WO2013100836A1 - Alkyd resin composition comprising silica - Google Patents
Alkyd resin composition comprising silica Download PDFInfo
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- WO2013100836A1 WO2013100836A1 PCT/SE2012/000209 SE2012000209W WO2013100836A1 WO 2013100836 A1 WO2013100836 A1 WO 2013100836A1 SE 2012000209 W SE2012000209 W SE 2012000209W WO 2013100836 A1 WO2013100836 A1 WO 2013100836A1
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
Definitions
- the present invention relates to an alkyd resin composition
- an alkyd resin composition comprising at least one autoxidatively drying alkyd resin and at least one silica comprising silica nanoparticles. Said silica particles are incorporated into the oil phase of said alkyd resin.
- the present invention refers a method of obtaining said composition and to the use of said composition in coating formulations.
- Alkyd and other polyester resins are well known in the art and frequently and are typically used in a large number of applications, such as putties, lacquers, enamels, gel coats, powder coatings, coil coatings, polyurethane coatings and other coating systems, printing inks, synthetic lubricants, plasticizers, fibres, dental materials, adhesives, packagings and moulding compositions.
- Alkyd resins are polyesters which have been modified by the addition of for instance fatty acids or corresponding triglycerides.
- the term "alkyd” or “alkyd resin” was coined to define the reaction product of polyalcohols and polycarboxylic acids, in other words, polyesters. However, its definition has been narrowed to include only those polyesters comprising, in addition to polyalcohols and polycarboxylic acids, monobasic acids, usually long-chain fatty acids, or corresponding triglycerides.
- Oil-based alkyd resins are polyesters which have been modified by addition of saturated or unsaturated fatty acids or corresponding triglycerides.
- Alkyd resins comprising monocarboxylic acids, such as benzoic acid and/or other monocarboxylic acid not typically classified as fatty acid are by some manufacturers and alkyd technicians designated as oil-free alkyd resins.
- an alkyd resin can be designed to meet the property requirements.
- the main reactions involved in alkyd resin synthesis are polycondensations by esterification and ester interchange/transesterification.
- Alkyd resins are usually referred to by a brief description based on certain classification schemes. From the classification the general properties of the resin become immediately apparent to those having basic skills in the art.
- Alkyd resins can broadly be classified into drying and non-drying types depending on the ability of their films to dry by air oxidation, so called autoxidative drying. Air drying ability is derived from polyunsaturated fatty acids and/or triglycerides in the resin composition. If drying oils or fatty acids, such as linseed oil, are the sources of the fatty acids for the alkyd, the resin belongs to the drying type and is usually used as the film former of coatings or inks.
- the resin is a non-drying, physically or industrially drying or a curing/baking alkyd.
- the oil length is defined as the weight percent of oil or triglyceride equivalent.
- alkyd resins are well known in the art and do not require any further and over extensively detailed description. Said product is thoroughly disclosed and discussed in a number of chemicals encyclopaedias and handbooks, such as Kirk-Othmer, Encyclopedia of Chemical Technology, Modern Polyesters, Chemistry and Technology of Polyesters and Copolyesters, ed. by John Scheirs and Timothy E. Long, 2003, John Wiley & Sons Ltd, and Alkyd Resin Technology, Formulating Techniques and Allied Calculations, by T.C. Patton, Interscience Publishers, 1962.
- Polycarboxylic acids used in alkyd syntheses include aliphatic, cycloaliphatic or aromatic polycarboxylic acids and corresponding anhydrides, alkyl esters and halides, such as but not limited to o-phthalic acid or anhydride, isophthalic acid, terephthalic acid, 1 ,2-cyclohexanedicarboxylic acid or anhydride, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, tetrahydrophthalic acid or anhydride, hexahydrophthalic acid or anhydride, maleic anhydride, fumaric acid, adipic acid, azelaic acid, succinic acid or anhydride, sebacic acid, furandicarboxylic acids, tetrahydrofurandicarboxylic acids, trimelletic acid or anhydride, itaconic acid, citraconic acid and/or pyromelletic acid or an
- Polyalcohols used in alkyd syntheses include, but is not limited to, linear or branched aliphatic, cycloaliphatic or aromatic polyalcohols, polyester polyalcohols and polyether polyalcohols, such as but not limited to alkylene glycols, poly(alkylene) glycols, polycarbonate polyols, dihydroxyalkyl- 1 ,3-dioxanes, di(hydroxyalkyl)furans, di(hydroxyalkyl)tetrahydrofurans, 2-alkyl-l ,3 -propanediols, 2,2-dialkyl- 1 ,3-propanediols, 2-hydroxyalkyl- 1 ,3 -propanediols, 2,2-dihydroxyalkyl-l,3-propanediols, 2-alkyl-2-hydroxyalkyl-l,3-propanediols, as well as polyalkoxylated, such as
- polyalcohols include dendritic polyester and/or polyether polyalcohols.
- Said polyalcohols can suitably exemplified by ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1 ,4-butylene glycol, 1,3-butylene glycol, neopentyl glycol, 2-butyl-2-ethyl- 1,3-propanediol, 5,5-dihydroxymethyl-l,3-dioxane, di(hydroxymethyl)furan, di(hydroxymethyl)tetrahydrofuran, pentaerythritol spiroglycol (2,4,8, 10-tetraoxaspiro[5.5]undecane-3,9-diethanol), isosorbide, isomannide, isoidide, glycerol, di-glycerol, trimethylolethane, trimethylolpropane, trimethylolbutane, di
- Monocarboxylic acids and/or triglycerides used in alkyd syntheses suitably and preferably include abietic acid, benzoic acid, p-tert.-butylbenzoic acid, caproic acid, capric acid, castor fatty acid or castor oil, coconut fatty acid or coconut oil, cottonseed fatty acid or cottonseed oil, acrylic acid, methacrylic acid, crotonic acid, iso-crotonic acid, 2-ethylhexanoic acid, 2-propylheptanoic acid, lauric acid, linoleic acid, oleic acid, pelargonic acid, soybean fatty acid or soybean oil, tall oil fatty acid, safflower fatty acid or safflower oil, linseed fatty acid or linseed oil, sunflower fatty acid or sunflower oil, linolenic acid, eleostearic acid, tung oil, poppy seed oil, perilla oil, oiticia oil,
- hydroxyfunctional carboxylic acids such as but not limited to, dimethylolpropionic acid, dimethylolbutyric acid, trihydroxymethylacetic acid, dihydroxymethylvaleric acid, dihydroxypropionic acid, heptonic acid, citric acid, tartaric acid, dihydroxymalonic acid, gluconic acid, dihydroxybenzoic acid, hydroxyvaleric acid, hydroxypropionic acid and/or hydroxypivalic acid and/or lactones and other inner ether, such as glycolide, valerolactone, propiolactone, caprolactone and/or polycaprolactone.
- hydroxyfunctional carboxylic acids such as but not limited to, dimethylolpropionic acid, dimethylolbutyric acid, trihydroxymethylacetic acid, dihydroxymethylvaleric acid, dihydroxypropionic acid, heptonic acid, citric acid, tartaric acid, dihydroxymalonic acid, gluconic acid, dihydroxybenzoic acid, hydroxyvaleric acid, hydroxypropionic
- Alkyd resins can furthermore comprise linear or branched aliphatic, cycloaliphatic or aromatic monofunctional alcohols, such as alkanols having for instance 1-18 carbon atoms, 5-alkyl-5-hydroxyalkyl-l,3-dioxanes and/or monohydroxy functional (meth)allyl ethers.
- alkanols having for instance 1-18 carbon atoms
- 5-alkyl-5-hydroxyalkyl-l,3-dioxanes and/or monohydroxy functional (meth)allyl ethers.
- These compounds can suitably be exemplified by, but are not limited to, 2-ethylhexanol, 2-propylheptanol, isononanol, isodecanol, 5-methyl-5-hydroxymethyl-l,3-dioxane, 5-ethyl-5-hydroxymethyl-l,3-dioxane, glycerol di(meth)allyl ether, trimethylolethane di(meth)allyl ether, trimethylolpropane di(meth)allyl ether, trimethylolbutane di(meth)allyl ether and pentaerythritol tri(meth)allyl ether.
- alkyd resins can furthermore comprise isocyanate components comprising isocyanates and polyisocyanates, such as, but not limited to, methyl isocyanate, toluene diisocyanate, diphenyl methane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylene diisocyanate, dicyclohexyl methane diisocyanate, furan diisocyanate, tetrahydrofuran diisocyanate, cyclohexylene diisocyanate, xylene diisocyanate, naphthalene diisocyanate, phenylene diisocyanate, nonane triisocyanate and/or triphenyl methane triisocyanate.
- isocyanate based components include isocyanurates, biurets and allophanates.
- epoxy functional compounds such as, but not limited to, l ,2-epoxy-3-allyloxypropane, l-allyloxy-2,3-epoxypropane, l,2-epoxy-3-phenoxypropane, 1 -glycidyloxy-2-ethylhexane, bisphenol A-diglycidyl ether or a reaction product thereof, diglycidyl ether of pentaerythritol spiroglycol (glycidyl ether of 2,4,8, 10-tetraoxaspiro[5.5]undecane-3,9-diethanol), diglycidyl terephthalate, epoxidised soybean fatty acid, epoxidised soybean oil, epoxidised polyvinyl alcohol, epoxidised dehydrated castor oil, epoxidised linseed oil and 3,4-epoxy- -cyclohexylmethyl-3,4-
- Alkyd resins can furthermore be modified by compounds such as thiols, polythiols, thio acids, polythio acids, amines, polyamines, vinylics, such as styrene and vinyltoluene, silicones, oxetanes and/or hydroxyoxetanes, such as oxetanes of 2-alkyl-l ,3-propanediols, 2,2-dialkyl- 1 ,3-propanediols, 2-alkyl-2-hydroxyalkyl- 1 ,3-propanediols, 2,2-dihydroxyalkyl- -1,3-propanediols as well as dimers and polymers thereof.
- compounds such as thiols, polythiols, thio acids, polythio acids, amines, polyamines, vinylics, such as styrene and vinyltoluene, silicones, oxe
- Autoxidatively drying alkyd based compositions typically comprises one or more metallic driers, also known as siccatives, being metallic carboxylates, soaps, and resinates of for instance alkaline earth metals, rare earth metals or transition metals and monobasic carboxylic acids, such as 2-ethylhexanoic acid (octanoic acid), naphthenic acid, neodecanoic acid, stearic acid or other preferably lipophilic carboxylic acid.
- metallic driers also known as siccatives
- metallic carboxylates such as 2-ethylhexanoic acid (octanoic acid), naphthenic acid, neodecanoic acid, stearic acid or other preferably lipophilic carboxylic acid.
- driers typically used driers include primary driers, such as carboxylates and resinates of for instance cobalt, manganese, vanadium, iron and cerium and secondary driers, such as carboxylates and resinates of for instance lead, zirconium, aluminium, bismuth, strontium and barium.
- primary driers such as carboxylates and resinates of for instance cobalt, manganese, vanadium, iron and cerium
- secondary driers such as carboxylates and resinates of for instance lead, zirconium, aluminium, bismuth, strontium and barium.
- metallic driers include carboxylates and resinates of for instance calcium, zinc, lithium, lanthanium, neodynium, copper, titanium, nickel, tin and potassium.
- nanoparticles into coatings have been known for more than 10 years. The main focus has been to enhance the scratch resistance of ultraviolet (UV) curing coatings and waterborne coatings, such as two component polyurethane resins (2K PUR) clear coats to automotive and polyurethane dispersions (PUD) for flooring. Later nanoparticles have also been used to improve weather resistance and to reduce dirt pickup.
- UV ultraviolet
- nanoparticles include among others silica, titanium dioxide and cerium oxide.
- the properties of a material may change dramatically when it is in the form of very small particles of nano size.
- One parameter that increases is the surface area. Colloidal silica have for example a surface area in the range of 30-1000 m 2 /g.
- silica nanoparticles in alkyd resins is today to add a silica sol to a waterborne alkyd. This will give silica particles in the water phase and between the coalesced oil droplets. Upon drying/curing the silica particles will be located at the interface, that is between the surface exposed to air and the substrate. The silica particles will hence be unevenly distributed in the dried film. It has therefore been desirable to find a way to prepare improved compositions comprising alkyd resin and silica particles.
- An alkyd resin based coating composition and a process for obtaining a said composition has now been developed making it possible to transfer silica particles, such as silica nanoparticles, from having water as the outer phase to having alkyd as the outer phase.
- An alkyd resin as substantially 100% or only comprising possible residual azeotropic solvent used and/or esterification water formed in the alkyd process, is when the synthesis is completed cooled to for instance 30-140°C, such as 50-100°C, or alternatively a pre-produced alkyd resin, likewise as substantially 100%, is if not liquid at ambient temperature and/or necessary with regard to the viscosity, such as obtaining a viscosity of less than 30000-40000 mPas, heated to a temperature, such as a said temperature, liquefying the alkyd resin.
- silica in form of an aqueous sol is admixed into the alkyd resin.
- Silica is advantageously admixed at a low or moderate addition rate and under vigorous stirring.
- a suitable addition rate can be for instance 1-5, such as 2-3, parts per minute and per 100 parts of alkyd.
- the amount of silica calculated as 100% silica on 100% alkyd is suitably 0.1-10%, such as 0.1-6%, 0.5-5% or 0.5-4%, by weight.
- the alkyd resin or the alkyd/silica composition can, furthermore, optionally be neutralised with an inorganic compound or with ammonia or an organic amine.
- the neutralisation can be a partial or a full neutralisation, 100%, of unreacted acid groups (acid value).
- Alkyd resins used in the composition according to the present invention are suitably selected among short, medium, long and very long oil oxidatively drying alkyds having for instance an acid value of 5-20 mg KOH/g and being based on raw materials as disclosed previously. Alkyd resins having lower or higher acid values can of course also be used.
- Suitable inorganic compounds can be exemplified by sodium hydroxide, lithium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate.
- Suitable amines can be triethylamine, diethanolmethylamine.
- a surface active agent such as a surfactant may also be added to the alkyd resin and/or the alkyd/silica composition.
- the alkyd and/or the silica sol may also be slightly diluted, in an amount of for instance 1-5% by weight calculated on said alkyd or said silica sol, before, after or during said silica addition, with a solvent, for example propanol, butanol, pentanol, hexanol, octanol or the like.
- yielded alkyd/silica comprising composition can be stirred for some time and/or evaporated, for instance under vacuum or otherwise reduced pressure, to remove water, any residual azeotropic solvent and/or any other added volatile component.
- the temperature may here be raised to for instance 30-140°C, such as 50-100°C, and preferably not exceeding 150-160°C.
- Yielded mixture can, with or without said evaporation be diluted with an organic solvent, such as white spirit, xylene, butyl acetate, or be water emulsified, using conventional and known in the art additives and procedures, to yield an alkyd emulsion.
- Silica nanoparticles are normally in the form of sols or so called colloidal particles in water, which are almost monodisperse. Colloidal silica may comprise or consist of nanoparticles, while a nanosilica not necessarily is colloidal. Preferably, the silica nanoparticles used in the present composition is an aqueous silica sol. In some embodiment, the particles may have an average particle diameter ranging from about 2 to 150 nm, for example from about 3 to 60 nm, such as from about 5 to 40 nm, for example from about 5 to about 25 nm, for example from about 5 to about 12 nm.
- said silica is a sterically or electrostatically stabilised silica and/or is salt free and/or counter ion purified.
- Said silica is preferably and advantageously a siloxane, silazane or preferably silane modified or treated silica and/or is modified or treated yielding a silica having at least one epoxy and/or vinyl group.
- said silica is bonded to a monomelic, oligomeric or polymeric glycidoxysilane, glycidoxyalkylsilane, glycidoxyalkylalkoxysilane, cycloalkylepoxysilane, (meth)acryloxy- silane, (meth)acryloxyalkylsilane and/or (meth)acryloxyalkylalkoxysilane.
- the silica nanoparticles can for instance be anionic with sodium or ammonium stabilisation or silane modified anionic with sodium stabilisation, anionic with aluminate modification at the surface with sodium stabilisation, cationic with chloride stabilisation or sterically stabilised by for instance modification with silanes, ionic and/or non-ionic surfactants, including polymeric surfactants such as block-copolymers.
- the silica nanoparticles may be sterically or electrostatically stabilised.
- Silanes used to modify the particle surface can have different functional groups, such as thiol, amine or oxirane, for instance glycidoxy silanes and cycloaliphatic epoxysilanes. In the case of oxirane, it is normally ring opened during the modification to yield two hydroxyl groups instead.
- Embodiments of preferred and suitable silica compounds can be exemplified by, but not limited to, silica bonded to a monomeric, oligomeric or polymeric glycidoxysilane, glycidoxypropylsilane, tris-(trimethoxy)silane, octyltriethoxysilane, methyltriethoxysilane, methyltrimethoxysilane, tris-[3-(trimethoxysilyl)propyl]isocyanuratesilane, ⁇ -mercaptopropyl- trimethoxysilane, ⁇ -(S-ftriethoxysilylJpropy polysulfide, ⁇ -(3,4— epoxycyclohexyl)ethyl- trimethoxysilane; ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxy- silane, (3-glycidoxypropyl)
- the alkyd resin and/or the silica sol may in embodiments of the present composition be diluted with at least one organic solvent, such as propanol, butanol, pentanol, hexanol and/or octanol, in an amount of 1-5% by weight calculated on said alkyd or said silica sol.
- Said solvent can be added before, after or during said silica addition.
- Driers such as Zr, Fe, K, Cu, Mn and other drier additives known and used in the art, and/or curing agents, likewise known and used in the art, as well as a substantially reduced amount of cobalt based driers, such as at most 0.01% Co calculated on 100% alkyd, can of course in embodiments of the present invention be added to the composition of the present invention comprising silica particles, incorporated as substantially herein disclosed.
- the presence of silica particles in accordance with embodiments of the present invention, implies formulation of oxidatively drying coating systems being free of cobalt driers, which are on the verge of being faced out due to environmental and health issues, or only comprising substantially reduced amounts thereof.
- the composition of the present invention facilitates replacement of cobalt driers by manganese or iron driers and implies a substantial reduction of used amounts of manganese or iron based replacement driers.
- the advantages of having the silica particles in the alkyd phase are an improved drying without or with considerably reduced amounts of driers, such as cobalt octoate or naphthenate and/or other driers known in the art and/or previously herein discussed, improved dirt pickup resistance, improved adhesion, improved exterior durability, improved hardness, improved abrasion over time, less brittleness, improved hiding power and improved toughness.
- driers such as cobalt octoate or naphthenate and/or other driers known in the art and/or previously herein discussed
- the present invention also encompasses a method of obtaining a composition, as disclosed above, according to the invention, said method comprises admixing said aqueous silica sol into a substantially 100% alkyd resin being in a liquid state either at ambient temperature or at an elevated temperature, said silica sol being added in an amount of 0.1-10% such as 0.1-6%, 0.5-5% or 0.5-4%, by weight calculated as 100% silica on 100% alkyd resin.
- said silica is admixed under vigorous stirring.
- said method comprises an evaporation step, which can be performed under vacuum or reduced pressure, for example, and at a temperature 40-120°C, such as 80-100°C.
- the alkyd and/or said silica sol can be diluted with at least one organic solvent in an amount of 1-5% by weight calculated on said alkyd or said silica sol.
- suitable solvent include propanol, butanol, pentanol, hexanol and/or octanol.
- Said method can additionally comprise a neutralisation step wherein an inorganic base, ammonia and/or an amine is added.
- Said method can additionally comprise addition of at least one surfactant or emulsifier.
- Alkyd emulsions based on the composition of the present invention, which composition is obtained by the method disclosed above, can be manufactured by a variety of different methods. Depending on the properties of the alkyds, such as viscosity, acid value and hydroxyl value, some methods are preferred before others. Despite the choice of emulsion technology/process the outcome is dispersed alkyd droplets in a water phase, wherein the water is the continues media of the system. In order to achieve the alkyd droplets in the water phase and keep the system stable surfactants are typically used.
- a combination of two or more different surfactants may be used, such as a combination of one ionic (small molecule that possesses high diffusion) for promoting the droplet formation and one nonionic (large polymeric surfactant) for stabilising the droplets on a long term perspective.
- the properties of the surfactants (HLB value) and concentration, typically 1 to 10% surfactants on the solid alkyd, of the surfactant(s) can vary depending on the properties of the alkyd.
- the alkyd may be partially or fully neutralised in order to increase the compatibility with the surfactants. By neutralisation the differences in hydrophilicity and hydrophobicity between the two material is changed (reduced) and better presumption for more effective emulsifiers are obtained.
- the mixing device can be for instance a dissolver, specially designed stirrer, rotor-stator homogenisator or high pressure homogenisator.
- a typical solid content of an alkyd emulsion is from 30-60%.
- the present invention refers to the use of an alkyd resin composition as herein disclosed in production of materials and articles, such as decorative and/or protective solvent borne or waterborne varnishes, paints and enamels.
- Alkyds comprising, in accordance with the present invention, silica particles can be used for clear lacquers and for paints and enamels comprising pigments, fillers and any other type of additives commonly used and known in the art.
- Example 1 refer to utilised alkyd resins
- Examples 2-12 to embodiments of the composition according to the present invention
- Examples 13 and 14 are comparative examples without silica nanoparticles.
- drying times were assessed using a Beck-Koller Drying Recorder (Sheen Instruments Ltd).
- the test composition was applied on a glass plate using a draw bar yielding a wet coating having a filmthickness of 75 ⁇ 5 ⁇ . Drying was recorded according to ASTM D 5895.
- the amount of Co drier in embodiment Examples 5-8 are six (6) times lower than in comparative Example 14, which Example comprises an, in air drying alkyd resins, typically used amount of Co. Examples 5-8 thus evidences that a substantially reduced amount of Co with kept drying properties can be used in accordance with the present invention.
- alkyd emulsions were, using conventional methods as previously disclosed, prepared by emulsifying 40 parts by weight of a composition yielded in Example 2-14, with an addition of 2% by weight of an anionic surfactant and 8% by weight of a non-ionic surfactant (said percentages being weight percentages calculated on 100%> alkyd), in 60 parts by weight of water. All yielded emulsions were clear and stable. Used alkyd resins exhibited following properties:
- Alkyd Resin 1 Alkyd Resin 2
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80°C and 2.29 parts by weight of a 25% solution of NaOH were under stirring (210 rpm) added. The mixture was subsequently for 1 hour vigorously stirred (ca. 260 rpm). 6.67 parts by weight of an aqueous silica sol (Bindzil ® PC300, Eka Nobel, Sweden) was now added and the resulting mixture was for 1 hour vigorously stirred (ca. 260 rpm) at 80°C. Yielded composition was finally submitted to vacuum at 80°C during 2 hours to remove water and/or residual azeotropic solvent. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in Table 1.
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80°C. 6.67 parts by weight of an aqueous silica sol (Bindzil ® PC300, Eka Nobel, Sweden) and 2 parts of butanol were added under vigorous stirring (ca. 260 rpm). Yielded composition was for 1 hour vigorously stirred (ca. 260 rpm) at 80°C and yielded composition was finally submitted to vacuum at 80°C during 2 hours to remove water. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80°C and 2.29 parts by weight of a 25% solution of NaOH were under stirring (210 rpm) added. The mixture was for 1 hour vigorously stirred (ca. 260 rpm). 6.67 parts by weight of a silica sol (Bindzil ® PC300, Eka Nobel, Sweden) and 2 parts of butanol were subsequently added under vigorous stirring. The mixture was yet 1 hour vigorously stirred (ca. 260 rpm). Yielded composition was finally submitted to vacuum at 80°C during 2 hours to remove water. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in Table 1.
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80°C and 2.29 parts by weight of a 25% solution of NaOH were under stirring (210 rpm) added. The mixture was for 1 hour vigorously stirred (ca. 260 rpm). 6.67 parts by weight of a silica sol (Bindzil ® PC300, Eka Nobel, Sweden) and 2 parts of hexanol were subsequently added under vigorous stirring. The mixture was yet 1 hour vigorously stirred (ca. 260 rpm). Yielded composition was finally submitted to vacuum at 80°C during 2 hours to remove water. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in Table 1.
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80°C and 2.29 parts by weight of a 25% solution of NaOH were under stirring (210 rpm) added. The mixture was for 1 hour vigorously stirred (ca. 260 rpm). 6.67 parts by weight of a silica sol (Bindzil ® PC300, Eka Nobel, Sweden) and 2 parts of pentanol were subsequently added under vigorous stirring. The mixture was yet 1 hour vigorously stirred (ca. 260 rpm). Yielded composition was finally submitted to vacuum at 80°C during 2 hours to remove water. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in Table 1.
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80 °C and 2.29 parts by weight of a 25% NaOH solution was under stirring (210 rpm) added. This mixture was for 1 hour vigorously stirred (ca. 260 rpm) at 80 °C. Yielded composition was finally submitted to vacuum during 2 hours to remove water. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in Table 1.
- alkyd resin 1 100 parts by weight of alkyd resin 1 was heated to 80°C and 2.29 parts by weight of a 25% solution of NaOH were under stirring (210 rpm) added. The mixture was for 1 hour vigorously stirred (ca. 260 rpm) and 1 part by weight of a solution of cobalt/zirconium drier (6%Co and 9%Zr) was subsequently added. Resulting mixture was for yet 1 hour vigorously stirred (ca. 260 rpm) at 80°C. Yielded composition was finally submitted to vacuum at 80°C during 2 hours to remove water. Drying properties, at 40% non-volatile content, was recorded on a Beck-Koller Drying Recorder at a wet filmthickness of 75 ⁇ 5 ⁇ . The result is given in Table 1.
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AU2012363414A AU2012363414B2 (en) | 2011-12-29 | 2012-12-20 | Alkyd resin composition comprising silica |
BR112014015841A BR112014015841A8 (en) | 2011-12-29 | 2012-12-20 | alkyd resin composition comprising silica |
US14/369,155 US9932492B2 (en) | 2011-12-29 | 2012-12-20 | Alkyd resin composition comprising silica |
CA2859765A CA2859765C (en) | 2011-12-29 | 2012-12-20 | Alkyd resin composition comprising silica |
EP12861194.4A EP2798015A4 (en) | 2011-12-29 | 2012-12-20 | Alkyd resin composition comprising silica |
US15/699,338 US20170369734A1 (en) | 2011-12-29 | 2017-09-08 | Alkyd resin composition comprising silica |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US201161581407P | 2011-12-29 | 2011-12-29 | |
US61/581,407 | 2011-12-29 |
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US14/369,155 A-371-Of-International US9932492B2 (en) | 2011-12-29 | 2012-12-20 | Alkyd resin composition comprising silica |
US15/699,338 Division US20170369734A1 (en) | 2011-12-29 | 2017-09-08 | Alkyd resin composition comprising silica |
Publications (1)
Publication Number | Publication Date |
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WO2013100836A1 true WO2013100836A1 (en) | 2013-07-04 |
Family
ID=48698113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SE2012/000209 WO2013100836A1 (en) | 2011-12-29 | 2012-12-20 | Alkyd resin composition comprising silica |
Country Status (6)
Country | Link |
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US (2) | US9932492B2 (en) |
EP (1) | EP2798015A4 (en) |
AU (1) | AU2012363414B2 (en) |
BR (1) | BR112014015841A8 (en) |
CA (1) | CA2859765C (en) |
WO (1) | WO2013100836A1 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104086761B (en) * | 2014-06-05 | 2016-03-02 | 华南理工大学 | A kind of waterborne organic silicon modified alkyd resin and preparation method thereof |
EP3075458A1 (en) | 2015-04-03 | 2016-10-05 | Holland Novochem Technical Coatings B.V. | Process for applying a multilayer coating |
WO2018004334A2 (en) | 2016-06-29 | 2018-01-04 | Holland Novochem Technical Coatings B.V. | Adhesion promoter for coatings on metal surfaces |
US20190256736A1 (en) * | 2018-02-20 | 2019-08-22 | The Yenkin-Majestic Paint Corporation | UV-Curable Coating or Ink Composition |
GB2619262A (en) | 2022-04-04 | 2023-12-06 | H K Wentworth Ltd | Single component UV curable conformal coating with moisture secondary cure function |
Citations (5)
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EP0457939A1 (en) * | 1990-05-21 | 1991-11-27 | BASF Corporation | Paint rheology control additive containing hydrophobic colloidal silica |
JP2001294630A (en) * | 2000-04-11 | 2001-10-23 | Nippon Paint Co Ltd | Aqueous resin and method for producing the same |
WO2008049679A1 (en) * | 2006-10-27 | 2008-05-02 | Evonik Degussa Gmbh | Film-forming binders containing nanoscale particles and featuring enhanced scratch resistance and flexibility, processes for their preparation, and high-transparency coating materials containing them |
US20100178519A1 (en) * | 2009-01-14 | 2010-07-15 | Keimfarben Gmbh & Co. Kg | Compound coating for wood |
WO2012130763A1 (en) * | 2011-03-25 | 2012-10-04 | Akzo Nobel Chemicals International B.V. | Alkyd-based coating composition |
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GB1562651A (en) * | 1976-07-20 | 1980-03-12 | Kansai Paint Co Ltd | Surface treatment of metals |
US4196107A (en) * | 1978-06-05 | 1980-04-01 | Ppg Industries, Inc. | Semi-solid water-based coating compositions |
US4285846A (en) * | 1980-04-28 | 1981-08-25 | Cabot Corporation | Flatted water-reducible coating compositions and method for producing same |
US6015855A (en) * | 1997-01-31 | 2000-01-18 | Elisha Technologies Co Llc | Paint formulations |
EP1236765A1 (en) * | 2001-02-28 | 2002-09-04 | hanse chemie GmbH | Silica dispersion |
ATE542863T1 (en) * | 2001-03-15 | 2012-02-15 | Cabot Corp | MATTE THIXOTROPIC PAINT COMPOSITION |
US20050256262A1 (en) * | 2004-03-08 | 2005-11-17 | Alain Hill | Coating or composite moulding or mastic composition comprising additives based on cellulose microfibrils |
KR101694806B1 (en) * | 2009-03-13 | 2017-01-10 | 아크조 노벨 케미칼즈 인터내셔널 비.브이. | Aqueous silanized silica dispersion |
EP2493955A1 (en) * | 2009-10-30 | 2012-09-05 | Dow Global Technologies LLC | Alkyd dispersion, and a process for producing the same |
-
2012
- 2012-12-20 EP EP12861194.4A patent/EP2798015A4/en not_active Withdrawn
- 2012-12-20 BR BR112014015841A patent/BR112014015841A8/en not_active Application Discontinuation
- 2012-12-20 AU AU2012363414A patent/AU2012363414B2/en not_active Ceased
- 2012-12-20 CA CA2859765A patent/CA2859765C/en not_active Expired - Fee Related
- 2012-12-20 US US14/369,155 patent/US9932492B2/en not_active Expired - Fee Related
- 2012-12-20 WO PCT/SE2012/000209 patent/WO2013100836A1/en active Application Filing
-
2017
- 2017-09-08 US US15/699,338 patent/US20170369734A1/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0457939A1 (en) * | 1990-05-21 | 1991-11-27 | BASF Corporation | Paint rheology control additive containing hydrophobic colloidal silica |
JP2001294630A (en) * | 2000-04-11 | 2001-10-23 | Nippon Paint Co Ltd | Aqueous resin and method for producing the same |
WO2008049679A1 (en) * | 2006-10-27 | 2008-05-02 | Evonik Degussa Gmbh | Film-forming binders containing nanoscale particles and featuring enhanced scratch resistance and flexibility, processes for their preparation, and high-transparency coating materials containing them |
US20100178519A1 (en) * | 2009-01-14 | 2010-07-15 | Keimfarben Gmbh & Co. Kg | Compound coating for wood |
WO2012130763A1 (en) * | 2011-03-25 | 2012-10-04 | Akzo Nobel Chemicals International B.V. | Alkyd-based coating composition |
Non-Patent Citations (1)
Title |
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See also references of EP2798015A4 * |
Also Published As
Publication number | Publication date |
---|---|
CA2859765C (en) | 2016-12-13 |
EP2798015A4 (en) | 2015-08-26 |
EP2798015A1 (en) | 2014-11-05 |
AU2012363414B2 (en) | 2016-03-24 |
US20170369734A1 (en) | 2017-12-28 |
US9932492B2 (en) | 2018-04-03 |
BR112014015841A8 (en) | 2017-07-04 |
US20140360408A1 (en) | 2014-12-11 |
BR112014015841A2 (en) | 2017-06-13 |
AU2012363414A1 (en) | 2014-07-03 |
CA2859765A1 (en) | 2013-07-04 |
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