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WO2002038659A2 - Esters d'acide organique dibasique/systeme de cosolvant pour l'affaissement d'un polystyrene alveolaire - Google Patents

Esters d'acide organique dibasique/systeme de cosolvant pour l'affaissement d'un polystyrene alveolaire Download PDF

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Publication number
WO2002038659A2
WO2002038659A2 PCT/US2001/032366 US0132366W WO0238659A2 WO 2002038659 A2 WO2002038659 A2 WO 2002038659A2 US 0132366 W US0132366 W US 0132366W WO 0238659 A2 WO0238659 A2 WO 0238659A2
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WO
WIPO (PCT)
Prior art keywords
cosolvent
weight
solvent
polystyrene
parts
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.)
Ceased
Application number
PCT/US2001/032366
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English (en)
Other versions
WO2002038659A3 (fr
Inventor
Iii Nicholas Edward Kob
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to AU2002213306A priority Critical patent/AU2002213306A1/en
Publication of WO2002038659A2 publication Critical patent/WO2002038659A2/fr
Publication of WO2002038659A3 publication Critical patent/WO2002038659A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C08J11/06—Recovery or working-up of waste materials of polymers without chemical reactions
    • C08J11/08—Recovery or working-up of waste materials of polymers without chemical reactions using selective solvents for polymer components
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • 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
    • C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02—Homopolymers or copolymers of hydrocarbons
    • C08J2325/04—Homopolymers or copolymers of styrene
    • C08J2325/06—Polystyrene
    • 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 an improved solvent system involving a dibasic organic acid ester or mixture of such esters in combination with certain cosolvents in the presence of foamed polystyrene. More specifically but not by way of limitation, the present invention relates to dialkyl adipate, dialkyl glutarate, dialkyl succinate and mixtures thereof in combination with at least one cosolvent selected from the group consisting of ethylene glycol, propylene glycol, propylene carbonate, dimethyl sulfoxide, diacetone alcohol, and isopropyl alcohol.
  • Disposal of polystyrene foam has traditionally been performed by incineration or heat treatment. Incineration, although it is a disposal method, does not recycle the polystyrene material. Reducing the volume of polystyrene by heat treatment causes deterioration of the polystyrene, resulting in inferior recycled material.
  • Another method of recycling polystyrene described in the known art is to dissolve polystyrene into an organic solvent.
  • dimethyl adipate, dimethyl glutarate, dimethyl succinate and mixtures of these diesters have been used commercially in Japan to dissolve foamed polystyrene.
  • Such technology requires that the dissolved polystyrene be recovered from the organic solvent using one of several techniques. Such techniques include but are not limited to precipitation, extrusion, and flash evaporation.
  • the present invention involves an improved solvent system for collapsing and subsequently separating, recovering and/or recycling foamed polystyrene.
  • the novel solvent system of the present invention is felt to not only be useful in prior art processes but also provides an additional property or characteristic of not dissolving the collapsed polystyrene thus physically separating the collapsed softened polystyrene and the liquid solvent system into two different immiscible phases.
  • the solvent system of the present invention does not dissolve the polystyrene. Rather the solvent system in the present invention causes the polystyrene lattice to collapse. The lattice collapse results in the desired reduction in polystyrene volume and simple filtration can separate the collapsed polystyrene from the solvent without precipitation, or flash evaporation.
  • the present invention provides a solvent system comprising for every 100 parts by weight of a dibasic organic acid ester selected from the group consisting of dialkyl adipate, dialkyl glutarate, dialkyl succinate and mixtures thereof, wherein said alkyl groups are either identical or different and have from 1 to 12 carbon atoms, at least one cosolvent selected from the group consisting of;
  • the present invention also provides a solvent/cosolvent polymer mixture comprising from 1 to 40 weight percent polystyrene and from 99 to 60 weight percent of a solvent/cosolvent system comprising a dibasic organic acid ester solvent selected from the group consisting of dialkyl adipate, dialkyl glutarate, dialkyl succinate and mixtures thereof, wherein said alkyl groups are either identical or different and have from 1 to 12 carbon atoms and a cosolvent selected from the group consisting of ethylene glycol, propylene glycol, propylene carbonate, dimethyl sulfoxide, diacetone alcohol, isopropyl alcohol, and mixtures thereof wherein the cosolvent is present in said solvent/cosolvent system from at least 10 weight percent up to 40 weight percent of said solvent/cosolvent system.
  • a solvent/cosolvent system comprising a dibasic organic acid ester solvent selected from the group consisting of dialkyl adipate, dialkyl glutarate, dialkyl succinate and mixtures thereof
  • the liquid phase solvent system useful in the present invention involves a blend or combination of two different miscible components.
  • the first component consists of the dialkyl esters of dibasic organic acids (DBE's), either used individually or as a mixture. Categorically these so- called DBE's are (by themselves) solvents for polystyrene, in that DBE's dissolve polystyrene over a broad range of conditions and concentrations.
  • DBE's dialkyl esters of dibasic organic acids
  • the organic esters useful in the present invention are formed or produced by reacting dibasic organic acids such as adipic acid, glutaric acid, succinic acid, C ⁇ to C 4 alkyl substituted derivatives of these dibasic acids, mixtures thereof and the like with alcohols or mixtures of alcohols having from 1 to 12 carbons.
  • dibasic organic acids such as adipic acid, glutaric acid, succinic acid, C ⁇ to C 4 alkyl substituted derivatives of these dibasic acids, mixtures thereof and the like
  • alcohols or mixtures of alcohols having from 1 to 12 carbons are particularly interested.
  • dimethyl esters of adipic, glutaric, and succinic acid mixtures of these dimetyl esters and esters of 2-ethyl succinic acid and 2-methyl glutaric acid and mixtures of diisobutyl esters of adipic, glutaric, and succinic acids.
  • solvents are commercially available under the product name DBE from E. I. Du Pont
  • the second component of the liquid phase solvent system useful in the present invention consists of an organic liquid cosolvent selected from the group consisting of ethylene glycol, propylene glycol, propylene carbonate, dimethyl sulfoxide, diacetone alcohol, and isopropyl alcohol.
  • these second components are referred to as cosolvents in that they are miscible with the DBE first solvent component over a broad range of conditions and concentrations.
  • these second components are categorically non-solvents for polystyrene.
  • liquid phase solvent system is also referred to herein as a "solvent/cosolvent" with the implicit understanding that by definition what is being referred to is a liquid phase that is capable of collapsing foamed polystyrene into a softened polymeric phase (perhaps better viewed as a plastisized polystyrene) but does not dissolve the polystyrene.
  • the liquid phase solvent system comprises a solvent component capable of dissolving polystyrene and a cosolvent component which does not dissolve polystyrene wherein the amount of cosolvent present in the multi component solvent/cosolvent combination is sufficient to prevent polystyrene from dissolving but insufficient to prevent collapse of the foam polystyrene lattice or cellular foam structure.
  • Each of these parameters describes the bonding characteristic of a solvent in terms of polar, non-polar, and hydrogen bonding tendencies. It is customary to plot solvents on a Hansen map where the x-axis is polar bonding and the y-axis is hydrogen bonding. Such a plot reveals that each solvent has a unique place on the map, which results in different solvency towards polymers. Lists of polymer solubilities in solvents have been developed with emphasis on room temperature and pressure conditions. It is also known that increasing the temperature will increase solvency. What is a non-solvent at a low temperature may become a solvent with increased temperature.
  • Component parameters for polymers may also be assigned and plotted on a Hansen map thus creating a coherent region (or envelope) of solubility on the Hansen map such that any solvent whose parameters reside within this space should dissolve the polymer in question.
  • Hansen Solubility Parameter System a simple mathematical mixing rule can be applied in order to derive or calculate the respective Hansen parameters for a blend of solvents from knowledge of the respective parameters of each component of the blend and the volume fraction of the component in the blend.
  • Figure 1 is a two dimensional Hansen map as described above with the x-axis representing the polar bonding, P ,and the y-axis representing the hydrogen bonding, H - I should be appreciated that this Figure 1 is an approximation in that the third parameter is not being illustrated.
  • the cosolvents ethylene glycol, propylene carbonate (PC), and dimethyl sulfoxide (DMSO) are outside the polystyrene solubility envelope while DBE is within the polystyrene solubility envelope.
  • a tie line drawn between the position of DBE and the position of a cosolvent would intersect the polystyrene solubility envelope such as to quantitatively divide this tie line into two line segments the lengths of which would be proportional to the volume fractions of the solvent and cosolvent necessary to make a blend that would represent the transition from solvent to non-solvent (as predicted by the above mixing rule equations).
  • a tie line drawn between the position of DBE and the position of a cosolvent would intersect the polystyrene solubility envelope such as to quantitatively divide this tie line into two line segments the lengths of which would be proportional to the volume fractions of the solvent and cosolvent necessary to make a blend that would represent the transition from solvent to non-solvent (as predicted by the above mixing rule equations).
  • Hansen parameter mixing rule it has now been discovered that there is an alternate behavior manifested relative to foamed polystyrene for combinations of DBE solvent and selected cosolvents that does not conform to the previously known Hansen parameter mixing rule.
  • the novel compositions of the instant invention exhibit a lack of solubility for polystyrene yet the mixing rule may or may not predict (and frequently does predict) that the blend should dissolve polystyrene.
  • the solvent/cosolvent systems of the present invention exhibit the ability to collapse the foamed polystyrene lattice and/or cellular structure.
  • the relative amount of cosolvent and DBE solvent employed in the liquid phase solvent system will vary predominantly according to the selection of cosolvent and to a lesser degree according to the selection of DBE or DBE mixture.
  • the lower limit of the amount of cosolvent employed relative to DBE will correspond to the onset of insolubility of polystyrene in the blend.
  • the upper limit of amount of cosolvent employed relative to the amount of solvent/cosolvent blend will correspond to the onset of the lack of the ability of the blend to collapse the foamed polystyrene. In other words, there must be sufficient solvent present to collapse the foam structure but not enough cosolvent to inhibit this process. Typically weight percentages of cosolvent numerically in excess 40 % of the blend will lead to rates of collapse of foamed polystyrene that are impractical.
  • the weight percent of cosolvent necessary to achieve the desired results varies from cosolvent to cosolvent with ethylene glycol requiring from 10 to 40 weight % of the liquid phase system; propylene glycol requiring from 10 to 40 weight %, propylene carbonate requiring from 15 to 30 weight %, dimethyl sulfoxide requiring from 35 to 40 weight %, diacetone alcohol requiring from 35 to 40 weight %, and isopropyl alcohol requiring from 30 to 40 weight %.
  • weight percent ranges correspond to from 10 to 66.7 parts by weight ethylene glycol; from 10 to 66.7 parts by weight propylene glycol; from 17.6 to 42.8 parts by weight propylene carbonate; from 53.8 to 66.7 parts by weight dimethyl sulfoxide; from 53.8 to 66.7 parts by weight diacetone alcohol; and from 42.8 to 66.7 parts by weight isopropyl alcohol.
  • the actual forming or making of the liquid solvent phase can be by any of the well-known methods generally practiced in the art. It should be appreciated that the choice of concentration of each cosolvent will be influenced by the above details associated with individual cosolvents. Preferably the amount of the cosolvent employed is in the mid portion of the range unless the ultimate use inherently leads to selective consumption of the solvent or cosolvent thus influencing the preference towards one or other limit of operability. It should also be appreciated that the liquid phase does not have to be free of water and that some water will be present in commercial grades of solvents. For purposes of this invention the presence of some water can in fact be considered an equivalent to a cosolvent and utilized as a supplemental cosolvent.
  • novel solvent systems according to the present invention are viewed as being particularly useful in the presence of polystyrene and preferably used to collapse polystyrene foam and subsequently separate, recover and recycle the collapsed polystyrene.
  • the solvent systems are viewed as being effective in collapsing generally any low density polystyrene foam including in particular both open and closed cellular foams as well the so-called beaded polystyrene foams. Because of the fact that the softened or plastisized polystyrene produced from the collapsed foam floats on the liquid phase, the composition of the instant invention are amenable to simple phase separation, isolation and recovery.
  • Such processes are effective at compositional ranges as low as from 1 weight percent foamed polystyrene and 99 weight percent of a solvent/cosolvent system up to 40 weight percent foamed polystyrene and 60 weight percent of a solvent/cosolvent system.
  • the recovered softened polystyrene is also amenable to reprocessing and removal and recovery of residual solvent by such subsequent processes as injection and/ or extrusion molding.
  • the volatilized solvents withdrawn from such subsequent processing can be advantageously recycled to the foamed polystyrene contact step.
  • Example 1 A series of individual mixtures involving 20 wt. % foamed polystyrene in contact with 80 wt % liquid phase solvent/cosolvent were prepared and observed at room temperature and pressure by adding the foamed polystyrene to the solvent/cosolvent.
  • the DBE solvent employed was a blend of dimethyl esters of succinate, glutarate, and adipate (i.e., 20 wt. % succinate, 60 wt. % glutarate, and 20 wt. % adipate).
  • the relative amount of the cosolvent to DBE i.e., relative weight percentages in the liquid phase was varied such as to establish the concentration range for operability. The following results were obtained:
  • Example 3 Foamed polystyrene was added to a mixture of 80 wt% dimetyl esters (which was 20% succinate, 60% glutarate, 20% adipate) and 20 wt% propylene glycol solvent to determine the capacity of the solvent for collapsing foamed polystyrene. It was found that from 1 wt% to 40 wt.% foamed polystyrene could be added to the solvent/cosolvent.
  • Example 4 Foamed polystyrene was added to 3 separate solvent systems: 80 wt% dimethyl succinate/20 wt% propylene glycol 80 wt% dimethyl glutarate/20 wt% propylene glycol 80 wt% dimethyl adipate/20 wt% propylene glycol
  • the foamed polystyrene was collapsed when placed in all three of the solvent systems.
  • the recovery of the polystyrene was 100% in all three solvent systems.

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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)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

L'invention porte sur un système de solvant amélioré utile pour affaisser un polystyrène alvéolaire et comprenant pour 100 parties en poids d'un ester d'acide organique dibasique sélectionné dans le groupe comprenant un adipate de dialkyle, un glutarate de dialkyle, un succinate de dialkyle et des mélanges de ceux-ci. Ces groupes alkyle sont identiques ou différents et possèdent de 1 à 12 atomes de carbone, au moins un cosolvant sélectionné dans le groupe comprenant (i) de 10 à 66,7 parties en poids d'éthylène glycol, (ii) de 10 à 66,7 parties en poids de propylène glycol, (iii) de 17,6 à 42,8 parties en poids de carbonate de propylène, (iv) de 53,8 à 66,7 parties en poids de diméthylsulfoxyde, (v) de 53,8 à 66,7 parties en poids de diacétone-alcool, et (vi) de 42,8 à 66,7 parties en poids d'isopropanol. Ce système de solvant est notamment utile pour le recyclage et la récupération du polystyrène.
PCT/US2001/032366 2000-11-08 2001-10-18 Esters d'acide organique dibasique/systeme de cosolvant pour l'affaissement d'un polystyrene alveolaire Ceased WO2002038659A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002213306A AU2002213306A1 (en) 2000-11-08 2001-10-18 Solvent system for collapsing foamed polystyrene

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70831300A 2000-11-08 2000-11-08
US09/708,313 2000-11-08

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WO2002038659A2 true WO2002038659A2 (fr) 2002-05-16
WO2002038659A3 WO2002038659A3 (fr) 2002-07-11

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082987A1 (fr) * 2004-02-26 2005-09-09 Oda Industry Co., Ltd. Agent antimousse et de retraction pour le polystyrene expanse et procede de demoussage et de retraction du polystyrene expanse
WO2007009559A1 (fr) * 2005-07-22 2007-01-25 Polimeri Europa S.P.A. Procede de recyclage de polystyrene expanse

Family Cites Families (9)

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Publication number Priority date Publication date Assignee Title
US5486305A (en) * 1994-09-19 1996-01-23 Chesebrough-Pond's Usa Co. Nail polish remover
JPH08218010A (ja) * 1995-02-13 1996-08-27 Neos Co Ltd 水溶性塗料剥離剤
US5629352A (en) * 1995-04-24 1997-05-13 Matsushita Electric Industrial Co., Ltd. Solvent for polystyrene, method for reducing volume of polystyrene foam and method for recycling polystyrene foam
US5712237A (en) * 1995-11-27 1998-01-27 Stevens; Edwin B. Composition for cleaning textiles
JPH09157435A (ja) * 1995-12-06 1997-06-17 Bosai Soken:Kk 発泡スチロール廃材の減容処理方法、回収スチロール樹脂の製造方法および発泡スチロール廃材の減容処理剤
JPH10316797A (ja) * 1997-05-09 1998-12-02 Internatl Foam Solutions Inc 輸送が容易な発泡ポリスチレン減容剤
US5929005A (en) * 1998-12-04 1999-07-27 Decora, Incorporated Graffiti remover which comprises an active solvent, a secondary solvent, an emollient and a particulate filler and method for its use
JP3281336B2 (ja) * 1999-04-19 2002-05-13 株式会社スタイロジャパン 発泡スチロールの脱泡収縮剤及び脱泡収縮方法
JP2001106824A (ja) * 1999-10-04 2001-04-17 Mitsugi Isome 発泡ポリスチレン処理剤およびその製造方法ならびに発泡ポリスチレン回収方法および回収装置

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082987A1 (fr) * 2004-02-26 2005-09-09 Oda Industry Co., Ltd. Agent antimousse et de retraction pour le polystyrene expanse et procede de demoussage et de retraction du polystyrene expanse
WO2007009559A1 (fr) * 2005-07-22 2007-01-25 Polimeri Europa S.P.A. Procede de recyclage de polystyrene expanse
EA012974B1 (ru) * 2005-07-22 2010-02-26 Полимери Эуропа С.П.А. Способ переработки вспененного полистирола
US7728047B2 (en) 2005-07-22 2010-06-01 Polimeri Europa S.P.A. Process for the recycling of expanded polystyrene

Also Published As

Publication number Publication date
WO2002038659A3 (fr) 2002-07-11
AU2002213306A1 (en) 2002-05-21

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