US20030232926A1 - Thermoset adhesive films - Google Patents

Thermoset adhesive films Download PDF

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Publication number
US20030232926A1
US20030232926A1 US10/146,387 US14638702A US2003232926A1 US 20030232926 A1 US20030232926 A1 US 20030232926A1 US 14638702 A US14638702 A US 14638702A US 2003232926 A1 US2003232926 A1 US 2003232926A1
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United States
Prior art keywords
bis
maleimide
film adhesive
polymer
adhesive according
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Abandoned
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US10/146,387
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English (en)
Inventor
Nikola Nikolic
Ruzhi Zhang
Osama Musa
Hwail Jin
Bing Wu
David Shenfield
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National Starch and Chemical Investment Holding Corp
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National Starch and Chemical Investment Holding Corp
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Priority to US10/146,387 priority Critical patent/US20030232926A1/en
Assigned to NATIONAL STARCH AND CHEMICAL INVESTMENT HOLDING CORPORATION reassignment NATIONAL STARCH AND CHEMICAL INVESTMENT HOLDING CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MUSA, OSAMA M., NIKOLIC, NIKOLA A., ZHANG, RUZHI, JIN, HWAIL, SHENFIELD, DAVID, WU, BING
Priority to SG200302719A priority patent/SG108921A1/en
Priority to KR1020030029801A priority patent/KR20040030203A/ko
Priority to DE60303972T priority patent/DE60303972T2/de
Priority to JP2003132918A priority patent/JP4028431B2/ja
Priority to EP03009803A priority patent/EP1362901B1/en
Priority to TW092113003A priority patent/TWI296008B/zh
Publication of US20030232926A1 publication Critical patent/US20030232926A1/en
Priority to US11/044,374 priority patent/US20050137340A1/en
Priority to US11/248,490 priority patent/US7326754B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
    • C08F267/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00 on to polymers of amides or imides
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • 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
    • C09J109/00—Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
    • C09J109/02—Copolymers with acrylonitrile
    • 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
    • C09J125/00—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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/02—Homopolymers or copolymers of hydrocarbons
    • C09J125/04—Homopolymers or copolymers of styrene
    • C09J125/08—Copolymers of styrene
    • 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
    • C09J133/18—Homopolymers or copolymers of nitriles
    • C09J133/20—Homopolymers or copolymers of acrylonitrile
    • 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
    • C09J157/00—Adhesives based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J5/10—Joining materials by welding overlapping edges with an insertion of plastic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, 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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/414—Additional features of adhesives in the form of films or foils characterized by the presence of essential components presence of a copolymer
    • 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
    • C09J2425/00—Presence of styrenic polymer
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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
    • C09J2455/00—Presence of ABS

Definitions

  • This invention relates to film adhesives, and particularly film adhesives for use in semiconductor packaging
  • a common mode of electronics packaging involves affixing semiconductor devices onto substrates by means of an adhesive tape.
  • Epoxy compounds and resins currently are among the most commonly used materials for current film based adhesive applications, such as die attach, in which a semiconductor die is attached to a substrate.
  • a film-forming rubber polymer is blended with epoxy resins and a hardening agent. These compositions can then be cured upon application of heat, which results in the development of a thermoset network.
  • One drawback to epoxy adhesives is their ultimate latency. Typically, these materials must be stored at low temperature to avoid premature advancement of the adhesive. Moreover, the speed of cure for these compositions is relatively slow making the die-attach operation the least efficient step in the total assembly manufacturing process for wirebonded integrated circuit packages. This creates a need for a film adhesive that can be rapidly cured compared to the conventional thermoset film adhesives, and particularly to films containing no epoxy.
  • This invention is a film adhesive prepared from an adhesive composition comprising a polymer system, a film forming rubber compound, and curing agents for the polymeric system.
  • the polymer system contains no epoxy functionality.
  • the polymer system comprises a base polymer and electron donor and electron acceptor functionality.
  • the electron donor and electron acceptor functionality can be pendant from the base polymer, or can be interdispersed with the base polymer as independent compounds.
  • the base polymer can function as a film-forming rubber compound.
  • the film can be prepared directly as a monolayer from the adhesive composition, or from coating the adhesive composition onto both sides of a thermal resistant tape substrate.
  • the polymer system for preparing the film adhesives will contain a base polymer (hereinafter “polymer” or “base polymer”) and electron donor and electron acceptor functionality.
  • the system can be segregated into several classes: (1) an unsubstituted base polymer blended with an independent electron donor compound and an independent electron acceptor compound; (2) a base polymer substituted with pendant electron acceptor functionality, blended with an independent electron donor compound, and optionally an independent electron acceptor compound; (3) a base polymer substituted with pendant electron donor functionality, blended with an independent electron acceptor compound and optionally an independent electron donor compound; (4) a base polymer substituted with pendant electron donor and electron acceptor functionality, or a combination of a base polymer substituted with pendant electron donor functionality and a base polymer substituted with pendant electron acceptor functionality, optionally blended with an independent electron donor compound, or an independent electron acceptor compound, or both.
  • the molar ratio can range from 0.01-1.0:1.0-0.01.
  • a suitable base polymer in the polymer system of the inventive film adhesive is prepared from acrylic and/or vinyl monomers using standard polymerization techniques.
  • the acrylic monomers that may be used to form the base polymer include ⁇ , ⁇ -unsaturated mono and dicarboxylic acids having three to five carbon atoms and acrylate ester monomers (alkyl esters of acrylic and methacrylic acid in which the alkyl groups contain one to fourteen carbon atoms). Examples are methyl acryate, methyl methacrylate, n-octyl acrylate, n-nonyl methacrylate, and their corresponding branched isomers, such as, 2-ethylhexyl acrylate.
  • the vinyl monomers that may be used to form the base polymer include vinyl esters, vinyl ethers, vinyl halides, vinylidene halides, and nitriles of ethylenically unsaturated hydrocarbons. Examples are vinyl acetate, acrylamide, 1-octyl acrylamide, acrylic acid, vinyl ethyl ether, vinyl chloride, vinylidene chloride, acrylonitrile, maleic anhydride, and styrene.
  • Another suitable base polymer in the polymer system of the inventive film adhesive is prepared from conjugated diene and/or vinyl monomers using standard polymerization techniques.
  • the conjugated diene monomers that may be used to form the polymer base include butadiene-1,3, 2-chlorobutadiene-1,3, isoprene, piperylene and conjugated hexadienes.
  • the vinyl monomers that may be used to form the base polymer include styrene, ⁇ -methylstyrene, divinylbenzene, vinyl chloride, vinyl acetate, vinylidene chloride, methyl methacrylate, ethyl acrylate, vinylpyridine, acrylonitrile, methacrylonitrile, methacrylic acid, itaconic acid and acrylic acid.
  • the base polymer can be purchased commercially.
  • Suitable commercially available polymers include acrylonitrile-butadiene rubbers from Zeon Chemicals and styrene-acrylic copolymers from Johnson Polymer.
  • the degree of substitution can be varied to suit the specific requirements for cross-link density in the final applications. Suitable substitution levels range from 6 to 500, preferably from 10 to 200.
  • the base polymer whether substituted or unsubstituted will have a molecular weight range of 2,000 to 1,000,000.
  • the glass transition temperature (Tg) will vary depending on the specific base polymer.
  • Tg for butadiene polymers ranges from ⁇ 100° C. to 25° C.
  • modified acrylic polymers from 15° C. to 50° C.
  • Suitable electron donor functionality includes vinyl ether groups, vinyl silane groups, and carbon to carbon double bonds external to an aromatic ring and conjugated with the unsaturation in the aromatic ring.
  • Suitable electron acceptor groups include maleimides, acrylates, fumarates and maleates.
  • Examples of suitable starting materials for reacting with complementary functionality on the base polymer in order to add the electron donor or electron acceptor functionality pendant to the base polymer include: for electron donor functionality, hydroxybutyl vinyl ether, cinnamyl alcohol, 1,4-cyclohexane-dimethanol monovinyl eether, 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate, isoeugenol, and the derivatives of the aforementioned compounds; for electron acceptor functionality, dioctyl maleate, dibutyl maleate, dioctyl fumarate, dibutyl fumarate, N-(6-hydroxyhexyl) maleimide, 6-maleimidocaproic acid, and 3-maleimidopropionic acid.
  • Independent electron donor compounds for blending with the base polymer include compounds having at least two vinyl ether groups, or having at least two carbon to carbon double bonds external to aromatic rings and conjugated with the unsaturation in the aromatic ring.
  • Suitable divinyl ether examples include compounds such as bis[4-(vinyloxy)butyl]terephthalate, bis[4-(vinyloxy)butyl] (4-methyl-1,3-phenylene)biscarbamate, bis[4-(vinyloxy) butyl] 1,6-hexanediylbiscarbamate, 4-(vinyloxy)butyl stearate, and bis[4-(vinyloxy)butyl] (methylenedi-4,1-phenylene)biscarbamate (sold under the trade name Vectomer from Morflex, Inc).
  • Exemplary compounds having at least two carbon to carbon double bonds external to aromatic rings and conjugated with the unsaturation in the aromatic ring include:
  • Independent electron acceptor compounds for blending with the base polymer include resins having at least two intramolecular maleimide, acrylate, fumarate or maleate groups.
  • bismaleimides include: N,N′-ethylene-bis-maleimide, N,N′-butylene-bis-maleimide, N,N′-phenylene-bis-maleimide, N,N′-hexamethylene-bis-maleimide, N,N′-4,4′-diphenyl methane-bis-maleimide, N,N′-4,4′-diphenyl ether-bis-maleimide, N,N′-4,4′-diphenyl sulfone-bis-maleimide, N,N′-4,4′-dicyclohexyl methane-bis-maleimide, N,N′-xylylene-bis-maleimide, N,N′-diphenyl cyclohexane-bis-maleimide and the like.
  • Suitable film forming resins or compounds include acrylic polymers (sold under the trade name TEISAN RESIN from Nagase ChemteX Corporation) and acrylonitrile-butadiene elastomers (sold under the trade name NIPOL from Zeon Chemicals). These materials, in general, will be present in the adhesive composition from which the film will be prepared, in an amount ranging from 10% to 70%, preferably 15% to 50%, by weight of the adhesive formulation. Other levels may be suitable depending on the end use application, and optimal levels can be determined without undue experimentation on the part of the formulator.
  • Suitable curing agents for the polymer system are thermal initiators and photoinitiators, present in an amount of 0.1% to 10%, preferably 0.1% to 5.0%, by weight of the polymer system.
  • Preferred thermal initiators include peroxides, such as butyl peroctoates and dicumyl peroxide, and azo compounds, such as 2,2′-azobis(2-methyl-propanenitrile) and 2,2′-azobis(2-methyl-butanenitrile).
  • a preferred series of photoinitiators is one sold under the trademark Irgacure by Ciba Specialty Chemicals.
  • both thermal initiation and photoinitiation may be desirable; for example, the curing process can be started by irradiation, and in a later processing step curing can be completed by the application of heat to accomplish the thermal cure.
  • these compositions will cure within a temperature range of 70° C. to 250° C., and curing will be effected at a temperature within the range of ten seconds to three hours.
  • the time and temperature curing profile of each formulation will vary with the specific electron donor compound and the other components of the formulation, but the parameters of a curing profile can be determined by a practitioner skilled in the art without undue experimentation.
  • Suitable epoxy compounds or resins include bifunctional and polyfunctional epoxy resins such as bisphenol A-type epoxy, cresol novolak epoxy, or phenol novolak epoxy.
  • Another suitable epoxy resin is a multifunctional epoxy resin from Dainippon Ink and Chemicals, Inc. (sold under the product number HP-7200). When added to the formulation, the epoxy will be present in an amount up to 80% by weight.
  • Suitable curing agents include amines, polyamides, acid anhydrides, polysulfides, trifluoroboron, and bisphenol A, bisphenol F and bisphenol S, which are compounds having at least two phenolic hydroxyl groups in one molecule.
  • a curing accelerator may also be used in combination with the curing agent.
  • Suitable curing accelerators include imidazoles, such as 2-methylimidazole, 2-ethyl-4-methylimidazole, 4-methyl-2-phenylimidazole, and 1-cyanoethyl-2-phenylimidazolium trimellitate.
  • the curing agents and accelerators are used in standard amounts known to those skilled in the art.
  • adhesion promoters epoxides, silanes
  • dyes epoxides, silanes
  • rheology modifiers epoxides, silanes
  • materials and the amounts needed are within the expertise of those skilled in the art.
  • Filler particles that enhance the mechanical, electrical conductivity, or thermal conductivity may also be added.
  • Suitable conductive fillers are carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, and alumina.
  • Suitable nonconductive fillers are particles of vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, fused silica, fumed silica, barium sulfate, and halogenated ethylene polymers, such as tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride.
  • fillers will be in amounts of 0.1% to 90%, preferably from 5% to 90%, by weight of the formulation.
  • This example discloses a butadiene/acrylonitrile base polymer containing pendant acrylate (electron acceptor) functionality.
  • Carboxylated butadiene/acrylonitrile polymer (50.6 g) (Nipol 1072 from Zeon Chemicals) was solvated in 4-methyl-2-pentanone (MIBK, 250 mL) in a 500 mL four-necked flask equipped with a mechanical stirrer, condenser and drying tube.
  • MIBK 4-methyl-2-pentanone
  • Glycidyl methacrylate (9.78 g) and tetrabutylphosphonium acetate solution (0.58 g) (TBPAAC, catalyst, 70% by weight of tetrabutylphosphonium acid acetate in methanol from Morton International, Inc.) were added to the mixture with stirring. The mixture was heated to 110° C. and held at that temperature for approximately twelve hours.
  • the final product has a viscosity of 4870 mPa.s at ambient temperature and according to titration results of the residual carboxylic acid of the modified Nipol rubber, the carboxyl conversion is about 90%.
  • the weight average molecular weight and the number average molecular weight of the modified Nipol polymer are 430,500 g/mol and 60,900 g/mol, respectively.
  • This example discloses a butadiene/acrylonitrile base polymer with pendant styrenic (electron donor) functionality
  • Carboxylated butadiene/acrylonitrile polymer (38.0 g) (Nipol 1072 from Zeon Chemicals) was solvated in 4-methyl-2-pentanone (MIBK, 255 mL) in a 500 mL four-necked flask equipped with a mechanical stirrer, condenser and drying tube. Isoeugenol glycidyl ether (11.43 g) and tetrabutylphosphonium acetate solution (0.62 g) (TBPAAC, catalyst, 70% by wetight of tetrabutylphosphonium acid acetate in methanol from Morton International, Inc.) were added into the mixture with stirring. The mixture was heated to 110° C.
  • the carboxyl conversion is about 87%.
  • the product was purified by precipitation in methanol three times. According to GPC analysis, the weight average molecular weight and the number average molecular weight of the modified Nipol polymer are 554,400 g/mol and 89,100 g/mol, respectively.
  • This example discloses a butadiene/acrylonitrile base polymer with pendant styrenic (electron donor) functionality
  • Carboxylated butadiene/acrylonitrile polymer (53.8 g) (Nipol 1072 from Zeon Chemicals) was solvated in 4-methyl-2-pentanone (MIBK, 360 mL) in a 1 L four-necked flask equipped with a mechanical stirrer, condenser and drying tube.
  • MIBK 4-methyl-2-pentanone
  • Glycidyl N-(3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl) carbamate (14.8 g)
  • tetrabutylphosphonium acetate solution (0.54 g) (TBPAAC, catalyst) were added into the mixture with stirring. The mixture was heated to 105° C. and held at that temperature for approximately fifteen hours.
  • the final product has a viscosity of 2000 mPa.s at ambient temperature and according to titration results, the carboxyl conversion is about 88%.
  • the weight average molecular weight and the number average molecular weight of the modified Nipol polymer are 666,000 g/mol and 75,600 g/mol, respectively.
  • This example discloses a butadiene/acrylonitrile base polymer with pendant cinnamyl (electron donor) functionality
  • This example discloses a butadiene/acrylonitrile base polymer with pendant cinnamyl (electron donor) functionality
  • This example discloses a butadiene/acrylonitrile base polymer with pendant styrenic (electron donor) functionality
  • This example discloses a butadiene/acrylonitrile base polymer with pendant styrenic (electron donor) functionality
  • This example discloses a butadiene/acrylonitrile base polymer with pendant vinyl ether (electron donor) functionality
  • This example discloses a butadiene/acrylonitrile base polymer with pendant vinyl ether (electron donor) functionality
  • This example discloses a hydroxylated styrene/butadiene base polymer with pendant styrenic (electron donor) functionality
  • hydroxylated styrene/butadiene polymer is solvated in dry toluene at 90° C. under nitrogen, followed by the addition of one molar equivalent of 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate (m-TMI) together with 0.07% of dibutyltin dilaurate (catalyst) based on the total amount of reactants.
  • m-TMI 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate
  • catalyst dibutyltin dilaurate
  • This example discloses a hydroxylated styrene/butadiene base polymer having pendant styrenic (electron donor) functionality
  • hydroxylated styrene/butadiene polymer prepared as above is solvated in dry toluene at 90° C. under nitrogen, followed by the addition of one molar equivalent of 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate (m-TMI) together with 0.07% of dibutyltin dilaurate (catalyst) based on the total amount of reactants.
  • m-TMI 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate
  • catalyst dibutyltin dilaurate
  • This example discloses a hydroxylated styrene/butadiene base polymer having pendant maleimide (electron acceptor) functionality
  • This example discloses a polybutadiene base polymer with pendant styrenic (electron donor) functionality
  • This example discloses a styrene/acrylic base polymer with pendant acrylate (electron acceptor) functionality.
  • This example discloses a styrene/acrylic base polymer with pendant styrenic (electron donor) functionality
  • the weight average molecular weight and the number average molecular weight of the modified styrene-acrylic polymer are 15,600 g/mol and 8,400 g/mol, respectively.
  • the glass transition temperature of the modified styrene-acrylic polymer is approximately 40° C.
  • An adhesive film was prepared from a polymer system comprising an unsubstituted acrylic/rubber base polymer, an independent electron acceptor resin, an independent electron donor resin, and an epoxy resin, which components and parts by weight used are identified in Table 1.
  • the film formulation also contained a radical initiator, hardeners for the epoxy, a filler and adhesion promoters. TABLE 1 Component Chemical Class Parts or Function Source by wt. Base polymer SG-80DR 5 Acrylic rubber Nagase ChemteX Corp.
  • the electron donor had the following structure:
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • An adhesive film was prepared from a polymer system comprising a poly(butadiene) base polymer substituted with pendant electron acceptor functionality, an independent electron acceptor resin, an independent electron donor resin, and an epoxy resin, which components and parts by weight used are identified in Table 2.
  • the film formulation also contained a radical initiator, hardeners for the epoxy, and adhesion promoters. TABLE 2 Component Chemical Class Parts or Function Source by wt. Butadiene base polymer Polymer from Example 1.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • An adhesive film was prepared from a polymer system comprising a styrene/acrylic base polymer substituted with pendant electron donor functionality, an independent electron acceptor resin, an independent electron donor resin, and an acrylonitrile/butadiene rubber, which components and parts by weight used are identified in Table 3.
  • the film formulation also contained a radical initiator and adhesion promoters. TABLE 3 Component Chemical Class Parts or Function Source by wt.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • An adhesive film was prepared from a polymer system comprising a styrene/acrylic base polymer substituted with pendant electron donor functionality, an acrylonitrile/butadiene base polymer substituted with pendant electron donor functionality, an independent electron acceptor resin, an independent electron donor resin, which components and parts by weight used are identified in Table 4.
  • the film formulation also contained a radical initiator, filler, and adhesion promoters. TABLE 4 Component Chemical Class Parts or Function Source by wt.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • An adhesive film was prepared from a polymer system comprising a acrylonitrile/butadiene base polymer substituted with pendant electron donor functionality, an independent electron acceptor resin, an independent electron donor resin, and an epoxy, which components and parts by weight used are identified in Table 5.
  • the film formulation also contained a radical initiator, hardeners for the epoxy, filler, and adhesion promoters. TABLE 5 Component Chemical Class Parts or Function Source by wt.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • An adhesive film was prepared from a polymer system comprising a acrylonitrile/butadiene base polymer substituted with pendant electron donor functionality, an independent electron acceptor resin, an independent electron donor resin, and an epoxy, which components and parts by weight used are identified in Table 6.
  • the film formulation also contained a radical initiator, hardeners for the epoxy, filler, and adhesion promoters. TABLE 6 Component Chemical Class Parts or Function Source by wt.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • An adhesive film was prepared from a polymer system comprising an acrylonitrile/butadiene base polymer substituted with pendant electron acceptor functionality, a styrene/acrylic base polymer substituted with pendant electron donor functionality, an independent electron acceptor resin, an independent electron donor resin, which components and parts by weight used are identified in Table 7.
  • the film formulation also contained a radical initiator. TABLE 7 Component Chemical Class Parts or Function Source by wt.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.
  • This example discloses an adhesive film prepared with a polymeric system containing an acrylonitrile/butadiene base polymer, and epoxy resin, and no electron donor nor electron acceptor functionality.
  • the formulation also contained a phenol novolak resin and curing agents.
  • the formulation components and parts by weight are disclosed in Table 8. TABLE 8 Component Chemical Class Parts or Function Source by wt. Acrylonitrile/butadiene Nipol 1072 2.7 rubber Zeon Chemicals Epoxy HP-7200H 3.5 Dainippon Ink and Chemicals, Inc. Phenol Novolak resin HRJ-1166 1 Schenectady International Inc.
  • the film formulation was prepared by mixing the components in methyl ethyl ketone with stirring, followed by vacuum degassing.
  • the varnish obtained was coated to a thickness of 2 mil onto a 5 mil thick silicone-treated release-liner and then dried by heating at 100° C. for 10 minutes to form a partially cured adhesive film with a thickness of 1 mil.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesive Tapes (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
US10/146,387 2002-05-14 2002-05-14 Thermoset adhesive films Abandoned US20030232926A1 (en)

Priority Applications (9)

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US10/146,387 US20030232926A1 (en) 2002-05-14 2002-05-14 Thermoset adhesive films
SG200302719A SG108921A1 (en) 2002-05-14 2003-05-09 Thermoset adhesive films
TW092113003A TWI296008B (en) 2002-05-14 2003-05-12 Thermoset adhesive films
JP2003132918A JP4028431B2 (ja) 2002-05-14 2003-05-12 熱硬化性接着フィルム
DE60303972T DE60303972T2 (de) 2002-05-14 2003-05-12 Wärmehärtbare Klebefilme
KR1020030029801A KR20040030203A (ko) 2002-05-14 2003-05-12 열경화성 접착 필름
EP03009803A EP1362901B1 (en) 2002-05-14 2003-05-12 Thermoset adhesive films
US11/044,374 US20050137340A1 (en) 2002-05-14 2005-01-27 Thermoset adhesive films
US11/248,490 US7326754B2 (en) 2002-05-14 2005-10-12 Thermoset adhesive films

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US11/044,374 Abandoned US20050137340A1 (en) 2002-05-14 2005-01-27 Thermoset adhesive films
US11/248,490 Expired - Fee Related US7326754B2 (en) 2002-05-14 2005-10-12 Thermoset adhesive films

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KR (1) KR20040030203A (enrdf_load_stackoverflow)
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US20070123642A1 (en) * 2005-11-30 2007-05-31 Xerox Corporation Phase change inks containing curable isocyanate-derived compounds
US20070120909A1 (en) * 2005-11-30 2007-05-31 Xerox Corporation Phase change inks containing curable isocyanate-derived compounds and phase change inducing components

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US8287686B2 (en) 2006-07-24 2012-10-16 Designer Molecules, Inc. Derivatives of poly(styrene-co-allyl alcohol) and methods for use thereof
WO2008128209A1 (en) * 2007-04-12 2008-10-23 Designer Molecules, Inc. Polyfunctional epoxy oligomers
ATE547446T1 (de) * 2007-05-16 2012-03-15 Dow Global Technologies Llc Flammenhemmende zusammensetzungen
WO2009070172A1 (en) * 2007-11-30 2009-06-04 Henkel Ag & Co. Kgaa Curable resins containing acetal, ketal, acetal ester, or ketal ester linkages
US8308892B2 (en) 2008-04-09 2012-11-13 Designer Molecules, Inc. Di-cinnamyl compounds and methods for use thereof
US8217120B2 (en) * 2008-08-13 2012-07-10 Designer Molecules, Inc. Functionalized styrene oligomers and polymers
US8008419B2 (en) 2008-08-13 2011-08-30 Designer Molecules, Inc. Siloxane monomers and methods for use thereof
US8158748B2 (en) * 2008-08-13 2012-04-17 Designer Molecules, Inc. Hetero-functional compounds and methods for use thereof
US9441123B2 (en) 2012-08-15 2016-09-13 Penn Color, Inc. Cationic water based polymers for ink, coating, and film applications
US9434849B2 (en) 2012-10-19 2016-09-06 Penn Color, Inc. Water based anionic polymers for ink, coating, and film applications
US11247424B1 (en) 2016-12-13 2022-02-15 Bridgestone Americas Tire Operations, Llc Methods for retreading tires
JP7093150B2 (ja) * 2018-12-06 2022-06-29 日本化薬株式会社 硬化性樹脂組成物及びその硬化物
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EP1362901A2 (en) 2003-11-19
EP1362901A3 (en) 2004-05-26
US20060030672A1 (en) 2006-02-09
TWI296008B (en) 2008-04-21
JP4028431B2 (ja) 2007-12-26
SG108921A1 (en) 2005-02-28
DE60303972T2 (de) 2006-09-07
EP1362901B1 (en) 2006-03-15
US7326754B2 (en) 2008-02-05
DE60303972D1 (de) 2006-05-11
KR20040030203A (ko) 2004-04-09
JP2004161990A (ja) 2004-06-10
US20050137340A1 (en) 2005-06-23
TW200406477A (en) 2004-05-01

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