EP1161507A1 - Adhesifs solubles - Google Patents

Adhesifs solubles

Info

Publication number
EP1161507A1
EP1161507A1 EP00909120A EP00909120A EP1161507A1 EP 1161507 A1 EP1161507 A1 EP 1161507A1 EP 00909120 A EP00909120 A EP 00909120A EP 00909120 A EP00909120 A EP 00909120A EP 1161507 A1 EP1161507 A1 EP 1161507A1
Authority
EP
European Patent Office
Prior art keywords
adhesive
mercapto
cleavage
bonds
acid
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Withdrawn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
EP00909120A
Other languages
German (de)
English (en)
Inventor
Christian Kirsten
Andreas Ferencz
Michael Hirthammer
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 EP1161507A1 publication Critical patent/EP1161507A1/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Withdrawn legal-status Critical Current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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C08K5/47—Thiazoles
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/04—Polysulfides
    • 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
    • C09J2463/00—Presence of epoxy resin
    • 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
    • C09J2481/00—Presence of sulfur containing polymers

Definitions

  • the present invention relates to adhesive compositions based on binders which contain di- or polysulfide bonds and are suitable for producing releasable adhesive bonds.
  • the present invention further relates to cleavage reagents for detaching adhesive bonds and a method for producing and detaching adhesive bonds.
  • EP-A-735121 describes an adhesive film section for a residue-free and damage-free and releasable adhesive bond consisting of a double-sided adhesive film with a handle protruding from the adhesive film, to which pulling in the direction of the Bonding level the bond is detachable.
  • this method can only be used if the adhesive layer of the adhesive film is a pressure sensitive adhesive. With such adhesive connections, however, only slight tension or Achieve peel strengths, so that this method can only be used for fixing small objects such as hooks and the like in the household area.
  • DE-A-4230116 describes a rubber composition containing a blend of an aliphatic polyol with an aromatic dianhydride.
  • This adhesive composition enables the bond to be dissolved in aqueous alkaline systems, specifically called soda solutions or alkali solutions. It is proposed to use these aqueous alkaline-soluble adhesives for the rational production of magnetic parts and other small parts, the adhesive only being used for the production of auxiliary pushings in material processing.
  • Very similar adhesives are also known as labeling adhesives, which allow the labels to be peeled off in an aqueous or aqueous alkaline environment in beverage bottles and similar containers.
  • DE-A-4328108 describes an adhesive for floor coverings and a method for detaching these bonded floor coverings with the aid of microwave energy.
  • the adhesive should be electrically conductive and softenable by a microwave device.
  • Solvent-free contact adhesives based on (aqueous) polymer dispersions containing copper powder or aluminum powder are specifically proposed.
  • the glued pieces of floor covering are to be placed in a microwave device to release the adhesive connection, so that the adhesive layer can be softened, so that the pieces of floor covering can be removed manually after the adhesive layer has softened.
  • WO 94/12582 describes a pressure sensitive adhesive based on a mixture of an aqueous polymer dispersion and an adhesive dissolved in an organic solvent, as well as tackifiers and production agents. This pressure sensitive adhesive has a constant adhesive force over a wide temperature range and enables mechanical separation of the adhesive bonds. It is stated that these adhesive connections are suitable for bonding insulation and / or decorative surface parts such as insulation materials or plastic films.
  • EP-A-521825 describes a releasable adhesive connection in which the parts connected to one another are joined by means of an adhesive bead inserted between them.
  • This bead of adhesive contains a flat thermoplastic separating element. When the adhesive connection is heated by current or radiation supply, this thermoplastic separating layer is softened, so that the parts connected to one another can be mechanically separated from one another.
  • EP-A-521825 suggests using such releasable adhesive bonds in direct glazing in vehicle construction.
  • DE-A-19526351 describes a solvent gel for lacquers, paints and adhesives based on organic solvents with the addition of network thickeners and other conventional agents.
  • the use as a stripping agent in the stripping of 2-component lacquers is mentioned as a concrete field of application. Although it is mentioned that such mixtures are also suitable for use with 2-component adhesives, there is no concrete information on how to loosen such adhesive connections.
  • WO 87/01724 describes a composition for removing cured polysulfide sealants or coatings.
  • Solvent or solvent mixture consisting of dimethylformamide or dimethylacetamide or their mixture with aromatic solvents such as toluene or xylene, an alkali metal or ammonium thiolate based on alkyl or phenyl thiolates and applied to hardened polysulfide sealants or coating materials, in order to then remove them from their substrates, such as e.g. B.
  • aromatic solvents such as toluene or xylene
  • an alkali metal or ammonium thiolate based on alkyl or phenyl thiolates and applied to hardened polysulfide sealants or coating materials, in order to then remove them from their substrates, such as e.g. B.
  • WO 97/00283 describes a method for reprocessing cured or partially cured polysulfide and / or polymer captan compositions.
  • hardened polysulfide materials are depolymerized in a solution of a depolymerization agent based on vulcanization accelerators in a non-volatile liquid, in order to be subsequently reused as a component of a hardener component of 2-component polysulfide and / or polymercaptan adhesives / sealants or coating materials become.
  • Evidence of a loosening of adhesive bonds by this method is not disclosed.
  • detachable adhesive connections described in the abovementioned prior art are each to be used only in a very narrowly limited field of application, in particular there are no adhesive compositions which combine the easy and quick detachability or easy removal of the adhesive connection with high strength of the bond and stability against external influences .
  • the as yet unpublished PCT / EP 98/04667 describes adhesives in which at least one structural component contains di- or polysulfide bonds and which can be dissolved again after curing by applying solutions of cleavage agents based on mercapto compounds. This makes it possible to chemically separate bonded components in the adhesive joint.
  • the cleavage agent can also be admixed in a form of the adhesive formulation which is inert at room temperature, it being possible for the cleavage to take place at an elevated temperature after activation of the reagent. No specific formations of this inert form of the splitting agent are mentioned.
  • solvent-containing cleavage agents makes it possible to detach adhesive bonds again, it is desirable to be able to do without solvent-based cleavage agents since this procedure
  • inert at room temperature or use temperature with respect to the cleavage agent means that this cleavage agent is dispersed in the adhesive matrix at room temperature or the use temperature of the bonded unit, but cannot cause cleavage of the di- or polysulfide bonds of the adhesive matrix in this temperature range Rather, this cleavage and thus loosening of the adhesive connection should only take place after a triggering step, ie after the activation of the cleavage reagent.
  • Another object of the present invention is a method for producing and releasing adhesive bonds with the following essential process steps:
  • this adhesive composition can be a one-component system that the user can apply directly without mixing components.
  • the adhesive system can also consist of 2 or more components to be stored separately, which are only mixed with one another immediately before application.
  • Curing of the adhesive at room temperature i.e. by reaction of the individual components with one another in the case of multi-component systems or by reaction of the single-component system with atmospheric moisture and / or atmospheric oxygen.
  • Other options for curing are the supply of heat, UV light or electron beams. The curing process depends on the crosslinking mechanism of the components.
  • this separation process can be further accelerated by heating the bonded component or the bond point.
  • the separation of the bonded components can be further accelerated by mechanical stress on the adhesive joint.
  • Substantial constituents of the structural components of the binder according to the invention are therefore compounds which have at least one disulfide or polysulfide bond of the general formula
  • XR 1 -S x -R 2 -Y (I) contain.
  • R 1 and R 2 are divalent alkyl and / or aryl residues, in the simplest case a C 2 to C 8 alkylene group or a divalent aromatic residue such as 1,2-, 1,3- or 1,4-phenylene , Diphenylene, naphthylene or similar aromatic radicals.
  • X and Y can independently of one another denote any functional group capable of reaction, preference being given to primary or secondary amino groups, hydroxyl groups, carboxyl groups.
  • X and / or Y can be mercapto groups, epoxy groups, isocyanate groups, alkoxysilyl groups or also olefinic double bonds, in the latter case R 1 and / or R 2 can be replaced by a covalent bond, x is an integer in the range between 2 and 8, 2 is particularly preferred.
  • Examples of structural components according to formula I which contain olefinic double bonds can be prepared in the following way:
  • dithiodial alcohols or dithiodiamines are reacted with diisocyanates in such a way that isocyanate-terminated disulfide compounds result, ie the diisocyanate component is converted into a stoichiometric one Excess over the dithiodial alcohol or dithiodiamine component used.
  • these NCO-terminated disulfide compounds are reacted with hydroxyalkyl acrylates or hydroxyalkyl methacrylates, so that (meth) acrylate-terminated disulfide compounds are formed.
  • Examples of the hydroxyalkyl (meth) acrylates to be used are the corresponding ethyl, propyl or butyl compounds.
  • the (meth) acrylate-terminated disulfide compounds obtained in this way can be combined as usual with corresponding copolymerizable compounds and cured by free radical or ionic means. Examples of such copolymerizable compounds known per se are given in DE-C 19545123 column 5 lines 24 to 47.
  • the comonomers mentioned therein are expressly part of this invention.
  • epoxy-functionalized di- or polysulfides can be prepared from the NCO-terminated disulfide or polysulfide compounds by reaction with epoxy compounds containing hydroxyl groups.
  • hydroxy-functional epoxides are glycidol and the various glycidyl ethers of bisphenol A, which generally carry free hydroxyl groups.
  • the corresponding alkoxysilane-terminated products can be prepared from the NCO-terminated di- or polysulfide compounds by reaction with amino-functional alkoxysilanes.
  • Very particularly preferred structural components according to formula I are cystamine, dithiodiethanol and dithiodipropionic acid.
  • One or more compounds of the general formula can be used as a further structural component of the adhesive composition according to the invention
  • XR 3 -Y (II) Find use, where X and Y can have the meanings given above and R 3 is an at least divalent organic radical.
  • the components of the formula II are usually so-called prepolymer compounds with a molecular weight range between 300 and 20,000, preferably between 700 and 10,000.
  • Particularly preferred components according to formula II are epoxy resins, isocyanate group-containing polyurethane prepolymers, novolak resins, phenolic resins or unsaturated polyesters.
  • the above-mentioned copolymerizable olefinically unsaturated compounds can also take the place of the components according to formula II.
  • polyglycidyl ethers of polyols such as ethylene glycol, dithylene glycol, triethylene glycol, 1, 2-propylene glycol, 1, 5-pentanediol, 1, 2,6-hexanetriol, glycerol, 2,2-bis (4- hydroxycyclohexyl) propane and polyalkylene glycols such as polypropylene glycol.
  • the polyglycidyl esters of aliphatic or aromatic polycarboxylic acids, such as oxalic acid, succinic acid, glutaric acid, terephthalic acid, 2,6-naphthalenedicarboxylic acid and dimer fatty acid, are also suitable.
  • epoxy compounds are the polyglycidyl ethers of polyphenols such as bisphenol A, 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) isobutane, 1,5-dihydroxynaphthalene and novolak resins.
  • Preferred epoxy compounds include higher molecular weight resins such as the chain-extended diglycidyl ether of bisphenol A, diglycidyl ether of dimer fatty acid-extended bisphenol A and bisphenol A glycidyl ether-terminated polyether polyurethanes.
  • the adducts of epoxy resins with carboxy-, amino- and / or hydroxy-functional nitrile rubbers can also be used as the epoxy component.
  • the polyurethane prepolymers containing isocyanate groups are composed of aromatic, cycloaliphatic or aliphatic polyisocyanates and di- and / or polyols.
  • Suitable aromatic polyisocyanates are: All isomers of tolylene diisocyanate (TDI) either in isomerically pure form or as a mixture of several isomers, naphthalene-1,5-diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), diphenylmethane-2,4 ' Diisocyanate and mixtures of 4,4'-diphenylmethane diisocyanate with the 2,4'-isomer or their mixtures with higher-functional oligomers (so-called raw MDI).
  • TDI tolylene diisocyanate
  • MDI diphenylmethane-4,4'-diisocyanate
  • MDI diphenylmethane-2,4 ' Diisocyanate
  • 4,4'-diphenylmethane diisocyanate with the 2,4'-isomer or their mixtures with higher-functional oligomers
  • Suitable cycloaliphatic polyisocyanates are the hydrogenation products of the aforementioned aromatic diisocyanates such as, for example, 4,4'-dicyclohexylmethane diisocyanate (H 12 MDI), 1-isocyanatomethyl-3-isocyanato-1, 5,5-trimethyl-cyclohexane (isophorone diisocyanate, IPDI), Cyclohexane-1,4-diisocyanate, hydrogenated xylylene diisocyanate (H XDI), m- or p-tetramethylxylene diisocyanate (m-TMXDI, p-
  • TMXDI dimer fatty acid diisocyanate
  • aliphatic polyisocyanates are hexane-1,6-diisocyanate (HDI), 1,6-diisocyanato-2,2,4-trimethylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane, butane-1, 4-diisocyanate and 1, 12-dodecane diisocyanate (C DI).
  • Suitable di- and / or polyols are preferably the liquid polyhydroxy compounds having two or three hydroxyl groups per molecule, such as, for example, di- and / or trifunctional polypropylene glycols in the molecular weight range from 200 to 6000, preferably in the range from 400 to 3000 statistical and / or block copolymers of ethylene oxide and propylene oxide can also be used.
  • Another group of polyethers that are preferably used are the polytetramethylene glycols, which are produced, for example, by the acidic polymerization of tetrahydrofuran the molecular weight range of the polytetramethylene glycols is between 200 and 6000, preferably in the range from 400 to 4000.
  • liquid polyesters which are obtained by condensation of di- or tricarboxylic acids, e.g. Adipic acid, sebacic acid, glutaric acid, azelaic acid, hexahydrophthalic acid or phthalic acid with low molecular weight diols or triols such as e.g. Ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, 1, 4-butanediol, 1, 6-hexanediol, 1, 10-decanediol, glycerol or trimethylolpropane can be produced.
  • di- or tricarboxylic acids e.g. Adipic acid, sebacic acid, glutaric acid, azelaic acid, hexahydrophthalic acid or phthalic acid
  • diols or triols such as e.g. Ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, di
  • polyesters based on ⁇ -caprolactone also called “polycaprolactones”.
  • polyester polyols of oleochemical origin can also be used.
  • Such polyester polyols can, for example, by completely ring opening epoxidized triglycerides of an at least partially olefinically unsaturated fatty acid-containing fat mixture with one or more alcohols with 1 to 12 C atoms and then partial transesterification of the triglyceride derivatives to alkyl ester polyols with 1 to 12 C atoms in the alkyl radical are produced (see for example DE-A-3626223).
  • Other suitable polyols are polycarbonate polyols and dimer diols (from Henkel) and castor oil and its derivatives.
  • the hydroxyl-functional polybutadienes, such as those e.g. are available under the trade name "Poly-bd" can be used as polyols for the compositions according to the invention.
  • the low molecular weight hydroxy-functional (meth) acrylate polymers disclosed in EP-A-205846 can be used as polyols.
  • the known condensation products of phenol and / or resorzine with formaldehyde can be used as novolak resins or phenolic resins.
  • the co-condensates with terpenes, ie the terpene phenol resins, can also be used here.
  • the adhesive compositions according to the invention basically contain at least one structural component of the general formula I containing di- or polysulfide bonds and one structural component of the general formula II.
  • the two components must of course be matched to one another. Examples of useful combinations are:
  • a suitable combination of the structural components according to formula I and formula II can, however, also be in binders based on liquid rubbers which are polymerized with vulcanization systems containing sulfur and / or sulfur compounds. Specific examples of the liquid rubbers used for this are given on page 5 in WO 96/36660. Suitable sulfur-containing vulcanizing agents for this purpose are disclosed on page 6 last paragraph to page 7 first paragraph of WO 96/36660.
  • the adhesive compositions according to the invention can additionally contain plasticizers.
  • all common plasticizers can be used here, examples include the C 6 -C 14 dialkyl esters of phthalic acid, alkyl benzyl esters of phthalic acid, benzoates of di- or trifunctional polyols such as dipropylene glycol dibenzoate, alkyl sulfonic acid esters of phenol and cresol, aryl phosphates , Alkyl phosphates, C 6 -C 14 diesters of aliphatic C 4 -C 10 dicarboxylic acids and / or polymer plasticizers based on diols and dicarboxylic acids and mixtures thereof.
  • the adhesive compositions can furthermore contain fillers in amounts of between 5 and 60% by weight.
  • suitable fillers are limestone flour, natural, ground chalk (calcium carbonate or calcium magnesium carbonate), precipitated chalk, difficult to save, talc, mica, clays, soot and color pigments such as e.g. Titanium dioxide or iron oxides.
  • the adhesives according to the invention can contain further auxiliaries and additives, such as e.g. Anti-aging agents and stabilizers, rheology aids such as fumed silicas, bentones, castor oil derivatives, as well as catalysts and accelerators and, if necessary, tackifying resins.
  • auxiliaries and additives such as e.g. Anti-aging agents and stabilizers, rheology aids such as fumed silicas, bentones, castor oil derivatives, as well as catalysts and accelerators and, if necessary, tackifying resins.
  • the adhesive compositions contain inert cleaving agents under normal use. These cleavage agents have the task of cleaving the di- or polysulfide bonds built into the polymer system again. These cleavage agents are either mercapto compounds optionally with the addition of inorganic or organic basic compounds or other accelerators or they are reducing agents for reductive cleavage of the SS bonds of the adhesive. If necessary, the cleaving agents can also cause a catalytic or thermal cleavage of the SS bonds of the adhesive. If necessary, the cleavage agents can also contain further auxiliaries, in particular swelling agents, the latter facilitating and accelerating the attack of the cleavage agents by swelling of the crosslinked polymer matrix of the adhesive system.
  • mercapto compounds to be used according to the invention as cleavage reagent are 2-mercaptobenzoic acid (thiosalicylic acid), 2-mercaptobenzothiazole (2-benzothiazolethiol), 2-mercapto-benzoxazole (2-benzoxazolethiol), DL-mercapto-succinic acid (thioaepfelic acid) , 2-mercapto-4 (3H) - quinazoline, 2-mercaptoquinoline (2-quinolinethiol), 2-mercapto-1-methylimizazole, 5-mercapto-1-methyl-1 H-tetrazole, 2-mercapto-5- methyl-1, 3,4-thia-diazole, 3-mercapto-4-methyl-4H-1, 2,4-triazole, 4-mercaptophenol, 5-mercapto-3-phenyl-1, 2,4- oxadiazole, 5-mercapto-1-phenyl-1 H-tetrazole, N- (2-mercaptopro
  • cleavage reagents there are various ways to make the cleavage reagents so inert at room temperature that they allow a bond that creates a stable bond at all temperatures and is only activated when necessary.
  • One possibility is the choice of crystalline fission Reagents of the aforementioned type which have a sufficiently high melting point so that they are dispersed in the adhesive matrix in largely inert form at normal use temperatures.
  • a further possibility is the encapsulation of the cleavage reagents, this can be done in two ways, on the one hand the cleavage reagent can be encased with a separate inert capsule material, and on the other hand an encapsulation of the cleavage reagent particles can take place by an in-situ surface reaction.
  • Another possibility is the use of chemically blocked cleavage reagents and the use of topologically or sterically inactivated cleavage reagents or the use of kinetically inhibited cleavage
  • the activation of the inert cleavage reagents in the adhesive matrix can be achieved by melting, changing the conformation, accelerating the reaction (especially in the case of catalysts), triggering chemical reactions by splitting off protective groups or by in-situ generation of active centers or by capsule detonations (explosion of the inert outer layers of the microencapsulation or by Bursting of the capsule core) or by activation of cleavage catalysts which are inert at the use temperature.
  • a number of methods can be used to activate the inert cleavage reagents or inert catalysts.
  • the bonded area can be heated, on the other hand by activating heat radiation (IR radiation), by acting on particle radiation, by passing electrical current (in the case of electrically conductive adhesive formulations) and by acting on electrical and in particular electromagnetic fields Cleavage reagents are caused.
  • IR radiation heat radiation
  • IMS frequencies are available (industrial, medical, science applications).
  • Electromagnetic radiation means the approved IMS frequencies in the radio frequency range up to about 100 MHz as well as the microwaves, which are usually in the range between 0.9 and 10 GHz.
  • Another method for activating the inert cleavage reagents or inert catalysts is the use of ultrasound energy or the use of energetic pressure or shock waves.
  • releasable adhesive connections according to the invention is that normal adhesives according to the prior art are used for the joining and that a cleavable primer is used.
  • a cleavable primer is used.
  • many adhesive bonds still require primers to be applied to at least one of the substrates to be joined.
  • the primer can contain a structural component according to general formula I.
  • the primer layer can be cleaved with the cleavage agents according to the invention using the same principle of action as described above, so that the joined parts are detached in the sense of this invention without the adhesive as such being subjected to the cleavage reaction.
  • the adhesive was applied to the steel sheets so that an adhesive joint of 20 x 25 x 0.5 mm was created between the overlapping steel sheets.
  • the detackification properties were tested.
  • the glued sheets were clamped on one side in a tripod in an oven and each was loaded with 1.3 kg weight.
  • the temperature and the time at which the bonded test specimen fell apart were determined. Thereby, heating was carried out between room temperature and 50 ° C. at a heating rate of 2.5 ° C./min; between 50 ° C. and 200 ° C., the heating rate was 0.5 ° C./min.
  • the comparative example without cleavage reagent in the adhesive shows that the test specimens are still intact even at temperatures above 200 ° C. after more than 5 days, i.e. H. there was no splitting of the adhesive bond.
  • the amount of the dispersing agent dispersed can be used to control both the cleavage temperature and the time required to cleave the bond. Both fall significantly with increasing amounts of cleavage.
  • Adhesions with 1% splitting reagent were stored at a constant temperature of 80 ° C under a load of 1.3 kg, even after 10 days of continuous load no breakage of the bond was observed. Even with bonds that contained 2.5% of split agent, the bond was still intact after 5 days.
  • test specimens which had been exposed to 80 ° C for 10 days without breaking the adhesive, were further stored at 100 ° C and 120 ° C under load. No breakage occurred here either the gluing.
  • the same test specimens were then stored at 145 ° C. under load, and the bond broke after 2.5 hours. That is, a bonded test specimen where the adhesive contained 1 wt.% of this Spaltreagenzes, had at a load of 1, 3 kg 2 ⁇ A Std. are heated to 145 ° C to the adhesive matrix to split so that the bond broke.
  • the trigger temperature for the splitting of the bond depends on the proportion of the splitting agent in the adhesive formulation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne des formulations de compositions adhésives solubles à base de liants qui renferment au moins un composant structurel contenant des composés bisulfurés ou polysulfurés. Ces adhésifs peuvent être durcis par la chaleur selon les procédés classiques, soit sous forme d'adhésifs à deux composants, soit sous forme d'adhésifs thermodurcissables à un seul composant. Ces composés adhésifs peuvent être resolubilisés par des agents de séparation non dispersés, inertes à la température ambiante, à base de composés mercapto ou d'agents réducteurs, éventuellement avec adjonction de catalyseurs. Ils permettent de séparer par voie chimique, au niveau de la ligne de collage, des éléments structurels collés.
EP00909120A 1999-02-08 2000-01-29 Adhesifs solubles Withdrawn EP1161507A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1999104835 DE19904835A1 (de) 1999-02-08 1999-02-08 Lösbare Klebstoffe
DE19904835 1999-02-08
PCT/EP2000/000719 WO2000047686A1 (fr) 1999-02-08 2000-01-29 Adhesifs solubles

Publications (1)

Publication Number Publication Date
EP1161507A1 true EP1161507A1 (fr) 2001-12-12

Family

ID=7896622

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00909120A Withdrawn EP1161507A1 (fr) 1999-02-08 2000-01-29 Adhesifs solubles

Country Status (11)

Country Link
EP (1) EP1161507A1 (fr)
JP (1) JP2002536527A (fr)
AU (1) AU3151100A (fr)
BR (1) BR0008038A (fr)
CA (1) CA2362502A1 (fr)
CZ (1) CZ20012877A3 (fr)
DE (1) DE19904835A1 (fr)
MX (1) MXPA01007993A (fr)
TR (1) TR200101933T2 (fr)
WO (1) WO2000047686A1 (fr)
ZA (1) ZA200106456B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19924138A1 (de) 1999-05-26 2000-11-30 Henkel Kgaa Lösbare Klebeverbindungen
DE19951599A1 (de) 1999-10-27 2001-05-23 Henkel Kgaa Verfahren zur adhesiven Trennung von Klebeverbunden
DE10037883A1 (de) 2000-08-03 2002-02-14 Henkel Kgaa Ferromagnetische Resonanzanregung und ihre Verwendung zur Erwärmung teilchengefüllter Substrate
DE10037884A1 (de) 2000-08-03 2002-02-21 Henkel Kgaa Verfahren zur beschleunigten Klebstoffaushärtung
DE10163399A1 (de) 2001-12-21 2003-07-10 Sustech Gmbh & Co Kg Nanopartikuläre Zubereitung
FR2837114A1 (fr) * 2002-03-13 2003-09-19 Rescoll Soc Procede de separation commandee des assemblages et revetements colles et produits associes
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CZ20012877A3 (cs) 2001-12-12
DE19904835A1 (de) 2000-08-10
BR0008038A (pt) 2001-10-30
MXPA01007993A (es) 2002-04-24
CA2362502A1 (fr) 2000-08-17
JP2002536527A (ja) 2002-10-29
ZA200106456B (en) 2002-11-06
TR200101933T2 (tr) 2001-10-22
AU3151100A (en) 2000-08-29
WO2000047686A1 (fr) 2000-08-17

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