EP0614481A1 - Systemes pour adhesifs thermofusibles reticulables, leur preparation et procede d'assemblage les utilisant - Google Patents

Systemes pour adhesifs thermofusibles reticulables, leur preparation et procede d'assemblage les utilisant

Info

Publication number
EP0614481A1
EP0614481A1 EP92923860A EP92923860A EP0614481A1 EP 0614481 A1 EP0614481 A1 EP 0614481A1 EP 92923860 A EP92923860 A EP 92923860A EP 92923860 A EP92923860 A EP 92923860A EP 0614481 A1 EP0614481 A1 EP 0614481A1
Authority
EP
European Patent Office
Prior art keywords
weight
constituent
parts
objects
composition
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Withdrawn
Application number
EP92923860A
Other languages
German (de)
English (en)
French (fr)
Inventor
Mohamed Moustamsik-Billah
Dominique Chiarabini
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.)
Bostik GmbH
Bostik SA
Bostik Ltd
Bostik AB
Original Assignee
Bostik GmbH
Bostik SA
Bostik Ltd
Bostik AB
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 Bostik GmbH, Bostik SA, Bostik Ltd, Bostik AB filed Critical Bostik GmbH
Publication of EP0614481A1 publication Critical patent/EP0614481A1/fr
Withdrawn legal-status Critical Current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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J131/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Adhesives based on derivatives of such polymers
    • C09J131/02—Homopolymers or copolymers of esters of monocarboxylic acids
    • C09J131/04—Homopolymers or copolymers of vinyl acetate
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/04—Homopolymers or copolymers of ethene
    • C09J123/08—Copolymers of ethene
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives 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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/304—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being heat-activatable, i.e. not tacky at temperatures inferior to 30°C

Definitions

  • the present invention relates to systems for hot-melt adhesives which have the particularity to lead, after application to the surfaces to be assembled, to a crosslinked product which is substantially irreversible making it infusible or difficult to fuse. It also relates to the preparation of these systems, thus that an assembly process using them.
  • the systems for crosslinkable hot-melt adhesives in accordance with the present invention have the double advantage of being able to be implemented very easily in industrial installations, in particular automated installations (robots), such as those of the automobile industry. , and can be applied to many types of objects made from very diverse materials, such as wood, metals, woven or non-woven textiles, glass, porcelain, ceramics, cardboard, paper, stone, concrete and plastics.
  • Patent application EP-A-252,795 discloses a system for hot-melt adhesive comprising: (A) a first composition not containing anhydride groups and comprising: a) at least one polymer chosen from thermoelastic polymers and rubbers synthesis; b) at least one compound containing at least one group capable of reacting with anhydrous groups; c) at least one tackifying resin; d) the.
  • At least one plasticizer if necessary, at least one plasticizer; (B) a second composition comprising: a) at least one polymer chosen from thermoelastic polymers and synthetic rubbers; b) at least one compound containing at least one anhydride group; c) at least one tackifying resin; and d) where appropriate, at least one plasticizer; and
  • a second problem to be solved by the present invention therefore consists in providing a hot-melt adhesive having a breaking stress at least equal to 4 MPa so as to allow the assembly of polyester on polyester or aluminum.
  • the adhesive systems according to the present invention are in particular two-component systems (hereinafter called A and B), one containing in particular epoxy groups and the other including in particular groups susceptible Wheat to react with the latter, once the oxirane cycles are open.
  • a and B two-component systems
  • These components can, each in turn, be melted and kept in fusion for relatively long times compatible with the requirements of an implementation on an industrial scale, cooled and remelted without causing crosslinking.
  • these two components are brought into contact in the molten state (intimate mixing or superposition of a layer of one on a layer of the other), and the expected crosslinking then occurs under the effect of a rise in temperature.
  • the present invention therefore firstly relates to a system for crosslinkable hot-melt adhesive, characterized in that it comprises:
  • A a first composition not containing epoxy groups and comprising: a) at least one polymer chosen from thermoelastic polymers and synthetic rubbers; b) at least one compound containing at least one group capable of reacting with epoxy groups; c) at least one tackifying resin; and d) where appropriate, at least one plasticizer or a wax;
  • (B) a second composition comprising: a) where appropriate at least one polymer chosen from thermoelastic polymers and synthetic rubbers; b) at least one compound containing at least one epoxy group; c) at least one tackifying resin; and d) where appropriate, at least one plasticizer or a wax; and (C) if necessary at least one activator of the reaction between the reactive groups of the constituent (Ab) and the epoxy functions of the constituent (Bb).
  • the molar ratio of the reactive groups of the constituent (Ab) to the epoxy groups constituent (Bb) is at least equal to 1.
  • the latter preferably comprises: from 10 to 60 parts by weight of the constituent (Aa);
  • composition (B) comprises in particular: from 0 to 40 parts by weight of the constituent (Ba); from 20 to 60 parts by weight of the constituent (Bb); from 10 to 60 parts by weight of the constituent (Bc); and - from 0 to 40 parts by weight of the constituent (Bd).
  • thermoelastic polymers falling within the definition of the constituents (Aa) and (Ba) are preferably chosen from the group of copolymers of ethylene and vinyl acetate or of high-strength alkyl acrylate (approximately 20 to 50% by weight) in acetate or acrylate and of high molecular weight (approximately 5,000 to 30,000).
  • Synthetic rubbers falling under the definition of constituents (Aa) and. (Ba) are preferably chosen from copolymers with linear or star blocks, styrene / butadiene, or styrene / isoprene.
  • the compound (Ab) contains at least one amino group.
  • a compound (Ab) there may be mentioned a polyamide with free amino functions.
  • Polyamides which can be used are in particular polyamides obtained from (a) 35 to 49.5% by mole of acid dimeric fat, (b) 0.5 to 15 mol% of monomeric fatty acid with a chain length of 12 to 22 carbon atoms, (c) 2 to 35 mol% of polyetheramine of general formula: H 2 N - R-_ - 0 - (RO) ⁇ - R 2 - NH 2 in which x represents a number between 8 and 80, in particular, between 8 and 40; R and R 2 represent identical or different, aliphatic and / or cycloaliphatic hydrocarbon residues; and R represents an optionally branched aliphatic hydro ⁇ carbon residue having 1 to 6 carbon atoms, and (d) 15 to 48 mol% of aliphatic diamine containing 2 to 40 carbon atoms in the carbon skeleton, the dimer fatty acids possibly be replaced up to 2/3 by aliphatic dicarboxylic acids having 4 to 12 carbon atoms; and polyamides obtained from
  • the compound (Bb) is in particular a polymer containing epoxy groups, and in particular glycidyl groups.
  • epoxidized resins having a functionality, defined as the number of epoxy functions per molecule, at least equal to 2, such as the diglycidyl ether of bisphenol A, butadiene diepoxide, 3,4 3,4-epoxycyclohexylmethyl-epoxycyclohexane carboxylate, vinylcyclohexene dioxide, 4,4'-di (1,2-epoxyethyl) iphenyl ether, 4,4'- (1,2-epoxyethyl) -biphenyl, 2,2-bis (3,4-epoxycyclohexyl) - propane, diglycidyl ether of resorcinol, diglycidyl ether of phloroglucinol, bis (2,3-epoxycyclopentyl)
  • R 3 is a group of formula -CH -0 — R -0-CH - in which R ⁇ is a divalent group chosen from alkylene groups having from 2 to 12 carbon atoms and those comprising at least one aliphatic ring or aromatic substituted or not.
  • triepoxidized or tetraepoxidized resins such as, for example, the triglycidic ether of p-aminophenol, the polyaryl glycidyl ethers, the 1,3,5-tri (1,2-epoxy) enzyme, the 2,2 ',, 4'-tetra-glycidoxybenzophenone, tetraglycidoxytetraphenylethane, 1 * polyglycidyl ether of the novolak phenolformaldehyde resin, triglycidyl ether of glycerol, triglycidyl ether of trimethylolpropane and tetraglycidyl- 4,4'-diaminodipen.
  • the triglycidic ether of p-aminophenol the polyaryl glycidyl ethers
  • the 1,3,5-tri (1,2-epoxy) enzyme the 2,2 ',, 4'-tetra-glycidoxy
  • This polymer (Bb) can also contain, in addition to epoxy groups such as units derived from a monomer glycidyl, units derived from at least one alkene and, where appropriate, units derived from at least one comonomer, chosen in particular from C 1 -C 12 alkyl acrylates and methacrylates.
  • Such copolymers can be obtained either by direct copolymerization of the monomers in accordance with patents FR-A-1,569,004 and FR-A-2,130,279, or by grafting the glycidyl monomer onto an alkene homopolymer or an ethylene copolymer / (meth) acrylate as described in particular by GALUCCI et al. in J. Appl.
  • such a polymer (Bb) contains from 5 to 20% approximately by weight of glycidyl monomer.
  • glycidyl monomers mention may be made of glycidyl acrylate and methacrylate, as well as those of the general formula:
  • - X is chosen from oxygen and sulfur atoms, the NH radical, the NR 7 radicals in which R 7 is an alkyl group having from 1 to 12 carbon atoms, and the oxyalkylene radicals 0- (CH 2 ) n in which n is an integer ranging from 3 to 16 approximately, R 5 is chosen from the hydrogen atom and the alkyl radicals having from 1 to 5 carbon atoms, and R 6 denotes a hydrocarbon chain comprising from 2 to 20 carbon atoms chosen from linear or branched alkyl, cycloalkyl or heteroxyclo- alkyl mono- or polycyclic and alkylaryl alkyl chains, said hydrocarbon chain comprising an oxirane group in the chain, or at the end of the chain in the case of an alkyl or alkylaryl chain , or an oxirane group exo- or endocyclic in the case of a mono- or polycyclic cycloalkyl or heterocycloalkyl chain.
  • the tackifying resins (Ac) and (Bc) are chosen in particular from polyterpenes, optionally functionalized with novolaks, rosins and rosin esters and their hydrogenated derivatives, as well as petroleum resins.
  • the petroleum resins which can be used in the systems according to the invention are resins prepared from hydrocarbon fractions originating from the steam cracking of naphthas, such as aromatic cuts containing at least one alkenylaromatic monomer, aliphatic cuts containing a monomer containing 5 to 6 carbon atoms, such as cyclopentadiene and its derivatives and cyclohexadiene, or even terpene cuts such as turpentine.
  • alkenylaro atic units which can enter into the constitution of these resins, mention may in particular be made of units derived from styrene, alphamethylstyrene, indene, vinyl toluene, methylindenes, betamethylstyrene and paratertiobutylstyrene.
  • terpene units which can enter into the constitution of these resins, mention may in particular be made of units derived from unsaturated cyclic terpenes, preferably monounsaturated, in particular monocyclic, such as 1-p-menthene and tetramethylcyclohexene, and bicyclic monoinsatural such as pinenes, keels, limonene, 4 (10) -thujene, 5-isopropylbicyclo [3.1.0] hex-2-ene, 4-methylenepinane, 2-bornene, 2,2,7-trimen- thyl-2-norbornene and camphene as well as certain bi-unsaturated monocyclic terpenes such as menthadienes.
  • resins which can be used in the context of the present invention are described in documents EP-A-011 393, EP-A-132 291, EP-A-233 074 and FR-A-2 659 972.
  • the plasticizers (Ad) and (Bd) are chosen in particular on the one hand, from semi-aliphatic oils, polyisobutylenes of very low molecular weight, and aromatic, naphthenic or paraffinic petroleum oils, alkylbenzenes, and, d on the other hand, esters derived from acids saturated organics such as phthalates, adipates, sebacates and alkyl azelates.
  • Examples of the latter include diethyl, dibutyl, dicyclohexyl, diethylhexyl, dioctyl, didecyl, butylethylhexyl phthalates, dibutyl, dioctyl, diisooctyl adipates, dibutyl sebacates , dioctyl, diisooctyl, dioctyl and diisooctyl azelates.
  • plasticizers (Ad) and (Bd) of ethylene-vinyl acetate copolymers of very low molecular weight (of the order of 1000-1500), an example of such a copolymer being that containing 28% by weight of vinyl acetate.
  • the waxes (Ad) and (Bd) are chosen in particular from low molecular weight polyethylene waxes (generally less than 5,000) and paraffins.
  • the activator (C) is chosen in particular from tertiary amines, such as dimethylparatoluidine, dimethyllaurylamine, N-bu ' tylmorpholine, N, N-dimethyl-cyclohexylamine, benzyldi ethylamine, pyridine, dimethylamino-4-pyridine , methyl-1-imidazole, tetramethylethylenediamine, tetramethylguanidine, tetramethylhydrazine, N, N-dimethylpiperazine, N, N, N'N'-tetramethyl-1,6-hexanediamine; phosphines, such as triphenylphosphine; aryl- or alkylphosphonium halides, such as ethyltriphenylphosphonium iodide; and tertiary amides of fatty acids, such as tertiary amides of soy fatty acids.
  • compositions (A) and (B) may contain up to 10 parts by weight, per 100 parts by weight of the said composition, of at least one adjuvant such as a wax or paraffin, like polyethylene wax.
  • At least one of the compositions (A) and (B) may contain up to 5 parts by weight, per 100 parts by weight of the said composition, of at least one mineral filler, chosen in particular from silica, alumina, mineral silicates, aluminates and silicoaluminates and talc.
  • at least one mineral filler chosen in particular from silica, alumina, mineral silicates, aluminates and silicoaluminates and talc.
  • At least one of the compositions (A) and (B) may contain up to 1 part by weight, per 100 parts by weight of the said composition, of at least one antioxidant chosen in particular from 2,6-ditertiobutyl - paracresol, bishydroxyanisol, 2,2'-thiodiethyl-bis-3- (3,5-ditertiobutyl-4-hydroxyphenyl) propionate, tetrakis- (methylene 3- (3 ', 5'-ditertiobutyl-4) - hydroxyphenyl) ropionate) ethane, 2,4-bis-N-octylthio-6- (4-hydroxy 3,5-ditertiobutylanilino) 1,3,5-triazine, ditertiobutyl-3,5 hydroxy-4 phenyl- 3 propionate and octadecyl-3,5-ditertio-butyl-4-hydroxyhydrocinnamate.
  • at least one antioxidant chosen in particular
  • the present invention also relates to systems as defined above in which, when it is present, the activator (C) is at least partially incorporated in the composition (A) and / or in the composition ( B).
  • the activator (C) can advantageously be completely incorporated in the composition (A) and / or in the composition (B), so as to form a two-component system as in the case where it is absent.
  • the aforementioned two-component system further comprises a film of thermoplastic material chemically inert with respect to each of the two components and carrying on each of its faces a layer of one of said components.
  • the inert film will consist, for example, of polyethylene or polypropylene or also of an ethylene / alkyl acrylate or ethylene / vinyl acetate copolymer.
  • the present invention also relates to a process for the preparation of a two-component system as defined above. This process is characterized by the fact that the constituents of composition (A) and those of composition (B) are mixed separately at a temperature sufficient to obtain homogeneous liquids, and that each of the two liquid mixtures is cooled. while incorporating the case optionally the activator (C) to at least one of said compositions (A) and (B).
  • each composition (A) and (B) Preferably, mixing the constituents of each composition (A) and (B) at a temperature which is higher by at least 10 ° C above the softening point of said composition, for example between 120 ° C and 170 C.
  • the ⁇ temperature at which one incorporates if necessary 1 * activa ⁇ tor (C) is in particular between 120 ° C and 170 ° C.
  • the process indicated below comprises, after having prepared its two components, the step consisting in applying one of them to one face of said film and the other on the other side.
  • the application of a component to one face of the film can be carried out by coextrusion, or by coating, for example with a roller or by means of a flat die.
  • the present invention also relates to a method of assembling two ' objects, characterized in that one brings to a temperature between 120 ° C and 220 ° C each of the components of the two-component system, as defined above, then: either they are intimately mixed at this temperature, then the resulting hot-melt adhesive is applied to at least one of the two objects to be assembled, and finally one of the two objects to be assembled is applied against 1 ' other, either the two compositions are applied separately, either one after the other on one of the two objects to be assembled, or one on an object to be assembled and the other, on the other object to be assembled , then said objects are applied against each other.
  • the invention also relates to a method for assembling two objects using the system comprising a film of thermoplastic material, this method being characterized by the fact that the two objects are assembled by means of the film, or the assembly is brought to a temperature above the melting point of the thermoplastic film, and sufficient to allow the migration of one of the compounds (Ab) and (Bb) towards the other, their coming into contact causing crosslinking of the system.
  • a method for assembling two objects using the system comprising a film of thermoplastic material, this method being characterized by the fact that the two objects are assembled by means of the film, or the assembly is brought to a temperature above the melting point of the thermoplastic film, and sufficient to allow the migration of one of the compounds (Ab) and (Bb) towards the other, their coming into contact causing crosslinking of the system.
  • a mixture (A) comprising:
  • a mixture (B) comprising:
  • the composition prepared in the first place has a viscosity of 3000 centipoises, that prepared in the second place a viscosity of 15000 centipoises.
  • a first composition (A) is prepared comprising: - 5.5 parts by weight of VERSAMIDE 140,
  • This composition (A) has a viscosity at 175 ° C of 3900 centipoise.
  • the following properties are determined for the two-component system obtained by equiponderal mixing of the composition (A) described above and of the composition (B) of Example 1 - softening temperature (according to NFT 76106): 113 ° C after 4 days. breaking stress (according to NFT 76 107): 1.4 MPa peeling force (according to NFT 76 112): 4.4 N.
  • a first composition (A) comprising:
  • composition (A) has a viscosity at 175 ⁇ C of 30,800 centipoise.
  • composition (B) is prepared comprising:
  • n 2 or 3
  • This composition (B) has a viscosity at 175 ° C of 1250 centipoise.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
EP92923860A 1991-11-29 1992-10-26 Systemes pour adhesifs thermofusibles reticulables, leur preparation et procede d'assemblage les utilisant Withdrawn EP0614481A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9114770A FR2684387A1 (fr) 1991-11-29 1991-11-29 Systemes pour adhesifs thermofusibles reticulables, leur preparation et procede d'assemblage les utilisant.
FR9114770 1991-11-29
PCT/FR1992/001001 WO1993011200A1 (fr) 1991-11-29 1992-10-26 Systemes pour adhesifs thermofusibles reticulables, leur preparation et procede d'assemblage les utilisant

Publications (1)

Publication Number Publication Date
EP0614481A1 true EP0614481A1 (fr) 1994-09-14

Family

ID=9419481

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92923860A Withdrawn EP0614481A1 (fr) 1991-11-29 1992-10-26 Systemes pour adhesifs thermofusibles reticulables, leur preparation et procede d'assemblage les utilisant

Country Status (6)

Country Link
EP (1) EP0614481A1 (enrdf_load_stackoverflow)
AU (1) AU2948692A (enrdf_load_stackoverflow)
FR (1) FR2684387A1 (enrdf_load_stackoverflow)
PT (1) PT101097A (enrdf_load_stackoverflow)
WO (1) WO1993011200A1 (enrdf_load_stackoverflow)
ZA (1) ZA929281B (enrdf_load_stackoverflow)

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BR9510644A (pt) * 1995-09-20 1999-01-05 Minnesota Mining & Mfg Composiç o curável e processo
CN1074780C (zh) * 1995-09-20 2001-11-14 美国3M公司 环氧树脂和聚烯烃树脂的半互穿聚合物网络及其制造方法和应用
US6077601A (en) 1998-05-01 2000-06-20 3M Innovative Properties Company Coated abrasive article
US6136398A (en) * 1998-05-01 2000-10-24 3M Innovative Properties Company Energy cured sealant composition
US6057382A (en) * 1998-05-01 2000-05-02 3M Innovative Properties Company Epoxy/thermoplastic photocurable adhesive composition
US6228133B1 (en) 1998-05-01 2001-05-08 3M Innovative Properties Company Abrasive articles having abrasive layer bond system derived from solid, dry-coated binder precursor particles having a fusible, radiation curable component
US6274643B1 (en) 1998-05-01 2001-08-14 3M Innovative Properties Company Epoxy/thermoplastic photocurable adhesive composition
ATE455134T1 (de) * 2004-07-08 2010-01-15 Arkema France Polymermaterial mit ketten mit imidazolidonfunktionen
FR2924715B1 (fr) * 2007-12-06 2012-10-12 Arkema France Materiau forme de molecules arborescentes comportant des groupes associatifs
DE102012009055B4 (de) 2012-05-08 2015-06-03 Carl Freudenberg Kg Thermisch fixierbares Flächengebilde, Verfahren zu seiner Herstellung und seine Verwendung als Einlagestoff zur Fixierung an einem Oberstoff

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FR2600663B1 (fr) * 1986-06-27 1988-08-05 Charbonnages Ste Chimique Compositions pour adhesifs thermofusibles reticulables, les adhesifs correspondants ainsi que leurs procedes de preparation et d'application
EP0289632A1 (en) * 1987-05-04 1988-11-09 American Cyanamid Company High green strength induction curable adhesives
US4962138A (en) * 1988-05-27 1990-10-09 W. R. Grace & Co.-Conn. Reactive hot melt structural adhesive
EP0442700B1 (en) * 1990-02-14 1996-01-03 Union Camp Corporation Two-component curable hot-melt resin compositions

Non-Patent Citations (1)

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Title
See references of WO9311200A1 *

Also Published As

Publication number Publication date
AU2948692A (en) 1993-06-28
WO1993011200A1 (fr) 1993-06-10
PT101097A (pt) 1994-02-28
FR2684387B1 (enrdf_load_stackoverflow) 1994-08-19
FR2684387A1 (fr) 1993-06-04
ZA929281B (en) 1993-06-02

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