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WO2017048169A1 - Procédé de production de liant de revêtement dispersible dans l'eau et séchant à l'air - Google Patents

Procédé de production de liant de revêtement dispersible dans l'eau et séchant à l'air Download PDF

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Publication number
WO2017048169A1
WO2017048169A1 PCT/SE2016/000046 SE2016000046W WO2017048169A1 WO 2017048169 A1 WO2017048169 A1 WO 2017048169A1 SE 2016000046 W SE2016000046 W SE 2016000046W WO 2017048169 A1 WO2017048169 A1 WO 2017048169A1
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WO
WIPO (PCT)
Prior art keywords
acid
diisocyanate
process according
polyol
fatty acid
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/SE2016/000046
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English (en)
Inventor
Ramakrishnan Subramanian
Bhushan SAINDANE
Saurabh KUSURKAR
Kent Sorensen
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Perstorp AB
Original Assignee
Perstorp AB
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Filing date
Publication date
Application filed by Perstorp AB filed Critical Perstorp AB
Publication of WO2017048169A1 publication Critical patent/WO2017048169A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters

Definitions

  • the present invention refers to a process for producing a water dispersible, air drying coating binder comprising the following steps: a) producing an alkyd by reacting at least one unsaturated fatty acid and/or at least one corresponding triglyceride, at least one polyol and at least one polycarboxylic acid b) reacting the product obtained in a) by adding at least one hydroxyfunctional
  • the present invention also refers to a coating composition produced by neutralising the acid groups of a coating binder produced by said process and dispersing said neutralised coating binder in water.
  • Polyurethanes are a very broad group of polymers differing widely in composition and properties. These compounds are characterised by having urethane groups -NH-CO-O- formed by polyaddition of hydroxyfunctional compounds, typically diols, triols or polyols, to the -NCO groups of di-, tri-, or polyfunctional isocyanates.
  • Aqueous dispersions of polyurethanes are well known in production of coating compositions. They may be used for protective or decorative coating, optionally in combination with additives like dyes, pigments, matting agents and the like. Polyurethanes exhibit many desirable properties, such as good chemical resistance, water resistance, solvent resistance, toughness, abrasion resistance and durability.
  • Air drying polyurethane dispersions are typically prepared using autoxidatively drying alkyd resins having terminal hydroxyl groups being reactive toward polyisocyanates.
  • Alkyd resins are polyesters which have been modified by the addition of for instance fatty acids and/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.
  • polyesters comprising, in addition to polyalcohols and polycarboxylic acids, monobasic acids, usually long-chain fatty acids, or corresponding triglycerides.
  • monobasic acids usually long-chain fatty acids, or corresponding triglycerides.
  • fatty acid/triglyceride confers a tendency to form flexible coatings.
  • Air drying polyurethane dispersions modified with fatty acids and/or corresponding triglycerides represent a synergistic combination of air drying alkyd resins and polyurethanes, thus combining the excellent property profiles of both polymer types.
  • Chain extension is a chemical procedure commonly used for raising the molecular weight of polymers. An increased molecular weight of the polymer will improve the mechanical properties of a coating based on that polymer.
  • Chain extension can for example be performed by adding an amine to the polymer.
  • low molecular weight amines such as ethylene diamine, are toxic, and some are easily absorbed through the skin. It is therefore desirable to use as little as possible of these chemicals and instead use other molecules than amines for the chain extension process.
  • a polyol is used for the chain extension step.
  • the present invention discloses a new process for producing a water dispersible, air drying coating binder.
  • the coating binder disclosed is based on an alkyd which is reacted with a hydroxyfunctional carboxylic acid and a polyisocyanate to form a polyurethane and chain extended with a polyol.
  • Disclosed is also a coating composition produced by neutralising the acid groups of a coating binder produced by the process according to the invention and dispersing said neutralised coating binder in water.
  • Coating compositions of the present invention have shown good hardness and very good drying properties. This, together with the dispersibility in water and the amine-free chain extension step makes coating compositions of the present invention an excellent choice for, for example, outdoor paints.
  • poly is defined as two or more.
  • Air drying means autoxidatively drying in the context of the present invention.
  • the present invention refers to a process for producing a water dispersible, air drying coating binder comprising the following steps: a) producing an alkyd by reacting at least one unsaturated fatty acid and/or at least one corresponding triglyceride, at least one polyol and at least one polycarboxylic acid b) reacting the product obtained in a) by adding at least one hydroxyfunctional
  • the first step of the process according to the invention is to produce an alkyd, according to methods well known in the art.
  • At least one unsaturated fatty acid, at least one polyol and at least one polycarboxylic acid are charged together in a suitable reaction vessel, optionally together with an azeotropic solvent, like for example xylene.
  • the temperature is raised to about 200-260 °C and an esterification reaction takes place between the unsaturated fatty acid, the polyol and the polycarboxylic acid.
  • at least one triglyceride may be transesterified with at least one polyol and thereafter esterified with at least one
  • polycarboxylic acid optionally at least one polyol and optionally at least one unsaturated fatty acid.
  • Said unsaturated fatty acid is preferably chosen from the group consisting of soybean fatty acid, linseed fatty acid, tall oil fatty acid, safflor fatty acid and/or sunflower fatty acid, but also fatty acids like for example linoleic acid, linolenic acid, palmitic acid, ricinoleic acid and/or dehydrated castor oil fatty acid can be used or, as mentioned above, a corresponding triglyceride.
  • Polyols used in the alkyd syntheses step 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-l ,3-dioxanes, di(hydroxyalkyl)furans, di(hydroxyalkyl)tetrahydrofurans, 2-alkyl- 1,3 -propanediols, 2,2-dialkyl-l,3-propanediols, 2- hydroxyalkyl- 1 ,3 -propanediols, 2,2-dihydroxyalkyl- 1 ,3 -propanediols, 2-alkyl-2- hydroxyalkyl- 1,3 -propanediols, as well as polyalkoxylated, such
  • polyols include dendritic polyester and/or polyether polyalcohols.
  • Said polyols can suitably be 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- 1 ,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
  • Preferred polyols are pentaerythritol, di-pentaerythritol, trimethylolethane,
  • trimethylolpropane trimethylolbutane, di-trimethylolethane, di-trimethylolpropane, di- trimethylolbutane, neopentylglycol, glycerol and /or di-glycerol.
  • Polycarboxylic acids that can be used in the 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, isophthalic acid, terephthalic acid, 1,2- cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4- cyclohexanedicarboxylic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic anhydride, fumaric acid, adipic acid, azelaic acid, succinic acid, sebacic acid, furandicarboxylic acid, tetrahydrofurandicarboxylic acid, trimelletic acid, itaconic acid, citraconic acid, pyromelletic acid and/or, when applicable, their corresponding anhydrides .
  • o-phthalic acid is
  • polycarboxylic acids are phthalic acid, isophthalic acid, maleic anhydride, azelaic acid, adipic acid, tetrahydrophthalic acid, hexahydrophthalic acid, furanedicarboxylic acid, itaconic acid, succinic acid and/or, when applicable, their corresponding anhydrides.
  • the alkyd resin prepared in a) has a hydroxyl number between 30-220 mg KOH/g, preferably between 60-120 mg KOH/g.
  • the acid number is below 10 mg KOH/g and preferably below 5 mg KOH/g.
  • the alkyd produced in step a) is reacted with at least one hydroxyfunctional carboxylic acid and at least one polyisocyanate, to produce a polyurethane in step b).
  • the alkyd and the hydroxyfunctional carboxylic acid are charged together with a suitable solvent, like for example ketones like methylethylketone, acetone or N-Methyl-2-pyrrolidone.
  • the polyisocyanate is added and the mixture is heated to about 60-100 °C.
  • a catalyst for example dibutyl tin dilaurate, can be added together with the polyisocyanate at a concentration of 0.01- 0.1%, calculated on prepolymer.
  • Suitable hydroxyfunctional carboxylic acids include, but are not limited to, dimethylolpropionic acid, dimethylolbutyric acid, trihydroxymethylacetic acid, 2,2- dihydroxymethylvaleric acid, tartaric acid, dihydroxymalonic acid, dihydroxybenzoic acid and/or hydroxypivalic acid.
  • the hydroxyfunctional carboxylic acid is dimethylolpropionic acid.
  • the polyisocyanate used in step b) can be for example 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 tnisocyanate.
  • Further suitable isocyanate based components include isocyanurates, biurets and allophanates.
  • the polyisocyanate used in step b) is isophorone diisocyanate.
  • the polyurethane produced in step b) is chain extended in step c) by addition of a suitable polyol at a temperature of about 60-100°C.
  • suitable polyols for the chain extension step are ethyleneglycol, 1,2-propanediol, 1,3 -propanediol, 1,4-butylene glycol, 1,3-butylene glycol, neopentyl glycol, 2-butyl-2-ethyl-l,3-propanediol, 1 ,6-hexanediol and/or cyclohexanedimethanol.
  • the polyol used in step c) is neopentylglycol, ethyleneglycol and/or 2-butyl-2-ethyl-l,3-propanediol. According to a more preferred embodiment of the present invention, the polyol used in step c) is ethyleneglycol.
  • the carboxylic groups of the product produced in step c) need to be neutralised.
  • the present invention also refers to a coating composition produced by neutralising the acid groups of a coating binder produced by the process according to the invention and dispersing said neutralised coating binder in water.
  • the acid groups of the coating binder are neutralised by addition of a volatile (at ambient conditions) tertiary amine, such as triethylamine.
  • a volatile (at ambient conditions) tertiary amine such as triethylamine.
  • the neutralisation can also be made by adding for example ammonia, sodium hydroxide, potassium hydroxide and/or lithium hydroxide.
  • the coating composition additionally comprises additives like dyes, pigments, matting agents, fillers, flow and/or levelling additives and the like.
  • a drier is added to the coating binder, before it is being neutralised and dispersed in water.
  • Said drier can for example be derived from ions of cobalt, manganese, zirconium, calcium and/or iron.
  • Coating compositions according to the present invention may be used for protective or decorative coating on various substrates like for example metal, wood, plastic and/or paper.
  • Example 1 illustrates the invention and refers to synthesis of an alkyd from soy bean fatty acid (SOFA), pentaerythritol and phthalic anhydride.
  • SOFA soy bean fatty acid
  • pentaerythritol pentaerythritol
  • phthalic anhydride soy bean fatty acid
  • Example 2 illustrates the invention and refers to preparation of an alkyd polyurethane dispersion chain extended with ethyleneglycol.
  • Example 3 illustrates the invention and refers to preparation of an alkyd polyurethane dispersion chain extended with neopentylglycol.
  • Example 4 illustrates the invention and refers to preparation of an alkyd polyurethane dispersion chain extended with 2-butyl-2-ethyl-l,3-propanediol.
  • Example 5 shows some evaluation data for the alkyd polyurethane dispersions produced in Examples 2-4.
  • EXAMPLE 1 Synthesis of Alkyd Polyol-Long oil SOFA
  • the resulting alkyd polyol-long oil SOFA had an acid number of 1.97 mg KOH/g, an OH-value of 98.1 mg KOH/g and a viscosity of 400 mPas (Brookfield) @23°C Sp 03/6 rpm.
  • EXAMPLE 2 Coating binder chain extended with Ethyleneglycol (MEG), neutralised and dispersed in water
  • the prepolymer was chain extended by addition of 1.26 parts per weight of ethyleneglycol and the reaction was continued until the NCO-content was 0.52%. 1.72 parts per weight of triethylamine was added to neutralise the acid groups. The prepolymer was dispersed into 55.81 parts per weight of water. The resulting dispersion was yellowish translucent, had a viscosity of 94 mPas (Brookfield) @23°C Sp 01 , a solid content (105°C /3h) of 35.21 % and a pH-value of 7.41.
  • EXAMPLE 3 Coating binder chain extended with Neopentylglycol (Neo), neutralised and dispersed in water
  • the prepolymer was chain-extended by addition of 2.08 parts per weight of neopentylglycol and the reaction was continued until the NCO-content was 1.12%. 1.71 parts per weight of triethylamine was added to neutralise the acid groups.
  • the prepolymer was dispersed into 55.34 parts per weight of water. The resulting dispersion was white translucent and had a viscosity of 27 mPas (Brookfield) @23°C Sp 01, a solid content (105°C /3h) of 35.12% and a pH -value of 7.3.
  • EXAMPLE 4 Coating binder chain extended with 2-butyl-2-ethyl-l,3-propanediol (BEPD), neutralised and dispersed in water
  • the prepolymer was chain-extended by addition of 4.1 1 parts per weight of 2-butyl-2-ethyl-l,3- propanediol (BEPD) and the reaction was continued until the NCO-content was 0.58 %. 1.67 parts per weight of triethylamine was added to neutralise the acid groups.
  • the prepolymer was dispersed into 54.20 parts per weight of water. The resulting dispersion was yellowish translucent, had a viscosity of 98 mPas (Brookfield) @23°C Sp 01 , a solid content (105°C /3h) of 35.12% and a pH- value of 7.4.
  • EXAMPLE 5 Evaluation data
  • the alkyd polyurethane dispersions produced in Examples 2, 3 and 4 were evaluated in coating compositions. Drying agent Oxycoat was used (1% on polyurethane dispersion).
  • Drying properties (dry film thickness 25 microns) were measured for the alkyd polyurethane dispersion chain extended with ethyl eneglycol (Ex 2). The results are shown in Table 2 below.

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

Abstract

La présente invention concerne un procédé de production d'un liant de revêtement dispersible dans l'eau et séchant à l'air comprenant les étapes suivantes consistant à : a) produire un alkyde en faisant réagir au moins un acide gras insaturé et/ou au moins un triglycéride correspondant, au moins un polyol et au moins un acide polycarboxylique ; b) faire réagir le produit obtenu au cours de l'étape a) en ajoutant au moins un acide carboxylique à fonction hydroxy et au moins un polyisocyanate afin de produire un polyuréthane ; c) rallonger la chaîne du polyuréthane obtenu au cours de l'étape b) en ajoutant au moins un polyol. La présente invention concerne également une composition de revêtement produite en neutralisant les groupes acide d'un liant de revêtement produit par ledit procédé et en dispersant dans l'eau ledit liant de revêtement neutralisé.
PCT/SE2016/000046 2015-09-17 2016-09-07 Procédé de production de liant de revêtement dispersible dans l'eau et séchant à l'air Ceased WO2017048169A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2935DE2015 2015-09-17
IN2935/DEL/2015 2015-09-17

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Publication Number Publication Date
WO2017048169A1 true WO2017048169A1 (fr) 2017-03-23

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111133064A (zh) * 2017-09-19 2020-05-08 宣伟投资管理有限公司 包含含呋喃的聚酯的涂料组合物、制品以及涂布方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57209960A (en) * 1981-06-19 1982-12-23 Harima Kasei Kogyo Kk Polyol for use as main component for two-pack urethane paint
JPH07166130A (ja) * 1993-12-14 1995-06-27 Dainippon Ink & Chem Inc 水性ウレタン化アルキッド樹脂分散体
JP2008007717A (ja) * 2006-06-30 2008-01-17 Toyobo Co Ltd ウレタン変性アルキッド樹脂、水系ウレタン変性アルキッド塗料用樹脂組成物およびそれらの製造方法
US20080146748A1 (en) * 2006-11-17 2008-06-19 Harald Blum Polyurethane-modified alkyd resin dispersions
CN102432797A (zh) * 2011-08-18 2012-05-02 山东圣光化工集团有限公司 端羟基醇酸树脂改性水性聚氨酯及其制备方法
CN103073706A (zh) * 2012-12-25 2013-05-01 东莞大宝化工制品有限公司 一种类似水性的净味油性聚氨酯面漆及其制备方法
EP2889318A1 (fr) * 2013-12-31 2015-07-01 ALLNEX AUSTRIA GmbH Résine Alkyde Aqueuse Modifiée

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57209960A (en) * 1981-06-19 1982-12-23 Harima Kasei Kogyo Kk Polyol for use as main component for two-pack urethane paint
JPH07166130A (ja) * 1993-12-14 1995-06-27 Dainippon Ink & Chem Inc 水性ウレタン化アルキッド樹脂分散体
JP2008007717A (ja) * 2006-06-30 2008-01-17 Toyobo Co Ltd ウレタン変性アルキッド樹脂、水系ウレタン変性アルキッド塗料用樹脂組成物およびそれらの製造方法
US20080146748A1 (en) * 2006-11-17 2008-06-19 Harald Blum Polyurethane-modified alkyd resin dispersions
CN102432797A (zh) * 2011-08-18 2012-05-02 山东圣光化工集团有限公司 端羟基醇酸树脂改性水性聚氨酯及其制备方法
CN103073706A (zh) * 2012-12-25 2013-05-01 东莞大宝化工制品有限公司 一种类似水性的净味油性聚氨酯面漆及其制备方法
EP2889318A1 (fr) * 2013-12-31 2015-07-01 ALLNEX AUSTRIA GmbH Résine Alkyde Aqueuse Modifiée

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GÄHDE, J. ET AL.: "Increase in coating wet adhesion stability by highly-ordered polymers", J. ADHESION SCI. TECHNOL., vol. 11, no. 6, 1997, pages 861 - 875, XP055371906, ISSN: 0169-4243 *
NAIK, R. B.: "Synthesis and characterization of novel hyperbranched alkyd andisocyanate trimer based high solid polyurethane coatings", PROGRESS IN ORGANIC COATINGS, vol. 77, no. 2, February 2013 (2013-02-01), pages 369 - 379, XP055318618 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111133064A (zh) * 2017-09-19 2020-05-08 宣伟投资管理有限公司 包含含呋喃的聚酯的涂料组合物、制品以及涂布方法

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