EP2094792A2 - Agent adhésif contenant un produit réactionnel du silane - Google Patents

Agent adhésif contenant un produit réactionnel du silane

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Publication number
EP2094792A2
EP2094792A2 EP06819630A EP06819630A EP2094792A2 EP 2094792 A2 EP2094792 A2 EP 2094792A2 EP 06819630 A EP06819630 A EP 06819630A EP 06819630 A EP06819630 A EP 06819630A EP 2094792 A2 EP2094792 A2 EP 2094792A2
Authority
EP
European Patent Office
Prior art keywords
formula
composition according
substrate
iii
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Withdrawn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
EP06819630A
Other languages
German (de)
English (en)
Inventor
Wolf-Rüdiger Huck
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.)
Sika Technology AG
Original Assignee
Sika Technology AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sika Technology AG filed Critical Sika Technology AG
Publication of EP2094792A2 publication Critical patent/EP2094792A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/10—Block or graft copolymers containing polysiloxane sequences
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31652—Of asbestos
    • Y10T428/31663—As siloxane, silicone or silane

Definitions

  • the present invention relates to the field of adhesion promoters, in particular the primer compositions.
  • Bonding is a widely used connection technology. Due to the large number of possible substrates which are glued together, there are always substrates that can build up with some adhesives no or insufficient adhesion. In order to improve the adhesion of adhesives and sealants to these substrates, adhesion promoters have been used for some time, especially in primers.
  • WO-A-2005/059056 describes a primer which comprises, in addition to an organotitanate and an organic solvent, a mercaptosilane and a polyaminosilane and secondary aminosilane.
  • adhesion promoters of the prior art in particular with regard to moisture-curing one-component polyurethane adhesives, frequently have adhesion problems at a low application temperature.
  • the object of the present invention is therefore to provide adhesion promoters which have good adhesions of one-component moisture-curing polyurethane adhesives, in particular on glass and glass ceramics, and in particular at low application temperatures.
  • compositions according to claim 1 can achieve this object.
  • the compositions are particularly suitable as primers for one-component moisture-curing polyurethane adhesives and are advantageously used for the bonding of glass and glass ceramic.
  • Particularly suitable they have shown in use as a primer for the glazing of means of transport, especially road vehicles.
  • compositions according to claim 1 comprise at least one
  • Reaction product obtained from a reaction mixture comprising at least one aminosilane of the formula (I)
  • R 1 here stands for an n-valent organic radical having at least one primary and / or secondary amino group.
  • R 1 stands for a m valent organic radical having at least one mercapto group.
  • R 1 is a p-valent organic radical having at least one epoxy group.
  • R 2 , R 2 and R 2 independently of one another represent an alkyl group having 1 to 4 C atoms and R 3 , R 3 and R 3 independently of one another represent H or an alkyl group having 1 to 10 C atoms.
  • a, b and c are independently of each other 0, 1 or 2 and n, m and p are independently 1, 2, 3 and 4.
  • the aminosilane, mercaptosilane and epoxysilane may thus have one or more silane groups.
  • a is 0 and R 2 is methyl or ethyl.
  • b is preferably 0 and R 2 is methyl or ethyl.
  • c is preferably 0 and R 2 is methyl or ethyl.
  • a, b and c are each 0 and R 2 , R 2 and R 2 are each methyl or ethyl, in particular methyl.
  • the indices m and p are preferably each given the value 1 and the index n is the value 1 or 2.
  • organoalkoxysilane or "SNan” for short denotes compounds in which at least one, usually two or three, alkoxy groups are bonded directly to the silicon atom (via a Si-O bond), and on the other hand have at least one directly to the silicon atom (via a Si-C bond) bound organic radical and have no Si-O-Si bonds.
  • silane group denotes the silicon-containing group bonded to the organic radical of the organoalkoxysilane
  • organoalkoxysilanes, or their silane groups have the property of hydrolyzing on contact with moisture, forming organosilanols, ie organosilicon compounds containing one or more silanol groups (Si-OH groups) and, by subsequent condensation reactions, organosiloxanes, that is, organosiloxanes containing one or more siloxane groups (Si-O-Si groups).
  • Terms such as “aiminosilane”, “epoxy silane” and “mercaptosilane” refer to silanes which have the corresponding functional group (primary amino, secondary amino or tertiary amino group, -SH, COC).
  • the aminosilane of the formula (I) preferably has at least one primary and / or secondary amino group and is preferably an aminosilane of the formula (IV), (V), (VI) or (VII):
  • R 4 is a linear or branched alkylene group having 1 to 6 C atoms, in particular propylene.
  • aminosilanes of the formula (IV), (V), (VI) or (VII) are 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 3-amino-2-methylpropyltrimethoxysilane, 4-aminobutyltrimethoxysilane, 4-amino-butyl-dimethoxymethylsilane, 4-amino-3-methylbutyl-trimethoxysilane, 4-amino-3,3-dimethylbutyl-thmethoxysilane, 4-amino-3,3-dimethylbutyl-thmethoxysilane, 4-amino-3,3-dimethylbutyl-dimethoxymethyl-silane, 2-aminoethyl-thmethoxysilane, 2-aminoethyl-dime
  • the mercaptosilane of the formula (II) is preferably a mercaptosilane of the formula (VIII):
  • R 4 is a linear or branched alkylene group having 1 to 6 C atoms, in particular propylene.
  • Mercaptosilanes of the formula (VIII) in which R 4 is propylene, b is 0 and R 2 is methyl or ethyl are particularly suitable.
  • Particularly preferred mercaptosilanes are 3-mercaptopropyl-thmethoxysilane and 3-mercaptopropyl-triethoxysilane.
  • the epoxysilane of the formula (III) is preferably an epoxysilane of the formula (IX) or (XI):
  • R 4 is a linear or branched alkylene group having 1 to 6 C atoms, in particular propylene.
  • epoxysilanes are 2- (3,4-epoxycyclohexyl) ethyl-th-methoxysilane, 2- (3,4-epoxycyclohexyl) -ethyl-thethoxysilane, 3-glycidyloxypropyl-thethoxysilane and 3-glycidyloxypropyl-thmethoxysilane.
  • the epoxy silane preferably carries a glycidyloxy group.
  • Preferred epoxysilanes are 3-glycidyloxypropyl-triethoxysilane and 3-glycidyloxypropyl-thmethoxysilane.
  • the most preferred epoxysilane is 3-glycidyloxypropyl-thmethoxysilane.
  • OH R 5 in this case represents H, a C 1 -C 20 -alkyl, cycloalkyl or aryl radical or a radical of the formula -R 4 -Si (OR 2 ) (3 - a ) (R 3 ) a and R 4 and R 4 "are independently of each other a linear or branched alkylene group having 1 to 6 C-atoms, in particular propylene.
  • the reaction product is obtained from a reaction mixture comprising aminosilane, epoxysilane and mercaptosilane.
  • the epoxysilane of the formula (III) is preferably used substoichiometrically with respect to the mercaptosilane of the formula (II).
  • the aminosilane of formula (I) which is
  • Mercaptosilane of the formula (II) and the epoxy silane of the formula (III) are used in such a ratio that the number of epoxy groups is equal to or greater than the sum of the number of mercapto groups and the number of primary amino groups. Preference is given to mercaptosilane of the formula (II) and aminosilane
  • this ratio is more than 2 or less than 0.5.
  • the aminosilane of the formula (I) and the mercaptosilane of the formula (II) are preferably initially charged and then the epoxysilane of the formula (III) is added.
  • composition may optionally have other ingredients. However, such further ingredients should not affect the storage stability of the composition.
  • additional constituents are, for example, solvents, inorganic fillers, catalysts and stabilizers, surfactants, acids, dyes, pigments and other adhesion promoter substances.
  • the composition contains a solvent.
  • organic solvents especially those having a boiling point below 100 ° C are suitable.
  • Particularly suitable as such organic solvents are hydrocarbons, ketones, carboxylic esters or alcohols. Examples of these are hexane, heptane, methyl ethyl ketone, acetone, butyl acetate, ethyl acetate, methanol, ethanol, propanol, isopropanol or butanol.
  • water is suitable as a solvent.
  • Suitable adhesion promoter substances are, in particular, tetraalkoxysilanes, organoalkoxysilanes, organotitanium compounds and organozirconium compounds, and mixtures thereof.
  • organoalkoxysilanes are in addition to the already mentioned aminosilanes, epoxy silanes and mercaptosilanes in particular (meth) acrylatosilane and vinyl silane, in particular 3- (meth) acryloxypropyl triethoxysilane, 3- (meth) acryloxypropylthmethoxysilane, vinylthmethoxysilane and vinyltriethoxysilane to call.
  • organotitanium compounds which are known to the person skilled in the art and which are used as adhesion promoters are suitable as organotitanium compounds.
  • the organotitanium compound preferably carries at least one group which hydrolyzes under the influence of water and leads to the formation of a Ti-OH group.
  • such an organotitanium compound carries at least one functional group selected from the group consisting of alkoxy group, sulfonate group, carboxylate group Acetylacetonate, or mixtures thereof, and which is bonded via an oxygen-titanium bond directly to a titanium atom.
  • neoalkoxy substituents have proven particularly suitable.
  • Particularly suitable sulfonic acids are aromatic sulfonic acids whose aromatics are substituted by an alkyl group, in particular p-dodecylbenzenesulfonic acid.
  • carboxylates of fatty acids have proved particularly suitable as carboxylate groups.
  • Preferred carboxylates are decanoate.
  • organozirconium compound basically all organozirconium compounds known to those skilled in the art which are used as adhesion promoters are suitable.
  • the organozirconium compound preferably carries at least one group which hydrolyzes under the influence of water and leads to the formation of a Zr-OH group.
  • Such an organozirconium compound preferably carries at least one functional group which is selected from the group comprising alkoxy group, sulfonate group, carboxylate group, phosphate or mixtures thereof, and which is bonded directly to a zirconium atom via an oxygen-zirconium bond.
  • Particularly suitable alkoxy groups are isopropoxy and so-called neoalkoxy substituents.
  • Particularly suitable sulfonic acids are aromatic sulfonic acids whose aromatics are substituted by an alkyl group, in particular p-dodecylbenzenesulfonic acid.
  • carboxylates of fatty acids have proved particularly suitable as carboxylate groups.
  • Preferred carboxylates are stearate.
  • Organozirconium compounds and organotitanium compounds are widely available commercially, for example from Kenrich Petrochemicals or DuPont, such as NZ 38J, NZ TPPJ, KZ OPPR, KZ TPP, NZ 01, NZ 09, NZ 12, NZ38, NZ 44, NZ 97 from Kenrich Petrochemicals, Ken- React® KR TTS, KR 7, KR 9S, KR 12, KR 26S, KR 33DS, KR 38S, KR 39DS, KR44, KR 134S, KR 138S, KR 158FS, KR212, KR 238S, KR 262ES , KR 138D, KR 158D, KR238T, KR 238M, KR238A, KR238J, KR262A, LICA 38J, KR 55, LICA1, LICA 09, LICA 12, LICA 38, LICA 44, LICA 97, LICA 99, KR OPPR, KRO
  • the composition is an aqueous composition which, in addition to the reaction product, contains water, a surfactant, and preferably an acid.
  • Particularly suitable acids are an organic acid having a pKa of less than 5.
  • organic carboxylic acids and sulfonic acids are suitable.
  • carboxylic acid are in particular those to be mentioned which are selected from the group consisting of formic, acetic, propionic, trifluoroacetic, oxalic, malonic, succinic, maleic, fumaric and citric acid and amino acids, in particular aspartic acid and glutamic acid. Preference is given to acids which have a pK a between 4.0 and 5.
  • Such acids because of their pK a, have an excellent buffering effect in the optimum pH range of 3.5 to 4.5 of the aqueous composition for the present invention.
  • Acetic acid is preferred as the carboxylic acid.
  • Organic sulfonic acids are compounds which have an organic radical having carbon atoms and at least one -SO 3 H functional group.
  • aromatic sulfonic acids which are mononuclear or polynuclear and may have one or more sulfonic acid groups.
  • these may be 1- or 2-naphthalenesulfonic acid, 1,5-naphthalenedisulfonic acid, benzenesulfonic acid or alkylbenzenesulfonic acids.
  • Preferred aromatic sulfonic acids are p-alklylbenzenesulfonic acids, in particular p-toluenesulfonic acid and p-dodecylbenzylsulfonic acid.
  • the composition is excellent as a primer and can be widely used. In particular, it can be used as a primer or as a primer component.
  • a primer is a primer understood, which is applied to a surface and after a certain waiting time after application, the so-called flash off time of an adhesive or sealant or a coating is covered and serves the adhesion of the adhesive or sealant or the coating on the substrate surface in question is improved ,
  • such a primer contains a binder which is preferably a reactive binder, especially epoxy or isocyanate based.
  • composition may also be used as a primer in an adhesive or sealant or coating.
  • Particularly suitable is the use in an adhesive or sealant.
  • a first method of bonding or sealing comprises the following steps i) application of the described composition to a substrate to be bonded or sealed S1 ii) application of an adhesive or sealant to the aerated composition which is on the substrate S1 iii) contacting the adhesive or sealant with a second one
  • a second method of bonding or sealing comprises the following steps i ') application of the described composition to a substrate to be bonded or sealed S1 ii') application of an adhesive or sealant to the surface of a second substrate S2 iii ') contacting the adhesive or Sealant having the aerated composition which is on the substrate S1;
  • a third method of bonding or sealing comprises the following steps i ") application of the described composition to a substrate S1 ii" to be bonded or sealed.) aeration of the composition iii ") application of an adhesive or sealant between the surfaces of the substrate S1 and S2.
  • the second substrate S2 is made of the same or different material as the substrate S1.
  • step iii), iii ') or iii ") typically follows
  • Step of curing the adhesive or sealant The person skilled in the art understands that, depending on the system used and reactivity of the adhesive, crosslinking reactions, and thus already curing, can already begin during the application. However, the main part of the crosslinking and thus in the narrower sense of the term curing takes place after the application, otherwise there are also problems with the buildup of adhesion to the substrate surface.
  • At least one of the substrates S1 or S2 is glass or glass ceramic.
  • one substrate is glass or glass ceramic and the other substrate is a lacquer or a lacquered metal or a lacquered metal alloy.
  • the substrate is S1, respectively S2, glass or glass ceramic and that the substrate S2, respectively S1, a paint or a painted metal or a painted metal alloy.
  • adhesives or sealants various adhesive or sealing systems can be used.
  • these are moisture-curing adhesives or sealants based on prepolymers which are terminated with isocyanate groups and / or alkoxysilane.
  • Suitable adhesives or sealants based on alkoxysilane-terminated prepolymers are one-component moisture-curing adhesives or sealants, the so-called MS polymers or alkoxysilane.
  • terminated polyurethane prepolymers in particular those prepared from polyols and isocyanates with subsequent reaction of an isocyanate-reactive organosilane or an isocyanate-functional organosilane.
  • Suitable adhesives or sealants based on isocyanate-terminated prepolymers are, on the one hand, two-component polyurethane adhesives or sealants whose first component comprises an amine or a polyol and whose second component comprises an NCO-containing prepolymer or a polyisocyanate.
  • two-component room temperature-curing polyurethane adhesives are those from SikaForce® product line, as are commercially available from Sika Nurse AG.
  • Suitable adhesives or sealants based on isocyanate-terminated prepolymers are reactive polyurethane hotmelt adhesives or sealants which comprise a thermoplastic polymer and an isocyanate-terminated prepolymer or a thermoplastic isocyanate-terminated prepolymer.
  • reactive polyurethane hotmelts are melted and solidify on the one hand during cooling and on the other hand crosslink via a reaction with atmospheric moisture.
  • Suitable adhesives or sealants based on isocyanate-terminated prepolymers furthermore include one-component moisture-curing polyurethane adhesives. Such adhesives or sealants crosslink under the influence of moisture, in particular of
  • Polyurethane adhesives are those of the SikaFlex® and SikaTack® product line, as are commercially available from Sika Nurse AG.
  • the above-mentioned isocyanate-terminated prepolymers are prepared from polyols, in particular polyoxyalkylene polyols, and polyisocyanates, especially diisocyanates.
  • Polyurethane adhesives or sealants greatly improve the adhesion at low temperatures, ie in particular one
  • the most preferred application is the vitrification of means of transport, in particular of road and rail vehicles to call.
  • this method is particularly suitable for repair glazing. Namely, vehicles can be glazed on the road on site, especially in winter, without the vehicle must first be placed in a temperature controlled garage. This is especially important for repairs of vehicle windows, in sprawling areas, especially where the roads often have loose stones or gravel. Such areas are frequently found, for example, in Scandinavia, Russia, China, Argentina, Chile, Canada or the USA. Examples
  • compositions according to Tables 2 and 3 were prepared by, if used, the aminosilane and the mercaptosilane was initially charged, and then with stirring, if present, the epoxysilane was slowly added. Subsequently, it was stirred for 4 days and
  • compositions were the following grounds using soaked lint-free Kleenex® cloth at the application temperature ( “Tapp”) of 23 ° C and -1 0 ° C is applied and during the flash-off time ( “IP”) flashed off "disk 1": Windshield an Audi A4 (Sigla) (application on
  • compositions and the substrates were conditioned at the application temperature for at least 12 hours.
  • Ref.1 is Sika® activator, commercially available from Sika Nurse AG.
  • SikaTack®-Move Goes Cool were applied as a triangular bead (12 mm base, 8 mm height) and baked to a layer thickness of 4 mm compressed.
  • the adhesive was cured as follows:
  • the adhesion of the adhesive was tested by means of a 'bead test'. This is cut at the end just above the adhesive surface. The cut end of the caterpillar is held with a pair of pliers and pulled from the ground. This is done by carefully rolling up the bead on the nipper tip, and placing a cut to the bare ground perpendicular to the caterpillar pulling direction. The caterpillar pull-off speed should be selected so that a cut must be made approx. Every 3 seconds. The test track must be at least 8 cm. The adhesive that remains after the removal of the caterpillar from the substrate (cohesive failure) is assessed. The assessment of the adhesive properties is carried out by estimating the cohesive part of the adhesive surface:
  • compositions according to the invention are very suitable as adhesion promoters. Furthermore, the beneficial effect of the secondary aminosilanes over the primary aminosilanes is shown.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des compositions qui contiennent ou sont composées d'un produit réactionnel obtenu à partir d'un mélange réactionnel contenant un aminosilane de formule (I), un mercaptosilane de formule (II) et un époxysilane de formule (III). Les compositions conviennent en tant qu'agents adhésifs, en particulier sous la forme d'amorces. Ils se caractérisent par une bonne adhérence et conviennent en particulier à des applications à basse température, et plus particulièrement au collage de verre.
EP06819630A 2006-11-20 2006-11-20 Agent adhésif contenant un produit réactionnel du silane Withdrawn EP2094792A2 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2006/068680 WO2008061556A2 (fr) 2006-11-20 2006-11-20 Agent adhésif contenant un produit réactionnel du silane

Publications (1)

Publication Number Publication Date
EP2094792A2 true EP2094792A2 (fr) 2009-09-02

Family

ID=39430085

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06819630A Withdrawn EP2094792A2 (fr) 2006-11-20 2006-11-20 Agent adhésif contenant un produit réactionnel du silane

Country Status (4)

Country Link
US (1) US8263185B2 (fr)
EP (1) EP2094792A2 (fr)
CN (1) CN101605857B (fr)
WO (1) WO2008061556A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4039764A4 (fr) * 2019-10-02 2023-10-18 KCC Corporation Composition d'apprêt pour adhésif de verre

Families Citing this family (16)

* Cited by examiner, † Cited by third party
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PL2110420T3 (pl) * 2008-04-11 2011-03-31 Sika Tech Ag Sposób nanoszenia na podłoże zestawu zwiększającego przyczepność
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US20100323203A1 (en) 2010-12-23
CN101605857A (zh) 2009-12-16
CN101605857B (zh) 2012-08-08
WO2008061556A2 (fr) 2008-05-29
WO2008061556A3 (fr) 2008-09-12

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