DE102014016763A1 - Low-VOC coalescents for aqueous dispersions - Google Patents

Low-VOC coalescents for aqueous dispersions Download PDF

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DE102014016763A1
DE102014016763A1 DE102014016763.1A DE102014016763A DE102014016763A1 DE 102014016763 A1 DE102014016763 A1 DE 102014016763A1 DE 102014016763 A DE102014016763 A DE 102014016763A DE 102014016763 A1 DE102014016763 A1 DE 102014016763A1
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pigment
dispersion
dispersion according
formula
pigment red
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Rainer Kupfer
Christoph Söffing
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Clariant International Ltd
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Clariant International Ltd
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Priority to DE202014010355.0U priority patent/DE202014010355U1/en
Publication of DE102014016763A1 publication Critical patent/DE102014016763A1/en
Priority to PCT/EP2015/073616 priority patent/WO2016074874A1/en
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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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • B32B5/08—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer the fibres or filaments of a layer being of different substances, e.g. conjugate fibres, mixture of different fibres
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    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/16—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer formed of particles, e.g. chips, powder or granules
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    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
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    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
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    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
    • B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/30—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being formed of particles, e.g. chips, granules, powder
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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B68—SADDLERY; UPHOLSTERY
    • B68G—METHODS, EQUIPMENT, OR MACHINES FOR USE IN UPHOLSTERING; UPHOLSTERY NOT OTHERWISE PROVIDED FOR
    • B68G11/00—Finished upholstery not provided for in other classes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B68—SADDLERY; UPHOLSTERY
    • B68G—METHODS, EQUIPMENT, OR MACHINES FOR USE IN UPHOLSTERING; UPHOLSTERY NOT OTHERWISE PROVIDED FOR
    • B68G7/00—Making upholstery
    • B68G7/02—Making upholstery from waddings, fleeces, mats, or the like
    • B68G7/04—Making upholstery from waddings, fleeces, mats, or the like by conveyor-line methods
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
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    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/16—Powdering or granulating by coagulating dispersions
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
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    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
    • B32B2262/02—Synthetic macromolecular fibres
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
    • B32B2262/12—Conjugate fibres, e.g. core/sheath or side-by-side
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
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    • B32B2264/00—Composition or properties of particles which form a particulate layer or are present as additives
    • B32B2264/02—Synthetic macromolecular particles
    • B32B2264/0214—Particles made of materials belonging to B32B27/00
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    • B32—LAYERED PRODUCTS
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    • B32B2264/00—Composition or properties of particles which form a particulate layer or are present as additives
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    • B32B2264/0292—Polyurethane particles
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    • B32B2479/00—Furniture
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
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    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
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    • C—CHEMISTRY; METALLURGY
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    • C08K5/00—Use of organic ingredients
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    • C08K5/05—Alcohols; Metal alcoholates
    • C08K5/053—Polyhydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
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  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Dispersion Chemistry (AREA)
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Abstract

Gegenstand der Erfindung ist eine Dispersion enthaltend (A) mindestens eine Verbindung der Formel (I)worin R1 für eine Kohlenwasserstoffgruppe mit 7 bis 21 Kohlenstoffatomen steht, (B) einen polymeren Binder und (C) Wasser.The invention relates to a dispersion comprising (A) at least one compound of formula (I) wherein R 1 is a hydrocarbon group having 7 to 21 carbon atoms, (B) a polymeric binder and (C) water.

Description

Die vorliegende Erfindung betrifft die Verwendung von Polyhydroxyfettsäureamiden als VOC-arme Koaleszensmittel zur Beschichtung von Substraten, insbesondere durch wässrige Dispersionen.The present invention relates to the use of polyhydroxy fatty acid amides as low-VOC coalescents for coating substrates, in particular by aqueous dispersions.

Wässrige Polymerdispersionen, wie sie für Dispersionsfarben verwendet werden, dienen als Schutzfilm für das Substrat, auf das sie appliziert werden. Dazu müssen alle flüchtigen Komponenten, insbesondere Wasser verdampfen, so dass der Polymerlatex zu einem Film verschmilzt und die farbigen oder weißen Pigmente, Füllstoffe und Additive einschließt. Die Mindestfilmbildetemperatur (MFT) beschreibt die niedrigste Temperatur, bei der sich noch ein zusammenhängender Film bildet. Diese kann durch Zusatz von Koaleszensmittel (auch Verfilmungs- oder Filmbildehilfsmittel genannt) herabgesetzt werden. Die Filmbildung soll auch bei Temperaturen unterhalb von 20°C, vorzugsweise bei Temperaturen von 5°C oder geringer einsetzten, damit die Dispersionsfarbe über einen breiteren Temperaturbereich applizierbar bleibt.Aqueous polymer dispersions, as used for emulsion paints, serve as a protective film for the substrate to which they are applied. To do this, all of the volatile components, especially water, must volatilize, so that the polymer latex melts into a film and includes the colored or white pigments, fillers, and additives. The minimum film-forming temperature (MFT) describes the lowest temperature at which a coherent film forms. This can be reduced by the addition of coalescing agents (also called filming or film-forming aids). The film formation should also be used at temperatures below 20 ° C., preferably at temperatures of 5 ° C. or lower, so that the emulsion paint remains administrable over a broader temperature range.

Koaleszensmittel wie z. B. Butylglykol, Butyldiglykol, Butyldipropylenglykol u. a. werden in Patent WO-0179140 beschrieben.Coalescing agents such. As butyl glycol, butyl diglycol, Butyldipropylenglykol and others are in patent WO-0179140 described.

US-2218237 beschreibt Diethylenglykolbenzoat als Koaleszensmittel für Polyvinylacetat-Harze. US 2218237 describes diethylene glycol zoate as a coalescing agent for polyvinyl acetate resins.

Die MFT von Dispersionsfarben mit Polymerdispersionen auf Basis von Methacrylsäure und Acrylsäureestern oder Polyvinylacetat kann durch Zusatz von Trimethylpentan-1,3-diol-monoisobutyrat herabgesetzt werden. Die Synthese und Anwendung des Koalsezensmittels wird in US-3091632 und US-3312652 beschrieben.The MFT of emulsion paints with polymer dispersions based on methacrylic acid and acrylic esters or polyvinyl acetate can be reduced by adding trimethylpentane-1,3-diol monoisobutyrate. The synthesis and application of Koalsezensmittels is in US 3091632 and US 3312652 described.

US-5236987 beschreibt Isodecylbenzoat als Weichmacher und Koaleszensmittel für Polyvinylchlorid-Plastisole. WO-2005/026249 beschreibt Isononylbenzoat als Koaleszensmittel für Anstrichstoffe und Klebstoffe. US 5236987 describes isodecyl benzoate as a plasticizer and coalescing agent for polyvinyl chloride plastisols. WO-2005/026249 describes isononyl benzoate as a coalescing agent for paints and adhesives.

DE-10 2010 005 973 und WO-2005049719 beschreiben die Verwendung von Milchsäureestern von Fettalkoholen als Koaleszensmittel für Dispersionsfarben. DE-10 2010 005 973 and WO-2005049719 describe the use of lactic acid esters of fatty alcohols as coalescing agents for emulsion paints.

Die Verwendung von Glutarsäure-, Adipinsäure- und Bernsteinsäure-Diestern von C4-C8-Alkoholen als Koaleszensmittel wird in US-8106239 beschrieben.The use of glutaric, adipic and succinic diesters of C 4 -C 8 -alcohols as coalescing agents is described in US Pat US 8106239 described.

WO-2012069098 beschreibt die Verwendung von C4-C8 Monocarbonsäureestern der Alkohole der Pentanole und DE-10 2007 021 139 die Verwendung von Fettsäure-Methanolestern, -Ethanolestern, -n-Propanolestern und -iso-Propanolerstern als Koalszensmittel. WO-2012069098 describes the use of C 4 -C 8 monocarboxylic acid esters of the alcohols of the pentanols and DE-10 2007 021 139 the use of fatty acid-methanol esters, -ethanol esters, -n-propanol esters and -iso-Propanolerstern as Koalszensmittel.

Unter anderem US-4435534 , US-2003/204003 , US-4525512 sowie WO-0056823 beschreiben verschiedene niedermolekulare Alkylenglykole und deren Ester und Ether, die als Koalszensmittel verwendet werden können.Amongst other things US 4435534 . US 2003/204003 . US 4525512 such as WO-0056823 describe various low molecular weight alkylene glycols and their esters and ethers which can be used as Koalszensmittel.

Als vielverwendeter technischer Standard ist „Texanol” (2,2,4-Trimethyl-pentan-1,3-diol-mono-iso-butyrat) von der Firma Eastman bekannt.A widely used technical standard is "Texanol" (2,2,4-trimethyl-pentane-1,3-diol mono-iso-butyrate) from Eastman.

US-2002/061940 beschreibt eine VOC freie Beschichtungszusammensetzung, die eine MFT < 5°C besitzt. US 2002 / 061,940 describes a VOC-free coating composition having an MFT <5 ° C.

Nachteil solcher Additive, insbesondere der technischen Standards, die einen Siedepunkt < 250°C besitzen, ist ihr Beitrag zum VOC-Gehalt einer Dispersionsfarbe. Solche flüchtige organische Verbindungen begünstigen zusammen mit UV-Strahlung und NOx die Ozonbildung, so dass in vielen Ländern Verordnungen zur Reduzierung des VOC-Gehalts (z. B. 2004/42/EG) erlassen wurde.Disadvantage of such additives, in particular the technical standards, which have a boiling point <250 ° C, is their contribution to the VOC content of an emulsion paint. Such volatile organic compounds, together with UV radiation and NO x, favor the formation of ozone, so that in many countries regulations for the reduction of the VOC content (eg 2004/42 / EC) were issued.

Polyhydroxyfettsäureamide und deren Anwendungen als nichtionische Tenside werden im Stand der Technik beschrieben.Polyhydroxy fatty acid amides and their applications as nonionic surfactants are described in the prior art.

WO-9412609 lehrt Wasch- und Reinigungsmittel, die Polyhydroxyfettsäureamide mit guter reinigender Wirkung gegen fettige Anschmutzungen auf Textilien und Geschirr aufweisen. WO-9412609 teaches washing and cleaning agents which have polyhydroxy fatty acid amides with good cleaning action against greasy soiling on textiles and dishes.

Ein nicht ätzendes, Polyhydroxyfettsäureamide enthaltendes Reinigungsmittel wird in WO-9841601 beschrieben und eignet sich insbesondere zur Beseitigung von öligem und fettigen Schmutz von Kochutensilien. A non-caustic cleaning agent containing polyhydroxy fatty acid amides is disclosed in U.S. Pat WO-9841601 described and is particularly suitable for the removal of oily and greasy dirt from cooking utensils.

WO-9523840 lehrt Waschmittel, die aus Polyhydroxyfettsäureamiden bestehen und sich durch guten Farbschutz auszeichnen. WO-9523840 teaches detergents that consist of polyhydroxy fatty acid amides and are characterized by good color protection.

EP-0745719 beschreibt die Verwendung von Kohlehydratderivaten, wie unter anderem Polyhydroxyfettsäureamide als Hilfsmittel zum Färben oder Bedrucken von Fasermaterialien in faserreaktiven Farbstoffen. EP-0745719 describes the use of carbohydrate derivatives, such as, inter alia, polyhydroxy fatty acid amides as auxiliaries for dyeing or printing fiber materials in fiber-reactive dyes.

DE-69811179 lehrt über wässrige Beschichtungszusammensetzungen mit verlängerter Gebrauchsdauer, die Alkylpolyglykoside enthalten. DE-69811179 teaches extended life aqueous coating compositions containing alkyl polyglycosides.

WO-2014/056561 lehrt die Verwendung von Phosphatiden mit Polyhydroxyfettsäureamiden als Dispergiermittel für wässrige, bindemittelfreie Pigmentpräparationen, die zum Färben von makromolekularen Materialien aller Art, wie Lacken und Farben verwendet werden können. WO-2014/056561 teaches the use of phosphatides with polyhydroxy fatty acid amides as dispersants for aqueous binder-free pigment preparations that can be used to color macromolecular materials of all types, such as paints and inks.

DE-19934836 beschreibt die Verwendung von Polyhydroxyfettsäureamiden als Emulgatoren für die Emulsionspolymerisation. DE-19934836 describes the use of polyhydroxy fatty acid amides as emulsifiers for emulsion polymerization.

Die Herstellung entsprechender Polyhydroxyfettsäureamide ist in WO-9206071 , WO-9206073 , WO-9208687 und DE-4322874 hinlänglich beschrieben worden.The preparation of corresponding polyhydroxy fatty acid amides is in WO-9206071 . WO-9206073 . WO-9208687 and DE-4322874 has been described sufficiently.

Aufgabe der vorliegenden Erfindung war es Koaleszensmittel aufzuzeigen, die durch ihren hohen Siedepunkt keinen oder nur einen sehr geringen Beitrag zum VOC-Gehalt aufweisen. Diese Koaleszenzmittel sollen darüber hinaus die MFT auf ≤ 15°C, vorzugsweise auf ≤ 5°C senken.Object of the present invention was to show coalescing agents, which have no or only a very small contribution to the VOC content due to their high boiling point. In addition, these coalescing agents should lower the MFT to ≦ 15 ° C., preferably to ≦ 5 ° C.

Überraschenderweise wurde gefunden, dass Polyhydroxyfettsäureamide langkettiger Fettalkohole die MFT senken und sich zu VOC-armen Dispersionsfarben formulieren lassen.Surprisingly, it has been found that polyhydroxy fatty acid amides of long-chain fatty alcohols lower the MFT and can be formulated into low-VOC emulsion paints.

Gegenstand der Erfindung ist eine VOC-arme Dispersion, enthaltend

  • (A) mindestens einer Verbindung der Formel (I)
    Figure DE102014016763A1_0002
    worin R1 für eine Kohlenwasserstoffgruppe mit 7 bis 21 Kohlenstoffatomen steht,
  • (B) einem polymeren Binder und
  • (C) Wasser.
The invention relates to a low-VOC dispersion containing
  • (A) at least one compound of the formula (I)
    Figure DE102014016763A1_0002
    wherein R 1 is a hydrocarbon group having 7 to 21 carbon atoms,
  • (B) a polymeric binder and
  • (C) water.

Die Dispersion kann darüber hinaus übliche Bestandteile von wässrigen Dispersionsfarben enthalten. Übliche Bestandteile können sein: Pigmente, wobei mit dem Begriff „Pigmente” sowohl Pigmente, als auch Füllstoffe im Weiteren gemeint sind, und Hilfsstoffe. Hilfsstoffe können unter anderem Netz- und Dispergiermittel, Entschäumer, Biozide, Alkali sowie Rheologie-Additive sein.The dispersion may also contain conventional ingredients of aqueous emulsion paints. Typical constituents may be: pigments, where by the term "pigments" are meant both pigments and fillers and adjuvants. Adjuvants may include wetting and dispersing agents, defoamers, biocides, alkalis and rheology additives.

Verbindung (I) ist ein Polyhydroxy-Amid wobei R1 für eine lineare oder verzweigte, gesättigte oder ungesättigte Kohlenwasserstoffgruppe mit 7 bis 21 Kohlenstoffatomen steht. Die Polyhydroxy-Einheit ist eine Hexose, vorzugsweise das Epimer Glukose. Die erfindungsmäßigen Polyhydroxyfettsäureamide (I) können in reiner Form oder als Gemische untereinander vorliegen.Compound (I) is a polyhydroxy amide wherein R 1 is a linear or branched, saturated or unsaturated hydrocarbon group having 7 to 21 carbon atoms. The polyhydroxy moiety is a hexose, preferably the epimer glucose. The polyhydroxy fatty acid amides (I) according to the invention can be present in pure form or as mixtures with one another.

In einer bevorzugten Ausführungsform ist R1 eine aliphatische Gruppe. In einer weiteren bevorzugten Ausführungsform ist R1 eine Alkyl- oder Alkenylgruppe. In einer weiteren bevorzugten Ausführungsform umfasst R1 7 bis 21 Kohlenstoffatome, insbesondere 7 bis 17 Kohlenstoffatome.In a preferred embodiment, R 1 is an aliphatic group. In a further preferred embodiment, R 1 is an alkyl or alkenyl group. In a further preferred embodiment, R 1 comprises 7 to 21 carbon atoms, in particular 7 to 17 carbon atoms.

Die polymeren Binder, Komponente (B), sind vorzugsweise Homo- oder Copolymere olefinisch ungesättigter Monomere. Bevorzugte olefinisch ungesättigte Monomere sind beispielsweise

  • – Vinylmonomere, wie Carbonsäureester des Vinylalkohols, beispielsweise Vinylacetat, Vinylpropionat, Vinylether der Isononansäure oder der Isodecansäure, die auch als C9 und C10-Versaticsäuren bezeichnet werden,
  • – Arylsubstituierte Olefine, wie Styrol und Stilben,
  • – olefinisch ungesättigte Carbonsäureester, wie Methylacrylat, Ethylacrylat, Propylacrylat, n-Butylacrylat, i-Butylacrylat, Pentylacrylat, Hexylacrylat, 2-Ethylhexylacrylat, Tridecyacrylat, Stearylacrylat, Hydroxyethylacrylat, Hydroxypropylacrylat sowie die entsprechenden Methacrylsäureester,
  • – olefinisch ungesättigte Dicarbonsäureester, wie Dimethylmaleinat, Diethylmaleinat, Dipropylmaleinat, Dibutylmaleinat, Dipentylmaleinat, Dihexylmaleinat und Di-2-ethylhexylmaleinat,
  • – olefinisch ungesättigte Carbonsäuren und Dicarbonsäuren, wie Acrylsäure, Methacrylsäure, Itaconsäure, Maleinsäure und Fumarsäure und ihre Natrium-, Kalium- und Ammoniumsalze,
  • – olefinisch ungesättigte Sulfonsäuren und Phosphonsäuren und ihre Alkali- und Ammoniumsalze, wie Vinylsulfonsäure, Vinylphosphonsäure, Acrylamidomethylpropansulfonsäure und ihre Alkali- und Ammonium-, Alkylammonium- und Hydroxyalkylammoniumsalze, Allylsulfonsäure und ihre Alkali- und Ammoniumsalze, Acryloyloxethylphosphonsäure und ihre Ammonium- und Alkalisalze sowie die entsprechenden Methacrylsäurederivate,
  • – olefinisch ungesättigte Amine, Ammoniumsalze, Nitrile und Amide, wie Dimethylaminoethylacrylat, Acryloyloxethyltrimethylammoniumhalide, Acrylnitril, Acrylamid, Methacrylamid, N-Methylacrylamid, N-Ethylacrylamid, N-Propylacrylamid, N-Methylolacrylamid sowie die entsprechenden Methacrylsäurederivate und Vinylmethylacetamid.
The polymeric binders, component (B), are preferably homopolymers or copolymers of olefinically unsaturated monomers. Preferred olefinically unsaturated monomers are, for example
  • Vinyl monomers, such as carboxylic acid esters of vinyl alcohol, for example vinyl acetate, vinyl propionate, vinyl ethers of isononanoic acid or isodecanoic acid, which are also referred to as C 9 and C 10 versatic acids,
  • Aryl-substituted olefins, such as styrene and stilbene,
  • Olefinically unsaturated carboxylic esters, such as methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, i-butyl acrylate, pentyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, tridecyacrylate, stearyl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate and the corresponding methacrylates,
  • Olefinically unsaturated dicarboxylic esters, such as dimethyl maleate, diethyl maleate, dipropyl maleate, dibutyl maleate, dipentyl maleate, dihexyl maleate and di-2-ethylhexyl maleate,
  • Olefinically unsaturated carboxylic acids and dicarboxylic acids, such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and fumaric acid and their sodium, potassium and ammonium salts,
  • Olefinically unsaturated sulfonic acids and phosphonic acids and their alkali metal and ammonium salts, such as vinylsulfonic acid, vinylphosphonic acid, acrylamidomethylpropanesulfonic acid and their alkali metal and ammonium, alkylammonium and hydroxyalkylammonium salts, allylsulfonic acid and its alkali metal and ammonium salts, acryloyloxethylphosphonic acid and its ammonium and alkali metal salts, and the corresponding salts methacrylic acid,
  • - Olefinically unsaturated amines, ammonium salts, nitriles and amides, such as dimethylaminoethyl acrylate, Acryloyloxethyltrimethylammoniumhalide, acrylonitrile, acrylamide, methacrylamide, N-methylacrylamide, N-ethylacrylamide, N-propylacrylamide, N-methylolacrylamide and the corresponding methacrylic acid derivatives and vinylmethylacetamide.

Der Anteil der erfindungsgemäßen Dispersion an polymerem Binder (Bestandteil B) liegt vorzugsweise bei 1 bis 80 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the inventive dispersion of polymeric binder (component B) is preferably from 1 to 80 wt .-%, based on the weight of the dispersion.

Zur Herstellung der erfindungsgemäßen, wässrigen Dispersionen benutztes Wasser, Komponente (C), wird vorzugsweise in Form von destilliertem oder entsalztem Wasser eingesetzt. Auch Trinkwasser (Leitungswasser) und/oder Wasser natürlichen Ursprungs kann eingesetzt werden.Water used to prepare the aqueous dispersions of the invention, component (C), is preferably used in the form of distilled or demineralized water. Also drinking water (tap water) and / or water of natural origin can be used.

Der Anteil der erfindungsgemäßen Dispersion an Wasser liegt vorzugsweise bei 1 bis 80 Gew.-% bezogen auf das Gewicht der Dispersion.The proportion of the dispersion of the invention in water is preferably from 1 to 80 wt .-% based on the weight of the dispersion.

Geeignete Pigmente sind feinteilige, organische oder anorganische Weiß- oder Buntpigmente oder ein Gemisch verschiedener solcher Pigmente.Suitable pigments are finely divided, organic or inorganic white or colored pigments or a mixture of various such pigments.

Als beispielhafte Auswahl besonders bevorzugter organischer Pigmente sind dabei Rußpigmente, wie z. B. Gas- oder Furnaceruße; Monoazo- und Disazopigmente, insbesondere die Color Index Pigmente Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow 83, Pigment Yellow 87, Pigment Yellow 97, Pigment Yellow 111, Pigment Yellow 126, Pigment Yellow 127, Pigment Yellow 128, Pigment Yellow 155, Pigment Yellow 174, Pigment Yellow 176, Pigment Yellow 191, Pigment Yellow 213, Pigment Yellow 214, Pigment Red 38, Pigment Red 144, Pigment Red 214, Pigment Red 242, Pigment Red 262, Pigment Red 266, Pigment Red 269, Pigment Red 274, Pigment Orange 13, Pigment Orange 34 oder Pigment Brown 41; β-Naphthol- und Naphthol AS Pigmente, insbesondere die Colour Index Pigmente Pigment Red 2, Pigment Red 3, Pigment Red 4, Pigment Red 5, Pigment Red 9, Pigment Red 12, Pigment Red 14, Pigment Red 53:1, Pigment Red 112, Pigment Red 146, Pigment Red 147, Pigment Red 170, Pigment Red 184, Pigment Red 187, Pigment Red 188, Pigment Red 210, Pigment Red 247, Pigment Red 253, Pigment Red 254, Pigment Red 256, Pigment Orange 5, Pigment Orange 38 oder Pigment Brown 1; verlackte Azo- und Metallkomplexpigmente, insbesondere die Colour Index Pigmente Pigment Red 48:2, Pigment Red 48:3, Pigment Red 48:4, Pigment Red 57:1, Pigment Red 257, Pigment Orange 68 oder Pigment Orange 70; Benzimidazolinpigmente, insbesondere die Colour Index Pigmente Pigment Yellow 120, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 175, Pigment Yellow 180, Pigment Yellow 181, Pigment Yellow 194, Pigment Red 175, Pigment Red 176, Pigment Red 185, Pigment Red 208, Pigment Violet 32, Pigment Orange 36, Pigment Orange 62, Pigment Orange 72 oder Pigment Brown 25; Isoindolinon- und Isoindolinpigmente, insbesondere die Colour Index Pigmente Pigment Yellow 139 oder Pigment Yellow 173; Phthalocyaninpigmente, insbesondere die Colour Index Pigmente Pigment Blue 15, Pigment Blue 15:1, Pigment Blue 15:2, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Blue 15:6, Pigment Blue 16, Pigment Green 7 oder Pigment Green 36; Anthanthron-, Anthrachinon-, Chinacridon-, Dioxazin-, Indanthron-, Perylen-, Perinon- und Thioindigopigmente, insbesondere die Colour Index Pigmente Pigment Yellow 196, Pigment Red 122, Pigment Red 149, Pigment Red 168, Pigment Red 177, Pigment Red 179, Pigment Red 181, Pigment Red 207, Pigment Red 209, Pigment Red 263, Pigment Blue 60, Pigment Violet 19, Pigment Violet 23 oder Pigment Orange 43; Triarylcarboniumpigmente, insbesondere die Colour Index Pigmente Pigment Red 169, Pigment Blue 56 oder Pigment Blue 61 zu nennen.As an exemplary selection of particularly preferred organic pigments are carbon black pigments, such as. B. gas or Furnaceruße; Monoazo and disazo pigments, in particular the Color Index Pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow® 83, Pigment Yellow® 87, Pigment Yellow® 97, Pigment Yellow® 111, Pigment Yellow® 126, Pigment Yellow® 127, Pigment Yellow® 128, Pigment Yellow® 155, Pigment Yellow® 174, Pigment Yellow® 176, Pigment Yellow® 191, Pigment Yellow® 213, Pigment Yellow 214 Pigment Red 38, Pigment Red 144, Pigment Red 214, Pigment Red 242, Pigment Red 262, Pigment Red 266, Pigment Red 269, Pigment Red 274, Pigment Orange 13, Pigment Orange 34 or Pigment Brown 41; β-naphthol and naphthol AS pigments, in particular the Color Index Pigments Pigment Red 2, Pigment Red 3, Pigment Red 4, Pigment Red 5, Pigment Red 9, Pigment Red 12, Pigment Red 14, Pigment Red 53: 1, Pigment Red Pigment Red 147, Red Pigment Red 147, Red Pigment Red 170, Pigment Red 184, Red Pigment 187, Pigment Red 188, Pigment Red 210, Pigment Red 247, Pigment Red 253, Red Pigment 254, Pigment Red 256, Pigment Orange 5, Pigment Orange 38 or Pigment Brown 1; laked azo and metal complex pigments, in particular the Color Index pigments Pigment Red 48: 2, Pigment Red 48: 3, Pigment Red 48: 4, Pigment Red 57: 1, Pigment Red 257, Pigment Orange 68 or Pigment Orange 70; Benzimidazoline pigments, in particular the Color Index pigments Pigment Yellow 120, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 175, Pigment Yellow 180, Pigment Yellow 181, Pigment Yellow 194, Pigment Red 175, Pigment Red 176, Pigment Red 185, Pigment Red 208 , Pigment Violet 32, Pigment Orange 36, Pigment Orange 62, Pigment Orange 72 or Pigment Brown 25; Isoindolinone and isoindoline pigments, in particular the Color Index pigments Pigment Yellow 139 or Pigment Yellow 173; Phthalocyanine pigments, in particular the Color Index pigments Pigment Blue 15, Pigment Blue 15: 1, Pigment Blue 15: 2, Pigment Blue 15: 3, Pigment Blue 15: 4, Pigment Blue 15: 6, Pigment Blue 16, Pigment Green 7 or Pigment Green 36; Anthanthrone, anthraquinone, quinacridone, dioxazine, indanthrone, perylene, perinone and thioindigo pigments, in particular the Color Index Pigments Pigment Yellow 196, Pigment Red 122, Pigment Red 149, Pigment Red 168, Pigment Red 177, Pigment Red 179, Pigment Red 181, Pigment Red 207, Pigment Red 209, Pigment Red 263, Pigment Blue 60, Pigment Violet 19, Pigment Violet 23 or Pigment Orange 43; Triarylcarboniumpigmente, in particular the Color Index pigments Pigment Red 169, Pigment Blue 56 or Pigment Blue 61 to call.

Geeignete anorganische Pigmente sind beispielsweise Titandioxide, Zinksulfide, Zinkoxide, Eisenoxide, Magnetite, Manganeisenoxide, Chromoxide, Ultramarin, Nickel- oder Chromantimontitanoxide, Mangantitanrutile, Cobaltoxide, Mischoxide des Cobalts und Aluminiums, Rutilmischphasenpigmente, Sulfide der seltenen Erden, Spinelle des Cobalts mit Nickel und Zink, Spinelle basierend auf Eisen und Chrom mit Kupfer Zink sowie Mangan, Bismutvanadate sowie Verschnittpigmente, insbesondere werden die Color Index Pigmente Pigment Yellow 184, Pigment Yellow 53, Pigment Yellow 42, Pigment Yellow Brown 24, Pigment Red 101, Pigment Blue 28, Pigment Blue 36, Pigment Green 50, Pigment Green 17, Pigment Black 11, Pigment Black 33 sowie Pigment White 6 verwendet; auch als Füllstoffe bezeichnete Calciumcarbonate wie natürlich vorkommende Kreide und gefälltes Calciumcarbonat, Dolomit, natürliches Siliciumdioxid (Quarzmehl), pyrogene und gefällte Kieselsäuren, Kieselgur, Aluminiumoxide, Aluminiumhydroxide, Talkum, Kaolin, Glimmer (Kalium-Aluminium-Silikat-Hydrat), Bariumsulfate wie natürlich vorkommendes Schwerspate und gefälltes Blanc Fix. Bevorzugt werden auch häufig Mischungen anorganischer Pigmente verwendet. Mischungen von organischen mit anorganischen Pigmenten werden ebenfalls häufig verwendet.Examples of suitable inorganic pigments are titanium dioxides, zinc sulfides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, manganese titanium rutiles, cobalt oxides, mixed oxides of cobalt and aluminum, rutile mixed phase pigments, rare earth sulfides, spinels of cobalt with nickel and zinc , Spinels based on iron and chromium with copper zinc as well as manganese, bismuth vanadate and extender pigments, in particular the Color Index Pigments Pigment Yellow 184, Pigment Yellow 53, Pigment Yellow 42, Pigment Yellow Brown 24, Pigment Red 101, Pigment Blue 28, Pigment Blue 36, Pigment Green 50, Pigment Green 17, Pigment Black 11, Pigment Black 33, and Pigment White 6; calcium carbonates also referred to as fillers such as naturally occurring chalk and precipitated calcium carbonate, dolomite, natural silica (fumed silica), fumed and precipitated silicas, kieselguhr, aluminum oxides, aluminum hydroxides, talc, kaolin, mica (potassium aluminum silicate hydrate), barium sulphates such as natural occurring barytes and felled blanc fix. Preference is also often given to using mixtures of inorganic pigments. Mixtures of organic and inorganic pigments are also commonly used.

Der Anteil der erfindungsgemäßen Dispersion an Weiß- oder Buntpigment liegt vorzugsweise bei 10 bis 80 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the inventive dispersion of white or colored pigment is preferably from 10 to 80% by weight, based on the weight of the dispersion.

Geeignete Netz- und Dispergiermittel sind vorzugsweise Polyacrylatsalze, Acrylat- und MSA-Copolymere, Alkylphenolethoxylate und Alkylphenolethoxylat-Ersatzstoffe, wie Guerbet-Derivate, Fettsäuer- und Fettalkoholderivate, insbesondere deren Alkoxylate, sowie EO/PO-Homo- und Copolymere und Polysiloxanether.Suitable wetting and dispersing agents are preferably polyacrylate salts, acrylate and MSA copolymers, alkylphenol ethoxylates and alkylphenol ethoxylate substitutes, such as Guerbet derivatives, fatty acid and fatty alcohol derivatives, in particular their alkoxylates, and also EO / PO homopolymers and copolymers and polysiloxane ethers.

Der Anteil der erfindungsgemäßen Dispersion an Netz- und Dispergiermitteln liegt vorzugsweise bei 0,01 bis 10 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the dispersion of the invention to wetting agents and dispersants is preferably from 0.01 to 10 wt .-%, based on the weight of the dispersion.

Geeignete Entschäumer sind vorzugsweise Mineralölentschäumer und deren Emulsionen, Siliconölentschäumer und Siliconölemulsionen, Polyalkylenglykole, Polyalkylenglykolfettsäureester, Fettsäuren, höherwertige Alkohole, Phosphorsäureester, hydrophob modifizierte Silika, Aluminiumtristearat, Polyethylenwachse und Amidwachse.Suitable defoamers are preferably mineral oil defoamers and their emulsions, silicone oil defoamers and silicone oil emulsions, polyalkylene glycols, polyalkylene glycol fatty acid esters, fatty acids, higher alcohols, phosphoric acid esters, hydrophobically modified silica, aluminum tristearate, polyethylene waxes and amide waxes.

Der Anteil der erfindungsgemäßen Dispersion an Entschäumer liegt vorzugsweise bei 0,01 bis 5 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the inventive dispersion of defoamer is preferably 0.01 to 5 wt .-%, based on the weight of the dispersion.

Geeignete Biozide zur Verhinderung der unkontrollierten Vermehrung von Bakterien, Algen und Pilzen sind Formaldehyd, Formaldehyd abspaltende Verbindungen, Methylisothiazolinon, Chlormethylisothiazolinon, Benzisothiazolinon, Bronopol, Dibromodicyanonbutan und silberchloridbeschichtetes Titandioxid.Suitable biocides for preventing the uncontrolled proliferation of bacteria, algae and fungi are formaldehyde, formaldehyde-releasing compounds, methylisothiazolinone, chloromethylisothiazolinone, benzisothiazolinone, bronopol, dibromodicyanone butane and silver chloride-coated titanium dioxide.

Der Anteil der erfindungsgemäßen Dispersion an Bioziden liegt vorzugsweise bei 0,01 bis 5 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the dispersion of the invention to biocides is preferably from 0.01 to 5 wt .-%, based on the weight of the dispersion.

Geeignete Alkalien sind anorganische Laugen von ein mehrwertigen Metallen, insbesondere Natronlauge und Kaliumlauge; ammoniakalische Lösungen sowie Amine, insbesondere Hydroxyamine wie Mono-, Di- und Triethanolamin, 2-Amino-2-methyl-1-propanol oder Butyldiethanolamin.Suitable alkalis are inorganic alkalis of a polyvalent metal, especially caustic soda and potassium hydroxide; ammoniacal solutions and amines, in particular hydroxyamines such as mono-, di- and triethanolamine, 2-amino-2-methyl-1-propanol or butyldiethanolamine.

Der Anteil der erfindungsgemäßen Dispersion an Alkalien liegt vorzugsweise bei 0,01 bis 5 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the dispersion of alkalis according to the invention is preferably from 0.01 to 5 wt .-%, based on the weight of the dispersion.

Geeignete Rheologieadditive als Mittel zur Regulierung der Viskosität sind z. B. Stärke- und Cellulosederivate und hydrophobmodifizierte ethoxylierte Urethane(HEUR)-Verdicker, alkaliquellbare Acrylatverdicker, hydrophob modifizierte Acrylatverdicker, Polymere der Acrylamidomethylpropansulfonsäure oder pyrogene Kieselsäure.Suitable rheology additives as viscosity modifiers are e.g. Starch and cellulose derivatives and hydrophobically modified ethoxylated urethanes (HEUR) thickeners, alkali-swellable acrylate thickeners, hydrophobically modified acrylate thickeners, polymers of acrylamidomethylpropanesulfonic acid or pyrogenic silica.

Der Anteil der erfindungsgemäßen Dispersion an Rheologieadditive liegt vorzugsweise bei 0,1 bis 10 Gew.-%, bezogen auf das Gewicht der Dispersion.The proportion of the dispersion of the invention to rheology additives is preferably from 0.1 to 10 wt .-%, based on the weight of the dispersion.

Eine Übersicht über gängige Hilfsstoffe geben Wernfried Heilen et al. in „Additive für wässrige Lacksysteme”, erschienen bei Vincentz Network, 2009 .Give an overview of common excipients Wernfried Heilen et al. in "Additives for Aqueous Lacquer Systems", published by Vincentz Network, 2009 ,

Eine besondere Eigenschaft der erfindungsgemäßen Dispersion ist ihr geringer VOC-Gehalt. A special property of the dispersion according to the invention is its low VOC content.

Die erfindungsmäßigen Dispersionen eignen sich zur Herstellung von Beschichtungen aller Arten. Besonders eignen sich die erfindungsmäßigen Dispersionen zur Herstellung von Anstrich- und Dispersionsfarben, Dispersionslacken und Haftklebstoffen.The dispersions of the invention are suitable for the production of coatings of all types. The novel dispersions are particularly suitable for the production of paints and dispersion paints, dispersion varnishes and pressure-sensitive adhesives.

Ein weiterer Gegenstand der Erfindung ist die Verwendung einer Verbindung der Formel (I) als Koaleszensmittel für die Herstellung von Beschichtungen wie Farben und Lacke, aber auch Klebstoffen.Another object of the invention is the use of a compound of formula (I) as a coalescing agent for the production of coatings such as paints and coatings, but also adhesives.

Ein besonders bevorzugtes Gebiet ist der Einsatz der Polyhydroxyfettsäureamid (I) als Koaleszensmittel für wässrige Dispersionsfarben. Die Verbindung (I) wird dazu vorzugsweise in Konzentrationen zwischen 0,1 bis 40 Gew.-% bezogen auf die Menge der Polymerteilchen eingesetzt in Abhängigkeit der gewünschten MFT des Polymers.A particularly preferred field is the use of the polyhydroxy fatty acid amide (I) as a coalescing agent for aqueous emulsion paints. For this purpose, the compound (I) is preferably used in concentrations of from 0.1 to 40% by weight, based on the amount of the polymer particles, depending on the desired MFT of the polymer.

In einer besonders bevorzugten Ausführung wird das Polyhydroxyfettsäureamid (I) in Konzentrationen von 2 bis 10 Gew.-% bezogen auf die Menge der Polymerteilchen eingesetzt.In a particularly preferred embodiment, the polyhydroxy fatty acid amide (I) is used in concentrations of from 2 to 10% by weight, based on the amount of the polymer particles.

Die erfindungsgemäße Dispersion enthält die Verbindung der Formel (I) vorzugsweise in Mengen von 0,01 bis 50 Gew.-%, insbesondere 0,02 bis 10 Gew.-%, bezoen auf das Gesamtgewicht der Dispersion.The dispersion according to the invention preferably contains the compound of the formula (I) in amounts of 0.01 to 50% by weight, in particular 0.02 to 10% by weight, based on the total weight of the dispersion.

Die erfindungsmäßigen Polyhydroxyfettsäureamide (I) können in reiner Form oder als Gemische untereinander eingesetzt werden.The polyhydroxy fatty acid amides (I) according to the invention can be used in pure form or as mixtures with one another.

BeispieleExamples

Prozentangaben in dieser Beschreibung sind Gewichtsprozente bezogen auf das Gewicht der Gesamtzusammensetzung, sofern nichts anderes angegeben ist.Percentages in this specification are percentages by weight based on the weight of the total composition unless otherwise specified.

Aufgabe der erfindungsmäßigen Koaleszensmittel ist die Absenkung der MFT von Polymerdispersionen auf ≤ 15°C, vorzugsweise auf ≤ 5°C. Die MFT wurde nach ASTM Methode D 2354 bestimmt. Dazu wurde eine 50%ige wässrige Styrol/Acrylat-Polymerdispersion (Mowilith® DM 611, Firma Celanese) mit entsalztem Wasser 1:1 verdünnt und mit 2–8 Gew.-% Koaleszensmittel bezogen auf die Feststoffmenge des Polymers versetzt. Diese Polymerdispersion wurde auf einer temperierten Platte mit Temperaturgradient ausgezogen und während der Trocknung beobachtet. An der Stelle, an der der Film gerade noch ohne Schädigungen austrocknet, wird als MFT dokumentiert.The object of the coalescents according to the invention is to lower the MFT of polymer dispersions to ≦ 15 ° C., preferably to ≦ 5 ° C. The MFT was after ASTM Method D 2354 certainly. For this, a 50% aqueous styrene / acrylate polymer dispersion (Mowilith ® DM 611, Celanese) with deionized water diluted 1: 1 and covered with 2-8 wt .-% coalescing agents are added to the solid amount of the polymer. This polymer dispersion was drawn out on a tempered plate with temperature gradient and observed during drying. At the point where the film just dries out without damage is documented as MFT.

Die erfindungsmäßigen Koaleszensmittel wurden gegenüber Koaleszensmitteln entsprechend dem Stand der Technik verwendet und sind in Tabelle 1 zusammengefasst.The present coalescents have been used over prior art coalescents and are summarized in Table 1.

N-C8/C10 Acyl-N-methyl-glucamin wurde als 50%-ige wässrige Lösung, N-C12/C18 Acyl-N-methyl-glucamin und N-Coco-acyl-N-methyl-glucamin wurden als 25%-ige wässrige Lösungen eingesetzt. Alle Konzentrationsangaben der erfindungsmäßigen Koaleszensmittel sind auf deren Aktivgehalt bezogen. Tabelle 1: Verwendete Koaleszensmittel Beispiel Koaleszensmittel Siedepunkt [°C] 1 (V) Vergleichsbeispiel Dipropylenglykolmonobutylether 231 2 (V) Vergleichsbeispiel Butyldiglykolacetat 248 3 (V) Vergleichsbeispiel Texanol 254 4 Erfindungsmäßiges Beispiel N-C8/C10 Acyl-N-methyl-glucamin (Glucamide 810, Firma Clariant) >> 250 5 Erfindungsmäßiges Beispiel N-C12/C18 Acyl-N-methyl-glucamin (Glucamide 1218, Firma Clariant) >> 250 6 Erfindungsmäßiges Beispiel N-Coco-acyl-N-methyl-glucamin (Glucamide CC, Firma Clariant) >> 250 NC 8 / C 10 acyl-N-methyl-glucamine was used as a 50% aqueous solution, NC 12 / C 18 acyl-N-methyl-glucamine and N-coco-acyl-N-methyl-glucamine were used as 25% ige aqueous solutions used. All concentration data of the coalescents according to the invention are based on their active content. Table 1: Coalescents used example coalescent Boiling point [° C] 1 (V) Comparative Example dipropylene 231 2 (V) Comparative Example butyldiglycolacetate 248 3 (V) Comparative Example Texanol 254 4 Inventive example NC 8 / C 10 acyl-N-methyl-glucamine (Glucamide 810, Clariant) >> 250 5 Inventive example NC 12 / C 18 acyl N-methyl-glucamine (glucamides 1218 Clariant) >> 250 6 Inventive example N-coco-acyl-N-methyl-glucamine (Glucamide CC, Clariant) >> 250

Die bestimmten Mindestfilmbildetemperaturen sind in Tabelle 2 zusammengefasst, Beispiel 7 entspricht der MFT des Bindemittels ohne Koaleszensmittel als Referenzwert. Wie die Beispiele 8 bis 25 zeigen, sind alle Koaleszensmittel in der Lage die MFT zu senken, so dass sie unterhalb von 15°C liegt; die erfindungsmäßigen Beispiele 4 und 6 senken die MFT auf eine Vorzugstemperatur ≤ 5°C. Gleichzeitig haben die erfindungsmäßigen Koaleszensmittel 4 bis 6 einen deutlich höheren Siedepunkt als die Vergleichsbeispiele 1 bis 3 nach dem Stand der Technik (Tabelle 1), was sich auf den VOC-Gehalt einer Dispersion auswirkt. Tabelle 2: Mindestfilmbildetemperaturen Beispiel Konzentration [Gew.-%] Koaleszensmittel [°C] 1 (V) 2 (V) 3 (V) 4 5 6 7 0 18,0 18,0 18,0 18,0 18,0 18,0 8–10 2,0 9,5 7,5 10,0 11–16 4,0 4,5 0 4,5 14,5 12,5 13,0 17–19 6,0 9 11 12 20–25 8,0 0 0 0 5 11,5 < 3 The determined minimum film forming temperatures are summarized in Table 2, Example 7 corresponds to the MFT of the binder without coalescing agent as the reference value. As shown in Examples 8-25, all coalescing agents are capable of lowering the MFT to be below 15 ° C; Inventive Examples 4 and 6 lower the MFT to a preferred temperature ≤ 5 ° C. At the same time, the coalescing agents 4 to 6 according to the invention have a significantly higher boiling point than the prior art comparative examples 1 to 3 (Table 1), which has an effect on the VOC content of a dispersion. Table 2: Minimum Filming Temperatures example Concentration [% by weight] Coalescing agent [° C] 1 (V) 2 (V) 3 (V) 4 5 6 7 0 18.0 18.0 18.0 18.0 18.0 18.0 8-10 2.0 9.5 7.5 10.0 11-16 4.0 4.5 0 4.5 14.5 12.5 13.0 17-19 6.0 9 11 12 20-25 8.0 0 0 0 5 11.5 <3

Zur Bestimmung der Eigenschaften der erfindugsmäßigen Koaleszensmittel in Dispersionsfarben, wurden die Koaleszensmittel in einer Dispersionsfarbe der folgenden Zusammensetzung (Tabelle 3) eingearbeitet. Tabelle 3: Zusammensetzung der Dispersionsfarbe. Nr. Komponente Funktion Gew.-% 1 Wasser 29,0 2 Ammonika-Lösung (25%-ig) Puffer 0,1 3 Calgon N Dispergiermittel 0,1 4 Bermocoll EHM 200 Verdicker 0,5 5 Koaleszensmittel Koaleszensmittel 1,5 6 Byk 038 Entschäumer 0,3 7 Mowiplus XW 330 Dispergiermittel 0,3 8 Nipacide BMS Biozid 0,2 9 Finntalc M 20 SL Pigment 8,0 10 Mica TF Pigment 8,0 11 Omyacarb 10 – AV Pigment 17,0 12 Omyacarb extra – CL Pigment 17,0 13 Kronos 2160 Pigment 4,0 14 Wasser 5,4 15 Mowilith DM 2452, 50% Binder 8,0 16 Tafigel PU 40 (1:9 in Wasser) Verdicker 0,3 17 Agitan 282 Entschäumer 0,3 Summe 100,0 PVK 84,3 Feststoffgehalt 58,0 To determine the properties of the coalescent compositions of the invention in emulsion paints, the coalescing agents were incorporated in an emulsion paint of the following composition (Table 3). Table 3: Composition of the emulsion paint. No. component function Wt .-% 1 water 29.0 2 Ammonia solution (25%) buffer 0.1 3 Calgon N dispersants 0.1 4 Bermocoll EHM 200 thickener 0.5 5 coalescent coalescent 1.5 6 Byk 038 defoamers 0.3 7 Mowiplus XW 330 dispersants 0.3 8th Nipacide BMS biocide 0.2 9 Finntalc M 20 SL pigment 8.0 10 Mica TF pigment 8.0 11 Omyacarb 10 - AV pigment 17.0 12 Omyacarb extra - CL pigment 17.0 13 Kronos 2160 pigment 4.0 14 water 5.4 15 Mowilith DM 2452, 50% binder 8.0 16 Tafigel PU 40 (1: 9 in water) thickener 0.3 17 Agitan 282 defoamers 0.3 total 100.0 PVK 84.3 Solids content 58.0

Zunächst wurden die Komponenten 1–8 vorgelegt und anschließend mit den Komponenten 9–13 unter hoher Scherrate zu einer Pigementdispersion dispergiert.First, components 1-8 were charged and then dispersed with high shear rate components 9-13 to a pigment dispersion.

Anschließend werden die Komponenten 14–17 unter Rühren (geringe Scherrate) zugegeben. Dabei wurden stets 1,5% Koaleszensmittel bezogen auf den Aktivgehalt zugegeben. Anschließend wurde die Viskosität, Lagerstabilität, die Gefriertaustabilität sowie der Nassabrieb bestimmt.Subsequently, components 14-17 are added with stirring (low shear rate). In this case, always 1.5% coalescents were added based on the active content. Subsequently, the viscosity, storage stability, freeze stability and wet abrasion were determined.

Die Viskosität wurde auf einem Haake Viscotester 550 von ThermoScientific bestimmt.The viscosity was determined on a Haake Viscotester 550 from ThermoScientific.

Zur Bestimmung der Lagerstabilität wurde die Viskosität nach einer Woche bei 60°C bestimmt.To determine the storage stability, the viscosity was determined after one week at 60 ° C.

Zur Bestimmung der Gefriertaustabilität wurde eine Probe der Farbe bei –18°C eingefroren und anschließend wieder aufgetaut. Dies wurde so lange wiederholt, wie keine dauerhaften Schäden zu erkennen waren. Beurteilt wurde die Anzahl der gefriertaustabilen Zyklen.To determine freeze stability, a sample of the color was frozen at -18 ° C and then thawed again. This was repeated as long as no permanent damage was detected. The number of freeze-stable cycles was evaluated.

Die Ergebnisse der Ausprüfungen der Dispersionsfarbe sind in Tabelle 4 zusammengefasst. Der bestimmte VOC-Gehalt zeigt, dass der VOC-Gehalt der fertigen Dispersionsfarben mit den erfindungsmäßigen Koaleszensmitteln (Beispiele 27 bis 29) unterhalb der Vorgaben der EU-Richtlinie 2004/42/EG liegt. Tabelle 4: Eigenschaften der Dispersionsfarben Beispiel Beschreibung Viskosität 1/60 s [mPas] Gefriertaustabile Zyklen VOC-Gehalt [%] Initial 1 Woche bei 60°C 26 (V) 0,5% Texanol +1,0% Dowanol DPnB 3017 3436 1 1,9 27 N-C8/C10 Acyl-N-methyl-glucamin 1541 1466 5 0,04 28 N-C12/C18 Acyl-N-methyl-glucamin 1034 1041 5 0,05 29 N-Coco-acyl-N-methyl-glucamin 603 561 5 0,07 The results of the tests of the emulsion paint are summarized in Table 4. The determined VOC content shows that the VOC content of the finished emulsion paints with the coalescents according to the invention (Examples 27 to 29) is below the specifications of the EU Directive 2004/42 / EC lies. Table 4: Properties of the emulsion paints example description Viscosity 1/60 s [mPas] Freeze-stable cycles VOC content [%] initial 1 week at 60 ° C 26 (V) 0.5% Texanol + 1.0% Dowanol DPnB 3017 3436 1 1.9 27 NC 8 / C 10 acyl-N-methyl-glucamine 1541 1466 5 0.04 28 NC 12 / C 18 acyl-N-methyl-glucamine 1034 1041 5 0.05 29 N-coco-acyl-N-methyl-glucamine 603 561 5 0.07

ZITATE ENTHALTEN IN DER BESCHREIBUNG QUOTES INCLUDE IN THE DESCRIPTION

Diese Liste der vom Anmelder aufgeführten Dokumente wurde automatisiert erzeugt und ist ausschließlich zur besseren Information des Lesers aufgenommen. Die Liste ist nicht Bestandteil der deutschen Patent- bzw. Gebrauchsmusteranmeldung. Das DPMA übernimmt keinerlei Haftung für etwaige Fehler oder Auslassungen.This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Zitierte PatentliteraturCited patent literature

  • WO 0179140 [0003] WO 0179140 [0003]
  • US 2218237 [0004] US 2218237 [0004]
  • US 3091632 [0005] US 3091632 [0005]
  • US 3312652 [0005] US 3,312,652 [0005]
  • US 5236987 [0006] US 5236987 [0006]
  • WO 2005/026249 [0006] WO 2005/026249 [0006]
  • DE 102010005973 [0007] DE 102010005973 [0007]
  • WO 2005049719 [0007] WO 2005049719 [0007]
  • US 8106239 [0008] US 8106239 [0008]
  • WO 2012069098 [0009] WO 2012069098 [0009]
  • DE 102007021139 [0009] DE 102007021139 [0009]
  • US 4435534 [0010] US 4435534 [0010]
  • US 2003/204003 [0010] US 2003/204003 [0010]
  • US 4525512 [0010] US 4525512 [0010]
  • WO 0056823 [0010] WO 0056823 [0010]
  • US 2002/061940 [0012] US 2002/061940 [0012]
  • WO 9412609 [0015] WO 9412609 [0015]
  • WO 9841601 [0016] WO 9841601 [0016]
  • WO 9523840 [0017] WO 9523840 [0017]
  • EP 0745719 [0018] EP 0745719 [0018]
  • DE 69811179 [0019] DE 69811179 [0019]
  • WO 2014/056561 [0020] WO 2014/056561 [0020]
  • DE 19934836 [0021] DE 19934836 [0021]
  • WO 9206071 [0022] WO 9206071 [0022]
  • WO 9206073 [0022] WO 9206073 [0022]
  • WO 9208687 [0022] WO 9208687 [0022]
  • DE 4322874 [0022] DE 4322874 [0022]

Zitierte Nicht-PatentliteraturCited non-patent literature

  • Wernfried Heilen et al. in „Additive für wässrige Lacksysteme”, erschienen bei Vincentz Network, 2009 [0047] Wernfried Heilen et al. in "Additives for Aqueous Lacquer Systems", published by Vincentz Network, 2009 [0047]
  • ASTM Methode D 2354 [0056] ASTM Method D 2354 [0056]
  • EU-Richtlinie 2004/42/EG [0066] EU Directive 2004/42 / EC [0066]

Claims (18)

Dispersion enthaltend (A) mindestens eine Verbindung der Formel (I)
Figure DE102014016763A1_0003
worin R1 für eine Kohlenwasserstoffgruppe mit 7 bis 21 Kohlenstoffatomen steht, (B) einen polymeren Binder und (C) Wasser.Dispersion comprising (A) at least one compound of the formula (I)
Figure DE102014016763A1_0003
wherein R 1 is a hydrocarbon group having 7 to 21 carbon atoms, (B) a polymeric binder and (C) water. Dispersion nach Anspruch 1, die darüber hinaus einen oder mehrere der Bestandteile ausgewählt aus der Gruppe bestehend aus Pigment, Dispergiermittel, Entschäumer, Alkali, Rheologie-Additiv, Biozid, Netzmittel enthält.The dispersion of claim 1, further comprising one or more of the ingredients selected from the group consisting of pigment, dispersant, defoamer, alkali, rheology additive, biocide, wetting agent. Dispersion nach Anspruch 1 und/oder 2, wobei R1 eine aliphatische Gruppe ist.Dispersion according to claim 1 and / or 2, wherein R 1 is an aliphatic group. Dispersion nach einem oder mehreren der Ansprüche 1 bis 3, worin 2 bis 6 verschiedene Verbindungen der Formel (I) zum Einsatz kommen.Dispersion according to one or more of claims 1 to 3, wherein 2 to 6 different compounds of formula (I) are used. Dispersion nach einem oder mehreren der Ansprüche 1 bis 4, bei der die Konzentration der Verbindung der Formel (I) 0,01 bis 50 Gew.-% beträgt.Dispersion according to one or more of Claims 1 to 4, in which the concentration of the compound of the formula (I) is from 0.01 to 50% by weight. Dispersion nach einem oder mehreren der Ansprüche 1 bis 4, bei der die Konzentration der Verbindung der Formel (I) 0,01 bis 10% beträgt.Dispersion according to one or more of Claims 1 to 4, in which the concentration of the compound of the formula (I) is from 0.01 to 10%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 6, enthaltend ein Weiß- oder Buntpigment in einer Menge von 10 bis 80 Gew.-%.Dispersion according to one or more of claims 1 to 6, containing a white or colored pigment in an amount of 10 to 80 wt .-%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 7, enthaltend Netz- oder Dispergiermittel in einer Menge von 0,01 bis 10 Gew.-%.Dispersion according to one or more of claims 1 to 7, containing wetting or dispersing agent in an amount of 0.01 to 10 wt .-%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 8, enthaltend Entschäumer in einer Menge von 0,01 bis 5 Gew.-%.Dispersion according to one or more of claims 1 to 8, comprising defoamer in an amount of 0.01 to 5 wt .-%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 9, enthaltend Biozide in einer Menge von 0,01 bis 5 Gew.-%.Dispersion according to one or more of claims 1 to 9, containing biocides in an amount of 0.01 to 5 wt .-%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 10, enthaltend Alkalien in einer Menge von 0,01 bis 5 Gew.-%.Dispersion according to one or more of claims 1 to 10, containing alkalis in an amount of 0.01 to 5 wt .-%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 11, enthaltend Rheologie-Additive einer Menge von 0,1 bis 10 Gew.-%.Dispersion according to one or more of claims 1 to 11, containing rheology additives in an amount of 0.1 to 10 wt .-%. Dispersion nach einem oder mehreren der Ansprüche 1 bis 12, worin 1 bis 80 Gew.-% des Bestandteils (B) enthalten sind.Dispersion according to one or more of claims 1 to 12, wherein 1 to 80 wt .-% of the component (B) are contained. Dispersion nach einem oder mehreren der Ansprüche 1 bis 13, worin 1 bis 80 Gew.-% Wasser enthalten sind.Dispersion according to one or more of claims 1 to 13, wherein 1 to 80 wt .-% water are included. Dispersion nach einem oder mehreren der Ansprüche 1 bis 14, worin die Verbindung der Formel (I) von Glukose abgeleitet ist.Dispersion according to one or more of claims 1 to 14, wherein the compound of formula (I) is derived from glucose. Verwendung einer Verbindung der Formel (I)
Figure DE102014016763A1_0004
worin R1 für eine lineare oder verzweigte, gesättigte oder ungesättigte Kohlenwasserstoffgruppe mit 7 bis 21 Kohlenstoffatomen steht, als Koaleszensmittel.Use of a compound of the formula (I)
Figure DE102014016763A1_0004
wherein R 1 is a linear or branched, saturated or unsaturated hydrocarbon group having 7 to 21 carbon atoms, as a coalescing agent. Verwendung nach Anspruch 17 worin R1 eine aliphatische Gruppe ist.Use according to claim 17 wherein R 1 is an aliphatic group. Verwendung nach Anspruch 17 und/oder 18 worin 2 bis 6 verschiedene Verbindungen der Formel (I) zum Einsatz kommen.Use according to claim 17 and / or 18 wherein 2 to 6 different compounds of formula (I) are used.
DE102014016763.1A 2014-11-13 2014-11-13 Low-VOC coalescents for aqueous dispersions Withdrawn DE102014016763A1 (en)

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