EP0392008A1 - Copolymeres contenant des fractions de polybenzoxazole, polybenzothiazole et polybenzimidazole - Google Patents

Copolymeres contenant des fractions de polybenzoxazole, polybenzothiazole et polybenzimidazole

Info

Publication number
EP0392008A1
EP0392008A1 EP89912725A EP89912725A EP0392008A1 EP 0392008 A1 EP0392008 A1 EP 0392008A1 EP 89912725 A EP89912725 A EP 89912725A EP 89912725 A EP89912725 A EP 89912725A EP 0392008 A1 EP0392008 A1 EP 0392008A1
Authority
EP
European Patent Office
Prior art keywords
aromatic
group
block
thermoplastic
pbz
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP89912725A
Other languages
German (de)
English (en)
Other versions
EP0392008A4 (en
Inventor
William J. Harris
Wen-Fang Hwang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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
Priority claimed from US07/256,338 external-priority patent/US5089568A/en
Priority claimed from US07/327,925 external-priority patent/US5030706A/en
Priority claimed from US07/378,360 external-priority patent/US5110894A/en
Priority claimed from US07/407,973 external-priority patent/US5151489A/en
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Publication of EP0392008A1 publication Critical patent/EP0392008A1/fr
Publication of EP0392008A4 publication Critical patent/EP0392008A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/18—Polybenzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/22—Polybenzoxazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/32—Polythiazoles; Polythiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another

Definitions

  • thermoplastic polymer (1) a thermoplastic polymer containing
  • electron-deficient carbon groups are preferably chlorine, bromine or iodine and more preferably chlorine.
  • BB-monomers contain two o-amino- -basic moieties
  • AA-monomers contain two electron- -deficient carbon groups
  • AB-monomers contain an electron-deficient carbon group and an o-amino-basic moiety.
  • the electron-deficient carbon group, decoupling group and aromatic group have the meaning and preferred embodiments previously defined.
  • the decoupling group highly preferably comprises two aromatic groups and one ether or thioether moiety. It more highly preferably further comprises a second ether or thioether moiety.
  • Each AN-monomer preferably conforms to Formula 7(a):
  • Linear BB-monomers have the definition and preferred embodiments previously given, but comply with the following additional limitations:
  • Polyamide polymer units preferably further comprise:
  • Polyamides and their copolymers are prepared by a number of processes familiar to persons of ordinary skill in the art, such as by the reaction of an amine- -bearing monomer with a monomer bearing an acid group, or by the reaction of a carboxylic acid-bearing monomer and an isocyanate-bearing monomer, or by the reaction of formaldehyde with a dinitrile.
  • Such syntheses are described in numerous sources such as: 11 Encyclopedia of Poly. Sci. and Eng., Polyamides, 319 etseq. (John
  • Polyimide terminated by an active end group can be synthesized by methods obvious to a person of ordinary skill in the art.
  • Polyimide terminated by an acid anhydride moiety can be converted to polyimide terminated by an acid group suitable to serve as an electron deficient carbon group either by hydrolyzing the anhydride or by contacting it with an amino acid such as p-aminobenzoic acid under reaction conditions.
  • Polyimide terminated by an active aromatic group is synthesized by contacting anhydride-terminated polyimide with a monomer comprising an amine group and two decoupled aromatic groups, such as phenoxyaniline.
  • Poly(aromatic ketone), poly(aromatic sulfone) poly(aromatic ether) and copolymer blocks used in the present invention are preferably terminated by active end groups comprising an acid group, an aromatic group which functions as an acylation reactive group, or an electron-deficient carbon group.
  • Poly(aromatic ether) etc. terminated by an acid group can be synthesized by using excess EE-monomer, and that terminated by an aromatic group can be synthesized by using excess NN-monomer.
  • monomer is chosen such that the acid group or aromatic moiety which terminates the polymer is linked to the polymer chain by a decoupling group.
  • At least two primary monomers are used in the process, and each primary monomer contains at least two functional moieties chosen from the group consisting of azole-forming moieties and acylation reactive groups. At least two of the primary monomers must contain azole- -forming moieties which can react to form an azole ring. At least two of the primary monomers must contain acylation reactive groups which can react to form an aromatic ketone or sulfone moiety. At least one of the primary monomers must contain a first functional moiety which can react as an azole-forming moiety and a second functional moiety which can react as an acylation reactive group .
  • the decoupling groups and/or divalent organic moieties of the monomers may contain units ordinarily associated with other polymers, such as amide, imide or other moieties which are stable in the acid and do not interfere with the condensation of the monomers.
  • Copolymerizations may optionally be carried out using only two monomers. Suitable two monomer reactions comprise the reaction of AN-monomer and BE-monomer or the reaction of AE-monomer and BN-monomer. The two monomer reactions preferably conform to one of Formula 33(a)-(b):
  • the copolymerization preferably utilizes reactions of AE-, BE- and NN-monomers as illustrated le Formula 34(a); AN-, DN- and EE-monomers as illustrated in Formula 34(c); or AN-, BB- and EE-monomers as illustrated in Formula 34(d).
  • Preferred reactions more preferably conform to one of Formulae 35(a)-(d)
  • the copolymer has the structure of Formula 35(b) wherein b averages 2. If the molar ratio of oxy-bis- -(4-benzoic acid) to BB-monomer is greater than 2:1, the copolymer may average less than one benzazole unit per mer unit (b is on average less than 1).
  • benzoxaiole moiety in a position wherein it remains sufficiently active to react in a
  • Intermediate EE-monomers more preferably comprise:
  • thermoplastic polymer is preferably polyamide, polyquinoxaline, poly(aromatic ether) or a copolymer thereof. It is more preferably polyamide or a copolymer thereof.
  • the weight ratio of polymers used in the reaction has the same limits and preferred embodiments as the weight ratio of thermoplastic blocks and PBZ blocks within the product block eopolymer. More preferably, the molar quantities ef the two polymers are such that substantially all PBZ polymer is part of a block copolymer. Most preferably, the two polymers are also used in equimolar quantities or the thermoplastic polymer is in a molar excess.
  • Polymer compositions or block copolymers of the present invention can be formed into powders by known methods, such as coagulation in a blender followed by grinding. Alternatively, they may be extruded as fibers and films, as described hereinafter. Isolated block copolymer can be added to homopolymer and mixtures thereof as a compatibilizing agent. Fabrication and Physical Properties of Items Using Polymer Compositions of the Present Invention
  • Polymer compositions and block copolymers of the present invention and articles formed from them are preferably thermoplastic, although the glass transition temperature varies substantially depending upon the chemical composition of the block copolymer and the polymer composition. Desirable glass transition temperatures also vary depending upon the proposed use for the polymer. Under ordinary circumstances, the glass transition temperature is preferably no more than about 400°C, more preferably no more than about 350°C, more highly preferably no more than about 300°C and most preferably no more than about 280°C. Under ordinary circumstances, the glass transition temperature is preferably at least about 100°C, more preferably at least about 200°C, and most preferably at least about 250°C.
  • a 25.00-g portion of dope was added containing polyphosphoric acid and about 14 weight percent cis-PBO polymer which was made as described in Example 1 and had an inherent viscosity of 6.1 dL/g in methanesulfonic acid at 25°C and a concentration of 0.05 g/dL.
  • the reaction was continued for 48 hours at 90°C, and then cooled to 50°C.
  • a 0.57-g (2.18 mmoles) portion of 1,4--diphenoxybenzene was added, followed by 88.60 g of 10-1 methanesulfonic acid solution added in two portions 30 minutes apart. The reaction was continued at 50°C for 72 hours.
  • An aryl-aliphatic polyamide terminated by active end groups was synthesized by the following procedure.
  • a mixture of 10.06 g (47.2 mmoles) of isophthaloyl dichloride and 1.80 g (5.56 mmoles) of phenoxyphenoxybenzoyl chloride from Example C was dissolved in 100 ml of methylene chloride.
  • a mixture of 5.81 g (50.0 mmoles) of hexamethylenediamine and 10.6 g (100 mmoles) of anhydrous sodium carbonate was dissolved in 250 ml of deionized water.
  • the second mixture was stirred rapidly and the first mixture was added.
  • the mixture was stirred for 10 minutes, and the resulting aryl-aliphatic polyamide was filtered.
  • the polyamide was washed with water 5 times and dried under vacuum at 100°C.
  • the recovered polyamide weighs 12.27 g. It had an inherent viscosity of 0.90 dL/g in m-cresol

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

On peut former des copolymères blocs à partir de polymères hétérocycliques tels que le polybenzoxazole et de polymères thermoplastiques tels que la polyamide ou le poly(cétone éther aromatique). Les compositions de copolymères blocs sont thermoplastiques et ne présentent aucune séparation de phase notable, même à des températures approchant leur température de transition vitreuse. On peut donner à ces compositions de copolymères blocs des formes de fibres, de feuilles ou de stratifiés ou d'objets façonnés par compression. Les polymères polybenzoxazoles, polybenzothiazoles et polybenzimidazoles terminés par un anneau aromatique actif ou des groupes acylatiques se prêtent particulièrement bien à la préparation de ces copolymères blocs.
EP19890912725 1988-10-11 1989-10-06 Copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties Withdrawn EP0392008A4 (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US256338 1981-04-22
US407973 1982-08-13
US07/256,338 US5089568A (en) 1988-10-11 1988-10-11 Process of making thermoplastic copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties
US07/327,925 US5030706A (en) 1988-10-11 1989-03-23 Copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties
US327925 1989-03-23
US07/378,360 US5110894A (en) 1988-10-11 1989-07-07 Copolymers containing polybenzazole mer units and poly(aromatic ketone) or poly(aromatic sulfone) mer units
US07/407,973 US5151489A (en) 1988-10-11 1989-09-15 Copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties
US378360 2003-03-03

Publications (2)

Publication Number Publication Date
EP0392008A1 true EP0392008A1 (fr) 1990-10-17
EP0392008A4 EP0392008A4 (en) 1991-09-04

Family

ID=27500568

Family Applications (2)

Application Number Title Priority Date Filing Date
EP19890912725 Withdrawn EP0392008A4 (en) 1988-10-11 1989-10-06 Copolymers containing polybenzoxazole, polybenzothiazole and polybenzimidazole moieties
EP89118821A Expired - Lifetime EP0368006B1 (fr) 1988-10-11 1989-10-10 Copolymères contenant des séquences de polybenzoxazole, polybenzothiazole et polybenzimidazole

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89118821A Expired - Lifetime EP0368006B1 (fr) 1988-10-11 1989-10-10 Copolymères contenant des séquences de polybenzoxazole, polybenzothiazole et polybenzimidazole

Country Status (6)

Country Link
EP (2) EP0392008A4 (fr)
JP (1) JPH03501751A (fr)
KR (1) KR930006927B1 (fr)
CA (1) CA2000455A1 (fr)
DE (1) DE68922067T2 (fr)
WO (1) WO1990003995A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5273823A (en) * 1988-10-11 1993-12-28 The Dow Chemical Company Shaped articles containing copolymers of polybenzazoles
US5217809A (en) * 1990-08-06 1993-06-08 The Dow Chemical Company Shaped articles containing copolymers of polybenzazoles
US5091500A (en) * 1990-09-21 1992-02-25 The Dow Chemical Company Polybenzazole polymer containing perfluorocyclobutane rings
DE4030511A1 (de) * 1990-09-27 1992-04-02 Basf Ag Hochtemperaturbestaendige, benzthiazolhaltige polyarylether
US5194568A (en) * 1990-10-19 1993-03-16 The Dow Chemical Company Staged polymerization of polybenzazole polymers
US5089591A (en) * 1990-10-19 1992-02-18 The Dow Chemical Company Rapid advancement of molecular weight in polybenzazole oligomer dopes
US5248721A (en) * 1991-03-13 1993-09-28 The Dow Chemical Company Prepregs containing a fiber and a thermoplastic polybenzazole copolymer matrix
US5210257A (en) * 1991-04-12 1993-05-11 The Dow Chemical Company Preparation of aryl compounds containing carboxyl and sulfonyl groups
AT400144B (de) * 1992-02-06 1995-10-25 Chemie Linz Gmbh Amidoimidobisphenole, deren herstellung und daraus abgeleitete thermostabile polymere
US5266677A (en) * 1992-05-27 1993-11-30 University Of North Carolina At Chapel Hill Thiophene-based polymers
US5367042A (en) * 1992-08-27 1994-11-22 The Dow Chemical Company Process for fabricating oriented polybenzazole films
JP2005023217A (ja) * 2003-07-03 2005-01-27 Toyobo Co Ltd ポリベンザゾール系フィルムおよびその製造法
JP2010525183A (ja) * 2007-04-30 2010-07-22 テイジン・アラミド・ビー．ブイ． ポリベンザゾールおよびポリベンザゾール前駆体
CN106588703B (zh) * 2016-10-26 2018-06-29 山东天一化学股份有限公司 一种高纯度的4,4’-氧代双苯磺酰氯的制备方法
CN117317374B (zh) * 2023-11-30 2024-02-02 蓝固(淄博)新能源科技有限公司 一种电解液添加剂、其制备方法、电解液和二次电池

Citations (3)

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Publication number Priority date Publication date Assignee Title
US3671491A (en) * 1969-03-26 1972-06-20 Celanese Corp Random benzimidazole-benzoxazole copolymers and methods of preparation
US4079039A (en) * 1974-03-04 1978-03-14 Horizons Research Incorporated Polyheterocyclic polymers derived from substituted tetraamino pyridines
EP0178185A2 (fr) * 1984-10-11 1986-04-16 RAYCHEM CORPORATION (a Delaware corporation) Polymères aromatiques

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US3763210A (en) * 1971-01-20 1973-10-02 Gen Electric Arloxy and arylthio nitrite compositions
JPS50127996A (fr) * 1974-03-29 1975-10-08
US4229566A (en) * 1979-08-24 1980-10-21 The United States Of America As Represented By The Secretary Of The Air Force Articulated para-ordered aromatic heterocyclic polymers containing diphenoxybenzene structures
US4414383A (en) * 1982-05-24 1983-11-08 Celanese Corporation High molecular weight polybenzimidazole preparation with phosphorus containing polymerization catalyst
US4533693A (en) * 1982-09-17 1985-08-06 Sri International Liquid crystalline polymer compositions, process, and products
DE3390220C2 (de) * 1982-09-17 1995-04-20 Dow Chemical Co Flüssigkristalline Polymerzusammensetzungen, Verwendungen und Produkte
US4463167A (en) * 1983-03-21 1984-07-31 Celanese Corporation Two stage high molecular weight polybenzimidazole production with phosphorus containing catalyst
JPS60181128A (ja) * 1984-02-29 1985-09-14 Sumitomo Bakelite Co Ltd 耐熱性樹脂組成物
US4703103A (en) * 1984-03-16 1987-10-27 Commtech International Liquid crystalline polymer compositions, process and products
US4544713A (en) * 1984-05-16 1985-10-01 The United States Of America As Represented By The Secretary Of The Air Force Method for making heterocyclic block copolymer
US4973630A (en) * 1986-02-19 1990-11-27 Hoechst Celanese Corp. Compositions of aromatic polybenzimidazoles and aromatic polyetherimides
EP0240302A2 (fr) * 1986-04-01 1987-10-07 Celanese Corporation Compositions de polybenzimidazole aromatique et de polyimide aromatique et procédé de préparation
CA1312261C (fr) * 1987-05-22 1993-01-05 Francis Plomb Machine-outil
JPH086030B2 (ja) * 1987-06-25 1996-01-24 本田技研工業株式会社 剛直芳香族ポリマ−の分子複合材の製造方法
JPH0826219B2 (ja) * 1987-06-25 1996-03-13 本田技研工業株式会社 剛直芳香族ポリマ−の分子複合材の製造方法
JPH01202712A (ja) * 1988-02-09 1989-08-15 Nec Ic Microcomput Syst Ltd レンズ絞り
JPH0678440B2 (ja) * 1988-05-16 1994-10-05 工業技術院長 高分子複合体の製造法

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Publication number Priority date Publication date Assignee Title
US3671491A (en) * 1969-03-26 1972-06-20 Celanese Corp Random benzimidazole-benzoxazole copolymers and methods of preparation
US4079039A (en) * 1974-03-04 1978-03-14 Horizons Research Incorporated Polyheterocyclic polymers derived from substituted tetraamino pyridines
EP0178185A2 (fr) * 1984-10-11 1986-04-16 RAYCHEM CORPORATION (a Delaware corporation) Polymères aromatiques

Non-Patent Citations (1)

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Title
See also references of WO9003995A1 *

Also Published As

Publication number Publication date
KR900701899A (ko) 1990-12-05
KR930006927B1 (ko) 1993-07-24
CA2000455A1 (fr) 1990-04-11
EP0368006A2 (fr) 1990-05-16
DE68922067D1 (de) 1995-05-11
DE68922067T2 (de) 1995-10-26
EP0368006B1 (fr) 1995-04-05
JPH03501751A (ja) 1991-04-18
WO1990003995A1 (fr) 1990-04-19
EP0368006A3 (fr) 1991-03-27
EP0392008A4 (en) 1991-09-04

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