[go: up one dir, main page]

EP1278791A1 - Substances de revetement, substances adhesives et masses d'etancheite a plusieurs constituants, ainsi que leur utilisation - Google Patents

Substances de revetement, substances adhesives et masses d'etancheite a plusieurs constituants, ainsi que leur utilisation

Info

Publication number
EP1278791A1
EP1278791A1 EP01933891A EP01933891A EP1278791A1 EP 1278791 A1 EP1278791 A1 EP 1278791A1 EP 01933891 A EP01933891 A EP 01933891A EP 01933891 A EP01933891 A EP 01933891A EP 1278791 A1 EP1278791 A1 EP 1278791A1
Authority
EP
European Patent Office
Prior art keywords
meth
isocyanate
adhesives
basecoat
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01933891A
Other languages
German (de)
English (en)
Inventor
Hubert Baumgart
Heinz-Peter Rink
Simone Bitter
Edeltraud Hagemeister
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Coatings GmbH
Original Assignee
BASF Coatings GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF Coatings GmbH filed Critical BASF Coatings GmbH
Publication of EP1278791A1 publication Critical patent/EP1278791A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • 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
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C08G18/2835—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds having less than 5 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S525/934—Powdered coating composition

Definitions

  • the present invention relates to new multi-component coating materials, adhesives and sealing compounds.
  • the present invention also relates to the use of the new multicomponent coating materials
  • the present invention further relates to the use of the new
  • Multi-component adhesives and sealants for the production of new adhesive layers and seals, especially in the fields of application listed above.
  • Two-component coating materials which - generally reactive components with isocyanate-reactive functional groups, customary and known polyisocyanates and adducts of diisocyanates and dioxolanes, dioxanes or oxazolidines, which have an isocyanate-reactive functional group, in a molar ratio of 1: 1, are known from German patent application DE 196 09 617 A 1 known.
  • the reactive components inter alia are hyroxy functional polymers with a hydroxyl group content of 0.1 to 20% by weight (corresponding to 33 to 660 mg KOH / g) ,
  • the zaMen average molecular weight of the polymers is preferably 1,000 to 100,000.
  • the polymers preferably contain more than 50% by weight of C 1 -C 2 -alkyl (meth) acrylate, vinyl aromatics with up to 20 carbon atoms, and vinyl esters with up to 20 carbon atoms Carboxylic acids, vinyl halides, non-aromatic hydrocarbons with 4 to 8 carbon atoms and 1 or 2 double bonds, unsaturated nitriles and their hybrids.
  • Polymers are preferred which contain up to 60% by weight of Ci-Cio-alkyl (meth) acrylates, styrene or mixtures thereof.
  • the polymers contain hydroxy-functional monomers, corresponding to the above hydroxyl group content, as well as other monomers such as unsaturated acids not specified, in particular carboxylic acids, acid anhydrides or acid amides.
  • the two-component coating materials known from DE 19609 617 A1 are not as widely applicable as would actually be desirable.
  • their service life i.e. the time within which they can be processed without any problems after the two components have been mixed and deliver perfect coatings can be extended even further.
  • Thermally curable coating materials based on binders and crosslinking agents containing hydroxyl groups and containing _functional groups reactive with hydroxyl groups are known from German published patent application DE 197 09 465 A1. After curing, they have a memory module E 'in the rubber-elastic range of at least 10 ⁇ .6 p a and. a loss factor tan ⁇ at 20 ° C of a maximum of 0.10, with the memory module E 'and Loss factor was measured with the dynamic mechanical thermal analysis on free films with a layer thickness of 40 + 10 ⁇ m.
  • Inter alia (meth) acrylate polymers which contain 4-hydroxybutyl methacrylate in copolymerized form are used as binders.
  • the coatings produced from the known coating materials are scratch-resistant and chemical-stable.
  • the level of scratch resistance that has already been achieved must be further improved for particularly demanding uses, for example in the series and refinishing of particularly high-quality automobiles of the upper class.
  • the known coatings should be easier to polish.
  • Methylpropane-1,3-diol-mono (meth) acrylate and its low molecular weight polymers are known from German patent application DE 32 34 045 A1.
  • the polymers are used to prepare photosensitive compositions which are used for imagewise exposure. It is not known whether they are also suitable for the production of multi-component coating materials, lifting materials or sealing compounds.
  • Multi-component coating materials adhesives and sealing compounds.
  • the multi-component coating materials provide scratch-resistant coatings, especially clear coats.
  • the object of the present invention is the known
  • Multi-component coating materials result, which are high Solids content with low viscosity and a long service life and coatings, in particular clearcoats and color and / or effect-giving solid-color top coats, basecoats and multi-layer coatings, which in addition to high hardness, flexibility and chemical resistance, also an excellent flow, a very good interlayer adhesion, an excellent overall optical impression, very good weather resistance, very high scratch resistance and very good polishability.
  • the object of the present invention to further develop the previously known two-component adhesives and sealants, so that new multicomponent adhesives and sealants with a high solids content at low viscosity and a long service life result, the adhesive layers of particularly high adhesive strength and seals of particularly high sealability also deliver to chemically aggressive substances.
  • (A) at least one (meth) acrylate copolymer having an OH number of 130 to 200, a glass transition temperature of -35 to + 60 ° C, a number average molecular weight of 1,000 to 5,000 daltons and a mass average molecular weight of 2,000 to 20,000 daltons contains copolymerized onto the (meth) acrylate copolymer (A) up to 90% by weight of hydroxyl-containing olefinically unsaturated monomers (a), of which
  • R 6 aliphatic radical having 1 to 30 carbon atoms, the carbon chains of which may be interrupted by one or more oxygen atoms, or aromatic group having 6 to 30 carbon atoms;
  • R 4 and R 5 independently of one another hydrogen atoms, isocyanate-reactive functional groups or radicals R 6 ;
  • a radical R 4 , R 5 or R 6 contains an isocyanate-reactive functional group or a radical R 4 or R 5 is an isocyanate-reactive functional group, the other radicals R 4 , R 5 or R 6 - if present - have no isocyanate-reactive functional groups;
  • coating materials for the sake of brevity, the new multi-component coating materials, adhesives and sealing compounds are referred to below as "coating materials, adhesives and sealing compounds according to the invention".
  • the new process for producing a color and or effect paint by application of a pigmented solid topcoat to a primed or unprimed substrate was found, in which the coating material of the invention is used as solid topcoat.
  • the new process for producing a color and / or effect multi-layer coating was carried out on a primed or unprimed substrate
  • a pigmented and a non-pigmented coating material according to the invention is used as the basecoat and as the clearcoat.
  • the coating materials, adhesives and sealants according to the invention are multi-component systems. This means that their highly reactive constituents are distributed over several components, which in themselves are stable in storage, and are only combined comparatively shortly before use.
  • “comparatively short” means a period of 1 minute to 24 hours
  • “shelf life” means that the component in question can be stored for at least 24 hours, preferably at least one week, without decomposition and / or premature crosslinking.
  • the constituents are preferably present in two components, the binders and, if appropriate, the reactive diluents in one component and the crosslinking agents in the other component.
  • the first component of the coating materials, adhesives and sealants according to the invention is the binder-containing component.
  • the essential component of the pharmaceutical-containing component to be used according to the invention is at least one binder. According to the invention, this is at least one (meth) acrylate copolymer (A) with special properties and a special composition.
  • the (meth) acrylate copolymer (A) contains, based in each case on (A), up to 90, preferably up to 88, preferably up to 86, particularly preferably up to 84, very particularly preferably up to 82 and in particular up to 80% by weight. -% polymerized in hydroxyl-containing olefinically unsaturated monomers (a), of which
  • % each based on the (meth) acrylate copolymer (A), represent other hydroxyl-containing olefinically unsaturated monomers.
  • 2-alkyl-propane-1,3-diol-mono (meth) acrylates are 2-methyl, 2-ethyl, 2-propyl, 2-isopropyl or 2-n-butyl-propane -1,3-diol-mono (meth) acrylate, of which 2-methyl-propane-1,3-diol-mono (meth) acrylate is particularly advantageous and is preferably used according to the invention.
  • Suitable other hydroxyl-containing olefinically unsaturated monomers (a2) are hydroxyalkyl esters of acrylic acid, methacrylic acid or another alpha, beta-ethylenically unsaturated carboxylic acid which (i) are derived from an alkylene glycol which is esterified with the acid, or (ii) by reaction the acid can be obtained with an alkylene oxide such as ethylene oxide or propylene oxide, in particular hydroxyalkyl esters of acrylic acid, methacrylic acid, crotonic acid or ethacrylic acid, in which the hydroxyalkyl group contains up to 20 carbon atoms, such as 2-hydroxyethyl, 3-hydroxypropyl, 3-hydroxybutyl methacrylate, ethacrylate or crotonate; 1,4-
  • Monomers (a2) are generally only used in minor amounts. In the context of the present invention, such amounts are subordinate amounts of higher-functional monomers (a2) to understand which do not lead to the crosslinking or gelling of the (meth) acrylate copolymers (A), unless they should be in the form of crosslinked microgel particles.
  • ethoxylated and / or propoxylated allyl alcohol which is sold by Arco Chemicals, or 2-hydroxyalkylallyl ether, in particular 2-hydroxyethylallyl ether, are suitable as monomers (a2). If used, they are preferably not used as sole monomers (a2), but in an amount of 0.1 to 10% by weight, based on the (meth) acrylate copolymer (A).
  • reaction products of acrylic acid and / or methacrylic acid with the glycidyl ester of a monocarboxylic acid with 5 to 18 carbon atoms per molecule in particular a Versatic® acid, or an equivalent amount of acrylic and / or methacrylic acid instead of the reaction products which then during or after the polymerization reaction with the glycidyl ester of a monocarboxylic acid with 5 to 18 carbon atoms per molecule branched in the alpha position, in particular one Versatic® acid (cf.Römpp Lexikon Lacke und Druckmaschinetician, Georg Thieme Verlag, Stuttgart, New York, 1998, »Versatic® acids«, pages 605 and 606).
  • the (meth) acrylate copolymers (A) contain further olefinically unsaturated monomers (a3) whose proportion of (A) is at least 10, preferably at least 12, preferably at least 14, particularly preferably at least 16, very particularly preferably at least 18 and in particular at least 20 % By weight.
  • Methoxyoligoglycol (meth) acrylate with a molecular weight Mn of preferably 550 daltons or other ethoxylated and / or propoxylated hydroxyl group-free (meth) acrylic acid derivatives further examples of suitable monomers (a2) of this type are from the published patent application DE 196 25 773 A1, column 3, line 65 to column 4, line 20, is known.
  • higher functional (meth) acrylic acid alkyl or cycloalkyl esters such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, butylene glycol, pentane-1, 5-diol, hexane-1, 6-diol, octahydro- 4,7-memano-1H-methane-dimethanol- or cyclohexane-1,2-, -1,3- or - 1,4-diol-di (meth) acrylate; Trimethylolpropane di- or tri (meth) acrylate; or pentaervithrite di, tri or tetra (meth) acrylate.
  • higher-functional monomers (a31) what has been said above for the monomers (a2) applies.
  • At least one acid group preferably a carboxyl group, ethylenically unsaturated monomers carrying per molecule or a mixture of these
  • Acrylic acid and / or methacrylic acid are particularly preferably used as component (a32). However, other ethylenically unsaturated carboxylic acids with up to 6 carbon atoms in the molecule can also be used.
  • Such acids are ethacrylic acid, crotonic acid, maleic acid, fumaric acid and itaconic acid. Furthermore, ethylenically unsaturated sulfonic or phosphonic acids or their partial esters can be used as component (a32) become.
  • Further monomers (a32) are maleic acid mono (meth) acryloyloxyethyl ester, succinic acid mono (meth) acryloyloxyethyl ester and phthalic acid mono (meth) acryloyloxyethyl ester as well as vinylbenzoic acid (all isomers), alpha-methylvinylbenzoic acid (all isomers) or vinylbenzenesulfonic acid (all isomers) , Further examples of monomers containing acid groups (a32) are known from published patent application DE 196 25 773 A1, column 2, line 58 to column 3, line 8, or from international patent application WO 98/49205, page 3, lines 23 to 34 ,
  • the branched monocarboxylic acids can be obtained by reacting formic acid or carbon monoxide and water with olefins in the presence of a liquid, strongly acidic catalyst; the olefins can be cracked products of paraffinic hydrocarbons, such as mineral oil fractions, and can contain both branched and straight-chain acyclic and / or cycloaliphatic olefins.
  • paraffinic hydrocarbons such as mineral oil fractions
  • a mixture of carboxylic acids is formed in which the carboxyl groups are predominantly located on a quaternary carbon atom.
  • olefinic starting materials are e.g. Propylene trimer, propylene tetramer and diisobutylene.
  • the vinyl esters can also be prepared from the acids in a manner known per se, e.g. by allowing the acid to react with acetylene. Because of the good availability, vinyl esters of saturated aliphatic monocarboxylic acids having 9 to 11 carbon atoms which are branched on the alpha carbon atom are particularly preferably used.
  • N, N-diethylamino-alpha-methylstyrene all isomers
  • N, N-die ylaminostyrene all isomers
  • allylamine crotylamine
  • Diarylethylenes in particular those of the general formula V:
  • radicals R 7 , R 8 , R 9 and R 10 each independently represent hydrogen atoms or substituted or unsubstituted alkyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl, arylalkyl or arylcycloalkyl radicals with the proviso that at least two of the variables R 1 , R 2 , R 3 and R 4 stand for substituted or unsubstituted aryl, arylalkyl or arylcycloalkyl radicals, in particular substituted or unsubstituted aryl radicals.
  • alkyl radicals examples include methyl, ethyl, propyl, isopropyl, n-butyl, iso-butyl, tert. -Butyl, amyl, hexyl or 2-ethylhexyl.
  • suitable cycloalkyl radicals are cyclobutyl, cyclopentyl or cyclohexyl.
  • suitable alkylcycloalkyl radicals are methylenecyclohexane,. Ethylene cyclohexane or propane-l, 3-diyl-cyclohexane.
  • Suitable cycloalkylalkyl radicals are 2-, 3- or 4-methyl-, ethyl-, propyl- or butylcyclohex-1-yl.
  • suitable aryl radicals are phenyl, naphthyl or biphenylyl, preferably phenyl and naphthyl and in particular phenyl.
  • suitable alkyl aryl radicals are benzyl or ethylene or propane-1,3-diyl-benzene.
  • suitable cycloalkylaryl radicals are 2-, 3- or 4-phenylcyclohex-l-yl.
  • Suitable arylalkyl radicals are 2-, 3- or 4-methyl-, ethyl-, propyl- or butylphen-1-yl.
  • suitable arylcycloalkyl radicals are 2-, 3- or 4-cyclohexylphen-l-yl.
  • the aryl radicals R 7 , R 8 , R 9 and / or R 10 are preferably phenyl or naphthy radicals, in particular phenyl radicals.
  • the substituents optionally present in the radicals R 7 , R 8 , R 9 and / or R 10 are electron-withdrawing or electron-donating atoms or organic radicals, in particular halogen atoms, nitrile, nitro, partially or fully halogenated alkyl, cycloalkyl, alkylcycloalkyl , Cycloalkylalkyl, aryl, alkylaryl, cycloalkylaryl, arylalkyl and arylcycloalkyl radicals; Aryloxy, alkyloxy and cycl ⁇ alkyloxy radicals; Arylthio, alkylthio and cycloalkylthio residues and / or primary, secondary and / or tertiary amino groups.
  • Diphenylethylene, dinaphthaleneethylene, ice or trans-stilbene, vinylidene-bis (4-N, N-dimemylaminobenzene), vinylidene-bis (4-aminobenzene) or vinylidene-bis (4-nitrobenzene), in particular diphenylethylene (DPE) are particularly advantageous ), which is why they are preferred.
  • the monomers (a35) are used in order to regulate the copolymerization advantageously in such a way that a free-radical copolymerization in batch mode is also possible.
  • Cyclic and / or ayclic olefins such as ethylene, propylene, but-1-ene, pent-1-ene, hex-1-ene, cyclohexene, cyclopentene, norbornene, butadiene, isoprene, cyclopentadiene and / or dicyclopentadiene.
  • Monido-containing monomers such as (meth) acrylic amides such as (mem) acrylic amide, N-methyl, N, N-dimethyl, N-ethyl, N, N-diethyl, N-propyl, N, N-dipropyl, N -Butyl-, N, N-dibutyl-, N-cyclohexyl-, N, N- cyclohexyl-methyl- and / or N-methylol-, N, N-dimethylol-, N-methoxymethyl-, N, N-Di ( methoxymethyl) -, N-ethoxymethyl- and / or N, N-di (ethoxyethyl) - (Meth) acrylamide; monomers containing carbamate groups such as
  • Monomers containing epoxy groups such as the glycidyl ester of acrylic acid, methacrylic acid, ethacrylic acid, crotonic acid, maleic acid, fumaric acid and / or itaconic acid.
  • Vinylaromatic hydrocarbons such as styrene, vinyltoluene, diphenylethylene or alpha-alkylstyrenes, especially alpha-methylstyrene;
  • Vinyl compounds especially vinyl and / or vinylidene dihalides such as
  • Vinyl chloride vinyl fluoride, vinylidene dichloride or vinylidene difluoride; N-Vmylamides such as vinyl-N-methylformamide, N-vinylcaprolactam or N-vinylpyrrolidone; 1-vinylimidazole; Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether and / or vinyl cyclohexyl ether; and / or vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl pivalate and / or the vinyl ester of 2-methyl-2-ethylheptanoic acid.
  • N-Vmylamides such as vinyl-N-methylformamide, N-vinylcaprolactam or N-vinylpyrrolidone
  • 1-vinylimidazole Vinyl ethers such as ethyl vinyl ether
  • Allyl compounds especially allyl ethers and esters such as allyl methyl, ethyl, propyl or butyl ether or allyl acetate, propionate or butyrate.
  • Monomers (a313: Polysiloxane macromonomers which have a number average molecular weight Mn of 1,000 to 40,000 and an average of 0.5 to 2.5 ethylenically unsaturated double bonds per molecule; in particular
  • Polysiloxane macromonomers that have a number average molecular weight Mn of. 2,000 to 20,000, particularly preferably 2,500 to 10,000 and in particular 3,000 to 7,000 and on average 0.5 to 2.5, preferably 0.5 to 1.5, ethylenically unsaturated double bonds per molecule, as described in DE 38 07 571 A. 1 on pages 5 to 7, DE 37 06 095 AI in columns 3 to 7, EP 0 358 153 B 1 on pages 3 to 6, in US 4,754,014 A 1 in columns 5 to 9, in the DE 4421 823 A1 or in international patent application WO 92/22615 on page 12, line 18, to page 18, line 10.
  • the monomers (al) and (a3) and optionally (a2) are selected so that the OH numbers and glass transition temperatures given above result.
  • the monomers (a3) which contain reactive functional groups are selected by type and amount so that they do not inhibit or completely inhibit the crosslinking reactions of the hydroxyl groups with the adducts (B) and / or crosslinking agents (C) described below in the second component prevent.
  • Tg glass transition temperature of the poly (meth) acrylate
  • W n weight fraction of the nth monomer
  • Tg n glass transition temperature of the homopolymer from the nth monomer
  • x number of different monomers.
  • the production of the (meth) acrylate copolymers (A) to be used according to the invention also has no special procedural features, but takes place with the aid of the methods known and known in the plastics field of continuous or discontinuous radical-initiated copolymerization in bulk, solution, emulsion, miniemulsion or microemulsion Normal pressure or overpressure in stirred tanks, autoclaves, tubular reactors, loop reactors or Taylor reactors at temperatures from 50 to 200 ° C.
  • Suitable free-radical initiators are dialkyl peroxides, such as di-tert-
  • Butyl peroxide or dicumyl peroxide Hydroperoxides, such as cumene hydroperoxide or tert-butyl hydroperoxide; Peresters, such as tert-butyl perbenzoate,
  • a monium peroxodisulfate for example azo dinitriles such as A-zobisisobutyronitrile; C-C-cleaving initiators such as benzpinacol silyl ether; or a combination of a non-oxidizing initiator with hydrogen peroxide. Combinations of the initiators described above can also be used.
  • Comparatively large amounts of free-radical initiator are preferably added, the proportion of the initiator in the reaction mixture, based in each case on the total amount of the monomers (a) and the initiator, particularly preferably 0.2 to 20% by weight, very particularly preferably 0.5 is up to 15% by weight and in particular 1.0 to 10% by weight.
  • thiocarbonylthio compounds or mercaptans such as dodecyl mercaptan can be used as chain transfer agents or molecular weight regulators.
  • the (meth) acrylate copolymers (A) are preferably selected according to the type and amount such that the coating materials adhesives, and - sealing compounds after curing has a storage modulus E 'in the rubber-elastic range of at least l ⁇ 7> °' p a un ⁇ _ ⁇ a Have a loss factor tan ⁇ at 20 ° C of a maximum of 0.10, the memory module E 'and the loss factor having been measured using dynamic mechanical thermal analysis on free films with a layer thickness of 40 + 10 ⁇ m (cf. the German patent DE 197 09467 C 2).
  • the content of the (meth) acrylate copolymer (A) described above in the coating materials, adhesives and sealing compounds according to the invention can vary widely.
  • the content depends in particular on the functionality of the binders on the one hand and the functionality of the adducts (B) and the crosslinking agents (D) described below on the other.
  • the content is preferably 5.0 to 80, preferably 6.0 to 75, particularly preferably 7.0 to 70, very particularly preferably 8.0 to 65 and in particular 9.0 to 60% by weight, in each case based on the Solids content of the coating materials, adhesives and sealants according to the invention.
  • the binder component to be used according to the invention can contain customary and known additives (C) in effective amounts. It is essential that they do not inhibit or completely prevent the crosslinking reactions.
  • suitable additives (C) are color and / or effect pigments, organic and inorganic, transparent or opaque fillers, nanoparticles, thermally and / or reactive diluents curable with actinic radiation, low-boiling organic solvents and high-boiling organic solvents ("long solvents") , Water, UV absorbers, light stabilizers, free radical scavengers, thermolabile free radical initiators, photoinitiators and co-initiators, other additional binders, crosslinking agents, such as are used in one-component systems, catalysts for thermal crosslinking, deaerating agents, slip additives, polymerization inhibitors, defoamers, emulsifiers, mesh and diperging agents, adhesion promoters, leveling agents, film-forming aids, sag control agents (SCA), rheology control additives (thickeners), flame retardants, siccatives, drying agents,
  • SCA sag control agents
  • Hautverhinde ⁇ mgsstoff corrosion inhibitors, waxes, matting agents, precursors of organically modified ceramic materials or additional binders.
  • the type and amount of additives (C) depend on the intended use of the coatings produced using the coating materials of the invention.
  • a coating material according to the invention is used to produce solid-color top coats or basecoats, it usually contains color and / or effect pigments (C) and, if appropriate, opaque fillers. If a coating material according to the invention is used, for example, to produce clearcoats or sealers - which is the preferred use - these additives (C) are naturally not present in the coating material in question.
  • Suitable effect pigments (C) are platelet pigments such as commercially available aluminum bronzes, aluminum bronze chromated according to DE 36 36 183 A1, and commercially available stainless steel bronzes and non-metallic effect pigments, such as pearlescent or interference pigments.
  • platelet pigments such as commercially available aluminum bronzes, aluminum bronze chromated according to DE 36 36 183 A1
  • non-metallic effect pigments such as pearlescent or interference pigments.
  • suitable inorganic color pigments (C) are titanium dioxide, iron oxides, Sicotrans yellow and carbon black.
  • suitable organic color pigments (C) are thioindigo pigments indanthrene blue, cromophthal red, irgazine orange and heliogen green.
  • Römpp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, 1998 pages 180 and 181, "iron blue pigments” to "iron oxide black”, pages 451 to 453 “pigments” to “pigment volume concentration”, page 563 "thioindigo pigments” and See page 567 “Titanium dioxide pigments”.
  • organic and inorganic fillers are chalk, calcium sulfates, barium sulfate, silicates such as talc or kaolin, silicas, oxides such as aluminum hydroxide or magnesium hydroxide or organic fillers such as textile fibers, cellulose fibers, polyethylene fibers or wood flour.
  • silicates such as talc or kaolin
  • silicas oxides such as aluminum hydroxide or magnesium hydroxide
  • organic fillers such as textile fibers, cellulose fibers, polyethylene fibers or wood flour.
  • thermally curable reactive diluents are positionally isomeric diethyloctanediols or hydroxyl group-containing hyperbranched compounds or dendrimers, as are described, for example, in the unpublished German patent application DE 198 50 243.
  • Suitable reactive thinners (C) curable with actinic radiation are those described in Römpp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, Stuttgart, New York, 1998, on page 491 under the keyword “reactive thinners”.
  • Suitable low-boiling organic solvents (C) and high-boiling organic solvents (C) ("long solvents") are ketones such as methyl ethyl ketone or methylHsobutyl ketone, esters such as ethyl acetate or butyl acetate, ethers such as dibutyl ether or ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol Butylene glycol or
  • thermolabile radical initiators (C) are organic peroxides, organic azo compounds or CC-cleaving initiators such as dialkyl peroxides, peroxocarboxylic acids, peroxodicarbonates, peroxide esters, hydroperoxides, ketone peroxides, azodinitriles or benzpinacol silyl ethers.
  • suitable catalysts (C) for crosslinking are dibutyltin dilaurate, lithium decanoate or zinc octoate.
  • Suitable other additional binders (C) are oligomeric and polymeric, linear and / or thermally and / or curable with actinic radiation
  • alkyds alkyds, acrylated polyesters, polylactones, polycarbonates, polyethers, epoxy resin-amine adducts, (meth) acrylate diols, partially saponified polyvinyl esters, polyurethanes and acrylated polyurethanes, such as those in the patents EP 0521 928 A 1, EP 0 522420 A1, EP 0522419 A1, EP 0 730 613 A1 or DE 44 37 535 A1, or polyureas.
  • Suitable additional crosslinking agents (C) are aminoplast resins, as described, for example, in Römpp Lexikon Lacke und Druckmaschine, Georg Thieme Verlag, 1998, page 29, “Aminoharze”, the textbook “Lackadditive” by Johan Bieleman, Wiley-VCH, Weinheim, New York , 1998, pages 242 ff., The book
  • Suitable deaerating agents (C) are diazadicycloundecane or benzoin.
  • emulsifiers (C) are nonionic emulsifiers, such as alkoxylated alkanols and polyols, phenols and alkylphenols or anionic emulsifiers such as alkali metal salts or ammonium salts of alkane carboxylic acids, alkane sulfonic acids, and sulfonic acids of alkoxylated alkanols and polyols, phenols and alkylphenols.
  • nonionic emulsifiers such as alkoxylated alkanols and polyols, phenols and alkylphenols
  • anionic emulsifiers such as alkali metal salts or ammonium salts of alkane carboxylic acids, alkane sulfonic acids, and sulfonic acids of alkoxylated alkanols and polyols, phenols and alkylphenols.
  • Suitable wetting agents (C) are siloxanes, fluorine-containing compounds, carboxylic acid half-esters, phosphoric acid esters, polyacrylic acids and their copolymers or polyurethanes.
  • a suitable adhesion promoter is tricyclodecanedimethanol.
  • suitable film-forming aids are cellulose derivatives such as cellulose acetobutyrate (GAB).
  • Suitable transparent fillers (C) are those based on silicon dioxide, aluminum oxide or zirconium oxide; In addition, reference is made to the Römpp Lexicon Lacke und Druckmaschine, Georg Thieme Verlag, Stuttgart, 1998, pages 250 to 252.
  • Sag control agents are ureas, modified ureas and / or silicas, as described, for example, in references EP 0 192 304 A1, DE 23 59 923 A1, DE 18 05 693 A1, WO 94/22968, DE 27 51 761 C 1, WO 97/12945 or "färbe + lack", 11/1992, pages 829 ff.
  • rheology-controlling additives are those known from the patents WO 94/22968, EP 0 276 501 A1, EP 0 249 201 A1 or WO 97/12945; crosslinked polymeric microparticles, as disclosed, for example, in EP 0 008 127 A1; inorganic layered silicates such as aluminum-magnesium-silicates, sodium-magnesium and sodium-magnesium-fluorine-lithium layered silicates of the montmorillonite type; Silicas such as aerosils; or synthetic polymers with ionic and / or associative groups such as polyvinyl alcohol, poly (meth) acrylamide, poly (meth) acrylic acid, polyvinyl pyrrolidone, styrene-maleic anhydride or emylene-maleic acid hydride copolymers and their derivatives or hydrophobically modified ethoxylated urethanes or polyacrylates;
  • An example of a suitable matting agent (C) is magnesium stearate.
  • Suitable precursors (C) for organically modified ceramic materials are hydrolyzable organometallic compounds, in particular of silicon and aluminum. Further examples of the additives (C) listed above and examples of suitable UV absorbers, radical scavengers, leveling agents,
  • the preparation of the binder component to be used according to the invention has no special features, but is carried out in a customary and known manner by mixing the constituents (A) and optionally (C) described above in suitable mixing units such as stirred kettles, dissolvers, agitator mills or extruders.
  • the second component of the coating materials, adhesives and sealants according to the invention contains at least one adduct (B).
  • the adduct (B) can be prepared from a diisocyanate (bl) and a compound I (b2).
  • the compounds I have an isocyanate-reactive functional group.
  • suitable isocyanate-reactive functional groups are
  • R 1 and R 2 independently of one another represent hydrogen atoms or alkyl radicals having 1 to 10 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl , Isoamyl, n-hexyl, n-heptyl, n-octyl, 2-ethyl-hex-1-yl, n-nonyl or n-decyl, especially isopropyl;
  • X and Y independently of one another represent oxygen atoms, sulfur atoms or residues> NR 6 , in which R 6 is an aliphatic residue with 1 to 30 carbon atoms, the carbon chain of which may be interrupted by one or more oxygen atoms, such as the residues R 1 and R 2 described above , Undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosanyl or ohgo (ethylene glycol) -l-yl, oligo (propylene glycol) -l-yl or oligo (butylene glycol) -l-yl or the corresponding mixed oligomers with a degree of oligomerization of up to 15.
  • R 6 can be an aromatic radical having 6 to 30 carbon atoms, such as phenyl, naph
  • R 3 stands for an alkylene radical with 1 to 5 carbon atoms such as methylene, eth-1,2-ylene, trimethylene, tetramethylene or pentamethylene.
  • R 4 and R 5 independently of one another represent hydrogen atoms, isocyanate-reactive functional groups or radicals R 6 .
  • a radical R 4 , R 5 or R 6 contains an isocyanate-reactive functional group or a radical R 4 or R 5 is an isocyanate-reactive functional group, the other radicals R 4 , R 5 or R 6 - if present - have no isocyanate-reactive _functional groups.
  • radicals R 1 , R 2 , R 4 , R 5 and R 6 have the meaning given above, the radicals R 4 or R 6 containing an isocyanate-reactive functional group.
  • oxazolidines have particular advantages, which is why they are used with particular preference according to the invention.
  • particularly suitable oxazolidines (IN) are ⁇ - (2-hydroxyethyl) -1, 3-oxazolidine or N- (2-hydroxyethyl) -2-isopropyl-1,3-oxazolidine, as described on page 6, table 1, No. 5a and No. 5b, the German patent application DE 196 09 617 A1 are described.
  • the molar ratio of isocyanate groups in the dusocyanates (b1) to the isocyanate-reactive functional groups in the compound I (b2) is 0.8: 1.2 to 1.2: 0, 8, preferably 0.9: 1.1 to 1.1: 0.9 and in particular 1: 1.
  • the content of the adducts (B) described above in the coating materials, adhesives and sealants according to the invention can vary very widely. It depends in particular on the functionality of the crosslinking agents (D) and the (meth) acrylate copolymers (A) and on the viscosity of the coating materials, adhesives and sealants according to the invention.
  • the content is preferably 20 to 90, preferably 22 to 85, particularly preferably 23 to 80, very particularly preferably 24 to 75 and in particular 25 to 70% by weight, in each case based on the solids content of the coating materials, adhesives and sealants according to the invention, where the content of (B) up to twice as high as the content of (A) can be chosen.
  • the second component to be used according to the invention may also contain at least one reactive crosslinking agent (D).
  • this crosslinking agent (D) can also be present in a third component to be used according to the invention.
  • a reactive crosslinking agent (D) is understood to mean a crosslinking agent which, in contrast to the crosslinking agents (C) described above, for one-component systems is already below 90, preferably below 70, preferably below 60, particularly preferably below 50, particularly preferably below 40, very particularly preferably below 30 ° C and in particular at room temperature with those described above
  • Method acrylate copolymers (A), the adducts (B) after cleavage as well as react with any available reactive diluents (C) for thermal curing.
  • Suitable reactive crosslinking agents (D) are polyisocyanates which, on a statistical average, have more than two isocyanate groups in the molecule and are, if appropriate, modified hydrophilically or hydrophobically.
  • the polyisocyanates (D) are preferably liquid and preferably of low viscosity, so that they can easily be incorporated into the second component or into the mixture of the first and second components.
  • Polyisocyanates (D) with 2 to 5 isocyanate groups per molecule and with viscosities at 23 ° C. of 100 to 2000 mPa.s are particularly preferably used.
  • organic solvents (C), preferably 1 to 25% by weight, based on pure polyisocyanate (D), can also be added to the polyisocyanates (D), in order to improve the incorporation of the polyisocyanate (D). to improve and, if necessary, to lower its viscosity to a value within the above-mentioned ranges.
  • polyisocyanates (D) are polyurethane prepolymers containing isocyanate groups, which can be prepared by reacting polyols with an excess of the above-described diisocyanates (b1) and are preferably low-viscosity.
  • Polyisocyanates (D) containing isocyanurate, biuret, allophanate, iminooxadiazinedione, urethane, urea and / or uretdione groups can also be used.
  • Polyisocyanates containing urethane groups are obtained, for example, by reacting some of the isocyanate groups with polyols, such as, for example, trimethylolpropane and glycerol.
  • Aliphatic or cycloaliphatic diisocyanates (b1) in particular hexamethylene diisocyanate, dimerized and trimerized hexamethylene diisocyanate, isophorone diisocyanate, 2-isocyanatopropylcyclohexyl isocyanate, dicyclohexylmethane-2,4'-diisocyanate or dicyclohexyl methane-4,4'-diisocyanate or mixtures of these diisocyanate or 4,4'-diisocyanate, are preferably used.
  • the content of the crosslinking agents (D) described above in the coating materials, adhesives and sealants according to the invention can also vary very widely. In particular, it depends on the functionality of the crosslinking agent (D) and the (meth) acrylate copolymer (A) and the amount of adduct (B).
  • the content is preferably 20 to 70, preferably 22 to 65, particularly preferably 23 to 60, very particularly preferably 24 to 55 and in particular 25 to 50% by weight, in each case based on the solids content of the coating materials, adhesives and sealants according to the invention.
  • the second component to be used according to the invention or - if used - also or only the third component to be used according to the invention may contain at least one of the additives (C) described above, provided that these are not combined with the adducts (B) and / or the crosslinking agents (D ) enter undesirable reactions such as decomposition reactions or premature crosslinking reactions.
  • additives (C) described above which are used in the coating materials, adhesives and sealants according to the invention, may also be present as a separate, separate, third or fourth component.
  • the production of the coating materials, adhesives and sealants according to the invention from the components described above does not offer any special features in terms of method, but rather is carried out with the aid of the customary and known Mixing devices and methods described above or by means of conventional two- or multi-component metering and mixing were carried out. Ideally, the mixing is done by hand.
  • the coating materials, adhesives and sealants according to the invention are used to produce coatings, adhesive layers and seals on and / or in primed and unprimed substrates.
  • the coating materials according to the invention are used to produce solid-color top coats, clear coats and base coats and clear coats in multi-coat paint and / or effect coatings.
  • the application of the coating materials according to the invention has no peculiarities, but can be done by all customary application methods, such as Spraying, knife coating, brushing, pouring, dipping, trickling or rolling.
  • Spraying knife coating, brushing, pouring, dipping, trickling or rolling.
  • Spray application methods are used, such as compressed air spraying, airless spraying, high rotation, electrostatic spray application (ESTA), if appropriate combined with hot spray application such as hot air - hot spraying.
  • compressed air spraying airless spraying
  • high rotation high rotation
  • electrostatic spray application ESTA
  • hot spray application such as hot air - hot spraying.
  • Suitable substrates are surfaces which are not damaged by hardening of the coating materials, adhesives and / or sealing compounds located thereon using heat and, if appropriate, actinic radiation; these are e.g. B. metals, plastics, wood, ceramics, stone, textiles, fiber composites, leather, glass, glass fibers, glass and stew wool, mineral and resin-bound building materials, such as gypsum and cement boards or roof tiles, as well as composites of these materials.
  • the coating materials, adhesives and sealants according to the invention are also suitable for applications outside the automotive industry. Here they come in particular for painting, gluing and or sealing furniture, windows, doors, buildings indoors and outdoors and the industrial painting, including coil coating, container coating and the impregnation or coating of electrical components.
  • primers can be used which are produced in a customary and known manner from electrocoat materials (ETL), and both anodic (ATL) and cathodic (KTL) electrocoat materials, but especially KTL, are suitable.
  • ETL electrocoat materials
  • ATL anodic
  • KTL cathodic
  • the electrocoating or electrocoating layer can be coated with a filler which is cured either on its own or together with the electrocoating layer (wet-on-wet method).
  • the overlay with a filler takes place in particular in areas that are exposed to strong mechanical stress, such as stone chips.
  • suitable fillers in particular aqueous fillers, which are also referred to as stone chip protection primers or functional layers, are made of US Pat. Nos. 4,537,926 A1, EP 0 529 335 A1, EP 0 595 186 A1, EP 0 639 660 A1, DE 44 38 504 A1, DE 43 37 961 A1, WO 89/10387 , US 4,450,200 A1, US 4,614,683 A1 or WO 94/26827.
  • Primed or unprimed plastic parts made of e.g. B. ABS, AMMA, ASA, CA, GAB, EP, UF, CF, MF, MPF, PF, PAN, PA, PE, HDPE, LDPE, LLDPE, UHMWPE, PC, PC / PBT, PC / PA, PET, PMMA, PP, PS, SB, PUR, PVC, RF, SAN, PBT, PPE, POM, PUR-RIM, SMC, BMC, PP-EPDM and UP (short names according to DIN 7728T1) can be painted, glued or sealed. In the case of non-functionalized and / or non-polar substrate surfaces, these can be subjected to a pretreatment, such as with a plasma or with flame treatment, or provided with a hydro primer in a known manner before the coating.
  • a pretreatment such as with a plasma or with flame treatment, or provided with a hydro primer in a known manner before the coating.
  • the coating materials of the suitable composition according to the invention are applied to the substrates described above to produce the clearcoats and solid-color lacquers according to the invention, after which the resulting clearcoat and solid-color lacquer layers are cured.
  • the adhesives and sealants according to the invention are applied to and / or in the substrates described above.
  • the surfaces to be bonded of two or more substrates are preferably coated with the adhesive according to the invention, after which the surfaces in question may be brought into contact under pressure and the resulting adhesive layers are cured.
  • a multi-layer paint and / or effect paint system according to the invention is produced on a primed or unprimed substrate (1) applying a basecoat to the substrate,
  • a basecoat known per se and a clearcoat according to the invention are used as the clearcoat.
  • a clear lacquer known per se and a basecoat according to the invention are used as the basecoat.
  • a basecoat 20 according to the invention and a clearcoat according to the invention are used.
  • Clearcoats known per se are one- or multi-component clearcoats, powder clearcoats, powder slurry clearcoats, UV-curable clearcoats or sealers, as described in patent applications, patent specifications and publications DE 4204 518 A1, EP 0 594 068 A1, EP 0 594071 A1, EP 0 594 142 A 1, EP 0 604 992 A 1, EP 0 596460 A 1, WO 94/10211, WO 94/10212, WO 94/10213, WO 94/22969 or WO 92/22615, US 5,474,811 A 1, US 5,356,669 A 1 or US 5,605,965 A 1, DE 42 22 194 A 1, product information from BASF Lacke + Maschinen AG, "Powder Coatings", 1990, company lettering from BASF Coatings AG "Powder Coatings, Powder Coatings for Industrial Applications", January 2000, US 4,268,542 A1, DE
  • EP 0 650 978 A1 , EP 0 650 979 A1, EP 0 650
  • the hardening of the applied coating materials, adhesive layers and sealing compounds according to the invention has no special features in terms of method, but rather generally takes place at room temperature in the course of 30 minutes to several days, for example 4 to 10 days. Hardening can be supported by the application of heat and / or actinic radiation. This is particularly the case if the coating materials, adhesive layers and sealing compounds according to the invention contain constituents (C) Contain, which can be activated with actinic radiation, and / or constituents (C), which are curable from other countries, such as the crosslinking agent (C) for one-component systems.
  • actinic radiation is understood to mean electromagnetic radiation such as near infrared, visible light, UV light or X-rays, but especially UV light, and corpuscular radiation, in particular electron radiation.
  • the appropriate radiation sources, such as UV lamps, are used for curing.
  • the coating materials, adhesives and sealants according to the invention have a high solids content with low viscosity and a long service life.
  • the resulting coatings according to the invention in particular the solid-color topcoats, clearcoats and color and or effect-giving multi-layer coatings, have high hardness, flexibility and chemical resistance, an excellent flow, a very good interlayer adhesion, an excellent overall optical impression, a very good weather resistance, a very high Scratch resistance and very good polishability.
  • the adhesive layers according to the invention are permanently strong, even under extreme and / or very strongly and rapidly changing climatic conditions.
  • the seals according to the invention completely seal off chemically aggressive substances.
  • primed and unprimed substrates according to the invention which are coated with at least one coating according to the invention, bonded with at least one adhesive layer according to the invention and / or sealed with at least one seal according to the invention, have a particularly long service life in addition to the advantages listed above, which they economically particularly valuable.
  • the resulting methacrylate copolymer (A) to be used according to the invention had a (theoretical) hydroxyl number of 175 mg KOH / g, a number average molecular weight Mn of 3,973, a weight average molecular weight Mw of 13,600 and a non-uniformity Mw / Mn of 3.42.
  • N- (2-hydroxyethyl) -2-isopropyl-1,3-oxazolidine was, as described on page 9, lines 7 to 17, line 6, "V4 - Monourethane from HDI", which is described in DE 196 09 617 A1 HDI in a molar ratio of 1: 1 to the adduct (B) implemented.
  • the clearcoats of Examples 1 and 2 were coated on test panels which had an electro-dip coating with a layer thickness of 18-22 ⁇ m, a filler with a layer thickness of 35-40 ⁇ m and a black basecoat with a layer thickness of 12-15 ⁇ m applied in a layer thickness of 40 - 45 ⁇ m and cross-linked at 80 ° C.
  • the paint surface was damaged with a sieve fabric that was loaded with a mass.
  • the screen fabric and the varnish surface were wetted liberally with a detergent solution.
  • the test board was pushed back and forth in a lifting motion under the screen by means of a motor drive.
  • test specimen was eraser covered with nylon sieve mesh (No. 11, 31 ⁇ m mesh size, Tg 50 ° C.) (4.5 ⁇ 2.0 cm, wide side perpendicular to the direction of scratching).
  • the coating weight was 2000 g.
  • non-baked test panels were baked at 100 ° C for 20 minutes to determine the Fischerscope-Emdring hardness and another part of the non-baked test panels were baked at 140 ° C for 20 minutes. The results can also be found in the table.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne des substances de revêtement, substances adhésives et masses d'étanchéité à plusieurs constituants, comprenant : (A) un copolymère (méth)acrylate qui contient jusqu'à 90 % en poids vis-à-vis de (A), de monomères incorporés par polymérisation, à base de groupes hydroxyle, (a1) représentant 20 à 90 % en poids vis-à-vis de (A) de 4-hydroxybutyl(méth)acrylate et/ou 2-alkyl-propane-1,3-diol-mono(méth)acrylate, et (a2) représentant 0 à 40 % en poids vis-à-vis de (A) d'autres monomères à base de groupes hydroxyle ; et (B) un produit d'addition pouvant être préparé à partir de (b1) un diisocyanate et (b2) un composé de formule générale (I) comprenant un groupe réactif à l'isocyanate. Dans ladite formule (I) : R<1> et R<2> représentent des atomes d'hydrogène ou des groupes alkyle ; X et Y représentent des atomes d'oxygène, des atomes de soufre ou >N-R<6> où R<6> est un groupe alkyle ou aryle ; R<3> représente un groupe alkylène ; et R<4> et R<5> des atomes d'hydrogène, des groupes réactifs à l'isocyanate ou des groupes R<6>, où R<4>, R<5> ou R<6> contiennent un groupe réactif à l'isocyanate, ou R<4> ou R<5> est un groupe fonctionnel réactif à l'isocyanate, où R<4>, R<5> ou R<6> - s'ils sont présents ne présentent pas de groupe réactif à l'isocyanate, et le rapport molaire des groupes isocyanate contenus dans (b1) par rapport aux groupes réactifs à l'isocyanate contenus dans le composé de formule (I), vaut environ 1,0.
EP01933891A 2000-04-29 2001-04-26 Substances de revetement, substances adhesives et masses d'etancheite a plusieurs constituants, ainsi que leur utilisation Withdrawn EP1278791A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10021139A DE10021139B4 (de) 2000-04-29 2000-04-29 Mehrkomponentenbeschichtungsstoffe, -klebstoffe und -dichtungsmassen und ihre Verwendung
DE10021139 2000-04-29
PCT/EP2001/004700 WO2001083579A1 (fr) 2000-04-29 2001-04-26 Substances de revetement, substances adhesives et masses d'etancheite a plusieurs constituants, ainsi que leur utilisation

Publications (1)

Publication Number Publication Date
EP1278791A1 true EP1278791A1 (fr) 2003-01-29

Family

ID=7640391

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01933891A Withdrawn EP1278791A1 (fr) 2000-04-29 2001-04-26 Substances de revetement, substances adhesives et masses d'etancheite a plusieurs constituants, ainsi que leur utilisation

Country Status (5)

Country Link
US (1) US6756072B2 (fr)
EP (1) EP1278791A1 (fr)
AU (1) AU2001260252A1 (fr)
DE (1) DE10021139B4 (fr)
WO (1) WO2001083579A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10047989A1 (de) * 2000-09-28 2002-04-18 Basf Coatings Ag Thermisch und mit aktinischer Strahlung härtbare Mehrkomponentenbeschichtungsstoffe, -klebstoffe und -dichtungsmassen und ihre Verwendung
DE10140155A1 (de) * 2001-08-16 2003-03-06 Basf Coatings Ag Thermisch sowie thermisch und mit aktinischer Strahlung härtbare Beschichtungsstoffe und ihre Verwendung
DE10140145A1 (de) * 2001-08-16 2003-03-06 Basf Coatings Ag Thermisch und mit aktinischer Strahlung härtbare Beschichtungsstoffe und ihre Verwendung
DE10153645A1 (de) * 2001-10-31 2003-05-22 Basf Coatings Ag Härtbares Stoffgemisch, Verfahren zu seiner Herstellung und seine Verwendung
DE10241299A1 (de) 2002-09-04 2004-03-25 Basf Ag Strahlungshärtbare Polyurethane mit verkappten Aminogrupppen
US6984693B2 (en) 2003-08-01 2006-01-10 E. I. Du Pont De Nemours And Company Two stage cure two component coating composition containing hydroxylbutyl acrylate polymers
US20060094944A1 (en) 2004-10-28 2006-05-04 Sontra Medical Corporation System and method for analyte sampling and analysis with error correction
BRPI0813675A8 (pt) * 2007-06-20 2018-08-28 Basf Se método para aplicar um revestimento de proteção contra corrosão em uma superfície metálica, e, preparação para aplicar um revestimento de proteção contra corrosão em uma superfície metálica
US8686060B2 (en) 2009-08-03 2014-04-01 Morgan Adhesives Company Adhesive compositions for easy application and improved durability
US8242185B2 (en) * 2009-08-03 2012-08-14 Morgan Adhesives Company Adhesive compositions for easy application and improved durability
KR101716543B1 (ko) * 2014-04-30 2017-03-15 제일모직주식회사 점착필름 및 이를 포함하는 광학표시장치
ES2747299T3 (es) 2016-04-27 2020-03-10 Sika Tech Ag Una composición de múltiples componentes para producir un hidrogel inhibidor de la corrosión
KR102144950B1 (ko) * 2017-09-29 2020-08-14 주식회사 엘지화학 점착 조성물 및 점착 필름

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US641646A (en) * 1899-04-27 1900-01-16 Mark K Edgar Instrument for removing dents from gun-barrels.
DE2446438C2 (de) * 1974-09-28 1985-04-11 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Oxazolidingruppen enthaltenden Urethanen und ihre Verwendung
DE3234045A1 (de) * 1981-09-17 1983-03-24 Daicel Chemical Industries, Ltd., Sakai, Osaka 2-methylpropylenglycol-monoacrylat oder -diacrylat und das diacrylat enthaltende lichtempfindliche zusammensetzung
DE3201224A1 (de) * 1982-01-16 1983-07-28 Chemische Werke Hüls AG, 4370 Marl Lichtstabile pur-beschichtungen
DE4310414A1 (de) * 1993-03-31 1994-10-06 Basf Lacke & Farben Verfahren zur Herstellung einer zweischichtigen Decklackierung auf einer Substratoberfläche
DE4327853A1 (de) * 1993-08-19 1995-02-23 Bayer Ag Verfahren zur Herstellung von Überzügen
DE19609617A1 (de) * 1996-03-12 1997-09-18 Basf Ag Einkomponenten- und Zweikomponenten-Polyurethanbeschichtungsmassen
EP0752433B1 (fr) * 1995-07-01 2001-05-30 BASF Aktiengesellschaft Compositions de revêtement à base de polyuréthane à un ou deux composants
DE19524046A1 (de) * 1995-07-01 1997-01-02 Basf Ag Zweikomponenten-Polyurethanbeschichtungsmasse
DE19709465C2 (de) * 1997-03-07 2001-07-12 Basf Coatings Ag Beschichtungsmittel, Verfahren zur Herstellung von Mehrschichtlackierungen und Verwendung der Beschichtungsmittel hierfür
DE19709467C1 (de) * 1997-03-07 1998-10-15 Basf Coatings Ag Beschichtungsmittel sowie Verfahren zur Herstellung von Mehrschichtlackierungen
DE19731540A1 (de) * 1997-07-23 1999-01-28 Herberts Gmbh Überzugsmittel und deren Verwendung bei Verfahren zur Mehrschichtlackierung
DE19850243A1 (de) * 1998-10-31 2000-05-11 Basf Coatings Ag Flüssige Stoffgemische und (Co)Polymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von reaktiven Mehrstoffmischungen
DE19850210A1 (de) * 1998-10-31 2000-05-04 Basf Coatings Ag Die Verwendung von Methylpropan-1,3-diol-mono(meth)acrylat für die Herstellung oxidativ und/oder thermisch härtbarer Beschichtungsmittel, Klebstoffe und Dichtungsmassen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0183579A1 *

Also Published As

Publication number Publication date
DE10021139B4 (de) 2005-06-30
DE10021139A1 (de) 2001-11-15
WO2001083579A1 (fr) 2001-11-08
US6756072B2 (en) 2004-06-29
US20030104132A1 (en) 2003-06-05
AU2001260252A1 (en) 2001-11-12

Similar Documents

Publication Publication Date Title
EP1423449B1 (fr) Matieres de revetement durcissables thermiquement et par rayonnement actinique et leur utilisation
DE10039262B4 (de) Polyurethane, Verfahren zu deren Herstellung, sowie ihre Verwendung zur Herstellung von Pfropfmischpolymerisaten, Beschichtungsstoffen, Klebstoffen und Dichtungsmassen
EP1373422A1 (fr) Dispersions aqueuses durcissables par voie thermique et par rayonnement actinique, procede permettant les produire et leur utilisation
DE19948004A1 (de) Polyurethane und Pfropfmischpolymerisate auf Polyurethanbasis sowie ihre Verwendung zur Herstellung von Beschichtungsstoffen, Klebstoffen und Dichtungsmassen
DE10048849A1 (de) Verfahren zur Herstellung eines thermisch und mit aktinischer Strahlung härtbaren Mehrkomponentensystems und seine Verwendung
EP1425326A1 (fr) Polyurethanes et copolymeres greffes a base de polyurethane, et leur utilisation pour preparer des matieres de revetement, des matieres adhesives et des matieres d&#39;etancheite
EP1419015A2 (fr) Procede de production de revetements au moyen de substances de revetement pouvant etre durcies thermiquement et par rayonnement actinique
DE10048847A1 (de) Lösemittelhaltiges, thermisch und mit aktinischer Strahlung härtbares Mehrkomponentensystem und seine Verwendung
DE10021139B4 (de) Mehrkomponentenbeschichtungsstoffe, -klebstoffe und -dichtungsmassen und ihre Verwendung
DE10048275C1 (de) Thermisch und mit aktinischer Strahlung härtbares Mehrkomponentensystem und seine Verwendung
DE10048670A1 (de) Beschichtungsstoffsystem für die Herstellung farb- und/oder effektgebender Mehrschichtlackierungen auf der Basis von Mehrkomponentenbeschichtungsstoffen
DE19932497A1 (de) Wäßriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung
WO2002079308A1 (fr) Dispersions aqueuses libres ou essentiellement libres de composes organiques volatils, procede de fabrication et utilisation
EP1311579B1 (fr) Procede de preparation des matieres de revetement, des matieres adhesives et des matieres d&#39;etancheite
WO2002026852A1 (fr) Materiaux de revetement, adhesifs et produits d&#34;etancheite multicomposants durcissables thermiquement et par rayonnement actinique, et leur utilisation
EP1311580B1 (fr) Systemes a composante unique durcissable par reaction thermique et par rayonnement actinique et leur utilisation
WO2001085820A1 (fr) Substances d&#39;enduction, adhesifs et matieres d&#39;etancheite a plusieurs composants, et leur utilisation
EP1131362A1 (fr) Utilisation de methylpropane-1,3-diol-mono(meth)acrylate pour la production d&#39;agents de revetement, de colles et de materiaux d&#39;etancheite durcissables par voie oxydative et/ou thermique
DE10010416A1 (de) Pysikalisch oder thermisch und/oder mit aktinischer Strahlung härtbarer Beschichtungsstoff und seine Verwendung
EP1628782A1 (fr) Substances de revetement a une composante thermodurcissables, procede pour le preparer et leur utilisation
DE10020969A1 (de) Mehrkomponentenbeschichtungsstoffe, -klebstoffe und -dichtungsmassen und ihre Verwendung

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20020902

AK Designated contracting states

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17Q First examination report despatched

Effective date: 20050207

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20050818