EP0000904A1 - Récupération de polycarbonates de haute valeur à partir de déchets de polycarbonates - Google Patents

Récupération de polycarbonates de haute valeur à partir de déchets de polycarbonates Download PDF

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Publication number
EP0000904A1
EP0000904A1 EP78100635A EP78100635A EP0000904A1 EP 0000904 A1 EP0000904 A1 EP 0000904A1 EP 78100635 A EP78100635 A EP 78100635A EP 78100635 A EP78100635 A EP 78100635A EP 0000904 A1 EP0000904 A1 EP 0000904A1
Authority
EP
European Patent Office
Prior art keywords
polycarbonate
hydroxyphenyl
bis
saponification
polycarbonates
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.)
Granted
Application number
EP78100635A
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German (de)
English (en)
Other versions
EP0000904B1 (fr
Inventor
Karsten Dr. Idel
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.)
Bayer AG
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Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0000904A1 publication Critical patent/EP0000904A1/fr
Application granted granted Critical
Publication of EP0000904B1 publication Critical patent/EP0000904B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/40—Post-polymerisation treatment

Definitions

  • the present invention relates to a process for the recovery of aromatic, high molecular weight, thermoplastic polycarbonates from polycarbonate waste, the polycarbonate waste being present both purely as a transparent natural material and also together with organic and in particular inorganic dyes and / or other additives or as an alloy in combination with other thermoplastic materials can.
  • E. Bullack for example, in the GDR 45575, 46282, 45599, 45600 and 46353 describes processes for processing polycarbonates, in particular with a view to extraction of 4,4'-dioxy-diaryl-alkanes as starting substances for the polycarbonate synthesis.
  • the 4,4'-dioxy-diarylalkanes are cleaved by means of alcohols, acid anhydrides or small amounts of basic catalysts according to some. receive complex cleaning procedures.
  • the cleavage is achieved by adding phenols or diaryl carbonates in the presence of metal oxide catalysts and temperatures above 180 ° C. At these temperatures, especially in the presence of metal oxide catalysts, there is a risk of side reactions, and extensive cleaning operations are necessary to obtain clean starting substances.
  • polycarbonates are saponified gently both in pure or colored form and as polymer alloys in a smooth one-pot reaction and, if appropriate after filtering off additives, dyes, etc. or alloy components, immediately afterwards in a smooth one-pot reaction in the same reaction media to high-molecular, thermoplastic and can dissolve soluble polycarbonates.
  • polycarbonates were thus cleaved and the reaction mixture remaining after the cleavage was directly converted back to the polycarbonate synthesis by the phase interface method without any intermediate purification. After adding a solvent which is not miscible with water and is customary in the phase interface condensation of polycarbonates, for example
  • Methylene chloride or chlorobenzene can be condensed directly by introducing phosgene without any intermediate cleaning.
  • the pH of the alkaline phase should be kept between 9 and 14 depending on the type of diphenol.
  • tertiary amines such as e.g. Triethylamine, tributylamine, N-alkylpiperidine or ammonium, sulfonium, phosphonium or arsonium compounds or nitrogen hetaryls such as pyridine are used.
  • the monohydric phenols present at the chain end in polycarbonates are found as cleavage products after the saponification step in the alkaline reaction medium and, during or after the phosgenation, are fully incorporated again as chain limiters, so that the resynthesized polycarbonates achieve the same solution viscosity as the polycarbonate wastes converted as starting material. If other solution viscosities are to be set, an additional amount of free bisphenol can be added for a desired higher solution viscosity and an additional amount of monohydric phenol can be added for a lower solution viscosity.
  • condensed compounds with more than two condensable functional groups such as e.g. Tris or tetraphenols, which are incorporated as branching agents in polycarbonates, are completely incorporated again in the resynthesis of the polycarbonates.
  • a change in the branching concentration in the recovered polycarbonate is again possible by adding an additional amount of branching agent or free bisphenol to the reaction medium before the phosgenation.
  • the present invention thus provides a process for the recovery of aromatic, high molecular weight, thermoplastic polycarbonates from polycarbonate waste, which is characterized in that it saponifies the polycarbonate waste in bulk or in solution at temperatures between 25 0 C and 2200C, separated from unsaponifiable matter and then the saponification mixture is phosgenated and polycondensed without further purification and workup steps using the methods of two-phase interfacial polycondensation.
  • Polycarbonate waste is understood to mean all polycarbonate plastic articles that are no longer usable, but also the residues, waste products, waste, etc. that are produced during the manufacture and deformation of the polycarbonate plastic.
  • aromatic polycarbonates which can be worked up as polycarbonate wastes can also be incorporated by incorporation of small amounts, preferably amounts between 0.05 and 2.0 mol% (based on diphenols used), of three- or more than three-functional compounds, in particular those with three or more be branched as three phenolic hydroxyl groups, for example by incorporating phloroglucin, 1,3,5-tri- (4-hydroxyphenyl) benzene, 1,1,1-tri- (4-hydroxyphenyl) ethanol or 1, 4-bis (4,4'-dihydroxytriphenylmethyl) benzene.
  • the aromatic polycarbonates which can be worked up as polycarbonate wastes generally have average weight-average molecular weights Mw of 10,000 to more than 200,000, preferably 20,000 to 80,000, determined by measuring the rel. Viscosity in CH 2 C1 2 at 25 ° C and a concentration of 0.5% by weight.
  • the molecular weights of the polycarbonates can be regulated in a customary manner, for example by incorporating phenol, tribromophenol or p-tert-butylphenol.
  • polycarbonates that can be processed as polycarbonate waste can also be present as mixtures of different polycarbonates, for example mixed with fractions of low molecular weight polycarbonates, or also as polymer alloys, for example with polymers or copolymers based on styrene, styrene-acrylonitrile, acrylonitrile-butadiene-styrene or butadiene rubber.
  • the saponification of the polycarbonate waste takes place in bulk or in solution, the solvents used being the customary solvents, such as methylene chloride or chlorobenzene, which are suitable for polycarbonate production by the two-phase interface process.
  • the solvents used being the customary solvents, such as methylene chloride or chlorobenzene, which are suitable for polycarbonate production by the two-phase interface process.
  • the saponification takes place in a neutral, preferably alkaline, aqueous reaction medium, the saponification in substance being heterogeneous and the saponification in solution at the interface of the two-phase system, the latter proceeding more cheaply and more rapidly.
  • aqueous reaction medium preferably between 25 and 100 moles of water per mole of polycarbonate structural unit to be saponified are used.
  • the basic saponification agents used are, for example, sodium hydroxide, potassium hydroxide, calcium oxide, preferably sodium hydroxide.
  • the saponification takes place at temperatures between 25 ° and 220 ° C and, if appropriate, using excess pressure up to preferably 100 atmospheres.
  • Phosphites or phosphines can also be added as catalysts. If the polycarbonate waste contains unsaponifiable constituents such as lubricants, stabilizers, pigments, dyes, fillers such as glass powder, quartz products, graphite, molybdenum sulfide, metal powder, powder of high-melting plastics such as polytetraethylene powder, natural fibers such as asbestos, and also glass fibers of various types, metal threads, etc., these become after filtration in a known manner, for example by filtration.
  • unsaponifiable constituents such as lubricants, stabilizers, pigments, dyes, fillers such as glass powder, quartz products, graphite, molybdenum sulfide, metal powder, powder of high-melting plastics such as polytetraethylene powder, natural fibers such as asbestos, and also glass fibers of various types, metal threads, etc.
  • the one- or two-phase solutions resulting from the saponification of the polycarbonate wastes can be used directly for the polycarbonate production according to the interfacial process, optionally adding the customary polycarbonate solvents such as methylene chloride or chlorobenzene and the pH of the aqueous solution between 9 and 14 is set.
  • the customary polycarbonate solvents such as methylene chloride or chlorobenzene
  • the subsequent phosgenation is usually carried out at room temperature, a quantity of phosgene of 1 to 3 mol, based on 1 mol of diphenol, preferably being used.
  • the duration of phosgenation is a maximum of 1 hour.
  • Tertiary amines or other polycondensation catalysts are added in amounts between 0.01 and 10 mol%, based on the moles of diphenols, before or in particular after the phosgenation.
  • the polycondensation then takes place in the usual manner at temperatures between 20 ° and 40 ° C and, depending on the diphenol used, is complete after a period of 1-5 hours.
  • the polycarbonate solutions obtained are worked up as usual and the polycarbonate is isolated in the customary manner.
  • the duration of saponification and the amount of base used are directly related. As the table below shows, the amount of caustic soda used can be at a cost extended saponification times can be reduced.
  • the saponification was carried out in the interface: 25.4 g of polycarbonate from Example 1 were dissolved in 300 ml of chlorobenzene and mixed with 15 N sodium hydroxide solution. The time until the polycarbonate was completely hydrolyzed was measured:
  • the saponification can also be carried out under pressure. 101.6 g of polycarbonate from Example 1, 400 ml of dist. Water and 2.26 g of 45% sodium hydroxide solution are heated in an autoclave to 210 ° C. at 50 bar pressure in 1 hour and held there for 2 hours. The mixture obtained is mixed with 840 g of 6.2% sodium hydroxide solution and 1500 ml of methylene chloride. While maintaining a pH of 13-14, 60 g of phosgene are introduced in 1 h and then condensed for 1 h after the addition of 6 ml of 4% aqueous triethylamine. The reaction mixture is worked up according to Example 1.
  • the polycarbonate shows the same property profile as a polycarbonate of corresponding chain length, which was obtained by the usual condensation of bisphenol A and phosgene using the phase interface process.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
EP78100635A 1977-08-20 1978-08-09 Récupération de polycarbonates de haute valeur à partir de déchets de polycarbonates Expired EP0000904B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772737693 DE2737693A1 (de) 1977-08-20 1977-08-20 Wiedergewinnung hochwertiger polycarbonate aus polycarbonat-abfaellen
DE2737693 1977-08-20

Publications (2)

Publication Number Publication Date
EP0000904A1 true EP0000904A1 (fr) 1979-03-07
EP0000904B1 EP0000904B1 (fr) 1980-07-23

Family

ID=6016956

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100635A Expired EP0000904B1 (fr) 1977-08-20 1978-08-09 Récupération de polycarbonates de haute valeur à partir de déchets de polycarbonates

Country Status (5)

Country Link
US (1) US4212774A (fr)
EP (1) EP0000904B1 (fr)
JP (1) JPS6051499B2 (fr)
DE (2) DE2737693A1 (fr)
IT (1) IT1106890B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0086358A1 (fr) * 1982-02-06 1983-08-24 Bayer Ag Procédé de préparation de tétraméthylène carbonate et de bis-tétraméthylène dicarbonate
EP0355319A3 (fr) * 1988-07-11 1991-07-31 General Electric Company Procédé de récupération d'un phénol dihydrique à partir de déchets de polyester
EP0641758A3 (fr) * 1993-09-07 1995-05-24 Gen Electric Procédé de récupération de composés bis-hydroxy aromatiques et bis-arylcarbonates au départ de déchets de polycarbonates aromatiques.

Families Citing this family (32)

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DE2842004A1 (de) * 1978-09-27 1980-04-10 Bayer Ag Verfahren zur herstellung von modifizierten polycarbonat-formmassen
DE2928464A1 (de) * 1979-07-13 1981-01-29 Bayer Ag Verwendung von speziellen rohbisphenolen zur herstellung von polycarbonaten
US4451583A (en) * 1982-01-26 1984-05-29 Olin Corporation Recycling of flexible polyurethane foam scrap
DE4039024A1 (de) * 1990-09-21 1992-03-26 Bayer Ag Reinigung von polycarbonat- und polyestercarbonat-abfaellen
DE4220412C2 (de) 1992-06-22 1995-12-07 Bayer Ag Verfahren zum Spalten von Polycarbonaten in Bisphenole und Diarylcarbonate
US5340839A (en) * 1992-09-24 1994-08-23 General Electric Company Method for salvaging organic thermoplastic values from discarded surface treated organic thermoplastic substrates
US5306349A (en) * 1992-11-23 1994-04-26 Sony Music Entertainment, Inc. Method for removing coatings from compact discs
DE4240314A1 (de) 1992-12-01 1994-06-09 Bayer Ag Verfahren zur Herstellung von thermoplastischen Polycarbonaten
US5414021A (en) * 1993-08-02 1995-05-09 General Electric Company Method for salvaging aromatic polycarbonate blend values
JPH09194614A (ja) * 1996-01-25 1997-07-29 Matsushita Electric Ind Co Ltd プラスチック成形体、およびプラスチック成形体の処理方法
US5958987A (en) * 1996-04-10 1999-09-28 The Coca-Cola Company Process for separating polyester from other materials
AU3006999A (en) 1998-03-16 1999-10-11 American Commodities, Inc. Process for removing deleterious surface material from polymeric regrind particles
AUPQ747100A0 (en) * 2000-05-11 2000-06-08 Geo2 Limited Delamination process
US6436197B1 (en) 2000-09-05 2002-08-20 Metss Corporation Optical media demetallization process
WO2002102884A1 (fr) * 2001-06-19 2002-12-27 United Resource Recovery Corporation Procede relatif a la separation de polyester a partir d'autres materiaux
JP2005126358A (ja) * 2003-10-23 2005-05-19 Teijin Chem Ltd 廃芳香族ポリカーボネートから芳香族ジヒドロキシ化合物金属塩水溶液を得る方法
JP4571395B2 (ja) * 2003-12-03 2010-10-27 帝人化成株式会社 廃芳香族ポリカーボネートから芳香族ジヒドロキシ化合物を得る方法
JP2005162674A (ja) * 2003-12-03 2005-06-23 Teijin Chem Ltd 廃芳香族ポリカーボネートから芳香族ジヒドロキシ化合物を得る方法
JP2005179228A (ja) * 2003-12-18 2005-07-07 Teijin Chem Ltd 廃芳香族ポリカーボネート樹脂から芳香族ジヒドロキシ化合物を得る方法
JP4571398B2 (ja) * 2003-12-18 2010-10-27 帝人化成株式会社 廃芳香族ポリカーボネート樹脂から芳香族ジヒドロキシ化合物のアルカリ水溶液を得る方法
JP2005179267A (ja) * 2003-12-19 2005-07-07 Teijin Chem Ltd 廃芳香族ポリカーボネート樹脂から芳香族ジヒドロキシ化合物を得る方法
JP4550407B2 (ja) * 2003-12-19 2010-09-22 帝人化成株式会社 廃芳香族ポリカーボネート樹脂から芳香族ジヒドロキシ化合物のアルカリ水溶液を得る方法
JP4571413B2 (ja) * 2004-01-19 2010-10-27 帝人化成株式会社 廃芳香族ポリカーボネート樹脂から芳香族ジヒドロキシ化合物のアルカリ水溶液を得る方法
JP4571414B2 (ja) * 2004-01-20 2010-10-27 帝人化成株式会社 廃芳香族ポリカーボネート樹脂の分解により得られた芳香族ジヒドロキシ化合物のアルカリ水溶液の貯蔵方法
JP2005239562A (ja) * 2004-02-24 2005-09-08 Teijin Chem Ltd 廃光ディスクから芳香族ヒドロキシ化合物を得る方法
JP4575046B2 (ja) * 2004-06-25 2010-11-04 帝人化成株式会社 芳香族ジヒドロキシ化合物金属塩水溶液を得る方法
JP4558435B2 (ja) * 2004-10-07 2010-10-06 帝人化成株式会社 芳香族ジヒドロキシ化合物のアルカリ水溶液を得る方法および有機溶媒を回収する方法
JP4606844B2 (ja) * 2004-11-08 2011-01-05 帝人化成株式会社 廃芳香族ポリカーボネートから精製された芳香族ジヒドロキシ化合物のアルカリ金属塩水溶液を得る方法
US7098299B1 (en) 2005-03-16 2006-08-29 United Resource Recovery Corporation Separation of contaminants from polyester materials
CN101166705A (zh) * 2005-04-20 2008-04-23 帝人化成株式会社 由废芳族聚碳酸酯得到芳族二羟基化合物的碱金属盐水溶液的方法
WO2015068628A1 (fr) 2013-11-11 2015-05-14 田岡化学工業株式会社 Procédé permettant de collecter un composé de fluorène de bisphénol à partir d'une résine contenant une structure de fluorène
ES2753375T5 (en) 2014-04-25 2026-03-30 Ineos Styrolution Group Gmbh Polymer blend for metal plating

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DE1234026B (de) * 1961-08-23 1967-02-09 Wolfen Filmfab Veb Verfahren zur Herstellung hochmolekularer Polycarbonate
FR2283766A1 (fr) * 1974-09-04 1976-04-02 Bayer Ag Procede de dissociation de matieres synthetiques, en continu

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US3008980A (en) * 1957-05-29 1961-11-14 Chemische Werke Witten Gmbh Method for utilizing waste polyethylene terephthalate materials
DE1191956B (de) * 1962-08-13 1965-04-29 Bayer Ag Verfahren zum Eindampfen von Loesungen von Kunststoffen in organischen Loesungsmitteln
US3728287A (en) * 1971-10-18 1973-04-17 Eastman Kodak Co Hydrolyzing polyester
US4040991A (en) * 1973-12-10 1977-08-09 Mcdonnell Douglas Corporation Polyurethane foam reconstitution
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Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE910593C (de) * 1941-07-23 1954-05-03 Du Pont Verfahren zur Depolymerisation und Wiedergewinnung von synthetischen linearen Polymeren, insbesondere von Polyamiden
DE1234026B (de) * 1961-08-23 1967-02-09 Wolfen Filmfab Veb Verfahren zur Herstellung hochmolekularer Polycarbonate
FR2283766A1 (fr) * 1974-09-04 1976-04-02 Bayer Ag Procede de dissociation de matieres synthetiques, en continu

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DIE MAKROMOLEKULARE CHEMIE, 65, 1963, Seiten 252-253, "Zersetzung von Polycarbonaten" *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0086358A1 (fr) * 1982-02-06 1983-08-24 Bayer Ag Procédé de préparation de tétraméthylène carbonate et de bis-tétraméthylène dicarbonate
EP0355319A3 (fr) * 1988-07-11 1991-07-31 General Electric Company Procédé de récupération d'un phénol dihydrique à partir de déchets de polyester
EP0641758A3 (fr) * 1993-09-07 1995-05-24 Gen Electric Procédé de récupération de composés bis-hydroxy aromatiques et bis-arylcarbonates au départ de déchets de polycarbonates aromatiques.

Also Published As

Publication number Publication date
EP0000904B1 (fr) 1980-07-23
DE2737693A1 (de) 1979-02-22
DE2860074D1 (en) 1980-11-13
US4212774A (en) 1980-07-15
IT7850772A0 (it) 1978-08-18
IT1106890B (it) 1985-11-18
JPS6051499B2 (ja) 1985-11-14
JPS5448869A (en) 1979-04-17

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