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
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
• • 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
  • C08G18/67—Unsaturated compounds having active hydrogen
  • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
  • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
  • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
  • C08F220/04—Acids; Metal salts or ammonium salts thereof
  • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• • 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
  • C08G18/40—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
  • C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
  • C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/81—Unsaturated isocyanates or isothiocyanates
  • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
  • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
• • 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
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/31504—Composite [nonstructural laminate]
  • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

• the present invention relates to modified polyisocyanate mixtures based on polyisocyanates and polyacrylate units, to a process for preparing them and to their use as a curing component in polyurethane coating compositions.
• polyurethane coating compositions particularly if they are to be used in the vehicle, industrial or furniture sectors, especially great value is generally placed on the resistance of such coating compositions to different environmental influences.
• the criteria are frequently hardness, chemical resistance and solvent resistance, scratch resistance, including what is called “reflow”, light stability and weather resistance.
• U.S. Pat. No. 4,454,317 describes polyisocyanate containing isocyanurate groups which are obtainable by trimerizing HDI. Described by way of example is an HDI trimer having an NCO content of 20.8% by weight and a viscosity of 14 Pas at room temperature. This patent does not disclose anything regarding the possibility of using polyisocyanates of such high viscosity, in combination with suitable polyols, to prepare polyurethane coating compositions having improved chemical resistance.
• the modified polyisocyanate mixtures disclosed in DE-A 100 13 187 are notable for a high isocyanate functionality, but this is largely obtained at the expense of the isocyanate content of the respective polyisocyanate.
• high functionality or high molecular weight polyisocyanates by the oligomerization of diisocyanates by known isocyanate reactions such as biuretization, urethanization, trimerization and allophanatization, large numbers of isocyanate groups are generally consumed for these molecular weight-increasing and functionality-building isocyanate reactions.
• polyacrylate-modified polyisocyanate of the present invention which exhibit the required properties.
• These new polyisocyanates may be obtained by partial reaction of known polyisocyanates with hydroxy-functional unsaturated compounds to form urethane groups and subsequent polymerization of the unsaturated groups and optionally copolymerization with other unsaturated compounds.
• These new polyisocyanate mixtures are capable of broad variation in terms of their composition, their molecular weight and their functionality and thus in terms of their overall profile of properties.
• the modified polyisocyanate mixtures of the invention have very good compatibility with a multitude of polyols and can be formulated to polyurethane coating compositions having a broad spectrum of properties. Particularly advantageous when compared to the corresponding base polyisocyanates have proven to be the markedly improved physical drying and significantly higher solvent resistance and chemical resistance of corresponding polyurethane coating compositions, particularly those based on HDI, without loss of toughness and elasticity, the good reflow or the high scratch resistance.
• the present invention relates to polyacrylate-modified polyisocyanates which are i) prepared from aromatic, araliphatic, cycloaliphatic and/or aliphatic polyisocyanates having an NCO content of 5% to 25% by weight, an NCO functionality ⁇ 2, a viscosity measured as solvent free resin of 150 to 200,000 mPa ⁇ s at 23° C., and ii) contain at least one structural unit of the formula (I)
• R 1 is an optionally heteroatom-containing hydrocarbon radical
• R 2 is a hydrocarbon radical having at least one isocyanate group and optionally urethane, allophanate, biuret, uretdione, isocyanurate and/or iminooxadiazinedione groups and
• n is a number ⁇ 1.
• the present invention also relates to a process for preparing these polyisocyanates by reacting a portion of the isocyanate groups of
• the present invention also relates to binder compositions containing the polyacrylate-modified polyisocyanates of the invention, optionally having blocked NCO groups, and a compound having NCO-reactive groups.
• the present invention also relates to water-dilutable or aqueous binder compositions containing the polyacrylate-modified polyisocyanates of the invention, wherein a portion of the NCO groups have been hydrophilically modified with polyether units, and a compound having NCO-reactive groups.
• the hydrocarbon radical R 2 is based preferably on aromatic, cycloaliphatic, araliphatic and/or aliphatic di- and/or polyisocyanates and preferably contains at least one of the structural units referred to as optional.
• Starting polyisocyanates A) include the di- and/or polyisocyanates which are known in polyurethane chemistry. It is immaterial whether these isocyanates are prepared with phosgene or by phosgene-free processes.
• Preferred starting polyisocyanates are lacquer polyisocyanates containing urethane, uretdione, allophanate, biuret, isocyanurate and/or iminooxadiazinedione groups and prepared from monomeric di- or triisocyanates.
• Monomeric isocyanates which can be used alone or in admixture include 1,6-di-isocyanatohexane, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate), 4,4′-diisocyanatodicyclohexylmethane, 4-isocyanatomethyl-1,8-octane diisocyanate, 1,4-diisocyanatocyclohexane, 1-methyl-2,4-diisocyanatocyclohexane and mixtures thereof with up to 35% by weight, based on the total mixture, of 1-methyl-2,6-diisocyanatocyclohexane, and 2,4-diisocyanatotoluene (TDI) and its mixtures with up to 35% by weight, based on the total mixture, of 2,6-diisocyanatototoluene.
• TDI
• lacquer polyisocyanates are used as component A). They include lacquer polyisocyanates containing urethane groups, which are prepared by reacting 2,4- and optionally 2,6-diisocyanatotoluene or 1-methyl-2,4- and optionally 1-methyl-2,6-diisocyanatocyclohexane with substoichiometric amounts of trimethylolpropane or its mixtures with monomeric diols, such as the isomeric propanediols or butanediols, for example.
• lacquer polyisocyanates containing urethane groups in virtually monomer-free form is described for example in DE-A 109 01 96.
• lacquer polyisocyanates containing biuret groups include in particular those based on 1,6-diisocyanatohexane and prepared as described, for example, in EP-A 0 003505, DE-B 1 101 394, U.S. Pat. No. 3,358,010 or U.S. Pat. No. 3,903,127.
• the lacquer polyisocyanates containing isocyanurate groups include the trimers or mixed trimers of the diisocyanates exemplified above such as the isocyanurate-group-containing polyisocyanates based on TDI as described in GB-A 1 060 430, GB-A 1 506 373 or GB-A 1 485 564; and the mixed trimers of TDI with 1,6-diisocyanatohexane, which are described, for example, in DE-A 164 480 9 or DE-A 314 467 2.
• Preferred lacquer polyisocyanates containing isocyanurate groups are the aliphatic, aliphatic/cycloaliphatic and/or cycloaliphatic trimers or mixed trimers based on 1,6-diisocyanatohexane and/or isophorone diisocyanate that are obtained, for example, as described in U.S. Pat. No. 4,324,879, U.S. Pat. No. 4,288,586, DE-A310 026 2,DE-A310 026 3,DE-A303 386 0or DE-A314 467 2.
• lacquer polyisocyanates are those containing iminooxadiazinedione groups, which may be prepared as described, for example, in EP-A 798 299, EP-A 896 009, EP-A 962 454 and EP-A 962 455.
• Especially preferred starting polyisocyanates are urethane, uretdione, allophanate, biuret, isocyanurate and/or iminooxadiazinedione group-containing polyisocyanates exclusively containing aliphatically and/or cycloaliphatically bound NCO groups.
• Starting polyisocyanates A) preferably have an NCO group content of 5% to 25% by weight, an average NCO functionality of 2.0 to 5.0, preferably 2.8 to 4.0, and a residual monomeric diisocyanate content of below 1% by weight, preferably below 0.5% by weight.
• the starting polyisocyanates have a viscosity of 150 to 200,000 mPa ⁇ s at 23° C., measured using a rotational viscometer in accordance with DIN 53019.
• Preferred acrylate and/or methacrylate group-containing monoalcohols B) include the hydroxy-functional esters of acrylic and/or methacrylic acid.
• Suitable esters include hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate (isomer mixture formed in the addition reaction of propylene oxide with acrylic acid), hydroxypropyl methacrylate (isomer mixture formed in the addition reaction of propylene oxide with methacrylic acid) and butanediol monoacrylate.
• reaction products of the preceding hydroxy esters of acrylic or methacrylic acid with different amounts of cyclic lactones or monoepoxides.
• a preferred cyclic lactone is ⁇ -caprolactone and preferred monoepoxides are ethylene oxide, propylene oxide or mixtures thereof.
• hydroxyl-functional compounds B are also suitable as hydroxyl-functional compounds B) are the reaction products of glycidyl acrylate or glycidyl methacrylate with monocarboxylic acids, or the reaction products of acrylic or methacrylic acid with monoepoxides.
• Suitable compounds B) include allyl alcohol or its alkoxylation products, such as mono-, di- or polyethoxylated allyl alcohol. Preference, however, is given to the exclusive use of the previously described (meth)acrylate-functional alcohols as compounds B).
• non-functional, olefinically unsaturated monomers such as for example styrene, methyl methylacrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate and acrylonitrile etc., can also be added. These monomers do not react with the starting isocyanates in A) but can copolymerize later with the unsaturated groups of the alcohols B).
• the reaction of A) with B) can take place in the absence of solvent or in the presence of solvents.
• Suitable solvents are those which do not react with isocyanate groups or hydroxyl groups. Examples include aliphatic, cycloaliphatic and/or aromatic hydrocarbons such as alkylbenzenes, toluene and xylene; esters such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, n-hexyl acetate, 2-ethylhexyl acetate, ethyl propionate, butyl propionate, pentyl propionate, ethylene glycol monoethyl ether acetate and the corresponding methyl ether acetate; ethers such as ethylene glycol acetate monomethyl, monoethyl and monobutyl ether; ketones such as acetone, methyl ethyl ketone, methyl
• urethanization reaction A) and B) are reacted with one another in a ratio such that only some of the NCO groups of A) are consumed. It is preferred to use a quantity of component B) such that not more than 40 mole %, preferably not more than 30 mole %, more preferably not more than 25 mole % and most preferably not more than 20 mole %, based on the moles of isocyanate groups in starting polyisocyanates A), are converted to urethane groups.
• the urethanization may take place at room temperature (23° C.), but can also be carried out above or below this temperature. In order to accelerate the reaction it can be carried out at up to 160° C. Higher temperatures are not preferred, since an uncontrolled polymerization of the acrylate or methacrylate groups may occur.
• the unsaturated (meth)acrylate groups are not reacted by free-radical (co)polymerization until after urethanization has ended.
• Suitable initiators for carrying out the (co)polymerization of the unsaturated groups of unsaturated urethanized polyisocyanates C) and if need further unsaturated groups of non functional compounds are the known free-radical initiators based on azo or peroxide compounds which within the temperature range specified below possess a half-life whose duration is sufficient for the polymerization, i.e. a half-life of about 5 seconds to about 60 minutes.
• the initiators are used in amounts of 0.05% to 15%, preferably 0.1% to 10% and more preferably 0.2% to 8% by weight, based on the total amount of unsaturated compounds in B).
• urethane-modified polyisocyanate mixture C is heated to the desired polymerization temperature. Then the free-radical initiator is metered into the reaction mixture and the free-radical polymerization, which is initiated by the decomposition of the free-radical initiator, is carried out at the set polymerization temperature. This polymerization temperature can also be altered as desired in order to perform specific molecular weight adjustments. After the end of the polymerization, the reaction mixture is cooled to room temperature.
• the resulting polyacrylate-modified polyisocyanates of the invention are generally pale-colored viscous liquids or solutions if solvents were employed.
• additives such as PU catalysts, e.g., N,N-dimethylbenzylamine, N-methylmorpholine, zinc octoate, tin(II) octoate or dibutyltin dilaurate.
• PU catalysts e.g., N,N-dimethylbenzylamine, N-methylmorpholine, zinc octoate, tin(II) octoate or dibutyltin dilaurate.
• the polyacrylate-modified polyisocyanates of the invention constitute valuable raw materials for the preparation of binder compositions for producing polyurethane-based coating, adhesive or sealant compositions.
• the reactive isocyanate groups of the polyacrylate-modified polyisocyanates of the invention may be blocked with blocking agents and then used as crosslinkers in 1K (one-component) polyurethane (PU) coating compositions.
• Suitable blocking agents include ⁇ -caprolactam, butanone oxime, phenol and/or phenol derivatives, secondary amines, 3,5-dimethylpyrazole, alkyl malonates or monoalcohols.
• Suitable compounds having NCO-reactive groups are the known OH and/or NH-functional resins from coatings technology. Examples include polyesters, polyacrylates, polyurethanes, polyureas, polycarbonates or polyethers. Also suitable are hybrid resins or mixtures of different hydroxy-functional resins.
• the resins used are hydroxy-functional and/or amino-functional and may contain carboxylic and/or sulphonic acid groups or epoxid groups. It is also possible to use non-functional resins, which dry physically or oxidatively, alone or in combination with hydroxy-functional resins, as binder compounds and reaction partners for the polyisocyanate mixtures of the invention.
• These resins have hydroxyl contents of 0.5% to 15.0%, preferably 0.5% to 12.0%, more preferably 1.0% to 10.0% and most preferably 1.0% to 8.0% by weight, based on resin solids.
• the acid numbers of the solid resins are below 50 mg KOH/g, preferably below 30 mg KOH/g, more preferably below 20 mg KOH/g and most preferably below 15 mg KOH/g.
• the preceding resins based on addition polymer and/or polyester, particularly on polyacrylate, are of particular interest with regard to the level of requirements in the fields of automotive OEM, automotive refinish and large-vehicle finishing, general industrial coating, plastics coating, corrosion control, and wood and furniture coating. In the construction sector or for coating mineral substrates it is preferred to employ polyether-based resins.
• the equivalent ratio of free and blocked NCO groups to the NCO-reactive groups in the binders is 5:1 to 1:2, preferably 2:1 to 1:2, more preferably 1.5:1 to 1:1.5 and most preferably 1.2:1 to 1:1.2.
• the binder compositions have only a limited processing life of approximately 3 to 24 hours and are processed either as they are (transparent coating compositions), or preferably with the additional use of known additives. These optional additives can be added either to the mixture or to the individual components prior to their mixing.
• Suitable additives include solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, n-hexyl acetate, n-heptyl acetate, 2-ethylhexyl acetate, methoxypropyl acetate, methyl ethyl ketone, methyl isobutyl ketone, toluene, xylene, higher aromatics mixtures, white spirit and mixtures thereof.
• solvents such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, n-hexyl acetate, n-heptyl acetate, 2-ethylhexyl acetate, methoxypropyl acetate, methyl ethyl ketone, methyl isobutyl ketone, toluene
• plasticizers such as tricresyl phosphate, phthalic diesters and chlorinated paraffins
• pigments and fillers such as titanium dioxide, barium sulphate, chalk and carbon black
• catalysts such as N,N-dimethylbenzylamine, N-methylmorpholine, zinc octoate, tin(II) octoate and dibutyltin dilaurate
• flow control agents thickeners
• stabilizers such as substituted phenols
• organo-functional silanes as adhesion promoters
• light stabilizers and UV absorbers.
• light stabilizers are sterically hindered amines, as described for example in DE-A 2 417 353 and DE-A 2 456 864.
• Preferred light stabilizers are bis(1,2,2,6,6-pentamethylpiperid-4-yl) sebacate, bis(2,2,6,6-tetramethylpiperid-4-yl) sebacate, and bis(1,2,2,6,6-pentamethylpiperid-4-yl) n-butyl(3,5-di-tert-butyl-4-hydroxybenzyl) malonate.
• the moisture present in the fillers and pigments can be removed by drying beforehand or by the additional use of water absorbers, such as molecular sieve zeolites.
• the coatings obtained from the binder compositions of the invention can be dried at room temperature with no need for any increase in temperature to achieve the optimal properties mentioned at the outset.
• a temperature increase to about 60 to 100° C., preferably 60 to 80° C., for a period of 20 to 60 minutes is often advisable in order to shorten the drying time and cure time.
• the resulting coating films are notable for high hardness, good elasticity, excellent weathering stability and chemical resistance, and high gloss.
• Particularly the cure times, both for initial physical drying and for chemical crosslinking, are very short, i.e., shorter than when using non-polyacrylate-modified polyisocyanates, so that coated service articles are very rapidly resistant to solvents and chemicals and can be taken into service.
• the coating compositions employed in accordance with the invention are suitable in particular for the finishing of large vehicles, such as aircraft, railway coaches and trams and lorry bodies. Further preferred fields of use are automotive refinishing and the coating of plastics.
• the coating compositions are additionally suitable for corrosion control applications (such as the coating of bridges and power masts), wood and furniture coatings, general industrial coatings and automotive OEM coatings.
• Desmodur® HL BA Aromatic-aliphatic polyisocyanate based on toluene diisocyanate/hexamethylene diisocyanate (HDI), 60% in butyl acetate, NCO content 10.5%, available from Bayer MaterialScience AG, Leverkusen DE.
• Desmodur® IL BA Aromatic polyisocyanate based on toluene diisocyanate, 51% in butyl acetate, NCO content 8.0%, available from Bayer MaterialScience AG, Leverkusen DE.
• Desmoduro® 3200 Aliphatic, biuret group-containing polyisocyanate based on HDI, solvent-free, NCO content 23.0%, available from Bayer MaterialScience AG, Leverkusen DE.
• Desmoduro® N 3600 Low viscosity, isocyanurate group-containing polyisocyanate based on HDI, solvent-free, NCO content 23.0%, available from Bayer MaterialScience AG, Leverkusen DE.
• Desmoduro® N 75 BA Aliphatic, biuret group-containing polyisocyanate based on HDI, 75% in butyl acetate, NCO content 16.5%, available from Bayer MaterialScience AG, Leverkusen DE.
• Desmodur® XP 2410 Low-viscosity, iminooxadiazinedione group-containing polyisocyanate based on hexamethylene diisocyanate, solvent-free, NCO content 23.7%, available from Bayer MateriaiScience AG, Leverkusen DE.
• Peroxan® PO 49B tert-Butyl peroxy-2-ethylhexanoate, 49% in butyl acetate, available from Pergan GmbH, Bocholt DE.
• a 1-liter three-necked flask with stirrer, reflux condenser and dropping funnel was charged with the respective starting polyisocyanate and, when appropriate, butyl acetate as solvent, and this initial charge was heated to 130° C. under a nitrogen atmosphere. Then the unsaturated monoalcohol was metered in over a period of 10 minutes and the mixture was subsequently stirred further at 130° C. for 1 hour before the desired polymerization temperature (T) was set. When this temperature had been reached the polymerization initiator, Peroxan® PO 49B, was added in one portion, after which stirring took place at the set polymerization temperature for 1 hour. The mixture was then cooled to room temperature, giving the pale-colored, viscous polyisocyanates (PICs).
• PICs pale-colored, viscous polyisocyanates
• the varnishes were applied to glass plates at 23° C. and 50% relative humidity, dried both at room temperature and at 60° C. for 30 minutes, during which the drying rate (DIN 53 150) was determined, and then stored at room temperature for 7 days.
• the dry film thickness was 55 to 60 ⁇ m.

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• Chemical & Material Sciences (AREA)
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• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Polyurethanes Or Polyureas (AREA)
• Sealing Material Composition (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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