EP4308616A1 - Zusammensetzung auf basis von (meth)acrylatmonomeren - Google Patents

Zusammensetzung auf basis von (meth)acrylatmonomeren

Info

Publication number
EP4308616A1
EP4308616A1 EP22714479.7A EP22714479A EP4308616A1 EP 4308616 A1 EP4308616 A1 EP 4308616A1 EP 22714479 A EP22714479 A EP 22714479A EP 4308616 A1 EP4308616 A1 EP 4308616A1
Authority
EP
European Patent Office
Prior art keywords
chosen
weight
composition
component
composition according
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
EP22714479.7A
Other languages
English (en)
French (fr)
Inventor
Jérôme MAZAJCZYK
Stéphane Fouquay
Frédéric Simon
Guillaume Michaud
Alexis BARRAT
Jacques Lalevee
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.)
Centre National de la Recherche Scientifique CNRS
Bostik SA
Universite de Haute Alsace
Original Assignee
Centre National de la Recherche Scientifique CNRS
Bostik SA
Universite de Haute Alsace
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
Priority claimed from FR2102661A external-priority patent/FR3120871B1/fr
Application filed by Centre National de la Recherche Scientifique CNRS, Bostik SA, Universite de Haute Alsace filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP4308616A1 publication Critical patent/EP4308616A1/de
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
    • 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
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/10—Esters
    • C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F120/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • C09D133/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—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
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters

Definitions

  • the present invention relates to a composition based on (meth)acrylate monomer.
  • the invention also relates to the use of said composition for repairing and/or semi-structural or structural bonding of materials in the field of transport, marine, assembly, electronics or construction.
  • Acrylic compositions are known reactive systems that crosslink by radical polymerization. They are used as adhesives, sealants and coatings. Radical polymerization is typically initiated by a redox system which, through an oxidation-reduction reaction, leads to the production of radicals.
  • the majority of acrylic systems are two-component systems.
  • the first component traditionally contains the reducing agent and the reactive monomers, and the second component contains the oxidizing agent. Once the two components are mixed, the reducing agent induces the cleavage of the 0-0 bond of the organic peroxide, for example, and initiates the polymerization.
  • the (meth)acrylic compositions comprise a redox system of the peroxide (oxidant)/tertiary amine (reductant) type.
  • these systems can present stability problems with respect to storage in the presence of (meth)acrylate monomer.
  • the present invention relates to a crosslinkable two-component composition
  • a component A comprising:
  • each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R a , and R b represents, independently of each other, a radical selected from the group consisting of hydrogen, halogen, alkyl, cycloalkyl or aryl;
  • Rf represents perhaloalkyl or haloalkyl
  • X represents an anion
  • R 10 represents H, methyl or ethyl
  • - Z represents H, O, S, an alkyl group, a benzyl group, an aryl group, or an alkoxy group;
  • - Y represents O, S, NH or CH 2 ; is a single bond or a double bond, provided that when Z represents O, then the bond is a double bond;
  • component B comprising at least one compound having the following formula (V):
  • R c represents a radical chosen from: a heteroaryl, an aryl, an alkyl, the said heteroaryl, aryl and alkyl being optionally substituted by at least one of the following radicals: F, OH, C(0)OMe, NHC(0) Me, methyl (Me), CF 3, OH or S0 2 -;
  • Q + represents a cation chosen from Li + , Na + or K + .
  • alkyl is understood to mean a linear or branched radical preferably comprising from 1 to 20 carbon atoms. Mention may be made, for example, of methyl, ethyl and propyl.
  • aryl is understood to mean a monocyclic or bicyclic aromatic radical preferably comprising from 6 to 12 carbon atoms. Mention may be made, for example, of phenyl.
  • cycloalkyl means a monocyclic or polycyclic system, preferably mono or bicyclic, saturated, preferably comprising from 3 to 12 carbon atoms, the rings possibly being fused or bridged in pairs. , such as cyclopropyl, cyclopentyl, cyclohexyl or norbornyl groups.
  • alkoxy means an -O-alkyl radical
  • Component A comprises a compound of formula (Ia) or (Ib) as defined above.
  • the anion X can be selected from the group consisting of FSO3, CF3SO3, CF2HSO3, Ch, Br, BF 4 -, BF3Cl-, PF 6 -.
  • Rf may represent haloalkyl. It may for example be a fluoroalkyl radical, such as for example CHF 2 or CH 2 F.
  • Rf represents a perfluoroalkyl, and even more preferably CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9 . According to a particularly preferred embodiment, Rf represents CF 3 .
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 , R a and R b represents, independently of each other, a radical chosen from the group consisting of a hydrogen atom, a halogen, or an alkyl, preferably a hydrogen or a fluorine atom;
  • Rf represents a perfluoroalkyl or a fluoroalkyl, preferably a perfluoroalkyl
  • - X represents an anion, preferably chosen from FSO 3 , CFsSCb and BF 4 .
  • component A comprises a compound of formula (Ia), in particular chosen from the group consisting of: 3 3 and even more preferably from one of the following compounds:
  • the compounds of formula (la) can be prepared as described in WO 2016/107578.
  • the compounds of formula (Ib) can be prepared as described in WO2011/013307.
  • the total content of compound(s) of formula (Ia) or (Ib) can range from 0.05% to 5.0% by weight, preferably from 0.1% to 3.0% by weight, even more preferably from 0.1% to 1.5% by weight relative to the total weight of the crosslinkable two-component composition.
  • Component A according to the invention comprises at least one (meth)acrylate monomer M1 having one of the following formulas (II), (III) or (IV): in which :
  • - R 10 represents H, methyl or ethyl
  • - p represents 0 or 1
  • - Z represents H, O, S, an alkyl group, a benzyl group, an aryl group, or an alkoxy group;
  • - Y represents O, S, NH or Chh; is a single bond or a double bond, provided that when Z represents O, then the bond is a double bond.
  • the (meth)acrylate monomer M1 can be chosen from the following monomers:
  • the monomer M1 is preferably chosen from the monomers of formula (II) or (III).
  • the total content of (meth)acrylate monomer(s) M1 in component A may be greater than or equal to 30% by weight relative to the total weight of said component A.
  • the content of (meth)acrylate monomer(s) M1 in the crosslinkable two-component composition according to the invention can range from 30% to 99% by weight, preferably from 50% to 99% by weight, even more preferably from 75% to 99% by weight relative to the total weight of said crosslinkable two-component composition.
  • Component B comprises at least one compound having the following formula (V):
  • R c represents a radical chosen from: a heteroaryl, an arylalkyl, an aryl, an alkyl, the said heteroaryl, arylalkyl, aryl and alkyl being optionally substituted by at least one of the following radicals: F, OH, C(0)0Me , NHC(0)Me, methyl (Me), CF 3, OH or S0 2 -;
  • Q + represents a cation chosen from Li + , Na + or K + .
  • the compound of formula (V) is chosen from those for which:
  • Q + preferably representing Na + or K + , and even more preferably Na + , - R c represents a radical chosen from a heteroaryl or an aryl.
  • the compound of formula (V) can be chosen from the following compounds: According to a preferred embodiment, the compound of formula (V) is chosen from the following compounds:
  • the total content of compound(s) of formula (V) as defined above can range from 0.05% to 5.0% by weight.
  • the total content of compound(s) of formula (V) as defined above can range from 0.1% to 5.0% by weight, preferably from 0.1% to 3.0% by weight, and even more preferably from 0.1% to 1.5% by weight relative to the total weight of the crosslinkable two-component composition according to the invention.
  • the compound(s) of formula (I)/compound(s) of formula (V) molar ratio can range from 0.01 to 1.2, preferably from 0.02 to 1.1, preferably from 0.04 to 1.0 and even more preferably from 0.08 to 0.8.
  • the crosslinkable two-component composition does not include peroxide.
  • the two-component composition according to the invention does not comprise alkyl(meth)acrylate, such as for example methyl(meth)acrylate, nor benzyl(meth)acrylate.
  • the crosslinkable two-component composition according to the invention may comprise at least one additive chosen from the group consisting of catalysts, fillers, antioxidants, light stabilizers/UV absorbers, metal deactivators, antistatic agents, antifogging agents , foaming agents, biocides, plasticizers, lubricants, emulsifiers, colorants, pigments, rheological agents, impact modifiers, adhesion promoters, optical brighteners, flame retardants, anti- ooze, nucleating agents, solvents, polymerization inhibitors, and mixtures thereof.
  • additives may be present in component A and/or component B of the composition according to the invention.
  • adhesives such as, for example, epoxy resins, phthalates, benzoates, trimethylolpropane esters, trimethylolethane esters , trimethylolmethane esters, glycerol esters, pentaerythritol esters, napthenic mineral oils, adipates, cyclohexyldicarboxylates
  • diisodecyl phthalate such as for example marketed under the name PALATINOLTM DIDP by the company BASF
  • an ester of alkylsulphonic acid and phenol such as for example marketed under the name MESAMOLL® by the company LANXESS
  • diisononyl-1,2-cyclohexanedicarboxylate such as for example marketed under the name HEXAMOLL DINCH® by the company BASF
  • pentaerythritol tetravalerate such as for example marketed under the name PEVALENTM by the company PERSTORP
  • the oil of Epoxidized soybean such as, for example, marketed under the name VIKOFLEX® 7170 by the company ARKEMA.
  • (thixotropic) rheology agent(s) that can be used, mention may be made of any rheology agent usually used in the field of adhesive compositions.
  • the thixotropic agents are chosen from: PVC plastisols, corresponding to a suspension of PVC in a plasticizer miscible with PVC, obtained in situ by heating at temperatures ranging from 60°C to 80°C.
  • PVC plastisols can be those described in particular in the work “Polyurethane Sealants”, Robert M. Evans, ISBN 087762-998-6, fumed silica, such as for example sold under the name HDK® N20 by WACKER; urea derivatives resulting from the reaction of an aromatic diisocyanate monomer such as 4,4'-MDI with an aliphatic amine such as butylamine.
  • urea derivatives is described in particular in application FR 1 591 172; micronized amide waxes, such as CRAYVALLAC® SLT or CRAYVALLAC® SLA marketed by ARKEMA.
  • composition according to the invention may also comprise at least one organic and/or mineral filler.
  • the mineral filler(s) that can be used is (are) advantageously chosen so as to improve the mechanical performance of the composition according to the invention in the crosslinked state.
  • any mineral filler(s) usually used in the field of adhesive compositions can be used.
  • These fillers are typically in the form of particles of various geometry. They can be for example spherical, fibrous, or have an irregular shape.
  • the filler(s) is (are) chosen from the group consisting of clay, quartz, carbonate fillers, kaolin, gypsum, clays, and mixtures thereof, preferably the filler(s) is (are) chosen from carbonate fillers, such as alkali or alkaline-earth metal carbonates, and more preferably calcium carbonate or chalk.
  • These fillers can be untreated or treated, for example using an organic acid such as stearic acid, or a mixture of organic acids mainly consisting of stearic acid.
  • hollow mineral microspheres such as hollow glass microspheres, and more particularly those made of sodium and calcium borosilicate or of aluminosilicate.
  • composition according to the invention may also comprise at least one adhesion promoter, preferably chosen from silanes, such as aminosilanes, epoxysilanes or acryloyl silanes, or adhesion promoters based on phosphate ester such as for example 2-hydroxyethyl methacrylate phosphate ester, 2-methacryloyloxyethyl phosphate, bis-(2-methacryloyloxyethyl phosphate), 2-acryloyloxyethyl phosphate, bis-(2-acryloyloxyethyl phosphate), methyl-( 2-methacryloyloxyethyl phosphate), ethyl-(2- methacryloyloxyethyl phosphate), a mixture of mono and di-phosphate esters of 2-hydroxyethyl methacrylate.
  • silanes such as aminosilanes, epoxysilanes or acryloyl silanes
  • a pigment When a pigment is present in the composition, its content is preferably less than or equal to 3% by weight, more preferably less than or equal to 2% by weight, relative to the total weight of the composition. When it is present, the pigment can for example represent from 0.1% to 3% by weight or from 0.4% to 2% by weight of the total weight of the composition.
  • the pigments can be organic or inorganic pigments.
  • the pigment is T1O2, in particular KRONOS® 2059 marketed by the company KRONOS.
  • TEMPOL 4-hydroxy-2, 2,6,6-tetramethylpiperidinoxyl or TEMPOL (CAS: 2226-96-2) marketed by the companies BASF and EVONIK.
  • the composition may comprise an amount of 0.1% to 3%, preferably 1% to 3% by weight, of at least one UV stabilizer or antioxidant.
  • UV stabilizer or antioxidant typically introduced to protect the composition from degradation resulting from a reaction with oxygen which is likely to be formed by the action of heat or light.
  • These compounds can include primary antioxidants that scavenge free radicals. Primary antioxidants can be used alone or in combination with other secondary antioxidants or UV stabilizers.
  • IRGANOX® 1010 Mention may be made, for example, of IRGANOX® 1010, IRGANOX® B561, IRGANOX® 245, IRGAFOS® 168, TINUVIN® 328 or TINUVINTM 770 marketed by BASF.
  • the crosslinkable two-component composition can also comprise a radical photoinitiator which can be found in component A and/or component B of the composition.
  • This radical photo-initiator is in particular a compound additional to the ingredients of the two-component composition as claimed.
  • composition according to the invention may comprise from 0.1% to 5% by weight, preferably from 0.5% to 3% by weight, even more preferably from 0.5% to 1.5% by weight, of photo -radical initiator(s) relative to the total weight of the composition.
  • the radical photoinitiator is preferably contained in component A.
  • the radical photo-initiator can be any radical photo-initiator known to those skilled in the art. Under the action of UV-visible radiation, the radical photo-initiator generates radicals which will be responsible for initiating the photo-polymerization reaction, and in particular makes it possible to increase the efficiency of the photo-polymerization reaction . This is of course chosen according to the light source used, according to its ability to effectively absorb the selected radiation. It is possible, for example, to choose the appropriate radical photoinitiator from its visible UV absorption spectrum.
  • the radical photo-initiator is suitable for working with irradiation sources emitting in the near-visible zone.
  • the source of the UV or visible radiation can be an LED or UVA-focused broad-spectrum lamp of the DELOLUX 03 S type.
  • the radical photo-initiator can be chosen from the group consisting of:
  • acetophenones and alkoxyacetophenones such as for example 2,2-dimethoxy-2-phenylacetophenone and 2-diethyl-2-phenylacetophenone;
  • hydroxyacetophenone family such as for example 2,2-dimethyl-2-hydroxyacetophenone, 1-hydroxycyclohexylephenyl ketone, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methyl-propriophenone and 2- hydroxy-4'-(2-hydroxypropoxy)-2-methyl-propophenone;
  • alkylaminoacetophenones such as for example 2-methyl-4'-(methylthio)-2-morpholino-propriophenone, 2-benzyl-2-(dimethylamino)-4-morpholinobutyrophenone and 2-(4-( methylbenzyl)-2-(dimethylamino)-4-morpholino-butyrophenone;
  • benzoin ethers such as for example benzyl, methyl ether of benzoin and isopropyl ether of benzoin;
  • phosphine oxides such as for example diphenyl oxide-(2,4,6-trimethylbenzoyl)phosphine (TPO), ethyl oxide-(2,4,6-trimethylbenzoyl)phenylphosphine ( TPO-L) and bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylphenyl phosphine oxide (BAPO);
  • the metallocene family such as for example ferrocene, bis(eta 5-2,4-cyclopentadiene-1-yl)-bis(2,6-difluoro)-3-(1H-pyrrole-1-yl) -phenyl) titanium and iron (cumene) cyclopentadienyl hexafluorophosphate;
  • benzophenones such as for example 4-phenylbenzophenone, 4- (4'-methylphenylthio)benzophenone, 1-[4[ (4-benzoylphenyl)thio]phenyl]-2-methyl-2-[( 4-methylphenyl)sulfonyl]-1-propanone;
  • thioxanthones such as for example isopropylthioxanthone (ITX), 2,4-diethylthioxanthone, 2,4-dimethylthioxanthone, 2-chlorothioxanthone and 1-chloro-4-isopropylthioxanthone;
  • dibenzylidene ketones such as for example p-dimethylaminoketone
  • coumarin family such as for example 5-methoxy and 7-methoxy coumarin, 7-diethylamino coumarin and N-phenylglycine coumarin
  • - radical photo-initiators of the family of dyes such as for example triazines, fluorones, cyanines, safranins, 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4 ',5'-7'-tetraiodo-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one, pyrylium and thiopyrylium, thiazines, flavins, pyronines, oxazines, rhodamines;
  • the radical photo-initiator is chosen from the family of phosphine oxides, such as for example diphenyl-(2,4,6-trimethylbenzoyl)phosphine oxide (TPO), ethyl oxide-( 2,4,6-trimethylbenzoyl)phenylphosphine (TPO-L) and bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylphenyl phosphine oxide (BAPO).
  • TPO diphenyl-(2,4,6-trimethylbenzoyl)phosphine oxide
  • TPO-L ethyl oxide-( 2,4,6-trimethylbenzoyl)phenylphosphine
  • BAPO bis-(2,6-dimethoxybenzoyl)-2,4,4-trimethylphenyl phosphine oxide
  • the radical photo-initiator can be chosen from 2,4,6-trimethylbenzoyldiphenylphosphine or TPO available for example from LAMBSON under the trade reference SPEEDCURE® TPO ( CAS: 75980-60-8), ethyl (2,4,6-trimethylbenzoyl) phenyl phosphinate or TPO-L available for example from LAMBSON under the trade reference SPEEDCURE® TPO-L (CAS: 84434-11-7), Phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide or BAPO (CAS: 162881-26-7) available for example from BASF under the trade reference IRGACURE® 819, 2-Benzyl-2-dimethylamino-1-(4 -morpholinophenyl)-1-butanone (CAS: 119313-12-1) available for example from BASF under the trade reference IRGACURE® 369, 2-methyl-1-[4-(
  • the total content of compound(s) of formula (Ia) or (Ib) can range from 0.05% to 5.0% by weight, preferably from 0 0.05% to 3.0% by weight, more preferably from 0.05% to 1.0% by weight, even more preferably from 0.05% to 0.5% by weight and the total content of compound(s) ) of formula (V) can range from 0.05% to 5.0% by weight, preferably from 0.05% to 3.0% by weight, more preferably from 0.05% to 1.0% by weight, and even more preferably from 0.05% to 0.5% by weight relative to the total weight of the crosslinkable two-component composition according to the invention.
  • the composition according to the invention does not include peroxide.
  • the component A/component B volume ratio can range from 20/1 to 1/1, preferably from 10/1 to 1/1.
  • the present invention also relates to a ready-to-use kit, comprising component A as defined above on the one hand and component B as defined above on the other hand, packaged in two separate compartments. It may, for example, be a two-component cartridge.
  • composition according to the invention can be in a two-component form, for example within a ready-to-use kit, comprising component A on the one hand in a first compartment or barrel and component B d on the other hand in a second compartment or drum, in proportions suitable for direct mixing of the two components, for example using a metering pump.
  • the kit further comprises one or more means allowing the mixing of components A and B.
  • the mixing means are chosen from metering pumps, static mixers with a diameter adapted to the quantities used.
  • the present invention also relates to the use of a crosslinkable two-component composition as defined above, as an adhesive, putty or coating, preferably as an adhesive.
  • the invention also relates to the use of said composition for repairing and/or structural or semi-structural bonding of materials in the field of transport, automotive (car, bus or truck), assembly, marine, electronics, or construction.
  • the present invention relates to a method for assembling two substrates by bonding, comprising: the coating on at least one of the two substrates to be assembled of a composition obtained by mixing components A and B as defined above; then the effective contacting of the two substrates; the crosslinking of the composition.
  • the crosslinking step can be implemented at a temperature between 0°C and 200°C, preferably between 10°C and 150°C, preferably between 23 and 80°C and in particular between 20°C and 25°C.
  • Suitable substrates are, for example, inorganic substrates such as concrete, metals or alloys (such as aluminum alloys, steel, non-ferrous metals and galvanized metals); or else organic substrates such as wood, plastics such as PVC, polycarbonate, PMMA, polyethylene, polypropylene, polyesters, epoxy resins; metal substrates and composites coated with paint.
  • the crosslinking can be done under electromagnetic irradiation such as for example with a source of UV radiation or with an LED.
  • the step of crosslinking under electromagnetic irradiation can be carried out at a wavelength greater than 300 nm, preferably ranging from 360 nm to 680 nm, and even more preferably from 360 nm to 420 nm.
  • compositions according to the invention are advantageously stable on storage.
  • compositions according to the invention advantageously lead to a good compromise between storage stability and high reactivity.
  • compositions according to the invention advantageously exhibit, after crosslinking, good adhesive properties.
  • the surface of the crosslinked compositions advantageously dries quickly and may not be “tacky”, which makes it possible in particular to increase the productivity of industrial processes.
  • between x and y or “ranging from x to y”, is meant an interval in which the limits x and y are included.
  • the range “between 0% and 25%” includes the values 0% and 25% in particular.
  • - SR® 531 cyclic trimethylolpropane formal acrylate (CAS: 66492-51-1) marketed by ARKEMA;
  • component A In a mixer maintained under constant agitation and under nitrogen, the ingredients of component A are mixed in the proportions indicated in the following table at a temperature of 23°C.
  • Component A and component B are mixed, in a 1:1 volume ratio using a Sulzer® mixpac mixer at room temperature 23°C.
  • Example 2 Preparation of Composition No. 2 In a mixer maintained under constant agitation and under nitrogen, the ingredients of component A are mixed in the proportions indicated in the following table at a temperature of 23°C.
  • Component A and component B are mixed, in a 1:1 volume ratio using a Sulzer® mixpac mixer at room temperature 23°C.
  • component A In a mixer maintained under constant agitation and under nitrogen, the ingredients of component A are mixed in the proportions indicated in the following table at a temperature of 23°C.
  • Component A and component B are mixed, in a 1:1 volume ratio using a Sulzer® mixpac mixer at room temperature 23°C.
  • component A In a mixer maintained under constant agitation and under nitrogen, the ingredients of component A are mixed in the proportions indicated in the following table at a temperature of 23°C. In a mixer maintained under constant stirring and under nitrogen, the various ingredients constituting component B are mixed in the proportions indicated in the following table at a temperature of 23°C. Component A and component B are mixed, in a 1:1 volume ratio using a Sulzer® mixpac mixer at room temperature 23°C.
  • component A In a mixer maintained under constant agitation and under nitrogen, the ingredients of component A are mixed in the proportions indicated in the following table at a temperature of 23°C. In a mixer maintained under constant stirring and under nitrogen, the various ingredients constituting component B are mixed in the proportions indicated in the following table at a temperature of 23°C.
  • Component A and component B are mixed, in a 1:1 volume ratio using a Sulzer® mixpac mixer at room temperature 23°C.
  • Example 6 Preparation of Composition No. 6 (Comparative Example) In a mixer kept under constant stirring and under nitrogen, the ingredients of component A are mixed in the proportions indicated in the following table at a temperature of 23°C.
  • Component A and component B are mixed, in a 1:1 volume ratio using a Sulzer® mixpac mixer at room temperature 23°C.
  • Example 7 composition performance
  • the reactivity is continuously analyzed using a pyrometer and thermal imaging.
  • the gel time (or lag time) is the time it takes for the sample to start polymerizing.
  • the time/temperature profiles were carried out using an Omega OS552-V1-6 industrial infrared thermometer (Omega Engineering®, Inc., Stamford, CT) with an accuracy of ⁇ 1°C for 2 g (about 4.0 mm height) and 0.25 g (1.4 mm height) of polymerization.
  • compositions no. 1, no. 2 and no. 3 advantageously polymerize rapidly (after mixing components A and B), in view of the gel times which are short (48. 180 and 60 seconds respectively).
  • the comparative compositions n°4 and n°5 do not polymerize in the open air.
  • Composition no. 6 polymerizes but unlike parts B of examples no. 1, 2 and 3, part B is not stable over time (24 hours) and polymerizes, which makes composition no. 6 unusable in practice for a commercial product.
  • comparative composition No. 6 leads to a high gel time: 246 s compared to compositions 1, 2 and 3 according to the invention.
  • compositions No. 1 and No. 2 and No. 3 advantageously lead to bondings having fast setting times compared to composition No. 4 which does not allow bonding.

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polymerization Catalysts (AREA)
EP22714479.7A 2021-03-17 2022-03-16 Zusammensetzung auf basis von (meth)acrylatmonomeren Pending EP4308616A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR2102661A FR3120871B1 (fr) 2021-03-17 2021-03-17 Composition à base de monomères (méth)acrylate
FR2105517A FR3120872B1 (fr) 2021-03-17 2021-05-27 Composition à base de monomères ( méth )acrylate
PCT/FR2022/050473 WO2022195221A1 (fr) 2021-03-17 2022-03-16 Composition a base de monomeres (meth)acrylate

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US3547848A (en) 1967-11-03 1970-12-15 Armour Ind Chem Co Thixotropic coating compositions comprising a varnish and a di-substituted urea
US20040265733A1 (en) * 2003-06-30 2004-12-30 Houlihan Francis M. Photoacid generators
US7026367B2 (en) * 2003-09-26 2006-04-11 3M Innovative Properties Company Photoiniators having triarylsulfonium and arylsulfinate ions
US8703969B2 (en) 2009-07-28 2014-04-22 Nagoya Institute Of Technology Trifluoromethylthiophenium derivative salt, method for producing the same, and method for producing trifluoromethyl-containing compounds using the same
WO2016107578A1 (en) 2014-12-31 2016-07-07 Zhejiang Jiuzhou Pharmaceutical Co., Ltd. Halogenated s-(perfluoroalkyl) dibenzothiophenium salt and its production methods
JP6836886B2 (ja) * 2016-11-25 2021-03-03 三星エスディアイ株式会社ＳＡＭＳＵＮＧ ＳＤＩ Ｃｏ．， ＬＴＤ． 光学フィルム用接着剤
JP2020152718A (ja) * 2019-03-13 2020-09-24 住友化学株式会社 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法
FR3094375B1 (fr) * 2019-03-28 2022-04-29 Bostik Sa Composition à base de monomère méthacrylate

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