EP0226637A1 - Poly(arylether-cetones) a chaine etendue - Google Patents

Poly(arylether-cetones) a chaine etendue

Info

Publication number
EP0226637A1
EP0226637A1 EP19860904997 EP86904997A EP0226637A1 EP 0226637 A1 EP0226637 A1 EP 0226637A1 EP 19860904997 EP19860904997 EP 19860904997 EP 86904997 A EP86904997 A EP 86904997A EP 0226637 A1 EP0226637 A1 EP 0226637A1
Authority
EP
European Patent Office
Prior art keywords
carbonate
bicarbonate
aryl ether
chain
bis
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Withdrawn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
EP19860904997
Other languages
German (de)
English (en)
Inventor
Robert Andrew Clendinning
George Thomas Kwiatkowski
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.)
BP Corp North America Inc
Original Assignee
BP Corp North America Inc
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 BP Corp North America Inc filed Critical BP Corp North America Inc
Publication of EP0226637A1 publication Critical patent/EP0226637A1/fr
Withdrawn legal-status Critical Current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
    • 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
    • C08G65/48—Polymers modified by chemical after-treatment
    • 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

Definitions

  • PAEK is the acronym of poly(aryl ether ketone)
  • PEEK is the acronym of poly(ether ether ketone) in which the 1,4-phenylene units in the structure are assumed.
  • PAEK's may be produced by the Frledel-Crafts catalyzed reaction of aromatic diacylhalldes with unsubstltuted aromatic compounds such as dlphenyl ether as described in, for example, U.S. Patent No. 3,065,205. These processes are generally inexpensive processes; however, the polymers produced by these processes have been stated by Dahl et al., supra, to be brittle and thermally unstable. The Dahl patents, supra, allegedly depict more expensive processes for making superior PAEK's by Frledel-Crafts catalysis. In contrast, PAEK's such as PEEK made by nucleophlllc aromatic substitution reactions generally display good toughness and acceptable mechanical properties.
  • the present invention is directed to chain extended poly(aryl ether ketone) polymers. Both the preparation of the starting poly(aryl ether ketone) segments and their subsequent coupling with a diphenol are performed via the nucleophlllc route, i.e. using a base and an aprotic solvent. Products having superior toughness, good fabricabillty, and excellent solvent and temperature resistance are obtained.
  • Fluorine and chlorine substituted benzenold reactants are preferred; the fluorine compounds for fast reactivity and the chlorine compounds for their inexpenslveness. Fluorine substituted benzenold compounds are most preferred, particularly when there is a trace of water present in the polymerization reaction system. However, this water content should be maintained below about 11 and preferably below 0.5% for best results.
  • Examples of specific dihydric polynuclear phenols include among others the bis-(hydroxyphenyl) alkanes such as 2,2-bis-(4-hydroxyphenyl)propane, 2,4'-dihydroxydiphenylmethane, bis-(2-hydroxypheny1)methane, bis-(4-hydroxyphenyl)methane, bis(4-hydroxy-2,6-dlmethyl-3-methoxyphenyl)methane, 1,1-bls-(4-hydroxyphenyl)ethane, 1,2-bis-(4-hydroxyphenyl)ethane, 1,1-bis-(4-hydroxy-2-chloro ⁇ henyl)ethane, 1,1-bis-(3-methyl-4-hydroxyphenyl)propane, 1,3-bis-(3-methyl-4-hydroxyphenyl)pro ⁇ ane, 2,2-bis-(3-phenyl-4-hydroxyphenyl) ⁇ ro ⁇ ane, 2,2-bis-(3-isopro ⁇ yl-4-hydroxyphen
  • the polymerization reaction may be terminated by mixing a suitable end capping reagent, e.g. a mono or polyfunctional halide such as methyl chloride, t-butyl chloride or
  • the sodium carbonate or bicarbonate and potassium fluoride are used such that the ratio of potassium to sodium therein is from about 0.001 to about 0.5, preferably from about 0.01 to about 0.25, and most preferably from about 0.02 to about 0.20.
  • An excess of total alkali metal may be employed. Hence there may be about 1 to about 1.7 atoms of alkali metal per phenol group. While the use of a large excess of alkali metal may give rise to faster reactions, there is the attendant risk of cleavage of the resulting polymer, particularly when using high temperatures and/or the more active alkali metal salts.
  • cesium is a more active metal and potassium is a less active metal so that less cesium and more potassium are used.
  • the chioride salts are less active than the fluoride salts so that more chloride and less fluoride is used.
  • the polymers of this invention may include mineral fillers such as carbonates including chalk, calcite and dolomite; silicates including mica, talc, wollastonite; silicon dioxide; glass spheres; glass powders; aluminum; clay; quartz; and the like. Also, reinforcing fibers such as fiberglass, carbon fibers, and the like may be used.
  • the polymers may also include additives such as titanium dioxide; thermal stabilizers, ultraviolet light stabilizers, plasticizers, and the like.
  • the oligomer was prepared essentially as in Example 1 except that less potassium fluoride (0.01465 moles, 0.85 gm) was used and the reaction mixture was heated at 200°C for 30 minutes, at 250°C for 1 hour, and then at 290°C for 2 hours.
  • the isolated oligomer had a reduced viscosity of 0.51 dl/gm (concentrated sulfuric acid, lgm/100 ml at 25°C).
  • Example 2 The reaction of Example 2 was repeated using twice the amounts of all ingredients (500 ml flask). After heating at 290°C for 2 hours,
  • the polymer had a reduced viscosity of 1.02 as measured in concentrated sulfuric acid at 25°C at 1% concentration.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyethers (AREA)

Abstract

Nouvelles poly(aryléther-cétones) cristallines à chaîne étendue présentant une excellente résistance mécanique, une excellente aptitude au façonnage ainsi qu'une très bonne résistance aux solvants et aux températures élevées.
EP19860904997 1985-06-12 1986-05-01 Poly(arylether-cetones) a chaine etendue Withdrawn EP0226637A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74395785A 1985-06-12 1985-06-12
US743957 1985-06-12

Publications (1)

Publication Number Publication Date
EP0226637A1 true EP0226637A1 (fr) 1987-07-01

Family

ID=24990857

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19860904997 Withdrawn EP0226637A1 (fr) 1985-06-12 1986-05-01 Poly(arylether-cetones) a chaine etendue

Country Status (4)

Country Link
EP (1) EP0226637A1 (fr)
JP (1) JPS63500871A (fr)
CA (1) CA1270993A (fr)
WO (1) WO1986007368A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4829143A (en) * 1986-10-28 1989-05-09 Amoco Corporation Modified poly(aryl ether ketones) derived from biphenol
DE3700808A1 (de) * 1987-01-14 1988-07-28 Basf Ag Verfahren zur herstellung von polyaryletherketonen
US4777235A (en) * 1987-07-01 1988-10-11 Amoco Corporation Production of polyarylene ether from activated dihalo benzenoid monomer, dihydroxy benzenoid monomer and Bis(hydroxyphenyl) monomer
GB2237810A (en) * 1989-11-06 1991-05-15 Ici Plc Aromatic polyetherketones
GB0020620D0 (en) * 2000-08-22 2000-10-11 Cytec Tech Corp Compostions adapted for chain linking
CN100389138C (zh) * 2006-03-28 2008-05-21 吴忠文 以环丁砜为溶剂合成聚醚醚酮树脂的方法
CN100374483C (zh) * 2006-03-29 2008-03-12 长春吉大高科技股份有限公司 聚醚醚砜和聚醚醚酮三元共聚物的制备方法
RU2494118C1 (ru) * 2012-03-20 2013-09-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования Кабардино-Балкарский государственный университет им. Х.М. Бербекова Способ получения полиэфиркетонов

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1504194A (en) * 1975-03-25 1978-03-15 Ici Ltd Aromatic polymer manufacture
DE2861696D1 (en) * 1977-09-07 1982-04-29 Ici Plc Thermoplastic aromatic polyetherketones, a method for their preparation and their application as electrical insulants
US4275186A (en) * 1978-07-27 1981-06-23 Union Carbide Corporation Oligomer extended polyarylethers
US4339568A (en) * 1979-12-03 1982-07-13 Union Carbide Corporation Aromatic polymers containing ketone groups
DE3014230A1 (de) * 1980-04-14 1981-10-22 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von ketogruppenhaltigen polyaethern
EP0125816B1 (fr) * 1983-05-12 1987-09-23 Imperial Chemical Industries Plc Procédé pour élever le poids moléculaire de poly(éthers d'aryle)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8607368A1 *

Also Published As

Publication number Publication date
CA1270993A (fr) 1990-06-26
WO1986007368A1 (fr) 1986-12-18
JPS63500871A (ja) 1988-03-31

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Inventor name: KWIATKOWSKI, GEORGE, THOMAS

Inventor name: CLENDINNING, ROBERT, ANDREW