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WO1986004079A1 - Compositions de poly(imides) possedant des diamines de phenylindane et/ou des moities de dianhydride dans la colonne vertebrale du poly(imide) - Google Patents

Compositions de poly(imides) possedant des diamines de phenylindane et/ou des moities de dianhydride dans la colonne vertebrale du poly(imide) Download PDF

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Publication number
WO1986004079A1
WO1986004079A1 PCT/US1985/002588 US8502588W WO8604079A1 WO 1986004079 A1 WO1986004079 A1 WO 1986004079A1 US 8502588 W US8502588 W US 8502588W WO 8604079 A1 WO8604079 A1 WO 8604079A1
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Prior art keywords
poly
composition according
composition
imide
polymeric component
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Ceased
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PCT/US1985/002588
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English (en)
Inventor
Rafael Camargo
Frank Mercer
Tai Chun Cheng
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Raychem Corp
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Raychem Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds

Definitions

  • This invention relates to novel polymeric compositions and the composition after it has been cured.
  • the invention relates to polymeric compositions comprising a poly(imide) selected from poly(imides) having phenylindane diamine and/or dianhydride moieties in the poly(imide) backbone and a polymeric component.
  • poly(imides) having phenylidane diamine and/or dianhydride moieties in the poly(imide) backbone are described in U.S. Patent No. 3,856,752, incorporated herein by reference.
  • a preferred such poly(imide) of the composition is XU218 from Ciba-Geigy which is of the formula:
  • n is greater than 1.
  • These polymers are known to be useful as shaped structures, self-supporting films, fibers, filaments and coatings. They, generally, have high tensile strength, are susceptible to hydrolysis, are infusible, insoluble, and stable to heat. They may be used in corrosion resistant pipes, pipe-lagging and duct work, a lining therefore for containers and in laminating structures where the polymers are bonded to the sheet metal or foils, oven interiors, electrical insulation and semiconductor coatings.
  • Poly(imides) are known to produce resins with high strength, rigidity, thermal stability, high continuous use temperature and solvent resistance.
  • One of the problems that has been encountered in the use of poly(imides) is the tendency of the polymers to crack. Further, when used as adhesives and coatings the adhesion between the polymer and various substrates can be less than required for high performance applications.
  • compositions of poly(imides) selected from poly(imides) having phenylindane diamines and/or dianhydride moieties incorporated into the poly(imide) backbone and a polymeric component comprising:
  • compositions which have been cured are useful for their improved adhesive properties, solvent cracking resistance, high temperature properties and are useful as coatings especially for semiconductors and are melt processable or melt fusible. Even further, it has been discovered that the compositions are useful as the matrix resin for reinforced composites.
  • the composition is also useful in making an article comprising a substrate having on a surface thereof at least one layer of the cured composition of the invention.
  • the poly(imide) component comprises from about 99% to about 1% by weight of the composition and the polymeric component comprises from about 1% to about 99% to the composition. It is further preferred that the polymer component comprise at least about 25%, by weight of the composition. It is further preferred that the poly(imide) component comprise from about 15% to about 75% by weight of the composition.
  • compositions of this invention comprise the polymeric component as described above.
  • the polymeric component may contain additional components as set forth in detail below.
  • poly(etherimides) suitable for use in this invention are well known in the art and described in, for example, U.S. Patent Nos. 3,847,867, 3,838,097 and 4,107,147, incorporated herein by reference.
  • a preferred poly(etherimide) has the structure
  • n is greater than 1 but preferably from about 10 to about 10,000 or more and is available, for example, as Ultem D-1000 (General Electric) a high molecular weight, amorphous and melt processable polymer.
  • Poly (sulfones) suitable for use in this invention are well known and comprise linear thermoplastic polyarylene polyethers wherein the arylene units are interspersed with a sulfone linkage. These polymers may be obtained by reaction of an alkali metal double salt of a dihydric phenol and a dihalobenzenoid or dinitrobenzenoid compound either or both which contain a sulfone linkage, i.e. -SO 2 -, between arylene groupings, to provide sulfone units in the polymerchain. Polymers of this sort are further described in US Patent 4,293,670 incorporated herein by reference. Preferred poly (sulfones) are of the formula:
  • n is greater than 1 but preferably from about 10 to about 10,000 or more and the poly(ether sulfone) having the formula:
  • n is greater than 1 but preferably from about 10 to about 10,000 or more.
  • Poly (aryl ether ketones) suitable for use in this invention have the repeat units of the formula:
  • Ar and Ar' are aromatic moieties at least one of which contains a diaryl ether linkage forming part of the polymer backbone and wherein both Ar and Ar' are covalently linked to the carbonyl groups through aromatic carbon atoms.
  • Ar and Ar' are independently selected from substituted and unsubstituted phenylene and substituted and unsubstituted polynuclear aromatic moieties.
  • polynuclear aromatic moieites is used to mean aromatic moieties containing at least two aromatic rings. The rings can be fused, joined by a direct bond or by a linking group.
  • linking groups include for example, carbonyl, ether sulfone, sulfide, amide, imide, azo, alkylene, perfluoro-alkylene and the like.
  • Ar and Ar' contains a diaryl ether linkage.
  • the phenylene and polynuclear aromatic moieties can contain substituents on the aromatic rings. These substi-tuents should not inhibit or otherwise interfere with the polymerization reaction to any significant extent.
  • substituents include, for example, phenyl, halogen, nitro, cyano, alkyl, 2-alkynyl and the like.
  • Poly(aryl ether ketones) having the following repeat units are preferred:
  • Poly(aryl ether ketones) can be prepared by known methods of synthesis.
  • Preferred poly(aryl ether ketones) can be prepared by Friedel-Crafts polymerization of a monomer system comprising:
  • each Ar" is independently selected from substituted or unsubstituted phenylene, and substituted and unsubstituted polynuclear aromatic moieties free of ketone carbonyl or ether oxygen groups, in the presence of a reaction medium comprising:
  • a Lewis acid in an amount of one equivalent per equivalent of carbonyl groups present, plus one equivalent per equivalent of Lewis base, plus an amount effective to act as a catalyst for the polymerization;
  • the aromatic diacid dihalide employed is preferably a dichloride or dibromide.
  • Illustrative diacid dihalides which can be used include, for example
  • Illustrated polynuclear aromatic comonomers which can be used with such diacid halides are:
  • H-Ar"-O-Ar"-H which includes, for example:
  • Monomer systems II and III comprise an acid halide.
  • acid halide is used herein to refer to a monoacid monohalide .
  • the acid halide is of the formula:
  • monomers can be employed.
  • one or more diacid dihalides can be used with one or more, polynuclear aromatic comonomers as long as the correct stoichiometry is maintained.
  • one or more acid halides can be included.
  • monomers which contain other linkages such as those specified above, can be employed as long a one or more of the comonomers used contains at least one ether oxygen linkage.
  • Such comonomers include for example:
  • the monomer system can also contain up to about 30 mole % of a comonomer such as a sulfonyl chloride which polymerizes under Friedel-Crafts conditions to provide ketone/sulfone copolymers.
  • a comonomer such as a sulfonyl chloride which polymerizes under Friedel-Crafts conditions to provide ketone/sulfone copolymers.
  • polystyrene resin suitable for use in the invention are well known and are thermoplastic linear polyesters of carbonic acid, made by the polymeric condensation of bisphenols with a phosgene or its derivatives. These polymers are known for their excellent properties of toughness, flexibility, impact strength, optical clarity and heat resistance. More recent representative examples are included in U.S. Patent Nos. 4,469,861, 4,469,833, 4,469,860, 4,469,852, 4,469,850 and 4,469,838.
  • Preferred poly(carbonates) include any of the Lexan grades available from General Electric which have the general formula:
  • n is greater than 1 but preferably from about 10 to about 10,000 or more.
  • Poly (arylates) suitable for use in the invention are aromatic polyesters derived from a dihydric phenol, particularly bisphenol A and an aromatic dicarboxylic acid, particularly mixtures of terephthalic and isophthalic acids. See for example and further definition U.S. Patent Nos. 4,246,381 and 4,250,279 incorporated herein by reference.
  • a preferred poly(arylate) is of the formula:
  • n is greater than 1 but preferably from about 10 to about 10,000 or more, commercially available from Union Carbide under the trade name of Ardel in a number of grades which differ in average molecular weight.
  • poly(imides) having phenylindane diamine and/or dianhydride moieties in the poly (imide) backbone and one or more poly (etherimide), poly (sulfone), poly(aryl ether ketone); poly (arylate) or poly (carbonate) can be present in the composition to provide the desired physical properties of the final article.
  • the polymers or copolymers can be used in any of the various commercial grades which may vary in average molecular weights, molecular weight distributions and may contain minor amounts of comonomer residues and the like.
  • blends of two or more polymers contain the separate polymers as individual components domains or phases.
  • blends of what are termed compatible polymers generally are mechani cally compatible only and exhibit properties which vary widely over the concentration range of the polymers.
  • Such blends comprise a matrix polymer containing the other polymer as a dispersed or co-continuous phase.
  • Such dispersed phases can be microscopic in size sometimes giving the resulting blend of multiple phases the appearance of being a single phase.
  • polymers which are molecularly compatible that is, they form a molecularly dispersed mixture comprising a single amorphous phase when they are blended together.
  • glass transition temperature is meant the temperature at which an amorphous polymer or the amorphous regions of a partially crystalline polymer changes to or from a hard and relatively brittle state to a more flexible or rubbery condition. Measurement of glass transition temperatures of polymer systems is described, for example, in Thermal Characterization Techniques, Slade, et al., Marcel Dekker, Inc., New York (1970).
  • blends of the invention consisting of a poly(imide) and a poly (ether imide) and which may further contain a poly (aryl ether ketone), as described above, are molecularly compatible.
  • Blends of the molecularly compatible polymers are characterized in that they comprise a single amorphous phase although one or more of the individual polymers may also have crystalline portions which may exist as a separate phase.
  • One aspect of this degree of compatibility is that the amorphous phase exhibits a single glass transition temperature as defined above.
  • compositions of the invention can contain various additives in addition in order to give any desired property to the composition.
  • additives for example, stabilizers, flame retardants, pigments, plasticizers, surfactants, antioxidants and the like can be present.
  • Compatible or non-compatible polymers may also be added to give desired properties.
  • the composition can be prepared by any convenient technique.
  • the components can be mixed on a two-roll mill, in an internal mixer such as a Brabender mixer or Banbury mixer, or in a twin-screw extruder. They may also be prepared by precipitation from a solvent, or cast from solution or the like.
  • the compositions can be substantially cured preferably at elevated temperature i.e. 250-350°C for 30 min. to 3 hours. Where appropriate, the composition may also be cured by radiator or other means appropriate to the components selected.
  • a shaped article of the composition can be formed before or after cure by known techniques depending on the desired shape.
  • Films or coatings of the blend can be formed by extrusion, spraying, spin coating or casting, fibers by melt spinning or the like.
  • Other articles may be injection molded, compression molded, pour molded, blow molded or the like with or without additives as previously described.
  • compositions of the invention are useful adhesives and semiconductor coatings which include alpha particle barriers, coatings for passivation and mechanical protection, and interlayer dielectrics.
  • the invention also relates to a reinforced composition
  • a reinforcing component e.g. carbon, or glass fibers or other polymeric fibers or the like, such as polyamides (e.g. poly (aramide) sold by Dupont under the trade name Kevlar) forming a high strength composite.
  • a reinforcing component e.g. carbon, or glass fibers or other polymeric fibers or the like, such as polyamides (e.g. poly (aramide) sold by Dupont under the trade name Kevlar) forming a high strength composite.
  • polyamides e.g. poly (aramide) sold by Dupont under the trade name Kevlar
  • compositions of this invention are particularly advantageous in the preparation of a layered article, in particular a multi-layered article for use in electronic systems.
  • the article comprises a substrate, for example of glass or ceramic material, with at least one layer comprising a cured, aromatic polymer-based composition of this invention deposited on a surface thereof. Generally a plurality of layers are successively deposited on the substrate and cured.
  • One or more layers of conductive material can be interposed between two adjacent layers of the aromatic polymer based composition.
  • the conductive layer is generally not continuous or coextensive with the adjacent polymeric layers and typically forms a plurality of electrically conductive pathways.
  • the conductive layer is preferably of metal but can comprise a semi-conductive element.
  • the composition used is preferably highly resistant to hydrolysis and has a water absorption of less than about 2%, preferably less than about 1% when contacted with water at 90 °C for 960 minutes.
  • the composition preferably also is a dielectric having a dielectric constant less than about 5, preferably less than about 3.
  • the article is prepared by coating the aromatic polymer in the form of a solution, preferably by a spin coating technique, onto the substrate.
  • the solvent is evaporated and the composition is cured at elevated temperatures.
  • the thickness of the coating is about 5 to 40 microns.
  • the conductive layer is applied over the polymeric layer using, for example, a sputtering technique with appropriate areas masked to create the desired conductive pathways.
  • the next polymeric layer is applied in the same manner as the first. These two steps can be repeated until the desired multi-layered article is produced.
  • the multi-layered article can be used, for example, as a packaging-interconnect device for integrated circuits.
  • the following examples are representative of the invention but not intended to be limiting. Substitution of additives materials, polymers, and conditions which are obvious from this disclosure are within the contemplation of the invention.
  • a Victrex PEEK/ULTEM/XU218 blend was prepared as follows: to 75 ml of methylene chloride was added 6.25g of ULTEM, and 6.25g of XU218. After the solids were totally dissolved, 37.5g of Victrex PEEK powder were added. The slurry was cast on aluminum foil and air dried overnight. The resulting material was further dried for 16 hours at 125°C. The powder was pressed at 400 °C for 3 minutes to yield a transparent plaque (0.7 mm thick).
  • a Victrex PEEK/Ultem (75/25) blend was prepared as described in Example 4, using 12.5g of Ultem and 37.5g of Victrex PEEK. Plaques of Victrex PEEK/Ultem and pure Victrex PEEK were pressed under the same conditions given above (400°C, 3 minutes then quench in cold water press). DSC samples of the three materials were prepared using 17 ⁇ 2 mg. DSC run were done from 50 °C to 380 °C at 40°C/minute. In all four cases, a single Tg was observed, higher for the blends than for pure Victrex PEEK. A summary of DSC data is given below.
  • Samples 1 through 5 were then annealed at 316 °C for 45 minutes. About 0.18 g of sample was placed in vials and 20 ml of concentrated sulfuric acid was added to each vial. After 48 hours samples 4 and 5 had completely dissolved. Samples 1, 2, and 3 on the other hand, were only partially dissolved.
  • a Victrex PEEK/Ultem/XU218 blend (75/20/5) was prepared as described in Example 4, using 750g of Victrex PEEK, 200g of Ultem and 50g of XU218 in 1,000 ml of methylene chloride. The resulting dry powder was extruded without problems on the ZSK twin screw extruder to yield a light amber transparent material of relatively uniform pellet size.
  • Example 7
  • Adhesive bonding conditions are 100 psi, 343 °C for 20 minutes.

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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)
  • Compositions Of Macromolecular Compounds (AREA)
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  • Application Of Or Painting With Fluid Materials (AREA)
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Abstract

Nouvelles compositions à base d'un poly(imide) sélectionné parmi des poly(imides) possédant des diamines de phénylindane et/ou des moitiés de dianhydride dans la colonne vertébrale du poly(imide) et un composant polymère comprenant a) un poly(étherimide); b) un poly(sulfone); c) un poly(aryl éther cétone); d) un poly(carbonate) ou e) un poly(arylate), ainsi que les compositions polymérisées. Ces compositions sont utiles comme adhésifs, revêtements et résines matricielles pour composites renforcés par des fibres. Est également décrit un article multicouche destiné à être utilisé dans des dispositifs électroniques, l'article comprenant une pluralité de couches comprenant chacune une des compositions ci-décrites polymérisées avec une ou plusieurs couches intercalées de matériau conducteur ou semi-conducteur.
PCT/US1985/002588 1985-01-04 1985-12-31 Compositions de poly(imides) possedant des diamines de phenylindane et/ou des moities de dianhydride dans la colonne vertebrale du poly(imide) Ceased WO1986004079A1 (fr)

Applications Claiming Priority (2)

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US68878385A 1985-01-04 1985-01-04
US688,783 1985-01-04

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WO1986004079A1 true WO1986004079A1 (fr) 1986-07-17

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0414124A3 (en) * 1989-08-19 1992-01-22 Hoechst Aktiengesellschaft Multicomponent alloy with a glass transition temperature
US5134202A (en) * 1988-12-30 1992-07-28 Amoco Corporation Process for miscible blends of imide containing polymers with poly(aryl sulfones)
US5286812A (en) * 1988-02-19 1994-02-15 University Of Massachusetts High performance blends of aromatic polyimides with aromatic polyethersulfones
WO1994005404A1 (fr) * 1992-09-02 1994-03-17 L'air Liquide Societe Anonyme Pour L'etude Et L'ex Membranes de separation de gaz fabriquees a partir de melanges depolymeres de polyimide, de polyamide ou de polyamideimide aromatiques
EP0626412A1 (fr) * 1993-04-09 1994-11-30 Ciba-Geigy Ag Oligomères de polyimide
EP0636661A1 (fr) * 1993-07-28 1995-02-01 MITSUI TOATSU CHEMICALS, Inc. Composition de resine de polyimide
EP0778077A3 (fr) * 1995-12-07 1998-01-14 Sakellaropoulos, George Membranes polymères préparées à partir de mélanges de polysulfones et de polyimides pour la séparation de mélanges de gaz industriels
US20170362379A1 (en) * 2014-12-12 2017-12-21 Solvay Specialty Polymers Usa, Llc Poly(aryl ether) compositions for polymer-metal junctions and polymer-metal junctions and corresponding fabrication methods
EP3487904A4 (fr) * 2016-07-25 2020-06-10 The Boeing Company Résine époxy
EP4105273A4 (fr) * 2020-02-13 2024-06-26 Toray Industries, Inc. Composition de résine de polyaryléthercétone, matériau de base de résine renforcé par des fibres, et article moulé
US12202970B2 (en) 2018-11-08 2025-01-21 Shpp Global Technologies B.V. Thermoplastic composition, electrical wire and article comprising the electrical wire

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5532203B2 (ja) * 2009-06-03 2014-06-25 日産化学工業株式会社 接着剤組成物
KR101929835B1 (ko) * 2010-08-10 2018-12-18 닛산 가가쿠 가부시키가이샤 방향족 폴리에테르 유도체를 함유하는 접착제 조성물
JP5790945B2 (ja) * 2010-08-10 2015-10-07 日産化学工業株式会社 炭素と炭素の多重結合を有する樹脂を含む接着剤組成物

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US3712932A (en) * 1970-08-21 1973-01-23 Rhone Poulenc Sa Polysulphone compositions
US4026876A (en) * 1975-01-20 1977-05-31 Ciba-Geigy Corporation Soluble polyamide-imides derived from phenylindane diamines
US4142870A (en) * 1976-07-01 1979-03-06 Abrasives International N.V. Abrasive articles prepared from crosslinked aromatic polyimides
US4224214A (en) * 1978-07-25 1980-09-23 Standard Oil Company (Indiana) Injection molding of amic acid and amide-imide polymers and molding compositions
US4250279A (en) * 1979-12-26 1981-02-10 Union Carbide Corporation Polyarylate blends with polyetherimides
US4468506A (en) * 1982-04-02 1984-08-28 General Electric Company Polyetherimide blends

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US3712932A (en) * 1970-08-21 1973-01-23 Rhone Poulenc Sa Polysulphone compositions
US4026876A (en) * 1975-01-20 1977-05-31 Ciba-Geigy Corporation Soluble polyamide-imides derived from phenylindane diamines
US4142870A (en) * 1976-07-01 1979-03-06 Abrasives International N.V. Abrasive articles prepared from crosslinked aromatic polyimides
US4224214A (en) * 1978-07-25 1980-09-23 Standard Oil Company (Indiana) Injection molding of amic acid and amide-imide polymers and molding compositions
US4250279A (en) * 1979-12-26 1981-02-10 Union Carbide Corporation Polyarylate blends with polyetherimides
US4468506A (en) * 1982-04-02 1984-08-28 General Electric Company Polyetherimide blends

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5286812A (en) * 1988-02-19 1994-02-15 University Of Massachusetts High performance blends of aromatic polyimides with aromatic polyethersulfones
US5134202A (en) * 1988-12-30 1992-07-28 Amoco Corporation Process for miscible blends of imide containing polymers with poly(aryl sulfones)
EP0414124A3 (en) * 1989-08-19 1992-01-22 Hoechst Aktiengesellschaft Multicomponent alloy with a glass transition temperature
WO1994005404A1 (fr) * 1992-09-02 1994-03-17 L'air Liquide Societe Anonyme Pour L'etude Et L'ex Membranes de separation de gaz fabriquees a partir de melanges depolymeres de polyimide, de polyamide ou de polyamideimide aromatiques
US5494996A (en) * 1993-01-21 1996-02-27 Mitsui Toatsu Chemicals Inc. Polyimide resin composition
US5412065A (en) * 1993-04-09 1995-05-02 Ciba-Geigy Corporation Polyimide oligomers
EP0626412A1 (fr) * 1993-04-09 1994-11-30 Ciba-Geigy Ag Oligomères de polyimide
EP0636661A1 (fr) * 1993-07-28 1995-02-01 MITSUI TOATSU CHEMICALS, Inc. Composition de resine de polyimide
EP0778077A3 (fr) * 1995-12-07 1998-01-14 Sakellaropoulos, George Membranes polymères préparées à partir de mélanges de polysulfones et de polyimides pour la séparation de mélanges de gaz industriels
US20170362379A1 (en) * 2014-12-12 2017-12-21 Solvay Specialty Polymers Usa, Llc Poly(aryl ether) compositions for polymer-metal junctions and polymer-metal junctions and corresponding fabrication methods
US10519277B2 (en) * 2014-12-12 2019-12-31 Solvay Specialty Polymers Usa, Llc Poly(aryl ether) compositions for polymer-metal junctions and polymer-metal junctions and corresponding fabrication methods
EP3487904A4 (fr) * 2016-07-25 2020-06-10 The Boeing Company Résine époxy
US11718707B2 (en) 2016-07-25 2023-08-08 The Boeing Company Epoxy resin
US12202970B2 (en) 2018-11-08 2025-01-21 Shpp Global Technologies B.V. Thermoplastic composition, electrical wire and article comprising the electrical wire
EP4105273A4 (fr) * 2020-02-13 2024-06-26 Toray Industries, Inc. Composition de résine de polyaryléthercétone, matériau de base de résine renforcé par des fibres, et article moulé

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JPS62501370A (ja) 1987-06-04
EP0207981A4 (fr) 1987-07-06
EP0207981A1 (fr) 1987-01-14

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