WO2000039205A1 - Extraction d'un materiau recyclable d'une combinaison physique le contenant ainsi que du poly (alkylene carbonate) normalement solide - Google Patents

Extraction d'un materiau recyclable d'une combinaison physique le contenant ainsi que du poly (alkylene carbonate) normalement solide Download PDF

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Publication number
WO2000039205A1
WO2000039205A1 PCT/US1999/031132 US9931132W WO0039205A1 WO 2000039205 A1 WO2000039205 A1 WO 2000039205A1 US 9931132 W US9931132 W US 9931132W WO 0039205 A1 WO0039205 A1 WO 0039205A1
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WIPO (PCT)
Prior art keywords
poly
thε
alkylene carbonate
matεrial
normally
Prior art date
Application number
PCT/US1999/031132
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English (en)
Inventor
Alexander F. Giacco
Joseph G. Sant'angelo
Xiaomao Chen
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Pac Polymers 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.)
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Publication date
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Publication of WO2000039205A1 publication Critical patent/WO2000039205A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/141—Feedstock
    • Y02P20/143—Feedstock the feedstock being recycled material, e.g. plastics
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the invention resides in the chemical arts. More particularly, it relates to the reclamation of recyclable material from a physical combination of such material and plastic material.
  • the plastic material involved in this invention is poly(alkylene carbonate) material.
  • This is material selected from the group consisting of homopoly ers, and random and block copolymers, of alkylene carbonates .
  • Examples of the members of the group are given in such U.S. Patents as 3,585,168 of Inou ⁇ et al., (normally solid homopolymers), 4,763,715 of Cannarsa et al . , (normally solid random copolymers), and 4,665,136 of Santangelo et al., (normally solid block coploymers) .
  • the disclosures of these patents are incorporated by reference.
  • These homopolymers and copolymers are generically referred herein as poly(alkylene carbonates) .
  • Poly(alkylene carbonates) are thermoplastic polymers that can be made by a process in which a mixture of carbon dioxide and one or more than one alkylene oxide is reacted with a catalyst such as a zinc dicarboxylate to form a reaction mixture containing a homopolymer (in the case of one alkylene oxide) or a random copolymer (in the case of more than one alkylene oxide).
  • a catalyst such as a zinc dicarboxylate
  • a mixture of the above reaction mixture, carbon dioxide and another alkylene oxide, or more than one alkylene oxide, are reacted with or without added catalyst to form another reaction mixture, but one containing a block copolymer product.
  • One or more than one such additional reaction steps can be performed as desired.
  • the polymerization reaction conditions, and polymer recovery and work-up steps are disclosed in the above cited patents.
  • the homo- and copolymers obtained by the above process are amorphous and normally solid in that when in the form of shaped articles the articles maintain their shapes under gravity at temperatures up to at least 120°C.
  • the alkylene moiety of the monomeric units of these polymers has two-eight carbons. Larger numbers of carbons, however, are within the broader scope of the invention.
  • poly(alkylene carbonates) include poly(ethylene carbonate), a typical melt flow rate (ASTM 1238, g/lOmin @150°C/2.160kg) of which is 1.4, and the thermal decomposition temperature (TGA) of which is 220°C, and poly(propylene carbonate) , a typical melt flow rate (ASTM 1238, g/lOmin @150°C/2.160kg) of which is 0.9, and the thermal decomposition temperature (TGA) of which is 250°C.
  • poly(ethylene carbonate) a typical melt flow rate (ASTM 1238, g/lOmin @150°C/2.160kg) of which is 1.4, and the thermal decomposition temperature (TGA) of which is 220°C
  • poly(propylene carbonate) a typical melt flow rate (ASTM 1238, g/lOmin @150°C/2.160kg) of which is 0.9, and the thermal decomposition temperature (TGA) of which is 250°C.
  • the U.S. Patent 4,142,021 of Dixon et al . discloses oxygen barrier laminated sheets, useful for packaging food, and comprising a base layer and an adhesive barrier layer bonded to the base layer.
  • the adhesive barrier layer is a poly(alkylene carbonate) which is normally solid at 70°F (21°C).
  • the base layer is polymeric, metallic or fibrous.
  • Examples of a polymeric base layer disclosed in the patent include films of such polymers as ionomers; poly(vinyl chloride); polyethylene; polypropylene; ethylene-propylene copolymers; polystyrene; and polya ides such as polycaprolactam, polyhexamethyl ⁇ ne adipamid ⁇ , copolymer of adipamide and hexamethylene sebacamide, and copolymer of adipamid ⁇ and caprolactam; polyester; aromatic polycarbonates; and the lik ⁇ .
  • Di ⁇ clos ⁇ d as examples of a fibrous base layer are paper substrates such as uncoated wrapping paper.
  • the paper discloses an optional top layer, examples of materials of components of which include not only some of th ⁇ abov ⁇ polymers, but also poly(vinylidine chloride), poly(vinyl alcohol), polysulfone and phenylen ⁇ oxide polymers. While not mentioned in the patent, it is inevitable that the commercial manufactur ⁇ of such laminat ⁇ s and of articles from them will result in scrap. Of course, when the laminates and articles thereof have serv ⁇ d their purpose, they becom ⁇ wast ⁇ .
  • the sintering step is carried out at a temperatur ⁇ at which the poly(alkylene carbonate) binder thermally decomposes to the corresponding alkylene carbonate which vaporizes, or the binder burns (when the step is done in air) to form carbon dioxide and water vapor.
  • a temperatur ⁇ at which the poly(alkylene carbonate) binder thermally decomposes to the corresponding alkylene carbonate which vaporizes, or the binder burns (when the step is done in air) to form carbon dioxide and water vapor.
  • a problem to which this invention provides a solution is th ⁇ recovery or reclamation of recyclable material from the scrap that is inevitabl ⁇ in th ⁇ comm ⁇ rcial manufactur ⁇ of th ⁇ above laminat ⁇ s [which included ⁇ poly(alkylene carbonate) coated paper and th ⁇ like], and of c ⁇ ramic articles by the above described procedure up to the sintering step, and from the waste resulting when such articles and th ⁇ like have served their purpos ⁇ .
  • a probl ⁇ to which this invention provides a solution is the recovery or reclamation of normally solid recyclable material such as , for example, cellulose fiber, polymers, ceramic powders, metal powders, and th ⁇ lik ⁇ , from physical combinations of such with poly(alkyl ⁇ ne carbonates).
  • the invention comprises a process for reclaimimg normally solid r ⁇ cyclable material from a physical combination consisting essentially of such material and normally solid poly(alkylene carbonate) material.
  • the process broadly comprises treating the physical combination to degrade the solid poly(alkylen ⁇ carbonate) material to a liquid without substantially degrading or substantially oxidizing the solid r ⁇ cyclable material, and separating solid recyclable material from the liquid.
  • hydroxy material selected from the group consisting of water and normally liquid, hydroxy aliphatic organic compounds;
  • the physical combination here involved includes (1) a simple mixture of normally solid particles, in fibrous or other form, of recyclable material and of normally solid poly(alkylene carbonate) material; (2) normally solid particles, in fibrous or other form, of recyclable material coated with normally solid poly(alkylene carbonate) material; and (3) normally solid particles, in fibrous or other form, of recyclable mat ⁇ rial in a matrix of normally poly(alkyl ⁇ n ⁇ carbonat ⁇ ) material.
  • the combination in the pref ⁇ rred practice of the process, is reduced to a divided, that is, a particulate, condition. This condition is achieved by conventional ways and means, which include chopping, grinding, and the like.
  • the extent of reduction to a particulate condition can be from coarsly divided to finely divid ⁇ d, but in gen ⁇ ral it is based on practical considerations such as the intend ⁇ d us ⁇ of th ⁇ r ⁇ claimed material, economics of th ⁇ proc ⁇ ss, and th ⁇ lik ⁇ .
  • the divided condition is achieved with a minimum of reduction of the fiber.
  • the process gen ⁇ rally is limit ⁇ d to a physical combination in which th ⁇ th ⁇ rmal decomposition temperature of the recyclable material is substantially above 100°C. If the process is to be carried out without the exclusion of air, the recyclabl ⁇ mat ⁇ rial must be such that the temp ⁇ rature at which relatively rapid, air oxidation begins also must be substantially above 100°C.
  • conc ⁇ pts of this invention include in th ⁇ admixing step catalyst material at a catalytically effectiv ⁇ conc ⁇ ntration, that caus ⁇ s substantial r ⁇ duction of th ⁇ minimum temperature at which occurs significant degradation of the poly( alkylene carbonate) material, substantial acceleration of the degradation of the poly(alkylene carbonate) material, or both such reduction and accel ⁇ ration.
  • Th ⁇ catalyst mat ⁇ rial comprises one or mor ⁇ than on ⁇ catalyst.
  • the catalyst or catalysts include transterification catalysts and hydrolysis catalysts, such as tributyltin dilaurate and the like.
  • An example of a catalytically effective concentration is 100 parts by weight per million parts by weight of the poly(alkylene carbonate) material in th ⁇ physical combination to b ⁇ treated.
  • hydroxy mat ⁇ rial compri ⁇ s one or more than one of the members of the recited group.
  • Normally liquid, hydroxy aliphatic compounds are hydroxy aliphatic compounds that at 20-25°C are liquid under atmosph ⁇ ric pr ⁇ ssure.
  • Pref ⁇ rr ⁇ d normally liquid, hydroxy aliphatic compounds ar ⁇ mono- and polyhydric alcohols.
  • alkanols having one-six carbons examples of which are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl and tert-butyl alcohols, the pentyl alcohols, th ⁇ alicyclic alcohols including cyclohexanol and the like, and such polyhydric aliphatic alcohols as glycerol and the lik ⁇ .
  • Th ⁇ quantity of hydroxy mat ⁇ rial ad ix ⁇ d with th ⁇ physical combination should be about 1-30%, preferably 3-10%, by w ⁇ ight of th ⁇ physical combination to b ⁇ tr ⁇ ated.
  • t ⁇ mp ⁇ ratur ⁇ rang ⁇ in which th ⁇ mixtur ⁇ of th ⁇ physical combination and the hydroxy mat ⁇ rial is treated is as set forth above.
  • the r ⁇ cyclabl ⁇ mat ⁇ rial consists ⁇ ssentially of cellulose fiber
  • the hydroxy material comprises water
  • no catalyst material is added or otherwise part of the initial mixture
  • oxygen is not excluded in the practice of the process steps
  • a pref ⁇ rr ⁇ d tr ⁇ atm ⁇ nt t ⁇ mp ⁇ rature range is 120-200°C
  • a mor ⁇ pr ⁇ f ⁇ rred rang ⁇ is 150-180°C.
  • At th ⁇ s ⁇ t ⁇ p ⁇ ratur ⁇ th ⁇ r ⁇ is a good balance between the rate of oxidation of the cellulose, which should be as low as practicable, and the rate at which the poly( alkylene carbonate) material becomes liquid, which should b ⁇ as high as practicable.
  • Separation of the recyclable material from the reaction mixture i ⁇ done aft ⁇ r substantially all of th ⁇ poly(alkyl ⁇ ne carbonate) material has become material that is liquid in the separation temperatur ⁇ range.
  • the separation i ⁇ carried out while the temperatur ⁇ of the reaction mixture i ⁇ still high enough to maintain in th ⁇ liquid state th ⁇ alkylene carbonate( s) , low ⁇ r molecular weight poly( alkylene carbonate) material, or both, formed in th ⁇ treatment step.
  • Such t ⁇ mperature generally is in rang ⁇ from about 30 to about 100°C.
  • S ⁇ paration is don ⁇ by conv ⁇ ntional ways and means, for exampl ⁇ , distillation, filtration, and th ⁇ lik ⁇ .
  • a feature of advantage of the process of this invention is that useful products of degradation of th ⁇ ⁇ tarting poly( alkylene carbonate) material al ⁇ o can be obtained.
  • Separation of the crystallized alkylene carbonate material and the liquid hydroxy material is carried out by conventional ways and means for separating ⁇ olid ⁇ and liquid ⁇ , which include filtration, evaporation by the application of heat, vacuum, or both, and the like.
  • Alkyl ⁇ n ⁇ carbonat ⁇ s ar ⁇ useful as plasticizers for poly( alkylene carbonates), and as monomers for th ⁇ production of poly( alkyl ⁇ n ⁇ carbonates).
  • the poly(alkylene carbonate) material i ⁇ degraded to lower molecular weight poly(alkylene carbonate) material.
  • the polymer chains in such mat ⁇ rial ar ⁇ hydroxy t ⁇ r inated.
  • the monomeric units of th ⁇ polymers that make up the lower molecular weight material corr ⁇ spond to th ⁇ monom ⁇ ric units of th ⁇ poly ⁇ rs that mak ⁇ up the poly( alkylene carbonate) material befor ⁇ b ⁇ ing tr ⁇ ated according to th ⁇ treatm ⁇ nt ⁇ t ⁇ p. How ⁇ ver, there are not as many such units in the polymer chains of the degraded polymer mat ⁇ rial.
  • th ⁇ tr ⁇ atm ⁇ nt ⁇ tep is carried out to the ⁇ xt ⁇ nt the poly( alkylene carbonate) material becom ⁇ liquid at l ⁇ a ⁇ t in th ⁇ separation temperature range. If the treatm ⁇ nt st ⁇ p is carri ⁇ d out just to the point the mat ⁇ rial becomes liquid, the resulting degraded polymer material gen ⁇ rally is solid at 20-25°C. On th ⁇ oth ⁇ r hand, the treatment step can be continued to where the degraded polymer material even at 20-25°C is a viscous liquid.
  • the degrad ⁇ d polym ⁇ r raat ⁇ rial when it is cool ⁇ d to 20-25°C, it can be separated from residual hydroxy material. Separation of the degraded polymer material and the liquid hydroxy material i ⁇ carried out by conventional ways and means, which include filtration, decantation, centrifugation, evaporation by the application of heat, vacuum, or both, and the like.
  • the degraded polymer product thus obtained has not only a lower molecular weight poly(alkylen ⁇ carbonat ⁇ ) mat ⁇ rial content, but also an alkylene carbonate material content, the concentration of which is dependent on the length of time the degraded polymer material is subjected to the above elevated temp ⁇ ratur ⁇ and pr ⁇ sur ⁇ condition ⁇ .
  • This alkylene carbonate content can be of advantage as a plasticizer of the lower molecular weight poly(alkylen ⁇ carbonate) mat ⁇ rial if it is normally ⁇ olid, and the product alone or in phy ⁇ ical combination with other material, i ⁇ extruded, inject ⁇ d mold ⁇ d, or th ⁇ lik ⁇ .
  • the alkylen ⁇ carbonate content of the degrad ⁇ d polym ⁇ r product is not want ⁇ d, or its conc ⁇ ntration must be reduced to an acceptable level
  • the alkylene carbonate content in whole or in part is separated from the lower molecular weight poly(alkylene carbonate) material by extraction with a solvent (for example, methanol) for th ⁇ alkylen ⁇ carbonat ⁇ content.
  • a solvent for example, methanol
  • the lower molecular weight poly( alkylen ⁇ carbonate) material thus obtained has utility a ⁇ a sacrificial binder in the manufacture of articles from ceramic, metallic and glass powders in those instance ⁇ wher ⁇ it i ⁇ de ⁇ ired or requir ⁇ d that th ⁇ binder thermally decompose or burn at a temperatur ⁇ substantially lower than th ⁇ thermal decomposition or burning temperature of the higher molecular weight poly(alkylen ⁇ carbonate) material. Because the polymer chains of the lower molecular weight poly(alkylene carbonate) material are hydroxy terminated, ⁇ uch material al ⁇ o ha ⁇ utility as isocyanate r ⁇ active material in the production of polyurethan ⁇ and articles ther ⁇ from.
  • the hydroxyl moieties ther ⁇ of can b ⁇ reacted with an alkenylacyl halide (for ⁇ xampl ⁇ , acryloyl chlorid ⁇ ) or an alkenyl carboxylic acid (for example, methacrylic acid) to form functional groups that, with th ⁇ aid of a conventional chemical initiator, can be cros ⁇ -linked with molecular energizing radiation such a ⁇ light.
  • Th ⁇ ⁇ xtent of poly( alkylene carbonat ⁇ ) material degradation i ⁇ time d ⁇ pendent at any given treatm ⁇ nt t ⁇ mp ⁇ rature.
  • the high ⁇ r th ⁇ mol ⁇ cular wight of a poly( alkylene carbonate) the longer i ⁇ the tim ⁇ to degrade it at a given temperatur ⁇ .
  • Al ⁇ o, th ⁇ high ⁇ r th ⁇ number of carbon atom ⁇ in the alkylen ⁇ carbonat ⁇ mono ⁇ ric units of a poly( alkylene carbonate) the higher the temperatur ⁇ ⁇ hould b ⁇ for its degradation.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention porte sur un procédé d'extraction d'un matériau recyclable normalement solide d'une combinaison physique le contenant ainsi que du poly(alkylène carbonate) et consistant (1) à soumettre un mélange de ladite combinaison et d'un matériau hydroxy normalement liquide à une certaine température et à une certaine pression jusqu'à ce que le poly(alkylène carbonate) se soit dégradé en liquide, et (2) à séparer le matériau recyclable de la partie liquide du mélange résultant. L'invention porte également sur le processus de séparation du poly(alkylène carbonate) de poids moléculaire moindre, de l'alkylène carbonate ou de leur mélange, d'avec le liquide.
PCT/US1999/031132 1998-12-30 1999-12-29 Extraction d'un materiau recyclable d'une combinaison physique le contenant ainsi que du poly (alkylene carbonate) normalement solide WO2000039205A1 (fr)

Applications Claiming Priority (2)

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US11423698P 1998-12-30 1998-12-30
US60/114,236 1998-12-30

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WO2000039205A1 true WO2000039205A1 (fr) 2000-07-06

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019207260A1 (fr) 2018-04-27 2019-10-31 Arkema France Procede de recyclage de thermoplastique par depolymerisation courte

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4051212A (en) * 1974-09-04 1977-09-27 Bayer Aktiengesellschaft Process for the continuous degradation of plastics
US4605762A (en) * 1982-04-23 1986-08-12 Celanese Mexicana S.A. Depolymerization of condensation polymers
US4763715A (en) * 1987-12-14 1988-08-16 Arco Chemical Company Process for preparing polycarbonate terpolymer foam suitable for lost foam casting
US5391802A (en) * 1992-06-22 1995-02-21 Bayer Aktiengesellschaft Process for cleaving polycarbonates into bisphenols and diaryl carbonates

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4051212A (en) * 1974-09-04 1977-09-27 Bayer Aktiengesellschaft Process for the continuous degradation of plastics
US4605762A (en) * 1982-04-23 1986-08-12 Celanese Mexicana S.A. Depolymerization of condensation polymers
US4763715A (en) * 1987-12-14 1988-08-16 Arco Chemical Company Process for preparing polycarbonate terpolymer foam suitable for lost foam casting
US5391802A (en) * 1992-06-22 1995-02-21 Bayer Aktiengesellschaft Process for cleaving polycarbonates into bisphenols and diaryl carbonates

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019207260A1 (fr) 2018-04-27 2019-10-31 Arkema France Procede de recyclage de thermoplastique par depolymerisation courte
FR3080622A1 (fr) * 2018-04-27 2019-11-01 Arkema France Procede de recyclage de thermoplastique par depolymerisation courte

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