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
  • 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

Definitions

• the present invention relates to air-drying or semi-drying alkyd paints. More particularly, it relates to high-solids alkyd paints.
• high-solids refers to coatings with at most about 250g/l of volatile organic compounds (VOC) .
• High solids paints have long been known. However, they did not have the performances of the presently known paints that have a higher solvent content. There is thus a demand for high-solids paints that have performances at least as good as those which everyone is presently expecting in the art.
• EP-357128-A discloses an alkyd-type reactive diluent.
• EP-301345-A discloses a polyesterurethane containing ether groups and prepared from an isocyanate containing at least one copolymerisable double or triple carbon-carbon bond, used as reactive diluent for oxidatively drying binders.
• US-4609706 discloses the use of hydroxy-functional oligomer reacted with a compound containing both one ethylenic unsaturation and one isocyanate functionality as reactive diluent for drying oil modified alkyd resin.
• Another object of the invention is to provide air-drying or semi-drying alkyd paints of higher hiding power.
• Still another object of the invention is to provide air-drying or semi-drying alkyd paints having improved drying properties.
• Yet another object is to provide air-drying or semi-drying alkyd paints which can be applied in thicker layers without sagging.
• a further ob ect is to provide air-drying or semi-drying alkyd paints having an improved balance of the above objects.
• Still a further object of the invention is to provide a reactive diluent that can be used in combination with conventional air-drying or semi-drying long-oil or medium-oil alkyd resins to formulate high-solids air-drying or semi-drying alkyd paints meeting one or more of the above objects.
• the high-solids air-drying or semi-drying alkyd paints of the invention essentially comprise as binder a conventional air-drying or semi-drying long-oil or medium-oil alkyd resins.
• Alkyd resins are well-known in the art and need not be further described herein. They are the reaction product of the esterification of polyols with polybasic acids (or anhydrides) and fatty acids. Since the fatty acids act as chain terminators in the polyesterification reactions, the molecular weight is (among others) inversely dependent from the relative amount of fatty acids.
• the alkyd resins used as binder in the paints of the invention are classified as "long oil” or “medium oil” and contain from 45 to 70 wt% of fatty acids calculated as triglycerides, preferably from 60 to 65wt% (Percentage oil length refers to the oil portion of an alkyd expressed as a weight percentage of the alkyd; it is equal to the total weight of fatty acids taken together with the weight of glycerol needed to completely esterify these fatty acids minus the weight of evolved water of esterification, expressed as percentage of the total solids in the alkyd).
• the fatty acids used in the preparation of the alkyd resins must have an iodine number greater than 125 (semi-drying) or preferably 140 (drying) , expressed in terms of the number of centigrams of iodine per gram of fatty acids (e.g. ASTM test method D-1959).
• the resins preferably have an acid number (defined as mgKOH required to neutralize 1 g) smaller than 10.
• the high-solids air-drying or semi-drying alkyd paints of the invention further comprise a reactive diluent which essentially consists of an oligomer which can be prepared by the reaction of a polyisocyanate, a polyol and fatty acids.
• the polyisocyanate is an aliphatic and/or aromatic polyisocyanate (i.e. not containing any copolymerisable double or triple carbon-carbon bond) , preferably a diisocyanate
• the polyol has between 3 and 10 free alcohol groups, preferably about 6, and may contain at most one ether group per molecule. Aliphatic polyols are preferred.
• the oligomer (or mixture of oligo ers) is prepared with from 0.70 to 0.80 mole of fatty acids having an iodine number greater than 125, preferably greater than 140 particularly for use in air-drying paints, and from 0.20 to 0.10 mole of isocyanate group in the polyisocyanate per mole of hydroxyl in the polyol, such as to obtain isocyanate number equal to zero, acid number below 10 (preferably below 5), hydroxyl number between 10 and 30, and a viscosity comprised between 1 and 30 dPa.s preferably between 10 and 20 dPa.s (viscosity as used herein is measured at 23°C with a Haake viscosimeter, using a spindle E100 at rotation speed nr.l).
• the cure-process in air-drying or semi-drying involves oxidation, i.e. reaction with oxygen from the air. It is always performed in the presence of a catalyst, usually called “drier” or “siccative", which is usually a combination of metal salts.
• drier or "siccative"
• Suitable driers are metal salts of (cyclo)aliphatic. natural or synthetic acids, such as, for example, linoleic acid, naphtenic acid and 2-ethyl-hexanoic acid, and cobalt, manganese, lead, zirconium, calcium and zinc may be mentioned as suitable metals. Mixtures of driers can, of course, also be used. In terms of
• the driers are used in a proportion of 10 to about
• the paints of the invention also contain, if appropriate, solvents/diluents (i.e. non-reactive compounds that do not remain in the dry coating), pigments, fillers and auxiliaries (particularly anti-settling and/or anti-skinning additives) . .Amounts of those components are such that the paints have a VOC content of at most about 250 g/1, preferably 100 g/1 at most.
• the invention also relates to coating compositions having a VOC content of at most 250 g/1 and containing the air-drying or semi-drying long-oil or medium-oil alkyd resins described above as essential binder, the oligomers described above, according to the invention, as essential reactive diluent, driers and also, if appropriate, solvents/diluents, pigments, dyes, fillers and auxiliaries.
• the reactive diluents according to the invention it is possible to prepare coating compositions based on air-drying or semi-drying long-oil or medium-oil alkyd resins having a high solids content and meeting one or more objects of this invention.
• the coating agents according to the invention have a solids content within the range from 80 to 100% by volume (corresponding e.g. to the German "Blue Angel" requirements). It is thus also possible, by means of the reactive diluents according to the invention, to prepare readily brushable coating compositions based on air-drying or semi-drying long-oil or medium-oil alkyd resins in the absence of solvent/diluent.
• solvent/diluent as used herein comprises all usual solvents/diluents, such as white spirit, or even water (up to about 5 vol%) .
• the invention also relates to a process for the preparation of the coating compositions according to the invention, in which the alkyd resin binders, the oligomer prepared in accordance with the invention, at least one drier and also, if appropriate, solvents/diluents, pigments, dyes, fillers, auxiliaries and driers are processed by mixing and, if appropriate, dispersion and grinding, to give a coating composition.
• the weight ratio of binder to reactive diluent is of form 90:10 to 50:50, preferably of about 2:1. It can easily be adjusted by adding one or the other in the paint composition until the desired viscosity (generally between 5 and 15 dPa.s, preferably between 7.5 and 12 dPa.s, for brush or roller application) is obtained.
• the coating compositions according to the invention are particularly suitable for use as decorative paints. They can be applied in adequately high layer thicknesses and they have good hiding power and drying properties. In addition to this, the complete drying properties in particular can also be assessed as very good (whilst drying of one layer of certain compositions according to the invention may not be improved over the prior art, it is one advantage of the invention that since hiding power is improved, there is generally no need for a second layer so that overall drying is then improved) .
• the film formation of the coating compositions depends essentially on an oxidative drying; of course, if solvents are used, physical drying also takes place.
• the pigment volume concentration (PVC) should be adapted to the end use of the compositions, as known in the art; for example, varnishes have a PVC of zero, high gloss paints generally of up to about 20, maintenance paints generally of from 10 to 30 and primers generally of from 30 to 45.
• a conventional alkyd resin (hereinafter "A") is prepared in the known manner from soya oil, pentaerythritol and phthalic anhydride to obtain a resin with a phthalic anhydride content of 25wt%, an oil length of 64%, and a viscosity of 39 dPa.s when diluted as a 75wt% solution in white spirit.
• RD oligomer
• alkyd A 23.368 pbw reactive diluent RD 12.582 pbw solvents/diluents 16.872 pbw driers (solid) 2.888 pbw titanium dioxide, rutile 35.852 pbw additives 1.237 pbw fillers and extenders 6.573 pbw
• the resulting paint had a density of 1.389 g/ml, a viscosity of 9.5 dPa.s at 23°C (measured with a Haake VT181 viscosimeter, using a spindle E100 at rotation speed nr.l), a PVC of 23.3%, a fineness comprised between 0.025 and 0.030 mm and contained 246g of volatile organic compounds (VOC) per litre.
• VOC volatile organic compounds
• the paint could be applied in layers of maximum thickness of at least 0.04mm without sagging (maximum dry film thickness according to ASTM test method D4400-89a using procedure A) .
• a leveling rating of "9" was determined using ASTM test method D2801-69.
• the drying properties were measured at 23°C and 50% relative humidity with a BK-drying recorder (Sheen Instruments Ltd.) :
• the average contrast ratio measured according to ISO 2814-1973 on a 0.03 mm film was of 96.44%.

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• Chemical & Material Sciences (AREA)
• Wood Science & Technology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Paints Or Removers (AREA)
• Polyesters Or Polycarbonates (AREA)
• Polyurethanes Or Polyureas (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Solid-Sorbent Or Filter-Aiding Compositions (AREA)
• Application Of Or Painting With Fluid Materials (AREA)
• Paper (AREA)

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• 1994
  • 1994-10-28 DE DE69422777T patent/DE69422777T2/de not_active Expired - Lifetime
  • 1994-10-28 WO PCT/BE1994/000077 patent/WO1995012641A1/en not_active Ceased
  • 1994-10-28 PT PT94870170T patent/PT651039E/pt unknown
  • 1994-10-28 AT AT94870170T patent/ATE189253T1/de not_active IP Right Cessation
  • 1994-10-28 AU AU79869/94A patent/AU7986994A/en not_active Abandoned
  • 1994-10-28 DK DK94870170T patent/DK0651039T3/da active
  • 1994-10-28 ES ES94870170T patent/ES2142922T3/es not_active Expired - Lifetime
  • 1994-10-28 EP EP94870170A patent/EP0651039B1/en not_active Expired - Lifetime
  • 1994-10-28 SI SI9430299T patent/SI0651039T1/xx unknown
  • 1994-11-01 US US08/332,690 patent/US6075088A/en not_active Expired - Lifetime
  • 1994-11-22 TW TW083110835A patent/TW313581B/zh active
• 2000
  • 2000-04-25 GR GR20000400991T patent/GR3033308T3/el not_active IP Right Cessation

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