US20020037939A1 - Solvent-based recovery and recycle of polyamide material - Google Patents

Solvent-based recovery and recycle of polyamide material Download PDF

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Publication number
US20020037939A1
US20020037939A1 US09/876,244 US87624401A US2002037939A1 US 20020037939 A1 US20020037939 A1 US 20020037939A1 US 87624401 A US87624401 A US 87624401A US 2002037939 A1 US2002037939 A1 US 2002037939A1
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polyamide
solvent
depolymerized
solution
post
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Michael McKinnon
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Priority to US10/808,854 priority patent/US7319113B2/en
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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
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery 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
    • C08J11/22—Recovery 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 oxygen-containing compounds
    • C08J11/24—Recovery 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 oxygen-containing compounds containing hydroxyl 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/04—Preparatory processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/02—Separating plastics from other materials
    • B29B2017/0213—Specific separating techniques
    • B29B2017/0293—Dissolving the materials in gases or liquids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2077/00—Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
    • 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
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such 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
    • 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

  • This invention relates to a solvent-based process for the recovery and recycle of polyamide material from post-industrial and post-consumer products.
  • this invention allows the separation of very small solid particles, such as TiO 2 , from the polyamide material to be recycled.
  • Aliphatic polyamides particularly nylon 6 and nylon 66
  • carpets and automobile air bags contain large portions of polymers with a high polyamide content.
  • these nylon products are ideal for recovery and recycle.
  • concerns over efficient resource utilization and environmental protection have created a need for the recovery and recycle of nylon from discarded post-industrial and post-consumer products.
  • Recycle processes are already used to recycle polyamide carpet waste in order to minimize the portion of the polyamide-containing carpet waste that has to be discarded.
  • Mechanical means such as grinding and crushing, are known means for separation of solid polyamide material from foreign materials such as carpet backing, etc. Mechanical separation yields a low grade recycled product with limited uses.
  • the process In order to produce a high-quality recycled polyamide product, the process must remove impurities such as dyes, cotton thread, delusterants (TiO 2 ), dirt, and oil, among other things, that cannot be removed by mechanical means alone.
  • polyols and carboxylic acids have many attributes of ideal solvents for polyamide recycle and recovery.
  • polyols and carboxylic acids have not been attractive solvents because they are reactive with polyamides, and thereby have contributed to the degradation of molecular weight of the polyamide.
  • slight losses in molecular weight have been tolerated, however, it has been thought that more significant degradation is to be avoided because recovered degraded polyamides are unsuitable for either extrusion purposes (e.g. fibers and films) or use as molding compounds.
  • U.S. Pat. No. 5430068 to Subramanian discloses a process to recover polyamides using anhydrous polyols or aliphatic carboxylic acids having from 2 to 6 carbon atoms as the solvent.
  • the process also includes the step of rapidly quenching the polyamide solution with an additional quantity of solvent to avoid any significant degradation of the polyamide.
  • glycols as solvents, such as acetic acid and water, ethylene glycol and propylene glycol.
  • Glycol-based solvent processes take advantage of the different solvencies of nylon 6 and nylon 66 at particular temperatures to separate one from the other.
  • glycols also react with the polyamides, in this case to create higher molecular weight polyamides.
  • the residence time i.e. the time that the polyamide is contacted with the solvent must be short to avoid glycol reaction with the polyamide.
  • Aliphatic alcohols have been suggested for use as solvents in processes to recycle and recover polyamides.
  • Methanol in particular, has been shown to be useful in the separation of nylon 6 from nylon 66 .
  • aliphatic alcohol solvents are effective under mild conditions, i.e. low temperature and short residence time.
  • U.S. Pat. No. 5840773 to Booij et al discloses a process to recover polyamides from carpet waste using an aliphatic alcohol as the solvent. The process conditions are such that “virtually no polyamide is decomposed” so that directly reusable polyamides are obtained from the process.
  • U.S. Pat. No. 6036726 to Yang et al also discloses a solvent-based process to recover polyamides. Under the conditions described, the molecular weight of the recovered polyamide is “substantially unchanged”, making the polyamide readily available for re-use.
  • This problem is addressed by the present invention in which a solvent-based process is provided to recover polyamides from post-industrial and post-consumer products.
  • the process of the present invention allows for the separation of TiO 2 and other fine insoluble particles by partially depolymerizing the polyamide to decrease its viscosity.
  • the process further comprises the step of repolymerizing the depolymerized polyamide.
  • FIG. 1 is a flow chart illustrating the steps in the preferred embodiment of the process of the present invention.
  • Step 5 is a preferred step:
  • Step 1 Contacting the polyamide-containing post-industrial and post-consumer product with a suitable solvent.
  • Step 2 Dissolving and partial depolymerizing the polyamide in the solvent at a predetermined temperature and pressure for a time sufficient to decrease the average molecular weight of the polyamide to less that 90% of its original average molecular weight.
  • Step 3 Filtering the solution to remove solid impurities.
  • Step 4 Recovering the depolymerized polyamide from the solution.
  • Step 5 Repolymerizing the depolymerized polyamide so that it can be used to make other useful products.
  • Step 1 nylon-containing post-industrial and post-consumer products are collected.
  • nylon 6 The majority of recyclable nylon consists of nylon 6 and nylon 66 formed by the homopolymerization of 6 -aminocaproic acid, also known as e-caprolactam.
  • Nylon 66 also known as nylon 6 , 6 , is the polyamide formed by the reaction of adipic acid with hexamethylenediamine. It will be understood, however, that the process of the present invention is not limited to nylon 6 and nylon 66 , but also includes other polyamides such as nylon 610 and nylon 612 .
  • Waste and scrap nylon 6 and nylon 66 are available from many sources including but not limited to rejects, turnings and trimmings from manufacturing processes, automotive parts, carpets, clothing, etc.
  • the waste post-industrial and post-consumer products may be prepared for recycling by any method that produces particulate material such as grinding, crushing, etc. Alternately, if the source material is small enough, it may be used whole.
  • Nylon fiber may be used as is or may also be ground into smaller pieces. Nylon fiber in carpets may be separated from the carpet backing, i.e. by shearing.
  • the nylon-containing products are then contacted with a suitable solvent capable of dissolving and depolymerizing nylon under predetermined conditions.
  • the solvent used may be an aliphatic alcohol, such as ethanol or methanol.
  • methanol is used.
  • the alcohol is preferably used in an anhydrous form, but it may also be in a solution of at least 90% by weight alcohol. Additionally, mixtures of ethanol, methanol or water may be used as the solvent, so long as the water content is no more than 10% by weight.
  • Step 2 the polyamide is dissolved and partially depolymerized in the solvent in a reactor capable of operating at elevated temperatures and pressures.
  • the temperature of the reactor is elevated and pressure is increased to maintain a liquid phase. Sufficient residence time is needed to allow sufficient depolymerization of the polyamide to occur.
  • the preferred temperature range is 160 to 210° C.
  • the preferred pressure range is 350 to 600 psig
  • the residence time necessary for depolymerization ranges from about 30 to about 400 minutes. Under these controlled conditions, depolymerization of the polyamide reduces the average molecular weight of the polyamide from between about 10% to about 75%. This results in a decrease in the viscosity of the solution.
  • Step 3 the solution containing the dissolved and depolymerized nylon and insoluble materials is passed through suitable filtration media to remove and separate the insoluble materials from the solution.
  • suitable filtration media Any suitable method of filtration maybe used.
  • the preferred filtration method involves passing the dissolved and depolymerized nylon solution through glass fibers.
  • glass wool filtration involves passing the solution, under pressure of about 500 psig, through glass wool supported by wire mesh. Throughout this filtration step, all operating conditions including temperature, pressure and solvent concentration are maintained within the above-described ranges to keep the dissolved and depolymerized nylon in solution.
  • This filtration step separates insoluble material including sub-micron sized particulate matter such as TiO 2 , from the solution. This results in a substantially more purified, low viscosity solution containing the depolymerized nylon. Because the nylon is not only dissolved but also depolymerized, much finer solid particles can be removed than would otherwise be possible with a solution containing large, intact higher viscosity nylon polymer. Finer filtration makes possible the removal of small sized impurities such as TiO 2 that are commonly found in nylon-containing products. In addition, because the nylon to be recyled is depolymerized, greater concentrations of nylon in solvent and longer residence times in the reactor are possible while still allowing for an acceptable recovered product. This is because the depolymerized nylon has a lower viscosity than that of the original, dissolved polymerized nylon.
  • the depolymerized nylon may be recovered by any recovery method known to persons skilled in the art, such as precipation of the depolymerized polyamides, spray drying, and flash evaporation.
  • the depolymerized nylon is precipitated out and removed from the filtered solution of Step 3 by either cooling the solution or diluting the solvent with an additive that forces the nylon out of solution, such as an anti-solvent agent.
  • the depolymerized nylon is separated from the solvent by filtration or centrifugation. Residual solvent must be removed from the depolymerized nylon before repolymerization.
  • Removing nylon from the solvent in Step 4 produces both a reduced molecular weight (depolymerized) nylon and a solvent with soluble impurities therein.
  • the solvent may be purified by existing technology and recycled back to Step 1 at the beginning of this process.
  • Repolymerization of the recovered polyamide is the final optional step in the process.
  • Repolymerization begins with low-viscosity, low molecular weight polyamide and results in a higher viscosity, higher quality polyamide suitable for end-use processing.
  • the repolymerization of nylon can be done readily by one of two standard methods: solid-phase repolymerization or melt-phase repolymerization. The choice of repolymerization method depends on the need for greater residence time, i.e. the time needed for repolymerization to occur.
  • the solid-phase method of repolymerizing nylon is carried out at any suitable temperature below the melting point of the polyamide.
  • the upper temperature limit is 220° C. whereas for Nylon 66 it is 265° C.
  • the preferred temperature range for solid-phase repolymerization is 160-200° C.
  • Solid-phase repolymerization has no residence time limit, i.e. the repolymerization process may take as long as is needed, and therefore is useful for recovery of significantly depolymerized polyamides. Solid-phase repolymerization yields a high quality, high molecular weight polyamide.
  • the repolymerization occurs at a temperature above the melting temperature of the polyamide; the preferred temperature range of operation is 270-300° C. and the preferred residence time limit for repolymerization is 1-30 minutes.
  • Melt-phase repolymerization is a faster, simpler process compared to solid-phase repolymerization and is useful if the final product to be made from the repolymerized polyamide is an extruded product.
  • the recycled and recovered polyamide can be manufactured into nylon-containing industrial and consumer products.
  • Nylon fibers were mechanically separated from carpet waste to produce a mixture containing 92% Nylon 66. The other 8% was a mixture of latex and polypropylene.
  • 150 g of the separated Nylon fibers was then added to a one gallon stainless steel reactor equipped with an agitator. The reactor had a drain line on the bottom that was equipped with a shut-off valve and a metering valve.
  • a wire mesh screen (80 mesh) and glass filters (Whatman type GF/D and GF/B) were placed on the bottom of the reactor and a metal ring was inserted to hold the filters in position. Approximately 1 ⁇ 2 inch of glass wool was placed on top of the filters.
  • the reactor was sealed and heated to 185° C.
  • Two liters of methanol were pumped at a rate of 110 ml/min through a preheater and into the reactor.
  • the system was then agitated and held at an operating temperature of 185° C. for 30 minutes.
  • the shutoff valve was then opened on the drain line allowing the solution to flow through the filter system.
  • the filtered solution flowed through the metering valve and into a product collection tank filled with an ice/water mixture, causing the nylon to precipitate.
  • the precipitated nylon was separated from the solution with a wire mesh screen and removed to dry in a vacuum oven.
  • the nylon product was analyzed by hydrolysis followed by gas chromatography for nylon content; molecular weight was determined by relative viscosity in 85% formic acid. The results are summarized in Table 1.
  • relative viscosity is defined as the ratio of the viscosity of an 8.4% (by weight) solution of the polymer dissolved in 85% formic acid to the absolute viscosity of the 85% formic acid used. Polyamide from the product was weighed and dissolved in 85% formic acid. The viscosity was determined by automated measurement of the time required for the sample to flow through a calibrated Ubbelohde viscometer (drop time).
  • Methyl group occurrence per 106 gram of polyamide was used as an estimate of the occurrence of reaction between the solvent and the polymer. This shows the extent to which the solvent reacted with the polymer. This was measured by proton nuclear magnetic resonance.
  • Example 2 was run at the same conditions as Example I except that the hold time in the reactor at operating conditions after solvent addition was 60 minutes. The results are summarized in Table I
  • Example 3 was run at the same conditions as Example 1 except that the hold time in the reactor at operating conditions after solvent addition was 120 minutes. The results are summarized in Table 1.
  • Example 4 was run at the same conditions as Example 1 except 100 g of Nylon was initially added to the reactor and the hold time in the reactor after solvent addition was 180 minutes. The results are summarized in Table 1.
  • Example 5 was run at the same conditions as Example 1 except 100 g of Nylon was initially added to the reactor, the operating temperature was 175° C., and the hold time in the reactor after solvent addition was 120 minutes. The results are summarized in Table 1.
  • Example 6 was run at the same conditions as Example 1 except the product collected was placed in an oven that was nitrogen sparged for 170 minutes at 190° C. The results are summarized in Table 1.
  • Example 7 was run at the same conditions as Example 1 mexcept the product collected was placed in an oven that was nitrogen sparged for 340 minutes at 190° C. The results are summarized in Table 1. TABLE 1 Sample Relative Viscosity Methyl (eq/106g) Feedstock 50 0 Example 1 32 53 Example 2 27 72 Example 3 20 85 Example 4 19 111 Example 5 21 111 Example 6 60 24 Example 7 72 34
  • Example 8 was run using conditions similar to Example 1.
  • the reactor system was modified with a second pressurized vessel for product collection. Once the solution was passed through the filters, it was collected in the second vessel and allowed to cool. Cooling was accomplished by flowing water through a cooling coil installed in the vessel. After cooling the precipitated polymer was separated from the solvent. Residual solvent was removed from the precipitated polymer by drying in a vacuum oven.
  • the charge to the reactor was 200 grams and the operating temperature was 170° C.
  • the hold time in the reactor after solvent addition was 30 minutes.
  • the final product was analyzed for titanium dioxide content by neutron activation analysis. The results are summarized in Table 2 below.
  • EXAMPLE 9 was run under conditions identical to Example 8 except that the hold time in the reactor after solvent addition was 60 minutes. The results are also summarized in Table 2.
  • Example 10 was run under conditions identical to Example 8 except that the hold time in the reactor after solvent addition was 90 minutes. The results are also summarized in Table 2. TABLE 2 Sample Ti (neutron analysis) Feedstock 1400 ppm Example 8 210 ppm Example 9 145 ppm Example 10 46 ppm

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  • 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)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Polyamides (AREA)
  • Filtering Materials (AREA)
US09/876,244 2000-06-08 2001-06-07 Solvent-based recovery and recycle of polyamide material Abandoned US20020037939A1 (en)

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US09/876,244 US20020037939A1 (en) 2000-06-08 2001-06-07 Solvent-based recovery and recycle of polyamide material
US10/808,854 US7319113B2 (en) 2000-06-08 2004-03-24 Solvent-based recovery and recycle of polyamide material

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US09/876,244 US20020037939A1 (en) 2000-06-08 2001-06-07 Solvent-based recovery and recycle of polyamide material

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EP (1) EP1294796B1 (de)
JP (1) JP2003535942A (de)
CA (1) CA2409837A1 (de)
DE (1) DE60121948T2 (de)
WO (1) WO2001094457A2 (de)

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EP1294796B1 (de) 2006-08-02
DE60121948D1 (de) 2006-09-14
CA2409837A1 (en) 2001-12-13
WO2001094457A2 (en) 2001-12-13
JP2003535942A (ja) 2003-12-02
US20040186190A1 (en) 2004-09-23
EP1294796A2 (de) 2003-03-26
WO2001094457A3 (en) 2002-05-02
US7319113B2 (en) 2008-01-15

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