EP1237982A1 - Durch bestrahlung härtbare klebstoffzusammensetzung für kunstoff - Google Patents

Durch bestrahlung härtbare klebstoffzusammensetzung für kunstoff

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Publication number
EP1237982A1
EP1237982A1 EP00981418A EP00981418A EP1237982A1 EP 1237982 A1 EP1237982 A1 EP 1237982A1 EP 00981418 A EP00981418 A EP 00981418A EP 00981418 A EP00981418 A EP 00981418A EP 1237982 A1 EP1237982 A1 EP 1237982A1
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EP
European Patent Office
Prior art keywords
radical
carbon atoms
formula
group
linear
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.)
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Application number
EP00981418A
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English (en)
French (fr)
Inventor
Jean-Marc Frances
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.)
Rhodia Chimie SAS
Original Assignee
Rhodia Chimie SAS
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Filing date
Publication date
Application filed by Rhodia Chimie SAS filed Critical Rhodia Chimie SAS
Publication of EP1237982A1 publication Critical patent/EP1237982A1/de
Withdrawn legal-status Critical Current

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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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • 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
    • 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
    • C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • the field of the invention is that of adhesives for crosslinkable plastics and / or polymé ⁇ sables under irradiation, in particular under UV irradiation and / or by electron beam, usable, in particular, to durably assemble two surfaces in vis-
  • Plastics are increasingly used as packaging materials such as cases and pouches These plastics can be transparent, translucent, colored or opaque and are generally based on polyethylene or polypropylene The nature of the plastics and the shape of the packaging generally require the use of various technologies based on the use of adhesives or the thermofusion technique to secure the different parts of said packaging
  • the present invention proposes to overcome the existing shortcomings in the field of the assembly of two facing plastic surfaces, in particular to improve the solidarity between said surfaces in contact.
  • One of the essential objectives of the present invention is therefore to provide new adhesives based on photopolymerizable and / or photoreticulable compositions by cationic and / or radical route which meet these expectations
  • Another objective of the present invention is to provide new adhesives for easy implementation using irradiation technologies, in particular UV, and or electron beam
  • the present invention therefore relates to the use of a polymerizable and / or crosslinkable adhesive under irradiation and / or under electron beam (s), by cationic and / or radical route, to assemble two plastic surfaces facing each other.
  • a polymerizable and / or crosslinkable adhesive under irradiation and / or under electron beam (s), by cationic and / or radical route, to assemble two plastic surfaces facing each other.
  • At least one organic matrix B and / or polymerizable silicone and / or at least partially polymerized comprising (co) monomers, (co) ol ⁇ gomers and / or (co) polymers chosen from those having reactive functions (frB) epoxy ( ⁇ -
  • the matrix A with reactive oxetane functions (frA) used within the composition according to the invention can be based on (co) monomers, (co) ol ⁇ gomers and / or (co) polymers of very varied natures On this subject , are suitable in particular the (co) monomers, the (co) ol ⁇ gomers and / or the following (co) polymers consisting of at least one of the following species.
  • - Ri is (i) a hydrogen atom, (n) a linear or branched alkyl radical comprising from 1 to 30 carbon atoms, (m) an aryl radical comprising from 6 to 30 carbon atoms optionally substituted by at least one fluorine atom, a carboxy radical, a hydroxy radical, an ester radical or a radical with a ketone function, (iv) a cycloalkyl radical comprising from 5 to 6 carbon atoms optionally substituted by at least one fluorine atom, a hydroxy radical , a carboxy radical, an ester radical or a radical with a ketone function, (v) an OR 'radical where R' is a linear or branched alkyl radical comprising from 1 to 30 carbon atoms, or (vi) an alkenyl radical comprising from 2 to 12 carbon atoms
  • R 2 is (i) a hydrogen atom; (n) an alkenyl radical comprising from 2 to 12 carbon atoms (for example a vinyl radical, a propenyl radical), (m) a linear or branched alkyl radical comprising from 1 to 30 carbon atoms optionally substituted, for example, by a group oxirane, ( ⁇ v) an aryl radical comprising from 6 to 30 carbon atoms optionally substituted, for example, by at least one alkyl radical comprising from 1 to 30 carbon atoms, a benzyl radical, a CF 3 radical, a halogen atom, a hydroxy radical, a carboxy radical, an alkoxy radical, (v) a silyl group (CH2) n-S ⁇ R 3 R 4 R 5 or n is between 0 and 12, and R 3 , R ⁇ and R 5 , identical or different, represent a hydrogen atom, a hydroxy radical, an alkoxy radical OR 'where R' is a linear or
  • a divalent radical is (i) a linear or branched alkyl radical comprising from 1 to 30 carbon atoms, (n) an aryl radical comprising from 6 to 30 carbon atoms optionally substituted (by at least one alkyl radical comprising from 1 to 30 carbon atoms, (ni) an aryl radical comprising from 6 to 30 carbon atoms (for example a benzyl radical), (iv) a cycloalkyl radical comprising from 5 to 30 carbon atoms (ex cyclohexyl), ( v) a radical -CH 2 -C 6 H 10 -CH 2 -, (vi) a radical -CH 2 -C 6 H 4 -CH 2 -, (seen) a radical CF 3 , (wine) an atom of halogen; (ix) a hydroxy radical, (x) a carboxy radical, (xi) an alkoxy radical OR 'where R' has the same definition as that given
  • an aralkyl radical having an alkyl part containing between 5 and 14 carbon atoms and an aryl part containing between 6 and 12 carbon atoms, optionally substituted on the aryl part by halogens, alkyls and / or alkoxyls containing 1 to 3 carbon atoms,
  • species A1 include those of the following formulas
  • A2 species include those of the following formulas
  • the polyorganosiloxa ⁇ es A4 used comprise from 1 to 10 organofunctional groups per macromolecular chain
  • linear polyorganosiloxanes can be oils of dynamic viscosity at 25 ° C, of the order of 10 to 10,000 mPa.s at 25 ° C, generally of the order of 20 to 5,000 mPa.s at 25 ° C and , more preferably still, from 20 to 600 mPa s at 25 ° C, or gums having a molecular mass of the order of 1,000,000
  • cyclic polyorganosiloxanes When cyclic polyorganosiloxanes are involved, these consist of units (II) which can be, for example, of the dialkylsiloxy or alkylarylsiloxy type. These cyclic polyorganosiloxanes have a viscosity of the order of 1 to 5000 mPa s As examples of an organofunctional radical of the oxetane type linked to the backbone of the polyorganosiloxane A4, the group of formula below may be mentioned
  • the functional polyorganosiloxane oxetanes can be prepared by hydrosilylation of unsaturated oxetanes or condensation of oxetanes containing a hydroxy function.
  • X can represent an alkyl or cyclohexyl group; trifluoropropyl; perfiuoroalkyle; alkoxy or hydroxypropyl
  • R may represent an alkyl radical -C 10, cyclohexyl, trifluoropropyl or perfluoroalkyl in d to C 10 (0 ⁇ a ⁇ 1000); (1 ⁇ b ⁇ 1000):
  • this can in particular comprise at least one of the following organic species B1 ⁇ ⁇
  • alpha-olefin epoxides • alpha-olefin epoxides, NOVOLAC epoxides, epoxy soybean oil, epoxidized linseed oil, and epoxidized polybutadiene, _ ⁇ acrylates, and in particular
  • epoxidized acrylates preferably the oisomer of Bisphenol A- epoxydiacrylate (EBECRYL 600), • acryloglycero-polyester, preferably a mixture of trifunctional acrylate oligomer obtained from glycerol and polyester (EBECRYL 810),
  • multifunctional acrylates preferably pentaerythritol triacrylate (PETA), trimethylol propane triacrylate (TMPTA), 1, 6-hexanediol diacrylate (HDODA), trimethylolpropane ethoxylate triacrylate, thiodiethylene glycol diacrylate, tetraacrylethylene tetraethylene glycol, tetraethylethylene glycol diethylacrylate diacrylate diacrylate diacrylate diacrylate TRPGDA), thethylene glycol diacrylate (TREGDA), thmethylpropane trimethacrylate (TMPTMA),
  • alkenyl ethers linear or cyclic, and in particular:
  • vinyl ethers in particular dodecylvinylether (DDVE), cyclohexylvinylether (CVE), butanediol divinylether (BDVE), butanediol monovinylether (HBVE), cyclohexane dimethanol divinylether (CHDVE), cyclohexane dimethanol monovinyl) triethyleneglycol divinylether (DVE-3) and the vinyl ethers of formula:
  • Gt4 polyols, and preferably the compound of formula
  • the matrix B may also contain or be based on monomer (s), (co) ol ⁇ gomer (s) and / or (co) polymer (s), of polyorganosiloxane B2 nature, consisting of units of formula (IV) and terminated with units of formula (V) or cyclic units consisting of units of formula (IV) represented below
  • the polyorganosiloxanes B2 used comprise from 1 to 10 organofunctional groups (frB) per macromolecular chain
  • organofunctional groups frB
  • the linear polyorganosiloxanes B2 can be oils of dynamic viscosity at 25 ° C, of the order of 10 to 10,000 mPa s at 25 ° C, generally of the order of 20 to 5,000 mPa.s at 25 ° C and , more preferably still, from 20 to 600 mPa at 25 ° C. or gums having a molecular mass of the order of 1,000,000
  • cyclic polyorganosiloxanes B2 When cyclic polyorganosiloxanes B2 are concerned, these consist of units (IV) which can be, for example, of the dialkylsiloxy or alkylarylsiloxy type. These cyclic polyorganosiloxanes have a viscosity of the order of 1 to 5000 mPa s
  • organofunctional groups (frB) of the epoxy type linked to the polyorganosiloxane B2 backbone mention may be made of those of the following formulas:
  • organofunctional groups (frB) of the alkenylether type mention may be made of those contained in the following formulas:
  • n 0 or 1 and n "an integer between 1 and 5
  • CC 12 alkylene radical optionally substituted, - or a C 5 -C arylene radical
  • R 9 represents a linear or branched alkyl radical in CC 6 .
  • organofunctional dioxolane groups (frB)
  • organofunctional dioxolane groups (frB)
  • Polyorganosiloxanes B2 with epoxy, dioxolane or alkenylether (frB) functions are generally in the form of fluids having a viscosity at 25 ° C of 10 to 10,000 mm 2 / s and preferably from 20 to 600 mm 2 / s
  • the dynamic viscosity at 25 ° C of all the silicones considered in this description can be measured using a BROOKFIELD viscometer, according to AFNOR NFT 76 102 of February 1972
  • the alkenyl ether functional polyorganosiloxanes B2 can be prepared by hydrosilylation reaction between oils with Si-H units and vinyloxy functional compounds such as allylvinylether, allylvinyloxyethoxybenzene
  • the functional epoxy polyorganosiloxanes B2 can be prepared by hydrosilylation reaction between oils with Si-H units and epoxyfunctional compounds such as v ⁇ nyl-4 cyclohexeneoxide, allylglycidylether
  • the functional dioxolane B2 polyorganosiloxanes can be prepared by hydrosilylation of unsaturated dioxolanes.
  • the polyorganosiloxanes B2 which best meet the object of the invention are described in the formulas below and have at least one epoxy, alkenylether or oxetane group X can represent an alkyl, cyclohexyl, trifluoropropyl, perfiuoroalkyl, alkoxy or hydroxypropyl group.
  • R can represent a C 1 to C 10 alkyl, cyclohexyl, trifluoropropyl or C 1 to C 10 perfiuoroalkyl radical and (0 ⁇ a ⁇ 1000), (1 ⁇ b ⁇ 1000)
  • the initiation of the photopolymerization and / or crosslinking of the adhesive composition according to the invention is carried out thanks to the presence of at least one cationic and / or radical, and preferably cationic, photoinitiator C.
  • cationic photoinitiators can be chosen from onium borates
  • R10 represents a C6-C2O1 carbocyclic or heterocyclic aryl radical, said heterocyclic radical possibly containing nitrogen or sulfur as heteroelements
  • R 1 1 represents R 1 0 or a linear or branched alkyl or alkenyl radical in C- j -
  • radicals R 1 0 and R 11 being optionally substituted by a C-1-C25 alkoxy, C-1-C25 alkyl, nitro, chloro, bromo, cyano, carboxy, ester or mercapto group,
  • Ar 1 which may be identical or different from each other, each represent a monovalent phenyl or naphthyl radical, optionally substituted with one or more radicals chosen from a linear or branched C- alkyl radical
  • Ar2 which may be identical or different from each other or with Ar each represent a monovalent phenyl or naphthyl radical, optionally substituted with one or more radicals chosen from a linear or branched C-1-C-12 alkyl radical. preferably at C-
  • Ar3 which may be identical or different from each other, each represent a divalent phenylene or naphthylene radical, optionally substituted with one or more radicals chosen from a linear or branched C-
  • Y is then a divalent radical having the meanings Y 2 to Y ⁇ below • Y ⁇ a group of formula
  • Y 4 • a divalent residue chosen from S - • ,. - C - 'oo a linear or branched alkylene residue in C-
  • L 1 represents 1 gand hey to the metal M by ⁇ electrons, ligand chosen from the ligands ⁇ ⁇ -alkyl, ⁇ 5- cyclopendadiènyl and ⁇ ⁇ -cycloheptratnènyl and the ⁇ 6-aromatic compounds chosen from ligands ⁇ ⁇ -benzene optionally substituted and compounds having from 2 to 4 condensed cycles, each cycle being capable of contributing to the valence layer of the metal M by 3 to 8 ⁇ electrons,
  • L 2 represents a gand linked to the metal M by ⁇ electrons, a gand chosen from the hgands ⁇ 7 -cycloheptatr ⁇ ènyl and the compounds chosen from the optionally substituted ⁇ 6-benzene gands and the compounds having 2 with 4 condensed cycles, each cycle being capable of contributing to the valence layer of the metal M by 6 or 7 ⁇ electrons
  • • L3 represents from 0 to 3 identical or different hgands linked to the metal M by ⁇ , hgand (s) electrons cho ⁇ s ⁇ (s) among CO and N ⁇ 2 + , the total electronic charge q of the complex to which L 1 , L 2 and L 3 contribute and the ionic charge of the metal M being positive and equal to 1 or 2
  • R 12 which are identical or different, represent a phenyl radical substituted by at least one electron-withdrawing group such as, for example, OCF3, CF3, NO2, CN, and / or by at least 2 halogen atoms (especially fluorine), and this when the cationic entity is an onium of an element from groups 15 to 17, a phenyl radical substituted by at least one element or an electron-withdrawing group, in particular halogen atom (fluorine in particular), CF3, OCF3, NO2, CN, and this when the cationic entity is an organometallic complex of an element from groups 4 to 10,> an aryl radical containing at least two aromatic rings such as for example biphenyl, naphthyl, optionally substituted by at least one element or one electron-withdrawing group, in particular a halogen atom (especially fluorine), OCF3, CF3, NO2, CN, whatever the cationic entity
  • the results obtained are particularly advantageous with photoinitiators whose cationic entity is chosen from onium salts of formula (VI).
  • This family of cationic entities is described in numerous documents, in particular in patents US-A-4,026,705, US-A-4,032,673, US-A-4,069,056, US-A-4,136,102, US -A-4 173 476 More particularly, the borate anionic entity (VI) is chosen from the anions of formula [BX " a R 12 t,] " in which
  • R 12 identical or different, represent a phenyl radical substituted by at least one electro-attracting group chosen from OCF3, CF3, NO2 and CN, and / or by at least two fluorine atoms
  • the species which are particularly suitable for the anionic borate entity are the following [B (C 6 F 5 ) 4] - 5 "[B (C 6 H 3 (CF 3 ) 2) 4] -
  • the other cationic entities (2), (3) and (4) are also suitable in the context of the adhesives according to the invention.
  • these other cationic entities preferably used, a distinction is made - the oxoisothiochromanium salts of formula (VII), - the oxoisothiochromanium salts of formula (VII),
  • R 13 has the meaning given in this application WO in connection with the symbol R 1
  • a cationic entity of this type which is more preferred is that where R 1 represents an alkyl radical, linear or branched, in C1-C20
  • R 1 represents an alkyl radical, linear or branched, in C1-C20
  • salts oxoisothiochromanium which are particularly suitable, there may be mentioned in particular the sulfonium salt of 2-ethyl-4-oxo ⁇ soth ⁇ ochroman ⁇ um or 2-dodecyl-4-oxoisothiochromanium
  • the cationic polysulfonium entity preferably comprises a species or a mixture of species of formula (VIII 1) in which - the radicals Ar 1 , which are identical or different between them, each represent a phenyl radical, optionally substituted by a linear or branched C-
  • radicals Ar 2 identical or different from each other and with Ar1, each represent a phenyl radical, optionally substituted by a linear or branched C1-C4 alkyl radical,
  • the Ar 3 radicals each represent an unsubstituted para-phenylene radical
  • the mono-sulfonium species, when there are any, which fall within the framework of this preferential modality are the species of formula (IX) in which the symbols Ar 1 and Ar 2 have the preferred meanings indicated above in the preceding paragraph, including, when these radicals are directly linked together by a residue Y ', the installation of a valential bond or of the remainder - O -
  • cationic sulfonium entities there may be mentioned in particular
  • the borate anionic entity of formula [BX " a R> 12 ⁇ _] ⁇ is preferably chosen from the following anions 1 ', 2', 3 ', 4', 5 ', 6', 7 '
  • the polysulfonium borates, which will be used very preferably, are the salts formed by the association of the following cations and anions
  • polysulfonium borates can be prepared by exchange reaction between a salt of the cationic entity (halide such as for example chloride, lodide) with an alkali metal salt (sodium, lithium, potassium) of the anionic entity
  • a salt of the cationic entity halide such as for example chloride, lodide
  • an alkali metal salt sodium, lithium, potassium
  • the mono-sulfonium species (VIII 2) mentioned above may be in particular the co-products which are formed during the preparation of the polysulfonium cations and the presence of which can be more or less avoided
  • organometallic salts more readily used in practice are in particular ( ⁇ 5 - cyclopentadienyl) ( ⁇ 6 - toluene) Fe + - bis ( ⁇ 6 - benzene) Cr + le ( ⁇ 5 - cyclopentadienyl) ( ⁇ 6 - cumene) Fe + - bis ( ⁇ 6 - mesitylene) Fe + - and ( ⁇ 5 - cyclopentadienyl) ( ⁇ 6 - methyl-1-naphthalene) Fe +
  • onium borates (1) and (2) and the borates of organometal salts (4), selected as photoinitiator in the context of the invention mention may be made of the entire content of the patent applications EP 0 562 897 and EP 0 562 922 This content is fully incorporated by reference to the description
  • onium salt usable as photoinitiator C mention may be made of those disclosed in American patents US 4,138,255 and US 4,310,469 (CRIVELLO)
  • radical photoinitiators these ⁇ are based on benzophenones.
  • Radical photoinitiators can contain one or more phosphorus atoms, like those sold by Ciba-Geigy (Irgacure 1700) or BASF (Luci ⁇ n TPO)
  • the photoinitiator C in particular of cationic nature, is used in solution in an organic solvent (accelerator), preferably chosen from the proton donors and, more preferably still, from the following groups isopropyl alcohols, benzyl alcohols, diacetone alcohol , butyl lactate and mixtures thereof.
  • organic solvent preferably chosen from the proton donors and, more preferably still, from the following groups isopropyl alcohols, benzyl alcohols, diacetone alcohol , butyl lactate and mixtures thereof.
  • the photoinitiator C can also be used directly by solubilization in the matrix A and / or B
  • the adhesive according to the invention can also comprise at least one photosensitizer D
  • the use of a photosensitizer D is very profitable.
  • photosensitizer D can be selected from (poly) aromatic products - possibly metallic - and heterocychic products and, preferably, chosen from the following list of products phenothiazine, tetracene, perylene, anthracene, d ⁇ phenyl-9-10-anthracene thioxanthone, 2-chloroth ⁇ oxanthen-9-one, 1-chloro 4 propoxy 9H-th ⁇ oxanthen-9- one, ⁇ sopropyl-OH-th ⁇ oxanten-9-one, mixture of isomers 2 and 4, 2- ⁇ sopropyl-9H -thioxanthen- 9-one, benzophenone, [4- (4-methylphenylth ⁇ o) phenyl] phenylmethanone, 4-benzyl -4'- methyldiphenylsulphide, acetophenone, xanthone, fluorenone, anthraquinone, 9,10- dimethylanthrac
  • the adhesives according to the invention may contain a stabilization additive based on secondary or primary tertiary ahphatic amine, and preferably chosen from the derivatives described in patent application WO98 / 07798.
  • the invention also relates to an adhesive based on a polymerizable and or crosslinkable composition, under irradiation and / or under electron beam (s), cationically and / or free-radical, to assemble two plastic surfaces vis-à-vis screw, including
  • Polypropylene sheets are secured by UV application of a layer of adhesive comprising the formulation of an oxetane monomer Example 1
  • a control formulation respectively comprises by mass
  • Rhodorsil ® Photoinitiator 2074 from the company Rhodia sihcones
  • the adhesive formulated according to the invention comprises respectively by mass
  • Cyracure® 6105 from the company Union-Carbide stabilized with 10 ppm of Tinuvin 765, - 11.65% of Cyracure® TON201 from the company Union-Carbide,
  • Rhodorsil ® Photoinitiator 2074 from the company Rhodia sihcones
  • the adhesive formulated according to the invention comprises respectively by mass
  • UVACURE® 1534 resin from the company UCB stabilizes with 10 ppm of Tinuvin 765
  • Rhodorsil ® Photoinitiator 2074 from the company Rhodia Silicones
  • Each formulation is applied at different grammages on bluish or transparent rough polypropylene plates.
  • the plates are 500 ⁇ m thick and are laid horizontally.
  • Each plate comprising the adhesive is assembled with an adhesive-free plate by simple pressure
  • Example C 60 Transparent 100 0.2
  • Example 2A 60 Blue 100 '0 22
  • Example 2B 60 Blue 50 0 35
  • Example 3A 60 Blue 100 0 3

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
EP00981418A 1999-11-19 2000-11-16 Durch bestrahlung härtbare klebstoffzusammensetzung für kunstoff Withdrawn EP1237982A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9914577 1999-11-19
FR9914577A FR2801315A1 (fr) 1999-11-19 1999-11-19 Colle de plastique polymerisable et/ou reticulable sous irradiation a base de matrice a fonctions reactives
PCT/FR2000/003186 WO2001036512A1 (fr) 1999-11-19 2000-11-16 Colle pour plastique polymerisable et/ou reticulable sous irradiation a base de matrice a fonctions reactives

Publications (1)

Publication Number Publication Date
EP1237982A1 true EP1237982A1 (de) 2002-09-11

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EP (1) EP1237982A1 (de)
AU (1) AU1867301A (de)
FR (1) FR2801315A1 (de)
WO (1) WO2001036512A1 (de)

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FR2824838A1 (fr) * 2001-05-16 2002-11-22 Rhodia Chimie Sa Compositions silicones adhesives sensibles a la pression, leur procede de preparations et leurs utilisations
FR2825368A1 (fr) * 2001-05-30 2002-12-06 Rhodia Chimie Sa Compositions silicones adhesives sensibles a la pression, leur procede de preparations et leurs utilisations
FR2827870A1 (fr) * 2001-07-25 2003-01-31 Rhodia Chimie Sa Compositions silicones adhesives sensibles a la pression, leur procede de preparations et leurs utilisations
FR3095443B1 (fr) * 2019-04-26 2021-03-19 Arkema France Compositions réticulables ayant une faible viscosité pour revêtements et matériaux à haut indice de réfraction et à température de déflexion thermique élevée
CN118638511B (zh) * 2024-08-15 2024-12-17 博益鑫成高分子材料股份有限公司 一种保护膜用高粘性胶黏剂及其制作工艺

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AU1867301A (en) 2001-05-30
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