EP0327589A1 - Compositions de revetement diluables dans l'eau pour fabrication de revetements thermodurcissables - Google Patents
Compositions de revetement diluables dans l'eau pour fabrication de revetements thermodurcissablesInfo
- Publication number
- EP0327589A1 EP0327589A1 EP87907751A EP87907751A EP0327589A1 EP 0327589 A1 EP0327589 A1 EP 0327589A1 EP 87907751 A EP87907751 A EP 87907751A EP 87907751 A EP87907751 A EP 87907751A EP 0327589 A1 EP0327589 A1 EP 0327589A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyester
- epoxy
- acid
- water
- carboxyl groups
- 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.)
- Withdrawn
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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- 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
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Definitions
- thermosetting coatings for the production of thermosetting coatings
- the invention relates to water-thinnable coating compositions for the production of thermosetting coatings, the binders of which at least partially consist of an epoxy-modified, water-thinnable polyester.
- a primer is usually applied first, then a filler and finally the top coat.
- the filler layer is applied with the aid of preferably electrostatic spraying processes.
- electrostatic spraying processes considerable savings in material, combined with a high degree of automation, are achieved compared to other spraying processes.
- the filler material has good application behavior, i.e. good sprayability in preferably electrostatic or electrostatically assisted spraying processes, favorable theological properties, good spray mist absorption and favorable drying behavior.
- One of the tasks of the filler is to fill in and cover any unevenness in order to level the surface for the subsequent topcoat. This coverage of underground Structures and substrate defects must be managed without extensive grinding work being carried out on the filler layer; a requirement that can only be met if the filler material shows good flow properties.
- the object of the invention is to develop water-thinnable coating compositions for the production of heat-curable coatings which show the application properties required for use in automotive serial painting and which provide coatings which are as good or even better than 25 in their properties the coatings which have been produced using conventional filler materials containing organic solvents.
- water-thinnable coating compositions the binders of which at least partially consist of an epoxy-modified, water-thinnable polyester which has been prepared by (A) from o o o cr (ai) at least one at least three carboxyl groups containing polycarboxylic acid or a reactive derivative of this acid and / or (a ? ) at least one polyol having at least one carboxyl group and (a ⁇ ) at least one polycarboxylic acid containing two carboxyl groups or a reactive derivative of this acid and
- At least 10 mol%, preferably 30-70 mol%, of the components used (a ..), (a 2 ), (a 3 ) and (a 4 ) (based on (a ⁇ ) + (a ⁇ ) + (a 3 ) + (a 4 ) 10 ° mol%) contain at least one (cyclo) aliphatic structural element having at least six carbon atoms - a polyester has been synthesized which has an average molecular weight (number average) of less than 2000, preferably 500 to 1500, an acid number of 35 to 240, preferably 50 to 120, an OH number of 56 to -320, preferably 80 to 200, and in which all (a _.) and (a ") components over at least two carboxyl groups are condensed in and (B) this polyester obtained in this way is then used with 0.3 to 1.5, preferably 0.5 to 1.0 equivalents per polyester molecule having an epoxy equivalent weight of 170 to 1000, preferably 170 to 500 , Epoxy resin based on a bis
- the carboxyl groups of the polyester are supplied by components (a) and / or (a 2 ).
- the polyester can be used using only the carboxyl group suppliers (a-) or (a ? ) Or using a mixture of the
- any component suitable for the production of polyesters and containing at least three carboxyl groups or a reactive derivative (for example anhydride, ester or halide) or a mixture of such acids or acid derivatives can be used as component (a 1 ), taking into account the above-mentioned requirements become.
- a 1 any component suitable for the production of polyesters and containing at least three carboxyl groups or a reactive derivative (for example anhydride, ester or halide) or a mixture of such acids or acid derivatives
- component (a 1 ) examples include trimellitic acid, trimesic acid (1,3,5-benzenetricarboxylic acid), pyromellitic acid and trimeric fatty acids. Trimellitic acid is preferably used.
- Component (a 2 ) can in principle be any carboxyl-containing polyol or a mixture of such polyols suitable for the production of polyesters, taking into account the above-mentioned requirements, a polyol being understood to mean an organic compound which carries at least two hydroxyl groups ⁇ Dimethylolpropionic acid is used as (a ") component.
- component (a) in principle, any polycarboxylic acid containing two carboxyl groups or a reactive derivative (eg anhydride, ester or halide) or a mixture of such acids or acid derivatives suitable for the preparation of polyesters or a mixture of such acids or acid derivatives can be used.
- Suitable acids include: phthalic acid, isophthalic acid, terephthalic acid, fumaric acid, maleic acid, endomethylene tetrahydrophthalic acid, succinic acid, adipic acid, corkic acid,fuginic acid, sebacic acid and dimeric fatty acids. Phthalic acid, isophthalic acid, adipic acid and dimeric acids are preferred.
- Component (a 4 ) can in principle be any polyol or a mixture of polyols suitable for the production of polyesters, taking into account the above-mentioned requirements, polyol being understood as an organic compound which carries at least 2 hydroxyl groups.
- Suitable polyols are, for example, ethylene glycol, propanediols, butanediols, pentanediols, neopentyl glycol, hexanediols, diethylene glycol, glycerol, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol, hydroxypivalic acid neopentylglycol ester, 2-methyl-2-propyl, propyl-2-propyl 2,2,4-trimethylpentanediol-1, 3 and 2,2,5-trimethylhexanediol-1,6.
- Neopentyl glycol, 1,6-hexanediol and hydroxypivalic acid neopentyl glycol esters are preferably used.
- the polyester produced from components (a.) And / or (a 2 ), (a 3 ) and (a 4 ) with the above-mentioned characteristics is 0.3 to 1.5, preferably 0.5 to 1.0 equivalents per polyester molecule of an epoxy resin having an epoxy equivalent weight of 170 to 1000, preferably 170 to 500, epoxy resin based on a bisphenol, preferably bisphenol A, and / or a derivative of this epoxy resin containing at least one epoxy group per molecule under reaction conditions in which essentially only Carboxyl groups react with epoxy groups to form an inventive one implemented epoxy resin-modified polyester which, after neutralization of at least some of the free carboxyl groups, is present in water-dilutable form.
- the epoxy resins based on a bisphenol, preferably bisphenol A, are generally reaction products of bisphenols with epichlorohydrin. These epoxy resins should have an epoxy equivalent weight of 170 to 1000, preferably 170 to 500, and preferably contain on average one to two, particularly preferably two, epoxy groups per molecule.
- Suitable derivatives can be at least one epoxide group per molecule having reaction products of the above-mentioned epoxy resins and a (cyclo) aliphatic mono- or polycarboxylic acid, preferably a mono- or polycarboxylic acid with a (cyclo) aliphatic having at least 6 carbon atoms Structural element can be used.
- the derivatives can be prepared by reacting the epoxy resins in question, for example, with polymeric, preferably dimeric, fatty acids, adipic acid, azelaic acid, dodecanedicarboxylic acid, long-chain monocarboxylic acids, tetrahydrophthalic acid or hexahydrophthalic acid in such a way that reaction products are formed which still contain at least one Contain epoxy group per molecule.
- Very particularly preferred water-dilutable coating compositions are obtained if the polyester synthesized in step (A) contains 0.3 to 1.5, preferably 0.5 to 1.0 equivalents per polyester molecule of a reaction product having at least one epoxy group per molecule product of an epoxy resin based on a bisphenol, preferably bisphenol A, with an epoxy equivalent weight of 170 to 1000, preferably 170 to 500, and a (cyclo-) aliphatic mono- or polycarboxylic acid with an independent at least 18 carbon atoms (cyclo) aliphatic structural element, preferably a polymeric, in particular a dimeric, fatty acid.
- step (A) The reaction between the polyester synthesized in step (A) with the epoxy resin or epoxy resin derivative must be carried out in such a way that essentially only the carboxyl groups of the polyester are reacted with the epoxy groups of the epoxy resin and that competitive reactions, such as e.g. The reaction of hydroxyl groups with epoxy groups only take place to a minor extent.
- Suitable reaction conditions include: reaction temperature 25-180 C, preferably 80-160 C.
- the reaction can be carried out in an internal solvent or in bulk and is advantageously carried out using basic catalysts, such as e.g. tertiary amines, catalyzed.
- the epoxy resin-modified polyester according to the invention After neutralization of at least some of the carboxyl groups contained in the epoxy resin-modified polyester according to the invention with basic compounds, such as e.g. Ammonia, aliphatic secondary and tertiary amines, such as diisopropanol in, dimethyl and diethylaminoethanol and trimethyl, triethyl and tripropylamine, preferably tertiary amines, the epoxy resin-modified polyester according to the invention is in water-dilutable form.
- basic compounds such as e.g. Ammonia, aliphatic secondary and tertiary amines, such as diisopropanol in, dimethyl and diethylaminoethanol and trimethyl, triethyl and tripropylamine, preferably tertiary amines
- Epoxy resin-modified polyesters of the invention, crosslinkers are tongues for preparing the Kochzugszusammenset- invention (for example, amino resins, 'particularly those of the type hexamethoxymethylmelamine, urea resins, epoxy resins wasserver ⁇ dilutable udgl.), Optionally further binders, pigments, fillers and other customary additives to a water-dilutable Processed coating composition.
- the water-dilutable coating compositions according to the invention can also be used in subordinate Dimensions contain solvent as a diluent.
- polyesters according to the invention are their good compatibility with the other coating components, in particular with crosslinking agents and other binders which may be present in the coating composition.
- the coating compositions according to the invention contain the polyester according to the invention as the sole binder; this embodiment is made possible by the fact that the polyester according to the invention can also be used as a rubbing resin due to its excellent pigment wetting properties.
- the coating compositions according to the invention show excellent application properties even in the case of fluctuating air humidity values and are well suited for use in series coating. They can be processed particularly well with electrostatic or electrostatically assisted spraying processes, show favorable theological properties, good spray mist absorption, good flow properties, favorable drying behavior and good wetting behavior compared to PVC.
- the baked layers obtained with the aid of the coating compositions according to the invention show a lower tendency to yellowing and optimum intermediate adhesion properties in comparison with known systems. Together with the primer and the topcoat layer or layers, they lead to coatings with a very good Topcoat level and excellent resistance to stone chips and other mechanical attacks, even at very high and very low temperatures.
- Suitable substrates can, for example, be made of ceramic, glass, concrete, plastic, preferably metal such as iron, zinc, copper, aluminum, steel and the like. consist.
- coatings can be obtained which have a particularly high gloss.
- coating compositions according to the invention provide coatings which adhere excellently to the optionally pretreated substrates and show very good resistance values to mechanical attacks and organic solvents.
- the temperature of the reaction mixture is increased so slowly while distilling off the condensation water up to a maximum of 220 ° C that the vapor temperature at the top of the column does not exceed 103 ° C. increases. It is condensed at 220 C until the reaction material has reached an acid number of 10.5. After cooling to 140 ° C., 266.7 g of trimellitic anhydride are added in portions to the reaction mixture with stirring. The mixture is then heated to 150 ° C. and esterified until the reaction mixture has reached an acid number of 67.7. The mixture is then cooled to 120 ° C.
- a P Prroobbee diluted to 50% by weight with ethylene glycol monobutyl ether at the same time has an amount of 420 mPa's (23 C ICI plate-cone viscometer)
- the 85% polyester solution is heated to 140 ° C. and 209.6 g of an epoxy resin composed of bisphenol-A and epichlorohydrin with an epoxy equivalent weight of 490 are added in portions with stirring. The reaction is then continued at 140 ° C. until an epoxy equivalent weight of more than 50,000 and an acid number of 42.1 (based on solids) have been reached. It is then cooled to 100 ° C. and neutralized with 64.6 g of N, N-dimethylethanolamine.
- reaction mixture is then discharged with stirring into 2,000 g of deionized water which has been heated to 60 ° C., and a stable binder dispersion is produced by intensive stirring, which is applied to a solid with 180 g of deionized water and N, N-dimethylethanolamine of 35% by weight (determined after drying for 60 minutes at 130 ° C in a forced-air drying cabinet) and a pressure at 23 ° C of 6.67. »
- polyester A From the polyester produced in the first stage of the preparation of polyester A, 1,110 g of a 90% by weight solution in ethylene glycol monobutyl ether are prepared and mixed with 270 g of the epoxy resin solution prepared by the process described above. The mixture is on
- Deionized water and N, N-dimethylethanolamine are added to the aqueous polyester dispersions obtained in accordance with the above-described regulations, in accordance with the weight ratios given in Table 1, pasted with post-treated titanium dioxide of the rutile type and mixed with an unsaturated branched diol as an anti-foaming agent. These mixtures are filled in a discontinuous laboratory sand mill and dispersed until a fineness by Max. 10 ⁇ m, measured in a Hegmann grindometer, is achieved.
- the coating compositions 1, 2, 3 and 4 according to the invention are then obtained from the dispersing mixtures with the addition of further polyester dispersion, low molecular weight melamine resin, highly etherified with methanol, ethylene glycol ethers, water-dilutable acrylate resin as leveling agent and deionized water (cf. Table 1).
- the coating compositions prepared in accordance with the above-described regulations were adjusted to a viscosity of 25 s with deionized water, measured in a discharge cup according to DIN 4 at 20 ° C., and in with a flow cup gun (nozzle opening 1.2 mm; air pressure 4.5 bar) two cloisters with 1 minute flash-off time sprayed onto phosphated steel sheets.
- the application was carried out at an air temperature of 23 C and a relative humidity of 60%.
- the sprayed panels were flashed off in a forced air oven for 10 minutes at 23 ° C. and 10 minutes at 80 ° C. and then baked in a forced air oven for 20 minutes at 160 ° C., cooled and assessed.
- the coating compositions prepared according to the above-described regulations were also applied electrostatically.
- An Esta-Behr system with a bell TOS 300/5/8, a distance of 30 cm and a speed of 30,000 revolutions per minute was used at a relative humidity of 40-70%.
- the coating compositions 1 to 4 according to the invention were sprayed onto the phosphated steel sheets coated with an electrodeposition paint according to Example 6 of DE-0S-2701002 by the process set out above.
- the coatings obtained showed a very good flow, covered the structure of the electrocoating very well and showed good intermediate adhesion to the electrocoating primer (cf. Table 3).
- the coating compositions of the invention were applied to baked steel sheets as described above and baked. After cooling, the panels were then additionally coated with a solvent-based white baking topcoat based on an alkyd resin with saturated and unsaturated fatty acids (acid number 12, OH number 110) in combination with a medium molecular weight melamine resin, partially etherified with n-butanol (ratio 2: 1), pigmented with a post-treated titanium dioxide of the rutile type (PVC 21%) and with solvents and additives, which are usually used for the processing of a paint for automotive serial painting, sprayed over and baked at 130 C for 30 min (dry film thickness
- the coatings are characterized by good flow, good coverage of the structure of the primer and good intermediate adhesion (cf. Tab. 4). Table 1
- Antifoam (50% solution in ethylene glycol monobutyl ether) 0.3 0.3 0.3 0.3 0.3 0.3
- Leveling agent (50% solution in ethylene glycol monobutyl ether) 1.0 1.0 1.0 1.0 1.0 1.0 deionized water 0.9 5.6 0.9 5.6 100.0 100.0 100.0 100.0 100.0 100.0
- the stone chip test was carried out with a VDA stone chip testing device (model 508) (one-off bombardment within 20 s with 1000 g of steel shot; pressure 2 bar).
- the rating scale ranges from 1 (very good) to 10 (very bad).
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Epoxy Resins (AREA)
Abstract
Dans les compositions décrites, le liant est constitué au moins en partie d'un polyester diluable dans l'eau et modifié par une résine époxy. Lesdites compositions sont caractérisées en ce que l'on produit le polyester précité (A) en faisant la synthèse d'un polyester à partir de (a1) au moins un acide polycarboxylique contenant au moins trois groupes carboxyle ou bien d'un dérivé réactif de cet acide et/ou (a2) au moins un polyol renfermant au moins un groupe carboxyle et (a3) au moins un acide polycarboxylique contenant deux groupes carboxyle ou bien d'un dérivé réactif de cet acide et (a4) au moins un polyol, - au moins 10 moles %, de préférence 30-70 moles %, des constituants employés (a1), (a2), (a3) et (a4) (rapportés à (a1) + (a2) + (a3) + (a4) = 100 moles %) renfermant au moins un élément structural (cyclo)aliphatique contenant au moins 6 atomes de carbone -; ce polyester présente un poids moléculaire moyen (moyenne numérique) inférieur à 2000, de préférence compris entre 500 et 1500, un indice d'acidité compris entre 35 et 240, de préférence entre 50 et 120, un indice OH compris entre 56 et 320, de préférence entre 80 et 200, et tous ses constituants (a1) et (a3) sont condensés par l'intermédiaire d'au moins deux groupes carboxyle. (B) On fait ensuite réagir le polyester ainsi obtenu avec 0,3 à 1,5, de préférence 0,5 à 1,0 équivalent par molécule de polyester d'une résine époxy, présentant un poids équivalent d'époxy compris entre 170 et 1000, de préférence entre 170 et 500, à base d'un biphénol, de préférence du biphénol A, et/ou avec un dérivé de cette résine époxy, contenant au moins un groupe époxy par molécule, dans des conditions de réaction où essentiellement seuls des groupes carboxyle réagissent avec des groupes époxy, pour produire un polyester modifié par une résine époxy, lequel, après neutralisation d'au moins une partie des groupes carboxyle libres, se présente sous une forme diluable dans l'eau.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3636368 | 1986-10-25 | ||
DE19863636368 DE3636368A1 (de) | 1986-10-25 | 1986-10-25 | Wasserverduennbare ueberzugszusammensetzung zur herstellung von hitzehaertbaren ueberzuegen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0327589A1 true EP0327589A1 (fr) | 1989-08-16 |
Family
ID=6312468
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP87907751A Withdrawn EP0327589A1 (fr) | 1986-10-25 | 1987-10-22 | Compositions de revetement diluables dans l'eau pour fabrication de revetements thermodurcissables |
EP87115466A Expired - Lifetime EP0269828B1 (fr) | 1986-10-25 | 1987-10-22 | Compositions de revêtement à l'eau pour la préparation de revêtements thermodurcissables |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP87115466A Expired - Lifetime EP0269828B1 (fr) | 1986-10-25 | 1987-10-22 | Compositions de revêtement à l'eau pour la préparation de revêtements thermodurcissables |
Country Status (10)
Country | Link |
---|---|
EP (2) | EP0327589A1 (fr) |
JP (1) | JPH0621272B2 (fr) |
KR (1) | KR920009300B1 (fr) |
AT (1) | ATE61379T1 (fr) |
AU (1) | AU607732B2 (fr) |
BR (1) | BR8707845A (fr) |
CA (1) | CA1291290C (fr) |
DE (2) | DE3636368A1 (fr) |
ES (1) | ES2020987B3 (fr) |
WO (1) | WO1988003159A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19602555A1 (de) | 1996-01-25 | 1997-08-07 | Basf Lacke & Farben | Wäßrige Bindemittellösungen und -dispersionen |
DE19930555C1 (de) | 1999-07-02 | 2001-01-18 | Basf Coatings Ag | Wäßriger Beschichtungsstoff, insbesondere wäßriger Füller oder Steinschlagschutzgrund |
DE102007054242A1 (de) | 2007-11-14 | 2009-05-20 | Basf Coatings Ag | Verfahren zur Einstellung von definierten Morphologien entmischter Phasen in dünnen Schichten |
DE102007054241A1 (de) | 2007-11-14 | 2009-05-20 | Basf Coatings Ag | Beschichtungsmittel auf Basis unverträglicher Polymerisate und elektrisch geladener Teilchen |
DE102009007633B4 (de) | 2009-02-05 | 2013-09-26 | Basf Coatings Ag | Mehrstufiges Verfahren zur Lackierung metallischer Substrate |
DE102009007632A1 (de) | 2009-02-05 | 2010-08-12 | Basf Coatings Ag | Beschichtungsmittel für korrosionsstabile Lackierungen |
DE102009021071A1 (de) | 2009-05-13 | 2010-11-18 | Basf Coatings Ag | Effektwasserbasislacke mit verbesserten optischen Eigenschaften |
CN104271630B (zh) | 2012-05-31 | 2017-07-28 | 陶氏环球技术有限公司 | 用于水性分散体的环氧树脂 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3749758A (en) * | 1971-09-30 | 1973-07-31 | Ciba Geigy Corp | Polyesters derived from dimethylol propionic acid in admixture with polyepoxides |
GB1509043A (en) * | 1975-04-29 | 1978-04-26 | Ucb Sa | Powdered epoxy resin and polyester coating compositions |
IT1076226B (it) * | 1977-01-17 | 1985-04-27 | Sir Soc Italiana Resine Spa | Composizioni solide reticolabili comprendenti una resina poliestere ed una resina epossidica |
ATE21110T1 (de) * | 1981-10-07 | 1986-08-15 | Hoechst Ag | Verfahren zur herstellung waermehaertbarer, mit wasser verduennbarer lacke und deren verwendung fuer beschichtungen. |
-
1986
- 1986-10-25 DE DE19863636368 patent/DE3636368A1/de not_active Withdrawn
-
1987
- 1987-10-22 EP EP87907751A patent/EP0327589A1/fr not_active Withdrawn
- 1987-10-22 BR BR8707845A patent/BR8707845A/pt not_active IP Right Cessation
- 1987-10-22 KR KR1019880700737A patent/KR920009300B1/ko not_active IP Right Cessation
- 1987-10-22 AT AT87115466T patent/ATE61379T1/de not_active IP Right Cessation
- 1987-10-22 DE DE8787115466T patent/DE3768441D1/de not_active Expired - Lifetime
- 1987-10-22 AU AU83245/87A patent/AU607732B2/en not_active Ceased
- 1987-10-22 ES ES87115466T patent/ES2020987B3/es not_active Expired - Lifetime
- 1987-10-22 WO PCT/EP1987/000624 patent/WO1988003159A1/fr not_active Application Discontinuation
- 1987-10-22 EP EP87115466A patent/EP0269828B1/fr not_active Expired - Lifetime
- 1987-10-22 JP JP63500031A patent/JPH0621272B2/ja not_active Expired - Lifetime
- 1987-10-23 CA CA000550049A patent/CA1291290C/fr not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO8803159A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA1291290C (fr) | 1991-10-22 |
ES2020987B3 (es) | 1991-10-16 |
EP0269828A1 (fr) | 1988-06-08 |
KR880701763A (ko) | 1988-11-05 |
JPH02501312A (ja) | 1990-05-10 |
JPH0621272B2 (ja) | 1994-03-23 |
AU8324587A (en) | 1988-05-25 |
AU607732B2 (en) | 1991-03-14 |
DE3636368A1 (de) | 1988-04-28 |
WO1988003159A1 (fr) | 1988-05-05 |
KR920009300B1 (ko) | 1992-10-15 |
BR8707845A (pt) | 1989-10-03 |
DE3768441D1 (de) | 1991-04-11 |
ATE61379T1 (de) | 1991-03-15 |
EP0269828B1 (fr) | 1991-03-06 |
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