WO2000076764A1 - Resine epoxyde, copolymere styrene-anhydride maleique et plastifiant - Google Patents

Resine epoxyde, copolymere styrene-anhydride maleique et plastifiant Download PDF

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Publication number
WO2000076764A1
WO2000076764A1 PCT/US2000/013147 US0013147W WO0076764A1 WO 2000076764 A1 WO2000076764 A1 WO 2000076764A1 US 0013147 W US0013147 W US 0013147W WO 0076764 A1 WO0076764 A1 WO 0076764A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
matter
resin composition
flexibilizer
styrene
Prior art date
Application number
PCT/US2000/013147
Other languages
English (en)
Inventor
Eric L. Holman
Nancy M.W. Androff
Michael A. Petti
Original Assignee
Isola Laminate Systems Corp.
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 Isola Laminate Systems Corp. filed Critical Isola Laminate Systems Corp.
Publication of WO2000076764A1 publication Critical patent/WO2000076764A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
    • B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/04—Layered products comprising a layer of synthetic resin as impregnant, bonding, or embedding substance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/02—Composition of the impregnated, bonded or embedded layer
    • B32B2260/021—Fibrous or filamentary layer
    • B32B2260/023—Two or more layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
    • B32B2260/04—Impregnation, embedding, or binder material
    • B32B2260/046—Synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2363/00—Epoxy resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/08—PCBs, i.e. printed circuit boards
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0326—Organic insulating material consisting of one material containing O

Definitions

  • This invention concerns epoxy resin compositions comprising a styrene malic
  • resin compositions including a cyclic ketone solvent which improves resin
  • This invention also concerns high T g laminates prepared using resin compositions
  • Cured and partially cured epoxy resins are used in prepregs and laminates.
  • the bath contains one or more organic radicals, e.g., one or more organic radicals, and one or more organic radicals.
  • the reinforcing material is resident in the bath for a time sufficient to coat it with the resin system.
  • the heating zone is held at a temperature of between 120°C and 200 °C.
  • the residence time in the zone is sufficient to allow the
  • Such a b-stage product is also referred to as a prepreg.
  • the prepregs may be stacked and formed into a shape, such as a circuit board or a circuit board component, and exposed to
  • the circuit board be manufactured from resins that were to a low dielectric constant and a high glass transition temperature (T g ).
  • T g glass transition temperature
  • Brittleness refers to the tendency of the circuit board to craze on the edges and around
  • prepregs and circuit board products manufactured therefrom that do not exhibit undesirable brittleness but that maintain their desirable high glass transition temperatures and low
  • Yet another aspect of this invention is a resin system including a phenoxy compound that exhibits good pre-cure shelf-life and stability.
  • this invention includes a resin composition of matter comprising at least one epoxy resin, a copolymer of styrene and maleic anhydride, and at least one flexibilizer.
  • this invention includes a resin composition of matter comprising at least one epoxy resin, a copolymer of styrene and maleic anhydride, at least one catalyst; and from about 0.2 to about 20 wt% of at least one phenoxy resin includes a reactive group that reacts with anhydride.
  • this invention includes a resin composition of matter comprising at least one epoxy resin, a copolymer of styrene and maleic anhydride, at least one phenoxy resin that includes a reactive group; and solvent system further comprising cyclohexanone.
  • this invention includes a resin composition of matter comprising at least one epoxy resin, a copolymer of styrene and maleic anhydride, at least one phenoxy resin that has a reactive group, cyclohexanone; and methylethylketone.
  • This invention also includes prepregs, composites, and circuit boards manufactured with one or more resins of this invention. DESCRIPTION OF THE CURRENT EMBODIMENT
  • the present invention relates to thermosetting resin compositions comprising at least one epoxy resin, a curing agent, and at least one hydroxy functional flexibilizer.
  • the present invention also relates to resin compositions including a phenoxy resin flexibilizer along with a solvent that improves the stability of the phenoxy resin containing composition.
  • the resin compositions of this invention include at least one epoxy resin, a copolymer of styrene and maleic anhydride, and at least one hydroxy functional flexibilizer.
  • the resin is typically dissolved or dispersed to form a varnish using one or more solvents.
  • a preferred resin composition of this invention will include a solvent that is able to dissolve or disperse the resin ingredients to produce a resin varnish with good stability.
  • the wt% values of the resin ingredients given herein are on a solution (varnish) basis. That is, the ingredient wt% is based upon a varnish that includes a resin system dissolved and/or dispersed in solvent.
  • the compositions of this invention include one or more epoxy resins.
  • the epoxy resins selected may include one or more epoxy moiety per resin molecule.
  • the epoxy is a polyepoxide which includes partially advanced epoxy resins, i.e., the reaction of a polyepoxide and a curing agent, wherein the reaction product has an average of at least one unreacted epoxide unit per molecule. Examples of polyepoxides useful in this invention are disclosed in U.S. Patent No. 5,314,720, the specification of which is incorporated herein by reference.
  • the resin compositions of this invention will include from about 27 to about 47 wt% epoxide resin. Preferably, the resin compositions will include from about 32 to about 42 wt%.
  • the resin composition of this invention also include a curing agent that is a copolymer of styrene and maleic anhydride (SMA).
  • SMA curing agent should be present in compositions of this invention in an amount ranging from about 16 to about 36 wt% and preferably in amount ranging from about 21 to about 31 wt%.
  • the combination of an epoxy resin and a curing agent that is a copolymer of styrene and maleic anhydride produces a cured resin product having a high T g and a low dielectric constant.
  • the resin product is very brittle in comparison to resin products manufactured using other resins and curing agents.
  • the compositions of this invention include at least one flexibilizer.
  • the term "flexibilizer” refers to any linear polymer having a molecular weight greater than 5000 that includes at least one anhydride reactive functionality.
  • Preferred flexibilizers are phenoxy resins (polyhydroxyethers). The flexibilizer chosen exhibit some reactivity towards the anydride containing curing agent.
  • the flexibilizer may be any hydroxy, and/or amine functional flexibilizer, and in particular one ore more phenoxy resin that has hydroxy or amine groups that reacts with anhydrides.
  • hydroxy functionalities include alcohols, acids, carboxylic acids and mixtures thereof.
  • the chosen hydroxy and/or amine functional flexibilizer should include one or more reactive functionalities.
  • the flexibilizer and in particular the preferred phenoxy resin flexibilizer should have a molecular weight ranging from about 5000 to 16,000.
  • the flexibilizer will have a molecular weight ranging from about 10,000 to about 16,000.
  • the molecular weights referred to herein are number average molecular weights.
  • the flexibilizer and in particular the phenoxy resin flexibilizers should be present in the resin compositions in an amount sufficient to improve the cured resin brittleness while having little impact on the cured resin Tg. It is preferred that the addition of the compositions include an amount of flexibilizing agents that will depress the resulting cured resins Tg no more than 5% in comparison to resins without the flexibilizing agent. Generally, the resin
  • systems of this invention may include from about 0.2 to about 20 wt phenoxy with from about 3 to about 15 wt% being preferred and from about 6 to about 12 wt% being most preferred.
  • the resin compositions of this invention will typically include a catalyst.
  • Any catalyst capable of facilitating the reaction of the epoxide with the SMA curing agent may be incorporated into the resin compositions of this invention.
  • useful catalysts include zinc carboxylate, organo zinc chelate compounds, quaternary phosphonium and ammonium salts, tertiary amines, imidazole compounds, boric acid, and mixtures thereof.
  • Preferred catalyst include boric acid, 2-ethyl-4-methylimidazole, 2-methylimidazole, 2- phenylimidizole, and mixtures thereof.
  • the catalyst is generally incorporated in the resin system in amount ranging from about 0.01 to 2 wt% and preferably in an amount ranging from about 0.02 to about 1 wt%.
  • the resin systems of this invention are typically combined with solvents to form what is referred to as a varnish for ease of application of the resin system to a base material.
  • a varnish for ease of application of the resin system to a base material.
  • the resin compositions of this invention including hydroxy functional flexibilizer were dissolved and solublized in a solvent, it was discovered that the resin system became less stable in comparison to resin systems without a hydroxy functional flexibilizer.
  • another aspect of this invention is a resin system including a hydroxy functional flexibilizer that is dissolved in a solvent that improves the resin system stability.
  • a cyclic ketone solvent, and in particular cyclohexanone significantly improves resin stability.
  • the cyclic ketone solvent and in particular, cyclohexanone may be used alone or in conjunction with one ' or more compatible solvents.
  • suitable solvents include ketones such as MEK, acetone, MAK, MiBK, aromatic solvents such as tolene and xylene, glycol ethers such as PMA, and compatible mixtures thereof.
  • the solvent used to produce the varnish of this invention include a mixture of cyclohexanone and methylethyl ketone in a weight ratio of from about 9:1 to about 1:9. It is most preferred that the solvent used to prepare varnishes of this invention include about a 7:3 weight ratio of cyclohexanone to methylketone.
  • the resin compositions and varnishes of this invention are useful when applied to a base material such as a copper foil surface to make a resin coated copper for and/or a reinforcing material such as paper, glass fiber, inorganic fiber and so forth.
  • the resin compositions and varnish can be applied to the base material in any suitable manner such as by spraying, dipping, soaking, injecting or otherwise coating the resin composition thereon.
  • a preferred reinforcing material that is useful in conjunction with the cyclic ketone containing varnishes of this invention is aramid fiber reinforcing materials such as Thermount manufactured by DuPont de Nemours. It is well known that aramid fiber reinforcing materials are incompatible DMF (dimethylformamide) and similar varnish solvents. Thus, the use of a varnish containing at least one cyclic ketone as a aramid fiber impregnation solution overcomes the compatability issues associated with prior art varnishes.
  • the aramid fiber is preferably impregnated with varnish of this invention and b-staged to produce a prepreg that is useful in the subsequent manufacture of electronic substrates.
  • the resin/base material combination may be partially cured to produce a b-stage material, also known as a prepreg, or it may be completely cured to give a c-stage material.
  • the b-stage and c-stage materials may be associated with one another or with other electric substrate materials such as metal foils, dielectric layers and so forth by any means known in the art to form composites that are useful in electronic substrates such as multilayer circuit boards and the like.
  • Laminates prepared with and without a phenoxy resin in the resin system were prepared and the properties and drillability of the laminates were evaluated.
  • the laminates were prepared in a standard heat lamination process.
  • the varnish was
  • the woven mat was b-staged to
  • each prepreg had a thickness of about 0.004" .
  • laminate plies each including about 45 wt% retained resin were stacked one on top of the other to give a thickness of 0.08" and sandwiched between two layers of 1 oz HTE copper foil manufactured by Gould Electronics.
  • the copper/laminate sandwich was cured in a
  • the partially cured prepregs have properties essentially identical to prepregs

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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)
  • Reinforced Plastic Materials (AREA)

Abstract

L'invention concerne une composition utile en tant que préimprégné pour une carte à circuits imprimés, cette composition résultant de la recherche d'un équilibre entre flexibilité, température élevée de transition vitreuse et faible constante diélectrique. Cette composition comprend une résine époxyde, un copolymère styrène-anhydride maléique, un plastifiant tel qu'une résine phénoxy contenant éventuellement des groupes hydroxy, et éventuellement un système de solvants tel qu'un mélange de cyclohexanone et de méthyléthylcétone.
PCT/US2000/013147 1999-06-10 2000-05-10 Resine epoxyde, copolymere styrene-anhydride maleique et plastifiant WO2000076764A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US32996999A 1999-06-10 1999-06-10
US09/329,969 1999-06-10

Publications (1)

Publication Number Publication Date
WO2000076764A1 true WO2000076764A1 (fr) 2000-12-21

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1418206A1 (fr) * 2002-10-19 2004-05-12 LEUNA-Harze GmbH Composition de resine Epoxy reticulable
WO2004048470A1 (fr) * 2002-11-26 2004-06-10 Dow Global Technologies Inc. Composition de durcissement pour resines epoxydes
WO2008051373A2 (fr) * 2006-10-19 2008-05-02 Dow Global Technologies Inc. Compositions de résine époxy durcissables ayant une meilleure adhérence sur les substrats métalliques et leurs procédés de fabrication et d'utilisation
WO2011056352A1 (fr) * 2009-11-06 2011-05-12 Dow Global Technologies Llc Compositions de résine époxy stables à la conservation pour stratifiés électriques
CN107298831A (zh) * 2017-07-20 2017-10-27 南亚新材料科技股份有限公司 改善耐漏电起痕指数及钻孔加工性能半固化片及其应用
CN107708333A (zh) * 2017-10-17 2018-02-16 珠海市宏广科技有限公司 新能源汽车电池减铜电路板制备方法

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49109476A (fr) * 1973-02-21 1974-10-17
US3936575A (en) * 1973-02-21 1976-02-03 Sumitomo Bakelite Company, Limited Flexible metal-clad laminates and method for manufacturing the same
US4212959A (en) * 1978-05-09 1980-07-15 Mitsubishi Denki Kabushiki Kaisha Heat resistant resin composition
US4212960A (en) * 1977-11-05 1980-07-15 Mitsubishi Denki Kabushiki Kaisha Epoxy resin composition
JPS5894461A (ja) * 1981-12-01 1983-06-04 松下電工株式会社 白色エポキシ樹脂積層板
US4591623A (en) * 1984-06-15 1986-05-27 Mitsubishi Denki Kabushiki Kaisha Thermosetting resin composition
DE3839105A1 (de) * 1987-11-19 1989-06-01 Dainippon Ink & Chemicals Epoxyharzmasse
JPH01221413A (ja) * 1987-11-19 1989-09-04 Dainippon Ink & Chem Inc エポキシ樹脂組成物及びこれを用いたプレプリグと積層板の製法
JPH0925349A (ja) * 1995-07-11 1997-01-28 Mitsubishi Gas Chem Co Inc プリプレグ及び積層板
JPH09143445A (ja) * 1995-11-21 1997-06-03 Hitachi Chem Co Ltd 回路用接続部材

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49109476A (fr) * 1973-02-21 1974-10-17
US3936575A (en) * 1973-02-21 1976-02-03 Sumitomo Bakelite Company, Limited Flexible metal-clad laminates and method for manufacturing the same
US4212960A (en) * 1977-11-05 1980-07-15 Mitsubishi Denki Kabushiki Kaisha Epoxy resin composition
US4212959A (en) * 1978-05-09 1980-07-15 Mitsubishi Denki Kabushiki Kaisha Heat resistant resin composition
JPS5894461A (ja) * 1981-12-01 1983-06-04 松下電工株式会社 白色エポキシ樹脂積層板
US4591623A (en) * 1984-06-15 1986-05-27 Mitsubishi Denki Kabushiki Kaisha Thermosetting resin composition
DE3839105A1 (de) * 1987-11-19 1989-06-01 Dainippon Ink & Chemicals Epoxyharzmasse
JPH01221413A (ja) * 1987-11-19 1989-09-04 Dainippon Ink & Chem Inc エポキシ樹脂組成物及びこれを用いたプレプリグと積層板の製法
JPH0925349A (ja) * 1995-07-11 1997-01-28 Mitsubishi Gas Chem Co Inc プリプレグ及び積層板
JPH09143445A (ja) * 1995-11-21 1997-06-03 Hitachi Chem Co Ltd 回路用接続部材

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1418206A1 (fr) * 2002-10-19 2004-05-12 LEUNA-Harze GmbH Composition de resine Epoxy reticulable
WO2004048470A1 (fr) * 2002-11-26 2004-06-10 Dow Global Technologies Inc. Composition de durcissement pour resines epoxydes
US7547745B2 (en) 2002-11-26 2009-06-16 Dow Global Technologies, Inc. Epoxy resin hardener of anhydride copolymer and anhydride-elastomer copolymer
WO2008051373A2 (fr) * 2006-10-19 2008-05-02 Dow Global Technologies Inc. Compositions de résine époxy durcissables ayant une meilleure adhérence sur les substrats métalliques et leurs procédés de fabrication et d'utilisation
WO2008051373A3 (fr) * 2006-10-19 2008-06-19 Dow Global Technologies Inc Compositions de résine époxy durcissables ayant une meilleure adhérence sur les substrats métalliques et leurs procédés de fabrication et d'utilisation
US8877866B2 (en) 2006-10-19 2014-11-04 Dow Global Technologies Llc Curable epoxy resin compositions having improved adhesion to metal substrates and processes for making and using the same
WO2011056352A1 (fr) * 2009-11-06 2011-05-12 Dow Global Technologies Llc Compositions de résine époxy stables à la conservation pour stratifiés électriques
US8980376B2 (en) 2009-11-06 2015-03-17 Dow Global Technologies Llc Storage stable epoxy resin compositions for electrical laminates
CN107298831A (zh) * 2017-07-20 2017-10-27 南亚新材料科技股份有限公司 改善耐漏电起痕指数及钻孔加工性能半固化片及其应用
CN107708333A (zh) * 2017-10-17 2018-02-16 珠海市宏广科技有限公司 新能源汽车电池减铜电路板制备方法
CN107708333B (zh) * 2017-10-17 2021-08-03 珠海市宏广科技有限公司 新能源汽车电池减铜电路板制备方法

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