EP0585360A1 - Uaf epoxidbasierende klebstoffe - Google Patents
Uaf epoxidbasierende klebstoffeInfo
- Publication number
- EP0585360A1 EP0585360A1 EP92912359A EP92912359A EP0585360A1 EP 0585360 A1 EP0585360 A1 EP 0585360A1 EP 92912359 A EP92912359 A EP 92912359A EP 92912359 A EP92912359 A EP 92912359A EP 0585360 A1 EP0585360 A1 EP 0585360A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- adhesive
- weight
- epoxide
- parts
- component
- 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.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
- B41M7/0045—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using protective coatings or film forming compositions cured by mechanical wave energy, e.g. ultrasonics, cured by electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams, or cured by magnetic or electric fields, e.g. electric discharge, plasma
-
- 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
- C08G59/68—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 catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/18—Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/22—Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
Definitions
- the present invention relates to epoxide-based adhesives, particularly adhesives whose bond strength is enhanced through photopolymerization.
- the invention also relates to transparent overlays with such adhesive which can be applied to documents to deter tampering.
- PSAs Pressure-sensitive adhesives
- Such adhesives offer advantages of easy application, with successful bonding typically being achieved upon application of limited pressure, e.g., hand pressure. In many cases, such adhesives tend to exhibit reduced bond strength when subjected to elevated temperatures or organic solvents. Although the bond strength of pressure-sensitive adhesives is acceptable for many applications, in some instances, an adhesive that provides useful room temperature tackiness as well as resistance to adhesive failure under elevated temperatures or upon exposure to organic solvents is desired.
- One technique sometimes used to improve the performance, e.g., increase the shear strength and peel resistance, of certain pressure-sensitive adhesives at elevated temperatures or in the presence of organic solvents is to further crosslink the adhesive after its application to a substrate.
- Such crosslinking can be induced photochemically or thermally, or via chemical reaction, e.g., such as with moisture or encapsulated reactants. It has been observed, however, that in some instances crosslinking a pressure-sensitive adhesive results in a reduction in adhesiveness.
- U.S. Patent No. 4,286,047 discloses a normally tacky, pressure-sensitive adhesive having an epoxy equivalent value of about 400 to about 900 which is susceptible to ultraviolet-induced detackification.
- U.S. Patent No. 4,256,828 discloses photocopolymerizable compositions which contain epoxides, organic material with hydroxyl functionality, and a photosensitive aromatic sulfonium or iodonium salt of a halogen-containing complex ion.
- U.S. Patent No. 4,218,531 discloses photopolymerizable compositions containing epoxides, aromatic sulfonium complex salts, and a material containing at least one non-aromatic carbon-carbon ethylenic unsaturation. The reference teaches that such compositions can be cured without generation of offensive odors.
- U.S. Patent No. 4,593,051 discloses photocopolymerizable compositions comprising an epoxide, organic compound having two or more active hydrogens per molecule, and photoinitiator.
- the present invention provides a normally tacky, pressure-sensitive adhesive which, upon exposure to ultraviolet radiation, undergoes crosslinking to result in increased bond strength and bond durability. Bonds made with the adhesive compositions provided herein typically exhibit resistance to failure, e.g., shear release, peel release, or cohesive failure, under elevated temperatures (e.g., about 100°C) and/or exposure to organic solvents. Furthermore, the compositions provided herein exhibit high transparency to visible light both before and after being cured.
- the novel adhesives provided comprise, and if desired may consist essentially of, epoxide resin, polymeric film former, photoinitiator, and polyol.
- Adhesives of the invention may also optionally contain one or more of the following: reactive diluent, solvent, toughening agent, and other additive.
- Adhesives of the present invention typically exhibit an initial tackiness sufficient to provide an initial peel strength of about 0.28 kilograms/centimeter- width (25 ounces/inch-width) when laminated to a stainless steel panel and rolled once with a 2.0 kilogram (4.5 pound) roller.
- the adhesives Prior to being cured, the adhesives provide a low bond strength, i.e., an overlap shear strength of less than about 7.0 kilograms/centimeter 2 (100 pounds/inch 2 ) when laminated between chromic acid etched aluminum panels.
- a bond strength sufficient to provide an overlap shear strength of about 141 kilograms/centimeter 2 (2000 pounds/inch 2 ) on chromic acid etched aluminum may be achieved.
- the epoxide resin is preferably a liquid at room temperature.
- useful epoxide resins include diglycidyl ethers of various phenols, e.g., bisphenol A (“DGEBA”) , hydrogenated bisphenol A (“DGEHBA”) , and bisphenol F (“DGEBF”) ; cycloaliphatic epoxides; epoxide cresol novolac resins; epoxide phenol novolac resins; and the like.
- DGEBA bisphenol A
- DGEHBA hydrogenated bisphenol A
- DGEBF bisphenol F
- cycloaliphatic epoxides epoxide cresol novolac resins
- epoxide phenol novolac resins epoxide phenol novolac resins
- Such epoxide resins may be used singly or in combinations of two or more.
- DGEBA resins are commonly available, e.g., from Shell Chemical Company, Dow Chemical Company, and Ciba Geigy Company. Typically, low molecular weight DGEBA resins with an epoxy equivalent weight of below about 280 are preferred. DGEBA resins with epoxy equivalent weights substantially above that range, e.g., above about 300 or more, typically tend to be more solid in character and less liquid in character at room temperature, thereby reducing the desired tackiness of the composition.
- cycloaliphatic epoxide resins useful herein include those having an average of two or more epoxide groups per molecule.
- the preferred cycloaliphatic epoxide is 3,4-epoxide cyclohexylmethyl -3,4-epoxidecyclohexane carbox late, e.g., available commercially as EPOXIDE ERL 4221 from Union Carbide Company. Readily available, this is a fast reacting, low viscosity resin.
- Bis(3,4-epoxidecyclo-hexylmethyl) adipate is an illustrative example of a cycloaliphatic epoxide resin which is useful herein.
- Phenol-novolac and cresol-novolac epoxide resins are multifunctional resins derived from epichlorohydrin and polynuclear phenolic or cresol novolac. They are typically characterized by low amounts of ionic and hydrolyz ble chlorine impurities and high chemical and thermal resistance. Illustrative examples of commercially available supplies thereof include Ciba-Geigy's EPN and ECN Epoxide Resin series. Adhesive compositions of the present invention may contain one or more of the epoxide resins described above.
- the room temperature viscosity of the epoxide resin mixture is between about 1,000 and about 30,000 centipoise, preferably between about 3,000 and about 20,000 centipoise.
- Adhesive compositions made with epoxide resins having viscosities which are too high may tend to exhibit undesirably low tack, whereas those made with epoxide resins having viscosities which are too low may tend to be subject to resin migration and phase separation.
- the polymeric film former is a polymeric material having a molecular weight which is higher than that of the epoxide resin component.
- the film former should be compatible with the epoxide resin, i.e., they should not undergo phase separation such as during storage of the resultant adhesive composition or of an article comprising same. Polymeric materials which can form a tough film at room temperature are preferred.
- the film former preferably has a weight average molecular weight between about 10,000 and about 30,000. Adhesive compositions made with film formers having molecular weights which are too low tend to provide poorer peel strength prior to photopolymerization. Adhesive compositions made with film formers having molecular weights which are too high may be harder to make as the film former is typically more difficult to handle, to dissolve, etc., and may be too viscous.
- polymeric film formers which are useful herein include polyacrylates, polymethacrylates, phenoxy resins, polysulfones, and polyether sulfones.
- adhesives of the invention will depend in part upon the nature of the epoxide component, the particular film former, and the degree of room temperature tackiness desired.
- adhesives of the invention will contain between about 15 and about 100, preferably between about 20 and about 80, and most preferably between about 40 and about 60, parts by weight of film former per 100 parts by weight of epoxide component.
- Adhesive compositions of the invention typically contain a polyol component to increase the initial tackiness, post cure flexibility, and open time of the adhesive composition.
- Illustrative examples of polyols which are useful in adhesive compositions of the invention include the following: polyether polyol, polyester polyol, polycaprolactone polyol.
- the aforementioned U.S. Patent Nos. 4,256,828 and 4,593,051 disclose polyols which are useful in photopolymerizable epoxide compositions.
- Adhesive compositions of the invention typically contain between about 2 and about 20 parts, preferably between about 3 and about 15 parts, and more preferably between about 4 and about 10 parts, by weight of polyol per 100 parts by weight of epoxide component. Adhesive compositions containing too much polyol tend to undergo ultraviolet curing more slowly and, once cured, exhibit lower peel strengths. Adhesive compositions containing too little polyol may not cure completely, even with thermal post treatment.
- photoinitiators known for use in photopolymerizable epoxide compositions may be used in adhesive compositions of the invention. Illustrative examples are disclosed in the aforementioned U.S. Patent Nos. 4,231,951 and 4,256,828 and U.S. Patent No. 4,058,401 (Crivello) .
- Preferred photoinitiators include triaryl sulfonium salts and diaryl iodonium complex salts. These photoinitiators are typically thermally stable and readily available commercially and exhibit good ultraviolet reactivity.
- Adhesive compositions of the invention typically contain between about 1 and about 10, preferably between about 1.5 and about 6, and more preferably between about 2 and about 4, parts by weight of photoinitiator per 100 parts by weight of epoxide component. Use of excessive amounts of photoinitiator may act as a screen, thereby impairing the desired photopolymerization of the adhesive. Also, large residual amounts of unused initiator may tend to impair the bonding characteristics of the cured adhesive. If desired, adhesive compositions of the invention may also contain one or more of such additives as metal particles, metal-coated particles, coloring agents, processing aids, adhesion promoters, wetting agents, and coupling agents.
- Metal particles and metal-coated particles can be incorporated to render the adhesive composition conductive including anisotropically conductive if desired.
- Illustrative examples include nickel particles between about 6 and about 25 microns in diameter which can be randomly dispersed in the composition.
- the adhesive composition may be substantially clear and colorless or may be colored by use of such coloring agents as dyes and pigments. It will be understood, however, that coloring agents may tend to increase the opacity of the adhesive composition so as to affect the photocuring properties thereof, particularly when the adhesive is used in thick layers. Accordingly, coloring agents used herein should be selected and used in such quantities as will not undesirably inhibit the photocuring properties of the adhesive composition.
- Adhesive compositions of the invention may contain processing aids and modifiers, e.g., rheology controlling agents such as fumed silica. Illustrative examples of adhesion promoters and coupling agents include silanes and titanates. Fluorochemical and other surface energy controlling agents may be used.
- the various components used in compositions of the invention are preferably compatible with each other such that the cured adhesive is substantially transparent, thereby permitting the composition to be used in overlays, e.g. , over information on documents.
- Adhesives of the invention may be supplied in film form, e.g., between release liners as a transfer tape, to be laminated to a substrate. Photopolymerization of the composition may be performed after the various elements are assembled, e.g., by exposure to ultraviolet radiation through a substrate which is sufficiently transparent to such wavelengths, or the adhesive may be exposed prior to assembly. Under typical conditions, e.g., temperature of about 25°C, relative humidity of about 60 percent, and UV exposure of about 0.1 Joule/centimeter 2 , adhesive compositions of the invention typically exhibit an open time of about 1 to 2 minutes. Adhesive compositions of the invention can be used to bond substrates that previously known thermally cured epoxide adhesives bonded, simultaneously providing the advantages discussed herein.
- adhesives of the invention may optionally be heated, i.e., thermally postcured or thermal post treatment, to enhance the structural bond strength of the bond. Typically, such treatment involves heating the adhesive to a temperature of about 100°C to about 120°C for several minutes.
- adhesives of the invention can be used to make transparent overlays for making documents more tamper-resistant.
- One typical embodiment of such overlays comprises a protective cover sheet such as disclosed in U.S. Patent No. 3,170,183 (Sevelin et al.), incorporated herein by reference, with a layer of the adhesive provided herein on the back side.
- the cover sheet may simply be single or multi-ply polymer film, e.g., polyester, which is typically preferably flexible and abrasion resistant.
- Overlap Shear Strength Overlap Shear Strength of indicated adhesives was determined using aluminum panels having an overlap region of about 1.0 inch by about 0.5 inch (2.5 by 1.3 centimeters) .
- the aluminum panels were conditioned in chromic acid at a temperature of about 65°C to about 70°C for about 15 minutes and then rinsed with tap water. The panels were then allowed to dry at room temperature for about 30 minutes and then at about 60°C to about 65°C for 30 minutes.
- the subject adhesive was applied to a test panel at a thickness of about 1 to about 2 mils (25 to 50 microns) , activated with ultraviolet radiation as indicated, and then the second panel laminated thereto. Unless otherwise indicated, the bond was then thermally postcured at about 110°C to about 115°C for 20 minutes.
- Adhesives were made using the following components: N Noottaattiioonn Explanation EPON 828 DGEBA resin from Shell Chemical
- NIAX PPG 4025 Polypropylene glycol from Union Carbide Company
- the adhesive compositions were cured with a 200 Watts/inch electrodeless mercury lamp in a UV processor. The exposure was measured with a UV-A radiometer to be about 0.050 Joules/centimeter 2 .
- the joints were thermally postcured under slight compression pressure using small binder clips. In each sample, the adhesive composition was substantially transparent before and after cure.
- Example 5 Adhesive of the same composition as in Example
- the adhesive was activated with exposure to a 200 Watt/inch mercury lamp with total energy output of about 0.050 Joules/centimeter 2 .
- a flexible printed circuit was laminated to the adhesive under about 30 kilograms/centimeter 2 pressure at about 110°C for 10 seconds. The laminates were postcured at 110°C for 20 minutes.
- the resistance between the flexible printed circuit leads and gold circuit board was 0.2 ohms or less.
- the resistance between the adjacent leads of the printed circuit was greater than 20 mega ohms, the maximum value of the ohm meter used. This demonstrates the highly anisotropic conductivity properties which may be obtained with adhesives of the invention.
- the adhesive was coated with a knife coater onto the bottom side of 3M CONFIRM Brand Retroreflective Security Laminate from which the commercially-shipped adhesive had been removed to provide a dry thickness between about l and about 2 mils (25 to 50 micrometers) .
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Electromagnetism (AREA)
- Mechanical Engineering (AREA)
- Plasma & Fusion (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70111991A | 1991-05-16 | 1991-05-16 | |
US701119 | 1991-05-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0585360A1 true EP0585360A1 (de) | 1994-03-09 |
Family
ID=24816150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92912359A Ceased EP0585360A1 (de) | 1991-05-16 | 1992-03-12 | Uaf epoxidbasierende klebstoffe |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0585360A1 (de) |
JP (1) | JPH06507664A (de) |
CA (1) | CA2108260A1 (de) |
WO (1) | WO1992020754A1 (de) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7575653B2 (en) | 1993-04-15 | 2009-08-18 | 3M Innovative Properties Company | Melt-flowable materials and method of sealing surfaces |
CA2115888A1 (en) | 1993-04-15 | 1994-10-16 | Clayton A. George | Epoxy/polyester hot melt compositions |
US5436063A (en) * | 1993-04-15 | 1995-07-25 | Minnesota Mining And Manufacturing Company | Coated abrasive article incorporating an energy cured hot melt make coat |
US5362421A (en) * | 1993-06-16 | 1994-11-08 | Minnesota Mining And Manufacturing Company | Electrically conductive adhesive compositions |
JP4539644B2 (ja) * | 1993-07-29 | 2010-09-08 | 日立化成工業株式会社 | 回路接続材料とその接続材料を用いた回路の接続方法 |
JPH09176606A (ja) * | 1995-12-22 | 1997-07-08 | Sumitomo Bakelite Co Ltd | 光学部品固定用接着剤 |
DE19629750A1 (de) * | 1996-07-23 | 1998-01-29 | Siemens Ag | Thermisch härtbares einkomponentiges Low Viskosity Adhesive-Klebstoffsystem mit verbesserten Lagerungseigenschaften |
US5964979A (en) | 1997-08-15 | 1999-10-12 | 3M Innovative Properties Company | Sealing method and article |
US6228133B1 (en) | 1998-05-01 | 2001-05-08 | 3M Innovative Properties Company | Abrasive articles having abrasive layer bond system derived from solid, dry-coated binder precursor particles having a fusible, radiation curable component |
US6057382A (en) * | 1998-05-01 | 2000-05-02 | 3M Innovative Properties Company | Epoxy/thermoplastic photocurable adhesive composition |
US6136398A (en) * | 1998-05-01 | 2000-10-24 | 3M Innovative Properties Company | Energy cured sealant composition |
US6077601A (en) | 1998-05-01 | 2000-06-20 | 3M Innovative Properties Company | Coated abrasive article |
US6274643B1 (en) | 1998-05-01 | 2001-08-14 | 3M Innovative Properties Company | Epoxy/thermoplastic photocurable adhesive composition |
JP2000154352A (ja) * | 1998-11-18 | 2000-06-06 | Sekisui Chem Co Ltd | 反応性ホットメルト接着剤組成物及び接着方法 |
JP2000212540A (ja) * | 1999-01-28 | 2000-08-02 | Sekisui Chem Co Ltd | 反応性ホットメルト接着剤組成物及び接着方法 |
JP2002047474A (ja) * | 2000-07-31 | 2002-02-12 | Toppan Forms Co Ltd | カチオン系光架橋型接着剤およびそれを用いた接着シート |
JP2002047456A (ja) * | 2000-07-31 | 2002-02-12 | Toppan Forms Co Ltd | ラジカル系光架橋型接着剤およびそれを用いた接着シート |
US20020182955A1 (en) * | 2001-03-29 | 2002-12-05 | Weglewski James T. | Structural bonding tapes and articles containing the same |
JP4384509B2 (ja) * | 2003-01-09 | 2009-12-16 | 積水化学工業株式会社 | 有機エレクトロルミネッセンス素子の封止方法及び有機エレクトロルミネッセンス素子 |
EP1710286A1 (de) | 2005-04-04 | 2006-10-11 | 3M Innovative Properties Company | Verstärkungskissen |
EP2812393B1 (de) | 2012-02-06 | 2023-07-12 | Westlake Epoxy Inc. | Epoxidharzformulierungen für textilien, matten und andere faserverstärkungen für verbundanwendungen |
KR102334119B1 (ko) * | 2014-03-07 | 2021-12-01 | 헨켈 아게 운트 코. 카게아아 | 광경화성 에폭시 수지 시스템 |
WO2016196561A1 (en) | 2015-06-04 | 2016-12-08 | 3M Innovative Properties Company | Methods of bonding hardware to vehicular glass |
WO2017174303A1 (de) | 2016-04-04 | 2017-10-12 | Tesa Se | Strahlenaktivierbares haftklebeband mit dunkelreaktion und dessen verwendung |
CN112011293B (zh) * | 2019-05-28 | 2022-10-04 | 3M创新有限公司 | 可固化压敏胶组合物,可固化压敏胶带和电池组 |
EP3976724A4 (de) * | 2019-05-28 | 2023-06-14 | 3M Innovative Properties Company | Härtbare druckempfindliche klebstoffzusammensetzung, härtbares druckempfindliches klebeband und batteriesatz |
CN112795345B (zh) * | 2021-01-29 | 2022-09-27 | 浙江中特化工有限公司 | 一种uv延迟固化胶粘剂及其制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1194637A (en) * | 1982-04-26 | 1985-10-01 | Charles R. Morgan | Uv and thermally curable, thermoplastic-containing compositions |
US4585534A (en) * | 1983-04-29 | 1986-04-29 | Desoto, Inc. | Optical glass fiber coated with cationically curable polyepoxide mixtures |
CA1304865C (en) * | 1985-12-20 | 1992-07-07 | Kollmorgen Technologies Corporation | Heat activatable adhesive for wire scribed circuits |
US4690957A (en) * | 1986-02-27 | 1987-09-01 | Mitsubishi Denki Kabushiki Kaisha | Ultra-violet ray curing type resin composition |
EP0485508A1 (de) * | 1989-08-01 | 1992-05-20 | H.B. FULLER LICENSING & FINANCING, INC. | Flüssige hitzehärtbare zusamensetzung |
-
1992
- 1992-03-12 CA CA002108260A patent/CA2108260A1/en not_active Abandoned
- 1992-03-12 WO PCT/US1992/001974 patent/WO1992020754A1/en not_active Application Discontinuation
- 1992-03-12 EP EP92912359A patent/EP0585360A1/de not_active Ceased
- 1992-03-12 JP JP4511128A patent/JPH06507664A/ja active Pending
Non-Patent Citations (1)
Title |
---|
See references of WO9220754A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1992020754A1 (en) | 1992-11-26 |
CA2108260A1 (en) | 1992-11-17 |
JPH06507664A (ja) | 1994-09-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0585360A1 (de) | Uaf epoxidbasierende klebstoffe | |
CN1322580C (zh) | 胶粘带 | |
CA1289688C (en) | Shrinkage-resistant ultraviolet-curing coatings | |
US6277481B1 (en) | Adhesive composition and adhesive sheet | |
US6254954B1 (en) | Pressure-sensitive adhesive tape | |
EP0963421B1 (de) | Druckempfindliches klebeband | |
WO2000046318A1 (en) | Pressure sensitive adhesive tape | |
CA2028259A1 (en) | Tacky photopolymerizable adhesive compositions | |
US7695586B2 (en) | Photosensitive epoxy resin adhesive composition and use thereof | |
JPH09291268A (ja) | 接着剤組成物および該組成物からなる接続部材 | |
JP3651624B2 (ja) | 回路用接続部材 | |
JPH11508301A (ja) | 接着組成物、接着組成物から製造された接着フィルムおよび接着フィルムの製造方法 | |
EP0942054A1 (de) | Mehrschichtige Klebestruktur | |
TW201144401A (en) | Composition and adhesive | |
JP4094080B2 (ja) | 接着剤組成物および接着シート | |
JP2000144071A (ja) | 光重合性組成物、光硬化型粘接着シート及び部材の接合方法 | |
WO2002055625A1 (fr) | Composition d'adhesif thermofusible photoreactif | |
JP4001677B2 (ja) | 熱硬化型接着剤組成物とその接着シ―ト類 | |
JPH1121536A (ja) | 硬化型粘接着剤組成物、硬化型粘接着シート及び電子材料部材の接着方法 | |
JPH11106731A (ja) | 回路接続用組成物及びこれを用いたフィルム | |
EP1219694A1 (de) | Photovernetzbare druckempfindliche klebstoffzusammensetzung und druckempfindliche klebstofffolie | |
JP4006035B2 (ja) | 熱硬化型シリコーン粘接着剤 | |
JPH10251614A (ja) | 硬化型粘接着剤組成物 | |
US6641912B2 (en) | Photocurable pressure-sensitive adhesive composition and its sheet | |
JPH10316957A (ja) | 硬化型粘接着剤組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 19931210 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE FR GB IT |
|
17Q | First examination report despatched |
Effective date: 19941130 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED |
|
18R | Application refused |
Effective date: 19950712 |