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WO2000000566A1 - Composition adhesive thermofusible, adhesif collant a chaud et procede de collage a l'aide de la composition adhesive thermofusible - Google Patents

Composition adhesive thermofusible, adhesif collant a chaud et procede de collage a l'aide de la composition adhesive thermofusible Download PDF

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Publication number
WO2000000566A1
WO2000000566A1 PCT/US1999/013468 US9913468W WO0000566A1 WO 2000000566 A1 WO2000000566 A1 WO 2000000566A1 US 9913468 W US9913468 W US 9913468W WO 0000566 A1 WO0000566 A1 WO 0000566A1
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WO
WIPO (PCT)
Prior art keywords
composition
hot
heat
adhesive
adhesive composition
Prior art date
Application number
PCT/US1999/013468
Other languages
English (en)
Inventor
Kohichiro Kawate
Shigeyoshi Ishii
Mario A. Perez
Original Assignee
Minnesota Mining And Manufacturing Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Minnesota Mining And Manufacturing Company filed Critical Minnesota Mining And Manufacturing Company
Priority to US09/355,602 priority Critical patent/US6265460B1/en
Publication of WO2000000566A1 publication Critical patent/WO2000000566A1/fr

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    • H—ELECTRICITY
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    • H01L24/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
    • H01L24/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/04—Homopolymers or copolymers of ethene
    • C09J123/08—Copolymers of ethene
    • C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C09J123/0869—Acids or derivatives thereof
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    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
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    • H01L2924/07802—Adhesive characteristics other than chemical not being an ohmic electrical conductor
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/095—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00 with a principal constituent of the material being a combination of two or more materials provided in the groups H01L2924/013 - H01L2924/0715
    • H01L2924/097—Glass-ceramics, e.g. devitrified glass
    • H01L2924/09701—Low temperature co-fired ceramic [LTCC]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/14—Integrated circuits

Definitions

  • the present invention relates to a hot-melt adhesive composition, a heat-bonding film adhesive, and a bonding method using a hot-melt adhesive composition, which are suitable for adhering electronic parts or producing integrated circuit (IC) packages.
  • the adhesive composition of the present invention can be used as a reactive (thermosetting) thermal adhesion type adhesive.
  • So-called reactive (thermosetting) hot-melt adhesives which can be cured (crosslinked) after adhesion for improving properties such as heat resistance, are available as a kind of so-called hot-melt adhesives that can be used for thermal adhesion.
  • the following adhesives 1) through 6) are exemplified as conventional reactive hot-melt adhesives:
  • Moisture-curing hot-melt adhesives comprising polymers having an isocyanate group (see U.S. Patent No. 5,418,288 corresponding to JP-A-6-158017);
  • Thermosetting hot-melt adhesives comprising polymers having a glycidyl group and phenol resins (see JP-A-6172731); 5) Hot-melt adhesives that are crosslinked by irradiation after thermal adhesion
  • Crosslinkable resin compositions comprising a terpolymer of ethylene, an ⁇ , ⁇ -unsaturated carboxylic acid, and an ⁇ , ⁇ -unsaturated carboxylate ester; a copolymer of ethylene and glycidyl methacrylate; and a diallyl phthalate compound as a crosslinking agent (see JP-A-4-45123).
  • compositions can be used as adhesives that are curable with light-irradiation because the cationic polymerization catalyst, which has been activated with light-irradiation, greatly increases the reaction rate of the epoxy resin.
  • the other components are free radically polymerized polymers such as acrylic polymers that are disclosed in U.S. Patent No. 5,721,289; thermoplastic polyolefins that are disclosed in U.S. Patent No. 5,709,948; and the like.
  • the above compositions can be used as curable adhesives (U.S. Patent No. 5,721,289) and photocurable adhesives (U.S. Patent No. 4,401,537), that have good reactivity.
  • Hot-melt adhesives containing polyethylene copolymers as adhesive components are desirably used in the electrical field.
  • Such polyethylene type hot-melt adhesives are chemically stable, and their stability is proved by a test under severe conditions, for example, a pressure cooker test that is used to test semiconductor products.
  • conventional polyethylene type hot-melt adhesives are not designed to perform a crosslinking reaction (curing reaction) between molecules of polyethylene copolymers. Thus, they have low heat resistance and cannot exert a sufficient bonding force at a temperature higher than a bonding temperature as can be readily understood from the adhesion mechanism of hot-melt adhesives. Such low heat resistance particularly limits the application of hot-melt adhesives in the electrical field.
  • the tapes cannot be used in such conditions that the tapes are thermocompressed at a temperature of about 180°C and dipped in a solder bath, followed by maintaining them in a hot atmosphere of 230 to 260°C.
  • the above conventional reactive hot-melt adhesives 1) through 6) still have one or more of the following drawbacks a) through g): a) Some hot-melt adhesives have a low crosslinking rate and require a long post cure time (for example, the above adhesives 1) and 2)); b) A certain hot-melt adhesive requires moisture for the crosslinking reaction, and is less suitable for adhering parts that are hardly in contact with air (for example, the above adhesive 1)); c) A certain hot-melt adhesive generates water as a byproduct, which has adverse affects, such as deterioration of adhesion strength with time (for example, the above adhesive 2)); d) Some hot-melt adhesives require a solvent for forming them in the form of a film and the residual solvent may have adverse effects after the completion of adhering (for example, the above adhesives 1) to 4)); e) In some hot-melt adhesives, the crosslinking reaction gradually proceeds when they are stored even at room temperature (about 25°C) and, therefore, they
  • the above described epoxy resins are usually liquids at room temperature (around 25°C). Some epoxy resins are solids that can be liquefied by heating, but their flowability (for example, properties such as MFR, which will be explained later) under heated conditions is relatively large. Thus, an epoxy resin alone cannot be used as a hot-melt adhesive.
  • the high reactivity of epoxy resins makes it difficult to maintain both thermal curability and flowability while being heated of the compositions comprising the epoxy resins at high levels and to use the compositions as hot-melt adhesives.
  • the epoxy resins tend to be separated from other components when the compositions comprising the epoxy resins are press adhered at a high temperature as hot- melt adhesives. Also, there is the fear of outgassing. The separated epoxy resins may lead to excessive flowability, low adhesion force, contamination of adherents, pollution of environment, and the like. When the epoxy resins are separated, the elasticity of the compositions cannot be sufficiently increased after the compositions are thermally cured.
  • the above resin composition comprising an epoxy resin and a cationic polymerization catalyst does not contain a polyethylene copolymer as an essential component and, therefore, has less chemical stability than the above polyethylene-type hot melt adhesives.
  • the object of the present invention is to provide a hot-melt adhesive composition, which can help solve the problems a) through g) associated with the above conventional reactive hot-melt adhesive compositions, the problems associated with the above compositions comprising the epoxy resin when used as the hot-melt adhesives, and also the problems associated with the conventional polyethylene type hot melt adhesives at the same time.
  • thermosetting hot- melt adhesive composition comprising a polyethylene copolymer having epoxy groups in a molecule as an epoxy component.
  • the composition further comprises a cationic polymerization catalyst, a heat-bonding film adhesive comprising a hot coating film of the thermosetting hot-melt adhesive composition that has been activated by irradiation with UV rays, and an adhering method using the hot coating film.
  • the hot-melt adhesive composition (which may be simply referred to as "adhesive composition") is chemically stable since it contains a polyethylene copolymer as an essential component. In addition, this composition has good heat resistance since it cures through the intermolecular crosslinking reaction of the polyethylene copolymer having epoxy groups.
  • the hot-melt adhesive composition of the present invention does not contain a curing agent that is originally in the activated state.
  • the adhesive composition is stable against heat and can be formed into a film by hot-melt coating without gelation of the composition caused by heat. Therefore, a heat-bonding film adhesive and a hot-melt film can be continuously produced easily.
  • the obtained film can solve the above problem f), since it can be thermally cured at a temperature of 120°C or higher after being activated with the UV irradiation and, thus, it can be thermally cured without the necessity of radiation-crosslinking after adhesion like the conventional thermosetting heat-bonding film adhesive or hot-melt film.
  • the composition of the present invention may be used as a thermally curable hot-melt adhesive after irradiation of UV rays, since it contains a polyethylene copolymer having epoxy groups in a molecule as an epoxy component. That is, the polyethylene copolymer having epoxy groups in a molecule improves flowability and thermal curability of the composition in the hot-melt state after the irradiation of UV rays. In addition, problems associated with the separation of epoxy resins (excessive flowability, low adhesion force, etc.) and the problem of outgassing can be solved. Accordingly, it is preferable that the epoxy component contains substantially no epoxy resins, but essentially consists of a polyethylene copolymer having epoxy groups.
  • the hot-melt adhesive composition of the present invention is in the solid state at room temperature (about 25°C) prior to and after activation with UV rays, but can be thermocompressively adhered at a specific temperature under a relatively low pressure in a short time (for example, at a temperature between 100 and 200°C and under pressure between 0.1 and 40 kg/cm ⁇ for 0.1 to 30 seconds).
  • the adhesive composition can be cured (or crosslinked) by heating during the thermocompressive adhering or heating after the thermocompressive adhering (post-curing) in the absence of moisture.
  • the adhesive composition can be used as a heat-bonding thermosetting type adhesive.
  • the above described drawbacks which appear in the radiation-crosslinkable and moisture- curable (crosslinkable) hot-melt adhesives, can be overcome.
  • thermosetting reaction is substantially a reaction between the epoxy groups of an ethylene-glycidyl (meth)acrylate copolymer.
  • no reaction by-products such as water, generate.
  • Such a reaction can be effectively catalyzed by a cationic polymerization catalyst.
  • the adhesive composition of the present invention melts at a temperature of, for example, 120°C or higher, and can be easily hot-melt coated without gelation.
  • the composition has relatively high flowability in the hot-melt state and, thus, requires no solvent for coating or forming it into a film.
  • the adhesive composition after UV ray activation, may be thermally cured at a temperature lower than 120°C, or used as a room temperature-curable hot-melt adhesive, if it is not necessary to shorten the curing time, since the composition is gradually cured, even at room temperature (about 25°C).
  • the modulus of the adhesive composition which is usually expressed by a storage modulus G', after the completion of adhesion (that is, after the completion of the curing reaction) is usually at least 10 ⁇ dyne/cm 2 , preferably at least 10? dyne/cm 2 , at 280°C.
  • the modulus is less than 10 ⁇ dyne/cm 2 , solder reflow resistance deteriorates, so that the adhesive composition may not be suitable for the adhesion of electronic parts or the production of IC packages.
  • the modulus is too low, wire bonding may not be satisfactorily carried out.
  • the above modulus is defined as follows: A sample of the adhesive composition (e.g., a film adhesive, etc.) after UV ray irradiation is heated from 80°C to 280°C at a heating rate of 5°C/min. with a dynamic viscoelastometer. The above modulus is a value measured at 280°C at a shear rate of 6.28 rad/sec.
  • the adhesive composition of the present invention has very high thermal stability prior to UV ray activation. Thus, it can be processed in the form of a film by melt coating or extrusion molding at a relatively high temperature.
  • the curing reaction between molecules of the polyethylene copolymers is very mild at a heating temperature during such processing and, thus, the adhesive composition does not gel, or its viscosity (complex modulus) does not increase to a level at which continuous production becomes difficult.
  • storage stability of the adhesive composition can be improved, since the curing reaction does not substantially proceed at a temperature lower than 90°C prior to
  • the adhesive composition can be stored at a temperature of 30°C or less, and can be used as a thermosetting adhesive for about one month.
  • the adhesive composition of the present invention contains a thermoplastic polymer having no epoxy group in the molecules as an essential component in addition to the polyethylene copolymer having epoxy groups in a molecule. Therefore, adhesion properties of the adhesive composition after irradiation of UV rays can be easily increased.
  • thermoplastic polymers are preferably polyethylene copolymers having no epoxy group in the molecules, in particular, ethylene-alkyl acrylate copolymers, such as ethylene- ethyl acrylate copolymers.
  • polyethylene copolymers have high compatibility with polyethylene copolymers having an epoxy group in a molecule and can effectively improve the thermocompressive adhesion or melt-coating properties of the adhesive composition without deteriorating the adhesion properties.
  • the amount of the polyethylene copolymer having an epoxy group in a molecule is usually from 40 to 80 wt. %, preferably from 45 to 75 wt. % of the whole weight of the composition.
  • the amount of the thermoplastic polymer having no epoxy group in the molecules is usually from 15 to 55 wt. %, preferably from 24 to 50 wt. % of the whole weight of the composition.
  • the amount of the thermoplastic polymer is too low, the above effects may not be attained.
  • the amount of the thermoplastic polymer is too large, the reactivity (heat curability) tends to deteriorate.
  • the adhesive composition of the present invention may contain polymers other than the above two kinds of polyethylene copolymers insofar as the effects of the present invention are not impaired.
  • the adhesive composition can be usually prepared by mixing raw materials with a kneading or mixing apparatus until they are substantially uniformly mixed.
  • a kneading or mixing apparatus such as a kneader, a roll mill, an extruder, a planetary mixer, a homo-mixer, and the like.
  • a mixing temperature and time are selected so that reaction of the polyethylene copolymer does not substantially proceed.
  • the temperature is between 20 and
  • the polyethylene copolymer having epoxy groups in a molecule may be, for example, an ethylene-glycidyl (meth)acrylate copolymer.
  • the ethylene-glycidyl (meth)acrylate copolymer.
  • (meth)acrylate copolymer (hereinafter sometimes referred to as "copolymer (a)") is cured when the adhesive composition after UV ray activation is heated at a specific temperature and serves to increase cohesive force of the cured material.
  • Such a high cohesive force is advantageous for improving adhesion properties, such as peel strength, of the adhesive composition.
  • Copolymer (a) also serves to melt the precursor of the adhesive composition at a relatively low temperature and to facilitate melt coating of the composition. Furthermore, copolymer (a) provides the adhesive composition with good thermal adhesion properties, which means adhesion properties against an adherent after the composition is molten and in contact with the adherent, cooled, and solidified.
  • Copolymer (a) may be prepared by polymerizing a monomer mixture containing: i) a glycidyl (meth)acrylate monomer, and ii) an ethylene monomer.
  • copolymer (a) is:
  • Terpolymers of glycidyl (meth)acrylate, ethylene and an alkyl (meth)acrylate Such copolymers usually contain at least 50 wt. %, preferably at least 75 wt. % of repeating units formed by the polymerization of the monomer mixture of glycidyl (meth)acrylate and ethylene, based on the whole copolymer.
  • the weight ratio of the glycidyl (meth)acrylate (G) to ethylene (E) (G:E) in the above repeating units is usually between 50:50 and 1:90, preferably between 20:80 and 5:95.
  • the copolymers (a) may be used independently or as a mixture of two or more.
  • the flowability of the polyethylene copolymer having epoxy groups in a molecule and the thermoplastic polymer having no epoxy group in the molecules such as a polyethylene copolymer having no epoxy group, which are used in the composition of the present invention, while being heated can be determined in accordance with conditions for hot-melt coating (e.g., temperature, coating methods, etc.).
  • the melt flow rate (MFR) at 190°C of the polyethylene copolymer is usually in the range between 1 and 1,000 g/10 min., preferably in the range between 10 and 700 g/10 min., in particular in the range between 100 and 500 g/10 min.
  • MFR is a value measured according to JIS K 6760.
  • the weight average molecular weight of the polyethylene copolymer is so selected that MFR is in the above range.
  • MFR is too low, it may be difficult to continuously produce a heat-bonding film adhesive or a hot-melt film having a desired thickness.
  • MFR is too high, the composition flows excessively during the heat-bonding adhering operation and, thus, it flows out from the gap between the adherents, or the thickness of the adhesive layer becomes too small so that the adhesion performance tends to deteriorate.
  • the total amount of the polyethylene copolymer having epoxy groups in a molecule and the polyethylene copolymer having no epoxy group in the molecules is preferably between 50 and 99.9 wt. % of the whole adhesive composition.
  • the modulus of the adhesive composition after thermosetting tends to decrease.
  • the total amount of the polyethylene copolymers is too high, the reactivity tends to deteriorate.
  • the cationic polymerization catalyst is a compound that generates a cationic active species such as a Lewis acid upon irradiation with UV rays, and catalyzes the ring-opening reaction of the epoxy ring.
  • the cationic polymerization catalyst are organic metal complex salts comprising at least one ligand (e.g. cyclopentadienyl anion, indenyl anion, (xylene)hexafluoroantimonate anion, hexafluorophosphate anion, etc.) and a metal cation (e.g. cation of iron, chromium, molybdenum, tungsten, manganese, rhenium, ruthenium, osmium, etc.), boron fluoride complexes, and the like.
  • ligand e.g. cyclopentadienyl anion, indenyl anion, (xylene)hexafluoroantimonate anion, hexafluorophosphate anion, etc.
  • a metal cation e.g. cation of iron, chromium, molybdenum, tungsten, manganese, rhenium, ruthen
  • the amount of the cationic polymerization catalyst is usually between 0.01 and 10 wt. % of the whole adhesive composition.
  • the heat-bonding film adhesive is a thermosetting film-form adhesive consisting of the hot-melt coating film of the above adhesive composition, which has been activated by irradiation with UV rays.
  • the heat-bonding film adhesive is an advantageous application form for a thermal adhesion type adhesive and solves the problems of the above described conventional hot-melt adhesives.
  • the heat-bonding film adhesive can thermally bond a pair of adherents by placing the film between the adherents and heat pressing them at a specific temperature.
  • the film when the film is post-cured for a specific time, it displays good adhesion properties.
  • the curing reaction of the film proceeds at a temperature of 120°C or higher and the film can exhibit sufficient adhesion strength (for example, 1 to 15 kg/25 mm or higher) by heating for a period of from 1 minute to 24 hours (heating during the thermocompressive adhering or in the post-cure).
  • the curing reaction rate at 120°C is moderate, but a sufficient curing time (for example, at least 10 hours) can achieve the desired adhesion properties.
  • the film can be heated at a temperature in the range between 130 and 300°C.
  • the heat-bonding film adhesive may be prepared as follows:
  • an adhesive composition is melt-coated on a substrate to form a film-form precursor.
  • the film-form precursor is irradiated and activated with UV rays to obtain a heat- bonding film adhesive.
  • the dose of the UV rays is usually between 100 and 10,000 mJ/cm 2 (an integrated dose at 360 nm).
  • the above substrate may be a liner, or one of adherents that will be bonded.
  • the liner may be any conventional one, for example, a release paper, a release film, etc.
  • Melt coating is carried out at a temperature in the range between 60 and 150°C.
  • any conventional coating means such as a knife coater, a die coater, and the like may be used.
  • a film-form precursor may be produced by extrusion without using a substrate.
  • the heat-bonding film adhesive is finished with protecting one or both adhesive surfaces with a liner.
  • the film may be finished without a liner.
  • the thickness of the heat-bonding film adhesive is preferably between 0.001 and 5 mm, in particular between 0.005 and 0.5 mm.
  • the thickness is preferably between 0.001 and 5 mm, in particular between 0.005 and 0.5 mm.
  • the thickness is too low, the handling of the film may become difficult.
  • the thickness is too high, the effects become uneven in the thickness direction of the film, and thus the reliability of the film as a film adhesive may tend to decrease.
  • the heat-bonding film adhesive with the liners can be used as follows: First, the liners are removed from the film adhesive having the liners and sandwiched between the first and second adherents to form a laminate consisting of the first adherent, film adhesive, and second adherent, which are typically laminated in this order. Next, the laminate is heat-pressed at a temperature in the range between 80 and 300°C under pressure in the range between 0.1 and 100 kg/cm 2 to form a bonded structure in which the three elements are closely bonded. This method can bond the two adherents with a sufficient adhesion strength in a time period of between 0.1 and 30 seconds.
  • the heat-bonding film adhesive of the present invention can exhibit a sufficient adhesion strength only by the above heat pressing.
  • the film can be post-cured for the increase of the adhesion strength.
  • the bonded structure is post-cured usually at a temperature of at least 120°C, preferably between 130 and 300°C for a time period in the range between 1 minute and 24 hours.
  • preferable conditions include a temperature in the range between 140 and 200°C and a time period in the range between 30 minutes and 1.2 hours.
  • the adhesive composition of the present invention may contain various additives in addition to the above components, insofar as the effects of the present invention are not impaired.
  • additives are antioxidants, fillers, (e.g., inorganic fillers, conductive particles, etc.), lubricants such as waxes, rubber components, tackifiers, crosslinking agents, curing accelerators, colorants (e.g., pigments, dyes, etc.), and the like.
  • the adhesive composition and heat-bonding film adhesive according to the present invention are preferably used for adhering electronic parts, for example, adhering IC devices and printed circuit boards. Furthermore, they can be preferably used for adhering a
  • plastic articles such as polyamide, polyimide, polyetherimide, polycarbonate, polyethylene, polypropylene, polyester, and the like; and adhering a plastic article and an article made of other material (e.g., fibers, metals, semiconductive materials, such as silicon, ceramics, glasses, etc.).
  • metals are copper, iron, nickel, gold, silver, aluminum, tungsten, molybdenum, platinum, and the like.
  • the production of the adhesive composition of the present invention includes no polymerization step using monomers as starting materials.
  • the amount of unreacted monomers or volatile organic materials derived from the monomers can be decreased as much as possible. That is, it is possible to effectively suppress bubbling due to volatile materials that are generated during the solder reflow or monomer odors that are unpleasant to the users.
  • the adhesive composition of the present invention When used in the form of an adhesive layer stuck on a substrate such as a plastic film, a fabric, a metal foil, etc., it can be used as an adhesive tape that can be heat bonded. Furthermore, the adhesive composition of the present invention can be used as a sealant besides the adhesive.
  • An adhesive composition of this Example was prepared by mixing an ethylene- glycidyl methacrylate copolymer (BONDFAST CG 5001 available from Sumitomo
  • the adhesive composition of this Example was used as a sample, and its complex modulus ⁇ * (a measure for viscosity) was measured using a dynamic viscoelastometer
  • the mass of the adhesive composition of this Example was placed between a pair of polyethylene terephthalate (PET) films (release films) and passed through a knife gap heated at 140°C. A film-form precursor having a thickness of 0.1 mm was obtained.
  • PET polyethylene terephthalate
  • the film-form precursor was irradiated with UV rays using a high pressure mercury lamp of 20 W/cm from a distance of 20 cm.
  • a heat-bonding film adhesive was formed.
  • the UV rays were irradiated at two doses of 630 mJ/cm 2 and 1,540 mJ/cm 2 .
  • the storage moduli (G 1 ) of the film adhesive at various temperatures are shown in Table 1.
  • the storage modulus was measured at each temperature with the sample of the heat-bonding film adhesive after 25 minutes from the UV ray irradiation by heating the sample from 80°C to 280°C at a heating rate of 5°C/min. and measuring the modulus at a shear rate of 6.28 rad/sec.
  • the modulus of the heat-bonding film adhesive prior to the UV ray radiation (the precursor) is also shown in Table 1 (Reference Example).
  • the heat-bonding film adhesive was easily heat cured at a temperature of 120°C or higher, and its storage modulus at 280°C was 10 ⁇ dyne/cm 2 or higher at any dose.
  • a piece of the film adhesive (length of 30 mm, width of 10 mm and thickness of 0.1 mm) was inserted between a copper plate (length of 30 mm, width of 25 mm and thickness of 0.3 mm and a copper foil (length of 100 mm, width of 10 mm and thickness of 0.05 mm) with trueing up the edges of the film adhesive with those of the copper foil. Then, the laminate was thermally pressed at 180°C under pressure of 30 kg/cm 2 for 10 seconds.
  • An adhesive composition of this Example was prepared in the same manner as in Example 1, except the weight ratio of the ethylene-glycidyl methacrylate copolymer to ethylene-ethyl acrylate copolymer to cationic polymerization catalyst was changed to 50:49.5:0.5 and a heat-bonding film adhesive of this Example was prepared in the same manner as in Example 1 using the adhesive composition of this Example.
  • the dose of UV rays was 1,540 mJ/cm 2 .
  • An adhesive composition of this Example was prepared in the same manner as in Example 1 except that no ethylene-ethyl acrylate copolymer was used, and the weight ratio of the ethylene-glycidyl methacrylate copolymer to cationic polymerization catalyst was 99.5:0.5 and a heat-bonding film adhesive of this Example was prepared in the same manner as in Example 1 using the adhesive composition of this Example.
  • the dose of UV rays was 1,540 mJ/cm 2 .
  • Example 4 The composition of this Comparative Example had insufficient adhesion properties after the irradiation of UV rays for use as a heat-bonding film adhesive, although it had good heat resistance and chemical stability.
  • Example 4 The composition of this Comparative Example had insufficient adhesion properties after the irradiation of UV rays for use as a heat-bonding film adhesive, although it had good heat resistance and chemical stability.
  • An adhesive composition of this Example was prepared in the same manner as in Example 1, except that cyclopentadienyliron(II) (xylene)hexafluoroantimonate was used as a cationic polymerization catalyst, and then a heat-bonding film adhesive of this Example was prepared in the same manner as in Example 1 using the adhesive composition of this
  • the storage modulus of this heat-bonding film adhesive was measured at each temperature in the same manner as in Example 1. The results are shown in Table 1.
  • the heat-bonding film adhesives of Examples 2, 3, and 4 were easily heat cured at a temperature of 120°C or higher, and their storage moduli at 280°C were all larger than 10 ⁇ dyne/cm 2 .
  • Example 5 A heat-bonding film adhesive of this Example was formed in the same manner as in
  • Example 1 except that the film adhesive was stored at room temperature (about 25°C) for
  • the storage modulus of this heat-bonding film adhesive was measured in the same manner as in Example 1.
  • the heat-bonding film adhesive of the present invention could be stably stored after the activation, and was easily heat cured at a temperature of 120°C or higher.
  • the storage modulus at 280°C was larger than 10 ⁇ dyne/cm 2 .

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Abstract

L'invention porte sur une composition adhésive thermofusible à durcissement rapide, ne demandant pas d'eau pour prendre ni de solvant pour former une pellicule, de bonne stabilité au stockage, et convenant pour le collage des composants électroniques ou la constitution de boîtiers de CI. Ladite composition comprend spécifiquement un copolymère de polyéthylène présentant comme composant époxy des groupes époxy dans une molécule, ainsi qu'un catalyseur cationique de polymérisation. L'invention porte également sur des films adhésifs collant à chaud et sur des procédés d'utilisation de la composition adhésive thermofusible.
PCT/US1999/013468 1998-06-29 1999-06-15 Composition adhesive thermofusible, adhesif collant a chaud et procede de collage a l'aide de la composition adhesive thermofusible WO2000000566A1 (fr)

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US09/355,602 US6265460B1 (en) 1998-06-29 1999-06-15 Hot-melt adhesive composition, heat-bonding film adhesive and adhering method using hot-melt adhesive composition

Applications Claiming Priority (2)

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JP10182091A JP2000017242A (ja) 1998-06-29 1998-06-29 ホットメルト接着剤組成物、熱圧着性フィルムおよびホットメルト接着剤組成物を用いた接着方法
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WO2003035744A1 (fr) * 2001-10-24 2003-05-01 Sumitomo Chemical Company, Limited Composition de resine thermodurcissable
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WO2005063907A1 (fr) * 2003-12-23 2005-07-14 Tesa Ag Colle à fusion
WO2005063908A1 (fr) * 2003-12-23 2005-07-14 Tesa Ag Colle fusible
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