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WO2025093409A1 - Composition de revêtement à deux composants - Google Patents

Composition de revêtement à deux composants Download PDF

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Publication number
WO2025093409A1
WO2025093409A1 PCT/EP2024/080032 EP2024080032W WO2025093409A1 WO 2025093409 A1 WO2025093409 A1 WO 2025093409A1 EP 2024080032 W EP2024080032 W EP 2024080032W WO 2025093409 A1 WO2025093409 A1 WO 2025093409A1
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Prior art keywords
component
coating composition
polyisocyanate
component coating
composition according
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PCT/EP2024/080032
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Inventor
Chintankumar Jayantilal PATEL
Manfred Dargatz
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BASF SE
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BASF SE
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Classifications

    • 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
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
    • C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
    • C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates

Definitions

  • the present invention relates to a two-component coating composition
  • a two-component coating composition comprising a polyisocyanate composition as component (I) and an aqueous dispersion of a hydroxy-functional polymer P as component (ii), a method for production thereof and use thereof.
  • emulsion polymers are used as binders for coatings of substrates, one of the important requirements of such coatings is that they show a fast property development, i.e., fast hardness development or fast drying.
  • Polyisocyanate components are added to the composition containing aqueous polymer dispersions, as crosslinking agents, and are widely described in the literature. For the ease of incorporation conventional polyisocyanates are blended with solvents.
  • Hydrophilic modified polyisocyanates are often used as crosslinking agents. Such modifications can be advantageously distributed in water-based paints. It has been found that coatings produced with this binder systems have a better gloss than acrylate dispersions cross-linked with unmodified hydrophobic polyisocyanates. On the other hand, coatings with unmodified hydrophobic polyisocyanates show good performance properties but pose challenge for achieving combination of better gloss and satisfactory drying times.
  • EP 0 697 424 teaches the mixture of hydrophilic modified polyisocyanates with ethylencarbonate or y-butyrolactone as crosslinking agents for aqueous polymer dispersions.
  • the acrylic dispersion cross-linked in this way left much to be desired in terms of drying times at better gloss.
  • WO 9403516 describes mixtures of polyols in water or a water/solvent mixture and polyisocyanates.
  • the underlying problem was to provide further two-component coating compositions, which provide faster drying and/or hardness development compared to hitherto systems, still having a sufficient gloss.
  • a two-component coating composition comprising component (I) which is a composition comprising la) at least one polyisocyanate and ib) at least one y-lactone, which carries 1 or 2 radicals selected from the group consisting of Ci-Ce alkyl, Ci-Ce- alkoxy and methylcarboxylat-Ci-C4 alkyl and component (ii) comprising at least one aqueous dispersion of a hydroxy-functional polymer P.
  • component (I) which is a composition comprising la) at least one polyisocyanate and ib) at least one y-lactone, which carries 1 or 2 radicals selected from the group consisting of Ci-Ce alkyl, Ci-Ce- alkoxy and methylcarboxylat-Ci-C4 alkyl and component (ii) comprising at least one aqueous dispersion of a hydroxy-functional polymer P.
  • the present invention further relates to coated substrates which are obtainable using such a two-component coating composition.
  • the solids content of the aqueous dispersion in wt% is mentioned, it is based on the weight of the aqueous dispersion.
  • (meth)acrylic acid compounds or “(meth)acrylate” compounds is intended generally to comprise not only the corresponding acrylic acid compounds but also the corresponding methacrylic acid compounds.
  • the two-component coating compositions comprise a polyisocyanate composition as first component (I) and an aqueous dispersion of a hydroxy-functional polymer P as second component (ii).
  • component (I) comprises a substituted y-lactone.
  • Cyclic esters of 4-hydroxy carboxylic acids R-CH(OH)-(CH2)2-COOH
  • y-lactones gamma-lactones
  • y-lactones are substituted, preferably are substituted with one radical selected from Ci-Ce alkyl, Ci-Ce-alkoxy and methylcarboxylat-Ci-C4 alkyl, preferably a C1-C4 alkyl radical, especially methyl.
  • Preferred are y-valerolactone and o-methyl-y-butyrolactone and especially preferred is y-valerolactone.
  • y-lactones are biobased as determined using ASTM D6866-12.
  • biobased indicates that the carbon is of biological origin and comes from a biomaterial/renewable resource.
  • the content in bio-carbon and the content in biomaterial are expressions that indicate the same value.
  • a material of renewable origin or biomaterial is an organic material wherein the carbon comes from the CO2 fixed recently (on a human scale) by photosynthesis from the atmosphere.
  • a biomaterial Carbon of 100% natural origin
  • the isotopic 14 C is formed in the atmosphere and is then integrated via photosynthesis, according to a time scale of a few tens of years at most.
  • the half-life of the 14 C is 5,730 years.
  • the materials coming from photosynthesis namely plants in general, necessarily have a maximum content in isotope 14 C.
  • the determination of the content of biomaterial or of bio-carbon can be carried out in accordance with the standards ASTM D 6866-12.
  • the y-lactones is derived from biomass, more preferably from starch or sugars, most preferably from glucose, fructose, or cellulose.
  • the preparation of the y-lac- tones from biomass is known, for example, from Shanta Dutta, Iris K.M. Yu, Daniel C.W. Tsang, Yun Hau Ng, Yong Sik Ok, James Sherwood, James H. Clark, ''Green synthesis of gamma-verolactone through hydrogenation of bio- mass-derived levulinic acid using non-noble metal catalysts”, Chemical Engineering Journal 372 (2019), 992-1006.
  • the polyisocyanate component comprises at least one polyisocyanate as component ia).
  • At least one polyisocyanate means one polyisocyanate or a mixture of two or more polyisocyanates with different compositions, preference being given to one polyisocyanate.
  • one polyisocyanate likewise embraces a mixture of polyisocyanates which differ merely in their chain length and/or in the arrangement of the monomers within the polymer chain.
  • the polyisocyanate contains at the most 0.01 mol equivalent moieties selected from anionic groups and/or polyalkylene oxide blocks per mol equivalent of isocyanate group.
  • anionic group is intended generally to comprise not only the anion of an acid group but also the corresponding acid group, for example a sulfo group.
  • Groups convertible into anionic groups are preferably converted into anionic groups during dispersing of it in water.
  • inorganic and/or organic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium bicarbonate, ammonia or primary, secondary or in particular tertiary amines, eg. triethylamine or dimethylaminopropanol, may be used.
  • Polyalkylene oxide is synonym to poylalkylene glycol. "Polyalkylene oxide block” is a chain having from 2 to 80 alkylene oxide units. Alkylene oxide units may be ethylene ether groups or mixture with other alkylene oxide units, eg. propylene ether groups.
  • the polyisocyanate is fully unmodified. This means it does not contain any hydrophilic moieties.
  • the at least one polyisocyanate can be prepared by polymerization of monomeric aromatic, aliphatic and/or cycloaliphatic isocyanates, preferably of aliphatic and/or cycloaliphatic (in this text referred to as (cyclo)ali phatic for short) isocyanates and particularly preferably of aliphatic isocyanates.
  • Aromatic isocyanates are isocyanates which comprise at least one aromatic ring system, i.e., either purely aromatic compounds or araliphatic compounds.
  • the former are isocyanates in which the isocyanato groups are bound directly to aromatic ring systems, while in the case of the latter the isocyanato groups are bound to alkylene groups but the compounds also comprise aromatic ring systems, as is the case, for example, in a,a,a‘,a‘-tetramethylxylylene 1,3- diisocyanate (TMXDI).
  • Cycloaliphatic isocyanates are ones which comprise at least one cycloaliphatic ring system.
  • Aliphatic isocyanates are ones which comprise exclusively linear or branched carbon chains, i.e., acyclic compounds.
  • the monomeric aromatic, aliphatic and/or cycloaliphatic isocyanates can in each case be identical or different isocyanates.
  • the monomeric aromatic, aliphatic and/or cycloaliphatic isocyanates are preferably diisocyanates, which bear precisely two isocyanate groups.
  • isocyanates having an average of more than two isocyanate groups are also possible in principle.
  • suitable compounds of this type are triisocyanates such as triisocyanatononane, 2'-isocy anatoethy I 2, 6-diisocy a- natohexanoate, 2,4,6-triisocyanatotoluene, triphenylmethane triisocyanate or 2,4,4'-triisocyanato(diphenyl ether) or the mixtures of diisocyanates, triisocyanates and higher polyisocyanates.
  • the monomeric aromatic, aliphatic and/or cycloaliphatic isocyanates have no significant reaction products of the isocyanate groups with themselves.
  • the monomeric aromatic, aliphatic and/or cycloaliphatic isocyanates are preferably isocyanates having from 4 to 20 carbon atoms.
  • customary diisocyanates are aliphatic diisocyanates such as tetramethylene diisocyanate, pentamethylene 1 ,5-diisocyanate (PDI), hexamethylene diisocyanate (1,6-diisocyanatohexane) (HDI), octamethylene diisocyanate, decamethylene diisocyanate, dodecamethylene diisocyanate, tetradecamethylene diisocyanate, derivatives of lysine diisocyanate (e.g.
  • methyl or ethyl 2,6-diisocyanatohexanoate trimethylhexane diisocyanate or tetramethylhexane diisocyanate
  • cycloaliphatic diisocyanates such as 1 ,4-, 1 ,3- or 1 ,2-diisocyanatocyclohex- ane, 4,4'- or 2,4'-di(isocyanatocyclohexyl)methane, 1-isocyanato-3,3,5-trimethyl-5-(isocyanatomethyl)cyclohexane (isophorone diisocyanate or IPDI), 1,3- or 1 ,4-bis(isocyanatomethyl)cyclohexane or 2,4- or 2,6-diisocyanato-1 - methylcyclohexane and also 3- (or 4-), 8- (or 9-)bis(isocyanatomethyl)tricyclo[5.2.1.02.6]decane iso
  • hexamethylene 1,6-di isocyan ate pentamethylene 1 ,5-diisocyanate, 1 ,3-bis(isocy- anatomethyl)cyclohexane, isophorone diisocyanate and 4,4'- or 2,4'-di(isocyanatocyclohexyl)methane, with very particular preference being given to isophorone diisocyanate and hexamethylene 1 ,6-diisocyanate, in particular hexamethylene 1 ,6-diisocyanate.
  • Isophorone diisocyanate is usually present as a mixture, namely of the cis and trans isomers, generally in a ratio of from about 60:40 to 90:10 (w/w), preferably from 70:30 to 90:10.
  • Dicyclohexylmethane 4,4'-diisocyanate can likewise be present as a mixture of the various cis and trans isomers.
  • diisocyanates it is possible to use both diisocyanates which are obtained by phosgenation of the corresponding amines and also those which are prepared without the use of phosgene, i.e., by phosgene-free processes.
  • (cyclo)aliphatic diisocyanates e.g., hexamethylene 1 ,6-diisocyanate (HDI), isomeric aliphatic diisocyanates having 6 carbon atoms in the alkylene radical, 4,4'- or 2,4'-di(isocyanatocyclohexyl)methane and 1-isocyanato-3-isocy- anatomethyl-3,5,5-trimethylcyclohexane (isophorone diisocyanate or IPDI) can be prepared by reacting the (cyclo)ali- phatic diamines with, for example, urea and alcohols to form (cyclo)aliphatic biscarbamic esters and thermal dissociation of these into the corresponding diisocyanates and alcohols.
  • cyclo)aliphatic diisocyanates e.g., hexamethylene 1 ,6-diisocyanate (HDI)
  • the synthesis is usually carried out continuously in a circulatory process and optionally in the presence of N-unsubstituted carbamic esters, dialkyl carbonates and other by-products recirculated from the reaction process.
  • Diisocyanates obtained in this way generally have a very small or even unmeasurable proportion of chlorinated reaction products, which is advantageous, for example, in applications in the electronics industry, without being restricted thereto.
  • the isocyanates used can have a total content of hydrolyzable chlorine of less than 200 ppm, preferably less than 120 ppm, particularly preferably less than 80 ppm, very particularly preferably less than 50 ppm, in particular less than 15 ppm and especially less than 10 ppm. This can, for example, be measured according to the ASTM method D4663-98. However, it is of course also possible to use monomeric isocyanates having a higher chlorine content, for example up to 500 ppm.
  • the average NCO functionality of the at least one polyisocyanate is generally at least 1 .8 and can be up to 8, for example up to 6, preferably from 2 to 5 and particularly preferably from 2.4 to 4.
  • the at least one polyisocyanate is preferably selected from among the following compounds:
  • the isocyanatoisocyanurates generally have an NCO content of from 10 to 30% by weight, in particular from 15 to 25% by weight, and an average NCO functionality of from 2.6 to 8.
  • the polyisocyanates having isocyanurate groups can also contain smaller amounts of urethane and/or allophanate groups, preferably with a content of bound alcohol of less than 2% by weight based on the polyisocyanate.
  • Polyisocyanates having uretdione groups are frequently obtained in admixture with other polyisocyanates, in particular those mentioned under item 1).
  • Polyisocyanates having uretdione groups usually have NCO functionalities of from 2 to 3.
  • the diisocyanates can be reacted under reaction conditions under which both uretdione groups and also the other polyisocyanates are formed, or the uretdione groups are formed first and these are subsequently converted into the other polyisocyanates or the diisocyanates are firstly reacted to form the other polyisocyanates and these are subsequently converted into products comprising uretdione groups.
  • polyisocyanates having biuret groups generally have an NCO content of from 18 to 24% by weight and an average NCO functionality of from 2.8 to 6.
  • Polyisocyanates having biuret groups are frequently obtained in admixture with other polyisocyanates, in particular urea, and those mentioned under item 1 and 2.
  • These polyisocyanates having urethane and/or allophanate groups generally have an NCO content of from 12 to 24% by weight and an average NCO functionality of from 2.0 to 4.5.
  • Such polyisocyanates having urethane and/or allophanate groups can be prepared in the absence of catalysts or preferably in the presence of catalysts, for example ammonium carboxylates or ammonium hydroxides or allophanatization catalysts, e.g., bismuth compounds, cobalt compounds, cesium compounds, Zn(ll) or Zr(IV) compounds, in each case in the presence of monohydric, dihydric, or polyhydric, preferably monohydric, alcohols.
  • catalysts for example ammonium carboxylates or ammonium hydroxides or allophanatization catalysts, e.g., bismuth compounds, cobalt compounds, cesium compounds, Zn(ll) or Zr(IV) compounds, in each case in the presence of monohydric, dihydric, or polyhydric, preferably monohydric, alcohols.
  • Polyisocyanates comprising iminooxadiazinedione groups are frequently obtained in admixture with other polyisocyanates, in particular mentioned under item 1 and 2.
  • the polyisocyanates 1)-9) described under the abovementioned items, preferably 1), 2), 3), 4) and 6), can, after they have been prepared, be converted into polyisocyanates having biuret groups or urethane/allophan- ate groups and aromatically, cycloaliphatically, or aliphatically bound, preferably (cyclo)aliphatically bound, isocyanate groups.
  • the formation of biuret groups is affected, for example, by addition of water or reaction with amines.
  • urethane and/or allophanate groups is affected by reaction with monohydric, dihydric, or polyhydric, preferably monohydric, alcohols, optionally in the presence of suitable catalysts.
  • polyisocyanates having biuret or urethane/allophanate groups generally have an NCO content of from 10 to 25% by weight and an average NCO functionality of from 3 to 8.
  • Polyisocyanates which comprise not only the groups described under 1 ) to 10) but also groups which are formally formed by addition of molecules having NCO-reactive groups and groups which are crosslinkable by means of UV or actinic radiation onto the isocyanate groups of the above molecules.
  • These molecules are, for example, hydroxyalkyl (meth)acrylates and other hydroxyvinyl compounds.
  • the diisocyanates or polyisocyanates described above can also be present at least partly in blocked form.
  • Examples of classes of compounds used for blocking are phenols, imidazoles, triazoles, pyrazoles, oximes, N- hydroxyimides, hydroxybenzoic esters, secondary amines, lactams, CH-acidic cyclic ketones, malonic esters, or alkyl acetoacetates.
  • the at least one polyisocyanate can be selected from the group consisting of polyisocyanurates and polyisocyanates comprising iminooxadiazinedione groups biurets, urethanes and allophanates, preferably from the group consisting of isocyanurates, isocyanates comprising iminooxadiazinedione groups, urethanes and allophanates, with particular preference being given to a polyisocyanate comprising iminooxadiazinedione groups and/or isocyanurate groups.
  • the at least one polyisocyanate is particularly preferably a polyisocyanate based on aliphatic and/or cycloaliphatic diisocyanates, very particularly preferably based on hexamethylene 1 ,6-diisocyanate, pentamethylene 1,6- diisocyanate and/or isophorone diisocyanate.
  • the at least one polyisocyanate being a mixture of polyisocyanates, very particularly preferably polyisocyanates based on hexamethylene 1 ,6-diisocyanate and polyisocyanates based on isophorone diisocyanate.
  • the at least one polyisocyanate is a mixture comprising low-viscosity polyisocyanates, preferably low-viscosity polyisocyanates comprising isocyanurate groups, having a viscosity of from 600 to 3500 mPa*s, in particular less than 1500 mPa*s, low-viscosity urethanes and/or allophanates having a viscosity of from 200 to 1600 mPa*s, in particular from 500 to 1500 mPa*s, and/or polyisocyanates comprising iminooxadiazinedione groups and having a viscosity of from 400 to 2000 mPa*s, in particular from 500 to 1500 mPa*s.
  • the at least one polyisocyanate can, for example, be prepared by methods known to those skilled in the art.
  • the process for preparing the at least one polyisocyanate can be carried out as described in WO 2008/68198, there in particular on page 20, line 21 to page 27, line 15, which is hereby incorporated by reference into the present patent application.
  • reaction can, for example, be stopped as described there on page 31, line 19 to page 31, line 31 and the workup can be carried out as described there on page 31, line 33 to page 32, line 40, which is in each case incorporated by reference into the present patent application.
  • reaction can, as an alternative, also be stopped as described in WO 2005/087828 on page 11, line 12 to page 12, line 5, which is hereby incorporated by reference into the present patent application.
  • thermally labile catalysts are used in the process for preparing the at least one polyisocyanate, it is also possible to stop the reaction by heating the reaction mixture to a temperature above at least 80°C, preferably at least 100°C, particularly preferably at least 120°C. The heating of the reaction mixture is necessary to separate off the unreacted isocyanate by distillation in the work-up is generally sufficient for this purpose.
  • Suitable deactivators are, for example, hydrogen chloride, phosphoric acid, organic phosphates such as dibutyl phosphate or diethyl hexyl phosphate, carbamates such as hydroxyalkyl carbamate or organic carboxylic acids.
  • Diisocyanates, triisocyanates and higher polyisocyanates can, for example, be obtained by phosgenation of corresponding aniline/formaldehyde condensates and can be polyphenyl polyisocyanates having methylene bridges.
  • the composition is obtained by assembling the constituent parts. For example, this is done by means of mixing devices, like mechanical stirrer.
  • Component (I) of the two-component coating composition is obtained by combining the polyisocyanate and the y- lactone. This can be done by just simple mixing of both components with mechanical stirrer.
  • the component (I) comprises 5 to 50 % by weight y-lactone based on the sum of polyisocyanate la) and y- lactone ib).
  • the y-lactones as a component of the 2K composition according to the invention, lead to advantageous properties of the surface coatings.
  • Well-known diluents are, for example but not limited to: methoxypropyl acetate, dipropylene glycol dimethyl ether, dipropyleneglycol mono methyl ether acetate, butyl glycol acetate, propylene carbonate, TME 1 ,1 ,2,2-tetramethoxyethane, dioxane, dioxolane, ethyl acetate, butyl acetate, ethylene glycol monoethyl or ethyl ether acetate, 1-methoxypropyl 2-acetate, 2-butanone, 4-methyl-2-pentanone, cyclohexane, toluene, propylene glycol diacetate, diethylene glycol dimethyl ether, diethylene glycol ethyl or butyl ether acetate, N-methylpyrrolidone, N-ethylpyrrolidone, N-methylcaprolactam and THF.
  • Common additives for polyisocyanates are silane additives and/or catalyst for formation of urethane.
  • Hydroxy-functional polymers P can be, for example, polyacrylate polyols, polyester polyols, polyether polyols, polyurethane polyols; polyurea polyols; polyester polyacrylate polyols; polyester polyurethane polyols; polyurethane polyacrylate polyols, polyurethane-modified alkyd resins; fatty acid-modified polyester polyurethane polyols, copolymers with allyl ethers, graft polymers from the abovementioned groups of materials having, for example, different glass transition temperatures, and also mixtures of the polymers mentioned.
  • the polymers dispersed in the polymer dispersion are particularly preferably polyacrylate polyols and polyesterols, especially a polyacrylate polyol.
  • Preferred OH numbers measured in accordance with DIN 53240-2 (potentiometric), are 40-350 mg KOH/g of solid resin for polyesters, preferably 80-180 mg KOH/g of solid resin, and 15-250 mg KOH/g of solid resin for polyacrylate alcohols, preferably from 80 to 160 mg KOH/g.
  • the polymers dispersed in the polymer dispersion can have an acid number in accordance with DIN EN ISO 3682 (potentiometric) up to 200 mg KOH/g, preferably up to 150 and particularly preferably up to 100 mg KOH/g.
  • Hydroxy-functional polymers P are, for example, polyester polyols of the kind obtainable by condensing polycarboxylic acids, more particularly dicarboxylic acids, with polyols, more particularly diols.
  • polyester polyols of the kind obtainable by condensing polycarboxylic acids, more particularly dicarboxylic acids, with polyols, more particularly diols.
  • polyols more particularly diols.
  • the polyester polyol has a functionality appropriate for the polymerization use is also made in part of triols, tetrols, etc., and of tribasic acids, etc.
  • Polyester polyols are known for example from Ullmann's Enzyklopadie der ischen Chemie, 4th edition, volume 19, pages 62 to 65. It is preferred to use polyester polyols obtained by reacting dihydric alcohols with dibasic carboxylic acids. In place of the free polycarboxylic acids it is also possible to use the corresponding polycarboxylic anhydrides or corresponding polycarboxylic esters of lower alcohols or mixtures thereof to prepare the polyester polyols.
  • the polycarboxylic acids may be aliphatic, cycloaliphatic, aromatic, or heterocyclic and may optionally be substituted, by halogen atoms, for example, and/or unsaturated.
  • polyacrylate polyol covers copolymers of hydroxyl functional acrylic and/or methacrylic monomers in combination with other comonomers.
  • Polyacrylate polyols preferably have a molecular weight Mn of at least 500 g/mol, particularly preferably at least 1200 g/mol.
  • the molecular weight Mn can in principle have no upper limit, and is preferably up to 50 000 g/mol, particularly preferably up to 20 000 g/mol, very particularly preferably up to 10 000 g/mol and in particular up to 5000 g/mol.
  • the number-average molecular weights are determined by gel permeation chromatography, which is familiar to the skilled person, using suitable calibration compounds.
  • the polyacrylate polyol may be a secondary dispersion, i.e., polymer produced by solution polymerization, which is then dispersed in water.
  • the preparation of the polymers dispersed in the polymer dispersion is preferably carried out by means of emulsion polymerization.
  • Hydroxy-functional monomers can be concomitantly used in the copolymerization in such amounts that the abovementioned hydroxyl numbers of the copolymers result, generally corresponding to a hydroxy group content of the copolymers of from 0.5 to 8% by weight, preferably from 1 to 5% by weight.
  • the hydroxy functional polymer P is prepared by polymerization of at least one hydroxy-functional (meth)acrylate Ma) and at least one Monomer Mb) selected from the group consisting of alkyl (meth)acrylates, vinylaromatics, a,p-unsaturated carboxylic acids, and other monomers.
  • Preferred hydroxyl numbers of the at least one hydroxy-functional polymer (solid), are 15-250 mg KOH/g, preferably 40-120 mg KOH/g polymer.
  • alkyl (meth)acrylates include C1-C20 alkyl (meth)acrylates, vinylaromatics are those having up to 20 carbon atoms, a,p-unsaturated carboxylic acids also include their anhydrides, and other monomers are, for example, vinyl esters of carboxylic acids containing up to 20 carbon atoms, ethylenically unsaturated nitriles, vinyl ethers of alcohols containing 1 to 10 carbon atoms, and, less preferably, aliphatic hydrocarbons having 2 to 8 carbon atoms and 1 or 2 double bonds.
  • alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n- butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, n-pentyl (meth)acrylate, isopentyl (meth)acrylate, 2-methylbutyl (meth)acrylate, amyl (meth)acrylate, n-hexyl (meth)acrylate, 2-ethylbutyl (meth)acrylate, pentyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2- propylheptyl (meth)acrylate, n-decyl (meth)acrylate, undecyl (meth)acrylate
  • Preferred alkyl (meth)acrylates are those having a C1-C10 alkyl radical, particular preference being given to methyl methacrylate, methyl acrylate, ethyl acrylate, n-butyl acrylate, n-butyl methacrylate, n-hexyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate and/or 3-propylheptyl acrylate.
  • mixtures of the alkyl (meth)acrylates are also suitable.
  • Vinyl esters of carboxylic acids having from 1 to 20 carbon atoms are, for example, vinyl laurate, vinyl stearate, vinyl propionate and vinyl acetate.
  • a, p-unsaturated carboxylic acids and anhydrides thereof can be, for example, acrylic acid, methacrylic acid, fumaric acid, cratonic acid, itaconic acid, maleic acid or maleic anhydride, preferably acrylic acid.
  • hydroxyl (meth)acrylates mention may be made of monoesters of a,p-unsaturated acrylic acid and/or methacrylic acid (in this text referred to as "(meth)acrylic acid” for short), with diols or polyols which preferably have from 2 to 20 carbon atoms and at least two hydroxy groups, e.g.
  • ethylene glycol diethylene glycol, triethylene glycol, 1 ,2- propylene glycol, 1 ,3-propylene glycol, 1 ,1-dimethyl-1 ,2-ethanediol, dipropylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, tripropylene glycol, 1,4-butanediol, 1 ,5-pentanediol, neopentyl glycol, the hydroxypivalic ester of neopentyl glycol, 2-ethyl-1,3-propanediol, 2-methyl-1 ,3-propanediol, 2-butyl-2-ethyl-1 ,3- propanediol, 1 ,6-hexanediol, 2-methyl-1 ,5-pentanediol, 2-ethyl-1 ,4-butanediol, 2-ethyl-1 ,3-
  • 2-hydroxyethyl acrylate Preference is given to 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2- or 3-hydroxypropyl acrylate, 1 ,4- butanediol monoacrylate or 3-(acryloyloxy)-2-hydroxypropyl acrylate and particular preference is given to 2- hydroxyethyl acrylate and/or 2-hydroxyethyl methacrylate.
  • vinylaromatic compounds are, for example, vinyltoluene, o-butylstyrene, o-methylstyrene, 4— n— butylstyrene, 4-n-decylstyrene and preferably styrene.
  • nitriles are acrylonitrile and methacrylonitrile.
  • Suitable vinyl ethers are, for example, vinyl methyl ether, vinyl isobutyl ether, vinyl hexyl ether and vinyl octyl ether.
  • nonaromatic hydrocarbons having from 2 to 8 carbon atoms and one or two olefinic double bonds
  • N-vinylformamide, N-vinylpyrrolidone and N-vinylcaprolactam also ethylenically unsaturated acids, in particular carboxylic acids, acid anhydrides or acid amides, and also vinylimidazole.
  • Comonomers having epoxide groups e.g., glycidyl acrylate or methacrylate, or monomers such as N-methoxymethylacrylamide or N- methoxymethacrylamide can also be concomitantly used in small amounts.
  • esters of acrylic acid or of methacrylic acid having from 1 to 18, preferably from 1 to 8, carbon atoms in the alcohol radical, e.g., methyl acrylate, ethyl acrylate, isopropyl acrylate, n-propyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, n-stearyl acrylate, the methacrylates corresponding to these acrylates, styrene, alkylsubstituted styrenes, acrylonitrile, methacrylonitrile, vinyl acetate or vinyl stearate or any mixtures of such monomers.
  • the hydroxy-functional monomers are used in a mixture with other polymerizable monomers, preferably radically polymerizable monomers, preferably those which consist to an extent of more than 50 wt% of C1-C20 alkyl (meth)acrylate, preferably Ci to C4 alkyl (meth)acrylate, (meth)acrylic acid, vinylaromatics having up to 20 carbon atoms, vinyl esters of carboxylic acids containing up to 20 carbon atoms, vinyl halides, nonaromatic hydrocarbons having 4 to 8 carbon atoms and 1 or 2 double bonds, unsaturated nitriles, and mixtures thereof.
  • other polymerizable monomers preferably radically polymerizable monomers, preferably those which consist to an extent of more than 50 wt% of C1-C20 alkyl (meth)acrylate, preferably Ci to C4 alkyl (meth)acrylate
  • (meth)acrylic acid vinylaromatics having up to 20 carbon atoms, vinyl est
  • Particularly preferred polymers are those which in addition to the monomers which carry hydroxyl groups consist to an extent of more than 60 wt% of C1-C10 alkyl (meth)acrylates, styrene, and derivatives thereof, or mixtures of these, based on the total of monomers.
  • the copolymerization of the at least one hydroxy-functional poly(meth)acrylate is a radically initiated aqueous emulsion polymerization.
  • the implementation of free-radical initiated aqueous emulsion polymerizations has been the subject of many prior descriptions and is therefore sufficiently well-known to the skilled person [in this regard, see Emulsion Polymerization in Encyclopedia of Polymer Science and Engineering, vol. 8, pages 659 ff. (1987); D.C. Blackley, in High Polymer Latices, vol. 1, pages 35 ff. (1966); H. Warson, The Applications of Synthetic Resin Emulsions, chapter 5, pages 246 ff. (1972); D.
  • the usual format for the radically initiated aqueous emulsion polymerization is that the monomers are dispersed in the aqueous medium, generally with accompaniment of dispersing assistants, such as emulsifiers and/or protective colloids, and are polymerized by means of at least one water-soluble radical polymerization initiator.
  • dispersing assistants such as emulsifiers and/or protective colloids
  • the residual levels of unreacted monomers are frequently lowered by means of chemical and/or physical methods that are likewise known to the skilled person [see, for example, EP-A 771328, DE-A 19624299, DE-A 19621027, DE-A 19741184, DE-A 19741187, DE-A 19805122, DE-A 19828183, DE-A 19839199, and DE-A 19840586 and 19847115], the polymer solids content is adjusted to a desired figure by dilution or concentration, or further customary adjuvants, such as foam- or viscosity-modifying additives, for example, are added to the aqueous polymer dispersion.
  • customary adjuvants such as foam- or viscosity-modifying additives, for example
  • the radically initiated aqueous emulsion polymerization may take place in a multistage polymerization process.
  • a multistage polymerization process refers to the sequential polymerization of two or more separate monomer mixtures in two or more separate operations.
  • the radically initiated aqueous emulsion polymerization is carried out generally in the presence of 0.1 to 5 wt%, preferably 0.1 to 4 wt%, and more particularly 0.1 to 3 wt%, based in each case on the total monomer amount, of a radical polymerization initiator (radical initiator).
  • Radical initiators contemplated include all those capable of initiating a radical aqueous emulsion polymerization. These may in principle be both peroxides and azo compounds. It will be appreciated that redox initiator systems are also contemplated.
  • inorganic peroxides such as hydrogen peroxide or peroxodisulfates, such as the mono- or di-alkali metal or ammonium salts of peroxodisulfuric acid, such as its mono- and di-sodium, -potassium, or ammonium salts, for example, or organic peroxides, such as alkyl hydroperoxides, examples being tert-butyl, p-menthyl, or cumyl hydroperoxide, and also dialkyl or diaryl peroxides, such as di-tert-butyl peroxide or dicumyl peroxide.
  • inorganic peroxides such as hydrogen peroxide or peroxodisulfates, such as the mono- or di-alkali metal or ammonium salts of peroxodisulfuric acid, such as its mono- and di-sodium, -potassium, or ammonium salts
  • organic peroxides such as alkyl hydroperoxide
  • azo compound use is made substantially of 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(amidinopropyl) dihydrochloride (Al BA, corresponding to V-50 from Wako Chemicals).
  • Al BA 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(amidinopropyl) dihydrochloride
  • Oxidizing agents contemplated for redox initiator systems are essentially the peroxides identified above.
  • sulfur compounds with a low oxidation state such as alkali metal sulfites, as for example potassium and/or sodium sulfite, alkali metal hydrogensulfites, as for example potassium and/or sodium hydrogensulfite, alkali metabisulfites, as for example potassium and/or sodium metabisulfite, formaldehyde- sulfoxyl ates, as for example potassium and/or sodium formaldehyde-sulfoxylate, alkali metal salts, especially potassium salts and/or sodium salts aliphatic sulfinic acids, and alkali metal hydrogensulfides, such as potassium and/or sodium hydrogensulfide, for example, salts of polyvalent metals, such as iron(ll) sulfate, iron(ll) ammonium sulfate, iron(ll) phosphate, enediols, such as dihydroxymaleic acid, benzoin and/or ascorbic acid, and also
  • Initiation of the polymerization reaction means the start of the polymerization reaction of the monomers present in the polymerization vessel, after radical formation by the radical initiator.
  • This initiation of the polymerization reaction may be accomplished by adding radical initiator to the aqueous polymerization mixture in the polymerization vessel under polymerization conditions.
  • Another possibility, however, is to add a portion or the entirety of the radical initiator to the aqueous polymerization mixture, comprising the initially introduced monomers, in the polymerization vessel, under conditions not apt to trigger a polymerization reaction - at low temperature, for example - and thereafter to bring about polymerization conditions in the aqueous polymerization mixture.
  • Polymerization conditions here are, generally, those temperatures and pressures at which the radically initiated aqueous emulsion polymerization proceeds with sufficient polymerization rate. They are dependent in particular on the radical initiator used.
  • the nature and amount of the radical initiator, the polymerization temperature, and the polymerization pressure are selected such that the radical initiator has a half-life ⁇ 3 hours and especially advantageously ⁇ 1 hour and at the same time there are always sufficient initiating radicals available to initiate and maintain the polymerization reaction.
  • Reaction temperatures contemplated for the radically initiated aqueous emulsion polymerization span the whole range from 0 to 170°C. Temperatures employed here are generally from 50 to 120°C, preferably 60 to 110°C, and especially preferably 60 to 100°C.
  • the radically initiated aqueous emulsion polymerization may be carried out at a pressure less than, equal to, or greater than 1 atm [1.013 bar (absolute), atmospheric pressure], and so the polymerization temperature may exceed 100°C and may be up to 170°C. In the presence of monomers having a low boiling point, the emulsion polymerization is carried out preferably under increased pressure.
  • the pressure may take on values of 1.2, 1.5, 2, 5, 10, or 15 bar (absolute) or even higher. If the emulsion polymerization is carried out under subatmospheric pressure, pressures of 950 mbar, frequently of 900 mbar and often 850 mbar (absolute), are set.
  • the radical aqueous emulsion polymerization is carried out advantageously at 1 atm in the absence of oxygen, more particularly under inert gas atmosphere, such as under nitrogen or argon, for example.
  • the entirety of the radical initiator may be included in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated. Another possibility, however, is to include optionally only a portion of the radical initiator in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated, and then to add the entirety or any remainder during the radically initiated emulsion polymerization, under polymerization conditions, at the rate of its consumption, continuously or discontinuously. In a preferred embodiment, the entirety of the radical initiator is included in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated.
  • the total amount of radical initiators is > 0.05 and ⁇ 5 wt%, preferably > 0.1 and ⁇ 3 wt%, and more preferably > 0.1 and ⁇ 1.5 wt%, based in each case on the total monomer amount.
  • aliphatic and/or araliphatic halogen compounds such as, for example, n-butyl chloride, n-butyl bromide, n-butyl iodide, methylene chloride, ethylene dichloride, chloroform, bromoform, bromotrichloromethane, dibromodichloromethane, carbon tetrachloride, carbon tetrabromide, benzyl chloride, benzyl bromide, organic thio compounds, such as primary, secondary, or tertiary aliphatic thiols, such as, for example, ethanethiol, n-propanethiol, 2-propanethiol, n-butanethiol, 2-butanethiol, 2-methyl-2-propanethiol,
  • the entirety of the chain transfer agent may be included in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated. Another possibility, however, is to include optionally only a portion of the chain transfer agent in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated, and then to add the entirety or any remainder during the radically initiated emulsion polymerization, under polymerization conditions, as and when required, continuously or discontinuously. It is essential, however, that the nature and the amounts of the chain transfer agents are selected such that the stated weight-average molecular weights are obtained.
  • the amount of chain transfer agent is 0 to 20 wt%, preferably 0.05 to 10 wt%, and more preferably 0.1 to 2 wt%, based in each case on the total monomer amount.
  • the emulsion polymerization may optionally also be carried out in the presence of dispersing assistants, which keep both the monomer droplets and polymer particles in dispersion in the aqueous phase and so ensure the stability of the aqueous dispersions produced of the dispersion polymers.
  • dispersing assistants include emulsifiers as well as the protective colloids that are customarily used in the implementation of radical aqueous emulsion polymerizations.
  • Suitable protective colloids are polyvinyl alcohols, cellulose derivatives, or copolymers comprising vinylpyrrolidone.
  • a comprehensive description of further suitable protective colloids is found in Houben-Weyl, Methoden der organischen Chemie, volume XIV/1, Makromolekulare Stoffe [Macromolecular compounds], pages 411 to 420, Georg-Thieme-Verlag, Stuttgart, 1961 . It will be appreciated that mixtures of emulsifiers and/or protective colloids can also be used.
  • dispersing assistants it is preferred to use exclusively emulsifiers, whose relative molecular weights, in contrast to the protective colloids, are customarily below 1000 g/mol.
  • anionic emulsifiers are compatible with one another and with nonionic emulsifiers.
  • anionic and cationic emulsifiers are usually not compatible with one another.
  • Customary emulsifiers are, for example, ethoxylated mono-, di-, and trialkylphenols (EC degree: 3 to 50, alkyl radical: C4 to C12), ethoxylated fatty alcohols (EC degree: 3 to 50; alkyl radical: C8 to C36), and alkali metal salts and ammonium salts of alkyl sulfates (alkyl radical: C8 to C12), of sulfuric monoesters with ethoxylated alkanols (EC degree: 4 to 30, alkyl radical: C12 to C18) and with ethoxylated alkylphenols (EC degree: 3 to 50, alkyl radical: C4 to C12), of alkylsulfonic acids (alkyl radical: C12 to C18), and of alkylarylsulfonic acids (alkyl radical: C9 to C18).
  • alkyl radical: C4 to C12 alkyl radical: C4 to C12
  • dispersing assistants are used in accordance with the invention, use is made advantageously of anionic and/or nonionic, and especially advantageously of anionic, surfactants.
  • emulsifiers used are those which are incorporated into the polymer in the course of the radical emulsion polymerization. These are generally compounds which carry at least one radically polymerizable group, preferably selected from the group consisting of allyl, acrylate, methacrylate, and vinyl ether, and at least one emulsifying group, preferably selected from the group indicated above.
  • emulsifiers are, for example, incorporable emulsifiers with the brand names Bisomer® MPEG 350 MA from Laporte, Hitenol® BC-20 (APEO), Hitenol® BC-2020, Hitenol® KH-10 or Noigen® RN-50 (APEO) from Dai-lchi Kogyo Seiyaku Co., Ltd., Maxemul® 6106, Maxemul® 6112, Maxemul® 5010, Maxemul® 5011 from Croda, Sipomer® PAM 100, Sipomer® PAM 200, Sipomer® PAM 300, Sipomer® PAM 4000, Sipomer® PAM 5000 from Rhodia, Adeka® Reasoap® PP-70, Adeka® Reasoap® NE-10, Adeka® Reasoap® NE-20, Adeka® Reasoap® NE-30, Adeka® Reasoap® NE-40, Adeka® Re
  • the entirety of the optionally employed dispersing assistant may be included in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated. Another possibility, however, is to include optionally only a portion of the dispersing assistant in the initial charge in the aqueous reaction medium before the polymerization reaction is initiated, and then to add the entirety or any remainder during the radically initiated emulsion polymerization, under polymerization conditions, as and when required, continuously or discontinuously. Optionally, a portion ( ⁇ 50 wt%) of the dispersing assistants is included in the initial reaction vessel charge, and the remaining amounts (> 50 wt%) are metered in continuously.
  • the radically initiated aqueous emulsion polymerization may advantageously also be carried out in the presence of a polymer seed, as for example in the presence of 0.01 to 10 wt%, frequently of 0.05 to 7.0 wt%, and often of 0.1 to 4.0 wt% of a polymer seed, based in each case on the total monomer amount.
  • a polymer seed is employed in particular when the particle size of the polymer particles to be prepared by means of a radically initiated aqueous emulsion polymerization is to be set to a controlled size (in this regard, see, for example, US-A 2520959 and US-A 3397165).
  • a polymer seed whose polymer seed particles have a weight-average diameter Dw ⁇ 100 nm, frequently > 5 nm to ⁇ 50 nm, and often > 15 nm to ⁇ 35 nm.
  • the weight-average particle diameters Dw are generally determined according to ISO 13321 using a High Performance Particle Sizer from Malvern, at 22°C and a wavelength of 633 nm.
  • the polymer seed is used customarily in the form of an aqueous polymer dispersion.
  • an exogenous polymer seed is understood to be a polymer seed which has been prepared in a separate reaction step and has a monomeric composition differing from that of the polymer prepared by the radically initiated aqueous emulsion polymerization, although this means nothing more than that different monomers, or monomer mixtures having a differing composition, are used for preparing the exogenous polymer seed and for preparing the aqueous polymer dispersion.
  • an exogenous polymer seed is used that has a glass transition temperature > 50°C, frequently > 60°C or > 70°C, and often > 80°C or > 90°C.
  • a polystyrene or polymethyl methacrylate polymer seed is especially preferred.
  • the total amount of exogenous polymer seed may be included in the initial charge to the polymerization vessel. Another possibility, however, is to include only a portion of the exogenous polymer seed in the initial charge in the polymerization vessel, and to add the remainder during the polymerization together with the monomers. If necessary, however, it is also possible to add the total amount of polymer seed in the course of the polymerization.
  • the total amount of exogenous polymer seed is preferably included in the initial charge to the polymerization vessel before the polymerization reaction is initiated.
  • the aqueous dispersion of a hydroxy-functional polymer P has a solids content in the range of > 35 and
  • the solids content here is determined by drying an aliquot amount (around 1 g) of the aqueous dispersion to constant weight at a temperature of 120°C in an aluminum dish having an internal diameter of around 5 cm.
  • the polyisocyanate component (I) and the polyacrylate component (ii) are mixed with one another.
  • Mixing is accomplished customarily by the stirred incorporation of the polyisocyanate component into the polyacrylate component, or of the polyacrylate component into the polyisocyanate component.
  • the mixing of the polyisocyanate component and the polyacrylate component may in principle take place according to various methods, as for example by stirred incorporation by hand, by shaking, by stirred incorporation by laboratory stirrer at defined rotary speeds, and, in the case of spray applications, by the combining and mixing of the two components within the spraying nozzle.
  • Mixing is preferably accomplished by means of mechanically stirred incorporation.
  • the various methods differ in relation to the shearing, and certain mixing methods are suitable only for systems (isocyanates and formulated dispersions) with sufficient stabilization and appropriate rheological characteristics.
  • the molar ratio of the isocyanate groups in the polyisocyanate component to the hydroxyl groups in the hydroxyfunctional polymer P is generally from 0.2:1 to 5:1, preferably 0.8:1 to 2.5:1, and especially 0.9:1 to 2.0:1.
  • the two-component coating composition is especially suitable for use in coating materials and paints.
  • the two-component coating composition may additionally comprise pigments, fillers, dispersants, thickeners, preservatives, film-forming assistants, flow control and wetting assistants, solvents, neutralizing agents, defoamers, light stabilizers and/or corrosion inhibitors. These additives are preferably part of the component (ii).
  • Pigments which can be used in this context include in principle all organic and/or inorganic white and/or chromatic pigments familiar to a person skilled in the art and having a particle size ⁇ 10 000 nm (Brock, Groteklaes, Mischke, Lehrbuch der Lacktechnologie 2 nd edition, Ed. U. Zorll, Vincentz Verlag 1998, p.113).
  • chromatic pigments familiar to a person skilled in the art may be used for providing color, examples being the relatively inexpensive inorganic iron, cadmium, chromium, and lead oxides and sulfides, lead molybdate, cobalt blue or carbon black, and also the relatively expensive organic pigments, examples being phthalocyanines, azo pigments, quinacridones, perylenes or carbazoles.
  • the two-component coating composition may of course further comprise fillers, as they are known, which are familiar to a person skilled in the art.
  • Fillers are understood essentially to be inorganic materials in powder form with a particle size ⁇ 10 000 nm (Brock, Groteklaes, Mischke, Lehrbuch der Lacktechnologie 2 nd edition, Ed. U. Zorll, Vincentz Verlag 1998, p.113) having a refractive index lower by comparison with the pigments (white fillers according to DIN 55943 and DIN 55945 have refractive index values ⁇ 1.7).
  • the fillers in powder form here are often naturally occurring minerals, such as, for example, calcite, chalk, dolomite, kaolin, talc, mica, diatomaceous earth, baryte, quartz or talc/chlorite intergrowths, and also synthetically prepared inorganic compounds, such as, for example, precipitated calcium carbonate, calcined kaolin, or barium sulfate, and also fumed silica.
  • a preferred filler used is calcium carbonate in the form of the crystalline calcite or the amorphous chalk.
  • Corrosion inhibitors contemplated in accordance with the invention are, in particular, corrosion inhibitors or anticorrosion pigments.
  • corrosion inhibitors examples include hexamine, benzotri azole, phenylenediamine, dimethylethanolamine, polyaniline, sodium nitrite, cinnamaldehyde, condensation products of aldehydes and amines (imines), chromates, nitrites, phosphates, hydrazine, and ascorbic acid.
  • anticorrosion pigments are modified zinc orthophosphates (for example HEUCOPHOS® ZPA, ZPO and ZMP), polyphosphates (for example HEUCOPHOS® ZAPP, SAPP, SRPP and CAPP), WSA - Wide Spectrum Anticorrosives (for example HEUCOPHOS® ZAMPLUS and ZCPPLUS) and modified silicate pigments (for example HEUCOSIL® CTF, Halox® 750), for example from the company Heubach GmbH, and also barium boron phosphate (for example Halox® 400), barium phosphosilicates (for example Halox® BW-111, Halox® BW-191), calcium borosilicates (for example Halox® CW-291, CW-22/221, CW-2230), calcium phosphosilicate (for example Halox® CW-491), strontium phosphosilicate (for example Halox® SW-111) or strontium zinc phosphosilicate (for example Halox® SZP-391) from the company Halox
  • Drying is familiar to a person skilled in the art and is accomplished for example in a tunnel oven or by flashing off. Drying may also take place by means of NIR radiation, with NIR radiation referring here to electromagnetic radiation in the wavelength range from 760 nm to 2.5 pm, preferably from 900 to 1500 nm. Drying may take place at a temperature from ambient temperature up to 100°C over a period of a few minutes to several days.
  • NIR radiation referring here to electromagnetic radiation in the wavelength range from 760 nm to 2.5 pm, preferably from 900 to 1500 nm. Drying may take place at a temperature from ambient temperature up to 100°C over a period of a few minutes to several days.
  • the two-component coating compositions are suitable for coating substrates such as wood, wood veneer, paper, paperboard, card, textile, film, leather, nonwoven, polymer surfaces, glass, ceramic, mineral building materials such as molded cement bricks and fiber cement plates or metals, which can in each case optionally be precoated or pretreated.
  • substrates such as wood, wood veneer, paper, paperboard, card, textile, film, leather, nonwoven, polymer surfaces, glass, ceramic, mineral building materials such as molded cement bricks and fiber cement plates or metals, which can in each case optionally be precoated or pretreated.
  • the two-component coating composition is used for coating metal, wood, plastic, and glass.
  • Such coating compositions are suitable as or in interior or exterior coatings, i.e., applications which are exposed to daylight, preferably parts of buildings, coatings on (large) vehicles and aircraft and industrial applications, such as commercial vehicles in the agricultural (ACE) and building sector, decorative surface coatings, bridges, buildings, electric pylons, tanks, containers, pipelines, power stations, chemical plants, ships, cranes, posts, sheet pile walls, valves, pipes, fittings, flanges, couplings, halls, roofs and structural steel, furniture, windows, doors, parquetry floors, can coating and coil coating, for floor coverings as in the case of parking decks or in hospitals, in automobile paints as OEM and refinishing.
  • ACE agricultural
  • coating compositions are suitable as or in interior or exterior coatings, i.e., applications which are exposed to daylight, preferably parts of buildings, coatings on (large) vehicles and aircraft and industrial applications, such as commercial vehicles in the agricultural (ACE) and building sector, decorative surface coatings, bridges, buildings, electric pylons
  • the coating compositions according to the invention are used as clearcoat materials, pigmented and/or equipped with filling media, in primer systems or in basecoat, intercoat or topcoat materials.
  • Coating compositions of this kind are used preferably at temperatures from ambient temperature to 80°C, preferably from 5°C to 60°C, more preferably from 10°C to 40°C.
  • the articles in question are preferably those which cannot be cured at high temperatures, such as large machines, aircraft, large-capacity vehicles, and refinish applications.
  • Coating of the substrates is carried out by conventional methods known to those skilled in the art, with at least one coating composition being applied in the desired thickness to the substrate to be coated and the volatile constituents optionally comprised in the coating composition being removed, optionally by heating. This procedure can, if desired, be repeated one or more times.
  • Application to the substrate can be carried out in a known manner, e.g., by spraying, troweling, knife coating, brushing, application by roller, rolling, casting, laminating, backspraying or coextrusion.
  • the thickness of such a layer to be cured can be from 0.1 pm to a number of mm, preferably from 1 to 2000 pm, particularly preferably from 5 to 200 pm, very particularly preferably from 5 to 60 pm (based on the material coating composition in the state in which the solvent has been removed from the material coating composition). Examples materials used in the examples were as follows:
  • Basonol® AC 2120 W (from BASF) aqueous dispersion of a polyacrylate polyol with OH number of 120 mg KOH/g (calculated); approx. 42% by wt. in water/3-butoxypropan-2-ol (51.4/6.6)
  • Bayhydrol® A 145 (From Covestro) Aqueous polyacrylate polyol with OH number of 109 mg KOH/g.;
  • Joncryl® OH 8710 (From BASF) Aqueous polyacrylate polyol with OH number of 125 mg KOH/g.; Approx. 46% by wt. in water.
  • Basonat® HI 3000 (from BASF) low viscous asymmetric isocyanurate based on HDI, which is without any modification with anionic group
  • Basonat® HI 2000 (from BASF) low viscous HDI-based polyisocyanate, which is without any modification with anionic group
  • Hydropalat® WE 3650 (from BASF) wetting agent EFKA® SL 3035 (from BASF) slip/leveling agent
  • Solvenon® PnB (from BASF) 3-butoxypropan-2-ol (solvent), Rhodiasolv® RPDE (from Solvay) solvent
  • the coated glass plates were dried at 23 °C, and the pendulum hardness was measured after 2 h, 4 h, 1 d, 7 d. After 7 days, the glass plates were additionally heated to 40 °C, or 60 °C respectively (cf., tables) for 15 hours, and after cooling to 23 °C, the pendulum hardness was measured again.
  • the pendulum hardness was measured according to DIN EN ISO 1522:2006 using the Kbnig pendulum.
  • the coating composition was applied with a draw down bar on two glass plates to get a wet film thickness of 150 pm. Fix both freshly coated glass plates onto the sand test device. Then the sand filled metal cone with its two wheels on the coating was placed and the sand vent was opened to allow for a thin sand flow to start. The sand filled metal cone on wheels moved at constant velocity of 1 cm per hour over the wet film. After 24 h the sand test device was turned off, the sand vent was closed and the cone from the testing plates was removed. The sand from the plates was shaken off. Using the brush, sand corns which were lying on the coating but are not really sticking to it were carefully removed. The length of the sand path until the very last sand corn was measured with the ruler and converted to the time which is designated as sand drying time.
  • the component A1 was prepared by mixing all the components under mechanical mixing. To the 700 g of Basonol AC 2120 W, 9.8 g 1 : 1 mixture of N,N - dimethylethanolamine (DMEA) : water was added followed by 40 g of deionized water. Subsequently, 9.03 g of Hydropalat® WE 3650 (from BASF; wetting agent) and 3.01 g of EFKA® SL 3035 (from BASF; slip/leveling agent) was added. The mixture was stirred at 400 rpm for 5 minutes, and then was left standing for 12 hours to give the readily formulated component A.
  • DMEA N,N - dimethylethanolamine
  • Basonat® HI 3000 low viscous HDI-based polyisocyanate
  • Basonat® HI 2000 (HDI-based polyisocyanate) was dissolved in Rhodiasolv® RPDE (from Solvay) to give a 65 wt-% solution. The mixture was mixed for 2 minutes at 600 rpm.
  • Table 2 Pendulum hardness and drying times of clearcoats of Component A1 and Component B1 to B4 and B8
  • the inventive example CC-A1 B3 in comparison to CC-A1 B4 show faster drying while maintaining gloss at 20° angle.
  • CC-A1 B1 , and CC-A1 B2 showed faster drying but at the cost of considerable loss of gloss.
  • CC-A1 B8 showed slower drying and lower gloss as compared to the inventive example CC-A1 B3.
  • the component A2 was prepared by mixing all the components under mechanical mixing. To the 300 g of Bayhydrol® A 145, 1.5 g 1 : 1 mixture of N,N - dimethylethanolamine (DMEA) : water was added followed by 5 g of deionized water. Subsequently, 3.74 g of Hydropalat® WE 3650 (from BASF; wetting agent) and 1.35 g of EFKA® SL 3035 (from BASF; slip/leveling agent) was added. The mixture was stirred at 400 rpm for 5 minutes, and then was left standing for 12 hours to give the readily formulated component A.
  • DMEA N,N - dimethylethanolamine
  • component A2 Under mixing at 600 rpm, to 50 g of component A2, 17.7 g of respective component B (corresponds to an isocyanate index of 150, i.e., 1.5 NCO groups of hardener per 1 OH group of binder) was added. The mixture was stirred at 1200 rpm for 2 min and 5 g water was added and mixed to give the clear coat, which can be applied after waiting for 30 min.
  • Different clearcoats were prepared using Component A2 with variation in Component B used, i.e. Component B5, Component B6, Component B7 and Component B9 to give corresponding clearcoats respectively CC- A2B5, CC-A2B6, CC-A2B7 and CC-A2B9 (Table 3).
  • inventive example CC-A2B6 in comparison to CC-A2B5 and CC-A2B7 showed faster drying while maintaining gloss at 20° angle.
  • inventive example CC-A2B6 showed faster drying and better gloss as compared to CC- A2B9.
  • the component A3 was prepared by mixing all the components under mechanical mixing. To the 300 g of Joncryl OH 8710, 1.35 g 1 : 1 mixture of N,N - dimethylethanolamine (DMEA) : water was added followed by 5 g of deionized water. To this 22.95 g Solvenon® PnB (From BASF) added slowly in 2 min. Subsequently, 4.05 g of Hydropalat® WE 3650 (from BASF; wetting agent) and 1.35 g of EFKA® SL 3035 (from BASF; slip/leveling agent) was added. The mixture was stirred at 400 rpm for 5 minutes, and then was left standing for 12 hours to give the readily formulated component A.
  • DMEA N,N - dimethylethanolamine
  • the component A4 was prepared by mixing all the components under mechanical mixing. To the 300 g of Basonol® AC 2120 W, 4.70 g 1 : 1 mixture of N,N - dimethylethanolamine (DMEA) : water was added followed by 17 g of deionized water. Subsequently, 3.92 g of Hydropalat® WE 3650 (from BASF; wetting agent) and 1 .35 g of EFKA® SL 3035 (from BASF; slip/leveling agent) was added. The mixture was stirred at 400 rpm for 5 minutes, and then was left standing for 12 hours to give the readily formulated component A.
  • DMEA N,N - dimethylethanolamine
  • component A4 Under mixing at 600 rpm, to 50 g of component A4, 16.14 g of respective component B (corresponds to an isocyanate index of 135, i.e., 1.35 NCO groups of hardener per 1 OH group of binder) was added. The mixture was stirred at 1200 rpm for 2 min and 8 g water was added and mixed to give the clear coat, which can be applied after waiting for 30 min.
  • Different clearcoats were prepared using Component A4 with variation in Component B used, i.e. Component B5, Component B6, Component B7 and Component B9 to give corresponding clearcoats respectively CC-A4B5, CC-A4B6, CC-A4B7 and CC-A4B9 (Table 7).
  • inventive example CC-A4B6 in comparison to CC-A4B5 and CC-A4B7 showed faster drying while maintaining gloss at 20° angle.
  • inventive example CC-A4B6 in comparison to CC-A4B9 showed better gloss at comparable drying time.

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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)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition de revêtement à deux composants comprenant un composant (i) qui est une composition comprenant ia) au moins un polyisocyanate et ib) au moins une γ-lactone, qui porte 1 ou 2 radicaux choisis parmi C1-C6 alkyle, C1-C6-alcoxy et méthylcarboxylate-C1-C4 alkyle et le composant (ii) comprenant au moins une dispersion aqueuse d'un polymère à fonction hydroxy P, son procédé de production et son utilisation pour le revêtement de métal, de bois, de plastique et de verre.
PCT/EP2024/080032 2023-10-30 2024-10-24 Composition de revêtement à deux composants Pending WO2025093409A1 (fr)

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EP23206678 2023-10-30
EP23206678.7 2023-10-30

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Citations (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2520959A (en) 1945-11-06 1950-09-05 Goodrich Co B F Polymerization of vinyl compounds
US3397165A (en) 1964-05-04 1968-08-13 Grace W R & Co Preparation of latex of butadienecontaining copolymers
EP0126300A1 (fr) 1983-04-23 1984-11-28 BASF Aktiengesellschaft Procédé à plusieurs étapes pour la fabrication de 3-isocyanatométhyl-3,5,5-triméthyl-cyclohexylisocyanate
EP0126299A1 (fr) 1983-04-23 1984-11-28 BASF Aktiengesellschaft Procédé à plusieurs étapes pour la préparation d'hexaméthylènediisocyanate et/ou diisocyanates isomériques aliphatiques
EP0355443A2 (fr) 1988-08-18 1990-02-28 Hüls Aktiengesellschaft Procédé cyclique pour la préparation de diisocyanates (cyclo)aliphatiques
DE4003422A1 (de) 1990-02-06 1991-08-08 Basf Ag Waessrige polyurethanzubereitungen
WO1994003516A1 (fr) 1992-08-08 1994-02-17 Herberts Gesellschaft mit beschränkter Haftung Agent de recouvrement diluable dans l'eau, a base de polyacrylates et de polyisocyanates
EP0697424A1 (fr) 1994-08-19 1996-02-21 Basf Aktiengesellschaft Mélanges contenant des isocyanates émulsionnables dans l'eau
DE19624299A1 (de) 1995-06-30 1997-01-02 Basf Ag Verfahren zur Entfernung organischer Verbindungen aus Dispersionen und Vorrichtung zu dessen Durchführung
EP0771328A1 (fr) 1994-06-03 1997-05-07 Basf Aktiengesellschaft Procede de preparation d'une dispersion polymere aqueuse
DE19621027A1 (de) 1996-05-24 1997-11-27 Basf Ag Verfahren zur Abtrennung flüchtiger organischer Komponenten aus Suspensionen oder Dispersionen
DE19741184A1 (de) 1997-09-18 1999-03-25 Basf Ag Verfahren zur Verminderung von Restmonomeren in Flüssigsystemen unter Zugabe eines Redoxinitiatorsystems
DE19741187A1 (de) 1997-09-18 1999-03-25 Basf Ag Verfahren zur Verminderung des Restmonomerengehalts in wässrigen Polymerdispersionen
DE19805122A1 (de) 1998-02-09 1999-04-22 Basf Ag Verfahren zur Herstellung wässriger Polymerisatdispersionen mit geringem Restmonomerengehalt
DE19828183A1 (de) 1998-06-24 1999-12-30 Basf Ag Verfahren zur Entfernung von restflüchtigen Komponenten aus Polymerdispersionen
DE19839199A1 (de) 1998-08-28 2000-03-02 Basf Ag Verfahren zur Verminderung der Restmonomerenmenge in wässrigen Polymerdispersionen
DE19840586A1 (de) 1998-09-05 2000-03-09 Basf Ag Verfahren zur Verminderung der Restmonomerenmenge in wässrigen Polymerdispersionen
DE19847115C1 (de) 1998-10-13 2000-05-04 Basf Ag Gegenstrom-Stripprohr
DE10013186A1 (de) 2000-03-17 2001-09-20 Basf Ag Polyisocyanate
DE10013187A1 (de) 2000-03-17 2001-10-11 Basf Ag Hochfunktionelle Polyisocyanata
WO2005087828A1 (fr) 2004-03-12 2005-09-22 Basf Aktiengesellschaft Procede de preparation de polyisocyanates contenant des groupes isocyanurate et utilisation desdits composes
WO2008068198A1 (fr) 2006-12-04 2008-06-12 Basf Se Procédé de production de polyisocyanates
WO2022069561A1 (fr) * 2020-09-30 2022-04-07 Covestro Deutschland Ag Polyisocyanate modifié
US11639447B2 (en) * 2011-11-29 2023-05-02 Axalta Coating Systems Ip Co., Llc Coating installation of an industrial mass production coating line including non-aqueous solvent composition as barrier liquid

Patent Citations (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2520959A (en) 1945-11-06 1950-09-05 Goodrich Co B F Polymerization of vinyl compounds
US3397165A (en) 1964-05-04 1968-08-13 Grace W R & Co Preparation of latex of butadienecontaining copolymers
EP0126300A1 (fr) 1983-04-23 1984-11-28 BASF Aktiengesellschaft Procédé à plusieurs étapes pour la fabrication de 3-isocyanatométhyl-3,5,5-triméthyl-cyclohexylisocyanate
EP0126299A1 (fr) 1983-04-23 1984-11-28 BASF Aktiengesellschaft Procédé à plusieurs étapes pour la préparation d'hexaméthylènediisocyanate et/ou diisocyanates isomériques aliphatiques
US4596679A (en) 1983-04-23 1986-06-24 Basf Aktiengesellschaft Multiple-step process for the preparation of 3-isocyanatomethyl-3,5,5-trimethylcyclohexylisocyanate
US4596678A (en) 1983-04-23 1986-06-24 Basf Aktiengesellschaft Multiple-step process for the preparation of hexamethylene diisocyanate-1,6 and/or isomeric aliphatic diisocyanates with six carbon atoms in the alkylene residue
EP0355443A2 (fr) 1988-08-18 1990-02-28 Hüls Aktiengesellschaft Procédé cyclique pour la préparation de diisocyanates (cyclo)aliphatiques
US5087739A (en) 1988-08-18 1992-02-11 Huels Aktiengesellschaft Circulation process for the production of aliphatic and cycloaliphatic diisocyanates
DE4003422A1 (de) 1990-02-06 1991-08-08 Basf Ag Waessrige polyurethanzubereitungen
WO1994003516A1 (fr) 1992-08-08 1994-02-17 Herberts Gesellschaft mit beschränkter Haftung Agent de recouvrement diluable dans l'eau, a base de polyacrylates et de polyisocyanates
EP0771328A1 (fr) 1994-06-03 1997-05-07 Basf Aktiengesellschaft Procede de preparation d'une dispersion polymere aqueuse
EP0697424A1 (fr) 1994-08-19 1996-02-21 Basf Aktiengesellschaft Mélanges contenant des isocyanates émulsionnables dans l'eau
EP0697424B2 (fr) * 1994-08-19 2002-07-03 Basf Aktiengesellschaft Mélanges contenant des isocyanates émulsionnables dans l'eau
DE19624299A1 (de) 1995-06-30 1997-01-02 Basf Ag Verfahren zur Entfernung organischer Verbindungen aus Dispersionen und Vorrichtung zu dessen Durchführung
DE19621027A1 (de) 1996-05-24 1997-11-27 Basf Ag Verfahren zur Abtrennung flüchtiger organischer Komponenten aus Suspensionen oder Dispersionen
DE19741184A1 (de) 1997-09-18 1999-03-25 Basf Ag Verfahren zur Verminderung von Restmonomeren in Flüssigsystemen unter Zugabe eines Redoxinitiatorsystems
DE19741187A1 (de) 1997-09-18 1999-03-25 Basf Ag Verfahren zur Verminderung des Restmonomerengehalts in wässrigen Polymerdispersionen
DE19805122A1 (de) 1998-02-09 1999-04-22 Basf Ag Verfahren zur Herstellung wässriger Polymerisatdispersionen mit geringem Restmonomerengehalt
DE19828183A1 (de) 1998-06-24 1999-12-30 Basf Ag Verfahren zur Entfernung von restflüchtigen Komponenten aus Polymerdispersionen
DE19839199A1 (de) 1998-08-28 2000-03-02 Basf Ag Verfahren zur Verminderung der Restmonomerenmenge in wässrigen Polymerdispersionen
DE19840586A1 (de) 1998-09-05 2000-03-09 Basf Ag Verfahren zur Verminderung der Restmonomerenmenge in wässrigen Polymerdispersionen
DE19847115C1 (de) 1998-10-13 2000-05-04 Basf Ag Gegenstrom-Stripprohr
DE10013186A1 (de) 2000-03-17 2001-09-20 Basf Ag Polyisocyanate
DE10013187A1 (de) 2000-03-17 2001-10-11 Basf Ag Hochfunktionelle Polyisocyanata
WO2005087828A1 (fr) 2004-03-12 2005-09-22 Basf Aktiengesellschaft Procede de preparation de polyisocyanates contenant des groupes isocyanurate et utilisation desdits composes
WO2008068198A1 (fr) 2006-12-04 2008-06-12 Basf Se Procédé de production de polyisocyanates
US11639447B2 (en) * 2011-11-29 2023-05-02 Axalta Coating Systems Ip Co., Llc Coating installation of an industrial mass production coating line including non-aqueous solvent composition as barrier liquid
WO2022069561A1 (fr) * 2020-09-30 2022-04-07 Covestro Deutschland Ag Polyisocyanate modifié

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
"Corrosion Inhibitors, 2nd Edition. An industrial Guide", WILLIAM ANDREW INC.
"Emulsion Polymerization in Encyclopedia of Polymer Science and Engineering", vol. 19, 1987, pages: 62 - 65
"Emulsion Polymerization", 1965, INTERSCIENCE PUBLISHERS
BROCKGROTEKLAESMISCHKELEHRBUCH: "Lehrbuch der Lacktechnologie", 1998, VINCENTZ VERLAG, pages: 113
D. A. WICKSZ. W. WICKS, PROGRESS IN ORGANIC COATINGS, vol. 36, 41, 43, 1999, pages 148 - 172,1-83,131-140
D. DIEDERICH, CHEMIE IN UNSERER ZEIT, vol. 24, 1990, pages 135 - 142
D.C. BLACKLEY, HIGH POLYMER LATICES, vol. 1, 1966, pages 35
H. WARSON, THE APPLICATIONS OF SYNTHETIC RESIN EMULSIONS, 1972, pages 246
HOUBEN-WEYL: "Makromolekulare Stoffe [Macromolecular compounds", vol. XIV/1, 1961, GEORG-THIEME-VERLAG, article "Methoden der organischen Chemie", pages: 192 - 208
J. BRANDRUPE.H. IMMERGUT: "Polymer Handbook", 1989, JOHN WILEY & SONS, pages: 133 - 141
SHANTA DUTTAIRIS K.M. YUDANIEL C.W. TSANGYUN HAU NGYONG SIK OKJAMES SHERWOODJAMES H. CLARK: "Green synthesis of gamma-verolactone through hydrogenation of biomass-derived levulinic acid using non-noble metal catalysts", CHEMICAL ENGINEERING JOURNAL, vol. 372, 2019, pages 992 - 1006, XP085695795, DOI: 10.1016/j.cej.2019.04.199

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