WO2022084253A1 - Revêtement supérieur en polyuréthane transparent à haute performance - Google Patents

Revêtement supérieur en polyuréthane transparent à haute performance Download PDF

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Publication number
WO2022084253A1
WO2022084253A1 PCT/EP2021/078816 EP2021078816W WO2022084253A1 WO 2022084253 A1 WO2022084253 A1 WO 2022084253A1 EP 2021078816 W EP2021078816 W EP 2021078816W WO 2022084253 A1 WO2022084253 A1 WO 2022084253A1
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weight
coating
composition
top coat
mpa
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PCT/EP2021/078816
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English (en)
Inventor
Stephen Glover
Alex COUPE
Alexander COWARD
Michael Byrne
Mark GATRELL
Urs Burckhardt
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Sika Technology Ag
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Publication of WO2022084253A1 publication Critical patent/WO2022084253A1/fr

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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
    • C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3253—Polyamines being in latent form
    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
    • C08G18/4233—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups derived from polymerised higher fatty acids or alcohols
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4808—Mixtures of two or more polyetherdiols
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • 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
    • C09D175/08—Polyurethanes from polyethers
    • E—FIXED CONSTRUCTIONS
    • E04—BUILDING
    • E04F—FINISHING WORK ON BUILDINGS, e.g. STAIRS, FLOORS
    • E04F15/00—Flooring
    • E04F15/02—Flooring or floor layers composed of a number of similar elements
    • E04F15/10—Flooring or floor layers composed of a number of similar elements of other materials, e.g. fibrous or chipped materials, organic plastics, magnesite tiles, hardboard, or with a top layer of other materials
    • E04F15/105—Flooring or floor layers composed of a number of similar elements of other materials, e.g. fibrous or chipped materials, organic plastics, magnesite tiles, hardboard, or with a top layer of other materials of organic plastics with or without reinforcements or filling materials

Definitions

  • the invention relates to transparent one-part moisture curing polyurethane top coats of high solids content, low viscosity and high performance with regard to strength, elasticity, interlayer adhesion and durability against UV, heat and hydrolysis, and their use on elastic pigmented polyurethane floor systems, particularly for outdoor uses on balconies, terraces and footbridges.
  • Transparent top coats for elastic outdoor polyurethane floors are known, for example for the application on balconies. Particularly easy to apply are so-called one- part products, which do not need a metering and mixing step before the application.
  • State-of-the-art one-part transparent top coats are typically either solventbased or water-based, with a solids content in the range of 40 to 60 weight-%. They suffer from limited elasticity and limited stability against hydrolysis. In particular they have insufficient interlayer adhesion after long-term exposure to standing water, also called ponding water. Solvent-based products have further limitations, such as harsh hazard labelling and intense odour, whereas water-based products suffer from insufficient cure speed under cold and humid conditions, so that their use is seasonally restricted.
  • Pigmented one-part moisture-curing polyurethane coatings with reliable curing and their use as so-called liquid-applied membranes for the waterproofing of roofs are known, for example from US 9,752,054.
  • US 8,178,167 describes similar coatings for the use on floors. These coatings are based on polyoxypropylene glycol polyols and isophorone diisocyanate in combination with special aldimines. They have a limited tensile strength, and their durability against UV and hydrolysis is limited, particularly when they are used in thin layers. Summary of the invention
  • the task of this invention is to provide an elastic coating with good application properties at high solids content, high strength and durability at high elasticity and high stability against UV and hydrolysis, suitable for the use as transparent top coat on elastic polyurethane floors for outdoor use.
  • the one-part moisture curing polyurethane composition according to claim 1. It comprises at least one isocyanate-functional polymer with an NCO-content in the range of 5 to 10 weight-% in relation to the total polymer, obtained from the reaction of at least one aliphatic diisocyanate, preferably isophorone diisocyanate, with at least one polyol selected from the group consisting of poly(oxy-1 ,4-butylene) diols, aliphatic polycarbonate diols based on a linear diol and amorphous dimer fatty acid based polyester diols, and at least one aldimine of the formula (I).
  • This combination enables compositions of low odour with a low viscosity, a good shelf life stability, good mechanical properties and a good UV resistance.
  • the inventive composition is not water-based and has preferably a very low content of low boiling organic diluents. It is low viscous and can be easily applied in a thin layer, suitable as top coat onto elastic polyurethane floors. It shows a long open time and cures fast and reliably to a non-tacky film at ambient temperatures, also under cold and humid conditions. It can be formulated without pigments and fillers to form a transparent film after curing. In cured state, it shows a particularly high tensile strength at high elogation, together with a high scratch and abrasion resistance and a very good weathering resistance, particularly in terms of UV light, heat and water-exposure, with particularly low yellowing.
  • isocyanate-functional polymers based on poly(oxy-1 ,4- butylene) diols. These compositions show a surprisingly good interlayer adhesion on elastic pigmented polyurethane floors, even after prolonged exposure to standing water, which is particularly difficult to achieve.
  • the inventive composition is particularly suitable for outdoor use as transparent top coat on elastic polyurethane floors, which are exposed to harsh environmental conditions, for example on balconies, terraces and footbridges.
  • Other aspects of the invention are described in other independent claims. Preferred aspects of the invention are described in dependent claims.
  • the subject of the present invention is a one-part moisture-curing polyurethane composition, comprising
  • At least one isocyanate-functional polymer an NCO-content in the range of 5 to 10 weight-% in relation to the total polymer, obtained from the reaction of at least one aliphatic diisocyanate with at least one polyol selected from the group consisting of poly(oxy-1 ,4-butylene) diols, aliphatic polycarbonate diols based on a linear diol and amorphous dimer fatty acid based polyester diols, optionally in combination with at least one chain extender which is a diol with two primary hydroxyl groups and a molecular weight in the range of 60 to 150 g/mol, and
  • A is a n-valent aliphatic, cycloaliphatic or arylaliphatic hydrocarbyl moiety possibly containing ether oxygen with a molecular weight in the range of 84 to 500 g/mol
  • R 1 and R 2 are the same or different Ci to C4 alkyl, or are joined together to form a C4 to Ce alkylene
  • R 3 and R 4 are the same or different Ci to Cs alkyl optionally containing ether oxygen, or are joined together to form a C4 to Ce alkylene optionally containing ether oxygen.
  • the term facedone-part moisture-curing polyurethane composition refers to a polyurethane composition, which is stored in a single moisture-tight container before use, has shelf life stability and cures when exposed to moisture. Such one-part compositions are also referred to as locallyone-component”, possiblyone-pack“ orarrangingsingle-pack“ compositions.
  • the term crizo-fite composition refers to the ability of a composition to be stored at room temperature in a suitable container under exclusion of moisture for a certain time interval, in particular several months, without undergoing significant changes in application or end-use properties.
  • ..molecular weight refers to the molar mass (g/mol) of a molecule or a moiety of a molecule.
  • ..average molecular weight refers to the number average molecular weight (Mn) of an oligomeric or polymeric mixture of molecules or moieties of molecules. It is determined by means of gel permeation chromatography (GPC) against polystyrene as the standard, particularly with tetra- hydrofuran as the mobile phase and a refractive index detector.
  • GPC gel permeation chromatography
  • the term refers to the mass fraction of a constituent of a composition based on the entire composition, unless stated otherwise.
  • the terms ..weight” and ..mass” are used synonymously in this document.
  • ..room temperature refers to a temperature of 23°C.
  • the one-part moisture-curing polyurethane composition comprises at least one isocyanate-functional polymer obtained from the reaction of at least one aliphatic diisocyanate with at least one polyol selected from the group consisting of poly- (oxy-1 ,4-butylene) diols, aliphatic polycarbonate diols based on a linear diol and amorphous dimer fatty acid based polyester diols, optionally in combination with at least one chain extender which is a diol with two primary hydroxyl groups and a molecular weight in the range of 60 to 150 g/mol.
  • the at least one aliphatic diisocyanate is preferably 1 ,6-hexane diisocyanate (HD I), isophorone diisocyanate (IPDI), methyldiisocyanatocyclohexane (HeTDI or HTDI), perhydro-4.4'-diphenylmethane diisocyanate (H12MDI or HMDI) or m- or p- xylene diisocyanate (XDI). Particularly preferred is isophorone diisocyanate (IPDI). This aliphatic diisocyanate enables a particuarly good shelf life stability together with a low viscosity and a high strength at high elongation.
  • the at least one polyol has preferably an average OH-number in the range of 50 to 180 mg KOH/g, more preferably 80 to 180 mg KOH/g, particularly 100 to 160 mg KOH/g.
  • a preferred aliphatic polycarbonate diol based on a linear diol is Eternacoll® UH- 100 (from UBE).
  • a preferred amorphous dimer fatty acid based polyester diol is Priplast® 1838 or Priplast® 3238 (from Croda). These diols enable a high hydrophobicity and a low viscosity.
  • Most preferred polyols are poly(oxy-1 ,4-butylene) diols.
  • a poly(oxy-1 ,4-butylene) diol is a polyether diol with 1 ,4-butyleneoxy units. Such a diol is also called a polytetramethylene ether glycol (PTMEG or PTMG). It enables a good UV stability and a high resistance against hydrolysis together with a surprisingly good interlayer adhesion after long term water exposure if the composition is used as top coat.
  • PTMEG polytetramethylene ether glycol
  • the at least one polyol is a poly(oxy-1 ,4-butylene) diol or a mixture of poly(oxy-1 ,4-butylene) diols.
  • the isocyanate-functional polymer is obtained from the reaction of isophorone diisocyanate with a poly(oxy-1 ,4-butylene) diol or a mixture of poly- (oxy-1 ,4-butylene) diols, optionally in combination with at least one chain extender.
  • the poly(oxy-1 ,4-butylene) diol or a mixture of poly(oxy-1 ,4-butylene) diols has an overall average OH-number in the range of 80 to 180 mg KOH/g, preferably 100 to 160 mg KOH/g. If a mixture of two or more poly(oxy-1 ,4-butylene) diols are used, the overall average OH-number is the average of the OH-numbers of the diols in the mixture.
  • the poly(oxy-1 ,4-butylene) diol is preferably selected from the group consisting of
  • Such diols are commercially available, for example as Terathane® 650, Teratha- ne® 1000, Terathane® 1400, Terathane® 1800 or Terathane® 2000 (all from Invista), or as polyTHF 650, polyTHF 1000, polyTHF 1400, polyTHF 1800 of polyTHF 2000 (all fom BASF).
  • Preferred chain extenders are 1 ,2-ethanediol, 1 ,3-propanediol, 1 ,4-butanediol, 1 ,5- pentanediol, 1 ,6-hexanediol, 1 ,3-cyclohexanedimethanol, 1 ,4-cyclohexanedime- thanol or diethylene glycol, or a combination thereof. Most preferred is 1 ,4-butane- diol.
  • the amount of chain extender preferably 1 ,4-butanediol, is in the range of 1 to 8 weight parts, preferably 2 to 6 weight parts, per 100 weight parts of the poly(oxy-1 ,4-butylene) diols in the isocyanate-functional polymer.
  • the isocyanate-functional polymer has an NCO-content in the range of 5 to 10 weight-% in relation to the total polymer. Preferably, the NCO-content is in the range of 6 to 8 weight-%. If the polymer contains a diluent, the diluent is thereby not considered as part of the polymer.
  • the isocyanate-functional polymer is preferably prepared by combining the polyol, optionally the chain extender and a molar excess of the aliphatic diisocyanate in the absence of moisture at a temperature in the range of 20 to 160°C, preferably 40 to 140°C, optionally in the presence of a suitable catalyst, and optionally in the presence of a diluent.
  • Preferred is a molar NCO/OH ratio between the aliphatic diisocyanate, the polyol and the optionally present chain extender in the range of 1 .5/1 to 10/1 , preferably 1 .8/1 to 8/1 .
  • the molar NCO/OH ratio is in the range of 1 .8/1 to 2.3/1 , preferably 1 .8/1 to 2/1 .
  • Such a polymer is particularly easy available.
  • the molar NCO/OH ratio is in the range of 3/1 to 10/1 , preferably 3/1 to 8/1 , and most of the excess isophorone diisocyanate is removed from the isocyanate-functional polymer after the reaction, preferably by distillation, preferably by thin film distillation or short path distillation under vacuum.
  • the inventive composition has a content of the isocyanate-functional polymer of at least 30 weight-%, preferably at least 35 weight-%, in relation to the total composition.
  • the inventive composition further comprises at least one aldimine of the formula (I).
  • A is selected from the group consisting of 1 ,6-hexylene, 2-methyl-1 ,5- pentylene, (1 ,5,5-trimethylcyclohexane-1 -yl)methane-1 ,3, 4(2)-methyl-1 ,3-cyclo- hexylene, 1 ,3-cyclohexylene-bis(methylene), 1 ,4-cyclohexylene-bis(methylene), 1 ,3-phenylene-bis(methylene), 1 ,2-cyclohexylene, 1 ,3-cyclohexylene, 1 ,4-cyclo- hexylene, methylene-bis(cyclohexan-4-yl), (bicyclo[2.2.1 ]heptane-2,5(2,6)-diyl)- dimethylene, (tricyclo[5.2.1 ,0 2 ’ 6 ]decane-3(4),8(9)-d
  • aldimines of the formula (I) are derived from hexane-1 ,6-diamine, 2-methyl- pentane-1 ,5-diamine, 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine), 4(2)-methylcyclohexane-1 ,3-diamine, 1 ,3- or 1 ,4-bis(aminomethyl)cyclo- hexane, 1 ,3-bis(aminomethyl)benzene, 1 ,2- or 1 ,3- or 1 ,4-diaminocyclohexane, bis(4-aminocyclohexyl)methane, 2,5(2,6)-bis-(aminomethyl)bicyclo[2.2.1 ]heptane, 3(4),8(9)-bis(aminomethyl)-tricyclo[5.2.1 .0 2 ’ 6 ]decane, polyoxypropylene diamines with an average molecular
  • A is 1 ,6-hexylene, (1 ,5,5-trimethylcyclohexane-1 -yl)methane-1 ,3, methylene-bis(cyclohexan-4-yl) or trimethylolpropane or glycerine started tris(o- polyoxypropylene) with an average molecular weight Mn in the range of 330 to 500 g/mol.
  • R 1 and R 2 are both methyl.
  • R 3 and R 4 are either both a methoxyethyl group, or are joined together to form a 3-oxa-1 ,5-pentylen or a 2,4-dimethyl-3-oxa-1 ,5-pentylene group, which forms together with the nitrogen atom, to which R 3 and R 4 are bonded, a morpholine or a 2,6-dimethylmorpholine ring.
  • R 1 and R 2 are both methyl and R 3 and R 4 are either both a methoxyethyl group or are joined together to form a 3-oxa-1 ,5-pentylen or a 2,4- dimethyl-3-oxa-1 ,5-pentylene group.
  • R 3 and R 4 are joined together to form a 3-oxa-1 ,5-pentylen group, which is part of a morpholine ring.
  • the at least one aldimine of the formula (I) is selected from the group consisting of N,N'-bis(2,2-dimethyl-3-(N-morpholino)propylidene)-1 ,6-hexanedi- amine, N,N'-bis(2,2-dimethyl-3-(N-morpholino)propylidene)-3-aminomethyl-3,5,5- trimethylcyclohexylamine, N,N'-bis(2,2-dimethyl-3-(N-morpholino)propylidene)-4,4'- methylene-bis(cyclohexylamine), N,N',N"-tris(2,2-dimethyl-3-(N-morpholino)pro- pylidenejpolyoxypropylene triamine with an average molecular weight Mn in the range of 800 to 950 g/mol and mixtures thereof.
  • Particularly preferred is a mixture of N,N'-bis(2,2-dimethyl-3-(N-morpholino)propyli- dene)-3-aminomethyl-3,5,5-trimethylcyclohexylamine and N,N',N"-tris(2,2-dime- thyl-3-(N-morpholino)propylidene)polyoxypropylene triamine.
  • the inventive composition contains at least 12 weight-%, preferably at least 15 weight-%, of aldimines of the formula (I) in relation to the total composition.
  • the inventive composition contains less than 25 weight-%, preferably less than 20 weight-%, of aldimines of the formula (I) in relation to the total composition.
  • the inventive composition preferably contains such an amount of aldimines, that the ratio between the total number of aldimine groups to the total number of isocyanate groups is in the range of 0.5 to 1 , preferably 0.6 to 1 , more preferably 0.7 to 1.
  • the inventive composition contains at least one further ingredient selected from the group consisting of oligomeric diisocyanates, diluents, catalysts, stabilizers and defoamers.
  • the inventive composition preferably contains at least one oligomeric diisocyanate, preferably an oligomer of hexamethylene-1 ,6-di isocyanate (HDI) and/or an oligomer of isophorone diisocyanate ( I PD I), particularly an isocyanurate of IPDI.
  • oligomeric diisocyanate can help to achieve a high strength.
  • its use is limited to a certain extent, as it can cause a dramatic reduction of elongation.
  • Suitable diluents are organic solvents, particularly acetone, methyl ethyl ketone, methyl n-propyl ketone, diisobutyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, methyl isoamyl ketone, acetyl acetone, mesityloxide, cyclohexanone, methylcyclohexanone, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, tert, butyl acetate, 1 -methoxy-2-propylacetate, n-butyl propionate, ethyl-3-ethoxy propionate, diethyl malonate, diisopropyl ether, dibutyl ether, ethylene glycol di- ethylether, ethylene glycol monopropylether, ethylene glycol mono-2-ethylhe
  • Preferred diluents are those with a boiling point at atmospheric pressure of 200°C or more. Such high boiling diluents slowly evaporate from the cured composition at ambient temperatures, increasing the strength with hardly any effect on the elongation.
  • a particularly preferred high boiling diluent is 2,5,7, 10-tetraoxaundecane (TOU), which has particularly high diluting power and low smell.
  • TOU 2,5,7, 10-tetraoxaundecane
  • the inventive composition has a content of diluents with a boiling point below 200°C at atmospheric pressure of below 5 weight-%, preferably below 2.5 weight-%, more preferably below 1 weight-%, in relation to the total composition.
  • Suitable catalysts are catalysts for the acceleration of the reaction of isocyanate groups, particularly metal catalysts, preferably dialkyltin complexes, in particular dibutyltin or dioctyltin carboxylates or acetoacetonates such as dibutyltindilaurate (DBTDL), dibutyltindi(acetoacetate) (DBT(acac)2) or dioctyltindilaurate (DOTDL), or amine catalysts, preferably tertiary aminoethers, in particular 2, 2'-dimorpholino- diethylether (DMDEE).
  • DBTDL dibutyltindilaurate
  • DBT(acac)2 dibutyltindi(acetoacetate)
  • DOTDL dioctyltindilaurate
  • amine catalysts preferably tertiary aminoethers, in particular 2, 2'-dimorpholino- diethylether (DMDEE).
  • Suitable catalysts are also catalysts for the acceleration of aldimine hydrolysis, particularly acid catalysts, particularly carboxylic acids or sulfonic acids, preferably aromatic carboxylic acids such as benzoic acid or salicylic acid.
  • Preferred stabilizers are UV stabilizers and or heat stabilizers, particularly UV absorbers such as 2-cyano-3,3-diphenylacrylic acid ethyl ester, or hindered amine light stabilisers (HALS), such as bis(1 ,2,2,6, 6-pentamethyl-4-piperidyl) sebacate.
  • UV absorbers such as 2-cyano-3,3-diphenylacrylic acid ethyl ester
  • HALS hindered amine light stabilisers
  • the inventive composition contains at least one stabilizer.
  • the inventive composition contains at least one defoamer.
  • the inventive composition may further contain the following ingredients:
  • additives such as wetting agents, flow enhancers, leveling agents, deaerating agents, antioxidants or biocides,
  • plasticizers particularly phthalates, particularly diisononyl phthalate (DINP) or diisodecyl phthalate (DIDP), hydrogenated phthalates, particularly hydrogenated DINP, which is diisononyl-1 ,2-cyclohexane dicarboxylate (DINCH), terephthalates, particularly bis(2-ethylhexyl) terephthalate or diisononyl terephthalate, hydrogenated terephthalates, particularly bis(2-ethylhexyl)-1 ,4-cyclo- hexane dicarboxylate, trimellitates, adipates, particularly dioctyl adipate (DOA), azelates, sebacates, citrates, benzoates, glycol ether, glycol esters, organic sulfonates or phosphates, particularly diphenylcresyl phosphate (DPK), polybutenes, polyisobutenes or plastic
  • - fillers such as ground or precipitated calcium carbonates (chalk), which are optionally surface coated with a fatty acid such as stearate, barium sulfate (barytes), slate, silicates (quartz), magnesiosilicates (talc) or alumosilicates (clay, kaolin), dolomite, mica, glass bubbles, silicic acid, particularly highly dispersed silicic acids from pyrolytic processes (fumed silica), carbon black, microspheres, pigments, particularly titanium dioxide or iron oxides, or flameretarding fillers such as aluminium hydroxides, particularly aluminium trihydroxide (ATH), magnesium dihydroxide, antimony trioxide, antimony pentoxide, boric acid, zinc borate, zinc phosphate, melamine borate, melamine cyanurate, ethylenediamine phosphate, ammonium polyphosphate, di-melamine orthophosphate, di-melamine pyrophosphate, hexabromo
  • fibres particularly glass fibres, carbon fibres, metallic fibres, ceramic fibres, plastic fibres, particularly polyamide fibres or polyethylene fibres, or natural fibres such as wool, cellulose, hemp or sisal,
  • nanofillers such as graphene or carbon nanotubes
  • - drying agents particularly molecular sieves, calcium oxide, highly reactive isocyanates such as p-tosylisocyanate, mono-oxazolidines such as Incozol® 2 (from Incorez) or orthoformic acid ester,
  • organoalkoxy silanes such as 3-glycidoxy- propyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, (meth)acrylosilanes, anhydridosilanes, carbamatosilanes, alkylsilanes or iminosilanes, or oligomers thereof, or titanates,
  • - natural resins fats or oils such as rosin, shellac, linseed oil, castor oil or soybean oil
  • - non-reactive polymers particularly homo- or copolymers of unsaturated monomers, particularly ethylene, propylene, butylene, isobutylene, isoprene, vinylacetate or alkyl(meth)acrylates, preferably polyethylene (PE), polypropylene (PP), polyisobutylene, ethylenevinyl acetate copolymers (EVA) or atactic poly-a- olefins (APAO).
  • PE polyethylene
  • PP polypropylene
  • EVA ethylenevinyl acetate copolymers
  • APAO atactic poly-a- olefins
  • the inventive composition is free of pigments, fillers, fibers and dyes. This enables a transparent look.
  • Such a composition is particularly suitable for the use as transparent top coat.
  • the inventive composition has a low amount of plasticizers, preferably below 10 weight-%, more preferably below 5 weight-%, particularly below 2 weight-%, in relation to the total composition.
  • a preferred inventive composition comprises in relation to the total composition:
  • the inventive composition has an overall content of isocyanate groups in the range of 2.5 to 6 weight-%, preferably 2.8 to 5 weight-%, more preferably 3 to 4.5 weight-%, in relation to the total composition.
  • the inventive composition has a low viscosity.
  • the viscosity at 20°C is less than 2'000 mPa s, preferably less than 1'500 mPa s, particularly less than 1'000 mPa s, determined with a Rotothinner type viscometer with the spherical spindle DV2011 at 500 rpm.
  • Such a composition is particularly easy to apply as coating, particularly as top coat in a thin layer. With a too high viscosity, it is not possible to apply thin layers such as 0.1 mm or less
  • the inventive composition is preferably prepared by mixing all ingredients under exclusion of moisture to obtain a macroscopically homogeneous fluid and stored in a moisture-tight container at ambient temperatures before use.
  • a suitable moisture-tight container consists preferably of an optionally coated metal or plastic. It is preferably a bucket, a barrel, a hobbock, a bag, a sausage, a can or a bottle. With suitable packaging and storage, the composition shows long shelf life stability, typically several months up to one year or more.
  • the inventive composition is preferably applied in a thin layer and cured by contact with moisture, especially atmospheric moisture.
  • moisture especially atmospheric moisture.
  • it is applied by spraying or by a brush or a roller or by pouring onto the substrate, optionally followed by spreading evenly with a suitable tool, such as a squeegee, a toothed trowel, a spatula, a roller, a brush or a draw down bar.
  • the process of curing begins when the composition is applied and gets in contact with moisture, especially atmospheric moisture.
  • the isocyanate groups react under the influence of moisture with the hydrolyzing aldimine groups.
  • the composition cures to form an elastic coating.
  • an aldehyde of the formula particularly 2,2-dimethyl-3-(N-morpholino)propanal, is released, which is of low odour and partly remains in the cured coating.
  • the inventive composition is preferably applied at ambient conditions, preferably in a temperature range of 0 to 45°C, preferably 5 to 40°C, in a layer thickness in the range of 0.05 to 1 mm onto at least one substrate.
  • Open time is the time period, within which the freshly applied composition can be processed or reworked without any negative effect.
  • a non-tacky elastic coating is formed, which is free of bubbles, also when cured at humid conditions.
  • Another subject of the invention is a coating, which is obtained from the inventive composition after its contact with moisture.
  • the inventive coating has a high tensile strength at high elongation.
  • inventive coating has a tensile strength of at least 8 MPa, preferably at least 12 MPa, and a high elongation at break of at least 150%, preferably at least 200% determined according to EN ISO 527-3, preferably with bar shaped test pieces of 100 x 25 x 0.5 mm at a crosshead speed of 180 mm/min.
  • the barshaped test items are preferably made by applying the liquid composition with a drawdown bar in the desired layer thickness onto a teflon substrate, from which it can be removed when cured, and left to cure 24 hours in normal climate, followed by 72 hours in an oven with 60°C and another 24 hours in normal climate and punching the bar-shaped test items from the film.
  • there is more than one test item punched from the film and tested as the values for the tensile strength and the elongation at break are the average of the data of several test items.
  • the coating shows good resistance against mechanical attack, particularly a high scratch and abrasion resistance.
  • the coating further shows a high tolerance for movements of the underlying floor, for example crack movements in the underlying substrate, vibrations of the floor or some tensions caused by a shrinkage induced by the curing process.
  • the inventive coating is improous for the use on a floor, on a roof, under ceramic tiles, for example in wet rooms or kitchens, as well as in sumps, channels, shafts, silos, tanks or wastewater treatment plants. Preferred is the use on a floor.
  • Suitable substrates, onto which the inventive composition can be applied, are particularly
  • PCC polymer modified cement
  • ECC epoxy modified cement
  • metals and alloys such as aluminium, copper, iron, steel, nonferrous metals, including surface-finished metals and alloys, such as galvanized metals or chrome-plated metals;
  • plastics such as hard or soft PVC, polycarbonate, polystyrene, polyester, polyamide, PMMA, ABS, SAN, epoxide resins, phenolic resins, PUR, POM, TPO, PE, PP, EPM or EPDM, in untreated form or surface-treated by means of plasma, corona or flame;
  • - fibre reinforced plastics such as carbon fibre reinforced plastics, glass fibre reinforced plastics or sheet moulding compounds
  • - insulating foams particularly out of EPS, XPS, PUR, PIR, rock wool, glass wool or foamed glass;
  • substrates are optionally pre-treated before the application of the composition, particularly by a physical and/or chemical cleaning process or by the application of an activator or primer.
  • the inventive coating is transparent. It has preferably an absorption value of less than 20, preferably less than 15, more preferably less than 10, determined by a spectrophotometer with D65 artificial light in a layer thickness of 0.1 mm applied on glass. Such a coating is transparent. Through such a coating, the color and structure of an underlying substrate is clearly visible.
  • Such a coating is particularly suitable as transparent top coat for elastic polyurethane floors, particularly polyurethane floors which are exposed to harsh outdoor conditions with high UV load and ponding water.
  • the inventive coating has a particularly high UV stability. Preferably, it shows no yellowing or only very slight yellowing in a QUV accelerated wheathering tester in alternating cyles of 8 hours UV radiation at 70°C followed by 4 hours moisture at 50°C after 1000 h exposure to UV-A or UV-B radiation.
  • the inventive coating is applied as a top coat onto a pigmented polyurethane floor coating.
  • the pigmented polyurethane floor coating is preferably outdoor, particularly on a balcony, a terrace, a footbridge or a staircase.
  • the top coat has a layer thickness in the range of 0.05 to 1 mm, more preferably 0.07 to 0.8 mm, particularly 0.08 to 0.5 mm.
  • the pigmented polyurethane floor coating is highly elastic and has a high resistance against UV. Preferably, it has an elongation at break of at least 150%, preferably at least 180%, determined at 23°C according to EN ISO 527-3.
  • a polyurethane floor has high crack-bridging properties.
  • the top coat needs to be a highly elastic material as well.
  • a particularly suitable pigmented polyurethane floor coating is SikafloohMOO N elastic, Sikafloor®-405, Sikafloor®-420 or Sikafloor®-425 (all from Sika), particularly Sikafloor®-420.
  • the pigmented polyurethane floor coating is broadcasted with colored flakes or with quartz sand.
  • the inventive coating is applied onto the pigmented polyurethane coating including the flakes or the sand particles.
  • the use of colored flakes gives a decorative finish with a patchy look, whereas the use of quartz sand gives a rough surface with a particularly good slip resistance. If a decorative colored quartz sand is used, the use of a transparent top coat enables a particularly aesthetic look.
  • the inventive coating is part of a floor system comprising
  • the substrate is particularly concrete, optionally pretreated by means of grinding, sandblasting or shot peening, or mortar, cement screed, fiber cement, brick, gypsum, natural stone such as granite or marble, asphalt or repair or leveling compounds based on PCC (polymer modified cement mortar) or ECC (epoxy resin- modified cement mortar).
  • PCC polymer modified cement mortar
  • ECC epoxy resin- modified cement mortar
  • a suitable primer is a polyurethane or an epoxy resin composition. It serves particularly to solidify and level out the substrate, to close any pores and to ensure a good adhesion to the next coating layer.
  • a particularly suitable primer is Sika- floor®-407 (from Sika).
  • the primer is preferably applied in an amount of 0.1 to 0.5 kg/m 2 .
  • the pigmented polyurethane floor coating is preferably highly elastic and UV stable. It is preferably applied by spraying or pouring onto the substrate or the at least partly cured primer or undercoat, optionally followed by spreading evenly to the desired layer thickness, which is preferably in the range of 0.3 to 2 mm, more preferably 0.4 to 1 .5 mm, particularly 0.5 to 1 mm, with a suitable tool, such as a squeegee, a toothed trowel, a spatula, a roller, a brush or a draw down bar. It can be obtained by moisture-curing a one-part composition or by mixing the components of a multi-part composition shortly before the application. Preferrend is the moisture-curing of a one-part composition.
  • the pigmented polyurethane floor coating can be applied in one or in more than one layer, preferably in one or two layers.
  • the surface of the pigmented polyurethane floor coating is broadcasted with colored flakes or with quartz sand.
  • the colored flakes are particularly vinyl flakes in a different color shade than the pigmented polyurethane coating. They are sprinkled onto the freshly applied coating to provide an aesthetically patterned surface.
  • the quartz sand is optionally a colored quarz sand. Its particle size is preferably in the range of 0.1 to 1 mm.
  • the sand is sprinked onto the freshly applied pigmented polyurethane coating in excess. After curing, the excess sand is removed and a rough surface with protruding grains of sand embedded in the coating is obtained. Such a surface has particularly good non-slip properties.
  • the sandy surface is being overcoated with a top coat, which prevents the sand particles from breaking out and eases the cleaning of the floor surface.
  • the inventive coating is applied as top coat onto the at least partly cured pigmented polyurethane floor coating, which optionally contains colored flakes or quartz sand.
  • it is applied with a roller in one or two layers, preferably in one layer.
  • the top coat has a layer thickness in the range of 0.05 to 1 mm, more preferably 0.07 to 0.8 mm, particularly 0.08 to 0.5 mm.
  • the top coat is transparent.
  • Such a transparent top coat gives a highly aesthetic finish on the surface of the floor system with a smooth, easy to clean elastic surface of high robustness against mechanical, UV or water attack.
  • the top coat shows a particularly good interlayer adhesion after exposure to long term standing water.
  • the top coat ensures an even, closed surface, through which the flakes or the sand are still clearly visible and prevents the flakes or sand particles from being broken out.
  • the floor system is preferably applied on a balcony, a terrace, a footbridge or a staircase. It is particularly suitable for outdoor use.
  • An example of an inventive floor system is a system build-up consisting of
  • the pigmented polyurethane coating which is 1 kg/m 2 of Sikafloor®-420 (from Sika), broadcasted with colored flakes,
  • the floor system is not only covering a floor, but also has to prevent a built structure below the floor from water attack.
  • a preferred undercoat for this use is preferably reinforced with a fibre reinforcement mesh, such as a non-woven glass fibre mesh.
  • a fibre reinforcement mesh such as a non-woven glass fibre mesh.
  • Such a fibre mesh is preferably rolled into the freshly applied, still liquid undercoat.
  • the undercoat is preferably also a pigmented polyurethane coating, of which the requirements regarding abrasion resistance are lower compared to the pigmented polyurethane floor coating, which is in contact with the top coat.
  • An example of a floor system of this kind is a system build-up consisting of
  • the pigmented polyurethane floor coating which is 1 kg/m 2 of Sikafloor®-420 (from Sika), broadcasted with colored flakes,
  • Such a floor system is easy to apply at ambient outdoor conditions, with low odor and low emission of low boiling organic solvents and a fast, reliable curing. It combines high crack-bridging properties with a robust, scratch- and abrasion- resistant and highly aesthetic transparently sealed surface, which resists harsh outdoor conditions without cracking, yellowing, softening or loss of interlayer adhesion.
  • Another subject of the invention is a floor system for outdoor use comprising
  • the base coat is preferably a pigmented polyurethane floor coating as described before.
  • the top coat is preferably obtained by an aliphatic polyurethane composition, which is free of aromatic constituents in the polymer. Such a composition enables a high UV stability, which is beneficial for outdoor use.
  • the top coat is preferably a coating as described before, which is obtained from the inventive one-part moisture-curing polyurethane composition.
  • the top coat is preferably transparent.
  • Normal climate means a temperature of 23 ⁇ 1 °C and a relative atmospheric moisture of 50 ⁇ 5% and is abbreviated with "NC”.
  • Chemical substances not otherwise specified are from Sigma-Aldrich Chemie GmbH.
  • the viscosity was measured at a temperature of 20°C with a Rotothinner type viscometer with the spherical spindle DV2011 at 500 rpm.
  • the amine content (total content of free amines and blocked amines, i.e. aldimino groups) of the prepared aldimines was determined by titration (with 0.1 N HCIO4 in acetic acid against cristal violet) and is given in mmol N/g.
  • Aldimine A1 N,N'-bis(2,2-dimethyl-3-(N-morpholino)propylidene)-3-aminomethyl- 3,5,5-trimethylcyclohexylamine
  • Aldimine A2 N,N',N"-tris(2,2-dimethyl-3-(N-morpholino)propylidene) polyoxypropylene triamine
  • PC/PE-2000 polycarbonate polyester copolymer diol OH-number ca.
  • PPG-1000 polyoxy-1 ,2-propylene glycol diol, OH-number ca. 112 mg KOH/g (Voranol® 1010L, from Dow)
  • PCcy-900 (Eternacoll® UM-90 (1/1 ), from UBE), 4.0 g 1 ,4-butanediol and
  • PE-al-2000 (Kuraray® Polyol P-2030, from Kuraray)
  • 2.0 g 1 ,4-butanediol and 32.1 g isophorone diisocyanate (Vestanat® IPDI, from Evonik) were reacted in the presence of 0.1 g dibutyltin dilaurate and 50.9 g 2,5,7, 10-tetraoxaundecane (TOU, from Univar).
  • TOU 2,5,7, 10-tetraoxaundecane
  • the product obtained had an NCO-content of 3.2 weight-% and a viscosity at 20°C of 1'360 mPa s.
  • PE-ar-2000 (Stepanpol® PH-56, from Stepan), 2.0 g 1 ,4-butanediol and
  • compositions C1 to C9 Each composition was prepared by mixing the ingredients given in Table 2 in the given amounts (weight parts) in a centrifugal mixer (SpeedMixerTM DAC 150, FlackTek Inc.) under exclusion of moisture, and stored in a moisture-tight container. The compositions were tested as follows:
  • the viscosity was measured as previously described at 20°C after storing the moisture-tight container in normal climate for one day.
  • a cured film with a thickness of 0.5 mm was made of each composition.
  • the film was cured for 24 h in normal climate, then placed in an oven at 60°C for 72 h and left again in normal climate for 24 h.
  • Bar-shaped test items with a length of 100 mm and a width of 25 mm were punched from the film and the tensile strength and the elongation at break were determined according to EN ISO 527-3 at a crosshead speed of 180 mm/min.
  • the UV resistance was determined with coated aluminium panels in a QUV accelerated wheathering tester in alternating cyles of 8 hours UV radiation at 70°C followed by 4 hours moisture at 50°C.
  • the aluminium panels were coated with a layer of 1 mm of each composition.
  • the test samples were judged after 1000 h exposure to either UV-A radiation (UV-A 340 lamp) or UV-B radiation (UV-B 313 lamp), wherein
  • Values of 3 or higher indicate that the coating is not UV stable enough to be beneficial for outdoor use.
  • the interlayer adhesion was judged by coating a freshly cured film with a thickness of 1 mm of a pigmented polyurethane coating (Sikafloor®-420, a one-part elastic, pigmented polyurethane coating with a tensile strength of approx. 5 MPa and an elongation at break of approx. 200%, from Sika) after a curing time of 24 hours in normal climate with a layer of 0.15 mm of each transparent one-part polyurethane system. After a curing time of 24 hours in normal climate, a first strip peel adhesion test was performed ("1d NC").
  • each test sample was immersed in water at room temperature for 24 hours, followed by taking it out of the water, wiping it with a cloth and doing a second strip peel adhesion test right after ("1d water”).
  • the strip peel adhesion test is performed by cutting a strip of 50 mm length and 10 mm width with a doctor knife into the surface of the film, in such a way, that the transparent top coat is cut down to the pigmented layer with no or only minimal cutting into the pigmented layer.
  • the transparent top coat is cut away from the pigmented layer at one end of the strip, and the rest of the strip is tried to peel off the pigmented coating by pulling the loose part of the strip upwards, with judging the force needed to peel it off.
  • the strip peel adhesion was rated “excellent”, if it was not possible to peel the top coat from the pigmented coat. It was rated “good”, if the top coat could only be peeled off the pigmented coat with considerable resistance, “some”, if there was some resistance, and “poor”, if the top coat could be peeled from the pigmented coat with only minimal or no force. "Poor adhesion” indicates that the coating is not beneficial for the outdoor use as top coat. The results are given in Table 2.
  • Table 2 Composition (in weight parts) and test results of the Compositions C1 to C9.
  • “(Ref.)” means “reference example”
  • “n.d.” means “not determined”
  • Table 3 Composition (in weight parts) of the Compositions C10 to C12.
  • compositions were tested as follows: The viscosity was measured as previously described, a first time after storing the moisture-tight container in normal climate for one day ("1d NC”), and again after storing the moisture-tight container in an oven at 40°C for 6 weeks (“6w 40°C”) The odour was judged by smelling with the nose from a distance of approximately 150 mm an amount of 50 g of the composition, which was spread out to a layer thickness of approximately 1 mm. "Slight” indicates a slight amine-like odour, “intense” indicates a strong, sharp odour . Cure speed was determined at normal climate (“BK drying time at NC”) and also at 5°C/30% relative humidity (“BK drying at 5°C/30%rh”) using a Beck-Koller drying time recorder according to ASTM D5895.
  • the tensile strength and the elongation at break were determined as previously described.
  • a glass plate coated with a cured film of 0.1 mm thickness was made.
  • the cured films of all the coatings were homogenous, non-tacky and bubble-free. Such films are indicated as “clear” in Table 4.
  • "Opaque” means that the film was not fully transparent.
  • the transparency was determined by measuring the absorption of the coated glass plate in a spectrophotometer (SF600 CT-plus, from Datacolor) with D65 artificial light, wherein "0" indicates full transparency and "100” indicates full absorption, which means full intransparency. Values below “20” indicate high transparency, values below "10” indicate very high transparency.
  • the heat age at 80°C and the hydrolysis at 70°C/100%rh were determined with a cured film as described for the determination of the tensile strength, which was additionally stored for 4 weeks in an oven at 80°C or for 4 weeks in a chamber with 70°C at 100% relative humidity, respectively, follwed by 24 hours in normal climate, before the tensile strength and the elongation at break were determined as described before.
  • a loss of strength and/or a loss of elongation in comparison to the original values without heat age or hydrolysis indicates limited resistance to heat or hydrolysis.
  • An increase of strength without a loss of elongation is a typical phenomena when some of the TOU evaporates from the film in the heat.
  • the UV resistance was determined with the same QUV accelerated wheathering setting and judgement as described before, but with two layer samples:
  • the aluminium panels were first coated with 1.29 kg/m 2 (1 mm) of Sikafloor®-420 (one- part elastic, pigmented polyurethane coating, from Sika), and - after a curing time of 24 h at normal climate - with 0.3 kg/m 2 of each composition as top coat.
  • the so- prepared samples were tested after 24 h curing at normal climate, followed by 72 h curing in an oven at 60°C, followed by another 24 h curing at normal climate.
  • the interlayer adhesion was determined in the same way as described before.
  • a strip peel adhesion test was made after 1 d, 7 d and 28 d curing at normal climate. Further strip peel adhesion tests were made with a film after 28 d curing at normal climate, followed by 1 d, 7d and 28 d water immersion at 23°C. Further strip peel adhesion tests were made with a film after 28 d curing at normal climate followed by 5 d, 14 d and 28 d water immersion at 70°C. The results are given in Table 4.
  • Sikafloor® 416 from Sika
  • Sikafloor® 418W from Sika
  • Sika a commercial water-based transparent one-part polyurethane top coat with a solids content of 42 weight-%
  • a balcony floor of 12 m 2 over grinded concrete was provided with an inventive floor covering system.
  • the ambient conditions were 18 to 22°C and 40 to 50% relative humidity.
  • a layer of Sikafloor®-407 (from Sika) was first applied as primer in an amount of 0.3 kg/m 2 onto the grinded concrete with a paint roller.
  • a layer of Sikafloor®-420 RAL 7035 (light grey) was applied as pigmented coating in an amount of 1 kg/m 2 onto the primer with a paint roller, followed by sprinkling colored flakes in an amount of 50 g/m 2 over the still wet surface.
  • a layer of the composition C10 was applied as transparent elastic top coat in an amount of 0.15 kg/m 2 with a paint roller onto the pigmented coating including the flakes.
  • the top coat was easy to roll onto the pigmented coating including the flakes to give a smooth, transparent surface.
  • the composition C10 cured to a smooth, transparent elastic layer without bubbles or pinholes and a non-tacky surface.
  • the obtained floor had a grey pattern with a highly aesthetical look and a high scratch and abrasion resistance at high durability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition de polyuréthane durcissant à l'humidité en une partie, comprenant – au moins un polymère à fonction isocyanate ayant une teneur en NCO dans la plage de 5 à 10 % en poids par rapport au polymère total, obtenu à partir de la réaction d'au moins un diisocyanate aliphatique avec au moins un polyol choisi dans le groupe constitué de poly(oxy -1,4-butylène) diols, de diols de polycarbonate aliphatique à base d'un diol linéaire et de diols de polyester à base d'acide gras dimère amorphe, éventuellement en combinaison avec au moins un allongeur de chaîne qui est un diol avec deux groupes hydroxyle primaires et un poids moléculaire dans la plage de 60 à 150 g/mol, et – au moins une aldimine de la formule (I). La composition de l'invention permet d'obtenir des revêtements élastiques présentant de bonnes propriétés d'application à haute teneur en solides, une résistance élevée et une durabilité élevée à une élasticité élevée et une stabilité élevée contre les UV et l'hydrolyse, appropriés pour l'utilisation en tant que revêtement supérieur transparent sur des sols de polyuréthane élastiques, qui sont exposés à des conditions environnementales difficiles.
PCT/EP2021/078816 2020-10-19 2021-10-18 Revêtement supérieur en polyuréthane transparent à haute performance WO2022084253A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115418162A (zh) * 2022-09-30 2022-12-02 佛山市科顺建筑材料有限公司 双组份聚氨酯防水涂料组合物及其制备方法、应用该双组份聚氨酯防水涂料组合物的结构
WO2024078045A1 (fr) * 2022-10-13 2024-04-18 立邦涂料（中国）有限公司 Dispersion de polyuréthane à base d'eau pour revêtement d'automobile et procédé de préparation s'y rapportant et son utilisation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4853454A (en) * 1986-07-23 1989-08-01 Basf Aktiengesellschaft Preparation of storage-stable, moisture-cured, single-component polyurethane systems and their uses
US8178167B2 (en) 2006-06-30 2012-05-15 Sika Technology Ag VOC-free or VOC-poor polyurethane coating
US20120220736A1 (en) * 2007-07-16 2012-08-30 Sika Technology Ag Aldimines and compositions comprising aldimine
US9752054B2 (en) 2013-01-22 2017-09-05 Sika Technology Ag Liquid-applied waterproofing membrane for roofs comprising a trialdimine
US9879154B2 (en) * 2013-01-22 2018-01-30 Sika Technology Ag Liquid-applied waterproofing membrane for roofs comprising two different aldimines

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4853454A (en) * 1986-07-23 1989-08-01 Basf Aktiengesellschaft Preparation of storage-stable, moisture-cured, single-component polyurethane systems and their uses
US8178167B2 (en) 2006-06-30 2012-05-15 Sika Technology Ag VOC-free or VOC-poor polyurethane coating
US20120220736A1 (en) * 2007-07-16 2012-08-30 Sika Technology Ag Aldimines and compositions comprising aldimine
US9752054B2 (en) 2013-01-22 2017-09-05 Sika Technology Ag Liquid-applied waterproofing membrane for roofs comprising a trialdimine
US9879154B2 (en) * 2013-01-22 2018-01-30 Sika Technology Ag Liquid-applied waterproofing membrane for roofs comprising two different aldimines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115418162A (zh) * 2022-09-30 2022-12-02 佛山市科顺建筑材料有限公司 双组份聚氨酯防水涂料组合物及其制备方法、应用该双组份聚氨酯防水涂料组合物的结构
WO2024078045A1 (fr) * 2022-10-13 2024-04-18 立邦涂料（中国）有限公司 Dispersion de polyuréthane à base d'eau pour revêtement d'automobile et procédé de préparation s'y rapportant et son utilisation

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