WO2009136920A1 - Nitrones multifonctionnelles dans des systèmes non radicalaires - Google Patents

Nitrones multifonctionnelles dans des systèmes non radicalaires Download PDF

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Publication number
WO2009136920A1
WO2009136920A1 PCT/US2008/062904 US2008062904W WO2009136920A1 WO 2009136920 A1 WO2009136920 A1 WO 2009136920A1 US 2008062904 W US2008062904 W US 2008062904W WO 2009136920 A1 WO2009136920 A1 WO 2009136920A1
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WO
WIPO (PCT)
Prior art keywords
nitrone
acrylate
epoxy
cyanate ester
nltrone
Prior art date
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PCT/US2008/062904
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English (en)
Inventor
Osama M. Musa
Laxmisha M. Sridhar
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Henkel Corporation
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Publication date
Application filed by Henkel Corporation filed Critical Henkel Corporation
Priority to PCT/US2008/062904 priority Critical patent/WO2009136920A1/fr
Priority to TW097120662A priority patent/TW200946560A/zh
Publication of WO2009136920A1 publication Critical patent/WO2009136920A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/32—Compounds containing nitrogen bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59

Definitions

  • This invention relates to the use of nitro ⁇ es in the cure of non-raclica! mediated organic chemistry systems, and in particular in the cure of formulations for adhesives, coatings, and encapsulants.
  • the adhesives, coatings, and encapsulants are used in electronic applications.
  • Radical cure has the disadvantages of oxygen sensitivity before and during cure, and significant shrinkage after cure, creating a need for a chemistry that avoids these problems.
  • This invention is a curable composition
  • a multifunctional nitrone and another compound for purposes of this specification and the claims, compound is deemed to include monomers, oligomers, and polymers. Such compounds include acrylates, maleimides, cyanate esters, and epoxies The nitrone undergoes crosslinking with the other compound through cycloaddition or ring opening initiated by the nitrone dipole without the sensitivity to oxygen experienced by free radical curing or crosslinking.
  • Nitrone chemistry can provide a wide range of curing temperatures in curable compositions comprising a nitrone and one or more other compounds.
  • the curing temperature will depend on the particular compound Within the electronics packaging industry, lower cure temperatures would be useful, for example, in die attach operations (silicone dies attached to substrates), underfill operations (encapsulation of solder electrical connections within an electronic package ⁇ , and dual cure operations (B-staging one chemistry at a lower temperature than the curing temperature); higher cure temperatures would be useful, for example, in those applications where the curable composition is used in place of a metallic solder.
  • Figure 1 depicts a semiconductor die on an array and metal leadframe showing the placement of a die attach adhesive.
  • Figure 2 depicts a flip-chip semiconductor electrically joined to a substrate with solder and underfilled with an encapsulant composition.
  • Nitrones are 1 ,3-dipolar species prepared through an easy one step, room temperature condensation reaction between an aldehyde and an alkylhydroxylamine as depicted here:
  • Nitrones are known to participate in 1 ,3-d ⁇ polar cycloaddition reactions with dipoiarophiles (2 ⁇ -partners) to give cycloadducts.
  • the cycloaddition reaction is insensitive to oxygen and moisture and generates a five-membered ring called an isoxazohdine:
  • Nitrones also can initiate polymerization of heterocyclic monomers, such as epoxies, by ring opening: I ⁇ Polymer
  • Exemplary compounds that are suitable for cure with nitrones include, but are not limited to, those compounds that contain functionality reactive with nitrone groups, such as, epoxy, acrylate (which includes methacrylate), maleimide (which includes multifunctional compounds, such as bis- and tris-maleimides), cyanate ester, and vinyl (such as in vinyl ethers and styrenes)
  • Those functionalities can be appended to a wide variety of compounds, such as polyesters, poly(butadienes), siliconized olefins, silicone resins, siloxanes, and other such materials.
  • the compounds are selected from the group consisting of epoxies, acryiates, maleimides, and cyanate esters.
  • ⁇ O O j n which X is an aromatic group.
  • Bismaleimide resins having these X bridging groups are commercially available, and can be obtained, for example, from Sartomer (USA) or HOS-Technic GmbH (Austria).
  • 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, or ether. These types of compounds are commercially available and can be obtained, for example, from National Starch and Chemical Company and Dainippon Ink and Chemical, Inc. [0013] Specific preferred maleimides
  • C 36 represents a linear or branched chain (with or without cyclic moieties) of 36 carbon atoms
  • Suitable acrylates for use in formulation with the inventive compounds include
  • X 2 is an aromatic or aliphatic group
  • Exemplary X 2 groups include poly(butadienes), poiy(carbonates), poly(urethanes), poly ⁇ ethers), poly(esters), simple hydrocarbons, and simple hydrocarbons containing functionalities such as carbonyl, carboxyi, amide, carbamate, urea, or ether
  • Commercially available materials include butyl (meth)acrylate, isobutyl (meth)acrylate, 2-ethyl hexyl (meth)acrylate, isodecyl (meth)acrylate, n-lauryl (meth)acrylate, alkyl (meth)acrylate, tridecyl (meth)acrylate, n-stearyl (meth)acrylate, cyclohexyl(meth)acrylate, tetrahydro-furfuryl(meth)acryiate, 2-
  • Suitable epoxies for use in compositions with the nitrones include bisphenol, naphthalene, and aliphatic type epoxies
  • Commercially available materials include bisphenol type epoxy resins (Epiclon 830LVP, 830CRP, 835LV, 850CRP) available from Dainippon Ink & Chemicals, Inc , naphthalene type epoxy (Epiclon HP4032) available from Dainippon Ink & Chemicals, Inc ; aliphatic epoxy resins (AraJdite CY179, 184, 192, 175, 179) available from Ciba Specialty Chemicals, (Epoxy 1234, 249, 206) available from Union Carbide Corporation, and (EHPE-3150) available from Daicel Chemical Industries, Ltd
  • Other suitable epoxy resins include cycloaliphatic epoxy resins, bisphenol-A type epoxy resins, bisphenol-F type epoxy resins (e g RSL 1739 from Hexion Specialty Chemical
  • Suitable cyanate esters for use m compositions with the nitrones include those
  • N E CC-O-1 — ) having the generic structure ⁇ 'n tn which n is 1 or larger, and X 7 is a hydrocarbon group
  • X 7 entities include bisphenol, phenol or cresol novolac, dicyclopentadiene, polybutadiene, polycarbonate, polyurethane, pofyether, or polyester
  • Commercially available materials include, AroCy L-10, AroCy XU366, AroCy XU371 , AroCy XU378, XU71787 02L, and XU 71787 07L, available from Huntsman LLC, P ⁇ maset PT30, P ⁇ maset PT30 S75, P ⁇ maset PT60, P ⁇ maset PT60S, P ⁇ maset BADCY, P ⁇ maset DA230S, P ⁇ maset MethylCy, and P ⁇ maset LECY, available from Lonza Group Limited, 2-allyphenoi cyanate
  • Suitable vinyl ethers for use in compositions with the nitrones include those having
  • X 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, or ether.
  • resins include cyclohenanedimethanol divinylether, dodecylvi ⁇ ylether, cyclohexyl vinylether, 2-ethylhexyl vinylether, dipropyleneglycol divinylether, hexanediol divinylether, octadecylvi ⁇ ylether, and butandiol divinylether available from International Speciality Products (ISP); Vectomer 4010, 4020, 4030, 4040, 4051 , 4210, 4220, 4230, 4060, 5015 available from Sigma-Aldrich, lnc
  • Suitable poly(butadienes) for use in compositions with the nitrones include poly ⁇ butad ⁇ enes), epoxidized poly(butad ⁇ enes), maleic poly(butadienes), acryiated poly(butadienes), butadiene-styre ⁇ e copolymers, and butadiene-acrylomtrile copolymers.
  • Suitable siliconized olefins for use in the compositions with the nitrones are obtained by the selective hydrosilation reaction of silicone and divinyl materials, having the generic structure,
  • n-i is 2 or more, n 2 is 1 or more and n ! >n 2 .
  • Suitable silicones for use in compositions with the nitrones include reactive silicone resins having the generic structure in which ⁇ is 0 or any integer, X 4 and X 5 are hydrogen, methyl, amine, epoxy, carboxyl, hydroxy acrylate methacrylate, mercapto, phenol, or vinyl functional groups R 2 and R 3 can be -H, -CH 3 , vinyl phenyl, or any hydrocarbon structure with more than two carbons
  • Commercially available materials include KF8012, KF8002, KF8003, KF-1001 , X-22-3710, KF6001 X-22-164C, KF2001 , X- 22-170DX, X-22-173DX, X-22-174DX X-22-176DX KF-857 KF862, KF8001 , X-22-3367, and X-22-3939A available from Shin-Etsu Silicone International Trading (Shanghai) Co , Ltd
  • Suitable styrenic compounds for use in compositions with the nitrones include
  • X 3 entities include poly(butad ⁇ enes) polycarbonates), poly(urethanes), poly(ethers) poly(esters), simple hydrocarbons and simple hydrocarbons containing functionalities such as carbonyl, carboxyl, amide, carbamate urea, or ether These resins are commercially available and can be obtained, for example, from National Starch and Chemical Company or Sigma-Ald ⁇ ch Co
  • one or more fillers or spacers, or both may be added to the curable composition and usually are added for improved Theological properties, stress reduction, and bondline control
  • suitable ⁇ onconductive fillers include alumina, aluminum hydroxide, silica, vermicuiite, mica, wollastonite, calcium carbonate titania, sand, glass, barium sulfate, zirconium, carbon black, organic fillers, and organic polymers including but not limited to halogenated 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 particles may be of any appropriate size ranging from nano size to several mm, depending on whether they are used as fillers or spacer
  • Nitrone B may be prepared according to the same procedure for the synthesis of Nitrone A except that 1 ,3-be ⁇ zenedialdehyde will be used instead of 1 ,4-benzened ⁇ aldehyde.
  • EXAMPLE 3 SYNTHESIS OF NITRONE C
  • the starting dialdehyde was first prepared according to the following reaction scheme:
  • Nitrone C was prepared from the diaidehyde according to the following reaction scheme:
  • Nitrone D was prepared according to the following reaction scheme starting from 4- hydroxybenzaldehyde:
  • Nitro ⁇ e E was prepared according to the following reaction scheme starting from 3- hydroxybenzaldehyde:
  • Nitrone G has a meiting point of 117°C and is miscible with other resins
  • the starting dimesylate was prepared according to the following reaction scheme:
  • the diaidehyde was prepared from the dimesyiate according to the following reaction scheme:
  • R long chain alkyl group
  • R long chain alkyl group
  • the above nitrones were formulated into curable compositions comprising one or more of the following resins in various molar ratios.
  • the compositions contained no solvent
  • the neat resins and compositions were cured by Differential Scanning Calorimetry (DSC) and the cure temperatures (Cure T1 and Cure T2) and heats of polymerization ( ⁇ H) recorded in the table for each example. (Melting points noted above were also determined by DSC.) Th ermo-grava metric Analysis (TGA) was used to determine weight loss and was performed on TGA (TA 2950) instrument.
  • DSC Differential Scanning Calorimetry
  • ⁇ H heats of polymerization
  • TMI TrisMaleimide
  • C 36 represents a linear or branched chain (with or without cyclic moieties) of 36 carbon atoms
  • EXAMPLE 9 DSC FOR COMPOSITIONS CONTAINING NITRONE A AND CYANATE ESTER Nitrone A was blended with cyanate ester (CE) in various molar ratios. The DSC scans indicated a two stage curing process and an increase in curing temperature as the amount of nitrone decreased. The results are reported in Table 1
  • EXAMPLE 10 DSC FOR COMPOSITIONS CONTAINING NITRONE A 1 CYANATE ESTER
  • Nitrone A in combination with epoxy was tested by TGA for weight loss at 200 0 C and compared to control samples of cyanate ester, epoxy, and a composition of a 1 : 1 molar ratio of cyanate ester and epoxy The results are reported in Table 3
  • EXAMPLE 12 DSC FOR COMPOSITIONS CONTAINING NITRONE C, CYANATE ESTER, EPOXY, MALEIMIDE, AND ACRYLATE
  • Nitrone C was blended with cyanate ester, cyanate ester and epoxy, maleimide, and acrylate, and cured by DSC The results are reported in Table 4 and indicate that the introduction of an aliphatic backbone into the nitrone will decrease the heat of polymerization, for example, compared to Nitrone A [0051] TABLE 4: DSC DATA FOR NITRONE C, CYANATE ESTER, EPOXY, MALEIMIDE, AND
  • EXAMPLE 13 DSC FOR COMPOSITIONS CONTAINING NITRONE D, CYANATE ESTER, EPOXY, ACRYLATE, AND MALEIMIDE
  • Nitrone D has one nitrone functionality and one phenolic functionality Nitrone D was blended with cyanate ester, cyanate ester and epoxy, maleimide, and acrylate, and cured by DSC The results are reported in Table 5 and indicate a two stage curing process Those formulations that did not show a second cure peak reacted completely in the first exotherm
  • Nitrones D and E presents an opportunity to add additional functionality and/or molecular weight and/or aromaticity to these nitrones
  • the phenolic group can be reacted with a compound or resin having a functionality reactive with the phenolic hydroxyl group That compound may contain an additional functionality not reactive with the phenolic hydroxyl, therebv adding that additional functionality to the nitrone
  • the compound may be composed of aliphatic chains of various lengths and branching, or aliphatic groups in combination with aromatic groups to add molecular weight and/or aromaticity to the nitrone
  • Such nitro ⁇ es are included in this invention
  • EXAMPLE 14 DSC FOR COMPOSITIONS CONTAINING NITRONE E 1 CYANATE ESTER, EPOXY, ACRYLATE AND MALEIMIDE
  • Nitrone E was blended with cyanate ester, cyanate ester and epoxy, maleimide, and acrylate, and cured by DSC The results are reported in Table 6 and indicate that Nitrone E cures some compounds slower than Nitrone D
  • EXAMPLE 15 DSC FOR COMPOSITIONS CONTAINING NITRONE AND EPOXY
  • Nitrones are also capable of ring opening, and thus, for example, epoxy or oxetane rings will open initiated by the nitrone dipoie Several nitrones were used in combination with epoxy and cured by DSC The results are reported in Table 9
  • EXAMPLE 16 PROPERTIES FOR COMPOSITIONS CONTAINING NITRONE F, ACRYLATE, EPOXY, MALEIMIDE, AND CYANATE ESTER
  • Nitrone F exhibited a melting point of 132°C with a heat of polymerization of 1531 J/g in neat form, as measured by DSC. It was compatible with other resins. TLC analysis indicated Nitrone F to be appreciably non-polar DSC data is reported in Table 10.
  • EXAMPLE 17 DSC AND TGA OF NITRONE G AND MALEIMIDE, ACRYLATE, AND CYANATE ESTER
  • Nitrone G exhibited considerably less heat of polymerization than any of the Nitrones A to F indicating that the ⁇ H can be reduced by increasing the molecular weight of the nitrone All of the Nitrone G compositions exhibited good thermal stability showing less than 10% weight loss at 200 0 C.
  • EXAMPLE 18 TGA AND DSC FOR COMPOSITIONS CONTAINING NITRONE H ACRYLATE, CYANATE ESTER, AND BISMALEIMIDE
  • Nitrone H was evaluated by DSC (differential scanning calo ⁇ metry) and TGA (thermal gravimetric analysis) performance in various resin formulations TGA results indicated that Nitrone H exhibited good thermal stability and the blend with cyanate ester exhibited minimum weight loss at 0 37% at 200 0 C The results are disclosed in the Table 15
  • Table 15 TGA AND DSC DATA FOR NITRONE H, ACRYLATE CYANATE ESTER, AND BISMALEIMIDE
  • compositions are useful as adhesives and encapsulants particularly within the semiconductor packaging industry They can be used as attach adhesives for adhering a semiconductor die (which includes a semiconductor die package) to a substrate as shown in Figure 1 , and as encapsulants for underfilling the gap caused by solder joints connecting semiconductors to substrates or as an encapsulant for covering and protecting a semiconductor package as shown in Figure 2
  • this invention is a semiconductor adhered to a substrate with a composition as herein described, and a semiconductor electrically connected to a substrate by solder joints in which a gap formed between the semiconductor and substrate by the solder joints is filled with a composition as herein described

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  • Chemical & Material Sciences (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une composition durcissable comprenant une nitrone multifonctionnelle et un autre composé, tel que acrylate, maléimide, ester de cyanate, ou époxy. La nitrone subit une réticulation avec l'autre composé par le biais d'une cycloaddition ou par ouverture de noyau par médiation dipole de nitrone, sans sensibilité à l'oxygéne subi par le durcissage radicalaire libre. Formule (I) et formule (II).
PCT/US2008/062904 2008-05-07 2008-05-07 Nitrones multifonctionnelles dans des systèmes non radicalaires WO2009136920A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US2008/062904 WO2009136920A1 (fr) 2008-05-07 2008-05-07 Nitrones multifonctionnelles dans des systèmes non radicalaires
TW097120662A TW200946560A (en) 2008-05-07 2008-06-04 Multifunctional nitrones in non-radical systems

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PCT/US2008/062904 WO2009136920A1 (fr) 2008-05-07 2008-05-07 Nitrones multifonctionnelles dans des systèmes non radicalaires

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011088787A1 (de) 2011-12-16 2013-06-20 Evonik Industries Ag Siloxannitrone und deren Anwendung
WO2015052131A1 (fr) 2013-10-08 2015-04-16 Compagnie Generale Des Etablissements Michelin Composition de caoutchouc pour bande de roulement comprenant une polynitrone
WO2023148380A1 (fr) * 2022-02-07 2023-08-10 Cinartis Gmbh Composition de peinture en poudre
FR3136776A1 (fr) 2022-06-20 2023-12-22 Compagnie Generale Des Etablissements Michelin Composition de caoutchouc diénique comprenant une polynitrone.

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988229A (en) * 1975-08-28 1976-10-26 Eastman Kodak Company Stabilized photopolymerizable polymeric compositions containing a photoinitiator and a nitrone derivative
JPH08209027A (ja) * 1994-09-12 1996-08-13 General Electric Co <Ge> 放射線硬化可能なケイ素含有ポリアクリレートハードコート組成物の製造方法とそれによって製造された組成物
KR20060134831A (ko) * 2005-06-23 2006-12-28 내쇼날 스타치 앤드 케미칼 인베스트멘트 홀딩 코포레이션 도전성 향상제용 유기산 금속염
KR20070026468A (ko) * 2004-04-23 2007-03-08 엥거스 케미칼 캄파니 신규한 페놀 수지
US20070055041A1 (en) * 2002-12-04 2007-03-08 Swedo Raymond J Novel phenolic resins
JP2007269969A (ja) * 2006-03-31 2007-10-18 Nof Corp 光硬化性樹脂組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988229A (en) * 1975-08-28 1976-10-26 Eastman Kodak Company Stabilized photopolymerizable polymeric compositions containing a photoinitiator and a nitrone derivative
JPH08209027A (ja) * 1994-09-12 1996-08-13 General Electric Co <Ge> 放射線硬化可能なケイ素含有ポリアクリレートハードコート組成物の製造方法とそれによって製造された組成物
US20070055041A1 (en) * 2002-12-04 2007-03-08 Swedo Raymond J Novel phenolic resins
KR20070026468A (ko) * 2004-04-23 2007-03-08 엥거스 케미칼 캄파니 신규한 페놀 수지
KR20060134831A (ko) * 2005-06-23 2006-12-28 내쇼날 스타치 앤드 케미칼 인베스트멘트 홀딩 코포레이션 도전성 향상제용 유기산 금속염
JP2007269969A (ja) * 2006-03-31 2007-10-18 Nof Corp 光硬化性樹脂組成物

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011088787A1 (de) 2011-12-16 2013-06-20 Evonik Industries Ag Siloxannitrone und deren Anwendung
EP2607437A1 (fr) 2011-12-16 2013-06-26 Evonik Industries AG Siloxane-nitrone et son utilisation
US8722836B2 (en) 2011-12-16 2014-05-13 Evonik Industries Ag Siloxane nitrones and use thereof
WO2015052131A1 (fr) 2013-10-08 2015-04-16 Compagnie Generale Des Etablissements Michelin Composition de caoutchouc pour bande de roulement comprenant une polynitrone
WO2023148380A1 (fr) * 2022-02-07 2023-08-10 Cinartis Gmbh Composition de peinture en poudre
FR3136776A1 (fr) 2022-06-20 2023-12-22 Compagnie Generale Des Etablissements Michelin Composition de caoutchouc diénique comprenant une polynitrone.
WO2023247199A1 (fr) 2022-06-20 2023-12-28 Compagnie Generale Des Etablissements Michelin Composition de caoutchouc diénique comprenant une polynitrone

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