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
  • 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
• • 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
  • C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
  • C09D125/02—Homopolymers or copolymers of hydrocarbons
  • C09D125/04—Homopolymers or copolymers of styrene
  • C09D125/08—Copolymers of styrene
  • C09D125/14—Copolymers of styrene with unsaturated esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09D133/08—Homopolymers or copolymers of acrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09D133/10—Homopolymers or copolymers of methacrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • 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
• • 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
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/47—Levelling agents
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/10—Esters; Ether-esters
  • C08K5/101—Esters; Ether-esters of monocarboxylic acids

Definitions

• the invention relates to the use of esters of the general formula R 1 -COOR 2 , wherein R 1 is an alkyl radical having 9 to 23 C atoms and R 2 is a saturated alkyl radical selected from the group consisting of methyl, ethyl, n-propyl and i-propyl is, as a coalescing agent, in particular for the production of coating materials.
• Coalescing agents also called film-forming aids
• They are added to aqueous coating materials and cause a filming of the dispersed polymer particles to form a homogeneous paint film. Their addition is required if the film-forming temperature of the binder is above the application temperature.
• Known film-forming aids are: ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol butyl ether, ethylene glycol hexyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, diethylene glycol hexyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol phenyl ether, propylene glycol t-butyl ether, 2.
• coalescents have been used in substantial quantities in latex coatings, which are based in particular on small particles of synthetic plastics such as polyacrylates. These coalescing agents (also called filming aids) are added to the coatings to improve film formation. The function is based on the fact that the coalescing agent softens the latex particles so that they flow together and form a continuous film.
• This film has optimal film properties after the evaporation of the water.
• the so-called film-forming temperature is important, in which (or below) the polymer particles flow together to form a film.
• the usual coalescing agents lower the film forming temperature of the polymer.
• coalescing agents are certain esters and ethers;
• Known technical standards are the hydroxyester “Texanol” from Eastman (also often called TMB, a 2,2,4-trimethyl-1,3-pentanediol mono-isobutyrate) and "EGBE” from Union Carbide (ethylene glycol monobutyl ether).
• EP 069,839 B1 claims the use of hydroxy ester mixtures as leveling agents for aqueous polymer dispersions. They are those compounds which are accessible by reacting propylene oxide with aliphatic C 7 _i 2 monocarboxylic acids.
• US 2005/0182168 A1 discloses a combination of glycol esters of vegetable oil-based fatty acids and antioxidants. Propylene glycol monoesters are specifically thematized.
• Claim 1 of US Pat. No. 6,762,230 B2 is directed to coating compositions comprising a latex polymer and a coalescing agent of the formula R 1 (CO-X r -O) n -R 2 .
• R 1 is an organic group
• X is a divalent organic group
• the index r may be 0 or 1
• the index n may be in the range of 1 to 10
• R 2 is hydrogen or an organic group.
• r is the value 0 and n is 1 and the radicals R 1 and R 2 are alkyl radicals
• the abovementioned formula describes fatty acid esters. It should be noted, however, that fatty acid esters are not specifically disclosed in US Pat. No. 6,762,230 B2. On the contrary, the concrete coalescing agents of US Pat. No. 6,762,230 B2 are not fatty acid esters.
• esters of straight-chain C 2-6 fatty acids where the alcohol component of the esters is aliphatic C 3-4 -alcohols, as solvent for paints. Coalescing agents are not mentioned here.
• coalescing agents are particularly suitable for the production of coatings such as paints, paints and the like, but also for adhesives.
• a particularly preferred field for the use of coalescing agents to be provided are the so-called emulsion paints.
• coalescing agent also referred to in the literature as filming assistant or film-forming assistant
• filming assistant also referred to in the literature as filming assistant or film-forming assistant
• coalescing agents to be developed according to the invention are intended in particular for use in aqueous dispersions of plastics or latex particles which are suitable for coating purposes of any kind (for example for water-based paints and coatings).
• Such dispersions which are typically prepared by emulsion polymerization and which, in addition to water, the auxiliaries used in the emulsion polymerization and the plastic or latex particles, may contain further constituents which are customarily used for the particular desired coating purpose, are usually applied to the coating to be coated Surface applied, then followed by evaporation of the water and finally it is essential that the Polymer standing. Latex particles flow into each other and form a homogeneous film.
• This process of film formation presupposes that a minimum temperature is maintained, which is called minimum film forming temperature (MFT) by a person skilled in the art. For example, if the MFT of a system is 20 ° C., it means that film formation is successful only when the temperature is 20 ° C.
• MFT minimum film forming temperature
• the present invention has the aim of developing coalescing agents which are as effective as possible in lowering the MFT of aqueous dispersions of plastic or latex particles intended for any desired coating purposes.
• the invention relates to the use of esters of the general formula (I)
• R 1 is an alkyl radical having 9 to 23 C atoms and
• R 2 is a saturated alkyl radical selected from the group of methyl, ethyl, n-propyl and i-propyl as a coalescing agent.
• the radical R 1 may be linear or branched, saturated or simply olefinically unsaturated.
• the radical R 1 is a saturated alkyl radical.
• esters of the formula (I) are preferably suitable for the production of coatings such as paints, coatings and the like, but also for adhesives.
• the esters of the formula (I) are used as coalescing agents in the preparation of coatings of any type based on aqueous polymer dispersions or latex dispersions.
• esters (I) as coalescing agents are the so-called (water-based) emulsion paints.
• esters (I) examples include:
• Decanoic acid (capric acid), undecanoic acid, dodecanoic acid (lauric acid), tridecanoic acid, tetradecanoic acid (myristic acid), pentadecanoic acid, hexadecanoic acid (palmitic acid), heptadecanoic acid and octadecanoic acid (stearic acid), isostearic acid, nonadecanoic acid, eicosanoic acid (arachic acid), dodecanoic acid (behenic acid ).
• These fatty acids are among the saturated fatty acids. They are used in the context of the present invention preferably as acid components of the ester (I).
• esters (I) are derived, as far as the acid component is concerned, preferably from fatty acids having 10 to 18 carbon atoms. These may be linear or branched, saturated or simply olefinically unsaturated. Fatty acids of native origin are preferred. In one embodiment, the esters (I), as far as the acid component is concerned, are derived from linear, monoolefinically unsaturated fatty acids.
• esters (I), as far as the acid component is concerned are derived from branched, saturated fatty acids.
• esters (I), as far as the acid component is concerned, are derived from linear, saturated fatty acids.
• esters (I) in the context of the present invention are methyl esters, ie compounds which are characterized by the general formula (Ia)
• R 1 is a saturated alkyl radical having 9 to 18 carbon atoms.
• Methyl lauric acid, methyl myristate and methyl palmitate or mixtures thereof are very particularly preferred.
• esters (I) in the context of the present invention are isopropyl esters, ie compounds which are characterized by the general formula (I-b)
• R 1 is a saturated alkyl radical having 9 to 18 carbon atoms.
• esters (I) are very efficient as coalescing agents, as can be seen from the fact that they are quite capable of lowering the minimum film-forming temperature (MFT) of aqueous polymer dispersions.
• coatings (films) which are obtainable using aqueous polymer dispersions containing the esters (I) to be used according to the invention are generally much harder after four weeks of storage and thus more robust and less susceptible to soiling than those prepared with commercially available coalescing agents .
• Another advantage of the present invention to be used ester (I) is that their boiling point above 250 0 C. which is classified as "VOC-free" according to EU regulations 1999/42 / EC and 2004/42.
• esters (I) are structurally close to them and / or in comparison to commercial hydroxyester-based coalescing agents.
• the Applicant has found that methyl lauric acid and isopropyl acrylate have a lower tendency to hydrolysis in an aqueous-alkaline medium than butyl laurate and the commercial 2,2,4-trimethyl-1,3-pentanediol mono-isobutyrate (TMB).
• TMB 2,2,4-trimethyl-1,3-pentanediol mono-isobutyrate
• esters (I) to be used according to the invention can be used in pure form or in the form of mixtures with one another. If desired, the esters (I) may also be used in combination with known coalescing agents.
• Another object of the invention is therefore the use of compositions containing
• esters (I) - compounds selected from the group of esters, ethers and hydroxy esters as coalescing agents in particular in the preparation of coatings of any kind based on aqueous polymer or latex dispersions, and preferably in the production of coatings based on emulsion paints.
• the esters (I) to be used according to the invention come in particular as coalescing agents for aqueous dispersions of polymer to be polymerized. Latex particles are used. This applies both when the esters (I) are used alone (in the form a pure species or a mixture of different species) or in admixture with other - different - coalescing agents.
• esters (I) are preferably (depending on the MFT of the polymer) in amounts of 0.1 to 40 wt .-% and in particular 2 to 6 wt .-% - based on the amount of polymer or latex particles whose minimum film-forming temperature should be lowered - used.
• esters (I) are preferably used (depending on the MFT of the polymer) in amounts of from 0.1 to 5% by weight and in particular from 0.5 to 2% by weight, based on the total coating formulation.
• esters (I) can vary the amount of esters (I) according to the composition of a specific dispersion or a specific coating formulation and, if required, also use higher amounts of esters (I), especially if the system contains polymers with a high minimum film-forming temperature and / or a reduction to the lowest possible MFT values.
• aqueous dispersions may contain further additives and additives known to those skilled in the art, depending on the desired application or the type of coating.
• esters (I) according to the invention can be added to the aqueous dispersions immediately after the preparation, which is preferably carried out by emulsion polymerization, but also at a later time, for example during the preparation of a coating substance.
• the aqueous dispersions containing esters (I) to be used according to the invention can in principle be applied to any desired surfaces, for example wood, metal, plastic, glass, paper, concrete, masonry and plasters.
• Mowilith LDM 7451 Aqueous polymer dispersion based on acrylic acid ester / methacrylic ester / styrene (from Celanese)
• Acronal 290D Aqueous polymer dispersion based on butyl acrylate / styrene
• Acronal S 790 Aqueous polymer dispersion based on butyl acrylate / styrene
• Lipaton AE 4620 Aqueous polymer dispersion based on styrene / acrylic acid ester
• Mowilith DM 611 Aqueous polymer dispersion based on styrene / acrylic acid ester
• Rhoplex SG 30 Aqueous polymer dispersion based on acrylic acid ester (Fa.
• TMB Vl 2,2,4-trimethyl-1,3-pentanediol mono-isobutyrate
• % Bl or VI the amount of coalescing agent added to the aqueous polymer dispersion is given in% by weight, based on the polymer dispersions (in the form as supplied by the manufacturer).
• ester Bl has advantages in several respects over one of the industrial standards, namely VI, on:

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Dispersion Chemistry (AREA)
• Paints Or Removers (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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• 2007
  • 2007-05-03 DE DE102007021139A patent/DE102007021139A1/de not_active Withdrawn
• 2008
  • 2008-04-24 WO PCT/EP2008/003294 patent/WO2008135170A1/de not_active Ceased
  • 2008-04-24 JP JP2010506819A patent/JP5487098B2/ja not_active Expired - Fee Related
  • 2008-04-24 EP EP08749093A patent/EP2142606B1/de active Active
  • 2008-04-24 ES ES08749093T patent/ES2376605T3/es active Active
  • 2008-04-24 US US12/598,505 patent/US20100126384A1/en not_active Abandoned
  • 2008-04-24 CN CN2008800145874A patent/CN101675124B/zh active Active
  • 2008-04-24 AT AT08749093T patent/ATE531769T1/de active
• 2016
  • 2016-08-05 US US15/230,126 patent/US10533108B2/en active Active
• 2020
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