WO2009067112A1 - Compositions polymérisables par polymérisation cationique, induites par redox, à basse température de durcissement - Google Patents

Compositions polymérisables par polymérisation cationique, induites par redox, à basse température de durcissement Download PDF

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Publication number
WO2009067112A1
WO2009067112A1 PCT/US2007/085272 US2007085272W WO2009067112A1 WO 2009067112 A1 WO2009067112 A1 WO 2009067112A1 US 2007085272 W US2007085272 W US 2007085272W WO 2009067112 A1 WO2009067112 A1 WO 2009067112A1
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Prior art keywords
resin
cationically
polymeπzable
electron
vinyl
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PCT/US2007/085272
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English (en)
Inventor
Laxmisha M. Sridhar
Osama M. Musa
Original Assignee
Henkel Ag & Co. Kgaa
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Application filed by Henkel Ag & Co. Kgaa filed Critical Henkel Ag & Co. Kgaa
Priority to JP2010534925A priority Critical patent/JP5248623B2/ja
Priority to PCT/US2007/085272 priority patent/WO2009067112A1/fr
Priority to TW097119983A priority patent/TWI423998B/zh
Publication of WO2009067112A1 publication Critical patent/WO2009067112A1/fr
Priority to US12/777,351 priority patent/US8324319B2/en

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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
    • C08F4/00—Polymerisation catalysts
    • C08F4/40—Redox systems

Definitions

  • This invention relates to a redox-induced cationically polyme ⁇ zable composition that exhibits reduced cure temperature and to a method for reducing the cure temperature of a cationically polyme ⁇ zable composition.
  • processing speed leads to higher throughput and lower assembly costs
  • processing speed can be increased if the adhesive, coating, or encapsulant can be cured quickly at a relatively low curing temperature
  • a common mode of eiectronic packaging involves affixing semiconductor devices onto substrates by means of an adhesive or encapsulant.
  • the more prominent uses are the bonding of integrated circuit chips to metal lead frames or organic substrates, and the bonding of circuit packages or assemblies to printed wire boards, including, for example, die attach for array package, die attach for RFID package, and component attach for ink jet cartridge assembly.
  • low temperature cure assembly can minimize jetting trajectory distortion and improve printing quality
  • temperature-sensitive components or substrates such as, the paper-based antenna in RFID application and camera sensor in organic substrates
  • low temperature interconnect is very desirable
  • polyme ⁇ zable compositions that cure at low temperatures, preferably iess than 100 0 C
  • This invention is a polyme ⁇ zable composition
  • a polyme ⁇ zable composition comprising ( ⁇ ) a cationicaliy polyme ⁇ zable resin, ( ⁇ ) an onium salt, (in) an azo or peroxide initiator, and (iv) an electron-rich vinyl resin
  • this invention is a polyme ⁇ zable composition
  • a polyme ⁇ zable composition comprising (i) a cationicaiiy polymerizable resin, ( ⁇ ) an onium salt, (iii) an azo or peroxide initiator, and (iv) a catalytic or substoichiometric amount of an electron-rich vinyl resin
  • this invention is method for reducing the cure temperature of a cationicaiiy poSyme ⁇ zable resin, in which the cure of the resin is catalyzed by the addition of an onium salt and an azo or peroxide initiator to the resin, the method comprising adding an electron-rich vinyl resin to the mixture of resin, onium salt and azo or peroxide initiator
  • this invention is method for reducing the cure temperature of a cationicaiiy polymerizable resin, in which the cure of the resin is catalyzed by the addition of an onium salt and an azo or peroxide initiator to the resin, the method comprising adding a catalytic or substoichiometric amount of an eiectron-rich vinyl resin to the mixture of resin, onium salt and azo or peroxide initiator
  • a curable resin is one that is polyme ⁇ zable with or without crosslinking Curable and poiyme ⁇ zable are used interchangeably and a cationically curable resin or composition is one that is poiyme ⁇ zable Any cationically polyme ⁇ zable resin may be used in the above reaction
  • Exemplary cationically polymerizable resins include oxetanes, epoxies, spiroorthocarbonates, spiroorthoesters, and benzoxazines, or a mixture of any of those
  • Suitable oxetane resins are those disclosed in US patents 7,034,064, 6,982,338, 6,953,862, 6,943,258, 6,753,434, and those available from Toagosei Corporation under the tradenames OXT-221 , OXT-121 , OXT-101 , OXT-212, OXT-211 , CHOX 1 OX-SC, PNOX-1009, having the structures
  • Suitable epoxy resins include bisphenol epoxies, naphthalene epoxies, and aliphatic type epoxies
  • Commercially available materials include bisphenol type epoxy resins (for example, those sold under the tradenames EPICLON 830LVP, 830CRP, 835LV, 850CRP, available from Dainippon Ink & Chemicals, lnc ), naphthalene type epoxy resins (for example, those sold under the tradenames EPICLON HP4032, available from Dainippon Ink & Chemicals, lnc ), aliphatic epoxy resins (for example, those sold under the tradenames ARALDITE CYI 79, 184, 192, 175, 179, available from Ciba Specialty Chemicals, EPOXY 1234, 249, 206, available from Dow Corporation, and EHPE-3150, available from Daicel Chemical Industries, Ltd )
  • epoxy resins include cycloaliphatic epoxy resins, for example, 3,4- epoxy-cyciohexylmethyl 3,4-epoxycyclohexanecarboxylate , available as ERL-4221 from Union carbide and ARALDITE CY-179, available from Ciba-Geigy, diglycidylester of hexahydro-phthahc anhydride, available as CY-184 from Ciba-Geigy, b ⁇ s(3,4- epoxycyclohexylmethyl)-ad ⁇ pate, available as ERL-4229 from Union carbide, and other bisphenol-A type epoxy resins, bisphenol-F type epoxy resins, epoxy novolac resins, biphenyl type epoxy resins, naphthalene type epoxy resins, and dicyclopentadienephenol type epoxy resins, all commercially available from different sources
  • Exemplary spiroorthocarbonate and vinyl spiroorthocarbonates include those having the following structures
  • Exemplary electron-rich vinyl spirocarbonates include those having the following structures:
  • Exemplary spiroorthoesters include
  • Suitable benzoxazines include those compounds containing the structure
  • R and R are any organic moiety, including another benzoxazine structure
  • Exemplary benzoxazine compounds include those of the formulae
  • R 1 is a divalent radical that may be aliphatic, aromatic, or a combination of aliphatic and aromatic, and that may contain heteroatoms, such as oxygen, nitrogen, sulfur, phosphorous, or halogen, or that may be a single bond, or that may be S, S 2 , SO, SO 2 , O, or CO, and R 2 is hydrogen, an alkyl or substituted alkyl, an aromatic or substituted aromatic
  • the benzoxazine may also be present in a polymeric species, such as depicted in the following structure: which R 1 is as described above, ⁇ is an integer that will vary depending on the polymeric composition from which the benzoxazine depends, and each Q is a polymeric entity, for example, polyurethane, polyether, polyester, poly(butad ⁇ ene) or polystyre ⁇ ic
  • Exemplary onium salts include iodonium salts, sulfonium salts, diazonium salts, ammonium salts or a mixture of those salts
  • the onium salt is an
  • X is any suitable counter anion, for example, a halogen anion, CF 3 SO 3 , C 6 H 5 SO 3 ' , NO 3 " , AsF 6 " , SbF 6 " , FeCI 4 “ , SbCI 6 “ , BF 4 " , PF 6 “ , and (C 6 F 5 )B "
  • iodonium salts include (p-lsopropylphenyj)(p- methylphenyl) iodonium tetrak ⁇ s(pentafluorophenyl)borate from Gelest as RHODORSIL 2074, and bisdodecyl phenyliodonium hexafluoroantimonate as UV 9380 from General Electric
  • the onium salts are used in an effective amount In one embodiment, an effective amount is in the range of 0 1 to 10% by weight of the total resin
  • Exemplary azo initiators include, for example, azoisobutylonit ⁇ le, 2,2"- azobispropane, 2,2'-azobis(2-methylbutanenitnle), and m.m'-azoxystyrene
  • azo initiators are those available from Wako Specialty Company, such as those sold under the tradenames VA-044, VA-057, VA-085, V-70, VF-096, V-65, V-601 , V-59, V-40, VF-096, V-30, and those available from Akzo Nobel, such as those sold under the tradenames PERKADOX ACCN, PERKADOX AIBN 1 PERKADOX AMBN-GR, and those available from Dupont, such as those sold under the tradenames VAZO-52, VAZO-64, VAZO-67 and VAZO-88
  • the azo initiators are used in an effective amount In one embodiment an effective amount ranges from 0 1 to 10% by weight of the total resin
  • Exemplary peroxide initiators include those commercially available from Akzo Nobel, such as those sold under the tradenames PERKADOX and TRIGONOX Other peroxide initiators are suitable, provided they generate radicals with the vinyl resin for reaction with the onium salt
  • Exemplary peroxides include benzoyl peroxide, lauroyl peroxide, octanoyl peroxide, butyl peroctoate, dicumyl peroxide, acetyl peroxide, para- chlorobenzoyl peroxide and di-t-butyl diperphthalate
  • the peroxide initiators are used in an effective amount In one embodiment an effective amount ranges from 0 1 to 10% by weight of the total resin content
  • Exemplary electron-rich vinyl resins include vinyl ethers, spirocyctic vinyl ethers, styrenics (compounds containing a styrene moiety), cinnamyls (in this specification and claims compounds containing a cinnamyl moiety), N-v ⁇ nylam ⁇ des, and N-vinylamines
  • Suitable vinyl ether resins include, for example, poly(butad ⁇ enes), poly(carbonates), poiy(urethanes), poly(ethers), poly(esters), simple hydrocarbons, and simple hydrocarbons containing functionalities such as carbonyl, carboxyl, amide, carbamate, urea, ester, or ether, which also contain vinyl ether functionality
  • Suitable commercially available vinyl ether resins include cyclohexane-dimethanol divinylether, dodecylvinylether, cyclohexyl vinylether, 2-ethylhexyl vinylether, dipropyleneglycol divinylether, hexanediol divinylether, octadecylvinylether, and butandiol divinylether, available from International Specialty Products (ISP), vinyl ethers sold under the tradenames VECTOMER 4010, 4020, 4030, 4040, 4051 , 4210, 4220
  • Suitable spirocyciic vinyl ethers include, for example, those having the structures
  • Suitable styrenic resins include, for example, those disclosed in US patents 6,953,862, 6,908,969, 6,908,957, 6,809,155, 6,803,406, 6,716,992, 6,441 ,213, 6,441 ,121, 6,307,001 , 6,300,456, and those commercially available styrene, substituted styrenics, divinyl benzene, diphenylethylene, and any other resins possessing styrenic functionality (hereinafter styrenics) Such resins can be, for example, polyesters, carbamates, ureas Exemplary styrenic resins include compounds having the following structures in which R is an aliphatic or aromatic hydrocarbon, including those with heteroatoms.
  • Suitable cinnamyl resins include, for example, those disclosed in US patents 6,943,258, 6,753,434, 6,716,992, 6,908,969, 6,908,957, 6,809,155, 6,803,406, 6,753,434, 6,570,032, 6,441,121, 6,307,001 , 6,300,456
  • the cinnamyl compounds can be any small molecule, oligome ⁇ c, or polymeric material that contains a cinnamy! functionality
  • N-vinylamide resins include, for example, N-v ⁇ nyl- pyrrohdone, N-vinylformamide, and N-vinylcaprolactone
  • N-v ⁇ nylam ⁇ nes include, for example, N- vinylcarbazole, N-vinylpyrrole, N-vinylimidazole, and 2-methyl-N-v ⁇ nyl ⁇ midazole
  • this invention is a method for polymerizing a cationically polyme ⁇ zable composition of one or more cationically polyme ⁇ zable monomers comprising reacting the cationically polyme ⁇ zable composition in the presence of an onium salt, an azo or peroxide initiator, and an electron-rich vinyl resin
  • an onium salt reacting the cationically polyme ⁇ zable composition in the presence of an onium salt, an azo or peroxide initiator, and an electron-rich vinyl resin
  • this invention is a method for polymerizing a cationically poiyme ⁇ zable composition of one or more cationically polyme ⁇ zable monomers comprising reacting the cationically polyme ⁇ zable composition in the presence of an o ⁇ ium salt, an azo or peroxide initiator, and a catalytic or substoichiometric amount of an electron-rich vinyl resin
  • an o ⁇ ium salt an azo or peroxide initiator
  • a catalytic or substoichiometric amount of an electron-rich vinyl resin The components of such cationically polyme ⁇ zable composition are as described earlier in this specification
  • this invention is a method for lowering the cure temperature of a cationically polyme ⁇ zable composition
  • a cationically polyme ⁇ zable composition comprising one or more cationically polyme ⁇ zable monomers, an onium salt, and an azo or peroxide initiator, the method comprising adding to the cationically polyme ⁇ zable composition an electron-rich vinyl resin.
  • the components of such cationically polymerizable composition are as described earlier in this specification
  • this invention is a method for lowering the cure temperature of a cationicaliy polymerizable composition comprising one or more cationically polymerizable monomers, an onium salt, and an azo or peroxide initiator, the method comprising adding to the cationically polymerizable composition a catalytic or substoichiometric amount of an electron-rich vinyl resin
  • a catalytic or substoichiometric amount of an electron-rich vinyl resin The components of such cationically polymerizable composition are as described earlier in this specification.
  • this invention is a two-part cationicaiiy polymerizable composition, one part comprising cationically poiyme ⁇ zable monomer and an onium salt, and the second part comprising cationically poiyme ⁇ zable monomer and an azo or peroxide initiator Either the first part or the second part, or both, will contain an electron- rich vinyl resin.
  • the components of these parts have been described earlier in this specification The two parts may be mixed mechanically just before dispensing
  • this invention is a two-part cationically polymerizable composition, one part comprising cationically polymerizabie monomer and an onium salt, and the second part comprising cationically polyme ⁇ zable monomer and an azo or peroxide initiator
  • Either the first part or the second part, or both, will contain a catalytic or substoichiometric amount of an electron-rich vinyl resin
  • the components of these parts have been described earlier in this specification The two parts may be mixed mechanically just before dispensing.
  • the polymerization of one or more cationically polymenzable monomers in which the polymerization mix further comprises an onium salt, an azo or peroxide initiator, and an electron-rich vinyl resin, can be performed in the presence of one or more other vinyl monomers, such as, acrylates, methacrylat.es, maleimides, maleates, or fumarates, or a mixture of those ⁇ that is, vinyl monomers that are not typically denominated as electron-rich)
  • the azo or peroxide initiator will initiate the radical polymerization of these other vinyl monomers
  • the cationic polymerization of the cationic polyme ⁇ zable materials and the radical polymerization of these vinyl monomers can occur simultaneously or independently, depending on the choice of specific azo or peroxide initiator and the temperature at which the initiator decomposes and forms the initiating radical species In any case, the initiators can be chosen so that curing occurs at 100 D C or lower
  • the polymerization of one or more cationically polymenzable monomers, in which the polymerization mix further comprises an onium salt, an azo or peroxide initiator, and an electron-rich vinyl resin can be performed in the presence of a substoichiometric amount of one or more other vinyl monomers, such as, acrylates, methacrylates, maleimides, maleates, or fumarates, or a mixture of those
  • the cationic polymerization is initiated by a cationic macroinitiator generated by radical polymerization and followed by oxidation as shown in the below reaction scheme.
  • the electron-rich vinyl resin should be present in slight excess in comparison to the other vinyl resin.
  • This embodiment works well in a two part system, in which one part contains the cationically polymerizable resin and the second contains the electron-rich vinyl resin and the other vinyl resin.
  • Suitable acrylate and methacrylate resins include those having the generic
  • X 2 is an aromatic or aliphatic group.
  • exemplary X 2 entities include poly(butadienes), poly-(carbonates), poly(urethanes), poly(ethers), poly(esters), simple hydrocarbons, and simple hydrocarbons containing functionalities such as carbonyl, carboxyl, amide, carbamate, urea, ester, or ether.
  • Commercially available materials include butyl (meth)acrylate, isobutyl (meth)acryiate, 2-ethyi hexyl (meth)acrylate, isodecyl (meth)acrylate, n-laury!
  • the acrylate resins are selected from the group consisting of isobornyl acrylate, isobornyl methacrylate, lauryl acrylate, lauryl meth acrylate, poly(butadiene) with acrylate functionality and poly(butadiene) with methacrylate functionality.
  • Suitable maleitnide resins include those having the generic structure
  • X 1 is an aliphatic or aromatic group.
  • exemplary X 1 entities include, poly(butadienes), poly(carbonates), poly(urethanes), poly(ethers), poly(esters), simple hydrocarbons, and simple hydrocarbons containing functionalities such as carbonyl, carboxyl, amide, carbamate, urea, ester, or ether. These types of resins are commercially available and can be obtained, for example, from Dainippon Ink and Chemical, Inc.
  • Additional suitable maleimide resins include, but are not limited to, solid aromatic bismaleimide (BMI) resins, particularly those having the structure
  • Suitable bismaleimide resins having aromatic bridging groups are commercially available, and can be obtained, for example, from Sartomer (USA) or HOS-Technic GmbH (Austria).
  • maleimide resins include:
  • C 36 represents a linear or branched chain hydrocarbon chain (with or without cyclic moieties) of 36 carbon atoms;
  • Suitable fumarates and maleates include, for example, dioctyl maleate, dibutyl maieate, dioctyl fumarate, and dibutyi fumarate.
  • the cationically polymerizable composition may further comprise an additional monofu ⁇ ctional and/or polyfunctional cationicaily polymerizable resin, and/or a reactive cationically polymerizable diluent.
  • the cationically polymerizable composition may further comprise a filler.
  • suitable nonconductive fillers include alumina, aluminum hydroxide, silica, fused silica, fumed silica, vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, barium sulfate, zirconium, carbon black, organic fillers, and haiogenated ethylene polymers, such as, tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride.
  • suitable conductive fillers include carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, and alumina.
  • the filler particles may be of any appropriate size ranging from nano size to several mm. Appropriate filler sizes can be determined by the practitioner, but, in general, will be within the range of 20 nanometers to 100 microns. The choice of such size for any particular end use is within the expertise of one skilled in the art. Filler may be present in any effective amount, and typically, an effective amount will range from 10 to 90% by weight of the total composition. More than one filler type may be used in a composition and the fillers may or may not be surface treated.
  • the worklife of the composition can be lengthened by the addition of an epoxy resin or a radical inhibitor.
  • the epoxy resin will be present in an amount of 1 to 90% by weight of total resin.
  • Suitable epoxy resins are those previously disclosed in this specification.
  • the radical inhibitor will be present in an amount of 10ppm to 2000ppm.
  • Suitable radical inhibitors include, for example, hydroquinone, methylhydroqui ⁇ one, t- butylcatechol, phenothiazine, and NPAL having the structure
  • EXAMPLE 1 EFFECT OF ELECTRON-RICH VINYL COMPOUND ON CURE TEMPERATURE OF CATIONICALLY POLYMERIZABLE COMPOSITION
  • a cationically polymerizable composition was prepared as a control to contain oxetane (OXT-221) having the structure shown above in this specification, an iodonium salt (RHODORSIL-2074), and an azo initiator (VAZO-52). Additional compositions were prepared to contain the control composition and a catalytic amount of vinyl ether I, vinyl ether II, or a styrene compound, having the structures shown below. Samples of the compositions were cured and their peak temperature (Tpeak) recorded. Other samples of the same composition were stored at room temperature and gel times recorded to measure worklife.
  • OXT-221 oxetane
  • RHODORSIL-2074 iodonium salt
  • VAZO-52 azo initiator
  • Additional compositions were prepared to contain the control composition and a catalytic amount of vinyl ether I, vinyl ether II, or a styrene compound, having the structures shown below. Samples of the compositions were cured and their peak temperature (T
  • EXAMPLE 2 EFFECT OF EPOXY OR RADICAL INHIBITOR ON WORKLIFE OF CATIONICALLY POLYMERIZABLE COMPOSITION
  • epoxy or a radical inhibitor was added to the formulations.
  • a control cationically polymerizable composition was prepared to contain oxetane (OXT-221) having the structure shown above, an iodonium salt (RHODORSIL), an azo initiator (VAZO-52) and vinyl ether I or N having the structures shown above.
  • RHODORSIL iodonium salt
  • VAZO-52 azo initiator
  • vinyl ether I or N having the structures shown above.
  • epoxy resin or methyihydroquinone (MeHQ) as a radical inhibitor.
  • the epoxy resins used were a cycloaliphatic epoxy sold under the tradename CYRACURE UVR6128 from Dow chemicals or epoxy resin sold under the tradename EPON 834 from Hexion chemicals.
  • EXAMPLE 3 EFFECT OF PEROXIDE INITIATOR ON THE CURE TEMPERATURE OF CATIONICALLY POLYMERIZABLE COMPOSITIONS
  • Azo initiators can liberate N 2 gas upon decomposition, which is undesirable in applications where low outgassing is required.
  • the successful substitution of peroxides for the azo initiators will be dependent on the peroxide chosen.
  • Cationically polymerizable compositions were prepared as in the previous examples with the substitution of benzoyl peroxide and a commercial peroxide sold under the tradename TRIGONOX-23 for the azo initiators. The formulations of the compositions and the results are reported in TABLE 3. The data show that the (TRIGONOX) peroxide was more effective than benzoyl peroxide as an initiator.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract

L'invention concerne une composition polymérisable par polymérisation cationique comprenant (i) une résine polymérisable par polymérisation cationique, (ii) un sel d'onium, (iii) un initiateur peroxyde ou azoïque, qui présente une température de durcissement plus basse après addition au mélange réactionnel de (iv) une quantité catalytique ou inférieure à la quantité stoéchiométrique d'une résine vinylique riche en électrons.
PCT/US2007/085272 2007-11-20 2007-11-20 Compositions polymérisables par polymérisation cationique, induites par redox, à basse température de durcissement WO2009067112A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2010534925A JP5248623B2 (ja) 2007-11-20 2007-11-20 低い硬化温度を有するレドックス誘導カチオン重合性組成物
PCT/US2007/085272 WO2009067112A1 (fr) 2007-11-20 2007-11-20 Compositions polymérisables par polymérisation cationique, induites par redox, à basse température de durcissement
TW097119983A TWI423998B (zh) 2007-11-20 2008-05-30 具有低固化溫度之氧化還原－誘發之陽離子性可聚合組成物
US12/777,351 US8324319B2 (en) 2007-11-20 2010-05-11 Redox-induced cationically polymerizable compositions with low cure temperature

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PCT/US2007/085272 WO2009067112A1 (fr) 2007-11-20 2007-11-20 Compositions polymérisables par polymérisation cationique, induites par redox, à basse température de durcissement

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