WO1999038926A1 - Compositions filmogenes autoxidisables et ecologiques de polymeres d'alkyde pour revetements - Google Patents

Compositions filmogenes autoxidisables et ecologiques de polymeres d'alkyde pour revetements Download PDF

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Publication number
WO1999038926A1
WO1999038926A1 PCT/EP1999/000331 EP9900331W WO9938926A1 WO 1999038926 A1 WO1999038926 A1 WO 1999038926A1 EP 9900331 W EP9900331 W EP 9900331W WO 9938926 A1 WO9938926 A1 WO 9938926A1
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WO
WIPO (PCT)
Prior art keywords
autoxidisable
alkyd
anhydroalditol
mixture
coating composition
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Application number
PCT/EP1999/000331
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English (en)
Inventor
Philip Louis Taylor
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Imperial Chemical Industries Plc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Plc filed Critical Imperial Chemical Industries Plc
Priority to AU26199/99A priority Critical patent/AU2619999A/en
Publication of WO1999038926A1 publication Critical patent/WO1999038926A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/46—Polyesters chemically modified by esterification
    • C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • 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

  • This invention relates to environmentally friendly autoxidisable film-forming alkyd polymer coating compositions such as paint, varnish or woodstain in which the alkyd polymer contains a large proportion of material obtainable from renewable resources without any substantial degradation of properties as compared to conventional alkyd polymer coating compositions.
  • the invention especially relates to coating compositions suitable for application at ambient temperatures (e.g. 5 to 40°C) to architectural surfaces such as those found on buildings or their fittings or furnishings.
  • the invention also relates to autoxidisable film-forming alkyd polymers suitable for use in the coating composition.
  • autoxidisable is synonymous with “drying” or “air drying” . All three terms mean that when a coating of the autoxidisable film-forming material is applied to a surface and exposed to air in the presence of an autoxidation catalyst (such as calcium, zirconium or cobalt octoate or naphthenate) , the alkyd polymer will crosslink or "dry” to form a macromolecular film by oxidation involving the olefinic unsaturation which is found in alkyd polymers.
  • the macromolecular film serves to protect the surface and to bind together any non-film-forming components of the coating composition such as pigments and extenders.
  • Alkyd polymers are amongst the oldest protective binder materials used in paints.
  • the alkyd polymers generally used in coating compositions for - 2 -
  • architectural surfaces usually comprise high molecular weight dicarboxylate polymer chains having molecular weights in the range 200 to 200,000 with chains having molecular weights above 100,000 being important in assisting alkyd paints to dry quickly at ambient temperatures. This is particularly important if coatings applied in a thickness of from 100 to 200 ⁇ m are to be able to dry without wrinkling. 1 ⁇ m is 10 ' *m.
  • dicarboxylates made by esterifying an aromatic dicarboxylic acid or its anhydride with a substituted polyol which is an alcohol or ether alcohol originally containing at least three alcoholic hydroxyl groups but nowadays containing more than three in order to obtain the amounts of higher molecular weight chains needed for quicker drying.
  • a substituted polyol which is an alcohol or ether alcohol originally containing at least three alcoholic hydroxyl groups but nowadays containing more than three in order to obtain the amounts of higher molecular weight chains needed for quicker drying.
  • At least two of these hydroxyl groups esterify pairs of dicarboxylic acid or anhydride molecules whilst most of the remainder are substituted by an autoxidisable hydrocarbylcarbonyl moiety, i.e.
  • R is a partially olefinically unsaturated hydrocarbon chain (such as is found in linolenic acid) generally containing 9 to 29 (usually 16 or 18) carbon atoms.
  • Typical autoxidisable hydrocarbylcarbonyl moieties include those derivable from autoxidisable natural oils such as linseed, cottonseed, corn, rapeseed, soya bean and tung oils and tall oil fatty - 3 -
  • Typical of the dicarboxylic acids are isophthalic, succinic, adipic and sebacic acids whilst phthalic anhydride is typical of the anhydrides.
  • Typical alcoholic polyols in commercial use are the alcohols and ether alcohols such as trimethylol propane, glycerol, pentaerythritol and di- and tripentaerythritol. Glycerol is of course obtainable from renewable resources, but it results in slow- drying alkyd polymers.
  • alkyd dicarboxylate polymer made using isophthalic acid and substituted pentaerythritol would contain a predominant proportion of units as represented below
  • RC0 2 - represents a hydrocarbylcarbonyloxy moiety made autoxidisable by the presence of olefinic unsaturation in the hydrocarbyl part of the moiety.
  • Esterification is usually performed until the acid value of the alkyd ester has fallen to below lOmgKOH/g of the ester.
  • a typical modern alkyd polymer suitable for use in architectural paints can therefore in principle be described as a high molecular weight polymeric aromatic dicarboxylic ester of low acid value (e.g. below lOmgKOH/g of the ester) containing mainly divalent esterifying groups which are polyols having more than three hydroxyl groups of which at least one is esterified by an autoxidisable hydrocarbylcarbonyl or "oil" moiety.
  • the oil components of commercial alkyd polymers have the advantage of being largely derivable from agricultural products which are of course renewable sources. They are also easily biogradable when buried in landfill sites which is advantageous when large quantities of waste or surplus paint need to be discarded.
  • EP 0 668 305B mentions the possible use of polyols such as sorbitol, mannitol or glucose (page 2 line 52) which contain more than three hydroxyl groups and which are obtainable from renewable resources but attempts to use these in commercial alkyd manufacture result in highly discoloured polymers which can only be used in dark coloured paints.
  • the present invention seeks to provide an autoxidisable film-forming alkyd polymer coating composition wherein the alkyd polymer is a polyester of a polyol containing more than three hydroxyl groups which is obtainable from renewable resources but which does not have the same extent of disadvantage shown by alkyd polymers obtained from polyols such as sorbitol, mannitol or glucose.
  • this invention provides an environmentally friendly autoxidisable film-forming alkyd polymer coating composition which comprises liquid carrier, autoxidation catalyst (for example a calcium, cobalt or zirconium carboxylate) and autoxidisable film-forming alkyd/polymer at least some of which is a polyester of a polycarboxylate (preferably a dicarboxylate) and a polyol containing more than three hydroxyl groups at least some of which hydroxyl groups are esterified by autoxidisable hydrocarbylcarbonyl moieties characterised in that the polyol comprises an anhydroalditol, preferably a 2,5 anhydroalditol .
  • autoxidation catalyst for example a calcium, cobalt or zirconium carboxylate
  • autoxidisable film-forming alkyd/polymer at least some of which is a polyester of a polycarboxylate (preferably a dicarboxylate) and a polyol containing more than three hydroxyl
  • This invention also provides a process for preparing - 6 -
  • an autoxidisable film-forming alkyd polymer which comprises reacting an anhydroalditol mixture with a dicarboxylic acid or anhydride thereof in the presence of an autoxidisable natural oil, wherein the anhydroalditol mixture has been obtained by: i) subjecting a starch hydrolysate obtained by hydrolysing a starch, or a sugar, to heterogeneous catalytic hydrogenolysis to produce an alditol mixture, and ii) subjecting the alditol mixture to heterogeneous catalytic cyclodehydration to produce the anhydroalditol mixture.
  • This invention additionally provides a substrate comprising a coating of a cured coating composition as defined above.
  • the invention further provides the use of an anhydroalditol as a polyol component in an autoxidisable alkyd film-forming polymer.
  • the coating composition of the present invention does not discolour as much as coating compositions containing alkyd polymers obtained from polyols such 20 as sorbitol, mannitol, or glucose.
  • the compositions may, for example, also dry as quickly as conventional alkyd coating compositions. - 7 -
  • the 2,5 isomers are preferred because they resist further dehydration to form dianhydroalditols which have only two hydroxyl groups.
  • the invention also provides an environmentally friendly autoxidisable film-forming alkyd polymer which is a polyester of a polycarboxylate (preferably a dicarboxylate) and a polyol containing more than three hydroxyl groups at least some of which are esterified by autoxidisable hydrocarbylcarbonyl moieties characterised in that the polyol comprises an anhydroalditol, preferably a 2,5 anhydroalditol.
  • the alkyd polymers of this invention can be used to make coating compositions having drying times and light colours comparable with those of conventional alkyd formulations.
  • they can be used to make coating compositions containing about 15 wt% rutile titanium dioxide which when applied to a standard white surface in a thickness of 100 ⁇ m and allowed to dry completely, produce dried coats having an NCS greyness factor of less than 60 as defined by the Swedish Standard SS 01 91 03.
  • the first step if a starch is used as a raw material, is to perform a conventional aqueous hydrolysis of the starch, preferably by means of an enzyme such as «-amylase, whereupon there is produced a so-called aqueous starch hydrolysate of uncertain composition.
  • the starch hydrolysate, or the sugar is next subjected to heterogeneous catalytic hydrogenolysis preferably using ruthenium supported on a large pore zeolite at 130 to 150°C and 5 to 20 Mpa (50 to 200 bar) hydrogen pressure. Hydrogenolysis produces an aqueous mixture of alditols including sorbitol.
  • aqueous alditol mixture is then subjected to heterogeneous catalytic cyclodehydration preferably using palladium supported on activated carbon at 250 to 300°C and 5 to 15 Mpa (50 to 150 bar) hydrogen pressure in the presence of an acidic catalyst such as a dispersed acidic zeolite of the H-Y or H-ZSM5 types or alternatively a dissolved acid such as propionic acid.
  • an acidic catalyst such as a dispersed acidic zeolite of the H-Y or H-ZSM5 types or alternatively a dissolved acid such as propionic acid.
  • the above mixture of anhydroalditols may be used directly as the polyol in a conventional condensation polymerisation for the production of alkyd polymers.
  • the mixture may be blended with conventional polyols (such as pentaerythritol or dipentaerythritol) to give minor variations in the properties of the alkyd polymer. For example, up to - 9 -
  • 60wt%, for example 15 to 60wt%, of the polyol may be conventional polyol.
  • a further variation comprises blending alkyd made according to this invention with totally conventional alkyd, for example an alkyd made using pentaerythritol as the polyol.
  • Preferably such a blend comprises up to 60wt%, for example from 15 to 60wt%, of the conventional alkyd.
  • the alkyd polymers and blends according to this invention may be formulated into coating compositions by mixing with a liquid carrier and preferably one or more conventional non-film-forming materials of the type found in paints, varnishes and woodstains. Such materials include inorganic or organic pigments, dyes, extenders, thickeners, structuring agents, fungicides, anti-skinning agents, flow improvers and drying agents.
  • the liquid carrier is preferably an organic solvent such as white spirit. However, it may also be an aqueous carrier containing the alkyd polymer in the form of an emulsion and a suitable surfactant as is well known in the art. Suitably in the latter case the alkyd polymer has an oil length of 30 to 80%, preferably 35 to 60%.
  • the coating compositions should preferably have a cone and plate viscosity at 25°C of at least 1 and preferably at least 1.5 poise (i.e. 0.1 and 0.15 Pa.s) to ensure that wet coatings have acceptable sag- resistance when applied to a vertical surface and preferably not more than 10 poise (lPa.s) so as to enable them to be applied by brush, pad or roller at ambient temperatures.
  • compositions according to the invention can, if desired, accommodate more solid materials (over 75wt% and usually over 80wt%) which in turn means that they can contain less organic solvent.
  • Less solvent is an environmental advantage because the solvent is lost to the atmosphere when the composition dries and it has been recently acknowledged that solvent from drying paints causes a significant proportion of modern atmospheric pollution.
  • the "solid", i.e. "nonvolatile” material is the content of the liquid composition which remains to form a dried coat of the composition after all the volatile components of the liquid coating compositions have been lost by evaporation.
  • the molecular weights of the various polymeric materials are determined by gel permeation chromatography. A 0.5wt% solution of material in tetrahydrofuran was passed at lml/min through cylindrical columns 300mm long by 20mm diameter packed with a gel available from Polymer Laboratories Limited - 11 -
  • a coating 100 ⁇ m thick is applied at 20°C to a horizontal glass sheet.
  • a hopper having a small outlet in its base is filled with sand which then trickles through the outlet.
  • the hopper is caused to traverse the coating at a speed of 25.4mm/hour with sand trickling onto the coating.
  • the sand sticks to the coating which is still wet but as time passes, the coating dries and there comes a point when the sand ceases to stick to it.
  • the time taken to reach this point is regarded as the touch dry time for the purposes of the specification.
  • the point is easily detected by blowing the loose sand from the fully dried coating so as to leave a trail of stuck sand of a length from which the touch dry time is calculated by dividing the speed of traverse.
  • An aqueous mixture of anhydroalditols was obtained from potato starch by first subjecting the starch to a conventional enzymatic hydrolysis using «-amylase, which produced a solution consisting of 20wt% starch hydrolysate in water.
  • This aqueous starch hydrolysate was subjected to 5 hours of hydrogenolysis at 150 ⁇ C and 5 to 20 Mpa (50 to 200 bar) pressure of hydrogen in the presence a ruthenium catalyst supported on a large pore zeolite of the Y type. 5wt% of catalyst (based on the weight of the starch hydrolysate) was used and the ruthenium made up lwt% of the weight of the supported catalyst.
  • the supported catalyst was filtered off, whereupon an aqueous mixture of alditols was obtained.
  • the water content of the mixture was adjusted by distillation to give an aqueous mixture containing 50wt% of alditols.
  • the alditols were then converted to anhydroalditols by adding, to the 50wt% aqueous mixture, 5wt% propionic acid as an acid catalyst and 1 wt% of a catalyst comprising palladium supported on activated carbon where the weight percentages of both catalysts are based on the weight of alditols present in the 50wt% aqueous mixture.
  • the palladium made up lwt% of the supported catalyst.
  • aqueous alditol and catalysts mixture was cyclodehydrated at 270°C and 7 Mpa (70 bar) - 13 -
  • a 5 litre glass flask was fitted with a stirrer and a Dean and Stark reflux condenser operable so as to allow the escape of water from an azeotropic solvent.
  • the flask was purged with nitrogen and then charged with:
  • the agitator blade of the mixer was operated at 1,500 rpm for 30 minutes.
  • the paint had a solids content of 69.2wt%.
  • a primed surface was prepared by priming a hardboard surface with "Dulux” Trade white alkyd wood primer (available from ICI Paints of Slough, England) and then allowing the primed surface to age at ambient temperatures for seven days.
  • a coating lOO ⁇ m thick of the paint was applied to the primed surface using a block spreader and the surface was mounted vertically. No sagging of the coating was observed during the period of 30 minutes following application which is the time when sagging is most likely to occur.
  • a coating 100 ⁇ m thick was also subjected to the drying Time Measurement as described above. It was found to dry in two and a half hours.
  • a conventional alkyd polymer and paint were made according to Example l except that the whole of the anhydroalditol was replaced by pentaerythritol.
  • the conventional paint obtained had a viscosity of 0.33 Pa.s (3.3 poise).
  • a 100 ⁇ m coating of the conventional paint was subjected to the Drying Time measurement and found to dry in 2.5 hours.
  • a dried 100 ⁇ m coat of the paint was assessed for colour using a spectrophotometer and found to be very similar to that of Example 1.
  • Dissolved alkyd polymer was made according to Example l except that 33wt% of the anhydroalditol mixture was replaced by pentaerythritol during the preparation of the alkyd polymer to provide a polymer in which the diol consists of 50wt% pentaerythritol and 50wt% of the anhydroalditol mixture.
  • the amount of white spirit in the alkyd polymer solution was varied to produce alternative solutions as in Example 1 and the graph of cone and plate viscosity at 25°C against alkyd polymer content was plotted and is shown as the curve for Alkyd 2 in Figure 1.
  • Figure 1 shows that the viscosity of the alkyd solution reaches 1 Pa.s (10 poise) at a solids content of about 77wt%.
  • Dissolved alkyd polymer was made according to Example 1 except that the weights used were as shown below and the preparation was carried out at 250 ⁇ C.
  • the anhydroalditol mixture was the same as that obtained in the first part of Example 1.
  • the final acid value of the polymer was 9.6 mg KOH/g and the corresponding paint had a viscosity of 0.32 Pa.s (3.2 poise) and a drying time of 3 hours.
  • Dissolved alkyd polymer was made according to Example 1 except that the weights used were as shown below: Charge Parts by Weight
  • the final acid value of the polymer was 12.0 mg KOH/g and the corresponding paint had a drying time of 5.25 hours.
  • the colour of the paint was poor (yellow) and when measured using a Lovibond colorimeter was found to be twice as yellow as the paint from Comparative Example A.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention porte sur une composition filmogène autoxidisable et écologique de polymères d'alkyde pour revêtements comportant: un support liquide; un catalyseur d'autoxidation; et un polycarboxylate et un polyol à plus de trois groupes hydroxyles dont certains sont estérifiés par des fragments autoxidisables d'hydrocarbylcarbonyle, ledit polyol étant un anhydroalditol.
PCT/EP1999/000331 1998-01-31 1999-01-21 Compositions filmogenes autoxidisables et ecologiques de polymeres d'alkyde pour revetements WO1999038926A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU26199/99A AU2619999A (en) 1998-01-31 1999-01-21 Environmentally friendly autoxidisable film-forming alkyd polymer coating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9802057.1 1998-01-31
GBGB9802057.1A GB9802057D0 (en) 1998-01-31 1998-01-31 Environmentally friendly autoxidisable film-forming alkyd polymer coating compositions

Publications (1)

Publication Number Publication Date
WO1999038926A1 true WO1999038926A1 (fr) 1999-08-05

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AU (1) AU2619999A (fr)
CA (1) CA2260487A1 (fr)
GB (1) GB9802057D0 (fr)
WO (1) WO1999038926A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003064498A1 (fr) * 2002-01-30 2003-08-07 Sigma Coatings B.V. Compositions de peinture sechant a l'air, comportant des polyesters a base glucidique
WO2007074334A2 (fr) * 2005-12-24 2007-07-05 Croda International Plc Compositions de revetement et diluants reactifs pour leur preparation
EP2835390A1 (fr) * 2013-08-05 2015-02-11 A Et A Mader Résine alkyde biosourcée et procédé de fabrication d'une telle résine alkyde
WO2018048638A1 (fr) 2016-09-07 2018-03-15 Arkema Inc. Compositions polymères alkydes et formulations de produit formées à partir de ces dernières
CN112771050A (zh) * 2018-09-27 2021-05-07 阿科玛股份有限公司 用于生产快干醇酸聚合物的含环醚和羟基的组合物及制备此类含环醚和羟基的组合物的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1456107A (en) * 1973-09-27 1976-11-17 Bayer Ag Air-drying alkyd resins containing co-condensed monoalcohol
EP0234899A2 (fr) * 1986-02-21 1987-09-02 Kao Corporation Composition de toner
EP0280780A1 (fr) * 1987-02-04 1988-09-07 Hüls Aktiengesellschaft Mélanges de compositions prédéterminées de polyols à base de sorbitol, leur procédé de préparation et leur utilisation dans la préparation d'esters de sorbitane

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1456107A (en) * 1973-09-27 1976-11-17 Bayer Ag Air-drying alkyd resins containing co-condensed monoalcohol
EP0234899A2 (fr) * 1986-02-21 1987-09-02 Kao Corporation Composition de toner
EP0280780A1 (fr) * 1987-02-04 1988-09-07 Hüls Aktiengesellschaft Mélanges de compositions prédéterminées de polyols à base de sorbitol, leur procédé de préparation et leur utilisation dans la préparation d'esters de sorbitane

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003064498A1 (fr) * 2002-01-30 2003-08-07 Sigma Coatings B.V. Compositions de peinture sechant a l'air, comportant des polyesters a base glucidique
WO2007074334A2 (fr) * 2005-12-24 2007-07-05 Croda International Plc Compositions de revetement et diluants reactifs pour leur preparation
WO2007074334A3 (fr) * 2005-12-24 2007-08-23 Croda Int Plc Compositions de revetement et diluants reactifs pour leur preparation
US10131741B2 (en) 2013-08-05 2018-11-20 A Et A Mader Biosourced alkyd resin and method for manufacturing such an alkyd resin
WO2015019020A1 (fr) * 2013-08-05 2015-02-12 A Et A Mader Résine alkyde biosourcée et procédé de fabrication d'une telle résine alkyde
EP2835390A1 (fr) * 2013-08-05 2015-02-11 A Et A Mader Résine alkyde biosourcée et procédé de fabrication d'une telle résine alkyde
WO2018048638A1 (fr) 2016-09-07 2018-03-15 Arkema Inc. Compositions polymères alkydes et formulations de produit formées à partir de ces dernières
CN109642108A (zh) * 2016-09-07 2019-04-16 阿科玛股份有限公司 醇酸聚合物组合物及由其形成的产品制剂
EP3510113A4 (fr) * 2016-09-07 2020-04-01 Arkema Inc. Compositions polymères alkydes et formulations de produit formées à partir de ces dernières
US11814477B2 (en) 2016-09-07 2023-11-14 Arkema Inc. Alkyd polymer compositions and product formulations formed therefrom
CN112771050A (zh) * 2018-09-27 2021-05-07 阿科玛股份有限公司 用于生产快干醇酸聚合物的含环醚和羟基的组合物及制备此类含环醚和羟基的组合物的方法
EP3856746A4 (fr) * 2018-09-27 2022-06-22 Arkema Inc. Compositions contenant un éther cyclique et un hydroxyle, utiles pour produire des polymères d'alkyde secs rapides et procédés de fabrication de telles compositions contenant un éther cyclique et un hydroxyle
CN112771050B (zh) * 2018-09-27 2024-01-19 阿科玛股份有限公司 用于生产快干醇酸聚合物的含环醚和羟基的组合物及制备此类含环醚和羟基的组合物的方法
US11912820B2 (en) 2018-09-27 2024-02-27 Arkema Inc. Cyclic ether- and hydroxyl-containing compositions useful for producing fast dry alkyd polymers and methods for making such cyclic ether- and hydroxyl-containing compositions

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GB9802057D0 (en) 1998-03-25
CA2260487A1 (fr) 1999-07-31
AU2619999A (en) 1999-08-16

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