WO2015115658A1 - アクリル系接着剤の反応率測定方法、及びアクリル系接着剤 - Google Patents

アクリル系接着剤の反応率測定方法、及びアクリル系接着剤 Download PDF

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WO2015115658A1
WO2015115658A1 PCT/JP2015/052928 JP2015052928W WO2015115658A1 WO 2015115658 A1 WO2015115658 A1 WO 2015115658A1 JP 2015052928 W JP2015052928 W JP 2015052928W WO 2015115658 A1 WO2015115658 A1 WO 2015115658A1
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group
acrylic adhesive
reaction rate
compound
fluorene
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PCT/JP2015/052928
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English (en)
French (fr)
Japanese (ja)
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尚也 上澤
雄介 田中
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デクセリアルズ株式会社
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Priority to CN201580007074.0A priority Critical patent/CN105940299B/zh
Priority to KR1020167015172A priority patent/KR102368125B1/ko
Publication of WO2015115658A1 publication Critical patent/WO2015115658A1/ja

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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/04—Preparation or injection of sample to be analysed
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/62—Detectors specially adapted therefor
    • G01N30/74—Optical detectors
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
    • G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
    • G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds
    • G01N2030/8854—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds involving hydrocarbons

Definitions

  • the present invention relates to a method for measuring a reaction rate of an acrylic adhesive containing a radical polymerizable compound, and an acrylic adhesive.
  • anisotropic conductive films are widely used as electric circuit materials.
  • ACF Anisotropic Conductive Film
  • anisotropic conductive connection in order to connect many electrodes at once and uniformly, there is a difference in the reaction rate between the electrodes with relatively high thermal conductivity and between the electrodes with relatively low thermal conductivity. Seems to occur.
  • the present invention has been proposed in view of such a conventional situation.
  • a reaction rate measuring method capable of accurately measuring a reaction rate of an acrylic adhesive even with a small amount of sample, and an acrylic adhesive. provide.
  • reaction rate can be accurately measured even with a very small amount of sample by using a compound having a fluorene skeleton as an internal standard substance.
  • the reaction rate measurement method uses a compound having a fluorene skeleton represented by the following formula (1) as an internal standard substance, separates a sample solution containing an acrylic adhesive by liquid chromatography, and detects ultraviolet rays. An unreacted radical polymerizable compound is detected by a vessel.
  • R 1 is a group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, and an alkoxy group having 1 to 3 carbon atoms
  • R 2 is a hydroxyl group, having 1 to 3 carbon atoms.
  • the acrylic adhesive according to the present invention is characterized by containing a compound having a fluorene skeleton represented by the formula (1), a radical polymerizable compound, and a reaction initiator.
  • the anisotropic conductive adhesive according to the present invention is characterized in that conductive particles are dispersed in the acrylic adhesive.
  • the compound having a fluorene skeleton exhibits high sensitivity to the ultraviolet detector, the reaction rate can be accurately measured even with a very small amount of sample. Further, since the compound having a fluorene skeleton does not participate in the curing reaction of the acrylic adhesive, it can be blended in advance with the acrylic adhesive.
  • FIG. 1 is a chromatogram showing an example of an analysis result of an acrylic adhesive before curing.
  • FIG. 2 is a chromatogram showing an example of the analysis result of the acrylic adhesive after curing.
  • Method for measuring reaction rate of acrylic adhesive In the method for measuring the reaction rate of an acrylic adhesive according to the present embodiment, a compound having a fluorene skeleton represented by the following formula (1) is used as an internal standard substance, and a sample solution containing the acrylic adhesive is subjected to liquid chromatography. Separate and detect unreacted radical polymerizable compound by ultraviolet detector.
  • BPEF bisphenoxyethanol fluorene
  • BCF biscresol fluorene
  • BHT dibutylhydroxytoluene
  • BTZ benzotriazole
  • BHT has low versatility because the peak detection position overlaps with bisphenoxyethanol fluorene acrylate (BPEFA) and BTZ with 4-hydroxybutyl acrylate (4-HBA).
  • Liquid chromatography is high-performance liquid chromatography (HPLC: High Performance Liquid Chromatography), and the sample solution is passed through a separation column packed with a separation agent, and the difference in distribution to the separation agent, the degree of ease of adsorption, etc. Is separated into a plurality of components.
  • HPLC High Performance Liquid Chromatography
  • the separating agent examples include silica gel having a particle size of about 2 to 30 ⁇ m for HPLC, chemically bonded silica gel bonded with a group such as octadecyl group, cyanopropyl group, porous polymer, ion exchange resin, and the like. Can do.
  • the ultraviolet detector is not particularly limited as long as it irradiates the sample solution with ultraviolet light and measures the absorbance of the sample solution, and an ultraviolet absorbance detector that is widely used for analysis by HPLC should be used. Can do.
  • a predetermined amount of a compound having a fluorene skeleton may be added to an acrylic adhesive in advance, or a predetermined amount of a compound having a fluorene skeleton may be added to a sample solution of the acrylic adhesive.
  • a solvent for dissolving the acrylic adhesive acetonitrile, acetone or the like can be used.
  • FIG. 1 and FIG. 2 are chromatograms showing examples of the analysis results of the acrylic adhesive before and after curing, respectively.
  • the peak intensity of the chromatogram obtained by the ultraviolet detector is usually represented by the peak area or peak height.
  • a method for calculating the reaction rate based on the peak height will be described.
  • the strength ratio between the internal standard substance and the unreacted monomer is determined from the chromatograms of the acrylic adhesive before curing and the acrylic adhesive after complete curing.
  • the curing rate is 0% before curing and complete curing.
  • a relationship line between the intensity ratio and the reaction rate is created.
  • the intensity ratio between the internal standard substance and the unreacted monomer can be obtained from the chromatogram of the unknown sample, and the reaction rate can be obtained from the created relationship line.
  • reaction rate can be accurately measured even with a small amount of sample.
  • the acrylic adhesive according to the present embodiment contains a compound having a fluorene skeleton represented by the following formula (1), a radical polymerizable compound, and a reaction initiator.
  • an anisotropic conductive adhesive in which conductive particles are dispersed in an acrylic adhesive will be described. Even if the compound having a fluorene skeleton represented by the formula (1) is blended in an anisotropic conductive adhesive, it does not decompose during thermocompression bonding and does not participate in the curing reaction. High sensitivity can be shown to the detector. For this reason, if this anisotropic conductive adhesive is used, the reaction rate of minute regions on the electrodes and between the electrodes can be accurately measured.
  • the compounding amount of the compound having a fluorene skeleton is preferably 0.01 wt% or more and 5.0 wt% or less, and more preferably 0.2 wt% or more and 1.0 wt% or less.
  • the blending amount is too small, the measurement peak becomes small and does not function as an internal standard substance.
  • the blending amount is too large, the characteristics as an anisotropic conductive film are deteriorated.
  • radical polymerizable compound a monofunctional (meth) acrylate monomer, a polyfunctional (meth) acrylate monomer, or a modified monofunctional in which an epoxy group, a urethane group, an amino group, an ethylene oxide group, a propylene oxide group, or the like is introduced, Alternatively, a polyfunctional (meth) acrylate monomer can be used. Moreover, the radically polymerizable compound can be used in any state of a monomer or an oligomer, and a monomer and an oligomer can be used in combination.
  • Examples of the (meth) acrylate monomer include (meth) acrylate resins having at least one (meth) acryloyl group in one molecule and modified products thereof.
  • Examples of the modified products include tetrahydrofurfuryl acrylate, isobornyl acrylate, methyl methacryl acrylate, ethyl methacryl acrylate, tricyclodecane dimethanol diacrylate, tricyclodecane dimethanol dimethacrylate, ethoxylated bisphenol A diacrylate, Examples include propoxylated bisphenol A diacrylate, pentaerythritol triacrylate, and ethoxylated isocyanuric acid triacrylate. You may use these 1 type or in mixture of 2 or more types.
  • an organic peroxide As the reaction initiator, an organic peroxide, a photo radical polymerization initiator, or the like can be used.
  • an organic peroxide 1 type (s) or 2 or more types can be used from diacyl peroxide, dialkyl peroxide, peroxy dicarbonate, peroxy ester, peroxy ketal, hydroperoxide, silyl peroxide, and the like.
  • Photo radical polymerization initiators include benzoin ethers such as benzoin ethyl ether and isopropyl benzoin ether, benzyl ketals such as benzyl and hydroxycyclohexyl phenyl ketone, ketones such as benzophenone and acetophenone and derivatives thereof, thioxanthones, and bisimidazoles. 1 type, or 2 or more types can be used from these.
  • conductive particles used in conventional anisotropic conductive films can be used.
  • metal particles such as gold particles, silver particles and nickel particles, resins such as benzoguanamine resins and styrene resins.
  • Metal-coated resin particles whose surfaces are coated with a metal such as gold, nickel, or zinc can be used.
  • the average particle size of such conductive particles is usually 1 to 10 ⁇ m, more preferably 2 to 6 ⁇ m.
  • the anisotropic conductive adhesive may contain a film-forming resin, a silane coupling agent, a phosphate ester, an inorganic filler, a stress relaxation agent, and the like.
  • the film-forming resin include phenoxy resin, polyvinyl acetal resin, polyvinyl butyral resin, alkylated cellulose resin, polyester resin, acrylic resin, styrene resin, urethane resin, and polyethylene terephthalate resin.
  • silane coupling agents include ⁇ -glycidpropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -ureidopropyltriethoxysilane, N- ⁇ -aminoethyl- ⁇ -amino.
  • Examples thereof include propyltrimethoxysilane and ⁇ -methacryloxypropyltrimethoxysilane.
  • Example> Examples of the present invention will be described below.
  • bisphenol ethanol fluorene (BPEF) was used as an internal standard substance
  • the reaction rate of the acrylic anisotropic conductive adhesive was measured by HPLC (High performance liquid chromatography), and the standard deviation was evaluated.
  • the standard deviation of the reaction rate measured by DSC (Differential scanning calorimetry) and FT-IR (Fourier Transform Infrared Spectroscopy) was also evaluated.
  • DSC Different scanning calorimetry
  • FT-IR Fastier Transform Infrared Spectroscopy
  • An anisotropic conductive film and a mounting body were produced as follows.
  • anisotropic conductive adhesive having the following composition was used.
  • the formulation is 40 parts by mass of phenoxy resin (trade name: YP50, Nippon Steel & Sumikin Chemical Co., Ltd.), 40 parts by mass of polyurethane (trade name: N-5196, Nippon Polyurethane Industry Co., Ltd.), phosphate ester (trade name: PM -2, Nippon Kayaku Co., Ltd.) 2 parts by weight, Silane coupling agent (trade name: A-187, Momentive Performance Materials Co., Ltd.) 2 parts by weight, bifunctional acrylate (trade name: DCP, Shin Nakamura) Chemical Industry Co., Ltd.) 3 parts by mass, acrylic ester (trade name: SG-P3, (Nagase Chemtex Co., Ltd.) 5 parts by mass, diacyl peroxide (trade name: Parroyl L, Nippon Oil & Fats Co., Ltd.) 5 parts by mass And a total of 100 parts
  • a glass substrate ITO solid glass, 10 ⁇ / ⁇ , 0.7 mmt
  • An anisotropic conductive film was affixed on a glass substrate and heated and pressurized under the conditions of 45 ° C., 1 MPa, and 2 seconds, and then the PET was peeled off and temporarily bonded.
  • An FPC was placed on the anisotropic conductive film and heated and pressed under the conditions of a predetermined temperature, 2 MPa, and 5 seconds to obtain a mounted body.
  • HPLC HPLC
  • Waters UPLC UV detector connection
  • a 0.005 mg sample for measurement was dissolved in acetonitrile, and this was injected into a separation column (10 cm, 40 ° C.) to obtain a chromatogram.
  • the analysis conditions were as follows.
  • the measured intensity ratio between BPEF and acrylic monomer was determined from the obtained chromatogram, and the reaction rate was determined from the relationship line between the measured intensity ratio between BPEF and acrylic monomer prepared in advance and the reaction rate. The above operation was repeated three times.
  • the measurement results of the reaction rate when the pressure bonding temperature is 130 ° C. are 78.5% for the first time, 79.4% for the second time, and 79.2% for the third time, and the standard deviation is 0.4726.
  • the measurement results of the reaction rate when the pressure bonding temperature is 140 ° C. are 86.3% for the first time, 86.8% for the second time, and 85.2% for the third time, and the standard deviation is 0.8185. It was.
  • the measurement results of the reaction rate when the pressure bonding temperature was 150 ° C. were 91.1% for the first time, 92.0% for the second time, and 91.0% for the third time, and the standard deviation was 0.5508.
  • An uncured (before crimping) sample was used as a reference.
  • the difference between the calorific value of the uncured sample and the calorific value of the unknown sample after pressure bonding was determined, and the calorific value of the uncured sample was taken as 1, and the reaction rate of the unknown sample was calculated.
  • the emitted-heat amount was calculated
  • the measurement results of the reaction rate when the pressure bonding temperature is 130 ° C. are 72.0% for the first time, 83.2% for the second time, and 75.7% for the third time, and the standard deviation is 5.7064.
  • the measurement results of the reaction rate when the pressure bonding temperature is 140 ° C. are 82.6% for the first time, 78.9% for the second time, and 88.1% for the third time, and the standard deviation is 4.6293. It was.
  • the measurement results of the reaction rate when the pressure bonding temperature was 150 ° C. were 94.2% for the first time, 86.8% for the second time, and 90.2% for the third time, and the standard deviation was 3.7041.
  • FT-IR Using a Fourier transform infrared spectrophotometer (FT / IR-4100, manufactured by JASCO Corporation), 0.02 mg of a measurement sample was measured by the transmission method.
  • the reaction rate of the unknown sample was calculated from the ratio of the measured strength of the acrylic monomer (unsaturated group) of the uncured (before pressure bonding) sample to the measured strength of the acrylic monomer (unsaturated group) of the unknown sample after pressure bonding. .
  • the measurement results of the reaction rate when the pressure bonding temperature is 130 ° C. are the first time 68.7%, the second time 79.6%, and the third time 74.2%, and the standard deviation is 5.4501.
  • the measurement results of the reaction rate when the pressure bonding temperature is 140 ° C. are 77.8% for the first time, 82.0% for the second time, and 89.7% for the third time, and the standard deviation is 6.0352. It was.
  • the measurement results of the reaction rate when the pressure bonding temperature was 150 ° C. were 88.8% for the first time, 87.3% for the second time, and 93.8% for the third time, and the standard deviation was 3.4034.
  • a mounting body was prepared using an anisotropic conductive film containing 0.5 wt% of BPEF, and then the reaction rate of the anisotropic conductive film was measured using HPLC.
  • the FPC is peeled off from the mounting body, and the measurement sample on the wiring of 2.0 mm ⁇ 0.2 mm, the measurement sample of the inter-wiring measurement of 2.0 mm ⁇ 0.2 mm, and the measurement sample on the wiring and between the wirings Sampling was performed.
  • HPLC HPLC
  • Waters UPLC UV detector connection
  • a 0.005 mg sample for measurement was dissolved in acetonitrile, and this was injected into a separation column (10 cm, 40 ° C.) to obtain a chromatogram.
  • the analysis conditions were as follows.
  • the measured intensity ratio between BPEF and acrylic monomer was determined from the obtained chromatogram, and the reaction rate was determined from the relationship line between the measured intensity ratio between BPEF and acrylic monomer prepared in advance and the reaction rate. The above operation was repeated a total of 3 times to obtain an average value.
  • an environmental test 60 ° C., 95%, 500 hr was performed on the mounting body manufactured using the anisotropic conductive film containing 0.5 wt% of BPEF, and the conduction resistance was measured.
  • the conduction resistance was measured by a 4-terminal method using a digital multimeter (digital multimeter 7561, manufactured by Yokogawa Electric Corporation).
  • the reliability test was evaluated as “NG” when the conduction resistance was 3 ⁇ or more and “OK” when the conduction resistance was less than 3 ⁇ .
  • the evaluation of the appearance of the anisotropic conductive film part of the mounting body was visually observed as “ ⁇ ” when there was no bubble, “ ⁇ ” when there was a small bubble, “ ⁇ ” when there was a large bubble, and floating. The case was set as “x”.
  • the peel strength (JIS K6854) of the mounted body is evaluated as “ ⁇ ”when the 90 ° peel strength is 10 N / 25 mm or more, and“ ⁇ ”when the 90 ° peel strength is 8 N / 25 mm or more and less than 10 N / 25 mm.
  • the evaluation of indentation is “ ⁇ ” when the conduction resistance of the mounting body is 1 ⁇ or less, “ ⁇ ” when it is 1 ⁇ or more and less than 2 ⁇ , “ ⁇ ” when it is 2 ⁇ or more and less than 5 ⁇ , “ ⁇ ”, 5 ⁇ or more The thing which is made into "x”.
  • the conduction resistance was measured by a 4-terminal method using a digital multimeter (digital multimeter 7561, manufactured by Yokogawa Electric Corporation).
  • the blending amount is preferably 0.01 wt% or more and 5.0 wt% or less, and 0.2 wt% or more and 1. It turned out that it is more preferable that it is 0 wt% or less. It has been found that when the blending amount of BPEF increases, the ease of measurement is improved, but bubbles are generated in the ACF at the time of pressure bonding, and the peel strength and indentability are deteriorated.

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PCT/JP2015/052928 2014-02-03 2015-02-03 アクリル系接着剤の反応率測定方法、及びアクリル系接着剤 WO2015115658A1 (ja)

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CN201580007074.0A CN105940299B (zh) 2014-02-03 2015-02-03 丙烯酸系粘合剂的反应率测定方法和丙烯酸系粘合剂
KR1020167015172A KR102368125B1 (ko) 2014-02-03 2015-02-03 아크릴계 접착제의 반응률 측정 방법, 및 아크릴계 접착제

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