic Chemistry, Reactions, Mechanisms and Structure Third ed. P. 797, John Wiley & Sons. Further description can be found in EP 0686654
• the coating compositions according to the invention preferably comprise ⁇ 540 g / l of volatile organic compounds (VOC). Most preferably, the coating compositions comprise ⁇ 280 g / L VOC. Due to their low VOC content, they only lead to a small extent to an environmental impact.
• Particularly suitable solvents for the novel coating compositions are those which are chemically inert in the coating composition with respect to hydroxyl-containing compounds and compounds containing isocyanate groups and which do not react with hydroxyl-containing compounds and compounds containing isocyanate groups even in the curing of the sweeping agent.
• solvents examples include aliphatic and / or aromatic hydrocarbons such as toluene, xylene, solvent naphtha, Solvesso 100 or hydrosol ® (Fa. Aral), ketones such as acetone, methyl ethyl ketone or methyl amyl ketone, esters such as ethyl acetate, butyl acetate, pentyl acetate or ethyl ethoxypropionate, ether or mixtures of the aforementioned solvents. Particularly preferred is butyl acetate as the solvent.
• the aprotic solvents or solvent mixtures preferably have a water content of not more than 1% by weight, more preferably not more than 0.5% by weight, based on the solvent.
• the coating composition of the invention may comprise at least one conventional and well-known paint additive in effective amounts, i. in amounts preferably up to 30 wt .-%, more preferably up to 25 wt .-% and most preferably up to 20 wt .-%, each based on the total weight of the coating composition.
• paint additives examples include: in particular UV absorbers; in particular light stabilizers such as HALS compounds, benzotriazoles or
• Reactive thinner as are well known in the art, which are preferably inert to the -Si (OR) 3 groups.
• wetting agents such as siloxanes, fluorine-containing compounds, carboxylic acid monoesters,
• Phosphoric acid esters polyacrylic acids and their copolymers or
• Adhesion promoters such as tricyclodecanedimethanol; Leveling agents; dispersant; settling agents; Pigment stabilizers; - film-forming aids such as cellulose derivatives;
• Fillers such as nanoparticles based on silica, alumina or zirconia; in addition, reference is made to the Römpp Lexikon "Paints and Printing Inks” Georg Thieme Verlag, Stuttgart, 1998, pages 250 to 252; - Fillers such as reinforcing fillers such.
• pyrogenic adenosine triphosphate
• Silicic acid precipitated silica and calcium carbonate
• Fillers such as zinc phosphate
• Rheology controlling additives such as the additives known from the patents WO 94/22968, EP-A-0 276 501, EP-A-0 249 201 or WO 97/12945; crosslinked polymeric microparticles, as described, for example, in EP-A-008
• inorganic phyllosilicates such as aluminum-magnesium silicates, sodium magnesium and sodium magnesium fluorine lithium phyllosilicates of the montmorillonite type
• Silicas such as aerosils
• synthetic polymers having ionic and / or associative groups such as polyvinyl alcohol, poly (meth) acrylamide, poly (meth) acrylic acid
• the coating composition of the invention may contain coloring pigments and anti-corrosive pigments.
• the pigments used for this purpose are known to the person skilled in the art.
• Coloring pigments are, for example, white pigments such as titanium dioxide, zinc oxide, zinc sulfide, lithopone and barium sulfate and black pigments such as carbon black, inorganic spinels and organic black pigments.
• Coloring pigments are, for example, also colored pigments such as inorganic colored pigments (iron oxide, lead molybdate, bismuth vanadate, cyane iron blue, ultramarine) and organic colored pigments (Azo pigments, metal-core pigments, triphenylmethane pigments, indigoid pigments, isoindollines, isoindolinones, anthraquinones, quinacridones and perylene).
• inorganic colored pigments iron oxide, lead molybdate, bismuth vanadate, cyane iron blue, ultramarine
• organic colored pigments Azo pigments, metal-core pigments, triphenylmethane pigments, indigoid pigments, isoindollines, isoindolinones, anthraquinones, quinacridones and perylene).
• the invention also provides a process for the preparation of a composition according to the invention, in which a composition comprising the at least one hydroxyl-containing compound is mixed with a composition comprising at least one isocyanate group-containing compound.
• a further composition comprising at least one aldimine and / or ketimine is mixed in with this mixing.
• the composition comprising at least one hydroxyl-containing compound preferably also contains the additive (s).
• at least one silane compound of the general formula (I) is mixed.
• the silane component according to the formula (I) is added to the filler and pigment-containing component or the reactive diluent-containing component. This is preferably done during paint completion with stirring or a multi-component mixing plant.
• the mixing is preferably carried out at temperatures between 10 and 30 0 C, more preferably at temperatures between 15 and 25 ° C.
• the invention further relates to the use of the coating compositions according to the invention as a paint in the car repair sector, in vehicle, commercial vehicle (also troughs, chassis) and agricultural machinery and railroads.
• the coating compositions according to the invention are preferably used as primer (primer) with and without chemical pretreatment, such as iron or zinc phosphating, with and without mechanical pretreatment, such as sandblasting, grinding or the like.
• primer primer
• chemical pretreatment such as iron or zinc phosphating
• mechanical pretreatment such as sandblasting, grinding or the like.
• the coating compositions of the invention can be used both as a primer under a basecoat and a clearcoat film as well as under a single-coat topcoat.
• Further preferred is the use of the coating compositions according to the invention as a primer on aluminum, steel, plastics and multi-substance substrates, ie Substrates made of different materials.
• multi-substance substrates are, in particular in the automotive repair sector, old coatings with pass through points.
• undefined metallic substrates (Durchschliffstelle) meet on undefined polymeric substrates (old paint eg from electrocoating, primer, basecoat and clearcoat).
• undefined polymeric substrates old paint eg from electrocoating, primer, basecoat and clearcoat.
• Particularly preferred is the use on aluminum or a multi-substance substrate.
• the invention likewise provides a coated substrate producible by coating a substrate with a coating composition according to the invention and curing the coating.
• the coated substrate is preferably coated with the coating composition as a primer under a basecoat and a clearcoat or under a single-coat topcoat.
• the substrate is preferably aluminum, steel or plastic or a multi-substance substrate. Particularly preferably, the substrate is aluminum or a multi-substance substrate.
• a coating composition is prepared by mixing 200 g of component 1, 47.4 g of component 3 and 60.1 g of component 2, to which 2.1 g each of silanes 1 to 5 have been added. Let us prefer to add the silane to component 1 before the completion.
• Example 1 Silane 1 Geniosil GF 96® 3-aminopropyltrimethoxysilane
• Example 2 Silane 2 Silquest Y-9669® N-phenyl-Y-aminopropyltrimethoxysilane
• the resulting coating composition is used as primer filler on steel (CRS panels for body panel No. 18 from Meier & Co.) and aluminum
• the cross-cut test is carried out in accordance with DIN ISO 2409.
• Salt spray test SS Specification: DIN 50 021 -SS
• Test chamber temperature 35 ⁇ 2 0 C continuously
• Test cycle Spraying of aqueous NaCl solution
• Tester Corrosion testers according to DIN 50 021: SL 2000 and SL 2000 from Liebisch
• Test chamber temperature 35 ⁇ 2 0 C continuously
• Test cycle Spraying with aqueous NaCl solution, acidic

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• 2008
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