EP0298968A1 - Wässrige elektrotauchlackbäder für die kathodische elektrotauchlackierung und verfahren zu ihrer herstellung - Google Patents

Wässrige elektrotauchlackbäder für die kathodische elektrotauchlackierung und verfahren zu ihrer herstellung

Info

Publication number
EP0298968A1
EP0298968A1 EP87901476A EP87901476A EP0298968A1 EP 0298968 A1 EP0298968 A1 EP 0298968A1 EP 87901476 A EP87901476 A EP 87901476A EP 87901476 A EP87901476 A EP 87901476A EP 0298968 A1 EP0298968 A1 EP 0298968A1
Authority
EP
European Patent Office
Prior art keywords
reaction
components
amine
neutralized
aqueous
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
EP87901476A
Other languages
German (de)
English (en)
French (fr)
Inventor
Georg SCHÖN
Günter Ott
Michael Geist
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 EP0298968A1 publication Critical patent/EP0298968A1/de
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
    • C09D5/443—Polyepoxides
    • C09D5/4434—Polyepoxides characterised by the nature of the epoxy binder
    • 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
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines

Definitions

  • Aqueous electrocoating baths for cathodic electrocoating and process for their production are provided.
  • the invention relates to aqueous electrodeposition coating baths for cathodic electrodeposition coating, which use modified epoxy as cathodically separable binders.
  • Anina ⁇ ucts contain and have been prepared by 5 (1) (A) polyepoxides and
  • Cationic electrodeposition coating is a coating process that is frequently used primarily for priming, c in which water-thinnable synthetic resins bearing cationic groups are applied to electrically conductive bodies with the aid of direct current. Electrocoating baths of the type described above are disclosed, for example, in the following patent documents:
  • lacquer systems of this type can be used to achieve high-quality lacquers.
  • the electrocoating baths in question undesirably also contain chloride ions, which, if they exceed a concentration limit dependent on several parameters (for example pH value of the electrocoating bath), corrode the electrocoating systems, in particular the anodes (for example pitting corrosion on stainless steel) - electrodes).
  • chloride ions which, if they exceed a concentration limit dependent on several parameters (for example pH value of the electrocoating bath), corrode the electrocoating systems, in particular the anodes (for example pitting corrosion on stainless steel) - electrodes).
  • the disruptive chloride ions mainly come from the polyepoxides used as component (A) for the synthesis of the binders and contaminated with chlorine-containing by-products.
  • the chlorine content of commercially available polyepoxides is between 0.15 and 0.5% due to the presence of such by-products.
  • DE-AS-2751498 describes that the addition of nitrate and / or nitrite ions in the electrocoating bath reduces the corrosion damage caused by the presence of the chloride ions.
  • the object on which the present invention is based is to provide electrodeposition paint baths of the type described at the outset, which have lower chloride ion concentrations than the baths known in the prior art.
  • electrocoating baths of the type described above which are characterized in that the amine-based catalyst which catalyzes the reaction between components (A) and (B) before the further reaction of the components (A) and (B) Intermediates formed with a Bronsted acid, the pK value of the first dissociation stage measured at 20 ° C. which is below 3.7, preferably below 3.5, has been neutralized
  • the invention also relates to a process for the production of aqueous electrocoating baths for cathodic electrocoating, in which
  • reaction products thus obtained are optionally neutralized with acids, dispersed in an aqueous medium and these dispersions are further processed into electrocoating baths using well-known methods characterized in that the reaction between components (A) and (B) is catalytic amine-based catalyst prior to the further reaction of the intermediates formed from components (A) and (B) with a Bronsted acid whose pK value measured at 20 ° C. of the first dissociation stage is below 3.7, preferably below 3.5 lies, is neutralized.
  • the binder which can be deposited by cathodic treatment is produced in a predominantly organic manner by well-known methods
  • components (A) and (B) contain epoxy groups under amine-based catalysis
  • component (A) All compounds whose molecules contain more than 1 epoxy group on average can be used as component (A).
  • Preferred compounds are those which
  • Particularly preferred epoxy compounds are polyglycidyl ethers of polyphenols made from polyphenols and epihalohydrins. Preferred as polyphenol
  • Bisphenol A can be used.
  • Polyglycidyl esters of polycarboxylic acids can also be used. Typical examples are glycidyl adipate and glycidyl phthalate.
  • hydantoin epoxides epoxidized polybutadiene and polyepoxide compounds which are obtained by epoxidizing an olefinically unsaturated alicyclic compound.
  • component (B) which contain one or more, preferably 2, hydroxyl groups per molecule bound to aromatic and / or (cyclo) aliphatic molecular fragments.
  • the compounds which can be considered as component (B) include both low and high molecular weight compounds.
  • Suitable low molecular weight (B) components consist of phenolic, aliphatic and / or alicyclic polyfunctional alcohols with a molecular weight below
  • Examples include:
  • Diols such as ethylene glycol, dipropylene glycol, triglycol,
  • Some preferred diols are 2,2-dimethyl-1,3-propanediol and 3-methyl-1,5-pentanediol.
  • Examples of higher molecular weight (B) components are polyester polyols, polyether polyols or polycaprolactone polyols of different functionality and molecular weights.
  • Polyalkylene ether polyols suitable for component Bj correspond to the general formula:
  • Examples are poly (oxytetra-methylene) glycols and poly (oxyethylene) glycols.
  • the preferred polyalkylene ether polyols are poly (oxytetra-5 methylene) glycols with a molecular weight in the range of 350-1000.
  • Polyester polyols can also be used as (B) components. You can go through the polyester polyols
  • polyesterification of organic polycarboxylic acids or their anhydrides with organic polyols which contain primary 5 hydroxyl groups The polycarboxylic acids and the polyols are usually aliphatic or aromatic dicarboxylic acids and diols.
  • alkylene glycols such as ethylene glycol, butylene glycol,
  • Neopentyl glycol and other glycols such as cyclohexanedimethanol.
  • the acid component of the polyester consists of the first
  • Anhydrides with 2-18 carbon atoms in the molecule are, for example, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, adipic acid, azelaic acid, sebacic acid and glutaric acid.
  • ° are characterized by the presence of a terminal hydroxyl group and by recurring polyester fractions which are derived from the lactone. These recurring molecular parts can be of the formula
  • n is at least 4, preferably 4-6, and the substituent is hydrogen, an alkyl radical
  • all amine-based catalysts can contain one or more basic nitrogen atoms
  • tertiary amines such as e.g. N, N-dimethylbenzylamine, tributylamine, dimethylcyclohexylamine and
  • the amine-based catalyst is generally used in an amount of 0.1-2% by weight, based on the intermediate product formed from components (A) and (B).
  • the a inbasic catalyst can be neutralized before the reaction of components (A) and (B) or in the course of the reaction between components (A) and (B).
  • the amine-based catalyst is switched off within the time interval between the onset of the reaction between components (A) and (B) and the completion of the reaction between components (A) and (B) the epoxy group-containing intermediates formed by components (A) and (B) by adding a sufficient amount neutralized with a suitable Bronsted acid.
  • chloride ion concentrations are achieved which are lower than the chloride ion concentrations to be found in comparable electrodeposition coating baths according to the invention.
  • a particularly preferred embodiment of the invention is that the amine-based catalyst has been neutralized before the reaction of components (A) and (B), i.e. the implementation between the
  • the electrocoating baths produced by the process according to the invention have a chloride ion content which is significantly lower than that found in comparable electrocoating baths, in the manufacture of which the measure according to the invention has not been carried out ... .
  • Brönsted acids are substances that can give off protons.
  • the pK value of the first dissociation stage of the acids used should be below 3.7, preferably below 3.5, very particularly preferably below 3.1. (For a definition of the pK value, see e.g. Organikum, VEB German Publishing House of Sciences, Berlin 1974, page 150 f.)
  • Bronsted acids are benzenesulfonic sulfonic acid, p-toluene sulfonic acid, o-nitrobenzoic acid, salicylic acid and 1Q called phosphoric acid.
  • reaction between components (A) and (B) is preferred at temperatures between 100 and 190 ° C
  • component (C) primary and / or secondary
  • Amines are used, the secondary amines being particularly preferred components (C).
  • the amine should preferably be a water-soluble compound.
  • examples of such amines are mono- and dialkylamines, such as methylamine, ethylamine, propyla in, butylamine,
  • Alkanols such as, for example, are also suitable Methylethanolamine, diethanolamine and the like
  • dialkylaminoalkylamines such as dimethylaminoethylamine, diethylaminopropylamine, dimethylaminopropylamine and the like. suitable.
  • Polyamines with primary and secondary amino groups can be reacted with the epoxy groups in the form of their ketimines.
  • the ketimines are prepared from the polyamines in a known manner.
  • the amines can also contain other groups, but these should not interfere with the reaction of the amine with the epoxy group and should not lead to gelation of the reaction mixture.
  • the charges required for water dilutability and electrical deposition can be protonized with water-soluble acids (e.g. formic acid, lactic acid,
  • the salt of a tertiary amine can be used as the salt of an amine.
  • the amine portion of the amine acid salt is an amine which can be unsubstituted or substituted as in the case of the hydroxylamine, these substituents should not interfere with the reaction of the amine acid salt with the polyepoxide and the reaction mixture should not gel.
  • Preferred amines are tertiary amines, such as dimethylethanolamine, triethylamine, triisopropylamine and the like. Examples of other suitable amines are given in U.S. Patent 3,839,252 at column 5 line 3 through column 7 line 42.
  • the reaction between amines and compounds containing epoxide groups often starts when the reactants are mixed. Depending on the desired course of the reaction - especially to complete the implementation -
  • reaction temperature 50-
  • binders prepared by the process described in detail above are further processed into aqueous electrocoating baths using well-known methods.
  • the electrocoating baths according to the invention can e.g. usual additives such as Crosslinker, coalescing solution
  • agents, pigments, surface-active agents, cross-linking catalysts, antioxidants, fillers, antifoams, etc. contain.
  • electro-dip lacquer baths of the type described above can be provided by a technically very simple process, which compared to comparable dip lacquer baths not produced by the method according to the invention have a lower chloride ion concentration.
  • Epoxy equivalent weight EEW 188, epoxy resin based on bisphenol A from Ciba-Geigy), 151 parts of eopentylglycol and 4.9 parts of dimethylbenzylamine.
  • the temperature is raised to 131 ° C and held until an EEW of 415 is reached.
  • 398 parts of Capa 200 (see Example 4) and a further 3.8 parts of dimethylbenzylamine are added.
  • the temperature is kept at 131 ° C. until an EEW of 1050 is reached.
  • 1274 parts of the crosslinking agent (see Example 4) and 112 parts of the diketi ins also mentioned in Example 4 and 86 parts of N-methylethanolamine are then added and the temperature is kept at 112 ° C. for 1 hour.
  • the low-boiling solvents are then removed in vacuo and a solids content of 35% is established.
  • the argento etrically determined chloride content of this dispersion is 127 ppm chloride.
  • Example 1 is repeated, but 12.5 parts of salicylic acid are added 45 minutes before the EEW of 1030 is reached. The reaction is then terminated as described above.
  • Example 1 is repeated, except that the salt of 4.9 parts of dimethylbenzylamine and 5.3 parts of salicylic acid with the epoxy resin and the neopentyl glycol is initially introduced for catalysis. Likewise, instead of the 3.8 parts
  • the argentometric chloride determination gives a value of less than 55 ppm chloride for these dispersions.
  • Isocyanate crosslinker based on tolylene diisocyanate with butyl glycol capping and reaction with trimethylol propane in a ratio of 3: 1, dissolved in a mixture of MIBK and n-butanol (9: 1) to a solids content of 70%.
  • Emulsifier mixture based on Geigy Amin C (Geigy Industrial Chemicals) 120 parts, Surfynol 104 (Air Products and Chemicals) 120 parts, butylglycol 120 parts and 221 parts deionized water with 19 parts glacial acetic acid.
  • MIBK methyl isobutyl ketone
  • Epikote 829, Capa 200 and xylene are placed in a reaction vessel and placed under N ? - Shielding gas heated to 210 ° C. Water is then removed from the circuit for half an hour. Then the mixture is cooled to 150 ° C. and bisphenol A is added 1 and 1.6 parts of dimethylbenzylamine. The mixture is then heated to 180 ° C. and kept at this temperature for half an hour.
  • n contains deionized water, glacial acetic acid and emulsifier mixture. A vacuum is then applied in order to remove the volatile organic solvents. A solids content of 36% is set.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
EP87901476A 1986-03-26 1987-03-07 Wässrige elektrotauchlackbäder für die kathodische elektrotauchlackierung und verfahren zu ihrer herstellung Pending EP0298968A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3610183 1986-03-26
DE19863610183 DE3610183A1 (de) 1986-03-26 1986-03-26 Waessrige elektrotauchlackbaeder fuer die kathodische elektrotauchlackierung und verfahren zu ihrer herstellung

Publications (1)

Publication Number Publication Date
EP0298968A1 true EP0298968A1 (de) 1989-01-18

Family

ID=6297312

Family Applications (2)

Application Number Title Priority Date Filing Date
EP87103307A Expired - Lifetime EP0238920B1 (de) 1986-03-26 1987-03-07 Wässrige Elektrotauchlackbäder für die kathodische Elektrotauchlackierung und Verfahren zu ihrer Herstellung
EP87901476A Pending EP0298968A1 (de) 1986-03-26 1987-03-07 Wässrige elektrotauchlackbäder für die kathodische elektrotauchlackierung und verfahren zu ihrer herstellung

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP87103307A Expired - Lifetime EP0238920B1 (de) 1986-03-26 1987-03-07 Wässrige Elektrotauchlackbäder für die kathodische Elektrotauchlackierung und Verfahren zu ihrer Herstellung

Country Status (13)

Country Link
US (1) US4944855A (pt)
EP (2) EP0238920B1 (pt)
JP (1) JPH01501943A (pt)
KR (1) KR930007352B1 (pt)
CN (1) CN1009109B (pt)
AT (1) ATE64934T1 (pt)
AU (1) AU595596B2 (pt)
BR (1) BR8707646A (pt)
CA (1) CA1300791C (pt)
DE (2) DE3610183A1 (pt)
ES (1) ES2023374B3 (pt)
WO (1) WO1987005922A1 (pt)
ZA (1) ZA872011B (pt)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63313039A (ja) * 1987-06-15 1988-12-21 Satake Eng Co Ltd 米のアミロ−スまたはアミロペクチンの含有量測定方法およびその装置
DE3801786A1 (de) * 1988-01-22 1989-07-27 Basf Lacke & Farben Verfahren zur beschichtung elektrisch leitfaehiger substrate, nach diesem verfahren beschichtete substrate und waessrige elektrotauchlackbaeder
DE3942766A1 (de) * 1989-12-23 1991-06-27 Basf Lacke & Farben Verfahren zum beschichten elektrisch leitfaehiger substrate, waessriger lack, epoxid-aminaddukt und verwendung des epoxid-aminadduktes als reibharz zur herstellung von pigmentpasten
US6020069A (en) * 1998-06-18 2000-02-01 E. I. Du Pont De Nemours And Company Cathodic electrocoating composition containing an epoxy resin chain extended with a primary amine
CA2300231A1 (en) * 1999-03-10 2000-09-10 Kansai Paint Co., Ltd. Cation-electrodepositable resin composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5144966B2 (pt) * 1972-05-19 1976-12-01
JPS54126239A (en) * 1978-03-25 1979-10-01 Nippon Zeon Co Ltd Cation electrodeposition coating composition
US4419467A (en) * 1981-09-14 1983-12-06 Ppg Industries, Inc. Process for the preparation of cationic resins, aqueous, dispersions, thereof, and electrodeposition using the aqueous dispersions
US4476263A (en) * 1983-11-23 1984-10-09 Scm Corporation Adhesion promoters for sanitary can coatings
DE3409188A1 (de) * 1984-03-14 1985-09-19 Basf Farben + Fasern Ag, 2000 Hamburg Mit alkoholen modifizierte polyepoxide, ihre herstellung und verwendung in haertbaren mischungen
NZ212747A (en) * 1984-07-17 1989-01-27 Dow Chemical Co Partially advanced epoxy resin compositions
US4624975A (en) * 1985-03-21 1986-11-25 The Dow Chemical Company Process for stabilizing the hydrolyzable chloride content in epoxy resins
US4698141A (en) * 1986-07-18 1987-10-06 The Dow Chemical Company Cationic, advanced epoxy resin compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8705922A1 *

Also Published As

Publication number Publication date
CA1300791C (en) 1992-05-12
DE3771097D1 (de) 1991-08-08
JPH01501943A (ja) 1989-07-06
AU595596B2 (en) 1990-04-05
ZA872011B (en) 1987-11-25
DE3610183A1 (de) 1987-10-01
KR880701268A (ko) 1988-07-26
BR8707646A (pt) 1989-03-14
JPH0357154B2 (pt) 1991-08-30
EP0238920A1 (de) 1987-09-30
US4944855A (en) 1990-07-31
CN1009109B (zh) 1990-08-08
WO1987005922A1 (en) 1987-10-08
CN87102278A (zh) 1988-02-24
ATE64934T1 (de) 1991-07-15
EP0238920B1 (de) 1991-07-03
AU7125287A (en) 1987-10-20
KR930007352B1 (ko) 1993-08-09
ES2023374B3 (es) 1992-01-16

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