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WO1996001292A1 - Procede de fabrication d'une dispersion non aqueuse, steriquement stabilisee, d'un polyepoxy, et agent de revêtement renfermant cette dispersion - Google Patents

Procede de fabrication d'une dispersion non aqueuse, steriquement stabilisee, d'un polyepoxy, et agent de revêtement renfermant cette dispersion Download PDF

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Publication number
WO1996001292A1
WO1996001292A1 PCT/EP1995/002531 EP9502531W WO9601292A1 WO 1996001292 A1 WO1996001292 A1 WO 1996001292A1 EP 9502531 W EP9502531 W EP 9502531W WO 9601292 A1 WO9601292 A1 WO 9601292A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy resin
component
dispersion
stage
diol
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/EP1995/002531
Other languages
German (de)
English (en)
Inventor
Lazaros Vogdanis
Klaus Cibura
Wolfgang Bremser
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
Priority to JP8503665A priority Critical patent/JPH10502403A/ja
Priority to EP95925787A priority patent/EP0769037A1/fr
Priority to AU29788/95A priority patent/AU693915B2/en
Priority to BR9508204A priority patent/BR9508204A/pt
Publication of WO1996001292A1 publication Critical patent/WO1996001292A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Definitions

  • the present application relates to a process for the preparation of a sterically stabilized, nonaqueous dispersion of a polyepoxide, in which in an organic solvent in the presence of a dispersion stabilizer at least one epoxy resin (A) with on average at least 2 epoxy groups per molecule with min ⁇ at least one diol (B) of the formula (I)
  • D is a methylene or a propylene group, and optionally with a further component (C) which has groups which are reactive toward epoxy or hydroxyl groups.
  • the present invention also relates to the non-aqueous dispersions prepared by this process and to the use of these dispersions in coating compositions, in particular for the coating of packaging.
  • EP-A-321 088 discloses a method for producing a sterically stabilized, non-aqueous dispersion of a polyepoxide according to the preamble of claim 1.
  • the only disadvantage of this method is limited possible production of dispersions with a defined structure.
  • the need for improvement in this process is the incorporation of additional resins.
  • various mechanical properties of the resulting coatings also need to be improved.
  • the present invention is therefore based on the object of providing a method for producing a sterically stabilized, non-aqueous dispersion of a poly epoxide, in which the resulting dispersions have a defined structure. Furthermore, the dispersions should have a good incorporability / carrying capacity for one or more other resins. Furthermore, the resulting dispersions, when used as coating compositions for the interior painting of cans, should meet the requirements normally placed on these coating compositions, e.g. good adhesion and good flexibility, good sterilization resistance and freedom from pores in the resulting coatings and good application properties of the coating compositions. In addition, the process should be simple and inexpensive to carry out.
  • the present invention also relates to the non-aqueous dispersions prepared by this process and the use of these dispersions in coating compositions, in particular for the coating of packaging.
  • the process according to the invention has the surprising advantage that the incorporation of further resins into the dispersions is improved. It is also advantageous that dispersions of resins with a defined structure are obtained with the process according to the invention. The flexibility, adhesion and resistance to sterilization of the resulting coatings are also improved. Finally, it is advantageous that the resulting dispersions, when used in coating compositions for the interior painting of cans, meet the requirements usually placed on these coating compositions, e.g. B. good application properties of the coating compositions.
  • R is a group of the formula (II)
  • Bisphenol A is preferably used as the diol (B) of the formula (I).
  • Epoxy resins (A) suitable for producing the non-aqueous dispersion of the polyepoxide according to the invention are, in particular for stage (1) of the process, epoxides with an average of at least 2 epoxy groups per molecule. Epoxy resins which are liquid at room temperature are preferably used as component (A). Epoxy resins with an epoxide equivalent weight of 150 to 450, preferably 170 to 192, are particularly preferably used.
  • Aromatic epoxy resins (A) are particularly suitable for use in the process according to the invention, but aliphatic and araliphatic epoxy resins (A) are also suitable. Examples include diglycidyl ethers of polyphenols, diglycidyl ethers of dialcohols and diglycidyl esters of dicarboxylic acids. Diglycidyl ethers of polyphenols, in particular diglycidyl ethers of bisphenol A, and epoxidized novolak resins, particularly preferably epoxy resins based on bisphenol A, are used. Mixtures of different epoxy resins can of course also be used. Furthermore, it is of course also possible to use different epoxy resins (A) in stage (1) and stage (2) of the process according to the invention. In particular, it is also possible to use epoxy resins (A) in stage (2) of the process according to the invention a functionality ⁇ 2, for example also monoepoxides.
  • Suitable epoxy resins (A) are, for example, the products commercially available under the following names
  • GY 250 from Ciba-Geigy.
  • small amounts, preferably less than 20% by weight, particularly preferably from 1 to 15% by weight, of the diol (B) and / or the epoxy resin component (A) can be replaced by other components (C) which are associated with the epoxy resin component (A) or with the reaction product obtained in stage (1) of the process.
  • functional compounds are used as component (C).
  • reaction of the diol (B) of the formula (I) and optionally of the component (C) with the epoxy resin component (A) takes place in the presence of a steric dispersion stabilizer.
  • a steric dispersion stabilizer is a compound with a part which is associated with the epoxy resin to be stabilized (usually referred to as anchor component) and a part which is associated with the solvent (usually referred to as a solvated component).
  • Suitable steric dispersion stabilizers are known and are described, for example, in EP-A-321 088 on page 5, line 41, to page 6, line 1, and in K.E.J. Barrett, Dispersion Polymerization in Organic Media, John Wiley and Sons, 1975.
  • Suitable acrylate polymers are homopolymers and copolymers of (meth) acrylic acid alkyl esters (for example polymethyl methacrylate, polyethyl methacrylate, polymethyl acrylate, polyethyl acrylate, polyethyl acrylate / polyethyl methacrylate, etc.) and copolymers of (meth) acrylic acid alkyl esters and methacrylic acid and / or acrylic acid, where The proportion of polymerized (meth) acrylic acid is usually below 10% by weight.
  • small amounts of other ethylenically unsaturated monomers can be polymerized into the copolymers, for example small amounts of crotonic acid, isocrotonic acid, maleic acid and / or alkyl esters of these acids.
  • the solvated component can be a poly-C6-18 alkyl ester, e.g. Poly-2-ethylhexyl acrylate, a
  • Polyester such as Poly-12-hydroxystearic acid, or a polymer, e.g. resins derived from polybutadiene.
  • the dispersion stabilizers can be prepared by the customarily used methods, for example by copolymerizing the reaction product of poly-12-hydroxystearic acid with glycidyl (meth) acrylate with the desired acrylate monomers or, for example, by polymerizing the desired anchor component with the solvated component desired polymer (for example derived from polybutadiene) is implemented.
  • Solvents which do not dissolve the resulting polyepoxide are used in particular in the process according to the invention.
  • Aliphatic hydrocarbons are preferably used as solvents, which may also contain up to 20% by weight of other solvents, e.g. aromatic hydrocarbons, e.g. Xylene and Solvesso® 150 may contain.
  • High-boiling aliphatic hydrocarbons are preferably used as solvents.
  • suitable solvents are Hydrosol® P 2300 EA from Deutsche Hydrocarbures GmbH, Exxold® 240-270, Norpar® 12 and Isopar® M from Deutsche Exxon Chemical GmbH.
  • the amount of solvent is preferably selected so that the reaction of the diol (B) with the epoxy resin component (A) (stage (1)) at a dispersion solids content of 20 to 80% by weight, preferably 50 to 70% Wt .-% and the implementation of the reaction product
  • Step (1) with the diol (B) (step (2)) is carried out at a dispersion solids content of 25 to 85% by weight, preferably 55 to 75% by weight.
  • the reaction of the diol (B) with the epoxy resin component (A) is preferably carried out in the presence of a catalyst.
  • Suitable catalysts are, for example, alkali metal carbonates, such as potassium and sodium carbonate, alkali metal hydroxides, such as sodium and potassium hydroxide, quaternary ammonium salts, amines, such as dibenzylamine, and trialkylphosphonium salts, such as e.g. Triphenylethylphosphonium iodide and triphenylethylphosphonium acetate. Triphenylethylphosphonium iodide is preferably used as the catalyst.
  • reaction products produced by the process according to the invention usually have an equivalent weight of functional groups from 678 to infinity, preferably of more than 1000. If the reaction product of the first stage is reacted exclusively or predominantly with a diepoxide (A) in the second stage of the process, the polyepoxide resins prepared by the process according to the invention have epoxide groups as functional groups (epoxide equivalent weight is specified). If, on the other hand, the reaction product of the first stage is reacted in the second stage with a monoepoxide and / or component (C), the equivalent important the content of functional groups which are introduced into the resin by these components.
  • A diepoxide
  • C monoepoxide and / or component
  • part of the epoxy resin component (A) is first mixed with an excess of at least one diol (B) of the formula (I) and, if appropriate, component (C), based on those in this stage (1) of the process amount of epoxy resin component (A) used.
  • An essentially phenoxy-terminated product is obtained.
  • the amounts of epoxy resin component (A) and diol (B) of the formula (I) are preferably chosen so that 1 ol epoxy resin component with 3 to 1.001 mol, preferably 1.5 to 1.02 mol, of at least one diol (B), is implemented.
  • the reaction of the epoxy resin component (A) with the diol (s) (B) and optionally (C) in the first stage of the process according to the invention is preferably carried out in that the epoxy resin or diols and the diols and optionally (C) the dispersion stabilizer and the solvent are combined and slowly heated with stirring. It is preferably heated to temperatures between 80 and 140 ° C. At this slightly elevated temperature, it is preferred to disperse for some time first. Thereafter, the catalyst is added if necessary and heated to the desired reaction temperature.
  • the reaction of the epoxy resin with the diol and optionally (C) is usually carried out at a temperature between 120 and 250 ° C., preferably at a temperature between 160 and 180 ° C.
  • the first stage of the process according to the invention it is also possible to initially introduce the epoxy resin component (A) with the solvent and the dispersion stabilizer and by stirring and, if appropriate, slightly heating, preferably to temperatures between 80 and 140 ° C to disperse the epoxy resin component.
  • the dispersion can then be heated to the desired reaction temperature and the diol (B) and optionally (C) added.
  • the reaction of the epoxy resin component (A) with the diol (s) (B) is preferably continued in the first stage of the process until the resulting reaction product has a phenoxy equivalent weight of at least 256, preferably at least 682 and particularly preferably at most 20,000. having.
  • the phenoxy-terminated reaction product obtained in stage (1) is then reacted with the remaining epoxy resin component (A) and / or possibly further modifying components to give the desired end product.
  • the product obtained in stage (1) is preferably reacted with the remaining epoxy resin component (A).
  • the reaction with the remaining epoxy resin component and / or possibly further modifying components (C) is preferably carried out in that the epoxy resin and possibly the further modifying components are slowly added at an elevated temperature, preferably at a temperature of 60 to 120 ° C be dropped. It is also possible to add the remaining epoxy resin component in step 2 of the process all at once. After the addition of the epoxy resin or the addition of the modifying components, catalyst is preferably added again and the temperature is increased, preferably to values between 160 and 180 ° C. Then the reaction is continued until the desired degree of conversion is reached.
  • the dispersions of polyepoxy resins produced by the process according to the invention are particularly suitable for use in coating compositions.
  • these coating compositions can also contain further binding agents, further customary solvents, optionally further resins, optionally pigments and / or fillers and customary auxiliaries and additives in customary amounts.
  • the coating compositions preferably contain up to 100% by weight, particularly preferably 60 to 100% by weight, of the non-aqueous dispersion, 0 to 40% by weight of further binders, 0 to 40% by weight of further resins, 30 to 80% by weight of solvent (including the solvent content of the non-aqueous dispersion), 0 to 50% by weight of pigments and / or fillers and 0 to 10% by weight of conventional auxiliaries and additives, in each case based on the total weight of the coating agent.
  • the coating compositions are preferably used for coating packaging, in particular for coating food packaging.
  • the packaging can come from a wide variety Materials exist and have a wide variety of geometries.
  • the materials in particular are black sheet, tinplate and various iron alloys, which may be provided with a passivation layer based on nickel, chromium and zinc compounds.
  • the packaging can be coated in the form of, for example, half-can parts, that is to say hulls and lids, as 3-part cans and as 2-part, deep-drawn or otherwise deep-drawn cans, such as, for example, beverage and food cans.
  • the coating compositions according to the invention cure in the object temperature range from 150 to 400 ° C. for a period of from 2 s to 15 min. They can be applied by rolling, knife coating, brushing, spraying, flooding or dipping by means of conventional devices, the film then being cured to form a firmly adhering coating.
  • the coating compositions are preferably applied by roller application.
  • feed 1 and feed 2 are metered in simultaneously, but separately, within 1.5 h
  • the solution of the dispersion stabilizer thus obtained has a solids content (60 min 130 ° C.) of 38.5%, an acid number of 21 mgKOH / g and a viscosity of 2.2 + 0.2 dPa.s (ICI plate / cone viscometer , 23 ° C).
  • stage II The mixture is then dispersed for one hour. Then be
  • the dispersion obtained has a solids content (90 min 180 ⁇ C) of 63.5% and a viscosity (ICI plate / cone viscometer, 23 ⁇ C) of 2.9 dPa.s.
  • the polyepoxide obtained has a number-average molecule Lar weight of 11 375, a weight average molecular weight of 78 069 and a non-uniformity of 6.9 (each determined by gel permeation chromatography against polystyrene standard).
  • the dispersion obtained in this way has a shelf life of more than 30 days at 23 ° C.
  • the dispersion obtained has a solids content (90 min 180 ° C.) of 60.3%.
  • the polyepoxide obtained has a number average molecular weight of 10,305, a weight average molecular weight of 43,609 and a non-uniformity of 4.2 (in each case determined by gel permeation chromatography against the polystyrene standard).
  • the dispersion thus obtained has a

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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)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention a pour objet un procédé de fabrication d'une dispersion non aqueuse, stériquement stabilisée, d'un polyépoxy, consistant à faire réagir dans un solvant organique, en présence d'un stabilisateur de dispersion, au moins une résine époxy (A) ayant au moins deux groupes époxy, avec au moins un diol (B) de formule (I) HOROH, dans laquelle R est un groupe de formule (II), où D désigne un groupe méthylène ou un groupe propylène et, le cas échéant, avec un autre composant (C) présentant des groupes capables de réagir avec des groupes époxy ou hydroxyle, caractérisé en ce que 1) dans une première étape, une partie de composant résine époxy (A) est mis à réagir avec un excès, par rapport à la quantité de résine époxy utilisée à cette étape (1), du diol (B) de formule (I) et, le cas échéant, du composant (C), et en ce que 2) le produit provenant de la réaction, obtenu à l'étape (1) est ensuite mis à réagir avec le reste de résine époxy (A) et/ou du composant (C), de manière à obtenir le produit final voulu.
PCT/EP1995/002531 1994-07-02 1995-06-29 Procede de fabrication d'une dispersion non aqueuse, steriquement stabilisee, d'un polyepoxy, et agent de revêtement renfermant cette dispersion Ceased WO1996001292A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP8503665A JPH10502403A (ja) 1994-07-02 1995-06-29 滅菌安定化されたポリエポキシド非水性分散液の製造法および該分散液を含有する被覆剤
EP95925787A EP0769037A1 (fr) 1994-07-02 1995-06-29 Procede de fabrication d'une dispersion non aqueuse, steriquement stabilisee, d'un polyepoxy, et agent de rev tement renfermant cette dispersion
AU29788/95A AU693915B2 (en) 1994-07-02 1995-06-29 Method of producing a sterically stabilized non-aqueous dispersion of a polyepoxide, and coating materials containing such a dispersion
BR9508204A BR9508204A (pt) 1994-07-02 1995-06-29 Processo para a preparação de uma dispersão não-aquosa estericamente estabilizada de um poliepóxido e composições de revestimento que contêm essa dispersão

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4423309.4 1994-07-02
DE4423309A DE4423309A1 (de) 1994-07-02 1994-07-02 Verfahren zur Herstellung einer sterisch stabilisierten, nichtwäßrigen Dispersion eines Polyepoxids und diese Dispersion enthaltende Beschichtungsmittel

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/065,492 Continuation-In-Part US6344217B1 (en) 1994-06-28 1998-04-24 Putamen OVI

Publications (1)

Publication Number Publication Date
WO1996001292A1 true WO1996001292A1 (fr) 1996-01-18

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/002531 Ceased WO1996001292A1 (fr) 1994-07-02 1995-06-29 Procede de fabrication d'une dispersion non aqueuse, steriquement stabilisee, d'un polyepoxy, et agent de revêtement renfermant cette dispersion

Country Status (8)

Country Link
EP (1) EP0769037A1 (fr)
JP (1) JPH10502403A (fr)
AU (1) AU693915B2 (fr)
BR (1) BR9508204A (fr)
CA (1) CA2189864A1 (fr)
DE (1) DE4423309A1 (fr)
TR (1) TR199500792A2 (fr)
WO (1) WO1996001292A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19607435A1 (de) * 1996-02-28 1997-09-04 Basf Lacke & Farben Sterisch stabilisierte, nicht-wäßrige Dispersion, und Beschichtungsmittel auf deren Basis
EP3124515A1 (fr) 2015-07-28 2017-02-01 Evonik Degussa GmbH Dispersions reactives non aqueuses pour peintures, materiaux d'etancheite et adhesifs

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4568735A (en) * 1984-11-05 1986-02-04 Shell Oil Company Process for preparing polyepoxides (II)
JPS6173726A (ja) * 1984-09-19 1986-04-15 Nippon Oil & Fats Co Ltd 非水系エポキシ樹脂分散体の製造方法
WO1986004902A1 (fr) * 1985-02-26 1986-08-28 The Dow Chemical Company Dispersions non-aqueuses de resines epoxydes a poids moleculaire relativement eleve
EP0321088A2 (fr) * 1987-12-04 1989-06-21 Imperial Chemical Industries Plc Procédé pour préparer des dispersions de résines époxyde allongées
WO1993004104A1 (fr) * 1991-08-26 1993-03-04 The Dow Chemical Company Compositions de resines epoxy evoluees flexibilisees de l'interieur et revetements produits a base de ces compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6173726A (ja) * 1984-09-19 1986-04-15 Nippon Oil & Fats Co Ltd 非水系エポキシ樹脂分散体の製造方法
US4568735A (en) * 1984-11-05 1986-02-04 Shell Oil Company Process for preparing polyepoxides (II)
WO1986004902A1 (fr) * 1985-02-26 1986-08-28 The Dow Chemical Company Dispersions non-aqueuses de resines epoxydes a poids moleculaire relativement eleve
EP0321088A2 (fr) * 1987-12-04 1989-06-21 Imperial Chemical Industries Plc Procédé pour préparer des dispersions de résines époxyde allongées
WO1993004104A1 (fr) * 1991-08-26 1993-03-04 The Dow Chemical Company Compositions de resines epoxy evoluees flexibilisees de l'interieur et revetements produits a base de ces compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; AN 86-135556(21) *

Also Published As

Publication number Publication date
DE4423309A1 (de) 1996-01-04
EP0769037A1 (fr) 1997-04-23
JPH10502403A (ja) 1998-03-03
TR199500792A2 (tr) 1996-06-21
AU2978895A (en) 1996-01-25
CA2189864A1 (fr) 1996-01-18
AU693915B2 (en) 1998-07-09
BR9508204A (pt) 1997-12-23

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