EP0321502A1 - Liant en resine alkyde, sechant a l'air, son procede de production, enduit a base de ce liant en resine alkyde et son utilisation comme peinture pour batiments - Google Patents

Liant en resine alkyde, sechant a l'air, son procede de production, enduit a base de ce liant en resine alkyde et son utilisation comme peinture pour batiments

Info

Publication number
EP0321502A1
EP0321502A1 EP19870906662 EP87906662A EP0321502A1 EP 0321502 A1 EP0321502 A1 EP 0321502A1 EP 19870906662 EP19870906662 EP 19870906662 EP 87906662 A EP87906662 A EP 87906662A EP 0321502 A1 EP0321502 A1 EP 0321502A1
Authority
EP
European Patent Office
Prior art keywords
weight
drying
alkyd resin
trimethylolpropane
pentaerythritol
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.)
Pending
Application number
EP19870906662
Other languages
German (de)
English (en)
Inventor
Jörg Pronobis
Vijay Kadambande
Bodo Weber
Rolf Peter-Pollmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Farben und Fasern AG
Original Assignee
BASF Lacke und Farben AG
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 BASF Lacke und Farben AG filed Critical BASF Lacke und Farben AG
Publication of EP0321502A1 publication Critical patent/EP0321502A1/fr
Pending legal-status Critical Current

Links

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
    • C08G18/28—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
    • 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

Definitions

  • the present invention relates to air-drying alkyd resin binders produced from drying and / or semi-drying fatty acids, di- and / or polyols, part of the alcohols being replaced by di-trimethylolpropane and / or di-pentaerythritol, and di- and / or polycarboxylic acids.
  • the dimer of trimethylolpropane, di-trimethylolpropane, an alcohol with 4 primary hydroxyl groups, is recommended for use in air-drying alkyd resins and saturated polyester resins, whereby di-trimethylolpropane is intended to replace part of the polyol content.
  • this polyhydric alcohol only represents up to about a third of the total polyol content.
  • the modification with di-trimethylolpropane leads to an increased flexibility of the resulting coatings without influencing the degree of hardness .
  • the solids contents of the known alkyd resins modified with di-trimethylolpropane are below 70% by weight with an application viscosity.
  • the dimer of pentaerythritol, di-pentaerythritol, an alcohol with 6 primary hydroxyl groups is recommended as a raw material for alkyd resins for coating agents and printing inks.
  • the object of the present invention was to provide binders which can be air-dried coating compositions with a solids content of Have at least 70% by weight processed at application viscosity.
  • the resulting coating agents should have good drying properties with sufficiently high layer thicknesses.
  • Di-trimethylolpropane or di-pentaerythritol are to be understood as the dimers of trimethylolpropane or pentaerythritol which are linked to one another via two hydroxyl groups by an ether group.
  • di-pentaerythritol and / or di-trimethylolpropane in the above quantitative ratio surprisingly leads to low-viscosity binders which have a very good solubility in white spirit, although the alkyd resins have relatively high molecular weights.
  • the binders according to the invention are of low viscosity, they can be processed into coating compositions with a solids content of at least 70% by weight with an application viscosity.
  • the incorporation of di-pentaerythritol and / or di-trimethylolpropane in a certain quantitative ratio ensures that a relatively high proportion of fatty acids is incorporated, which leads to the good properties described.
  • the viscosities of the 80% solutions of the binders according to the invention in xylene are in the range from 2.0 to 12.0 dPa.s.
  • 80% strength solutions of the alkyd resin binders in white spirit have viscosities in the range from 2.0 to 10.0 dPa.s at 20 ° C.
  • the alkyd resins generally have acid numbers from about 2 to 20 mg KOH / g and hydroxyl numbers from about 2 to 100 mg KOH / g.
  • the alcohol component b) consists of more than 95% by weight of di-pentaerythritol and / or di-trimethylolpropane. 50 to 80% by weight of drying and / or semi-drying fatty acids are advantageously used as component a).
  • Suitable drying and / or semi-drying fatty acids which generally have 6 to 24 carbon atoms per molecule, are soybean oil fatty acid, safflower oil fatty acid, sunflower oil fatty acid, cottonseed oil fatty acid, castor oil fatty acid, tall oil fatty acid and linseed oil fatty acid.
  • non-drying fatty acids such as coconut oil fatty acid, isononanoic acid and alpha-ethylhexanoic acid, can also be used in part.
  • trimethylolpropane In addition to di-pentaerythritol and di-trimethylolpropane, trimethylolpropane, glycerin, ethylene glycol, neopentyl glycol, propylene glycol, 1,6-hexanediol, trimethylolethane, 1,4-dimethylolcyclohexane, 1,3-dimethylolcyclohexane, 1,2-cyclohexanediol and 1 , 4-cyclohexanediol in question.
  • Suitable di- and polycarboxylic acids are, for example, orthophthalic acid, terephthalic acid, trimellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, dimer fatty acids, adipic acid and azelaic acid.
  • diisocyanates e.g. 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, dicyclohexylmethane diisocyanate and hexamethylene-1,6-diisocyanate can also be used.
  • diisocyanates leads to the formation of urethane alkyds.
  • Suitable monocarboxylic acids are, for example, benzoic acid, para-tertiary butylbenzoic acid, abietic acid, pivalic acid, lauric acid, stearic acid, cyclopentane carboxylic acid and cyclohexane carboxylic acid.
  • the monocarboxylic acids can be used in a proportion of up to 20% by weight, based on the total weight of the alkyd resin building blocks.
  • the invention also relates to a method for producing the binders according to the invention, which is characterized in that
  • the alkyd resin formation takes place on the way of a polyesterification reaction well known to the person skilled in the art.
  • a catalyst for the formation of urethane can optionally be used.
  • a particularly suitable catalyst for polyurethane formation is dibutyltin dilaurate.
  • the alcohol component b) consists of more than 95% by weight of di-pentaerythritol and / or di-trimethylolpropane. 60 to 80% by weight of drying and / or semi-drying fatty acids are particularly advantageously used as component a).
  • the invention further relates to coating compositions with a solids content of at least 75% by weight, which contain the air-drying alkyd resins according to the invention described above as essential binders and, if appropriate, organic solvents, pigments, fillers, auxiliaries and dry matter Contain substances.
  • the alkyd resin binders according to the invention it is possible to produce coating compositions with a high solids content, so-called "high-solid lacquers", with application viscosity.
  • the binders according to the invention lead to a lowering of the viscosity in comparison to known alkyd resin binders.
  • the coating compositions according to the invention advantageously have a solids content in the range from 85 to 100% by weight. It is therefore also possible with the aid of the air-drying alkyd resins according to the invention to produce easily spreadable coating agents without solvents.
  • the coating compositions according to the invention can optionally contain pigments, fillers, auxiliaries and drying agents.
  • Pigments include both natural and synthetic, transparent and non-transparent pigments.
  • drying agents are metal salts (cyclo) -alliphatic, natural or synthetic acids, e.g. Linoleic acid, naphthenic acid and 2-ethylhexanoic acid, suitable metals being cobalt, manganese, lead, zirconium, calcium and zinc. Of course, mixtures of desiccants can also be used.
  • the dry substances are used in a proportion of 10 -3 to about 3% by weight, based on the solid binder.
  • the invention also relates to a process for the preparation of the coating compositions according to the invention, in which the alkyd resin binders prepared according to the invention and, if appropriate, organic solvents and pigments, fillers, auxiliaries and drying agents are processed into a coating composition by mixing and, if appropriate, dispersing.
  • the coating compositions according to the invention are particularly suitable for use as architectural coatings. They can be applied in sufficiently thick layers and have good drying properties.
  • the film formation of the coating agents is essentially based on an oxidative drying.
  • the invention is explained in more detail below on the basis of exemplary embodiments. Parts mean parts by weight unless otherwise stated.
  • the following exemplary embodiments are carried out in a reactor which has an agitator, a nitrogen feed line and a separation receiver which separates the azeotropic mixture of aromatics and water via a cooler.
  • the reactor can be heated electrically, inductively or by thermal oil.
  • the temperature is controlled by a thermometer that regulates the temperature of the work piece.
  • the components for the production of alkyd resins are weighed into the reactor. The removal of water takes place with the aid of entraining agents.
  • alkyd resin is produced from 753 parts of fatty acid, which is available under the brand name Juvandol, 195 parts of di-pentaerythritol and 114 parts of phthalic anhydride.
  • Juvandol 195 parts of di-pentaerythritol
  • phthalic anhydride 114 parts of phthalic anhydride.
  • Solids content 85%, dissolved in white spirit
  • Viscosity (80% in white spirit): 10 dPa.s
  • An air-drying alkyd resin is prepared from 691 parts of a drying fatty acid, 33 g of para-tertiary-butylbenzoic acid, 185 parts of di-pentaerythritol, 61 parts of isophthalic acid, 32 parts of phthalic anhydride, 32 parts of isophorone diisocyanate and 29 parts of a ketone resin.
  • Solids content 85% by weight in white spirit
  • Viscosity (80% in white spirit / xylene in a ratio of 38: 7):
  • An alkyd resin is prepared from 683 parts of a fatty acid available on the market under the brand name Juvandol fatty acid, 184 parts of pentaerythritol and 201 parts of phthalic anhydride.
  • An alkyd resin is prepared from 783 parts of a semi-drying fatty acid, 177 parts of di-pentaerythritol and 103 parts of phthalic anhydride.
  • Solids content 100% by weight viscosity (80% in white spirit): 2.4 dPa.s
  • a medium-oil alkyd resin is prepared from 496 g of a fatty acid which is available under the brand name Juvandol fatty acid, 229 parts of pentaerythritol, 80 parts of benzoic acid and 272 parts of phthalic anhydride.
  • Fatty acid content 50% by weight acid number: 10 mg KOH / g hydroxyl number: 20 mg KOH / g Solids content: 50% by weight in white spirit and xylene viscosity (50% in xylene): 4.5 dPa.s molecular weight: 88 700
  • An alkyd resin is prepared from 416 parts of a drying fatty acid, 353 parts of di-trimethylolpropane, 66 parts of benzoic acid and 229 parts of phthalic anhydride.
  • Solids content 80% by weight in white spirit and xylene viscosity (50% in xylene): 1.7 dPa.s molecular weight: 6,460
  • An alkyd resin binder is prepared from 595 parts of a drying fatty acid, 243 parts of di-pentaerythritol, 95 parts of benzoic acid and 157 parts of phthalic anhydride.
  • Examples of use of the alkyd resin binders according to the invention are given below. Lacquer formulations are given for the alkyd resins prepared in Examples 2, 3 and 4. In each case, a comparison is made with a known soy alkyd resin which has been prepared without the use of di-pentaerythritol or di-trimethylolpropane (as the alcohol component pentaerythritol). Comparative Example Example a)
  • Silicone oil 0.5 T. 0.5 T.
  • Silicone oil 0.5 T. 0.5 T.
  • the paints produced in Examples a), b) and c) were compared in terms of their drying properties with the paints from the comparative examples. It was found that with the same wet application layer thickness, freedom from dust was achieved after 2 hours (examples) or 1.5 hours (comparative examples). Non-tackiness was achieved after 3.5 hours (examples) and 2.0 hours (comparative examples). The drying through in the examples and the comparative examples was in each case OK after 10 hours.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Paints Or Removers (AREA)

Abstract

On obtient des liants en résine alkyde séchant à l'air à partir de: a) entre 40 et 80 % en poids d'acides gras siccatifs et/ou semi-siccatifs, b) entre 15 et 35 % en poids de diols et/ou polyols, au moins 80 % en poids de ces alcools étant composé de di-pentaérythrite et/ou de di-triméthylolpropane, c) entre 5 et 30 % en poids d'acides dicarboniques et/ou polycarboniques, ou leurs anhydrides, d) entre 0 et 10 % en poids de diisocyanates et e) entre 0 et 20 % en poids d'acides monocarboniques, la somme des constituants a), b), c), d) et e) étant égale à 100 % en poids. L'invention concerne également un procédé de production de ce liant en résine alkyde et d'un enduit à base des résines alkydes décrites. L'enduit a une teneur en matière solide d'au moins 75 % en poids et peut être avantageusement appliqué comme peinture bâtiment séchant à l'air.
EP19870906662 1986-10-30 1987-10-09 Liant en resine alkyde, sechant a l'air, son procede de production, enduit a base de ce liant en resine alkyde et son utilisation comme peinture pour batiments Pending EP0321502A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863636929 DE3636929A1 (de) 1986-10-30 1986-10-30 Lufttrocknende alkydharzbindemittel, verfahren zu ihrer herstellung, ueberzugsmittel auf der basis der alkydharzbindemittel sowie deren verwendung als bautenanstrichmittel
DE3636929 1986-10-30

Publications (1)

Publication Number Publication Date
EP0321502A1 true EP0321502A1 (fr) 1989-06-28

Family

ID=6312801

Family Applications (2)

Application Number Title Priority Date Filing Date
EP87114803A Ceased EP0265746A1 (fr) 1986-10-30 1987-10-09 Liant de résine alkyde séchable à l'air, son procédé de préparation, composition de revêtement à base du liant d'alkyde et son utilisation comme peintures pour bâtiments
EP19870906662 Pending EP0321502A1 (fr) 1986-10-30 1987-10-09 Liant en resine alkyde, sechant a l'air, son procede de production, enduit a base de ce liant en resine alkyde et son utilisation comme peinture pour batiments

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP87114803A Ceased EP0265746A1 (fr) 1986-10-30 1987-10-09 Liant de résine alkyde séchable à l'air, son procédé de préparation, composition de revêtement à base du liant d'alkyde et son utilisation comme peintures pour bâtiments

Country Status (4)

Country Link
EP (2) EP0265746A1 (fr)
BR (1) BR8707847A (fr)
DE (1) DE3636929A1 (fr)
WO (1) WO1988003153A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE460608B (sv) * 1987-06-24 1989-10-30 Bergvik Kemi Ab Bindemedelskomposition foer framstaellning av en lufttorkande lack samt lufttorkande lack
GB2285984B (en) * 1994-01-21 1998-01-28 Ici Plc Environmentally friendly autoxidisable film-forming alkyd coating compositions
DE19841405C2 (de) * 1998-09-10 2000-12-21 Basf Coatings Ag Verfahren zur Herstellung eines thixotropen Bindemittels für Bautenanstrichmittel, thixotrope Bindemittel und Verwendung
AU2001296200A1 (en) * 2000-10-10 2002-04-22 Polymer Coating Technologies Of Singapore Pte Ltd. Low voc polyol alkyd dispersion and polyurethane dispersions
CN100384904C (zh) * 2004-02-10 2008-04-30 方学平 一种用于地板漆的醇酸树脂

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE859952C (de) * 1942-07-09 1952-12-18 Degussa Verfahren zur Herstellung von Kunstharzen
US2459581A (en) * 1944-12-20 1949-01-18 Hercules Powder Co Ltd Resinous mixed esters containing a pentaerythritol
AU467946B2 (en) * 1972-05-09 1975-12-18 Dulux Australia Ltd Novel unsaturated esters
DE3425183A1 (de) * 1984-07-09 1986-01-16 Henkel KGaA, 4000 Düsseldorf Ungesaettigte polyester

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8803153A1 *

Also Published As

Publication number Publication date
WO1988003153A1 (fr) 1988-05-05
DE3636929A1 (de) 1988-05-05
EP0265746A1 (fr) 1988-05-04
BR8707847A (pt) 1989-10-03

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