WO2001030930A1 - Anti-adherent silicone/adhesive complex with stabilising additive in silicone - Google Patents
Anti-adherent silicone/adhesive complex with stabilising additive in silicone Download PDFInfo
- Publication number
- WO2001030930A1 WO2001030930A1 PCT/FR2000/003015 FR0003015W WO0130930A1 WO 2001030930 A1 WO2001030930 A1 WO 2001030930A1 FR 0003015 W FR0003015 W FR 0003015W WO 0130930 A1 WO0130930 A1 WO 0130930A1
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- WO
- WIPO (PCT)
- Prior art keywords
- silicone
- adhesive
- complex according
- acrylate
- radical
- Prior art date
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- 0 C[C@@](*C[C@]1[C@@](C)CCCC1)[C@@]1[C@@](C2)[C@]2CCCC1 Chemical compound C[C@@](*C[C@]1[C@@](C)CCCC1)[C@@]1[C@@](C2)[C@]2CCCC1 0.000 description 7
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/55—Boron-containing compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
-
- 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
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/40—Adhesives in the form of films or foils characterised by release liners
-
- 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
- C09J2483/00—Presence of polysiloxane
- C09J2483/005—Presence of polysiloxane in the release coating
Definitions
- the present invention relates generally to so-called sticker complexes composed of a silicone / adhesive matrix.
- This type of complex is more particularly intended for a use in which the crosslinked or polymerized silicone matrix is affixed at the level of a support so as to make it non-stick with respect to the adhesive.
- Adhesive protective papers such as labels, decorative papers, adhesive tapes are in particular produced from this type of adhesive / silicone complex.
- the silicone oils or resins proposed for obtaining this type of coating with non-stick properties generally derive from cationic photocrosslinkable systems. They are more particularly monomers, oligomers and / or polymers of polyorganosiloxane nature and comprising reactive functional radicals capable of forming intra- and inter-catenary bridges, so as to obtain the non-stick coating. These reactive functional radicals are for example of the epoxy, oxetane, dioxolane and / or alkenyl ether type. These systems lead, after polymerization under UV or electron beam and in the presence of a polymerization initiator, to non-stick coatings which form so-called self-adhesive complexes with adhesives, applied online or after siliconization. When using the complex systems thus formed, the adhesive substrate can be easily dissociated from the silicone matrix by simple detachment and then fixed on any material by simple pressure.
- this detachment force can be stabilized, in particular during prolonged storage of the complexes on reels after their manufacture. Indeed, since these coils can sometimes reach more than a meter in diameter, very strong pressure is then exerted on the adhesives. Under the effect of this pressure, the adhesive can then interact with the silicone and cause detachment difficulties, incompatible with the end use of these complexes, for example as self-adhesive labels that are easily peelable.
- This problem of prolonged stability over time of the detachment forces arises particularly in the so-called in-line processes mentioned above and in which the adhesives are deposited in aqueous phase on the silicone, immediately after crosslinking of the silicone, for example by irradiation under UV or electron beam.
- the object of the invention is precisely to provide crosslinkable non-stick silicone systems whose release force remains stabilized during the aging of the complexes.
- the present invention aims in particular to propose a silicone / adhesive complex whose release force of the silicone / adhesive interface can be stabilized in particular to a value lower than 59.05 g / cm appreciated for a peeling speed of the order of 30 cm / min.
- the present invention relates to a silicone / non-stick adhesive complex
- a silicone coating which is derived from a monomer, oligomer or polyorganosiloxane polymer with epoxy and / or alkenyl ether and / or oxetane and / or dioxolane functional group (s) comprises, as an additive intended to stabilize over time the release force of a silicone / adhesive interface , a compound chosen from: - the borates of general formula (I):
- X represents an element of group 1A or 2A of the periodic table, • x represents an integer equal to 1 or 2,
- the two supports are made of two separate materials, arranged so that the silicone coating of the first support is in contact with the adhesive coating of the second support.
- This embodiment is in particular illustrated by systems known as self-adhesive labels. In this particular case, the release force of the silicone / adhesive interface is exerted during the separation of the two supports.
- the two supports are constituted respectively by each of the two faces of the same material.
- This second embodiment is in particular illustrated by the systems known as adhesive tapes.
- the non-stick coating that is to say based on the silicone matrix and the adhesive coating are brought into contact during the winding of the support on itself.
- the release force is exerted at the silicone / adhesive interface under the effect of the separation of a lower face with an upper face of the material.
- the action of the additive results in the complex claimed by a prolonged stabilization over time of the release force of a silicone / adhesive interface. This peeling force is maintained at an amplitude compatible with a subsequent peeling of the adhesive coating from the silicone coating, for example during the final use of these complexes as easily peelable adhesive labels or even as adhesive tapes.
- a detachment force is considered to be stabilized if, compared to its original amplitude, it does not change more than a factor of 8, preferably 5 and more preferably 3, after an aging test called FINAT 10, representative of an aging of 3 to 6 months at 20 ° C under pressure conditions of 70g / cm 2 .
- the initial detachment force that is to say evaluated according to the so-called FINAT 3 test representative of an aging of 20 hours at 20 ° C. and under pressure conditions of approximately 70 g / cm 2 , and which is exerted at the silicone / adhesive interface, is less than 31.49 g / cm and more preferably 23.62 g / cm.
- the additive used according to the invention preferably has at least one element from group 1A or 2A of the periodic table capable of acting with the ends of carboxylic or carboxylate chains of silicone.
- These elements from group 1A or 2A are preferably chosen from potassium, calcium, lithium and cesium.
- additives according to the invention are the borates of general formula (I), in which R ′ represents:
- a phenyl radical substituted by at least one element or an electron-withdrawing group in particular a halogen atom (especially fluorine) or CF 3 , OCF 3 , NO 2 , CN, and / or
- the species of the anionic borate entity which are very particularly suitable are the following: l ': [B (F 5 ) 4 ] - 4': [B (C 6 F 4 (OCF 3 )) 4 ]
- KB (C 6 F 5 ) 4 KB [C 6 H 3 (CF 3 ) 2 ] 4 , LiB [C 6 H 4 (OCF 3 )] 4 , KB [ C 6 H 4 (OCF 3 )] 4 , Na B [C 6 H 4 (OCF 3 )] 4 , CsB [C 6 H 4 (OCF 3 )] 4 , LiB [C 6 H 3 (OCF 3 ) 2 ] 4 , NaB [C 6 H 3 (CF 3 ) 2 ] 4 , CsB [C 6 H 3 (CF 3 ) 2 ] 4 , LiB (C 6 F 5 ) 4 , KB (C 6 F 5 ) 4 , NaB ( C 6 F 5 ) 4 , Ca [B (C 6 F 5 ) 4 ] 2 , Cs [B (C 6 F 5 )] 4 .
- This additive is present in an amount of 0.001 to 5% and preferably of
- silicone coating it derives from the crosslinking and / or polymerization of monomer (s), oligomer (s) or polymer (s) of organopolysiloxane nature carrying functional group (s) such ( s) as epoxy and / or alkenylether and / or oxetane and / or dioxolane.
- it is at least one monomer, oligomer or silicone polymer epoxy and or alkenylether and / or oxetane and / or crosslinkable and or polymerizable oxolane, liquid at room temperature or hot-melt at temperature below 100 ° C, and comprising: • at least one motif of formula:
- - R ° represents an alkyl, cycloalkyl, aryl, vinyl, hydrogen, alkoxy radical, preferably a lower alkyl in - Z, identical or different, is an organic substituent comprising at least one reactive epoxy, and / or alkenylether and / or oxetane and / or dioxolane and / or carbonate function. • and at least two silicon atoms.
- the corresponding silicones can be in linear or cyclic form.
- the reactive functions Z can be very varied. They can in particular be chosen from the following radicals:
- n ' represents 0 or 1 and n "an integer between 1 and 5
- CC 12 alkylene radical optionally substituted, - or a C 5 -C 12 arylene radical, preferably phenylene, optionally substituted, preferably by one to three C 1 -C 6 alkyl groups,
- R 4 represents a linear or branched C r C 6 alkyl radical.
- the polyorganosiloxanes used comprise from 1 to 10 organofunctional groups per macromolecular chain.
- an epoxyfunctional group this corresponds to epoxide levels varying from 20 to
- the 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, of
- cyclic polyorganosiloxanes When cyclic polyorganosiloxanes are involved, these consist of units 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.
- the epoxy or vinyloxyfunctional polyorganosiloxanes are generally in the form of fluids having a viscosity at 25 ° C of 10 to 10,000 mm 2 / s and preferably from 100 to 600 mm 2 / s.
- the dynamic viscosity at 25 ° C. of all the silicones considered in the present description can be measured using a BROOKFIELD viscometer, according to the AFNOR NFT 76 102 standard of February 1972.
- the vinyloxyfunctional polyorganosiloxanes can be prepared by hydrosilylation reaction between oils with Si-H units and vinyloxyfunctional compounds such as allylvinylether, aHyl-vinyl oxyethoxybenzene ...
- the functional epoxy polyorganosiloxanes can be prepared by hydrosilylation reaction between oils with Si-H units and epoxyfunctional compounds such as vinyl-4 cyclohexeneoxide, allylglycidylether ...
- the functional oxetane polyorganosiloxanes can be prepared by hydrosilylation of unsaturated oxetanes or condensation of oxetanes containing a hydroxy function.
- the functional dioxolane polyorganosiloxanes can be prepared by hydrosilylation of unsaturated dioxolanes.
- the silicones which best meet the object of the invention are described below and have at least one epoxide, alkenylether or oxetane group.
- X can represent an alkyl group; cyclohexyl; trifluoropropyl; perfluoroalkyl; alkoxy or hydroxypropyl, R a C 10 to C 10 alkyl radical, cyclohexyl, trifluoropropyl or C 10 to C 10 perfluoroalkyl and (0 ⁇ a ⁇ 1000); (1 ⁇ b ⁇ 1000)
- the additive is incorporated into the polymerizable and / or crosslinkable composition in the proportions mentioned above, before activation of the crosslinking and / or polymerization.
- the adhesive coating it can be very diverse in nature insofar as it is chemically compatible with the silicone coating.
- PSA pressure-sensitive adhesive emulsions
- alkyl acrylate monomers which are generally present in an amount of 50 to about 99% and preferably in an amount of 80 to 99% by weight and of polar copolymerizable monomers such as for example acrylic acid, in proportions more reduced.
- the monomers used to prepare the PSAs are selected according to their glass transition temperature, Tg, to give the polymers incorporating them the expected behavior in terms of adhesion and viscoelasticity.
- Tg glass transition temperature
- the monomers advantageously have a sufficiently low glass transition temperature, generally between -70 and -10 ° C and preferably is less than -30 C.
- these monomers are chosen from the group consisting of - (meth) acrylic esters such as the esters of acrylic acid and of methacrylic acid with hydrogenated or fluorinated CC 2 alkanols, preferably Cj-Cs, in particular l acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, tert-butyl acrylate, l acrylate, heptyl acrylate, octyl acrylate, iso-octyl acrylate, decyl acrylate, dodecyl acrylate, methyl methacrylate, methacrylate ethyl, n-butyl methacrylate, isobutyl methacrylate; vinyl nitriles including more particularly those having 3 to 12 carbon atoms, such as in particular acrylonitrile and methacrylon
- the monomers used in the emulsion polymerization are mainly alkyl (meth) acrylate monomers, present in an amount of 50% to about 99% and preferably in an amount of 80% to 99% by weight. relative to the weight of monomers present in the emulsion.
- alkyl acrylate monomers preferably have 4 to about 8 carbon atoms in the alkyl chain because they correspond to the best compromise in terms of hardness and adhesion.
- 2-ethylhexyl acrylate is chosen from 2-ethylhexyl acrylate, butyl acrylate, hexyl acrylate, heptyl acrylate, octyl acrylate, iso-octyl acrylate , decyl acrylate, isobutyl acrylate, dodecyl acrylate or mixtures thereof, methacrylates such as n-butyl methacrylate, methacrylic acid, acrylic acid, itaconic acid, maleic acid and / or acrylamide.
- the 2-ethylhexyl acrylate and its mixtures are more particularly suitable for the invention.
- the PSAs are generally prepared by emulsion polymerization by the radical route at atmospheric pressure and at a temperature generally between 10 and 90 ° C., of the corresponding monomers.
- this polymerization technique requires, in addition to the radical initiator, a mixture of anionic and / or nonionic emulsifiers to stabilize said emulsion and, where appropriate, of a transfer agent, with a concentration of monomers of between approximately 20 and 75% by weight of the emulsion.
- the monomers can be introduced in the form of a preemulsion into the reaction medium.
- any type of free radical initiator or initiator customary in emulsion polymerization may be suitable.
- initiators include hydroperoxides such as hydrogen peroxide, diisopropylbenzene hydroperoxide, sodium, potassium or ammonium persulfates, and cationic initiators such as azobis (isobutyronitrile) 4-4'azobis (4-cyano valeric acid).
- the amount of initiator (s) is generally between 0.05 and 2% by weight relative to the amount of the monomers.
- a second additive useful for stabilizing the release force of a silicone / adhesive interface This adhesive must of course be chosen so as to be soluble in the emulsion from which the adhesive coating is derived. Subject to this condition, it may be the same or different from that used in the silicone coating.
- the salts of group 1A or 2A and preferably potassium or calcium of the following compounds: - the carboxylates of formula OCOR " ⁇ , with R" representing a linear, branched or cyclic, saturated alkyl radical , unsaturated or aromatic, C 1 to C 12 and optionally substituted for example by one or more halogen atoms, (as examples of carboxylates, mention may be made of (C 2 H 5 ) (C 4 H 9 ) CHCOOK, ( CH 3 ) (CH 2 ) 7 CH CH (CH 2 ) 7 COOK, (CH 3 COO) 2 Ca, CH 3 -COOK,
- - fluorosulfonates such as potassium trifluoromethanesulfonate
- - esters or salts of phosphoric acid such as K 3 P0 4 , K 4 P 2 0 7 ,
- this second additive As a representative of this second additive, mention may in particular be made of potassium or calcium carbonate and bicarbonate, potassium hydrogen phthalate, potassium dimethylphosphonoacetate, potassium hydrogen tartrate, potassium oxalate, potassium hydrogen phosphate , potassium acetate and potassium trifluoromethanesulfonate.
- the additive can be introduced into the adhesive, and preferably into the PSA emulsion, up to 5% by weight. Its quantity can thus vary between 0.001% and 5% and preferably between 0.01% and 1% by weight.
- the complexes according to the invention can also comprise one or more additives chosen as a function of the intended final application.
- the additives can in particular be compounds optionally in the form of polymers, with mobile hydrogens such as alcohols, glycols and polyols, useful for improving the flexibility in particular of the silicone matrix after polymerization and / or crosslinking; mention may be made, for example, of polycaprolactones-polyols, in particular the polymer obtained from 2-ethyl-2- (hydroxymethyl) -1, 3-propane-diol and 2-oxepanone such as the product TONE POLYOL-301 sold by the company UNION CARBIDE, or the other commercial polymers TONE POLYOL 201 and TONE POLYOL 12703 from the company UNION CARBIDE.
- mobile hydrogens such as alcohols, glycols and polyols
- fatty esters of unsaturated acids epoxidized or not for example epoxidized soybean oil or epoxidized linseed oil, epoxidized 2-ethylhexylester, 2- ethylhexyl epoxy stearate, octyl epoxystea
- fillers such as in particular ground synthetic fibers (polymers) or natural fibers, calcium carbonate, talc, clay, dioxide titanium, precipitation or combustion silica; soluble dyes; oxidation and corrosion inhibitors; organosilicon adhesion modulators or not; agents fungicides, bactericides, antimicrobials; and / or any other material which does not interfere with the activity of the additive according to the invention.
- the silicone coating it can also be combined with a stabilization additive.
- It is generally an amino agent comprising at least one amine, the boiling point of which is greater than 150 ° C. and preferably greater than 200 ° C.
- This amine can be a secondary amine or a tertiary amine.
- HALS hindered amines used as a light stability agent
- hindered amines available in the industry have given good results, and in particular: the TINUVIN products marketed by the company CIBA GEIGY, in particular the TINUVIN 144 and TINUVIN 765 products, described below, the CYAGARD products marketed by CYTEC, in particular the product CYAGARD UV 1164L, and the products SANDUVAR, in particular the product SANDUVAR 3055, described below marketed by the company SANDOZ.
- the percentage of amino agent generally used by weight relative to the total weight of the silicone matrix is between 1 and 1,000 ppm and preferably between 10 and 100 ppm. In the case of an amino agent of the HALS type, the amount is of the order of 20 to 100 ppm.
- the complexes according to the invention may also contain other ingredients such as pigments, photosensitizers of fungicidal, bactericidal and antimicrobial agents, corrosion inhibitors, etc.
- the quantities of coating deposited on the supports are variable.
- the amounts of silicone coating generally range between 0.1 and 5 g / m 2 of treated surface. These amounts depend on the nature of the supports and on the desired non-stick properties. They are more often between 0.5 and 1.5 g / m 2 for non-porous substrates. As regards the quantities of adhesive coating, preferably they are less than 200g / m 2 and more preferably 100 g / m 2.
- the supports can be a metallic material such as tinplate, a cellulosic material of the paper or cardboard type for example, or a polymeric material of the vinyl type.
- Thermoplastic polymer films such as polyethylene, prolypropylene or polyester are particularly advantageous.
- this second material can be chosen from the materials offered for the first support and be of an identical nature or not to the first support.
- the support on which the silicone coating and / or the adhesive coating is applied may already be coated with an initial coating which is superimposed a coating according to the invention. It can thus be a sheet comprising a bitumen-type coating.
- the present invention also relates to articles (sheets, ribbons for example) comprising a complex according to the invention. They may in particular be labels, self-adhesive sheets or adhesive tapes.
- a second aspect of the present invention relates to the use of an additive as defined above for stabilizing the release forces of a silicone / adhesive complex as defined above by introducing said additive into said silicone coating.
- X represents an element from group 1A or 2A of the periodic table and preferably a potassium or calcium atom
- the groups R ′ which are identical or different, represent an aliphatic, linear, branched or cyclic, saturated, unsaturated or aromatic C, to C 12 radical preferably substituted by at least one element or an electron-withdrawing group, in particular a halogen atom, preferably fluorine with at least one of the radicals being mono-, poly- or perfluorinated and
- compositions which are described in the following examples, based on structural silicones:
- silicones are photopolymerized, after application, on polypropylene film of 50g / m 2 or on any paper support which, for example, is not very resistant to heat in ovens (certain coated papers).
- a coating head composed of five rollers, a weight of deposited silicone which is between 0.5 and 1 g / m 2 on plastic and 1 to 2 g / m2 on paper.
- the applied product is then exposed under ultraviolet irradiation at a running speed which varies between 50 and 1000 m / min, preferably greater than 100 m / min and in the presence of mercury vapor lamps sold by the company Fusion, power 120 W / cm or 240 W / cm and called H + , by preference to the nature of the irradiation, which is mainly emitted between 200 and 300 m.
- the number of lamps used depends on the width of the width. A lamp occupies a width of 20 cm.
- the number of lamps used depends on the speed of the process. A 120 W / cm lamp is enough to polymerize at 100 m / min. Two lamps will be effective for a process of 200 m / min or more.
- the coatings After exposure to ultraviolet light, the coatings are perfectly dry and an acrylic adhesive coating 50% in water is applied, the base polymer of which has the following composition:
- the adhesive is then heated to between 100 ° C and 150 ° C, preferably 100 ° C, for a time of less than 2 minutes so as to remove the water from the adhesive which is then transferred using a transfer cylinder on paper or plastic support.
- the detachment forces of the various complexes obtained are measured according to a standardized test (FINAT 10), that is to say under a force of 70g / cm 2 , with a peeling speed of 300 mm / min after storage for 20 h at 20 ° C, as well as after 7 days at 70 ° C, simulating an aging of 6 months at 20 ° C under pressure conditions of 70g / cm 2 .
- FINAT 10 a standardized test
- the release forces of the adhesive applied in-line are measured on a silicone deposited at a rate of 0.8 g / m 2 on a polyester film and then dried at a rate of 200 m / min, at 1 using two Fusion 120 W / cm (H + ) lamps.
- the silicone formulation is obtained by mixing 95 parts of polymer A with 2.5 parts of an 18% solution of the photoinitiator P ⁇ in isopropanol and five parts of polymer A 2 . The whole is shaken vigorously before use in the form of a coating bath on induction rollers.
- the adhesive used, applied to the photocrosslinked silicone is based on the polymer P., and is marketed under the name RHODOTAK 315P. It is applied as an emulsion at around 50% dry extract.
- the control test not comprising any additive in the adhesive is noted Additive 0.
- KB (C 6 F 5 ) 4 is added in variable quantity to the silicone before crosslinking.
- Examples 1-2 are repeated, but applying the adhesive used on the photocrosslinked silicone in the form of a tape. It is based on the polymer P 1 and is marketed under the name of TESA 4970. It is therefore in this case 100% dry extract.
- control test not comprising any adhesive is noted additive 0.
- the silicone formulation is obtained by mixing 95 parts of the polymer A1 with 2.5 parts of an 18% solution of the photoinitiator PU and 18% of the potassium salt KB (C 6 F 5 ) 4 in isopropanol and five parts of polymer A2.
- the adhesive used applied to the photocrosslinked silicone is based on the polymer P., and is marketed under the name RHODOTAK 315.
- the silicone is applied to a polyester at a rate of 0.8 g / m 2 and crosslinked at 100 m / min in the presence of an "Hg" electrode lamp sold by the company IST Gmbh.
- Example 6 an adhesive additivated with 0.5% potassium acetate is also used. The results obtained are presented in Table III below.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00974597A EP1242551A1 (en) | 1999-10-29 | 2000-10-27 | Anti-adherent silicone/adhesive complex with stabilising additive in silicone |
JP2001533916A JP2003513142A (en) | 1999-10-29 | 2000-10-27 | Anti-adhesive silicone / adhesive composite with stabilizing additives in silicone |
CA002389015A CA2389015A1 (en) | 1999-10-29 | 2000-10-27 | Anti-adherent silicone/adhesive complex with stabilising additive in silicone |
AU12839/01A AU1283901A (en) | 1999-10-29 | 2000-10-27 | Anti-adherent silicone/adhesive complex with stabilising additive in silicone |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR99/13622 | 1999-10-29 | ||
FR9913622A FR2800383B1 (en) | 1999-10-29 | 1999-10-29 | SILICONE COMPLEX / ADHESIVE ADHESIVE WITH STABILIZATION ADDITIVE IN SILICONE |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001030930A1 true WO2001030930A1 (en) | 2001-05-03 |
Family
ID=9551560
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2000/003015 WO2001030930A1 (en) | 1999-10-29 | 2000-10-27 | Anti-adherent silicone/adhesive complex with stabilising additive in silicone |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1242551A1 (en) |
JP (1) | JP2003513142A (en) |
AU (1) | AU1283901A (en) |
CA (1) | CA2389015A1 (en) |
FR (1) | FR2800383B1 (en) |
WO (1) | WO2001030930A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002096998A1 (en) * | 2001-06-01 | 2002-12-05 | Rhodia Chimie | Compositions based on radiation-curable functionalised silicones and anti-adhesive coatings obtained from same |
WO2004031167A1 (en) | 2002-10-01 | 2004-04-15 | Basf Aktiengesellschaft | Alkyl glycidol carbonates used as co-surfactants |
US6881765B2 (en) * | 2003-03-10 | 2005-04-19 | Toagosei Co., Ltd. | Curable release agent and separator using same |
US7067605B2 (en) * | 2002-04-08 | 2006-06-27 | Kaneka Corporation | Organic polymer having epoxy-and/or oxetanyl-containing silicon group at the end and process for producing the same |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0581540A1 (en) * | 1992-07-30 | 1994-02-02 | General Electric Company | Silicone release composition |
US5397813A (en) * | 1993-11-12 | 1995-03-14 | General Electric Company | Premium release UV curable epoxysilicone compositions |
FR2752582A1 (en) * | 1996-08-21 | 1998-02-27 | Rhone Poulenc Chimie | COMPOSITIONS BASED ON POLYORGANOSILOXANES WITH RETICULABLE FUNCTIONAL GROUPS AND THEIR USE FOR MAKING ANTI-ADHERENT COATINGS |
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1999
- 1999-10-29 FR FR9913622A patent/FR2800383B1/en not_active Expired - Fee Related
-
2000
- 2000-10-27 EP EP00974597A patent/EP1242551A1/en not_active Withdrawn
- 2000-10-27 CA CA002389015A patent/CA2389015A1/en not_active Abandoned
- 2000-10-27 AU AU12839/01A patent/AU1283901A/en not_active Abandoned
- 2000-10-27 WO PCT/FR2000/003015 patent/WO2001030930A1/en not_active Application Discontinuation
- 2000-10-27 JP JP2001533916A patent/JP2003513142A/en not_active Abandoned
Patent Citations (3)
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EP0581540A1 (en) * | 1992-07-30 | 1994-02-02 | General Electric Company | Silicone release composition |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2002096998A1 (en) * | 2001-06-01 | 2002-12-05 | Rhodia Chimie | Compositions based on radiation-curable functionalised silicones and anti-adhesive coatings obtained from same |
FR2825367A1 (en) * | 2001-06-01 | 2002-12-06 | Rhodia Chimie Sa | COMPOSITIONS BASED ON FUNCTIONALIZED SILICONES CURING UNDER IRRADIATION AND ANTI-ADHERENT COATINGS OBTAINED FROM THESE COMPOSITIONS |
US7109251B2 (en) | 2001-06-01 | 2006-09-19 | Rhodia Chimie | Compositions based on radiation-curable functionalized silicones and anti-adhesive coatings obtained from same |
US7067605B2 (en) * | 2002-04-08 | 2006-06-27 | Kaneka Corporation | Organic polymer having epoxy-and/or oxetanyl-containing silicon group at the end and process for producing the same |
WO2004031167A1 (en) | 2002-10-01 | 2004-04-15 | Basf Aktiengesellschaft | Alkyl glycidol carbonates used as co-surfactants |
US6881765B2 (en) * | 2003-03-10 | 2005-04-19 | Toagosei Co., Ltd. | Curable release agent and separator using same |
Also Published As
Publication number | Publication date |
---|---|
JP2003513142A (en) | 2003-04-08 |
AU1283901A (en) | 2001-05-08 |
EP1242551A1 (en) | 2002-09-25 |
FR2800383A1 (en) | 2001-05-04 |
FR2800383B1 (en) | 2002-01-18 |
CA2389015A1 (en) | 2001-05-03 |
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