WO2007074334A2 - Compositions de revetement et diluants reactifs pour leur preparation - Google Patents

Compositions de revetement et diluants reactifs pour leur preparation Download PDF

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Publication number
WO2007074334A2
WO2007074334A2 PCT/GB2006/004841 GB2006004841W WO2007074334A2 WO 2007074334 A2 WO2007074334 A2 WO 2007074334A2 GB 2006004841 W GB2006004841 W GB 2006004841W WO 2007074334 A2 WO2007074334 A2 WO 2007074334A2
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WO
WIPO (PCT)
Prior art keywords
fatty acid
oil
acid ester
polyunsaturated fatty
coating composition
Prior art date
Application number
PCT/GB2006/004841
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English (en)
Other versions
WO2007074334A3 (fr
Inventor
Hanamanthsa Shankarsa Bevinakatti
Wilhelmus Jacobus Adrianus Honcoop
Original Assignee
Croda International Plc
Uniqema, Bv
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 Croda International Plc, Uniqema, Bv filed Critical Croda International Plc
Publication of WO2007074334A2 publication Critical patent/WO2007074334A2/fr
Publication of WO2007074334A3 publication Critical patent/WO2007074334A3/fr

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Classifications

    • 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
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • 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
    • C09D7/20—Diluents or solvents

Definitions

  • the present invention relates to coating compositions and reactive diluents therefor.
  • the present invention relates to coating compositions such as paints, varnishes and wood stains containing reactive diluents prepared from alditols and unsaturated fatty acids and to such reactive diluents per se.
  • Coating compositions based on alkyd resins are in very wide spread use owing to the ease of applicability of such compositions to various substrates and to subsequent adhesion, protective properties and aesthetic appearance of the polymeric film formed from such compositions on drying. In many applications, the compositions air dry as the alkyd resins are auto-oxidisable in air.
  • Such reactive diluents act as solvents for the alkyd resins but are subsequently incorporated into the polymeric network formed as the composition dries, ie the reactive diluent is essentially non-volatile or at most of low volatility thus enabling the presence of volatile organic solvents in the composition to be at least significantly reduced if not eliminated entirely.
  • Examples of the use of such reactive diluents in alkyd resin coating compositions may be found in EP-A-0685543, US 4689266, US 4798859, US 5064892 and WO 03/064548.
  • Suitable reactive diluents an important factor in selecting suitable reactive diluents is the ability of the diluent to function as a solvent for the alkyd resin components, ie to have a suitable viscosity to impart the correct viscosity range to the coating composition for its subsequent use, whilst having a low volatility.
  • a factor that affects the viscosity of reactive diluents based on fatty acid esters of polyols as described in the aforementioned prior disclosures is the number of free OH groups remaining in the molecules following esterification. As described in WO 03/064548, such free OH groups remaining in the carbohydrate precursor may be reduced or eliminated by further acetylating the fatty acid modified carbohydrate.
  • a coating composition comprises at least one binder and a reactive diluent therefor, said reactive diluent being obtainable by the reaction of at least one alditol with at least one polyunsaturated fatty acid or alkyl ester thereof under conditions to effect cyclisation of said alditol through anhydrisation thereof.
  • a reactive diluent in a coating composition of a polyunsaturated fatty acid ester compound obtainable by the reaction of at least one alditol with at least one polyunsaturated fatty acid or alkyl ester thereof under conditions to effect cyclisation of said alditol through anhydrisation thereof .
  • a third aspect of the invention comprises an unsaturated fatty acid ester of an alditol which is obtainable by the reaction of at least one alditol with at least one polyunsaturated fatty acid or alkyl ester thereof under conditions to effect cyclisation of said alditol through anhydrisation thereof wherein said ester has on average at least 3, more preferably at least 3.3 and more especially about 3.5 fatty acid ester groups per alditol residue and wherein on average at least 50 wt% of said fatty acid ester groups are polyunsaturated fatty acid ester groups, the remaining fatty acid ester groups being on average not more than 20 wt% saturated fatty acid ester groups and not more than 30 wt% monounsaturated fatty acid ester groups.
  • the reactive diluent is obtainable by the reaction of only said at least one alditol and said at least one polyunsaturated fatty acid or alkyl ester thereof under conditions to effect cyclisation of said alditol through anhydrisation thereof.
  • the fatty acid ester of an alditol is obtainable by the reaction of only said at least one alditol and said at least one polyunsaturated fatty acid or alkyl ester thereof under conditions to effect cyclisation of said alditol through anhydrisation thereof.
  • the reactive diluent has on average less than one free OH group per alditol residue, more especially on average less than 0.5 free OH group per alditol residue.
  • the reactive diluent has a free OH group hydroxyl value of not more than 20 mgKOH/g, more preferably not more than 15 mgKOH/g and more especially not more than 10 mgKOH/g.
  • the reactive diluent has a free OH group hydroxyl value of around 5 mgKOH/g or less. It is to be noted that, in measuring hydroxyl values, the resultant figure is a combination of residual acid OH groups and residual alcohol OH groups. Accordingly, in this specification, the expression "free OH group hydroxyl value” is the difference between the total hydroxyl value and the acid value (which is also expressed in mgKOH/g).
  • the alditols used to obtain reactive diluents and fatty acid esters of alditols in accordance with the present invention are unsubstituted alditols, ie the alditols do not have any substituents substituted for or in any of their hydroxyl groups.
  • the alditols are selected from C 4 to C 6 alditols (including mixtures thereof). More preferably, the alditols are selected from C 5 and C 6 alditols.
  • the alditols are selected from hexitols, more particularly from sorbitol or mannitol. In an especially preferred embodiment, the alditol is sorbitol.
  • Suitable polyunsaturated fatty acids for use in the present invention are the semi- drying or drying polyunsaturated fatty acids or mixtures thereof that are ethylenically unsaturated, whether conjugated or non-conjugated. More particularly, the acids are selected from Ci 8 to C 22 polyunsaturated fatty acids and may be linoleic, linolenic, arachindonic, eicosatetraenoic, eicosapentaenoic and docasahexaenoic acids or mixtures thereof. More especially, the acids are selected from C 18 to C 20 polyunsaturated fatty acids or mixtures thereof. In a particularly preferred embodiment, the polyunsaturated fatty acid is linoleic acid.
  • the polyunsaturated fatty acids are derived from natural or synthetic oils in which the preferred acids are a major component, other acids being present in minor amounts.
  • the raw oils themselves may be used; preferably, however, the polyunsaturated acids are the distilled fractions obtained from the raw oils.
  • suitable natural oils include but are not limited to safflower oil, tall oil, calendula oil, corn oil, rapeseed oil, peanut oil, soya bean oil, tung oil, linseed oil, sardine oil, herring oil, sesame oil, olive oil, dehydrated castor oil, tallow oil, sunflower oil, cottonseed oil and mixtures thereof.
  • the polyunsaturated fatty acid is linoleic acid
  • the linoleic acid is preferably derived from sunflower oil or soya bean oil.
  • distilled fatty acid fractions derived from such oils are used to make the reactive diluent of the present invention, such distilled fractions having at least 50 wt% polyunsaturated fatty acids.
  • the majority of the remaining balance being long chain saturated fatty acids, preferably no more than about 20 wt%, and mono-unsaturated fatty acids, preferably no more than about 30 wt%.
  • the long chain saturated fatty acids are C 14 to C 20 or greater fatty acids and the mono-unsaturated fatty acid is C 18 mono-unsaturated fatty acid.
  • Such polyunsaturated fatty acids are auto-oxidisable similarly to alkyd resins and the distilled fatty acid fractions used in the reactive diluent of the present invention preferably have an iodine number of at least 100, more preferably of at least 120 and preferably up to around 140 expressed in terms of the number of centigrams of iodine per gram of fatty acids (eg ASTM test method D-1959).
  • alkyl esters of the polyunsaturated fatty acids are used, preferably it is a C 1 to C 6 alkyl ester, more preferably it is a C 1 to C 4 alkyl ester and even more preferably is a C 1 to C 2 aikyl ester. Mixtures esters may also be used.
  • reactive diluents of the present invention have viscosity of not more than 0.5 Pa s at 25°C, preferably not more than 0.25 Pa s at 25 0 C and more especially not more than 0.2 Pa s at 25°C.
  • reaction conditions for making the reactive diluent according to the invention are selected to minimise the formation of other products, for example mono-, di- and tri-esters of the alditol.
  • reaction conditions are also selected to minimise the formation of isosorbide.
  • the resultant ester has on average at least 3, more preferably at least 3.3 and more especially about 3.5 fatty acid ester groups per sorbitan residue and wherein on average at least 50 wt% of said fatty acid ester groups are linoleate ester groups, the remaining fatty acid ester groups being on average not more than 20 wt% saturated fatty acid ester groups and not more than 30 wt% monounsaturated fatty acid ester groups.
  • the reactive diluent according to the invention is made by reacting alditol(s) with polyunsaturated fatty acid(s) in the presence of acid and base catalysts, for example phosphorous acid and sodium hydroxide.
  • acid and base catalysts for example phosphorous acid and sodium hydroxide.
  • the alditol(s) and the catalysts may be charged to a suitable reaction vessel as aqueous solutions.
  • the water is distilled off by heating the reaction mixture to temperatures of not more than about 140 0 C, preferably not more than about 130 0 C.
  • the temperature of the reaction mixture is then increased to about 220 0 C to 260 0 C, typically about 240°C, to cyclise the alditol(s) through anhydrisation thereof and to effect the esterification reaction.
  • the esterification reaction may be direct, inter- or trans- esterification or a combination thereof.
  • the reaction is terminated after the acid value of the reaction mixture has dropped to a suitable level, typically less than 25 mgKOH/g, more particularly less than 20 mgKOH/g and more especially less than 10 mgKOH/g.
  • anhydrous alditol(s) may be used; although such starting materials are not preferred owing to their cost.
  • the binders of the coating compositions of the present invention are preferably auto- oxidisable alkyd resins.
  • alkyd resins are in general the reaction product of the esterification of polyhydric alcohols with polybasic acids (or their anhydrides) and fatty acids (or glycerol esters thereof) and need not to be further described herein.
  • the properties of the alkyd resins are primarily determined by the nature and the ratios of the alcohols and acids used and by the degree of condensation.
  • Suitable alkyd resins include long oil and medium oil resins eg derived from 45 to 70 wt. % of fatty acids.
  • the binder may also be selected from (meth)acrylic-modified alkyd resins, vinylated alkyd resins, styrene alkyd resins, polyurethane alkyd resins, silicone alkyd resins, polyamide modified alkyds and epoxy esters.
  • the coating composition according to the present invention preferably has a binder to reactive diluent ratio in the range from 98 to 50 : 2 to 50 parts by weight, more preferably from 95 to 50 : 5 to 40 and more especially from 90 to 70 : 10 to 30 parts by weight.
  • the coating compositions according to the present invention may be formulated by any conventional mixing techniques including, as appropriate, dispersing and grinding with a liquid carrier and at least one drier and optionally pigments, filler/extenders and other conventional additives.
  • Suitable solvents include aliphatic, cycloaliphatic and aromatic hydrocarbons, alcohol ethers, alcohol ether esters, alcohol esters and mixtures thereof.
  • suitable solvents include aliphatic, cycloaliphatic and aromatic hydrocarbons, alcohol ethers, alcohol ether esters, alcohol esters and mixtures thereof.
  • Typical examples of such solvents are: butyl glycol butyl diglycol - isoparafins propylene glycol mono methyl ether dipropylene glycol mono methyl ether white spirits including de-aromatised and higher flash point white spirits.
  • the solvent is typically present at about 10 to about 20 wt% and preferably about 10 to about 15 wt%.
  • driers for example the commercial material available under the trade name Nuodex, preferably incorporated in the range 0.1% to 10% by weight based on the binder.
  • suitable driers are salts of (cyclo)aliphatic, natural or synthetic acids, such as, for example, linoleic acid, naphthenic acid, 2-ethyl-hexanoic acid and neodecanoic acid of various metal like cobalt, manganese, iron, lead, zirconium, strontium, aluminium, calcium, barium, bismuth, zinc, lithium and potassium.
  • an anti-skinning agent such as a ketoxime, typically methyl ethyl ketoxime, n-butyl ketoxime or cyclohexane ketoxime, may be present in the coating composition.
  • Other additives to the coating composition according to the present invention may include rheology modifiers, wetting and compability agents, flow and levelling agents, extenders, anti-sagging agents, anti-oxidants, bactericides, fungicides, insecticides, UV absorbers, flame retardants and other additives that are well known in the art.
  • Coating compositions according to the present invention will optionally comprise one or more inorganic or organic, transparent or non-transparent pigments.
  • pigments may be selected from titanium dioxide, iron oxides, carbon black, mixed metal oxides, mono- and di- azo pigments, copper phthalocyanines and anthraquinones.
  • coating compositions according to the present invention are typically used, for coating substrates such as wood, plastics, leather, textiles, glass, ceramic or meta ⁇ s.
  • the coating compositions according to the present invention may be applied to such substrates by any known methods, such as spraying, brushing, flooding, casting, dipping and rolling.
  • Acid Value The acid value was determined using ASTM D1980-87.
  • the hydroxyl value was determined using ASTM D1957-86.
  • the viscosity was determined using ISO 2555.
  • Molecular weight was determined by gel permeation chromatography (GPC) using a Viscotek Evolution system consisting of a solvent pump, vacuum degasser, autosampler, column oven and refractive index detector.
  • Tetrahydrofuran was used as the mobile phase at a flow rate of 1 ml/min, along with a set of two ViscoGel (TSK GMHHR) columns. Column and detector temperature was maintained at 40 0 C. Polystyrene standards were used for determination of molecular weight information.
  • the drying time was determined using a drying time recorder from Byk-Gard ⁇ er. K ⁇ nig Hardness
  • the K ⁇ nig hardness was determined using DIN/ISO 1522. Yellowing Index
  • the yellowing Index was determined using ASTM E313 96. Gloss Gloss was determined using DIN/ISO 2813.
  • Samples 1 and 2 - of alditol esters suitable as reactive diluents according to the invention were prepared by charging 156.Og 70% aqueous sorbitol solution (109.2g , 0.6 mol; sorbitol and 46.8g water), 588.0g (2.1 mol) of fatty acid, 3.Og (6.1 mol % based on sorbitol) phosphorous acid and 5.Og 50% aqueous sodium hydroxide solution (10.4 mol% based on sorbitol) were charged to a 1000ml round bottomed flask fitted with a propeller stirrer, side-arm water condenser and collection flask, nitrogen sparge and thermometer (thermocouple), the flask being mounted on an isomantle.
  • aqueous sorbitol solution 109.2g , 0.6 mol; sorbitol and 46.8g water
  • 588.0g (2.1 mol) of fatty acid 3.Og
  • the fatty acid was a distilled sunflower fatty acid fraction available from Uniqema under the trade mark PRIFAC 8960; and, in the preparation of Sample 2, the fatty acid was a distilled soya bean fatty acid fraction available from Uniqema under the trade mark PRIFAC 8953.
  • the reaction mixture was heated using the isomantle under stirring (300 rpm), with a nitrogen sparge to distil off free water (mostly below 130 0 C) and the temperature was then increased to 240 0 C and held until the acid value of the reaction mix was ⁇ 10mgKOH/g (normally 7 - 8 hrs).
  • the reaction was then stopped by switching off the isomantle and the product cooled to ⁇ 100 0 C after which it was filtered under reduced pressure, using a 110mm buchner funnel fitted with a Whatman No 1 filter paper and dicalite filter aid. to remove catalyst residues.
  • Samples 1 and 2 had the properties shown in Table 1 below. Samples 1 and 2 of reactive diluents in accordance with the invention were particularly useful in formulating paint compositions.
  • a long oil alkyd resin formulation was made using the components shown in Table 2.
  • the long oil alkyd resin has the composition shown in Table 3.
  • the alkyd formulation had a viscosity of 1.095 Pa s at 23°C.
  • the formulation was tested for drying time, Konig hardness, yellowing and gloss retention as described above. The results are shown in Table 4. Table 4

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  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention concerne des compositions de revêtement comprenant au moins un liant, par exemple une résine alkyde, et un diluant réactif. Le diluant réactif est susceptible d'être obtenu par la réaction d'au moins un alditol avec au moins un acide gras polyinsaturé ou un ester d'alkyle de celui-ci dans des conditions entraînant une cyclisation dudit alditol via une anhydrisation de celui-ci. Un diluant réactif particulièrement préféré est susceptible d'être obtenu par la réaction de sorbitol avec de l'acide linoléïque. Dans des modes de réalisation préférés, les acides polyinsaturés sont dérivés d'huiles naturelles.
PCT/GB2006/004841 2005-12-24 2006-12-21 Compositions de revetement et diluants reactifs pour leur preparation WO2007074334A2 (fr)

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GB0526460.1 2005-12-24
GBGB0526460.1A GB0526460D0 (en) 2005-12-24 2005-12-24 Coating compositions and reactive diluents therefor

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WO2007074334A2 true WO2007074334A2 (fr) 2007-07-05
WO2007074334A3 WO2007074334A3 (fr) 2007-08-23

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009042770A1 (fr) * 2007-09-25 2009-04-02 Monsanto Technology Llc Utilisation d'huiles contenant des concentrations élevées d'acides gras polyinsaturés dans des matières plastiques et des revêtements de surface
WO2010020355A1 (fr) * 2008-08-18 2010-02-25 Cook Composites And Polymers Company Résine et compositions de revêtement de peinture comprenant des polyol-polyesters hautement estérifiés dotés d'une paire de liaisons doubles conjuguées ou plus
WO2010020361A1 (fr) * 2008-08-18 2010-02-25 Cook Composites And Polymers Company Résine et compositions de revêtement de peinture comprenant des polyol-polyesters hautement estérifiés dotés d'une paire de liaisons doubles conjuguées
EP3281993A1 (fr) * 2016-08-11 2018-02-14 Oleon N.V. Combinaison de diluants réactifs
WO2020068582A1 (fr) * 2018-09-27 2020-04-02 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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4698105A (en) * 1986-01-14 1987-10-06 Nippon Kayaku Kabushiki Kaisha Water-in-oil type emulsion explosives
US4798859A (en) * 1986-09-24 1989-01-17 Bayer Aktiengesellschaft Polyhydroxyl compounds containing ester and ether groups as reactive diluents
WO1999038926A1 (fr) * 1998-01-31 1999-08-05 Imperial Chemical Industries Plc Compositions filmogenes autoxidisables et ecologiques de polymeres d'alkyde pour revetements
US20050042379A1 (en) * 2002-01-30 2005-02-24 Oostveen Evarardus Arnoldus Reactive diluents and coatings comprising them

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4698105A (en) * 1986-01-14 1987-10-06 Nippon Kayaku Kabushiki Kaisha Water-in-oil type emulsion explosives
US4798859A (en) * 1986-09-24 1989-01-17 Bayer Aktiengesellschaft Polyhydroxyl compounds containing ester and ether groups as reactive diluents
WO1999038926A1 (fr) * 1998-01-31 1999-08-05 Imperial Chemical Industries Plc Compositions filmogenes autoxidisables et ecologiques de polymeres d'alkyde pour revetements
US20050042379A1 (en) * 2002-01-30 2005-02-24 Oostveen Evarardus Arnoldus Reactive diluents and coatings comprising them

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103897476B (zh) * 2007-09-25 2016-08-17 孟山都技术公司 具有高浓度多不饱和脂肪酸的油在塑料和表面涂料中的用途
WO2009042770A1 (fr) * 2007-09-25 2009-04-02 Monsanto Technology Llc Utilisation d'huiles contenant des concentrations élevées d'acides gras polyinsaturés dans des matières plastiques et des revêtements de surface
US9376580B2 (en) 2007-09-25 2016-06-28 Monsanto Technology Llc Use of oils with high concentrations of polyunsaturated fatty acids in plastics and surface coatings
CN103897476A (zh) * 2007-09-25 2014-07-02 孟山都技术公司 具有高浓度多不饱和脂肪酸的油在塑料和表面涂料中的用途
US8846781B2 (en) 2007-09-25 2014-09-30 Monsanto Technology Llc Use of oils with high concentrations of polyunsaturated fatty acids in plastics and surface coatings
WO2010020361A1 (fr) * 2008-08-18 2010-02-25 Cook Composites And Polymers Company Résine et compositions de revêtement de peinture comprenant des polyol-polyesters hautement estérifiés dotés d'une paire de liaisons doubles conjuguées
WO2010020355A1 (fr) * 2008-08-18 2010-02-25 Cook Composites And Polymers Company Résine et compositions de revêtement de peinture comprenant des polyol-polyesters hautement estérifiés dotés d'une paire de liaisons doubles conjuguées ou plus
EP3281993A1 (fr) * 2016-08-11 2018-02-14 Oleon N.V. Combinaison de diluants réactifs
WO2018029312A1 (fr) * 2016-08-11 2018-02-15 Oleon Nv Combinaison de diluants réactifs
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
WO2020068582A1 (fr) * 2018-09-27 2020-04-02 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
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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WO2007074334A3 (fr) 2007-08-23

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