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GB1093884A - Method of recovering polyol and amine derivatives by the decomposition of polyurethane substances - Google Patents

Method of recovering polyol and amine derivatives by the decomposition of polyurethane substances

Info

Publication number
GB1093884A
GB1093884A GB1171165A GB1171165A GB1093884A GB 1093884 A GB1093884 A GB 1093884A GB 1171165 A GB1171165 A GB 1171165A GB 1171165 A GB1171165 A GB 1171165A GB 1093884 A GB1093884 A GB 1093884A
Authority
GB
United Kingdom
Prior art keywords
decomposition
polyurethane
preparation
amine
polyol
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.)
Expired
Application number
GB1171165A
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.)
Bridgestone Corp
Original Assignee
Bridgestone Corp
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 Bridgestone Corp filed Critical Bridgestone Corp
Publication of GB1093884A publication Critical patent/GB1093884A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00Recovery or working-up of waste materials
    • C08J11/04Recovery or working-up of waste materials of polymers
    • C08J11/10Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/28Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic compounds containing nitrogen, sulfur or phosphorus
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02WCLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00Technologies for solid waste management
    • Y02W30/50Reuse, recycling or recovery technologies
    • Y02W30/62Plastics recycling; Rubber recycling

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)

Abstract

Polyurethane foams and elastomers are thermally decomposed, in the presence of an amine, to yield a polyol, which is the polyether or polyester from which the polyurethane was formed, and the amine derivative of the polyisocyanate. The amine also serves as solvent. Suitable amines include aliphatic e.g. di-n-butylamine, ethylenediamine, and triethanolamine, cycloaliphatic e.g. cyclohexylamine, piperazine and piperidine, aromatic e.g. aniline, benzylamine, the toluidines, anisidines and p-phetidine, o-phenylenediamine, and a -naphthylamine and heterocyclic e.g. pyridine, a - and b -picolines, N - methyl and N - ethyl morpholine, and pyrazole. After the decomposition, one or more layers appear, and each layer is distilled under reduced pressure, the polyol being obtained as the residue. The amine derivative is isolated by recrystallization of the distillate. In the examples, the preparation and decomposition of polyurethane foams is described together with tests to establish the identical nature of the products of decomposition and the reactants of preparation. A mixture of 2,4- and 2,6-tolylene diisocyanate is used for the preparation of the polyurethane in examples (1-8) and 2,4 and 2,6-diaminotoluene are obtained from the ensuing decomposition. Similarly 1,5-naphthylenediamine in Example (9) and 4,41-diamino diphenyl methane in Example (10) are also obtained from the decomposition. The polyols recovered by the above methods are reconverted to polyurethanes. The reformed polyurethanes are cured using 4,41-methylene bis (2-chloroaniline) in Example (8) and butanediol in Example (9). The polyols used are: (1) the product of polymerization of propylene oxide with glycerol; (3) the product of polymerization of propylene oxide with sorbitol; (4) a polyester obtained from adipic acid and diethylene glycol; (8) polytetramethylene ether glycol; and (9) a polyester obtained from adipic acid and ethylene glycol.ALSO:Polyurethane foams and elastomers are thermally decomposed, in the presence of an amine to yield a polyol, which is the polyether or polyester from which the polyurethane was formed, and the amine derivative of the polyisocyanate. The amine also serves as solvent. Suitable amines include aliphatic, e.g. di-n-butylamine, ethylenediamine and triethanolamine, cycloaliphatic, e.g. cyclohexylamine, piperazine and piperidine, aromatic, e.g. aniline, benzylamine, the toluidines, anisidines, and p-phenetidine, o-phenylene-diamine, and a -naphthylamine, and heterocyclic, e.g. pyridine a - and b -picolines, N-methyl and N-ethyl morpholine, and pyrazole. After the decomposition, one or more layers appear, and each layer is distilled under reduced pressure, the polyol being obtained as the residue. The amine derivative is isolated by recrystallization of the distillate. In the examples, the preparation and decomposition of polyurethane foams is described together with tests to establish the identical nature of the products of decomposition and the reactants of the preparation. A mixture of 2,4- and 2,6-tolylenediisocyanates is used for the preparation of the polyurethane in Examples (1-8) and 2,4- and 2,6-diamino toluene are obtained from the ensuing decomposition. Similarly, 1,5-naphthylene-diamine in Example (9) and 4,41-diamino diphenylamine in Example (10) are also obtained from the decomposition. The polyols used are:-(1) the product of polymerization of propylene oxide with glycerol, (3) the product of polymerization of propylene oxide with sorbitol, (4) a polyester obtained from adipic acid and diethylene glycol, (8) polytetramethylene ether glycol, and (9) a polyester obtained from adipic acid and ethylene glycol.
GB1171165A 1964-03-30 1965-03-19 Method of recovering polyol and amine derivatives by the decomposition of polyurethane substances Expired GB1093884A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1737064 1964-03-30
JP6766664 1964-12-03

Publications (1)

Publication Number Publication Date
GB1093884A true GB1093884A (en) 1967-12-06

Family

ID=26353878

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1171165A Expired GB1093884A (en) 1964-03-30 1965-03-19 Method of recovering polyol and amine derivatives by the decomposition of polyurethane substances

Country Status (3)

Country Link
BE (1) BE673069A (en)
DE (1) DE1570249B2 (en)
GB (1) GB1093884A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2442387A1 (en) * 1974-09-04 1976-03-18 Bayer Ag PROCESS FOR CONTINUOUS DEGRADATION OF PLASTICS
EP0507426A1 (en) * 1991-04-01 1992-10-07 Texaco Chemical Company Process for dissolving polyurethane foams or removing them from substrates
US6515036B2 (en) 2000-04-04 2003-02-04 Mitsui Takeda Chemicals Inc. Method of decomposing a polyurethane
WO2024187296A1 (en) * 2023-03-10 2024-09-19 上纬创新育成股份有限公司 Degradation method for polyurethane foam

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2442387A1 (en) * 1974-09-04 1976-03-18 Bayer Ag PROCESS FOR CONTINUOUS DEGRADATION OF PLASTICS
EP0507426A1 (en) * 1991-04-01 1992-10-07 Texaco Chemical Company Process for dissolving polyurethane foams or removing them from substrates
US5183514A (en) * 1991-04-01 1993-02-02 Texaco Chemical Company Process for dissolving or removing rigid polyurethane foam by contacting with 1,2-dimethyl imidazole
US6515036B2 (en) 2000-04-04 2003-02-04 Mitsui Takeda Chemicals Inc. Method of decomposing a polyurethane
WO2024187296A1 (en) * 2023-03-10 2024-09-19 上纬创新育成股份有限公司 Degradation method for polyurethane foam

Also Published As

Publication number Publication date
DE1570249B2 (en) 1972-01-05
DE1570249A1 (en) 1970-03-12
BE673069A (en) 1966-03-16

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