WO2011123321A1 - Pièce composite, précurseur de pièce composite et composition adhésive - Google Patents

Pièce composite, précurseur de pièce composite et composition adhésive Download PDF

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Publication number
WO2011123321A1
WO2011123321A1 PCT/US2011/029742 US2011029742W WO2011123321A1 WO 2011123321 A1 WO2011123321 A1 WO 2011123321A1 US 2011029742 W US2011029742 W US 2011029742W WO 2011123321 A1 WO2011123321 A1 WO 2011123321A1
Authority
WO
WIPO (PCT)
Prior art keywords
composite part
adhesive composition
plastic
polymer network
metal member
Prior art date
Application number
PCT/US2011/029742
Other languages
English (en)
Inventor
Kohichiro Kawate
Sze Ying Lee
Siang Kwang Lee
Original Assignee
3M Innovative Properties 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 3M Innovative Properties Company filed Critical 3M Innovative Properties Company
Publication of WO2011123321A1 publication Critical patent/WO2011123321A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
    • 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
    • C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
    • C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
    • C08J5/121—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives by heating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • 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
    • C08G2270/00—Compositions for creating interpenetrating networks
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • 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
    • C09J2400/00—Presence of inorganic and organic materials
    • C09J2400/10—Presence of inorganic materials
    • C09J2400/16—Metal
    • C09J2400/163—Metal in the substrate

Definitions

  • the present invention relates to a composite part including a metal member and a plastic member bonded to each other, a precursor of the composite part, and a
  • the present invention relates to an adhesive composition wherein a first polymer network and a second polymer network form an interpenetrating polymer network.
  • Japanese Unexamined Patent Application Publication No. S58-125773 describes a heat activatable adhesive composition containing a thermoplastic resin such as a polyester, an epoxy resin, and a thermal initiator.
  • This adhesive composition makes it possible to bond metal or plastic surfaces without having to subject such to a surface pretreatment.
  • This adhesive composition after being applied to the parts to be bonded, forms a thermoset bond when heat is applied thereto by preferably an electromagnetic heating technique.
  • U.S. Patent No. 4,766,183 describes a method for making a one-pack, heat curable composition forming an interpenetrating polymer network of
  • U.S. Patent No. 5,194,503 describes a coating composition used for metals and plastics including a conventional coating composition and from about 2% to about 80% of a modified urethane resin. Summary
  • An object of the present invention is to provide a composite part including a metal and a plastic firmly bonded to each other, a precursor of the composite part
  • Another object of the present invention is to provide an adhesive composition capable of firmly bonding a metal and a plastic.
  • the present invention provides a composite part including a urethane resin having entanglements with a plastic and also with an epoxy-network adhered to the metal member surface, which is obtained by placing a metal member into a molding die and injecting a plastic into the molding die (first aspect).
  • the present invention also provides an adhesive composition including a first polymer network consisting of a urethane resin and a second polymer network consisting of a reactant of an aliphatic amine having an ether framework and an epoxy resin, wherein the first and the second polymer networks form an interpenetrating polymer network.
  • the present invention further provides a composite part precursor including a metal member coated with the adhesive composition.
  • the present invention further provides a composite part including a metal member coated with the adhesive composition and a plastic member (second aspect).
  • the present invention provides a manufacturing method for the composite part including the steps of: preparing a composite part precursor by coating a metal member with the adhesive composition and drying (step 1); and preparing a composite part by placing the composite part precursor in a molding die and injecting a plastic into the molding die (step 2).
  • a composite part including a metal material and a plastic material firmly bonded to each other, a composite part precursor for obtaining the composite part including the metal material and the plastic material firmly bonded to each other, an adhesive composition for firmly bonding the metal material and the plastic material, and a manufacturing method for the composite part.
  • FIG. 1(a) is a diagram showing the peeling strength measurement in Test Example 1.
  • FIG. 1(b) is a diagram showing the shear strength measurement in Test
  • a composite part (first aspect) of the present invention includes a urethane resin having entanglements with a plastic and also with an epoxy-network adhered to the metal member surface, which is obtained by placing a substrate in a molding die and then injecting a plastic into the molding die (via so-called "insert molding").
  • Insert molding is a method derived from plastic injection molding and is a technique for making composite parts wherein an insert product and a plastic are integrated by placing the insert product (in most cases, a metal) in the molding die and then injecting the plastic into the molding die.
  • the urethane resin forms entanglements with the polymer chain of the plastic by heating at the time of insert molding and the entanglements become fixed when fluidity is reduced after cooling of the plastic, thus making it possible to firmly bond the urethane resin and the plastic member to each other.
  • the urethane resin can firmly bond to the metal member surface by forming entanglements with the epoxy-network adhering to the metal member surface. It is thus possible to firmly bond the metal member and the plastic member via the urethane resin and the epoxy-network.
  • the epoxy-network includes the epoxy resin as a constitutional element thereof and refers to a polymer network having a three-dimensional structure.
  • the metal member includes, for example, metals such as aluminum, iron, or copper, or alloys such as stainless steel or duralumin.
  • the plastic member includes conventionally known thermoplastic resins, and is not limited to, for example, polycarbonate, polyurethane, or nylon thermoplastic resins.
  • Adhesive composition is not limited to, for example, polycarbonate, polyurethane, or nylon thermoplastic resins.
  • the present invention relates to an adhesive composition that forms an
  • interpenetrating polymer network including a first polymer network consisting of a urethane resin and a second polymer network consisting of a reactant of an aliphatic amine having an ether framework and an epoxy resin.
  • the first polymer network consists of a urethane resin.
  • the urethane resin is a polymer compound obtained by condensing an isocyanate group and an alcohol group.
  • Specific examples of substances having an isocyanate group include diphenylmethane diisocyanate (MDI), tolylene diisocyanate (TDI), hexamethylene diisocyanate (MDI), xylene diisocyanate (XDI), hydrogenated MDI, hydrogenated TDI, hydrogenated XDI, isophorone diisocyanate, tris(phenyl isocyanate)thiophosphate, burette isocyanates, isocyanate adducts, and the like.
  • MDI diphenylmethane diisocyanate
  • TDI tolylene diisocyanate
  • MDI hexamethylene diisocyanate
  • XDI xylene diisocyanate
  • hydrogenated MDI hydrogenated TDI
  • substances having an alcohol group include polycaprolactone polyols, polycarbonate polyols, polyester polyols, polyether polyols, acryl polyols, epoxy polyols, polyethylene glycol polyols, polypropylene glycol polyols, and the like.
  • the molecular weight of the urethane resin is not limited to, but can be, for example, from several tens of thousands to several million.
  • the second polymer network is an epoxy-network having a three-dimensional structure consisting of the reactant of the aliphatic amine having an ether framework and the epoxy resin. Equimolars of the aliphatic amine having an ether framework and the epoxy resin are preferably included.
  • the aliphatic amine having an ether framework forming the second polymer network preferably includes a diamine that has an ether framework (-0-(CH2)n-)m with an ether bond (-0-) between hydrocarbon chains and that has amine groups at both ends.
  • n and m in the ether framework are arbitrary, n can be from 1 to 5 and m can be from 1 to 10, for example.
  • the amines are not limited to, but can be known amines, for example, polyamide amines obtained by reacting carboxylic acid and an amine having an ether bond, and the like.
  • amine-based curing agents include those sold under product names such as Aradure manufactured by Huntsman Corporation, Ancamide manufactured by Air Products and Chemicals, Inc., Adeka Grandamide manufactured by Adeka
  • epoxy resin forming the second polymer network examples include bisphenol A, bisphenol F, cresol novolac epoxies, phenol novolac epoxies, hydrogenated bisphenol A epoxies, hydrogenated bisphenol F epoxies, alicyclic epoxies, and the like.
  • the molecular weight of the epoxy resin can be from about 200 to about 3000.
  • the terminal amine group and the epoxy group react respectively with the aliphatic amine having an ether framework and the epoxy resin to form the second polymer network, which is the epoxy-network, by amine bonding .
  • the adhesive composition adheres (bonds) to an inorganic material such as a metal or the like by this epoxy-network.
  • glycidoxysilane silane coupling agent KBM403, manufactured by Shin-Etsu Chemical Co., Ltd.
  • Silane coupling agent KBM403 manufactured by Shin-Etsu Chemical Co., Ltd.
  • an interpenetrating polymer network is formed by the first polymer network entering gaps in the three-dimensional second polymer network and there is no covalent bonding between the first and second polymer networks.
  • a flexible structure is maintained even while the first and second polymer networks become structurally complicated and, when contacted by molten plastic, a part of the first polymer network disperses in the polymer forming the plastic material to form entanglements.
  • the plastic is cured, the entangled structure is retained and high adhesive strength between the adhesive composition and the plastic is manifested.
  • the two-dimensional first polymer network is completely dispersed in the plastic and absence of the two-dimensional first polymer network from the metal surface is prevented by the three-dimensional second polymer network bonded to the metal surface.
  • the amount of the urethane resin forming the first polymer network in the interpenetrating polymer network can be from about 85 mass% to about 99 mass%, for example.
  • the amount of the reactant of the aliphatic amine having an ether framework and the epoxy resin forming the second polymer network in the interpenetrating polymer network can be from about 15 mass% to about 1 mass%, for example.
  • the adhesive composition of the present invention can be produced using conventionally known methods.
  • the adhesive composition can be obtained by adding and mixing the epoxy resin, an aliphatic amine compound having an ether structure, and as desired, a coupling agent such as a silane coupling agent or the like to a solution in which the urethane resin has been dissolved in a conventional solvent such as methyl ethyl ketone or the like, and then drying the solvent.
  • a conventional solvent such as methyl ethyl ketone or the like
  • the composite part precursor of the present invention is the adhesive composition coated on a metal member.
  • metal member examples include metals such as aluminum, iron, or copper, or an alloy such as stainless steel or duralumin.
  • the composite part precursor is formed by applying the adhesive composition of the present invention to such metal member so as to have a thickness of from about 5 to about 200 ⁇ after drying.
  • a thickness of from about 5 to about 200 ⁇ after drying By having this thickness, heat stress caused by the difference in the coefficients of thermal expansion of the metal member and the plastic member can be eased, and when subjected to shock by dropping or the like of the composite part including the composite part precursor, peeling of the metal member from the plastic member does not easily occur.
  • Coating of the adhesive composition can be performed by a conventionally known method and there are no particular limitations thereto. Examples of specific coating methods that can be used include screen printing, bar coating, spray coating, dip coating, pad printing, metal mask printing, and the like.
  • the second polymer network (epoxy-network) of the adhesive composition bonds to the metal member surface and has a structure wherein the urethane resin forming the first polymer network has entanglements with the second polymer network.
  • the composite part (second aspect) of the present invention includes a metal member having the adhesive composition coated thereon and a plastic member.
  • the first polymer network formed from the urethane resin has entanglements with the polymer chain forming the plastic member and also with the second polymer network consisting of the reactant of an aliphatic amine having an ether framework and an epoxy resin as described above. Since such adhesive composition is coated on the metal member, the second polymer network bonds to the metal member surface. In the composite part, the metal member and the plastic member are thus firmly bonded to each other via the adhesive composition.
  • metal member examples include metals such as aluminum, iron, or copper, or alloys such as stainless steel or duralumin.
  • plastic member examples include conventionally known thermoplastic resins, and although there are no particularly limitations thereto, polycarbonate, polyurethane, or nylon thermoplastic resins can be used.
  • the composite part can be produced by coating the metal member with the adhesive composition and drying to produce a composite part precursor (the metal member coated with the adhesive composition), and then bonding the plastic member by injection molding to a surface of the composite part precursor coated with the adhesive composition.
  • the composite part can be produced by placing the composite part precursor in a molding die, injecting molten plastic onto the surface of the composite part precursor coated with the adhesive composition, maintaining pressure thereon, and then cooling and then removing it from the die.
  • the composite part can be produced by compressing a plastic film on the surface of the composite part precursor coated with the adhesive composition while heating.
  • the second aspect of the composite part includes one mode of the first aspect of the composite part. That is, composite parts other than the second aspect can be included in the first aspect and composite parts other than the first aspect can be included in the second aspect.
  • the manufacturing method for the composite part of the present invention includes the steps of: preparing a composite part precursor by coating a metal member with the adhesive composition of the present invention and drying (step 1); and preparing a composite part by placing the obtained composite part precursor in a molding die and injecting molten plastic into the molding die (step 2).
  • the composite part can be obtained by this manufacturing method.
  • step 2 by injection of the molten plastic, plastic is introduced into gaps in the network of the adhesive composition and entanglements between the plastic member and the first polymer network of the adhesive composition can be formed.
  • metal member examples include metals such as aluminum, iron, or copper, or alloys such as stainless steel or duralumin.
  • plastic member examples include conventionally known thermoplastic resins, and although there are no particularly limitations thereto, polycarbonate, polyurethane, or nylon thermoplastic resins can be used.
  • the composite part of either aspect of the present invention can be used as a housing for various products in the field of electronic products and components or as a component for use therein.
  • the adhesive composition of the present invention can be used for bonding metal members and plastic members.
  • the composite part precursor of the present invention can be used for producing composite parts.
  • Desmocoll 530-2 Linear hydroxy polyurethane (manufactured by Bayer MaterialScience AG)
  • ZX1059 Epoxy mixture of bisphenol A and bisphenol F (manufactured by Toto Kagaku K.K.)
  • Ancamide 910 Aliphatic diamine compound having an ether structure manufactured by Air Products and Chemicals, Inc.
  • KBM-403 Silane coupling agent (manufactured by Shin-Etsu Chemical Co.,
  • the obtained solution was coated on an aluminum plate having a width a 25 mm, a length of 100 mm, and a thickness of 1.5 mm using a wire bar coater, such that a thickness after drying was from 5 to 10 ⁇ . This was then dried in an oven at 100°C for 30 minutes to obtain an aluminum plate with an adhesive composition.
  • the adhesive composition after drying the MEK did not have adhesiveness at normal temperature (25°C).
  • the adhesive composition side of the aluminum plate with an adhesive composition was maintained at 180°C and on top of such was pressure fused a 10 mm x 40 mm area portion of a polycarbonate sheet (Iupilon manufactured by Mitsubishi Gas
  • Two aluminum plates with the adhesive composition were made to oppose each other so that the area of the overlapping portion on the adhesive composition side became a width of 25 mm and a length of 10 mm, between such was sandwiched a polycarbonate sheet (Iupilon manufactured by Mitsubishi Gas Chemical Company, Inc.) having a width of 25 mm, a length of 10 mm, and a thickness of 0.3 mm, pressure heating was performed at 180°C and 10 kg/cm 2 for 2 seconds, and the polycarbonate was melted and thereby fused to the aluminum plates.
  • the end portions of the aluminum plates not overlapping were sandwiched between the chucks of a tensile tester and the two aluminum plates were fractured by pulling apart at a pulling speed of 5 mm/min. The weight when fractured was measured and the shear strength was determined to be 200 to 300 kg/cm 2 .
  • reference numbers 1, 4 and 6 denote aluminum sheets
  • reference number 2 denote a polycarbonate sheet
  • reference number 3 denote chucks of the tensile tester
  • reference number 5 denote the adhesive composition

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)

Abstract

La présente invention a pour objet une pièce composite comprenant un métal et une matière plastique assemblés fermement, un précurseur de la pièce composite (précurseur de pièce composite), et un procédé de fabrication de la pièce composite, et une composition adhésive capable d'assembler fermement un métal et une matière plastique. La présente invention concerne également une pièce composite comprenant une résine d'uréthane ayant des accrochages avec la matière plastique et également avec un réseau époxy collé sur la surface de l'élément métallique, qui est obtenue par les étapes consistant à placer un élément métallique dans une filière de moulage et à injecter une matière plastique dans la filière de moulage et une composition adhésive comprenant un premier réseau polymère et un second réseau polymère, les premier et second réseaux polymères formant un réseau polymère interpénétrant.
PCT/US2011/029742 2010-03-30 2011-03-24 Pièce composite, précurseur de pièce composite et composition adhésive WO2011123321A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010-077600 2010-03-30
JP2010077600A JP2011207086A (ja) 2010-03-30 2010-03-30 複合部品、複合部品前駆体、及び接着剤

Publications (1)

Publication Number Publication Date
WO2011123321A1 true WO2011123321A1 (fr) 2011-10-06

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TW (1) TW201141673A (fr)
WO (1) WO2011123321A1 (fr)

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Publication number Priority date Publication date Assignee Title
CN102615775A (zh) * 2012-04-09 2012-08-01 昆山金利表面材料应用科技股份有限公司 一种带有塑料结构的金属件及其制作方法

Citations (6)

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Publication number Priority date Publication date Assignee Title
JPS58125773A (ja) 1981-11-02 1983-07-26 ダブリユー・アール・グレイス・アンド・カンパニー―コネチカット 有機樹脂組成物ならびにそれからなる熱活性接着剤および封緘剤
US4766183A (en) 1986-01-27 1988-08-23 Essex Specialty Products, Inc. Thermosetting composition for an interpenetrating polymer network system
US5194503A (en) 1992-07-07 1993-03-16 Basf Corporation Non-isocyanate flexibilizer for coatings
US5328940A (en) * 1992-07-20 1994-07-12 Lord Corporation Radiation-curable compositions containing hydroxy-terminated polyurethanes and an epoxy compound
EP0842995A1 (fr) * 1995-05-27 1998-05-20 Beiersdorf Aktiengesellschaft Adhésif thermoplastique
US6582824B1 (en) * 1998-10-02 2003-06-24 3M Innovative Properties Company Sealant composition, article and method

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Publication number Priority date Publication date Assignee Title
JPS58125773A (ja) 1981-11-02 1983-07-26 ダブリユー・アール・グレイス・アンド・カンパニー―コネチカット 有機樹脂組成物ならびにそれからなる熱活性接着剤および封緘剤
US4766183A (en) 1986-01-27 1988-08-23 Essex Specialty Products, Inc. Thermosetting composition for an interpenetrating polymer network system
US5194503A (en) 1992-07-07 1993-03-16 Basf Corporation Non-isocyanate flexibilizer for coatings
US5328940A (en) * 1992-07-20 1994-07-12 Lord Corporation Radiation-curable compositions containing hydroxy-terminated polyurethanes and an epoxy compound
EP0842995A1 (fr) * 1995-05-27 1998-05-20 Beiersdorf Aktiengesellschaft Adhésif thermoplastique
US6582824B1 (en) * 1998-10-02 2003-06-24 3M Innovative Properties Company Sealant composition, article and method

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHERN Y C ET AL: "INTERPENETRATING POLYMER NETWORKS OF POLYURETHANE CROSSLINKE EPOXY AND POLYURETHANES", CHEMICAL ABSTRACTS, CHEMICAL ABSTRACTS SERVICE (C A S), US, vol. 127, no. 13, 29 September 1997 (1997-09-29), pages 695, XP000648240, ISSN: 0009-2258 *

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JP2011207086A (ja) 2011-10-20

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