EP0612343A1 - Revetements pour scellage a chaud a base de dispersions - Google Patents

Revetements pour scellage a chaud a base de dispersions

Info

Publication number
EP0612343A1
EP0612343A1 EP92923312A EP92923312A EP0612343A1 EP 0612343 A1 EP0612343 A1 EP 0612343A1 EP 92923312 A EP92923312 A EP 92923312A EP 92923312 A EP92923312 A EP 92923312A EP 0612343 A1 EP0612343 A1 EP 0612343A1
Authority
EP
European Patent Office
Prior art keywords
systems according
reactive systems
component
reactive
component reactive
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
EP92923312A
Other languages
German (de)
English (en)
Inventor
Gerd Bolte
Günter Henke
Ulrike Brüninghaus
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0612343A1 publication Critical patent/EP0612343A1/fr
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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of 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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • 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
    • C08G2270/00—Compositions for creating interpenetrating networks
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions

Definitions

  • the invention relates to two-component, film-forming reactive systems for the planar connection and / or coating of substrates, in particular for heat seal coatings, based on aqueous dispersions
  • the invention relates to a method for producing composites and adhesive-coated substrates.
  • Solvent-based adhesive systems based on modified polyurethane, polyester, acrylate and epoxy resins are known to the person skilled in the art for such purposes. In addition to the basic problem of solvents, such systems often have the disadvantage that the curing times are much too long, for example up to 14 days for polyurethane adhesive systems, or the curing temperatures are too high, for example up to 240 ° C for epoxy resin or acrylate systems.
  • JP 87/153371 and JP 85/118781 have disclosed adhesives for flexible, water-based printed circuits which contain dispersions of acrylate (co) polymers and epoxy compounds.
  • a major disadvantage of such systems are the relatively long curing times, for example 15 hours at 130 ° C. in JP 87/153371.
  • aqueous polyurethane adhesives are known in Ba ⁇ sis Polyuretha ⁇ dispersionen (A) obtained from Polytetramethyle ⁇ glykol (MW 400 to 2000) r an organic diisocyanate and a Dimethylolcarbonklare and hydrazine or dihydrazides as Ketten ⁇ extending agents neutralized with tertiary amines of and a water-soluble Compound (B) with 2 or more epoxy or aziridial rings per molecule.
  • this adhesive for example PET and polypropylene
  • the person skilled in the art finds no indication that such adhesives could be suitable for heat seal coatings.
  • water-based reactive systems are to be made available which are capable of achieving high adhesive strengths even with difficult-to-connect substrates such as polyimides.
  • the curing time should be relatively short and the curing temperature should be below 200 ° C.
  • the special requirement of blocking resistance should be able to be met. This is to be understood as the non-stickiness of a film at normal room and storage temperatures, which was produced by coating a substrate with the reactive system according to the invention and then drying.
  • a new raw material base or a different polymer class is to be developed as a starting material for such systems.
  • the object was achieved according to the invention by two-component, film-forming reactive systems for the surface bonding and / or coating of substrates, in particular for heat seal coatings, based on aqueous dispersions of at least one resin (I) curable with epoxides and of epoxy compounds as hardeners (II), characterized in that that the curable resin (Ia) contains polyurethane polymers with functional groups reactive towards epoxides and, if desired, further resins.
  • the two-component reactive system according to the invention thus receives dispersions of an epoxy-curable resin (I) and dispersed epoxy compounds as hardener (II).
  • the curable resin (Ia) contained in (I) consists of polyurethane polymers with functional groups reactive towards epoxides. Amino, carboxyl and / or hydroxyl groups are particularly suitable as reactive functional groups. Carboxyl groups are preferred. Such modified polyurethane polymers are known to the person skilled in the art.
  • polyurethanes There are basically a number of basic materials that are suitable for the production of polyurethanes. These can be roughly divided into the so-called polyol component and the so-called Divide the isocyanate component.
  • polyester polyols, polyether polyols and polyester polyether polyols are of particular importance.
  • polyurethanes based on polyester polyols are preferred. These are generally obtained by reacting polyfunctional alcohols with polyfunctional carboxylic acids.
  • Suitable isocyanates for the production of polyurethanes are, for example, aliphatic, aromatic and / or alicyclic polyfunctional isocyanates.
  • MDI 4,4'-diphenylmethane diisocyanate
  • IPDI isophorone diisocyanate
  • TDI tolylene diisocyanate
  • TXDI tetramethylxylene diisocyanate
  • chain extenders which are physiologically questionable such as hydrazine, diaminodiphenylmethane or the isomers of phenyldiamine and the carbohydrazides or hydrazides of dicarboxylic acids.
  • polyurethanes containing hydroxyl groups can be obtained by choosing a ratio of OH to NCO groups which is greater than 1 when the polyol and isocyanate components are reacted.
  • Carboxyl groups can be inserted, for example, by adding a portion of D hydroxycarboxylic acids to the polyol component before reaction with the isocyanate component.
  • Suitable polyurethanes containing amino groups can be prepared, for example, by reacting polyurethanes containing isocyanate groups with polyfunctional amino compounds if the isocyanate groups are in short supply * . Further information on the introduction Such functional groups, in particular the carboxyl groups which are particularly preferred in the sense of the invention, can also be found in the published European application already mentioned.
  • the suitable polyurethane polymers can also contain different groups which are reactive towards epoxides. However, those are particularly suitable in which the sum of acid number, OH number and amine number is 0.1 to 40 on average. Polyurethane polymers in which the sum mentioned is in the range from 0.3 to 20 are particularly suitable. A range from 0.5 to 5 is preferred. In principle, those polyurethanes are preferred according to the invention which each contain at least on average two functional groups which are reactive toward epoxides. In the case of polymers of this type, those in which these reactive groups are arranged at the ends are particularly suitable. With regard to the application properties, in particular the flexibility and adhesive strength, polyurethanes are preferably used which have an average molecular weight of about 7,000 to 50,000. Particularly good results are achieved with polyurethanes with an average molecular weight in the range from 10,000 to 30,000. In this context and in the following, the mean molecular weight means the weight average.
  • Suitable epoxy compounds are known to the person skilled in the art from the patent literature and also from encyclopedias. For example, in Ullmann, Encyclopedia of Industrial Chemistry, 4th Edition, Volume 10, Verlag Chemie, Weinheim / Bergstrasse 1974, p. 563 ff., The manufacture of epoxides, their properties and their use are described in detail. The technically most important epoxy compounds include those based on bisphenol A and / or novolak. In addition to these, heterocyclic epoxides are also particularly suitable. Epoxy resin dispersions are used according to the invention. In principle, everyone is dispersible epoxy resins suitable. This applies both to emulsifier-containing dispersions and to corresponding self-emulsifying systems.
  • Epoxy compounds such as triglycidyl isocyanorate, polyethylene glycol diglycidyl ether or sorbitol polyglycidyl ether are also suitable. Instead of the dispersible epoxy resins, water-soluble epoxy compounds can also be used in whole or in part.
  • the epoxides suitable according to the invention preferably contain on average at least two epoxy groups. Epoxy compounds with an epoxy equivalent in the range from 100 to 4,000 are particularly preferred. An epoxide equivalent is understood to mean the amount in grams that one mole of epoxide contains. Particularly good results are obtained with epoxy compounds where this value is between 150 and 600.
  • the dispersion of a resin (I) curable with epoxides contains, in addition to the polyurethanes (Ia) already described in more detail, as further curable resin (Ib) acrylic and / or methacrylate homo- or copolymers with carboxyl and / or methylol groups in dispersed form.
  • Modified (meth) acrylate polymers of this type are known to the person skilled in the art. Examples of suitable (meth) acrylates for the production of such polymers are acrylic acid and methacrylic acid and their salts and esters. The alcohol component of these esters preferably contains 1 to 6 carbon atoms.
  • the person skilled in the art can expediently fall back on those which have been prepared by emulsion polymerization.
  • the monomers mentioned can also be (co) polymerized with other ethyl ' unsaturated monomers insofar as they are copolymerizable. Suitable monomers of this type are all those which contain ethylenically unsaturated or vinyl groups.
  • the vinyl compounds include, for example, vinyl chloride and the vinyl esters such as vinyl acetate, vinyl propionate but also vinyl fatty acid esters such as vinyl laurate and furthermore vinyl alcohol.
  • Suitable styrene compounds are styrene, halostyrenes such as chlorostyrene, fluorostyrene and iodostyrene, alkylstyrenes such as methylstyrene and 2,4-diethylstyrene, cyanostyrenes, hydroxystyrenes, nitrostyrenes, aminostyrenes and / or phenylstyrenes.
  • Suitable derivatives of the acrylic compounds include, for example, acrylonitrile.
  • the carboxyl groups present according to the invention in the above-described polymers can be inserted, for example, by using acrylic acid and / or methacrylic acid as monomers in the polymerization. Methylol groups are obtained, for example, by using hydroxystyrenes or by polymerizing vinyl acetate and subsequent saponification.
  • Suitable monomers include e.g. Vinyl compounds, the acrylates already mentioned and corresponding derivatives.
  • Suitable polymers for the purposes of the invention are, for example, (meth) acrylic-styrene-acrylonitrile copolymers or polybutyl ethacrylate.
  • the homopolymers of acrylic acid and methacrylic acid are also suitable.
  • Polymers described above are particularly preferred if they have an average molecular weight of 50,000 to 300,000.
  • preference is given to homo- or copolymers whose sum of acid number and OH number is in the range from 1 to 40. The have particularly good results mentioned polymers if this sum is between 3 and 15, but in particular in the range from 4 to 10.
  • the ratio of the curable resins is of particular importance with regard to the application-technical results.
  • the weight ratio of the curable resins (la) to (Ib) in the sense of the invention can preferably be in the range from 100: 0 to 5: 95. Roughly speaking, the rule applies here that the film formed from the reactive system becomes more flexible with an increased proportion of polyurethane, while the temperature stability is favored by increasing the proportion of the other curable resin. Even a relatively small proportion of (Ib) leads to significantly improved values with regard to the latter property.
  • a preferred range is therefore between 99: 1 to 25:75.
  • a particularly optimal and therefore preferred range from (la) to (Ib) is between 98: 2 to 50:50.
  • the stated ratios relate to the solids content of the Di ⁇ version.
  • the ratio of curable resin (I) to hardener (II) is also of particular importance.
  • the relationships of the individual components to one another and the specification of these components interact with one another and influence the application-technical properties of the reactive systems according to the invention or the films formed therefrom.
  • the ratio of the amounts of the individual components and the molecular weights and functionalities of the components enables reactive systems to be formulated within a wide range of application properties. Formulations with a high initial stickiness as well as those that result in a particularly non-blocking coating can be composed.
  • the weight ratio of resin (I) to hardener (II) can therefore vary in a preferred range from 1: 5 to 10: 1.
  • the dispersion in a preferred embodiment of the invention in addition to the two components (I) and (II ) also contain either 2 15% by weight, based on the solids content, of a polyaziridi or 2 to 30% by weight, based on the solids content, of a phenol resole resin.
  • the polyaziridine is a polyfunctional aziridine with the general formula
  • R is an organic aliphatic radical or an H
  • X is an alkylene group which may contain an ester, ether, amide or similar inert group
  • R ' is an alkyl group with 1 to 10 carbon atoms and m is a number from 2 to 4.
  • X can be prepared by reacting alkyl aziridines with compounds containing NH-reactive groups.
  • the phenol resole resin is also a known product. They are obtained by the condensation of phenols, creoles, etc. with formaldehyde. Liquid phenol resoles are preferred. Their addition brings about a further improvement in the temperature resistance of the adhesive film.
  • the reactive systems can contain not only the dispersions of resin (I) and hardener (II) but also conventional additives up to a total amount of 30% by weight, based on the total solids content of the reactive system.
  • Catalysts such as, for example, tertiary amines or phosphoric acid or their derivatives may be present, preferably up to 1% by weight.
  • Adhesion promoters such as silanes, titanates and zirconates can have a proportion of up to 1% by weight.
  • high-boiling solvents up to 5% by weight can be added.
  • Defoamers and wetting aids are usually up to 2% by weight.
  • Acid anhydrides or styrene-maleic anhydride resins can contain up to 10% by weight as crosslinking agent or wetting aid.
  • a flexibilizer for example NBR rubber with a molecular weight of 30,000 and 200,000, can be added up to 10% by weight.
  • Polyesters with an average molecular weight of about 600 to 15,000 or else GlykoTether up to 5% by weight can be present as plasticizers.
  • Other possible additives, such as protective agents, preservatives, etc., and their effective amounts are known to the person skilled in the art from the literature and are not listed further here.
  • the weight percentages given above also relate to the total solids content of the reactive system. This is preferably in Range from 30% by weight to 75% by weight, in particular in the range from 40% by weight to 65% by weight.
  • the reactive systems according to the invention can be used to produce adhesive-coated substrates such as are suitable, for example, for producing flexible printed circuits.
  • the procedure is such that the reactive system is applied to the substrate, for example a metal foil such as copper foil, after the dispersions of resins (I) and hardener (II) have been mixed intimately. This can be done by rolling, spraying, brushing, knife coating or dipping.
  • the layer thickness of the applied reactive system is generally 15 to 40 ⁇ m. A layer thickness of 20 to 25 ⁇ m is preferred.
  • the substrate coated in this way is then dried at a temperature which is below the reaction temperature. The drying temperature should therefore not or not significantly exceed 120 ° C. Drying can take place, for example, in customary drying channels.
  • Air per hour in the coating of films according to the invention can be worked at film speeds of 10 to 20 meters per minute.
  • An adhesive-coated substrate is thus obtained which is block-resistant, ie is not tacky at normal storage and room temperatures.
  • Such block-resistant systems have the advantage that the substrate on the coated side does not have to be covered by an additional protective film for storage.
  • Films coated according to the invention can thus be stored in the form of rolls without protective layers or cover films.
  • the re-use of these coated substrates according to the invention thus also eliminates the step of removing the protective or '. Cover film.
  • Such substrates coated in accordance with the invention can be produced in a process for the production of Laminates or composites are processed further. For this purpose, they are hot pressed with another substrate. This is understood to mean that the adhesive-coated substrate is reactivated by heat and is connected to the other substrate by pressure, and the curing then takes place.
  • the pressing pressure during the hot pressing process is usually in the range from 5 to 200 bar.
  • the setting of the optimum pressure for the respective combination lies within the experience of the person skilled in the art.
  • Reactivation and curing preferably take place at temperatures between 140 ° C to 170 ° C.
  • Another advantage of the invention lies in the short curing times, which can be in the range from 30 to 60 minutes.
  • the reactive systems of the invention can also be used for the in-line production of laminates or composites.
  • laminates or composites can also be produced with more than two substrates, these being able to be made from a wide variety of materials.
  • the person skilled in the art can select the ratio of the resins (Ia) and (Ib) to one another and to the hardener component, as already described, in such a way that the reactive system according to the invention has a somewhat higher initial maturity. This is often at the expense of the block resistance, which, however, plays no role in the in-1ine experienced.
  • the reactive systems according to the invention are therefore particularly suitable for the production of multilayer composites or laminates.
  • the substrates can be metal foils, plastic foils, fabrics, nonwovens, special papers and / or cardboard. For example, copper, aluminum, lead and constant anfo be listed as metal foils.
  • PETP polyethylene terephthalate
  • PI polyimide
  • PC polycarbonate
  • PEEK polyester ether ketone
  • LCP liquid crista polymers
  • fabrics made of PETP or polyamide (PA) are very suitable.
  • Nonwovens made of PETP or polyaramide can be used.
  • those based on polyaramid or pressboard are also suitable.
  • Copper foils coated according to the invention result under the influence of heat and pressure in the manner described with other flexible substrates such as Kapton R or polyester foil composites which are suitable for the manufacture of flexible, printed circuits.
  • This type of further processing of heat-seal-coated foils is called dry lamination.
  • the reactive systems according to the invention result in films which have high mechanical, thermal and chemical stability in the laminates or composites mentioned.
  • the reactive systems according to the invention can also be used for the production of high-temperature-resistant insulating materials.
  • Insulating materials are understood here in particular to mean cable windings, cover foils for circuits and windings for coils.
  • Aqueous-based reactive system according to the invention contains in dispersed form
  • Aqueous-based reactive system according to the invention contains in dispersed form
  • this reactive system After drying, this reactive system produces a coating with high initial tack and is particularly suitable for in-line lamination.
  • a reactive system according to Example 1 with a thickness of 20-25 ⁇ m was applied to a copper foil of 35 ⁇ m. After drying at 120 ° C., a 20 ⁇ m thick, closed, non-blocking adhesive was obtained.
  • the coated copper foil according to Example 3 was laminated against a 23 ⁇ m thick polyethylene terephthalate foil at 140 ° C.
  • the material cracked during the bond adhesion test.
  • the coated copper foil according to Example 3 was laminated against a 50 ⁇ m thick Kapton R foil at 170 ° C. In the test for composite adhesion, material cracked. In the test for temperature stability, no delamination or bubble formation was found after one day at 220 ° C. After tempering at 170 ° C for half an hour, a solder bath resistance was found at 288 ° C for 60 seconds.
  • a polyester film was coated with a reactive system according to Example 1, dried and then with a polyamide film laminated at 140 ° C.
  • the bond adhesion test showed material tear. When tested for temperature resistance, there was no delamination or blistering after 1 day at 155 ° C.
  • a polyester film was coated with a reactive system according to Example 1 and, after drying, hot-pressed with a press chip substrate. Material tear was also obtained here in the test for bond adhesion. In the test for temperature stability, there was no detachment of the substrates or blistering after one day at 130 ° C.
  • the following example shows the positive effect of polyaziridine: A polyester film was coated with a reactive system according to Example 2, to which 5% of the polyazaridine CROSSLINKER CX-100 (from ICI), based on the solids content, were added, dried and dried at approx 60 ° C laminated in-line against polyaramid paper. The bond adhesion test resulted in material demolition. After 48 hours at 155 ° C., the test for temperature resistance showed neither delamination nor blistering.
  • the following example shows the positive effect of a phenol-resole resin: a) 2 parts by weight of the polyurethane described in Example 1, 10 parts by weight of the acrylic ester copolymer described in Example 1, 6 parts by weight of the epoxy resin described in Example 1 were mixed, applied to a Cu foil and dried at 120 ° C., b) 1 part by weight of a liquid phenolic resole resin was added to the above mixture and the mixture was also applied to a Cu foil and dried at 120 ° C.
  • Both coatings were pressed with 8 layers of a phenolic prepreg at 170 ° C for 1 h.
  • the bond strength of sample a) was 4.2 to 4.5 N / 3 mm, that of sample b) 4.6 to 4.9 N / 3 mm.
  • the solder bath resistance of sample a) was 2 s, that of sample b) 22 s at 260 ° C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
  • Sealing Material Composition (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Epoxy Resins (AREA)
  • Thermotherapy And Cooling Therapy Devices (AREA)

Abstract

Il est décrit des systèmes réactionnels destinés à des connexions planes et/ou à des revêtements plans de substrats, notamment à des revêtements pour scellage à chaud, à base de dispersions aqueuses d'une résine durcissable aux époxydes (I) et de composés époxy comme durcisseurs (II). En utilisant comme résine durcissable (Ia) des polymères de polyuréthanne à groupes fonctionnels réagissant vis-à-vis des époxydes, on peut fabriquer des substrats cohérents revêtus par scellage à chaud qui peuvent être utilisés, par exemple, pour la fabrication de circuits imprimés souples.
EP92923312A 1991-11-15 1992-11-06 Revetements pour scellage a chaud a base de dispersions Pending EP0612343A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4137512 1991-11-15
DE4137512A DE4137512A1 (de) 1991-11-15 1991-11-15 Heisssiegelbeschichtung auf dispersionsbasis
PCT/EP1992/002553 WO1993010202A1 (fr) 1991-11-15 1992-11-06 Revetements pour scellage a chaud a base de dispersions

Publications (1)

Publication Number Publication Date
EP0612343A1 true EP0612343A1 (fr) 1994-08-31

Family

ID=6444832

Family Applications (2)

Application Number Title Priority Date Filing Date
EP92119076A Expired - Lifetime EP0542160B1 (fr) 1991-11-15 1992-11-06 Revêtement thermoscellable à base de dispersion
EP92923312A Pending EP0612343A1 (fr) 1991-11-15 1992-11-06 Revetements pour scellage a chaud a base de dispersions

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP92119076A Expired - Lifetime EP0542160B1 (fr) 1991-11-15 1992-11-06 Revêtement thermoscellable à base de dispersion

Country Status (12)

Country Link
US (1) US5464494A (fr)
EP (2) EP0542160B1 (fr)
JP (1) JP3794432B2 (fr)
AT (1) ATE132176T1 (fr)
BR (1) BR9206758A (fr)
CA (1) CA2123610C (fr)
DE (2) DE4137512A1 (fr)
DK (1) DK0542160T3 (fr)
ES (1) ES2082331T3 (fr)
GR (1) GR3019021T3 (fr)
NO (1) NO308864B1 (fr)
WO (1) WO1993010202A1 (fr)

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JP5265854B2 (ja) * 2005-12-08 2013-08-14 昭和電工株式会社 熱硬化性樹脂組成物、熱可塑性樹脂溶液および皮膜形成材料ならびにこれらの硬化物
ES2350332B1 (es) * 2009-05-05 2011-11-15 Vipeq Hispania 2008 S.L Formulacion con propiedades aislantes
US8742010B2 (en) 2010-04-09 2014-06-03 Bayer Materialscience Llc Two-component waterborne polyurethane coatings
JP5663780B2 (ja) * 2011-03-08 2015-02-04 和歌山県 アクリレート系共重合体、およびそれを含む樹脂組成物、ならびにそれをコーティングした受容層付き基板
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KR102445064B1 (ko) 2015-09-03 2022-09-19 에이비 엘렉트로룩스 로봇 청소 장치의 시스템
KR20220025250A (ko) 2017-06-02 2022-03-03 에이비 엘렉트로룩스 로봇 청소 장치 전방의 표면의 레벨차를 검출하는 방법
CN111093447B (zh) 2017-09-26 2022-09-02 伊莱克斯公司 机器人清洁设备的移动控制

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JP3794432B2 (ja) 2006-07-05
DE59204837D1 (de) 1996-02-08
DK0542160T3 (da) 1996-05-20
JPH07501095A (ja) 1995-02-02
GR3019021T3 (en) 1996-05-31
ATE132176T1 (de) 1996-01-15
NO308864B1 (no) 2000-11-06
WO1993010202A1 (fr) 1993-05-27
EP0542160A1 (fr) 1993-05-19
NO940735D0 (no) 1994-03-03
CA2123610C (fr) 2002-07-02
CA2123610A1 (fr) 1993-05-27
BR9206758A (pt) 1995-10-31
ES2082331T3 (es) 1996-03-16
EP0542160B1 (fr) 1995-12-27
DE4137512A1 (de) 1993-05-19
US5464494A (en) 1995-11-07
NO940735L (no) 1994-03-03

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