WO2005082826A1 - Procedimiento quimico de reciclado de polietilentereftalato (pet) de desecho - Google Patents

Procedimiento quimico de reciclado de polietilentereftalato (pet) de desecho Download PDF

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Publication number
WO2005082826A1
WO2005082826A1 PCT/IB2004/000257 IB2004000257W WO2005082826A1 WO 2005082826 A1 WO2005082826 A1 WO 2005082826A1 IB 2004000257 W IB2004000257 W IB 2004000257W WO 2005082826 A1 WO2005082826 A1 WO 2005082826A1
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WIPO (PCT)
Prior art keywords
terephthalic acid
reaction
ethylene glycol
alcoholic
reaction medium
Prior art date
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Ceased
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PCT/IB2004/000257
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English (en)
Spanish (es)
French (fr)
Inventor
Arturo Guadalupe Fregoso-Infante
Roxanna Vega-Rangel
Maricruz Figueroa-Gomez-Crespo
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Individual
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Individual
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Publication date
Priority to ES04705473T priority Critical patent/ES2328139T3/es
Priority to DE602004022199T priority patent/DE602004022199D1/de
Priority to US10/587,518 priority patent/US7893122B2/en
Priority to PCT/IB2004/000257 priority patent/WO2005082826A1/es
Priority to KR1020067015142A priority patent/KR100983349B1/ko
Priority to AU2004316446A priority patent/AU2004316446B2/en
Priority to JP2006550315A priority patent/JP4647625B2/ja
Priority to PT04705473T priority patent/PT1710226E/pt
Application filed by Individual filed Critical Individual
Priority to EP04705473A priority patent/EP1710226B1/en
Priority to CA2595393A priority patent/CA2595393C/en
Priority to DK04705473T priority patent/DK1710226T3/da
Publication of WO2005082826A1 publication Critical patent/WO2005082826A1/es
Priority to IL176986A priority patent/IL176986A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/26—1,4 - Benzenedicarboxylic acid
    • 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
    • C08J11/16—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 inorganic 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
    • 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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials
    • 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 present invention is related to the techniques used in the Chemical Industry for the recovery of chemical products from waste polymeric materials, and more particularly, it is related to a chemical recycling process of waste polyethylene terephthalate (PET).
  • PET waste polyethylene terephthalate
  • polyesters are widely used in many products for human consumption, among the best known polyesters is polyethylene terephthalate, better known as PET, which is a polyester saturated with terephthalic acid and ethylene glycol.
  • PET polyethylene terephthalate
  • the consumption of PET has had a great boom, particularly because this compound is used intensively in the manufacture of containers for various liquid products, including water and other bottled beverages.
  • the global PET consumption amounts to more than thirteen million tons of items in three major markets: textiles, video tapes and the packaging and container industry, where mainly bottles are manufactured drinks.
  • PET has been used particularly in the manufacture of bottles for beverages due to its characteristics of low weight, high resistance, low gas permeability and, above all, because PET has no harmful effects for human health .
  • glycolysis it consists of degrading the polyester by means of diols such as ethylene glycol at temperature conditions of between 180 ° to 250 ° C.
  • the method described in this document contemplates the use of a catalyst for the depolymerization of polyesters in ethylene glycol, the reaction takes place at a temperature between 175 ° to 190 ° C and pressures ranging from 1 to 5 atmospheres (0.1 to 0.5 MPa).
  • the polyester is degraded by alcohols, mainly methanol, where the depolymerization is carried out at temperature conditions between 200 ° and 300 ° C and with pressures that are between 2 to 300 atmospheres, which represents a disadvantage, since you need equipment that can withstand this pressure.
  • the main products obtained with this procedure are dimethyl terephthalate (DMT) and ethylene glycol (EG).
  • a methanolysis process can be found described in US Pat. No. 5,051,528 in which the PET is dissolved in oligomers of terephthalic acid and ethylene glycol and then treated with methanol, thus obtaining DMT and ethylene glycol. In relation to the depolymerization by hydrolysis, it breaks down the ester bond by means of OH ions.
  • alkaline or basic hydrolysis in which an alkali, typically NaOH, is used to decompose the polyester in an aqueous medium and the reaction is carried out at high temperatures and pressures; likewise, in other cases the reaction medium is ethylene glycol; ii) Neutral hydrolysis, in this variant the reaction is carried out using water at high temperatures; and iii) Acid hydrolysis, in which the polyester is decomposed using mainly concentrated sulfuric acid.
  • alkaline hydrolysis can be found in European Patent No. Serial No.
  • said document describes a method for the recovery of terephthalic acid from a pulverized waste PET product, which comprises; (a) a decomposition reaction step, where the pulverized waste PET products are subjected continuously to a decomposition reaction in ethylene glycol and in the presence of an alkali that is in an equimolar or excess proportion relative to the PET, such that the salt of terephthalic acid and ethylene glycol can be obtained continuously; (b) a solid-liquid separation step, dissolution and removal of impurities, where the ethylene glycol is separated from the terephthalic acid salt of the decay reaction of terephthalic acid and ethylene glycol, and the terephthalic acid salt is dissolved in water, while the insoluble impurities are removed; (c) a neutralization / crystallization step, wherein the solution of said terephthalic acid salt is neutralized with acid so that the terephthalic acid can be crystallized; (d) a solid-liquid washing
  • temperatures in the step of the decomposition reaction it is necessary to reach high temperatures, particularly in the order of between 130 ° and 180 ° C, and as can be seen from the examples included in the application, temperatures must be reached in the range of 180 ° to 190 ° C to promote the breakdown of PET chains. It is also important to note that prior to the decomposition reaction, it is contemplated to carry out a previous heating stage where the sprayed PET is heated at temperatures ranging from 100 ° to 140 ° C, or a thermal degradation stage carried out at temperatures of the order of 290 ° to 330 ° C. As can be seen, in these previous stages it is also necessary to reach high temperatures.
  • PET can be depolymerized by a saponification reaction carried out at temperatures defined by the boiling point of an alcoholic reaction medium, said temperatures being lower compared to those described in any of the depolymerization reactions of the prior art processes, said saponification step being carried out preferably at atmospheric pressure, it being possible also to perform it at higher pressures.
  • the saponification reaction can be followed by a series of steps in order to recover ethylene glycol, terephthalic acid or salts thereof, which are compounds of high commercial value.
  • the chemical waste PET recycling method which is described according to a particularly specific embodiment of the present invention, which should be considered as illustrative but not limiting thereof, comprises the steps of: a) A step of saponification reaction, in which waste PET particles are reacted with stoichiometric amounts, or, in excess, of a strong base of a metal in an alcoholic reaction medium, where the reaction is brought to the boiling temperature of the alcoholic reaction medium, obtaining as reaction products a salt of terephthalic acid with the metal of the base and ethylene glycol which is incorporated into the alcoholic reaction medium.
  • the stage of saponification reaction in which waste PET particles are reacted with stoichiometric amounts, or, in excess, of a strong base of a metal in an alcoholic reaction medium, where the reaction is brought to the boiling temperature of the alcoholic reaction medium, obtaining as reaction products a salt of terephthalic acid with the metal of the base and ethylene glycol which is incorporated into the alcoholic reaction medium.
  • the saponification reaction is carried out at atmospheric pressure, which can also be carried out at pressures greater than atmospheric pressure.
  • the waste PET particles are obtained from any source, such as used bottles and beverage containers, as well as they can be in any of their known forms, that is, in the form of film, fiber, and the like, etc.
  • the base that is used to react with the PET is selected from the group consisting of alkali metal hydroxides or alkaline earth metal hydroxides, sodium hydroxide (NaOH) being used in a preferred embodiment or potassium hydroxide (KOH).
  • the alcohol reaction medium in which the saponification reaction is carried out is essentially formed by: a monohydric or polyhydric alcohol, a mixture of monohydric alcohols, a mixture of polyhydric alcohols or a mixture of alcohols monohydric and polyhydric.
  • the alcoholic reaction medium is formed by a monohydric alcohol selected from alcohols of 1 to 8 carbon atoms, primary, secondary or tertiary, linear or branched, or a mixture thereof.
  • it is preferred to use as an alcoholic reaction medium a mixture of methanol / ethanol in a ratio of 20/80 by volume.
  • said separation step comprises the steps of: i) cooling the reaction mixture to a temperature lower than 90 ° C; ii) adding a sufficient amount of water to the reaction medium to dissolve the terephthalic acid salt, whereby two phases are formed, namely
  • aqueous phase in which the terephthalic acid salt is dissolved, and an organic phase consisting of the alcoholic reaction medium in which the ethylene glycol is incorporated; and, iii) a liquid-liquid separation step, in which the aqueous phase containing the terephthalic acid is separated from the organic phase.
  • said separated aqueous phase is subjected to stage (c) of formation of terephthalic acid, while the separated organic phase is subjected to step (e) of recovery of ethylene glycol.
  • the step of separating the terephthalic acid salt comprises the steps of: i) optionally cooling the reaction mixture of step (a) of saponification reaction; ii) filtering the reaction mixture to separate the crystals formed from the terephthalic acid salt of the alcohol reaction medium where the ethylene glycol is incorporated; and, iii) washing the separated crystals with an organic solvent to remove residues of the alcoholic medium and ethylene glycol that may be impregnated in the terephthalic acid salt.
  • the separated terephthalic acid salt is subjected to step (c) of formation of terephthalic acid, while the alcoholic medium where the ethylene glycol is incorporated is subjected to the step (e) of recovery thereof.
  • the solvent is selected from methanol, ethanol, acetone, dichloromethane, chloroform, or other volatile organic solvents miscible with the alcoholic reaction medium.
  • terephthalic acid is obtained which It can be used as raw material.
  • the reaction mixture was allowed to cool and 50 ml of water was added to the flask to dissolve the solids present (sodium terephthalate), then the contents of the flask was filtered to determine the amount of PET that did not react, which, in this case, it was null.
  • the filtered liquid, an aqueous phase and an organic phase was poured into a separation funnel, where both phases were separated.
  • concentrated hydrochloric acid was added to the aqueous phase until it reached an acid pH, precipitating the terephthalic acid, which was filtered, washed and dried, the weight of the product obtained indicated a 96% yield.
  • the product obtained was characterized by IR spectroscopy, its spectrum being identical to that reported in the literature for terephthalic acid.
  • Example 2 The procedure of Example 1 was repeated, but now using 20ml of ethylene glycol in the reaction, after having heated the mixture and maintained at a temperature of 183 ° C for 5 minutes, it was allowed to cool and the contents of the flask was filtered to Separate the ethylene glycol from the sodium terephthalate formed in the reaction. The precipitate (salt) was washed with ethanol to recover the ethylene glycol that was impregnated with the precipitate. The weight of sodium terephthalate was 3.2g, which indicates a 98% yield. Ethanol was evaporated to the washing liquid to recover the ethylene glycol that could be reused.
  • Example 3 The procedure of Example 1 was repeated again, but now using 20ml of hexanol, the mixture was heated and maintained at a temperature of 147 ° C for 15 minutes, then allowed to cool. The contents of the flask were filtered to separate the liquid phase of the sodium terephthalate formed, which was washed with acetone to recover the hexanol and ethylene glycol that were impregnated with the precipitate. The salt obtained was dissolved in water without residues of waste PET being observed. The acetone was evaporated to the washing liquid to recover hexanol and ethylene glycol.
  • EXAMPLE 4 In a ball flask, 1g of PET cut into small pieces and 0.5g of NaOH were reacted, using as reaction medium 10mi of 1- pentanol, the reaction temperature was 124 ° C, which temperature was maintained during 10 minutes. The reaction mixture was treated with 12 ml of water to dissolve the white precipitate formed (sodium terephthalate) whereby two phases, an organic phase and an aqueous phase were formed. Both phases were separated in a separatory funnel, the aqueous phase was subsequently filtered to eliminate the insoluble impurities. Once the aqueous phase was filtered, it was treated with sulfuric acid until obtaining an approximate pH of 2, managing to precipitate the terephthalic acid. The white precipitate obtained was filtered and washed with water to be subsequently dried. The weight of the terephthalic acid obtained was 0.83 g, indicating a 96% yield.
  • EXAMPLE 5 The procedure of Example 4 was repeated, but now using 7ml of 1-butanol in the saponification reaction, which was carried out at 108 ° C for 15 minutes. Once the terephthalic acid was crystallized and dried, 0.83g of this compound was obtained, that is, a 96% yield was obtained.
  • EXAMPLE 6 In a 500ml glass reactor, 30g of ground PET waste was reacted with 15g of NaOH in 150ml of 1-propanol at a temperature of 89 ° C for 15 minutes and maintaining vigorous mechanical agitation. The obtained reaction mixture was filtered on a mesh filter to remove residual particles. The filtered liquid was reacted with concentrated hydrochloric acid to form and precipitate the terephthalic acid, subsequently the mixture thus obtained was
  • PET residues were 1.1g indicating 96% conversion.
  • EXAMPLE 7 1g of PET was cut into small pieces, which were reacted for 5 minutes with 0.5g of NaOH and 7ml of a 1-pentanol / ethanol mixture 40/60 by volume, at 78 ° C. To the reaction mixture was added 12ml of water to dissolve the precipitate (sodium terephthalate), forming two phases. The resulting mixture was filtered and the residue was washed and dried in order to know the degree of conversion of PET. The PET residue weighed 0.02g indicating 98% conversion. The aqueous phase was treated with sulfuric acid, succeeding in precipitating the terephthalic acid, which was subsequently filtered, washed and weighed. The recovery of the terephthalic acid from the aqueous solution was greater than 95%.
  • EXAMPLE 8 The procedure of Example 7 was repeated, but now using 7ml of ethanol, the saponification reaction was performed at 73 ° C and for 15 minutes. At the end of the reaction water was added to dissolve the salt of formed terfetálico acid, later this mixture was filtered to separate the PET that did not react, that in this case were 0.31 g, indicating a 69% of conversion. The filtrate was subsequently treated with sulfuric acid to recover the terephthalic acid.
  • Example 9 The procedure of Example 7 was repeated again, but now using 7ml of methanol at 59 ° C for 20 minutes. At the end of the saponification reaction, water was added in an amount sufficient to dissolve the salt of terephthalic acid formed, subsequently the contents of the flask was filtered to separate the PET residues that did not react, which, in this case, weighed 0.25 g, indicating a 75% conversion. The filtrate was subsequently treated with sulfuric acid to recover the terephthalic acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Sustainable Development (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)
PCT/IB2004/000257 2004-01-27 2004-01-27 Procedimiento quimico de reciclado de polietilentereftalato (pet) de desecho Ceased WO2005082826A1 (es)

Priority Applications (12)

Application Number Priority Date Filing Date Title
JP2006550315A JP4647625B2 (ja) 2004-01-27 2004-01-27 廃棄ポリエチレンテレフタレート（ｐｅｔ）の化学的リサイクル手法
US10/587,518 US7893122B2 (en) 2004-01-27 2004-01-27 Chemical process for recycling polyethylene terephthalate (PET) waste
PCT/IB2004/000257 WO2005082826A1 (es) 2004-01-27 2004-01-27 Procedimiento quimico de reciclado de polietilentereftalato (pet) de desecho
KR1020067015142A KR100983349B1 (ko) 2004-01-27 2004-01-27 폴리에틸렌 테레프탈레이트 (ｐｅｔ) 폐기물의 화학적재활용 방법
AU2004316446A AU2004316446B2 (en) 2004-01-27 2004-01-27 Chemical method for recycling polyethylene terephtalate (PET) wastes
PT04705473T PT1710226E (pt) 2004-01-27 2004-01-27 Processo químico de reciclagem de resíduos de tereftalato de polietileno (pet)
EP04705473A EP1710226B1 (en) 2004-01-27 2004-01-27 Chemical method for recycling polyethylene terephtalate (pet) wastes
ES04705473T ES2328139T3 (es) 2004-01-27 2004-01-27 Procedimiento quimico para el reciclado de residuos de tereftalato de polietileno (pet).
DE602004022199T DE602004022199D1 (de) 2004-01-27 2004-01-27 Chemisches verfahren zum recycling von polyethylenterephtalat (pet)-abfällen
CA2595393A CA2595393C (en) 2004-01-27 2004-01-27 Chemical process for recycling polyethylene terephthalate (pet) wastes
DK04705473T DK1710226T3 (da) 2004-01-27 2004-01-27 Kemisk fremgangsmåde til genanvendelse af polyethylenterephthalataffald (PET)
IL176986A IL176986A (en) 2004-01-27 2006-07-20 Chemical process for recycling pet waste

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2004/000257 WO2005082826A1 (es) 2004-01-27 2004-01-27 Procedimiento quimico de reciclado de polietilentereftalato (pet) de desecho

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WO2005082826A1 true WO2005082826A1 (es) 2005-09-09

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PCT/IB2004/000257 Ceased WO2005082826A1 (es) 2004-01-27 2004-01-27 Procedimiento quimico de reciclado de polietilentereftalato (pet) de desecho

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Country Link
US (1) US7893122B2 (cg-RX-API-DMAC10.html)
EP (1) EP1710226B1 (cg-RX-API-DMAC10.html)
JP (1) JP4647625B2 (cg-RX-API-DMAC10.html)
KR (1) KR100983349B1 (cg-RX-API-DMAC10.html)
AU (1) AU2004316446B2 (cg-RX-API-DMAC10.html)
CA (1) CA2595393C (cg-RX-API-DMAC10.html)
DE (1) DE602004022199D1 (cg-RX-API-DMAC10.html)
DK (1) DK1710226T3 (cg-RX-API-DMAC10.html)
ES (1) ES2328139T3 (cg-RX-API-DMAC10.html)
IL (1) IL176986A (cg-RX-API-DMAC10.html)
PT (1) PT1710226E (cg-RX-API-DMAC10.html)
WO (1) WO2005082826A1 (cg-RX-API-DMAC10.html)

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WO2010101698A3 (en) * 2009-03-03 2011-02-24 The Coca-Cola Company Bio-based polyethylene terephthalate packaging and method of making thereof
WO2013111332A1 (ja) 2012-01-27 2013-08-01 株式会社ジナリス テレフタル酸カリウム塩からの有用化学品の製造法

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KR101283172B1 (ko) 2006-04-07 2013-07-08 킴벌리-클라크 월드와이드, 인크. 생분해성 부직 라미네이트
US8710172B2 (en) 2006-07-14 2014-04-29 Kimberly-Clark Worldwide, Inc. Biodegradable aliphatic-aromatic copolyester for use in nonwoven webs
KR101297937B1 (ko) 2006-07-14 2013-08-19 킴벌리-클라크 월드와이드, 인크. 부직 웹에 사용하기 위한 생분해성 지방족 폴리에스테르
WO2008008074A1 (en) 2006-07-14 2008-01-17 Kimberly-Clark Worldwide, Inc. Biodegradable polyactic acid for use in nonwoven webs
US8470222B2 (en) 2008-06-06 2013-06-25 Kimberly-Clark Worldwide, Inc. Fibers formed from a blend of a modified aliphatic-aromatic copolyester and thermoplastic starch
US8841386B2 (en) * 2008-06-10 2014-09-23 Kimberly-Clark Worldwide, Inc. Fibers formed from aromatic polyester and polyether copolymer
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US9458354B2 (en) 2010-10-06 2016-10-04 Resinate Technologies, Inc. Polyurethane dispersions and methods of making and using same
CA2838825A1 (en) 2011-06-10 2012-12-13 Kristopher M. Felice Clear coatings acrylic coatings
US10196496B2 (en) 2013-03-31 2019-02-05 Pranay Jain Process for recycling a metalized polyester film
BR102014029870B1 (pt) * 2014-11-28 2018-05-08 Univ Federal Do Espirito Santo Ufes resina supressora de pó de minérios e uso da resina
JP2018510225A (ja) 2015-01-30 2018-04-12 レジネート マテリアルズ グループ、インコーポレイテッド Ｐｅｔ及びｐｔｔのリサイクル流の統合処理方法
JP6671067B2 (ja) * 2015-04-10 2020-03-25 国立研究開発法人産業技術総合研究所 架橋化ｅｖａの可溶化方法、可溶化方法を用いた使用済み太陽電池からの資源回収法
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US9981902B2 (en) 2015-10-23 2018-05-29 Columbia Insurance Company Process for production of an ester and diol from reclaimed carpet material
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US10252976B1 (en) 2017-09-15 2019-04-09 9449710 Canada Inc. Terephthalic acid esters formation
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